3,4,5-Trimeth-oxy-phenol.

The asymmetric unit of the title compound, C(9)H(12)O(4), consists of two crystallographically independent mol-ecules with similar conformations: essentially planar [r.m.s deviations for C(6)O(4) = 0.0057 and 0.0137 Å] except for the central meth-oxy-methyl group [C-C-O-C torsion angles = 83.3 (2) and 83.9 (2)°]. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules, generating supra-molecular chains along the b axis.The three-dimensional crystal structure is stabilized by C-H⋯O and C-H⋯π inter-actions.

Related literature

For background information on the energetics and anti-oxidant potential of phenolic compounds, see: Matos et al. (2008 ▶); Gong et al. (2009 ▶).

Experimental

Crystal data

C9H12O4

M = 184.19

Monoclinic,

a = 15.355 (3) Å

b = 11.139 (2) Å

c = 11.546 (2) Å

β = 111.38 (3)°

V = 1839.0 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.981, T max = 0.990

16747 measured reflections

3257 independent reflections

2957 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.123

S = 1.05

3257 reflections

243 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812042997/tk5160sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042997/tk5160Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042997/tk5160Isup3.cml

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

C9H12O4	F(000) = 784
Mr = 184.19	Dx = 1.331 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5944 reflections
a = 15.355 (3) Å	θ = 3.3–25.4°
b = 11.139 (2) Å	µ = 0.11 mm−1
c = 11.546 (2) Å	T = 296 K
β = 111.38 (3)°	Block, colourless
V = 1839.0 (6) Å3	0.20 × 0.15 × 0.10 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	3257 independent reflections
Radiation source: fine-focus sealed tube	2957 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 25.1°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→17
Tmin = 0.981, Tmax = 0.990	k = −13→13
16747 measured reflections	l = −11→13

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0545P)2 + 0.3972P] where P = (Fo2 + 2Fc2)/3
3257 reflections	(Δ/σ)max < 0.001
243 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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. 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 > 2sigma(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	0.33376 (8)	0.41617 (11)	0.19861 (12)	0.0525 (3)
H1	0.3521	0.3629	0.1642	0.079*
O4	0.64034 (9)	0.58079 (12)	0.27042 (13)	0.0602 (4)
O3	0.61501 (8)	0.74092 (10)	0.42789 (11)	0.0509 (3)
C2	0.39182 (12)	0.57694 (14)	0.33613 (15)	0.0445 (4)
H2	0.3366	0.5772	0.3520	0.053*
C3	0.46239 (12)	0.65836 (14)	0.39471 (15)	0.0443 (4)
C5	0.54480 (11)	0.65824 (14)	0.37034 (15)	0.0443 (4)
C7	0.55643 (11)	0.57554 (15)	0.28722 (15)	0.0447 (4)
O2	0.45748 (9)	0.74281 (11)	0.47812 (13)	0.0579 (4)
C9	0.48632 (11)	0.49346 (15)	0.22769 (15)	0.0452 (4)
H9	0.4938	0.4384	0.1715	0.054*
C1	0.40488 (11)	0.49505 (14)	0.25354 (15)	0.0426 (4)
C8	0.64850 (16)	0.5093 (2)	0.1731 (2)	0.0805 (7)
H8A	0.6423	0.4261	0.1903	0.121*
H8B	0.7085	0.5225	0.1673	0.121*
H8C	0.6002	0.5309	0.0958	0.121*
C6	0.67555 (14)	0.7061 (2)	0.55005 (19)	0.0676 (6)
H6A	0.6420	0.7098	0.6057	0.101*
H6B	0.7281	0.7596	0.5786	0.101*
H6C	0.6972	0.6256	0.5478	0.101*
C4	0.38077 (15)	0.73582 (19)	0.5198 (2)	0.0644 (5)
H4A	0.3235	0.7519	0.4514	0.097*
H4B	0.3890	0.7940	0.5843	0.097*
H4C	0.3782	0.6568	0.5517	0.097*
O7	0.11271 (9)	0.75191 (10)	0.18255 (12)	0.0519 (3)
O5	−0.16694 (8)	1.08198 (11)	0.13218 (12)	0.0557 (3)
H5	−0.1501	1.1323	0.1878	0.084*
O6	0.13740 (8)	0.91453 (12)	0.36143 (12)	0.0587 (4)
C16	−0.03779 (12)	0.83857 (15)	0.06267 (15)	0.0462 (4)
C12	0.05455 (11)	0.92090 (15)	0.26236 (15)	0.0440 (4)
C18	−0.10754 (12)	0.92213 (15)	0.05119 (16)	0.0479 (4)
H18	−0.1617	0.9235	−0.0197	0.058*
C14	0.04348 (11)	0.83728 (14)	0.16863 (15)	0.0439 (4)
C11	−0.01507 (11)	1.00391 (15)	0.25244 (15)	0.0456 (4)
H11	−0.0079	1.0590	0.3158	0.055*
O8	−0.04248 (9)	0.75347 (11)	−0.02475 (12)	0.0606 (4)
C10	−0.09552 (11)	1.00336 (15)	0.14650 (16)	0.0450 (4)
C17	−0.11899 (15)	0.75973 (19)	−0.14040 (19)	0.0659 (6)
H17A	−0.1765	0.7496	−0.1266	0.099*
H17B	−0.1131	0.6974	−0.1945	0.099*
H17C	−0.1190	0.8365	−0.1782	0.099*
C15	0.17645 (16)	0.7822 (2)	0.1232 (2)	0.0735 (6)
H15A	0.1450	0.7779	0.0346	0.110*
H15B	0.2279	0.7268	0.1487	0.110*
H15C	0.1994	0.8622	0.1463	0.110*
C13	0.14821 (16)	0.9927 (2)	0.46273 (19)	0.0749 (6)
H13A	0.1435	1.0744	0.4348	0.112*
H13B	0.2084	0.9798	0.5267	0.112*
H13C	0.1001	0.9766	0.4953	0.112*

