Literature DB >> 21588432

2-Benzoyl-2H-1,4-benzothia-zin-3(4H)-one.

Durre Shahwar, M Nawaz Tahir, Naeem Ahmad, Muhammad Asam Raza, Muhammad Akmal Khan.   

Abstract

In the title compound, C(15)H(11)NO(2)S, the dihedral angle between the aromatic rings is 80.35 (7)°. The heterocyclic six-membered ring is not planar: the puckering parameters of this ring are Q = 0.5308 (15) Å, θ = 63.11 (18) and ϕ = 23.5 (2)°. The mol-ecules are linked into inversion dimers with R(2) (2)(8) ring motifs by pairs of N-H⋯O hydrogen bonds. The dimers are inter-linked into polymeric sheets extending parallel to the bc plane by C-H⋯O hydrogen bonds, generating R(2) (1)(7) ring motifs. π-π inter-actions occur between the benzoyl phenyl rings with centroid-centroid separations of 3.9187 (15) Å.

Entities:  

Year:  2010        PMID： 21588432      PMCID： PMC3007413          DOI： 10.1107/S1600536810029582

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


Related literature

For puckering parameters, see: Cremer & Pople (1975 ▶). For the synthesis and anti­microbial activity of benzimidazole derivatives, see: Güven et al. (2007 ▶): Nofal et al. (2002 ▶). For related structures, see: Beryozkina et al. (2004 ▶): Kumaradhas & Nirmala (1997 ▶): Zhang et al. (2008 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H11NO2S M = 269.31 Monoclinic, a = 9.1323 (3) Å b = 15.2893 (4) Å c = 10.5214 (4) Å β = 114.669 (1)° V = 1334.99 (8) Å3 Z = 4 Mo Kα radiation μ = 0.24 mm−1 T = 296 K 0.25 × 0.20 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.939, T max = 0.950 10387 measured reflections 2399 independent reflections 2064 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.103 S = 1.04 2399 reflections 172 parameters H-atom parameters constrained Δρmax = 0.29 e Å−3 Δρmin = −0.41 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810029582/si2280sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029582/si2280Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H11NO2SF(000) = 560
Mr = 269.31Dx = 1.340 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2064 reflections
a = 9.1323 (3) Åθ = 3.4–25.3°
b = 15.2893 (4) ŵ = 0.24 mm−1
c = 10.5214 (4) ÅT = 296 K
β = 114.669 (1)°Plate, light yellow
V = 1334.99 (8) Å30.25 × 0.20 × 0.10 mm
Z = 4
Bruker Kappa APEXII CCD diffractometer2399 independent reflections
Radiation source: fine-focus sealed tube2064 reflections with I > 2σ(I)
graphiteRint = 0.023
Detector resolution: 8.10 pixels mm-1θmax = 25.3°, θmin = 3.4°
ω scansh = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −18→18
Tmin = 0.939, Tmax = 0.950l = −12→12
10387 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.046P)2 + 0.5415P] where P = (Fo2 + 2Fc2)/3
2399 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.29 e Å−3
0 restraintsΔρmin = −0.41 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 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.
xyzUiso*/Ueq
S1−0.02233 (6)0.25059 (3)0.25961 (5)0.0528 (2)
O10.07429 (16)0.26350 (9)0.61431 (13)0.0569 (4)
O2−0.15131 (15)0.08259 (8)0.46234 (17)0.0603 (5)
N10.08715 (16)0.09439 (9)0.45062 (15)0.0419 (4)
C1−0.1244 (2)0.36835 (10)0.49255 (17)0.0399 (5)
C2−0.2555 (2)0.39269 (12)0.3713 (2)0.0508 (6)
C3−0.3331 (3)0.47100 (14)0.3657 (3)0.0720 (8)
C4−0.2798 (3)0.52592 (15)0.4793 (3)0.0827 (10)
C5−0.1488 (3)0.50307 (15)0.5989 (3)0.0795 (9)
C6−0.0712 (3)0.42488 (13)0.6065 (2)0.0584 (7)
C7−0.04028 (19)0.28361 (10)0.50775 (16)0.0372 (5)
C8−0.09851 (19)0.21947 (10)0.38628 (16)0.0365 (5)
C9−0.05515 (19)0.12647 (10)0.43619 (18)0.0401 (5)
C100.2099 (2)0.13817 (11)0.42926 (18)0.0402 (5)
C110.1776 (2)0.21359 (12)0.34898 (19)0.0470 (6)
C120.3019 (3)0.25556 (14)0.3316 (3)0.0678 (9)
C130.4547 (3)0.22130 (18)0.3895 (3)0.0782 (10)
C140.4862 (3)0.14499 (16)0.4662 (3)0.0672 (8)
C150.3646 (2)0.10353 (13)0.4873 (2)0.0505 (6)
H10.105550.040560.476000.0503*
H2−0.291160.356140.293590.0609*
H3−0.421860.486630.284660.0864*
H4−0.332520.578600.475070.0992*
H5−0.112110.540720.675290.0952*
H60.017090.409710.688260.0701*
H8−0.216320.223310.340390.0439*
H120.281950.307240.280490.0813*
H130.537680.249770.376890.0939*
H140.589650.121590.503660.0807*
H150.385780.052520.540100.0606*
U11U22U33U12U13U23
S10.0689 (4)0.0489 (3)0.0425 (3)0.0067 (2)0.0251 (2)0.0100 (2)
O10.0513 (8)0.0588 (8)0.0406 (7)0.0149 (6)−0.0005 (6)−0.0002 (6)
O20.0459 (7)0.0373 (7)0.1062 (12)0.0049 (6)0.0402 (8)0.0184 (7)
N10.0378 (7)0.0277 (7)0.0595 (9)0.0014 (6)0.0196 (7)0.0057 (6)
C10.0436 (9)0.0314 (8)0.0425 (9)−0.0020 (7)0.0157 (7)0.0031 (7)
C20.0540 (11)0.0365 (9)0.0502 (10)0.0051 (8)0.0103 (9)0.0046 (8)
C30.0762 (15)0.0488 (12)0.0743 (14)0.0220 (11)0.0149 (12)0.0147 (11)
C40.112 (2)0.0438 (12)0.0907 (18)0.0277 (13)0.0407 (16)0.0041 (12)
C50.114 (2)0.0478 (12)0.0713 (15)0.0101 (13)0.0334 (14)−0.0125 (11)
C60.0721 (13)0.0466 (11)0.0477 (10)0.0033 (10)0.0163 (10)−0.0022 (8)
C70.0359 (9)0.0358 (9)0.0365 (8)−0.0010 (7)0.0119 (7)0.0046 (7)
C80.0334 (8)0.0314 (8)0.0388 (8)0.0014 (6)0.0092 (7)0.0035 (6)
C90.0354 (9)0.0310 (8)0.0513 (10)−0.0004 (7)0.0154 (7)0.0032 (7)
C100.0412 (9)0.0362 (9)0.0468 (9)−0.0054 (7)0.0220 (7)−0.0101 (7)
C110.0581 (11)0.0420 (10)0.0508 (10)−0.0057 (8)0.0326 (9)−0.0062 (8)
C120.0860 (17)0.0564 (13)0.0891 (16)−0.0114 (11)0.0645 (14)−0.0042 (11)
C130.0770 (16)0.0757 (16)0.113 (2)−0.0253 (13)0.0704 (16)−0.0254 (15)
C140.0474 (11)0.0784 (16)0.0876 (16)−0.0081 (10)0.0398 (11)−0.0316 (13)
C150.0437 (10)0.0492 (10)0.0607 (11)0.0002 (8)0.0239 (9)−0.0144 (9)
S1—C81.8057 (18)C10—C151.389 (3)
S1—C111.762 (2)C10—C111.386 (2)
O1—C71.211 (2)C11—C121.381 (3)
O2—C91.224 (2)C12—C131.372 (4)
N1—C91.337 (2)C13—C141.379 (4)
N1—C101.402 (2)C14—C151.375 (4)
N1—H10.8600C2—H20.9300
C1—C61.391 (3)C3—H30.9300
C1—C71.481 (2)C4—H40.9300
C1—C21.387 (3)C5—H50.9300
C2—C31.380 (3)C6—H60.9300
C3—C41.373 (4)C8—H80.9800
C4—C51.371 (4)C12—H120.9300
C5—C61.375 (3)C13—H130.9300
C7—C81.520 (2)C14—H140.9300
C8—C91.510 (2)C15—H150.9300
S1···O13.4635 (14)C11···O13.386 (2)
S1···N13.0108 (15)C14···S1ii3.505 (3)
S1···C23.567 (2)C15···S1ii3.432 (2)
S1···C15i3.432 (2)C2···H82.6500
S1···O1i3.3545 (16)C2···H13iv2.9000
S1···C14i3.505 (3)C8···H22.6400
S1···H23.0800C9···H1iii2.8200
O1···S13.4635 (14)C9···H3v3.1000
O1···N13.136 (2)H1···H152.3700
O1···C103.318 (2)H1···O2iii1.9800
O1···C113.386 (2)H1···C9iii2.8200
O1···S1ii3.3545 (16)H1···H1iii2.5100
O1···C8ii3.170 (2)H2···S13.0800
O2···N1iii2.8383 (19)H2···C82.6400
O1···H62.4900H2···H82.1300
O1···H8ii2.3600H2···O1i2.5500
O1···H2ii2.5500H3···N1vi2.8300
O2···H14iv2.6500H3···C9vi3.1000
O2···H1iii1.9800H6···O12.4900
N1···S13.0108 (15)H8···C22.6500
N1···O13.136 (2)H8···H22.1300
N1···O2iii2.8383 (19)H8···H13iv2.4700
N1···H3v2.8300H8···O1i2.3600
C2···S13.567 (2)H13···C2vii2.9000
C7···C103.524 (3)H13···H8vii2.4700
C8···O1i3.170 (2)H14···O2vii2.6500
C10···O13.318 (2)H15···H12.3700
C10···C73.524 (3)
C8—S1—C1198.87 (9)S1—C11—C12120.40 (16)
C9—N1—C10127.66 (14)C11—C12—C13120.2 (2)
C10—N1—H1116.00C12—C13—C14120.5 (3)
C9—N1—H1116.00C13—C14—C15120.0 (3)
C2—C1—C7122.95 (15)C10—C15—C14119.7 (2)
C2—C1—C6118.88 (17)C1—C2—H2120.00
C6—C1—C7118.16 (16)C3—C2—H2120.00
C1—C2—C3120.18 (19)C2—C3—H3120.00
C2—C3—C4120.3 (2)C4—C3—H3120.00
C3—C4—C5120.0 (2)C3—C4—H4120.00
C4—C5—C6120.4 (2)C5—C4—H4120.00
C1—C6—C5120.3 (2)C4—C5—H5120.00
O1—C7—C1122.07 (15)C6—C5—H5120.00
O1—C7—C8118.58 (15)C1—C6—H6120.00
C1—C7—C8119.35 (14)C5—C6—H6120.00
S1—C8—C7110.07 (12)S1—C8—H8108.00
C7—C8—C9111.48 (13)C7—C8—H8108.00
S1—C8—C9112.26 (12)C9—C8—H8108.00
O2—C9—C8119.05 (16)C11—C12—H12120.00
N1—C9—C8119.09 (15)C13—C12—H12120.00
O2—C9—N1121.86 (15)C12—C13—H13120.00
C11—C10—C15120.25 (18)C14—C13—H13120.00
N1—C10—C11120.91 (17)C13—C14—H14120.00
N1—C10—C15118.82 (16)C15—C14—H14120.00
C10—C11—C12119.31 (19)C10—C15—H15120.00
S1—C11—C10120.12 (15)C14—C15—H15120.00
C11—S1—C8—C776.58 (13)O1—C7—C8—S1−99.48 (17)
C11—S1—C8—C9−48.23 (14)O1—C7—C8—C925.8 (2)
C8—S1—C11—C1035.41 (16)C1—C7—C8—S180.43 (18)
C8—S1—C11—C12−149.38 (18)C1—C7—C8—C9−154.32 (16)
C10—N1—C9—O2−177.54 (17)S1—C8—C9—O2−144.64 (15)
C10—N1—C9—C82.4 (3)S1—C8—C9—N135.38 (19)
C9—N1—C10—C11−20.1 (3)C7—C8—C9—O291.3 (2)
C9—N1—C10—C15161.39 (17)C7—C8—C9—N1−88.65 (19)
C6—C1—C2—C3−1.3 (3)N1—C10—C11—S1−5.5 (2)
C7—C1—C2—C3177.2 (2)N1—C10—C11—C12179.22 (19)
C2—C1—C6—C50.7 (3)C15—C10—C11—S1172.94 (14)
C7—C1—C6—C5−177.9 (2)C15—C10—C11—C12−2.3 (3)
C2—C1—C7—O1179.82 (18)N1—C10—C15—C14179.28 (19)
C2—C1—C7—C8−0.1 (3)C11—C10—C15—C140.8 (3)
C6—C1—C7—O1−1.7 (3)S1—C11—C12—C13−173.2 (2)
C6—C1—C7—C8178.41 (19)C10—C11—C12—C132.1 (3)
C1—C2—C3—C40.9 (4)C11—C12—C13—C14−0.4 (4)
C2—C3—C4—C50.1 (4)C12—C13—C14—C15−1.2 (4)
C3—C4—C5—C6−0.7 (4)C13—C14—C15—C101.0 (4)
C4—C5—C6—C10.3 (4)
D—H···AD—HH···AD···AD—H···A
N1—H1···O2iii0.861.982.8383 (19)179
C2—H2···O1i0.932.553.453 (2)165
C8—H8···O1i0.982.363.170 (2)140
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1⋯O2i0.861.982.8383 (19)179
C2—H2⋯O1ii0.932.553.453 (2)165
C8—H8⋯O1ii0.982.363.170 (2)140

Symmetry codes: (i) ; (ii) .

  5 in total

1.  A short history of SHELX.

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2.  Synthesis, antimicrobial and molluscicidal activities of new benzimidazole derivatives.

Authors:  Z M Nofal; H H Fahmy; H S Mohamed
Journal:  Arch Pharm Res       Date:  2002-02       Impact factor: 4.946

3.  2-(4-Chloro-benzoyl-meth-yl)-2H-1,4-benzothia-zin-3(4H)-one.

Authors:  Ping Zhang; Na Du; Lan-Zhi Wang; Yuan Li
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-03-29

4.  Synthesis and antimicrobial activity of some novel phenyl and benzimidazole substituted benzyl ethers.

Authors:  Ozden Ozel Güven; Taner Erdoğan; Hakan Göker; Sulhiye Yildiz
Journal:  Bioorg Med Chem Lett       Date:  2007-01-25       Impact factor: 2.823

5.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
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