(2SR,3RS)-Methyl 2-(adamantan-1-yl)-3-phenyl-sulfonyl-3-(pyridin-2-ylsulfan-yl)propano-ate dichloro-methane hemisolvate.

The title compound, C(25)H(29)NO(4)S(2) 0.5CH(2)Cl(2), was obtained as a racemate. The pyridine and phenyl rings are arranged face-to-face, giving a weak intra-molecular π-π inter-action [centroid-centroid separation = 3.759 (3) Å]. These inter-actions are extended inter-molecularly, forming chains of stacked rings along [001] with separations of 3.859 (3) and 3.916 (3) Å. The solvent used for crystallization, CH(2)Cl(2), is located in voids between the chains of mol-ecules, with a site occupancy of 0.5.

Related literature

For chemical, polymer and pharmaceutical applications of adamantane and its derivatives, see: Beller et al. (2002 ▶); Mathias et al. (1995 ▶, 2001 ▶); Stotskaya et al. (1995 ▶); Spasov et al. (2000 ▶); Enomoto et al. (2010 ▶). For catalyst reactions, see: Taoufik et al. (1999 ▶). For poly(p-phenyl­ene­vinyl­ene) (PPV) derivatives, see: Jeong et al. (2002 ▶). For their anti­viral and disease-related activity, see: Kadi et al. (2010 ▶); Papanastasiou et al. (2010 ▶) and for their use in the treatment of influenza A, leukemia and deafness, see: Zarubaev et al. (2010 ▶); Spasov et al. (2000 ▶). For the Barton deca­rboxylation reaction, see: Togo (2004 ▶).

Experimental

Crystal data

C25H29NO4S2·0.5CH2Cl2

M = 514.08

Monoclinic,

a = 12.709 (4) Å

b = 27.820 (6) Å

c = 14.448 (3) Å

β = 101.254 (19)°

V = 5010 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.35 mm−1

T = 298 K

0.40 × 0.40 × 0.40 mm

Data collection

Siemens P4 diffractometer

6603 measured reflections

4434 independent reflections

2936 reflections with I > 2σ(I)

R int = 0.026

3 standard reflections every 97 reflections intensity decay: 40%

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.154

S = 1.03

4434 reflections

316 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.31 e Å−3

Data collection: XSCANS (Siemens, 1996 ▶); cell refinement: XSCANS; data reduction: XSCANS; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811010312/jj2070sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010312/jj2070Isup2.hkl

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

C25H29NO4S2·0.5CH2Cl2	F(000) = 2168
Mr = 514.08	Dx = 1.363 Mg m−3
Monoclinic, C2/c	Melting point: 418 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 12.709 (4) Å	Cell parameters from 78 reflections
b = 27.820 (6) Å	θ = 4.8–12.4°
c = 14.448 (3) Å	µ = 0.35 mm−1
β = 101.254 (19)°	T = 298 K
V = 5010 (2) Å3	Irregular, colourless
Z = 8	0.40 × 0.40 × 0.40 mm

Siemens P4 diffractometer	Rint = 0.026
Radiation source: fine-focus sealed tube, FN4	θmax = 25.1°, θmin = 1.8°
graphite	h = −15→4
2θ/ω scans	k = −33→33
6603 measured reflections	l = −17→17
4434 independent reflections	3 standard reflections every 97 reflections
2936 reflections with I > 2σ(I)	intensity decay: 40%

