3-Benzyl-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(30)N(2)O(2)S, the pyrrolidine ring adopts a twist conformation while the tetra-hydro-pyridine ring is in a half-chair conformation. The two rings are trans-fused. The pyridine-bound phenyl ring forms dihedral angles of 17.7 (1) and 48.1 (1)°, respectively, with the tosyl and benzyl phenyl rings. The mol-ecular structure is stabilized by an N-H⋯π inter-action involving the benzyl phenyl ring. In the crystal structure, mol-ecules translated by one unit along the a axis are linked into chains by C-H⋯π inter-actions involving the benzene ring of the tosyl group.

Related literature

For the biological activity of pyrroloquinoline derivatives, see: Ferlin et al. (2005 ▶); Dalla Via et al. (2008 ▶); Xiao et al. (2006 ▶); Fujita et al. (1996 ▶); Crenshaw et al. (1976 ▶). For the crystal structure of the 3-ethyl analogue, see: Sudha et al. (2008 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Duax et al. (1976 ▶).

Experimental

Crystal data

C31H30N2O2S

M = 494.63

Triclinic,

a = 10.9521 (3) Å

b = 11.2563 (3) Å

c = 12.5132 (3) Å

α = 100.930 (2)°

β = 108.577 (1)°

γ = 114.539 (1)°

V = 1234.00 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.16 mm−1

T = 100 K

0.48 × 0.24 × 0.23 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.761, T max = 0.963

27773 measured reflections

6486 independent reflections

5001 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.112

S = 1.01

6486 reflections

330 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.51 e Å−3

Δρmin = −0.42 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/S1600536809044547/wn2361sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044547/wn2361Isup2.hkl

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

C31H30N2O2S	Z = 2
Mr = 494.63	F(000) = 524
Triclinic, P1	Dx = 1.331 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.9521 (3) Å	Cell parameters from 9232 reflections
b = 11.2563 (3) Å	θ = 2.3–30.0°
c = 12.5132 (3) Å	µ = 0.16 mm−1
α = 100.930 (2)°	T = 100 K
β = 108.577 (1)°	Block, colourless
γ = 114.539 (1)°	0.48 × 0.24 × 0.23 mm
V = 1234.00 (6) Å3

Bruker SMART APEXII CCD area-detector diffractometer	6486 independent reflections
Radiation source: fine-focus sealed tube	5001 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 29.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→14
Tmin = 0.761, Tmax = 0.963	k = −15→15
27773 measured reflections	l = −17→17

