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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1734.
Published online 2010 June 23. doi:  10.1107/S1600536810023317
PMCID: PMC3006872

(7E)-5-Benzyl-7-(2-chloro­benzyl­idene)-3-(2-chloro­phen­yl)-2-phenyl-3,3a,4,5,6,7-hexa­hydro-2H-pyrazolo­[4,3-c]pyridine

Abstract

In the title 2H-pyrazolo­[4,3-c]pyridine derivative, C32H27Cl2N3, the dihydro­pyrazole ring adopts an envelope conformation and the piperidine fused ring a twisted-chair conformation. Two short intra­molecular C—H(...)Cl contacts are observed. The crystal packing is characterized by dimeric C—Cl(...)π inter­actions involving the 5-benzyl ring, with Cl(...)centroid and closest atomic Cl(...)π distances of 3.778 (2) and 3.366 (4) Å, respectively.

Related literature

For the anti-inflammatory activity of 2H-pyrazolo­[4,3-c]pyridine derivatives, see Krapcho & Turk (1975 [triangle]). For π-halogen-dimer inter­actions and their role in host–guest chemistry, see: Noman et al. (2004 [triangle]); Nagaraj et al. (2005 [triangle]).

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Object name is e-66-o1734-scheme1.jpg

Experimental

Crystal data

  • C32H27Cl2N3
  • M r = 524.47
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1734-efi1.jpg
  • a = 13.7117 (7) Å
  • b = 15.4451 (6) Å
  • c = 13.6896 (9) Å
  • β = 113.135 (7)°
  • V = 2666.0 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.27 mm−1
  • T = 294 K
  • 0.36 × 0.26 × 0.22 mm

Data collection

  • Oxford Diffraction Xcalibur Eos Gemini diffractometer
  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 [triangle]) T min = 0.909, T max = 0.943
  • 11774 measured reflections
  • 5436 independent reflections
  • 2483 reflections with I > 2σ(I)
  • R int = 0.049

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.098
  • S = 0.83
  • 5436 reflections
  • 334 parameters
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 [triangle]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97 and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023317/ng2791sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023317/ng2791Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The Bioinformatics Infrastructure Facility and the Single Crystal X-ray Diffractometer Facility at the University of Hyderabad are gratefully acknowledged are gratefully acknowledged for computation and data collection. RSR thanks the CSIR, New Delhi, for support under the scientist’s pool scheme and NSK thanks the CSIR, New Delhi, for a Senior Research Fellowship.

supplementary crystallographic information

Comment

Derivatives of 2H-pyrazolo[4,3-c]pyridine have been tested for anti-inflammatory activity (Krapcho & Turk, 1975). A search in Cambridge Structural Database (version 5.31) for such compounds retrieved zero hits. With a purpose to study hitherto unexplored structures of these compounds, we here report the synthesis and structural investigations on, 5-benzyl-(7E)-7-(2-chlorobenzylidene)-3-(2-chlorophenyl)-2-phenyl- 3,3a,4,5,6,7-hexahydro-2H-pyrazolo[4,3-c]pyridine, (I).

The structure of (I) with adopted atomic numbering scheme is shown in Fig 1. (I) is a racemic mixture. In the reported model, the stereogenic centers C3 and C3A possess R-configurations. The five-membered dihydropyrazole ring (N1/N2/C3/C3A/C7A) adopt an envelope conformation with atom C3 at the flap of the envelope (Ring puckering parameters are: q2 = 0.204 (2) Å, [var phi]2 = 248.3 (6)°). The adjacent 6-membered piperidine ring (C3A/C4/N5/C6/C7/C7A) assumes a chair conformation which is substantially twisted from ideal geometry. The puckering parameters are as follows: q2 = 0.189 (2) Å, q3 = -0.468 (2) Å, θ = 158.0 (2)°, [var phi] = 209.5 (8)°, and total puckering amplitude, Q = 0.505 (2) Å.

Two short intra-molecular contacts C3—H3···Cl1 and C27—H27···Cl2 were observed (Table 1). Intermolecular C—Halogen···π contact stabilizes the dimeric units in (I) (Fig 2). A dimer is formed by C29—Cl2···Cg5i [symmetry code (i): 1 - x, 1 - y, 1 - z]. The Cl2..Cg5 distance and C29—Cl2···Cg5 angle are 3.778 (2)Å and 141.2 (1)° respectively, whereas the minimum atomic distance in Cl2···π is 3.366 (4) Å. Cg5 is the centroid of (C21–C26) ring. The C—Halogen···π dimeric interactions [also referred as PHD; π-halogen-dimer interactions (Noman et al. 2004)] have been shown recently, to play an important role in host–guest chemistry (Nagaraj et al., 2005; references therein).

