5-Benzyl-idene-3-phenyl-2-phenyl-imino-1,3-thia-zolidin-4-one.

The title compound, C(22)H(16)N(2)OS, is a chalcone analog with a thia-zolidinone core that was synthesized as a potential cytotoxic and anti-cancer agent. The structure is commensurately modulated by unit-cell doubling along the direction of the a axis of the cell. The two crystallographically independent mol-ecules are differerentiated by the dihedral angle between the mean planes of the benzyl-idene phenyl group against the thia-zolidin-4-one moiety, which is 5.01 (7)° in one mol-ecule, and 17.41 (6)° in the other. The two mol-ecules are otherwise close to being indistinguishable and are related by crystallographic pseudo-translation. The two mol-ecules are not planar but are slightly bent with the benzyl-idene and phenyl-imino substituents being bent upwards with respect to the center planes of the two mol-ecules. The degree of bending of the two halves of the thia-zolidin-4-one moieties (defined as the planes that inter-sect at the S atom) are 11.08 (7) and 15.88 (7)°. Packing of the mol-ecules is facilitated by C-H⋯π inter-actions and slipped π-π stacking between one of the phenyl rings and a neighboring ethylene π system [distance between the centroid of the ethylene group and the closest phenyl C atom = 3.267 (2) Å, Cg(phenyl)⋯Cg(ethylene) = 3.926 Å].

Related literature

Abdel-Aziz et al. (2010 ▶), Babu et al. (2011 ▶) and Chavda et al. (2009 ▶) describe the use of conjugated styryl ketones and related compounds as potential cytotoxic and anti­cancer agents. Satam et al. (2011 ▶) gives background to compounds with a thia­zolidinone pharmacophore and describe structures related to the title compound.

Experimental

Crystal data

C22H16N2OS

M = 356.43

Monoclinic,

a = 10.7814 (9) Å

b = 32.779 (3) Å

c = 9.8907 (8) Å

β = 98.392 (1)°

V = 3458.0 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.20 mm−1

T = 100 K

0.55 × 0.41 × 0.33 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.632, T max = 0.746

23712 measured reflections

10081 independent reflections

7732 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.125

S = 1.03

10081 reflections

469 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.23 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 and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811023658/gk2385sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023658/gk2385Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023658/gk2385Isup3.cml

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

C22H16N2OS	F(000) = 1488
Mr = 356.43	Dx = 1.369 Mg m−3
Monoclinic, P21/c	Melting point: 385 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.7814 (9) Å	Cell parameters from 6817 reflections
b = 32.779 (3) Å	θ = 2.3–30.7°
c = 9.8907 (8) Å	µ = 0.20 mm−1
β = 98.392 (1)°	T = 100 K
V = 3458.0 (5) Å3	Block, colourless
Z = 8	0.55 × 0.41 × 0.33 mm

Bruker SMART APEX CCD diffractometer	10081 independent reflections
Radiation source: fine-focus sealed tube	7732 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 31.2°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
Tmin = 0.632, Tmax = 0.746	k = −47→47
23712 measured reflections	l = −14→8

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) = 0.125	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0616P)2 + 1.0979P] where P = (Fo2 + 2Fc2)/3
10081 reflections	(Δ/σ)max < 0.001
469 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.23 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
S1A	0.37254 (3)	0.113655 (9)	0.05977 (3)	0.01578 (8)
O1A	0.20268 (10)	0.06597 (3)	0.33830 (10)	0.0250 (2)
N1A	0.45402 (11)	0.17270 (3)	0.24759 (11)	0.0165 (2)
N2A	0.34340 (10)	0.11725 (3)	0.31666 (11)	0.0153 (2)
C1A	0.39888 (12)	0.13899 (4)	0.22017 (12)	0.0146 (2)
C2A	0.26620 (13)	0.08498 (4)	0.26862 (13)	0.0172 (2)
C3A	0.27051 (12)	0.07864 (4)	0.12030 (13)	0.0162 (2)
C4A	0.19911 (13)	0.04982 (4)	0.05026 (13)	0.0185 (3)
H4A	0.1531	0.0332	0.1041	0.022*
C5A	0.18112 (12)	0.03998 (4)	−0.09501 (13)	0.0168 (2)
C6A	0.23784 (14)	0.06091 (4)	−0.19309 (14)	0.0212 (3)
H6A	0.2930	0.0829	−0.1656	0.025*
C7A	0.21457 (14)	0.04992 (5)	−0.32984 (14)	0.0236 (3)
H7A	0.2545	0.0643	−0.3949	0.028*
C8A	0.13337 (13)	0.01802 (4)	−0.37254 (14)	0.0215 (3)
H8A	0.1172	0.0108	−0.4665	0.026*
C9A	0.07626 (14)	−0.00315 (4)	−0.27756 (14)	0.0235 (3)
H9A	0.0203	−0.0249	−0.3061	0.028*
C10A	0.10086 (13)	0.00749 (4)	−0.14036 (14)	0.0211 (3)
H10A	0.0625	−0.0076	−0.0756	0.025*
C11A	0.50187 (12)	0.19422 (4)	0.14188 (12)	0.0147 (2)
C12A	0.59772 (13)	0.17841 (4)	0.07749 (14)	0.0199 (3)
H12A	0.6301	0.1520	0.1011	0.024*
C13A	0.64633 (13)	0.20112 (4)	−0.02127 (14)	0.0223 (3)
H13A	0.7124	0.1903	−0.0642	0.027*
C14A	0.59849 (14)	0.23952 (4)	−0.05721 (14)	0.0221 (3)
H14A	0.6312	0.2549	−0.1253	0.026*
C15A	0.50274 (14)	0.25535 (4)	0.00649 (15)	0.0237 (3)
H15A	0.4694	0.2815	−0.0188	0.028*
C16A	0.45523 (13)	0.23312 (4)	0.10705 (14)	0.0204 (3)
H16A	0.3911	0.2444	0.1520	0.024*
C17A	0.35528 (12)	0.13144 (4)	0.45589 (12)	0.0152 (2)
C18A	0.46121 (13)	0.12049 (4)	0.54559 (13)	0.0180 (3)
H18A	0.5230	0.1032	0.5166	0.022*
C19A	0.47534 (13)	0.13529 (4)	0.67901 (13)	0.0207 (3)
H19A	0.5470	0.1279	0.7420	0.025*
C20A	0.38492 (13)	0.16079 (4)	0.72006 (13)	0.0200 (3)
H20A	0.3958	0.1713	0.8105	0.024*
C21A	0.27842 (13)	0.17101 (4)	0.62922 (14)	0.0206 (3)
H21A	0.2161	0.1880	0.6583	0.025*
C22A	0.26323 (12)	0.15630 (4)	0.49588 (13)	0.0176 (2)
H22A	0.1909	0.1632	0.4332	0.021*
S1B	0.87010 (3)	0.114166 (10)	0.07134 (3)	0.01700 (8)
O1B	0.68006 (10)	0.07316 (3)	0.34400 (10)	0.0245 (2)
N1B	0.95837 (11)	0.17253 (3)	0.25832 (11)	0.0172 (2)
N2B	0.83667 (10)	0.11966 (3)	0.32700 (11)	0.0162 (2)
C1B	0.89758 (12)	0.13981 (4)	0.23112 (12)	0.0150 (2)
C2B	0.74959 (13)	0.09027 (4)	0.27595 (13)	0.0174 (2)
C3B	0.75375 (12)	0.08386 (4)	0.12809 (13)	0.0168 (2)
C4B	0.67166 (13)	0.05884 (4)	0.05426 (14)	0.0195 (3)
H4B	0.6119	0.0465	0.1030	0.023*
C5B	0.66074 (13)	0.04779 (4)	−0.08999 (14)	0.0195 (3)
C6B	0.75221 (14)	0.05608 (4)	−0.17333 (14)	0.0233 (3)
H6B	0.8259	0.0706	−0.1370	0.028*
C7B	0.73604 (16)	0.04329 (5)	−0.30865 (15)	0.0276 (3)
H7B	0.7981	0.0494	−0.3646	0.033*
C8B	0.62962 (16)	0.02168 (5)	−0.36239 (15)	0.0299 (3)
H8B	0.6199	0.0124	−0.4543	0.036*
C9B	0.53774 (16)	0.01368 (5)	−0.28224 (15)	0.0323 (4)
H9B	0.4645	−0.0009	−0.3193	0.039*
C10B	0.55234 (14)	0.02700 (4)	−0.14759 (15)	0.0254 (3)
H10B	0.4879	0.0219	−0.0938	0.031*
C11B	1.00800 (12)	0.19307 (4)	0.15183 (13)	0.0162 (2)
C12B	1.10058 (13)	0.17597 (4)	0.08498 (14)	0.0197 (3)
H12B	1.1308	0.1493	0.1081	0.024*
C13B	1.14876 (13)	0.19803 (4)	−0.01569 (14)	0.0225 (3)
H13B	1.2124	0.1864	−0.0606	0.027*
C14B	1.10450 (14)	0.23687 (4)	−0.05078 (14)	0.0237 (3)
H14B	1.1374	0.2518	−0.1199	0.028*
C15B	1.01203 (15)	0.25394 (4)	0.01530 (15)	0.0251 (3)
H15B	0.9811	0.2805	−0.0092	0.030*
C16B	0.96464 (14)	0.23236 (4)	0.11700 (14)	0.0214 (3)
H16B	0.9024	0.2444	0.1632	0.026*
C17B	0.84998 (12)	0.13379 (4)	0.46609 (13)	0.0164 (2)
C18B	0.95529 (13)	0.12222 (4)	0.55533 (14)	0.0203 (3)
H18B	1.0158	0.1045	0.5260	0.024*
C19B	0.97085 (13)	0.13698 (4)	0.68874 (14)	0.0229 (3)
H19B	1.0423	0.1293	0.7514	0.027*
C20B	0.88194 (13)	0.16298 (4)	0.73020 (14)	0.0216 (3)
H20B	0.8935	0.1733	0.8209	0.026*
C21B	0.77625 (13)	0.17394 (4)	0.63987 (14)	0.0215 (3)
H21B	0.7153	0.1915	0.6691	0.026*
C22B	0.75968 (13)	0.15919 (4)	0.50639 (14)	0.0192 (3)
H22B	0.6875	0.1664	0.4440	0.023*

