4-Methyl-N-[(S)-1-phenyl-eth-yl]benzene-sulfonamide.

In the title compound, C(15)H(17)NO(2)S, the dihedral angle between the aromatic rings is 14.47 (8)°. The mol-ecule is bent at the N atom, with a C-SO2-NH-C torsion angle of 79.06 (13)°. In the crystal structure, the sulfonamide groups are hydrogen bonded via N-H⋯O links, forming chains of mol-ecules along the crystallographic b axis. π-π inter-actions [centroid-centroid distance = 3.81 (3) Å] also occur.

Related literature

For general background to sulfonamides, see: Siddiqui et al. (2008 ▶) and literature cited therein; Padeiskaya & Polukhina (1974 ▶). For the anti­microbial properties of sulfonamides and their applications in medical practice, see: Mashkovskii (1987 ▶); Zhungietu & Granik, (2000 ▶). For chemical aspects of related compounds, see: Liu et al. (2009a ▶,b ▶); Seong et al. (1998 ▶). For related structures, see: Deng & Hu (2005 ▶); Zhu et al. (2008 ▶); Chatterjee et al. (1982 ▶); Ghosh et al. (1991 ▶); Takasuka & Nakai, (2001 ▶). For spectroscopic data for the title compound, see: Georgy et al. (2009 ▶).

Experimental

Crystal data

C15H17NO2S

M = 275.36

Monoclinic,

a = 8.1588 (4) Å

b = 10.1498 (4) Å

c = 8.9242 (5) Å

β = 105.545 (4)°

V = 711.98 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.76 × 0.55 × 0.38 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.881, T max = 0.933

10843 measured reflections

2950 independent reflections

2864 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.076

S = 1.05

2950 reflections

176 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 1388 Friedel pairs

Flack parameter: −0.02 (5)

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810032113/si2286sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032113/si2286Isup2.hkl

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

C15H17NO2S	F(000) = 292
Mr = 275.36	Dx = 1.284 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 10843 reflections
a = 8.1588 (4) Å	θ = 2.4–26.9°
b = 10.1498 (4) Å	µ = 0.23 mm−1
c = 8.9242 (5) Å	T = 296 K
β = 105.545 (4)°	Plane graphite, colorless
V = 711.98 (6) Å3	0.76 × 0.55 × 0.38 mm
Z = 2

Stoe IPDS 2 diffractometer	2950 independent reflections
Radiation source: fine-focus sealed tube	2864 reflections with I > 2σ(I)
graphite	Rint = 0.027
rotation method scans	θmax = 26.5°, θmin = 2.4°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −10→10
Tmin = 0.881, Tmax = 0.933	k = −12→12
10843 measured reflections	l = −11→11

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)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.076	w = 1/[σ2(Fo2) + (0.0563P)2 + 0.0201P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2950 reflections	Δρmax = 0.17 e Å−3
176 parameters	Δρmin = −0.23 e Å−3
2 restraints	Absolute structure: Flack (1983), 1388 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.02 (5)

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	0.69009 (17)	0.77118 (14)	0.68328 (15)	0.0428 (3)
C2	0.67635 (19)	0.88063 (14)	0.77051 (17)	0.0476 (3)
H2	0.6034	0.9491	0.7269	0.057*
C3	0.7724 (2)	0.88734 (17)	0.92370 (18)	0.0535 (3)
H3	0.7633	0.9609	0.9831	0.064*
C4	0.8815 (2)	0.78666 (18)	0.98963 (19)	0.0553 (4)
C5	0.8956 (2)	0.6792 (2)	0.9000 (2)	0.0609 (4)
H5	0.9708	0.6119	0.9432	0.073*
C6	0.8002 (2)	0.66945 (17)	0.7473 (2)	0.0546 (3)
H6	0.8096	0.5958	0.6882	0.066*
C7	0.9778 (3)	0.7926 (3)	1.1598 (2)	0.0814 (6)
H7A	1.0469	0.8706	1.1789	0.098*
H7B	1.0491	0.7163	1.1864	0.098*
H7C	0.8984	0.7948	1.2221	0.098*
C8	0.25591 (18)	0.69454 (16)	0.54631 (17)	0.0492 (3)
H8	0.2031	0.7677	0.4788	0.059*
C9	0.1317 (2)	0.5803 (2)	0.5145 (3)	0.0721 (5)
H9A	0.1025	0.5591	0.4057	0.087*
H9B	0.0308	0.6043	0.5437	0.087*
H9C	0.1833	0.5050	0.5739	0.087*
C10	0.29391 (16)	0.74216 (18)	0.71331 (15)	0.0466 (3)
C11	0.2449 (2)	0.86701 (19)	0.7442 (2)	0.0638 (4)
H11	0.1885	0.9212	0.6627	0.077*
C12	0.2791 (3)	0.9121 (2)	0.8955 (3)	0.0831 (6)
H12	0.2453	0.9964	0.9151	0.100*
C13	0.3624 (3)	0.8335 (3)	1.0168 (2)	0.0803 (6)
H13	0.3844	0.8639	1.1186	0.096*
C14	0.4129 (3)	0.7105 (2)	0.9874 (2)	0.0714 (6)
H14	0.4712	0.6575	1.0695	0.086*
C15	0.3784 (2)	0.66387 (18)	0.83688 (18)	0.0568 (4)
H15	0.4121	0.5792	0.8184	0.068*
N1	0.40634 (17)	0.65258 (12)	0.49794 (14)	0.0465 (3)
O1	0.48302 (17)	0.87632 (11)	0.44036 (12)	0.0612 (3)
O2	0.65796 (18)	0.68619 (15)	0.40456 (14)	0.0684 (3)
S1	0.55950 (4)	0.75139 (4)	0.49215 (3)	0.04629 (10)
H16	0.4401 (19)	0.5744 (16)	0.5177 (19)	0.044 (4)*

