(S)-5-Hexyl-1-[(S)-2-hydr­oxy-1-phenyl­ethyl]-4-meth­oxy-1H-pyrrol-2(5H)-one

Zheng, J.-F.; Jiang, L.-J.; Guo, J.-N.

doi:10.1107/S1600536809014160

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1094

doi:10.1107/S1600536809014160

Open

access

(S)-5-Hexyl-1-[(S)-2-hydroxy-1-phenylethyl]-4-methoxy-1H-pyrrol-2(5H)-one

Jian-Feng Zheng,^a ^* Li-Jiao Jiang ^a and Jian-Nan Guo ^a

^aDepartment of Chemistry and the Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, People's Republic of China
^*Correspondence e-mail: zjf485@xmu.edu.cn

(Received 30 March 2009; accepted 16 April 2009; online 22 April 2009)

The title compound, C₁₉H₂₇NO₃, was obtained by the reaction of (3S,7aR)-7a-hexyl-7-methoxy-3-phenyl-2,3-dihydropyrrolo[2,1-b]oxazol-5(7aH)-one and triethylsilane using titanium(IV) chloride as catalyst. In the molecule, the phenyl and dihydropyrrolone rings form a dihedral angle of 83.8 (1)°. O—H⋯O hydrogen-bonding interactions lead to the formation of a chain parallel to the a axis.

Related literature

For the bioactivity of methyl tetramates, see: Royles (1995 ). For the synthesis, see: Jiang et al. (2009 ).

Experimental

Crystal data

C₁₉H₂₇NO₃
M_r = 317.42
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.6739 (17) Å
b = 10.0995 (18) Å
c = 17.929 (3) Å
V = 1751.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 173 K
0.56 × 0.32 × 0.23 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.956, T_max = 0.982
12545 measured reflections
1773 independent reflections
1732 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.079
S = 1.13
1773 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7C⋯O2ⁱ	0.84	1.93	2.7475 (18)	163
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809014160/bt2921sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809014160/bt2921Isup2.hkl

checkCIF report

Comment top

Methyl tetramates bearing C-5 methyl substituents are key frameworks found in a number of bioactive natural products, such as dysideapyrrolidone and dolastatin (Royles, 1995). The title compound, (1), is one of the methyl tetramates which were synthesized when we researched the flexible method for the preparation of methyl (S)-5-alkyltetramate derivatives.

The title compound, (1), was obtained by the reaction of (3S,7aR)-7a-hexyl-7-methoxy-3-phenyl-2,3- dihydropyrrolo[2,1-b]oxazol-5(7aH)-one and triethylsilane using titanium (IV) chloride as catalyst. The absolute configuration (S) of the stereocentre C6 remains unchanged during the synthetic procedure. An X-ray crystal structure determination of the molecular structure of compound (1) was carried out to determine its conformation.

The phenyl and dihydropyrrolone rings form a dihedral angle of 83.8 (1)°. O—H···O hydrogen-bonding interactions lead to the formation of a chain parallel to the a axis.

Related literature top

For related literature, see: Royles (1995); Jiang et al. (2009).

Experimental top

The title compound was prepared by a method based on one described by Jiang et al. (2009). To a cooled (-78 °C) solution of (3S,7aR)-7a-hexyl-7-methoxy-3-phenyl-2,3-δihydropyrrolo[2,1-b]oxazol-5(7aH)-one (0.230 mmol) in dry dichloromethane (6 ml) was added dropwise a solution of TiCl₄ (0.245 mmol), followed by Et₃SiH (2.3 mmol) under nitrogen atmosphere. After being stirred at -78 °C for 2 h, the mixture was allowed to react at room temperature and stirred until the completion of the reaction. The mixture was quenched with saturated NaHCO₃ solution. The organic layer was separated and the aqueous phase was extracted with CH₂Cl₂ (3 × 5 ml). The combined organic layers were washed with brine, dried over Na₂SO₄, and concentrated under reduced pressure. The residue was purified by flash chromatography to give (S)-5-hexyl-1-((S)- 2-hydroxy-1-phenylethyl)-4-methoxy-1H-pyrrol-2(5H)-one as colorless crystals. Single crystals were obtained by slow evaporation of a petroleum ether/ethyl acetate solution.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with the atom-labeling scheme, showing 50% probability displacement ellipsoids. H atoms are drawn as spheres of arbitrary radius.

