Dimethyl 5,5'-methyl-enebis(2-hy-droxy-benzoate).

In the title compound, C(17)H(16)O(6), the two methyl salicylate moieties are related by crystallographic twofold rotational symmetry with the two benzene rings close to being perpendicular [inter-ring dihedral angle = 86.6 (8)°]. Intra-molecular phenolic O-H⋯O hydrogen bonds with carboxyl O-atom acceptors are present, with these groups also involved in centrosymmetric cyclic inter-molecular O-H⋯O hydrogen-bonding associations [graph set R(2) (2)(4)], giving infinite chains extending across (101).

Related literature

For the chemistry and applications of methyl­ene bis­phenol derivatives, see: Ogata et al. (1975 ▶); Méric et al. (1993 ▶); Shrestha et al. (2007 ▶); Cameron et al. (2002 ▶). For the preparation, see: Cushman & Kanamathareddy (1990 ▶); Méric et al. (1993 ▶). For the structures of similar compounds, see: Lu et al. (2011 ▶); Zhang et al. (2009 ▶); Liu et al. (2009 ▶). For graph-set analysis, see Etter et al. (1990 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H16O6

M = 316.31

Monoclinic,

a = 20.4168 (13) Å

b = 4.9300 (3) Å

c = 15.5470 (12) Å

β = 111.290 (3)°

V = 1458.08 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 150 K

0.38 × 0.30 × 0.24 mm

Data collection

Bruker SMART CCD-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.953, T max = 0.970

8440 measured reflections

1756 independent reflections

1568 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.113

S = 0.96

1756 reflections

109 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.33 e Å−3

Data collection: SMART (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812015760/zs2198sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015760/zs2198Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812015760/zs2198Isup3.cml

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

C17H16O6	F(000) = 664
Mr = 316.31	Dx = 1.441 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8440 reflections
a = 20.4168 (13) Å	θ = 2.8–27.9°
b = 4.9300 (3) Å	µ = 0.11 mm−1
c = 15.5470 (12) Å	T = 150 K
β = 111.290 (3)°	Block, colourless
V = 1458.08 (17) Å3	0.38 × 0.30 × 0.24 mm
Z = 4

Bruker SMART CCD-detector diffractometer	1756 independent reflections
Radiation source: fine-focus sealed tube	1568 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω and φ scans	θmax = 27.9°, θmin = 4.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −26→21
Tmin = 0.953, Tmax = 0.970	k = −6→6
8440 measured reflections	l = −19→20

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ2(Fo2) + (0.0724P)2 + 0.9516P] where P = (Fo2 + 2Fc2)/3
1756 reflections	(Δ/σ)max = 0.049
109 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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	Occ. (<1)
H1	0.2434 (10)	1.009 (5)	0.9251 (15)	0.070 (6)*
O2	0.18996 (4)	1.12860 (16)	0.99304 (5)	0.0260 (2)
O1	0.24736 (4)	0.89366 (17)	0.88455 (6)	0.0265 (2)
O3	0.08604 (4)	0.98089 (17)	0.99095 (6)	0.0284 (2)
C5	0.07384 (5)	0.6081 (2)	0.85532 (7)	0.0212 (2)
H5	0.0372	0.6288	0.8789	0.025*
C6	0.13366 (5)	0.7717 (2)	0.89054 (7)	0.0189 (2)
C2	0.18118 (6)	0.5483 (2)	0.78810 (8)	0.0269 (3)
H2	0.2178	0.5240	0.7648	0.032*
C7	0.14042 (5)	0.9762 (2)	0.96221 (7)	0.0196 (2)
C3	0.12105 (6)	0.3904 (2)	0.75449 (8)	0.0277 (3)
H3	0.1170	0.2602	0.7078	0.033*
C1	0.18813 (5)	0.7425 (2)	0.85599 (7)	0.0212 (2)
C4	0.06631 (5)	0.4174 (2)	0.78730 (7)	0.0238 (2)
C9	0.0000	0.2479 (3)	0.7500	0.0296 (4)
H9A	−0.0029	0.1295	0.7999	0.036*	0.50
H9B	0.0029	0.1295	0.7001	0.036*	0.50
C8	0.09263 (7)	1.1785 (3)	1.06230 (9)	0.0350 (3)
H8A	0.0510	1.1700	1.0796	0.053*
H8B	0.0966	1.3604	1.0393	0.053*
H8C	0.1347	1.1389	1.1165	0.053*