	U11	U22	U33	U12	U13	U23
C1	0.0486 (6)	0.0399 (7)	0.0399 (6)	−0.0036 (5)	0.0121 (5)	0.0028 (5)
C2	0.0549 (7)	0.0398 (7)	0.0448 (7)	−0.0017 (6)	0.0075 (6)	−0.0004 (6)
C3	0.0611 (8)	0.0499 (8)	0.0464 (7)	−0.0085 (7)	0.0093 (6)	−0.0067 (6)
C4	0.0486 (7)	0.0667 (11)	0.0466 (7)	−0.0086 (6)	0.0058 (6)	0.0061 (6)
C5	0.0541 (8)	0.0640 (10)	0.0610 (9)	0.0129 (7)	0.0093 (7)	0.0120 (8)
C6	0.0596 (8)	0.0492 (8)	0.0561 (8)	0.0090 (7)	0.0172 (7)	0.0004 (7)
C7	0.0795 (12)	0.1006 (17)	0.0517 (9)	−0.0085 (11)	−0.0040 (8)	0.0086 (9)
C8	0.0502 (7)	0.0509 (7)	0.0418 (7)	0.0045 (6)	0.0044 (5)	−0.0014 (6)
C9	0.0593 (9)	0.0869 (14)	0.0674 (11)	−0.0175 (9)	0.0124 (8)	−0.0182 (10)
C10	0.0478 (6)	0.0465 (7)	0.0449 (6)	−0.0002 (6)	0.0113 (5)	−0.0038 (7)
C11	0.0646 (9)	0.0576 (10)	0.0690 (10)	0.0131 (8)	0.0177 (8)	−0.0074 (8)
C12	0.0906 (14)	0.0773 (14)	0.0898 (15)	0.0018 (11)	0.0388 (12)	−0.0340 (12)
C13	0.0881 (14)	0.1013 (17)	0.0577 (10)	−0.0286 (12)	0.0306 (10)	−0.0272 (11)
C14	0.0815 (11)	0.0865 (15)	0.0437 (8)	−0.0241 (10)	0.0127 (8)	0.0035 (8)
C15	0.0693 (9)	0.0506 (8)	0.0489 (8)	−0.0047 (7)	0.0131 (7)	0.0035 (7)
N1	0.0589 (6)	0.0347 (6)	0.0439 (6)	−0.0013 (5)	0.0105 (5)	−0.0056 (5)
O1	0.0858 (8)	0.0432 (6)	0.0457 (5)	−0.0070 (5)	0.0022 (5)	0.0079 (5)
O2	0.0826 (8)	0.0785 (8)	0.0519 (6)	−0.0063 (7)	0.0317 (6)	−0.0120 (6)
S1	0.06240 (19)	0.04072 (16)	0.03579 (15)	−0.00478 (15)	0.01324 (12)	−0.00162 (14)

