(E)-N'-(3,4,5-Trimethoxy-benzyl-idene)-2-(8-quinol-yloxy)acetohydrazide methanol solvate.

In the title compound, C(21)H(21)N(3)O(5)·CH(4)O, the quinoline plane and the benzene ring form a dihedral angle of 3.6 (2)°. The methanol solvent mol-ecule is linked with the acetohydrazide mol-ecule via O-H⋯N and N-H⋯O hydrogen bonds. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds help to consolidate the crystal packing, which also exhibits π-π inter-actions, as indicated by short distances of 3.739 (4) Å between the centroids of the aromatic rings.

Related literature

For applications of 8-hydroxy­quinoline derivatives, see: Park et al. (2006 ▶); Karmakar et al. (2007 ▶). For a related structure, see Wang et al. (2009 ▶).

Experimental

Crystal data

C21H21N3O5·CH4O

M = 427.45

Orthorhombic,

a = 13.385 (4) Å

b = 4.9005 (15) Å

c = 31.89 (1) Å

V = 2091.8 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.18 × 0.15 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.982, T max = 0.988

10056 measured reflections

1879 independent reflections

1263 reflections with I > 2σ(I)

R int = 0.077

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.099

S = 1.08

1879 reflections

283 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 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/S1600536809051113/cv2668sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051113/cv2668Isup2.hkl

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

C21H21N3O5·CH4O	F(000) = 904
Mr = 427.45	Dx = 1.357 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 786 reflections
a = 13.385 (4) Å	θ = 2.6–17.8°
b = 4.9005 (15) Å	µ = 0.10 mm−1
c = 31.89 (1) Å	T = 295 K
V = 2091.8 (11) Å3	Block, colourless
Z = 4	0.18 × 0.15 × 0.12 mm

Bruker SMART CCD area-detector diffractometer	1879 independent reflections
Radiation source: fine-focus sealed tube	1263 reflections with I > 2σ(I)
graphite	Rint = 0.077
φ and ω scans	θmax = 25.1°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→13
Tmin = 0.982, Tmax = 0.988	k = −5→5
10056 measured reflections	l = −37→37

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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.099	w = 1/[σ2(Fo2) + (0.0351P)2 + 0.0119P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1879 reflections	Δρmax = 0.15 e Å−3
283 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: 0.0111 (15)

