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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 5| May 2015| Pages o337-o338
https://doi.org/10.1107/S2056989015007641

Crystal structure of 3-(2,5-di­meth­­oxy­phen­yl)propionic acid

Bernhard Bugenhagen,a Yosef Al Jasem,b Mariam AlAzanic and Thies Thiemannc*

aInstitute of Inorganic Chemistry, University of Hamburg, Hamburg, Germany, bDepartment of Chemical Engineering, and cDepartment of Chemistry, United Arab Emirates University, AL Ain, Abu Dhabi, United Arab Emirates
*Correspondence e-mail: thies@uaeu.ac.ae

Edited by P. McArdle, National University of Ireland, Ireland (Received 12 April 2015; accepted 18 April 2015; online 25 April 2015)

In the crystal of the title compound, C11H14O4, the aromatic ring is almost coplanar with the 2-position meth­oxy group with which it subtends a dihedral of 0.54 (2)°, while the 5-position meth­oxy 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 R22(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 mol­ecular benzene planes are almost perpendicular to each other, with a dihedral angle of 85.33 (2)°.

CCDC reference: 1060285

Similar articles

1. Related literature

For another preparation method of the title compound, see: Anliker et al. (1957[Anliker, R., Lindsey, A. S., Nettleton, D. E. & Turner, R. B. Jr (1957). J. Am. Chem. Soc. 79, 220-226.]). For crystal structures of phenyl­propionic acids, see: Das et al. (2012[Das, U., Chattopadhyay, B., Mukherjee, M. & Mukherjee, A. K. (2012). Cryst. Growth Des. 12, 466-474.]). For the application of the title compound as a starting material for 19-norsteroidal derivatives, see: Anliker et al. (1957[Anliker, R., Lindsey, A. S., Nettleton, D. E. & Turner, R. B. Jr (1957). J. Am. Chem. Soc. 79, 220-226.]); and as a starting material for amido­ethyl­quinones, see: Bremer et al. (2014[Bremer, P. T., Hixon, M. S. & Janda, K. D. (2014). Bioorg. Med. Chem. 22, 3971-3981.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C11H14O4

  • Mr = 210.22

  • Monoclinic, C 2/c

  • 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

2.2. Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.604, Tmax = 0.746

  • 20284 measured reflections

  • 3224 independent reflections

  • 2927 reflections with I > 2σ(I)

  • Rint = 0.028

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

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

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2007[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609-613.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Supporting information

CCDC reference: 1060285

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989015007641/qm2110sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015007641/qm2110Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015007641/qm2110Isup3.cml

checkCIF report


Structural commentary top

The molecule of the title compound exhibits one conformation (Figure 1), unlike other analogous compounds that exhibit two conformations (e.g. 3-phenyl­propionic acid, 3-(3-methyl­phenyl)­propionic acid and 3-(3-meth­oxy­phenyl)­propionic acid) (Das et al., 2012). The aromatic ring of the title compound is almost coplanar with the C10 methoxyl with which it has a dihedral of less than 0.54 (2) ° while the C11 methoxyl has a corresponding dihedral of just 5.30 (2)°. The angle between the mean planes of the aromatic ring and the propionic acid group (C7, C8, C9, O3 and O4) is 78.56 (2) °. The fully extended propionic side chain is in a trans configuration with (C6—C7—C8—C9) torsion angle of -172.25 (2)°. The O4—H4···O3 hydrogen bonding (Table 1) of the COOH functional groups leads to dimer formation via R22(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 neighboring dimers along [101] direction, the average molecular benzene planes are almost perpendicular to each other, with an angle of 85.33 (2)°. No other appreciable close contacts were noticed except a very weak C3—H3···π inter­action between adjacent dimers along [101], with a bond length of 3.20 (2) Å.

