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

In the title compound, C(15)H(15)NO(3)S, the 2-methyl-phenyl ring bonded to the sulfonyl group is disordered with site-occupation factors of 0.75:0.25. The dihedral angles between the two aromatic rings are 67.6 (1) and 69.2 (1)° for the major and the minor occupied sites, respectively. In the crystal, mol-ecules are linked into centrosymmetric dimers by pairs of N-H⋯O hydrogen bonds.

Related literature

For background literature and similar structures, see: Gowda et al. (2010 ▶); Suchetan et al. (2010 ▶).

Experimental

Crystal data

C15H15NO3S

M = 289.34

Monoclinic,

a = 13.997 (1) Å

b = 14.165 (1) Å

c = 14.395 (2) Å

β = 96.955 (8)°

V = 2833.1 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 299 K

0.40 × 0.36 × 0.34 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.912, T max = 0.925

5920 measured reflections

2895 independent reflections

2281 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.114

S = 1.12

2895 reflections

251 parameters

9 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.26 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/S1600536810026735/bt5290sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026735/bt5290Isup2.hkl

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

C15H15NO3S	F(000) = 1216
Mr = 289.34	Dx = 1.357 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2699 reflections
a = 13.997 (1) Å	θ = 2.6–27.8°
b = 14.165 (1) Å	µ = 0.24 mm−1
c = 14.395 (2) Å	T = 299 K
β = 96.955 (8)°	Prism, colourless
V = 2833.1 (5) Å3	0.40 × 0.36 × 0.34 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2895 independent reflections
Radiation source: fine-focus sealed tube	2281 reflections with I > 2σ(I)
graphite	Rint = 0.015
Rotation method data acquisition using ω and phi scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −14→17
Tmin = 0.912, Tmax = 0.925	k = −17→12
5920 measured reflections	l = −17→17

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0707P)2] where P = (Fo2 + 2Fc2)/3
2895 reflections	(Δ/σ)max < 0.001
251 parameters	Δρmax = 0.30 e Å−3
9 restraints	Δρmin = −0.26 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	Occ. (<1)
C1A	0.1586 (2)	0.3862 (2)	0.2895 (2)	0.0392 (7)	0.75
C1B	0.1568 (6)	0.3398 (6)	0.2942 (6)	0.0354 (18)	0.25
C2A	0.13372 (16)	0.3021 (2)	0.2415 (2)	0.0506 (6)	0.75
C2B	0.1299 (5)	0.3961 (6)	0.2180 (5)	0.0528 (18)	0.25
C3A	0.0925 (6)	0.3103 (4)	0.1473 (4)	0.0680 (17)	0.75
H3A	0.0726	0.2567	0.1131	0.082*	0.75
C3B	0.0951 (16)	0.3438 (9)	0.1388 (10)	0.041 (3)	0.25
H3B	0.0742	0.3779	0.0849	0.050*	0.25
C4A	0.0817 (2)	0.3986 (3)	0.1061 (2)	0.0712 (8)	0.75
H4A	0.0543	0.4029	0.0441	0.085*	0.75
C4B	0.0886 (6)	0.2496 (8)	0.1325 (6)	0.066 (2)	0.25
H4B	0.0648	0.2220	0.0758	0.079*	0.25
C5A	0.1093 (2)	0.4781 (2)	0.1523 (2)	0.0650 (8)	0.75
H5A	0.1024	0.5363	0.1223	0.078*	0.75
C5B	0.1164 (7)	0.1931 (7)	0.2084 (7)	0.079 (3)	0.25
H5B	0.1133	0.1276	0.2056	0.095*	0.25
C6A	0.1483 (3)	0.4725 (3)	0.2459 (3)	0.0505 (8)	0.75
H6A	0.1675	0.5272	0.2788	0.061*	0.75
C6B	0.1493 (10)	0.2411 (8)	0.2890 (9)	0.050 (3)	0.25
H6B	0.1675	0.2062	0.3430	0.060*	0.25
C7	0.38609 (11)	0.39162 (11)	0.36903 (10)	0.0396 (3)
C8	0.47917 (10)	0.33980 (11)	0.37729 (10)	0.0390 (3)
C9	0.56650 (11)	0.38885 (13)	0.38842 (11)	0.0496 (4)
C10	0.65018 (12)	0.33451 (18)	0.39523 (14)	0.0675 (6)
H10	0.7094	0.3651	0.4045	0.081*
C11	0.64890 (13)	0.23848 (17)	0.38881 (14)	0.0712 (6)
H11	0.7064	0.2050	0.3933	0.085*
C12	0.56284 (14)	0.19138 (15)	0.37571 (13)	0.0614 (5)
H12	0.5614	0.1260	0.3699	0.074*
C13	0.47861 (12)	0.24202 (12)	0.37119 (11)	0.0479 (4)
H13	0.4201	0.2101	0.3639	0.057*
C14A	0.1486 (5)	0.2049 (3)	0.2834 (5)	0.0866 (18)	0.75
H14A	0.1053	0.1957	0.3295	0.104*	0.75
H14B	0.2138	0.1989	0.3124	0.104*	0.75
H14C	0.1362	0.1583	0.2351	0.104*	0.75
C14B	0.1351 (11)	0.4964 (9)	0.2142 (8)	0.062 (3)	0.25
H14D	0.1919	0.5176	0.2526	0.074*	0.25
H14E	0.0792	0.5231	0.2368	0.074*	0.25
H14F	0.1376	0.5160	0.1508	0.074*	0.25
C15	0.57390 (14)	0.49465 (14)	0.39237 (14)	0.0687 (6)
H15C	0.6380	0.5125	0.4176	0.082*
H15B	0.5288	0.5190	0.4316	0.082*
H15A	0.5596	0.5201	0.3304	0.082*
N1	0.31537 (9)	0.34845 (10)	0.41437 (9)	0.0439 (3)
H1N	0.3279 (12)	0.2983 (8)	0.4467 (11)	0.053*
O1	0.15903 (8)	0.32012 (10)	0.46446 (9)	0.0645 (4)
O2	0.20209 (10)	0.48187 (10)	0.43476 (10)	0.0743 (4)
O3	0.36933 (9)	0.46426 (9)	0.32707 (9)	0.0609 (4)
S1	0.20355 (3)	0.38584 (3)	0.40857 (3)	0.04381 (16)

