Ethyl 3-(4-chloro-benzo-yl)-1-(4-chloro-benz-yl)-4-(4-chloro-phen-yl)-2,2-dioxo-3,4,6,7,8,8a-hexa-hydro-1H-pyrrolo-[2,1-c][1,4]thia-zine-1-carboxyl-ate.

In the title compound, C30H28Cl3NO5S, the pyrrolidine ring adopts an envelope conformation (with the N atom as the flap) and the thia-zine ring is in a distorted chair conformation. The mol-ecular structure shows three intra-molecular C-H⋯O inter-actions leading to self-associated ring S(6) and two S(7) motifs. In the crystal, the molecules are linked by C-H⋯O and C-H⋯Cl inter-actions. Two R 2 (2)(10) and one R 2 (2)(16) centrosymmetrically related ring motifs are observed in the unit cell and they are connected through C(6) and C(11) chain motifs extending along the b and c axes, respectively.

Related literature

For the biological and pharmacological properties of thia­zine, pyrrolidine and pyrrolo­thia­zine compounds, see: Armenise et al. (1991 ▶, 1998 ▶); Hemming & Patel (2004 ▶); Koketsu et al. (2002 ▶); Kueh et al. (2003 ▶); Moriyama et al. (2004 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶). For hydrogen-bonding inter­actions, see: Desiraju & Steiner (1999 ▶). For ring and chain motifs,see: Etter et al. (1990 ▶).

Experimental

Crystal data

C30H28Cl3NO5S

M = 620.94

Monoclinic,

a = 14.0476 (8) Å

b = 17.1365 (9) Å

c = 13.8230 (8) Å

β = 115.893 (1)°

V = 2993.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.42 mm−1

T = 293 K

0.25 × 0.21 × 0.19 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

28492 measured reflections

5280 independent reflections

4593 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.144

S = 1.04

5280 reflections

362 parameters

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.47 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL/PC; molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL/PC.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813009148/hg5304sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009148/hg5304Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009148/hg5304Isup3.cml

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

C30H28Cl3NO5S	F(000) = 1288
Mr = 620.94	Dx = 1.378 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2846 reflections
a = 14.0476 (8) Å	θ = 2.1–23.6°
b = 17.1365 (9) Å	µ = 0.42 mm−1
c = 13.8230 (8) Å	T = 293 K
β = 115.893 (1)°	Block, colourless
V = 2993.5 (3) Å3	0.25 × 0.21 × 0.19 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	4593 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
ω scans	h = −16→16
28492 measured reflections	k = −20→20
5280 independent reflections	l = −16→16

