N-(2,3-Dimethyl-phen-yl)-2-nitro-benzene-sulfonamide.

There are two independent mol-ecules in the asymmetric unit of the title compound, C(14)H(14)N(2)O(4)S. The N-H bonds are syn to the ortho-nitro groups in the sulfonyl benzene rings and anti to the methyl groups in the aniline benzene rings. The mol-ecules are twisted at the S-N bonds with torsion angles of -60.4 (3) and 58.8 (3)° in the two mol-ecules. The dihedral angles between the planes of the sulfonyl and the anilino benzene rings are 53.67 (8) and 56.99 (9)°. The amide H atoms of both mol-ecules are involved in an intra-molecular hydrogen bond, generating an S(7) motif. In the crystal, pairs of N-H⋯O(S) hydrogen bonds link like mol-ecules into inversion dimers.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Alkan et al. (2011 ▶); Bowes et al. (2003 ▶); Gowda et al. (1994 ▶); Saeed et al. (2010 ▶); Shahwar et al. (2012 ▶), of N-aryl­sulfonamides, see: Chaithanya et al. (2012 ▶); Gowda et al. (2002 ▶) and of N-chloro­aryl­sulfonamides, see: Gowda & Shetty (2004 ▶); Shetty & Gowda (2004 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H14N2O4S

M = 306.33

Triclinic,

a = 8.0248 (9) Å

b = 12.633 (1) Å

c = 14.711 (1) Å

α = 88.205 (9)°

β = 80.818 (9)°

γ = 82.323 (9)°

V = 1459.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 293 K

0.44 × 0.40 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.902, T max = 0.945

10389 measured reflections

5936 independent reflections

3935 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.164

S = 1.02

5936 reflections

389 parameters

18 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.73 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812042845/sj5271sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042845/sj5271Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042845/sj5271Isup3.cml

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

C14H14N2O4S	Z = 4
Mr = 306.33	F(000) = 640
Triclinic, P1	Dx = 1.395 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0248 (9) Å	Cell parameters from 2511 reflections
b = 12.633 (1) Å	θ = 2.6–27.8°
c = 14.711 (1) Å	µ = 0.24 mm−1
α = 88.205 (9)°	T = 293 K
β = 80.818 (9)°	Prism, light pink
γ = 82.323 (9)°	0.44 × 0.40 × 0.24 mm
V = 1459.0 (2) Å3

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	5936 independent reflections
Radiation source: fine-focus sealed tube	3935 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Rotation method data acquisition using ω scans.	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −6→10
Tmin = 0.902, Tmax = 0.945	k = −15→15
10389 measured reflections	l = −18→18

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0599P)2 + 1.4896P] where P = (Fo2 + 2Fc2)/3
5936 reflections	(Δ/σ)max = 0.007
389 parameters	Δρmax = 0.73 e Å−3
18 restraints	Δρmin = −0.32 e Å−3

