(Z)-4-(4-Methoxy­benzyl­idene)-2-methyl­sulfan­yl-3-pheneth­yl-1H-imidazol-5(4H)-one

The title mol­ecule, C₂₀H₂₀N₂O₂S, exits in the Z form and the five-membered imidazole ring and the benzene ring of the 4-methoxy­benzyl­idene moiety are almost coplanar. Short intra­molecular contacts [C...S = 3.138 (4) Å and C...N = 3.060 (4) Å] indicate the presence of weak C—H...S and C—H...N intra­molecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• R factor = 0.082
• wR factor = 0.173
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

(Z)-4-(4-Methoxybenzylidene)-2-methylsulfanyl-3-phenethyl-1H-imidazol-5(4H)-one

Crystal data

C20H20N2O2S	Z = 2
Mr = 352.44	F(000) = 372
Triclinic, P1	Dx = 1.290 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7833 (10) Å	Cell parameters from 1514 reflections
b = 9.9027 (10) Å	θ = 2.6–24.3°
c = 10.2853 (11) Å	µ = 0.19 mm^−1
α = 101.957 (2)°	T = 298 K
β = 104.951 (2)°	Block, colorless
γ = 101.511 (2)°	0.27 × 0.21 × 0.13 mm
V = 907.46 (16) Å^3

Data collection

Bruker APEX area-detector diffractometer	3264 independent reflections
Radiation source: fine-focus sealed tube	2723 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 25.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −11→11
Tmin = 0.950, Tmax = 0.975	k = −11→11
6756 measured reflections	l = −11→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.173	H-atom parameters constrained
S = 1.29	w = 1/[σ^2(Fo^2) + (0.059P)^2 + 0.3033P] where P = (Fo^2 + 2Fc^2)/3
3264 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.50209 (11)	0.61314 (10)	0.84456 (9)	0.0621 (3)
O1	0.1406 (3)	0.3660 (3)	0.3744 (3)	0.0749 (8)
O2	0.6707 (3)	1.0700 (3)	0.1980 (3)	0.0673 (7)
N1	0.2948 (3)	0.4583 (3)	0.6018 (3)	0.0528 (7)
N2	0.4485 (3)	0.6532 (3)	0.5857 (3)	0.0479 (7)
C1	−0.0364 (4)	0.1606 (4)	0.7171 (4)	0.0792 (12)
H1	−0.0477	0.1267	0.6226	0.095*
C2	−0.0959 (5)	0.0687 (5)	0.7855 (6)	0.0915 (14)
H2	−0.1461	−0.0260	0.7372	0.110*
C3	−0.0804 (5)	0.1182 (5)	0.9239 (5)	0.0823 (13)
H3	−0.1222	0.0577	0.9696	0.099*
C4	−0.0044 (4)	0.2552 (5)	0.9951 (4)	0.0790 (13)
H4	0.0077	0.2882	1.0899	0.095*
C5	0.0550 (4)	0.3453 (4)	0.9266 (4)	0.0676 (10)
H5	0.1074	0.4391	0.9765	0.081*
C6	0.0389 (4)	0.3007 (4)	0.7865 (4)	0.0540 (9)
C7	0.1041 (4)	0.4011 (4)	0.7127 (4)	0.0684 (11)
H7A	0.0277	0.4025	0.6317	0.082*
H7B	0.1414	0.4973	0.7752	0.082*
C8	0.2265 (4)	0.3574 (3)	0.6663 (4)	0.0579 (9)
H8A	0.3004	0.3508	0.7465	0.070*
H8B	0.1879	0.2633	0.5998	0.070*
C9	0.4144 (3)	0.5774 (3)	0.6674 (3)	0.0477 (8)
C10	0.3452 (3)	0.5849 (3)	0.4542 (3)	0.0473 (8)
C11	0.2441 (4)	0.4554 (4)	0.4626 (4)	0.0534 (8)
C12	0.3336 (3)	0.6248 (3)	0.3353 (3)	0.0494 (8)
H12	0.2557	0.5666	0.2583	0.059*
C13	0.4242 (3)	0.7447 (3)	0.3086 (3)	0.0447 (7)
C14	0.3934 (4)	0.7582 (4)	0.1727 (3)	0.0554 (9)
H14	0.3146	0.6913	0.1024	0.067*
C15	0.4760 (4)	0.8672 (4)	0.1396 (3)	0.0579 (9)
H15	0.4524	0.8740	0.0480	0.070*
C16	0.5937 (4)	0.9668 (3)	0.2417 (3)	0.0494 (8)
C17	0.6258 (4)	0.9579 (4)	0.3784 (3)	0.0535 (9)
H17	0.7039	1.0258	0.4484	0.064*
C18	0.5411 (4)	0.8474 (3)	0.4102 (3)	0.0519 (8)
H18	0.5633	0.8422	0.5022	0.062*
C19	0.6400 (4)	0.7728 (4)	0.8683 (4)	0.0674 (10)
H19A	0.6995	0.7525	0.8096	0.101*
H19B	0.7006	0.8066	0.9644	0.101*
H19C	0.5939	0.8449	0.8438	0.101*
C20	0.8012 (4)	1.1660 (4)	0.2945 (4)	0.0723 (11)
H20A	0.7798	1.2163	0.3740	0.108*
H20B	0.8422	1.2335	0.2507	0.108*
H20C	0.8704	1.1136	0.3244	0.108*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0781 (7)	0.0593 (6)	0.0515 (6)	0.0090 (5)	0.0247 (5)	0.0243 (4)
O1	0.0677 (17)	0.0716 (17)	0.0702 (17)	−0.0108 (14)	0.0164 (14)	0.0218 (14)
O2	0.0774 (17)	0.0626 (15)	0.0648 (16)	0.0021 (13)	0.0276 (14)	0.0331 (13)
N1	0.0556 (17)	0.0503 (16)	0.0577 (18)	0.0050 (13)	0.0273 (14)	0.0223 (13)
N2	0.0518 (16)	0.0481 (15)	0.0504 (16)	0.0093 (13)	0.0228 (13)	0.0228 (13)
C1	0.081 (3)	0.079 (3)	0.068 (3)	−0.006 (2)	0.024 (2)	0.023 (2)
C2	0.091 (3)	0.066 (3)	0.112 (4)	−0.009 (2)	0.040 (3)	0.031 (3)
C3	0.069 (3)	0.096 (3)	0.107 (4)	0.018 (2)	0.042 (3)	0.068 (3)
C4	0.064 (3)	0.110 (4)	0.075 (3)	0.015 (3)	0.034 (2)	0.044 (3)
C5	0.058 (2)	0.069 (2)	0.076 (3)	0.0069 (19)	0.029 (2)	0.020 (2)
C6	0.0455 (19)	0.055 (2)	0.073 (2)	0.0129 (16)	0.0264 (17)	0.0321 (18)
C7	0.070 (2)	0.068 (2)	0.094 (3)	0.024 (2)	0.046 (2)	0.048 (2)
C8	0.062 (2)	0.051 (2)	0.073 (2)	0.0115 (17)	0.0341 (19)	0.0307 (18)
C9	0.0507 (19)	0.0473 (18)	0.0535 (19)	0.0140 (15)	0.0259 (16)	0.0183 (15)
C10	0.0474 (19)	0.0493 (18)	0.053 (2)	0.0129 (15)	0.0225 (16)	0.0216 (16)
C11	0.050 (2)	0.052 (2)	0.059 (2)	0.0072 (17)	0.0215 (17)	0.0181 (17)
C12	0.0439 (18)	0.0511 (19)	0.053 (2)	0.0077 (15)	0.0171 (15)	0.0159 (16)
C13	0.0442 (18)	0.0466 (18)	0.0472 (18)	0.0126 (15)	0.0178 (15)	0.0160 (15)
C14	0.057 (2)	0.056 (2)	0.0452 (19)	0.0058 (16)	0.0068 (16)	0.0162 (16)
C15	0.074 (2)	0.059 (2)	0.0444 (19)	0.0130 (19)	0.0185 (18)	0.0252 (17)
C16	0.060 (2)	0.0460 (18)	0.053 (2)	0.0180 (16)	0.0258 (17)	0.0220 (16)
C17	0.056 (2)	0.0519 (19)	0.0479 (19)	0.0044 (16)	0.0154 (16)	0.0144 (16)
C18	0.060 (2)	0.058 (2)	0.0459 (19)	0.0144 (17)	0.0246 (17)	0.0235 (16)
C19	0.062 (2)	0.068 (2)	0.068 (2)	0.0059 (19)	0.0171 (19)	0.0229 (19)
C20	0.074 (3)	0.062 (2)	0.086 (3)	0.004 (2)	0.036 (2)	0.032 (2)

Geometric parameters (Å, º)

S1—C9	1.728 (3)	C7—H7B	0.9700
S1—C19	1.788 (3)	C8—H8A	0.9700
O1—C11	1.211 (4)	C8—H8B	0.9700
O2—C16	1.368 (4)	C10—C12	1.346 (4)
O2—C20	1.410 (4)	C10—C11	1.488 (4)
N1—C11	1.381 (4)	C12—C13	1.453 (4)
N1—C9	1.388 (4)	C12—H12	0.9300
N1—C8	1.457 (4)	C13—C18	1.383 (4)
N2—C9	1.299 (4)	C13—C14	1.392 (4)
N2—C10	1.397 (4)	C14—C15	1.372 (4)
C1—C6	1.373 (5)	C14—H14	0.9300
C1—C2	1.388 (5)	C15—C16	1.376 (5)
C1—H1	0.9300	C15—H15	0.9300
C2—C3	1.363 (6)	C16—C17	1.384 (4)
C2—H2	0.9300	C17—C18	1.385 (4)
C3—C4	1.354 (6)	C17—H17	0.9300
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.377 (5)	C19—H19A	0.9600
C4—H4	0.9300	C19—H19B	0.9600
C5—C6	1.374 (5)	C19—H19C	0.9600
C5—H5	0.9300	C20—H20A	0.9600
C6—C7	1.510 (4)	C20—H20B	0.9600
C7—C8	1.505 (5)	C20—H20C	0.9600
C7—H7A	0.9700
C9—S1—C19	99.20 (16)	C12—C10—N2	127.6 (3)
C16—O2—C20	118.4 (3)	C12—C10—C11	123.1 (3)
C11—N1—C9	107.8 (3)	N2—C10—C11	109.3 (3)
C11—N1—C8	124.7 (3)	O1—C11—N1	125.6 (3)
C9—N1—C8	127.4 (3)	O1—C11—C10	131.3 (3)
C9—N2—C10	105.3 (3)	N1—C11—C10	103.0 (3)
C6—C1—C2	121.2 (4)	C10—C12—C13	129.9 (3)
C6—C1—H1	119.4	C10—C12—H12	115.0
C2—C1—H1	119.4	C13—C12—H12	115.0
C3—C2—C1	119.6 (4)	C18—C13—C14	117.2 (3)
C3—C2—H2	120.2	C18—C13—C12	124.1 (3)
C1—C2—H2	120.2	C14—C13—C12	118.7 (3)
C4—C3—C2	120.3 (4)	C15—C14—C13	121.8 (3)
C4—C3—H3	119.9	C15—C14—H14	119.1
C2—C3—H3	119.9	C13—C14—H14	119.1
C3—C4—C5	119.7 (4)	C14—C15—C16	120.1 (3)
C3—C4—H4	120.1	C14—C15—H15	119.9
C5—C4—H4	120.1	C16—C15—H15	119.9
C6—C5—C4	121.8 (4)	O2—C16—C15	115.8 (3)
C6—C5—H5	119.1	O2—C16—C17	124.7 (3)
C4—C5—H5	119.1	C15—C16—C17	119.5 (3)
C1—C6—C5	117.3 (3)	C16—C17—C18	119.6 (3)
C1—C6—C7	121.5 (4)	C16—C17—H17	120.2
C5—C6—C7	121.2 (3)	C18—C17—H17	120.2
C8—C7—C6	112.1 (3)	C13—C18—C17	121.7 (3)
C8—C7—H7A	109.2	C13—C18—H18	119.2
C6—C7—H7A	109.2	C17—C18—H18	119.2
C8—C7—H7B	109.2	S1—C19—H19A	109.5
C6—C7—H7B	109.2	S1—C19—H19B	109.5
H7A—C7—H7B	107.9	H19A—C19—H19B	109.5
N1—C8—C7	112.2 (3)	S1—C19—H19C	109.5
N1—C8—H8A	109.2	H19A—C19—H19C	109.5
C7—C8—H8A	109.2	H19B—C19—H19C	109.5
N1—C8—H8B	109.2	O2—C20—H20A	109.5
C7—C8—H8B	109.2	O2—C20—H20B	109.5
H8A—C8—H8B	107.9	H20A—C20—H20B	109.5
N2—C9—N1	114.6 (3)	O2—C20—H20C	109.5
N2—C9—S1	126.1 (3)	H20A—C20—H20C	109.5
N1—C9—S1	119.3 (2)	H20B—C20—H20C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···S1	0.97	2.74	3.138 (4)	105
C18—H18···N2	0.93	2.41	3.060 (4)	127