pirazolo piridinas

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Acta Cryst. (1999). C55, IUC9900168 [ doi:10.1107/S0108270199098273 ]

Three 3-aryl-5-cyanopyrazolo[3,4-b]pyridines

J. Quiroga, S. Cruz, B. Insuasty, M. Nogueras, A. Sánchez, J. Cobo and J. N. Low

Abstract

4-(4-Chlorophenyl)-5-cyano-3-(4-methylphenyl)-6-diphenyl-4,7-dihydro-2 H - pyrazolo[3,4-b]pyridine–dimethyl formam-

ide (2/1), 2C26H19ClN4·C3H7 NO, (I), 5-cyano-4-(4-methoxyphenyl)-3,6-diphenyl-4,7-dihydro-2 H -pyrazolo[3,4-b]- pyrid-

ine, C26H20 N4O, (II), and 3,4-bis(4-chlorophenyl)-5-cyano-6-phenyl-1 H -pyrazolo[3,4-b]pyridine, C25H14Cl2 N4, (III),

were prepared from the corresponding 3-amino-5-arylpyrazoles and α-cyanochalcones. NMR solution studies (1 H , 13 C,

HSQC, HMBC, NOESY) of pyrazolo[3,4-b]pyridines, reveal the 2 H -tautomers as being preferred in solution (DMSO-d6).

X-ray diffraction studies showed that (I) and (II) also have the 2 H -tautomeric structures in the crystal structures. (III) is the

aromatic crystalline product formed by oxidation of a 2H precusor during re-crystallization. (I) exists as hydrogen-bonded

trimers (two pyrazolo[3,4-b]pyridine systems and a dimethyl formamide), (II) forms two-dimensional sheets and (III) is acentrosymmetric dimer. A paper discussing the chemistry of the above compounds is being prepared

Experimental

4-(4-Chlorophenyl)-5-cyano-3-(4-methylphenyl)-6-diphenyl-4,7-dihydro-2 H - pyrazolo[3,4-

b]pyridine–dimethylformamide (2/1), (I): a solution of 1.40 mmol of 3-amine-5-(4-methylphenyl)-1 H -pyrazole and 1.40

mmol of 2-benzoyl-3-(4-chlorophenyl)-2-propenenitrile was heated in 50 ml of absolute ethanol for 1–2 h. After cooling,

the reaction mixture was allowed to stand overnight. The resulting precipitate was filtered off, washed with cold ethanol

and recrystallized from dimethyl formamide.

5-Cyano-4-(4-methoxyphenyl)-3,6-diphenyl-4,7-dihydro-2 H -pyrazolo [3,4-b]pyridine, (II): a solution of 1.40 mmol of

3-amine-5-phenyl-1 H -pyrazole and 1.40 mmol of 2-benzoyl-3-(4-methoxyphenyl)-2-propenenitrile was heated in 50 ml of

absolute ethanol for 1–2 h. After cooling, the reaction mixture was allowed to stand overnight. The resulting precipitate was

filtered off, washed with cold ethanol and recrystallized from ethanol.

3,4-Bis(4-chlorophenyl)-5-cyano-6-phenyl-1 H -pyrazolo-[3,4-b]pyridine, (III): a solution of 1.40 mmol of 3-amine-5-(4-

chlorophenyl)-1 H -pyrazole and 1.40 mmol of 2-benzoyl-3-(4-chlorophenyl)-2-propenenitrile was heated in 50 ml of abso-

lute ethanol for 1–2 h. After cooling, the reaction mixture was allowed to stand overnight. The resulting precipitate was

filtered off, washed with cold ethanol and recrystallized from ethanol.

Refinement

Compound (I) crystallized in the triclinic system; space group P 1 assumed and confirmed by structure analysis. There are

two independent molecules of the 2 H -pyrazolo[3,4-b]pyridine derivative and one of the crystallization solvent (dimethyl

formamide) in the asymmetric unit. Molecule (II) crystallized in the monoclinic system; space group C 2/c or Cc from

systematic absences; C 2/c chosen and confirmed by the analysis. Molecule (III) crystallized in the monoclinic system; space

group P 21/n from systematic absences. In all structures, H atoms were treated as riding atoms with C—H 0.95–1.00 Å,

http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Low,%20J.N.

http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Cobo,%20J.

http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=S%26aacute;nchez,%20A.

http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Nogueras,%20M.

http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Insuasty,%20B.

http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Cruz,%20S.

http://scripts.iucr.org/cgi-bin/citedin?search_on=name&author_name=Quiroga,%20J.

http://dx.doi.org/10.1107/S0108270199098273



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N—H 0.88 Å. Examination of the structures with PLATON (Spek, 1999) showed that there were no solvent-accessible voids

in the crystal lattices.

Computing details

For all compounds, data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO (Otwinowski& Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure:

SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics:

ORTEPII (Johnson, 1976) and PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97 and

WORDPERFECT macro PRPKAPPA (Ferguson, 1999)

4-(4-chlorophenyl)-5-cyano-3-(4-methylphenyl)-6-diphenyl-4,7-dihydro-2H -pyrazolo [3,4-b]pyridine:dimethylformamide (2/1)

Crystal data

2C26H19ClN4·C3H7 NO γ = 99.610 (2)º

M r = 918.90 V = 2322.64 (15) Å3

Triclinic, P 1 Z = 2

a = 12.4124 (5) Å Mo K α

b = 13.8275 (4) Å µ = 0.19 mm−1

c = 14.3744 (6) Å T = 150.0 (1) K

α = 91.747 (2)º 0.2 × 0.2 × 0.15 mm

β = 106.6376 (17)º

Data collection

KappaCCDdiffractometer

10310 independent reflections

Absorption correction: Multi-scan(SORTAV; Blessing, 1995, 1997)

4898 reflections with I > 2σ( I )

T min = 0.963, T max = 0.971 Rint = 0.112

36207 measured reflections

Refinement

R[ F 2 > 2σ( F 2)] = 0.062 606 parameters

wR( F 2) = 0.162 H-atom parameters constrained

S = 0.93 Δρmax = 0.49 e Å−3

10310 reflections Δρmin = −0.38 e Å−3

5-Cyano-4-(4-methoxyphenyl)-3,6-diphenyl-4,7-dihydro-2H -pyrazolo- [3,4-b]pyridine



CIF access

Crystal data

C26H20 N4O V = 4106.04 (13) Å3

M r = 404.46 Z = 8

Monoclinic, C 2/c Mo K α

a = 15.6264 (3) Å µ = 0.08 mm−1

b = 12.4397 (2) Å T = 150.0 (1) K

c = 21.1296 (4) Å 0.15 × 0.15 × 0.12 mm

β = 91.4371 (9)º

Data collection





T min

= 0.988, T max

= 0.990 Rint

= 0.072


Refinement

R[ F 2 > 2σ( F 2)] = 0.048 282 parameters


S = 1.06 Δρmax = 0.39 e Å−3


3,4-Bis(4-chlorophenyl)-5-cyano-6-phenyl-1H -pyrazolo-[3,4-b]pyridine

Crystal data

C25H14Cl2 N4 V = 2061.3 (3) Å3

M r = 441.30 Z = 4

Monoclinic, P 21/n Mo K α

a = 6.6222 (5) Å µ = 0.34 mm−1

b = 11.0791 (10) Å T = 150.0 (1) K

c = 28.264 (2) Å 0.10 × 0.10 × 0.05 mm

β = 96.248 (5)º

Data collection





T min = 0.967, T max = 0.983 Rint = 0.047




CIF access

Refinement

R[ F 2 > 2σ( F 2)] = 0.058 280 parameters


S = 0.94 Δρmax = 0.40 e Å−3


Acknowledgements

X-ray data were collected at the EPSRC, X-ray Crystallographic Service, University of Southampton, using a Enraf–Nonius

KappaCCD diffractometer. The authors thank the staff for all their help and advice.

References

Blessing, R. H. (1995). Acta Cryst. A51, 33–38.

Blessing, R. H. (1997). J. Appl. Cryst. 30, 421–426.

Ferguson, G. (1999). PRPKAPPA. A WORDPERFECT5.1 macro to formulate and polish CIF format files from the

SHELXL97 refinement of KappaCCD data. University of Guelph, Canada.

Johnson, C. K. (1976). ORTEPII . Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.

Nonius (1997). KappaCCD Server Software. Windows 3.11 Version. Nonius BV, Delft, The Netherlands.

Otwinowski, Z. & Minor, W. (1997). Methods Enzymol. 276, 307–326.

Sheldrick, G. M. (1997a). SHELXS97 . Program for the solution of crystal structures. University of Göttingen, Germany.

Sheldrick, G. M. (1997b). SHELXL97 . Program for the refinement of crystal structures. University of Göttingen, Germany.

Spek, A. L. (1999). PLATON . Molecular Geometry and Graphics Program. January 1999 version. University of Utrecht,

The Netherlands.



