1-(2-Hydr­oxy-3,4-dimethoxy­phen­yl)-2-(4-methoxy­phen­yl)ethanone

Xiao, Z.-P.; Xiao, H.-Y.

doi:10.1107/S1600536808036258

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2324

doi:10.1107/S1600536808036258

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1-(2-Hydroxy-3,4-dimethoxyphenyl)-2-(4-methoxyphenyl)ethanone

Zhu-Ping Xiao ^a ^* and He-Ying Xiao ^a

^aCollege of Chemistry & Chemical Engineering, Jishou University, Jishou 416000, People's Republic of China
^*Correspondence e-mail: xiaozhuping2005@163.com

(Received 19 October 2008; accepted 6 November 2008; online 13 November 2008)

In the title compound, C₁₇H₁₈O₅, 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 methoxy 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)°]. Intramolecular O—H⋯O and C—H⋯O hydrogen bonds help to establish the conformation, and the packing is consolidated by C—H⋯O interactions 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_r = 302.31
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.071
wR(F²) = 0.215
S = 1.03
2667 reflections
206 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.35 e Å⁻³

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) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x+1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036258/hb2823sup1.cif

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

checkCIF report

Comment top

Deoxybenzoins are intermediates in the synthesis of isoflavones (Xiao et al., 2008; Xiao, Fang et al., 2007) and found in several plants, such as Glycyrrhiza sp., Trifolium subterraneum and Ononis spinosa, and marine sources (Kiuchi et al., 1990; Niwa et al., 1999; Sanduja et al., 1985). Many of the deoxybenzoins have shown quite significant estrogen receptor modulatory, urease inhibitory, antimicrobial and antiviral properties (Papoutsi et al., 2007; Xiao, Shi et al., 2007; Parmar et al., 1996; Li et al., 2008). Consequently, we have synthesized a series of deoxybenzoins for bioactivity screen.

The bond lengths and angles of the title compound, (I), are unexceptional. The carbonyl group is almost coplanar with the pyrogallol fragment with a dihedral angle of 1.95 (13) °. The C16—O4—C4—C5 torsion angle [4.0 (5) °] indicates that the methoxy group is coplanar with the attached phenyl ring (pyrogallol fragment), the same as the methoxy group (O5, C17) attached to the p-methoxyphenyl moiety. However, the C15—O3—C3—C4 torsion angle indicates that the methoxy group is twisted at -106.3 (4) ° with respect to the pyrogallol ring.

The molecule of (I) is stabilized by intramolecular O—H···O and C—H···O hydrogen bonds (Table 1). The six-membered pseudo-ring closed by the former bond is almost planar with mean deviation of 0.010Å and coplanar with the fused C1—C6 benzene ring (Fig. 1). The packing is stabilized by intermolecular C—H···O hydrogen bonds as well as weak π-π interactions with a centroid-to-centroid distance of 3.735 (2)Å.

Related literature top

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 top

4-Methoxyphenacetyl chloride was prepared by treating 4-methoxyphenacetic acid with thionyl chloride at room temperature for 24 h. The solvent was removed in vacuo. To a mixture of pyrogallol trimethoxyl ether (2 g, 11.9 mmol) and 4-methoxyphenacetyl chloride (2.3 g, 12.2 mmol) in dried carbon disulfide (4 ml) was added anhydrous aluminium chloride (2.8 g) with stirring at room temperature overnight. Then the mixture was heated under reflux for 0.5 h. After removal of the solvent by decantation, the residue was poured into ice-cold diluted hydrochloric acid. The precipitate was suction filtered and crystallized from methanol to furnish light yellow blocks of (I).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 30% probability level.

1-(2-Hydroxy-3,4-dimethoxyphenyl)-2-(4-methoxyphenyl)ethanone top

Crystal data top

C₁₇H₁₈O₅	F(000) = 640
M_r = 302.31	D_x = 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 = 1.6–24.7°
b = 14.073 (3) Å	µ = 0.10 mm⁻¹
c = 7.4610 (15) Å	T = 293 K
β = 92.86 (3)°	Block, light-yellow
V = 1513.3 (5) Å³	0.30 × 0.30 × 0.30 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	2667 independent reflections
Radiation source: fine-focus sealed tube	1543 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
ω/2θ scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: ψ scan (North et al., 1968)	h = −17→17
T_min = 0.971, T_max = 0.971	k = −16→0
2893 measured reflections	l = 0→8

Refinement top

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)] = 0.071	Hydrogen site location: difmap and geom
wR(F²) = 0.215	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.1231P)²] where P = (F_o² + 2F_c²)/3
2667 reflections	(Δ/σ)_max < 0.001
206 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₇H₁₈O₅	V = 1513.3 (5) Å³
M_r = 302.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.431 (3) Å	µ = 0.10 mm⁻¹
b = 14.073 (3) Å	T = 293 K
c = 7.4610 (15) Å	0.30 × 0.30 × 0.30 mm
β = 92.86 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2667 independent reflections
Absorption correction: ψ scan (North et al., 1968)	1543 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.971	R_int = 0.059
2893 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	0 restraints
wR(F²) = 0.215	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.28 e Å⁻³
2667 reflections	Δρ_min = −0.35 e Å⁻³
206 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y+1/2, −z+3/2; (ii) x+1, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈O₅
M_r	302.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	14.431 (3), 14.073 (3), 7.4610 (15)
β (°)	92.86 (3)
V (Å³)	1513.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.30 × 0.30

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.971, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	2893, 2667, 1543
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.215, 1.03
No. of reflections	2667
No. of parameters	206
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.35

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+1, y+1/2, −z+3/2; (ii) x+1, −y+3/2, z−1/2.

Acknowledgements

The work was financed by a grant (No. JDKYZZ0801) from Jishou University for talent introduction, China.

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