Ethyl 2-(4-chloro­phen­yl)-3-(3,5-dimethoxy­phen­oxy)acrylate

Chen, W.; Pan, F.; Chen, W.; Xia, D.-S.; Zeng, Q.-F.

doi:10.1107/S1600536808039263

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2471

doi:10.1107/S1600536808039263

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Ethyl 2-(4-chlorophenyl)-3-(3,5-dimethoxyphenoxy)acrylate

Wu Chen,^a Yong-Ming Cui,^a Fei Pan,^a Dong-Sheng Xia ^a and Qing-Fu Zeng ^a ^*

^aEngineering Research Center for Clean Production of Textile Printing, Ministry of Education, Wuhan University of Science & Engineering, Wuhan 430073, People's Republic of China
^*Correspondence e-mail: qingfu_zeng@163.com

(Received 31 October 2008; accepted 21 November 2008; online 29 November 2008)

The title compound, C₁₉H₁₉ClO₅, displays a dihedral angle of 74.7 (3)° between the mean planes of the 4-chlorophenyl and phenol rings.

Related literature

For phenylacetate and styrene derivatives, see: Fang et al. (2007 ); Huang et al. (2007 ); Li et al. (2007 ).

Experimental

Crystal data

C₁₉H₁₉ClO₅
M_r = 362.80
Triclinic, $[P \overline 1]$
a = 9.601 (2) Å
b = 9.607 (3) Å
c = 10.368 (2) Å
α = 77.84 (2)°
β = 75.42 (3)°
γ = 87.40 (3)°
V = 904.7 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 298 (2) K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.932, T_max = 0.977
6132 measured reflections
3280 independent reflections
2153 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.147
S = 1.03
3280 reflections
230 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039263/su2078sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808039263/su2078Isup2.hkl

checkCIF report

Comment top

Phenylacetate and styrene derivatives are important for their extensive biological activities. Recently a large number of such compounds have been synthesized, and found to have good biological activities (Fang et al., 2007; Huang et al., 2007; Li et al., 2007). Here report on the crystal structure of the new acrylate compound, (I).

The molecular structure of compound (I) is illustrated in Fig. 1. All the bond lengths and angles are within normal values. The dihedral angle between the mean plane of the 4-chlorophenyl ring (C1—C6) and the mean plane through the phenol ring (C7—C12) is 74.7 (3)°. The [O5/C13—C15/O1/O2] mean plane forms dihedral angles of 23.6 (3)° and 59.6 (3)° with the mean planes of rings (C1—C6) and (C7—C12), respectively.

In the crystal structure the molecules stack head-to-head along the c direction.

Related literature top

For phenylacetate and styrene derivatives, see: Fang et al. (2007); Huang et al. (2007); Li et al. (2007).

Experimental top

Ethyl 3-bromo-2-(4-chlorophenyl)acrylate (0.1 mmol) and 3,5-dimethoxyphenol (0.1 mmol) were reacted in chloroform for 12 h, giving a clear colorless solution. Crytals of compound (I) were formed by gradual evaporation of the solution.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of compound (I), showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probabilty level.

Ethyl 2-(4-chlorophenyl)-3-(3,5-dimethoxyphenoxy)acrylate top

Crystal data top

C₁₉H₁₉ClO₅	Z = 2
M_r = 362.80	F(000) = 382
Triclinic, P1	D_x = 1.335 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.601 (2) Å	Cell parameters from 1273 reflections
b = 9.607 (3) Å	θ = 2.4–25.3°
c = 10.368 (2) Å	µ = 0.24 mm⁻¹
α = 77.84 (2)°	T = 298 K
β = 75.42 (3)°	Block, colorless
γ = 87.40 (3)°	0.30 × 0.20 × 0.10 mm
V = 904.7 (4) Å³

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3280 independent reflections
Radiation source: fine-focus sealed tube	2153 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 25.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
T_min = 0.932, T_max = 0.977	k = −11→11
6132 measured reflections	l = −12→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.058	H-atom parameters constrained
wR(F²) = 0.147	w = 1/[σ²(F_o²) + (0.0584P)² + 0.3443P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3280 reflections	Δρ_max = 0.48 e Å⁻³
230 parameters	Δρ_min = −0.40 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (3)

