2,4-Dichloro­benzyl 2-meth­oxy­benzoate

Isloor, A.M.; Garudachari, B.; Gerber, T.; Hosten, E.; Betz, R.

doi:10.1107/S1600536813006156

organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o509

doi:10.1107/S1600536813006156

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2,4-Dichlorobenzyl 2-methoxybenzoate

Arun M. Isloor,^a B. Garudachari,^a Thomas Gerber,^b Eric Hosten ^b and Richard Betz ^b ^*

^aNational Institute of Technology-Karnataka, Department of Chemistry, Surathkal, Mangalore 575 025, India, and ^bNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
^*Correspondence e-mail: richard.betz@webmail.co.za

(Received 26 February 2013; accepted 4 March 2013; online 9 March 2013)

In the title compound, C₁₅H₁₂Cl₂O₃, the aromatic rings make a dihedral angle of 10.78 (4)°. In the molecule, there is a short C—H⋯O contact. In the crystal, C—H⋯O contacts connect the molecules into C(7)C(8) chains along the b axis. The shortest intercentroid distance between two benzoic acid aromatic systems is 3.7416 (8) Å.

Related literature

For pharmacological properties of phenyl benzoates, see: Oxford et al. (2005 ); Ostergaard (1994 ). For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995 ); Etter et al. (1990 ).

Experimental

Crystal data

C₁₅H₁₂Cl₂O₃
M_r = 311.15
Monoclinic, P 2₁ /c
a = 12.1816 (5) Å
b = 15.2481 (6) Å
c = 7.4207 (4) Å
β = 99.299 (2)°
V = 1360.25 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.48 mm⁻¹
T = 200 K
0.38 × 0.37 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.847, T_max = 0.982
12933 measured reflections
3379 independent reflections
2868 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.080
S = 1.03
3379 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O2ⁱ	0.98	2.59	3.5433 (18)	165
C15—H15⋯O2ⁱ	0.95	2.51	3.3945 (15)	154
C16—H16⋯O3	0.95	2.48	3.3989 (15)	163
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813006156/ng5318sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813006156/ng5318Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813006156/ng5318Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536813006156/ng5318Isup4.cml

checkCIF report

Comment top

For decades, phenyl benzoate derivatives have found ample application in the identification of organic acids. 2,4-Dichlorobenzyl derivatives show pharmacological activity such as acting as mild antiseptics and showing the ability to kill bacteria and viruses associated with mouth and throat infections (Oxford et al., 2005; Ostergaard 1994). In continuation of our research focused on the crystal structures of medical compounds, the title compound was synthesized.

The molecule is essentially flat. The atom deviating most from the least-squares plane defined by all non-hydrogen atoms is the chlorine atom in para position to the benzyloxy moiety with a deviation of 0.237 (1) Å. The least-squares planes defined by the respective carbon atoms of the aromatic systems intersect at an angle of 10.78 (4) ° (Fig. 1).

In the crystal, intermolecular C–H···O contacts whose range falls by more than 0.1 Å below the sum of van-der-Waals radii are observed. These are established between one of the hydrogen atoms of the methoxy group as well as one of the two hydrogen atoms in ortho position to the chlorine atom in para position to the benzyloxy group and chelate the ketonic oxygen atom of the ester moiety. In total, the molecules are connected to chains along the crystallographic b axis. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for these contacts is C¹₁(7)C¹₁(8) on the unary level. Information about metrical parameters as well as the symmetry of those contacts has been summarized in Table 1. The shortest intercentroid distance between two aromatic systems was measured at 3.7416 (8) Å and is apparent between the benzoic acid moiety and its symmetry-generated equivalent (Fig. 2).

The packing of the title compound in the crystal structure is shown in Figure 3.

Related literature top

For pharmacological properties of phenyl benzoates, see: Oxford et al. (2005); Ostergaard (1994). For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995); Etter et al. (1990).

Experimental top

A mixture of 1-(bromomethyl)-2,4-dichlorobenzene (0.1 g, 0.0004 mol), potassium carbonate (0.062 g, 0.00045 mol) and 2-methoxybenzoic acid (0.068 g, 0.00045 mol) in dimethylformamide (5 ml) was stirred at 60 °C for 2 h. After completion of the reaction, the reaction mixture was poured into ice-cold water. The solid product obtained was filtered, washed with water and recrystallized from ethanol (yield: 0.120 g, 93.0%).

