N-(4-Methyl-benzo-yl)-4-nitro-benzene-sulfonamide.

In the title compound, C(14)H(12)N(2)O(5)S, the dihedral angle between the nitro-phenyl group and the -S-NH-C-O fragment is 80.74 (17)° and that between the nitro-phenyl and methyl-phenyl groups is 87.66 (14)°. The C-S-N-C torsion angle at the S-N bond is -67.0 (3)°. In the crystal, mol-ecules are linked into C(4) chains via N-H⋯O hydrogen bonds.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-aryl­amides, see: Gowda et al. (1999 ▶, 2006 ▶). For N-aryl-methane­sulfonamides, see: Gowda et al. (2007 ▶). For N-(substituted-benzo­yl)-aryl­sulfonamides, see: Suchetan et al. (2010 ▶). For N-chloro­aryl­amides, see: Jyothi & Gowda (2004 ▶). For N-bromo­aryl­sulfonamides, see: Usha & Gowda (2006 ▶).

Experimental

Crystal data

C14H12N2O5S

M = 320.32

Orthorhombic,

a = 13.969 (1) Å

b = 9.6591 (6) Å

c = 21.026 (2) Å

V = 2837.0 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.40 × 0.18 × 0.18 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 = 0.956

7163 measured reflections

2864 independent reflections

1835 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.152

S = 1.16

2863 reflections

203 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.21 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/S1600536812007854/yk2044sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007854/yk2044Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007854/yk2044Isup3.cml

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

C14H12N2O5S	F(000) = 1328
Mr = 320.32	Dx = 1.500 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 818 reflections
a = 13.969 (1) Å	θ = 2.6–27.9°
b = 9.6591 (6) Å	µ = 0.25 mm−1
c = 21.026 (2) Å	T = 293 K
V = 2837.0 (4) Å3	Rod, colourless
Z = 8	0.40 × 0.18 × 0.18 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2864 independent reflections
Radiation source: fine-focus sealed tube	1836 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω and φ scans	θmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −7→17
Tmin = 0.905, Tmax = 0.956	k = −7→12
7163 measured reflections	l = −26→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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ2(Fo2) + (0.0409P)2 + 3.5546P] where P = (Fo2 + 2Fc2)/3
2863 reflections	(Δ/σ)max = 0.015
203 parameters	Δρmax = 0.32 e Å−3
7 restraints	Δρmin = −0.21 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.5261 (3)	0.2260 (4)	0.55537 (17)	0.0407 (9)
C2	0.4949 (3)	0.1161 (4)	0.5903 (2)	0.0490 (10)
H2	0.5302	0.0345	0.5911	0.059*
C3	0.4113 (3)	0.1260 (4)	0.6240 (2)	0.0533 (11)
H3	0.3899	0.0521	0.6486	0.064*
C4	0.3601 (3)	0.2459 (4)	0.62105 (19)	0.0450 (9)
C5	0.3893 (3)	0.3565 (5)	0.5862 (2)	0.0669 (13)
H5	0.3531	0.4372	0.5847	0.080*
C6	0.4737 (4)	0.3461 (5)	0.5534 (2)	0.0708 (14)
H6	0.4956	0.4209	0.5296	0.085*
C7	0.7385 (3)	0.3573 (4)	0.59457 (17)	0.0405 (9)
C8	0.8213 (3)	0.3558 (4)	0.63877 (17)	0.0385 (8)
C9	0.9003 (3)	0.2694 (4)	0.63104 (19)	0.0449 (9)
H9	0.9018	0.2066	0.5975	0.054*
C10	0.9763 (3)	0.2765 (4)	0.67281 (19)	0.0490 (10)
H10	1.0293	0.2199	0.6664	0.059*
C11	0.9750 (3)	0.3668 (4)	0.72441 (19)	0.0463 (10)
C12	0.8959 (3)	0.4520 (4)	0.73124 (19)	0.0497 (10)
H12	0.8938	0.5135	0.7652	0.060*
C13	0.8207 (3)	0.4481 (4)	0.68931 (18)	0.0458 (10)
H13	0.7691	0.5076	0.6948	0.055*
C14	1.0575 (3)	0.3736 (5)	0.7701 (2)	0.0638 (12)
H14A	1.1160	0.3865	0.7469	0.077*
H14B	1.0609	0.2889	0.7939	0.077*
H14C	1.0484	0.4499	0.7988	0.077*
N1	0.7201 (2)	0.2339 (3)	0.56360 (15)	0.0421 (8)
H1N	0.750 (3)	0.161 (3)	0.5748 (17)	0.051*
N2	0.2706 (3)	0.2572 (4)	0.65756 (17)	0.0569 (9)
O1	0.6446 (2)	0.0697 (3)	0.49280 (14)	0.0605 (8)
O2	0.6361 (2)	0.3183 (3)	0.46528 (13)	0.0647 (9)
O3	0.68781 (18)	0.4583 (3)	0.58609 (13)	0.0519 (7)
O4	0.2492 (3)	0.1639 (4)	0.6926 (2)	0.1066 (14)
O5	0.2239 (2)	0.3613 (4)	0.65262 (17)	0.0805 (10)
S1	0.63333 (7)	0.21032 (11)	0.51121 (5)	0.0474 (3)

