N,4-Dimethyl-N-phenyl­benzene­sulfonamide

The two rings in the title compound, C₁₄H₁₅NO₂S, are inclined to each other by an angle of 43.78 (13)°. In the crystal structure, mol­ecules are linked by a single weak inter­molecular C—H...O hydrogen bond involving an S=O group as acceptor.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.043
• wR factor = 0.121
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   O2      ..       6.34 su
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C9     -C14           1.37 Ang.

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          6

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

The N atom of the title sulfonamide, (I), has a pyramidal geometry (Fig. 1), but the pyramid is somewhat shallower than expected for pure sp³ hybridization [C9—N1—C8: 116.86 (18)°; C9—N1—S1: 117.00 (14)°; C8—N1—S1: 116.69 (15)°]. The benzene and phenyl rings are inclined to each other by an angle of 43.78 (13)°. A weak C—H···O hydrogen bond (Table 1) involving a S═O group of sulfonamide links molecules to form chains in the crystal structure. No significant π–π interactions are observed in the packing structure.

Related literature

For related N-arylbenzenesulfonamides, see: Shi (2007); Chang et al. (2007); Yu et al. (2007); Xing et al. (2006); Yu (2006); Xing & Zeng (2005).

S2. Experimental

The title compound was obtained by reaction of N-methylaniline with p-tosyl chloride in the presence of aqueous sodium biscarbonate. Colourless blocks of (I) were grown by slow evaporation of an ethyl acetate solution at 298 K.

S3. Refinement

Methyl C atom of the p-tolyl group was restrained with a standard deviation of 0.01 Ų so that U_ij components approximate to isotropic behaviour. All H atoms were positioned geometrically (C—H = 0.93 Å for aromatic CH, 0.96 Å for methyl CH₃) and refined as riding with U_iso(H) = 1.2U_eq(C) for aromatic CH and U_iso(H) = 1.2U_eq(C) for methyl CH₃.

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures

Fig. 1. The molecular structure of (I), with the atom-numbering scheme and 30% probability displacement ellipsoids for non-H atoms.

N,4-Dimethyl-N-phenylbenzenesulfonamide

Crystal data

C14H15NO2S	F(000) = 552
Mr = 261.33	Dx = 1.312 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2238 reflections
a = 14.156 (4) Å	θ = 2.7–25.0°
b = 6.2251 (17) Å	µ = 0.24 mm^−1
c = 16.295 (5) Å	T = 294 K
β = 112.821 (5)°	Block, colourless
V = 1323.5 (6) Å^3	0.22 × 0.20 × 0.14 mm
Z = 4

