(R)-[1-(2-Chloro-phen-yl)-2-meth-oxy-2-oxoeth-yl][2-(thio-phen-2-yl)eth-yl]ammonium (+)-camphor-10-sulfonate acetone monosolvate.

The title compound, C(15)H(17)ClNO(2)S(+)·C(10)H(15)O(4)S(-)·C(3)H(6)O, was synthesized by N-alkyl-ation of α-amino-(2-chloro-phen-yl)acetate with 2-thienylethyl p-toluene-sulfonate, followed by reaction with (+)-camphor-10-sulfonic acid. In the crystal, the cations and anions are linked through N-H⋯O hydrogen bonds. The thio-phene ring of the cation was found to be disordered over two sites, with refined occupancies of 0.798 (4) and 0.202 (4).

Related literature

For background to the anti­platelet agent clopidogrel, see: Kang et al. (2007 ▶). For the preparation of the title compound, an inter­mediate of clopidogrel, see: Descamps & Radisson (1992 ▶). For a database of bond lengths and angles, see: Bruno et al. (2004 ▶).

Experimental

Crystal data

C15H17ClNO2S+·C10H15O4S−·C3H6O

M = 600.16

Orthorhombic,

a = 12.101 (3) Å

b = 14.209 (4) Å

c = 18.325 (5) Å

V = 3150.7 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 294 K

0.26 × 0.24 × 0.20 mm

Data collection

Bruker SMART-CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.912, T max = 0.943

18154 measured reflections

6435 independent reflections

4010 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.096

S = 0.99

6435 reflections

402 parameters

70 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 2828 Friedel pairs

Flack parameter: −0.04 (6)

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681004523X/bh2318sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004523X/bh2318Isup2.hkl

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

C15H17ClNO2S+·C10H15O4S−·C3H6O	Dx = 1.265 Mg m−3
Mr = 600.16	Melting point: 368 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4370 reflections
a = 12.101 (3) Å	θ = 2.2–23.4°
b = 14.209 (4) Å	µ = 0.30 mm−1
c = 18.325 (5) Å	T = 294 K
V = 3150.7 (14) Å3	Block, colourless
Z = 4	0.26 × 0.24 × 0.20 mm
F(000) = 1272

Bruker SMART-CCD area-detector diffractometer	6435 independent reflections
Radiation source: fine-focus sealed tube	4010 reflections with I > 2σ(I)
graphite	Rint = 0.039
φ and ω scans	θmax = 26.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→15
Tmin = 0.912, Tmax = 0.943	k = −17→17
18154 measured reflections	l = −13→22

