Crystal structure of methyl (2Z)-2-{[N-(2-formyl-phen-yl)-4-methyl-benzene-sulfonamido]-meth-yl}-3-(4-meth-oxy-phen-yl)prop-2-enoate.

In the title compound, C26H25NO6S, the S atom shows a distorted tetra-hedral geometry, with O-S-O [119.46 (9)°] and N-S-C [107.16 (7)°] angles deviating from ideal tetra-hedral values, a fact attributed to the Thorpe-Ingold effect. The sulfonyl-bound phenyl ring forms dihedral angles of 41.1 (1) and 83.3 (1)°, respectively, with the formyl-phenyl and phenyl rings. The dihedral angle between formyl-phenyl and phenyl rings is 47.6 (1)°. The crystal packing features C-H⋯O hydrogen-bond inter-actions.

Related literature

For background to the pharmacological uses of sulfonamides, see: Korolkovas et al. (1988 ▸); Mandell & Sande (1992 ▸). For the anti­filarial activity of sulfonamide derivatives, see: Radembino et al. (1997 ▸); For related structures, see: Ranjith et al. (2009 ▸); Madhanraj et al. (2011 ▸). For the Thorpe–Ingold effect, see: Bassindale et al. (1984 ▸).

Experimental

Crystal data

C26H25NO6S

M = 479.53

Triclinic,

a = 8.3501 (2) Å

b = 8.4859 (2) Å

c = 17.6814 (4) Å

α = 84.424 (1)°

β = 80.952 (1)°

γ = 80.954 (1)°

V = 1218.52 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.17 mm−1

T = 293 K

0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2004 ▸) T min = 0.979, T max = 0.983

23816 measured reflections

5519 independent reflections

4232 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.135

S = 1.02

5519 reflections

314 parameters

13 restraints

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: APEX2 and SAINT (Bruker, 2004 ▸); data reduction: SAINT and XPREP (Bruker, 2004 ▸); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) I, 2R. DOI: 10.1107/S2056989015024172/bg2572sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015024172/bg2572Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015024172/bg2572Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015024172/bg2572fig1.tif

The mol­ecular structure of the title compound showing 30% probability displacement ellipsoids for non-H atoms

Click here for additional data file.

. DOI: 10.1107/S2056989015024172/bg2572fig2.tif

Crystal packing diagram. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

CCDC reference: 1442750

Additional supporting information: crystallographic information; 3D view; checkCIF report

C26H25NO6S	Z = 2
Mr = 479.53	F(000) = 504
Triclinic, P1	Dx = 1.307 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3501 (2) Å	Cell parameters from 8834 reflections
b = 8.4859 (2) Å	θ = 2.6–31.2°
c = 17.6814 (4) Å	µ = 0.17 mm−1
α = 84.424 (1)°	T = 293 K
β = 80.952 (1)°	Block, colourless
γ = 80.954 (1)°	0.25 × 0.20 × 0.20 mm
V = 1218.52 (5) Å3

Bruker Kappa APEXII CCD diffractometer	5519 independent reflections
Radiation source: fine-focus sealed tube	4232 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scan	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker 2004)	h = −10→10
Tmin = 0.979, Tmax = 0.983	k = −11→11
23816 measured reflections	l = −22→22