	U11	U22	U33	U12	U13	U23
O1	0.0433 (6)	0.0543 (8)	0.0560 (7)	−0.0037 (5)	0.0135 (6)	−0.0136 (6)
O4	0.0501 (7)	0.0696 (9)	0.0688 (9)	−0.0055 (6)	0.0311 (7)	−0.0059 (7)
O3	0.0527 (7)	0.0453 (7)	0.0509 (7)	−0.0101 (5)	0.0143 (6)	0.0044 (5)
C2	0.0429 (9)	0.0426 (9)	0.0496 (10)	0.0027 (7)	0.0186 (8)	0.0017 (7)
C3	0.0492 (9)	0.0375 (9)	0.0460 (9)	0.0017 (7)	0.0172 (7)	0.0010 (7)
C5	0.0463 (9)	0.0387 (9)	0.0454 (9)	−0.0035 (7)	0.0139 (7)	0.0049 (7)
C7	0.0438 (9)	0.0461 (10)	0.0458 (9)	0.0033 (7)	0.0182 (7)	0.0074 (7)
O2	0.0614 (8)	0.0503 (7)	0.0698 (9)	−0.0090 (6)	0.0330 (7)	−0.0185 (6)
C9	0.0490 (9)	0.0439 (9)	0.0427 (9)	0.0047 (8)	0.0167 (7)	−0.0002 (7)
C1	0.0406 (8)	0.0418 (9)	0.0408 (8)	0.0029 (7)	0.0092 (7)	0.0035 (7)
C8	0.0706 (14)	0.0924 (17)	0.0975 (17)	−0.0050 (12)	0.0533 (13)	−0.0198 (14)
C6	0.0596 (12)	0.0693 (13)	0.0594 (12)	−0.0081 (10)	0.0047 (10)	0.0066 (10)
C4	0.0720 (13)	0.0632 (12)	0.0698 (13)	−0.0076 (10)	0.0399 (11)	−0.0177 (10)
O7	0.0555 (7)	0.0461 (7)	0.0579 (8)	0.0084 (5)	0.0253 (6)	0.0097 (5)
O5	0.0506 (7)	0.0549 (8)	0.0590 (8)	0.0072 (6)	0.0167 (6)	−0.0080 (6)
O6	0.0483 (7)	0.0689 (9)	0.0505 (7)	0.0006 (6)	0.0079 (6)	−0.0046 (6)
C16	0.0547 (10)	0.0395 (9)	0.0449 (9)	−0.0035 (8)	0.0188 (8)	−0.0016 (7)
C12	0.0416 (9)	0.0468 (10)	0.0434 (9)	−0.0064 (7)	0.0151 (7)	0.0038 (7)
C18	0.0481 (9)	0.0477 (10)	0.0437 (9)	−0.0014 (8)	0.0117 (8)	−0.0004 (7)
C14	0.0459 (9)	0.0402 (9)	0.0478 (9)	0.0005 (7)	0.0197 (8)	0.0048 (7)
C11	0.0493 (10)	0.0442 (9)	0.0448 (9)	−0.0058 (8)	0.0189 (8)	−0.0047 (7)
O8	0.0676 (8)	0.0514 (8)	0.0547 (8)	0.0062 (6)	0.0126 (6)	−0.0130 (6)
C10	0.0444 (9)	0.0419 (9)	0.0516 (10)	−0.0010 (7)	0.0210 (8)	0.0019 (7)
C17	0.0733 (13)	0.0658 (13)	0.0511 (11)	0.0015 (10)	0.0139 (10)	−0.0141 (9)
C15	0.0728 (14)	0.0749 (14)	0.0894 (16)	0.0121 (11)	0.0492 (13)	0.0126 (12)
C13	0.0688 (13)	0.0847 (16)	0.0551 (12)	−0.0053 (12)	0.0034 (10)	−0.0148 (11)

O1—C1	1.364 (2)	O7—C14	1.391 (2)
O1—H1	0.8200	O7—C15	1.425 (2)
O4—C7	1.372 (2)	O5—C10	1.366 (2)
O4—C8	1.420 (2)	O5—H5	0.8200
O3—C5	1.389 (2)	O6—C12	1.368 (2)
O3—C6	1.431 (2)	O6—C13	1.418 (2)
C2—C3	1.386 (2)	C16—O8	1.367 (2)
C2—C1	1.386 (2)	C16—C18	1.388 (2)
C2—H2	0.9300	C16—C14	1.393 (2)
C3—O2	1.368 (2)	C12—C11	1.386 (2)
C3—C5	1.393 (2)	C12—C14	1.391 (2)
C5—C7	1.388 (2)	C18—C10	1.384 (2)
C7—C9	1.389 (2)	C18—H18	0.9300
O2—C4	1.428 (2)	C11—C10	1.386 (2)
C9—C1	1.388 (2)	C11—H11	0.9300
C9—H9	0.9300	O8—C17	1.423 (2)
C8—H8A	0.9600	C17—H17A	0.9600
C8—H8B	0.9600	C17—H17B	0.9600
C8—H8C	0.9600	C17—H17C	0.9600
C6—H6A	0.9600	C15—H15A	0.9600
C6—H6B	0.9600	C15—H15B	0.9600
C6—H6C	0.9600	C15—H15C	0.9600
C4—H4A	0.9600	C13—H13A	0.9600
C4—H4B	0.9600	C13—H13B	0.9600
C4—H4C	0.9600	C13—H13C	0.9600
C1—O1—H1	109.5	C14—O7—C15	114.37 (14)
C7—O4—C8	116.51 (15)	C10—O5—H5	109.5
C5—O3—C6	113.81 (13)	C12—O6—C13	116.83 (15)
C3—C2—C1	118.89 (16)	O8—C16—C18	124.27 (16)
C3—C2—H2	120.6	O8—C16—C14	115.49 (15)
C1—C2—H2	120.6	C18—C16—C14	120.24 (15)
O2—C3—C2	124.04 (15)	O6—C12—C11	123.91 (15)
O2—C3—C5	115.48 (15)	O6—C12—C14	115.38 (15)
C2—C3—C5	120.48 (15)	C11—C12—C14	120.71 (15)
C7—C5—O3	119.84 (15)	C10—C18—C16	119.19 (16)
C7—C5—C3	119.71 (15)	C10—C18—H18	120.4
O3—C5—C3	120.44 (15)	C16—C18—H18	120.4
O4—C7—C5	115.70 (15)	C12—C14—O7	119.76 (15)
O4—C7—C9	123.82 (15)	C12—C14—C16	119.52 (15)
C5—C7—C9	120.48 (15)	O7—C14—C16	120.71 (15)
C3—O2—C4	117.63 (14)	C10—C11—C12	118.84 (15)
C1—C9—C7	118.82 (15)	C10—C11—H11	120.6
C1—C9—H9	120.6	C12—C11—H11	120.6
C7—C9—H9	120.6	C16—O8—C17	117.52 (14)
O1—C1—C2	116.85 (15)	O5—C10—C18	117.03 (15)
O1—C1—C9	121.55 (15)	O5—C10—C11	121.48 (15)
C2—C1—C9	121.61 (15)	C18—C10—C11	121.49 (16)
O4—C8—H8A	109.5	O8—C17—H17A	109.5
O4—C8—H8B	109.5	O8—C17—H17B	109.5
H8A—C8—H8B	109.5	H17A—C17—H17B	109.5
O4—C8—H8C	109.5	O8—C17—H17C	109.5
H8A—C8—H8C	109.5	H17A—C17—H17C	109.5
H8B—C8—H8C	109.5	H17B—C17—H17C	109.5
O3—C6—H6A	109.5	O7—C15—H15A	109.5
O3—C6—H6B	109.5	O7—C15—H15B	109.5
H6A—C6—H6B	109.5	H15A—C15—H15B	109.5
O3—C6—H6C	109.5	O7—C15—H15C	109.5
H6A—C6—H6C	109.5	H15A—C15—H15C	109.5
H6B—C6—H6C	109.5	H15B—C15—H15C	109.5
O2—C4—H4A	109.5	O6—C13—H13A	109.5
O2—C4—H4B	109.5	O6—C13—H13B	109.5
H4A—C4—H4B	109.5	H13A—C13—H13B	109.5
O2—C4—H4C	109.5	O6—C13—H13C	109.5
H4A—C4—H4C	109.5	H13A—C13—H13C	109.5
H4B—C4—H4C	109.5	H13B—C13—H13C	109.5
C1—C2—C3—O2	−179.75 (15)	C13—O6—C12—C11	4.7 (2)
C1—C2—C3—C5	0.4 (2)	C13—O6—C12—C14	−175.54 (17)
C6—O3—C5—C7	−97.21 (19)	O8—C16—C18—C10	179.30 (16)
C6—O3—C5—C3	83.3 (2)	C14—C16—C18—C10	−0.4 (3)
O2—C3—C5—C7	179.80 (15)	O6—C12—C14—O7	2.6 (2)
C2—C3—C5—C7	−0.3 (2)	C11—C12—C14—O7	−177.60 (14)
O2—C3—C5—O3	−0.7 (2)	O6—C12—C14—C16	−178.57 (15)
C2—C3—C5—O3	179.16 (14)	C11—C12—C14—C16	1.2 (2)
C8—O4—C7—C5	−171.18 (17)	C15—O7—C14—C12	−97.3 (2)
C8—O4—C7—C9	9.5 (3)	C15—O7—C14—C16	83.9 (2)
O3—C5—C7—O4	1.5 (2)	O8—C16—C14—C12	179.76 (15)
C3—C5—C7—O4	−179.02 (15)	C18—C16—C14—C12	−0.5 (2)
O3—C5—C7—C9	−179.10 (14)	O8—C16—C14—O7	−1.5 (2)
C3—C5—C7—C9	0.4 (2)	C18—C16—C14—O7	178.29 (15)
C2—C3—O2—C4	8.9 (2)	O6—C12—C11—C10	178.80 (15)
C5—C3—O2—C4	−171.24 (16)	C14—C12—C11—C10	−0.9 (2)
O4—C7—C9—C1	178.85 (15)	C18—C16—O8—C17	7.3 (3)
C5—C7—C9—C1	−0.5 (2)	C14—C16—O8—C17	−173.01 (16)
C3—C2—C1—O1	179.64 (14)	C16—C18—C10—O5	−178.55 (15)
C3—C2—C1—C9	−0.5 (2)	C16—C18—C10—C11	0.7 (3)
C7—C9—C1—O1	−179.58 (14)	C12—C11—C10—O5	179.19 (15)
C7—C9—C1—C2	0.6 (2)	C12—C11—C10—C18	0.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O7i	0.82	1.93	2.7484 (18)	179
O1—H1···O3ii	0.82	1.90	2.7204 (17)	175
C6—H6A···O1iii	0.96	2.57	3.256 (3)	129
C15—H15A···O5iv	0.96	2.59	3.270 (3)	128
C4—H4B···Cg1v	0.96	2.86	3.777 (2)	160
C17—H17B···Cg2vi	0.96	2.85	3.736 (2)	154
C13—H13B···O1vii	0.96	2.49	3.303 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C3,C5,C7,C9 and C10–C12,C14,C16,C18 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O7i	0.82	1.93	2.7484 (18)	179
O1—H1⋯O3ii	0.82	1.90	2.7204 (17)	175
C6—H6A⋯O1iii	0.96	2.57	3.256 (3)	129
C15—H15A⋯O5iv	0.96	2.59	3.270 (3)	128
C4—H4B⋯Cg1v	0.96	2.86	3.777 (2)	160
C17—H17B⋯Cg2vi	0.96	2.85	3.736 (2)	154
C13—H13B⋯O1vii	0.96	2.49	3.303 (3)	142

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .