N-(2,5-Dimethyl-phen-yl)benzene-sulfonamide.

In the title compound, C(14)H(15)NO(2)S, the dihedral angle between the aromatic rings is 40.4 (1)° relative to each other. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds occur.

Related literature

For the preparation of the title compound, see: Gowda et al. (2005 ▶). For related structures, see: Gowda et al. (2008 ▶; 2009 ▶). For bond-length data for other aryl sulfonamides, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C14H15NO2S

M = 261.33

Monoclinic,

a = 10.523 (1) Å

b = 8.5631 (7) Å

c = 15.135 (2) Å

β = 101.86 (1)°

V = 1334.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 299 K

0.44 × 0.40 × 0.34 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.903, T max = 0.924

5236 measured reflections

2727 independent reflections

2221 reflections with I > 2σ(I)

R int = 0.010

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.108

S = 1.10

2727 reflections

169 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 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/S1600536809041841/pk2200sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041841/pk2200Isup2.hkl

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

C14H15NO2S	F(000) = 552
Mr = 261.33	Dx = 1.301 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2374 reflections
a = 10.523 (1) Å	θ = 2.6–27.8°
b = 8.5631 (7) Å	µ = 0.24 mm−1
c = 15.135 (2) Å	T = 299 K
β = 101.86 (1)°	Prism, colourless
V = 1334.7 (2) Å3	0.44 × 0.40 × 0.34 mm
Z = 4

Oxford Diffraction Xcalibur (TM) Single Crystal X-ray Diffractometer with Sapphire CCD Detector.	2727 independent reflections
Radiation source: fine-focus sealed tube	2221 reflections with I > 2σ(I)
graphite	Rint = 0.010
Detector resolution: 0 pixels mm-1	θmax = 26.4°, θmin = 2.6°
Rotation method data acquisition using ω and phi scans.	h = −10→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −10→7
Tmin = 0.903, Tmax = 0.924	l = −17→18
5236 measured reflections

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.108	w = 1/[σ2(Fo2) + (0.0568P)2 + 0.2974P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
2727 reflections	Δρmax = 0.27 e Å−3
169 parameters	Δρmin = −0.25 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0149 (18)

Experimental. 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	0.78193 (4)	0.44572 (5)	−0.00630 (3)	0.03753 (16)
O1	0.88777 (11)	0.35489 (14)	−0.02510 (9)	0.0504 (3)
O2	0.68808 (12)	0.37259 (15)	0.03523 (9)	0.0476 (3)
N1	0.84891 (13)	0.58790 (18)	0.05948 (10)	0.0417 (4)
H1N	0.9148 (19)	0.619 (2)	0.0428 (13)	0.050*
C1	0.70021 (15)	0.53338 (19)	−0.10743 (11)	0.0381 (4)
C2	0.57570 (16)	0.5897 (2)	−0.11257 (13)	0.0474 (4)
H2	0.5335	0.5753	−0.0649	0.057*
C3	0.5152 (2)	0.6672 (3)	−0.18942 (16)	0.0647 (6)
H3	0.4315	0.7057	−0.1937	0.078*
C4	0.5778 (2)	0.6880 (3)	−0.25983 (16)	0.0722 (7)
H4	0.5361	0.7404	−0.3115	0.087*
C5	0.7015 (2)	0.6322 (3)	−0.25444 (14)	0.0672 (6)
H5	0.7429	0.6467	−0.3025	0.081*
C6	0.76449 (19)	0.5545 (2)	−0.17803 (13)	0.0513 (5)
H6	0.8484	0.5170	−0.1739	0.062*
C7	0.76772 (16)	0.7043 (2)	0.08868 (12)	0.0437 (4)
C8	0.7529 (2)	0.8517 (2)	0.04985 (15)	0.0607 (5)
C9	0.6695 (3)	0.9543 (3)	0.0839 (2)	0.0831 (8)
H9	0.6550	1.0538	0.0593	0.100*
C10	0.6091 (3)	0.9108 (3)	0.1524 (2)	0.0825 (8)
H10	0.5540	0.9815	0.1722	0.099*
C11	0.62731 (19)	0.7668 (3)	0.19244 (15)	0.0622 (6)
C12	0.70773 (16)	0.6642 (2)	0.15926 (13)	0.0486 (4)
H12	0.7221	0.5655	0.1849	0.058*
C13	0.8207 (3)	0.9011 (3)	−0.0238 (2)	0.0899 (8)
H13A	0.9091	0.8655	−0.0099	0.108*
H13B	0.8193	1.0129	−0.0285	0.108*
H13C	0.7771	0.8565	−0.0801	0.108*
C14	0.5648 (2)	0.7236 (4)	0.27002 (18)	0.0873 (9)
H14A	0.5622	0.8136	0.3074	0.105*
H14B	0.6143	0.6425	0.3050	0.105*
H14C	0.4780	0.6873	0.2471	0.105*

	U11	U22	U33	U12	U13	U23
S1	0.0331 (2)	0.0359 (2)	0.0443 (3)	0.00200 (16)	0.00952 (16)	0.00318 (17)
O1	0.0408 (7)	0.0461 (7)	0.0665 (8)	0.0092 (5)	0.0160 (6)	0.0016 (6)
O2	0.0451 (7)	0.0453 (7)	0.0557 (7)	−0.0032 (5)	0.0178 (6)	0.0076 (6)
N1	0.0323 (7)	0.0464 (8)	0.0455 (8)	−0.0026 (6)	0.0059 (6)	0.0000 (6)
C1	0.0367 (8)	0.0365 (9)	0.0401 (9)	−0.0039 (7)	0.0057 (6)	−0.0013 (7)
C2	0.0361 (9)	0.0486 (10)	0.0563 (11)	−0.0009 (8)	0.0065 (7)	0.0057 (8)
C3	0.0464 (11)	0.0637 (13)	0.0759 (15)	−0.0004 (10)	−0.0062 (10)	0.0161 (11)
C4	0.0747 (15)	0.0708 (15)	0.0588 (13)	−0.0115 (12)	−0.0145 (11)	0.0211 (11)
C5	0.0848 (16)	0.0733 (15)	0.0435 (11)	−0.0153 (13)	0.0134 (10)	0.0075 (10)
C6	0.0522 (10)	0.0533 (11)	0.0513 (11)	−0.0013 (9)	0.0174 (8)	0.0003 (9)
C7	0.0362 (8)	0.0413 (9)	0.0479 (10)	−0.0017 (7)	−0.0048 (7)	−0.0071 (8)
C8	0.0646 (13)	0.0414 (10)	0.0685 (14)	−0.0071 (9)	−0.0041 (10)	−0.0037 (9)
C9	0.0940 (19)	0.0369 (11)	0.105 (2)	0.0072 (12)	−0.0096 (16)	−0.0086 (12)
C10	0.0697 (15)	0.0679 (16)	0.106 (2)	0.0097 (13)	0.0097 (14)	−0.0323 (15)
C11	0.0484 (11)	0.0638 (14)	0.0715 (14)	−0.0028 (10)	0.0057 (9)	−0.0311 (11)
C12	0.0402 (9)	0.0514 (11)	0.0507 (10)	−0.0020 (8)	0.0016 (7)	−0.0129 (8)
C13	0.113 (2)	0.0534 (14)	0.097 (2)	−0.0199 (15)	0.0091 (16)	0.0187 (13)
C14	0.0714 (15)	0.109 (2)	0.0881 (18)	−0.0067 (15)	0.0315 (13)	−0.0484 (16)

