Ethyl 2-[4-(4-chloro-benzo-yl)phen-oxy]-2-methyl-propano-ate.

In the title compound, C(19)H(19)ClO(4), the dihedral angle between the mean planes of the benzene rings is 126.8 (1)°. Weak C-H⋯O inter-actions are observed.

Related literature

For background, see: Guichard et al. (2000 ▶). For the synthesis of the title compound, see: Bandgar et al., (2011 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H19ClO4

M = 346.79

Orthorhombic,

a = 13.677 (3) Å

b = 16.420 (3) Å

c = 7.9490 (16) Å

V = 1785.2 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 293 K

0.20 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.955, T max = 0.977

3465 measured reflections

3459 independent reflections

1971 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.180

S = 1.00

3459 reflections

218 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), with 1692 Friedel pairs

Flack parameter: 0.04 (17)

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812021149/jj2137sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021149/jj2137Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021149/jj2137Isup3.cml

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

C19H19ClO4	F(000) = 728
Mr = 346.79	Dx = 1.290 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 25 reflections
a = 13.677 (3) Å	θ = 9–12°
b = 16.420 (3) Å	µ = 0.23 mm−1
c = 7.9490 (16) Å	T = 293 K
V = 1785.2 (6) Å3	Block, colourless
Z = 4	0.20 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	3459 independent reflections
Radiation source: fine-focus sealed tube	1971 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
Detector resolution: 16.0355 pixels mm-1	θmax = 25.4°, θmin = 2.5°
ω/2θ scans	h = 0→16
Absorption correction: ψ scan (North et al., 1968)	k = −19→19
Tmin = 0.955, Tmax = 0.977	l = 0→9
3465 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.068	w = 1/[σ2(Fo2) + (0.078P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.180	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.21 e Å−3
3459 reflections	Δρmin = −0.21 e Å−3
218 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.029 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 1692 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.04 (17)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl	0.48890 (13)	0.70175 (10)	0.0275 (3)	0.1012 (7)
O1	0.5732 (3)	0.8850 (3)	0.7608 (6)	0.0837 (13)
C1	0.4206 (4)	0.8448 (3)	0.4133 (8)	0.0591 (15)
H1A	0.3735	0.8840	0.4365	0.071*
O2	0.1445 (2)	0.96725 (19)	1.0184 (5)	0.0586 (10)
C2	0.4204 (4)	0.8080 (3)	0.2568 (8)	0.0679 (17)
H2A	0.3747	0.8228	0.1757	0.081*
O3	0.2113 (3)	0.9435 (2)	1.3404 (6)	0.0726 (13)
C3	0.4895 (4)	0.7489 (3)	0.2235 (9)	0.0654 (17)
O4	0.2075 (3)	1.0773 (2)	1.3897 (5)	0.0620 (11)
C4	0.5574 (4)	0.7267 (3)	0.3426 (9)	0.0690 (19)
H4A	0.6030	0.6861	0.3196	0.083*
C5	0.5571 (4)	0.7653 (3)	0.4965 (9)	0.0629 (16)
H5A	0.6041	0.7510	0.5757	0.075*
C6	0.4886 (3)	0.8254 (3)	0.5378 (9)	0.0513 (13)
C7	0.4929 (3)	0.8691 (3)	0.7002 (7)	0.0536 (14)
C8	0.4017 (4)	0.8941 (3)	0.7865 (7)	0.0520 (14)
C9	0.4053 (4)	0.9562 (3)	0.9038 (8)	0.0574 (15)
H9A	0.4650	0.9809	0.9267	0.069*
C10	0.3229 (4)	0.9827 (3)	0.9882 (7)	0.0573 (14)
H10A	0.3272	1.0245	1.0668	0.069*
C11	0.2338 (4)	0.9463 (3)	0.9542 (7)	0.0479 (13)
C12	0.2301 (4)	0.8814 (3)	0.8440 (7)	0.0541 (14)
H12A	0.1711	0.8545	0.8270	0.065*
C13	0.3114 (4)	0.8558 (3)	0.7596 (8)	0.0580 (15)
H13A	0.3069	0.8128	0.6839	0.070*
C14	0.1328 (4)	1.0324 (3)	1.1404 (7)	0.0509 (13)
C15	0.1562 (4)	1.1156 (3)	1.0644 (7)	0.0706 (17)
H15A	0.2247	1.1185	1.0390	0.106*
H15B	0.1395	1.1575	1.1434	0.106*
H15C	0.1191	1.1229	0.9630	0.106*
C16	0.0242 (4)	1.0277 (3)	1.1840 (8)	0.0731 (18)
H16A	0.0101	0.9757	1.2338	0.110*
H16B	−0.0139	1.0342	1.0834	0.110*
H16C	0.0081	1.0702	1.2621	0.110*
C17	0.1892 (3)	1.0110 (3)	1.3001 (7)	0.0512 (13)
C18	0.2573 (5)	1.0655 (4)	1.5498 (9)	0.0796 (19)
H18A	0.3151	1.0322	1.5333	0.096*
H18B	0.2144	1.0374	1.6278	0.096*
C19	0.2854 (5)	1.1450 (4)	1.6197 (10)	0.098 (2)
H19A	0.3193	1.1372	1.7241	0.148*
H19B	0.2278	1.1771	1.6389	0.148*
H19C	0.3274	1.1727	1.5416	0.148*

	U11	U22	U33	U12	U13	U23
Cl	0.1114 (14)	0.0824 (11)	0.1098 (14)	0.0005 (9)	0.0354 (14)	−0.0362 (12)
O1	0.045 (2)	0.118 (3)	0.088 (3)	−0.003 (2)	−0.003 (2)	−0.001 (3)
C1	0.054 (3)	0.048 (3)	0.075 (4)	0.009 (3)	0.010 (3)	−0.003 (3)
O2	0.045 (2)	0.072 (2)	0.059 (2)	0.0055 (16)	−0.002 (2)	−0.022 (2)
C2	0.073 (4)	0.055 (3)	0.076 (4)	0.008 (3)	0.015 (4)	−0.004 (3)
O3	0.084 (3)	0.049 (2)	0.085 (3)	0.002 (2)	−0.023 (2)	0.003 (2)
C3	0.059 (4)	0.053 (3)	0.084 (4)	0.000 (3)	0.025 (4)	−0.004 (3)
O4	0.073 (3)	0.060 (2)	0.053 (2)	0.002 (2)	−0.013 (2)	−0.009 (2)
C4	0.052 (3)	0.049 (3)	0.106 (6)	0.007 (3)	0.034 (4)	0.005 (4)
C5	0.049 (3)	0.057 (3)	0.082 (5)	0.013 (3)	0.018 (4)	0.020 (4)
C6	0.038 (3)	0.048 (3)	0.068 (4)	0.001 (2)	0.014 (3)	0.015 (3)
C7	0.040 (3)	0.060 (3)	0.061 (4)	0.003 (2)	0.003 (3)	0.012 (3)
C8	0.045 (3)	0.052 (3)	0.059 (4)	0.002 (2)	−0.002 (3)	0.000 (3)
C9	0.040 (3)	0.068 (3)	0.064 (4)	−0.009 (3)	−0.006 (3)	0.007 (3)
C10	0.055 (3)	0.062 (3)	0.055 (4)	−0.007 (3)	−0.003 (3)	−0.012 (3)
C11	0.044 (3)	0.055 (3)	0.044 (3)	−0.001 (2)	−0.001 (3)	0.000 (3)
C12	0.041 (3)	0.057 (3)	0.065 (4)	−0.007 (2)	0.003 (3)	−0.020 (3)
C13	0.052 (3)	0.056 (3)	0.066 (4)	−0.007 (2)	0.002 (3)	−0.019 (3)
C14	0.049 (3)	0.055 (3)	0.048 (3)	0.001 (2)	−0.003 (3)	−0.008 (3)
C15	0.084 (4)	0.065 (3)	0.063 (4)	0.015 (3)	−0.010 (3)	0.007 (3)
C16	0.054 (4)	0.085 (4)	0.080 (5)	0.012 (3)	0.000 (3)	−0.027 (4)
C17	0.048 (3)	0.057 (3)	0.048 (3)	0.000 (3)	−0.002 (3)	−0.011 (3)
C18	0.103 (5)	0.078 (4)	0.058 (4)	−0.012 (4)	−0.029 (4)	0.004 (4)
C19	0.105 (5)	0.103 (5)	0.088 (5)	−0.029 (4)	−0.012 (5)	−0.024 (5)

Cl—C3	1.740 (7)	C9—H9A	0.9300
O1—C7	1.227 (6)	C10—C11	1.383 (7)
C1—C2	1.383 (8)	C10—H10A	0.9300
C1—C6	1.395 (7)	C11—C12	1.380 (7)
C1—H1A	0.9300	C12—C13	1.365 (7)
O2—C11	1.369 (6)	C12—H12A	0.9300
O2—C14	1.452 (6)	C13—H13A	0.9300
C2—C3	1.380 (7)	C14—C17	1.527 (7)
C2—H2A	0.9300	C14—C15	1.527 (7)
O3—C17	1.192 (6)	C14—C16	1.527 (7)
C3—C4	1.376 (8)	C15—H15A	0.9600
O4—C17	1.325 (6)	C15—H15B	0.9600
O4—C18	1.457 (7)	C15—H15C	0.9600
C4—C5	1.378 (8)	C16—H16A	0.9600
C4—H4A	0.9300	C16—H16B	0.9600
C5—C6	1.399 (7)	C16—H16C	0.9600
C5—H5A	0.9300	C18—C19	1.470 (7)
C6—C7	1.478 (8)	C18—H18A	0.9700
C7—C8	1.482 (7)	C18—H18B	0.9700
C8—C9	1.382 (7)	C19—H19A	0.9600
C8—C13	1.401 (7)	C19—H19B	0.9600
C9—C10	1.382 (7)	C19—H19C	0.9600
C2—C1—C6	122.7 (5)	C11—C12—H12A	119.4
C2—C1—H1A	118.7	C12—C13—C8	120.3 (5)
C6—C1—H1A	118.7	C12—C13—H13A	119.8
C11—O2—C14	122.2 (4)	C8—C13—H13A	119.8
C3—C2—C1	118.5 (6)	O2—C14—C17	109.3 (4)
C3—C2—H2A	120.7	O2—C14—C15	111.8 (5)
C1—C2—H2A	120.7	C17—C14—C15	115.4 (4)
C4—C3—C2	121.2 (6)	O2—C14—C16	102.8 (4)
C4—C3—Cl	120.1 (4)	C17—C14—C16	106.9 (5)
C2—C3—Cl	118.8 (5)	C15—C14—C16	109.8 (4)
C17—O4—C18	116.6 (4)	C14—C15—H15A	109.5
C3—C4—C5	119.1 (5)	C14—C15—H15B	109.5
C3—C4—H4A	120.5	H15A—C15—H15B	109.5
C5—C4—H4A	120.5	C14—C15—H15C	109.5
C4—C5—C6	122.4 (6)	H15A—C15—H15C	109.5
C4—C5—H5A	118.8	H15B—C15—H15C	109.5
C6—C5—H5A	118.8	C14—C16—H16A	109.5
C1—C6—C5	116.2 (6)	C14—C16—H16B	109.5
C1—C6—C7	122.4 (4)	H16A—C16—H16B	109.5
C5—C6—C7	121.4 (5)	C14—C16—H16C	109.5
O1—C7—C6	118.8 (5)	H16A—C16—H16C	109.5
O1—C7—C8	120.8 (5)	H16B—C16—H16C	109.5
C6—C7—C8	120.3 (5)	O3—C17—O4	124.9 (5)
C9—C8—C13	117.7 (5)	O3—C17—C14	124.4 (5)
C9—C8—C7	119.1 (5)	O4—C17—C14	110.7 (4)
C13—C8—C7	123.1 (5)	O4—C18—C19	109.5 (5)
C10—C9—C8	122.0 (5)	O4—C18—H18A	109.8
C10—C9—H9A	119.0	C19—C18—H18A	109.8
C8—C9—H9A	119.0	O4—C18—H18B	109.8
C9—C10—C11	119.2 (5)	C19—C18—H18B	109.8
C9—C10—H10A	120.4	H18A—C18—H18B	108.2
C11—C10—H10A	120.4	C18—C19—H19A	109.5
O2—C11—C12	113.4 (4)	C18—C19—H19B	109.5
O2—C11—C10	127.2 (5)	H19A—C19—H19B	109.5
C12—C11—C10	119.3 (5)	C18—C19—H19C	109.5
C13—C12—C11	121.3 (5)	H19A—C19—H19C	109.5
C13—C12—H12A	119.4	H19B—C19—H19C	109.5
C6—C1—C2—C3	0.9 (8)	C14—O2—C11—C12	178.2 (5)
C1—C2—C3—C4	0.0 (8)	C14—O2—C11—C10	−1.9 (8)
C1—C2—C3—Cl	179.4 (4)	C9—C10—C11—O2	−176.3 (5)
C2—C3—C4—C5	−1.2 (8)	C9—C10—C11—C12	3.6 (8)
Cl—C3—C4—C5	179.5 (4)	O2—C11—C12—C13	175.6 (5)
C3—C4—C5—C6	1.5 (8)	C10—C11—C12—C13	−4.4 (8)
C2—C1—C6—C5	−0.6 (7)	C11—C12—C13—C8	1.6 (9)
C2—C1—C6—C7	175.4 (5)	C9—C8—C13—C12	1.8 (8)
C4—C5—C6—C1	−0.6 (7)	C7—C8—C13—C12	179.5 (5)
C4—C5—C6—C7	−176.7 (5)	C11—O2—C14—C17	−62.1 (6)
C1—C6—C7—O1	−140.2 (5)	C11—O2—C14—C15	66.9 (6)
C5—C6—C7—O1	35.6 (7)	C11—O2—C14—C16	−175.4 (5)
C1—C6—C7—C8	39.0 (7)	C18—O4—C17—O3	−0.7 (8)
C5—C6—C7—C8	−145.2 (5)	C18—O4—C17—C14	177.4 (5)
O1—C7—C8—C9	20.4 (7)	O2—C14—C17—O3	−22.5 (7)
C6—C7—C8—C9	−158.8 (5)	C15—C14—C17—O3	−149.5 (5)
O1—C7—C8—C13	−157.2 (5)	C16—C14—C17—O3	88.1 (6)
C6—C7—C8—C13	23.5 (7)	O2—C14—C17—O4	159.4 (4)
C13—C8—C9—C10	−2.5 (8)	C15—C14—C17—O4	32.4 (6)
C7—C8—C9—C10	179.7 (5)	C16—C14—C17—O4	−90.0 (5)
C8—C9—C10—C11	−0.2 (8)	C17—O4—C18—C19	171.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O3i	0.93	2.54	3.340 (7)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O3i	0.93	2.54	3.340 (7)	144

Symmetry code: (i) .