(E)-N′-(4-Bromo­benzyl­idene)-2-(8-quin­ol­yloxy)acetohydrazide mono­hydrate

Tan, J.

doi:10.1107/S1600536809020418

organic compounds

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Volume 65| Part 7| July 2009| Page o1474

doi:10.1107/S1600536809020418

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(E)-N′-(4-Bromobenzylidene)-2-(8-quinolyloxy)acetohydrazide monohydrate

Jun Tan ^a ^*

^aCollege of Biological and Chemical Engineering, Jiaxing University, Jiaxing 314001, People's Republic of China
^*Correspondence e-mail: catalyst007@126.com

(Received 22 May 2009; accepted 28 May 2009; online 6 June 2009)

In the title compound, C₁₈H₁₄BrN₃O₂·H₂O, the dihedral angle between the mean planes of the benzene ring and the quinoline ring system is 34.2 (3)°. In the crystal, the constituents are linked into chains by O—H⋯O, N—H⋯O and O—H⋯N hydrogen bonds.

Related literature

For a related structure, see: Tan (2009 ). For background to the coordination chemistry of 8-hydroxyquinoline and its derivatives, see: Chen & Shi (1998 ); Mona & Wageih (2002 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₈H₁₄BrN₃O₂·H₂O
M_r = 402.25
Monoclinic, C 2/c
a = 21.95 (2) Å
b = 11.841 (8) Å
c = 13.057 (9) Å
β = 93.70 (2)°
V = 3387 (4) Å³
Z = 8
Mo Kα radiation
μ = 2.45 mm⁻¹
T = 295 K
0.20 × 0.18 × 0.15 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Siemens, 1996 ) T_min = 0.640, T_max = 0.710
8378 measured reflections
2988 independent reflections
1334 reflections with I > 2σ(I)
R_int = 0.141

Refinement

R[F² > 2σ(F²)] = 0.070
wR(F²) = 0.178
S = 1.04
2988 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.75 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3	0.86	2.04	2.860 (8)	160
O3—H19⋯N1	0.85	1.97	2.806 (8)	170
O3—H20⋯O2ⁱ	0.85	2.11	2.783 (7)	136
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536809020418/hb2981sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809020418/hb2981Isup2.hkl

checkCIF report

Comment top

8-Hydroxyquinoline and its derivatives constitute well known ligands in coordination chemistry (Chen & Shi, 1998; Mona & Wageih, 2002). 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 (Allen et al., 1987), and are comparable to those in the related compound (E)-N'-[1-(4-Hydroxyphenyl)ethylidene]-2-(quinolin-8- yloxy)acetohydrazide methanol solvate (Tan, 2009). The mean planes of the benzene ring and the quinoline rings make a dihedral angle of 34.2 (3)°. In the crystal structure, the C₁₈H₁₄BrN₃O₂ molecules and the water molecules are linked into chains by O—H···O, N—H···O and O—H···N hydrogen bonds.

Related literature top

For a related structure, see: Tan (2009). For background to the coordination chemistry of 8-hydroxyquinoline and its derivatives, see: Chen & Shi (1998); Mona & Wageih (2002). For reference structural data, see: Allen et al. (1987).

Experimental top

2-(quinolin-8-yloxy)acetohydrazide (2.18 g, 10 mmol), 4-bromobenzaldehyde (1.85 g, 10 mmol), ethanol (40 ml) and some drops of acetic acid were added to a 100 ml flask, and refluxed for 5 h. After cooling to room temperature, the mixture was filtered. Colourless blocks of (I) were obtained by slow evaporation of a acetone-methanol (1:2, v/v) solution over a period of 3 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.
	Fig. 2. The structure of the chains formed via hydrogen bonds, H atoms have been omitted for clarity. The dashed lines indicate hydrogen bonds.

