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

In the title compound, C(12)H(9)ClN(2)O(4)S, the dihedral angle between the aromatic rings is 73.65 (7)°. The amide H atom shows bifurcated hydrogen bonding, generating an intra-molecular S(7) and an inter-molecular C(4) motif.

Related literature

For studies on 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-aryl­sulfonamides, see: Gowda et al. (2002 ▶) and of N-chloro­aryl­sulfonamides, see: Gowda & Shetty (2004 ▶); Shetty & Gowda (2004 ▶). For hydrogen-bonding patterns and motifs, see: Adsmond et al. (2001 ▶); Allen et al. (1998 ▶); Bernstein et al. (1995 ▶); Etter (1990 ▶).

Experimental

Crystal data

C12H9ClN2O4S

M = 312.72

Monoclinic,

a = 8.9856 (7) Å

b = 9.5794 (8) Å

c = 15.796 (1) Å

β = 103.120 (8)°

V = 1324.17 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.46 mm−1

T = 293 K

0.48 × 0.48 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.809, T max = 0.898

5230 measured reflections

2702 independent reflections

2201 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.100

S = 1.03

2702 reflections

184 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.51 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/S1600536812033272/bt5982sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033272/bt5982Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033272/bt5982Isup3.cml

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

C12H9ClN2O4S	F(000) = 640
Mr = 312.72	Dx = 1.569 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2323 reflections
a = 8.9856 (7) Å	θ = 2.6–27.8°
b = 9.5794 (8) Å	µ = 0.46 mm−1
c = 15.796 (1) Å	T = 293 K
β = 103.120 (8)°	Rod, colourless
V = 1324.17 (17) Å3	0.48 × 0.48 × 0.24 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2702 independent reflections
Radiation source: fine-focus sealed tube	2201 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 = −11→11
Tmin = 0.809, Tmax = 0.898	k = −11→10
5230 measured reflections	l = −19→15

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0414P)2 + 0.7223P] where P = (Fo2 + 2Fc2)/3
2702 reflections	(Δ/σ)max < 0.001
184 parameters	Δρmax = 0.39 e Å−3
1 restraint	Δρmin = −0.51 e Å−3