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	0.6229 (2)	0.7115 (6)	0.13448 (8)	0.0497 (8)
O2	0.6522 (3)	1.1590 (8)	0.22093 (11)	0.0819 (12)
O3	0.1718 (2)	0.3242 (6)	0.34960 (8)	0.0495 (8)
O4	0.2323 (2)	0.6336 (6)	0.41318 (8)	0.0448 (8)
O5	0.3852 (2)	0.9783 (6)	0.40569 (9)	0.0515 (9)
O6	0.4246 (3)	0.4033 (8)	0.16176 (12)	0.0776 (12)
H6	0.4642	0.3998	0.1421	0.116*
N1	0.5266 (3)	0.3563 (9)	0.08495 (12)	0.0543 (11)
N2	0.5580 (3)	0.7798 (8)	0.21461 (10)	0.0475 (10)
H4	0.5427	0.6407	0.1995	0.057*
N3	0.5127 (3)	0.8173 (8)	0.25337 (10)	0.0449 (10)
C1	0.4809 (4)	0.1830 (12)	0.06048 (17)	0.0679 (16)
H1	0.4270	0.0872	0.0716	0.081*
C2	0.5070 (5)	0.1317 (12)	0.01916 (17)	0.0679 (16)
H2	0.4720	0.0042	0.0033	0.082*
C3	0.5852 (4)	0.2727 (12)	0.00229 (15)	0.0635 (15)
H3	0.6037	0.2437	−0.0255	0.076*
C4	0.6372 (4)	0.4592 (10)	0.02669 (14)	0.0481 (12)
C5	0.7184 (4)	0.6099 (12)	0.01122 (15)	0.0610 (15)
H5	0.7386	0.5885	−0.0165	0.073*
C6	0.7676 (4)	0.7867 (11)	0.03669 (15)	0.0597 (14)
H6A	0.8220	0.8836	0.0263	0.072*
C7	0.7376 (4)	0.8255 (11)	0.07854 (14)	0.0530 (13)
H7	0.7724	0.9470	0.0955	0.064*
C8	0.6581 (3)	0.6872 (10)	0.09433 (12)	0.0436 (12)
C9	0.6056 (3)	0.4985 (10)	0.06885 (13)	0.0439 (12)
C10	0.6703 (3)	0.9191 (9)	0.15890 (14)	0.0486 (12)
H10A	0.6671	1.0901	0.1436	0.058*
H10B	0.7402	0.8724	0.1624	0.058*
C11	0.6250 (3)	0.9590 (11)	0.20091 (14)	0.0479 (12)
C12	0.4417 (3)	0.6516 (10)	0.26137 (14)	0.0463 (12)
H12	0.4241	0.5212	0.2415	0.056*
C13	0.3880 (3)	0.6625 (10)	0.30083 (12)	0.0417 (12)
C14	0.3068 (3)	0.4905 (9)	0.30537 (12)	0.0421 (11)
H14	0.2883	0.3768	0.2833	0.050*
C15	0.2527 (3)	0.4860 (9)	0.34250 (12)	0.0389 (11)
C16	0.2808 (3)	0.6550 (10)	0.37560 (12)	0.0374 (11)
C17	0.3629 (3)	0.8264 (9)	0.37111 (12)	0.0405 (11)
C18	0.4170 (3)	0.8321 (9)	0.33362 (12)	0.0409 (12)
H18	0.4717	0.9477	0.3306	0.049*
C19	0.1410 (4)	0.1460 (10)	0.31644 (14)	0.0520 (12)
H19A	0.1206	0.2525	0.2927	0.078*
H19B	0.0861	0.0359	0.3258	0.078*
H19C	0.1957	0.0301	0.3086	0.078*
C20	0.1689 (4)	0.8559 (10)	0.42331 (16)	0.0624 (15)
H20A	0.2052	1.0238	0.4203	0.094*
H20B	0.1462	0.8378	0.4517	0.094*
H20C	0.1125	0.8567	0.4047	0.094*
C21	0.4632 (3)	1.1764 (10)	0.40269 (14)	0.0513 (13)
H21A	0.5264	1.0852	0.4002	0.077*
H21B	0.4633	1.2881	0.4274	0.077*
H21C	0.4524	1.2889	0.3785	0.077*
C22	0.3780 (4)	0.1473 (12)	0.1656 (2)	0.0755 (16)
H22A	0.4269	0.0056	0.1624	0.113*
H22B	0.3280	0.1286	0.1442	0.113*
H22C	0.3472	0.1329	0.1927	0.113*

