(E)-N′-[1-(4-Hydroxy­phen­yl)ethyl­idene]-2-(quinolin-8-yl­oxy)acetohydrazide methanol solvate

Tan, J.

doi:10.1107/S1600536809006461

organic compounds

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Volume 65| Part 3| March 2009| Page o651

doi:10.1107/S1600536809006461

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(E)-N′-[1-(4-Hydroxyphenyl)ethylidene]-2-(quinolin-8-yloxy)acetohydrazide methanol solvate

Jun Tan ^a ^*

^aCollege of Biological and Chemical Engineering, Jiaxing University, Jiaxing 314001, People's Republic of China
^*Correspondence e-mail: catalyst007@126.com

(Received 19 February 2009; accepted 22 February 2009; online 28 February 2009)

In the title compound, C₁₉H₁₇N₃O₃·CH₄O, the mean planes of the benzene ring and the quinoline rings make a dihedral angle of 75.5 (2)°. The acetohydrazide molecules are connected via pairs of intermolecular O—H⋯O hydrogen bonds into inversion dimers, and the methanol solvent molecule is linked to the acetohydrazide molecule via intermolecular N—H⋯O and bifurcated O—H⋯(N,O) hydrogen bonds.

Related literature

For background on the coordination chemistry of 8-hydroxyquinoline and its derivatives, see: Chen & Shi (1998 ). For related structures, see: Wen et al. (2005 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₉H₁₇N₃O₃·CH₄O
M_r = 367.40
Triclinic, $[P \overline 1]$
a = 9.552 (3) Å
b = 10.622 (2) Å
c = 10.665 (4) Å
α = 70.055 (5)°
β = 83.033 (4)°
γ = 65.845 (4)°
V = 927.9 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.20 × 0.18 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.982, T_max = 0.986
4927 measured reflections
3261 independent reflections
2430 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.143
S = 1.08
3261 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2ⁱ	0.82	1.85	2.647 (3)	165
O4—H4⋯N1	0.82	1.96	2.773 (3)	174
O4—H4⋯O1	0.82	2.60	3.036 (3)	115
N2—H2⋯O4	0.86	2.10	2.856 (3)	146
Symmetry code: (i) -x-1, -y+2, -z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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: 10.1107/S1600536809006461/hb2916sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809006461/hb2916Isup2.hkl

checkCIF report

Comment top

8-Hydroxyquinoline and its derivatives constitute well known ligands in coordination chemistry (Chen & Shi, 1998). In our search for new extractants of metal ions and biologically active materials, the title compound, (I), has been synthesized. We report here its crystal structure. All bond lengths and angles are normal (Allen et al., 1987), and are comparable to those in the related compound N'-(2-Fluorobenzylidene) -2-(quinolin-8-yloxy)-acetohydrazide methanol solvate (Wen et al., 2005). The mean planes of the benzene ring and the quinoline rings make a dihedral angle of 75.5 (2)°. In the crystal structure, the methanol molecule is linked to the C₁₉H₁₇N₃O₃ molecule via intermolecular O—H···O, N—H···O and O—H···N hydrogen bonds (Fig. 1), intermolecular O—H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2).

Related literature top

For background on the coordination chemistry of 8-hydroxyquinoline and its derivatives, see: Chen & Shi (1998). For related structures, see: Wen et al. (2005). For reference structural data, see: Allen et al. (1987).

Experimental top

2-(Quinolin-8-yloxy)acetohydrazide (2.18 g, 10 mmol), 1-(4-hydroxyphenyl)ethanone (1.36 g, 10 mmol), ethanol (40 ml) and some drops of acetic acid were added to a 100 ml flask, and refluxed for 3 h. After cooling to room temperature, the mixture was filtered. Pale yellow blocks of (I) were obtained by slow evaporation of a acetone-methanol (1:2, v/v) solution over a period of 3 d. Analysis calculated for C₂₀H₂₁N₃O₄: C 65.38, H 5.76, N 11.43%; found: C 65.76, H 5.47, N 11.67%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 of (I), with displacement ellipsoids drawn at the 30% probability level. The dashed lines indicate hydrogen bonds.
	Fig. 2. The structure of the dimers formed via hydrogen bonds, H atoms have been omitted for clarity. The dashed lines indicate hydrogen bonds.

