N-(2-Formyl-phen-yl)benzene-sulfonamide.

In the title compound, C(13)H(11)NO(3)S, the two aromatic rings are oriented at an angle of 88.18 (8)°. Intra-molecular N-H⋯O and C-H⋯O hydrogen bonds are observed, each of which generates an S(6) ring motif. In the crystal, mol-ecules are linked into C(7) chains along [010] by inter-molecular C-H⋯O hydrogen bonds. The structure is further stabilized by inter-molecular C-H⋯π inter-actions involving the sulfonyl-bound phenyl ring.

Related literature

For the biological activity of sulfonamides, see: Zareef et al. (2007 ▶); Chohan et al. (2007 ▶); Brown (1971 ▶); Pomarnacka & Kozlarska-Kedra (2003 ▶); Sethu Sankar et al. (2002 ▶). For related structures, see: Bassindale (1984 ▶); Cotton & Stokley (1970 ▶); Usha et al. (2005 ▶); Zhu et al. (2008 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H11NO3S

M = 261.29

Triclinic,

a = 7.7656 (2) Å

b = 9.0080 (2) Å

c = 9.5855 (2) Å

α = 86.293 (1)°

β = 77.912 (1)°

γ = 68.826 (1)°

V = 611.35 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 293 K

0.21 × 0.19 × 0.17 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.768, T max = 0.956

15490 measured reflections

3960 independent reflections

3228 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.119

S = 1.02

3960 reflections

167 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032681/ci2869sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032681/ci2869Isup2.hkl

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

C13H11NO3S	Z = 2
Mr = 261.29	F(000) = 272
Triclinic, P1	Dx = 1.419 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7656 (2) Å	Cell parameters from 3960 reflections
b = 9.0080 (2) Å	θ = 2.2–31.3°
c = 9.5855 (2) Å	µ = 0.26 mm−1
α = 86.293 (1)°	T = 293 K
β = 77.912 (1)°	Block, colourless
γ = 68.826 (1)°	0.21 × 0.19 × 0.17 mm
V = 611.35 (2) Å3

Bruker Kappa APEXII CCD diffractometer	3960 independent reflections
Radiation source: fine-focus sealed tube	3228 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω scans	θmax = 31.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.768, Tmax = 0.956	k = −13→13
15490 measured reflections	l = −13→13

