N-[(2-Chloro-phen-yl)sulfon-yl]-3-nitro-benzamide.

In the title compound, C13H9ClN2O5S, the dihedral angle between the benzene rings is 74.86 (11)°. The mol-ecule is twisted at the S atom, with a dihedral angle of 82.53 (13)° between the sulfonyl benzene ring and the S-N-C=O segment. In the crystal, mol-ecules are linked into inversion dimers through pairs of N-H⋯O hydrogen bonds, thereby forming R 2 (2)(8) loops. Mol-ecules are linked into C(7) [010] chains by weak C-H⋯O hydrogen bonds, and C-H⋯π inter-actions are also observed.

Related literature

For similar structures, see: Gowda et al. (2009 ▶, 2010 ▶); Suchetan et al. (2011 ▶, 2012 ▶).

Experimental

Crystal data

C13H9ClN2O5S

M = 340.73

Orthorhombic,

a = 12.290 (8) Å

b = 13.548 (9) Å

c = 17.240 (11) Å

V = 2870 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.44 mm−1

T = 298 K

0.32 × 0.26 × 0.18 mm

Data collection

Bruker APEXII diffractometer

22957 measured reflections

2523 independent reflections

2170 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.095

S = 1.06

2523 reflections

203 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813015912/hb7091sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813015912/hb7091Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813015912/hb7091Isup3.cml

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

C13H9ClN2O5S	Prism
Mr = 340.73	Dx = 1.577 Mg m−3
Orthorhombic, Pbca	Melting point: 483 K
Hall symbol: -P 2ac 2ab	Mo Kα radiation, λ = 0.71073 Å
a = 12.290 (8) Å	Cell parameters from 456 reflections
b = 13.548 (9) Å	θ = 2.4–25.0°
c = 17.240 (11) Å	µ = 0.44 mm−1
V = 2870 (3) Å3	T = 298 K
Z = 8	Prism, colourless
F(000) = 1392	0.32 × 0.26 × 0.18 mm

Bruker APEXII diffractometer	2170 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.059
Graphite monochromator	θmax = 25.0°, θmin = 2.4°
phi and ω scans	h = −14→14
22957 measured reflections	k = −16→16
2523 independent reflections	l = −20→20

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) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0417P)2 + 1.3036P] where P = (Fo2 + 2Fc2)/3
2523 reflections	(Δ/σ)max = 0.009
203 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
H1N1	−0.0482 (19)	0.0080 (17)	0.5829 (13)	0.038 (7)*
Cl	−0.15389 (6)	0.15122 (5)	0.47697 (4)	0.0619 (2)
O1	0.14765 (12)	0.14055 (11)	0.63851 (9)	0.0459 (4)
O2	0.08993 (13)	0.09375 (11)	0.50819 (9)	0.0417 (4)
O3	−0.04676 (15)	0.10265 (12)	0.73735 (9)	0.0500 (4)
C7	−0.06345 (17)	0.03864 (15)	0.69067 (12)	0.0360 (5)
C1	−0.01089 (17)	0.23801 (15)	0.57672 (11)	0.0326 (5)
N1	−0.02055 (16)	0.04195 (13)	0.61651 (11)	0.0372 (5)
C9	−0.10982 (18)	−0.13960 (15)	0.66930 (12)	0.0354 (5)
H9	−0.0518	−0.1458	0.6350	0.042*
C2	−0.09947 (18)	0.24942 (17)	0.52799 (12)	0.0406 (5)
C8	−0.13061 (17)	−0.05097 (15)	0.70592 (11)	0.0333 (5)
O4	−0.21793 (19)	−0.37931 (13)	0.65266 (13)	0.0796 (7)
N2	−0.15398 (19)	−0.31165 (14)	0.64382 (12)	0.0524 (6)
C3	−0.1469 (2)	0.3409 (2)	0.51955 (15)	0.0565 (7)
H3	−0.2065	0.3487	0.4868	0.068*
C12	−0.2825 (2)	−0.12449 (18)	0.77063 (14)	0.0471 (6)
H12	−0.3407	−0.1189	0.8048	0.057*
C13	−0.21677 (19)	−0.04398 (17)	0.75771 (12)	0.0427 (6)
H13	−0.2300	0.0150	0.7836	0.051*
C10	−0.17671 (19)	−0.21855 (15)	0.68463 (12)	0.0378 (5)
C5	−0.0202 (2)	0.40986 (18)	0.60766 (16)	0.0587 (7)
H5	0.0062	0.4642	0.6347	0.070*
C6	0.0285 (2)	0.31882 (16)	0.61681 (14)	0.0452 (6)
H6	0.0878	0.3119	0.6499	0.054*
O5	−0.0744 (2)	−0.31613 (14)	0.60277 (13)	0.0822 (7)
C11	−0.2639 (2)	−0.21325 (18)	0.73390 (13)	0.0443 (6)
H11	−0.3089	−0.2674	0.7423	0.053*
C4	−0.1068 (2)	0.4203 (2)	0.55921 (16)	0.0629 (8)
H4	−0.1389	0.4820	0.5530	0.076*
S1	0.06284 (4)	0.12695 (4)	0.58416 (3)	0.03356 (17)