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0788P)2 + 1.5863P] where P = (Fo2 + 2Fc2)/3
5280 reflections	(Δ/σ)max < 0.001
362 parameters	Δρmax = 0.62 e Å−3
0 restraints	Δρmin = −0.47 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
C2	0.30396 (17)	0.51264 (12)	0.30011 (17)	0.0434 (5)
H2	0.3262	0.5069	0.3775	0.052*
C3	0.32692 (17)	0.43589 (12)	0.25525 (18)	0.0421 (5)
H3	0.2936	0.4386	0.1765	0.051*
C4	0.52037 (17)	0.51148 (13)	0.28742 (17)	0.0462 (5)
C5	0.47658 (18)	0.57139 (13)	0.34189 (18)	0.0464 (5)
H5	0.4931	0.5526	0.4145	0.056*
C6	0.5171 (2)	0.65580 (14)	0.3507 (2)	0.0581 (6)
H6A	0.5623	0.6692	0.4250	0.070*
H6B	0.5567	0.6626	0.3088	0.070*
C7	0.4188 (3)	0.70537 (18)	0.3067 (4)	0.0956 (12)
H7A	0.4288	0.7520	0.3499	0.115*
H7B	0.4001	0.7206	0.2331	0.115*
C8	0.3344 (2)	0.65402 (14)	0.3125 (2)	0.0639 (7)
H8A	0.3390	0.6528	0.3845	0.077*
H8B	0.2642	0.6709	0.2623	0.077*
C21	0.18549 (17)	0.52703 (12)	0.24388 (18)	0.0451 (5)
C22	0.13824 (19)	0.55639 (15)	0.1399 (2)	0.0539 (6)
H22	0.1798	0.5666	0.1043	0.065*
C23	0.0312 (2)	0.57072 (16)	0.0883 (2)	0.0597 (6)
H23	0.0006	0.5914	0.0192	0.072*
C24	−0.02958 (19)	0.55391 (16)	0.1408 (2)	0.0596 (6)
C25	0.0141 (2)	0.52410 (16)	0.2430 (2)	0.0626 (7)
H25	−0.0283	0.5125	0.2773	0.075*
C26	0.12222 (19)	0.51156 (15)	0.2946 (2)	0.0546 (6)
H26	0.1526	0.4924	0.3646	0.066*
C31	0.27926 (17)	0.36683 (12)	0.29028 (18)	0.0441 (5)
C32	0.22590 (18)	0.30213 (13)	0.21383 (18)	0.0470 (5)
C33	0.1529 (2)	0.25797 (17)	0.2318 (2)	0.0703 (8)
H33	0.1360	0.2714	0.2877	0.084*
C34	0.1049 (3)	0.19463 (18)	0.1685 (3)	0.0780 (9)
H34	0.0551	0.1656	0.1805	0.094*
