4-Chloro-2-methyl-N-(4-methyl-phen-yl)benzene-sulfonamide.

The asymmetric unit of the title compound, C(14)H(14)ClNO(2)S, contains two independent mol-ecules. The torsion angles of the C-SO(2)-NH-C segments in the two mol-ecules are -76.5 (5) and -48.3 (4)°. The two aromatic rings are tilted relative to each other by 76.6 (2)° in one mol-ecule and 70.7 (2)° in the other. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ▶). For our studies of the effect of substituents on the structures of N-(ar­yl)aryl­sulfonamides, see: Gowda et al. (2009 ▶, 2010 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C14H14ClNO2S

M = 295.77

Monoclinic,

a = 10.544 (1) Å

b = 10.674 (1) Å

c = 25.196 (3) Å

β = 96.83 (1)°

V = 2815.6 (5) Å3

Z = 8

Cu Kα radiation

μ = 3.77 mm−1

T = 299 K

0.30 × 0.30 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.398, T max = 0.453

5050 measured reflections

4826 independent reflections

3917 reflections with I > 2σ(I)

R int = 0.086

3 standard reflections every 120 min intensity decay: 2.4%

Refinement

R[F 2 > 2σ(F 2)] = 0.097

wR(F 2) = 0.317

S = 1.43

4826 reflections

347 parameters

H-atom parameters constrained

Δρmax = 1.01 e Å−3

Δρmin = −1.01 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810032320/bt5325sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032320/bt5325Isup2.hkl

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

C14H14ClNO2S	F(000) = 1232
Mr = 295.77	Dx = 1.395 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 10.544 (1) Å	θ = 5.9–19.1°
b = 10.674 (1) Å	µ = 3.77 mm−1
c = 25.196 (3) Å	T = 299 K
β = 96.83 (1)°	Prism, colourless
V = 2815.6 (5) Å3	0.30 × 0.30 × 0.25 mm
Z = 8

Enraf–Nonius CAD-4 diffractometer	3917 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.086
graphite	θmax = 66.9°, θmin = 3.5°
ω/2θ scans	h = −12→12
Absorption correction: ψ scan (North et al., 1968)	k = −12→1
Tmin = 0.398, Tmax = 0.453	l = 0→30
5050 measured reflections	3 standard reflections every 120 min
4826 independent reflections	intensity decay: 2.4%

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)] = 0.097	H-atom parameters constrained
wR(F2) = 0.317	w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3
S = 1.43	(Δ/σ)max = 0.019
4826 reflections	Δρmax = 1.01 e Å−3
347 parameters	Δρmin = −1.01 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0106 (15)

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
C1	0.7092 (4)	0.2838 (5)	0.52199 (18)	0.0526 (11)
C2	0.6915 (4)	0.2131 (5)	0.4758 (2)	0.0597 (12)
H2	0.7045	0.1269	0.4776	0.072*
C3	0.6546 (5)	0.2695 (5)	0.42696 (19)	0.0607 (12)
H3	0.6429	0.2220	0.3958	0.073*
C4	0.6356 (5)	0.3958 (6)	0.4252 (2)	0.0659 (13)
C5	0.6518 (5)	0.4666 (5)	0.4711 (2)	0.0700 (14)
H5	0.6376	0.5525	0.4687	0.084*
C6	0.6879 (4)	0.4148 (5)	0.5198 (2)	0.0602 (12)
C7	1.0129 (4)	0.2164 (4)	0.58974 (17)	0.0538 (11)
C8	1.0262 (4)	0.1581 (7)	0.54233 (19)	0.0756 (17)
H8	0.9540	0.1354	0.5195	0.091*
C9	1.1459 (5)	0.1329 (6)	0.5282 (2)	0.0711 (15)
H9	1.1526	0.0907	0.4963	0.085*
C10	1.2545 (4)	0.1677 (5)	0.5594 (2)	0.0607 (12)
C11	1.2403 (5)	0.2234 (5)	0.6070 (3)	0.0746 (16)
H11	1.3130	0.2441	0.6299	0.090*
C12	1.1218 (5)	0.2505 (5)	0.6226 (2)	0.0621 (12)
H12	1.1156	0.2912	0.6548	0.075*
C13	0.7039 (5)	0.4992 (5)	0.5701 (2)	0.0690 (14)
H13A	0.7856	0.4836	0.5901	0.083*
H13B	0.6375	0.4808	0.5919	0.083*
H13C	0.6984	0.5856	0.5594	0.083*
C14	1.3851 (5)	0.1446 (7)	0.5412 (3)	0.0877 (18)
H14A	1.3786	0.1505	0.5029	0.105*
H14B	1.4145	0.0625	0.5522	0.105*
H14C	1.4444	0.2062	0.5568	0.105*
N1	0.8949 (4)	0.2489 (5)	0.60621 (16)	0.0686 (12)
H1A	0.8981	0.3005	0.6325	0.082*
O1	0.7566 (4)	0.0734 (3)	0.56948 (14)	0.0688 (10)
O2	0.6724 (3)	0.2426 (4)	0.62092 (13)	0.0732 (11)
Cl1	0.59229 (18)	0.46510 (19)	0.36388 (7)	0.0995 (7)
S1	0.75361 (10)	0.20254 (13)	0.58248 (4)	0.0579 (5)
C15	0.1219 (3)	0.6717 (4)	0.20092 (16)	0.0433 (9)
C16	0.0837 (4)	0.6148 (4)	0.15189 (19)	0.0539 (11)
H16	0.0822	0.5278	0.1496	0.065*
C17	0.0488 (5)	0.6840 (5)	0.10744 (19)	0.0623 (12)
H17	0.0223	0.6456	0.0749	0.075*
C18	0.0536 (4)	0.8125 (5)	0.1117 (2)	0.0627 (13)
C19	0.0895 (5)	0.8706 (4)	0.1592 (2)	0.0630 (13)
H19	0.0899	0.9576	0.1608	0.076*
C20	0.1252 (4)	0.8023 (4)	0.20515 (18)	0.0522 (10)
C21	0.4121 (4)	0.6191 (4)	0.24823 (16)	0.0447 (9)
C22	0.4261 (4)	0.5450 (4)	0.20440 (19)	0.0554 (11)
H22	0.3661	0.4835	0.1936	0.066*
C23	0.5307 (5)	0.5634 (4)	0.1766 (2)	0.0591 (12)
H23	0.5398	0.5125	0.1473	0.071*
C24	0.6215 (5)	0.6541 (4)	0.1908 (2)	0.0585 (11)
C25	0.6048 (5)	0.7257 (5)	0.2357 (3)	0.0754 (16)
H25	0.6653	0.7865	0.2470	0.090*
C26	0.5028 (4)	0.7098 (5)	0.2637 (2)	0.0630 (13)
H26	0.4943	0.7599	0.2933	0.076*
C27	0.1653 (5)	0.8727 (4)	0.2580 (2)	0.0624 (13)
H27A	0.2518	0.8514	0.2711	0.075*
H27B	0.1099	0.8492	0.2839	0.075*
H27C	0.1590	0.9614	0.2518	0.075*
C28	0.7328 (6)	0.6763 (6)	0.1611 (3)	0.0906 (19)
H28A	0.7071	0.7275	0.1304	0.109*
H28B	0.7644	0.5976	0.1498	0.109*
H28C	0.7989	0.7182	0.1839	0.109*
N2	0.3102 (3)	0.6066 (4)	0.27950 (14)	0.0513 (9)
H2A	0.3264	0.6176	0.3134	0.062*
O3	0.1584 (3)	0.4483 (3)	0.23600 (13)	0.0591 (9)
O4	0.0901 (3)	0.6035 (3)	0.29782 (12)	0.0591 (9)
Cl2	0.01664 (19)	0.9034 (2)	0.05495 (7)	0.1068 (7)
S2	0.16441 (9)	0.57267 (10)	0.25564 (4)	0.0463 (4)

	U11	U22	U33	U12	U13	U23
C1	0.039 (2)	0.067 (3)	0.051 (2)	−0.0111 (19)	0.0023 (17)	−0.014 (2)
C2	0.050 (2)	0.065 (3)	0.063 (3)	−0.008 (2)	−0.001 (2)	−0.009 (2)
C3	0.056 (3)	0.078 (3)	0.046 (2)	−0.007 (2)	−0.0031 (19)	−0.009 (2)
C4	0.051 (2)	0.087 (4)	0.059 (3)	0.000 (2)	0.006 (2)	0.007 (3)
C5	0.061 (3)	0.061 (3)	0.088 (4)	0.005 (2)	0.007 (3)	0.002 (3)
C6	0.043 (2)	0.076 (3)	0.062 (3)	−0.003 (2)	0.0063 (19)	−0.016 (2)
C7	0.048 (2)	0.065 (3)	0.046 (2)	−0.0028 (19)	−0.0032 (18)	0.0065 (19)
C8	0.041 (2)	0.137 (5)	0.045 (2)	0.005 (3)	−0.0059 (19)	−0.014 (3)
C9	0.048 (2)	0.107 (4)	0.058 (3)	0.006 (3)	0.003 (2)	−0.009 (3)
C10	0.044 (2)	0.055 (3)	0.081 (3)	0.002 (2)	0.001 (2)	0.007 (2)
C11	0.051 (3)	0.068 (3)	0.099 (4)	−0.006 (2)	−0.017 (3)	−0.010 (3)
C12	0.059 (3)	0.058 (3)	0.065 (3)	−0.008 (2)	−0.009 (2)	−0.005 (2)
C13	0.060 (3)	0.069 (3)	0.080 (3)	0.001 (2)	0.017 (2)	−0.030 (3)
C14	0.047 (3)	0.092 (4)	0.124 (5)	0.004 (3)	0.010 (3)	−0.003 (4)
N1	0.047 (2)	0.110 (3)	0.048 (2)	−0.008 (2)	0.0038 (16)	−0.024 (2)
O1	0.076 (2)	0.073 (2)	0.058 (2)	−0.0125 (18)	0.0113 (17)	0.0022 (17)
O2	0.0535 (18)	0.124 (3)	0.0464 (18)	−0.0222 (19)	0.0228 (14)	−0.0159 (18)
Cl1	0.0931 (11)	0.1265 (15)	0.0774 (10)	0.0192 (10)	0.0034 (8)	0.0262 (9)
S1	0.0474 (7)	0.0810 (9)	0.0457 (7)	−0.0131 (5)	0.0077 (5)	−0.0067 (5)
C15	0.0366 (18)	0.048 (2)	0.046 (2)	0.0015 (16)	0.0062 (15)	−0.0090 (17)
C16	0.051 (2)	0.053 (2)	0.058 (3)	−0.0032 (19)	0.0037 (19)	−0.009 (2)
C17	0.062 (3)	0.076 (3)	0.048 (2)	0.009 (2)	0.004 (2)	−0.003 (2)
C18	0.050 (2)	0.083 (3)	0.056 (3)	0.020 (2)	0.010 (2)	0.008 (2)
C19	0.055 (3)	0.051 (3)	0.085 (4)	0.016 (2)	0.016 (2)	0.003 (2)
C20	0.049 (2)	0.048 (2)	0.060 (3)	0.0078 (18)	0.0066 (19)	−0.0085 (19)
C21	0.0405 (19)	0.048 (2)	0.045 (2)	0.0003 (17)	0.0023 (16)	0.0022 (17)
C22	0.056 (3)	0.048 (2)	0.063 (3)	−0.0056 (19)	0.013 (2)	−0.007 (2)
C23	0.066 (3)	0.051 (2)	0.064 (3)	0.004 (2)	0.020 (2)	−0.004 (2)
C24	0.056 (2)	0.053 (2)	0.070 (3)	0.002 (2)	0.023 (2)	0.004 (2)
C25	0.057 (3)	0.070 (3)	0.103 (4)	−0.019 (2)	0.026 (3)	−0.027 (3)
C26	0.052 (2)	0.071 (3)	0.067 (3)	−0.009 (2)	0.013 (2)	−0.023 (3)
C27	0.073 (3)	0.042 (2)	0.070 (3)	0.010 (2)	−0.001 (2)	−0.019 (2)
C28	0.086 (4)	0.082 (4)	0.114 (5)	−0.015 (3)	0.053 (4)	−0.006 (4)
N2	0.0413 (17)	0.070 (2)	0.0421 (18)	−0.0051 (16)	0.0027 (14)	0.0000 (16)
O3	0.065 (2)	0.0463 (17)	0.066 (2)	−0.0074 (14)	0.0089 (15)	0.0000 (14)
O4	0.0509 (17)	0.082 (2)	0.0487 (17)	−0.0144 (15)	0.0230 (13)	−0.0088 (15)
Cl2	0.1074 (13)	0.1270 (15)	0.0883 (12)	0.0445 (11)	0.0214 (10)	0.0449 (10)
S2	0.0427 (6)	0.0495 (6)	0.0469 (7)	−0.0047 (4)	0.0062 (4)	−0.0025 (4)

C1—C2	1.381 (7)	C15—C16	1.392 (6)
C1—C6	1.416 (7)	C15—C20	1.399 (6)
C1—S1	1.768 (5)	C15—S2	1.753 (4)
C2—C3	1.384 (7)	C16—C17	1.356 (7)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.362 (8)	C17—C18	1.377 (8)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.374 (8)	C18—C19	1.360 (7)
C4—Cl1	1.726 (5)	C18—Cl2	1.734 (5)
C5—C6	1.360 (8)	C19—C20	1.381 (7)
C5—H5	0.9300	C19—H19	0.9300
C6—C13	1.547 (6)	C20—C27	1.543 (6)
C7—C8	1.369 (7)	C21—C22	1.381 (6)
C7—C12	1.382 (6)	C21—C26	1.384 (6)
C7—N1	1.401 (6)	C21—N2	1.412 (5)
C8—C9	1.378 (7)	C22—C23	1.389 (7)
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.362 (7)	C23—C24	1.379 (7)
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.363 (8)	C24—C25	1.394 (7)
C10—C14	1.522 (7)	C24—C28	1.484 (7)
C11—C12	1.384 (8)	C25—C26	1.365 (7)
C11—H11	0.9300	C25—H25	0.9300
C12—H12	0.9300	C26—H26	0.9300
C13—H13A	0.9600	C27—H27A	0.9600
C13—H13B	0.9600	C27—H27B	0.9600
C13—H13C	0.9600	C27—H27C	0.9600
C14—H14A	0.9600	C28—H28A	0.9600
C14—H14B	0.9600	C28—H28B	0.9600
C14—H14C	0.9600	C28—H28C	0.9600
N1—S1	1.615 (4)	N2—S2	1.623 (3)
N1—H1A	0.8600	N2—H2A	0.8600
O1—S1	1.418 (4)	O3—S2	1.415 (3)
O2—S1	1.433 (3)	O4—S2	1.432 (3)
C2—C1—C6	120.2 (5)	C16—C15—C20	120.3 (4)
C2—C1—S1	116.9 (4)	C16—C15—S2	117.1 (3)
C6—C1—S1	122.9 (3)	C20—C15—S2	122.7 (3)
C1—C2—C3	120.5 (5)	C17—C16—C15	121.1 (4)
C1—C2—H2	119.8	C17—C16—H16	119.4
C3—C2—H2	119.8	C15—C16—H16	119.4
C4—C3—C2	118.9 (5)	C16—C17—C18	118.3 (5)
C4—C3—H3	120.5	C16—C17—H17	120.8
C2—C3—H3	120.5	C18—C17—H17	120.8
C3—C4—C5	120.9 (5)	C19—C18—C17	121.8 (5)
C3—C4—Cl1	118.4 (4)	C19—C18—Cl2	118.9 (4)
C5—C4—Cl1	120.7 (5)	C17—C18—Cl2	119.3 (4)
C6—C5—C4	121.9 (5)	C18—C19—C20	121.1 (5)
C6—C5—H5	119.0	C18—C19—H19	119.5
C4—C5—H5	119.0	C20—C19—H19	119.5
C5—C6—C1	117.6 (5)	C19—C20—C15	117.4 (4)
C5—C6—C13	119.6 (5)	C19—C20—C27	119.0 (4)
C1—C6—C13	122.8 (5)	C15—C20—C27	123.6 (4)
C8—C7—C12	118.6 (5)	C22—C21—C26	119.4 (4)
C8—C7—N1	123.9 (4)	C22—C21—N2	123.6 (4)
C12—C7—N1	117.5 (4)	C26—C21—N2	117.1 (4)
C7—C8—C9	120.5 (4)	C21—C22—C23	119.3 (4)
C7—C8—H8	119.8	C21—C22—H22	120.3
C9—C8—H8	119.8	C23—C22—H22	120.3
C10—C9—C8	122.0 (5)	C24—C23—C22	122.4 (4)
C10—C9—H9	119.0	C24—C23—H23	118.8
C8—C9—H9	119.0	C22—C23—H23	118.8
C9—C10—C11	117.0 (5)	C23—C24—C25	116.4 (4)
C9—C10—C14	120.7 (5)	C23—C24—C28	123.2 (5)
C11—C10—C14	122.3 (5)	C25—C24—C28	120.4 (5)
C10—C11—C12	122.6 (5)	C26—C25—C24	122.3 (5)
C10—C11—H11	118.7	C26—C25—H25	118.8
C12—C11—H11	118.7	C24—C25—H25	118.8
C11—C12—C7	119.2 (5)	C25—C26—C21	120.1 (5)
C11—C12—H12	120.4	C25—C26—H26	119.9
C7—C12—H12	120.4	C21—C26—H26	119.9
C6—C13—H13A	109.5	C20—C27—H27A	109.5
C6—C13—H13B	109.5	C20—C27—H27B	109.5
H13A—C13—H13B	109.5	H27A—C27—H27B	109.5
C6—C13—H13C	109.5	C20—C27—H27C	109.5
H13A—C13—H13C	109.5	H27A—C27—H27C	109.5
H13B—C13—H13C	109.5	H27B—C27—H27C	109.5
C10—C14—H14A	109.5	C24—C28—H28A	109.5
C10—C14—H14B	109.5	C24—C28—H28B	109.5
H14A—C14—H14B	109.5	H28A—C28—H28B	109.5
C10—C14—H14C	109.5	C24—C28—H28C	109.5
H14A—C14—H14C	109.5	H28A—C28—H28C	109.5
H14B—C14—H14C	109.5	H28B—C28—H28C	109.5
C7—N1—S1	128.8 (3)	C21—N2—S2	124.3 (3)
C7—N1—H1A	115.6	C21—N2—H2A	117.8
S1—N1—H1A	115.6	S2—N2—H2A	117.8
O1—S1—O2	118.6 (2)	O3—S2—O4	118.0 (2)
O1—S1—N1	109.8 (2)	O3—S2—N2	109.8 (2)
O2—S1—N1	104.9 (2)	O4—S2—N2	104.56 (19)
O1—S1—C1	106.8 (2)	O3—S2—C15	107.08 (19)
O2—S1—C1	108.5 (2)	O4—S2—C15	109.5 (2)
N1—S1—C1	107.9 (2)	N2—S2—C15	107.42 (19)
C6—C1—C2—C3	0.9 (7)	C20—C15—C16—C17	−0.2 (7)
S1—C1—C2—C3	178.9 (4)	S2—C15—C16—C17	179.8 (4)
C1—C2—C3—C4	−0.2 (7)	C15—C16—C17—C18	0.9 (7)
C2—C3—C4—C5	−0.5 (8)	C16—C17—C18—C19	−1.4 (8)
C2—C3—C4—Cl1	178.9 (4)	C16—C17—C18—Cl2	177.0 (4)
C3—C4—C5—C6	0.5 (8)	C17—C18—C19—C20	1.3 (8)
Cl1—C4—C5—C6	−178.9 (4)	Cl2—C18—C19—C20	−177.2 (4)
C4—C5—C6—C1	0.2 (8)	C18—C19—C20—C15	−0.5 (7)
C4—C5—C6—C13	−179.7 (5)	C18—C19—C20—C27	179.9 (4)
C2—C1—C6—C5	−0.9 (7)	C16—C15—C20—C19	0.0 (6)
S1—C1—C6—C5	−178.8 (4)	S2—C15—C20—C19	180.0 (3)
C2—C1—C6—C13	179.0 (4)	C16—C15—C20—C27	179.6 (4)
S1—C1—C6—C13	1.1 (6)	S2—C15—C20—C27	−0.5 (6)
C12—C7—C8—C9	0.8 (9)	C26—C21—C22—C23	−0.3 (7)
N1—C7—C8—C9	177.9 (6)	N2—C21—C22—C23	−179.1 (4)
C7—C8—C9—C10	−2.1 (10)	C21—C22—C23—C24	−0.6 (7)
C8—C9—C10—C11	3.3 (9)	C22—C23—C24—C25	1.4 (8)
C8—C9—C10—C14	−176.7 (6)	C22—C23—C24—C28	−179.1 (5)
C9—C10—C11—C12	−3.4 (8)	C23—C24—C25—C26	−1.5 (9)
C14—C10—C11—C12	176.6 (5)	C28—C24—C25—C26	179.0 (6)
C10—C11—C12—C7	2.2 (9)	C24—C25—C26—C21	0.7 (9)
C8—C7—C12—C11	−0.8 (8)	C22—C21—C26—C25	0.3 (8)
N1—C7—C12—C11	−178.1 (5)	N2—C21—C26—C25	179.1 (5)
C8—C7—N1—S1	14.5 (8)	C22—C21—N2—S2	−37.0 (6)
C12—C7—N1—S1	−168.4 (4)	C26—C21—N2—S2	144.2 (4)
C7—N1—S1—O1	39.5 (5)	C21—N2—S2—O3	67.9 (4)
C7—N1—S1—O2	167.9 (5)	C21—N2—S2—O4	−164.5 (4)
C7—N1—S1—C1	−76.5 (5)	C21—N2—S2—C15	−48.3 (4)
C2—C1—S1—O1	−2.3 (4)	C16—C15—S2—O3	4.1 (4)
C6—C1—S1—O1	175.6 (4)	C20—C15—S2—O3	−175.9 (3)
C2—C1—S1—O2	−131.2 (4)	C16—C15—S2—O4	−125.0 (3)
C6—C1—S1—O2	46.7 (4)	C20—C15—S2—O4	55.0 (4)
C2—C1—S1—N1	115.6 (4)	C16—C15—S2—N2	122.0 (3)
C6—C1—S1—N1	−66.5 (4)	C20—C15—S2—N2	−58.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4i	0.86	2.02	2.874 (5)	171.
N2—H2A···O2i	0.86	2.23	2.968 (5)	144.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4i	0.86	2.02	2.874 (5)	171
N2—H2A⋯O2i	0.86	2.23	2.968 (5)	144

Symmetry code: (i) .