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.046P)2 + 0.7475P] where P = (Fo2 + 2Fc2)/3
6486 reflections	(Δ/σ)max = 0.001
330 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.42 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	0.36310 (4)	0.70596 (4)	−0.01644 (4)	0.01857 (10)
O1	0.25363 (13)	0.74003 (13)	−0.07610 (11)	0.0250 (3)
O2	0.40078 (13)	0.62325 (12)	−0.08784 (10)	0.0240 (3)
N1	0.51710 (14)	0.85539 (13)	0.07238 (12)	0.0173 (3)
N2	0.87750 (15)	1.02866 (14)	0.33742 (12)	0.0179 (3)
H1N2	0.939 (2)	1.009 (2)	0.3253 (18)	0.026 (5)*
C1	0.50851 (17)	0.96845 (16)	0.14938 (14)	0.0181 (3)
H1A	0.4181	0.9292	0.1604	0.022*
H1B	0.5109	1.0381	0.1136	0.022*
C2	0.64811 (17)	1.03222 (15)	0.26952 (14)	0.0150 (3)
H2	0.6244	0.9770	0.3194	0.018*
C3	0.72246 (17)	1.18825 (15)	0.34620 (14)	0.0151 (3)
H3	0.7343	1.2408	0.2925	0.018*
C4	0.87963 (17)	1.23749 (16)	0.44241 (14)	0.0158 (3)
C5	0.95793 (18)	1.36418 (16)	0.54193 (15)	0.0185 (3)
H5	0.9122	1.4167	0.5496	0.022*
C6	1.10111 (18)	1.41433 (17)	0.62954 (15)	0.0210 (3)
H6	1.1509	1.4995	0.6945	0.025*
C7	1.16958 (18)	1.33567 (17)	0.61916 (15)	0.0215 (3)
H7	1.2659	1.3683	0.6774	0.026*
C8	1.09513 (18)	1.20931 (17)	0.52270 (15)	0.0194 (3)
H8	1.1414	1.1570	0.5169	0.023*
C9	0.95044 (17)	1.15885 (16)	0.43336 (14)	0.0165 (3)
C10	0.75726 (17)	1.00918 (16)	0.23056 (14)	0.0156 (3)
H10	0.7982	1.0779	0.1954	0.019*
C11	0.66205 (17)	0.86091 (16)	0.13260 (14)	0.0171 (3)
H11	0.6487	0.7906	0.1703	0.021*
C12	0.30055 (17)	0.61554 (16)	0.07342 (14)	0.0183 (3)
C13	0.35945 (18)	0.53371 (16)	0.11236 (15)	0.0207 (3)
H13	0.4332	0.5291	0.0933	0.025*
C14	0.30604 (19)	0.45969 (17)	0.17978 (15)	0.0218 (3)
H14	0.3452	0.4057	0.2060	0.026*
C15	0.19503 (18)	0.46425 (16)	0.20920 (15)	0.0202 (3)
C16	0.13799 (18)	0.54575 (17)	0.16856 (15)	0.0217 (3)
H16	0.0632	0.5492	0.1866	0.026*
C17	0.19011 (18)	0.62183 (16)	0.10184 (15)	0.0208 (3)
H17	0.1515	0.6765	0.0764	0.025*
C18	0.1399 (2)	0.38679 (18)	0.28517 (17)	0.0254 (4)
H18A	0.0355	0.3553	0.2593	0.038*
H18B	0.1958	0.4487	0.3691	0.038*
H18C	0.1533	0.3070	0.2755	0.038*
C19	0.63082 (17)	1.21998 (16)	0.40329 (14)	0.0164 (3)
C20	0.61254 (18)	1.17490 (17)	0.49677 (15)	0.0205 (3)
H20	0.6525	1.1206	0.5211	0.025*
C21	0.53582 (19)	1.20987 (18)	0.55365 (16)	0.0254 (4)
H21	0.5250	1.1796	0.6160	0.031*
C22	0.47489 (19)	1.29029 (18)	0.51758 (17)	0.0270 (4)
H22	0.4227	1.3134	0.5553	0.032*
C23	0.49216 (19)	1.33563 (18)	0.42575 (16)	0.0248 (4)
H23	0.4523	1.3902	0.4021	0.030*
C24	0.56895 (18)	1.30027 (16)	0.36793 (15)	0.0200 (3)
H24	0.5789	1.3305	0.3054	0.024*
C25	0.72722 (18)	0.83906 (18)	0.04379 (15)	0.0213 (3)
H25A	0.6672	0.7416	−0.0120	0.026*
H25B	0.7235	0.8977	−0.0034	0.026*
C26	0.88731 (18)	0.87601 (17)	0.11140 (14)	0.0193 (3)
C27	1.00564 (19)	1.00373 (17)	0.12935 (15)	0.0219 (3)
H27	0.9855	1.0633	0.0942	0.026*
C28	1.1526 (2)	1.04302 (18)	0.19876 (16)	0.0251 (4)
H28	1.2304	1.1272	0.2077	0.030*
C29	1.18447 (19)	0.95779 (19)	0.25491 (16)	0.0262 (4)
H29	1.2833	0.9853	0.3030	0.031*
C30	1.0679 (2)	0.83100 (19)	0.23886 (17)	0.0259 (4)
H30	1.0886	0.7739	0.2773	0.031*
C31	0.92062 (19)	0.78886 (17)	0.16586 (16)	0.0226 (4)
H31	0.8434	0.7019	0.1531	0.027*

