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

Geometric parameters of the title compound, C(24)H(20)N(2)O(2)S, 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 methoxy-phenyl ring, respectively.

Related literature

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

Experimental

Crystal data

C24H20N2O2S

M = 400.48

Monoclinic,

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 ▶; Blessing, 1995 ▶) 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 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

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

C24H20N2O2S	F000 = 840
Mr = 400.48	Dx = 1.329 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10726 reflections
a = 10.1305 (10) Å	θ = 3.8–25.8º
b = 20.0583 (14) Å	µ = 0.19 mm−1
c = 10.0959 (10) Å	T = 173 (2) K
β = 102.710 (8)º	Block, colourless
V = 2001.2 (3) Å3	0.33 × 0.23 × 0.22 mm
Z = 4

Stoe IPDSII two-circle diffractometer	3728 independent reflections
Radiation source: fine-focus sealed tube	3095 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.039
T = 173(2) K	θmax = 25.6º
ω scans	θmin = 3.7º
Absorption correction: multi-scan(MULABS; Spek, 2003; Blessing, 1995)	h = −12→11
Tmin = 0.942, Tmax = 0.951	k = −21→24
11964 measured reflections	l = −12→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H-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 reflections	Δρmax = 0.15 e Å−3
264 parameters	Δρmin = −0.28 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	0.98050 (4)	0.70737 (2)	0.51355 (5)	0.04086 (15)
O1	1.10348 (11)	0.68440 (6)	0.31286 (12)	0.0397 (3)
O2	0.72991 (11)	0.52503 (5)	0.53280 (10)	0.0332 (3)
N1	0.75221 (12)	0.64830 (6)	0.43148 (12)	0.0265 (3)
N2	0.89232 (13)	0.63407 (6)	0.27787 (12)	0.0295 (3)
C1	0.87220 (15)	0.65906 (7)	0.39275 (15)	0.0281 (3)
C2	0.74474 (16)	0.67752 (8)	0.55719 (15)	0.0305 (3)
C3	0.86066 (19)	0.70950 (9)	0.61315 (18)	0.0434 (4)
H3	0.8755	0.7311	0.6989	0.052*
C4	1.01248 (15)	0.64968 (7)	0.24281 (15)	0.0303 (3)
C11	1.02529 (15)	0.62264 (8)	0.10802 (15)	0.0301 (3)
C12	0.91665 (16)	0.59116 (8)	0.02041 (16)	0.0347 (4)
H12	0.8335	0.5851	0.0478	0.042*
C13	0.92970 (18)	0.56869 (9)	−0.10637 (17)	0.0396 (4)
H13	0.8548	0.5478	−0.1649	0.047*
C14	1.05099 (17)	0.57628 (9)	−0.14929 (16)	0.0354 (4)
C15	1.15848 (17)	0.60780 (10)	−0.06097 (17)	0.0397 (4)
H15	1.2418	0.6135	−0.0881	0.048*
C16	1.14651 (16)	0.63095 (9)	0.06546 (17)	0.0372 (4)
H16	1.2210	0.6525	0.1232	0.045*
C17	1.0679 (2)	0.54980 (10)	−0.28494 (17)	0.0462 (4)
H17A	1.0897	0.5022	−0.2767	0.069*
H17B	1.1415	0.5738	−0.3130	0.069*
H17C	0.9836	0.5563	−0.3530	0.069*
C21	0.65588 (14)	0.60120 (7)	0.35548 (14)	0.0254 (3)
C22	0.64954 (14)	0.53698 (7)	0.40723 (14)	0.0259 (3)
C23	0.56515 (16)	0.48964 (8)	0.32885 (15)	0.0329 (4)
H23	0.5586	0.4459	0.3629	0.040*
C24	0.49103 (17)	0.50720 (9)	0.20088 (16)	0.0379 (4)
H24	0.4345	0.4749	0.1473	0.045*
C25	0.49813 (17)	0.57099 (9)	0.14992 (16)	0.0387 (4)
H25	0.4464	0.5822	0.0624	0.046*
C26	0.58140 (16)	0.61869 (8)	0.22749 (14)	0.0326 (4)
H26	0.5871	0.6625	0.1933	0.039*
C27	0.74026 (19)	0.45719 (8)	0.58037 (16)	0.0369 (4)
H27A	0.6506	0.4411	0.5872	0.055*
H27B	0.8019	0.4551	0.6699	0.055*
H27C	0.7753	0.4291	0.5164	0.055*
C31	0.62025 (16)	0.67828 (7)	0.61048 (15)	0.0297 (3)
C32	0.63140 (18)	0.67578 (8)	0.75194 (15)	0.0358 (4)
H32	0.7170	0.6677	0.8107	0.043*
C33	0.5178 (2)	0.68500 (8)	0.80611 (17)	0.0415 (4)
H33	0.5264	0.6827	0.9016	0.050*
C34	0.3918 (2)	0.69747 (9)	0.72213 (18)	0.0414 (4)
H34	0.3151	0.7050	0.7600	0.050*
C35	0.37924 (18)	0.69885 (8)	0.58204 (17)	0.0367 (4)
H35	0.2933	0.7068	0.5238	0.044*
C36	0.49179 (16)	0.68870 (7)	0.52706 (15)	0.0313 (3)
H36	0.4815	0.6888	0.4312	0.038*

	U11	U22	U33	U12	U13	U23
S1	0.0358 (2)	0.0385 (3)	0.0506 (3)	−0.01358 (18)	0.01446 (18)	−0.01702 (18)
O1	0.0342 (6)	0.0394 (7)	0.0465 (7)	−0.0054 (5)	0.0112 (5)	−0.0059 (5)
O2	0.0418 (6)	0.0246 (5)	0.0292 (5)	−0.0013 (5)	−0.0009 (5)	0.0015 (4)
N1	0.0299 (6)	0.0224 (6)	0.0278 (6)	−0.0030 (5)	0.0074 (5)	−0.0025 (5)
N2	0.0315 (7)	0.0266 (6)	0.0318 (6)	0.0011 (5)	0.0098 (5)	0.0012 (5)
C1	0.0300 (8)	0.0209 (7)	0.0335 (7)	0.0003 (6)	0.0075 (6)	0.0014 (6)
C2	0.0381 (8)	0.0246 (7)	0.0301 (7)	−0.0034 (7)	0.0102 (6)	−0.0061 (6)
C3	0.0458 (10)	0.0424 (10)	0.0444 (9)	−0.0146 (8)	0.0153 (8)	−0.0194 (8)
C4	0.0290 (8)	0.0249 (8)	0.0377 (8)	0.0040 (6)	0.0089 (6)	0.0051 (6)
C11	0.0295 (8)	0.0274 (8)	0.0347 (8)	0.0062 (6)	0.0098 (6)	0.0071 (6)
C12	0.0290 (8)	0.0376 (9)	0.0402 (9)	0.0020 (7)	0.0131 (6)	−0.0002 (7)
C13	0.0342 (9)	0.0455 (10)	0.0393 (9)	0.0014 (7)	0.0088 (7)	−0.0037 (7)
C14	0.0354 (8)	0.0383 (9)	0.0344 (8)	0.0095 (7)	0.0120 (7)	0.0077 (7)
C15	0.0326 (8)	0.0507 (11)	0.0392 (9)	0.0038 (8)	0.0155 (7)	0.0099 (7)
C16	0.0298 (8)	0.0444 (10)	0.0382 (8)	0.0011 (7)	0.0090 (7)	0.0071 (7)
C17	0.0479 (10)	0.0561 (12)	0.0390 (9)	0.0069 (9)	0.0192 (8)	0.0026 (8)
C21	0.0251 (7)	0.0268 (7)	0.0249 (7)	−0.0006 (6)	0.0065 (5)	−0.0047 (5)
C22	0.0259 (7)	0.0269 (8)	0.0252 (7)	0.0000 (6)	0.0062 (6)	−0.0033 (5)
C23	0.0337 (8)	0.0296 (8)	0.0367 (8)	−0.0051 (7)	0.0103 (7)	−0.0074 (6)
C24	0.0332 (9)	0.0449 (10)	0.0342 (8)	−0.0064 (7)	0.0049 (7)	−0.0146 (7)
C25	0.0347 (9)	0.0527 (11)	0.0261 (7)	0.0031 (8)	0.0007 (6)	−0.0055 (7)
C26	0.0350 (8)	0.0357 (9)	0.0269 (7)	0.0044 (7)	0.0065 (6)	0.0011 (6)
C27	0.0517 (10)	0.0259 (8)	0.0336 (8)	0.0036 (7)	0.0102 (7)	0.0035 (6)
C31	0.0389 (8)	0.0202 (7)	0.0319 (7)	−0.0040 (6)	0.0118 (6)	−0.0053 (6)
C32	0.0468 (10)	0.0290 (8)	0.0317 (8)	−0.0007 (7)	0.0091 (7)	−0.0047 (6)
C33	0.0645 (12)	0.0316 (9)	0.0333 (8)	−0.0023 (8)	0.0212 (8)	−0.0042 (7)
C34	0.0509 (10)	0.0318 (9)	0.0492 (10)	−0.0048 (8)	0.0277 (8)	−0.0057 (7)
C35	0.0385 (9)	0.0293 (8)	0.0443 (9)	−0.0025 (7)	0.0134 (7)	−0.0043 (7)
C36	0.0410 (9)	0.0233 (7)	0.0311 (8)	−0.0030 (7)	0.0110 (6)	−0.0025 (6)

S1—C3	1.7390 (19)	C17—H17B	0.9800
S1—C1	1.7439 (15)	C17—H17C	0.9800
O1—C4	1.2442 (19)	C21—C26	1.3903 (19)
O2—C22	1.3687 (17)	C21—C22	1.397 (2)
O2—C27	1.4392 (18)	C22—C23	1.400 (2)
N1—C1	1.373 (2)	C23—C24	1.389 (2)
N1—C2	1.4151 (19)	C23—H23	0.9500
N1—C21	1.4505 (17)	C24—C25	1.387 (3)
N2—C1	1.320 (2)	C24—H24	0.9500
N2—C4	1.376 (2)	C25—C26	1.396 (2)
C2—C3	1.348 (2)	C25—H25	0.9500
C2—C31	1.476 (2)	C26—H26	0.9500
C3—H3	0.9500	C27—H27A	0.9800
C4—C11	1.497 (2)	C27—H27B	0.9800
C11—C16	1.397 (2)	C27—H27C	0.9800
C11—C12	1.401 (2)	C31—C36	1.402 (2)
C12—C13	1.390 (2)	C31—C32	1.409 (2)
C12—H12	0.9500	C32—C33	1.390 (2)
C13—C14	1.398 (2)	C32—H32	0.9500
C13—H13	0.9500	C33—C34	1.391 (3)
C14—C15	1.398 (2)	C33—H33	0.9500
C14—C17	1.514 (2)	C34—C35	1.392 (2)
C15—C16	1.388 (2)	C34—H34	0.9500
C15—H15	0.9500	C35—C36	1.388 (2)
C16—H16	0.9500	C35—H35	0.9500
C17—H17A	0.9800	C36—H36	0.9500
C3—S1—C1	90.36 (8)	C26—C21—C22	121.34 (13)
C22—O2—C27	117.35 (11)	C26—C21—N1	119.45 (14)
C1—N1—C2	114.55 (12)	C22—C21—N1	118.93 (12)
C1—N1—C21	119.11 (12)	O2—C22—C21	116.16 (12)
C2—N1—C21	125.57 (13)	O2—C22—C23	124.72 (14)
C1—N2—C4	117.12 (13)	C21—C22—C23	119.12 (13)
N2—C1—N1	120.52 (13)	C24—C23—C22	119.43 (15)
N2—C1—S1	129.09 (12)	C24—C23—H23	120.3
N1—C1—S1	110.39 (10)	C22—C23—H23	120.3
C3—C2—N1	111.07 (14)	C25—C24—C23	121.16 (14)
C3—C2—C31	125.28 (14)	C25—C24—H24	119.4
N1—C2—C31	123.35 (13)	C23—C24—H24	119.4
C2—C3—S1	113.61 (12)	C24—C25—C26	119.89 (14)
C2—C3—H3	123.2	C24—C25—H25	120.1
S1—C3—H3	123.2	C26—C25—H25	120.1
O1—C4—N2	124.59 (15)	C21—C26—C25	119.06 (15)
O1—C4—C11	121.19 (15)	C21—C26—H26	120.5
N2—C4—C11	114.19 (13)	C25—C26—H26	120.5
C16—C11—C12	118.75 (15)	O2—C27—H27A	109.5
C16—C11—C4	119.62 (14)	O2—C27—H27B	109.5
C12—C11—C4	121.59 (14)	H27A—C27—H27B	109.5
C13—C12—C11	120.43 (16)	O2—C27—H27C	109.5
C13—C12—H12	119.8	H27A—C27—H27C	109.5
C11—C12—H12	119.8	H27B—C27—H27C	109.5
C12—C13—C14	121.20 (16)	C36—C31—C32	118.12 (15)
