N-(3-Nitro-benzo-yl)benzene-sulfonamide.

In the title compound, C(13)H(10)N(2)O(5)S, the C=O bond in the -SO(2)-NH-CO- segment is anti to the meta-nitro group in the benzoyl ring, while the N-C bond has gauche torsions with respect to the S=O bonds. The molecule is twisted at the N atom with a dihedral angle of 79.9 (2)° between the sulfonyl benzene ring and the -SO(2)-NH-CO- segment. Furthermore, the dihedral angle between the benzeneline rings is 86.9 (2)°. In the structure, the mol-ecules are linked into helical chains along the b axis via N-H⋯O hydrogen bonds.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda et al. (2000 ▶, 2007 ▶), of n class="Chemical">N-(substitutedbenzo­yl)-aryl­sulfonamides, see: Gowda et al. (2009 ▶), of N-chloro­aryl­amides, see: Jyothi & Gowda (2004 ▶) and of N-bromo­aryl­sulfonamides, see: Usha & Gowda (2006 ▶).

Experimental

Crystal data

C13H10N2O5S

M = 306.29

Orthorhombic,

a = 5.1053 (5) Å

b = 13.078 (1) Å

c = 20.163 (2) Å

V = 1346.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 293 K

0.48 × 0.12 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD Detector

Absorption correction: multi-scan CrysAlis RED (Oxford Diffraction, 2009 ▶) T min = 0.884, T max = 0.969

4590 measured reflections

2282 independent reflections

1869 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.137

S = 1.38

2282 reflections

193 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.32 e Å−3

Absolute structure: Flack (1983 ▶), 871 Friedel pairs

Flack parameter: −0.1 (2)

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data n class="Disease">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/S1600536812016765/bt5879sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016765/bt5879Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812016765/bt5879Isup3.cml

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

C13H10N2O5S	F(000) = 632
Mr = 306.29	Dx = 1.511 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1855 reflections
a = 5.1053 (5) Å	θ = 3.0–27.8°
b = 13.078 (1) Å	µ = 0.26 mm−1
c = 20.163 (2) Å	T = 293 K
V = 1346.2 (2) Å3	Rod, colourless
Z = 4	0.48 × 0.12 × 0.12 mm

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD Detector	2282 independent reflections
Radiation source: fine-focus sealed tube	1869 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Rotation method data acquisition using ω and phi scans.	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan CrysAlis RED (Oxford Diffraction, 2009)	h = −3→6
Tmin = 0.884, Tmax = 0.969	k = −15→11
4590 measured reflections	l = −20→24

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)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.137	w = 1/[σ2(Fo2) + (0.P)2 + 2.6443P] where P = (Fo2 + 2Fc2)/3
S = 1.38	(Δ/σ)max < 0.001
2282 reflections	Δρmax = 0.28 e Å−3
193 parameters	Δρmin = −0.32 e Å−3
1 restraint	Absolute structure: Flack (1983), 871 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.1 (2)

Experimental. 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	0.3551 (11)	0.4936 (4)	0.9411 (3)	0.0341 (12)
C2	0.3105 (16)	0.5680 (5)	0.8942 (3)	0.0559 (18)
H2	0.1925	0.5564	0.8599	0.067*
C3	0.4420 (17)	0.6597 (5)	0.8985 (4)	0.067 (2)
H3	0.4091	0.7108	0.8675	0.080*
C4	0.6203 (16)	0.6760 (5)	0.9478 (4)	0.064 (2)
H4	0.7113	0.7375	0.9498	0.077*
C5	0.6647 (16)	0.6020 (5)	0.9941 (4)	0.067 (2)
H5	0.7854	0.6137	1.0278	0.081*
C6	0.5320 (14)	0.5097 (5)	0.9915 (3)	0.0539 (18)
H6	0.5620	0.4595	1.0233	0.065*
C7	0.4855 (12)	0.3009 (4)	0.8392 (3)	0.0362 (14)
C8	0.6560 (12)	0.2129 (4)	0.8190 (3)	0.0351 (13)
C9	0.6177 (11)	0.1146 (4)	0.8425 (3)	0.0389 (14)
H9	0.4848	0.1004	0.8727	0.047*
C10	0.7814 (13)	0.0385 (4)	0.8202 (3)	0.0398 (15)
C11	0.9833 (13)	0.0555 (5)	0.7769 (3)	0.0456 (16)
H11	1.0941	0.0026	0.7642	0.055*
C12	1.0182 (13)	0.1533 (4)	0.7527 (3)	0.0450 (16)
H12	1.1517	0.1669	0.7226	0.054*
C13	0.8550 (13)	0.2305 (5)	0.7732 (3)	0.0450 (16)
H13	0.8779	0.2960	0.7562	0.054*
N1	0.3859 (10)	0.2927 (3)	0.9027 (2)	0.0383 (12)
H1N	0.458 (11)	0.256 (4)	0.933 (2)	0.046*
N2	0.7308 (14)	−0.0663 (4)	0.8455 (3)	0.0612 (18)
O1	−0.0348 (8)	0.3898 (3)	0.8930 (2)	0.0584 (13)
O2	0.1461 (10)	0.3402 (3)	1.0022 (2)	0.0561 (13)
O3	0.4341 (9)	0.3708 (3)	0.8029 (2)	0.0504 (11)
O4	0.9051 (11)	−0.1293 (4)	0.8380 (3)	0.0777 (16)
O5	0.5233 (14)	−0.0835 (4)	0.8715 (4)	0.109 (3)
S1	0.1833 (3)	0.37784 (11)	0.93608 (8)	0.0406 (4)

