3-Benzyl-7-chloro-9-phenyl-2-tosyl-2,3,3a,4,9,9a-hexa-hydro-1H-pyrrolo[3,4-b]quinoline.

In the title compound, C(31)H(29)ClN(2)O(2)S, the pyrrolidine ring adopts an envelope conformation with the methine C atom adjacent to the NH group as the flap atom. The tetra-hydro-pyridine ring has a half-chair conformation. The two rings are trans-fused. The chloro-benzene ring and the adjacent phenyl ring form a dihedral angle of 77.9 (1)°. The benzyl phenyl and the tosyl phenyl rings are oriented at a dihedral angle of 88.0 (1)°. In the crystal, mol-ecules are linked into chains along the a axis by N-H⋯Cl and C-H⋯Cl hydrogen bonds and the adjacent chains are cross-linked via C-H⋯π inter-actions.

Related literature

For the caspase-3 inhibitory, vasorelaxing and anti­leukemic activities of pyrroloquinoline compounds, see: Kravchenko et al. (2005 ▶); Ferlin et al. (2002 ▶); Anderson et al. (1988 ▶). For related structures, see: Sudha et al. (2007 ▶, 2008a ▶,b ▶). For the crystal structure of the unchlorinated analogue, see: Chinnakali et al. (2009 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Duax et al. (1976 ▶).

Experimental

Crystal data

C31H29ClN2O2S

M = 529.07

Orthorhombic,

a = 10.0106 (1) Å

b = 11.8612 (1) Å

c = 21.8256 (2) Å

V = 2591.52 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 100 K

0.28 × 0.25 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.930, T max = 0.962

35839 measured reflections

8047 independent reflections

7259 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.090

S = 1.02

8047 reflections

339 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.31 e Å−3

Absolute structure: Flack (1983 ▶), 3555 Friedel pairs

Flack parameter: 0.02 (4)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045267/hb5197sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045267/hb5197Isup2.hkl

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

C31H29ClN2O2S	F(000) = 1112
Mr = 529.07	Dx = 1.356 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9900 reflections
a = 10.0106 (1) Å	θ = 2.5–29.9°
b = 11.8612 (1) Å	µ = 0.26 mm−1
c = 21.8256 (2) Å	T = 100 K
V = 2591.52 (4) Å3	Block, colourless
Z = 4	0.28 × 0.25 × 0.15 mm

Bruker SMART APEXII CCD area-detector diffractometer	8047 independent reflections
Radiation source: fine-focus sealed tube	7259 reflections with I > 2σ(I)
graphite	Rint = 0.045
φ and ω scans	θmax = 30.7°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→14
Tmin = 0.930, Tmax = 0.962	k = −17→17
35839 measured reflections	l = −31→30

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0502P)2 + 0.3209P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
8047 reflections	Δρmax = 0.42 e Å−3
339 parameters	Δρmin = −0.31 e Å−3
0 restraints	Absolute structure: Flack (1983), 3555 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (4)

