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

In the title compound, C(32)H(32)N(2)O(2)S, the pyrrolidine ring adopts a twist conformation while the tetra-hydro-pyridine ring is in a distorted half-chair conformation. The two rings are trans-fused. The dihedral angle between the sulfonyl and benzyl phenyl rings is 72.54 (14)°. The mol-ecular structure is stabilized by C-H⋯O hydrogen bonds, and N-H⋯π inter-actions involving the benzyl phenyl ring. The screw-related mol-ecules are linked into chains along the b axis by C-H⋯O hydrogen bonds and C-H⋯π inter-actions. Adjacent inversion-related chains inter-act via C-H⋯π inter-actions, forming a two-dimensional network parallel to the bc plane.

Related literature

For the anti­cancer and photochemotherapeutic activity of pyrroloquinoline derivatives, see: Ferlin et al. (2005 ▶); Gasparotto et al. (2007 ▶); Barraja et al. (2003 ▶). For a related structure, see: Sudha et al. (2009 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Duax et al. (1976 ▶).

Experimental

Crystal data

C32H32N2O2S

M = 508.66

Monoclinic,

a = 9.0445 (4) Å

b = 10.6014 (4) Å

c = 27.533 (1) Å

β = 96.294 (3)°

V = 2624.07 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 100 K

0.38 × 0.20 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.360, T max = 0.974

22823 measured reflections

5138 independent reflections

3615 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.178

S = 1.04

5138 reflections

340 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.69 e Å−3

Δρmin = −0.51 e Å−3

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/S1600536809044481/tk2561sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044481/tk2561Isup2.hkl

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

C32H32N2O2S	F(000) = 1080
Mr = 508.66	Dx = 1.288 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5605 reflections
a = 9.0445 (4) Å	θ = 2.3–30.1°
b = 10.6014 (4) Å	µ = 0.16 mm−1
c = 27.533 (1) Å	T = 100 K
β = 96.294 (3)°	Block, colourless
V = 2624.07 (18) Å3	0.38 × 0.20 × 0.17 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	5138 independent reflections
Radiation source: fine-focus sealed tube	3615 reflections with I > 2σ(I)
graphite	Rint = 0.078
φ and ω scans	θmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→11
Tmin = 0.360, Tmax = 0.974	k = −13→12
22823 measured reflections	l = −33→33

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.1011P)2 + 1.1335P] where P = (Fo2 + 2Fc2)/3
5138 reflections	(Δ/σ)max = 0.001
340 parameters	Δρmax = 0.69 e Å−3
0 restraints	Δρmin = −0.50 e Å−3

