(E)-N'-(2,5-Dimethoxy-benzyl-idene)-2-(8-quinol-yloxy)acetohydrazide methanol solvate.

The two mol-ecules in the asymmetric unit of the title compound, C(20)H(19)N(3)O(4)·CH(4)O, are paired via O-H⋯(O,N), N-H⋯O, and C-H⋯O hydrogen bonds. The mol-ecular skeleton of the acetohydrazide mol-ecule is close to planar; the benzene and quinoline mean planes form a dihedral angle of 3.9 (3)°. The crystal packing exhibits weak inter-molecular C-H⋯O hydrogen bonds and π-π inter-actions, indicated by short distances of 3.668 (3) Å, between the centroids of N-containing six-membered rings from neighbouring acetohydrazide mol-ecules.

Related literature

For applications of 8-hydroxy­quinoline and its derivatives, see: Park et al. (2006 ▶); Karmakar et al. (2007 ▶). For a related structure, see Wen et al. (2005 ▶).

Experimental

Crystal data

C20H19N3O4·CH4O

M = 397.42

Triclinic,

a = 9.4199 (12) Å

b = 10.8652 (14) Å

c = 11.1721 (14) Å

α = 93.268 (1)°

β = 112.816 (2)°

γ = 107.859 (3)°

V = 982.8 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.22 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.979, T max = 0.985

5196 measured reflections

3456 independent reflections

2363 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.149

S = 1.03

3456 reflections

263 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.33 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/S1600536809015165/cv2552sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015165/cv2552Isup2.hkl

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

C20H19N3O4·CH4O	Z = 2
Mr = 397.42	F(000) = 420
Triclinic, P1	Dx = 1.343 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4199 (12) Å	Cell parameters from 1903 reflections
b = 10.8652 (14) Å	θ = 2.5–26.9°
c = 11.1721 (14) Å	µ = 0.10 mm−1
α = 93.268 (1)°	T = 295 K
β = 112.816 (2)°	Block, colorless
γ = 107.859 (3)°	0.22 × 0.18 × 0.16 mm
V = 982.8 (2) Å3

Bruker SMART CCD area-detector diffractometer	3456 independent reflections
Radiation source: fine-focus sealed tube	2363 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
Tmin = 0.979, Tmax = 0.985	k = −12→12
5196 measured reflections	l = −13→10

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) = 0.149	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0685P)2 + 0.304P] where P = (Fo2 + 2Fc2)/3
3456 reflections	(Δ/σ)max < 0.001
263 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.33 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	−0.24162 (17)	0.13371 (15)	0.32912 (13)	0.0535 (4)
O2	0.0642 (2)	0.1461 (2)	0.64429 (16)	0.0858 (6)
O3	0.4628 (2)	0.39500 (19)	0.28395 (18)	0.0788 (5)
O4	0.8736 (2)	0.3699 (2)	0.7849 (2)	0.0949 (7)
O5	−0.0293 (3)	0.2135 (3)	0.1843 (2)	0.1266 (11)
H5A	−0.1081	0.2324	0.1818	0.190*
N1	−0.3582 (2)	0.19146 (18)	0.08689 (17)	0.0528 (5)
N2	0.0876 (2)	0.19807 (18)	0.45814 (17)	0.0560 (5)
H2	0.0371	0.2020	0.3766	0.067*
N3	0.2580 (2)	0.23818 (18)	0.51768 (18)	0.0558 (5)
C1	−0.4175 (3)	0.2184 (2)	−0.0328 (2)	0.0601 (6)
H1	−0.3428	0.2594	−0.0664	0.072*
C2	−0.5851 (3)	0.1892 (2)	−0.1121 (2)	0.0643 (7)
H2A	−0.6203	0.2104	−0.1956	0.077*
C3	−0.6951 (3)	0.1293 (2)	−0.0644 (2)	0.0627 (6)
H3	−0.8073	0.1086	−0.1154	0.075*
C4	−0.6394 (3)	0.0981 (2)	0.0630 (2)	0.0536 (6)
C5	−0.7479 (3)	0.0345 (3)	0.1181 (3)	0.0662 (7)
H5	−0.8608	0.0141	0.0709	0.079*
C6	−0.6890 (3)	0.0033 (3)	0.2383 (3)	0.0693 (7)
H6	−0.7616	−0.0393	0.2731	0.083*
C7	−0.5183 (3)	0.0346 (2)	0.3117 (2)	0.0575 (6)
H7	−0.4796	0.0116	0.3941	0.069*
C8	−0.4090 (2)	0.0981 (2)	0.2636 (2)	0.0474 (5)
C9	−0.4680 (3)	0.1308 (2)	0.1355 (2)	0.0473 (5)
C10	−0.1828 (3)	0.1048 (2)	0.4579 (2)	0.0543 (6)
H10A	−0.2262	0.0101	0.4509	0.065*
H10B	−0.2240	0.1450	0.5106	0.065*
C11	0.0023 (3)	0.1532 (2)	0.5280 (2)	0.0549 (6)
C12	0.3277 (3)	0.2839 (2)	0.4443 (2)	0.0603 (6)
H12	0.2622	0.2859	0.3576	0.072*
C13	0.5061 (3)	0.3334 (2)	0.4906 (2)	0.0568 (6)
C14	0.5723 (3)	0.3921 (2)	0.4061 (3)	0.0625 (6)
C15	0.7399 (4)	0.4419 (3)	0.4488 (3)	0.0800 (8)
H15	0.7843	0.4798	0.3926	0.096*
C16	0.8436 (4)	0.4366 (3)	0.5739 (3)	0.0842 (9)
H16	0.9572	0.4722	0.6020	0.101*
C17	0.7807 (3)	0.3791 (3)	0.6577 (3)	0.0701 (7)
C18	0.6115 (3)	0.3272 (2)	0.6158 (3)	0.0637 (6)
H18	0.5682	0.2879	0.6720	0.076*
C19	0.5240 (4)	0.4653 (3)	0.2014 (3)	0.0892 (9)
H19A	0.5871	0.5557	0.2460	0.134*
H19B	0.4335	0.4616	0.1206	0.134*
H19C	0.5931	0.4265	0.1814	0.134*
C20	1.0484 (4)	0.4126 (4)	0.8254 (4)	0.1123 (12)
H20A	1.0716	0.3572	0.7710	0.168*
H20B	1.1020	0.4068	0.9164	0.168*
H20C	1.0885	0.5023	0.8159	0.168*
C21	0.0330 (4)	0.2797 (4)	0.1045 (3)	0.0957 (10)
H21A	0.0494	0.3715	0.1245	0.144*
H21B	−0.0432	0.2434	0.0133	0.144*
H21C	0.1365	0.2705	0.1197	0.144*

