N-(4-Hydroxy­phen­yl)benzene­sulfon­amide

Khan, I.U.; Mariam, I.; Zia-ur-Rehman, M.; Arif Sajjad, M.; Sharif, S.

doi:10.1107/S160053681001322X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1088

https://doi.org/10.1107/S160053681001322X

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N-(4-Hydroxyphenyl)benzenesulfonamide

Islam Ullah Khan,^a Irfana Mariam,^a Muhammad Zia-ur-Rehman,^b ^* Muhammad Arif Sajjad ^a and Shahzad Sharif ^a

^aMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore 54000, Pakistan, and ^bApplied Chemistry Research Centre, PCSIR Laboratories Complex, Lahore 54600, Pakistan
^*Correspondence e-mail: rehman_pcsir@hotmail.com

(Received 31 March 2010; accepted 9 April 2010; online 14 April 2010)

The title compound, C₁₂H₁₁NO₃S, synthesized by the reaction of benzene sulfonyl chloride with para-aminophenol, is of interest as a precursor to biologically active sulfur-containing heterocyclic compounds. The structure is stabilized by N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For the synthesis of related molecules, see: Zia-ur-Rehman et al. (2006 , 2009 ). For a related structure, see: Khan et al. (2009 ).

Experimental

Crystal data

C₁₂H₁₁NO₃S
M_r = 249.28
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.1072 (2) Å
b = 9.3948 (4) Å
c = 24.0903 (10) Å
V = 1155.88 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 296 K
0.12 × 0.12 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
6402 measured reflections
2808 independent reflections
2076 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.146
S = 1.02
2808 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983 ), with 1118 Friedel pairs
Flack parameter: 0.08 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.96	2.07	3.030 (3)	173
O3—H3⋯O1ⁱⁱ	0.82	2.05	2.857 (4)	166
Symmetry codes: (i) x-1, y, z; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681001322X/bt5239sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681001322X/bt5239Isup2.hkl

checkCIF report

Comment top

In the present paper, the structure of N-(4-hydroxyphenyl) benzene sulfonamide (Fig. 1) has been determined as part of a research program involving the synthesis and biological evaluation of sulfur containing heterocyclic compounds (Zia-ur-Rehman et al., 2006, 2009; Khan et al., 2009). Bond lengths and bond angles are almost similar to those in the related molecules (Khan et al., 2009). The molecules are linked through intermolecular N—H···O and O—H···O hydrogen bonds (Fig. 2; Table 1).

Related literature top

For the synthesis of related molecules, see: Zia-ur-Rehman et al. (2006, 2009). For a related structure, see: Khan et al. (2009).

Experimental top

A mixture of benzene sulfonyl chloride (10.0 mmoles; 1.766 g), para-aminophenol (10.0 mmoles; 1.286 g), aqueous sodium carbonate (10%; 10.0 ml) and water (25 ml) was stirred for half an hour at room temperature followed by evaporation of the solvent. The crude mixture was washed with water and dried. Product obtained was dissolved in methanol and crystallized by slow evaporation of the solvent. Yield 73%.

Structure description top

For the synthesis of related molecules, see: Zia-ur-Rehman et al. (2006, 2009). For a related structure, see: Khan et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids at the 50% probability level.
	Fig. 2. Perspective view of the three-dimensional crystal packing showing hydrogen-bonded interactions (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.

N-(4-Hydroxyphenyl)benzenesulfonamide top

Crystal data top

C₁₂H₁₁NO₃S	F(000) = 520
M_r = 249.28	D_x = 1.432 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6462 reflections
a = 5.1072 (2) Å	θ = 2.5–27.1°
b = 9.3948 (4) Å	µ = 0.28 mm⁻¹
c = 24.0903 (10) Å	T = 296 K
V = 1155.88 (8) Å³	Needle, colourless
Z = 4	0.12 × 0.12 × 0.10 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2076 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 28.3°, θ_min = 1.7°
φ and ω scans	h = −4→6
6402 measured reflections	k = −8→12
2808 independent reflections	l = −32→32

Refinement top

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)] = 0.048	H-atom parameters constrained
wR(F²) = 0.146	w = 1/[σ²(F_o²) + (0.0829P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2808 reflections	Δρ_max = 0.26 e Å⁻³
155 parameters	Δρ_min = −0.26 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1118 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.08 (13)

