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

In title compound, C(14)H(12)N(2)O(5)S, the dihedral angle between the sulfonyl benzene ring and the -SO(2)-NH-C-O segment is 81.5 (2)° and that between the sulfonyl and the benzoyl benzene rings is 89.8 (1)°. In the crystal, mol-ecules are linked into chains along the b axis via inter-molecular N-H⋯O hydrogen bonds. C-H⋯O inter-actions are also observed.

Related literature

For background to our study of the effect of substituents on the structures of methane­sulfonamides, see: Gowda et al. (2007 ▶). For the effect of substituents on the structures of n class="Chemical">N-(ar­yl)-aryl­sulfonamides, see: Gowda et al. (2005 ▶). For the effect of substituents on the structures of N-(p-substituted benzo­yl)-p-substituted benzene­sulfonamides, see: Suchetan et al. (2010a ▶,b ▶).

Experimental

Crystal data

C14H12N2O5S

M = 320.32

Monoclinic,

a = 11.722 (3) Å

b = 5.137 (1) Å

c = 12.488 (3) Å

β = 105.09 (2)°

V = 726.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.40 × 0.12 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.907, T max = 0.980

2664 measured reflections

2265 independent reflections

1993 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.128

S = 1.17

2265 reflections

203 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.36 e Å−3

Absolute structure: Flack (1983 ▶), 605 Friedel pairs

Flack parameter: −0.05 (14)

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 datablocks I, global. DOI: 10.1107/S1600536811009470/vm2084sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009470/vm2084Isup2.hkl

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

C14H12N2O5S	F(000) = 332
Mr = 320.32	Dx = 1.465 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1463 reflections
a = 11.722 (3) Å	θ = 2.8–27.9°
b = 5.137 (1) Å	µ = 0.25 mm−1
c = 12.488 (3) Å	T = 293 K
β = 105.09 (2)°	Rod, colourless
V = 726.0 (3) Å3	0.40 × 0.12 × 0.08 mm
Z = 2

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2265 independent reflections
Radiation source: fine-focus sealed tube	1993 reflections with I > 2σ(I)
graphite	Rint = 0.030
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→14
Tmin = 0.907, Tmax = 0.980	k = −4→6
2664 measured reflections	l = −15→12

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)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.0525P)2 + 0.6019P] where P = (Fo2 + 2Fc2)/3
S = 1.17	(Δ/σ)max = 0.001
2265 reflections	Δρmax = 0.26 e Å−3
203 parameters	Δρmin = −0.36 e Å−3
2 restraints	Absolute structure: Flack (1983), 605 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.05 (14)

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	0.2737 (4)	0.1687 (9)	0.1307 (3)	0.0362 (9)
C2	0.2176 (4)	0.3782 (10)	0.0686 (4)	0.0460 (11)
H2	0.2510	0.4608	0.0178	0.055*
C3	0.1097 (4)	0.4617 (11)	0.0842 (4)	0.0532 (13)
H3	0.0708	0.6011	0.0428	0.064*
C4	0.0597 (4)	0.3414 (10)	0.1600 (4)	0.0481 (12)
C5	0.1184 (4)	0.1350 (11)	0.2208 (4)	0.0522 (13)
H5	0.0853	0.0517	0.2716	0.063*
C6	0.2260 (4)	0.0498 (12)	0.2073 (3)	0.0438 (9)
H6	0.2655	−0.0871	0.2500	0.053*
C7	0.5340 (4)	0.3078 (9)	0.2885 (3)	0.0371 (10)
C8	0.6231 (3)	0.5138 (8)	0.3373 (3)	0.0343 (10)
C9	0.6277 (4)	0.5947 (12)	0.4452 (3)	0.0509 (12)
H9	0.5779	0.5190	0.4834	0.061*
C10	0.7056 (5)	0.7857 (11)	0.4949 (4)	0.0549 (14)
H10	0.7075	0.8438	0.5658	0.066*
C11	0.7808 (4)	0.8898 (10)	0.4380 (4)	0.0449 (11)
C12	0.7788 (4)	0.8124 (10)	0.3324 (4)	0.0499 (12)
H12	0.8301	0.8864	0.2953	0.060*
C13	0.6993 (4)	0.6224 (10)	0.2822 (3)	0.0469 (13)
H13	0.6972	0.5672	0.2108	0.056*
C14	−0.0577 (4)	0.4337 (15)	0.1747 (5)	0.0717 (17)
H14A	−0.1132	0.2924	0.1602	0.086*
H14B	−0.0869	0.5734	0.1238	0.086*
H14C	−0.0476	0.4941	0.2493	0.086*
N1	0.5123 (3)	0.2647 (7)	0.1742 (3)	0.0329 (8)
H1N	0.525 (4)	0.377 (8)	0.129 (3)	0.039*
N2	0.8665 (4)	1.0941 (10)	0.4911 (3)	0.0568 (11)
O1	0.4318 (3)	−0.1903 (6)	0.1572 (3)	0.0502 (8)
O2	0.4040 (3)	0.0951 (7)	−0.0061 (2)	0.0487 (8)
O3	0.4829 (3)	0.1812 (7)	0.3440 (2)	0.0542 (9)
O4	0.9267 (4)	1.1940 (9)	0.4363 (4)	0.0806 (13)
O5	0.8702 (4)	1.1530 (10)	0.5865 (3)	0.0890 (15)
S1	0.40811 (9)	0.0583 (2)	0.10898 (7)	0.0359 (3)

