N-(4-Methyl-benzo-yl)benzene-sulfonamide.

In the title compound, C(14)H(13)NO(3)S, the conformation of the N-H bond in the C-SO(2)-NH-C(O) segment is anti to the C=O bond. The dihedral angle between the sulfonyl benzene ring and the S-N-C-O segment (r.m.s. deviation = 0.039 Å) is 77.1 (1)° and that between the sulfonyl and benzoyl benzene rings is 71.9 (1)°.

Related literature

For background to our study of the effect of ring and side-chain substituents on the crystal structures of N-aromatic sulfonamides and for related structures, see: Gowda et al. (2009 ▶); n class="Chemical">Suchetan et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C14H13NO3S

M = 275.31

Triclinic,

a = 5.5519 (6) Å

b = 10.541 (1) Å

c = 11.105 (1) Å

α = 85.654 (9)°

β = 83.667 (9)°

γ = 81.949 (9)°

V = 638.36 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 299 K

0.40 × 0.32 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.904, T max = 0.960

4293 measured reflections

2595 independent reflections

2207 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.109

S = 1.08

2595 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data n class="Disease">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/S1600536810023974/ci5108sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023974/ci5108Isup2.hkl

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

C14H13NO3S	Z = 2
Mr = 275.31	F(000) = 288
Triclinic, P1	Dx = 1.432 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.5519 (6) Å	Cell parameters from 2679 reflections
b = 10.541 (1) Å	θ = 2.6–27.7°
c = 11.105 (1) Å	µ = 0.26 mm−1
α = 85.654 (9)°	T = 299 K
β = 83.667 (9)°	Needle, colourless
γ = 81.949 (9)°	0.40 × 0.32 × 0.16 mm
V = 638.36 (11) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2595 independent reflections
Radiation source: fine-focus sealed tube	2207 reflections with I > 2σ(I)
graphite	Rint = 0.017
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −6→6
Tmin = 0.904, Tmax = 0.960	k = −13→11
4293 measured reflections	l = −13→12