	U11	U22	U33	U12	U13	U23
O1	0.0409 (8)	0.0744 (10)	0.0410 (8)	0.0212 (7)	0.0117 (7)	0.0201 (7)
O2	0.0538 (10)	0.1467 (18)	0.0475 (10)	0.0343 (11)	0.0108 (8)	0.0388 (11)
O3	0.0767 (12)	0.0900 (13)	0.0686 (12)	0.0228 (10)	0.0340 (10)	0.0253 (10)
O4	0.0494 (11)	0.1275 (18)	0.0953 (15)	0.0243 (11)	0.0215 (10)	0.0391 (13)
O5	0.0554 (12)	0.231 (3)	0.0757 (14)	0.0286 (15)	0.0217 (11)	0.0755 (17)
N1	0.0500 (11)	0.0604 (11)	0.0436 (10)	0.0208 (9)	0.0143 (9)	0.0138 (9)
N2	0.0412 (10)	0.0703 (12)	0.0432 (10)	0.0135 (9)	0.0089 (8)	0.0160 (9)
N3	0.0412 (10)	0.0607 (12)	0.0548 (11)	0.0126 (9)	0.0139 (9)	0.0118 (9)
C1	0.0621 (15)	0.0668 (15)	0.0468 (13)	0.0245 (12)	0.0164 (12)	0.0188 (11)
C2	0.0704 (17)	0.0686 (16)	0.0465 (13)	0.0317 (13)	0.0112 (12)	0.0177 (11)
C3	0.0519 (14)	0.0673 (15)	0.0549 (14)	0.0260 (12)	0.0052 (12)	0.0122 (12)
C4	0.0458 (12)	0.0561 (13)	0.0493 (12)	0.0219 (10)	0.0083 (10)	0.0069 (10)
C5	0.0405 (13)	0.0817 (17)	0.0658 (16)	0.0215 (12)	0.0121 (12)	0.0161 (13)
C6	0.0475 (14)	0.0895 (19)	0.0670 (16)	0.0188 (13)	0.0245 (12)	0.0199 (14)
C7	0.0506 (13)	0.0723 (16)	0.0487 (13)	0.0231 (12)	0.0186 (11)	0.0167 (11)
C8	0.0396 (12)	0.0538 (12)	0.0434 (11)	0.0181 (10)	0.0115 (10)	0.0068 (9)
C9	0.0452 (12)	0.0485 (12)	0.0431 (11)	0.0191 (10)	0.0124 (10)	0.0071 (9)
C10	0.0471 (13)	0.0720 (15)	0.0431 (12)	0.0235 (11)	0.0154 (10)	0.0214 (11)
C11	0.0467 (13)	0.0679 (15)	0.0437 (12)	0.0211 (11)	0.0117 (10)	0.0174 (11)
C12	0.0515 (14)	0.0667 (15)	0.0543 (14)	0.0162 (11)	0.0181 (12)	0.0106 (11)
C13	0.0510 (14)	0.0536 (13)	0.0624 (15)	0.0152 (11)	0.0240 (12)	0.0073 (11)
C14	0.0608 (15)	0.0559 (14)	0.0722 (16)	0.0179 (12)	0.0324 (13)	0.0094 (12)
C15	0.0690 (18)	0.088 (2)	0.094 (2)	0.0265 (15)	0.0457 (17)	0.0337 (17)
C16	0.0548 (16)	0.093 (2)	0.108 (2)	0.0191 (15)	0.0427 (17)	0.0303 (18)
C17	0.0496 (15)	0.0756 (17)	0.0789 (18)	0.0232 (13)	0.0203 (14)	0.0169 (14)
C18	0.0540 (15)	0.0660 (15)	0.0709 (16)	0.0177 (12)	0.0292 (13)	0.0139 (12)
C19	0.102 (2)	0.088 (2)	0.0793 (19)	0.0258 (18)	0.0458 (18)	0.0277 (16)
C20	0.0522 (18)	0.155 (3)	0.114 (3)	0.033 (2)	0.0210 (18)	0.041 (2)
C21	0.076 (2)	0.121 (3)	0.082 (2)	0.0229 (18)	0.0332 (17)	0.0275 (19)

