N-(2,3-Dimethyl-phen-yl)benzene-sulfonamide.

In the crystal structure of the title compound, C(14)H(15)NO(2)S, the amino H atom is trans to one of the O atoms of the SO(2) group. Furthermore, the N-H bond is anti to the ortho- and meta-methyl groups of the aromatic ring. The two aromatic rings are tilted relative to each other by 64.8 (1)°. The mol-ecules form zigzag chains along the a axis via inter-molecular N-H⋯O hydrogen bonds.

Related literature

For related literature, see: Gelbrich et al. (2007 ▶); Gowda et al. (2005 ▶); Gowda et al. (2008a ▶,b ▶,c ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C14H15NO2S

M = 261.33

Orthorhombic,

a = 6.3969 (5) Å

b = 8.8767 (6) Å

c = 23.082 (2) Å

V = 1310.67 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 299 (2) K

0.50 × 0.30 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.889, T max = 0.958

5869 measured reflections

2611 independent reflections

2200 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.094

S = 1.07

2611 reflections

168 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 1060 Friedel pairs

Flack parameter: −0.04 (9)

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002098/bt2853sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002098/bt2853Isup2.hkl

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

C14H15NO2S	F(000) = 552
Mr = 261.33	Dx = 1.324 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2432 reflections
a = 6.3969 (5) Å	θ = 2.3–27.7°
b = 8.8767 (6) Å	µ = 0.24 mm−1
c = 23.082 (2) Å	T = 299 K
V = 1310.67 (18) Å3	Rod, colourless
Z = 4	0.50 × 0.30 × 0.18 mm

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2611 independent reflections
Radiation source: fine-focus sealed tube	2200 reflections with I > 2σ(I)
graphite	Rint = 0.014
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 3.3°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −7→7
Tmin = 0.889, Tmax = 0.958	k = −5→11
5869 measured reflections	l = −13→28

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0525P)2 + 0.1566P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.025
2611 reflections	Δρmax = 0.20 e Å−3
168 parameters	Δρmin = −0.19 e Å−3
0 restraints	Absolute structure: Flack (1983), 1060 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.04 (9)

