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

In the title compound, C(15)H(15)NO(3)S, the conformation of the N-H bond in the C-SO(2)-NH-C(O) segment is anti to the C=O bond. Further, the conformation of the C=O bond is syn to the ortho-methyl group in the benzoyl ring. The dihedral angle between the sulfonyl benzene ring and the -SO(2)-NH-C-O segment is 87.1 (1)° and that between the sulfonyl and the benzoyl benzene rings is 58.2 (1)°. In the crystal structure, mol-ecules are linked by pairs of N-H⋯O(S) hydrogen bonds, forming inversion dimers.

Related literature

For background to our study of the effect of ring and side-chain substituents on the crystal structures of N-aromatic sulfonamides and for similar structures, see: Gowda et al. (2010 ▶); Suchetan et al. (2010 ▶).

Experimental

Crystal data

C15H15NO3S

M = 289.34

Triclinic,

a = 6.4097 (8) Å

b = 10.433 (1) Å

c = 11.258 (1) Å

α = 79.17 (1)°

β = 74.34 (1)°

γ = 85.15 (2)°

V = 711.54 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 299 K

0.30 × 0.20 × 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 = 0.933, T max = 0.959

4725 measured reflections

2872 independent reflections

2387 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.107

S = 1.06

2872 reflections

186 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.35 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 datablocks I, global. DOI: 10.1107/S1600536810019513/bq2213sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019513/bq2213Isup2.hkl

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

C15H15NO3S	Z = 2
Mr = 289.34	F(000) = 304
Triclinic, P1	Dx = 1.350 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4097 (8) Å	Cell parameters from 2355 reflections
b = 10.433 (1) Å	θ = 2.5–27.8°
c = 11.258 (1) Å	µ = 0.23 mm−1
α = 79.17 (1)°	T = 299 K
β = 74.34 (1)°	Rod, colorless
γ = 85.15 (2)°	0.30 × 0.20 × 0.18 mm
V = 711.54 (13) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2872 independent reflections
Radiation source: fine-focus sealed tube	2387 reflections with I > 2σ(I)
graphite	Rint = 0.013
Rotation method data acquisition using ω and phi scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −8→7
Tmin = 0.933, Tmax = 0.959	k = −9→13
4725 measured reflections	l = −13→14

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0434P)2 + 0.3252P] where P = (Fo2 + 2Fc2)/3
2872 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 0.27 e Å−3
1 restraint	Δρmin = −0.35 e Å−3

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
S1	0.72322 (8)	0.15911 (5)	0.01004 (4)	0.04175 (15)
O1	0.9097 (2)	0.12090 (14)	−0.08160 (13)	0.0543 (4)
O2	0.5303 (2)	0.20184 (15)	−0.02716 (14)	0.0562 (4)
O3	0.3654 (2)	0.09970 (16)	0.24228 (16)	0.0646 (5)
N1	0.6788 (3)	0.02815 (15)	0.12042 (15)	0.0412 (4)
H1N	0.786 (2)	−0.0260 (17)	0.113 (2)	0.049*
C1	0.7964 (3)	0.27802 (18)	0.08116 (17)	0.0394 (4)
C2	0.6662 (3)	0.38915 (19)	0.0973 (2)	0.0487 (5)
H2	0.5389	0.4012	0.0714	0.058*
C3	0.7279 (4)	0.4821 (2)	0.1526 (2)	0.0589 (6)
H3	0.6434	0.5584	0.1612	0.071*
C4	0.9127 (4)	0.4638 (2)	0.1953 (2)	0.0548 (6)
C5	1.0396 (4)	0.3503 (2)	0.1788 (2)	0.0570 (6)
H5	1.1642	0.3365	0.2074	0.068*
C6	0.9848 (3)	0.2584 (2)	0.1211 (2)	0.0508 (5)
H6	1.0728	0.1840	0.1089	0.061*
C7	0.5092 (3)	0.01727 (19)	0.22766 (18)	0.0402 (4)
C8	0.5191 (3)	−0.10252 (19)	0.32282 (18)	0.0415 (4)
C9	0.6634 (3)	−0.1125 (2)	0.39775 (19)	0.0473 (5)
C10	0.6505 (4)	−0.2220 (3)	0.4924 (2)	0.0663 (7)
H10	0.7442	−0.2313	0.5440	0.080*
C11	0.5017 (5)	−0.3158 (3)	0.5106 (2)	0.0767 (8)
H11	0.4960	−0.3878	0.5741	0.092*
C12	0.3617 (5)	−0.3045 (3)	0.4360 (3)	0.0758 (8)
H12	0.2620	−0.3687	0.4486	0.091*
C13	0.3690 (4)	−0.1980 (2)	0.3425 (2)	0.0575 (6)
H13	0.2732	−0.1898	0.2923	0.069*
C14	0.9773 (5)	0.5629 (3)	0.2596 (3)	0.0849 (9)
H14A	0.8955	0.6432	0.2458	0.102*
H14B	1.1292	0.5782	0.2262	0.102*
H14C	0.9482	0.5302	0.3479	0.102*
C15	0.8194 (4)	−0.0075 (3)	0.3825 (2)	0.0658 (7)
H15A	0.9429	−0.0169	0.3136	0.079*
H15B	0.8659	−0.0150	0.4578	0.079*
H15C	0.7492	0.0765	0.3663	0.079*

	U11	U22	U33	U12	U13	U23
S1	0.0464 (3)	0.0408 (3)	0.0362 (3)	0.00360 (19)	−0.0112 (2)	−0.00359 (19)
O1	0.0642 (9)	0.0521 (8)	0.0364 (7)	0.0070 (7)	−0.0004 (7)	−0.0051 (6)
O2	0.0581 (9)	0.0609 (9)	0.0542 (9)	0.0045 (7)	−0.0287 (7)	−0.0036 (7)
O3	0.0505 (9)	0.0703 (11)	0.0600 (10)	0.0194 (8)	−0.0056 (8)	−0.0015 (8)
N1	0.0450 (9)	0.0362 (8)	0.0394 (9)	0.0031 (7)	−0.0082 (7)	−0.0052 (7)
C1	0.0388 (9)	0.0361 (9)	0.0386 (10)	0.0007 (7)	−0.0070 (8)	−0.0005 (8)
C2	0.0494 (11)	0.0409 (11)	0.0511 (12)	0.0089 (9)	−0.0124 (9)	−0.0017 (9)
C3	0.0708 (15)	0.0391 (11)	0.0573 (14)	0.0089 (10)	−0.0047 (12)	−0.0073 (10)
C4	0.0679 (14)	0.0458 (11)	0.0440 (12)	−0.0166 (10)	−0.0018 (10)	−0.0031 (9)
C5	0.0492 (12)	0.0588 (13)	0.0636 (14)	−0.0106 (10)	−0.0162 (11)	−0.0059 (11)
C6	0.0417 (11)	0.0451 (11)	0.0648 (14)	0.0037 (9)	−0.0139 (10)	−0.0101 (10)
C7	0.0387 (10)	0.0450 (10)	0.0393 (10)	−0.0024 (8)	−0.0130 (8)	−0.0083 (8)
C8	0.0446 (10)	0.0440 (10)	0.0345 (9)	0.0009 (8)	−0.0067 (8)	−0.0094 (8)
C9	0.0470 (11)	0.0563 (12)	0.0385 (10)	0.0101 (9)	−0.0110 (9)	−0.0129 (9)
C10	0.0794 (17)	0.0770 (17)	0.0417 (12)	0.0211 (14)	−0.0220 (12)	−0.0096 (11)
C11	0.111 (2)	0.0579 (15)	0.0474 (14)	0.0018 (15)	−0.0091 (15)	0.0068 (11)
C12	0.100 (2)	0.0588 (15)	0.0610 (16)	−0.0226 (14)	−0.0091 (15)	−0.0003 (12)
C13	0.0670 (14)	0.0553 (13)	0.0506 (13)	−0.0135 (11)	−0.0145 (11)	−0.0060 (10)
C14	0.115 (2)	0.0692 (17)	0.0694 (18)	−0.0326 (16)	−0.0078 (17)	−0.0204 (14)
C15	0.0528 (13)	0.0923 (19)	0.0612 (15)	−0.0041 (12)	−0.0248 (12)	−0.0202 (13)

S1—O2	1.4210 (15)	C7—C8	1.495 (3)
S1—O1	1.4351 (15)	C8—C13	1.390 (3)
S1—N1	1.6519 (17)	C8—C9	1.396 (3)
S1—C1	1.754 (2)	C9—C10	1.400 (3)
O3—C7	1.206 (2)	C9—C15	1.500 (3)
N1—C7	1.383 (2)	C10—C11	1.374 (4)
N1—H1N	0.849 (9)	C10—H10	0.9300
C1—C2	1.381 (3)	C11—C12	1.369 (4)
C1—C6	1.385 (3)	C11—H11	0.9300
C2—C3	1.381 (3)	C12—C13	1.374 (3)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.381 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—H14A	0.9600
C4—C5	1.392 (3)	C14—H14B	0.9600
C4—C14	1.509 (3)	C14—H14C	0.9600
C5—C6	1.371 (3)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600
O2—S1—O1	118.80 (9)	C13—C8—C9	120.8 (2)
O2—S1—N1	110.35 (9)	C13—C8—C7	118.47 (18)
O1—S1—N1	103.52 (8)	C9—C8—C7	120.44 (18)
O2—S1—C1	109.33 (9)	C8—C9—C10	117.4 (2)
O1—S1—C1	109.09 (9)	C8—C9—C15	121.8 (2)
N1—S1—C1	104.75 (9)	C10—C9—C15	120.7 (2)
C7—N1—S1	124.66 (14)	C11—C10—C9	121.2 (2)
C7—N1—H1N	121.5 (15)	C11—C10—H10	119.4
S1—N1—H1N	112.5 (15)	C9—C10—H10	119.4
C2—C1—C6	120.86 (19)	C12—C11—C10	120.6 (2)
C2—C1—S1	119.99 (16)	C12—C11—H11	119.7
C6—C1—S1	119.15 (15)	C10—C11—H11	119.7
C3—C2—C1	119.0 (2)	C11—C12—C13	119.8 (3)
C3—C2—H2	120.5	C11—C12—H12	120.1
C1—C2—H2	120.5	C13—C12—H12	120.1
C4—C3—C2	121.3 (2)	C12—C13—C8	120.2 (2)
C4—C3—H3	119.4	C12—C13—H13	119.9
C2—C3—H3	119.4	C8—C13—H13	119.9
C3—C4—C5	118.4 (2)	C4—C14—H14A	109.5
C3—C4—C14	121.6 (2)	C4—C14—H14B	109.5
C5—C4—C14	120.0 (2)	H14A—C14—H14B	109.5
C6—C5—C4	121.4 (2)	C4—C14—H14C	109.5
C6—C5—H5	119.3	H14A—C14—H14C	109.5
C4—C5—H5	119.3	H14B—C14—H14C	109.5
C5—C6—C1	119.06 (19)	C9—C15—H15A	109.5
C5—C6—H6	120.5	C9—C15—H15B	109.5
C1—C6—H6	120.5	H15A—C15—H15B	109.5
O3—C7—N1	121.68 (18)	C9—C15—H15C	109.5
O3—C7—C8	123.12 (18)	H15A—C15—H15C	109.5
N1—C7—C8	115.21 (16)	H15B—C15—H15C	109.5
O2—S1—N1—C7	−49.84 (18)	S1—C1—C6—C5	−178.79 (17)
O1—S1—N1—C7	−177.98 (16)	S1—N1—C7—O3	8.0 (3)
C1—S1—N1—C7	67.73 (17)	S1—N1—C7—C8	−171.57 (13)
O2—S1—C1—C2	2.47 (19)	O3—C7—C8—C13	70.2 (3)
O1—S1—C1—C2	133.91 (16)	N1—C7—C8—C13	−110.2 (2)
N1—S1—C1—C2	−115.79 (17)	O3—C7—C8—C9	−104.1 (2)
O2—S1—C1—C6	−177.85 (16)	N1—C7—C8—C9	75.4 (2)
O1—S1—C1—C6	−46.42 (18)	C13—C8—C9—C10	0.1 (3)
N1—S1—C1—C6	63.89 (18)	C7—C8—C9—C10	174.35 (18)
C6—C1—C2—C3	0.9 (3)	C13—C8—C9—C15	−176.9 (2)
S1—C1—C2—C3	−179.44 (16)	C7—C8—C9—C15	−2.7 (3)
C1—C2—C3—C4	−2.1 (3)	C8—C9—C10—C11	0.1 (3)
C2—C3—C4—C5	1.5 (3)	C15—C9—C10—C11	177.2 (2)
C2—C3—C4—C14	−177.9 (2)	C9—C10—C11—C12	0.0 (4)
C3—C4—C5—C6	0.3 (3)	C10—C11—C12—C13	−0.3 (4)
C14—C4—C5—C6	179.8 (2)	C11—C12—C13—C8	0.6 (4)
C4—C5—C6—C1	−1.5 (3)	C9—C8—C13—C12	−0.5 (3)
C2—C1—C6—C5	0.9 (3)	C7—C8—C13—C12	−174.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.85 (1)	2.08 (1)	2.917 (2)	167 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.85 (1)	2.08 (1)	2.917 (2)	167 (2)

Symmetry code: (i) .