8-(2-Chloro-phen-yl)-1-(4-chloro-phen-yl)-4-[(E)-(2-chloro-phen-yl)methyl-idene]-6-methyl-4,5,6,7,7a,8-hexa-hydro-1,2,4-oxadiazolo[5,4-d]pyrido[3,4-c][1,5]benzothia-zepine.

In the title compound, C(33)H(26)Cl(3)N(3)OS, the oxadiazole, piperidine and benzothia-pezine rings adopt envelope, chair and twist-boat conformations, respectively. In the crystal, the mol-ecular aggregation is characterized by chains of centrosymmetrically related pairs connected through Cl⋯Cl inter-actions [3.533 (2) Å], extending parallel to (202).

Related literature

For the biological importance of benziothia­zepines and oxadiazol derivatives, see: Budriesi et al. (2007 ▶); Sahin et al. (2002 ▶). For ring geometry, see: Boeyens (1978 ▶); Cremer & Pople (1975 ▶). For a related structure, see: Srinivasan et al. (2007 ▶).

Experimental

Crystal data

C33H26Cl3N3OS

M = 618.98

Triclinic,

a = 11.015 (3) Å

b = 11.758 (4) Å

c = 11.988 (4) Å

α = 78.87 (2)°

β = 86.89 (3)°

γ = 78.29 (2)°

V = 1491.5 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.41 mm−1

T = 298 K

0.30 × 0.15 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.90, T max = 0.94

42055 measured reflections

11096 independent reflections

7867 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.146

S = 1.03

11096 reflections

372 parameters

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −0.62 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810013309/nc2178sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013309/nc2178Isup2.hkl

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

C33H26Cl3N3OS	Z = 2
Mr = 618.98	F(000) = 640
Triclinic, P1	Dx = 1.378 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.015 (3) Å	Cell parameters from 4125 reflections
b = 11.758 (4) Å	θ = 2.0–30.0°
c = 11.988 (4) Å	µ = 0.41 mm−1
α = 78.87 (2)°	T = 298 K
β = 86.89 (3)°	Needle, colourless
γ = 78.29 (2)°	0.30 × 0.15 × 0.15 mm
V = 1491.5 (8) Å3

Bruker Kappa APEXII CCD diffractometer	11096 independent reflections
Radiation source: fine-focus sealed tube	7867 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω and φ scan	θmax = 33.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −16→16
Tmin = 0.90, Tmax = 0.94	k = −17→17
42055 measured reflections	l = −18→18

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) = 0.146	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0605P)2 + 0.6302P] where P = (Fo2 + 2Fc2)/3
11096 reflections	(Δ/σ)max = 0.001
372 parameters	Δρmax = 0.64 e Å−3
0 restraints	Δρmin = −0.62 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Cl1	0.57470 (7)	−0.12556 (6)	1.22882 (7)	0.0878 (2)
Cl2	0.55422 (5)	0.34566 (6)	0.58843 (6)	0.07294 (17)
Cl3	0.71901 (7)	0.77874 (5)	0.53545 (4)	0.0769 (2)
C1	0.85278 (14)	0.22540 (11)	0.96401 (12)	0.0336 (3)
N2	0.97082 (12)	0.20144 (11)	0.95229 (12)	0.0404 (3)
O3	1.00715 (9)	0.30577 (9)	0.89247 (9)	0.0378 (2)
C3A	0.89581 (12)	0.37735 (11)	0.83332 (11)	0.0300 (2)
C4	0.89945 (13)	0.33994 (11)	0.71870 (12)	0.0320 (3)
C5	1.01522 (14)	0.36089 (13)	0.65093 (13)	0.0368 (3)
H5A	1.0857	0.3030	0.6843	0.044*
H5B	1.0069	0.3495	0.5739	0.044*
N6	1.03901 (12)	0.48001 (11)	0.64726 (10)	0.0353 (2)
C7	1.03493 (13)	0.51369 (13)	0.75868 (13)	0.0355 (3)
H7A	1.0489	0.5938	0.7497	0.043*
H7B	1.1005	0.4617	0.8053	0.043*
C7A	0.90965 (12)	0.50621 (11)	0.81809 (12)	0.0307 (2)
H71A	0.9104	0.5276	0.8931	0.037*
C8	0.80644 (13)	0.59400 (11)	0.74674 (12)	0.0315 (2)
H8	0.8252	0.5869	0.6672	0.038*
S9	0.65096 (3)	0.56089 (3)	0.77852 (3)	0.03747 (9)
C9A	0.65984 (13)	0.52634 (12)	0.92758 (13)	0.0333 (3)
C10	0.59577 (15)	0.60462 (13)	0.99383 (16)	0.0439 (3)
H10	0.5521	0.6780	0.9589	0.053*
C11	0.59637 (17)	0.57444 (16)	1.11118 (17)	0.0484 (4)
H11	0.5521	0.6266	1.1549	0.058*
C12	0.66289 (16)	0.46670 (16)	1.16287 (14)	0.0437 (3)
H12	0.6613	0.4453	1.2417	0.052*
C13	0.73233 (14)	0.38968 (13)	1.09826 (13)	0.0368 (3)
H13	0.7803	0.3188	1.1340	0.044*
C13A	0.73021 (12)	0.41847 (11)	0.98022 (12)	0.0303 (2)
N14	0.79641 (11)	0.34047 (9)	0.91010 (10)	0.0300 (2)
C61	1.15951 (16)	0.48759 (16)	0.59264 (15)	0.0462 (4)
H61A	1.1759	0.5652	0.5899	0.069*
H61B	1.1591	0.4726	0.5168	0.069*
H61C	1.2229	0.4299	0.6354	0.069*
C1E	0.78313 (14)	0.13884 (11)	1.02695 (12)	0.0350 (3)
C2E	0.65779 (16)	0.15047 (14)	1.01121 (16)	0.0458 (4)
H2E	0.6168	0.2127	0.9579	0.055*
C3E	0.59237 (19)	0.07021 (16)	1.07412 (19)	0.0555 (5)
H3E	0.5074	0.0796	1.0650	0.067*
C4E	0.6548 (2)	−0.02356 (15)	1.15020 (17)	0.0527 (4)
C5E	0.7800 (2)	−0.03845 (15)	1.16498 (16)	0.0529 (4)
H5E	0.8211	−0.1032	1.2156	0.063*
C6E	0.84464 (17)	0.04309 (13)	1.10441 (14)	0.0443 (3)
H6E	0.9293	0.0341	1.1153	0.053*
C40	0.80948 (15)	0.29252 (12)	0.68793 (12)	0.0364 (3)
H40	0.7441	0.2867	0.7398	0.044*
C41	0.79968 (17)	0.24807 (13)	0.58271 (13)	0.0419 (3)
C42	0.9013 (2)	0.18426 (17)	0.53161 (17)	0.0557 (5)
H42	0.9788	0.1682	0.5647	0.067*
C43	0.8879 (3)	0.1446 (2)	0.4319 (2)	0.0757 (7)
H43	0.9568	0.1037	0.3980	0.091*
C44	0.7738 (3)	0.1654 (2)	0.38322 (19)	0.0815 (8)
H44	0.7656	0.1387	0.3164	0.098*
C45	0.6718 (3)	0.2253 (2)	0.43257 (18)	0.0690 (6)
H45	0.5942	0.2383	0.4002	0.083*
C46	0.68514 (19)	0.26646 (16)	0.53113 (15)	0.0503 (4)
C81	0.80119 (13)	0.72208 (12)	0.75331 (12)	0.0336 (3)
C82	0.82787 (18)	0.75779 (14)	0.85131 (15)	0.0460 (4)
H82	0.8572	0.7006	0.9140	0.055*
C83	0.8122 (2)	0.87629 (16)	0.85885 (19)	0.0585 (5)
H83	0.8297	0.8974	0.9262	0.070*
C84	0.7708 (2)	0.96217 (16)	0.7669 (2)	0.0635 (5)
H84	0.7607	1.0416	0.7717	0.076*
C85	0.7445 (2)	0.93064 (15)	0.66774 (18)	0.0598 (5)
H85	0.7168	0.9885	0.6050	0.072*
C86	0.75923 (17)	0.81224 (14)	0.66168 (14)	0.0436 (3)

	U11	U22	U33	U12	U13	U23
Cl1	0.1016 (5)	0.0606 (3)	0.0984 (5)	−0.0388 (3)	0.0198 (4)	0.0104 (3)
Cl2	0.0590 (3)	0.0861 (4)	0.0774 (4)	−0.0188 (3)	−0.0099 (3)	−0.0169 (3)
Cl3	0.1281 (5)	0.0532 (3)	0.0411 (2)	0.0047 (3)	−0.0262 (3)	−0.0051 (2)
C1	0.0396 (7)	0.0255 (5)	0.0314 (6)	0.0003 (5)	0.0013 (5)	−0.0025 (5)
N2	0.0403 (6)	0.0324 (6)	0.0411 (7)	0.0011 (5)	0.0000 (5)	0.0022 (5)
O3	0.0318 (5)	0.0364 (5)	0.0399 (5)	−0.0018 (4)	−0.0024 (4)	0.0015 (4)
C3A	0.0312 (6)	0.0271 (5)	0.0302 (6)	−0.0029 (4)	−0.0011 (5)	−0.0043 (4)
C4	0.0377 (7)	0.0256 (5)	0.0318 (6)	−0.0046 (5)	0.0018 (5)	−0.0054 (4)
C5	0.0399 (7)	0.0343 (6)	0.0366 (7)	−0.0070 (5)	0.0049 (6)	−0.0091 (5)
N6	0.0375 (6)	0.0350 (6)	0.0335 (6)	−0.0097 (5)	0.0018 (5)	−0.0044 (4)
C7	0.0357 (7)	0.0349 (6)	0.0371 (7)	−0.0096 (5)	−0.0016 (5)	−0.0067 (5)
C7A	0.0334 (6)	0.0278 (5)	0.0314 (6)	−0.0065 (5)	−0.0025 (5)	−0.0055 (5)
C8	0.0366 (6)	0.0276 (5)	0.0303 (6)	−0.0060 (5)	−0.0027 (5)	−0.0048 (4)
S9	0.03504 (17)	0.03241 (16)	0.0429 (2)	−0.00581 (13)	−0.00816 (14)	−0.00064 (13)
C9A	0.0302 (6)	0.0275 (6)	0.0415 (7)	−0.0045 (5)	0.0010 (5)	−0.0063 (5)
C10	0.0401 (8)	0.0306 (6)	0.0599 (10)	−0.0017 (6)	0.0067 (7)	−0.0133 (6)
C11	0.0483 (9)	0.0447 (8)	0.0581 (10)	−0.0099 (7)	0.0122 (8)	−0.0266 (8)
C12	0.0472 (8)	0.0509 (9)	0.0387 (8)	−0.0146 (7)	0.0045 (6)	−0.0187 (7)
C13	0.0387 (7)	0.0368 (7)	0.0357 (7)	−0.0069 (5)	−0.0009 (5)	−0.0092 (5)
C13A	0.0294 (6)	0.0271 (5)	0.0349 (6)	−0.0046 (4)	0.0007 (5)	−0.0080 (5)
N14	0.0330 (5)	0.0231 (4)	0.0310 (5)	−0.0016 (4)	0.0021 (4)	−0.0031 (4)
C61	0.0456 (8)	0.0512 (9)	0.0429 (8)	−0.0179 (7)	0.0091 (7)	−0.0052 (7)
C1E	0.0426 (7)	0.0238 (5)	0.0351 (7)	−0.0006 (5)	0.0046 (5)	−0.0046 (5)
C2E	0.0457 (8)	0.0315 (7)	0.0553 (10)	−0.0037 (6)	−0.0005 (7)	−0.0006 (6)
C3E	0.0514 (10)	0.0409 (8)	0.0724 (13)	−0.0125 (7)	0.0056 (9)	−0.0042 (8)
C4E	0.0684 (12)	0.0340 (7)	0.0553 (10)	−0.0164 (7)	0.0136 (9)	−0.0042 (7)
C5E	0.0704 (12)	0.0319 (7)	0.0474 (9)	−0.0029 (7)	0.0042 (8)	0.0057 (6)
C6E	0.0503 (9)	0.0322 (7)	0.0434 (8)	0.0006 (6)	0.0012 (7)	0.0006 (6)
C40	0.0456 (8)	0.0308 (6)	0.0342 (7)	−0.0119 (5)	0.0033 (6)	−0.0062 (5)
C41	0.0631 (10)	0.0334 (7)	0.0341 (7)	−0.0221 (7)	0.0032 (7)	−0.0061 (5)
C42	0.0753 (13)	0.0449 (9)	0.0521 (10)	−0.0158 (9)	0.0077 (9)	−0.0201 (8)
C43	0.118 (2)	0.0592 (12)	0.0582 (13)	−0.0252 (13)	0.0204 (14)	−0.0288 (10)
C44	0.141 (3)	0.0757 (15)	0.0429 (11)	−0.0470 (17)	0.0015 (14)	−0.0220 (10)
C45	0.1051 (18)	0.0694 (13)	0.0436 (10)	−0.0437 (13)	−0.0145 (11)	−0.0061 (9)
C46	0.0713 (12)	0.0456 (8)	0.0402 (8)	−0.0299 (8)	−0.0033 (8)	−0.0028 (7)
C81	0.0385 (7)	0.0273 (5)	0.0346 (7)	−0.0064 (5)	−0.0007 (5)	−0.0051 (5)
C82	0.0612 (10)	0.0329 (7)	0.0447 (8)	−0.0057 (7)	−0.0120 (7)	−0.0100 (6)
C83	0.0764 (13)	0.0389 (8)	0.0653 (12)	−0.0070 (8)	−0.0167 (10)	−0.0223 (8)
C84	0.0848 (15)	0.0293 (7)	0.0776 (14)	−0.0098 (8)	−0.0056 (11)	−0.0131 (8)
C85	0.0850 (14)	0.0296 (7)	0.0580 (11)	−0.0053 (8)	−0.0037 (10)	0.0032 (7)
C86	0.0584 (10)	0.0328 (7)	0.0365 (7)	−0.0057 (6)	−0.0010 (7)	−0.0022 (5)

Cl1—C4E	1.7345 (19)	C13A—N14	1.4279 (17)
Cl2—C46	1.736 (2)	C61—H61A	0.9600
Cl3—C86	1.7364 (19)	C61—H61B	0.9600
C1—N2	1.279 (2)	C61—H61C	0.9600
C1—N14	1.4138 (17)	C1E—C2E	1.379 (2)
C1—C1E	1.467 (2)	C1E—C6E	1.394 (2)
N2—O3	1.4169 (17)	C2E—C3E	1.386 (3)
O3—C3A	1.4698 (17)	C2E—H2E	0.9300
C3A—N14	1.4708 (18)	C3E—C4E	1.376 (3)
C3A—C4	1.518 (2)	C3E—H3E	0.9300
C3A—C7A	1.5285 (19)	C4E—C5E	1.371 (3)
C4—C40	1.331 (2)	C5E—C6E	1.381 (2)
C4—C5	1.511 (2)	C5E—H5E	0.9300
C5—N6	1.4684 (19)	C6E—H6E	0.9300
C5—H5A	0.9700	C40—C41	1.472 (2)
C5—H5B	0.9700	C40—H40	0.9300
N6—C61	1.459 (2)	C41—C46	1.394 (3)
N6—C7	1.461 (2)	C41—C42	1.398 (3)
C7—C7A	1.529 (2)	C42—C43	1.389 (3)
C7—H7A	0.9700	C42—H42	0.9300
C7—H7B	0.9700	C43—C44	1.372 (4)
C7A—C8	1.5420 (19)	C43—H43	0.9300
C7A—H71A	0.9800	C44—C45	1.370 (4)
C8—C81	1.5124 (19)	C44—H44	0.9300
C8—S9	1.8364 (16)	C45—C46	1.386 (3)
C8—H8	0.9800	C45—H45	0.9300
S9—C9A	1.7580 (17)	C81—C82	1.386 (2)
C9A—C10	1.391 (2)	C81—C86	1.397 (2)
C9A—C13A	1.3974 (19)	C82—C83	1.389 (2)
C10—C11	1.383 (3)	C82—H82	0.9300
C10—H10	0.9300	C83—C84	1.371 (3)
C11—C12	1.377 (3)	C83—H83	0.9300
C11—H11	0.9300	C84—C85	1.373 (3)
C12—C13	1.389 (2)	C84—H84	0.9300
C12—H12	0.9300	C85—C86	1.384 (2)
C13—C13A	1.390 (2)	C85—H85	0.9300
C13—H13	0.9300
N2—C1—N14	114.41 (13)	N6—C61—H61A	109.5
N2—C1—C1E	122.05 (12)	N6—C61—H61B	109.5
N14—C1—C1E	123.53 (13)	H61A—C61—H61B	109.5
C1—N2—O3	106.95 (11)	N6—C61—H61C	109.5
N2—O3—C3A	105.63 (10)	H61A—C61—H61C	109.5
O3—C3A—N14	101.63 (10)	H61B—C61—H61C	109.5
O3—C3A—C4	105.55 (10)	C2E—C1E—C6E	119.32 (15)
N14—C3A—C4	113.86 (11)	C2E—C1E—C1	121.26 (13)
O3—C3A—C7A	106.44 (11)	C6E—C1E—C1	119.43 (15)
N14—C3A—C7A	117.54 (11)	C1E—C2E—C3E	120.60 (16)
C4—C3A—C7A	110.41 (11)	C1E—C2E—H2E	119.7
C40—C4—C5	126.87 (13)	C3E—C2E—H2E	119.7
C40—C4—C3A	121.26 (13)	C4E—C3E—C2E	119.13 (19)
C5—C4—C3A	111.85 (12)	C4E—C3E—H3E	120.4
N6—C5—C4	112.64 (11)	C2E—C3E—H3E	120.4
N6—C5—H5A	109.1	C5E—C4E—C3E	121.18 (16)
C4—C5—H5A	109.1	C5E—C4E—Cl1	119.05 (15)
N6—C5—H5B	109.1	C3E—C4E—Cl1	119.77 (17)
C4—C5—H5B	109.1	C4E—C5E—C6E	119.72 (16)
H5A—C5—H5B	107.8	C4E—C5E—H5E	120.1
C61—N6—C7	109.80 (12)	C6E—C5E—H5E	120.1
C61—N6—C5	108.88 (12)	C5E—C6E—C1E	120.02 (17)
C7—N6—C5	113.90 (11)	C5E—C6E—H6E	120.0
N6—C7—C7A	110.94 (12)	C1E—C6E—H6E	120.0
N6—C7—H7A	109.5	C4—C40—C41	128.64 (14)
C7A—C7—H7A	109.5	C4—C40—H40	115.7
N6—C7—H7B	109.5	C41—C40—H40	115.7
C7A—C7—H7B	109.5	C46—C41—C42	117.06 (16)
H7A—C7—H7B	108.0	C46—C41—C40	120.18 (16)
C3A—C7A—C7	106.66 (11)	C42—C41—C40	122.74 (17)
C3A—C7A—C8	113.68 (11)	C43—C42—C41	120.8 (2)
C7—C7A—C8	109.23 (12)	C43—C42—H42	119.6
C3A—C7A—H71A	109.1	C41—C42—H42	119.6
C7—C7A—H71A	109.1	C44—C43—C42	120.4 (2)
C8—C7A—H71A	109.1	C44—C43—H43	119.8
C81—C8—C7A	114.25 (11)	C42—C43—H43	119.8
C81—C8—S9	108.47 (10)	C45—C44—C43	120.3 (2)
C7A—C8—S9	113.89 (10)	C45—C44—H44	119.9
C81—C8—H8	106.6	C43—C44—H44	119.9
C7A—C8—H8	106.6	C44—C45—C46	119.5 (2)
S9—C8—H8	106.6	C44—C45—H45	120.3
C9A—S9—C8	98.49 (6)	C46—C45—H45	120.3
C10—C9A—C13A	119.60 (14)	C45—C46—C41	122.0 (2)
C10—C9A—S9	120.58 (12)	C45—C46—Cl2	117.89 (18)
C13A—C9A—S9	119.82 (11)	C41—C46—Cl2	120.09 (14)
C11—C10—C9A	120.63 (15)	C82—C81—C86	116.15 (14)
C11—C10—H10	119.7	C82—C81—C8	122.89 (13)
C9A—C10—H10	119.7	C86—C81—C8	120.79 (13)
C12—C11—C10	119.64 (15)	C81—C82—C83	122.09 (16)
C12—C11—H11	120.2	C81—C82—H82	119.0
C10—C11—H11	120.2	C83—C82—H82	119.0
C11—C12—C13	120.55 (16)	C84—C83—C82	119.96 (18)
C11—C12—H12	119.7	C84—C83—H83	120.0
C13—C12—H12	119.7	C82—C83—H83	120.0
C12—C13—C13A	120.05 (14)	C83—C84—C85	119.84 (17)
C12—C13—H13	120.0	C83—C84—H84	120.1
C13A—C13—H13	120.0	C85—C84—H84	120.1
C13—C13A—C9A	119.41 (13)	C84—C85—C86	119.65 (17)
C13—C13A—N14	122.17 (12)	C84—C85—H85	120.2
C9A—C13A—N14	118.41 (13)	C86—C85—H85	120.2
C1—N14—C13A	117.65 (11)	C85—C86—C81	122.31 (16)
C1—N14—C3A	102.39 (10)	C85—C86—Cl3	117.21 (14)
C13A—N14—C3A	119.70 (11)	C81—C86—Cl3	120.46 (12)
N14—C1—N2—O3	3.72 (17)	C9A—C13A—N14—C3A	63.38 (17)
C1E—C1—N2—O3	−177.20 (13)	O3—C3A—N14—C1	−26.29 (12)
C1—N2—O3—C3A	−21.41 (15)	C4—C3A—N14—C1	86.69 (13)
N2—O3—C3A—N14	29.51 (12)	C7A—C3A—N14—C1	−141.96 (12)
N2—O3—C3A—C4	−89.57 (12)	O3—C3A—N14—C13A	105.95 (12)
N2—O3—C3A—C7A	153.08 (11)	C4—C3A—N14—C13A	−141.07 (12)
O3—C3A—C4—C40	119.11 (14)	C7A—C3A—N14—C13A	−9.72 (17)
N14—C3A—C4—C40	8.51 (18)	N2—C1—C1E—C2E	−160.17 (16)
C7A—C3A—C4—C40	−126.24 (14)	N14—C1—C1E—C2E	18.8 (2)
O3—C3A—C4—C5	−59.56 (14)	N2—C1—C1E—C6E	20.0 (2)
N14—C3A—C4—C5	−170.17 (11)	N14—C1—C1E—C6E	−161.01 (14)
C7A—C3A—C4—C5	55.08 (14)	C6E—C1E—C2E—C3E	2.1 (3)
C40—C4—C5—N6	132.87 (15)	C1—C1E—C2E—C3E	−177.78 (16)
C3A—C4—C5—N6	−48.55 (16)	C1E—C2E—C3E—C4E	−2.0 (3)
C4—C5—N6—C61	173.08 (13)	C2E—C3E—C4E—C5E	0.3 (3)
C4—C5—N6—C7	50.17 (17)	C2E—C3E—C4E—Cl1	−179.47 (16)
C61—N6—C7—C7A	−179.84 (12)	C3E—C4E—C5E—C6E	1.3 (3)
C5—N6—C7—C7A	−57.44 (16)	Cl1—C4E—C5E—C6E	−178.92 (15)
O3—C3A—C7A—C7	53.94 (13)	C4E—C5E—C6E—C1E	−1.2 (3)
N14—C3A—C7A—C7	166.95 (11)	C2E—C1E—C6E—C5E	−0.4 (2)
C4—C3A—C7A—C7	−60.14 (14)	C1—C1E—C6E—C5E	179.41 (15)
O3—C3A—C7A—C8	174.39 (11)	C5—C4—C40—C41	0.6 (3)
N14—C3A—C7A—C8	−72.60 (15)	C3A—C4—C40—C41	−177.89 (14)
C4—C3A—C7A—C8	60.30 (15)	C4—C40—C41—C46	−141.76 (17)
N6—C7—C7A—C3A	61.13 (14)	C4—C40—C41—C42	39.8 (2)
N6—C7—C7A—C8	−62.13 (14)	C46—C41—C42—C43	1.9 (3)
C3A—C7A—C8—C81	166.54 (12)	C40—C41—C42—C43	−179.61 (17)
C7—C7A—C8—C81	−74.47 (14)	C41—C42—C43—C44	−1.4 (3)
C3A—C7A—C8—S9	41.12 (14)	C42—C43—C44—C45	−0.1 (4)
C7—C7A—C8—S9	160.11 (9)	C43—C44—C45—C46	1.0 (4)
C81—C8—S9—C9A	−85.63 (10)	C44—C45—C46—C41	−0.5 (3)
C7A—C8—S9—C9A	42.81 (11)	C44—C45—C46—Cl2	178.16 (17)
C8—S9—C9A—C10	106.47 (13)	C42—C41—C46—C45	−1.0 (2)
C8—S9—C9A—C13A	−74.58 (12)	C40—C41—C46—C45	−179.52 (16)
C13A—C9A—C10—C11	−3.0 (2)	C42—C41—C46—Cl2	−179.57 (13)
S9—C9A—C10—C11	175.92 (13)	C40—C41—C46—Cl2	1.9 (2)
C9A—C10—C11—C12	1.2 (3)	C7A—C8—C81—C82	−35.1 (2)
C10—C11—C12—C13	2.0 (3)	S9—C8—C81—C82	93.14 (16)
C11—C12—C13—C13A	−3.2 (2)	C7A—C8—C81—C86	149.96 (14)
C12—C13—C13A—C9A	1.3 (2)	S9—C8—C81—C86	−81.81 (16)
C12—C13—C13A—N14	−177.72 (13)	C86—C81—C82—C83	0.9 (3)
C10—C9A—C13A—C13	1.8 (2)	C8—C81—C82—C83	−174.28 (18)
S9—C9A—C13A—C13	−177.20 (11)	C81—C82—C83—C84	−1.0 (3)
C10—C9A—C13A—N14	−179.17 (13)	C82—C83—C84—C85	0.3 (4)
S9—C9A—C13A—N14	1.87 (17)	C83—C84—C85—C86	0.3 (4)
N2—C1—N14—C13A	−118.19 (14)	C84—C85—C86—C81	−0.4 (3)
C1E—C1—N14—C13A	62.74 (18)	C84—C85—C86—Cl3	177.80 (18)
N2—C1—N14—C3A	15.27 (16)	C82—C81—C86—C85	−0.2 (3)
C1E—C1—N14—C3A	−163.80 (13)	C8—C81—C86—C85	175.07 (17)
C13—C13A—N14—C1	7.71 (19)	C82—C81—C86—Cl3	−178.35 (14)
C9A—C13A—N14—C1	−171.33 (12)	C8—C81—C86—Cl3	−3.1 (2)
C13—C13A—N14—C3A	−117.57 (15)