Refinement on F2	13 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.0713P)2 + 0.275P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
5519 reflections	Δρmax = 0.34 e Å−3
314 parameters	Δρmin = −0.36 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	Occ. (<1)
S1	0.89631 (5)	0.51292 (5)	0.33325 (2)	0.04835 (15)
O1A	1.4384 (2)	0.5552 (4)	0.2246 (2)	0.1151 (13)	0.740 (4)
H7A	1.2277	0.5012	0.2267	0.080*	0.740 (4)
O1B	1.3729 (9)	0.4953 (8)	0.2764 (4)	0.1151 (13)	0.260 (4)
H7B	1.2365	0.5460	0.1946	0.080*	0.260 (4)
O2	0.82045 (18)	0.40111 (14)	0.30104 (8)	0.0609 (4)
O3	1.04550 (18)	0.46004 (16)	0.36347 (8)	0.0696 (4)
O4	1.35510 (18)	0.15273 (16)	0.03718 (9)	0.0700 (4)
O5	0.83811 (19)	1.06484 (15)	0.08082 (8)	0.0693 (4)
O6	0.66997 (15)	1.02738 (14)	0.18898 (7)	0.0565 (3)
N1	0.93431 (15)	0.65272 (14)	0.26408 (7)	0.0379 (3)
C1	1.03147 (19)	0.76893 (18)	0.27928 (9)	0.0396 (3)
C2	0.9569 (2)	0.9142 (2)	0.30551 (11)	0.0525 (4)
H2	0.8432	0.9362	0.3149	0.063*
C3	1.0505 (3)	1.0272 (2)	0.31794 (13)	0.0677 (6)
H3	0.9996	1.1253	0.3352	0.081*
C4	1.2173 (3)	0.9952 (3)	0.30501 (14)	0.0720 (6)
H4	1.2801	1.0710	0.3139	0.086*
C5	1.2920 (2)	0.8516 (3)	0.27898 (12)	0.0651 (5)
H5	1.4059	0.8307	0.2703	0.078*
C6	1.2016 (2)	0.7363 (2)	0.26528 (10)	0.0494 (4)
C7	1.2889 (2)	0.5845 (3)	0.23465 (13)	0.0674 (6)
C8	0.7539 (2)	0.6044 (2)	0.40537 (9)	0.0493 (4)
C9	0.5901 (2)	0.6237 (2)	0.39958 (11)	0.0587 (5)
H9	0.5535	0.5855	0.3588	0.070*
C10	0.4797 (3)	0.7018 (3)	0.45622 (13)	0.0703 (6)
H10	0.3682	0.7165	0.4528	0.084*
C11	0.5324 (3)	0.7579 (2)	0.51727 (12)	0.0702 (6)
C12	0.6966 (4)	0.7339 (3)	0.52188 (13)	0.0793 (7)
H12	0.7333	0.7691	0.5634	0.095*
C13	0.8076 (3)	0.6594 (3)	0.46667 (11)	0.0678 (6)
H13	0.9190	0.6457	0.4703	0.081*
C14	0.4101 (4)	0.8423 (3)	0.57835 (16)	0.1047 (10)
H14A	0.3053	0.8683	0.5608	0.157*
H14B	0.4473	0.9388	0.5882	0.157*
H14C	0.4002	0.7734	0.6247	0.157*
C15	0.79663 (18)	0.71501 (18)	0.22006 (9)	0.0401 (3)
H15A	0.7147	0.7856	0.2509	0.048*
H15B	0.7455	0.6265	0.2089	0.048*
C16	0.85673 (19)	0.80473 (18)	0.14613 (9)	0.0392 (3)
C17	0.9703 (2)	0.74544 (19)	0.08975 (9)	0.0430 (4)
H17	0.9941	0.8196	0.0488	0.052*
C18	1.0633 (2)	0.58688 (19)	0.08059 (9)	0.0424 (4)
C19	1.2034 (2)	0.5730 (2)	0.02594 (10)	0.0524 (4)
H19	1.2334	0.6645	−0.0027	0.063*
C20	1.2982 (2)	0.4287 (2)	0.01316 (12)	0.0587 (5)
H20	1.3920	0.4232	−0.0232	0.070*
C21	1.2547 (2)	0.2907 (2)	0.05425 (11)	0.0507 (4)
C22	1.1149 (2)	0.2998 (2)	0.10759 (10)	0.0521 (4)
H22	1.0840	0.2076	0.1351	0.062*
C23	1.0211 (2)	0.4462 (2)	0.12001 (10)	0.0489 (4)
H23	0.9265	0.4510	0.1559	0.059*
C24	1.3116 (3)	0.0075 (2)	0.07567 (14)	0.0790 (7)
H24A	1.3916	−0.0803	0.0580	0.119*
H24B	1.2059	−0.0071	0.0650	0.119*
H24C	1.3080	0.0117	0.1300	0.119*
C25	0.7907 (2)	0.97716 (19)	0.13359 (9)	0.0445 (4)
C26	0.6048 (3)	1.1955 (2)	0.18269 (14)	0.0693 (6)
H26A	0.5197	1.2190	0.2250	0.104*
H26B	0.5607	1.2211	0.1353	0.104*
H26C	0.6908	1.2579	0.1836	0.104*