	U11	U22	U33	U12	U13	U23
O1	0.0574 (19)	0.061 (2)	0.0310 (16)	−0.0138 (17)	0.0085 (14)	−0.0099 (15)
O2	0.104 (3)	0.092 (3)	0.050 (2)	−0.048 (2)	0.0258 (19)	−0.030 (2)
O3	0.052 (2)	0.058 (2)	0.0388 (17)	−0.0123 (18)	0.0051 (14)	−0.0016 (16)
O4	0.0519 (19)	0.052 (2)	0.0299 (16)	0.0046 (16)	0.0083 (14)	0.0080 (15)
O5	0.0585 (19)	0.061 (2)	0.0350 (17)	−0.0140 (19)	0.0038 (15)	−0.0064 (16)
O6	0.088 (3)	0.080 (3)	0.064 (3)	−0.023 (2)	0.018 (2)	−0.018 (2)
N1	0.056 (2)	0.059 (3)	0.048 (2)	−0.009 (2)	0.000 (2)	−0.008 (2)
N2	0.058 (2)	0.054 (3)	0.031 (2)	−0.001 (2)	0.0097 (17)	−0.0052 (18)
N3	0.051 (2)	0.057 (3)	0.0264 (19)	0.003 (2)	0.0121 (18)	−0.0002 (18)
C1	0.063 (3)	0.080 (4)	0.060 (3)	−0.016 (3)	0.000 (3)	−0.019 (3)
C2	0.080 (4)	0.073 (4)	0.052 (3)	−0.001 (4)	−0.011 (3)	−0.022 (3)
C3	0.077 (4)	0.076 (4)	0.037 (3)	0.017 (3)	−0.007 (3)	−0.010 (3)
C4	0.064 (3)	0.048 (3)	0.033 (3)	0.014 (3)	−0.001 (2)	−0.005 (2)
C5	0.077 (4)	0.070 (4)	0.036 (3)	0.013 (3)	0.010 (3)	−0.007 (3)
C6	0.067 (3)	0.069 (4)	0.043 (3)	0.004 (3)	0.017 (3)	0.002 (3)
C7	0.058 (3)	0.065 (4)	0.036 (3)	−0.004 (3)	0.012 (2)	−0.008 (2)
C8	0.052 (3)	0.052 (3)	0.027 (2)	−0.001 (3)	0.005 (2)	−0.003 (2)
C9	0.051 (3)	0.043 (3)	0.038 (3)	0.007 (3)	0.002 (2)	0.000 (2)
C10	0.052 (3)	0.060 (3)	0.034 (2)	−0.013 (3)	0.005 (2)	−0.010 (2)
C11	0.046 (3)	0.062 (4)	0.035 (3)	−0.010 (3)	0.006 (2)	−0.009 (3)
C12	0.051 (3)	0.055 (3)	0.033 (2)	−0.005 (3)	0.008 (2)	−0.003 (2)
C13	0.041 (3)	0.052 (3)	0.032 (2)	0.002 (2)	0.005 (2)	0.001 (2)
C14	0.047 (3)	0.047 (3)	0.033 (2)	−0.001 (2)	0.0023 (19)	−0.003 (2)
C15	0.037 (3)	0.043 (3)	0.037 (3)	0.001 (2)	0.0049 (19)	0.010 (2)
C16	0.041 (3)	0.042 (3)	0.028 (2)	0.003 (2)	0.0052 (19)	0.002 (2)
C17	0.046 (3)	0.047 (3)	0.029 (2)	0.007 (2)	−0.0021 (19)	0.001 (2)
C18	0.043 (3)	0.047 (3)	0.032 (2)	0.001 (2)	0.004 (2)	0.004 (2)
C19	0.057 (3)	0.058 (3)	0.041 (3)	−0.015 (3)	−0.005 (2)	−0.001 (3)
C20	0.070 (3)	0.058 (4)	0.059 (3)	0.002 (3)	0.025 (3)	0.002 (3)
C21	0.050 (3)	0.050 (3)	0.053 (3)	−0.007 (3)	−0.003 (2)	−0.010 (2)
C22	0.069 (4)	0.069 (4)	0.088 (4)	−0.001 (3)	−0.003 (3)	0.008 (3)

