Crystal structure of 3,4-di-meth-oxy-phenol.

The title compound, C8H10O3, has two planar mol-ecules in the asymmetric unit possessing mean deviations from planarity of 0.051 and 0.071 Å. In the crystal, there are two distinct infinite chains, both along [010]. The chains are formed by O-H⋯O inter-actions between the phenol and both the 3-meth-oxy and the 4-meth-oxy groups.

Related literature

For the crystal structure of the related 4-[(2,3-di­methyl­but-3-en-2-yl)­oxy]-3-meth­oxy­phenol, see: Yamamoto et al. (2014 ▸). For the crystal structure of 3,4,5-tri­meth­oxy­phenol, see: Jia et al. (2012 ▸). For background and crystal structures solved during the study, see: McDonald et al. (2015 ▸); Nguyen et al. (2015 ▸).

Experimental

Crystal data

C8H10O3

M = 154.16

Orthorhombic,

a = 8.7477 (4) Å

b = 13.8218 (7) Å

c = 26.6422 (13) Å

V = 3221.3 (3) Å3

Z = 16

Mo Kα radiation

μ = 0.10 mm−1

T = 120 K

0.5 × 0.4 × 0.4 mm

Data collection

Bruker Venture D8 CMOS diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2014 ▸) T min = 0.700, T max = 0.746

29914 measured reflections

3996 independent reflections

3360 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.116

S = 1.04

3996 reflections

205 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2014 ▸); cell refinement: SAINT (Bruker, 2014 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸) and olex2.refine (Bourhis et al., 2015 ▸); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▸); software used to prepare material for publication: OLEX2 and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015022860/ff2145sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015022860/ff2145Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015022860/ff2145Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015022860/ff2145fig1.tif

Mol­ecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are drawn as spheres of arbitrary radius.

Click here for additional data file.

. DOI: 10.1107/S2056989015022860/ff2145fig2.tif

Mol­ecular packing of the title compound with hydrogen bonding shown as dashed lines.

CCDC reference: 1439495

Additional supporting information: crystallographic information; 3D view; checkCIF report

C8H10O3	F(000) = 1312
Mr = 154.16	Dx = 1.271 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9890 reflections
a = 8.7477 (4) Å	θ = 3.0–28.3°
b = 13.8218 (7) Å	µ = 0.10 mm−1
c = 26.6422 (13) Å	T = 120 K
V = 3221.3 (3) Å3	Block, brown
Z = 16	0.5 × 0.4 × 0.4 mm

Bruker Venture D8 CMOS diffractometer	3996 independent reflections
Radiation source: Mo	3360 reflections with I > 2σ(I)
TRIUMPH monochromator	Rint = 0.032
φ and ω scans	θmax = 28.4°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −11→10
Tmin = 0.700, Tmax = 0.746	k = −18→18
29914 measured reflections	l = −35→34

Refinement on F2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0552P)2 + 1.1413P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3996 reflections	Δρmax = 0.25 e Å−3
205 parameters	Δρmin = −0.25 e Å−3

Experimental. Absorption correction: SADABS2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0791 before and 0.0531 after correction. The Ratio of minimum to maximum transmission is 0.9391. The λ/2 correction factor is 0.00150.

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.

