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

Karthikeyan, N.S.; Mahesh, B.U.; Sathiyanarayanan, K.; Raghavaiah, P.; Rathore, R.S.

doi:10.1107/S1600536810023317

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1734

doi:10.1107/S1600536810023317

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

N. S. Karthikeyan,^a B. Uma Mahesh,^a K. Sathiyanarayanan,^a P. Raghavaiah ^b and R. S. Rathore ^c ^*

^aChemistry Division, School of Science and Humanities, VIT University, Vellore 632 014, India, ^bSchool of Chemistry, University of Hyderabad, Hyderabad 500 046, India, and ^cBioinformatics Infrastructure Facility, Department of Biotechnology, School of Life Science, University of Hyderabad, Hyderabad 500 046, India
^*Correspondence e-mail: ravindranath_rathore@yahoo.com

(Received 15 June 2010; accepted 16 June 2010; online 23 June 2010)

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 ). For π-halogen-dimer interactions and their role in host–guest chemistry, see: Noman et al. (2004 ); Nagaraj et al. (2005 ).

Experimental

Crystal data

C₃₂H₂₇Cl₂N₃
M_r = 524.47
Monoclinic, P 2₁ /c
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 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.098
S = 0.83
5436 reflections
334 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cl1	0.98	2.61	3.101 (2)	111
C27—H27⋯Cl2	0.93	2.68	3.043 (3)	104

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

Supporting information

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

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

checkCIF report

Comment top

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, ϕ2 = 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)°, ϕ = 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).

Related literature top

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

Experimental top

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.

Computing details top

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

Figures top

	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.

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

Crystal data top

C₃₂H₂₇Cl₂N₃	F(000) = 1096
M_r = 524.47	D_x = 1.307 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 427(2) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.7117 (7) Å	Cell parameters from 2998 reflections
b = 15.4451 (6) Å	θ = 2.6–29.1°
c = 13.6896 (9) Å	µ = 0.27 mm⁻¹
β = 113.135 (7)°	T = 294 K
V = 2666.0 (2) Å³	Plate, colorless
Z = 4	0.36 × 0.26 × 0.22 mm

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	5436 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2483 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
Detector resolution: 16.3291 pixels mm^-1	θ_max = 26.4°, θ_min = 2.6°
ω scan	h = −14→17
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −19→17
T_min = 0.909, T_max = 0.943	l = −15→17
11774 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 0.83	w = 1/[σ²(F_o²) + (0.0389P)²] where P = (F_o² + 2F_c²)/3
5436 reflections	(Δ/σ)_max < 0.001
334 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₃₂H₂₇Cl₂N₃	V = 2666.0 (2) Å³
M_r = 524.47	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.7117 (7) Å	µ = 0.27 mm⁻¹
b = 15.4451 (6) Å	T = 294 K
c = 13.6896 (9) Å	0.36 × 0.26 × 0.22 mm
β = 113.135 (7)°

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	5436 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	2483 reflections with I > 2σ(I)
T_min = 0.909, T_max = 0.943	R_int = 0.049
11774 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 0.83	Δρ_max = 0.17 e Å⁻³
5436 reflections	Δρ_min = −0.23 e Å⁻³
334 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
C3	0.68994 (17)	0.48100 (13)	0.39914 (17)	0.0384 (6)
H3	0.7343	0.4316	0.3979	0.046*
C3A	0.60177 (16)	0.44975 (13)	0.43353 (18)	0.0372 (6)
H3A	0.5847	0.4958	0.4735	0.045*
C4	0.62227 (17)	0.36610 (14)	0.49646 (19)	0.0466 (7)
H4A	0.6489	0.3225	0.4623	0.056*
H4B	0.6753	0.3756	0.5675	0.056*
C6	0.44171 (18)	0.31461 (13)	0.39584 (19)	0.0483 (7)
H6A	0.3770	0.2970	0.4031	0.058*
H6B	0.4665	0.2659	0.3671	0.058*
C7	0.41706 (18)	0.38915 (13)	0.31845 (19)	0.0399 (6)
C7A	0.51168 (17)	0.43857 (14)	0.32849 (19)	0.0396 (6)
C8	0.67598 (17)	0.52120 (13)	0.21565 (19)	0.0372 (6)
C9	0.78552 (18)	0.51570 (14)	0.24683 (19)	0.0440 (6)
H9	0.8286	0.5028	0.3170	0.053*
C10	0.8300 (2)	0.52943 (15)	0.1736 (2)	0.0538 (7)
H10	0.9033	0.5261	0.1954	0.065*
C11	0.7685 (2)	0.54792 (15)	0.0691 (2)	0.0565 (7)
H11	0.7992	0.5561	0.0202	0.068*
C12	0.6598 (2)	0.55403 (15)	0.0385 (2)	0.0563 (7)
H12	0.6173	0.5671	−0.0317	0.068*
C13	0.61374 (19)	0.54113 (14)	0.1102 (2)	0.0491 (7)
H13	0.5406	0.5458	0.0882	0.059*
C14	0.75983 (17)	0.55254 (13)	0.46627 (18)	0.0371 (6)
C15	0.86179 (18)	0.53885 (15)	0.54037 (19)	0.0496 (7)
C16	0.9251 (2)	0.60585 (19)	0.5984 (2)	0.0626 (8)
H16	0.9935	0.5946	0.6474	0.075*
C17	0.8869 (2)	0.68811 (19)	0.5834 (2)	0.0629 (8)
H17	0.9297	0.7336	0.6211	0.075*
C18	0.7853 (2)	0.70400 (16)	0.5126 (2)	0.0603 (8)
H18	0.7584	0.7601	0.5038	0.072*
C19	0.72281 (19)	0.63714 (15)	0.4546 (2)	0.0494 (7)
H19	0.6542	0.6489	0.4064	0.059*
C20	0.5425 (2)	0.25732 (14)	0.5690 (2)	0.0565 (7)
H20A	0.5710	0.2125	0.5381	0.068*
H20B	0.4757	0.2366	0.5688	0.068*
C21	0.6183 (2)	0.27240 (15)	0.6818 (2)	0.0503 (7)
C22	0.7124 (2)	0.22752 (18)	0.7258 (3)	0.0785 (10)
H22	0.7295	0.1863	0.6855	0.094*
C23	0.7823 (3)	0.2434 (2)	0.8303 (4)	0.0997 (14)
H23	0.8460	0.2132	0.8594	0.120*
C24	0.7569 (3)	0.3035 (2)	0.8899 (3)	0.0999 (14)
H24	0.8035	0.3141	0.9596	0.120*
C25	0.6636 (3)	0.34798 (18)	0.8477 (2)	0.0777 (9)
H25	0.6462	0.3886	0.8884	0.093*
C26	0.5955 (2)	0.33212 (16)	0.7442 (2)	0.0601 (8)
H26	0.5322	0.3628	0.7156	0.072*
C27	0.32178 (17)	0.41049 (14)	0.2455 (2)	0.0456 (6)
H27	0.3200	0.4618	0.2092	0.055*
C28	0.21940 (17)	0.36564 (15)	0.21350 (18)	0.0413 (6)
C29	0.12329 (18)	0.41044 (14)	0.1697 (2)	0.0454 (6)
C30	0.02629 (18)	0.36958 (16)	0.1313 (2)	0.0552 (7)
H30	−0.0359	0.4017	0.1019	0.066*
C31	0.0221 (2)	0.28080 (17)	0.1368 (2)	0.0593 (8)
H31	−0.0429	0.2524	0.1113	0.071*
C32	0.1142 (2)	0.23457 (15)	0.1800 (2)	0.0570 (8)
H32	0.1115	0.1746	0.1845	0.068*
C33	0.21102 (19)	0.27578 (15)	0.21688 (19)	0.0507 (7)
H33	0.2726	0.2428	0.2448	0.061*
N1	0.52729 (14)	0.47054 (11)	0.24903 (16)	0.0431 (5)
N2	0.62818 (14)	0.51001 (11)	0.28892 (15)	0.0403 (5)
