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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o66.
Published online 2007 December 6. doi:  10.1107/S1600536807062290
PMCID: PMC2915024

(Z)-N-[3-(2-Methoxy­phen­yl)-4-phenyl-2,3-dihydro­thia­zol-2-yl­idene]-2-methyl­benzamide

Abstract

In the title mol­ecule, C24H20N2O2S, the thia­zole and amide groups are essentially coplanar. The thia­zole ring forms dihedral angles of 61.62 (4) and 26.75 (5)° with the benzene rings of the methoxy­phenyl and methyl­phenyl groups, respectively, and 33.69 (6)° with the phenyl ring. The crystal packing is stabilized by inter­molecular C—H(...)O hydrogen bonds, forming a three-dimensional network.

Related literature

For related literature, see: Arcadi et al. (2003 [triangle]); Bonde & Gaikwad (2004 [triangle]); Kim et al. (2007 [triangle]); Lee & Sim (2000 [triangle]); Saeed & Parvez (2006 [triangle]); Shehata et al. (1996 [triangle]); Venkatachalan et al. (2001 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-00o66-scheme1.jpg

Experimental

Crystal data

  • C24H20N2O2S
  • M r = 400.48
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-00o66-efi1.jpg
  • a = 9.7826 (18) Å
  • b = 15.010 (3) Å
  • c = 13.917 (3) Å
  • β = 105.092 (4)°
  • V = 1973.1 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.19 mm−1
  • T = 153 (2) K
  • 0.50 × 0.40 × 0.25 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2002 [triangle]) T min = 0.912, T max = 0.955
  • 16940 measured reflections
  • 4697 independent reflections
  • 4150 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.102
  • S = 1.04
  • 4697 reflections
  • 264 parameters
  • H-atom parameters constrained
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2002 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807062290/lh2546sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062290/lh2546Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

AS gratefully acknowledges a research grant from Quaid-i-Azam University, Islamabad.

supplementary crystallographic information

Comment

2-Imino derivatives of 1,3-thiazolines posses a wide range of pharmacological and synthetic applications. Thus, these show potent bioactivities ranging from antitubercular (Shehata et al., 1996) to anti-HIV (Venkatachalan et al., 2001) activities. Iminothiazolines containing a pyrazine ring show significant antibacterial and antimicrobial activity (Bonde & Gaikwad 2004), derivatives of rhodanine show antibacterial, anti-inflammatory and antiviral activities (Lee & Sim et al., 2000) and bis-thiazoline derivatives show marked anti-cancer activity against human cell lines (Arcadi et al., 2003). A 2-imino-1,3-thiazoline derivative KHG22394 acts as a skin whitening agent (Kim et al., 2007).

Experimental

The title compound was prepared according to the method reported earlier (Saeed & Parvez 2006). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution. Full spectroscopic and physical characterization will be reported elsewhere.

Refinement

Hydrogen atoms were located in difference syntheses, refined at idealized positions riding on the C (C–H = 0.95–0.98 Å) atoms with isotropic displacement parameters Uiso(H) = 1.2U(Ceq) and 1.5(methyl-C). Methyl H atoms were refined on the basis of rigid groups allowed to rotate but not tip.

Figures

Fig. 1.
Molecular structure of title compound. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Crystal packing viewed along [010] with intermolecular hydrogen bonding pattern indicated as dashed lines. H-atoms not involved in hydrogen bonding are omitted.

