4-{(E)-N′-[2-(8-Quinolyloxy)acetyl]hydrazonomethyl}benzoic acid methanol solvate

Ren, C.-Y.

doi:10.1107/S1600536809021576

organic compounds

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Volume 65| Part 7| July 2009| Page o1601

doi:10.1107/S1600536809021576

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4-{(E)-N′-[2-(8-Quinolyloxy)acetyl]hydrazonomethyl}benzoic acid 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 2 April 2009; accepted 6 June 2009; online 17 June 2009)

In the title compound, C₁₉H₁₅N₃O₄·CH₄O, the mean planes of the benzene ring and the quinoline system make a dihedral angle of 6.7 (2)°. The acetohydrazide host molecules are connected via intermolecular O—H⋯O hydrogen bonds into two-dimensional zigzag sheets extending in the ab plane. The methanol solvent molecule is linked to the host molecule via intermolecular N—H⋯O and O—H⋯N hydrogen bonds.

Related literature

For the coordination chemistry of 8-hydroxyquinoline and its derivatives, see: Chen & Shi (1998 ). For a related structure, see: Wen et al. (2005 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₉H₁₅N₃O₄·CH₄O
M_r = 381.38
Monoclinic, P 2₁ /c
a = 10.1166 (18) Å
b = 11.095 (2) Å
c = 18.510 (3) Å
β = 115.896 (7)°
V = 1869.0 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 295 K
0.22 × 0.19 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.979, T_max = 0.982
9663 measured reflections
3302 independent reflections
1666 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.161
S = 1.02
3302 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2ⁱ	0.82	1.88	2.695 (3)	171
O5—H5⋯N1	0.82	1.95	2.765 (3)	171
N2—H2⋯O5	0.86	2.01	2.838 (4)	162
Symmetry code: (i) $[-x+3, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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/S1600536809021576/cs2119sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809021576/cs2119Isup2.hkl

checkCIF report

Comment top

8-Hydroxyquinoline and its derivatives constitute well known ligands in coordination chemistry (Chen & Shi, 1998). As part of our on going search for good extractants of metal ions or a biologically active material, the title compound was obtained in the reaction of quinolin-8-yloxyacetic acid hydrazide and 4-formylbenzoic acid. In the crystal structure of all bond lengths and angles are normal (Allen et al., 1987), and are 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 ring make a dihedral angle of 6.7 (2)°. In the crystal structure, the methanol molecule is linked to the C₁₉H₁₅N₃O₄ host molecule via intermolecular N—H···O and O—H···N hydrogen bonds (Fig. 1). Intermolecular O—H···O hydrogen bonds (Table 1) fuse the molecules into two-dimensional zig-zag sheets along the a*-b* plane (Fig. 2).

Related literature top

For the coordination chemistry of 8-hydroxyquinoline and its derivatives, see: Chen & Shi (1998). For a related structure, see: Wen et al. (2005). For bond-length data, see: Allen et al. (1987).

Experimental top

2-(quinolin-8-yloxy)acetohydrazide (2.18 g, 10 mmol), 4-formylbenzoic acid (1.50 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 (1:2, 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 asymmetric unit structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. The dashed lines indicate hydrogen bonds.
	Fig. 2. The H-bonding sheet from the crystal structure supported via hydrogen bridges (dashed lines), with only relevant H atoms shown for clarity.

4-{(E)-N'-[2-(8-Quinolyloxy)acetyl]hydrazonomethyl}benzoic acid methanol solvate top

Crystal data top

C₁₉H₁₅N₃O₄·CH₄O	F(000) = 800
M_r = 381.38	D_x = 1.355 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1033 reflections
a = 10.1166 (18) Å	θ = 2.9–20.4°
b = 11.095 (2) Å	µ = 0.10 mm⁻¹
c = 18.510 (3) Å	T = 295 K
β = 115.896 (7)°	Block, colorless
V = 1869.0 (6) Å³	0.22 × 0.19 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3302 independent reflections
Radiation source: fine-focus sealed tube	1666 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→12
T_min = 0.979, T_max = 0.982	k = −13→11
9663 measured reflections	l = −22→15