N5	0.52271 (14)	0.33591 (11)	0.50228 (15)	0.0428 (5)
Cl1	0.91528 (6)	0.43491 (4)	0.56217 (7)	0.0870 (3)
Cl2	0.12374 (5)	0.52302 (4)	0.16351 (7)	0.0764 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C3	0.0318 (12)	0.0456 (13)	0.0375 (14)	0.0018 (11)	0.0133 (12)	0.0007 (12)
C3A	0.0334 (13)	0.0410 (14)	0.0401 (14)	−0.0001 (10)	0.0174 (12)	−0.0006 (12)
C4	0.0388 (14)	0.0504 (15)	0.0494 (16)	−0.0005 (11)	0.0161 (14)	0.0036 (13)
C6	0.0433 (15)	0.0498 (15)	0.0512 (17)	−0.0036 (12)	0.0179 (14)	−0.0057 (13)
C7	0.0361 (14)	0.0483 (14)	0.0384 (15)	−0.0021 (11)	0.0179 (13)	−0.0016 (12)
C7A	0.0332 (14)	0.0460 (14)	0.0429 (16)	0.0006 (11)	0.0187 (13)	0.0023 (12)
C8	0.0335 (14)	0.0410 (13)	0.0380 (14)	−0.0044 (11)	0.0152 (13)	−0.0030 (12)
C9	0.0394 (15)	0.0571 (15)	0.0380 (15)	0.0010 (12)	0.0180 (13)	−0.0014 (12)
C10	0.0424 (15)	0.0719 (17)	0.0555 (18)	−0.0033 (13)	0.0281 (16)	−0.0068 (15)
C11	0.0635 (19)	0.0644 (17)	0.0556 (19)	−0.0102 (14)	0.0384 (17)	−0.0052 (15)
C12	0.0599 (19)	0.0697 (17)	0.0403 (16)	−0.0072 (14)	0.0208 (16)	0.0048 (14)
C13	0.0379 (14)	0.0639 (17)	0.0440 (16)	−0.0046 (12)	0.0143 (14)	0.0015 (14)
C14	0.0351 (13)	0.0438 (14)	0.0352 (14)	−0.0031 (11)	0.0167 (12)	−0.0005 (12)
C15	0.0405 (14)	0.0607 (16)	0.0414 (15)	−0.0023 (13)	0.0095 (14)	−0.0021 (13)
C16	0.0460 (16)	0.084 (2)	0.0463 (18)	−0.0079 (16)	0.0063 (15)	−0.0097 (16)
C17	0.063 (2)	0.074 (2)	0.0553 (19)	−0.0245 (16)	0.0269 (17)	−0.0207 (16)
C18	0.070 (2)	0.0479 (15)	0.072 (2)	−0.0065 (14)	0.0376 (19)	−0.0086 (15)
C19	0.0418 (15)	0.0516 (16)	0.0548 (17)	0.0009 (13)	0.0187 (14)	−0.0034 (14)
C20	0.0609 (17)	0.0449 (15)	0.0643 (19)	−0.0002 (13)	0.0252 (17)	0.0074 (14)
C21	0.0457 (16)	0.0430 (15)	0.0597 (19)	0.0010 (13)	0.0179 (16)	0.0206 (15)
C22	0.063 (2)	0.0688 (19)	0.102 (3)	0.0148 (16)	0.031 (2)	0.037 (2)
C23	0.051 (2)	0.090 (3)	0.130 (4)	0.010 (2)	0.007 (3)	0.064 (3)
C24	0.073 (3)	0.095 (3)	0.090 (3)	−0.032 (2)	−0.013 (2)	0.049 (2)
C25	0.083 (2)	0.077 (2)	0.057 (2)	−0.0231 (18)	0.010 (2)	0.0085 (18)
C26	0.0543 (18)	0.0576 (17)	0.0574 (19)	−0.0043 (14)	0.0100 (17)	0.0125 (16)
C27	0.0397 (15)	0.0499 (14)	0.0486 (17)	−0.0030 (12)	0.0189 (14)	0.0001 (13)
C28	0.0369 (14)	0.0516 (15)	0.0361 (15)	−0.0030 (12)	0.0152 (13)	−0.0033 (12)
C29	0.0399 (15)	0.0487 (14)	0.0493 (16)	−0.0047 (12)	0.0193 (14)	0.0013 (13)
C30	0.0377 (15)	0.0598 (17)	0.0600 (19)	0.0001 (12)	0.0104 (15)	0.0037 (15)
C31	0.0448 (16)	0.0624 (18)	0.0586 (19)	−0.0144 (14)	0.0072 (16)	−0.0048 (15)
C32	0.0527 (17)	0.0477 (15)	0.0564 (18)	−0.0077 (13)	0.0060 (16)	−0.0058 (14)
C33	0.0448 (16)	0.0528 (16)	0.0465 (16)	−0.0005 (12)	0.0093 (14)	−0.0077 (13)
N1	0.0299 (11)	0.0542 (12)	0.0451 (13)	−0.0051 (9)	0.0145 (11)	−0.0001 (11)
N2	0.0287 (11)	0.0570 (12)	0.0350 (12)	−0.0049 (9)	0.0124 (10)	0.0001 (10)
N5	0.0400 (12)	0.0443 (11)	0.0434 (12)	−0.0051 (9)	0.0156 (11)	0.0044 (10)
Cl1	0.0653 (5)	0.0766 (5)	0.0839 (6)	0.0217 (4)	−0.0087 (5)	0.0038 (4)
Cl2	0.0549 (4)	0.0535 (4)	0.1194 (7)	0.0007 (3)	0.0327 (5)	0.0127 (4)

