N-(3,5-Dimethyl-phen-yl)-2-nitro-benzene-sulfonamide.

The asymmetric unit of the title compound, C(14)H(14)N(2)O(4)S, consists of two crystallographically independent mol-ecules. The mol-ecules are twisted at the S-N bonds with C-S-N-C torsion angles of 44.2 (3) and -49.3 (3)°. The dihedral angles between the benzene rings in the two mol-ecules are 71.53 (7) and 72.11 (7)°. The amide H atoms exhibit bifurcated intra- and inter-molecular hydrogen bonds; the intra-molecular N-H⋯O(N) hydrogen bonds generate S(7) motifs. In the crystal, the independent mol-ecules are separately connected through the inter-molecular N-H⋯O(S) hydrogen bonds, generating a C(4) motif and a helical chain along the b axis for one mol-ecule and an R(2) (2)(8) motif and an inversion dimer for the other. The crystal studied was a pseudo-merohedral twin with twin law (-100/0-10/001), the refined ratio of the twin domains being 0.7876 (12):0.2124 (12).

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda & Weiss (1994 ▶); Shahwar et al. (2012 ▶), of N-aryl­sulfonamides, see: Chaithanya et al. (2012 ▶) and of N-chloro­aryl­sulfonamides, see: Shetty & Gowda (2004 ▶). For hydrogen-bonding patterns and motifs, see: Adsmond et al. (2001 ▶),

Experimental

Crystal data

C14H14N2O4S

M = 306.33

Monoclinic,

a = 16.561 (1) Å

b = 8.1611 (6) Å

c = 21.476 (2) Å

β = 90.056 (7)°

V = 2902.6 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 293 K

0.48 × 0.40 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.894, T max = 0.954

12941 measured reflections

5929 independent reflections

4004 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.123

S = 1.00

5929 reflections

390 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis n class="Disease">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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812036926/is5184sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036926/is5184Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812036926/is5184Isup3.cml

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

C14H14N2O4S	F(000) = 1280
Mr = 306.33	Dx = 1.402 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2953 reflections
a = 16.561 (1) Å	θ = 2.5–27.9°
b = 8.1611 (6) Å	µ = 0.24 mm−1
c = 21.476 (2) Å	T = 293 K
β = 90.056 (7)°	Prism, brown
V = 2902.6 (4) Å3	0.48 × 0.40 × 0.20 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	5929 independent reflections
Radiation source: fine-focus sealed tube	4004 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −20→20
Tmin = 0.894, Tmax = 0.954	k = −10→5
12941 measured reflections	l = −19→26

