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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o3028.
Published online 2010 October 31. doi:  10.1107/S1600536810044144
PMCID: PMC3009078

N-(2-Hy­droxy-1,1-dimethyl­eth­yl)­benzene­sulfonamide

Abstract

In the title mol­ecule, C10H15NO3S, the S atom is bonded in a distorted tetra­hedral geometry. In the crystal structure, inter­molecular N—H(...)O, O—H(...)O and weak C—H(...)O hydrogen bonds connect the mol­ecules to form a two-dimensional network parallel to (100). The 2-methyl­propan-1-ol group is disordered over two orientations with occupancies of 0.570 (3) and 0.430 (3).

Related literature

For general background to sulfonamide derivatives, see: Ozbek et al. (2007 [triangle]); Parari et al. (2008 [triangle]). For our previous structural studies on sulfonamide derivatives, see: Asiri et al. (2009 [triangle]); Aziz-ur-Rehman et al. (2010 [triangle]).

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Object name is e-66-o3028-scheme1.jpg

Experimental

Crystal data

  • C10H15NO3S
  • M r = 229.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3028-efi1.jpg
  • a = 12.4094 (3) Å
  • b = 9.0042 (2) Å
  • c = 10.4525 (2) Å
  • β = 93.731 (1)°
  • V = 1165.45 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.27 mm−1
  • T = 296 K
  • 0.24 × 0.16 × 0.07 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • 10723 measured reflections
  • 2857 independent reflections
  • 2331 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.119
  • S = 1.04
  • 2857 reflections
  • 176 parameters
  • 8 restraints
  • H-atom parameters constrained
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810044144/lh5159sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044144/lh5159Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

The sulfonamide moiety is found in a number of synthetic as well as natural compounds and renders various biological acitivities in these compounds (Ozbek et al., 2007, Parari et al., 2008). In continuation of our structural studies on various sulfonamide derivatives (Asiri et al., 2009, Aziz-ur-Rehman et al., 2010) herein we report the crystal structure of the title compound (I).

The molecular structure of (I) is shown in Fig. 1 and reveals a distorted tetrahedral geometry around the S atom [maximum deviation from the ideal sp3 hybridized geometry for O—S—O = 119.29 (8)°]. There are weak intramolecular C—H···O contacts within the molecule. In the crystal structure, intermolecular N—H···O, O—H···O and weak C—H···O hydrogen bonds connect the molecules to form a two-dimensional network parallel to (100) (Fig. 2).

Experimental

A mixture of benzenesulfonyl chloride (10.0 mmol; 1.28 ml), 2-amino-2-methyl propanol (10.0 mmol; 0.95 ml), aqueous sodium carbonate (10%; 15.0 ml) and water (20 ml) was stirred for one and half hours at room temperature. The crude mixture was washed with distilled water and dried. The product was dissolved in methanol and recrystallized by slow evaporation of the solvent, to generate colourless crystals of N-(2-hydroxy-1,1-dimethylethyl)benzenesulfonamide in 65% yield.

Refinement

All H atoms were positioned geometrically with N—H = 0.86, O—H = 0.82 and C—H = 0.93–0.97 Å and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C, N) or 1.5Ueq(Cmethyl,O). The 2-methylpropan-1-ol group of the title molecule show disoder over two sets of sites with an occupancy ratio of 0.570 (3):0.430 (3).

Figures

Fig. 1.
The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level. The disorder is not shown.
Fig. 2.
Part of the crystal structure of (I) H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity and only the major component of the disorder is shown.

Crystal data

C10H15NO3SF(000) = 488
Mr = 229.30Dx = 1.307 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5041 reflections
a = 12.4094 (3) Åθ = 2.8–28.2°
b = 9.0042 (2) ŵ = 0.27 mm1
c = 10.4525 (2) ÅT = 296 K
β = 93.731 (1)°Block, colourless
V = 1165.45 (4) Å30.24 × 0.16 × 0.07 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer2331 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.024
graphiteθmax = 28.3°, θmin = 3.4°
[var phi] and ω scansh = −16→16
10723 measured reflectionsk = −12→10
2857 independent reflectionsl = −13→11

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0674P)2 + 0.1878P] where P = (Fo2 + 2Fc2)/3
2857 reflections(Δ/σ)max = 0.001
176 parametersΔρmax = 0.31 e Å3
8 restraintsΔρmin = −0.33 e Å3

Special details

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.

