N-Benzoyl-2-nitro-benzene-sulfonamide.

In the title compound, C(13)H(10)N(2)O(5)S, the N-C bond in the C-SO(2)-NH-C segment has gauche torsion angles with respect to the S=O bonds. The conformation between the N-H bond and the ortho-nitro group in the sulfonyl benzene ring is syn. The mol-ecule is twisted at the S-N bond with a torsion angle of -63.4 (2)°. The sulfonyl benzene ring is tilted by 77.1 (1)° relative to the -SO(2)-NH-C-O segment. The dihedral angle between the sulfonyl and the benzoyl benzene rings is 88.6 (1)°. In the crystal, pairs of N-H⋯O(S) hydrogen bonds link the mol-ecules into inversion dimers, which are linked by weak C-H⋯O and C-H⋯π inter-actions along the b axis.

Related literature

For studies, including those by our group, 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: Jayalakshmi & Gowda (2004 ▶), on N-(ar­yl)-aryl­sulfonamides, see: Gowda et al. (2003 ▶), on N-(substitutedbenzo­yl)-aryl­sulfonamides, see: Suchetan et al. (2010 ▶) and on N-chloro­aryl­amides, see: Gowda & Maha­de­vappa (1983 ▶).

Experimental

Crystal data

C13H10N2O5S

M = 306.29

Orthorhombic,

a = 12.1127 (8) Å

b = 11.7625 (8) Å

c = 18.730 (1) Å

V = 2668.6 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.27 mm−1

T = 293 K

0.48 × 0.44 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.883, T max = 0.901

6396 measured reflections

2711 independent reflections

2010 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.110

S = 1.04

2711 reflections

193 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.36 e Å−3

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 datablock(s) I, global. DOI: 10.1107/S1600536811055917/bq2330sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055917/bq2330Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811055917/bq2330Isup3.cml

