4-Chloro-phenyl 4-methyl-benzoate.

The crystal structure of the title compound (4CP4MBA), C(14)H(11)ClO(2), resembles those of 3-chloro-phenyl 4-methyl-benzoate (3CP4MBA), 4-methyl-phenyl 4-methyl-benzoate (4MP4MBA), 4-methyl-phenyl 4-chloro-benzoate (4MP4CBA) and other aryl benzoates with similar bond parameters. The dihedral angle between the benzene rings in 4CP4MBA is 63.89 (8)°, compared with 71.75 (7)° in 3CP4MBA, 63.57 (5)° in 4MP4MBA and 51.86 (4)° in 4MP4CBA. In the crystal structure of the title compound, the mol-ecules are linked into an infinite chain along the a axis via C-H-O hydrogen bonds.

Related literature

For related literature, see: Gowda et al. (2007 ▶); Gowda, Foro, et al. (2008 ▶); Gowda, Svoboda et al. (2008 ▶); Nayak & Gowda (2008 ▶).

Experimental

Crystal data

C14H11ClO2

M = 246.68

Monoclinic,

a = 6.048 (2) Å

b = 7.559 (2) Å

c = 26.487 (5) Å

β = 95.68 (4)°

V = 1205.0 (6) Å3

Z = 4

Cu Kα radiation

μ = 2.69 mm−1

T = 299 (2) K

0.65 × 0.60 × 0.45 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.216, T max = 0.298

2872 measured reflections

2141 independent reflections

1968 reflections with I > 2σ(I)

R int = 0.053

3 standard reflections frequency: 120 min intensity decay: 1.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.092

wR(F 2) = 0.313

S = 1.51

2141 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.94 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); 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/S1600536808021697/is2314sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021697/is2314Isup2.hkl

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

C14H11ClO2	F000 = 512
Mr = 246.68	Dx = 1.360 Mg m−3
Monoclinic, P21/n	Cu Kα radiation λ = 1.54180 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 6.048 (2) Å	θ = 3.4–16.9º
b = 7.559 (2) Å	µ = 2.69 mm−1
c = 26.487 (5) Å	T = 299 (2) K
β = 95.68 (4)º	Prism, colourless
V = 1205.0 (6) Å3	0.65 × 0.60 × 0.45 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.053
Radiation source: fine-focus sealed tube	θmax = 67.0º
Monochromator: graphite	θmin = 3.4º
T = 299(2) K	h = −7→2
ω/2θ scans	k = −9→0
Absorption correction: ψ scan(North et al., 1968)	l = −31→31
Tmin = 0.216, Tmax = 0.298	3 standard reflections
2872 measured reflections	every 120 min
2141 independent reflections	intensity decay: 1.5%
1968 reflections with I > 2σ(I)

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.092	w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.313	(Δ/σ)max = 0.001
S = 1.51	Δρmax = 0.53 e Å−3
2141 reflections	Δρmin = −0.94 e Å−3
156 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.048 (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
Cl1	0.75384 (13)	0.28660 (13)	0.53235 (3)	0.0895 (6)
O1	0.2922 (3)	0.3273 (3)	0.32780 (7)	0.0708 (7)
O2	0.0565 (3)	0.5372 (3)	0.34855 (6)	0.0655 (7)
C1	0.3932 (4)	0.3235 (3)	0.37781 (9)	0.0577 (7)
C2	0.5981 (4)	0.4028 (4)	0.38707 (10)	0.0627 (8)
H2	0.6612	0.4629	0.3614	0.075*
C3	0.7081 (4)	0.3910 (3)	0.43527 (11)	0.0643 (8)
H3	0.8467	0.4436	0.4425	0.077*
C4	0.6124 (5)	0.3022 (3)	0.47205 (10)	0.0618 (8)
C5	0.4096 (5)	0.2231 (4)	0.46293 (11)	0.0697 (8)
H5	0.3473	0.1627	0.4886	0.084*
C6	0.2981 (4)	0.2344 (4)	0.41478 (11)	0.0693 (8)
H6	0.1596	0.1815	0.4078	0.083*
C7	0.1213 (3)	0.4406 (3)	0.31755 (8)	0.0522 (7)
C8	0.0302 (3)	0.4314 (3)	0.26348 (8)	0.0492 (7)
C9	0.1415 (4)	0.3453 (3)	0.22735 (9)	0.0571 (7)
H9	0.2781	0.2919	0.2366	0.068*
C10	0.0495 (4)	0.3389 (3)	0.17768 (10)	0.0591 (7)
H10	0.1266	0.2834	0.1535	0.071*
C11	−0.1566 (4)	0.4140 (3)	0.16318 (9)	0.0549 (7)
C12	−0.2636 (4)	0.5008 (3)	0.19962 (10)	0.0605 (7)
H12	−0.4012	0.5527	0.1905	0.073*
C13	−0.1715 (4)	0.5122 (3)	0.24905 (9)	0.0579 (7)
H13	−0.2446	0.5741	0.2728	0.069*
C14	−0.2612 (5)	0.4005 (4)	0.10953 (11)	0.0718 (8)
H14A	−0.1757	0.3214	0.0908	0.086*
H14B	−0.2651	0.5154	0.0940	0.086*
H14C	−0.4099	0.3559	0.1094	0.086*

	U11	U22	U33	U12	U13	U23
Cl1	0.0931 (9)	0.1079 (9)	0.0595 (8)	−0.0047 (4)	−0.0318 (5)	0.0080 (3)
O1	0.0735 (12)	0.0844 (13)	0.0496 (12)	0.0203 (9)	−0.0187 (8)	−0.0115 (9)
O2	0.0671 (12)	0.0793 (12)	0.0480 (11)	0.0089 (8)	−0.0050 (7)	−0.0095 (8)
C1	0.0570 (13)	0.0664 (13)	0.0460 (14)	0.0066 (9)	−0.0130 (9)	−0.0050 (10)
C2	0.0586 (14)	0.0753 (15)	0.0522 (15)	−0.0014 (10)	−0.0054 (10)	0.0072 (12)
C3	0.0543 (13)	0.0703 (15)	0.0644 (16)	−0.0030 (10)	−0.0135 (10)	0.0029 (12)
C4	0.0653 (15)	0.0640 (14)	0.0518 (15)	0.0026 (9)	−0.0152 (10)	0.0020 (10)
C5	0.0730 (16)	0.0801 (17)	0.0532 (16)	−0.0130 (12)	−0.0069 (12)	0.0089 (12)
C6	0.0609 (15)	0.0791 (16)	0.0637 (17)	−0.0128 (11)	−0.0148 (11)	−0.0027 (13)
C7	0.0480 (12)	0.0595 (13)	0.0471 (13)	−0.0029 (8)	−0.0061 (9)	−0.0003 (9)
C8	0.0506 (11)	0.0511 (11)	0.0439 (13)	−0.0028 (7)	−0.0058 (8)	0.0004 (8)
C9	0.0525 (13)	0.0604 (12)	0.0557 (14)	0.0063 (9)	−0.0076 (9)	−0.0049 (10)
C10	0.0635 (15)	0.0665 (14)	0.0458 (13)	0.0082 (10)	−0.0025 (10)	−0.0061 (10)
C11	0.0635 (13)	0.0499 (11)	0.0481 (14)	−0.0014 (8)	−0.0103 (10)	0.0022 (9)
C12	0.0555 (13)	0.0675 (14)	0.0556 (14)	0.0098 (9)	−0.0085 (10)	0.0043 (11)
C13	0.0607 (14)	0.0665 (14)	0.0452 (13)	0.0081 (9)	−0.0012 (9)	−0.0032 (10)
C14	0.0862 (19)	0.0737 (16)	0.0512 (16)	0.0040 (12)	−0.0150 (12)	−0.0004 (12)