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
Cl1	0.99020 (3)	0.23630 (3)	0.611010 (16)	0.01750 (8)
S1	0.87572 (4)	0.74890 (3)	0.237629 (16)	0.01701 (8)
O1	1.00459 (12)	0.75400 (9)	0.20897 (5)	0.0229 (2)
O2	0.75758 (13)	0.75019 (10)	0.20046 (5)	0.0256 (2)
N1	0.87251 (14)	0.63195 (10)	0.27756 (6)	0.0150 (2)
N2	0.72707 (13)	0.48831 (11)	0.40955 (6)	0.0159 (2)
H1N2	0.654 (2)	0.4565 (17)	0.4026 (10)	0.027 (5)*
C1	0.99589 (16)	0.60584 (12)	0.31441 (7)	0.0160 (3)
H1A	1.0509	0.6725	0.3196	0.019*
H1B	1.0486	0.5472	0.2950	0.019*
C2	0.94008 (14)	0.56589 (12)	0.37568 (7)	0.0137 (3)
H2	0.9205	0.6320	0.4011	0.016*
C3	1.02378 (14)	0.48294 (12)	0.41319 (7)	0.0132 (3)
H3	1.0572	0.4246	0.3853	0.016*
C4	0.93338 (14)	0.42593 (12)	0.46062 (7)	0.0131 (3)
C5	0.99179 (15)	0.36541 (11)	0.50869 (7)	0.0142 (3)
H5	1.0843	0.3619	0.5118	0.017*
C6	0.91344 (15)	0.31068 (12)	0.55164 (7)	0.0141 (3)
C7	0.77481 (15)	0.31665 (12)	0.54938 (7)	0.0149 (3)
H7	0.7228	0.2811	0.5789	0.018*
C8	0.71615 (15)	0.37664 (13)	0.50226 (7)	0.0155 (3)
H8	0.6235	0.3817	0.5004	0.019*
C9	0.79311 (14)	0.43009 (12)	0.45709 (7)	0.0134 (3)
C10	0.80912 (14)	0.51222 (12)	0.35619 (7)	0.0133 (3)
H10	0.8266	0.4425	0.3335	0.016*
C11	0.75027 (16)	0.60125 (12)	0.31332 (7)	0.0147 (3)
H11	0.7237	0.6666	0.3379	0.018*
C12	0.86417 (16)	0.86286 (11)	0.28916 (7)	0.0159 (3)
C13	0.73961 (16)	0.90828 (13)	0.30416 (8)	0.0201 (3)
H13	0.6617	0.8776	0.2880	0.024*
C14	0.73412 (16)	0.99983 (13)	0.34358 (8)	0.0212 (3)
H14	0.6516	1.0306	0.3537	0.025*
C15	0.85024 (15)	1.04677 (12)	0.36832 (7)	0.0170 (3)
C16	0.97308 (15)	0.99944 (12)	0.35296 (7)	0.0175 (3)
H16	1.0509	1.0297	0.3694	0.021*
C17	0.98130 (15)	0.90773 (12)	0.31342 (7)	0.0157 (3)
H17	1.0638	0.8768	0.3033	0.019*
C18	0.84443 (18)	1.14674 (14)	0.41044 (8)	0.0236 (3)
H18A	0.9244	1.1907	0.4059	0.035*
H18B	0.8369	1.1212	0.4520	0.035*
H18C	0.7683	1.1922	0.4003	0.035*
C19	1.14346 (15)	0.53881 (12)	0.44351 (7)	0.0158 (3)
C20	1.12450 (17)	0.61970 (14)	0.48937 (7)	0.0217 (3)
H20	1.0382	0.6402	0.5006	0.026*
C21	1.2328 (2)	0.66992 (16)	0.51843 (9)	0.0292 (4)
H21	1.2188	0.7245	0.5483	0.035*
C22	1.36117 (19)	0.63871 (17)	0.50286 (9)	0.0324 (4)
H22	1.4338	0.6714	0.5227	0.039*
C23	1.38142 (17)	0.55904 (16)	0.45789 (10)	0.0318 (4)
H23	1.4680	0.5380	0.4474	0.038*
C24	1.27344 (16)	0.50968 (14)	0.42795 (8)	0.0221 (3)
H24	1.2885	0.4568	0.3973	0.027*
C25	0.62882 (16)	0.56231 (13)	0.27564 (7)	0.0171 (3)
H25A	0.5588	0.5405	0.3040	0.020*
H25B	0.5961	0.6264	0.2525	0.020*
C26	0.65082 (14)	0.46589 (12)	0.23147 (7)	0.0150 (3)
C27	0.65518 (16)	0.35343 (13)	0.25089 (7)	0.0192 (3)
H27	0.6466	0.3369	0.2924	0.023*
C28	0.67212 (16)	0.26635 (13)	0.20928 (8)	0.0237 (3)
H28	0.6760	0.1922	0.2230	0.028*
C29	0.68336 (18)	0.28986 (14)	0.14704 (8)	0.0253 (4)
H29	0.6945	0.2315	0.1190	0.030*
C30	0.67796 (17)	0.40097 (14)	0.12689 (8)	0.0239 (3)
H30	0.6850	0.4171	0.0853	0.029*
C31	0.66208 (16)	0.48796 (13)	0.16892 (7)	0.0189 (3)
H31	0.6589	0.5621	0.1551	0.023*