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.161	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0693P)² + 0.0146P] where P = (F_o² + 2F_c²)/3
3302 reflections	(Δ/σ)_max < 0.001
255 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₉H₁₅N₃O₄·CH₄O	V = 1869.0 (6) Å³
M_r = 381.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.1166 (18) Å	µ = 0.10 mm⁻¹
b = 11.095 (2) Å	T = 295 K
c = 18.510 (3) Å	0.22 × 0.19 × 0.18 mm
β = 115.896 (7)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3302 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1666 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.982	R_int = 0.046
9663 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.161	H-atom parameters constrained
S = 1.02	Δρ_max = 0.20 e Å⁻³
3302 reflections	Δρ_min = −0.20 e Å⁻³
255 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.63801 (19)	0.10228 (18)	0.61156 (11)	0.0599 (6)
O2	0.9689 (2)	−0.0368 (2)	0.74781 (14)	0.0785 (7)
O3	1.7457 (2)	0.4174 (2)	0.71168 (15)	0.0813 (7)
H3	1.8346	0.4274	0.7284	0.122*
O4	1.8166 (2)	0.2717 (2)	0.80207 (16)	0.1010 (9)
O5	0.7722 (3)	0.3037 (3)	0.55054 (17)	0.1139 (11)
H5	0.6857	0.2843	0.5343	0.171*
N1	0.4754 (3)	0.2645 (3)	0.50135 (15)	0.0710 (8)
N2	0.9278 (2)	0.1277 (2)	0.66847 (14)	0.0584 (7)
H2	0.8646	0.1762	0.6347	0.070*
N3	1.0764 (2)	0.1439 (2)	0.69304 (14)	0.0571 (7)
C1	0.3936 (4)	0.3439 (4)	0.4474 (2)	0.0946 (12)
H1	0.4414	0.4064	0.4351	0.113*
C2	0.2410 (4)	0.3411 (4)	0.4076 (2)	0.1093 (14)
H2A	0.1892	0.3998	0.3700	0.131*
C3	0.1702 (4)	0.2509 (4)	0.4249 (2)	0.0895 (12)
H3A	0.0682	0.2465	0.3988	0.107*
C4	0.2502 (3)	0.1634 (3)	0.48242 (18)	0.0657 (9)
C5	0.1831 (4)	0.0687 (4)	0.5031 (2)	0.0820 (11)
H5A	0.0813	0.0612	0.4782	0.098*
C6	0.2653 (4)	−0.0124 (3)	0.5593 (2)	0.0830 (11)
H6	0.2192	−0.0747	0.5732	0.100*
C7	0.4194 (3)	−0.0038 (3)	0.5971 (2)	0.0694 (9)
H7	0.4742	−0.0604	0.6356	0.083*
C8	0.4887 (3)	0.0864 (3)	0.57778 (16)	0.0542 (8)
C9	0.4050 (3)	0.1729 (3)	0.51962 (17)	0.0563 (8)
C10	0.7231 (3)	0.0167 (3)	0.67118 (18)	0.0582 (8)
H10A	0.6963	−0.0640	0.6495	0.070*
H10B	0.7007	0.0238	0.7169	0.070*
C11	0.8852 (3)	0.0348 (3)	0.69869 (19)	0.0569 (8)
C12	1.1136 (3)	0.2365 (3)	0.66626 (17)	0.0616 (8)
H12	1.0418	0.2893	0.6324	0.074*
C13	1.2683 (3)	0.2610 (3)	0.68819 (17)	0.0553 (8)
C14	1.3077 (3)	0.3561 (3)	0.65354 (18)	0.0634 (9)
H14	1.2351	0.4054	0.6168	0.076*
C15	1.4531 (3)	0.3789 (3)	0.67266 (17)	0.0611 (8)
H15	1.4774	0.4426	0.6481	0.073*
