Ethyl (3E)-3-[2-(4-bromo-phenyl-sulfon-yl)hydrazin-1-yl-idene]butano-ate.

The asymmetric unit of title compound, C(12)H(15)BrN(2)O(4)S, contains two mol-ecules (A and B), with slightly different conformations: the bromo-phenyl rings and the SO(2) planes of the sulfonyl groups are oriented at dihedral angles of 50.2 (2) (mol-ecule A) and 58.24 (7)° (mol-ecule B), and the ethyl acetate groups make dihedral angles of 63.99 (19)° (A) and 65.35 (16)° (B) with their bromo-phenyl groups. In the crystal, both mol-ecules exist as inversion dimers linked by pairs of N-H⋯O hydrogen bonds, which generate R(2) (2)(14) loops. The dimers are linked by C-H⋯O inter-actions.

Related literature

For a related structure, see: Uramoto et al. (1971 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C12H15BrN2O4S

M = 363.23

Triclinic,

a = 11.0550 (3) Å

b = 11.9763 (4) Å

c = 13.1146 (3) Å

α = 77.457 (1)°

β = 72.163 (2)°

γ = 73.981 (1)°

V = 1571.92 (8) Å3

Z = 4

Mo Kα radiation

μ = 2.76 mm−1

T = 296 K

0.30 × 0.15 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.635, T max = 0.650

22120 measured reflections

6096 independent reflections

4293 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.135

S = 1.05

6096 reflections

344 parameters

H-atom parameters constrained

Δρmax = 1.27 e Å−3

Δρmin = −1.11 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812019265/hb6771sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019265/hb6771Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812019265/hb6771Isup3.cml

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

C12H15BrN2O4S	Z = 4
Mr = 363.23	F(000) = 736
Triclinic, P1	Dx = 1.535 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.0550 (3) Å	Cell parameters from 4293 reflections
b = 11.9763 (4) Å	θ = 2.0–26.0°
c = 13.1146 (3) Å	µ = 2.76 mm−1
α = 77.457 (1)°	T = 296 K
β = 72.163 (2)°	Prism, colourless
γ = 73.981 (1)°	0.30 × 0.15 × 0.14 mm
V = 1571.92 (8) Å3

Bruker Kappa APEXII CCD diffractometer	6096 independent reflections
Radiation source: fine-focus sealed tube	4293 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 7.80 pixels mm-1	θmax = 26.0°, θmin = 2.0°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −14→14
Tmin = 0.635, Tmax = 0.650	l = −16→16
22120 measured reflections

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) = 0.135	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0612P)2 + 1.5738P] where P = (Fo2 + 2Fc2)/3
6096 reflections	(Δ/σ)max = 0.001
344 parameters	Δρmax = 1.27 e Å−3
0 restraints	Δρmin = −1.11 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Br1	1.11769 (5)	−0.38812 (5)	0.43815 (4)	0.0788 (2)
S1	0.78563 (9)	0.03587 (8)	0.17990 (7)	0.0411 (3)
O1	0.8641 (3)	0.1199 (2)	0.1313 (2)	0.0557 (10)
O2	0.7263 (3)	−0.0035 (3)	0.1162 (2)	0.0558 (10)
O3	0.5216 (3)	0.0584 (3)	0.6384 (2)	0.0629 (11)
O4	0.6201 (3)	0.1478 (3)	0.7100 (2)	0.0532 (10)
N1	0.6630 (3)	0.0928 (3)	0.2748 (2)	0.0397 (10)
N2	0.7025 (3)	0.1166 (3)	0.3597 (2)	0.0384 (10)
C1	0.8795 (3)	−0.0857 (3)	0.2460 (3)	0.0381 (11)
C2	1.0045 (4)	−0.0849 (4)	0.2421 (4)	0.0544 (14)
C3	1.0752 (4)	−0.1770 (4)	0.2979 (4)	0.0597 (16)
C4	1.0203 (4)	−0.2686 (3)	0.3560 (3)	0.0461 (12)
C5	0.8954 (4)	−0.2710 (4)	0.3593 (3)	0.0482 (12)
C6	0.8250 (4)	−0.1790 (3)	0.3030 (3)	0.0453 (12)
C7	0.6106 (3)	0.1691 (3)	0.4305 (3)	0.0396 (11)
C8	0.4704 (4)	0.2101 (4)	0.4284 (3)	0.0586 (16)
C9	0.6502 (4)	0.1910 (3)	0.5228 (3)	0.0424 (12)
C10	0.5890 (3)	0.1252 (3)	0.6290 (3)	0.0419 (12)
C11	0.5598 (6)	0.0940 (7)	0.8188 (4)	0.099 (3)
C12	0.6102 (3)	0.1162 (2)	0.89744 (13)	0.109 (3)
Br2	0.35796 (4)	0.36766 (4)	0.06489 (4)	0.0807 (2)
S2	0.68585 (4)	0.53305 (5)	0.30636 (4)	0.0406 (3)
O5	0.60925 (4)	0.63906 (5)	0.34696 (4)	0.0562 (10)
O6	0.73411 (5)	0.43392 (7)	0.37752 (5)	0.0600 (10)
O7	0.99883 (6)	0.64595 (9)	−0.14623 (7)	0.0629 (11)
O8	0.89569 (5)	0.82270 (6)	−0.20911 (5)	0.0571 (10)
N3	0.81726 (5)	0.56299 (7)	0.21809 (5)	0.0401 (10)
N4	0.7935 (3)	0.6522 (3)	0.1321 (2)	0.0384 (9)
C13	0.5960 (3)	0.4894 (3)	0.2375 (3)	0.0378 (11)
C14	0.4690 (4)	0.5485 (4)	0.2418 (4)	0.0541 (16)
C15	0.3982 (4)	0.5113 (4)	0.1912 (4)	0.0646 (16)
C16	0.4555 (4)	0.4169 (4)	0.1368 (3)	0.0513 (14)
C17	0.5823 (4)	0.3571 (3)	0.1316 (3)	0.0498 (14)
C18	0.6528 (4)	0.3938 (3)	0.1828 (3)	0.0448 (12)
C19	0.8945 (4)	0.6858 (3)	0.0688 (3)	0.0411 (12)
C20	1.0308 (4)	0.6400 (4)	0.0792 (4)	0.0603 (16)
C21	0.8693 (4)	0.7805 (3)	−0.0225 (3)	0.0442 (12)
C22	0.9295 (4)	0.7404 (3)	−0.1316 (3)	0.0428 (12)
C23	0.9492 (6)	0.7938 (5)	−0.3193 (4)	0.088 (2)
C24	0.8877 (10)	0.8834 (7)	−0.3902 (5)	0.151 (4)
H1	0.58287	0.10678	0.27334	0.0476*
H2	1.04121	−0.02258	0.20198	0.0649*
H3	1.15997	−0.17705	0.29617	0.0714*
H5	0.85930	−0.33381	0.39886	0.0579*
H6	0.74091	−0.17969	0.30335	0.0542*
H8A	0.46525	0.24267	0.35579	0.0878*
H8B	0.42710	0.26895	0.47500	0.0878*
H8C	0.42897	0.14484	0.45306	0.0878*
H9A	0.62468	0.27440	0.52727	0.0511*
H9B	0.74440	0.16716	0.50890	0.0511*
H11A	0.46620	0.12524	0.83593	0.1181*
H11B	0.57574	0.00993	0.82031	0.1181*
H12A	0.70237	0.08301	0.88193	0.1631*
H12B	0.56803	0.08127	0.96785	0.1631*
H12C	0.59457	0.19941	0.89594	0.1631*
H3A	0.89452	0.52737	0.22352	0.0481*
H14	0.43149	0.61308	0.27857	0.0650*
H15	0.31208	0.54993	0.19406	0.0775*
H17	0.61965	0.29300	0.09419	0.0597*
H18	0.73855	0.35439	0.18051	0.0534*
H20A	1.03026	0.62775	0.15418	0.0903*
H20B	1.08237	0.69588	0.03942	0.0903*
H20C	1.06744	0.56699	0.05082	0.0903*
H21A	0.90367	0.84604	−0.02061	0.0530*
H21B	0.77582	0.80815	−0.01255	0.0530*
H23A	1.04258	0.78818	−0.34174	0.1054*
H23B	0.93377	0.71873	−0.32190	0.1054*
H24A	0.79493	0.89168	−0.36510	0.2268*
H24B	0.91809	0.86258	−0.46188	0.2268*
H24C	0.90870	0.95638	−0.39131	0.2268*

	U11	U22	U33	U12	U13	U23
Br1	0.0633 (3)	0.0840 (4)	0.0816 (4)	−0.0112 (3)	−0.0321 (3)	0.0156 (3)
S1	0.0424 (5)	0.0425 (5)	0.0351 (5)	−0.0108 (4)	−0.0027 (4)	−0.0082 (4)
O1	0.0520 (17)	0.0497 (17)	0.0538 (17)	−0.0190 (14)	0.0037 (13)	0.0009 (13)
O2	0.0610 (18)	0.0643 (19)	0.0442 (16)	−0.0064 (14)	−0.0166 (14)	−0.0179 (14)
O3	0.076 (2)	0.073 (2)	0.0516 (17)	−0.0494 (18)	−0.0108 (15)	−0.0003 (15)
O4	0.0545 (16)	0.075 (2)	0.0368 (14)	−0.0327 (15)	−0.0092 (12)	−0.0028 (13)
N1	0.0329 (16)	0.0461 (18)	0.0392 (17)	−0.0084 (14)	−0.0044 (13)	−0.0123 (14)
N2	0.0397 (17)	0.0412 (17)	0.0361 (16)	−0.0136 (14)	−0.0071 (14)	−0.0077 (14)
C1	0.039 (2)	0.039 (2)	0.0376 (19)	−0.0126 (16)	−0.0050 (16)	−0.0109 (16)
C2	0.046 (2)	0.052 (2)	0.067 (3)	−0.023 (2)	−0.015 (2)	0.003 (2)
C3	0.042 (2)	0.068 (3)	0.073 (3)	−0.024 (2)	−0.018 (2)	0.001 (2)
C4	0.044 (2)	0.051 (2)	0.045 (2)	−0.0073 (18)	−0.0155 (18)	−0.0092 (19)
C5	0.050 (2)	0.049 (2)	0.049 (2)	−0.0175 (19)	−0.0138 (19)	−0.0045 (19)
C6	0.039 (2)	0.049 (2)	0.053 (2)	−0.0160 (18)	−0.0125 (18)	−0.0092 (19)
C7	0.041 (2)	0.040 (2)	0.0349 (19)	−0.0133 (16)	−0.0021 (17)	−0.0056 (16)
C8	0.044 (2)	0.074 (3)	0.052 (3)	0.000 (2)	−0.008 (2)	−0.021 (2)
C9	0.045 (2)	0.046 (2)	0.038 (2)	−0.0197 (18)	−0.0028 (17)	−0.0095 (17)
C10	0.038 (2)	0.046 (2)	0.043 (2)	−0.0148 (18)	−0.0075 (17)	−0.0068 (18)
C11	0.107 (4)	0.164 (6)	0.040 (3)	−0.084 (4)	−0.012 (3)	0.012 (3)
C12	0.137 (6)	0.154 (6)	0.052 (3)	−0.068 (5)	−0.029 (4)	0.002 (4)
Br2	0.0752 (4)	0.0956 (4)	0.0968 (4)	−0.0393 (3)	−0.0383 (3)	−0.0181 (3)
S2	0.0412 (5)	0.0483 (6)	0.0339 (5)	−0.0158 (4)	−0.0065 (4)	−0.0066 (4)
O5	0.0492 (16)	0.0646 (19)	0.0545 (17)	−0.0135 (14)	0.0028 (14)	−0.0311 (15)
O6	0.0692 (19)	0.0684 (19)	0.0463 (16)	−0.0249 (16)	−0.0256 (14)	0.0111 (14)
O7	0.069 (2)	0.0466 (18)	0.0585 (18)	0.0060 (15)	−0.0043 (16)	−0.0199 (15)
O8	0.0664 (19)	0.0519 (17)	0.0427 (16)	−0.0043 (14)	−0.0066 (14)	−0.0082 (14)
N3	0.0303 (16)	0.0441 (18)	0.0438 (18)	−0.0091 (13)	−0.0073 (13)	−0.0044 (14)
N4	0.0411 (17)	0.0359 (16)	0.0374 (16)	−0.0107 (14)	−0.0044 (14)	−0.0095 (13)
C13	0.038 (2)	0.040 (2)	0.0370 (19)	−0.0138 (16)	−0.0103 (16)	−0.0019 (16)
C14	0.040 (2)	0.054 (3)	0.069 (3)	−0.0041 (19)	−0.012 (2)	−0.022 (2)
C15	0.038 (2)	0.076 (3)	0.084 (3)	−0.006 (2)	−0.021 (2)	−0.022 (3)
C16	0.051 (2)	0.059 (3)	0.054 (2)	−0.025 (2)	−0.020 (2)	−0.004 (2)
C17	0.056 (3)	0.043 (2)	0.055 (2)	−0.0112 (19)	−0.018 (2)	−0.0119 (19)
C18	0.041 (2)	0.042 (2)	0.051 (2)	−0.0057 (17)	−0.0147 (18)	−0.0069 (18)
C19	0.042 (2)	0.042 (2)	0.040 (2)	−0.0139 (17)	−0.0009 (17)	−0.0161 (17)
C20	0.039 (2)	0.078 (3)	0.063 (3)	−0.021 (2)	−0.008 (2)	−0.006 (2)
C21	0.049 (2)	0.038 (2)	0.041 (2)	−0.0146 (17)	0.0016 (18)	−0.0097 (17)
C22	0.039 (2)	0.042 (2)	0.045 (2)	−0.0122 (18)	−0.0008 (17)	−0.0120 (18)
C23	0.105 (4)	0.096 (4)	0.045 (3)	0.001 (3)	−0.009 (3)	−0.021 (3)
C24	0.223 (10)	0.125 (6)	0.077 (4)	0.040 (6)	−0.060 (6)	−0.027 (4)

Br1—C4	1.887 (4)	C6—H6	0.9300
Br2—C16	1.901 (5)	C8—H8B	0.9600
S1—O2	1.424 (3)	C8—H8A	0.9600
S1—N1	1.636 (3)	C8—H8C	0.9600
S1—O1	1.427 (3)	C9—H9B	0.9700
S1—C1	1.766 (4)	C9—H9A	0.9700
S2—O6	1.4280 (9)	C11—H11B	0.9700
S2—N3	1.6297 (8)	C11—H11A	0.9700
S2—C13	1.765 (4)	C12—H12A	0.9600
S2—O5	1.4271 (8)	C12—H12B	0.9600
O3—C10	1.200 (5)	C12—H12C	0.9600
O4—C11	1.467 (6)	C13—C18	1.380 (5)
O4—C10	1.311 (5)	C13—C14	1.377 (6)
O7—C22	1.196 (4)	C14—C15	1.375 (7)
O8—C23	1.462 (5)	C15—C16	1.366 (6)
O8—C22	1.319 (4)	C16—C17	1.375 (6)
N1—N2	1.420 (4)	C17—C18	1.375 (6)
N2—C7	1.270 (5)	C19—C20	1.492 (7)
N1—H1	0.8600	C19—C21	1.496 (5)
N3—N4	1.409 (3)	C21—C22	1.503 (5)
N4—C19	1.278 (5)	C23—C24	1.425 (10)
N3—H3A	0.8600	C14—H14	0.9300
C1—C2	1.370 (6)	C15—H15	0.9300
C1—C6	1.380 (5)	C17—H17	0.9300
C2—C3	1.374 (7)	C18—H18	0.9300
C3—C4	1.369 (6)	C20—H20A	0.9600
C4—C5	1.376 (7)	C20—H20B	0.9600
C5—C6	1.375 (6)	C20—H20C	0.9600
C7—C9	1.501 (5)	C21—H21A	0.9700
C7—C8	1.498 (6)	C21—H21B	0.9700
C9—C10	1.503 (5)	C23—H23A	0.9700
C11—C12	1.413 (7)	C23—H23B	0.9700
C2—H2	0.9300	C24—H24A	0.9600
C3—H3	0.9300	C24—H24B	0.9600
C5—H5	0.9300	C24—H24C	0.9600
O1—S1—O2	120.04 (17)	O4—C11—H11B	109.00
O1—S1—N1	108.05 (17)	C12—C11—H11A	109.00
O1—S1—C1	107.54 (18)	H11A—C11—H11B	108.00
O2—S1—N1	104.25 (19)	O4—C11—H11A	109.00
O2—S1—C1	109.86 (19)	C12—C11—H11B	109.00
N1—S1—C1	106.29 (17)	C11—C12—H12B	109.00
O5—S2—O6	120.45 (5)	H12A—C12—H12C	109.00
O5—S2—N3	107.69 (5)	H12B—C12—H12C	109.00
O5—S2—C13	107.71 (12)	C11—C12—H12A	109.00
O6—S2—N3	103.84 (5)	C11—C12—H12C	110.00
O6—S2—C13	108.70 (12)	H12A—C12—H12B	109.00
N3—S2—C13	107.84 (13)	C14—C13—C18	120.7 (4)
C10—O4—C11	116.9 (4)	S2—C13—C14	119.8 (3)
C22—O8—C23	116.2 (3)	S2—C13—C18	119.4 (3)
S1—N1—N2	113.1 (3)	C13—C14—C15	119.4 (4)
N1—N2—C7	114.7 (3)	C14—C15—C16	119.4 (4)
S1—N1—H1	123.00	Br2—C16—C17	119.0 (3)
N2—N1—H1	124.00	C15—C16—C17	121.9 (4)
S2—N3—N4	114.28 (15)	Br2—C16—C15	119.2 (4)
N3—N4—C19	115.1 (3)	C16—C17—C18	118.7 (4)
S2—N3—H3A	123.00	C13—C18—C17	119.8 (4)
N4—N3—H3A	123.00	N4—C19—C20	126.0 (4)
C2—C1—C6	120.9 (4)	C20—C19—C21	118.9 (4)
S1—C1—C6	119.6 (3)	N4—C19—C21	115.1 (4)
S1—C1—C2	119.5 (3)	C19—C21—C22	113.0 (3)
C1—C2—C3	119.4 (4)	O7—C22—O8	124.3 (3)
C2—C3—C4	119.7 (4)	O7—C22—C21	124.4 (3)
C3—C4—C5	121.4 (4)	O8—C22—C21	111.3 (3)
Br1—C4—C5	120.7 (3)	O8—C23—C24	108.9 (5)
Br1—C4—C3	117.9 (4)	C13—C14—H14	120.00
C4—C5—C6	118.9 (4)	C15—C14—H14	120.00
C1—C6—C5	119.8 (4)	C14—C15—H15	120.00
C8—C7—C9	118.9 (3)	C16—C15—H15	120.00
N2—C7—C9	115.2 (3)	C16—C17—H17	121.00
N2—C7—C8	125.9 (3)	C18—C17—H17	121.00
C7—C9—C10	112.1 (3)	C13—C18—H18	120.00
O4—C10—C9	111.9 (3)	C17—C18—H18	120.00
O3—C10—C9	124.1 (3)	C19—C20—H20A	109.00
O3—C10—O4	124.0 (3)	C19—C20—H20B	109.00
O4—C11—C12	111.3 (5)	C19—C20—H20C	109.00
C3—C2—H2	120.00	H20A—C20—H20B	109.00
C1—C2—H2	120.00	H20A—C20—H20C	109.00
C4—C3—H3	120.00	H20B—C20—H20C	110.00
C2—C3—H3	120.00	C19—C21—H21A	109.00
C6—C5—H5	121.00	C19—C21—H21B	109.00
C4—C5—H5	121.00	C22—C21—H21A	109.00
C5—C6—H6	120.00	C22—C21—H21B	109.00
C1—C6—H6	120.00	H21A—C21—H21B	108.00
C7—C8—H8C	109.00	O8—C23—H23A	110.00
H8B—C8—H8C	109.00	O8—C23—H23B	110.00
H8A—C8—H8C	109.00	C24—C23—H23A	110.00
C7—C8—H8B	109.00	C24—C23—H23B	110.00
C7—C8—H8A	110.00	H23A—C23—H23B	108.00
H8A—C8—H8B	109.00	C23—C24—H24A	109.00
C7—C9—H9A	109.00	C23—C24—H24B	109.00
C10—C9—H9B	109.00	C23—C24—H24C	109.00
C10—C9—H9A	109.00	H24A—C24—H24B	110.00
C7—C9—H9B	109.00	H24A—C24—H24C	109.00
H9A—C9—H9B	108.00	H24B—C24—H24C	109.00
O1—S1—N1—N2	−63.0 (3)	N3—N4—C19—C21	180.0 (3)
O2—S1—N1—N2	168.3 (3)	S1—C1—C2—C3	176.9 (4)
C1—S1—N1—N2	52.2 (3)	C6—C1—C2—C3	−1.6 (7)
O1—S1—C1—C2	−0.5 (4)	S1—C1—C6—C5	−176.6 (3)
O1—S1—C1—C6	178.0 (3)	C2—C1—C6—C5	1.9 (6)
O2—S1—C1—C2	131.8 (3)	C1—C2—C3—C4	0.4 (7)
O2—S1—C1—C6	−49.8 (4)	C2—C3—C4—Br1	−176.2 (4)
N1—S1—C1—C2	−116.0 (4)	C2—C3—C4—C5	0.4 (7)
N1—S1—C1—C6	62.5 (3)	Br1—C4—C5—C6	176.5 (3)
C13—S2—N3—N4	59.0 (2)	C3—C4—C5—C6	−0.1 (6)
O5—S2—C13—C14	−7.2 (4)	C4—C5—C6—C1	−1.0 (6)
O5—S2—C13—C18	174.8 (3)	N2—C7—C9—C10	−115.5 (4)
O6—S2—C13—C14	124.8 (3)	C8—C7—C9—C10	64.9 (4)
O6—S2—C13—C18	−53.1 (3)	C7—C9—C10—O3	3.5 (5)
O5—S2—N3—N4	−57.04 (16)	C7—C9—C10—O4	−177.7 (3)
O6—S2—N3—N4	174.17 (15)	S2—C13—C14—C15	−177.7 (4)
N3—S2—C13—C18	58.9 (3)	C18—C13—C14—C15	0.2 (7)
N3—S2—C13—C14	−123.2 (3)	S2—C13—C18—C17	178.1 (3)
C11—O4—C10—C9	176.5 (4)	C14—C13—C18—C17	0.2 (6)
C11—O4—C10—O3	−4.8 (6)	C13—C14—C15—C16	−0.5 (7)
C10—O4—C11—C12	174.6 (4)	C14—C15—C16—Br2	−178.9 (4)
C23—O8—C22—O7	−0.5 (6)	C14—C15—C16—C17	0.4 (7)
C22—O8—C23—C24	171.0 (6)	Br2—C16—C17—C18	179.4 (3)
C23—O8—C22—C21	179.7 (4)	C15—C16—C17—C18	0.0 (6)
S1—N1—N2—C7	174.9 (3)	C16—C17—C18—C13	−0.3 (6)
N1—N2—C7—C8	−2.5 (5)	N4—C19—C21—C22	−113.9 (4)
N1—N2—C7—C9	177.9 (3)	C20—C19—C21—C22	66.6 (5)
S2—N3—N4—C19	172.6 (2)	C19—C21—C22—O7	−5.4 (6)
N3—N4—C19—C20	−0.5 (5)	C19—C21—C22—O8	174.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.86	2.46	2.909 (5)	114
N3—H3A···O7ii	0.86	2.36	2.8855 (13)	120
C3—H3···O4iii	0.93	2.53	3.450 (6)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.86	2.46	2.909 (5)	114
N3—H3A⋯O7ii	0.86	2.36	2.8855 (13)	120
C3—H3⋯O4iii	0.93	2.53	3.450 (6)	172

Symmetry codes: (i) ; (ii) ; (iii) .