	U11	U22	U33	U12	U13	U23
Cl1	0.01853 (15)	0.02012 (16)	0.01386 (15)	0.00295 (13)	0.00000 (12)	0.00457 (12)
S1	0.02840 (18)	0.01221 (14)	0.01041 (15)	−0.00087 (15)	−0.00294 (13)	0.00055 (13)
O1	0.0372 (6)	0.0165 (5)	0.0151 (5)	−0.0010 (6)	0.0072 (5)	0.0006 (4)
O2	0.0404 (6)	0.0180 (5)	0.0185 (5)	−0.0022 (5)	−0.0136 (5)	0.0016 (5)
N1	0.0210 (6)	0.0123 (5)	0.0117 (6)	0.0001 (5)	−0.0011 (5)	0.0020 (4)
N2	0.0138 (6)	0.0219 (6)	0.0120 (6)	−0.0002 (5)	−0.0011 (5)	0.0026 (5)
C1	0.0179 (7)	0.0172 (6)	0.0130 (7)	0.0009 (6)	0.0002 (6)	0.0031 (5)
C2	0.0168 (6)	0.0134 (6)	0.0108 (7)	0.0004 (5)	−0.0010 (5)	0.0000 (5)
C3	0.0155 (6)	0.0127 (6)	0.0114 (6)	0.0007 (5)	0.0016 (5)	−0.0006 (5)
C4	0.0146 (6)	0.0124 (6)	0.0121 (7)	−0.0003 (5)	0.0012 (5)	−0.0013 (5)
C5	0.0144 (6)	0.0142 (6)	0.0139 (7)	0.0004 (5)	−0.0002 (5)	−0.0003 (5)
C6	0.0188 (7)	0.0140 (6)	0.0096 (7)	0.0020 (5)	−0.0031 (5)	−0.0001 (5)
C7	0.0164 (7)	0.0161 (6)	0.0121 (7)	−0.0012 (5)	0.0015 (5)	−0.0011 (5)
C8	0.0148 (6)	0.0174 (7)	0.0145 (7)	−0.0009 (5)	0.0002 (5)	−0.0015 (5)
C9	0.0155 (6)	0.0138 (6)	0.0109 (7)	0.0006 (5)	0.0003 (5)	−0.0021 (5)
C10	0.0162 (6)	0.0129 (6)	0.0109 (7)	0.0004 (5)	−0.0014 (5)	0.0002 (5)
C11	0.0187 (7)	0.0141 (6)	0.0112 (7)	0.0016 (5)	−0.0005 (6)	−0.0008 (5)
C12	0.0227 (7)	0.0122 (6)	0.0129 (7)	−0.0002 (5)	−0.0008 (6)	0.0000 (5)
C13	0.0178 (7)	0.0176 (7)	0.0250 (9)	−0.0002 (6)	−0.0048 (6)	−0.0004 (6)
C14	0.0179 (7)	0.0186 (7)	0.0272 (8)	0.0028 (6)	0.0003 (6)	−0.0009 (6)
C15	0.0203 (7)	0.0145 (6)	0.0163 (7)	0.0007 (5)	0.0030 (6)	0.0005 (5)
C16	0.0177 (7)	0.0174 (7)	0.0175 (7)	−0.0021 (5)	−0.0002 (5)	−0.0018 (6)
C17	0.0156 (7)	0.0145 (6)	0.0171 (7)	0.0020 (5)	−0.0002 (6)	−0.0001 (5)
C18	0.0277 (8)	0.0205 (7)	0.0225 (8)	0.0014 (6)	0.0042 (7)	−0.0066 (6)
C19	0.0164 (7)	0.0158 (6)	0.0152 (7)	−0.0012 (5)	−0.0012 (5)	0.0054 (5)
C20	0.0224 (8)	0.0236 (7)	0.0190 (8)	−0.0030 (7)	−0.0015 (6)	−0.0008 (6)
C21	0.0353 (10)	0.0311 (9)	0.0211 (9)	−0.0126 (8)	−0.0070 (7)	−0.0008 (7)
C22	0.0266 (9)	0.0339 (9)	0.0366 (11)	−0.0130 (8)	−0.0166 (8)	0.0158 (8)
C23	0.0153 (7)	0.0314 (9)	0.0486 (12)	0.0014 (7)	−0.0031 (8)	0.0182 (8)
C24	0.0174 (7)	0.0178 (7)	0.0311 (9)	0.0020 (6)	0.0026 (6)	0.0071 (6)
C25	0.0182 (7)	0.0201 (6)	0.0129 (7)	0.0040 (6)	−0.0020 (6)	0.0005 (5)
C26	0.0135 (6)	0.0176 (6)	0.0139 (7)	−0.0005 (5)	−0.0010 (5)	−0.0008 (5)
C27	0.0188 (7)	0.0206 (7)	0.0181 (8)	−0.0038 (6)	0.0006 (6)	0.0030 (6)
C28	0.0229 (7)	0.0157 (7)	0.0325 (9)	−0.0040 (6)	−0.0003 (7)	0.0000 (6)
C29	0.0283 (8)	0.0223 (7)	0.0253 (9)	−0.0029 (6)	−0.0037 (7)	−0.0103 (6)
C30	0.0297 (8)	0.0273 (8)	0.0148 (8)	−0.0015 (7)	−0.0033 (6)	−0.0037 (6)
C31	0.0234 (7)	0.0194 (7)	0.0141 (7)	−0.0009 (6)	−0.0039 (6)	0.0011 (6)