	U11	U22	U33	U12	U13	U23
S1	0.01624 (19)	0.01639 (19)	0.01461 (19)	0.00506 (15)	0.00412 (15)	0.00178 (14)
O1	0.0177 (6)	0.0274 (6)	0.0207 (6)	0.0083 (5)	0.0026 (5)	0.0090 (5)
O2	0.0232 (6)	0.0204 (6)	0.0171 (6)	0.0060 (5)	0.0082 (5)	−0.0016 (5)
N1	0.0150 (6)	0.0137 (6)	0.0176 (7)	0.0066 (5)	0.0048 (5)	0.0009 (5)
N2	0.0174 (7)	0.0189 (7)	0.0163 (7)	0.0124 (6)	0.0047 (5)	0.0017 (5)
C1	0.0167 (7)	0.0165 (7)	0.0197 (8)	0.0095 (6)	0.0072 (6)	0.0033 (6)
C2	0.0156 (7)	0.0141 (7)	0.0158 (7)	0.0083 (6)	0.0074 (6)	0.0043 (6)
C3	0.0156 (7)	0.0134 (7)	0.0160 (7)	0.0076 (6)	0.0070 (6)	0.0042 (6)
C4	0.0149 (7)	0.0154 (7)	0.0166 (7)	0.0069 (6)	0.0077 (6)	0.0053 (6)
C5	0.0200 (8)	0.0152 (7)	0.0207 (8)	0.0091 (6)	0.0106 (6)	0.0046 (6)
C6	0.0179 (8)	0.0163 (7)	0.0188 (8)	0.0042 (6)	0.0062 (6)	0.0012 (6)
C7	0.0146 (7)	0.0235 (8)	0.0186 (8)	0.0064 (6)	0.0052 (6)	0.0042 (7)
C8	0.0178 (8)	0.0227 (8)	0.0206 (8)	0.0129 (7)	0.0088 (6)	0.0074 (7)
C9	0.0172 (7)	0.0164 (7)	0.0158 (7)	0.0081 (6)	0.0085 (6)	0.0048 (6)
C10	0.0157 (7)	0.0144 (7)	0.0154 (7)	0.0078 (6)	0.0064 (6)	0.0035 (6)
C11	0.0153 (7)	0.0154 (7)	0.0164 (7)	0.0074 (6)	0.0049 (6)	0.0022 (6)
C12	0.0179 (8)	0.0135 (7)	0.0148 (7)	0.0045 (6)	0.0047 (6)	0.0011 (6)
C13	0.0203 (8)	0.0175 (7)	0.0209 (8)	0.0094 (7)	0.0091 (7)	0.0016 (6)
C14	0.0270 (9)	0.0176 (7)	0.0226 (8)	0.0135 (7)	0.0112 (7)	0.0055 (6)
C15	0.0212 (8)	0.0136 (7)	0.0184 (8)	0.0059 (6)	0.0071 (6)	0.0013 (6)
C16	0.0182 (8)	0.0198 (8)	0.0246 (9)	0.0089 (7)	0.0097 (7)	0.0052 (7)
C17	0.0182 (8)	0.0163 (7)	0.0229 (8)	0.0082 (6)	0.0063 (7)	0.0042 (6)
C18	0.0301 (9)	0.0217 (8)	0.0292 (9)	0.0142 (7)	0.0165 (8)	0.0109 (7)
C19	0.0138 (7)	0.0133 (7)	0.0163 (7)	0.0050 (6)	0.0056 (6)	0.0012 (6)
C20	0.0201 (8)	0.0176 (7)	0.0220 (8)	0.0088 (6)	0.0096 (7)	0.0058 (6)
C21	0.0212 (8)	0.0238 (8)	0.0224 (9)	0.0050 (7)	0.0119 (7)	0.0029 (7)
C22	0.0177 (8)	0.0249 (9)	0.0282 (9)	0.0077 (7)	0.0109 (7)	−0.0037 (7)
C23	0.0201 (8)	0.0224 (8)	0.0289 (9)	0.0138 (7)	0.0081 (7)	0.0016 (7)
C24	0.0185 (8)	0.0165 (7)	0.0203 (8)	0.0086 (6)	0.0062 (6)	0.0030 (6)
C25	0.0215 (8)	0.0218 (8)	0.0173 (8)	0.0116 (7)	0.0073 (7)	0.0018 (6)
C26	0.0212 (8)	0.0201 (8)	0.0157 (7)	0.0120 (7)	0.0090 (6)	0.0002 (6)
C27	0.0253 (8)	0.0210 (8)	0.0200 (8)	0.0126 (7)	0.0113 (7)	0.0053 (7)
C28	0.0229 (8)	0.0221 (8)	0.0231 (9)	0.0070 (7)	0.0118 (7)	0.0024 (7)
C29	0.0191 (8)	0.0304 (9)	0.0229 (9)	0.0123 (7)	0.0075 (7)	0.0019 (7)
C30	0.0296 (9)	0.0260 (9)	0.0277 (9)	0.0198 (8)	0.0124 (8)	0.0082 (7)
C31	0.0243 (8)	0.0183 (8)	0.0245 (9)	0.0114 (7)	0.0124 (7)	0.0030 (7)