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

xyzUiso*/UeqOcc. (<1)
S10.81238 (3)0.43637 (4)0.53924 (3)0.0453 (1)
O10.76229 (12)0.56081 (15)0.47567 (14)0.0735 (5)
O20.88776 (11)0.34876 (16)0.47376 (13)0.0715 (5)
O3B0.9863 (5)0.7719 (10)0.7102 (11)0.0594 (14)0.570 (3)
N10.87618 (9)0.48927 (13)0.66870 (11)0.0397 (3)
C10.60374 (15)0.3406 (3)0.5338 (2)0.0764 (7)
C20.52364 (17)0.2428 (3)0.5643 (3)0.1035 (10)
C30.54859 (17)0.1204 (3)0.6369 (3)0.0838 (8)
C40.65240 (17)0.0938 (2)0.6815 (2)0.0694 (7)
C50.73310 (14)0.1902 (2)0.65250 (18)0.0581 (5)
C60.70811 (11)0.31395 (16)0.57831 (14)0.0437 (4)
C70.83869 (12)0.59545 (16)0.76557 (14)0.0444 (4)
C8B0.7250 (3)0.5962 (4)0.7901 (4)0.0746 (13)0.570 (3)
C9B0.9096 (4)0.5645 (4)0.8934 (3)0.0733 (13)0.570 (3)
C10B0.8755 (2)0.7543 (3)0.7249 (3)0.0519 (9)0.570 (3)
O3A0.9831 (10)0.7515 (14)0.7318 (14)0.085 (3)0.430 (3)
C8A0.7815 (4)0.4982 (5)0.8656 (4)0.0567 (11)0.430 (3)
C9A0.7497 (4)0.7001 (5)0.7058 (4)0.0597 (12)0.430 (3)
C10A0.9310 (3)0.6663 (4)0.8205 (3)0.0494 (11)0.430 (3)
H3B1.003000.725700.646900.0890*0.570 (3)
H40.668600.010400.731600.0830*
H50.804100.172200.682600.0700*
H8B10.682800.616900.711900.1120*0.570 (3)
H8B20.711900.671400.852300.1120*0.570 (3)
H8B30.705100.501000.822300.1120*0.570 (3)
H9B10.984600.566000.876200.1100*0.570 (3)
H10C0.836700.779800.644300.0620*0.570 (3)
H10D0.854200.824900.788600.0620*0.570 (3)
H9B20.891400.468900.926500.1100*0.570 (3)
H9B30.895800.639700.955400.1100*0.570 (3)
H10.586900.423600.483500.0920*
H1A0.939500.452200.684300.0480*
H20.452400.260600.535300.1240*
H30.494300.054400.656100.1010*
H8A10.719500.450400.824100.0850*0.430 (3)
H8A20.759100.560400.933600.0850*0.430 (3)
H8A30.831000.424300.900300.0850*0.430 (3)
H3A0.998300.698900.671400.1280*0.430 (3)
H9A10.689900.642000.671000.0890*0.430 (3)
H9A20.778500.757700.638600.0890*0.430 (3)
H9A30.725600.765400.770700.0890*0.430 (3)
H10A0.910600.729800.889900.0590*0.430 (3)
H10B0.980800.591900.856600.0590*0.430 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0485 (2)0.0503 (2)0.0378 (2)−0.0069 (2)0.0083 (2)0.0011 (1)
O10.0798 (9)0.0732 (9)0.0657 (8)−0.0128 (7)−0.0080 (7)0.0318 (7)
O20.0709 (8)0.0829 (9)0.0644 (8)−0.0190 (7)0.0321 (6)−0.0308 (7)
O3B0.053 (2)0.0512 (19)0.077 (3)−0.0173 (17)0.0263 (17)−0.0205 (18)
N10.0355 (6)0.0386 (6)0.0455 (6)0.0017 (4)0.0061 (5)−0.0065 (5)
C10.0514 (9)0.0801 (13)0.0952 (15)−0.0080 (9)−0.0131 (9)0.0279 (12)
C20.0492 (11)0.116 (2)0.142 (2)−0.0234 (12)−0.0186 (12)0.0368 (19)
C30.0632 (12)0.0812 (14)0.1073 (17)−0.0282 (11)0.0084 (11)0.0083 (13)
C40.0739 (12)0.0561 (10)0.0788 (13)−0.0114 (9)0.0095 (10)0.0117 (9)
C50.0491 (8)0.0577 (9)0.0672 (10)−0.0033 (7)0.0012 (7)0.0100 (8)
C60.0440 (7)0.0453 (7)0.0417 (7)−0.0050 (6)0.0026 (6)−0.0020 (6)
C70.0521 (8)0.0413 (7)0.0414 (7)0.0049 (6)0.0152 (6)−0.0027 (6)
C8B0.0581 (18)0.078 (2)0.092 (3)−0.0108 (17)0.0389 (18)−0.029 (2)
C9B0.102 (3)0.076 (2)0.0411 (15)−0.0045 (19)−0.0006 (16)−0.0051 (15)
C10B0.0560 (17)0.0421 (14)0.0591 (16)−0.0018 (12)0.0151 (12)−0.0096 (12)
O3A0.100 (5)0.080 (5)0.080 (5)−0.055 (4)0.040 (3)−0.042 (4)
C8A0.070 (2)0.053 (2)0.0499 (19)−0.0027 (18)0.0259 (18)0.0017 (17)
C9A0.068 (2)0.055 (2)0.056 (2)0.0252 (19)0.0035 (18)−0.0043 (17)
C10A0.0512 (19)0.056 (2)0.0415 (18)−0.0101 (15)0.0059 (14)−0.0122 (16)

Geometric parameters (Å, °)

S1—O11.4247 (14)C1—H10.9300
S1—O21.4315 (14)C2—H20.9300
S1—N11.5954 (12)C3—H30.9300
S1—C61.7677 (14)C4—H40.9300
O3A—C10A1.394 (14)C5—H50.9300
O3B—C10B1.402 (7)C8A—H8A20.9600
O3A—H3A0.8200C8A—H8A10.9600
O3B—H3B0.8200C8A—H8A30.9600
N1—C71.4890 (19)C8B—H8B10.9600
N1—H1A0.8600C8B—H8B20.9600
C1—C61.369 (2)C8B—H8B30.9600
C1—C21.381 (3)C9A—H9A30.9600
C2—C31.362 (4)C9A—H9A10.9600
C3—C41.362 (3)C9A—H9A20.9600
C4—C51.374 (3)C9B—H9B10.9600
C5—C61.381 (2)C9B—H9B20.9600
C7—C9A1.552 (5)C9B—H9B30.9600
C7—C10B1.569 (3)C10A—H10B0.9700
C7—C8A1.569 (5)C10A—H10A0.9700
C7—C8B1.450 (4)C10B—H10D0.9700
C7—C10A1.401 (4)C10B—H10C0.9700
C7—C9B1.576 (4)
S1···H8B12.9800H8A1···C62.8400
S1···H9A12.8100H1A···H3A2.3400
S1···H9A23.1100H1A···H9B12.2900
O1···C8B3.364 (4)H1A···H10B2.2300
O1···C10B3.364 (3)H1A···O3Bv2.1400
O1···C9A2.726 (4)H1A···C10Bv3.0100
O2···O3Bi2.777 (10)H1A···O3Av2.2000
O2···O3Ai2.907 (14)H1A···C10Av3.0400
O3A···N1ii2.912 (13)H1A···O3A2.7900
O3A···N12.767 (13)H2···H8B2vi2.5500
O3A···O2i2.907 (14)H8A2···H9A32.5300
O3B···N12.908 (9)H8A2···H10A2.4900
O3B···O2i2.777 (10)H3···C8Bvi2.8400
O3B···N1ii2.840 (9)H3···H8B3vi2.5500
O3B···C9Bii3.157 (10)H8A3···H10B2.4600
O1···H12.5100H8A3···O2vii2.6600
O1···H8B12.7600H3A···N12.4200
O1···H9A3iii2.6700H3A···H1A2.3400
O1···H4iv2.8100H3A···O2i2.1800
O1···H8B2iii2.7900H3B···O2i2.0200
O1···H10Aiii2.8200H3B···N12.6700
O1···H9A12.4000H4···C9Axi2.9900
O1···H10C2.7600H4···H9A3xi2.3400
O1···H10Diii2.5400H4···O1vii2.8100
O1···H9A22.4600H9A1···S12.8100
O2···H8A3iv2.6600H9A1···O12.4000
O2···H9B2iv2.9000H9A1···H8A12.3700
O2···H3Ai2.1800H5···O3Bv2.9100
O2···H3Bi2.0200H5···O3Av2.8200
O3A···H5ii2.8200H9A2···S13.1100
O3A···H9A22.6600H9A2···O12.4600
O3A···H1Aii2.2000H9A2···O3A2.6600
O3A···H1A2.7900H9A3···H4x2.3400
O3B···H9B12.5400H9A3···H8A22.5300
O3B···H1Aii2.1400H9A3···O1xii2.6700
O3B···H5ii2.9100H9A3···H10A2.5600
O3B···H9B2ii2.7900H8B1···C63.0900
O3B···H9B1ii2.8300H8B1···H10C2.5400
N1···O3Av2.912 (13)H8B1···S12.9800
N1···O3B2.908 (9)H8B1···O12.7600
N1···O3Bv2.840 (9)H8B2···H9B32.4800
N1···O3A2.767 (13)H8B2···H10D2.3700
N1···H3A2.4200H8B2···H2viii2.5500
N1···H3B2.6700H8B2···O1xii2.7900
C3···C8Bvi3.535 (4)H8B3···C63.0600
C5···C8A3.583 (5)H8B3···H3viii2.5500
C5···C8Aiv3.531 (5)H8B3···H9B22.5100
C6···C8B3.368 (4)H9B1···H1A2.2900
C6···C8A3.499 (5)H9B1···O3B2.5400
C8A···C5vii3.531 (5)H9B1···H9B2ix2.5100
C8A···C63.499 (5)H9B1···O3Bv2.8300
C8A···C53.583 (5)H9B1···C9Bix2.9100
C8B···C63.368 (4)H10A···H8A22.4900
C8B···O13.364 (4)H10A···H9A32.5600
C8B···C3viii3.535 (4)H10A···O1xii2.8200
C9A···O12.726 (4)H10B···H1A2.2300
C9B···O3Bv3.157 (10)H10B···H8A32.4600
C9B···C9Bix3.271 (6)H10C···H9B3iii2.2700
C10B···O13.364 (3)H10C···O12.7600
C5···H8A12.9600H10C···H8B12.5400
C6···H8B13.0900H10D···O1xii2.5400
C6···H8B33.0600H10D···H8B22.3700
C6···H8A12.8400H10D···H9B32.4400
C8B···H3viii2.8400H9B2···O3Bv2.7900
C9A···H4x2.9900H9B2···H8B32.5100
C9B···H9B2ix3.0200H9B2···C9Bix3.0200
C9B···H9B1ix2.9100H9B2···H9B1ix2.5100
C10A···H1Aii3.0400H9B2···O2vii2.9000
C10B···H1Aii3.0100H9B3···H8B22.4800
C10B···H9B3iii3.0000H9B3···H10D2.4400
H1···O12.5100H9B3···C10Bxii3.0000
H8A1···C52.9600H9B3···H10Cxii2.2700
H8A1···H9A12.3700
O1—S1—O2119.29 (8)C5—C4—H4120.00
O1—S1—N1109.76 (7)C3—C4—H4120.00
O1—S1—C6107.13 (8)C4—C5—H5120.00
O2—S1—N1105.45 (7)C6—C5—H5120.00
O2—S1—C6106.13 (8)H8A1—C8A—H8A3110.00
N1—S1—C6108.70 (7)H8A2—C8A—H8A3109.00
C10A—O3A—H3A109.00C7—C8A—H8A1109.00
C10B—O3B—H3B109.00C7—C8A—H8A2109.00
S1—N1—C7127.50 (10)C7—C8A—H8A3109.00
S1—N1—H1A116.00H8A1—C8A—H8A2110.00
C7—N1—H1A116.00C7—C8B—H8B1109.00
C2—C1—C6119.3 (2)C7—C8B—H8B2109.00
C1—C2—C3120.2 (2)H8B1—C8B—H8B3109.00
C2—C3—C4120.6 (2)C7—C8B—H8B3109.00
C3—C4—C5120.0 (2)H8B1—C8B—H8B2109.00
C4—C5—C6119.56 (16)H8B2—C8B—H8B3110.00
S1—C6—C1120.19 (14)C7—C9A—H9A1110.00
S1—C6—C5119.46 (11)H9A2—C9A—H9A3110.00
C1—C6—C5120.35 (16)C7—C9A—H9A3109.00