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0703P)2] where P = (Fo2 + 2Fc2)/3
5929 reflections	(Δ/σ)max = 0.006
390 parameters	Δρmax = 0.32 e Å−3
6 restraints	Δρmin = −0.29 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	0.10145 (4)	0.28567 (9)	0.27572 (3)	0.0436 (2)
O1	0.09244 (13)	0.4509 (3)	0.25622 (10)	0.0612 (6)
O2	0.13065 (14)	0.1683 (3)	0.23195 (10)	0.0648 (6)
O3	0.11511 (16)	−0.0493 (3)	0.33802 (14)	0.0830 (8)
O4	0.23948 (19)	−0.1115 (4)	0.34483 (18)	0.1090 (11)
N1	0.01449 (14)	0.2232 (3)	0.30039 (11)	0.0451 (6)
H1N	0.0052 (18)	0.127 (2)	0.2925 (14)	0.054*
N2	0.18483 (18)	−0.0130 (3)	0.34824 (13)	0.0597 (7)
C1	0.16894 (15)	0.2911 (3)	0.34040 (13)	0.0390 (6)
C2	0.20431 (17)	0.1548 (4)	0.36690 (13)	0.0459 (7)
C3	0.26122 (18)	0.1709 (5)	0.41434 (16)	0.0614 (9)
H3	0.2854	0.0785	0.4315	0.074*
C4	0.2813 (2)	0.3250 (6)	0.43555 (16)	0.0657 (10)
H4	0.3182	0.3364	0.4680	0.079*
C5	0.24775 (18)	0.4600 (5)	0.40949 (17)	0.0634 (10)
H5	0.2625	0.5635	0.4236	0.076*
C6	0.19187 (17)	0.4449 (4)	0.36223 (14)	0.0513 (8)
H6	0.1692	0.5384	0.3447	0.062*
C7	−0.02146 (14)	0.2819 (3)	0.35635 (13)	0.0374 (6)
C8	−0.02904 (17)	0.4483 (4)	0.36658 (14)	0.0454 (7)
H8	−0.0092	0.5225	0.3375	0.054*
C9	−0.06662 (18)	0.5047 (4)	0.42075 (16)	0.0542 (8)
C10	−0.0970 (2)	0.3898 (4)	0.46210 (15)	0.0592 (9)
H10	−0.1228	0.4262	0.4980	0.071*
C11	−0.09039 (19)	0.2245 (4)	0.45202 (15)	0.0538 (8)
C12	−0.05146 (17)	0.1705 (4)	0.39875 (14)	0.0467 (7)
H12	−0.0455	0.0588	0.3915	0.056*
C13	−0.0759 (2)	0.6871 (4)	0.4317 (2)	0.0811 (12)
H13A	−0.0327	0.7445	0.4114	0.122*
H13B	−0.0741	0.7091	0.4756	0.122*
H13C	−0.1267	0.7233	0.4151	0.122*
C14	−0.1251 (3)	0.1020 (5)	0.49760 (18)	0.0875 (13)
H14A	−0.0820	0.0517	0.5206	0.131*
H14B	−0.1545	0.0194	0.4753	0.131*
H14C	−0.1608	0.1572	0.5258	0.131*
S2	0.40323 (4)	0.72449 (9)	0.02986 (3)	0.04244 (19)
O5	0.39955 (14)	0.8897 (2)	0.01021 (10)	0.0578 (6)
O6	0.38793 (14)	0.5967 (3)	−0.01392 (9)	0.0610 (6)
O7	0.40738 (16)	0.3814 (3)	0.09201 (14)	0.0767 (7)
O8	0.28562 (16)	0.2925 (3)	0.08814 (15)	0.0886 (9)
N3	0.49231 (14)	0.6879 (3)	0.05761 (11)	0.0437 (6)
H3N	0.5007 (18)	0.588 (2)	0.0555 (14)	0.052*
N4	0.33469 (18)	0.4009 (3)	0.09653 (12)	0.0542 (6)
C15	0.33333 (15)	0.7097 (3)	0.09236 (13)	0.0386 (6)
C16	0.30457 (16)	0.5622 (4)	0.11719 (13)	0.0439 (7)
C17	0.24623 (18)	0.5593 (5)	0.16329 (15)	0.0552 (8)
H17	0.2266	0.4602	0.1784	0.066*
C18	0.21766 (18)	0.7054 (5)	0.18641 (17)	0.0616 (9)
H18	0.1798	0.7049	0.2183	0.074*
C19	0.24443 (18)	0.8513 (5)	0.16295 (16)	0.0593 (8)
H19	0.2243	0.9492	0.1787	0.071*
C20	0.30193 (17)	0.8538 (4)	0.11534 (14)	0.0489 (8)
H20	0.3191	0.9535	0.0991	0.059*
C21	0.52374 (15)	0.7656 (3)	0.11202 (12)	0.0343 (6)
C22	0.55543 (16)	0.6691 (4)	0.15836 (14)	0.0431 (7)
H22	0.5518	0.5557	0.1551	0.052*
C23	0.59271 (17)	0.7376 (4)	0.20976 (14)	0.0457 (7)
C24	0.59616 (17)	0.9071 (4)	0.21341 (14)	0.0486 (7)
H24	0.6207	0.9549	0.2479	0.058*
C25	0.56453 (16)	1.0072 (4)	0.16781 (15)	0.0452 (7)
C26	0.52802 (16)	0.9346 (4)	0.11635 (13)	0.0418 (7)
H26	0.5065	0.9996	0.0849	0.050*
C27	0.6301 (2)	0.6305 (4)	0.25904 (16)	0.0674 (10)
H27A	0.6015	0.5284	0.2611	0.101*
H27B	0.6271	0.6847	0.2986	0.101*
H27C	0.6856	0.6101	0.2488	0.101*
C28	0.5723 (2)	1.1911 (4)	0.17188 (19)	0.0668 (10)
H28A	0.5320	1.2333	0.1996	0.100*
H28B	0.5650	1.2380	0.1313	0.100*
H28C	0.6250	1.2189	0.1873	0.100*

