2-(2,4-Dichloro-phen-yl)-2-oxoethyl 4-meth-oxy-benzoate.

In the title compound, C(16)H(12)Cl(2)O(4), the dihedral angle between the benzene rings is 70.11 (6)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds into a three-dimensional network. A C-H⋯π inter-action is also observed.

Related literature

For related structures and background to phenacyl benzoates, see: Fun et al. (2011a ▶,b ▶). For reference bond lengths, see: Allen et al. (1987 ▶). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H12Cl2O4

M = 339.16

Monoclinic,

a = 9.0508 (1) Å

b = 7.0846 (1) Å

c = 23.3337 (3) Å

β = 102.509 (1)°

V = 1460.67 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.46 mm−1

T = 100 K

0.36 × 0.30 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.852, T max = 0.942

24788 measured reflections

6502 independent reflections

5027 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.097

S = 1.02

6502 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811048720/hb6515sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048720/hb6515Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048720/hb6515Isup3.cml

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

C16H12Cl2O4	F(000) = 696
Mr = 339.16	Dx = 1.542 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6774 reflections
a = 9.0508 (1) Å	θ = 2.3–35.0°
b = 7.0846 (1) Å	µ = 0.46 mm−1
c = 23.3337 (3) Å	T = 100 K
β = 102.509 (1)°	Plate, colourless
V = 1460.67 (3) Å3	0.36 × 0.30 × 0.13 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	6502 independent reflections
Radiation source: fine-focus sealed tube	5027 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 35.2°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→12
Tmin = 0.852, Tmax = 0.942	k = −11→10
24788 measured reflections	l = −36→37

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.040P)2 + 0.5816P] where P = (Fo2 + 2Fc2)/3
6502 reflections	(Δ/σ)max = 0.004
200 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl1	0.66881 (3)	0.47740 (4)	1.178052 (11)	0.01926 (7)
Cl2	0.97532 (4)	1.12299 (5)	1.190485 (14)	0.02429 (7)
O1	0.65268 (10)	0.12541 (13)	1.01931 (3)	0.01802 (16)
O2	0.89431 (11)	0.33741 (15)	1.03290 (4)	0.0262 (2)
O3	0.56227 (12)	0.33618 (14)	0.94784 (4)	0.0265 (2)
O4	0.67141 (9)	−0.37683 (13)	0.79718 (3)	0.01786 (16)
C1	0.78521 (12)	0.62113 (17)	1.14699 (5)	0.01504 (19)
C2	0.82728 (12)	0.79099 (17)	1.17576 (5)	0.01596 (19)
H2A	0.7914	0.8237	1.2098	0.019*
C3	0.92243 (12)	0.91200 (17)	1.15397 (5)	0.0168 (2)
C4	0.97624 (13)	0.86750 (18)	1.10412 (5)	0.0186 (2)
H4A	1.0399	0.9525	1.0892	0.022*
C5	0.93461 (12)	0.69604 (18)	1.07679 (5)	0.0166 (2)
H5A	0.9726	0.6634	1.0432	0.020*
C6	0.83829 (12)	0.56876 (17)	1.09690 (4)	0.01481 (19)
C7	0.80621 (12)	0.38880 (18)	1.06248 (5)	0.0167 (2)
C8	0.66353 (13)	0.27437 (18)	1.06150 (5)	0.0177 (2)
H8A	0.6667	0.2205	1.1009	0.021*
H8B	0.5736	0.3572	1.0511	0.021*
C9	0.60826 (13)	0.17893 (18)	0.96250 (5)	0.0173 (2)
C10	0.62482 (12)	0.02595 (17)	0.92132 (4)	0.01478 (18)
C11	0.56119 (12)	0.05046 (17)	0.86144 (5)	0.01633 (19)
H11A	0.5058	0.1620	0.8484	0.020*
C12	0.57849 (12)	−0.08669 (18)	0.82128 (5)	0.0163 (2)
H12A	0.5342	−0.0699	0.7808	0.020*
C13	0.66111 (12)	−0.24992 (17)	0.84031 (5)	0.01497 (19)
C14	0.72520 (13)	−0.27659 (18)	0.89986 (5)	0.0168 (2)
H14A	0.7814	−0.3876	0.9129	0.020*
C15	0.70546 (13)	−0.13853 (17)	0.93974 (5)	0.0166 (2)
H15A	0.7477	−0.1566	0.9803	0.020*
C16	0.75581 (14)	−0.54602 (19)	0.81472 (5)	0.0216 (2)
H16A	0.7483	−0.6293	0.7807	0.032*
H16B	0.7147	−0.6104	0.8450	0.032*
H16C	0.8622	−0.5140	0.8305	0.032*