O1—C8	1.367 (2)	C7—C8	1.364 (3)
O1—C10	1.420 (2)	C7—H7	0.9300
O2—C11	1.219 (3)	C8—C9	1.430 (3)
O3—C14	1.364 (3)	C10—C11	1.504 (3)
O3—C19	1.410 (3)	C10—H10A	0.9700
O4—C17	1.378 (3)	C10—H10B	0.9700
O4—C20	1.435 (3)	C12—C13	1.456 (3)
O5—C21	1.371 (3)	C12—H12	0.9300
O5—H5A	0.8200	C13—C18	1.386 (3)
N1—C1	1.324 (3)	C13—C14	1.403 (3)
N1—C9	1.363 (3)	C14—C15	1.369 (4)
N2—C11	1.335 (3)	C15—C16	1.378 (4)
N2—N3	1.385 (2)	C15—H15	0.9300
N2—H2	0.8600	C16—C17	1.374 (4)
N3—C12	1.271 (3)	C16—H16	0.9300
C1—C2	1.398 (3)	C17—C18	1.385 (3)
C1—H1	0.9300	C18—H18	0.9300
C2—C3	1.355 (4)	C19—H19A	0.9600
C2—H2A	0.9300	C19—H19B	0.9600
C3—C4	1.414 (3)	C19—H19C	0.9600
C3—H3	0.9300	C20—H20A	0.9600
C4—C9	1.411 (3)	C20—H20B	0.9600
C4—C5	1.415 (3)	C20—H20C	0.9600
C5—C6	1.348 (3)	C21—H21A	0.9600
C5—H5	0.9300	C21—H21B	0.9600
C6—C7	1.408 (3)	C21—H21C	0.9600
C6—H6	0.9300
C8—O1—C10	115.50 (17)	O2—C11—N2	124.4 (2)
C14—O3—C19	118.6 (2)	O2—C11—C10	117.6 (2)
C17—O4—C20	116.1 (2)	N2—C11—C10	117.96 (18)
C21—O5—H5A	109.5	N3—C12—C13	122.5 (2)
C1—N1—C9	117.75 (19)	N3—C12—H12	118.7
C11—N2—N3	119.67 (17)	C13—C12—H12	118.7
C11—N2—H2	120.2	C18—C13—C14	119.4 (2)
N3—N2—H2	120.2	C18—C13—C12	122.2 (2)
C12—N3—N2	114.67 (19)	C14—C13—C12	118.4 (2)
N1—C1—C2	124.2 (2)	O3—C14—C15	123.8 (2)
N1—C1—H1	117.9	O3—C14—C13	116.8 (2)
C2—C1—H1	117.9	C15—C14—C13	119.3 (3)
C3—C2—C1	118.4 (2)	C14—C15—C16	120.8 (3)
C3—C2—H2A	120.8	C14—C15—H15	119.6
C1—C2—H2A	120.8	C16—C15—H15	119.6
C2—C3—C4	120.1 (2)	C17—C16—C15	120.6 (3)
C2—C3—H3	120.0	C17—C16—H16	119.7
C4—C3—H3	120.0	C15—C16—H16	119.7
C9—C4—C3	117.5 (2)	C16—C17—O4	125.0 (2)
C9—C4—C5	119.7 (2)	C16—C17—C18	119.4 (3)
C3—C4—C5	122.8 (2)	O4—C17—C18	115.5 (2)
C6—C5—C4	120.5 (2)	C17—C18—C13	120.4 (2)
C6—C5—H5	119.7	C17—C18—H18	119.8
C4—C5—H5	119.7	C13—C18—H18	119.8
C5—C6—C7	120.5 (2)	O3—C19—H19A	109.5
C5—C6—H6	119.8	O3—C19—H19B	109.5
C7—C6—H6	119.8	H19A—C19—H19B	109.5
C8—C7—C6	121.0 (2)	O3—C19—H19C	109.5
C8—C7—H7	119.5	H19A—C19—H19C	109.5
C6—C7—H7	119.5	H19B—C19—H19C	109.5
C7—C8—O1	124.68 (19)	O4—C20—H20A	109.5
C7—C8—C9	119.8 (2)	O4—C20—H20B	109.5
O1—C8—C9	115.50 (18)	H20A—C20—H20B	109.5
N1—C9—C4	122.07 (19)	O4—C20—H20C	109.5
N1—C9—C8	119.45 (18)	H20A—C20—H20C	109.5
C4—C9—C8	118.5 (2)	H20B—C20—H20C	109.5
O1—C10—C11	113.06 (18)	O5—C21—H21A	109.5
O1—C10—H10A	109.0	O5—C21—H21B	109.5
C11—C10—H10A	109.0	H21A—C21—H21B	109.5
O1—C10—H10B	109.0	O5—C21—H21C	109.5
C11—C10—H10B	109.0	H21A—C21—H21C	109.5
H10A—C10—H10B	107.8	H21B—C21—H21C	109.5
C11—N2—N3—C12	−177.4 (2)	N3—N2—C11—O2	1.0 (4)
C9—N1—C1—C2	0.3 (3)	N3—N2—C11—C10	−177.22 (19)
N1—C1—C2—C3	−0.1 (4)	O1—C10—C11—O2	172.0 (2)
C1—C2—C3—C4	0.2 (4)	O1—C10—C11—N2	−9.6 (3)
C2—C3—C4—C9	−0.6 (3)	N2—N3—C12—C13	178.7 (2)
C2—C3—C4—C5	−179.4 (2)	N3—C12—C13—C18	3.6 (4)
C9—C4—C5—C6	−0.9 (4)	N3—C12—C13—C14	−174.8 (2)
C3—C4—C5—C6	177.9 (2)	C19—O3—C14—C15	−7.1 (4)
C4—C5—C6—C7	0.6 (4)	C19—O3—C14—C13	173.3 (2)
C5—C6—C7—C8	0.7 (4)	C18—C13—C14—O3	179.8 (2)
C6—C7—C8—O1	179.0 (2)	C12—C13—C14—O3	−1.8 (3)
C6—C7—C8—C9	−1.6 (3)	C18—C13—C14—C15	0.2 (4)
C10—O1—C8—C7	−2.3 (3)	C12—C13—C14—C15	178.6 (2)
C10—O1—C8—C9	178.19 (18)	O3—C14—C15—C16	179.5 (3)
C1—N1—C9—C4	−0.7 (3)	C13—C14—C15—C16	−0.9 (4)
C1—N1—C9—C8	179.0 (2)	C14—C15—C16—C17	1.1 (5)
C3—C4—C9—N1	0.8 (3)	C15—C16—C17—O4	−179.3 (3)
C5—C4—C9—N1	179.7 (2)	C15—C16—C17—C18	−0.5 (4)
C3—C4—C9—C8	−178.88 (19)	C20—O4—C17—C16	−6.5 (4)
C5—C4—C9—C8	0.0 (3)	C20—O4—C17—C18	174.7 (3)
C7—C8—C9—N1	−178.5 (2)	C16—C17—C18—C13	−0.2 (4)
O1—C8—C9—N1	1.0 (3)	O4—C17—C18—C13	178.7 (2)
C7—C8—C9—C4	1.2 (3)	C14—C13—C18—C17	0.4 (4)
O1—C8—C9—C4	−179.29 (18)	C12—C13—C18—C17	−178.0 (2)
C8—O1—C10—C11	−176.68 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O1	0.82	2.53	2.996 (3)	117
O5—H5A···N1	0.82	2.06	2.782 (3)	147
N2—H2···O5	0.86	2.01	2.856 (3)	166
C12—H12···O5	0.93	2.51	3.305 (3)	144
C3—H3···O2i	0.93	2.60	3.220 (3)	125
C20—H20A···O2ii	0.96	2.59	3.511 (5)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O1	0.82	2.53	2.996 (3)	117
O5—H5A⋯N1	0.82	2.06	2.782 (3)	147
N2—H2⋯O5	0.86	2.01	2.856 (3)	166
C12—H12⋯O5	0.93	2.51	3.305 (3)	144
C3—H3⋯O2i	0.93	2.60	3.220 (3)	125
C20—H20A⋯O2ii	0.96	2.59	3.511 (5)	160

Symmetry codes: (i) ; (ii) .