N-(3-Chloro-benzo-yl)-3-nitro-benzene-sulfonamide.

In the title compound, C(13)H(9)ClN(2)O(5)S, the dihedral angle between the two benzene rings is 83.5 (1)°. In the crystal, mol-ecules are linked via N-H⋯O(S) hydrogen bonds into helical chains running along the b axis.

Related literature

For 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. (2004 ▶), on N-(ar­yl)-methane­sulfonamides, see: Jayalakshmi & Gowda (2004 ▶), onN-(ar­yl)-aryl­sulfonamides, see: Gowda et al. (2003 ▶), on N-(substitutedbenzo­yl)-aryl­sulfonamides, see: Suchetan et al. (2011 ▶) and on N-chloro­aryl­amides, see: Gowda & Mahadevappa (1983 ▶).

Experimental

Crystal data

C13H9ClN2O5S

M = 340.73

Monoclinic,

a = 11.891 (2) Å

b = 5.0577 (6) Å

c = 23.488 (3) Å

β = 90.43 (1)°

V = 1412.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.44 mm−1

T = 293 K

0.46 × 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 = 0.822, T max = 0.957

4873 measured reflections

2840 independent reflections

2204 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.105

S = 1.20

2840 reflections

202 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.35 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/S1600536811054857/bt5758sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054857/bt5758Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811054857/bt5758Isup3.cml

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

C13H9ClN2O5S	F(000) = 696
Mr = 340.73	Dx = 1.602 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1638 reflections
a = 11.891 (2) Å	θ = 2.4–27.9°
b = 5.0577 (6) Å	µ = 0.44 mm−1
c = 23.488 (3) Å	T = 293 K
β = 90.43 (1)°	Rod, colourless
V = 1412.6 (3) Å3	0.46 × 0.20 × 0.10 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2840 independent reflections
Radiation source: fine-focus sealed tube	2204 reflections with I > 2σ(I)
graphite	Rint = 0.017
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 2.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −14→14
Tmin = 0.822, Tmax = 0.957	k = −3→6
4873 measured reflections	l = −14→29

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.20	w = 1/[σ2(Fo2) + (0.0074P)2 + 2.6391P] where P = (Fo2 + 2Fc2)/3
2840 reflections	(Δ/σ)max = 0.005
202 parameters	Δρmax = 0.35 e Å−3
1 restraint	Δρmin = −0.35 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
Cl1	−0.01505 (9)	0.2312 (2)	0.06480 (5)	0.0673 (3)
S1	0.16424 (7)	1.19021 (16)	0.25405 (3)	0.0329 (2)
O1	0.1952 (2)	1.4485 (5)	0.23632 (10)	0.0459 (6)
O2	0.06284 (18)	1.1510 (5)	0.28538 (9)	0.0426 (6)
O3	0.3210 (2)	1.0853 (6)	0.16263 (11)	0.0549 (7)
O4	0.2384 (3)	0.4415 (6)	0.40468 (13)	0.0754 (9)
O5	0.4054 (3)	0.4980 (8)	0.43876 (14)	0.0927 (12)
N1	0.1495 (2)	0.9973 (5)	0.19807 (11)	0.0326 (6)
H1N	0.099 (2)	0.888 (6)	0.2022 (14)	0.039*
N2	0.3285 (3)	0.5553 (7)	0.40604 (14)	0.0596 (10)
C1	0.2775 (3)	1.0595 (6)	0.29449 (13)	0.0329 (7)
C2	0.2570 (3)	0.8591 (7)	0.33282 (14)	0.0369 (8)
H2	0.1858	0.7855	0.3366	0.044*
C3	0.3472 (3)	0.7720 (7)	0.36558 (14)	0.0427 (9)
C4	0.4536 (3)	0.8782 (9)	0.36104 (16)	0.0529 (10)
H4	0.5124	0.8157	0.3836	0.063*
C5	0.4710 (3)	1.0782 (9)	0.32241 (17)	0.0540 (10)
H5	0.5423	1.1519	0.3189	0.065*
C6	0.3836 (3)	1.1707 (8)	0.28888 (15)	0.0436 (8)
H6	0.3957	1.3060	0.2628	0.052*
C7	0.2344 (3)	0.9602 (7)	0.15852 (14)	0.0373 (8)
C8	0.2142 (3)	0.7600 (7)	0.11301 (13)	0.0374 (8)
C9	0.1165 (3)	0.6101 (7)	0.10919 (14)	0.0399 (8)
H9	0.0580	0.6387	0.1345	0.048*
C10	0.1067 (3)	0.4200 (8)	0.06786 (14)	0.0451 (9)
C11	0.1915 (4)	0.3747 (9)	0.02952 (15)	0.0571 (11)
H11	0.1840	0.2445	0.0018	0.069*
C12	0.2877 (4)	0.5261 (9)	0.03305 (16)	0.0607 (12)
H12	0.3454	0.4976	0.0072	0.073*
C13	0.3000 (3)	0.7185 (8)	0.07404 (14)	0.0473 (9)
H13	0.3651	0.8202	0.0757	0.057*

