7'-Phenyl-1',3',5',6',7',7a'-hexa-hydro-dipiro[acenaphthyl-ene-1,5'-pyrrolo-[1,2-c]thia-zole-6',2''-indane]-2,1''(1H)-dione.

In the title compound, C(31)H(23)NO(2)S, the pyrrolidine ring adopts an envelope conformation (with the spiro C atom as the flap), while the thia-zolidine ring and the two cyclo-pentane rings adopt twisted conformations. The mean plane through the hexa-hydro-pyrrolo-[1,2-c]thia-zole ring [r.m.s deviation = 0.400 (1) Å] forms dihedral angles of 76.83 (4), 80.70 (5) and 79.00 (4)° with the benzene ring and the mean planes of the dihydro-acenaphthyl-ene and the dihydro-indene rings, respectively. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds into sheets lying parallel to the bc plane. One of the ketone O atoms accepts three such bonds. Weak C-H⋯π inter-actions are also observed.

Related literature

For related structures, see: Wei et al. (2011a ▶,b ▶, 2012 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C31H23NO2S

M = 473.56

Monoclinic,

a = 8.4054 (1) Å

b = 11.3716 (1) Å

c = 23.5194 (2) Å

β = 92.259 (1)°

V = 2246.30 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 100 K

0.30 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.949, T max = 0.972

39597 measured reflections

10047 independent reflections

7694 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.124

S = 1.03

10047 reflections

316 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536812013293/hb6700sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013293/hb6700Isup2.hkl

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

C31H23NO2S	F(000) = 992
Mr = 473.56	Dx = 1.400 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9949 reflections
a = 8.4054 (1) Å	θ = 2.5–35.2°
b = 11.3716 (1) Å	µ = 0.18 mm−1
c = 23.5194 (2) Å	T = 100 K
β = 92.259 (1)°	Block, yellow
V = 2246.30 (4) Å3	0.30 × 0.18 × 0.16 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	10047 independent reflections
Radiation source: fine-focus sealed tube	7694 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 35.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.949, Tmax = 0.972	k = −18→14
39597 measured reflections	l = −38→28