	U11	U22	U33	U12	U13	U23
O2	0.0226 (4)	0.0255 (4)	0.0290 (4)	−0.0081 (3)	0.0084 (3)	−0.0051 (3)
O1	0.0221 (4)	0.0265 (4)	0.0335 (5)	−0.0035 (3)	0.0132 (3)	−0.0013 (3)
O3	0.0247 (4)	0.0324 (5)	0.0315 (4)	−0.0085 (3)	0.0142 (3)	−0.0101 (3)
C5	0.0180 (4)	0.0180 (5)	0.0235 (5)	0.0006 (4)	0.0027 (4)	0.0024 (4)
C6	0.0178 (4)	0.0171 (5)	0.0188 (5)	0.0007 (3)	0.0031 (4)	0.0023 (4)
C2	0.0289 (5)	0.0259 (5)	0.0266 (5)	0.0049 (4)	0.0110 (4)	0.0009 (4)
C7	0.0175 (4)	0.0200 (5)	0.0191 (5)	−0.0013 (3)	0.0043 (4)	0.0025 (4)
C3	0.0335 (6)	0.0207 (5)	0.0235 (5)	0.0050 (4)	0.0039 (4)	−0.0024 (4)
C1	0.0200 (5)	0.0199 (5)	0.0218 (5)	0.0014 (4)	0.0052 (4)	0.0045 (4)
C4	0.0227 (5)	0.0157 (5)	0.0242 (5)	0.0020 (4)	−0.0021 (4)	0.0026 (4)
C9	0.0247 (7)	0.0162 (7)	0.0350 (8)	0.000	−0.0045 (6)	0.000
C8	0.0396 (7)	0.0382 (7)	0.0338 (6)	−0.0085 (5)	0.0211 (5)	−0.0124 (5)

O2—C7	1.2104 (13)	C2—C1	1.3938 (15)
O1—C1	1.3508 (13)	C2—H2	0.9500
O1—H1	0.87 (2)	C3—C4	1.3932 (17)
O3—C7	1.3390 (12)	C3—H3	0.9500
O3—C8	1.4455 (14)	C4—C9	1.5157 (13)
C5—C4	1.3811 (15)	C9—C4i	1.5157 (13)
C5—C6	1.3989 (14)	C9—H9A	0.9900
C5—H5	0.9500	C9—H9B	0.9900
C6—C1	1.4071 (14)	C8—H8A	0.9800
C6—C7	1.4715 (14)	C8—H8B	0.9800
C2—C3	1.3857 (16)	C8—H8C	0.9800
C1—O1—H1	106.9 (13)	O1—C1—C6	123.74 (10)
C7—O3—C8	114.23 (8)	C2—C1—C6	118.82 (10)
C4—C5—C6	122.07 (10)	C5—C4—C3	117.65 (10)
C4—C5—H5	119.0	C5—C4—C9	120.26 (10)
C6—C5—H5	119.0	C3—C4—C9	122.08 (9)
C5—C6—C1	119.36 (9)	C4—C9—C4i	113.07 (12)
C5—C6—C7	121.34 (9)	C4—C9—H9A	109.0
C1—C6—C7	119.30 (9)	C4i—C9—H9A	109.0
C3—C2—C1	120.27 (10)	C4—C9—H9B	109.0
C3—C2—H2	119.9	C4i—C9—H9B	109.0
C1—C2—H2	119.9	H9A—C9—H9B	107.8
O2—C7—O3	122.15 (9)	O3—C8—H8A	109.5
O2—C7—C6	124.07 (9)	O3—C8—H8B	109.5
O3—C7—C6	113.78 (8)	H8A—C8—H8B	109.5
C2—C3—C4	121.81 (10)	O3—C8—H8C	109.5
C2—C3—H3	119.1	H8A—C8—H8C	109.5
C4—C3—H3	119.1	H8B—C8—H8C	109.5
O1—C1—C2	117.44 (9)
C8—O3—C7—O2	−1.07 (15)	C3—C4—C5—C6	0.43 (15)
C8—O3—C7—C6	179.17 (9)	C9—C4—C5—C6	−178.93 (9)
O1—C1—C2—C3	−178.69 (10)	C3—C4—C9—C4i	−123.32 (10)
C6—C1—C2—C3	1.01 (16)	C5—C4—C9—C4i	56.01 (11)
O1—C1—C6—C5	178.95 (10)	C4—C5—C6—C1	0.00 (16)
O1—C1—C6—C7	−0.29 (15)	C4—C5—C6—C7	179.24 (10)
C2—C1—C6—C5	−0.73 (15)	C1—C6—C7—O2	1.60 (16)
C2—C1—C6—C7	−179.97 (10)	C1—C6—C7—O3	−178.64 (9)
C1—C2—C3—C4	−0.58 (17)	C5—C6—C7—O2	−177.63 (10)
C2—C3—C4—C5	−0.15 (16)	C5—C6—C7—O3	2.13 (14)
C2—C3—C4—C9	179.20 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.87 (2)	1.87 (2)	2.6457 (12)	147 (2)
O1—H1···O2ii	0.87 (2)	2.32 (1)	3.0067 (11)	134 (9)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.87 (2)	1.87 (2)	2.6457 (12)	147 (2)
O1—H1⋯O2i	0.87 (2)	2.32 (1)	3.0067 (11)	134 (9)

Symmetry code: (i) .