(E)-N'-[1-(4-Hydroxyphenyl)ethylidene]-2-(quinolin-8- yloxy)acetohydrazide methanol solvate top

Crystal data top

C₁₉H₁₇N₃O₃·CH₄O	Z = 2
M_r = 367.40	F(000) = 388
Triclinic, P1	D_x = 1.315 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.552 (3) Å	Cell parameters from 1866 reflections
b = 10.622 (2) Å	θ = 2.5–26.5°
c = 10.665 (4) Å	µ = 0.09 mm⁻¹
α = 70.055 (5)°	T = 295 K
β = 83.033 (4)°	Block, light yellow
γ = 65.845 (4)°	0.20 × 0.18 × 0.15 mm
V = 927.9 (5) Å³

Data collection top

Bruker SMART CCD diffractometer	3261 independent reflections
Radiation source: fine-focus sealed tube	2430 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→8
T_min = 0.982, T_max = 0.986	k = −12→7
4927 measured 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0478P)² + 0.5262P] where P = (F_o² + 2F_c²)/3
3261 reflections	(Δ/σ)_max < 0.001
246 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₉H₁₇N₃O₃·CH₄O	γ = 65.845 (4)°
M_r = 367.40	V = 927.9 (5) Å³
Triclinic, P1	Z = 2
a = 9.552 (3) Å	Mo Kα radiation
b = 10.622 (2) Å	µ = 0.09 mm⁻¹
c = 10.665 (4) Å	T = 295 K
α = 70.055 (5)°	0.20 × 0.18 × 0.15 mm
β = 83.033 (4)°

