(Z)-N-[3-(2-Methoxy-phen-yl)-4-phenyl-2,3-dihydro-thia-zol-2-yl-idene]-2-methyl-benzamide.

In the title mol-ecule, C(24)H(20)N(2)O(2)S, the thia-zole and amide groups are essentially coplanar. The thia-zole ring forms dihedral angles of 61.62 (4) and 26.75 (5)° with the benzene rings of the methoxy-phenyl and methyl-phenyl groups, respectively, and 33.69 (6)° with the phenyl ring. The crystal packing is stabilized by inter-molecular 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 = 400.48

Monoclinic,

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[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 ▶); 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.

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

C24H20N2O2S	F000 = 840
Mr = 400.48	Dx = 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 = 2.6–28.3º
b = 15.010 (3) Å	µ = 0.19 mm−1
c = 13.917 (3) Å	T = 153 (2) K
β = 105.092 (4)º	Prism, colourless
V = 1973.1 (6) Å3	0.50 × 0.40 × 0.25 mm
Z = 4

Bruker AXS SMART APEX diffractometer	4697 independent reflections
Radiation source: sealed tube	4150 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.025
T = 153(2) K	θmax = 27.9º
φ and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Bruker, 2002)	h = −11→12
Tmin = 0.912, Tmax = 0.955	k = −19→19
16940 measured reflections	l = −18→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038	H-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 reflections	Δρmax = 0.34 e Å−3
264 parameters	Δρmin = −0.21 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .