N-Phenyl-N-(prop-2-en-1-yl)benzene-sulfonamide.

In the mol-ecule of the title compound, C(15)H(15)NO(2)S, the dihedral angle between the two phenyl rings is 41.8 (3)°. The S atom has a distorted tetra-hedral environment. In the crystal structure, C-H⋯O hydrogen bonds link the molecules into a ribbon-like structure along [010].

Related literature

For details of the biological activity and pharmaceutical applications of sulfonamide derivatives, see: Kazmierski et al. (2004 ▶); Beate et al. (1998 ▶); Skrzipczyk et al. (1994 ▶). For related structures, see: Arshad et al. (2009 ▶); Khan et al. (2009 ▶).

Experimental

Crystal data

C15H15NO2S

M = 273.35

Monoclinic,

a = 11.6302 (8) Å

b = 5.7041 (4) Å

c = 21.9408 (14) Å

β = 103.535 (4)°

V = 1415.12 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 295 K

0.25 × 0.12 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.958, T max = 0.978

9448 measured reflections

2467 independent reflections

1803 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.245

S = 0.93

2467 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.58 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810013152/ci5071sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013152/ci5071Isup2.hkl

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

C15H15NO2S	F(000) = 576
Mr = 273.35	Dx = 1.283 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3368 reflections
a = 11.6302 (8) Å	θ = 2.4–22.3°
b = 5.7041 (4) Å	µ = 0.23 mm−1
c = 21.9408 (14) Å	T = 295 K
β = 103.535 (4)°	Plate, colourless
V = 1415.12 (17) Å3	0.25 × 0.12 × 0.08 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2467 independent reflections
Radiation source: fine-focus sealed tube	1803 reflections with I > 2σ(I)
graphite	Rint = 0.046
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.958, Tmax = 0.978	k = −6→5
9448 measured reflections	l = −26→26

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.245	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.1687P)2 + 2.1422P] where P = (Fo2 + 2Fc2)/3
2467 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.58 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.69888 (9)	−0.0377 (2)	0.71607 (5)	0.0425 (4)
N1	0.6478 (3)	0.1073 (6)	0.65082 (15)	0.0421 (9)
C9	0.7280 (4)	−0.0195 (9)	0.5639 (2)	0.0500 (11)
H9	0.6824	−0.1545	0.5615	0.060*
C10	0.7692 (3)	0.1656 (8)	0.77270 (17)	0.0398 (10)
C13	0.8729 (5)	0.5034 (11)	0.8566 (2)	0.0683 (15)
H13	0.9082	0.6188	0.8848	0.082*
C3	0.4412 (6)	0.5309 (14)	0.5687 (3)	0.092 (2)
H3A	0.4626	0.6644	0.5930	0.111*
H3B	0.3918	0.5436	0.5288	0.111*
C4	0.7260 (4)	0.1466 (8)	0.60926 (17)	0.0407 (10)
C1	0.5584 (4)	0.2901 (9)	0.6524 (2)	0.0504 (11)
H1A	0.5114	0.2434	0.6815	0.060*
H1B	0.5982	0.4356	0.6675	0.060*
C11	0.8892 (4)	0.2012 (9)	0.7843 (2)	0.0525 (12)
H11	0.9351	0.1128	0.7633	0.063*
C5	0.7939 (4)	0.3460 (8)	0.6128 (2)	0.0512 (11)
H5	0.7929	0.4574	0.6437	0.061*
C2	0.4799 (4)	0.3294 (11)	0.5901 (2)	0.0631 (14)
H2	0.4569	0.1994	0.5645	0.076*
C15	0.7010 (4)	0.2992 (10)	0.80332 (19)	0.0548 (13)
H15	0.6199	0.2745	0.7958	0.066*
C7	0.8644 (4)	0.2144 (11)	0.5249 (2)	0.0616 (14)
H7	0.9106	0.2384	0.4962	0.074*
C6	0.8631 (5)	0.3801 (10)	0.5706 (2)	0.0616 (13)
H6	0.9090	0.5148	0.5728	0.074*
C14	0.7545 (5)	0.4699 (11)	0.8452 (2)	0.0686 (16)
H14	0.7090	0.5619	0.8655	0.082*
O2	0.7865 (3)	−0.1951 (6)	0.70389 (14)	0.0545 (9)
O1	0.5986 (3)	−0.1260 (6)	0.73525 (15)	0.0582 (9)
C8	0.7983 (5)	0.0159 (10)	0.5219 (2)	0.0616 (14)
H8	0.8005	−0.0963	0.4914	0.074*
C12	0.9411 (4)	0.3693 (11)	0.8272 (2)	0.0641 (15)
H12	1.0226	0.3915	0.8361	0.077*