Experimental. Absorption correction: 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	0.1289 (2)	0.1345 (2)	0.41117 (13)	0.0364 (4)
C2	0.0829 (2)	0.1878 (2)	0.48339 (13)	0.0395 (5)
C3	0.1398 (3)	0.1350 (3)	0.56563 (14)	0.0523 (6)
H3	0.1062	0.1705	0.6128	0.063*
C4	0.2467 (3)	0.0298 (3)	0.57749 (17)	0.0606 (7)
H4	0.2859	−0.0054	0.6329	0.073*
C5	0.2954 (3)	−0.0235 (3)	0.50813 (18)	0.0578 (6)
H5	0.3687	−0.0938	0.5165	0.069*
C6	0.2350 (3)	0.0278 (2)	0.42487 (16)	0.0487 (5)
H6	0.2667	−0.0105	0.3778	0.058*
C7	0.2763 (2)	0.3656 (2)	0.30709 (12)	0.0350 (4)
C8	0.3206 (2)	0.4862 (2)	0.35429 (13)	0.0403 (5)
H8	0.2492	0.5418	0.3726	0.048*
C9	0.4733 (3)	0.5219 (3)	0.37354 (15)	0.0518 (6)
C10	0.5814 (3)	0.4401 (3)	0.34821 (19)	0.0673 (8)
H10	0.6839	0.4657	0.3619	0.081*
C11	0.5348 (3)	0.3200 (3)	0.3024 (2)	0.0681 (8)
H11	0.6072	0.2635	0.2855	0.082*
C12	0.3822 (3)	0.2810 (3)	0.28080 (16)	0.0518 (6)
H12	0.3518	0.1998	0.2493	0.062*
N1	0.11632 (18)	0.33458 (18)	0.28331 (11)	0.0370 (4)
H1N	0.064 (2)	0.398 (2)	0.2966 (14)	0.044*
N2	−0.0256 (2)	0.3049 (2)	0.47737 (12)	0.0466 (5)
O1	−0.11286 (16)	0.19931 (18)	0.28970 (10)	0.0530 (4)
O2	0.10397 (19)	0.08275 (17)	0.24876 (10)	0.0543 (4)
O3	−0.02102 (19)	0.39843 (19)	0.42550 (11)	0.0568 (4)
O4	−0.1124 (2)	0.3039 (2)	0.52670 (14)	0.0756 (6)
Cl1	0.52921 (10)	0.67414 (9)	0.43224 (5)	0.0871 (3)
S1	0.04801 (6)	0.18286 (6)	0.30104 (3)	0.03894 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0351 (10)	0.0342 (10)	0.0412 (10)	−0.0101 (8)	0.0112 (8)	−0.0039 (8)
C2	0.0373 (10)	0.0400 (12)	0.0428 (11)	−0.0128 (9)	0.0122 (8)	−0.0069 (9)
C3	0.0558 (14)	0.0600 (15)	0.0418 (12)	−0.0198 (12)	0.0128 (10)	−0.0053 (11)
C4	0.0624 (16)	0.0595 (16)	0.0550 (14)	−0.0185 (13)	0.0031 (12)	0.0140 (12)
C5	0.0468 (13)	0.0469 (14)	0.0770 (18)	−0.0033 (11)	0.0087 (12)	0.0124 (13)
C6	0.0481 (12)	0.0412 (12)	0.0606 (14)	−0.0033 (10)	0.0200 (10)	−0.0003 (11)
C7	0.0323 (10)	0.0396 (11)	0.0348 (10)	0.0003 (8)	0.0110 (8)	0.0069 (8)
C8	0.0388 (11)	0.0426 (12)	0.0409 (11)	−0.0022 (9)	0.0118 (8)	0.0069 (9)
C9	0.0441 (12)	0.0574 (15)	0.0518 (13)	−0.0154 (11)	0.0068 (10)	0.0139 (11)
C10	0.0340 (12)	0.080 (2)	0.0860 (19)	−0.0089 (13)	0.0097 (12)	0.0291 (16)
C11	0.0415 (13)	0.0696 (19)	0.100 (2)	0.0161 (13)	0.0311 (14)	0.0207 (16)
C12	0.0445 (12)	0.0476 (14)	0.0681 (15)	0.0053 (10)	0.0232 (11)	0.0053 (11)
N1	0.0313 (9)	0.0385 (10)	0.0425 (9)	0.0017 (7)	0.0111 (7)	−0.0010 (7)
N2	0.0455 (10)	0.0482 (11)	0.0501 (11)	−0.0116 (9)	0.0193 (8)	−0.0181 (9)
O1	0.0340 (8)	0.0703 (11)	0.0527 (9)	−0.0150 (7)	0.0058 (7)	−0.0102 (8)
O2	0.0677 (10)	0.0496 (10)	0.0501 (9)	−0.0113 (8)	0.0227 (8)	−0.0193 (7)
O3	0.0660 (11)	0.0543 (10)	0.0548 (10)	0.0076 (8)	0.0234 (8)	−0.0031 (8)
O4	0.0798 (13)	0.0675 (12)	0.1002 (15)	−0.0106 (10)	0.0640 (12)	−0.0179 (11)
Cl1	0.0842 (5)	0.0888 (6)	0.0840 (5)	−0.0501 (4)	0.0103 (4)	−0.0107 (4)
S1	0.0383 (3)	0.0421 (3)	0.0372 (3)	−0.0093 (2)	0.0102 (2)	−0.0102 (2)

C1—C6	1.381 (3)	C8—C9	1.379 (3)
C1—C2	1.395 (3)	C8—H8	0.9300
C1—S1	1.788 (2)	C9—C10	1.376 (4)
C2—C3	1.380 (3)	C9—Cl1	1.740 (3)
C2—N2	1.475 (3)	C10—C11	1.374 (4)
C3—C4	1.376 (4)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.387 (3)
C4—C5	1.368 (4)	C11—H11	0.9300
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.393 (3)	N1—S1	1.6265 (18)
C5—H5	0.9300	N1—H1N	0.823 (16)
C6—H6	0.9300	N2—O3	1.221 (2)
C7—C8	1.383 (3)	N2—O4	1.222 (2)
C7—C12	1.384 (3)	O1—S1	1.4243 (15)
C7—N1	1.432 (2)	O2—S1	1.4294 (16)
C6—C1—C2	117.7 (2)	C10—C9—C8	121.8 (2)
C6—C1—S1	117.27 (16)	C10—C9—Cl1	119.61 (19)
C2—C1—S1	124.76 (16)	C8—C9—Cl1	118.6 (2)
C3—C2—C1	121.3 (2)	C11—C10—C9	118.6 (2)
C3—C2—N2	116.0 (2)	C11—C10—H10	120.7
C1—C2—N2	122.67 (19)	C9—C10—H10	120.7
C4—C3—C2	119.7 (2)	C10—C11—C12	121.4 (2)
C4—C3—H3	120.2	C10—C11—H11	119.3
C2—C3—H3	120.2	C12—C11—H11	119.3
C5—C4—C3	120.3 (2)	C7—C12—C11	118.5 (2)
C5—C4—H4	119.8	C7—C12—H12	120.7
C3—C4—H4	119.8	C11—C12—H12	120.7
C4—C5—C6	119.8 (2)	C7—N1—S1	122.41 (14)
C4—C5—H5	120.1	C7—N1—H1N	112.1 (16)
C6—C5—H5	120.1	S1—N1—H1N	110.8 (16)
C1—C6—C5	121.1 (2)	O3—N2—O4	123.9 (2)
C1—C6—H6	119.5	O3—N2—C2	118.63 (17)
C5—C6—H6	119.5	O4—N2—C2	117.5 (2)
C8—C7—C12	121.12 (19)	O1—S1—O2	118.79 (10)
C8—C7—N1	117.65 (18)	O1—S1—N1	106.94 (10)
C12—C7—N1	121.2 (2)	O2—S1—N1	107.70 (9)
C9—C8—C7	118.5 (2)	O1—S1—C1	109.15 (9)
C9—C8—H8	120.8	O2—S1—C1	105.64 (10)
C7—C8—H8	120.8	N1—S1—C1	108.25 (9)
C6—C1—C2—C3	−0.7 (3)	C8—C7—C12—C11	−0.3 (3)
S1—C1—C2—C3	173.26 (16)	N1—C7—C12—C11	177.0 (2)
C6—C1—C2—N2	177.83 (18)	C10—C11—C12—C7	−0.5 (4)
S1—C1—C2—N2	−8.2 (3)	C8—C7—N1—S1	−129.76 (17)
C1—C2—C3—C4	1.4 (3)	C12—C7—N1—S1	52.8 (2)
N2—C2—C3—C4	−177.20 (19)	C3—C2—N2—O3	142.9 (2)
C2—C3—C4—C5	−0.6 (3)	C1—C2—N2—O3	−35.7 (3)
C3—C4—C5—C6	−0.9 (4)	C3—C2—N2—O4	−35.2 (3)
C2—C1—C6—C5	−0.8 (3)	C1—C2—N2—O4	146.2 (2)
S1—C1—C6—C5	−175.25 (17)	C7—N1—S1—O1	165.95 (15)
C4—C5—C6—C1	1.6 (3)	C7—N1—S1—O2	−65.32 (17)
C12—C7—C8—C9	1.1 (3)	C7—N1—S1—C1	48.46 (18)
N1—C7—C8—C9	−176.38 (18)	C6—C1—S1—O1	135.23 (16)
C7—C8—C9—C10	−1.0 (3)	C2—C1—S1—O1	−38.75 (19)
C7—C8—C9—Cl1	179.54 (15)	C6—C1—S1—O2	6.42 (18)
C8—C9—C10—C11	0.1 (4)	C2—C1—S1—O2	−167.56 (16)
Cl1—C9—C10—C11	179.6 (2)	C6—C1—S1—N1	−108.71 (17)
C9—C10—C11—C12	0.6 (4)	C2—C1—S1—N1	77.30 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.82 (2)	2.33 (2)	2.864 (2)	123 (2)
N1—H1N···O2i	0.82 (2)	2.33 (2)	3.061 (2)	148 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3	0.82 (2)	2.33 (2)	2.864 (2)	123 (2)
N1—H1N⋯O2i	0.82 (2)	2.33 (2)	3.061 (2)	148 (2)

Symmetry code: (i) .