	U11	U22	U33	U12	U13	U23
S1A	0.01872 (16)	0.01662 (15)	0.01241 (15)	−0.00329 (11)	0.00371 (11)	−0.00114 (10)
O1A	0.0353 (6)	0.0255 (5)	0.0152 (5)	−0.0138 (4)	0.0071 (4)	−0.0009 (4)
N1A	0.0200 (6)	0.0162 (5)	0.0136 (5)	−0.0024 (4)	0.0030 (4)	0.0006 (4)
N2A	0.0190 (5)	0.0150 (5)	0.0122 (5)	−0.0037 (4)	0.0030 (4)	0.0003 (4)
C1A	0.0159 (6)	0.0158 (5)	0.0121 (6)	0.0010 (4)	0.0019 (4)	0.0009 (4)
C2A	0.0212 (6)	0.0158 (5)	0.0145 (6)	−0.0023 (5)	0.0023 (5)	0.0004 (4)
C3A	0.0194 (6)	0.0152 (5)	0.0142 (6)	−0.0018 (5)	0.0032 (5)	0.0009 (4)
C4A	0.0229 (7)	0.0184 (6)	0.0146 (6)	−0.0044 (5)	0.0034 (5)	0.0004 (5)
C5A	0.0182 (6)	0.0174 (6)	0.0146 (6)	−0.0008 (5)	0.0016 (5)	−0.0010 (4)
C6A	0.0262 (7)	0.0214 (6)	0.0159 (6)	−0.0055 (5)	0.0025 (5)	−0.0007 (5)
C7A	0.0270 (7)	0.0292 (7)	0.0149 (6)	−0.0051 (6)	0.0038 (5)	0.0006 (5)
C8A	0.0227 (7)	0.0274 (7)	0.0134 (6)	0.0015 (5)	−0.0010 (5)	−0.0030 (5)
C9A	0.0247 (7)	0.0238 (7)	0.0211 (7)	−0.0040 (5)	0.0003 (5)	−0.0054 (5)
C10A	0.0233 (7)	0.0214 (6)	0.0187 (7)	−0.0043 (5)	0.0038 (5)	−0.0023 (5)
C11A	0.0164 (6)	0.0150 (5)	0.0123 (6)	−0.0035 (4)	0.0009 (4)	−0.0006 (4)
C12A	0.0196 (6)	0.0200 (6)	0.0203 (7)	0.0013 (5)	0.0036 (5)	0.0028 (5)
C13A	0.0201 (7)	0.0265 (7)	0.0212 (7)	−0.0006 (5)	0.0058 (5)	0.0010 (5)
C14A	0.0246 (7)	0.0244 (7)	0.0171 (7)	−0.0063 (5)	0.0025 (5)	0.0045 (5)
C15A	0.0279 (7)	0.0180 (6)	0.0251 (7)	−0.0002 (5)	0.0034 (6)	0.0055 (5)
C16A	0.0229 (7)	0.0178 (6)	0.0211 (7)	0.0001 (5)	0.0057 (5)	0.0004 (5)
C17A	0.0194 (6)	0.0155 (5)	0.0107 (6)	−0.0041 (5)	0.0023 (4)	−0.0002 (4)
C18A	0.0179 (6)	0.0192 (6)	0.0168 (6)	−0.0003 (5)	0.0024 (5)	0.0019 (5)
C19A	0.0199 (7)	0.0267 (7)	0.0146 (6)	−0.0033 (5)	−0.0007 (5)	0.0019 (5)
C20A	0.0253 (7)	0.0227 (6)	0.0123 (6)	−0.0071 (5)	0.0034 (5)	−0.0006 (5)
C21A	0.0220 (7)	0.0229 (6)	0.0180 (7)	−0.0021 (5)	0.0070 (5)	−0.0024 (5)
C22A	0.0173 (6)	0.0192 (6)	0.0162 (6)	−0.0015 (5)	0.0018 (5)	0.0007 (5)