	U11	U22	U33	U12	U13	U23
Cl1	0.0696 (7)	0.0659 (7)	0.0663 (7)	−0.0096 (6)	−0.0136 (5)	−0.0209 (6)
S1	0.0345 (4)	0.0284 (4)	0.0357 (4)	0.0021 (4)	0.0005 (3)	−0.0003 (4)
O1	0.0571 (16)	0.0278 (13)	0.0526 (15)	−0.0010 (11)	−0.0058 (12)	0.0028 (11)
O2	0.0355 (12)	0.0516 (15)	0.0408 (13)	0.0068 (11)	0.0062 (10)	−0.0020 (12)
O3	0.0418 (14)	0.0674 (18)	0.0557 (16)	−0.0170 (14)	0.0096 (12)	−0.0107 (15)
O4	0.093 (2)	0.062 (2)	0.072 (2)	0.0072 (19)	0.0132 (19)	0.0273 (18)
O5	0.104 (3)	0.108 (3)	0.066 (2)	0.040 (2)	−0.0120 (19)	0.031 (2)
N1	0.0338 (15)	0.0324 (15)	0.0318 (14)	−0.0039 (12)	0.0040 (12)	−0.0014 (12)
N2	0.081 (3)	0.058 (2)	0.0409 (18)	0.031 (2)	0.0058 (19)	0.0080 (17)
C1	0.0352 (17)	0.0316 (17)	0.0320 (16)	0.0022 (14)	0.0005 (13)	−0.0031 (15)
C2	0.0380 (18)	0.0339 (19)	0.0388 (18)	0.0029 (15)	0.0026 (14)	−0.0020 (15)
C3	0.054 (2)	0.042 (2)	0.0327 (17)	0.0148 (18)	0.0003 (15)	−0.0013 (16)
C4	0.047 (2)	0.066 (3)	0.045 (2)	0.020 (2)	−0.0072 (17)	−0.012 (2)
C5	0.0344 (19)	0.072 (3)	0.056 (2)	−0.002 (2)	−0.0006 (17)	−0.010 (2)
C6	0.0395 (19)	0.045 (2)	0.046 (2)	−0.0034 (17)	0.0036 (16)	−0.0016 (18)
C7	0.0375 (18)	0.0384 (19)	0.0360 (18)	0.0004 (16)	0.0017 (15)	0.0049 (15)
C8	0.0418 (18)	0.039 (2)	0.0313 (17)	0.0070 (16)	0.0047 (14)	0.0034 (15)
C9	0.0410 (19)	0.047 (2)	0.0314 (17)	0.0049 (17)	0.0038 (14)	−0.0014 (16)
C10	0.057 (2)	0.047 (2)	0.0319 (18)	0.0084 (18)	−0.0062 (16)	−0.0074 (17)
C11	0.077 (3)	0.060 (3)	0.035 (2)	0.014 (2)	−0.0030 (19)	−0.0113 (19)
C12	0.065 (3)	0.076 (3)	0.041 (2)	0.015 (2)	0.018 (2)	−0.005 (2)
C13	0.049 (2)	0.054 (2)	0.0388 (19)	0.0050 (19)	0.0087 (16)	0.0026 (19)

