N-Ethyl-4-methyl-N-(3-methyl-phen-yl)benzene-sulfonamide.

The title compound, C(16)H(19)NO(2)S, crystallizes with two crystallographically independent mol-ecules in the asymmetric unit in which the dihedral angles between the planes defined by the aromatic rings are 35.3 (2) and 42.5 (2)°. In the crystal, inter-molecular C-H⋯O hydrogen bonds stabilize the packing.

Related literature

For medicinal and pharmacological uses of sulfonamides, see: Betts et al. (2003 ▶); Brown (2000 ▶); Collery et al. (2008 ▶); Jones et al. (1997 ▶); Smolin et al. (1994 ▶). For related structures, see: Ahmad et al. (2011 ▶); Aziz-ur-Rehman et al. (2010a ▶,b ▶,c ▶); Khan et al. (2010 ▶).

Experimental

Crystal data

C16H19NO2S

M = 289.39

Monoclinic,

a = 19.753 (1) Å

b = 8.335 (1) Å

c = 20.395 (2) Å

β = 108.657 (3)°

V = 3181.4 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.20 mm−1

T = 296 K

0.25 × 0.13 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

24592 measured reflections

5905 independent reflections

2779 reflections with I > 2σ(I)

R int = 0.087

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.173

S = 0.99

5905 reflections

366 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681102589X/bt5567sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102589X/bt5567Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681102589X/bt5567Isup3.cml

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

C16H19NO2S	F(000) = 1232
Mr = 289.39	Dx = 1.208 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2536 reflections
a = 19.753 (1) Å	θ = 3.1–19.5°
b = 8.335 (1) Å	µ = 0.20 mm−1
c = 20.395 (2) Å	T = 296 K
β = 108.657 (3)°	Needle, colourless
V = 3181.4 (4) Å3	0.25 × 0.13 × 0.09 mm
Z = 8

Bruker APEXII CCD diffractometer	2779 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.087
graphite	θmax = 25.5°, θmin = 1.3°
φ and ω scans	h = −23→23
24592 measured reflections	k = −8→10
5905 independent 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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.073P)2] where P = (Fo2 + 2Fc2)/3
5905 reflections	(Δ/σ)max < 0.001
366 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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)
S2	0.30839 (5)	0.21131 (11)	0.33137 (6)	0.0586 (4)
O3	0.34832 (13)	0.0725 (3)	0.36279 (15)	0.0732 (12)
O4	0.30175 (14)	0.2502 (3)	0.26194 (15)	0.0764 (11)
N2	0.22738 (14)	0.1862 (3)	0.33484 (16)	0.0528 (10)
C17	0.4182 (3)	0.7947 (6)	0.5085 (3)	0.130 (3)
C18	0.3931 (2)	0.6476 (6)	0.4640 (3)	0.0804 (19)
C19	0.3549 (2)	0.6621 (5)	0.3957 (3)	0.0792 (19)
C20	0.3303 (2)	0.5302 (5)	0.3542 (2)	0.0686 (17)
C21	0.34449 (18)	0.3789 (4)	0.3824 (2)	0.0549 (14)
C22	0.3833 (2)	0.3611 (5)	0.4506 (2)	0.0735 (19)
C23	0.4077 (2)	0.4953 (6)	0.4911 (2)	0.0874 (19)
C24	0.17367 (19)	0.3093 (5)	0.3030 (2)	0.0706 (17)
C25	0.0997 (2)	0.2383 (6)	0.2796 (3)	0.100 (2)
C26	0.22070 (16)	0.1089 (4)	0.3956 (2)	0.0492 (14)
C27	0.20519 (18)	−0.0524 (4)	0.3917 (2)	0.0587 (14)
C28	0.1949 (2)	−0.1317 (5)	0.4468 (2)	0.0715 (19)
C29	0.2020 (2)	−0.0471 (5)	0.5064 (2)	0.0761 (17)
C30	0.2180 (2)	0.1138 (5)	0.5109 (2)	0.0770 (17)
C31	0.2264 (2)	0.1913 (4)	0.4553 (2)	0.0634 (16)
C32	0.1764 (3)	−0.3090 (5)	0.4404 (3)	0.127 (3)
S1	−0.16509 (5)	−0.14051 (12)	0.31425 (6)	0.0648 (4)
O1	−0.23579 (13)	−0.0975 (3)	0.31230 (16)	0.0877 (13)
O2	−0.13463 (14)	−0.2857 (3)	0.34707 (15)	0.0786 (11)
N1	−0.16606 (15)	−0.1498 (4)	0.23453 (17)	0.0619 (13)
C1	0.0351 (3)	0.4102 (8)	0.4320 (4)	0.190 (4)
C2	−0.0154 (4)	0.2711 (8)	0.4058 (4)	0.111 (3)
C3	−0.0847 (4)	0.2978 (6)	0.3656 (3)	0.111 (3)
C4	−0.1314 (2)	0.1734 (5)	0.3393 (3)	0.0856 (19)
C5	−0.1080 (2)	0.0180 (5)	0.3528 (2)	0.0634 (17)
C6	−0.0396 (2)	−0.0099 (6)	0.3931 (2)	0.0838 (19)
C7	0.0056 (3)	0.1178 (8)	0.4193 (3)	0.108 (3)
C8	−0.1985 (3)	−0.0114 (6)	0.1890 (3)	0.105 (2)
C9	−0.2221 (3)	−0.0469 (7)	0.1165 (3)	0.130 (3)
C10	−0.10618 (19)	−0.2300 (5)	0.2214 (2)	0.0613 (16)
C11	−0.11588 (18)	−0.3812 (5)	0.1959 (2)	0.0623 (16)
C12	−0.0620 (2)	−0.4620 (5)	0.1791 (2)	0.0683 (16)
C13	0.0024 (2)	−0.3826 (6)	0.1910 (2)	0.0801 (19)
C14	0.0117 (2)	−0.2301 (6)	0.2176 (3)	0.098 (2)
C15	−0.0421 (2)	−0.1498 (5)	0.2321 (2)	0.0819 (19)
C16	−0.0740 (2)	−0.6272 (5)	0.1484 (3)	0.105 (2)
H17A	0.44420	0.76230	0.55490	0.1960*	0.500
H17B	0.37760	0.85780	0.50870	0.1960*	0.500
H17C	0.44870	0.85740	0.49010	0.1960*	0.500
H17D	0.40280	0.88940	0.48090	0.1960*	0.500
H17E	0.46940	0.79390	0.52710	0.1960*	0.500
H17F	0.39830	0.79430	0.54570	0.1960*	0.500
H19	0.34520	0.76400	0.37640	0.0950*
H20	0.30420	0.54320	0.30770	0.0820*
H22	0.39320	0.25910	0.46980	0.0880*
H23	0.43450	0.48260	0.53750	0.1050*
H24A	0.18390	0.35580	0.26360	0.0850*
H24B	0.17610	0.39410	0.33620	0.0850*
H25A	0.09640	0.15890	0.24470	0.1500*
H25B	0.06530	0.32150	0.26100	0.1500*
H25C	0.09010	0.18930	0.31830	0.1500*
H27	0.20160	−0.10850	0.35130	0.0700*
H29	0.19580	−0.09950	0.54430	0.0910*
H30	0.22310	0.16940	0.55170	0.0920*
H31	0.23610	0.30080	0.45780	0.0760*
H32A	0.21940	−0.37110	0.45770	0.1900*
H32B	0.15280	−0.33510	0.39270	0.1900*
H32C	0.14520	−0.33280	0.46690	0.1900*
H1A	0.04570	0.45970	0.39390	0.2840*
H1B	0.07860	0.37190	0.46500	0.2840*
H1C	0.01320	0.48750	0.45380	0.2840*
H3	−0.10060	0.40280	0.35570	0.1320*
H4	−0.17840	0.19440	0.31270	0.1030*
H6	−0.02330	−0.11460	0.40290	0.1010*
H7	0.05220	0.09690	0.44730	0.1300*
H8A	−0.23900	0.02740	0.20160	0.1250*
H8B	−0.16370	0.07460	0.19760	0.1250*
H9A	−0.18240	−0.08390	0.10320	0.1950*
H9B	−0.24170	0.04820	0.09090	0.1950*
H9C	−0.25820	−0.12880	0.10690	0.1950*
H11	−0.15940	−0.43210	0.18950	0.0750*
H13	0.03980	−0.43340	0.18080	0.0960*
H14	0.05580	−0.18000	0.22590	0.1180*
H15	−0.03590	−0.04500	0.24870	0.0980*
H16A	−0.03600	−0.65380	0.13050	0.1570*
H16B	−0.11880	−0.63020	0.11170	0.1570*
H16C	−0.07480	−0.70320	0.18350	0.1570*