CIF access

Scheme 1



supplementary materials




sup-1

4-(4-chlorophenyl)-5-cyano-3-(4-methylphenyl)-6-diphenyl-4,7-dihydro-2H -pyrazolo [3,4-b]pyridine:dimethylformamide (2/1)

Crystal data

2C26H19ClN4·C3H7 NO Z = 2

M r = 918.90 F 000 = 960

Triclinic, P 1 Dx = 1.314 Mg m−3

a = 12.4124 (5) ÅMo K α radiationλ = 0.71073 Å

b = 13.8275 (4) Å Cell parameters from 25 reflections

c = 14.3744 (6) Å θ = 1.5–27.3º

α = 91.747 (2)º µ = 0.19 mm−1

β = 106.6376 (17)º T = 150.0 (1) K

γ = 99.610 (2)º Block, colourless

V = 2322.64 (15) Å

3 0.2 × 0.2 × 0.15 mm

Data collection



Radiation source: fine-focus sealed X-ray tube 4898 reflections with I > 2σ( I )

Monochromator: graphite Rint = 0.112

T = 150.0(1) K θmax = 27.3º

φ scans and ω scans with κ offsets θmin = 1.5º


h = −16→16

T min = 0.963, T max = 0.971 k = −17→1736207 measured reflections l = −18→18

Refinement

Refinement on F 2 Secondary atom site location: difference Fourier map

Least-squares matrix: fullHydrogen site location: inferred from neighbouringsites

R[ F 2 > 2σ( F 2)] = 0.062 H-atom parameters constrained

wR( F 2) = 0.162w = 1/[σ2( F o

2) + (0.0726 P )2]

where P = ( F o2 + 2 F c

2)/3 ?

S = 0.93 (Δ/σ)max = 0.00210310 reflections Δρmax = 0.49 e Å−3

606 parameters Δρmin = −0.38 e Å−3

Primary atom site location: structure-invariant directmethods

Extinction correction: none




sup-2

Special details

Experimental. KappaCCD diffractometer using the following programs. Collect: Data collection software, Hooft, 1998 [Hooft, R.

(1998). Nonius BV, Delft, The Netherlands], is a graphical user interface written by Enraf–Nonius which encompasses the following

programs. DENZO (Otwinowski and Minor, 1997) and indexing and data collection software package and a scaling package, SCALE-

PACK both of which programs are produced by the company HKL. Absorption corrections are performed by the SORTAV package,

Blessing, 1995 and Blessing, 1997. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used.

No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental

table are calculated from the 'size' command in the SHELXL97 input file. Low temperature data is collected using an Oxford Cryosys-

tems cryostream [Cosier, J. & Glazer, A· M . (1986). J. Appl. Cryst. 19, 105–107]. The Rint value for this compound is 0.112 which is

greater than 0.10. However, the R-factor for the "greater than" reflections is 0.0616 whereas that for all data is 0.1599 this suggests that

the high Rint results from discrepancies in the values of the weak reflections.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2 )

x y z U iso*/U eq

N11 0.31279 (19) 0.46649 (15) −0.07395 (18) 0.0280 (6)

N21 0.34303 (19) 0.55473 (15) −0.02102 (18) 0.0287 (6)

C31 0.4301 (2) 0.61564 (19) −0.0403 (2) 0.0262 (7)

C311 0.4732 (2) 0.71532 (19) 0.0082 (2) 0.0268 (7)

C321 0.5823 (2) 0.7640 (2) 0.0147 (2) 0.0316 (7)

C331 0.6213 (3) 0.8595 (2) 0.0555 (2) 0.0359 (8)

C341 0.5527 (3) 0.9095 (2) 0.0936 (2) 0.0338 (7)

C351 0.4443 (3) 0.8603 (2) 0.0891 (2) 0.0349 (8)

C361 0.4051 (3) 0.7650 (2) 0.0475 (2) 0.0322 (7)

C371 0.5969 (3) 1.0134 (2) 0.1392 (3) 0.0456 (9)

C7A1 0.3830 (2) 0.47397 (19) −0.1286 (2) 0.0278 (7)

C41 0.5465 (2) 0.58653 (18) −0.1661 (2) 0.0275 (7)C411 0.5450 (2) 0.68439 (19) −0.2123 (2) 0.0280 (7)

C421 0.4438 (3) 0.7074 (2) −0.2688 (2) 0.0346 (8)

C431 0.4414 (3) 0.7963 (2) −0.3106 (2) 0.0390 (8)

C441 0.5417 (3) 0.8627 (2) −0.2946 (3) 0.0409 (9)

C451 0.6431 (3) 0.8425 (2) −0.2390 (3) 0.0447 (9)

C461 0.6446 (3) 0.7525 (2) −0.1981 (3) 0.0375 (8)

Cl41 0.53772 (9) 0.97578 (6) −0.34479 (8) 0.0637 (3)

C51 0.5276 (2) 0.5012 (2) −0.2427 (2) 0.0296 (7)

C511 0.6063 (3) 0.5127 (2) −0.2997 (2) 0.0332 (8)

N521 0.6725 (2) 0.52741 (19) −0.3417 (2) 0.0463 (8)

C61 0.4477 (3) 0.4178 (2) −0.2576 (2) 0.0299 (7)

C611 0.4243 (2) 0.3383 (2) −0.3364 (2) 0.0300 (7)

C621 0.4176 (3) 0.3599 (2) −0.4316 (2) 0.0351 (8)

C631 0.3888 (3) 0.2849 (2) −0.5055 (3) 0.0423 (8)

C641 0.3651 (3) 0.1881 (2) −0.4850 (3) 0.0427 (9)

C651 0.3701 (3) 0.1659 (2) −0.3912 (3) 0.0422 (9)

C661 0.4006 (3) 0.2402 (2) −0.3168 (2) 0.0377 (8)

C3A1 0.4588 (2) 0.56355 (19) −0.1120 (2) 0.0266 (7)

N71 0.3783 (2) 0.40074 (16) −0.19817 (18) 0.0305 (6)




sup-3

N12 0.1797 (2) 0.51925 (15) 0.07986 (18) 0.0282 (6)

N22 0.1445 (2) 0.55577 (15) 0.15250 (18) 0.0295 (6)

C32 0.0585 (2) 0.49352 (19) 0.1717 (2) 0.0263 (7)

C312 0.0135 (2) 0.51872 (18) 0.2515 (2) 0.0257 (7)

C322 0.0825 (3) 0.5807 (2) 0.3328 (2) 0.0310 (7)

C332 0.0394 (3) 0.6072 (2) 0.4063 (2) 0.0339 (8)

C342 −0.0738 (3) 0.5720 (2) 0.4034 (2) 0.0310 (7)

C352 −0.1407 (3) 0.5088 (2) 0.3235 (2) 0.0333 (8)

C362 −0.0989 (2) 0.48183 (19) 0.2487 (2) 0.0300 (7)

C372 −0.1206 (3) 0.6026 (2) 0.4829 (2) 0.0425 (9)

C3A2 0.0344 (2) 0.41129 (18) 0.1070 (2) 0.0251 (7)

C42 −0.0488 (2) 0.31540 (18) 0.0912 (2) 0.0242 (7)

C412 −0.0381 (2) 0.26407 (18) 0.1852 (2) 0.0244 (7)

C422 0.0685 (3) 0.2586 (2) 0.2464 (2) 0.0327 (7)

C432 0.0807 (3) 0.2119 (2) 0.3319 (2) 0.0400 (8)

C442 −0.0147 (3) 0.1707 (2) 0.3559 (2) 0.0379 (8)

C452 −0.1220 (3) 0.1747 (2) 0.2960 (3) 0.0396 (8)

C462 −0.1334 (3) 0.22141 (19) 0.2107 (2) 0.0321 (7)Cl42 0.00113 (10) 0.11313 (6) 0.46311 (7) 0.0646 (3)

C52 −0.0281 (2) 0.24955 (18) 0.0122 (2) 0.0244 (7)

C512 −0.1041 (2) 0.1571 (2) −0.0123 (2) 0.0277 (7)

N522 −0.1683 (2) 0.08371 (18) −0.0277 (2) 0.0382 (7)

C62 0.0518 (2) 0.27491 (18) −0.0354 (2) 0.0252 (7)

C612 0.0695 (2) 0.21027 (18) −0.1127 (2) 0.0251 (7)

C622 0.0679 (2) 0.11017 (19) −0.1040 (2) 0.0302 (7)

C632 0.0832 (3) 0.0522 (2) −0.1778 (2) 0.0360 (8)

C642 0.1025 (3) 0.0926 (2) −0.2588 (2) 0.0395 (8)

C652 0.1062 (3) 0.1925 (2) −0.2675 (2) 0.0368 (8)

C662 0.0894 (2) 0.2508 (2) −0.1952 (2) 0.0308 (7)

N72 0.12093 (19) 0.36584 (15) −0.01714 (18) 0.0289 (6)

C7A2 0.1117 (2) 0.43158 (18) 0.0537 (2) 0.0255 (7)

O1 0.2528 (2) 0.74772 (17) 0.2201 (2) 0.0687 (8)

C1 0.2233 (3) 0.8115 (3) 0.2624 (3) 0.0577 (10)

N2 0.2561 (2) 0.8325 (2) 0.3582 (2) 0.0507 (8)

C3 0.2105 (4) 0.9052 (4) 0.4003 (5) 0.131 (3)

C4 0.3332 (4) 0.7776 (4) 0.4202 (4) 0.0940 (16)

