N-(2-Hy-droxy-phen-yl)-4-methyl-benzene-sulfonamide.

In the title compound, C13H13NO3S, the dihedral angle between the benzene rings is 64.15 (7)° and the C-S-N-C torsion angle is -57.18 (12)°. An intra-molecular N-H⋯O hydrogen bond closes an S(5) ring. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules into C(8) chains propagating in [100]. Weak C-H⋯π inter-actions are also observed.

Related literature

For background to the biological activity of sulfonamide compounds, see: Ozbek et al. (2007 ▶); El-Sayed et al. (2011 ▶). For related structures, see: Gowda et al. (2008a ▶,b ▶,c ▶).

Experimental

Crystal data

C13H13NO3S

M = 263.31

Monoclinic,

a = 7.6780 (1) Å

b = 15.4747 (3) Å

c = 10.7250 (2) Å

β = 104.333 (2)°

V = 1234.62 (4) Å3

Z = 4

Cu Kα radiation

μ = 2.34 mm−1

T = 120 K

0.35 × 0.16 × 0.13 mm

Data collection

Oxford Diffraction SuperNova (Dual, Cu at zero, Atlas) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2013 ▶) T min = 0.494, T max = 0.750

4355 measured reflections

2377 independent reflections

2248 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.082

S = 1.06

2377 reflections

172 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2013 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813033394/hb7173sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033394/hb7173Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813033394/hb7173Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C13H13NO3S	F(000) = 552
Mr = 263.31	Dx = 1.417 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 2248 reflections
a = 7.6780 (1) Å	θ = 5.1–73.2°
b = 15.4747 (3) Å	µ = 2.34 mm−1
c = 10.7250 (2) Å	T = 120 K
β = 104.333 (2)°	Needle, brown
V = 1234.62 (4) Å3	0.35 × 0.16 × 0.13 mm
Z = 4

Oxford Diffraction SuperNova (Dual, Cu at zero, Atlas) diffractometer	2377 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2248 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.011
ω scans	θmax = 73.2°, θmin = 5.1°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2013)	h = −8→9
Tmin = 0.494, Tmax = 0.750	k = −19→12
4355 measured reflections	l = −11→13

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.082	W = 1/[Σ2(FO2) + (0.0424P)2 + 0.5981P] where P = (FO2 + 2FC2)/3
S = 1.06	(Δ/σ)max = 0.001
2377 reflections	Δρmax = 0.28 e Å−3
172 parameters	Δρmin = −0.38 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
S1	0.51287 (4)	0.65871 (2)	0.83597 (3)	0.0203 (1)
O1	0.57618 (13)	0.61174 (7)	0.95358 (10)	0.0281 (3)
O2	0.63687 (13)	0.70958 (7)	0.78545 (10)	0.0267 (3)
O3	0.00824 (14)	0.71635 (7)	0.81974 (10)	0.0264 (3)
N1	0.36177 (15)	0.72621 (8)	0.86360 (11)	0.0208 (3)
C1	0.40408 (17)	0.58685 (9)	0.71468 (13)	0.0196 (4)
C2	0.3833 (2)	0.60851 (9)	0.58584 (14)	0.0239 (4)
C3	0.2974 (2)	0.55124 (10)	0.49170 (14)	0.0268 (4)
C4	0.23172 (19)	0.47243 (9)	0.52309 (14)	0.0247 (4)
C5	0.2521 (2)	0.45305 (10)	0.65261 (15)	0.0278 (4)
C6	0.3373 (2)	0.50922 (10)	0.74888 (14)	0.0253 (4)
C7	0.1447 (2)	0.40915 (11)	0.42031 (17)	0.0343 (5)
C8	0.25492 (18)	0.77847 (9)	0.76315 (13)	0.0192 (3)
C9	0.3290 (2)	0.83739 (9)	0.69307 (15)	0.0243 (4)
C10	0.2174 (2)	0.89020 (9)	0.60237 (15)	0.0273 (4)
C11	0.0320 (2)	0.88327 (10)	0.58080 (14)	0.0265 (4)
C12	−0.04291 (19)	0.82447 (10)	0.65038 (14)	0.0234 (4)
C13	0.06818 (18)	0.77298 (9)	0.74268 (13)	0.0202 (3)
H1N	0.301 (3)	0.7023 (13)	0.9076 (19)	0.035 (5)*
H1O	−0.106 (3)	0.7191 (15)	0.807 (2)	0.051 (6)*
H2	0.42760	0.66200	0.56290	0.0290*
H3	0.28280	0.56590	0.40370	0.0320*
H5	0.20630	0.39990	0.67550	0.0330*
H6	0.35000	0.49500	0.83680	0.0300*
H7A	0.22220	0.35830	0.42470	0.0510*
H7B	0.12710	0.43650	0.33560	0.0510*
H7C	0.02810	0.39140	0.43350	0.0510*
H9	0.45580	0.84160	0.70710	0.0290*
H10	0.26800	0.93100	0.55520	0.0330*
H11	−0.04390	0.91890	0.51810	0.0320*
H12	−0.16980	0.81950	0.63480	0.0280*

