Crystal structure of 3-(2,5-di-meth-oxy-phen-yl)propionic acid.

In the crystal of the title compound, C11H14O4, the aromatic ring is almost coplanar with the 2-position meth-oxy group with which it subtends a dihedral of 0.54 (2)°, while the 5-position meth-oxy group makes a corresponding dihedral angle of just 5.30 (2)°. The angle between the mean planes of the aromatic ring and the propionic acid group is 78.56 (2)°. The fully extended propionic side chain is in a trans configuration with a C-C-C-C torsion angle of -172.25 (7)°. In the crystal, hydrogen bonding is limited to dimer formation via R 2 (2)(8) rings. The hydrogen-bonded dimers are stacked along the b axis. The average planes of the two benzene rings in a dimer are parallel to each other, but at an offset of 4.31 (2) Å. Within neighbouring dimers along the [101] direction, the average mol-ecular benzene planes are almost perpendicular to each other, with a dihedral angle of 85.33 (2)°.

Related literature

For another preparation method of the title compound, see: Anliker et al. (1957 ▸). For crystal structures of phenyl­propionic acids, see: Das et al. (2012 ▸). For the application of the title compound as a starting material for 19-norsteroidal derivatives, see: Anliker et al. (1957 ▸); and as a starting material for amido­ethyl­quinones, see: Bremer et al. (2014 ▸).

Experimental

Crystal data

C11H14O4

M = 210.22

Monoclinic,

a = 24.3212 (10) Å

b = 4.6512 (2) Å

c = 19.7411 (8) Å

β = 109.1782 (6)°

V = 2109.23 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.3 × 0.1 × 0.02 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▸) T min = 0.604, T max = 0.746

20284 measured reflections

3224 independent reflections

2927 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.107

S = 1.05

3224 reflections

142 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2013 ▸); cell refinement: SAINT (Bruker, 2013 ▸); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2007 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: PLATON (Spek, 2009 ▸) and Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015007641/qm2110sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015007641/qm2110Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015007641/qm2110Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015007641/qm2110fig1.tif

A view of title compound mol­ecule with the atom-numbering scheme. Displacement ellipsoids are shown at the 50% probability level.

CCDC reference: 1060285

Additional supporting information: crystallographic information; 3D view; checkCIF report

C11H14O4	Dx = 1.324 Mg m−3
Mr = 210.22	Melting point = 339–340 K
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 24.3212 (10) Å	Cell parameters from 9914 reflections
b = 4.6512 (2) Å	θ = 2.3–31.2°
c = 19.7411 (8) Å	µ = 0.10 mm−1
β = 109.1782 (6)°	T = 100 K
V = 2109.23 (15) Å3	Bar, clear light colourless
Z = 8	0.3 × 0.1 × 0.02 mm
F(000) = 896

Bruker APEXII CCD diffractometer	2927 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.028
Absorption correction: multi-scan (SADABS; Bruker, 2013)	θmax = 31.3°, θmin = 1.8°
Tmin = 0.604, Tmax = 0.746	h = −35→34
20284 measured reflections	k = −6→6
3224 independent reflections	l = −27→28

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0556P)2 + 1.4383P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3224 reflections	Δρmax = 0.44 e Å−3
142 parameters	Δρmin = −0.18 e Å−3
0 restraints

Experimental. SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1419 before and 0.0438 after correction. The Ratio of minimum to maximum transmission is 0.8088. The λ/2 correction factor is 0.0015.

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.

	x	y	z	Uiso*/Ueq
C1	0.36178 (4)	0.50978 (18)	0.70073 (5)	0.01639 (17)
C10	0.44839 (4)	0.3697 (3)	0.79439 (5)	0.0289 (2)
C11	0.14931 (4)	0.2622 (2)	0.61260 (5)	0.02223 (19)
C2	0.32768 (4)	0.32755 (19)	0.72601 (5)	0.01806 (17)
C3	0.26774 (4)	0.30632 (18)	0.69042 (5)	0.01692 (17)
C4	0.24216 (4)	0.47152 (18)	0.62979 (5)	0.01575 (16)
C5	0.27657 (4)	0.65750 (18)	0.60495 (4)	0.01568 (16)
C6	0.33612 (4)	0.67778 (17)	0.63904 (4)	0.01468 (16)
C7	0.37340 (4)	0.86255 (18)	0.60859 (5)	0.01664 (16)
C8	0.39755 (4)	0.67941 (18)	0.56036 (5)	0.01553 (16)
C9	0.44172 (3)	0.82948 (18)	0.53467 (4)	0.01464 (16)
H10A	0.4311	0.4146	0.8315	0.043*
H10B	0.4901	0.4129	0.8124	0.043*
H10C	0.4427	0.1653	0.7820	0.043*
H11A	0.1506	0.3038	0.6618	0.033*
H11B	0.1648	0.0690	0.6106	0.033*
H11C	0.1090	0.2724	0.5803	0.033*
H2	0.3452	0.2162	0.7679	0.022*
H3	0.2447	0.1796	0.7077	0.020*
H4	0.4791 (8)	0.795 (4)	0.4682 (10)	0.049 (5)*
H5	0.2587	0.7724	0.5638	0.019*
H7A	0.4059	0.9461	0.6481	0.020*
H7B	0.3498	1.0224	0.5804	0.020*
H8A	0.4156	0.5046	0.5871	0.019*
H8B	0.3647	0.6170	0.5181	0.019*
O1	0.42100 (3)	0.53955 (17)	0.73202 (4)	0.02384 (16)
O2	0.18373 (3)	0.46840 (16)	0.59092 (4)	0.02300 (16)
O3	0.46906 (3)	1.04245 (15)	0.56342 (4)	0.02097 (15)
O4	0.44928 (3)	0.70388 (15)	0.47828 (4)	0.02040 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0167 (4)	0.0191 (4)	0.0150 (4)	0.0013 (3)	0.0074 (3)	−0.0003 (3)
C10	0.0211 (4)	0.0448 (6)	0.0197 (4)	0.0072 (4)	0.0049 (3)	0.0065 (4)
C11	0.0206 (4)	0.0207 (4)	0.0263 (4)	−0.0063 (3)	0.0089 (3)	−0.0017 (3)
C2	0.0221 (4)	0.0190 (4)	0.0149 (4)	0.0013 (3)	0.0086 (3)	0.0031 (3)
C3	0.0218 (4)	0.0159 (4)	0.0162 (4)	−0.0015 (3)	0.0104 (3)	0.0008 (3)
C4	0.0170 (4)	0.0154 (3)	0.0162 (4)	−0.0009 (3)	0.0073 (3)	−0.0010 (3)
C5	0.0196 (4)	0.0144 (3)	0.0148 (3)	0.0004 (3)	0.0081 (3)	0.0015 (3)
C6	0.0190 (4)	0.0130 (3)	0.0155 (4)	0.0002 (3)	0.0103 (3)	−0.0010 (3)
C7	0.0201 (4)	0.0144 (3)	0.0200 (4)	−0.0012 (3)	0.0127 (3)	−0.0008 (3)
C8	0.0166 (4)	0.0159 (4)	0.0172 (4)	−0.0024 (3)	0.0099 (3)	−0.0016 (3)
C9	0.0137 (3)	0.0159 (4)	0.0160 (3)	0.0007 (3)	0.0072 (3)	−0.0003 (3)
O1	0.0167 (3)	0.0334 (4)	0.0207 (3)	0.0005 (3)	0.0053 (2)	0.0055 (3)
O2	0.0176 (3)	0.0258 (3)	0.0242 (3)	−0.0045 (2)	0.0049 (3)	0.0060 (3)
O3	0.0239 (3)	0.0205 (3)	0.0238 (3)	−0.0077 (2)	0.0150 (3)	−0.0069 (2)
O4	0.0208 (3)	0.0229 (3)	0.0233 (3)	−0.0074 (2)	0.0151 (3)	−0.0086 (2)

C10—H10C	0.9800	C6—C5	1.3854 (12)
C10—H10B	0.9800	C7—H7B	0.9900
C10—H10A	0.9800	C7—H7A	0.9900
C11—H11C	0.9800	C8—C9	1.5019 (11)
C11—H11B	0.9800	C8—C7	1.5312 (11)
C11—H11A	0.9800	C8—H8B	0.9900
C2—C1	1.3882 (12)	C8—H8A	0.9900
C2—H2	0.9500	O1—C10	1.4299 (12)
C3—C4	1.3858 (12)	O1—C1	1.3751 (10)
C3—C2	1.3985 (12)	O2—C11	1.4278 (11)
C3—H3	0.9500	O2—C4	1.3756 (10)
C5—C4	1.3995 (11)	O3—C9	1.2238 (10)
C5—H5	0.9500	O4—H4	0.917 (18)
C6—C1	1.4085 (12)	O4—C9	1.3224 (10)
C6—C7	1.5101 (11)
C1—C2—H2	119.7	C9—C8—H8B	108.6
C1—C2—C3	120.65 (8)	C9—C8—H8A	108.6
C1—C6—C7	120.43 (8)	C9—O4—H4	108.5 (11)
C1—O1—C10	117.01 (7)	H10A—C10—H10C	109.5
C2—C1—C6	120.15 (8)	H10A—C10—H10B	109.5
C2—C3—H3	120.2	H10B—C10—H10C	109.5
C3—C4—C5	119.66 (8)	H11A—C11—H11C	109.5
C3—C2—H2	119.7	H11A—C11—H11B	109.5
C4—C5—H5	119.3	H11B—C11—H11C	109.5
C4—C3—C2	119.53 (8)	H7A—C7—H7B	108.2
C4—C3—H3	120.2	H8A—C8—H8B	107.6
C4—O2—C11	116.09 (7)	O1—C10—H10C	109.5
C5—C6—C1	118.54 (7)	O1—C10—H10B	109.5
C5—C6—C7	120.93 (7)	O1—C10—H10A	109.5
C6—C7—H7B	109.8	O1—C1—C2	124.15 (8)
C6—C7—H7A	109.8	O1—C1—C6	115.71 (7)
C6—C7—C8	109.52 (7)	O2—C11—H11C	109.5
C6—C5—C4	121.46 (8)	O2—C11—H11B	109.5
C6—C5—H5	119.3	O2—C11—H11A	109.5
C7—C8—H8B	108.6	O2—C4—C5	115.98 (7)
C7—C8—H8A	108.6	O2—C4—C3	124.36 (8)
C8—C7—H7B	109.8	O3—C9—C8	124.03 (7)
C8—C7—H7A	109.8	O3—C9—O4	122.90 (8)
C9—C8—C7	114.48 (7)	O4—C9—C8	113.05 (7)
C1—C6—C7—C8	83.52 (9)	C5—C6—C1—C2	0.36 (12)
C1—C6—C5—C4	−1.12 (12)	C5—C6—C1—O1	179.97 (7)
C10—O1—C1—C2	0.15 (13)	C5—C6—C7—C8	−92.96 (9)
C10—O1—C1—C6	−179.45 (8)	C6—C5—C4—C3	0.97 (13)
C11—O2—C4—C5	175.08 (8)	C6—C5—C4—O2	−179.31 (7)
C11—O2—C4—C3	−5.21 (13)	C7—C8—C9—O3	19.85 (12)
C2—C3—C4—C5	−0.03 (13)	C7—C8—C9—O4	−161.63 (7)
C2—C3—C4—O2	−179.73 (8)	C7—C6—C1—C2	−176.20 (8)
C3—C2—C1—C6	0.56 (13)	C7—C6—C1—O1	3.41 (11)
C3—C2—C1—O1	−179.02 (8)	C7—C6—C5—C4	175.42 (7)
C4—C3—C2—C1	−0.73 (13)	C9—C8—C7—C6	−172.25 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3i	0.92 (2)	1.75 (2)	2.6624 (11)	172.1 (18)

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O4H4O3i	0.92(2)	1.75(2)	2.6624(11)	172.1(18)

Symmetry code: (i) .