(E)-N'-(3,4-Dimethoxy-benzyl-idene)-2-(8-quinol-yloxy)acetohydrazide-methanol-water (1/1/1).

In the title compound, C(20)H(19)N(3)O(4)·CH(4)O·H(2)O, the Schiff base mol-ecule is almost planar, with a dihedral angle of 1.2 (1)° between the benzene ring and the quinoline ring system. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring. In the crystal, the methanol and water solvent mol-ecules are linked to the Schiff base mol-ecule via N-H⋯O, O-H⋯O, O-H⋯N and O-H⋯(O,N) hydrogen bonds.

Related literature

For background to the applications of 8-hydroxy­quinoline and its derivatives, see: Bratzel et al. (1972 ▶); Karmakar et al. (2007 ▶); Pierre et al. (2003 ▶). For a Schiff base compound containing 2,5-dimethoxy­benzaldehyde, see: Wang et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C20H19N3O4·CH4O·H2O

M = 415.44

Triclinic,

a = 8.807 (2) Å

b = 10.071 (3) Å

c = 13.121 (3) Å

α = 68.702 (4)°

β = 74.552 (3)°

γ = 82.458 (5)°

V = 1044.4 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.21 × 0.18 × 0.16 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.980, T max = 0.985

5612 measured reflections

3676 independent reflections

1571 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.126

S = 1.01

3676 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.17 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/S1600536809051034/hb5253sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051034/hb5253Isup2.hkl

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

C20H19N3O4·CH4O·H2O	Z = 2
Mr = 415.44	F(000) = 440
Triclinic, P1	Dx = 1.321 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.807 (2) Å	Cell parameters from 583 reflections
b = 10.071 (3) Å	θ = 2.6–22.5°
c = 13.121 (3) Å	µ = 0.10 mm−1
α = 68.702 (4)°	T = 295 K
β = 74.552 (3)°	Block, colourless
γ = 82.458 (5)°	0.21 × 0.18 × 0.16 mm
V = 1044.4 (4) Å3

Siemens SMART CCD diffractometer	3676 independent reflections
Radiation source: fine-focus sealed tube	1571 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 25.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.980, Tmax = 0.985	k = −10→11
5612 measured reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052	H-atom parameters constrained
wR(F2) = 0.126	w = 1/[σ2(Fo2) + (0.0363P)2 + 0.0145P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
3676 reflections	Δρmax = 0.19 e Å−3
273 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0063 (11)

