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Acta Cryst. (2009). E65, o2368    [ doi:10.1107/S160053680903534X ]

7H-Chromeno[3,2-h]quinolin-7-one methanol monosolvate

J.-K. Qin, Z.-M. Yang, M.-H. Zeng and S. W. Ng

Abstract top

The four-ring system in the title compound, C16H9NO2·CH3OH, is planar (r.m.s deviation = 0.03 Å); the methanol solvent molecule forms a hydrogen bond to the quinoline N atom.

Related literature top

The compound in this study was synthesized from the cyclization of 2-(quinolin-8-yloxy)benzoic acid; for the synthesis of this acid, see: Chen et al. (2007). For the synthesis by the Skraup reaction of amino-9H-xanthene-9-one, see: Fujiwara & Okabayashi (1994).

Experimental top

2-(Quinolin-8-yloxy)benzoic acid was synthesized by using a literature procedure (Chen et al., 2007). The carboxylic acid (0.5 g) and polyphosphoric acid (3.5 g) were heated at 413 K for two hours; the reaction was monitored by thin layer chromatography. The hot mixture was poured into ice water (200 ml); the pH value of the solution was adjusted to 7–8 by concentrated ammonium hydroxide. The crude product that precipitated was collected and recrystallized from methanol (in 0.39 g yield). The formulation was established by 1H NMR spectral integral analysis.

Refinement top

Carbon- and oxygen-bound hydrogen atoms were generated geometrically and were constrained to ride on their parent atoms [C–H = 0.93–0.96, O–H 0.82 Å; Uiso(H) =1.2–1.5Ueq(C,O)].