Data collection

Bruker SMART 1K CCD area-detector diffractometer	2341 independent reflections
Radiation source: fine-focus sealed tube	1738 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ϕ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −9→16
Tmin = 0.950, Tmax = 0.968	k = −7→7
6561 measured reflections	l = −19→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.121	w = 1/[σ^2(Fo^2) + (0.0591P)^2 + 0.4321P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
2341 reflections	Δρmax = 0.30 e Å^−3
165 parameters	Δρmin = −0.21 e Å^−3
6 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.046 (3)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.86815 (5)	0.54101 (10)	0.07849 (4)	0.0497 (2)
O1	0.83906 (15)	0.7595 (3)	0.06292 (12)	0.0671 (5)
O2	0.96603 (13)	0.4862 (3)	0.14363 (11)	0.0689 (6)
N1	0.86374 (13)	0.4405 (3)	−0.01530 (12)	0.0420 (5)
C1	0.77411 (17)	0.4082 (4)	0.10434 (14)	0.0454 (6)
C2	0.6781 (2)	0.4967 (4)	0.08104 (17)	0.0595 (7)
H2	0.6641	0.6325	0.0554	0.071*
C3	0.6033 (2)	0.3831 (5)	0.09588 (19)	0.0698 (8)
H3	0.5390	0.4449	0.0812	0.084*
C4	0.6209 (2)	0.1798 (5)	0.13204 (17)	0.0623 (7)
C5	0.7185 (2)	0.0976 (4)	0.15728 (18)	0.0623 (7)
H5	0.7331	−0.0366	0.1843	0.075*
C6	0.79442 (19)	0.2084 (4)	0.14360 (16)	0.0533 (6)
H6	0.8596	0.1491	0.1607	0.064*
C7	0.5362 (3)	0.0523 (6)	0.1427 (2)	0.0971 (11)
H7A	0.5218	0.1096	0.1912	0.146*
H7B	0.5570	−0.0951	0.1547	0.146*
H7C	0.4758	0.0608	0.0888	0.146*
C8	0.91396 (19)	0.2314 (4)	−0.01064 (18)	0.0573 (7)
H8A	0.8734	0.1205	0.0006	0.086*
H8B	0.9807	0.2338	0.0366	0.086*
H8C	0.9206	0.2035	−0.0661	0.086*
C9	0.77237 (16)	0.4813 (3)	−0.09328 (14)	0.0400 (5)
C10	0.69764 (18)	0.3281 (4)	−0.12578 (16)	0.0547 (7)
H10	0.7039	0.1977	−0.0963	0.066*
C11	0.6130 (2)	0.3688 (5)	−0.20252 (18)	0.0672 (8)
H11	0.5627	0.2640	−0.2253	0.081*
C12	0.6022 (2)	0.5600 (5)	−0.24519 (17)	0.0650 (7)
H12	0.5443	0.5871	−0.2963	0.078*
C13	0.6769 (2)	0.7121 (5)	−0.21258 (18)	0.0637 (7)
H13	0.6697	0.8432	−0.2418	0.076*
C14	0.76271 (19)	0.6736 (4)	−0.13699 (16)	0.0515 (6)
H14	0.8139	0.7771	−0.1156	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0567 (4)	0.0452 (4)	0.0430 (4)	−0.0123 (3)	0.0148 (3)	−0.0036 (3)
O1	0.1001 (14)	0.0396 (9)	0.0658 (12)	−0.0125 (9)	0.0367 (10)	−0.0088 (8)
O2	0.0501 (10)	0.0910 (14)	0.0489 (11)	−0.0176 (9)	0.0008 (8)	0.0022 (9)
N1	0.0419 (10)	0.0403 (10)	0.0425 (11)	−0.0045 (8)	0.0149 (8)	−0.0001 (8)
C1	0.0520 (14)	0.0445 (13)	0.0380 (12)	−0.0004 (10)	0.0155 (10)	−0.0003 (10)
C2	0.0616 (17)	0.0583 (16)	0.0557 (16)	0.0072 (12)	0.0195 (13)	0.0131 (12)
C3	0.0538 (17)	0.095 (2)	0.0619 (18)	0.0071 (15)	0.0239 (14)	0.0123 (16)
C4	0.0694 (18)	0.0772 (19)	0.0490 (15)	−0.0138 (15)	0.0325 (13)	−0.0015 (13)
C5	0.082 (2)	0.0521 (15)	0.0633 (17)	0.0013 (14)	0.0399 (15)	0.0081 (13)
C6	0.0588 (15)	0.0502 (14)	0.0550 (15)	0.0042 (11)	0.0266 (12)	0.0057 (11)
C7	0.090 (2)	0.122 (3)	0.098 (3)	−0.027 (2)	0.058 (2)	0.005 (2)
C8	0.0600 (16)	0.0511 (15)	0.0643 (17)	0.0055 (12)	0.0280 (13)	0.0010 (12)
C9	0.0427 (12)	0.0415 (12)	0.0385 (12)	−0.0046 (9)	0.0186 (10)	−0.0017 (9)
C10	0.0569 (15)	0.0532 (15)	0.0498 (15)	−0.0142 (12)	0.0162 (12)	0.0030 (12)
C11	0.0539 (16)	0.083 (2)	0.0584 (17)	−0.0234 (14)	0.0150 (13)	−0.0073 (15)
C12	0.0531 (16)	0.090 (2)	0.0455 (15)	0.0020 (15)	0.0118 (12)	0.0092 (15)
C13	0.0734 (18)	0.0612 (17)	0.0567 (17)	0.0089 (14)	0.0253 (14)	0.0161 (13)
C14	0.0584 (15)	0.0447 (14)	0.0511 (15)	−0.0059 (11)	0.0210 (12)	0.0029 (11)

Geometric parameters (Å, º)

