2-Methyl-N-(3-methyl-benzo-yl)benzene-sulfonamide.

In the title compound, C(15)H(15)NO(3)S, the sulfonyl and amide-bound benzene rings are oriented at dihedral angles of 83.1 (1) and 22.5 (3)°, respectively, with the almost planar S-N-C=O segment (r.m.s. deviation = 0.003 Å). The dihedral angle between the two benzene rings is 74.8 (1)°. In the crystal structure, pairs of 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. (2009 ▶); Suchetan et al. (2010 ▶).

Experimental

Crystal data

C15H15NO3S

M = 289.34

Monoclinic,

a = 18.023 (4) Å

b = 12.045 (3) Å

c = 17.335 (4) Å

β = 127.67 (1)°

V = 2978.7 (12) Å3

Z = 8

Cu Kα radiation

μ = 1.99 mm−1

T = 299 K

0.30 × 0.18 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

10158 measured reflections

2654 independent reflections

2219 reflections with I > 2σ(I)

R int = 0.072

3 standard reflections every 120 min intensity decay: 1.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.176

S = 1.08

2654 reflections

187 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: n class="CellLine">CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); 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/S1600536810002254/ci5020sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002254/ci5020Isup2.hkl

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

C15H15NO3S	F(000) = 1216
Mr = 289.34	Dx = 1.290 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 18.023 (4) Å	θ = 4.8–20.5°
b = 12.045 (3) Å	µ = 1.99 mm−1
c = 17.335 (4) Å	T = 299 K
β = 127.67 (1)°	Prism, colourless
V = 2978.7 (12) Å3	0.30 × 0.18 × 0.18 mm
Z = 8

Enraf–Nonius CAD-4 diffractometer	Rint = 0.072
Radiation source: fine-focus sealed tube	θmax = 67.0°, θmin = 4.6°
graphite	h = −21→21
ω/2θ scans	k = −14→14
10158 measured reflections	l = −20→20
2654 independent reflections	3 standard reflections every 120 min
2219 reflections with I > 2σ(I)	intensity decay: 1.5%

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) = 0.176	w = 1/[σ2(Fo2) + (0.0835P)2 + 3.6838P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.007
2654 reflections	Δρmax = 0.41 e Å−3
187 parameters	Δρmin = −0.28 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0016 (2)

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	0.39278 (5)	0.37414 (6)	0.48527 (5)	0.0536 (3)
O1	0.41777 (17)	0.48868 (19)	0.50971 (18)	0.0718 (7)
O2	0.39810 (16)	0.3050 (2)	0.55495 (15)	0.0708 (7)
O3	0.41415 (18)	0.15139 (19)	0.4361 (2)	0.0767 (7)
N1	0.46572 (18)	0.3289 (2)	0.4653 (2)	0.0586 (7)
H1N	0.499 (2)	0.381 (2)	0.472 (3)	0.070*
C1	0.2810 (2)	0.3633 (2)	0.3733 (2)	0.0499 (7)
C2	0.2518 (2)	0.4330 (2)	0.2951 (2)	0.0592 (8)
C3	0.1604 (3)	0.4177 (3)	0.2116 (3)	0.0777 (10)
H3	0.1381	0.4625	0.1578	0.093*
C4	0.1016 (3)	0.3391 (3)	0.2053 (3)	0.0773 (10)
H4	0.0407	0.3319	0.1480	0.093*
C5	0.1322 (2)	0.2713 (3)	0.2829 (3)	0.0715 (9)
H5	0.0924	0.2182	0.2787	0.086*
C6	0.2223 (2)	0.2827 (3)	0.3672 (2)	0.0590 (8)
H6	0.2440	0.2364	0.4200	0.071*
C7	0.4670 (2)	0.2184 (3)	0.4415 (2)	0.0600 (8)
C8	0.5356 (2)	0.1891 (3)	0.4240 (2)	0.0605 (8)
C9	0.5736 (2)	0.2662 (3)	0.3972 (2)	0.0674 (9)
H9	0.5589	0.3411	0.3933	0.081*
C10	0.6332 (3)	0.2327 (4)	0.3764 (3)	0.0878 (12)
C11	0.6549 (4)	0.1236 (5)	0.3850 (5)	0.1154 (19)
H11	0.6935	0.1000	0.3695	0.138*
C12	0.6215 (4)	0.0456 (4)	0.4160 (5)	0.1150 (18)
H12	0.6407	−0.0280	0.4251	0.138*
C13	0.5602 (3)	0.0787 (3)	0.4328 (3)	0.0810 (11)
H13	0.5348	0.0266	0.4503	0.097*
C14	0.3103 (3)	0.5223 (3)	0.2966 (3)	0.0810 (11)
H14A	0.3714	0.4934	0.3237	0.097*
H14B	0.3161	0.5831	0.3357	0.097*
H14C	0.2809	0.5476	0.2313	0.097*
C15	0.6712 (4)	0.3156 (5)	0.3441 (4)	0.1154 (17)
H15A	0.7328	0.3381	0.3991	0.138*
H15B	0.6308	0.3793	0.3168	0.138*
H15C	0.6744	0.2826	0.2958	0.138*

