(E)-N'-(4-Nitro-benzyl-idene)-2-(8-quinol-yloxy)acetohydrazide methanol solvate.

In the title compound, C(18)H(14)N(4)O(4)·CH(3)OH, the mean planes of the benzene ring and the quinoline ring system make a dihedral angle of 15.5 (2)°. The methanol solvent mol-ecule 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 mol-ecules lie in layers approximately parallel to (101) and C-H⋯O inter-actions exist between mol-ecules 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 = 382.37

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.195

S = 1.00

3258 reflections

255 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.26 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/S1600536809015992/bi2363sup1.cif

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

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

C18H14N4O4·CH4O	F(000) = 800
Mr = 382.37	Dx = 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

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

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(Fo2) + (0.1106P)2 + 0.0143P] where P = (Fo2 + 2Fc2)/3
3258 reflections	(Δ/σ)max < 0.001
255 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.26 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	0.1624 (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*

	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)

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)

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

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) ; (ii) .