O1—C8	1.369 (5)	C7—C8	1.358 (6)
O1—C10	1.429 (5)	C7—H7	0.9300
O2—C11	1.225 (5)	C8—C9	1.418 (6)
O3—C15	1.360 (5)	C10—C11	1.483 (6)
O3—C19	1.432 (5)	C10—H10A	0.9700
O4—C16	1.367 (5)	C10—H10B	0.9700
O4—C20	1.418 (5)	C12—C13	1.450 (6)
O5—C17	1.364 (5)	C12—H12	0.9300
O5—C21	1.429 (5)	C13—C14	1.382 (6)
O6—C22	1.407 (6)	C13—C18	1.391 (6)
O6—H6	0.8200	C14—C15	1.389 (5)
N1—C1	1.306 (6)	C14—H14	0.9300
N1—C9	1.366 (6)	C15—C16	1.394 (6)
N2—C11	1.329 (5)	C16—C17	1.390 (6)
N2—N3	1.389 (5)	C17—C18	1.398 (6)
N2—H4	0.8600	C18—H18	0.9300
N3—C12	1.275 (5)	C19—H19A	0.9600
C1—C2	1.386 (7)	C19—H19B	0.9600
C1—H1	0.9300	C19—H19C	0.9600
C2—C3	1.365 (8)	C20—H20A	0.9600
C2—H2	0.9300	C20—H20B	0.9600
C3—C4	1.387 (7)	C20—H20C	0.9600
C3—H3	0.9300	C21—H21A	0.9600
C4—C5	1.404 (7)	C21—H21B	0.9600
C4—C9	1.422 (6)	C21—H21C	0.9600
C5—C6	1.358 (7)	C22—H22A	0.9600
C5—H5	0.9300	C22—H22B	0.9600
C6—C7	1.407 (6)	C22—H22C	0.9600
C6—H6A	0.9300
C8—O1—C10	114.8 (3)	N3—C12—C13	121.3 (4)
C15—O3—C19	117.5 (3)	N3—C12—H12	119.4
C16—O4—C20	115.1 (3)	C13—C12—H12	119.4
C17—O5—C21	118.5 (3)	C14—C13—C18	120.3 (4)
C22—O6—H6	109.5	C14—C13—C12	117.3 (4)
C1—N1—C9	118.0 (4)	C18—C13—C12	122.4 (4)
C11—N2—N3	120.0 (4)	C13—C14—C15	120.6 (4)
C11—N2—H4	120.0	C13—C14—H14	119.7
N3—N2—H4	120.0	C15—C14—H14	119.7
C12—N3—N2	114.8 (4)	O3—C15—C14	124.5 (4)
N1—C1—C2	124.6 (5)	O3—C15—C16	115.8 (4)
N1—C1—H1	117.7	C14—C15—C16	119.7 (4)
C2—C1—H1	117.7	O4—C16—C17	120.8 (4)
C3—C2—C1	118.4 (5)	O4—C16—C15	119.3 (4)
C3—C2—H2	120.8	C17—C16—C15	119.6 (3)
C1—C2—H2	120.8	O5—C17—C16	114.8 (3)
C2—C3—C4	119.8 (5)	O5—C17—C18	124.5 (4)
C2—C3—H3	120.1	C16—C17—C18	120.6 (4)
C4—C3—H3	120.1	C13—C18—C17	119.1 (4)
C3—C4—C5	122.5 (5)	C13—C18—H18	120.5
C3—C4—C9	118.1 (5)	C17—C18—H18	120.5
C5—C4—C9	119.4 (5)	O3—C19—H19A	109.5
C6—C5—C4	120.1 (5)	O3—C19—H19B	109.5
C6—C5—H5	120.0	H19A—C19—H19B	109.5
C4—C5—H5	120.0	O3—C19—H19C	109.5
C5—C6—C7	121.0 (5)	H19A—C19—H19C	109.5
C5—C6—H6A	119.5	H19B—C19—H19C	109.5
C7—C6—H6A	119.5	O4—C20—H20A	109.5
C8—C7—C6	120.6 (5)	O4—C20—H20B	109.5
C8—C7—H7	119.7	H20A—C20—H20B	109.5
C6—C7—H7	119.7	O4—C20—H20C	109.5
C7—C8—O1	124.9 (4)	H20A—C20—H20C	109.5
C7—C8—C9	120.1 (4)	H20B—C20—H20C	109.5
O1—C8—C9	115.0 (4)	O5—C21—H21A	109.5
N1—C9—C8	120.1 (4)	O5—C21—H21B	109.5
N1—C9—C4	121.1 (4)	H21A—C21—H21B	109.5
C8—C9—C4	118.9 (4)	O5—C21—H21C	109.5
O1—C10—C11	113.9 (4)	H21A—C21—H21C	109.5
O1—C10—H10A	108.8	H21B—C21—H21C	109.5
C11—C10—H10A	108.8	O6—C22—H22A	109.5
O1—C10—H10B	108.8	O6—C22—H22B	109.5
C11—C10—H10B	108.8	H22A—C22—H22B	109.5
H10A—C10—H10B	107.7	O6—C22—H22C	109.5
O2—C11—N2	123.9 (4)	H22A—C22—H22C	109.5
O2—C11—C10	117.0 (4)	H22B—C22—H22C	109.5
N2—C11—C10	119.1 (4)
C11—N2—N3—C12	172.4 (4)	O1—C10—C11—O2	−169.6 (4)
C9—N1—C1—C2	0.2 (8)	O1—C10—C11—N2	10.2 (7)
N1—C1—C2—C3	−0.7 (9)	N2—N3—C12—C13	179.2 (4)
C1—C2—C3—C4	0.8 (8)	N3—C12—C13—C14	174.7 (4)
C2—C3—C4—C5	179.8 (5)	N3—C12—C13—C18	−7.0 (7)
C2—C3—C4—C9	−0.6 (7)	C18—C13—C14—C15	0.5 (7)
C3—C4—C5—C6	−179.0 (5)	C12—C13—C14—C15	178.9 (4)
C9—C4—C5—C6	1.5 (7)	C19—O3—C15—C14	0.2 (6)
C4—C5—C6—C7	−1.0 (8)	C19—O3—C15—C16	−179.5 (4)
C5—C6—C7—C8	−0.3 (8)	C13—C14—C15—O3	179.8 (4)
C6—C7—C8—O1	−179.7 (4)	C13—C14—C15—C16	−0.4 (6)
C6—C7—C8—C9	1.0 (7)	C20—O4—C16—C17	76.2 (5)
C10—O1—C8—C7	6.0 (6)	C20—O4—C16—C15	−109.2 (5)
C10—O1—C8—C9	−174.7 (4)	O3—C15—C16—O4	5.0 (6)
C1—N1—C9—C8	−179.4 (5)	C14—C15—C16—O4	−174.7 (4)
C1—N1—C9—C4	0.0 (7)	O3—C15—C16—C17	179.7 (4)
C7—C8—C9—N1	179.0 (4)	C14—C15—C16—C17	0.0 (6)
O1—C8—C9—N1	−0.3 (6)	C21—O5—C17—C16	−174.9 (4)
C7—C8—C9—C4	−0.5 (6)	C21—O5—C17—C18	6.1 (6)
O1—C8—C9—C4	−179.8 (4)	O4—C16—C17—O5	−4.0 (6)
C3—C4—C9—N1	0.2 (6)	C15—C16—C17—O5	−178.6 (4)
C5—C4—C9—N1	179.7 (5)	O4—C16—C17—C18	175.1 (4)
C3—C4—C9—C8	179.7 (4)	C15—C16—C17—C18	0.5 (6)
C5—C4—C9—C8	−0.8 (6)	C14—C13—C18—C17	−0.1 (7)
C8—O1—C10—C11	174.8 (4)	C12—C13—C18—C17	−178.4 (4)
N3—N2—C11—O2	1.5 (7)	O5—C17—C18—C13	178.6 (4)
N3—N2—C11—C10	−178.3 (4)	C16—C17—C18—C13	−0.4 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···N1	0.82	2.02	2.814 (5)	164
N2—H4···O6	0.86	2.30	3.070 (4)	149
C3—H3···O5i	0.93	2.45	3.340 (6)	159
C5—H5···O4i	0.93	2.52	3.411 (6)	160
C19—H19A···O2ii	0.96	2.37	3.196 (6)	144
C21—H21A···O3iii	0.96	2.57	3.265 (5)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6⋯N1	0.82	2.02	2.814 (5)	164
N2—H4⋯O6	0.86	2.30	3.070 (4)	149
C3—H3⋯O5i	0.93	2.45	3.340 (6)	159
C5—H5⋯O4i	0.93	2.52	3.411 (6)	160
C19—H19A⋯O2ii	0.96	2.37	3.196 (6)	144
C21—H21A⋯O3iii	0.96	2.57	3.265 (5)	130

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