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

In the title compound, C(19)H(17)BrO(4), the dihedral angle between the two benzene rings is 82.9 (2)°. The mol-ecular structure is stabilized by an intra-molecular C-H⋯O hydrogen bond, which generates an S(7) ring motif. The crystal packing is stabilized by C-H⋯O hydrogen bonds, which generate two centrosymmetic ring systems with R(2) (2)(18) and R(2) (2)(14) graph-set motifs. The crystal packing is further stabilized by inter-molecular π-π inter-actions [centroid-centroid distance = 3.984 (2) Å].

Related literature

For background to the applications of acrylates, see: de Fraine & Martin (1991 ▶); Zhang & Ji (1992 ▶). For related structures, see: Wang et al. (2011 ▶); Vijayakumar et al. (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C19H17BrO4

M = 389.24

Triclinic,

a = 7.9262 (4) Å

b = 8.9078 (5) Å

c = 13.2331 (6) Å

α = 74.387 (3)°

β = 83.593 (2)°

γ = 75.770 (3)°

V = 871.20 (8) Å3

Z = 2

Mo Kα radiation

μ = 2.38 mm−1

T = 293 K

0.25 × 0.23 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.546, T max = 0.652

15446 measured reflections

3386 independent reflections

2419 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.121

S = 1.01

3386 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); 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) global, I. DOI: 10.1107/S1600536812006630/bt5816sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006630/bt5816Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812006630/bt5816Isup3.cml

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

C19H17BrO4	Z = 2
Mr = 389.24	F(000) = 396
Triclinic, P1	Dx = 1.484 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9262 (4) Å	Cell parameters from 3452 reflections
b = 8.9078 (5) Å	θ = 1.6–26.1°
c = 13.2331 (6) Å	µ = 2.38 mm−1
α = 74.387 (3)°	T = 293 K
β = 83.593 (2)°	Block, colourless
γ = 75.770 (3)°	0.25 × 0.23 × 0.18 mm
V = 871.20 (8) Å3

