(E)-N'-(4-Bromo-benzyl-idene)-2-(8-quin-ol-yloxy)acetohydrazide mono-hydrate.

In the title compound, C(18)H(14)BrN(3)O(2)·H(2)O, 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 = 402.25

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.178

S = 1.04

2988 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.75 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/S1600536809020418/hb2981sup1.cif

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

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

C18H14BrN3O2·H2O	F(000) = 1632
Mr = 402.25	Dx = 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

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

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(Fo2) + (0.0524P)2 + 0.013P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2988 reflections	Δρmax = 0.52 e Å−3
227 parameters	Δρmin = −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)

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
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*

	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)

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)

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

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) .