	U11	U22	U33	U12	U13	U23
Cl	0.0569 (4)	0.0694 (5)	0.0596 (4)	−0.0047 (3)	−0.0229 (3)	−0.0149 (3)
O1	0.0407 (9)	0.0430 (9)	0.0540 (10)	−0.0002 (7)	−0.0146 (8)	0.0011 (7)
O2	0.0465 (9)	0.0391 (8)	0.0394 (9)	−0.0032 (7)	0.0112 (7)	−0.0044 (7)
O3	0.0670 (12)	0.0416 (9)	0.0415 (9)	−0.0036 (8)	0.0007 (8)	−0.0112 (8)
C7	0.0422 (12)	0.0328 (11)	0.0328 (12)	0.0053 (9)	−0.0023 (10)	−0.0001 (9)
C1	0.0361 (11)	0.0314 (11)	0.0301 (11)	−0.0002 (9)	−0.0001 (9)	0.0002 (9)
N1	0.0493 (12)	0.0319 (10)	0.0305 (10)	−0.0089 (9)	0.0011 (9)	−0.0029 (8)
C9	0.0402 (12)	0.0358 (12)	0.0301 (11)	0.0001 (9)	0.0034 (10)	0.0031 (9)
C2	0.0395 (12)	0.0466 (13)	0.0356 (12)	0.0014 (10)	−0.0034 (10)	−0.0027 (10)
C8	0.0407 (12)	0.0326 (11)	0.0267 (11)	0.0025 (9)	−0.0007 (9)	0.0039 (8)
O4	0.1089 (17)	0.0447 (11)	0.0853 (15)	−0.0325 (11)	0.0239 (13)	−0.0087 (10)
N2	0.0765 (16)	0.0340 (11)	0.0467 (12)	−0.0083 (11)	0.0071 (12)	0.0016 (9)
C3	0.0521 (16)	0.0654 (18)	0.0521 (16)	0.0171 (13)	−0.0112 (13)	0.0027 (13)
C12	0.0413 (13)	0.0607 (16)	0.0392 (13)	0.0037 (12)	0.0109 (11)	0.0101 (11)
C13	0.0540 (14)	0.0412 (12)	0.0331 (12)	0.0089 (11)	0.0054 (11)	0.0042 (10)
C10	0.0467 (13)	0.0345 (11)	0.0321 (11)	−0.0027 (10)	−0.0023 (10)	0.0030 (9)
C5	0.084 (2)	0.0343 (13)	0.0581 (17)	0.0027 (13)	−0.0037 (15)	−0.0073 (12)
C6	0.0565 (15)	0.0357 (12)	0.0433 (14)	−0.0024 (11)	−0.0087 (11)	−0.0038 (10)
O5	0.1074 (18)	0.0453 (11)	0.0940 (16)	−0.0102 (11)	0.0529 (14)	−0.0155 (10)
C11	0.0459 (14)	0.0475 (14)	0.0395 (12)	−0.0067 (11)	0.0023 (11)	0.0109 (11)
C4	0.079 (2)	0.0454 (15)	0.0646 (18)	0.0224 (14)	0.0006 (16)	0.0020 (13)
S1	0.0352 (3)	0.0302 (3)	0.0353 (3)	−0.0017 (2)	−0.0007 (2)	−0.0008 (2)