	U11	U22	U33	U12	U13	U23
S1	0.0578 (3)	0.0350 (2)	0.0469 (2)	0.00262 (17)	−0.00629 (19)	0.00590 (16)
O1A	0.0336 (12)	0.118 (2)	0.199 (3)	0.0111 (12)	−0.0125 (15)	−0.082 (2)
O1B	0.0336 (12)	0.118 (2)	0.199 (3)	0.0111 (12)	−0.0125 (15)	−0.082 (2)
O2	0.0854 (10)	0.0349 (6)	0.0604 (8)	−0.0140 (6)	−0.0004 (7)	−0.0018 (5)
O3	0.0716 (9)	0.0610 (8)	0.0674 (8)	0.0168 (7)	−0.0208 (7)	0.0137 (7)
O4	0.0663 (9)	0.0500 (7)	0.0866 (10)	0.0013 (6)	0.0017 (8)	−0.0059 (7)
O5	0.0902 (10)	0.0450 (7)	0.0628 (8)	−0.0074 (7)	0.0068 (7)	0.0127 (6)
O6	0.0576 (8)	0.0441 (6)	0.0602 (8)	0.0031 (5)	−0.0009 (6)	0.0047 (6)
N1	0.0368 (7)	0.0346 (6)	0.0406 (7)	−0.0006 (5)	−0.0064 (5)	0.0006 (5)
C1	0.0417 (8)	0.0379 (7)	0.0383 (8)	−0.0002 (6)	−0.0089 (6)	−0.0023 (6)
C2	0.0524 (10)	0.0443 (9)	0.0589 (11)	0.0044 (7)	−0.0095 (8)	−0.0106 (8)
C3	0.0856 (16)	0.0428 (10)	0.0773 (14)	−0.0027 (9)	−0.0198 (12)	−0.0158 (9)
C4	0.0803 (16)	0.0650 (13)	0.0815 (15)	−0.0261 (11)	−0.0252 (12)	−0.0128 (11)
C5	0.0493 (11)	0.0781 (14)	0.0737 (13)	−0.0138 (10)	−0.0171 (10)	−0.0125 (11)
C6	0.0417 (9)	0.0550 (10)	0.0522 (10)	0.0012 (7)	−0.0134 (8)	−0.0104 (8)
C7	0.0425 (10)	0.0754 (13)	0.0857 (15)	0.0117 (9)	−0.0194 (10)	−0.0296 (11)
C8	0.0617 (11)	0.0423 (8)	0.0395 (9)	−0.0038 (7)	−0.0039 (8)	0.0074 (7)
C9	0.0653 (12)	0.0546 (10)	0.0525 (10)	−0.0110 (9)	−0.0007 (9)	0.0058 (8)
C10	0.0643 (13)	0.0620 (12)	0.0742 (14)	−0.0079 (10)	0.0090 (11)	0.0136 (10)
C11	0.0995 (18)	0.0490 (10)	0.0504 (11)	−0.0066 (11)	0.0152 (11)	0.0061 (9)
C12	0.111 (2)	0.0733 (14)	0.0500 (12)	−0.0041 (13)	−0.0071 (12)	−0.0084 (10)
C13	0.0805 (15)	0.0700 (13)	0.0512 (11)	−0.0029 (11)	−0.0138 (10)	−0.0026 (10)
C14	0.134 (2)	0.0742 (16)	0.0836 (17)	−0.0069 (16)	0.0461 (17)	−0.0058 (14)
C15	0.0339 (8)	0.0409 (8)	0.0436 (8)	−0.0044 (6)	−0.0060 (6)	0.0047 (6)
C16	0.0403 (8)	0.0395 (8)	0.0402 (8)	−0.0108 (6)	−0.0108 (7)	0.0022 (6)
C17	0.0499 (9)	0.0417 (8)	0.0394 (8)	−0.0138 (7)	−0.0086 (7)	0.0019 (6)
C18	0.0479 (9)	0.0440 (8)	0.0383 (8)	−0.0126 (7)	−0.0085 (7)	−0.0042 (6)
C19	0.0540 (10)	0.0483 (9)	0.0529 (10)	−0.0127 (8)	0.0003 (8)	0.0023 (8)
C20	0.0481 (10)	0.0584 (11)	0.0652 (12)	−0.0090 (8)	0.0068 (9)	−0.0041 (9)
C21	0.0499 (10)	0.0464 (9)	0.0566 (10)	−0.0042 (7)	−0.0105 (8)	−0.0086 (8)
C22	0.0659 (12)	0.0416 (8)	0.0501 (10)	−0.0156 (8)	−0.0054 (8)	−0.0033 (7)
C23	0.0554 (10)	0.0464 (9)	0.0452 (9)	−0.0158 (7)	0.0026 (8)	−0.0075 (7)
C24	0.0998 (18)	0.0466 (11)	0.0829 (15)	−0.0004 (11)	0.0001 (13)	−0.0043 (10)
C25	0.0486 (9)	0.0414 (8)	0.0442 (9)	−0.0079 (7)	−0.0102 (7)	0.0013 (7)
C26	0.0743 (14)	0.0447 (10)	0.0818 (14)	0.0054 (9)	−0.0061 (11)	−0.0011 (9)

