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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2368.
Published online 2009 September 9. doi:  10.1107/S160053680903534X
PMCID: PMC2970458

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

Abstract

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

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 [triangle]). For the synthesis by the Skraup reaction of amino-9H-xanthene-9-one, see: Fujiwara & Okabayashi (1994 [triangle]).

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Object name is e-65-o2368-scheme1.jpg

Experimental

Crystal data

  • C16H9NO2·CH4O
  • M r = 279.28
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2368-efi1.jpg
  • a = 8.102 (2) Å
  • b = 8.791 (3) Å
  • c = 10.150 (3) Å
  • α = 102.172 (3)°
  • β = 108.760 (3)°
  • γ = 93.532 (3)°
  • V = 662.6 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 295 K
  • 0.41 × 0.30 × 0.18 mm

Data collection

  • Bruker APEXII diffractometer
  • Absorption correction: none
  • 3838 measured reflections
  • 2655 independent reflections
  • 1456 reflections with I > 2σ(I)
  • R int = 0.016

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.147
  • S = 1.02
  • 2655 reflections
  • 192 parameters
  • H-atom parameters constrained
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680903534X/xu2605sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903534X/xu2605Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Experimental

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

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)].

Figures

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.

Crystal data

C16H9NO2·CH4OZ = 2
Mr = 279.28F(000) = 292
Triclinic, P1Dx = 1.400 Mg m3
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 mm1
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

Bruker APEXII diffractometer1456 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.016
graphiteθmax = 26.5°, θmin = 2.2°
[var phi] and ω scansh = −10→10
3838 measured reflectionsk = −9→11
2655 independent reflectionsl = −12→12

Refinement

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 = 1.02w = 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 Å3
0 restraintsΔρmin = −0.15 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)

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, °)

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, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···N10.822.072.852 (2)160

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2605).

References

  • 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. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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