	U11	U22	U33	U12	U13	U23
Cl1	0.02234 (12)	0.01956 (14)	0.01897 (11)	−0.00520 (10)	0.01125 (9)	−0.00190 (10)
Cl2	0.02641 (14)	0.01913 (15)	0.02799 (14)	−0.00677 (11)	0.00735 (11)	−0.00626 (11)
O1	0.0223 (4)	0.0167 (4)	0.0153 (3)	−0.0022 (3)	0.0047 (3)	−0.0019 (3)
O2	0.0247 (4)	0.0287 (5)	0.0300 (4)	−0.0050 (4)	0.0162 (4)	−0.0101 (4)
O3	0.0382 (5)	0.0181 (5)	0.0227 (4)	0.0068 (4)	0.0051 (4)	−0.0010 (3)
O4	0.0203 (4)	0.0166 (4)	0.0168 (3)	0.0010 (3)	0.0041 (3)	−0.0025 (3)
C1	0.0136 (4)	0.0171 (5)	0.0151 (4)	−0.0018 (4)	0.0047 (3)	0.0008 (4)
C2	0.0160 (4)	0.0166 (5)	0.0154 (4)	−0.0001 (4)	0.0036 (3)	−0.0011 (4)
C3	0.0161 (4)	0.0151 (5)	0.0186 (4)	−0.0009 (4)	0.0026 (3)	−0.0003 (4)
C4	0.0182 (5)	0.0189 (6)	0.0194 (5)	−0.0026 (4)	0.0061 (4)	0.0017 (4)
C5	0.0156 (4)	0.0195 (6)	0.0157 (4)	−0.0005 (4)	0.0056 (3)	0.0011 (4)
C6	0.0138 (4)	0.0170 (5)	0.0139 (4)	−0.0008 (4)	0.0035 (3)	−0.0004 (4)
C7	0.0166 (4)	0.0190 (6)	0.0152 (4)	−0.0012 (4)	0.0051 (3)	−0.0008 (4)
C8	0.0196 (5)	0.0177 (6)	0.0170 (4)	−0.0037 (4)	0.0069 (4)	−0.0040 (4)
C9	0.0174 (5)	0.0179 (5)	0.0168 (4)	−0.0015 (4)	0.0044 (4)	−0.0012 (4)
C10	0.0152 (4)	0.0143 (5)	0.0151 (4)	−0.0022 (4)	0.0039 (3)	−0.0001 (4)
C11	0.0165 (4)	0.0161 (5)	0.0165 (4)	0.0008 (4)	0.0037 (3)	0.0018 (4)
C12	0.0163 (4)	0.0186 (6)	0.0139 (4)	0.0002 (4)	0.0028 (3)	0.0015 (4)
C13	0.0140 (4)	0.0158 (5)	0.0156 (4)	−0.0024 (4)	0.0041 (3)	−0.0001 (4)
C14	0.0181 (5)	0.0154 (5)	0.0164 (4)	0.0002 (4)	0.0027 (3)	0.0007 (4)
C15	0.0179 (5)	0.0174 (5)	0.0139 (4)	−0.0006 (4)	0.0021 (3)	0.0007 (4)
C16	0.0243 (5)	0.0167 (6)	0.0242 (5)	0.0015 (4)	0.0061 (4)	−0.0013 (4)

