organic compounds
(E)-N′-(4-Pyridylmethylene)-2-(quinolin-8-yloxy)acetohydrazide sesquihydrate
aDepartment of Chemistry, Taishan University, 271021 Taian, Shandong, People's Republic of China, and bDepartment of Materials and Chemistry Engineering, Taishan University, 271021 Taian, Shandong, People's Republic of China
*Correspondence e-mail: zhengzebao@163.com
In the title compound, C17H14N4O2·1.5H2O, the mean planes of the pyridine ring and quinoline group make a dihedral angle of 21.0 (2)°. One water molecule lies on a twofold rotation axis. The organic molecules and the three water molecules are linked into infinite chains by N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds.
Experimental
Crystal data
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Refinement
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Data collection: SMART (Siemens, 1996); cell 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.
Supporting information
https://doi.org/10.1107/S1600536807066664/rk2067sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807066664/rk2067Isup2.hkl
2–(Quinolin–8–yl-oxy)acetohydrazide (0.01 mol), 4–pyridylaldehyde (0.01 mol), ethanol (40 ml) and three drops of acetic acid were added to a 100 ml flask, and refluxed for 6 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 tetrahydrofuran solution over a period of 1 d. (m.p. 361 K). Elemental analysis calc.: C 61.25, H 5.14, N 16.80%; found: C 61.19, H 5.21, N 16.77%.
All H atoms were placed in idealized calculated positions with C—H = 0.93–0.97 Å, O—H = 0.85 Å, N—H = 0.86Å and refined as riding atoms with Uiso(H) = 1.2Ueq(C or N) and Uiso(H) = 1.5Ueq(O).
8–Hydroxyquinoline and its derivatives are of the most extensively investigated ligands in the coordination chemistry (Chen & Shi, 1998; Moawad & Hanna, 2002). In course of our studies on searching for good extractants of metal ions or a biologically active material, the title compound, (I), was synthesized and its
determined. The conformation along the O1–C10–C11–N2–N3–C12–C13 bond sequence is (-)gauche–trans–trans–trans (Fig.1). The mean planes of the pyridine ring and quinoline group make a dihedral angle of the molecules are 21.0 (2)°. The two molecules and the three water molecules are linked into infinite chains by N—H···O, O—H···O and O—H···N hydrogen bonds (Fig. 2).For related literature, see: Chen & Shi (1998); Moawad & Hanna (2002).
Data collection: SMART (Siemens, 1996); cell
SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 1997b).C17H14N4O2·1.5H2O | F(000) = 1400 |
Mr = 333.35 | Dx = 1.325 Mg m−3 |
Monoclinic, C2/c | Melting point: 361 K |
Hall symbol: -c 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 16.3206 (19) Å | Cell parameters from 1750 reflections |
b = 15.6706 (19) Å | θ = 2.6–22.1° |
c = 13.5692 (16) Å | µ = 0.10 mm−1 |
β = 105.623 (3)° | T = 295 K |
V = 3342.2 (7) Å3 | Block, colorless |
Z = 8 | 0.26 × 0.22 × 0.18 mm |
Bruker SMART CCD area-detector diffractometer | 2962 independent reflections |