Experimental. CrysAlis RED (Oxford Diffraction, 2007) 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
C1	0.2823 (3)	−0.0378 (2)	0.43543 (9)	0.0389 (5)
C2	0.4720 (4)	−0.0422 (3)	0.46456 (11)	0.0507 (6)
H2	0.5124	0.0374	0.4882	0.061*
C3	0.5998 (4)	−0.1662 (3)	0.45797 (13)	0.0651 (7)
H3	0.7262	−0.1708	0.4778	0.078*
C4	0.5424 (5)	−0.2816 (3)	0.42263 (14)	0.0701 (9)
H4	0.6285	−0.3655	0.4189	0.084*
C5	0.3566 (6)	−0.2746 (3)	0.39226 (13)	0.0740 (9)
H5	0.3206	−0.3519	0.3670	0.089*
C6	0.2245 (5)	−0.1532 (3)	0.39934 (11)	0.0564 (6)
H6	0.0974	−0.1496	0.3798	0.068*
C7	0.2683 (4)	0.2922 (2)	0.36164 (9)	0.0419 (5)
C8	0.1257 (4)	0.3805 (2)	0.33190 (9)	0.0441 (5)
C9	0.1664 (4)	0.4088 (3)	0.27267 (10)	0.0536 (6)
C10	0.3383 (5)	0.3483 (3)	0.24667 (12)	0.0701 (8)
H10	0.3632	0.3679	0.2077	0.084*
C11	0.4762 (5)	0.2585 (3)	0.27715 (13)	0.0757 (9)
H11	0.5909	0.2167	0.2583	0.091*
C12	0.4452 (4)	0.2308 (3)	0.33475 (11)	0.0566 (7)
H12	0.5395	0.1724	0.3557	0.068*
C13	−0.0598 (4)	0.4452 (3)	0.36156 (12)	0.0601 (7)
H13A	−0.0457	0.5528	0.3637	0.072*
H13B	−0.0697	0.4045	0.4000	0.072*
H13C	−0.1837	0.4203	0.3402	0.072*
C14	0.0210 (6)	0.5071 (4)	0.23845 (14)	0.0840 (10)
H14A	0.0214	0.6070	0.2544	0.101*
H14B	−0.1179	0.4664	0.2402	0.101*
H14C	0.0665	0.5108	0.1988	0.101*
N1	0.2351 (3)	0.2670 (2)	0.42314 (7)	0.0413 (5)
H1N	0.337 (4)	0.290 (3)	0.4439 (10)	0.050*
O1	−0.0648 (3)	0.09633 (19)	0.41129 (7)	0.0567 (5)
O2	0.0967 (3)	0.13781 (18)	0.50761 (6)	0.0577 (5)
S1	0.11619 (8)	0.11797 (6)	0.44610 (2)	0.04071 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0474 (12)	0.0325 (11)	0.0367 (11)	−0.0028 (9)	0.0072 (10)	0.0039 (9)
C2	0.0512 (14)	0.0446 (13)	0.0562 (15)	0.0015 (11)	−0.0003 (11)	0.0037 (11)
C3	0.0525 (15)	0.0602 (15)	0.0826 (19)	0.0094 (13)	0.0059 (15)	0.0201 (14)
C4	0.074 (2)	0.0485 (16)	0.088 (2)	0.0167 (14)	0.0292 (17)	0.0089 (14)
C5	0.103 (3)	0.0439 (14)	0.0747 (19)	−0.0003 (17)	0.0165 (19)	−0.0139 (13)
C6	0.0650 (16)	0.0453 (14)	0.0588 (15)	−0.0036 (13)	0.0013 (12)	−0.0065 (11)
C7	0.0453 (13)	0.0366 (12)	0.0437 (12)	−0.0046 (10)	−0.0013 (10)	0.0016 (9)
C8	0.0463 (11)	0.0389 (11)	0.0471 (11)	−0.0040 (12)	−0.0060 (10)	−0.0038 (10)
C9	0.0728 (18)	0.0463 (13)	0.0418 (12)	−0.0153 (12)	−0.0039 (12)	0.0044 (10)
C10	0.095 (2)	0.0610 (17)	0.0545 (15)	−0.0060 (16)	0.0127 (16)	0.0077 (13)
C11	0.0747 (19)	0.0694 (19)	0.083 (2)	0.0123 (16)	0.0330 (17)	0.0058 (16)
C12	0.0488 (15)	0.0536 (15)	0.0674 (17)	0.0070 (12)	0.0105 (12)	0.0128 (12)
C13	0.0515 (16)	0.0658 (16)	0.0631 (16)	0.0125 (13)	0.0018 (12)	0.0035 (13)
C14	0.089 (2)	0.094 (2)	0.069 (2)	−0.002 (2)	−0.0176 (18)	0.0251 (17)
N1	0.0473 (11)	0.0380 (10)	0.0384 (10)	−0.0017 (9)	−0.0094 (9)	−0.0001 (8)
O1	0.0425 (10)	0.0555 (11)	0.0721 (11)	−0.0045 (8)	−0.0070 (7)	0.0018 (8)
O2	0.0708 (11)	0.0589 (10)	0.0432 (8)	0.0133 (10)	0.0158 (8)	0.0008 (7)
S1	0.0425 (3)	0.0397 (3)	0.0399 (3)	0.0026 (3)	0.0038 (2)	0.0009 (2)

C1—C6	1.371 (3)	C9—C10	1.363 (4)
C1—C2	1.388 (3)	C9—C14	1.500 (4)
C1—S1	1.762 (2)	C10—C11	1.381 (4)
C2—C3	1.379 (4)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.367 (4)
C3—C4	1.360 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.381 (5)	C13—H13A	0.9600
C4—H4	0.9300	C13—H13B	0.9600
C5—C6	1.380 (4)	C13—H13C	0.9600
C5—H5	0.9300	C14—H14A	0.9600
C6—H6	0.9300	C14—H14B	0.9600
C7—C8	1.385 (3)	C14—H14C	0.9600
C7—C12	1.401 (3)	N1—S1	1.615 (2)
C7—N1	1.453 (3)	N1—H1N	0.84 (3)
C8—C9	1.414 (3)	O1—S1	1.4221 (17)
C8—C13	1.485 (3)	O2—S1	1.4362 (15)
C6—C1—C2	120.6 (2)	C11—C10—H10	119.4
C6—C1—S1	120.57 (19)	C12—C11—C10	120.4 (3)
C2—C1—S1	118.80 (16)	C12—C11—H11	119.8
C3—C2—C1	119.2 (2)	C10—C11—H11	119.8
C3—C2—H2	120.4	C11—C12—C7	118.6 (3)
C1—C2—H2	120.4	C11—C12—H12	120.7
C4—C3—C2	120.4 (3)	C7—C12—H12	120.7
C4—C3—H3	119.8	C8—C13—H13A	109.5
C2—C3—H3	119.8	C8—C13—H13B	109.5
C3—C4—C5	120.2 (3)	H13A—C13—H13B	109.5
C3—C4—H4	119.9	C8—C13—H13C	109.5
C5—C4—H4	119.9	H13A—C13—H13C	109.5
C6—C5—C4	120.1 (3)	H13B—C13—H13C	109.5
C6—C5—H5	119.9	C9—C14—H14A	109.5
C4—C5—H5	119.9	C9—C14—H14B	109.5
C1—C6—C5	119.4 (3)	H14A—C14—H14B	109.5
C1—C6—H6	120.3	C9—C14—H14C	109.5
C5—C6—H6	120.3	H14A—C14—H14C	109.5
C8—C7—C12	122.2 (2)	H14B—C14—H14C	109.5
C8—C7—N1	118.4 (2)	C7—N1—S1	121.07 (14)
C12—C7—N1	119.4 (2)	C7—N1—H1N	114.0 (17)
C7—C8—C9	117.3 (2)	S1—N1—H1N	112.4 (17)
C7—C8—C13	121.1 (2)	O1—S1—O2	120.28 (11)
C9—C8—C13	121.6 (2)	O1—S1—N1	107.97 (10)
C10—C9—C8	120.3 (2)	O2—S1—N1	105.37 (10)
C10—C9—C14	119.8 (2)	O1—S1—C1	107.82 (10)
C8—C9—C14	119.9 (2)	O2—S1—C1	106.68 (10)
C9—C10—C11	121.2 (3)	N1—S1—C1	108.24 (9)
C9—C10—H10	119.4
C6—C1—C2—C3	−1.7 (3)	C14—C9—C10—C11	179.4 (3)
S1—C1—C2—C3	177.83 (19)	C9—C10—C11—C12	−1.4 (5)
C1—C2—C3—C4	1.1 (4)	C10—C11—C12—C7	1.6 (4)
C2—C3—C4—C5	1.0 (4)	C8—C7—C12—C11	−0.5 (4)
C3—C4—C5—C6	−2.5 (4)	N1—C7—C12—C11	−178.6 (2)
C2—C1—C6—C5	0.2 (4)	C8—C7—N1—S1	95.3 (2)
S1—C1—C6—C5	−179.3 (2)	C12—C7—N1—S1	−86.4 (2)
C4—C5—C6—C1	1.9 (4)	C7—N1—S1—O1	−45.5 (2)
C12—C7—C8—C9	−0.8 (3)	C7—N1—S1—O2	−175.20 (17)
N1—C7—C8—C9	177.31 (19)	C7—N1—S1—C1	70.97 (19)
C12—C7—C8—C13	−179.5 (2)	C6—C1—S1—O1	−1.1 (2)
N1—C7—C8—C13	−1.4 (3)	C2—C1—S1—O1	179.35 (17)
C7—C8—C9—C10	1.1 (3)	C6—C1—S1—O2	129.3 (2)
C13—C8—C9—C10	179.7 (2)	C2—C1—S1—O2	−50.2 (2)
C7—C8—C9—C14	−178.3 (2)	C6—C1—S1—N1	−117.7 (2)
C13—C8—C9—C14	0.3 (3)	C2—C1—S1—N1	62.79 (19)
C8—C9—C10—C11	0.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.84 (3)	2.10 (3)	2.936 (2)	176 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.84 (3)	2.10 (3)	2.936 (2)	176 (2)

Symmetry code: (i) .