(E)-N′-(4-Nitro­benzyl­idene)-2-(8-quinol­yloxy)acetohydrazide methanol solvate

Ren, C.-Y.

doi:10.1107/S1600536809015992

organic compounds

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Volume 65| Part 6| June 2009| Page o1212

doi:10.1107/S1600536809015992

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(E)-N′-(4-Nitrobenzylidene)-2-(8-quinolyloxy)acetohydrazide methanol solvate

Chun-Yan Ren ^a ^*

^aCollege of Chemistry and Pharmacy, Qingdao Agricultural University, Shandong 266109, People's Republic of China
^*Correspondence e-mail: furbear01@163.com

(Received 1 April 2009; accepted 28 April 2009; online 7 May 2009)

In the title compound, C₁₈H₁₄N₄O₄·CH₃OH, the mean planes of the benzene ring and the quinoline ring system make a dihedral angle of 15.5 (2)°. The methanol solvent molecule forms an O—H⋯N hydrogen bond to the quinoline ring system and accepts an N—H⋯O hydrogen bond from the hydrazide NH group. The molecules lie in layers approximately parallel to (101) and C—H⋯O interactions exist between molecules within the layers.

Related literature

For the coordination chemistry of 8-hydroxyquinoline and its derivatives, see: Chen & Shi (1998 ); Mona & Wageih (2002 ). For a related structure, see: Tan (2009 ).

Experimental

Crystal data

C₁₈H₁₄N₄O₄·CH₄O
M_r = 382.37
Monoclinic, P 2₁ /c
a = 11.345 (10) Å
b = 11.559 (11) Å
c = 16.234 (12) Å
β = 120.06 (5)°
V = 1843 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 295 K
0.20 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.980, T_max = 0.984
9196 measured reflections
3258 independent reflections
1872 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.195
S = 1.00
3258 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯N1	0.82	2.02	2.817 (4)	164
N2—H2⋯O5	0.86	2.08	2.919 (4)	164
C17—H17⋯O3ⁱ	0.93	2.53	3.287 (5)	139
C18—H18⋯O4ⁱ	0.93	2.48	3.329 (5)	152
C3—H3⋯O2ⁱⁱ	0.93	2.58	3.233 (5)	128
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x, y+1, 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/S1600536809015992/bi2363sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809015992/bi2363Isup2.hkl

checkCIF report

Comment top

8-Hydroxyquinoline and its derivatives are well-known ligands in coordination chemistry (Chen & Shi, 1998; Mona & Wageih, 2002). In our search for new extractants of metal ions and biologically active materials, the title compound has been synthesized. In the crystal structure, all bond lengths and angles are normal and comparable to those in the related compound (E)-N'-[1-(4-hydroxyphenyl) ethylidene]-2-(quinolin-8-yloxy)acetohydrazide methanol solvate (Tan, 2009). The mean planes of the benzene ring and the quinoline rings make a dihedral angle of 15.5 (2)°. The methanol molecule is linked to the C₁₈H₁₄N₄O₄ molecule via intermolecular O—H···N and N—H···O hydrogen bonds (Fig. 1). The molecules lie in layers approximately parallel to (101) and C—H···O interactions exist between molecules.

Related literature top

For the coordination chemistry of 8-hydroxyquinoline and its derivatives, see: Chen & Shi (1998); Mona & Wageih (2002). For a related structure, see: Tan (2009).

Experimental top

2-(Quinolin-8-yloxy)acetohydrazide (2.18 g, 10 mmol), 4-nitrobenzaldehyde (1.51 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. Colourless single crystals suitable for X-ray diffraction were obtained by slow evaporation of an acetone-methanol (1:2, v/v) solution over a period of 3 d.

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 with displacement ellipsoids drawn at the 30% probability level for non-H atoms. The dashed lines indicate hydrogen bonds.
	Fig. 2. Intermolecular C—H···O interactions (dashed lines). H atoms have been omitted for clarity.

