Literature DB >> 22219906

N-{4-[(3-Methyl-phen-yl)sulfamo-yl]phen-yl}benzamide.

Manu Lahtinen, Jyothi Damodara, Poornima Upadhyaya, Erkki Kolehmainen.   

Abstract

In the title compound, C(20)H(18)N(2)O(3)S, the dihedral angle between the central benzene ring and the amide group is 24.1 (3)° and that between this ring and the aromatic ring of the tolyl group is 68.2 (16)°. In the crystal, adjacent mol-ecules are linked by N-H⋯O hydrogen bonds into a linear chain running along [100]. Weak C-H⋯O contacts also occur. Extensive weak π-π inter-actions exist from both face-to-face and face-to-edge inter-actions occur between the aromatic rings [centroid-centroid distances = 3.612 (2) and 4.843 (2) Å].

Entities:  

Year:  2011        PMID： 22219906      PMCID： PMC3247601          DOI： 10.1107/S1600536811040384

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


Related literature

For related structures, see: Aziz-ur-Rehman et al. (2010a ▶,b ▶,c ▶); Khan et al. (2010 ▶); Shad et al. (2008 ▶, 2009 ▶); Yasmeen et al. (2010 ▶); Gowda et al. (2007 ▶).

Experimental

Crystal data

C20H18N2O3S M = 366.42 Triclinic, a = 8.5344 (2) Å b = 8.8477 (3) Å c = 12.4383 (4) Å α = 77.924 (2)° β = 75.382 (2)° γ = 86.537 (2)° V = 888.67 (5) Å3 Z = 2 Mo Kα radiation μ = 0.21 mm−1 T = 123 K 0.32 × 0.20 × 0.16 mm

Data collection

Nonius KappaCCD diffractometer with Bruker APEXII detector Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.675, T max = 0.746 11971 measured reflections 3122 independent reflections 2591 reflections with I > 2σ(I) R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.037 wR(F 2) = 0.088 S = 1.04 3122 reflections 242 parameters 2 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.22 e Å−3 Δρmin = −0.41 e Å−3 Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶; Otwinowski et al. 2003 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006) ▶; software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811040384/ng5238sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040384/ng5238Isup4.hkl Supplementary material file. DOI: 10.1107/S1600536811040384/ng5238Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C20H18N2O3SZ = 2
Mr = 366.42F(000) = 384
Triclinic, P1Dx = 1.369 Mg m−3
a = 8.5344 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.8477 (3) ÅCell parameters from 4151 reflections
c = 12.4383 (4) Åθ = 0.4–28.3°
α = 77.924 (2)°µ = 0.21 mm−1
β = 75.382 (2)°T = 123 K
γ = 86.537 (2)°Block, colourless
V = 888.67 (5) Å30.32 × 0.20 × 0.16 mm
Nonius KappaCCD diffractometer with Bruker APEXII detector3122 independent reflections
Radiation source: fine-focus sealed tube2591 reflections with I > 2σ(I)
graphiteRint = 0.040
φ and ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.675, Tmax = 0.746k = −10→10
11971 measured reflectionsl = −14→14
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.0225P)2 + 0.7958P] where P = (Fo2 + 2Fc2)/3
3122 reflections(Δ/σ)max = 0.001
242 parametersΔρmax = 0.22 e Å−3
2 restraintsΔρmin = −0.41 e Å−3
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 2σ(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.
xyzUiso*/Ueq
C28−0.6233 (2)0.8118 (2)1.16798 (16)0.0171 (4)
C29−0.6766 (2)0.6615 (2)1.21654 (17)0.0204 (4)
H29−0.60330.57691.20930.024*
C30−0.8372 (2)0.6356 (3)1.27566 (18)0.0246 (5)
H30−0.87360.53331.30980.030*
C31−0.9443 (2)0.7590 (3)1.28473 (17)0.0257 (5)
H31−1.05490.74071.32290.031*
C32−0.8910 (2)0.9090 (3)1.23850 (18)0.0260 (5)
H32−0.96460.99331.24580.031*
C33−0.7305 (2)0.9358 (2)1.18166 (17)0.0204 (4)
H33−0.69321.03871.15190.025*
C26−0.4514 (2)0.8461 (2)1.10486 (16)0.0167 (4)
C22−0.2076 (2)0.7276 (2)0.99572 (16)0.0152 (4)
C23−0.0888 (2)0.7983 (2)1.02747 (17)0.0180 (4)
H23−0.11900.85891.08430.022*
C240.0732 (2)0.7796 (2)0.97568 (17)0.0176 (4)
H240.15450.82730.99680.021*
C190.1162 (2)0.6904 (2)0.89228 (16)0.0155 (4)
C20−0.0010 (2)0.6204 (2)0.86079 (17)0.0176 (4)
H200.02930.55950.80420.021*
C21−0.1630 (2)0.6395 (2)0.91227 (16)0.0177 (4)
H21−0.24390.59230.89040.021*
C50.3326 (2)0.9120 (2)0.65597 (16)0.0192 (4)
C60.3642 (2)1.0699 (2)0.62394 (17)0.0220 (4)
H60.41851.11680.66630.026*
C10.3176 (2)1.1604 (3)0.53119 (18)0.0276 (5)
C1B0.3540 (3)1.3306 (3)0.4984 (2)0.0390 (6)
H1B10.43561.35190.42600.058*
H1B20.39551.36170.55710.058*
H1B30.25481.38900.49090.058*
C20.2371 (3)1.0896 (3)0.47118 (19)0.0326 (6)
H20.20381.14920.40780.039*
C30.2051 (3)0.9333 (3)0.50290 (19)0.0321 (5)
H30.14920.88700.46120.039*
C40.2530 (2)0.8425 (3)0.59478 (17)0.0251 (5)
H40.23170.73470.61530.030*
N25−0.37393 (19)0.73597 (19)1.04858 (14)0.0174 (4)
N70.39203 (18)0.82946 (19)0.74938 (14)0.0172 (4)
O27−0.38543 (16)0.96655 (15)1.10373 (12)0.0208 (3)
O170.41159 (15)0.63241 (15)0.91408 (11)0.0196 (3)
O180.33106 (15)0.55489 (15)0.75619 (12)0.0204 (3)
S160.32251 (5)0.66440 (5)0.82764 (4)0.01601 (14)
H70.415 (2)0.887 (2)0.7913 (17)0.019*
H25−0.430 (2)0.668 (2)1.0390 (18)0.019*
U11U22U33U12U13U23
C280.0168 (10)0.0206 (10)0.0157 (10)0.0016 (8)−0.0056 (8)−0.0060 (8)
C290.0170 (10)0.0216 (10)0.0235 (11)0.0017 (8)−0.0045 (8)−0.0075 (9)
C300.0206 (11)0.0283 (12)0.0251 (12)−0.0053 (9)−0.0024 (9)−0.0081 (9)
C310.0157 (10)0.0428 (13)0.0197 (11)−0.0004 (9)−0.0019 (8)−0.0114 (10)
C320.0205 (11)0.0363 (13)0.0235 (12)0.0122 (9)−0.0070 (9)−0.0126 (10)
C330.0226 (10)0.0221 (10)0.0172 (10)0.0051 (8)−0.0064 (8)−0.0051 (8)
C260.0179 (10)0.0181 (10)0.0147 (10)0.0022 (8)−0.0062 (8)−0.0023 (8)
C220.0150 (9)0.0134 (9)0.0158 (10)−0.0007 (7)−0.0032 (7)0.0000 (8)
C230.0201 (10)0.0163 (10)0.0192 (10)0.0025 (8)−0.0060 (8)−0.0066 (8)
C240.0164 (10)0.0160 (10)0.0218 (11)−0.0003 (8)−0.0069 (8)−0.0044 (8)
C190.0139 (9)0.0161 (9)0.0146 (10)−0.0002 (7)−0.0017 (7)−0.0007 (8)
C200.0180 (10)0.0172 (10)0.0185 (10)−0.0002 (8)−0.0038 (8)−0.0060 (8)
C210.0164 (10)0.0169 (10)0.0215 (11)−0.0022 (8)−0.0067 (8)−0.0042 (8)
C50.0127 (9)0.0245 (11)0.0169 (10)0.0040 (8)−0.0001 (8)−0.0022 (8)
C60.0177 (10)0.0236 (11)0.0201 (11)0.0026 (8)0.0021 (8)−0.0033 (9)
C10.0200 (11)0.0306 (12)0.0227 (12)0.0089 (9)0.0048 (9)0.0012 (9)
C1B0.0414 (14)0.0288 (13)0.0329 (14)0.0107 (11)0.0030 (11)0.0064 (11)
C20.0221 (11)0.0484 (15)0.0206 (12)0.0082 (10)−0.0036 (9)0.0031 (10)
C30.0228 (11)0.0491 (15)0.0244 (12)−0.0033 (10)−0.0073 (9)−0.0048 (11)
C40.0209 (11)0.0307 (12)0.0226 (12)−0.0027 (9)−0.0044 (9)−0.0034 (9)
N250.0131 (8)0.0159 (8)0.0241 (9)−0.0008 (7)−0.0027 (7)−0.0083 (7)
N70.0161 (8)0.0172 (9)0.0190 (9)−0.0018 (7)−0.0052 (7)−0.0038 (7)
O270.0210 (7)0.0163 (7)0.0256 (8)−0.0022 (6)−0.0036 (6)−0.0073 (6)
O170.0158 (7)0.0213 (7)0.0223 (8)0.0018 (6)−0.0071 (6)−0.0032 (6)
O180.0183 (7)0.0191 (7)0.0249 (8)0.0006 (6)−0.0026 (6)−0.0100 (6)
S160.0132 (2)0.0155 (2)0.0188 (3)0.00087 (18)−0.00303 (18)−0.00364 (19)
C28—C291.392 (3)C20—C211.386 (3)
C28—C331.396 (3)C20—H200.9500
C28—C261.495 (3)C21—H210.9500
C29—C301.390 (3)C5—C41.388 (3)
C29—H290.9500C5—C61.394 (3)
C30—C311.385 (3)C5—N71.428 (3)
C30—H300.9500C6—C11.391 (3)
C31—C321.386 (3)C6—H60.9500
C31—H310.9500C1—C21.389 (3)
C32—C331.383 (3)C1—C1B1.506 (3)
C32—H320.9500C1B—H1B10.9800
C33—H330.9500C1B—H1B20.9800
C26—O271.231 (2)C1B—H1B30.9800
C26—N251.360 (2)C2—C31.380 (3)
C22—C211.390 (3)C2—H20.9500
C22—C231.400 (3)C3—C41.390 (3)
C22—N251.410 (2)C3—H30.9500
C23—C241.386 (3)C4—H40.9500
C23—H230.9500N25—H250.835 (15)
C24—C191.396 (3)N7—S161.6280 (16)
C24—H240.9500N7—H70.861 (15)
C19—C201.383 (3)O17—S161.4400 (14)
C19—S161.7642 (18)O18—S161.4328 (14)
C29—C28—C33119.77 (18)C22—C21—H21119.8
C29—C28—C26121.93 (17)C4—C5—C6119.79 (19)
C33—C28—C26118.25 (18)C4—C5—N7123.68 (18)
C30—C29—C28119.81 (18)C6—C5—N7116.48 (18)
C30—C29—H29120.1C1—C6—C5121.3 (2)
C28—C29—H29120.1C1—C6—H6119.3
C31—C30—C29120.0 (2)C5—C6—H6119.3
C31—C30—H30120.0C2—C1—C6118.3 (2)
C29—C30—H30120.0C2—C1—C1B121.6 (2)
C30—C31—C32120.40 (19)C6—C1—C1B120.1 (2)
C30—C31—H31119.8C1—C1B—H1B1109.5
C32—C31—H31119.8C1—C1B—H1B2109.5
C33—C32—C31119.89 (19)H1B1—C1B—H1B2109.5
C33—C32—H32120.1C1—C1B—H1B3109.5
C31—C32—H32120.1H1B1—C1B—H1B3109.5
C32—C33—C28120.08 (19)H1B2—C1B—H1B3109.5
C32—C33—H33120.0C3—C2—C1120.6 (2)
C28—C33—H33120.0C3—C2—H2119.7
O27—C26—N25122.61 (17)C1—C2—H2119.7
O27—C26—C28121.90 (17)C2—C3—C4121.2 (2)
N25—C26—C28115.48 (16)C2—C3—H3119.4
C21—C22—C23119.99 (17)C4—C3—H3119.4
C21—C22—N25117.37 (16)C5—C4—C3118.8 (2)
C23—C22—N25122.59 (17)C5—C4—H4120.6
C24—C23—C22119.69 (18)C3—C4—H4120.6
C24—C23—H23120.2C26—N25—C22127.54 (16)
C22—C23—H23120.2C26—N25—H25118.0 (15)
C23—C24—C19119.67 (17)C22—N25—H25114.2 (15)
C23—C24—H24120.2C5—N7—S16124.74 (13)
C19—C24—H24120.2C5—N7—H7114.5 (14)
C20—C19—C24120.72 (17)S16—N7—H7109.6 (14)
C20—C19—S16119.57 (15)O18—S16—O17118.60 (8)
C24—C19—S16119.70 (14)O18—S16—N7109.02 (8)
C19—C20—C21119.61 (18)O17—S16—N7104.61 (8)
C19—C20—H20120.2O18—S16—C19107.45 (8)
C21—C20—H20120.2O17—S16—C19108.77 (8)
C20—C21—C22120.32 (17)N7—S16—C19107.99 (8)
C20—C21—H21119.8
C33—C28—C29—C301.8 (3)C5—C6—C1—C20.6 (3)
C26—C28—C29—C30179.18 (18)C5—C6—C1—C1B−179.75 (18)
C28—C29—C30—C310.9 (3)C6—C1—C2—C3−0.3 (3)
C29—C30—C31—C32−2.2 (3)C1B—C1—C2—C3−180.0 (2)
C30—C31—C32—C330.8 (3)C1—C2—C3—C4−0.4 (3)
C31—C32—C33—C281.9 (3)C6—C5—C4—C3−0.6 (3)
C29—C28—C33—C32−3.2 (3)N7—C5—C4—C3−177.87 (18)
C26—C28—C33—C32179.34 (18)C2—C3—C4—C50.9 (3)
C29—C28—C26—O27−148.36 (19)O27—C26—N25—C229.8 (3)
C33—C28—C26—O2729.1 (3)C28—C26—N25—C22−170.63 (17)
C29—C28—C26—N2532.1 (3)C21—C22—N25—C26−158.59 (19)
C33—C28—C26—N25−150.49 (18)C23—C22—N25—C2624.1 (3)
C21—C22—C23—C24−0.3 (3)C4—C5—N7—S16−24.1 (3)
N25—C22—C23—C24177.01 (17)C6—C5—N7—S16158.56 (14)
C22—C23—C24—C190.0 (3)C5—N7—S16—O1855.80 (17)
C23—C24—C19—C200.0 (3)C5—N7—S16—O17−176.39 (15)
C23—C24—C19—S16−179.17 (14)C5—N7—S16—C19−60.64 (17)
C24—C19—C20—C210.3 (3)C20—C19—S16—O18−5.69 (18)
S16—C19—C20—C21179.41 (15)C24—C19—S16—O18173.47 (15)
C19—C20—C21—C22−0.5 (3)C20—C19—S16—O17−135.24 (15)
C23—C22—C21—C200.5 (3)C24—C19—S16—O1743.92 (18)
N25—C22—C21—C20−176.90 (17)C20—C19—S16—N7111.78 (16)
C4—C5—C6—C1−0.1 (3)C24—C19—S16—N7−69.07 (17)
N7—C5—C6—C1177.35 (17)
D—H···AD—HH···AD···AD—H···A
N7—H7···O27i0.86 (2)1.99 (2)2.813 (2)160.(2)
N25—H25···O17ii0.84 (2)2.38 (2)3.062 (2)140.(2)
C4—H4···O180.952.403.047 (3)125
C20—H20···O180.952.492.884 (2)105
C23—H23···O270.952.392.907 (2)114
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N7—H7⋯O27i0.86 (2)1.99 (2)2.813 (2)160 (2)
N25—H25⋯O17ii0.84 (2)2.38 (2)3.062 (2)140 (2)
C4—H4⋯O180.952.403.047 (3)125

