N-(3,5-Dimethyl-phen-yl)-4-nitro-benzene-sulfonamide.

There are two independent mol-ecules in the asymmetric unit of the title compound, C14H14N2O4S, in which the dihedral angles between the benzene rings are 56.22 (15) and 58.16 (14)°. In the crystal, N-H⋯Onitro hydrogen bonds link the mol-ecules into zigzag chains running along the a-axis direction.

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 & Grant (2001 ▶).

Experimental

Crystal data

C14H14N2O4S

M = 306.33

Orthorhombic,

a = 14.708 (1) Å

b = 7.9410 (7) Å

c = 24.741 (2) Å

V = 2889.7 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 293 K

0.38 × 0.30 × 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 = 0.914, T max = 0.944

6693 measured reflections

3714 independent reflections

2624 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.074

S = 1.00

3714 reflections

390 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 1005 Friedel pairs

Flack parameter: 0.04 (8)

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/S1600536812047502/bt6865sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047502/bt6865Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812047502/bt6865Isup3.cml

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

C14H14N2O4S	F(000) = 1280
Mr = 306.33	Dx = 1.408 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1548 reflections
a = 14.708 (1) Å	θ = 2.6–27.9°
b = 7.9410 (7) Å	µ = 0.24 mm−1
c = 24.741 (2) Å	T = 293 K
V = 2889.7 (4) Å3	Prism, colourless
Z = 8	0.38 × 0.30 × 0.24 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3714 independent reflections
Radiation source: fine-focus sealed tube	2624 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Rotation method data acquisition using ω scans	θmax = 25.4°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −17→6
Tmin = 0.914, Tmax = 0.944	k = −9→7
6693 measured reflections	l = −16→29

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.039	w = 1/[σ2(Fo2) + (0.0295P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.074	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.18 e Å−3
3714 reflections	Δρmin = −0.18 e Å−3
390 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
3 restraints	Extinction coefficient: 0.0037 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1005 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.04 (8)