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0607P)2 + 7.2667P] where P = (Fo2 + 2Fc2)/3
4434 reflections	(Δ/σ)max < 0.001
316 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.31 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.17793 (7)	0.34186 (3)	0.15045 (6)	0.0583 (3)
S2	0.17440 (7)	0.32202 (3)	−0.05013 (6)	0.0564 (3)
N1	−0.0193 (2)	0.36197 (12)	−0.1021 (2)	0.0697 (8)
O1	0.3954 (2)	0.35456 (12)	−0.0133 (3)	0.1005 (11)
O2	0.44844 (18)	0.38921 (10)	0.1263 (2)	0.0777 (8)
O3	0.1643 (3)	0.38017 (10)	0.21275 (18)	0.0860 (9)
O4	0.2695 (2)	0.31153 (10)	0.1755 (2)	0.0830 (8)
C1	0.3772 (3)	0.37941 (13)	0.0485 (3)	0.0607 (9)
C2	0.2724 (2)	0.40456 (11)	0.0484 (2)	0.0475 (7)
H2A	0.2785	0.4182	0.1117	0.057*
C3	0.1791 (2)	0.36853 (11)	0.0372 (2)	0.0465 (7)
H3A	0.1127	0.3871	0.0198	0.056*
C4	0.5495 (3)	0.36437 (17)	0.1363 (4)	0.1094 (19)
H4A	0.5953	0.3738	0.1944	0.164*
H4B	0.5831	0.3724	0.0843	0.164*
H4C	0.5374	0.3303	0.1368	0.164*
C5	0.2526 (2)	0.44789 (11)	−0.0205 (2)	0.0490 (8)
C6	0.2242 (5)	0.43425 (15)	−0.1234 (3)	0.0962 (15)
H6A	0.1620	0.4133	−0.1340	0.115*
H6B	0.2835	0.4169	−0.1411	0.115*
C7	0.1992 (6)	0.48093 (18)	−0.1860 (3)	0.125 (2)
H7A	0.1770	0.4725	−0.2528	0.150*
C8	0.1119 (5)	0.5102 (2)	−0.1524 (6)	0.131 (3)
H8A	0.0969	0.5390	−0.1906	0.157*
H8B	0.0465	0.4914	−0.1604	0.157*
C9	0.1435 (3)	0.52322 (17)	−0.0573 (5)	0.1054 (18)
H9A	0.0858	0.5420	−0.0387	0.126*
C10	0.2416 (3)	0.55331 (14)	−0.0445 (4)	0.0905 (14)
H10A	0.2590	0.5649	0.0199	0.109*
H10D	0.2290	0.5809	−0.0863	0.109*
C11	0.3329 (3)	0.52465 (13)	−0.0658 (3)	0.0745 (12)
H11A	0.3979	0.5444	−0.0543	0.089*
C12	0.3515 (3)	0.48017 (12)	−0.0043 (3)	0.0668 (10)
H12A	0.3687	0.4897	0.0615	0.080*
H12B	0.4121	0.4624	−0.0185	0.080*
C13	0.3074 (5)	0.50983 (18)	−0.1689 (4)	0.1148 (19)
H13A	0.3647	0.4899	−0.1836	0.138*
H13B	0.3004	0.5380	−0.2091	0.138*
C14	0.1612 (3)	0.47823 (15)	0.0025 (4)	0.0888 (14)
H14A	0.0958	0.4593	−0.0082	0.107*
H14B	0.1776	0.4872	0.0686	0.107*
C15	0.0612 (3)	0.30632 (12)	0.1304 (2)	0.0502 (8)
C16	0.0685 (3)	0.25765 (13)	0.1145 (3)	0.0624 (9)
H16A	0.1348	0.2432	0.1162	0.075*
C17	−0.0236 (4)	0.23100 (14)	0.0963 (3)	0.0764 (11)
H17A	−0.0204	0.1981	0.0860	0.092*
C18	−0.1212 (3)	0.25308 (18)	0.0932 (3)	0.0794 (12)
H18A	−0.1837	0.2349	0.0800	0.095*
C19	−0.1273 (3)	0.30086 (17)	0.1089 (3)	0.0772 (11)
H19A	−0.1937	0.3152	0.1071	0.093*
C20	−0.0357 (3)	0.32805 (14)	0.1276 (3)	0.0646 (9)
H20A	−0.0395	0.3609	0.1382	0.077*
C21	0.0357 (3)	0.32124 (13)	−0.0982 (2)	0.0543 (8)
C22	−0.0087 (3)	0.27858 (15)	−0.1342 (3)	0.0731 (11)
H22A	0.0319	0.2505	−0.1279	0.088*
C23	−0.1137 (4)	0.2781 (2)	−0.1794 (3)	0.0878 (13)
H23A	−0.1452	0.2498	−0.2055	0.105*
C24	−0.1705 (3)	0.3188 (2)	−0.1856 (3)	0.0879 (14)
H24A	−0.2418	0.3192	−0.2168	0.105*
C25	−0.1224 (3)	0.36013 (18)	−0.1453 (3)	0.0842 (13)
H25A	−0.1634	0.3880	−0.1483	0.101*
Cl1	0.4213 (8)	0.5932 (4)	0.1685 (5)	0.185 (4)	0.50
Cl2	0.5855 (5)	0.6034 (3)	0.3296 (5)	0.146 (3)	0.50
C26	0.5288 (10)	0.6258 (4)	0.2308 (9)	0.117 (4)	0.50
H26A	0.5822	0.6291	0.1915	0.141*	0.50
H26B	0.5038	0.6578	0.2421	0.141*	0.50

