Methyl 3-(4-hy­droxy­phen­yl)propionate

Abdou, M.M.; Matziari, M.; O'Neill, P.M.; Amigues, E.; Zhou, R.; Wang, R.; Ali, B.F.

doi:10.1107/S2414314618016620

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 11| November 2018| x181662

https://doi.org/10.1107/S2414314618016620

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Methyl 3-(4-hydroxyphenyl)propionate

Moaz M. Abdou,^a,^b,^c Magdalini Matziari,^b ^* Paul M. O'Neill,^c,^d Eric Amigues,^b Ruixue Zhou,^b Ruiyao Wang ^b and Basem F. Ali ^e

^aEgyptian Petroleum Research Institute, Nasr City, PO 11727, Cairo, Egypt, ^bDepartment of Chemistry, Xi'an Jiaotong Liverpool University, Suzhou, Jiangsu, 215123, People's Republic of China, ^cDepartment of Chemistry, University of Liverpool, Liverpool L69 7ZD, UK, ^dDepartment of Pharmacology, School of Biomedical Sciences, MRC Centre for Drug Safety Science, University of Liverpool, Liverpool L69 3GE, UK, and ^eDepartment of Chemistry, Al al-Bayt University, Mafraq 25113, Jordan
^*Correspondence e-mail: magdalini.matziari@xjtlu.edu.cn

Edited by C. Rizzoli, Universita degli Studi di Parma, Italy (Received 29 October 2018; accepted 22 November 2018; online 27 November 2018)

The title compound, C₁₀H₁₂O₃, crystallizes in the orthorhombic P2₁2₁2₁ space group. The structure contains a phenolic group with the OH being coplanar with the phenyl ring. The structure exhibits significant hydrogen bonding between the O—H group of one molecule and the CO group of an adjacent one. These O—H⋯O=C interactions form chains of molecules parallel to the b axis. No π–π or C—H⋯π intermolecular interactions are observed.

Keywords: crystal structure; nitrification inhibitor; phenolic compounds; hydrogen bonding.

CCDC reference: 1880603

Structure description

The application of nitrogen-based fertilizers has been a remarkable strategy applied to meet the growing world food and fibre demands over the past 80 years (Galloway et al., 2008 ). However, these fertilizers increase anthropogenic nitrous oxide production, causing serious effects on the environment in water, the air and soil. One of the important environmentally friendly techniques applied in agriculture to control the rate of the climate-relevant N₂O gas emission is the use of nitrification inhibitors (Ruser & Schulz, 2015 ). Among the various nitrification inhibitors, methyl 3-(2 or 4-hydroxyphenyl)propionates (MHPPs) are the most important formed in sorghum (Sorghum bicolor; Zakir et al., 2008 ; Nardi et al., 2013 ). Additionally, they exhibit an interesting motif in the enzymatic coupling of saccharides to proteins, also acting as modulators of the root system architecture (RSA; Martinez et al., 2017 ; ter Haar et al., 2011 ). There are various reports on the synthesis of methyl 3-(2-hydroxyphenyl)propionate (Yuthavong et al., 2012 ; Rosales et al., 2011 ; Meier et al., 2006 ), but its crystal structure has not previously been been reported. As part of our ongoing studies on the synthesis and properties of phenolic compounds (Abdou, 2013a ,b , 2017a ,b ,c , 2018 ; Abdou et al., 2012a ,b ,c , 2013 , 2015 , 2015a ,b , 2016 ; Abdou et al., 2015a,b; Abdou, El-Saeed, Abozeid et al., 2015; Metwally et al., 2012a ,b , 2013 ), we report herein the crystal structure of methyl 3-(2-hydroxyphenyl)propionate.

The molecular structure of the title compound is depicted in Fig. 1. The phenyl ring is planar with the hydroxyl group being coplanar with a C2—C1—O1—H1H torsion angle of −8 (2)°. The bond distances and angles within the phenolic ring, the propionate group and the co-planarity of OH group with the phenyl ring are consistent with related structures such as methyl 3-(3,5-di-tertbutyl-4-hydroxyphenyl)propionate (Li et al., 2014 ), 2-(4-acetylanilino)-2-oxoethyl 3-(4-hydroxyphenyl)propionate (Ashraf et al., 2016 ) and methyl 3-[3-tert-butyl-5-(6-chloro-1-oxybenzotriazol-2-yl)-4-hydroxyphenyl]propionate (Wen et al., 2006 ).

Figure 1
The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

The crystal structure exhibits significant hydrogen-bonding interactions (Table 1), in which the O1—H1 groups acts as the donor while the carbonyl group of an adjacent molecule (–x + 1, y + $[{1\over 2}]$ , –z + $[{3\over 2}]$ ) being the acceptor. These hydrogen bonds shown as dashed lines in Fig. 2) connect the molecules into chains running parallel to the b axis (Fig. 3). π–π stacking and C—H⋯π interactions are not present in the crystal structure.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1H⋯O2ⁱ	0.86 (3)	1.96 (4)	2.805 (3)	169 (3)
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 2
Hydrogen-bonding interactions (dashed lines) between adjacent molecules. Symmetry codes: (i) −x + 1, y + $[{1\over 2}]$ , −z + $[{3\over 2}]$ ; (ii) −x + 1, y − $[{1\over 2}]$ , −z + $[{3\over 2}]$ .

Figure 3
Crystal packing of the title compound viewed along the a axis, showing the chains parallel to the a axis formed via hydrogen bonding (dashed lines).

Synthesis and crystallization

A mixture of dihydrocoumarin (1 ml, 7.89 mmol), a catalytic amount of conc. H₂SO₄, and 30 ml of dry MeOH were heated under reflux for 5 h. The methanol was removed in vacuo and the residue was neutralized with saturated NaHCO₃ solution then diluted with water and extracted with Et₂O. The combined organic extracts were dried over MgSO₄, filtered and concentrated. The crude compound was crystallized by slow evaporation of a diethyl ether–hexane mixture (2:1 v/v) to give colourless single crystals (1.22 g, 86%). M.p. 41–42°C; IR (KBr, cm⁻¹) 3420, 3055, 1735, 1447. ¹H NMR (400 MHz, CDCl₃) δ 2.76 (t, J = 6.6 Hz, 3H), 2.95 (t, J = 6.6 Hz, 2H), 3.72 (s, 3H), 6.89 (d, J = 7.4 Hz, 2H), 7.12–7.16 (m, 2H). ¹³C NMR (100 MHz, DMSO-d₆) δ 24.86, 34.87, 52.24, 116.82, 120.81, 127.07, 128.23, 130.52, 154.26, 175.96. HRMS (ESI/QTOF) m/z: [M]⁺ calculated for C₁₀H₁₂O₃ 180.0786, found 180.0774.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₀H₁₂O₃
M_r	180.20
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	180
a, b, c (Å)	5.4774 (6), 11.1557 (12), 14.5610 (17)
V (Å³)	889.74 (17)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.35 × 0.15 × 0.10

Data collection
Diffractometer	Bruker D8 Venture diffractometer with PHOTON 100 CMOS detecter
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.614, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	9443, 1756, 1390
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.091, 1.04
No. of reflections	1756
No. of parameters	122
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.15
Absolute structure	Flack x determined using 467 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	−0.5 (8)
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXS97 and SHELXTL (Sheldrick, 2008 ) and SHELXL2018 (Sheldrick, 2015 ).

Structural data

CCDC reference: 1880603

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314618016620/rz4027sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618016620/rz4027Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618016620/rz4027Isup3.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Methyl 3-(4-hydroxyphenyl)propionate top

Crystal data top

C₁₀H₁₂O₃	D_x = 1.345 Mg m⁻³
M_r = 180.20	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 2736 reflections
a = 5.4774 (6) Å	θ = 3.3–27.6°
b = 11.1557 (12) Å	µ = 0.10 mm⁻¹
c = 14.5610 (17) Å	T = 180 K
V = 889.74 (17) Å³	Block, colourless
Z = 4	0.35 × 0.15 × 0.10 mm
F(000) = 384

Data collection top

Bruker D8 Venture diffractometer with PHOTON 100 CMOS detecter	1390 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.056
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θ_max = 26.0°, θ_min = 3.3°
T_min = 0.614, T_max = 0.746	h = −6→6
9443 measured reflections	k = −13→13
1756 independent reflections	l = −17→17

