3-Benzyl-7-meth-oxy-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(3)S, the pyrrolidine ring adopts an envelope conformation with the methine C atom nearest to the phenyl ring as the flap atom. The tetra-hydro-pyridine ring has a half-chair conformation. The two rings are trans-fused. The phenyl ring bound to the tetra-hydro-pyridine is oriented almost perpendicular [dihedral angle = 86.35 (10)°] to the fused benzene ring. The dihedral angle between the benzyl-phenyl ring and the sulfonyl-bound phenyl ring is 69.43 (10)°. A very weak N-H⋯π inter-action is observed in the mol-ecular structure. In the crystal, mol-ecules translated one unit along the b axis are linked into C(10) chains by C-H⋯O hydrogen bonds; adjacent chains are linked via C-H⋯π inter-actions, forming a two-dimensional network parallel to the bc plane.

Related literature

For biological activity of pyrroloquinoline derivatives, see: Ryu et al. (2009 ▶); Tsuji et al. (1995 ▶); Ferlin et al. (2001 ▶). For related structures, see: Sudha et al. (2007 ▶, 2008a ▶,b ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Duax et al. (1976 ▶).

Experimental

Crystal data

C32H32N2O3S

M = 524.66

Monoclinic,

a = 21.5063 (9) Å

b = 11.6188 (5) Å

c = 10.7616 (4) Å

β = 98.219 (2)°

V = 2661.46 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 100 K

0.32 × 0.30 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.636, T max = 0.987

28181 measured reflections

6088 independent reflections

4661 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.155

S = 1.02

6088 reflections

349 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.54 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/S1600536809044973/lh2940sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044973/lh2940Isup2.hkl

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

C32H32N2O3S	F(000) = 1112
Mr = 524.66	Dx = 1.309 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6305 reflections
a = 21.5063 (9) Å	θ = 2.6–28.5°
b = 11.6188 (5) Å	µ = 0.16 mm−1
c = 10.7616 (4) Å	T = 100 K
β = 98.219 (2)°	Plate, colourless
V = 2661.46 (19) Å3	0.32 × 0.30 × 0.08 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	6088 independent reflections
Radiation source: fine-focus sealed tube	4661 reflections with I > 2σ(I)
graphite	Rint = 0.057
φ and ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −23→27
Tmin = 0.636, Tmax = 0.987	k = −15→14
28181 measured reflections	l = −13→13

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0891P)2 + 0.9992P] where P = (Fo2 + 2Fc2)/3
6088 reflections	(Δ/σ)max = 0.001
349 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.54 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	0.36811 (2)	0.64135 (4)	−0.09053 (5)	0.02080 (15)
O1	0.39510 (7)	0.60291 (13)	−0.19725 (13)	0.0264 (3)
O2	0.36734 (7)	0.76149 (12)	−0.06064 (14)	0.0266 (3)
O3	0.07988 (7)	0.14332 (12)	0.25445 (14)	0.0235 (3)
N1	0.29441 (8)	0.59952 (14)	−0.11262 (15)	0.0197 (4)
N2	0.18416 (8)	0.55576 (14)	0.11176 (16)	0.0202 (4)
H1N2	0.1626 (11)	0.619 (2)	0.122 (2)	0.024 (6)*
C1	0.28306 (10)	0.47333 (16)	−0.12239 (18)	0.0195 (4)
H1A	0.3222	0.4312	−0.1194	0.023*
H1B	0.2557	0.4539	−0.1991	0.023*
C2	0.25163 (9)	0.44865 (15)	−0.00752 (17)	0.0172 (4)
H2	0.2834	0.4530	0.0673	0.021*
C3	0.21612 (9)	0.33569 (15)	−0.00428 (17)	0.0169 (4)
H3	0.1899	0.3268	−0.0860	0.020*
C4	0.17183 (9)	0.34490 (16)	0.09480 (17)	0.0176 (4)
C5	0.14457 (9)	0.24516 (16)	0.13452 (18)	0.0182 (4)
H5	0.1546	0.1747	0.1016	0.022*
C6	0.10267 (9)	0.24795 (16)	0.22227 (18)	0.0194 (4)
C7	0.08772 (10)	0.35345 (17)	0.27171 (19)	0.0213 (4)
H7	0.0602	0.3569	0.3308	0.026*
C8	0.11424 (10)	0.45329 (17)	0.23202 (19)	0.0213 (4)
H8	0.1037	0.5236	0.2648	0.026*
C9	0.15627 (9)	0.45154 (16)	0.14423 (18)	0.0181 (4)
C10	0.20811 (9)	0.55138 (16)	−0.00791 (18)	0.0179 (4)
H10	0.1731	0.5435	−0.0764	0.022*
C11	0.24967 (10)	0.65334 (16)	−0.03459 (18)	0.0192 (4)
H11	0.2727	0.6828	0.0441	0.023*
C12	0.40517 (9)	0.56541 (17)	0.04217 (18)	0.0206 (4)
C13	0.40440 (10)	0.60984 (18)	0.16170 (19)	0.0231 (4)
H13	0.3878	0.6825	0.1723	0.028*
C14	0.42880 (10)	0.54439 (18)	0.2653 (2)	0.0249 (5)
H14	0.4288	0.5744	0.3454	0.030*
C15	0.45327 (10)	0.43488 (19)	0.2518 (2)	0.0251 (5)
C16	0.45382 (10)	0.39268 (18)	0.1305 (2)	0.0238 (4)
H16	0.4702	0.3199	0.1197	0.029*
C17	0.43044 (10)	0.45702 (17)	0.0261 (2)	0.0233 (4)
H17	0.4316	0.4281	−0.0541	0.028*
C18	0.47876 (12)	0.3636 (2)	0.3642 (2)	0.0334 (5)
H18A	0.4656	0.3963	0.4382	0.050*
H18B	0.5238	0.3627	0.3732	0.050*
H18C	0.4631	0.2864	0.3531	0.050*
C19	0.26098 (9)	0.23397 (16)	0.01226 (18)	0.0177 (4)
C20	0.30745 (10)	0.22449 (17)	0.11657 (19)	0.0220 (4)
H20	0.3105	0.2803	0.1791	0.026*
C21	0.34910 (10)	0.13259 (18)	0.1278 (2)	0.0254 (5)
H21	0.3800	0.1277	0.1974	0.030*
C22	0.34495 (11)	0.04784 (17)	0.0358 (2)	0.0268 (5)
H22	0.3725	−0.0143	0.0441	0.032*
C23	0.29953 (11)	0.05698 (17)	−0.0680 (2)	0.0269 (5)
H23	0.2968	0.0013	−0.1306	0.032*
C24	0.25761 (10)	0.14916 (17)	−0.0797 (2)	0.0223 (4)
H24	0.2270	0.1540	−0.1499	0.027*
C25	0.21481 (10)	0.75164 (17)	−0.10939 (19)	0.0227 (4)
H25A	0.2447	0.8112	−0.1230	0.027*
H25B	0.1962	0.7229	−0.1909	0.027*
C26	0.16400 (10)	0.80340 (16)	−0.04408 (18)	0.0202 (4)
C27	0.10099 (10)	0.77711 (17)	−0.0814 (2)	0.0249 (5)
H27	0.0900	0.7246	−0.1461	0.030*
C28	0.05413 (11)	0.82820 (19)	−0.0235 (2)	0.0276 (5)
H28	0.0122	0.8108	−0.0503	0.033*
C29	0.07005 (11)	0.90497 (18)	0.0741 (2)	0.0275 (5)
H29	0.0388	0.9400	0.1124	0.033*
C30	0.13279 (10)	0.92955 (17)	0.1147 (2)	0.0237 (4)
H30	0.1437	0.9797	0.1817	0.028*
C31	0.17939 (10)	0.87961 (16)	0.05583 (19)	0.0213 (4)
H31	0.2213	0.8971	0.0832	0.026*
C32	0.03712 (10)	0.14275 (18)	0.3447 (2)	0.0255 (5)
H32A	0.0236	0.0653	0.3568	0.038*
H32B	0.0014	0.1897	0.3150	0.038*
H32C	0.0577	0.1728	0.4230	0.038*

