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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1991.
Published online 2009 July 25. doi:  10.1107/S1600536809028475
PMCID: PMC2977211

N′-(4-Bromo­phenyl­sulfon­yl)isonicotino­hydrazide

Abstract

The title compound, C12H10BrN3O3S, crystallizes with two crystallographically independent mol­ecules in the asymmetric unit. The dihedral angles between the two six-membered rings in the mol­ecules are 34.1 (3) and 45.1 (2)°. In the crystal structure, mol­ecules are connected via N—H(...)O and N—H(...)N hydrogen bonding.

Related literature

For general background to isonicotinic acid hydrazides, see: Carlton (1967 [triangle]). For a related structure, see: Wang et al. (2008 [triangle]). For the synthesis and biological activity of isoniazid and hydrazide derivatives, see: Lourenco et al. (2008 [triangle]); Kucukguzel et al. (2003 [triangle]); Carvalho et al. (2008 [triangle]), For graph-set notation, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1991-scheme1.jpg

Experimental

Crystal data

  • C12H10BrN3O3S
  • M r = 356.20
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1991-efi1.jpg
  • a = 10.1229 (6) Å
  • b = 19.0440 (12) Å
  • c = 15.0640 (7) Å
  • β = 96.862 (2)°
  • V = 2883.2 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 3.01 mm−1
  • T = 296 K
  • 0.36 × 0.30 × 0.15 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2007 [triangle]) T min = 0.349, T max = 0.641
  • 29398 measured reflections
  • 6601 independent reflections
  • 3473 reflections with I > 2σ(I)
  • R int = 0.053

Refinement

  • R[F 2 > 2σ(F 2)] = 0.053
  • wR(F 2) = 0.146
  • S = 1.01
  • 6601 reflections
  • 373 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 1.06 e Å−3
  • Δρmin = −0.88 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028475/nc2151sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028475/nc2151Isup2.hkl

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

Acknowledgments

The authors acknowledge the Higher Education Commission of Pakistan for providing a grant for the project of strengthening the Materials Chemistry Laboratory at GC University, Lahore, Pakistan.

supplementary crystallographic information

Comment

Isonicotinic acid hydrazide(INH) commonly known as isoniazid is a drug being used for the treatment of tuberclosis (TB) for long time (Carlton, 1967). Different approaches have been made for the synthesis of biologically active derivatives of isoniazid (Lourenco et al., 2008), (Kucukguzel et al., 2007), (Carvalho, et al.. 2008) and their crystallographic studies (Wang et al., 2008). In this context we report the crystal structure of title compound (N'-[(4-bromophenyl)sulfonyl]pyridine-4-carbohydrazide) a sulfonamide derivative of Isoniazid.

The title compound crystallizes with two crystallographically independent molecules in the asymmetric unit. The dihedral angle in each of these molecules amount to 34.1 (3) ° in molecule A, while it is 45.1 (2) ° (Fig. 1).

In the crystal structure the molecules are connected via intermolecular and intramolecular N–H···O and N–H···N hydrogen bonding (Fig. 2 and Tab. 1). One of the two indpenendent molecules is connected into dimers via N–H···O hydrogen bonding of the sulfonamide group into R22(8) rings (Bernstein et al., 1995). These dimers are further linked by additional N–H···O and N–H···N hydrogen bonding.

Experimental

To the solution of Isoniazid (0.5 g, 3.646 mmol) in distilled water (10 ml), 4-Bromobenzenesulfonyl chloride(0.9316 g, 3.65 mmol) was suspended. The reaction mixture was stirred at room temperature for 4 hrs at constant pH 8–9, which was adjusted by 1M sodium carbonate solution. After completion of the reaction which was observed by the consumption of suspended 4-Bromobenzenesulfonyl chloride, the pH was adjusted at 2–3 using 1 N HCl solution, which results the formation of a light yellow coloured precipitate, which was filtered off and dried. The prodcut was recrystallized from methanol.

Refinement

The C-H H-atoms were positioned with idealized geometry with C—H = 0.93 Å and were refined using a riding model with Uiso(H) = 1.2 Ueq(C). The N-H H atoms were located in difference map and refined isotropic ( Uiso(H) = 1.2 Ueq(N) with varying coordinates.

Figures

Fig. 1.
The structure of (I) with labeling and displacement ellipsoids drawn at the 50% probability level.
Fig. 2.
Unit cell packing for (I) with hydrogen bonding shown as dashed lines.

Crystal data

C12H10BrN3O3SF(000) = 1424
Mr = 356.20Dx = 1.641 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5184 reflections
a = 10.1229 (6) Åθ = 2.1–22.9°
b = 19.0440 (12) ŵ = 3.01 mm1
c = 15.0640 (7) ÅT = 296 K
β = 96.862 (2)°Needle, white yellow
V = 2883.2 (3) Å30.36 × 0.30 × 0.15 mm
Z = 8

Data collection

Bruker Kappa APEXII CCD diffractometer6601 independent reflections
Radiation source: fine-focus sealed tube3473 reflections with I > 2σ(I)
graphiteRint = 0.053
[var phi] and ω scansθmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)h = −13→11
Tmin = 0.349, Tmax = 0.641k = −24→23
29398 measured reflectionsl = −17→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.0597P)2 + 2.5287P] where P = (Fo2 + 2Fc2)/3
6601 reflections(Δ/σ)max = 0.001
373 parametersΔρmax = 1.06 e Å3
0 restraintsΔρmin = −0.88 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Br10.01531 (7)0.40221 (5)0.59324 (5)0.1083 (3)
Br21.07622 (6)0.14607 (4)0.37352 (6)0.1046 (3)
S10.46424 (10)0.38694 (6)0.33172 (7)0.0392 (3)
S20.46755 (9)0.10499 (5)0.43498 (6)0.0328 (2)
O10.1616 (3)0.49151 (15)0.28196 (19)0.0467 (7)
O20.4756 (3)0.31692 (15)0.2999 (2)0.0510 (8)
O30.5802 (3)0.42527 (17)0.3664 (2)0.0566 (9)
O40.2996 (2)0.20910 (13)0.59686 (17)0.0376 (7)
O50.3909 (3)0.16199 (14)0.39574 (18)0.0420 (7)
O60.4282 (3)0.03415 (14)0.41370 (17)0.0413 (7)
N1−0.2166 (3)0.3447 (2)0.1433 (3)0.0533 (10)
N20.2699 (3)0.41007 (18)0.2107 (2)0.0340 (8)
H20.270 (4)0.383 (2)0.174 (3)0.041*
N30.3969 (3)0.43457 (18)0.2456 (2)0.0353 (8)
H30.398 (4)0.474 (2)0.259 (3)0.042*
N40.5582 (4)0.42464 (18)0.6902 (2)0.0474 (9)
N50.5095 (3)0.17527 (17)0.5802 (2)0.0327 (8)
H50.590 (4)0.176 (2)0.600 (3)0.039*
N60.4645 (3)0.11035 (17)0.5443 (2)0.0336 (8)
H60.493 (4)0.077 (2)0.577 (3)0.040*
C10.0288 (4)0.4054 (2)0.1991 (3)0.0352 (9)
C20.0182 (4)0.3454 (3)0.1500 (4)0.0685 (16)
H2A0.09420.32350.13420.082*
C3−0.1055 (5)0.3172 (3)0.1236 (4)0.0732 (17)
H3A−0.11020.27610.09000.088*
C4−0.2061 (5)0.4033 (3)0.1895 (4)0.0774 (18)
H4−0.28370.42440.20380.093*
C5−0.0851 (4)0.4357 (3)0.2184 (4)0.0668 (15)
H5A−0.08280.47750.25050.080*
C60.1592 (4)0.4400 (2)0.2344 (3)0.0351 (9)
C70.3474 (4)0.3869 (2)0.4092 (2)0.0368 (9)
C80.2620 (4)0.3310 (2)0.4126 (3)0.0453 (11)
H80.27130.29090.37860.054*
C90.1620 (5)0.3355 (3)0.4677 (3)0.0574 (13)
H90.10310.29840.47110.069*
C100.1508 (5)0.3954 (3)0.5172 (3)0.0559 (13)
C110.2374 (5)0.4504 (3)0.5151 (3)0.0557 (13)
H110.22910.48990.55040.067*
C120.3362 (4)0.4468 (2)0.4607 (3)0.0460 (11)
H120.39530.48400.45810.055*
C130.4719 (4)0.29175 (19)0.6327 (2)0.0301 (8)
C140.5961 (4)0.3167 (2)0.6178 (3)0.0482 (11)
H140.65260.28940.58770.058*
C150.6342 (5)0.3825 (2)0.6483 (3)0.0556 (12)
H150.71830.39840.63900.067*
C160.4389 (4)0.4011 (2)0.7026 (3)0.0424 (10)
H160.38320.43050.73060.051*
C170.3926 (4)0.3353 (2)0.6764 (2)0.0363 (9)
H170.30890.32050.68810.044*
C180.4181 (4)0.22155 (19)0.6023 (2)0.0288 (8)
C190.6340 (4)0.1167 (2)0.4150 (2)0.0346 (9)
C200.6736 (4)0.1792 (3)0.3808 (3)0.0514 (11)
H200.61250.21510.36690.062*
C210.8050 (5)0.1878 (3)0.3674 (3)0.0654 (14)
H210.83300.22980.34430.078*
C220.8945 (5)0.1344 (3)0.3881 (3)0.0606 (14)
C230.8545 (5)0.0717 (3)0.4216 (3)0.0581 (13)
H230.91580.03570.43500.070*
C240.7237 (4)0.0623 (2)0.4352 (3)0.0477 (11)
H240.69570.02010.45760.057*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0866 (5)0.1511 (8)0.0966 (5)0.0053 (5)0.0490 (4)−0.0107 (5)
Br20.0489 (3)0.1069 (6)0.1655 (7)−0.0228 (3)0.0441 (4)−0.0377 (5)
S10.0289 (5)0.0374 (6)0.0504 (6)0.0021 (4)0.0004 (4)−0.0027 (5)
S20.0309 (5)0.0262 (5)0.0410 (5)0.0004 (4)0.0034 (4)−0.0016 (4)
O10.0373 (16)0.0419 (19)0.0602 (18)0.0023 (13)0.0028 (14)−0.0199 (15)
O20.0537 (18)0.0331 (17)0.0663 (19)0.0106 (14)0.0074 (15)−0.0016 (15)
O30.0308 (16)0.064 (2)0.072 (2)−0.0041 (15)−0.0075 (14)−0.0053 (17)
O40.0277 (14)0.0306 (16)0.0552 (17)−0.0032 (12)0.0079 (12)0.0012 (13)
O50.0397 (16)0.0371 (17)0.0483 (16)0.0046 (13)0.0015 (13)0.0059 (13)
O60.0444 (16)0.0295 (17)0.0488 (16)−0.0045 (13)0.0005 (13)−0.0060 (13)
N10.0282 (19)0.061 (3)0.070 (3)−0.0053 (18)0.0023 (17)−0.004 (2)
N20.0266 (17)0.030 (2)0.045 (2)−0.0025 (14)0.0027 (15)−0.0088 (15)
N30.0266 (17)0.0263 (19)0.052 (2)−0.0036 (15)0.0010 (14)−0.0082 (17)
N40.047 (2)0.030 (2)0.062 (2)−0.0042 (17)−0.0051 (18)−0.0024 (18)
N50.0257 (16)0.0244 (19)0.047 (2)−0.0017 (14)0.0003 (14)−0.0068 (15)
N60.0396 (19)0.0233 (19)0.0373 (18)−0.0021 (15)0.0028 (14)0.0028 (15)
C10.029 (2)0.038 (2)0.038 (2)−0.0023 (17)0.0013 (16)−0.0056 (18)
C20.019 (2)0.076 (4)0.110 (4)0.002 (2)0.005 (2)−0.043 (3)
C30.039 (3)0.070 (4)0.109 (4)−0.003 (3)0.000 (3)−0.045 (3)
C40.030 (3)0.089 (5)0.115 (5)0.005 (3)0.016 (3)−0.032 (4)
C50.034 (3)0.067 (4)0.101 (4)−0.001 (2)0.013 (3)−0.039 (3)
C60.033 (2)0.029 (2)0.042 (2)0.0000 (18)0.0043 (18)0.0011 (19)
C70.036 (2)0.032 (2)0.040 (2)0.0027 (18)−0.0041 (17)0.0008 (19)
C80.050 (3)0.035 (3)0.050 (3)−0.001 (2)0.004 (2)−0.003 (2)
C90.054 (3)0.054 (3)0.064 (3)−0.014 (2)0.007 (2)0.007 (3)
C100.053 (3)0.068 (4)0.047 (3)0.010 (3)0.009 (2)0.002 (3)
C110.064 (3)0.056 (3)0.046 (3)0.010 (3)0.002 (2)−0.009 (2)
C120.050 (3)0.042 (3)0.044 (2)0.001 (2)−0.006 (2)−0.004 (2)
C130.0307 (19)0.025 (2)0.034 (2)−0.0031 (16)0.0013 (16)0.0014 (17)
C140.036 (2)0.031 (2)0.080 (3)0.0004 (19)0.017 (2)−0.007 (2)
C150.039 (2)0.036 (3)0.091 (4)−0.010 (2)0.009 (2)−0.004 (3)
C160.055 (3)0.032 (3)0.041 (2)0.007 (2)0.005 (2)−0.0044 (19)
C170.038 (2)0.031 (2)0.040 (2)−0.0023 (18)0.0058 (18)−0.0013 (18)
C180.029 (2)0.025 (2)0.031 (2)−0.0024 (16)0.0007 (16)0.0026 (16)
C190.034 (2)0.031 (2)0.040 (2)−0.0039 (18)0.0096 (17)−0.0066 (18)
C200.044 (3)0.048 (3)0.063 (3)−0.003 (2)0.008 (2)0.004 (2)
C210.059 (3)0.059 (4)0.081 (4)−0.021 (3)0.019 (3)−0.004 (3)
C220.037 (3)0.068 (4)0.079 (3)−0.008 (3)0.018 (2)−0.023 (3)
C230.043 (3)0.052 (3)0.081 (3)0.005 (2)0.011 (2)−0.017 (3)
C240.044 (3)0.033 (3)0.068 (3)−0.001 (2)0.015 (2)−0.001 (2)

Geometric parameters (Å, °)

Br1—C101.893 (5)C4—H40.9300
Br2—C221.891 (4)C5—H5A0.9300
S1—O21.426 (3)C7—C81.376 (6)
S1—O31.427 (3)C7—C121.392 (6)
S1—N31.661 (4)C8—C91.386 (6)
S1—C71.758 (4)C8—H80.9300
S2—O51.421 (3)C9—C101.375 (7)
S2—O61.432 (3)C9—H90.9300
S2—N61.654 (3)C10—C111.370 (7)
S2—C191.760 (4)C11—C121.369 (6)
O1—C61.213 (5)C11—H110.9300
O4—C181.216 (4)C12—H120.9300
N1—C31.306 (6)C13—C171.375 (5)
N1—C41.313 (6)C13—C141.387 (5)
N2—C61.343 (5)C13—C181.495 (5)
N2—N31.409 (4)C14—C151.375 (6)
N2—H20.75 (4)C14—H140.9300
N3—H30.77 (4)C15—H150.9300
N4—C151.322 (6)C16—C171.379 (5)
N4—C161.323 (5)C16—H160.9300
N5—C181.348 (5)C17—H170.9300
N5—N61.403 (4)C19—C201.375 (6)
N5—H50.83 (4)C19—C241.386 (6)
N6—H60.83 (4)C20—C211.379 (6)
C1—C51.351 (6)C20—H200.9300
C1—C21.359 (6)C21—C221.372 (7)
C1—C61.513 (5)C21—H210.9300
C2—C31.377 (6)C22—C231.376 (7)
C2—H2A0.9300C23—C241.376 (6)
C3—H3A0.9300C23—H230.9300
C4—C51.393 (7)C24—H240.9300
O2—S1—O3120.34 (19)C9—C8—H8120.6
O2—S1—N3106.87 (17)C10—C9—C8119.3 (4)
O3—S1—N3104.46 (18)C10—C9—H9120.3
O2—S1—C7108.10 (19)C8—C9—H9120.3
O3—S1—C7110.28 (19)C11—C10—C9121.9 (4)
N3—S1—C7105.78 (17)C11—C10—Br1118.2 (4)
O5—S2—O6120.20 (17)C9—C10—Br1119.9 (4)
O5—S2—N6107.03 (17)C12—C11—C10119.4 (4)
O6—S2—N6104.08 (17)C12—C11—H11120.3
O5—S2—C19108.57 (18)C10—C11—H11120.3
O6—S2—C19109.09 (18)C11—C12—C7119.3 (4)
N6—S2—C19107.09 (17)C11—C12—H12120.4
C3—N1—C4116.3 (4)C7—C12—H12120.4
C6—N2—N3120.9 (3)C17—C13—C14117.6 (4)
C6—N2—H2124 (3)C17—C13—C18118.3 (3)
N3—N2—H2115 (3)C14—C13—C18124.1 (3)
N2—N3—S1112.5 (3)C15—C14—C13118.7 (4)
N2—N3—H3114 (3)C15—C14—H14120.6
S1—N3—H3109 (3)C13—C14—H14120.6
C15—N4—C16117.0 (4)N4—C15—C14123.9 (4)
C18—N5—N6118.1 (3)N4—C15—H15118.1
C18—N5—H5125 (3)C14—C15—H15118.1
N6—N5—H5114 (3)N4—C16—C17123.5 (4)
N5—N6—S2113.2 (2)N4—C16—H16118.2
N5—N6—H6111 (3)C17—C16—H16118.2
S2—N6—H6120 (3)C13—C17—C16119.2 (4)
C5—C1—C2117.5 (4)C13—C17—H17120.4
C5—C1—C6118.0 (4)C16—C17—H17120.4
C2—C1—C6124.5 (4)O4—C18—N5123.8 (3)
C1—C2—C3119.7 (4)O4—C18—C13121.0 (3)
C1—C2—H2A120.2N5—C18—C13115.2 (3)
C3—C2—H2A120.2C20—C19—C24121.0 (4)
N1—C3—C2123.8 (5)C20—C19—S2120.1 (3)
N1—C3—H3A118.1C24—C19—S2118.9 (3)
C2—C3—H3A118.1C19—C20—C21119.2 (5)
N1—C4—C5123.6 (4)C19—C20—H20120.4
N1—C4—H4118.2C21—C20—H20120.4
C5—C4—H4118.2C22—C21—C20120.1 (5)
C1—C5—C4119.0 (5)C22—C21—H21120.0
C1—C5—H5A120.5C20—C21—H21120.0
C4—C5—H5A120.5C21—C22—C23120.7 (4)
O1—C6—N2122.8 (4)C21—C22—Br2120.8 (4)
O1—C6—C1121.0 (3)C23—C22—Br2118.5 (4)
N2—C6—C1116.2 (3)C24—C23—C22119.8 (5)
C8—C7—C12121.3 (4)C24—C23—H23120.1
C8—C7—S1120.1 (3)C22—C23—H23120.1
C12—C7—S1118.4 (3)C23—C24—C19119.2 (4)
C7—C8—C9118.8 (4)C23—C24—H24120.4
C7—C8—H8120.6C19—C24—H24120.4
C6—N2—N3—S197.7 (4)Br1—C10—C11—C12−180.0 (3)
O2—S1—N3—N260.2 (3)C10—C11—C12—C7−0.6 (6)
O3—S1—N3—N2−171.2 (3)C8—C7—C12—C11−0.7 (6)
C7—S1—N3—N2−54.8 (3)S1—C7—C12—C11173.8 (3)
C18—N5—N6—S2103.9 (3)C17—C13—C14—C151.0 (6)
O5—S2—N6—N5−55.9 (3)C18—C13—C14—C15179.4 (4)
O6—S2—N6—N5175.8 (2)C16—N4—C15—C14−0.1 (7)
C19—S2—N6—N560.3 (3)C13—C14—C15—N4−1.2 (7)
C5—C1—C2—C3−1.4 (8)C15—N4—C16—C171.7 (6)
C6—C1—C2—C3177.8 (5)C14—C13—C17—C160.4 (6)
C4—N1—C3—C21.2 (9)C18—C13—C17—C16−178.1 (3)
C1—C2—C3—N1−0.1 (10)N4—C16—C17—C13−1.8 (6)
C3—N1—C4—C5−0.8 (9)N6—N5—C18—O43.7 (5)
C2—C1—C5—C41.7 (8)N6—N5—C18—C13−175.0 (3)
C6—C1—C5—C4−177.5 (5)C17—C13—C18—O416.8 (5)
N1—C4—C5—C1−0.7 (9)C14—C13—C18—O4−161.5 (4)
N3—N2—C6—O14.6 (6)C17—C13—C18—N5−164.5 (3)
N3—N2—C6—C1−174.9 (3)C14—C13—C18—N517.2 (5)
C5—C1—C6—O13.2 (6)O5—S2—C19—C2010.3 (4)
C2—C1—C6—O1−176.0 (5)O6—S2—C19—C20143.0 (3)
C5—C1—C6—N2−177.3 (4)N6—S2—C19—C20−105.0 (4)
C2—C1—C6—N23.5 (6)O5—S2—C19—C24−170.3 (3)
O2—S1—C7—C8−16.3 (4)O6—S2—C19—C24−37.6 (4)
O3—S1—C7—C8−149.7 (3)N6—S2—C19—C2474.4 (4)
N3—S1—C7—C897.9 (3)C24—C19—C20—C21−0.7 (7)
O2—S1—C7—C12169.1 (3)S2—C19—C20—C21178.7 (4)
O3—S1—C7—C1235.7 (4)C19—C20—C21—C220.0 (7)
N3—S1—C7—C12−76.7 (3)C20—C21—C22—C230.6 (8)
C12—C7—C8—C91.1 (6)C20—C21—C22—Br2−178.2 (4)
S1—C7—C8—C9−173.4 (3)C21—C22—C23—C24−0.5 (8)
C7—C8—C9—C10−0.1 (7)Br2—C22—C23—C24178.3 (4)
C8—C9—C10—C11−1.2 (7)C22—C23—C24—C19−0.2 (7)
C8—C9—C10—Br1−179.7 (3)C20—C19—C24—C230.8 (6)
C9—C10—C11—C121.6 (7)S2—C19—C24—C23−178.6 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···O4i0.76 (4)2.15 (4)2.882 (4)165.09
N3—H3···N4ii0.78 (4)2.10 (4)2.868 (5)168.21
N6—H6···O6iii0.83 (4)2.26 (4)2.998 (4)147.35
N5—H5···N1iv0.83 (4)2.03 (4)2.847 (4)168.32
N3—H3···O10.78 (4)2.49 (4)2.732 (4)100 (3)

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z+1; (iv) x+1, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2151).

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