Methyl (2Z)-((2Z)-2-{(2E)-[1-(4-methyl-phen-yl)ethyl-idene]hydrazinyl-idene}-4-oxo-3-phenyl-1,3-thia-zolidin-5-yl-idene)ethano-ate.

The asymmetric unit of the title compound, C21H19N3O3S, contains two independent mol-ecules. In one mol-ecule, the 1,3-thia-zolidine ring forms dihedral angles of 86.19 (8) and 8.37 (8)° with the phenyl and benzene rings, respectively. The corresponding dihedral angles in the other mol-ecule are 69.60 (7) and 14.08 (7)°. The dihedral angle between the phenyl and benzene rings is 84.70 (8)° in one mol-ecule and 69.62 (8)° in the other. In the crystal, mol-ecules pack in layers approximately parallel to (10-2). There are weak C-H⋯O hydrogen bonds within these layers. Further weak C-H⋯O hydrogen bonding occurs between the layers to form a three-dimensional network. A weak C-H⋯π inter-action is also observed.

Related literature

For the synthesis and general applications of thia­zolidines, see: Pandey et al. (2011 ▶); Barreca et al. (2002 ▶); Botti et al. (1996 ▶); Pfahl et al. (2003 ▶); Sayyed et al. (2006 ▶); Sharma et al. (2006 ▶); Babaoğlu et al. (2003 ▶); Çapan et al. (1999 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C21H19N3O3S

M = 393.46

Monoclinic,

a = 8.3713 (12) Å

b = 21.568 (3) Å

c = 21.591 (3) Å

β = 96.411 (2)°

V = 3873.9 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.19 mm−1

T = 150 K

0.19 × 0.19 × 0.11 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.81, T max = 0.98

69242 measured reflections

9850 independent reflections

7890 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.112

S = 1.05

9850 reflections

511 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Putz, 2012 ▶).; software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813021533/lh5636sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813021533/lh5636Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813021533/lh5636Isup3.cml

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

C21H19N3O3S	F(000) = 1648
Mr = 393.46	Dx = 1.349 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9179 reflections
a = 8.3713 (12) Å	θ = 2.5–28.6°
b = 21.568 (3) Å	µ = 0.19 mm−1
c = 21.591 (3) Å	T = 150 K
β = 96.411 (2)°	Block, clear yellow
V = 3873.9 (9) Å3	0.19 × 0.19 × 0.11 mm
Z = 8

Bruker SMART APEX CCD diffractometer	9850 independent reflections
Radiation source: fine-focus sealed tube	7890 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
Detector resolution: 8.3660 pixels mm-1	θmax = 28.6°, θmin = 1.9°
φ and ω scans	h = −10→11
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −28→28
Tmin = 0.81, Tmax = 0.98	l = −28→28
69242 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.112	W = 1/[Σ2(FO2) + (0.0511P)2 + 1.054P] WHERE P = (FO2 + 2FC2)/3
S = 1.05	(Δ/σ)max = 0.001
9850 reflections	Δρmax = 0.34 e Å−3
511 parameters	Δρmin = −0.34 e Å−3

Experimental. 1H-NMR [δ, p.p.m., CDCl3]: 2.27 (S, 3H, CH3), 2.39 (S, 3H, CH3), 3.88 (S, 3H, OCH3), 6.97 (S, 1H, vinyl - CH), 7.19–7.26 (m, 2H, Ar- H), 7.44–7.47 (m, 3H, Ar - H), 7.51–7.55 (m, 2H, Ar - H), 7.78–7.83 (m, 2H, Ar - H). 13C-NMR [δ, p.p.m., CDCl3]: 15.03 (CH3), 21.42 (CH3), 52.49 (OCH3), 115.98 (vinyl-CH), 126.92, 127.46, 128.90, 129.09, 129.30 (Ar - CH), 132.21, 133.76 (Ar - C), 140.75 (Ar – C– N), 142.05 (CH3 – C=N), 158.15 (thiazole – C.2), 164.9 (cyclic – C=O), 166.59 (ester - CO).

