2-(4-Chloro-phen-yl)-2-oxoethyl 3,4-dimeth-oxy-benzoate.

In the title compound, C(17)H(15)ClO(5), the benzene rings forms a dihedral angle of 74.45 (10)°. In the crystal, mol-ecules are linked into C(13) chains along [011] via C-H⋯O hydrogen bonds. The crystal packing also features short Cl⋯Cl contacts of 3.1253 (10) Å.

Related literature

For a related structure and background to the properties and applications of phenacyl benzoate derivatives, see: Fun et al. (2011 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H15ClO5

M = 334.74

Triclinic,

a = 8.2277 (6) Å

b = 9.3380 (6) Å

c = 10.5986 (7) Å

α = 89.062 (2)°

β = 76.752 (2)°

γ = 83.674 (2)°

V = 787.76 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.27 mm−1

T = 296 K

0.31 × 0.22 × 0.13 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.922, T max = 0.966

12242 measured reflections

4535 independent reflections

3056 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.234

S = 1.05

4535 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.44 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/S1600536811048264/hb6500sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048264/hb6500Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048264/hb6500Isup3.cml

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

C17H15ClO5	Z = 2
Mr = 334.74	F(000) = 348
Triclinic, P1	Dx = 1.411 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2277 (6) Å	Cell parameters from 3650 reflections
b = 9.3380 (6) Å	θ = 2.6–29.9°
c = 10.5986 (7) Å	µ = 0.27 mm−1
α = 89.062 (2)°	T = 296 K
β = 76.752 (2)°	Needle, colourless
γ = 83.674 (2)°	0.31 × 0.22 × 0.13 mm
V = 787.76 (9) Å3

Bruker SMART APEXII DUO CCD diffractometer	4535 independent reflections
Radiation source: fine-focus sealed tube	3056 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 30.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.922, Tmax = 0.966	k = −13→11
12242 measured reflections	l = −14→14

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.234	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1525P)2 + 0.0576P] where P = (Fo2 + 2Fc2)/3
4535 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

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
Cl1	0.43412 (9)	0.12795 (7)	0.09809 (7)	0.0826 (3)
O1	0.2269 (3)	0.5869 (2)	0.59869 (14)	0.0726 (5)
O2	0.05337 (18)	0.83733 (16)	0.56180 (15)	0.0570 (4)
O3	0.31494 (19)	0.90247 (18)	0.50295 (14)	0.0618 (4)
O4	0.2833 (2)	1.30026 (19)	0.84644 (15)	0.0648 (5)
O5	−0.0100 (2)	1.30829 (18)	0.99126 (14)	0.0638 (4)
C1	0.1905 (3)	0.4855 (2)	0.27869 (18)	0.0484 (4)
H1A	0.1148	0.5615	0.2632	0.058*
C2	0.2470 (3)	0.3768 (2)	0.1871 (2)	0.0543 (5)
H2A	0.2108	0.3791	0.1101	0.065*
C3	0.3586 (3)	0.2648 (2)	0.2128 (2)	0.0530 (5)
C4	0.4143 (3)	0.2581 (3)	0.3249 (3)	0.0674 (6)
H4A	0.4896	0.1814	0.3397	0.081*
C5	0.3572 (3)	0.3669 (2)	0.4157 (2)	0.0593 (5)
H5A	0.3938	0.3631	0.4926	0.071*
C6	0.2449 (2)	0.48282 (19)	0.39351 (16)	0.0418 (4)
C7	0.1915 (2)	0.5993 (2)	0.49354 (17)	0.0467 (4)
C8	0.0964 (3)	0.7348 (2)	0.4583 (2)	0.0510 (5)
H8A	0.1644	0.7770	0.3828	0.061*
H8B	−0.0054	0.7113	0.4358	0.061*
C9	0.1789 (2)	0.9134 (2)	0.57600 (18)	0.0467 (4)
C10	0.1251 (2)	1.01115 (19)	0.69027 (17)	0.0443 (4)
C11	−0.0310 (3)	1.0126 (2)	0.7725 (2)	0.0510 (5)
H11A	−0.1037	0.9479	0.7590	0.061*
C12	−0.0813 (3)	1.1103 (2)	0.87599 (19)	0.0508 (5)
H12A	−0.1872	1.1106	0.9310	0.061*
C13	0.0261 (2)	1.2065 (2)	0.89671 (17)	0.0457 (4)
C14	0.1885 (2)	1.2027 (2)	0.81470 (17)	0.0449 (4)
C15	0.2367 (2)	1.1067 (2)	0.71224 (17)	0.0433 (4)
H15A	0.3430	1.1050	0.6576	0.052*
C16	0.4543 (3)	1.2941 (4)	0.7765 (2)	0.0756 (8)
H16A	0.5112	1.3597	0.8151	0.113*
H16B	0.4584	1.3204	0.6880	0.113*
H16C	0.5082	1.1979	0.7794	0.113*
C17	−0.1706 (3)	1.3195 (3)	1.0768 (2)	0.0704 (7)
H17A	−0.1783	1.3946	1.1394	0.106*
H17B	−0.1871	1.2296	1.1207	0.106*
H17C	−0.2554	1.3418	1.0284	0.106*

	U11	U22	U33	U12	U13	U23
Cl1	0.0809 (5)	0.0657 (4)	0.0905 (5)	−0.0085 (3)	0.0055 (3)	−0.0403 (3)
O1	0.0967 (13)	0.0770 (11)	0.0437 (8)	0.0070 (9)	−0.0223 (8)	−0.0125 (7)
O2	0.0492 (8)	0.0534 (8)	0.0659 (9)	−0.0067 (6)	−0.0058 (6)	−0.0238 (7)
O3	0.0507 (8)	0.0716 (10)	0.0580 (8)	−0.0082 (7)	0.0002 (6)	−0.0221 (7)
O4	0.0603 (9)	0.0731 (10)	0.0626 (9)	−0.0264 (8)	−0.0069 (7)	−0.0200 (8)
O5	0.0633 (9)	0.0717 (10)	0.0532 (8)	−0.0114 (7)	−0.0028 (7)	−0.0268 (7)
C1	0.0541 (11)	0.0444 (9)	0.0500 (10)	−0.0020 (7)	−0.0197 (8)	−0.0070 (7)
C2	0.0626 (12)	0.0537 (11)	0.0502 (10)	−0.0094 (9)	−0.0176 (9)	−0.0120 (8)
C3	0.0481 (10)	0.0473 (10)	0.0599 (11)	−0.0090 (8)	−0.0021 (8)	−0.0159 (8)
C4	0.0667 (14)	0.0561 (12)	0.0789 (15)	0.0152 (10)	−0.0252 (12)	−0.0127 (11)
C5	0.0662 (13)	0.0572 (12)	0.0579 (11)	0.0074 (10)	−0.0273 (10)	−0.0083 (9)
C6	0.0432 (9)	0.0416 (9)	0.0418 (8)	−0.0070 (7)	−0.0106 (7)	−0.0033 (7)
C7	0.0491 (10)	0.0497 (10)	0.0411 (8)	−0.0078 (8)	−0.0081 (7)	−0.0074 (7)
C8	0.0501 (10)	0.0487 (10)	0.0545 (10)	−0.0020 (8)	−0.0133 (8)	−0.0156 (8)
C9	0.0438 (9)	0.0447 (9)	0.0496 (9)	−0.0032 (7)	−0.0069 (7)	−0.0080 (7)
C10	0.0456 (9)	0.0411 (9)	0.0446 (9)	−0.0032 (7)	−0.0069 (7)	−0.0079 (7)
C11	0.0482 (10)	0.0498 (10)	0.0532 (10)	−0.0107 (8)	−0.0048 (8)	−0.0099 (8)
C12	0.0463 (10)	0.0543 (11)	0.0474 (9)	−0.0078 (8)	0.0002 (8)	−0.0091 (8)
C13	0.0518 (10)	0.0455 (9)	0.0388 (8)	−0.0035 (7)	−0.0088 (7)	−0.0062 (7)
C14	0.0476 (9)	0.0455 (9)	0.0437 (9)	−0.0094 (7)	−0.0123 (7)	−0.0031 (7)
C15	0.0408 (9)	0.0452 (9)	0.0424 (8)	−0.0048 (7)	−0.0061 (7)	−0.0021 (7)
C16	0.0647 (14)	0.107 (2)	0.0586 (12)	−0.0436 (14)	−0.0054 (10)	−0.0113 (13)
C17	0.0721 (15)	0.0784 (16)	0.0519 (12)	0.0014 (12)	0.0013 (10)	−0.0237 (11)

Cl1—C3	1.739 (2)	C7—C8	1.502 (3)
O1—C7	1.215 (2)	C8—H8A	0.9700
O2—C9	1.353 (2)	C8—H8B	0.9700
O2—C8	1.423 (2)	C9—C10	1.482 (2)
O3—C9	1.201 (2)	C10—C11	1.376 (3)
O4—C14	1.356 (2)	C10—C15	1.407 (2)
O4—C16	1.427 (3)	C11—C12	1.396 (3)
O5—C13	1.352 (2)	C11—H11A	0.9300
O5—C17	1.415 (3)	C12—C13	1.381 (3)
C1—C2	1.382 (3)	C12—H12A	0.9300
C1—C6	1.389 (3)	C13—C14	1.414 (3)
C1—H1A	0.9300	C14—C15	1.377 (2)
C2—C3	1.380 (3)	C15—H15A	0.9300
C2—H2A	0.9300	C16—H16A	0.9600
C3—C4	1.367 (3)	C16—H16B	0.9600
C4—C5	1.378 (3)	C16—H16C	0.9600
C4—H4A	0.9300	C17—H17A	0.9600
C5—C6	1.397 (3)	C17—H17B	0.9600
C5—H5A	0.9300	C17—H17C	0.9600
C6—C7	1.489 (2)
C9—O2—C8	115.33 (15)	O2—C9—C10	111.37 (16)
C14—O4—C16	117.59 (17)	C11—C10—C15	119.80 (16)
C13—O5—C17	118.36 (17)	C11—C10—C9	121.82 (16)
C2—C1—C6	121.01 (18)	C15—C10—C9	118.36 (16)
C2—C1—H1A	119.5	C10—C11—C12	120.61 (17)
C6—C1—H1A	119.5	C10—C11—H11A	119.7
C3—C2—C1	118.36 (18)	C12—C11—H11A	119.7
C3—C2—H2A	120.8	C13—C12—C11	119.99 (17)
C1—C2—H2A	120.8	C13—C12—H12A	120.0
C4—C3—C2	122.28 (19)	C11—C12—H12A	120.0
C4—C3—Cl1	118.43 (18)	O5—C13—C12	125.37 (18)
C2—C3—Cl1	119.28 (17)	O5—C13—C14	115.02 (16)
C3—C4—C5	119.0 (2)	C12—C13—C14	119.61 (16)
C3—C4—H4A	120.5	O4—C14—C15	125.87 (17)
C5—C4—H4A	120.5	O4—C14—C13	114.09 (16)
C4—C5—C6	120.66 (19)	C15—C14—C13	120.04 (16)
C4—C5—H5A	119.7	C14—C15—C10	119.91 (16)
C6—C5—H5A	119.7	C14—C15—H15A	120.0
C1—C6—C5	118.69 (18)	C10—C15—H15A	120.0
C1—C6—C7	123.08 (17)	O4—C16—H16A	109.5
C5—C6—C7	118.22 (16)	O4—C16—H16B	109.5
O1—C7—C6	121.47 (18)	H16A—C16—H16B	109.5
O1—C7—C8	121.02 (18)	O4—C16—H16C	109.5
C6—C7—C8	117.49 (15)	H16A—C16—H16C	109.5
O2—C8—C7	111.92 (16)	H16B—C16—H16C	109.5
O2—C8—H8A	109.2	O5—C17—H17A	109.5
C7—C8—H8A	109.2	O5—C17—H17B	109.5
O2—C8—H8B	109.2	H17A—C17—H17B	109.5
C7—C8—H8B	109.2	O5—C17—H17C	109.5
H8A—C8—H8B	107.9	H17A—C17—H17C	109.5
O3—C9—O2	123.14 (17)	H17B—C17—H17C	109.5
O3—C9—C10	125.48 (17)
C6—C1—C2—C3	0.3 (3)	O2—C9—C10—C11	3.8 (3)
C1—C2—C3—C4	0.0 (3)	O3—C9—C10—C15	4.4 (3)
C1—C2—C3—Cl1	−179.06 (15)	O2—C9—C10—C15	−174.77 (16)
C2—C3—C4—C5	0.0 (4)	C15—C10—C11—C12	1.5 (3)
Cl1—C3—C4—C5	179.11 (19)	C9—C10—C11—C12	−177.06 (18)
C3—C4—C5—C6	−0.4 (4)	C10—C11—C12—C13	−0.1 (3)
C2—C1—C6—C5	−0.7 (3)	C17—O5—C13—C12	−0.3 (3)
C2—C1—C6—C7	178.23 (17)	C17—O5—C13—C14	179.6 (2)
C4—C5—C6—C1	0.7 (3)	C11—C12—C13—O5	178.19 (19)
C4—C5—C6—C7	−178.2 (2)	C11—C12—C13—C14	−1.7 (3)
C1—C6—C7—O1	172.1 (2)	C16—O4—C14—C15	−6.9 (3)
C5—C6—C7—O1	−8.9 (3)	C16—O4—C14—C13	174.0 (2)
C1—C6—C7—C8	−9.6 (3)	O5—C13—C14—O4	1.4 (3)
C5—C6—C7—C8	169.30 (19)	C12—C13—C14—O4	−178.68 (19)
C9—O2—C8—C7	79.1 (2)	O5—C13—C14—C15	−177.72 (17)
O1—C7—C8—O2	−1.5 (3)	C12—C13—C14—C15	2.2 (3)
C6—C7—C8—O2	−179.80 (15)	O4—C14—C15—C10	−179.87 (18)
C8—O2—C9—O3	4.0 (3)	C13—C14—C15—C10	−0.8 (3)
C8—O2—C9—C10	−176.80 (16)	C11—C10—C15—C14	−1.0 (3)
O3—C9—C10—C11	−177.1 (2)	C9—C10—C15—C14	177.60 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O5i	0.93	2.58	3.397 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O5i	0.93	2.58	3.397 (3)	147

Symmetry code: (i) .