(E)-N'-(4-Nitrobenzylidene)-2-(8-quinolyloxy)acetohydrazide methanol solvate top

Crystal data top

C₁₈H₁₄N₄O₄·CH₄O	F(000) = 800
M_r = 382.37	D_x = 1.378 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1871 reflections
a = 11.345 (10) Å	θ = 2.3–22.8°
b = 11.559 (11) Å	µ = 0.10 mm⁻¹
c = 16.234 (12) Å	T = 295 K
β = 120.06 (5)°	Block, colorless
V = 1843 (3) Å³	0.20 × 0.18 × 0.16 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3258 independent reflections
Radiation source: fine-focus sealed tube	1872 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→10
T_min = 0.980, T_max = 0.984	k = −12→13
9196 measured reflections	l = −17→19

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.195	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.1106P)² + 0.0143P] where P = (F_o² + 2F_c²)/3
3258 reflections	(Δ/σ)_max < 0.001
255 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₈H₁₄N₄O₄·CH₄O	V = 1843 (3) Å³
M_r = 382.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.345 (10) Å	µ = 0.10 mm⁻¹
b = 11.559 (11) Å	T = 295 K
c = 16.234 (12) Å	0.20 × 0.18 × 0.16 mm
β = 120.06 (5)°

Data collection top

Bruker SMART CCD diffractometer	3258 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1872 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.984	R_int = 0.050
9196 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.195	H-atom parameters constrained
S = 1.00	Δρ_max = 0.21 e Å⁻³
3258 reflections	Δρ_min = −0.26 e Å⁻³
255 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	0.1624 (2)	0.23691 (14)	1.11105 (14)	0.0547 (6)
O2	0.1325 (2)	−0.07065 (16)	1.10099 (16)	0.0694 (7)
O3	0.4318 (3)	−0.4685 (3)	0.7787 (2)	0.1065 (10)
O4	0.5020 (4)	−0.3368 (3)	0.7175 (2)	0.1177 (12)
O5	0.2556 (3)	0.27429 (19)	0.9641 (2)	0.0938 (9)
H5	0.2540	0.3180	1.0033	0.141*
N1	0.2147 (3)	0.45024 (19)	1.06723 (17)	0.0541 (7)
N2	0.2130 (3)	0.05140 (19)	1.02969 (17)	0.0547 (7)
H2	0.2310	0.1214	1.0219	0.066*
N3	0.2403 (3)	−0.0398 (2)	0.98661 (17)	0.0538 (7)
N4	0.4508 (3)	−0.3671 (3)	0.7651 (2)	0.0834 (9)
C1	0.2366 (3)	0.5556 (3)	1.0457 (2)	0.0621 (9)
H1	0.2848	0.5621	1.0135	0.075*
C2	0.1921 (4)	0.6582 (2)	1.0679 (2)	0.0652 (9)
H2A	0.2101	0.7298	1.0504	0.078*
C3	0.1227 (4)	0.6509 (2)	1.1152 (2)	0.0602 (9)
H3	0.0909	0.7176	1.1296	0.072*
C4	0.0985 (3)	0.5417 (2)	1.14255 (19)	0.0510 (8)
C5	0.0322 (3)	0.5278 (3)	1.1966 (2)	0.0605 (9)
H5A	−0.0014	0.5924	1.2123	0.073*
C6	0.0173 (3)	0.4215 (3)	1.2255 (2)	0.0618 (9)
H6	−0.0221	0.4141	1.2635	0.074*
C7	0.0611 (3)	0.3223 (2)	1.1981 (2)	0.0569 (8)
H7	0.0483	0.2498	1.2172	0.068*
C8	0.1224 (3)	0.3306 (2)	1.14367 (19)	0.0474 (7)
C9	0.1459 (3)	0.4422 (2)	1.11638 (18)	0.0456 (7)
C10	0.1252 (3)	0.1263 (2)	1.1307 (2)	0.0564 (8)
H10A	0.0283	0.1263	1.1084	0.068*
H10B	0.1728	0.1145	1.1990	0.068*
C11	0.1570 (3)	0.0270 (2)	1.0849 (2)	0.0521 (8)
C12	0.2988 (3)	−0.0149 (2)	0.9392 (2)	0.0543 (8)
H12	0.3186	0.0619	0.9339	0.065*
C13	0.3350 (3)	−0.1051 (2)	0.89341 (19)	0.0511 (7)
C14	0.2917 (3)	−0.2196 (2)	0.8882 (2)	0.0602 (8)
H14	0.2367	−0.2386	0.9135	0.072*
C15	0.3289 (3)	−0.3049 (3)	0.8461 (2)	0.0630 (9)
H15	0.2996	−0.3808	0.8429	0.076*
C16	0.4108 (3)	−0.2748 (3)	0.8090 (2)	0.0604 (8)
C17	0.4521 (3)	−0.1636 (3)	0.8101 (2)	0.0663 (9)
H17	0.5048	−0.1452	0.7828	0.080*
C18	0.4146 (3)	−0.0785 (3)	0.8526 (2)	0.0610 (9)
H18	0.4427	−0.0026	0.8539	0.073*
C19	0.3321 (4)	0.3241 (3)	0.9278 (3)	0.0858 (12)
H19A	0.2805	0.3851	0.8845	0.129*
H19B	0.3535	0.2664	0.8948	0.129*
H19C	0.4149	0.3552	0.9791	0.129*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0850 (16)	0.0254 (10)	0.0755 (13)	−0.0023 (9)	0.0564 (13)	−0.0003 (9)
O2	0.1058 (19)	0.0270 (11)	0.1018 (17)	−0.0034 (10)	0.0717 (16)	0.0019 (10)
O3	0.121 (3)	0.069 (2)	0.136 (3)	0.0176 (17)	0.069 (2)	−0.0199 (19)
O4	0.142 (3)	0.125 (3)	0.131 (3)	0.015 (2)	0.102 (3)	−0.0246 (19)
O5	0.158 (3)	0.0435 (14)	0.135 (2)	0.0016 (14)	0.115 (2)	0.0028 (14)
N1	0.0780 (19)	0.0345 (13)	0.0612 (15)	−0.0063 (11)	0.0433 (15)	0.0001 (11)
N2	0.0777 (19)	0.0262 (12)	0.0716 (16)	−0.0015 (11)	0.0458 (15)	−0.0002 (11)
N3	0.0709 (18)	0.0345 (13)	0.0654 (15)	0.0027 (11)	0.0412 (15)	−0.0025 (11)
N4	0.080 (2)	0.092 (3)	0.082 (2)	0.0172 (19)	0.0434 (19)	−0.016 (2)
C1	0.089 (3)	0.0418 (18)	0.070 (2)	−0.0116 (16)	0.050 (2)	0.0019 (15)
C2	0.098 (3)	0.0310 (17)	0.0654 (19)	−0.0110 (15)	0.040 (2)	0.0003 (14)
C3	0.087 (3)	0.0307 (16)	0.0627 (19)	−0.0032 (14)	0.037 (2)	−0.0045 (14)
C4	0.068 (2)	0.0328 (16)	0.0490 (16)	−0.0031 (13)	0.0269 (16)	−0.0067 (12)
C5	0.077 (2)	0.0457 (19)	0.069 (2)	0.0000 (15)	0.0442 (19)	−0.0144 (15)
C6	0.082 (3)	0.0512 (19)	0.072 (2)	−0.0057 (16)	0.053 (2)	−0.0076 (16)
C7	0.083 (2)	0.0366 (16)	0.0660 (19)	−0.0038 (14)	0.0488 (19)	0.0007 (14)
C8	0.065 (2)	0.0309 (15)	0.0525 (16)	−0.0004 (12)	0.0337 (16)	−0.0022 (12)
C9	0.062 (2)	0.0324 (15)	0.0469 (15)	−0.0053 (12)	0.0306 (15)	−0.0034 (12)
C10	0.088 (2)	0.0266 (14)	0.0736 (19)	−0.0052 (14)	0.0549 (19)	0.0000 (13)
C11	0.069 (2)	0.0314 (16)	0.0642 (19)	−0.0019 (13)	0.0396 (18)	−0.0020 (13)
C12	0.069 (2)	0.0382 (17)	0.0608 (18)	−0.0017 (14)	0.0365 (18)	0.0021 (13)
C13	0.060 (2)	0.0408 (17)	0.0543 (17)	−0.0012 (13)	0.0301 (16)	0.0014 (13)
C14	0.077 (2)	0.0435 (17)	0.080 (2)	−0.0036 (15)	0.054 (2)	−0.0005 (16)
C15	0.074 (2)	0.0431 (18)	0.079 (2)	−0.0003 (15)	0.044 (2)	−0.0031 (16)
C16	0.062 (2)	0.059 (2)	0.0636 (19)	0.0077 (16)	0.0339 (18)	−0.0069 (16)
C17	0.071 (2)	0.074 (2)	0.069 (2)	−0.0113 (17)	0.046 (2)	−0.0087 (18)
C18	0.069 (2)	0.0535 (19)	0.070 (2)	−0.0128 (15)	0.0422 (19)	−0.0046 (16)
C19	0.100 (3)	0.083 (3)	0.086 (3)	−0.002 (2)	0.055 (3)	0.005 (2)

Geometric parameters (Å, º) top

O1—C8	1.378 (3)	C6—C7	1.407 (4)
O1—C10	1.431 (3)	C6—H6	0.930
O2—C11	1.222 (3)	C7—C8	1.375 (4)
O3—N4	1.232 (4)	C7—H7	0.930
O4—N4	1.227 (4)	C8—C9	1.431 (4)
O5—C19	1.394 (4)	C10—C11	1.506 (4)
O5—H5	0.820	C10—H10A	0.970
N1—C1	1.324 (4)	C10—H10B	0.970
N1—C9	1.371 (4)	C12—C13	1.455 (4)
N2—C11	1.362 (4)	C12—H12	0.930
N2—N3	1.383 (3)	C13—C18	1.395 (4)
N2—H2	0.860	C13—C14	1.399 (4)
N3—C12	1.275 (4)	C14—C15	1.380 (4)
N4—C16	1.476 (4)	C14—H14	0.930
C1—C2	1.406 (4)	C15—C16	1.381 (4)
C1—H1	0.930	C15—H15	0.930
C2—C3	1.350 (5)	C16—C17	1.366 (4)
C2—H2A	0.930	C17—C18	1.385 (4)
C3—C4	1.411 (4)	C17—H17	0.930
C3—H3	0.930	C18—H18	0.930
C4—C9	1.421 (4)	C19—H19A	0.960
C4—C5	1.422 (4)	C19—H19B	0.960
C5—C6	1.355 (4)	C19—H19C	0.960
C5—H5A	0.930

C8—O1—C10	115.2 (2)	O1—C10—C11	113.6 (2)
C19—O5—H5	109.5	O1—C10—H10A	108.8
C1—N1—C9	116.9 (2)	C11—C10—H10A	108.8
C11—N2—N3	118.1 (2)	O1—C10—H10B	108.8
C11—N2—H2	121.0	C11—C10—H10B	108.8
N3—N2—H2	120.9	H10A—C10—H10B	107.7
C12—N3—N2	116.6 (2)	O2—C11—N2	124.3 (3)
O4—N4—O3	124.4 (3)	O2—C11—C10	117.5 (3)
O4—N4—C16	117.1 (4)	N2—C11—C10	118.2 (2)
O3—N4—C16	118.5 (3)	N3—C12—C13	120.8 (3)
N1—C1—C2	124.7 (3)	N3—C12—H12	119.6
N1—C1—H1	117.6	C13—C12—H12	119.6
C2—C1—H1	117.6	C18—C13—C14	118.1 (3)
C3—C2—C1	118.7 (3)	C18—C13—C12	120.0 (3)
C3—C2—H2A	120.7	C14—C13—C12	121.9 (3)
C1—C2—H2A	120.7	C15—C14—C13	121.4 (3)
C2—C3—C4	119.8 (3)	C15—C14—H14	119.3
C2—C3—H3	120.1	C13—C14—H14	119.3
C4—C3—H3	120.1	C14—C15—C16	118.3 (3)
C3—C4—C9	117.9 (3)	C14—C15—H15	120.8
C3—C4—C5	122.8 (3)	C16—C15—H15	120.8
C9—C4—C5	119.3 (3)	C17—C16—C15	122.3 (3)
C6—C5—C4	120.8 (3)	C17—C16—N4	120.0 (3)
C6—C5—H5A	119.6	C15—C16—N4	117.8 (3)
C4—C5—H5A	119.6	C16—C17—C18	119.0 (3)
C5—C6—C7	120.3 (3)	C16—C17—H17	120.5
C5—C6—H6	119.9	C18—C17—H17	120.5
C7—C6—H6	119.9	C17—C18—C13	120.9 (3)
C8—C7—C6	121.3 (3)	C17—C18—H18	119.6
C8—C7—H7	119.4	C13—C18—H18	119.6
C6—C7—H7	119.4	O5—C19—H19A	109.5
C7—C8—O1	124.2 (2)	O5—C19—H19B	109.5
C7—C8—C9	119.6 (2)	H19A—C19—H19B	109.5
O1—C8—C9	116.2 (2)	O5—C19—H19C	109.5
N1—C9—C4	122.0 (2)	H19A—C19—H19C	109.5
N1—C9—C8	119.3 (2)	H19B—C19—H19C	109.5
C4—C9—C8	118.7 (3)

C11—N2—N3—C12	−176.7 (3)	O1—C8—C9—C4	175.8 (3)
C9—N1—C1—C2	−1.3 (5)	C8—O1—C10—C11	173.7 (3)
N1—C1—C2—C3	0.4 (5)	N3—N2—C11—O2	2.0 (5)
C1—C2—C3—C4	1.1 (5)	N3—N2—C11—C10	−179.0 (3)
C2—C3—C4—C9	−1.7 (5)	O1—C10—C11—O2	177.6 (3)
C2—C3—C4—C5	176.8 (3)	O1—C10—C11—N2	−1.4 (4)
C3—C4—C5—C6	−176.6 (3)	N2—N3—C12—C13	178.4 (3)
C9—C4—C5—C6	1.9 (5)	N3—C12—C13—C18	−171.6 (3)
C4—C5—C6—C7	−3.3 (5)	N3—C12—C13—C14	8.8 (5)
C5—C6—C7—C8	1.5 (5)	C18—C13—C14—C15	1.6 (5)
C6—C7—C8—O1	−177.1 (3)	C12—C13—C14—C15	−178.7 (3)
C6—C7—C8—C9	1.8 (5)	C13—C14—C15—C16	0.1 (5)
C10—O1—C8—C7	5.2 (4)	C14—C15—C16—C17	−2.0 (5)
C10—O1—C8—C9	−173.7 (3)	C14—C15—C16—N4	179.4 (3)
C1—N1—C9—C4	0.6 (4)	O4—N4—C16—C17	−11.5 (5)
C1—N1—C9—C8	−178.4 (3)	O3—N4—C16—C17	168.2 (4)
C3—C4—C9—N1	0.9 (4)	O4—N4—C16—C15	167.1 (3)
C5—C4—C9—N1	−177.7 (3)	O3—N4—C16—C15	−13.2 (5)
C3—C4—C9—C8	179.9 (3)	C15—C16—C17—C18	2.1 (5)
C5—C4—C9—C8	1.4 (4)	N4—C16—C17—C18	−179.3 (3)
C7—C8—C9—N1	175.9 (3)	C16—C17—C18—C13	−0.3 (5)
O1—C8—C9—N1	−5.1 (4)	C14—C13—C18—C17	−1.5 (5)
C7—C8—C9—C4	−3.2 (4)	C12—C13—C18—C17	178.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N1	0.82	2.02	2.817 (4)	164
N2—H2···O5	0.86	2.08	2.919 (4)	164
C17—H17···O3ⁱ	0.93	2.53	3.287 (5)	139
C18—H18···O4ⁱ	0.93	2.48	3.329 (5)	152
C3—H3···O2ⁱⁱ	0.93	2.58	3.233 (5)	128

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄N₄O₄·CH₄O
M_r	382.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	11.345 (10), 11.559 (11), 16.234 (12)
β (°)	120.06 (5)
V (Å³)	1843 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.18 × 0.16

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.980, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	9196, 3258, 1872
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.195, 1.00
No. of reflections	3258
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.26

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
O5—H5···N1	0.82	2.02	2.817 (4)	164.2
N2—H2···O5	0.86	2.08	2.919 (4)	163.8
C17—H17···O3ⁱ	0.93	2.53	3.287 (5)	138.6
C18—H18···O4ⁱ	0.93	2.48	3.329 (5)	152.0
C3—H3···O2ⁱⁱ	0.93	2.58	3.233 (5)	127.8

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, y+1, z.

References

Chen, C. H. & Shi, J. M. (1998). Coord. Chem. Rev. 171, 161–174. Web of Science CrossRef CAS Google Scholar
Mona, M. M. & Wageih, G. H. (2002). J. Coord. Chem. 55, 439–457. 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
Tan, J. (2009). Acta Cryst. E65, o651. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 6| June 2009| Page o1212

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

(E)-N′-(4-Nitro­benzyl­­idene)-2-(8-quinol­yl­oxy)acetohydrazide methanol solvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

(E)-N′-(4-Nitrobenzylidene)-2-(8-quinolyloxy)acetohydrazide methanol solvate