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0523P)2 + 0.9508P] where P = (Fo2 + 2Fc2)/3
10047 reflections	(Δ/σ)max = 0.001
316 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.86000 (4)	0.42837 (3)	0.121701 (14)	0.01913 (7)
O1	0.48435 (10)	0.17004 (8)	0.24386 (3)	0.01480 (15)
O2	0.24182 (10)	0.24847 (8)	0.04159 (3)	0.01487 (16)
N1	0.60468 (11)	0.35224 (8)	0.17368 (4)	0.01107 (16)
C1	0.49807 (12)	0.15401 (9)	0.19309 (4)	0.01060 (17)
C2	0.51959 (12)	0.04064 (9)	0.16415 (4)	0.01095 (18)
C3	0.50561 (13)	−0.07416 (10)	0.18207 (5)	0.01361 (19)
H3A	0.4668	−0.0923	0.2184	0.016*
C4	0.55106 (14)	−0.16396 (10)	0.14435 (5)	0.0159 (2)
H4A	0.5401	−0.2437	0.1556	0.019*
C5	0.61100 (14)	−0.13945 (10)	0.09164 (5)	0.0153 (2)
H5A	0.6423	−0.2022	0.0679	0.018*
C6	0.62624 (13)	−0.02169 (10)	0.07274 (5)	0.01244 (18)
C7	0.68707 (13)	0.01653 (10)	0.02044 (5)	0.0147 (2)
H7A	0.7235	−0.0392	−0.0062	0.018*
C8	0.69293 (14)	0.13492 (10)	0.00849 (5)	0.0147 (2)
H8A	0.7345	0.1592	−0.0266	0.018*
C9	0.63933 (13)	0.22232 (10)	0.04655 (5)	0.01278 (18)
H9A	0.6441	0.3032	0.0367	0.015*
C10	0.58047 (12)	0.18838 (9)	0.09778 (4)	0.01008 (17)
C11	0.57568 (12)	0.06664 (9)	0.10990 (4)	0.01046 (17)
C12	0.51304 (12)	0.25553 (9)	0.14809 (4)	0.00966 (17)
C13	0.34938 (12)	0.32033 (9)	0.13396 (4)	0.00936 (17)
C14	0.25058 (12)	0.32869 (10)	0.18797 (4)	0.01128 (18)
H14A	0.3205	0.3309	0.2228	0.014*
H14B	0.1818	0.3994	0.1869	0.014*
C15	0.15252 (12)	0.21773 (10)	0.18530 (5)	0.01242 (18)
C16	0.07876 (14)	0.15873 (11)	0.22895 (5)	0.0173 (2)
H16A	0.0894	0.1859	0.2671	0.021*
C17	−0.01086 (15)	0.05901 (12)	0.21539 (6)	0.0217 (2)
H17A	−0.0608	0.0174	0.2448	0.026*
C18	−0.02897 (15)	0.01885 (12)	0.15930 (6)	0.0221 (2)
H18A	−0.0930	−0.0483	0.1510	0.027*
C19	0.04614 (14)	0.07663 (11)	0.11552 (6)	0.0176 (2)
H19A	0.0346	0.0501	0.0773	0.021*
C20	0.13885 (13)	0.17474 (10)	0.12972 (5)	0.01284 (18)
C21	0.24112 (12)	0.24687 (9)	0.09327 (4)	0.01074 (17)
C22	0.40993 (12)	0.43806 (9)	0.10995 (4)	0.01032 (17)
H22A	0.4528	0.4210	0.0717	0.012*
C23	0.55326 (12)	0.46704 (10)	0.15034 (5)	0.01232 (18)
H23A	0.5157	0.5170	0.1821	0.015*
C24	0.69479 (14)	0.52975 (11)	0.12283 (6)	0.0225 (3)
H24A	0.7256	0.6006	0.1451	0.027*
H24B	0.6638	0.5545	0.0836	0.027*
C25	0.77507 (13)	0.34147 (11)	0.17878 (5)	0.0159 (2)
H25A	0.8066	0.2580	0.1753	0.019*
H25B	0.8146	0.3710	0.2163	0.019*
C26	0.28586 (12)	0.53385 (9)	0.10170 (4)	0.01095 (17)
C27	0.20247 (13)	0.54334 (10)	0.04912 (5)	0.01402 (19)
H27A	0.2268	0.4909	0.0192	0.017*
C28	0.08491 (14)	0.62787 (11)	0.03980 (5)	0.0170 (2)
H28A	0.0287	0.6319	0.0040	0.020*
C29	0.04933 (14)	0.70648 (11)	0.08275 (5)	0.0176 (2)
H29A	−0.0311	0.7643	0.0765	0.021*
C30	0.13264 (14)	0.69968 (10)	0.13495 (5)	0.0163 (2)
H30A	0.1102	0.7540	0.1642	0.020*
C31	0.24880 (13)	0.61373 (10)	0.14462 (5)	0.01328 (19)
H31A	0.3035	0.6092	0.1807	0.016*

