(Z)-2-(5-Acetyl-4-methyl-3-phenyl-2,3-dihydro-1,3-thia­zol-2-yl­idene)-3-(3-methyl-1-benzofuran-2-yl)-3-oxo­propane­nitrile

Fun, H.-K.; Quah, C.K.; Abdel-Aziz, H.A.; Ghabbour, H.A.

doi:10.1107/S1600536812035039

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2727

doi:10.1107/S1600536812035039

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(Z)-2-(5-Acetyl-4-methyl-3-phenyl-2,3-dihydro-1,3-thiazol-2-ylidene)-3-(3-methyl-1-benzofuran-2-yl)-3-oxopropanenitrile

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § Hatem A. Abdel-Aziz ^b and Hazem A. Ghabbour ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia
^*Correspondence e-mail: hkfun@usm.my

(Received 24 July 2012; accepted 8 August 2012; online 15 August 2012)

In the title compound, C₂₄H₁₈N₂O₃S, 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 thiazole rings, respectively. The dihedral angle between the benzene and thiazole rings is 84.51 (19)°. The molecular structure features an intramolecular C—H⋯O hydrogen bond, which closes an S(6) ring. There are no intermolecular 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_r = 414.46
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.119
S = 1.01
2831 reflections
275 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.32 e Å⁻³
Absolute structure: Flack (1983 ), 831 Friedel pairs
Flack parameter: 0.03 (3)

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

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812035039/hb6913sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812035039/hb6913Isup3.cml

checkCIF report

Comment top

In continuation of our interest in the structures and properties of benzofuran derivatives (Abdel-Aziz et al., 2009; Abdel-Wahab et al., 2009), we publish here the crystal structure of the title compound.

In the title molecule, Fig. 1, the benzofuran-2-yl ring system (O1/C1-C8, r.m.s. deviation = 0.010 Å) forms dihedral angles of 83.13 (17) and 8.92 (14)° with the benzene (C18-C23) and thiazol (S1/N1/C11-C13) rings, respectively. The dihedral angle between benzene and thiazol rings is 84.51 (19)°. Bond lengths and angles are comparable to related structures (Fun et al., 2012; Abdel-Aziz et al., 2012). The crystal structure is features an intramolecular C14–H14A···O3 hydrogen bond, forming an S(6) ring motif (Bernstein et al., 1995).

There is no significant intermolecular hydrogen bond observed in this compound.

Related literature top

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 top

To a solution of 2-cyano-2-(3-methylbenzofuran-2-carbonyl)thioacetanilide (Dawood et al., 2005), (0.33 g, 1 mmol) in ethanol (25 mL) and 3-chloropentane-2,4-dione (0.135 g, 1 mmol), triethylamine (0.2 mL) was added. The mixture was refluxed for 2 h, and then allowed to cool. The formed solid was filtered off, washed with ethanol, and recrystallized from EtOH/DMF solution to afford yellow needles of the title compound.

Computing details top

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

Figures top

Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids for non-H atoms. Intramolecular hydrogen bond is shown as dashed line.

(Z)-2-(5-Acetyl-4-methyl-3-phenyl-2,3-dihydro-1,3-thiazol-2-ylidene)- 3-(3-methyl-1-benzofuran-2-yl)-3-oxopropanenitrile top

Crystal data top

C₂₄H₁₈N₂O₃S	F(000) = 432
M_r = 414.46	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0714P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
2831 reflections	Δρ_max = 0.25 e Å⁻³
275 parameters	Δρ_min = −0.32 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 831 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (3)

Crystal data top

C₂₄H₁₈N₂O₃S	V = 994.92 (7) Å³
M_r = 414.46	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 9.7836 (4) Å	µ = 1.69 mm⁻¹
b = 6.3682 (3) Å	T = 296 K
c = 16.2330 (6) Å	0.92 × 0.09 × 0.06 mm
β = 100.351 (3)°

Data collection top

Bruker SMART APEXII CCD diffractometer	2831 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2310 reflections with I > 2σ(I)
T_min = 0.306, T_max = 0.906	R_int = 0.041
7151 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.119	Δρ_max = 0.25 e Å⁻³
S = 1.01	Δρ_min = −0.32 e Å⁻³
2831 reflections	Absolute structure: Flack (1983), 831 Friedel pairs
275 parameters	Absolute structure parameter: 0.03 (3)
1 restraint

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₂₄H₁₈N₂O₃S
M_r	414.46
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	9.7836 (4), 6.3682 (3), 16.2330 (6)
β (°)	100.351 (3)
V (Å³)	994.92 (7)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	1.69
Crystal size (mm)	0.92 × 0.09 × 0.06

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.306, 0.906
No. of measured, independent and observed [I > 2σ(I)] reflections	7151, 2831, 2310
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.119, 1.01
No. of reflections	2831
No. of parameters	275
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.32
Absolute structure	Flack (1983), 831 Friedel pairs
Absolute structure parameter	0.03 (3)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

The authors thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University. HKF and CKQ thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160).

References

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