N-(4-Methyl-benzo-yl)-2-nitro-benzene-sulfonamide.

The asymmetric unit of the title compound, C(14)H(12)N(2)O(5)S, contains two independent mol-ecules. The dihedral angles between the aromatic rings are 82.03 (9) and 79.47 (8)° in the two independent mol-ecules. In the crystal, the two mol-ecules in the asymmetric unit are linked into dimers via pairs of N-H⋯O(S) hydrogen bonds to generate C(4) chains.

Related literature

For studies, including ours, on the effects of substituents on the structures and other aspects of N-(ar­yl)amides, see: Bowes et al. (2003 ▶); Gowda et al. (1999 ▶, 2003 ▶). For N-(ar­yl)methane­sulfonamides, see: Gowda et al. (2007 ▶). For N-(ar­yl)aryl­sulfonamides, see: Shetty & Gowda (2005 ▶). For N-(sub­stituted benzo­yl)aryl­sulfonamides, see: Suchetan et al. (2012 ▶). For N-chloro­aryl­amides, see: Jyothi & Gowda (2004 ▶). For N-bromo­aryl­sulfonamides, see: Usha & Gowda (2006 ▶).

Experimental

Crystal data

C14H12N2O5S

M = 320.32

Triclinic,

a = 10.860 (1) Å

b = 11.716 (2) Å

c = 12.841 (2) Å

α = 114.51 (2)°

β = 102.99 (2)°

γ = 91.16 (1)°

V = 1436.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.44 × 0.44 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.898, T max = 0.942

8993 measured reflections

5772 independent reflections

4069 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.116

S = 1.06

5772 reflections

405 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data n class="Disease">reduction: CrysAlis RED; 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 datablock(s) I, global. DOI: 10.1107/S1600536812003522/bt5801sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003522/bt5801Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812003522/bt5801Isup3.cml

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

C14H12N2O5S	Z = 4
Mr = 320.32	F(000) = 664
Triclinic, P1	Dx = 1.481 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.860 (1) Å	Cell parameters from 3497 reflections
b = 11.716 (2) Å	θ = 2.6–27.7°
c = 12.841 (2) Å	µ = 0.25 mm−1
α = 114.51 (2)°	T = 293 K
β = 102.99 (2)°	Prism, colourless
γ = 91.16 (1)°	0.44 × 0.44 × 0.24 mm
V = 1436.6 (4) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	5772 independent reflections
Radiation source: fine-focus sealed tube	4069 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→13
Tmin = 0.898, Tmax = 0.942	k = −12→14
8993 measured reflections	l = −14→16

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0321P)2 + 1.1761P] where P = (Fo2 + 2Fc2)/3
5772 reflections	(Δ/σ)max = 0.018
405 parameters	Δρmax = 0.29 e Å−3
2 restraints	Δρmin = −0.31 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	−0.0965 (2)	0.5718 (2)	0.3025 (2)	0.0424 (6)
C2	−0.1921 (3)	0.5564 (2)	0.2042 (3)	0.0485 (6)
C3	−0.3051 (3)	0.6057 (3)	0.2163 (3)	0.0642 (9)
H3	−0.3696	0.5933	0.1498	0.077*
C4	−0.3212 (3)	0.6736 (3)	0.3285 (4)	0.0713 (10)
H4	−0.3959	0.7095	0.3375	0.086*
C5	−0.2284 (3)	0.6885 (3)	0.4263 (3)	0.0661 (9)
H5	−0.2405	0.7333	0.5015	0.079*
C6	−0.1166 (3)	0.6369 (3)	0.4134 (3)	0.0505 (7)
H6	−0.0541	0.6462	0.4802	0.061*
C7	0.1874 (2)	0.7296 (3)	0.3702 (2)	0.0467 (6)
C8	0.2763 (2)	0.8070 (2)	0.3448 (2)	0.0428 (6)
C9	0.2955 (3)	0.9366 (3)	0.4126 (3)	0.0587 (8)
H9	0.2529	0.9730	0.4714	0.070*
C10	0.3781 (3)	1.0120 (3)	0.3926 (3)	0.0659 (9)
H10	0.3898	1.0990	0.4384	0.079*
C11	0.4436 (3)	0.9617 (3)	0.3068 (3)	0.0545 (7)
C12	0.4233 (3)	0.8330 (3)	0.2396 (3)	0.0525 (7)
H12	0.4656	0.7971	0.1805	0.063*
C13	0.3409 (3)	0.7557 (3)	0.2582 (2)	0.0473 (6)
H13	0.3292	0.6688	0.2121	0.057*
C14	0.5351 (3)	1.0447 (3)	0.2876 (3)	0.0790 (10)
H14A	0.6115	1.0720	0.3509	0.095*
H14B	0.4966	1.1172	0.2861	0.095*
H14C	0.5556	0.9979	0.2136	0.095*
N1	0.1440 (2)	0.6072 (2)	0.2821 (2)	0.0488 (5)
H1N	0.157 (3)	0.583 (3)	0.2132 (13)	0.059*
N2	−0.1779 (3)	0.4904 (3)	0.0836 (3)	0.0704 (8)
O1	0.09629 (18)	0.4991 (2)	0.40379 (19)	0.0633 (6)
O2	0.02871 (19)	0.39485 (17)	0.18596 (19)	0.0601 (5)
O3	0.1506 (2)	0.7687 (2)	0.45992 (18)	0.0659 (6)
O4	−0.0976 (3)	0.5353 (3)	0.0563 (2)	0.0944 (8)
O5	−0.2522 (4)	0.3971 (3)	0.0170 (2)	0.1311 (13)
S1	0.04803 (6)	0.50626 (6)	0.29466 (7)	0.04812 (18)
C15	0.4933 (2)	0.2942 (2)	0.1683 (2)	0.0380 (5)
C16	0.5306 (2)	0.3732 (2)	0.2893 (2)	0.0414 (6)
C17	0.6504 (2)	0.3816 (3)	0.3571 (2)	0.0468 (6)
H17	0.6740	0.4362	0.4374	0.056*
C18	0.7355 (3)	0.3071 (3)	0.3037 (3)	0.0503 (7)
H18	0.8171	0.3115	0.3485	0.060*
C19	0.7009 (3)	0.2267 (3)	0.1852 (3)	0.0507 (7)
H19	0.7585	0.1757	0.1506	0.061*
C20	0.5805 (3)	0.2213 (2)	0.1172 (2)	0.0477 (6)
H20	0.5583	0.1683	0.0365	0.057*
C21	0.2377 (3)	0.0971 (2)	0.0854 (2)	0.0479 (6)
C22	0.1465 (2)	0.0519 (2)	0.1349 (2)	0.0457 (6)
C23	0.1197 (3)	−0.0777 (3)	0.0968 (3)	0.0570 (7)
H23	0.1556	−0.1334	0.0392	0.068*
C24	0.0401 (3)	−0.1238 (3)	0.1443 (3)	0.0623 (8)
H24	0.0222	−0.2108	0.1168	0.075*
C25	−0.0139 (3)	−0.0445 (3)	0.2314 (3)	0.0572 (7)
C26	0.0137 (3)	0.0836 (3)	0.2686 (3)	0.0613 (8)
H26	−0.0217	0.1391	0.3268	0.074*
C27	0.0925 (3)	0.1320 (3)	0.2217 (3)	0.0560 (7)
H27	0.1093	0.2191	0.2487	0.067*
C28	−0.0969 (3)	−0.0950 (3)	0.2860 (4)	0.0813 (10)
H28A	−0.0514	−0.1478	0.3175	0.098*
H28B	−0.1728	−0.1437	0.2267	0.098*
H28C	−0.1197	−0.0257	0.3486	0.098*
N3	0.2353 (2)	0.2211 (2)	0.0981 (2)	0.0467 (5)
H3N	0.185 (2)	0.269 (2)	0.133 (2)	0.056*
N4	0.4405 (2)	0.4484 (2)	0.3514 (2)	0.0524 (6)
O6	0.3190 (2)	0.42572 (18)	0.11978 (19)	0.0637 (6)
O7	0.3564 (2)	0.2349 (2)	−0.04299 (17)	0.0708 (6)
O8	0.3129 (2)	0.03374 (18)	0.0378 (2)	0.0677 (6)
O9	0.3422 (2)	0.3918 (2)	0.34577 (19)	0.0780 (7)
O10	0.4714 (2)	0.5617 (2)	0.4097 (2)	0.0713 (6)
S2	0.34704 (7)	0.29805 (7)	0.07566 (6)	0.04910 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0391 (14)	0.0388 (13)	0.0565 (16)	0.0053 (11)	0.0140 (12)	0.0266 (12)
C2	0.0499 (16)	0.0463 (15)	0.0566 (17)	0.0015 (12)	0.0095 (13)	0.0316 (14)
C3	0.0475 (17)	0.076 (2)	0.083 (2)	0.0057 (15)	0.0037 (16)	0.055 (2)
C4	0.0478 (18)	0.091 (2)	0.103 (3)	0.0269 (17)	0.0312 (19)	0.062 (2)
C5	0.060 (2)	0.075 (2)	0.078 (2)	0.0204 (17)	0.0329 (18)	0.0380 (19)
C6	0.0441 (15)	0.0573 (17)	0.0577 (18)	0.0087 (13)	0.0150 (13)	0.0309 (14)
C7	0.0390 (14)	0.0520 (16)	0.0475 (16)	0.0079 (12)	0.0113 (12)	0.0198 (13)
C8	0.0377 (13)	0.0456 (15)	0.0452 (15)	0.0063 (11)	0.0072 (11)	0.0214 (12)
C9	0.0572 (18)	0.0503 (17)	0.0599 (19)	0.0060 (14)	0.0195 (15)	0.0132 (14)
C10	0.068 (2)	0.0407 (16)	0.081 (2)	0.0025 (15)	0.0139 (18)	0.0211 (16)
C11	0.0503 (16)	0.0547 (17)	0.0661 (19)	0.0029 (13)	0.0075 (14)	0.0373 (15)
C12	0.0562 (17)	0.0580 (17)	0.0555 (17)	0.0113 (14)	0.0205 (14)	0.0329 (15)
C13	0.0536 (16)	0.0420 (14)	0.0487 (16)	0.0073 (12)	0.0136 (13)	0.0216 (12)
C14	0.079 (2)	0.073 (2)	0.100 (3)	−0.0053 (19)	0.018 (2)	0.054 (2)
N1	0.0477 (13)	0.0477 (13)	0.0526 (14)	0.0023 (10)	0.0190 (11)	0.0202 (12)
N2	0.084 (2)	0.0717 (19)	0.0577 (18)	0.0124 (16)	0.0071 (16)	0.0360 (16)
O1	0.0498 (12)	0.0827 (15)	0.0815 (15)	0.0207 (11)	0.0173 (11)	0.0576 (13)
O2	0.0604 (13)	0.0395 (10)	0.0803 (15)	0.0126 (9)	0.0240 (11)	0.0224 (10)
O3	0.0666 (14)	0.0700 (14)	0.0563 (13)	−0.0036 (11)	0.0273 (11)	0.0171 (11)
O4	0.0899 (19)	0.132 (2)	0.0839 (19)	0.0306 (18)	0.0437 (16)	0.0570 (18)
O5	0.191 (4)	0.098 (2)	0.0616 (18)	−0.042 (2)	−0.013 (2)	0.0194 (16)
S1	0.0431 (4)	0.0460 (4)	0.0649 (5)	0.0112 (3)	0.0174 (3)	0.0311 (3)
C15	0.0444 (14)	0.0359 (13)	0.0373 (13)	0.0020 (11)	0.0130 (11)	0.0180 (11)
C16	0.0447 (14)	0.0406 (14)	0.0440 (15)	0.0077 (11)	0.0192 (12)	0.0189 (12)
C17	0.0442 (15)	0.0498 (15)	0.0416 (15)	0.0018 (12)	0.0118 (12)	0.0150 (12)
C18	0.0403 (15)	0.0529 (16)	0.0591 (18)	0.0062 (12)	0.0140 (13)	0.0249 (14)
C19	0.0490 (16)	0.0483 (15)	0.0584 (18)	0.0124 (13)	0.0251 (14)	0.0205 (14)
C20	0.0583 (17)	0.0423 (14)	0.0434 (15)	0.0048 (12)	0.0208 (13)	0.0153 (12)
C21	0.0466 (15)	0.0353 (14)	0.0478 (16)	0.0053 (12)	0.0049 (12)	0.0081 (12)
C22	0.0418 (14)	0.0371 (13)	0.0495 (15)	0.0060 (11)	0.0019 (12)	0.0152 (12)
C23	0.0618 (18)	0.0384 (15)	0.0591 (18)	0.0053 (13)	0.0095 (15)	0.0128 (13)
C24	0.068 (2)	0.0386 (15)	0.071 (2)	−0.0025 (14)	0.0025 (17)	0.0222 (15)
C25	0.0461 (16)	0.0550 (17)	0.069 (2)	0.0004 (13)	0.0009 (14)	0.0326 (16)
C26	0.0589 (18)	0.0525 (17)	0.076 (2)	0.0148 (14)	0.0243 (16)	0.0271 (16)
C27	0.0614 (18)	0.0370 (14)	0.071 (2)	0.0116 (13)	0.0217 (16)	0.0219 (14)
C28	0.072 (2)	0.077 (2)	0.099 (3)	−0.0049 (19)	0.017 (2)	0.046 (2)
N3	0.0446 (13)	0.0407 (12)	0.0497 (14)	0.0066 (10)	0.0092 (10)	0.0160 (11)
N4	0.0483 (14)	0.0625 (16)	0.0407 (13)	0.0112 (12)	0.0136 (11)	0.0155 (12)
O6	0.0703 (14)	0.0520 (12)	0.0798 (15)	0.0140 (10)	0.0135 (11)	0.0415 (11)
O7	0.0799 (15)	0.0911 (16)	0.0404 (11)	0.0088 (13)	0.0109 (10)	0.0296 (11)
O8	0.0688 (14)	0.0444 (11)	0.0808 (15)	0.0134 (10)	0.0312 (12)	0.0119 (10)
O9	0.0462 (12)	0.0970 (18)	0.0665 (15)	−0.0018 (12)	0.0232 (11)	0.0081 (13)
O10	0.0874 (16)	0.0527 (13)	0.0704 (15)	0.0213 (12)	0.0374 (13)	0.0138 (11)
S2	0.0561 (4)	0.0505 (4)	0.0443 (4)	0.0073 (3)	0.0089 (3)	0.0258 (3)

C1—C6	1.379 (4)	C15—C20	1.381 (3)
C1—C2	1.385 (4)	C15—C16	1.394 (3)
C1—S1	1.766 (3)	C15—S2	1.771 (3)
C2—C3	1.380 (4)	C16—C17	1.370 (4)
C2—N2	1.462 (4)	C16—N4	1.474 (3)
C3—C4	1.380 (5)	C17—C18	1.381 (4)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.366 (5)	C18—C19	1.372 (4)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.379 (4)	C19—C20	1.383 (4)
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C7—O3	1.214 (3)	C21—O8	1.210 (3)
C7—N1	1.395 (3)	C21—N3	1.395 (3)
C7—C8	1.487 (4)	C21—C22	1.486 (4)
C8—C13	1.380 (4)	C22—C27	1.384 (4)
C8—C9	1.384 (4)	C22—C23	1.389 (4)
C9—C10	1.381 (4)	C23—C24	1.379 (4)
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.378 (4)	C24—C25	1.384 (4)
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.374 (4)	C25—C26	1.376 (4)
C11—C14	1.505 (4)	C25—C28	1.503 (4)
C12—C13	1.386 (4)	C26—C27	1.382 (4)
C12—H12	0.9300	C26—H26	0.9300
C13—H13	0.9300	C27—H27	0.9300
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	1.641 (2)	N3—S2	1.642 (2)
N1—H1N	0.855 (10)	N3—H3N	0.853 (10)
N2—O4	1.196 (4)	N4—O10	1.216 (3)
N2—O5	1.207 (4)	N4—O9	1.216 (3)
O1—S1	1.419 (2)	O6—S2	1.430 (2)
O2—S1	1.429 (2)	O7—S2	1.420 (2)
C6—C1—C2	118.7 (2)	C20—C15—C16	118.1 (2)
C6—C1—S1	117.4 (2)	C20—C15—S2	118.89 (19)
C2—C1—S1	123.8 (2)	C16—C15—S2	122.58 (19)
C3—C2—C1	120.9 (3)	C17—C16—C15	122.1 (2)
C3—C2—N2	116.8 (3)	C17—C16—N4	116.7 (2)
C1—C2—N2	122.3 (3)	C15—C16—N4	121.2 (2)
C2—C3—C4	119.1 (3)	C16—C17—C18	118.6 (2)
C2—C3—H3	120.4	C16—C17—H17	120.7
C4—C3—H3	120.4	C18—C17—H17	120.7
C5—C4—C3	120.6 (3)	C19—C18—C17	120.8 (3)
C5—C4—H4	119.7	C19—C18—H18	119.6
C3—C4—H4	119.7	C17—C18—H18	119.6
C4—C5—C6	119.9 (3)	C18—C19—C20	120.1 (3)
C4—C5—H5	120.0	C18—C19—H19	120.0
C6—C5—H5	120.0	C20—C19—H19	120.0
C1—C6—C5	120.6 (3)	C15—C20—C19	120.4 (2)
C1—C6—H6	119.7	C15—C20—H20	119.8
C5—C6—H6	119.7	C19—C20—H20	119.8
O3—C7—N1	120.4 (2)	O8—C21—N3	119.8 (3)
O3—C7—C8	123.6 (3)	O8—C21—C22	123.9 (2)
N1—C7—C8	116.0 (2)	N3—C21—C22	116.3 (2)
C13—C8—C9	118.8 (3)	C27—C22—C23	118.3 (3)
C13—C8—C7	123.2 (2)	C27—C22—C21	123.5 (2)
C9—C8—C7	118.0 (2)	C23—C22—C21	118.1 (3)
C10—C9—C8	119.9 (3)	C24—C23—C22	120.2 (3)
C10—C9—H9	120.0	C24—C23—H23	119.9
C8—C9—H9	120.0	C22—C23—H23	119.9
C11—C10—C9	121.8 (3)	C23—C24—C25	122.0 (3)
C11—C10—H10	119.1	C23—C24—H24	119.0
C9—C10—H10	119.1	C25—C24—H24	119.0
C12—C11—C10	117.8 (3)	C26—C25—C24	117.3 (3)
C12—C11—C14	121.0 (3)	C26—C25—C28	120.9 (3)
C10—C11—C14	121.2 (3)	C24—C25—C28	121.8 (3)
C11—C12—C13	121.3 (3)	C25—C26—C27	121.8 (3)
C11—C12—H12	119.3	C25—C26—H26	119.1
C13—C12—H12	119.3	C27—C26—H26	119.1
C8—C13—C12	120.4 (3)	C26—C27—C22	120.5 (3)
C8—C13—H13	119.8	C26—C27—H27	119.7
C12—C13—H13	119.8	C22—C27—H27	119.7
C11—C14—H14A	109.5	C25—C28—H28A	109.5
C11—C14—H14B	109.5	C25—C28—H28B	109.5
H14A—C14—H14B	109.5	H28A—C28—H28B	109.5
C11—C14—H14C	109.5	C25—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	123.28 (19)	C21—N3—S2	123.47 (19)
C7—N1—H1N	121 (2)	C21—N3—H3N	122 (2)
S1—N1—H1N	115 (2)	S2—N3—H3N	113.1 (19)
O4—N2—O5	124.6 (3)	O10—N4—O9	124.0 (2)
O4—N2—C2	118.1 (3)	O10—N4—C16	118.3 (2)
O5—N2—C2	117.2 (3)	O9—N4—C16	117.5 (2)
O1—S1—O2	119.62 (13)	O7—S2—O6	119.71 (14)
O1—S1—N1	109.89 (13)	O7—S2—N3	110.46 (13)
O2—S1—N1	104.51 (12)	O6—S2—N3	104.21 (12)
O1—S1—C1	106.60 (13)	O7—S2—C15	107.13 (13)
O2—S1—C1	109.45 (13)	O6—S2—C15	107.80 (12)
N1—S1—C1	106.06 (12)	N3—S2—C15	106.88 (11)
C6—C1—C2—C3	0.4 (4)	C20—C15—C16—C17	1.0 (4)
S1—C1—C2—C3	177.3 (2)	S2—C15—C16—C17	−171.2 (2)
C6—C1—C2—N2	179.0 (3)	C20—C15—C16—N4	−176.5 (2)
S1—C1—C2—N2	−4.1 (4)	S2—C15—C16—N4	11.3 (3)
C1—C2—C3—C4	1.5 (4)	C15—C16—C17—C18	−1.3 (4)
N2—C2—C3—C4	−177.2 (3)	N4—C16—C17—C18	176.3 (2)
C2—C3—C4—C5	−2.1 (5)	C16—C17—C18—C19	0.1 (4)
C3—C4—C5—C6	0.9 (5)	C17—C18—C19—C20	1.3 (4)
C2—C1—C6—C5	−1.6 (4)	C16—C15—C20—C19	0.5 (4)
S1—C1—C6—C5	−178.7 (2)	S2—C15—C20—C19	173.0 (2)
C4—C5—C6—C1	0.9 (5)	C18—C19—C20—C15	−1.7 (4)
O3—C7—C8—C13	164.3 (3)	O8—C21—C22—C27	157.4 (3)
N1—C7—C8—C13	−17.4 (4)	N3—C21—C22—C27	−21.4 (4)
O3—C7—C8—C9	−15.1 (4)	O8—C21—C22—C23	−18.9 (4)
N1—C7—C8—C9	163.2 (3)	N3—C21—C22—C23	162.3 (2)
C13—C8—C9—C10	0.1 (4)	C27—C22—C23—C24	0.7 (4)
C7—C8—C9—C10	179.5 (3)	C21—C22—C23—C24	177.1 (3)
C8—C9—C10—C11	−0.4 (5)	C22—C23—C24—C25	−1.0 (5)
C9—C10—C11—C12	0.7 (5)	C23—C24—C25—C26	0.8 (5)
C9—C10—C11—C14	−178.8 (3)	C23—C24—C25—C28	−177.8 (3)
C10—C11—C12—C13	−0.8 (4)	C24—C25—C26—C27	−0.3 (5)
C14—C11—C12—C13	178.8 (3)	C28—C25—C26—C27	178.3 (3)
C9—C8—C13—C12	−0.1 (4)	C25—C26—C27—C22	0.0 (5)
C7—C8—C13—C12	−179.5 (2)	C23—C22—C27—C26	−0.2 (4)
C11—C12—C13—C8	0.5 (4)	C21—C22—C27—C26	−176.4 (3)
O3—C7—N1—S1	−3.1 (4)	O8—C21—N3—S2	−12.4 (4)
C8—C7—N1—S1	178.58 (18)	C22—C21—N3—S2	166.47 (19)
C3—C2—N2—O4	114.8 (3)	C17—C16—N4—O10	55.5 (3)
C1—C2—N2—O4	−63.9 (4)	C15—C16—N4—O10	−126.9 (3)
C3—C2—N2—O5	−62.0 (4)	C17—C16—N4—O9	−120.9 (3)
C1—C2—N2—O5	119.3 (3)	C15—C16—N4—O9	56.8 (3)
C7—N1—S1—O1	−50.4 (3)	C21—N3—S2—O7	60.8 (3)
C7—N1—S1—O2	−180.0 (2)	C21—N3—S2—O6	−169.4 (2)
C7—N1—S1—C1	64.4 (2)	C21—N3—S2—C15	−55.4 (2)
C6—C1—S1—O1	19.2 (2)	C20—C15—S2—O7	−8.7 (2)
C2—C1—S1—O1	−157.8 (2)	C16—C15—S2—O7	163.4 (2)
C6—C1—S1—O2	149.9 (2)	C20—C15—S2—O6	−138.8 (2)
C2—C1—S1—O2	−27.1 (3)	C16—C15—S2—O6	33.3 (2)
C6—C1—S1—N1	−97.9 (2)	C20—C15—S2—N3	109.7 (2)
C2—C1—S1—N1	85.1 (2)	C16—C15—S2—N3	−78.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O2	0.85 (1)	2.30 (1)	3.141 (3)	168 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O2	0.85 (1)	2.30 (1)	3.141 (3)	168 (3)