Literature DB >> 23284450

(2-(Benzo[d]thia-zol-2yl-meth-oxy)-5-chloro-phen-yl)(phen-yl)methanone.

K N Venugopala1, Susanta K Nayak, Thavendran Govender, Hendrik G Kruger, Glenn E M Maguire.   

Abstract

In the title compound, C(21)H(14)ClNO(2)S, the dihedral angle between the benzothia-zole and diphenyl methanone groups is 68.6 (2)°. The crystal structure consists of dimeric units generated by C-H⋯N bonds, further linked by C-H⋯O bonds and C-H⋯π and π-π inter-actions [centroid-centroiddistance = 3.856 (2) Å], which lead to a criss-cross assembly parallel to (001).

Entities:  

Year:  2012        PMID： 23284450      PMCID： PMC3515230          DOI： 10.1107/S1600536812041888

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


Related literature

For background to the applications of benzothia­zole derivatives, see: Rana et al. (2007 ▶); Telvekar et al. (2012 ▶); Saeed et al. (2010 ▶).

Experimental

Crystal data

C21H14ClNO2S M = 379.84 Orthorhombic, a = 7.4598 (3) Å b = 19.3131 (8) Å c = 24.4002 (9) Å V = 3515.4 (2) Å3 Z = 8 Mo Kα radiation μ = 0.35 mm−1 T = 173 K 0.22 × 0.16 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.927, T max = 0.990 52834 measured reflections 3206 independent reflections 2576 reflections with I > 2σ(I) R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.059 wR(F 2) = 0.200 S = 1.30 3206 reflections 235 parameters H-atom parameters constrained Δρmax = 0.66 e Å−3 Δρmin = −0.33 e Å−3 Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; 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 Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and PARST (Nardelli, 1995 ▶). Click here for additional data file. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812041888/bg2479sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041888/bg2479Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812041888/bg2479Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C21H14ClNO2SDx = 1.435 Mg m−3
Mr = 379.84Melting point: 403(2) K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 560 reflections
a = 7.4598 (3) Åθ = 1.7–25.3°
b = 19.3131 (8) ŵ = 0.35 mm−1
c = 24.4002 (9) ÅT = 173 K
V = 3515.4 (2) Å3Plate, colourless
Z = 80.22 × 0.16 × 0.03 mm
F(000) = 1568
Nonius KappaCCD diffractometer3206 independent reflections
Radiation source: fine-focus sealed tube2576 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
1.2° φ scans and ω scansθmax = 25.3°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)h = −8→8
Tmin = 0.927, Tmax = 0.990k = −23→23
52834 measured reflectionsl = −29→29
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.200H-atom parameters constrained
S = 1.30w = 1/[σ2(Fo2) + (0.071P)2 + 8.1626P] where P = (Fo2 + 2Fc2)/3
3206 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.66 e Å−3
0 restraintsΔρmin = −0.33 e Å−3
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S10.34601 (15)0.06802 (6)0.39552 (4)0.0309 (3)
Cl10.68528 (18)0.27003 (7)0.68940 (5)0.0470 (4)
O10.4110 (4)0.11200 (15)0.50149 (11)0.0315 (7)
N10.1614 (5)−0.02826 (17)0.44408 (14)0.0273 (8)
C60.1481 (5)−0.0405 (2)0.38812 (17)0.0270 (9)
C70.2577 (5)0.0259 (2)0.45299 (16)0.0256 (9)