Crystal data top

C₁₂H₁₁NO₃S	V = 1155.88 (8) Å³
M_r = 249.28	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.1072 (2) Å	µ = 0.28 mm⁻¹
b = 9.3948 (4) Å	T = 296 K
c = 24.0903 (10) Å	0.12 × 0.12 × 0.10 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2076 reflections with I > 2σ(I)
6402 measured reflections	R_int = 0.032
2808 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.146	Δρ_max = 0.26 e Å⁻³
S = 1.02	Δρ_min = −0.26 e Å⁻³
2808 reflections	Absolute structure: Flack (1983), 1118 Friedel pairs
155 parameters	Absolute structure parameter: 0.08 (13)
0 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.63260 (16)	0.61227 (9)	0.12889 (3)	0.0363 (2)
O1	0.5233 (5)	0.7519 (3)	0.13349 (12)	0.0522 (7)
N1	0.4626 (5)	0.5129 (3)	0.17054 (11)	0.0370 (7)
C1	0.4079 (7)	0.2576 (4)	0.15217 (13)	0.0395 (8)
H1	0.2692	0.2783	0.1285	0.047*
O2	0.9034 (4)	0.5892 (3)	0.14085 (9)	0.0485 (6)
C2	0.4814 (6)	0.1180 (4)	0.16065 (13)	0.0431 (8)
H2	0.3893	0.0445	0.1437	0.052*
O3	0.7825 (6)	−0.0468 (3)	0.20338 (12)	0.0585 (8)
H3	0.6871	−0.1039	0.1874	0.088*
C3	0.6923 (7)	0.0881 (4)	0.19449 (13)	0.0396 (8)
C4	0.8231 (7)	0.1962 (4)	0.22069 (14)	0.0433 (9)
H4	0.9647	0.1759	0.2437	0.052*
C5	0.7442 (7)	0.3353 (4)	0.21288 (14)	0.0402 (8)
H5	0.8313	0.4087	0.2311	0.048*
C6	0.5380 (6)	0.3661 (4)	0.17841 (12)	0.0321 (7)
C7	0.5766 (6)	0.5525 (4)	0.06026 (12)	0.0351 (7)
C8	0.3782 (7)	0.6111 (4)	0.02947 (14)	0.0493 (8)
H8	0.2742	0.6831	0.0442	0.059*
C9	0.3350 (8)	0.5617 (5)	−0.02374 (15)	0.0595 (11)
H9	0.2018	0.6009	−0.0452	0.071*
C10	0.4879 (8)	0.4549 (5)	−0.04506 (15)	0.0598 (11)
H10	0.4584	0.4225	−0.0810	0.072*
C11	0.6818 (8)	0.3963 (5)	−0.01419 (16)	0.0662 (12)
H11	0.7834	0.3233	−0.0289	0.079*
C12	0.7288 (7)	0.4448 (4)	0.03900 (14)	0.0507 (9)
H12	0.8620	0.4049	0.0602	0.061*
H1N	0.2803	0.5303	0.1630	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0375 (4)	0.0329 (4)	0.0385 (4)	−0.0016 (4)	−0.0041 (3)	−0.0002 (4)
O1	0.0636 (17)	0.0303 (12)	0.0625 (16)	0.0040 (12)	−0.0060 (14)	−0.0046 (12)
N1	0.0364 (15)	0.0373 (15)	0.0373 (13)	0.0033 (12)	0.0024 (11)	0.0021 (13)
C1	0.0377 (18)	0.0422 (19)	0.0385 (16)	0.0000 (16)	−0.0116 (14)	0.0006 (15)
O2	0.0358 (13)	0.0577 (16)	0.0519 (13)	−0.0093 (12)	−0.0081 (11)	0.0039 (12)
C2	0.0430 (18)	0.0401 (18)	0.0463 (17)	−0.0019 (17)	−0.0108 (14)	−0.0059 (18)
O3	0.072 (2)	0.0341 (14)	0.0689 (18)	0.0048 (14)	−0.0216 (14)	0.0013 (14)
C3	0.048 (2)	0.0371 (19)	0.0340 (16)	0.0018 (16)	−0.0018 (13)	0.0043 (15)
C4	0.046 (2)	0.045 (2)	0.0395 (17)	−0.0033 (17)	−0.0152 (16)	0.0063 (16)
C5	0.0486 (19)	0.0345 (18)	0.0375 (16)	−0.0059 (17)	−0.0104 (15)	0.0008 (15)
C6	0.0352 (15)	0.0326 (17)	0.0284 (13)	0.0008 (14)	0.0042 (12)	0.0024 (13)
C7	0.0345 (17)	0.0343 (17)	0.0364 (15)	−0.0052 (14)	0.0005 (13)	0.0036 (14)
C8	0.0475 (19)	0.050 (2)	0.0504 (19)	0.004 (2)	−0.0062 (17)	0.0066 (18)
C9	0.060 (3)	0.073 (3)	0.046 (2)	0.000 (2)	−0.0144 (19)	0.012 (2)
C10	0.065 (3)	0.078 (3)	0.0364 (18)	−0.003 (2)	0.0001 (18)	−0.009 (2)
C11	0.065 (3)	0.084 (3)	0.050 (2)	0.017 (3)	−0.0014 (18)	−0.017 (2)
C12	0.045 (2)	0.061 (2)	0.0468 (19)	0.012 (2)	−0.0053 (16)	−0.0020 (19)

Geometric parameters (Å, º) top

S1—O2	1.429 (2)	C4—H4	0.9300
S1—O1	1.430 (3)	C5—C6	1.372 (4)
S1—N1	1.622 (3)	C5—H5	0.9300
S1—C7	1.769 (3)	C7—C8	1.371 (5)
N1—C6	1.445 (4)	C7—C12	1.375 (5)
N1—H1N	0.9629	C8—C9	1.381 (5)
C1—C6	1.371 (5)	C8—H8	0.9300
C1—C2	1.380 (5)	C9—C10	1.371 (6)
C1—H1	0.9300	C9—H9	0.9300
C2—C3	1.380 (4)	C10—C11	1.355 (6)
C2—H2	0.9300	C10—H10	0.9300
O3—C3	1.365 (4)	C11—C12	1.381 (5)
O3—H3	0.8200	C11—H11	0.9300
C3—C4	1.370 (5)	C12—H12	0.9300
C4—C5	1.381 (5)

O2—S1—O1	120.06 (15)	C6—C5—H5	119.8
O2—S1—N1	107.82 (15)	C4—C5—H5	119.8
O1—S1—N1	105.73 (15)	C1—C6—C5	119.7 (3)
O2—S1—C7	107.28 (15)	C1—C6—N1	121.3 (3)
O1—S1—C7	107.48 (16)	C5—C6—N1	119.0 (3)
N1—S1—C7	107.99 (15)	C8—C7—C12	120.8 (3)
C6—N1—S1	119.2 (2)	C8—C7—S1	119.9 (3)
C6—N1—H1N	116.4	C12—C7—S1	119.3 (3)
S1—N1—H1N	107.6	C7—C8—C9	119.0 (4)
C6—C1—C2	120.4 (3)	C7—C8—H8	120.5
C6—C1—H1	119.8	C9—C8—H8	120.5
C2—C1—H1	119.8	C10—C9—C8	120.2 (4)
C1—C2—C3	119.6 (3)	C10—C9—H9	119.9
C1—C2—H2	120.2	C8—C9—H9	119.9
C3—C2—H2	120.2	C11—C10—C9	120.5 (4)
C3—O3—H3	109.5	C11—C10—H10	119.7
O3—C3—C4	116.8 (3)	C9—C10—H10	119.7
O3—C3—C2	123.1 (3)	C10—C11—C12	120.2 (4)
C4—C3—C2	120.1 (3)	C10—C11—H11	119.9
C3—C4—C5	119.8 (3)	C12—C11—H11	119.9
C3—C4—H4	120.1	C7—C12—C11	119.3 (3)
C5—C4—H4	120.1	C7—C12—H12	120.3
C6—C5—C4	120.4 (3)	C11—C12—H12	120.3

O2—S1—N1—C6	−45.9 (3)	O2—S1—C7—C8	−152.9 (3)
O1—S1—N1—C6	−175.5 (2)	O1—S1—C7—C8	−22.5 (3)
C7—S1—N1—C6	69.7 (3)	N1—S1—C7—C8	91.1 (3)
C6—C1—C2—C3	−2.0 (5)	O2—S1—C7—C12	28.9 (3)
C1—C2—C3—O3	−177.7 (3)	O1—S1—C7—C12	159.3 (3)
C1—C2—C3—C4	1.8 (5)	N1—S1—C7—C12	−87.1 (3)
O3—C3—C4—C5	179.1 (3)	C12—C7—C8—C9	−0.9 (6)
C2—C3—C4—C5	−0.4 (5)	S1—C7—C8—C9	−179.1 (3)
C3—C4—C5—C6	−0.9 (5)	C7—C8—C9—C10	0.4 (6)
C2—C1—C6—C5	0.7 (5)	C8—C9—C10—C11	0.3 (6)
C2—C1—C6—N1	−179.4 (3)	C9—C10—C11—C12	−0.6 (7)
C4—C5—C6—C1	0.8 (5)	C8—C7—C12—C11	0.6 (5)
C4—C5—C6—N1	−179.2 (3)	S1—C7—C12—C11	178.8 (3)
S1—N1—C6—C1	−101.5 (3)	C10—C11—C12—C7	0.2 (6)
S1—N1—C6—C5	78.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.96	2.07	3.030 (3)	173
O3—H3···O1ⁱⁱ	0.82	2.05	2.857 (4)	166

Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₁NO₃S
M_r	249.28
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	5.1072 (2), 9.3948 (4), 24.0903 (10)
V (Å³)	1155.88 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.12 × 0.12 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6402, 2808, 2076
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.146, 1.02
No. of reflections	2808
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.26
Absolute structure	Flack (1983), 1118 Friedel pairs
Absolute structure parameter	0.08 (13)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2006), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.96	2.07	3.030 (3)	173.0
O3—H3···O1ⁱⁱ	0.82	2.05	2.857 (4)	166.0

Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z.

Acknowledgements

The authors are grateful to the Higher Education Commission of Pakistan for financial support to purchase the diffractometer.

References

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