C12—C13—H13	119.4	C36—C31—C2	122.50 (13)
C14—C13—H13	119.4	C32—C31—C2	119.00 (14)
C15—C14—C13	117.78 (15)	C33—C32—C31	120.35 (15)
C15—C14—C17	120.57 (16)	C33—C32—H32	119.8
C13—C14—C17	121.64 (16)	C31—C32—H32	119.8
C16—C15—C14	121.64 (16)	C32—C33—C34	120.80 (15)
C16—C15—H15	119.2	C32—C33—H33	119.6
C14—C15—H15	119.2	C34—C33—H33	119.6
C15—C16—C11	120.21 (15)	C33—C34—C35	119.30 (17)
C15—C16—H16	119.9	C33—C34—H34	120.4
C11—C16—H16	119.9	C35—C34—H34	120.4
C14—C17—H17A	109.5	C36—C35—C34	120.24 (16)
C14—C17—H17B	109.5	C36—C35—H35	119.9
H17A—C17—H17B	109.5	C34—C35—H35	119.9
C14—C17—H17C	109.5	C35—C36—C31	121.14 (14)
H17A—C17—H17C	109.5	C35—C36—H36	119.4
H17B—C17—H17C	109.5	C31—C36—H36	119.4
C4—N2—C1—N1	176.95 (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—N2	179.56 (13)	C2—N1—C21—C26	116.67 (16)
C21—N1—C1—N2	9.1 (2)	C1—N1—C21—C22	99.99 (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—C23	7.6 (2)
C3—S1—C1—N1	1.21 (12)	C26—C21—C22—O2	178.36 (13)
C1—N1—C2—C3	−0.81 (19)	N1—C21—C22—O2	4.5 (2)
C21—N1—C2—C3	168.98 (15)	C26—C21—C22—C23	−0.7 (2)
C1—N1—C2—C31	173.17 (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—S1	1.76 (19)	C21—C22—C23—C24	0.8 (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—C26	0.3 (3)
C1—N2—C4—O1	1.4 (2)	C22—C21—C26—C25	0.4 (2)
C1—N2—C4—C11	−176.94 (12)	N1—C21—C26—C25	174.20 (14)
O1—C4—C11—C16	6.2 (2)	C24—C25—C26—C21	−0.2 (2)
N2—C4—C11—C16	−175.35 (13)	C3—C2—C31—C36	134.02 (18)
O1—C4—C11—C12	−171.36 (15)	N1—C2—C31—C36	−39.1 (2)
N2—C4—C11—C12	7.1 (2)	C3—C2—C31—C32	−38.8 (2)
C16—C11—C12—C13	0.0 (2)	N1—C2—C31—C32	148.05 (15)
C4—C11—C12—C13	177.59 (15)	C36—C31—C32—C33	−1.4 (2)
C11—C12—C13—C14	0.6 (3)	C2—C31—C32—C33	171.72 (14)
C12—C13—C14—C15	−0.6 (3)	C31—C32—C33—C34	−0.6 (3)
C12—C13—C14—C17	177.76 (16)	C32—C33—C34—C35	1.8 (3)
C13—C14—C15—C16	0.1 (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—C11	0.5 (3)	C32—C31—C36—C35	2.4 (2)
C12—C11—C16—C15	−0.5 (2)	C2—C31—C36—C35	−170.49 (14)