	U11	U22	U33	U12	U13	U23
S1	0.01378 (12)	0.01626 (14)	0.02775 (15)	−0.00203 (10)	0.00564 (10)	0.00049 (11)
O1	0.0201 (4)	0.0142 (4)	0.0101 (3)	0.0016 (3)	0.0005 (3)	0.0002 (3)
O2	0.0185 (4)	0.0146 (4)	0.0114 (3)	−0.0002 (3)	−0.0016 (3)	−0.0021 (3)
N1	0.0106 (4)	0.0089 (4)	0.0135 (4)	−0.0008 (3)	−0.0017 (3)	−0.0008 (3)
C1	0.0104 (4)	0.0104 (4)	0.0110 (4)	0.0011 (3)	−0.0002 (3)	0.0010 (3)
C2	0.0123 (4)	0.0094 (4)	0.0111 (4)	0.0004 (3)	−0.0002 (3)	0.0004 (3)
C3	0.0159 (4)	0.0113 (5)	0.0136 (4)	−0.0005 (4)	0.0000 (3)	0.0014 (4)
C4	0.0202 (5)	0.0095 (5)	0.0180 (5)	−0.0007 (4)	0.0002 (4)	0.0012 (4)
C5	0.0185 (5)	0.0104 (5)	0.0169 (5)	0.0005 (4)	0.0000 (4)	−0.0019 (4)
C6	0.0142 (4)	0.0098 (4)	0.0133 (4)	0.0003 (4)	0.0004 (3)	−0.0017 (3)
C7	0.0168 (5)	0.0139 (5)	0.0138 (4)	−0.0009 (4)	0.0031 (4)	−0.0041 (4)
C8	0.0170 (5)	0.0149 (5)	0.0123 (4)	−0.0019 (4)	0.0041 (4)	−0.0016 (4)
C9	0.0154 (4)	0.0109 (4)	0.0123 (4)	−0.0006 (4)	0.0031 (3)	−0.0001 (3)
C10	0.0106 (4)	0.0090 (4)	0.0107 (4)	0.0006 (3)	0.0009 (3)	−0.0001 (3)
C11	0.0112 (4)	0.0087 (4)	0.0114 (4)	0.0000 (3)	0.0004 (3)	−0.0001 (3)
C12	0.0109 (4)	0.0084 (4)	0.0097 (4)	−0.0002 (3)	0.0004 (3)	−0.0001 (3)
C13	0.0098 (4)	0.0088 (4)	0.0095 (4)	−0.0005 (3)	0.0000 (3)	−0.0009 (3)
C14	0.0118 (4)	0.0108 (4)	0.0113 (4)	0.0008 (3)	0.0020 (3)	−0.0005 (3)
C15	0.0099 (4)	0.0128 (5)	0.0146 (4)	0.0021 (4)	0.0015 (3)	0.0024 (4)
C16	0.0146 (5)	0.0194 (6)	0.0183 (5)	0.0016 (4)	0.0043 (4)	0.0062 (4)
C17	0.0147 (5)	0.0195 (6)	0.0310 (6)	−0.0005 (4)	0.0044 (4)	0.0122 (5)
C18	0.0149 (5)	0.0151 (5)	0.0362 (7)	−0.0035 (4)	−0.0012 (5)	0.0064 (5)
C19	0.0148 (5)	0.0127 (5)	0.0251 (6)	−0.0027 (4)	−0.0031 (4)	0.0012 (4)
C20	0.0116 (4)	0.0112 (5)	0.0156 (5)	−0.0006 (4)	−0.0007 (3)	0.0012 (4)
C21	0.0109 (4)	0.0083 (4)	0.0128 (4)	0.0013 (3)	−0.0014 (3)	−0.0006 (3)
C22	0.0116 (4)	0.0086 (4)	0.0108 (4)	0.0000 (3)	0.0004 (3)	−0.0005 (3)
C23	0.0116 (4)	0.0083 (4)	0.0169 (5)	0.0001 (3)	−0.0016 (3)	−0.0017 (4)
C24	0.0140 (5)	0.0142 (5)	0.0390 (7)	−0.0026 (4)	−0.0021 (5)	0.0093 (5)
C25	0.0122 (4)	0.0133 (5)	0.0219 (5)	−0.0007 (4)	−0.0038 (4)	0.0025 (4)
C26	0.0111 (4)	0.0092 (4)	0.0125 (4)	−0.0005 (3)	0.0003 (3)	0.0011 (3)
C27	0.0156 (4)	0.0132 (5)	0.0132 (4)	−0.0006 (4)	−0.0007 (3)	0.0019 (4)
C28	0.0153 (5)	0.0166 (5)	0.0188 (5)	−0.0007 (4)	−0.0029 (4)	0.0065 (4)
C29	0.0139 (5)	0.0131 (5)	0.0260 (6)	0.0023 (4)	0.0018 (4)	0.0068 (4)
C30	0.0164 (5)	0.0114 (5)	0.0215 (5)	0.0024 (4)	0.0042 (4)	0.0004 (4)
C31	0.0147 (4)	0.0105 (5)	0.0146 (4)	0.0013 (4)	0.0007 (3)	−0.0005 (4)

