(Z)-2-(5-Acetyl-4-methyl-3-phenyl-2,3-dihydro-1,3-thia-zol-2-yl-idene)-3-(3-methyl-1-benzofuran-2-yl)-3-oxo-propane-nitrile.

In the title compound, C(24)H(18)N(2)O(3)S, the benzofuran ring system (r.m.s. deviation = 0.010 Å) forms dihedral angles of 83.13 (17) and 8.92 (14)° with the benzene and thia-zole rings, respectively. The dihedral angle between the benzene and thia-zole rings is 84.51 (19)°. The mol-ecular structure features an intra-molecular C-H⋯O hydrogen bond, which closes an S(6) ring. There are no inter-molecular hydrogen bonds observed in this structure.

Related literature

For background to and the biological activity of benzofuran derivatives, see: Abdel-Aziz et al. (2009) ▶; Abdel-Wahab et al. (2009 ▶). For further synthetic details, see: Dawood et al. (2005 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Fun et al. (2012 ▶); Abdel-Aziz et al. (2012 ▶).

Experimental

Crystal data

C24H18N2O3S

M = 414.46

Monoclinic,

a = 9.7836 (4) Å

b = 6.3682 (3) Å

c = 16.2330 (6) Å

β = 100.351 (3)°

V = 994.92 (7) Å3

Z = 2

Cu Kα radiation

μ = 1.69 mm−1

T = 296 K

0.92 × 0.09 × 0.06 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.306, T max = 0.906

7151 measured reflections

2831 independent reflections

2310 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.119

S = 1.01

2831 reflections

275 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.32 e Å−3

Absolute structure: Flack (1983 ▶), 831 Friedel pairs

Flack parameter: 0.03 (3)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL ; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812035039/hb6913sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035039/hb6913Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035039/hb6913Isup3.cml

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

C24H18N2O3S	F(000) = 432
Mr = 414.46	Dx = 1.383 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2yb	Cell parameters from 1283 reflections
a = 9.7836 (4) Å	θ = 2.8–65.0°
b = 6.3682 (3) Å	µ = 1.69 mm−1
c = 16.2330 (6) Å	T = 296 K
β = 100.351 (3)°	Needle, yellow
V = 994.92 (7) Å3	0.92 × 0.09 × 0.06 mm
Z = 2

Bruker SMART APEXII CCD diffractometer	2831 independent reflections
Radiation source: fine-focus sealed tube	2310 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
φ and ω scans	θmax = 69.8°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.306, Tmax = 0.906	k = −6→7
7151 measured reflections	l = −19→19