	U11	U22	U33	U12	U13	U23
C1	0.036 (3)	0.026 (3)	0.040 (3)	−0.003 (2)	0.001 (3)	−0.003 (3)
C2	0.077 (5)	0.043 (4)	0.048 (4)	−0.011 (4)	−0.011 (4)	0.002 (3)
C3	0.101 (6)	0.031 (4)	0.069 (5)	−0.013 (4)	−0.007 (5)	0.012 (3)
C4	0.076 (5)	0.040 (4)	0.077 (5)	−0.016 (4)	0.000 (5)	−0.007 (4)
C5	0.064 (5)	0.060 (5)	0.077 (5)	−0.019 (4)	−0.024 (4)	−0.011 (4)
C6	0.057 (4)	0.044 (4)	0.060 (4)	0.003 (4)	−0.020 (4)	0.005 (3)
C7	0.045 (4)	0.025 (3)	0.039 (3)	−0.007 (3)	−0.008 (3)	0.001 (3)
C8	0.043 (3)	0.029 (3)	0.033 (3)	−0.004 (3)	−0.003 (3)	−0.004 (2)
C9	0.047 (4)	0.035 (3)	0.034 (3)	−0.007 (3)	0.007 (3)	−0.003 (3)
C10	0.052 (4)	0.023 (3)	0.044 (3)	−0.006 (3)	0.005 (3)	0.000 (3)
C11	0.047 (4)	0.042 (4)	0.048 (4)	0.001 (3)	0.010 (3)	−0.013 (3)
C12	0.046 (4)	0.043 (4)	0.046 (3)	−0.008 (3)	0.018 (3)	−0.003 (3)
C13	0.049 (4)	0.046 (4)	0.041 (3)	−0.016 (3)	−0.001 (3)	0.001 (3)
N1	0.047 (3)	0.027 (2)	0.041 (3)	0.007 (2)	0.000 (2)	0.005 (2)
N2	0.089 (6)	0.038 (3)	0.057 (4)	0.012 (3)	0.019 (4)	−0.002 (3)
O1	0.040 (2)	0.048 (3)	0.087 (3)	0.000 (2)	−0.012 (2)	−0.016 (3)
O2	0.074 (3)	0.038 (2)	0.056 (3)	−0.007 (2)	0.022 (3)	0.002 (2)
O3	0.065 (3)	0.040 (2)	0.046 (2)	0.005 (2)	−0.005 (2)	0.012 (2)
O4	0.111 (4)	0.047 (3)	0.074 (3)	0.029 (4)	0.020 (3)	0.007 (3)
O5	0.123 (6)	0.045 (3)	0.160 (6)	0.004 (3)	0.088 (5)	0.019 (3)
S1	0.0403 (8)	0.0314 (7)	0.0502 (8)	−0.0042 (7)	0.0052 (8)	−0.0019 (7)

C1—C2	1.376 (8)	C8—C13	1.391 (8)
C1—C6	1.376 (8)	C9—C10	1.376 (8)
C1—S1	1.753 (5)	C9—H9	0.9300
C2—C3	1.377 (9)	C10—C11	1.368 (8)
C2—H2	0.9300	C10—N2	1.485 (8)
C3—C4	1.365 (10)	C11—C12	1.381 (8)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.363 (9)	C12—C13	1.372 (8)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.386 (9)	C13—H13	0.9300
C5—H5	0.9300	N1—S1	1.662 (5)
C6—H6	0.9300	N1—H1N	0.86 (2)
C7—O3	1.200 (7)	N2—O5	1.203 (8)
C7—N1	1.382 (7)	N2—O4	1.222 (7)
C7—C8	1.499 (8)	O1—S1	1.421 (4)
C8—C9	1.385 (8)	O2—S1	1.433 (4)
C2—C1—C6	120.6 (6)	C8—C9—H9	120.9
C2—C1—S1	119.2 (5)	C11—C10—C9	123.3 (5)
C6—C1—S1	120.2 (5)	C11—C10—N2	120.0 (6)
C1—C2—C3	119.5 (6)	C9—C10—N2	116.7 (5)
C1—C2—H2	120.3	C10—C11—C12	118.2 (6)
C3—C2—H2	120.3	C10—C11—H11	120.9
C4—C3—C2	120.4 (7)	C12—C11—H11	120.9
C4—C3—H3	119.8	C13—C12—C11	119.7 (6)
C2—C3—H3	119.8	C13—C12—H12	120.1
C5—C4—C3	120.0 (7)	C11—C12—H12	120.1
C5—C4—H4	120.0	C12—C13—C8	121.5 (6)
C3—C4—H4	120.0	C12—C13—H13	119.3
C4—C5—C6	120.7 (7)	C8—C13—H13	119.3
C4—C5—H5	119.6	C7—N1—S1	123.5 (4)
C6—C5—H5	119.6	C7—N1—H1N	123 (4)
C1—C6—C5	118.8 (6)	S1—N1—H1N	111 (4)
C1—C6—H6	120.6	O5—N2—O4	124.7 (6)
C5—C6—H6	120.6	O5—N2—C10	118.4 (6)
O3—C7—N1	122.9 (6)	O4—N2—C10	116.9 (6)
O3—C7—C8	123.1 (5)	O1—S1—O2	120.2 (3)
N1—C7—C8	114.0 (5)	O1—S1—N1	108.3 (3)
C9—C8—C13	118.9 (6)	O2—S1—N1	103.2 (3)
C9—C8—C7	122.5 (5)	O1—S1—C1	109.4 (3)
C13—C8—C7	118.6 (5)	O2—S1—C1	108.0 (3)
C10—C9—C8	118.3 (5)	N1—S1—C1	106.9 (3)
C10—C9—H9	120.9
C6—C1—C2—C3	−0.9 (10)	C11—C12—C13—C8	1.0 (10)
S1—C1—C2—C3	179.0 (6)	C9—C8—C13—C12	−2.0 (9)
C1—C2—C3—C4	1.7 (12)	C7—C8—C13—C12	179.9 (5)
C2—C3—C4—C5	−1.5 (12)	O3—C7—N1—S1	0.4 (8)
C3—C4—C5—C6	0.5 (13)	C8—C7—N1—S1	−177.7 (4)
C2—C1—C6—C5	−0.1 (10)	C11—C10—N2—O5	−164.3 (7)
S1—C1—C6—C5	180.0 (6)	C9—C10—N2—O5	15.9 (10)
C4—C5—C6—C1	0.3 (12)	C11—C10—N2—O4	15.4 (9)
O3—C7—C8—C9	−147.0 (6)	C9—C10—N2—O4	−164.4 (6)
N1—C7—C8—C9	31.1 (8)	C7—N1—S1—O1	54.4 (5)
O3—C7—C8—C13	31.0 (9)	C7—N1—S1—O2	−177.2 (5)
N1—C7—C8—C13	−150.9 (5)	C7—N1—S1—C1	−63.4 (5)
C13—C8—C9—C10	0.9 (8)	C2—C1—S1—O1	−16.3 (6)
C7—C8—C9—C10	178.8 (5)	C6—C1—S1—O1	163.6 (5)
C8—C9—C10—C11	1.4 (9)	C2—C1—S1—O2	−148.7 (5)
C8—C9—C10—N2	−178.8 (5)	C6—C1—S1—O2	31.2 (6)
C9—C10—C11—C12	−2.4 (9)	C2—C1—S1—N1	100.8 (5)
N2—C10—C11—C12	177.8 (6)	C6—C1—S1—N1	−79.3 (5)
C10—C11—C12—C13	1.2 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.86 (2)	2.05 (2)	2.909 (6)	175 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.86 (2)	2.05 (2)	2.909 (6)	175 (6)

Symmetry code: (i) .