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organic compounds
2-(2-p-Tolylbenzo[g]quinolin-3-yl)ethanol
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
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
|
Data collection
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2004); cell 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
https://doi.org/10.1107/S1600536811038736/hg5076sup1.cif
contains datablocks global, I. DOI: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
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.
The hydrogen atom of hydroxy group, was positioned from a Fourier difference map and was refined freely. Other H atoms were placed in calculated positions, with C—H = 0.93–0.98 Å, and with Uiso(H) = 1.2Ueq(parent atom).
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
of the title compound, (I).In the 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.
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···For the biological activity of quinoline derivatives, see: Faber et al. (1984); Johnson et al. (1989); Nesterova et al. (1995); Yamada et al. (1992).
Data collection: APEX2 (Bruker, 2004); cell
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).C22H19NO | Z = 2 |
Mr = 313.38 | F(000) = 332 |
Triclinic, P1 | Dx = 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 |
Bruker APEXII area-detector diffractometer | 2232 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 25.0°, θmin = 1.8° |
phi and ω scans | h = −8→8 |
10164 measured reflections | k = −12→12 |
2879 independent reflections | l = −14→14 |
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(Fo2) + (0.0628P)2 + 0.1533P] where P = (Fo2 + 2Fc2)/3 |
2879 reflections | (Δ/σ)max < 0.001 |
222 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C22H19NO | γ = 99.370 (5)° |
Mr = 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)° |
Bruker APEXII area-detector diffractometer | 2232 reflections with I > 2σ(I) |
10164 measured reflections | Rint = 0.020 |
2879 independent reflections |
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 | Δρmax = 0.17 e Å−3 |
2879 reflections | Δρmin = −0.16 e Å−3 |
222 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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)* |
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) |
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) |
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 |
Mr | 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 |
Rint | 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 |
Δρmax, Δρmin (e Å−3) | 0.17, −0.16 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
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
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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.