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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C16H9NO2.CH4O at the 50% probability level; hydrogen atoms are drawn as sphere of arbitrary radius. The dashed line denotes a hydrogen bond.
7H-Chromeno[3,2-h]quinolin-7-one methanol monosolvate top
Crystal data top
C16H9NO2·CH4OZ = 2
Mr = 279.28F(000) = 292
Triclinic, P1Dx = 1.400 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.102 (2) ÅCell parameters from 1000 reflections
b = 8.791 (3) Åθ = 2.2–26.5°
c = 10.150 (3) ŵ = 0.10 mm−1
α = 102.172 (3)°T = 295 K
β = 108.760 (3)°Block, yellow
γ = 93.532 (3)°0.41 × 0.30 × 0.18 mm
V = 662.6 (3) Å3
Data collection top
Bruker APEXII
diffractometer		1456 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.016
graphiteθmax = 26.5°, θmin = 2.2°
φ and ω scansh = −10→10
3838 measured reflectionsk = −9→11
2655 independent reflectionsl = −12→12
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0688P)2 + 0.0458P]
where P = (Fo2 + 2Fc2)/3
2655 reflections(Δ/σ)max = 0.001
192 parametersΔρmax = 0.22 e Å−3
0 restraintsΔρmin = −0.15 e Å−3
Crystal data top
C16H9NO2·CH4Oγ = 93.532 (3)°
Mr = 279.28V = 662.6 (3) Å3
Triclinic, P1Z = 2
a = 8.102 (2) ÅMo Kα radiation
b = 8.791 (3) ŵ = 0.10 mm−1
c = 10.150 (3) ÅT = 295 K
α = 102.172 (3)°0.41 × 0.30 × 0.18 mm
β = 108.760 (3)°
Data collection top
Bruker APEXII
diffractometer		Rint = 0.016
3838 measured reflectionsθmax = 26.5°
2655 independent reflectionsStandard reflections: 0
1456 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.147Δρmax = 0.22 e Å−3
S = 1.02Δρmin = −0.15 e Å−3
2655 reflectionsAbsolute structure: ?
192 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.25297 (18)0.41753 (15)0.57244 (14)0.0387 (4)
O20.2583 (2)0.64419 (19)0.25985 (17)0.0601 (5)
O30.2226 (2)0.2382 (2)0.8300 (2)0.0735 (6)
H30.19460.31700.80210.110*
N10.1800 (2)0.5518 (2)0.80538 (18)0.0402 (5)
C10.2905 (3)0.3418 (2)0.4545 (2)0.0359 (5)
C20.3238 (3)0.1887 (3)0.4504 (2)0.0449 (6)
H20.32040.14270.52420.054*
C30.3619 (3)0.1058 (3)0.3359 (3)0.0506 (6)
H3a0.38390.00270.33180.061*
C40.3680 (3)0.1741 (3)0.2259 (3)0.0535 (6)
H40.39430.11690.14890.064*
C50.3353 (3)0.3254 (3)0.2310 (2)0.0475 (6)
H50.33980.37060.15700.057*
C60.2950 (3)0.4136 (2)0.3461 (2)0.0374 (5)
C70.2553 (3)0.5754 (2)0.3526 (2)0.0401 (5)
C80.2134 (2)0.6488 (2)0.4794 (2)0.0341 (5)
C90.1720 (3)0.8044 (2)0.4991 (2)0.0429 (6)
H90.16530.85790.42800.052*
C100.1423 (3)0.8764 (3)0.6186 (3)0.0445 (6)
H100.11820.97950.63010.053*
C110.1473 (3)0.7963 (2)0.7271 (2)0.0372 (5)
C120.1185 (3)0.8653 (3)0.8556 (3)0.0487 (6)
H120.09840.96940.87380.058*
C130.1204 (3)0.7792 (3)0.9517 (3)0.0521 (6)
H130.10230.82371.03670.063*
C140.1498 (3)0.6225 (3)0.9221 (2)0.0476 (6)
H140.14810.56460.98860.057*
C150.1802 (2)0.6383 (2)0.7082 (2)0.0341 (5)
C160.2159 (3)0.5678 (2)0.5817 (2)0.0326 (5)
C170.4047 (4)0.2427 (3)0.8712 (3)0.0733 (8)
H17A0.44570.27840.80260.110*
H17B0.43450.13940.87540.110*
H17C0.45940.31350.96410.110*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0529 (10)0.0317 (8)0.0361 (9)0.0084 (7)0.0207 (7)0.0087 (6)
O20.0888 (13)0.0568 (11)0.0475 (10)0.0125 (9)0.0329 (10)0.0240 (8)
O30.0733 (14)0.0473 (11)0.1034 (17)0.0123 (9)0.0283 (12)0.0276 (10)
N10.0469 (11)0.0408 (11)0.0351 (11)0.0057 (8)0.0163 (9)0.0102 (8)
C10.0344 (12)0.0363 (12)0.0334 (12)0.0019 (9)0.0112 (10)0.0025 (9)
C20.0480 (14)0.0386 (13)0.0490 (14)0.0068 (10)0.0187 (12)0.0094 (11)
C30.0538 (15)0.0383 (13)0.0572 (16)0.0093 (11)0.0207 (13)0.0025 (11)
C40.0523 (16)0.0563 (16)0.0487 (16)0.0073 (12)0.0223 (13)−0.0019 (12)
C50.0496 (15)0.0523 (15)0.0401 (14)0.0034 (11)0.0183 (11)0.0067 (11)
C60.0344 (12)0.0396 (12)0.0352 (13)−0.0005 (9)0.0116 (10)0.0048 (10)
C70.0407 (13)0.0429 (13)0.0345 (13)−0.0020 (10)0.0108 (10)0.0103 (10)
C80.0324 (12)0.0331 (11)0.0343 (12)−0.0001 (9)0.0092 (10)0.0077 (9)
C90.0492 (14)0.0376 (12)0.0457 (14)0.0065 (10)0.0169 (11)0.0168 (10)
C100.0478 (14)0.0315 (12)0.0561 (15)0.0088 (10)0.0190 (12)0.0119 (11)
C110.0330 (12)0.0337 (12)0.0412 (13)0.0023 (9)0.0113 (10)0.0039 (9)
C120.0506 (15)0.0396 (13)0.0528 (15)0.0104 (11)0.0195 (12)0.0009 (11)
C130.0600 (16)0.0543 (15)0.0422 (14)0.0091 (12)0.0243 (13)0.0010 (12)
C140.0549 (15)0.0543 (15)0.0368 (13)0.0071 (12)0.0193 (12)0.0122 (11)
C150.0305 (12)0.0351 (12)0.0342 (12)0.0012 (9)0.0087 (9)0.0081 (9)
C160.0323 (12)0.0285 (11)0.0349 (12)0.0017 (9)0.0105 (9)0.0056 (9)
C170.077 (2)0.080 (2)0.069 (2)0.0168 (16)0.0302 (17)0.0195 (16)
Geometric parameters (Å, °) top
O1—C161.363 (2)C7—C81.466 (3)
O1—C11.375 (2)C8—C161.373 (3)
O2—C71.227 (2)C8—C91.417 (3)
O3—C171.394 (3)C9—C101.347 (3)
O3—H30.8200C9—H90.9300
N1—C141.321 (3)C10—C111.419 (3)
N1—C151.367 (2)C10—H100.9300
C1—C21.384 (3)C11—C151.415 (3)
C1—C61.388 (3)C11—C121.415 (3)
C2—C31.371 (3)C12—C131.352 (3)
C2—H20.9300C12—H120.9300
C3—C41.386 (3)C13—C141.399 (3)
C3—H3a0.9300C13—H130.9300
C4—C51.366 (3)C14—H140.9300
C4—H40.9300C15—C161.429 (3)
C5—C61.403 (3)C17—H17A0.9600
C5—H50.9300C17—H17B0.9600
C6—C71.470 (3)C17—H17C0.9600
C16—O1—C1118.65 (15)C8—C9—H9119.3
C17—O3—H3109.5C9—C10—C11120.6 (2)
C14—N1—C15117.14 (18)C9—C10—H10119.7
O1—C1—C2115.76 (18)C11—C10—H10119.7
O1—C1—C6122.41 (18)C15—C11—C12116.89 (19)
C2—C1—C6121.82 (19)C15—C11—C10119.7 (2)
C3—C2—C1119.0 (2)C12—C11—C10123.4 (2)
C3—C2—H2120.5C13—C12—C11119.7 (2)
C1—C2—H2120.5C13—C12—H12120.2
C2—C3—C4120.7 (2)C11—C12—H12120.2
C2—C3—H3a119.6C12—C13—C14119.4 (2)
C4—C3—H3a119.6C12—C13—H13120.3
C5—C4—C3119.9 (2)C14—C13—H13120.3
C5—C4—H4120.0N1—C14—C13123.9 (2)
C3—C4—H4120.0N1—C14—H14118.0
C4—C5—C6121.0 (2)C13—C14—H14118.0
C4—C5—H5119.5N1—C15—C11122.95 (19)
C6—C5—H5119.5N1—C15—C16119.13 (18)
C1—C6—C5117.6 (2)C11—C15—C16117.92 (18)
C1—C6—C7120.34 (19)O1—C16—C8123.74 (18)
C5—C6—C7122.08 (19)O1—C16—C15115.04 (16)
O2—C7—C8122.5 (2)C8—C16—C15121.22 (18)
O2—C7—C6122.8 (2)O3—C17—H17A109.5
C8—C7—C6114.67 (18)O3—C17—H17B109.5
C16—C8—C9119.21 (19)H17A—C17—H17B109.5
C16—C8—C7120.17 (18)O3—C17—H17C109.5
C9—C8—C7120.62 (18)H17A—C17—H17C109.5
C10—C9—C8121.3 (2)H17B—C17—H17C109.5
C10—C9—H9119.3
C16—O1—C1—C2−178.86 (17)C9—C10—C11—C15−1.3 (3)
C16—O1—C1—C61.1 (3)C9—C10—C11—C12179.5 (2)
O1—C1—C2—C3179.87 (19)C15—C11—C12—C13−1.1 (3)
C6—C1—C2—C3−0.1 (3)C10—C11—C12—C13178.0 (2)
C1—C2—C3—C40.3 (3)C11—C12—C13—C14−0.4 (4)
C2—C3—C4—C5−0.2 (4)C15—N1—C14—C13−0.6 (3)
C3—C4—C5—C6−0.1 (4)C12—C13—C14—N11.4 (4)
O1—C1—C6—C5179.83 (19)C14—N1—C15—C11−1.0 (3)
C2—C1—C6—C5−0.2 (3)C14—N1—C15—C16178.70 (19)
O1—C1—C6—C7−1.3 (3)C12—C11—C15—N11.9 (3)
C2—C1—C6—C7178.69 (19)C10—C11—C15—N1−177.29 (19)
C4—C5—C6—C10.3 (3)C12—C11—C15—C16−177.82 (18)
C4—C5—C6—C7−178.6 (2)C10—C11—C15—C163.0 (3)
C1—C6—C7—O2179.7 (2)C1—O1—C16—C80.2 (3)
C5—C6—C7—O2−1.5 (3)C1—O1—C16—C15−179.36 (16)
C1—C6—C7—C80.2 (3)C9—C8—C16—O1179.58 (18)
C5—C6—C7—C8179.03 (19)C7—C8—C16—O1−1.2 (3)
O2—C7—C8—C16−178.4 (2)C9—C8—C16—C15−0.9 (3)
C6—C7—C8—C161.0 (3)C7—C8—C16—C15178.25 (19)
O2—C7—C8—C90.7 (3)N1—C15—C16—O1−2.1 (3)
C6—C7—C8—C9−179.84 (18)C11—C15—C16—O1177.68 (17)
C16—C8—C9—C102.7 (3)N1—C15—C16—C8178.38 (18)
C7—C8—C9—C10−176.5 (2)C11—C15—C16—C8−1.9 (3)
C8—C9—C10—C11−1.6 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3···N10.822.072.852 (2)160
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3···N10.822.072.852 (2)160
Acknowledgements top

This work was supported by Guangxi Natural Science Foundation (No.0639030), the Guangxi Normal University Foundation and the University of Malaya.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2004). APEX2 and SAINT. Bruker AXS inc., Madison, Wisconsin, USA.

Chen, Q., Qin, J.-K., Zeng, M.-H. & Ng, S. W. (2007). Acta Cryst. E63, o453–o454.

Fujiwara, H. & Okabayashi, I. (1994). Heterocycles, 38, 541–550.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2009). publCIF. In preparation.