Experimental

1-benzyl-3, 5-dibenzylidenepiperidin-4-one (0.003 mol) and phenyl hydrazine (0.003 mol) were dissolved in 2-propanol. The reaction mixture was refluxed for 1–2 h on a water bath and tested with TLC at regular intervals for completeness of reaction. Following that, the resulting mixture was cooled and poured into crushed ice. The solid so obtained was separated, washed with water and subjected to column chromatography using ethyl acetate and n-hexane. Final yield 89%, m.p. 153–155° C. Suitable single crystals for data collection were grown from ethanol and tetrahydrofuran mixture in 1:1 ratio.

Refinement

H atoms were placed in their stereochemically expected positions and refined with the riding options. The distances with hydrogen atoms are: C(aromatic/sp2)—H = 0.93 Å, C(methylene)—H = 0.97 Å, C(methine)—H = 0.98 Å, and Uiso = 1.2 Ueq(parent atom).

Figures

Fig. 1.
A view of (I) with non-H atoms shown as probability ellipsoids at 30% levels (Farrugia, 1997). The radii of H atoms are on an arbitrary scale. Dashed lines indicate short intra-molecular C—H···Cl contacts.
Fig. 2.
Dimeric subunits linked by C—Halogen···π interaction in (I). Cg5 is the centroid of (C21—C26) ring.

Crystal data

C32H27Cl2N3F(000) = 1096
Mr = 524.47Dx = 1.307 Mg m3
Monoclinic, P21/cMelting point: 427(2) K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 13.7117 (7) ÅCell parameters from 2998 reflections
b = 15.4451 (6) Åθ = 2.6–29.1°
c = 13.6896 (9) ŵ = 0.27 mm1
β = 113.135 (7)°T = 294 K
V = 2666.0 (2) Å3Plate, colorless
Z = 40.36 × 0.26 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer5436 independent reflections
Radiation source: Enhance (Mo) X-ray Source2483 reflections with I > 2σ(I)
graphiteRint = 0.049
Detector resolution: 16.3291 pixels mm-1θmax = 26.4°, θmin = 2.6°
ω scanh = −14→17
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)k = −19→17
Tmin = 0.909, Tmax = 0.943l = −15→17
11774 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 0.83w = 1/[σ2(Fo2) + (0.0389P)2] where P = (Fo2 + 2Fc2)/3
5436 reflections(Δ/σ)max < 0.001
334 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = −0.23 e Å3

Special details

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05–01-2010 CrysAlis171. NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

