(E)-N′-(3,4,5-Trimethoxy­benzyl­idene)-2-(8-quinol­yloxy)acetohydrazide methanol solvate

Zeng, L.

doi:10.1107/S1600536809051113

organic compounds

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Volume 66| Part 1| January 2010| Page o23

doi:10.1107/S1600536809051113

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(E)-N′-(3,4,5-Trimethoxybenzylidene)-2-(8-quinolyloxy)acetohydrazide methanol solvate

Ling Zeng ^a ^*

^aCollege of Chemistry and Chemical Engineering of Bohai University, Jinzhou, Liaoning 121000, People's Republic of China
^*Correspondence e-mail: zengling1976@163.com

(Received 25 November 2009; accepted 26 November 2009; online 4 December 2009)

In the title compound, C₂₁H₂₁N₃O₅·CH₄O, the quinoline plane and the benzene ring form a dihedral angle of 3.6 (2)°. The methanol solvent molecule is linked with the acetohydrazide molecule via O—H⋯N and N—H⋯O hydrogen bonds. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds help to consolidate the crystal packing, which also exhibits π–π interactions, 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_r = 427.45
Orthorhombic, P n a 2₁
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[F² > 2σ(F²)] = 0.043
wR(F²) = 0.099
S = 1.08
1879 reflections
283 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

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) $[-x+1, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ .

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/S1600536809051113/cv2668sup1.cif

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

checkCIF report

Comment top

Synthesis of 8-hydroxyquinoline and its derivatives have attracted a great interest due to their biological activities and applications in coordination chemistry (Park et al., 2006; Karmakar et al., 2007). In our search for new extractants of metal ions and biologically active materials, the title compound, (I), has been synthesized. We report here its crystal structure.

All bond lengths and angles are normal and comparable to those observed 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 of 3.6 (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. In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) help to consolidate the crystal packing.

Related literature top

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 top

3,4,5-Trimethoxybenzaldehyde (0.1 mmol, 19.6 mg) and 2-(quinolin-8-yloxy) acetohydrazide (21.8 mg, 0.1 mmol), were dissolved in methanol (20 ml). The mixture was stirred at room temperature to give a clear colorless solution. Crystals of the title compound 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. Dashed lines indicate hydrogen bonds.

(E)-N'-(3,4,5-Trimethoxybenzylidene)-2-(8- quinolyloxy)acetohydrazide methanol solvate top

Crystal data top

C₂₁H₂₁N₃O₅·CH₄O	F(000) = 904
M_r = 427.45	D_x = 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

Data collection top

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

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)] = 0.043	H-atom parameters constrained
wR(F²) = 0.099	w = 1/[σ²(F_o²) + (0.0351P)² + 0.0119P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
1879 reflections	Δρ_max = 0.15 e Å⁻³
283 parameters	Δρ_min = −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)

Crystal data top

C₂₁H₂₁N₃O₅·CH₄O	V = 2091.8 (11) Å³
M_r = 427.45	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 13.385 (4) Å	µ = 0.10 mm⁻¹
b = 4.9005 (15) Å	T = 295 K
c = 31.89 (1) Å	0.18 × 0.15 × 0.12 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1879 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1263 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.988	R_int = 0.077
10056 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.08	Δρ_max = 0.15 e Å⁻³
1879 reflections	Δρ_min = −0.16 e Å⁻³
283 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	0.6229 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, z−1/2; (ii) x−1/2, −y+3/2, z; (iii) x+1/2, −y+3/2, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁N₃O₅·CH₄O
M_r	427.45
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	295
a, b, c (Å)	13.385 (4), 4.9005 (15), 31.89 (1)
V (Å³)	2091.8 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.18 × 0.15 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.982, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	10056, 1879, 1263
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.099, 1.08
No. of reflections	1879
No. of parameters	283
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16

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
O6—H6···N1	0.82	2.02	2.814 (5)	163.7
N2—H4···O6	0.86	2.30	3.070 (4)	148.8
C3—H3···O5ⁱ	0.93	2.45	3.340 (6)	159.2
C5—H5···O4ⁱ	0.93	2.52	3.411 (6)	159.7
C19—H19A···O2ⁱⁱ	0.96	2.37	3.196 (6)	144.3
C21—H21A···O3ⁱⁱⁱ	0.96	2.57	3.265 (5)	129.8

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

References

Karmakar, A., Sarma, R. J. & Baruah, J. B. (2007). CrystEngComm, 9, 379–389. Web of Science CSD CrossRef CAS Google Scholar
Park, K. M., Moon, S. T., Kang, Y. J., Kim, H. J., Seo, J. & Lee, S. S. (2006). Inorg. Chem. Commun. 9, 671–674. Web of Science CSD CrossRef 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 CAS 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 66| Part 1| January 2010| Page o23

doi:10.1107/S1600536809051113

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

(E)-N′-(3,4,5-Tri­meth­oxy­benzyl­­idene)-2-(8-quinol­yl­oxy)acetohydrazide methanol solvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

(E)-N′-(3,4,5-Trimethoxybenzylidene)-2-(8-quinolyloxy)acetohydrazide methanol solvate