Isopropyl 3,4,5-trihy-droxy-benzoate.

In the title compound, C(10)H(12)O(5), the dihedral angle between the benzene ring is almost coplanar with the attached C(O)-O-C group [dihedral angle = 0.32 (15)°]. In the crystal, two intermolecular O-H⋯O hydrogen bonds make R(4) (4)(26) ring mofits.

Related literature

For the properties of isopropyl gallate, see: Calheiros et al. (2008 ▶); Morais et al. (2010 ▶). For the synthesis method, see: Christiansen (1926 ▶); Li et al. (2001 ▶). For the hydrogen-bonding pattern, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H12O5

M = 212.20

Monoclinic,

a = 19.148 (6) Å

b = 4.7030 (15) Å

c = 11.571 (4) Å

β = 90.159 (5)°

V = 1042.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.31 × 0.29 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.967, T max = 0.977

5181 measured reflections

2055 independent reflections

1589 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.132

S = 1.05

2055 reflections

141 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812004278/mw2052sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004278/mw2052Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004278/mw2052Isup3.cml

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

C10H12O5	F(000) = 448
Mr = 212.20	Dx = 1.353 Mg m−3
Monoclinic, P21/c	Melting point: 396(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 19.148 (6) Å	Cell parameters from 1697 reflections
b = 4.7030 (15) Å	θ = 3.5–25.7°
c = 11.571 (4) Å	µ = 0.11 mm−1
β = 90.159 (5)°	T = 296 K
V = 1042.0 (6) Å3	Block, colourless
Z = 4	0.31 × 0.29 × 0.21 mm

Bruker APEXII CCD diffractometer	2055 independent reflections
Radiation source: fine-focus sealed tube	1589 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 26.1°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→23
Tmin = 0.967, Tmax = 0.977	k = −5→5
5181 measured reflections	l = −14→12

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0778P)2 + 0.0222P] where P = (Fo2 + 2Fc2)/3
2055 reflections	(Δ/σ)max < 0.001
141 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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.

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 > σ(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	0.46197 (5)	−0.0043 (2)	0.24204 (10)	0.0447 (3)
H1	0.4823	−0.1535	0.2275	0.067*
O2	0.45282 (6)	−0.3102 (3)	0.04068 (10)	0.0478 (3)
H2	0.4449	−0.3814	−0.0227	0.072*
O3	0.34242 (6)	−0.2621 (3)	−0.09898 (9)	0.0485 (4)
H3	0.3094	−0.2187	−0.1407	0.073*
O4	0.23999 (6)	0.5891 (3)	0.25056 (9)	0.0462 (4)
O5	0.18797 (6)	0.4562 (3)	0.08655 (10)	0.0476 (4)
C1	0.35320 (8)	0.2096 (3)	0.20035 (12)	0.0349 (4)
H1A	0.3564	0.3109	0.2692	0.042*
C2	0.40505 (7)	0.0233 (3)	0.17032 (13)	0.0337 (4)
C3	0.40050 (7)	−0.1299 (3)	0.06846 (12)	0.0341 (4)
C4	0.34216 (8)	−0.0952 (3)	−0.00283 (12)	0.0339 (4)
C5	0.29047 (8)	0.0934 (3)	0.02583 (12)	0.0354 (4)
H5	0.2522	0.1181	−0.0227	0.042*
C6	0.29573 (7)	0.2479 (3)	0.12825 (12)	0.0329 (4)
C7	0.24087 (8)	0.4472 (3)	0.16310 (13)	0.0356 (4)
C8	0.13112 (9)	0.6509 (4)	0.10811 (16)	0.0549 (5)
H8	0.1488	0.8212	0.1473	0.066*
C9	0.10338 (12)	0.7293 (5)	−0.0096 (2)	0.0821 (8)
H9A	0.1394	0.8223	−0.0530	0.123*
H9B	0.0643	0.8552	−0.0012	0.123*
H9C	0.0888	0.5603	−0.0495	0.123*
C10	0.07847 (11)	0.5047 (6)	0.1831 (2)	0.0847 (8)
H10A	0.0618	0.3367	0.1448	0.127*
H10B	0.0400	0.6308	0.1974	0.127*
H10C	0.0999	0.4529	0.2552	0.127*

