(E)-N′-(2,5-Dimethoxy­benzyl­idene)-2-(8-quinol­yloxy)acetohydrazide methanol solvate

Wang, S.-Y.; Yuan, L.; Xu, L.; Zhang, Z.; Diao, Y.-P.; Lv, D.-C.

doi:10.1107/S1600536809015165

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1154

doi:10.1107/S1600536809015165

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(E)-N′-(2,5-Dimethoxybenzylidene)-2-(8-quinolyloxy)acetohydrazide methanol solvate

Shou-Yu Wang,^a Liang Yuan,^b Liang Xu,^c Zhen Zhang,^a Yun-Peng Diao ^a,^c ^* and De-Cheng Lv ^a ^*

^aDepartment of Orthopaedics, The First Affiliated Hospital of Dalian Medical University, Dalian 116011, People's Republic of China, ^bDepartment of Orthopaedics, The Second Affiliated Hospital of Dalian Medical University, Dalian 116011, People's Republic of China, and ^cCollege of Pharmacy, Liaoning University of Traditional Chinese Medicine, Dalian 116600, People's Republic of China
^*Correspondence e-mail: lixiaokuan@126.com, diaoyiwen@126.com

(Received 15 April 2009; accepted 23 April 2009; online 30 April 2009)

The two molecules in the asymmetric unit of the title compound, C₂₀H₁₉N₃O₄·CH₄O, are paired via O—H⋯(O,N), N—H⋯O, and C—H⋯O hydrogen bonds. The molecular skeleton of the acetohydrazide molecule is close to planar; the benzene and quinoline mean planes form a dihedral angle of 3.9 (3)°. The crystal packing exhibits weak intermolecular C—H⋯O hydrogen bonds and π–π interactions, indicated by short distances of 3.668 (3) Å, between the centroids of N-containing six-membered rings from neighbouring acetohydrazide molecules.

Related literature

For applications of 8-hydroxyquinoline and its derivatives, see: Park et al. (2006 ); Karmakar et al. (2007 ). For a related structure, see Wen et al. (2005 ).

Experimental

Crystal data

C₂₀H₁₉N₃O₄·CH₄O
M_r = 397.42
Triclinic, $[P \overline 1]$
a = 9.4199 (12) Å
b = 10.8652 (14) Å
c = 11.1721 (14) Å
α = 93.268 (1)°
β = 112.816 (2)°
γ = 107.859 (3)°
V = 982.8 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 295 K
0.22 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.979, T_max = 0.985
5196 measured reflections
3456 independent reflections
2363 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.149
S = 1.03
3456 reflections
263 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O1	0.82	2.53	2.996 (3)	117
O5—H5A⋯N1	0.82	2.06	2.782 (3)	147
N2—H2⋯O5	0.86	2.01	2.856 (3)	166
C12—H12⋯O5	0.93	2.51	3.305 (3)	144
C3—H3⋯O2ⁱ	0.93	2.60	3.220 (3)	125
C20—H20A⋯O2ⁱⁱ	0.96	2.59	3.511 (5)	160
Symmetry codes: (i) x-1, y, z-1; (ii) x+1, y, 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/S1600536809015165/cv2552sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809015165/cv2552Isup2.hkl

checkCIF report

Comment top

Synthesis of 8-hydroxyquinoline and its derivatives have attracted a great interest due to their interesting biological activities and applications in coordination chemistry (Park et al., 2006; Karmakar et al., 2007). As a part of our ongoing search for good extractants of metal ions and biologically active materials, the title compound, (I), was obtained in the reaction of quinolin-8-yloxyacetic acid hydrazide and 2,5-dimethoxybenzaldehyde.

In (I) (Fig. 1), all bond lengths and angles are normal and comparable to those in the related compound N'-(2-fluorobenzylidene) -2-(quinolin-8-yloxy)-acetohydrazide methanol solvate (Wen et al., 2005). The mean planes of the benzene ring and the quinoline rings make a dihedral angle of 3.9 (3)°. In the crystal structure, the methanol molecule is linked to the C₂₀H₁₉N₃O₄ molecule via intermolecular O—H···O, N—H···O, O—H···N and C—H···O hydrogen bonds(Fig. 1 and Table 1). The crystal packing exhibits weak intermolecular C—H···O hydrogen bonds and π–π interactions proved by short distance of 3.668 (3) Å between the centroids of N-containing six-membered rings from the neighbouring molecules L.