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

C13H10N2O5S	F(000) = 1264
Mr = 306.29	Dx = 1.525 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2597 reflections
a = 12.1127 (8) Å	θ = 2.6–27.8°
b = 11.7625 (8) Å	µ = 0.27 mm−1
c = 18.730 (1) Å	T = 293 K
V = 2668.6 (3) Å3	Prism, colorless
Z = 8	0.48 × 0.44 × 0.40 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2711 independent reflections
Radiation source: fine-focus sealed tube	2010 reflections with I > 2σ(I)
graphite	Rint = 0.020
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→15
Tmin = 0.883, Tmax = 0.901	k = −14→14
6396 measured reflections	l = −14→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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0388P)2 + 2.8009P] where P = (Fo2 + 2Fc2)/3
2711 reflections	(Δ/σ)max = 0.001
193 parameters	Δρmax = 0.31 e Å−3
1 restraint	Δρmin = −0.36 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	1.01092 (19)	0.2867 (2)	0.42850 (12)	0.0320 (5)
C2	1.08964 (19)	0.3142 (2)	0.47986 (13)	0.0352 (5)
C3	1.1400 (2)	0.4186 (2)	0.48146 (15)	0.0458 (6)
H3	1.1912	0.4360	0.5168	0.055*
C4	1.1134 (2)	0.4975 (2)	0.42959 (15)	0.0503 (7)
H4	1.1473	0.5684	0.4298	0.060*
C5	1.0369 (2)	0.4717 (2)	0.37750 (15)	0.0496 (7)
H5	1.0201	0.5249	0.3424	0.060*
C6	0.9851 (2)	0.3670 (2)	0.37733 (14)	0.0413 (6)
H6	0.9326	0.3505	0.3426	0.050*
C7	1.0522 (2)	0.0708 (2)	0.31993 (13)	0.0344 (5)
C8	1.13311 (19)	−0.01632 (19)	0.29607 (12)	0.0332 (5)
C9	1.2011 (2)	0.0112 (2)	0.23910 (13)	0.0400 (6)
H9	1.1942	0.0816	0.2170	0.048*
C10	1.2786 (2)	−0.0652 (2)	0.21516 (14)	0.0436 (6)
H10	1.3247	−0.0458	0.1773	0.052*
C11	1.2882 (2)	−0.1697 (2)	0.24688 (14)	0.0482 (7)
H11	1.3412	−0.2209	0.2309	0.058*
C12	1.2194 (3)	−0.1986 (2)	0.30227 (16)	0.0589 (8)
H12	1.2252	−0.2701	0.3231	0.071*
C13	1.1419 (2)	−0.1227 (2)	0.32734 (14)	0.0482 (7)
H13	1.0959	−0.1428	0.3650	0.058*
N1	1.01881 (17)	0.06273 (17)	0.39120 (11)	0.0355 (5)
H1N	1.051 (2)	0.021 (2)	0.4206 (12)	0.043*
N2	1.12183 (18)	0.2319 (2)	0.53570 (13)	0.0467 (6)
O1	0.84056 (14)	0.17061 (15)	0.38774 (10)	0.0455 (5)
O2	0.92831 (15)	0.11935 (15)	0.50171 (9)	0.0418 (4)
O3	1.01759 (16)	0.14595 (15)	0.28213 (9)	0.0468 (5)
O4	1.09678 (19)	0.2545 (2)	0.59685 (11)	0.0660 (6)
O5	1.1726 (2)	0.14835 (19)	0.51681 (13)	0.0695 (6)
S1	0.93749 (5)	0.15669 (5)	0.42926 (3)	0.03293 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0320 (11)	0.0317 (12)	0.0323 (12)	0.0037 (10)	0.0015 (10)	0.0001 (10)
C2	0.0327 (12)	0.0375 (13)	0.0355 (12)	0.0042 (10)	−0.0013 (10)	0.0035 (10)
C3	0.0393 (14)	0.0489 (16)	0.0492 (15)	−0.0016 (13)	−0.0060 (12)	−0.0019 (13)
C4	0.0541 (16)	0.0358 (14)	0.0612 (17)	−0.0060 (13)	0.0042 (15)	0.0024 (13)
C5	0.0635 (18)	0.0386 (15)	0.0468 (15)	0.0050 (14)	−0.0012 (14)	0.0098 (12)
C6	0.0469 (14)	0.0410 (14)	0.0360 (13)	0.0046 (12)	−0.0051 (12)	0.0010 (11)
C7	0.0372 (13)	0.0313 (12)	0.0347 (12)	−0.0031 (11)	0.0015 (11)	−0.0029 (10)
C8	0.0365 (12)	0.0312 (12)	0.0317 (12)	−0.0033 (11)	0.0017 (10)	−0.0058 (10)
C9	0.0483 (14)	0.0309 (12)	0.0408 (14)	−0.0057 (11)	0.0069 (12)	−0.0018 (11)
C10	0.0445 (15)	0.0418 (14)	0.0444 (14)	−0.0036 (12)	0.0145 (12)	−0.0040 (12)
C11	0.0536 (16)	0.0444 (15)	0.0465 (15)	0.0130 (13)	0.0086 (13)	−0.0081 (13)
C12	0.087 (2)	0.0385 (15)	0.0512 (16)	0.0179 (16)	0.0180 (16)	0.0066 (13)
C13	0.0654 (18)	0.0397 (14)	0.0395 (14)	0.0059 (14)	0.0193 (13)	0.0026 (12)
N1	0.0412 (12)	0.0330 (11)	0.0324 (11)	0.0076 (9)	0.0019 (9)	0.0004 (9)
N2	0.0417 (12)	0.0494 (14)	0.0490 (14)	0.0001 (11)	−0.0116 (11)	0.0062 (11)
O1	0.0335 (9)	0.0494 (11)	0.0535 (11)	0.0024 (8)	−0.0053 (8)	−0.0030 (9)
O2	0.0489 (10)	0.0402 (10)	0.0361 (9)	0.0012 (8)	0.0105 (8)	0.0004 (8)
O3	0.0561 (11)	0.0424 (10)	0.0420 (10)	0.0097 (9)	0.0068 (9)	0.0063 (9)
O4	0.0764 (15)	0.0815 (16)	0.0400 (12)	−0.0017 (13)	−0.0101 (11)	0.0097 (11)
O5	0.0756 (15)	0.0536 (13)	0.0794 (15)	0.0219 (12)	−0.0179 (13)	0.0069 (12)
S1	0.0321 (3)	0.0332 (3)	0.0335 (3)	0.0027 (3)	0.0028 (3)	−0.0015 (2)

