(E)-3-(3,5-Dimeth­oxy­phen­yl)-1-(1-hy­droxy­naphthalen-2-yl)prop-2-en-1-one

Lee, H.-J.; Lim, Y.; Koh, D.

doi:10.1107/S1600536812046715

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3403

doi:10.1107/S1600536812046715

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(E)-3-(3,5-Dimethoxyphenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one

Ha-Jin Lee,^a Yoongho Lim ^b and Dongsoo Koh ^c ^*

^aJeonju Center, Korea Basic Science Center (KBSI), Jeonju 561-765, Republic of Korea, ^bDivision of Bioscience and Biotechnology, BMIC, Konkuk University, Seoul 143-701, Republic of Korea, and ^cDepartment of Applied Chemistry, Dongduk Women's University, Seoul 136-714, Republic of Korea
^*Correspondence e-mail: dskoh@dongduk.ac.kr

(Received 5 November 2012; accepted 13 November 2012; online 24 November 2012)

In the title molecule, C₂₁H₁₈O₄, the C=C bond of the central enone group adopts a trans conformation. The dihedral angle formed by the naphthalene ring system and the benzene ring is 2.97 (11)°. The hydroxy group is involved in an intramolecular O—H⋯O hydrogen bond. In the crystal, weak C—H⋯O hydrogen bonds link the molecules into chains along [001].

Related literature

For the synthesis and biological properties of chalcone derivatives, see: Sharma et al. (2012 ); Singh et al. (2012 ); Bandgar et al. (2010 ); Hans et al. (2010 ); Hwang et al. (2011 ). For related structures, see: Fadzillah et al. (2012 ); Jasinski et al. (2011 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₁H₁₈O₄
M_r = 334.35
Orthorhombic, P n a 2₁
a = 30.179 (3) Å
b = 3.9127 (3) Å
c = 13.7363 (12) Å
V = 1622.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 200 K
0.24 × 0.22 × 0.17 mm

Data collection

Bruker SMART CCD diffractometer
11095 measured reflections
3479 independent reflections
1828 reflections with I > 2σ(I)
R_int = 0.064

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.102
S = 0.94
3479 reflections
229 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O1	0.84	1.75	2.503 (3)	147
C7—H7C⋯O1ⁱ	0.98	2.59	3.157 (4)	117
C10—H10B⋯O2ⁱ	0.98	2.54	3.344 (4)	139
Symmetry code: (i) $[-x+1, -y+3, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812046715/lh5555sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812046715/lh5555Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812046715/lh5555Isup3.cml

checkCIF report

Comment top

Chalcones are one of the secondary metabolites in plants and belong to a flavonoid class with a C6—C3—C6 skeleton and C3 skeleton which is an α,β-unsaturated carbonyl (enone) group. Because of their diverse biological activities including anticancer (Singh et al., 2012), anti-inflammatory (Bandgar et al., 2010), anti-tubercular (Hans et al., 2010), and antimicrobial (Sharma et al., 2012), various chlacones have been isolated from natural sources and syntheized. In continuation of our research to develop novel chalcone derivatives which show broad range of biological activities (Hwang et al., 2011) the title compound was synthesized and and its crystal structure was determined.

The molecular structure of the title compound is shown in Fig .1. The C2═C3 bond of the central enone group adopts a trans configuration. The dihedral angle formed by the naphthalene ring system and the benzene ring is 2.97 (11)°. The C1═O1 bond [1.242 (3) Å] is slightly longer than the standard value (Allen et al. 1987) as this group is involved in an intramolecular O—H···O hydrogen bond with the hydroxy group. In the crystal, weak C—H···O hydrogen bonds link the molecules into one-dimensional chains along [001] (Fig. 2). Examples of structures of substituted prop-2-en-1-one compounds have been published (Fadzillah et al., 2012; Jasinski et al., 2011).

Related literature top

For the synthesis and biological properties of chalcone derivatives, see: Sharma et al. (2012); Singh et al. (2012); Bandgar et al. (2010); Hans et al. (2010); Hwang et al. (2011). For related structures, see: Fadzillah et al. (2012); Jasinski et al. (2011). For standard bond lengths, see: Allen et al. (1987).

