N-(2-Methyl-phen-yl)-4-nitro-benzene-sulfonamide.

In the title compound, C(13)H(12)N(2)O(4)S, the dihedral angle between the planes of the rings is 51.11 (10)°. In the crystal, mol-ecules are linked into inversion dimers through pairs of N-H⋯O(S) hydrogen bonds.

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 & Weiss (1994 ▶); Saeed et al. (2010 ▶); Shahwar et al. (2012 ▶), of N-aryl­sulfonamides, see: Chaithanya et al. (2012 ▶); Gowda et al. (2005 ▶) and of N-chloro­aryl­sulfonamides, see: Gowda & Shetty (2004 ▶); Shetty & Gowda (2004 ▶).

Experimental

Crystal data

C13H12N2O4S

M = 292.31

Monoclinic,

a = 14.106 (1) Å

b = 7.0082 (5) Å

c = 14.854 (2) Å

β = 110.84 (1)°

V = 1372.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.44 × 0.44 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.898, T max = 0.942

4889 measured reflections

2781 independent reflections

2198 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.119

S = 1.08

2781 reflections

185 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.33 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/S1600536812036331/bt6824sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036331/bt6824Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812036331/bt6824Isup3.cml

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

C13H12N2O4S	F(000) = 608
Mr = 292.31	Dx = 1.415 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2269 reflections
a = 14.106 (1) Å	θ = 2.6–27.7°
b = 7.0082 (5) Å	µ = 0.25 mm−1
c = 14.854 (2) Å	T = 293 K
β = 110.84 (1)°	Prism, light brown
V = 1372.4 (2) Å3	0.44 × 0.44 × 0.24 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2781 independent reflections
Radiation source: fine-focus sealed tube	2198 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −16→17
Tmin = 0.898, Tmax = 0.942	k = −8→8
4889 measured reflections	l = −11→18

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0444P)2 + 0.7236P] where P = (Fo2 + 2Fc2)/3
2781 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.19 e Å−3
1 restraint	Δρmin = −0.33 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
S1	0.16315 (4)	0.55405 (8)	0.49925 (4)	0.05191 (19)
O1	0.22495 (12)	0.6861 (2)	0.47241 (13)	0.0623 (4)
O2	0.11524 (13)	0.6116 (2)	0.56500 (13)	0.0680 (5)
O3	0.3815 (2)	−0.2517 (4)	0.69841 (19)	0.1191 (9)
O4	0.45351 (17)	−0.2122 (3)	0.59408 (18)	0.0960 (7)
N1	0.07213 (13)	0.4839 (3)	0.40317 (15)	0.0539 (5)
H1N	0.0239 (16)	0.439 (3)	0.4158 (18)	0.065*
N2	0.3977 (2)	−0.1605 (4)	0.63546 (19)	0.0804 (7)
C1	0.23798 (16)	0.3504 (3)	0.54651 (16)	0.0493 (5)
C2	0.2147 (2)	0.2341 (4)	0.61097 (19)	0.0690 (7)
H2	0.1633	0.2678	0.6334	0.083*
C3	0.2686 (2)	0.0682 (4)	0.6414 (2)	0.0757 (8)
H3	0.2546	−0.0116	0.6852	0.091*
C4	0.34313 (18)	0.0224 (4)	0.60623 (17)	0.0613 (6)
C5	0.36773 (18)	0.1362 (4)	0.54339 (19)	0.0642 (6)
H5	0.4190	0.1012	0.5210	0.077*
C6	0.31531 (17)	0.3033 (4)	0.51386 (18)	0.0595 (6)
H6	0.3317	0.3845	0.4721	0.071*
C7	0.09202 (15)	0.3986 (3)	0.32411 (16)	0.0516 (5)
C8	0.06673 (17)	0.2084 (4)	0.30017 (18)	0.0605 (6)
C9	0.0841 (2)	0.1372 (5)	0.2200 (2)	0.0808 (9)
H9	0.0657	0.0121	0.2006	0.097*
C10	0.1274 (2)	0.2459 (7)	0.1691 (2)	0.0949 (11)
H10	0.1386	0.1938	0.1162	0.114*
C11	0.1544 (2)	0.4303 (6)	0.1948 (2)	0.0906 (11)
H11	0.1854	0.5027	0.1606	0.109*
C12	0.13538 (18)	0.5092 (5)	0.27233 (19)	0.0704 (7)
H12	0.1518	0.6360	0.2893	0.084*
C13	0.0228 (3)	0.0823 (4)	0.3571 (2)	0.0861 (9)
H13A	−0.0455	0.1215	0.3468	0.129*
H13B	0.0631	0.0923	0.4243	0.129*
H13C	0.0227	−0.0476	0.3365	0.129*

	U11	U22	U33	U12	U13	U23
S1	0.0489 (3)	0.0462 (3)	0.0676 (4)	−0.0081 (2)	0.0293 (3)	−0.0158 (3)
O1	0.0589 (9)	0.0503 (9)	0.0836 (12)	−0.0129 (7)	0.0325 (9)	−0.0083 (8)
O2	0.0634 (10)	0.0686 (11)	0.0845 (12)	−0.0109 (8)	0.0416 (9)	−0.0321 (9)
O3	0.140 (2)	0.1042 (19)	0.0991 (18)	0.0273 (16)	0.0256 (16)	0.0432 (15)
O4	0.0757 (13)	0.0803 (14)	0.1144 (18)	0.0190 (11)	0.0122 (13)	−0.0008 (13)
N1	0.0436 (10)	0.0542 (11)	0.0688 (12)	−0.0043 (8)	0.0263 (9)	−0.0118 (9)
N2	0.0741 (15)	0.0728 (16)	0.0712 (16)	0.0040 (13)	−0.0026 (13)	0.0051 (13)
C1	0.0481 (11)	0.0503 (12)	0.0524 (12)	−0.0083 (10)	0.0216 (10)	−0.0114 (10)
C2	0.0742 (16)	0.0780 (18)	0.0681 (16)	−0.0030 (14)	0.0418 (14)	−0.0009 (14)
C3	0.0884 (19)	0.0779 (19)	0.0641 (16)	−0.0036 (16)	0.0313 (15)	0.0141 (14)
C4	0.0569 (13)	0.0594 (14)	0.0550 (13)	−0.0014 (11)	0.0044 (11)	−0.0034 (11)
C5	0.0534 (13)	0.0703 (16)	0.0696 (16)	0.0039 (12)	0.0229 (12)	0.0001 (13)
C6	0.0533 (13)	0.0629 (14)	0.0695 (15)	−0.0008 (11)	0.0306 (12)	0.0032 (12)
C7	0.0370 (10)	0.0633 (14)	0.0532 (12)	0.0069 (10)	0.0142 (9)	−0.0045 (11)
C8	0.0497 (12)	0.0661 (15)	0.0635 (14)	0.0088 (11)	0.0174 (11)	−0.0150 (12)
C9	0.0664 (16)	0.097 (2)	0.0754 (18)	0.0128 (16)	0.0213 (15)	−0.0277 (17)
C10	0.0700 (18)	0.153 (4)	0.0624 (18)	0.019 (2)	0.0248 (15)	−0.021 (2)
C11	0.0658 (17)	0.149 (4)	0.0614 (17)	0.002 (2)	0.0279 (14)	0.012 (2)
C12	0.0561 (14)	0.0890 (19)	0.0644 (15)	0.0011 (13)	0.0193 (12)	0.0088 (14)
C13	0.108 (2)	0.0572 (16)	0.102 (2)	−0.0184 (16)	0.049 (2)	−0.0244 (16)

