2-Chloro-phenyl 4-methyl-benzoate.

The conformation of the C=O bond in the title compound, C(14)H(11)ClO(2), is anti to the Cl atom, similar to what was observed in 2-methyl-phenyl 4-methyl-benzoate. The dihedral angle between the two aromatic rings is 59.36 (7)°.

Related literature

For related literature, see: Gowda et al. (2008a ▶,b ▶,c ▶); Nayak & Gowda (2008 ▶).

Experimental

Crystal data

C14H11ClO2

M = 246.68

Monoclinic,

a = 4.0538 (8) Å

b = 13.661 (3) Å

c = 10.975 (2) Å

β = 91.70 (2)°

V = 607.5 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.30 mm−1

T = 299 (2) K

0.48 × 0.24 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.869, T max = 0.954

4160 measured reflections

2238 independent reflections

1632 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.116

S = 1.15

2238 reflections

155 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.34 e Å−3

Absolute structure: Flack (1983 ▶), 957 Friedel pairs

Flack parameter: −0.09 (9)

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022290/bt2750sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022290/bt2750Isup2.hkl

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

C14H11ClO2	F000 = 256
Mr = 246.68	Dx = 1.349 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1136 reflections
a = 4.0538 (8) Å	θ = 2.4–27.8º
b = 13.661 (3) Å	µ = 0.30 mm−1
c = 10.975 (2) Å	T = 299 (2) K
β = 91.70 (2)º	Long needle, colourless
V = 607.5 (2) Å3	0.48 × 0.24 × 0.16 mm
Z = 2

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2238 independent reflections
Radiation source: fine-focus sealed tube	1632 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.012
T = 299(2) K	θmax = 26.4º
Rotation method data acquisition using ω and φ scans	θmin = 2.4º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)	h = −5→5
Tmin = 0.869, Tmax = 0.954	k = −17→15
4160 measured reflections	l = −13→7

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.035	w = 1/[σ2(Fo2) + (0.0644P)2 + 0.0085P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.116	(Δ/σ)max = 0.018
S = 1.15	Δρmax = 0.36 e Å−3
2238 reflections	Δρmin = −0.34 e Å−3
155 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 957 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.09 (9)
Secondary atom site location: difference Fourier map

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
C1	0.7402 (8)	0.6625 (2)	0.2945 (2)	0.0525 (7)
C2	0.5813 (7)	0.6919 (2)	0.3974 (2)	0.0570 (8)
C3	0.5373 (9)	0.7904 (3)	0.4209 (3)	0.0699 (10)
H3	0.4350	0.8104	0.4914	0.084*
C4	0.6454 (10)	0.8581 (3)	0.3396 (3)	0.0801 (11)
H4	0.6107	0.9243	0.3544	0.096*
C5	0.8047 (9)	0.8300 (3)	0.2364 (4)	0.0751 (10)
H5	0.8796	0.8765	0.1819	0.090*
C6	0.8512 (9)	0.7319 (3)	0.2154 (3)	0.0677 (8)
H6	0.9600	0.7122	0.1461	0.081*
C7	0.6657 (7)	0.5173 (2)	0.1796 (2)	0.0513 (7)
C8	0.7526 (7)	0.4132 (2)	0.1815 (2)	0.0460 (6)
C9	0.9317 (7)	0.3687 (2)	0.2745 (2)	0.0527 (7)
H9	1.0084	0.4057	0.3406	0.063*
C10	0.9986 (7)	0.2701 (2)	0.2709 (3)	0.0579 (7)
H10	1.1216	0.2417	0.3345	0.069*
C11	0.8878 (7)	0.2126 (2)	0.1756 (3)	0.0548 (7)
C12	0.7055 (7)	0.2569 (2)	0.0806 (2)	0.0562 (8)
H12	0.6276	0.2192	0.0153	0.067*
C13	0.6405 (7)	0.3554 (2)	0.0827 (2)	0.0552 (7)
H13	0.5216	0.3841	0.0184	0.066*
C14	0.9603 (8)	0.1054 (3)	0.1717 (3)	0.0726 (8)
H14A	1.1020	0.0880	0.2399	0.087*
H14B	1.0677	0.0900	0.0973	0.087*
H14C	0.7577	0.0693	0.1754	0.087*
O1	0.7986 (5)	0.56428 (14)	0.27927 (18)	0.0615 (6)
O2	0.4938 (7)	0.55841 (16)	0.1064 (2)	0.0776 (7)
Cl1	0.4406 (2)	0.60598 (9)	0.49831 (7)	0.0834 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0659 (17)	0.0460 (19)	0.0452 (14)	0.0061 (14)	−0.0050 (12)	−0.0011 (12)
C2	0.0682 (19)	0.055 (2)	0.0468 (15)	−0.0031 (15)	−0.0084 (13)	−0.0042 (13)
C3	0.088 (2)	0.067 (3)	0.0541 (17)	0.0134 (19)	−0.0046 (16)	−0.0151 (16)
C4	0.103 (3)	0.047 (2)	0.089 (2)	0.008 (2)	−0.022 (2)	−0.008 (2)
C5	0.092 (3)	0.050 (2)	0.082 (2)	−0.0120 (19)	−0.0133 (19)	0.0066 (17)
C6	0.083 (2)	0.061 (2)	0.0597 (16)	−0.0017 (17)	−0.0004 (15)	−0.0015 (15)
C7	0.0616 (17)	0.0522 (19)	0.0397 (12)	−0.0047 (14)	−0.0037 (12)	−0.0034 (13)
C8	0.0517 (15)	0.0460 (18)	0.0405 (12)	−0.0052 (12)	0.0039 (11)	−0.0023 (11)
C9	0.0592 (18)	0.054 (2)	0.0442 (12)	−0.0002 (14)	−0.0031 (12)	0.0047 (12)
C10	0.0649 (18)	0.055 (2)	0.0529 (15)	0.0061 (15)	−0.0060 (13)	0.0039 (13)
C11	0.0583 (15)	0.046 (2)	0.0602 (16)	−0.0030 (14)	0.0119 (13)	−0.0024 (12)
C12	0.0686 (18)	0.057 (2)	0.0431 (14)	−0.0091 (15)	0.0048 (13)	−0.0107 (13)
C13	0.0638 (18)	0.0587 (19)	0.0427 (12)	−0.0029 (16)	−0.0052 (12)	−0.0060 (14)
C14	0.080 (2)	0.054 (2)	0.084 (2)	0.000 (2)	0.0041 (16)	−0.0060 (19)
O1	0.0858 (15)	0.0461 (12)	0.0514 (11)	0.0094 (10)	−0.0167 (10)	−0.0022 (8)
O2	0.1052 (17)	0.0570 (14)	0.0686 (13)	0.0119 (13)	−0.0286 (13)	−0.0011 (11)
Cl1	0.1042 (7)	0.0856 (6)	0.0608 (4)	−0.0113 (6)	0.0082 (4)	0.0093 (4)