S1B	0.01907 (17)	0.01822 (15)	0.01406 (16)	−0.00326 (11)	0.00352 (12)	−0.00196 (11)
O1B	0.0306 (6)	0.0250 (5)	0.0192 (5)	−0.0105 (4)	0.0082 (4)	−0.0019 (4)
N1B	0.0190 (5)	0.0175 (5)	0.0152 (5)	−0.0015 (4)	0.0025 (4)	0.0002 (4)
N2B	0.0185 (5)	0.0175 (5)	0.0130 (5)	−0.0028 (4)	0.0031 (4)	−0.0006 (4)
C1B	0.0151 (6)	0.0171 (5)	0.0126 (6)	0.0011 (4)	0.0016 (4)	0.0000 (4)
C2B	0.0198 (6)	0.0153 (5)	0.0169 (6)	−0.0017 (5)	0.0027 (5)	−0.0011 (4)
C3B	0.0191 (6)	0.0161 (5)	0.0156 (6)	−0.0014 (5)	0.0039 (5)	−0.0009 (4)
C4B	0.0214 (7)	0.0178 (6)	0.0193 (7)	−0.0028 (5)	0.0035 (5)	−0.0006 (5)
C5B	0.0236 (7)	0.0170 (6)	0.0172 (6)	−0.0012 (5)	0.0003 (5)	−0.0004 (5)
C6B	0.0258 (7)	0.0234 (6)	0.0208 (7)	−0.0048 (5)	0.0035 (5)	−0.0043 (5)
C7B	0.0349 (9)	0.0298 (7)	0.0188 (7)	−0.0031 (6)	0.0065 (6)	−0.0029 (6)
C8B	0.0370 (9)	0.0350 (8)	0.0156 (7)	−0.0032 (7)	−0.0028 (6)	−0.0031 (6)
C9B	0.0336 (9)	0.0403 (9)	0.0202 (7)	−0.0108 (7)	−0.0054 (6)	−0.0034 (6)
C10B	0.0266 (8)	0.0277 (7)	0.0207 (7)	−0.0041 (6)	−0.0009 (6)	0.0011 (5)
C11B	0.0169 (6)	0.0171 (5)	0.0139 (6)	−0.0042 (5)	0.0004 (5)	−0.0004 (4)
C12B	0.0181 (6)	0.0201 (6)	0.0208 (7)	0.0008 (5)	0.0021 (5)	0.0028 (5)
C13B	0.0184 (7)	0.0284 (7)	0.0209 (7)	−0.0006 (5)	0.0040 (5)	0.0012 (5)
C14B	0.0243 (7)	0.0271 (7)	0.0190 (7)	−0.0066 (6)	0.0012 (5)	0.0054 (5)
C15B	0.0302 (8)	0.0189 (6)	0.0257 (7)	−0.0014 (5)	0.0020 (6)	0.0046 (5)
C16B	0.0233 (7)	0.0189 (6)	0.0222 (7)	0.0002 (5)	0.0043 (5)	0.0001 (5)
C17B	0.0196 (6)	0.0171 (6)	0.0126 (6)	−0.0041 (5)	0.0027 (5)	−0.0001 (4)
C18B	0.0198 (7)	0.0226 (6)	0.0182 (7)	0.0003 (5)	0.0019 (5)	0.0000 (5)
C19B	0.0213 (7)	0.0291 (7)	0.0171 (7)	−0.0021 (5)	−0.0012 (5)	0.0021 (5)
C20B	0.0235 (7)	0.0270 (7)	0.0142 (6)	−0.0068 (5)	0.0028 (5)	−0.0019 (5)
C21B	0.0212 (7)	0.0260 (7)	0.0180 (7)	−0.0008 (5)	0.0056 (5)	−0.0022 (5)
C22B	0.0181 (6)	0.0221 (6)	0.0171 (6)	−0.0008 (5)	0.0023 (5)	−0.0001 (5)

S1A—C3A	1.7544 (13)	S1B—C3B	1.7553 (13)
S1A—C1A	1.7764 (13)	S1B—C1B	1.7762 (13)
O1A—C2A	1.2124 (15)	O1B—C2B	1.2151 (16)
N1A—C1A	1.2653 (16)	N1B—C1B	1.2654 (16)
N1A—C11A	1.4192 (16)	N1B—C11B	1.4189 (16)
N2A—C2A	1.3863 (16)	N2B—C2B	1.3879 (16)
N2A—C1A	1.3940 (16)	N2B—C1B	1.3960 (16)
N2A—C17A	1.4414 (15)	N2B—C17B	1.4387 (16)
C2A—C3A	1.4891 (17)	C2B—C3B	1.4846 (18)
C3A—C4A	1.3452 (17)	C3B—C4B	1.3418 (18)
C4A—C5A	1.4577 (18)	C4B—C5B	1.4600 (18)
C4A—H4A	0.9500	C4B—H4B	0.9500
C5A—C6A	1.3997 (18)	C5B—C10B	1.4003 (19)
C5A—C10A	1.4039 (18)	C5B—C6B	1.401 (2)
C6A—C7A	1.3867 (19)	C6B—C7B	1.389 (2)
C6A—H6A	0.9500	C6B—H6B	0.9500
C7A—C8A	1.3893 (19)	C7B—C8B	1.387 (2)
C7A—H7A	0.9500	C7B—H7B	0.9500
C8A—C9A	1.383 (2)	C8B—C9B	1.381 (2)
C8A—H8A	0.9500	C8B—H8B	0.9500
C9A—C10A	1.3887 (19)	C9B—C10B	1.388 (2)
C9A—H9A	0.9500	C9B—H9B	0.9500
C10A—H10A	0.9500	C10B—H10B	0.9500
C11A—C12A	1.3909 (18)	C11B—C12B	1.3930 (19)
C11A—C16A	1.3952 (18)	C11B—C16B	1.3960 (18)
C12A—C13A	1.3902 (19)	C12B—C13B	1.3912 (19)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—C14A	1.387 (2)	C13B—C14B	1.386 (2)
C13A—H13A	0.9500	C13B—H13B	0.9500
C14A—C15A	1.386 (2)	C14B—C15B	1.387 (2)
C14A—H14A	0.9500	C14B—H14B	0.9500
C15A—C16A	1.3898 (19)	C15B—C16B	1.3868 (19)
C15A—H15A	0.9500	C15B—H15B	0.9500
C16A—H16A	0.9500	C16B—H16B	0.9500
C17A—C22A	1.3855 (18)	C17B—C22B	1.3831 (19)
C17A—C18A	1.3873 (18)	C17B—C18B	1.3854 (18)
C18A—C19A	1.3933 (18)	C18B—C19B	1.3925 (19)
C18A—H18A	0.9500	C18B—H18B	0.9500
C19A—C20A	1.389 (2)	C19B—C20B	1.389 (2)
C19A—H19A	0.9500	C19B—H19B	0.9500
C20A—C21A	1.3917 (19)	C20B—C21B	1.389 (2)
C20A—H20A	0.9500	C20B—H20B	0.9500
C21A—C22A	1.3914 (18)	C21B—C22B	1.3928 (18)
C21A—H21A	0.9500	C21B—H21B	0.9500
C22A—H22A	0.9500	C22B—H22B	0.9500
C3A—S1A—C1A	91.58 (6)	C3B—S1B—C1B	91.01 (6)
C1A—N1A—C11A	119.08 (11)	C1B—N1B—C11B	118.95 (11)
C2A—N2A—C1A	116.85 (10)	C2B—N2B—C1B	116.21 (10)
C2A—N2A—C17A	122.60 (10)	C2B—N2B—C17B	122.62 (11)
C1A—N2A—C17A	120.13 (10)	C1B—N2B—C17B	120.41 (10)
N1A—C1A—N2A	122.34 (11)	N1B—C1B—N2B	122.48 (11)
N1A—C1A—S1A	127.49 (10)	N1B—C1B—S1B	127.18 (10)
N2A—C1A—S1A	110.10 (9)	N2B—C1B—S1B	110.28 (9)
