1-[(3-Methyl­piperidin-1-yl)(phen­yl)meth­yl]-2-naphthol

Wang, W.X.; Zhao, H.

doi:10.1107/S1600536809017176

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1277

doi:10.1107/S1600536809017176

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1-[(3-Methylpiperidin-1-yl)(phenyl)methyl]-2-naphthol

Wen Xiang Wang ^a and Hong Zhao ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: zhaohong@seu.edu.cn

(Received 25 April 2009; accepted 7 May 2009; online 14 May 2009)

In the title compound, C₂₃H₂₅NO, the dihedral angle between the naphthylene ring system and the benzene ring is 78.17 (10)°. The molecular conformation is stabilized by a strong intramolecular O—H⋯N hydrogen bond.

Related literature

For the structures of related compounds, see: Szatmari & Fulop (2004 ); Zhao & Sun (2005 ); Wang & Zhao (2008 ); Wan & Zhao (2008 ).

Experimental

Crystal data

C₂₃H₂₅NO
M_r = 331.44
Monoclinic, P 2₁ /n
a = 9.2138 (13) Å
b = 10.9056 (13) Å
c = 18.635 (3) Å
β = 97.007 (10)°
V = 1858.5 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 292 K
0.30 × 0.25 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.965, T_max = 0.979
19217 measured reflections
4422 independent reflections
2302 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.155
S = 0.99
4422 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 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	1.84	2.570 (2)	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/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809017176/rz2319sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809017176/rz2319Isup2.hkl

checkCIF report

Comment top

It is well known that many compounds derived from naphthalen-2-ol have received much attention in organic chemistry (Szatmari & Fulop, 2004; Zhao & Sun, 2005). Recently, we reported the synthesis and crystal structures of 1-[(dimethylamino)(phenyl)methyl]naphthalen-2-ol (Wang & Zhao, 2008) and 1-[pyrrolidin-1-yl(p-tolyl)methyl]naphthalen-2-ol (Wan & Zhao, 2008). We now report the crystal structure of the title compound.

Bond lengths and angles in the title compound have normal values. The dihedral angle between the naphthyl and phenyl rings is 78.17 (10)°. The molecular conformation is stabilized by a strong intramolecular O—H···N hydrogen bond (Table 1). The crystal packing is mainly stabilized by van der Waals interactions.

Related literature top

For the structures of related compounds, see: Szatmari & Fulop (2004); Zhao & Sun (2005); Wang & Zhao (2008); Wan & Zhao (2008).

Experimental top

A dry 50 ml flask was charged with benzaldehyde (10 mmol), naphthalen-2-ol (10 mmol) and 3-methylpiperidine (10 mmol). The mixture was stirred at 373 K for 10 h, then ethanol (15 ml) was added. After heating under reflux for 30 min, the precipitate was filtrated off and washed 3 times with ethanol to give the title compound. Single crystals suitable for X-ray analysis were obtained by slow evaporation of a dichloromethane solution.

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/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

1-[(3-methylpiperidin-1-yl)(phenyl)methyl]-2-naphthol top

Crystal data top

C₂₃H₂₅NO	F(000) = 712
M_r = 331.44	D_x = 1.185 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2989 reflections
a = 9.2138 (13) Å	θ = 2.6–27.9°
b = 10.9056 (13) Å	µ = 0.07 mm⁻¹
c = 18.635 (3) Å	T = 292 K
β = 97.007 (10)°	Prism, pale yellow
V = 1858.5 (5) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Rigaku SCXmini diffractometer	4422 independent reflections
Radiation source: fine-focus sealed tube	2302 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.067
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.9°, θ_min = 2.9°
ω scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −14→14
T_min = 0.965, T_max = 0.979	l = −24→24
19217 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.155	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0693P)²] where P = (F_o² + 2F_c²)/3
4422 reflections	(Δ/σ)_max < 0.001
228 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₃H₂₅NO	V = 1858.5 (5) Å³
M_r = 331.44	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.2138 (13) Å	µ = 0.07 mm⁻¹
b = 10.9056 (13) Å	T = 292 K
c = 18.635 (3) Å	0.30 × 0.25 × 0.20 mm
β = 97.007 (10)°