(S)-5-Hexyl-1-[(S)-2-hydroxy-1-phenylethyl]-4-methoxy- 1H-pyrrol-2(5H)-one top

Crystal data top

C₁₉H₂₇NO₃	F(000) = 688
M_r = 317.42	D_x = 1.204 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9516 reflections
a = 9.6739 (17) Å	θ = 4.5–56.6°
b = 10.0995 (18) Å	µ = 0.08 mm⁻¹
c = 17.929 (3) Å	T = 173 K
V = 1751.7 (5) Å³	Needle, colorless
Z = 4	0.56 × 0.32 × 0.23 mm

Data collection top

Bruker APEX CCD diffractometer	1773 independent reflections
Radiation source: fine-focus sealed tube	1732 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
T_min = 0.956, T_max = 0.982	k = −12→12
12545 measured reflections	l = −21→20

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0483P)² + 0.1818P] where P = (F_o² + 2F_c²)/3
1773 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₉H₂₇NO₃	V = 1751.7 (5) Å³
M_r = 317.42	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.6739 (17) Å	µ = 0.08 mm⁻¹
b = 10.0995 (18) Å	T = 173 K
c = 17.929 (3) Å	0.56 × 0.32 × 0.23 mm

Data collection top

Bruker APEX CCD diffractometer	1773 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1732 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.982	R_int = 0.023
12545 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.079	H-atom parameters constrained
S = 1.13	Δρ_max = 0.13 e Å⁻³
1773 reflections	Δρ_min = −0.13 e Å⁻³
208 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
N1	0.23084 (14)	0.27270 (13)	0.08925 (7)	0.0264 (3)
O2	0.01267 (12)	0.18490 (12)	0.08019 (6)	0.0339 (3)
C2	0.09444 (17)	0.26555 (17)	0.10656 (9)	0.0275 (4)
C3	0.06570 (18)	0.36770 (17)	0.16165 (9)	0.0314 (4)
H3A	−0.0223	0.3883	0.1821	0.038*
O4	0.21692 (13)	0.52314 (12)	0.22535 (7)	0.0381 (3)
C4	0.18362 (19)	0.42683 (16)	0.17823 (9)	0.0300 (4)
C5	0.30022 (18)	0.37368 (17)	0.13261 (9)	0.0294 (4)
H5A	0.3699	0.3313	0.1662	0.035*
C6	0.31243 (16)	0.17097 (16)	0.05156 (9)	0.0271 (4)
H6A	0.4059	0.2102	0.0426	0.032*
O7	0.23907 (13)	0.24369 (13)	−0.07171 (6)	0.0393 (3)
H7C	0.3167	0.2780	−0.0799	0.059*
C7	0.25486 (19)	0.13400 (18)	−0.02451 (8)	0.0324 (4)
H7A	0.3177	0.0694	−0.0485	0.039*
H7B	0.1639	0.0906	−0.0179	0.039*
C8	0.33410 (18)	0.05271 (17)	0.10152 (9)	0.0293 (4)
C9	0.2319 (2)	−0.04012 (17)	0.11356 (10)	0.0367 (4)
H9A	0.1459	−0.0318	0.0884	0.044*
C10	0.2528 (2)	−0.14481 (19)	0.16160 (11)	0.0441 (5)
H10A	0.1815	−0.2081	0.1692	0.053*
C11	0.3763 (2)	−0.1579 (2)	0.19852 (12)	0.0483 (5)
H11A	0.3907	−0.2297	0.2318	0.058*
C12	0.4785 (2)	−0.0666 (2)	0.18692 (11)	0.0460 (5)
H12A	0.5640	−0.0751	0.2125	0.055*
C13	0.45838 (19)	0.03788 (19)	0.13829 (9)	0.0360 (4)
H13A	0.5307	0.0999	0.1301	0.043*
