Methyl 3-(4-methoxy-benzo-yl)propionate.

The asymmetric unit of the title compound, C(12)H(14)O(3), contains two independent mol-ecules, in which the benzene rings are oriented at a dihedral angle of 72.08 (3)°. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers. There are also C-H⋯π contacts between aromatic CH groups and the benzene rings.

Related literature

For general background, see: Hashem et al. (2007 ▶); Husain et al.(2005 ▶). For a related structure, see: Ali et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C12H14O3

M = 206.23

Monoclinic,

a = 34.762 (4) Å

b = 5.2861 (7) Å

c = 27.752 (3) Å

β = 117.182 (2)°

V = 4536.5 (9) Å3

Z = 16

Mo Kα radiation

μ = 0.09 mm−1

T = 294 (2) K

0.28 × 0.26 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.798, T max = 0.980

13099 measured reflections

5456 independent reflections

3364 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.174

S = 1.01

5456 reflections

272 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; 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/S1600536808037720/hk2571sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037720/hk2571Isup2.hkl

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

C12H14O3	F000 = 1760
Mr = 206.23	Dx = 1.208 Mg m−3
Monoclinic, C2/c	Melting point: 308(1) K
Hall symbol: -C 2yc	Mo Kα radiation λ = 0.71073 Å
a = 34.762 (4) Å	Cell parameters from 2335 reflections
b = 5.2861 (7) Å	θ = 5.3–18.6º
c = 27.752 (3) Å	µ = 0.09 mm−1
β = 117.182 (2)º	T = 294 (2) K
V = 4536.5 (9) Å3	Block, colorless
Z = 16	0.28 × 0.26 × 0.23 mm

Bruker SMART CCD area-detector diffractometer	5456 independent reflections
Radiation source: fine-focus sealed tube	3364 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.025
T = 294(2) K	θmax = 28.3º
ω and φ scans	θmin = 2.4º
Absorption correction: multi-scan(SADABS; Bruker, 1998)	h = −37→45
Tmin = 0.798, Tmax = 0.980	k = −6→6
13099 measured reflections	l = −37→27