S1—O1	1.4360 (12)	C14—C15	1.395 (2)
S1—O2	1.4401 (12)	C14—H14	0.93
S1—N1	1.6277 (13)	C15—C16	1.393 (2)
S1—C12	1.7649 (17)	C15—C18	1.507 (2)
N1—C11	1.4934 (19)	C16—C17	1.387 (2)
N1—C1	1.4996 (19)	C16—H16	0.93
N2—C9	1.406 (2)	C17—H17	0.93
N2—C10	1.448 (2)	C18—H18A	0.96
N2—H1N2	0.83 (2)	C18—H18B	0.96
C1—C2	1.526 (2)	C18—H18C	0.96
C1—H1A	0.97	C19—C24	1.393 (2)
C1—H1B	0.97	C19—C20	1.399 (2)
C2—C10	1.521 (2)	C20—C21	1.385 (2)
C2—C3	1.531 (2)	C20—H20	0.93
C2—H2	0.98	C21—C22	1.390 (3)
C3—C19	1.518 (2)	C21—H21	0.93
C3—C4	1.534 (2)	C22—C23	1.377 (3)
C3—H3	0.98	C22—H22	0.93
C4—C5	1.397 (2)	C23—C24	1.395 (2)
C4—C9	1.409 (2)	C23—H23	0.93
C5—C6	1.384 (2)	C24—H24	0.93
C5—H5	0.93	C25—C26	1.510 (2)
C6—C7	1.390 (2)	C25—H25A	0.97
C6—H6	0.93	C25—H25B	0.97
C7—C8	1.380 (2)	C26—C27	1.393 (2)
C7—H7	0.93	C26—C31	1.397 (2)
C8—C9	1.402 (2)	C27—C28	1.383 (2)
C8—H8	0.93	C27—H27	0.93
C10—C11	1.530 (2)	C28—C29	1.383 (3)
C10—H10	0.98	C28—H28	0.93
C11—C25	1.534 (2)	C29—C30	1.386 (3)
C11—H11	0.98	C29—H29	0.93
C12—C17	1.389 (2)	C30—C31	1.387 (2)
C12—C13	1.402 (2)	C30—H30	0.93
C13—C14	1.387 (2)	C31—H31	0.93
C13—H13	0.93
O1—S1—O2	119.68 (7)	C14—C13—C12	118.98 (15)
O1—S1—N1	106.27 (7)	C14—C13—H13	120.5
O2—S1—N1	106.96 (7)	C12—C13—H13	120.5
O1—S1—C12	107.58 (8)	C13—C14—C15	121.68 (15)
O2—S1—C12	107.09 (7)	C13—C14—H14	119.2
N1—S1—C12	108.93 (7)	C15—C14—H14	119.2
C11—N1—C1	111.99 (12)	C16—C15—C14	118.02 (16)
C11—N1—S1	120.85 (10)	C16—C15—C18	120.34 (15)
C1—N1—S1	118.57 (10)	C14—C15—C18	121.62 (15)
C9—N2—C10	114.33 (12)	C17—C16—C15	121.59 (16)
C9—N2—H1N2	111.4 (14)	C17—C16—H16	119.2
C10—N2—H1N2	116.0 (14)	C15—C16—H16	119.2
N1—C1—C2	103.14 (12)	C16—C17—C12	119.40 (15)
N1—C1—H1A	111.1	C16—C17—H17	120.3
C2—C1—H1A	111.1	C12—C17—H17	120.3
N1—C1—H1B	111.1	C15—C18—H18A	109.5
C2—C1—H1B	111.1	C15—C18—H18B	109.5
H1A—C1—H1B	109.1	H18A—C18—H18B	109.5
C10—C2—C1	103.00 (12)	C15—C18—H18C	109.5
C10—C2—C3	109.13 (12)	H18A—C18—H18C	109.5
C1—C2—C3	118.14 (13)	H18B—C18—H18C	109.5
C10—C2—H2	108.7	C24—C19—C20	118.41 (15)
C1—C2—H2	108.7	C24—C19—C3	120.85 (14)