Cl1—C6	1.7459 (15)	C14—C15	1.397 (2)
S1—O2	1.4341 (12)	C14—H14	0.93
S1—O1	1.4349 (12)	C15—C16	1.393 (2)
S1—N1	1.6386 (12)	C15—C18	1.502 (2)
S1—C12	1.7623 (15)	C16—C17	1.391 (2)
N1—C11	1.496 (2)	C16—H16	0.93
N1—C1	1.506 (2)	C17—H17	0.93
N2—C9	1.4107 (19)	C18—H18A	0.96
N2—C10	1.4531 (19)	C18—H18B	0.96
N2—H1N2	0.84 (2)	C18—H18C	0.96
C1—C2	1.525 (2)	C19—C24	1.388 (2)
C1—H1A	0.97	C19—C20	1.399 (2)
C1—H1B	0.97	C20—C21	1.390 (2)
C2—C10	1.518 (2)	C20—H20	0.93
C2—C3	1.530 (2)	C21—C22	1.380 (3)
C2—H2	0.98	C21—H21	0.93
C3—C19	1.521 (2)	C22—C23	1.377 (3)
C3—C4	1.532 (2)	C22—H22	0.93
C3—H3	0.98	C23—C24	1.392 (3)
C4—C5	1.399 (2)	C23—H23	0.93
C4—C9	1.4072 (19)	C24—H24	0.93
C5—C6	1.384 (2)	C25—C26	1.512 (2)
C5—H5	0.93	C25—H25A	0.97
C6—C7	1.390 (2)	C25—H25B	0.97
C7—C8	1.382 (2)	C26—C31	1.394 (2)
C7—H7	0.93	C26—C27	1.400 (2)
C8—C9	1.403 (2)	C27—C28	1.386 (2)
C8—H8	0.93	C27—H27	0.93
C10—C11	1.529 (2)	C28—C29	1.391 (3)
C10—H10	0.98	C28—H28	0.93
C11—C25	1.539 (2)	C29—C30	1.390 (2)
C11—H11	0.98	C29—H29	0.93
C12—C17	1.392 (2)	C30—C31	1.390 (2)
C12—C13	1.397 (2)	C30—H30	0.93
C13—C14	1.386 (2)	C31—H31	0.93
C13—H13	0.93
O2—S1—O1	119.63 (7)	C14—C13—C12	118.86 (15)
O2—S1—N1	107.08 (7)	C14—C13—H13	120.6
O1—S1—N1	106.57 (7)	C12—C13—H13	120.6
O2—S1—C12	107.38 (7)	C13—C14—C15	121.25 (15)
O1—S1—C12	107.75 (7)	C13—C14—H14	119.4
N1—S1—C12	107.97 (7)	C15—C14—H14	119.4
C11—N1—C1	110.00 (11)	C16—C15—C14	118.75 (14)
C11—N1—S1	119.97 (10)	C16—C15—C18	119.99 (14)
C1—N1—S1	116.23 (10)	C14—C15—C18	121.27 (14)
C9—N2—C10	114.84 (12)	C17—C16—C15	121.11 (14)
C9—N2—H1N2	108.8 (14)	C17—C16—H16	119.4
C10—N2—H1N2	115.8 (14)	C15—C16—H16	119.4
N1—C1—C2	103.40 (12)	C16—C17—C12	119.01 (14)
N1—C1—H1A	111.1	C16—C17—H17	120.5
C2—C1—H1A	111.1	C12—C17—H17	120.5
N1—C1—H1B	111.1	C15—C18—H18A	109.5
C2—C1—H1B	111.1	C15—C18—H18B	109.5
H1A—C1—H1B	109.0	H18A—C18—H18B	109.5
C10—C2—C1	101.60 (12)	C15—C18—H18C	109.5
C10—C2—C3	110.69 (11)	H18A—C18—H18C	109.5
C1—C2—C3	117.94 (12)	H18B—C18—H18C	109.5
C10—C2—H2	108.7	C24—C19—C20	118.21 (15)
C1—C2—H2	108.7	C24—C19—C3	121.56 (14)
C3—C2—H2	108.7	C20—C19—C3	120.21 (13)
C19—C3—C2	112.59 (11)	C21—C20—C19	120.94 (17)