C16	1.5624 (3)	0.3087 (3)	0.72761 (17)	0.0529 (8)
C17	1.5237 (3)	0.2143 (3)	0.76234 (19)	0.0661 (9)
H17	1.5969	0.1660	0.7996	0.079*
C18	1.3783 (3)	0.1893 (3)	0.74314 (18)	0.0634 (9)
H18	1.3544	0.1246	0.7671	0.076*
C19	1.7212 (3)	0.3295 (3)	0.7518 (2)	0.0640 (9)
C20	0.7908 (5)	0.3609 (5)	0.4924 (3)	0.158 (2)
H20A	0.8434	0.4347	0.5130	0.236*
H20B	0.6967	0.3786	0.4491	0.236*
H20C	0.8459	0.3107	0.4731	0.236*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0316 (11)	0.0766 (15)	0.0663 (12)	−0.0052 (9)	0.0166 (9)	0.0076 (11)
O2	0.0439 (13)	0.0783 (16)	0.1085 (17)	0.0127 (11)	0.0290 (12)	0.0269 (14)
O3	0.0437 (13)	0.0831 (18)	0.1124 (18)	−0.0145 (12)	0.0296 (13)	0.0009 (14)
O4	0.0376 (13)	0.126 (2)	0.120 (2)	0.0027 (14)	0.0169 (13)	0.0300 (18)
O5	0.0558 (16)	0.152 (3)	0.114 (2)	−0.0054 (17)	0.0187 (15)	0.065 (2)
N1	0.0464 (16)	0.096 (2)	0.0650 (16)	0.0006 (15)	0.0193 (13)	0.0115 (15)
N2	0.0301 (13)	0.0731 (18)	0.0675 (16)	0.0000 (11)	0.0173 (12)	0.0058 (13)
N3	0.0347 (14)	0.0673 (19)	0.0693 (16)	−0.0030 (12)	0.0226 (12)	−0.0025 (13)
C1	0.063 (3)	0.113 (3)	0.090 (3)	−0.002 (2)	0.017 (2)	0.034 (2)
C2	0.061 (3)	0.146 (4)	0.099 (3)	0.015 (3)	0.014 (2)	0.035 (3)
C3	0.042 (2)	0.130 (4)	0.079 (2)	0.001 (2)	0.0101 (19)	0.003 (2)
C4	0.0347 (17)	0.097 (3)	0.0587 (19)	−0.0039 (17)	0.0137 (15)	−0.0129 (18)
C5	0.0358 (19)	0.116 (3)	0.086 (2)	−0.015 (2)	0.0189 (18)	−0.018 (2)
C6	0.051 (2)	0.097 (3)	0.102 (3)	−0.026 (2)	0.034 (2)	−0.012 (2)
C7	0.0426 (18)	0.082 (2)	0.082 (2)	−0.0115 (17)	0.0262 (17)	0.0001 (18)
C8	0.0351 (16)	0.072 (2)	0.0551 (18)	−0.0051 (15)	0.0197 (14)	−0.0090 (15)
C9	0.0375 (17)	0.078 (2)	0.0539 (17)	−0.0065 (15)	0.0199 (14)	−0.0074 (16)
C10	0.0399 (17)	0.066 (2)	0.0674 (19)	−0.0008 (15)	0.0222 (15)	0.0061 (16)
C11	0.0386 (17)	0.063 (2)	0.071 (2)	−0.0008 (15)	0.0256 (16)	0.0017 (17)
C12	0.0340 (17)	0.074 (2)	0.069 (2)	0.0005 (15)	0.0151 (15)	0.0062 (17)
C13	0.0381 (17)	0.062 (2)	0.0602 (18)	−0.0018 (14)	0.0167 (14)	−0.0031 (15)
C14	0.0411 (18)	0.070 (2)	0.069 (2)	0.0000 (15)	0.0145 (15)	0.0123 (16)
C15	0.0451 (19)	0.063 (2)	0.070 (2)	−0.0090 (15)	0.0208 (16)	0.0031 (16)
C16	0.0358 (16)	0.057 (2)	0.0625 (18)	−0.0063 (14)	0.0180 (14)	−0.0115 (15)
C17	0.0411 (18)	0.073 (2)	0.078 (2)	0.0042 (16)	0.0203 (16)	0.0082 (18)
C18	0.0443 (18)	0.067 (2)	0.079 (2)	0.0015 (15)	0.0269 (16)	0.0113 (17)
C19	0.044 (2)	0.069 (2)	0.076 (2)	−0.0083 (17)	0.0242 (18)	−0.0094 (19)
C20	0.088 (4)	0.201 (6)	0.163 (5)	0.004 (3)	0.036 (3)	0.073 (4)

Geometric parameters (Å, º) top

O1—C8	1.371 (3)	C6—C7	1.406 (4)
O1—C10	1.425 (3)	C6—H6	0.9300
O2—C11	1.225 (3)	C7—C8	1.357 (4)
O3—C19	1.313 (4)	C7—H7	0.9300
O3—H3	0.8200	C8—C9	1.415 (4)
O4—C19	1.193 (4)	C10—C11	1.503 (4)
O5—C20	1.332 (5)	C10—H10A	0.9700
O5—H5	0.8200	C10—H10B	0.9700
N1—C1	1.318 (4)	C12—C13	1.461 (4)
N1—C9	1.365 (4)	C12—H12	0.9300
N2—C11	1.332 (3)	C13—C14	1.382 (4)
N2—N3	1.379 (3)	C13—C18	1.384 (4)
N2—H2	0.8600	C14—C15	1.378 (4)
N3—C12	1.267 (3)	C14—H14	0.9300
C1—C2	1.390 (5)	C15—C16	1.372 (4)
C1—H1	0.9300	C15—H15	0.9300
C2—C3	1.348 (5)	C16—C17	1.372 (4)
C2—H2A	0.9300	C16—C19	1.486 (4)
C3—C4	1.407 (5)	C17—C18	1.381 (4)
C3—H3A	0.9300	C17—H17	0.9300
C4—C5	1.393 (5)	C18—H18	0.9300
C4—C9	1.413 (4)	C20—H20A	0.9600
C5—C6	1.351 (5)	C20—H20B	0.9600
C5—H5A	0.9300	C20—H20C	0.9600

C8—O1—C10	116.1 (2)	C11—C10—H10A	109.2
C19—O3—H3	109.5	O1—C10—H10B	109.2
C20—O5—H5	109.5	C11—C10—H10B	109.2
C1—N1—C9	117.5 (3)	H10A—C10—H10B	107.9
C11—N2—N3	118.0 (2)	O2—C11—N2	124.6 (3)
C11—N2—H2	121.0	O2—C11—C10	117.6 (3)
N3—N2—H2	121.0	N2—C11—C10	117.8 (3)
C12—N3—N2	116.3 (2)	N3—C12—C13	120.5 (3)
N1—C1—C2	124.9 (4)	N3—C12—H12	119.8
N1—C1—H1	117.6	C13—C12—H12	119.8
C2—C1—H1	117.6	C14—C13—C18	118.5 (3)
C3—C2—C1	118.2 (4)	C14—C13—C12	120.3 (3)
C3—C2—H2A	120.9	C18—C13—C12	121.2 (3)
C1—C2—H2A	120.9	C15—C14—C13	120.9 (3)
C2—C3—C4	120.2 (3)	C15—C14—H14	119.6
C2—C3—H3A	119.9	C13—C14—H14	119.6
C4—C3—H3A	119.9	C16—C15—C14	120.7 (3)
C5—C4—C3	122.7 (3)	C16—C15—H15	119.7
C5—C4—C9	119.5 (3)	C14—C15—H15	119.7
C3—C4—C9	117.8 (3)	C15—C16—C17	118.6 (3)
C6—C5—C4	120.3 (3)	C15—C16—C19	123.4 (3)
C6—C5—H5A	119.9	C17—C16—C19	118.0 (3)
C4—C5—H5A	119.9	C16—C17—C18	121.4 (3)
C5—C6—C7	120.9 (3)	C16—C17—H17	119.3
C5—C6—H6	119.5	C18—C17—H17	119.3
C7—C6—H6	119.5	C17—C18—C13	119.9 (3)
C8—C7—C6	120.5 (3)	C17—C18—H18	120.1
C8—C7—H7	119.8	C13—C18—H18	120.1
C6—C7—H7	119.8	O4—C19—O3	123.5 (3)
C7—C8—O1	124.6 (3)	O4—C19—C16	123.4 (3)
C7—C8—C9	119.7 (3)	O3—C19—C16	113.1 (3)
O1—C8—C9	115.7 (3)	O5—C20—H20A	109.5
N1—C9—C4	121.5 (3)	O5—C20—H20B	109.5
N1—C9—C8	119.3 (3)	H20A—C20—H20B	109.5
C4—C9—C8	119.2 (3)	O5—C20—H20C	109.5
O1—C10—C11	112.0 (2)	H20A—C20—H20C	109.5
O1—C10—H10A	109.2	H20B—C20—H20C	109.5

C11—N2—N3—C12	−176.6 (3)	O1—C8—C9—C4	−179.5 (2)
C9—N1—C1—C2	−0.2 (6)	C8—O1—C10—C11	174.5 (2)
N1—C1—C2—C3	0.0 (7)	N3—N2—C11—O2	1.1 (5)
C1—C2—C3—C4	0.5 (6)	N3—N2—C11—C10	−179.4 (2)
C2—C3—C4—C5	179.6 (4)	O1—C10—C11—O2	−177.3 (3)
C2—C3—C4—C9	−0.9 (6)	O1—C10—C11—N2	3.1 (4)
C3—C4—C5—C6	−179.5 (3)	N2—N3—C12—C13	−179.4 (2)
C9—C4—C5—C6	1.1 (5)	N3—C12—C13—C14	174.4 (3)
C4—C5—C6—C7	−0.8 (5)	N3—C12—C13—C18	−4.9 (5)
C5—C6—C7—C8	0.0 (5)	C18—C13—C14—C15	0.5 (5)
C6—C7—C8—O1	179.7 (3)	C12—C13—C14—C15	−178.9 (3)
C6—C7—C8—C9	0.5 (5)	C13—C14—C15—C16	−1.0 (5)
C10—O1—C8—C7	−0.3 (4)	C14—C15—C16—C17	0.8 (4)
C10—O1—C8—C9	179.0 (2)	C14—C15—C16—C19	−179.0 (3)
C1—N1—C9—C4	−0.1 (5)	C15—C16—C17—C18	−0.1 (5)
C1—N1—C9—C8	−179.4 (3)	C19—C16—C17—C18	179.8 (3)
C5—C4—C9—N1	−179.8 (3)	C16—C17—C18—C13	−0.5 (5)
C3—C4—C9—N1	0.7 (5)	C14—C13—C18—C17	0.3 (5)
C5—C4—C9—C8	−0.5 (4)	C12—C13—C18—C17	179.6 (3)
C3—C4—C9—C8	180.0 (3)	C15—C16—C19—O4	176.7 (3)
C7—C8—C9—N1	179.1 (3)	C17—C16—C19—O4	−3.2 (5)
O1—C8—C9—N1	−0.3 (4)	C15—C16—C19—O3	−3.9 (4)
C7—C8—C9—C4	−0.2 (4)	C17—C16—C19—O3	176.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.82	1.88	2.695 (3)	171
O5—H5···N1	0.82	1.95	2.765 (3)	171
N2—H2···O5	0.86	2.01	2.838 (4)	162

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅N₃O₄·CH₄O
M_r	381.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	10.1166 (18), 11.095 (2), 18.510 (3)
β (°)	115.896 (7)
V (Å³)	1869.0 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.22 × 0.19 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.979, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	9663, 3302, 1666
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.161, 1.02
No. of reflections	3302
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.20

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
O3—H3···O2ⁱ	0.82	1.88	2.695 (3)	171.3
O5—H5···N1	0.82	1.95	2.765 (3)	170.6
N2—H2···O5	0.86	2.01	2.838 (4)	162.0

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

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Chen, C. H. & Shi, J. M. (1998). Coord. Chem. Rev. 171, 161—174. 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 7| July 2009| Page o1601

doi:10.1107/S1600536809021576

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

4-{(E)-N′-[2-(8-Quinolyl­oxy)acetyl]hydrazono­methyl}benzoic acid methanol solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

4-{(E)-N′-[2-(8-Quinolyloxy)acetyl]hydrazonomethyl}benzoic acid methanol solvate