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	0.9264 (2)	0.2984 (2)	1.08007 (16)	0.0553 (6)
O2	0.7983 (3)	0.3641 (2)	0.83136 (18)	0.0739 (7)
O3	0.3497 (2)	0.9140 (2)	0.60039 (16)	0.0594 (6)
O4	0.2433 (3)	1.1261 (2)	0.66550 (17)	0.0672 (7)
O5	0.7438 (3)	0.5521 (2)	0.15037 (15)	0.0700 (7)
H21	0.7970	0.4803	0.1834	0.105*
H22	0.6479	0.5351	0.1841	0.105*
O6	0.5689 (3)	0.4737 (3)	0.7121 (2)	0.0931 (9)
H6	0.6306	0.4628	0.7519	0.140*
N1	0.9468 (3)	0.3418 (3)	1.2638 (2)	0.0573 (8)
N2	0.7469 (3)	0.4881 (3)	0.95154 (19)	0.0507 (7)
H8	0.7600	0.4950	1.0121	0.061*
N3	0.6533 (3)	0.5866 (3)	0.88784 (19)	0.0517 (7)
C1	0.9595 (4)	0.3630 (4)	1.3543 (3)	0.0787 (12)
H1	0.9108	0.4449	1.3675	0.094*
C2	1.0419 (5)	0.2701 (4)	1.4323 (3)	0.0831 (12)
H2	1.0470	0.2908	1.4948	0.100*
C3	1.1133 (4)	0.1508 (4)	1.4153 (3)	0.0739 (11)
H3	1.1686	0.0883	1.4660	0.089*
C4	1.1039 (4)	0.1214 (4)	1.3206 (3)	0.0542 (9)
C5	1.1758 (4)	−0.0007 (4)	1.2967 (3)	0.0676 (10)
H5	1.2304	−0.0675	1.3459	0.081*
C6	1.1660 (4)	−0.0212 (4)	1.2027 (3)	0.0737 (11)
H6A	1.2138	−0.1023	1.1878	0.088*
C7	1.0845 (4)	0.0785 (4)	1.1268 (3)	0.0627 (10)
H7	1.0804	0.0636	1.0617	0.075*
C8	1.0114 (4)	0.1970 (3)	1.1484 (3)	0.0506 (8)
C9	1.0192 (3)	0.2217 (3)	1.2462 (2)	0.0487 (8)
C10	0.9210 (4)	0.2751 (3)	0.9812 (2)	0.0556 (9)
H10A	0.8837	0.1802	1.0017	0.067*
H10B	1.0269	0.2788	0.9338	0.067*
C11	0.8163 (4)	0.3817 (4)	0.9153 (3)	0.0541 (9)
C12	0.5916 (4)	0.6888 (3)	0.9221 (2)	0.0531 (9)
H12	0.6081	0.6919	0.9883	0.064*
C13	0.4960 (4)	0.8004 (3)	0.8595 (2)	0.0481 (8)
C14	0.4684 (3)	0.7989 (3)	0.7596 (2)	0.0469 (8)
H14	0.5083	0.7229	0.7348	0.056*
C15	0.3838 (4)	0.9073 (3)	0.6981 (2)	0.0486 (8)
C16	0.3235 (4)	1.0225 (3)	0.7344 (3)	0.0520 (9)
C17	0.3500 (4)	1.0262 (3)	0.8314 (3)	0.0613 (10)
H17	0.3111	1.1031	0.8553	0.074*
C18	0.4354 (4)	0.9145 (4)	0.8945 (3)	0.0590 (9)
H18	0.4517	0.9170	0.9610	0.071*
C19	0.4215 (4)	0.8044 (3)	0.5551 (2)	0.0688 (11)
H19A	0.5339	0.8039	0.5433	0.103*
H19B	0.3950	0.8226	0.4847	0.103*
H19C	0.3836	0.7134	0.6071	0.103*
C20	0.1775 (5)	1.2441 (4)	0.6990 (3)	0.0983 (14)
H20A	0.0973	1.2123	0.7675	0.147*
H20B	0.1319	1.3124	0.6411	0.147*
H20C	0.2586	1.2877	0.7111	0.147*
C21	0.6316 (5)	0.4092 (5)	0.6337 (3)	0.1262 (19)
H21A	0.7383	0.4372	0.5979	0.189*
H21B	0.5703	0.4378	0.5781	0.189*
H21C	0.6301	0.3076	0.6700	0.189*

	U11	U22	U33	U12	U13	U23
O1	0.0614 (15)	0.0611 (15)	0.0474 (12)	0.0089 (12)	−0.0221 (12)	−0.0206 (11)
O2	0.092 (2)	0.0846 (18)	0.0659 (15)	0.0131 (14)	−0.0410 (14)	−0.0398 (14)
O3	0.0733 (17)	0.0556 (14)	0.0531 (14)	0.0098 (12)	−0.0224 (12)	−0.0219 (11)
O4	0.0853 (18)	0.0579 (15)	0.0612 (14)	0.0245 (13)	−0.0244 (13)	−0.0280 (12)
O5	0.0792 (17)	0.0696 (16)	0.0639 (14)	0.0069 (13)	−0.0289 (13)	−0.0207 (12)
O6	0.089 (2)	0.124 (2)	0.095 (2)	0.0277 (17)	−0.0455 (16)	−0.0652 (18)
N1	0.065 (2)	0.0573 (19)	0.0494 (17)	0.0004 (15)	−0.0156 (15)	−0.0175 (14)
N2	0.0532 (18)	0.0560 (18)	0.0441 (15)	0.0010 (15)	−0.0155 (14)	−0.0167 (14)
N3	0.0538 (18)	0.0518 (17)	0.0472 (16)	−0.0010 (15)	−0.0170 (14)	−0.0110 (14)
C1	0.100 (3)	0.078 (3)	0.067 (2)	0.013 (2)	−0.032 (2)	−0.032 (2)
C2	0.109 (3)	0.093 (3)	0.056 (2)	0.006 (3)	−0.041 (2)	−0.024 (2)
C3	0.072 (3)	0.075 (3)	0.069 (3)	−0.006 (2)	−0.032 (2)	−0.008 (2)
C4	0.048 (2)	0.061 (2)	0.048 (2)	−0.0069 (19)	−0.0186 (18)	−0.0063 (18)
C5	0.057 (2)	0.062 (3)	0.078 (3)	0.007 (2)	−0.028 (2)	−0.011 (2)
C6	0.076 (3)	0.064 (3)	0.087 (3)	0.018 (2)	−0.032 (2)	−0.032 (2)
C7	0.062 (2)	0.062 (2)	0.066 (2)	0.007 (2)	−0.022 (2)	−0.023 (2)
C8	0.043 (2)	0.058 (2)	0.049 (2)	−0.0002 (18)	−0.0127 (17)	−0.0151 (18)
C9	0.039 (2)	0.052 (2)	0.049 (2)	−0.0065 (17)	−0.0088 (17)	−0.0100 (17)
C10	0.057 (2)	0.059 (2)	0.057 (2)	0.0000 (18)	−0.0172 (18)	−0.0246 (17)
C11	0.055 (2)	0.058 (2)	0.050 (2)	−0.0028 (19)	−0.0158 (18)	−0.0168 (18)
C12	0.056 (2)	0.056 (2)	0.047 (2)	−0.0072 (19)	−0.0125 (18)	−0.0154 (18)
C13	0.050 (2)	0.048 (2)	0.0437 (19)	−0.0044 (17)	−0.0084 (17)	−0.0136 (16)
C14	0.051 (2)	0.045 (2)	0.0432 (19)	−0.0037 (17)	−0.0080 (17)	−0.0161 (16)
C15	0.050 (2)	0.053 (2)	0.0426 (19)	−0.0046 (17)	−0.0089 (17)	−0.0161 (17)
C16	0.053 (2)	0.052 (2)	0.046 (2)	0.0033 (18)	−0.0085 (17)	−0.0154 (17)
C17	0.068 (3)	0.058 (2)	0.059 (2)	0.006 (2)	−0.013 (2)	−0.0263 (19)
C18	0.069 (3)	0.065 (2)	0.049 (2)	−0.002 (2)	−0.0169 (19)	−0.0246 (19)
C19	0.091 (3)	0.067 (2)	0.061 (2)	0.014 (2)	−0.028 (2)	−0.036 (2)
C20	0.145 (4)	0.072 (3)	0.105 (3)	0.045 (3)	−0.066 (3)	−0.053 (2)
C21	0.136 (4)	0.169 (5)	0.117 (4)	0.050 (4)	−0.056 (3)	−0.100 (4)

O1—C8	1.378 (3)	C6—H6A	0.9300
O1—C10	1.413 (3)	C7—C8	1.366 (4)
O2—C11	1.230 (3)	C7—H7	0.9300
O3—C15	1.369 (3)	C8—C9	1.413 (4)
O3—C19	1.437 (3)	C10—C11	1.497 (4)
O4—C16	1.366 (3)	C10—H10A	0.9700
O4—C20	1.416 (3)	C10—H10B	0.9700
O5—H21	0.8500	C12—C13	1.448 (4)
O5—H22	0.8499	C12—H12	0.9300
O6—C21	1.369 (4)	C13—C18	1.382 (4)
O6—H6	0.8200	C13—C14	1.401 (4)
N1—C1	1.315 (4)	C14—C15	1.366 (4)
N1—C9	1.359 (3)	C14—H14	0.9300
N2—C11	1.339 (3)	C15—C16	1.400 (4)
N2—N3	1.383 (3)	C16—C17	1.368 (4)
N2—H8	0.8600	C17—C18	1.397 (4)
N3—C12	1.271 (3)	C17—H17	0.9300
C1—C2	1.403 (5)	C18—H18	0.9300
C1—H1	0.9300	C19—H19A	0.9600
C2—C3	1.346 (4)	C19—H19B	0.9600
C2—H2	0.9300	C19—H19C	0.9600
C3—C4	1.403 (4)	C20—H20A	0.9600
C3—H3	0.9300	C20—H20B	0.9600
C4—C5	1.408 (4)	C20—H20C	0.9600
C4—C9	1.415 (4)	C21—H21A	0.9600
C5—C6	1.347 (4)	C21—H21B	0.9600
C5—H5	0.9300	C21—H21C	0.9600
C6—C7	1.407 (4)
C8—O1—C10	115.6 (2)	O2—C11—N2	124.2 (3)
C15—O3—C19	116.5 (2)	O2—C11—C10	117.2 (3)
C16—O4—C20	117.6 (2)	N2—C11—C10	118.7 (3)
H21—O5—H22	105.8	N3—C12—C13	120.9 (3)
C21—O6—H6	109.5	N3—C12—H12	119.5
C1—N1—C9	116.9 (3)	C13—C12—H12	119.5
C11—N2—N3	117.4 (3)	C18—C13—C14	118.3 (3)
C11—N2—H8	121.3	C18—C13—C12	120.5 (3)
N3—N2—H8	121.3	C14—C13—C12	121.1 (3)
C12—N3—N2	116.4 (3)	C15—C14—C13	121.0 (3)
N1—C1—C2	124.2 (3)	C15—C14—H14	119.5
N1—C1—H1	117.9	C13—C14—H14	119.5
C2—C1—H1	117.9	C14—C15—O3	125.0 (3)
C3—C2—C1	119.1 (3)	C14—C15—C16	120.1 (3)
C3—C2—H2	120.4	O3—C15—C16	114.9 (3)
C1—C2—H2	120.4	O4—C16—C17	125.0 (3)
C2—C3—C4	119.6 (3)	O4—C16—C15	115.2 (3)
C2—C3—H3	120.2	C17—C16—C15	119.8 (3)
C4—C3—H3	120.2	C16—C17—C18	120.0 (3)
C3—C4—C5	123.1 (3)	C16—C17—H17	120.0
C3—C4—C9	117.3 (3)	C18—C17—H17	120.0
C5—C4—C9	119.6 (3)	C13—C18—C17	120.8 (3)
C6—C5—C4	120.3 (3)	C13—C18—H18	119.6
C6—C5—H5	119.9	C17—C18—H18	119.6
C4—C5—H5	119.9	O3—C19—H19A	109.5
C5—C6—C7	120.9 (3)	O3—C19—H19B	109.5
C5—C6—H6A	119.5	H19A—C19—H19B	109.5
C7—C6—H6A	119.5	O3—C19—H19C	109.5
C8—C7—C6	120.3 (3)	H19A—C19—H19C	109.5
C8—C7—H7	119.9	H19B—C19—H19C	109.5
C6—C7—H7	119.9	O4—C20—H20A	109.5
C7—C8—O1	124.2 (3)	O4—C20—H20B	109.5
C7—C8—C9	120.2 (3)	H20A—C20—H20B	109.5
O1—C8—C9	115.6 (3)	O4—C20—H20C	109.5
N1—C9—C8	118.5 (3)	H20A—C20—H20C	109.5
N1—C9—C4	122.9 (3)	H20B—C20—H20C	109.5
C8—C9—C4	118.6 (3)	O6—C21—H21A	109.5
O1—C10—C11	113.2 (3)	O6—C21—H21B	109.5
O1—C10—H10A	108.9	H21A—C21—H21B	109.5
C11—C10—H10A	108.9	O6—C21—H21C	109.5
O1—C10—H10B	108.9	H21A—C21—H21C	109.5
C11—C10—H10B	108.9	H21B—C21—H21C	109.5
H10A—C10—H10B	107.8

D—H···A	D—H	H···A	D···A	D—H···A
N2—H8···O1	0.86	2.35	2.698 (3)	105
N2—H8···O5i	0.86	2.06	2.899 (3)	165
O6—H6···O2	0.82	1.98	2.756 (4)	156
O6—H6···N3	0.82	2.58	3.194 (4)	133
O5—H21···N1ii	0.85	2.00	2.834 (4)	168
O5—H22···O6iii	0.85	2.02	2.847 (4)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H8⋯O1	0.86	2.35	2.698 (3)	105
N2—H8⋯O5i	0.86	2.06	2.899 (3)	165
O6—H6⋯O2	0.82	1.98	2.756 (4)	156
O6—H6⋯N3	0.82	2.58	3.194 (4)	133
O5—H21⋯N1ii	0.85	2.00	2.834 (4)	168
O5—H22⋯O6iii	0.85	2.02	2.847 (4)	164

Symmetry codes: (i) ; (ii) ; (iii) .