C14	0.37058 (18)	0.47889 (17)	0.08519 (10)	0.0329 (4)
H14A	0.4189	0.5416	0.1187	0.039*
H14B	0.4415	0.4355	0.0538	0.039*
C15	0.27425 (19)	0.55665 (18)	0.03513 (10)	0.0351 (4)
H15A	0.2164	0.4941	0.0063	0.042*
H15B	0.2120	0.6111	0.0664	0.042*
C16	0.3508 (2)	0.64551 (19)	−0.01812 (11)	0.0401 (4)
H16A	0.4100	0.7065	0.0109	0.048*
H16B	0.4121	0.5905	−0.0497	0.048*
C17	0.2578 (2)	0.7259 (2)	−0.06785 (10)	0.0421 (4)
H17A	0.2078	0.7914	−0.0368	0.050*
H17B	0.1881	0.6662	−0.0903	0.050*
C18	0.3319 (2)	0.79856 (19)	−0.12980 (11)	0.0446 (5)
H18A	0.4007	0.8594	−0.1075	0.054*
H18B	0.3828	0.7334	−0.1606	0.054*
C19	0.2366 (2)	0.8770 (2)	−0.17945 (11)	0.0494 (5)
H19A	0.2908	0.9214	−0.2183	0.074*
H19B	0.1877	0.9434	−0.1496	0.074*
H19C	0.1695	0.8173	−0.2027	0.074*
C20	0.1077 (2)	0.5705 (2)	0.27166 (10)	0.0457 (5)
H20A	0.1427	0.6411	0.3041	0.069*
H20B	0.0723	0.4977	0.3023	0.069*
H20C	0.0330	0.6054	0.2404	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0263 (7)	0.0264 (7)	0.0263 (6)	−0.0003 (6)	0.0015 (5)	−0.0016 (6)
O2	0.0273 (6)	0.0347 (6)	0.0398 (6)	−0.0034 (6)	0.0012 (5)	0.0020 (5)
C2	0.0272 (8)	0.0288 (8)	0.0264 (7)	0.0012 (7)	−0.0001 (6)	0.0078 (7)
C3	0.0313 (8)	0.0318 (8)	0.0310 (8)	0.0057 (8)	0.0072 (7)	0.0056 (7)
O4	0.0436 (7)	0.0378 (7)	0.0329 (6)	0.0052 (6)	0.0017 (6)	−0.0096 (5)
C4	0.0388 (9)	0.0287 (8)	0.0224 (7)	0.0058 (7)	0.0008 (7)	0.0018 (7)
C5	0.0290 (8)	0.0308 (8)	0.0284 (8)	0.0025 (7)	−0.0025 (7)	−0.0024 (7)
C6	0.0243 (8)	0.0289 (8)	0.0281 (8)	0.0003 (7)	0.0019 (6)	−0.0037 (7)
O7	0.0343 (6)	0.0530 (8)	0.0307 (6)	0.0012 (6)	−0.0036 (5)	0.0045 (6)
C7	0.0314 (8)	0.0381 (9)	0.0275 (8)	−0.0015 (8)	0.0000 (7)	−0.0037 (7)
C8	0.0313 (8)	0.0287 (8)	0.0278 (8)	0.0034 (7)	0.0031 (7)	−0.0057 (7)
C9	0.0338 (9)	0.0325 (9)	0.0436 (9)	0.0001 (8)	−0.0015 (8)	−0.0013 (8)
C10	0.0493 (11)	0.0299 (9)	0.0532 (11)	−0.0018 (9)	0.0058 (10)	0.0034 (8)
C11	0.0597 (13)	0.0384 (10)	0.0468 (11)	0.0123 (10)	0.0018 (10)	0.0090 (9)
C12	0.0426 (11)	0.0520 (11)	0.0433 (10)	0.0109 (10)	−0.0065 (9)	0.0057 (10)
C13	0.0341 (9)	0.0378 (9)	0.0360 (8)	0.0014 (8)	−0.0007 (7)	−0.0018 (8)
C14	0.0284 (8)	0.0334 (9)	0.0370 (9)	−0.0021 (8)	0.0019 (7)	−0.0065 (7)
C15	0.0346 (9)	0.0349 (9)	0.0358 (8)	−0.0044 (8)	0.0029 (8)	−0.0008 (7)
C16	0.0397 (10)	0.0374 (10)	0.0433 (10)	−0.0016 (8)	0.0088 (8)	0.0020 (8)
C17	0.0441 (11)	0.0431 (10)	0.0390 (9)	−0.0063 (9)	0.0020 (9)	0.0034 (8)
C18	0.0523 (11)	0.0360 (9)	0.0455 (10)	0.0029 (9)	0.0133 (9)	0.0044 (9)
C19	0.0588 (13)	0.0482 (11)	0.0413 (10)	−0.0072 (11)	−0.0008 (10)	0.0069 (9)
C20	0.0594 (12)	0.0422 (10)	0.0355 (9)	0.0112 (10)	0.0099 (9)	−0.0067 (8)

Geometric parameters (Å, º) top

N1—C2	1.357 (2)	C11—H11A	0.9500
N1—C5	1.447 (2)	C12—C13	1.383 (3)
N1—C6	1.461 (2)	C12—H12A	0.9500
O2—C2	1.230 (2)	C13—H13A	0.9500
C2—C3	1.455 (2)	C14—C15	1.513 (3)
C3—C4	1.321 (3)	C14—H14A	0.9900
C3—H3A	0.9500	C14—H14B	0.9900
O4—C4	1.328 (2)	C15—C16	1.505 (2)
O4—C20	1.426 (2)	C15—H15A	0.9900
C4—C5	1.493 (2)	C15—H15B	0.9900
C5—C14	1.522 (2)	C16—C17	1.505 (3)
C5—H5A	1.0000	C16—H16A	0.9900
C6—C8	1.508 (2)	C16—H16B	0.9900
C6—C7	1.520 (2)	C17—C18	1.512 (3)
C6—H6A	1.0000	C17—H17A	0.9900
O7—C7	1.402 (2)	C17—H17B	0.9900
O7—H7C	0.8400	C18—C19	1.507 (3)
C7—H7A	0.9900	C18—H18A	0.9900
C7—H7B	0.9900	C18—H18B	0.9900
C8—C13	1.379 (2)	C19—H19A	0.9800
C8—C9	1.380 (2)	C19—H19B	0.9800
C9—C10	1.379 (3)	C19—H19C	0.9800
C9—H9A	0.9500	C20—H20A	0.9800
C10—C11	1.372 (3)	C20—H20B	0.9800
C10—H10A	0.9500	C20—H20C	0.9800
C11—C12	1.368 (3)

C2—N1—C5	111.43 (14)	C13—C12—H12A	119.7
C2—N1—C6	126.40 (14)	C8—C13—C12	120.46 (18)
C5—N1—C6	119.56 (13)	C8—C13—H13A	119.8
O2—C2—N1	124.93 (16)	C12—C13—H13A	119.8
O2—C2—C3	127.41 (15)	C15—C14—C5	114.73 (14)
N1—C2—C3	107.65 (15)	C15—C14—H14A	108.6
C4—C3—C2	107.94 (15)	C5—C14—H14A	108.6
C4—C3—H3A	126.0	C15—C14—H14B	108.6
C2—C3—H3A	126.0	C5—C14—H14B	108.6
C4—O4—C20	115.87 (15)	H14A—C14—H14B	107.6
C3—C4—O4	133.12 (16)	C16—C15—C14	112.50 (15)
C3—C4—C5	111.50 (14)	C16—C15—H15A	109.1
O4—C4—C5	115.37 (15)	C14—C15—H15A	109.1
N1—C5—C4	101.38 (13)	C16—C15—H15B	109.1
N1—C5—C14	113.54 (13)	C14—C15—H15B	109.1
C4—C5—C14	113.14 (14)	H15A—C15—H15B	107.8
N1—C5—H5A	109.5	C17—C16—C15	113.79 (16)
C4—C5—H5A	109.5	C17—C16—H16A	108.8
C14—C5—H5A	109.5	C15—C16—H16A	108.8
N1—C6—C8	110.93 (12)	C17—C16—H16B	108.8
N1—C6—C7	112.95 (13)	C15—C16—H16B	108.8
C8—C6—C7	112.93 (13)	H16A—C16—H16B	107.7
N1—C6—H6A	106.5	C16—C17—C18	114.42 (17)
C8—C6—H6A	106.5	C16—C17—H17A	108.7
C7—C6—H6A	106.5	C18—C17—H17A	108.7
C7—O7—H7C	109.5	C16—C17—H17B	108.7
O7—C7—C6	112.79 (13)	C18—C17—H17B	108.7
O7—C7—H7A	109.0	H17A—C17—H17B	107.6
C6—C7—H7A	109.0	C19—C18—C17	113.52 (18)
O7—C7—H7B	109.0	C19—C18—H18A	108.9
C6—C7—H7B	109.0	C17—C18—H18A	108.9
H7A—C7—H7B	107.8	C19—C18—H18B	108.9
C13—C8—C9	118.44 (16)	C17—C18—H18B	108.9
C13—C8—C6	119.42 (16)	H18A—C18—H18B	107.7
C9—C8—C6	122.11 (16)	C18—C19—H19A	109.5
C10—C9—C8	120.91 (18)	C18—C19—H19B	109.5
C10—C9—H9A	119.5	H19A—C19—H19B	109.5
C8—C9—H9A	119.5	C18—C19—H19C	109.5
C11—C10—C9	120.20 (19)	H19A—C19—H19C	109.5
C11—C10—H10A	119.9	H19B—C19—H19C	109.5
C9—C10—H10A	119.9	O4—C20—H20A	109.5
C12—C11—C10	119.41 (18)	O4—C20—H20B	109.5
C12—C11—H11A	120.3	H20A—C20—H20B	109.5
C10—C11—H11A	120.3	O4—C20—H20C	109.5
C11—C12—C13	120.57 (19)	H20A—C20—H20C	109.5
C11—C12—H12A	119.7	H20B—C20—H20C	109.5

C5—N1—C2—O2	−176.98 (14)	C5—N1—C6—C7	−142.17 (14)
C6—N1—C2—O2	−15.5 (3)	N1—C6—C7—O7	55.07 (19)
C5—N1—C2—C3	2.15 (18)	C8—C6—C7—O7	−178.04 (14)
C6—N1—C2—C3	163.58 (13)	N1—C6—C8—C13	−100.67 (18)
O2—C2—C3—C4	175.95 (16)	C7—C6—C8—C13	131.38 (16)
N1—C2—C3—C4	−3.15 (18)	N1—C6—C8—C9	77.47 (18)
C2—C3—C4—O4	−178.40 (17)	C7—C6—C8—C9	−50.5 (2)
C2—C3—C4—C5	2.92 (19)	C13—C8—C9—C10	0.5 (3)
C20—O4—C4—C3	4.1 (3)	C6—C8—C9—C10	−177.68 (16)
C20—O4—C4—C5	−177.24 (15)	C8—C9—C10—C11	0.2 (3)
C2—N1—C5—C4	−0.46 (17)	C9—C10—C11—C12	−0.3 (3)
C6—N1—C5—C4	−163.32 (13)	C10—C11—C12—C13	−0.2 (3)
C2—N1—C5—C14	−122.12 (15)	C9—C8—C13—C12	−1.0 (3)
C6—N1—C5—C14	75.02 (18)	C6—C8—C13—C12	177.17 (16)
C3—C4—C5—N1	−1.61 (18)	C11—C12—C13—C8	0.9 (3)
O4—C4—C5—N1	179.46 (13)	N1—C5—C14—C15	60.86 (19)
C3—C4—C5—C14	120.33 (16)	C4—C5—C14—C15	−53.98 (19)
O4—C4—C5—C14	−58.60 (19)	C5—C14—C15—C16	−171.94 (15)
C2—N1—C6—C8	−70.19 (19)	C14—C15—C16—C17	−179.05 (15)
C5—N1—C6—C8	89.88 (17)	C15—C16—C17—C18	−170.57 (17)
C2—N1—C6—C7	57.8 (2)	C16—C17—C18—C19	179.28 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7C···O2ⁱ	0.84	1.93	2.7475 (18)	163

Symmetry code: (i) x+1/2, −y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₇NO₃
M_r	317.42
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	173
a, b, c (Å)	9.6739 (17), 10.0995 (18), 17.929 (3)
V (Å³)	1751.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.56 × 0.32 × 0.23

Data collection
Diffractometer	Bruker APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.956, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	12545, 1773, 1732
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.079, 1.13
No. of reflections	1773
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.13

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7C···O2ⁱ	0.84	1.93	2.7475 (18)	163.3

Symmetry code: (i) x+1/2, −y+1/2, −z.

Acknowledgements

The authors thank the Xiamen University Science Foundation (grant No. XDKJCX20053013) and the Xiamen Science Foundation (grant No. 3502Z20055019) for financial support. The authors also thank Mr Zan-Bin Wei for technical assistance.

References

Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Jiang, L. J., Lan, H. Q., Zheng, J. F., Ye, J.-L. & Huang, P. Q. (2009). Synlett. pp. 297–301. Google Scholar
Royles, B. J. L. (1995). Chem. Rev. 95, 1981–2001. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar