Methyl 4-benz-yloxy-2-hy-droxy-benzoate.

In the title compound, C15H14O4, the dihedral angle between the benzene rings is 67.18 (8)°. The Ca-Cm-O-Ca (a = aromatic and m = methyl-ene) torsion angle is 172.6 (3)° and an intra-molecular O-H⋯O hydrogen bond generates an S(6) ring. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds into zigzag chains propagating in [001] and C-H⋯π inter-actions also occur.

Related literature

For general background to benzyl­oxybenzoates, see: Pifferi et al. (1977 ▶); Ghosh et al. (2008 ▶). For related structures and further synthetic details, see: Tangdenpaisal et al. (2009 ▶); Kashi et al. (2010 ▶).

Experimental

Crystal data

C15H14O4

M = 258.26

Triclinic,

a = 5.7731 (10) Å

b = 7.9855 (14) Å

c = 14.046 (3) Å

α = 89.490 (6)°

β = 80.111 (5)°

γ = 87.210 (6)°

V = 637.16 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.24 × 0.22 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.977, T max = 0.983

12770 measured reflections

2231 independent reflections

1679 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.129

S = 1.07

2231 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 (Farrugia, 2012) ▶; software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812046491/hb6982sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046491/hb6982Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046491/hb6982Isup3.cml

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

C15H14O4	Z = 2
Mr = 258.26	F(000) = 272
Triclinic, P1	Dx = 1.346 Mg m−3
Hall symbol: -P 1	Melting point: 377 K
a = 5.7731 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.9855 (14) Å	Cell parameters from 2231 reflections
c = 14.046 (3) Å	θ = 2.6–25.0°
α = 89.490 (6)°	µ = 0.10 mm−1
β = 80.111 (5)°	T = 293 K
γ = 87.210 (6)°	Plate, colourless
V = 637.16 (19) Å3	0.24 × 0.22 × 0.18 mm

Bruker SMART CCD diffractometer	2231 independent reflections
Radiation source: fine-focus sealed tube	1679 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
ω and φ scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −6→6
Tmin = 0.977, Tmax = 0.983	k = −9→9
12770 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.129	w = 1/[σ2(Fo2) + (0.0713P)2 + 0.0386P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2231 reflections	Δρmax = 0.17 e Å−3
173 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.069 (9)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.3228 (2)	0.20059 (14)	0.10019 (7)	0.0518 (4)
O2	0.1364 (2)	0.41392 (14)	0.42117 (8)	0.0574 (4)
H2	0.1856	0.4109	0.4726	0.086*
O3	0.4189 (2)	0.31994 (16)	0.54049 (8)	0.0605 (4)
O4	0.7269 (2)	0.14432 (15)	0.48726 (8)	0.0568 (4)
C5	−0.0453 (3)	0.2119 (2)	−0.06754 (12)	0.0516 (5)
H5	−0.1633	0.1609	−0.0253	0.062*
C6	−0.0486 (3)	0.2107 (2)	−0.16596 (12)	0.0579 (5)
H6	−0.1693	0.1600	−0.1893	0.069*
C7	0.1252 (3)	0.2840 (2)	−0.22893 (12)	0.0563 (5)
H7	0.1224	0.2838	−0.2949	0.068*
C8	0.3032 (3)	0.3575 (2)	−0.19423 (12)	0.0578 (5)
H8	0.4226	0.4063	−0.2368	0.069*
C9	0.3056 (3)	0.3594 (2)	−0.09595 (12)	0.0549 (5)
H9	0.4271	0.4097	−0.0730	0.066*
C10	0.1305 (3)	0.2876 (2)	−0.03155 (11)	0.0443 (4)
C11	0.1266 (3)	0.2994 (2)	0.07531 (11)	0.0534 (5)
H11A	0.1366	0.4154	0.0935	0.064*
H11B	−0.0197	0.2585	0.1101	0.064*
C12	0.3616 (3)	0.21291 (19)	0.19290 (10)	0.0406 (4)
C13	0.5597 (3)	0.1217 (2)	0.21350 (11)	0.0477 (4)
H13	0.6521	0.0552	0.1662	0.057*
C14	0.6165 (3)	0.1310 (2)	0.30389 (11)	0.0471 (4)
H14	0.7493	0.0707	0.3171	0.057*
C15	0.4801 (3)	0.22901 (18)	0.37723 (10)	0.0400 (4)
C16	0.2802 (3)	0.31707 (18)	0.35554 (11)	0.0406 (4)
C17	0.2211 (3)	0.30868 (19)	0.26383 (11)	0.0433 (4)
H17	0.0875	0.3674	0.2503	0.052*
C18	0.5349 (3)	0.23696 (19)	0.47507 (11)	0.0444 (4)
C19	0.7991 (4)	0.1564 (2)	0.58079 (13)	0.0637 (5)
H19A	0.9378	0.0855	0.5817	0.096*
H19B	0.6749	0.1213	0.6303	0.096*
H19C	0.8323	0.2704	0.5922	0.096*