S1—C24	1.8058 (13)	C14—H14B	0.9900
S1—C25	1.8340 (12)	C15—C16	1.3923 (15)
O1—C1	1.2178 (12)	C15—C20	1.3961 (16)
O2—C21	1.2159 (13)	C16—C17	1.3914 (19)
N1—C25	1.4377 (14)	C16—H16A	0.9500
N1—C12	1.4589 (14)	C17—C18	1.398 (2)
N1—C23	1.4743 (14)	C17—H17A	0.9500
C1—C2	1.4724 (15)	C18—C19	1.3936 (18)
C1—C12	1.5745 (15)	C18—H18A	0.9500
C2—C3	1.3782 (15)	C19—C20	1.3939 (16)
C2—C11	1.4090 (14)	C19—H19A	0.9500
C3—C4	1.4151 (16)	C20—C21	1.4849 (15)
C3—H3A	0.9500	C22—C26	1.5152 (15)
C4—C5	1.3849 (16)	C22—C23	1.5403 (15)
C4—H4A	0.9500	C22—H22A	1.0000
C5—C6	1.4184 (16)	C23—C24	1.5502 (16)
C5—H5A	0.9500	C23—H23A	1.0000
C6—C11	1.4080 (15)	C24—H24A	0.9900
C6—C7	1.4187 (15)	C24—H24B	0.9900
C7—C8	1.3766 (17)	C25—H25A	0.9900
C7—H7A	0.9500	C25—H25B	0.9900
C8—C9	1.4227 (15)	C26—C27	1.4014 (15)
C8—H8A	0.9500	C26—C31	1.4021 (15)
C9—C10	1.3757 (14)	C27—C28	1.3898 (16)
C9—H9A	0.9500	C27—H27A	0.9500
C10—C11	1.4142 (15)	C28—C29	1.3903 (18)
C10—C12	1.5355 (14)	C28—H28A	0.9500
C12—C13	1.5842 (14)	C29—C30	1.3914 (18)
C13—C21	1.5405 (15)	C29—H29A	0.9500
C13—C22	1.5469 (15)	C30—C31	1.3938 (16)
C13—C14	1.5477 (14)	C30—H30A	0.9500
C14—C15	1.5071 (16)	C31—H31A	0.9500
C14—H14A	0.9900
C24—S1—C25	90.66 (6)	C17—C16—H16A	120.8
C25—N1—C12	118.57 (9)	C15—C16—H16A	120.8
C25—N1—C23	112.52 (9)	C16—C17—C18	121.35 (11)
C12—N1—C23	111.82 (8)	C16—C17—H17A	119.3
O1—C1—C2	127.04 (10)	C18—C17—H17A	119.3
O1—C1—C12	124.22 (10)	C19—C18—C17	120.49 (12)
C2—C1—C12	108.47 (8)	C19—C18—H18A	119.8
C3—C2—C11	120.75 (10)	C17—C18—H18A	119.8
C3—C2—C1	132.42 (10)	C18—C19—C20	117.75 (12)
C11—C2—C1	106.65 (9)	C18—C19—H19A	121.1
C2—C3—C4	117.61 (10)	C20—C19—H19A	121.1
C2—C3—H3A	121.2	C19—C20—C15	121.95 (10)
C4—C3—H3A	121.2	C19—C20—C21	129.39 (11)
C5—C4—C3	122.18 (11)	C15—C20—C21	108.61 (9)
C5—C4—H4A	118.9	O2—C21—C20	127.67 (10)
C3—C4—H4A	118.9	O2—C21—C13	125.94 (10)
C4—C5—C6	120.74 (10)	C20—C21—C13	106.38 (9)
C4—C5—H5A	119.6	C26—C22—C23	116.28 (9)
C6—C5—H5A	119.6	C26—C22—C13	115.74 (8)
C11—C6—C5	116.48 (10)	C23—C22—C13	102.74 (8)
C11—C6—C7	116.58 (10)	C26—C22—H22A	107.2
C5—C6—C7	126.94 (10)	C23—C22—H22A	107.2
C8—C7—C6	119.58 (10)	C13—C22—H22A	107.2
C8—C7—H7A	120.2	N1—C23—C22	104.53 (8)
C6—C7—H7A	120.2	N1—C23—C24	110.13 (9)
C7—C8—C9	122.68 (10)	C22—C23—C24	115.81 (10)
C7—C8—H8A	118.7	N1—C23—H23A	108.7
C9—C8—H8A	118.7	C22—C23—H23A	108.7
C10—C9—C8	119.27 (10)	C24—C23—H23A	108.7
C10—C9—H9A	120.4	C23—C24—S1	108.40 (8)
C8—C9—H9A	120.4	C23—C24—H24A	110.0
C9—C10—C11	117.72 (9)	S1—C24—H24A	110.0
C9—C10—C12	133.78 (10)	C23—C24—H24B	110.0
C11—C10—C12	108.49 (8)	S1—C24—H24B	110.0
C6—C11—C2	122.16 (10)	H24A—C24—H24B	108.4
C6—C11—C10	124.16 (9)	N1—C25—S1	107.95 (8)
C2—C11—C10	113.65 (9)	N1—C25—H25A	110.1
N1—C12—C10	119.20 (8)	S1—C25—H25A	110.1
N1—C12—C1	109.29 (8)	N1—C25—H25B	110.1
C10—C12—C1	101.25 (8)	S1—C25—H25B	110.1
N1—C12—C13	100.13 (8)	H25A—C25—H25B	108.4
C10—C12—C13	114.42 (8)	C27—C26—C31	117.89 (10)
C1—C12—C13	112.98 (8)	C27—C26—C22	119.08 (9)
C21—C13—C22	115.93 (8)	C31—C26—C22	123.02 (10)
C21—C13—C14	102.72 (8)	C28—C27—C26	121.35 (11)
C22—C13—C14	116.20 (8)	C28—C27—H27A	119.3
C21—C13—C12	111.40 (8)	C26—C27—H27A	119.3
C22—C13—C12	100.58 (8)	C27—C28—C29	120.14 (11)
C14—C13—C12	110.24 (8)	C27—C28—H28A	119.9
C15—C14—C13	102.98 (8)	C29—C28—H28A	119.9
C15—C14—H14A	111.2	C28—C29—C30	119.35 (11)
C13—C14—H14A	111.2	C28—C29—H29A	120.3
C15—C14—H14B	111.2	C30—C29—H29A	120.3
C13—C14—H14B	111.2	C29—C30—C31	120.52 (11)
H14A—C14—H14B	109.1	C29—C30—H30A	119.7
C16—C15—C20	119.94 (11)	C31—C30—H30A	119.7
C16—C15—C14	129.15 (11)	C30—C31—C26	120.73 (11)
C20—C15—C14	110.90 (9)	C30—C31—H31A	119.6
C17—C16—C15	118.45 (12)	C26—C31—H31A	119.6
O1—C1—C2—C3	11.8 (2)	C12—C13—C14—C15	−90.66 (10)
C12—C1—C2—C3	−173.99 (11)	C13—C14—C15—C16	158.41 (11)
O1—C1—C2—C11	−163.15 (11)	C13—C14—C15—C20	−22.15 (11)
C12—C1—C2—C11	11.09 (11)	C20—C15—C16—C17	−1.61 (17)
C11—C2—C3—C4	0.66 (16)	C14—C15—C16—C17	177.78 (11)
C1—C2—C3—C4	−173.68 (11)	C15—C16—C17—C18	−0.76 (18)
C2—C3—C4—C5	1.38 (17)	C16—C17—C18—C19	1.58 (19)
C3—C4—C5—C6	−1.31 (18)	C17—C18—C19—C20	0.02 (18)
C4—C5—C6—C11	−0.79 (16)	C18—C19—C20—C15	−2.44 (17)
C4—C5—C6—C7	179.17 (11)	C18—C19—C20—C21	174.76 (11)
C11—C6—C7—C8	−0.39 (16)	C16—C15—C20—C19	3.28 (17)
C5—C6—C7—C8	179.66 (12)	C14—C15—C20—C19	−176.22 (10)
C6—C7—C8—C9	−0.32 (18)	C16—C15—C20—C21	−174.43 (10)
C7—C8—C9—C10	0.68 (17)	C14—C15—C20—C21	6.07 (12)
C8—C9—C10—C11	−0.29 (16)	C19—C20—C21—O2	15.01 (19)
C8—C9—C10—C12	−179.68 (11)	C15—C20—C21—O2	−167.50 (11)
C5—C6—C11—C2	2.84 (16)	C19—C20—C21—C13	−164.61 (11)
C7—C6—C11—C2	−177.12 (10)	C15—C20—C21—C13	12.88 (12)
C5—C6—C11—C10	−179.25 (10)	C22—C13—C21—O2	26.92 (15)
C7—C6—C11—C10	0.79 (16)	C14—C13—C21—O2	154.73 (11)
C3—C2—C11—C6	−2.84 (16)	C12—C13—C21—O2	−87.27 (13)
C1—C2—C11—C6	172.80 (10)	C22—C13—C21—C20	−153.45 (9)
C3—C2—C11—C10	179.05 (10)	C14—C13—C21—C20	−25.64 (10)
C1—C2—C11—C10	−5.31 (12)	C12—C13—C21—C20	92.35 (10)