xyzUiso*/Ueq
C30.68994 (17)0.48100 (13)0.39914 (17)0.0384 (6)
H30.73430.43160.39790.046*
C3A0.60177 (16)0.44975 (13)0.43353 (18)0.0372 (6)
H3A0.58470.49580.47350.045*
C40.62227 (17)0.36610 (14)0.49646 (19)0.0466 (7)
H4A0.64890.32250.46230.056*
H4B0.67530.37560.56750.056*
C60.44171 (18)0.31461 (13)0.39584 (19)0.0483 (7)
H6A0.37700.29700.40310.058*
H6B0.46650.26590.36710.058*
C70.41706 (18)0.38915 (13)0.31845 (19)0.0399 (6)
C7A0.51168 (17)0.43857 (14)0.32849 (19)0.0396 (6)
C80.67598 (17)0.52120 (13)0.21565 (19)0.0372 (6)
C90.78552 (18)0.51570 (14)0.24683 (19)0.0440 (6)
H90.82860.50280.31700.053*
C100.8300 (2)0.52943 (15)0.1736 (2)0.0538 (7)
H100.90330.52610.19540.065*
C110.7685 (2)0.54792 (15)0.0691 (2)0.0565 (7)
H110.79920.55610.02020.068*
C120.6598 (2)0.55403 (15)0.0385 (2)0.0563 (7)
H120.61730.5671−0.03170.068*
C130.61374 (19)0.54113 (14)0.1102 (2)0.0491 (7)
H130.54060.54580.08820.059*
C140.75983 (17)0.55254 (13)0.46627 (18)0.0371 (6)
C150.86179 (18)0.53885 (15)0.54037 (19)0.0496 (7)
C160.9251 (2)0.60585 (19)0.5984 (2)0.0626 (8)
H160.99350.59460.64740.075*
C170.8869 (2)0.68811 (19)0.5834 (2)0.0629 (8)
H170.92970.73360.62110.075*
C180.7853 (2)0.70400 (16)0.5126 (2)0.0603 (8)
H180.75840.76010.50380.072*
C190.72281 (19)0.63714 (15)0.4546 (2)0.0494 (7)
H190.65420.64890.40640.059*
C200.5425 (2)0.25732 (14)0.5690 (2)0.0565 (7)
H20A0.57100.21250.53810.068*
H20B0.47570.23660.56880.068*
C210.6183 (2)0.27240 (15)0.6818 (2)0.0503 (7)
C220.7124 (2)0.22752 (18)0.7258 (3)0.0785 (10)
H220.72950.18630.68550.094*
C230.7823 (3)0.2434 (2)0.8303 (4)0.0997 (14)
H230.84600.21320.85940.120*
C240.7569 (3)0.3035 (2)0.8899 (3)0.0999 (14)
H240.80350.31410.95960.120*
C250.6636 (3)0.34798 (18)0.8477 (2)0.0777 (9)
H250.64620.38860.88840.093*
C260.5955 (2)0.33212 (16)0.7442 (2)0.0601 (8)
H260.53220.36280.71560.072*
C270.32178 (17)0.41049 (14)0.2455 (2)0.0456 (6)
H270.32000.46180.20920.055*
C280.21940 (17)0.36564 (15)0.21350 (18)0.0413 (6)
C290.12329 (18)0.41044 (14)0.1697 (2)0.0454 (6)
C300.02629 (18)0.36958 (16)0.1313 (2)0.0552 (7)
H30−0.03590.40170.10190.066*
C310.0221 (2)0.28080 (17)0.1368 (2)0.0593 (8)
H31−0.04290.25240.11130.071*
C320.1142 (2)0.23457 (15)0.1800 (2)0.0570 (8)
H320.11150.17460.18450.068*
C330.21102 (19)0.27578 (15)0.21688 (19)0.0507 (7)
H330.27260.24280.24480.061*
N10.52729 (14)0.47054 (11)0.24903 (16)0.0431 (5)
N20.62818 (14)0.51001 (11)0.28892 (15)0.0403 (5)
N50.52271 (14)0.33591 (11)0.50228 (15)0.0428 (5)
Cl10.91528 (6)0.43491 (4)0.56217 (7)0.0870 (3)
Cl20.12374 (5)0.52302 (4)0.16351 (7)0.0764 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C30.0318 (12)0.0456 (13)0.0375 (14)0.0018 (11)0.0133 (12)0.0007 (12)