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.049	w = 1/[σ2(Fo2) + (0.0886P)2 + 0.985P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.174	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.25 e Å−3
5456 reflections	Δρmin = −0.18 e Å−3
272 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: 0.0021 (4)
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
O1	0.17237 (4)	0.1342 (3)	0.28466 (5)	0.0856 (4)
O2	0.07042 (4)	0.0750 (3)	0.24528 (5)	0.0908 (4)
O3	0.08802 (4)	−0.0612 (3)	0.32828 (5)	0.0849 (4)
O4	0.07570 (4)	0.7301 (3)	−0.03309 (5)	0.0848 (4)
O5	0.17800 (5)	0.7032 (3)	0.00217 (5)	0.0987 (5)
O6	0.16293 (5)	0.6067 (3)	−0.08206 (5)	0.0923 (5)
C1	0.23566 (7)	0.1919 (5)	0.09882 (8)	0.0915 (6)
H1A	0.2259	0.0684	0.0703	0.137*
H1B	0.2665	0.1819	0.1196	0.137*
H1C	0.2277	0.3579	0.0834	0.137*
C2	0.21493 (5)	0.1408 (3)	0.13526 (6)	0.0633 (4)
C3	0.22438 (5)	0.2949 (3)	0.17972 (6)	0.0633 (4)
H3A	0.2427	0.4326	0.1860	0.076*
C4	0.20724 (5)	0.2485 (3)	0.21467 (6)	0.0592 (4)
H4A	0.2144	0.3537	0.2444	0.071*
C5	0.17922 (4)	0.0452 (3)	0.20601 (6)	0.0527 (3)
C6	0.16911 (5)	−0.1061 (3)	0.16102 (6)	0.0622 (4)
H6A	0.1502	−0.2413	0.1541	0.075*
C7	0.18676 (6)	−0.0588 (3)	0.12648 (6)	0.0683 (4)
H7A	0.1796	−0.1633	0.0966	0.082*
C8	0.16253 (5)	−0.0046 (3)	0.24590 (6)	0.0584 (4)
C9	0.13441 (6)	−0.2324 (3)	0.23814 (7)	0.0695 (4)
H9A	0.1499	−0.3823	0.2367	0.083*
H9B	0.1087	−0.2176	0.2036	0.083*
C10	0.12090 (6)	−0.2663 (4)	0.28236 (8)	0.0749 (5)
H10A	0.1070	−0.4296	0.2779	0.090*
H10B	0.1465	−0.2659	0.3172	0.090*
C11	0.09074 (5)	−0.0647 (3)	0.28213 (7)	0.0645 (4)
C12	0.05918 (7)	0.1240 (5)	0.33221 (9)	0.0975 (7)
H12A	0.0597	0.1109	0.3670	0.146*
H12B	0.0303	0.0942	0.3043	0.146*
H12C	0.0683	0.2904	0.3280	0.146*
C13	0.01362 (6)	0.5636 (5)	0.15220 (8)	0.0921 (6)
H13A	−0.0064	0.7016	0.1435	0.138*
H13B	0.0360	0.5820	0.1887	0.138*
H13C	−0.0013	0.4068	0.1488	0.138*
C14	0.03334 (5)	0.5641 (3)	0.11394 (7)	0.0663 (4)
C15	0.02252 (6)	0.7474 (4)	0.07450 (7)	0.0760 (5)
H15A	0.0030	0.8735	0.0719	0.091*
C16	0.04011 (5)	0.7474 (3)	0.03875 (7)	0.0717 (5)
H16A	0.0321	0.8726	0.0124	0.086*
C17	0.06942 (5)	0.5640 (3)	0.04171 (6)	0.0572 (4)
C18	0.08110 (6)	0.3822 (3)	0.08218 (7)	0.0708 (5)
H18A	0.1011	0.2582	0.0855	0.085*
C19	0.06326 (6)	0.3842 (4)	0.11747 (7)	0.0750 (5)
H19A	0.0716	0.2612	0.1443	0.090*
C20	0.08610 (5)	0.5643 (3)	0.00094 (6)	0.0631 (4)
C21	0.11550 (6)	0.3537 (4)	0.00230 (8)	0.0770 (5)
H21A	0.1011	0.1937	−0.0001	0.092*
H21B	0.1413	0.3577	0.0369	0.092*
C22	0.12873 (7)	0.3661 (4)	−0.04260 (9)	0.0868 (6)
H22A	0.1424	0.2072	−0.0435	0.104*
H22B	0.1029	0.3841	−0.0769	0.104*
C23	0.15891 (6)	0.5766 (4)	−0.03702 (7)	0.0709 (5)
C24	0.19204 (7)	0.8028 (5)	−0.08167 (9)	0.1000 (7)
H24A	0.1923	0.8066	−0.1161	0.150*
H24B	0.2207	0.7686	−0.0536	0.150*
H24C	0.1825	0.9635	−0.0751	0.150*

	U11	U22	U33	U12	U13	U23
O1	0.1036 (9)	0.0928 (10)	0.0726 (8)	−0.0206 (8)	0.0509 (7)	−0.0246 (7)
O2	0.1021 (9)	0.1002 (11)	0.0765 (8)	0.0355 (8)	0.0462 (7)	0.0253 (7)
O3	0.0976 (9)	0.0987 (10)	0.0740 (8)	0.0180 (8)	0.0528 (7)	0.0146 (7)
O4	0.1052 (9)	0.0775 (9)	0.0786 (8)	0.0147 (7)	0.0478 (7)	0.0208 (7)
O5	0.1186 (11)	0.1140 (12)	0.0730 (8)	−0.0327 (9)	0.0522 (8)	−0.0226 (8)
O6	0.1053 (10)	0.1139 (12)	0.0700 (8)	−0.0022 (9)	0.0507 (7)	−0.0093 (8)
C1	0.0910 (13)	0.1117 (17)	0.0855 (13)	0.0006 (12)	0.0522 (11)	0.0034 (12)
C2	0.0589 (9)	0.0697 (10)	0.0598 (9)	0.0106 (7)	0.0259 (7)	0.0069 (8)
C3	0.0572 (8)	0.0606 (9)	0.0672 (9)	−0.0006 (7)	0.0242 (7)	0.0019 (8)
C4	0.0594 (8)	0.0547 (9)	0.0586 (8)	0.0005 (7)	0.0225 (7)	−0.0069 (7)
C5	0.0541 (7)	0.0487 (8)	0.0509 (7)	0.0080 (6)	0.0201 (6)	0.0019 (6)
C6	0.0713 (9)	0.0529 (9)	0.0595 (9)	−0.0035 (7)	0.0273 (7)	−0.0051 (7)
C7	0.0822 (10)	0.0653 (10)	0.0573 (9)	−0.0004 (8)	0.0316 (8)	−0.0091 (7)
C8	0.0605 (8)	0.0548 (9)	0.0576 (8)	0.0072 (7)	0.0249 (7)	−0.0006 (7)
C9	0.0812 (11)	0.0573 (10)	0.0812 (11)	0.0029 (8)	0.0466 (9)	−0.0008 (8)
C10	0.0902 (12)	0.0629 (10)	0.0844 (12)	0.0094 (9)	0.0510 (10)	0.0145 (9)
C11	0.0683 (9)	0.0653 (10)	0.0650 (9)	−0.0016 (8)	0.0348 (8)	0.0059 (8)
C12	0.1033 (15)	0.1157 (18)	0.0954 (15)	0.0148 (14)	0.0644 (13)	−0.0035 (13)
C13	0.0812 (12)	0.1145 (18)	0.0849 (13)	−0.0088 (12)	0.0416 (10)	0.0061 (12)
C14	0.0616 (9)	0.0695 (11)	0.0609 (9)	−0.0118 (8)	0.0219 (7)	−0.0007 (8)
C15	0.0741 (10)	0.0726 (12)	0.0813 (12)	0.0137 (9)	0.0355 (9)	0.0095 (9)
C16	0.0768 (10)	0.0646 (11)	0.0719 (10)	0.0135 (8)	0.0324 (9)	0.0178 (8)
C17	0.0585 (8)	0.0463 (8)	0.0573 (8)	−0.0045 (6)	0.0182 (7)	0.0001 (6)
C18	0.0784 (10)	0.0547 (9)	0.0737 (11)	0.0096 (8)	0.0301 (9)	0.0094 (8)
C19	0.0878 (12)	0.0652 (11)	0.0684 (10)	0.0022 (9)	0.0324 (9)	0.0167 (8)
C20	0.0691 (9)	0.0529 (9)	0.0616 (9)	−0.0059 (7)	0.0250 (7)	−0.0015 (7)
C21	0.0949 (12)	0.0555 (10)	0.0905 (13)	0.0031 (9)	0.0510 (11)	0.0012 (9)
C22	0.1103 (14)	0.0699 (12)	0.0914 (13)	−0.0015 (11)	0.0560 (12)	−0.0178 (10)
C23	0.0805 (11)	0.0753 (12)	0.0622 (10)	0.0100 (9)	0.0372 (9)	−0.0041 (8)
C24	0.1055 (15)	0.1219 (19)	0.0944 (15)	0.0072 (14)	0.0645 (13)	0.0115 (14)

C1—C2	1.510 (2)	C13—C14	1.504 (2)
C1—H1A	0.9600	C13—H13A	0.9600
C1—H1B	0.9600	C13—H13B	0.9600
C1—H1C	0.9600	C13—H13C	0.9600
C2—C7	1.384 (2)	C14—C15	1.379 (2)
C2—C3	1.387 (2)	C14—C19	1.379 (2)
C3—C4	1.373 (2)	C15—C16	1.383 (2)
C3—H3A	0.9300	C15—H15A	0.9300
C4—C5	1.396 (2)	C16—C17	1.382 (2)
C4—H4A	0.9300	C16—H16A	0.9300
C5—C6	1.386 (2)	C17—C18	1.390 (2)
C5—C8	1.489 (2)	C17—C20	1.489 (2)
C6—C7	1.377 (2)	C18—C19	1.378 (2)
C6—H6A	0.9300	C18—H18A	0.9300
C7—H7A	0.9300	C19—H19A	0.9300
C8—O1	1.2151 (19)	C20—O4	1.2159 (19)
C8—C9	1.503 (2)	C20—C21	1.500 (2)
C9—C10	1.511 (2)	C21—C22	1.514 (3)
C9—H9A	0.9700	C21—H21A	0.9700
C9—H9B	0.9700	C21—H21B	0.9700
C10—C11	1.493 (2)	C22—C23	1.488 (3)
C10—H10A	0.9700	C22—H22A	0.9700
C10—H10B	0.9700	C22—H22B	0.9700
C11—O2	1.1955 (19)	C23—O5	1.188 (2)
C11—O3	1.3268 (19)	C23—O6	1.329 (2)
C12—O3	1.440 (2)	C24—O6	1.445 (3)
C12—H12A	0.9600	C24—H24A	0.9600
C12—H12B	0.9600	C24—H24B	0.9600
C12—H12C	0.9600	C24—H24C	0.9600
C2—C1—H1A	109.5	C14—C13—H13B	109.5
C2—C1—H1B	109.5	H13A—C13—H13B	109.5
H1A—C1—H1B	109.5	C14—C13—H13C	109.5
C2—C1—H1C	109.5	H13A—C13—H13C	109.5
H1A—C1—H1C	109.5	H13B—C13—H13C	109.5
H1B—C1—H1C	109.5	C15—C14—C19	117.67 (16)
C7—C2—C3	117.74 (15)	C15—C14—C13	120.96 (17)
C7—C2—C1	122.31 (17)	C19—C14—C13	121.37 (17)
C3—C2—C1	119.94 (17)	C14—C15—C16	121.32 (17)
C4—C3—C2	121.40 (15)	C14—C15—H15A	119.3
C4—C3—H3A	119.3	C16—C15—H15A	119.3
C2—C3—H3A	119.3	C17—C16—C15	120.85 (16)
C3—C4—C5	120.66 (14)	C17—C16—H16A	119.6
C3—C4—H4A	119.7	C15—C16—H16A	119.6
C5—C4—H4A	119.7	C16—C17—C18	117.93 (15)
C6—C5—C4	117.99 (14)	C16—C17—C20	119.12 (14)
C6—C5—C8	122.87 (14)	C18—C17—C20	122.93 (15)
C4—C5—C8	119.11 (13)	C19—C18—C17	120.59 (16)
C7—C6—C5	120.80 (15)	C19—C18—H18A	119.7
C7—C6—H6A	119.6	C17—C18—H18A	119.7
C5—C6—H6A	119.6	C18—C19—C14	121.61 (16)
C6—C7—C2	121.38 (15)	C18—C19—H19A	119.2
C6—C7—H7A	119.3	C14—C19—H19A	119.2
C2—C7—H7A	119.3	O4—C20—C17	120.69 (15)
O1—C8—C5	120.22 (15)	O4—C20—C21	120.79 (16)
O1—C8—C9	120.82 (15)	C17—C20—C21	118.51 (14)
C5—C8—C9	118.94 (13)	C20—C21—C22	114.01 (16)
C8—C9—C10	113.66 (15)	C20—C21—H21A	108.7
C8—C9—H9A	108.8	C22—C21—H21A	108.7
C10—C9—H9A	108.8	C20—C21—H21B	108.7
C8—C9—H9B	108.8	C22—C21—H21B	108.7
C10—C9—H9B	108.8	H21A—C21—H21B	107.6
H9A—C9—H9B	107.7	C23—C22—C21	114.28 (16)
C11—C10—C9	112.96 (14)	C23—C22—H22A	108.7
C11—C10—H10A	109.0	C21—C22—H22A	108.7
C9—C10—H10A	109.0	C23—C22—H22B	108.7
C11—C10—H10B	109.0	C21—C22—H22B	108.7
C9—C10—H10B	109.0	H22A—C22—H22B	107.6
H10A—C10—H10B	107.8	O5—C23—O6	122.60 (19)
O2—C11—O3	122.84 (16)	O5—C23—C22	126.08 (17)
O2—C11—C10	125.71 (16)	O6—C23—C22	111.31 (16)
O3—C11—C10	111.44 (14)	O6—C24—H24A	109.5
O3—C12—H12A	109.5	O6—C24—H24B	109.5
O3—C12—H12B	109.5	H24A—C24—H24B	109.5
H12A—C12—H12B	109.5	O6—C24—H24C	109.5
O3—C12—H12C	109.5	H24A—C24—H24C	109.5
H12A—C12—H12C	109.5	H24B—C24—H24C	109.5
H12B—C12—H12C	109.5	C11—O3—C12	116.21 (15)
C14—C13—H13A	109.5	C23—O6—C24	116.92 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24A···O1i	0.96	2.53	3.467 (3)	164
C4—H4A···Cg1ii	0.93	3.17	3.858 (4)	133
C6—H6A···Cg2iii	0.93	3.26	4.051 (3)	144
C18—H18A···Cg1	0.93	3.20	3.940 (3)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C24—H24A⋯O1i	0.96	2.53	3.467 (3)	164
C4—H4A⋯Cg1ii	0.93	3.17	3.858 (4)	133
C6—H6A⋯Cg2iii	0.93	3.26	4.051 (3)	144
C18—H18A⋯Cg1	0.93	3.20	3.940 (3)	138

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C2–C7 and C14–C19 rings.