4-But­oxy-3-(2,4-dichloro­phen­yl)-1-oxaspiro­[4.5]dec-3-en-2-one

Xu, L.; Sun, S.; Guo, W.; Su, Q.

doi:10.1107/S1600536809000579

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o302

doi:10.1107/S1600536809000579

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4-Butoxy-3-(2,4-dichlorophenyl)-1-oxaspiro[4.5]dec-3-en-2-one

Liang-zhong Xu,^a ^* Shan-qi Sun,^a Wei Guo ^a and Qun-qun Su ^a

^aCollege of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China
^*Correspondence e-mail: qknhs@yahoo.com.cn

(Received 16 December 2008; accepted 7 January 2009; online 14 January 2009)

In the title compound, C₁₉H₂₂Cl₂O₃, the cyclohexane ring adopts a chair conformation. The furan ring plane forms dihedral angles of 81.88 (2) and 50.19 (3)°, respectively, with the benzene ring and the plane formed by the butyl C atoms. The crystal structure is stabilized by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For the biological activity of related compounds, see: Thomas et al. (2003 ). For synthetic information, see: Raeppel et al. (1998 ); Sarcevic et al. (1973 ).

Experimental

Crystal data

C₁₉H₂₂Cl₂O₃
M_r = 369.27
Orthorhombic, P b c a
a = 15.177 (3) Å
b = 13.735 (3) Å
c = 17.497 (4) Å
V = 3647.4 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 113 (2) K
0.18 × 0.14 × 0.10 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.936, T_max = 0.964
23387 measured reflections
3217 independent reflections
2536 reflections with I > 2σ(I)
R_int = 0.090

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.131
S = 1.08
3217 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.60 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
C2—H2B⋯O2ⁱ	0.97	2.54	3.316 (3)	137
C18—H18⋯O1ⁱⁱ	0.93	2.49	3.370 (3)	159
Symmetry codes: (i) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000579/lh2747sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809000579/lh2747Isup2.hkl

checkCIF report

Comment top

The title compound (I) was prepared as part of a project in search for new compounds with biological activity (Thomas et al., 2003). We report here the crystal structure of (I).

In (I) (Fig. 1), all bond lengths and angles are normal and in a good agreement with those reported previously (Thomas et al., 2003). The cyclohexane ring (C1—C6) adopts a chair conformation. The furan ring (O1/C1/C7/C12/C13) plane forms dihedral angles of 81.88 (2)° and 50.19 (3)° with the benzene ring (C14—C19) and the butyl group plane (C8—C11) respectively. In addition to van der Waals forces, the structure is stabilized by weak C—H···O hydrogen bonds.

Related literature top

For the biological activity of related compounds, see: Thomas et al. (2003). For synthetic information, see: Raeppel et al. (1998); Sarcevic et al. (1973).

Experimental top

3-(2,4-Dichlorophenyl)-2,4-dioxo-1-oxaspiro[4.5]decane 3.13 g (10.0 mmol), was suspended in a solution of sodium carbonate 0.54 g (5.1 mmol) in 20 ml of water in a flask equipped with stirrer, water separator and reflux condenser. Toluene (40 ml) was added after 0.5 h, the mixture was heated to dehydration to distill the toluene solvent. Then 1-bromobutane 1.51 g (11.0 mmol) and N,N-dimethylformamide(DMF) solvent (20 ml) were added while maintaining the temperature at 373K for 4 h. Upon cooling at room temperature water (20 ml) was added. The mixture was extracted with CH₂Cl₂ (15 ml) and the organic layer was washed with water and dried over sodium sulfate. The excess CH₂Cl₂ was removed on a water vacuum pump to obtain the oily product which was crystallized from methanol to afford the title compound 2.95 g (80% yield) (Raeppel et al., 1998; Sarcevic et al., 1973). Single crystals suitable for X-ray diffraction were obtained by recrystallization of the title compound from a mixture of acetone and methanol at room temperature.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 drawn at the 40% probability level.