Cl1—C10	1.736 (4)	C4—C5	1.376 (6)
S1—O1	1.420 (2)	C4—H4	0.9300
S1—O2	1.431 (2)	C5—C6	1.381 (5)
S1—N1	1.645 (3)	C5—H5	0.9300
S1—C1	1.770 (3)	C6—H6	0.9300
O3—C7	1.212 (4)	C7—C8	1.490 (5)
O4—N2	1.217 (5)	C8—C9	1.390 (5)
O5—N2	1.225 (4)	C8—C13	1.391 (4)
N1—C7	1.390 (4)	C9—C10	1.371 (5)
N1—H1N	0.823 (18)	C9—H9	0.9300
N2—C3	1.468 (5)	C10—C11	1.376 (5)
C1—C2	1.378 (4)	C11—C12	1.379 (6)
C1—C6	1.388 (4)	C11—H11	0.9300
C2—C3	1.387 (5)	C12—C13	1.376 (5)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.380 (5)	C13—H13	0.9300
O1—S1—O2	119.97 (15)	C6—C5—H5	119.7
O1—S1—N1	109.70 (15)	C5—C6—C1	119.3 (4)
O2—S1—N1	104.11 (14)	C5—C6—H6	120.4
O1—S1—C1	107.63 (15)	C1—C6—H6	120.4
O2—S1—C1	108.23 (15)	O3—C7—N1	119.8 (3)
N1—S1—C1	106.45 (14)	O3—C7—C8	123.0 (3)
C7—N1—S1	122.8 (2)	N1—C7—C8	117.2 (3)
C7—N1—H1N	121 (2)	C9—C8—C13	119.5 (3)
S1—N1—H1N	112 (2)	C9—C8—C7	123.1 (3)
O4—N2—O5	123.9 (4)	C13—C8—C7	117.4 (3)
O4—N2—C3	118.2 (3)	C10—C9—C8	119.6 (3)
O5—N2—C3	117.8 (4)	C10—C9—H9	120.2
C2—C1—C6	121.7 (3)	C8—C9—H9	120.2
C2—C1—S1	119.2 (2)	C9—C10—C11	121.5 (4)
C6—C1—S1	119.1 (3)	C9—C10—Cl1	118.8 (3)
C1—C2—C3	117.2 (3)	C11—C10—Cl1	119.8 (3)
C1—C2—H2	121.4	C10—C11—C12	118.7 (4)
C3—C2—H2	121.4	C10—C11—H11	120.7
C4—C3—C2	122.6 (3)	C12—C11—H11	120.7
C4—C3—N2	118.9 (3)	C13—C12—C11	121.2 (4)
C2—C3—N2	118.5 (3)	C13—C12—H12	119.4
C5—C4—C3	118.7 (3)	C11—C12—H12	119.4
C5—C4—H4	120.7	C12—C13—C8	119.5 (4)
C3—C4—H4	120.7	C12—C13—H13	120.2
C4—C5—C6	120.6 (4)	C8—C13—H13	120.2
C4—C5—H5	119.7
O1—S1—N1—C7	55.8 (3)	C4—C5—C6—C1	0.0 (6)
O2—S1—N1—C7	−174.6 (3)	C2—C1—C6—C5	0.1 (5)
C1—S1—N1—C7	−60.4 (3)	S1—C1—C6—C5	176.8 (3)
O1—S1—C1—C2	157.3 (3)	S1—N1—C7—O3	−4.7 (5)
O2—S1—C1—C2	26.2 (3)	S1—N1—C7—C8	174.1 (2)
N1—S1—C1—C2	−85.2 (3)	O3—C7—C8—C9	177.9 (3)
O1—S1—C1—C6	−19.5 (3)	N1—C7—C8—C9	−0.8 (5)
O2—S1—C1—C6	−150.5 (3)	O3—C7—C8—C13	0.0 (5)
N1—S1—C1—C6	98.1 (3)	N1—C7—C8—C13	−178.7 (3)
C6—C1—C2—C3	−0.2 (5)	C13—C8—C9—C10	1.3 (5)
S1—C1—C2—C3	−176.9 (2)	C7—C8—C9—C10	−176.5 (3)
C1—C2—C3—C4	0.2 (5)	C8—C9—C10—C11	−0.5 (5)
C1—C2—C3—N2	−178.9 (3)	C8—C9—C10—Cl1	178.8 (3)
O4—N2—C3—C4	−171.0 (4)	C9—C10—C11—C12	−0.3 (6)
O5—N2—C3—C4	8.2 (5)	Cl1—C10—C11—C12	−179.6 (3)
O4—N2—C3—C2	8.1 (5)	C10—C11—C12—C13	0.3 (6)
O5—N2—C3—C2	−172.7 (3)	C11—C12—C13—C8	0.6 (6)
C2—C3—C4—C5	−0.1 (5)	C9—C8—C13—C12	−1.4 (5)
N2—C3—C4—C5	179.0 (3)	C7—C8—C13—C12	176.6 (3)
C3—C4—C5—C6	0.0 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.82 (2)	2.29 (2)	3.100 (3)	169 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.82 (2)	2.29 (2)	3.100 (3)	169 (3)

Symmetry code: (i) .