2-(2-p-Tolyl­benzo[g]quinolin-3-yl)ethanol

Wu, N.; Zhang, R.; Wang, Y.; Xu, X.; Xu, Z.

doi:10.1107/S1600536811038736

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2770

https://doi.org/10.1107/S1600536811038736

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2-(2-p-Tolylbenzo[g]quinolin-3-yl)ethanol

Nan Wu,^a Rongli Zhang,^b Yumei Wang,^a Xin Xu ^a and Zhou Xu ^b ^*

^aDepartment of Aviation Oil and Material, Xuzhou Airforce College, Xuzhou Jiangsu 221110, People's Republic of China, and ^bDeparement of Chemistry, Xuzhou Medical College, Xuzhou Jiangsu 221004, People's Republic of China
^*Correspondence e-mail: xuzhou@xzmc.edu.cn

(Received 5 August 2011; accepted 21 September 2011; online 30 September 2011)

In the title compound, C₂₂H₁₉NO, the pyridine ring and the adjacent naphthalene ring system are nearly coplanar, making a dihedral angle of 3.3 (1)°, while the pyridine and benzene rings are perpendicular to each other, with a dihedral angle of 89.9 (1)°. The crystal packing is stabilized by intermolecular O—H⋯N hydrogen bonds and C—H⋯π interactions.

Related literature

For the biological activity of quinoline derivatives, see: Faber et al. (1984 ); Johnson et al. (1989 ); Nesterova et al. (1995 ); Yamada et al. (1992 ).

Experimental

Crystal data

C₂₂H₁₉NO
M_r = 313.38
Triclinic, $[P \overline 1]$
a = 7.2044 (4) Å
b = 10.1704 (4) Å
c = 12.1194 (3) Å
α = 108.125 (3)°
β = 98.115 (4)°
γ = 99.370 (5)°
V = 815.08 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.49 × 0.21 × 0.07 mm

Data collection

Bruker APEXII area-detector diffractometer
10164 measured reflections
2879 independent reflections
2232 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.127
S = 1.03
2879 reflections
222 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N1,C1–C5 pyridine ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.93 (3)	1.98 (3)	2.9110 (18)	174 (2)
C21—H21A⋯Cgⁱⁱ	0.93	2.97	3.7358 (19)	140
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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 global, I. DOI: https://doi.org/10.1107/S1600536811038736/hg5076sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811038736/hg5076Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811038736/hg5076Isup3.cml

checkCIF report

Comment top

Quinoline derivatives possess varies of biological properties, such as psychotropic activity (Nesterova, et al., 1995), anti-allergic (Yamada et al., 1992) and anti-inflammatory activity (Faber et al., 1984 and Johnson et al., 1989). Therefore, the title compound (Fig. 1), may be used as a new precursor for obtaining bioactive molecules. Herein, we report the crystal structure of the title compound, (I).

In the crystal structure of (I), there are four aromatic rings and the pyridine ring is the new formed ring. The pyridine ring is a coplanar conformation. The pyridine ring and the adjacent naphthalene ring are nearly coplanar, with a dihedral angle of 3.3 (1)°. While the pyridine ring and the benzene ring are vertical with each other, with a dihedral angle of 89.9 (1)°. The molecules are connected by the O1—H1···N1 intermolecular hydrogen bond and C—H···π interactions (Figure 2). Besides, there is intermolecular π-π interaction between the two neighboring benzene rings (C4C5C6C7C8C13), symmetry code: (1-X, 2-Y, –Z). The two rings are parallel to each other. The centroid distance, plane-plane distance and displacement distance are 3.642, 3.499 and 1.010 Å, respectively, which strongly indicate the existence of intermolecular π-π interactions.

Related literature top

For the biological activity of quinoline derivatives, see: Faber et al. (1984); Johnson et al. (1989); Nesterova et al. (1995); Yamada et al. (1992).

Experimental top

The title compound, (I), was prepared by the reaction of 4-methylbenzaldehyde (0.240 g, 2.0 mmol), naphthalen-2-amine (0.286 g, 2.0 mmol) and I₂ (0.051 g, 0.2 mmol) in THF (10 ml) at reflux for 40 h (yield 86%, mp. 486–487 K). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a THF solution.

Structure description top

For the biological activity of quinoline derivatives, see: Faber et al. (1984); Johnson et al. (1989); Nesterova et al. (1995); Yamada et al. (1992).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 drawing shows 30% probability of displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The packing diagram of title compound viewed along the b axis. Dashed lines indicate hydrogen bonds of type O1—H1···N1 and C—H···π interactions.

2-(2-p-Tolylbenzo[g]quinolin-3-yl)ethanol top

Crystal data top

C₂₂H₁₉NO	Z = 2
M_r = 313.38	F(000) = 332
Triclinic, P1	D_x = 1.277 Mg m⁻³
Hall symbol: -P 1	Melting point = 486–487 K
a = 7.2044 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1704 (4) Å	Cell parameters from 3017 reflections
c = 12.1194 (3) Å	θ = 2.9–26.5°
α = 108.125 (3)°	µ = 0.08 mm⁻¹
β = 98.115 (4)°	T = 296 K
γ = 99.370 (5)°	Sheet, yellow
V = 815.08 (6) Å³	0.49 × 0.21 × 0.07 mm

Data collection top

Bruker APEXII area-detector diffractometer	2232 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.020
Graphite monochromator	θ_max = 25.0°, θ_min = 1.8°
phi and ω scans	h = −8→8
10164 measured reflections	k = −12→12
2879 independent reflections	l = −14→14

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0628P)² + 0.1533P] where P = (F_o² + 2F_c²)/3
2879 reflections	(Δ/σ)_max < 0.001
222 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₂H₁₉NO	γ = 99.370 (5)°
M_r = 313.38	V = 815.08 (6) Å³
Triclinic, P1	Z = 2
a = 7.2044 (4) Å	Mo Kα radiation
b = 10.1704 (4) Å	µ = 0.08 mm⁻¹
c = 12.1194 (3) Å	T = 296 K
α = 108.125 (3)°	0.49 × 0.21 × 0.07 mm
β = 98.115 (4)°

Data collection top

Bruker APEXII area-detector diffractometer	2232 reflections with I > 2σ(I)
10164 measured reflections	R_int = 0.020
2879 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.17 e Å⁻³
2879 reflections	Δρ_min = −0.16 e Å⁻³
222 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
O1	0.94638 (19)	0.74485 (14)	0.16847 (12)	0.0671 (4)
N1	0.34813 (18)	0.89390 (13)	0.23730 (12)	0.0473 (3)
C4	0.5880 (2)	1.05942 (15)	0.19621 (13)	0.0428 (4)
C5	0.3959 (2)	0.99592 (15)	0.18921 (13)	0.0442 (4)
C1	0.4871 (2)	0.84951 (15)	0.29047 (13)	0.0445 (4)
C3	0.7299 (2)	1.00948 (15)	0.25305 (14)	0.0462 (4)
H3A	0.8585	1.0487	0.2594	0.055*
C13	0.6286 (2)	1.16905 (15)	0.14470 (13)	0.0442 (4)
C6	0.2436 (2)	1.03711 (17)	0.12868 (15)	0.0532 (4)
H6A	0.1167	0.9958	0.1250	0.064*
C2	0.6844 (2)	0.90436 (15)	0.29965 (13)	0.0452 (4)
C8	0.4736 (2)	1.20451 (15)	0.08298 (13)	0.0478 (4)
C16	0.4202 (2)	0.73826 (16)	0.34132 (14)	0.0454 (4)
C9	0.5119 (3)	1.30789 (17)	0.03012 (15)	0.0580 (5)
H9A	0.4103	1.3303	−0.0115	0.070*
C7	0.2812 (2)	1.13509 (17)	0.07688 (15)	0.0552 (4)
H7A	0.1795	1.1583	0.0360	0.066*
C19	0.2814 (2)	0.52892 (18)	0.43403 (17)	0.0545 (4)
C14	0.8416 (2)	0.84739 (17)	0.35334 (15)	0.0537 (4)
H14A	0.9579	0.9215	0.3842	0.064*
H14B	0.8043	0.8229	0.4195	0.064*
C18	0.3153 (2)	0.49386 (18)	0.32095 (16)	0.0594 (5)
H18A	0.2917	0.3987	0.2741	0.071*
C17	0.3831 (3)	0.59584 (17)	0.27504 (15)	0.0561 (4)
H17A	0.4043	0.5683	0.1980	0.067*
C12	0.8149 (2)	1.24194 (17)	0.15198 (16)	0.0557 (4)
H12A	0.9188	1.2210	0.1929	0.067*
C11	0.8479 (3)	1.34320 (18)	0.10038 (17)	0.0647 (5)
H11A	0.9730	1.3902	0.1066	0.078*
C15	0.8844 (2)	0.71879 (18)	0.26679 (17)	0.0583 (5)
H15A	0.9832	0.6864	0.3079	0.070*
H15B	0.7695	0.6433	0.2384	0.070*
C21	0.3886 (3)	0.77368 (18)	0.45560 (16)	0.0628 (5)
H21A	0.4142	0.8686	0.5032	0.075*
C22	0.2070 (3)	0.4166 (2)	0.4833 (2)	0.0769 (6)
H22A	0.2832	0.3461	0.4697	0.115*
H22B	0.0756	0.3728	0.4446	0.115*
H22C	0.2147	0.4591	0.5669	0.115*
C10	0.6947 (3)	1.37576 (18)	0.03868 (16)	0.0641 (5)
H10A	0.7174	1.4442	0.0032	0.077*
C20	0.3197 (3)	0.6706 (2)	0.50019 (17)	0.0655 (5)
H20A	0.2985	0.6978	0.5772	0.079*
H1	1.074 (4)	0.793 (3)	0.196 (2)	0.111 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0505 (8)	0.0835 (9)	0.0729 (9)	0.0124 (6)	0.0160 (6)	0.0342 (7)
N1	0.0446 (7)	0.0461 (7)	0.0529 (8)	0.0092 (6)	0.0146 (6)	0.0176 (6)
C4	0.0459 (9)	0.0390 (7)	0.0424 (8)	0.0093 (6)	0.0116 (7)	0.0115 (6)
C5	0.0462 (9)	0.0418 (8)	0.0442 (9)	0.0108 (6)	0.0123 (7)	0.0122 (7)
C1	0.0457 (9)	0.0433 (8)	0.0445 (9)	0.0090 (7)	0.0133 (7)	0.0138 (7)
C3	0.0420 (8)	0.0455 (8)	0.0515 (9)	0.0058 (6)	0.0109 (7)	0.0185 (7)
C13	0.0518 (9)	0.0387 (8)	0.0414 (9)	0.0114 (7)	0.0109 (7)	0.0112 (6)
C6	0.0435 (9)	0.0544 (9)	0.0620 (11)	0.0125 (7)	0.0105 (8)	0.0196 (8)
C2	0.0467 (9)	0.0437 (8)	0.0458 (9)	0.0087 (7)	0.0107 (7)	0.0161 (7)
C8	0.0593 (10)	0.0411 (8)	0.0414 (9)	0.0149 (7)	0.0098 (7)	0.0101 (7)
C16	0.0404 (8)	0.0477 (8)	0.0503 (9)	0.0072 (6)	0.0123 (7)	0.0199 (7)
C9	0.0745 (12)	0.0502 (9)	0.0514 (10)	0.0205 (9)	0.0074 (9)	0.0196 (8)
C7	0.0532 (10)	0.0549 (9)	0.0581 (10)	0.0199 (8)	0.0059 (8)	0.0184 (8)
C19	0.0383 (8)	0.0633 (10)	0.0714 (12)	0.0083 (7)	0.0124 (8)	0.0373 (9)
C14	0.0480 (9)	0.0580 (10)	0.0600 (11)	0.0053 (7)	0.0062 (8)	0.0322 (8)
C18	0.0601 (11)	0.0470 (9)	0.0667 (12)	0.0011 (8)	0.0105 (9)	0.0200 (8)
C17	0.0647 (11)	0.0514 (9)	0.0492 (10)	0.0049 (8)	0.0133 (8)	0.0162 (8)
C12	0.0542 (10)	0.0522 (9)	0.0649 (11)	0.0081 (7)	0.0108 (8)	0.0283 (8)
C11	0.0668 (12)	0.0573 (10)	0.0725 (12)	0.0023 (9)	0.0126 (10)	0.0322 (9)
C15	0.0444 (9)	0.0620 (10)	0.0790 (12)	0.0120 (8)	0.0151 (9)	0.0373 (9)
C21	0.0784 (12)	0.0499 (9)	0.0585 (11)	0.0069 (8)	0.0286 (9)	0.0136 (8)
C22	0.0576 (11)	0.0869 (14)	0.1071 (17)	0.0101 (10)	0.0221 (11)	0.0628 (13)
C10	0.0861 (14)	0.0502 (9)	0.0610 (11)	0.0119 (9)	0.0129 (10)	0.0284 (9)
C20	0.0731 (12)	0.0716 (12)	0.0567 (11)	0.0087 (9)	0.0272 (9)	0.0264 (9)

Geometric parameters (Å, º) top

O1—C15	1.413 (2)	C7—H7A	0.9300
O1—H1	0.93 (3)	C19—C18	1.372 (3)
N1—C1	1.3294 (19)	C19—C20	1.373 (3)
N1—C5	1.3606 (19)	C19—C22	1.505 (2)
C4—C3	1.402 (2)	C14—C15	1.508 (2)
C4—C5	1.407 (2)	C14—H14A	0.9700
C4—C13	1.448 (2)	C14—H14B	0.9700
C5—C6	1.426 (2)	C18—C17	1.377 (2)
C1—C2	1.415 (2)	C18—H18A	0.9300
C1—C16	1.494 (2)	C17—H17A	0.9300
C3—C2	1.372 (2)	C12—C11	1.368 (2)
C3—H3A	0.9300	C12—H12A	0.9300
C13—C12	1.400 (2)	C11—C10	1.388 (3)
C13—C8	1.414 (2)	C11—H11A	0.9300
C6—C7	1.345 (2)	C15—H15A	0.9700
C6—H6A	0.9300	C15—H15B	0.9700
C2—C14	1.511 (2)	C21—C20	1.377 (2)
C8—C9	1.402 (2)	C21—H21A	0.9300
C8—C7	1.430 (2)	C22—H22A	0.9600
C16—C17	1.380 (2)	C22—H22B	0.9600
C16—C21	1.380 (2)	C22—H22C	0.9600
C9—C10	1.357 (3)	C10—H10A	0.9300
C9—H9A	0.9300	C20—H20A	0.9300

C15—O1—H1	105.8 (15)	C15—C14—H14A	108.9
C1—N1—C5	119.18 (13)	C2—C14—H14A	108.9
C3—C4—C5	116.48 (14)	C15—C14—H14B	108.9
C3—C4—C13	123.98 (14)	C2—C14—H14B	108.9
C5—C4—C13	119.54 (14)	H14A—C14—H14B	107.7
N1—C5—C4	122.42 (14)	C19—C18—C17	121.72 (16)
N1—C5—C6	117.78 (14)	C19—C18—H18A	119.1
C4—C5—C6	119.79 (14)	C17—C18—H18A	119.1
N1—C1—C2	122.65 (14)	C18—C17—C16	121.16 (16)
N1—C1—C16	115.17 (13)	C18—C17—H17A	119.4
C2—C1—C16	122.17 (14)	C16—C17—H17A	119.4
C2—C3—C4	121.90 (14)	C11—C12—C13	121.65 (17)
C2—C3—H3A	119.1	C11—C12—H12A	119.2
C4—C3—H3A	119.0	C13—C12—H12A	119.2
C12—C13—C8	117.79 (14)	C12—C11—C10	120.04 (18)
C12—C13—C4	123.31 (14)	C12—C11—H11A	120.0
C8—C13—C4	118.90 (14)	C10—C11—H11A	120.0
C7—C6—C5	120.72 (15)	O1—C15—C14	113.27 (14)
C7—C6—H6A	119.6	O1—C15—H15A	108.9
C5—C6—H6A	119.6	C14—C15—H15A	108.9
C3—C2—C1	117.33 (14)	O1—C15—H15B	108.9
C3—C2—C14	120.10 (14)	C14—C15—H15B	108.9
C1—C2—C14	122.52 (13)	H15A—C15—H15B	107.7
C9—C8—C13	119.27 (15)	C20—C21—C16	121.03 (16)
C9—C8—C7	121.50 (15)	C20—C21—H21A	119.5
C13—C8—C7	119.23 (14)	C16—C21—H21A	119.5
C17—C16—C21	117.21 (15)	C19—C22—H22A	109.5
C17—C16—C1	121.38 (14)	C19—C22—H22B	109.5
C21—C16—C1	121.40 (14)	H22A—C22—H22B	109.5
C10—C9—C8	121.18 (16)	C19—C22—H22C	109.5
C10—C9—H9A	119.4	H22A—C22—H22C	109.5
C8—C9—H9A	119.4	H22B—C22—H22C	109.5
C6—C7—C8	121.74 (15)	C9—C10—C11	120.07 (16)
C6—C7—H7A	119.1	C9—C10—H10A	120.0
C8—C7—H7A	119.1	C11—C10—H10A	120.0
C18—C19—C20	117.08 (15)	C19—C20—C21	121.80 (17)
C18—C19—C22	121.27 (17)	C19—C20—H20A	119.1
C20—C19—C22	121.65 (17)	C21—C20—H20A	119.1
C15—C14—C2	113.54 (14)

C1—N1—C5—C4	−1.7 (2)	C2—C1—C16—C17	−90.9 (2)
C1—N1—C5—C6	177.53 (13)	N1—C1—C16—C21	−88.66 (19)
C3—C4—C5—N1	1.6 (2)	C2—C1—C16—C21	90.7 (2)
C13—C4—C5—N1	−179.01 (13)	C13—C8—C9—C10	−1.0 (2)
C3—C4—C5—C6	−177.56 (13)	C7—C8—C9—C10	178.41 (15)
C13—C4—C5—C6	1.8 (2)	C5—C6—C7—C8	−1.8 (3)
C5—N1—C1—C2	0.2 (2)	C9—C8—C7—C6	−179.16 (15)
C5—N1—C1—C16	179.51 (12)	C13—C8—C7—C6	0.2 (2)
C5—C4—C3—C2	−0.1 (2)	C3—C2—C14—C15	−92.86 (18)
C13—C4—C3—C2	−179.40 (13)	C1—C2—C14—C15	84.48 (19)
C3—C4—C13—C12	−3.5 (2)	C20—C19—C18—C17	−0.5 (3)
C5—C4—C13—C12	177.21 (14)	C22—C19—C18—C17	179.92 (16)
C3—C4—C13—C8	176.03 (13)	C19—C18—C17—C16	0.1 (3)
C5—C4—C13—C8	−3.3 (2)	C21—C16—C17—C18	0.7 (3)
N1—C5—C6—C7	−178.50 (14)	C1—C16—C17—C18	−177.77 (15)
C4—C5—C6—C7	0.7 (2)	C8—C13—C12—C11	−0.7 (2)
C4—C3—C2—C1	−1.3 (2)	C4—C13—C12—C11	178.83 (15)
C4—C3—C2—C14	176.17 (14)	C13—C12—C11—C10	−0.1 (3)
N1—C1—C2—C3	1.3 (2)	C2—C14—C15—O1	60.50 (18)
C16—C1—C2—C3	−177.99 (13)	C17—C16—C21—C20	−1.1 (3)
N1—C1—C2—C14	−176.11 (14)	C1—C16—C21—C20	177.39 (17)
C16—C1—C2—C14	4.6 (2)	C8—C9—C10—C11	0.1 (3)
C12—C13—C8—C9	1.2 (2)	C12—C11—C10—C9	0.4 (3)
C4—C13—C8—C9	−178.32 (13)	C18—C19—C20—C21	0.1 (3)
C12—C13—C8—C7	−178.16 (14)	C22—C19—C20—C21	179.70 (17)
C4—C13—C8—C7	2.3 (2)	C16—C21—C20—C19	0.7 (3)
N1—C1—C16—C17	89.77 (18)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the N1,C1–C5 pyridine ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.93 (3)	1.98 (3)	2.9110 (18)	174 (2)
C21—H21A···Cgⁱⁱ	0.93	2.97	3.7358 (19)	140

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₉NO
M_r	313.38
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.2044 (4), 10.1704 (4), 12.1194 (3)
α, β, γ (°)	108.125 (3), 98.115 (4), 99.370 (5)
V (Å³)	815.08 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.49 × 0.21 × 0.07

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10164, 2879, 2232
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.127, 1.03
No. of reflections	2879
No. of parameters	222
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.16

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the N1,C1–C5 pyridine ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.93 (3)	1.98 (3)	2.9110 (18)	174 (2)
C21—H21A···Cgⁱⁱ	0.93	2.97	3.7358 (19)	140.0

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

Acknowledgements

We are grateful to the Special Presidential Foundation of Xuzhou Medical College (2010KJZ15) for financial support. We thank Su Hong of Zhejiang Normal University for the data collection.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Faber, K., Stueckler, H. & Kappe, T. (1984). J. Heterocycl. Chem. 21, 1177–1178. CrossRef CAS Google Scholar
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Nesterova, I., Alekseeva, L. M., Andreeva, L. M., Andreeva, N. I., Golovira, S. M. & Granic, V. G. (1995). Khim. Farm. Zh. 29, 31–34. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yamada, N., Kadowaki, S., Takahashi, K. & Umezu, K. (1992). Biochem. Pharmacol. 44, 1211–1213. CrossRef PubMed CAS Web of Science Google Scholar

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