Crystal data

C24H20N2O2SF000 = 840
Mr = 400.48Dx = 1.348 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 989 reflections
a = 9.7826 (18) Åθ = 2.6–28.3º
b = 15.010 (3) ŵ = 0.19 mm1
c = 13.917 (3) ÅT = 153 (2) K
β = 105.092 (4)ºPrism, colourless
V = 1973.1 (6) Å30.50 × 0.40 × 0.25 mm
Z = 4

Data collection

Bruker AXS SMART APEX diffractometer4697 independent reflections
Radiation source: sealed tube4150 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.025
T = 153(2) Kθmax = 27.9º
[var phi] and ω scansθmin = 2.0º
Absorption correction: multi-scan(SADABS; Bruker, 2002)h = −11→12
Tmin = 0.912, Tmax = 0.955k = −19→19
16940 measured reflectionsl = −18→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.102  w = 1/[σ2(Fo2) + (0.0517P)2 + 0.8403P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
4697 reflectionsΔρmax = 0.34 e Å3
264 parametersΔρmin = −0.21 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S10.63733 (3)0.65129 (2)0.82089 (3)0.02247 (10)
O10.72271 (10)0.57226 (7)0.68165 (8)0.0258 (2)
O20.16287 (9)0.62604 (6)0.76469 (7)0.0212 (2)
N10.52745 (11)0.50297 (7)0.71108 (8)0.0196 (2)
N20.42303 (11)0.55761 (7)0.83194 (8)0.0177 (2)
C10.63503 (13)0.51125 (9)0.66513 (10)0.0202 (3)
C20.64098 (13)0.43708 (9)0.59434 (10)0.0214 (3)
C30.58372 (15)0.35480 (9)0.61069 (11)0.0260 (3)
H3A0.54180.34860.66470.031*
C40.58680 (16)0.28229 (10)0.55010 (11)0.0301 (3)
H4A0.54880.22660.56280.036*
C50.64615 (16)0.29210 (10)0.47064 (11)0.0316 (3)
H5A0.64770.24310.42780.038*
C60.70292 (16)0.37264 (11)0.45352 (11)0.0303 (3)
H6A0.74340.37790.39870.036*
C70.70292 (14)0.44716 (10)0.51435 (10)0.0243 (3)
C80.76269 (16)0.53331 (11)0.48825 (11)0.0313 (3)
H8A0.85770.54230.53220.047*
H8B0.70130.58270.49660.047*
H8C0.76800.53110.41890.047*
C90.52416 (13)0.56139 (8)0.77971 (9)0.0184 (2)
C100.54693 (14)0.67709 (9)0.90914 (10)0.0237 (3)
H10A0.57290.72480.95510.028*
C110.43667 (13)0.62292 (8)0.90605 (9)0.0197 (2)
C120.34425 (13)0.62715 (9)0.97466 (9)0.0206 (3)
C130.31678 (15)0.71102 (10)1.00913 (11)0.0265 (3)
H13A0.35130.76300.98430.032*
C140.23944 (16)0.71898 (11)1.07930 (11)0.0317 (3)
H14A0.22320.77611.10360.038*
C150.18594 (17)0.64354 (11)1.11381 (12)0.0331 (3)
H15A0.13260.64891.16160.040*
C160.21014 (16)0.56054 (11)1.07879 (11)0.0306 (3)
H16A0.17160.50911.10160.037*
C170.29047 (15)0.55166 (9)1.01040 (10)0.0247 (3)
H17A0.30870.49420.98800.030*
C180.30424 (13)0.49851 (8)0.79994 (9)0.0180 (2)
