N-(3-Methyl-benzo-yl)-2-nitro-benzene-sulfonamide.

In the title compound, C(14)H(12)N(2)O(5)S, the conformation between the N-H group and the ortho-nitro group in the sulfonyl benzene ring is syn and that between the C=O and meta-methyl groups in the benzoyl ring is anti. The mol-ecule is twisted at the S-N bond with a torsion angle of 64.3 (2)°. The dihedral angle between the sulfonyl benzene ring and the -SO(2)-NH-C-O segment is 75.73 (7)° and that between the sulfonyl and benzoyl benzene rings is 89.5 (1)°. The crystal structure features inversion-related dimers linked by pairs of N-H⋯O(S) hydrogen bonds.

Related literature

For studies, including 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. (1999 ▶, 2003 ▶), on n class="Chemical">N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶), on N-(ar­yl)-aryl­sulfonamides, see: Shetty & Gowda (2005 ▶), on N-(substitutedbenzo­yl)-aryl­sulfonamides, see: Suchetan et al. (2012 ▶), on N-chloro­aryl­amides, see: Jyothi & Gowda (2004 ▶) and on N-bromo­aryl­sulfonamides, see: Usha & Gowda (2006 ▶).

Experimental

Crystal data

C14H12N2O5S

M = 320.32

Orthorhombic,

a = 12.227 (1) Å

b = 12.854 (1) Å

c = 18.317 (2) Å

V = 2878.8 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.48 × 0.44 × 0.32 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.889, T max = 0.924

7423 measured reflections

2936 independent reflections

2306 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.124

S = 1.04

2936 reflections

203 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.33 e Å−3

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/S160053681200164X/bq2333sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200164X/bq2333Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681200164X/bq2333Isup3.cml

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

C14H12N2O5S	F(000) = 1328
Mr = 320.32	Dx = 1.478 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2012 reflections
a = 12.227 (1) Å	θ = 2.6–27.8°
b = 12.854 (1) Å	µ = 0.25 mm−1
c = 18.317 (2) Å	T = 293 K
V = 2878.8 (5) Å3	Prism, colorless
Z = 8	0.48 × 0.44 × 0.32 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2936 independent reflections
Radiation source: fine-focus sealed tube	2306 reflections with I > 2σ(I)
graphite	Rint = 0.019
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −15→8
Tmin = 0.889, Tmax = 0.924	k = −8→16
7423 measured reflections	l = −21→22

