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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3062.
Published online 2010 November 6. doi:  10.1107/S1600536810044375
PMCID: PMC3011474

N-(2,3-Dichloro­phen­yl)-4-methyl­benzene­sulfonamide

Abstract

The title compound, C13H11Cl2NO2S, contains two molecules in the asymmetric unit in which the dihedral angles between the benzene rings are 76.0 (1) and 79.9 (1)°. The conformations of the N—H bonds with respect to their adjacent ortho-chlorine atoms are syn. In the crystal, N—H(...)O hydrogen bonds link the molecules into dimers.

Related literature

For our study of the effect of substituents on the structures of N-(ar­yl)aryl­sulfonamides, see: Gowda et al. (2009 [triangle], 2010a [triangle],b [triangle]). For related structures, see: Gelbrich et al. (2007 [triangle]); Perlovich et al. (2006 [triangle]).

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Object name is e-66-o3062-scheme1.jpg

Experimental

Crystal data

  • C13H11Cl2NO2S
  • M r = 316.19
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3062-efi1.jpg
  • a = 14.035 (3) Å
  • b = 12.386 (2) Å
  • c = 15.993 (3) Å
  • β = 98.30 (1)°
  • V = 2751.1 (9) Å3
  • Z = 8
  • Cu Kα radiation
  • μ = 5.64 mm−1
  • T = 299 K
  • 0.50 × 0.45 × 0.40 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • 9784 measured reflections
  • 4903 independent reflections
  • 4359 reflections with I > 2σ(I)
  • R int = 0.131
  • 3 standard reflections every 120 min intensity decay: 1.0%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.065
  • wR(F 2) = 0.176
  • S = 1.11
  • 4903 reflections
  • 352 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.81 e Å−3
  • Δρmin = −0.56 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 [triangle]); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810044375/bq2248sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044375/bq2248Isup2.hkl

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

Acknowledgments

KS thanks the University Grants Commission, Government of India, New Delhi for the award of a research fellowship under its faculty improvement program.

supplementary crystallographic information

Comment

As part of a study of the substituent effects on the crystal structures of N-(aryl)-arylsulfonamides (Gowda et al., 2009; 2010a, b), in the present work, the structure of 4-methyl-N-(2,3-dichlorophenyl)- benzenesulfonamide (I) has been determined. The asymmetric unit of (I) contains two independent molecules. In one of the molecules, conformation of the N—C bond in the C—SO2—NH—C segment of the structure has gauche torsions with respect to the S═O bonds (Fig. 1). The molecules are bent at the S atoms with the C—SO2—NH—C torsion angles of 65.4 (2) and -61.7 (2). The conformations of the N—H bonds and the ortho-chloro groups in the anilino benzene rings are syn to each other. The benzene rings in the title compound are tilted relative to each other by 76.0 (1)° (molecule 1) and 79.9 (1)° (molecule 2). The other bond parameters in (I) are similar to those observed in 4-methyl-N-(2-chlorophenyl)- benzenesulfonamide (Gowda et al., 2010a), 4-methyl-N-(3-chlorophenyl)benzenesulfonamide (Gowda et al., 2010b), 4-methyl-N-(3,5-dichlorophenyl)benzenesulfonamide (Gowda et al., 2009) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007). The N—H···O hydrogen bonds (Table 1) pack the molecules into infinite chains in the direction of a- axis (Fig. 2).

Experimental

The solution of toluene (10 ml) in chloroform (40 ml) was treated dropwise with chlorosulfonic acid (25 ml) at 0 ° C. After the initial evolution of hydrogen chloride subsided, the reaction mixture was brought to room temperature and poured into crushed ice in a beaker. The chloroform layer was separated, washed with cold water and allowed to evaporate slowly. The residual 4-methylbenzenesulfonylchloride was treated with 2,3-dichloroaniline in the stoichiometric ratio and boiled for ten minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant 4-methyl-N-(2,3-dichlorophenyl)benzenesulfonamide was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from dilute ethanol. The purity of the compound was checked and characterized by recording its infrared and NMR spectra. The single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.