	U11	U22	U33	U12	U13	U23
C1A	0.0344 (11)	0.0406 (16)	0.0446 (15)	0.0054 (14)	0.0126 (10)	0.0021 (15)
C1B	0.028 (3)	0.032 (5)	0.046 (4)	0.001 (4)	0.004 (3)	−0.011 (4)
C2A	0.0416 (13)	0.0475 (15)	0.0645 (17)	−0.0073 (11)	0.0139 (12)	−0.0012 (16)
C2B	0.045 (4)	0.076 (6)	0.038 (4)	0.008 (3)	0.005 (3)	0.002 (4)
C3A	0.0522 (19)	0.075 (5)	0.078 (3)	−0.018 (4)	0.015 (2)	−0.024 (3)
C3B	0.043 (5)	0.041 (8)	0.038 (5)	−0.008 (7)	−0.003 (4)	0.002 (5)
C4A	0.0545 (16)	0.110 (3)	0.0481 (16)	0.0103 (18)	0.0022 (13)	−0.0010 (18)
C4B	0.058 (5)	0.083 (7)	0.057 (5)	−0.022 (5)	0.011 (4)	−0.012 (5)
C5A	0.0680 (18)	0.076 (2)	0.0507 (15)	0.0261 (15)	0.0078 (13)	0.0176 (16)
C5B	0.076 (6)	0.065 (6)	0.098 (7)	−0.018 (5)	0.014 (5)	−0.041 (6)
C6A	0.0564 (17)	0.049 (2)	0.047 (2)	0.0174 (15)	0.0092 (15)	0.0061 (15)
C6B	0.049 (4)	0.046 (8)	0.054 (5)	−0.005 (6)	0.004 (3)	−0.012 (6)
C7	0.0404 (8)	0.0437 (9)	0.0353 (7)	−0.0031 (6)	0.0067 (6)	0.0002 (7)
C8	0.0363 (8)	0.0497 (9)	0.0318 (7)	−0.0026 (6)	0.0077 (6)	0.0028 (7)
C9	0.0449 (9)	0.0658 (11)	0.0392 (8)	−0.0119 (8)	0.0096 (7)	0.0006 (8)
C10	0.0349 (9)	0.1043 (17)	0.0642 (11)	−0.0074 (9)	0.0089 (8)	0.0060 (11)
C11	0.0480 (12)	0.0952 (17)	0.0733 (13)	0.0213 (11)	0.0186 (9)	0.0147 (12)
C12	0.0604 (11)	0.0623 (12)	0.0648 (11)	0.0151 (9)	0.0214 (9)	0.0044 (9)
C13	0.0445 (9)	0.0491 (9)	0.0518 (9)	−0.0002 (7)	0.0134 (7)	0.0028 (8)
C14A	0.103 (3)	0.043 (3)	0.118 (4)	−0.016 (3)	0.029 (3)	−0.001 (3)
C14B	0.081 (8)	0.045 (7)	0.058 (9)	0.014 (5)	0.004 (7)	0.007 (6)
C15	0.0678 (12)	0.0737 (14)	0.0661 (12)	−0.0303 (10)	0.0151 (9)	−0.0087 (10)
N1	0.0364 (7)	0.0493 (8)	0.0471 (7)	0.0055 (6)	0.0094 (6)	0.0136 (6)
O1	0.0443 (7)	0.0843 (9)	0.0688 (8)	0.0123 (6)	0.0224 (6)	0.0321 (7)
O2	0.0819 (10)	0.0615 (9)	0.0828 (10)	0.0224 (7)	0.0240 (8)	−0.0093 (7)
O3	0.0606 (8)	0.0533 (7)	0.0711 (8)	0.0053 (6)	0.0179 (6)	0.0228 (6)
S1	0.0401 (2)	0.0535 (3)	0.0392 (2)	0.01159 (17)	0.01069 (16)	0.00625 (17)

C1A—C6A	1.374 (4)	C7—C8	1.488 (2)
C1A—C2A	1.400 (3)	C8—C13	1.388 (2)
C1A—S1	1.753 (3)	C8—C9	1.398 (2)
C1B—C2B	1.372 (10)	C9—C10	1.395 (3)
C1B—C6B	1.403 (10)	C9—C15	1.503 (3)
C1B—S1	1.817 (8)	C10—C11	1.363 (3)
C2A—C3A	1.412 (7)	C10—H10	0.9300
C2A—C14A	1.507 (5)	C11—C12	1.370 (3)
C2B—C3B	1.397 (13)	C11—H11	0.9300
C2B—C14B	1.423 (13)	C12—C13	1.375 (2)
C3A—C4A	1.384 (5)	C12—H12	0.9300
C3A—H3A	0.9300	C13—H13	0.9300
C3B—C4B	1.340 (13)	C14A—H14A	0.9600
C3B—H3B	0.9300	C14A—H14B	0.9600
C4A—C5A	1.341 (5)	C14A—H14C	0.9600
C4A—H4A	0.9300	C14B—H14D	0.9600
C4B—C5B	1.372 (12)	C14B—H14E	0.9600
C4B—H4B	0.9300	C14B—H14F	0.9600
C5A—C6A	1.393 (4)	C15—H15C	0.9600
C5A—H5A	0.9300	C15—H15B	0.9600
C5B—C6B	1.375 (13)	C15—H15A	0.9600
C5B—H5B	0.9300	N1—S1	1.6449 (13)
C6A—H6A	0.9300	N1—H1N	0.856 (9)
C6B—H6B	0.9300	O1—S1	1.4226 (12)
C7—O3	1.2018 (18)	O2—S1	1.4123 (14)
C7—N1	1.3915 (19)
C6A—C1A—C2A	121.7 (3)	C9—C8—C7	120.59 (15)
C6A—C1A—S1	117.0 (3)	C10—C9—C8	116.66 (17)
C2A—C1A—S1	121.2 (2)	C10—C9—C15	119.61 (16)
C2B—C1B—C6B	121.7 (9)	C8—C9—C15	123.72 (16)
C2B—C1B—S1	123.3 (7)	C11—C10—C9	122.80 (17)
C6B—C1B—S1	115.0 (7)	C11—C10—H10	118.6
C1A—C2A—C3A	116.9 (3)	C9—C10—H10	118.6
C1A—C2A—C14A	124.4 (3)	C10—C11—C12	119.96 (17)
C3A—C2A—C14A	118.7 (4)	C10—C11—H11	120.0
C1B—C2B—C3B	112.2 (9)	C12—C11—H11	120.0
C1B—C2B—C14B	126.9 (8)	C11—C12—C13	119.16 (19)
C3B—C2B—C14B	120.9 (8)	C11—C12—H12	120.4
C4A—C3A—C2A	119.8 (5)	C13—C12—H12	120.4
C4A—C3A—H3A	120.1	C12—C13—C8	121.29 (17)
C2A—C3A—H3A	120.1	C12—C13—H13	119.4
C4B—C3B—C2B	126.7 (12)	C8—C13—H13	119.4
C4B—C3B—H3B	116.6	C2B—C14B—H14D	109.5
C2B—C3B—H3B	116.6	C2B—C14B—H14E	109.5
C5A—C4A—C3A	122.5 (4)	H14D—C14B—H14E	109.5
C5A—C4A—H4A	118.8	C2B—C14B—H14F	109.5
C3A—C4A—H4A	118.8	H14D—C14B—H14F	109.5
C3B—C4B—C5B	121.1 (9)	H14E—C14B—H14F	109.5
C3B—C4B—H4B	119.5	C9—C15—H15C	109.5
C5B—C4B—H4B	119.5	C9—C15—H15B	109.5
C4A—C5A—C6A	119.2 (3)	H15C—C15—H15B	109.5
C4A—C5A—H5A	120.4	C9—C15—H15A	109.5
C6A—C5A—H5A	120.4	H15C—C15—H15A	109.5
C4B—C5B—C6B	114.7 (9)	H15B—C15—H15A	109.5
C4B—C5B—H5B	122.6	C7—N1—S1	124.14 (11)
C6B—C5B—H5B	122.6	C7—N1—H1N	120.6 (12)