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
S1	0.59078 (10)	0.35977 (6)	0.38703 (6)	0.0426 (2)
O5	0.5488 (3)	0.47186 (18)	0.37132 (17)	0.0537 (6)
O6	0.5067 (3)	0.2854 (2)	0.34621 (17)	0.0561 (6)
O7	0.8170 (3)	0.4954 (2)	0.47995 (19)	0.0637 (7)
O8	0.9658 (5)	0.5631 (2)	0.3634 (2)	0.0896 (10)
N1	0.5588 (4)	0.3406 (2)	0.49664 (19)	0.0454 (7)
H1N	0.581 (5)	0.391 (2)	0.526 (2)	0.055*
N2	0.9020 (4)	0.4890 (2)	0.4036 (2)	0.0523 (7)
C1	0.8118 (4)	0.3235 (2)	0.3470 (2)	0.0372 (7)
C2	0.9393 (4)	0.3844 (2)	0.3586 (2)	0.0399 (7)
C3	1.1079 (4)	0.3496 (3)	0.3287 (2)	0.0488 (8)
H3	1.1912	0.3911	0.3378	0.059*
C4	1.1527 (4)	0.2528 (3)	0.2851 (3)	0.0533 (9)
H4	1.2668	0.2281	0.2654	0.064*
C5	1.0292 (4)	0.1927 (3)	0.2706 (2)	0.0503 (9)
H5	1.0599	0.1279	0.2402	0.060*
C6	0.8602 (4)	0.2276 (3)	0.3009 (2)	0.0437 (8)
H6	0.7776	0.1864	0.2904	0.052*
C7	0.5971 (5)	0.2352 (3)	0.5374 (2)	0.0476 (8)
C8	0.4693 (5)	0.1718 (3)	0.5629 (2)	0.0523 (9)
C9	0.5109 (6)	0.0721 (3)	0.6048 (2)	0.0582 (10)
C10	0.6782 (7)	0.0421 (3)	0.6172 (3)	0.0748 (13)
H10	0.7065	−0.0243	0.6438	0.090*
C11	0.8033 (6)	0.1053 (4)	0.5925 (3)	0.0781 (13)
H11	0.9138	0.0822	0.6028	0.094*
C12	0.7653 (5)	0.2033 (3)	0.5522 (3)	0.0620 (10)
H12	0.8491	0.2475	0.5351	0.074*
C13	0.2916 (5)	0.2082 (3)	0.5485 (3)	0.0708 (12)
H13A	0.2840	0.2797	0.5239	0.106*
H13B	0.2167	0.2069	0.6063	0.106*
H13C	0.2591	0.1615	0.5061	0.106*
C14	0.3784 (7)	0.0013 (3)	0.6390 (3)	0.0865 (15)
H14A	0.2969	0.0369	0.6869	0.130*
H14B	0.4316	−0.0640	0.6627	0.130*
H14C	0.3218	−0.0142	0.5892	0.130*
S2	0.02193 (11)	0.85930 (7)	0.11713 (6)	0.0481 (2)
O1	−0.0211 (3)	0.97056 (19)	0.13593 (18)	0.0594 (7)
O2	−0.0880 (3)	0.7857 (2)	0.15857 (19)	0.0648 (7)
O3	0.3080 (3)	0.9908 (2)	0.0211 (2)	0.0657 (7)
O4	0.3890 (4)	1.0547 (2)	0.1388 (2)	0.0822 (9)
N3	0.0419 (4)	0.8477 (2)	0.0069 (2)	0.0509 (7)
H3N	0.091 (4)	0.897 (2)	−0.022 (2)	0.061*
N4	0.3487 (4)	0.9821 (2)	0.0977 (2)	0.0534 (8)
C15	0.2213 (4)	0.8163 (3)	0.1527 (2)	0.0434 (8)
C16	0.3568 (4)	0.8767 (3)	0.1430 (2)	0.0447 (8)
C17	0.5065 (5)	0.8400 (3)	0.1742 (3)	0.0572 (10)
H17	0.5952	0.8815	0.1671	0.069*
C18	0.5242 (5)	0.7411 (3)	0.2163 (3)	0.0650 (11)
H18	0.6259	0.7152	0.2368	0.078*
C19	0.3936 (6)	0.6811 (3)	0.2282 (3)	0.0643 (11)
H19	0.4065	0.6146	0.2570	0.077*
C20	0.2406 (5)	0.7184 (3)	0.1975 (2)	0.0543 (9)
H20	0.1511	0.6774	0.2071	0.065*
C21	0.0992 (6)	0.7447 (3)	−0.0398 (3)	0.0652 (8)
C22	−0.0109 (7)	0.6796 (3)	−0.0580 (3)	0.0756 (10)
C23	0.0528 (8)	0.5828 (3)	−0.1033 (3)	0.0824 (11)
C24	0.2297 (9)	0.5572 (4)	−0.1317 (3)	0.1028 (14)
H24	0.2724	0.4932	−0.1617	0.123*
C25	0.3376 (9)	0.6261 (5)	−0.1152 (4)	0.1085 (16)
H25	0.4535	0.6084	−0.1358	0.130*
C26	0.2839 (7)	0.7197 (4)	−0.0697 (3)	0.0804 (10)
H26	0.3598	0.7654	−0.0583	0.096*
C27	−0.1925 (7)	0.7109 (4)	−0.0284 (3)	0.0878 (12)
H27A	−0.2364	0.6588	0.0146	0.132*
H27B	−0.2505	0.7151	−0.0809	0.132*
H27C	−0.2102	0.7794	0.0006	0.132*
C28	−0.0634 (10)	0.5087 (4)	−0.1236 (4)	0.124 (2)
H28A	−0.1409	0.5443	−0.1616	0.186*
H28B	−0.1265	0.4858	−0.0670	0.186*
H28C	0.0015	0.4477	−0.1554	0.186*

