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

In the title compound, C(16)H(13)ClO(4), the two benzene rings make a dihedral angle of 86.38 (8)°. In the crystal, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules to form columns along the a axis. The mol-ecules are also stabilized by a π-π stacking inter-action, with a centroid-centroid distance of 3.7793 (10) Å between the inversion-related benzene rings.

Related literature

For general background to phenacyl benzoates, see: Rather & Reid (1919 ▶); Sheehan & Umezaw (1973 ▶); Ruzicka et al. (2002 ▶); Litera et al. (2006 ▶). For applications and synthesis of oxazoles, imidazoles and benzoxazepines, see: Huang et al. (1996 ▶); Gandhi et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H13ClO4

M = 304.71

Orthorhombic,

a = 7.7207 (6) Å

b = 14.4411 (12) Å

c = 26.064 (2) Å

V = 2906.0 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.28 mm−1

T = 296 K

0.51 × 0.29 × 0.19 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.829, T max = 0.950

16215 measured reflections

4027 independent reflections

2731 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.116

S = 1.02

4027 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.35 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/S1600536811021246/is2727sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021246/is2727Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811021246/is2727Isup3.cml

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

C16H13ClO4	F(000) = 1264
Mr = 304.71	Dx = 1.393 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3855 reflections
a = 7.7207 (6) Å	θ = 2.9–29.2°
b = 14.4411 (12) Å	µ = 0.28 mm−1
c = 26.064 (2) Å	T = 296 K
V = 2906.0 (4) Å3	Block, colourless
Z = 8	0.51 × 0.29 × 0.19 mm

Bruker APEXII DUO CCD area-detector diffractometer	4027 independent reflections
Radiation source: fine-focus sealed tube	2731 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 29.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→9
Tmin = 0.829, Tmax = 0.950	k = −14→20
16215 measured reflections	l = −36→35

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0471P)2 + 0.6504P] where P = (Fo2 + 2Fc2)/3
4027 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.35 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	1.18791 (7)	0.06652 (3)	1.10182 (2)	0.08142 (19)
O1	0.45975 (15)	0.12921 (11)	0.96747 (5)	0.0746 (4)
O2	0.49777 (16)	0.19520 (7)	0.87365 (5)	0.0624 (3)
O3	0.46624 (16)	0.04491 (8)	0.85569 (5)	0.0667 (3)
O4	0.19233 (15)	0.00492 (7)	0.79740 (4)	0.0600 (3)
C1	0.9263 (2)	0.14336 (11)	0.97782 (6)	0.0523 (4)
H1A	0.9515	0.1678	0.9457	0.063*
C2	1.0596 (2)	0.12582 (11)	1.01201 (7)	0.0571 (4)
H2A	1.1739	0.1382	1.0031	0.068*
C3	1.0198 (2)	0.08973 (10)	1.05937 (6)	0.0546 (4)
C4	0.8517 (2)	0.07047 (11)	1.07348 (7)	0.0582 (4)
H4A	0.8276	0.0459	1.1057	0.070*
C5	0.7198 (2)	0.08809 (11)	1.03928 (6)	0.0534 (4)
H5A	0.6059	0.0753	1.0485	0.064*
C6	0.75479 (19)	0.12480 (10)	0.99111 (6)	0.0455 (3)
C7	0.6086 (2)	0.14152 (10)	0.95508 (6)	0.0504 (4)
C8	0.6513 (2)	0.17422 (11)	0.90174 (6)	0.0543 (4)
H8A	0.7236	0.2290	0.9037	0.065*
H8B	0.7159	0.1265	0.8839	0.065*
C9	0.4084 (2)	0.12187 (10)	0.85521 (5)	0.0487 (3)
C10	0.2379 (2)	0.15154 (10)	0.83489 (5)	0.0462 (3)
C11	0.1787 (2)	0.24124 (11)	0.84420 (6)	0.0566 (4)
H11A	0.2469	0.2813	0.8635	0.068*
C12	0.0216 (3)	0.27210 (13)	0.82551 (7)	0.0672 (5)
H12A	−0.0156	0.3322	0.8321	0.081*
C13	−0.0790 (2)	0.21275 (13)	0.79706 (7)	0.0669 (5)
H13A	−0.1847	0.2331	0.7842	0.080*
C14	−0.0255 (2)	0.12352 (12)	0.78741 (6)	0.0594 (4)
H14A	−0.0954	0.0842	0.7682	0.071*
C15	0.1320 (2)	0.09184 (10)	0.80609 (5)	0.0475 (3)
C16	0.0868 (3)	−0.05690 (13)	0.76827 (8)	0.0822 (6)
H16A	0.1445	−0.1155	0.7650	0.123*
H16B	0.0669	−0.0313	0.7348	0.123*
H16C	−0.0221	−0.0655	0.7854	0.123*

	U11	U22	U33	U12	U13	U23
Cl1	0.0864 (4)	0.0640 (3)	0.0939 (4)	0.0087 (2)	−0.0384 (3)	−0.0086 (2)
O1	0.0402 (6)	0.1070 (11)	0.0766 (8)	−0.0079 (7)	0.0051 (6)	−0.0064 (7)
O2	0.0648 (7)	0.0453 (6)	0.0772 (8)	−0.0033 (5)	−0.0195 (6)	−0.0001 (5)
O3	0.0694 (8)	0.0505 (6)	0.0802 (8)	0.0105 (6)	−0.0215 (6)	−0.0133 (5)
O4	0.0707 (8)	0.0479 (6)	0.0615 (6)	0.0005 (5)	−0.0169 (5)	−0.0098 (5)
C1	0.0459 (8)	0.0574 (8)	0.0537 (8)	−0.0062 (7)	0.0056 (7)	−0.0057 (7)
C2	0.0407 (8)	0.0584 (9)	0.0721 (10)	−0.0042 (7)	0.0000 (7)	−0.0136 (8)
C3	0.0601 (10)	0.0413 (7)	0.0623 (9)	0.0040 (7)	−0.0108 (8)	−0.0124 (6)
C4	0.0712 (11)	0.0506 (8)	0.0529 (9)	−0.0036 (8)	0.0003 (8)	−0.0043 (7)
C5	0.0501 (9)	0.0535 (8)	0.0566 (9)	−0.0060 (7)	0.0095 (7)	−0.0071 (7)
C6	0.0412 (7)	0.0440 (7)	0.0513 (8)	−0.0034 (6)	0.0038 (6)	−0.0112 (6)
C7	0.0443 (8)	0.0480 (7)	0.0590 (9)	−0.0049 (7)	0.0024 (7)	−0.0121 (6)
C8	0.0497 (9)	0.0506 (8)	0.0626 (9)	−0.0059 (7)	−0.0071 (7)	−0.0005 (7)
C9	0.0575 (9)	0.0461 (8)	0.0426 (7)	−0.0003 (7)	−0.0033 (6)	−0.0024 (6)
C10	0.0542 (8)	0.0453 (7)	0.0390 (7)	0.0017 (6)	−0.0006 (6)	0.0012 (6)
C11	0.0667 (10)	0.0495 (8)	0.0535 (8)	0.0043 (8)	−0.0017 (7)	−0.0030 (7)
C12	0.0761 (12)	0.0580 (10)	0.0674 (10)	0.0192 (9)	0.0019 (9)	0.0036 (8)
C13	0.0600 (10)	0.0755 (11)	0.0653 (10)	0.0117 (9)	−0.0070 (9)	0.0138 (9)
C14	0.0608 (10)	0.0640 (10)	0.0532 (9)	−0.0026 (8)	−0.0110 (7)	0.0066 (7)
C15	0.0560 (9)	0.0487 (7)	0.0377 (7)	0.0005 (7)	−0.0012 (6)	0.0033 (6)
C16	0.1015 (16)	0.0592 (10)	0.0859 (13)	−0.0046 (11)	−0.0344 (12)	−0.0164 (9)

Cl1—C3	1.7380 (17)	C7—C8	1.505 (2)
O1—C7	1.2069 (19)	C8—H8A	0.9700
O2—C9	1.3521 (18)	C8—H8B	0.9700
O2—C8	1.426 (2)	C9—C10	1.482 (2)
O3—C9	1.1978 (18)	C10—C11	1.395 (2)
O4—C15	1.3579 (18)	C10—C15	1.406 (2)
O4—C16	1.428 (2)	C11—C12	1.381 (2)
C1—C2	1.384 (2)	C11—H11A	0.9300
C1—C6	1.395 (2)	C12—C13	1.374 (3)
C1—H1A	0.9300	C12—H12A	0.9300
C2—C3	1.375 (2)	C13—C14	1.376 (3)
C2—H2A	0.9300	C13—H13A	0.9300
C3—C4	1.377 (3)	C14—C15	1.388 (2)
C4—C5	1.377 (2)	C14—H14A	0.9300
C4—H4A	0.9300	C16—H16A	0.9600
C5—C6	1.390 (2)	C16—H16B	0.9600
C5—H5A	0.9300	C16—H16C	0.9600
C6—C7	1.488 (2)
C9—O2—C8	116.12 (12)	H8A—C8—H8B	108.0
C15—O4—C16	118.10 (13)	O3—C9—O2	122.20 (15)
C2—C1—C6	120.70 (15)	O3—C9—C10	127.08 (14)
C2—C1—H1A	119.6	O2—C9—C10	110.71 (12)
C6—C1—H1A	119.6	C11—C10—C15	118.16 (14)
C3—C2—C1	118.78 (15)	C11—C10—C9	119.82 (14)
C3—C2—H2A	120.6	C15—C10—C9	122.02 (13)
C1—C2—H2A	120.6	C12—C11—C10	121.74 (16)
C2—C3—C4	121.79 (15)	C12—C11—H11A	119.1
C2—C3—Cl1	118.55 (14)	C10—C11—H11A	119.1
C4—C3—Cl1	119.66 (14)	C13—C12—C11	119.05 (16)
C3—C4—C5	119.14 (16)	C13—C12—H12A	120.5
C3—C4—H4A	120.4	C11—C12—H12A	120.5
C5—C4—H4A	120.4	C12—C13—C14	120.86 (17)
C4—C5—C6	120.75 (15)	C12—C13—H13A	119.6
C4—C5—H5A	119.6	C14—C13—H13A	119.6
C6—C5—H5A	119.6	C13—C14—C15	120.51 (17)
C5—C6—C1	118.84 (15)	C13—C14—H14A	119.7
C5—C6—C7	118.98 (14)	C15—C14—H14A	119.7
C1—C6—C7	122.17 (14)	O4—C15—C14	123.15 (14)
O1—C7—C6	121.98 (15)	O4—C15—C10	117.17 (14)
O1—C7—C8	120.12 (15)	C14—C15—C10	119.67 (15)
C6—C7—C8	117.90 (13)	O4—C16—H16A	109.5
O2—C8—C7	111.06 (14)	O4—C16—H16B	109.5
O2—C8—H8A	109.4	H16A—C16—H16B	109.5
C7—C8—H8A	109.4	O4—C16—H16C	109.5
O2—C8—H8B	109.4	H16A—C16—H16C	109.5
C7—C8—H8B	109.4	H16B—C16—H16C	109.5
C6—C1—C2—C3	0.0 (2)	C8—O2—C9—C10	170.17 (13)
C1—C2—C3—C4	0.2 (2)	O3—C9—C10—C11	170.24 (16)
C1—C2—C3—Cl1	179.21 (12)	O2—C9—C10—C11	−10.50 (19)
C2—C3—C4—C5	−0.2 (2)	O3—C9—C10—C15	−9.9 (2)
Cl1—C3—C4—C5	−179.21 (12)	O2—C9—C10—C15	169.40 (13)
C3—C4—C5—C6	0.0 (2)	C15—C10—C11—C12	−0.7 (2)
C4—C5—C6—C1	0.2 (2)	C9—C10—C11—C12	179.24 (15)
C4—C5—C6—C7	179.14 (14)	C10—C11—C12—C13	0.1 (3)
C2—C1—C6—C5	−0.2 (2)	C11—C12—C13—C14	0.4 (3)
C2—C1—C6—C7	−179.12 (14)	C12—C13—C14—C15	−0.3 (3)
C5—C6—C7—O1	4.4 (2)	C16—O4—C15—C14	−1.0 (2)
C1—C6—C7—O1	−176.70 (15)	C16—O4—C15—C10	179.95 (16)
C5—C6—C7—C8	−175.29 (13)	C13—C14—C15—O4	−179.34 (15)
C1—C6—C7—C8	3.6 (2)	C13—C14—C15—C10	−0.3 (2)
C9—O2—C8—C7	−77.10 (17)	C11—C10—C15—O4	179.86 (13)
O1—C7—C8—O2	5.8 (2)	C9—C10—C15—O4	0.0 (2)
C6—C7—C8—O2	−174.59 (12)	C11—C10—C15—C14	0.7 (2)
C8—O2—C9—O3	−10.5 (2)	C9—C10—C15—C14	−179.15 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1i	0.93	2.40	3.301 (2)	164.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O1i	0.93	2.40	3.301 (2)	164

Symmetry code: (i) .