1-[(2-Methyl­piperidin-1-yl)(phen­yl)meth­yl]naphthalen-2-ol

Huang, Y.

doi:10.1107/S1600536812038652

organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o2943

https://doi.org/10.1107/S1600536812038652

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1-[(2-Methylpiperidin-1-yl)(phenyl)methyl]naphthalen-2-ol

Yao Huang ^a ^*

^aSchool of Chemical Engineering, Yunnan Radio and TV University, Kunming 650023, People's Republic of China
^*Correspondence e-mail: huangyao308sys@yahoo.com.cn

(Received 11 June 2012; accepted 9 September 2012; online 15 September 2012)

In the title compound, C₂₃H₂₅NO, an intramolecular O—H⋯N hydrogen bond defines the molecular conformation; the naphthol mean plane and the benzene ring form a dihedral angle of 75.8 (2)°. The piperidine ring adopts a chair conformation. The crystal packing exhibits no short intermolecular contacts.

Related literature

For the crystal structures of related compounds, see: Wang & Zhao (2009 ); Lu et al. (2002 ). For background to Betti-type reactions, see: Pu & Yu (2001 ).

Experimental

Crystal data

C₂₃H₂₅NO
M_r = 331.44
Orthorhombic, P n a 2₁
a = 10.249 (2) Å
b = 13.182 (3) Å
c = 13.435 (3) Å
V = 1815.1 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.34 × 0.32 × 0.26 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.097, T_max = 0.099
18098 measured reflections
2170 independent reflections
1718 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.162
S = 1.13
2170 reflections
228 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.82	1.85	2.581 (4)	148

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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 I, global. DOI: https://doi.org/10.1107/S1600536812038652/cv5314sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038652/cv5314Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812038652/cv5314Isup3.cml

checkCIF report

Comment top

The so-called Betti base derivatives, which can be synthesized by many ways (Pu & Yu, 2001), are important for coordination chemistry. Herein we present the title compound, (I), obtained by solvent free, one-pot, three-component domino reaction of naphthalen-2-ol, benzaldehyde and 2-methylpiperidine.

In (I) (Fig. 1), the bond lengths and angles are within the expected ranges corresponding to those observed in the related compounds (Wang & Zhao 2009; Lu et al. 2002). The dihedral angle between the naphthalene ring system and the benzene ring is 75.8 (2)°. The piperidine ring adopts a chair conformation, An intramolecular O—H···N hydrogen bond (Table 1) stabilize the molecular conformation. The crystal packing exhibits no short intermolecular contacts.

Related literature top

For the crystal structures of related compounds, see: Wang & Zhao (2009); Lu et al. (2002). For background to Betti-type reactions, see: Pu & Yu (2001).

Experimental top

A dry 50 ml flask was charged with benzaldehyde (10 mmol), naphthalen-2-ol (10 mmol) and 2-methylpiperidine (10 mmol). The mixture was stirred at 100°C for 5 h and then ethanol (15 ml) was added. After refluxing for 30 minutes, the mixed solution was filtered and crystals of the title compound suitable for X-ray analysis was obtained by slow evaporation.

Structure description top

For the crystal structures of related compounds, see: Wang & Zhao (2009); Lu et al. (2002). For background to Betti-type reactions, see: Pu & Yu (2001).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 the title compound with displacement ellipsoids drawn at the 30% probability level. Intramolecular hydrogen bond is shown as dashed line.

1-[(2-Methylpiperidin-1-yl)(phenyl)methyl]naphthalen-2-ol top

Crystal data top

C₂₃H₂₅NO	F(000) = 712
M_r = 331.44	D_x = 1.213 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2170 reflections
a = 10.249 (2) Å	θ = 2.2–27.5°
b = 13.182 (3) Å	µ = 0.07 mm⁻¹
c = 13.435 (3) Å	T = 293 K
V = 1815.1 (6) Å³	Block, pale yellow
Z = 4	0.34 × 0.32 × 0.26 mm

Data collection top

Rigaku SCXmini diffractometer	2170 independent reflections
Radiation source: fine-focus sealed tube	1718 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 2.2°
CCD_Profile_fitting scans	h = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −17→17
T_min = 0.097, T_max = 0.099	l = −17→17
18098 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.162	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0945P)² + 0.0807P] where P = (F_o² + 2F_c²)/3
2170 reflections	(Δ/σ)_max < 0.001
228 parameters	Δρ_max = 0.32 e Å⁻³
1 restraint	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₃H₂₅NO	V = 1815.1 (6) Å³
M_r = 331.44	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 10.249 (2) Å	µ = 0.07 mm⁻¹
b = 13.182 (3) Å	T = 293 K
c = 13.435 (3) Å	0.34 × 0.32 × 0.26 mm

Data collection top

Rigaku SCXmini diffractometer	2170 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1718 reflections with I > 2σ(I)
T_min = 0.097, T_max = 0.099	R_int = 0.058
18098 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	1 restraint
wR(F²) = 0.162	H-atom parameters constrained
S = 1.13	Δρ_max = 0.32 e Å⁻³
2170 reflections	Δρ_min = −0.20 e Å⁻³
228 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	0.6335 (3)	0.5998 (2)	0.4126 (3)	0.0416 (7)
H1	0.5935	0.6338	0.4698	0.050*
C2	0.7644 (3)	0.5578 (2)	0.4460 (2)	0.0385 (7)
C3	0.8185 (3)	0.4734 (2)	0.4004 (2)	0.0419 (7)
C4	0.9413 (4)	0.4362 (3)	0.4301 (3)	0.0506 (9)
H4	0.9770	0.3805	0.3975	0.061*
C5	1.0082 (4)	0.4805 (3)	0.5052 (3)	0.0530 (9)
H5	1.0886	0.4541	0.5243	0.064*
C6	0.9578 (3)	0.5657 (3)	0.5550 (2)	0.0432 (8)
C7	0.8359 (3)	0.6068 (2)	0.5242 (2)	0.0377 (7)
C8	0.7907 (4)	0.6945 (3)	0.5741 (3)	0.0471 (8)
H8	0.7121	0.7239	0.5549	0.057*
C9	0.8611 (4)	0.7370 (3)	0.6504 (3)	0.0570 (10)
H9	0.8293	0.7945	0.6824	0.068*
C10	0.9793 (4)	0.6952 (3)	0.6805 (3)	0.0597 (10)
H10	1.0260	0.7246	0.7324	0.072*
C11	1.0262 (4)	0.6118 (3)	0.6343 (3)	0.0564 (10)
H11	1.1051	0.5842	0.6552	0.068*
C12	0.6500 (3)	0.6787 (2)	0.3296 (3)	0.0440 (8)
C13	0.5835 (4)	0.7694 (3)	0.3331 (4)	0.0680 (12)
H13	0.5275	0.7824	0.3860	0.082*
C14	0.5983 (5)	0.8419 (3)	0.2589 (5)	0.0799 (14)
H14	0.5513	0.9022	0.2620	0.096*
C15	0.6808 (5)	0.8253 (3)	0.1821 (4)	0.0728 (13)
H15	0.6912	0.8744	0.1330	0.087*
C16	0.7491 (5)	0.7361 (4)	0.1767 (4)	0.0680 (12)
H16	0.8050	0.7242	0.1235	0.082*
C17	0.7347 (4)	0.6639 (3)	0.2505 (3)	0.0535 (9)
H17	0.7828	0.6042	0.2470	0.064*
C18	0.4314 (4)	0.5414 (3)	0.3252 (4)	0.0650 (12)
H18A	0.4571	0.5831	0.2691	0.078*
H18B	0.3718	0.5803	0.3662	0.078*
C19	0.3633 (5)	0.4449 (3)	0.2877 (5)	0.0781 (15)
H19A	0.2838	0.4635	0.2531	0.094*
H19B	0.4199	0.4105	0.2407	0.094*
C20	0.3305 (5)	0.3737 (4)	0.3718 (4)	0.0833 (16)
H20A	0.2629	0.4035	0.4130	0.100*
H20B	0.2974	0.3105	0.3449	0.100*
C21	0.4491 (5)	0.3531 (4)	0.4338 (4)	0.0765 (14)
H21A	0.5118	0.3152	0.3945	0.092*
H21B	0.4246	0.3115	0.4904	0.092*
C22	0.5127 (5)	0.4498 (4)	0.4711 (3)	0.0703 (13)
H22	0.5941	0.4312	0.5047	0.084*
C23	0.4262 (8)	0.5059 (6)	0.5467 (5)	0.120 (3)
H23A	0.3499	0.5315	0.5137	0.180*
H23B	0.4741	0.5613	0.5752	0.180*
H23C	0.4005	0.4598	0.5985	0.180*
N1	0.5467 (3)	0.5133 (2)	0.3834 (2)	0.0442 (7)
O1	0.7570 (3)	0.4224 (2)	0.3269 (2)	0.0563 (7)
H1A	0.6793	0.4373	0.3270	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0343 (16)	0.0435 (17)	0.0469 (18)	−0.0004 (12)	0.0041 (13)	−0.0160 (14)
C2	0.0350 (16)	0.0405 (16)	0.0401 (17)	−0.0022 (12)	0.0054 (13)	−0.0026 (13)
C3	0.0427 (17)	0.0414 (16)	0.0415 (18)	0.0026 (13)	0.0056 (14)	−0.0064 (14)
C4	0.049 (2)	0.0487 (19)	0.054 (2)	0.0105 (15)	0.0051 (16)	−0.0041 (16)
C5	0.0392 (18)	0.061 (2)	0.059 (2)	0.0085 (16)	0.0010 (16)	0.0044 (18)
C6	0.0407 (17)	0.0453 (18)	0.0435 (18)	−0.0080 (13)	0.0016 (14)	0.0085 (13)
C7	0.0391 (16)	0.0371 (14)	0.0368 (15)	−0.0072 (12)	0.0023 (13)	0.0022 (12)
C8	0.048 (2)	0.0457 (19)	0.0472 (19)	−0.0036 (14)	0.0029 (16)	−0.0080 (15)
C9	0.072 (3)	0.0490 (19)	0.050 (2)	−0.0160 (18)	0.0031 (19)	−0.0113 (17)
C10	0.073 (3)	0.059 (2)	0.047 (2)	−0.0227 (19)	−0.019 (2)	−0.0014 (18)
C11	0.054 (2)	0.063 (2)	0.052 (2)	−0.0093 (18)	−0.0151 (18)	0.0111 (18)
C12	0.0361 (17)	0.0417 (16)	0.0543 (19)	−0.0002 (12)	−0.0070 (15)	−0.0090 (15)
C13	0.053 (2)	0.055 (2)	0.095 (3)	0.0091 (18)	0.003 (2)	−0.003 (2)
C14	0.067 (3)	0.049 (2)	0.123 (4)	0.009 (2)	−0.012 (3)	0.015 (3)
C15	0.071 (3)	0.063 (3)	0.085 (3)	−0.009 (2)	−0.029 (3)	0.020 (2)
C16	0.079 (3)	0.072 (3)	0.053 (2)	−0.002 (2)	−0.002 (2)	0.008 (2)
C17	0.062 (2)	0.049 (2)	0.049 (2)	0.0051 (16)	−0.0020 (17)	−0.0045 (16)
C18	0.040 (2)	0.056 (2)	0.099 (3)	0.0055 (16)	−0.021 (2)	−0.028 (2)
C19	0.054 (3)	0.066 (3)	0.114 (4)	−0.004 (2)	−0.023 (3)	−0.030 (3)
C20	0.060 (3)	0.077 (3)	0.114 (4)	−0.027 (2)	0.029 (3)	−0.038 (3)
C21	0.082 (3)	0.071 (3)	0.076 (3)	−0.031 (2)	0.021 (3)	−0.013 (2)
C22	0.080 (3)	0.073 (3)	0.057 (2)	−0.034 (2)	0.014 (2)	−0.007 (2)
C23	0.135 (6)	0.143 (6)	0.082 (4)	−0.052 (5)	0.034 (4)	−0.037 (4)
N1	0.0385 (14)	0.0450 (15)	0.0491 (16)	−0.0056 (11)	0.0005 (12)	−0.0121 (12)
O1	0.0545 (16)	0.0564 (15)	0.0581 (16)	0.0022 (11)	−0.0002 (13)	−0.0246 (13)

Geometric parameters (Å, º) top

C1—N1	1.498 (4)	C14—H14	0.9300
C1—C2	1.519 (5)	C15—C16	1.370 (7)
C1—C12	1.534 (5)	C15—H15	0.9300
C1—H1	0.9800	C16—C17	1.382 (6)
C2—C3	1.387 (4)	C16—H16	0.9300
C2—C7	1.434 (5)	C17—H17	0.9300
C3—O1	1.350 (4)	C18—N1	1.464 (5)
C3—C4	1.408 (5)	C18—C19	1.535 (5)
C4—C5	1.353 (6)	C18—H18A	0.9700
C4—H4	0.9300	C18—H18B	0.9700
C5—C6	1.406 (5)	C19—C20	1.506 (8)
C5—H5	0.9300	C19—H19A	0.9700
C6—C11	1.414 (5)	C19—H19B	0.9700
C6—C7	1.422 (5)	C20—C21	1.499 (8)
C7—C8	1.415 (5)	C20—H20A	0.9700
C8—C9	1.373 (5)	C20—H20B	0.9700
C8—H8	0.9300	C21—C22	1.517 (6)
C9—C10	1.392 (6)	C21—H21A	0.9700
C9—H9	0.9300	C21—H21B	0.9700
C10—C11	1.350 (6)	C22—N1	1.486 (5)
C10—H10	0.9300	C22—C23	1.538 (8)
C11—H11	0.9300	C22—H22	0.9800
C12—C13	1.378 (5)	C23—H23A	0.9600
C12—C17	1.387 (5)	C23—H23B	0.9600
C13—C14	1.389 (8)	C23—H23C	0.9600
C13—H13	0.9300	O1—H1A	0.8200
C14—C15	1.351 (8)

N1—C1—C2	109.0 (3)	C16—C15—H15	120.0
N1—C1—C12	113.0 (3)	C15—C16—C17	119.9 (5)
C2—C1—C12	111.4 (3)	C15—C16—H16	120.0
N1—C1—H1	107.7	C17—C16—H16	120.0
C2—C1—H1	107.7	C16—C17—C12	121.3 (4)
C12—C1—H1	107.7	C16—C17—H17	119.3
C3—C2—C7	118.7 (3)	C12—C17—H17	119.3
C3—C2—C1	120.9 (3)	N1—C18—C19	109.4 (3)
C7—C2—C1	120.3 (3)	N1—C18—H18A	109.8
O1—C3—C2	122.4 (3)	C19—C18—H18A	109.8
O1—C3—C4	116.8 (3)	N1—C18—H18B	109.8
C2—C3—C4	120.8 (3)	C19—C18—H18B	109.8
C5—C4—C3	121.0 (3)	H18A—C18—H18B	108.2
C5—C4—H4	119.5	C20—C19—C18	111.8 (4)
C3—C4—H4	119.5	C20—C19—H19A	109.2
C4—C5—C6	120.9 (3)	C18—C19—H19A	109.2
C4—C5—H5	119.6	C20—C19—H19B	109.2
C6—C5—H5	119.6	C18—C19—H19B	109.2
C5—C6—C11	121.3 (3)	H19A—C19—H19B	107.9
C5—C6—C7	119.3 (3)	C21—C20—C19	110.4 (4)
C11—C6—C7	119.4 (3)	C21—C20—H20A	109.6
C8—C7—C6	117.5 (3)	C19—C20—H20A	109.6
C8—C7—C2	123.1 (3)	C21—C20—H20B	109.6
C6—C7—C2	119.4 (3)	C19—C20—H20B	109.6
C9—C8—C7	121.0 (4)	H20A—C20—H20B	108.1
C9—C8—H8	119.5	C20—C21—C22	112.3 (4)
C7—C8—H8	119.5	C20—C21—H21A	109.1
C8—C9—C10	120.9 (4)	C22—C21—H21A	109.1
C8—C9—H9	119.6	C20—C21—H21B	109.1
C10—C9—H9	119.6	C22—C21—H21B	109.1
C11—C10—C9	119.9 (4)	H21A—C21—H21B	107.9
C11—C10—H10	120.0	N1—C22—C21	108.2 (3)
C9—C10—H10	120.0	N1—C22—C23	112.8 (5)
C10—C11—C6	121.3 (4)	C21—C22—C23	112.0 (4)
C10—C11—H11	119.3	N1—C22—H22	107.9
C6—C11—H11	119.3	C21—C22—H22	107.9
C13—C12—C17	117.2 (4)	C23—C22—H22	107.9
C13—C12—C1	120.7 (4)	C22—C23—H23A	109.5
C17—C12—C1	122.1 (3)	C22—C23—H23B	109.5
C12—C13—C14	121.3 (5)	H23A—C23—H23B	109.5
C12—C13—H13	119.4	C22—C23—H23C	109.5
C14—C13—H13	119.4	H23A—C23—H23C	109.5
C15—C14—C13	120.3 (4)	H23B—C23—H23C	109.5
C15—C14—H14	119.8	C18—N1—C22	112.1 (3)
C13—C14—H14	119.8	C18—N1—C1	115.3 (3)
C14—C15—C16	119.9 (4)	C22—N1—C1	111.1 (3)
C14—C15—H15	120.0	C3—O1—H1A	109.5

N1—C1—C2—C3	36.0 (4)	N1—C1—C12—C13	102.8 (4)
C12—C1—C2—C3	−89.4 (3)	C2—C1—C12—C13	−134.1 (4)
N1—C1—C2—C7	−145.5 (3)	N1—C1—C12—C17	−79.4 (4)
C12—C1—C2—C7	89.1 (3)	C2—C1—C12—C17	43.7 (4)
C7—C2—C3—O1	179.4 (3)	C17—C12—C13—C14	1.6 (6)
C1—C2—C3—O1	−2.1 (5)	C1—C12—C13—C14	179.4 (4)
C7—C2—C3—C4	0.0 (5)	C12—C13—C14—C15	−1.1 (8)
C1—C2—C3—C4	178.5 (3)	C13—C14—C15—C16	0.7 (7)
O1—C3—C4—C5	−177.9 (4)	C14—C15—C16—C17	−0.8 (7)
C2—C3—C4—C5	1.5 (5)	C15—C16—C17—C12	1.4 (6)
C3—C4—C5—C6	−0.9 (6)	C13—C12—C17—C16	−1.7 (6)
C4—C5—C6—C11	179.3 (4)	C1—C12—C17—C16	−179.5 (4)
C4—C5—C6—C7	−1.2 (5)	N1—C18—C19—C20	55.1 (5)
C5—C6—C7—C8	−178.0 (3)	C18—C19—C20—C21	−52.4 (5)
C11—C6—C7—C8	1.5 (5)	C19—C20—C21—C22	54.4 (5)
C5—C6—C7—C2	2.6 (4)	C20—C21—C22—N1	−57.5 (5)
C11—C6—C7—C2	−177.8 (3)	C20—C21—C22—C23	67.4 (6)
C3—C2—C7—C8	178.7 (3)	C19—C18—N1—C22	−59.9 (5)
C1—C2—C7—C8	0.1 (5)	C19—C18—N1—C1	171.6 (4)
C3—C2—C7—C6	−2.0 (4)	C21—C22—N1—C18	60.9 (5)
C1—C2—C7—C6	179.5 (3)	C23—C22—N1—C18	−63.6 (5)
C6—C7—C8—C9	−1.1 (5)	C21—C22—N1—C1	−168.5 (4)
C2—C7—C8—C9	178.2 (3)	C23—C22—N1—C1	67.0 (5)
C7—C8—C9—C10	0.3 (6)	C2—C1—N1—C18	−164.4 (3)
C8—C9—C10—C11	0.1 (6)	C12—C1—N1—C18	−40.0 (4)
C9—C10—C11—C6	0.3 (6)	C2—C1—N1—C22	66.6 (4)
C5—C6—C11—C10	178.4 (4)	C12—C1—N1—C22	−168.9 (3)
C7—C6—C11—C10	−1.1 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.85	2.581 (4)	148

Experimental details

Crystal data
Chemical formula	C₂₃H₂₅NO
M_r	331.44
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	10.249 (2), 13.182 (3), 13.435 (3)
V (Å³)	1815.1 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.34 × 0.32 × 0.26

Data collection
Diffractometer	Rigaku SCXmini
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.097, 0.099
No. of measured, independent and observed [I > 2σ(I)] reflections	18098, 2170, 1718
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.162, 1.13
No. of reflections	2170
No. of parameters	228
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.20

Computer programs: CrystalClear (Rigaku, 2005), 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
O1—H1A···N1	0.82	1.85	2.581 (4)	147.5

Acknowledgements

This work was supported by the Yunnan Provincal Science and Technology Department Applied Basic Research Program (grant No. 2011FZ198) and the Yunnan Province Department of Education Scientific Research Fund (grant No. 2011Z009).

References

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