(E)-N′-(4-Hydroxy­benzyl­idene)-4-(quino­lin-8-yl­oxy)butanohydrazide hemi­hydrate

In the title compound, C₂₀H₁₉N₃O₃·0.5H₂O, the mean planes of the benzene ring and quinoline group make a dihedral angle of 98.6 (3)°. The mol­ecules are connected via inter­molecular N—H...O and O—H...N hydrogen bonds into infinite chains. The chains are linked by the water mol­ecule through O—H...O hydrogen bonds (the water mol­ecules are located on crystallographic twofold rotation axes).

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.061
• wR factor = 0.187
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level A
CHEMW01_ALERT_1_A  The ratio of given/expected molecular weight as calculated
            from the _chemical_formula_sum lies outside
            the range 0.90 <> 1.10
            Calculated formula weight =   716.7920
            Formula weight given      =   358.3900
CHEMW03_ALERT_2_A ALERT: The ratio of given/expected molecular weight as
            calculated from the _atom_site* data lies outside
            the range 0.90 <> 1.10
           From the CIF: _cell_formula_units_Z                    4
           From the CIF: _chemical_formula_weight           358.39
           TEST: Calculate formula weight from _atom_site_*
           atom     mass    num     sum
           C        12.01   40.00  480.44
           H         1.01   40.00   40.32
           N        14.01    6.00   84.04
           O        16.00    7.00  111.99
           Calculated formula weight              716.79
DENSD01_ALERT_1_A  The ratio of the submitted crystal density and that
            calculated from the formula is outside the range 0.90 <> 1.10
            Crystal density given    =      1.346
            Calculated crystal density =      0.673
PLAT043_ALERT_1_A Check Reported Molecular Weight ................     358.39
PLAT046_ALERT_1_A Reported Z, MW and D(calc) are Inconsistent ....       0.67

Alert level C
CHEMW01_ALERT_1_C  The difference between the given and expected weight for
            compound is greater 1 mass unit. Check that all hydrogen
            atoms have been taken into account.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C40 H40 N6 O7
            Atom count from _chemical_formula_moiety:C20 H20 N3 O3.5

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

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

---

S1. Comment

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. The bond lengths and angles in (I) fall within their expected ranges (Allen et al., 1987). The conformation along the C7—N1—N2—C8—C9—C10—C11—O3 bond sequence is trans-(-)gauche-trans-trans-(+)gauche (Fig.1). The mean planes of the benzene ring and quinoline group make a dihedral angle of 98.6 (3)°. In the crystal structure (Table and Fig. 2), intermolecular N—H···O and O—H···N hydrogen bonds into infinite chains. The chains was linked by the water molecular through O—H···O hydrogen bonds (H₂O molecules located on 2 axes).

Related literature

For related literature, see: Allen et al. (1987); Chen & Shi (1998); Mona & Wageih (2002).

S2. Experimental

4–(Quinolin–8–yl–oxy)butanohydrazide (0.01 mol), 4–hydroxybenzaldehyde (0.01 mol), ethanol (60 ml) and some drops of acetic acid were added to a 100 ml flask and refluxed for 6 h. After cooling to room temperature, the solid product was separated by filtration. Colourless single crystals suitable for X–ray diffraction study were obtained by slow evaporation of a N,N-dimethylformamide solution over a period of two weeks (m.p. 521 K). Calculated for C₄₀H₄₀N₆O₇: C 67.02, H 5.63, N 11.72%; found: C 66.98, H 5.58, N 11.77%.

S3. Refinement

All H atoms were placed in idealized positions (C—H = 0.93–0.97 Å, O—H = 0.82–0.85 Å, N—H = 0.86 Å) and refined as riding atoms. For those bound to C, U_iso(H) = 1.2U_eq(C,N) or 1.5U_eq(O).

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The molecular structure of (I) with the atoms numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are drawn as spheres with arbitrary radius.
	Fig. 2. Detail of (I) showing part of a hydrogen–bonded chain. H atoms and hydrate have been omitted for clarity and the dashed lines represent the O···N contacts of the hydrogen bonds.

(E)-N'-(4-Hydroxybenzylidene)-4-(quinolin-8-yloxy)butanohydrazide hemihydrate

Crystal data

C20H19N3O3·0.5H2O	F(000) = 1512
Mr = 358.39	Dx = 1.346 Mg m^−3 Dm = 1.346 Mg m^−3 Dm measured by not measured
Monoclinic, C2/c	Melting point: 521 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 29.905 (3) Å	Cell parameters from 1208 reflections
b = 10.4609 (9) Å	θ = 2.1–18.7°
c = 11.4613 (10) Å	µ = 0.09 mm^−1
β = 99.507 (4)°	T = 295 K
V = 3536.2 (6) Å^3	Block, colorless
Z = 8	0.28 × 0.26 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3117 independent reflections
Radiation source: fine–focus sealed tube	1697 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.094
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −34→35
Tmin = 0.974, Tmax = 0.979	k = −12→12
15979 measured reflections	l = −13→13

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.061	H-atom parameters constrained
wR(F^2) = 0.187	w = 1/[σ^2(Fo^2) + (0.0571P)^2 + 2.4946P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
3117 reflections	Δρmax = 0.18 e Å^−3
242 parameters	Δρmin = −0.36 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0039 (7)

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	0.35956 (9)	0.2042 (2)	0.9194 (2)	0.0699 (8)
H1	0.3372	0.2085	0.8673	0.105*
O2	0.47282 (8)	1.0823 (2)	0.8757 (2)	0.0676 (8)
O3	0.33289 (8)	1.1129 (2)	0.6432 (2)	0.0605 (7)
O4	0.5000	0.6796 (5)	0.2500	0.1224 (17)
H20	0.4899	0.7286	0.2989	0.184*
N1	0.44358 (9)	0.7579 (3)	0.8779 (3)	0.0567 (8)
N2	0.46700 (9)	0.8721 (3)	0.9037 (3)	0.0572 (8)
H2	0.4907	0.8734	0.9577	0.069*
N3	0.27664 (9)	1.2141 (3)	0.7713 (3)	0.0552 (8)
C1	0.38355 (12)	0.3144 (3)	0.9218 (3)	0.0546 (9)
C2	0.38057 (12)	0.3950 (3)	0.8245 (3)	0.0553 (9)
H2A	0.3622	0.3729	0.7538	0.066*
C3	0.40460 (11)	0.5066 (3)	0.8322 (3)	0.0551 (9)
H3	0.4027	0.5590	0.7660	0.066*
C4	0.43196 (11)	0.5436 (3)	0.9373 (3)	0.0514 (9)
C5	0.43624 (12)	0.4594 (3)	1.0321 (3)	0.0581 (10)
H5	0.4556	0.4797	1.1018	0.070*
C6	0.41236 (12)	0.3465 (3)	1.0248 (3)	0.0625 (10)
H6	0.4156	0.2915	1.0895	0.075*
C7	0.45454 (11)	0.6676 (3)	0.9520 (3)	0.0547 (9)
H7	0.4773	0.6811	1.0166	0.066*
C8	0.45321 (11)	0.9804 (3)	0.8454 (3)	0.0511 (9)
C9	0.41337 (12)	0.9737 (3)	0.7488 (3)	0.0630 (10)
H9A	0.3860	0.9767	0.7837	0.076*
H9B	0.4139	0.8920	0.7091	0.076*
C10	0.41111 (11)	1.0783 (4)	0.6579 (3)	0.0600 (10)
H10A	0.4149	1.1605	0.6975	0.072*
H10B	0.4357	1.0677	0.6132	0.072*
C11	0.36679 (11)	1.0763 (4)	0.5748 (3)	0.0614 (10)
H11A	0.3674	1.1358	0.5102	0.074*
H11B	0.3606	0.9913	0.5421	0.074*
C12	0.28823 (11)	1.1024 (3)	0.5954 (3)	0.0496 (9)
C13	0.27126 (12)	1.0486 (3)	0.4891 (3)	0.0565 (9)
H13	0.2908	1.0149	0.4418	0.068*
C14	0.22403 (13)	1.0442 (3)	0.4511 (3)	0.0622 (10)
H14	0.2127	1.0056	0.3791	0.075*
C15	0.19476 (13)	1.0945 (3)	0.5163 (4)	0.0626 (10)
H15	0.1637	1.0898	0.4893	0.075*
C16	0.21118 (11)	1.1545 (3)	0.6257 (3)	0.0533 (9)
C17	0.18326 (13)	1.2158 (4)	0.6962 (4)	0.0637 (10)
H17	0.1520	1.2164	0.6727	0.076*
C18	0.20197 (14)	1.2736 (4)	0.7978 (4)	0.0692 (11)
H18	0.1838	1.3153	0.8442	0.083*
C19	0.24899 (13)	1.2701 (4)	0.8326 (4)	0.0649 (10)
H19	0.2613	1.3097	0.9032	0.078*
C20	0.25844 (11)	1.1569 (3)	0.6668 (3)	0.0478 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0747 (18)	0.0550 (16)	0.0739 (19)	−0.0169 (13)	−0.0058 (14)	0.0111 (13)
O2	0.0666 (17)	0.0543 (16)	0.0755 (18)	−0.0156 (13)	−0.0074 (14)	0.0019 (13)
O3	0.0481 (14)	0.0703 (17)	0.0613 (15)	0.0026 (12)	0.0039 (12)	−0.0158 (13)
O4	0.141 (4)	0.109 (4)	0.114 (4)	0.000	0.013 (3)	0.000
N1	0.0551 (18)	0.0462 (18)	0.066 (2)	−0.0064 (14)	0.0020 (15)	0.0010 (16)
N2	0.0522 (17)	0.0499 (18)	0.0643 (19)	−0.0096 (14)	−0.0059 (14)	0.0009 (15)
N3	0.0524 (17)	0.0484 (18)	0.064 (2)	−0.0031 (14)	0.0063 (15)	−0.0029 (15)
C1	0.055 (2)	0.043 (2)	0.064 (2)	−0.0017 (17)	0.0044 (19)	−0.0033 (18)
C2	0.063 (2)	0.048 (2)	0.051 (2)	−0.0030 (18)	−0.0009 (17)	−0.0008 (17)
C3	0.064 (2)	0.051 (2)	0.049 (2)	0.0007 (18)	0.0069 (18)	0.0058 (17)
C4	0.048 (2)	0.046 (2)	0.059 (2)	0.0013 (16)	0.0064 (17)	0.0016 (17)
C5	0.058 (2)	0.056 (2)	0.055 (2)	−0.0040 (18)	−0.0047 (18)	0.0017 (19)
C6	0.072 (2)	0.053 (2)	0.059 (2)	−0.006 (2)	0.001 (2)	0.0119 (19)
C7	0.048 (2)	0.051 (2)	0.063 (2)	−0.0026 (17)	0.0030 (17)	0.0003 (19)
C8	0.047 (2)	0.045 (2)	0.059 (2)	−0.0037 (17)	0.0026 (17)	−0.0004 (18)
C9	0.063 (2)	0.051 (2)	0.069 (2)	−0.0076 (18)	−0.008 (2)	0.0007 (19)
C10	0.050 (2)	0.068 (2)	0.063 (2)	−0.0010 (18)	0.0090 (18)	0.005 (2)
C11	0.061 (2)	0.062 (2)	0.061 (2)	0.0082 (19)	0.010 (2)	0.0068 (19)
C12	0.045 (2)	0.042 (2)	0.059 (2)	−0.0029 (15)	0.0014 (17)	−0.0001 (17)
C13	0.063 (2)	0.048 (2)	0.057 (2)	−0.0026 (17)	0.0042 (19)	−0.0045 (17)
C14	0.071 (3)	0.051 (2)	0.059 (2)	−0.0104 (19)	−0.008 (2)	−0.0001 (19)
C15	0.053 (2)	0.052 (2)	0.077 (3)	−0.0098 (18)	−0.007 (2)	0.007 (2)
C16	0.051 (2)	0.040 (2)	0.066 (2)	−0.0036 (16)	0.0009 (18)	0.0076 (18)
C17	0.050 (2)	0.057 (2)	0.083 (3)	0.0037 (18)	0.009 (2)	0.006 (2)
C18	0.065 (3)	0.064 (3)	0.080 (3)	0.009 (2)	0.018 (2)	−0.003 (2)
C19	0.068 (3)	0.060 (2)	0.066 (2)	0.004 (2)	0.012 (2)	−0.009 (2)
C20	0.052 (2)	0.0364 (19)	0.053 (2)	−0.0028 (15)	0.0026 (17)	0.0000 (16)

Geometric parameters (Å, º)

O1—C1	1.355 (4)	C8—C9	1.488 (5)
O1—H1	0.8200	C9—C10	1.505 (5)
O2—C8	1.238 (4)	C9—H9A	0.9700
O3—C12	1.362 (4)	C9—H9B	0.9700
O3—C11	1.432 (4)	C10—C11	1.499 (5)
O4—H20	0.8500	C10—H10A	0.9700
N1—C7	1.277 (4)	C10—H10B	0.9700
N1—N2	1.391 (4)	C11—H11A	0.9700
N2—C8	1.345 (4)	C11—H11B	0.9700
N2—H2	0.8600	C12—C13	1.362 (4)
N3—C19	1.308 (4)	C12—C20	1.424 (5)
N3—C20	1.368 (4)	C13—C14	1.408 (5)
C1—C6	1.383 (5)	C13—H13	0.9300
C1—C2	1.389 (5)	C14—C15	1.348 (5)
C2—C3	1.367 (5)	C14—H14	0.9300
C2—H2A	0.9300	C15—C16	1.416 (5)
C3—C4	1.394 (5)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.408 (5)
C4—C5	1.389 (5)	C16—C20	1.414 (5)
C4—C7	1.459 (5)	C17—C18	1.349 (5)
C5—C6	1.376 (5)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.397 (5)
C6—H6	0.9300	C18—H18	0.9300
C7—H7	0.9300	C19—H19	0.9300
C1—O1—H1	109.5	C9—C10—H10A	109.4
C12—O3—C11	119.6 (3)	C11—C10—H10B	109.4
C7—N1—N2	115.4 (3)	C9—C10—H10B	109.4
C8—N2—N1	121.0 (3)	H10A—C10—H10B	108.0
C8—N2—H2	119.5	O3—C11—C10	106.3 (3)
N1—N2—H2	119.5	O3—C11—H11A	110.5
C19—N3—C20	118.0 (3)	C10—C11—H11A	110.5
O1—C1—C6	118.5 (3)	O3—C11—H11B	110.5
O1—C1—C2	122.4 (3)	C10—C11—H11B	110.5
C6—C1—C2	119.1 (3)	H11A—C11—H11B	108.7
C3—C2—C1	120.2 (3)	O3—C12—C13	126.1 (3)
C3—C2—H2A	119.9	O3—C12—C20	113.7 (3)
C1—C2—H2A	119.9	C13—C12—C20	120.2 (3)
C2—C3—C4	121.4 (3)	C12—C13—C14	119.8 (3)
C2—C3—H3	119.3	C12—C13—H13	120.1
C4—C3—H3	119.3	C14—C13—H13	120.1
C5—C4—C3	117.7 (3)	C15—C14—C13	121.7 (4)
C5—C4—C7	119.5 (3)	C15—C14—H14	119.2
C3—C4—C7	122.8 (3)	C13—C14—H14	119.2
C6—C5—C4	121.2 (3)	C14—C15—C16	120.1 (3)
C6—C5—H5	119.4	C14—C15—H15	119.9
C4—C5—H5	119.4	C16—C15—H15	119.9
C5—C6—C1	120.3 (3)	C17—C16—C20	117.1 (3)
C5—C6—H6	119.9	C17—C16—C15	123.9 (3)
C1—C6—H6	119.9	C20—C16—C15	119.0 (3)
N1—C7—C4	121.2 (3)	C18—C17—C16	119.9 (3)
N1—C7—H7	119.4	C18—C17—H17	120.1
C4—C7—H7	119.4	C16—C17—H17	120.1
O2—C8—N2	119.6 (3)	C17—C18—C19	119.3 (4)
O2—C8—C9	122.2 (3)	C17—C18—H18	120.4
N2—C8—C9	118.1 (3)	C19—C18—H18	120.4
C8—C9—C10	114.8 (3)	N3—C19—C18	123.7 (4)
C8—C9—H9A	108.6	N3—C19—H19	118.2
C10—C9—H9A	108.6	C18—C19—H19	118.2
C8—C9—H9B	108.6	N3—C20—C16	122.0 (3)
C10—C9—H9B	108.6	N3—C20—C12	118.8 (3)
H9A—C9—H9B	107.5	C16—C20—C12	119.1 (3)
C11—C10—C9	111.3 (3)	H20—O4—H20A	105.8
C11—C10—H10A	109.4
C7—N1—N2—C8	−167.8 (3)	C11—O3—C12—C20	−172.5 (3)
O1—C1—C2—C3	178.4 (3)	O3—C12—C13—C14	179.8 (3)
C6—C1—C2—C3	−2.3 (5)	C20—C12—C13—C14	−1.5 (5)
C1—C2—C3—C4	−1.0 (5)	C12—C13—C14—C15	1.4 (5)
C2—C3—C4—C5	3.9 (5)	C13—C14—C15—C16	0.4 (5)
C2—C3—C4—C7	−173.8 (3)	C14—C15—C16—C17	176.3 (3)
C3—C4—C5—C6	−3.5 (5)	C14—C15—C16—C20	−2.0 (5)
C7—C4—C5—C6	174.3 (3)	C20—C16—C17—C18	0.2 (5)
C4—C5—C6—C1	0.3 (6)	C15—C16—C17—C18	−178.2 (3)
O1—C1—C6—C5	−178.0 (3)	C16—C17—C18—C19	−1.0 (6)
C2—C1—C6—C5	2.7 (5)	C20—N3—C19—C18	0.6 (5)
N2—N1—C7—C4	178.6 (3)	C17—C18—C19—N3	0.6 (6)
C5—C4—C7—N1	−164.0 (3)	C19—N3—C20—C16	−1.4 (5)
C3—C4—C7—N1	13.7 (5)	C19—N3—C20—C12	176.2 (3)
N1—N2—C8—O2	175.1 (3)	C17—C16—C20—N3	1.0 (5)
N1—N2—C8—C9	−2.7 (5)	C15—C16—C20—N3	179.4 (3)
O2—C8—C9—C10	25.9 (5)	C17—C16—C20—C12	−176.5 (3)
N2—C8—C9—C10	−156.4 (3)	C15—C16—C20—C12	1.9 (5)
C8—C9—C10—C11	−171.3 (3)	O3—C12—C20—N3	1.1 (4)
C12—O3—C11—C10	−170.8 (3)	C13—C12—C20—N3	−177.8 (3)
C9—C10—C11—O3	68.2 (4)	O3—C12—C20—C16	178.7 (3)
C11—O3—C12—C13	6.3 (5)	C13—C12—C20—C16	−0.1 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3^i	0.82	1.96	2.766 (4)	168
O4—H20···O2^ii	0.85	2.26	3.054 (5)	156
N2—H2···O2^iii	0.86	2.09	2.891 (4)	155

Symmetry codes: (i) x, y−1, z; (ii) x, −y+2, z−1/2; (iii) −x+1, −y+2, −z+2.