Radiation source: fine–focus sealed tube | 1974 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
φ and ω scans | θmax = 25.1°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −18→19 |
Tmin = 0.976, Tmax = 0.983 | k = −15→18 |
8726 measured reflections | l = −16→15 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0416P)2 + 1.6836P] where P = (Fo2 + 2Fc2)/3 |
2962 reflections | (Δ/σ)max < 0.001 |
222 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C17H14N4O2·1.5H2O | V = 3342.2 (7) Å3 |
Mr = 333.35 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 16.3206 (19) Å | µ = 0.10 mm−1 |
b = 15.6706 (19) Å | T = 295 K |
c = 13.5692 (16) Å | 0.26 × 0.22 × 0.18 mm |
β = 105.623 (3)° |
Bruker SMART CCD area-detector diffractometer | 2962 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1974 reflections with I > 2σ(I) |
Tmin = 0.976, Tmax = 0.983 | Rint = 0.034 |
8726 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.23 e Å−3 |
2962 reflections | Δρmin = −0.24 e Å−3 |
222 parameters |
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 > 2σ(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 | ||
O1 | 0.15472 (7) | 0.61002 (8) | 0.13430 (10) | 0.0522 (4) | |
O2 | −0.00480 (9) | 0.45270 (10) | 0.11135 (14) | 0.0848 (6) | |
O3 | 0.03989 (8) | 0.77138 (9) | 0.10648 (12) | 0.0679 (5) | |
H18 | 0.0924 | 0.7680 | 0.1089 | 0.102* | |
H19 | 0.0139 | 0.7832 | 0.0448 | 0.102* | |
O4 | 0.5000 | 0.38335 (19) | 0.2500 | 0.198 (2) | |
H20 | 0.4541 | 0.3547 | 0.2364 | 0.297* | |
N1 | 0.21216 (9) | 0.76870 (10) | 0.12366 (12) | 0.0480 (4) | |
N2 | −0.01021 (9) | 0.59689 (11) | 0.12749 (13) | 0.0563 (5) | |
H2 | 0.0178 | 0.6440 | 0.1386 | 0.068* | |
N3 | −0.09687 (10) | 0.59595 (12) | 0.11520 (13) | 0.0586 (5) | |
N4 | −0.39872 (12) | 0.69428 (16) | 0.07266 (16) | 0.0784 (6) | |
C1 | 0.24172 (13) | 0.84681 (13) | 0.12079 (16) | 0.0570 (6) | |
H1 | 0.2036 | 0.8919 | 0.1147 | 0.068* | |
C2 | 0.32621 (13) | 0.86644 (15) | 0.12628 (16) | 0.0621 (6) | |
H2A | 0.3437 | 0.9228 | 0.1248 | 0.074* | |
C3 | 0.38204 (13) | 0.80125 (15) | 0.13380 (16) | 0.0596 (6) | |
H3 | 0.4386 | 0.8127 | 0.1370 | 0.071* | |
C4 | 0.35495 (11) | 0.71610 (13) | 0.13688 (15) | 0.0504 (5) | |
C5 | 0.40959 (12) | 0.64574 (16) | 0.14487 (17) | 0.0642 (6) | |
H5 | 0.4662 | 0.6543 | 0.1460 | 0.077* | |
C6 | 0.38064 (13) | 0.56572 (16) | 0.15098 (18) | 0.0671 (6) | |
H6A | 0.4179 | 0.5198 | 0.1576 | 0.081* | |
C7 | 0.29443 (12) | 0.55081 (14) | 0.14739 (16) | 0.0591 (6) | |
H7 | 0.2753 | 0.4954 | 0.1514 | 0.071* | |
C8 | 0.23931 (11) | 0.61774 (13) | 0.13810 (14) | 0.0463 (5) | |
C9 | 0.26813 (11) | 0.70304 (12) | 0.13252 (13) | 0.0429 (5) | |
C10 | 0.12326 (11) | 0.52542 (12) | 0.13095 (17) | 0.0561 (6) | |
H10A | 0.1537 | 0.4956 | 0.1926 | 0.067* | |
H10B | 0.1344 | 0.4959 | 0.0730 | 0.067* | |
C11 | 0.02969 (13) | 0.52209 (15) | 0.12202 (16) | 0.0577 (6) | |
C12 | −0.12998 (13) | 0.66627 (15) | 0.13033 (16) | 0.0575 (6) | |