4-Butoxy-3-(2,4-dichlorophenyl)-1-oxaspiro[4.5]dec-3-en-2-one top

Crystal data top

C₁₉H₂₂Cl₂O₃	F(000) = 1552
M_r = 369.27	D_x = 1.345 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7182 reflections
a = 15.177 (3) Å	θ = 2.3–27.5°
b = 13.735 (3) Å	µ = 0.37 mm⁻¹
c = 17.497 (4) Å	T = 113 K
V = 3647.4 (13) Å³	Platelet, colorless
Z = 8	0.18 × 0.14 × 0.10 mm

Data collection top

Rigaku Saturn diffractometer	3217 independent reflections
Radiation source: rotating anode	2536 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.090
ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −17→18
T_min = 0.936, T_max = 0.964	k = −16→13
23387 measured reflections	l = −20→19

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0705P)² + 0.1293P] where P = (F_o² + 2F_c²)/3
3217 reflections	(Δ/σ)_max = 0.001
218 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₉H₂₂Cl₂O₃	V = 3647.4 (13) Å³
M_r = 369.27	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 15.177 (3) Å	µ = 0.37 mm⁻¹
b = 13.735 (3) Å	T = 113 K
c = 17.497 (4) Å	0.18 × 0.14 × 0.10 mm

Data collection top

Rigaku Saturn diffractometer	3217 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2536 reflections with I > 2σ(I)
T_min = 0.936, T_max = 0.964	R_int = 0.090
23387 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.08	Δρ_max = 0.60 e Å⁻³
3217 reflections	Δρ_min = −0.35 e Å⁻³
218 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
Cl1	0.10283 (4)	0.81909 (5)	0.06309 (3)	0.0362 (2)
Cl2	−0.13817 (4)	0.55405 (6)	−0.02124 (4)	0.0402 (2)
O1	0.12744 (9)	0.83740 (13)	0.31227 (8)	0.0267 (4)
O2	−0.00361 (10)	0.84602 (15)	0.25290 (10)	0.0382 (5)
O3	0.24825 (9)	0.64650 (13)	0.22585 (8)	0.0234 (4)
C1	0.20839 (12)	0.78176 (19)	0.30321 (12)	0.0211 (5)
C2	0.28018 (14)	0.84967 (19)	0.27409 (13)	0.0244 (5)
H2A	0.2608	0.8795	0.2267	0.029*
H2B	0.3328	0.8120	0.2632	0.029*
C3	0.30279 (14)	0.9295 (2)	0.33171 (13)	0.0299 (6)
H3A	0.3507	0.9690	0.3121	0.036*
H3B	0.2521	0.9714	0.3391	0.036*
C4	0.32958 (15)	0.8847 (2)	0.40787 (13)	0.0323 (6)
H4A	0.3401	0.9362	0.4447	0.039*
H4B	0.3841	0.8489	0.4014	0.039*
C5	0.25880 (15)	0.8165 (2)	0.43855 (13)	0.0307 (6)
H5A	0.2067	0.8540	0.4513	0.037*
H5B	0.2799	0.7859	0.4850	0.037*
C6	0.23407 (14)	0.7375 (2)	0.38050 (12)	0.0259 (6)
H6A	0.1851	0.6997	0.4002	0.031*
H6B	0.2837	0.6938	0.3735	0.031*
C7	0.18423 (13)	0.70785 (18)	0.24397 (12)	0.0195 (5)
C8	0.23904 (13)	0.58949 (18)	0.15675 (12)	0.0225 (5)
H8A	0.2200	0.6304	0.1147	0.027*
H8B	0.1959	0.5382	0.1640	0.027*
C9	0.32863 (14)	0.54638 (17)	0.13996 (13)	0.0241 (5)
H9A	0.3247	0.5073	0.0939	0.029*
H9B	0.3450	0.5035	0.1816	0.029*
C10	0.40051 (13)	0.6221 (2)	0.12948 (13)	0.0275 (6)