(E)-N'-(4-Bromobenzylidene)-2-(8-quinolyloxy)acetohydrazide monohydrate top

Crystal data top

C₁₈H₁₄BrN₃O₂·H₂O	F(000) = 1632
M_r = 402.25	D_x = 1.578 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1037 reflections
a = 21.95 (2) Å	θ = 2.5–19.7°
b = 11.841 (8) Å	µ = 2.45 mm⁻¹
c = 13.057 (9) Å	T = 295 K
β = 93.70 (2)°	Block, colourless
V = 3387 (4) Å³	0.20 × 0.18 × 0.15 mm
Z = 8

Data collection top

Siemens SMART CCD area-detector diffractometer	2988 independent reflections
Radiation source: fine-focus sealed tube	1334 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.141
ω scans	θ_max = 25.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −15→26
T_min = 0.640, T_max = 0.710	k = −14→13
8378 measured reflections	l = −15→15

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)] = 0.070	H-atom parameters constrained
wR(F²) = 0.178	w = 1/[σ²(F_o²) + (0.0524P)² + 0.013P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2988 reflections	Δρ_max = 0.52 e Å⁻³
227 parameters	Δρ_min = −0.75 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: 0.0009 (2)

Crystal data top

C₁₈H₁₄BrN₃O₂·H₂O	V = 3387 (4) Å³
M_r = 402.25	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 21.95 (2) Å	µ = 2.45 mm⁻¹
b = 11.841 (8) Å	T = 295 K
c = 13.057 (9) Å	0.20 × 0.18 × 0.15 mm
β = 93.70 (2)°