C19—C3—C4	111.32 (12)	C21—C20—H20	119.5
C2—C3—C4	108.78 (12)	C19—C20—H20	119.5
C19—C3—H3	108.0	C22—C21—C20	119.93 (18)
C2—C3—H3	108.0	C22—C21—H21	120.0
C4—C3—H3	108.0	C20—C21—H21	120.0
C5—C4—C9	118.43 (13)	C23—C22—C21	119.78 (17)
C5—C4—C3	119.09 (13)	C23—C22—H22	120.1
C9—C4—C3	122.47 (13)	C21—C22—H22	120.1
C6—C5—C4	120.78 (14)	C22—C23—C24	120.57 (17)
C6—C5—H5	119.6	C22—C23—H23	119.7
C4—C5—H5	119.6	C24—C23—H23	119.7
C5—C6—C7	121.18 (14)	C19—C24—C23	120.54 (16)
C5—C6—Cl1	119.37 (11)	C19—C24—H24	119.7
C7—C6—Cl1	119.42 (12)	C23—C24—H24	119.7
C8—C7—C6	118.47 (14)	C26—C25—C11	116.91 (13)
C8—C7—H7	120.8	C26—C25—H25A	108.1
C6—C7—H7	120.8	C11—C25—H25A	108.1
C7—C8—C9	121.50 (14)	C26—C25—H25B	108.1
C7—C8—H8	119.2	C11—C25—H25B	108.1
C9—C8—H8	119.2	H25A—C25—H25B	107.3
C8—C9—C4	119.59 (14)	C31—C26—C27	118.21 (14)
C8—C9—N2	118.73 (13)	C31—C26—C25	119.60 (13)
C4—C9—N2	121.67 (13)	C27—C26—C25	122.14 (14)
N2—C10—C2	110.21 (12)	C28—C27—C26	121.02 (15)
N2—C10—C11	114.05 (12)	C28—C27—H27	119.5
C2—C10—C11	102.39 (11)	C26—C27—H27	119.5
N2—C10—H10	110.0	C27—C28—C29	120.02 (15)
C2—C10—H10	110.0	C27—C28—H28	120.0
C11—C10—H10	110.0	C29—C28—H28	120.0
N1—C11—C10	99.92 (12)	C30—C29—C28	119.71 (16)
N1—C11—C25	116.13 (12)	C30—C29—H29	120.1
C10—C11—C25	115.10 (12)	C28—C29—H29	120.1
N1—C11—H11	108.4	C31—C30—C29	119.96 (16)
C10—C11—H11	108.4	C31—C30—H30	120.0
C25—C11—H11	108.4	C29—C30—H30	120.0
C17—C12—C13	121.01 (13)	C30—C31—C26	121.07 (14)
C17—C12—S1	118.72 (12)	C30—C31—H31	119.5
C13—C12—S1	120.25 (12)	C26—C31—H31	119.5
O2—S1—N1—C11	−50.80 (12)	C2—C10—C11—N1	43.40 (13)
O1—S1—N1—C11	−179.92 (10)	N2—C10—C11—C25	−72.42 (16)
C12—S1—N1—C11	64.55 (12)	C2—C10—C11—C25	168.55 (12)
O2—S1—N1—C1	172.80 (10)	O2—S1—C12—C17	−155.56 (12)
O1—S1—N1—C1	43.67 (12)	O1—S1—C12—C17	−25.46 (14)
C12—S1—N1—C1	−71.85 (12)	N1—S1—C12—C17	89.29 (13)
C11—N1—C1—C2	−3.90 (14)	O2—S1—C12—C13	23.14 (15)
S1—N1—C1—C2	136.63 (10)	O1—S1—C12—C13	153.24 (12)
N1—C1—C2—C10	30.84 (14)	N1—S1—C12—C13	−92.01 (13)
N1—C1—C2—C3	151.97 (12)	C17—C12—C13—C14	0.4 (2)
C10—C2—C3—C19	−169.50 (12)	S1—C12—C13—C14	−178.31 (12)
C1—C2—C3—C19	74.18 (16)	C12—C13—C14—C15	−0.1 (2)