Cl—C2	1.729 (2)	O4—N2	1.217 (3)
O1—S1	1.4137 (17)	N2—O5	1.209 (3)
O2—S1	1.4243 (17)	N2—C10	1.471 (3)
O3—C7	1.201 (3)	C3—C4	1.367 (4)
C7—N1	1.384 (3)	C3—H3	0.9300
C7—C8	1.491 (3)	C12—C13	1.376 (3)
C1—C6	1.382 (3)	C12—C11	1.378 (3)
C1—C2	1.384 (3)	C12—H12	0.9300
C1—S1	1.761 (2)	C13—H13	0.9300
N1—S1	1.639 (2)	C10—C11	1.370 (3)
N1—H1N1	0.81 (2)	C5—C4	1.360 (4)
C9—C10	1.375 (3)	C5—C6	1.380 (3)
C9—C8	1.381 (3)	C5—H5	0.9300
C9—H9	0.9300	C6—H6	0.9300
C2—C3	1.378 (3)	C11—H11	0.9300
C8—C13	1.388 (3)	C4—H4	0.9300
O3—C7—N1	122.1 (2)	C11—C12—H12	119.3
O3—C7—C8	124.3 (2)	C12—C13—C8	119.9 (2)
N1—C7—C8	113.60 (18)	C12—C13—H13	120.1
C6—C1—C2	119.4 (2)	C8—C13—H13	120.1
C6—C1—S1	117.40 (17)	C11—C10—C9	123.1 (2)
C2—C1—S1	122.98 (16)	C11—C10—N2	119.4 (2)
C7—N1—S1	125.13 (16)	C9—C10—N2	117.5 (2)
C7—N1—H1N1	118.7 (16)	C4—C5—C6	120.2 (2)
S1—N1—H1N1	114.6 (16)	C4—C5—H5	119.9
C10—C9—C8	118.6 (2)	C6—C5—H5	119.9
C10—C9—H9	120.7	C5—C6—C1	119.9 (2)
C8—C9—H9	120.7	C5—C6—H6	120.0
C3—C2—C1	119.8 (2)	C1—C6—H6	120.0
C3—C2—Cl	118.35 (19)	C10—C11—C12	117.4 (2)
C1—C2—Cl	121.81 (17)	C10—C11—H11	121.3
C9—C8—C13	119.6 (2)	C12—C11—H11	121.3
C9—C8—C7	121.66 (19)	C5—C4—C3	120.5 (2)
C13—C8—C7	118.69 (19)	C5—C4—H4	119.7
O5—N2—O4	123.9 (2)	C3—C4—H4	119.7
O5—N2—C10	118.5 (2)	O1—S1—O2	118.58 (11)
O4—N2—C10	117.6 (2)	O1—S1—N1	109.09 (10)
C4—C3—C2	120.2 (2)	O2—S1—N1	103.72 (10)
C4—C3—H3	119.9	O1—S1—C1	108.43 (10)
C2—C3—H3	119.9	O2—S1—C1	108.86 (10)
C13—C12—C11	121.3 (2)	N1—S1—C1	107.65 (11)
C13—C12—H12	119.3
O3—C7—N1—S1	4.0 (3)	O4—N2—C10—C11	3.8 (3)
C8—C7—N1—S1	−175.78 (15)	O5—N2—C10—C9	4.4 (3)
C6—C1—C2—C3	0.4 (3)	O4—N2—C10—C9	−174.4 (2)
S1—C1—C2—C3	−173.82 (19)	C4—C5—C6—C1	−0.1 (4)
C6—C1—C2—Cl	−179.23 (18)	C2—C1—C6—C5	−0.3 (3)
S1—C1—C2—Cl	6.5 (3)	S1—C1—C6—C5	174.2 (2)
C10—C9—C8—C13	0.9 (3)	C9—C10—C11—C12	−1.6 (3)
C10—C9—C8—C7	−178.37 (19)	N2—C10—C11—C12	−179.7 (2)
O3—C7—C8—C9	−149.7 (2)	C13—C12—C11—C10	0.7 (3)
N1—C7—C8—C9	30.1 (3)	C6—C5—C4—C3	0.5 (4)
O3—C7—C8—C13	31.0 (3)	C2—C3—C4—C5	−0.4 (4)
N1—C7—C8—C13	−149.2 (2)	C7—N1—S1—O1	48.2 (2)
C1—C2—C3—C4	0.0 (4)	C7—N1—S1—O2	175.44 (18)
Cl—C2—C3—C4	179.6 (2)	C7—N1—S1—C1	−69.3 (2)
C11—C12—C13—C8	0.9 (4)	C6—C1—S1—O1	5.5 (2)
C9—C8—C13—C12	−1.7 (3)	C2—C1—S1—O1	179.83 (18)
C7—C8—C13—C12	177.6 (2)	C6—C1—S1—O2	−124.79 (18)
C8—C9—C10—C11	0.8 (3)	C2—C1—S1—O2	49.5 (2)
C8—C9—C10—N2	178.95 (19)	C6—C1—S1—N1	123.40 (18)
O5—N2—C10—C11	−177.3 (2)	C2—C1—S1—N1	−62.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2i	0.81 (2)	2.15 (2)	2.954 (3)	169 (2)
C11—H11···O3ii	0.93	2.50	3.411 (3)	166
C6—H6···Cgiii	0.93	2.72	3.550 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the nitro­benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2i	0.81 (2)	2.15 (2)	2.954 (3)	169 (2)
C11—H11⋯O3ii	0.93	2.50	3.411 (3)	166
C6—H6⋯Cg iii	0.93	2.72	3.550 (3)	150

Symmetry codes: (i) ; (ii) ; (iii) .