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
S1	0.62265 (8)	0.48132 (7)	0.13646 (2)	0.0262 (2)
O1	0.4733 (2)	0.4422 (2)	0.12298 (7)	0.0322 (5)
O2	0.6528 (2)	0.58710 (19)	0.16844 (7)	0.0335 (5)
N1	0.7118 (3)	0.3614 (2)	0.16335 (8)	0.0239 (5)
N2	1.0859 (3)	0.2372 (2)	0.15932 (8)	0.0249 (5)
H1N2	1.156 (3)	0.272 (3)	0.1791 (11)	0.022 (7)*
C1	0.6810 (3)	0.2332 (3)	0.14178 (10)	0.0260 (6)
H1A	0.6104	0.2378	0.1126	0.031*
H1B	0.6422	0.1770	0.1651	0.031*
C2	0.8318 (3)	0.1896 (2)	0.12960 (8)	0.0214 (6)
H2	0.8528	0.2304	0.0992	0.026*
C3	0.8577 (3)	0.0474 (2)	0.12508 (9)	0.0217 (6)
H3	0.8140	0.0064	0.1520	0.026*
C4	1.0250 (3)	0.0211 (3)	0.13221 (8)	0.0228 (6)
C5	1.0783 (3)	−0.0993 (3)	0.12259 (9)	0.0264 (6)
H5	1.0096	−0.1616	0.1122	0.032*
C6	1.2275 (3)	−0.1305 (3)	0.12773 (9)	0.0305 (7)
C7	1.3287 (4)	−0.0369 (3)	0.14395 (10)	0.0362 (8)
H7	1.4300	−0.0551	0.1478	0.043*
C8	1.2805 (3)	0.0830 (3)	0.15445 (10)	0.0333 (7)
H8	1.3500	0.1441	0.1655	0.040*
C9	1.1304 (3)	0.1136 (3)	0.14877 (9)	0.0258 (6)
C10	0.9342 (3)	0.2446 (2)	0.17126 (9)	0.0223 (6)
H10	0.9251	0.1957	0.2010	0.027*
C11	0.8745 (3)	0.3775 (2)	0.17768 (9)	0.0214 (6)
H11	0.9149	0.4339	0.1542	0.026*
C12	0.7040 (3)	0.5160 (3)	0.08227 (9)	0.0262 (6)
C13	0.8142 (3)	0.6074 (3)	0.08287 (10)	0.0296 (7)
H13	0.8492	0.6472	0.1120	0.036*
C14	0.8717 (4)	0.6392 (3)	0.03979 (10)	0.0332 (7)
H14	0.9459	0.7000	0.0404	0.040*
C15	0.8201 (3)	0.5815 (3)	−0.00429 (10)	0.0293 (7)
C16	0.7127 (3)	0.4883 (3)	−0.00385 (10)	0.0307 (7)
H16	0.6792	0.4474	−0.0329	0.037*
C17	0.6536 (3)	0.4543 (3)	0.03907 (10)	0.0290 (6)
H17	0.5817	0.3914	0.0388	0.035*
C18	0.8756 (4)	0.6232 (3)	−0.05135 (11)	0.0381 (8)
H18A	0.8361	0.5685	−0.0774	0.057*
H18B	0.9823	0.6194	−0.0481	0.057*
H18C	0.8439	0.7082	−0.0586	0.057*
C19	0.7819 (3)	−0.0079 (2)	0.07772 (9)	0.0219 (6)
C20	0.8280 (3)	0.0268 (3)	0.03263 (9)	0.0270 (6)
H20	0.9051	0.0844	0.0316	0.032*
C21	0.7597 (3)	−0.0241 (3)	−0.01055 (10)	0.0305 (7)
H21	0.7916	−0.0010	−0.0403	0.037*
C22	0.6438 (3)	−0.1093 (3)	−0.00949 (11)	0.0327 (7)
H22	0.5974	−0.1428	−0.0385	0.039*
C23	0.5976 (3)	−0.1444 (3)	0.03477 (11)	0.0329 (7)
H23	0.5202	−0.2018	0.0357	0.040*
C24	0.6674 (3)	−0.0936 (3)	0.07798 (10)	0.0276 (6)
H24	0.6360	−0.1180	0.1076	0.033*
C25	0.9111 (3)	0.4321 (3)	0.22950 (9)	0.0261 (6)
H25A	0.8648	0.5142	0.2315	0.031*
H25B	0.8722	0.3769	0.2532	0.031*
C26	1.0768 (3)	0.4441 (3)	0.24082 (9)	0.0257 (6)
C27	1.1623 (3)	0.3525 (3)	0.26768 (9)	0.0263 (6)
H27	1.1146	0.2873	0.2823	0.032*
C28	1.3159 (4)	0.3569 (3)	0.27287 (9)	0.0307 (7)
H28	1.3702	0.2939	0.2903	0.037*
C29	1.3898 (3)	0.4552 (3)	0.25217 (10)	0.0332 (7)
H29	1.4932	0.4583	0.2556	0.040*
C30	1.3068 (4)	0.5486 (3)	0.22638 (10)	0.0342 (7)
H30	1.3549	0.6153	0.2128	0.041*
C31	1.1532 (3)	0.5429 (3)	0.22085 (9)	0.0293 (7)
H31	1.0993	0.6062	0.2035	0.035*
C32	1.2786 (4)	−0.2591 (3)	0.11267 (11)	0.0403 (8)
H32A	1.2094	−0.3220	0.1210	0.060*
H32B	1.3752	−0.2767	0.1294	0.060*
H32C	1.2837	−0.2603	0.0780	0.060*

	U11	U22	U33	U12	U13	U23
S1	0.0340 (4)	0.0233 (4)	0.0212 (3)	0.0093 (3)	0.0028 (3)	−0.0022 (3)
O1	0.0324 (12)	0.0364 (12)	0.0282 (10)	0.0140 (9)	0.0044 (8)	0.0006 (9)
O2	0.0486 (13)	0.0266 (11)	0.0254 (10)	0.0114 (9)	0.0040 (9)	−0.0076 (8)
N1	0.0294 (13)	0.0202 (12)	0.0219 (11)	0.0044 (9)	0.0023 (9)	0.0017 (9)
N2	0.0245 (13)	0.0277 (13)	0.0221 (11)	0.0020 (10)	0.0007 (10)	−0.0082 (10)
C1	0.0295 (16)	0.0213 (15)	0.0268 (14)	0.0015 (12)	0.0015 (11)	−0.0008 (11)
C2	0.0293 (15)	0.0188 (14)	0.0161 (12)	0.0011 (11)	0.0033 (11)	0.0033 (10)
C3	0.0303 (16)	0.0183 (14)	0.0170 (12)	0.0010 (11)	0.0054 (10)	0.0038 (10)
C4	0.0305 (16)	0.0250 (15)	0.0127 (11)	0.0046 (12)	0.0018 (10)	0.0019 (10)
C5	0.0384 (17)	0.0252 (15)	0.0153 (12)	0.0051 (12)	0.0015 (11)	0.0047 (10)
C6	0.0436 (19)	0.0342 (17)	0.0134 (12)	0.0147 (14)	0.0012 (12)	0.0039 (11)
C7	0.0331 (18)	0.054 (2)	0.0205 (13)	0.0201 (15)	−0.0019 (12)	−0.0069 (13)
C8	0.0294 (17)	0.048 (2)	0.0214 (13)	0.0040 (14)	−0.0010 (12)	−0.0121 (13)
C9	0.0318 (16)	0.0328 (16)	0.0125 (11)	0.0063 (12)	0.0013 (11)	−0.0017 (11)
C10	0.0297 (16)	0.0212 (14)	0.0163 (12)	0.0029 (11)	0.0035 (10)	0.0008 (10)
C11	0.0271 (15)	0.0193 (14)	0.0177 (12)	0.0027 (11)	0.0015 (10)	0.0010 (10)
C12	0.0345 (17)	0.0234 (15)	0.0206 (12)	0.0089 (12)	0.0023 (11)	0.0016 (11)
C13	0.0454 (19)	0.0191 (14)	0.0231 (13)	0.0035 (13)	−0.0016 (12)	0.0006 (11)
C14	0.0408 (19)	0.0254 (16)	0.0326 (15)	0.0012 (13)	0.0004 (13)	0.0060 (12)
C15	0.0352 (17)	0.0258 (16)	0.0269 (14)	0.0114 (13)	0.0029 (12)	0.0032 (11)
C16	0.0402 (18)	0.0306 (16)	0.0206 (13)	0.0107 (13)	−0.0001 (12)	−0.0049 (11)
C17	0.0324 (17)	0.0258 (16)	0.0281 (14)	0.0046 (12)	−0.0006 (12)	−0.0029 (11)
C18	0.048 (2)	0.0374 (18)	0.0297 (15)	0.0112 (15)	0.0075 (14)	0.0067 (13)
C19	0.0264 (15)	0.0167 (13)	0.0223 (12)	0.0039 (11)	0.0013 (11)	0.0025 (10)
C20	0.0370 (17)	0.0226 (15)	0.0212 (13)	−0.0017 (12)	0.0022 (11)	0.0005 (11)
C21	0.0390 (18)	0.0312 (16)	0.0207 (13)	0.0076 (13)	0.0009 (12)	0.0016 (12)
C22	0.0355 (18)	0.0304 (16)	0.0295 (14)	0.0064 (13)	−0.0091 (12)	−0.0080 (12)
C23	0.0290 (17)	0.0281 (17)	0.0401 (16)	−0.0035 (12)	−0.0034 (13)	−0.0031 (13)
C24	0.0324 (17)	0.0234 (15)	0.0275 (14)	0.0017 (12)	0.0053 (12)	−0.0008 (11)
C25	0.0360 (17)	0.0225 (14)	0.0201 (13)	0.0025 (12)	0.0045 (11)	−0.0036 (11)
C26	0.0376 (17)	0.0241 (15)	0.0159 (12)	0.0001 (12)	0.0048 (11)	−0.0054 (10)
C27	0.0417 (18)	0.0212 (14)	0.0152 (12)	−0.0024 (12)	−0.0006 (11)	−0.0024 (10)
C28	0.0417 (19)	0.0287 (16)	0.0203 (13)	0.0059 (13)	−0.0035 (12)	−0.0023 (11)
C29	0.0324 (17)	0.0429 (19)	0.0236 (14)	−0.0015 (14)	−0.0002 (12)	−0.0016 (13)
C30	0.046 (2)	0.0344 (18)	0.0225 (13)	−0.0070 (14)	0.0031 (13)	0.0022 (12)
C31	0.0433 (19)	0.0231 (15)	0.0208 (13)	0.0022 (13)	0.0006 (12)	−0.0008 (11)
C32	0.053 (2)	0.0387 (19)	0.0301 (15)	0.0231 (15)	0.0078 (14)	0.0043 (13)

S1—O1	1.423 (2)	C14—H14	0.93
S1—O2	1.433 (2)	C15—C16	1.387 (4)
S1—N1	1.638 (2)	C15—C18	1.506 (4)
S1—C12	1.773 (3)	C16—C17	1.397 (4)
N1—C11	1.491 (3)	C16—H16	0.93
N1—C1	1.497 (3)	C17—H17	0.93
N2—C9	1.410 (4)	C18—H18A	0.96
N2—C10	1.448 (3)	C18—H18B	0.96
N2—H1N2	0.87 (3)	C18—H18C	0.96
C1—C2	1.512 (4)	C19—C24	1.379 (4)
C1—H1A	0.97	C19—C20	1.401 (4)
C1—H1B	0.97	C20—C21	1.388 (4)
C2—C10	1.510 (4)	C20—H20	0.93
C2—C3	1.532 (4)	C21—C22	1.386 (4)
C2—H2	0.98	C21—H21	0.93
C3—C19	1.522 (4)	C22—C23	1.382 (4)
C3—C4	1.530 (4)	C22—H22	0.93
C3—H3	0.98	C23—C24	1.392 (4)
C4—C5	1.400 (4)	C23—H23	0.93
C4—C9	1.408 (4)	C24—H24	0.93
C5—C6	1.382 (4)	C25—C26	1.502 (4)
C5—H5	0.93	C25—H25A	0.97
C6—C7	1.391 (5)	C25—H25B	0.97
C6—C32	1.512 (4)	C26—C31	1.400 (4)
C7—C8	1.385 (4)	C26—C27	1.401 (4)
C7—H7	0.93	C27—C28	1.381 (4)
C8—C9	1.388 (4)	C27—H27	0.93
C8—H8	0.93	C28—C29	1.394 (4)
C10—C11	1.527 (4)	C28—H28	0.93
C10—H10	0.98	C29—C30	1.390 (4)
C11—C25	1.541 (3)	C29—H29	0.93
C11—H11	0.98	C30—C31	1.383 (4)
C12—C13	1.389 (4)	C30—H30	0.93
C12—C17	1.390 (4)	C31—H31	0.93
C13—C14	1.388 (4)	C32—H32A	0.96
C13—H13	0.93	C32—H32B	0.96
C14—C15	1.393 (4)	C32—H32C	0.96
O1—S1—O2	119.99 (12)	C13—C14—C15	121.1 (3)
O1—S1—N1	107.33 (12)	C13—C14—H14	119.4
O2—S1—N1	106.16 (12)	C15—C14—H14	119.4
O1—S1—C12	108.10 (13)	C16—C15—C14	118.2 (3)
O2—S1—C12	106.62 (13)	C16—C15—C18	121.1 (3)
N1—S1—C12	108.18 (12)	C14—C15—C18	120.6 (3)
C11—N1—C1	110.2 (2)	C15—C16—C17	121.7 (3)
C11—N1—S1	116.96 (17)	C15—C16—H16	119.2
C1—N1—S1	117.64 (17)	C17—C16—H16	119.2
C9—N2—C10	113.3 (2)	C12—C17—C16	118.8 (3)
C9—N2—H1N2	108.1 (19)	C12—C17—H17	120.6
C10—N2—H1N2	118.8 (19)	C16—C17—H17	120.6
N1—C1—C2	103.4 (2)	C15—C18—H18A	109.5
N1—C1—H1A	111.1	C15—C18—H18B	109.5
C2—C1—H1A	111.1	H18A—C18—H18B	109.5
N1—C1—H1B	111.1	C15—C18—H18C	109.5
C2—C1—H1B	111.1	H18A—C18—H18C	109.5
H1A—C1—H1B	109.0	H18B—C18—H18C	109.5
C10—C2—C1	101.9 (2)	C24—C19—C20	118.3 (2)
C10—C2—C3	110.8 (2)	C24—C19—C3	121.1 (2)
C1—C2—C3	117.9 (2)	C20—C19—C3	120.6 (2)
C10—C2—H2	108.6	C21—C20—C19	120.6 (3)
C1—C2—H2	108.6	C21—C20—H20	119.7
C3—C2—H2	108.6	C19—C20—H20	119.7
C19—C3—C4	112.7 (2)	C22—C21—C20	120.1 (3)
C19—C3—C2	113.0 (2)	C22—C21—H21	119.9
C4—C3—C2	109.1 (2)	C20—C21—H21	119.9
C19—C3—H3	107.3	C23—C22—C21	119.8 (3)
C4—C3—H3	107.3	C23—C22—H22	120.1
C2—C3—H3	107.3	C21—C22—H22	120.1
C5—C4—C9	117.5 (3)	C22—C23—C24	119.8 (3)
C5—C4—C3	119.9 (2)	C22—C23—H23	120.1
C9—C4—C3	122.6 (2)	C24—C23—H23	120.1
C6—C5—C4	123.5 (3)	C19—C24—C23	121.4 (3)
C6—C5—H5	118.3	C19—C24—H24	119.3
C4—C5—H5	118.3	C23—C24—H24	119.3
C5—C6—C7	117.6 (3)	C26—C25—C11	109.4 (2)
C5—C6—C32	120.8 (3)	C26—C25—H25A	109.8
C7—C6—C32	121.4 (3)	C11—C25—H25A	109.8
C8—C7—C6	120.7 (3)	C26—C25—H25B	109.8
C8—C7—H7	119.6	C11—C25—H25B	109.8
C6—C7—H7	119.6	H25A—C25—H25B	108.2
C7—C8—C9	121.2 (3)	C31—C26—C27	117.3 (3)
C7—C8—H8	119.4	C31—C26—C25	120.4 (2)
C9—C8—H8	119.4	C27—C26—C25	122.1 (3)
C8—C9—C4	119.5 (3)	C28—C27—C26	121.5 (3)
C8—C9—N2	119.5 (3)	C28—C27—H27	119.2
C4—C9—N2	121.0 (3)	C26—C27—H27	119.2
N2—C10—C2	108.9 (2)	C27—C28—C29	120.3 (3)
N2—C10—C11	115.6 (2)	C27—C28—H28	119.9
C2—C10—C11	104.4 (2)	C29—C28—H28	119.9
N2—C10—H10	109.2	C30—C29—C28	119.1 (3)
C2—C10—H10	109.2	C30—C29—H29	120.5
C11—C10—H10	109.2	C28—C29—H29	120.5
N1—C11—C10	102.4 (2)	C31—C30—C29	120.3 (3)
N1—C11—C25	113.2 (2)	C31—C30—H30	119.8
C10—C11—C25	114.3 (2)	C29—C30—H30	119.8
N1—C11—H11	108.9	C30—C31—C26	121.5 (3)
C10—C11—H11	108.9	C30—C31—H31	119.2
C25—C11—H11	108.9	C26—C31—H31	119.2
C13—C12—C17	120.4 (2)	C6—C32—H32A	109.5
C13—C12—S1	119.9 (2)	C6—C32—H32B	109.5
C17—C12—S1	119.7 (2)	H32A—C32—H32B	109.5
C14—C13—C12	119.7 (3)	C6—C32—H32C	109.5
C14—C13—H13	120.2	H32A—C32—H32C	109.5
C12—C13—H13	120.2	H32B—C32—H32C	109.5
O1—S1—N1—C11	175.82 (17)	C2—C10—C11—N1	31.8 (2)
O2—S1—N1—C11	−54.7 (2)	N2—C10—C11—C25	−85.8 (3)
C12—S1—N1—C11	59.4 (2)	C2—C10—C11—C25	154.5 (2)
O1—S1—N1—C1	41.1 (2)	O1—S1—C12—C13	149.6 (2)
O2—S1—N1—C1	170.60 (19)	O2—S1—C12—C13	19.4 (3)
C12—S1—N1—C1	−75.3 (2)	N1—S1—C12—C13	−94.4 (2)
C11—N1—C1—C2	−16.8 (3)	O1—S1—C12—C17	−28.3 (3)
S1—N1—C1—C2	120.77 (19)	O2—S1—C12—C17	−158.5 (2)
N1—C1—C2—C10	35.8 (2)	N1—S1—C12—C17	87.6 (2)
N1—C1—C2—C3	157.3 (2)	C17—C12—C13—C14	1.5 (4)
C10—C2—C3—C19	−167.9 (2)	S1—C12—C13—C14	−176.5 (2)
C1—C2—C3—C19	75.3 (3)	C12—C13—C14—C15	0.4 (4)
C10—C2—C3—C4	−41.8 (3)	C13—C14—C15—C16	−2.0 (4)
C1—C2—C3—C4	−158.6 (2)	C13—C14—C15—C18	175.7 (3)
C19—C3—C4—C5	−44.2 (3)	C14—C15—C16—C17	1.7 (4)
C2—C3—C4—C5	−170.5 (2)	C18—C15—C16—C17	−175.9 (3)
C19—C3—C4—C9	136.4 (2)	C13—C12—C17—C16	−1.7 (4)
C2—C3—C4—C9	10.1 (3)	S1—C12—C17—C16	176.2 (2)
C9—C4—C5—C6	−1.1 (4)	C15—C16—C17—C12	0.1 (4)
C3—C4—C5—C6	179.5 (2)	C4—C3—C19—C24	121.5 (3)
C4—C5—C6—C7	0.9 (4)	C2—C3—C19—C24	−114.3 (3)
C4—C5—C6—C32	−174.8 (2)	C4—C3—C19—C20	−58.1 (3)
C5—C6—C7—C8	0.0 (4)	C2—C3—C19—C20	66.1 (3)
C32—C6—C7—C8	175.6 (3)	C24—C19—C20—C21	0.0 (4)
C6—C7—C8—C9	−0.5 (4)	C3—C19—C20—C21	179.6 (2)
C7—C8—C9—C4	0.2 (4)	C19—C20—C21—C22	0.5 (4)
C7—C8—C9—N2	−179.3 (3)	C20—C21—C22—C23	−0.6 (4)
C5—C4—C9—C8	0.5 (3)	C21—C22—C23—C24	0.2 (5)
C3—C4—C9—C8	179.9 (2)	C20—C19—C24—C23	−0.4 (4)
C5—C4—C9—N2	−179.9 (2)	C3—C19—C24—C23	179.9 (3)
C3—C4—C9—N2	−0.6 (4)	C22—C23—C24—C19	0.3 (4)
C10—N2—C9—C8	−156.3 (2)	N1—C11—C25—C26	179.6 (2)
C10—N2—C9—C4	24.2 (3)	C10—C11—C25—C26	62.9 (3)
C9—N2—C10—C2	−56.6 (3)	C11—C25—C26—C31	76.8 (3)
C9—N2—C10—C11	−173.7 (2)	C11—C25—C26—C27	−97.3 (3)
C1—C2—C10—N2	−166.6 (2)	C31—C26—C27—C28	−2.2 (4)
C3—C2—C10—N2	67.1 (3)	C25—C26—C27—C28	172.1 (2)
C1—C2—C10—C11	−42.5 (2)	C26—C27—C28—C29	1.5 (4)
C3—C2—C10—C11	−168.8 (2)	C27—C28—C29—C30	0.1 (4)
C1—N1—C11—C10	−9.1 (2)	C28—C29—C30—C31	−0.8 (4)
S1—N1—C11—C10	−146.95 (17)	C29—C30—C31—C26	0.0 (4)
C1—N1—C11—C25	−132.6 (2)	C27—C26—C31—C30	1.5 (4)
S1—N1—C11—C25	89.6 (2)	C25—C26—C31—C30	−173.0 (2)
N2—C10—C11—N1	151.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1	0.97	2.53	2.914 (4)	104
C13—H13···O2	0.93	2.57	2.912 (3)	103
C25—H25A···O2	0.97	2.56	3.182 (3)	122
C28—H28···O2i	0.93	2.49	3.282 (4)	143
N2—H1N2···Cg3	0.87 (3)	2.69 (3)	3.461 (3)	148 (2)
C3—H3···Cg3i	0.98	2.93	3.852 (3)	158
C18—H18B···Cg2ii	0.96	2.90	3.723 (4)	145
C21—H21···Cg1iii	0.93	2.74	3.637 (3)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C25—H25A⋯O2	0.97	2.56	3.182 (3)	122
C28—H28⋯O2i	0.93	2.49	3.282 (4)	143
N2—H1N2⋯Cg3	0.87 (3)	2.69 (3)	3.461 (3)	148 (2)
C3—H3⋯Cg3i	0.98	2.93	3.852 (3)	158
C18—H18B⋯Cg2ii	0.96	2.90	3.723 (4)	145
C21—H21⋯Cg1iii	0.93	2.74	3.637 (3)	162

Symmetry codes: (i) ; (ii) ; (iii) . Cg1, Cg2 and Cg3 are the centroids of the C4–C9, C12–C17 and C26–C31 rings, respectively.