	U11	U22	U33	U12	U13	U23
S1	0.0206 (3)	0.0180 (3)	0.0242 (3)	−0.00236 (19)	0.0046 (2)	0.00132 (18)
O1	0.0265 (9)	0.0282 (8)	0.0259 (8)	−0.0026 (6)	0.0091 (6)	0.0015 (6)
O2	0.0252 (9)	0.0192 (7)	0.0353 (8)	−0.0044 (6)	0.0042 (7)	0.0022 (6)
O3	0.0211 (8)	0.0197 (7)	0.0313 (8)	−0.0037 (6)	0.0089 (6)	−0.0016 (6)
N1	0.0190 (9)	0.0161 (8)	0.0245 (9)	0.0001 (7)	0.0044 (7)	0.0006 (6)
N2	0.0250 (10)	0.0124 (8)	0.0243 (9)	0.0029 (7)	0.0075 (7)	−0.0008 (6)
C1	0.0199 (11)	0.0162 (9)	0.0222 (10)	0.0009 (7)	0.0029 (8)	−0.0006 (7)
C2	0.0164 (10)	0.0145 (9)	0.0204 (9)	0.0006 (7)	0.0014 (8)	−0.0007 (7)
C3	0.0156 (10)	0.0159 (9)	0.0189 (9)	0.0004 (7)	0.0015 (7)	−0.0002 (7)
C4	0.0150 (10)	0.0182 (9)	0.0188 (9)	0.0020 (7)	−0.0007 (7)	−0.0015 (7)
C5	0.0161 (10)	0.0155 (9)	0.0223 (10)	0.0012 (7)	0.0008 (8)	−0.0015 (7)
C6	0.0154 (10)	0.0179 (9)	0.0242 (10)	−0.0018 (7)	0.0007 (8)	0.0005 (7)
C7	0.0158 (10)	0.0246 (10)	0.0245 (10)	0.0012 (8)	0.0056 (8)	−0.0012 (8)
C8	0.0189 (11)	0.0180 (10)	0.0270 (10)	0.0039 (8)	0.0030 (8)	−0.0035 (8)
C9	0.0144 (10)	0.0169 (9)	0.0222 (10)	0.0002 (7)	−0.0009 (8)	−0.0010 (7)
C10	0.0182 (10)	0.0163 (9)	0.0190 (9)	0.0006 (7)	0.0017 (8)	−0.0003 (7)
C11	0.0196 (11)	0.0159 (9)	0.0224 (10)	0.0010 (7)	0.0038 (8)	−0.0009 (7)
C12	0.0152 (10)	0.0221 (10)	0.0248 (10)	−0.0020 (8)	0.0038 (8)	0.0008 (8)
C13	0.0208 (11)	0.0205 (10)	0.0282 (11)	−0.0011 (8)	0.0045 (8)	−0.0022 (8)
C14	0.0212 (11)	0.0296 (11)	0.0239 (10)	−0.0007 (9)	0.0035 (8)	−0.0036 (8)
C15	0.0151 (11)	0.0296 (11)	0.0301 (11)	−0.0011 (8)	0.0022 (8)	0.0031 (9)
C16	0.0151 (10)	0.0226 (10)	0.0336 (11)	0.0003 (8)	0.0035 (8)	−0.0014 (8)
C17	0.0205 (11)	0.0236 (10)	0.0266 (11)	−0.0016 (8)	0.0058 (8)	−0.0043 (8)
C18	0.0320 (14)	0.0355 (13)	0.0325 (12)	0.0057 (10)	0.0036 (10)	0.0063 (10)
C19	0.0160 (10)	0.0147 (9)	0.0235 (10)	−0.0002 (7)	0.0068 (8)	0.0028 (7)
C20	0.0225 (11)	0.0212 (10)	0.0228 (10)	0.0027 (8)	0.0046 (8)	0.0006 (8)
C21	0.0212 (11)	0.0280 (11)	0.0277 (11)	0.0056 (9)	0.0058 (9)	0.0086 (8)
C22	0.0267 (12)	0.0169 (10)	0.0399 (12)	0.0061 (8)	0.0152 (10)	0.0061 (8)
C23	0.0274 (12)	0.0169 (10)	0.0386 (12)	−0.0010 (8)	0.0127 (10)	−0.0058 (9)
C24	0.0199 (11)	0.0197 (10)	0.0277 (11)	−0.0021 (8)	0.0047 (8)	−0.0026 (8)
C25	0.0269 (12)	0.0178 (10)	0.0237 (10)	0.0034 (8)	0.0044 (9)	0.0038 (8)
C26	0.0241 (11)	0.0126 (9)	0.0238 (10)	0.0023 (7)	0.0032 (8)	0.0059 (7)
C27	0.0287 (12)	0.0176 (9)	0.0271 (11)	−0.0024 (8)	−0.0006 (9)	0.0027 (8)
C28	0.0189 (11)	0.0301 (11)	0.0331 (12)	−0.0022 (9)	0.0011 (9)	0.0079 (9)
C29	0.0248 (12)	0.0253 (11)	0.0342 (12)	0.0049 (9)	0.0099 (9)	0.0075 (9)
C30	0.0280 (12)	0.0173 (9)	0.0264 (10)	0.0005 (8)	0.0057 (9)	0.0021 (8)
C31	0.0193 (11)	0.0158 (9)	0.0282 (11)	0.0005 (8)	0.0015 (8)	0.0038 (8)
C32	0.0210 (11)	0.0261 (11)	0.0307 (11)	−0.0041 (8)	0.0080 (9)	0.0006 (9)