C10—C2—C3—C4	−45.62 (15)	C13—C14—C15—C16	−0.4 (2)
C1—C2—C3—C4	−161.95 (12)	C13—C14—C15—C18	179.29 (15)
C19—C3—C4—C5	−41.60 (17)	C14—C15—C16—C17	0.5 (2)
C2—C3—C4—C5	−166.23 (12)	C18—C15—C16—C17	−179.16 (14)
C19—C3—C4—C9	139.71 (14)	C15—C16—C17—C12	−0.2 (2)
C2—C3—C4—C9	15.08 (19)	C13—C12—C17—C16	−0.2 (2)
C9—C4—C5—C6	0.2 (2)	S1—C12—C17—C16	178.46 (11)
C3—C4—C5—C6	−178.56 (13)	C2—C3—C19—C24	−115.72 (15)
C4—C5—C6—C7	−1.8 (2)	C4—C3—C19—C24	121.83 (15)
C4—C5—C6—Cl1	−179.87 (11)	C2—C3—C19—C20	65.90 (17)
C5—C6—C7—C8	1.5 (2)	C4—C3—C19—C20	−56.56 (17)
Cl1—C6—C7—C8	179.53 (11)	C24—C19—C20—C21	0.2 (2)
C6—C7—C8—C9	0.5 (2)	C3—C19—C20—C21	178.68 (15)
C7—C8—C9—C4	−2.1 (2)	C19—C20—C21—C22	−1.1 (3)
C7—C8—C9—N2	178.85 (14)	C20—C21—C22—C23	1.0 (3)
C5—C4—C9—C8	1.7 (2)	C21—C22—C23—C24	0.0 (3)
C3—C4—C9—C8	−179.61 (12)	C20—C19—C24—C23	0.7 (2)
C5—C4—C9—N2	−179.25 (12)	C3—C19—C24—C23	−177.67 (14)
C3—C4—C9—N2	−0.5 (2)	C22—C23—C24—C19	−0.9 (2)
C10—N2—C9—C8	−162.78 (13)	N1—C11—C25—C26	54.31 (17)
C10—N2—C9—C4	18.1 (2)	C10—C11—C25—C26	−61.90 (18)
C9—N2—C10—C2	−49.72 (16)	C11—C25—C26—C31	−103.37 (17)
C9—N2—C10—C11	−164.22 (12)	C11—C25—C26—C27	79.21 (19)
C1—C2—C10—N2	−168.63 (12)	C31—C26—C27—C28	0.9 (2)
C3—C2—C10—N2	65.30 (15)	C25—C26—C27—C28	178.35 (14)
C1—C2—C10—C11	−46.93 (14)	C26—C27—C28—C29	−0.8 (2)
C3—C2—C10—C11	−172.99 (11)	C27—C28—C29—C30	0.2 (3)
C1—N1—C11—C10	−24.29 (13)	C28—C29—C30—C31	0.3 (3)
S1—N1—C11—C10	−163.12 (9)	C29—C30—C31—C26	−0.3 (3)
C1—N1—C11—C25	−148.72 (12)	C27—C26—C31—C30	−0.4 (2)
S1—N1—C11—C25	72.44 (15)	C25—C26—C31—C30	−177.87 (15)
N2—C10—C11—N1	162.44 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···Cl1i	0.84 (2)	2.83 (2)	3.5947 (13)	153 (2)
C25—H25B···O2	0.97	2.46	3.0529 (19)	119
C27—H27···Cl1i	0.93	2.77	3.5980 (16)	149
C17—H17···Cg2ii	0.93	2.70	3.5403 (16)	151
C29—H29···Cg1iii	0.93	2.68	3.6014 (19)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯Cl1i	0.84 (2)	2.83 (2)	3.5947 (13)	153 (2)
C27—H27⋯Cl1i	0.93	2.77	3.5980 (16)	149
C17—H17⋯Cg2ii	0.93	2.70	3.5403 (16)	151
C29—H29⋯Cg1iii	0.93	2.68	3.6014 (19)	170

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C19–C24 and C26–C31 rings, respectively.