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0714P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
2831 reflections	Δρmax = 0.25 e Å−3
275 parameters	Δρmin = −0.32 e Å−3
1 restraint	Absolute structure: Flack (1983), 831 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (3)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.23468 (9)	0.89038 (14)	0.13562 (4)	0.0454 (2)
N1	0.1798 (2)	0.8805 (5)	0.28286 (14)	0.0386 (6)
N2	0.3568 (3)	0.4048 (7)	0.39528 (18)	0.0667 (9)
O1	0.4965 (2)	0.1891 (4)	0.26849 (14)	0.0482 (6)
O2	0.3871 (3)	0.5930 (5)	0.11922 (15)	0.0618 (8)
O3	−0.0119 (3)	1.3800 (6)	0.12668 (17)	0.0857 (11)
C1	0.4888 (4)	0.3163 (6)	0.1977 (2)	0.0452 (8)
C2	0.5710 (4)	0.2416 (6)	0.1451 (2)	0.0454 (8)
C3	0.6340 (3)	0.0518 (6)	0.1842 (2)	0.0462 (9)
C4	0.7255 (4)	−0.0986 (8)	0.1629 (2)	0.0600 (10)
H4A	0.7602	−0.0871	0.1134	0.072*
C5	0.7627 (4)	−0.2620 (7)	0.2159 (3)	0.0659 (12)
H5A	0.8227	−0.3641	0.2020	0.079*
C6	0.7126 (4)	−0.2797 (7)	0.2907 (3)	0.0615 (11)
H6A	0.7400	−0.3935	0.3258	0.074*
C7	0.6235 (3)	−0.1329 (7)	0.3142 (2)	0.0542 (9)
H7A	0.5910	−0.1428	0.3645	0.065*
C8	0.5854 (3)	0.0286 (6)	0.2590 (2)	0.0446 (8)
C9	0.4003 (4)	0.5035 (6)	0.1875 (2)	0.0453 (8)
C10	0.3304 (3)	0.5853 (6)	0.2518 (2)	0.0398 (7)
C11	0.2520 (3)	0.7699 (5)	0.23210 (18)	0.0366 (7)
C12	0.1271 (4)	1.0842 (6)	0.1664 (2)	0.0440 (8)
C13	0.1085 (3)	1.0533 (6)	0.2467 (2)	0.0421 (8)
C14	0.0248 (4)	1.1810 (7)	0.2967 (2)	0.0532 (10)
H14A	−0.0085	1.3050	0.2659	0.080*
H14B	0.0819	1.2204	0.3489	0.080*
H14C	−0.0527	1.0996	0.3075	0.080*
C15	0.0719 (4)	1.2547 (6)	0.1092 (2)	0.0514 (9)
C16	0.1266 (4)	1.2735 (7)	0.0292 (2)	0.0591 (11)
H16A	0.1020	1.4083	0.0044	0.089*
H16B	0.0871	1.1649	−0.0087	0.089*
H16C	0.2259	1.2593	0.0406	0.089*
C17	0.3444 (3)	0.4875 (6)	0.3318 (2)	0.0446 (8)
C18	0.1851 (3)	0.8306 (5)	0.37089 (19)	0.0377 (7)
C19	0.0806 (4)	0.7114 (6)	0.3935 (2)	0.0488 (8)
H19A	0.0069	0.6639	0.3535	0.059*
C20	0.0879 (5)	0.6641 (7)	0.4774 (3)	0.0629 (11)
H20A	0.0178	0.5853	0.4943	0.076*
C21	0.1971 (5)	0.7323 (9)	0.5355 (2)	0.0687 (13)
H21A	0.2022	0.6964	0.5915	0.082*
C22	0.2995 (4)	0.8532 (8)	0.5121 (2)	0.0669 (13)
H22A	0.3730	0.9003	0.5524	0.080*
C23	0.2939 (3)	0.9058 (7)	0.4283 (2)	0.0496 (9)
H23A	0.3621	0.9895	0.4118	0.059*
C24	0.5966 (5)	0.3262 (8)	0.0633 (2)	0.0680 (12)
H24D	0.6159	0.4739	0.0688	0.102*
H24C	0.5157	0.3040	0.0211	0.102*
H24B	0.6746	0.2552	0.0476	0.102*

