3-(Benzothia-zol-2-yl)-3-(prop-2-yn-yl)hex-5-yn-2-one.

The title compound, C(16)H(13)NOS, was prepared by alkyl-ation of 1-(benzothia-zol-2-yl)propan-2-one with propargyl bromide. The asymmetric unit contains two mol-ecules that are crystallographically independent but linked to each other by non-classical C-H⋯O hydrogen bonds, building up a dimeric substructure. The benzothia-zole rings are essentially planar with maximum deviations of 0.005 (1) and 0.007 (2) Å for the N atoms. Although the two mol-ecules have similar bond distances and angles, they slightly differ in the orientation of the benzothia-zole ring with respect to the two propargyl groups and the acetonyl unit . In the crystal, inter-molecular C-H⋯O inter-actions link the dimeric subunits into a two-dimensional array in the bc plane.

Related literature

For background to the applications of benzothia­zoles in the chemical industry, see: Bradshaw et al. (2002 ▶); Delmas et al. (2002 ▶); Hutchinson et al. (2002 ▶). For the pharmacological activity of benzothia­zole derivatives, see: Repiĉ et al. (2001 ▶); Schwartz et al. (1992 ▶).

Experimental

Crystal data

C16H13NOS

M = 267.34

Monoclinic,

a = 7.7913 (1) Å

b = 30.2051 (6) Å

c = 12.4437 (2) Å

β = 106.161 (1)°

V = 2812.74 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.22 mm−1

T = 298 K

0.36 × 0.30 × 0.20 mm

Data collection

Bruker X8 APEXII CCD area-detector diffractometer

45783 measured reflections

8407 independent reflections

5449 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.128

S = 1.01

8407 reflections

391 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810009293/im2184sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009293/im2184Isup2.hkl

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

C16H13NOS	Z = 8
Mr = 267.34	F(000) = 1120
Monoclinic, P21/n	Dx = 1.263 Mg m−3
Hall symbol: -p 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.7913 (1) Å	θ = 7.0–30.3°
b = 30.2051 (6) Å	µ = 0.22 mm−1
c = 12.4437 (2) Å	T = 298 K
β = 106.161 (1)°	Parallelepiped, clear pale yellow
V = 2812.74 (8) Å3	0.36 × 0.30 × 0.20 mm

Bruker X8 APEX CCD area-detector diffractometer	5449 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.052
graphite	θmax = 30.3°, θmin = 2.2°
φ and ω scans	h = −11→11
45783 measured reflections	k = −42→42
8407 independent reflections	l = −17→17

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0611P)2 + 0.4268P] where P = (Fo2 + 2Fc2)/3
8407 reflections	(Δ/σ)max = 0.001
391 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.19 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
O1	0.62822 (19)	0.02125 (4)	0.85422 (13)	0.0661 (4)
S1	0.45815 (6)	0.126638 (14)	0.65398 (3)	0.04635 (12)
N1	0.55435 (17)	0.17249 (4)	0.83678 (10)	0.0379 (3)
C1	0.4413 (2)	0.19924 (5)	0.75663 (12)	0.0360 (3)
C2	0.3957 (2)	0.24295 (6)	0.77253 (15)	0.0463 (4)
H2	0.440 (2)	0.2551 (6)	0.8419 (16)	0.045 (5)*
C3	0.2901 (2)	0.26604 (6)	0.68364 (16)	0.0514 (4)
H3	0.260 (3)	0.2954 (7)	0.6956 (16)	0.059 (6)*
C4	0.2271 (3)	0.24671 (7)	0.57885 (16)	0.0541 (5)
H4	0.154 (3)	0.2633 (7)	0.5185 (17)	0.063 (6)*
C5	0.2673 (2)	0.20358 (7)	0.56119 (15)	0.0496 (4)
H5	0.222 (3)	0.1904 (7)	0.4940 (17)	0.062 (6)*
C6	0.3754 (2)	0.17996 (5)	0.65053 (13)	0.0383 (3)
C7	0.5758 (2)	0.13457 (5)	0.79517 (12)	0.0357 (3)
C8	0.6974 (2)	0.09826 (5)	0.85737 (12)	0.0372 (3)
C9	0.5878 (2)	0.05786 (5)	0.87635 (13)	0.0435 (4)
C10	0.4340 (3)	0.06577 (7)	0.92442 (17)	0.0601 (5)
H10A	0.4657	0.0883	0.9808	0.090*
H10B	0.4062	0.0389	0.9571	0.090*
H10C	0.3317	0.0752	0.8661	0.090*
C11	0.8066 (2)	0.11589 (6)	0.97374 (13)	0.0442 (4)
H11A	0.8691	0.1427	0.9639	0.053*
H11B	0.7256	0.1232	1.0178	0.053*
C12	0.9358 (3)	0.08305 (6)	1.03360 (14)	0.0516 (4)
C13	1.0392 (4)	0.05574 (9)	1.07695 (19)	0.0747 (7)
H13	1.122 (4)	0.0344 (9)	1.112 (2)	0.099 (9)*
C14	0.8253 (2)	0.08345 (6)	0.78856 (14)	0.0453 (4)
H14A	0.9067	0.0612	0.8303	0.054*
H14B	0.7560	0.0701	0.7191	0.054*
C15	0.9280 (3)	0.12022 (7)	0.76328 (16)	0.0543 (5)
C16	1.0073 (3)	0.15030 (10)	0.7428 (2)	0.0793 (7)
H16	1.067 (4)	0.1724 (8)	0.724 (2)	0.088 (8)*
O2	0.6762 (2)	0.05561 (5)	0.52220 (10)	0.0639 (4)
S2	0.55463 (6)	0.170295 (14)	0.37374 (3)	0.04545 (12)
N2	0.49980 (18)	0.12720 (4)	0.18749 (10)	0.0388 (3)
C17	0.4081 (2)	0.16709 (5)	0.16241 (13)	0.0391 (3)
C18	0.3085 (3)	0.18000 (7)	0.05589 (16)	0.0563 (5)
H18	0.299 (3)	0.1604 (7)	−0.0094 (19)	0.074 (7)*
C19	0.2278 (3)	0.22127 (8)	0.04356 (19)	0.0658 (6)
H19	0.162 (3)	0.2295 (7)	−0.0307 (18)	0.072 (6)*
C20	0.2450 (3)	0.24907 (7)	0.1344 (2)	0.0621 (5)
H20	0.183 (3)	0.2782 (7)	0.1227 (18)	0.072 (6)*
C21	0.3403 (3)	0.23676 (6)	0.24036 (18)	0.0540 (5)
H21	0.353 (3)	0.2552 (7)	0.3008 (17)	0.068 (6)*
C22	0.4227 (2)	0.19521 (5)	0.25372 (13)	0.0395 (3)
C23	0.5807 (2)	0.12458 (5)	0.29265 (12)	0.0338 (3)
C24	0.6913 (2)	0.08534 (5)	0.34795 (12)	0.0356 (3)
C25	0.5961 (2)	0.06227 (5)	0.42620 (13)	0.0434 (4)
C26	0.4072 (3)	0.04820 (7)	0.37852 (18)	0.0634 (5)
H26A	0.3602	0.0613	0.3059	0.095*
H26B	0.3376	0.0577	0.4269	0.095*
H26C	0.4018	0.0165	0.3719	0.095*
C27	0.7065 (2)	0.05229 (5)	0.25588 (12)	0.0395 (3)
H27A	0.5876	0.0431	0.2137	0.047*
H27B	0.7615	0.0671	0.2047	0.047*
C28	0.8117 (3)	0.01322 (7)	0.30197 (15)	0.0583 (5)
C29	0.8994 (5)	−0.01727 (10)	0.3395 (2)	0.1035 (11)
H29	0.970 (4)	−0.0425 (11)	0.363 (3)	0.128 (11)*
C30	0.8784 (2)	0.10077 (6)	0.41712 (14)	0.0499 (4)
H30A	0.8661	0.1203	0.4765	0.060*
H30B	0.9477	0.0752	0.4515	0.060*
C31	0.9732 (2)	0.12394 (6)	0.34835 (17)	0.0527 (4)
C32	1.0447 (3)	0.14150 (8)	0.2886 (2)	0.0713 (6)
H32	1.099 (4)	0.1568 (10)	0.237 (3)	0.123 (11)*

	U11	U22	U33	U12	U13	U23
O1	0.0675 (9)	0.0358 (7)	0.0939 (11)	−0.0001 (6)	0.0208 (8)	−0.0075 (7)
S1	0.0574 (3)	0.0398 (2)	0.0367 (2)	0.00420 (18)	0.00457 (18)	−0.00849 (16)
N1	0.0421 (7)	0.0375 (7)	0.0339 (6)	0.0034 (5)	0.0102 (5)	−0.0030 (5)
C1	0.0343 (8)	0.0377 (8)	0.0362 (7)	0.0020 (6)	0.0103 (6)	−0.0021 (6)
C2	0.0481 (10)	0.0430 (9)	0.0454 (9)	0.0083 (7)	0.0092 (8)	−0.0074 (7)
C3	0.0486 (10)	0.0437 (10)	0.0583 (11)	0.0160 (8)	0.0089 (8)	−0.0015 (8)
C4	0.0479 (10)	0.0568 (12)	0.0509 (10)	0.0143 (9)	0.0029 (8)	0.0066 (8)
C5	0.0469 (10)	0.0575 (11)	0.0387 (9)	0.0050 (8)	0.0022 (8)	−0.0022 (8)
C6	0.0355 (8)	0.0411 (8)	0.0380 (7)	−0.0008 (6)	0.0095 (6)	−0.0030 (6)
C7	0.0399 (8)	0.0350 (8)	0.0320 (7)	−0.0012 (6)	0.0097 (6)	−0.0025 (6)
C8	0.0434 (8)	0.0330 (8)	0.0349 (7)	0.0029 (6)	0.0102 (6)	−0.0030 (6)
C9	0.0509 (10)	0.0360 (9)	0.0395 (8)	−0.0005 (7)	0.0059 (7)	0.0001 (6)
C10	0.0698 (13)	0.0564 (12)	0.0613 (11)	−0.0093 (10)	0.0302 (10)	0.0011 (9)
C11	0.0499 (10)	0.0423 (9)	0.0370 (8)	0.0031 (7)	0.0065 (7)	−0.0044 (6)
C12	0.0552 (11)	0.0539 (11)	0.0412 (9)	0.0043 (9)	0.0060 (8)	−0.0048 (8)
C13	0.0797 (16)	0.0767 (16)	0.0555 (12)	0.0263 (13)	−0.0016 (11)	0.0013 (11)
C14	0.0508 (10)	0.0452 (9)	0.0405 (8)	0.0097 (7)	0.0139 (7)	−0.0015 (7)
C15	0.0501 (10)	0.0620 (12)	0.0560 (10)	0.0085 (9)	0.0234 (9)	0.0035 (9)
C16	0.0670 (15)	0.0808 (18)	0.1034 (19)	−0.0018 (13)	0.0460 (15)	0.0091 (14)
O2	0.0870 (10)	0.0675 (9)	0.0372 (6)	0.0073 (8)	0.0172 (7)	0.0111 (6)
S2	0.0591 (3)	0.0369 (2)	0.0393 (2)	0.00400 (18)	0.01197 (19)	−0.00679 (16)
N2	0.0446 (7)	0.0345 (7)	0.0348 (6)	0.0052 (6)	0.0072 (6)	0.0006 (5)
C17	0.0383 (8)	0.0361 (8)	0.0431 (8)	0.0041 (6)	0.0117 (7)	0.0047 (6)
C18	0.0616 (12)	0.0554 (11)	0.0476 (10)	0.0185 (9)	0.0080 (9)	0.0062 (8)
C19	0.0651 (13)	0.0678 (14)	0.0622 (12)	0.0292 (11)	0.0138 (11)	0.0211 (11)
C20	0.0615 (12)	0.0481 (11)	0.0815 (15)	0.0242 (10)	0.0280 (11)	0.0162 (10)
C21	0.0571 (11)	0.0391 (10)	0.0713 (13)	0.0095 (8)	0.0272 (10)	0.0009 (9)
C22	0.0392 (8)	0.0334 (8)	0.0488 (9)	0.0008 (6)	0.0170 (7)	0.0020 (6)
C23	0.0384 (8)	0.0288 (7)	0.0345 (7)	−0.0020 (6)	0.0107 (6)	−0.0022 (6)
C24	0.0416 (8)	0.0313 (7)	0.0311 (7)	0.0030 (6)	0.0056 (6)	0.0003 (5)
C25	0.0624 (11)	0.0311 (8)	0.0387 (8)	0.0070 (7)	0.0171 (8)	0.0026 (6)
C26	0.0670 (13)	0.0606 (13)	0.0681 (13)	−0.0082 (10)	0.0277 (11)	0.0132 (10)
C27	0.0472 (9)	0.0354 (8)	0.0338 (7)	0.0058 (7)	0.0080 (7)	−0.0016 (6)
C28	0.0786 (14)	0.0538 (11)	0.0425 (9)	0.0245 (10)	0.0166 (9)	0.0008 (8)
C29	0.158 (3)	0.093 (2)	0.0589 (14)	0.080 (2)	0.0293 (16)	0.0151 (13)
C30	0.0471 (10)	0.0504 (10)	0.0426 (9)	0.0029 (8)	−0.0030 (7)	−0.0021 (7)
C31	0.0404 (9)	0.0481 (10)	0.0633 (11)	−0.0031 (8)	0.0041 (8)	−0.0116 (9)
C32	0.0557 (13)	0.0712 (15)	0.0896 (17)	−0.0181 (11)	0.0245 (12)	−0.0116 (13)

O1—C9	1.203 (2)	O2—C25	1.201 (2)
S1—C6	1.7308 (17)	S2—C22	1.7319 (17)
S1—C7	1.7573 (16)	S2—C23	1.7549 (15)
N1—C7	1.2869 (19)	N2—C23	1.2873 (19)
N1—C1	1.3909 (19)	N2—C17	1.3912 (19)
C1—C2	1.396 (2)	C17—C18	1.393 (2)
C1—C6	1.403 (2)	C17—C22	1.398 (2)
C2—C3	1.371 (2)	C18—C19	1.385 (3)
C2—H2	0.912 (18)	C18—H18	0.99 (2)
C3—C4	1.388 (3)	C19—C20	1.384 (3)
C3—H3	0.94 (2)	C19—H19	0.96 (2)
C4—C5	1.372 (3)	C20—C21	1.372 (3)
C4—H4	0.95 (2)	C20—H20	1.00 (2)
C5—C6	1.390 (2)	C21—C22	1.398 (2)
C5—H5	0.91 (2)	C21—H21	0.92 (2)
C7—C8	1.514 (2)	C23—C24	1.514 (2)
C8—C9	1.545 (2)	C24—C30	1.544 (2)
C8—C14	1.549 (2)	C24—C25	1.544 (2)
C8—C11	1.555 (2)	C24—C27	1.549 (2)
C9—C10	1.500 (3)	C25—C26	1.488 (3)
C10—H10A	0.9600	C26—H26A	0.9600
C10—H10B	0.9600	C26—H26B	0.9600
C10—H10C	0.9600	C26—H26C	0.9600
C11—C12	1.461 (2)	C27—C28	1.460 (2)
C11—H11A	0.9700	C27—H27A	0.9700
C11—H11B	0.9700	C27—H27B	0.9700
C12—C13	1.174 (3)	C28—C29	1.164 (3)
C13—H13	0.93 (3)	C29—H29	0.94 (3)
C14—C15	1.454 (3)	C30—C31	1.456 (3)
C14—H14A	0.9700	C30—H30A	0.9700
C14—H14B	0.9700	C30—H30B	0.9700
C15—C16	1.166 (3)	C31—C32	1.173 (3)
C16—H16	0.88 (3)	C32—H32	0.98 (3)
C6—S1—C7	89.14 (7)	C22—S2—C23	88.96 (7)
C7—N1—C1	110.83 (13)	C23—N2—C17	110.90 (13)
N1—C1—C2	125.68 (14)	N2—C17—C18	124.86 (15)
N1—C1—C6	115.25 (14)	N2—C17—C22	115.06 (14)
C2—C1—C6	119.03 (15)	C18—C17—C22	120.08 (15)
C3—C2—C1	119.07 (16)	C19—C18—C17	118.23 (19)
C3—C2—H2	122.9 (11)	C19—C18—H18	121.3 (13)
C1—C2—H2	118.0 (11)	C17—C18—H18	120.4 (12)
C2—C3—C4	121.33 (17)	C20—C19—C18	121.16 (19)
C2—C3—H3	118.2 (12)	C20—C19—H19	122.3 (13)
C4—C3—H3	120.5 (12)	C18—C19—H19	116.5 (13)
C5—C4—C3	120.89 (17)	C21—C20—C19	121.61 (18)
C5—C4—H4	119.2 (12)	C21—C20—H20	119.4 (13)
C3—C4—H4	119.9 (12)	C19—C20—H20	119.0 (13)
C4—C5—C6	118.28 (17)	C20—C21—C22	117.70 (19)
C4—C5—H5	121.3 (13)	C20—C21—H21	121.9 (14)
C6—C5—H5	120.4 (13)	C22—C21—H21	120.4 (14)
C5—C6—C1	121.39 (15)	C17—C22—C21	121.20 (16)
C5—C6—S1	129.48 (13)	C17—C22—S2	109.35 (11)
C1—C6—S1	109.07 (12)	C21—C22—S2	129.44 (14)
N1—C7—C8	124.89 (13)	N2—C23—C24	124.47 (13)
N1—C7—S1	115.70 (12)	N2—C23—S2	115.73 (11)
C8—C7—S1	119.37 (11)	C24—C23—S2	119.80 (10)
C7—C8—C9	110.88 (13)	C23—C24—C30	110.29 (13)
C7—C8—C14	109.50 (12)	C23—C24—C25	109.11 (12)
C9—C8—C14	108.92 (13)	C30—C24—C25	109.21 (13)
C7—C8—C11	109.28 (12)	C23—C24—C27	108.63 (12)
C9—C8—C11	108.09 (13)	C30—C24—C27	110.63 (13)
C14—C8—C11	110.16 (13)	C25—C24—C27	108.93 (12)
O1—C9—C10	121.82 (17)	O2—C25—C26	122.09 (17)
O1—C9—C8	120.00 (16)	O2—C25—C24	119.67 (17)
C10—C9—C8	118.18 (14)	C26—C25—C24	118.22 (14)
C9—C10—H10A	109.5	C25—C26—H26A	109.5
C9—C10—H10B	109.5	C25—C26—H26B	109.5
H10A—C10—H10B	109.5	H26A—C26—H26B	109.5
C9—C10—H10C	109.5	C25—C26—H26C	109.5
H10A—C10—H10C	109.5	H26A—C26—H26C	109.5
H10B—C10—H10C	109.5	H26B—C26—H26C	109.5
C12—C11—C8	111.27 (14)	C28—C27—C24	112.37 (13)
C12—C11—H11A	109.4	C28—C27—H27A	109.1
C8—C11—H11A	109.4	C24—C27—H27A	109.1
C12—C11—H11B	109.4	C28—C27—H27B	109.1
C8—C11—H11B	109.4	C24—C27—H27B	109.1
H11A—C11—H11B	108.0	H27A—C27—H27B	107.9
C13—C12—C11	176.8 (2)	C29—C28—C27	178.3 (3)
C12—C13—H13	179.2 (18)	C28—C29—H29	174.5 (19)
C15—C14—C8	112.10 (14)	C31—C30—C24	111.84 (14)
C15—C14—H14A	109.2	C31—C30—H30A	109.2
C8—C14—H14A	109.2	C24—C30—H30A	109.2
C15—C14—H14B	109.2	C31—C30—H30B	109.2
C8—C14—H14B	109.2	C24—C30—H30B	109.2
H14A—C14—H14B	107.9	H30A—C30—H30B	107.9
C16—C15—C14	178.6 (2)	C32—C31—C30	176.8 (2)
C15—C16—H16	177.2 (18)	C31—C32—H32	177.4 (19)
C7—N1—C1—C2	−177.23 (16)	C23—N2—C17—C18	179.57 (17)
C7—N1—C1—C6	0.27 (19)	C23—N2—C17—C22	0.14 (19)
N1—C1—C2—C3	176.44 (16)	N2—C17—C18—C19	−178.52 (18)
C6—C1—C2—C3	−1.0 (3)	C22—C17—C18—C19	0.9 (3)
C1—C2—C3—C4	0.4 (3)	C17—C18—C19—C20	−0.1 (3)
C2—C3—C4—C5	0.7 (3)	C18—C19—C20—C21	−0.9 (4)
C3—C4—C5—C6	−1.1 (3)	C19—C20—C21—C22	1.0 (3)
C4—C5—C6—C1	0.5 (3)	N2—C17—C22—C21	178.71 (15)
C4—C5—C6—S1	−176.61 (15)	C18—C17—C22—C21	−0.7 (3)