	U11	U22	U33	U12	U13	U23
S1	0.0626 (5)	0.0619 (6)	0.0460 (5)	−0.0173 (4)	−0.0003 (4)	0.0039 (4)
S2	0.0525 (5)	0.0586 (5)	0.0574 (5)	−0.0086 (4)	0.0087 (4)	−0.0117 (4)
N1	0.0573 (18)	0.071 (2)	0.072 (2)	−0.0139 (16)	−0.0071 (15)	0.0036 (16)
O1	0.0538 (16)	0.102 (2)	0.142 (3)	0.0152 (15)	0.0085 (17)	−0.038 (2)
O2	0.0442 (13)	0.0790 (18)	0.097 (2)	−0.0072 (12)	−0.0189 (13)	0.0219 (15)
O3	0.126 (2)	0.0806 (18)	0.0551 (15)	−0.0426 (17)	0.0268 (15)	−0.0229 (14)
O4	0.0597 (15)	0.090 (2)	0.0858 (19)	−0.0064 (14)	−0.0193 (13)	0.0332 (16)
C1	0.0431 (18)	0.051 (2)	0.082 (3)	−0.0051 (16)	−0.0023 (18)	0.0075 (19)
C2	0.0397 (16)	0.0519 (18)	0.0468 (17)	−0.0052 (14)	−0.0015 (13)	−0.0003 (14)
C3	0.0434 (16)	0.0497 (18)	0.0430 (17)	−0.0056 (14)	0.0002 (13)	−0.0015 (14)
C4	0.045 (2)	0.084 (3)	0.181 (5)	0.002 (2)	−0.023 (3)	0.037 (3)
C5	0.0362 (15)	0.0476 (18)	0.059 (2)	−0.0061 (13)	0.0002 (14)	0.0027 (15)
C6	0.151 (4)	0.071 (3)	0.058 (2)	−0.037 (3)	−0.001 (3)	0.009 (2)
C7	0.230 (7)	0.073 (3)	0.059 (3)	−0.062 (4)	−0.005 (4)	0.013 (2)
C8	0.104 (4)	0.076 (3)	0.180 (6)	−0.026 (3)	−0.054 (4)	0.042 (4)
C9	0.047 (2)	0.079 (3)	0.183 (6)	0.008 (2)	0.006 (3)	0.038 (4)
C10	0.076 (3)	0.056 (2)	0.133 (4)	0.006 (2)	0.005 (3)	0.021 (2)
C11	0.049 (2)	0.055 (2)	0.114 (3)	−0.0093 (17)	0.001 (2)	0.020 (2)
C12	0.0418 (18)	0.055 (2)	0.095 (3)	−0.0078 (16)	−0.0066 (17)	0.015 (2)
C13	0.168 (5)	0.078 (3)	0.112 (4)	−0.002 (3)	0.058 (4)	0.032 (3)
C14	0.055 (2)	0.072 (3)	0.142 (4)	0.010 (2)	0.027 (2)	0.028 (3)
C15	0.0538 (19)	0.055 (2)	0.0416 (17)	−0.0116 (16)	0.0084 (14)	0.0016 (15)
C16	0.064 (2)	0.054 (2)	0.069 (2)	−0.0032 (18)	0.0145 (18)	0.0095 (18)
C17	0.096 (3)	0.057 (2)	0.079 (3)	−0.023 (2)	0.026 (2)	−0.002 (2)
C18	0.069 (3)	0.099 (3)	0.073 (3)	−0.034 (2)	0.022 (2)	−0.002 (2)
C19	0.059 (2)	0.096 (3)	0.081 (3)	−0.007 (2)	0.024 (2)	−0.005 (2)
C20	0.067 (2)	0.063 (2)	0.067 (2)	−0.0033 (19)	0.0208 (18)	−0.0039 (18)
C21	0.0552 (19)	0.068 (2)	0.0389 (17)	−0.0183 (18)	0.0073 (14)	−0.0029 (16)
C22	0.074 (2)	0.075 (3)	0.071 (2)	−0.027 (2)	0.014 (2)	−0.020 (2)
C23	0.079 (3)	0.102 (4)	0.080 (3)	−0.039 (3)	0.010 (2)	−0.025 (3)
C24	0.063 (3)	0.135 (4)	0.060 (2)	−0.040 (3)	−0.0044 (19)	0.001 (3)
C25	0.058 (2)	0.100 (3)	0.086 (3)	−0.011 (2)	−0.008 (2)	0.011 (3)
Cl1	0.187 (7)	0.233 (7)	0.133 (5)	−0.043 (5)	0.022 (4)	−0.097 (5)
Cl2	0.101 (3)	0.159 (4)	0.154 (5)	0.051 (3)	−0.035 (3)	−0.050 (4)
C26	0.111 (11)	0.150 (9)	0.096 (9)	0.013 (7)	0.029 (6)	0.009 (7)

S1—O4	1.426 (3)	C10—H10D	0.9700
S1—O3	1.427 (3)	C11—C12	1.515 (5)
S1—C15	1.759 (3)	C11—C13	1.518 (7)
S1—C3	1.799 (3)	C11—H11A	0.9800
S2—C21	1.764 (3)	C12—H12A	0.9700
S2—C3	1.800 (3)	C12—H12B	0.9700
N1—C21	1.327 (5)	C13—H13A	0.9700
N1—C25	1.338 (5)	C13—H13B	0.9700
O1—C1	1.187 (5)	C14—H14A	0.9700
O2—C1	1.326 (4)	C14—H14B	0.9700
O2—C4	1.440 (5)	C15—C20	1.366 (5)
C1—C2	1.505 (5)	C15—C16	1.379 (5)
C2—C3	1.537 (4)	C16—C17	1.367 (5)
C2—C5	1.552 (4)	C16—H16A	0.9300
C2—H2A	0.9800	C17—C18	1.376 (6)
C3—H3A	0.9800	C17—H17A	0.9300
C4—H4A	0.9600	C18—C19	1.353 (6)
C4—H4B	0.9600	C18—H18A	0.9300
C4—H4C	0.9600	C19—C20	1.370 (5)
C5—C6	1.508 (5)	C19—H19A	0.9300
C5—C14	1.524 (5)	C20—H20A	0.9300
C5—C12	1.526 (4)	C21—C22	1.372 (5)
C6—C7	1.579 (6)	C22—C23	1.366 (6)
C6—H6A	0.9700	C22—H22A	0.9300
C6—H6B	0.9700	C23—C24	1.337 (6)
C7—C8	1.530 (9)	C23—H23A	0.9300
C7—C13	1.570 (8)	C24—C25	1.376 (6)
C7—H7A	0.9800	C24—H24A	0.9300
C8—C9	1.401 (9)	C25—H25A	0.9300
C8—H8A	0.9700	Cl1—C26i	1.726 (14)
C8—H8B	0.9700	Cl1—C26	1.737 (15)
C9—C10	1.483 (6)	Cl2—C26	1.594 (14)
C9—C14	1.513 (6)	Cl2—C26i	1.663 (15)
C9—H9A	0.9800	C26—H26A	0.9700
C10—C11	1.488 (6)	C26—H26B	0.9700
C10—H10A	0.9700
O4—S1—O3	118.38 (18)	H10A—C10—H10D	108.2
O4—S1—C15	109.21 (16)	C10—C11—C12	110.8 (4)
O3—S1—C15	108.75 (17)	C10—C11—C13	108.8 (4)
O4—S1—C3	108.91 (16)	C12—C11—C13	109.4 (4)
O3—S1—C3	106.81 (16)	C10—C11—H11A	109.2
C15—S1—C3	103.79 (14)	C12—C11—H11A	109.2
C21—S2—C3	100.30 (16)	C13—C11—H11A	109.2
C21—N1—C25	116.5 (3)	C11—C12—C5	111.2 (3)
C1—O2—C4	115.7 (4)	C11—C12—H12A	109.4
O1—C1—O2	123.8 (3)	C5—C12—H12A	109.4
O1—C1—C2	124.9 (3)	C11—C12—H12B	109.4
O2—C1—C2	111.3 (3)	C5—C12—H12B	109.4
C1—C2—C3	111.2 (3)	H12A—C12—H12B	108.0
C1—C2—C5	113.2 (3)	C11—C13—C7	107.8 (4)
C3—C2—C5	114.4 (2)	C11—C13—H13A	110.1
C1—C2—H2A	105.7	C7—C13—H13A	110.1
C3—C2—H2A	105.7	C11—C13—H13B	110.1
