(E)-N′-(3,4-Dimethoxy­benzyl­idene)-2-(8-quinol­yloxy)acetohydrazide–methanol–water (1/1/1)

Ma, Z.-L.

doi:10.1107/S1600536809051034

organic compounds

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Volume 65| Part 12| December 2009| Page o3230

doi:10.1107/S1600536809051034

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(E)-N′-(3,4-Dimethoxybenzylidene)-2-(8-quinolyloxy)acetohydrazide–methanol–water (1/1/1)

Zhan-Ling Ma ^a ^*

^aCollege of Chemistry and Chemical Engineering of Bohai University, Jinzhou, Liaoning 121000, People's Republic of China
^*Correspondence e-mail: mazhanling69@163.com

(Received 24 November 2009; accepted 26 November 2009; online 28 November 2009)

In the title compound, C₂₀H₁₉N₃O₄·CH₄O·H₂O, the Schiff base molecule is almost planar, with a dihedral angle of 1.2 (1)° between the benzene ring and the quinoline ring system. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring. In the crystal, the methanol and water solvent molecules are linked to the Schiff base molecule 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_r = 415.44
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.052
wR(F²) = 0.126
S = 1.01
3676 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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) x, y, z+1; (ii) x, y, z-1; (iii) -x+1, -y+1, -z+1.

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/S1600536809051034/hb5253sup1.cif

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

checkCIF report

Comment top

8-Hydroxyquinoline and its derivatives have been used widely in analytical chemistry (Bratzel et al., 1972), coordination chemistry (Karmakar et al., 2007), pharmaceutical chemistry (Pierre et al., 2003) and many other topics. As part of our on going search for good extractants of metal ions or a biologically active material, the title compound was obtained in the reaction of quinolin-8-yloxyacetic acid hydrazide and 3,4-dimethoxybenzaldehyde.

The Schiff base molecule of the compound displays a trans configuration with respect to the C=N and C—N bonds(Fig. 1). All the bond lengths are within normal(Allen et al., 1987), and are comparable to those in the related compound (E)-N'-(2,5-Dimethoxybenzylidene)-2-(8- quinolyloxy)acetohydrazide methanol solvate (Wang et al., 2009). The molecule is nearly planar, with a dihedral angle of the benzene ring and the quinoline ring is 1.2 (1)°. The methanol and water solvate molecules are linked to the host via N—H···O, O—H···O and O—H···N hydrogen bonds(Table 1).

Related literature top

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 top

3,4-Dimethoxybenzaldehyde (0.1 mmol, 16.6 mg) and 2-(quinolin-8-yloxy) acetohydrazide (2.18 g, 10 mmol), were dissolved in a 95% ethanol solution (10 ml). The mixture was stirred at room temperature to give a clear colorless solution. Colourless blocks of (I) were formed by gradual evaporation of the solvent over a period of six days at room temperature.

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.

(E)-N'-(3,4-Dimethoxybenzylidene)-2-(8- quinolyloxy)acetohydrazide–methanol–water (1/1/1) top

Crystal data top

C₂₀H₁₉N₃O₄·CH₄O·H₂O	Z = 2
M_r = 415.44	F(000) = 440
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0363P)² + 0.0145P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
3676 reflections	Δρ_max = 0.19 e Å⁻³
273 parameters	Δρ_min = −0.17 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)

Crystal data top

C₂₀H₁₉N₃O₄·CH₄O·H₂O	γ = 82.458 (5)°
M_r = 415.44	V = 1044.4 (4) Å³
Triclinic, P1	Z = 2
a = 8.807 (2) Å	Mo Kα radiation
b = 10.071 (3) Å	µ = 0.10 mm⁻¹
c = 13.121 (3) Å	T = 295 K
α = 68.702 (4)°	0.21 × 0.18 × 0.16 mm
β = 74.552 (3)°

Data collection top

Siemens SMART CCD diffractometer	3676 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1571 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.985	R_int = 0.035
5612 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.01	Δρ_max = 0.19 e Å⁻³
3676 reflections	Δρ_min = −0.17 e Å⁻³
273 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	0.9264 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) x, y, z+1; (ii) x, y, z−1; (iii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉N₃O₄·CH₄O·H₂O
M_r	415.44
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	8.807 (2), 10.071 (3), 13.121 (3)
α, β, γ (°)	68.702 (4), 74.552 (3), 82.458 (5)
V (Å³)	1044.4 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.21 × 0.18 × 0.16

Data collection
Diffractometer	Siemens SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.980, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	5612, 3676, 1571
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.126, 1.01
No. of reflections	3676
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.17

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
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) x, y, z+1; (ii) x, y, z−1; (iii) −x+1, −y+1, −z+1.

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 Google Scholar
Bratzel, M. P., Aaron, J. J., Winefordner, J. D., Schulman, S. G. & Gershon, H. (1972). Anal. Chem. 44, 1240–1245. CrossRef CAS Web of Science Google Scholar
Karmakar, A., Sarma, R. J. & Baruah, J. B. (2007). CrystEngComm, 9, 379–389. Web of Science CSD CrossRef CAS Google Scholar
Pierre, J.-L., Baret, P. & Serratrice, G. (2003). Curr. Med. Chem. 10, 1077–1084. Web of Science CrossRef PubMed CAS 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 IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Wang, S.-Y., Yuan, L., Xu, L., Zhang, Z., Diao, Y.-P. & Lv, D.-C. (2009). Acta Cryst. E65, o1154. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 12| December 2009| Page o3230

doi:10.1107/S1600536809051034

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

(E)-N′-(3,4-Di­meth­oxy­benzyl­­idene)-2-(8-quinol­yl­oxy)acetohydrazide–methanol–water (1/1/1)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

(E)-N′-(3,4-Dimethoxybenzylidene)-2-(8-quinolyloxy)acetohydrazide–methanol–water (1/1/1)