N-(2,6-Dimethyl-phen-yl)benzene-sulfonamide.

In the crystal structure of the title compound, C(14)H(15)NO(2)S, the N-H bond is trans to one of the S=O double bonds, similar to what is observed in N-(2-methyl-phen-yl)benzene-sulfonamide and other aryl sulfonamides. The two aromatic rings enclose a dihedral angle of 44.9 (1)°. The mol-ecules are connected by inter-molecular N-H⋯O hydrogen bonds into chains running along the a axis. An intermolecular C-H⋯O hydrogen bond is also present.

Related literature

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

Experimental

Crystal data

C14H15NO2S

M = 261.33

Monoclinic,

a = 5.2133 (7) Å

b = 17.971 (2) Å

c = 14.040 (1) Å

β = 91.681 (9)°

V = 1314.8 (2) Å3

Z = 4

Cu Kα radiation

μ = 2.13 mm−1

T = 299 (2) K

0.55 × 0.35 × 0.33 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

2622 measured reflections

2340 independent reflections

2197 reflections with I > 2σ(I)

R int = 0.071

3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.134

S = 1.08

2340 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.41 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: 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, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808024653/bt2760sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024653/bt2760Isup2.hkl

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

C14H15NO2S	F000 = 552
Mr = 261.33	Dx = 1.320 Mg m−3
Monoclinic, P21/n	Cu Kα radiation λ = 1.54180 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 5.2133 (7) Å	θ = 4.0–19.2º
b = 17.971 (2) Å	µ = 2.14 mm−1
c = 14.040 (1) Å	T = 299 (2) K
β = 91.681 (9)º	Prism, colourless
V = 1314.8 (2) Å3	0.55 × 0.35 × 0.33 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.071
Radiation source: fine-focus sealed tube	θmax = 66.9º
Monochromator: graphite	θmin = 4.0º
T = 299(2) K	h = −6→1
ω/2θ scans	k = −21→0
Absorption correction: none	l = −16→16
2622 measured reflections	3 standard reflections
2340 independent reflections	every 120 min
2197 reflections with I > 2σ(I)	intensity decay: 1.0%

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.047	w = 1/[σ2(Fo2) + (0.0807P)2 + 0.6081P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.134	(Δ/σ)max = 0.001
S = 1.08	Δρmax = 0.35 e Å−3
2340 reflections	Δρmin = −0.41 e Å−3
164 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0060 (9)
Secondary atom site location: difference Fourier map

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	−0.0070 (4)	0.19125 (11)	0.78195 (15)	0.0359 (5)
C2	−0.2175 (4)	0.23812 (13)	0.7860 (2)	0.0518 (6)
H2	−0.3303	0.2434	0.7339	0.062*
C3	−0.2557 (5)	0.27695 (15)	0.8699 (3)	0.0677 (8)
H3	−0.3972	0.3081	0.8744	0.081*
C4	−0.0875 (6)	0.26990 (16)	0.9461 (2)	0.0666 (8)
H4	−0.1141	0.2969	1.0014	0.080*
C5	0.1186 (6)	0.22354 (15)	0.94146 (19)	0.0590 (7)
H5	0.2309	0.2186	0.9938	0.071*
C6	0.1608 (4)	0.18376 (13)	0.85885 (17)	0.0453 (5)
H6	0.3017	0.1522	0.8554	0.054*
C7	−0.0178 (4)	0.00007 (11)	0.74093 (15)	0.0373 (5)
C8	−0.1139 (4)	−0.01229 (12)	0.83144 (16)	0.0437 (5)
C9	−0.0176 (6)	−0.07186 (15)	0.8839 (2)	0.0609 (7)
H9	−0.0788	−0.0809	0.9444	0.073*
C10	0.1675 (7)	−0.11784 (16)	0.8480 (3)	0.0730 (9)
H10	0.2336	−0.1568	0.8848	0.088*
C11	0.2541 (6)	−0.10620 (14)	0.7582 (2)	0.0680 (8)
H11	0.3769	−0.1382	0.7343	0.082*
C12	0.1628 (5)	−0.04751 (13)	0.70148 (18)	0.0498 (6)
C13	−0.3213 (5)	0.03545 (14)	0.87194 (18)	0.0521 (6)
H13A	−0.4740	0.0316	0.8323	0.063*
H13B	−0.2651	0.0863	0.8741	0.063*
H13C	−0.3570	0.0189	0.9352	0.063*
C14	0.2511 (6)	−0.03980 (16)	0.6006 (2)	0.0683 (8)
H14A	0.2690	0.0120	0.5853	0.082*
H14B	0.1270	−0.0622	0.5576	0.082*
H14C	0.4135	−0.0643	0.5947	0.082*
N1	−0.1132 (3)	0.06164 (9)	0.68444 (12)	0.0371 (4)
H1N	−0.2573	0.0571	0.6536	0.044*
O1	0.3127 (3)	0.12146 (10)	0.67758 (12)	0.0478 (4)
O2	−0.0692 (4)	0.17882 (10)	0.59926 (12)	0.0576 (5)
S1	0.04474 (9)	0.13941 (3)	0.67748 (3)	0.0358 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0330 (10)	0.0277 (9)	0.0476 (11)	−0.0044 (7)	0.0082 (8)	0.0010 (8)
C2	0.0383 (11)	0.0382 (12)	0.0794 (17)	0.0005 (9)	0.0079 (11)	−0.0024 (11)
C3	0.0519 (14)	0.0440 (14)	0.109 (2)	0.0011 (11)	0.0324 (16)	−0.0178 (14)
C4	0.0731 (18)	0.0538 (15)	0.0749 (19)	−0.0173 (14)	0.0336 (15)	−0.0237 (14)
C5	0.0697 (16)	0.0576 (15)	0.0500 (14)	−0.0172 (13)	0.0086 (12)	−0.0106 (12)
C6	0.0437 (11)	0.0425 (12)	0.0500 (12)	−0.0010 (9)	0.0044 (9)	−0.0046 (9)
C7	0.0377 (10)	0.0300 (10)	0.0437 (11)	−0.0023 (8)	−0.0068 (8)	−0.0014 (8)
C8	0.0421 (11)	0.0398 (11)	0.0490 (12)	−0.0076 (9)	−0.0027 (9)	0.0031 (9)
C9	0.0698 (17)	0.0511 (14)	0.0614 (16)	−0.0060 (12)	−0.0037 (12)	0.0180 (12)
C10	0.088 (2)	0.0455 (14)	0.085 (2)	0.0092 (14)	−0.0165 (17)	0.0183 (14)
C11	0.0701 (18)	0.0419 (14)	0.091 (2)	0.0179 (13)	−0.0075 (15)	−0.0061 (14)
C12	0.0523 (13)	0.0388 (12)	0.0579 (14)	0.0040 (10)	−0.0045 (10)	−0.0108 (10)
C13	0.0489 (13)	0.0557 (14)	0.0523 (13)	−0.0057 (11)	0.0106 (10)	0.0054 (11)
C14	0.0828 (19)	0.0587 (16)	0.0638 (17)	0.0143 (14)	0.0110 (14)	−0.0211 (13)
N1	0.0333 (8)	0.0372 (9)	0.0402 (9)	−0.0016 (7)	−0.0069 (7)	0.0004 (7)
O1	0.0331 (8)	0.0539 (9)	0.0569 (10)	−0.0006 (7)	0.0104 (7)	−0.0048 (7)
O2	0.0690 (11)	0.0563 (10)	0.0473 (9)	0.0011 (8)	−0.0016 (8)	0.0193 (8)
S1	0.0351 (3)	0.0364 (3)	0.0361 (3)	−0.00027 (18)	0.0040 (2)	0.00487 (18)

