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

In the title compound, C(13)H(12)N(2)O(4)S, the dihedral angle between the benzene rings is 73.64 (7)°. The amide H atom exhibits bifurcated hydrogen bonding: an intra-molecular N-H⋯O hydrogen bond generates an S(7) motif while in the crystal, N-H⋯O(S) hydrogen bonds link the mol-ecules into zigzag C(4) chains running along the b axis.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Alkan et al. (2011 ▶); Bowes et al. (2003 ▶); Gowda et al. (2000 ▶); Saeed et al. (2010 ▶); Shahwar et al. (2012 ▶) of N-aryl­sulfonamides, see: Chaithanya et al. (2012 ▶); Gowda et al. (2002 ▶) and of N-chloro­aryl­sulfonamides, see: Gowda & Shetty (2004 ▶); Shetty & Gowda (2004 ▶). For hydrogen-bonding patterns and motifs, see: Adsmond et al. (2001 ▶); Allen et al. (1998 ▶); Bernstein et al. (1995 ▶); Etter (1990 ▶).

Experimental

Crystal data

C13H12N2O4S

M = 292.31

Monoclinic,

a = 9.0292 (6) Å

b = 9.6498 (7) Å

c = 15.878 (1) Å

β = 103.763 (8)°

V = 1343.73 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 293 K

0.40 × 0.28 × 0.28 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.905, T max = 0.932

4756 measured reflections

2750 independent reflections

2316 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.108

S = 1.06

2750 reflections

185 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.38 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/S1600536812034009/bt5988sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034009/bt5988Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034009/bt5988Isup3.cml

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

C13H12N2O4S	F(000) = 608
Mr = 292.31	Dx = 1.445 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2679 reflections
a = 9.0292 (6) Å	θ = 2.6–27.7°
b = 9.6498 (7) Å	µ = 0.26 mm−1
c = 15.878 (1) Å	T = 293 K
β = 103.763 (8)°	Prism, brown
V = 1343.73 (16) Å3	0.40 × 0.28 × 0.28 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2750 independent reflections
Radiation source: fine-focus sealed tube	2316 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.011
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −11→7
Tmin = 0.905, Tmax = 0.932	k = −12→8
4756 measured reflections	l = −15→19