S1—O3	1.4233 (14)	C11—C12	1.368 (3)
S1—O2	1.4259 (14)	C11—C14	1.515 (3)
S1—N1	1.6486 (13)	C12—C13	1.365 (3)
S1—C8	1.7517 (18)	C12—H12	0.9300
O1A—C7	1.222 (3)	C13—H13	0.9300
O1B—C7	1.223 (3)	C14—H14A	0.9600
O4—C21	1.359 (2)	C14—H14B	0.9600
O4—C24	1.419 (3)	C14—H14C	0.9600
O5—C25	1.193 (2)	C15—C16	1.504 (2)
O6—C25	1.339 (2)	C15—H15A	0.9700
O6—C26	1.445 (2)	C15—H15B	0.9700
N1—C1	1.440 (2)	C16—C17	1.340 (2)
N1—C15	1.4891 (18)	C16—C25	1.489 (2)
C1—C2	1.379 (2)	C17—C18	1.454 (2)
C1—C6	1.391 (2)	C17—H17	0.9300
C2—C3	1.382 (3)	C18—C23	1.389 (2)
C2—H2	0.9300	C18—C19	1.392 (2)
C3—C4	1.363 (3)	C19—C20	1.368 (3)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.366 (3)	C20—C21	1.384 (3)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.386 (3)	C21—C22	1.377 (3)
C5—H5	0.9300	C22—C23	1.378 (2)
C6—C7	1.483 (3)	C22—H22	0.9300
C7—H7A	0.9672	C23—H23	0.9300
C7—H7B	0.9933	C24—H24A	0.9600
C8—C9	1.371 (3)	C24—H24B	0.9600
C8—C13	1.383 (3)	C24—H24C	0.9600
C9—C10	1.392 (3)	C26—H26A	0.9600
C9—H9	0.9300	C26—H26B	0.9600
C10—C11	1.378 (3)	C26—H26C	0.9600
C10—H10	0.9300
O3—S1—O2	119.46 (9)	C8—C13—H13	120.1
O3—S1—N1	106.81 (8)	C11—C14—H14A	109.5
O2—S1—N1	106.18 (7)	C11—C14—H14B	109.5
O3—S1—C8	108.18 (9)	H14A—C14—H14B	109.5
O2—S1—C8	108.44 (9)	C11—C14—H14C	109.5
N1—S1—C8	107.16 (7)	H14A—C14—H14C	109.5
C21—O4—C24	117.95 (16)	H14B—C14—H14C	109.5
C25—O6—C26	116.06 (14)	N1—C15—C16	110.86 (12)
C1—N1—C15	116.00 (11)	N1—C15—H15A	109.5
C1—N1—S1	116.79 (10)	C16—C15—H15A	109.5
C15—N1—S1	115.48 (10)	N1—C15—H15B	109.5
C2—C1—C6	119.77 (16)	C16—C15—H15B	109.5
C2—C1—N1	120.41 (14)	H15A—C15—H15B	108.1
C6—C1—N1	119.79 (14)	C17—C16—C25	115.34 (14)
C1—C2—C3	120.25 (18)	C17—C16—C15	126.06 (14)
C1—C2—H2	119.9	C25—C16—C15	118.56 (14)