	U11	U22	U33	U12	U13	U23
S2	0.0635 (6)	0.0536 (6)	0.0688 (8)	−0.0062 (5)	0.0353 (5)	−0.0012 (5)
O3	0.0685 (16)	0.0485 (15)	0.114 (3)	0.0114 (12)	0.0454 (16)	0.0103 (15)
O4	0.095 (2)	0.0828 (19)	0.064 (2)	−0.0249 (14)	0.0430 (16)	−0.0084 (15)
N2	0.0544 (17)	0.0501 (17)	0.058 (2)	−0.0003 (14)	0.0239 (15)	0.0074 (15)
C17	0.142 (5)	0.115 (4)	0.122 (5)	−0.030 (4)	0.025 (4)	−0.050 (4)
C18	0.080 (3)	0.082 (3)	0.077 (4)	−0.019 (2)	0.022 (3)	−0.017 (3)
C19	0.097 (3)	0.052 (3)	0.081 (4)	−0.004 (2)	0.018 (3)	−0.004 (3)
C20	0.079 (3)	0.062 (3)	0.059 (3)	−0.005 (2)	0.014 (2)	0.008 (2)
C21	0.054 (2)	0.056 (2)	0.055 (3)	−0.0028 (17)	0.018 (2)	0.010 (2)
C22	0.069 (3)	0.071 (3)	0.071 (4)	−0.004 (2)	0.009 (2)	0.013 (3)
C23	0.083 (3)	0.106 (4)	0.059 (3)	−0.014 (3)	0.003 (2)	0.003 (3)
C24	0.071 (3)	0.069 (3)	0.070 (3)	0.010 (2)	0.020 (2)	0.012 (2)
C25	0.063 (3)	0.127 (4)	0.101 (4)	0.010 (3)	0.013 (3)	0.020 (3)
C26	0.048 (2)	0.046 (2)	0.059 (3)	−0.0017 (16)	0.0247 (19)	0.0014 (19)
C27	0.070 (2)	0.049 (2)	0.064 (3)	−0.0039 (18)	0.031 (2)	−0.006 (2)
C28	0.086 (3)	0.057 (3)	0.079 (4)	−0.012 (2)	0.037 (3)	0.002 (2)
C29	0.095 (3)	0.080 (3)	0.063 (3)	−0.007 (2)	0.039 (3)	0.010 (3)
C30	0.105 (3)	0.071 (3)	0.068 (3)	−0.017 (2)	0.046 (3)	−0.014 (2)
C31	0.077 (3)	0.048 (2)	0.075 (3)	−0.0064 (18)	0.038 (2)	−0.008 (2)
C32	0.203 (6)	0.071 (3)	0.127 (5)	−0.042 (3)	0.082 (5)	−0.003 (3)
S1	0.0591 (6)	0.0658 (7)	0.0777 (8)	−0.0024 (5)	0.0335 (6)	0.0005 (6)
O1	0.0584 (16)	0.106 (2)	0.113 (3)	−0.0004 (14)	0.0473 (17)	−0.0134 (18)
O2	0.0895 (19)	0.0627 (17)	0.092 (2)	0.0016 (15)	0.0407 (17)	0.0167 (16)
N1	0.0506 (17)	0.067 (2)	0.073 (3)	0.0053 (15)	0.0268 (17)	0.0043 (18)
C1	0.151 (5)	0.164 (6)	0.299 (10)	−0.094 (5)	0.136 (6)	−0.138 (6)
C2	0.103 (4)	0.108 (5)	0.151 (6)	−0.043 (4)	0.080 (4)	−0.061 (4)
C3	0.132 (5)	0.070 (3)	0.157 (6)	−0.005 (3)	0.085 (5)	−0.017 (3)
C4	0.079 (3)	0.071 (3)	0.116 (4)	−0.003 (3)	0.044 (3)	−0.011 (3)
C5	0.062 (3)	0.064 (3)	0.073 (3)	0.0031 (19)	0.034 (2)	−0.002 (2)
C6	0.068 (3)	0.091 (3)	0.092 (4)	0.000 (3)	0.025 (3)	−0.001 (3)
C7	0.071 (3)	0.141 (5)	0.114 (5)	−0.022 (4)	0.031 (3)	−0.042 (4)
C8	0.089 (3)	0.133 (5)	0.083 (4)	0.036 (3)	0.015 (3)	0.015 (4)
C9	0.150 (5)	0.141 (5)	0.099 (5)	0.052 (4)	0.040 (4)	0.031 (4)
C10	0.057 (2)	0.069 (3)	0.062 (3)	−0.0093 (19)	0.025 (2)	−0.003 (2)
C11	0.046 (2)	0.065 (3)	0.075 (3)	0.0003 (19)	0.018 (2)	0.008 (2)
C12	0.060 (2)	0.069 (3)	0.076 (3)	0.001 (2)	0.022 (2)	0.004 (2)
C13	0.058 (3)	0.097 (3)	0.093 (4)	0.009 (2)	0.035 (2)	0.009 (3)
C14	0.064 (3)	0.109 (4)	0.135 (5)	−0.029 (3)	0.053 (3)	−0.029 (3)
C15	0.065 (3)	0.084 (3)	0.107 (4)	−0.021 (2)	0.042 (3)	−0.024 (3)
C16	0.080 (3)	0.084 (3)	0.142 (5)	0.014 (2)	0.025 (3)	−0.012 (3)

S2—O3	1.431 (3)	C27—H27	0.9300
S2—O4	1.417 (3)	C29—H29	0.9300
S2—N2	1.638 (3)	C30—H30	0.9300
S2—C21	1.752 (4)	C31—H31	0.9300
S1—N1	1.622 (3)	C32—H32C	0.9600
S1—O1	1.430 (3)	C32—H32A	0.9600
S1—O2	1.420 (3)	C32—H32B	0.9600
S1—C5	1.752 (4)	C1—C2	1.511 (10)
N2—C24	1.469 (5)	C2—C3	1.370 (11)
N2—C26	1.440 (5)	C2—C7	1.344 (9)
N1—C10	1.456 (5)	C3—C4	1.377 (8)
N1—C8	1.491 (6)	C4—C5	1.373 (6)
C17—C18	1.512 (7)	C5—C6	1.358 (6)
C18—C19	1.361 (8)	C6—C7	1.382 (8)
C18—C23	1.378 (7)	C8—C9	1.432 (8)
C19—C20	1.378 (6)	C10—C11	1.353 (6)
C20—C21	1.377 (5)	C10—C15	1.386 (6)
C21—C22	1.365 (5)	C11—C12	1.392 (6)
C22—C23	1.382 (6)	C12—C13	1.385 (6)
C24—C25	1.506 (6)	C12—C16	1.500 (6)
C26—C27	1.376 (5)	C13—C14	1.371 (7)
C26—C31	1.371 (5)	C14—C15	1.366 (6)
C27—C28	1.374 (5)	C1—H1A	0.9600
C28—C29	1.373 (6)	C1—H1B	0.9600
C28—C32	1.518 (6)	C1—H1C	0.9600
C29—C30	1.374 (6)	C3—H3	0.9300
C30—C31	1.361 (6)	C4—H4	0.9300
C17—H17C	0.9600	C6—H6	0.9300
C17—H17A	0.9600	C7—H7	0.9300
C17—H17B	0.9600	C8—H8A	0.9700
C17—H17F	0.9600	C8—H8B	0.9700
C17—H17D	0.9600	C9—H9A	0.9600
C17—H17E	0.9600	C9—H9B	0.9600
C19—H19	0.9300	C9—H9C	0.9600
C20—H20	0.9300	C11—H11	0.9300
C22—H22	0.9300	C13—H13	0.9300
C23—H23	0.9300	C14—H14	0.9300
C24—H24B	0.9700	C15—H15	0.9300
C24—H24A	0.9700	C16—H16A	0.9600
C25—H25C	0.9600	C16—H16B	0.9600
C25—H25B	0.9600	C16—H16C	0.9600
C25—H25A	0.9600
O3—S2—O4	119.60 (17)	H25A—C25—H25B	110.00
O3—S2—N2	106.47 (15)	H25B—C25—H25C	109.00
O3—S2—C21	108.51 (18)	C28—C27—H27	120.00
O4—S2—N2	107.04 (17)	C26—C27—H27	120.00
O4—S2—C21	107.53 (17)	C28—C29—H29	119.00
N2—S2—C21	107.09 (17)	C30—C29—H29	119.00
O1—S1—O2	119.31 (18)	C29—C30—H30	120.00
O1—S1—N1	106.61 (18)	C31—C30—H30	120.00
O1—S1—C5	107.83 (18)	C30—C31—H31	120.00
O2—S1—N1	107.41 (18)	C26—C31—H31	120.00
O2—S1—C5	108.44 (19)	C28—C32—H32B	109.00
N1—S1—C5	106.59 (18)	C28—C32—H32C	109.00
S2—N2—C26	117.0 (2)	H32A—C32—H32C	109.00
C24—N2—C26	116.2 (3)	H32B—C32—H32C	109.00
S2—N2—C24	118.0 (2)	H32A—C32—H32B	110.00
S1—N1—C8	116.9 (3)	C28—C32—H32A	109.00
S1—N1—C10	117.2 (3)	C1—C2—C3	120.5 (6)
C8—N1—C10	117.0 (4)	C1—C2—C7	122.1 (7)
C17—C18—C19	120.7 (4)	C3—C2—C7	117.4 (6)
C19—C18—C23	118.0 (4)	C2—C3—C4	121.8 (5)
C17—C18—C23	121.3 (5)	C3—C4—C5	119.4 (5)
C18—C19—C20	121.9 (4)	S1—C5—C4	119.6 (3)
C19—C20—C21	119.3 (4)	S1—C5—C6	121.0 (3)
C20—C21—C22	119.9 (3)	C4—C5—C6	119.3 (4)
S2—C21—C22	120.5 (3)	C5—C6—C7	119.8 (5)
S2—C21—C20	119.5 (3)	C2—C7—C6	122.3 (6)
C21—C22—C23	119.7 (4)	N1—C8—C9	114.6 (4)
C18—C23—C22	121.2 (4)	N1—C10—C11	118.3 (3)
N2—C24—C25	110.9 (3)	N1—C10—C15	120.3 (4)
N2—C26—C27	117.9 (3)	C11—C10—C15	121.3 (4)
N2—C26—C31	122.4 (3)	C10—C11—C12	121.3 (4)
C27—C26—C31	119.6 (3)	C11—C12—C13	117.2 (4)
C26—C27—C28	120.8 (4)	C11—C12—C16	121.1 (4)
C29—C28—C32	122.0 (4)	C13—C12—C16	121.7 (4)
C27—C28—C29	118.5 (4)	C12—C13—C14	120.8 (4)
C27—C28—C32	119.5 (4)	C13—C14—C15	121.7 (4)
C28—C29—C30	121.1 (4)	C10—C15—C14	117.7 (4)
C29—C30—C31	119.6 (4)	C2—C1—H1A	109.00
C26—C31—C30	120.3 (3)	C2—C1—H1B	110.00
C18—C17—H17C	109.00	C2—C1—H1C	110.00
C18—C17—H17D	109.00	H1A—C1—H1B	109.00
C18—C17—H17E	109.00	H1A—C1—H1C	109.00
C18—C17—H17F	109.00	H1B—C1—H1C	109.00
H17A—C17—H17B	110.00	C2—C3—H3	119.00
H17A—C17—H17C	110.00	C4—C3—H3	119.00
C18—C17—H17B	109.00	C3—C4—H4	120.00
H17C—C17—H17E	56.00	C5—C4—H4	120.00
H17C—C17—H17F	141.00	C5—C6—H6	120.00
H17D—C17—H17E	109.00	C7—C6—H6	120.00
H17D—C17—H17F	109.00	C2—C7—H7	119.00
H17E—C17—H17F	109.00	C6—C7—H7	119.00
H17B—C17—H17E	141.00	N1—C8—H8A	109.00
H17B—C17—H17F	56.00	N1—C8—H8B	109.00
H17A—C17—H17D	141.00	C9—C8—H8A	109.00
H17A—C17—H17E	56.00	C9—C8—H8B	109.00
H17A—C17—H17F	56.00	H8A—C8—H8B	108.00
H17B—C17—H17C	109.00	C8—C9—H9A	109.00
H17B—C17—H17D	56.00	C8—C9—H9B	109.00
C18—C17—H17A	109.00	C8—C9—H9C	109.00
H17C—C17—H17D	56.00	H9A—C9—H9B	110.00
C20—C19—H19	119.00	H9A—C9—H9C	110.00
C18—C19—H19	119.00	H9B—C9—H9C	109.00
C19—C20—H20	120.00	C10—C11—H11	119.00
C21—C20—H20	120.00	C12—C11—H11	119.00
C21—C22—H22	120.00	C12—C13—H13	120.00
C23—C22—H22	120.00	C14—C13—H13	120.00
C18—C23—H23	119.00	C13—C14—H14	119.00
C22—C23—H23	119.00	C15—C14—H14	119.00
N2—C24—H24A	109.00	C10—C15—H15	121.00
C25—C24—H24B	110.00	C14—C15—H15	121.00
H24A—C24—H24B	108.00	C12—C16—H16A	109.00
C25—C24—H24A	109.00	C12—C16—H16B	109.00
N2—C24—H24B	109.00	C12—C16—H16C	109.00
C24—C25—H25B	109.00	H16A—C16—H16B	110.00
C24—C25—H25A	110.00	H16A—C16—H16C	109.00
H25A—C25—H25C	109.00	H16B—C16—H16C	109.00
C24—C25—H25C	109.00
O3—S2—N2—C24	−177.3 (3)	C19—C18—C23—C22	−1.1 (7)
O3—S2—N2—C26	36.5 (3)	C17—C18—C23—C22	178.6 (4)
O4—S2—N2—C24	−48.3 (3)	C18—C19—C20—C21	0.1 (7)
O4—S2—N2—C26	165.5 (2)	C19—C20—C21—S2	175.8 (3)
C21—S2—N2—C24	66.8 (3)	C19—C20—C21—C22	−0.8 (6)
C21—S2—N2—C26	−79.4 (3)	C20—C21—C22—C23	0.5 (6)
O3—S2—C21—C20	161.0 (3)	S2—C21—C22—C23	−176.1 (3)
O4—S2—C21—C20	30.3 (4)	C21—C22—C23—C18	0.5 (6)
N2—S2—C21—C20	−84.4 (3)	N2—C26—C27—C28	−177.0 (3)
O3—S2—C21—C22	−22.4 (4)	N2—C26—C31—C30	178.4 (4)
O4—S2—C21—C22	−153.1 (3)	C31—C26—C27—C28	0.4 (6)
N2—S2—C21—C22	92.1 (3)	C27—C26—C31—C30	1.1 (6)
C5—S1—N1—C10	80.2 (3)	C26—C27—C28—C32	178.8 (4)
O2—S1—C5—C4	−168.0 (4)	C26—C27—C28—C29	−1.4 (6)
O1—S1—N1—C8	48.9 (4)	C27—C28—C29—C30	0.9 (6)
O1—S1—N1—C10	−164.9 (3)	C32—C28—C29—C30	−179.3 (4)
O2—S1—N1—C8	177.9 (3)	C28—C29—C30—C31	0.6 (6)
O2—S1—N1—C10	−35.9 (3)	C29—C30—C31—C26	−1.6 (6)
C5—S1—N1—C8	−66.1 (4)	C1—C2—C3—C4	178.1 (6)
N1—S1—C5—C4	76.7 (4)	C7—C2—C3—C4	−0.5 (11)
O1—S1—C5—C4	−37.5 (4)	C1—C2—C7—C6	−177.3 (6)
O2—S1—C5—C6	15.4 (4)	C3—C2—C7—C6	1.3 (10)
N1—S1—C5—C6	−99.9 (4)	C2—C3—C4—C5	−0.8 (9)
O1—S1—C5—C6	145.9 (3)	C3—C4—C5—C6	1.4 (7)
C24—N2—C26—C31	−62.4 (5)	C3—C4—C5—S1	−175.3 (4)
S2—N2—C26—C31	84.4 (4)	C4—C5—C6—C7	−0.7 (7)
S2—N2—C26—C27	−98.2 (3)	S1—C5—C6—C7	175.9 (4)
S2—N2—C24—C25	152.5 (3)	C5—C6—C7—C2	−0.7 (8)
C26—N2—C24—C25	−61.0 (4)	N1—C10—C11—C12	176.9 (4)
C24—N2—C26—C27	115.0 (4)	C15—C10—C11—C12	−0.3 (6)
C10—N1—C8—C9	55.6 (6)	N1—C10—C15—C14	−178.7 (4)
C8—N1—C10—C15	65.9 (5)	C11—C10—C15—C14	−1.6 (6)
S1—N1—C8—C9	−158.1 (4)	C10—C11—C12—C13	1.4 (6)
C8—N1—C10—C11	−111.4 (4)	C10—C11—C12—C16	−177.7 (4)
S1—N1—C10—C15	−80.4 (4)	C11—C12—C13—C14	−0.6 (6)
S1—N1—C10—C11	102.4 (4)	C16—C12—C13—C14	178.5 (5)
C17—C18—C19—C20	−178.9 (5)	C12—C13—C14—C15	−1.3 (7)
C23—C18—C19—C20	0.8 (7)	C13—C14—C15—C10	2.3 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2	0.93	2.56	2.926 (5)	104
C8—H8A···O1	0.97	2.47	2.927 (7)	109
C11—H11···O1i	0.93	2.48	3.398 (5)	171
C19—H19···O3ii	0.93	2.59	3.480 (5)	161
C22—H22···O3	0.93	2.59	2.946 (5)	103
C24—H24A···O4	0.97	2.50	2.950 (5)	108
C27—H27···O4iii	0.93	2.57	3.503 (5)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1i	0.93	2.48	3.398 (5)	171
C19—H19⋯O3ii	0.93	2.59	3.480 (5)	161
C27—H27⋯O4iii	0.93	2.57	3.503 (5)	176

Symmetry codes: (i) ; (ii) ; (iii) .