C1—C6	1.376 (3)	C9—C10	1.377 (5)
C1—C2	1.386 (3)	C9—H9	0.9300
C1—S1	1.765 (2)	C10—C11	1.368 (5)
C2—C3	1.388 (4)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.397 (4)
C3—C4	1.369 (5)	C11—H11	0.9300
C3—H3	0.9300	C12—C14	1.508 (4)
C4—C5	1.363 (4)	C13—H13A	0.9600
C4—H4	0.9300	C13—H13B	0.9600
C5—C6	1.386 (3)	C13—H13C	0.9600
C5—H5	0.9300	C14—H14A	0.9600
C6—H6	0.9300	C14—H14B	0.9600
C7—C8	1.397 (3)	C14—H14C	0.9600
C7—C12	1.398 (3)	N1—S1	1.6263 (17)
C7—N1	1.441 (3)	N1—H1N	0.8600
C8—C9	1.386 (3)	O1—S1	1.4334 (16)
C8—C13	1.505 (3)	O2—S1	1.4221 (17)
C6—C1—C2	120.9 (2)	C9—C10—H10	120.0
C6—C1—S1	119.41 (16)	C10—C11—C12	121.7 (3)
C2—C1—S1	119.71 (18)	C10—C11—H11	119.2
C1—C2—C3	118.3 (3)	C12—C11—H11	119.2
C1—C2—H2	120.8	C11—C12—C7	117.3 (3)
C3—C2—H2	120.8	C11—C12—C14	119.8 (2)
C4—C3—C2	120.8 (2)	C7—C12—C14	122.9 (2)
C4—C3—H3	119.6	C8—C13—H13A	109.5
C2—C3—H3	119.6	C8—C13—H13B	109.5
C5—C4—C3	120.5 (3)	H13A—C13—H13B	109.5
C5—C4—H4	119.8	C8—C13—H13C	109.5
C3—C4—H4	119.8	H13A—C13—H13C	109.5
C4—C5—C6	120.0 (3)	H13B—C13—H13C	109.5
C4—C5—H5	120.0	C12—C14—H14A	109.5
C6—C5—H5	120.0	C12—C14—H14B	109.5
C1—C6—C5	119.5 (2)	H14A—C14—H14B	109.5
C1—C6—H6	120.2	C12—C14—H14C	109.5
C5—C6—H6	120.2	H14A—C14—H14C	109.5
C8—C7—C12	121.8 (2)	H14B—C14—H14C	109.5
C8—C7—N1	119.69 (19)	C7—N1—S1	121.72 (13)
C12—C7—N1	118.5 (2)	C7—N1—H1N	119.1
C9—C8—C7	118.2 (2)	S1—N1—H1N	119.1
C9—C8—C13	119.5 (2)	O2—S1—O1	119.85 (11)
C7—C8—C13	122.3 (2)	O2—S1—N1	105.89 (10)
C10—C9—C8	121.0 (3)	O1—S1—N1	107.55 (10)
C10—C9—H9	119.5	O2—S1—C1	107.95 (11)
C8—C9—H9	119.5	O1—S1—C1	106.89 (10)
C11—C10—C9	120.0 (3)	N1—S1—C1	108.28 (9)
C11—C10—H10	120.0
C6—C1—C2—C3	−0.4 (3)	C10—C11—C12—C14	−176.0 (3)
S1—C1—C2—C3	178.70 (18)	C8—C7—C12—C11	−3.2 (3)
C1—C2—C3—C4	0.9 (4)	N1—C7—C12—C11	179.3 (2)
C2—C3—C4—C5	−1.1 (4)	C8—C7—C12—C14	174.0 (2)
C3—C4—C5—C6	0.7 (4)	N1—C7—C12—C14	−3.5 (3)
C2—C1—C6—C5	0.1 (3)	C8—C7—N1—S1	99.9 (2)
S1—C1—C6—C5	−179.04 (18)	C12—C7—N1—S1	−82.5 (2)
C4—C5—C6—C1	−0.2 (4)	C7—N1—S1—O2	165.74 (17)
C12—C7—C8—C9	2.6 (3)	C7—N1—S1—O1	36.48 (19)
N1—C7—C8—C9	−179.8 (2)	C7—N1—S1—C1	−78.70 (18)
C12—C7—C8—C13	−175.8 (2)	C6—C1—S1—O2	−153.98 (17)
N1—C7—C8—C13	1.8 (3)	C2—C1—S1—O2	26.9 (2)
C7—C8—C9—C10	−0.1 (4)	C6—C1—S1—O1	−23.8 (2)
C13—C8—C9—C10	178.3 (3)	C2—C1—S1—O1	157.06 (17)
C8—C9—C10—C11	−1.7 (5)	C6—C1—S1—N1	91.81 (18)
C9—C10—C11—C12	1.2 (5)	C2—C1—S1—N1	−87.33 (18)
C10—C11—C12—C7	1.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86	2.55	3.179 (2)	131
C5—H5···O2ii	0.93	2.57	3.229 (3)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86	2.55	3.179 (2)	131
C5—H5⋯O2ii	0.93	2.57	3.229 (3)	129

Symmetry codes: (i) ; (ii) .