H21 0.3101 0.5706 0.0208 0.034*

H321 0.6303 0.7317 −0.0088 0.038*

H331 0.6944 0.8910 0.0577 0.043*

H351 0.3973 0.8921 0.1146 0.042*

H361 0.3321 0.7334 0.0455 0.039*H37A 0.6561 1.0441 0.1132 0.068*

H37B 0.6272 1.0125 0.2085 0.068*

H37C 0.5355 1.0499 0.1248 0.068*

H41 0.6223 0.5898 −0.1194 0.033*

H421 0.3760 0.6624 −0.2791 0.042*

H431 0.3728 0.8109 −0.3489 0.047*

H451 0.7104 0.8881 −0.2284 0.054*

H461 0.7137 0.7379 −0.1608 0.045*




sup-4

H621 0.4325 0.4251 −0.4457 0.042*

H631 0.3855 0.2998 −0.5688 0.051*

H641 0.3456 0.1379 −0.5346 0.051*

H651 0.3530 0.1006 −0.3779 0.051*

H661 0.4052 0.2246 −0.2534 0.045*

H71 0.3326 0.3453 −0.2042 0.037*

H22 0.1738 0.6127 0.1833 0.035*

H322 0.1586 0.6045 0.3373 0.037*

H332 0.0869 0.6495 0.4591 0.041*

H352 −0.2162 0.4835 0.3199 0.040*

H362 −0.1462 0.4389 0.1964 0.036*

H37D −0.1440 0.6650 0.4711 0.064*

H37E −0.0626 0.6081 0.5445 0.064*

H37F −0.1853 0.5541 0.4840 0.064*

H42 −0.1266 0.3291 0.0673 0.029*

H422 0.1334 0.2869 0.2301 0.039*

H432 0.1531 0.2086 0.3724 0.048*

H452 −0.1866 0.1463 0.3126 0.048*H462 −0.2060 0.2241 0.1702 0.039*

H622 0.0566 0.0822 −0.0487 0.036*

H632 0.0803 −0.0150 −0.1724 0.043*

H642 0.1132 0.0530 −0.3077 0.047*

H652 0.1200 0.2203 −0.3221 0.044*

H662 0.0914 0.3178 −0.2015 0.037*

H72 0.1693 0.3819 −0.0491 0.035*

H1 0.1739 0.8485 0.2246 0.069*

H3A 0.1678 0.9396 0.3496 0.196*

H3B 0.2720 0.9512 0.4441 0.196*

H3C 0.1611 0.8738 0.4355 0.196*

H4A 0.3660 0.7407 0.3813 0.141*

H4B 0.2918 0.7332 0.4535 0.141*

H4C 0.3929 0.8223 0.4671 0.141*

Atomic displacement parameters (Å2 )

U 11 U 22 U 33 U 12 U 13 U 23

N11 0.0314 (15) 0.0279 (13) 0.0242 (15) 0.0022 (11) 0.0092 (13) 0.0005 (11)

N21 0.0318 (14) 0.0292 (13) 0.0264 (16) 0.0034 (11) 0.0123 (13) −0.0011 (11)

C31 0.0247 (16) 0.0281 (15) 0.0246 (18) 0.0018 (13) 0.0068 (14) 0.0064 (13)

C311 0.0305 (17) 0.0265 (15) 0.0221 (18) 0.0028 (13) 0.0071 (14) 0.0037 (13)

C321 0.0278 (18) 0.0361 (17) 0.029 (2) 0.0032 (14) 0.0080 (15) −0.0016 (14)C331 0.0325 (18) 0.0355 (17) 0.035 (2) −0.0074 (14) 0.0101 (16) 0.0002 (15)

C341 0.0393 (19) 0.0320 (16) 0.027 (2) 0.0026 (14) 0.0075 (16) 0.0007 (14)

C351 0.0367 (19) 0.0334 (17) 0.037 (2) 0.0069 (14) 0.0147 (17) −0.0005 (14)

C361 0.0280 (17) 0.0362 (17) 0.031 (2) 0.0018 (14) 0.0098 (16) 0.0017 (14)

C371 0.053 (2) 0.0333 (17) 0.046 (2) −0.0018 (15) 0.0146 (19) −0.0071 (16)

C7A1 0.0319 (18) 0.0296 (16) 0.0240 (19) 0.0098 (13) 0.0086 (15) 0.0067 (13)

C41 0.0275 (17) 0.0287 (15) 0.0272 (19) 0.0039 (13) 0.0100 (15) 0.0032 (13)




sup-5

C411 0.0343 (18) 0.0283 (15) 0.0264 (19) 0.0045 (13) 0.0175 (16) 0.0024 (13)

C421 0.0341 (19) 0.0318 (16) 0.037 (2) 0.0002 (14) 0.0124 (17) 0.0035 (14)

C431 0.043 (2) 0.0388 (18) 0.040 (2) 0.0116 (16) 0.0169 (18) 0.0096 (16)

C441 0.058 (2) 0.0267 (16) 0.050 (2) 0.0115 (16) 0.033 (2) 0.0051 (15)

C451 0.050 (2) 0.0313 (17) 0.058 (3) −0.0049 (16) 0.031 (2) 0.0027 (16)

C461 0.0355 (19) 0.0359 (17) 0.044 (2) 0.0044 (15) 0.0172 (17) 0.0054 (15)

Cl41 0.0933 (8) 0.0334 (5) 0.0865 (9) 0.0203 (5) 0.0543 (7) 0.0227 (5)

C51 0.0339 (18) 0.0317 (16) 0.028 (2) 0.0095 (14) 0.0137 (16) 0.0088 (14)

C511 0.0375 (19) 0.0290 (16) 0.035 (2) 0.0112 (14) 0.0104 (17) 0.0039 (14)

N521 0.0484 (19) 0.0501 (17) 0.051 (2) 0.0153 (14) 0.0272 (17) 0.0123 (15)

C61 0.0363 (18) 0.0284 (16) 0.028 (2) 0.0121 (14) 0.0104 (16) 0.0061 (14)

C611 0.0336 (18) 0.0298 (16) 0.031 (2) 0.0125 (13) 0.0131 (15) 0.0058 (14)

C621 0.042 (2) 0.0329 (16) 0.033 (2) 0.0099 (14) 0.0138 (17) 0.0034 (15)

C631 0.052 (2) 0.044 (2) 0.032 (2) 0.0140 (17) 0.0123 (18) 0.0025 (16)

C641 0.053 (2) 0.0384 (19) 0.037 (2) 0.0117 (16) 0.0135 (19) −0.0102 (16)

C651 0.053 (2) 0.0287 (17) 0.044 (2) 0.0104 (15) 0.0112 (19) −0.0009 (16)

C661 0.050 (2) 0.0342 (17) 0.035 (2) 0.0160 (15) 0.0156 (18) 0.0067 (15)

C3A1 0.0299 (17) 0.0261 (15) 0.0243 (19) 0.0054 (13) 0.0081 (15) 0.0050 (13) N71 0.0418 (16) 0.0231 (12) 0.0279 (16) 0.0016 (11) 0.0151 (13) 0.0004 (11)

N12 0.0345 (15) 0.0236 (12) 0.0277 (16) 0.0025 (11) 0.0129 (13) −0.0009 (11)

N22 0.0385 (15) 0.0218 (12) 0.0297 (16) 0.0032 (11) 0.0145 (13) −0.0024 (11)

C32 0.0280 (17) 0.0227 (14) 0.0309 (19) 0.0067 (13) 0.0114 (15) 0.0057 (13)

C312 0.0305 (18) 0.0202 (14) 0.0282 (19) 0.0050 (13) 0.0111 (15) 0.0033 (13)

C322 0.0298 (17) 0.0336 (16) 0.031 (2) 0.0042 (13) 0.0125 (16) 0.0018 (14)

C332 0.039 (2) 0.0302 (16) 0.030 (2) 0.0021 (14) 0.0100 (16) −0.0052 (14)

C342 0.0371 (19) 0.0272 (15) 0.033 (2) 0.0079 (14) 0.0162 (17) 0.0030 (14)

C352 0.0301 (18) 0.0308 (16) 0.043 (2) 0.0079 (14) 0.0164 (17) 0.0075 (15)

C362 0.0354 (19) 0.0232 (14) 0.032 (2) 0.0052 (13) 0.0106 (16) 0.0009 (13)

C372 0.055 (2) 0.0413 (18) 0.039 (2) 0.0150 (16) 0.0225 (19) 0.0032 (16)

C3A2 0.0284 (17) 0.0213 (14) 0.0271 (19) 0.0052 (12) 0.0098 (14) 0.0052 (13)

C42 0.0253 (16) 0.0241 (14) 0.0243 (18) 0.0055 (12) 0.0086 (14) 0.0018 (12)

C412 0.0291 (17) 0.0187 (13) 0.0270 (19) 0.0028 (12) 0.0121 (15) 0.0000 (12)

C422 0.0335 (19) 0.0352 (16) 0.032 (2) 0.0053 (14) 0.0145 (16) 0.0077 (14)

C432 0.044 (2) 0.0373 (17) 0.036 (2) 0.0100 (15) 0.0067 (17) 0.0069 (16)

C442 0.060 (2) 0.0249 (16) 0.028 (2) −0.0002 (15) 0.0165 (19) 0.0061 (14)

C452 0.050 (2) 0.0310 (16) 0.040 (2) −0.0065 (15) 0.025 (2) 0.0009 (15)

C462 0.0324 (18) 0.0270 (15) 0.036 (2) −0.0013 (13) 0.0123 (16) 0.0008 (14)

Cl42 0.1069 (8) 0.0481 (5) 0.0314 (6) −0.0044 (5) 0.0186 (6) 0.0122 (4)

C52 0.0259 (16) 0.0227 (14) 0.0227 (18) 0.0014 (12) 0.0058 (14) 0.0027 (12)

C512 0.0314 (18) 0.0283 (16) 0.0267 (19) 0.0084 (14) 0.0119 (15) 0.0048 (13)

N522 0.0399 (16) 0.0302 (14) 0.045 (2) 0.0010 (13) 0.0161 (15) 0.0019 (12)C62 0.0306 (17) 0.0202 (14) 0.0234 (18) 0.0048 (12) 0.0055 (15) 0.0026 (12)

C612 0.0251 (16) 0.0225 (14) 0.0254 (18) 0.0023 (12) 0.0055 (14) −0.0003 (12)

C622 0.0349 (18) 0.0266 (15) 0.032 (2) 0.0048 (13) 0.0138 (16) 0.0064 (14)

C632 0.044 (2) 0.0240 (15) 0.039 (2) 0.0076 (14) 0.0107 (17) −0.0007 (14)

C642 0.053 (2) 0.0346 (18) 0.033 (2) 0.0082 (15) 0.0160 (18) −0.0036 (15)

C652 0.047 (2) 0.0358 (17) 0.029 (2) 0.0062 (15) 0.0152 (17) 0.0016 (15)

C662 0.0371 (18) 0.0247 (15) 0.029 (2) 0.0039 (13) 0.0092 (16) 0.0019 (13)

N72 0.0340 (15) 0.0244 (12) 0.0300 (16) −0.0019 (11) 0.0162 (13) −0.0005 (11)




sup-6

C7A2 0.0310 (17) 0.0190 (14) 0.0265 (19) 0.0041 (12) 0.0090 (15) 0.0019 (12)

O1 0.088 (2) 0.0402 (14) 0.077 (2) −0.0195 (13) 0.0438 (19) −0.0199 (14)

C1 0.056 (3) 0.048 (2) 0.053 (3) −0.0123 (19) 0.003 (2) 0.006 (2)

N2 0.0447 (18) 0.0542 (18) 0.047 (2) −0.0060 (14) 0.0138 (17) −0.0143 (16)

C3 0.086 (4) 0.111 (4) 0.200 (7) −0.023 (3) 0.082 (5) −0.078 (4)

C4 0.063 (3) 0.125 (4) 0.068 (4) −0.016 (3) −0.005 (3) 0.027 (3)

Geometric parameters (Å, °)

N11—C7A1 1.324 (3) N22—C32 1.353 (3)

N11—N21 1.355 (3) C32—C3A2 1.382 (4)

N21—C31 1.355 (3) C32—C312 1.469 (4)

C31—C3A1 1.399 (4) C312—C362 1.392 (4)

C31—C311 1.468 (4) C312—C322 1.398 (4)

C311—C321 1.384 (4) C322—C332 1.380 (4)

C311—C361 1.397 (4) C332—C342 1.397 (4)

C321—C331 1.377 (4) C342—C352 1.387 (4)

C331—C341 1.393 (4) C342—C372 1.502 (4)C341—C351 1.386 (4) C352—C362 1.386 (4)

C341—C371 1.506 (4) C3A2—C7A2 1.389 (4)

C351—C361 1.379 (4) C3A2—C42 1.505 (4)

C7A1—N71 1.384 (4) C42—C412 1.527 (4)

C7A1—C3A1 1.393 (4) C42—C52 1.539 (4)

C41—C3A1 1.508 (4) C412—C422 1.379 (4)

C41—C411 1.526 (3) C412—C462 1.382 (4)

C41—C51 1.530 (4) C422—C432 1.388 (4)

C411—C421 1.380 (4) C432—C442 1.366 (4)

C411—C461 1.383 (4) C442—C452 1.375 (5)

C421—C431 1.386 (4) C442—Cl42 1.732 (3)

C431—C441 1.374 (4) C452—C462 1.385 (4)C441—C451 1.363 (5) C52—C62 1.365 (4)

C441—Cl41 1.744 (3) C52—C512 1.424 (4)

C451—C461 1.393 (4) C512—N522 1.153 (3)

C51—C61 1.358 (4) C62—N72 1.370 (3)

C51—C511 1.437 (4) C62—C612 1.491 (4)

C511—N521 1.148 (3) C612—C622 1.391 (3)

C61—N71 1.375 (3) C612—C662 1.394 (4)

C61—C611 1.485 (4) C622—C632 1.386 (4)

C611—C621 1.391 (4) C632—C642 1.371 (4)

C611—C661 1.395 (4) C642—C652 1.386 (4)

C621—C631 1.387 (4) C652—C662 1.380 (4)

C631—C641 1.381 (4) N72—C7A2 1.387 (3)

C641—C651 1.378 (5) O1—C1 1.218 (4)

C651—C661 1.384 (4) C1—N2 1.327 (5)

N12—C7A2 1.332 (3) N2—C3 1.431 (5)

N12—N22 1.356 (3) N2—C4 1.442 (5)

C7A1—N11—N21 103.1 (2) N22—C32—C3A2 106.2 (2)

N11—N21—C31 113.6 (2) N22—C32—C312 120.8 (3)

N21—C31—C3A1 105.7 (2) C3A2—C32—C312 133.0 (3)




sup-7

N21—C31—C311 121.6 (2) C362—C312—C322 117.9 (3)

C3A1—C31—C311 132.7 (2) C362—C312—C32 121.2 (3)

C321—C311—C361 117.7 (3) C322—C312—C32 120.9 (3)

C321—C311—C31 121.0 (2) C332—C322—C312 121.1 (3)

C361—C311—C31 121.3 (3) C322—C332—C342 121.4 (3)

C331—C321—C311 121.3 (3) C352—C342—C332 116.9 (3)

C321—C331—C341 121.0 (3) C352—C342—C372 121.9 (3)

C351—C341—C331 118.0 (3) C332—C342—C372 121.1 (3)

C351—C341—C371 121.6 (3) C362—C352—C342 122.3 (3)

C331—C341—C371 120.4 (3) C352—C362—C312 120.3 (3)

C361—C351—C341 121.0 (3) C32—C3A2—C7A2 104.2 (2)

C351—C361—C311 121.0 (3) C32—C3A2—C42 133.3 (3)

N11—C7A1—N71 122.8 (2) C7A2—C3A2—C42 122.5 (2)

N11—C7A1—C3A1 113.8 (3) C3A2—C42—C412 112.0 (2)

N71—C7A1—C3A1 123.3 (3) C3A2—C42—C52 108.3 (2)

C3A1—C41—C411 113.6 (2) C412—C42—C52 111.1 (2)

C3A1—C41—C51 108.4 (2) C422—C412—C462 118.4 (3)

C411—C41—C51 111.1 (2) C422—C412—C42 120.0 (2)C421—C411—C461 118.3 (3) C462—C412—C42 121.6 (3)

C421—C411—C41 120.7 (3) C412—C422—C432 121.2 (3)

C461—C411—C41 121.0 (3) C442—C432—C422 119.3 (3)

C411—C421—C431 121.1 (3) C432—C442—C452 120.6 (3)

C441—C431—C421 119.2 (3) C432—C442—Cl42 119.1 (3)

C451—C441—C431 121.2 (3) C452—C442—Cl42 120.3 (2)

C451—C441—Cl41 119.8 (3) C442—C452—C462 119.6 (3)

C431—C441—Cl41 119.0 (3) C412—C462—C452 120.8 (3)

C441—C451—C461 119.1 (3) C62—C52—C512 120.4 (3)

C411—C461—C451 121.1 (3) C62—C52—C42 125.4 (2)

C61—C51—C511 119.6 (3) C512—C52—C42 114.2 (2)

C61—C51—C41 125.8 (3) N522—C512—C52 175.8 (3)

C511—C51—C41 114.5 (2) C52—C62—N72 121.3 (2)

N521—C511—C51 175.7 (3) C52—C62—C612 124.4 (2)

C51—C61—N71 120.8 (3) N72—C62—C612 114.3 (2)

C51—C61—C611 125.6 (3) C622—C612—C662 118.9 (3)

N71—C61—C611 113.6 (2) C622—C612—C62 121.5 (2)

C621—C611—C661 118.9 (3) C662—C612—C62 119.6 (2)

C621—C611—C61 121.2 (2) C632—C622—C612 119.9 (3)

C661—C611—C61 119.7 (3) C642—C632—C622 120.8 (3)

C631—C621—C611 120.5 (3) C632—C642—C652 119.8 (3)

C641—C631—C621 119.9 (3) C662—C652—C642 119.9 (3)

C651—C641—C631 120.2 (3) C652—C662—C612 120.6 (3)C641—C651—C661 120.2 (3) C62—N72—C7A2 118.9 (2)

C651—C661—C611 120.3 (3) N12—C7A2—N72 122.8 (2)

C7A1—C3A1—C31 103.8 (2) N12—C7A2—C3A2 113.5 (2)

C7A1—C3A1—C41 122.2 (3) N72—C7A2—C3A2 123.7 (2)

C31—C3A1—C41 134.0 (2) O1—C1—N2 125.2 (4)

C61—N71—C7A1 119.1 (2) C1—N2—C3 120.3 (4)

C7A2—N12—N22 102.9 (2) C1—N2—C4 119.5 (3)

C32—N22—N12 113.2 (2) C3—N2—C4 120.0 (4)




sup-8

C7A1—N11—N21—C31 −0.7 (3) N12—N22—C32—C3A2 −0.8 (3)