Bruker APEXII CCD diffractometer	3386 independent reflections
Radiation source: fine-focus sealed tube	2419 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
Detector resolution: 10.0 pixels mm-1	θmax = 26.1°, θmin = 2.4°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→10
Tmin = 0.546, Tmax = 0.652	l = −16→16
15446 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0704P)2 + 0.2283P] where P = (Fo2 + 2Fc2)/3
3386 reflections	(Δ/σ)max = 0.001
219 parameters	Δρmax = 0.67 e Å−3
0 restraints	Δρmin = −0.41 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	−0.0190 (3)	0.1409 (3)	0.0632 (2)	0.0436 (6)
C2	−0.0529 (4)	0.2719 (3)	−0.0228 (2)	0.0492 (7)
H2	−0.1652	0.3118	−0.0466	0.059*
C3	0.0793 (4)	0.3418 (3)	−0.0723 (2)	0.0530 (8)
C4	0.2463 (4)	0.2851 (3)	−0.0381 (2)	0.0521 (7)
H4	0.3347	0.3345	−0.0727	0.063*
C5	0.2831 (4)	0.1550 (3)	0.0472 (2)	0.0476 (7)
H5	0.3958	0.1169	0.0706	0.057*
C6	0.1509 (3)	0.0820 (3)	0.0978 (2)	0.0400 (6)
C7	0.3452 (3)	−0.1066 (3)	0.2212 (2)	0.0463 (7)
H7A	0.3805	−0.0227	0.2418	0.056*
H7B	0.4283	−0.1395	0.1673	0.056*
C8	0.3425 (4)	−0.2459 (3)	0.3141 (2)	0.0491 (7)
C9	0.3846 (4)	−0.4096 (4)	0.2990 (3)	0.0568 (8)
C10	0.4617 (6)	−0.5711 (5)	0.1796 (3)	0.0814 (11)
H10A	0.5751	−0.6240	0.2056	0.122*
H10B	0.4643	−0.5618	0.1055	0.122*
H10C	0.3785	−0.6322	0.2151	0.122*
C11	−0.1608 (4)	0.0680 (4)	0.1180 (3)	0.0555 (8)
H11	−0.1325	−0.0241	0.1721	0.067*
C12	0.3161 (4)	−0.2336 (4)	0.4127 (2)	0.0556 (8)
H12	0.3271	−0.3307	0.4630	0.067*
C13	0.2727 (4)	−0.0931 (4)	0.4554 (2)	0.0512 (7)
C14	0.1771 (4)	0.0561 (4)	0.4051 (2)	0.0577 (8)
H14	0.1347	0.0708	0.3395	0.069*
C15	0.1444 (4)	0.1815 (4)	0.4507 (3)	0.0638 (9)
H15	0.0807	0.2805	0.4151	0.077*
C16	0.2035 (4)	0.1652 (4)	0.5481 (3)	0.0613 (8)
C17	0.2973 (4)	0.0179 (4)	0.5982 (3)	0.0651 (9)
H17	0.3392	0.0042	0.6637	0.078*
C18	0.3305 (4)	−0.1087 (4)	0.5544 (3)	0.0627 (8)
H18	0.3929	−0.2076	0.5911	0.075*
C19	0.1688 (6)	0.3035 (5)	0.5977 (3)	0.0875 (12)
H19A	0.1914	0.2644	0.6711	0.131*
H19B	0.0493	0.3601	0.5898	0.131*
H19C	0.2435	0.3744	0.5641	0.131*
Br1	0.03444 (6)	0.52045 (4)	−0.19017 (3)	0.0788 (2)
O1	0.3943 (5)	−0.5289 (3)	0.3685 (2)	0.0984 (9)
O2	0.4125 (3)	−0.4137 (3)	0.19867 (17)	0.0616 (6)
O3	0.1745 (2)	−0.0481 (2)	0.18098 (15)	0.0472 (5)
O4	−0.3117 (3)	0.1191 (3)	0.0979 (2)	0.0792 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0456 (16)	0.0445 (15)	0.0437 (15)	−0.0063 (12)	−0.0056 (12)	−0.0183 (12)
C2	0.0560 (17)	0.0468 (16)	0.0461 (16)	−0.0008 (14)	−0.0123 (14)	−0.0195 (13)
C3	0.079 (2)	0.0398 (15)	0.0375 (15)	−0.0019 (15)	−0.0099 (15)	−0.0129 (12)
C4	0.0628 (19)	0.0461 (16)	0.0462 (16)	−0.0129 (14)	0.0038 (14)	−0.0114 (13)
C5	0.0452 (16)	0.0483 (16)	0.0493 (16)	−0.0105 (13)	−0.0031 (13)	−0.0121 (13)
C6	0.0464 (16)	0.0381 (14)	0.0377 (13)	−0.0084 (12)	−0.0045 (12)	−0.0131 (11)
C7	0.0401 (15)	0.0445 (16)	0.0497 (16)	−0.0047 (12)	−0.0049 (12)	−0.0076 (13)
C8	0.0465 (16)	0.0432 (16)	0.0522 (17)	−0.0058 (12)	−0.0060 (13)	−0.0053 (13)
C9	0.065 (2)	0.0443 (17)	0.0537 (18)	−0.0052 (14)	−0.0029 (15)	−0.0060 (14)
C10	0.105 (3)	0.060 (2)	0.082 (3)	−0.013 (2)	−0.005 (2)	−0.029 (2)
C11	0.0481 (19)	0.061 (2)	0.0616 (19)	−0.0093 (15)	−0.0014 (15)	−0.0259 (16)
C12	0.0605 (19)	0.0479 (17)	0.0505 (18)	−0.0071 (14)	−0.0080 (14)	−0.0016 (14)
C13	0.0554 (18)	0.0500 (17)	0.0438 (16)	−0.0113 (14)	0.0004 (13)	−0.0060 (13)
C14	0.064 (2)	0.0572 (19)	0.0470 (17)	−0.0053 (15)	−0.0085 (15)	−0.0100 (14)
C15	0.075 (2)	0.0523 (19)	0.0557 (19)	−0.0021 (16)	−0.0047 (16)	−0.0106 (15)
C16	0.064 (2)	0.066 (2)	0.0539 (19)	−0.0175 (17)	0.0086 (16)	−0.0187 (16)
C17	0.068 (2)	0.083 (3)	0.0450 (17)	−0.0144 (18)	−0.0014 (15)	−0.0196 (17)
C18	0.067 (2)	0.064 (2)	0.0445 (17)	−0.0026 (16)	−0.0013 (15)	−0.0045 (15)
C19	0.105 (3)	0.088 (3)	0.078 (3)	−0.020 (2)	0.006 (2)	−0.040 (2)
Br1	0.1216 (4)	0.0559 (3)	0.0471 (2)	−0.0034 (2)	−0.01539 (19)	−0.00359 (15)
O1	0.167 (3)	0.0439 (14)	0.0661 (16)	−0.0054 (15)	−0.0002 (17)	−0.0025 (12)
O2	0.0770 (15)	0.0477 (12)	0.0569 (13)	−0.0091 (10)	−0.0040 (11)	−0.0118 (10)
O3	0.0432 (11)	0.0475 (11)	0.0476 (11)	−0.0118 (8)	−0.0073 (8)	−0.0031 (9)
O4	0.0420 (13)	0.098 (2)	0.101 (2)	−0.0105 (12)	−0.0076 (13)	−0.0351 (16)

