1-tert-Butyl 2-ethyl 5-bromo-3-(thio-phen-2-ylcarbon-yl)-1H-indole-1,2-dicarboxyl-ate.

In the title compound, C(21)H(20)BrNO(5)S, the thio-phene group is located above the mean plane of the indole ring and displays rotational disorder (i.e. rotation through 180°). The site occupancy of the major component is 0.902 (2), while that of the minor component is 0.098 (2). In the crystal, pairs of weak C-H⋯O inter-actions link the mol-ecules into centrosymmetric dimers.

Related literature

For background to the use of indoles as scaffolds in the synthesis of HIV-agents, see: Hassam et al. (2012 ▶) and for a recent review on stages of non-nucleoside reverse trans­criptase inhibitors, see: Reynolds et al. (2012 ▶). For the crystal structures of closely related compounds, see: Beddoes et al. (1986 ▶), Hassam & Smith (2012 ▶).

Experimental

Crystal data

C21H20BrNO5S

M = 478.35

Monoclinic,

a = 16.220 (3) Å

b = 15.361 (3) Å

c = 18.224 (4) Å

β = 113.792 (2)°

V = 4154.7 (15) Å3

Z = 8

Mo Kα radiation

μ = 2.11 mm−1

T = 100 K

0.34 × 0.21 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan [symmetry-related measurements (SADABS; Bruker, 2009 ▶)] T min = 0.537, T max = 0.721

23562 measured reflections

4855 independent reflections

4101 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.066

S = 1.05

4855 reflections

279 parameters

13 restraints

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶; Atwood & Barbour, 2003 ▶); software used to prepare material for publication: X-SEED.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813000809/jj2160sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000809/jj2160Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813000809/jj2160Isup3.cml

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

C21H20BrNO5S	F(000) = 1952
Mr = 478.35	Dx = 1.530 Mg m−3
Monoclinic, C2/c	Melting point: 370.13 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 16.220 (3) Å	Cell parameters from 6586 reflections
b = 15.361 (3) Å	θ = 2.4–27.6°
c = 18.224 (4) Å	µ = 2.11 mm−1
β = 113.792 (2)°	T = 100 K
V = 4154.7 (15) Å3	Rectangular prisms, colourless
Z = 8	0.34 × 0.21 × 0.17 mm

Bruker APEXII CCD diffractometer	4855 independent reflections
Radiation source: fine-focus sealed tube, Bruker SMART Apex	4101 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 28.2°, θmin = 1.9°
Absorption correction: multi-scan [symmetry-related measurements (SADABS; Bruker, 2009)]	h = −20→20
Tmin = 0.537, Tmax = 0.721	k = −19→19
23562 measured reflections	l = −24→24