Crystal data top

C₁₉H₁₉ClO₅	γ = 87.40 (3)°
M_r = 362.80	V = 904.7 (4) Å³
Triclinic, P1	Z = 2
a = 9.601 (2) Å	Mo Kα radiation
b = 9.607 (3) Å	µ = 0.24 mm⁻¹
c = 10.368 (2) Å	T = 298 K
α = 77.84 (2)°	0.30 × 0.20 × 0.10 mm
β = 75.42 (3)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3280 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2153 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.977	R_int = 0.028
6132 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.147	H-atom parameters constrained
S = 1.03	Δρ_max = 0.48 e Å⁻³
3280 reflections	Δρ_min = −0.40 e Å⁻³
230 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	0.9387 (3)	0.1311 (3)	0.7046 (3)	0.0377 (7)
C2	1.0552 (3)	0.1122 (3)	0.5995 (3)	0.0393 (7)
H2	1.0797	0.1812	0.5197	0.047*
C3	1.1345 (3)	−0.0115 (3)	0.6159 (3)	0.0411 (7)
C4	1.0993 (3)	−0.1153 (3)	0.7352 (3)	0.0433 (8)
H4	1.1517	−0.1990	0.7447	0.052*
C5	0.9853 (3)	−0.0911 (3)	0.8389 (3)	0.0399 (7)
C6	0.9046 (3)	0.0313 (3)	0.8241 (3)	0.0424 (7)
H6	0.8276	0.0461	0.8947	0.051*
C7	0.6961 (3)	0.5299 (3)	0.6619 (3)	0.0341 (7)
C8	0.5498 (3)	0.5569 (3)	0.6821 (3)	0.0429 (7)
H8	0.5004	0.5304	0.6245	0.051*
C9	0.4755 (3)	0.6225 (3)	0.7858 (3)	0.0476 (8)
H9	0.3773	0.6391	0.7982	0.057*
C10	0.5490 (3)	0.6624 (3)	0.8697 (3)	0.0442 (8)
C11	0.6936 (3)	0.6343 (3)	0.8557 (3)	0.0472 (8)
H11	0.7414	0.6591	0.9154	0.057*
C12	0.7665 (3)	0.5688 (3)	0.7519 (3)	0.0416 (7)
H12	0.8642	0.5503	0.7417	0.050*
C13	0.8483 (3)	0.3402 (3)	0.5672 (3)	0.0400 (7)
H13	0.8987	0.3089	0.4896	0.048*
C14	0.7768 (3)	0.4626 (3)	0.5486 (3)	0.0352 (7)
C15	0.7837 (3)	0.5296 (3)	0.4060 (3)	0.0378 (7)
C16	0.7084 (4)	0.7295 (3)	0.2597 (3)	0.0469 (8)
H16A	0.6915	0.6667	0.2031	0.056*
H16B	0.8017	0.7750	0.2182	0.056*
C17	0.5928 (4)	0.8392 (4)	0.2728 (4)	0.0638 (10)
H17A	0.5009	0.7929	0.3116	0.096*
H17B	0.5941	0.8959	0.1844	0.096*
H17C	0.6095	0.8993	0.3307	0.096*
C18	1.0305 (4)	−0.3072 (3)	0.9843 (3)	0.0595 (10)
H18A	1.0336	−0.3627	0.9167	0.089*
H18B	0.9906	−0.3639	1.0731	0.089*
H18C	1.1262	−0.2773	0.9788	0.089*
C19	1.2980 (4)	0.0648 (3)	0.3998 (3)	0.0580 (9)
H19A	1.2229	0.0832	0.3525	0.087*
H19B	1.3822	0.0325	0.3418	0.087*
H19C	1.3206	0.1506	0.4242	0.087*
Cl1	0.45938 (11)	0.75361 (11)	0.99503 (10)	0.0720 (4)
O5	0.8538 (3)	0.2570 (3)	0.6900 (3)	0.0694 (7)
O1	0.8506 (2)	0.4862 (2)	0.3068 (2)	0.0560 (6)
O2	0.7048 (2)	0.6494 (2)	0.39530 (19)	0.0412 (5)
O3	0.9429 (2)	−0.1850 (2)	0.9607 (2)	0.0501 (6)
O4	1.2510 (2)	−0.0425 (2)	0.5203 (2)	0.0545 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0428 (17)	0.0281 (15)	0.0451 (17)	0.0087 (13)	−0.0152 (14)	−0.0104 (13)
C2	0.0505 (19)	0.0275 (15)	0.0389 (16)	0.0037 (14)	−0.0133 (14)	−0.0030 (13)
C3	0.0410 (17)	0.0355 (16)	0.0457 (18)	0.0035 (14)	−0.0090 (14)	−0.0092 (14)
C4	0.0502 (19)	0.0317 (16)	0.0469 (18)	0.0087 (14)	−0.0154 (15)	−0.0037 (14)
C5	0.0468 (18)	0.0340 (16)	0.0392 (17)	0.0037 (14)	−0.0143 (14)	−0.0047 (13)
C6	0.0441 (18)	0.0400 (17)	0.0417 (17)	0.0064 (14)	−0.0088 (14)	−0.0085 (14)
C7	0.0346 (16)	0.0272 (14)	0.0382 (16)	0.0018 (12)	−0.0096 (13)	−0.0011 (12)
C8	0.0400 (18)	0.0495 (19)	0.0417 (17)	−0.0017 (14)	−0.0125 (14)	−0.0117 (14)
C9	0.0367 (17)	0.056 (2)	0.0488 (19)	0.0084 (15)	−0.0066 (15)	−0.0145 (16)
C10	0.051 (2)	0.0403 (17)	0.0370 (17)	0.0070 (15)	−0.0037 (15)	−0.0091 (14)
C11	0.053 (2)	0.0493 (19)	0.0432 (18)	0.0025 (16)	−0.0194 (15)	−0.0101 (15)
C12	0.0383 (17)	0.0409 (17)	0.0461 (17)	0.0061 (14)	−0.0136 (14)	−0.0073 (14)
C13	0.0464 (18)	0.0365 (17)	0.0361 (16)	0.0070 (14)	−0.0114 (14)	−0.0048 (13)
C14	0.0323 (16)	0.0321 (15)	0.0404 (16)	0.0037 (13)	−0.0078 (13)	−0.0078 (13)
C15	0.0351 (16)	0.0352 (16)	0.0441 (17)	0.0025 (13)	−0.0106 (14)	−0.0097 (13)
C16	0.059 (2)	0.0425 (18)	0.0396 (17)	0.0061 (16)	−0.0195 (16)	−0.0024 (14)
C17	0.082 (3)	0.053 (2)	0.066 (2)	0.0239 (19)	−0.038 (2)	−0.0124 (18)
C18	0.074 (2)	0.0423 (19)	0.053 (2)	0.0162 (18)	−0.0132 (18)	0.0046 (16)
C19	0.063 (2)	0.046 (2)	0.051 (2)	0.0065 (17)	0.0064 (17)	−0.0061 (16)
Cl1	0.0792 (7)	0.0803 (7)	0.0582 (6)	0.0120 (5)	−0.0040 (5)	−0.0363 (5)
O5	0.0825 (19)	0.0557 (15)	0.0689 (17)	0.0162 (14)	−0.0212 (14)	−0.0105 (13)
O1	0.0676 (16)	0.0554 (14)	0.0401 (12)	0.0240 (12)	−0.0068 (11)	−0.0121 (11)
O2	0.0476 (12)	0.0376 (11)	0.0373 (11)	0.0130 (10)	−0.0115 (9)	−0.0068 (9)
O3	0.0569 (14)	0.0403 (12)	0.0454 (12)	0.0099 (11)	−0.0100 (11)	0.0031 (10)
O4	0.0587 (15)	0.0414 (13)	0.0512 (13)	0.0129 (11)	0.0011 (11)	−0.0028 (11)

Geometric parameters (Å, º) top

C1—C6	1.373 (4)	C12—H12	0.9300
C1—C2	1.387 (4)	C13—C14	1.338 (4)
C1—O5	1.430 (3)	C13—O5	1.366 (4)
C2—C3	1.385 (4)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.469 (4)
C3—O4	1.363 (3)	C15—O1	1.212 (3)
C3—C4	1.392 (4)	C15—O2	1.349 (3)
C4—C5	1.378 (4)	C16—O2	1.446 (3)
C4—H4	0.9300	C16—C17	1.496 (4)
C5—O3	1.367 (3)	C16—H16A	0.9700
C5—C6	1.381 (4)	C16—H16B	0.9700
C6—H6	0.9300	C17—H17A	0.9600
C7—C8	1.388 (4)	C17—H17B	0.9600
C7—C12	1.398 (4)	C17—H17C	0.9600
C7—C14	1.487 (4)	C18—O3	1.427 (4)
C8—C9	1.385 (4)	C18—H18A	0.9600
C8—H8	0.9300	C18—H18B	0.9600
C9—C10	1.370 (4)	C18—H18C	0.9600
C9—H9	0.9300	C19—O4	1.429 (4)
C10—C11	1.379 (4)	C19—H19A	0.9600
C10—Cl1	1.745 (3)	C19—H19B	0.9600
C11—C12	1.382 (4)	C19—H19C	0.9600
C11—H11	0.9300

C6—C1—C2	120.9 (3)	C14—C13—H13	117.1
C6—C1—O5	119.2 (3)	O5—C13—H13	117.1
C2—C1—O5	119.9 (3)	C13—C14—C15	115.3 (3)
C3—C2—C1	118.7 (3)	C13—C14—C7	123.7 (3)
C3—C2—H2	120.7	C15—C14—C7	121.0 (2)
C1—C2—H2	120.7	O1—C15—O2	122.0 (3)
O4—C3—C2	124.2 (3)	O1—C15—C14	126.0 (3)
O4—C3—C4	114.6 (3)	O2—C15—C14	112.0 (2)
C2—C3—C4	121.2 (3)	O2—C16—C17	107.5 (3)
C5—C4—C3	118.5 (3)	O2—C16—H16A	110.2
C5—C4—H4	120.7	C17—C16—H16A	110.2
C3—C4—H4	120.7	O2—C16—H16B	110.2
O3—C5—C4	123.3 (3)	C17—C16—H16B	110.2
O3—C5—C6	115.7 (3)	H16A—C16—H16B	108.5
C4—C5—C6	121.0 (3)	C16—C17—H17A	109.5
C1—C6—C5	119.7 (3)	C16—C17—H17B	109.5
C1—C6—H6	120.2	H17A—C17—H17B	109.5
C5—C6—H6	120.2	C16—C17—H17C	109.5
C8—C7—C12	117.6 (3)	H17A—C17—H17C	109.5
C8—C7—C14	121.8 (3)	H17B—C17—H17C	109.5
C12—C7—C14	120.6 (3)	O3—C18—H18A	109.5
C9—C8—C7	121.7 (3)	O3—C18—H18B	109.5
C9—C8—H8	119.1	H18A—C18—H18B	109.5
C7—C8—H8	119.1	O3—C18—H18C	109.5
C10—C9—C8	118.9 (3)	H18A—C18—H18C	109.5
C10—C9—H9	120.5	H18B—C18—H18C	109.5
C8—C9—H9	120.5	O4—C19—H19A	109.5
C9—C10—C11	121.4 (3)	O4—C19—H19B	109.5
C9—C10—Cl1	119.6 (2)	H19A—C19—H19B	109.5
C11—C10—Cl1	119.1 (3)	O4—C19—H19C	109.5
C10—C11—C12	119.1 (3)	H19A—C19—H19C	109.5
C10—C11—H11	120.4	H19B—C19—H19C	109.5
C12—C11—H11	120.4	C13—O5—C1	123.7 (2)
C11—C12—C7	121.2 (3)	C15—O2—C16	117.4 (2)
C11—C12—H12	119.4	C5—O3—C18	117.4 (2)
C7—C12—H12	119.4	C3—O4—C19	116.9 (2)
C14—C13—O5	125.8 (3)

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉ClO₅
M_r	362.80
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.601 (2), 9.607 (3), 10.368 (2)
α, β, γ (°)	77.84 (2), 75.42 (3), 87.40 (3)
V (Å³)	904.7 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.932, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	6132, 3280, 2153
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.147, 1.03
No. of reflections	3280
No. of parameters	230
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.40

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the National Science & Technology Program of China (No. 2006BAC02A11), the Key Technologies R & D Program of the Education Commission of Hubei Province of China (No. Z20081701) and the Technologies R & D Program of Hubei Province of China (No. 2007AA301B62).

References

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