C1—C2	1.388 (4)	C10—H10A	0.9600
C1—C6	1.399 (4)	C10—H10B	0.9600
C1—C11	1.461 (4)	C10—H10C	0.9600
C2—C3	1.365 (4)	C11—O4	1.203 (4)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.376 (4)	C12—C13	1.459 (4)
C3—Br1	1.898 (3)	C12—H12	0.9300
C4—C5	1.381 (4)	C13—C14	1.387 (4)
C4—H4	0.9300	C13—C18	1.396 (4)
C5—C6	1.383 (4)	C14—C15	1.366 (5)
C5—H5	0.9300	C14—H14	0.9300
C6—O3	1.357 (3)	C15—C16	1.380 (5)
C7—O3	1.432 (3)	C15—H15	0.9300
C7—C8	1.496 (4)	C16—C17	1.369 (5)
C7—H7A	0.9700	C16—C19	1.501 (5)
C7—H7B	0.9700	C17—C18	1.360 (5)
C8—C12	1.328 (4)	C17—H17	0.9300
C8—C9	1.477 (4)	C18—H18	0.9300
C9—O1	1.196 (4)	C19—H19A	0.9600
C9—O2	1.330 (4)	C19—H19B	0.9600
C10—O2	1.442 (4)	C19—H19C	0.9600
C2—C1—C6	119.4 (3)	H10A—C10—H10C	109.5
C2—C1—C11	120.0 (3)	H10B—C10—H10C	109.5
C6—C1—C11	120.6 (3)	O4—C11—C1	124.4 (3)
C3—C2—C1	119.7 (3)	O4—C11—H11	117.8
C3—C2—H2	120.1	C1—C11—H11	117.8
C1—C2—H2	120.1	C8—C12—C13	130.8 (3)
C2—C3—C4	121.1 (3)	C8—C12—H12	114.6
C2—C3—Br1	120.1 (2)	C13—C12—H12	114.6
C4—C3—Br1	118.9 (2)	C14—C13—C18	117.1 (3)
C3—C4—C5	120.2 (3)	C14—C13—C12	124.8 (3)
C3—C4—H4	119.9	C18—C13—C12	118.1 (3)
C5—C4—H4	119.9	C15—C14—C13	120.8 (3)
C4—C5—C6	119.5 (3)	C15—C14—H14	119.6
C4—C5—H5	120.3	C13—C14—H14	119.6
C6—C5—H5	120.3	C14—C15—C16	121.7 (3)
O3—C6—C5	123.9 (2)	C14—C15—H15	119.1
O3—C6—C1	116.0 (2)	C16—C15—H15	119.1
C5—C6—C1	120.1 (3)	C17—C16—C15	117.6 (3)
O3—C7—C8	109.0 (2)	C17—C16—C19	120.8 (3)
O3—C7—H7A	109.9	C15—C16—C19	121.7 (3)
C8—C7—H7A	109.9	C18—C17—C16	121.6 (3)
O3—C7—H7B	109.9	C18—C17—H17	119.2
C8—C7—H7B	109.9	C16—C17—H17	119.2
H7A—C7—H7B	108.3	C17—C18—C13	121.2 (3)
C12—C8—C9	116.4 (3)	C17—C18—H18	119.4
C12—C8—C7	123.8 (3)	C13—C18—H18	119.4
C9—C8—C7	119.6 (3)	C16—C19—H19A	109.5
O1—C9—O2	121.9 (3)	C16—C19—H19B	109.5
O1—C9—C8	124.7 (3)	H19A—C19—H19B	109.5
O2—C9—C8	113.4 (3)	C16—C19—H19C	109.5
O2—C10—H10A	109.5	H19A—C19—H19C	109.5
O2—C10—H10B	109.5	H19B—C19—H19C	109.5
H10A—C10—H10B	109.5	C9—O2—C10	115.7 (3)
O2—C10—H10C	109.5	C6—O3—C7	117.3 (2)
C6—C1—C2—C3	−0.2 (4)	C6—C1—C11—O4	174.2 (3)
C11—C1—C2—C3	178.5 (3)	C9—C8—C12—C13	−180.0 (3)
C1—C2—C3—C4	−0.3 (4)	C7—C8—C12—C13	5.0 (5)
C1—C2—C3—Br1	179.79 (19)	C8—C12—C13—C14	30.2 (5)
C2—C3—C4—C5	0.2 (4)	C8—C12—C13—C18	−150.1 (3)
Br1—C3—C4—C5	−179.8 (2)	C18—C13—C14—C15	1.0 (5)
C3—C4—C5—C6	0.3 (4)	C12—C13—C14—C15	−179.3 (3)
C4—C5—C6—O3	178.7 (3)	C13—C14—C15—C16	−0.4 (5)
C4—C5—C6—C1	−0.7 (4)	C14—C15—C16—C17	0.1 (5)
C2—C1—C6—O3	−178.8 (2)	C14—C15—C16—C19	179.5 (3)
C11—C1—C6—O3	2.5 (4)	C15—C16—C17—C18	−0.5 (5)
C2—C1—C6—C5	0.7 (4)	C19—C16—C17—C18	−179.8 (3)
C11—C1—C6—C5	−178.0 (3)	C16—C17—C18—C13	1.1 (5)
O3—C7—C8—C12	−93.5 (3)	C14—C13—C18—C17	−1.4 (5)
O3—C7—C8—C9	91.6 (3)	C12—C13—C18—C17	178.9 (3)
C12—C8—C9—O1	0.9 (5)	O1—C9—O2—C10	−2.4 (5)
C7—C8—C9—O1	176.2 (3)	C8—C9—O2—C10	177.4 (3)
C12—C8—C9—O2	−178.9 (3)	C5—C6—O3—C7	3.3 (4)
C7—C8—C9—O2	−3.6 (4)	C1—C6—O3—C7	−177.2 (2)
C2—C1—C11—O4	−4.5 (4)	C8—C7—O3—C6	178.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O3	0.93	2.55	3.341 (3)	143
C4—H4···O2i	0.93	2.57	3.474 (4)	164
C18—H18···O1ii	0.93	2.49	3.388 (4)	161
C5—H5···O4iii	0.93	2.39	3.276 (4)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O3	0.93	2.55	3.341 (3)	143
C4—H4⋯O2i	0.93	2.57	3.474 (4)	164
C18—H18⋯O1ii	0.93	2.49	3.388 (4)	161
C5—H5⋯O4iii	0.93	2.39	3.276 (4)	159

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