Synthesis and crystallization top

3-(2,5-Di­meth­oxy­phenyl)­propionic acid. - Ethyl 3-(2,5-di­meth­oxy­phenyl)­propionate (3.2 g, 13.4 mmol) in a mixture of aq. NaOH (10 w%, 30 mL) and methanol (8 mL) was heated at reflux for 12h. Then, half. conc. aq. HCl is added to the cooled solution. Thereafter, the mixture is extracted with chloro­form (3 X 15 mL). The organic phase is dried over anhydrous MgSO4 and concentrated in vacuo. The residue is filtered over a small column of silica gel (di­ethyl­ether–CHCl3, 1:1, v/v) to give the title compound (2.56 g, 89%) as colorless needles, mp. 339 – 340 K [Lit. mp. 339-340 K (Anliker et al., 1957)]; νmax (KBr/cm-1) 3500 – 2050 (bs, OH), 2955, 2835, 1699, 1504, 1449, 1430, 1307, 1281, 1182, 1127, 927, 916, 865, 795, 717, 499; δH (400 MHz, CDCl3) 2.65 (2H, t, 3J = 7.6 Hz), 2.91 (2H, t, 3J = 7.6 Hz), 6.71 (1H, dd, 3J = 8.4 Hz, 4J = 3.2 Hz), 6.75 (1H, d, 4J = 3.2 Hz), 6.76 (1H, d, 3J = 8.4 Hz), δC (67.8 MHz, CDCl3) 26.0 (CH2), 33.9 (CH2), 55.6 (OCH3), 55.7 (OCH3), 111.0 (CH), 111.6 (CH), 116.3 (CH), 129.6 (CH), 151.7 (Cquat), 153.3 (Cquat), 179.7 (Cquat, CO).

Refinement top

All hydrogen atoms were placed in calculated positions with C—H distances of 0.95- 0.99 Å and refined as riding with Uiso(H) = xUeq(C), where x = 1.5 for methyl and x = 1.2 for all other H-atoms.

Related literature top

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).

Structure description top

The molecule of the title compound exhibits one conformation (Figure 1), unlike other analogous compounds that exhibit two conformations (e.g. 3-phenyl­propionic acid, 3-(3-methyl­phenyl)­propionic acid and 3-(3-meth­oxy­phenyl)­propionic acid) (Das et al., 2012). The aromatic ring of the title compound is almost coplanar with the C10 methoxyl with which it has a dihedral of less than 0.54 (2) ° while the C11 methoxyl has a corresponding dihedral of just 5.30 (2)°. The angle between the mean planes of the aromatic ring and the propionic acid group (C7, C8, C9, O3 and O4) is 78.56 (2) °. The fully extended propionic side chain is in a trans configuration with (C6—C7—C8—C9) torsion angle of -172.25 (2)°. The O4—H4···O3 hydrogen bonding (Table 1) of the COOH functional groups leads to dimer formation via R22(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 neighboring dimers along [101] direction, the average molecular benzene planes are almost perpendicular to each other, with an angle of 85.33 (2)°. No other appreciable close contacts were noticed except a very weak C3—H3···π inter­action between adjacent dimers along [101], with a bond length of 3.20 (2) Å.

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).

Synthesis and crystallization top

3-(2,5-Di­meth­oxy­phenyl)­propionic acid. - Ethyl 3-(2,5-di­meth­oxy­phenyl)­propionate (3.2 g, 13.4 mmol) in a mixture of aq. NaOH (10 w%, 30 mL) and methanol (8 mL) was heated at reflux for 12h. Then, half. conc. aq. HCl is added to the cooled solution. Thereafter, the mixture is extracted with chloro­form (3 X 15 mL). The organic phase is dried over anhydrous MgSO4 and concentrated in vacuo. The residue is filtered over a small column of silica gel (di­ethyl­ether–CHCl3, 1:1, v/v) to give the title compound (2.56 g, 89%) as colorless needles, mp. 339 – 340 K [Lit. mp. 339-340 K (Anliker et al., 1957)]; νmax (KBr/cm-1) 3500 – 2050 (bs, OH), 2955, 2835, 1699, 1504, 1449, 1430, 1307, 1281, 1182, 1127, 927, 916, 865, 795, 717, 499; δH (400 MHz, CDCl3) 2.65 (2H, t, 3J = 7.6 Hz), 2.91 (2H, t, 3J = 7.6 Hz), 6.71 (1H, dd, 3J = 8.4 Hz, 4J = 3.2 Hz), 6.75 (1H, d, 4J = 3.2 Hz), 6.76 (1H, d, 3J = 8.4 Hz), δC (67.8 MHz, CDCl3) 26.0 (CH2), 33.9 (CH2), 55.6 (OCH3), 55.7 (OCH3), 111.0 (CH), 111.6 (CH), 116.3 (CH), 129.6 (CH), 151.7 (Cquat), 153.3 (Cquat), 179.7 (Cquat, CO).

Refinement details top

All hydrogen atoms were placed in calculated positions with C—H distances of 0.95- 0.99 Å and refined as riding with Uiso(H) = xUeq(C), where x = 1.5 for methyl and x = 1.2 for all other H-atoms.

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); 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).

Figures top
[Figure 1] Fig. 1. A view of title compound molecule with the atom-numbering scheme. Displacement ellipsoids are shown at the 50% probability level.
3-(2,5-Dimethoxyphenyl)propionic acid top
Crystal data top
C11H14O4Dx = 1.324 Mg m−3
Mr = 210.22Melting point = 339–340 K
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 24.3212 (10) ÅCell parameters from 9914 reflections
b = 4.6512 (2) Åθ = 2.3–31.2°
c = 19.7411 (8) ŵ = 0.10 mm−1
β = 109.1782 (6)°T = 100 K
V = 2109.23 (15) Å3Bar, clear light colourless
Z = 80.3 × 0.1 × 0.02 mm
F(000) = 896
Data collection top
Bruker APEXII CCD
diffractometer		2927 reflections with I > 2σ(I)
φ and ω scansRint = 0.028
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		θmax = 31.3°, θmin = 1.8°
Tmin = 0.604, Tmax = 0.746h = −35→34
20284 measured reflectionsk = −6→6
3224 independent reflectionsl = −27→28
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.036H 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 reflectionsΔρmax = 0.44 e Å−3
142 parametersΔρmin = −0.18 e Å−3
0 restraints
Crystal data top
C11H14O4V = 2109.23 (15) Å3
Mr = 210.22Z = 8
Monoclinic, C2/cMo Kα radiation
a = 24.3212 (10) ŵ = 0.10 mm−1
b = 4.6512 (2) ÅT = 100 K
c = 19.7411 (8) Å0.3 × 0.1 × 0.02 mm
β = 109.1782 (6)°
Data collection top
Bruker APEXII CCD
diffractometer		3224 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		2927 reflections with I > 2σ(I)
Tmin = 0.604, Tmax = 0.746Rint = 0.028
20284 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.44 e Å−3
3224 reflectionsΔρmin = −0.18 e Å−3
142 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.36178 (4)0.50978 (18)0.70073 (5)0.01639 (17)
C100.44839 (4)0.3697 (3)0.79439 (5)0.0289 (2)
C110.14931 (4)0.2622 (2)0.61260 (5)0.02223 (19)
C20.32768 (4)0.32755 (19)0.72601 (5)0.01806 (17)
C30.26774 (4)0.30632 (18)0.69042 (5)0.01692 (17)
C40.24216 (4)0.47152 (18)0.62979 (5)0.01575 (16)
C50.27657 (4)0.65750 (18)0.60495 (4)0.01568 (16)
C60.33612 (4)0.67778 (17)0.63904 (4)0.01468 (16)
C70.37340 (4)0.86255 (18)0.60859 (5)0.01664 (16)
C80.39755 (4)0.67941 (18)0.56036 (5)0.01553 (16)
C90.44172 (3)0.82948 (18)0.53467 (4)0.01464 (16)
H10A0.43110.41460.83150.043*
H10B0.49010.41290.81240.043*
H10C0.44270.16530.78200.043*
H11A0.15060.30380.66180.033*
H11B0.16480.06900.61060.033*
H11C0.10900.27240.58030.033*
H20.34520.21620.76790.022*
H30.24470.17960.70770.020*
H40.4791 (8)0.795 (4)0.4682 (10)0.049 (5)*
H50.25870.77240.56380.019*
H7A0.40590.94610.64810.020*
H7B0.34981.02240.58040.020*
H8A0.41560.50460.58710.019*
H8B0.36470.61700.51810.019*
O10.42100 (3)0.53955 (17)0.73202 (4)0.02384 (16)
O20.18373 (3)0.46840 (16)0.59092 (4)0.02300 (16)
O30.46906 (3)1.04245 (15)0.56342 (4)0.02097 (15)
O40.44928 (3)0.70388 (15)0.47828 (4)0.02040 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0167 (4)0.0191 (4)0.0150 (4)0.0013 (3)0.0074 (3)−0.0003 (3)
C100.0211 (4)0.0448 (6)0.0197 (4)0.0072 (4)0.0049 (3)0.0065 (4)
C110.0206 (4)0.0207 (4)0.0263 (4)−0.0063 (3)0.0089 (3)−0.0017 (3)
C20.0221 (4)0.0190 (4)0.0149 (4)0.0013 (3)0.0086 (3)0.0031 (3)
C30.0218 (4)0.0159 (4)0.0162 (4)−0.0015 (3)0.0104 (3)0.0008 (3)
C40.0170 (4)0.0154 (3)0.0162 (4)−0.0009 (3)0.0073 (3)−0.0010 (3)
C50.0196 (4)0.0144 (3)0.0148 (3)0.0004 (3)0.0081 (3)0.0015 (3)
C60.0190 (4)0.0130 (3)0.0155 (4)0.0002 (3)0.0103 (3)−0.0010 (3)
C70.0201 (4)0.0144 (3)0.0200 (4)−0.0012 (3)0.0127 (3)−0.0008 (3)
C80.0166 (4)0.0159 (4)0.0172 (4)−0.0024 (3)0.0099 (3)−0.0016 (3)
C90.0137 (3)0.0159 (4)0.0160 (3)0.0007 (3)0.0072 (3)−0.0003 (3)
O10.0167 (3)0.0334 (4)0.0207 (3)0.0005 (3)0.0053 (2)0.0055 (3)
O20.0176 (3)0.0258 (3)0.0242 (3)−0.0045 (2)0.0049 (3)0.0060 (3)
O30.0239 (3)0.0205 (3)0.0238 (3)−0.0077 (2)0.0150 (3)−0.0069 (2)
O40.0208 (3)0.0229 (3)0.0233 (3)−0.0074 (2)0.0151 (3)−0.0086 (2)
Geometric parameters (Å, º) top
C10—H10C0.9800C6—C51.3854 (12)
C10—H10B0.9800C7—H7B0.9900
C10—H10A0.9800C7—H7A0.9900
C11—H11C0.9800C8—C91.5019 (11)
C11—H11B0.9800C8—C71.5312 (11)
C11—H11A0.9800C8—H8B0.9900
C2—C11.3882 (12)C8—H8A0.9900
C2—H20.9500O1—C101.4299 (12)
C3—C41.3858 (12)O1—C11.3751 (10)
C3—C21.3985 (12)O2—C111.4278 (11)
C3—H30.9500O2—C41.3756 (10)
C5—C41.3995 (11)O3—C91.2238 (10)
C5—H50.9500O4—H40.917 (18)
C6—C11.4085 (12)O4—C91.3224 (10)
C6—C71.5101 (11)
C1—C2—H2119.7C9—C8—H8B108.6
C1—C2—C3120.65 (8)C9—C8—H8A108.6
C1—C6—C7120.43 (8)C9—O4—H4108.5 (11)
C1—O1—C10117.01 (7)H10A—C10—H10C109.5
C2—C1—C6120.15 (8)H10A—C10—H10B109.5
C2—C3—H3120.2H10B—C10—H10C109.5
C3—C4—C5119.66 (8)H11A—C11—H11C109.5
C3—C2—H2119.7H11A—C11—H11B109.5
C4—C5—H5119.3H11B—C11—H11C109.5
C4—C3—C2119.53 (8)H7A—C7—H7B108.2
C4—C3—H3120.2H8A—C8—H8B107.6
C4—O2—C11116.09 (7)O1—C10—H10C109.5
C5—C6—C1118.54 (7)O1—C10—H10B109.5
C5—C6—C7120.93 (7)O1—C10—H10A109.5
C6—C7—H7B109.8O1—C1—C2124.15 (8)
C6—C7—H7A109.8O1—C1—C6115.71 (7)
C6—C7—C8109.52 (7)O2—C11—H11C109.5
C6—C5—C4121.46 (8)O2—C11—H11B109.5
C6—C5—H5119.3O2—C11—H11A109.5
C7—C8—H8B108.6O2—C4—C5115.98 (7)
C7—C8—H8A108.6O2—C4—C3124.36 (8)
C8—C7—H7B109.8O3—C9—C8124.03 (7)
C8—C7—H7A109.8O3—C9—O4122.90 (8)
C9—C8—C7114.48 (7)O4—C9—C8113.05 (7)
C1—C6—C7—C883.52 (9)C5—C6—C1—C20.36 (12)
C1—C6—C5—C4−1.12 (12)C5—C6—C1—O1179.97 (7)
C10—O1—C1—C20.15 (13)C5—C6—C7—C8−92.96 (9)
C10—O1—C1—C6−179.45 (8)C6—C5—C4—C30.97 (13)
C11—O2—C4—C5175.08 (8)C6—C5—C4—O2−179.31 (7)
C11—O2—C4—C3−5.21 (13)C7—C8—C9—O319.85 (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—C60.56 (13)C7—C6—C1—O13.41 (11)
C3—C2—C1—O1−179.02 (8)C7—C6—C5—C4175.42 (7)
C4—C3—C2—C1−0.73 (13)C9—C8—C7—C6−172.25 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O3i0.92 (2)1.75 (2)2.6624 (11)172.1 (18)
Symmetry code: (i) −x+1, −y+2, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O3i0.92 (2)1.75 (2)2.6624 (11)172.1 (18)
Symmetry code: (i) −x+1, −y+2, −z+1.
 

Acknowledgements

MA thanks the UAEU for a PhD scholarship.

References

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ISSN: 2056-9890
Volume 71| Part 5| May 2015| Pages o337-o338
https://doi.org/10.1107/S2056989015007641
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