Related literature top

For applications of 8-hydroxyquinoline and its derivatives, see: Park et al. (2006); Karmakar et al. (2007). For the crystal structure of related compound, see Wen et al. (2005).

Experimental top

2-(Quinolin-8-yloxy)acetohydrazide (2.18 g, 10 mmol), 2,5-dimethoxybenzaldehyde (1.66 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 study were obtained by slow evaporation of a acetone-methanol (1:1, v/v) solution over a period of 2 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 of (I), with displacement ellipsoids drawn at the 30% probability level. The dashed lines indicate hydrogen bonds.

(E)-N'-(2,5-Dimethoxybenzylidene)-2-(8-quinolyloxy)acetohydrazide methanol solvate top

Crystal data top

C₂₀H₁₉N₃O₄·CH₄O	Z = 2
M_r = 397.42	F(000) = 420
Triclinic, P1	D_x = 1.343 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4199 (12) Å	Cell parameters from 1903 reflections
b = 10.8652 (14) Å	θ = 2.5–26.9°
c = 11.1721 (14) Å	µ = 0.10 mm⁻¹
α = 93.268 (1)°	T = 295 K
β = 112.816 (2)°	Block, colorless
γ = 107.859 (3)°	0.22 × 0.18 × 0.16 mm
V = 982.8 (2) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3456 independent reflections
Radiation source: fine-focus sealed tube	2363 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
T_min = 0.979, T_max = 0.985	k = −12→12
5196 measured reflections	l = −13→10

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0685P)² + 0.304P] where P = (F_o² + 2F_c²)/3
3456 reflections	(Δ/σ)_max < 0.001
263 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₀H₁₉N₃O₄·CH₄O	γ = 107.859 (3)°
M_r = 397.42	V = 982.8 (2) Å³
Triclinic, P1	Z = 2
a = 9.4199 (12) Å	Mo Kα radiation
b = 10.8652 (14) Å	µ = 0.10 mm⁻¹
c = 11.1721 (14) Å	T = 295 K
α = 93.268 (1)°	0.22 × 0.18 × 0.16 mm
β = 112.816 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3456 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2363 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.985	R_int = 0.019
5196 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.03	Δρ_max = 0.38 e Å⁻³
3456 reflections	Δρ_min = −0.33 e Å⁻³
263 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	−0.24162 (17)	0.13371 (15)	0.32912 (13)	0.0535 (4)
O2	0.0642 (2)	0.1461 (2)	0.64429 (16)	0.0858 (6)
O3	0.4628 (2)	0.39500 (19)	0.28395 (18)	0.0788 (5)
O4	0.8736 (2)	0.3699 (2)	0.7849 (2)	0.0949 (7)
O5	−0.0293 (3)	0.2135 (3)	0.1843 (2)	0.1266 (11)
H5A	−0.1081	0.2324	0.1818	0.190*
N1	−0.3582 (2)	0.19146 (18)	0.08689 (17)	0.0528 (5)
N2	0.0876 (2)	0.19807 (18)	0.45814 (17)	0.0560 (5)
H2	0.0371	0.2020	0.3766	0.067*
N3	0.2580 (2)	0.23818 (18)	0.51768 (18)	0.0558 (5)
C1	−0.4175 (3)	0.2184 (2)	−0.0328 (2)	0.0601 (6)
H1	−0.3428	0.2594	−0.0664	0.072*
C2	−0.5851 (3)	0.1892 (2)	−0.1121 (2)	0.0643 (7)
H2A	−0.6203	0.2104	−0.1956	0.077*
C3	−0.6951 (3)	0.1293 (2)	−0.0644 (2)	0.0627 (6)
H3	−0.8073	0.1086	−0.1154	0.075*
C4	−0.6394 (3)	0.0981 (2)	0.0630 (2)	0.0536 (6)
C5	−0.7479 (3)	0.0345 (3)	0.1181 (3)	0.0662 (7)
H5	−0.8608	0.0141	0.0709	0.079*
C6	−0.6890 (3)	0.0033 (3)	0.2383 (3)	0.0693 (7)
H6	−0.7616	−0.0393	0.2731	0.083*
C7	−0.5183 (3)	0.0346 (2)	0.3117 (2)	0.0575 (6)
H7	−0.4796	0.0116	0.3941	0.069*
C8	−0.4090 (2)	0.0981 (2)	0.2636 (2)	0.0474 (5)
C9	−0.4680 (3)	0.1308 (2)	0.1355 (2)	0.0473 (5)
C10	−0.1828 (3)	0.1048 (2)	0.4579 (2)	0.0543 (6)
H10A	−0.2262	0.0101	0.4509	0.065*
H10B	−0.2240	0.1450	0.5106	0.065*
C11	0.0023 (3)	0.1532 (2)	0.5280 (2)	0.0549 (6)
C12	0.3277 (3)	0.2839 (2)	0.4443 (2)	0.0603 (6)
H12	0.2622	0.2859	0.3576	0.072*
C13	0.5061 (3)	0.3334 (2)	0.4906 (2)	0.0568 (6)
C14	0.5723 (3)	0.3921 (2)	0.4061 (3)	0.0625 (6)
C15	0.7399 (4)	0.4419 (3)	0.4488 (3)	0.0800 (8)
H15	0.7843	0.4798	0.3926	0.096*
C16	0.8436 (4)	0.4366 (3)	0.5739 (3)	0.0842 (9)
H16	0.9572	0.4722	0.6020	0.101*
C17	0.7807 (3)	0.3791 (3)	0.6577 (3)	0.0701 (7)
C18	0.6115 (3)	0.3272 (2)	0.6158 (3)	0.0637 (6)
H18	0.5682	0.2879	0.6720	0.076*
C19	0.5240 (4)	0.4653 (3)	0.2014 (3)	0.0892 (9)
H19A	0.5871	0.5557	0.2460	0.134*
H19B	0.4335	0.4616	0.1206	0.134*
H19C	0.5931	0.4265	0.1814	0.134*
C20	1.0484 (4)	0.4126 (4)	0.8254 (4)	0.1123 (12)
H20A	1.0716	0.3572	0.7710	0.168*
H20B	1.1020	0.4068	0.9164	0.168*
H20C	1.0885	0.5023	0.8159	0.168*
C21	0.0330 (4)	0.2797 (4)	0.1045 (3)	0.0957 (10)
H21A	0.0494	0.3715	0.1245	0.144*
H21B	−0.0432	0.2434	0.0133	0.144*
H21C	0.1365	0.2705	0.1197	0.144*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0409 (8)	0.0744 (10)	0.0410 (8)	0.0212 (7)	0.0117 (7)	0.0201 (7)
O2	0.0538 (10)	0.1467 (18)	0.0475 (10)	0.0343 (11)	0.0108 (8)	0.0388 (11)
O3	0.0767 (12)	0.0900 (13)	0.0686 (12)	0.0228 (10)	0.0340 (10)	0.0253 (10)
O4	0.0494 (11)	0.1275 (18)	0.0953 (15)	0.0243 (11)	0.0215 (10)	0.0391 (13)
O5	0.0554 (12)	0.231 (3)	0.0757 (14)	0.0286 (15)	0.0217 (11)	0.0755 (17)
N1	0.0500 (11)	0.0604 (11)	0.0436 (10)	0.0208 (9)	0.0143 (9)	0.0138 (9)
N2	0.0412 (10)	0.0703 (12)	0.0432 (10)	0.0135 (9)	0.0089 (8)	0.0160 (9)
N3	0.0412 (10)	0.0607 (12)	0.0548 (11)	0.0126 (9)	0.0139 (9)	0.0118 (9)
C1	0.0621 (15)	0.0668 (15)	0.0468 (13)	0.0245 (12)	0.0164 (12)	0.0188 (11)
C2	0.0704 (17)	0.0686 (16)	0.0465 (13)	0.0317 (13)	0.0112 (12)	0.0177 (11)
C3	0.0519 (14)	0.0673 (15)	0.0549 (14)	0.0260 (12)	0.0052 (12)	0.0122 (12)
C4	0.0458 (12)	0.0561 (13)	0.0493 (12)	0.0219 (10)	0.0083 (10)	0.0069 (10)
C5	0.0405 (13)	0.0817 (17)	0.0658 (16)	0.0215 (12)	0.0121 (12)	0.0161 (13)
C6	0.0475 (14)	0.0895 (19)	0.0670 (16)	0.0188 (13)	0.0245 (12)	0.0199 (14)
C7	0.0506 (13)	0.0723 (16)	0.0487 (13)	0.0231 (12)	0.0186 (11)	0.0167 (11)
C8	0.0396 (12)	0.0538 (12)	0.0434 (11)	0.0181 (10)	0.0115 (10)	0.0068 (9)
C9	0.0452 (12)	0.0485 (12)	0.0431 (11)	0.0191 (10)	0.0124 (10)	0.0071 (9)
C10	0.0471 (13)	0.0720 (15)	0.0431 (12)	0.0235 (11)	0.0154 (10)	0.0214 (11)
C11	0.0467 (13)	0.0679 (15)	0.0437 (12)	0.0211 (11)	0.0117 (10)	0.0174 (11)
C12	0.0515 (14)	0.0667 (15)	0.0543 (14)	0.0162 (11)	0.0181 (12)	0.0106 (11)
C13	0.0510 (14)	0.0536 (13)	0.0624 (15)	0.0152 (11)	0.0240 (12)	0.0073 (11)
C14	0.0608 (15)	0.0559 (14)	0.0722 (16)	0.0179 (12)	0.0324 (13)	0.0094 (12)
C15	0.0690 (18)	0.088 (2)	0.094 (2)	0.0265 (15)	0.0457 (17)	0.0337 (17)
C16	0.0548 (16)	0.093 (2)	0.108 (2)	0.0191 (15)	0.0427 (17)	0.0303 (18)
C17	0.0496 (15)	0.0756 (17)	0.0789 (18)	0.0232 (13)	0.0203 (14)	0.0169 (14)
C18	0.0540 (15)	0.0660 (15)	0.0709 (16)	0.0177 (12)	0.0292 (13)	0.0139 (12)
C19	0.102 (2)	0.088 (2)	0.0793 (19)	0.0258 (18)	0.0458 (18)	0.0277 (16)
C20	0.0522 (18)	0.155 (3)	0.114 (3)	0.033 (2)	0.0210 (18)	0.041 (2)
C21	0.076 (2)	0.121 (3)	0.082 (2)	0.0229 (18)	0.0332 (17)	0.0275 (19)

Geometric parameters (Å, º) top

O1—C8	1.367 (2)	C7—C8	1.364 (3)
O1—C10	1.420 (2)	C7—H7	0.9300
O2—C11	1.219 (3)	C8—C9	1.430 (3)
O3—C14	1.364 (3)	C10—C11	1.504 (3)
O3—C19	1.410 (3)	C10—H10A	0.9700
O4—C17	1.378 (3)	C10—H10B	0.9700
O4—C20	1.435 (3)	C12—C13	1.456 (3)
O5—C21	1.371 (3)	C12—H12	0.9300
O5—H5A	0.8200	C13—C18	1.386 (3)
N1—C1	1.324 (3)	C13—C14	1.403 (3)
N1—C9	1.363 (3)	C14—C15	1.369 (4)
N2—C11	1.335 (3)	C15—C16	1.378 (4)
N2—N3	1.385 (2)	C15—H15	0.9300
N2—H2	0.8600	C16—C17	1.374 (4)
N3—C12	1.271 (3)	C16—H16	0.9300
C1—C2	1.398 (3)	C17—C18	1.385 (3)
C1—H1	0.9300	C18—H18	0.9300
C2—C3	1.355 (4)	C19—H19A	0.9600
C2—H2A	0.9300	C19—H19B	0.9600
C3—C4	1.414 (3)	C19—H19C	0.9600
C3—H3	0.9300	C20—H20A	0.9600
C4—C9	1.411 (3)	C20—H20B	0.9600
C4—C5	1.415 (3)	C20—H20C	0.9600
C5—C6	1.348 (3)	C21—H21A	0.9600
C5—H5	0.9300	C21—H21B	0.9600
C6—C7	1.408 (3)	C21—H21C	0.9600
C6—H6	0.9300

C8—O1—C10	115.50 (17)	O2—C11—N2	124.4 (2)
C14—O3—C19	118.6 (2)	O2—C11—C10	117.6 (2)
C17—O4—C20	116.1 (2)	N2—C11—C10	117.96 (18)
C21—O5—H5A	109.5	N3—C12—C13	122.5 (2)
C1—N1—C9	117.75 (19)	N3—C12—H12	118.7
C11—N2—N3	119.67 (17)	C13—C12—H12	118.7
C11—N2—H2	120.2	C18—C13—C14	119.4 (2)
N3—N2—H2	120.2	C18—C13—C12	122.2 (2)
C12—N3—N2	114.67 (19)	C14—C13—C12	118.4 (2)
N1—C1—C2	124.2 (2)	O3—C14—C15	123.8 (2)
N1—C1—H1	117.9	O3—C14—C13	116.8 (2)
C2—C1—H1	117.9	C15—C14—C13	119.3 (3)
C3—C2—C1	118.4 (2)	C14—C15—C16	120.8 (3)
C3—C2—H2A	120.8	C14—C15—H15	119.6
C1—C2—H2A	120.8	C16—C15—H15	119.6
C2—C3—C4	120.1 (2)	C17—C16—C15	120.6 (3)
C2—C3—H3	120.0	C17—C16—H16	119.7
C4—C3—H3	120.0	C15—C16—H16	119.7
C9—C4—C3	117.5 (2)	C16—C17—O4	125.0 (2)
C9—C4—C5	119.7 (2)	C16—C17—C18	119.4 (3)
C3—C4—C5	122.8 (2)	O4—C17—C18	115.5 (2)
C6—C5—C4	120.5 (2)	C17—C18—C13	120.4 (2)
C6—C5—H5	119.7	C17—C18—H18	119.8
C4—C5—H5	119.7	C13—C18—H18	119.8
C5—C6—C7	120.5 (2)	O3—C19—H19A	109.5
C5—C6—H6	119.8	O3—C19—H19B	109.5
C7—C6—H6	119.8	H19A—C19—H19B	109.5
C8—C7—C6	121.0 (2)	O3—C19—H19C	109.5
C8—C7—H7	119.5	H19A—C19—H19C	109.5
C6—C7—H7	119.5	H19B—C19—H19C	109.5
C7—C8—O1	124.68 (19)	O4—C20—H20A	109.5
C7—C8—C9	119.8 (2)	O4—C20—H20B	109.5
O1—C8—C9	115.50 (18)	H20A—C20—H20B	109.5
N1—C9—C4	122.07 (19)	O4—C20—H20C	109.5
N1—C9—C8	119.45 (18)	H20A—C20—H20C	109.5
C4—C9—C8	118.5 (2)	H20B—C20—H20C	109.5
O1—C10—C11	113.06 (18)	O5—C21—H21A	109.5
O1—C10—H10A	109.0	O5—C21—H21B	109.5
C11—C10—H10A	109.0	H21A—C21—H21B	109.5
O1—C10—H10B	109.0	O5—C21—H21C	109.5
C11—C10—H10B	109.0	H21A—C21—H21C	109.5
H10A—C10—H10B	107.8	H21B—C21—H21C	109.5

C11—N2—N3—C12	−177.4 (2)	N3—N2—C11—O2	1.0 (4)
C9—N1—C1—C2	0.3 (3)	N3—N2—C11—C10	−177.22 (19)
N1—C1—C2—C3	−0.1 (4)	O1—C10—C11—O2	172.0 (2)
C1—C2—C3—C4	0.2 (4)	O1—C10—C11—N2	−9.6 (3)
C2—C3—C4—C9	−0.6 (3)	N2—N3—C12—C13	178.7 (2)
C2—C3—C4—C5	−179.4 (2)	N3—C12—C13—C18	3.6 (4)
C9—C4—C5—C6	−0.9 (4)	N3—C12—C13—C14	−174.8 (2)
C3—C4—C5—C6	177.9 (2)	C19—O3—C14—C15	−7.1 (4)
C4—C5—C6—C7	0.6 (4)	C19—O3—C14—C13	173.3 (2)
C5—C6—C7—C8	0.7 (4)	C18—C13—C14—O3	179.8 (2)
C6—C7—C8—O1	179.0 (2)	C12—C13—C14—O3	−1.8 (3)
C6—C7—C8—C9	−1.6 (3)	C18—C13—C14—C15	0.2 (4)
C10—O1—C8—C7	−2.3 (3)	C12—C13—C14—C15	178.6 (2)
C10—O1—C8—C9	178.19 (18)	O3—C14—C15—C16	179.5 (3)
C1—N1—C9—C4	−0.7 (3)	C13—C14—C15—C16	−0.9 (4)
C1—N1—C9—C8	179.0 (2)	C14—C15—C16—C17	1.1 (5)
C3—C4—C9—N1	0.8 (3)	C15—C16—C17—O4	−179.3 (3)
C5—C4—C9—N1	179.7 (2)	C15—C16—C17—C18	−0.5 (4)
C3—C4—C9—C8	−178.88 (19)	C20—O4—C17—C16	−6.5 (4)
C5—C4—C9—C8	0.0 (3)	C20—O4—C17—C18	174.7 (3)
C7—C8—C9—N1	−178.5 (2)	C16—C17—C18—C13	−0.2 (4)
O1—C8—C9—N1	1.0 (3)	O4—C17—C18—C13	178.7 (2)
C7—C8—C9—C4	1.2 (3)	C14—C13—C18—C17	0.4 (4)
O1—C8—C9—C4	−179.29 (18)	C12—C13—C18—C17	−178.0 (2)
C8—O1—C10—C11	−176.68 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O1	0.82	2.53	2.996 (3)	117
O5—H5A···N1	0.82	2.06	2.782 (3)	147
N2—H2···O5	0.86	2.01	2.856 (3)	166
C12—H12···O5	0.93	2.51	3.305 (3)	144
C3—H3···O2ⁱ	0.93	2.60	3.220 (3)	125
C20—H20A···O2ⁱⁱ	0.96	2.59	3.511 (5)	160

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉N₃O₄·CH₄O
M_r	397.42
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	9.4199 (12), 10.8652 (14), 11.1721 (14)
α, β, γ (°)	93.268 (1), 112.816 (2), 107.859 (3)
V (Å³)	982.8 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.22 × 0.18 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.979, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	5196, 3456, 2363
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.149, 1.03
No. of reflections	3456
No. of parameters	263
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.33

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—H5A···O1	0.82	2.53	2.996 (3)	116.9
O5—H5A···N1	0.82	2.06	2.782 (3)	147.0
N2—H2···O5	0.86	2.01	2.856 (3)	166.1
C12—H12···O5	0.93	2.51	3.305 (3)	143.9
C3—H3···O2ⁱ	0.93	2.60	3.220 (3)	124.8
C20—H20A···O2ⁱⁱ	0.96	2.59	3.511 (5)	160.2

Symmetry codes: (i) x−1, y, z−1; (ii) x+1, y, 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
Wen, Y.-H., Zhang, S.-S., Li, M.-J. & Li, X.-M. (2005). Acta Cryst. E61, o2045–o2046. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 5| May 2009| Page o1154

doi:10.1107/S1600536809015165

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

(E)-N′-(2,5-Di­meth­oxy­benzyl­­idene)-2-(8-quinol­yl­oxy)acetohydrazide methanol solvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

(E)-N′-(2,5-Dimethoxybenzylidene)-2-(8-quinolyloxy)acetohydrazide methanol solvate