Literature DB >> 21587982

N-{[4-(4-Meth-oxy-benzene-sulfonamido)-phen-yl]sulfon-yl}acetamide.

Ghulam Mustafa, Mehmet Akkurt, Islam Ullah Khan, Rahat Naseem, Beenish Sajjad.   

Abstract

In the title compound, C(15)H(16)N(2)O(6)S(2), the dihedral angle between the benzene rings is 83.2 (3)°. The mol-ecular conformation is stabilized by an intra-molecular C-H⋯O inter-action. In the crystal structure, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds and additional stabilization is provided by weak C-H⋯π inter-actions.

Entities:  

Year:  2010        PMID： 21587982      PMCID： PMC3006991          DOI： 10.1107/S1600536810023925

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


Related literature

For previous studies on the synthesis of sulfonamide derivatives with phenyl glycine, see: Ashfaq et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C15H16N2O6S2 M = 384.44 Monoclinic, a = 5.3651 (10) Å b = 20.551 (3) Å c = 15.034 (2) Å β = 94.040 (7)° V = 1653.5 (4) Å3 Z = 4 Mo Kα radiation μ = 0.36 mm−1 T = 296 K 0.25 × 0.08 × 0.07 mm

Data collection

Bruker Kappa APEXII CCD diffractometer 13678 measured reflections 3771 independent reflections 1608 reflections with I > 2σ(I) R int = 0.114

Refinement

R[F 2 > 2σ(F 2)] = 0.084 wR(F 2) = 0.189 S = 0.89 3771 reflections 226 parameters H-atom parameters constrained Δρmax = 0.83 e Å−3 Δρmin = −0.32 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: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023925/hb5502sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023925/hb5502Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H16N2O6S2F(000) = 800
Mr = 384.44Dx = 1.544 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1463 reflections
a = 5.3651 (10) Åθ = 2.9–20.1°
b = 20.551 (3) ŵ = 0.36 mm−1
c = 15.034 (2) ÅT = 296 K
β = 94.040 (7)°Rod, colourless
V = 1653.5 (4) Å30.25 × 0.08 × 0.07 mm
Z = 4
Bruker Kappa APEXII CCD diffractometer1608 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.114
graphiteθmax = 28.4°, θmin = 3.3°
phi and ω scansh = −7→7
13678 measured reflectionsk = −27→26
3771 independent reflectionsl = −20→20
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.084Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189H-atom parameters constrained
S = 0.89w = 1/[σ2(Fo2) + (0.068P)2] where P = (Fo2 + 2Fc2)/3
3771 reflections(Δ/σ)max < 0.001
226 parametersΔρmax = 0.83 e Å−3
0 restraintsΔρmin = −0.32 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*/Ueq
S10.3465 (3)0.17871 (7)0.68802 (9)0.0373 (5)
S20.7590 (2)0.14262 (6)1.14309 (8)0.0290 (4)
O10.7672 (11)−0.0692 (3)0.5765 (3)0.082 (2)
O20.1176 (7)0.16711 (19)0.7264 (2)0.0455 (14)
O30.3551 (7)0.2208 (2)0.6128 (2)0.0515 (16)
O40.8828 (6)0.19627 (17)1.1877 (2)0.0386 (11)
O50.5388 (6)0.11632 (18)1.1764 (2)0.0377 (11)
O60.7458 (7)0.00642 (18)1.0809 (3)0.0444 (14)
N10.5446 (8)0.2099 (2)0.7634 (2)0.0348 (14)
N20.9779 (7)0.0863 (2)1.1487 (3)0.0335 (14)
C10.4677 (10)0.1033 (3)0.6585 (3)0.0373 (19)
C20.6748 (11)0.1020 (3)0.6078 (4)0.051 (2)
C30.7658 (13)0.0438 (4)0.5824 (4)0.060 (3)
C40.6569 (12)−0.0140 (4)0.6055 (4)0.055 (2)
C50.4498 (13)−0.0129 (3)0.6561 (4)0.054 (2)
C60.3601 (11)0.0463 (3)0.6810 (4)0.0450 (19)
C70.671 (2)−0.1301 (4)0.5999 (5)0.102 (4)
C80.5896 (9)0.1915 (2)0.8531 (3)0.0274 (16)
C90.7968 (9)0.2181 (3)0.8989 (3)0.0345 (17)
C100.8521 (9)0.2034 (3)0.9879 (3)0.0353 (17)
C110.6938 (9)0.1611 (2)1.0304 (3)0.0278 (16)
C120.4918 (9)0.1342 (2)0.9844 (3)0.0322 (17)
C130.4361 (10)0.1492 (3)0.8956 (3)0.0345 (17)
C140.9434 (9)0.0225 (3)1.1177 (3)0.0310 (17)
C151.1613 (10)−0.0206 (3)1.1364 (4)0.0426 (17)
H10.633000.241800.746100.0420*
H21.123000.096901.172300.0400*
H2A0.750100.140600.591600.0610*
H30.904700.042900.548800.0720*
H50.37410−0.051300.672600.0650*
H60.220800.047500.714500.0540*
H7A0.66710−0.132700.663500.1520*
H7B0.77580−0.164000.579400.1520*
H7C0.50490−0.135000.572700.1520*
H90.900000.246200.869800.0420*
H100.991900.221201.019000.0420*
H120.390300.105401.013100.0380*
H130.296700.131100.864700.0420*
H15A1.12360−0.063201.112900.0640*
H15B1.19890−0.023501.199700.0640*
H15C1.30280−0.003201.108800.0640*
U11U22U33U12U13U23
S10.0361 (8)0.0443 (9)0.0310 (7)0.0051 (6)−0.0015 (6)0.0047 (6)
S20.0303 (7)0.0313 (7)0.0256 (6)0.0004 (5)0.0039 (5)−0.0046 (5)
O10.110 (4)0.070 (4)0.066 (3)0.033 (3)0.003 (3)−0.024 (3)
O20.032 (2)0.054 (3)0.050 (2)0.0047 (18)−0.0006 (17)−0.0042 (19)
O30.061 (3)0.058 (3)0.034 (2)0.008 (2)−0.0071 (19)0.0161 (19)
O40.045 (2)0.034 (2)0.0362 (19)−0.0048 (17)−0.0013 (17)−0.0108 (17)
O50.0298 (19)0.050 (2)0.0343 (19)0.0003 (17)0.0090 (15)−0.0001 (17)
O60.034 (2)0.035 (2)0.063 (3)−0.0026 (17)−0.0055 (18)−0.0050 (19)
N10.040 (2)0.036 (3)0.028 (2)−0.006 (2)−0.0013 (19)0.0099 (19)
N20.027 (2)0.038 (3)0.034 (2)−0.0021 (19)−0.0081 (18)0.001 (2)
C10.033 (3)0.048 (4)0.030 (3)−0.001 (3)−0.005 (2)−0.002 (2)
C20.046 (4)0.056 (4)0.050 (4)−0.010 (3)0.003 (3)−0.011 (3)
C30.050 (4)0.083 (5)0.048 (4)0.006 (4)0.010 (3)−0.018 (4)
C40.054 (4)0.067 (5)0.042 (3)0.019 (4)−0.014 (3)−0.015 (3)
C50.072 (5)0.045 (4)0.043 (3)0.007 (3)−0.010 (3)0.002 (3)
C60.048 (3)0.052 (4)0.035 (3)0.003 (3)0.004 (3)0.003 (3)
C70.189 (10)0.054 (5)0.060 (5)0.039 (6)−0.002 (6)−0.005 (4)
C80.029 (3)0.025 (3)0.028 (2)0.004 (2)0.001 (2)0.005 (2)
C90.036 (3)0.033 (3)0.035 (3)−0.014 (2)0.007 (2)0.005 (2)
C100.033 (3)0.036 (3)0.037 (3)−0.004 (2)0.003 (2)−0.004 (2)
C110.033 (3)0.026 (3)0.025 (2)0.002 (2)0.006 (2)−0.002 (2)
C120.034 (3)0.029 (3)0.033 (3)−0.009 (2)−0.001 (2)0.003 (2)
C130.031 (3)0.039 (3)0.033 (3)−0.004 (2)−0.002 (2)0.004 (2)
C140.026 (3)0.037 (3)0.030 (3)−0.004 (2)0.002 (2)0.003 (2)
C150.037 (3)0.041 (3)0.050 (3)0.013 (3)0.004 (2)−0.002 (3)
S1—O21.413 (4)C8—C131.384 (7)
S1—O31.427 (4)C8—C91.379 (7)
S1—N11.629 (4)C9—C101.383 (7)
S1—C11.750 (6)C10—C111.401 (7)
S2—O41.430 (4)C11—C121.361 (7)
S2—O51.422 (3)C12—C131.382 (6)
S2—N21.647 (4)C14—C151.478 (8)
S2—C111.747 (5)C2—H2A0.9300
O1—C41.365 (10)C3—H30.9300
O1—C71.408 (10)C5—H50.9300
O6—C141.207 (6)C6—H60.9300
N1—C81.405 (5)C7—H7A0.9600
N2—C141.399 (7)C7—H7B0.9600
N1—H10.8600C7—H7C0.9600
N2—H20.8600C9—H90.9300
C1—C61.359 (9)C10—H100.9300
C1—C21.391 (8)C12—H120.9300
C2—C31.357 (10)C13—H130.9300
C3—C41.379 (11)C15—H15A0.9600
C4—C51.390 (9)C15—H15B0.9600
C5—C61.370 (9)C15—H15C0.9600
O2—S1—O3120.2 (2)S2—C11—C12120.1 (3)
O2—S1—N1109.0 (2)C10—C11—C12120.5 (4)
O2—S1—C1107.7 (3)C11—C12—C13120.7 (4)
O3—S1—N1104.9 (2)C8—C13—C12119.4 (5)
O3—S1—C1107.6 (2)O6—C14—C15125.5 (5)
N1—S1—C1106.8 (2)N2—C14—C15114.5 (4)
O4—S2—O5119.9 (2)O6—C14—N2120.0 (5)
O4—S2—N2102.2 (2)C1—C2—H2A120.00
O4—S2—C11110.0 (2)C3—C2—H2A120.00
O5—S2—N2108.8 (2)C2—C3—H3119.00
O5—S2—C11108.0 (2)C4—C3—H3119.00
N2—S2—C11107.2 (2)C4—C5—H5121.00
C4—O1—C7119.0 (6)C6—C5—H5121.00
S1—N1—C8128.4 (3)C1—C6—H6119.00
S2—N2—C14124.4 (3)C5—C6—H6119.00
S1—N1—H1116.00O1—C7—H7A109.00
C8—N1—H1116.00O1—C7—H7B109.00
S2—N2—H2118.00O1—C7—H7C109.00
C14—N2—H2118.00H7A—C7—H7B110.00
S1—C1—C2118.8 (5)H7A—C7—H7C110.00
S1—C1—C6121.9 (4)H7B—C7—H7C110.00
C2—C1—C6119.3 (6)C8—C9—H9120.00
C1—C2—C3119.2 (6)C10—C9—H9120.00
C2—C3—C4121.4 (6)C9—C10—H10121.00
O1—C4—C5124.7 (7)C11—C10—H10121.00
C3—C4—C5119.5 (7)C11—C12—H12120.00
O1—C4—C3115.8 (6)C13—C12—H12120.00
C4—C5—C6118.3 (6)C8—C13—H13120.00
C1—C6—C5122.3 (6)C12—C13—H13120.00
C9—C8—C13120.2 (4)C14—C15—H15A109.00
N1—C8—C9116.8 (4)C14—C15—H15B109.00
N1—C8—C13123.0 (4)C14—C15—H15C109.00
C8—C9—C10120.5 (5)H15A—C15—H15B109.00
C9—C10—C11118.8 (5)H15A—C15—H15C109.00
S2—C11—C10119.4 (4)H15B—C15—H15C110.00
O2—S1—N1—C842.8 (5)S2—N2—C14—O63.0 (7)
O3—S1—N1—C8172.7 (4)S2—N2—C14—C15−175.4 (4)
C1—S1—N1—C8−73.3 (5)S1—C1—C2—C3−178.1 (5)
O2—S1—C1—C2171.0 (4)C6—C1—C2—C3−0.4 (8)
O2—S1—C1—C6−6.7 (5)S1—C1—C6—C5178.2 (5)
O3—S1—C1—C240.0 (5)C2—C1—C6—C50.6 (9)
O3—S1—C1—C6−137.6 (5)C1—C2—C3—C40.2 (9)
N1—S1—C1—C2−72.1 (5)C2—C3—C4—O1−179.5 (6)
N1—S1—C1—C6110.2 (5)C2—C3—C4—C5−0.2 (10)
O4—S2—N2—C14176.6 (4)O1—C4—C5—C6179.6 (6)
O5—S2—N2—C1448.9 (5)C3—C4—C5—C60.3 (9)
C11—S2—N2—C14−67.7 (4)C4—C5—C6—C1−0.5 (9)
O4—S2—C11—C1030.0 (5)N1—C8—C9—C10178.9 (5)
O4—S2—C11—C12−150.4 (4)C13—C8—C9—C10−0.7 (8)
O5—S2—C11—C10162.5 (4)N1—C8—C13—C12−179.2 (4)
O5—S2—C11—C12−17.9 (4)C9—C8—C13—C120.4 (8)
N2—S2—C11—C10−80.4 (4)C8—C9—C10—C110.0 (8)
N2—S2—C11—C1299.2 (4)C9—C10—C11—S2−179.4 (4)
C7—O1—C4—C3178.1 (6)C9—C10—C11—C121.1 (8)
C7—O1—C4—C5−1.2 (9)S2—C11—C12—C13179.0 (4)
S1—N1—C8—C9169.1 (4)C10—C11—C12—C13−1.4 (7)
S1—N1—C8—C13−11.4 (7)C11—C12—C13—C80.7 (8)
Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.862.092.932 (5)168
N2—H2···O5ii0.862.263.071 (5)157
C13—H13···O20.932.352.986 (6)126
C15—H15C···O6ii0.962.453.348 (7)156
C15—H15B···Cg1iii0.962.793.722 (6)164
C15—H15A···Cg2iii0.962.793.589 (6)141
Table 1

Hydrogen-bond geometry (Å, °)

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

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1⋯O4i0.862.092.932 (5)168
N2—H2⋯O5ii0.862.263.071 (5)157
C13—H13⋯O20.932.352.986 (6)126
C15—H15C⋯O6ii0.962.453.348 (7)156
C15—H15B⋯Cg1iii0.962.793.722 (6)164
C15—H15A⋯Cg2iii0.962.793.589 (6)141

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

  3 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  N-[4-(p-Toluenesulfonamido)phen-ylsulfon-yl]acetamide.

Authors:  Muhammad Ashfaq; Islam Ullah Khan; Muhammad Nadeem Arshad; Hamad Ahmad; Muhammad Nadeem Asghar
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-01-09

3.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  3 in total
  5 in total

1.  4-(4-Meth-oxy-benzene-sulfonamido)-benzoic acid.

Authors:  Islam Ullah Khan; Ghulam Mustafa; Mehmet Akkurt
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-06-30

2.  Cyano-methyl 4-(4-methyl-benzene-sulfonamido)-benzoate.

Authors:  Ghulam Mustafa; Mehmet Akkurt; Islam Ullah Khan; Tahir Muhmood
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-04-21

3.  2-{4-[Acet-yl(eth-yl)amino]-benzene-sulfonamido}-benzoic acid.

Authors:  Ghulam Mustafa; Islam Ullah Khan; Farhan Mehmood Khan; Mehmet Akkurt
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-04-04

4.  Butyl 4-(4-methyl-benzene-sulfonamido)-benzoate.

Authors:  Ghulam Mustafa; Mehmet Akkurt; Yılmaz Dağdemir; Islam Ullah Khan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-04-28

5.  Propyl 2-(4-methyl-benzene-sulfonamido)-benzoate.

Authors:  Ghulam Mustafa; Tahir Muhmood; Islam Ullah Khan; Mehmet Akkurt
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-04-13
  5 in total

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