Geometric parameters (Å, º) top

C3—N2	1.480 (3)	C17—C18	1.372 (3)
C3—C14	1.514 (3)	C17—H17	0.9300
C3—C3A	1.537 (3)	C18—C19	1.377 (3)
C3—H3	0.9800	C18—H18	0.9300
C3A—C7A	1.493 (3)	C19—H19	0.9300
C3A—C4	1.517 (3)	C20—N5	1.478 (3)
C3A—H3A	0.9800	C20—C21	1.503 (3)
C4—N5	1.474 (3)	C20—H20A	0.9700
C4—H4A	0.9700	C20—H20B	0.9700
C4—H4B	0.9700	C21—C26	1.373 (3)
C6—N5	1.481 (3)	C21—C22	1.377 (3)
C6—C7	1.510 (3)	C22—C23	1.397 (4)
C6—H6A	0.9700	C22—H22	0.9300
C6—H6B	0.9700	C23—C24	1.368 (5)
C7—C27	1.337 (3)	C23—H23	0.9300
C7—C7A	1.464 (3)	C24—C25	1.364 (4)
C7A—N1	1.287 (3)	C24—H24	0.9300
C8—C13	1.392 (3)	C25—C26	1.379 (3)
C8—C9	1.393 (3)	C25—H25	0.9300
C8—N2	1.408 (3)	C26—H26	0.9300
C9—C10	1.379 (3)	C27—C28	1.470 (3)
C9—H9	0.9300	C27—H27	0.9300
C10—C11	1.375 (3)	C28—C33	1.395 (3)
C10—H10	0.9300	C28—C29	1.398 (3)
C11—C12	1.383 (3)	C29—C30	1.376 (3)
C11—H11	0.9300	C29—Cl2	1.741 (2)
C12—C13	1.375 (3)	C30—C31	1.376 (3)
C12—H12	0.9300	C30—H30	0.9300
C13—H13	0.9300	C31—C32	1.367 (3)
C14—C15	1.383 (3)	C31—H31	0.9300
C14—C19	1.388 (3)	C32—C33	1.376 (3)
C15—C16	1.383 (3)	C32—H32	0.9300
C15—Cl1	1.741 (2)	C33—H33	0.9300
C16—C17	1.359 (3)	N1—N2	1.411 (2)
C16—H16	0.9300

N2—C3—C14	111.73 (17)	C18—C17—H17	120.1
N2—C3—C3A	101.74 (17)	C17—C18—C19	120.2 (2)
C14—C3—C3A	115.45 (19)	C17—C18—H18	119.9
N2—C3—H3	109.2	C19—C18—H18	119.9
C14—C3—H3	109.2	C18—C19—C14	121.5 (2)
C3A—C3—H3	109.2	C18—C19—H19	119.2
C7A—C3A—C4	110.32 (17)	C14—C19—H19	119.2
C7A—C3A—C3	101.19 (18)	N5—C20—C21	113.11 (18)
C4—C3A—C3	116.68 (18)	N5—C20—H20A	109.0
C7A—C3A—H3A	109.4	C21—C20—H20A	109.0
C4—C3A—H3A	109.4	N5—C20—H20B	109.0
C3—C3A—H3A	109.4	C21—C20—H20B	109.0
N5—C4—C3A	109.35 (17)	H20A—C20—H20B	107.8
N5—C4—H4A	109.8	C26—C21—C22	118.0 (3)
C3A—C4—H4A	109.8	C26—C21—C20	120.6 (2)
N5—C4—H4B	109.8	C22—C21—C20	121.5 (3)
C3A—C4—H4B	109.8	C21—C22—C23	120.5 (3)
H4A—C4—H4B	108.3	C21—C22—H22	119.8
N5—C6—C7	113.30 (17)	C23—C22—H22	119.8
N5—C6—H6A	108.9	C24—C23—C22	119.8 (3)
C7—C6—H6A	108.9	C24—C23—H23	120.1
N5—C6—H6B	108.9	C22—C23—H23	120.1
C7—C6—H6B	108.9	C25—C24—C23	120.3 (3)
H6A—C6—H6B	107.7	C25—C24—H24	119.8
C27—C7—C7A	120.7 (2)	C23—C24—H24	119.8
C27—C7—C6	126.6 (2)	C24—C25—C26	119.3 (3)
C7A—C7—C6	112.69 (19)	C24—C25—H25	120.4
N1—C7A—C7	123.8 (2)	C26—C25—H25	120.4
N1—C7A—C3A	114.9 (2)	C21—C26—C25	122.1 (3)
C7—C7A—C3A	121.2 (2)	C21—C26—H26	119.0
C13—C8—C9	118.6 (2)	C25—C26—H26	119.0
C13—C8—N2	119.9 (2)	C7—C27—C28	130.2 (2)
C9—C8—N2	121.5 (2)	C7—C27—H27	114.9
C10—C9—C8	120.0 (2)	C28—C27—H27	114.9
C10—C9—H9	120.0	C33—C28—C29	115.5 (2)
C8—C9—H9	120.0	C33—C28—C27	122.7 (2)
C11—C10—C9	121.4 (2)	C29—C28—C27	121.6 (2)
C11—C10—H10	119.3	C30—C29—C28	122.9 (2)
C9—C10—H10	119.3	C30—C29—Cl2	117.43 (18)
C10—C11—C12	118.5 (3)	C28—C29—Cl2	119.63 (17)
C10—C11—H11	120.7	C31—C30—C29	119.4 (2)
C12—C11—H11	120.7	C31—C30—H30	120.3
C13—C12—C11	121.1 (3)	C29—C30—H30	120.3
C13—C12—H12	119.5	C32—C31—C30	119.6 (2)
C11—C12—H12	119.5	C32—C31—H31	120.2
C12—C13—C8	120.4 (2)	C30—C31—H31	120.2
C12—C13—H13	119.8	C31—C32—C33	120.7 (2)
C8—C13—H13	119.8	C31—C32—H32	119.6
C15—C14—C19	116.5 (2)	C33—C32—H32	119.6
C15—C14—C3	123.4 (2)	C32—C33—C28	121.9 (2)
C19—C14—C3	120.10 (19)	C32—C33—H33	119.1
C16—C15—C14	122.2 (2)	C28—C33—H33	119.1
C16—C15—Cl1	117.7 (2)	C7A—N1—N2	107.59 (19)
C14—C15—Cl1	120.18 (18)	C8—N2—N1	115.95 (18)
C17—C16—C15	119.7 (2)	C8—N2—C3	121.56 (17)
C17—C16—H16	120.2	N1—N2—C3	110.18 (17)
C15—C16—H16	120.2	C4—N5—C20	110.11 (18)
C16—C17—C18	119.9 (2)	C4—N5—C6	111.69 (18)
C16—C17—H17	120.1	C20—N5—C6	108.06 (17)