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level).
	Fig. 2. Intermolecular contacts, viewed along [0 0 1]. Symmetry operators: ⁱ -x + 1, y + 1/2, -z + 1/2; ⁱⁱ -x + 1, y - 1/2, -z + 1/2.
	Fig. 3. Molecular packing of the title compound, viewed along [0 1 0] (anisotropic displacement ellipsoids drawn at 50% probability level).

2,4-Dichlorobenzyl 2-methoxybenzoate top

Crystal data top

C₁₅H₁₂Cl₂O₃	F(000) = 640
M_r = 311.15	D_x = 1.519 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 376–374 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.1816 (5) Å	Cell parameters from 6565 reflections
b = 15.2481 (6) Å	θ = 2.7–28.3°
c = 7.4207 (4) Å	µ = 0.48 mm⁻¹
β = 99.299 (2)°	T = 200 K
V = 1360.25 (11) Å³	Block, colourless
Z = 4	0.38 × 0.37 × 0.15 mm

Data collection top

Bruker APEXII CCD diffractometer	3379 independent reflections
Radiation source: fine-focus sealed tube	2868 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
ϕ and ω scans	θ_max = 28.4°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→16
T_min = 0.847, T_max = 0.982	k = −20→20
12933 measured reflections	l = −9→9

Refinement top

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0407P)² + 0.3593P] where P = (F_o² + 2F_c²)/3
3379 reflections	(Δ/σ)_max = 0.001
182 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₅H₁₂Cl₂O₃	V = 1360.25 (11) Å³
M_r = 311.15	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.1816 (5) Å	µ = 0.48 mm⁻¹
b = 15.2481 (6) Å	T = 200 K
c = 7.4207 (4) Å	0.38 × 0.37 × 0.15 mm
β = 99.299 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3379 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2868 reflections with I > 2σ(I)
T_min = 0.847, T_max = 0.982	R_int = 0.015
12933 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.03	Δρ_max = 0.26 e Å⁻³
3379 reflections	Δρ_min = −0.23 e Å⁻³
182 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.83729 (2)	0.13621 (2)	0.22173 (5)	0.03453 (10)
Cl2	0.93726 (3)	0.47791 (2)	0.20393 (6)	0.05086 (12)
O1	0.50796 (7)	0.23368 (5)	0.32072 (13)	0.0302 (2)
O2	0.42680 (8)	0.10301 (6)	0.32410 (15)	0.0417 (2)
O3	0.39479 (7)	0.37220 (5)	0.34997 (14)	0.0354 (2)
C1	0.60253 (9)	0.19251 (7)	0.26253 (17)	0.0260 (2)
H1A	0.5802	0.1629	0.1435	0.031*
H1B	0.6354	0.1483	0.3532	0.031*
C2	0.42351 (9)	0.18141 (7)	0.34359 (16)	0.0250 (2)
C3	0.37406 (13)	0.46402 (9)	0.3289 (2)	0.0465 (4)
H3A	0.4363	0.4920	0.2823	0.070*
H3B	0.3664	0.4896	0.4473	0.070*
H3C	0.3053	0.4735	0.2425	0.070*
C11	0.68490 (9)	0.26426 (7)	0.24577 (15)	0.0234 (2)
C12	0.79427 (9)	0.24488 (7)	0.22730 (16)	0.0244 (2)
C13	0.87222 (10)	0.30935 (8)	0.21331 (17)	0.0291 (3)
H13	0.9464	0.2945	0.2012	0.035*
C14	0.83948 (10)	0.39622 (8)	0.21735 (17)	0.0303 (3)
C15	0.73151 (10)	0.41879 (8)	0.23178 (18)	0.0306 (3)
H15	0.7097	0.4786	0.2319	0.037*
C16	0.65539 (10)	0.35254 (8)	0.24611 (17)	0.0274 (2)
H16	0.5810	0.3678	0.2564	0.033*
C21	0.32638 (9)	0.22915 (7)	0.39497 (16)	0.0249 (2)
C22	0.31284 (9)	0.32091 (8)	0.39762 (16)	0.0268 (2)
C23	0.21596 (10)	0.35594 (9)	0.44706 (18)	0.0327 (3)
H23	0.2066	0.4177	0.4505	0.039*
C24	0.13359 (10)	0.30135 (10)	0.49094 (18)	0.0355 (3)
H24	0.0686	0.3260	0.5261	0.043*
C25	0.14469 (10)	0.21127 (10)	0.48428 (18)	0.0351 (3)
H25	0.0870	0.1740	0.5113	0.042*
C26	0.24091 (10)	0.17634 (8)	0.43777 (17)	0.0296 (3)
H26	0.2491	0.1144	0.4349	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02915 (16)	0.02768 (16)	0.0483 (2)	0.00585 (11)	0.01086 (13)	−0.00228 (12)
Cl2	0.03554 (19)	0.03606 (19)	0.0846 (3)	−0.00991 (14)	0.02065 (18)	0.00427 (17)
O1	0.0219 (4)	0.0242 (4)	0.0472 (5)	−0.0005 (3)	0.0138 (4)	−0.0033 (3)
O2	0.0334 (5)	0.0234 (4)	0.0723 (7)	−0.0010 (4)	0.0204 (5)	−0.0008 (4)
O3	0.0301 (4)	0.0218 (4)	0.0571 (6)	0.0015 (3)	0.0155 (4)	0.0014 (4)
C1	0.0220 (5)	0.0230 (5)	0.0345 (6)	0.0021 (4)	0.0090 (4)	−0.0009 (5)
C2	0.0220 (5)	0.0251 (5)	0.0280 (6)	−0.0011 (4)	0.0040 (4)	0.0020 (4)
C3	0.0460 (8)	0.0234 (6)	0.0740 (11)	0.0030 (6)	0.0218 (8)	0.0014 (6)
C11	0.0219 (5)	0.0261 (5)	0.0227 (5)	0.0005 (4)	0.0048 (4)	0.0003 (4)
C12	0.0244 (5)	0.0259 (5)	0.0235 (5)	0.0033 (4)	0.0052 (4)	−0.0005 (4)
C13	0.0218 (5)	0.0350 (6)	0.0318 (6)	0.0008 (5)	0.0086 (4)	0.0001 (5)
C14	0.0282 (6)	0.0295 (6)	0.0347 (6)	−0.0058 (5)	0.0092 (5)	0.0012 (5)
C15	0.0311 (6)	0.0252 (6)	0.0372 (7)	0.0006 (5)	0.0102 (5)	0.0013 (5)
C16	0.0231 (5)	0.0276 (6)	0.0329 (6)	0.0023 (4)	0.0085 (5)	0.0009 (5)
C21	0.0220 (5)	0.0277 (6)	0.0250 (6)	0.0003 (4)	0.0036 (4)	−0.0007 (4)
C22	0.0224 (5)	0.0291 (6)	0.0290 (6)	0.0003 (4)	0.0044 (4)	−0.0006 (5)
C23	0.0274 (6)	0.0362 (7)	0.0346 (7)	0.0064 (5)	0.0053 (5)	−0.0045 (5)
C24	0.0238 (6)	0.0517 (8)	0.0318 (6)	0.0049 (5)	0.0068 (5)	−0.0059 (6)
C25	0.0245 (6)	0.0493 (8)	0.0328 (7)	−0.0062 (5)	0.0089 (5)	−0.0022 (6)
C26	0.0271 (6)	0.0330 (6)	0.0293 (6)	−0.0041 (5)	0.0063 (5)	−0.0003 (5)