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.59531 (4)	0.00119 (2)	0.42718 (2)	0.0226 (1)
O1	0.79183 (14)	0.14802 (5)	0.50471 (5)	0.0337 (3)
O2	0.74230 (14)	−0.08842 (5)	0.50854 (5)	0.0302 (3)
O3	0.93261 (13)	−0.06779 (5)	0.58848 (5)	0.0285 (3)
N1	0.60347 (15)	0.12318 (6)	0.42279 (6)	0.0241 (3)
N2	0.42172 (15)	0.07810 (6)	0.34568 (6)	0.0263 (4)
N3	0.36391 (15)	0.01878 (6)	0.32675 (6)	0.0260 (4)
C1	0.52809 (17)	0.07228 (7)	0.39283 (7)	0.0228 (4)
C2	0.71496 (18)	0.10956 (7)	0.47312 (7)	0.0250 (4)
C3	0.72573 (17)	0.04065 (6)	0.48243 (7)	0.0227 (4)
C4	0.82274 (18)	0.01562 (7)	0.52956 (7)	0.0247 (4)
C5	0.82622 (18)	−0.05181 (7)	0.53990 (7)	0.0244 (4)
C6	0.9370 (2)	−0.13330 (7)	0.60373 (8)	0.0319 (5)
C7	0.55457 (18)	0.18631 (6)	0.40694 (7)	0.0244 (4)
C8	0.4378 (2)	0.21376 (7)	0.43831 (8)	0.0306 (5)
C9	0.3904 (2)	0.27400 (8)	0.42290 (9)	0.0368 (5)
C10	0.4589 (2)	0.30597 (7)	0.37721 (8)	0.0367 (5)
C11	0.5760 (2)	0.27798 (8)	0.34637 (8)	0.0389 (6)
C12	0.6251 (2)	0.21778 (8)	0.36116 (8)	0.0334 (5)
C13	0.25712 (18)	0.01879 (7)	0.27854 (7)	0.0260 (4)
C14	0.1978 (2)	0.07602 (8)	0.24368 (8)	0.0346 (5)
C15	0.19100 (18)	−0.04256 (8)	0.25778 (7)	0.0279 (4)
C16	0.2319 (2)	−0.09620 (8)	0.29201 (8)	0.0367 (5)
C17	0.1656 (2)	−0.15299 (8)	0.27352 (9)	0.0408 (6)
C18	0.0564 (2)	−0.15848 (9)	0.22020 (9)	0.0390 (6)
C19	0.0179 (2)	−0.10561 (9)	0.18561 (9)	0.0436 (6)
C20	0.0840 (2)	−0.04854 (9)	0.20358 (8)	0.0373 (5)
C21	−0.0198 (3)	−0.22033 (10)	0.20217 (11)	0.0575 (8)
S2	0.57525 (4)	−0.01716 (2)	0.19020 (2)	0.0234 (1)
O4	0.79280 (13)	0.12820 (5)	0.26255 (5)	0.0291 (3)
O5	0.70484 (14)	−0.10494 (5)	0.27998 (5)	0.0326 (3)
O6	0.89186 (13)	−0.08142 (5)	0.36026 (5)	0.0286 (3)
N4	0.60388 (15)	0.10390 (5)	0.18031 (6)	0.0229 (3)
N5	0.42977 (16)	0.06042 (6)	0.10082 (6)	0.0266 (4)
N6	0.35687 (16)	0.00405 (6)	0.08093 (6)	0.0266 (4)
C22	0.52529 (17)	0.05328 (6)	0.15065 (7)	0.0230 (4)
C23	0.70949 (17)	0.09035 (6)	0.23226 (7)	0.0222 (4)
C24	0.70620 (17)	0.02231 (6)	0.24547 (7)	0.0221 (4)
C25	0.79655 (17)	−0.00146 (6)	0.29468 (7)	0.0230 (4)
C26	0.79111 (18)	−0.06797 (7)	0.30954 (7)	0.0239 (4)
C27	0.8927 (2)	−0.14517 (7)	0.38080 (8)	0.0350 (5)
C28	0.57567 (17)	0.16650 (6)	0.15832 (7)	0.0244 (4)
C29	0.49625 (19)	0.20722 (7)	0.19350 (8)	0.0313 (5)
C30	0.4714 (2)	0.26784 (8)	0.17250 (9)	0.0401 (6)
C31	0.5262 (2)	0.28624 (8)	0.11736 (9)	0.0429 (6)
C32	0.6065 (2)	0.24503 (8)	0.08284 (9)	0.0415 (6)
C33	0.6307 (2)	0.18437 (7)	0.10301 (8)	0.0329 (5)
C34	0.28762 (18)	0.00516 (7)	0.02447 (7)	0.0246 (4)
C35	0.2913 (2)	0.05937 (7)	−0.01919 (7)	0.0321 (5)
C36	0.19741 (18)	−0.05168 (7)	0.00294 (7)	0.0257 (4)
C37	0.2025 (2)	−0.10475 (7)	0.03991 (8)	0.0310 (5)
C38	0.1130 (2)	−0.15691 (8)	0.02074 (8)	0.0358 (5)
C39	0.0141 (2)	−0.15761 (8)	−0.03558 (8)	0.0360 (5)
C40	0.0101 (2)	−0.10492 (8)	−0.07239 (9)	0.0404 (5)
C41	0.1002 (2)	−0.05263 (8)	−0.05402 (8)	0.0343 (5)
C42	−0.0846 (3)	−0.21374 (10)	−0.05661 (11)	0.0567 (8)
H4	0.89000	0.04180	0.55660	0.0300*
H6A	0.83230	−0.14610	0.61550	0.0480*
H6B	1.02020	−0.14080	0.63860	0.0480*
H6C	0.96160	−0.15720	0.56740	0.0480*
H8	0.39080	0.19180	0.46980	0.0370*
H9	0.31010	0.29340	0.44400	0.0440*
H10	0.42570	0.34720	0.36690	0.0440*
H11	0.62300	0.30010	0.31490	0.0470*
H12	0.70590	0.19850	0.34020	0.0400*
H14A	0.24530	0.11280	0.26520	0.0520*
H14B	0.08040	0.07820	0.24180	0.0520*
H14C	0.22890	0.07450	0.20130	0.0520*
H16	0.30630	−0.09370	0.32850	0.0440*
H17	0.19520	−0.18890	0.29760	0.0490*
H19	−0.05520	−0.10840	0.14880	0.0520*
H20	0.05610	−0.01300	0.17870	0.0450*
H21A	−0.12960	−0.22130	0.21390	0.0860*
H21B	0.04350	−0.25360	0.22390	0.0860*
H21C	−0.02270	−0.22620	0.15700	0.0860*
H25	0.86560	0.02510	0.32060	0.0280*
H27A	0.79620	−0.15330	0.40140	0.0530*
H27B	0.98860	−0.15280	0.41020	0.0530*
H27C	0.89380	−0.17270	0.34480	0.0530*
H29	0.45920	0.19410	0.23140	0.0380*
H30	0.41680	0.29650	0.19610	0.0480*
H31	0.50860	0.32760	0.10310	0.0510*
H32	0.64510	0.25830	0.04530	0.0500*
H33	0.68420	0.15560	0.07920	0.0400*
H35A	0.35810	0.09240	0.00130	0.0480*
H35B	0.18180	0.07490	−0.03020	0.0480*
H35C	0.33650	0.04620	−0.05700	0.0480*
H37	0.26800	−0.10530	0.07880	0.0370*
H38	0.11930	−0.19270	0.04650	0.0430*
H40	−0.05590	−0.10450	−0.11120	0.0480*
H41	0.09570	−0.01730	−0.08040	0.0410*
H42A	−0.19850	−0.20230	−0.06310	0.0850*
H42B	−0.06860	−0.24610	−0.02470	0.0850*
H42C	−0.05080	−0.22930	−0.09580	0.0850*