C3—C2—H2	108.7	C20—C19—C3	120.67 (14)
C19—C3—C2	113.47 (12)	C21—C20—C19	120.97 (16)
C19—C3—C4	111.61 (12)	C21—C20—H20	119.5
C2—C3—C4	108.54 (12)	C19—C20—H20	119.5
C19—C3—H3	107.7	C20—C21—C22	120.01 (17)
C2—C3—H3	107.7	C20—C21—H21	120.0
C4—C3—H3	107.7	C22—C21—H21	120.0
C5—C4—C9	117.86 (14)	C23—C22—C21	119.69 (16)
C5—C4—C3	120.29 (13)	C23—C22—H22	120.2
C9—C4—C3	121.85 (13)	C21—C22—H22	120.2
C6—C5—C4	122.35 (15)	C22—C23—C24	120.49 (16)
C6—C5—H5	118.8	C22—C23—H23	119.8
C4—C5—H5	118.8	C24—C23—H23	119.8
C5—C6—C7	119.10 (15)	C19—C24—C23	120.42 (16)
C5—C6—H6	120.4	C19—C24—H24	119.8
C7—C6—H6	120.4	C23—C24—H24	119.8
C8—C7—C6	120.19 (15)	C26—C25—C11	110.75 (13)
C8—C7—H7	119.9	C26—C25—H25A	109.5
C6—C7—H7	119.9	C11—C25—H25A	109.5
C7—C8—C9	120.77 (15)	C26—C25—H25B	109.5
C7—C8—H8	119.6	C11—C25—H25B	109.5
C9—C8—H8	119.6	H25A—C25—H25B	108.1
C8—C9—N2	119.04 (14)	C27—C26—C31	118.39 (15)
C8—C9—C4	119.73 (14)	C27—C26—C25	120.46 (15)
N2—C9—C4	121.22 (14)	C31—C26—C25	120.94 (15)
N2—C10—C2	107.97 (13)	C28—C27—C26	120.86 (16)
N2—C10—C11	115.04 (12)	C28—C27—H27	119.6
C2—C10—C11	104.70 (12)	C26—C27—H27	119.6
N2—C10—H10	109.6	C27—C28—C29	120.38 (16)
C2—C10—H10	109.6	C27—C28—H28	119.8
C11—C10—H10	109.6	C29—C28—H28	119.8
N1—C11—C10	100.91 (11)	C28—C29—C30	119.44 (16)
N1—C11—C25	112.14 (13)	C28—C29—H29	120.3
C10—C11—C25	113.02 (13)	C30—C29—H29	120.3
N1—C11—H11	110.2	C29—C30—C31	120.37 (17)
C10—C11—H11	110.2	C29—C30—H30	119.8
C25—C11—H11	110.2	C31—C30—H30	119.8
C17—C12—C13	120.33 (15)	C30—C31—C26	120.50 (16)
C17—C12—S1	120.10 (13)	C30—C31—H31	119.8
C13—C12—S1	119.54 (13)	C26—C31—H31	119.8
O1—S1—N1—C11	−169.30 (12)	N2—C10—C11—C25	−86.66 (17)
O2—S1—N1—C11	−40.37 (14)	C2—C10—C11—C25	155.01 (13)
C12—S1—N1—C11	75.06 (13)	O1—S1—C12—C17	−16.92 (15)
O1—S1—N1—C1	45.43 (13)	O2—S1—C12—C17	−146.77 (13)
O2—S1—N1—C1	174.35 (12)	N1—S1—C12—C17	97.88 (14)
C12—S1—N1—C1	−70.22 (13)	O1—S1—C12—C13	160.95 (12)
C11—N1—C1—C2	−7.78 (16)	O2—S1—C12—C13	31.10 (14)
S1—N1—C1—C2	140.39 (11)	N1—S1—C12—C13	−84.25 (13)