C1—C6	1.381 (3)	C8—C13	1.386 (3)
C1—C2	1.392 (3)	C9—C10	1.375 (3)
C1—S1	1.769 (2)	C9—H9	0.9300
C2—C3	1.372 (4)	C10—C11	1.370 (4)
C2—N2	1.477 (3)	C10—H10	0.9300
C3—C4	1.382 (4)	C11—C12	1.374 (4)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.379 (4)	C12—C13	1.377 (4)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.382 (4)	C13—H13	0.9300
C5—H5	0.9300	N1—S1	1.643 (2)
C6—H6	0.9300	N1—H1N	0.835 (17)
C7—O3	1.207 (3)	N2—O5	1.211 (3)
C7—N1	1.398 (3)	N2—O4	1.214 (3)
C7—C8	1.487 (3)	O1—S1	1.4177 (18)
C8—C9	1.386 (3)	O2—S1	1.4308 (17)
C6—C1—C2	118.4 (2)	C8—C9—H9	119.8
C6—C1—S1	118.86 (19)	C11—C10—C9	120.2 (2)
C2—C1—S1	122.61 (18)	C11—C10—H10	119.9
C3—C2—C1	121.8 (2)	C9—C10—H10	119.9
C3—C2—N2	117.0 (2)	C10—C11—C12	119.9 (2)
C1—C2—N2	121.2 (2)	C10—C11—H11	120.1
C2—C3—C4	118.8 (3)	C12—C11—H11	120.1
C2—C3—H3	120.6	C11—C12—C13	120.7 (3)
C4—C3—H3	120.6	C11—C12—H12	119.7
C5—C4—C3	120.4 (3)	C13—C12—H12	119.7
C5—C4—H4	119.8	C12—C13—C8	119.6 (2)
C3—C4—H4	119.8	C12—C13—H13	120.2
C4—C5—C6	120.2 (3)	C8—C13—H13	120.2
C4—C5—H5	119.9	C7—N1—S1	122.79 (17)
C6—C5—H5	119.9	C7—N1—H1N	122.4 (18)
C1—C6—C5	120.3 (2)	S1—N1—H1N	112.9 (18)
C1—C6—H6	119.8	O5—N2—O4	125.5 (2)
C5—C6—H6	119.8	O5—N2—C2	117.3 (2)
O3—C7—N1	120.7 (2)	O4—N2—C2	117.3 (2)
O3—C7—C8	123.8 (2)	O1—S1—O2	119.43 (11)
N1—C7—C8	115.5 (2)	O1—S1—N1	109.64 (11)
C9—C8—C13	119.4 (2)	O2—S1—N1	104.57 (10)
C9—C8—C7	117.5 (2)	O1—S1—C1	108.18 (11)
C13—C8—C7	123.1 (2)	O2—S1—C1	108.18 (11)
C10—C9—C8	120.3 (2)	N1—S1—C1	106.06 (11)
C10—C9—H9	119.8
C6—C1—C2—C3	1.2 (4)	C10—C11—C12—C13	−1.2 (5)
S1—C1—C2—C3	−175.2 (2)	C11—C12—C13—C8	0.3 (5)
C6—C1—C2—N2	−179.4 (2)	C9—C8—C13—C12	1.2 (4)
S1—C1—C2—N2	4.2 (3)	C7—C8—C13—C12	−179.8 (3)
C1—C2—C3—C4	−1.5 (4)	O3—C7—N1—S1	−3.5 (3)
N2—C2—C3—C4	179.1 (2)	C8—C7—N1—S1	175.16 (16)
C2—C3—C4—C5	0.4 (4)	C3—C2—N2—O5	−112.1 (3)
C3—C4—C5—C6	0.8 (4)	C1—C2—N2—O5	68.4 (3)
C2—C1—C6—C5	0.1 (4)	C3—C2—N2—O4	66.7 (3)
S1—C1—C6—C5	176.7 (2)	C1—C2—N2—O4	−112.7 (3)
C4—C5—C6—C1	−1.1 (4)	C7—N1—S1—O1	53.2 (2)
O3—C7—C8—C9	23.9 (4)	C7—N1—S1—O2	−177.62 (19)
N1—C7—C8—C9	−154.7 (2)	C7—N1—S1—C1	−63.4 (2)
O3—C7—C8—C13	−155.1 (3)	C6—C1—S1—O1	−16.5 (2)
N1—C7—C8—C13	26.2 (3)	C2—C1—S1—O1	159.83 (19)
C13—C8—C9—C10	−1.8 (4)	C6—C1—S1—O2	−147.3 (2)
C7—C8—C9—C10	179.1 (2)	C2—C1—S1—O2	29.1 (2)
C8—C9—C10—C11	0.9 (4)	C6—C1—S1—N1	101.0 (2)
C9—C10—C11—C12	0.7 (4)	C2—C1—S1—N1	−82.6 (2)

Cg1 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.84 (2)	2.21 (2)	3.003 (3)	158 (2)
C11—H11···O3ii	0.93	2.51	3.267 (3)	139
C13—H13···O2i	0.93	2.53	3.313 (3)	142
C6—H6···Cg1iii	0.93	2.82	3.678 (13)	153

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.84 (2)	2.21 (2)	3.003 (3)	158 (2)
C11—H11⋯O3ii	0.93	2.51	3.267 (3)	139
C13—H13⋯O2i	0.93	2.53	3.313 (3)	142
C6—H6⋯Cg1iii	0.93	2.82	3.678 (13)	153

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