C5—C2—H2A	105.7	C7—C13—H13B	110.1
C2—C3—S1	108.4 (2)	H13A—C13—H13B	108.5
C2—C3—S2	117.5 (2)	C9—C14—C5	111.6 (4)
S1—C3—S2	109.63 (17)	C9—C14—H14A	109.3
C2—C3—H3A	106.9	C5—C14—H14A	109.3
S1—C3—H3A	106.9	C9—C14—H14B	109.3
S2—C3—H3A	106.9	C5—C14—H14B	109.3
O2—C4—H4A	109.5	H14A—C14—H14B	108.0
O2—C4—H4B	109.5	C20—C15—C16	121.2 (3)
H4A—C4—H4B	109.5	C20—C15—S1	118.9 (3)
O2—C4—H4C	109.5	C16—C15—S1	119.9 (3)
H4A—C4—H4C	109.5	C17—C16—C15	118.8 (4)
H4B—C4—H4C	109.5	C17—C16—H16A	120.6
C6—C5—C14	108.0 (3)	C15—C16—H16A	120.6
C6—C5—C12	109.3 (3)	C16—C17—C18	119.7 (4)
C14—C5—C12	106.3 (3)	C16—C17—H17A	120.1
C6—C5—C2	114.5 (3)	C18—C17—H17A	120.1
C14—C5—C2	109.0 (3)	C19—C18—C17	120.9 (4)
C12—C5—C2	109.5 (2)	C19—C18—H18A	119.5
C5—C6—C7	109.9 (3)	C17—C18—H18A	119.5
C5—C6—H6A	109.7	C18—C19—C20	120.0 (4)
C7—C6—H6A	109.7	C18—C19—H19A	120.0
C5—C6—H6B	109.7	C20—C19—H19A	120.0
C7—C6—H6B	109.7	C15—C20—C19	119.2 (4)
H6A—C6—H6B	108.2	C15—C20—H20A	120.4
C8—C7—C13	110.1 (4)	C19—C20—H20A	120.4
C8—C7—C6	109.5 (5)	N1—C21—C22	123.2 (3)
C13—C7—C6	105.0 (5)	N1—C21—S2	118.9 (2)
C8—C7—H7A	110.7	C22—C21—S2	117.7 (3)
C13—C7—H7A	110.7	C23—C22—C21	118.8 (4)
C6—C7—H7A	110.7	C23—C22—H22A	120.6
C9—C8—C7	111.2 (4)	C21—C22—H22A	120.6
C9—C8—H8A	109.4	C24—C23—C22	119.2 (4)
C7—C8—H8A	109.4	C24—C23—H23A	120.4
C9—C8—H8B	109.4	C22—C23—H23A	120.4
C7—C8—H8B	109.4	C23—C24—C25	119.4 (4)
H8A—C8—H8B	108.0	C23—C24—H24A	120.3
C8—C9—C10	109.9 (5)	C25—C24—H24A	120.3
C8—C9—C14	109.2 (5)	N1—C25—C24	122.9 (5)
C10—C9—C14	111.6 (4)	N1—C25—H25A	118.6
C8—C9—H9A	108.7	C24—C25—H25A	118.6
C10—C9—H9A	108.7	Cl2—C26—Cl1	115.6 (7)
C14—C9—H9A	108.7	Cl2—C26—H26A	108.4
C9—C10—C11	110.0 (4)	Cl1—C26—H26A	108.4
C9—C10—H10A	109.7	Cl2—C26—H26B	108.4
C11—C10—H10A	109.7	Cl1—C26—H26B	108.4
C9—C10—H10D	109.7	H26A—C26—H26B	107.4
C11—C10—H10D	109.7
C4—O2—C1—O1	−5.1 (5)	C14—C5—C12—C11	−58.7 (4)