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
S1	0.20029 (7)	0.68335 (15)	0.47849 (4)	0.0495 (3)
O1	0.2499 (2)	0.8380 (4)	0.48316 (13)	0.0631 (9)
O2	0.1473 (2)	0.6216 (4)	0.52234 (12)	0.0710 (10)
O3	0.4490 (3)	0.0058 (6)	0.42894 (19)	0.1052 (15)
O4	0.5359 (3)	0.1925 (6)	0.3950 (2)	0.1156 (17)
N1	0.1295 (2)	0.7027 (5)	0.42794 (16)	0.0476 (9)
H1N	0.094 (2)	0.618 (3)	0.4263 (16)	0.057*
N2	0.4666 (3)	0.1511 (6)	0.41830 (18)	0.0681 (13)
C1	0.2802 (2)	0.5258 (5)	0.46126 (14)	0.0381 (9)
C2	0.2595 (3)	0.3583 (5)	0.47151 (17)	0.0517 (11)
H2	0.2046	0.3295	0.4877	0.062*
C3	0.3211 (3)	0.2352 (5)	0.4575 (2)	0.0550 (16)
H3	0.3089	0.1223	0.4643	0.066*
C4	0.4008 (3)	0.2829 (6)	0.43324 (19)	0.0481 (12)
C5	0.4228 (3)	0.4459 (6)	0.42402 (17)	0.0541 (12)
H5	0.4784	0.4739	0.4085	0.065*
C6	0.3614 (3)	0.5702 (5)	0.43812 (16)	0.0483 (11)
H6	0.3751	0.6829	0.4320	0.058*
C7	0.1582 (3)	0.7666 (5)	0.3761 (2)	0.0422 (12)
C8	0.1593 (3)	0.6614 (6)	0.33197 (19)	0.0492 (11)
H8	0.1446	0.5483	0.3364	0.059*
C9	0.1817 (3)	0.7198 (7)	0.2813 (2)	0.0553 (14)
C10	0.2049 (3)	0.8896 (7)	0.2769 (2)	0.0626 (13)
H10	0.2208	0.9325	0.2432	0.075*
C11	0.2050 (3)	0.9959 (6)	0.3212 (2)	0.0601 (13)
C12	0.1793 (3)	0.9334 (5)	0.37078 (18)	0.0504 (11)
H12	0.1763	1.0045	0.4006	0.060*
C13	0.1821 (3)	0.6099 (7)	0.2319 (2)	0.0839 (17)
H13A	0.1218	0.6037	0.2173	0.126*
H13B	0.2024	0.4989	0.2415	0.126*
H13C	0.2225	0.6568	0.2054	0.126*
C14	0.2293 (4)	1.1823 (6)	0.3147 (3)	0.103 (2)
H14A	0.2189	1.2162	0.2779	0.155*
H14B	0.2921	1.1990	0.3237	0.155*
H14C	0.1920	1.2487	0.3384	0.155*
S2	−0.03497 (7)	0.80910 (15)	0.05640 (5)	0.0475 (3)
O5	0.01620 (19)	0.6581 (3)	0.05262 (13)	0.0618 (8)
O6	−0.0860 (2)	0.8702 (4)	0.01140 (12)	0.0664 (9)
O7	0.2958 (3)	1.3138 (6)	0.1386 (2)	0.1138 (18)
O8	0.2121 (3)	1.4949 (5)	0.09994 (16)	0.0838 (11)
N3	−0.1086 (2)	0.7845 (4)	0.10462 (16)	0.0446 (10)
H3N	−0.142 (2)	0.871 (3)	0.1028 (15)	0.054*
N4	0.2285 (3)	1.3523 (6)	0.11394 (18)	0.0665 (12)
C15	0.0414 (2)	0.9711 (5)	0.07551 (14)	0.0387 (10)
C16	0.1215 (3)	0.9299 (5)	0.10135 (17)	0.0530 (11)
H16	0.1338	0.8183	0.1101	0.064*
C17	0.1833 (3)	1.0543 (6)	0.1142 (2)	0.0571 (13)
H17	0.2379	1.0285	0.1313	0.069*
C18	0.1616 (3)	1.2180 (6)	0.1009 (2)	0.0440 (12)
C19	0.0830 (3)	1.2609 (5)	0.0751 (2)	0.0486 (14)
H19	0.0707	1.3723	0.0661	0.058*
C20	0.0221 (2)	1.1340 (5)	0.06260 (17)	0.0478 (11)
H20	−0.0323	1.1600	0.0453	0.057*
C21	−0.0857 (3)	0.7124 (5)	0.1559 (2)	0.0389 (11)
C22	−0.0684 (3)	0.5420 (5)	0.16021 (18)	0.0468 (11)
H22	−0.0689	0.4750	0.1294	0.056*
C23	−0.0504 (2)	0.4699 (5)	0.2103 (2)	0.0481 (11)
C24	−0.0518 (3)	0.5743 (6)	0.2550 (2)	0.0538 (12)
H24	−0.0418	0.5267	0.2889	0.065*
C25	−0.0673 (3)	0.7446 (5)	0.2521 (2)	0.0483 (14)
C26	−0.0837 (3)	0.8133 (6)	0.2017 (2)	0.0505 (11)
H26	−0.0935	0.9285	0.1984	0.061*
C27	−0.0307 (4)	0.2842 (5)	0.2156 (2)	0.0811 (17)
H27A	−0.0110	0.2407	0.1814	0.122*
H27B	−0.0849	0.2264	0.2268	0.122*
H27C	0.0162	0.2674	0.2421	0.122*
C28	−0.0679 (3)	0.8542 (7)	0.30165 (19)	0.0821 (16)
H28A	−0.0105	0.9109	0.3048	0.123*
H28B	−0.0778	0.7856	0.3331	0.123*
H28C	−0.1157	0.9359	0.2987	0.123*

