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

In the title compound, C(14)H(12)N(2)O(5)S, the conformation of the N-C bond in the C-SO(2)-NH-C(O) segment has gauche torsions with respect to the S=O bonds. The mol-ecule is twisted at the S atom, the C-S(O(2))-NH-C(O) torsion angle being 61.8 (5)°. The dihedral angle between the sulfonyl benzene ring and the -SO(2)-NH-C-O segment is 86.8 (2)° and that between the sulfonyl and the benzoyl benzene rings is 83.8 (2)°. In the crystal, mol-ecules are linked into zigzag chains along the a axis via N-H⋯O hydrogen bonds.

Related literature

For our study of the effect of substituents on the structures of N-(ar­yl)-amides, see: Gowda et al. (2000 ▶), on the structures of N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶) and on the structures of N-(p-substituted-benzo­yl)-p-substituted-benzene­sulfon­amides, see: Suchetan et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C14H12N2O5S

M = 320.32

Monoclinic,

a = 11.088 (2) Å

b = 5.3490 (7) Å

c = 12.344 (2) Å

β = 104.45 (2)°

V = 709.0 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 293 K

0.36 × 0.14 × 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 = 0.914, T max = 0.980

2485 measured reflections

1912 independent reflections

1701 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.146

S = 1.22

1912 reflections

203 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.49 e Å−3

Absolute structure: Flack (1983 ▶), 295 Friedel pairs

Flack parameter: 0.2 (2)

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/S1600536811009846/bq2287sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009846/bq2287Isup2.hkl

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

C14H12N2O5S	F(000) = 332
Mr = 320.32	Dx = 1.501 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1591 reflections
a = 11.088 (2) Å	θ = 2.9–28.0°
b = 5.3490 (7) Å	µ = 0.26 mm−1
c = 12.344 (2) Å	T = 293 K
β = 104.45 (2)°	Rod, colorless
V = 709.0 (2) Å3	0.36 × 0.14 × 0.08 mm
Z = 2

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1912 independent reflections
Radiation source: fine-focus sealed tube	1701 reflections with I > 2σ(I)
graphite	Rint = 0.031
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −11→13
Tmin = 0.914, Tmax = 0.980	k = −6→2
2485 measured reflections	l = −15→5

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)] = 0.058	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.146	w = 1/[σ2(Fo2) + (0.0445P)2 + 1.1687P] where P = (Fo2 + 2Fc2)/3
S = 1.22	(Δ/σ)max < 0.001
1912 reflections	Δρmax = 0.40 e Å−3
203 parameters	Δρmin = −0.49 e Å−3
2 restraints	Absolute structure: Flack (1983), 295 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.2 (2)

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	0.7626 (5)	0.1060 (12)	0.1331 (4)	0.0342 (12)
C2	0.6994 (5)	0.3107 (13)	0.0729 (5)	0.0423 (14)
C3	0.5918 (6)	0.3851 (16)	0.1032 (6)	0.0584 (19)
H3	0.5454	0.5171	0.0649	0.070*
C4	0.5522 (6)	0.2708 (18)	0.1870 (6)	0.064 (2)
H4	0.4819	0.3312	0.2066	0.076*
C5	0.6146 (6)	0.0673 (17)	0.2430 (6)	0.062 (2)
H5	0.5852	−0.0150	0.2977	0.075*
C6	0.7216 (5)	−0.0105 (17)	0.2157 (4)	0.0472 (14)
H6	0.7666	−0.1440	0.2540	0.057*
C7	1.0346 (5)	0.2574 (12)	0.2879 (4)	0.0366 (13)
C8	1.1292 (4)	0.4580 (11)	0.3348 (4)	0.0328 (14)
C9	1.1242 (5)	0.5551 (15)	0.4365 (4)	0.0476 (18)
H9	1.0667	0.4932	0.4732	0.057*
C10	1.2052 (6)	0.7466 (14)	0.4848 (5)	0.0488 (16)
H10	1.2013	0.8180	0.5526	0.059*
C11	1.2906 (5)	0.8261 (13)	0.4292 (5)	0.0409 (14)
C12	1.2986 (5)	0.7304 (14)	0.3293 (5)	0.0464 (16)
H12	1.3574	0.7902	0.2936	0.056*
C13	1.2161 (5)	0.5394 (15)	0.2817 (4)	0.0451 (17)
H13	1.2205	0.4681	0.2140	0.054*
C14	0.7364 (6)	0.4421 (13)	−0.0192 (5)	0.0554 (18)
H14A	0.7156	0.3408	−0.0855	0.067*
H14B	0.8245	0.4721	0.0015	0.067*
H14C	0.6929	0.5986	−0.0335	0.067*
N1	1.0112 (4)	0.2138 (9)	0.1743 (3)	0.0319 (10)
H1N	1.031 (5)	0.298 (11)	0.121 (4)	0.038*
N2	1.3751 (4)	1.0337 (13)	0.4783 (4)	0.0491 (13)
O1	0.9359 (4)	−0.2274 (9)	0.1691 (3)	0.0492 (11)
O2	0.9059 (3)	0.0189 (10)	−0.0029 (3)	0.0428 (9)
O3	0.9818 (4)	0.1447 (10)	0.3468 (3)	0.0539 (13)
O4	1.3758 (5)	1.0989 (12)	0.5732 (4)	0.0753 (16)
O5	1.4394 (4)	1.1259 (11)	0.4219 (4)	0.0690 (15)
S1	0.90691 (11)	0.0026 (3)	0.11283 (10)	0.0351 (3)

	U11	U22	U33	U12	U13	U23
C1	0.037 (3)	0.039 (3)	0.026 (2)	−0.002 (3)	0.0066 (19)	−0.006 (2)
C2	0.039 (3)	0.043 (4)	0.040 (3)	−0.004 (3)	0.000 (2)	−0.005 (3)
C3	0.037 (3)	0.062 (5)	0.068 (4)	0.008 (3)	−0.003 (3)	−0.009 (4)
C4	0.044 (3)	0.082 (6)	0.068 (5)	−0.008 (4)	0.021 (3)	−0.025 (5)
C5	0.051 (3)	0.081 (7)	0.059 (4)	−0.015 (4)	0.021 (3)	−0.003 (4)
C6	0.042 (3)	0.054 (4)	0.044 (3)	−0.006 (4)	0.007 (2)	−0.001 (4)
C7	0.031 (3)	0.041 (4)	0.036 (3)	0.001 (3)	0.005 (2)	0.005 (3)
C8	0.027 (2)	0.039 (4)	0.031 (2)	0.001 (2)	0.0022 (18)	0.005 (2)
C9	0.038 (3)	0.068 (6)	0.036 (3)	−0.006 (3)	0.008 (2)	−0.002 (3)
C10	0.050 (3)	0.053 (4)	0.041 (3)	0.001 (3)	0.007 (3)	−0.011 (3)
C11	0.031 (3)	0.044 (4)	0.041 (3)	0.004 (3)	−0.002 (2)	0.004 (3)
C12	0.035 (3)	0.061 (5)	0.043 (3)	−0.010 (3)	0.008 (2)	0.000 (3)
C13	0.038 (3)	0.065 (5)	0.031 (2)	−0.008 (3)	0.006 (2)	−0.005 (3)
C14	0.064 (4)	0.044 (5)	0.052 (3)	0.007 (3)	0.001 (3)	0.005 (3)
N1	0.036 (2)	0.032 (3)	0.026 (2)	−0.004 (2)	0.0047 (17)	0.0006 (19)
N2	0.036 (2)	0.046 (4)	0.057 (3)	0.003 (3)	−0.002 (2)	−0.006 (3)
O1	0.052 (2)	0.039 (3)	0.052 (2)	0.007 (2)	0.0060 (19)	0.006 (2)
O2	0.0432 (19)	0.047 (3)	0.0359 (17)	0.002 (2)	0.0052 (14)	−0.006 (2)
O3	0.054 (2)	0.066 (3)	0.040 (2)	−0.015 (2)	0.0095 (18)	0.003 (2)
O4	0.083 (4)	0.079 (4)	0.059 (3)	−0.020 (3)	0.010 (2)	−0.027 (3)
O5	0.053 (3)	0.070 (4)	0.083 (3)	−0.020 (3)	0.015 (2)	−0.002 (3)
S1	0.0365 (6)	0.0337 (7)	0.0330 (6)	0.0020 (7)	0.0043 (4)	−0.0006 (7)

C1—C6	1.366 (8)	C9—H9	0.9300
C1—C2	1.408 (9)	C10—C11	1.369 (9)
C1—S1	1.769 (5)	C10—H10	0.9300
C2—C3	1.395 (9)	C11—C12	1.359 (8)
C2—C14	1.479 (8)	C11—N2	1.481 (9)
C3—C4	1.365 (10)	C12—C13	1.399 (9)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.380 (12)	C13—H13	0.9300
C4—H4	0.9300	C14—H14A	0.9600
C5—C6	1.377 (8)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
C6—H6	0.9300	N1—S1	1.659 (5)
C7—O3	1.202 (6)	N1—H1N	0.87 (3)
C7—N1	1.381 (6)	N2—O5	1.219 (7)
C7—C8	1.511 (8)	N2—O4	1.220 (6)
C8—C13	1.366 (7)	O1—S1	1.410 (5)
C8—C9	1.371 (7)	O2—S1	1.428 (3)
C9—C10	1.395 (9)
C6—C1—C2	122.3 (5)	C9—C10—H10	121.1
C6—C1—S1	116.4 (5)	C12—C11—C10	123.3 (6)
C2—C1—S1	121.1 (4)	C12—C11—N2	118.4 (5)
C3—C2—C1	115.2 (6)	C10—C11—N2	118.3 (5)
C3—C2—C14	119.4 (6)	C11—C12—C13	118.2 (6)
C1—C2—C14	125.4 (5)	C11—C12—H12	120.9
C4—C3—C2	122.3 (7)	C13—C12—H12	120.9
C4—C3—H3	118.9	C8—C13—C12	119.8 (5)
C2—C3—H3	118.9	C8—C13—H13	120.1
C3—C4—C5	121.2 (7)	C12—C13—H13	120.1
C3—C4—H4	119.4	C2—C14—H14A	109.5
C5—C4—H4	119.4	C2—C14—H14B	109.5
C6—C5—C4	118.0 (7)	H14A—C14—H14B	109.5
C6—C5—H5	121.0	C2—C14—H14C	109.5
C4—C5—H5	121.0	H14A—C14—H14C	109.5
C1—C6—C5	120.9 (7)	H14B—C14—H14C	109.5
C1—C6—H6	119.6	C7—N1—S1	120.8 (4)
C5—C6—H6	119.6	C7—N1—H1N	132 (4)
O3—C7—N1	122.2 (5)	S1—N1—H1N	106 (4)
O3—C7—C8	121.4 (5)	O5—N2—O4	124.6 (6)
N1—C7—C8	116.5 (4)	O5—N2—C11	118.0 (5)
C13—C8—C9	120.9 (5)	O4—N2—C11	117.3 (5)
C13—C8—C7	123.2 (5)	O1—S1—O2	119.3 (3)
C9—C8—C7	115.9 (5)	O1—S1—N1	108.8 (3)
C8—C9—C10	120.1 (5)	O2—S1—N1	104.3 (2)
C8—C9—H9	120.0	O1—S1—C1	107.9 (3)
C10—C9—H9	120.0	O2—S1—C1	109.9 (2)
C11—C10—C9	117.8 (6)	N1—S1—C1	105.9 (3)
C11—C10—H10	121.1
C6—C1—C2—C3	−0.3 (8)	C10—C11—C12—C13	−0.6 (10)
S1—C1—C2—C3	−175.1 (5)	N2—C11—C12—C13	−178.1 (5)
C6—C1—C2—C14	−178.4 (6)	C9—C8—C13—C12	−2.2 (9)
S1—C1—C2—C14	6.7 (8)	C7—C8—C13—C12	178.4 (6)
C1—C2—C3—C4	1.4 (10)	C11—C12—C13—C8	1.2 (9)
C14—C2—C3—C4	179.6 (6)	O3—C7—N1—S1	0.5 (8)
C2—C3—C4—C5	−2.8 (11)	C8—C7—N1—S1	−178.6 (4)
C3—C4—C5—C6	3.0 (11)	C12—C11—N2—O5	7.1 (8)
C2—C1—C6—C5	0.7 (9)	C10—C11—N2—O5	−170.5 (6)
S1—C1—C6—C5	175.7 (5)	C12—C11—N2—O4	−172.3 (6)
C4—C5—C6—C1	−1.9 (10)	C10—C11—N2—O4	10.1 (9)
O3—C7—C8—C13	160.5 (6)	C7—N1—S1—O1	−53.9 (5)
N1—C7—C8—C13	−20.4 (8)	C7—N1—S1—O2	177.8 (4)
O3—C7—C8—C9	−18.9 (9)	C7—N1—S1—C1	61.8 (5)
N1—C7—C8—C9	160.3 (5)	C6—C1—S1—O1	14.8 (5)
C13—C8—C9—C10	2.6 (9)	C2—C1—S1—O1	−170.0 (4)
C7—C8—C9—C10	−178.0 (5)	C6—C1—S1—O2	146.4 (5)
C8—C9—C10—C11	−2.0 (10)	C2—C1—S1—O2	−38.4 (6)
C9—C10—C11—C12	1.0 (10)	C6—C1—S1—N1	−101.5 (5)
C9—C10—C11—N2	178.5 (6)	C2—C1—S1—N1	73.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.87 (3)	2.12 (4)	2.992 (6)	174 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.87 (3)	2.12 (4)	2.992 (6)	174 (5)

Symmetry code: (i) .