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0514P)2 + 0.5996P] where P = (Fo2 + 2Fc2)/3
2750 reflections	(Δ/σ)max = 0.001
185 parameters	Δρmax = 0.30 e Å−3
1 restraint	Δρmin = −0.38 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
C1	0.3713 (2)	0.13280 (19)	0.58299 (11)	0.0375 (4)
C2	0.4187 (2)	0.18945 (19)	0.51278 (12)	0.0401 (4)
C3	0.3604 (2)	0.1431 (2)	0.42923 (13)	0.0524 (5)
H3	0.3953	0.1805	0.3835	0.063*
C4	0.2502 (3)	0.0412 (2)	0.41374 (15)	0.0581 (6)
H4	0.2099	0.0105	0.3574	0.070*
C5	0.1998 (3)	−0.0150 (2)	0.48125 (15)	0.0562 (5)
H5	0.1243	−0.0826	0.4706	0.067*
C6	0.2620 (2)	0.0294 (2)	0.56580 (14)	0.0481 (5)
H6	0.2295	−0.0111	0.6114	0.058*
C7	0.22779 (19)	0.35535 (19)	0.69038 (11)	0.0365 (4)
C8	0.1874 (2)	0.4794 (2)	0.64721 (12)	0.0425 (4)
H8	0.2624	0.5337	0.6323	0.051*
C9	0.0373 (2)	0.5240 (3)	0.62577 (14)	0.0570 (6)
C10	−0.0715 (2)	0.4398 (3)	0.64794 (18)	0.0735 (8)
H10	−0.1730	0.4678	0.6344	0.088*
C11	−0.0324 (3)	0.3147 (3)	0.68975 (19)	0.0726 (8)
H11	−0.1080	0.2593	0.7030	0.087*
C12	0.1188 (2)	0.2707 (2)	0.71234 (14)	0.0526 (5)
H12	0.1458	0.1872	0.7412	0.063*
C13	−0.0030 (4)	0.6597 (3)	0.5786 (2)	0.0886 (10)
H13A	0.0591	0.6723	0.5378	0.133*
H13B	0.0148	0.7345	0.6197	0.133*
H13C	−0.1086	0.6588	0.5483	0.133*
N1	0.38724 (17)	0.32157 (16)	0.71545 (10)	0.0381 (3)
H1N	0.444 (2)	0.3866 (19)	0.7069 (13)	0.046*
N2	0.53010 (19)	0.30367 (18)	0.52293 (11)	0.0471 (4)
O1	0.39747 (18)	0.06967 (15)	0.74298 (9)	0.0562 (4)
O2	0.61404 (15)	0.18892 (17)	0.70619 (9)	0.0558 (4)
O3	0.52327 (18)	0.39619 (17)	0.57411 (10)	0.0595 (4)
O4	0.6207 (2)	0.30177 (19)	0.47697 (13)	0.0743 (5)
S1	0.45362 (5)	0.17305 (5)	0.69406 (3)	0.04018 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0392 (9)	0.0359 (9)	0.0394 (9)	0.0107 (7)	0.0134 (7)	0.0037 (7)
C2	0.0391 (9)	0.0423 (10)	0.0417 (9)	0.0137 (8)	0.0148 (7)	0.0070 (8)
C3	0.0578 (12)	0.0615 (13)	0.0408 (10)	0.0197 (10)	0.0174 (9)	0.0054 (9)
C4	0.0625 (13)	0.0605 (13)	0.0479 (12)	0.0183 (11)	0.0064 (10)	−0.0108 (10)
C5	0.0533 (12)	0.0471 (12)	0.0662 (14)	0.0030 (10)	0.0103 (10)	−0.0119 (10)
C6	0.0506 (11)	0.0412 (10)	0.0568 (12)	0.0038 (9)	0.0210 (9)	0.0012 (9)
C7	0.0335 (9)	0.0429 (10)	0.0351 (9)	−0.0014 (7)	0.0122 (7)	−0.0093 (7)
C8	0.0410 (10)	0.0463 (10)	0.0412 (10)	0.0033 (8)	0.0118 (8)	−0.0075 (8)
C9	0.0468 (11)	0.0674 (14)	0.0543 (12)	0.0179 (10)	0.0068 (9)	−0.0180 (11)
C10	0.0357 (11)	0.092 (2)	0.0902 (19)	0.0104 (12)	0.0092 (11)	−0.0365 (16)
C11	0.0441 (12)	0.0830 (19)	0.100 (2)	−0.0230 (12)	0.0362 (13)	−0.0365 (16)
C12	0.0487 (11)	0.0513 (12)	0.0646 (13)	−0.0104 (9)	0.0271 (10)	−0.0111 (10)
C13	0.091 (2)	0.089 (2)	0.0801 (18)	0.0511 (17)	0.0098 (15)	−0.0004 (15)
N1	0.0341 (8)	0.0415 (8)	0.0400 (8)	−0.0020 (6)	0.0114 (6)	−0.0005 (7)
N2	0.0455 (9)	0.0512 (10)	0.0494 (9)	0.0109 (7)	0.0208 (7)	0.0171 (8)
O1	0.0734 (10)	0.0498 (8)	0.0495 (8)	0.0103 (7)	0.0229 (7)	0.0204 (7)
O2	0.0380 (7)	0.0738 (10)	0.0532 (8)	0.0161 (7)	0.0063 (6)	0.0103 (7)
O3	0.0679 (10)	0.0580 (9)	0.0585 (9)	−0.0082 (8)	0.0270 (8)	0.0015 (8)
O4	0.0710 (11)	0.0763 (12)	0.0945 (13)	0.0046 (9)	0.0569 (10)	0.0142 (10)
S1	0.0418 (3)	0.0434 (3)	0.0359 (2)	0.00993 (19)	0.01056 (18)	0.00990 (18)