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0564P)2 + 0.1768P] where P = (Fo2 + 2Fc2)/3
2595 reflections	(Δ/σ)max = 0.020
173 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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	0.0535 (3)	0.17087 (15)	0.37945 (14)	0.0370 (3)
C2	0.2512 (3)	0.07861 (18)	0.39763 (17)	0.0491 (4)
H2	0.3709	0.0944	0.4448	0.059*
C3	0.2687 (4)	−0.03734 (19)	0.34486 (19)	0.0557 (5)
H3	0.4008	−0.1001	0.3567	0.067*
C4	0.0919 (4)	−0.06031 (17)	0.27507 (18)	0.0514 (5)
H4	0.1050	−0.1383	0.2394	0.062*
C5	−0.1047 (4)	0.03194 (19)	0.25778 (17)	0.0517 (5)
H5	−0.2241	0.0157	0.2106	0.062*
C6	−0.1262 (3)	0.14869 (17)	0.31001 (16)	0.0439 (4)
H6	−0.2592	0.2110	0.2985	0.053*
C7	0.1508 (3)	0.45512 (14)	0.24545 (14)	0.0362 (3)
C8	0.2982 (3)	0.55415 (14)	0.18611 (13)	0.0345 (3)
C9	0.4790 (3)	0.60283 (16)	0.23892 (15)	0.0393 (4)
H9	0.5113	0.5748	0.3177	0.047*
C10	0.6111 (3)	0.69266 (17)	0.17506 (15)	0.0429 (4)
H10	0.7328	0.7235	0.2113	0.051*
C11	0.5653 (3)	0.73765 (16)	0.05771 (15)	0.0403 (4)
C12	0.3825 (3)	0.69012 (18)	0.00681 (16)	0.0471 (4)
H12	0.3477	0.7197	−0.0712	0.056*
C13	0.2508 (3)	0.60001 (17)	0.06897 (15)	0.0451 (4)
H13	0.1291	0.5695	0.0324	0.054*
C14	0.7134 (4)	0.83301 (19)	−0.01353 (19)	0.0553 (5)
H14A	0.8409	0.7882	−0.0661	0.066*
H14B	0.7844	0.8795	0.0415	0.066*
H14C	0.6090	0.8920	−0.0613	0.066*
N1	0.2026 (3)	0.40757 (13)	0.36175 (13)	0.0466 (4)
H1N	0.3319	0.4262	0.3887	0.056*
O1	0.1439 (3)	0.29602 (14)	0.55935 (12)	0.0705 (5)
O2	−0.2229 (3)	0.37520 (13)	0.45410 (13)	0.0618 (4)
O3	−0.0051 (2)	0.41356 (12)	0.19791 (11)	0.0493 (3)
S1	0.02709 (9)	0.31703 (4)	0.45017 (4)	0.04709 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0466 (9)	0.0344 (8)	0.0314 (8)	−0.0135 (7)	−0.0018 (6)	0.0008 (6)
C2	0.0481 (10)	0.0518 (10)	0.0501 (10)	−0.0113 (8)	−0.0125 (8)	−0.0001 (8)
C3	0.0556 (11)	0.0452 (10)	0.0633 (12)	−0.0003 (8)	−0.0039 (9)	0.0008 (9)
C4	0.0641 (12)	0.0386 (9)	0.0524 (11)	−0.0164 (8)	0.0059 (9)	−0.0079 (8)
C5	0.0555 (11)	0.0545 (11)	0.0510 (11)	−0.0219 (9)	−0.0081 (8)	−0.0105 (8)
C6	0.0453 (9)	0.0427 (9)	0.0453 (9)	−0.0096 (7)	−0.0076 (7)	−0.0014 (7)
C7	0.0448 (9)	0.0310 (8)	0.0330 (8)	−0.0035 (6)	−0.0065 (6)	−0.0027 (6)
C8	0.0391 (8)	0.0319 (8)	0.0313 (8)	−0.0004 (6)	−0.0035 (6)	−0.0018 (6)
C9	0.0429 (9)	0.0439 (9)	0.0313 (8)	−0.0054 (7)	−0.0071 (6)	0.0016 (6)
C10	0.0417 (9)	0.0476 (9)	0.0408 (9)	−0.0092 (7)	−0.0061 (7)	−0.0030 (7)
C11	0.0419 (9)	0.0359 (8)	0.0397 (8)	0.0000 (7)	0.0026 (7)	−0.0005 (6)
C12	0.0571 (11)	0.0495 (10)	0.0342 (8)	−0.0070 (8)	−0.0097 (7)	0.0074 (7)
C13	0.0524 (10)	0.0494 (10)	0.0366 (9)	−0.0127 (8)	−0.0145 (7)	0.0030 (7)
C14	0.0585 (12)	0.0500 (11)	0.0552 (11)	−0.0114 (9)	0.0036 (9)	0.0053 (9)
N1	0.0680 (10)	0.0420 (8)	0.0359 (7)	−0.0246 (7)	−0.0154 (7)	0.0053 (6)
O1	0.1269 (14)	0.0621 (9)	0.0333 (7)	−0.0439 (9)	−0.0218 (7)	0.0059 (6)
O2	0.0745 (10)	0.0493 (8)	0.0565 (8)	−0.0036 (7)	0.0148 (7)	−0.0111 (6)
O3	0.0544 (7)	0.0519 (7)	0.0459 (7)	−0.0172 (6)	−0.0166 (6)	0.0056 (5)
S1	0.0756 (3)	0.0393 (2)	0.0295 (2)	−0.0204 (2)	−0.00330 (19)	−0.00178 (16)