S1—O1	1.4152 (18)	C7—H7A	0.9600
S1—O2	1.4219 (18)	C7—H7B	0.9600
S1—N1	1.6300 (19)	C7—H7C	0.9600
S1—C1	1.751 (2)	C8—H8A	0.9600
N1—C9	1.441 (3)	C8—H8B	0.9600
N1—C8	1.471 (3)	C8—H8C	0.9600
C1—C2	1.376 (3)	C9—C10	1.369 (3)
C1—C6	1.377 (3)	C9—C14	1.372 (3)
C2—C3	1.370 (4)	C10—C11	1.379 (3)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.378 (4)	C11—C12	1.357 (4)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.378 (4)	C12—C13	1.365 (4)
C4—C7	1.503 (4)	C12—H12	0.9300
C5—C6	1.365 (4)	C13—C14	1.375 (3)
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—H14	0.9300
O1—S1—O2	119.73 (11)	H7A—C7—H7B	109.5
O1—S1—N1	107.34 (10)	C4—C7—H7C	109.5
O2—S1—N1	106.24 (11)	H7A—C7—H7C	109.5
O1—S1—C1	107.52 (12)	H7B—C7—H7C	109.5
O2—S1—C1	108.60 (11)	N1—C8—H8A	109.5
N1—S1—C1	106.75 (10)	N1—C8—H8B	109.5
C9—N1—C8	116.86 (18)	H8A—C8—H8B	109.5
C9—N1—S1	117.00 (14)	N1—C8—H8C	109.5
C8—N1—S1	116.69 (15)	H8A—C8—H8C	109.5
C2—C1—C6	119.7 (2)	H8B—C8—H8C	109.5
C2—C1—S1	120.42 (19)	C10—C9—C14	120.0 (2)
C6—C1—S1	119.78 (18)	C10—C9—N1	120.9 (2)
C3—C2—C1	119.5 (2)	C14—C9—N1	119.07 (19)
C3—C2—H2	120.2	C9—C10—C11	119.5 (2)
C1—C2—H2	120.2	C9—C10—H10	120.2
C2—C3—C4	121.7 (3)	C11—C10—H10	120.2
C2—C3—H3	119.1	C12—C11—C10	120.7 (2)
C4—C3—H3	119.1	C12—C11—H11	119.6
C3—C4—C5	117.5 (2)	C10—C11—H11	119.6
C3—C4—C7	121.0 (3)	C11—C12—C13	119.6 (2)
C5—C4—C7	121.5 (3)	C11—C12—H12	120.2
C6—C5—C4	121.7 (3)	C13—C12—H12	120.2
C6—C5—H5	119.2	C12—C13—C14	120.6 (2)
C4—C5—H5	119.2	C12—C13—H13	119.7
C5—C6—C1	119.7 (2)	C14—C13—H13	119.7
C5—C6—H6	120.1	C9—C14—C13	119.5 (2)
C1—C6—H6	120.1	C9—C14—H14	120.2
C4—C7—H7A	109.5	C13—C14—H14	120.2
C4—C7—H7B	109.5
O1—S1—N1—C9	−48.66 (18)	C3—C4—C5—C6	−2.9 (4)
O2—S1—N1—C9	−177.86 (15)	C7—C4—C5—C6	176.6 (3)
C1—S1—N1—C9	66.39 (17)	C4—C5—C6—C1	0.6 (4)
O1—S1—N1—C8	165.89 (16)	C2—C1—C6—C5	1.4 (4)
O2—S1—N1—C8	36.69 (19)	S1—C1—C6—C5	−174.82 (19)
C1—S1—N1—C8	−79.07 (18)	C8—N1—C9—C10	44.9 (3)
O1—S1—C1—C2	19.8 (2)	S1—N1—C9—C10	−100.5 (2)
O2—S1—C1—C2	150.7 (2)	C8—N1—C9—C14	−132.6 (2)
N1—S1—C1—C2	−95.2 (2)	S1—N1—C9—C14	82.0 (2)
O1—S1—C1—C6	−164.01 (19)	C14—C9—C10—C11	0.0 (4)
O2—S1—C1—C6	−33.1 (2)	N1—C9—C10—C11	−177.5 (2)
N1—S1—C1—C6	81.1 (2)	C9—C10—C11—C12	−1.1 (4)
C6—C1—C2—C3	−1.1 (4)	C10—C11—C12—C13	1.1 (4)
S1—C1—C2—C3	175.2 (2)	C11—C12—C13—C14	−0.1 (4)
C1—C2—C3—C4	−1.4 (4)	C10—C9—C14—C13	1.0 (4)
C2—C3—C4—C5	3.3 (4)	N1—C9—C14—C13	178.5 (2)
C2—C3—C4—C7	−176.2 (3)	C12—C13—C14—C9	−1.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2^i	0.93	2.57	3.384 (4)	147

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.