C80.2953 (6)0.0542 (2)0.50881 (16)0.0276 (9)
H8A0.18250.06880.52680.033*
H8B0.35370.01870.53190.033*
O20.5685 (4)0.29934 (15)0.47346 (12)0.0373 (8)
C140.5686 (5)0.2081 (2)0.53676 (16)0.0245 (9)
C150.5962 (5)0.2376 (2)0.48050 (17)0.0258 (9)
C160.6632 (5)0.1936 (2)0.43523 (16)0.0240 (9)
C170.7650 (5)0.1344 (2)0.44537 (16)0.0266 (9)
H170.78720.12030.48200.032*
C130.6296 (5)0.2462 (2)0.58122 (17)0.0286 (9)
H130.69170.28850.57530.034*
C90.4719 (5)0.1466 (2)0.54683 (16)0.0252 (9)
C190.8018 (7)0.1161 (3)0.34894 (19)0.0400 (11)
H190.85010.08990.31950.048*
C100.4403 (6)0.1248 (2)0.60021 (17)0.0305 (9)
H100.37350.08370.60680.037*
C180.8338 (6)0.0963 (2)0.40225 (19)0.0340 (10)
H180.90360.05620.40950.041*
C110.5061 (6)0.1629 (2)0.64375 (17)0.0336 (10)
H110.48620.14770.68030.040*
C10.2398 (6)0.0070 (2)0.35491 (17)0.0286 (9)
C120.6004 (6)0.2229 (2)0.63404 (17)0.0301 (10)
C200.6980 (7)0.1747 (3)0.33833 (18)0.0409 (12)
H200.67300.18780.30160.049*
C50.0510 (6)−0.0945 (2)0.36427 (19)0.0347 (10)
H5−0.0113−0.12710.38630.042*
C40.0477 (7)−0.0993 (2)0.30759 (19)0.0407 (11)
H4−0.0177−0.13570.29070.049*
C210.6322 (6)0.2134 (2)0.38092 (18)0.0340 (10)
H210.56470.25400.37350.041*
C20.2347 (7)0.0017 (3)0.29783 (19)0.0400 (11)
H20.29610.03410.27540.048*
C30.1385 (7)−0.0517 (3)0.2751 (2)0.0442 (12)
H30.1340−0.05620.23640.053*
U11U22U33U12U13U23
S10.0343 (6)0.0302 (6)0.0282 (6)−0.0080 (5)0.0014 (4)0.0005 (4)
Cl10.0576 (8)0.0537 (8)0.0296 (6)−0.0104 (6)−0.0051 (5)−0.0114 (5)
O10.0351 (17)0.0341 (16)0.0253 (14)−0.0140 (14)0.0015 (12)−0.0025 (12)
N10.0278 (19)0.0235 (18)0.0308 (18)0.0005 (15)−0.0023 (15)0.0018 (15)
C60.023 (2)0.026 (2)0.032 (2)0.0039 (17)−0.0003 (17)−0.0032 (17)
C70.021 (2)0.025 (2)0.031 (2)0.0018 (17)0.0013 (17)0.0008 (17)
C80.028 (2)0.026 (2)0.029 (2)−0.0050 (18)0.0022 (17)0.0020 (17)
O20.051 (2)0.0240 (16)0.0366 (17)0.0032 (14)0.0062 (15)0.0024 (13)
C140.023 (2)0.024 (2)0.027 (2)0.0019 (17)0.0009 (17)−0.0010 (16)
C150.022 (2)0.025 (2)0.030 (2)−0.0031 (17)−0.0016 (17)0.0019 (17)
C160.023 (2)0.023 (2)0.026 (2)−0.0022 (17)0.0002 (16)0.0027 (17)
C170.024 (2)0.028 (2)0.027 (2)−0.0004 (18)−0.0004 (17)0.0006 (17)
C130.026 (2)0.028 (2)0.032 (2)−0.0024 (18)0.0015 (18)−0.0033 (17)
C90.023 (2)0.028 (2)0.025 (2)0.0003 (17)−0.0020 (16)−0.0040 (16)
C190.044 (3)0.043 (3)0.033 (2)−0.005 (2)0.011 (2)−0.011 (2)
C100.030 (2)0.031 (2)0.030 (2)−0.0041 (19)0.0025 (18)0.0026 (18)
C180.026 (2)0.032 (2)0.044 (3)0.0014 (18)0.0013 (19)−0.007 (2)
C110.036 (2)0.041 (3)0.024 (2)0.001 (2)0.0025 (18)0.0024 (19)
C10.025 (2)0.031 (2)0.030 (2)0.0018 (18)−0.0015 (18)−0.0024 (18)
C120.029 (2)0.035 (2)0.026 (2)0.0031 (19)−0.0021 (17)−0.0066 (18)
C200.056 (3)0.044 (3)0.023 (2)−0.005 (2)0.000 (2)0.004 (2)
C50.033 (2)0.028 (2)0.043 (3)−0.001 (2)−0.002 (2)−0.005 (2)
C40.044 (3)0.038 (3)0.040 (3)−0.004 (2)−0.008 (2)−0.014 (2)
C210.043 (3)0.029 (2)0.030 (2)−0.002 (2)−0.004 (2)0.0076 (18)
C20.046 (3)0.043 (3)0.030 (2)−0.006 (2)0.003 (2)−0.001 (2)
C30.049 (3)0.053 (3)0.031 (2)−0.004 (2)−0.002 (2)−0.008 (2)
S1—C11.731 (4)C13—H130.9500
S1—C71.750 (4)C9—C101.389 (6)
Cl1—C121.747 (4)C19—C181.377 (7)
O1—C91.370 (5)C19—C201.396 (7)
O1—C81.422 (5)C19—H190.9500
N1—C71.288 (5)C10—C111.383 (6)
N1—C61.389 (5)C10—H100.9500
C6—C51.397 (6)C18—H180.9500
C6—C11.402 (6)C11—C121.377 (6)
C7—C81.494 (6)C11—H110.9500
C8—H8A0.9900C1—C21.397 (6)
C8—H8B0.9900C20—C211.371 (6)
O2—C151.223 (5)C20—H200.9500
C14—C131.388 (6)C5—C41.386 (6)
C14—C91.411 (6)C5—H50.9500
C14—C151.500 (6)C4—C31.390 (7)
C15—C161.480 (6)C4—H40.9500
C16—C171.394 (6)C21—H210.9500
C16—C211.399 (6)C2—C31.372 (7)
C17—C181.383 (6)C2—H20.9500
C17—H170.9500C3—H30.9500
C13—C121.382 (6)
C1—S1—C788.3 (2)C20—C19—H19120.1
C9—O1—C8118.8 (3)C11—C10—C9119.9 (4)
C7—N1—C6110.1 (3)C11—C10—H10120.0
N1—C6—C5125.0 (4)C9—C10—H10120.0
N1—C6—C1115.0 (4)C19—C18—C17120.5 (4)
C5—C6—C1120.0 (4)C19—C18—H18119.8
N1—C7—C8123.8 (4)C17—C18—H18119.8
N1—C7—S1116.9 (3)C12—C11—C10119.9 (4)
C8—C7—S1119.3 (3)C12—C11—H11120.1
O1—C8—C7106.6 (3)C10—C11—H11120.1
O1—C8—H8A110.4C2—C1—C6121.0 (4)
C7—C8—H8A110.4C2—C1—S1129.3 (4)
O1—C8—H8B110.4C6—C1—S1109.7 (3)
C7—C8—H8B110.4C11—C12—C13121.0 (4)
H8A—C8—H8B108.6C11—C12—Cl1119.4 (3)
C13—C14—C9118.6 (4)C13—C12—Cl1119.6 (3)
C13—C14—C15118.0 (4)C21—C20—C19120.0 (4)
C9—C14—C15123.3 (4)C21—C20—H20120.0
O2—C15—C16120.8 (4)C19—C20—H20120.0
O2—C15—C14118.4 (4)C4—C5—C6118.3 (4)
C16—C15—C14120.7 (3)C4—C5—H5120.8
C17—C16—C21118.8 (4)C6—C5—H5120.8
C17—C16—C15121.5 (4)C5—C4—C3121.1 (4)
C21—C16—C15119.6 (4)C5—C4—H4119.5
C18—C17—C16120.2 (4)C3—C4—H4119.5
C18—C17—H17119.9C20—C21—C16120.7 (4)
C16—C17—H17119.9C20—C21—H21119.7
C12—C13—C14120.3 (4)C16—C21—H21119.7
C12—C13—H13119.8C3—C2—C1118.2 (4)
C14—C13—H13119.8C3—C2—H2120.9
O1—C9—C10123.6 (4)C1—C2—H2120.9
O1—C9—C14116.1 (3)C2—C3—C4121.4 (4)
C10—C9—C14120.4 (4)C2—C3—H3119.3
C18—C19—C20119.8 (4)C4—C3—H3119.3
C18—C19—H19120.1
C7—N1—C6—C5−178.9 (4)O1—C9—C10—C11−179.8 (4)
C7—N1—C6—C10.2 (5)C14—C9—C10—C11−1.0 (6)
C6—N1—C7—C8178.7 (4)C20—C19—C18—C17−0.5 (7)
C6—N1—C7—S1−0.7 (5)C16—C17—C18—C19−0.4 (6)
C1—S1—C7—N10.8 (3)C9—C10—C11—C121.0 (7)
C1—S1—C7—C8−178.6 (3)N1—C6—C1—C2−178.7 (4)
C9—O1—C8—C7−177.9 (3)C5—C6—C1—C20.5 (7)
N1—C7—C8—O1177.7 (4)N1—C6—C1—S10.4 (5)
S1—C7—C8—O1−2.9 (5)C5—C6—C1—S1179.6 (3)
C13—C14—C15—O2−42.2 (5)C7—S1—C1—C2178.3 (5)
C9—C14—C15—O2132.7 (4)C7—S1—C1—C6−0.6 (3)
C13—C14—C15—C16135.0 (4)C10—C11—C12—C130.5 (7)
C9—C14—C15—C16−50.1 (6)C10—C11—C12—Cl1−179.2 (3)
O2—C15—C16—C17152.4 (4)C14—C13—C12—C11−2.0 (6)
C14—C15—C16—C17−24.8 (6)C14—C13—C12—Cl1177.7 (3)
O2—C15—C16—C21−24.3 (6)C18—C19—C20—C211.6 (7)
C14—C15—C16—C21158.5 (4)N1—C6—C5—C4178.8 (4)
C21—C16—C17—C180.1 (6)C1—C6—C5—C4−0.3 (6)
C15—C16—C17—C18−176.6 (4)C6—C5—C4—C30.0 (7)
C9—C14—C13—C122.0 (6)C19—C20—C21—C16−1.9 (7)
C15—C14—C13—C12177.1 (4)C17—C16—C21—C201.1 (7)
C8—O1—C9—C106.1 (6)C15—C16—C21—C20177.8 (4)
C8—O1—C9—C14−172.8 (3)C6—C1—C2—C3−0.5 (7)
C13—C14—C9—O1178.4 (3)S1—C1—C2—C3−179.3 (4)
C15—C14—C9—O13.6 (6)C1—C2—C3—C40.2 (8)
C13—C14—C9—C10−0.5 (6)C5—C4—C3—C20.0 (8)
C15—C14—C9—C10−175.3 (4)
D—H···AD—HH···AD···AD—H···A
C17—H17···N1i0.952.563.432 (5)153
C5—H5···O2ii0.952.593.478 (5)155
C18—H18···Cg1iii0.952.623.433 (5)144
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the S1/C1/C6/N1/C7 ring.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C17—H17⋯N1i 0.952.563.432 (5)153
C5—H5⋯O2ii 0.952.593.478 (5)155
C18—H18⋯Cg1iii 0.952.623.433 (5)144

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

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Authors:  Vikas N Telvekar; Vinod Kumar Bairwa; Kalpana Satardekar; Anirudh Bellubi
Journal:  Bioorg Med Chem Lett       Date:  2011-10-30       Impact factor: 2.823

2.  A short history of SHELX.

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

3.  Synthesis, characterization and biological evaluation of some thiourea derivatives bearing benzothiazole moiety as potential antimicrobial and anticancer agents.

Authors:  Sohail Saeed; Naghmana Rashid; Peter G Jones; Muhammad Ali; Rizwan Hussain
Journal:  Eur J Med Chem       Date:  2009-12-16       Impact factor: 6.514

4.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
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  4 in total
  3 in total

1.  [2-(1,3-Benzothia-zol-2-ylmeth-oxy)-5-bromo-phen-yl](4-chloro-phen-yl)methanone.

Authors:  Susanta K Nayak; K N Venugopala; Thavendran Govender; Hendrik G Kruger; Glenn E M Maguire
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-12-12

2.  {2-[(1,3-Benzo-thia-zol-2-yl)meth-oxy]-5-chloro-phen-yl}(4-chloro-phen-yl)methan-one.

Authors:  K N Venugopala; Susanta K Nayak; B Odhav
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-06-19

3.  {2-[(1,3-Benzo-thia-zol-2-yl)meth-oxy]-5-fluoro-phen-yl}(4-chloro-phen-yl)methanone.

Authors:  K N Venugopala; Susanta K Nayak; Thavendran Govender; Hendrik G Kruger; Glenn E M Maguire
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-06-08
  3 in total

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