Isopropyl 3,4-dihy-droxy-benzoate.

In the crystal structure of the title compound, C(10)H(12)O(4), O-H⋯O hydrogen bonds incorporating R(2) (2)(10) and R(2) (2)(14) motifs link mol-ecules into chains along [1[Formula: see text]0]. An intra-molecular O-H⋯O hydrogen bond is also observed.

Related literature

The title compound is a derivative of protocatechuic acid (3,4-dihy­droxy­benzoic acid). For the properties of esters of protocatechuic acid, see: Shizuka et al. (2004 ▶); Yun-Choi et al. (1996 ▶); Robert et al. (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H12O4

M = 196.20

Triclinic,

a = 5.8485 (12) Å

b = 9.1844 (17) Å

c = 9.9834 (19) Å

α = 72.629 (3)°

β = 80.547 (3)°

γ = 78.980 (3)°

V = 499.06 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.37 × 0.25 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

2520 measured reflections

1745 independent reflections

1289 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.133

S = 1.04

1745 reflections

131 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.23 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811044965/lh5339sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044965/lh5339Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811044965/lh5339Isup3.cml

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

C10H12O4	Z = 2
Mr = 196.20	F(000) = 208
Triclinic, P1	Dx = 1.306 Mg m−3
Hall symbol: -P 1	Melting point: 407(1) K
a = 5.8485 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1844 (17) Å	Cell parameters from 666 reflections
c = 9.9834 (19) Å	θ = 2.4–24.2°
α = 72.629 (3)°	µ = 0.10 mm−1
β = 80.547 (3)°	T = 296 K
γ = 78.980 (3)°	Needle, colorless
V = 499.06 (17) Å3	0.37 × 0.25 × 0.15 mm

Bruker APEXII CCD diffractometer	1289 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.012
graphite	θmax = 25.1°, θmin = 2.2°
φ and ω scans	h = −6→6
2520 measured reflections	k = −10→10
1745 independent reflections	l = −9→11

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0685P)2 + 0.037P] where P = (Fo2 + 2Fc2)/3
1745 reflections	(Δ/σ)max < 0.001
131 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.23 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	0.2571 (2)	0.15042 (14)	0.29888 (13)	0.0554 (4)
O2	−0.0069 (2)	0.13603 (15)	0.16625 (15)	0.0666 (5)
O3	0.7691 (2)	−0.42927 (15)	0.09653 (16)	0.0672 (5)
H3	0.7088	−0.4623	0.0452	0.101*
O4	0.3545 (3)	−0.32701 (15)	−0.01531 (15)	0.0667 (5)
H4	0.2461	−0.2741	−0.0586	0.100*
C1	−0.0633 (5)	0.2409 (3)	0.4524 (3)	0.0925 (9)
H1A	−0.1650	0.1839	0.4288	0.139*
H1B	−0.1541	0.3308	0.4754	0.139*
H1C	0.0143	0.1771	0.5321	0.139*
C2	0.2856 (5)	0.3780 (3)	0.3562 (3)	0.0811 (7)
H2A	0.3599	0.3182	0.4385	0.122*
H2B	0.2030	0.4736	0.3715	0.122*
H2C	0.4024	0.3988	0.2762	0.122*
C3	0.1158 (4)	0.2893 (2)	0.3288 (2)	0.0605 (6)
H3A	0.0369	0.3511	0.2462	0.073*
C4	0.1778 (3)	0.0861 (2)	0.21617 (18)	0.0471 (5)
C5	0.3358 (3)	−0.05140 (19)	0.19011 (18)	0.0436 (4)
C6	0.2685 (3)	−0.12546 (19)	0.10392 (18)	0.0463 (5)
H6	0.1255	−0.0895	0.0673	0.056*
C7	0.4099 (3)	−0.25143 (19)	0.07177 (18)	0.0469 (5)
C8	0.6225 (3)	−0.3068 (2)	0.12786 (19)	0.0485 (5)
C9	0.6887 (3)	−0.2345 (2)	0.2151 (2)	0.0553 (5)
H9	0.8301	−0.2720	0.2534	0.066*
C10	0.5479 (3)	−0.1072 (2)	0.2463 (2)	0.0521 (5)
H10	0.5949	−0.0590	0.3047	0.063*