C9—C10—C11—C6	−0.45 (16)	C21—C13—C22—C26	70.82 (11)
C12—C10—C11—C6	179.09 (10)	C14—C13—C22—C26	−49.99 (12)
C9—C10—C11—C2	177.62 (10)	C12—C13—C22—C26	−168.95 (8)
C12—C10—C11—C2	−2.84 (12)	C21—C13—C22—C23	−161.38 (8)
C25—N1—C12—C10	−37.51 (14)	C14—C13—C22—C23	77.81 (10)
C23—N1—C12—C10	95.94 (11)	C12—C13—C22—C23	−41.15 (9)
C25—N1—C12—C1	78.11 (11)	C25—N1—C23—C22	140.45 (9)
C23—N1—C12—C1	−148.44 (8)	C12—N1—C23—C22	4.10 (11)
C25—N1—C12—C13	−163.03 (9)	C25—N1—C23—C24	15.42 (13)
C23—N1—C12—C13	−29.58 (10)	C12—N1—C23—C24	−120.94 (10)
C9—C10—C12—N1	−51.77 (16)	C26—C22—C23—N1	151.58 (9)
C11—C10—C12—N1	128.81 (10)	C13—C22—C23—N1	24.12 (10)
C9—C10—C12—C1	−171.57 (12)	C26—C22—C23—C24	−87.07 (12)
C11—C10—C12—C1	9.00 (10)	C13—C22—C23—C24	145.48 (9)
C9—C10—C12—C13	66.60 (15)	N1—C23—C24—S1	7.73 (12)
C11—C10—C12—C13	−112.83 (10)	C22—C23—C24—S1	−110.57 (10)
O1—C1—C12—N1	35.65 (13)	C25—S1—C24—C23	−21.26 (10)
C2—C1—C12—N1	−138.80 (9)	C12—N1—C25—S1	101.83 (9)
O1—C1—C12—C10	162.27 (10)	C23—N1—C25—S1	−31.32 (11)
C2—C1—C12—C10	−12.17 (10)	C24—S1—C25—N1	30.36 (9)
O1—C1—C12—C13	−74.89 (13)	C23—C22—C26—C27	147.99 (10)
C2—C1—C12—C13	110.66 (9)	C13—C22—C26—C27	−91.27 (12)
N1—C12—C13—C21	166.23 (8)	C23—C22—C26—C31	−32.59 (14)
C10—C12—C13—C21	37.52 (11)	C13—C22—C26—C31	88.14 (12)
C1—C12—C13—C21	−77.65 (10)	C31—C26—C27—C28	−0.97 (16)
N1—C12—C13—C22	42.79 (9)	C22—C26—C27—C28	178.47 (10)
C10—C12—C13—C22	−85.92 (10)	C26—C27—C28—C29	0.96 (17)
C1—C12—C13—C22	158.92 (8)	C27—C28—C29—C30	0.09 (17)
N1—C12—C13—C14	−80.40 (9)	C28—C29—C30—C31	−1.11 (17)
C10—C12—C13—C14	150.88 (9)	C29—C30—C31—C26	1.10 (17)
C1—C12—C13—C14	35.72 (11)	C27—C26—C31—C30	−0.06 (16)
C21—C13—C14—C15	28.15 (10)	C22—C26—C31—C30	−179.48 (10)
C22—C13—C14—C15	155.79 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O1i	0.95	2.58	3.2598 (14)	129
C23—H23A···O1ii	1.00	2.46	3.4180 (14)	160
C31—H31A···O1ii	0.95	2.56	3.4434 (14)	155
C7—H7A···O2iii	0.95	2.54	3.4111 (14)	152
C18—H18A···Cg1iv	0.95	2.91	3.5502 (14)	126
C25—H25A···Cg2v	0.99	2.68	3.5182 (13)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C6/C11 and C15–C20 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O1i	0.95	2.58	3.2598 (14)	129
C23—H23A⋯O1ii	1.00	2.46	3.4180 (14)	160
C31—H31A⋯O1ii	0.95	2.56	3.4434 (14)	155
C7—H7A⋯O2iii	0.95	2.54	3.4111 (14)	152
C18—H18A⋯Cg1iv	0.95	2.91	3.5502 (14)	126
C25—H25A⋯Cg2v	0.99	2.68	3.5182 (13)	142

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .