2-Phenyl-4-(3,4,5-trimethoxy-benzyl-idene)-1,3-oxazol-5(4H)-one.

The title compound, C(19)H(17)NO(5), was synthesized as part of a continuing project involving the structures of oxazolone derivatives. The mol-ecule adopts a Z configuration about the central olefinic bond. The 2-phenyl ring is slightly twisted out of the plane of the oxazolone ring system by 11.2 (2)°. The crystal structure is stabilized by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For background literature, see: Aaglawe et al. (2003 ▶); Grassi et al. (2004 ▶); Khan et al. (2006 ▶); Song et al. (2001 ▶). For related structures, see: Sun et al. (2007 ▶); Imhof & Garms (2005 ▶); Song et al. (2004 ▶); Vasuki et al. (2001 ▶).

Experimental

Crystal data

C19H17NO5

M = 339.34

Triclinic,

a = 7.3897 (5) Å

b = 8.1532 (6) Å

c = 14.0023 (9) Å

α = 86.917 (5)°

β = 83.306 (4)°

γ = 82.471 (5)°

V = 830.02 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 273 (2) K

0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.985, T max = 0.990

4665 measured reflections

2904 independent reflections

2056 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.121

S = 1.04

2904 reflections

229 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005746/pk2085sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005746/pk2085Isup2.hkl

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

C19H17NO5	Z = 2
Mr = 339.34	F000 = 356
Triclinic, P1	Dx = 1.358 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.3897 (5) Å	Cell parameters from 1358 reflections
b = 8.1532 (6) Å	θ = 2.9–24.7º
c = 14.0023 (9) Å	µ = 0.10 mm−1
α = 86.917 (5)º	T = 273 (2) K
β = 83.306 (4)º	Block, yellow
γ = 82.471 (5)º	0.15 × 0.12 × 0.10 mm
V = 830.02 (10) Å3

Bruker SMART CCD area detector diffractometer	2904 independent reflections
Radiation source: fine-focus sealed tube	2056 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
T = 273(2) K	θmax = 25.1º
φ and ω scans	θmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.985, Tmax = 0.990	k = −9→8
4665 measured reflections	l = −16→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.121	w = 1/[σ2(Fo2) + (0.0602P)2 + 0.0668P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2904 reflections	Δρmax = 0.12 e Å−3
229 parameters	Δρmin = −0.15 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 > 2σ(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
O1	0.5421 (2)	0.11697 (18)	−0.16116 (10)	0.0843 (5)
O2	0.47613 (18)	0.36419 (17)	−0.23924 (9)	0.0666 (4)
O3	−0.0038 (2)	0.77451 (16)	0.17976 (10)	0.0760 (4)
O4	−0.0466 (2)	0.58784 (18)	0.33970 (10)	0.0759 (4)
O5	0.09472 (19)	0.26856 (16)	0.34793 (9)	0.0685 (4)
N1	0.3293 (2)	0.51906 (19)	−0.11774 (10)	0.0559 (4)
C1	0.4742 (3)	0.2583 (3)	−0.15782 (14)	0.0626 (5)
C2	0.3888 (2)	0.5149 (2)	−0.20767 (13)	0.0560 (5)
C3	0.3759 (2)	0.3591 (2)	−0.07986 (13)	0.0546 (4)
C4	0.3748 (2)	0.6523 (2)	−0.27805 (12)	0.0567 (5)
C5	0.3176 (3)	0.8105 (3)	−0.24711 (14)	0.0656 (5)
H5	0.2910	0.8276	−0.1816	0.079*
C6	0.2996 (3)	0.9427 (3)	−0.31155 (15)	0.0720 (6)
H6	0.2600	1.0486	−0.2898	0.086*
C7	0.3402 (3)	0.9181 (3)	−0.40840 (15)	0.0764 (6)
H7	0.3282	1.0074	−0.4524	0.092*
C8	0.3981 (3)	0.7630 (3)	−0.43997 (15)	0.0836 (7)
H8	0.4258	0.7471	−0.5056	0.100*
C9	0.4161 (3)	0.6292 (3)	−0.37596 (14)	0.0742 (6)
H9	0.4558	0.5237	−0.3983	0.089*
C10	0.3399 (2)	0.2976 (2)	0.01042 (13)	0.0566 (5)
H10	0.3867	0.1873	0.0207	0.068*
C11	0.2390 (2)	0.3772 (2)	0.09430 (12)	0.0509 (4)
C12	0.1654 (2)	0.5438 (2)	0.09198 (13)	0.0551 (4)
H12	0.1786	0.6078	0.0352	0.066*
C13	0.0733 (2)	0.6129 (2)	0.17411 (13)	0.0560 (4)
C14	0.0515 (2)	0.5183 (2)	0.25978 (12)	0.0561 (5)
C15	0.1226 (2)	0.3522 (2)	0.26160 (12)	0.0535 (4)
C16	0.2174 (2)	0.2820 (2)	0.17932 (12)	0.0541 (4)
H16	0.2666	0.1710	0.1810	0.065*
C17	0.0240 (3)	0.8792 (2)	0.09656 (15)	0.0776 (6)
H17A	0.1533	0.8797	0.0785	0.116*
H17B	−0.0321	0.9897	0.1101	0.116*
H17C	−0.0303	0.8391	0.0448	0.116*
C18	0.0640 (4)	0.6488 (3)	0.40255 (16)	0.1007 (8)
H18A	0.1511	0.5600	0.4234	0.151*
H18B	−0.0125	0.6940	0.4575	0.151*
H18C	0.1284	0.7337	0.3694	0.151*
C19	0.1573 (3)	0.0968 (3)	0.35144 (15)	0.0724 (6)
H19A	0.1064	0.0437	0.3030	0.109*
H19B	0.1190	0.0500	0.4137	0.109*
H19C	0.2889	0.0802	0.3399	0.109*

	U11	U22	U33	U12	U13	U23
O1	0.1024 (12)	0.0654 (10)	0.0810 (10)	0.0056 (8)	−0.0041 (8)	−0.0184 (8)
O2	0.0715 (8)	0.0709 (9)	0.0554 (7)	−0.0040 (7)	0.0000 (6)	−0.0128 (7)
O3	0.0942 (11)	0.0559 (8)	0.0699 (9)	0.0064 (7)	0.0051 (7)	0.0006 (7)
O4	0.0790 (9)	0.0789 (9)	0.0652 (8)	−0.0073 (7)	0.0123 (7)	−0.0120 (7)
O5	0.0813 (9)	0.0644 (8)	0.0575 (8)	−0.0123 (7)	0.0021 (6)	0.0062 (6)
N1	0.0542 (9)	0.0615 (10)	0.0526 (9)	−0.0109 (7)	−0.0033 (7)	−0.0048 (7)
C1	0.0636 (12)	0.0642 (13)	0.0608 (11)	−0.0072 (10)	−0.0074 (9)	−0.0108 (10)
C2	0.0492 (10)	0.0639 (12)	0.0564 (11)	−0.0098 (8)	−0.0043 (8)	−0.0124 (9)
C3	0.0531 (10)	0.0557 (11)	0.0561 (10)	−0.0084 (8)	−0.0068 (8)	−0.0067 (9)
C4	0.0490 (10)	0.0685 (12)	0.0537 (10)	−0.0114 (9)	−0.0047 (8)	−0.0052 (9)
C5	0.0624 (12)	0.0762 (14)	0.0563 (11)	−0.0055 (10)	−0.0022 (9)	−0.0031 (10)
C6	0.0673 (13)	0.0734 (14)	0.0740 (14)	−0.0078 (10)	−0.0058 (10)	0.0020 (11)
C7	0.0715 (13)	0.0897 (16)	0.0693 (13)	−0.0199 (12)	−0.0095 (11)	0.0132 (12)
C8	0.0985 (17)	0.0996 (18)	0.0541 (12)	−0.0228 (14)	−0.0034 (11)	−0.0001 (12)
C9	0.0891 (15)	0.0769 (14)	0.0570 (12)	−0.0157 (11)	−0.0004 (10)	−0.0088 (10)
C10	0.0578 (11)	0.0521 (10)	0.0613 (11)	−0.0089 (8)	−0.0086 (9)	−0.0049 (8)
C11	0.0502 (10)	0.0510 (10)	0.0530 (10)	−0.0107 (8)	−0.0063 (8)	−0.0042 (8)
C12	0.0585 (11)	0.0547 (11)	0.0520 (10)	−0.0098 (8)	−0.0044 (8)	0.0010 (8)
C13	0.0556 (10)	0.0509 (10)	0.0606 (11)	−0.0049 (8)	−0.0042 (9)	−0.0030 (9)
C14	0.0527 (10)	0.0600 (11)	0.0552 (10)	−0.0097 (8)	0.0014 (8)	−0.0076 (9)
C15	0.0521 (10)	0.0579 (11)	0.0519 (10)	−0.0137 (8)	−0.0054 (8)	0.0020 (8)
C16	0.0542 (10)	0.0495 (10)	0.0600 (11)	−0.0100 (8)	−0.0086 (8)	−0.0010 (8)
C17	0.0939 (16)	0.0551 (12)	0.0790 (14)	0.0018 (11)	−0.0067 (12)	0.0070 (10)
C18	0.146 (2)	0.0862 (17)	0.0716 (14)	−0.0273 (16)	0.0020 (15)	−0.0237 (12)
C19	0.0762 (13)	0.0681 (14)	0.0708 (13)	−0.0087 (11)	−0.0078 (11)	0.0161 (10)

O1—C1	1.196 (2)	C8—C9	1.377 (3)
O2—C2	1.381 (2)	C8—H8	0.9300
O2—C1	1.393 (2)	C9—H9	0.9300
O3—C13	1.368 (2)	C10—C11	1.452 (2)
O3—C17	1.418 (2)	C10—H10	0.9300
O4—C14	1.368 (2)	C11—C16	1.391 (2)
O4—C18	1.418 (3)	C11—C12	1.396 (2)
O5—C15	1.363 (2)	C12—C13	1.374 (2)
O5—C19	1.417 (2)	C12—H12	0.9300
N1—C2	1.285 (2)	C13—C14	1.396 (3)
N1—C3	1.397 (2)	C14—C15	1.387 (3)
C1—C3	1.466 (3)	C15—C16	1.387 (2)
C2—C4	1.453 (3)	C16—H16	0.9300
C3—C10	1.345 (3)	C17—H17A	0.9600
C4—C5	1.380 (3)	C17—H17B	0.9600
C4—C9	1.387 (3)	C17—H17C	0.9600
C5—C6	1.371 (3)	C18—H18A	0.9600
C5—H5	0.9300	C18—H18B	0.9600
C6—C7	1.374 (3)	C18—H18C	0.9600
C6—H6	0.9300	C19—H19A	0.9600
C7—C8	1.361 (3)	C19—H19B	0.9600
C7—H7	0.9300	C19—H19C	0.9600
C2—O2—C1	105.35 (14)	C16—C11—C10	117.84 (16)
C13—O3—C17	117.23 (15)	C12—C11—C10	122.32 (16)
C14—O4—C18	113.61 (16)	C13—C12—C11	119.65 (16)
C15—O5—C19	117.33 (15)	C13—C12—H12	120.2
C2—N1—C3	105.67 (15)	C11—C12—H12	120.2
O1—C1—O2	121.82 (18)	O3—C13—C12	124.40 (16)
O1—C1—C3	133.22 (19)	O3—C13—C14	114.73 (16)
O2—C1—C3	104.96 (17)	C12—C13—C14	120.87 (17)
N1—C2—O2	115.89 (16)	O4—C14—C15	120.64 (16)
N1—C2—C4	126.61 (17)	O4—C14—C13	119.91 (17)
O2—C2—C4	117.50 (15)	C15—C14—C13	119.39 (16)
C10—C3—N1	129.17 (16)	O5—C15—C16	124.20 (16)
C10—C3—C1	122.71 (18)	O5—C15—C14	115.69 (16)
N1—C3—C1	108.10 (15)	C16—C15—C14	120.10 (16)
C5—C4—C9	118.72 (18)	C15—C16—C11	120.14 (16)
C5—C4—C2	119.35 (16)	C15—C16—H16	119.9
C9—C4—C2	121.92 (18)	C11—C16—H16	119.9
C6—C5—C4	120.99 (18)	O3—C17—H17A	109.5
C6—C5—H5	119.5	O3—C17—H17B	109.5
C4—C5—H5	119.5	H17A—C17—H17B	109.5
C5—C6—C7	119.7 (2)	O3—C17—H17C	109.5
C5—C6—H6	120.1	H17A—C17—H17C	109.5
C7—C6—H6	120.1	H17B—C17—H17C	109.5
C8—C7—C6	120.0 (2)	O4—C18—H18A	109.5
C8—C7—H7	120.0	O4—C18—H18B	109.5
C6—C7—H7	120.0	H18A—C18—H18B	109.5
C7—C8—C9	120.8 (2)	O4—C18—H18C	109.5
C7—C8—H8	119.6	H18A—C18—H18C	109.5
C9—C8—H8	119.6	H18B—C18—H18C	109.5
C8—C9—C4	119.8 (2)	O5—C19—H19A	109.5
C8—C9—H9	120.1	O5—C19—H19B	109.5
C4—C9—H9	120.1	H19A—C19—H19B	109.5
C3—C10—C11	129.81 (17)	O5—C19—H19C	109.5
C3—C10—H10	115.1	H19A—C19—H19C	109.5
C11—C10—H10	115.1	H19B—C19—H19C	109.5
C16—C11—C12	119.84 (16)
C2—O2—C1—O1	−179.16 (18)	C1—C3—C10—C11	−177.22 (17)
C2—O2—C1—C3	1.44 (18)	C3—C10—C11—C16	178.06 (17)
C3—N1—C2—O2	−0.07 (19)	C3—C10—C11—C12	−2.3 (3)
C3—N1—C2—C4	−179.39 (16)	C16—C11—C12—C13	0.5 (3)
C1—O2—C2—N1	−0.9 (2)	C10—C11—C12—C13	−179.12 (16)
C1—O2—C2—C4	178.45 (15)	C17—O3—C13—C12	−4.2 (3)
C2—N1—C3—C10	−177.93 (18)	C17—O3—C13—C14	176.14 (17)
C2—N1—C3—C1	1.01 (18)	C11—C12—C13—O3	179.96 (16)
O1—C1—C3—C10	−1.8 (3)	C11—C12—C13—C14	−0.4 (3)
O2—C1—C3—C10	177.47 (16)	C18—O4—C14—C15	87.7 (2)
O1—C1—C3—N1	179.2 (2)	C18—O4—C14—C13	−95.3 (2)
O2—C1—C3—N1	−1.55 (19)	O3—C13—C14—O4	2.2 (2)
N1—C2—C4—C5	10.3 (3)	C12—C13—C14—O4	−177.52 (16)
O2—C2—C4—C5	−168.97 (16)	O3—C13—C14—C15	179.23 (15)
N1—C2—C4—C9	−169.19 (18)	C12—C13—C14—C15	−0.5 (3)
O2—C2—C4—C9	11.5 (3)	C19—O5—C15—C16	−4.0 (2)
C9—C4—C5—C6	0.8 (3)	C19—O5—C15—C14	176.91 (16)
C2—C4—C5—C6	−178.80 (17)	O4—C14—C15—O5	−2.7 (2)
C4—C5—C6—C7	−0.5 (3)	C13—C14—C15—O5	−179.76 (15)
C5—C6—C7—C8	0.0 (3)	O4—C14—C15—C16	178.17 (15)
C6—C7—C8—C9	0.2 (3)	C13—C14—C15—C16	1.1 (3)
C7—C8—C9—C4	0.0 (3)	O5—C15—C16—C11	180.00 (15)
C5—C4—C9—C8	−0.5 (3)	C14—C15—C16—C11	−1.0 (3)
C2—C4—C9—C8	179.02 (19)	C12—C11—C16—C15	0.1 (2)
N1—C3—C10—C11	1.6 (3)	C10—C11—C16—C15	179.81 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1i	0.93	2.59	3.503 (2)	168
C6—H6···O3ii	0.93	2.62	3.420 (2)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O1i	0.93	2.59	3.503 (2)	168
C6—H6⋯O3ii	0.93	2.62	3.420 (2)	144

Symmetry codes: (i) ; (ii) .