	U11	U22	U33	U12	U13	U23
S1	0.0542 (6)	0.0496 (8)	0.0446 (7)	0.0110 (6)	0.0033 (6)	−0.0041 (7)
O1	0.074 (2)	0.0460 (19)	0.069 (2)	0.0071 (18)	−0.0228 (18)	−0.0130 (19)
O2	0.077 (2)	0.086 (2)	0.0502 (19)	0.0283 (19)	0.0294 (17)	0.0126 (18)
O3	0.102 (3)	0.062 (2)	0.151 (4)	0.034 (3)	0.006 (3)	−0.027 (3)
O4	0.077 (3)	0.117 (3)	0.153 (5)	0.029 (3)	0.042 (3)	−0.034 (3)
N1	0.037 (2)	0.046 (2)	0.060 (3)	−0.0075 (18)	0.0004 (18)	0.003 (2)
N2	0.065 (3)	0.067 (3)	0.072 (3)	0.019 (3)	−0.007 (2)	−0.022 (3)
C1	0.042 (2)	0.036 (2)	0.036 (2)	0.003 (2)	0.0014 (18)	0.0015 (19)
C2	0.044 (2)	0.047 (3)	0.064 (3)	0.000 (2)	0.005 (2)	0.005 (2)
C3	0.054 (3)	0.034 (3)	0.078 (5)	0.002 (2)	−0.008 (3)	0.000 (2)
C4	0.047 (3)	0.052 (3)	0.046 (3)	0.018 (3)	0.000 (2)	−0.011 (2)
C5	0.049 (3)	0.059 (3)	0.054 (3)	−0.003 (3)	0.010 (2)	0.007 (3)
C6	0.054 (3)	0.041 (3)	0.050 (3)	−0.004 (2)	0.004 (2)	0.008 (2)
C7	0.033 (2)	0.044 (3)	0.050 (3)	0.006 (2)	−0.001 (2)	0.002 (2)
C8	0.040 (2)	0.048 (3)	0.059 (3)	−0.001 (2)	−0.001 (2)	−0.002 (3)
C9	0.050 (3)	0.065 (3)	0.051 (4)	−0.001 (3)	−0.002 (3)	−0.006 (3)
C10	0.066 (3)	0.072 (4)	0.050 (3)	−0.001 (3)	0.004 (2)	0.012 (3)
C11	0.066 (3)	0.051 (3)	0.063 (3)	0.000 (2)	−0.005 (3)	0.013 (3)
C12	0.054 (3)	0.044 (3)	0.053 (3)	0.000 (2)	−0.009 (2)	−0.008 (2)
C13	0.076 (3)	0.107 (4)	0.069 (4)	−0.007 (3)	0.011 (3)	−0.026 (3)
C14	0.145 (5)	0.058 (3)	0.107 (5)	−0.010 (4)	0.005 (4)	0.026 (4)
S2	0.0512 (6)	0.0443 (7)	0.0471 (7)	−0.0100 (6)	0.0015 (6)	−0.0028 (7)
O5	0.070 (2)	0.0401 (17)	0.075 (2)	−0.0035 (16)	0.0198 (18)	−0.0141 (18)
O6	0.073 (2)	0.078 (2)	0.0489 (19)	−0.0261 (18)	−0.0172 (16)	0.0081 (18)
O7	0.074 (3)	0.095 (3)	0.173 (5)	−0.004 (3)	−0.053 (3)	−0.046 (3)
O8	0.099 (3)	0.058 (2)	0.094 (3)	−0.029 (2)	0.007 (2)	−0.014 (2)
N3	0.039 (2)	0.041 (2)	0.054 (3)	0.0005 (17)	0.0038 (18)	0.003 (2)
N4	0.057 (3)	0.070 (3)	0.073 (3)	−0.013 (3)	0.005 (2)	−0.036 (3)
C15	0.038 (2)	0.036 (2)	0.042 (2)	0.002 (2)	−0.0009 (19)	−0.0019 (19)
C16	0.056 (3)	0.047 (3)	0.056 (3)	0.006 (2)	−0.008 (2)	0.009 (2)
C17	0.042 (3)	0.063 (3)	0.066 (3)	−0.003 (3)	−0.018 (2)	−0.011 (3)
C18	0.036 (2)	0.043 (3)	0.053 (3)	−0.004 (2)	0.005 (2)	−0.019 (2)
C19	0.051 (3)	0.036 (3)	0.059 (4)	0.005 (2)	0.004 (2)	−0.004 (2)
C20	0.039 (2)	0.044 (2)	0.061 (3)	0.005 (2)	−0.009 (2)	−0.002 (2)
C21	0.032 (2)	0.040 (3)	0.045 (3)	−0.002 (2)	0.0048 (19)	−0.003 (3)
C22	0.046 (2)	0.037 (3)	0.057 (3)	−0.006 (2)	0.003 (2)	−0.008 (2)
C23	0.052 (3)	0.031 (2)	0.062 (3)	−0.005 (2)	−0.001 (2)	0.003 (2)
C24	0.049 (3)	0.064 (3)	0.048 (3)	−0.005 (2)	−0.002 (2)	0.011 (3)
C25	0.044 (3)	0.049 (3)	0.051 (4)	0.001 (2)	−0.003 (3)	−0.009 (2)
C26	0.042 (2)	0.039 (3)	0.070 (4)	−0.004 (2)	0.004 (2)	−0.008 (3)
C27	0.108 (4)	0.051 (3)	0.084 (4)	0.006 (3)	−0.017 (3)	0.007 (3)
C28	0.086 (4)	0.101 (4)	0.059 (4)	0.017 (3)	−0.001 (3)	−0.029 (3)