S1—O1	1.4303 (15)	C14—H14	0.93
S1—O2	1.4332 (15)	C15—C16	1.396 (3)
S1—N1	1.6424 (18)	C15—C18	1.504 (3)
S1—C12	1.768 (2)	C16—C17	1.383 (3)
O3—C6	1.374 (2)	C16—H16	0.93
O3—C32	1.430 (2)	C17—H17	0.93
N1—C1	1.488 (2)	C18—H18A	0.96
N1—C11	1.501 (2)	C18—H18B	0.96
N2—C9	1.417 (2)	C18—H18C	0.96
N2—C10	1.455 (2)	C19—C24	1.391 (3)
N2—H1N2	0.88 (2)	C19—C20	1.396 (3)
C1—C2	1.519 (3)	C20—C21	1.388 (3)
C1—H1A	0.97	C20—H20	0.93
C1—H1B	0.97	C21—C22	1.390 (3)
C2—C10	1.516 (3)	C21—H21	0.93
C2—C3	1.521 (3)	C22—C23	1.379 (3)
C2—H2	0.98	C22—H22	0.93
C3—C19	1.520 (3)	C23—C24	1.394 (3)
C3—C4	1.532 (3)	C23—H23	0.93
C3—H3	0.98	C24—H24	0.93
C4—C5	1.393 (3)	C25—C26	1.506 (3)
C4—C9	1.407 (3)	C25—H25A	0.97
C5—C6	1.396 (3)	C25—H25B	0.97
C5—H5	0.93	C26—C27	1.391 (3)
C6—C7	1.392 (3)	C26—C31	1.396 (3)
C7—C8	1.387 (3)	C27—C28	1.392 (3)
C7—H7	0.93	C27—H27	0.93
C8—C9	1.398 (3)	C28—C29	1.383 (3)
C8—H8	0.93	C28—H28	0.93
C10—C11	1.536 (3)	C29—C30	1.387 (3)
C10—H10	0.98	C29—H29	0.93
C11—C25	1.530 (3)	C30—C31	1.387 (3)
C11—H11	0.98	C30—H30	0.93
C12—C13	1.388 (3)	C31—H31	0.93
C12—C17	1.392 (3)	C32—H32A	0.96
C13—C14	1.389 (3)	C32—H32B	0.96
C13—H13	0.93	C32—H32C	0.96
C14—C15	1.392 (3)
O1—S1—O2	120.22 (9)	C13—C14—C15	121.46 (19)
O1—S1—N1	106.58 (9)	C13—C14—H14	119.3
O2—S1—N1	106.18 (9)	C15—C14—H14	119.3
O1—S1—C12	107.76 (9)	C14—C15—C16	118.19 (19)
O2—S1—C12	108.85 (9)	C14—C15—C18	121.25 (19)
N1—S1—C12	106.47 (9)	C16—C15—C18	120.6 (2)
C6—O3—C32	117.56 (15)	C17—C16—C15	121.27 (19)
C1—N1—C11	109.76 (15)	C17—C16—H16	119.4
C1—N1—S1	116.56 (13)	C15—C16—H16	119.4
C11—N1—S1	118.58 (13)	C16—C17—C12	119.42 (19)
C9—N2—C10	113.85 (15)	C16—C17—H17	120.3
C9—N2—H1N2	115.6 (15)	C12—C17—H17	120.3
C10—N2—H1N2	113.5 (15)	C15—C18—H18A	109.5
N1—C1—C2	102.50 (15)	C15—C18—H18B	109.5
N1—C1—H1A	111.3	H18A—C18—H18B	109.5
C2—C1—H1A	111.3	C15—C18—H18C	109.5
N1—C1—H1B	111.3	H18A—C18—H18C	109.5
C2—C1—H1B	111.3	H18B—C18—H18C	109.5
H1A—C1—H1B	109.2	C24—C19—C20	118.32 (18)
C10—C2—C1	101.27 (15)	C24—C19—C3	120.00 (18)
C10—C2—C3	111.56 (16)	C20—C19—C3	121.65 (17)
C1—C2—C3	117.70 (15)	C21—C20—C19	120.63 (19)
C10—C2—H2	108.6	C21—C20—H20	119.7
C1—C2—H2	108.6	C19—C20—H20	119.7
C3—C2—H2	108.6	C20—C21—C22	120.5 (2)
C19—C3—C2	111.18 (16)	C20—C21—H21	119.7
C19—C3—C4	114.85 (15)	C22—C21—H21	119.7
C2—C3—C4	108.65 (15)	C23—C22—C21	119.24 (19)
C19—C3—H3	107.3	C23—C22—H22	120.4
C2—C3—H3	107.3	C21—C22—H22	120.4
C4—C3—H3	107.3	C22—C23—C24	120.41 (19)
C5—C4—C9	118.88 (18)	C22—C23—H23	119.8
C5—C4—C3	119.10 (16)	C24—C23—H23	119.8
C9—C4—C3	121.99 (17)	C19—C24—C23	120.9 (2)
C4—C5—C6	121.94 (17)	C19—C24—H24	119.6
C4—C5—H5	119.0	C23—C24—H24	119.6
C6—C5—H5	119.0	C26—C25—C11	112.71 (16)
O3—C6—C7	124.94 (18)	C26—C25—H25A	109.1
O3—C6—C5	115.99 (17)	C11—C25—H25A	109.1
C7—C6—C5	119.07 (18)	C26—C25—H25B	109.1
C8—C7—C6	119.42 (18)	C11—C25—H25B	109.1
C8—C7—H7	120.3	H25A—C25—H25B	107.8
C6—C7—H7	120.3	C27—C26—C31	118.40 (19)
C7—C8—C9	122.02 (18)	C27—C26—C25	121.28 (19)
C7—C8—H8	119.0	C31—C26—C25	120.32 (19)
C9—C8—H8	119.0	C26—C27—C28	121.0 (2)
C8—C9—C4	118.68 (17)	C26—C27—H27	119.5
C8—C9—N2	119.44 (17)	C28—C27—H27	119.5
C4—C9—N2	121.81 (17)	C29—C28—C27	119.9 (2)
N2—C10—C2	108.76 (15)	C29—C28—H28	120.0
N2—C10—C11	115.32 (16)	C27—C28—H28	120.0
C2—C10—C11	103.43 (16)	C28—C29—C30	119.7 (2)
N2—C10—H10	109.7	C28—C29—H29	120.1
C2—C10—H10	109.7	C30—C29—H29	120.1
C11—C10—H10	109.7	C31—C30—C29	120.2 (2)
N1—C11—C25	108.76 (15)	C31—C30—H30	119.9
N1—C11—C10	102.71 (14)	C29—C30—H30	119.9
C25—C11—C10	114.82 (17)	C30—C31—C26	120.7 (2)
N1—C11—H11	110.1	C30—C31—H31	119.7
C25—C11—H11	110.1	C26—C31—H31	119.7
C10—C11—H11	110.1	O3—C32—H32A	109.5
C13—C12—C17	120.53 (19)	O3—C32—H32B	109.5
C13—C12—S1	119.93 (16)	H32A—C32—H32B	109.5
C17—C12—S1	119.33 (15)	O3—C32—H32C	109.5
C12—C13—C14	119.12 (19)	H32A—C32—H32C	109.5
C12—C13—H13	120.4	H32B—C32—H32C	109.5
C14—C13—H13	120.4
O1—S1—N1—C1	61.38 (15)	N2—C10—C11—N1	148.55 (16)
O2—S1—N1—C1	−169.33 (13)	C2—C10—C11—N1	29.94 (19)
C12—S1—N1—C1	−53.44 (16)	N2—C10—C11—C25	−93.6 (2)
O1—S1—N1—C11	−163.96 (13)	C2—C10—C11—C25	147.81 (16)
O2—S1—N1—C11	−34.67 (16)	O1—S1—C12—C13	158.49 (16)
C12—S1—N1—C11	81.22 (15)	O2—S1—C12—C13	26.59 (19)
C11—N1—C1—C2	−23.1 (2)	N1—S1—C12—C13	−87.49 (18)
S1—N1—C1—C2	115.35 (15)	O1—S1—C12—C17	−26.68 (19)
N1—C1—C2—C10	40.98 (18)	O2—S1—C12—C17	−158.58 (16)