S1—O2	1.4205 (12)	C7—C8	1.387 (3)
S1—O1	1.4340 (12)	C7—C12	1.391 (3)
S1—N1	1.6377 (15)	C8—C9	1.412 (3)
S1—C1	1.7620 (17)	C8—C13	1.503 (4)
N1—C7	1.440 (2)	C9—C10	1.374 (4)
N1—H1N	0.828 (19)	C9—H9	0.9300
C1—C2	1.383 (2)	C10—C11	1.370 (4)
C1—C6	1.389 (2)	C10—H10	0.9300
C2—C3	1.376 (3)	C11—C12	1.384 (3)
C2—H2	0.9300	C11—C14	1.505 (3)
C3—C4	1.375 (3)	C12—H12	0.9300
C3—H3	0.9300	C13—H13A	0.9600
C4—C5	1.373 (3)	C13—H13B	0.9600
C4—H4	0.9300	C13—H13C	0.9600
C5—C6	1.380 (3)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
O2—S1—O1	119.19 (8)	C12—C7—N1	117.14 (16)
O2—S1—N1	108.07 (8)	C7—C8—C9	115.8 (2)
O1—S1—N1	105.61 (8)	C7—C8—C13	122.8 (2)
O2—S1—C1	108.22 (8)	C9—C8—C13	121.4 (2)
O1—S1—C1	108.61 (8)	C10—C9—C8	121.7 (2)
N1—S1—C1	106.47 (8)	C10—C9—H9	119.2
C7—N1—S1	119.53 (11)	C8—C9—H9	119.2
C7—N1—H1N	117.4 (15)	C11—C10—C9	122.3 (2)
S1—N1—H1N	109.5 (14)	C11—C10—H10	118.9
C2—C1—C6	121.13 (16)	C9—C10—H10	118.9
C2—C1—S1	119.01 (13)	C10—C11—C12	116.8 (2)
C6—C1—S1	119.72 (13)	C10—C11—C14	121.5 (2)
C3—C2—C1	118.92 (18)	C12—C11—C14	121.7 (2)
C3—C2—H2	120.5	C11—C12—C7	122.0 (2)
C1—C2—H2	120.5	C11—C12—H12	119.0
C4—C3—C2	120.4 (2)	C7—C12—H12	119.0
C4—C3—H3	119.8	C8—C13—H13A	109.5
C2—C3—H3	119.8	C8—C13—H13B	109.5
C5—C4—C3	120.5 (2)	H13A—C13—H13B	109.5
C5—C4—H4	119.7	C8—C13—H13C	109.5
C3—C4—H4	119.7	H13A—C13—H13C	109.5
C4—C5—C6	120.3 (2)	H13B—C13—H13C	109.5
C4—C5—H5	119.9	C11—C14—H14A	109.5
C6—C5—H5	119.9	C11—C14—H14B	109.5
C5—C6—C1	118.76 (19)	H14A—C14—H14B	109.5
C5—C6—H6	120.6	C11—C14—H14C	109.5
C1—C6—H6	120.6	H14A—C14—H14C	109.5
C8—C7—C12	121.37 (18)	H14B—C14—H14C	109.5
C8—C7—N1	121.47 (18)
O2—S1—N1—C7	−53.36 (15)	S1—C1—C6—C5	−175.98 (16)
O1—S1—N1—C7	178.05 (13)	S1—N1—C7—C8	−102.82 (18)
C1—S1—N1—C7	62.70 (15)	S1—N1—C7—C12	78.98 (18)
O2—S1—C1—C2	31.30 (16)	C12—C7—C8—C9	−2.6 (3)
O1—S1—C1—C2	162.03 (14)	N1—C7—C8—C9	179.28 (17)
N1—S1—C1—C2	−84.66 (15)	C12—C7—C8—C13	177.4 (2)
O2—S1—C1—C6	−153.10 (14)	N1—C7—C8—C13	−0.8 (3)
O1—S1—C1—C6	−22.37 (16)	C7—C8—C9—C10	1.2 (3)
N1—S1—C1—C6	90.94 (15)	C13—C8—C9—C10	−178.8 (2)
C6—C1—C2—C3	0.2 (3)	C8—C9—C10—C11	0.8 (4)
S1—C1—C2—C3	175.78 (15)	C9—C10—C11—C12	−1.5 (3)
C1—C2—C3—C4	0.1 (3)	C9—C10—C11—C14	177.4 (2)
C2—C3—C4—C5	−0.1 (4)	C10—C11—C12—C7	0.0 (3)
C3—C4—C5—C6	−0.1 (4)	C14—C11—C12—C7	−178.80 (18)
C4—C5—C6—C1	0.4 (3)	C8—C7—C12—C11	2.1 (3)
C2—C1—C6—C5	−0.5 (3)	N1—C7—C12—C11	−179.74 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.828 (19)	2.16 (2)	2.9634 (19)	163.3 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.828 (19)	2.16 (2)	2.9634 (19)	163.3 (19)

Symmetry code: (i) .