S1—O2	1.423 (3)	S2—O5	1.419 (3)
S1—O1	1.433 (3)	S2—O6	1.428 (3)
S1—N1	1.634 (4)	S2—N3	1.623 (4)
S1—C1	1.769 (4)	S2—C15	1.772 (4)
O3—N2	1.211 (5)	O7—N4	1.203 (5)
O4—N2	1.216 (5)	O8—N4	1.208 (5)
N1—C7	1.442 (6)	N3—C21	1.433 (6)
N1—H1N	0.849 (18)	N3—H3N	0.843 (18)
N2—C4	1.473 (6)	N4—C18	1.486 (6)
C1—C6	1.371 (5)	C15—C20	1.363 (5)
C1—C2	1.388 (5)	C15—C16	1.379 (5)
C2—C3	1.378 (6)	C16—C17	1.380 (6)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.369 (7)	C17—C18	1.378 (6)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.354 (5)	C18—C19	1.364 (6)
C5—C6	1.382 (5)	C19—C20	1.383 (5)
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C7—C12	1.366 (5)	C21—C22	1.380 (5)
C7—C8	1.376 (6)	C21—C26	1.387 (6)
C8—C9	1.376 (7)	C22—C23	1.391 (5)
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.395 (6)	C23—C24	1.382 (6)
C9—C13	1.502 (7)	C23—C27	1.509 (5)
C10—C11	1.383 (6)	C24—C25	1.373 (5)
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.376 (6)	C25—C26	1.382 (7)
C11—C14	1.532 (6)	C25—C28	1.504 (7)
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
O2—S1—O1	120.9 (2)	O5—S2—O6	121.0 (2)
O2—S1—N1	105.49 (19)	O5—S2—N3	107.50 (19)
O1—S1—N1	107.79 (19)	O6—S2—N3	105.3 (2)
O2—S1—C1	107.69 (18)	O5—S2—C15	107.14 (17)
O1—S1—C1	106.67 (18)	O6—S2—C15	107.14 (17)
N1—S1—C1	107.78 (19)	N3—S2—C15	108.30 (19)
C7—N1—S1	121.8 (3)	C21—N3—S2	122.8 (3)
C7—N1—H1N	115 (3)	C21—N3—H3N	121 (3)
S1—N1—H1N	110 (3)	S2—N3—H3N	104 (3)
O3—N2—O4	122.6 (5)	O7—N4—O8	123.2 (5)
O3—N2—C4	118.8 (5)	O7—N4—C18	118.2 (5)
O4—N2—C4	118.6 (5)	O8—N4—C18	118.6 (5)
C6—C1—C2	120.9 (4)	C20—C15—C16	120.8 (4)
C6—C1—S1	119.9 (3)	C20—C15—S2	119.6 (3)
C2—C1—S1	119.2 (3)	C16—C15—S2	119.5 (3)
C3—C2—C1	119.3 (4)	C15—C16—C17	119.9 (4)
C3—C2—H2	120.3	C15—C16—H16	120.0
C1—C2—H2	120.3	C17—C16—H16	120.0
C4—C3—C2	118.5 (4)	C18—C17—C16	117.9 (4)
C4—C3—H3	120.8	C18—C17—H17	121.0
C2—C3—H3	120.8	C16—C17—H17	121.0
C5—C4—C3	122.9 (4)	C19—C18—C17	122.9 (4)
C5—C4—N2	118.6 (4)	C19—C18—N4	118.9 (4)
C3—C4—N2	118.4 (5)	C17—C18—N4	118.2 (4)
C4—C5—C6	118.9 (4)	C18—C19—C20	118.2 (4)
C4—C5—H5	120.5	C18—C19—H19	120.9
C6—C5—H5	120.5	C20—C19—H19	120.9
C1—C6—C5	119.4 (4)	C15—C20—C19	120.2 (4)
C1—C6—H6	120.3	C15—C20—H20	119.9
C5—C6—H6	120.3	C19—C20—H20	119.9
C12—C7—C8	120.6 (5)	C22—C21—C26	120.0 (5)
C12—C7—N1	119.6 (5)	C22—C21—N3	120.2 (4)
C8—C7—N1	119.7 (4)	C26—C21—N3	119.8 (4)
C7—C8—C9	121.4 (5)	C21—C22—C23	120.5 (4)
C7—C8—H8	119.3	C21—C22—H22	119.8
C9—C8—H8	119.3	C23—C22—H22	119.8
C8—C9—C10	117.1 (5)	C24—C23—C22	117.6 (4)
C8—C9—C13	123.1 (5)	C24—C23—C27	121.3 (5)
C10—C9—C13	119.8 (5)	C22—C23—C27	121.1 (4)
C11—C10—C9	121.9 (5)	C25—C24—C23	123.4 (5)
C11—C10—H10	119.0	C25—C24—H24	118.3
C9—C10—H10	119.0	C23—C24—H24	118.3
C12—C11—C10	119.1 (4)	C24—C25—C26	117.8 (5)
C12—C11—C14	120.4 (5)	C24—C25—C28	121.8 (5)
C10—C11—C14	120.5 (5)	C26—C25—C28	120.4 (4)
C7—C12—C11	119.9 (5)	C25—C26—C21	120.8 (4)
C7—C12—H12	120.1	C25—C26—H26	119.6
C11—C12—H12	120.1	C21—C26—H26	119.6
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
O2—S1—N1—C7	178.5 (3)	O5—S2—N3—C21	44.9 (4)
O1—S1—N1—C7	48.1 (4)	O6—S2—N3—C21	175.1 (3)
C1—S1—N1—C7	−66.7 (4)	C15—S2—N3—C21	−70.6 (4)
O2—S1—C1—C6	−152.5 (3)	O5—S2—C15—C20	154.9 (3)
O1—S1—C1—C6	−21.4 (4)	O6—S2—C15—C20	23.6 (4)
N1—S1—C1—C6	94.1 (3)	N3—S2—C15—C20	−89.4 (3)
O2—S1—C1—C2	27.4 (4)	O5—S2—C15—C16	−22.5 (4)
O1—S1—C1—C2	158.5 (3)	O6—S2—C15—C16	−153.7 (3)
N1—S1—C1—C2	−85.9 (3)	N3—S2—C15—C16	93.2 (3)
C6—C1—C2—C3	−0.9 (6)	C20—C15—C16—C17	−0.3 (6)
S1—C1—C2—C3	179.2 (3)	S2—C15—C16—C17	177.1 (3)
C1—C2—C3—C4	−0.7 (7)	C15—C16—C17—C18	0.7 (7)
C2—C3—C4—C5	2.2 (7)	C16—C17—C18—C19	−1.1 (7)
C2—C3—C4—N2	180.0 (4)	C16—C17—C18—N4	−179.1 (4)
O3—N2—C4—C5	176.4 (5)	O7—N4—C18—C19	177.1 (5)
O4—N2—C4—C5	−4.7 (7)	O8—N4—C18—C19	−1.9 (6)
O3—N2—C4—C3	−1.5 (7)	O7—N4—C18—C17	−4.9 (7)
O4—N2—C4—C3	177.4 (5)	O8—N4—C18—C17	176.2 (5)
C3—C4—C5—C6	−2.0 (7)	C17—C18—C19—C20	1.1 (7)
N2—C4—C5—C6	−179.8 (4)	N4—C18—C19—C20	179.1 (4)
C2—C1—C6—C5	1.1 (6)	C16—C15—C20—C19	0.3 (6)
S1—C1—C6—C5	−179.0 (3)	S2—C15—C20—C19	−177.1 (3)
C4—C5—C6—C1	0.3 (6)	C18—C19—C20—C15	−0.7 (6)
S1—N1—C7—C12	−71.1 (5)	S2—N3—C21—C22	−72.3 (5)
S1—N1—C7—C8	112.5 (4)	S2—N3—C21—C26	109.8 (4)
C12—C7—C8—C9	0.2 (6)	C26—C21—C22—C23	1.0 (6)
N1—C7—C8—C9	176.6 (4)	N3—C21—C22—C23	−176.9 (3)
C7—C8—C9—C10	1.2 (6)	C21—C22—C23—C24	0.9 (5)
C7—C8—C9—C13	−178.9 (4)	C21—C22—C23—C27	−179.5 (4)
C8—C9—C10—C11	−0.4 (7)	C22—C23—C24—C25	−2.0 (6)
C13—C9—C10—C11	179.6 (4)	C27—C23—C24—C25	178.4 (4)
C9—C10—C11—C12	−1.6 (7)	C23—C24—C25—C26	1.1 (7)
C9—C10—C11—C14	−179.0 (5)	C23—C24—C25—C28	−179.7 (4)
C8—C7—C12—C11	−2.3 (6)	C24—C25—C26—C21	0.9 (6)
N1—C7—C12—C11	−178.7 (3)	C28—C25—C26—C21	−178.3 (4)
C10—C11—C12—C7	3.0 (6)	C22—C21—C26—C25	−1.9 (6)
C14—C11—C12—C7	−179.7 (4)	N3—C21—C26—C25	176.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.85 (2)	2.35 (2)	3.129 (5)	152 (3)
N3—H3N···O8ii	0.84 (2)	2.40 (2)	3.168 (5)	152 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.85 (2)	2.35 (2)	3.129 (5)	152 (3)
N3—H3N⋯O8ii	0.84 (2)	2.40 (2)	3.168 (5)	152 (3)

Symmetry codes: (i) ; (ii) .