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

Saeed, A.; Zaman, S.; Flörke, U.

doi:10.1107/S1600536807062290

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o66

https://doi.org/10.1107/S1600536807062290

Open

access

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

Aamer Saeed,^a ^* Sabah Zaman ^a and Ulrich Flörke ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan, and ^bDepartment Chemie, Fakultät für Naturwissenschaften, Universität Paderborn, Warburgerstrasse 100, D-33098 Paderborn, Germany
^*Correspondence e-mail: aamersaeed@yahoo.com

(Received 30 October 2007; accepted 22 November 2007; online 6 December 2007)

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 ); Bonde & Gaikwad (2004 ); Kim et al. (2007 ); Lee & Sim (2000 ); Saeed & Parvez (2006 ); Shehata et al. (1996 ); Venkatachalan et al. (2001 ).

Experimental

Crystal data

C₂₄H₂₀N₂O₂S
M_r = 400.48
Monoclinic, P 2₁ /n
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 ) 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[F² > 2σ(F²)] = 0.038
wR(F²) = 0.102
S = 1.04
4697 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯N1	0.95	2.42	2.7572 (18)	101
C14—H14A⋯O1ⁱ	0.95	2.52	3.4635 (19)	171
C22—H22A⋯O1ⁱⁱ	0.95	2.48	3.4240 (18)	170
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x-1, y, z.

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

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807062290/lh2546Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Structure description top

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

Computing details top

Figures top

	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.

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

Crystal data top

C₂₄H₂₀N₂O₂S	F(000) = 840
M_r = 400.48	D_x = 1.348 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 989 reflections
a = 9.7826 (18) Å	θ = 2.6–28.3°
b = 15.010 (3) Å	µ = 0.19 mm⁻¹
c = 13.917 (3) Å	T = 153 K
β = 105.092 (4)°	Prism, colourless
V = 1973.1 (6) Å³	0.50 × 0.40 × 0.25 mm
Z = 4

Data collection top

Bruker AXS SMART APEX diffractometer	4697 independent reflections
Radiation source: sealed tube	4150 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
φ and ω scans	θ_max = 27.9°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −11→12
T_min = 0.912, T_max = 0.955	k = −19→19
16940 measured reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: difference Fourier map
wR(F²) = 0.102	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0517P)² + 0.8403P] where P = (F_o² + 2F_c²)/3
4697 reflections	(Δ/σ)_max = 0.001
264 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₄H₂₀N₂O₂S	V = 1973.1 (6) Å³
M_r = 400.48	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.7826 (18) Å	µ = 0.19 mm⁻¹
b = 15.010 (3) Å	T = 153 K
c = 13.917 (3) Å	0.50 × 0.40 × 0.25 mm
β = 105.092 (4)°

