1-(2-Hydr-oxy-3,4-dimethoxy-phen-yl)-2-(4-methoxy-phen-yl)ethanone.

In the title compound, C(17)H(18)O(5), the pyrogallol group is almost coplanar with the mean plane of the attached carbonyl group [dihedral angle of 1.95 (13)°] and makes a dihedral angle of 56.01 (10)° with the other benzene ring. Of the three meth-oxy groups, only one is significantly twisted relative to its attached benzene ring [C-O-C-C torsion angles of 4.0 (5), 3.9 (6) and -106.3 (4)°]. Intra-molecular O-H⋯O and C-H⋯O hydrogen bonds help to establish the conformation, and the packing is consolidated by C-H⋯O inter-actions and π-π stacking interactions [centroid-centroid separation = 3.735 (2) Å].

Related literature

For background on the properties of deoxy­benzoins, see: Kiuchi et al. (1990 ▶); Li et al. (2008 ▶); Niwa et al. (1999 ▶); Papoutsi et al. (2007 ▶); Parmar et al. (1996 ▶); Sanduja et al. (1985 ▶); Xiao et al. (2008 ▶); Xiao, Fang et al. (2007 ▶); Xiao, Shi et al. (2007 ▶).

Experimental

Crystal data

C17H18O5

M = 302.31

Monoclinic,

a = 14.431 (3) Å

b = 14.073 (3) Å

c = 7.4610 (15) Å

β = 92.86 (3)°

V = 1513.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 (2) K

0.30 × 0.30 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.971, T max = 0.971

2893 measured reflections

2667 independent reflections

1543 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.215

S = 1.03

2667 reflections

206 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.35 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536808036258/hb2823sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036258/hb2823Isup2.hkl

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

C17H18O5	F000 = 640
Mr = 302.31	Dx = 1.327 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1217 reflections
a = 14.431 (3) Å	θ = 1.6–24.7º
b = 14.073 (3) Å	µ = 0.10 mm−1
c = 7.4610 (15) Å	T = 293 (2) K
β = 92.86 (3)º	Block, light-yellow
V = 1513.3 (5) Å3	0.30 × 0.30 × 0.30 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	2667 independent reflections
Radiation source: fine-focus sealed tube	1543 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.059
T = 293(2) K	θmax = 25.0º
ω/2θ scans	θmin = 1.4º
Absorption correction: ψ scan(North et al., 1968)	h = −17→17
Tmin = 0.971, Tmax = 0.971	k = −16→0
2893 measured reflections	l = 0→8

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difmap and geom
R[F2 > 2σ(F2)] = 0.071	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.215	w = 1/[σ2(Fo2) + (0.1231P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2667 reflections	Δρmax = 0.28 e Å−3
206 parameters	Δρmin = −0.35 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
C1	0.4333 (2)	0.7518 (2)	1.0256 (5)	0.0384 (8)
C2	0.3890 (2)	0.6623 (2)	1.0334 (4)	0.0379 (8)
C3	0.2979 (2)	0.6555 (2)	1.0813 (4)	0.0391 (8)
C4	0.2496 (2)	0.7362 (2)	1.1277 (4)	0.0399 (9)
C5	0.2918 (2)	0.8252 (2)	1.1218 (4)	0.0396 (8)
H5	0.2595	0.8796	1.1519	0.048*
C6	0.3819 (2)	0.8313 (2)	1.0709 (5)	0.0431 (9)
H6	0.4097	0.8909	1.0666	0.052*
C7	0.6747 (2)	0.8578 (2)	0.9220 (5)	0.0401 (9)
C8	0.7407 (3)	0.8069 (3)	1.0250 (5)	0.0504 (10)
H8	0.7216	0.7680	1.1170	0.060*
C9	0.8331 (3)	0.8129 (3)	0.9935 (5)	0.0562 (11)
H9	0.8758	0.7771	1.0621	0.067*
C10	0.8632 (2)	0.8713 (3)	0.8614 (6)	0.0486 (10)
C11	0.7995 (3)	0.9231 (3)	0.7578 (5)	0.0468 (9)
H11	0.8191	0.9628	0.6674	0.056*
C12	0.7062 (3)	0.9155 (2)	0.7898 (5)	0.0442 (9)
H12	0.6635	0.9506	0.7196	0.053*
C13	0.5738 (2)	0.8556 (3)	0.9633 (5)	0.0488 (10)
H13A	0.5397	0.8940	0.8743	0.059*
H13B	0.5672	0.8858	1.0789	0.059*
C14	0.5283 (2)	0.7592 (2)	0.9682 (4)	0.0398 (9)
C15	0.2723 (3)	0.5045 (3)	1.2103 (6)	0.0663 (12)
H15A	0.3383	0.4967	1.2260	0.100*
H15B	0.2441	0.4444	1.1807	0.100*
H15C	0.2483	0.5281	1.3194	0.100*
C16	0.1069 (3)	0.8046 (3)	1.2136 (6)	0.0631 (12)
H16A	0.1365	0.8398	1.3107	0.095*
H16B	0.0464	0.7849	1.2464	0.095*
H16C	0.1012	0.8440	1.1086	0.095*
C17	0.9921 (4)	0.9345 (4)	0.7095 (9)	0.101 (2)
H17A	0.9633	0.9206	0.5938	0.152*
H17B	1.0580	0.9260	0.7057	0.152*
H17C	0.9790	0.9991	0.7412	0.152*
O1	0.57164 (18)	0.68781 (18)	0.9225 (4)	0.0543 (8)
O2	0.4326 (2)	0.58075 (17)	0.9921 (4)	0.0499 (7)
O3	0.25205 (18)	0.56972 (17)	1.0703 (3)	0.0511 (7)
O4	0.16164 (17)	0.72248 (18)	1.1765 (4)	0.0517 (7)
O5	0.95673 (19)	0.8722 (2)	0.8396 (5)	0.0760 (10)
H18	0.489 (3)	0.597 (3)	0.960 (6)	0.063 (14)*

	U11	U22	U33	U12	U13	U23
C1	0.0403 (19)	0.0405 (19)	0.0339 (19)	0.0015 (16)	−0.0042 (15)	−0.0021 (15)
C2	0.050 (2)	0.0317 (18)	0.0310 (18)	0.0016 (15)	−0.0098 (15)	−0.0011 (14)
C3	0.046 (2)	0.0368 (19)	0.0338 (19)	−0.0040 (16)	−0.0085 (15)	0.0029 (15)
C4	0.040 (2)	0.045 (2)	0.0335 (19)	−0.0004 (16)	−0.0080 (15)	0.0018 (16)
C5	0.043 (2)	0.0360 (19)	0.040 (2)	0.0025 (15)	−0.0019 (16)	−0.0027 (15)
C6	0.053 (2)	0.0343 (19)	0.042 (2)	−0.0029 (16)	−0.0027 (17)	−0.0033 (16)
C7	0.045 (2)	0.0362 (18)	0.039 (2)	−0.0011 (16)	0.0019 (16)	−0.0038 (16)
C8	0.054 (2)	0.052 (2)	0.044 (2)	−0.0035 (19)	0.0015 (18)	0.0173 (18)
C9	0.052 (2)	0.058 (2)	0.057 (3)	0.0054 (19)	−0.0058 (19)	0.019 (2)
C10	0.041 (2)	0.040 (2)	0.066 (3)	0.0021 (17)	0.0118 (19)	0.0042 (19)
C11	0.055 (2)	0.040 (2)	0.046 (2)	0.0043 (18)	0.0107 (18)	0.0073 (17)
C12	0.053 (2)	0.0353 (19)	0.044 (2)	0.0051 (17)	−0.0011 (17)	0.0024 (16)
C13	0.046 (2)	0.045 (2)	0.056 (2)	−0.0046 (18)	0.0009 (18)	−0.0055 (19)
C14	0.046 (2)	0.042 (2)	0.0307 (19)	0.0023 (16)	−0.0067 (15)	−0.0015 (16)
C15	0.087 (3)	0.048 (2)	0.063 (3)	−0.012 (2)	−0.004 (2)	0.011 (2)
C16	0.045 (2)	0.063 (3)	0.081 (3)	0.006 (2)	0.001 (2)	−0.001 (2)
C17	0.065 (3)	0.081 (4)	0.162 (6)	0.008 (3)	0.047 (4)	0.047 (4)
O1	0.0498 (16)	0.0450 (15)	0.0682 (19)	−0.0002 (12)	0.0049 (13)	−0.0119 (13)
O2	0.0490 (17)	0.0357 (14)	0.0643 (18)	0.0020 (12)	−0.0038 (14)	−0.0076 (12)
O3	0.0600 (17)	0.0372 (14)	0.0544 (17)	−0.0103 (12)	−0.0131 (12)	0.0028 (12)
O4	0.0407 (15)	0.0497 (15)	0.0645 (18)	−0.0039 (12)	0.0017 (12)	−0.0010 (13)
O5	0.0485 (18)	0.075 (2)	0.106 (3)	0.0105 (16)	0.0207 (16)	0.0276 (19)

C1—C6	1.393 (5)	C11—C12	1.383 (5)
C1—C2	1.415 (5)	C11—H11	0.9300
C1—C14	1.461 (5)	C12—H12	0.9300
C2—O2	1.351 (4)	C13—C14	1.509 (5)
C2—C3	1.383 (5)	C13—H13A	0.9700
C3—O3	1.378 (4)	C13—H13B	0.9700
C3—C4	1.386 (5)	C14—O1	1.240 (4)
C4—O4	1.352 (4)	C15—O3	1.410 (5)
C4—C5	1.394 (5)	C15—H15A	0.9600
C5—C6	1.376 (5)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C6—H6	0.9300	C16—O4	1.434 (5)
C7—C12	1.372 (5)	C16—H16A	0.9600
C7—C8	1.393 (5)	C16—H16B	0.9600
C7—C13	1.505 (5)	C16—H16C	0.9600
C8—C9	1.368 (5)	C17—O5	1.422 (5)
C8—H8	0.9300	C17—H17A	0.9600
C9—C10	1.370 (5)	C17—H17B	0.9600
C9—H9	0.9300	C17—H17C	0.9600
C10—O5	1.368 (4)	O2—H18	0.89 (4)
C10—C11	1.380 (5)
C6—C1—C2	117.3 (3)	C7—C12—H12	119.0
C6—C1—C14	122.2 (3)	C11—C12—H12	119.0
C2—C1—C14	120.5 (3)	C7—C13—C14	116.8 (3)
O2—C2—C3	117.4 (3)	C7—C13—H13A	108.1
O2—C2—C1	122.1 (3)	C14—C13—H13A	108.1
C3—C2—C1	120.5 (3)	C7—C13—H13B	108.1
O3—C3—C2	120.3 (3)	C14—C13—H13B	108.1
O3—C3—C4	119.1 (3)	H13A—C13—H13B	107.3
C2—C3—C4	120.4 (3)	O1—C14—C1	121.1 (3)
O4—C4—C3	116.2 (3)	O1—C14—C13	119.8 (3)
O4—C4—C5	123.7 (3)	C1—C14—C13	119.1 (3)
C3—C4—C5	120.1 (3)	O3—C15—H15A	109.5
C6—C5—C4	119.0 (3)	O3—C15—H15B	109.5
C6—C5—H5	120.5	H15A—C15—H15B	109.5
C4—C5—H5	120.5	O3—C15—H15C	109.5
C5—C6—C1	122.6 (3)	H15A—C15—H15C	109.5
C5—C6—H6	118.7	H15B—C15—H15C	109.5
C1—C6—H6	118.7	O4—C16—H16A	109.5
C12—C7—C8	117.4 (3)	O4—C16—H16B	109.5
C12—C7—C13	121.2 (3)	H16A—C16—H16B	109.5
C8—C7—C13	121.3 (3)	O4—C16—H16C	109.5
C9—C8—C7	121.2 (3)	H16A—C16—H16C	109.5
C9—C8—H8	119.4	H16B—C16—H16C	109.5
C7—C8—H8	119.4	O5—C17—H17A	109.5
C8—C9—C10	120.5 (4)	O5—C17—H17B	109.5
C8—C9—H9	119.7	H17A—C17—H17B	109.5
C10—C9—H9	119.7	O5—C17—H17C	109.5
O5—C10—C9	116.2 (3)	H17A—C17—H17C	109.5
O5—C10—C11	124.2 (3)	H17B—C17—H17C	109.5
C9—C10—C11	119.6 (3)	C2—O2—H18	107 (3)
C10—C11—C12	119.3 (3)	C3—O3—C15	116.4 (3)
C10—C11—H11	120.3	C4—O4—C16	118.1 (3)
C12—C11—H11	120.3	C10—O5—C17	118.5 (3)
C7—C12—C11	122.0 (3)
C6—C1—C2—O2	180.0 (3)	C8—C9—C10—C11	−1.1 (6)
C14—C1—C2—O2	1.3 (5)	O5—C10—C11—C12	178.9 (4)
C6—C1—C2—C3	1.1 (5)	C9—C10—C11—C12	0.3 (6)
C14—C1—C2—C3	−177.6 (3)	C8—C7—C12—C11	0.4 (5)
O2—C2—C3—O3	−5.9 (5)	C13—C7—C12—C11	175.7 (3)
C1—C2—C3—O3	173.0 (3)	C10—C11—C12—C7	0.0 (6)
O2—C2—C3—C4	179.1 (3)	C12—C7—C13—C14	128.6 (4)
C1—C2—C3—C4	−2.0 (5)	C8—C7—C13—C14	−56.2 (5)
O3—C3—C4—O4	6.4 (4)	C6—C1—C14—O1	−177.5 (3)
C2—C3—C4—O4	−178.6 (3)	C2—C1—C14—O1	1.2 (5)
O3—C3—C4—C5	−173.4 (3)	C6—C1—C14—C13	2.0 (5)
C2—C3—C4—C5	1.7 (5)	C2—C1—C14—C13	−179.3 (3)
O4—C4—C5—C6	179.7 (3)	C7—C13—C14—O1	−6.7 (5)
C3—C4—C5—C6	−0.5 (5)	C7—C13—C14—C1	173.8 (3)
C4—C5—C6—C1	−0.3 (5)	C2—C3—O3—C15	78.6 (4)
C2—C1—C6—C5	0.0 (5)	C4—C3—O3—C15	−106.3 (4)
C14—C1—C6—C5	178.7 (3)	C3—C4—O4—C16	−175.8 (3)
C12—C7—C8—C9	−1.1 (6)	C5—C4—O4—C16	4.0 (5)
C13—C7—C8—C9	−176.5 (4)	C9—C10—O5—C17	−177.4 (4)
C7—C8—C9—C10	1.5 (6)	C11—C10—O5—C17	3.9 (6)
C8—C9—C10—O5	−179.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H18···O1	0.89 (4)	1.78 (4)	2.583 (4)	148 (4)
C15—H15A···O2	0.96	2.56	3.086 (5)	115
C11—H11···O3i	0.93	2.51	3.259 (4)	138
C17—H17B···O4ii	0.96	2.59	3.315 (6)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H18⋯O1	0.89 (4)	1.78 (4)	2.583 (4)	148 (4)
C15—H15A⋯O2	0.96	2.56	3.086 (5)	115
C11—H11⋯O3i	0.93	2.51	3.259 (4)	138
C17—H17B⋯O4ii	0.96	2.59	3.315 (6)	133

Symmetry codes: (i) ; (ii) .