N′-(2-Hydroxy­benzyl­idene)-2-(quinolin-8-yl­oxy)acetohydrazide monohydrate

In the title compound, C₁₈H₁₅N₃O₃·H₂O, the dihedral angle between the planes of the benzene ring and the quinoline ring system is 26.6 (2)°. Each solvent water mol­ecule is linked to two acetohydrazide mol­ecules via inter­molecular N—H...O, O—H...N and O—H...O hydrogen bonds, forming chains along [010].

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.063
• wR factor = 0.142
• Data-to-parameter ratio = 8.2

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.116
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2
PLAT731_ALERT_1_C Bond    Calc     0.84(4), Rep   0.841(10) ......       4.00 su-Rat
              O1W  -H2W1    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.84(4), Rep   0.836(10) ......       4.00 su-Rat
              O1W  -H1W1    1.555   1.555

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.01
           From the CIF: _reflns_number_total               1924
           Count of symmetry unique reflns         1925
           Completeness (_total/calc)             99.95%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

N'-(2-Hydroxybenzylidene)-2-(quinolin-8-yloxy)acetohydrazide monohydrate

Crystal data

C18H15N3O3·H2O	F(000) = 712
Mr = 339.35	Dx = 1.371 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1233 reflections
a = 4.6661 (12) Å	θ = 2.7–20.9°
b = 15.110 (4) Å	µ = 0.10 mm^−1
c = 23.314 (6) Å	T = 293 K
V = 1643.7 (7) Å^3	Plate, colourless
Z = 4	0.43 × 0.11 × 0.09 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	1924 independent reflections
Radiation source: fine-focus sealed tube	1317 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.116
Detector resolution: 8.33 pixels mm^-1	θmax = 26.0°, θmin = 1.6°
ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −18→18
Tmin = 0.959, Tmax = 0.991	l = −19→28
9129 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0499P)^2 + 0.0947P] where P = (Fo^2 + 2Fc^2)/3
1924 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.15 e Å^−3
3 restraints	Δρmin = −0.16 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.3629 (7)	0.42857 (17)	0.17480 (12)	0.0556 (8)
O2	−0.0655 (9)	0.57718 (18)	0.25640 (15)	0.0818 (11)
O3	−0.5015 (9)	0.4943 (2)	0.38917 (13)	0.0826 (11)
H3	−0.3872	0.4931	0.3625	0.124*
N1	0.5978 (9)	0.2706 (2)	0.15235 (14)	0.0575 (10)
N2	−0.0330 (8)	0.4279 (2)	0.25852 (14)	0.0533 (9)
H2	0.0411	0.3804	0.2445	0.064*
N3	−0.2297 (8)	0.4245 (2)	0.30244 (14)	0.0559 (9)
C1	0.7155 (13)	0.1933 (3)	0.1413 (2)	0.0738 (16)
H1	0.6602	0.1451	0.1635	0.089*
C2	0.9184 (13)	0.1794 (3)	0.0983 (2)	0.0753 (15)
H2A	0.9990	0.1238	0.0928	0.090*
C3	0.9954 (12)	0.2479 (4)	0.0648 (2)	0.0758 (15)
H3A	1.1294	0.2395	0.0358	0.091*
C4	0.8738 (11)	0.3326 (3)	0.07346 (18)	0.0589 (12)
C5	0.9389 (11)	0.4074 (3)	0.03877 (19)	0.0725 (15)