C1—C6	1.384 (3)	C9—C10	1.384 (4)
C1—C2	1.397 (2)	C9—C13	1.510 (4)
C1—S1	1.7861 (19)	C10—C11	1.382 (4)
C2—C3	1.380 (3)	C10—H10	0.9300
C2—N2	1.475 (3)	C11—C12	1.393 (3)
C3—C4	1.380 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.371 (3)	C13—H13A	0.9600
C4—H4	0.9300	C13—H13B	0.9600
C5—C6	1.394 (3)	C13—H13C	0.9600
C5—H5	0.9300	N1—S1	1.6203 (16)
C6—H6	0.9300	N1—H1N	0.839 (15)
C7—C8	1.384 (3)	N2—O3	1.219 (2)
C7—C12	1.386 (3)	N2—O4	1.219 (2)
C7—N1	1.437 (2)	O1—S1	1.4293 (14)
C8—C9	1.385 (3)	O2—S1	1.4234 (14)
C8—H8	0.9300
C6—C1—C2	117.66 (18)	C11—C10—C9	121.2 (2)
C6—C1—S1	117.47 (14)	C11—C10—H10	119.4
C2—C1—S1	124.62 (15)	C9—C10—H10	119.4
C3—C2—C1	121.41 (19)	C10—C11—C12	120.9 (2)
C3—C2—N2	116.18 (17)	C10—C11—H11	119.5
C1—C2—N2	122.40 (17)	C12—C11—H11	119.5
C4—C3—C2	119.8 (2)	C7—C12—C11	117.8 (2)
C4—C3—H3	120.1	C7—C12—H12	121.1
C2—C3—H3	120.1	C11—C12—H12	121.1
C5—C4—C3	120.1 (2)	C9—C13—H13A	109.5
C5—C4—H4	119.9	C9—C13—H13B	109.5
C3—C4—H4	119.9	H13A—C13—H13B	109.5
C4—C5—C6	120.0 (2)	C9—C13—H13C	109.5
C4—C5—H5	120.0	H13A—C13—H13C	109.5
C6—C5—H5	120.0	H13B—C13—H13C	109.5
C1—C6—C5	121.08 (19)	C7—N1—S1	122.60 (12)
C1—C6—H6	119.5	C7—N1—H1N	113.2 (14)
C5—C6—H6	119.5	S1—N1—H1N	111.0 (14)
C8—C7—C12	121.04 (18)	O3—N2—O4	123.90 (19)
C8—C7—N1	117.49 (16)	O3—N2—C2	118.62 (15)
C12—C7—N1	121.39 (18)	O4—N2—C2	117.44 (18)
C7—C8—C9	121.1 (2)	O2—S1—O1	118.86 (9)
C7—C8—H8	119.4	O2—S1—N1	106.96 (9)
C9—C8—H8	119.4	O1—S1—N1	107.87 (8)
C10—C9—C8	117.9 (2)	O2—S1—C1	109.16 (9)
C10—C9—C13	122.2 (2)	O1—S1—C1	105.46 (9)
C8—C9—C13	119.9 (2)	N1—S1—C1	108.15 (8)
C6—C1—C2—C3	−0.8 (3)	C8—C7—C12—C11	−0.2 (3)
S1—C1—C2—C3	173.28 (14)	N1—C7—C12—C11	176.49 (18)
C6—C1—C2—N2	177.64 (16)	C10—C11—C12—C7	−0.9 (3)
S1—C1—C2—N2	−8.3 (2)	C8—C7—N1—S1	−129.88 (15)
C1—C2—C3—C4	1.6 (3)	C12—C7—N1—S1	53.3 (2)
N2—C2—C3—C4	−176.88 (17)	C3—C2—N2—O3	139.47 (18)
C2—C3—C4—C5	−0.7 (3)	C1—C2—N2—O3	−39.0 (2)
C3—C4—C5—C6	−1.1 (3)	C3—C2—N2—O4	−38.1 (2)
C2—C1—C6—C5	−1.0 (3)	C1—C2—N2—O4	143.39 (19)
S1—C1—C6—C5	−175.49 (15)	C7—N1—S1—O2	164.42 (14)
C4—C5—C6—C1	1.9 (3)	C7—N1—S1—O1	−66.64 (16)
C12—C7—C8—C9	1.0 (3)	C7—N1—S1—C1	46.97 (16)
N1—C7—C8—C9	−175.76 (16)	C6—C1—S1—O2	136.48 (15)
C7—C8—C9—C10	−0.8 (3)	C2—C1—S1—O2	−37.61 (17)
C7—C8—C9—C13	−180.0 (2)	C6—C1—S1—O1	7.70 (16)
C8—C9—C10—C11	−0.3 (3)	C2—C1—S1—O1	−166.39 (15)
C13—C9—C10—C11	178.9 (2)	C6—C1—S1—N1	−107.49 (15)
C9—C10—C11—C12	1.2 (4)	C2—C1—S1—N1	78.42 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.84 (2)	2.30 (2)	3.055 (2)	151 (2)
N1—H1N···O3	0.84 (2)	2.39 (2)	2.894 (2)	120 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.84 (2)	2.30 (2)	3.055 (2)	151 (2)
N1—H1N⋯O3	0.84 (2)	2.39 (2)	2.894 (2)	120 (2)

Symmetry code: (i) .