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0296P)2 + 2.6317P] where P = (Fo2 + 2Fc2)/3
4855 reflections	(Δ/σ)max = 0.001
279 parameters	Δρmax = 0.38 e Å−3
13 restraints	Δρmin = −0.38 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	Occ. (<1)
Br1	−0.187401 (12)	−0.022969 (12)	−0.284234 (11)	0.02154 (6)
O1	0.21832 (9)	0.04217 (8)	0.06003 (8)	0.0220 (3)
N1	0.09114 (9)	0.12572 (9)	0.02039 (8)	0.0140 (3)
C1	0.04334 (12)	0.19832 (11)	0.02894 (10)	0.0143 (4)
O2	0.22623 (8)	0.18743 (8)	0.08505 (7)	0.0168 (3)
C2	0.03540 (10)	0.08118 (9)	−0.04949 (10)	0.0143 (3)
O3	0.11295 (9)	0.22588 (8)	0.16936 (7)	0.0223 (3)
C3	0.05264 (11)	0.00587 (10)	−0.08360 (9)	0.0165 (4)
H3	0.1083	−0.0243	−0.0598	0.020*
O4	0.06607 (8)	0.33759 (8)	0.08185 (7)	0.0167 (3)
C4	−0.01584 (11)	−0.02275 (11)	−0.15432 (10)	0.0173 (4)
H4	−0.0072	−0.0740	−0.1795	0.021*
O5	−0.14693 (9)	0.30149 (9)	−0.11372 (7)	0.0229 (3)
C5	−0.09682 (11)	0.02238 (10)	−0.18879 (10)	0.0167 (4)
C6	−0.11345 (11)	0.09814 (10)	−0.15555 (9)	0.0159 (4)
H6	−0.1687	0.1289	−0.1802	0.019*
C7	−0.04550 (10)	0.12713 (11)	−0.08437 (9)	0.0143 (3)
C8	−0.03952 (12)	0.20088 (11)	−0.03284 (10)	0.0147 (4)
C9	−0.11022 (12)	0.26847 (12)	−0.04742 (11)	0.0165 (4)
C10	−0.13346 (11)	0.29232 (11)	0.01992 (10)	0.0147 (4)
C14	0.07984 (11)	0.25376 (11)	0.10226 (11)	0.0158 (4)
C15	0.08485 (13)	0.39806 (12)	0.14842 (11)	0.0217 (4)
H15A	0.1485	0.3932	0.1869	0.026*
H15B	0.0457	0.3853	0.1771	0.026*
C16	0.06589 (15)	0.48791 (13)	0.11250 (13)	0.0294 (5)
H16C	0.0026	0.4918	0.0748	0.044*
H16A	0.1047	0.4994	0.0840	0.044*
H16B	0.0780	0.5310	0.1553	0.044*
C17	0.18541 (12)	0.11267 (11)	0.05822 (10)	0.0159 (4)
C18	0.32643 (12)	0.19106 (12)	0.13180 (11)	0.0190 (4)
C19	0.37308 (13)	0.16063 (14)	0.07930 (12)	0.0249 (4)
H19C	0.3471	0.1907	0.0275	0.037*
H19A	0.3648	0.0977	0.0708	0.037*
H19B	0.4376	0.1738	0.1056	0.037*
C20	0.34088 (14)	0.28765 (13)	0.14976 (13)	0.0293 (5)
H20A	0.3061	0.3063	0.1802	0.044*
H20B	0.3209	0.3202	0.0993	0.044*
H20C	0.4050	0.2988	0.1814	0.044*
C21	0.35137 (14)	0.13828 (14)	0.20765 (11)	0.0278 (5)
H21A	0.3417	0.0763	0.1940	0.042*
H21C	0.3137	0.1561	0.2357	0.042*
H21B	0.4149	0.1481	0.2425	0.042*
S1A	−0.18632 (4)	0.39061 (3)	0.01797 (3)	0.01650 (16)	0.9021 (19)
C11A	−0.12031 (18)	0.24830 (18)	0.08752 (18)	0.0212 (5)	0.902 (2)
H11A	−0.0924	0.1927	0.0987	0.025*	0.9021 (19)
C12A	−0.1506 (2)	0.2902 (3)	0.1402 (3)	0.0196 (4)	0.9021 (19)
H12A	−0.1462	0.2667	0.1899	0.024*	0.9021 (19)
C13A	−0.1874 (3)	0.3695 (3)	0.11084 (15)	0.0161 (6)	0.9021 (19)
H13A	−0.2108	0.4084	0.1382	0.019*	0.9021 (19)
S1B	−0.1088 (5)	0.2256 (4)	0.1026 (3)	0.01650 (16)	0.0979 (19)
C11B	−0.1782 (13)	0.3643 (9)	0.0245 (15)	0.0212 (5)	0.0979 (19)
H11B	−0.1971	0.4082	−0.0157	0.025*	0.0979 (19)
C12B	−0.194 (3)	0.368 (3)	0.0944 (18)	0.0161 (6)	0.0979 (19)
H12B	−0.2251	0.4149	0.1065	0.019*	0.0979 (19)
C13B	−0.161 (2)	0.298 (2)	0.143 (3)	0.0196 (4)	0.0979 (19)
H13B	−0.1655	0.2895	0.1930	0.024*	0.0979 (19)

	U11	U22	U33	U12	U13	U23
Br1	0.01920 (10)	0.02324 (11)	0.01899 (10)	−0.00231 (8)	0.00438 (7)	−0.00483 (7)
O1	0.0186 (7)	0.0174 (7)	0.0266 (7)	0.0045 (5)	0.0056 (6)	−0.0011 (5)
N1	0.0133 (7)	0.0144 (7)	0.0138 (7)	0.0008 (6)	0.0051 (6)	−0.0017 (6)
C1	0.0166 (9)	0.0130 (8)	0.0164 (9)	0.0025 (7)	0.0099 (7)	0.0014 (7)
O2	0.0136 (6)	0.0167 (6)	0.0178 (6)	−0.0006 (5)	0.0040 (5)	−0.0017 (5)
C2	0.0147 (8)	0.0139 (8)	0.0145 (8)	−0.0028 (7)	0.0061 (7)	0.0000 (7)
O3	0.0296 (7)	0.0216 (7)	0.0148 (7)	0.0044 (6)	0.0078 (6)	0.0005 (5)
C3	0.0165 (9)	0.0145 (9)	0.0199 (9)	0.0022 (7)	0.0087 (7)	0.0006 (7)
O4	0.0196 (6)	0.0139 (6)	0.0158 (6)	−0.0004 (5)	0.0062 (5)	−0.0028 (5)
C4	0.0213 (9)	0.0141 (8)	0.0189 (9)	−0.0002 (7)	0.0106 (8)	−0.0022 (7)
O5	0.0266 (7)	0.0251 (7)	0.0167 (7)	0.0076 (6)	0.0084 (6)	0.0043 (5)
C5	0.0176 (9)	0.0186 (9)	0.0138 (8)	−0.0040 (7)	0.0065 (7)	−0.0013 (7)
C6	0.0152 (9)	0.0179 (9)	0.0158 (9)	0.0003 (7)	0.0075 (7)	0.0019 (7)
C7	0.0158 (9)	0.0143 (8)	0.0158 (9)	0.0009 (7)	0.0093 (7)	0.0016 (7)
C8	0.0185 (9)	0.0143 (8)	0.0146 (9)	0.0008 (7)	0.0103 (7)	0.0010 (7)
C9	0.0154 (9)	0.0165 (9)	0.0183 (9)	−0.0005 (7)	0.0074 (7)	−0.0011 (7)
C10	0.0116 (8)	0.0154 (8)	0.0172 (9)	0.0019 (7)	0.0059 (7)	−0.0003 (7)
C14	0.0131 (8)	0.0175 (9)	0.0193 (9)	0.0013 (7)	0.0091 (7)	−0.0015 (7)
C15	0.0258 (10)	0.0202 (10)	0.0167 (9)	−0.0030 (8)	0.0060 (8)	−0.0082 (7)
C16	0.0334 (12)	0.0202 (10)	0.0264 (11)	0.0014 (9)	0.0034 (9)	−0.0064 (8)
C17	0.0172 (9)	0.0186 (9)	0.0124 (8)	0.0006 (7)	0.0068 (7)	0.0005 (7)
C18	0.0128 (8)	0.0260 (10)	0.0161 (9)	−0.0030 (7)	0.0036 (7)	−0.0009 (7)
C19	0.0187 (10)	0.0322 (11)	0.0250 (10)	0.0017 (8)	0.0100 (8)	0.0047 (9)
C20	0.0249 (11)	0.0277 (11)	0.0309 (11)	−0.0083 (9)	0.0068 (9)	−0.0066 (9)
C21	0.0235 (10)	0.0381 (12)	0.0178 (10)	−0.0044 (9)	0.0043 (8)	0.0046 (9)
S1A	0.0180 (3)	0.0143 (3)	0.0192 (3)	0.0051 (2)	0.0095 (2)	0.0010 (2)
C11A	0.0184 (13)	0.0143 (13)	0.0291 (14)	0.0058 (10)	0.0080 (11)	0.0014 (10)
C12A	0.0206 (13)	0.0209 (13)	0.0189 (10)	0.0016 (10)	0.0096 (10)	0.0000 (8)
C13A	0.0188 (12)	0.0188 (9)	0.0142 (15)	0.0031 (9)	0.0102 (14)	−0.0018 (14)
S1B	0.0180 (3)	0.0143 (3)	0.0192 (3)	0.0051 (2)	0.0095 (2)	0.0010 (2)
C11B	0.0184 (13)	0.0143 (13)	0.0291 (14)	0.0058 (10)	0.0080 (11)	0.0014 (10)
C12B	0.0188 (12)	0.0188 (9)	0.0142 (15)	0.0031 (9)	0.0102 (14)	−0.0018 (14)
C13B	0.0206 (13)	0.0209 (13)	0.0189 (10)	0.0016 (10)	0.0096 (10)	0.0000 (8)

Br1—C5	1.8993 (17)	C15—H15A	0.9900
O1—C17	1.202 (2)	C15—H15B	0.9900
N1—C1	1.402 (2)	C16—H16C	0.9800
N1—C2	1.406 (2)	C16—H16A	0.9800
N1—C17	1.415 (2)	C16—H16B	0.9800
C1—C8	1.362 (2)	C18—C21	1.510 (3)
C1—C14	1.491 (2)	C18—C19	1.514 (3)
O2—C17	1.317 (2)	C18—C20	1.517 (3)
O2—C18	1.501 (2)	C19—H19C	0.9800
C2—C3	1.3940 (15)	C19—H19A	0.9800
C2—C7	1.3968 (15)	C19—H19B	0.9800
O3—C14	1.199 (2)	C20—H20A	0.9800
C3—C4	1.3903 (16)	C20—H20B	0.9800
C3—H3	0.9500	C20—H20C	0.9800
O4—C14	1.334 (2)	C21—H21A	0.9800
O4—C15	1.459 (2)	C21—H21C	0.9800
C4—C5	1.3909 (16)	C21—H21B	0.9800
C4—H4	0.9500	S1A—C13A	1.730 (3)
O5—C9	1.221 (2)	C11A—C12A	1.400 (3)
C5—C6	1.3878 (15)	C11A—H11A	0.9500
C6—C7	1.3935 (16)	C12A—C13A	1.367 (3)
C6—H6	0.9500	C12A—H12A	0.9500
C7—C8	1.450 (2)	C13A—H13A	0.9500
C8—C9	1.489 (2)	S1B—C13B	1.730 (3)
C9—C10	1.468 (2)	C11B—C12B	1.400 (4)
C10—C11B	1.344 (4)	C11B—H11B	0.9500
C10—C11A	1.345 (3)	C12B—C13B	1.367 (3)
C10—S1A	1.7297 (17)	C12B—H12B	0.9500
C10—S1B	1.730 (2)	C13B—H13B	0.9500
C15—C16	1.505 (3)
C1—N1—C2	107.77 (13)	H16C—C16—H16A	109.5
C1—N1—C17	126.56 (15)	C15—C16—H16B	109.5
C2—N1—C17	123.07 (13)	H16C—C16—H16B	109.5
C8—C1—N1	109.67 (15)	H16A—C16—H16B	109.5
C8—C1—C14	128.83 (16)	O1—C17—O2	128.62 (17)
N1—C1—C14	121.09 (15)	O1—C17—N1	121.44 (16)
C17—O2—C18	120.67 (14)	O2—C17—N1	109.86 (15)
C3—C2—C7	122.48 (14)	O2—C18—C21	109.18 (15)
C3—C2—N1	129.51 (13)	O2—C18—C19	109.43 (14)
C7—C2—N1	108.00 (12)	C21—C18—C19	113.28 (17)
C4—C3—C2	116.55 (15)	O2—C18—C20	101.33 (14)
C4—C3—H3	121.7	C21—C18—C20	111.51 (16)
C2—C3—H3	121.7	C19—C18—C20	111.42 (16)
C14—O4—C15	115.31 (14)	C18—C19—H19C	109.5
C3—C4—C5	121.11 (15)	C18—C19—H19A	109.5
C3—C4—H4	119.4	H19C—C19—H19A	109.5
C5—C4—H4	119.4	C18—C19—H19B	109.5
C6—C5—C4	122.36 (15)	H19C—C19—H19B	109.5
C6—C5—Br1	119.51 (11)	H19A—C19—H19B	109.5
C4—C5—Br1	118.13 (11)	C18—C20—H20A	109.5
C5—C6—C7	117.02 (15)	C18—C20—H20B	109.5
C5—C6—H6	121.5	H20A—C20—H20B	109.5
C7—C6—H6	121.5	C18—C20—H20C	109.5
C6—C7—C2	120.47 (14)	H20A—C20—H20C	109.5
C6—C7—C8	132.37 (15)	H20B—C20—H20C	109.5
C2—C7—C8	107.16 (14)	C18—C21—H21A	109.5
C1—C8—C7	107.38 (15)	C18—C21—H21C	109.5
C1—C8—C9	126.85 (16)	H21A—C21—H21C	109.5
C7—C8—C9	125.72 (15)	C18—C21—H21B	109.5
O5—C9—C10	122.43 (16)	H21A—C21—H21B	109.5
O5—C9—C8	119.94 (16)	H21C—C21—H21B	109.5
C10—C9—C8	117.62 (15)	C10—S1A—C13A	90.96 (18)
C11B—C10—C11A	104.3 (12)	C10—C11A—C12A	115.3 (3)
C11B—C10—C9	125.8 (12)	C10—C11A—H11A	122.3
C11A—C10—C9	129.86 (16)	C12A—C11A—H11A	122.3
C11A—C10—S1A	110.60 (15)	C13A—C12A—C11A	111.1 (4)
C9—C10—S1A	119.53 (12)	C13A—C12A—H12A	124.5
C11B—C10—S1B	112.0 (12)	C11A—C12A—H12A	124.5
C9—C10—S1B	122.2 (3)	C12A—C13A—S1A	112.1 (4)
S1A—C10—S1B	118.3 (3)	C12A—C13A—H13A	124.0
O3—C14—O4	125.80 (16)	S1A—C13A—H13A	124.0
O3—C14—C1	124.23 (16)	C13B—S1B—C10	90.7 (19)
O4—C14—C1	109.90 (15)	C10—C11B—C12B	113 (3)
O4—C15—C16	106.54 (15)	C10—C11B—H11B	123.4
O4—C15—H15A	110.4	C12B—C11B—H11B	123.4
C16—C15—H15A	110.4	C13B—C12B—C11B	113 (4)
O4—C15—H15B	110.4	C13B—C12B—H12B	123.6
C16—C15—H15B	110.4	C11B—C12B—H12B	123.6
H15A—C15—H15B	108.6	C12B—C13B—S1B	111 (4)
C15—C16—H16C	109.5	C12B—C13B—H13B	124.4
C15—C16—H16A	109.5	S1B—C13B—H13B	124.4
C2—N1—C1—C8	−0.25 (19)	C8—C9—C10—S1B	−19.6 (4)
C17—N1—C1—C8	161.74 (16)	C15—O4—C14—O3	−6.9 (2)
C2—N1—C1—C14	173.05 (15)	C15—O4—C14—C1	170.13 (14)
C17—N1—C1—C14	−25.0 (3)	C8—C1—C14—O3	127.0 (2)
C1—N1—C2—C3	179.52 (17)	N1—C1—C14—O3	−44.9 (3)
C17—N1—C2—C3	16.8 (3)	C8—C1—C14—O4	−50.1 (2)
C1—N1—C2—C7	1.06 (19)	N1—C1—C14—O4	138.06 (16)
C17—N1—C2—C7	−161.70 (15)	C14—O4—C15—C16	179.51 (15)
C7—C2—C3—C4	−1.0 (3)	C18—O2—C17—O1	−6.5 (3)
N1—C2—C3—C4	−179.25 (17)	C18—O2—C17—N1	176.60 (14)
C2—C3—C4—C5	0.3 (3)	C1—N1—C17—O1	165.06 (17)
C3—C4—C5—C6	0.7 (3)	C2—N1—C17—O1	−35.5 (3)
C3—C4—C5—Br1	−178.72 (14)	C1—N1—C17—O2	−17.8 (2)
C4—C5—C6—C7	−1.1 (3)	C2—N1—C17—O2	141.64 (15)
Br1—C5—C6—C7	178.34 (12)	C17—O2—C18—C21	−61.6 (2)
C5—C6—C7—C2	0.4 (2)	C17—O2—C18—C19	62.9 (2)
C5—C6—C7—C8	−178.75 (17)	C17—O2—C18—C20	−179.30 (15)
C3—C2—C7—C6	0.6 (3)	C11B—C10—S1A—C13A	24 (8)
N1—C2—C7—C6	179.21 (15)	C11A—C10—S1A—C13A	0.89 (19)
C3—C2—C7—C8	179.98 (16)	C9—C10—S1A—C13A	−179.27 (18)
N1—C2—C7—C8	−1.43 (19)	S1B—C10—S1A—C13A	0.2 (3)
N1—C1—C8—C7	−0.63 (19)	C11B—C10—C11A—C12A	−3.2 (11)
C14—C1—C8—C7	−173.26 (16)	C9—C10—C11A—C12A	179.8 (2)
N1—C1—C8—C9	−178.36 (16)	S1A—C10—C11A—C12A	−0.4 (3)
C14—C1—C8—C9	9.0 (3)	S1B—C10—C11A—C12A	175 (3)
C6—C7—C8—C1	−179.46 (18)	C10—C11A—C12A—C13A	−0.5 (3)
C2—C7—C8—C1	1.28 (19)	C11A—C12A—C13A—S1A	1.2 (2)
C6—C7—C8—C9	−1.7 (3)	C10—S1A—C13A—C12A	−1.20 (17)
C2—C7—C8—C9	179.04 (16)	C11B—C10—S1B—C13B	0.0 (4)
C1—C8—C9—O5	131.0 (2)	C11A—C10—S1B—C13B	−2 (3)
C7—C8—C9—O5	−46.3 (3)	C9—C10—S1B—C13B	−177.5 (11)
C1—C8—C9—C10	−49.4 (3)	S1A—C10—S1B—C13B	3.1 (10)
C7—C8—C9—C10	133.27 (18)	C11A—C10—C11B—C12B	0.3 (6)
O5—C9—C10—C11B	−17.3 (12)	C9—C10—C11B—C12B	177.4 (11)
C8—C9—C10—C11B	163.2 (11)	S1A—C10—C11B—C12B	−157 (8)
O5—C9—C10—C11A	159.1 (2)	S1B—C10—C11B—C12B	0.0 (5)
C8—C9—C10—C11A	−20.4 (3)	C10—C11B—C12B—C13B	0.0 (3)
O5—C9—C10—S1A	−20.7 (2)	C11B—C12B—C13B—S1B	0.0 (2)
C8—C9—C10—S1A	159.78 (13)	C10—S1B—C13B—C12B	0.0 (3)
O5—C9—C10—S1B	159.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C12A—H12A···O3i	0.95	2.48	3.418 (5)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12A—H12A⋯O3i	0.95	2.48	3.418 (5)	169

Symmetry code: (i) .