Data collection top

Siemens SMART CCD area-detector diffractometer	2988 independent reflections
Absorption correction: multi-scan (SADABS; Siemens, 1996)	1334 reflections with I > 2σ(I)
T_min = 0.640, T_max = 0.710	R_int = 0.141
8378 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	0 restraints
wR(F²) = 0.178	H-atom parameters constrained
S = 1.04	Δρ_max = 0.52 e Å⁻³
2988 reflections	Δρ_min = −0.75 e Å⁻³
227 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
Br1	0.90959 (4)	−0.09454 (8)	−0.24581 (7)	0.0744 (4)
O1	0.6370 (2)	0.0076 (4)	0.4059 (4)	0.0572 (15)
O2	0.7206 (2)	−0.2340 (5)	0.3387 (4)	0.0720 (18)
O3	0.6745 (2)	0.1677 (4)	0.2304 (4)	0.0709 (17)
H19	0.6501	0.1798	0.2773	0.106*
H20	0.7041	0.2133	0.2416	0.106*
N1	0.5826 (3)	0.2041 (6)	0.3665 (5)	0.0569 (18)
N2	0.7139 (2)	−0.0597 (5)	0.2679 (5)	0.0512 (17)
H2	0.7015	0.0089	0.2724	0.061*
N3	0.7481 (2)	−0.0944 (5)	0.1878 (4)	0.0498 (16)
C1	0.5556 (4)	0.3013 (8)	0.3491 (7)	0.071 (2)
H1	0.5638	0.3395	0.2893	0.085*
C2	0.5152 (4)	0.3521 (7)	0.4142 (7)	0.071 (3)
H2A	0.4977	0.4219	0.3980	0.085*
C3	0.5024 (3)	0.2977 (8)	0.5002 (7)	0.069 (3)
H3	0.4749	0.3292	0.5432	0.083*
C4	0.5300 (3)	0.1940 (6)	0.5264 (6)	0.0469 (19)
C5	0.5217 (4)	0.1349 (7)	0.6158 (6)	0.060 (2)
H5	0.4951	0.1631	0.6621	0.072*
C6	0.5512 (4)	0.0379 (8)	0.6369 (7)	0.067 (2)
H6	0.5448	0.0005	0.6979	0.081*
C7	0.5913 (3)	−0.0086 (7)	0.5699 (6)	0.060 (2)
H7	0.6115	−0.0760	0.5860	0.072*
C8	0.6007 (3)	0.0465 (6)	0.4799 (6)	0.0462 (19)
C9	0.5708 (3)	0.1502 (6)	0.4560 (6)	0.0459 (19)
C10	0.6614 (3)	−0.1020 (6)	0.4229 (6)	0.054 (2)
H10A	0.6283	−0.1556	0.4271	0.065*
H10B	0.6855	−0.1032	0.4879	0.065*
C11	0.7011 (3)	−0.1375 (7)	0.3383 (6)	0.053 (2)
C12	0.7666 (3)	−0.0121 (7)	0.1327 (6)	0.050 (2)
H12	0.7585	0.0621	0.1509	0.060*
C13	0.8002 (3)	−0.0349 (7)	0.0416 (5)	0.0441 (19)
C14	0.8235 (3)	0.0555 (6)	−0.0099 (6)	0.051 (2)
H14	0.8178	0.1285	0.0139	0.061*
C15	0.8551 (3)	0.0384 (7)	−0.0965 (6)	0.058 (2)
H15	0.8714	0.0993	−0.1304	0.069*
C16	0.8623 (3)	−0.0703 (7)	−0.1320 (6)	0.050 (2)
C17	0.8391 (3)	−0.1611 (7)	−0.0827 (6)	0.050 (2)
H17	0.8437	−0.2340	−0.1073	0.060*
C18	0.8085 (3)	−0.1412 (6)	0.0047 (5)	0.0459 (19)
H18	0.7932	−0.2023	0.0397	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0833 (7)	0.0776 (7)	0.0666 (6)	0.0062 (5)	0.0376 (5)	0.0007 (6)
O1	0.075 (4)	0.046 (3)	0.055 (3)	0.009 (3)	0.036 (3)	0.003 (3)
O2	0.096 (4)	0.037 (3)	0.089 (5)	0.008 (3)	0.056 (4)	0.004 (3)
O3	0.078 (4)	0.055 (4)	0.086 (4)	−0.008 (3)	0.050 (3)	−0.008 (3)
N1	0.060 (4)	0.048 (4)	0.066 (5)	0.004 (3)	0.025 (4)	−0.004 (4)
N2	0.053 (4)	0.041 (4)	0.063 (4)	0.001 (3)	0.033 (3)	−0.002 (3)
N3	0.053 (4)	0.045 (4)	0.055 (4)	−0.001 (3)	0.031 (3)	−0.007 (4)
C1	0.081 (6)	0.069 (7)	0.066 (6)	0.005 (5)	0.027 (5)	0.015 (5)
C2	0.076 (6)	0.059 (6)	0.080 (7)	0.027 (5)	0.023 (5)	0.004 (5)
C3	0.056 (6)	0.077 (7)	0.077 (7)	0.004 (5)	0.027 (5)	−0.014 (6)
C4	0.047 (5)	0.046 (5)	0.050 (5)	−0.001 (4)	0.024 (4)	−0.002 (4)
C5	0.069 (6)	0.064 (6)	0.051 (5)	−0.005 (5)	0.028 (4)	−0.011 (5)
C6	0.069 (6)	0.071 (7)	0.066 (6)	−0.004 (5)	0.037 (5)	0.007 (5)
C7	0.063 (5)	0.053 (5)	0.068 (6)	0.003 (4)	0.036 (5)	0.005 (5)
C8	0.053 (5)	0.044 (5)	0.045 (5)	−0.003 (4)	0.024 (4)	−0.004 (4)
C9	0.045 (5)	0.046 (5)	0.049 (5)	−0.003 (4)	0.016 (4)	−0.004 (4)
C10	0.064 (5)	0.044 (5)	0.058 (5)	−0.001 (4)	0.033 (4)	0.003 (4)
C11	0.053 (5)	0.046 (5)	0.062 (5)	−0.012 (4)	0.021 (4)	−0.008 (5)
C12	0.049 (5)	0.044 (5)	0.061 (5)	0.001 (4)	0.025 (4)	−0.004 (4)
C13	0.038 (4)	0.050 (5)	0.047 (5)	0.000 (4)	0.019 (4)	0.003 (4)
C14	0.052 (5)	0.040 (5)	0.063 (5)	0.002 (4)	0.023 (4)	−0.006 (4)
C15	0.055 (5)	0.049 (5)	0.072 (6)	0.000 (4)	0.027 (4)	0.015 (5)
C16	0.044 (4)	0.052 (6)	0.058 (5)	0.008 (4)	0.016 (4)	0.007 (4)
C17	0.054 (5)	0.049 (5)	0.047 (5)	0.003 (4)	0.013 (4)	−0.009 (4)
C18	0.053 (5)	0.041 (5)	0.045 (5)	−0.005 (4)	0.019 (4)	0.001 (4)

Geometric parameters (Å, º) top

Br1—C16	1.889 (7)	C5—H5	0.9300
O1—C8	1.371 (7)	C6—C7	1.394 (9)
O1—C10	1.417 (8)	C6—H6	0.9300
O2—C11	1.220 (8)	C7—C8	1.371 (10)
O3—H19	0.8500	C7—H7	0.9300
O3—H20	0.8500	C8—C9	1.417 (10)
N1—C1	1.309 (9)	C10—C11	1.509 (9)
N1—C9	1.370 (9)	C10—H10A	0.9700
N2—C11	1.344 (9)	C10—H10B	0.9700
N2—N3	1.389 (7)	C12—C13	1.464 (9)
N2—H2	0.8600	C12—H12	0.9300
N3—C12	1.292 (8)	C13—C18	1.364 (9)
C1—C2	1.402 (11)	C13—C14	1.381 (9)
C1—H1	0.9300	C14—C15	1.379 (9)
C2—C3	1.341 (11)	C14—H14	0.9300
C2—H2A	0.9300	C15—C16	1.380 (10)
C3—C4	1.402 (10)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.368 (10)
C4—C5	1.383 (10)	C17—C18	1.380 (9)
C4—C9	1.422 (9)	C17—H17	0.9300
C5—C6	1.338 (10)	C18—H18	0.9300

C8—O1—C10	115.4 (5)	N1—C9—C4	122.9 (7)
H19—O3—H20	106.1	C8—C9—C4	118.3 (7)
C1—N1—C9	116.7 (7)	O1—C10—C11	111.8 (6)
C11—N2—N3	117.4 (6)	O1—C10—H10A	109.3
C11—N2—H2	121.3	C11—C10—H10A	109.3
N3—N2—H2	121.3	O1—C10—H10B	109.3
C12—N3—N2	113.6 (6)	C11—C10—H10B	109.3
N1—C1—C2	124.7 (8)	H10A—C10—H10B	107.9
N1—C1—H1	117.7	O2—C11—N2	123.8 (7)
C2—C1—H1	117.7	O2—C11—C10	118.4 (7)
C3—C2—C1	118.5 (8)	N2—C11—C10	117.8 (7)
C3—C2—H2A	120.8	N3—C12—C13	120.4 (7)
C1—C2—H2A	120.8	N3—C12—H12	119.8
C2—C3—C4	121.0 (8)	C13—C12—H12	119.8
C2—C3—H3	119.5	C18—C13—C14	118.7 (6)
C4—C3—H3	119.5	C18—C13—C12	122.9 (7)
C5—C4—C3	124.8 (7)	C14—C13—C12	118.3 (7)
C5—C4—C9	119.0 (7)	C15—C14—C13	120.5 (7)
C3—C4—C9	116.2 (7)	C15—C14—H14	119.7
C6—C5—C4	121.3 (7)	C13—C14—H14	119.7
C6—C5—H5	119.3	C14—C15—C16	119.1 (7)
C4—C5—H5	119.3	C14—C15—H15	120.4
C5—C6—C7	121.7 (8)	C16—C15—H15	120.4
C5—C6—H6	119.1	C17—C16—C15	121.4 (7)
C7—C6—H6	119.1	C17—C16—Br1	119.4 (6)
C8—C7—C6	119.1 (7)	C15—C16—Br1	119.1 (6)
C8—C7—H7	120.5	C16—C17—C18	118.1 (7)
C6—C7—H7	120.5	C16—C17—H17	121.0
C7—C8—O1	124.8 (7)	C18—C17—H17	121.0
C7—C8—C9	120.6 (7)	C13—C18—C17	122.2 (7)
O1—C8—C9	114.7 (6)	C13—C18—H18	118.9
N1—C9—C8	118.7 (6)	C17—C18—H18	118.9

C11—N2—N3—C12	−169.8 (7)	C3—C4—C9—N1	−0.8 (11)
C9—N1—C1—C2	−1.2 (13)	C5—C4—C9—C8	0.8 (11)
N1—C1—C2—C3	−0.6 (14)	C3—C4—C9—C8	178.9 (7)
C1—C2—C3—C4	1.8 (14)	C8—O1—C10—C11	−179.5 (6)
C2—C3—C4—C5	176.9 (8)	N3—N2—C11—O2	4.4 (12)
C2—C3—C4—C9	−1.1 (12)	N3—N2—C11—C10	−177.2 (6)
C3—C4—C5—C6	−177.9 (8)	O1—C10—C11—O2	−173.5 (7)
C9—C4—C5—C6	0.1 (12)	O1—C10—C11—N2	7.9 (10)
C4—C5—C6—C7	−0.4 (13)	N2—N3—C12—C13	−176.4 (6)
C5—C6—C7—C8	−0.1 (13)	N3—C12—C13—C18	6.5 (11)
C6—C7—C8—O1	−177.3 (7)	N3—C12—C13—C14	−174.6 (7)
C6—C7—C8—C9	1.0 (12)	C18—C13—C14—C15	−0.6 (11)
C10—O1—C8—C7	5.5 (11)	C12—C13—C14—C15	−179.6 (7)
C10—O1—C8—C9	−172.9 (6)	C13—C14—C15—C16	1.1 (12)
C1—N1—C9—C8	−177.8 (7)	C14—C15—C16—C17	−0.5 (11)
C1—N1—C9—C4	1.9 (11)	C14—C15—C16—Br1	−176.4 (6)
C7—C8—C9—N1	178.3 (7)	C15—C16—C17—C18	−0.6 (11)
O1—C8—C9—N1	−3.2 (10)	Br1—C16—C17—C18	175.3 (5)
C7—C8—C9—C4	−1.4 (11)	C14—C13—C18—C17	−0.6 (11)
O1—C8—C9—C4	177.1 (7)	C12—C13—C18—C17	178.4 (7)
C5—C4—C9—N1	−178.9 (7)	C16—C17—C18—C13	1.1 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.86	2.04	2.860 (8)	160
O3—H19···N1	0.85	1.97	2.806 (8)	170
O3—H20···O2ⁱ	0.85	2.11	2.783 (7)	136

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄BrN₃O₂·H₂O
M_r	402.25
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	295
a, b, c (Å)	21.95 (2), 11.841 (8), 13.057 (9)
β (°)	93.70 (2)
V (Å³)	3387 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.45
Crystal size (mm)	0.20 × 0.18 × 0.15

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Siemens, 1996)
T_min, T_max	0.640, 0.710
No. of measured, independent and observed [I > 2σ(I)] reflections	8378, 2988, 1334
R_int	0.141
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.178, 1.04
No. of reflections	2988
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.75

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
N2—H2···O3	0.86	2.04	2.860 (8)	160
O3—H19···N1	0.85	1.97	2.806 (8)	170
O3—H20···O2ⁱ	0.85	2.11	2.783 (7)	136

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

Acknowledgements

This project was supported by the Natural Science Foundation of Zhejiang Province for Distinguished Young Students (No. 2008R40G2190024) and the Scientific Research Fund of the Zhejiang Provincial Education Department (No. Y200803569).

References

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