	U11	U22	U33	U12	U13	U23
O1	0.0604 (7)	0.0624 (7)	0.0333 (6)	0.0172 (6)	−0.0155 (5)	−0.0058 (5)
O2	0.0632 (8)	0.0671 (8)	0.0402 (7)	0.0173 (6)	−0.0085 (6)	−0.0148 (5)
O3	0.0718 (9)	0.0731 (8)	0.0362 (7)	0.0062 (7)	−0.0110 (6)	−0.0084 (6)
O4	0.0628 (8)	0.0695 (8)	0.0423 (7)	0.0048 (6)	−0.0230 (6)	−0.0020 (6)
C5	0.0496 (10)	0.0602 (10)	0.0461 (10)	−0.0027 (8)	−0.0109 (8)	0.0012 (8)
C6	0.0567 (11)	0.0682 (12)	0.0534 (11)	0.0005 (9)	−0.0229 (9)	−0.0096 (9)
C7	0.0670 (12)	0.0686 (11)	0.0345 (9)	0.0143 (9)	−0.0164 (8)	−0.0038 (8)
C8	0.0580 (11)	0.0699 (12)	0.0427 (10)	−0.0022 (9)	−0.0012 (8)	0.0039 (8)
C9	0.0491 (10)	0.0693 (12)	0.0484 (10)	−0.0070 (9)	−0.0130 (8)	−0.0057 (8)
C10	0.0454 (9)	0.0522 (9)	0.0358 (8)	0.0082 (7)	−0.0114 (7)	−0.0019 (7)
C11	0.0523 (10)	0.0702 (11)	0.0378 (9)	0.0136 (8)	−0.0127 (8)	−0.0024 (8)
C12	0.0471 (9)	0.0443 (9)	0.0312 (8)	0.0008 (7)	−0.0095 (7)	−0.0004 (6)
C13	0.0510 (10)	0.0563 (10)	0.0340 (8)	0.0119 (8)	−0.0060 (7)	−0.0059 (7)
C14	0.0457 (9)	0.0555 (10)	0.0401 (9)	0.0090 (8)	−0.0102 (7)	0.0008 (7)
C15	0.0446 (9)	0.0425 (8)	0.0333 (8)	−0.0026 (7)	−0.0077 (7)	0.0009 (6)
C16	0.0464 (9)	0.0393 (8)	0.0346 (8)	0.0000 (7)	−0.0035 (7)	−0.0026 (6)
C17	0.0452 (9)	0.0459 (9)	0.0396 (9)	0.0057 (7)	−0.0115 (7)	−0.0001 (7)
C18	0.0507 (10)	0.0461 (9)	0.0377 (9)	−0.0071 (8)	−0.0094 (7)	0.0026 (7)
C19	0.0778 (13)	0.0748 (12)	0.0459 (10)	−0.0062 (10)	−0.0311 (9)	0.0036 (9)

O1—C12	1.3638 (17)	C9—H9	0.9300
O1—C11	1.4393 (19)	C10—C11	1.501 (2)
O2—C16	1.3509 (18)	C11—H11A	0.9700
O2—H2	0.8200	C11—H11B	0.9700
O3—C18	1.2198 (19)	C12—C17	1.382 (2)
O4—C18	1.337 (2)	C12—C13	1.397 (2)
O4—C19	1.4502 (19)	C13—C14	1.368 (2)
C5—C10	1.376 (2)	C13—H13	0.9300
C5—C6	1.386 (2)	C14—C15	1.403 (2)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.369 (3)	C15—C16	1.399 (2)
C6—H6	0.9300	C15—C18	1.465 (2)
C7—C8	1.369 (3)	C16—C17	1.391 (2)
C7—H7	0.9300	C17—H17	0.9300
C8—C9	1.383 (2)	C19—H19A	0.9600
C8—H8	0.9300	C19—H19B	0.9600
C9—C10	1.379 (2)	C19—H19C	0.9600
C12—O1—C11	116.82 (12)	O1—C12—C17	124.30 (14)
C16—O2—H2	109.5	O1—C12—C13	115.41 (14)
C18—O4—C19	116.31 (14)	C17—C12—C13	120.29 (14)
C10—C5—C6	120.76 (17)	C14—C13—C12	119.41 (15)
C10—C5—H5	119.6	C14—C13—H13	120.3
C6—C5—H5	119.6	C12—C13—H13	120.3
C7—C6—C5	120.18 (16)	C13—C14—C15	121.85 (15)
C7—C6—H6	119.9	C13—C14—H14	119.1
C5—C6—H6	119.9	C15—C14—H14	119.1
C8—C7—C6	119.67 (16)	C16—C15—C14	117.79 (14)
C8—C7—H7	120.2	C16—C15—C18	119.60 (14)
C6—C7—H7	120.2	C14—C15—C18	122.57 (14)
C7—C8—C9	120.09 (17)	O2—C16—C17	116.75 (14)
C7—C8—H8	120.0	O2—C16—C15	122.45 (14)
C9—C8—H8	120.0	C17—C16—C15	120.81 (14)
C10—C9—C8	120.92 (16)	C12—C17—C16	119.83 (14)
C10—C9—H9	119.5	C12—C17—H17	120.1
C8—C9—H9	119.5	C16—C17—H17	120.1
C5—C10—C9	118.37 (15)	O3—C18—O4	122.01 (14)
C5—C10—C11	121.05 (16)	O3—C18—C15	124.12 (15)
C9—C10—C11	120.52 (15)	O4—C18—C15	113.87 (14)
O1—C11—C10	109.23 (13)	O4—C19—H19A	109.5
O1—C11—H11A	109.8	O4—C19—H19B	109.5
C10—C11—H11A	109.8	H19A—C19—H19B	109.5
O1—C11—H11B	109.8	O4—C19—H19C	109.5
C10—C11—H11B	109.8	H19A—C19—H19C	109.5
H11A—C11—H11B	108.3	H19B—C19—H19C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.82	1.89	2.6133 (17)	146
C19—H19C···O2i	0.96	2.54	3.469 (3)	163
C11—H11A···Cg1ii	0.97	2.78	3.5991 (19)	143
C13—H13···Cg1iii	0.93	2.95	3.7324 (19)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.82	1.89	2.6133 (17)	146
C19—H19C⋯O2i	0.96	2.54	3.469 (3)	163
C11—H11A⋯Cg1ii	0.97	2.78	3.5991 (19)	143
C13—H13⋯Cg1iii	0.93	2.95	3.7324 (19)	142

Symmetry codes: (i) ; (ii) ; (iii) .