	U11	U22	U33	U12	U13	U23
S1	0.0117 (2)	0.0246 (2)	0.0243 (2)	0.0002 (1)	0.0036 (1)	−0.0013 (1)
O1	0.0198 (5)	0.0360 (6)	0.0254 (5)	0.0033 (4)	−0.0005 (4)	0.0019 (4)
O2	0.0140 (5)	0.0298 (5)	0.0380 (6)	−0.0027 (4)	0.0096 (4)	−0.0031 (4)
O3	0.0146 (5)	0.0354 (6)	0.0298 (5)	−0.0019 (4)	0.0068 (4)	0.0060 (4)
N1	0.0150 (5)	0.0253 (6)	0.0229 (6)	−0.0006 (5)	0.0065 (5)	−0.0022 (5)
C1	0.0154 (6)	0.0207 (6)	0.0233 (7)	0.0027 (5)	0.0059 (5)	−0.0003 (5)
C2	0.0258 (7)	0.0208 (7)	0.0269 (7)	0.0013 (5)	0.0101 (6)	0.0031 (5)
C3	0.0308 (8)	0.0275 (7)	0.0232 (7)	0.0035 (6)	0.0089 (6)	0.0008 (6)
C4	0.0197 (6)	0.0247 (7)	0.0302 (7)	0.0040 (6)	0.0071 (6)	−0.0042 (6)
C5	0.0280 (8)	0.0210 (7)	0.0359 (8)	−0.0025 (6)	0.0107 (6)	0.0019 (6)
C6	0.0264 (7)	0.0254 (7)	0.0247 (7)	0.0003 (6)	0.0074 (6)	0.0047 (6)
C7	0.0288 (8)	0.0334 (8)	0.0404 (9)	−0.0004 (7)	0.0081 (7)	−0.0130 (7)
C8	0.0171 (6)	0.0196 (6)	0.0211 (6)	−0.0004 (5)	0.0052 (5)	−0.0056 (5)
C9	0.0206 (7)	0.0230 (7)	0.0319 (7)	−0.0026 (5)	0.0112 (6)	−0.0047 (6)
C10	0.0317 (8)	0.0223 (7)	0.0313 (8)	−0.0011 (6)	0.0144 (6)	0.0009 (6)
C11	0.0292 (8)	0.0243 (7)	0.0260 (7)	0.0048 (6)	0.0069 (6)	0.0001 (6)
C12	0.0178 (6)	0.0268 (7)	0.0255 (7)	0.0018 (5)	0.0051 (5)	−0.0041 (6)
C13	0.0186 (6)	0.0213 (6)	0.0220 (6)	−0.0023 (5)	0.0076 (5)	−0.0050 (5)

S1—O1	1.4325 (11)	C8—C9	1.390 (2)
S1—O2	1.4405 (11)	C9—C10	1.391 (2)
S1—N1	1.6417 (12)	C10—C11	1.389 (2)
S1—C1	1.7574 (14)	C11—C12	1.389 (2)
O3—C13	1.3606 (18)	C12—C13	1.387 (2)
O3—H1O	0.86 (2)	C2—H2	0.9500
N1—C8	1.4318 (18)	C3—H3	0.9500
N1—H1N	0.83 (2)	C5—H5	0.9500
C1—C6	1.391 (2)	C6—H6	0.9500
C1—C2	1.392 (2)	C7—H7A	0.9800
C2—C3	1.382 (2)	C7—H7B	0.9800
C3—C4	1.393 (2)	C7—H7C	0.9800
C4—C7	1.502 (2)	C9—H9	0.9500
C4—C5	1.392 (2)	C10—H10	0.9500
C5—C6	1.384 (2)	C11—H11	0.9500
C8—C13	1.398 (2)	C12—H12	0.9500
O1—S1—O2	119.78 (6)	C11—C12—C13	119.77 (14)
O1—S1—N1	105.36 (6)	O3—C13—C8	115.57 (12)
O1—S1—C1	109.04 (6)	O3—C13—C12	124.25 (13)
O2—S1—N1	106.42 (6)	C8—C13—C12	120.17 (13)
O2—S1—C1	107.74 (6)	C1—C2—H2	120.00
N1—S1—C1	107.97 (6)	C3—C2—H2	120.00
C13—O3—H1O	111.0 (15)	C2—C3—H3	119.00
S1—N1—C8	121.50 (9)	C4—C3—H3	119.00
C8—N1—H1N	112.5 (15)	C4—C5—H5	119.00
S1—N1—H1N	110.0 (15)	C6—C5—H5	119.00
S1—C1—C6	119.35 (11)	C1—C6—H6	121.00
S1—C1—C2	119.94 (11)	C5—C6—H6	121.00
C2—C1—C6	120.71 (13)	C4—C7—H7A	109.00
C1—C2—C3	119.17 (13)	C4—C7—H7B	109.00
C2—C3—C4	121.39 (14)	C4—C7—H7C	109.00
C5—C4—C7	120.78 (13)	H7A—C7—H7B	109.00
C3—C4—C5	118.17 (13)	H7A—C7—H7C	109.00
C3—C4—C7	121.03 (13)	H7B—C7—H7C	109.00
C4—C5—C6	121.67 (14)	C8—C9—H9	120.00
C1—C6—C5	118.87 (13)	C10—C9—H9	120.00
N1—C8—C9	122.85 (13)	C9—C10—H10	120.00
N1—C8—C13	117.26 (12)	C11—C10—H10	120.00
C9—C8—C13	119.73 (13)	C10—C11—H11	120.00
C8—C9—C10	119.99 (14)	C12—C11—H11	120.00
C9—C10—C11	119.98 (14)	C11—C12—H12	120.00
C10—C11—C12	120.33 (14)	C13—C12—H12	120.00
O1—S1—N1—C8	−173.59 (11)	C2—C3—C4—C7	−177.69 (15)
O2—S1—N1—C8	58.25 (12)	C2—C3—C4—C5	1.0 (2)
C1—S1—N1—C8	−57.18 (12)	C3—C4—C5—C6	−1.0 (2)
O1—S1—C1—C2	−158.83 (12)	C7—C4—C5—C6	177.79 (15)
O2—S1—C1—C2	−27.38 (14)	C4—C5—C6—C1	−0.1 (2)
N1—S1—C1—C2	87.19 (13)	N1—C8—C9—C10	−175.85 (13)
O1—S1—C1—C6	22.08 (14)	C13—C8—C9—C10	−0.4 (2)
O2—S1—C1—C6	153.53 (12)	N1—C8—C13—O3	−1.43 (18)
N1—S1—C1—C6	−91.91 (13)	N1—C8—C13—C12	177.40 (13)
S1—N1—C8—C9	−59.30 (17)	C9—C8—C13—O3	−177.10 (13)
S1—N1—C8—C13	125.18 (12)	C9—C8—C13—C12	1.7 (2)
S1—C1—C6—C5	−179.91 (12)	C8—C9—C10—C11	−0.8 (2)
S1—C1—C2—C3	−180.00 (12)	C9—C10—C11—C12	0.7 (2)
C6—C1—C2—C3	−0.9 (2)	C10—C11—C12—C13	0.6 (2)
C2—C1—C6—C5	1.0 (2)	C11—C12—C13—O3	176.92 (13)
C1—C2—C3—C4	−0.1 (2)	C11—C12—C13—C8	−1.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.83 (2)	2.22 (2)	2.6420 (16)	111.6 (17)
O3—H1O···O2i	0.86 (2)	1.94 (2)	2.7852 (15)	172 (2)
C9—H9···O2	0.95	2.50	3.0531 (18)	117
C3—H3···Cg2ii	0.95	2.92	3.8022 (16)	155
C7—H7C···Cg1iii	0.98	2.85	3.5937 (17)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3	0.83 (2)	2.22 (2)	2.6420 (16)	111.6 (17)
O3—H1O⋯O2i	0.86 (2)	1.94 (2)	2.7852 (15)	172 (2)
C3—H3⋯Cg2ii	0.95	2.92	3.8022 (16)	155
C7—H7C⋯Cg1iii	0.98	2.85	3.5937 (17)	134

Symmetry codes: (i) ; (ii) ; (iii) .