C1—C6	1.370 (5)	C8—C9	1.376 (4)
C1—O1	1.374 (3)	C8—C13	1.406 (4)
C1—C2	1.376 (4)	C9—C10	1.375 (4)
C2—C3	1.382 (4)	C9—H9	0.9300
C2—Cl1	1.723 (3)	C10—C11	1.373 (4)
C3—C4	1.366 (5)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.398 (4)
C4—C5	1.375 (6)	C11—C14	1.495 (5)
C4—H4	0.9300	C12—C13	1.372 (4)
C5—C6	1.373 (5)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—H14A	0.9600
C7—O2	1.188 (3)	C14—H14B	0.9600
C7—O1	1.365 (3)	C14—H14C	0.9600
C7—C8	1.465 (4)
C6—C1—O1	122.5 (3)	C13—C8—C7	117.5 (2)
C6—C1—C2	119.3 (3)	C10—C9—C8	120.8 (3)
O1—C1—C2	118.1 (3)	C10—C9—H9	119.6
C1—C2—C3	120.2 (3)	C8—C9—H9	119.6
C1—C2—Cl1	120.1 (2)	C11—C10—C9	121.5 (3)
C3—C2—Cl1	119.7 (2)	C11—C10—H10	119.3
C4—C3—C2	119.4 (3)	C9—C10—H10	119.3
C4—C3—H3	120.3	C10—C11—C12	118.3 (3)
C2—C3—H3	120.3	C10—C11—C14	121.5 (3)
C3—C4—C5	121.1 (4)	C12—C11—C14	120.2 (3)
C3—C4—H4	119.5	C13—C12—C11	120.6 (2)
C5—C4—H4	119.5	C13—C12—H12	119.7
C6—C5—C4	118.8 (4)	C11—C12—H12	119.7
C6—C5—H5	120.6	C12—C13—C8	120.4 (2)
C4—C5—H5	120.6	C12—C13—H13	119.8
C1—C6—C5	121.3 (3)	C8—C13—H13	119.8
C1—C6—H6	119.4	C11—C14—H14A	109.5
C5—C6—H6	119.4	C11—C14—H14B	109.5
O2—C7—O1	121.9 (3)	H14A—C14—H14B	109.5
O2—C7—C8	127.2 (2)	C11—C14—H14C	109.5
O1—C7—C8	110.8 (2)	H14A—C14—H14C	109.5
C9—C8—C13	118.3 (3)	H14B—C14—H14C	109.5
C9—C8—C7	124.1 (2)	C7—O1—C1	119.4 (2)
C6—C1—C2—C3	−0.6 (4)	C13—C8—C9—C10	−0.2 (4)
O1—C1—C2—C3	175.5 (3)	C7—C8—C9—C10	178.8 (3)
C6—C1—C2—Cl1	−179.8 (2)	C8—C9—C10—C11	−0.5 (4)
O1—C1—C2—Cl1	−3.7 (4)	C9—C10—C11—C12	0.5 (4)
C1—C2—C3—C4	1.7 (5)	C9—C10—C11—C14	−180.0 (3)
Cl1—C2—C3—C4	−179.1 (3)	C10—C11—C12—C13	0.2 (4)
C2—C3—C4—C5	−1.7 (5)	C14—C11—C12—C13	−179.3 (3)
C3—C4—C5—C6	0.6 (5)	C11—C12—C13—C8	−0.9 (4)
O1—C1—C6—C5	−176.4 (3)	C9—C8—C13—C12	0.9 (4)
C2—C1—C6—C5	−0.4 (5)	C7—C8—C13—C12	−178.2 (3)
C4—C5—C6—C1	0.4 (5)	O2—C7—O1—C1	−1.7 (4)
O2—C7—C8—C9	−174.5 (3)	C8—C7—O1—C1	−179.1 (3)
O1—C7—C8—C9	2.7 (4)	C6—C1—O1—C7	−64.4 (4)
O2—C7—C8—C13	4.5 (5)	C2—C1—O1—C7	119.6 (3)
O1—C7—C8—C13	−178.3 (2)