N-Benzo-ylbenzene-sulfonamide.

In the crystal structure of the title compound, C(13)H(11)NO(3)S, the conformation of the N-H bond in the C-SO(2)-NH-C(O)-C segment is anti to the C=O bond. The molecule is twisted at theN atom with a dihedral angle of 86.5(1)° between the sulfonyl benzene ring and the -SO(2)-NH-C=O segment. Furthermore, the dihedral angle between the two benzene rings is 80.3(1)°. The crystal structure features inversion-related dimers linked by pairs of N-H⋯O(S) hydrogen bonds.

Related literature

For related structures, see: Gowda et al. (2008a ▶,b ▶; 2009 ▶).

Experimental

Crystal data

C13H11NO3S

M = 261.29

Triclinic,

a = 5.8396 (7) Å

b = 10.178 (1) Å

c = 10.405 (1) Å

α = 90.187 (8)°

β = 99.074 (9)°

γ = 99.617 (9)°

V = 601.83 (11) Å3

Z = 2

Cu Kα radiation

μ = 2.40 mm−1

T = 299 K

0.50 × 0.33 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan North et al., 1968 ▶ T min = 0.380, T max = 0.889

2354 measured reflections

2125 independent reflections

1962 reflections with I > 2σ(I)

R int = 0.011

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

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.171

S = 1.18

2125 reflections

167 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.65 e Å−3

Δρmin = −0.36 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, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809037222/tk2540sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037222/tk2540Isup2.hkl

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

C13H11NO3S	Z = 2
Mr = 261.29	F(000) = 272
Triclinic, P1	Dx = 1.442 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 5.8396 (7) Å	Cell parameters from 25 reflections
b = 10.178 (1) Å	θ = 4.3–22.9°
c = 10.405 (1) Å	µ = 2.40 mm−1
α = 90.187 (8)°	T = 299 K
β = 99.074 (9)°	Long plate, colorless
γ = 99.617 (9)°	0.50 × 0.33 × 0.05 mm
V = 601.83 (11) Å3

Enraf–Nonius CAD-4 diffractometer	1962 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.011
graphite	θmax = 66.9°, θmin = 4.3°
ω/2θ scans	h = 0→6
Absorption correction: ψ scan North et al., 1968	k = −12→11
Tmin = 0.380, Tmax = 0.889	l = −12→12
2354 measured reflections	3 standard reflections every 120 min
2125 independent reflections	intensity decay: 1.0%

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)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.171	w = 1/[σ2(Fo2) + (0.0862P)2 + 0.5464P] where P = (Fo2 + 2Fc2)/3
S = 1.18	(Δ/σ)max = 0.008
2125 reflections	Δρmax = 0.65 e Å−3
167 parameters	Δρmin = −0.36 e Å−3
7 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (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	0.3607 (5)	0.8198 (3)	0.8908 (3)	0.0337 (6)
C2	0.2344 (5)	0.9229 (3)	0.8901 (3)	0.0407 (7)
H2	0.1021	0.9143	0.9307	0.049*
C3	0.3058 (7)	1.0380 (3)	0.8289 (4)	0.0539 (9)
H3	0.2219	1.1081	0.8283	0.065*
C4	0.5004 (7)	1.0503 (4)	0.7686 (4)	0.0589 (10)
H4	0.5482	1.1288	0.7274	0.071*
C5	0.6248 (6)	0.9472 (4)	0.7688 (4)	0.0583 (10)
H5	0.7553	0.9559	0.7266	0.070*
C6	0.5584 (5)	0.8304 (4)	0.8311 (3)	0.0470 (8)
H6	0.6442	0.7611	0.8329	0.056*
C7	0.0114 (5)	0.5480 (3)	0.7670 (3)	0.0400 (7)
C8	−0.0390 (5)	0.4316 (3)	0.6753 (3)	0.0368 (7)
C9	−0.2525 (6)	0.4135 (4)	0.5908 (3)	0.0500 (8)
H9	−0.3577	0.4717	0.5965	0.060*
C10	−0.3098 (6)	0.3115 (4)	0.4997 (4)	0.0602 (10)
H10	−0.4533	0.3009	0.4441	0.072*
C11	−0.1570 (7)	0.2248 (4)	0.4897 (4)	0.0564 (9)
H11	−0.1958	0.1557	0.4273	0.068*
C12	0.0539 (7)	0.2408 (4)	0.5727 (4)	0.0589 (10)
H12	0.1576	0.1818	0.5664	0.071*
C13	0.1137 (6)	0.3429 (4)	0.6649 (3)	0.0492 (8)
H13	0.2571	0.3526	0.7205	0.059*
N1	0.2045 (5)	0.5551 (3)	0.8642 (3)	0.0436 (7)
H1N	0.262 (7)	0.491 (3)	0.882 (4)	0.052*
O1	0.4799 (5)	0.6424 (2)	1.0568 (3)	0.0629 (8)
O2	0.0786 (5)	0.6940 (3)	1.0349 (3)	0.0597 (7)
O3	−0.1033 (4)	0.6374 (3)	0.7564 (3)	0.0562 (7)
S1	0.27661 (14)	0.67612 (7)	0.97654 (7)	0.0416 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0246 (13)	0.0344 (14)	0.0396 (15)	0.0060 (10)	−0.0030 (11)	−0.0037 (11)
C2	0.0305 (15)	0.0399 (16)	0.0508 (18)	0.0101 (12)	−0.0009 (12)	−0.0029 (13)
C3	0.054 (2)	0.0397 (17)	0.064 (2)	0.0116 (15)	−0.0085 (17)	0.0005 (15)
C4	0.057 (2)	0.049 (2)	0.058 (2)	−0.0084 (16)	−0.0088 (18)	0.0092 (16)
C5	0.0344 (17)	0.081 (3)	0.054 (2)	−0.0073 (17)	0.0082 (15)	−0.0003 (18)
C6	0.0320 (16)	0.059 (2)	0.0508 (18)	0.0136 (14)	0.0041 (13)	−0.0049 (15)
C7	0.0280 (15)	0.0441 (17)	0.0469 (17)	0.0057 (12)	0.0030 (12)	0.0036 (13)
C8	0.0280 (14)	0.0415 (16)	0.0392 (15)	0.0050 (11)	0.0013 (11)	0.0046 (12)
C9	0.0314 (16)	0.063 (2)	0.0534 (19)	0.0125 (14)	−0.0044 (14)	−0.0042 (16)
C10	0.0408 (19)	0.076 (3)	0.056 (2)	0.0057 (17)	−0.0116 (16)	−0.0082 (18)
C11	0.061 (2)	0.056 (2)	0.0469 (19)	0.0034 (17)	−0.0017 (16)	−0.0092 (16)
C12	0.061 (2)	0.062 (2)	0.055 (2)	0.0257 (18)	−0.0035 (17)	−0.0090 (17)
C13	0.0401 (17)	0.056 (2)	0.0486 (18)	0.0154 (14)	−0.0082 (14)	−0.0067 (15)
N1	0.0414 (15)	0.0331 (13)	0.0525 (16)	0.0104 (11)	−0.0086 (12)	0.0001 (12)
O1	0.0787 (18)	0.0431 (13)	0.0567 (15)	0.0186 (12)	−0.0293 (13)	−0.0018 (11)
O2	0.0647 (16)	0.0593 (15)	0.0575 (15)	0.0008 (12)	0.0278 (13)	−0.0007 (12)
O3	0.0414 (13)	0.0604 (15)	0.0686 (16)	0.0248 (11)	−0.0031 (11)	−0.0111 (12)
S1	0.0460 (5)	0.0348 (5)	0.0405 (5)	0.0062 (3)	−0.0023 (3)	0.0006 (3)

C1—C2	1.379 (4)	C8—C13	1.385 (5)
C1—C6	1.384 (4)	C8—C9	1.392 (4)
C1—S1	1.756 (3)	C9—C10	1.366 (5)
C2—C3	1.370 (5)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.370 (6)
C3—C4	1.370 (6)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.373 (5)
C4—C5	1.373 (6)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.375 (5)
C5—C6	1.383 (5)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	N1—S1	1.650 (3)
C7—O3	1.212 (4)	N1—H1N	0.79 (3)
C7—N1	1.383 (4)	O1—S1	1.432 (2)
C7—C8	1.479 (4)	O2—S1	1.425 (3)
C2—C1—C6	121.3 (3)	C10—C9—C8	121.0 (3)
C2—C1—S1	119.0 (2)	C10—C9—H9	119.5
C6—C1—S1	119.6 (2)	C8—C9—H9	119.5
C3—C2—C1	119.4 (3)	C9—C10—C11	120.4 (3)
C3—C2—H2	120.3	C9—C10—H10	119.8
C1—C2—H2	120.3	C11—C10—H10	119.8
C4—C3—C2	120.3 (3)	C10—C11—C12	119.4 (3)
C4—C3—H3	119.9	C10—C11—H11	120.3
C2—C3—H3	119.9	C12—C11—H11	120.3
C3—C4—C5	120.2 (3)	C11—C12—C13	120.8 (3)
C3—C4—H4	119.9	C11—C12—H12	119.6
C5—C4—H4	119.9	C13—C12—H12	119.6
C4—C5—C6	120.8 (3)	C12—C13—C8	120.2 (3)
C4—C5—H5	119.6	C12—C13—H13	119.9
C6—C5—H5	119.6	C8—C13—H13	119.9
C1—C6—C5	118.1 (3)	C7—N1—S1	122.6 (2)
C1—C6—H6	121.0	C7—N1—H1N	120 (3)
C5—C6—H6	121.0	S1—N1—H1N	114 (3)
O3—C7—N1	120.1 (3)	O2—S1—O1	119.09 (18)
O3—C7—C8	122.6 (3)	O2—S1—N1	110.97 (15)
N1—C7—C8	117.2 (3)	O1—S1—N1	103.63 (14)
C13—C8—C9	118.2 (3)	O2—S1—C1	108.38 (15)
C13—C8—C7	124.8 (3)	O1—S1—C1	109.23 (15)
C9—C8—C7	117.0 (3)	N1—S1—C1	104.55 (14)
C6—C1—C2—C3	0.1 (5)	C10—C11—C12—C13	−0.3 (6)
S1—C1—C2—C3	176.8 (2)	C11—C12—C13—C8	0.0 (6)
C1—C2—C3—C4	0.2 (5)	C9—C8—C13—C12	0.3 (5)
C2—C3—C4—C5	0.1 (5)	C7—C8—C13—C12	−177.3 (3)
C3—C4—C5—C6	−0.9 (5)	O3—C7—N1—S1	5.1 (4)
C2—C1—C6—C5	−0.9 (5)	C8—C7—N1—S1	−177.7 (2)
S1—C1—C6—C5	−177.5 (2)	C7—N1—S1—O2	49.8 (3)
C4—C5—C6—C1	1.3 (5)	C7—N1—S1—O1	178.7 (3)
O3—C7—C8—C13	164.9 (3)	C7—N1—S1—C1	−66.9 (3)
N1—C7—C8—C13	−12.2 (5)	C2—C1—S1—O2	−0.3 (3)
O3—C7—C8—C9	−12.7 (5)	C6—C1—S1—O2	176.3 (2)
N1—C7—C8—C9	170.2 (3)	C2—C1—S1—O1	−131.5 (2)
C13—C8—C9—C10	−0.3 (5)	C6—C1—S1—O1	45.2 (3)
C7—C8—C9—C10	177.5 (3)	C2—C1—S1—N1	118.1 (2)
C8—C9—C10—C11	−0.1 (6)	C6—C1—S1—N1	−65.2 (3)
C9—C10—C11—C12	0.3 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.79 (3)	2.22 (3)	2.981 (4)	163 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.79 (3)	2.22 (3)	2.981 (4)	163 (4)

Symmetry code: (i) .