	U11	U22	U33	U12	U13	U23
S1	0.0576 (5)	0.0388 (5)	0.0416 (4)	0.0113 (4)	0.0137 (3)	0.0032 (4)
N1	0.0428 (14)	0.0336 (15)	0.0403 (12)	0.0021 (14)	0.0101 (10)	0.0002 (14)
N2	0.088 (2)	0.057 (2)	0.0603 (18)	0.032 (2)	0.0280 (16)	0.015 (2)
O1	0.0559 (15)	0.0382 (15)	0.0538 (13)	0.0121 (11)	0.0188 (11)	−0.0001 (12)
O2	0.0834 (19)	0.0566 (19)	0.0504 (14)	0.0275 (16)	0.0252 (13)	0.0067 (14)
O3	0.103 (2)	0.080 (2)	0.0808 (19)	0.051 (2)	0.0368 (16)	0.034 (2)
C1	0.051 (2)	0.037 (2)	0.0476 (19)	0.0041 (15)	0.0099 (15)	−0.0022 (15)
C2	0.051 (2)	0.038 (2)	0.0480 (18)	0.0042 (16)	0.0122 (15)	−0.0086 (15)
C3	0.042 (2)	0.043 (2)	0.0524 (19)	0.0005 (15)	0.0056 (15)	−0.0141 (17)
C4	0.056 (2)	0.057 (3)	0.067 (2)	0.012 (2)	0.0123 (17)	−0.021 (2)
C5	0.056 (2)	0.050 (3)	0.089 (3)	0.021 (2)	0.005 (2)	−0.018 (2)
C6	0.052 (2)	0.041 (2)	0.087 (3)	0.0102 (18)	0.002 (2)	0.003 (2)
C7	0.048 (2)	0.046 (2)	0.069 (2)	0.0011 (19)	0.0105 (16)	0.001 (2)
C8	0.0388 (19)	0.035 (2)	0.060 (2)	0.0044 (15)	0.0093 (15)	−0.0044 (16)
C9	0.056 (2)	0.032 (2)	0.0478 (18)	0.0040 (17)	0.0091 (15)	−0.0048 (16)
C10	0.0428 (19)	0.0297 (18)	0.0475 (17)	−0.0001 (14)	0.0095 (14)	0.0002 (15)
C11	0.0422 (18)	0.0340 (19)	0.0343 (15)	−0.0012 (14)	0.0086 (13)	−0.0007 (13)
C12	0.049 (2)	0.037 (2)	0.0472 (18)	0.0065 (16)	0.0119 (15)	0.0031 (16)
C13	0.042 (2)	0.035 (2)	0.0489 (17)	0.0040 (14)	0.0060 (14)	0.0010 (15)
C14	0.060 (2)	0.046 (2)	0.055 (2)	0.0197 (19)	0.0148 (17)	0.0006 (19)
C15	0.057 (2)	0.040 (2)	0.057 (2)	0.0123 (17)	0.0098 (17)	0.0071 (17)
C16	0.072 (3)	0.052 (3)	0.052 (2)	0.008 (2)	0.0094 (18)	0.0144 (19)
C17	0.047 (2)	0.0349 (19)	0.055 (2)	0.0070 (16)	0.0174 (16)	−0.0003 (17)
C18	0.0425 (18)	0.0314 (19)	0.0407 (16)	0.0066 (13)	0.0112 (13)	0.0004 (13)
C19	0.049 (2)	0.042 (2)	0.058 (2)	0.0021 (17)	0.0161 (16)	0.0010 (18)
C20	0.072 (3)	0.050 (3)	0.075 (3)	0.008 (2)	0.036 (2)	0.020 (2)
C21	0.076 (3)	0.084 (4)	0.049 (2)	0.020 (3)	0.018 (2)	0.020 (2)
C22	0.066 (3)	0.082 (4)	0.0483 (19)	0.013 (3)	0.0006 (17)	−0.009 (2)
C23	0.0476 (19)	0.049 (2)	0.0528 (18)	−0.0024 (19)	0.0118 (15)	−0.008 (2)
C24	0.079 (3)	0.070 (3)	0.060 (2)	0.011 (2)	0.029 (2)	−0.002 (2)

