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

In the title compound, C(13)H(9)ClN(2)O(5)S, the dihedral angle between the two rings is 71.2 (1)°. The crystal structure features inversion dimers linked by pairs of N-H⋯O(S) hydrogen bonds.

Related literature

For studies, including our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Bowes et al. (2003 ▶); Gowda et al. (2006 ▶), on N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶), on N-(ar­yl)-aryl­sulfonamides, see: Shetty & Gowda (2005 ▶), on N-(substitutedbenzo­yl)-aryl­sulfon­amides, see: Suchetan et al. (2012 ▶) and on N-chloro­aryl­amides, see: Gowda & Mahadevappa (1983 ▶).

Experimental

Crystal data

C13H9ClN2O5S

M = 340.73

Orthorhombic,

a = 12.266 (1) Å

b = 12.643 (1) Å

c = 18.738 (2) Å

V = 2905.9 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.43 mm−1

T = 293 K

0.48 × 0.40 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.820, T max = 0.919

7231 measured reflections

2958 independent reflections

2105 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.096

S = 1.04

2958 reflections

202 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 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/S1600536811054882/bt5759sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054882/bt5759Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811054882/bt5759Isup3.cml

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

C13H9ClN2O5S	F(000) = 1392
Mr = 340.73	Dx = 1.558 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2278 reflections
a = 12.266 (1) Å	θ = 2.5–27.7°
b = 12.643 (1) Å	µ = 0.43 mm−1
c = 18.738 (2) Å	T = 293 K
V = 2905.9 (5) Å3	Prism, colourless
Z = 8	0.48 × 0.40 × 0.20 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2958 independent reflections
Radiation source: fine-focus sealed tube	2105 reflections with I > 2σ(I)
graphite	Rint = 0.015
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→15
Tmin = 0.820, Tmax = 0.919	k = −12→15
7231 measured reflections	l = −23→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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.052P)2 + 0.3259P] where P = (Fo2 + 2Fc2)/3
2958 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.23 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	0.08013 (14)	0.23007 (14)	0.52361 (9)	0.0378 (4)
C2	0.00268 (15)	0.21928 (14)	0.57758 (10)	0.0414 (4)
C3	−0.01230 (19)	0.12473 (16)	0.61266 (12)	0.0579 (6)
H3	−0.0641	0.1194	0.6487	0.069*
C4	0.0493 (2)	0.03845 (17)	0.59424 (14)	0.0698 (7)
H4	0.0393	−0.0256	0.6178	0.084*
C5	0.12540 (19)	0.04664 (18)	0.54136 (14)	0.0679 (7)
H5	0.1667	−0.0122	0.5288	0.081*
C6	0.14160 (17)	0.14199 (16)	0.50620 (12)	0.0523 (5)
