(E)-Methyl 2-[(4-bromo-2-formyl-phen-oxy)meth-yl]-3-phenyl-acrylate.

The C=C double bond in the title compound, C(18)H(15)BrO(4), adopts an E configuration. The two rings are almost orthogonal to each other, making a dihedral angle of 82.8 (1)°. An intra-molecular C-H⋯O hydrogen bond occurs. The crystal structure is stabilized by inter-molecular C-H⋯O hydrogen bonds.

Related literature

For background to the synthesis, see: Bakthadoss et al. (2009 ▶). For related phenyl acrylate compounds, see: Wang & Kong (2006 ▶); Wang et al. (2011 ▶). For the biological properties of cinnamate, see: Sharma (2011 ▶).

Experimental

Crystal data

C18H15BrO4

M = 375.21

Monoclinic,

a = 8.2798 (2) Å

b = 22.1975 (5) Å

c = 9.2537 (2) Å

β = 99.857 (2)°

V = 1675.64 (7) Å3

Z = 4

Mo Kα radiation

μ = 2.47 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII area–detector diffractometer

16035 measured reflections

4185 independent reflections

2619 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.116

S = 0.99

4185 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.68 e Å−3

Δρmin = −0.53 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811047520/bt5689sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047520/bt5689Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811047520/bt5689Isup3.cml

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

C18H15BrO4	F(000) = 760
Mr = 375.21	Dx = 1.487 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4185 reflections
a = 8.2798 (2) Å	θ = 1.8–28.5°
b = 22.1975 (5) Å	µ = 2.47 mm−1
c = 9.2537 (2) Å	T = 293 K
β = 99.857 (2)°	Block, colourless
V = 1675.64 (7) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Bruker SMART APEXII area–detector diffractometer	2619 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
graphite	θmax = 28.5°, θmin = 1.8°
ω and φ scans	h = −10→11
16035 measured reflections	k = −29→28
4185 independent reflections	l = −12→11

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0511P)2 + 0.7565P] where P = (Fo2 + 2Fc2)/3
4185 reflections	(Δ/σ)max = 0.003
209 parameters	Δρmax = 0.68 e Å−3
0 restraints	Δρmin = −0.53 e Å−3

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
C1	−0.0256 (5)	0.60472 (17)	0.2844 (4)	0.0795 (10)
H1	−0.0073	0.5836	0.2019	0.095*
C2	−0.0193 (4)	0.66597 (16)	0.2866 (3)	0.0742 (9)
H2	−0.0004	0.6868	0.2038	0.089*
C3	−0.0407 (4)	0.69756 (13)	0.4103 (3)	0.0626 (7)
H3	−0.0367	0.7394	0.4098	0.075*
C4	−0.0678 (3)	0.66781 (12)	0.5351 (3)	0.0528 (6)
C5	−0.0808 (5)	0.60533 (13)	0.5282 (3)	0.0779 (10)
H5	−0.1045	0.5841	0.6087	0.093*
C6	−0.0590 (5)	0.57457 (16)	0.4040 (4)	0.0914 (12)
H6	−0.0671	0.5328	0.4017	0.110*
C7	−0.0852 (4)	0.69664 (11)	0.6740 (3)	0.0541 (7)
H7	−0.1372	0.6730	0.7353	0.065*
C8	−0.0393 (3)	0.75109 (11)	0.7281 (3)	0.0488 (6)
C9	−0.0742 (4)	0.76453 (12)	0.8777 (3)	0.0549 (7)
C10	−0.0620 (6)	0.83736 (17)	1.0636 (3)	0.0921 (12)
H10A	−0.1780	0.8396	1.0627	0.138*
H10B	−0.0132	0.8760	1.0891	0.138*
H10C	−0.0145	0.8080	1.1343	0.138*
C11	0.0460 (3)	0.79772 (11)	0.6525 (3)	0.0478 (6)
H11A	0.1082	0.8246	0.7238	0.057*
H11B	0.1208	0.7788	0.5964	0.057*
C12	−0.0297 (3)	0.87741 (10)	0.4790 (2)	0.0408 (5)
C13	0.1324 (3)	0.88866 (11)	0.4670 (3)	0.0473 (6)
H13	0.2153	0.8639	0.5147	0.057*
C14	0.1704 (3)	0.93657 (11)	0.3844 (3)	0.0506 (6)
H14	0.2791	0.9442	0.3769	0.061*
C15	0.0484 (4)	0.97320 (10)	0.3130 (3)	0.0493 (6)
C16	−0.1114 (3)	0.96307 (11)	0.3251 (3)	0.0494 (6)
H16	−0.1930	0.9884	0.2774	0.059*
C17	−0.1526 (3)	0.91524 (10)	0.4083 (3)	0.0435 (5)
C18	−0.3232 (4)	0.90698 (15)	0.4253 (3)	0.0644 (8)
H18	−0.3488	0.8737	0.4782	0.077*
O1	−0.1327 (3)	0.73006 (10)	0.9529 (2)	0.0864 (8)
O2	−0.0325 (3)	0.82006 (9)	0.9198 (2)	0.0700 (6)
O3	−0.0789 (2)	0.83086 (7)	0.55632 (19)	0.0498 (4)
O4	−0.4327 (3)	0.94054 (12)	0.3751 (3)	0.0897 (7)
Br1	0.10355 (5)	1.038580 (15)	0.19991 (4)	0.08254 (17)

	U11	U22	U33	U12	U13	U23
C1	0.093 (3)	0.084 (2)	0.0561 (19)	0.0222 (19)	−0.0031 (16)	−0.0179 (17)
C2	0.090 (2)	0.083 (2)	0.0484 (17)	0.0013 (19)	0.0090 (15)	0.0005 (15)
C3	0.083 (2)	0.0534 (16)	0.0505 (15)	−0.0011 (14)	0.0078 (14)	−0.0005 (12)
C4	0.0624 (17)	0.0469 (14)	0.0469 (14)	−0.0033 (12)	0.0034 (12)	0.0009 (11)
C5	0.125 (3)	0.0500 (17)	0.0551 (18)	−0.0120 (17)	0.0043 (17)	−0.0015 (14)
C6	0.143 (4)	0.056 (2)	0.066 (2)	0.012 (2)	−0.010 (2)	−0.0116 (16)
C7	0.0684 (19)	0.0458 (14)	0.0495 (14)	−0.0071 (12)	0.0141 (12)	0.0047 (11)
C8	0.0566 (16)	0.0437 (13)	0.0476 (13)	−0.0035 (11)	0.0126 (11)	0.0045 (11)
C9	0.0700 (19)	0.0470 (15)	0.0491 (15)	−0.0082 (13)	0.0141 (13)	0.0016 (12)
C10	0.147 (4)	0.075 (2)	0.0601 (19)	−0.021 (2)	0.035 (2)	−0.0209 (17)
C11	0.0503 (16)	0.0440 (13)	0.0501 (14)	−0.0012 (11)	0.0114 (11)	0.0056 (11)
C12	0.0467 (15)	0.0335 (11)	0.0447 (13)	−0.0030 (10)	0.0150 (10)	−0.0039 (9)
C13	0.0451 (16)	0.0412 (13)	0.0571 (15)	0.0036 (11)	0.0128 (11)	0.0012 (11)
C14	0.0508 (16)	0.0453 (13)	0.0597 (16)	−0.0075 (12)	0.0210 (12)	−0.0054 (12)
C15	0.0695 (19)	0.0361 (12)	0.0449 (13)	−0.0085 (12)	0.0172 (12)	−0.0047 (10)
C16	0.0603 (18)	0.0421 (13)	0.0450 (14)	0.0045 (12)	0.0066 (11)	−0.0011 (11)
C17	0.0449 (15)	0.0411 (12)	0.0446 (13)	−0.0008 (10)	0.0083 (10)	−0.0050 (10)
C18	0.0521 (19)	0.0700 (19)	0.0709 (19)	−0.0001 (15)	0.0103 (14)	0.0036 (15)
O1	0.142 (2)	0.0641 (13)	0.0643 (13)	−0.0322 (13)	0.0482 (14)	−0.0047 (10)
O2	0.1062 (17)	0.0520 (11)	0.0564 (11)	−0.0188 (11)	0.0268 (11)	−0.0088 (9)
O3	0.0457 (10)	0.0423 (9)	0.0627 (11)	−0.0029 (7)	0.0129 (8)	0.0106 (8)
O4	0.0473 (13)	0.1048 (18)	0.115 (2)	0.0144 (13)	0.0078 (12)	0.0127 (16)
Br1	0.1225 (4)	0.0595 (2)	0.0689 (2)	−0.02273 (18)	0.0257 (2)	0.01451 (15)

C1—C2	1.361 (5)	C10—H10B	0.9600
C1—C6	1.361 (5)	C10—H10C	0.9600
C1—H1	0.9300	C11—O3	1.445 (3)
C2—C3	1.380 (4)	C11—H11A	0.9700
C2—H2	0.9300	C11—H11B	0.9700
C3—C4	1.381 (4)	C12—O3	1.359 (3)
C3—H3	0.9300	C12—C13	1.389 (3)
C4—C5	1.392 (4)	C12—C17	1.393 (3)
C4—C7	1.466 (4)	C13—C14	1.377 (3)
C5—C6	1.375 (5)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.374 (4)
C6—H6	0.9300	C14—H14	0.9300
C7—C8	1.338 (4)	C15—C16	1.366 (4)
C7—H7	0.9300	C15—Br1	1.890 (2)
C8—C9	1.492 (4)	C16—C17	1.388 (3)
C8—C11	1.493 (3)	C16—H16	0.9300
C9—O1	1.192 (3)	C17—C18	1.459 (4)
C9—O2	1.321 (3)	C18—O4	1.204 (4)
C10—O2	1.446 (3)	C18—H18	0.9300
C10—H10A	0.9600
C2—C1—C6	119.4 (3)	H10A—C10—H10C	109.5
C2—C1—H1	120.3	H10B—C10—H10C	109.5
C6—C1—H1	120.3	O3—C11—C8	107.2 (2)
C1—C2—C3	120.7 (3)	O3—C11—H11A	110.3
C1—C2—H2	119.7	C8—C11—H11A	110.3
C3—C2—H2	119.7	O3—C11—H11B	110.3
C2—C3—C4	120.9 (3)	C8—C11—H11B	110.3
C2—C3—H3	119.6	H11A—C11—H11B	108.5
C4—C3—H3	119.6	O3—C12—C13	124.1 (2)
C3—C4—C5	117.4 (3)	O3—C12—C17	116.4 (2)
C3—C4—C7	125.4 (2)	C13—C12—C17	119.5 (2)
C5—C4—C7	117.2 (2)	C14—C13—C12	119.9 (2)
C6—C5—C4	120.9 (3)	C14—C13—H13	120.0
C6—C5—H5	119.6	C12—C13—H13	120.0
C4—C5—H5	119.6	C15—C14—C13	120.3 (2)
C1—C6—C5	120.6 (3)	C15—C14—H14	119.8
C1—C6—H6	119.7	C13—C14—H14	119.9
C5—C6—H6	119.7	C16—C15—C14	120.4 (2)
C8—C7—C4	131.1 (2)	C16—C15—Br1	120.1 (2)
C8—C7—H7	114.4	C14—C15—Br1	119.5 (2)
C4—C7—H7	114.4	C15—C16—C17	120.3 (2)
C7—C8—C9	116.1 (2)	C15—C16—H16	119.8
C7—C8—C11	125.3 (2)	C17—C16—H16	119.8
C9—C8—C11	118.6 (2)	C16—C17—C12	119.5 (2)
O1—C9—O2	122.6 (2)	C16—C17—C18	119.4 (2)
O1—C9—C8	125.2 (2)	C12—C17—C18	121.1 (2)
O2—C9—C8	112.2 (2)	O4—C18—C17	124.1 (3)
O2—C10—H10A	109.5	O4—C18—H18	118.0
O2—C10—H10B	109.5	C17—C18—H18	118.0
H10A—C10—H10B	109.5	C9—O2—C10	116.2 (2)
O2—C10—H10C	109.5	C12—O3—C11	117.67 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3	0.93	2.50	3.290 (3)	143.
C7—H7···O1	0.93	2.37	2.777 (3)	106.
C11—H11A···O2	0.97	2.32	2.708 (3)	103.
C18—H18···O3	0.93	2.42	2.752 (4)	101.
C2—H2···O1i	0.93	2.58	3.383 (4)	145.
C13—H13···O1ii	0.93	2.55	3.291 (3)	137.
C14—H14···O4iii	0.93	2.39	3.302 (4)	167.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3	0.93	2.50	3.290 (3)	143
C2—H2⋯O1i	0.93	2.58	3.383 (4)	145
C13—H13⋯O1ii	0.93	2.55	3.291 (3)	137
C14—H14⋯O4iii	0.93	2.39	3.302 (4)	167

Symmetry codes: (i) ; (ii) ; (iii) .