N2—C3—C3A—C7A	18.3 (2)	C26—C21—C22—C23	−0.6 (4)
C14—C3—C3A—C7A	139.43 (18)	C20—C21—C22—C23	179.1 (2)
N2—C3—C3A—C4	137.96 (19)	C21—C22—C23—C24	0.5 (5)
C14—C3—C3A—C4	−100.9 (2)	C22—C23—C24—C25	0.0 (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—C25	0.2 (4)
N5—C6—C7—C27	−141.8 (2)	C20—C21—C26—C25	−179.5 (2)
N5—C6—C7—C7A	39.4 (3)	C24—C25—C26—C21	0.3 (4)
C27—C7—C7A—N1	−36.8 (3)	C7A—C7—C27—C28	172.6 (2)
C6—C7—C7A—N1	142.1 (2)	C6—C7—C27—C28	−6.1 (4)
C27—C7—C7A—C3A	147.8 (2)	C7—C27—C28—C33	−31.2 (4)
C6—C7—C7A—C3A	−33.3 (3)	C7—C27—C28—C29	153.8 (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—C30	174.7 (2)
C4—C3A—C7A—C7	40.4 (3)	C33—C28—C29—Cl2	178.85 (18)
C3—C3A—C7A—C7	164.53 (19)	C27—C28—C29—Cl2	−5.9 (3)
C13—C8—C9—C10	−0.4 (3)	C28—C29—C30—C31	0.9 (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—C12	1.1 (4)	C30—C31—C32—C33	−0.8 (4)
C10—C11—C12—C13	−0.6 (4)	C31—C32—C33—C28	1.1 (4)
C11—C12—C13—C8	−0.3 (4)	C29—C28—C33—C32	−0.4 (4)
C9—C8—C13—C12	0.8 (3)	C27—C28—C33—C32	−175.6 (2)
N2—C8—C13—C12	178.6 (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—C15	103.9 (3)	C13—C8—N2—N1	35.8 (3)
N2—C3—C14—C19	39.0 (3)	C9—C8—N2—N1	−146.42 (19)
C3A—C3—C14—C19	−76.6 (3)	C13—C8—N2—C3	174.33 (19)
C19—C14—C15—C16	−1.5 (4)	C9—C8—N2—C3	−7.9 (3)
C3—C14—C15—C16	178.0 (2)	C7A—N1—N2—C8	158.2 (2)
C19—C14—C15—Cl1	179.33 (19)	C7A—N1—N2—C3	15.1 (2)
C3—C14—C15—Cl1	−1.2 (3)	C14—C3—N2—C8	74.5 (2)
C14—C15—C16—C17	0.3 (4)	C3A—C3—N2—C8	−161.78 (18)
Cl1—C15—C16—C17	179.5 (2)	C14—C3—N2—N1	−144.89 (18)
C15—C16—C17—C18	1.3 (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—C14	0.6 (4)	C3A—C4—N5—C6	63.4 (2)
C15—C14—C19—C18	1.1 (4)	C21—C20—N5—C4	61.7 (3)
C3—C14—C19—C18	−178.5 (2)	C21—C20—N5—C6	−176.1 (2)
N5—C20—C21—C26	59.8 (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, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cl1	0.98	2.61	3.101 (2)	111
C27—H27···Cl2	0.93	2.68	3.043 (3)	104

Experimental details

Crystal data
Chemical formula	C₃₂H₂₇Cl₂N₃
M_r	524.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	13.7117 (7), 15.4451 (6), 13.6896 (9)
β (°)	113.135 (7)
V (Å³)	2666.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.36 × 0.26 × 0.22

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.909, 0.943
No. of measured, independent and observed [I > 2σ(I)] reflections	11774, 5436, 2483
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.098, 0.83
No. of reflections	5436
No. of parameters	334
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.23

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cl1	0.98	2.61	3.101 (2)	111
C27—H27···Cl2	0.93	2.68	3.043 (3)	104

Acknowledgements

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.

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Krapcho, J. & Turk, C. F. (1975). US Patent No. 3 923 816. Google Scholar
Nagaraj, B., Narasimhamurthy, T., Yathirajan, H. S., Nagaraja, P., Narasegowda, R. S. & Rathore, R. S. (2005). Acta Cryst. C61, o177–o180. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Noman, A., Rehman, M. M., Bishop, R., Craig, D. C. & Scudder, M. L. (2004). J. Org. Biomol. Chem. 2, 175–182. Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 7| July 2010| Page o1734

doi:10.1107/S1600536810023317

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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