	U11	U22	U33	U12	U13	U23
S1	0.0455 (7)	0.0354 (7)	0.0488 (7)	0.0000 (5)	0.0153 (5)	0.0014 (4)
N1	0.0414 (18)	0.042 (2)	0.0431 (18)	0.0055 (16)	0.0106 (14)	−0.0030 (16)
C9	0.057 (3)	0.046 (3)	0.047 (2)	−0.001 (2)	0.014 (2)	−0.011 (2)
C10	0.037 (2)	0.044 (3)	0.041 (2)	0.0036 (18)	0.0143 (16)	0.0044 (18)
C13	0.070 (4)	0.075 (4)	0.055 (3)	−0.012 (3)	0.005 (2)	−0.016 (3)
C3	0.096 (5)	0.112 (6)	0.070 (4)	0.050 (4)	0.020 (3)	0.021 (4)
C4	0.045 (2)	0.039 (2)	0.037 (2)	0.0094 (19)	0.0076 (16)	0.0005 (17)
C1	0.044 (2)	0.057 (3)	0.051 (2)	0.010 (2)	0.0128 (18)	−0.005 (2)
C11	0.040 (2)	0.064 (3)	0.056 (3)	0.000 (2)	0.0167 (19)	0.002 (2)
C5	0.059 (3)	0.036 (3)	0.061 (3)	0.005 (2)	0.019 (2)	−0.003 (2)
C2	0.052 (3)	0.079 (4)	0.057 (3)	0.016 (3)	0.010 (2)	0.002 (3)
C15	0.039 (2)	0.080 (4)	0.045 (2)	0.006 (2)	0.0099 (18)	−0.011 (2)
C7	0.058 (3)	0.078 (4)	0.053 (3)	0.014 (3)	0.022 (2)	0.015 (3)
C6	0.066 (3)	0.049 (3)	0.074 (3)	0.002 (3)	0.026 (3)	0.013 (3)
C14	0.062 (3)	0.086 (4)	0.056 (3)	0.013 (3)	0.008 (2)	−0.022 (3)
O2	0.0622 (19)	0.0412 (19)	0.0631 (19)	0.0148 (15)	0.0206 (15)	0.0029 (15)
O1	0.0529 (18)	0.055 (2)	0.070 (2)	−0.0140 (16)	0.0216 (15)	0.0053 (17)
C8	0.074 (3)	0.065 (4)	0.050 (3)	0.012 (3)	0.022 (2)	−0.008 (2)
C12	0.039 (2)	0.091 (4)	0.061 (3)	−0.018 (3)	0.009 (2)	−0.003 (3)

S1—O1	1.422 (3)	C1—C2	1.473 (6)
S1—O2	1.429 (3)	C1—H1A	0.97
S1—N1	1.640 (3)	C1—H1B	0.97
S1—C10	1.756 (4)	C11—C12	1.380 (7)
N1—C4	1.448 (5)	C11—H11	0.93
N1—C1	1.479 (5)	C5—C6	1.377 (7)
C9—C4	1.379 (6)	C5—H5	0.93
C9—C8	1.382 (7)	C2—H2	0.93
C9—H9	0.93	C15—C14	1.382 (7)
C10—C11	1.374 (6)	C15—H15	0.93
C10—C15	1.382 (6)	C7—C8	1.361 (8)
C13—C14	1.354 (8)	C7—C6	1.379 (7)
C13—C12	1.368 (8)	C7—H7	0.93
C13—H13	0.93	C6—H6	0.93
C3—C2	1.283 (8)	C14—H14	0.93
C3—H3A	0.93	C8—H8	0.93
C3—H3B	0.93	C12—H12	0.93
C4—C5	1.376 (6)
O1—S1—O2	120.2 (2)	H1A—C1—H1B	107.9
O1—S1—N1	106.41 (19)	C10—C11—C12	119.4 (4)
O2—S1—N1	106.38 (18)	C10—C11—H11	120.3
O1—S1—C10	107.66 (19)	C12—C11—H11	120.3
O2—S1—C10	108.22 (19)	C4—C5—C6	119.8 (5)
N1—S1—C10	107.3 (2)	C4—C5—H5	120.1
C4—N1—C1	117.0 (3)	C6—C5—H5	120.1
C4—N1—S1	118.4 (3)	C3—C2—C1	124.3 (6)
C1—N1—S1	116.6 (3)	C3—C2—H2	117.8
C4—C9—C8	119.6 (5)	C1—C2—H2	117.8
C4—C9—H9	120.2	C14—C15—C10	119.4 (4)
C8—C9—H9	120.2	C14—C15—H15	120.3
C11—C10—C15	120.2 (4)	C10—C15—H15	120.3
C11—C10—S1	120.9 (3)	C8—C7—C6	120.2 (5)
C15—C10—S1	118.9 (3)	C8—C7—H7	119.9
C14—C13—C12	120.7 (5)	C6—C7—H7	119.9
C14—C13—H13	119.6	C5—C6—C7	120.0 (5)
C12—C13—H13	119.6	C5—C6—H6	120.0
C2—C3—H3A	120.0	C7—C6—H6	120.0
C2—C3—H3B	120.0	C13—C14—C15	120.1 (5)
H3A—C3—H3B	120.0	C13—C14—H14	119.9
C5—C4—C9	120.2 (4)	C15—C14—H14	119.9
C5—C4—N1	121.9 (4)	C7—C8—C9	120.3 (5)
C9—C4—N1	117.9 (4)	C7—C8—H8	119.9
C2—C1—N1	111.8 (4)	C9—C8—H8	119.9
C2—C1—H1A	109.3	C13—C12—C11	120.1 (4)
N1—C1—H1A	109.3	C13—C12—H12	120.0
C2—C1—H1B	109.3	C11—C12—H12	120.0
N1—C1—H1B	109.3
O1—S1—N1—C4	−158.8 (3)	C4—N1—C1—C2	58.4 (5)
O2—S1—N1—C4	−29.5 (4)	S1—N1—C1—C2	−153.1 (4)
C10—S1—N1—C4	86.2 (3)	C15—C10—C11—C12	0.8 (7)
O1—S1—N1—C1	53.2 (4)	S1—C10—C11—C12	177.3 (4)
O2—S1—N1—C1	−177.5 (3)	C9—C4—C5—C6	0.5 (7)
C10—S1—N1—C1	−61.9 (3)	N1—C4—C5—C6	−177.3 (4)
O1—S1—C10—C11	150.3 (4)	N1—C1—C2—C3	−141.8 (6)
O2—S1—C10—C11	19.0 (4)	C11—C10—C15—C14	0.5 (7)
N1—S1—C10—C11	−95.5 (4)	S1—C10—C15—C14	−176.1 (4)
O1—S1—C10—C15	−33.1 (4)	C4—C5—C6—C7	−0.1 (7)
O2—S1—C10—C15	−164.5 (4)	C8—C7—C6—C5	−0.7 (8)
N1—S1—C10—C15	81.1 (4)	C12—C13—C14—C15	−0.1 (9)
C8—C9—C4—C5	−0.2 (7)	C10—C15—C14—C13	−0.9 (8)
C8—C9—C4—N1	177.7 (4)	C6—C7—C8—C9	1.0 (8)
C1—N1—C4—C5	55.6 (5)	C4—C9—C8—C7	−0.6 (7)
S1—N1—C4—C5	−92.3 (4)	C14—C13—C12—C11	1.5 (9)
C1—N1—C4—C9	−122.2 (4)	C10—C11—C12—C13	−1.8 (8)
S1—N1—C4—C9	89.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1i	0.97	2.57	3.427 (6)	147
C5—H5···O2ii	0.93	2.39	3.307 (6)	167
C15—H15···O1i	0.93	2.54	3.415 (6)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O1i	0.97	2.57	3.427 (6)	147
C5—H5⋯O2ii	0.93	2.39	3.307 (6)	167
C15—H15⋯O1i	0.93	2.54	3.415 (6)	158

Symmetry codes: (i) ; (ii) .