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0582P)2 + 0.1353P] where P = (Fo2 + 2Fc2)/3
3960 reflections	(Δ/σ)max = 0.001
167 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.31 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	0.19429 (17)	0.98956 (14)	0.61966 (13)	0.0409 (2)
C2	0.1595 (2)	1.10035 (15)	0.72614 (15)	0.0470 (3)
H2	0.1207	1.0779	0.8210	0.056*
C3	0.1827 (2)	1.24378 (17)	0.69056 (18)	0.0563 (3)
H3	0.1595	1.3170	0.7626	0.068*
C4	0.2392 (3)	1.2813 (2)	0.5513 (2)	0.0695 (5)
H4	0.2547	1.3783	0.5292	0.083*
C5	0.2722 (3)	1.1734 (2)	0.44619 (19)	0.0675 (4)
H5	0.3085	1.1987	0.3517	0.081*
C6	0.2529 (2)	1.02670 (18)	0.47720 (15)	0.0503 (3)
C7	0.2926 (3)	0.9189 (3)	0.35857 (18)	0.0692 (5)
H7	0.3264	0.9554	0.2677	0.083*
C8	0.36455 (18)	0.70690 (14)	0.85278 (13)	0.0413 (3)
C9	0.5123 (2)	0.57064 (16)	0.79634 (16)	0.0519 (3)
H9	0.4963	0.5055	0.7325	0.062*
C10	0.6827 (2)	0.5337 (2)	0.83658 (19)	0.0628 (4)
H10	0.7829	0.4425	0.7999	0.075*
C11	0.7062 (2)	0.6304 (2)	0.93052 (19)	0.0621 (4)
H11	0.8225	0.6047	0.9563	0.074*
C12	0.5587 (2)	0.7649 (2)	0.98675 (18)	0.0599 (4)
H12	0.5758	0.8296	1.0503	0.072*
C13	0.3853 (2)	0.80416 (16)	0.94909 (15)	0.0487 (3)
H13	0.2847	0.8941	0.9877	0.058*
N1	0.16942 (19)	0.84378 (14)	0.64708 (14)	0.0509 (3)
O1	0.00479 (14)	0.85915 (13)	0.90061 (12)	0.0576 (3)
O2	0.13222 (17)	0.60899 (13)	0.76162 (14)	0.0649 (3)
O3	0.2861 (2)	0.78653 (18)	0.36620 (14)	0.0795 (4)
S1	0.14948 (5)	0.75289 (4)	0.79852 (4)	0.04575 (11)
H1	0.199 (3)	0.790 (2)	0.5767 (19)	0.064 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0388 (6)	0.0369 (5)	0.0461 (6)	−0.0096 (4)	−0.0123 (5)	−0.0046 (5)
C2	0.0562 (7)	0.0365 (6)	0.0482 (7)	−0.0149 (5)	−0.0113 (6)	−0.0055 (5)
C3	0.0638 (9)	0.0377 (6)	0.0699 (9)	−0.0173 (6)	−0.0180 (7)	−0.0056 (6)
C4	0.0839 (12)	0.0498 (8)	0.0803 (11)	−0.0310 (8)	−0.0182 (10)	0.0112 (8)
C5	0.0769 (11)	0.0679 (10)	0.0581 (9)	−0.0294 (9)	−0.0116 (8)	0.0132 (8)
C6	0.0475 (7)	0.0533 (8)	0.0471 (7)	−0.0125 (6)	−0.0117 (6)	−0.0036 (6)
C7	0.0711 (10)	0.0802 (12)	0.0485 (8)	−0.0171 (9)	−0.0081 (7)	−0.0160 (8)
C8	0.0431 (6)	0.0316 (5)	0.0466 (6)	−0.0155 (4)	0.0004 (5)	0.0003 (4)
C9	0.0505 (7)	0.0380 (6)	0.0589 (8)	−0.0127 (5)	0.0027 (6)	−0.0044 (5)
C10	0.0474 (7)	0.0506 (8)	0.0725 (10)	−0.0056 (6)	0.0036 (7)	0.0057 (7)
C11	0.0481 (7)	0.0680 (10)	0.0680 (9)	−0.0209 (7)	−0.0118 (7)	0.0184 (8)
C12	0.0638 (9)	0.0618 (9)	0.0604 (9)	−0.0276 (7)	−0.0175 (7)	0.0038 (7)
C13	0.0518 (7)	0.0414 (6)	0.0511 (7)	−0.0160 (5)	−0.0062 (6)	−0.0039 (5)
N1	0.0662 (7)	0.0391 (5)	0.0508 (6)	−0.0199 (5)	−0.0134 (5)	−0.0108 (5)
O1	0.0440 (5)	0.0534 (6)	0.0689 (7)	−0.0164 (4)	0.0051 (5)	−0.0129 (5)
O2	0.0657 (7)	0.0436 (5)	0.0938 (8)	−0.0315 (5)	−0.0089 (6)	−0.0106 (5)
O3	0.0860 (9)	0.0802 (9)	0.0672 (8)	−0.0192 (7)	−0.0129 (7)	−0.0333 (7)
S1	0.04451 (18)	0.03489 (16)	0.0591 (2)	−0.01869 (12)	−0.00239 (14)	−0.00769 (12)

