N-(2-Chloro-phen-yl)-2-nitro-benzene-sulfonamide.

In the title compound, C(12)H(9)ClN(2)O(4)S, the N-H bond in the -SO(2)-NH- segment is syn to both the ortho-nitro group in the sulfonyl-benzene ring and the ortho-Cl atom in the aniline ring. The mol-ecule is twisted at the S-N bond with a torsion angle of 75.0 (2)°. The dihedral angle between the sulfonyl-benzene and aniline rings is 54.97 (11)°. The amide H atom shows bifurcated hydrogen bonding, generating S(7) and C(4) motifs. In the crystal, N-H⋯O(S) hydrogen bonds link the mol-ecules into chains.

Related literature

For studies of the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Alkan et al. (2011 ▶); Bowes et al. (2003 ▶); Gowda et al. (2000 ▶), Saeed et al. (2010 ▶); Shahwar et al. (2012 ▶), of N-aroylsulfonamides, see: Suchetan et al. (2012 ▶), of N-chloro­aryl­sulfonamides, see: Gowda et al. (2005 ▶); Shetty & Gowda (2004 ▶) and of N-bromo­aryl­sulfonamides, see: Gowda & Mahadevappa (1983 ▶); Usha & Gowda (2006 ▶). For hydrogen-bonding patterns and motifs, see: Adsmond & Grant (2001 ▶); Allen et al. (1998 ▶); Bernstein et al. (1995 ▶); Etter (1990 ▶).

Experimental

Crystal data

C12H9ClN2O4S

M = 312.72

Monoclinic,

a = 9.2477 (9) Å

b = 15.293 (1) Å

c = 10.4671 (9) Å

β = 108.66 (1)°

V = 1402.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.43 mm−1

T = 293 K

0.40 × 0.32 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.845, T max = 0.934

5456 measured reflections

2847 independent reflections

2331 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.098

S = 1.13

2847 reflections

184 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.37 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/S1600536812033107/sj5261sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033107/sj5261Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033107/sj5261Isup3.cml

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

C12H9ClN2O4S	F(000) = 640
Mr = 312.72	Dx = 1.481 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2659 reflections
a = 9.2477 (9) Å	θ = 2.6–27.9°
b = 15.293 (1) Å	µ = 0.43 mm−1
c = 10.4671 (9) Å	T = 293 K
β = 108.66 (1)°	Prism, colourless
V = 1402.5 (2) Å3	0.40 × 0.32 × 0.16 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2847 independent reflections
Radiation source: fine-focus sealed tube	2331 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −10→11
Tmin = 0.845, Tmax = 0.934	k = −10→19
5456 measured reflections	l = −13→8

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.0298P)2 + 1.0512P] where P = (Fo2 + 2Fc2)/3
2847 reflections	(Δ/σ)max = 0.001
184 parameters	Δρmax = 0.23 e Å−3
1 restraint	Δρmin = −0.37 e Å−3

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	0.3704 (3)	0.90407 (15)	0.1498 (2)	0.0399 (5)
C2	0.4480 (3)	0.97153 (16)	0.2333 (3)	0.0453 (6)
C3	0.4168 (4)	1.0576 (2)	0.1994 (4)	0.0742 (10)
H3	0.4712	1.1017	0.2556	0.089*
C4	0.3045 (5)	1.0777 (2)	0.0816 (4)	0.1019 (15)
H4	0.2812	1.1360	0.0583	0.122*
C5	0.2257 (5)	1.0125 (3)	−0.0026 (4)	0.0996 (14)
H5	0.1492	1.0269	−0.0821	0.120*
C6	0.2596 (4)	0.9256 (2)	0.0303 (3)	0.0654 (8)
H6	0.2078	0.8817	−0.0280	0.079*
C7	0.1554 (2)	0.74776 (15)	0.2396 (2)	0.0339 (5)
C8	0.0533 (3)	0.80681 (15)	0.2644 (2)	0.0393 (5)
C9	−0.1011 (3)	0.7882 (2)	0.2248 (3)	0.0555 (7)
H9	−0.1683	0.8267	0.2453	0.067*
C10	−0.1544 (3)	0.7124 (2)	0.1549 (3)	0.0667 (8)
H10	−0.2584	0.7002	0.1266	0.080*
C11	−0.0550 (3)	0.6547 (2)	0.1267 (3)	0.0621 (8)
H11	−0.0922	0.6042	0.0777	0.075*
C12	0.0997 (3)	0.67125 (17)	0.1705 (3)	0.0469 (6)
H12	0.1667	0.6310	0.1537	0.056*
N1	0.3166 (2)	0.76256 (13)	0.28819 (18)	0.0343 (4)
H1N	0.353 (3)	0.7839 (15)	0.3657 (18)	0.041*
N2	0.5643 (3)	0.95397 (14)	0.3642 (2)	0.0514 (6)
O1	0.3492 (2)	0.74417 (12)	0.06758 (17)	0.0559 (5)
O2	0.56839 (19)	0.78488 (12)	0.2647 (2)	0.0550 (5)
O3	0.5276 (2)	0.91073 (14)	0.44578 (19)	0.0627 (5)
O4	0.6898 (3)	0.98600 (16)	0.3829 (3)	0.0893 (8)
Cl1	0.11837 (8)	0.90467 (4)	0.34591 (7)	0.05248 (19)
S1	0.41059 (7)	0.79209 (4)	0.18966 (6)	0.03658 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0484 (13)	0.0379 (12)	0.0350 (12)	−0.0023 (11)	0.0155 (11)	0.0014 (10)
C2	0.0540 (15)	0.0361 (13)	0.0442 (14)	−0.0040 (11)	0.0134 (12)	0.0013 (11)
C3	0.100 (3)	0.0369 (15)	0.074 (2)	−0.0043 (16)	0.011 (2)	0.0045 (15)
C4	0.143 (4)	0.0470 (19)	0.089 (3)	0.012 (2)	0.000 (3)	0.0246 (19)
C5	0.127 (3)	0.076 (3)	0.063 (2)	0.014 (2)	−0.016 (2)	0.027 (2)
C6	0.082 (2)	0.0601 (18)	0.0405 (15)	−0.0023 (16)	0.0012 (15)	0.0051 (14)
C7	0.0377 (12)	0.0358 (12)	0.0304 (11)	−0.0014 (9)	0.0139 (10)	0.0016 (9)
C8	0.0421 (13)	0.0392 (13)	0.0388 (12)	0.0001 (10)	0.0159 (11)	0.0020 (10)
C9	0.0423 (14)	0.0621 (18)	0.0660 (18)	0.0035 (13)	0.0228 (13)	0.0020 (15)
C10	0.0417 (15)	0.077 (2)	0.081 (2)	−0.0157 (15)	0.0193 (15)	−0.0068 (18)
C11	0.0594 (17)	0.0566 (17)	0.070 (2)	−0.0251 (15)	0.0206 (16)	−0.0159 (15)
C12	0.0536 (15)	0.0398 (13)	0.0512 (15)	−0.0050 (11)	0.0221 (13)	−0.0055 (11)
N1	0.0365 (10)	0.0405 (11)	0.0274 (9)	−0.0006 (8)	0.0124 (8)	−0.0025 (8)
N2	0.0530 (13)	0.0391 (12)	0.0546 (14)	−0.0058 (10)	0.0065 (11)	−0.0084 (11)
O1	0.0866 (14)	0.0501 (10)	0.0439 (10)	−0.0153 (10)	0.0391 (10)	−0.0172 (8)
O2	0.0391 (9)	0.0486 (11)	0.0826 (13)	0.0060 (8)	0.0268 (9)	−0.0022 (10)
O3	0.0725 (13)	0.0634 (13)	0.0454 (11)	0.0022 (11)	0.0095 (10)	0.0042 (10)
O4	0.0606 (14)	0.0777 (16)	0.108 (2)	−0.0295 (12)	−0.0037 (13)	0.0032 (14)
Cl1	0.0585 (4)	0.0417 (3)	0.0616 (4)	0.0036 (3)	0.0253 (3)	−0.0108 (3)
S1	0.0433 (3)	0.0341 (3)	0.0387 (3)	−0.0010 (2)	0.0221 (3)	−0.0057 (2)

C1—C6	1.379 (4)	C8—C9	1.383 (3)
C1—C2	1.393 (3)	C8—Cl1	1.732 (2)
C1—S1	1.774 (2)	C9—C10	1.375 (4)
C2—C3	1.370 (4)	C9—H9	0.9300
C2—N2	1.471 (3)	C10—C11	1.373 (4)
C3—C4	1.370 (5)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.379 (4)
C4—C5	1.375 (5)	C11—H11	0.9300
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.384 (5)	N1—S1	1.6114 (18)
C5—H5	0.9300	N1—H1N	0.838 (16)
C6—H6	0.9300	N2—O3	1.211 (3)
C7—C12	1.385 (3)	N2—O4	1.216 (3)
C7—C8	1.390 (3)	O1—S1	1.4241 (17)
C7—N1	1.431 (3)	O2—S1	1.4230 (18)
C6—C1—C2	118.5 (2)	C10—C9—C8	119.5 (3)
C6—C1—S1	118.8 (2)	C10—C9—H9	120.2
C2—C1—S1	122.70 (19)	C8—C9—H9	120.2
C3—C2—C1	121.7 (3)	C11—C10—C9	120.3 (3)
C3—C2—N2	116.6 (2)	C11—C10—H10	119.8
C1—C2—N2	121.7 (2)	C9—C10—H10	119.8
C4—C3—C2	119.0 (3)	C10—C11—C12	120.4 (3)
C4—C3—H3	120.5	C10—C11—H11	119.8
C2—C3—H3	120.5	C12—C11—H11	119.8
C3—C4—C5	120.5 (3)	C11—C12—C7	120.1 (2)
C3—C4—H4	119.7	C11—C12—H12	119.9
C5—C4—H4	119.7	C7—C12—H12	119.9
C4—C5—C6	120.4 (3)	C7—N1—S1	122.05 (15)
C4—C5—H5	119.8	C7—N1—H1N	116.9 (17)
C6—C5—H5	119.8	S1—N1—H1N	112.4 (17)
C1—C6—C5	119.9 (3)	O3—N2—O4	125.1 (3)
C1—C6—H6	120.1	O3—N2—C2	118.0 (2)
C5—C6—H6	120.1	O4—N2—C2	116.9 (2)
C12—C7—C8	119.0 (2)	O2—S1—O1	119.96 (12)
C12—C7—N1	119.4 (2)	O2—S1—N1	107.04 (11)
C8—C7—N1	121.6 (2)	O1—S1—N1	106.75 (10)
C9—C8—C7	120.5 (2)	O2—S1—C1	107.77 (11)
C9—C8—Cl1	119.2 (2)	O1—S1—C1	107.01 (12)
C7—C8—Cl1	120.26 (18)	N1—S1—C1	107.80 (11)
C6—C1—C2—C3	0.0 (4)	C10—C11—C12—C7	−2.2 (4)
S1—C1—C2—C3	178.9 (2)	C8—C7—C12—C11	0.4 (4)
C6—C1—C2—N2	178.1 (3)	N1—C7—C12—C11	178.0 (2)
S1—C1—C2—N2	−3.0 (4)	C12—C7—N1—S1	76.6 (3)
C1—C2—C3—C4	1.2 (5)	C8—C7—N1—S1	−105.9 (2)
N2—C2—C3—C4	−177.0 (4)	C3—C2—N2—O3	121.6 (3)
C2—C3—C4—C5	−1.0 (7)	C1—C2—N2—O3	−56.6 (3)
C3—C4—C5—C6	−0.4 (8)	C3—C2—N2—O4	−56.8 (4)
C2—C1—C6—C5	−1.4 (5)	C1—C2—N2—O4	125.0 (3)
S1—C1—C6—C5	179.7 (3)	C7—N1—S1—O2	−169.32 (17)
C4—C5—C6—C1	1.6 (7)	C7—N1—S1—O1	−39.7 (2)
C12—C7—C8—C9	2.1 (4)	C7—N1—S1—C1	75.0 (2)
N1—C7—C8—C9	−175.4 (2)	C6—C1—S1—O2	147.7 (2)
C12—C7—C8—Cl1	−178.01 (18)	C2—C1—S1—O2	−31.2 (2)
N1—C7—C8—Cl1	4.5 (3)	C6—C1—S1—O1	17.4 (3)
C7—C8—C9—C10	−2.9 (4)	C2—C1—S1—O1	−161.5 (2)
Cl1—C8—C9—C10	177.2 (2)	C6—C1—S1—N1	−97.1 (2)
C8—C9—C10—C11	1.2 (5)	C2—C1—S1—N1	84.0 (2)
C9—C10—C11—C12	1.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.84 (2)	2.17 (2)	2.844 (2)	138 (2)
N1—H1N···O3	0.84 (2)	2.49 (2)	3.099 (3)	130 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.84 (2)	2.17 (2)	2.844 (2)	138 (2)
N1—H1N⋯O3	0.84 (2)	2.49 (2)	3.099 (3)	130 (2)

Symmetry code: (i) .