H12 | −0.0953 | 0.7134 | 0.1524 | 0.069* | |
C13 | −0.22215 (12) | 0.67417 (14) | 0.11357 (15) | 0.0549 (5) | |
C14 | −0.27696 (13) | 0.60665 (16) | 0.07901 (19) | 0.0730 (7) | |
H14 | −0.2559 | 0.5532 | 0.0688 | 0.088* | |
C15 | −0.36330 (15) | 0.62007 (19) | 0.0599 (2) | 0.0873 (8) | |
H15 | −0.3993 | 0.5741 | 0.0365 | 0.105* | |
C16 | −0.34569 (15) | 0.75802 (17) | 0.10755 (17) | 0.0701 (7) | |
H16 | −0.3684 | 0.8105 | 0.1185 | 0.084* | |
C17 | −0.25845 (14) | 0.75065 (15) | 0.12848 (15) | 0.0617 (6) | |
H17 | −0.2240 | 0.7976 | 0.1528 | 0.074* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0346 (7) | 0.0500 (8) | 0.0732 (10) | −0.0113 (6) | 0.0166 (6) | 0.0027 (7) |
O2 | 0.0579 (10) | 0.0641 (11) | 0.1351 (16) | −0.0255 (8) | 0.0306 (10) | 0.0071 (10) |
O3 | 0.0428 (8) | 0.0768 (10) | 0.0849 (11) | −0.0025 (7) | 0.0187 (7) | 0.0064 (8) |
O4 | 0.389 (7) | 0.066 (2) | 0.178 (4) | 0.000 | 0.143 (4) | 0.000 |
N1 | 0.0389 (9) | 0.0527 (10) | 0.0519 (10) | −0.0096 (8) | 0.0112 (7) | 0.0016 (8) |
N2 | 0.0345 (9) | 0.0646 (12) | 0.0699 (12) | −0.0164 (8) | 0.0143 (8) | 0.0004 (9) |
N3 | 0.0357 (9) | 0.0750 (13) | 0.0656 (12) | −0.0128 (9) | 0.0143 (8) | 0.0074 (10) |
N4 | 0.0464 (12) | 0.1033 (17) | 0.0859 (15) | 0.0024 (12) | 0.0187 (10) | 0.0101 (13) |
C1 | 0.0543 (13) | 0.0545 (13) | 0.0609 (14) | −0.0101 (10) | 0.0135 (10) | 0.0021 (10) |
C2 | 0.0570 (14) | 0.0624 (14) | 0.0675 (15) | −0.0236 (11) | 0.0179 (11) | −0.0018 (11) |
C3 | 0.0423 (12) | 0.0770 (16) | 0.0602 (14) | −0.0246 (12) | 0.0151 (10) | −0.0027 (12) |
C4 | 0.0366 (11) | 0.0681 (14) | 0.0476 (12) | −0.0130 (10) | 0.0130 (9) | −0.0041 (10) |
C5 | 0.0331 (11) | 0.0861 (17) | 0.0747 (16) | −0.0066 (11) | 0.0166 (10) | −0.0016 (13) |
C6 | 0.0426 (12) | 0.0750 (16) | 0.0851 (17) | 0.0079 (11) | 0.0192 (11) | 0.0010 (13) |
C7 | 0.0464 (12) | 0.0551 (13) | 0.0758 (16) | −0.0032 (10) | 0.0164 (11) | 0.0019 (11) |
C8 | 0.0311 (10) | 0.0576 (12) | 0.0498 (12) | −0.0081 (9) | 0.0103 (9) | 0.0003 (9) |
C9 | 0.0338 (10) | 0.0547 (12) | 0.0400 (11) | −0.0094 (9) | 0.0099 (8) | −0.0001 (9) |
C10 | 0.0401 (11) | 0.0504 (12) | 0.0775 (15) | −0.0104 (9) | 0.0150 (10) | 0.0061 (11) |
C11 | 0.0464 (12) | 0.0593 (14) | 0.0683 (15) | −0.0143 (11) | 0.0171 (11) | 0.0073 (11) |
C12 | 0.0435 (12) | 0.0731 (16) | 0.0559 (14) | −0.0153 (11) | 0.0137 (10) | 0.0025 (11) |
C13 | 0.0406 (11) | 0.0760 (15) | 0.0486 (12) | −0.0087 (11) | 0.0130 (9) | 0.0102 (11) |
C14 | 0.0436 (13) | 0.0765 (16) | 0.0971 (19) | −0.0079 (12) | 0.0161 (12) | 0.0066 (14) |
C15 | 0.0456 (15) | 0.092 (2) | 0.120 (2) | −0.0133 (13) | 0.0158 (14) | 0.0047 (17) |
C16 | 0.0623 (15) | 0.0892 (18) | 0.0631 (15) | 0.0073 (14) | 0.0243 (12) | 0.0065 (13) |
C17 | 0.0587 (14) | 0.0788 (16) | 0.0503 (13) | −0.0065 (12) | 0.0192 (11) | 0.0026 (11) |
O1—C8 | 1.373 (2) | C4—C9 | 1.417 (2) |
O1—C10 | 1.418 (2) | C5—C6 | 1.351 (3) |
O2—C11 | 1.215 (2) | C5—H5 | 0.9300 |
O3—H18 | 0.8499 | C6—C7 | 1.414 (3) |