C190.32421 (14)0.40723 (9)0.80007 (10)0.0218 (3)
H19A0.41620.38280.82510.026*
C200.20894 (16)0.35139 (9)0.76347 (11)0.0252 (3)
H20A0.22190.28870.76180.030*
C210.07491 (15)0.38805 (9)0.72938 (10)0.0254 (3)
H21A−0.00380.34980.70470.031*
C220.05328 (14)0.47927 (9)0.73060 (10)0.0223 (3)
H22A−0.03950.50320.70860.027*
C230.16958 (13)0.53563 (8)0.76461 (9)0.0182 (2)
C240.02588 (16)0.66550 (10)0.73440 (16)0.0415 (4)
H24A−0.01760.65100.66450.062*
H24B0.03440.73030.74220.062*
H24C−0.03340.64230.77570.062*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.01853 (16)0.02102 (16)0.02916 (18)−0.00347 (11)0.00855 (13)−0.00330 (12)
O10.0212 (5)0.0285 (5)0.0302 (5)−0.0048 (4)0.0112 (4)−0.0021 (4)
O20.0164 (4)0.0192 (4)0.0274 (5)0.0005 (3)0.0045 (4)0.0000 (4)
N10.0162 (5)0.0221 (5)0.0212 (5)−0.0002 (4)0.0064 (4)−0.0009 (4)
N20.0153 (5)0.0183 (5)0.0199 (5)−0.0009 (4)0.0053 (4)−0.0015 (4)
C10.0174 (6)0.0235 (6)0.0197 (6)0.0018 (5)0.0049 (5)0.0030 (5)
C20.0167 (6)0.0278 (6)0.0192 (6)0.0047 (5)0.0041 (5)0.0001 (5)
C30.0260 (7)0.0278 (7)0.0252 (7)0.0022 (5)0.0085 (5)−0.0014 (5)
C40.0310 (7)0.0269 (7)0.0307 (7)0.0045 (6)0.0051 (6)−0.0015 (6)
C50.0324 (8)0.0340 (8)0.0263 (7)0.0113 (6)0.0039 (6)−0.0068 (6)
C60.0277 (7)0.0432 (8)0.0209 (7)0.0085 (6)0.0081 (6)−0.0014 (6)
C70.0180 (6)0.0352 (7)0.0191 (6)0.0048 (5)0.0040 (5)0.0018 (5)
C80.0310 (8)0.0423 (8)0.0227 (7)−0.0043 (6)0.0108 (6)0.0020 (6)
C90.0149 (5)0.0196 (6)0.0203 (6)0.0003 (4)0.0036 (5)0.0016 (5)
C100.0215 (6)0.0227 (6)0.0273 (7)−0.0009 (5)0.0071 (5)−0.0060 (5)
C110.0188 (6)0.0201 (6)0.0192 (6)0.0023 (5)0.0034 (5)−0.0016 (5)
C120.0173 (6)0.0261 (6)0.0171 (6)0.0025 (5)0.0023 (5)−0.0024 (5)
C130.0239 (7)0.0267 (7)0.0294 (7)0.0000 (5)0.0079 (6)−0.0057 (5)
C140.0297 (7)0.0349 (8)0.0318 (8)0.0049 (6)0.0105 (6)−0.0110 (6)
C150.0308 (8)0.0453 (9)0.0266 (7)0.0087 (7)0.0138 (6)−0.0007 (6)
C160.0323 (8)0.0359 (8)0.0260 (7)0.0055 (6)0.0118 (6)0.0072 (6)
C170.0261 (7)0.0265 (7)0.0218 (6)0.0053 (5)0.0067 (5)0.0012 (5)
C180.0174 (6)0.0209 (6)0.0169 (6)−0.0031 (5)0.0069 (5)−0.0012 (4)
C190.0234 (6)0.0220 (6)0.0221 (6)0.0009 (5)0.0101 (5)0.0011 (5)
C200.0327 (7)0.0184 (6)0.0289 (7)−0.0034 (5)0.0159 (6)−0.0015 (5)
C210.0259 (7)0.0266 (7)0.0271 (7)−0.0098 (5)0.0129 (6)−0.0064 (5)
C220.0181 (6)0.0267 (6)0.0236 (6)−0.0034 (5)0.0080 (5)−0.0027 (5)
C230.0195 (6)0.0199 (6)0.0169 (6)−0.0017 (5)0.0077 (5)−0.0005 (4)
C240.0209 (7)0.0249 (7)0.0752 (13)0.0040 (6)0.0063 (8)−0.0046 (8)

Geometric parameters (Å, °)

S1—C101.7337 (14)C10—H10A0.9500
S1—C91.7449 (13)C11—C121.4774 (17)
O1—C11.2347 (16)C12—C171.3943 (19)
O2—C231.3587 (15)C12—C131.3980 (18)
O2—C241.4248 (17)C13—C141.3875 (19)
N1—C91.3032 (17)C13—H13A0.9500
N1—C11.3720 (16)C14—C151.385 (2)
N2—C91.3730 (16)C14—H14A0.9500
N2—C111.4039 (16)C15—C161.381 (2)
N2—C181.4373 (16)C15—H15A0.9500
C1—C21.4978 (18)C16—C171.3896 (19)
C2—C31.3991 (19)C16—H16A0.9500
C2—C71.4073 (18)C17—H17A0.9500
C3—C41.382 (2)C18—C191.3840 (18)
C3—H3A0.9500C18—C231.3965 (18)
C4—C51.384 (2)C19—C201.3909 (19)
C4—H4A0.9500C19—H19A0.9500
C5—C61.377 (2)C20—C211.387 (2)
C5—H5A0.9500C20—H20A0.9500
C6—C71.403 (2)C21—C221.386 (2)
C6—H6A0.9500C21—H21A0.9500
C7—C81.502 (2)C22—C231.3978 (18)
C8—H8A0.9800C22—H22A0.9500
C8—H8B0.9800C24—H24A0.9800
C8—H8C0.9800C24—H24B0.9800
C10—C111.3425 (18)C24—H24C0.9800
C10—S1—C990.48 (6)C17—C12—C13119.04 (12)
C23—O2—C24117.19 (11)C17—C12—C11123.15 (12)
C9—N1—C1116.67 (11)C13—C12—C11117.71 (12)
C9—N2—C11114.60 (10)C14—C13—C12120.51 (14)
C9—N2—C18119.83 (10)C14—C13—H13A119.7
C11—N2—C18124.97 (10)C12—C13—H13A119.7
O1—C1—N1124.08 (12)C15—C14—C13119.89 (14)
O1—C1—C2121.99 (11)C15—C14—H14A120.1
N1—C1—C2113.90 (11)C13—C14—H14A120.1
C3—C2—C7119.77 (13)C16—C15—C14120.03 (13)
C3—C2—C1117.61 (12)C16—C15—H15A120.0
C7—C2—C1122.61 (12)C14—C15—H15A120.0
C4—C3—C2121.52 (13)C15—C16—C17120.52 (14)
C4—C3—H3A119.2C15—C16—H16A119.7
C2—C3—H3A119.2C17—C16—H16A119.7
C3—C4—C5118.94 (14)C16—C17—C12119.97 (13)
C3—C4—H4A120.5C16—C17—H17A120.0
C5—C4—H4A120.5C12—C17—H17A120.0
C6—C5—C4120.24 (13)C19—C18—C23121.02 (12)
C6—C5—H5A119.9C19—C18—N2120.54 (11)
C4—C5—H5A119.9C23—C18—N2118.38 (11)
C5—C6—C7122.17 (13)C18—C19—C20119.70 (13)
C5—C6—H6A118.9C18—C19—H19A120.2
C7—C6—H6A118.9C20—C19—H19A120.2
C6—C7—C2117.34 (13)C21—C20—C19119.36 (12)
C6—C7—C8118.64 (13)C21—C20—H20A120.3
C2—C7—C8123.96 (13)C19—C20—H20A120.3
C7—C8—H8A109.5C22—C21—C20121.43 (12)
C7—C8—H8B109.5C22—C21—H21A119.3
H8A—C8—H8B109.5C20—C21—H21A119.3
C7—C8—H8C109.5C21—C22—C23119.25 (13)
H8A—C8—H8C109.5C21—C22—H22A120.4
H8B—C8—H8C109.5C23—C22—H22A120.4
N1—C9—N2121.26 (11)O2—C23—C18116.08 (11)
N1—C9—S1128.79 (10)O2—C23—C22124.72 (12)
N2—C9—S1109.95 (9)C18—C23—C22119.19 (12)
C11—C10—S1113.32 (10)O2—C24—H24A109.5
C11—C10—H10A123.3O2—C24—H24B109.5
S1—C10—H10A123.3H24A—C24—H24B109.5
C10—C11—N2111.61 (11)O2—C24—H24C109.5
C10—C11—C12125.11 (12)H24A—C24—H24C109.5
N2—C11—C12123.21 (11)H24B—C24—H24C109.5
C9—N1—C1—O1−3.59 (19)C18—N2—C11—C1212.82 (19)
C9—N1—C1—C2174.37 (11)C10—C11—C12—C17−142.16 (15)
O1—C1—C2—C3152.58 (13)N2—C11—C12—C1734.49 (19)
N1—C1—C2—C3−25.43 (17)C10—C11—C12—C1334.2 (2)
O1—C1—C2—C7−26.54 (19)N2—C11—C12—C13−149.19 (13)
N1—C1—C2—C7155.46 (12)C17—C12—C13—C141.2 (2)
C7—C2—C3—C40.3 (2)C11—C12—C13—C14−175.25 (13)
C1—C2—C3—C4−178.89 (13)C12—C13—C14—C15−1.6 (2)
C2—C3—C4—C5−1.0 (2)C13—C14—C15—C160.3 (2)
C3—C4—C5—C60.9 (2)C14—C15—C16—C171.3 (2)
C4—C5—C6—C7−0.2 (2)C15—C16—C17—C12−1.7 (2)
C5—C6—C7—C2−0.5 (2)C13—C12—C17—C160.4 (2)
C5—C6—C7—C8−177.96 (14)C11—C12—C17—C16176.67 (13)
C3—C2—C7—C60.48 (19)C9—N2—C18—C1963.62 (16)
C1—C2—C7—C6179.58 (12)C11—N2—C18—C19−125.79 (13)
C3—C2—C7—C8177.79 (13)C9—N2—C18—C23−113.51 (13)
C1—C2—C7—C8−3.1 (2)C11—N2—C18—C2357.08 (17)
C1—N1—C9—N2−178.30 (11)C23—C18—C19—C200.75 (19)
C1—N1—C9—S11.15 (18)N2—C18—C19—C20−176.30 (11)
C11—N2—C9—N1177.57 (11)C18—C19—C20—C21−1.45 (19)
C18—N2—C9—N1−10.90 (18)C19—C20—C21—C220.3 (2)
C11—N2—C9—S1−1.97 (13)C20—C21—C22—C231.6 (2)
C18—N2—C9—S1169.55 (9)C24—O2—C23—C18−176.49 (13)
C10—S1—C9—N1−177.59 (13)C24—O2—C23—C224.66 (19)
C10—S1—C9—N21.91 (10)C19—C18—C23—O2−177.78 (11)
C9—S1—C10—C11−1.49 (11)N2—C18—C23—O2−0.66 (16)
S1—C10—C11—N20.64 (15)C19—C18—C23—C221.13 (18)
S1—C10—C11—C12177.62 (10)N2—C18—C23—C22178.25 (11)
C9—N2—C11—C100.89 (16)C21—C22—C23—O2176.52 (12)
C18—N2—C11—C10−170.13 (12)C21—C22—C23—C18−2.29 (19)
C9—N2—C11—C12−176.15 (11)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3A···N10.952.422.7572 (18)101
C14—H14A···O1i0.952.523.4635 (19)171
C22—H22A···O1ii0.952.483.4240 (18)170

Symmetry codes: (i) x−1/2, −y+3/2, z+1/2; (ii) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2546).

References

  • Arcadi, A., Attanasi, O. A., Giorgi, G., Filippone, P., Rossi, E. & Santeusanio, S. (2003). Tetrahedron Lett.44, 8391–8394.
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