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

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

doi:10.1107/S160053680903534X

organic compounds

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Volume 65| Part 10| October 2009| Page o2368

doi:10.1107/S160053680903534X

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

Jiang-Ke Qin,^a Zheng-Min Yang,^a Ming-Hua Zeng ^a and Seik Weng Ng ^b ^*

^aKey Laboratory for the Chemistry & Molecular Engineering of Medicinal Resources, (Ministry of Education of China), School of Chemistry & Chemical Engineering, Guangxi Normal University, 541004 Guilin 541004, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 1 September 2009; accepted 1 September 2009; online 9 September 2009)

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

Experimental

Crystal data

C₁₆H₉NO₂·CH₄O
M_r = 279.28
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.046
wR(F²) = 0.147
S = 1.02
2655 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N1	0.82	2.07	2.852 (2)	160

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

Supporting information

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

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

checkCIF report

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.

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

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·CH₄O	Z = 2
M_r = 279.28	F(000) = 292
Triclinic, P1	D_x = 1.400 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.102 (2) Å	Cell parameters from 1000 reflections
b = 8.791 (3) Å	θ = 2.2–26.5°
c = 10.150 (3) Å	µ = 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 tube	R_int = 0.016
Graphite monochromator	θ_max = 26.5°, θ_min = 2.2°
ϕ and ω scans	h = −10→10
3838 measured reflections	k = −9→11
2655 independent reflections	l = −12→12

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0688P)² + 0.0458P] where P = (F_o² + 2F_c²)/3
2655 reflections	(Δ/σ)_max = 0.001
192 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₆H₉NO₂·CH₄O	γ = 93.532 (3)°
M_r = 279.28	V = 662.6 (3) Å³
Triclinic, P1	Z = 2
a = 8.102 (2) Å	Mo Kα radiation
b = 8.791 (3) Å	µ = 0.10 mm⁻¹
c = 10.150 (3) Å	T = 295 K
α = 102.172 (3)°	0.41 × 0.30 × 0.18 mm
β = 108.760 (3)°

Data collection top

Bruker APEXII diffractometer	1456 reflections with I > 2σ(I)
3838 measured reflections	R_int = 0.016
2655 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.147	H-atom parameters constrained
S = 1.02	Δρ_max = 0.22 e Å⁻³
2655 reflections	Δρ_min = −0.15 e Å⁻³
192 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.25297 (18)	0.41753 (15)	0.57244 (14)	0.0387 (4)
O2	0.2583 (2)	0.64419 (19)	0.25985 (17)	0.0601 (5)
O3	0.2226 (2)	0.2382 (2)	0.8300 (2)	0.0735 (6)
H3	0.1946	0.3170	0.8021	0.110*
N1	0.1800 (2)	0.5518 (2)	0.80538 (18)	0.0402 (5)
C1	0.2905 (3)	0.3418 (2)	0.4545 (2)	0.0359 (5)
C2	0.3238 (3)	0.1887 (3)	0.4504 (2)	0.0449 (6)
H2	0.3204	0.1427	0.5242	0.054*
C3	0.3619 (3)	0.1058 (3)	0.3359 (3)	0.0506 (6)
H3a	0.3839	0.0027	0.3318	0.061*
C4	0.3680 (3)	0.1741 (3)	0.2259 (3)	0.0535 (6)
H4	0.3943	0.1169	0.1489	0.064*
C5	0.3353 (3)	0.3254 (3)	0.2310 (2)	0.0475 (6)
H5	0.3398	0.3706	0.1570	0.057*
C6	0.2950 (3)	0.4136 (2)	0.3461 (2)	0.0374 (5)
C7	0.2553 (3)	0.5754 (2)	0.3526 (2)	0.0401 (5)
C8	0.2134 (2)	0.6488 (2)	0.4794 (2)	0.0341 (5)
C9	0.1720 (3)	0.8044 (2)	0.4991 (2)	0.0429 (6)
H9	0.1653	0.8579	0.4280	0.052*
C10	0.1423 (3)	0.8764 (3)	0.6186 (3)	0.0445 (6)
H10	0.1182	0.9795	0.6301	0.053*
C11	0.1473 (3)	0.7963 (2)	0.7271 (2)	0.0372 (5)
C12	0.1185 (3)	0.8653 (3)	0.8556 (3)	0.0487 (6)
H12	0.0984	0.9694	0.8738	0.058*
C13	0.1204 (3)	0.7792 (3)	0.9517 (3)	0.0521 (6)
H13	0.1023	0.8237	1.0367	0.063*
C14	0.1498 (3)	0.6225 (3)	0.9221 (2)	0.0476 (6)
H14	0.1481	0.5646	0.9886	0.057*
C15	0.1802 (2)	0.6383 (2)	0.7082 (2)	0.0341 (5)
C16	0.2159 (3)	0.5678 (2)	0.5817 (2)	0.0326 (5)
C17	0.4047 (4)	0.2427 (3)	0.8712 (3)	0.0733 (8)
H17A	0.4457	0.2784	0.8026	0.110*
H17B	0.4345	0.1394	0.8754	0.110*
H17C	0.4594	0.3135	0.9641	0.110*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0529 (10)	0.0317 (8)	0.0361 (9)	0.0084 (7)	0.0207 (7)	0.0087 (6)
O2	0.0888 (13)	0.0568 (11)	0.0475 (10)	0.0125 (9)	0.0329 (10)	0.0240 (8)
O3	0.0733 (14)	0.0473 (11)	0.1034 (17)	0.0123 (9)	0.0283 (12)	0.0276 (10)
N1	0.0469 (11)	0.0408 (11)	0.0351 (11)	0.0057 (8)	0.0163 (9)	0.0102 (8)
C1	0.0344 (12)	0.0363 (12)	0.0334 (12)	0.0019 (9)	0.0112 (10)	0.0025 (9)
C2	0.0480 (14)	0.0386 (13)	0.0490 (14)	0.0068 (10)	0.0187 (12)	0.0094 (11)
C3	0.0538 (15)	0.0383 (13)	0.0572 (16)	0.0093 (11)	0.0207 (13)	0.0025 (11)
C4	0.0523 (16)	0.0563 (16)	0.0487 (16)	0.0073 (12)	0.0223 (13)	−0.0019 (12)
C5	0.0496 (15)	0.0523 (15)	0.0401 (14)	0.0034 (11)	0.0183 (11)	0.0067 (11)
C6	0.0344 (12)	0.0396 (12)	0.0352 (13)	−0.0005 (9)	0.0116 (10)	0.0048 (10)
C7	0.0407 (13)	0.0429 (13)	0.0345 (13)	−0.0020 (10)	0.0108 (10)	0.0103 (10)
C8	0.0324 (12)	0.0331 (11)	0.0343 (12)	−0.0001 (9)	0.0092 (10)	0.0077 (9)
C9	0.0492 (14)	0.0376 (12)	0.0457 (14)	0.0065 (10)	0.0169 (11)	0.0168 (10)
C10	0.0478 (14)	0.0315 (12)	0.0561 (15)	0.0088 (10)	0.0190 (12)	0.0119 (11)
C11	0.0330 (12)	0.0337 (12)	0.0412 (13)	0.0023 (9)	0.0113 (10)	0.0039 (9)
C12	0.0506 (15)	0.0396 (13)	0.0528 (15)	0.0104 (11)	0.0195 (12)	0.0009 (11)
C13	0.0600 (16)	0.0543 (15)	0.0422 (14)	0.0091 (12)	0.0243 (13)	0.0010 (12)
C14	0.0549 (15)	0.0543 (15)	0.0368 (13)	0.0071 (12)	0.0193 (12)	0.0122 (11)
C15	0.0305 (12)	0.0351 (12)	0.0342 (12)	0.0012 (9)	0.0087 (9)	0.0081 (9)
C16	0.0323 (12)	0.0285 (11)	0.0349 (12)	0.0017 (9)	0.0105 (9)	0.0056 (9)
C17	0.077 (2)	0.080 (2)	0.069 (2)	0.0168 (16)	0.0302 (17)	0.0195 (16)

Geometric parameters (Å, º) top

O1—C16	1.363 (2)	C7—C8	1.466 (3)
O1—C1	1.375 (2)	C8—C16	1.373 (3)
O2—C7	1.227 (2)	C8—C9	1.417 (3)
O3—C17	1.394 (3)	C9—C10	1.347 (3)
O3—H3	0.8200	C9—H9	0.9300
N1—C14	1.321 (3)	C10—C11	1.419 (3)
N1—C15	1.367 (2)	C10—H10	0.9300
C1—C2	1.384 (3)	C11—C15	1.415 (3)
C1—C6	1.388 (3)	C11—C12	1.415 (3)
C2—C3	1.371 (3)	C12—C13	1.352 (3)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.386 (3)	C13—C14	1.399 (3)
C3—H3a	0.9300	C13—H13	0.9300
C4—C5	1.366 (3)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.429 (3)
C5—C6	1.403 (3)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—C7	1.470 (3)	C17—H17C	0.9600

C16—O1—C1	118.65 (15)	C8—C9—H9	119.3
C17—O3—H3	109.5	C9—C10—C11	120.6 (2)
C14—N1—C15	117.14 (18)	C9—C10—H10	119.7
O1—C1—C2	115.76 (18)	C11—C10—H10	119.7
O1—C1—C6	122.41 (18)	C15—C11—C12	116.89 (19)
C2—C1—C6	121.82 (19)	C15—C11—C10	119.7 (2)
C3—C2—C1	119.0 (2)	C12—C11—C10	123.4 (2)
C3—C2—H2	120.5	C13—C12—C11	119.7 (2)
C1—C2—H2	120.5	C13—C12—H12	120.2
C2—C3—C4	120.7 (2)	C11—C12—H12	120.2
C2—C3—H3a	119.6	C12—C13—C14	119.4 (2)
C4—C3—H3a	119.6	C12—C13—H13	120.3
C5—C4—C3	119.9 (2)	C14—C13—H13	120.3
C5—C4—H4	120.0	N1—C14—C13	123.9 (2)
C3—C4—H4	120.0	N1—C14—H14	118.0
C4—C5—C6	121.0 (2)	C13—C14—H14	118.0
C4—C5—H5	119.5	N1—C15—C11	122.95 (19)
C6—C5—H5	119.5	N1—C15—C16	119.13 (18)
C1—C6—C5	117.6 (2)	C11—C15—C16	117.92 (18)
C1—C6—C7	120.34 (19)	O1—C16—C8	123.74 (18)
C5—C6—C7	122.08 (19)	O1—C16—C15	115.04 (16)
O2—C7—C8	122.5 (2)	C8—C16—C15	121.22 (18)
O2—C7—C6	122.8 (2)	O3—C17—H17A	109.5
C8—C7—C6	114.67 (18)	O3—C17—H17B	109.5
C16—C8—C9	119.21 (19)	H17A—C17—H17B	109.5
C16—C8—C7	120.17 (18)	O3—C17—H17C	109.5
C9—C8—C7	120.62 (18)	H17A—C17—H17C	109.5
C10—C9—C8	121.3 (2)	H17B—C17—H17C	109.5
C10—C9—H9	119.3

C16—O1—C1—C2	−178.86 (17)	C9—C10—C11—C15	−1.3 (3)
C16—O1—C1—C6	1.1 (3)	C9—C10—C11—C12	179.5 (2)
O1—C1—C2—C3	179.87 (19)	C15—C11—C12—C13	−1.1 (3)
C6—C1—C2—C3	−0.1 (3)	C10—C11—C12—C13	178.0 (2)
C1—C2—C3—C4	0.3 (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—N1	1.4 (4)
O1—C1—C6—C5	179.83 (19)	C14—N1—C15—C11	−1.0 (3)
C2—C1—C6—C5	−0.2 (3)	C14—N1—C15—C16	178.70 (19)
O1—C1—C6—C7	−1.3 (3)	C12—C11—C15—N1	1.9 (3)
C2—C1—C6—C7	178.69 (19)	C10—C11—C15—N1	−177.29 (19)
C4—C5—C6—C1	0.3 (3)	C12—C11—C15—C16	−177.82 (18)
C4—C5—C6—C7	−178.6 (2)	C10—C11—C15—C16	3.0 (3)
C1—C6—C7—O2	179.7 (2)	C1—O1—C16—C8	0.2 (3)
C5—C6—C7—O2	−1.5 (3)	C1—O1—C16—C15	−179.36 (16)
C1—C6—C7—C8	0.2 (3)	C9—C8—C16—O1	179.58 (18)
C5—C6—C7—C8	179.03 (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—C16	1.0 (3)	C7—C8—C16—C15	178.25 (19)
O2—C7—C8—C9	0.7 (3)	N1—C15—C16—O1	−2.1 (3)
C6—C7—C8—C9	−179.84 (18)	C11—C15—C16—O1	177.68 (17)
C16—C8—C9—C10	2.7 (3)	N1—C15—C16—C8	178.38 (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, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1	0.82	2.07	2.852 (2)	160

Experimental details

Crystal data
Chemical formula	C₁₆H₉NO₂·CH₄O
M_r	279.28
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	8.102 (2), 8.791 (3), 10.150 (3)
α, β, γ (°)	102.172 (3), 108.760 (3), 93.532 (3)
V (Å³)	662.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.41 × 0.30 × 0.18

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3838, 2655, 1456
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.147, 1.02
No. of reflections	2655
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.15

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1	0.82	2.07	2.852 (2)	160

Acknowledgements

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

References

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