C35	0.1315 (2)	0.17463 (15)	0.0871 (2)	0.0607 (6)
C36	0.2019 (2)	0.21813 (16)	0.0660 (2)	0.0589 (6)
H36	0.2184	0.2044	0.0099	0.071*
C37	0.24830 (19)	0.28249 (14)	0.12862 (19)	0.0521 (5)
H37	0.2950	0.3130	0.1137	0.062*
C41	0.47985 (19)	0.53106 (14)	0.16841 (19)	0.0514 (5)
C42	0.5045 (3)	0.6192 (2)	0.0487 (2)	0.0892 (10)
H42A	0.4357	0.6440	0.0231	0.107*
H42B	0.5007	0.5780	−0.0010	0.107*
C43	0.5867 (4)	0.6772 (3)	0.0586 (4)	0.1303 (18)
H43A	0.5781	0.7233	0.0934	0.195*
H43B	0.5797	0.6904	−0.0117	0.195*
H43C	0.6556	0.6554	0.1005	0.195*
C44	0.64259 (18)	0.50781 (16)	0.3518 (2)	0.0579 (6)
H44A	0.6707	0.5581	0.3449	0.069*
H44B	0.6589	0.5012	0.4271	0.069*
C45	0.7021 (2)	0.44590 (17)	0.3230 (3)	0.0659 (7)
C46	0.7454 (2)	0.3830 (2)	0.3891 (3)	0.0887 (10)
H46	0.7330	0.3769	0.4495	0.106*
C47	0.8069 (3)	0.3284 (2)	0.3689 (5)	0.1182 (16)
H47	0.8355	0.2863	0.4150	0.142*
C48	0.8248 (3)	0.3370 (3)	0.2819 (5)	0.1174 (18)
C49	0.7820 (3)	0.3981 (3)	0.2116 (5)	0.1128 (15)
H49	0.7937	0.4029	0.1507	0.135*
C50	0.7208 (3)	0.4527 (2)	0.2339 (3)	0.0890 (10)
H50	0.6920	0.4946	0.1874	0.107*
N1	0.36103 (15)	0.57763 (10)	0.28163 (15)	0.0454 (4)
S1	0.46708 (4)	0.41746 (3)	0.30207 (5)	0.04713 (18)
Cl1	−0.16584 (6)	0.56953 (6)	0.07504 (8)	0.0933 (3)
Cl2	0.07475 (7)	0.09158 (5)	0.01151 (8)	0.0880 (3)
Cl3	0.90614 (12)	0.27103 (8)	0.2570 (2)	0.1971 (10)
O1	0.51209 (14)	0.40207 (10)	0.41537 (14)	0.0607 (4)
O2	0.47986 (14)	0.35984 (11)	0.23381 (16)	0.0647 (5)
O3	0.28270 (14)	0.36726 (10)	0.37925 (13)	0.0571 (4)
O41	0.53708 (16)	0.58805 (11)	0.15630 (14)	0.0672 (5)
O42	0.40585 (15)	0.50130 (12)	0.09663 (14)	0.0698 (5)

	U11	U22	U33	U12	U13	U23
C2	0.0436 (11)	0.0422 (11)	0.0471 (11)	−0.0010 (9)	0.0222 (9)	−0.0014 (9)
C3	0.0413 (11)	0.0399 (11)	0.0474 (11)	−0.0022 (9)	0.0215 (9)	−0.0018 (9)
C4	0.0414 (11)	0.0481 (12)	0.0507 (12)	−0.0082 (9)	0.0216 (10)	−0.0057 (9)
C5	0.0440 (12)	0.0467 (12)	0.0465 (12)	−0.0054 (9)	0.0179 (9)	−0.0058 (9)
C6	0.0556 (14)	0.0497 (13)	0.0667 (15)	−0.0133 (11)	0.0247 (12)	−0.0127 (11)
C7	0.0680 (19)	0.0485 (16)	0.148 (3)	−0.0096 (14)	0.027 (2)	0.0009 (18)
C8	0.0571 (15)	0.0415 (12)	0.0856 (18)	0.0015 (11)	0.0243 (13)	−0.0055 (12)
C21	0.0455 (11)	0.0393 (11)	0.0518 (12)	0.0002 (9)	0.0225 (10)	−0.0037 (9)
C22	0.0509 (13)	0.0583 (14)	0.0554 (13)	−0.0026 (11)	0.0259 (11)	−0.0010 (11)
C23	0.0565 (15)	0.0637 (15)	0.0526 (14)	0.0005 (12)	0.0181 (11)	0.0019 (11)
C24	0.0437 (13)	0.0611 (15)	0.0692 (16)	0.0050 (11)	0.0202 (12)	−0.0023 (12)
C25	0.0525 (14)	0.0666 (16)	0.0780 (17)	0.0067 (12)	0.0372 (13)	0.0091 (13)
C26	0.0524 (13)	0.0561 (14)	0.0605 (14)	0.0065 (11)	0.0296 (11)	0.0077 (11)
C31	0.0434 (11)	0.0423 (11)	0.0506 (12)	0.0030 (9)	0.0241 (9)	0.0027 (9)
C32	0.0462 (12)	0.0414 (11)	0.0558 (13)	−0.0014 (9)	0.0245 (10)	0.0004 (9)
C33	0.0788 (19)	0.0686 (17)	0.0830 (18)	−0.0229 (15)	0.0534 (16)	−0.0172 (14)
C34	0.080 (2)	0.0710 (18)	0.099 (2)	−0.0318 (16)	0.0541 (18)	−0.0211 (16)
C35	0.0526 (14)	0.0492 (13)	0.0745 (16)	−0.0042 (11)	0.0224 (12)	−0.0125 (12)
C36	0.0558 (14)	0.0625 (15)	0.0603 (14)	−0.0016 (12)	0.0272 (12)	−0.0124 (12)
C37	0.0509 (13)	0.0534 (13)	0.0568 (13)	−0.0055 (10)	0.0281 (11)	−0.0031 (11)
C41	0.0499 (13)	0.0566 (13)	0.0526 (13)	−0.0084 (11)	0.0269 (11)	−0.0071 (11)
C42	0.117 (3)	0.092 (2)	0.0600 (17)	−0.030 (2)	0.0404 (18)	0.0024 (16)
C43	0.130 (4)	0.126 (4)	0.130 (4)	−0.023 (3)	0.052 (3)	0.046 (3)
C44	0.0408 (12)	0.0670 (16)	0.0617 (14)	−0.0076 (11)	0.0186 (11)	−0.0077 (12)
C45	0.0390 (12)	0.0688 (17)	0.0889 (19)	−0.0104 (12)	0.0270 (13)	−0.0145 (14)
C46	0.0550 (17)	0.085 (2)	0.119 (3)	0.0066 (16)	0.0307 (17)	0.004 (2)
C47	0.064 (2)	0.080 (3)	0.207 (5)	0.0059 (18)	0.055 (3)	−0.001 (3)
C48	0.064 (2)	0.074 (2)	0.235 (6)	−0.0205 (18)	0.084 (3)	−0.046 (3)
C49	0.098 (3)	0.104 (3)	0.180 (5)	−0.026 (2)	0.101 (3)	−0.043 (3)
C50	0.075 (2)	0.090 (2)	0.126 (3)	−0.0059 (17)	0.066 (2)	−0.014 (2)
N1	0.0441 (10)	0.0391 (9)	0.0520 (10)	−0.0027 (7)	0.0200 (8)	−0.0019 (8)
S1	0.0422 (3)	0.0435 (3)	0.0578 (4)	0.0003 (2)	0.0238 (3)	−0.0024 (2)
Cl1	0.0474 (4)	0.1287 (8)	0.0944 (6)	0.0176 (4)	0.0223 (4)	0.0155 (5)
Cl2	0.0776 (5)	0.0677 (5)	0.1101 (7)	−0.0189 (4)	0.0330 (5)	−0.0361 (4)
Cl3	0.1240 (10)	0.1021 (9)	0.429 (3)	−0.0200 (7)	0.1794 (16)	−0.0818 (13)
O1	0.0545 (10)	0.0600 (10)	0.0626 (10)	0.0061 (8)	0.0209 (8)	0.0127 (8)
O2	0.0539 (10)	0.0556 (10)	0.0929 (13)	−0.0025 (8)	0.0398 (9)	−0.0198 (9)
O3	0.0714 (11)	0.0530 (9)	0.0562 (10)	−0.0058 (8)	0.0363 (9)	0.0006 (7)
O41	0.0766 (12)	0.0707 (12)	0.0566 (10)	−0.0256 (10)	0.0314 (9)	−0.0020 (8)
O42	0.0675 (11)	0.0886 (14)	0.0498 (9)	−0.0284 (10)	0.0224 (9)	−0.0113 (9)

C2—N1	1.459 (3)	C32—C33	1.382 (3)
C2—C21	1.518 (3)	C32—C37	1.387 (3)
C2—C3	1.547 (3)	C33—C34	1.372 (4)
C2—H2	0.9800	C33—H33	0.9300
C3—C31	1.538 (3)	C34—C35	1.375 (4)
C3—S1	1.812 (2)	C34—H34	0.9300
C3—H3	0.9800	C35—C36	1.368 (4)
C4—C41	1.525 (3)	C35—Cl2	1.739 (3)
C4—C5	1.551 (3)	C36—C37	1.378 (3)
C4—C44	1.552 (3)	C36—H36	0.9300
C4—S1	1.825 (2)	C37—H37	0.9300
C5—N1	1.469 (3)	C41—O42	1.193 (3)
C5—C6	1.540 (3)	C41—O41	1.321 (3)
C5—H5	0.9800	C42—O41	1.453 (3)
C6—C7	1.505 (4)	C42—C43	1.483 (5)
C6—H6A	0.9700	C42—H42A	0.9700
C6—H6B	0.9700	C42—H42B	0.9700
C7—C8	1.505 (4)	C43—H43A	0.9600
C7—H7A	0.9700	C43—H43B	0.9600
C7—H7B	0.9700	C43—H43C	0.9600
C8—N1	1.475 (3)	C44—C45	1.508 (4)
C8—H8A	0.9700	C44—H44A	0.9700
C8—H8B	0.9700	C44—H44B	0.9700
C21—C26	1.377 (3)	C45—C46	1.372 (5)
C21—C22	1.388 (3)	C45—C50	1.372 (5)
C22—C23	1.376 (4)	C46—C47	1.383 (5)
C22—H22	0.9300	C46—H46	0.9300
C23—C24	1.370 (4)	C47—C48	1.340 (7)
C23—H23	0.9300	C47—H47	0.9300
C24—C25	1.370 (4)	C48—C49	1.375 (7)
C24—Cl1	1.744 (2)	C48—Cl3	1.745 (4)
C25—C26	1.384 (3)	C49—C50	1.393 (5)
C25—H25	0.9300	C49—H49	0.9300
C26—H26	0.9300	C50—H50	0.9300
C31—O3	1.209 (3)	S1—O2	1.4302 (18)
C31—C32	1.489 (3)	S1—O1	1.4343 (18)
N1—C2—C21	110.48 (18)	C37—C32—C31	123.6 (2)
N1—C2—C3	110.62 (17)	C34—C33—C32	120.9 (3)
C21—C2—C3	107.86 (17)	C34—C33—H33	119.5
N1—C2—H2	109.3	C32—C33—H33	119.5
C21—C2—H2	109.3	C33—C34—C35	119.1 (3)
C3—C2—H2	109.3	C33—C34—H34	120.5
C31—C3—C2	109.41 (17)	C35—C34—H34	120.5
C31—C3—S1	107.94 (14)	C36—C35—C34	121.3 (2)
C2—C3—S1	112.91 (14)	C36—C35—Cl2	120.2 (2)
C31—C3—H3	108.8	C34—C35—Cl2	118.6 (2)
C2—C3—H3	108.8	C35—C36—C37	119.3 (2)
S1—C3—H3	108.8	C35—C36—H36	120.3
C41—C4—C5	109.74 (19)	C37—C36—H36	120.3
C41—C4—C44	115.21 (19)	C36—C37—C32	120.5 (2)
C5—C4—C44	108.81 (18)	C36—C37—H37	119.7
C41—C4—S1	109.64 (15)	C32—C37—H37	119.7
C5—C4—S1	105.17 (14)	O42—C41—O41	124.6 (2)
C44—C4—S1	107.77 (17)	O42—C41—C4	125.6 (2)
N1—C5—C6	104.79 (18)	O41—C41—C4	109.77 (19)
N1—C5—C4	110.32 (17)	O41—C42—C43	105.5 (3)
C6—C5—C4	116.68 (19)	O41—C42—H42A	110.6
N1—C5—H5	108.3	C43—C42—H42A	110.6
C6—C5—H5	108.3	O41—C42—H42B	110.6
C4—C5—H5	108.3	C43—C42—H42B	110.6
C7—C6—C5	104.8 (2)	H42A—C42—H42B	108.8
C7—C6—H6A	110.8	C42—C43—H43A	109.5
C5—C6—H6A	110.8	C42—C43—H43B	109.5