	U11	U22	U33	U12	U13	U23
C1	0.042 (2)	0.042 (2)	0.038 (2)	−0.0042 (18)	−0.0084 (17)	0.0030 (17)
C2	0.046 (2)	0.035 (2)	0.067 (3)	0.0027 (18)	−0.002 (2)	0.005 (2)
C3	0.050 (2)	0.039 (2)	0.070 (3)	−0.003 (2)	0.003 (2)	0.012 (2)
C4	0.0384 (19)	0.044 (2)	0.053 (2)	−0.0040 (18)	−0.0034 (19)	0.0001 (18)
C5	0.061 (3)	0.052 (3)	0.088 (4)	0.018 (2)	0.014 (3)	0.024 (3)
C6	0.073 (3)	0.053 (3)	0.087 (3)	0.012 (2)	0.019 (3)	0.039 (3)
C7	0.041 (2)	0.0330 (19)	0.048 (2)	−0.0044 (17)	0.0068 (18)	−0.0038 (18)
C8	0.0351 (18)	0.0321 (18)	0.048 (2)	−0.0054 (16)	0.0051 (17)	−0.0010 (17)
C9	0.046 (2)	0.035 (2)	0.054 (2)	−0.0011 (18)	0.0016 (19)	−0.0090 (18)
C10	0.041 (2)	0.042 (2)	0.064 (3)	0.0021 (18)	0.002 (2)	−0.001 (2)
C11	0.043 (2)	0.049 (2)	0.047 (2)	−0.007 (2)	0.0037 (18)	0.001 (2)
C12	0.048 (2)	0.056 (2)	0.045 (2)	−0.007 (2)	0.0065 (19)	−0.013 (2)
C13	0.040 (2)	0.044 (2)	0.053 (2)	0.0000 (18)	0.0099 (19)	−0.0075 (19)
C14	0.055 (3)	0.085 (3)	0.052 (3)	−0.005 (2)	−0.007 (2)	−0.002 (2)
N1	0.0432 (18)	0.0345 (17)	0.0487 (19)	−0.0012 (14)	−0.0045 (15)	−0.0009 (15)
N2	0.051 (2)	0.056 (2)	0.064 (2)	−0.0004 (19)	0.0042 (19)	0.0004 (19)
O1	0.0604 (18)	0.0604 (18)	0.0606 (18)	−0.0056 (15)	0.0001 (15)	−0.0237 (15)
O2	0.069 (2)	0.081 (2)	0.0444 (16)	−0.0037 (17)	0.0040 (15)	0.0182 (16)
O3	0.0455 (16)	0.0353 (14)	0.0749 (19)	0.0039 (13)	−0.0010 (14)	−0.0027 (14)
O4	0.098 (3)	0.081 (2)	0.140 (3)	0.004 (2)	0.058 (2)	0.026 (2)
O5	0.062 (2)	0.086 (2)	0.094 (3)	0.0287 (19)	0.0031 (18)	0.004 (2)
S1	0.0490 (6)	0.0523 (6)	0.0409 (5)	−0.0053 (5)	−0.0008 (5)	−0.0027 (5)