O1A—C2A—N2A	123.92 (12)	O1B—C2B—N2B	123.92 (12)
O1A—C2A—C3A	126.13 (12)	O1B—C2B—C3B	126.16 (12)
N2A—C2A—C3A	109.91 (11)	N2B—C2B—C3B	109.91 (11)
C4A—C3A—C2A	120.50 (12)	C4B—C3B—C2B	120.68 (12)
C4A—C3A—S1A	128.61 (10)	C4B—C3B—S1B	128.12 (10)
C2A—C3A—S1A	110.86 (9)	C2B—C3B—S1B	111.14 (9)
C3A—C4A—C5A	130.30 (12)	C3B—C4B—C5B	129.51 (13)
C3A—C4A—H4A	114.8	C3B—C4B—H4B	115.2
C5A—C4A—H4A	114.8	C5B—C4B—H4B	115.2
C6A—C5A—C10A	117.50 (12)	C10B—C5B—C6B	118.19 (13)
C6A—C5A—C4A	124.47 (12)	C10B—C5B—C4B	117.50 (13)
C10A—C5A—C4A	118.03 (12)	C6B—C5B—C4B	124.30 (13)
C7A—C6A—C5A	120.90 (13)	C7B—C6B—C5B	120.54 (14)
C7A—C6A—H6A	119.6	C7B—C6B—H6B	119.7
C5A—C6A—H6A	119.6	C5B—C6B—H6B	119.7
C6A—C7A—C8A	120.55 (13)	C8B—C7B—C6B	120.27 (14)
C6A—C7A—H7A	119.7	C8B—C7B—H7B	119.9
C8A—C7A—H7A	119.7	C6B—C7B—H7B	119.9
C9A—C8A—C7A	119.64 (12)	C9B—C8B—C7B	119.97 (14)
C9A—C8A—H8A	120.2	C9B—C8B—H8B	120.0
C7A—C8A—H8A	120.2	C7B—C8B—H8B	120.0
C8A—C9A—C10A	119.83 (13)	C8B—C9B—C10B	120.04 (14)
C8A—C9A—H9A	120.1	C8B—C9B—H9B	120.0
C10A—C9A—H9A	120.1	C10B—C9B—H9B	120.0
C9A—C10A—C5A	121.57 (13)	C9B—C10B—C5B	120.95 (14)
C9A—C10A—H10A	119.2	C9B—C10B—H10B	119.5
C5A—C10A—H10A	119.2	C5B—C10B—H10B	119.5
C12A—C11A—C16A	119.51 (12)	C12B—C11B—C16B	119.44 (12)
C12A—C11A—N1A	121.76 (11)	C12B—C11B—N1B	122.37 (12)
C16A—C11A—N1A	118.65 (11)	C16B—C11B—N1B	118.16 (12)
C13A—C12A—C11A	120.24 (12)	C13B—C12B—C11B	119.92 (13)
C13A—C12A—H12A	119.9	C13B—C12B—H12B	120.0
C11A—C12A—H12A	119.9	C11B—C12B—H12B	120.0
C14A—C13A—C12A	120.13 (13)	C14B—C13B—C12B	120.39 (13)
C14A—C13A—H13A	119.9	C14B—C13B—H13B	119.8
C12A—C13A—H13A	119.9	C12B—C13B—H13B	119.8
C15A—C14A—C13A	119.81 (13)	C13B—C14B—C15B	119.84 (13)
C15A—C14A—H14A	120.1	C13B—C14B—H14B	120.1
C13A—C14A—H14A	120.1	C15B—C14B—H14B	120.1
C14A—C15A—C16A	120.37 (13)	C16B—C15B—C14B	120.13 (13)
C14A—C15A—H15A	119.8	C16B—C15B—H15B	119.9
C16A—C15A—H15A	119.8	C14B—C15B—H15B	119.9
C15A—C16A—C11A	119.92 (13)	C15B—C16B—C11B	120.27 (13)
C15A—C16A—H16A	120.0	C15B—C16B—H16B	119.9
C11A—C16A—H16A	120.0	C11B—C16B—H16B	119.9
C22A—C17A—C18A	121.78 (12)	C22B—C17B—C18B	121.81 (12)
C22A—C17A—N2A	119.68 (11)	C22B—C17B—N2B	119.55 (12)