C7—C6—H6B	110.8	H43A—C43—H43B	109.5
C5—C6—H6B	110.8	C42—C43—H43C	109.5
H6A—C6—H6B	108.9	H43A—C43—H43C	109.5
C8—C7—C6	104.7 (2)	H43B—C43—H43C	109.5
C8—C7—H7A	110.8	C45—C44—C4	118.6 (2)
C6—C7—H7A	110.8	C45—C44—H44A	107.7
C8—C7—H7B	110.8	C4—C44—H44A	107.7
C6—C7—H7B	110.8	C45—C44—H44B	107.7
H7A—C7—H7B	108.9	C4—C44—H44B	107.7
N1—C8—C7	101.5 (2)	H44A—C44—H44B	107.1
N1—C8—H8A	111.5	C46—C45—C50	117.5 (3)
C7—C8—H8A	111.5	C46—C45—C44	120.8 (3)
N1—C8—H8B	111.5	C50—C45—C44	121.5 (3)
C7—C8—H8B	111.5	C45—C46—C47	122.1 (4)
H8A—C8—H8B	109.3	C45—C46—H46	118.9
C26—C21—C22	118.3 (2)	C47—C46—H46	118.9
C26—C21—C2	121.0 (2)	C48—C47—C46	119.0 (4)
C22—C21—C2	120.7 (2)	C48—C47—H47	120.5
C23—C22—C21	121.4 (2)	C46—C47—H47	120.5
C23—C22—H22	119.3	C47—C48—C49	121.5 (4)
C21—C22—H22	119.3	C47—C48—Cl3	120.0 (5)
C24—C23—C22	118.7 (2)	C49—C48—Cl3	118.5 (5)
C24—C23—H23	120.6	C48—C49—C50	118.5 (4)
C22—C23—H23	120.6	C48—C49—H49	120.7
C23—C24—C25	121.5 (2)	C50—C49—H49	120.7
C23—C24—Cl1	119.2 (2)	C45—C50—C49	121.3 (4)
C25—C24—Cl1	119.4 (2)	C45—C50—H50	119.4
C24—C25—C26	119.1 (2)	C49—C50—H50	119.4
C24—C25—H25	120.5	C2—N1—C5	113.62 (17)
C26—C25—H25	120.5	C2—N1—C8	113.53 (18)
C21—C26—C25	121.0 (2)	C5—N1—C8	104.91 (17)
C21—C26—H26	119.5	O2—S1—O1	118.10 (12)
C25—C26—H26	119.5	O2—S1—C3	108.33 (10)
O3—C31—C32	120.7 (2)	O1—S1—C3	108.31 (10)
O3—C31—C3	119.06 (19)	O2—S1—C4	111.14 (11)
C32—C31—C3	120.19 (19)	O1—S1—C4	106.08 (11)
C33—C32—C37	118.8 (2)	C3—S1—C4	103.94 (10)
C33—C32—C31	117.6 (2)	C41—O41—C42	117.7 (2)
N1—C2—C3—C31	171.76 (17)	S1—C4—C41—O42	17.2 (3)
C21—C2—C3—C31	−67.3 (2)	C5—C4—C41—O41	80.3 (2)
N1—C2—C3—S1	51.5 (2)	C44—C4—C41—O41	−42.9 (3)
C21—C2—C3—S1	172.46 (14)	S1—C4—C41—O41	−164.69 (17)
C41—C4—C5—N1	51.9 (2)	C41—C4—C44—C45	−64.2 (3)
C44—C4—C5—N1	178.80 (18)	C5—C4—C44—C45	172.1 (2)
S1—C4—C5—N1	−66.0 (2)	S1—C4—C44—C45	58.5 (3)
C41—C4—C5—C6	−67.5 (2)	C4—C44—C45—C46	−107.4 (3)
C44—C4—C5—C6	59.4 (3)	C4—C44—C45—C50	76.8 (3)
S1—C4—C5—C6	174.66 (17)	C50—C45—C46—C47	0.8 (5)
N1—C5—C6—C7	7.3 (3)	C44—C45—C46—C47	−175.1 (3)
C4—C5—C6—C7	129.7 (3)	C45—C46—C47—C48	−0.1 (6)
C5—C6—C7—C8	19.4 (3)	C46—C47—C48—C49	−1.0 (6)
C6—C7—C8—N1	−38.9 (3)	C46—C47—C48—Cl3	177.6 (3)
N1—C2—C21—C26	−136.5 (2)	C47—C48—C49—C50	1.4 (6)
C3—C2—C21—C26	102.5 (2)	Cl3—C48—C49—C50	−177.3 (3)
N1—C2—C21—C22	43.3 (3)	C46—C45—C50—C49	−0.4 (5)
C3—C2—C21—C22	−77.7 (2)	C44—C45—C50—C49	175.5 (3)
C26—C21—C22—C23	0.7 (4)	C48—C49—C50—C45	−0.7 (6)
C2—C21—C22—C23	−179.1 (2)	C21—C2—N1—C5	174.57 (17)
C21—C22—C23—C24	−1.3 (4)	C3—C2—N1—C5	−66.1 (2)
C22—C23—C24—C25	0.6 (4)	C21—C2—N1—C8	54.8 (2)
C22—C23—C24—Cl1	−178.4 (2)	C3—C2—N1—C8	174.15 (19)
C23—C24—C25—C26	0.7 (4)	C6—C5—N1—C2	−156.72 (19)
Cl1—C24—C25—C26	179.8 (2)	C4—C5—N1—C2	76.9 (2)
C22—C21—C26—C25	0.7 (4)	C6—C5—N1—C8	−32.1 (2)
C2—C21—C26—C25	−179.5 (2)	C4—C5—N1—C8	−158.5 (2)
C24—C25—C26—C21	−1.4 (4)	C7—C8—N1—C2	168.8 (2)
C2—C3—C31—O3	−37.8 (3)	C7—C8—N1—C5	44.2 (3)
S1—C3—C31—O3	85.4 (2)	C31—C3—S1—O2	75.70 (17)
C2—C3—C31—C32	139.7 (2)	C2—C3—S1—O2	−163.24 (16)
S1—C3—C31—C32	−97.0 (2)	C31—C3—S1—O1	−53.52 (17)
O3—C31—C32—C33	20.7 (3)	C2—C3—S1—O1	67.55 (17)
C3—C31—C32—C33	−156.8 (2)	C31—C3—S1—C4	−166.03 (14)
O3—C31—C32—C37	−157.0 (2)	C2—C3—S1—C4	−44.96 (17)
C3—C31—C32—C37	25.5 (3)	C41—C4—S1—O2	48.18 (19)
C37—C32—C33—C34	1.5 (4)	C5—C4—S1—O2	166.11 (15)
C31—C32—C33—C34	−176.3 (3)	C44—C4—S1—O2	−77.93 (18)
C32—C33—C34—C35	0.9 (5)	C41—C4—S1—O1	177.75 (15)
C33—C34—C35—C36	−2.2 (5)	C5—C4—S1—O1	−64.32 (16)
C33—C34—C35—Cl2	177.0 (3)	C44—C4—S1—O1	51.64 (17)
C34—C35—C36—C37	1.0 (4)	C41—C4—S1—C3	−68.15 (17)
Cl2—C35—C36—C37	−178.2 (2)	C5—C4—S1—C3	49.78 (16)
C35—C36—C37—C32	1.5 (4)	C44—C4—S1—C3	165.74 (15)
C33—C32—C37—C36	−2.7 (4)	O42—C41—O41—C42	3.1 (4)
C31—C32—C37—C36	174.9 (2)	C4—C41—O41—C42	−175.0 (3)
C5—C4—C41—O42	−97.8 (3)	C43—C42—O41—C41	−175.9 (3)
C44—C4—C41—O42	139.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···O41	0.97	2.38	3.051 (3)	126
C37—H37···O2	0.93	2.53	3.213 (3)	131
C50—H50···O41	0.93	2.58	3.282 (4)	132
C6—H6A···O3i	0.97	2.70	3.582 (3)	151
C5—H5···O1i	0.98	2.51	3.320 (3)	140
C8—H8B···Cl3ii	0.97	2.86	3.678 (3)	143
C36—H36···O3iii	0.93	2.65	3.557 (3)	166
C42—H42B···O42iv	0.97	2.61	3.478 (5)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6B⋯O41	0.97	2.38	3.051 (3)	126
C37—H37⋯O2	0.93	2.53	3.213 (3)	131
C50—H50⋯O41	0.93	2.58	3.282 (4)	132
C6—H6A⋯O3i	0.97	2.70	3.582 (3)	151
C5—H5⋯O1i	0.98	2.51	3.320 (3)	140
C8—H8B⋯Cl3ii	0.97	2.86	3.678 (3)	143
C36—H36⋯O3iii	0.93	2.65	3.557 (3)	166
C42—H42B⋯O42iv	0.97	2.61	3.478 (5)	148

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