	x	y	z	Uiso*/Ueq
O1	0.31642 (12)	0.55792 (6)	0.46341 (4)	0.0364 (2)
H1	0.2656 (18)	0.6010 (10)	0.4472 (6)	0.055*
O2	0.41171 (10)	0.21648 (5)	0.45901 (3)	0.0274 (2)
O3	0.23732 (11)	0.19341 (6)	0.38304 (3)	0.0322 (2)
C1	0.29128 (13)	0.46989 (8)	0.44100 (4)	0.0244 (2)
C2	0.36772 (12)	0.39078 (7)	0.46188 (4)	0.0215 (2)
H2	0.4337	0.3994	0.4899	0.026*
C3	0.34642 (12)	0.29982 (7)	0.44142 (4)	0.0198 (2)
C4	0.25063 (13)	0.28729 (8)	0.39961 (4)	0.0224 (2)
C5	0.17669 (14)	0.36617 (8)	0.37932 (4)	0.0267 (2)
H5	0.1123	0.3579	0.3509	0.032*
C6	0.19567 (14)	0.45826 (8)	0.40017 (5)	0.0280 (3)
H6	0.1433	0.5123	0.3864	0.034*
C7	0.49570 (17)	0.22270 (9)	0.50473 (5)	0.0374 (3)
H7A	0.5365	0.1588	0.5133	0.056*
H7B	0.5803	0.2685	0.5006	0.056*
H7C	0.4280	0.2451	0.5317	0.056*
C8	0.1208 (2)	0.17531 (11)	0.34658 (6)	0.0538 (5)
H8A	0.1214	0.1066	0.3375	0.081*
H8B	0.0209	0.1924	0.3607	0.081*
H8C	0.1402	0.2145	0.3166	0.081*
O4	0.27270 (14)	0.84893 (7)	0.72098 (4)	0.0463 (3)
H4	0.319 (2)	0.8911 (12)	0.7029 (7)	0.069*
O5	0.06921 (10)	0.52789 (6)	0.71498 (3)	0.0313 (2)
O6	0.20065 (12)	0.49211 (7)	0.63132 (3)	0.0370 (2)
C9	0.26184 (15)	0.76288 (9)	0.69618 (5)	0.0313 (3)
C10	0.17021 (14)	0.69220 (9)	0.71881 (5)	0.0288 (3)
H10	0.1198	0.7055	0.7496	0.035*
C11	0.15354 (13)	0.60291 (8)	0.69608 (4)	0.0250 (2)
C12	0.22572 (14)	0.58329 (9)	0.65010 (4)	0.0278 (3)
C13	0.31638 (15)	0.65389 (10)	0.62848 (5)	0.0337 (3)
H13	0.3660	0.6411	0.5975	0.040*
C14	0.33589 (15)	0.74365 (10)	0.65161 (5)	0.0346 (3)
H14	0.3998	0.7912	0.6367	0.042*
C15	0.01260 (18)	0.53863 (10)	0.76497 (5)	0.0403 (3)
H15A	−0.0456	0.4808	0.7744	0.060*
H15B	0.0986	0.5469	0.7881	0.060*
H15C	−0.0540	0.5955	0.7667	0.060*
C16	0.2624 (2)	0.47148 (13)	0.58306 (6)	0.0560 (5)
H16A	0.2374	0.4048	0.5737	0.084*
H16B	0.2187	0.5161	0.5583	0.084*
H16C	0.3737	0.4794	0.5839	0.084*