C4—O2—C1—C2	176.1 (3)	C2—C5—C12—C11	−176.3 (3)
O1—C1—C2—C3	57.9 (5)	C10—C11—C13—C7	−57.4 (5)
O2—C1—C2—C3	−123.3 (3)	C12—C11—C13—C7	63.9 (5)
O1—C1—C2—C5	−72.6 (5)	C8—C7—C13—C11	53.4 (6)
O2—C1—C2—C5	106.2 (3)	C6—C7—C13—C11	−64.3 (5)
C1—C2—C3—S1	80.7 (3)	C8—C9—C14—C5	63.4 (5)
C5—C2—C3—S1	−149.4 (2)	C10—C9—C14—C5	−58.3 (6)
C1—C2—C3—S2	−44.2 (3)	C6—C5—C14—C9	−59.5 (5)
C5—C2—C3—S2	85.6 (3)	C12—C5—C14—C9	57.7 (5)
O4—S1—C3—C2	−69.3 (2)	C2—C5—C14—C9	175.6 (4)
O3—S1—C3—C2	59.7 (3)	O4—S1—C15—C20	164.6 (3)
C15—S1—C3—C2	174.5 (2)	O3—S1—C15—C20	34.1 (3)
O4—S1—C3—S2	60.2 (2)	C3—S1—C15—C20	−79.3 (3)
O3—S1—C3—S2	−170.85 (17)	O4—S1—C15—C16	−17.7 (3)
C15—S1—C3—S2	−56.0 (2)	O3—S1—C15—C16	−148.2 (3)
C21—S2—C3—C2	−138.9 (2)	C3—S1—C15—C16	98.3 (3)
C21—S2—C3—S1	96.70 (18)	C20—C15—C16—C17	−0.4 (5)
C1—C2—C5—C6	73.5 (4)	S1—C15—C16—C17	−178.0 (3)
C3—C2—C5—C6	−55.4 (4)	C15—C16—C17—C18	0.7 (6)
C1—C2—C5—C14	−165.5 (3)	C16—C17—C18—C19	−0.7 (6)
C3—C2—C5—C14	65.6 (4)	C17—C18—C19—C20	0.5 (6)
C1—C2—C5—C12	−49.7 (4)	C16—C15—C20—C19	0.2 (5)
C3—C2—C5—C12	−178.5 (3)	S1—C15—C20—C19	177.9 (3)
C14—C5—C6—C7	55.1 (5)	C18—C19—C20—C15	−0.3 (6)
C12—C5—C6—C7	−60.2 (5)	C25—N1—C21—C22	−1.3 (5)
C2—C5—C6—C7	176.6 (4)	C25—N1—C21—S2	175.3 (3)
C5—C6—C7—C8	−54.8 (6)	C3—S2—C21—N1	32.5 (3)
C5—C6—C7—C13	63.5 (6)	C3—S2—C21—C22	−150.6 (3)
C13—C7—C8—C9	−56.3 (6)	N1—C21—C22—C23	2.5 (6)
C6—C7—C8—C9	58.7 (5)	S2—C21—C22—C23	−174.2 (3)
C7—C8—C9—C10	60.8 (5)	C21—C22—C23—C24	−1.3 (6)
C7—C8—C9—C14	−61.9 (5)	C22—C23—C24—C25	−0.8 (7)
C8—C9—C10—C11	−65.1 (5)	C21—N1—C25—C24	−1.0 (6)
C14—C9—C10—C11	56.2 (6)	C23—C24—C25—N1	2.1 (7)
C9—C10—C11—C12	−57.0 (5)	Cl1i—Cl2—C26—Cl1	13 (4)
C9—C10—C11—C13	63.4 (5)	C26i—Cl2—C26—Cl1	−62.4 (9)
C10—C11—C12—C5	60.2 (5)	Cl2i—Cl1—C26—Cl2	127 (3)
C13—C11—C12—C5	−59.8 (5)	C26i—Cl1—C26—Cl2	64.3 (11)
C6—C5—C12—C11	57.6 (4)