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0457P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.003
6435 reflections	Δρmax = 0.17 e Å−3
402 parameters	Δρmin = −0.18 e Å−3
70 restraints	Absolute structure: Flack (1983), 2828 Friedel pairs
0 constraints	Flack parameter: −0.04 (6)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.41386 (6)	0.37358 (5)	0.48307 (4)	0.0722 (2)
S2	0.77423 (6)	0.77371 (5)	0.58832 (4)	0.04884 (18)
O1	0.60127 (19)	0.69806 (14)	0.40519 (11)	0.0766 (6)
O2	0.62818 (19)	0.55299 (14)	0.36419 (11)	0.0779 (7)
O3	0.65698 (14)	0.75282 (13)	0.58489 (10)	0.0617 (5)
O4	0.83735 (15)	0.72491 (13)	0.53212 (9)	0.0610 (5)
O5	0.79800 (15)	0.87314 (12)	0.58933 (11)	0.0653 (5)
O6	0.6787 (2)	0.60281 (18)	0.75506 (17)	0.1049 (9)
N1	0.4941 (2)	0.64436 (14)	0.52533 (12)	0.0421 (5)
S1	0.40689 (11)	0.62354 (14)	0.78089 (8)	0.0841 (6)	0.798 (4)
C1	0.2895 (5)	0.5925 (5)	0.8266 (3)	0.0692 (18)	0.798 (4)
H1	0.2888	0.5652	0.8727	0.083*	0.798 (4)
C2	0.1991 (5)	0.6124 (5)	0.7880 (3)	0.0622 (16)	0.798 (4)
H2	0.1275	0.6025	0.8047	0.075*	0.798 (4)
C3	0.2257 (5)	0.6518 (10)	0.7158 (5)	0.0578 (19)	0.798 (4)
H3	0.1731	0.6706	0.6819	0.069*	0.798 (4)
C4	0.3347 (2)	0.65728 (18)	0.70495 (14)	0.0510 (7)	0.798 (4)
S1'	0.1970 (7)	0.6383 (13)	0.7155 (7)	0.082 (3)	0.202 (4)
C1'	0.2174 (16)	0.594 (2)	0.8011 (11)	0.058 (8)	0.202 (4)
H1'	0.1667	0.5567	0.8258	0.069*	0.202 (4)
C2'	0.3154 (17)	0.6201 (16)	0.8281 (7)	0.050 (6)	0.202 (4)
H2'	0.3368	0.6123	0.8765	0.060*	0.202 (4)
C3'	0.3863 (12)	0.6634 (16)	0.7701 (6)	0.077 (8)	0.202 (4)
H3'	0.4553	0.6904	0.7777	0.092*	0.202 (4)
C4'	0.3347 (2)	0.65728 (18)	0.70495 (14)	0.0510 (7)	0.202 (4)
C5	0.3906 (2)	0.69093 (18)	0.63647 (15)	0.0569 (7)
H5A	0.4520	0.7316	0.6494	0.068*
H5B	0.3387	0.7276	0.6079	0.068*
C6	0.4329 (2)	0.60951 (17)	0.59081 (14)	0.0534 (7)
H6A	0.4816	0.5707	0.6202	0.064*
H6B	0.3712	0.5709	0.5752	0.064*
C7	0.5266 (2)	0.56885 (16)	0.47250 (14)	0.0444 (6)
H7	0.4588	0.5425	0.4517	0.053*
C8	0.5905 (2)	0.61535 (19)	0.41131 (14)	0.0496 (6)
C9	0.6918 (3)	0.5885 (2)	0.30261 (18)	0.0890 (12)
H9A	0.6464	0.6296	0.2738	0.133*
H9B	0.7162	0.5367	0.2731	0.133*
H9C	0.7548	0.6226	0.3203	0.133*
C10	0.5895 (2)	0.48914 (16)	0.50914 (14)	0.0430 (6)
C11	0.6942 (2)	0.50530 (19)	0.53687 (16)	0.0614 (8)
H11	0.7251	0.5650	0.5332	0.074*
C12	0.7536 (3)	0.4337 (2)	0.56997 (18)	0.0763 (10)
H12	0.8237	0.4456	0.5886	0.092*
C13	0.7088 (3)	0.3454 (2)	0.5751 (2)	0.0829 (10)
H13	0.7489	0.2975	0.5974	0.100*
C14	0.6057 (3)	0.3269 (2)	0.54794 (18)	0.0684 (9)
H14	0.5760	0.2666	0.5513	0.082*
C15	0.5459 (2)	0.39861 (18)	0.51539 (14)	0.0506 (7)
C16	0.8220 (2)	0.7252 (2)	0.67130 (14)	0.0610 (7)
H16A	0.8147	0.6573	0.6679	0.073*
H16B	0.9004	0.7388	0.6750	0.073*
C17	0.7675 (2)	0.75628 (18)	0.74299 (13)	0.0502 (7)
C18	0.6771 (3)	0.8337 (2)	0.74243 (16)	0.0683 (9)
H18A	0.6980	0.8854	0.7107	0.082*
H18B	0.6068	0.8084	0.7262	0.082*
C19	0.6703 (3)	0.8666 (3)	0.82296 (18)	0.0803 (10)
H19A	0.6923	0.9319	0.8279	0.096*
H19B	0.5963	0.8587	0.8423	0.096*
C20	0.7528 (3)	0.8007 (3)	0.86121 (17)	0.0772 (10)
H20	0.7777	0.8227	0.9092	0.093*
C21	0.8457 (2)	0.7907 (2)	0.80388 (15)	0.0661 (8)
C22	0.9343 (3)	0.7182 (3)	0.8242 (2)	0.1106 (14)
H22A	0.9014	0.6568	0.8268	0.166*
H22B	0.9657	0.7341	0.8707	0.166*
H22C	0.9913	0.7182	0.7877	0.166*
C23	0.9031 (3)	0.8840 (3)	0.7847 (2)	0.1080 (13)
H23A	0.9479	0.9039	0.8250	0.162*
H23B	0.8483	0.9311	0.7746	0.162*
H23C	0.9488	0.8753	0.7424	0.162*
C24	0.7097 (3)	0.6759 (3)	0.7821 (2)	0.0713 (8)
C25	0.7012 (3)	0.7047 (3)	0.86146 (19)	0.0928 (11)
H25A	0.6247	0.7072	0.8773	0.111*
H25B	0.7417	0.6617	0.8927	0.111*
O7	0.5385 (3)	1.09004 (19)	0.51597 (19)	0.1357 (12)
C26	0.5766 (4)	0.9442 (3)	0.4603 (2)	0.1191 (15)
H26A	0.5182	0.9098	0.4369	0.179*
H26B	0.6277	0.9008	0.4821	0.179*
H26C	0.6145	0.9819	0.4248	0.179*
C27	0.5296 (3)	1.0056 (2)	0.5173 (2)	0.0789 (10)
C28	0.4691 (3)	0.9580 (3)	0.5765 (2)	0.0971 (12)
H28A	0.4356	1.0042	0.6077	0.146*
H28B	0.5195	0.9202	0.6045	0.146*
H28C	0.4127	0.9184	0.5560	0.146*
H1A	0.451 (2)	0.6847 (18)	0.5023 (14)	0.051 (8)*
H1B	0.558 (3)	0.676 (2)	0.5390 (16)	0.074 (10)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0766 (5)	0.0706 (5)	0.0693 (5)	−0.0249 (4)	0.0075 (4)	−0.0046 (4)
S2	0.0504 (4)	0.0544 (4)	0.0417 (4)	−0.0062 (3)	0.0027 (3)	−0.0028 (3)
O1	0.1156 (17)	0.0536 (12)	0.0607 (13)	−0.0068 (11)	0.0315 (13)	0.0019 (10)
O2	0.1170 (17)	0.0568 (12)	0.0599 (13)	0.0153 (12)	0.0358 (13)	0.0003 (11)
O3	0.0508 (10)	0.0817 (14)	0.0527 (11)	−0.0132 (10)	0.0003 (10)	−0.0086 (11)
O4	0.0678 (11)	0.0693 (11)	0.0459 (10)	−0.0107 (10)	0.0147 (10)	−0.0115 (10)
O5	0.0747 (12)	0.0535 (11)	0.0677 (12)	−0.0128 (10)	0.0109 (11)	−0.0007 (10)
O6	0.0981 (19)	0.0734 (16)	0.143 (3)	−0.0087 (14)	0.0256 (17)	−0.0057 (16)
N1	0.0442 (13)	0.0422 (12)	0.0399 (13)	0.0020 (11)	0.0032 (11)	0.0029 (11)
S1	0.0663 (8)	0.1282 (14)	0.0576 (7)	0.0092 (9)	−0.0056 (6)	0.0178 (8)