N1—C1—C6—C5	−177.15 (15)	N2—C17—C22—S2	−0.31 (17)
C2—C1—C6—C5	0.5 (2)	C18—C17—C22—S2	−179.77 (14)
N1—C1—C6—S1	0.50 (17)	C20—C21—C22—C17	−0.2 (3)
C2—C1—C6—S1	178.18 (13)	C20—C21—C22—S2	178.59 (15)
C7—S1—C6—C5	176.60 (17)	C23—S2—C22—C17	0.29 (12)
C7—S1—C6—C1	−0.80 (12)	C23—S2—C22—C21	−178.63 (16)
C1—N1—C7—C8	176.84 (13)	C17—N2—C23—C24	179.44 (13)
C1—N1—C7—S1	−0.94 (17)	C17—N2—C23—S2	0.10 (17)
C6—S1—C7—N1	1.05 (13)	C22—S2—C23—N2	−0.24 (13)
C6—S1—C7—C8	−176.85 (12)	C22—S2—C23—C24	−179.61 (12)
N1—C7—C8—C9	112.90 (17)	N2—C23—C24—C30	127.53 (16)
S1—C7—C8—C9	−69.40 (15)	S2—C23—C24—C30	−53.15 (16)
N1—C7—C8—C14	−126.88 (16)	N2—C23—C24—C25	−112.51 (16)
S1—C7—C8—C14	50.82 (16)	S2—C23—C24—C25	66.81 (15)
N1—C7—C8—C11	−6.1 (2)	N2—C23—C24—C27	6.1 (2)
S1—C7—C8—C11	171.56 (11)	S2—C23—C24—C27	−174.56 (11)
C7—C8—C9—O1	131.63 (17)	C23—C24—C25—O2	−126.98 (16)
C14—C8—C9—O1	11.1 (2)	C30—C24—C25—O2	−6.3 (2)
C11—C8—C9—O1	−108.61 (18)	C27—C24—C25—O2	114.58 (17)
C7—C8—C9—C10	−49.44 (19)	C23—C24—C25—C26	54.16 (19)
C14—C8—C9—C10	−170.00 (15)	C30—C24—C25—C26	174.79 (15)
C11—C8—C9—C10	70.32 (18)	C27—C24—C25—C26	−64.29 (19)
C7—C8—C11—C12	−175.71 (14)	C23—C24—C27—C28	179.97 (15)
C9—C8—C11—C12	63.53 (18)	C30—C24—C27—C28	58.76 (19)
C14—C8—C11—C12	−55.37 (18)	C25—C24—C27—C28	−61.29 (19)
C8—C11—C12—C13	22 (4)	C24—C27—C28—C29	−68 (7)
C7—C8—C14—C15	56.19 (18)	C23—C24—C30—C31	−58.50 (18)
C9—C8—C14—C15	177.59 (14)	C25—C24—C30—C31	−178.41 (14)
C11—C8—C14—C15	−64.02 (18)	C27—C24—C30—C31	61.71 (18)
C8—C14—C15—C16	−35 (10)	C24—C30—C31—C32	−26 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C13—–H13···..O1i	0.93 (3)	2.52 (3)	3.409 (3)	161 (2)
C14—–H14B···..O2	0.97	2.39	3.302 (2)	155
C27—–H27A···..O1ii	0.97	2.55	3.409 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—–H13⋯..O1i	0.93 (3)	2.52 (3)	3.409 (3)	161 (2)
C14—–H14B⋯..O2	0.97	2.39	3.302 (2)	155
C27—–H27A⋯..O1ii	0.97	2.55	3.409 (2)	147

Symmetry codes: (i) ; (ii) .