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.040	w = 1/[σ²(F_o²) + (0.0427P)² + 0.1279P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.091	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.19 e Å⁻³
1756 reflections	Δρ_min = −0.15 e Å⁻³
122 parameters	Absolute structure: Flack x determined using 467 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: −0.5 (8)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. All hydrogen atoms on carbon atoms were calculated with C–H = 0.95, 0.98 and 0.99 Å for CH (aromatic), CH₂ and CH₃, respectively, and refined as riding atoms with U_iso(H) = 1.2 U_eq(C) for CH (aromatic) and CH₂, and 1.5 U_eq(C) for CH₃. The H atoms of the –OH group was located in a differenceFourier map and refined without any constraint.

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

	x	y	z	U_iso*/U_eq
O1	0.5468 (3)	0.18977 (17)	0.77139 (13)	0.0302 (5)
H1H	0.642 (6)	0.235 (3)	0.740 (2)	0.051 (11)*
O2	0.1249 (3)	−0.19195 (17)	0.84546 (13)	0.0304 (5)
O3	−0.2348 (3)	−0.18421 (16)	0.91771 (11)	0.0267 (5)
C1	0.3762 (5)	0.2573 (2)	0.81696 (17)	0.0220 (6)
C2	0.3865 (5)	0.3815 (2)	0.8200 (2)	0.0270 (7)
H2A	0.515418	0.422762	0.789969	0.032*
C3	0.2091 (5)	0.4451 (2)	0.86675 (19)	0.0293 (7)
H3A	0.215294	0.530216	0.868476	0.035*
C4	0.0235 (6)	0.3849 (2)	0.9108 (2)	0.0293 (7)
H4A	−0.097370	0.428212	0.943778	0.035*
C5	0.0136 (5)	0.2607 (2)	0.90690 (18)	0.0248 (6)
H5A	−0.115233	0.219904	0.937426	0.030*
C6	0.1866 (4)	0.1949 (2)	0.85970 (16)	0.0203 (6)
C7	0.1802 (5)	0.0596 (2)	0.85041 (19)	0.0251 (6)
H7A	0.191282	0.038987	0.784403	0.030*
H7B	0.326584	0.026163	0.881019	0.030*
C8	−0.0424 (5)	−0.0006 (2)	0.88985 (19)	0.0226 (6)
H8A	−0.055581	0.020109	0.955777	0.027*
H8B	−0.189442	0.030922	0.858512	0.027*
C9	−0.0375 (5)	−0.1341 (2)	0.88018 (19)	0.0209 (6)
C10	−0.2421 (5)	−0.3137 (2)	0.91727 (19)	0.0304 (7)
H10A	−0.393610	−0.341096	0.946253	0.046*
H10B	−0.235700	−0.342708	0.853791	0.046*
H10C	−0.101883	−0.345081	0.951474	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0222 (10)	0.0322 (11)	0.0363 (12)	−0.0049 (10)	0.0094 (9)	0.0037 (10)
O2	0.0278 (11)	0.0272 (10)	0.0362 (11)	0.0043 (9)	0.0102 (8)	−0.0033 (10)
O3	0.0245 (10)	0.0204 (9)	0.0353 (11)	−0.0020 (9)	0.0084 (8)	−0.0006 (9)
C1	0.0193 (16)	0.0266 (15)	0.0201 (14)	−0.0011 (12)	−0.0020 (12)	0.0008 (12)
C2	0.0226 (17)	0.0289 (16)	0.0296 (18)	−0.0085 (12)	−0.0028 (14)	0.0050 (12)
C3	0.0329 (16)	0.0195 (14)	0.0355 (17)	−0.0050 (13)	−0.0071 (14)	0.0006 (13)
C4	0.0290 (18)	0.0259 (16)	0.0329 (18)	0.0021 (13)	−0.0005 (15)	−0.0045 (12)
C5	0.0203 (16)	0.0265 (15)	0.0276 (16)	−0.0018 (12)	0.0029 (13)	0.0009 (12)
C6	0.0190 (13)	0.0213 (13)	0.0206 (14)	−0.0018 (12)	−0.0030 (11)	0.0018 (12)
C7	0.0226 (14)	0.0248 (15)	0.0278 (15)	0.0000 (12)	0.0048 (13)	0.0015 (13)
C8	0.0204 (14)	0.0223 (13)	0.0251 (14)	0.0015 (11)	0.0034 (12)	0.0013 (12)
C9	0.0200 (14)	0.0239 (14)	0.0188 (14)	0.0001 (12)	0.0016 (12)	0.0019 (11)
C10	0.0365 (16)	0.0195 (14)	0.0353 (16)	−0.0042 (14)	0.0031 (13)	0.0001 (13)

Geometric parameters (Å, º) top

O1—C1	1.372 (3)	C5—C6	1.381 (4)
O1—H1H	0.86 (3)	C5—H5A	0.9500
O2—C9	1.210 (3)	C6—C7	1.516 (4)
O3—C9	1.334 (3)	C7—C8	1.506 (3)
O3—C10	1.445 (3)	C7—H7A	0.9900
C1—C2	1.387 (3)	C7—H7B	0.9900
C1—C6	1.397 (4)	C8—C9	1.496 (3)
C2—C3	1.382 (4)	C8—H8A	0.9900
C2—H2A	0.9500	C8—H8B	0.9900
C3—C4	1.377 (4)	C10—H10A	0.9800
C3—H3A	0.9500	C10—H10B	0.9800
C4—C5	1.388 (4)	C10—H10C	0.9800
C4—H4A	0.9500

C1—O1—H1H	111 (2)	C8—C7—H7A	108.4
C9—O3—C10	116.1 (2)	C6—C7—H7A	108.4
O1—C1—C2	122.4 (3)	C8—C7—H7B	108.4
O1—C1—C6	116.6 (2)	C6—C7—H7B	108.4
C2—C1—C6	120.9 (3)	H7A—C7—H7B	107.5
C3—C2—C1	120.0 (3)	C9—C8—C7	113.2 (2)
C3—C2—H2A	120.0	C9—C8—H8A	108.9
C1—C2—H2A	120.0	C7—C8—H8A	108.9
C4—C3—C2	119.8 (3)	C9—C8—H8B	108.9
C4—C3—H3A	120.1	C7—C8—H8B	108.9
C2—C3—H3A	120.1	H8A—C8—H8B	107.8
C3—C4—C5	119.8 (3)	O2—C9—O3	122.9 (2)
C3—C4—H4A	120.1	O2—C9—C8	125.7 (2)
C5—C4—H4A	120.1	O3—C9—C8	111.4 (2)
C6—C5—C4	121.6 (3)	O3—C10—H10A	109.5
C6—C5—H5A	119.2	O3—C10—H10B	109.5
C4—C5—H5A	119.2	H10A—C10—H10B	109.5
C5—C6—C1	117.8 (2)	O3—C10—H10C	109.5
C5—C6—C7	123.9 (2)	H10A—C10—H10C	109.5
C1—C6—C7	118.3 (2)	H10B—C10—H10C	109.5
C8—C7—C6	115.4 (2)

O1—C1—C2—C3	179.8 (2)	O1—C1—C6—C7	−1.6 (3)
C6—C1—C2—C3	0.8 (4)	C2—C1—C6—C7	177.5 (2)
C1—C2—C3—C4	0.5 (4)	C5—C6—C7—C8	5.0 (4)
C2—C3—C4—C5	−0.9 (4)	C1—C6—C7—C8	−174.0 (2)
C3—C4—C5—C6	0.1 (5)	C6—C7—C8—C9	−179.1 (2)
C4—C5—C6—C1	1.2 (4)	C10—O3—C9—O2	1.8 (4)
C4—C5—C6—C7	−177.9 (3)	C10—O3—C9—C8	−176.4 (2)
O1—C1—C6—C5	179.3 (2)	C7—C8—C9—O2	0.5 (4)
C2—C1—C6—C5	−1.6 (4)	C7—C8—C9—O3	178.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1H···O2ⁱ	0.86 (3)	1.96 (4)	2.805 (3)	169 (3)

Symmetry code: (i) −x+1, y+1/2, −z+3/2.

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