	U11	U22	U33	U12	U13	U23
S1	0.0409 (4)	0.0553 (5)	0.0346 (4)	−0.0001 (3)	−0.0008 (3)	0.0018 (3)
O1	0.0596 (13)	0.0618 (14)	0.0622 (14)	−0.0008 (11)	0.0025 (11)	0.0275 (12)
O2	0.0650 (14)	0.0870 (17)	0.0424 (12)	0.0065 (12)	0.0043 (11)	−0.0184 (12)
O3	0.0751 (14)	0.0599 (15)	0.114 (2)	−0.0024 (13)	−0.0071 (16)	−0.0043 (15)
O4	0.096 (2)	0.0755 (19)	0.156 (3)	0.0428 (17)	0.013 (2)	0.0038 (19)
N1	0.0412 (13)	0.0502 (15)	0.0438 (14)	−0.0084 (12)	−0.0014 (11)	−0.0094 (13)
N2	0.0642 (14)	0.0532 (13)	0.0617 (17)	0.0132 (13)	0.0073 (14)	0.0081 (13)
C1	0.0330 (14)	0.0462 (17)	0.0378 (14)	0.0001 (13)	0.0039 (12)	0.0016 (14)
C2	0.0381 (15)	0.0598 (15)	0.0399 (15)	0.0035 (13)	0.0060 (13)	0.0067 (14)
C3	0.0425 (18)	0.092 (3)	0.0492 (19)	0.0106 (18)	0.0040 (15)	0.019 (2)
C4	0.0446 (18)	0.109 (3)	0.0433 (18)	−0.014 (2)	−0.0004 (15)	−0.004 (2)
C5	0.0468 (19)	0.085 (3)	0.058 (2)	−0.0163 (18)	0.0061 (17)	−0.020 (2)
C6	0.0425 (16)	0.058 (2)	0.0534 (18)	−0.0078 (15)	0.0032 (14)	−0.0068 (16)
C7	0.0261 (13)	0.0455 (17)	0.0407 (15)	0.0015 (12)	−0.0052 (11)	−0.0030 (13)
C8	0.0401 (16)	0.0463 (19)	0.0497 (17)	−0.0005 (13)	−0.0039 (14)	0.0021 (14)
C9	0.0513 (18)	0.0493 (19)	0.062 (2)	0.0106 (15)	−0.0108 (16)	−0.0082 (17)
C10	0.058 (2)	0.072 (2)	0.0484 (18)	0.0116 (18)	0.0051 (17)	−0.0093 (17)
C11	0.0498 (18)	0.067 (2)	0.0446 (17)	0.0013 (17)	0.0011 (15)	0.0028 (16)
C12	0.0428 (16)	0.0439 (18)	0.0535 (18)	−0.0011 (13)	−0.0032 (14)	0.0026 (15)
C13	0.088 (3)	0.062 (3)	0.093 (3)	0.020 (2)	−0.008 (2)	−0.017 (2)
C14	0.097 (3)	0.099 (3)	0.067 (2)	−0.014 (2)	0.020 (2)	0.020 (2)
S2	0.0462 (4)	0.0507 (4)	0.0305 (3)	−0.0034 (4)	−0.0045 (3)	0.0018 (3)
O5	0.0634 (14)	0.0569 (13)	0.0531 (12)	−0.0055 (11)	−0.0033 (11)	0.0177 (10)
O6	0.0708 (15)	0.0708 (15)	0.0413 (11)	−0.0095 (12)	−0.0052 (11)	−0.0146 (11)
O7	0.0674 (16)	0.0550 (15)	0.108 (2)	0.0121 (12)	0.0070 (15)	0.0038 (14)
O8	0.0862 (19)	0.0584 (16)	0.121 (2)	−0.0242 (14)	0.0008 (18)	−0.0154 (16)
N3	0.0415 (13)	0.0444 (15)	0.0452 (14)	0.0019 (12)	0.0028 (11)	−0.0079 (12)
N4	0.0623 (17)	0.0468 (14)	0.0534 (16)	−0.0029 (13)	−0.0035 (14)	0.0078 (12)
C15	0.0324 (14)	0.0463 (17)	0.0369 (15)	−0.0008 (13)	−0.0066 (12)	−0.0018 (13)
C16	0.0399 (15)	0.0520 (16)	0.0397 (16)	−0.0037 (13)	−0.0073 (13)	0.0024 (13)
C17	0.0470 (18)	0.068 (2)	0.0505 (19)	−0.0107 (16)	0.0006 (15)	0.0065 (17)
C18	0.0378 (16)	0.094 (2)	0.0528 (19)	−0.0051 (17)	0.0027 (15)	−0.0098 (18)
C19	0.0414 (17)	0.0705 (19)	0.066 (2)	0.0048 (14)	−0.0040 (16)	−0.0244 (17)
C20	0.0416 (16)	0.0505 (19)	0.0546 (18)	−0.0029 (14)	−0.0067 (15)	−0.0046 (15)
C21	0.0290 (13)	0.0364 (16)	0.0376 (14)	−0.0023 (11)	0.0051 (11)	0.0011 (12)
C22	0.0425 (16)	0.0376 (16)	0.0494 (17)	−0.0002 (12)	0.0025 (13)	−0.0015 (14)
C23	0.0410 (15)	0.0537 (19)	0.0424 (16)	0.0004 (14)	−0.0013 (14)	0.0041 (14)
C24	0.0442 (16)	0.0553 (19)	0.0464 (17)	−0.0043 (14)	−0.0043 (14)	−0.0058 (15)
C25	0.0410 (16)	0.0407 (17)	0.0540 (18)	−0.0055 (13)	0.0034 (14)	−0.0028 (14)
C26	0.0359 (14)	0.0437 (18)	0.0458 (16)	−0.0021 (12)	0.0015 (13)	0.0070 (14)
C27	0.071 (2)	0.073 (2)	0.058 (2)	0.0065 (19)	−0.0150 (18)	0.0135 (18)
C28	0.072 (2)	0.046 (2)	0.083 (3)	−0.0094 (16)	−0.002 (2)	−0.0081 (18)

S1—O1	1.420 (2)	S2—O5	1.414 (2)
S1—O2	1.427 (2)	S2—O6	1.427 (2)
S1—N1	1.617 (2)	S2—N3	1.618 (2)
S1—C1	1.783 (3)	S2—C15	1.777 (3)
O3—N2	1.212 (3)	O7—N4	1.218 (3)
O4—N2	1.213 (3)	O8—N4	1.215 (3)
N1—C7	1.425 (3)	N3—C21	1.427 (3)
N1—H1N	0.819 (17)	N3—H3N	0.832 (17)
N2—C2	1.463 (4)	N4—C16	1.476 (4)
C1—C2	1.379 (4)	C15—C20	1.378 (4)
C1—C6	1.392 (4)	C15—C16	1.401 (4)
C2—C3	1.393 (4)	C16—C17	1.384 (4)
C3—C4	1.378 (5)	C17—C18	1.375 (5)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.355 (5)	C18—C19	1.367 (5)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.378 (4)	C19—C20	1.398 (5)
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C7—C12	1.380 (4)	C21—C22	1.373 (4)
C7—C8	1.381 (4)	C21—C26	1.384 (4)
C8—C9	1.398 (4)	C22—C23	1.382 (4)
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.386 (5)	C23—C24	1.386 (4)
C9—C13	1.515 (4)	C23—C27	1.506 (4)
C10—C11	1.370 (5)	C24—C25	1.378 (4)
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.386 (4)	C25—C26	1.392 (4)
C11—C14	1.513 (5)	C25—C28	1.509 (4)
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
O1—S1—O2	118.60 (14)	O5—S2—O6	119.54 (13)
O1—S1—N1	107.63 (13)	O5—S2—N3	108.96 (13)
O2—S1—N1	107.85 (14)	O6—S2—N3	105.60 (13)
O1—S1—C1	105.78 (13)	O5—S2—C15	105.19 (13)
O2—S1—C1	108.50 (13)	O6—S2—C15	109.43 (13)
N1—S1—C1	108.08 (12)	N3—S2—C15	107.66 (12)
C7—N1—S1	122.89 (19)	C21—N3—S2	123.45 (19)
C7—N1—H1N	115 (2)	C21—N3—H3N	115 (2)
S1—N1—H1N	114 (2)	S2—N3—H3N	108 (2)
O3—N2—O4	122.5 (3)	O8—N4—O7	123.6 (3)
O3—N2—C2	119.2 (3)	O8—N4—C16	117.9 (3)
O4—N2—C2	118.2 (3)	O7—N4—C16	118.3 (3)
C2—C1—C6	118.2 (3)	C20—C15—C16	118.0 (3)
C2—C1—S1	124.6 (2)	C20—C15—S2	117.3 (2)
C6—C1—S1	117.1 (2)	C16—C15—S2	124.6 (2)
C1—C2—C3	120.8 (3)	C17—C16—C15	121.6 (3)
C1—C2—N2	123.2 (3)	C17—C16—N4	115.9 (3)
C3—C2—N2	115.9 (3)	C15—C16—N4	122.5 (3)
C4—C3—C2	119.4 (3)	C18—C17—C16	119.0 (3)
