(7E)-5-Benzyl-7-(2-chloro-benzyl-idene)-3-(2-chloro-phen-yl)-2-phenyl-3,3a,4,5,6,7-hexa-hydro-2H-pyrazolo-[4,3-c]pyridine.

In the title 2H-pyrazolo-[4,3-c]pyridine derivative, C(32)H(27)Cl(2)N(3), the dihydro-pyrazole ring adopts an envelope conformation and the piperidine fused ring a twisted-chair conformation. Two short intra-molecular C-H⋯Cl contacts are observed. The crystal packing is characterized by dimeric C-Cl⋯π inter-actions 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 = 524.47

Monoclinic,

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 ▶) 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 ▶); 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.

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

C32H27Cl2N3	F(000) = 1096
Mr = 524.47	Dx = 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

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

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(Fo2) + (0.0389P)2] where P = (Fo2 + 2Fc2)/3
5436 reflections	(Δ/σ)max < 0.001
334 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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