H10A	0.4078	0.6583	0.1767	0.033*
H10B	0.3829	0.6677	0.0899	0.033*
C11	0.48797 (15)	0.5757 (2)	0.10750 (14)	0.0380 (7)
H11A	0.5013	0.5239	0.1425	0.057*
H11B	0.5338	0.6238	0.1096	0.057*
H11C	0.4840	0.5501	0.0566	0.057*
C12	0.10200 (13)	0.72226 (19)	0.21741 (12)	0.0204 (5)
C13	0.06647 (13)	0.80578 (19)	0.25970 (12)	0.0255 (6)
C14	0.04851 (13)	0.67432 (18)	0.15677 (12)	0.0207 (5)
C15	0.04096 (13)	0.71635 (18)	0.08456 (12)	0.0229 (5)
C16	−0.01452 (14)	0.67937 (18)	0.02864 (12)	0.0257 (5)
H16	−0.0185	0.7085	−0.0192	0.031*
C17	−0.06371 (14)	0.59783 (19)	0.04641 (13)	0.0267 (6)
C18	−0.05625 (14)	0.5511 (2)	0.11608 (13)	0.0285 (6)
H18	−0.0881	0.4947	0.1262	0.034*
C19	−0.00021 (13)	0.59027 (18)	0.17061 (12)	0.0240 (5)
H19	0.0050	0.5595	0.2178	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0475 (4)	0.0282 (4)	0.0329 (4)	−0.0146 (3)	−0.0045 (3)	0.0049 (3)
Cl2	0.0339 (3)	0.0451 (5)	0.0417 (4)	−0.0047 (3)	−0.0147 (3)	−0.0141 (3)
O1	0.0154 (7)	0.0332 (11)	0.0316 (9)	0.0046 (7)	−0.0038 (6)	−0.0143 (8)
O2	0.0195 (8)	0.0453 (13)	0.0499 (11)	0.0089 (8)	−0.0087 (7)	−0.0205 (10)
O3	0.0208 (7)	0.0267 (10)	0.0229 (8)	0.0088 (7)	−0.0027 (6)	−0.0074 (7)
C1	0.0151 (9)	0.0250 (13)	0.0231 (11)	0.0041 (11)	−0.0005 (8)	−0.0033 (10)
C2	0.0188 (10)	0.0277 (14)	0.0269 (12)	−0.0003 (11)	−0.0027 (8)	0.0018 (11)
C3	0.0214 (11)	0.0281 (14)	0.0402 (14)	−0.0038 (11)	−0.0049 (9)	−0.0051 (12)
C4	0.0254 (11)	0.0382 (16)	0.0334 (12)	−0.0002 (12)	−0.0081 (10)	−0.0073 (12)
C5	0.0309 (12)	0.0395 (16)	0.0215 (12)	0.0013 (12)	−0.0045 (9)	−0.0062 (11)
C6	0.0252 (11)	0.0301 (15)	0.0224 (11)	−0.0021 (11)	0.0006 (8)	−0.0013 (11)
C7	0.0180 (10)	0.0211 (12)	0.0195 (10)	0.0015 (11)	0.0022 (8)	0.0001 (9)
C8	0.0202 (10)	0.0250 (14)	0.0224 (11)	0.0031 (10)	−0.0031 (8)	−0.0061 (10)
C9	0.0232 (11)	0.0238 (13)	0.0254 (11)	0.0027 (11)	0.0010 (8)	−0.0069 (10)
C10	0.0255 (11)	0.0309 (15)	0.0259 (11)	0.0015 (12)	−0.0007 (9)	0.0018 (11)
C11	0.0247 (11)	0.062 (2)	0.0269 (12)	−0.0027 (14)	0.0036 (9)	−0.0034 (13)
C12	0.0186 (10)	0.0220 (13)	0.0206 (11)	0.0014 (11)	−0.0015 (8)	−0.0020 (10)
C13	0.0142 (10)	0.0326 (15)	0.0298 (12)	−0.0007 (11)	−0.0032 (8)	−0.0091 (11)
C14	0.0149 (9)	0.0240 (12)	0.0231 (11)	0.0029 (10)	−0.0006 (8)	−0.0048 (10)
C15	0.0198 (9)	0.0206 (12)	0.0284 (11)	−0.0028 (11)	−0.0005 (8)	−0.0025 (10)
C16	0.0289 (11)	0.0248 (14)	0.0233 (12)	0.0042 (11)	−0.0053 (9)	−0.0012 (10)
C17	0.0201 (10)	0.0293 (14)	0.0307 (12)	−0.0009 (11)	−0.0050 (9)	−0.0106 (11)
C18	0.0224 (11)	0.0292 (14)	0.0340 (13)	−0.0060 (11)	0.0004 (9)	−0.0034 (11)
C19	0.0214 (10)	0.0268 (14)	0.0239 (11)	−0.0031 (11)	0.0011 (8)	0.0013 (10)

Geometric parameters (Å, º) top

Cl1—C15	1.736 (2)	C7—C12	1.346 (3)
Cl2—C17	1.744 (2)	C8—C9	1.512 (3)
O1—C13	1.375 (3)	C8—H8A	0.9700
O1—C1	1.455 (2)	C8—H8B	0.9700
O2—C13	1.204 (3)	C9—C10	1.519 (3)
O3—C7	1.325 (3)	C9—H9A	0.9700
O3—C8	1.447 (3)	C9—H9B	0.9700
C1—C7	1.497 (3)	C10—C11	1.522 (3)
C1—C2	1.522 (3)	C10—H10A	0.9700
C1—C6	1.533 (3)	C10—H10B	0.9700
C2—C3	1.529 (3)	C11—H11A	0.9600
C2—H2A	0.9700	C11—H11B	0.9600
C2—H2B	0.9700	C11—H11C	0.9600
C3—C4	1.523 (3)	C12—C13	1.468 (3)
C3—H3A	0.9700	C12—C14	1.489 (3)
C3—H3B	0.9700	C14—C19	1.392 (3)
C4—C5	1.523 (4)	C14—C15	1.394 (3)
C4—H4A	0.9700	C15—C16	1.387 (3)
C4—H4B	0.9700	C16—C17	1.381 (3)
C5—C6	1.533 (3)	C16—H16	0.9300
C5—H5A	0.9700	C17—C18	1.382 (3)
C5—H5B	0.9700	C18—C19	1.387 (3)
C6—H6A	0.9700	C18—H18	0.9300
C6—H6B	0.9700	C19—H19	0.9300

C13—O1—C1	109.23 (17)	C9—C8—H8B	110.4
C7—O3—C8	118.25 (16)	H8A—C8—H8B	108.6
O1—C1—C7	103.00 (15)	C8—C9—C10	113.7 (2)
O1—C1—C2	108.6 (2)	C8—C9—H9A	108.8
C7—C1—C2	111.05 (17)	C10—C9—H9A	108.8
O1—C1—C6	109.07 (16)	C8—C9—H9B	108.8
C7—C1—C6	113.8 (2)	C10—C9—H9B	108.8
C2—C1—C6	110.88 (17)	H9A—C9—H9B	107.7
C1—C2—C3	112.31 (18)	C9—C10—C11	111.7 (2)
C1—C2—H2A	109.1	C9—C10—H10A	109.3
C3—C2—H2A	109.1	C11—C10—H10A	109.3
C1—C2—H2B	109.1	C9—C10—H10B	109.3
C3—C2—H2B	109.1	C11—C10—H10B	109.3
H2A—C2—H2B	107.9	H10A—C10—H10B	107.9
C4—C3—C2	110.3 (2)	C10—C11—H11A	109.5
C4—C3—H3A	109.6	C10—C11—H11B	109.5
C2—C3—H3A	109.6	H11A—C11—H11B	109.5
C4—C3—H3B	109.6	C10—C11—H11C	109.5
C2—C3—H3B	109.6	H11A—C11—H11C	109.5
H3A—C3—H3B	108.1	H11B—C11—H11C	109.5
C3—C4—C5	111.63 (18)	C7—C12—C13	106.35 (19)
C3—C4—H4A	109.3	C7—C12—C14	133.3 (2)
C5—C4—H4A	109.3	C13—C12—C14	120.29 (18)
C3—C4—H4B	109.3	O2—C13—O1	121.0 (2)
C5—C4—H4B	109.3	O2—C13—C12	129.3 (2)
H4A—C4—H4B	108.0	O1—C13—C12	109.68 (18)
C4—C5—C6	112.01 (19)	C19—C14—C15	117.2 (2)
C4—C5—H5A	109.2	C19—C14—C12	122.2 (2)
C6—C5—H5A	109.2	C15—C14—C12	120.5 (2)
C4—C5—H5B	109.2	C16—C15—C14	122.5 (2)
C6—C5—H5B	109.2	C16—C15—Cl1	118.24 (18)
H5A—C5—H5B	107.9	C14—C15—Cl1	119.23 (17)
C5—C6—C1	111.5 (2)	C17—C16—C15	117.8 (2)
C5—C6—H6A	109.3	C17—C16—H16	121.1
C1—C6—H6A	109.3	C15—C16—H16	121.1
C5—C6—H6B	109.3	C16—C17—C18	122.1 (2)
C1—C6—H6B	109.3	C16—C17—Cl2	118.49 (19)
H6A—C6—H6B	108.0	C18—C17—Cl2	119.44 (19)
O3—C7—C12	133.7 (2)	C17—C18—C19	118.5 (2)
O3—C7—C1	114.69 (17)	C17—C18—H18	120.8
C12—C7—C1	111.49 (19)	C19—C18—H18	120.8
O3—C8—C9	106.70 (16)	C18—C19—C14	121.9 (2)
O3—C8—H8A	110.4	C18—C19—H19	119.1
C9—C8—H8A	110.4	C14—C19—H19	119.1
O3—C8—H8B	110.4

C13—O1—C1—C7	−5.1 (2)	O3—C7—C12—C14	0.6 (5)
C13—O1—C1—C2	112.8 (2)	C1—C7—C12—C14	176.3 (2)
C13—O1—C1—C6	−126.3 (2)	C1—O1—C13—O2	−174.7 (2)
O1—C1—C2—C3	64.3 (2)	C1—O1—C13—C12	4.5 (3)
C7—C1—C2—C3	176.88 (19)	C7—C12—C13—O2	177.3 (3)
C6—C1—C2—C3	−55.5 (3)	C14—C12—C13—O2	−0.8 (4)
C1—C2—C3—C4	56.3 (2)	C7—C12—C13—O1	−1.9 (3)
C2—C3—C4—C5	−55.4 (3)	C14—C12—C13—O1	−179.97 (19)
C3—C4—C5—C6	54.8 (3)	C7—C12—C14—C19	84.9 (3)
C4—C5—C6—C1	−53.5 (3)	C13—C12—C14—C19	−97.6 (3)
O1—C1—C6—C5	−66.1 (2)	C7—C12—C14—C15	−99.4 (3)
C7—C1—C6—C5	179.54 (18)	C13—C12—C14—C15	78.1 (3)
C2—C1—C6—C5	53.5 (2)	C19—C14—C15—C16	2.1 (3)
C8—O3—C7—C12	10.9 (4)	C12—C14—C15—C16	−173.8 (2)
C8—O3—C7—C1	−164.6 (2)	C19—C14—C15—Cl1	−178.01 (16)
O1—C1—C7—O3	−179.45 (18)	C12—C14—C15—Cl1	6.0 (3)
C2—C1—C7—O3	64.5 (3)	C14—C15—C16—C17	0.1 (3)
C6—C1—C7—O3	−61.5 (2)	Cl1—C15—C16—C17	−179.75 (17)
O1—C1—C7—C12	4.0 (2)	C15—C16—C17—C18	−2.6 (4)
C2—C1—C7—C12	−112.1 (2)	C15—C16—C17—Cl2	176.63 (17)
C6—C1—C7—C12	122.0 (2)	C16—C17—C18—C19	2.8 (4)
C7—O3—C8—C9	166.18 (19)	Cl2—C17—C18—C19	−176.49 (18)
O3—C8—C9—C10	−58.8 (2)	C17—C18—C19—C14	−0.4 (4)
C8—C9—C10—C11	−176.20 (18)	C15—C14—C19—C18	−2.0 (3)
O3—C7—C12—C13	−177.1 (2)	C12—C14—C19—C18	173.9 (2)
C1—C7—C12—C13	−1.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O2ⁱ	0.97	2.54	3.316 (3)	137
C18—H18···O1ⁱⁱ	0.93	2.49	3.370 (3)	159

Symmetry codes: (i) x+1/2, y, −z+1/2; (ii) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₂Cl₂O₃
M_r	369.27
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	113
a, b, c (Å)	15.177 (3), 13.735 (3), 17.497 (4)
V (Å³)	3647.4 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.18 × 0.14 × 0.10

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.936, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	23387, 3217, 2536
R_int	0.090
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.131, 1.08
No. of reflections	3217
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.35

Computer programs: CrystalClear (Rigaku, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O2ⁱ	0.97	2.54	3.316 (3)	136.7
C18—H18···O1ⁱⁱ	0.93	2.49	3.370 (3)	158.5

Symmetry codes: (i) x+1/2, y, −z+1/2; (ii) −x, y−1/2, −z+1/2.

References

Raeppel, S., Raeppl, F. & Suffert, J. (1998). Synlett, pp. 794-796. CrossRef Google Scholar
Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sarcevic, N., Zsindely, J. & Schmid, H. (1973). Helv. Chim. Acta, 56, 1457–1476. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thomas, B., Jordi, B. B., Reiner, F. & Ralf, N. (2003). Chimia, 57, 697–701. Google Scholar

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Volume 65| Part 2| February 2009| Page o302

doi:10.1107/S1600536809000579

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