C3—C2—H2	119.9	C16—C17—C18	132.06 (14)
C4—C3—C2	120.22 (18)	C16—C17—H17	114.0
C4—C3—H3	119.9	C18—C17—H17	114.0
C2—C3—H3	119.9	C23—C18—C19	116.85 (15)
C3—C4—C5	119.86 (19)	C23—C18—C17	125.39 (15)
C3—C4—H4	120.1	C19—C18—C17	117.72 (15)
C5—C4—H4	120.1	C20—C19—C18	121.79 (16)
C4—C5—C6	121.33 (19)	C20—C19—H19	119.1
C4—C5—H5	119.3	C18—C19—H19	119.1
C6—C5—H5	119.3	C19—C20—C21	120.10 (17)
C5—C6—C1	118.57 (16)	C19—C20—H20	119.9
C5—C6—C7	119.11 (17)	C21—C20—H20	119.9
C1—C6—C7	122.31 (16)	O4—C21—C22	124.42 (17)
O1A—C7—C6	121.8 (2)	O4—C21—C20	115.99 (17)
O1B—C7—C6	117.2 (4)	C22—C21—C20	119.57 (16)
O1A—C7—H7A	118.0	C21—C22—C23	119.62 (16)
C6—C7—H7A	120.0	C21—C22—H22	120.2
O1B—C7—H7B	123.3	C23—C22—H22	120.2
C6—C7—H7B	114.0	C22—C23—C18	122.03 (16)
C9—C8—C13	120.62 (18)	C22—C23—H23	119.0
C9—C8—S1	119.52 (15)	C18—C23—H23	119.0
C13—C8—S1	119.85 (16)	O4—C24—H24A	109.5
C8—C9—C10	118.4 (2)	O4—C24—H24B	109.5
C8—C9—H9	120.8	H24A—C24—H24B	109.5
C10—C9—H9	120.8	O4—C24—H24C	109.5
C11—C10—C9	121.3 (2)	H24A—C24—H24C	109.5
C11—C10—H10	119.4	H24B—C24—H24C	109.5
C9—C10—H10	119.4	O5—C25—O6	122.00 (15)
C12—C11—C10	118.6 (2)	O5—C25—C16	125.15 (16)
C12—C11—C14	121.0 (2)	O6—C25—C16	112.85 (13)
C10—C11—C14	120.4 (3)	O6—C26—H26A	109.5
C13—C12—C11	121.3 (2)	O6—C26—H26B	109.5
C13—C12—H12	119.4	H26A—C26—H26B	109.5
C11—C12—H12	119.4	O6—C26—H26C	109.5
C12—C13—C8	119.7 (2)	H26A—C26—H26C	109.5
C12—C13—H13	120.1	H26B—C26—H26C	109.5
O3—S1—N1—C1	−43.28 (13)	C9—C10—C11—C12	−0.7 (3)
O2—S1—N1—C1	−171.79 (11)	C9—C10—C11—C14	−179.89 (19)
C8—S1—N1—C1	72.47 (13)	C10—C11—C12—C13	1.5 (3)
O3—S1—N1—C15	175.04 (11)	C14—C11—C12—C13	−179.3 (2)
O2—S1—N1—C15	46.53 (13)	C11—C12—C13—C8	−1.1 (3)