H6	0.1942	0.1467	0.4706	0.063*
C7	−0.00470 (16)	0.32241 (14)	0.36776 (9)	0.0409 (4)
C8	−0.08836 (15)	0.37301 (15)	0.32102 (9)	0.0396 (4)
C9	−0.18466 (17)	0.32223 (16)	0.30359 (11)	0.0504 (5)
C10	−0.2584 (2)	0.3683 (2)	0.25752 (13)	0.0705 (7)
H10	−0.3228	0.3334	0.2459	0.085*
C11	−0.2364 (2)	0.4656 (2)	0.22895 (13)	0.0741 (7)
H11	−0.2859	0.4962	0.1976	0.089*
C12	−0.1425 (2)	0.51844 (19)	0.24594 (11)	0.0638 (7)
H12	−0.1283	0.5846	0.2263	0.077*
C13	−0.06890 (18)	0.47285 (16)	0.29256 (10)	0.0496 (5)
H13	−0.0058	0.5092	0.3050	0.060*
N1	0.02375 (13)	0.38393 (11)	0.42595 (8)	0.0391 (4)
H1N	−0.0179 (15)	0.4312 (12)	0.4385 (10)	0.047*
N2	−0.06860 (14)	0.30632 (13)	0.60028 (10)	0.0515 (4)
O1	0.21732 (10)	0.33502 (11)	0.44685 (8)	0.0546 (4)
O2	0.11350 (10)	0.43253 (10)	0.53775 (7)	0.0425 (3)
O3	0.03763 (13)	0.23796 (11)	0.35641 (8)	0.0616 (4)
O4	−0.10433 (11)	0.36567 (12)	0.55488 (9)	0.0617 (4)
O5	−0.08870 (17)	0.31359 (14)	0.66363 (9)	0.0915 (6)
Cl1	−0.21604 (5)	0.20111 (5)	0.34182 (4)	0.0802 (2)
S1	0.11830 (4)	0.35192 (4)	0.48410 (2)	0.03738 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0299 (9)	0.0363 (9)	0.0473 (11)	0.0011 (8)	−0.0029 (8)	0.0011 (8)
C2	0.0403 (10)	0.0352 (9)	0.0487 (11)	0.0010 (8)	0.0007 (9)	0.0025 (8)
C3	0.0635 (14)	0.0468 (12)	0.0634 (13)	−0.0006 (11)	0.0106 (11)	0.0138 (10)
C4	0.0751 (17)	0.0445 (12)	0.0897 (19)	0.0078 (12)	0.0053 (15)	0.0198 (12)
C5	0.0591 (14)	0.0412 (12)	0.103 (2)	0.0199 (11)	0.0002 (14)	0.0047 (12)
C6	0.0400 (11)	0.0453 (11)	0.0716 (14)	0.0073 (9)	0.0082 (10)	−0.0014 (10)
C7	0.0458 (11)	0.0393 (10)	0.0377 (10)	−0.0012 (9)	0.0036 (9)	−0.0050 (8)
C8	0.0442 (10)	0.0427 (10)	0.0319 (9)	0.0040 (9)	0.0023 (8)	−0.0100 (8)
C9	0.0492 (12)	0.0554 (12)	0.0467 (11)	−0.0016 (10)	0.0015 (10)	−0.0117 (10)
C10	0.0534 (14)	0.0891 (18)	0.0689 (14)	0.0072 (14)	−0.0158 (12)	−0.0157 (15)
C11	0.0748 (18)	0.0890 (19)	0.0585 (14)	0.0365 (16)	−0.0122 (14)	−0.0051 (13)
C12	0.0891 (19)	0.0533 (13)	0.0490 (12)	0.0234 (13)	0.0107 (13)	0.0015 (11)
C13	0.0622 (13)	0.0445 (11)	0.0420 (10)	0.0046 (10)	0.0013 (10)	−0.0058 (9)
N1	0.0427 (9)	0.0377 (8)	0.0369 (8)	0.0057 (7)	−0.0033 (7)	−0.0040 (7)
N2	0.0510 (10)	0.0386 (9)	0.0648 (12)	−0.0051 (9)	0.0179 (9)	−0.0005 (8)
O1	0.0371 (8)	0.0643 (9)	0.0626 (9)	−0.0019 (7)	0.0130 (7)	0.0056 (7)
O2	0.0455 (7)	0.0375 (7)	0.0444 (7)	−0.0043 (6)	−0.0091 (6)	−0.0018 (5)
O3	0.0694 (10)	0.0515 (9)	0.0638 (10)	0.0196 (8)	−0.0084 (8)	−0.0189 (7)
O4	0.0478 (9)	0.0516 (9)	0.0857 (11)	0.0121 (7)	0.0126 (8)	0.0112 (9)
O5	0.1402 (18)	0.0662 (11)	0.0681 (12)	0.0066 (11)	0.0497 (12)	−0.0041 (9)
Cl1	0.0745 (5)	0.0688 (4)	0.0972 (5)	−0.0255 (3)	0.0024 (4)	−0.0002 (3)
S1	0.0315 (2)	0.0384 (3)	0.0423 (3)	−0.0029 (2)	0.0002 (2)	0.0017 (2)

C1—C6	1.384 (3)	C8—C13	1.391 (3)
C1—C2	1.394 (2)	C9—C10	1.379 (3)
C1—S1	1.7721 (18)	C9—Cl1	1.734 (2)
C2—C3	1.376 (3)	C10—C11	1.369 (3)
C2—N2	1.468 (2)	C10—H10	0.9300
C3—C4	1.371 (3)	C11—C12	1.369 (3)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.365 (3)	C12—C13	1.382 (3)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.388 (3)	C13—H13	0.9300
C5—H5	0.9300	N1—S1	1.6420 (16)
C6—H6	0.9300	N1—H1N	0.820 (14)
C7—O3	1.206 (2)	N2—O5	1.216 (2)
C7—N1	1.384 (2)	N2—O4	1.216 (2)
C7—C8	1.493 (3)	O1—S1	1.4171 (13)
C8—C9	1.384 (3)	O2—S1	1.4327 (13)
C6—C1—C2	117.61 (17)	C8—C9—Cl1	120.13 (16)
C6—C1—S1	117.21 (15)	C11—C10—C9	119.6 (2)
C2—C1—S1	124.62 (14)	C11—C10—H10	120.2
C3—C2—C1	121.49 (18)	C9—C10—H10	120.2
C3—C2—N2	115.66 (17)	C10—C11—C12	120.9 (2)
C1—C2—N2	122.85 (16)	C10—C11—H11	119.5
C4—C3—C2	119.8 (2)	C12—C11—H11	119.5
C4—C3—H3	120.1	C11—C12—C13	119.5 (2)
C2—C3—H3	120.1	C11—C12—H12	120.2
C5—C4—C3	120.0 (2)	C13—C12—H12	120.2
C5—C4—H4	120.0	C12—C13—C8	120.6 (2)
C3—C4—H4	120.0	C12—C13—H13	119.7
C4—C5—C6	120.5 (2)	C8—C13—H13	119.7
C4—C5—H5	119.7	C7—N1—S1	124.22 (13)
C6—C5—H5	119.7	C7—N1—H1N	118.5 (14)
C1—C6—C5	120.6 (2)	S1—N1—H1N	115.4 (14)
C1—C6—H6	119.7	O5—N2—O4	124.28 (19)
C5—C6—H6	119.7	O5—N2—C2	117.40 (18)
O3—C7—N1	121.86 (18)	O4—N2—C2	118.31 (17)
O3—C7—C8	124.88 (17)	O1—S1—O2	119.21 (8)
N1—C7—C8	113.24 (15)	O1—S1—N1	108.40 (8)
C9—C8—C13	118.50 (19)	O2—S1—N1	105.14 (7)
C9—C8—C7	121.76 (18)	O1—S1—C1	107.53 (8)
C13—C8—C7	119.73 (17)	O2—S1—C1	108.33 (8)
C10—C9—C8	120.8 (2)	N1—S1—C1	107.76 (8)
C10—C9—Cl1	119.05 (18)
C6—C1—C2—C3	0.2 (3)	C9—C10—C11—C12	−0.6 (4)
S1—C1—C2—C3	−170.90 (16)	C10—C11—C12—C13	0.1 (3)
C6—C1—C2—N2	−179.14 (18)	C11—C12—C13—C8	1.4 (3)
S1—C1—C2—N2	9.8 (3)	C9—C8—C13—C12	−2.3 (3)
C1—C2—C3—C4	−0.5 (3)	C7—C8—C13—C12	176.28 (17)
N2—C2—C3—C4	178.9 (2)	O3—C7—N1—S1	1.6 (3)
C2—C3—C4—C5	0.1 (4)	C8—C7—N1—S1	−176.52 (12)
C3—C4—C5—C6	0.4 (4)	C3—C2—N2—O5	38.4 (3)
C2—C1—C6—C5	0.4 (3)	C1—C2—N2—O5	−142.2 (2)
S1—C1—C6—C5	172.14 (18)	C3—C2—N2—O4	−141.0 (2)
C4—C5—C6—C1	−0.7 (4)	C1—C2—N2—O4	38.4 (3)
O3—C7—C8—C9	56.4 (3)	C7—N1—S1—O1	56.41 (17)
N1—C7—C8—C9	−125.56 (19)	C7—N1—S1—O2	−175.07 (15)
O3—C7—C8—C13	−122.1 (2)	C7—N1—S1—C1	−59.68 (17)
N1—C7—C8—C13	56.0 (2)	C6—C1—S1—O1	−6.83 (18)
C13—C8—C9—C10	1.7 (3)	C2—C1—S1—O1	164.30 (16)
C7—C8—C9—C10	−176.79 (18)	C6—C1—S1—O2	−136.91 (15)
C13—C8—C9—Cl1	−176.28 (14)	C2—C1—S1—O2	34.23 (18)
C7—C8—C9—Cl1	5.2 (2)	C6—C1—S1—N1	109.83 (16)
C8—C9—C10—C11	−0.3 (3)	C2—C1—S1—N1	−79.04 (17)
Cl1—C9—C10—C11	177.70 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.82 (1)	2.13 (1)	2.9465 (19)	172.(2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.82 (1)	2.13 (1)	2.9465 (19)	172 (2)

Symmetry code: (i) .