(E)-Methyl 2-[(4-bromo-2-formyl­phen­oxy)meth­yl]-3-phenyl­acrylate

Anuradha, T.; Sivakumar, G.; Seshadri, P.R.; Bakthadoss, M.

doi:10.1107/S1600536811047520

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3322

https://doi.org/10.1107/S1600536811047520

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(E)-Methyl 2-[(4-bromo-2-formylphenoxy)methyl]-3-phenylacrylate

T. Anuradha,^a G. Sivakumar,^b P. R. Seshadri ^a ^* and M. Bakthadoss ^b

^aPost Graduate & Research Department of Physics, Agurchand Manmull Jain College, Chennai 600 114, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: seshadri_pr@yahoo.com

(Received 24 October 2011; accepted 9 November 2011; online 16 November 2011)

The C=C double bond in the title compound, C₁₈H₁₅BrO₄, adopts an E configuration. The two rings are almost orthogonal to each other, making a dihedral angle of 82.8 (1)°. An intramolecular C—H⋯O hydrogen bond occurs. The crystal structure is stabilized by intermolecular 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_r = 375.21
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.116
S = 0.99
4185 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.53 e Å⁻³

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) x, y, z-1; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x+1, y, z.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811047520/bt5689sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811047520/bt5689Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811047520/bt5689Isup3.cml

checkCIF report

Comment top

The title compound is used as precursor to obtain the desired tetra cyclic chromenopyran pyrimidinedione compounds via a tandem Knoevenagel intra-molecular hetero-Diels-Alder reaction (Bakthadoss et al., 2009). Cinnamic acid and its derivatives including esters and carboxylic functional derivatives are used as important components in flavours, perfumes, synthetic indigo and pharmaceuticals. Cinnamate can act as optical filters or deactivate substrate molecules that have been excited by light for the protection polymers and organic substances. They are used as cosmetic grades and as sunscreen agents to reduce skin damage by blocking UV—A, B (Sharma, 2011). In view of this medicinal importance, the crystal structure determination of the title compound was carried out and the results are presented here.

The molecule adopts an E configuration about the C7 ═ C8 double bond. The dihedral angle between the best planes through the bromo-formylphenoxy group (C11—C18/O3/O4/Br) and phenylacrylate group (C1—C10/O1/O2) is 82.8 (1)°. The formyl group (C18/H18/04) is axial to the plane of the benzene ring to which it is attached as evidenced by the torsion angle C18—O4— C17— C12 of -7.9 (1)°.

From the bond length and bond angle analysis of the compound, the conformation of phenylacrylate group are comparable with corresponding values for the structure of ((E) – methyl 3-(3,4– dihydroxyphenyl)acrylate (Wang et al., 2011).

The crystal packing is stabilized by intramolecular and intermolecular C—H···O hydrogen bonding interaction (Table 1).

Related literature top

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 top

A solution of 5-bromo-2-hydroxybenzaldehyde (1.0 mmol, 0.201 g) and potassium carbonate (2.0 mmol, 0.2293 g) in acetonitrile solvent (5 ml) was stirred for 15 minute at room temperature. To this solution, (Z)-methyl2-(bromomethyl)-3-phenylacrylate (1.2 mmol, 0.25 g) was added dropwise. After the completion of the reaction, as indicated by TLC, acetonitrile was evaporated. EtOAc (15 ml) and water (15 ml) were added to the crude mass. The organic layer was dried over anhydrous sodium sulfate. Removal of solvent led to the crude product, which was purified through pad of silica gel (100–200mesh) using ethylacetate and hexanes(1:9) as solvents. The pure title compound was obtained as a colourless solid (0.31 g, 83% yield). Recrystallization was carried out using ethylacetate as solvent.

Structure description top

The crystal packing is stabilized by intramolecular and intermolecular C—H···O hydrogen bonding interaction (Table 1).

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).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. Packing of the molecule down b axis

(E)-Methyl 2-[(4-bromo-2-formylphenoxy)methyl]-3-phenylacrylate top

Crystal data top

C₁₈H₁₅BrO₄	F(000) = 760
M_r = 375.21	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0511P)² + 0.7565P] where P = (F_o² + 2F_c²)/3
4185 reflections	(Δ/σ)_max = 0.003
209 parameters	Δρ_max = 0.68 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

C₁₈H₁₅BrO₄	V = 1675.64 (7) Å³
M_r = 375.21	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.2798 (2) Å	µ = 2.47 mm⁻¹
b = 22.1975 (5) Å	T = 293 K
c = 9.2537 (2) Å	0.20 × 0.20 × 0.20 mm
β = 99.857 (2)°

Data collection top

Bruker SMART APEXII area–detector diffractometer	2619 reflections with I > 2σ(I)
16035 measured reflections	R_int = 0.033
4185 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 0.99	Δρ_max = 0.68 e Å⁻³
4185 reflections	Δρ_min = −0.53 e Å⁻³
209 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x, y, z−1; (ii) x+1/2, −y+3/2, z−1/2; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₅BrO₄
M_r	375.21
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	8.2798 (2), 22.1975 (5), 9.2537 (2)
β (°)	99.857 (2)
V (Å³)	1675.64 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.47
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII area–detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16035, 4185, 2619
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.116, 0.99
No. of reflections	4185
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.53

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3	0.93	2.50	3.290 (3)	143.2
C7—H7···O1	0.93	2.37	2.777 (3)	105.9
C11—H11A···O2	0.97	2.32	2.708 (3)	103.1
C18—H18···O3	0.93	2.42	2.752 (4)	100.7
C2—H2···O1ⁱ	0.93	2.58	3.383 (4)	145.2
C13—H13···O1ⁱⁱ	0.93	2.55	3.291 (3)	136.9
C14—H14···O4ⁱⁱⁱ	0.93	2.39	3.302 (4)	167.0

Symmetry codes: (i) x, y, z−1; (ii) x+1/2, −y+3/2, z−1/2; (iii) x+1, y, z.

Acknowledgements

BB thanks the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection.

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