N-Benzoyl-4-methyl-benzene-sulfonamide.

In the title compound, C(14)H(13)NO(3)S, the N-H bond in is anti to the C=O bond. The dihedral angle between the two aromatic rings is 79.4 (1)°. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, generating C(4) chains.

Related literature

For related structures, see: Gowda et al. (2009 ▶); Suchetan et al. (2010 ▶).

Experimental

Crystal data

C14H13NO3S

M = 275.31

Orthorhombic,

a = 5.1723 (5) Å

b = 14.785 (1) Å

c = 17.431 (1) Å

V = 1332.99 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 299 K

0.40 × 0.20 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.908, T max = 0.966

5515 measured reflections

2644 independent reflections

2388 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.084

S = 1.12

2644 reflections

176 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 1025 Friedel pairs

Flack parameter: 0.18 (8)

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED 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/S1600536810011967/bt5236sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011967/bt5236Isup2.hkl

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

C14H13NO3S	F(000) = 576
Mr = 275.31	Dx = 1.372 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3284 reflections
a = 5.1723 (5) Å	θ = 2.7–27.9°
b = 14.785 (1) Å	µ = 0.25 mm−1
c = 17.431 (1) Å	T = 299 K
V = 1332.99 (17) Å3	Thick needle, colourless
Z = 4	0.40 × 0.20 × 0.14 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2644 independent reflections
Radiation source: fine-focus sealed tube	2388 reflections with I > 2σ(I)
graphite	Rint = 0.013
Rotation method data acquisition using ω and phi scans.	θmax = 26.4°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −3→6
Tmin = 0.908, Tmax = 0.966	k = −18→14
5515 measured reflections	l = −21→19

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)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.084	w = 1/[σ2(Fo2) + (0.0398P)2 + 0.2729P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max = 0.009
2644 reflections	Δρmax = 0.16 e Å−3
176 parameters	Δρmin = −0.21 e Å−3
1 restraint	Absolute structure: Flack (1983), 1025 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.18 (8)

