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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o67.
Published online 2007 December 6. doi:  10.1107/S160053680706165X
PMCID: PMC2915025

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

Abstract

Geometric parameters of the title compound, C24H20N2O2S, are in the usual ranges. The central heterocycle makes dihedral angles of 41.29 (4) and 72.94 (5)° with the phenyl ring and the methoxy­phenyl ring, respectively.

Related literature

For related literature, see: Arcadi et al. (2003 [triangle]); Bae et al. (2005 [triangle]); Bonde & Gaikwad (2004 [triangle]); Kim et al. (2007 [triangle]); Lee & Sim (2000 [triangle]); Manaka et al. (2005 [triangle]); Saeed & Parvez (2006 [triangle]); Sanemitsu et al. (2006 [triangle]); Shehata et al. (1996 [triangle]); Shih & Ke (2004 [triangle]); Venkatachalan et al. (2001 [triangle]).

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Object name is e-64-00o67-scheme1.jpg

Experimental

Crystal data

  • C24H20N2O2S
  • M r = 400.48
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-00o67-efi1.jpg
  • a = 10.1305 (10) Å
  • b = 20.0583 (14) Å
  • c = 10.0959 (10) Å
  • β = 102.710 (8)°
  • V = 2001.2 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.19 mm−1
  • T = 173 (2) K
  • 0.33 × 0.23 × 0.22 mm

Data collection

  • Stoe IPDSII two-circlediffractometer
  • Absorption correction: multi-scan (MULABS; Spek, 2003 [triangle]; Blessing, 1995 [triangle]) T min = 0.942, T max = 0.951
  • 11964 measured reflections
  • 3728 independent reflections
  • 3095 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.103
  • S = 1.05
  • 3728 reflections
  • 264 parameters
  • H-atom parameters constrained
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.28 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 [triangle]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680706165X/sg2195sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706165X/sg2195Isup2.hkl

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

Acknowledgments

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

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 act as a skin whitening agent (Kim et al., 2007). 4-Phenyl-2-hyrazono?thiazolines exhibit potent DPPH radical scavenging activity (Shih & Ke, 2004). 3-Alkyl-3H-thiazoline derivative PS-028 acts as potent and selective GPllb/llla antagonist (Manaka et al., 2005). 2-Acylimino-1,3-thiazolines show bleaching herbicidal activity (Sanemitsu et al., 2006) and 2-phenylimino-1,3-thiazolines show significant antifungal activity against rice blast fungus Pyricularia oryzae (Bae et al., 2005).

Geometric parameters of the title compound are in the usual ranges. The dihedral angles between the central heterocycle and the phenyl ring is 41.29 (4)and 72.94 (5)° for the methoxyphenyl ring.

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

All H atoms were located in a difference map. They were geometrically positioned and refined with fixed individual displacement parameters [U(H) = 1.2 Ueq(C) or U(H) = 1.5 Ueq(Cmethyl)] using a riding model with C—H ranging from 0.95Å to 0.98 Å.

Figures

Fig. 1.
Molecular structure of title compound with displacement ellipsoids at the 50% probability level.

Crystal data

C24H20N2O2SF000 = 840
Mr = 400.48Dx = 1.329 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 10726 reflections
a = 10.1305 (10) Åθ = 3.8–25.8º
b = 20.0583 (14) ŵ = 0.19 mm1
c = 10.0959 (10) ÅT = 173 (2) K
β = 102.710 (8)ºBlock, colourless
V = 2001.2 (3) Å30.33 × 0.23 × 0.22 mm
Z = 4

Data collection

Stoe IPDSII two-circle diffractometer3728 independent reflections
Radiation source: fine-focus sealed tube3095 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.039
T = 173(2) Kθmax = 25.6º
ω scansθmin = 3.7º
Absorption correction: multi-scan(MULABS; Spek, 2003; Blessing, 1995)h = −12→11
Tmin = 0.942, Tmax = 0.951k = −21→24
11964 measured reflectionsl = −12→12