Data collection top

Bruker SMART CCD diffractometer	3261 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2430 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.986	R_int = 0.021
4927 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 1.08	Δρ_max = 0.17 e Å⁻³
3261 reflections	Δρ_min = −0.20 e Å⁻³
246 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	0.32959 (17)	0.65533 (18)	0.12916 (16)	0.0512 (4)
O2	0.0115 (2)	0.8800 (2)	−0.09376 (17)	0.0620 (5)
O3	−0.83771 (19)	1.1439 (3)	0.2526 (2)	0.0726 (6)
H3	−0.8762	1.1285	0.1977	0.109*
O4	0.1513 (2)	0.5644 (2)	0.3745 (2)	0.0666 (5)
H4	0.2444	0.5347	0.3643	0.100*
N1	0.4677 (2)	0.4420 (2)	0.3533 (2)	0.0523 (5)
N2	0.0236 (2)	0.7950 (2)	0.1324 (2)	0.0516 (5)
H2	0.0807	0.7494	0.2034	0.062*
N3	−0.1361 (2)	0.8523 (2)	0.1406 (2)	0.0509 (5)
C1	0.5370 (3)	0.3362 (3)	0.4623 (3)	0.0624 (7)
H1	0.4761	0.3085	0.5321	0.075*
C2	0.6963 (3)	0.2631 (3)	0.4795 (3)	0.0694 (8)
H2A	0.7393	0.1882	0.5581	0.083*
C3	0.7866 (3)	0.3033 (3)	0.3797 (3)	0.0672 (8)
H3A	0.8928	0.2558	0.3895	0.081*
C4	0.7203 (3)	0.4173 (3)	0.2607 (3)	0.0528 (6)
C5	0.8077 (3)	0.4653 (3)	0.1532 (3)	0.0638 (8)
H5	0.9143	0.4225	0.1589	0.077*
C6	0.7356 (3)	0.5740 (3)	0.0418 (3)	0.0646 (8)
H6	0.7940	0.6059	−0.0282	0.078*
C7	0.5749 (3)	0.6397 (3)	0.0292 (3)	0.0540 (6)
H7	0.5283	0.7127	−0.0493	0.065*
C8	0.4869 (3)	0.5969 (3)	0.1319 (2)	0.0451 (6)
C9	0.5576 (3)	0.4842 (3)	0.2515 (2)	0.0449 (6)
C10	0.2571 (3)	0.7563 (3)	0.0056 (2)	0.0486 (6)
H10A	0.2909	0.7093	−0.0627	0.058*
H10B	0.2884	0.8376	−0.0199	0.058*
C11	0.0854 (3)	0.8127 (3)	0.0119 (2)	0.0455 (6)
C12	−0.1908 (3)	0.8900 (3)	0.2445 (2)	0.0463 (6)
C13	−0.0992 (3)	0.8864 (3)	0.3513 (3)	0.0587 (7)
H13A	−0.0081	0.7983	0.3722	0.088*
H13B	−0.1597	0.8897	0.4298	0.088*
H13C	−0.0712	0.9689	0.3203	0.088*
C14	−0.3614 (3)	0.9510 (3)	0.2510 (2)	0.0447 (6)
C15	−0.4388 (3)	1.0446 (3)	0.3227 (3)	0.0577 (7)
H15	−0.3831	1.0654	0.3729	0.069*
C16	−0.5971 (3)	1.1082 (3)	0.3218 (3)	0.0640 (8)
H16	−0.6464	1.1716	0.3705	0.077*
C17	−0.6820 (3)	1.0784 (3)	0.2495 (2)	0.0508 (6)
C18	−0.6079 (3)	0.9839 (3)	0.1787 (3)	0.0578 (7)
H18	−0.6644	0.9622	0.1300	0.069*
C19	−0.4494 (3)	0.9211 (3)	0.1796 (3)	0.0554 (7)
H19	−0.4006	0.8573	0.1313	0.067*
C20	0.0957 (4)	0.4729 (4)	0.3498 (5)	0.1075 (14)
H20A	0.1292	0.3811	0.4202	0.161*
H20B	0.1338	0.4576	0.2664	0.161*
H20C	−0.0144	0.5168	0.3456	0.161*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0323 (9)	0.0558 (10)	0.0498 (10)	−0.0091 (7)	−0.0026 (7)	−0.0074 (8)
O2	0.0498 (11)	0.0737 (13)	0.0533 (11)	−0.0199 (9)	−0.0132 (9)	−0.0100 (9)
O3	0.0358 (10)	0.0972 (16)	0.0839 (15)	−0.0128 (10)	−0.0033 (9)	−0.0429 (12)
O4	0.0499 (11)	0.0642 (12)	0.0743 (13)	−0.0161 (10)	0.0034 (10)	−0.0174 (10)
N1	0.0471 (12)	0.0523 (12)	0.0533 (12)	−0.0163 (10)	−0.0040 (10)	−0.0142 (10)
N2	0.0341 (11)	0.0552 (13)	0.0525 (13)	−0.0051 (9)	−0.0079 (9)	−0.0144 (10)
N3	0.0346 (11)	0.0521 (12)	0.0560 (13)	−0.0064 (9)	−0.0049 (9)	−0.0166 (10)
C1	0.0664 (18)	0.0619 (17)	0.0547 (16)	−0.0257 (15)	−0.0087 (13)	−0.0096 (14)
C2	0.0640 (19)	0.0627 (18)	0.0703 (19)	−0.0161 (15)	−0.0258 (16)	−0.0099 (15)
C3	0.0456 (16)	0.0624 (18)	0.085 (2)	−0.0084 (13)	−0.0224 (15)	−0.0211 (16)
C4	0.0409 (14)	0.0533 (15)	0.0679 (17)	−0.0133 (12)	−0.0092 (12)	−0.0268 (13)
C5	0.0331 (13)	0.0740 (19)	0.086 (2)	−0.0173 (13)	0.0023 (14)	−0.0330 (17)
C6	0.0447 (15)	0.0720 (19)	0.077 (2)	−0.0245 (14)	0.0125 (14)	−0.0252 (16)
C7	0.0457 (14)	0.0550 (15)	0.0571 (16)	−0.0182 (12)	0.0020 (12)	−0.0152 (12)
C8	0.0355 (12)	0.0448 (13)	0.0546 (14)	−0.0122 (10)	−0.0009 (11)	−0.0194 (11)
C9	0.0383 (13)	0.0446 (13)	0.0544 (15)	−0.0132 (11)	−0.0038 (11)	−0.0211 (11)
C10	0.0424 (13)	0.0505 (14)	0.0477 (14)	−0.0162 (11)	−0.0022 (11)	−0.0114 (11)
C11	0.0408 (13)	0.0409 (13)	0.0514 (14)	−0.0118 (10)	−0.0062 (11)	−0.0134 (11)
C12	0.0388 (13)	0.0423 (13)	0.0495 (14)	−0.0100 (10)	−0.0044 (11)	−0.0104 (11)
C13	0.0438 (14)	0.0680 (18)	0.0578 (16)	−0.0124 (13)	−0.0077 (12)	−0.0215 (14)
C14	0.0385 (12)	0.0462 (13)	0.0431 (13)	−0.0127 (10)	−0.0031 (10)	−0.0103 (11)
C15	0.0410 (14)	0.0717 (18)	0.0655 (17)	−0.0133 (13)	−0.0071 (12)	−0.0362 (15)
C16	0.0456 (15)	0.0753 (19)	0.0713 (18)	−0.0074 (13)	−0.0030 (13)	−0.0427 (16)
C17	0.0358 (13)	0.0590 (16)	0.0503 (14)	−0.0131 (11)	−0.0026 (11)	−0.0147 (12)
C18	0.0463 (15)	0.0756 (19)	0.0649 (17)	−0.0263 (14)	−0.0011 (12)	−0.0349 (15)
C19	0.0450 (15)	0.0657 (17)	0.0630 (16)	−0.0187 (13)	0.0031 (12)	−0.0341 (14)
C20	0.088 (3)	0.082 (3)	0.168 (4)	−0.045 (2)	0.025 (3)	−0.052 (3)

Geometric parameters (Å, º) top

O1—C8	1.371 (3)	C7—C8	1.364 (3)
O1—C10	1.420 (3)	C7—H7	0.9300
O2—C11	1.229 (3)	C8—C9	1.423 (3)
O3—C17	1.361 (3)	C10—C11	1.501 (3)
O3—H3	0.8200	C10—H10A	0.9700
O4—C20	1.389 (4)	C10—H10B	0.9700
O4—H4	0.8200	C12—C14	1.490 (3)
N1—C1	1.319 (3)	C12—C13	1.501 (3)
N1—C9	1.369 (3)	C13—H13A	0.9600
N2—C11	1.333 (3)	C13—H13B	0.9600
N2—N3	1.396 (3)	C13—H13C	0.9600
N2—H2	0.8600	C14—C15	1.379 (3)
N3—C12	1.286 (3)	C14—C19	1.387 (3)
C1—C2	1.399 (4)	C15—C16	1.380 (4)
C1—H1	0.9300	C15—H15	0.9300
C2—C3	1.352 (4)	C16—C17	1.372 (4)
C2—H2A	0.9300	C16—H16	0.9300
C3—C4	1.413 (4)	C17—C18	1.372 (4)
C3—H3A	0.9300	C18—C19	1.382 (4)
C4—C5	1.410 (4)	C18—H18	0.9300
C4—C9	1.420 (3)	C19—H19	0.9300
C5—C6	1.353 (4)	C20—H20A	0.9600
C5—H5	0.9300	C20—H20B	0.9600
C6—C7	1.404 (4)	C20—H20C	0.9600
C6—H6	0.9300

C8—O1—C10	116.27 (18)	C11—C10—H10B	109.1
C17—O3—H3	109.5	H10A—C10—H10B	107.9
C20—O4—H4	109.5	O2—C11—N2	124.5 (2)
C1—N1—C9	117.8 (2)	O2—C11—C10	117.8 (2)
C11—N2—N3	118.39 (19)	N2—C11—C10	117.4 (2)
C11—N2—H2	120.8	N3—C12—C14	115.1 (2)
N3—N2—H2	120.8	N3—C12—C13	125.8 (2)
C12—N3—N2	116.1 (2)	C14—C12—C13	118.9 (2)
N1—C1—C2	124.1 (3)	C12—C13—H13A	109.5
N1—C1—H1	117.9	C12—C13—H13B	109.5
C2—C1—H1	117.9	H13A—C13—H13B	109.5
C3—C2—C1	118.7 (3)	C12—C13—H13C	109.5
C3—C2—H2A	120.6	H13A—C13—H13C	109.5
C1—C2—H2A	120.6	H13B—C13—H13C	109.5
C2—C3—C4	120.3 (3)	C15—C14—C19	117.1 (2)
C2—C3—H3A	119.9	C15—C14—C12	121.7 (2)
C4—C3—H3A	119.9	C19—C14—C12	121.1 (2)
C5—C4—C3	123.2 (2)	C14—C15—C16	121.5 (2)
C5—C4—C9	119.7 (2)	C14—C15—H15	119.2
C3—C4—C9	117.1 (3)	C16—C15—H15	119.2
C6—C5—C4	119.7 (2)	C17—C16—C15	120.4 (2)
C6—C5—H5	120.2	C17—C16—H16	119.8
C4—C5—H5	120.2	C15—C16—H16	119.8
C5—C6—C7	121.7 (3)	O3—C17—C18	122.9 (2)
C5—C6—H6	119.2	O3—C17—C16	117.8 (2)
C7—C6—H6	119.2	C18—C17—C16	119.3 (2)
C8—C7—C6	120.2 (3)	C17—C18—C19	120.0 (2)
C8—C7—H7	119.9	C17—C18—H18	120.0
C6—C7—H7	119.9	C19—C18—H18	120.0
C7—C8—O1	124.3 (2)	C18—C19—C14	121.6 (2)
C7—C8—C9	120.1 (2)	C18—C19—H19	119.2
O1—C8—C9	115.5 (2)	C14—C19—H19	119.2
N1—C9—C4	122.0 (2)	O4—C20—H20A	109.5
N1—C9—C8	119.4 (2)	O4—C20—H20B	109.5
C4—C9—C8	118.6 (2)	H20A—C20—H20B	109.5
O1—C10—C11	112.4 (2)	O4—C20—H20C	109.5
O1—C10—H10A	109.1	H20A—C20—H20C	109.5
C11—C10—H10A	109.1	H20B—C20—H20C	109.5
O1—C10—H10B	109.1

C11—N2—N3—C12	−151.2 (2)	O1—C8—C9—C4	179.2 (2)
C9—N1—C1—C2	−1.0 (4)	C8—O1—C10—C11	179.3 (2)
N1—C1—C2—C3	0.9 (5)	N3—N2—C11—O2	2.2 (4)
C1—C2—C3—C4	0.0 (5)	N3—N2—C11—C10	177.3 (2)
C2—C3—C4—C5	179.6 (3)	O1—C10—C11—O2	−167.4 (2)
C2—C3—C4—C9	−0.7 (4)	O1—C10—C11—N2	17.2 (3)
C3—C4—C5—C6	179.2 (3)	N2—N3—C12—C14	179.9 (2)
C9—C4—C5—C6	−0.5 (4)	N2—N3—C12—C13	4.1 (4)
C4—C5—C6—C7	−0.8 (4)	N3—C12—C14—C15	−154.8 (3)
C5—C6—C7—C8	1.5 (4)	C13—C12—C14—C15	21.3 (4)
C6—C7—C8—O1	179.5 (2)	N3—C12—C14—C19	22.1 (3)
C6—C7—C8—C9	−0.7 (4)	C13—C12—C14—C19	−161.8 (2)
C10—O1—C8—C7	6.5 (3)	C19—C14—C15—C16	−1.2 (4)
C10—O1—C8—C9	−173.2 (2)	C12—C14—C15—C16	175.9 (3)
C1—N1—C9—C4	0.2 (4)	C14—C15—C16—C17	0.5 (5)
C1—N1—C9—C8	179.3 (2)	C15—C16—C17—O3	179.8 (3)
C5—C4—C9—N1	−179.7 (2)	C15—C16—C17—C18	0.4 (4)
C3—C4—C9—N1	0.6 (4)	O3—C17—C18—C19	180.0 (3)
C5—C4—C9—C8	1.2 (4)	C16—C17—C18—C19	−0.7 (4)
C3—C4—C9—C8	−178.5 (2)	C17—C18—C19—C14	0.0 (4)
C7—C8—C9—N1	−179.7 (2)	C15—C14—C19—C18	0.9 (4)
O1—C8—C9—N1	0.1 (3)	C12—C14—C19—C18	−176.1 (2)
C7—C8—C9—C4	−0.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.82	1.85	2.647 (3)	165
O4—H4···N1	0.82	1.96	2.773 (3)	174
O4—H4···O1	0.82	2.60	3.036 (3)	115
N2—H2···O4	0.86	2.10	2.856 (3)	146

Symmetry code: (i) −x−1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₇N₃O₃·CH₄O
M_r	367.40
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	9.552 (3), 10.622 (2), 10.665 (4)
α, β, γ (°)	70.055 (5), 83.033 (4), 65.845 (4)
V (Å³)	927.9 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.18 × 0.15

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.982, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	4927, 3261, 2430
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.143, 1.08
No. of reflections	3261
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.20

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.82	1.85	2.647 (3)	165
O4—H4···N1	0.82	1.96	2.773 (3)	174
O4—H4···O1	0.82	2.60	3.036 (3)	115
N2—H2···O4	0.86	2.10	2.856 (3)	146

Symmetry code: (i) −x−1, −y+2, −z.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Chen, C. H. & Shi, J. M. (1998). Coord. Chem. Rev. 171, 161—174. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Wen, Y.-H., Zhang, S.-S., Li, M.-J. & Li, X.-M. (2005). Acta Cryst. E61, o2045–o2046. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 3| March 2009| Page o651

doi:10.1107/S1600536809006461

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-N′-[1-(4-Hy­droxy­phen­yl)ethyl­­idene]-2-(quinolin-8-yl­­oxy)acetohydrazide methanol solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

(E)-N′-[1-(4-Hydroxyphenyl)ethylidene]-2-(quinolin-8-yloxy)acetohydrazide methanol solvate