Geometric parameters (Å, º) top

Cl1—C12	1.7403 (12)	C13—C14	1.3849 (17)
Cl2—C14	1.7374 (12)	C13—H13	0.9500
O1—C2	1.3337 (13)	C14—C15	1.3804 (17)
O1—C1	1.4383 (13)	C15—C16	1.3869 (17)
O2—C2	1.2057 (15)	C15—H15	0.9500
O3—C22	1.3592 (14)	C16—H16	0.9500
O3—C3	1.4267 (15)	C21—C26	1.3929 (16)
C1—C11	1.5033 (15)	C21—C22	1.4093 (16)
C1—H1A	0.9900	C22—C23	1.3973 (16)
C1—H1B	0.9900	C23—C24	1.3826 (19)
C2—C21	1.4902 (16)	C23—H23	0.9500
C3—H3A	0.9800	C24—C25	1.382 (2)
C3—H3B	0.9800	C24—H24	0.9500
C3—H3C	0.9800	C25—C26	1.3811 (17)
C11—C12	1.3929 (16)	C25—H25	0.9500
C11—C16	1.3933 (16)	C26—H26	0.9500
C12—C13	1.3823 (17)

C2—O1—C1	116.68 (9)	C15—C14—Cl2	119.76 (10)
C22—O3—C3	117.96 (10)	C13—C14—Cl2	118.81 (9)
O1—C1—C11	106.55 (9)	C14—C15—C16	118.79 (11)
O1—C1—H1A	110.4	C14—C15—H15	120.6
C11—C1—H1A	110.4	C16—C15—H15	120.6
O1—C1—H1B	110.4	C15—C16—C11	121.85 (11)
C11—C1—H1B	110.4	C15—C16—H16	119.1
H1A—C1—H1B	108.6	C11—C16—H16	119.1
O2—C2—O1	122.41 (11)	C26—C21—C22	118.51 (11)
O2—C2—C21	123.93 (11)	C26—C21—C2	115.44 (10)
O1—C2—C21	113.66 (10)	C22—C21—C2	126.02 (10)
O3—C3—H3A	109.5	O3—C22—C23	122.36 (11)
O3—C3—H3B	109.5	O3—C22—C21	118.37 (10)
H3A—C3—H3B	109.5	C23—C22—C21	119.27 (11)
O3—C3—H3C	109.5	C24—C23—C22	120.50 (12)
H3A—C3—H3C	109.5	C24—C23—H23	119.8
H3B—C3—H3C	109.5	C22—C23—H23	119.8
C12—C11—C16	117.15 (11)	C25—C24—C23	120.74 (12)
C12—C11—C1	121.04 (10)	C25—C24—H24	119.6
C16—C11—C1	121.81 (10)	C23—C24—H24	119.6
C13—C12—C11	122.41 (11)	C26—C25—C24	118.96 (12)
C13—C12—Cl1	117.53 (9)	C26—C25—H25	120.5
C11—C12—Cl1	120.05 (9)	C24—C25—H25	120.5
C12—C13—C14	118.35 (11)	C25—C26—C21	121.99 (12)
C12—C13—H13	120.8	C25—C26—H26	119.0
C14—C13—H13	120.8	C21—C26—H26	119.0
C15—C14—C13	121.43 (11)

C2—O1—C1—C11	179.67 (10)	O2—C2—C21—C26	6.06 (18)
C1—O1—C2—O2	2.90 (17)	O1—C2—C21—C26	−173.90 (10)
C1—O1—C2—C21	−177.14 (10)	O2—C2—C21—C22	−171.70 (12)
O1—C1—C11—C12	167.09 (10)	O1—C2—C21—C22	8.34 (16)
O1—C1—C11—C16	−13.58 (15)	C3—O3—C22—C23	−7.76 (18)
C16—C11—C12—C13	1.25 (18)	C3—O3—C22—C21	171.63 (12)
C1—C11—C12—C13	−179.38 (11)	C26—C21—C22—O3	−177.87 (11)
C16—C11—C12—Cl1	−178.92 (9)	C2—C21—C22—O3	−0.17 (18)
C1—C11—C12—Cl1	0.44 (16)	C26—C21—C22—C23	1.53 (17)
C11—C12—C13—C14	−0.22 (18)	C2—C21—C22—C23	179.23 (11)
Cl1—C12—C13—C14	179.96 (9)	O3—C22—C23—C24	178.65 (12)
C12—C13—C14—C15	−1.10 (19)	C21—C22—C23—C24	−0.73 (18)
C12—C13—C14—Cl2	178.88 (9)	C22—C23—C24—C25	−0.9 (2)
C13—C14—C15—C16	1.3 (2)	C23—C24—C25—C26	1.7 (2)
Cl2—C14—C15—C16	−178.68 (10)	C24—C25—C26—C21	−0.90 (19)
C14—C15—C16—C11	−0.19 (19)	C22—C21—C26—C25	−0.73 (18)
C12—C11—C16—C15	−1.04 (18)	C2—C21—C26—C25	−178.67 (11)
C1—C11—C16—C15	179.60 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O2ⁱ	0.98	2.59	3.5433 (18)	165
C15—H15···O2ⁱ	0.95	2.51	3.3945 (15)	154
C16—H16···O3	0.95	2.48	3.3989 (15)	163

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂Cl₂O₃
M_r	311.15
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	12.1816 (5), 15.2481 (6), 7.4207 (4)
β (°)	99.299 (2)
V (Å³)	1360.25 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.48
Crystal size (mm)	0.38 × 0.37 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.847, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	12933, 3379, 2868
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.080, 1.03
No. of reflections	3379
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.23

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O2ⁱ	0.98	2.59	3.5433 (18)	165.0
C15—H15···O2ⁱ	0.95	2.51	3.3945 (15)	154.4
C16—H16···O3	0.95	2.48	3.3989 (15)	163.1

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Acknowledgements

AMI thanks Professor Swapan Bhattacharya, Director of the National Institute of Technology Karnataka, Surathkal, India, for encouragement and for providing research facilities. He also thanks the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for the Young Scientist award.

References

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