H5	1.0658	0.4021	0.0082	0.087*
C6	0.8139 (11)	0.4868 (3)	0.0506 (2)	0.0713 (14)
H6	0.8583	0.5356	0.0280	0.086*
C7	0.6210 (10)	0.4969 (3)	0.09589 (18)	0.0620 (12)
H7	0.5393	0.5520	0.1030	0.074*
C8	0.5510 (10)	0.4262 (3)	0.12995 (17)	0.0509 (11)
C9	0.6748 (10)	0.3413 (3)	0.11871 (16)	0.0510 (11)
C10	0.2552 (10)	0.5132 (3)	0.19118 (17)	0.0564 (12)
H10A	0.1684	0.5412	0.1580	0.068*
H10B	0.4140	0.5500	0.2035	0.068*
C11	0.0393 (10)	0.5088 (3)	0.23826 (18)	0.0553 (11)
C12	−0.3317 (10)	0.3488 (3)	0.31575 (16)	0.0523 (11)
H12	−0.2740	0.2987	0.2956	0.063*
C13	−0.5382 (10)	0.3404 (3)	0.36241 (16)	0.0509 (11)
C14	−0.6144 (10)	0.4119 (3)	0.39707 (18)	0.0581 (12)
C15	−0.8104 (12)	0.4016 (3)	0.44068 (19)	0.0704 (14)
H15	−0.8613	0.4497	0.4634	0.084*
C16	−0.9320 (12)	0.3192 (4)	0.4508 (2)	0.0759 (15)
H16	−1.0598	0.3120	0.4810	0.091*
C17	−0.8655 (11)	0.2481 (4)	0.4165 (2)	0.0723 (14)
H17	−0.9537	0.1936	0.4224	0.087*
C18	−0.6664 (11)	0.2585 (3)	0.37338 (18)	0.0622 (12)
H18	−0.6161	0.2099	0.3510	0.075*
O1W	0.1903 (9)	0.2598 (2)	0.23755 (15)	0.0698 (10)
H2W1	0.314 (9)	0.262 (3)	0.2114 (18)	0.11 (2)*
H1W1	0.124 (14)	0.2086 (19)	0.240 (3)	0.17 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.060 (2)	0.0431 (15)	0.0639 (18)	0.0017 (16)	0.0106 (17)	0.0010 (14)
O2	0.093 (3)	0.0429 (16)	0.109 (3)	0.0063 (19)	0.029 (2)	−0.0135 (18)
O3	0.088 (3)	0.063 (2)	0.097 (3)	−0.008 (2)	0.022 (2)	−0.0190 (19)
N1	0.061 (3)	0.051 (2)	0.060 (2)	0.000 (2)	−0.0088 (19)	0.0010 (18)
N2	0.053 (2)	0.0479 (19)	0.059 (2)	0.003 (2)	0.0060 (19)	−0.0072 (17)
N3	0.054 (2)	0.054 (2)	0.059 (2)	0.000 (2)	0.007 (2)	−0.0060 (18)
C1	0.092 (4)	0.060 (3)	0.070 (3)	0.010 (3)	−0.015 (3)	−0.011 (3)
C2	0.081 (4)	0.068 (3)	0.077 (3)	0.023 (3)	−0.010 (3)	−0.023 (3)
C3	0.067 (3)	0.093 (4)	0.068 (3)	0.007 (3)	−0.005 (3)	−0.027 (3)
C4	0.052 (3)	0.073 (3)	0.051 (2)	−0.005 (3)	−0.007 (2)	−0.015 (2)
C5	0.065 (3)	0.095 (4)	0.057 (3)	−0.007 (3)	0.012 (3)	−0.009 (3)
C6	0.073 (4)	0.074 (3)	0.067 (3)	−0.019 (3)	0.011 (3)	0.006 (3)
C7	0.061 (3)	0.062 (3)	0.062 (3)	−0.003 (3)	−0.001 (2)	0.007 (2)
C8	0.046 (3)	0.057 (3)	0.050 (2)	0.000 (2)	−0.003 (2)	−0.002 (2)
C9	0.048 (3)	0.057 (3)	0.048 (2)	−0.002 (2)	−0.006 (2)	−0.007 (2)
C10	0.053 (3)	0.045 (2)	0.071 (3)	0.001 (2)	0.002 (2)	−0.002 (2)
C11	0.054 (3)	0.048 (3)	0.063 (3)	−0.003 (2)	−0.001 (2)	−0.004 (2)
C12	0.049 (3)	0.053 (3)	0.054 (3)	0.002 (2)	0.001 (2)	−0.006 (2)
C13	0.045 (3)	0.059 (3)	0.048 (2)	0.001 (2)	−0.010 (2)	0.003 (2)
C14	0.051 (3)	0.065 (3)	0.058 (3)	0.005 (3)	−0.005 (2)	−0.003 (2)
C15	0.065 (3)	0.091 (4)	0.055 (3)	0.012 (3)	0.006 (3)	−0.003 (3)
C16	0.060 (3)	0.109 (4)	0.059 (3)	0.001 (4)	0.007 (3)	0.026 (3)
C17	0.066 (3)	0.080 (3)	0.071 (3)	0.000 (3)	0.005 (3)	0.024 (3)
C18	0.063 (3)	0.059 (3)	0.065 (3)	−0.001 (3)	−0.001 (3)	0.011 (2)
O1W	0.089 (3)	0.0472 (18)	0.073 (2)	−0.0122 (19)	0.019 (2)	−0.0098 (16)

Geometric parameters (Å, º)

O1—C8	1.366 (5)	C6—H6	0.93
O1—C10	1.426 (5)	C7—C8	1.370 (5)
O2—C11	1.219 (5)	C7—H7	0.93
O3—C14	1.364 (5)	C8—C9	1.431 (5)
O3—H3	0.82	C10—C11	1.491 (6)
N1—C1	1.316 (5)	C10—H10A	0.97
N1—C9	1.373 (5)	C10—H10B	0.97
N2—C11	1.354 (5)	C12—C13	1.459 (6)
N2—N3	1.376 (5)	C12—H12	0.93
N2—H2	0.86	C13—C14	1.395 (6)
N3—C12	1.278 (5)	C13—C18	1.398 (6)
C1—C2	1.395 (7)	C14—C15	1.376 (6)
C1—H1	0.93	C15—C16	1.388 (6)
C2—C3	1.344 (6)	C15—H15	0.93
C2—H2A	0.93	C16—C17	1.374 (6)
C3—C4	1.415 (6)	C16—H16	0.93
C3—H3A	0.93	C17—C18	1.378 (6)
C4—C9	1.411 (6)	C17—H17	0.93
C4—C5	1.422 (6)	C18—H18	0.93
C5—C6	1.363 (6)	O1W—H2W1	0.841 (10)
C5—H5	0.93	O1W—H1W1	0.836 (10)
C6—C7	1.395 (6)
C8—O1—C10	117.1 (3)	C4—C9—C8	119.1 (4)
C14—O3—H3	109.5	O1—C10—C11	113.3 (3)
C1—N1—C9	118.0 (4)	O1—C10—H10A	108.9
C11—N2—N3	117.3 (3)	C11—C10—H10A	108.9
C11—N2—H2	121.3	O1—C10—H10B	108.9
N3—N2—H2	121.3	C11—C10—H10B	108.9
C12—N3—N2	117.5 (3)	H10A—C10—H10B	107.7
N1—C1—C2	123.8 (5)	O2—C11—N2	123.0 (4)
N1—C1—H1	118.1	O2—C11—C10	119.2 (4)
C2—C1—H1	118.1	N2—C11—C10	117.7 (4)
C3—C2—C1	118.9 (5)	N3—C12—C13	120.3 (4)
C3—C2—H2A	120.5	N3—C12—H12	119.9
C1—C2—H2A	120.5	C13—C12—H12	119.9
C2—C3—C4	120.4 (5)	C14—C13—C18	118.1 (4)
C2—C3—H3A	119.8	C14—C13—C12	122.2 (4)
C4—C3—H3A	119.8	C18—C13—C12	119.7 (4)
C9—C4—C3	117.0 (4)	O3—C14—C15	117.4 (4)
C9—C4—C5	119.4 (4)	O3—C14—C13	122.0 (4)
C3—C4—C5	123.5 (5)	C15—C14—C13	120.6 (5)
C6—C5—C4	119.5 (4)	C14—C15—C16	119.9 (5)
C6—C5—H5	120.2	C14—C15—H15	120.1
C4—C5—H5	120.2	C16—C15—H15	120.1
C5—C6—C7	121.7 (5)	C17—C16—C15	120.7 (4)
C5—C6—H6	119.1	C17—C16—H16	119.7
C7—C6—H6	119.1	C15—C16—H16	119.7
C8—C7—C6	120.5 (4)	C16—C17—C18	119.2 (5)
C8—C7—H7	119.8	C16—C17—H17	120.4
C6—C7—H7	119.8	C18—C17—H17	120.4
O1—C8—C7	125.2 (4)	C17—C18—C13	121.5 (5)
O1—C8—C9	115.0 (4)	C17—C18—H18	119.2
C7—C8—C9	119.8 (4)	C13—C18—H18	119.2
N1—C9—C4	121.8 (4)	H2W1—O1W—H1W1	110 (3)
N1—C9—C8	119.2 (4)
C11—N2—N3—C12	169.5 (4)	O1—C8—C9—C4	−179.4 (4)
C9—N1—C1—C2	1.4 (7)	C7—C8—C9—C4	1.7 (6)
N1—C1—C2—C3	−1.7 (8)	C8—O1—C10—C11	176.8 (3)
C1—C2—C3—C4	0.4 (8)	N3—N2—C11—O2	−1.4 (7)
C2—C3—C4—C9	0.9 (7)	N3—N2—C11—C10	179.2 (4)
C2—C3—C4—C5	−178.2 (5)	O1—C10—C11—O2	179.1 (4)
C9—C4—C5—C6	1.7 (7)	O1—C10—C11—N2	−1.5 (6)
C3—C4—C5—C6	−179.3 (5)	N2—N3—C12—C13	179.2 (3)
C4—C5—C6—C7	−0.5 (7)	N3—C12—C13—C14	−5.4 (6)
C5—C6—C7—C8	−0.1 (7)	N3—C12—C13—C18	174.6 (4)
C10—O1—C8—C7	−7.2 (6)	C18—C13—C14—O3	−179.6 (4)
C10—O1—C8—C9	174.1 (4)	C12—C13—C14—O3	0.4 (6)
C6—C7—C8—O1	−179.2 (4)	C18—C13—C14—C15	−0.1 (6)
C6—C7—C8—C9	−0.5 (6)	C12—C13—C14—C15	179.9 (4)
C1—N1—C9—C4	0.0 (6)	O3—C14—C15—C16	−179.9 (5)
C1—N1—C9—C8	−179.7 (4)	C13—C14—C15—C16	0.6 (7)
C3—C4—C9—N1	−1.1 (6)	C14—C15—C16—C17	−2.0 (7)
C5—C4—C9—N1	178.0 (4)	C15—C16—C17—C18	2.8 (8)
C3—C4—C9—C8	178.6 (4)	C16—C17—C18—C13	−2.3 (7)
C5—C4—C9—C8	−2.3 (6)	C14—C13—C18—C17	0.9 (7)
O1—C8—C9—N1	0.3 (5)	C12—C13—C18—C17	−179.1 (4)
C7—C8—C9—N1	−178.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N3	0.82	1.89	2.610 (5)	146
N2—H2···O1	0.86	2.33	2.687 (5)	105
N2—H2···O1W	0.86	1.96	2.789 (5)	162
O1W—H1W1···O2^i	0.84 (4)	2.01 (3)	2.824 (4)	166 (6)
O1W—H2W1···N1	0.84 (4)	1.91 (4)	2.755 (5)	178 (4)

Symmetry code: (i) −x, y−1/2, −z+1/2.