C18A—C17A—N2A	118.52 (11)	C18B—C17B—N2B	118.63 (12)
C17A—C18A—C19A	118.80 (12)	C17B—C18B—C19B	118.86 (13)
C17A—C18A—H18A	120.6	C17B—C18B—H18B	120.6
C19A—C18A—H18A	120.6	C19B—C18B—H18B	120.6
C20A—C19A—C18A	120.13 (13)	C20B—C19B—C18B	120.02 (13)
C20A—C19A—H19A	119.9	C20B—C19B—H19B	120.0
C18A—C19A—H19A	119.9	C18B—C19B—H19B	120.0
C19A—C20A—C21A	120.29 (12)	C19B—C20B—C21B	120.38 (13)
C19A—C20A—H20A	119.9	C19B—C20B—H20B	119.8
C21A—C20A—H20A	119.9	C21B—C20B—H20B	119.8
C22A—C21A—C20A	120.02 (13)	C20B—C21B—C22B	119.97 (13)
C22A—C21A—H21A	120.0	C20B—C21B—H21B	120.0
C20A—C21A—H21A	120.0	C22B—C21B—H21B	120.0
C17A—C22A—C21A	118.97 (12)	C17B—C22B—C21B	118.94 (13)
C17A—C22A—H22A	120.5	C17B—C22B—H22B	120.5
C21A—C22A—H22A	120.5	C21B—C22B—H22B	120.5
C11A—N1A—C1A—N2A	−176.35 (11)	C11B—N1B—C1B—N2B	−174.35 (11)
C11A—N1A—C1A—S1A	0.28 (18)	C11B—N1B—C1B—S1B	2.64 (18)
C2A—N2A—C1A—N1A	168.24 (12)	C2B—N2B—C1B—N1B	164.86 (12)
C17A—N2A—C1A—N1A	−4.49 (19)	C17B—N2B—C1B—N1B	−5.38 (19)
C2A—N2A—C1A—S1A	−8.91 (14)	C2B—N2B—C1B—S1B	−12.58 (14)
C17A—N2A—C1A—S1A	178.36 (9)	C17B—N2B—C1B—S1B	177.18 (9)
C3A—S1A—C1A—N1A	−169.45 (13)	C3B—S1B—C1B—N1B	−166.12 (13)
C3A—S1A—C1A—N2A	7.52 (10)	C3B—S1B—C1B—N2B	11.17 (10)
C1A—N2A—C2A—O1A	−172.66 (13)	C1B—N2B—C2B—O1B	−172.17 (13)
C17A—N2A—C2A—O1A	−0.1 (2)	C17B—N2B—C2B—O1B	−2.2 (2)
C1A—N2A—C2A—C3A	5.38 (16)	C1B—N2B—C2B—C3B	6.89 (16)
C17A—N2A—C2A—C3A	177.92 (11)	C17B—N2B—C2B—C3B	176.89 (11)
O1A—C2A—C3A—C4A	0.5 (2)	O1B—C2B—C3B—C4B	3.7 (2)
N2A—C2A—C3A—C4A	−177.54 (12)	N2B—C2B—C3B—C4B	−175.32 (12)
O1A—C2A—C3A—S1A	178.68 (12)	O1B—C2B—C3B—S1B	−178.94 (12)
N2A—C2A—C3A—S1A	0.69 (14)	N2B—C2B—C3B—S1B	2.02 (14)
C1A—S1A—C3A—C4A	173.38 (13)	C1B—S1B—C3B—C4B	169.61 (13)
C1A—S1A—C3A—C2A	−4.67 (10)	C1B—S1B—C3B—C2B	−7.49 (10)
C2A—C3A—C4A—C5A	175.30 (13)	C2B—C3B—C4B—C5B	−178.83 (13)
S1A—C3A—C4A—C5A	−2.6 (2)	S1B—C3B—C4B—C5B	4.3 (2)
C3A—C4A—C5A—C6A	−1.2 (2)	C3B—C4B—C5B—C10B	−168.33 (14)
C3A—C4A—C5A—C10A	179.25 (14)	C3B—C4B—C5B—C6B	12.7 (2)
C10A—C5A—C6A—C7A	0.4 (2)	C10B—C5B—C6B—C7B	−1.1 (2)
C4A—C5A—C6A—C7A	−179.19 (13)	C4B—C5B—C6B—C7B	177.88 (13)
C5A—C6A—C7A—C8A	0.6 (2)	C5B—C6B—C7B—C8B	−0.8 (2)
