N-(3-Chloro-benzo-yl)-2-nitro-benzene-sulfonamide.

In the title compound, C(13)H(9)ClN(2)O(5)S, the N-C bond in the C-SO(2)-NH-C segment has a gauche torsion with respect to the S=O bonds. The conformation between the N-H bond and the ortho-nitro group in the sulfonyl benzene ring is syn, and that between the C=O and the meta-Cl atom in the benzoyl ring is anti. The mol-ecule is twisted at the S-N bond, with a torsion angle of 65.41 (38)°. The dihedral angle between the sulfonyl benzene ring and the -SO(2)-NH-C-O segment is 75.0 (1)°, and that between the sulfonyl and the benzoyl benzene ring is 89.1 (1)°. The crystal structure features inversion-related dimers linked by pairs of N-H⋯O(S) hydrogen bonds.

Related literature

For our studies of the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda et al. (1999 ▶, 2006 ▶); n class="Chemical">N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶); N-(substitutedbenzo­yl)-aryl­sulfonamides, see: Suchetan et al. (2012 ▶); N-chloro­aryl­amides, see: Jyothi & Gowda (2004 ▶) and N-bromo­aryl­sulfonamides, see: Usha & Gowda (2006 ▶)..

Experimental

Crystal data

C13H9ClN2O5S

M = 340.73

Orthorhombic,

a = 12.2046 (8) Å

b = 12.6121 (9) Å

c = 18.433 (1) Å

V = 2837.3 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.44 mm−1

T = 293 K

0.28 × 0.28 × 0.08 mm

Data collection

Oxford Xcalibur diffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.886, T max = 0.966

11298 measured reflections

2889 independent reflections

1911 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.147

S = 1.20

2889 reflections

202 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.29 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681200640X/nc2268sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200640X/nc2268Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681200640X/nc2268Isup3.cml

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

C13H9ClN2O5S	F(000) = 1392
Mr = 340.73	Dx = 1.595 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1818 reflections
a = 12.2046 (8) Å	θ = 2.6–27.9°
b = 12.6121 (9) Å	µ = 0.44 mm−1
c = 18.433 (1) Å	T = 293 K
V = 2837.3 (3) Å3	Rod, colourless
Z = 8	0.28 × 0.28 × 0.08 mm

Oxford Xcalibur diffractometer with Sapphire CCD detector	2889 independent reflections
Radiation source: fine-focus sealed tube	1911 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→15
Tmin = 0.886, Tmax = 0.966	k = −15→11
11298 measured reflections	l = −22→23

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.20	w = 1/[σ2(Fo2) + (0.0362P)2 + 4.7309P] where P = (Fo2 + 2Fc2)/3
2889 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.34 e Å−3
1 restraint	Δρmin = −0.29 e Å−3

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
C1	−0.0112 (3)	0.7252 (3)	0.0676 (2)	0.0347 (9)
C2	−0.0862 (3)	0.7030 (3)	0.0131 (2)	0.0402 (10)
C3	−0.1369 (4)	0.6063 (4)	0.0079 (3)	0.0503 (12)
H3	−0.1854	0.5924	−0.0298	0.060*
C4	−0.1152 (4)	0.5307 (4)	0.0590 (3)	0.0552 (13)
H4	−0.1498	0.4652	0.0563	0.066*
C5	−0.0427 (4)	0.5506 (4)	0.1143 (3)	0.0537 (13)
H5	−0.0286	0.4986	0.1488	0.064*
C6	0.0092 (4)	0.6469 (3)	0.1188 (2)	0.0450 (11)
H6	0.0582	0.6598	0.1564	0.054*
C7	−0.0490 (3)	0.9234 (3)	0.1845 (2)	0.0389 (10)
C8	−0.1239 (3)	1.0094 (3)	0.2089 (2)	0.0354 (9)
C9	−0.1284 (3)	1.1061 (3)	0.1738 (2)	0.0390 (10)
H9	−0.0812	1.1205	0.1354	0.047*
C10	−0.2036 (4)	1.1812 (3)	0.1960 (2)	0.0400 (10)
C11	−0.2730 (4)	1.1613 (4)	0.2528 (2)	0.0456 (11)
H11	−0.3240	1.2119	0.2672	0.055*
C12	−0.2663 (4)	1.0654 (4)	0.2884 (2)	0.0499 (12)
H12	−0.3127	1.0518	0.3273	0.060*
C13	−0.1921 (4)	0.9897 (3)	0.2670 (2)	0.0452 (11)
H13	−0.1879	0.9254	0.2915	0.054*
N1	−0.0153 (3)	0.9315 (3)	0.11212 (18)	0.0400 (9)
H1N	−0.050 (3)	0.966 (3)	0.0794 (18)	0.048*
N2	−0.1148 (3)	0.7825 (3)	−0.0428 (2)	0.0528 (10)
O1	0.0765 (2)	0.8844 (2)	−0.00038 (15)	0.0478 (8)
O2	0.1576 (2)	0.8265 (2)	0.11536 (16)	0.0514 (8)
O3	−0.0201 (3)	0.8509 (2)	0.22210 (16)	0.0538 (8)
O4	−0.1559 (3)	0.8640 (3)	−0.0218 (2)	0.0730 (11)
O5	−0.0955 (3)	0.7592 (3)	−0.10577 (18)	0.0747 (11)
Cl1	−0.20968 (12)	1.29932 (10)	0.14917 (7)	0.0697 (4)
S1	0.06425 (8)	0.84464 (8)	0.07160 (6)	0.0381 (3)

	U11	U22	U33	U12	U13	U23
C1	0.036 (2)	0.030 (2)	0.038 (2)	0.0025 (18)	0.0033 (19)	0.0001 (18)
C2	0.037 (2)	0.044 (3)	0.040 (2)	0.007 (2)	0.0002 (19)	0.011 (2)
C3	0.042 (3)	0.054 (3)	0.055 (3)	−0.004 (2)	−0.008 (2)	0.004 (2)
C4	0.063 (3)	0.037 (3)	0.066 (3)	−0.011 (2)	−0.001 (3)	0.007 (2)
C5	0.068 (3)	0.041 (3)	0.052 (3)	0.005 (2)	−0.005 (3)	0.013 (2)
C6	0.052 (3)	0.043 (3)	0.040 (2)	0.007 (2)	−0.010 (2)	0.003 (2)
C7	0.044 (3)	0.037 (2)	0.035 (2)	−0.004 (2)	0.0004 (19)	0.0011 (19)
C8	0.039 (2)	0.036 (2)	0.031 (2)	−0.003 (2)	0.0033 (18)	−0.0040 (17)
C9	0.043 (3)	0.041 (2)	0.033 (2)	−0.004 (2)	0.0097 (19)	−0.0018 (18)
C10	0.049 (3)	0.033 (2)	0.037 (2)	−0.004 (2)	0.001 (2)	−0.0022 (18)
C11	0.047 (3)	0.048 (3)	0.042 (2)	0.002 (2)	0.009 (2)	−0.013 (2)
C12	0.060 (3)	0.050 (3)	0.040 (2)	−0.008 (3)	0.018 (2)	−0.005 (2)
C13	0.061 (3)	0.037 (2)	0.037 (2)	−0.006 (2)	0.009 (2)	−0.0048 (19)
N1	0.048 (2)	0.040 (2)	0.0329 (19)	0.0065 (18)	0.0043 (16)	0.0036 (16)
N2	0.049 (2)	0.057 (3)	0.053 (3)	−0.004 (2)	−0.012 (2)	0.016 (2)
O1	0.0518 (19)	0.0507 (18)	0.0411 (16)	−0.0011 (15)	0.0137 (14)	0.0022 (14)
O2	0.0366 (17)	0.060 (2)	0.0577 (19)	0.0028 (16)	−0.0076 (15)	−0.0045 (16)
O3	0.068 (2)	0.0485 (19)	0.0450 (17)	0.0083 (18)	0.0041 (16)	0.0094 (16)
O4	0.090 (3)	0.052 (2)	0.077 (3)	0.018 (2)	−0.007 (2)	0.0162 (19)
O5	0.087 (3)	0.098 (3)	0.0394 (19)	−0.011 (2)	−0.0108 (19)	0.0131 (19)
Cl1	0.0894 (11)	0.0479 (7)	0.0718 (9)	0.0188 (7)	0.0221 (7)	0.0146 (6)
S1	0.0379 (6)	0.0399 (6)	0.0365 (5)	0.0018 (5)	0.0035 (5)	−0.0007 (5)

C1—C6	1.388 (5)	C8—C9	1.382 (5)
C1—C2	1.389 (6)	C9—C10	1.381 (6)
C1—S1	1.767 (4)	C9—H9	0.9300
C2—C3	1.371 (6)	C10—C11	1.369 (6)
C2—N2	1.479 (5)	C10—Cl1	1.723 (4)
C3—C4	1.366 (6)	C11—C12	1.378 (6)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.373 (6)	C12—C13	1.374 (6)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.372 (6)	C13—H13	0.9300
C5—H5	0.9300	N1—S1	1.643 (4)
C6—H6	0.9300	N1—H1N	0.857 (19)
C7—O3	1.201 (5)	N2—O4	1.207 (5)
C7—N1	1.399 (5)	N2—O5	1.221 (5)
C7—C8	1.489 (6)	O1—S1	1.426 (3)
C8—C13	1.379 (5)	O2—S1	1.414 (3)
C6—C1—C2	117.8 (4)	C8—C9—H9	120.2
C6—C1—S1	119.0 (3)	C11—C10—C9	120.8 (4)
C2—C1—S1	123.1 (3)	C11—C10—Cl1	121.0 (3)
C3—C2—C1	121.9 (4)	C9—C10—Cl1	118.2 (3)
C3—C2—N2	116.7 (4)	C10—C11—C12	119.2 (4)
C1—C2—N2	121.5 (4)	C10—C11—H11	120.4
C4—C3—C2	119.0 (4)	C12—C11—H11	120.4
C4—C3—H3	120.5	C13—C12—C11	120.8 (4)
C2—C3—H3	120.5	C13—C12—H12	119.6
C3—C4—C5	120.7 (4)	C11—C12—H12	119.6
C3—C4—H4	119.7	C12—C13—C8	119.7 (4)
C5—C4—H4	119.7	C12—C13—H13	120.2
C6—C5—C4	120.2 (4)	C8—C13—H13	120.2
C6—C5—H5	119.9	C7—N1—S1	123.9 (3)
C4—C5—H5	119.9	C7—N1—H1N	124 (3)
C5—C6—C1	120.4 (4)	S1—N1—H1N	108 (3)
C5—C6—H6	119.8	O4—N2—O5	126.1 (4)
C1—C6—H6	119.8	O4—N2—C2	116.9 (4)
O3—C7—N1	121.3 (4)	O5—N2—C2	117.0 (4)
O3—C7—C8	124.1 (4)	O2—S1—O1	120.19 (19)
N1—C7—C8	114.5 (4)	O2—S1—N1	108.94 (18)
C13—C8—C9	119.9 (4)	O1—S1—N1	104.51 (18)
C13—C8—C7	118.3 (4)	O2—S1—C1	107.76 (19)
C9—C8—C7	121.7 (4)	O1—S1—C1	108.41 (19)
C10—C9—C8	119.5 (4)	N1—S1—C1	106.23 (18)
C10—C9—H9	120.2
C6—C1—C2—C3	−1.8 (6)	Cl1—C10—C11—C12	179.3 (3)
S1—C1—C2—C3	174.5 (3)	C10—C11—C12—C13	−0.7 (7)
C6—C1—C2—N2	178.6 (4)	C11—C12—C13—C8	−0.4 (7)
S1—C1—C2—N2	−5.0 (6)	C9—C8—C13—C12	1.7 (6)
C1—C2—C3—C4	1.8 (7)	C7—C8—C13—C12	−176.5 (4)
N2—C2—C3—C4	−178.7 (4)	O3—C7—N1—S1	0.6 (6)
C2—C3—C4—C5	−0.7 (7)	C8—C7—N1—S1	−178.1 (3)
C3—C4—C5—C6	−0.2 (7)	C3—C2—N2—O4	119.2 (5)
C4—C5—C6—C1	0.1 (7)	C1—C2—N2—O4	−61.2 (6)
C2—C1—C6—C5	0.9 (6)	C3—C2—N2—O5	−60.2 (6)
S1—C1—C6—C5	−175.6 (3)	C1—C2—N2—O5	119.4 (5)
O3—C7—C8—C13	−22.3 (6)	C7—N1—S1—O2	−50.4 (4)
N1—C7—C8—C13	156.3 (4)	C7—N1—S1—O1	179.9 (3)
O3—C7—C8—C9	159.5 (4)	C7—N1—S1—C1	65.4 (4)
N1—C7—C8—C9	−21.9 (6)	C6—C1—S1—O2	17.3 (4)
C13—C8—C9—C10	−1.7 (6)	C2—C1—S1—O2	−159.0 (3)
C7—C8—C9—C10	176.4 (4)	C6—C1—S1—O1	148.9 (3)
C8—C9—C10—C11	0.5 (6)	C2—C1—S1—O1	−27.4 (4)
C8—C9—C10—Cl1	−178.1 (3)	C6—C1—S1—N1	−99.3 (3)
C9—C10—C11—C12	0.7 (7)	C2—C1—S1—N1	84.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86 (2)	2.41 (3)	3.193 (4)	153 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86 (2)	2.41 (3)	3.193 (4)	153 (4)

Symmetry code: (i) .