(E)-N'-[1-(4-Hydroxy-phen-yl)ethyl-idene]-2-(quinolin-8-yl-oxy)acetohydrazide methanol solvate.

In the title compound, C(19)H(17)N(3)O(3)·CH(4)O, the mean planes of the benzene ring and the quinoline rings make a dihedral angle of 75.5 (2)°. The acetohydrazide mol-ecules are connected via pairs of inter-molecular O-H⋯O hydrogen bonds into inversion dimers, and the methanol solvent mol-ecule is linked to the acetohydrazide mol-ecule via inter-molecular 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 = 367.40

Triclinic,

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[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.143

S = 1.08

3261 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.20 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006461/hb2916sup1.cif

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

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

C19H17N3O3·CH4O	Z = 2
Mr = 367.40	F(000) = 388
Triclinic, P1	Dx = 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

Bruker SMART CCD diffractometer	3261 independent reflections
Radiation source: fine-focus sealed tube	2430 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→8
Tmin = 0.982, Tmax = 0.986	k = −12→7
4927 measured reflections	l = −12→12

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(Fo2) + (0.0478P)2 + 0.5262P] where P = (Fo2 + 2Fc2)/3
3261 reflections	(Δ/σ)max < 0.001
246 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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	0.32959 (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*

	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)

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)

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

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) .