	U11	U22	U33	U12	U13	U23
C1	0.040 (2)	0.035 (2)	0.0326 (19)	0.0028 (19)	0.0070 (16)	−0.0031 (18)
C2	0.048 (3)	0.039 (3)	0.050 (3)	−0.002 (2)	0.013 (2)	0.001 (2)
C3	0.052 (3)	0.053 (3)	0.049 (3)	0.015 (2)	0.003 (2)	0.010 (2)
C4	0.041 (2)	0.061 (3)	0.038 (2)	0.003 (2)	0.0028 (19)	−0.006 (2)
C5	0.047 (2)	0.065 (4)	0.046 (2)	−0.002 (2)	0.0154 (19)	0.003 (2)
C6	0.048 (2)	0.045 (2)	0.0384 (19)	0.003 (3)	0.0112 (17)	0.005 (3)
C7	0.038 (2)	0.044 (3)	0.031 (2)	0.006 (2)	0.0105 (17)	0.0044 (19)
C8	0.0359 (19)	0.039 (3)	0.0254 (16)	0.0066 (19)	0.0035 (14)	−0.0010 (17)
C9	0.058 (3)	0.063 (4)	0.0313 (19)	−0.005 (3)	0.0122 (18)	0.000 (2)
C10	0.073 (3)	0.058 (4)	0.031 (2)	0.001 (3)	0.009 (2)	−0.007 (2)
C11	0.047 (2)	0.038 (3)	0.043 (2)	0.008 (2)	−0.001 (2)	0.002 (2)
C12	0.051 (3)	0.057 (3)	0.044 (2)	−0.011 (2)	0.015 (2)	−0.008 (2)
C13	0.047 (2)	0.063 (4)	0.0330 (19)	−0.005 (2)	0.0133 (18)	−0.008 (2)
C14	0.049 (3)	0.099 (5)	0.066 (3)	0.018 (3)	0.013 (3)	−0.001 (3)
N1	0.0442 (19)	0.030 (2)	0.0241 (16)	0.0003 (16)	0.0081 (14)	0.0031 (13)
N2	0.064 (2)	0.047 (3)	0.048 (2)	0.002 (2)	−0.0050 (18)	−0.005 (2)
O1	0.053 (2)	0.037 (2)	0.061 (2)	0.0047 (16)	0.0156 (15)	−0.0032 (15)
O2	0.0562 (17)	0.060 (2)	0.0305 (13)	−0.0034 (18)	0.0115 (12)	−0.0111 (16)
O3	0.062 (2)	0.069 (2)	0.0339 (15)	−0.0161 (19)	0.0162 (14)	0.0028 (16)
O4	0.080 (3)	0.077 (3)	0.074 (3)	−0.031 (3)	0.002 (2)	−0.004 (2)
O5	0.113 (3)	0.089 (4)	0.056 (2)	−0.019 (3)	0.006 (2)	−0.029 (2)
S1	0.0428 (5)	0.0325 (5)	0.0324 (4)	0.0018 (6)	0.0099 (4)	−0.0027 (5)

C1—C6	1.371 (6)	C9—H9	0.9300
C1—C2	1.388 (6)	C10—C11	1.376 (7)
C1—S1	1.761 (4)	C10—H10	0.9300
C2—C3	1.396 (6)	C11—C12	1.372 (6)
C2—H2	0.9300	C11—N2	1.485 (6)
C3—C4	1.383 (7)	C12—C13	1.382 (6)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.379 (7)	C13—H13	0.9300
C4—C14	1.511 (7)	C14—H14A	0.9600
C5—C6	1.385 (6)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
C6—H6	0.9300	N1—S1	1.661 (4)
C7—O3	1.215 (5)	N1—H1N	0.85 (3)
C7—N1	1.401 (5)	N2—O4	1.217 (6)
C7—C8	1.500 (6)	N2—O5	1.219 (5)
C8—C13	1.379 (6)	O1—S1	1.409 (3)
C8—C9	1.398 (5)	O2—S1	1.438 (3)
C9—C10	1.374 (7)
C6—C1—C2	121.0 (4)	C11—C10—H10	120.5
C6—C1—S1	120.5 (4)	C12—C11—C10	122.1 (5)
C2—C1—S1	118.4 (3)	C12—C11—N2	118.3 (4)
C1—C2—C3	118.3 (4)	C10—C11—N2	119.6 (4)
C1—C2—H2	120.8	C11—C12—C13	118.7 (4)
C3—C2—H2	120.8	C11—C12—H12	120.6
C4—C3—C2	121.3 (5)	C13—C12—H12	120.6
C4—C3—H3	119.4	C8—C13—C12	120.5 (4)
C2—C3—H3	119.4	C8—C13—H13	119.7
C5—C4—C3	118.7 (4)	C12—C13—H13	119.7
C5—C4—C14	121.0 (5)	C4—C14—H14A	109.5
C3—C4—C14	120.3 (5)	C4—C14—H14B	109.5
C4—C5—C6	121.1 (4)	H14A—C14—H14B	109.5
C4—C5—H5	119.5	C4—C14—H14C	109.5
C6—C5—H5	119.5	H14A—C14—H14C	109.5
C1—C6—C5	119.5 (5)	H14B—C14—H14C	109.5
C1—C6—H6	120.2	C7—N1—S1	121.0 (3)
C5—C6—H6	120.2	C7—N1—H1N	124 (3)
O3—C7—N1	120.7 (4)	S1—N1—H1N	110 (3)
O3—C7—C8	122.7 (4)	O4—N2—O5	124.5 (5)
N1—C7—C8	116.6 (3)	O4—N2—C11	118.1 (4)
C13—C8—C9	119.5 (4)	O5—N2—C11	117.4 (5)
C13—C8—C7	123.8 (3)	O1—S1—O2	119.9 (2)
C9—C8—C7	116.7 (4)	O1—S1—N1	109.32 (19)
C10—C9—C8	120.1 (4)	O2—S1—N1	103.62 (18)
C10—C9—H9	119.9	O1—S1—C1	108.1 (2)
C8—C9—H9	119.9	O2—S1—C1	108.24 (19)
C9—C10—C11	119.0 (4)	N1—S1—C1	106.99 (19)
C9—C10—H10	120.5
C6—C1—C2—C3	−1.4 (7)	N2—C11—C12—C13	−180.0 (4)
S1—C1—C2—C3	178.6 (4)	C9—C8—C13—C12	−0.9 (7)
C1—C2—C3—C4	0.5 (7)	C7—C8—C13—C12	179.7 (4)
C2—C3—C4—C5	0.0 (7)	C11—C12—C13—C8	0.3 (7)
C2—C3—C4—C14	−179.4 (5)	O3—C7—N1—S1	5.4 (5)
C3—C4—C5—C6	0.5 (7)	C8—C7—N1—S1	−175.2 (3)
C14—C4—C5—C6	179.9 (5)	C12—C11—N2—O4	4.0 (7)
C2—C1—C6—C5	1.9 (7)	C10—C11—N2—O4	−175.5 (5)
S1—C1—C6—C5	−178.1 (4)	C12—C11—N2—O5	−177.1 (5)
C4—C5—C6—C1	−1.4 (7)	C10—C11—N2—O5	3.4 (7)
O3—C7—C8—C13	166.2 (4)	C7—N1—S1—O1	−58.2 (4)
N1—C7—C8—C13	−13.2 (6)	C7—N1—S1—O2	172.9 (3)
O3—C7—C8—C9	−13.2 (6)	C7—N1—S1—C1	58.7 (3)
N1—C7—C8—C9	167.4 (4)	C6—C1—S1—O1	15.4 (4)
C13—C8—C9—C10	1.7 (7)	C2—C1—S1—O1	−164.7 (3)
C7—C8—C9—C10	−178.9 (4)	C6—C1—S1—O2	146.7 (4)
C8—C9—C10—C11	−1.9 (8)	C2—C1—S1—O2	−33.4 (4)
C9—C10—C11—C12	1.3 (8)	C6—C1—S1—N1	−102.2 (4)
C9—C10—C11—N2	−179.3 (4)	C2—C1—S1—N1	77.7 (4)
C10—C11—C12—C13	−0.5 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.85 (3)	2.22 (3)	3.054 (4)	164 (4)
N1—H1N···O1ii	0.85 (3)	2.54 (4)	2.944 (5)	110 (3)
C9—H9···O3iii	0.93	2.58	3.254 (5)	130
C13—H13···O2i	0.93	2.53	3.347 (5)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.85 (3)	2.22 (3)	3.054 (4)	164 (4)
N1—H1N⋯O1ii	0.85 (3)	2.54 (4)	2.944 (5)	110 (3)
C9—H9⋯O3iii	0.93	2.58	3.254 (5)	130
C13—H13⋯O2i	0.93	2.53	3.347 (5)	147

Symmetry codes: (i) ; (ii) ; (iii) .