	U11	U22	U33	U12	U13	U23
S1	0.0351 (4)	0.0445 (5)	0.0468 (5)	0.0025 (3)	−0.0089 (3)	0.0013 (4)
O5	0.0494 (14)	0.0469 (14)	0.0596 (16)	0.0113 (11)	−0.0094 (11)	0.0082 (11)
O6	0.0397 (13)	0.0690 (16)	0.0628 (16)	−0.0087 (12)	−0.0150 (11)	−0.0083 (13)
O7	0.0597 (16)	0.0675 (18)	0.0631 (18)	−0.0091 (13)	−0.0023 (14)	−0.0225 (14)
O8	0.121 (3)	0.0455 (16)	0.096 (2)	−0.0205 (17)	0.009 (2)	−0.0026 (16)
N1	0.0487 (16)	0.0413 (16)	0.0442 (17)	−0.0036 (13)	−0.0029 (13)	−0.0016 (12)
N2	0.0528 (18)	0.0457 (18)	0.059 (2)	−0.0038 (14)	−0.0128 (16)	−0.0060 (15)
C1	0.0358 (16)	0.0378 (17)	0.0368 (17)	0.0033 (13)	−0.0091 (13)	0.0014 (13)
C2	0.0436 (18)	0.0376 (17)	0.0385 (18)	−0.0004 (14)	−0.0108 (14)	−0.0010 (13)
C3	0.0368 (18)	0.054 (2)	0.058 (2)	−0.0060 (15)	−0.0127 (16)	−0.0012 (17)
C4	0.0373 (19)	0.059 (2)	0.060 (2)	0.0084 (16)	−0.0090 (16)	−0.0070 (18)
C5	0.050 (2)	0.044 (2)	0.054 (2)	0.0068 (16)	−0.0076 (17)	−0.0082 (16)
C6	0.0427 (18)	0.0430 (19)	0.0464 (19)	−0.0058 (15)	−0.0099 (15)	−0.0005 (15)
C7	0.060 (2)	0.0387 (18)	0.0400 (19)	−0.0022 (16)	0.0001 (16)	−0.0016 (14)
C8	0.058 (2)	0.048 (2)	0.046 (2)	−0.0024 (17)	0.0030 (17)	−0.0060 (16)
C9	0.084 (3)	0.045 (2)	0.042 (2)	−0.005 (2)	−0.0016 (19)	−0.0009 (16)
C10	0.102 (4)	0.060 (3)	0.056 (3)	0.001 (3)	−0.003 (2)	0.006 (2)
C11	0.072 (3)	0.086 (3)	0.070 (3)	0.012 (3)	−0.015 (2)	0.013 (2)
C12	0.066 (3)	0.064 (3)	0.051 (2)	0.005 (2)	−0.0094 (19)	0.0092 (19)
C13	0.062 (3)	0.067 (3)	0.082 (3)	−0.011 (2)	−0.006 (2)	−0.003 (2)
C14	0.123 (4)	0.060 (3)	0.075 (3)	−0.030 (3)	0.001 (3)	0.004 (2)
S2	0.0398 (5)	0.0510 (5)	0.0532 (5)	−0.0027 (4)	−0.0099 (4)	0.0027 (4)
O1	0.0505 (15)	0.0545 (15)	0.0684 (17)	0.0094 (12)	−0.0072 (12)	−0.0072 (13)
O2	0.0489 (15)	0.0765 (18)	0.0721 (18)	−0.0202 (13)	−0.0129 (13)	0.0186 (14)
O3	0.0609 (17)	0.0663 (18)	0.0726 (19)	−0.0141 (13)	−0.0165 (15)	0.0145 (14)
O4	0.096 (2)	0.0583 (18)	0.093 (2)	−0.0181 (16)	−0.0072 (18)	−0.0174 (16)
N3	0.0561 (19)	0.0487 (15)	0.0506 (18)	−0.0072 (13)	−0.0181 (15)	0.0080 (12)
N4	0.0405 (17)	0.0504 (19)	0.066 (2)	−0.0044 (14)	0.0013 (15)	−0.0054 (16)
C15	0.0411 (18)	0.0443 (19)	0.0436 (19)	0.0023 (15)	−0.0087 (14)	−0.0044 (15)
C16	0.0402 (18)	0.0479 (19)	0.0440 (19)	0.0029 (15)	−0.0058 (14)	−0.0096 (15)
C17	0.041 (2)	0.065 (2)	0.064 (2)	0.0031 (17)	−0.0093 (17)	−0.017 (2)
C18	0.056 (2)	0.077 (3)	0.059 (2)	0.014 (2)	−0.021 (2)	−0.009 (2)
C19	0.075 (3)	0.056 (2)	0.060 (3)	0.012 (2)	−0.022 (2)	0.0044 (19)
C20	0.060 (2)	0.052 (2)	0.051 (2)	−0.0042 (18)	−0.0131 (18)	0.0023 (17)
C21	0.0985 (19)	0.0527 (17)	0.047 (2)	−0.0022 (15)	−0.0262 (19)	0.0070 (15)
C22	0.1152 (19)	0.056 (2)	0.060 (3)	−0.0115 (17)	−0.027 (2)	0.0067 (16)
C23	0.160 (3)	0.0523 (19)	0.038 (2)	−0.012 (2)	−0.030 (2)	0.0094 (15)
C24	0.167 (4)	0.073 (3)	0.061 (3)	0.011 (2)	−0.017 (3)	−0.002 (2)
C25	0.130 (3)	0.100 (4)	0.084 (4)	0.018 (2)	−0.008 (3)	−0.019 (3)
C26	0.0994 (19)	0.082 (3)	0.056 (3)	0.011 (2)	−0.019 (2)	0.000 (2)
C27	0.1075 (19)	0.092 (3)	0.068 (3)	−0.023 (2)	−0.019 (2)	0.019 (2)
C28	0.210 (7)	0.094 (4)	0.077 (4)	−0.045 (4)	−0.030 (4)	0.016 (3)

S1—O6	1.426 (2)	S2—O2	1.424 (3)
S1—O5	1.431 (2)	S2—O1	1.427 (2)
S1—N1	1.608 (3)	S2—N3	1.613 (3)
S1—C1	1.780 (3)	S2—C15	1.774 (3)
O7—N2	1.216 (4)	O3—N4	1.220 (4)
O8—N2	1.218 (4)	O4—N4	1.219 (4)
N1—C7	1.458 (4)	N3—C21	1.474 (5)
N1—H1N	0.829 (18)	N3—H3N	0.846 (18)
N2—C2	1.470 (4)	N4—C16	1.469 (4)
C1—C6	1.385 (4)	C15—C20	1.385 (5)
C1—C2	1.394 (4)	C15—C16	1.396 (5)
C2—C3	1.371 (4)	C16—C17	1.372 (5)
C3—C4	1.377 (5)	C17—C18	1.377 (5)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.373 (5)	C18—C19	1.360 (6)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.375 (5)	C19—C20	1.394 (5)
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.382 (5)	C21—C22	1.346 (6)
C7—C12	1.405 (5)	C21—C26	1.472 (7)
C8—C9	1.409 (5)	C22—C23	1.406 (6)
C8—C13	1.485 (5)	C22—C27	1.457 (7)
C9—C10	1.384 (6)	C23—C24	1.411 (8)
C9—C14	1.495 (6)	C23—C28	1.475 (7)
C10—C11	1.363 (6)	C24—C25	1.360 (8)
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.374 (5)	C25—C26	1.361 (6)
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
O6—S1—O5	119.75 (15)	O2—S2—O1	119.82 (16)
O6—S1—N1	107.92 (16)	O2—S2—N3	107.96 (17)
O5—S1—N1	106.93 (14)	O1—S2—N3	106.38 (16)
O6—S1—C1	105.38 (14)	O2—S2—C15	105.30 (16)
O5—S1—C1	108.58 (15)	O1—S2—C15	108.09 (15)
N1—S1—C1	107.78 (15)	N3—S2—C15	108.98 (16)
C7—N1—S1	121.6 (2)	C21—N3—S2	122.4 (2)
C7—N1—H1N	114 (3)	C21—N3—H3N	111 (3)
S1—N1—H1N	113 (3)	S2—N3—H3N	112 (3)
O7—N2—O8	124.1 (3)	O4—N4—O3	124.5 (3)
O7—N2—C2	118.5 (3)	O4—N4—C16	116.9 (3)
O8—N2—C2	117.3 (3)	O3—N4—C16	118.5 (3)
C6—C1—C2	117.7 (3)	C20—C15—C16	117.8 (3)
C6—C1—S1	117.5 (2)	C20—C15—S2	117.6 (3)
C2—C1—S1	124.8 (2)	C16—C15—S2	124.5 (3)
C3—C2—C1	121.6 (3)	C17—C16—C15	121.7 (3)
C3—C2—N2	116.0 (3)	C17—C16—N4	116.2 (3)
C1—C2—N2	122.4 (3)	C15—C16—N4	122.1 (3)
C2—C3—C4	119.4 (3)	C16—C17—C18	119.4 (4)
C2—C3—H3	120.3	C16—C17—H17	120.3
C4—C3—H3	120.3	C18—C17—H17	120.3
C5—C4—C3	120.1 (3)	C19—C18—C17	120.3 (4)
C5—C4—H4	120.0	C19—C18—H18	119.8
C3—C4—H4	120.0	C17—C18—H18	119.8
C4—C5—C6	120.4 (3)	C18—C19—C20	120.6 (4)
C4—C5—H5	119.8	C18—C19—H19	119.7
C6—C5—H5	119.8	C20—C19—H19	119.7
C5—C6—C1	120.8 (3)	C15—C20—C19	120.2 (4)
C5—C6—H6	119.6	C15—C20—H20	119.9
C1—C6—H6	119.6	C19—C20—H20	119.9
C8—C7—C12	122.1 (3)	C22—C21—C26	121.8 (4)
C8—C7—N1	120.2 (3)	C22—C21—N3	122.2 (4)
C12—C7—N1	117.6 (3)	C26—C21—N3	115.9 (4)
C7—C8—C9	118.3 (4)	C21—C22—C23	119.1 (5)
C7—C8—C13	121.3 (3)	C21—C22—C27	118.8 (4)
C9—C8—C13	120.4 (4)	C23—C22—C27	122.0 (5)
C10—C9—C8	118.2 (4)	C22—C23—C24	119.7 (5)
C10—C9—C14	120.1 (4)	C22—C23—C28	120.8 (6)
C8—C9—C14	121.6 (4)	C24—C23—C28	119.4 (5)
C11—C10—C9	123.2 (4)	C25—C24—C23	119.9 (5)
C11—C10—H10	118.4	C25—C24—H24	120.0
C9—C10—H10	118.4	C23—C24—H24	120.0
C10—C11—C12	119.6 (4)	C24—C25—C26	123.0 (6)
C10—C11—H11	120.2	C24—C25—H25	118.5
C12—C11—H11	120.2	C26—C25—H25	118.5
C11—C12—C7	118.6 (4)	C25—C26—C21	116.3 (5)
C11—C12—H12	120.7	C25—C26—H26	121.8
C7—C12—H12	120.7	C21—C26—H26	121.8
C8—C13—H13A	109.5	C22—C27—H27A	109.5
C8—C13—H13B	109.5	C22—C27—H27B	109.5
H13A—C13—H13B	109.5	H27A—C27—H27B	109.5
C8—C13—H13C	109.5	C22—C27—H27C	109.5
H13A—C13—H13C	109.5	H27A—C27—H27C	109.5
H13B—C13—H13C	109.5	H27B—C27—H27C	109.5
C9—C14—H14A	109.5	C23—C28—H28A	109.5
C9—C14—H14B	109.5	C23—C28—H28B	109.5
H14A—C14—H14B	109.5	H28A—C28—H28B	109.5
C9—C14—H14C	109.5	C23—C28—H28C	109.5
H14A—C14—H14C	109.5	H28A—C28—H28C	109.5
H14B—C14—H14C	109.5	H28B—C28—H28C	109.5
O6—S1—N1—C7	53.0 (3)	O2—S2—N3—C21	−55.1 (3)
O5—S1—N1—C7	−177.0 (3)	O1—S2—N3—C21	175.1 (3)
C1—S1—N1—C7	−60.4 (3)	C15—S2—N3—C21	58.8 (3)
O6—S1—C1—C6	−10.1 (3)	O2—S2—C15—C20	9.5 (3)
O5—S1—C1—C6	−139.6 (2)	O1—S2—C15—C20	138.7 (3)
N1—S1—C1—C6	104.9 (3)	N3—S2—C15—C20	−106.1 (3)
O6—S1—C1—C2	169.9 (3)	O2—S2—C15—C16	−166.9 (3)
O5—S1—C1—C2	40.5 (3)	O1—S2—C15—C16	−37.7 (3)
N1—S1—C1—C2	−75.0 (3)	N3—S2—C15—C16	77.5 (3)
C6—C1—C2—C3	−2.3 (5)	C20—C15—C16—C17	1.8 (5)
S1—C1—C2—C3	177.7 (3)	S2—C15—C16—C17	178.2 (3)
C6—C1—C2—N2	177.9 (3)	C20—C15—C16—N4	−179.2 (3)
S1—C1—C2—N2	−2.1 (4)	S2—C15—C16—N4	−2.8 (5)
O7—N2—C2—C3	−126.1 (3)	O4—N4—C16—C17	−50.8 (4)
O8—N2—C2—C3	50.4 (4)	O3—N4—C16—C17	126.9 (3)
O7—N2—C2—C1	53.8 (4)	O4—N4—C16—C15	130.2 (3)
O8—N2—C2—C1	−129.7 (4)	O3—N4—C16—C15	−52.2 (4)
C1—C2—C3—C4	0.7 (5)	C15—C16—C17—C18	0.0 (5)
N2—C2—C3—C4	−179.4 (3)	N4—C16—C17—C18	−179.1 (3)
C2—C3—C4—C5	1.0 (5)	C16—C17—C18—C19	−1.1 (6)
C3—C4—C5—C6	−1.1 (6)	C17—C18—C19—C20	0.4 (6)
C4—C5—C6—C1	−0.4 (5)	C16—C15—C20—C19	−2.4 (5)
C2—C1—C6—C5	2.1 (5)	S2—C15—C20—C19	−179.1 (3)
S1—C1—C6—C5	−177.9 (3)	C18—C19—C20—C15	1.4 (6)
S1—N1—C7—C8	−97.5 (3)	S2—N3—C21—C22	92.1 (4)
S1—N1—C7—C12	84.6 (4)	S2—N3—C21—C26	−90.9 (4)
C12—C7—C8—C9	−0.1 (5)	C26—C21—C22—C23	2.8 (6)
N1—C7—C8—C9	−177.9 (3)	N3—C21—C22—C23	179.6 (3)
C12—C7—C8—C13	178.6 (3)	C26—C21—C22—C27	−178.3 (4)
N1—C7—C8—C13	0.8 (5)	N3—C21—C22—C27	−1.6 (6)
C7—C8—C9—C10	−0.9 (5)	C21—C22—C23—C24	−2.1 (6)
C13—C8—C9—C10	−179.6 (4)	C27—C22—C23—C24	179.1 (4)
C7—C8—C9—C14	176.7 (3)	C21—C22—C23—C28	179.3 (4)
C13—C8—C9—C14	−2.0 (6)	C27—C22—C23—C28	0.5 (6)
C8—C9—C10—C11	1.3 (6)	C22—C23—C24—C25	0.0 (7)
C14—C9—C10—C11	−176.3 (4)	C28—C23—C24—C25	178.6 (5)
C9—C10—C11—C12	−0.8 (7)	C23—C24—C25—C26	1.6 (8)
C10—C11—C12—C7	−0.2 (6)	C24—C25—C26—C21	−0.9 (8)
C8—C7—C12—C11	0.6 (6)	C22—C21—C26—C25	−1.3 (6)
N1—C7—C12—C11	178.5 (3)	N3—C21—C26—C25	−178.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O5i	0.83 (2)	2.36 (3)	3.056 (4)	142 (3)
N1—H1N···O7	0.83 (2)	2.45 (3)	3.011 (4)	126 (3)
N3—H3N···O3	0.85 (2)	2.40 (3)	3.012 (4)	129 (3)
N3—H3N···O1ii	0.85 (2)	2.41 (3)	3.070 (4)	135 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O5i	0.83 (2)	2.36 (3)	3.056 (4)	142 (3)
N1—H1N⋯O7	0.83 (2)	2.45 (3)	3.011 (4)	126 (3)
N3—H3N⋯O3	0.85 (2)	2.40 (3)	3.012 (4)	129 (3)
N3—H3N⋯O1ii	0.85 (2)	2.41 (3)	3.070 (4)	135 (3)

Symmetry codes: (i) ; (ii) .