C8—S1—N1—C15	−69.21 (13)	C9—C8—C13—C12	−0.1 (3)
C15—N1—C1—C2	45.8 (2)	S1—C8—C13—C12	178.51 (16)
S1—N1—C1—C2	−95.71 (16)	C1—N1—C15—C16	54.01 (17)
C15—N1—C1—C6	−132.35 (15)	S1—N1—C15—C16	−164.00 (11)
S1—N1—C1—C6	86.17 (16)	N1—C15—C16—C17	58.9 (2)
C6—C1—C2—C3	0.0 (3)	N1—C15—C16—C25	−118.85 (15)
N1—C1—C2—C3	−178.15 (16)	C25—C16—C17—C18	179.51 (16)
C1—C2—C3—C4	−0.6 (3)	C15—C16—C17—C18	1.7 (3)
C2—C3—C4—C5	0.6 (4)	C16—C17—C18—C23	19.7 (3)
C3—C4—C5—C6	0.0 (4)	C16—C17—C18—C19	−162.71 (17)
C4—C5—C6—C1	−0.6 (3)	C23—C18—C19—C20	−2.0 (3)
C4—C5—C6—C7	178.0 (2)	C17—C18—C19—C20	−179.77 (17)
C2—C1—C6—C5	0.6 (3)	C18—C19—C20—C21	0.9 (3)
N1—C1—C6—C5	178.73 (16)	C24—O4—C21—C22	1.3 (3)
C2—C1—C6—C7	−177.97 (18)	C24—O4—C21—C20	−177.5 (2)
N1—C1—C6—C7	0.2 (3)	C19—C20—C21—O4	179.36 (18)
C5—C6—C7—O1A	3.6 (4)	C19—C20—C21—C22	0.5 (3)
C1—C6—C7—O1A	−177.9 (3)	O4—C21—C22—C23	−179.51 (17)
C5—C6—C7—O1B	66.3 (5)	C20—C21—C22—C23	−0.7 (3)
C1—C6—C7—O1B	−115.1 (5)	C21—C22—C23—C18	−0.4 (3)
O3—S1—C8—C9	−161.09 (14)	C19—C18—C23—C22	1.7 (3)
O2—S1—C8—C9	−30.16 (15)	C17—C18—C23—C22	179.32 (16)
N1—S1—C8—C9	84.07 (15)	C26—O6—C25—O5	−2.3 (3)
O3—S1—C8—C13	20.28 (17)	C26—O6—C25—C16	177.19 (15)
O2—S1—C8—C13	151.21 (15)	C17—C16—C25—O5	−4.8 (3)
N1—S1—C8—C13	−94.56 (15)	C15—C16—C25—O5	173.22 (17)
C13—C8—C9—C10	0.9 (3)	C17—C16—C25—O6	175.70 (14)
S1—C8—C9—C10	−177.74 (13)	C15—C16—C25—O6	−6.3 (2)
C8—C9—C10—C11	−0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1Bi	0.93	2.50	3.397 (7)	162
C15—H15A···O6	0.97	2.24	2.7322 (19)	111
C24—H24A···O4ii	0.96	2.52	3.341 (3)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1B i	0.93	2.50	3.397 (7)	162
C15—H15A⋯O6	0.97	2.24	2.7322 (19)	111
C24—H24A⋯O4ii	0.96	2.52	3.341 (3)	143

Symmetry codes: (i) ; (ii) .