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.4594 (4)	0.46253 (13)	0.51327 (11)	0.0386 (4)
C2	0.5259 (5)	0.54024 (14)	0.55288 (13)	0.0515 (5)
H2	0.4556	0.5520	0.6010	0.062*
C3	0.6980 (5)	0.59989 (14)	0.52001 (14)	0.0594 (7)
H3	0.7444	0.6518	0.5468	0.071*
C4	0.8039 (4)	0.58456 (16)	0.44803 (14)	0.0538 (6)
C5	0.7308 (6)	0.50747 (16)	0.40883 (15)	0.0622 (6)
H5	0.7970	0.4965	0.3601	0.075*
C6	0.5603 (5)	0.44644 (15)	0.44130 (14)	0.0530 (5)
H6	0.5136	0.3945	0.4146	0.064*
C7	0.5646 (4)	0.33550 (13)	0.67278 (11)	0.0385 (4)
C8	0.7127 (4)	0.25923 (12)	0.70866 (10)	0.0372 (4)
C9	0.9251 (5)	0.27975 (16)	0.75383 (12)	0.0493 (5)
H9	0.9790	0.3394	0.7591	0.059*
C10	1.0568 (5)	0.21114 (17)	0.79106 (14)	0.0611 (6)
H10	1.2009	0.2250	0.8207	0.073*
C11	0.9772 (5)	0.12268 (17)	0.78471 (13)	0.0573 (6)
H11	1.0664	0.0770	0.8101	0.069*
C12	0.7650 (5)	0.10229 (14)	0.74057 (13)	0.0557 (5)
H12	0.7084	0.0428	0.7369	0.067*
C13	0.6355 (5)	0.16987 (14)	0.70163 (12)	0.0479 (5)
H13	0.4956	0.1553	0.6705	0.057*
C14	0.9988 (6)	0.64902 (19)	0.41356 (17)	0.0819 (9)
H14A	1.1659	0.6378	0.4355	0.098*
H14B	0.9477	0.7102	0.4242	0.098*
H14C	1.0065	0.6400	0.3591	0.098*
N1	0.4428 (4)	0.31347 (11)	0.60414 (9)	0.0412 (4)
H1N	0.496 (5)	0.2715 (12)	0.5770 (11)	0.049*
O1	0.0820 (3)	0.42621 (11)	0.60730 (9)	0.0558 (4)
O2	0.1517 (3)	0.32651 (11)	0.49499 (9)	0.0572 (4)
O3	0.5488 (3)	0.40946 (10)	0.70188 (9)	0.0540 (4)
S1	0.25282 (10)	0.38263 (3)	0.55513 (3)	0.04071 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0395 (10)	0.0353 (9)	0.0411 (10)	0.0041 (9)	−0.0048 (9)	0.0016 (8)
C2	0.0721 (15)	0.0428 (11)	0.0396 (10)	−0.0038 (10)	−0.0006 (12)	−0.0037 (10)
C3	0.0835 (19)	0.0406 (12)	0.0540 (13)	−0.0141 (12)	−0.0158 (13)	0.0000 (10)
C4	0.0552 (14)	0.0489 (12)	0.0573 (13)	−0.0039 (10)	−0.0093 (11)	0.0136 (11)
C5	0.0709 (15)	0.0597 (13)	0.0559 (13)	−0.0026 (14)	0.0155 (14)	−0.0035 (11)
C6	0.0641 (13)	0.0448 (11)	0.0499 (12)	−0.0061 (11)	0.0065 (12)	−0.0104 (10)
C7	0.0408 (10)	0.0368 (10)	0.0380 (10)	0.0010 (9)	0.0040 (9)	−0.0001 (8)
C8	0.0409 (11)	0.0380 (9)	0.0328 (8)	0.0007 (8)	0.0044 (9)	0.0026 (7)
C9	0.0539 (13)	0.0453 (11)	0.0488 (12)	−0.0076 (11)	−0.0059 (11)	0.0037 (10)
C10	0.0593 (14)	0.0673 (16)	0.0568 (14)	−0.0063 (13)	−0.0160 (13)	0.0132 (12)
C11	0.0621 (14)	0.0585 (13)	0.0514 (12)	0.0065 (12)	−0.0053 (12)	0.0184 (11)
C12	0.0689 (14)	0.0400 (11)	0.0583 (13)	−0.0013 (13)	0.0011 (13)	0.0110 (9)
C13	0.0544 (12)	0.0422 (11)	0.0469 (11)	−0.0034 (10)	−0.0060 (10)	0.0047 (10)
C14	0.080 (2)	0.0802 (19)	0.0857 (19)	−0.0277 (16)	−0.0060 (17)	0.0271 (17)
N1	0.0501 (9)	0.0343 (8)	0.0392 (9)	0.0084 (8)	−0.0036 (8)	−0.0027 (7)
O1	0.0470 (8)	0.0542 (9)	0.0663 (10)	0.0119 (7)	0.0092 (8)	0.0055 (8)
O2	0.0612 (9)	0.0488 (8)	0.0615 (9)	−0.0100 (7)	−0.0204 (8)	−0.0014 (8)
O3	0.0706 (10)	0.0400 (8)	0.0515 (9)	0.0103 (8)	−0.0041 (8)	−0.0096 (7)
S1	0.0389 (2)	0.0368 (2)	0.0464 (3)	0.0022 (2)	−0.0042 (3)	0.0014 (2)

C1—C6	1.379 (3)	C9—C10	1.384 (3)
C1—C2	1.384 (3)	C9—H9	0.9300
C1—S1	1.752 (2)	C10—C11	1.376 (3)
C2—C3	1.378 (3)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.374 (4)
C3—C4	1.388 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.381 (3)
C4—C5	1.382 (3)	C12—H12	0.9300
C4—C14	1.512 (3)	C13—H13	0.9300
C5—C6	1.383 (3)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
C7—O3	1.208 (2)	N1—S1	1.6556 (17)
C7—N1	1.391 (3)	N1—H1N	0.826 (15)
C7—C8	1.500 (3)	O1—S1	1.4224 (16)
C8—C9	1.385 (3)	O2—S1	1.4356 (16)
C8—C13	1.386 (3)
C6—C1—C2	120.2 (2)	C11—C10—C9	120.8 (2)
C6—C1—S1	119.54 (16)	C11—C10—H10	119.6
C2—C1—S1	120.24 (16)	C9—C10—H10	119.6
C3—C2—C1	119.0 (2)	C12—C11—C10	119.5 (2)
C3—C2—H2	120.5	C12—C11—H11	120.2
C1—C2—H2	120.5	C10—C11—H11	120.2
C2—C3—C4	121.8 (2)	C11—C12—C13	120.3 (2)
C2—C3—H3	119.1	C11—C12—H12	119.9
C4—C3—H3	119.1	C13—C12—H12	119.9
C5—C4—C3	118.3 (2)	C12—C13—C8	120.4 (2)
C5—C4—C14	120.4 (2)	C12—C13—H13	119.8
C3—C4—C14	121.3 (2)	C8—C13—H13	119.8
C4—C5—C6	120.7 (2)	C4—C14—H14A	109.5
C4—C5—H5	119.7	C4—C14—H14B	109.5
C6—C5—H5	119.7	H14A—C14—H14B	109.5
C1—C6—C5	120.1 (2)	C4—C14—H14C	109.5
C1—C6—H6	120.0	H14A—C14—H14C	109.5
C5—C6—H6	120.0	H14B—C14—H14C	109.5
O3—C7—N1	122.85 (19)	C7—N1—S1	124.62 (14)
O3—C7—C8	122.68 (18)	C7—N1—H1N	121.2 (17)
N1—C7—C8	114.46 (16)	S1—N1—H1N	111.4 (16)
C9—C8—C13	119.17 (19)	O1—S1—O2	120.16 (11)
C9—C8—C7	118.51 (18)	O1—S1—N1	108.58 (9)
C13—C8—C7	122.21 (19)	O2—S1—N1	103.66 (9)
C10—C9—C8	119.8 (2)	O1—S1—C1	109.86 (9)
C10—C9—H9	120.1	O2—S1—C1	107.93 (10)
C8—C9—H9	120.1	N1—S1—C1	105.62 (10)
C6—C1—C2—C3	−1.4 (3)	C9—C10—C11—C12	0.3 (4)
S1—C1—C2—C3	177.07 (18)	C10—C11—C12—C13	1.3 (4)
C1—C2—C3—C4	0.7 (4)	C11—C12—C13—C8	−2.2 (4)
C2—C3—C4—C5	0.6 (4)	C9—C8—C13—C12	1.5 (3)
C2—C3—C4—C14	−178.1 (2)	C7—C8—C13—C12	−174.8 (2)
C3—C4—C5—C6	−1.2 (4)	O3—C7—N1—S1	−2.5 (3)
C14—C4—C5—C6	177.5 (3)	C8—C7—N1—S1	176.18 (15)
C2—C1—C6—C5	0.8 (4)	C7—N1—S1—O1	−44.6 (2)
S1—C1—C6—C5	−177.7 (2)	C7—N1—S1—O2	−173.41 (17)
C4—C5—C6—C1	0.6 (4)	C7—N1—S1—C1	73.21 (19)
O3—C7—C8—C9	−29.9 (3)	C6—C1—S1—O1	−152.71 (18)
N1—C7—C8—C9	151.34 (18)	C2—C1—S1—O1	28.8 (2)
O3—C7—C8—C13	146.3 (2)	C6—C1—S1—O2	−20.0 (2)
N1—C7—C8—C13	−32.4 (3)	C2—C1—S1—O2	161.54 (17)
C13—C8—C9—C10	0.1 (3)	C6—C1—S1—N1	90.38 (19)
C7—C8—C9—C10	176.5 (2)	C2—C1—S1—N1	−88.08 (18)
C8—C9—C10—C11	−1.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.83 (2)	2.08 (2)	2.905 (2)	175 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.83 (2)	2.08 (2)	2.905 (2)	175 (2)

Symmetry code: (i) .