C4—C3—H3	120.3	C18—C17—H17	120.5
C2—C3—H3	120.3	C16—C17—H17	120.5
C5—C4—C3	120.4 (3)	C19—C18—C17	120.7 (3)
C5—C4—H4	119.8	C19—C18—H18	119.7
C3—C4—H4	119.8	C17—C18—H18	119.7
C4—C5—C6	120.4 (3)	C18—C19—C20	120.3 (3)
C4—C5—H5	119.8	C18—C19—H19	119.9
C6—C5—H5	119.8	C20—C19—H19	119.9
C5—C6—C1	120.8 (3)	C15—C20—C19	120.5 (3)
C5—C6—H6	119.6	C15—C20—H20	119.8
C1—C6—H6	119.6	C19—C20—H20	119.8
C12—C7—C8	120.7 (3)	C22—C21—C26	120.2 (3)
C12—C7—N1	119.1 (3)	C22—C21—N3	118.5 (2)
C8—C7—N1	120.2 (3)	C26—C21—N3	121.1 (2)
C7—C8—C9	119.8 (3)	C21—C22—C23	121.1 (3)
C7—C8—H8	120.1	C21—C22—H22	119.4
C9—C8—H8	120.1	C23—C22—H22	119.4
C10—C9—C8	118.2 (3)	C22—C23—C24	117.8 (3)
C10—C9—C13	121.9 (3)	C22—C23—C27	120.6 (3)
C8—C9—C13	119.9 (3)	C24—C23—C27	121.5 (3)
C11—C10—C9	122.4 (3)	C25—C24—C23	122.4 (3)
C11—C10—H10	118.8	C25—C24—H24	118.8
C9—C10—H10	118.8	C23—C24—H24	118.8
C10—C11—C12	118.7 (3)	C24—C25—C26	118.5 (3)
C10—C11—C14	121.2 (3)	C24—C25—C28	121.0 (3)
C12—C11—C14	120.1 (3)	C26—C25—C28	120.4 (3)
C7—C12—C11	120.2 (3)	C21—C26—C25	120.0 (3)
C7—C12—H12	119.9	C21—C26—H26	120.0
C11—C12—H12	119.9	C25—C26—H26	120.0
C9—C13—H13A	109.5	C23—C27—H27A	109.5
C9—C13—H13B	109.5	C23—C27—H27B	109.5
H13A—C13—H13B	109.5	H27A—C27—H27B	109.5
C9—C13—H13C	109.5	C23—C27—H27C	109.5
H13A—C13—H13C	109.5	H27A—C27—H27C	109.5
H13B—C13—H13C	109.5	H27B—C27—H27C	109.5
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
O1—S1—N1—C7	−69.6 (2)	O5—S2—N3—C21	64.2 (3)
O2—S1—N1—C7	161.4 (2)	O6—S2—N3—C21	−166.2 (2)
C1—S1—N1—C7	44.2 (3)	C15—S2—N3—C21	−49.3 (3)
O1—S1—C1—C2	−168.8 (2)	O5—S2—C15—C20	−10.3 (2)
O2—S1—C1—C2	−40.6 (3)	O6—S2—C15—C20	−139.9 (2)
N1—S1—C1—C2	76.1 (3)	N3—S2—C15—C20	105.8 (2)
O1—S1—C1—C6	6.1 (3)	O5—S2—C15—C16	165.8 (2)
O2—S1—C1—C6	134.3 (2)	O6—S2—C15—C16	36.2 (3)
N1—S1—C1—C6	−109.0 (2)	N3—S2—C15—C16	−78.1 (2)
C6—C1—C2—C3	0.2 (4)	C20—C15—C16—C17	0.2 (4)
S1—C1—C2—C3	175.0 (2)	S2—C15—C16—C17	−175.8 (2)
C6—C1—C2—N2	179.6 (3)	C20—C15—C16—N4	−179.3 (2)
S1—C1—C2—N2	−5.6 (4)	S2—C15—C16—N4	4.7 (4)
O3—N2—C2—C1	−41.2 (4)	O8—N4—C16—C17	43.4 (4)
O4—N2—C2—C1	140.3 (3)	O7—N4—C16—C17	−132.8 (3)
O3—N2—C2—C3	138.3 (3)	O8—N4—C16—C15	−137.1 (3)
O4—N2—C2—C3	−40.3 (4)	O7—N4—C16—C15	46.7 (4)
C1—C2—C3—C4	1.0 (4)	C15—C16—C17—C18	−1.9 (4)
N2—C2—C3—C4	−178.4 (3)	N4—C16—C17—C18	177.6 (3)
C2—C3—C4—C5	−1.7 (5)	C16—C17—C18—C19	2.1 (5)
C3—C4—C5—C6	1.3 (5)	C17—C18—C19—C20	−0.6 (5)
C4—C5—C6—C1	0.0 (5)	C16—C15—C20—C19	1.4 (4)
C2—C1—C6—C5	−0.7 (4)	S2—C15—C20—C19	177.7 (2)
S1—C1—C6—C5	−175.9 (2)	C18—C19—C20—C15	−1.2 (5)
S1—N1—C7—C12	−131.0 (2)	S2—N3—C21—C22	128.6 (2)
S1—N1—C7—C8	51.7 (3)	S2—N3—C21—C26	−56.2 (3)
C12—C7—C8—C9	0.7 (4)	C26—C21—C22—C23	−0.6 (4)
N1—C7—C8—C9	178.0 (2)	N3—C21—C22—C23	174.6 (2)
C7—C8—C9—C10	−1.5 (4)	C21—C22—C23—C24	0.8 (4)
C7—C8—C9—C13	−179.3 (3)	C21—C22—C23—C27	−177.6 (3)
C8—C9—C10—C11	0.9 (5)	C22—C23—C24—C25	−0.5 (4)
C13—C9—C10—C11	178.7 (3)	C27—C23—C24—C25	177.9 (3)
C9—C10—C11—C12	0.4 (5)	C23—C24—C25—C26	−0.1 (4)
C9—C10—C11—C14	−179.2 (3)	C23—C24—C25—C28	−177.4 (3)
C8—C7—C12—C11	0.6 (4)	C22—C21—C26—C25	0.0 (4)
N1—C7—C12—C11	−176.7 (2)	N3—C21—C26—C25	−175.1 (2)
C10—C11—C12—C7	−1.2 (4)	C24—C25—C26—C21	0.3 (4)
C14—C11—C12—C7	178.4 (3)	C28—C25—C26—C21	177.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.82 (2)	2.40 (2)	3.089 (3)	142 (3)
N1—H1N···O3	0.82 (2)	2.52 (3)	2.893 (4)	109 (2)
N3—H3N···O7	0.83 (2)	2.42 (3)	2.963 (3)	124 (3)
N3—H3N···O6ii	0.83 (2)	2.54 (2)	3.195 (3)	136 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.82 (2)	2.40 (2)	3.089 (3)	142 (3)
N1—H1N⋯O3	0.82 (2)	2.52 (3)	2.893 (4)	109 (2)
N3—H3N⋯O7	0.83 (2)	2.42 (3)	2.963 (3)	124 (3)
N3—H3N⋯O6ii	0.83 (2)	2.54 (2)	3.195 (3)	136 (3)

Symmetry codes: (i) ; (ii) .