	U11	U22	U33	U12	U13	U23
O1	0.0583 (9)	0.0500 (8)	0.0628 (8)	0.0063 (6)	−0.0190 (7)	−0.0256 (6)
O2	0.0620 (9)	0.0635 (9)	0.0807 (10)	0.0197 (7)	−0.0336 (8)	−0.0342 (8)
O3	0.0612 (9)	0.0555 (8)	0.0889 (11)	0.0185 (7)	−0.0253 (8)	−0.0338 (7)
O4	0.0740 (11)	0.0547 (8)	0.0803 (10)	0.0211 (7)	−0.0381 (8)	−0.0354 (8)
C1	0.0704 (16)	0.107 (2)	0.116 (2)	−0.0091 (14)	0.0063 (15)	−0.0656 (18)
C2	0.0992 (19)	0.0651 (14)	0.0901 (17)	−0.0163 (13)	−0.0072 (14)	−0.0374 (13)
C3	0.0705 (14)	0.0491 (11)	0.0651 (13)	0.0111 (10)	−0.0207 (11)	−0.0265 (10)
C4	0.0507 (11)	0.0447 (10)	0.0442 (10)	−0.0008 (8)	−0.0102 (8)	−0.0110 (8)
C5	0.0439 (10)	0.0397 (9)	0.0434 (10)	−0.0011 (8)	−0.0072 (8)	−0.0077 (8)
C6	0.0433 (10)	0.0438 (10)	0.0492 (10)	0.0045 (8)	−0.0136 (8)	−0.0115 (8)
C7	0.0518 (11)	0.0398 (10)	0.0491 (10)	0.0002 (8)	−0.0119 (8)	−0.0133 (8)
C8	0.0461 (11)	0.0407 (10)	0.0540 (11)	0.0027 (8)	−0.0091 (8)	−0.0101 (8)
C9	0.0452 (11)	0.0516 (11)	0.0684 (13)	0.0057 (9)	−0.0203 (9)	−0.0166 (9)
C10	0.0521 (11)	0.0488 (11)	0.0580 (11)	−0.0020 (9)	−0.0159 (9)	−0.0172 (9)

O1—C4	1.330 (2)	C2—H2B	0.9600
O1—C3	1.464 (2)	C2—H2C	0.9600
O2—C4	1.215 (2)	C3—H3A	0.9800
O3—C8	1.361 (2)	C4—C5	1.479 (2)
O3—H3	0.8200	C5—C6	1.386 (2)
O4—C7	1.372 (2)	C5—C10	1.389 (3)
O4—H4	0.8200	C6—C7	1.377 (2)
C1—C3	1.497 (3)	C6—H6	0.9300
C1—H1A	0.9600	C7—C8	1.391 (3)
C1—H1B	0.9600	C8—C9	1.380 (3)
C1—H1C	0.9600	C9—C10	1.381 (3)
C2—C3	1.502 (3)	C9—H9	0.9300
C2—H2A	0.9600	C10—H10	0.9300
C4—O1—C3	118.03 (14)	O2—C4—O1	123.08 (16)
C8—O3—H3	109.5	O2—C4—C5	123.18 (17)
C7—O4—H4	109.5	O1—C4—C5	113.73 (15)
C3—C1—H1A	109.5	C6—C5—C10	119.21 (16)
C3—C1—H1B	109.5	C6—C5—C4	117.83 (16)
H1A—C1—H1B	109.5	C10—C5—C4	122.95 (17)
C3—C1—H1C	109.5	C7—C6—C5	121.01 (16)
H1A—C1—H1C	109.5	C7—C6—H6	119.5
H1B—C1—H1C	109.5	C5—C6—H6	119.5
C3—C2—H2A	109.5	O4—C7—C6	123.48 (16)
C3—C2—H2B	109.5	O4—C7—C8	116.86 (15)
H2A—C2—H2B	109.5	C6—C7—C8	119.66 (16)
C3—C2—H2C	109.5	O3—C8—C9	119.09 (16)
H2A—C2—H2C	109.5	O3—C8—C7	121.41 (16)
H2B—C2—H2C	109.5	C9—C8—C7	119.49 (16)
O1—C3—C1	108.46 (17)	C8—C9—C10	120.90 (17)
O1—C3—C2	105.88 (17)	C8—C9—H9	119.6
C1—C3—C2	113.43 (18)	C10—C9—H9	119.6
O1—C3—H3A	109.7	C9—C10—C5	119.73 (18)
C1—C3—H3A	109.7	C9—C10—H10	120.1
C2—C3—H3A	109.7	C5—C10—H10	120.1
C4—O1—C3—C1	85.7 (2)	C5—C6—C7—C8	0.8 (3)
C4—O1—C3—C2	−152.21 (17)	O4—C7—C8—O3	0.6 (3)
C3—O1—C4—O2	−0.9 (3)	C6—C7—C8—O3	−178.80 (16)
C3—O1—C4—C5	178.76 (15)	O4—C7—C8—C9	179.39 (17)
O2—C4—C5—C6	0.3 (3)	C6—C7—C8—C9	0.0 (3)
O1—C4—C5—C6	−179.44 (15)	O3—C8—C9—C10	178.19 (17)
O2—C4—C5—C10	179.34 (18)	C7—C8—C9—C10	−0.6 (3)
O1—C4—C5—C10	−0.4 (3)	C8—C9—C10—C5	0.5 (3)
C10—C5—C6—C7	−1.0 (3)	C6—C5—C10—C9	0.3 (3)
C4—C5—C6—C7	178.12 (15)	C4—C5—C10—C9	−178.72 (17)
C5—C6—C7—O4	−178.53 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4i	0.82	2.15	2.844 (2)	142.
O3—H3···O4	0.82	2.28	2.720 (2)	115.
O4—H4···O2ii	0.82	1.93	2.747 (2)	175.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4i	0.82	2.15	2.844 (2)	142
O3—H3⋯O4	0.82	2.28	2.720 (2)	115
O4—H4⋯O2ii	0.82	1.93	2.747 (2)	175

Symmetry codes: (i) ; (ii) .