N1—C1—C2—C10	29.34 (15)	C17—C12—C13—C14	−0.2 (2)
N1—C1—C2—C3	149.66 (13)	S1—C12—C13—C14	−178.03 (12)
C10—C2—C3—C19	−172.66 (13)	C12—C13—C14—C15	0.3 (2)
C1—C2—C3—C19	70.25 (18)	C13—C14—C15—C16	0.1 (2)
C10—C2—C3—C4	−47.97 (16)	C13—C14—C15—C18	−178.40 (15)
C1—C2—C3—C4	−165.07 (13)	C14—C15—C16—C17	−0.7 (2)
C19—C3—C4—C5	−38.87 (19)	C18—C15—C16—C17	177.88 (15)
C2—C3—C4—C5	−164.65 (14)	C15—C16—C17—C12	0.8 (2)
C19—C3—C4—C9	141.90 (15)	C13—C12—C17—C16	−0.4 (2)
C2—C3—C4—C9	16.12 (19)	S1—C12—C17—C16	177.50 (12)
C9—C4—C5—C6	0.7 (2)	C2—C3—C19—C24	−113.47 (16)
C3—C4—C5—C6	−178.57 (15)	C4—C3—C19—C24	123.52 (15)
C4—C5—C6—C7	−0.5 (3)	C2—C3—C19—C20	69.60 (18)
C5—C6—C7—C8	−0.1 (3)	C4—C3—C19—C20	−53.42 (18)
C6—C7—C8—C9	0.6 (3)	C24—C19—C20—C21	−0.5 (2)
C7—C8—C9—N2	−179.10 (15)	C3—C19—C20—C21	176.54 (14)
C7—C8—C9—C4	−0.4 (2)	C19—C20—C21—C22	0.4 (2)
C10—N2—C9—C8	−159.03 (14)	C20—C21—C22—C23	−0.4 (3)
C10—N2—C9—C4	22.3 (2)	C21—C22—C23—C24	0.6 (3)
C5—C4—C9—C8	−0.2 (2)	C20—C19—C24—C23	0.7 (2)
C3—C4—C9—C8	179.05 (14)	C3—C19—C24—C23	−176.33 (14)
C5—C4—C9—N2	178.46 (15)	C22—C23—C24—C19	−0.8 (2)
C3—C4—C9—N2	−2.3 (2)	N1—C11—C25—C26	167.76 (13)
C9—N2—C10—C2	−55.04 (17)	C10—C11—C25—C26	54.52 (18)
C9—N2—C10—C11	−171.53 (13)	C11—C25—C26—C27	−102.25 (18)
C1—C2—C10—N2	−164.09 (12)	C11—C25—C26—C31	72.43 (19)
C3—C2—C10—N2	69.58 (15)	C31—C26—C27—C28	0.4 (2)
C1—C2—C10—C11	−41.05 (15)	C25—C26—C27—C28	175.20 (15)
C3—C2—C10—C11	−167.38 (12)	C26—C27—C28—C29	−2.0 (3)
C1—N1—C11—C10	−16.78 (16)	C27—C28—C29—C30	1.4 (3)
S1—N1—C11—C10	−164.12 (11)	C28—C29—C30—C31	0.9 (3)
C1—N1—C11—C25	−137.32 (14)	C29—C30—C31—C26	−2.5 (3)
S1—N1—C11—C25	75.33 (16)	C27—C26—C31—C30	1.9 (2)
N2—C10—C11—N1	153.42 (13)	C25—C26—C31—C30	−172.91 (15)
C2—C10—C11—N1	35.09 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···Cg2	0.83 (2)	2.61 (2)	3.374 (2)	152 (2)
C29—H29···Cg1i	0.93	2.90	3.605 (2)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯Cg2	0.83 (2)	2.61 (2)	3.374 (2)	152 (2)
C29—H29⋯Cg1i	0.93	2.90	3.605 (2)	134

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