S1—C11	1.725 (3)	C10—C17	1.425 (4)
S1—C12	1.752 (4)	C12—C13	1.363 (4)
N1—C11	1.372 (4)	C12—C15	1.467 (5)
N1—C13	1.377 (5)	C13—C14	1.493 (4)
N1—C18	1.456 (4)	C14—H14A	0.9600
N2—C17	1.144 (4)	C14—H14B	0.9600
O1—C8	1.368 (4)	C14—H14C	0.9600
O1—C1	1.396 (4)	C15—C16	1.496 (5)
O2—C9	1.233 (4)	C16—H16A	0.9600
O3—C15	1.213 (5)	C16—H16B	0.9600
C1—C2	1.361 (5)	C16—H16C	0.9600
C1—C9	1.465 (5)	C18—C23	1.369 (5)
C2—C3	1.451 (5)	C18—C19	1.375 (4)
C2—C24	1.494 (5)	C19—C20	1.384 (5)
C3—C8	1.390 (5)	C19—H19A	0.9300
C3—C4	1.396 (5)	C20—C21	1.363 (6)
C4—C5	1.358 (6)	C20—H20A	0.9300
C4—H4A	0.9300	C21—C22	1.370 (6)
C5—C6	1.394 (5)	C21—H21A	0.9300
C5—H5A	0.9300	C22—C23	1.393 (5)
C6—C7	1.378 (5)	C22—H22A	0.9300
C6—H6A	0.9300	C23—H23A	0.9300
C7—C8	1.370 (5)	C24—H24D	0.9600
C7—H7A	0.9300	C24—H24C	0.9600
C9—C10	1.444 (4)	C24—H24B	0.9600
C10—C11	1.409 (5)
C11—S1—C12	91.20 (16)	C12—C13—C14	128.5 (3)
C11—N1—C13	115.5 (3)	N1—C13—C14	119.3 (3)
C11—N1—C18	123.1 (3)	C13—C14—H14A	109.5
C13—N1—C18	121.3 (3)	C13—C14—H14B	109.5
C8—O1—C1	106.4 (2)	H14A—C14—H14B	109.5
C2—C1—O1	111.3 (3)	C13—C14—H14C	109.5
C2—C1—C9	128.1 (3)	H14A—C14—H14C	109.5
O1—C1—C9	120.6 (3)	H14B—C14—H14C	109.5
C1—C2—C3	105.6 (3)	O3—C15—C12	121.8 (3)
C1—C2—C24	130.1 (4)	O3—C15—C16	120.8 (4)
C3—C2—C24	124.3 (3)	C12—C15—C16	117.4 (3)
C8—C3—C4	118.7 (4)	C15—C16—H16A	109.5
C8—C3—C2	106.6 (3)	C15—C16—H16B	109.5
C4—C3—C2	134.7 (4)	H16A—C16—H16B	109.5
C5—C4—C3	118.6 (4)	C15—C16—H16C	109.5
C5—C4—H4A	120.7	H16A—C16—H16C	109.5
C3—C4—H4A	120.7	H16B—C16—H16C	109.5
C4—C5—C6	121.2 (4)	N2—C17—C10	178.4 (4)
C4—C5—H5A	119.4	C23—C18—C19	122.4 (3)
C6—C5—H5A	119.4	C23—C18—N1	118.6 (3)
C7—C6—C5	121.6 (4)	C19—C18—N1	119.0 (3)
C7—C6—H6A	119.2	C18—C19—C20	118.3 (4)
C5—C6—H6A	119.2	C18—C19—H19A	120.9
C8—C7—C6	116.2 (3)	C20—C19—H19A	120.9
C8—C7—H7A	121.9	C21—C20—C19	120.5 (4)
C6—C7—H7A	121.9	C21—C20—H20A	119.8
O1—C8—C7	126.3 (3)	C19—C20—H20A	119.8
O1—C8—C3	110.1 (3)	C20—C21—C22	120.5 (4)
C7—C8—C3	123.7 (3)	C20—C21—H21A	119.7
O2—C9—C10	119.8 (3)	C22—C21—H21A	119.7
O2—C9—C1	116.2 (3)	C21—C22—C23	120.3 (4)
C10—C9—C1	124.0 (3)	C21—C22—H22A	119.9