N1—C7—C10B106.97 (15)H9A1—C9A—H9A2109.00
N1—C7—C10A106.72 (18)C7—C9A—H9A2109.00
N1—C7—C8A105.65 (19)H9A1—C9A—H9A3109.00
N1—C7—C9A111.21 (19)C7—C9B—H9B2109.00
C9B—C7—C10B103.6 (2)C7—C9B—H9B3109.00
C8A—C7—C9A105.5 (3)C7—C9B—H9B1109.00
C8A—C7—C10A112.0 (2)H9B1—C9B—H9B3110.00
C9A—C7—C10A115.5 (2)H9B2—C9B—H9B3109.00
N1—C7—C8B118.28 (19)H9B1—C9B—H9B2110.00
C8B—C7—C9B110.3 (3)C7—C10A—H10A109.00
C8B—C7—C10B110.33 (19)C7—C10A—H10B109.00
N1—C7—C9B106.32 (17)H10A—C10A—H10B108.00
O3A—C10A—C7112.3 (6)O3A—C10A—H10A109.00
O3B—C10B—C7116.0 (4)O3A—C10A—H10B109.00
C2—C1—H1120.00O3B—C10B—H10D108.00
C6—C1—H1120.00H10C—C10B—H10D107.00
C3—C2—H2120.00C7—C10B—H10C108.00
C1—C2—H2120.00C7—C10B—H10D108.00
C2—C3—H3120.00O3B—C10B—H10C108.00
C4—C3—H3120.00
O1—S1—N1—C743.70 (14)C2—C1—C6—C50.3 (3)
O2—S1—N1—C7173.39 (12)C2—C1—C6—S1179.33 (19)
C6—S1—N1—C7−73.17 (13)C6—C1—C2—C3−0.6 (4)
N1—S1—C6—C1126.00 (15)C1—C2—C3—C40.8 (4)
O1—S1—C6—C17.45 (17)C2—C3—C4—C5−0.5 (4)
O2—S1—C6—C1−121.01 (15)C3—C4—C5—C60.2 (3)
N1—S1—C6—C5−54.93 (15)C4—C5—C6—C10.0 (3)
O1—S1—C6—C5−173.48 (13)C4—C5—C6—S1−179.10 (14)
O2—S1—C6—C558.06 (15)N1—C7—C10B—O3B−56.0 (6)
S1—N1—C7—C9B159.68 (18)C8B—C7—C10B—O3B174.2 (6)
S1—N1—C7—C8B35.1 (2)C9B—C7—C10B—O3B56.1 (6)
S1—N1—C7—C10B−90.15 (16)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, y+1/2, −z+3/2; (iii) x, −y+3/2, z−1/2; (iv) x, −y+1/2, z−1/2; (v) −x+2, y−1/2, −z+3/2; (vi) −x+1, y−1/2, −z+3/2; (vii) x, −y+1/2, z+1/2; (viii) −x+1, y+1/2, −z+3/2; (ix) −x+2, −y+1, −z+2; (x) x, y+1, z; (xi) x, y−1, z; (xii) x, −y+3/2, z+1/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O3Bv0.862.142.840 (9)139
O3B—H3B···O2i0.822.022.777 (10)152
C1—H1···O10.932.512.886 (3)105
C9B—H9B1···O3B0.962.542.881 (11)101
C10B—H10D···O1xii0.972.543.478 (3)162

Symmetry codes: (v) −x+2, y−1/2, −z+3/2; (i) −x+2, −y+1, −z+1; (xii) x, −y+3/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5159).

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