Literature DB >> 21589184

N-(2-Hy-droxy-1,1-dimethyl-eth-yl)-benzene-sulfonamide.

Nadia Abbas, Mehmet Akkurt, Muhammad Athar Abbasi, Shahzad Sharif, Islam Ullah Khan.   

Abstract

In the title mol-ecule, C(10)H(15)NO(3)S, the S atom is bonded in a distorted tetra-hedral geometry. In the crystal structure, inter-molecular N-H⋯O, O-H⋯O and weak C-H⋯O hydrogen bonds connect the mol-ecules to form a two-dimensional network parallel to (100). The 2-methyl-propan-1-ol group is disordered over two orientations with occupancies of 0.570 (3) and 0.430 (3).

Entities:  

Year:  2010        PMID： 21589184      PMCID： PMC3009078          DOI： 10.1107/S1600536810044144

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

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

Experimental

Crystal data

C10H15NO3S M = 229.30 Monoclinic, 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 ▶); 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON. 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
C10H15NO3SF(000) = 488
Mr = 229.30Dx = 1.307 Mg m−3
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 mm−1
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
Bruker APEXII CCD diffractometer2331 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.024
graphiteθmax = 28.3°, θmin = 3.4°
φ and ω scansh = −16→16
10723 measured reflectionsk = −12→10
2857 independent reflectionsl = −13→11
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 Å−3
8 restraintsΔρmin = −0.33 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.
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)
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)
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)
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
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1A⋯O3Bi0.862.142.840 (9)139
O3B—H3B⋯O2ii0.822.022.777 (10)152
C10B—H10D⋯O1iii0.972.543.478 (3)162

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

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5.  Synthesis, characterization and antimicrobial activity of new aliphatic sulfonamide.

Authors:  Neslihan Ozbek; Hikmet Katircioğlu; Nurcan Karacan; Tülay Baykal
Journal:  Bioorg Med Chem       Date:  2007-05-18       Impact factor: 3.641

6.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
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1.  N-(2-Hy-droxy-1,1-dimethyl-eth-yl)-4-methyl-benzene-sulfonamide.

Authors:  Amina Yasin; Mehmet Akkurt; Nadia Abbas; Muhammad Athar Abbasi; Islam Ullah Khan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-01-08
  1 in total

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