Experimental top

A solution of 1-hydroxy-2-acetonaphthone (186 mg, 1 mmol) and 3,5-dimethoxybenzaldehyde (166 mg, 1 mmol) was dissolved in 10 ml of ethanol and the temperature was adjusted to around 276-277K in an ice-bath. To the cooled reaction mixture was added 0.5 ml of 50% aqueous KOH solution, and the reaction mixture was stirred at room temperature for 24 h. This mixture was poured into iced water (20 ml) was acidified with 6 N HCl solution. The mixture was extracted with ethylacetate (3 × 20 ml) and the combined organic layers were dried under MgSO₄. Filtration and evaporation of the filtrate gave a residue which was purified by flash chromatography to give the title compound (210 mg, 63%). Recrystallization of the title compound in ethanol gave orange colored crystals (mp: 422-424K).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level. The dashed line indicates a hydrogen bond.
	Fig. 2. Part of the crystal structure with weak intermolecular C—H···O hydrogen bonds shown as dashed lines.

(E)-3-(3,5-Dimethoxyphenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one top

Crystal data top

C₂₁H₁₈O₄	F(000) = 704
M_r = 334.35	D_x = 1.369 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2578 reflections
a = 30.179 (3) Å	θ = 2.7–27.8°
b = 3.9127 (3) Å	µ = 0.09 mm⁻¹
c = 13.7363 (12) Å	T = 200 K
V = 1622.0 (2) Å³	Block, orange
Z = 4	0.24 × 0.22 × 0.17 mm

Data collection top

Bruker SMART CCD diffractometer	1828 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.064
Graphite monochromator	θ_max = 28.3°, θ_min = 1.4°
ϕ and ω scans	h = −32→40
11095 measured reflections	k = −5→5
3479 independent reflections	l = −16→18

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0276P)²] where P = (F_o² + 2F_c²)/3
3479 reflections	(Δ/σ)_max < 0.001
229 parameters	Δρ_max = 0.22 e Å⁻³
1 restraint	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₁H₁₈O₄	V = 1622.0 (2) Å³
M_r = 334.35	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 30.179 (3) Å	µ = 0.09 mm⁻¹
b = 3.9127 (3) Å	T = 200 K
c = 13.7363 (12) Å	0.24 × 0.22 × 0.17 mm

Data collection top

Bruker SMART CCD diffractometer	1828 reflections with I > 2σ(I)
11095 measured reflections	R_int = 0.064
3479 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	1 restraint
wR(F²) = 0.102	H-atom parameters constrained
S = 0.94	Δρ_max = 0.22 e Å⁻³
3479 reflections	Δρ_min = −0.23 e Å⁻³
229 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	0.35700 (10)	0.8619 (7)	0.4892 (2)	0.0348 (7)
O1	0.36736 (7)	0.9296 (6)	0.57454 (14)	0.0485 (6)
C2	0.38738 (10)	0.9586 (8)	0.4096 (2)	0.0362 (8)
H2	0.3791	0.9009	0.3449	0.043*
C3	0.42532 (10)	1.1203 (7)	0.4228 (2)	0.0352 (7)
H3	0.4326	1.1809	0.4878	0.042*
C4	0.45715 (10)	1.2153 (7)	0.3474 (2)	0.0312 (7)
C5	0.49588 (10)	1.3745 (7)	0.3726 (2)	0.0340 (7)
H5	0.5011	1.4326	0.4388	0.041*
C6	0.52799 (10)	1.4530 (7)	0.3019 (2)	0.0335 (8)
O2	0.56629 (7)	1.5970 (6)	0.33591 (14)	0.0424 (6)
C7	0.59853 (11)	1.7037 (8)	0.2650 (2)	0.0420 (9)
H7A	0.6101	1.5029	0.2307	0.063*
H7B	0.6229	1.8220	0.2979	0.063*
H7C	0.5846	1.8587	0.2182	0.063*
C8	0.52006 (10)	1.3789 (7)	0.2050 (2)	0.0334 (7)
H8	0.5414	1.4332	0.1565	0.040*
C9	0.48010 (10)	1.2229 (7)	0.1799 (2)	0.0322 (7)
O3	0.47555 (7)	1.1594 (5)	0.08193 (15)	0.0416 (5)
C10	0.43530 (10)	1.0023 (8)	0.0509 (2)	0.0428 (8)
H10A	0.4337	0.7696	0.0771	0.064*
H10B	0.4345	0.9936	−0.0204	0.064*
H10C	0.4100	1.1357	0.0746	0.064*
C11	0.44877 (10)	1.1405 (7)	0.2483 (2)	0.0343 (8)
H11	0.4218	1.0346	0.2293	0.041*
C12	0.31508 (10)	0.6927 (7)	0.4670 (2)	0.0290 (7)
C13	0.28636 (10)	0.6041 (8)	0.5424 (2)	0.0319 (7)
O4	0.29656 (7)	0.6743 (6)	0.63545 (14)	0.0437 (6)
H4	0.3204	0.7843	0.6375	0.066*
C14	0.24525 (10)	0.4418 (7)	0.5241 (2)	0.0311 (7)
C15	0.21607 (10)	0.3500 (8)	0.6006 (2)	0.0377 (8)
H15	0.2241	0.3941	0.6663	0.045*
C16	0.17643 (10)	0.1979 (8)	0.5797 (2)	0.0408 (8)
H16	0.1568	0.1392	0.6311	0.049*
C17	0.16454 (10)	0.1281 (8)	0.4837 (2)	0.0398 (8)
H17	0.1368	0.0242	0.4702	0.048*
C18	0.19236 (11)	0.2075 (8)	0.4093 (2)	0.0366 (8)
H18	0.1841	0.1533	0.3444	0.044*
C19	0.23315 (10)	0.3683 (7)	0.4268 (2)	0.0293 (7)
C20	0.26243 (10)	0.4564 (7)	0.3506 (2)	0.0360 (8)
H20	0.2545	0.4061	0.2852	0.043*
C21	0.30156 (10)	0.6117 (8)	0.3696 (2)	0.0351 (8)
H21	0.3206	0.6686	0.3170	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0311 (19)	0.0388 (19)	0.0344 (19)	−0.0019 (15)	−0.0011 (14)	0.0023 (16)
O1	0.0434 (15)	0.0720 (17)	0.0302 (13)	−0.0130 (12)	−0.0004 (10)	−0.0007 (12)
C2	0.0288 (19)	0.049 (2)	0.0312 (18)	−0.0061 (15)	0.0035 (13)	−0.0010 (15)
C3	0.035 (2)	0.0414 (19)	0.0297 (16)	−0.0024 (16)	−0.0001 (15)	0.0006 (16)
C4	0.0289 (18)	0.0324 (18)	0.0324 (18)	0.0014 (14)	−0.0023 (14)	0.0011 (14)
C5	0.0316 (19)	0.0379 (19)	0.0324 (17)	−0.0025 (15)	0.0020 (14)	0.0014 (15)
C6	0.0286 (19)	0.0322 (18)	0.0396 (19)	−0.0001 (14)	−0.0033 (14)	0.0036 (15)
O2	0.0314 (13)	0.0531 (14)	0.0428 (14)	−0.0114 (11)	−0.0010 (11)	0.0022 (11)
C7	0.031 (2)	0.043 (2)	0.052 (2)	−0.0077 (16)	0.0043 (16)	0.0082 (17)
C8	0.0286 (19)	0.0368 (18)	0.0348 (18)	−0.0012 (14)	0.0022 (14)	0.0004 (15)
C9	0.0363 (19)	0.0325 (17)	0.0279 (18)	0.0032 (14)	−0.0055 (14)	0.0035 (14)
O3	0.0376 (14)	0.0555 (15)	0.0316 (12)	−0.0060 (11)	−0.0007 (10)	−0.0017 (11)
C10	0.042 (2)	0.049 (2)	0.0380 (19)	−0.0040 (17)	−0.0094 (15)	−0.0001 (15)
C11	0.0290 (19)	0.040 (2)	0.0342 (18)	−0.0053 (15)	0.0003 (14)	0.0021 (15)
C12	0.0258 (18)	0.0345 (18)	0.0266 (16)	−0.0016 (14)	−0.0005 (13)	0.0018 (14)
C13	0.0304 (19)	0.0373 (18)	0.0281 (17)	−0.0001 (14)	0.0012 (14)	−0.0002 (15)
O4	0.0414 (16)	0.0659 (16)	0.0237 (12)	−0.0129 (12)	−0.0014 (10)	−0.0015 (11)
C14	0.0303 (19)	0.0304 (16)	0.0326 (18)	0.0000 (14)	0.0012 (13)	0.0024 (14)
C15	0.036 (2)	0.045 (2)	0.0329 (19)	−0.0040 (15)	0.0036 (14)	0.0042 (15)
C16	0.035 (2)	0.045 (2)	0.042 (2)	−0.0020 (16)	0.0060 (16)	0.0032 (17)
C17	0.029 (2)	0.0414 (19)	0.049 (2)	−0.0073 (15)	0.0001 (16)	−0.0013 (17)
C18	0.034 (2)	0.038 (2)	0.0383 (19)	−0.0013 (15)	−0.0026 (14)	0.0020 (15)
C19	0.0282 (18)	0.0269 (16)	0.0329 (16)	−0.0012 (13)	0.0003 (14)	0.0009 (14)
C20	0.035 (2)	0.0434 (19)	0.0293 (17)	−0.0006 (15)	−0.0047 (14)	−0.0002 (15)
C21	0.0327 (19)	0.045 (2)	0.0279 (17)	−0.0018 (15)	0.0016 (14)	0.0014 (15)

Geometric parameters (Å, º) top

C1—O1	1.242 (3)	C10—H10B	0.9800
C1—C12	1.460 (4)	C10—H10C	0.9800
C1—C2	1.476 (4)	C11—H11	0.9500
C2—C3	1.321 (4)	C12—C13	1.395 (4)
C2—H2	0.9500	C12—C21	1.433 (4)
C3—C4	1.460 (4)	C13—O4	1.343 (3)
C3—H3	0.9500	C13—C14	1.416 (4)
C4—C5	1.369 (4)	O4—H4	0.8400
C4—C11	1.416 (4)	C14—C19	1.414 (4)
C5—C6	1.406 (4)	C14—C15	1.418 (4)
C5—H5	0.9500	C15—C16	1.367 (4)
C6—O2	1.368 (3)	C15—H15	0.9500
C6—C8	1.384 (4)	C16—C17	1.394 (4)
O2—C7	1.438 (3)	C16—H16	0.9500
C7—H7A	0.9800	C17—C18	1.359 (4)
C7—H7B	0.9800	C17—H17	0.9500
C7—H7C	0.9800	C18—C19	1.403 (4)
C8—C9	1.395 (4)	C18—H18	0.9500
C8—H8	0.9500	C19—C20	1.413 (4)
C9—C11	1.371 (4)	C20—C21	1.354 (4)
C9—O3	1.375 (3)	C20—H20	0.9500
O3—C10	1.427 (3)	C21—H21	0.9500
C10—H10A	0.9800

O1—C1—C12	120.8 (3)	H10A—C10—H10C	109.5
O1—C1—C2	119.2 (3)	H10B—C10—H10C	109.5
C12—C1—C2	120.0 (3)	C9—C11—C4	119.2 (3)
C3—C2—C1	124.1 (3)	C9—C11—H11	120.4
C3—C2—H2	118.0	C4—C11—H11	120.4
C1—C2—H2	118.0	C13—C12—C21	117.5 (3)
C2—C3—C4	126.5 (3)	C13—C12—C1	119.7 (3)
C2—C3—H3	116.7	C21—C12—C1	122.8 (3)
C4—C3—H3	116.7	O4—C13—C12	120.9 (3)
C5—C4—C11	119.3 (3)	O4—C13—C14	117.5 (2)
C5—C4—C3	119.9 (3)	C12—C13—C14	121.6 (3)
C11—C4—C3	120.8 (3)	C13—O4—H4	109.5
C4—C5—C6	120.9 (3)	C19—C14—C13	119.0 (3)
C4—C5—H5	119.6	C19—C14—C15	119.2 (3)
C6—C5—H5	119.6	C13—C14—C15	121.7 (3)
O2—C6—C8	124.1 (3)	C16—C15—C14	119.9 (3)
O2—C6—C5	115.9 (3)	C16—C15—H15	120.0
C8—C6—C5	120.0 (3)	C14—C15—H15	120.0
C6—O2—C7	117.4 (2)	C15—C16—C17	120.6 (3)
O2—C7—H7A	109.5	C15—C16—H16	119.7
O2—C7—H7B	109.5	C17—C16—H16	119.7
H7A—C7—H7B	109.5	C18—C17—C16	120.5 (3)
O2—C7—H7C	109.5	C18—C17—H17	119.7
H7A—C7—H7C	109.5	C16—C17—H17	119.7
H7B—C7—H7C	109.5	C17—C18—C19	121.0 (3)
C6—C8—C9	118.6 (3)	C17—C18—H18	119.5
C6—C8—H8	120.7	C19—C18—H18	119.5
C9—C8—H8	120.7	C18—C19—C20	122.0 (3)
C11—C9—O3	124.0 (3)	C18—C19—C14	118.7 (3)
C11—C9—C8	122.0 (3)	C20—C19—C14	119.3 (3)
O3—C9—C8	114.0 (3)	C21—C20—C19	120.8 (3)
C9—O3—C10	117.1 (2)	C21—C20—H20	119.6
O3—C10—H10A	109.5	C19—C20—H20	119.6
O3—C10—H10B	109.5	C20—C21—C12	121.9 (3)
H10A—C10—H10B	109.5	C20—C21—H21	119.1
O3—C10—H10C	109.5	C12—C21—H21	119.1

O1—C1—C2—C3	−1.1 (5)	C21—C12—C13—O4	−179.4 (3)
C12—C1—C2—C3	178.1 (3)	C1—C12—C13—O4	0.5 (4)
C1—C2—C3—C4	178.4 (3)	C21—C12—C13—C14	−0.3 (4)
C2—C3—C4—C5	−178.1 (3)	C1—C12—C13—C14	179.6 (3)
C2—C3—C4—C11	1.0 (5)	O4—C13—C14—C19	179.1 (3)
C11—C4—C5—C6	−2.3 (5)	C12—C13—C14—C19	0.0 (4)
C3—C4—C5—C6	176.8 (3)	O4—C13—C14—C15	−1.2 (4)
C4—C5—C6—O2	−177.0 (3)	C12—C13—C14—C15	179.7 (3)
C4—C5—C6—C8	2.0 (4)	C19—C14—C15—C16	−1.2 (5)
C8—C6—O2—C7	5.5 (4)	C13—C14—C15—C16	179.1 (3)
C5—C6—O2—C7	−175.6 (3)	C14—C15—C16—C17	0.8 (5)
O2—C6—C8—C9	178.2 (3)	C15—C16—C17—C18	0.6 (5)
C5—C6—C8—C9	−0.7 (4)	C16—C17—C18—C19	−1.5 (5)
C6—C8—C9—C11	−0.3 (4)	C17—C18—C19—C20	−179.3 (3)
C6—C8—C9—O3	−179.8 (3)	C17—C18—C19—C14	1.0 (4)
C11—C9—O3—C10	0.9 (4)	C13—C14—C19—C18	180.0 (3)
C8—C9—O3—C10	−179.6 (2)	C15—C14—C19—C18	0.3 (4)
O3—C9—C11—C4	179.4 (3)	C13—C14—C19—C20	0.4 (4)
C8—C9—C11—C4	−0.1 (4)	C15—C14—C19—C20	−179.3 (3)
C5—C4—C11—C9	1.3 (5)	C18—C19—C20—C21	179.9 (3)
C3—C4—C11—C9	−177.8 (3)	C14—C19—C20—C21	−0.4 (4)
O1—C1—C12—C13	−0.4 (4)	C19—C20—C21—C12	0.1 (4)
C2—C1—C12—C13	−179.6 (3)	C13—C12—C21—C20	0.3 (4)
O1—C1—C12—C21	179.5 (3)	C1—C12—C21—C20	−179.6 (3)
C2—C1—C12—C21	0.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O1	0.84	1.75	2.503 (3)	147
C7—H7C···O1ⁱ	0.98	2.59	3.157 (4)	117
C10—H10B···O2ⁱ	0.98	2.54	3.344 (4)	139

Symmetry code: (i) −x+1, −y+3, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₈O₄
M_r	334.35
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	200
a, b, c (Å)	30.179 (3), 3.9127 (3), 13.7363 (12)
V (Å³)	1622.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.24 × 0.22 × 0.17

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11095, 3479, 1828
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.102, 0.94
No. of reflections	3479
No. of parameters	229
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.23

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O1	0.84	1.75	2.503 (3)	147
C7—H7C···O1ⁱ	0.98	2.59	3.157 (4)	117.3
C10—H10B···O2ⁱ	0.98	2.54	3.344 (4)	138.9

Symmetry code: (i) −x+1, −y+3, z−1/2.

References

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Volume 68| Part 12| December 2012| Page o3403

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