Data collection top

Bruker AXS SMART APEX diffractometer	4697 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	4150 reflections with I > 2σ(I)
T_min = 0.912, T_max = 0.955	R_int = 0.025
16940 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.04	Δρ_max = 0.34 e Å⁻³
4697 reflections	Δρ_min = −0.21 e Å⁻³
264 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
S1	0.63733 (3)	0.65129 (2)	0.82089 (3)	0.02247 (10)
O1	0.72271 (10)	0.57226 (7)	0.68165 (8)	0.0258 (2)
O2	0.16287 (9)	0.62604 (6)	0.76469 (7)	0.0212 (2)
N1	0.52745 (11)	0.50297 (7)	0.71108 (8)	0.0196 (2)
N2	0.42303 (11)	0.55761 (7)	0.83194 (8)	0.0177 (2)
C1	0.63503 (13)	0.51125 (9)	0.66513 (10)	0.0202 (3)
C2	0.64098 (13)	0.43708 (9)	0.59434 (10)	0.0214 (3)
C3	0.58372 (15)	0.35480 (9)	0.61069 (11)	0.0260 (3)
H3A	0.5418	0.3486	0.6647	0.031*
C4	0.58680 (16)	0.28229 (10)	0.55010 (11)	0.0301 (3)
H4A	0.5488	0.2266	0.5628	0.036*
C5	0.64615 (16)	0.29210 (10)	0.47064 (11)	0.0316 (3)
H5A	0.6477	0.2431	0.4278	0.038*
C6	0.70292 (16)	0.37264 (11)	0.45352 (11)	0.0303 (3)
H6A	0.7434	0.3779	0.3987	0.036*
C7	0.70292 (14)	0.44716 (10)	0.51435 (10)	0.0243 (3)
C8	0.76269 (16)	0.53331 (11)	0.48825 (11)	0.0313 (3)
H8A	0.8577	0.5423	0.5322	0.047*
H8B	0.7013	0.5827	0.4966	0.047*
H8C	0.7680	0.5311	0.4189	0.047*
C9	0.52416 (13)	0.56139 (8)	0.77971 (9)	0.0184 (2)
C10	0.54693 (14)	0.67709 (9)	0.90914 (10)	0.0237 (3)
H10A	0.5729	0.7248	0.9551	0.028*
C11	0.43667 (13)	0.62292 (8)	0.90605 (9)	0.0197 (2)
C12	0.34425 (13)	0.62715 (9)	0.97466 (9)	0.0206 (3)
C13	0.31678 (15)	0.71102 (10)	1.00913 (11)	0.0265 (3)
H13A	0.3513	0.7630	0.9843	0.032*
C14	0.23944 (16)	0.71898 (11)	1.07930 (11)	0.0317 (3)
H14A	0.2232	0.7761	1.1036	0.038*
C15	0.18594 (17)	0.64354 (11)	1.11381 (12)	0.0331 (3)
H15A	0.1326	0.6489	1.1616	0.040*
C16	0.21014 (16)	0.56054 (11)	1.07879 (11)	0.0306 (3)
H16A	0.1716	0.5091	1.1016	0.037*
C17	0.29047 (15)	0.55166 (9)	1.01040 (10)	0.0247 (3)
H17A	0.3087	0.4942	0.9880	0.030*
C18	0.30424 (13)	0.49851 (8)	0.79994 (9)	0.0180 (2)
C19	0.32421 (14)	0.40723 (9)	0.80007 (10)	0.0218 (3)
H19A	0.4162	0.3828	0.8251	0.026*
C20	0.20894 (16)	0.35139 (9)	0.76347 (11)	0.0252 (3)
H20A	0.2219	0.2887	0.7618	0.030*
C21	0.07491 (15)	0.38805 (9)	0.72938 (10)	0.0254 (3)
H21A	−0.0038	0.3498	0.7047	0.031*
C22	0.05328 (14)	0.47927 (9)	0.73060 (10)	0.0223 (3)
H22A	−0.0395	0.5032	0.7086	0.027*
C23	0.16958 (13)	0.53563 (8)	0.76461 (9)	0.0182 (2)
C24	0.02588 (16)	0.66550 (10)	0.73440 (16)	0.0415 (4)
H24A	−0.0176	0.6510	0.6645	0.062*
H24B	0.0344	0.7303	0.7422	0.062*
H24C	−0.0334	0.6423	0.7757	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01853 (16)	0.02102 (16)	0.02916 (18)	−0.00347 (11)	0.00855 (13)	−0.00330 (12)
O1	0.0212 (5)	0.0285 (5)	0.0302 (5)	−0.0048 (4)	0.0112 (4)	−0.0021 (4)
O2	0.0164 (4)	0.0192 (4)	0.0274 (5)	0.0005 (3)	0.0045 (4)	0.0000 (4)
N1	0.0162 (5)	0.0221 (5)	0.0212 (5)	−0.0002 (4)	0.0064 (4)	−0.0009 (4)
N2	0.0153 (5)	0.0183 (5)	0.0199 (5)	−0.0009 (4)	0.0053 (4)	−0.0015 (4)
C1	0.0174 (6)	0.0235 (6)	0.0197 (6)	0.0018 (5)	0.0049 (5)	0.0030 (5)
C2	0.0167 (6)	0.0278 (6)	0.0192 (6)	0.0047 (5)	0.0041 (5)	0.0001 (5)
C3	0.0260 (7)	0.0278 (7)	0.0252 (7)	0.0022 (5)	0.0085 (5)	−0.0014 (5)
C4	0.0310 (7)	0.0269 (7)	0.0307 (7)	0.0045 (6)	0.0051 (6)	−0.0015 (6)
C5	0.0324 (8)	0.0340 (8)	0.0263 (7)	0.0113 (6)	0.0039 (6)	−0.0068 (6)
C6	0.0277 (7)	0.0432 (8)	0.0209 (7)	0.0085 (6)	0.0081 (6)	−0.0014 (6)
C7	0.0180 (6)	0.0352 (7)	0.0191 (6)	0.0048 (5)	0.0040 (5)	0.0018 (5)
C8	0.0310 (8)	0.0423 (8)	0.0227 (7)	−0.0043 (6)	0.0108 (6)	0.0020 (6)
C9	0.0149 (5)	0.0196 (6)	0.0203 (6)	0.0003 (4)	0.0036 (5)	0.0016 (5)
C10	0.0215 (6)	0.0227 (6)	0.0273 (7)	−0.0009 (5)	0.0071 (5)	−0.0060 (5)
C11	0.0188 (6)	0.0201 (6)	0.0192 (6)	0.0023 (5)	0.0034 (5)	−0.0016 (5)
C12	0.0173 (6)	0.0261 (6)	0.0171 (6)	0.0025 (5)	0.0023 (5)	−0.0024 (5)
C13	0.0239 (7)	0.0267 (7)	0.0294 (7)	0.0000 (5)	0.0079 (6)	−0.0057 (5)
C14	0.0297 (7)	0.0349 (8)	0.0318 (8)	0.0049 (6)	0.0105 (6)	−0.0110 (6)
C15	0.0308 (8)	0.0453 (9)	0.0266 (7)	0.0087 (7)	0.0138 (6)	−0.0007 (6)
C16	0.0323 (8)	0.0359 (8)	0.0260 (7)	0.0055 (6)	0.0118 (6)	0.0072 (6)
C17	0.0261 (7)	0.0265 (7)	0.0218 (6)	0.0053 (5)	0.0067 (5)	0.0012 (5)
C18	0.0174 (6)	0.0209 (6)	0.0169 (6)	−0.0031 (5)	0.0069 (5)	−0.0012 (4)
C19	0.0234 (6)	0.0220 (6)	0.0221 (6)	0.0009 (5)	0.0101 (5)	0.0011 (5)
C20	0.0327 (7)	0.0184 (6)	0.0289 (7)	−0.0034 (5)	0.0159 (6)	−0.0015 (5)
C21	0.0259 (7)	0.0266 (7)	0.0271 (7)	−0.0098 (5)	0.0129 (6)	−0.0064 (5)
C22	0.0181 (6)	0.0267 (6)	0.0236 (6)	−0.0034 (5)	0.0080 (5)	−0.0027 (5)
C23	0.0195 (6)	0.0199 (6)	0.0169 (6)	−0.0017 (5)	0.0077 (5)	−0.0005 (4)
C24	0.0209 (7)	0.0249 (7)	0.0752 (13)	0.0040 (6)	0.0063 (8)	−0.0046 (8)

Geometric parameters (Å, º) top

S1—C10	1.7337 (14)	C10—H10A	0.9500
S1—C9	1.7449 (13)	C11—C12	1.4774 (17)
O1—C1	1.2347 (16)	C12—C17	1.3943 (19)
O2—C23	1.3587 (15)	C12—C13	1.3980 (18)
O2—C24	1.4248 (17)	C13—C14	1.3875 (19)
N1—C9	1.3032 (17)	C13—H13A	0.9500
N1—C1	1.3720 (16)	C14—C15	1.385 (2)
N2—C9	1.3730 (16)	C14—H14A	0.9500
N2—C11	1.4039 (16)	C15—C16	1.381 (2)
N2—C18	1.4373 (16)	C15—H15A	0.9500
C1—C2	1.4978 (18)	C16—C17	1.3896 (19)
C2—C3	1.3991 (19)	C16—H16A	0.9500
C2—C7	1.4073 (18)	C17—H17A	0.9500
C3—C4	1.382 (2)	C18—C19	1.3840 (18)
C3—H3A	0.9500	C18—C23	1.3965 (18)
C4—C5	1.384 (2)	C19—C20	1.3909 (19)
C4—H4A	0.9500	C19—H19A	0.9500
C5—C6	1.377 (2)	C20—C21	1.387 (2)
C5—H5A	0.9500	C20—H20A	0.9500
C6—C7	1.403 (2)	C21—C22	1.386 (2)
C6—H6A	0.9500	C21—H21A	0.9500
C7—C8	1.502 (2)	C22—C23	1.3978 (18)
C8—H8A	0.9800	C22—H22A	0.9500
C8—H8B	0.9800	C24—H24A	0.9800
C8—H8C	0.9800	C24—H24B	0.9800
C10—C11	1.3425 (18)	C24—H24C	0.9800

C10—S1—C9	90.48 (6)	C17—C12—C13	119.04 (12)
C23—O2—C24	117.19 (11)	C17—C12—C11	123.15 (12)
C9—N1—C1	116.67 (11)	C13—C12—C11	117.71 (12)
C9—N2—C11	114.60 (10)	C14—C13—C12	120.51 (14)
C9—N2—C18	119.83 (10)	C14—C13—H13A	119.7
C11—N2—C18	124.97 (10)	C12—C13—H13A	119.7
O1—C1—N1	124.08 (12)	C15—C14—C13	119.89 (14)
O1—C1—C2	121.99 (11)	C15—C14—H14A	120.1
N1—C1—C2	113.90 (11)	C13—C14—H14A	120.1
C3—C2—C7	119.77 (13)	C16—C15—C14	120.03 (13)
C3—C2—C1	117.61 (12)	C16—C15—H15A	120.0
C7—C2—C1	122.61 (12)	C14—C15—H15A	120.0
C4—C3—C2	121.52 (13)	C15—C16—C17	120.52 (14)
C4—C3—H3A	119.2	C15—C16—H16A	119.7
C2—C3—H3A	119.2	C17—C16—H16A	119.7
C3—C4—C5	118.94 (14)	C16—C17—C12	119.97 (13)
C3—C4—H4A	120.5	C16—C17—H17A	120.0
C5—C4—H4A	120.5	C12—C17—H17A	120.0
C6—C5—C4	120.24 (13)	C19—C18—C23	121.02 (12)
C6—C5—H5A	119.9	C19—C18—N2	120.54 (11)
C4—C5—H5A	119.9	C23—C18—N2	118.38 (11)
C5—C6—C7	122.17 (13)	C18—C19—C20	119.70 (13)
C5—C6—H6A	118.9	C18—C19—H19A	120.2
C7—C6—H6A	118.9	C20—C19—H19A	120.2
C6—C7—C2	117.34 (13)	C21—C20—C19	119.36 (12)
C6—C7—C8	118.64 (13)	C21—C20—H20A	120.3
C2—C7—C8	123.96 (13)	C19—C20—H20A	120.3
C7—C8—H8A	109.5	C22—C21—C20	121.43 (12)
C7—C8—H8B	109.5	C22—C21—H21A	119.3
H8A—C8—H8B	109.5	C20—C21—H21A	119.3
C7—C8—H8C	109.5	C21—C22—C23	119.25 (13)
H8A—C8—H8C	109.5	C21—C22—H22A	120.4
H8B—C8—H8C	109.5	C23—C22—H22A	120.4
N1—C9—N2	121.26 (11)	O2—C23—C18	116.08 (11)
N1—C9—S1	128.79 (10)	O2—C23—C22	124.72 (12)
N2—C9—S1	109.95 (9)	C18—C23—C22	119.19 (12)
C11—C10—S1	113.32 (10)	O2—C24—H24A	109.5
C11—C10—H10A	123.3	O2—C24—H24B	109.5
S1—C10—H10A	123.3	H24A—C24—H24B	109.5
C10—C11—N2	111.61 (11)	O2—C24—H24C	109.5
C10—C11—C12	125.11 (12)	H24A—C24—H24C	109.5
N2—C11—C12	123.21 (11)	H24B—C24—H24C	109.5

C9—N1—C1—O1	−3.59 (19)	C18—N2—C11—C12	12.82 (19)
C9—N1—C1—C2	174.37 (11)	C10—C11—C12—C17	−142.16 (15)
O1—C1—C2—C3	152.58 (13)	N2—C11—C12—C17	34.49 (19)
N1—C1—C2—C3	−25.43 (17)	C10—C11—C12—C13	34.2 (2)
O1—C1—C2—C7	−26.54 (19)	N2—C11—C12—C13	−149.19 (13)
N1—C1—C2—C7	155.46 (12)	C17—C12—C13—C14	1.2 (2)
C7—C2—C3—C4	0.3 (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—C16	0.3 (2)
C3—C4—C5—C6	0.9 (2)	C14—C15—C16—C17	1.3 (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—C16	0.4 (2)
C5—C6—C7—C8	−177.96 (14)	C11—C12—C17—C16	176.67 (13)
C3—C2—C7—C6	0.48 (19)	C9—N2—C18—C19	63.62 (16)
C1—C2—C7—C6	179.58 (12)	C11—N2—C18—C19	−125.79 (13)
C3—C2—C7—C8	177.79 (13)	C9—N2—C18—C23	−113.51 (13)
C1—C2—C7—C8	−3.1 (2)	C11—N2—C18—C23	57.08 (17)
C1—N1—C9—N2	−178.30 (11)	C23—C18—C19—C20	0.75 (19)
C1—N1—C9—S1	1.15 (18)	N2—C18—C19—C20	−176.30 (11)
C11—N2—C9—N1	177.57 (11)	C18—C19—C20—C21	−1.45 (19)
C18—N2—C9—N1	−10.90 (18)	C19—C20—C21—C22	0.3 (2)
C11—N2—C9—S1	−1.97 (13)	C20—C21—C22—C23	1.6 (2)
C18—N2—C9—S1	169.55 (9)	C24—O2—C23—C18	−176.49 (13)
C10—S1—C9—N1	−177.59 (13)	C24—O2—C23—C22	4.66 (19)
C10—S1—C9—N2	1.91 (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—N2	0.64 (15)	C19—C18—C23—C22	1.13 (18)
S1—C10—C11—C12	177.62 (10)	N2—C18—C23—C22	178.25 (11)
C9—N2—C11—C10	0.89 (16)	C21—C22—C23—O2	176.52 (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, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···N1	0.95	2.42	2.7572 (18)	101
C14—H14A···O1ⁱ	0.95	2.52	3.4635 (19)	171
C22—H22A···O1ⁱⁱ	0.95	2.48	3.4240 (18)	170

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₀N₂O₂S
M_r	400.48
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	153
a, b, c (Å)	9.7826 (18), 15.010 (3), 13.917 (3)
β (°)	105.092 (4)
V (Å³)	1973.1 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.50 × 0.40 × 0.25

Data collection
Diffractometer	Bruker AXS SMART APEX
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.912, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	16940, 4697, 4150
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.102, 1.04
No. of reflections	4697
No. of parameters	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.21

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT, SHELXTL (Bruker, 2002), SHELXTL.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···N1	0.95	2.42	2.7572 (18)	100.6
C14—H14A···O1ⁱ	0.95	2.52	3.4635 (19)	170.7
C22—H22A···O1ⁱⁱ	0.95	2.48	3.4240 (18)	170.1

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

Acknowledgements

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

References

Arcadi, A., Attanasi, O. A., Giorgi, G., Filippone, P., Rossi, E. & Santeusanio, S. (2003). Tetrahedron Lett. 44, 8391–8394. Web of Science CSD CrossRef CAS Google Scholar
Bonde, C. G. & Gaikwad, N. J. J. (2004). Bioorg. Med. Chem. 12, 2151–1254. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2002). SMART (Version 5.62), SAINT (Version 6.02), SHELXTL (Version 6.10) and SADABS (Version 2.03). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kim, D. S., Jeong, Y. M., Park, I. K., Hahn, H.-G. & Lee, H.-K. (2007). Biol. Pharm. Bull. 30, 180–184. Web of Science CrossRef PubMed CAS Google Scholar
Lee, C. L. & Sim, M. M. (2000). Tetrahedron Lett. 41, 5729–5732. Web of Science CrossRef CAS Google Scholar
Saeed, A. & Parvez, M. (2006). J. Heterocycl. Chem. 43, 1027–1030. CrossRef CAS Google Scholar
Shehata, I. A., Elsubbagh, H. I., Abdelal, A. M., Elsherbeny, M. A. & Alobaid, A. A. (1996). Med. Chem. Res. 6, 148–151. CAS Google Scholar
Venkatachalan, T. K., Sudbeck, E. A., Mao, C. & Uckun, F. M. (2001). Bioorg. Med. Chem. Lett. 11, 523–528. Web of Science PubMed Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o66

https://doi.org/10.1107/S1600536807062290

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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