C1—C2	1.378 (2)	C9—H9A	0.9600
C1—C6	1.387 (2)	C9—H9B	0.9600
C1—S1	1.7638 (13)	C9—H9C	0.9600
C2—C3	1.383 (2)	C10—C11	1.379 (3)
C2—H2	0.9300	C10—C15	1.384 (2)
C3—C4	1.379 (2)	C11—C12	1.381 (3)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.375 (3)	C12—C13	1.370 (4)
C4—C7	1.512 (2)	C12—H12	0.9300
C5—C6	1.380 (2)	C13—C14	1.362 (4)
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—C15	1.381 (2)
C7—H7A	0.9600	C14—H14	0.9300
C7—H7B	0.9600	C15—H15	0.9300
C7—H7C	0.9600	N1—S1	1.6138 (13)
C8—N1	1.469 (2)	N1—H16	0.843 (15)
C8—C9	1.516 (2)	O1—S1	1.4339 (12)
C8—C10	1.5177 (19)	O2—S1	1.4251 (13)
C8—H8	0.9800
C2—C1—C6	120.59 (13)	H9A—C9—H9B	109.5
C2—C1—S1	121.23 (11)	C8—C9—H9C	109.5
C6—C1—S1	118.06 (11)	H9A—C9—H9C	109.5
C1—C2—C3	119.18 (14)	H9B—C9—H9C	109.5
C1—C2—H2	120.4	C11—C10—C15	118.51 (15)
C3—C2—H2	120.4	C11—C10—C8	119.70 (15)
C4—C3—C2	121.00 (15)	C15—C10—C8	121.78 (16)
C4—C3—H3	119.5	C10—C11—C12	120.45 (19)
C2—C3—H3	119.5	C10—C11—H11	119.8
C5—C4—C3	118.99 (14)	C12—C11—H11	119.8
C5—C4—C7	120.90 (17)	C13—C12—C11	120.5 (2)
C3—C4—C7	120.05 (17)	C13—C12—H12	119.8
C4—C5—C6	121.19 (16)	C11—C12—H12	119.8
C4—C5—H5	119.4	C14—C13—C12	119.55 (19)
C6—C5—H5	119.4	C14—C13—H13	120.2
C5—C6—C1	119.03 (16)	C12—C13—H13	120.2
C5—C6—H6	120.5	C13—C14—C15	120.6 (2)
C1—C6—H6	120.5	C13—C14—H14	119.7
C4—C7—H7A	109.5	C15—C14—H14	119.7
C4—C7—H7B	109.5	C14—C15—C10	120.44 (18)
H7A—C7—H7B	109.5	C14—C15—H15	119.8
C4—C7—H7C	109.5	C10—C15—H15	119.8
H7A—C7—H7C	109.5	C8—N1—S1	122.98 (10)
H7B—C7—H7C	109.5	C8—N1—H16	117.6 (11)
N1—C8—C9	106.99 (14)	S1—N1—H16	112.3 (11)
N1—C8—C10	114.46 (12)	O2—S1—O1	119.63 (8)
C9—C8—C10	112.21 (15)	O2—S1—N1	106.51 (8)
N1—C8—H8	107.6	O1—S1—N1	106.62 (7)
C9—C8—H8	107.6	O2—S1—C1	107.46 (7)
C10—C8—H8	107.6	O1—S1—C1	107.99 (7)
C8—C9—H9A	109.5	N1—S1—C1	108.18 (6)
C8—C9—H9B	109.5
C6—C1—C2—C3	−0.7 (2)	C11—C12—C13—C14	0.5 (3)
S1—C1—C2—C3	175.22 (11)	C12—C13—C14—C15	−1.1 (3)
C1—C2—C3—C4	0.2 (2)	C13—C14—C15—C10	0.9 (3)
C2—C3—C4—C5	0.8 (2)	C11—C10—C15—C14	−0.2 (3)
C2—C3—C4—C7	−176.55 (16)	C8—C10—C15—C14	179.21 (15)
C3—C4—C5—C6	−1.4 (3)	C9—C8—N1—S1	172.13 (12)
C7—C4—C5—C6	175.96 (18)	C10—C8—N1—S1	−62.90 (17)
C4—C5—C6—C1	0.9 (3)	C8—N1—S1—O2	−165.68 (12)
C2—C1—C6—C5	0.2 (2)	C8—N1—S1—O1	−36.88 (13)
S1—C1—C6—C5	−175.89 (13)	C8—N1—S1—C1	79.06 (13)
N1—C8—C10—C11	122.94 (16)	C2—C1—S1—O2	145.43 (12)
C9—C8—C10—C11	−114.90 (18)	C6—C1—S1—O2	−38.50 (14)
N1—C8—C10—C15	−56.5 (2)	C2—C1—S1—O1	15.11 (14)
C9—C8—C10—C15	65.69 (19)	C6—C1—S1—O1	−168.83 (12)
C15—C10—C11—C12	−0.3 (3)	C2—C1—S1—N1	−99.93 (12)
C8—C10—C11—C12	−179.74 (18)	C6—C1—S1—N1	76.13 (12)
C10—C11—C12—C13	0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H16···O1i	0.84 (2)	2.11 (2)	2.9519 (17)	178.(1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H16⋯O1i	0.84 (2)	2.11 (2)	2.9519 (17)	178 (1)

Symmetry code: (i) .