N-(2-Chloro-phen-yl)-4-nitro-benzene-sulfonamide.

In the title compound, C12H9ClN2O4S, the dihedral angle between the benzene rings is 70.60 (11)°. An intra-molecular N-H⋯Cl contact occurs. In the crystal, mol-ecules form inversion dimers via pairs of N-H⋯O hydrogen bonds.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-aryl­sulfonamides, see: Chaithanya et al. (2012 ▶); Gowda et al. (2005 ▶) and of N-chloro­aryl­amides, see: Gowda & Shetty (2004 ▶); Gowda & Weiss (1994 ▶); 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 = 9.2762 (9) Å

b = 12.981 (1) Å

c = 11.970 (1) Å

β = 110.97 (1)°

V = 1345.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.45 mm−1

T = 293 K

0.42 × 0.20 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.833, T max = 0.956

5256 measured reflections

2748 independent reflections

2019 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.110

S = 1.16

2748 reflections

185 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.30 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812048684/bt6858sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048684/bt6858Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812048684/bt6858Isup3.cml

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

C12H9ClN2O4S	F(000) = 640
Mr = 312.72	Dx = 1.543 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1413 reflections
a = 9.2762 (9) Å	θ = 2.9–27.9°
b = 12.981 (1) Å	µ = 0.45 mm−1
c = 11.970 (1) Å	T = 293 K
β = 110.97 (1)°	Prism, light pink
V = 1345.9 (2) Å3	0.42 × 0.20 × 0.10 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2748 independent reflections
Radiation source: fine-focus sealed tube	2019 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −11→10
Tmin = 0.833, Tmax = 0.956	k = −11→16
5256 measured reflections	l = −11→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0185P)2 + 1.7246P] where P = (Fo2 + 2Fc2)/3
S = 1.16	(Δ/σ)max = 0.001
2748 reflections	Δρmax = 0.29 e Å−3
185 parameters	Δρmin = −0.30 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0098 (7)

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	0.1263 (3)	0.5209 (2)	0.4016 (3)	0.0343 (7)
C2	0.1763 (4)	0.6204 (3)	0.4357 (3)	0.0507 (9)
H2	0.2802	0.6331	0.4784	0.061*
C3	0.0722 (4)	0.7003 (3)	0.4066 (3)	0.0539 (9)
H3	0.1040	0.7676	0.4289	0.065*
C4	−0.0808 (4)	0.6778 (3)	0.3434 (3)	0.0444 (8)
C5	−0.1329 (4)	0.5798 (3)	0.3102 (3)	0.0430 (8)
H5	−0.2372	0.5673	0.2688	0.052*
C6	−0.0280 (3)	0.4996 (3)	0.3394 (3)	0.0375 (7)
H6	−0.0606	0.4324	0.3175	0.045*
C7	0.2457 (3)	0.4074 (2)	0.2074 (3)	0.0366 (7)
C8	0.2726 (3)	0.4687 (2)	0.1220 (3)	0.0401 (7)
C9	0.1904 (4)	0.4540 (3)	0.0011 (3)	0.0520 (9)
H9	0.2115	0.4943	−0.0554	0.062*
C10	0.0775 (4)	0.3798 (3)	−0.0351 (3)	0.0573 (10)
H10	0.0215	0.3701	−0.1161	0.069*
C11	0.0477 (4)	0.3202 (3)	0.0484 (3)	0.0550 (10)
H11	−0.0307	0.2713	0.0237	0.066*
C12	0.1327 (4)	0.3317 (3)	0.1695 (3)	0.0486 (9)
H12	0.1141	0.2889	0.2251	0.058*
N1	0.3366 (3)	0.4207 (2)	0.3307 (2)	0.0399 (6)
H1N	0.407 (3)	0.465 (2)	0.348 (3)	0.048*
N2	−0.1922 (4)	0.7636 (3)	0.3102 (3)	0.0653 (9)
O1	0.3880 (2)	0.44640 (19)	0.54360 (19)	0.0490 (6)
O2	0.1828 (2)	0.32555 (17)	0.4305 (2)	0.0460 (6)
O3	−0.3263 (3)	0.7440 (3)	0.2546 (3)	0.0967 (11)
O4	−0.1448 (4)	0.8497 (3)	0.3400 (4)	0.1119 (14)
Cl1	0.40864 (11)	0.56660 (7)	0.16532 (8)	0.0596 (3)
S1	0.26320 (9)	0.41991 (6)	0.43645 (7)	0.0372 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0355 (16)	0.0356 (17)	0.0334 (16)	−0.0036 (14)	0.0144 (13)	0.0015 (13)
C2	0.0380 (18)	0.045 (2)	0.063 (2)	−0.0078 (16)	0.0104 (17)	0.0001 (18)
C3	0.053 (2)	0.0350 (19)	0.072 (2)	−0.0039 (17)	0.0198 (19)	−0.0011 (18)
C4	0.0448 (18)	0.043 (2)	0.050 (2)	0.0092 (16)	0.0232 (16)	0.0072 (16)
C5	0.0344 (16)	0.051 (2)	0.0433 (18)	−0.0011 (16)	0.0141 (14)	0.0003 (17)
C6	0.0348 (16)	0.0393 (18)	0.0392 (17)	−0.0051 (14)	0.0144 (14)	−0.0047 (14)
C7	0.0358 (15)	0.0373 (17)	0.0371 (16)	0.0028 (14)	0.0136 (13)	−0.0044 (14)
C8	0.0391 (17)	0.0385 (18)	0.0419 (18)	0.0003 (15)	0.0135 (14)	−0.0026 (15)
C9	0.058 (2)	0.056 (2)	0.042 (2)	−0.0009 (19)	0.0178 (17)	−0.0003 (17)
C10	0.056 (2)	0.069 (3)	0.042 (2)	−0.004 (2)	0.0126 (18)	−0.0138 (19)
C11	0.047 (2)	0.058 (2)	0.060 (2)	−0.0154 (18)	0.0185 (18)	−0.023 (2)
C12	0.0500 (19)	0.048 (2)	0.051 (2)	−0.0104 (17)	0.0220 (17)	−0.0074 (17)
N1	0.0346 (14)	0.0450 (16)	0.0398 (14)	−0.0029 (13)	0.0131 (12)	−0.0010 (13)
N2	0.061 (2)	0.053 (2)	0.086 (3)	0.0140 (18)	0.033 (2)	0.0111 (19)
O1	0.0384 (12)	0.0669 (17)	0.0355 (12)	−0.0016 (11)	0.0056 (10)	0.0057 (11)
O2	0.0487 (13)	0.0389 (13)	0.0511 (14)	−0.0024 (11)	0.0188 (11)	0.0085 (11)
O3	0.0542 (18)	0.076 (2)	0.145 (3)	0.0226 (17)	0.018 (2)	0.014 (2)
O4	0.090 (2)	0.0459 (19)	0.187 (4)	0.0172 (18)	0.034 (3)	0.002 (2)
Cl1	0.0682 (6)	0.0530 (6)	0.0543 (6)	−0.0196 (5)	0.0179 (5)	0.0023 (4)
S1	0.0343 (4)	0.0411 (5)	0.0348 (4)	0.0007 (4)	0.0106 (3)	0.0052 (4)

C1—C2	1.383 (4)	C8—C9	1.386 (4)
C1—C6	1.385 (4)	C8—Cl1	1.735 (3)
C1—S1	1.768 (3)	C9—C10	1.374 (5)
C2—C3	1.375 (5)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.367 (5)
C3—C4	1.380 (5)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.388 (5)
C4—C5	1.369 (5)	C11—H11	0.9300
C4—N2	1.474 (4)	C12—H12	0.9300
C5—C6	1.381 (4)	N1—S1	1.637 (3)
C5—H5	0.9300	N1—H1N	0.837 (18)
C6—H6	0.9300	N2—O4	1.207 (4)
C7—C8	1.386 (4)	N2—O3	1.210 (4)
C7—C12	1.390 (4)	O1—S1	1.429 (2)
C7—N1	1.425 (4)	O2—S1	1.423 (2)
C2—C1—C6	121.2 (3)	C10—C9—C8	119.9 (3)
C2—C1—S1	119.1 (2)	C10—C9—H9	120.1
C6—C1—S1	119.7 (2)	C8—C9—H9	120.1
C3—C2—C1	119.9 (3)	C11—C10—C9	119.8 (3)
C3—C2—H2	120.0	C11—C10—H10	120.1
C1—C2—H2	120.0	C9—C10—H10	120.1
C2—C3—C4	118.0 (3)	C10—C11—C12	120.9 (3)
C2—C3—H3	121.0	C10—C11—H11	119.5
C4—C3—H3	121.0	C12—C11—H11	119.5
C5—C4—C3	122.9 (3)	C11—C12—C7	119.8 (3)
C5—C4—N2	119.0 (3)	C11—C12—H12	120.1
C3—C4—N2	118.1 (3)	C7—C12—H12	120.1
C4—C5—C6	118.9 (3)	C7—N1—S1	123.0 (2)
C4—C5—H5	120.5	C7—N1—H1N	117 (2)
C6—C5—H5	120.5	S1—N1—H1N	108 (2)
C5—C6—C1	119.0 (3)	O4—N2—O3	123.4 (4)
C5—C6—H6	120.5	O4—N2—C4	118.4 (4)
C1—C6—H6	120.5	O3—N2—C4	118.2 (4)
C8—C7—C12	118.6 (3)	O2—S1—O1	119.60 (14)
C8—C7—N1	120.0 (3)	O2—S1—N1	108.81 (14)
C12—C7—N1	121.4 (3)	O1—S1—N1	105.37 (13)
C9—C8—C7	120.9 (3)	O2—S1—C1	107.88 (14)
C9—C8—Cl1	118.9 (3)	O1—S1—C1	108.43 (15)
C7—C8—Cl1	120.2 (2)	N1—S1—C1	105.99 (14)
C6—C1—C2—C3	−0.8 (5)	C10—C11—C12—C7	2.6 (5)
S1—C1—C2—C3	178.2 (3)	C8—C7—C12—C11	−1.2 (5)
C1—C2—C3—C4	0.0 (5)	N1—C7—C12—C11	−179.2 (3)
C2—C3—C4—C5	0.9 (5)	C8—C7—N1—S1	137.5 (3)
C2—C3—C4—N2	−179.0 (3)	C12—C7—N1—S1	−44.6 (4)
C3—C4—C5—C6	−1.1 (5)	C5—C4—N2—O4	180.0 (4)
N2—C4—C5—C6	178.8 (3)	C3—C4—N2—O4	−0.1 (6)
C4—C5—C6—C1	0.3 (5)	C5—C4—N2—O3	0.0 (5)
C2—C1—C6—C5	0.6 (5)	C3—C4—N2—O3	179.9 (4)
S1—C1—C6—C5	−178.4 (2)	C7—N1—S1—O2	56.7 (3)
C12—C7—C8—C9	−0.9 (5)	C7—N1—S1—O1	−173.9 (3)
N1—C7—C8—C9	177.1 (3)	C7—N1—S1—C1	−59.1 (3)
C12—C7—C8—Cl1	178.1 (2)	C2—C1—S1—O2	160.4 (3)
N1—C7—C8—Cl1	−3.9 (4)	C6—C1—S1—O2	−20.6 (3)
C7—C8—C9—C10	1.8 (5)	C2—C1—S1—O1	29.5 (3)
Cl1—C8—C9—C10	−177.3 (3)	C6—C1—S1—O1	−151.5 (2)
C8—C9—C10—C11	−0.5 (6)	C2—C1—S1—N1	−83.2 (3)
C9—C10—C11—C12	−1.7 (6)	C6—C1—S1—N1	95.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.84 (2)	2.20 (2)	3.003 (3)	159 (3)
N1—H1N···Cl1	0.84 (2)	2.56 (3)	2.984 (3)	112 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.84 (2)	2.20 (2)	3.003 (3)	159 (3)
N1—H1N⋯Cl1	0.84 (2)	2.56 (3)	2.984 (3)	112 (3)

Symmetry code: (i) .