N11—N21—C31—C3A1 0.4 (3) N12—N22—C32—C312 176.9 (2)

N11—N21—C31—C311 178.6 (2) N22—C32—C312—C362 152.4 (3)

N21—C31—C311—C321 157.9 (3) C3A2—C32—C312—C362 −30.6 (5)

C3A1—C31—C311—C321 −24.4 (5) N22—C32—C312—C322 −27.6 (4)

N21—C31—C311—C361 −23.5 (4) C3A2—C32—C312—C322 149.4 (3)

C3A1—C31—C311—C361 154.3 (3) C362—C312—C322—C332 −2.2 (4)

C361—C311—C321—C331 −2.2 (4) C32—C312—C322—C332 177.8 (2)

C31—C311—C321—C331 176.5 (3) C312—C322—C332—C342 1.1 (4)

C311—C321—C331—C341 1.4 (5) C322—C332—C342—C352 0.4 (4)

C321—C331—C341—C351 0.0 (5) C322—C332—C342—C372 −179.0 (3)

C321—C331—C341—C371 179.2 (3) C332—C342—C352—C362 −0.8 (4)

C331—C341—C351—C361 −0.6 (5) C372—C342—C352—C362 178.6 (3)

C371—C341—C351—C361 −179.7 (3) C342—C352—C362—C312 −0.4 (4)

C341—C351—C361—C311 −0.3 (5) C322—C312—C362—C352 1.8 (4)

C321—C311—C361—C351 1.6 (4) C32—C312—C362—C352 −178.2 (2)

C31—C311—C361—C351 −177.1 (3) N22—C32—C3A2—C7A2 0.8 (3)

N21—N11—C7A1—N71 −176.9 (2) C312—C32—C3A2—C7A2 −176.5 (3) N21—N11—C7A1—C3A1 0.8 (3) N22—C32—C3A2—C42 178.4 (3)

C3A1—C41—C411—C421 −49.6 (4) C312—C32—C3A2—C42 1.1 (6)

C51—C41—C411—C421 72.9 (3) C32—C3A2—C42—C412 −52.7 (4)

C3A1—C41—C411—C461 130.0 (3) C7A2—C3A2—C42—C412 124.5 (3)

C51—C41—C411—C461 −107.5 (3) C32—C3A2—C42—C52 −175.6 (3)

C461—C411—C421—C431 0.0 (4) C7A2—C3A2—C42—C52 1.7 (4)

C41—C411—C421—C431 179.6 (3) C3A2—C42—C412—C422 −44.2 (3)

C411—C421—C431—C441 −0.5 (5) C52—C42—C412—C422 77.1 (3)

C421—C431—C441—C451 0.3 (5) C3A2—C42—C412—C462 136.4 (3)

C421—C431—C441—Cl41 −178.4 (2) C52—C42—C412—C462 −102.3 (3)

C431—C441—C451—C461 0.3 (5) C462—C412—C422—C432 −0.2 (4)

Cl41—C441—C451—C461 179.0 (2) C42—C412—C422—C432 −179.6 (3)

C421—C411—C461—C451 0.6 (5) C412—C422—C432—C442 −0.2 (5)

C41—C411—C461—C451 −179.0 (3) C422—C432—C442—C452 0.4 (5)

C441—C451—C461—C411 −0.8 (5) C422—C432—C442—Cl42 −179.5 (2)

C3A1—C41—C51—C61 −1.7 (4) C432—C442—C452—C462 −0.3 (5)

C411—C41—C51—C61 −127.2 (3) Cl42—C442—C452—C462 179.6 (2)

C3A1—C41—C51—C511 −179.5 (2) C422—C412—C462—C452 0.3 (4)

C411—C41—C51—C511 55.0 (3) C42—C412—C462—C452 179.7 (3)

C61—C51—C511—N521 −176 (4) C442—C452—C462—C412 −0.1 (4)

C41—C51—C511—N521 2(4) C3A2—C42—C52—C62 −0.4 (4)

C511—C51—C61—N71 173.9 (2) C412—C42—C52—C62 −123.9 (3)

C41—C51—C61—N71 −3.7 (5) C3A2—C42—C52—C512 −178.0 (2)C511—C51—C61—C611 −6.9 (5) C412—C42—C52—C512 58.5 (3)

C41—C51—C61—C611 175.5 (3) C62—C52—C512—N522 177 (4)

C51—C61—C611—C621 −44.1 (4) C42—C52—C512—N522 −5(4)

N71—C61—C611—C621 135.2 (3) C512—C52—C62—N72 175.9 (3)

C51—C61—C611—C661 140.6 (3) C42—C52—C62—N72 −1.5 (4)

N71—C61—C611—C661 −40.1 (4) C512—C52—C62—C612 −1.8 (4)

C661—C611—C621—C631 −0.6 (4) C42—C52—C62—C612 −179.2 (3)

C61—C611—C621—C631 −176.0 (3) C52—C62—C612—C622 −42.1 (4)




sup-9

C611—C621—C631—C641 0.9 (5) N72—C62—C612—C622 140.1 (3)

C621—C631—C641—C651 −0.1 (5) C52—C62—C612—C662 138.7 (3)

C631—C641—C651—C661 −0.9 (5) N72—C62—C612—C662 −39.2 (4)

C641—C651—C661—C611 1.2 (5) C662—C612—C622—C632 −1.6 (4)

C621—C611—C661—C651 −0.4 (4) C62—C612—C622—C632 179.2 (3)

C61—C611—C661—C651 175.0 (3) C612—C622—C632—C642 1.5 (5)

N11—C7A1—C3A1—C31 −0.6 (3) C622—C632—C642—C652 −0.4 (5)

N71—C7A1—C3A1—C31 177.1 (3) C632—C642—C652—C662 −0.6 (5)

N11—C7A1—C3A1—C41 179.5 (2) C642—C652—C662—C612 0.5 (5)

N71—C7A1—C3A1—C41 −2.8 (4) C622—C612—C662—C652 0.6 (4)

N21—C31—C3A1—C7A1 0.2 (3) C62—C612—C662—C652 179.8 (3)

C311—C31—C3A1—C7A1 −177.9 (3) C52—C62—N72—C7A2 2.3 (4)

N21—C31—C3A1—C41 180.0 (3) C612—C62—N72—C7A2 −179.8 (2)

C311—C31—C3A1—C41 2.0 (6) N22—N12—C7A2—N72 −177.4 (2)

C411—C41—C3A1—C7A1 128.8 (3) N22—N12—C7A2—C3A2 0.1 (3)

C51—C41—C3A1—C7A1 4.8 (4) C62—N72—C7A2—N12 176.2 (3)

C411—C41—C3A1—C31 −51.1 (4) C62—N72—C7A2—C3A2 −1.1 (4)

C51—C41—C3A1—C31 −175.0 (3) C32—C3A2—C7A2—N12 −0.6 (3)C51—C61—N71—C7A1 6.2 (4) C42—C3A2—C7A2—N12 −178.5 (3)

C611—C61—N71—C7A1 −173.1 (2) C32—C3A2—C7A2—N72 176.9 (3)

N11—C7A1—N71—C61 174.4 (3) C42—C3A2—C7A2—N72 −1.0 (4)

C3A1—C7A1—N71—C61 −3.1 (4) O1—C1—N2—C3 −176.2 (4)

C7A2—N12—N22—C32 0.4 (3) O1—C1—N2—C4 0.3 (5)

Hydrogen-bond geometry (Å, °)

D —H··· A D —H H··· A D··· A D —H··· A

N21—H21···N12 0.88 2.05 2.801 (4) 142

N22—H22···O1 0.88 1.92 2.775 (3) 164

N72—H72···N11 0.88 2.07 2.889 (3) 155

5-Cyano-4-(4-methoxyphenyl)-3,6-diphenyl-4,7-dihydro-2H -pyrazolo- [3,4-b]pyridine

Crystal data

C26H20 N4O F 000 = 1696

M r = 404.46 Dx = 1.309 Mg m−3

Monoclinic, C 2/cMo K α radiationλ = 0.71073 Å

a = 15.6264 (3) Å Cell parameters from 3620 reflections

b = 12.4397 (2) Å θ = 1.9–25.0ºc = 21.1296 (4) Å µ = 0.08 mm−1

β = 91.4371 (9)º T = 150.0 (1) K

V = 4106.04 (13) Å3 Block, colourless

Z = 8 0.15 × 0.15 × 0.12 mm




sup-10

Data collection




Monochromator: graphite Rint = 0.072T = 150.0(1) K θmax = 25.0º



h = −18→18

T min = 0.988, T max = 0.990 k = −14→14

48325 measured reflections l = −25→25

Refinement

Refinement on F 2Hydrogen site location: inferred from neighbouringsites

Least-squares matrix: full H-atom parameters constrained

R[ F 2 > 2σ( F 2)] = 0.048w = 1/[σ2( F o

2) + (0.0653 P )2 + 4.5942 P ]


2)/3 ?

wR( F 2) = 0.129 (Δ/σ)max < 0.001

S = 1.06 Δρmax = 0.39 e Å−3


282 parametersExtinction correction: SHELXL,

Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4


Extinction coefficient: 0.0026 (4)

Secondary atom site location: difference Fourier map

Special details


(1998). Nonius BV, Delft, The Netherlands], is a graphical user interface written by Enraf–Nonius which encompasses the following






tems cryostream [Cosier, J. & Glazer, A· M . (1986). J. Appl. Cryst. 19, 105–107].


x y z U iso*/U eq

N1 0.05038 (9) −0.10626 (12) 0.16622 (7) 0.0279 (4)

N2 0.10589 (9) −0.07969 (12) 0.12000 (7) 0.0272 (4)

C3 0.08061 (11) 0.00627 (13) 0.08468 (8) 0.0236 (4)

C3A 0.00281 (11) 0.03923 (13) 0.10912 (8) 0.0225 (4)




sup-11

C4 −0.06074 (11) 0.12643 (13) 0.09207 (8) 0.0228 (4)

C5 −0.13673 (10) 0.11692 (13) 0.13635 (8) 0.0227 (4)

C6 −0.14105 (10) 0.04971 (13) 0.18704 (8) 0.0231 (4)

C7A −0.01115 (11) −0.03307 (14) 0.15827 (8) 0.0241 (4)

N7 −0.08121 (9) −0.02914 (12) 0.19728 (7) 0.0270 (4)

C31 0.13386 (11) 0.04772 (14) 0.03369 (8) 0.0250 (4)

C32 0.21403 (12) 0.00425 (18) 0.02201 (9) 0.0372 (5)

C33 0.26367 (13) 0.0443 (2) −0.02583 (10) 0.0464 (6)

C34 0.23519 (14) 0.1301 (2) −0.06221 (10) 0.0435 (5)

C35 0.15542 (15) 0.17275 (18) −0.05173 (10) 0.0447 (5)

C36 0.10469 (13) 0.13157 (16) −0.00493 (9) 0.0360 (5)

C41 −0.02806 (10) 0.24127 (14) 0.09683 (8) 0.0237 (4)

C42 0.02465 (11) 0.27541 (15) 0.14594 (9) 0.0305 (4)

C43 0.04698 (12) 0.38353 (15) 0.15271 (9) 0.0339 (5)

C44 0.01464 (11) 0.45741 (14) 0.10912 (9) 0.0290 (4)

C45 −0.03834 (12) 0.42462 (15) 0.05997 (9) 0.0319 (4)

C46 −0.05916 (12) 0.31775 (15) 0.05342 (9) 0.0294 (4)

O47 0.03091 (9) 0.56606 (10) 0.11148 (7) 0.0394 (4)C48 0.07374 (15) 0.60698 (18) 0.16637 (12) 0.0491 (6)

C51 −0.20549 (11) 0.18912 (14) 0.12249 (8) 0.0255 (4)

N52 −0.25826 (10) 0.24966 (13) 0.10814 (8) 0.0342 (4)

C61 −0.20774 (11) 0.05716 (13) 0.23547 (8) 0.0246 (4)

C62 −0.22894 (12) 0.15675 (14) 0.26054 (9) 0.0302 (4)

C63 −0.29080 (13) 0.16498 (16) 0.30584 (9) 0.0366 (5)

C64 −0.33126 (12) 0.07385 (16) 0.32766 (9) 0.0351 (5)

C65 −0.30997 (12) −0.02564 (16) 0.30391 (9) 0.0337 (4)

C66 −0.24844 (12) −0.03420 (15) 0.25812 (9) 0.0309 (4)

H2 0.1526 −0.1142 0.1138 0.033*

H4 −0.0817 0.1140 0.0486 0.027*

H7 −0.0869 −0.0752 0.2272 0.032*

H32 0.2345 −0.0525 0.0467 0.045*

H33 0.3165 0.0133 −0.0336 0.056*

H34 0.2695 0.1587 −0.0934 0.052*

H35 0.1355 0.2298 −0.0764 0.054*

H36 0.0504 0.1601 0.0009 0.043*

H42 0.0458 0.2256 0.1752 0.037*

H43 0.0830 0.4057 0.1859 0.041*

H45 −0.0601 0.4747 0.0311 0.038*

H46 −0.0944 0.2960 0.0197 0.035*

H48A 0.0451 0.5827 0.2034 0.074*

H48B 0.0733 0.6841 0.1651 0.074*H48C 0.1318 0.5818 0.1677 0.074*

H62 −0.2012 0.2183 0.2467 0.036*

H63 −0.3053 0.2321 0.3217 0.044*

H64 −0.3727 0.0796 0.3583 0.042*

H65 −0.3370 −0.0870 0.3187 0.040*

H66 −0.2342 −0.1015 0.2424 0.037*




sup-12


U 11 U 22 U 33 U 12 U 13 U 23

N1 0.0238 (8) 0.0259 (8) 0.0342 (8) 0.0063 (6) 0.0051 (6) 0.0033 (6)

N2 0.0216 (7) 0.0255 (8) 0.0347 (8) 0.0076 (6) 0.0056 (6) 0.0012 (6)

C3 0.0217 (8) 0.0216 (8) 0.0274 (9) 0.0027 (7) −0.0003 (7) −0.0030 (7)

C3A 0.0219 (9) 0.0194 (8) 0.0264 (9) 0.0024 (7) 0.0012 (7) −0.0025 (7)

C4 0.0219 (9) 0.0215 (9) 0.0249 (9) 0.0036 (7) 0.0004 (7) −0.0004 (7)

C5 0.0192 (8) 0.0187 (8) 0.0302 (9) 0.0018 (7) 0.0015 (7) −0.0020 (7)

C6 0.0171 (8) 0.0198 (8) 0.0324 (9) 0.0006 (6) 0.0012 (7) −0.0022 (7)

C7A 0.0201 (8) 0.0222 (9) 0.0300 (9) 0.0024 (7) 0.0021 (7) −0.0006 (7)

N7 0.0233 (8) 0.0255 (8) 0.0325 (8) 0.0064 (6) 0.0060 (6) 0.0073 (6)

C31 0.0228 (9) 0.0270 (9) 0.0252 (9) 0.0005 (7) 0.0013 (7) −0.0056 (7)

C32 0.0253 (10) 0.0525 (13) 0.0340 (11) 0.0083 (9) 0.0024 (8) 0.0070 (9)

C33 0.0233 (10) 0.0774 (16) 0.0388 (12) 0.0082 (10) 0.0057 (8) 0.0066 (11)

C34 0.0369 (11) 0.0624 (14) 0.0318 (11) −0.0011 (10) 0.0087 (9) 0.0052 (10)

C35 0.0523 (13) 0.0440 (12) 0.0383 (12) 0.0105 (10) 0.0146 (10) 0.0085 (9)C36 0.0375 (11) 0.0366 (11) 0.0344 (11) 0.0116 (9) 0.0113 (8) 0.0024 (8)

C41 0.0194 (8) 0.0229 (9) 0.0289 (9) 0.0032 (7) 0.0071 (7) 0.0004 (7)

C42 0.0266 (9) 0.0256 (9) 0.0393 (11) 0.0031 (7) −0.0012 (8) 0.0023 (8)

C43 0.0274 (10) 0.0341 (11) 0.0399 (11) −0.0031 (8) −0.0031 (8) −0.0002 (8)

C44 0.0242 (9) 0.0225 (9) 0.0406 (11) 0.0027 (7) 0.0095 (8) 0.0051 (8)

C45 0.0297 (10) 0.0302 (10) 0.0360 (10) 0.0045 (8) 0.0043 (8) 0.0089 (8)

C46 0.0292 (10) 0.0295 (10) 0.0297 (9) 0.0025 (8) 0.0045 (7) 0.0035 (7)

O47 0.0382 (8) 0.0251 (7) 0.0550 (9) −0.0039 (6) 0.0009 (7) 0.0036 (6)

C48 0.0443 (13) 0.0356 (12) 0.0672 (15) −0.0100 (10) −0.0056 (11) −0.0065 (10)

C51 0.0219 (9) 0.0232 (9) 0.0316 (9) −0.0001 (8) 0.0043 (7) 0.0004 (7)

N52 0.0258 (8) 0.0305 (9) 0.0466 (10) 0.0075 (7) 0.0054 (7) 0.0052 (7)

C61 0.0179 (8) 0.0242 (9) 0.0316 (9) 0.0008 (7) 0.0000 (7) 0.0016 (7)

C62 0.0301 (10) 0.0256 (9) 0.0354 (10) −0.0059 (8) 0.0076 (8) −0.0031 (7)

C63 0.0395 (11) 0.0313 (10) 0.0397 (11) −0.0032 (9) 0.0125 (9) −0.0068 (8)

C64 0.0306 (10) 0.0393 (11) 0.0358 (11) −0.0015 (9) 0.0108 (8) 0.0011 (8)

C65 0.0262 (9) 0.0312 (10) 0.0439 (11) −0.0029 (8) 0.0058 (8) 0.0089 (8)

C66 0.0273 (9) 0.0225 (9) 0.0431 (11) 0.0029 (7) 0.0041 (8) 0.0042 (8)


N1—C7A 1.332 (2) C34—C35 1.378 (3)

N1—N2 1.363 (2) C35—C36 1.381 (3)

N2—C3 1.357 (2) C41—C42 1.376 (3)C3—C3A 1.394 (2) C41—C46 1.400 (2)

C3—C31 1.471 (2) C42—C43 1.396 (3)

C3A—C7A 1.395 (2) C43—C44 1.387 (3)

C3A—C4 1.508 (2) C44—C45 1.374 (3)

C4—C41 1.520 (2) C44—O47 1.376 (2)

C4—C5 1.535 (2) C45—C46 1.375 (3)

C5—C6 1.362 (2) O47—C48 1.419 (3)

C5—C51 1.425 (2) C51—N52 1.152 (2)




sup-13

C6—N7 1.369 (2) C61—C62 1.391 (2)

C6—C61 1.482 (2) C61—C66 1.393 (2)

C7A—N7 1.388 (2) C62—C63 1.381 (3)

C31—C32 1.392 (3) C63—C64 1.383 (3)

C31—C36 1.394 (3) C64—C65 1.379 (3)

C32—C33 1.382 (3) C65—C66 1.385 (3)

C33—C34 1.383 (3)

C7A—N1—N2 102.37 (13) C32—C33—C34 120.40 (19)

C3—N2—N1 113.78 (14) C35—C34—C33 119.19 (19)

N2—C3—C3A 105.82 (15) C34—C35—C36 120.7 (2)

N2—C3—C31 121.11 (15) C35—C36—C31 120.77 (18)

C3A—C3—C31 133.05 (16) C42—C41—C46 118.41 (16)

C3—C3A—C7A 103.90 (15) C42—C41—C4 122.29 (15)

C3—C3A—C4 134.26 (16) C46—C41—C4 119.00 (15)

C7A—C3A—C4 121.82 (15) C41—C42—C43 121.21 (17)

C3A—C4—C41 116.23 (14) C44—C43—C42 118.96 (18)

C3A—C4—C5 108.29 (13) C45—C44—O47 115.24 (16)

C41—C4—C5 107.21 (13) C45—C44—C43 120.51 (17)C6—C5—C51 119.77 (16) O47—C44—C43 124.25 (18)

C6—C5—C4 125.54 (15) C44—C45—C46 120.00 (17)

C51—C5—C4 114.65 (14) C45—C46—C41 120.91 (17)

C5—C6—N7 121.14 (16) C44—O47—C48 117.70 (16)

C5—C6—C61 123.67 (15) N52—C51—C5 175.78 (19)

N7—C6—C61 115.17 (15) C62—C61—C66 118.73 (16)

N1—C7A—N7 121.81 (15) C62—C61—C6 119.81 (15)

N1—C7A—C3A 114.13 (15) C66—C61—C6 121.43 (16)

N7—C7A—C3A 124.04 (15) C63—C62—C61 120.50 (17)

C6—N7—C7A 118.52 (14) C62—C63—C64 120.28 (18)

C32—C31—C36 117.99 (17) C65—C64—C63 119.85 (17)

C32—C31—C3 121.45 (16) C64—C65—C66 120.08 (17)

C36—C31—C3 120.55 (16) C65—C66—C61 120.54 (17)

C33—C32—C31 120.91 (19)

C7A—N1—N2—C3 0.10 (19) C32—C33—C34—C35 −2.3 (4)

N1—N2—C3—C3A 0.01 (19) C33—C34—C35—C36 0.9 (4)

N1—N2—C3—C31 178.48 (15) C34—C35—C36—C31 1.5 (3)

N2—C3—C3A—C7A −0.12 (18) C32—C31—C36—C35 −2.4 (3)

C31—C3—C3A—C7A −178.32 (18) C3—C31—C36—C35 178.20 (18)

N2—C3—C3A—C4 −178.34 (17) C3A—C4—C41—C42 −41.0 (2)

C31—C3—C3A—C4 3.5 (3) C5—C4—C41—C42 80.28 (19)

C3—C3A—C4—C41 −61.9 (3) C3A—C4—C41—C46 145.50 (16)

C7A—C3A—C4—C41 120.10 (18) C5—C4—C41—C46 −93.24 (18)C3—C3A—C4—C5 177.38 (18) C46—C41—C42—C43 0.0 (3)

C7A—C3A—C4—C5 −0.6 (2) C4—C41—C42—C43 −173.58 (16)

C3A—C4—C5—C6 7.2 (2) C41—C42—C43—C44 0.4 (3)

C41—C4—C5—C6 −118.95 (18) C42—C43—C44—C45 −0.2 (3)

C3A—C4—C5—C51 −175.22 (14) C42—C43—C44—O47 178.86 (17)

C41—C4—C5—C51 58.64 (18) O47—C44—C45—C46 −179.62 (17)

C51—C5—C6—N7 172.13 (15) C43—C44—C45—C46 −0.5 (3)




sup-14

C4—C5—C6—N7 −10.4 (3) C44—C45—C46—C41 0.9 (3)

C51—C5—C6—C61 −9.5 (3) C42—C41—C46—C45 −0.7 (3)

C4—C5—C6—C61 167.99 (15) C4—C41—C46—C45 173.10 (16)

N2—N1—C7A—N7 −178.54 (15) C45—C44—O47—C48 170.21 (17)

N2—N1—C7A—C3A −0.2 (2) C43—C44—O47—C48 −8.9 (3)

C3—C3A—C7A—N1 0.2 (2) C6—C5—C51—N52 −180 (100)

C4—C3A—C7A—N1 178.70 (15) C4—C5—C51—N52 2(3)

C3—C3A—C7A—N7 178.51 (16) C5—C6—C61—C62 −45.5 (2)

C4—C3A—C7A—N7 −3.0 (3) N7—C6—C61—C62 132.96 (17)

C5—C6—N7—C7A 6.0 (2) C5—C6—C61—C66 136.39 (19)

C61—C6—N7—C7A −172.51 (14) N7—C6—C61—C66 −45.1 (2)

N1—C7A—N7—C6 178.70 (16) C66—C61—C62—C63 −1.7 (3)

C3A—C7A—N7—C6 0.5 (3) C6—C61—C62—C63 −179.83 (17)

N2—C3—C31—C32 −3.5 (3) C61—C62—C63—C64 1.2 (3)

C3A—C3—C31—C32 174.44 (18) C62—C63—C64—C65 −0.2 (3)

N2—C3—C31—C36 175.80 (17) C63—C64—C65—C66 −0.3 (3)

C3A—C3—C31—C36 −6.2 (3) C64—C65—C66—C61 −0.2 (3)

C36—C31—C32—C33 1.0 (3) C62—C61—C66—C65 1.2 (3)C3—C31—C32—C33 −179.66 (19) C6—C61—C66—C65 179.29 (16)

C31—C32—C33—C34 1.4 (3)


D —H··· A D —H H··· A D··· A D —H··· A

N2—H2···N52i 0.88 2.18 3.016 (2) 159

N7—H7···N1ii 0.88 2.33 3.065 (2) 142

Symmetry codes: (i) − x, − y−1, − z; (ii) − x, y, − z+1/2.

3,4-Bis(4-chlorophenyl)-5-cyano-6-phenyl-1H -pyrazolo-[3,4-b]pyridine

Crystal data

C25H14Cl2 N4 F 000 = 904

M r = 441.30 Dx = 1.422 Mg m−3

Monoclinic, P 21/nMo K α radiationλ = 0.71073 Å

a = 6.6222 (5) Å Cell parameters from 4026 reflections

b = 11.0791 (10) Å θ = 2.3–26.3º

c = 28.264 (2) Å µ = 0.34 mm−1

β = 96.248 (5)º T = 150.0 (1) K

V = 2061.3 (3) Å3 Plate, colourless

Z = 4 0.10 × 0.10 × 0.05 mm

Data collection







sup-15

Monochromator: graphite Rint = 0.047

T = 150.0(1) K θmax = 26.3º



h = −8→8

T min = 0.967, T max = 0.983 k = −11→13

15117 measured reflections l = −32→35

Refinement

Refinement on F 2 Secondary atom site location: difference Fourier map

Least-squares matrix: fullHydrogen site location: inferred from neighbouringsites

R[ F 2 > 2σ( F 2)] = 0.058 H-atom parameters constrained

wR( F 2) = 0.115w = 1/[σ2( F o

2) + (0.0409 P )2]


2)/3 ?

S = 0.94 (Δ/σ)max < 0.001

4026 reflections Δρmax = 0.40 e Å−3

280 parameters Δρmin = −0.28 e Å−3


Extinction correction: none

Special details


(1998). Nonius BV, Delft, The Netherlands],is a graphical user interface written by Enraf–Nonius which encompasses the following






tems cryostream [Cosier, J. & Glazer, A· M . (1986). J. Appl. Cryst. 19, 105–107].


x y z U iso*/U eq

N1 0.7963 (4) 0.8827 (2) 0.00787 (8) 0.0323 (7)

N2 0.6437 (4) 0.7991 (2) 0.00473 (8) 0.0327 (7)

C3 0.6680 (4) 0.7354 (3) 0.04475 (10) 0.0273 (8)

C31 0.5247 (4) 0.6366 (3) 0.05163 (9) 0.0281 (8)C32 0.5898 (5) 0.5243 (3) 0.06994 (10) 0.0323 (8)

C33 0.4557 (5) 0.4323 (3) 0.07651 (10) 0.0331 (8)

C34 0.2515 (4) 0.4518 (3) 0.06418 (10) 0.0325 (8)

C35 0.1811 (5) 0.5597 (3) 0.04473 (10) 0.0343 (9)

C36 0.3176 (5) 0.6516 (3) 0.03844 (10) 0.0338 (9)

Cl37 0.07847 (12) 0.33802 (8) 0.07379 (3) 0.0480 (3)

C3A 0.8393 (4) 0.7796 (3) 0.07528 (10) 0.0265 (8)




sup-16

C4 0.9369 (4) 0.7569 (3) 0.12093 (10) 0.0268 (8)

C41 0.8737 (4) 0.6620 (3) 0.15319 (9) 0.0266 (8)

C42 1.0024 (5) 0.5685 (3) 0.16882 (10) 0.0321 (8)

C43 0.9463 (5) 0.4849 (3) 0.20075 (10) 0.0379 (9)

C44 0.7595 (5) 0.4964 (3) 0.21729 (10) 0.0333 (8)

C45 0.6269 (5) 0.5872 (3) 0.20222 (10) 0.0358 (9)

C46 0.6835 (4) 0.6690 (3) 0.16961 (10) 0.0323 (8)

Cl47 0.69224 (14) 0.39483 (9) 0.25995 (3) 0.0548 (3)

C5 1.1026 (4) 0.8316 (3) 0.13556 (10) 0.0284 (8)

C51 1.2083 (4) 0.8132 (3) 0.18297 (11) 0.0307 (8)

N52 1.2858 (4) 0.7952 (3) 0.22033 (9) 0.0406 (8)

C6 1.1679 (4) 0.9257 (3) 0.10631 (10) 0.0293 (8)

C61 1.3380 (4) 1.0070 (3) 0.12345 (10) 0.0290 (8)

C62 1.3350 (5) 1.0704 (3) 0.16597 (11) 0.0406 (9)

C63 1.4895 (6) 1.1480 (3) 0.18125 (12) 0.0499 (10)

C64 1.6519 (5) 1.1627 (3) 0.15519 (13) 0.0478 (10)

C65 1.6572 (5) 1.1021 (3) 0.11275 (13) 0.0463 (10)

C66 1.4992 (4) 1.0244 (3) 0.09686 (11) 0.0356 (9) N7 1.0783 (3) 0.9453 (2) 0.06236 (8) 0.0285 (7)

C7A 0.9174 (4) 0.8738 (3) 0.04926 (10) 0.0283 (8)

H1 0.8132 0.9347 −0.0139 0.039*

H32 0.7281 0.5112 0.0779 0.039*

H33 0.5023 0.3586 0.0890 0.040*

H35 0.0430 0.5709 0.0359 0.041*

H36 0.2700 0.7244 0.0252 0.041*

H42 1.1287 0.5622 0.1575 0.039*

H43 1.0328 0.4217 0.2110 0.045*

H45 0.5013 0.5932 0.2139 0.043*

H46 0.5938 0.7297 0.1584 0.039*

H62 1.2273 1.0599 0.1841 0.049*

H63 1.4847 1.1911 0.2094 0.060*

H64 1.7583 1.2136 0.1663 0.057*

H65 1.7656 1.1132 0.0949 0.056*

H66 1.5019 0.9838 0.0681 0.043*


U 11 U 22 U 33 U 12 U 13 U 23

N1 0.0365 (15) 0.0319 (19) 0.0278 (14) −0.0078 (15) 0.0002 (12) 0.0057 (13)

N2 0.0305 (15) 0.038 (2) 0.0293 (15) −0.0045 (15) 0.0037 (12) 0.0015 (14)

C3 0.0307 (19) 0.027 (2) 0.0242 (17) 0.0039 (17) 0.0028 (15) 0.0007 (16)C31 0.0309 (19) 0.032 (2) 0.0216 (16) −0.0011 (18) 0.0024 (14) −0.0048 (15)

C32 0.0289 (18) 0.035 (2) 0.0318 (18) 0.0036 (19) 0.0001 (15) −0.0043 (17)

C33 0.041 (2) 0.026 (2) 0.0327 (18) −0.0051 (19) 0.0052 (16) −0.0001 (16)

C34 0.031 (2) 0.036 (2) 0.0316 (18) −0.0040 (19) 0.0064 (15) −0.0078 (17)

C35 0.0250 (18) 0.038 (3) 0.0397 (19) −0.003 (2) 0.0038 (15) −0.0048 (18)

C36 0.035 (2) 0.034 (2) 0.0306 (18) 0.0014 (19) −0.0021 (16) −0.0002 (16)

Cl37 0.0422 (5) 0.0413 (6) 0.0623 (6) −0.0102 (5) 0.0139 (4) −0.0024 (5)




sup-17

C3A 0.0265 (18) 0.026 (2) 0.0262 (18) 0.0005 (16) 0.0017 (15) 0.0018 (16)

C4 0.0253 (18) 0.029 (2) 0.0262 (17) 0.0028 (17) 0.0060 (14) 0.0011 (16)

C41 0.0270 (18) 0.031 (2) 0.0206 (16) −0.0011 (18) −0.0027 (14) −0.0023 (16)

C42 0.0294 (18) 0.039 (2) 0.0275 (17) 0.0006 (18) −0.0015 (15) 0.0000 (17)

C43 0.047 (2) 0.036 (2) 0.0296 (18) 0.0054 (19) −0.0025 (17) 0.0041 (17)

C44 0.043 (2) 0.030 (2) 0.0258 (17) −0.0093 (19) 0.0013 (16) 0.0012 (17)

C45 0.0338 (19) 0.042 (3) 0.0324 (18) −0.0055 (19) 0.0090 (16) −0.0031 (18)

C46 0.0311 (19) 0.037 (2) 0.0280 (17) 0.0007 (18) 0.0016 (15) 0.0014 (17)

Cl47 0.0667 (6) 0.0549 (7) 0.0431 (5) −0.0167 (5) 0.0067 (5) 0.0140 (5)

C5 0.0261 (18) 0.033 (2) 0.0254 (17) 0.0012 (18) 0.0009 (14) −0.0005 (16)

C51 0.0301 (19) 0.030 (2) 0.033 (2) −0.0034 (17) 0.0068 (16) −0.0023 (17)

N52 0.0408 (17) 0.047 (2) 0.0319 (16) −0.0072 (15) −0.0040 (14) −0.0005 (15)

C6 0.0278 (18) 0.031 (2) 0.0295 (18) 0.0036 (17) 0.0033 (15) −0.0076 (16)

C61 0.0280 (18) 0.030 (2) 0.0281 (18) −0.0007 (17) −0.0025 (15) 0.0032 (16)

C62 0.046 (2) 0.040 (3) 0.0341 (19) −0.007 (2) −0.0018 (17) −0.0023 (18)

C63 0.062 (2) 0.047 (3) 0.038 (2) −0.006 (2) −0.007 (2) −0.0036 (19)

C64 0.048 (2) 0.035 (3) 0.055 (2) −0.010 (2) −0.018 (2) 0.000 (2)

C65 0.031 (2) 0.045 (3) 0.062 (2) −0.005 (2) 0.0023 (18) 0.004 (2)C66 0.0320 (19) 0.035 (2) 0.0395 (19) 0.0020 (19) 0.0003 (16) 0.0003 (17)

N7 0.0288 (15) 0.0336 (18) 0.0226 (14) −0.0019 (15) 0.0007 (12) −0.0021 (13)

C7A 0.0272 (18) 0.036 (2) 0.0216 (17) 0.0075 (18) 0.0019 (15) −0.0023 (16)


N1—C7A 1.348 (3) C42—C43 1.372 (4)

N1—N2 1.367 (3) C43—C44 1.375 (4)

N2—C3 1.328 (3) C44—C45 1.372 (4)

C3—C3A 1.435 (4) C44—Cl47 1.742 (3)

C3—C31 1.475 (4) C45—C46 1.373 (4)

C31—C36 1.392 (4) C5—C6 1.427 (4)C31—C32 1.398 (4) C5—C51 1.457 (4)

C32—C33 1.377 (4) C51—N52 1.140 (3)

C33—C34 1.377 (4) C6—N7 1.335 (3)

C34—C35 1.376 (4) C6—C61 1.482 (4)

C34—Cl37 1.744 (3) C61—C66 1.384 (4)

C35—C36 1.385 (4) C61—C62 1.394 (4)

C3A—C4 1.401 (4) C62—C63 1.370 (4)

C3A—C7A 1.407 (4) C63—C64 1.378 (4)

C4—C5 1.400 (4) C64—C65 1.378 (4)

C4—C41 1.482 (4) C65—C66 1.392 (4)

C41—C42 1.383 (4) N7—C7A 1.347 (4)

C41—C46 1.391 (4)

C7A—N1—N2 111.9 (2) C42—C43—C44 118.6 (3)

C3—N2—N1 106.5 (2) C45—C44—C43 122.1 (3)

N2—C3—C3A 110.2 (3) C45—C44—Cl47 119.0 (2)

N2—C3—C31 119.1 (3) C43—C44—Cl47 118.9 (3)

C3A—C3—C31 130.7 (3) C44—C45—C46 118.7 (3)

C36—C31—C32 117.4 (3) C45—C46—C41 120.7 (3)

C36—C31—C3 120.4 (3) C4—C5—C6 122.5 (3)




C41—C42—C43—C44 −0.5 (4) C4—C3A—C7A—N7 1.1 (5)

C42—C43—C44—C45 1.2 (5) C3—C3A—C7A—N7 179.6 (3)

C42—C43—C44—Cl47 −177.0 (2) C4—C3A—C7A—N1 −177.4 (2)

C43—C44—C45—C46 −0.1 (5) C3—C3A—C7A—N1 1.1 (3)

Cl47—C44—C45—C46 178.1 (2)


D —H··· A D —H H··· A D··· A D —H··· A

N1—H1···N7i 0.88 2.07 2.935 (3) 167

Symmetry codes: (i) − x+2, − y+2, − z.

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