C3A0.0334 (13)0.0410 (14)0.0401 (14)−0.0001 (10)0.0174 (12)−0.0006 (12)
C40.0388 (14)0.0504 (15)0.0494 (16)−0.0005 (11)0.0161 (14)0.0036 (13)
C60.0433 (15)0.0498 (15)0.0512 (17)−0.0036 (12)0.0179 (14)−0.0057 (13)
C70.0361 (14)0.0483 (14)0.0384 (15)−0.0021 (11)0.0179 (13)−0.0016 (12)
C7A0.0332 (14)0.0460 (14)0.0429 (16)0.0006 (11)0.0187 (13)0.0023 (12)
C80.0335 (14)0.0410 (13)0.0380 (14)−0.0044 (11)0.0152 (13)−0.0030 (12)
C90.0394 (15)0.0571 (15)0.0380 (15)0.0010 (12)0.0180 (13)−0.0014 (12)
C100.0424 (15)0.0719 (17)0.0555 (18)−0.0033 (13)0.0281 (16)−0.0068 (15)
C110.0635 (19)0.0644 (17)0.0556 (19)−0.0102 (14)0.0384 (17)−0.0052 (15)
C120.0599 (19)0.0697 (17)0.0403 (16)−0.0072 (14)0.0208 (16)0.0048 (14)
C130.0379 (14)0.0639 (17)0.0440 (16)−0.0046 (12)0.0143 (14)0.0015 (14)
C140.0351 (13)0.0438 (14)0.0352 (14)−0.0031 (11)0.0167 (12)−0.0005 (12)
C150.0405 (14)0.0607 (16)0.0414 (15)−0.0023 (13)0.0095 (14)−0.0021 (13)
C160.0460 (16)0.084 (2)0.0463 (18)−0.0079 (16)0.0063 (15)−0.0097 (16)
C170.063 (2)0.074 (2)0.0553 (19)−0.0245 (16)0.0269 (17)−0.0207 (16)
C180.070 (2)0.0479 (15)0.072 (2)−0.0065 (14)0.0376 (19)−0.0086 (15)
C190.0418 (15)0.0516 (16)0.0548 (17)0.0009 (13)0.0187 (14)−0.0034 (14)
C200.0609 (17)0.0449 (15)0.0643 (19)−0.0002 (13)0.0252 (17)0.0074 (14)
C210.0457 (16)0.0430 (15)0.0597 (19)0.0010 (13)0.0179 (16)0.0206 (15)
C220.063 (2)0.0688 (19)0.102 (3)0.0148 (16)0.031 (2)0.037 (2)
C230.051 (2)0.090 (3)0.130 (4)0.010 (2)0.007 (3)0.064 (3)
C240.073 (3)0.095 (3)0.090 (3)−0.032 (2)−0.013 (2)0.049 (2)
C250.083 (2)0.077 (2)0.057 (2)−0.0231 (18)0.010 (2)0.0085 (18)
C260.0543 (18)0.0576 (17)0.0574 (19)−0.0043 (14)0.0100 (17)0.0125 (16)
C270.0397 (15)0.0499 (14)0.0486 (17)−0.0030 (12)0.0189 (14)0.0001 (13)
C280.0369 (14)0.0516 (15)0.0361 (15)−0.0030 (12)0.0152 (13)−0.0033 (12)
C290.0399 (15)0.0487 (14)0.0493 (16)−0.0047 (12)0.0193 (14)0.0013 (13)
C300.0377 (15)0.0598 (17)0.0600 (19)0.0001 (12)0.0104 (15)0.0037 (15)
C310.0448 (16)0.0624 (18)0.0586 (19)−0.0144 (14)0.0072 (16)−0.0048 (15)
C320.0527 (17)0.0477 (15)0.0564 (18)−0.0077 (13)0.0060 (16)−0.0058 (14)
C330.0448 (16)0.0528 (16)0.0465 (16)−0.0005 (12)0.0093 (14)−0.0077 (13)
N10.0299 (11)0.0542 (12)0.0451 (13)−0.0051 (9)0.0145 (11)−0.0001 (11)
N20.0287 (11)0.0570 (12)0.0350 (12)−0.0049 (9)0.0124 (10)0.0001 (10)
N50.0400 (12)0.0443 (11)0.0434 (12)−0.0051 (9)0.0156 (11)0.0044 (10)
Cl10.0653 (5)0.0766 (5)0.0839 (6)0.0217 (4)−0.0087 (5)0.0038 (4)
Cl20.0549 (4)0.0535 (4)0.1194 (7)0.0007 (3)0.0327 (5)0.0127 (4)