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0579P)2 + 1.5722P] where P = (Fo2 + 2Fc2)/3
2936 reflections	(Δ/σ)max = 0.001
203 parameters	Δρmax = 0.38 e Å−3
1 restraint	Δρmin = −0.33 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	−0.01166 (16)	0.27278 (16)	0.42995 (11)	0.0350 (5)
C2	−0.08805 (18)	0.29514 (18)	0.48387 (12)	0.0388 (5)
C3	−0.1383 (2)	0.3902 (2)	0.48790 (14)	0.0527 (6)
H3	−0.1875	0.4044	0.5253	0.063*
C4	−0.1152 (2)	0.4641 (2)	0.43633 (15)	0.0570 (7)
H4	−0.1501	0.5283	0.4381	0.068*
C5	−0.0406 (2)	0.4437 (2)	0.38192 (15)	0.0555 (7)
H5	−0.0253	0.4942	0.3470	0.067*
C6	0.0114 (2)	0.34880 (18)	0.37891 (13)	0.0458 (6)
H6	0.0624	0.3358	0.3423	0.055*
C7	−0.04990 (18)	0.07627 (17)	0.31441 (11)	0.0374 (5)
C8	−0.12208 (17)	−0.00987 (17)	0.29044 (11)	0.0360 (5)
C9	−0.12101 (18)	−0.10611 (17)	0.32424 (11)	0.0382 (5)
H9	−0.0711	−0.1183	0.3616	0.046*
C10	−0.19217 (19)	−0.18475 (18)	0.30397 (12)	0.0410 (5)
C11	−0.2658 (2)	−0.16427 (19)	0.24824 (13)	0.0478 (6)
H11	−0.3160	−0.2150	0.2345	0.057*
C12	−0.2657 (2)	−0.0692 (2)	0.21280 (13)	0.0508 (6)
H12	−0.3144	−0.0575	0.1747	0.061*
C13	−0.19427 (19)	0.00806 (19)	0.23328 (12)	0.0439 (5)
H13	−0.1943	0.0717	0.2091	0.053*
C14	−0.1881 (2)	−0.2872 (2)	0.34183 (15)	0.0585 (7)
H14A	−0.1384	−0.2832	0.3823	0.070*
H14B	−0.1636	−0.3397	0.3083	0.070*
H14C	−0.2598	−0.3048	0.3593	0.070*
N1	−0.01587 (16)	0.06904 (15)	0.38733 (10)	0.0396 (4)
H1N	−0.0492 (18)	0.0295 (18)	0.4169 (12)	0.048*
N2	−0.11943 (17)	0.21727 (18)	0.53943 (12)	0.0520 (5)
O1	0.15719 (13)	0.17155 (13)	0.38424 (9)	0.0509 (4)
O2	0.07425 (14)	0.11701 (13)	0.50054 (9)	0.0467 (4)
O3	−0.02247 (15)	0.14867 (13)	0.27686 (9)	0.0522 (4)
O4	−0.1626 (2)	0.13838 (17)	0.51818 (12)	0.0779 (6)
O5	−0.10064 (18)	0.23912 (19)	0.60303 (10)	0.0743 (6)
S1	0.06292 (4)	0.15463 (4)	0.42754 (3)	0.03641 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0315 (10)	0.0356 (11)	0.0379 (10)	−0.0050 (9)	−0.0016 (8)	0.0003 (9)
C2	0.0348 (11)	0.0432 (12)	0.0383 (11)	−0.0042 (10)	0.0017 (9)	0.0074 (10)
C3	0.0457 (14)	0.0565 (15)	0.0558 (14)	0.0051 (12)	0.0116 (11)	0.0021 (12)
C4	0.0618 (17)	0.0420 (14)	0.0672 (16)	0.0094 (13)	0.0066 (13)	0.0048 (12)
C5	0.0707 (17)	0.0399 (13)	0.0559 (14)	−0.0009 (13)	0.0121 (13)	0.0125 (12)
C6	0.0521 (14)	0.0427 (13)	0.0427 (12)	−0.0032 (11)	0.0105 (10)	0.0024 (10)
C7	0.0424 (12)	0.0369 (11)	0.0328 (10)	0.0049 (10)	−0.0020 (9)	−0.0024 (9)
C8	0.0386 (11)	0.0380 (11)	0.0315 (10)	0.0037 (10)	−0.0018 (8)	−0.0051 (9)
C9	0.0399 (12)	0.0415 (12)	0.0331 (10)	0.0026 (10)	−0.0059 (9)	−0.0043 (9)
C10	0.0441 (12)	0.0414 (12)	0.0374 (11)	−0.0008 (10)	0.0012 (9)	−0.0078 (10)
C11	0.0454 (13)	0.0486 (13)	0.0492 (13)	−0.0030 (11)	−0.0073 (10)	−0.0171 (11)
C12	0.0526 (15)	0.0542 (15)	0.0457 (12)	0.0088 (12)	−0.0184 (11)	−0.0125 (12)
C13	0.0545 (14)	0.0402 (12)	0.0371 (11)	0.0100 (11)	−0.0077 (10)	−0.0051 (10)
C14	0.0701 (17)	0.0478 (14)	0.0577 (15)	−0.0141 (13)	−0.0055 (13)	−0.0004 (13)
N1	0.0475 (11)	0.0375 (10)	0.0337 (9)	−0.0093 (9)	−0.0039 (8)	0.0002 (8)
N2	0.0445 (12)	0.0611 (14)	0.0505 (12)	0.0044 (11)	0.0119 (9)	0.0157 (11)
O1	0.0370 (9)	0.0558 (10)	0.0600 (10)	−0.0012 (8)	0.0064 (8)	−0.0048 (8)
O2	0.0538 (10)	0.0472 (9)	0.0392 (8)	0.0012 (8)	−0.0141 (7)	0.0009 (7)
O3	0.0684 (11)	0.0454 (9)	0.0428 (9)	−0.0089 (9)	−0.0063 (8)	0.0099 (8)
O4	0.0936 (16)	0.0595 (13)	0.0806 (14)	−0.0224 (12)	0.0100 (12)	0.0177 (11)
O5	0.0813 (14)	0.0986 (17)	0.0429 (10)	0.0126 (13)	0.0139 (10)	0.0159 (11)
S1	0.0352 (3)	0.0378 (3)	0.0362 (3)	−0.0018 (2)	−0.0033 (2)	−0.0015 (2)