S1—O1	1.4221 (16)	C5—H5	0.9300
S1—O2	1.4292 (16)	C6—H6	0.9300
S1—N1	1.620 (2)	C7—C12	1.379 (3)
S1—C1	1.765 (2)	C7—C8	1.393 (3)
O3—N2	1.220 (3)	C8—C9	1.391 (3)
O4—N2	1.214 (3)	C8—C13	1.501 (4)
N1—C7	1.431 (3)	C9—C10	1.361 (5)
N1—H1N	0.830 (16)	C9—H9	0.9300
N2—C4	1.479 (3)	C10—C11	1.363 (5)
C1—C6	1.382 (3)	C10—H10	0.9300
C1—C2	1.383 (3)	C11—C12	1.387 (4)
C2—C3	1.375 (4)	C11—H11	0.9300
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.369 (4)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.363 (3)	C13—H13C	0.9600
C5—C6	1.371 (3)
O1—S1—O2	119.61 (10)	C5—C6—C1	119.7 (2)
O1—S1—N1	108.86 (11)	C5—C6—H6	120.2
O2—S1—N1	105.57 (10)	C1—C6—H6	120.2
O1—S1—C1	107.34 (10)	C12—C7—C8	121.3 (2)
O2—S1—C1	108.52 (11)	C12—C7—N1	118.6 (2)
N1—S1—C1	106.21 (10)	C8—C7—N1	120.1 (2)
C7—N1—S1	121.63 (14)	C9—C8—C7	117.0 (3)
C7—N1—H1N	116.3 (18)	C9—C8—C13	120.3 (3)
S1—N1—H1N	111.9 (18)	C7—C8—C13	122.6 (2)
O4—N2—O3	124.3 (3)	C10—C9—C8	121.7 (3)
O4—N2—C4	118.3 (3)	C10—C9—H9	119.2
O3—N2—C4	117.3 (3)	C8—C9—H9	119.2
C6—C1—C2	120.9 (2)	C9—C10—C11	120.7 (3)
C6—C1—S1	119.24 (18)	C9—C10—H10	119.6
C2—C1—S1	119.75 (18)	C11—C10—H10	119.6
C3—C2—C1	119.2 (2)	C10—C11—C12	119.5 (3)
C3—C2—H2	120.4	C10—C11—H11	120.2
C1—C2—H2	120.4	C12—C11—H11	120.2
C4—C3—C2	118.8 (2)	C7—C12—C11	119.6 (3)
C4—C3—H3	120.6	C7—C12—H12	120.2
C2—C3—H3	120.6	C11—C12—H12	120.2
C5—C4—C3	122.8 (2)	C8—C13—H13A	109.5
C5—C4—N2	118.4 (2)	C8—C13—H13B	109.5
C3—C4—N2	118.8 (3)	H13A—C13—H13B	109.5
C4—C5—C6	118.6 (2)	C8—C13—H13C	109.5
C4—C5—H5	120.7	H13A—C13—H13C	109.5
C6—C5—H5	120.7	H13B—C13—H13C	109.5
O1—S1—N1—C7	56.3 (2)	C3—C4—C5—C6	−0.3 (4)
O2—S1—N1—C7	−174.08 (18)	N2—C4—C5—C6	178.1 (2)
C1—S1—N1—C7	−59.0 (2)	C4—C5—C6—C1	−1.3 (4)
O1—S1—C1—C6	−29.1 (2)	C2—C1—C6—C5	2.0 (4)
O2—S1—C1—C6	−159.71 (18)	S1—C1—C6—C5	−174.02 (19)
N1—S1—C1—C6	87.2 (2)	S1—N1—C7—C12	−66.4 (3)
O1—S1—C1—C2	154.79 (19)	S1—N1—C7—C8	114.3 (2)
O2—S1—C1—C2	24.2 (2)	C12—C7—C8—C9	−2.1 (3)
N1—S1—C1—C2	−88.9 (2)	N1—C7—C8—C9	177.3 (2)
C6—C1—C2—C3	−1.0 (4)	C12—C7—C8—C13	177.8 (2)
S1—C1—C2—C3	175.0 (2)	N1—C7—C8—C13	−2.9 (3)
C1—C2—C3—C4	−0.6 (4)	C7—C8—C9—C10	2.4 (4)
C2—C3—C4—C5	1.2 (4)	C13—C8—C9—C10	−177.5 (3)
C2—C3—C4—N2	−177.1 (2)	C8—C9—C10—C11	−0.7 (5)
O4—N2—C4—C5	−8.4 (4)	C9—C10—C11—C12	−1.5 (5)
O3—N2—C4—C5	173.3 (3)	C8—C7—C12—C11	0.0 (4)
O4—N2—C4—C3	170.0 (3)	N1—C7—C12—C11	−179.4 (2)
O3—N2—C4—C3	−8.2 (4)	C10—C11—C12—C7	1.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.83 (2)	2.11 (2)	2.923 (2)	166 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.83 (2)	2.11 (2)	2.923 (2)	166 (2)

Symmetry code: (i) .