C11—C10—C17	122.1 (3)	C23—C22—H22A	119.9
C11—C10—C9	116.5 (3)	C18—C23—C22	118.1 (4)
C17—C10—C9	121.4 (3)	C18—C23—H23A	121.0
N1—C11—C10	127.6 (3)	C22—C23—H23A	121.0
N1—C11—S1	109.9 (2)	C2—C24—H24D	109.5
C10—C11—S1	122.6 (2)	C2—C24—H24C	109.5
C13—C12—C15	127.9 (3)	H24D—C24—H24C	109.5
C13—C12—S1	111.2 (3)	C2—C24—H24B	109.5
C15—C12—S1	120.9 (3)	H24D—C24—H24B	109.5
C12—C13—N1	112.3 (3)	H24C—C24—H24B	109.5
C8—O1—C1—C2	−0.7 (4)	C18—N1—C11—S1	−173.8 (2)
C8—O1—C1—C9	179.4 (3)	C17—C10—C11—N1	−0.2 (5)
O1—C1—C2—C3	0.9 (4)	C9—C10—C11—N1	−178.1 (3)
C9—C1—C2—C3	−179.2 (3)	C17—C10—C11—S1	179.8 (3)
O1—C1—C2—C24	−179.3 (4)	C9—C10—C11—S1	1.9 (4)
C9—C1—C2—C24	0.6 (7)	C12—S1—C11—N1	−1.1 (3)
C1—C2—C3—C8	−0.8 (4)	C12—S1—C11—C10	178.9 (3)
C24—C2—C3—C8	179.4 (4)	C11—S1—C12—C13	0.2 (3)
C1—C2—C3—C4	179.0 (4)	C11—S1—C12—C15	178.9 (3)
C24—C2—C3—C4	−0.8 (7)	C15—C12—C13—N1	−177.8 (3)
C8—C3—C4—C5	0.3 (6)	S1—C12—C13—N1	0.7 (4)
C2—C3—C4—C5	−179.4 (4)	C15—C12—C13—C14	1.6 (7)
C3—C4—C5—C6	−0.7 (6)	S1—C12—C13—C14	−179.9 (3)
C4—C5—C6—C7	0.0 (6)	C11—N1—C13—C12	−1.6 (4)
C5—C6—C7—C8	1.1 (6)	C18—N1—C13—C12	174.0 (3)
C1—O1—C8—C7	179.8 (3)	C11—N1—C13—C14	178.9 (3)
C1—O1—C8—C3	0.1 (4)	C18—N1—C13—C14	−5.4 (5)
C6—C7—C8—O1	178.8 (3)	C13—C12—C15—O3	−7.9 (7)
C6—C7—C8—C3	−1.6 (6)	S1—C12—C15—O3	173.7 (3)
C4—C3—C8—O1	−179.4 (3)	C13—C12—C15—C16	170.0 (4)
C2—C3—C8—O1	0.4 (4)	S1—C12—C15—C16	−8.4 (5)
C4—C3—C8—C7	0.9 (5)	C11—N1—C18—C23	82.6 (4)
C2—C3—C8—C7	−179.3 (3)	C13—N1—C18—C23	−92.7 (4)
C2—C1—C9—O2	8.2 (6)	C11—N1—C18—C19	−97.8 (4)
O1—C1—C9—O2	−172.0 (3)	C13—N1—C18—C19	86.9 (4)
C2—C1—C9—C10	−171.7 (4)	C23—C18—C19—C20	−1.0 (5)
O1—C1—C9—C10	8.2 (5)	N1—C18—C19—C20	179.5 (3)
O2—C9—C10—C11	−1.3 (5)	C18—C19—C20—C21	−0.8 (6)
C1—C9—C10—C11	178.5 (3)	C19—C20—C21—C22	1.7 (7)
O2—C9—C10—C17	−179.3 (3)	C20—C21—C22—C23	−0.8 (7)
C1—C9—C10—C17	0.6 (5)	C19—C18—C23—C22	1.9 (6)
C13—N1—C11—C10	−178.2 (3)	N1—C18—C23—C22	−178.6 (4)
C18—N1—C11—C10	6.2 (5)	C21—C22—C23—C18	−1.0 (6)
C13—N1—C11—S1	1.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O3	0.96	2.30	2.999 (5)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O3	0.96	2.30	2.999 (5)	129