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

In the title compound, C(13)H(9)ClN(2)O(5)S, the N-H bond is trans to the C=O bond. The dihedral angle between the two aromatic rings is 85.4 (1)°. In the crystal, mol-ecules are linked into zigzag C(4) chains along the b axis through N-H⋯O hydrogen bonds.

Related literature

For our study of the effect of substituents on the structures of N-(ar­yl)-amides, see: Gowda et al. (2000 ▶), of N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶) and of N-(p-substituted-benzo­yl)-p-substituted-benzene­sulfonamides, see: Gowda et al. (2010 ▶); Suchetan et al. (2011 ▶).

Experimental

Crystal data

C13H9ClN2O5S

M = 340.73

Monoclinic,

a = 11.097 (2) Å

b = 5.3063 (7) Å

c = 12.319 (2) Å

β = 104.24 (2)°

V = 703.10 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.45 mm−1

T = 293 K

0.48 × 0.16 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.815, T max = 0.949

2641 measured reflections

2213 independent reflections

2072 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.087

S = 1.06

2213 reflections

202 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.38 e Å−3

Absolute structure: Flack (1983 ▶), 607 Friedel pairs

Flack parameter: 0.05 (8)

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; 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 datablocks I, global. DOI: 10.1107/S1600536811009913/bt5494sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009913/bt5494Isup2.hkl

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

C13H9ClN2O5S	F(000) = 348
Mr = 340.73	Dx = 1.609 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1433 reflections
a = 11.097 (2) Å	θ = 2.9–27.8°
b = 5.3063 (7) Å	µ = 0.45 mm−1
c = 12.319 (2) Å	T = 293 K
β = 104.24 (2)°	Rod, colourless
V = 703.10 (19) Å3	0.48 × 0.16 × 0.12 mm
Z = 2

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2213 independent reflections
Radiation source: fine-focus sealed tube	2072 reflections with I > 2σ(I)
graphite	Rint = 0.016
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→8
Tmin = 0.815, Tmax = 0.949	k = −5→6
2641 measured reflections	l = −15→15

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)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087	w = 1/[σ2(Fo2) + (0.052P)2 + 0.2456P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2213 reflections	Δρmax = 0.23 e Å−3
202 parameters	Δρmin = −0.38 e Å−3
2 restraints	Absolute structure: Flack (1983), 607 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.05 (8)

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
Cl1	0.24217 (8)	0.24133 (17)	−0.03446 (7)	0.0518 (2)
S1	0.40651 (6)	−0.22075 (13)	0.11243 (5)	0.02944 (16)
O1	0.40724 (17)	−0.2097 (5)	−0.00329 (14)	0.0383 (5)
O2	0.4343 (2)	−0.4512 (4)	0.17156 (18)	0.0423 (5)
O3	0.4791 (2)	−0.0713 (5)	0.34556 (16)	0.0495 (6)
O4	0.9366 (2)	0.9181 (5)	0.4214 (2)	0.0607 (7)
O5	0.8756 (3)	0.8856 (6)	0.5731 (2)	0.0675 (8)
N1	0.5096 (2)	−0.0071 (5)	0.17282 (18)	0.0300 (5)
H1N	0.528 (3)	0.097 (5)	0.127 (2)	0.036*
N2	0.8742 (2)	0.8214 (5)	0.4779 (2)	0.0435 (6)
C1	0.2624 (2)	−0.1120 (5)	0.1320 (2)	0.0308 (6)
C2	0.1961 (3)	0.0885 (6)	0.0729 (2)	0.0352 (6)
C3	0.0884 (3)	0.1720 (7)	0.0994 (3)	0.0497 (8)
H3	0.0442	0.3070	0.0608	0.060*
C4	0.0468 (3)	0.0537 (9)	0.1834 (3)	0.0551 (10)
H4	−0.0251	0.1111	0.2013	0.066*
C5	0.1098 (3)	−0.1457 (8)	0.2402 (3)	0.0543 (10)
H5	0.0800	−0.2257	0.2955	0.065*
C6	0.2182 (3)	−0.2287 (8)	0.2153 (2)	0.0423 (7)
H6	0.2616	−0.3635	0.2547	0.051*
C7	0.5325 (2)	0.0433 (6)	0.2870 (2)	0.0323 (6)
C8	0.6273 (2)	0.2411 (6)	0.3335 (2)	0.0319 (6)
C9	0.6257 (3)	0.3356 (7)	0.4375 (2)	0.0416 (8)
H9	0.5698	0.2706	0.4755	0.050*
C10	0.7064 (3)	0.5262 (7)	0.4858 (2)	0.0429 (8)
H10	0.7047	0.5926	0.5552	0.052*
C11	0.7893 (3)	0.6146 (6)	0.4280 (2)	0.0366 (7)
C12	0.7948 (3)	0.5216 (7)	0.3252 (2)	0.0432 (8)
H12	0.8525	0.5835	0.2885	0.052*
C13	0.7121 (3)	0.3329 (7)	0.2776 (2)	0.0399 (8)
H13	0.7137	0.2678	0.2079	0.048*