C6A—C7A—C8A—C9A	−0.6 (2)	C6B—C7B—C8B—C9B	1.6 (2)
C7A—C8A—C9A—C10A	−0.3 (2)	C7B—C8B—C9B—C10B	−0.5 (3)
C8A—C9A—C10A—C5A	1.2 (2)	C8B—C9B—C10B—C5B	−1.5 (2)
C6A—C5A—C10A—C9A	−1.3 (2)	C6B—C5B—C10B—C9B	2.2 (2)
C4A—C5A—C10A—C9A	178.32 (13)	C4B—C5B—C10B—C9B	−176.82 (14)
C1A—N1A—C11A—C12A	−64.30 (17)	C1B—N1B—C11B—C12B	−64.65 (17)
C1A—N1A—C11A—C16A	118.93 (14)	C1B—N1B—C11B—C16B	117.54 (14)
C16A—C11A—C12A—C13A	−0.3 (2)	C16B—C11B—C12B—C13B	−0.1 (2)
N1A—C11A—C12A—C13A	−177.02 (12)	N1B—C11B—C12B—C13B	−177.89 (12)
C11A—C12A—C13A—C14A	−0.7 (2)	C11B—C12B—C13B—C14B	−0.5 (2)
C12A—C13A—C14A—C15A	0.6 (2)	C12B—C13B—C14B—C15B	0.3 (2)
C13A—C14A—C15A—C16A	0.6 (2)	C13B—C14B—C15B—C16B	0.5 (2)
C14A—C15A—C16A—C11A	−1.6 (2)	C14B—C15B—C16B—C11B	−1.1 (2)
C12A—C11A—C16A—C15A	1.4 (2)	C12B—C11B—C16B—C15B	0.9 (2)
N1A—C11A—C16A—C15A	178.27 (12)	N1B—C11B—C16B—C15B	178.82 (12)
C2A—N2A—C17A—C22A	−79.01 (16)	C2B—N2B—C17B—C22B	−73.31 (16)
C1A—N2A—C17A—C22A	93.29 (15)	C1B—N2B—C17B—C22B	96.28 (15)
C2A—N2A—C17A—C18A	102.61 (15)	C2B—N2B—C17B—C18B	108.23 (15)
C1A—N2A—C17A—C18A	−85.09 (15)	C1B—N2B—C17B—C18B	−82.17 (16)
C22A—C17A—C18A—C19A	−0.57 (19)	C22B—C17B—C18B—C19B	−0.7 (2)
N2A—C17A—C18A—C19A	177.78 (11)	N2B—C17B—C18B—C19B	177.73 (12)
C17A—C18A—C19A—C20A	−0.5 (2)	C17B—C18B—C19B—C20B	−0.3 (2)
C18A—C19A—C20A—C21A	1.4 (2)	C18B—C19B—C20B—C21B	1.0 (2)
C19A—C20A—C21A—C22A	−1.2 (2)	C19B—C20B—C21B—C22B	−0.7 (2)
C18A—C17A—C22A—C21A	0.78 (19)	C18B—C17B—C22B—C21B	0.9 (2)
N2A—C17A—C22A—C21A	−177.56 (11)	N2B—C17B—C22B—C21B	−177.47 (12)
C20A—C21A—C22A—C17A	0.1 (2)	C20B—C21B—C22B—C17B	−0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C12A—H12A···S1B	0.95	2.92	3.6214 (15)	131
C12A—H12A···C2B	0.95	2.85	3.7340 (19)	156
C12A—H12A···C3B	0.95	2.59	3.5270 (19)	167
C12B—H12B···S1Ai	0.95	2.96	3.6118 (15)	127
C12B—H12B···C3Ai	0.95	2.76	3.6700 (19)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12A—H12A⋯S1B	0.95	2.92	3.6214 (15)	131
C12A—H12A⋯C2B	0.95	2.85	3.7340 (19)	156
C12A—H12A⋯C3B	0.95	2.59	3.5270 (19)	167
C12B—H12B⋯S1Ai	0.95	2.96	3.6118 (15)	127
C12B—H12B⋯C3Ai	0.95	2.76	3.6700 (19)	162

Symmetry code: (i) .