Refinement

The H atoms of the NH groups were located in a difference map and later restrained to N—H = 0.86 (2) %A. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93–0.96 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).

Figures

Fig. 1.
Molecular structure of (I), showing the atom labeling scheme and displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Molecular packing of (I) with hydrogen bonding shown as dashed lines.

Crystal data

C13H11Cl2NO2SF(000) = 1296
Mr = 316.19Dx = 1.527 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 14.035 (3) Åθ = 5.6–19.2°
b = 12.386 (2) ŵ = 5.64 mm1
c = 15.993 (3) ÅT = 299 K
β = 98.30 (1)°Prism, colourless
V = 2751.1 (9) Å30.50 × 0.45 × 0.40 mm
Z = 8

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.131
Radiation source: fine-focus sealed tubeθmax = 67.0°, θmin = 3.9°
graphiteh = −16→16
ω/2θ scansk = −14→0
9784 measured reflectionsl = −19→19
4903 independent reflections3 standard reflections every 120 min
4359 reflections with I > 2σ(I) intensity decay: 1.0%

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.065H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.176w = 1/[σ2(Fo2) + (0.0914P)2 + 0.5192P] where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
4903 reflectionsΔρmax = 0.81 e Å3
352 parametersΔρmin = −0.56 e Å3
2 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0038 (4)

Special details

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.

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

xyzUiso*/Ueq
C10.88559 (18)0.0982 (2)0.42938 (14)0.0312 (6)
C20.9254 (2)0.0053 (2)0.40037 (17)0.0404 (6)
H20.8955−0.06120.40380.048*
C31.0094 (2)0.0132 (3)0.36653 (18)0.0473 (7)
H31.0361−0.04890.34680.057*
C41.05552 (19)0.1107 (3)0.36089 (16)0.0412 (7)
C51.0132 (2)0.2032 (3)0.38929 (19)0.0453 (7)
H51.04230.27000.38490.054*
C60.9292 (2)0.1972 (2)0.42354 (18)0.0413 (6)
H60.90200.25920.44270.050*
C70.66060 (17)0.0946 (2)0.32818 (17)0.0353 (6)
C80.64433 (18)0.1597 (2)0.25643 (17)0.0375 (6)
C90.6067 (2)0.1151 (3)0.17875 (18)0.0428 (7)
C100.5881 (2)0.0062 (3)0.1720 (2)0.0578 (9)
H100.5641−0.02370.11990.069*
C110.6048 (3)−0.0574 (3)0.2417 (3)0.0637 (10)
H110.5925−0.13110.23650.076*
C120.6398 (2)−0.0151 (3)0.3207 (2)0.0530 (8)
H120.6493−0.05970.36800.064*
C131.1486 (2)0.1179 (4)0.3250 (2)0.0625 (10)
H13A1.13540.13670.26620.075*
H13B1.18090.04950.33110.075*
H13C1.18880.17230.35480.075*
N10.69333 (16)0.1410 (2)0.40784 (15)0.0379 (5)
H1N0.700 (3)0.2081 (15)0.410 (2)0.045*
O10.75897 (16)−0.02137 (18)0.48773 (13)0.0491 (5)
O20.78830 (16)0.16207 (18)0.54657 (12)0.0470 (5)
Cl10.67147 (7)0.29473 (6)0.26491 (5)0.0542 (3)
Cl20.58337 (8)0.19562 (9)0.09061 (5)0.0690 (3)
S10.77998 (4)0.08962 (6)0.47581 (4)0.0344 (2)
C140.62488 (18)0.4300 (2)0.57233 (14)0.0302 (5)
C150.5861 (2)0.3271 (2)0.57427 (16)0.0372 (6)
H150.61730.26800.55480.045*
C160.5007 (2)0.3142 (2)0.60547 (18)0.0420 (6)
H160.47400.24550.60660.050*
C170.45287 (19)0.4019 (3)0.63566 (16)0.0397 (6)
C180.4933 (2)0.5035 (3)0.63213 (18)0.0437 (7)
H180.46190.56290.65100.052*
C190.5792 (2)0.5186 (2)0.60121 (17)0.0383 (6)
H190.60590.58720.59980.046*
C200.83949 (17)0.4415 (2)0.68958 (16)0.0322 (5)
C210.87507 (17)0.3732 (2)0.75535 (16)0.0318 (5)
C220.89966 (18)0.4133 (2)0.83721 (17)0.0375 (6)
C230.8875 (2)0.5210 (3)0.8543 (2)0.0484 (7)
H230.90370.54750.90890.058*
C240.8515 (2)0.5880 (3)0.7900 (2)0.0509 (7)
H240.84210.66050.80140.061*
C250.8284 (2)0.5505 (2)0.70714 (19)0.0440 (7)
H250.80560.59820.66390.053*
C260.3602 (2)0.3853 (3)0.6705 (2)0.0560 (9)
H26A0.37390.36970.72980.067*
H26B0.32570.32590.64180.067*
H26C0.32180.44950.66200.067*
N20.81882 (17)0.39956 (19)0.60644 (14)0.0370 (5)
H2N0.826 (2)0.3316 (16)0.603 (2)0.044*
O30.73700 (16)0.37678 (18)0.46284 (11)0.0475 (5)
O40.75082 (16)0.55963 (18)0.52425 (13)0.0480 (5)
Cl30.88652 (6)0.23746 (6)0.73614 (5)0.0526 (3)
Cl40.94255 (7)0.32756 (8)0.91866 (5)0.0600 (3)
S20.73465 (5)0.44706 (5)0.53342 (4)0.0342 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0288 (12)0.0371 (14)0.0268 (11)0.0076 (10)0.0013 (10)−0.0017 (10)
C20.0439 (15)0.0369 (14)0.0404 (13)0.0106 (12)0.0061 (12)−0.0029 (11)
C30.0477 (16)0.0519 (17)0.0430 (14)0.0209 (15)0.0094 (13)−0.0032 (13)
C40.0297 (13)0.0630 (19)0.0302 (12)0.0149 (13)0.0021 (10)0.0059 (12)
C50.0375 (15)0.0479 (16)0.0507 (16)0.0007 (13)0.0070 (13)0.0035 (13)
C60.0379 (14)0.0394 (15)0.0475 (14)0.0070 (12)0.0089 (12)−0.0044 (12)
C70.0203 (11)0.0388 (14)0.0458 (14)0.0026 (10)0.0010 (10)−0.0021 (11)
C80.0250 (11)0.0403 (14)0.0472 (14)0.0050 (11)0.0055 (11)−0.0079 (12)
C90.0314 (13)0.0523 (17)0.0436 (14)0.0073 (13)0.0021 (11)−0.0059 (13)
C100.0478 (17)0.056 (2)0.0638 (19)0.0036 (16)−0.0109 (16)−0.0218 (17)
C110.060 (2)0.0422 (17)0.080 (2)−0.0048 (16)−0.0183 (19)−0.0116 (17)
C120.0467 (17)0.0407 (16)0.067 (2)−0.0051 (14)−0.0069 (16)0.0032 (15)
C130.0407 (17)0.099 (3)0.0501 (17)0.0165 (18)0.0151 (14)0.0137 (19)
N10.0304 (11)0.0368 (12)0.0465 (12)0.0050 (10)0.0062 (10)−0.0011 (10)
O10.0523 (12)0.0440 (12)0.0517 (11)−0.0005 (10)0.0096 (10)0.0120 (9)
O20.0531 (12)0.0547 (12)0.0342 (9)0.0095 (10)0.0102 (9)−0.0046 (9)
Cl10.0739 (6)0.0381 (4)0.0496 (4)0.0011 (3)0.0049 (4)0.0001 (3)
Cl20.0888 (7)0.0725 (6)0.0424 (4)0.0130 (5)−0.0019 (4)0.0002 (4)
S10.0341 (4)0.0386 (4)0.0314 (3)0.0055 (3)0.0076 (3)0.0024 (2)
C140.0315 (12)0.0331 (12)0.0247 (10)0.0062 (10)−0.0002 (10)0.0018 (9)
C150.0435 (14)0.0300 (12)0.0386 (12)0.0062 (12)0.0076 (12)−0.0001 (11)
C160.0411 (15)0.0397 (15)0.0445 (14)−0.0033 (13)0.0034 (12)0.0034 (12)
C170.0295 (13)0.0564 (17)0.0308 (12)0.0052 (12)−0.0035 (10)0.0041 (12)
C180.0374 (14)0.0464 (16)0.0472 (15)0.0149 (13)0.0062 (12)−0.0023 (13)
C190.0418 (14)0.0304 (13)0.0410 (13)0.0066 (12)0.0005 (12)−0.0027 (11)
C200.0214 (11)0.0346 (13)0.0403 (13)−0.0015 (10)0.0036 (10)−0.0017 (11)
C210.0220 (11)0.0311 (12)0.0424 (13)0.0003 (10)0.0047 (10)−0.0023 (11)
C220.0259 (11)0.0449 (15)0.0406 (13)−0.0018 (11)0.0007 (10)0.0028 (12)
C230.0416 (15)0.0538 (18)0.0476 (15)−0.0032 (14)−0.0011 (13)−0.0150 (14)
C240.0511 (17)0.0367 (15)0.0613 (18)0.0000 (14)−0.0044 (15)−0.0127 (14)
C250.0441 (15)0.0334 (14)0.0509 (15)0.0025 (12)−0.0055 (13)0.0003 (12)
C260.0375 (15)0.083 (3)0.0479 (16)0.0029 (16)0.0082 (13)0.0082 (17)
N20.0370 (12)0.0364 (12)0.0379 (11)0.0087 (10)0.0061 (10)−0.0006 (9)
O30.0581 (13)0.0548 (12)0.0315 (9)0.0080 (11)0.0128 (9)−0.0008 (9)
O40.0569 (12)0.0404 (11)0.0480 (11)−0.0015 (10)0.0121 (10)0.0119 (9)
Cl30.0709 (5)0.0328 (4)0.0515 (4)0.0090 (3)0.0001 (4)0.0004 (3)
Cl40.0666 (5)0.0630 (5)0.0455 (4)0.0009 (4)−0.0081 (4)0.0085 (4)
S20.0375 (4)0.0354 (4)0.0306 (3)0.0034 (3)0.0077 (3)0.0043 (2)

Geometric parameters (Å, °)

C1—C61.380 (4)C14—C191.384 (4)
C1—C21.387 (4)C14—C151.388 (4)
C1—S11.754 (2)C14—S21.756 (2)
C2—C31.370 (4)C15—C161.373 (4)
C2—H20.9300C15—H150.9300
C3—C41.380 (5)C16—C171.399 (4)
C3—H30.9300C16—H160.9300
C4—C51.396 (4)C17—C181.385 (4)
C4—C131.503 (4)C17—C261.500 (4)
C5—C61.371 (4)C18—C191.379 (4)
C5—H50.9300C18—H180.9300
C6—H60.9300C19—H190.9300
C7—C121.392 (4)C20—C211.386 (4)
C7—C81.394 (4)C20—C251.392 (4)
C7—N11.413 (4)C20—N21.418 (3)
C8—C91.392 (4)C21—C221.396 (4)
C8—Cl11.716 (3)C21—Cl31.721 (3)
C9—C101.375 (5)C22—C231.378 (4)
C9—Cl21.719 (3)C22—Cl41.720 (3)
C10—C111.358 (6)C23—C241.361 (5)
C10—H100.9300C23—H230.9300
C11—C121.390 (5)C24—C251.397 (4)
C11—H110.9300C24—H240.9300
C12—H120.9300C25—H250.9300
C13—H13A0.9600C26—H26A0.9600
C13—H13B0.9600C26—H26B0.9600
C13—H13C0.9600C26—H26C0.9600
N1—S11.638 (2)N2—S21.645 (2)
N1—H1N0.837 (18)N2—H2N0.851 (18)
O1—S11.425 (2)O3—S21.430 (2)
O2—S11.436 (2)O4—S21.424 (2)
C6—C1—C2120.7 (2)C19—C14—C15121.2 (2)
C6—C1—S1119.5 (2)C19—C14—S2119.7 (2)
C2—C1—S1119.8 (2)C15—C14—S2119.1 (2)
C3—C2—C1118.9 (3)C16—C15—C14118.8 (2)
C3—C2—H2120.5C16—C15—H15120.6
C1—C2—H2120.5C14—C15—H15120.6
C2—C3—C4121.8 (3)C15—C16—C17121.5 (3)
C2—C3—H3119.1C15—C16—H16119.3
C4—C3—H3119.1C17—C16—H16119.3
C3—C4—C5118.1 (3)C18—C17—C16118.1 (3)
C3—C4—C13121.2 (3)C18—C17—C26121.5 (3)
C5—C4—C13120.6 (3)C16—C17—C26120.4 (3)
C6—C5—C4121.1 (3)C19—C18—C17121.5 (3)
C6—C5—H5119.5C19—C18—H18119.3
C4—C5—H5119.5C17—C18—H18119.3
C5—C6—C1119.4 (3)C18—C19—C14118.9 (3)
C5—C6—H6120.3C18—C19—H19120.6
C1—C6—H6120.3C14—C19—H19120.6
C12—C7—C8119.1 (3)C21—C20—C25118.5 (2)
C12—C7—N1120.8 (3)C21—C20—N2119.3 (2)
C8—C7—N1120.0 (3)C25—C20—N2122.1 (2)
C9—C8—C7120.0 (3)C20—C21—C22120.5 (2)
C9—C8—Cl1120.6 (2)C20—C21—Cl3119.61 (19)
C7—C8—Cl1119.4 (2)C22—C21—Cl3119.9 (2)
C10—C9—C8120.2 (3)C23—C22—C21120.6 (3)
C10—C9—Cl2119.5 (2)C23—C22—Cl4119.1 (2)
C8—C9—Cl2120.3 (2)C21—C22—Cl4120.2 (2)
C11—C10—C9119.8 (3)C24—C23—C22118.9 (3)
C11—C10—H10120.1C24—C23—H23120.5
C9—C10—H10120.1C22—C23—H23120.5
C10—C11—C12121.6 (3)C23—C24—C25121.7 (3)
C10—C11—H11119.2C23—C24—H24119.2
C12—C11—H11119.2C25—C24—H24119.2
C11—C12—C7119.2 (3)C20—C25—C24119.7 (3)
C11—C12—H12120.4C20—C25—H25120.1
C7—C12—H12120.4C24—C25—H25120.1
C4—C13—H13A109.5C17—C26—H26A109.5
C4—C13—H13B109.5C17—C26—H26B109.5
H13A—C13—H13B109.5H26A—C26—H26B109.5
C4—C13—H13C109.5C17—C26—H26C109.5
H13A—C13—H13C109.5H26A—C26—H26C109.5
H13B—C13—H13C109.5H26B—C26—H26C109.5
C7—N1—S1123.66 (19)C20—N2—S2124.27 (18)
C7—N1—H1N117 (2)C20—N2—H2N114 (2)
S1—N1—H1N107 (2)S2—N2—H2N113 (2)
O1—S1—O2119.51 (13)O4—S2—O3119.53 (12)
O1—S1—N1108.38 (13)O4—S2—N2108.34 (13)
O2—S1—N1104.38 (12)O3—S2—N2104.28 (12)
O1—S1—C1108.59 (13)O4—S2—C14108.40 (13)
O2—S1—C1108.57 (12)O3—S2—C14109.14 (13)
N1—S1—C1106.70 (12)N2—S2—C14106.39 (11)
C6—C1—C2—C30.7 (4)C19—C14—C15—C160.1 (4)
S1—C1—C2—C3−178.1 (2)S2—C14—C15—C16179.4 (2)
C1—C2—C3—C40.3 (4)C14—C15—C16—C17−0.5 (4)
C2—C3—C4—C5−1.3 (4)C15—C16—C17—C181.0 (4)
C2—C3—C4—C13178.9 (3)C15—C16—C17—C26−179.2 (3)
C3—C4—C5—C61.4 (4)C16—C17—C18—C19−1.1 (4)
C13—C4—C5—C6−178.8 (3)C26—C17—C18—C19179.1 (3)
C4—C5—C6—C1−0.5 (4)C17—C18—C19—C140.7 (4)
C2—C1—C6—C5−0.5 (4)C15—C14—C19—C18−0.2 (4)
S1—C1—C6—C5178.3 (2)S2—C14—C19—C18−179.5 (2)
C12—C7—C8—C90.8 (4)C25—C20—C21—C22−0.4 (4)
N1—C7—C8—C9−176.2 (2)N2—C20—C21—C22177.4 (2)
C12—C7—C8—Cl1−179.0 (2)C25—C20—C21—Cl3178.2 (2)
N1—C7—C8—Cl14.0 (3)N2—C20—C21—Cl3−4.0 (3)
C7—C8—C9—C10−1.9 (4)C20—C21—C22—C231.1 (4)
Cl1—C8—C9—C10177.9 (2)Cl3—C21—C22—C23−177.6 (2)
C7—C8—C9—Cl2178.22 (19)C20—C21—C22—Cl4179.30 (18)
Cl1—C8—C9—Cl2−2.0 (3)Cl3—C21—C22—Cl40.7 (3)
C8—C9—C10—C111.2 (5)C21—C22—C23—C24−0.3 (4)
Cl2—C9—C10—C11−178.9 (3)Cl4—C22—C23—C24−178.5 (2)
C9—C10—C11—C120.5 (6)C22—C23—C24—C25−1.2 (5)
C10—C11—C12—C7−1.7 (5)C21—C20—C25—C24−1.0 (4)
C8—C7—C12—C111.0 (4)N2—C20—C25—C24−178.8 (3)
N1—C7—C12—C11177.9 (3)C23—C24—C25—C201.9 (5)
C12—C7—N1—S147.9 (3)C21—C20—N2—S2150.1 (2)
C8—C7—N1—S1−135.2 (2)C25—C20—N2—S2−32.2 (3)
C7—N1—S1—O1−51.4 (2)C20—N2—S2—O454.7 (2)
C7—N1—S1—O2−179.8 (2)C20—N2—S2—O3−177.0 (2)
C7—N1—S1—C165.4 (2)C20—N2—S2—C14−61.7 (2)
C6—C1—S1—O1−169.9 (2)C19—C14—S2—O4−10.5 (2)
C2—C1—S1—O18.9 (3)C15—C14—S2—O4170.1 (2)
C6—C1—S1—O2−38.5 (3)C19—C14—S2—O3−142.2 (2)
C2—C1—S1—O2140.3 (2)C15—C14—S2—O338.4 (2)
C6—C1—S1—N173.5 (2)C19—C14—S2—N2105.8 (2)
C2—C1—S1—N1−107.8 (2)C15—C14—S2—N2−73.6 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O30.84 (2)2.29 (2)3.086 (3)160 (3)
N1—H1N···Cl10.84 (2)2.54 (3)2.957 (2)112 (3)
N2—H2N···O20.85 (2)2.32 (2)3.104 (3)154 (3)
N2—H2N···Cl30.85 (2)2.46 (3)2.944 (2)117 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2248).

References

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