	U11	U22	U33	U12	U13	U23
Cl1	0.0584 (5)	0.0462 (5)	0.0490 (4)	0.0055 (4)	0.0095 (3)	0.0178 (4)
S1	0.0344 (3)	0.0269 (3)	0.0271 (3)	0.0019 (3)	0.0077 (2)	−0.0002 (3)
O1	0.0459 (11)	0.0410 (12)	0.0292 (9)	0.0005 (11)	0.0119 (8)	−0.0070 (10)
O2	0.0515 (13)	0.0307 (12)	0.0448 (12)	0.0056 (10)	0.0118 (10)	0.0043 (10)
O3	0.0589 (14)	0.0627 (17)	0.0287 (10)	−0.0198 (12)	0.0145 (9)	−0.0008 (11)
O4	0.0569 (15)	0.0591 (17)	0.0662 (16)	−0.0189 (13)	0.0157 (13)	−0.0034 (14)
O5	0.0776 (18)	0.069 (2)	0.0533 (15)	−0.0174 (16)	0.0117 (13)	−0.0253 (14)
N1	0.0318 (12)	0.0338 (14)	0.0246 (11)	−0.0045 (10)	0.0071 (9)	0.0005 (10)
N2	0.0382 (13)	0.0413 (17)	0.0470 (14)	0.0011 (12)	0.0025 (11)	−0.0015 (13)
C1	0.0294 (13)	0.0312 (15)	0.0301 (13)	−0.0006 (12)	0.0040 (10)	−0.0053 (12)
C2	0.0326 (14)	0.0354 (16)	0.0343 (14)	−0.0034 (12)	0.0019 (11)	−0.0037 (13)
C3	0.0350 (16)	0.050 (2)	0.059 (2)	0.0079 (15)	0.0018 (14)	−0.0061 (17)
C4	0.0352 (17)	0.073 (3)	0.059 (2)	0.0004 (18)	0.0166 (15)	−0.016 (2)
C5	0.0476 (19)	0.071 (3)	0.0496 (18)	−0.0089 (18)	0.0217 (15)	−0.0027 (18)
C6	0.0429 (15)	0.0456 (17)	0.0392 (14)	−0.0023 (17)	0.0119 (11)	0.0049 (18)
C7	0.0304 (14)	0.0413 (17)	0.0253 (12)	0.0017 (13)	0.0071 (10)	0.0036 (12)
C8	0.0270 (12)	0.0413 (18)	0.0244 (11)	0.0015 (13)	0.0007 (9)	0.0043 (13)
C9	0.0421 (16)	0.053 (2)	0.0318 (13)	−0.0083 (14)	0.0129 (12)	−0.0023 (14)
C10	0.0453 (18)	0.055 (2)	0.0290 (14)	−0.0057 (16)	0.0106 (12)	−0.0090 (15)
C11	0.0304 (14)	0.0410 (18)	0.0353 (15)	0.0030 (13)	0.0024 (11)	−0.0017 (13)
C12	0.0347 (16)	0.061 (2)	0.0340 (14)	−0.0082 (15)	0.0083 (12)	0.0007 (16)
C13	0.0363 (14)	0.058 (2)	0.0269 (12)	−0.0073 (14)	0.0100 (11)	−0.0067 (14)

Cl1—C2	1.732 (3)	C4—C5	1.363 (5)
S1—O2	1.418 (2)	C4—H4	0.9300
S1—O1	1.4287 (18)	C5—C6	1.384 (4)
S1—N1	1.652 (2)	C5—H5	0.9300
S1—C1	1.771 (3)	C6—H6	0.9300
O3—C7	1.205 (3)	C7—C8	1.497 (4)
O4—N2	1.210 (3)	C8—C9	1.381 (4)
O5—N2	1.219 (3)	C8—C13	1.383 (4)
N1—C7	1.392 (3)	C9—C10	1.385 (4)
N1—H1N	0.849 (18)	C9—H9	0.9300
N2—C11	1.478 (4)	C10—C11	1.376 (4)
C1—C6	1.387 (4)	C10—H10	0.9300
C1—C2	1.393 (4)	C11—C12	1.375 (4)
C2—C3	1.387 (4)	C12—C13	1.387 (4)
C3—C4	1.382 (5)	C12—H12	0.9300
C3—H3	0.9300	C13—H13	0.9300
O2—S1—O1	119.61 (14)	C6—C5—H5	120.1
O2—S1—N1	108.76 (13)	C5—C6—C1	120.5 (3)
O1—S1—N1	104.36 (12)	C5—C6—H6	119.8
O2—S1—C1	107.47 (13)	C1—C6—H6	119.8
O1—S1—C1	110.47 (12)	O3—C7—N1	120.9 (3)
N1—S1—C1	105.25 (13)	O3—C7—C8	121.9 (2)
C7—N1—S1	121.41 (19)	N1—C7—C8	117.2 (2)
C7—N1—H1N	122 (2)	C9—C8—C13	120.0 (3)
S1—N1—H1N	114 (2)	C9—C8—C7	116.2 (2)
O4—N2—O5	124.2 (3)	C13—C8—C7	123.8 (2)
O4—N2—C11	118.2 (3)	C8—C9—C10	120.6 (3)
O5—N2—C11	117.6 (3)	C8—C9—H9	119.7
C6—C1—C2	119.3 (3)	C10—C9—H9	119.7
C6—C1—S1	116.8 (2)	C11—C10—C9	118.1 (3)
C2—C1—S1	123.8 (2)	C11—C10—H10	120.9
C3—C2—C1	119.7 (3)	C9—C10—H10	120.9
C3—C2—Cl1	117.6 (3)	C12—C11—C10	122.8 (3)
C1—C2—Cl1	122.7 (2)	C12—C11—N2	118.7 (3)
C4—C3—C2	119.8 (3)	C10—C11—N2	118.5 (3)
C4—C3—H3	120.1	C11—C12—C13	118.2 (3)
C2—C3—H3	120.1	C11—C12—H12	120.9
C5—C4—C3	120.9 (3)	C13—C12—H12	120.9
C5—C4—H4	119.5	C8—C13—C12	120.3 (3)
C3—C4—H4	119.5	C8—C13—H13	119.8
C4—C5—C6	119.8 (3)	C12—C13—H13	119.8
C4—C5—H5	120.1
O2—S1—N1—C7	−53.2 (3)	S1—N1—C7—O3	1.3 (4)
O1—S1—N1—C7	178.0 (2)	S1—N1—C7—C8	−179.8 (2)
C1—S1—N1—C7	61.7 (2)	O3—C7—C8—C9	−17.6 (4)
O2—S1—C1—C6	13.3 (3)	N1—C7—C8—C9	163.4 (3)
O1—S1—C1—C6	145.4 (2)	O3—C7—C8—C13	163.5 (3)
N1—S1—C1—C6	−102.5 (2)	N1—C7—C8—C13	−15.4 (4)
O2—S1—C1—C2	−169.9 (2)	C13—C8—C9—C10	1.5 (5)
O1—S1—C1—C2	−37.8 (3)	C7—C8—C9—C10	−177.4 (3)
N1—S1—C1—C2	74.3 (3)	C8—C9—C10—C11	−1.1 (5)
C6—C1—C2—C3	1.3 (4)	C9—C10—C11—C12	0.0 (5)
S1—C1—C2—C3	−175.5 (2)	C9—C10—C11—N2	178.9 (3)
C6—C1—C2—Cl1	−178.5 (2)	O4—N2—C11—C12	7.4 (4)
S1—C1—C2—Cl1	4.7 (4)	O5—N2—C11—C12	−173.6 (3)
C1—C2—C3—C4	−0.7 (5)	O4—N2—C11—C10	−171.6 (3)
Cl1—C2—C3—C4	179.1 (3)	O5—N2—C11—C10	7.5 (4)
C2—C3—C4—C5	−0.5 (6)	C10—C11—C12—C13	0.8 (5)
C3—C4—C5—C6	1.3 (6)	N2—C11—C12—C13	−178.1 (3)
C4—C5—C6—C1	−0.7 (5)	C9—C8—C13—C12	−0.7 (5)
C2—C1—C6—C5	−0.5 (4)	C7—C8—C13—C12	178.2 (3)
S1—C1—C6—C5	176.4 (3)	C11—C12—C13—C8	−0.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.85 (2)	2.11 (2)	2.941 (3)	168 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.85 (2)	2.11 (2)	2.941 (3)	168 (3)

Symmetry code: (i) .