Data collection top

Rigaku SCXmini diffractometer	4422 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2302 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.979	R_int = 0.067
19217 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.155	H-atom parameters constrained
S = 0.99	Δρ_max = 0.15 e Å⁻³
4422 reflections	Δρ_min = −0.16 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	0.67985 (19)	0.98342 (18)	0.20764 (10)	0.0429 (5)
H1	0.6443	1.0644	0.2203	0.051*
C2	0.78426 (19)	0.93769 (17)	0.27180 (10)	0.0424 (5)
C3	0.9016 (2)	0.86366 (18)	0.26209 (11)	0.0473 (5)
C4	0.9972 (2)	0.8201 (2)	0.32150 (13)	0.0588 (6)
H4	1.0778	0.7728	0.3138	0.071*
C5	0.9718 (2)	0.8470 (2)	0.38980 (13)	0.0640 (6)
H5	1.0349	0.8168	0.4285	0.077*
C6	0.8527 (2)	0.9195 (2)	0.40364 (11)	0.0560 (6)
C7	0.7590 (2)	0.96718 (17)	0.34408 (10)	0.0466 (5)
C8	0.6424 (2)	1.04328 (19)	0.36039 (12)	0.0580 (6)
H8	0.5790	1.0764	0.3227	0.070*
C9	0.6211 (3)	1.0690 (2)	0.42986 (13)	0.0739 (7)
H9	0.5445	1.1201	0.4388	0.089*
C10	0.7124 (3)	1.0197 (3)	0.48762 (14)	0.0845 (9)
H10	0.6959	1.0367	0.5349	0.101*
C11	0.8255 (3)	0.9467 (2)	0.47479 (12)	0.0724 (7)
H11	0.8863	0.9139	0.5136	0.087*
C12	0.5482 (2)	0.89924 (19)	0.19333 (10)	0.0466 (5)
C13	0.4093 (2)	0.9444 (2)	0.19799 (11)	0.0601 (6)
H13	0.3973	1.0267	0.2090	0.072*
C14	0.2885 (2)	0.8692 (3)	0.18655 (13)	0.0719 (7)
H14	0.1959	0.9008	0.1901	0.086*
C15	0.3047 (3)	0.7479 (3)	0.16990 (13)	0.0713 (7)
H15	0.2231	0.6972	0.1620	0.086*
C16	0.4413 (2)	0.7016 (2)	0.16489 (11)	0.0655 (6)
H16	0.4524	0.6193	0.1536	0.079*
C17	0.5626 (2)	0.7767 (2)	0.17657 (11)	0.0541 (5)
H17	0.6550	0.7444	0.1731	0.065*
C18	0.6619 (2)	1.0167 (2)	0.07506 (10)	0.0580 (6)
H18A	0.6042	1.0904	0.0784	0.070*
H18B	0.5954	0.9477	0.0671	0.070*
C19	0.7514 (2)	1.0277 (2)	0.01231 (11)	0.0680 (7)
H19A	0.8024	0.9511	0.0068	0.082*
H19B	0.6864	1.0421	−0.0318	0.082*
C20	0.8616 (2)	1.1307 (2)	0.02313 (11)	0.0634 (6)
H20A	0.8106	1.2087	0.0216	0.076*
H20B	0.9225	1.1298	−0.0158	0.076*
C21	0.9571 (2)	1.11783 (19)	0.09503 (11)	0.0531 (5)
H21	1.0152	1.0428	0.0935	0.064*
C22	0.8604 (2)	1.10436 (19)	0.15507 (11)	0.0509 (5)
H22A	0.9217	1.0940	0.2008	0.061*
H22B	0.8038	1.1788	0.1580	0.061*
C23	1.0612 (3)	1.2248 (2)	0.11110 (14)	0.0819 (8)
H23A	1.0064	1.2996	0.1113	0.123*
H23B	1.1262	1.2293	0.0746	0.123*
H23C	1.1171	1.2132	0.1576	0.123*
N1	0.75966 (16)	0.99877 (14)	0.14314 (8)	0.0455 (4)
O1	0.93357 (14)	0.82835 (13)	0.19587 (8)	0.0575 (4)
H1A	0.8851	0.8690	0.1646	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0391 (10)	0.0487 (11)	0.0419 (11)	0.0029 (9)	0.0094 (8)	−0.0008 (9)
C2	0.0363 (10)	0.0451 (10)	0.0454 (11)	−0.0067 (9)	0.0030 (8)	−0.0013 (9)
C3	0.0389 (11)	0.0505 (12)	0.0522 (13)	−0.0056 (9)	0.0047 (9)	−0.0016 (10)
C4	0.0405 (11)	0.0570 (13)	0.0758 (17)	−0.0008 (10)	−0.0054 (11)	0.0039 (12)
C5	0.0608 (15)	0.0662 (15)	0.0594 (16)	−0.0155 (13)	−0.0149 (11)	0.0122 (12)
C6	0.0570 (13)	0.0584 (14)	0.0507 (13)	−0.0203 (12)	−0.0008 (10)	0.0018 (11)
C7	0.0485 (12)	0.0482 (11)	0.0435 (12)	−0.0139 (10)	0.0070 (9)	−0.0010 (9)
C8	0.0602 (14)	0.0652 (14)	0.0513 (13)	−0.0089 (12)	0.0177 (10)	−0.0074 (11)
C9	0.0778 (17)	0.0849 (18)	0.0635 (17)	−0.0153 (15)	0.0265 (14)	−0.0185 (14)
C10	0.100 (2)	0.105 (2)	0.0508 (16)	−0.0353 (18)	0.0194 (15)	−0.0203 (15)
C11	0.0845 (18)	0.0852 (18)	0.0454 (14)	−0.0310 (16)	−0.0009 (12)	0.0018 (13)
C12	0.0365 (10)	0.0610 (13)	0.0423 (11)	0.0007 (10)	0.0045 (8)	0.0067 (10)
C13	0.0417 (12)	0.0763 (15)	0.0633 (14)	0.0043 (12)	0.0100 (10)	0.0097 (12)
C14	0.0362 (12)	0.109 (2)	0.0708 (16)	−0.0001 (14)	0.0087 (11)	0.0197 (15)
C15	0.0502 (14)	0.095 (2)	0.0660 (15)	−0.0220 (14)	−0.0047 (11)	0.0137 (14)
C16	0.0624 (15)	0.0728 (16)	0.0578 (14)	−0.0103 (13)	−0.0066 (11)	−0.0003 (12)
C17	0.0418 (11)	0.0633 (13)	0.0557 (13)	−0.0011 (11)	0.0001 (9)	−0.0021 (11)
C18	0.0482 (12)	0.0814 (16)	0.0437 (12)	0.0037 (11)	0.0036 (10)	0.0040 (11)
C19	0.0598 (14)	0.1003 (19)	0.0444 (13)	−0.0009 (14)	0.0082 (10)	0.0022 (12)
C20	0.0637 (14)	0.0794 (16)	0.0503 (13)	0.0048 (13)	0.0201 (11)	0.0082 (12)
C21	0.0520 (12)	0.0551 (12)	0.0551 (13)	−0.0024 (10)	0.0184 (10)	−0.0001 (10)
C22	0.0498 (12)	0.0539 (12)	0.0500 (12)	−0.0030 (10)	0.0105 (9)	−0.0017 (10)
C23	0.0856 (18)	0.0819 (17)	0.0834 (18)	−0.0242 (15)	0.0308 (14)	−0.0037 (14)
N1	0.0394 (9)	0.0572 (10)	0.0403 (9)	−0.0036 (8)	0.0065 (7)	−0.0003 (8)
O1	0.0443 (8)	0.0662 (10)	0.0620 (10)	0.0069 (7)	0.0062 (7)	−0.0071 (8)

Geometric parameters (Å, º) top

C1—N1	1.493 (2)	C14—H14	0.9300
C1—C12	1.518 (3)	C15—C16	1.370 (3)
C1—C2	1.524 (3)	C15—H15	0.9300
C1—H1	0.9800	C16—C17	1.381 (3)
C2—C3	1.379 (3)	C16—H16	0.9300
C2—C7	1.431 (3)	C17—H17	0.9300
C3—O1	1.359 (2)	C18—N1	1.477 (2)
C3—C4	1.411 (3)	C18—C19	1.516 (3)
C4—C5	1.354 (3)	C18—H18A	0.9700
C4—H4	0.9300	C18—H18B	0.9700
C5—C6	1.402 (3)	C19—C20	1.510 (3)
C5—H5	0.9300	C19—H19A	0.9700
C6—C11	1.410 (3)	C19—H19B	0.9700
C6—C7	1.419 (3)	C20—C21	1.517 (3)
C7—C8	1.419 (3)	C20—H20A	0.9700
C8—C9	1.362 (3)	C20—H20B	0.9700
C8—H8	0.9300	C21—C23	1.517 (3)
C9—C10	1.391 (4)	C21—C22	1.520 (3)
C9—H9	0.9300	C21—H21	0.9800
C10—C11	1.356 (4)	C22—N1	1.479 (2)
C10—H10	0.9300	C22—H22A	0.9700
C11—H11	0.9300	C22—H22B	0.9700
C12—C17	1.383 (3)	C23—H23A	0.9600
C12—C13	1.384 (3)	C23—H23B	0.9600
C13—C14	1.378 (3)	C23—H23C	0.9600
C13—H13	0.9300	O1—H1A	0.8200
C14—C15	1.371 (3)

N1—C1—C12	112.81 (15)	C14—C15—H15	120.1
N1—C1—C2	110.03 (15)	C15—C16—C17	120.2 (2)
C12—C1—C2	110.74 (15)	C15—C16—H16	119.9
N1—C1—H1	107.7	C17—C16—H16	119.9
C12—C1—H1	107.7	C16—C17—C12	120.7 (2)
C2—C1—H1	107.7	C16—C17—H17	119.6
C3—C2—C7	118.38 (18)	C12—C17—H17	119.6
C3—C2—C1	121.25 (17)	N1—C18—C19	109.91 (16)
C7—C2—C1	120.33 (17)	N1—C18—H18A	109.7
O1—C3—C2	123.06 (18)	C19—C18—H18A	109.7
O1—C3—C4	115.67 (18)	N1—C18—H18B	109.7
C2—C3—C4	121.3 (2)	C19—C18—H18B	109.7
C5—C4—C3	120.1 (2)	H18A—C18—H18B	108.2
C5—C4—H4	120.0	C20—C19—C18	112.10 (19)
C3—C4—H4	120.0	C20—C19—H19A	109.2
C4—C5—C6	121.6 (2)	C18—C19—H19A	109.2
C4—C5—H5	119.2	C20—C19—H19B	109.2
C6—C5—H5	119.2	C18—C19—H19B	109.2
C5—C6—C11	121.6 (2)	H19A—C19—H19B	107.9
C5—C6—C7	118.5 (2)	C19—C20—C21	110.91 (17)
C11—C6—C7	119.9 (2)	C19—C20—H20A	109.5
C6—C7—C8	116.79 (19)	C21—C20—H20A	109.5
C6—C7—C2	120.03 (19)	C19—C20—H20B	109.5
C8—C7—C2	123.18 (19)	C21—C20—H20B	109.5
C9—C8—C7	121.6 (2)	H20A—C20—H20B	108.0
C9—C8—H8	119.2	C20—C21—C23	112.82 (18)
C7—C8—H8	119.2	C20—C21—C22	109.29 (17)
C8—C9—C10	120.8 (3)	C23—C21—C22	110.02 (17)
C8—C9—H9	119.6	C20—C21—H21	108.2
C10—C9—H9	119.6	C23—C21—H21	108.2
C11—C10—C9	119.7 (2)	C22—C21—H21	108.2
C11—C10—H10	120.1	N1—C22—C21	112.21 (16)
C9—C10—H10	120.1	N1—C22—H22A	109.2
C10—C11—C6	121.2 (2)	C21—C22—H22A	109.2
C10—C11—H11	119.4	N1—C22—H22B	109.2
C6—C11—H11	119.4	C21—C22—H22B	109.2
C17—C12—C13	118.2 (2)	H22A—C22—H22B	107.9
C17—C12—C1	121.84 (17)	C21—C23—H23A	109.5
C13—C12—C1	119.93 (19)	C21—C23—H23B	109.5
C14—C13—C12	121.0 (2)	H23A—C23—H23B	109.5
C14—C13—H13	119.5	C21—C23—H23C	109.5
C12—C13—H13	119.5	H23A—C23—H23C	109.5
C15—C14—C13	120.1 (2)	H23B—C23—H23C	109.5
C15—C14—H14	120.0	C18—N1—C22	109.40 (15)
C13—C14—H14	120.0	C18—N1—C1	113.43 (14)
C16—C15—C14	119.8 (2)	C22—N1—C1	109.15 (14)
C16—C15—H15	120.1	C3—O1—H1A	109.5

N1—C1—C2—C3	−31.0 (2)	C7—C6—C11—C10	−1.1 (3)
C12—C1—C2—C3	94.4 (2)	N1—C1—C12—C17	63.6 (2)
N1—C1—C2—C7	151.44 (16)	C2—C1—C12—C17	−60.2 (2)
C12—C1—C2—C7	−83.2 (2)	N1—C1—C12—C13	−117.4 (2)
C7—C2—C3—O1	178.73 (17)	C2—C1—C12—C13	118.81 (19)
C1—C2—C3—O1	1.1 (3)	C17—C12—C13—C14	0.3 (3)
C7—C2—C3—C4	−1.6 (3)	C1—C12—C13—C14	−178.80 (18)
C1—C2—C3—C4	−179.21 (17)	C12—C13—C14—C15	−0.3 (3)
O1—C3—C4—C5	−177.90 (18)	C13—C14—C15—C16	0.2 (4)
C2—C3—C4—C5	2.4 (3)	C14—C15—C16—C17	0.0 (3)
C3—C4—C5—C6	−0.9 (3)	C15—C16—C17—C12	−0.1 (3)
C4—C5—C6—C11	179.4 (2)	C13—C12—C17—C16	0.0 (3)
C4—C5—C6—C7	−1.3 (3)	C1—C12—C17—C16	179.00 (18)
C5—C6—C7—C8	−178.04 (18)	N1—C18—C19—C20	−57.0 (3)
C11—C6—C7—C8	1.2 (3)	C18—C19—C20—C21	53.8 (3)
C5—C6—C7—C2	2.0 (3)	C19—C20—C21—C23	−175.32 (19)
C11—C6—C7—C2	−178.67 (17)	C19—C20—C21—C22	−52.6 (2)
C3—C2—C7—C6	−0.6 (3)	C20—C21—C22—N1	57.4 (2)
C1—C2—C7—C6	177.01 (17)	C23—C21—C22—N1	−178.25 (18)
C3—C2—C7—C8	179.47 (17)	C19—C18—N1—C22	59.5 (2)
C1—C2—C7—C8	−2.9 (3)	C19—C18—N1—C1	−178.37 (18)
C6—C7—C8—C9	−0.2 (3)	C21—C22—N1—C18	−61.3 (2)
C2—C7—C8—C9	179.68 (19)	C21—C22—N1—C1	174.09 (16)
C7—C8—C9—C10	−0.9 (3)	C12—C1—N1—C18	43.3 (2)
C8—C9—C10—C11	1.1 (4)	C2—C1—N1—C18	167.50 (16)
C9—C10—C11—C6	0.0 (4)	C12—C1—N1—C22	165.56 (15)
C5—C6—C11—C10	178.1 (2)	C2—C1—N1—C22	−70.23 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.84	2.570 (2)	148

Experimental details

Crystal data
Chemical formula	C₂₃H₂₅NO
M_r	331.44
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	292
a, b, c (Å)	9.2138 (13), 10.9056 (13), 18.635 (3)
β (°)	97.007 (10)
V (Å³)	1858.5 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.965, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	19217, 4422, 2302
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.155, 0.99
No. of reflections	4422
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL/PC (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	1.84	2.570 (2)	147.5

Acknowledgements

This work was supported by Young Researcher funds from Southeast University (grant No. 4007041027).

References

Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Szatmari, I. & Fulop, F. (2004). Curr. Org. Synth. 1, 155–165. Web of Science CrossRef CAS Google Scholar
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