Geometric parameters (Å, °)

C3—N21.480 (3)C17—C181.372 (3)
C3—C141.514 (3)C17—H170.9300
C3—C3A1.537 (3)C18—C191.377 (3)
C3—H30.9800C18—H180.9300
C3A—C7A1.493 (3)C19—H190.9300
C3A—C41.517 (3)C20—N51.478 (3)
C3A—H3A0.9800C20—C211.503 (3)
C4—N51.474 (3)C20—H20A0.9700
C4—H4A0.9700C20—H20B0.9700
C4—H4B0.9700C21—C261.373 (3)
C6—N51.481 (3)C21—C221.377 (3)
C6—C71.510 (3)C22—C231.397 (4)
C6—H6A0.9700C22—H220.9300
C6—H6B0.9700C23—C241.368 (5)
C7—C271.337 (3)C23—H230.9300
C7—C7A1.464 (3)C24—C251.364 (4)
C7A—N11.287 (3)C24—H240.9300
C8—C131.392 (3)C25—C261.379 (3)
C8—C91.393 (3)C25—H250.9300
C8—N21.408 (3)C26—H260.9300
C9—C101.379 (3)C27—C281.470 (3)
C9—H90.9300C27—H270.9300
C10—C111.375 (3)C28—C331.395 (3)
C10—H100.9300C28—C291.398 (3)
C11—C121.383 (3)C29—C301.376 (3)
C11—H110.9300C29—Cl21.741 (2)
C12—C131.375 (3)C30—C311.376 (3)
C12—H120.9300C30—H300.9300
C13—H130.9300C31—C321.367 (3)
C14—C151.383 (3)C31—H310.9300
C14—C191.388 (3)C32—C331.376 (3)
C15—C161.383 (3)C32—H320.9300
C15—Cl11.741 (2)C33—H330.9300
C16—C171.359 (3)N1—N21.411 (2)
C16—H160.9300
N2—C3—C14111.73 (17)C18—C17—H17120.1
N2—C3—C3A101.74 (17)C17—C18—C19120.2 (2)
C14—C3—C3A115.45 (19)C17—C18—H18119.9
N2—C3—H3109.2C19—C18—H18119.9
C14—C3—H3109.2C18—C19—C14121.5 (2)
C3A—C3—H3109.2C18—C19—H19119.2
C7A—C3A—C4110.32 (17)C14—C19—H19119.2
C7A—C3A—C3101.19 (18)N5—C20—C21113.11 (18)
C4—C3A—C3116.68 (18)N5—C20—H20A109.0
C7A—C3A—H3A109.4C21—C20—H20A109.0
C4—C3A—H3A109.4N5—C20—H20B109.0
C3—C3A—H3A109.4C21—C20—H20B109.0
N5—C4—C3A109.35 (17)H20A—C20—H20B107.8
N5—C4—H4A109.8C26—C21—C22118.0 (3)
C3A—C4—H4A109.8C26—C21—C20120.6 (2)
N5—C4—H4B109.8C22—C21—C20121.5 (3)
C3A—C4—H4B109.8C21—C22—C23120.5 (3)
H4A—C4—H4B108.3C21—C22—H22119.8
N5—C6—C7113.30 (17)C23—C22—H22119.8
N5—C6—H6A108.9C24—C23—C22119.8 (3)
C7—C6—H6A108.9C24—C23—H23120.1
N5—C6—H6B108.9C22—C23—H23120.1
C7—C6—H6B108.9C25—C24—C23120.3 (3)
H6A—C6—H6B107.7C25—C24—H24119.8
C27—C7—C7A120.7 (2)C23—C24—H24119.8
C27—C7—C6126.6 (2)C24—C25—C26119.3 (3)
C7A—C7—C6112.69 (19)C24—C25—H25120.4
N1—C7A—C7123.8 (2)C26—C25—H25120.4
N1—C7A—C3A114.9 (2)C21—C26—C25122.1 (3)
C7—C7A—C3A121.2 (2)C21—C26—H26119.0
C13—C8—C9118.6 (2)C25—C26—H26119.0
C13—C8—N2119.9 (2)C7—C27—C28130.2 (2)
C9—C8—N2121.5 (2)C7—C27—H27114.9
C10—C9—C8120.0 (2)C28—C27—H27114.9
C10—C9—H9120.0C33—C28—C29115.5 (2)
C8—C9—H9120.0C33—C28—C27122.7 (2)
C11—C10—C9121.4 (2)C29—C28—C27121.6 (2)
C11—C10—H10119.3C30—C29—C28122.9 (2)
C9—C10—H10119.3C30—C29—Cl2117.43 (18)
C10—C11—C12118.5 (3)C28—C29—Cl2119.63 (17)
C10—C11—H11120.7C31—C30—C29119.4 (2)
C12—C11—H11120.7C31—C30—H30120.3
C13—C12—C11121.1 (3)C29—C30—H30120.3
C13—C12—H12119.5C32—C31—C30119.6 (2)
C11—C12—H12119.5C32—C31—H31120.2
C12—C13—C8120.4 (2)C30—C31—H31120.2
C12—C13—H13119.8C31—C32—C33120.7 (2)
C8—C13—H13119.8C31—C32—H32119.6
C15—C14—C19116.5 (2)C33—C32—H32119.6
C15—C14—C3123.4 (2)C32—C33—C28121.9 (2)
C19—C14—C3120.10 (19)C32—C33—H33119.1
C16—C15—C14122.2 (2)C28—C33—H33119.1
C16—C15—Cl1117.7 (2)C7A—N1—N2107.59 (19)
C14—C15—Cl1120.18 (18)C8—N2—N1115.95 (18)
C17—C16—C15119.7 (2)C8—N2—C3121.56 (17)
C17—C16—H16120.2N1—N2—C3110.18 (17)
C15—C16—H16120.2C4—N5—C20110.11 (18)
C16—C17—C18119.9 (2)C4—N5—C6111.69 (18)
C16—C17—H17120.1C20—N5—C6108.06 (17)
N2—C3—C3A—C7A18.3 (2)C26—C21—C22—C23−0.6 (4)
C14—C3—C3A—C7A139.43 (18)C20—C21—C22—C23179.1 (2)
N2—C3—C3A—C4137.96 (19)C21—C22—C23—C240.5 (5)
C14—C3—C3A—C4−100.9 (2)C22—C23—C24—C250.0 (5)
C7A—C3A—C4—N5−52.9 (2)C23—C24—C25—C26−0.4 (5)
C3—C3A—C4—N5−167.63 (18)C22—C21—C26—C250.2 (4)
N5—C6—C7—C27−141.8 (2)C20—C21—C26—C25−179.5 (2)
N5—C6—C7—C7A39.4 (3)C24—C25—C26—C210.3 (4)
C27—C7—C7A—N1−36.8 (3)C7A—C7—C27—C28172.6 (2)
C6—C7—C7A—N1142.1 (2)C6—C7—C27—C28−6.1 (4)
C27—C7—C7A—C3A147.8 (2)C7—C27—C28—C33−31.2 (4)
C6—C7—C7A—C3A−33.3 (3)C7—C27—C28—C29153.8 (3)
C4—C3A—C7A—N1−135.4 (2)C33—C28—C29—C30−0.6 (4)
C3—C3A—C7A—N1−11.3 (2)C27—C28—C29—C30174.7 (2)
C4—C3A—C7A—C740.4 (3)C33—C28—C29—Cl2178.85 (18)
C3—C3A—C7A—C7164.53 (19)C27—C28—C29—Cl2−5.9 (3)
C13—C8—C9—C10−0.4 (3)C28—C29—C30—C310.9 (4)
N2—C8—C9—C10−178.2 (2)Cl2—C29—C30—C31−178.6 (2)
C8—C9—C10—C11−0.6 (4)C29—C30—C31—C32−0.2 (4)
C9—C10—C11—C121.1 (4)C30—C31—C32—C33−0.8 (4)
C10—C11—C12—C13−0.6 (4)C31—C32—C33—C281.1 (4)
C11—C12—C13—C8−0.3 (4)C29—C28—C33—C32−0.4 (4)
C9—C8—C13—C120.8 (3)C27—C28—C33—C32−175.6 (2)
N2—C8—C13—C12178.6 (2)C7—C7A—N1—N2−177.40 (19)
N2—C3—C14—C15−140.5 (2)C3A—C7A—N1—N2−1.7 (3)
C3A—C3—C14—C15103.9 (3)C13—C8—N2—N135.8 (3)
N2—C3—C14—C1939.0 (3)C9—C8—N2—N1−146.42 (19)
C3A—C3—C14—C19−76.6 (3)C13—C8—N2—C3174.33 (19)
C19—C14—C15—C16−1.5 (4)C9—C8—N2—C3−7.9 (3)
C3—C14—C15—C16178.0 (2)C7A—N1—N2—C8158.2 (2)
C19—C14—C15—Cl1179.33 (19)C7A—N1—N2—C315.1 (2)
C3—C14—C15—Cl1−1.2 (3)C14—C3—N2—C874.5 (2)
C14—C15—C16—C170.3 (4)C3A—C3—N2—C8−161.78 (18)
Cl1—C15—C16—C17179.5 (2)C14—C3—N2—N1−144.89 (18)
C15—C16—C17—C181.3 (4)C3A—C3—N2—N1−21.2 (2)
C16—C17—C18—C19−1.8 (4)C3A—C4—N5—C20−176.51 (18)
C17—C18—C19—C140.6 (4)C3A—C4—N5—C663.4 (2)
C15—C14—C19—C181.1 (4)C21—C20—N5—C461.7 (3)
C3—C14—C19—C18−178.5 (2)C21—C20—N5—C6−176.1 (2)
N5—C20—C21—C2659.8 (3)C7—C6—N5—C4−56.7 (2)
N5—C20—C21—C22−119.9 (2)C7—C6—N5—C20−178.0 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3···Cl10.982.613.101 (2)111
C27—H27···Cl20.932.683.043 (3)104

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2791).

References

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  • Noman, A., Rehman, M. M., Bishop, R., Craig, D. C. & Scudder, M. L. (2004). J. Org. Biomol. Chem.2, 175–182. [PubMed]
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