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

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

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.058
• wR factor = 0.147
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O5     --  C1      ..      10.06 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O5     --  C13     ..      11.51 su

Alert level C
            Value of measurement temperature given =   298.000
            Value of melting point given =     0.000
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O5
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

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

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

S2. Experimental

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.

S3. Refinement

All the H-atoms were placed in calculated positions and treated as rding atoms: C–H = 0.93–0.97 Å with U_iso(H) = 1.2U_eq(C) and 1.5U_eq(methyl C).

Computing details

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

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

Crystal data

C19H19ClO5	Z = 2
Mr = 362.80	F(000) = 382
Triclinic, P1	Dx = 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) Å^3

Data collection

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

Refinement

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

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)