	U11	U22	U33	U12	U13	U23
O1	0.0473 (6)	0.0169 (4)	0.0450 (5)	0.0030 (4)	−0.0158 (4)	−0.0031 (4)
O2	0.0317 (4)	0.0177 (4)	0.0326 (4)	0.0028 (3)	−0.0104 (3)	0.0003 (3)
O3	0.0436 (5)	0.0208 (4)	0.0322 (4)	−0.0027 (4)	−0.0134 (4)	−0.0036 (3)
C1	0.0267 (5)	0.0170 (5)	0.0295 (6)	−0.0015 (4)	−0.0012 (4)	0.0002 (4)
C2	0.0210 (5)	0.0201 (5)	0.0234 (5)	−0.0016 (4)	−0.0024 (4)	0.0003 (4)
C3	0.0189 (5)	0.0179 (5)	0.0227 (5)	0.0003 (4)	0.0007 (4)	0.0030 (4)
C4	0.0248 (5)	0.0195 (5)	0.0229 (5)	−0.0038 (4)	−0.0008 (4)	0.0002 (4)
C5	0.0282 (6)	0.0260 (5)	0.0260 (5)	−0.0040 (5)	−0.0078 (4)	0.0042 (4)
C6	0.0292 (6)	0.0212 (5)	0.0337 (6)	0.0008 (4)	−0.0067 (5)	0.0070 (4)
C7	0.0450 (7)	0.0256 (6)	0.0416 (7)	0.0050 (5)	−0.0209 (6)	0.0027 (5)
C8	0.0796 (12)	0.0334 (7)	0.0484 (9)	−0.0055 (8)	−0.0363 (8)	−0.0082 (6)
O4	0.0618 (7)	0.0258 (5)	0.0513 (6)	−0.0033 (5)	0.0108 (5)	0.0018 (4)
O5	0.0317 (4)	0.0287 (4)	0.0335 (5)	−0.0021 (3)	0.0081 (4)	0.0079 (3)
O6	0.0491 (6)	0.0340 (5)	0.0279 (4)	−0.0052 (4)	0.0066 (4)	−0.0012 (4)
C9	0.0318 (6)	0.0236 (5)	0.0385 (6)	0.0032 (5)	0.0006 (5)	0.0063 (5)
C10	0.0289 (6)	0.0269 (6)	0.0306 (6)	0.0062 (5)	0.0052 (5)	0.0065 (4)
C11	0.0207 (5)	0.0261 (5)	0.0283 (6)	0.0021 (4)	0.0008 (4)	0.0097 (4)
C12	0.0277 (6)	0.0288 (6)	0.0269 (6)	0.0013 (5)	0.0000 (4)	0.0056 (5)
C13	0.0346 (7)	0.0366 (6)	0.0300 (6)	0.0012 (5)	0.0094 (5)	0.0081 (5)
C14	0.0313 (6)	0.0311 (6)	0.0413 (7)	−0.0012 (5)	0.0077 (5)	0.0124 (5)
C15	0.0448 (8)	0.0339 (6)	0.0421 (7)	0.0050 (6)	0.0214 (6)	0.0106 (6)
C16	0.0853 (13)	0.0480 (9)	0.0348 (7)	−0.0094 (9)	0.0195 (8)	−0.0073 (7)

O1—H1	0.859 (5)	O4—H4	0.860 (5)
O1—C1	1.3731 (13)	O4—C9	1.3638 (16)
O2—C3	1.3684 (12)	O5—C11	1.3686 (14)
O2—C7	1.4251 (14)	O5—C15	1.4285 (15)
O3—C4	1.3754 (13)	O6—C12	1.3735 (15)
O3—C8	1.4302 (16)	O6—C16	1.4236 (17)
C1—C2	1.3971 (15)	C9—C10	1.4002 (17)
C1—C6	1.3816 (16)	C9—C14	1.3786 (18)
C2—H2	0.9500	C10—H10	0.9500
C2—C3	1.3829 (14)	C10—C11	1.3824 (17)
C3—C4	1.4048 (15)	C11—C12	1.4045 (16)
C4—C5	1.3781 (16)	C12—C13	1.3831 (17)
C5—H5	0.9500	C13—H13	0.9500
C5—C6	1.3986 (16)	C13—C14	1.3957 (19)
C6—H6	0.9500	C14—H14	0.9500
C7—H7A	0.9800	C15—H15A	0.9800
C7—H7B	0.9800	C15—H15B	0.9800
C7—H7C	0.9800	C15—H15C	0.9800
C8—H8A	0.9800	C16—H16A	0.9800
C8—H8B	0.9800	C16—H16B	0.9800
C8—H8C	0.9800	C16—H16C	0.9800
C1—O1—H1	108.2 (13)	C9—O4—H4	110.7 (14)
C3—O2—C7	117.19 (9)	C11—O5—C15	116.82 (10)
C4—O3—C8	116.31 (10)	C12—O6—C16	116.88 (11)
O1—C1—C2	116.34 (10)	O4—C9—C10	116.09 (11)
O1—C1—C6	122.85 (10)	O4—C9—C14	123.55 (12)
C6—C1—C2	120.81 (10)	C14—C9—C10	120.35 (12)
C1—C2—H2	120.3	C9—C10—H10	120.2
C3—C2—C1	119.35 (10)	C11—C10—C9	119.65 (11)
C3—C2—H2	120.3	C11—C10—H10	120.2
O2—C3—C2	125.04 (9)	O5—C11—C10	124.89 (11)
O2—C3—C4	114.63 (9)	O5—C11—C12	114.65 (10)
C2—C3—C4	120.33 (9)	C10—C11—C12	120.47 (11)
O3—C4—C3	114.92 (9)	O6—C12—C11	115.02 (10)
O3—C4—C5	125.51 (10)	O6—C12—C13	125.96 (11)
C5—C4—C3	119.56 (10)	C13—C12—C11	119.00 (11)
C4—C5—H5	119.7	C12—C13—H13	119.6
C4—C5—C6	120.57 (10)	C12—C13—C14	120.89 (12)
C6—C5—H5	119.7	C14—C13—H13	119.6
C1—C6—C5	119.37 (10)	C9—C14—C13	119.62 (11)
C1—C6—H6	120.3	C9—C14—H14	120.2
C5—C6—H6	120.3	C13—C14—H14	120.2
O2—C7—H7A	109.5	O5—C15—H15A	109.5
O2—C7—H7B	109.5	O5—C15—H15B	109.5
O2—C7—H7C	109.5	O5—C15—H15C	109.5
H7A—C7—H7B	109.5	H15A—C15—H15B	109.5
H7A—C7—H7C	109.5	H15A—C15—H15C	109.5
H7B—C7—H7C	109.5	H15B—C15—H15C	109.5
O3—C8—H8A	109.5	O6—C16—H16A	109.5
O3—C8—H8B	109.5	O6—C16—H16B	109.5
O3—C8—H8C	109.5	O6—C16—H16C	109.5
H8A—C8—H8B	109.5	H16A—C16—H16B	109.5
H8A—C8—H8C	109.5	H16A—C16—H16C	109.5
H8B—C8—H8C	109.5	H16B—C16—H16C	109.5
O1—C1—C2—C3	179.40 (10)	O4—C9—C10—C11	−179.88 (11)
O1—C1—C6—C5	179.69 (11)	O4—C9—C14—C13	−179.08 (12)
O2—C3—C4—O3	0.15 (14)	O5—C11—C12—O6	−0.06 (15)
O2—C3—C4—C5	178.86 (10)	O5—C11—C12—C13	−178.59 (11)
O3—C4—C5—C6	178.24 (11)	O6—C12—C13—C14	−178.68 (12)
C1—C2—C3—O2	−178.48 (10)	C9—C10—C11—O5	178.92 (11)
C1—C2—C3—C4	0.94 (16)	C9—C10—C11—C12	−1.08 (17)
C2—C1—C6—C5	−0.61 (18)	C10—C9—C14—C13	1.42 (19)
C2—C3—C4—O3	−179.33 (10)	C10—C11—C12—O6	179.94 (11)
C2—C3—C4—C5	−0.62 (16)	C10—C11—C12—C13	1.41 (17)
C3—C4—C5—C6	−0.32 (18)	C11—C12—C13—C14	−0.32 (19)
C4—C5—C6—C1	0.93 (18)	C12—C13—C14—C9	−1.1 (2)
C6—C1—C2—C3	−0.32 (17)	C14—C9—C10—C11	−0.34 (19)
C7—O2—C3—C2	6.52 (16)	C15—O5—C11—C10	−9.16 (17)
C7—O2—C3—C4	−172.93 (11)	C15—O5—C11—C12	170.84 (11)
C8—O3—C4—C3	169.24 (12)	C16—O6—C12—C11	175.56 (13)
C8—O3—C4—C5	−9.38 (18)	C16—O6—C12—C13	−6.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.86 (1)	2.25 (1)	2.9663 (12)	141 (2)
O1—H1···O3i	0.86 (1)	2.13 (1)	2.8834 (13)	145 (2)
O4—H4···O5i	0.86 (1)	2.15 (2)	2.8384 (13)	137 (2)
O4—H4···O6i	0.86 (1)	2.37 (1)	3.1107 (14)	145 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.86 (1)	2.25 (1)	2.9663 (12)	141 (2)
O1—H1⋯O3i	0.86 (1)	2.13 (1)	2.8834 (13)	145 (2)
O4—H4⋯O5i	0.86 (1)	2.15 (2)	2.8384 (13)	137 (2)
O4—H4⋯O6i	0.86 (1)	2.37 (1)	3.1107 (14)	145 (2)

Symmetry code: (i) .