C1—C2	1.362 (5)	C9—H9	0.9300
C1—C6	1.373 (5)	C10—C11	1.392 (5)
C1—S1	1.769 (4)	C10—H10	0.9300
C2—C3	1.369 (5)	C11—C12	1.385 (5)
C2—H2	0.9300	C11—C14	1.502 (5)
C3—C4	1.363 (5)	C12—C13	1.372 (5)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.359 (6)	C13—H13	0.9300
C4—N2	1.471 (5)	C14—H14A	0.9600
C5—C6	1.369 (6)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
C6—H6	0.9300	N1—S1	1.654 (3)
C7—O3	1.218 (4)	N1—H1N	0.852 (19)
C7—N1	1.383 (4)	N2—O4	1.202 (5)
C7—C8	1.484 (5)	N2—O5	1.203 (4)
C8—C13	1.387 (5)	O1—S1	1.421 (3)
C8—C9	1.393 (5)	O2—S1	1.422 (3)
C9—C10	1.380 (5)
C2—C1—C6	120.3 (4)	C11—C10—H10	119.4
C2—C1—S1	119.1 (3)	C12—C11—C10	117.6 (4)
C6—C1—S1	120.5 (3)	C12—C11—C14	121.3 (4)
C1—C2—C3	119.9 (4)	C10—C11—C14	121.1 (4)
C1—C2—H2	120.1	C13—C12—C11	121.9 (4)
C3—C2—H2	120.1	C13—C12—H12	119.1
C4—C3—C2	118.9 (4)	C11—C12—H12	119.1
C4—C3—H3	120.6	C12—C13—C8	120.4 (4)
C2—C3—H3	120.6	C12—C13—H13	119.8
C5—C4—C3	122.4 (4)	C8—C13—H13	119.8
C5—C4—N2	118.6 (4)	C11—C14—H14A	109.5
C3—C4—N2	119.0 (4)	C11—C14—H14B	109.5
C4—C5—C6	118.2 (4)	H14A—C14—H14B	109.5
C4—C5—H5	120.9	C11—C14—H14C	109.5
C6—C5—H5	120.9	H14A—C14—H14C	109.5
C5—C6—C1	120.4 (4)	H14B—C14—H14C	109.5
C5—C6—H6	119.8	C7—N1—S1	124.7 (3)
C1—C6—H6	119.8	C7—N1—H1N	119 (3)
O3—C7—N1	120.9 (3)	S1—N1—H1N	116 (3)
O3—C7—C8	123.5 (3)	O4—N2—O5	123.0 (4)
N1—C7—C8	115.6 (3)	O4—N2—C4	118.4 (4)
C13—C8—C9	118.6 (4)	O5—N2—C4	118.6 (4)
C13—C8—C7	118.0 (3)	O1—S1—O2	120.89 (19)
C9—C8—C7	123.4 (3)	O1—S1—N1	103.42 (17)
C10—C9—C8	120.4 (4)	O2—S1—N1	109.36 (17)
C10—C9—H9	119.8	O1—S1—C1	108.56 (18)
C8—C9—H9	119.8	O2—S1—C1	108.45 (18)
C9—C10—C11	121.2 (4)	N1—S1—C1	105.02 (16)
C9—C10—H10	119.4
C6—C1—C2—C3	−0.7 (6)	C14—C11—C12—C13	179.1 (4)
S1—C1—C2—C3	−179.1 (3)	C11—C12—C13—C8	1.0 (6)
C1—C2—C3—C4	1.1 (6)	C9—C8—C13—C12	−1.0 (5)
C2—C3—C4—C5	−0.6 (7)	C7—C8—C13—C12	−179.4 (3)
C2—C3—C4—N2	−179.6 (4)	O3—C7—N1—S1	2.5 (5)
C3—C4—C5—C6	−0.3 (7)	C8—C7—N1—S1	−178.8 (3)
N2—C4—C5—C6	178.7 (4)	C5—C4—N2—O4	−173.7 (5)
C4—C5—C6—C1	0.7 (8)	C3—C4—N2—O4	5.4 (6)
C2—C1—C6—C5	−0.2 (7)	C5—C4—N2—O5	3.9 (6)
S1—C1—C6—C5	178.2 (4)	C3—C4—N2—O5	−177.0 (4)
O3—C7—C8—C13	25.4 (5)	C7—N1—S1—O1	179.3 (3)
N1—C7—C8—C13	−153.2 (3)	C7—N1—S1—O2	49.2 (4)
O3—C7—C8—C9	−152.8 (4)	C7—N1—S1—C1	−67.0 (3)
N1—C7—C8—C9	28.5 (5)	C2—C1—S1—O1	29.9 (4)
C13—C8—C9—C10	−0.3 (6)	C6—C1—S1—O1	−148.6 (4)
C7—C8—C9—C10	177.9 (3)	C2—C1—S1—O2	162.9 (3)
C8—C9—C10—C11	1.8 (6)	C6—C1—S1—O2	−15.5 (4)
C9—C10—C11—C12	−1.8 (6)	C2—C1—S1—N1	−80.2 (3)
C9—C10—C11—C14	179.6 (4)	C6—C1—S1—N1	101.3 (4)
C10—C11—C12—C13	0.4 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.85 (2)	2.16 (2)	2.994 (4)	168 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.85 (2)	2.16 (2)	2.994 (4)	168 (4)

Symmetry code: (i) .