	U11	U22	U33	U12	U13	U23
S1	0.0517 (5)	0.0539 (5)	0.0577 (5)	−0.0039 (3)	0.0348 (4)	−0.0060 (3)
O1	0.0712 (14)	0.0582 (13)	0.0930 (16)	−0.0136 (11)	0.0538 (14)	−0.0249 (12)
O2	0.0653 (14)	0.0888 (17)	0.0578 (12)	−0.0003 (12)	0.0374 (11)	0.0127 (11)
O3	0.0791 (16)	0.0542 (13)	0.1081 (19)	−0.0074 (11)	0.0629 (15)	−0.0032 (12)
N1	0.0540 (15)	0.0563 (15)	0.0753 (16)	−0.0050 (11)	0.0445 (13)	−0.0054 (13)
C1	0.0525 (16)	0.0454 (15)	0.0561 (15)	0.0004 (12)	0.0353 (14)	−0.0020 (12)
C2	0.0656 (19)	0.0518 (16)	0.0650 (18)	0.0056 (14)	0.0423 (16)	0.0049 (14)
C3	0.081 (2)	0.079 (2)	0.0598 (19)	0.013 (2)	0.0361 (19)	0.0094 (17)
C4	0.061 (2)	0.081 (2)	0.064 (2)	−0.0008 (18)	0.0243 (17)	−0.0085 (18)
C5	0.0584 (19)	0.068 (2)	0.080 (2)	−0.0135 (16)	0.0380 (18)	−0.0138 (18)
C6	0.0602 (18)	0.0550 (17)	0.0639 (18)	−0.0037 (14)	0.0391 (15)	−0.0003 (14)
C7	0.0608 (18)	0.0506 (17)	0.0637 (18)	0.0005 (14)	0.0355 (16)	−0.0008 (14)
C8	0.0585 (17)	0.0582 (18)	0.0635 (18)	0.0009 (14)	0.0367 (15)	−0.0061 (14)
C9	0.075 (2)	0.0611 (19)	0.074 (2)	−0.0045 (16)	0.0503 (19)	−0.0077 (16)
C10	0.090 (3)	0.103 (3)	0.092 (3)	−0.013 (2)	0.067 (2)	−0.021 (2)
C11	0.116 (4)	0.110 (4)	0.173 (5)	−0.014 (3)	0.115 (4)	−0.047 (4)
C12	0.118 (4)	0.086 (3)	0.170 (5)	0.006 (3)	0.103 (4)	−0.031 (3)
C13	0.084 (3)	0.057 (2)	0.107 (3)	0.0001 (18)	0.062 (2)	−0.0099 (19)
C14	0.093 (3)	0.067 (2)	0.095 (3)	0.0019 (19)	0.063 (2)	0.019 (2)
C15	0.120 (4)	0.144 (5)	0.127 (4)	−0.023 (3)	0.099 (4)	−0.009 (3)