C1—C2	1.3900 (17)	C8—C9	1.3871 (18)
C1—N1	1.3957 (17)	C8—S1	1.7515 (14)
C1—C6	1.4052 (19)	C9—C10	1.375 (2)
C2—C3	1.3797 (19)	C9—H9	0.93
C2—H2	0.93	C10—C11	1.374 (3)
C3—C4	1.375 (2)	C10—H10	0.93
C3—H3	0.93	C11—C12	1.376 (2)
C4—C5	1.365 (3)	C11—H11	0.93
C4—H4	0.93	C12—C13	1.383 (2)
C5—C6	1.390 (2)	C12—H12	0.93
C5—H5	0.93	C13—H13	0.93
C6—C7	1.453 (2)	N1—S1	1.6265 (13)
C7—O3	1.208 (2)	N1—H1	0.798 (18)
C7—H7	0.93	O1—S1	1.4212 (10)
C8—C13	1.3838 (18)	O2—S1	1.4241 (10)
C2—C1—N1	123.02 (12)	C10—C9—C8	118.75 (15)
C2—C1—C6	118.86 (12)	C10—C9—H9	120.6
N1—C1—C6	118.10 (12)	C8—C9—H9	120.6
C3—C2—C1	119.78 (14)	C11—C10—C9	120.54 (15)
C3—C2—H2	120.1	C11—C10—H10	119.7
C1—C2—H2	120.1	C9—C10—H10	119.7
C4—C3—C2	121.69 (15)	C10—C11—C12	120.40 (15)
C4—C3—H3	119.2	C10—C11—H11	119.8
C2—C3—H3	119.2	C12—C11—H11	119.8
C5—C4—C3	118.78 (15)	C11—C12—C13	120.29 (16)
C5—C4—H4	120.6	C11—C12—H12	119.9
C3—C4—H4	120.6	C13—C12—H12	119.9
C4—C5—C6	121.51 (16)	C12—C13—C8	118.66 (14)
C4—C5—H5	119.2	C12—C13—H13	120.7
C6—C5—H5	119.2	C8—C13—H13	120.7
C5—C6—C1	119.37 (14)	C1—N1—S1	128.49 (9)
C5—C6—C7	117.69 (16)	C1—N1—H1	112.3 (14)
C1—C6—C7	122.94 (15)	S1—N1—H1	116.5 (13)
O3—C7—C6	126.49 (17)	O1—S1—O2	119.76 (7)
O3—C7—H7	116.8	O1—S1—N1	109.04 (7)
C6—C7—H7	116.8	O2—S1—N1	103.70 (7)
C13—C8—C9	121.35 (13)	O1—S1—C8	108.57 (7)
C13—C8—S1	120.66 (10)	O2—S1—C8	108.83 (7)
C9—C8—S1	117.98 (11)	N1—S1—C8	106.08 (6)
N1—C1—C2—C3	−178.37 (13)	C9—C10—C11—C12	0.6 (2)
C6—C1—C2—C3	0.1 (2)	C10—C11—C12—C13	−0.1 (2)
C1—C2—C3—C4	0.2 (2)	C11—C12—C13—C8	−0.9 (2)
C2—C3—C4—C5	0.3 (3)	C9—C8—C13—C12	1.3 (2)
C3—C4—C5—C6	−1.1 (3)	S1—C8—C13—C12	−178.76 (11)
C4—C5—C6—C1	1.4 (3)	C2—C1—N1—S1	−16.6 (2)
C4—C5—C6—C7	−179.47 (18)	C6—C1—N1—S1	164.92 (11)
C2—C1—C6—C5	−0.8 (2)	C1—N1—S1—O1	52.78 (14)
N1—C1—C6—C5	177.67 (14)	C1—N1—S1—O2	−178.56 (12)
C2—C1—C6—C7	−179.97 (14)	C1—N1—S1—C8	−63.97 (14)
N1—C1—C6—C7	−1.4 (2)	C13—C8—S1—O1	−19.79 (13)
C5—C6—C7—O3	178.68 (18)	C9—C8—S1—O1	160.20 (10)
C1—C6—C7—O3	−2.2 (3)	C13—C8—S1—O2	−151.70 (11)
C13—C8—C9—C10	−0.7 (2)	C9—C8—S1—O2	28.29 (13)
S1—C8—C9—C10	179.30 (11)	C13—C8—S1—N1	97.27 (11)
C8—C9—C10—C11	−0.2 (2)	C9—C8—S1—N1	−82.73 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.80 (2)	1.99 (2)	2.6751 (19)	144 (2)
C2—H2···O1	0.93	2.46	3.0879 (18)	125
C3—H3···O2i	0.93	2.56	3.2691 (19)	133
C5—H5···Cg1ii	0.93	2.80	3.700 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3	0.80 (2)	1.99 (2)	2.6751 (19)	144 (2)
C2—H2⋯O1	0.93	2.46	3.0879 (18)	125
C3—H3⋯O2i	0.93	2.56	3.2691 (19)	133
C5—H5⋯Cg1ii	0.93	2.80	3.700 (2)	162

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C8–C13 ring.