Symmetry codes: (i) ; (ii) .

  8 in total

1.  Multiparametric scaling of diffraction intensities.

Authors:  Zbyszek Otwinowski; Dominika Borek; Wladyslaw Majewski; Wladek Minor
Journal:  Acta Crystallogr A       Date:  2003-04-25       Impact factor: 2.290

2.  A short history of SHELX.

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

3.  4-Methyl-N-(4-methyl-phen-yl)benzene-sulfonamide.

Authors:  Islam Ullah Khan; Shahzad Sharif; Mehmet Akkurt; Arif Sajjad; Jamil Ahmad
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-03-10

4.  N-(2-Meth-oxy-phen-yl)benzene-sulfonamide.

Authors:  Muhammad Arif Sajjad; Mehmet Akkurt; Shahzad Sharif; Muhammad Athar Abbasi; Islam Ullah Khan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-06-26

5.  N-(5-Chloro-2-meth-oxy-phen-yl)benzene-sulfonamide.

Authors:  Mehmet Akkurt; Muhammad Athar Abbasi; Islam Ullah Khan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-10-20

6.  N-Ethyl-N-(2-meth-oxy-phen-yl)benzene-sulfonamide.

Authors:  Humaira Rafique; Mehmet Akkurt; Nabila Dilber; Muhammad Athar Abbasi; Islam Ullah Khan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-06-23

7.  4-Chloro-2-[(E)-({4-[N-(3,4-dimethyl-isoxazol-5-yl)sulfamo-yl]phen-yl}iminio)meth-yl]phenolate.

Authors:  Hazoor A Shad; Zahid H Chohan; M Nawaz Tahir; Islam Ullah Khan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-02-27

8.  N-{4-[(5-Methyl-isoxazol-3-yl)sulfamo-yl]phen-yl}benzamide.

Authors:  Sumera Yasmeen; Shahzad Murtaza; Mehmet Akkurt; Islam Ullah Khan; Shahzad Sharif
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-08-11
  8 in total

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