S1—O2	1.421 (2)	C7—C8	1.484 (4)
S1—O1	1.433 (2)	C8—C13	1.381 (5)
S1—N1	1.643 (3)	C8—C9	1.391 (5)
S1—C1	1.750 (3)	C9—C10	1.386 (5)
O3—C7	1.209 (4)	C9—H9	0.93
N1—C7	1.398 (4)	C10—C11	1.353 (7)
N1—H1N	0.83 (2)	C10—C15	1.499 (6)
C1—C6	1.392 (4)	C11—C12	1.387 (7)
C1—C2	1.396 (4)	C11—H11	0.93
C2—C3	1.388 (5)	C12—C13	1.364 (6)
C2—C14	1.494 (5)	C12—H12	0.93
C3—C4	1.376 (6)	C13—H13	0.93
C3—H3	0.93	C14—H14A	0.96
C4—C5	1.368 (5)	C14—H14B	0.96
C4—H4	0.93	C14—H14C	0.96
C5—C6	1.375 (5)	C15—H15A	0.96
C5—H5	0.93	C15—H15B	0.96
C6—H6	0.93	C15—H15C	0.96
O2—S1—O1	117.85 (15)	C13—C8—C9	119.3 (3)
O2—S1—N1	109.70 (15)	C13—C8—C7	117.2 (3)
O1—S1—N1	103.55 (14)	C9—C8—C7	123.4 (3)
O2—S1—C1	109.46 (14)	C10—C9—C8	120.7 (4)
O1—S1—C1	109.93 (14)	C10—C9—H9	119.7
N1—S1—C1	105.55 (14)	C8—C9—H9	119.7
C7—N1—S1	122.6 (2)	C11—C10—C9	118.2 (4)
C7—N1—H1N	128 (3)	C11—C10—C15	121.4 (4)
S1—N1—H1N	109 (3)	C9—C10—C15	120.4 (4)
C6—C1—C2	121.9 (3)	C10—C11—C12	122.4 (4)
C6—C1—S1	116.3 (2)	C10—C11—H11	118.8
C2—C1—S1	121.9 (2)	C12—C11—H11	118.8
C3—C2—C1	115.8 (3)	C13—C12—C11	119.0 (4)
C3—C2—C14	119.3 (3)	C13—C12—H12	120.5
C1—C2—C14	124.9 (3)	C11—C12—H12	120.5
C4—C3—C2	122.7 (3)	C12—C13—C8	120.3 (4)
C4—C3—H3	118.6	C12—C13—H13	119.8
C2—C3—H3	118.6	C8—C13—H13	119.8
C5—C4—C3	120.3 (3)	C2—C14—H14A	109.5
C5—C4—H4	119.9	C2—C14—H14B	109.5
C3—C4—H4	119.9	H14A—C14—H14B	109.5
C4—C5—C6	119.3 (3)	C2—C14—H14C	109.5
C4—C5—H5	120.3	H14A—C14—H14C	109.5
C6—C5—H5	120.3	H14B—C14—H14C	109.5
C5—C6—C1	120.0 (3)	C10—C15—H15A	109.5
C5—C6—H6	120.0	C10—C15—H15B	109.5
C1—C6—H6	120.0	H15A—C15—H15B	109.5
O3—C7—N1	120.2 (3)	C10—C15—H15C	109.5
O3—C7—C8	122.8 (3)	H15A—C15—H15C	109.5
N1—C7—C8	117.0 (3)	H15B—C15—H15C	109.5
O2—S1—N1—C7	51.6 (3)	C2—C1—C6—C5	−1.1 (5)
O1—S1—N1—C7	178.3 (3)	S1—C1—C6—C5	177.6 (3)
C1—S1—N1—C7	−66.2 (3)	S1—N1—C7—O3	−1.1 (5)
O2—S1—C1—C6	−7.5 (3)	S1—N1—C7—C8	179.1 (2)
O1—S1—C1—C6	−138.4 (2)	O3—C7—C8—C13	−20.9 (5)
N1—S1—C1—C6	110.5 (2)	N1—C7—C8—C13	158.9 (3)
O2—S1—C1—C2	171.3 (2)	O3—C7—C8—C9	157.4 (3)
O1—S1—C1—C2	40.4 (3)	N1—C7—C8—C9	−22.8 (5)
N1—S1—C1—C2	−70.7 (3)	C13—C8—C9—C10	2.1 (5)
C6—C1—C2—C3	0.8 (5)	C7—C8—C9—C10	−176.3 (3)
S1—C1—C2—C3	−178.0 (2)	C8—C9—C10—C11	−1.5 (6)
C6—C1—C2—C14	179.1 (3)	C8—C9—C10—C15	177.8 (4)
S1—C1—C2—C14	0.4 (5)	C9—C10—C11—C12	−1.6 (8)
C1—C2—C3—C4	0.0 (5)	C15—C10—C11—C12	179.1 (5)
C14—C2—C3—C4	−178.5 (4)	C10—C11—C12—C13	4.1 (9)
C2—C3—C4—C5	−0.3 (6)	C11—C12—C13—C8	−3.3 (8)
C3—C4—C5—C6	0.0 (6)	C9—C8—C13—C12	0.4 (6)
C4—C5—C6—C1	0.7 (5)	C7—C8—C13—C12	178.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.83 (2)	2.06 (2)	2.884 (4)	179 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.83 (2)	2.06 (2)	2.884 (4)	179 (4)

Symmetry code: (i) .