Cl1—C1	1.7329 (11)	C7—C8	1.5207 (16)
Cl2—C3	1.7357 (13)	C8—H8A	0.9900
O1—C9	1.3535 (14)	C8—H8B	0.9900
O1—C8	1.4320 (14)	C9—C10	1.4774 (16)
O2—C7	1.2178 (13)	C10—C15	1.3927 (16)
O3—C9	1.2123 (15)	C10—C11	1.4019 (15)
O4—C13	1.3677 (14)	C11—C12	1.3821 (16)
O4—C16	1.4326 (16)	C11—H11A	0.9500
C1—C2	1.3904 (16)	C12—C13	1.3963 (17)
C1—C6	1.4063 (14)	C12—H12A	0.9500
C2—C3	1.3874 (16)	C13—C14	1.3980 (15)
C2—H2A	0.9500	C14—C15	1.3878 (16)
C3—C4	1.3912 (16)	C14—H14A	0.9500
C4—C5	1.3857 (17)	C15—H15A	0.9500
C4—H4A	0.9500	C16—H16A	0.9800
C5—C6	1.4037 (16)	C16—H16B	0.9800
C5—H5A	0.9500	C16—H16C	0.9800
C6—C7	1.5013 (17)
C9—O1—C8	115.37 (10)	H8A—C8—H8B	108.2
C13—O4—C16	117.18 (9)	O3—C9—O1	123.00 (11)
C2—C1—C6	121.51 (10)	O3—C9—C10	124.59 (10)
C2—C1—Cl1	115.74 (8)	O1—C9—C10	112.40 (10)
C6—C1—Cl1	122.73 (9)	C15—C10—C11	119.07 (10)
C3—C2—C1	118.99 (10)	C15—C10—C9	122.23 (10)
C3—C2—H2A	120.5	C11—C10—C9	118.67 (10)
C1—C2—H2A	120.5	C12—C11—C10	120.42 (11)
C2—C3—C4	121.60 (11)	C12—C11—H11A	119.8
C2—C3—Cl2	118.64 (9)	C10—C11—H11A	119.8
C4—C3—Cl2	119.76 (9)	C11—C12—C13	119.88 (10)
C5—C4—C3	118.29 (11)	C11—C12—H12A	120.1
C5—C4—H4A	120.9	C13—C12—H12A	120.1
C3—C4—H4A	120.9	O4—C13—C12	115.32 (9)
C4—C5—C6	122.41 (10)	O4—C13—C14	124.26 (11)
C4—C5—H5A	118.8	C12—C13—C14	120.42 (10)
C6—C5—H5A	118.8	C15—C14—C13	119.03 (11)
C5—C6—C1	117.19 (11)	C15—C14—H14A	120.5
C5—C6—C7	115.39 (9)	C13—C14—H14A	120.5
C1—C6—C7	127.40 (10)	C14—C15—C10	121.18 (10)
O2—C7—C6	118.85 (10)	C14—C15—H15A	119.4
O2—C7—C8	119.36 (11)	C10—C15—H15A	119.4
C6—C7—C8	121.73 (9)	O4—C16—H16A	109.5
O1—C8—C7	109.56 (9)	O4—C16—H16B	109.5
O1—C8—H8A	109.8	H16A—C16—H16B	109.5
C7—C8—H8A	109.8	O4—C16—H16C	109.5
O1—C8—H8B	109.8	H16A—C16—H16C	109.5
C7—C8—H8B	109.8	H16B—C16—H16C	109.5
C6—C1—C2—C3	0.75 (17)	C6—C7—C8—O1	172.24 (10)
Cl1—C1—C2—C3	178.95 (9)	C8—O1—C9—O3	−8.97 (16)
C1—C2—C3—C4	0.12 (17)	C8—O1—C9—C10	170.10 (9)
C1—C2—C3—Cl2	−179.57 (9)	O3—C9—C10—C15	166.89 (12)
C2—C3—C4—C5	−1.14 (17)	O1—C9—C10—C15	−12.17 (15)
Cl2—C3—C4—C5	178.55 (9)	O3—C9—C10—C11	−10.99 (17)
C3—C4—C5—C6	1.34 (17)	O1—C9—C10—C11	169.95 (10)
C4—C5—C6—C1	−0.51 (17)	C15—C10—C11—C12	−0.08 (16)
C4—C5—C6—C7	−179.40 (11)	C9—C10—C11—C12	177.86 (10)
C2—C1—C6—C5	−0.56 (16)	C10—C11—C12—C13	−0.65 (17)
Cl1—C1—C6—C5	−178.63 (8)	C16—O4—C13—C12	179.72 (10)
C2—C1—C6—C7	178.18 (11)	C16—O4—C13—C14	−1.06 (16)
Cl1—C1—C6—C7	0.11 (17)	C11—C12—C13—O4	179.94 (10)
C5—C6—C7—O2	21.81 (16)	C11—C12—C13—C14	0.69 (17)
C1—C6—C7—O2	−156.95 (12)	O4—C13—C14—C15	−179.17 (10)
C5—C6—C7—C8	−155.42 (11)	C12—C13—C14—C15	0.00 (16)
C1—C6—C7—C8	25.83 (17)	C13—C14—C15—C10	−0.75 (17)
C9—O1—C8—C7	−75.93 (12)	C11—C10—C15—C14	0.79 (17)
O2—C7—C8—O1	−4.98 (16)	C9—C10—C15—C14	−177.08 (11)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O4i	0.95	2.54	3.4809 (13)	173
C5—H5A···O2ii	0.95	2.35	3.2745 (15)	164
C8—H8B···O3iii	0.99	2.50	3.4124 (17)	153
C16—H16C···Cg1iv	0.98	2.84	3.5655 (15)	132

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O4i	0.95	2.54	3.4809 (13)	173
C5—H5A⋯O2ii	0.95	2.35	3.2745 (15)	164
C8—H8B⋯O3iii	0.99	2.50	3.4124 (17)	153
C16—H16C⋯Cg1iv	0.98	2.84	3.5655 (15)	132

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