C1—C6	1.381 (3)	C9—H9	0.9300
C1—C2	1.389 (3)	C10—C11	1.386 (3)
C1—S1	1.772 (2)	C10—C14	1.489 (4)
C2—C3	1.369 (3)	C11—C12	1.384 (4)
C2—N2	1.478 (3)	C11—H11	0.9300
C3—C4	1.369 (4)	C12—C13	1.374 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.376 (4)	C13—H13	0.9300
C4—H4	0.9300	C14—H14A	0.9600
C5—C6	1.376 (3)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
C6—H6	0.9300	N1—S1	1.6374 (19)
C7—O3	1.205 (3)	N1—H1N	0.847 (16)
C7—N1	1.402 (3)	N2—O4	1.208 (3)
C7—C8	1.482 (3)	N2—O5	1.220 (3)
C8—C9	1.383 (3)	O1—S1	1.4159 (17)
C8—C13	1.389 (3)	O2—S1	1.4288 (16)
C9—C10	1.384 (3)
C6—C1—C2	118.2 (2)	C11—C10—C14	122.2 (2)
C6—C1—S1	118.96 (17)	C12—C11—C10	120.8 (2)
C2—C1—S1	122.75 (16)	C12—C11—H11	119.6
C3—C2—C1	121.6 (2)	C10—C11—H11	119.6
C3—C2—N2	116.8 (2)	C13—C12—C11	120.7 (2)
C1—C2—N2	121.6 (2)	C13—C12—H12	119.6
C4—C3—C2	119.3 (2)	C11—C12—H12	119.6
C4—C3—H3	120.3	C12—C13—C8	119.3 (2)
C2—C3—H3	120.3	C12—C13—H13	120.3
C3—C4—C5	120.3 (2)	C8—C13—H13	120.3
C3—C4—H4	119.9	C10—C14—H14A	109.5
C5—C4—H4	119.9	C10—C14—H14B	109.5
C4—C5—C6	120.3 (2)	H14A—C14—H14B	109.5
C4—C5—H5	119.9	C10—C14—H14C	109.5
C6—C5—H5	119.9	H14A—C14—H14C	109.5
C5—C6—C1	120.3 (2)	H14B—C14—H14C	109.5
C5—C6—H6	119.8	C7—N1—S1	123.95 (16)
C1—C6—H6	119.8	C7—N1—H1N	120.4 (17)
O3—C7—N1	120.8 (2)	S1—N1—H1N	113.5 (17)
O3—C7—C8	125.01 (19)	O4—N2—O5	125.7 (2)
N1—C7—C8	114.15 (19)	O4—N2—C2	117.4 (2)
C9—C8—C13	119.5 (2)	O5—N2—C2	116.9 (2)
C9—C8—C7	121.99 (18)	O1—S1—O2	119.82 (11)
C13—C8—C7	118.5 (2)	O1—S1—N1	109.29 (10)
C8—C9—C10	121.8 (2)	O2—S1—N1	104.51 (10)
C8—C9—H9	119.1	O1—S1—C1	107.53 (10)
C10—C9—H9	119.1	O2—S1—C1	108.46 (10)
C9—C10—C11	117.8 (2)	N1—S1—C1	106.52 (10)
C9—C10—C14	120.0 (2)
C6—C1—C2—C3	−1.2 (3)	C14—C10—C11—C12	−178.3 (2)
S1—C1—C2—C3	174.72 (19)	C10—C11—C12—C13	−1.7 (4)
C6—C1—C2—N2	178.5 (2)	C11—C12—C13—C8	−0.3 (4)
S1—C1—C2—N2	−5.6 (3)	C9—C8—C13—C12	2.0 (3)
C1—C2—C3—C4	2.0 (4)	C7—C8—C13—C12	−176.7 (2)
N2—C2—C3—C4	−177.7 (2)	O3—C7—N1—S1	−0.6 (3)
C2—C3—C4—C5	−1.4 (4)	C8—C7—N1—S1	−179.30 (15)
C3—C4—C5—C6	0.0 (4)	C3—C2—N2—O4	117.3 (3)
C4—C5—C6—C1	0.7 (4)	C1—C2—N2—O4	−62.4 (3)
C2—C1—C6—C5	−0.1 (3)	C3—C2—N2—O5	−61.8 (3)
S1—C1—C6—C5	−176.2 (2)	C1—C2—N2—O5	118.5 (3)
O3—C7—C8—C9	157.0 (2)	C7—N1—S1—O1	−51.6 (2)
N1—C7—C8—C9	−24.3 (3)	C7—N1—S1—O2	179.02 (18)
O3—C7—C8—C13	−24.3 (3)	C7—N1—S1—C1	64.3 (2)
N1—C7—C8—C13	154.3 (2)	C6—C1—S1—O1	16.5 (2)
C13—C8—C9—C10	−1.7 (3)	C2—C1—S1—O1	−159.39 (18)
C7—C8—C9—C10	176.87 (19)	C6—C1—S1—O2	147.47 (18)
C8—C9—C10—C11	−0.2 (3)	C2—C1—S1—O2	−28.4 (2)
C8—C9—C10—C14	180.0 (2)	C6—C1—S1—N1	−100.53 (19)
C9—C10—C11—C12	1.9 (3)	C2—C1—S1—N1	83.54 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.85 (2)	2.43 (2)	3.232 (3)	157 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.85 (2)	2.43 (2)	3.232 (3)	157 (2)

Symmetry code: (i) .