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.103  w = 1/[σ2(Fo2) + (0.0627P)2 + 0.2151P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
3728 reflectionsΔρmax = 0.15 e Å3
264 parametersΔρmin = −0.28 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
S10.98050 (4)0.70737 (2)0.51355 (5)0.04086 (15)
O11.10348 (11)0.68440 (6)0.31286 (12)0.0397 (3)
O20.72991 (11)0.52503 (5)0.53280 (10)0.0332 (3)
N10.75221 (12)0.64830 (6)0.43148 (12)0.0265 (3)
N20.89232 (13)0.63407 (6)0.27787 (12)0.0295 (3)
C10.87220 (15)0.65906 (7)0.39275 (15)0.0281 (3)
C20.74474 (16)0.67752 (8)0.55719 (15)0.0305 (3)
C30.86066 (19)0.70950 (9)0.61315 (18)0.0434 (4)
H30.87550.73110.69890.052*
C41.01248 (15)0.64968 (7)0.24281 (15)0.0303 (3)
C111.02529 (15)0.62264 (8)0.10802 (15)0.0301 (3)
C120.91665 (16)0.59116 (8)0.02041 (16)0.0347 (4)
H120.83350.58510.04780.042*
C130.92970 (18)0.56869 (9)−0.10637 (17)0.0396 (4)
H130.85480.5478−0.16490.047*
C141.05099 (17)0.57628 (9)−0.14929 (16)0.0354 (4)
C151.15848 (17)0.60780 (10)−0.06097 (17)0.0397 (4)
H151.24180.6135−0.08810.048*
C161.14651 (16)0.63095 (9)0.06546 (17)0.0372 (4)
H161.22100.65250.12320.045*
C171.0679 (2)0.54980 (10)−0.28494 (17)0.0462 (4)
H17A1.08970.5022−0.27670.069*
H17B1.14150.5738−0.31300.069*
H17C0.98360.5563−0.35300.069*
C210.65588 (14)0.60120 (7)0.35548 (14)0.0254 (3)
C220.64954 (14)0.53698 (7)0.40723 (14)0.0259 (3)
C230.56515 (16)0.48964 (8)0.32885 (15)0.0329 (4)
H230.55860.44590.36290.040*
C240.49103 (17)0.50720 (9)0.20088 (16)0.0379 (4)
H240.43450.47490.14730.045*
C250.49813 (17)0.57099 (9)0.14992 (16)0.0387 (4)
H250.44640.58220.06240.046*
C260.58140 (16)0.61869 (8)0.22749 (14)0.0326 (4)
H260.58710.66250.19330.039*
C270.74026 (19)0.45719 (8)0.58037 (16)0.0369 (4)
H27A0.65060.44110.58720.055*
H27B0.80190.45510.66990.055*
H27C0.77530.42910.51640.055*
C310.62025 (16)0.67828 (7)0.61048 (15)0.0297 (3)
C320.63140 (18)0.67578 (8)0.75194 (15)0.0358 (4)
H320.71700.66770.81070.043*
C330.5178 (2)0.68500 (8)0.80611 (17)0.0415 (4)
H330.52640.68270.90160.050*
C340.3918 (2)0.69747 (9)0.72213 (18)0.0414 (4)
H340.31510.70500.76000.050*
C350.37924 (18)0.69885 (8)0.58204 (17)0.0367 (4)
H350.29330.70680.52380.044*
C360.49179 (16)0.68870 (7)0.52706 (15)0.0313 (3)
H360.48150.68880.43120.038*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0358 (2)0.0385 (3)0.0506 (3)−0.01358 (18)0.01446 (18)−0.01702 (18)
O10.0342 (6)0.0394 (7)0.0465 (7)−0.0054 (5)0.0112 (5)−0.0059 (5)
O20.0418 (6)0.0246 (5)0.0292 (5)−0.0013 (5)−0.0009 (5)0.0015 (4)
N10.0299 (6)0.0224 (6)0.0278 (6)−0.0030 (5)0.0074 (5)−0.0025 (5)
N20.0315 (7)0.0266 (6)0.0318 (6)0.0011 (5)0.0098 (5)0.0012 (5)
C10.0300 (8)0.0209 (7)0.0335 (7)0.0003 (6)0.0075 (6)0.0014 (6)
C20.0381 (8)0.0246 (7)0.0301 (7)−0.0034 (7)0.0102 (6)−0.0061 (6)
C30.0458 (10)0.0424 (10)0.0444 (9)−0.0146 (8)0.0153 (8)−0.0194 (8)
C40.0290 (8)0.0249 (8)0.0377 (8)0.0040 (6)0.0089 (6)0.0051 (6)
C110.0295 (8)0.0274 (8)0.0347 (8)0.0062 (6)0.0098 (6)0.0071 (6)
C120.0290 (8)0.0376 (9)0.0402 (9)0.0020 (7)0.0131 (6)−0.0002 (7)
C130.0342 (9)0.0455 (10)0.0393 (9)0.0014 (7)0.0088 (7)−0.0037 (7)
C140.0354 (8)0.0383 (9)0.0344 (8)0.0095 (7)0.0120 (7)0.0077 (7)
C150.0326 (8)0.0507 (11)0.0392 (9)0.0038 (8)0.0155 (7)0.0099 (7)
C160.0298 (8)0.0444 (10)0.0382 (8)0.0011 (7)0.0090 (7)0.0071 (7)
C170.0479 (10)0.0561 (12)0.0390 (9)0.0069 (9)0.0192 (8)0.0026 (8)
C210.0251 (7)0.0268 (7)0.0249 (7)−0.0006 (6)0.0065 (5)−0.0047 (5)
C220.0259 (7)0.0269 (8)0.0252 (7)0.0000 (6)0.0062 (6)−0.0033 (5)
C230.0337 (8)0.0296 (8)0.0367 (8)−0.0051 (7)0.0103 (7)−0.0074 (6)
C240.0332 (9)0.0449 (10)0.0342 (8)−0.0064 (7)0.0049 (7)−0.0146 (7)
C250.0347 (9)0.0527 (11)0.0261 (7)0.0031 (8)0.0007 (6)−0.0055 (7)
C260.0350 (8)0.0357 (9)0.0269 (7)0.0044 (7)0.0065 (6)0.0011 (6)
C270.0517 (10)0.0259 (8)0.0336 (8)0.0036 (7)0.0102 (7)0.0035 (6)
C310.0389 (8)0.0202 (7)0.0319 (7)−0.0040 (6)0.0118 (6)−0.0053 (6)
C320.0468 (10)0.0290 (8)0.0317 (8)−0.0007 (7)0.0091 (7)−0.0047 (6)
C330.0645 (12)0.0316 (9)0.0333 (8)−0.0023 (8)0.0212 (8)−0.0042 (7)
C340.0509 (10)0.0318 (9)0.0492 (10)−0.0048 (8)0.0277 (8)−0.0057 (7)
C350.0385 (9)0.0293 (8)0.0443 (9)−0.0025 (7)0.0134 (7)−0.0043 (7)
C360.0410 (9)0.0233 (7)0.0311 (8)−0.0030 (7)0.0110 (6)−0.0025 (6)

Geometric parameters (Å, °)

S1—C31.7390 (19)C17—H17B0.9800
S1—C11.7439 (15)C17—H17C0.9800
O1—C41.2442 (19)C21—C261.3903 (19)
O2—C221.3687 (17)C21—C221.397 (2)
O2—C271.4392 (18)C22—C231.400 (2)
N1—C11.373 (2)C23—C241.389 (2)
N1—C21.4151 (19)C23—H230.9500
N1—C211.4505 (17)C24—C251.387 (3)
N2—C11.320 (2)C24—H240.9500
N2—C41.376 (2)C25—C261.396 (2)
C2—C31.348 (2)C25—H250.9500
C2—C311.476 (2)C26—H260.9500
C3—H30.9500C27—H27A0.9800
C4—C111.497 (2)C27—H27B0.9800
C11—C161.397 (2)C27—H27C0.9800
C11—C121.401 (2)C31—C361.402 (2)
C12—C131.390 (2)C31—C321.409 (2)
C12—H120.9500C32—C331.390 (2)
C13—C141.398 (2)C32—H320.9500
C13—H130.9500C33—C341.391 (3)
C14—C151.398 (2)C33—H330.9500
C14—C171.514 (2)C34—C351.392 (2)
C15—C161.388 (2)C34—H340.9500
C15—H150.9500C35—C361.388 (2)
C16—H160.9500C35—H350.9500
C17—H17A0.9800C36—H360.9500
C3—S1—C190.36 (8)C26—C21—C22121.34 (13)
C22—O2—C27117.35 (11)C26—C21—N1119.45 (14)
C1—N1—C2114.55 (12)C22—C21—N1118.93 (12)
C1—N1—C21119.11 (12)O2—C22—C21116.16 (12)
C2—N1—C21125.57 (13)O2—C22—C23124.72 (14)
C1—N2—C4117.12 (13)C21—C22—C23119.12 (13)
N2—C1—N1120.52 (13)C24—C23—C22119.43 (15)
N2—C1—S1129.09 (12)C24—C23—H23120.3
N1—C1—S1110.39 (10)C22—C23—H23120.3
C3—C2—N1111.07 (14)C25—C24—C23121.16 (14)
C3—C2—C31125.28 (14)C25—C24—H24119.4
N1—C2—C31123.35 (13)C23—C24—H24119.4
C2—C3—S1113.61 (12)C24—C25—C26119.89 (14)
C2—C3—H3123.2C24—C25—H25120.1
S1—C3—H3123.2C26—C25—H25120.1
O1—C4—N2124.59 (15)C21—C26—C25119.06 (15)
O1—C4—C11121.19 (15)C21—C26—H26120.5
N2—C4—C11114.19 (13)C25—C26—H26120.5
C16—C11—C12118.75 (15)O2—C27—H27A109.5
C16—C11—C4119.62 (14)O2—C27—H27B109.5
C12—C11—C4121.59 (14)H27A—C27—H27B109.5
C13—C12—C11120.43 (16)O2—C27—H27C109.5
C13—C12—H12119.8H27A—C27—H27C109.5
C11—C12—H12119.8H27B—C27—H27C109.5
C12—C13—C14121.20 (16)C36—C31—C32118.12 (15)
C12—C13—H13119.4C36—C31—C2122.50 (13)
C14—C13—H13119.4C32—C31—C2119.00 (14)
C15—C14—C13117.78 (15)C33—C32—C31120.35 (15)
C15—C14—C17120.57 (16)C33—C32—H32119.8
C13—C14—C17121.64 (16)C31—C32—H32119.8
C16—C15—C14121.64 (16)C32—C33—C34120.80 (15)
C16—C15—H15119.2C32—C33—H33119.6
C14—C15—H15119.2C34—C33—H33119.6
C15—C16—C11120.21 (15)C33—C34—C35119.30 (17)
C15—C16—H16119.9C33—C34—H34120.4
C11—C16—H16119.9C35—C34—H34120.4
C14—C17—H17A109.5C36—C35—C34120.24 (16)
C14—C17—H17B109.5C36—C35—H35119.9
H17A—C17—H17B109.5C34—C35—H35119.9
C14—C17—H17C109.5C35—C36—C31121.14 (14)
H17A—C17—H17C109.5C35—C36—H36119.4
H17B—C17—H17C109.5C31—C36—H36119.4
C4—N2—C1—N1176.95 (12)C4—C11—C16—C15−178.16 (15)
C4—N2—C1—S1−3.0 (2)C1—N1—C21—C26−73.97 (18)
C2—N1—C1—N2179.56 (13)C2—N1—C21—C26116.67 (16)
C21—N1—C1—N29.1 (2)C1—N1—C21—C2299.99 (16)
C2—N1—C1—S1−0.48 (15)C2—N1—C21—C22−69.38 (19)
C21—N1—C1—S1−170.98 (10)C27—O2—C22—C21−171.39 (14)
C3—S1—C1—N2−178.83 (15)C27—O2—C22—C237.6 (2)
C3—S1—C1—N11.21 (12)C26—C21—C22—O2178.36 (13)
C1—N1—C2—C3−0.81 (19)N1—C21—C22—O24.5 (2)
C21—N1—C2—C3168.98 (15)C26—C21—C22—C23−0.7 (2)
C1—N1—C2—C31173.17 (13)N1—C21—C22—C23−174.56 (13)
C21—N1—C2—C31−17.0 (2)O2—C22—C23—C24−178.17 (15)
N1—C2—C3—S11.76 (19)C21—C22—C23—C240.8 (2)
C31—C2—C3—S1−172.09 (12)C22—C23—C24—C25−0.6 (2)
C1—S1—C3—C2−1.74 (15)C23—C24—C25—C260.3 (3)
C1—N2—C4—O11.4 (2)C22—C21—C26—C250.4 (2)
C1—N2—C4—C11−176.94 (12)N1—C21—C26—C25174.20 (14)
O1—C4—C11—C166.2 (2)C24—C25—C26—C21−0.2 (2)
N2—C4—C11—C16−175.35 (13)C3—C2—C31—C36134.02 (18)
O1—C4—C11—C12−171.36 (15)N1—C2—C31—C36−39.1 (2)
N2—C4—C11—C127.1 (2)C3—C2—C31—C32−38.8 (2)
C16—C11—C12—C130.0 (2)N1—C2—C31—C32148.05 (15)
C4—C11—C12—C13177.59 (15)C36—C31—C32—C33−1.4 (2)
C11—C12—C13—C140.6 (3)C2—C31—C32—C33171.72 (14)
C12—C13—C14—C15−0.6 (3)C31—C32—C33—C34−0.6 (3)
C12—C13—C14—C17177.76 (16)C32—C33—C34—C351.8 (3)
C13—C14—C15—C160.1 (3)C33—C34—C35—C36−0.8 (2)
C17—C14—C15—C16−178.30 (16)C34—C35—C36—C31−1.3 (2)
C14—C15—C16—C110.5 (3)C32—C31—C36—C352.4 (2)
C12—C11—C16—C15−0.5 (2)C2—C31—C36—C35−170.49 (14)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SG2195).

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