Cl1—C4	1.740 (3)	C8—C13	1.384 (3)
O1—C7	1.350 (3)	C8—C9	1.386 (3)
O1—C1	1.403 (3)	C9—C10	1.378 (3)
O2—C7	1.193 (3)	C9—H9	0.9300
C1—C6	1.362 (4)	C10—C11	1.389 (3)
C1—C2	1.376 (4)	C10—H10	0.9300
C2—C3	1.383 (4)	C11—C12	1.380 (4)
C2—H2	0.9300	C11—C14	1.501 (3)
C3—C4	1.359 (4)	C12—C13	1.374 (4)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.364 (4)	C13—H13	0.9300
C5—C6	1.385 (4)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
C7—C8	1.484 (3)
C7—O1—C1	117.12 (18)	C13—C8—C7	118.57 (19)
C6—C1—C2	121.6 (3)	C9—C8—C7	122.0 (2)
C6—C1—O1	120.9 (2)	C10—C9—C8	119.8 (2)
C2—C1—O1	117.4 (2)	C10—C9—H9	120.1
C1—C2—C3	118.6 (2)	C8—C9—H9	120.1
C1—C2—H2	120.7	C9—C10—C11	121.1 (2)
C3—C2—H2	120.7	C9—C10—H10	119.4
C4—C3—C2	119.6 (2)	C11—C10—H10	119.4
C4—C3—H3	120.2	C12—C11—C10	118.1 (2)
C2—C3—H3	120.2	C12—C11—C14	120.8 (2)
C3—C4—C5	121.9 (3)	C10—C11—C14	121.1 (2)
C3—C4—Cl1	119.1 (2)	C13—C12—C11	121.5 (2)
C5—C4—Cl1	119.0 (2)	C13—C12—H12	119.2
C4—C5—C6	118.9 (3)	C11—C12—H12	119.2
C4—C5—H5	120.5	C12—C13—C8	119.9 (2)
C6—C5—H5	120.5	C12—C13—H13	120.0
C1—C6—C5	119.4 (2)	C8—C13—H13	120.0
C1—C6—H6	120.3	C11—C14—H14A	109.5
C5—C6—H6	120.3	C11—C14—H14B	109.5
O2—C7—O1	123.2 (2)	H14A—C14—H14B	109.5
O2—C7—C8	125.2 (2)	C11—C14—H14C	109.5
O1—C7—C8	111.57 (19)	H14A—C14—H14C	109.5
C13—C8—C9	119.5 (2)	H14B—C14—H14C	109.5
C7—O1—C1—C6	79.0 (3)	O2—C7—C8—C13	−13.8 (3)
C7—O1—C1—C2	−105.3 (3)	O1—C7—C8—C13	167.3 (2)
C6—C1—C2—C3	−0.2 (4)	O2—C7—C8—C9	165.9 (2)
O1—C1—C2—C3	−175.8 (2)	O1—C7—C8—C9	−12.9 (3)
C1—C2—C3—C4	0.1 (4)	C13—C8—C9—C10	−0.8 (3)
C2—C3—C4—C5	0.1 (4)	C7—C8—C9—C10	179.5 (2)
C2—C3—C4—Cl1	179.36 (19)	C8—C9—C10—C11	−1.5 (4)
C3—C4—C5—C6	−0.2 (5)	C9—C10—C11—C12	2.2 (4)
Cl1—C4—C5—C6	−179.4 (2)	C9—C10—C11—C14	−177.4 (2)
C2—C1—C6—C5	0.1 (4)	C10—C11—C12—C13	−0.5 (4)
O1—C1—C6—C5	175.6 (2)	C14—C11—C12—C13	179.1 (2)
C4—C5—C6—C1	0.1 (5)	C11—C12—C13—C8	−1.8 (4)
C1—O1—C7—O2	1.1 (3)	C9—C8—C13—C12	2.5 (4)
C1—O1—C7—C8	179.94 (19)	C7—C8—C13—C12	−177.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2i	0.93	2.51	3.212 (3)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2i	0.93	2.51	3.212 (3)	132

Symmetry code: (i) .