C1—C6	1.381 (2)	C9—C10	1.384 (2)
C1—C2	1.382 (3)	C9—H9	0.93
C1—S1	1.7626 (16)	C10—C11	1.391 (2)
C2—C3	1.382 (3)	C10—H10	0.93
C2—H2	0.93	C11—C12	1.383 (2)
C3—C4	1.373 (3)	C11—C14	1.510 (2)
C3—H3	0.93	C12—C13	1.377 (2)
C4—C5	1.376 (3)	C12—H12	0.93
C4—H4	0.93	C13—H13	0.93
C5—C6	1.385 (3)	C14—H14A	0.96
C5—H5	0.93	C14—H14B	0.96
C6—H6	0.93	C14—H14C	0.96
C7—O3	1.209 (2)	N1—S1	1.6529 (15)
C7—N1	1.395 (2)	N1—H1N	0.86
C7—C8	1.487 (2)	O1—S1	1.4257 (14)
C8—C9	1.391 (2)	O2—S1	1.4340 (15)
C8—C13	1.393 (2)
C6—C1—C2	121.09 (16)	C9—C10—C11	121.20 (16)
C6—C1—S1	119.75 (13)	C9—C10—H10	119.4
C2—C1—S1	119.13 (13)	C11—C10—H10	119.4
C3—C2—C1	119.19 (17)	C12—C11—C10	117.86 (15)
C3—C2—H2	120.4	C12—C11—C14	120.74 (16)
C1—C2—H2	120.4	C10—C11—C14	121.39 (16)
C4—C3—C2	120.29 (18)	C13—C12—C11	121.56 (16)
C4—C3—H3	119.9	C13—C12—H12	119.2
C2—C3—H3	119.9	C11—C12—H12	119.2
C3—C4—C5	120.12 (17)	C12—C13—C8	120.55 (16)
C3—C4—H4	119.9	C12—C13—H13	119.7
C5—C4—H4	119.9	C8—C13—H13	119.7
C4—C5—C6	120.56 (17)	C11—C14—H14A	109.5
C4—C5—H5	119.7	C11—C14—H14B	109.5
C6—C5—H5	119.7	H14A—C14—H14B	109.5
C1—C6—C5	118.75 (17)	C11—C14—H14C	109.5
C1—C6—H6	120.6	H14A—C14—H14C	109.5
C5—C6—H6	120.6	H14B—C14—H14C	109.5
O3—C7—N1	119.51 (15)	C7—N1—S1	123.07 (12)
O3—C7—C8	123.77 (14)	C7—N1—H1N	118.5
N1—C7—C8	116.70 (14)	S1—N1—H1N	118.5
C9—C8—C13	118.37 (15)	O1—S1—O2	119.65 (10)
C9—C8—C7	124.69 (14)	O1—S1—N1	103.47 (8)
C13—C8—C7	116.93 (14)	O2—S1—N1	109.71 (8)
C10—C9—C8	120.45 (15)	O1—S1—C1	109.18 (9)
C10—C9—H9	119.8	O2—S1—C1	108.24 (8)
C8—C9—H9	119.8	N1—S1—C1	105.73 (8)
C6—C1—C2—C3	0.2 (3)	C10—C11—C12—C13	−0.7 (3)
S1—C1—C2—C3	178.30 (14)	C14—C11—C12—C13	177.89 (17)
C1—C2—C3—C4	0.1 (3)	C11—C12—C13—C8	0.2 (3)
C2—C3—C4—C5	−0.3 (3)	C9—C8—C13—C12	0.8 (3)
C3—C4—C5—C6	0.2 (3)	C7—C8—C13—C12	−178.80 (16)
C2—C1—C6—C5	−0.4 (3)	O3—C7—N1—S1	−12.2 (2)
S1—C1—C6—C5	−178.42 (13)	C8—C7—N1—S1	168.97 (11)
C4—C5—C6—C1	0.2 (3)	C7—N1—S1—O1	−177.83 (14)
O3—C7—C8—C9	−179.72 (16)	C7—N1—S1—O2	−49.07 (16)
N1—C7—C8—C9	−0.9 (2)	C7—N1—S1—C1	67.44 (15)
O3—C7—C8—C13	−0.1 (2)	C6—C1—S1—O1	149.92 (14)
N1—C7—C8—C13	178.70 (15)	C2—C1—S1—O1	−28.17 (17)
C13—C8—C9—C10	−1.3 (2)	C6—C1—S1—O2	18.16 (16)
C7—C8—C9—C10	178.29 (15)	C2—C1—S1—O2	−159.93 (14)
C8—C9—C10—C11	0.8 (3)	C6—C1—S1—N1	−99.34 (14)
C9—C10—C11—C12	0.2 (3)	C2—C1—S1—N1	82.58 (15)
C9—C10—C11—C14	−178.37 (16)