	U11	U22	U33	U12	U13	U23
S1	0.0235 (2)	0.0238 (2)	0.0199 (2)	−0.0006 (1)	−0.0002 (1)	−0.0011 (1)
O1	0.0348 (6)	0.0278 (6)	0.0350 (6)	−0.0002 (5)	−0.0117 (5)	−0.0044 (5)
O2	0.0365 (6)	0.0277 (5)	0.0250 (5)	−0.0039 (4)	−0.0030 (5)	0.0016 (4)
O3	0.0288 (6)	0.0262 (5)	0.0286 (6)	0.0011 (4)	−0.0055 (4)	0.0035 (4)
N1	0.0253 (6)	0.0225 (6)	0.0230 (6)	0.0015 (5)	−0.0033 (5)	−0.0004 (5)
N2	0.0260 (7)	0.0280 (6)	0.0239 (6)	0.0021 (5)	−0.0021 (5)	−0.0034 (5)
N3	0.0259 (7)	0.0287 (6)	0.0224 (6)	0.0013 (5)	−0.0022 (5)	−0.0040 (5)
C1	0.0225 (7)	0.0253 (7)	0.0203 (7)	0.0018 (5)	0.0012 (5)	−0.0021 (5)
C2	0.0244 (7)	0.0257 (7)	0.0241 (7)	0.0016 (5)	−0.0005 (6)	−0.0020 (6)
C3	0.0209 (7)	0.0244 (7)	0.0229 (7)	0.0003 (5)	0.0031 (6)	−0.0014 (5)
C4	0.0227 (7)	0.0268 (7)	0.0240 (7)	−0.0003 (5)	−0.0006 (6)	−0.0012 (6)
C5	0.0217 (7)	0.0288 (7)	0.0228 (7)	−0.0004 (5)	0.0024 (6)	0.0006 (6)
C6	0.0347 (9)	0.0277 (8)	0.0318 (8)	0.0031 (6)	−0.0025 (7)	0.0054 (6)
C7	0.0268 (8)	0.0212 (7)	0.0235 (7)	0.0003 (5)	−0.0048 (6)	−0.0017 (5)
C8	0.0328 (9)	0.0275 (7)	0.0320 (8)	−0.0003 (6)	0.0056 (7)	−0.0009 (6)
C9	0.0357 (9)	0.0275 (8)	0.0477 (10)	0.0042 (6)	0.0068 (8)	−0.0027 (7)
C10	0.0419 (10)	0.0241 (7)	0.0417 (10)	0.0013 (7)	−0.0053 (8)	0.0029 (7)
C11	0.0494 (11)	0.0340 (9)	0.0335 (9)	−0.0030 (7)	0.0052 (8)	0.0083 (7)
C12	0.0386 (9)	0.0335 (8)	0.0288 (8)	0.0021 (7)	0.0063 (7)	0.0011 (6)
C13	0.0202 (7)	0.0371 (8)	0.0203 (7)	0.0019 (6)	0.0012 (6)	−0.0025 (6)
C14	0.0290 (9)	0.0438 (9)	0.0292 (8)	0.0007 (7)	−0.0052 (7)	0.0053 (7)
C15	0.0202 (7)	0.0394 (8)	0.0237 (7)	0.0007 (6)	0.0009 (6)	−0.0057 (6)
C16	0.0290 (9)	0.0410 (9)	0.0373 (9)	0.0027 (7)	−0.0090 (7)	−0.0070 (7)
C17	0.0321 (9)	0.0367 (9)	0.0505 (11)	0.0038 (7)	−0.0087 (8)	−0.0081 (8)
C18	0.0266 (9)	0.0456 (10)	0.0437 (10)	0.0008 (7)	−0.0006 (7)	−0.0190 (8)
C19	0.0362 (10)	0.0593 (12)	0.0323 (9)	−0.0035 (8)	−0.0091 (8)	−0.0150 (8)
C20	0.0338 (9)	0.0501 (10)	0.0260 (8)	−0.0007 (7)	−0.0061 (7)	−0.0025 (7)
C21	0.0447 (12)	0.0523 (12)	0.0720 (15)	−0.0036 (9)	−0.0093 (11)	−0.0260 (11)
S2	0.0273 (2)	0.0195 (2)	0.0226 (2)	−0.0013 (1)	−0.0010 (1)	−0.0012 (1)
O4	0.0307 (6)	0.0212 (5)	0.0330 (6)	−0.0013 (4)	−0.0072 (5)	−0.0031 (4)
O5	0.0379 (7)	0.0259 (5)	0.0317 (6)	−0.0070 (5)	−0.0066 (5)	0.0031 (4)
O6	0.0309 (6)	0.0226 (5)	0.0301 (6)	−0.0011 (4)	−0.0060 (5)	0.0046 (4)
N4	0.0250 (6)	0.0187 (5)	0.0240 (6)	0.0015 (4)	−0.0021 (5)	−0.0007 (4)
N5	0.0292 (7)	0.0230 (6)	0.0261 (6)	0.0001 (5)	−0.0032 (5)	−0.0021 (5)
N6	0.0297 (7)	0.0224 (6)	0.0257 (6)	0.0007 (5)	−0.0054 (5)	−0.0019 (5)
C22	0.0227 (7)	0.0213 (6)	0.0244 (7)	0.0007 (5)	0.0005 (6)	−0.0026 (5)
C23	0.0218 (7)	0.0207 (6)	0.0237 (7)	0.0016 (5)	0.0012 (5)	−0.0020 (5)
C24	0.0227 (7)	0.0197 (6)	0.0242 (7)	−0.0003 (5)	0.0042 (6)	−0.0025 (5)
C25	0.0231 (7)	0.0222 (7)	0.0232 (7)	−0.0019 (5)	0.0009 (6)	−0.0016 (5)
C26	0.0244 (7)	0.0238 (7)	0.0231 (7)	0.0000 (5)	0.0016 (6)	0.0024 (5)
C27	0.0426 (10)	0.0242 (7)	0.0352 (9)	−0.0027 (6)	−0.0092 (7)	0.0092 (6)
C28	0.0225 (7)	0.0197 (6)	0.0292 (8)	0.0011 (5)	−0.0048 (6)	−0.0001 (5)
C29	0.0295 (8)	0.0274 (7)	0.0354 (9)	0.0036 (6)	−0.0032 (7)	−0.0042 (6)
C30	0.0388 (10)	0.0264 (8)	0.0513 (11)	0.0094 (7)	−0.0116 (8)	−0.0097 (7)
C31	0.0444 (11)	0.0224 (8)	0.0560 (12)	−0.0003 (7)	−0.0201 (9)	0.0070 (7)
C32	0.0421 (10)	0.0363 (9)	0.0437 (10)	−0.0055 (7)	−0.0057 (8)	0.0135 (8)
C33	0.0345 (9)	0.0301 (8)	0.0338 (9)	0.0013 (6)	0.0021 (7)	0.0037 (6)
C34	0.0225 (7)	0.0256 (7)	0.0245 (7)	0.0048 (5)	−0.0021 (6)	−0.0016 (5)
C35	0.0388 (9)	0.0296 (8)	0.0265 (8)	0.0016 (6)	−0.0020 (7)	0.0011 (6)
C36	0.0250 (7)	0.0260 (7)	0.0245 (7)	0.0047 (5)	−0.0042 (6)	−0.0041 (6)
C37	0.0357 (9)	0.0292 (8)	0.0262 (8)	−0.0001 (6)	−0.0049 (7)	−0.0027 (6)
C38	0.0444 (10)	0.0290 (8)	0.0332 (9)	−0.0025 (7)	0.0015 (7)	−0.0020 (7)
C39	0.0358 (9)	0.0330 (8)	0.0379 (9)	−0.0004 (7)	−0.0014 (7)	−0.0134 (7)
C40	0.0418 (10)	0.0393 (9)	0.0352 (9)	0.0051 (7)	−0.0168 (8)	−0.0120 (7)
C41	0.0404 (10)	0.0305 (8)	0.0286 (8)	0.0068 (7)	−0.0105 (7)	−0.0020 (6)
C42	0.0638 (14)	0.0453 (11)	0.0589 (14)	−0.0164 (10)	−0.0026 (11)	−0.0202 (10)

S1—C1	1.7676 (16)	C11—H11	0.9500
S1—C3	1.7460 (15)	C12—H12	0.9500
S2—C22	1.7699 (14)	C14—H14A	0.9800
S2—C24	1.7488 (15)	C14—H14B	0.9800
O1—C2	1.2122 (19)	C14—H14C	0.9800
O2—C5	1.2121 (19)	C16—H16	0.9500
O3—C5	1.3430 (19)	C17—H17	0.9500
O3—C6	1.4503 (19)	C19—H19	0.9500
O4—C23	1.2160 (18)	C20—H20	0.9500
O5—C26	1.2090 (19)	C21—H21B	0.9800
O6—C26	1.3373 (19)	C21—H21C	0.9800
O6—C27	1.4445 (19)	C21—H21A	0.9800
N1—C7	1.4517 (19)	C23—C24	1.4958 (19)
N1—C1	1.390 (2)	C24—C25	1.336 (2)
N1—C2	1.383 (2)	C25—C26	1.472 (2)
N2—C1	1.282 (2)	C28—C29	1.380 (2)
N2—N3	1.4121 (18)	C28—C33	1.382 (2)
N3—C13	1.294 (2)	C29—C30	1.392 (2)
N4—C22	1.3931 (18)	C30—C31	1.381 (3)
N4—C28	1.4419 (17)	C31—C32	1.382 (3)
N4—C23	1.380 (2)	C32—C33	1.387 (2)
N5—C22	1.276 (2)	C34—C35	1.504 (2)
N5—N6	1.4059 (19)	C34—C36	1.487 (2)
N6—C34	1.290 (2)	C36—C37	1.393 (2)
C2—C3	1.501 (2)	C36—C41	1.397 (2)
C3—C4	1.342 (2)	C37—C38	1.389 (2)
C4—C5	1.471 (2)	C38—C39	1.393 (2)
C7—C12	1.384 (2)	C39—C40	1.385 (2)
C7—C8	1.383 (2)	C39—C42	1.507 (3)
C8—C9	1.388 (2)	C40—C41	1.390 (2)
C9—C10	1.380 (2)	C25—H25	0.9500
C10—C11	1.384 (2)	C27—H27A	0.9800
C11—C12	1.388 (2)	C27—H27B	0.9800
C13—C14	1.501 (2)	C27—H27C	0.9800
C13—C15	1.484 (2)	C29—H29	0.9500
C15—C16	1.395 (2)	C30—H30	0.9500
C15—C20	1.398 (2)	C31—H31	0.9500
C16—C17	1.385 (2)	C32—H32	0.9500
C17—C18	1.393 (3)	C33—H33	0.9500
C18—C21	1.511 (3)	C35—H35A	0.9800
C18—C19	1.381 (3)	C35—H35B	0.9800
C19—C20	1.387 (3)	C35—H35C	0.9800
C4—H4	0.9500	C37—H37	0.9500
C6—H6B	0.9800	C38—H38	0.9500
C6—H6C	0.9800	C40—H40	0.9500
C6—H6A	0.9800	C41—H41	0.9500
C8—H8	0.9500	C42—H42A	0.9800
C9—H9	0.9500	C42—H42B	0.9800
C10—H10	0.9500	C42—H42C	0.9800
C1—S1—C3	90.54 (7)	C19—C20—H20	120.00
C22—S2—C24	90.44 (7)	C18—C21—H21A	109.00
C5—O3—C6	115.16 (12)	C18—C21—H21B	109.00
C26—O6—C27	116.03 (12)	C18—C21—H21C	109.00
C2—N1—C7	122.17 (13)	H21A—C21—H21B	109.00
C1—N1—C7	122.00 (12)	H21A—C21—H21C	110.00
C1—N1—C2	115.45 (13)	H21B—C21—H21C	109.00
N3—N2—C1	109.05 (12)	S2—C22—N4	112.14 (10)
N2—N3—C13	114.60 (13)	S2—C22—N5	127.04 (11)
C22—N4—C23	115.76 (11)	N4—C22—N5	120.82 (13)
C23—N4—C28	122.18 (11)	O4—C23—N4	124.89 (12)
C22—N4—C28	122.07 (12)	O4—C23—C24	125.29 (13)
N6—N5—C22	111.28 (12)	N4—C23—C24	109.82 (12)
N5—N6—C34	113.98 (13)	S2—C24—C23	111.77 (10)
S1—C1—N2	125.36 (12)	S2—C24—C25	127.74 (11)
S1—C1—N1	112.54 (11)	C23—C24—C25	120.49 (13)
N1—C1—N2	122.11 (14)	C24—C25—C26	121.26 (13)
O1—C2—N1	124.49 (14)	O5—C26—O6	125.04 (14)
O1—C2—C3	125.59 (14)	O5—C26—C25	123.98 (14)
N1—C2—C3	109.92 (13)	O6—C26—C25	110.97 (13)
S1—C3—C2	111.56 (10)	N4—C28—C29	119.09 (13)
S1—C3—C4	126.95 (11)	N4—C28—C33	119.18 (13)
C2—C3—C4	121.46 (13)	C29—C28—C33	121.73 (13)
C3—C4—C5	120.84 (13)	C28—C29—C30	118.84 (15)
O2—C5—O3	124.16 (14)	C29—C30—C31	119.92 (16)
O2—C5—C4	123.97 (14)	C30—C31—C32	120.57 (16)
O3—C5—C4	111.86 (13)	C31—C32—C33	120.02 (17)
N1—C7—C12	119.78 (13)	C28—C33—C32	118.91 (15)
C8—C7—C12	121.39 (14)	N6—C34—C35	124.61 (14)
N1—C7—C8	118.83 (13)	N6—C34—C36	116.04 (13)
C7—C8—C9	118.82 (15)	C35—C34—C36	119.35 (13)
C8—C9—C10	120.57 (16)	C34—C36—C37	121.08 (14)
C9—C10—C11	119.96 (15)	C34—C36—C41	120.86 (14)
C10—C11—C12	120.32 (16)	C37—C36—C41	118.02 (14)
C7—C12—C11	118.94 (15)	C36—C37—C38	120.91 (15)
N3—C13—C14	124.30 (14)	C37—C38—C39	121.15 (16)
N3—C13—C15	116.33 (13)	C38—C39—C40	117.78 (16)
C14—C13—C15	119.36 (13)	C38—C39—C42	121.62 (16)
C13—C15—C16	121.22 (14)	C40—C39—C42	120.60 (17)
C13—C15—C20	121.17 (15)	C39—C40—C41	121.64 (17)
C16—C15—C20	117.61 (16)	C36—C41—C40	120.49 (16)
C15—C16—C17	120.94 (16)	C24—C25—H25	119.00
C16—C17—C18	121.22 (17)	C26—C25—H25	119.00
C19—C18—C21	121.55 (17)	O6—C27—H27A	109.00
C17—C18—C19	117.95 (17)	O6—C27—H27B	110.00
C17—C18—C21	120.48 (18)	O6—C27—H27C	109.00
C18—C19—C20	121.31 (17)	H27A—C27—H27B	109.00
C15—C20—C19	120.95 (17)	H27A—C27—H27C	109.00
C3—C4—H4	120.00	H27B—C27—H27C	109.00
C5—C4—H4	120.00	C28—C29—H29	121.00
O3—C6—H6A	109.00	C30—C29—H29	121.00
O3—C6—H6B	109.00	C29—C30—H30	120.00
O3—C6—H6C	109.00	C31—C30—H30	120.00
H6A—C6—H6B	110.00	C30—C31—H31	120.00
H6A—C6—H6C	109.00	C32—C31—H31	120.00
H6B—C6—H6C	109.00	C31—C32—H32	120.00
C7—C8—H8	121.00	C33—C32—H32	120.00
C9—C8—H8	121.00	C28—C33—H33	121.00
C10—C9—H9	120.00	C32—C33—H33	121.00
C8—C9—H9	120.00	C34—C35—H35A	109.00
C9—C10—H10	120.00	C34—C35—H35B	109.00
C11—C10—H10	120.00	C34—C35—H35C	109.00
C12—C11—H11	120.00	H35A—C35—H35B	109.00
C10—C11—H11	120.00	H35A—C35—H35C	109.00
C7—C12—H12	121.00	H35B—C35—H35C	110.00
C11—C12—H12	121.00	C36—C37—H37	120.00
C13—C14—H14A	109.00	C38—C37—H37	119.00
C13—C14—H14B	110.00	C37—C38—H38	119.00
C13—C14—H14C	109.00	C39—C38—H38	119.00
H14A—C14—H14B	109.00	C39—C40—H40	119.00
H14A—C14—H14C	109.00	C41—C40—H40	119.00
H14B—C14—H14C	109.00	C36—C41—H41	120.00
C17—C16—H16	120.00	C40—C41—H41	120.00
C15—C16—H16	119.00	C39—C42—H42A	109.00
C16—C17—H17	119.00	C39—C42—H42B	109.00
C18—C17—H17	119.00	C39—C42—H42C	109.00
C20—C19—H19	119.00	H42A—C42—H42B	110.00
C18—C19—H19	119.00	H42A—C42—H42C	109.00
C15—C20—H20	120.00	H42B—C42—H42C	109.00
C3—S1—C1—N1	0.11 (11)	C3—C4—C5—O3	178.91 (14)
C3—S1—C1—N2	−179.71 (14)	N1—C7—C8—C9	−179.64 (15)
C1—S1—C3—C2	−0.07 (11)	C12—C7—C8—C9	0.5 (2)
C1—S1—C3—C4	177.97 (15)	N1—C7—C12—C11	179.59 (14)
C24—S2—C22—N4	−1.44 (11)	C8—C7—C12—C11	−0.5 (2)
C24—S2—C22—N5	178.62 (15)	C7—C8—C9—C10	−0.2 (3)
C22—S2—C24—C23	−0.07 (10)	C8—C9—C10—C11	−0.1 (3)
C22—S2—C24—C25	179.95 (14)	C9—C10—C11—C12	0.0 (3)
C6—O3—C5—C4	176.87 (12)	C10—C11—C12—C7	0.3 (3)
C6—O3—C5—O2	−2.7 (2)	N3—C13—C15—C16	5.6 (2)
C27—O6—C26—C25	177.82 (12)	C14—C13—C15—C20	5.1 (2)
C27—O6—C26—O5	−1.2 (2)	N3—C13—C15—C20	−175.20 (15)
C2—N1—C1—S1	−0.13 (16)	C14—C13—C15—C16	−174.20 (15)
C7—N1—C2—C3	173.02 (13)	C13—C15—C20—C19	−177.58 (15)
C1—N1—C7—C8	90.13 (18)	C13—C15—C16—C17	177.81 (15)
C1—N1—C7—C12	−89.96 (18)	C16—C15—C20—C19	1.7 (2)
C2—N1—C7—C8	−82.35 (19)	C20—C15—C16—C17	−1.5 (2)
C2—N1—C7—C12	97.56 (18)	C15—C16—C17—C18	0.1 (3)
C1—N1—C2—O1	−179.89 (15)	C16—C17—C18—C19	1.0 (3)
C1—N1—C2—C3	0.08 (17)	C16—C17—C18—C21	−177.52 (18)
C7—N1—C2—O1	−7.0 (2)	C21—C18—C19—C20	177.73 (18)
C7—N1—C1—N2	6.8 (2)	C17—C18—C19—C20	−0.8 (3)
C2—N1—C1—N2	179.70 (14)	C18—C19—C20—C15	−0.6 (3)
C7—N1—C1—S1	−173.08 (11)	O4—C23—C24—S2	−178.30 (12)
N3—N2—C1—N1	−178.21 (13)	O4—C23—C24—C25	1.7 (2)
C1—N2—N3—C13	−178.90 (13)	N4—C23—C24—S2	1.55 (15)
N3—N2—C1—S1	1.60 (18)	N4—C23—C24—C25	−178.47 (14)
N2—N3—C13—C14	0.8 (2)	S2—C24—C25—C26	−2.0 (2)
N2—N3—C13—C15	−178.93 (12)	C23—C24—C25—C26	178.07 (13)
C23—N4—C22—N5	−177.30 (14)	C24—C25—C26—O5	−1.4 (2)
C28—N4—C22—S2	−176.83 (11)	C24—C25—C26—O6	179.53 (14)
C23—N4—C22—S2	2.75 (16)	N4—C28—C29—C30	179.08 (14)
C22—N4—C23—O4	177.12 (14)	C33—C28—C29—C30	−0.1 (2)
C22—N4—C23—C24	−2.73 (17)	N4—C28—C33—C32	−178.52 (14)
C28—N4—C23—O4	−3.3 (2)	C29—C28—C33—C32	0.6 (2)
C28—N4—C23—C24	176.84 (12)	C28—C29—C30—C31	−0.1 (2)
C22—N4—C28—C29	110.72 (17)	C29—C30—C31—C32	−0.3 (3)
C22—N4—C28—C33	−70.12 (19)	C30—C31—C32—C33	0.9 (3)
C28—N4—C22—N5	3.1 (2)	C31—C32—C33—C28	−1.0 (3)
C23—N4—C28—C33	110.33 (17)	N6—C34—C36—C37	−6.3 (2)
C23—N4—C28—C29	−68.83 (19)	N6—C34—C36—C41	171.27 (15)
N6—N5—C22—S2	3.38 (19)	C35—C34—C36—C37	174.39 (15)
N6—N5—C22—N4	−176.57 (13)	C35—C34—C36—C41	−8.0 (2)
C22—N5—N6—C34	−165.53 (14)	C34—C36—C37—C38	177.40 (15)
N5—N6—C34—C36	−175.22 (13)	C41—C36—C37—C38	−0.3 (2)
N5—N6—C34—C35	4.0 (2)	C34—C36—C41—C40	−176.81 (15)
O1—C2—C3—C4	1.8 (2)	C37—C36—C41—C40	0.9 (2)
O1—C2—C3—S1	179.97 (14)	C36—C37—C38—C39	−0.7 (3)
N1—C2—C3—S1	0.02 (16)	C37—C38—C39—C40	1.1 (3)
N1—C2—C3—C4	−178.15 (14)	C37—C38—C39—C42	−179.48 (18)
C2—C3—C4—C5	177.02 (14)	C38—C39—C40—C41	−0.5 (3)
S1—C3—C4—C5	−0.8 (2)	C42—C39—C40—C41	−179.92 (18)
C3—C4—C5—O2	−1.5 (2)	C39—C40—C41—C36	−0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O6i	0.95	2.56	3.4802 (19)	163
C6—H6B···O4i	0.98	2.52	3.465 (2)	163
C8—H8···O2ii	0.95	2.56	3.359 (2)	142
C12—H12···O4	0.95	2.43	3.302 (2)	152
C14—H14A···N2	0.98	2.28	2.728 (2)	107
C27—H27B···O1i	0.98	2.45	3.410 (2)	166
C30—H30···O5iii	0.95	2.44	3.331 (2)	157
C32—H32···O1iv	0.95	2.57	3.340 (2)	139
C35—H35A···N5	0.98	2.27	2.718 (2)	106
C33—H33···Cgv	0.95	2.58	3.4951 (19)	162

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C36–C41 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O6i	0.95	2.56	3.4802 (19)	163
C6—H6B⋯O4i	0.98	2.52	3.465 (2)	163
C8—H8⋯O2ii	0.95	2.56	3.359 (2)	142
C12—H12⋯O4	0.95	2.43	3.302 (2)	152
C27—H27B⋯O1i	0.98	2.45	3.410 (2)	166
C30—H30⋯O5iii	0.95	2.44	3.331 (2)	157
C32—H32⋯O1iv	0.95	2.57	3.340 (2)	139
C33—H33⋯Cg v	0.95	2.58	3.4951 (19)	162

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