N1—C1—C2—C3	162.85 (16)	N1—S1—C12—C17	87.34 (18)
C10—C2—C3—C19	−173.02 (15)	C17—C12—C13—C14	−0.4 (3)
C1—C2—C3—C19	70.6 (2)	S1—C12—C13—C14	174.34 (16)
C10—C2—C3—C4	−45.7 (2)	C12—C13—C14—C15	−0.8 (3)
C1—C2—C3—C4	−162.10 (16)	C13—C14—C15—C16	1.2 (3)
C19—C3—C4—C5	−40.9 (2)	C13—C14—C15—C18	−179.1 (2)
C2—C3—C4—C5	−166.12 (17)	C14—C15—C16—C17	−0.4 (3)
C19—C3—C4—C9	141.09 (18)	C18—C15—C16—C17	179.9 (2)
C2—C3—C4—C9	15.9 (2)	C15—C16—C17—C12	−0.8 (3)
C9—C4—C5—C6	−0.4 (3)	C13—C12—C17—C16	1.2 (3)
C3—C4—C5—C6	−178.46 (18)	S1—C12—C17—C16	−173.61 (16)
C32—O3—C6—C7	0.6 (3)	C2—C3—C19—C24	−118.83 (19)
C32—O3—C6—C5	179.61 (18)	C4—C3—C19—C24	117.29 (19)
C4—C5—C6—O3	−179.17 (17)	C2—C3—C19—C20	59.2 (2)
C4—C5—C6—C7	−0.1 (3)	C4—C3—C19—C20	−64.7 (2)
O3—C6—C7—C8	179.58 (19)	C24—C19—C20—C21	0.0 (3)
C5—C6—C7—C8	0.6 (3)	C3—C19—C20—C21	−178.04 (18)
C6—C7—C8—C9	−0.6 (3)	C19—C20—C21—C22	−0.5 (3)
C7—C8—C9—C4	0.1 (3)	C20—C21—C22—C23	1.0 (3)
C7—C8—C9—N2	−177.01 (19)	C21—C22—C23—C24	−1.0 (3)
C5—C4—C9—C8	0.4 (3)	C20—C19—C24—C23	0.0 (3)
C3—C4—C9—C8	178.37 (17)	C3—C19—C24—C23	178.09 (18)
C5—C4—C9—N2	177.43 (18)	C22—C23—C24—C19	0.5 (3)
C3—C4—C9—N2	−4.6 (3)	N1—C11—C25—C26	174.16 (16)
C10—N2—C9—C8	−159.30 (18)	C10—C11—C25—C26	59.8 (2)
C10—N2—C9—C4	23.6 (3)	C11—C25—C26—C27	−102.6 (2)
C9—N2—C10—C2	−53.1 (2)	C11—C25—C26—C31	77.6 (2)
C9—N2—C10—C11	−168.66 (16)	C31—C26—C27—C28	2.0 (3)
C1—C2—C10—N2	−167.42 (15)	C25—C26—C27—C28	−177.81 (18)
C3—C2—C10—N2	66.5 (2)	C26—C27—C28—C29	−1.1 (3)
C1—C2—C10—C11	−44.36 (18)	C27—C28—C29—C30	−0.8 (3)
C3—C2—C10—C11	−170.41 (15)	C28—C29—C30—C31	1.6 (3)
C1—N1—C11—C25	−126.22 (17)	C29—C30—C31—C26	−0.5 (3)
S1—N1—C11—C25	96.32 (18)	C27—C26—C31—C30	−1.2 (3)
C1—N1—C11—C10	−4.1 (2)	C25—C26—C31—C30	178.62 (18)
S1—N1—C11—C10	−141.61 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C30—H30···O3i	0.93	2.53	3.196 (3)	128
C24—H24···Cg1ii	0.93	2.56	3.476 (2)	169
N2—H1N2···Cg2	0.88 (2)	3.06	3.837 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C30—H30⋯O3i	0.93	2.53	3.196 (3)	128
C24—H24⋯Cg1ii	0.93	2.56	3.476 (2)	169
N2—H1N2⋯Cg2	0.88 (2)	3.06	3.837 (2)	147

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