C1	0.079 (4)	0.076 (5)	0.052 (3)	−0.006 (3)	0.004 (3)	0.015 (2)
C2	0.060 (3)	0.067 (3)	0.060 (3)	0.022 (3)	0.019 (2)	0.018 (3)
C3	0.056 (4)	0.068 (4)	0.049 (3)	−0.010 (4)	0.003 (3)	0.023 (2)
C4	0.0581 (18)	0.0524 (16)	0.0424 (17)	0.0046 (13)	0.0077 (14)	−0.0041 (13)
S1'	0.065 (4)	0.096 (7)	0.086 (5)	−0.005 (4)	0.023 (3)	0.018 (4)
C1'	0.056 (11)	0.063 (11)	0.054 (10)	−0.006 (8)	−0.002 (8)	0.010 (7)
C2'	0.063 (9)	0.050 (10)	0.036 (8)	−0.025 (7)	−0.002 (7)	0.001 (6)
C3'	0.071 (11)	0.094 (11)	0.065 (11)	0.019 (8)	0.017 (8)	0.028 (8)
C4'	0.0581 (18)	0.0524 (16)	0.0424 (17)	0.0046 (13)	0.0077 (14)	−0.0041 (13)
C5	0.0706 (19)	0.0489 (16)	0.0512 (17)	0.0003 (14)	0.0159 (15)	−0.0015 (13)
C6	0.0604 (16)	0.0541 (15)	0.0456 (15)	−0.0022 (13)	0.0114 (14)	0.0070 (14)
C7	0.0494 (15)	0.0435 (14)	0.0402 (14)	−0.0003 (11)	0.0014 (13)	−0.0018 (13)
C8	0.0573 (15)	0.0470 (16)	0.0443 (15)	0.0071 (13)	0.0043 (14)	0.0038 (14)
C9	0.114 (3)	0.090 (2)	0.063 (2)	0.024 (2)	0.040 (2)	0.0068 (19)
C10	0.0486 (15)	0.0442 (14)	0.0363 (14)	0.0024 (12)	0.0067 (13)	0.0012 (11)
C11	0.0599 (18)	0.0531 (16)	0.071 (2)	0.0039 (14)	−0.0038 (16)	0.0038 (15)
C12	0.066 (2)	0.077 (2)	0.086 (2)	0.0147 (17)	−0.0086 (17)	0.0120 (19)
C13	0.095 (3)	0.069 (2)	0.085 (2)	0.029 (2)	0.008 (2)	0.0193 (18)
C14	0.088 (2)	0.0448 (16)	0.072 (2)	0.0057 (17)	0.0225 (19)	0.0111 (15)
C15	0.0631 (17)	0.0475 (15)	0.0412 (15)	−0.0047 (13)	0.0167 (14)	−0.0008 (13)
C16	0.0644 (17)	0.0670 (18)	0.0516 (16)	0.0198 (15)	0.0014 (14)	−0.0017 (16)
C17	0.0508 (14)	0.0588 (16)	0.0410 (14)	0.0080 (13)	0.0049 (13)	0.0004 (12)
C18	0.074 (2)	0.082 (2)	0.0488 (18)	0.0280 (17)	0.0007 (15)	−0.0035 (15)
C19	0.081 (2)	0.094 (2)	0.067 (2)	0.018 (2)	0.0122 (19)	−0.019 (2)
C20	0.080 (2)	0.110 (3)	0.0417 (16)	0.009 (2)	0.0022 (16)	−0.0083 (18)
C21	0.0567 (17)	0.095 (2)	0.0466 (17)	0.0077 (18)	0.0010 (15)	−0.0069 (17)
C22	0.079 (2)	0.181 (4)	0.072 (2)	0.048 (3)	−0.018 (2)	0.004 (3)
C23	0.085 (2)	0.124 (3)	0.115 (3)	−0.023 (3)	0.015 (3)	−0.036 (3)
C24	0.0628 (19)	0.074 (2)	0.077 (2)	0.0079 (18)	0.0106 (19)	0.0023 (19)
C25	0.093 (3)	0.119 (3)	0.067 (2)	0.017 (2)	0.023 (2)	0.021 (2)
O7	0.187 (3)	0.0668 (16)	0.153 (3)	−0.0252 (18)	−0.005 (3)	0.0062 (18)
C26	0.156 (4)	0.107 (3)	0.095 (3)	0.026 (3)	0.020 (3)	0.021 (3)
C27	0.088 (2)	0.065 (2)	0.084 (3)	−0.0090 (19)	−0.024 (2)	0.005 (2)
C28	0.115 (3)	0.087 (2)	0.090 (3)	−0.009 (2)	−0.008 (2)	−0.007 (2)

Cl1—C15	1.741 (3)	C11—H11	0.9300
S2—O5	1.4418 (18)	C12—C13	1.370 (4)
S2—O3	1.4510 (18)	C12—H12	0.9300
S2—O4	1.4577 (18)	C13—C14	1.369 (5)
S2—C16	1.767 (3)	C13—H13	0.9300
O1—C8	1.188 (3)	C14—C15	1.385 (4)
O2—C8	1.319 (3)	C14—H14	0.9300
O2—C9	1.456 (4)	C16—C17	1.535 (4)
O6—C24	1.210 (4)	C16—H16A	0.9700
N1—C6	1.494 (3)	C16—H16B	0.9700
N1—C7	1.498 (3)	C17—C24	1.519 (4)
N1—H1A	0.88 (3)	C17—C21	1.543 (4)
N1—H1B	0.93 (3)	C17—C18	1.552 (4)
S1—C1	1.706 (5)	C18—C19	1.550 (4)
S1—C4	1.712 (3)	C18—H18A	0.9700
C1—C2	1.333 (6)	C18—H18B	0.9700
C1—H1	0.9300	C19—C20	1.537 (4)
C2—C3	1.472 (7)	C19—H19A	0.9700
C2—H2	0.9300	C19—H19B	0.9700
C3—C4	1.335 (7)	C20—C25	1.501 (5)
C3—H3	0.9300	C20—C21	1.546 (4)
C4—C5	1.504 (4)	C20—H20	0.9800
S1'—C1'	1.709 (10)	C21—C22	1.533 (4)
C1'—C2'	1.338 (9)	C21—C23	1.537 (5)
C1'—H1'	0.9300	C22—H22A	0.9600
C2'—C3'	1.499 (9)	C22—H22B	0.9600
C2'—H2'	0.9300	C22—H22C	0.9600
C3'—H3'	0.9300	C23—H23A	0.9600
C5—C6	1.517 (4)	C23—H23B	0.9600
C5—H5A	0.9700	C23—H23C	0.9600
C5—H5B	0.9700	C24—C25	1.515 (5)
C6—H6A	0.9700	C25—H25A	0.9700
C6—H6B	0.9700	C25—H25B	0.9700
C7—C8	1.514 (3)	O7—C27	1.205 (4)
C7—C10	1.521 (3)	C26—C27	1.474 (5)
C7—H7	0.9800	C26—H26A	0.9600
C9—H9A	0.9600	C26—H26B	0.9600
C9—H9B	0.9600	C26—H26C	0.9600
C9—H9C	0.9600	C27—C28	1.474 (5)
C10—C11	1.385 (3)	C28—H28A	0.9600
C10—C15	1.395 (3)	C28—H28B	0.9600
C11—C12	1.385 (4)	C28—H28C	0.9600
O5—S2—O3	113.33 (12)	C14—C15—C10	121.1 (3)
O5—S2—O4	111.76 (11)	C14—C15—Cl1	118.4 (2)
O3—S2—O4	112.61 (11)	C10—C15—Cl1	120.5 (2)
O5—S2—C16	107.82 (14)	C17—C16—S2	118.91 (18)
O3—S2—C16	106.12 (13)	C17—C16—H16A	107.6
O4—S2—C16	104.52 (12)	S2—C16—H16A	107.6
C8—O2—C9	117.2 (2)	C17—C16—H16B	107.6
C6—N1—C7	114.31 (19)	S2—C16—H16B	107.6
C6—N1—H1A	107.9 (16)	H16A—C16—H16B	107.0
C7—N1—H1A	108.2 (16)	C24—C17—C16	112.7 (2)
C6—N1—H1B	111.0 (18)	C24—C17—C21	100.4 (2)
C7—N1—H1B	107.8 (17)	C16—C17—C21	116.5 (2)
H1A—N1—H1B	107 (2)	C24—C17—C18	102.2 (2)
C1—S1—C4	92.6 (2)	C16—C17—C18	120.1 (2)
C2—C1—S1	111.6 (4)	C21—C17—C18	102.2 (2)
C2—C1—H1	124.2	C19—C18—C17	104.2 (2)
S1—C1—H1	124.2	C19—C18—H18A	110.9
C1—C2—C3	112.2 (4)	C17—C18—H18A	110.9
C1—C2—H2	123.9	C19—C18—H18B	110.9
C3—C2—H2	123.9	C17—C18—H18B	110.9
C4—C3—C2	111.9 (5)	H18A—C18—H18B	108.9
C4—C3—H3	124.1	C20—C19—C18	102.5 (2)
C2—C3—H3	124.1	C20—C19—H19A	111.3
C3—C4—C5	126.0 (4)	C18—C19—H19A	111.3
C3—C4—S1	111.5 (4)	C20—C19—H19B	111.3
C5—C4—S1	122.5 (2)	C18—C19—H19B	111.3
C2'—C1'—S1'	111.5 (9)	H19A—C19—H19B	109.2
C2'—C1'—H1'	124.2	C25—C20—C19	106.6 (3)
S1'—C1'—H1'	124.2	C25—C20—C21	102.8 (3)
C1'—C2'—C3'	110.9 (8)	C19—C20—C21	102.6 (3)
C1'—C2'—H2'	124.5	C25—C20—H20	114.5
C3'—C2'—H2'	124.5	C19—C20—H20	114.5
C2'—C3'—H3'	125.2	C21—C20—H20	114.5
C4—C5—C6	111.7 (2)	C22—C21—C23	108.6 (3)
C4—C5—H5A	109.3	C22—C21—C17	113.0 (3)
C6—C5—H5A	109.3	C23—C21—C17	112.7 (3)
C4—C5—H5B	109.3	C22—C21—C20	113.9 (3)
C6—C5—H5B	109.3	C23—C21—C20	113.9 (3)
H5A—C5—H5B	107.9	C17—C21—C20	94.3 (2)
N1—C6—C5	111.0 (2)	C21—C22—H22A	109.5
N1—C6—H6A	109.4	C21—C22—H22B	109.5
C5—C6—H6A	109.4	H22A—C22—H22B	109.5
N1—C6—H6B	109.4	C21—C22—H22C	109.5
C5—C6—H6B	109.4	H22A—C22—H22C	109.5
H6A—C6—H6B	108.0	H22B—C22—H22C	109.5
N1—C7—C8	107.46 (19)	C21—C23—H23A	109.5
N1—C7—C10	112.3 (2)	C21—C23—H23B	109.5
C8—C7—C10	113.4 (2)	H23A—C23—H23B	109.5
N1—C7—H7	107.8	C21—C23—H23C	109.5
C8—C7—H7	107.8	H23A—C23—H23C	109.5
C10—C7—H7	107.8	H23B—C23—H23C	109.5
O1—C8—O2	124.4 (3)	O6—C24—C25	127.1 (4)
O1—C8—C7	123.9 (2)	O6—C24—C17	126.5 (3)
O2—C8—C7	111.6 (2)	C25—C24—C17	106.4 (3)
O2—C9—H9A	109.5	C20—C25—C24	102.3 (3)
O2—C9—H9B	109.5	C20—C25—H25A	111.3
H9A—C9—H9B	109.5	C24—C25—H25A	111.3
O2—C9—H9C	109.5	C20—C25—H25B	111.3
H9A—C9—H9C	109.5	C24—C25—H25B	111.3
H9B—C9—H9C	109.5	H25A—C25—H25B	109.2
C11—C10—C15	117.9 (2)	C27—C26—H26A	109.5
C11—C10—C7	119.8 (2)	C27—C26—H26B	109.5
C15—C10—C7	122.3 (2)	H26A—C26—H26B	109.5
C10—C11—C12	120.9 (3)	C27—C26—H26C	109.5
C10—C11—H11	119.5	H26A—C26—H26C	109.5
C12—C11—H11	119.5	H26B—C26—H26C	109.5
C13—C12—C11	119.8 (3)	O7—C27—C26	122.7 (4)
C13—C12—H12	120.1	O7—C27—C28	121.0 (4)
C11—C12—H12	120.1	C26—C27—C28	116.2 (3)
C14—C13—C12	120.8 (3)	C27—C28—H28A	109.5
C14—C13—H13	119.6	C27—C28—H28B	109.5
C12—C13—H13	119.6	H28A—C28—H28B	109.5
C13—C14—C15	119.4 (3)	C27—C28—H28C	109.5
C13—C14—H14	120.3	H28A—C28—H28C	109.5
C15—C14—H14	120.3	H28B—C28—H28C	109.5
C4—S1—C1—C2	−3.8 (6)	O3—S2—C16—C17	−57.0 (2)
S1—C1—C2—C3	2.3 (10)	O4—S2—C16—C17	−176.2 (2)
C1—C2—C3—C4	1.0 (13)	S2—C16—C17—C24	116.6 (3)
C2—C3—C4—C5	177.8 (6)	S2—C16—C17—C21	−128.1 (2)
C2—C3—C4—S1	−3.8 (12)	S2—C16—C17—C18	−3.8 (4)
C1—S1—C4—C3	4.4 (8)	C24—C17—C18—C19	71.6 (3)
C1—S1—C4—C5	−177.1 (3)	C16—C17—C18—C19	−162.9 (3)
S1'—C1'—C2'—C3'	−11 (3)	C21—C17—C18—C19	−32.0 (3)
C3—C4—C5—C6	−101.8 (8)	C17—C18—C19—C20	−3.0 (3)
S1—C4—C5—C6	80.0 (3)	C18—C19—C20—C25	−70.6 (3)
C7—N1—C6—C5	−172.8 (2)	C18—C19—C20—C21	37.0 (3)
C4—C5—C6—N1	−176.6 (2)	C24—C17—C21—C22	66.0 (3)
C6—N1—C7—C8	−178.2 (2)	C16—C17—C21—C22	−55.9 (4)
C6—N1—C7—C10	−52.8 (3)	C18—C17—C21—C22	171.1 (3)
C9—O2—C8—O1	3.1 (4)	C24—C17—C21—C23	−170.4 (2)
C9—O2—C8—C7	−179.7 (2)	C16—C17—C21—C23	67.7 (3)
N1—C7—C8—O1	−6.6 (4)	C18—C17—C21—C23	−65.3 (3)
C10—C7—C8—O1	−131.3 (3)	C24—C17—C21—C20	−52.2 (3)
N1—C7—C8—O2	176.3 (2)	C16—C17—C21—C20	−174.2 (2)
C10—C7—C8—O2	51.6 (3)	C18—C17—C21—C20	52.8 (3)
N1—C7—C10—C11	−67.7 (3)	C25—C20—C21—C22	−62.5 (4)
C8—C7—C10—C11	54.3 (3)	C19—C20—C21—C22	−173.0 (3)
N1—C7—C10—C15	113.0 (3)	C25—C20—C21—C23	172.1 (3)
C8—C7—C10—C15	−124.9 (3)	C19—C20—C21—C23	61.6 (4)
C15—C10—C11—C12	−0.2 (4)	C25—C20—C21—C17	55.0 (3)
C7—C10—C11—C12	−179.5 (3)	C19—C20—C21—C17	−55.5 (3)
C10—C11—C12—C13	0.4 (5)	C16—C17—C24—O6	−20.7 (4)
C11—C12—C13—C14	0.0 (5)	C21—C17—C24—O6	−145.4 (3)
C12—C13—C14—C15	−0.5 (5)	C18—C17—C24—O6	109.5 (3)
C13—C14—C15—C10	0.7 (4)	C16—C17—C24—C25	157.9 (3)
C13—C14—C15—Cl1	−178.6 (2)	C21—C17—C24—C25	33.2 (3)
C11—C10—C15—C14	−0.4 (4)	C18—C17—C24—C25	−71.8 (3)
C7—C10—C15—C14	178.9 (2)	C19—C20—C25—C24	71.9 (3)
C11—C10—C15—Cl1	179.0 (2)	C21—C20—C25—C24	−35.6 (3)
C7—C10—C15—Cl1	−1.8 (3)	O6—C24—C25—C20	179.9 (3)
O5—S2—C16—C17	64.8 (2)	C17—C24—C25—C20	1.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O3	0.93 (3)	1.82 (3)	2.729 (3)	164 (3)
N1—H1A···O5i	0.88 (3)	2.63 (2)	3.180 (3)	121.1 (19)
N1—H1A···O4i	0.88 (3)	1.99 (3)	2.856 (3)	169 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O3	0.93 (3)	1.82 (3)	2.729 (3)	164 (3)
N1—H1A⋯O5i	0.88 (3)	2.63 (2)	3.180 (3)	121.1 (19)
N1—H1A⋯O4i	0.88 (3)	1.99 (3)	2.856 (3)	169 (2)

Symmetry code: (i) .