	U11	U22	U33	U12	U13	U23
O1	0.0373 (6)	0.0438 (7)	0.0530 (7)	0.0058 (5)	−0.0220 (5)	−0.0060 (5)
O2	0.0415 (7)	0.0523 (8)	0.0495 (7)	0.0136 (6)	−0.0065 (5)	−0.0082 (6)
O3	0.0558 (7)	0.0553 (8)	0.0344 (6)	0.0150 (6)	−0.0117 (5)	−0.0108 (5)
O4	0.0429 (7)	0.0565 (8)	0.0391 (7)	0.0089 (5)	−0.0089 (5)	−0.0104 (5)
O5	0.0350 (6)	0.0611 (8)	0.0467 (7)	0.0134 (5)	−0.0145 (5)	−0.0123 (5)
C1	0.0370 (8)	0.0361 (9)	0.0315 (8)	−0.0020 (7)	−0.0077 (6)	−0.0006 (6)
C2	0.0293 (7)	0.0349 (9)	0.0369 (8)	−0.0032 (6)	−0.0097 (6)	0.0038 (6)
C3	0.0322 (8)	0.0332 (8)	0.0370 (8)	0.0027 (6)	−0.0023 (6)	0.0043 (6)
C4	0.0367 (8)	0.0376 (9)	0.0274 (7)	0.0000 (6)	−0.0028 (6)	0.0007 (6)
C5	0.0333 (8)	0.0428 (9)	0.0300 (8)	0.0003 (6)	−0.0087 (6)	0.0030 (6)
C6	0.0308 (7)	0.0370 (9)	0.0310 (8)	−0.0003 (6)	−0.0044 (6)	0.0033 (6)
C7	0.0331 (8)	0.0429 (9)	0.0308 (8)	−0.0013 (7)	−0.0069 (6)	0.0018 (7)
C8	0.0375 (9)	0.0619 (13)	0.0653 (12)	0.0159 (9)	−0.0152 (8)	−0.0146 (10)
C9	0.0632 (13)	0.0969 (19)	0.0860 (16)	0.0249 (13)	−0.0316 (11)	0.0047 (13)
C10	0.0523 (13)	0.120 (2)	0.0817 (16)	0.0100 (13)	0.0083 (11)	−0.0198 (14)

O1—C2	1.3741 (16)	C4—C5	1.371 (2)
O1—H1	0.8200	C5—C6	1.394 (2)
O2—C3	1.3519 (18)	C5—H5	0.9300
O2—H2	0.8200	C6—C7	1.465 (2)
O3—C4	1.3616 (19)	C8—C10	1.499 (3)
O3—H3	0.8200	C8—C9	1.506 (3)
O4—C7	1.2122 (19)	C8—H8	0.9800
O5—C7	1.3443 (17)	C9—H9A	0.9600
O5—C8	1.445 (2)	C9—H9B	0.9600
C1—C2	1.370 (2)	C9—H9C	0.9600
C1—C6	1.3909 (19)	C10—H10A	0.9600
C1—H1A	0.9300	C10—H10B	0.9600
C2—C3	1.384 (2)	C10—H10C	0.9600
C3—C4	1.397 (2)
C2—O1—H1	109.5	O4—C7—O5	121.38 (14)
C3—O2—H2	109.5	O4—C7—C6	126.39 (13)
C4—O3—H3	109.5	O5—C7—C6	112.22 (13)
C7—O5—C8	118.22 (13)	O5—C8—C10	108.52 (18)
C2—C1—C6	120.23 (14)	O5—C8—C9	105.25 (16)
C2—C1—H1A	119.9	C10—C8—C9	113.57 (18)
C6—C1—H1A	119.9	O5—C8—H8	109.8
C1—C2—O1	118.78 (13)	C10—C8—H8	109.8
C1—C2—C3	120.34 (13)	C9—C8—H8	109.8
O1—C2—C3	120.86 (14)	C8—C9—H9A	109.5
O2—C3—C2	118.96 (12)	C8—C9—H9B	109.5
O2—C3—C4	121.67 (13)	H9A—C9—H9B	109.5
C2—C3—C4	119.37 (14)	C8—C9—H9C	109.5
O3—C4—C5	125.10 (13)	H9A—C9—H9C	109.5
O3—C4—C3	114.24 (14)	H9B—C9—H9C	109.5
C5—C4—C3	120.66 (13)	C8—C10—H10A	109.5
C4—C5—C6	119.51 (13)	C8—C10—H10B	109.5
C4—C5—H5	120.2	H10A—C10—H10B	109.5
C6—C5—H5	120.2	C8—C10—H10C	109.5
C1—C6—C5	119.86 (14)	H10A—C10—H10C	109.5
C1—C6—C7	118.98 (13)	H10B—C10—H10C	109.5
C5—C6—C7	121.15 (13)
C6—C1—C2—O1	178.39 (14)	C2—C1—C6—C5	0.8 (2)
C6—C1—C2—C3	−0.5 (2)	C2—C1—C6—C7	179.57 (13)
C1—C2—C3—O2	179.39 (13)	C4—C5—C6—C1	0.0 (2)
O1—C2—C3—O2	0.6 (2)	C4—C5—C6—C7	−178.73 (13)
C1—C2—C3—C4	−0.7 (2)	C8—O5—C7—O4	3.0 (2)
O1—C2—C3—C4	−179.53 (13)	C8—O5—C7—C6	−178.08 (14)
O2—C3—C4—O3	1.6 (2)	C1—C6—C7—O4	0.5 (2)
C2—C3—C4—O3	−178.31 (14)	C5—C6—C7—O4	179.19 (16)
O2—C3—C4—C5	−178.57 (14)	C1—C6—C7—O5	−178.35 (13)
C2—C3—C4—C5	1.5 (2)	C5—C6—C7—O5	0.4 (2)
O3—C4—C5—C6	178.66 (14)	C7—O5—C8—C10	−87.29 (19)
C3—C4—C5—C6	−1.2 (2)	C7—O5—C8—C9	150.82 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1i	0.82	2.00	2.772 (2)	158
O3—H3···O4ii	0.82	1.93	2.742 (2)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1i	0.82	2.00	2.772 (2)	158
O3—H3⋯O4ii	0.82	1.93	2.742 (2)	173

Symmetry codes: (i) ; (ii) .