C1A—C6A—C5A	119.9 (4)	S1—N1—H1N	115.2 (12)
C1A—C6A—H6A	120.0	O2—S1—O1	117.24 (9)
C5A—C6A—H6A	120.0	O2—S1—N1	109.94 (8)
C5B—C6B—C1B	123.5 (10)	O1—S1—N1	103.88 (7)
C5B—C6B—H6B	118.3	O2—S1—C1A	104.07 (11)
C1B—C6B—H6B	118.3	O1—S1—C1A	115.14 (11)
O3—C7—N1	120.35 (14)	N1—S1—C1A	106.11 (10)
O3—C7—C8	125.34 (14)	O2—S1—C1B	124.9 (3)
N1—C7—C8	114.30 (13)	O1—S1—C1B	98.2 (3)
C13—C8—C9	120.09 (15)	N1—S1—C1B	99.6 (2)
C13—C8—C7	119.29 (13)
C6A—C1A—C2A—C3A	−3.5 (6)	C8—C9—C10—C11	1.9 (3)
S1—C1A—C2A—C3A	176.1 (4)	C15—C9—C10—C11	−177.57 (19)
C6A—C1A—C2A—C14A	176.2 (4)	C9—C10—C11—C12	−0.4 (3)
S1—C1A—C2A—C14A	−4.2 (5)	C10—C11—C12—C13	−1.4 (3)
C6B—C1B—C2B—C3B	0.4 (16)	C11—C12—C13—C8	1.6 (3)
S1—C1B—C2B—C3B	−179.1 (12)	C9—C8—C13—C12	−0.1 (2)
C6B—C1B—C2B—C14B	−179.3 (12)	C7—C8—C13—C12	178.09 (14)
S1—C1B—C2B—C14B	1.2 (13)	O3—C7—N1—S1	5.0 (2)
C1A—C2A—C3A—C4A	2.3 (9)	C8—C7—N1—S1	−174.44 (10)
C14A—C2A—C3A—C4A	−177.4 (6)	C7—N1—S1—O2	−54.19 (15)
C1B—C2B—C3B—C4B	−1(3)	C7—N1—S1—O1	179.57 (13)
C14B—C2B—C3B—C4B	178.4 (18)	C7—N1—S1—C1A	57.78 (17)
C2A—C3A—C4A—C5A	0.1 (9)	C7—N1—S1—C1B	78.5 (3)
C2B—C3B—C4B—C5B	1(3)	C6A—C1A—S1—O2	10.4 (3)
C3A—C4A—C5A—C6A	−1.5 (6)	C2A—C1A—S1—O2	−169.2 (2)
C3B—C4B—C5B—C6B	1(2)	C6A—C1A—S1—O1	140.2 (2)
C2A—C1A—C6A—C5A	2.2 (5)	C2A—C1A—S1—O1	−39.5 (3)
S1—C1A—C6A—C5A	−177.4 (3)	C6A—C1A—S1—N1	−105.6 (3)
C4A—C5A—C6A—C1A	0.3 (5)	C2A—C1A—S1—N1	74.8 (2)
C4B—C5B—C6B—C1B	−1.7 (18)	C6A—C1A—S1—C1B	179.8 (10)
C2B—C1B—C6B—C5B	1.1 (18)	C2A—C1A—S1—C1B	0.2 (7)
S1—C1B—C6B—C5B	−179.4 (10)	C2B—C1B—S1—O2	11.0 (8)
O3—C7—C8—C13	−139.43 (17)	C6B—C1B—S1—O2	−168.6 (7)
N1—C7—C8—C13	39.97 (19)	C2B—C1B—S1—O1	142.7 (6)
O3—C7—C8—C9	38.8 (2)	C6B—C1B—S1—O1	−36.9 (8)
N1—C7—C8—C9	−141.84 (14)	C2B—C1B—S1—N1	−111.7 (7)
C13—C8—C9—C10	−1.6 (2)	C6B—C1B—S1—N1	68.8 (8)
C7—C8—C9—C10	−179.76 (14)	C2B—C1B—S1—C1A	−1.6 (5)
C13—C8—C9—C15	177.84 (16)	C6B—C1B—S1—C1A	178.9 (14)
C7—C8—C9—C15	−0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86 (1)	2.10 (1)	2.9531 (17)	172 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86 (1)	2.10 (1)	2.9531 (17)	172 (2)

Symmetry code: (i) .