O3—H19 | 0.8500 | C6—H6A | 0.9300 |
O4—H20 | 0.8501 | C7—C8 | 1.365 (3) |
N1—C1 | 1.320 (2) | C7—H7 | 0.9300 |
N1—C9 | 1.360 (2) | C8—C9 | 1.426 (3) |
N2—C11 | 1.353 (3) | C10—C11 | 1.500 (3) |
N2—N3 | 1.379 (2) | C10—H10A | 0.9700 |
N2—H2 | 0.8598 | C10—H10B | 0.9700 |
N3—C12 | 1.268 (3) | C12—C13 | 1.465 (3) |
N4—C16 | 1.323 (3) | C12—H12 | 0.9300 |
N4—C15 | 1.331 (3) | C13—C17 | 1.376 (3) |
C1—C2 | 1.395 (3) | C13—C14 | 1.383 (3) |
C1—H1 | 0.9300 | C14—C15 | 1.378 (3) |
C2—C3 | 1.354 (3) | C14—H14 | 0.9300 |
C2—H2A | 0.9300 | C15—H15 | 0.9300 |
C3—C4 | 1.410 (3) | C16—C17 | 1.380 (3) |
C3—H3 | 0.9300 | C16—H16 | 0.9300 |
C4—C5 | 1.404 (3) | C17—H17 | 0.9300 |
C8—O1—C10 | 115.81 (15) | O1—C8—C9 | 115.05 (16) |
H18—O3—H19 | 106.4 | N1—C9—C4 | 122.34 (17) |
C1—N1—C9 | 117.52 (16) | N1—C9—C8 | 119.39 (15) |
C11—N2—N3 | 118.52 (17) | C4—C9—C8 | 118.27 (17) |
C11—N2—H2 | 120.8 | O1—C10—C11 | 112.77 (17) |
N3—N2—H2 | 120.6 | O1—C10—H10A | 109.0 |
C12—N3—N2 | 116.05 (17) | C11—C10—H10A | 109.0 |
C16—N4—C15 | 116.2 (2) | O1—C10—H10B | 109.0 |
N1—C1—C2 | 124.5 (2) | C11—C10—H10B | 109.0 |
N1—C1—H1 | 117.7 | H10A—C10—H10B | 107.8 |
C2—C1—H1 | 117.7 | O2—C11—N2 | 124.59 (19) |
C3—C2—C1 | 118.2 (2) | O2—C11—C10 | 118.0 (2) |
C3—C2—H2A | 120.9 | N2—C11—C10 | 117.40 (18) |
C1—C2—H2A | 120.9 | N3—C12—C13 | 120.9 (2) |
C2—C3—C4 | 120.42 (18) | N3—C12—H12 | 119.6 |
C2—C3—H3 | 119.8 | C13—C12—H12 | 119.6 |
C4—C3—H3 | 119.8 | C17—C13—C14 | 116.83 (19) |
C5—C4—C3 | 123.23 (18) | C17—C13—C12 | 121.0 (2) |
C5—C4—C9 | 119.81 (18) | C14—C13—C12 | 122.1 (2) |
C3—C4—C9 | 116.96 (19) | C15—C14—C13 | 118.8 (2) |
C6—C5—C4 | 120.57 (19) | C15—C14—H14 | 120.6 |
C6—C5—H5 | 119.7 | C13—C14—H14 | 120.6 |
C4—C5—H5 | 119.7 | N4—C15—C14 | 124.5 (2) |
C5—C6—C7 | 120.8 (2) | N4—C15—H15 | 117.7 |
C5—C6—H6A | 119.6 | C14—C15—H15 | 117.7 |
C7—C6—H6A | 119.6 | N4—C16—C17 | 123.4 (2) |
C8—C7—C6 | 120.1 (2) | N4—C16—H16 | 118.3 |
C8—C7—H7 | 120.0 | C17—C16—H16 | 118.3 |
C6—C7—H7 | 120.0 | C13—C17—C16 | 120.3 (2) |
C7—C8—O1 | 124.51 (17) | C13—C17—H17 | 119.9 |
C7—C8—C9 | 120.43 (17) | C16—C17—H17 | 119.9 |
C11—N2—N3—C12 | 173.72 (19) | C7—C8—C9—N1 | −179.76 (18) |
C9—N1—C1—C2 | 0.0 (3) | O1—C8—C9—N1 | −0.3 (3) |
N1—C1—C2—C3 | 0.9 (3) | C7—C8—C9—C4 | 0.0 (3) |
C1—C2—C3—C4 | −0.6 (3) | O1—C8—C9—C4 | 179.47 (16) |
C2—C3—C4—C5 | −179.8 (2) | C8—O1—C10—C11 | −177.36 (17) |
C2—C3—C4—C9 | −0.4 (3) | N3—N2—C11—O2 | −3.4 (3) |
C3—C4—C5—C6 | 177.7 (2) | N3—N2—C11—C10 | 177.31 (17) |
C9—C4—C5—C6 | −1.6 (3) | O1—C10—C11—O2 | 174.94 (19) |
C4—C5—C6—C7 | 1.3 (4) | O1—C10—C11—N2 | −5.7 (3) |
C5—C6—C7—C8 | −0.3 (4) | N2—N3—C12—C13 | 176.33 (17) |
C6—C7—C8—O1 | −179.76 (19) | N3—C12—C13—C17 | −179.1 (2) |
C6—C7—C8—C9 | −0.3 (3) | N3—C12—C13—C14 | −1.2 (3) |
C10—O1—C8—C7 | −5.7 (3) | C17—C13—C14—C15 | 1.3 (3) |
C10—O1—C8—C9 | 174.83 (16) | C12—C13—C14—C15 | −176.6 (2) |
C1—N1—C9—C4 | −1.1 (3) | C16—N4—C15—C14 | −1.0 (4) |
C1—N1—C9—C8 | 178.67 (17) | C13—C14—C15—N4 | −0.2 (4) |
C5—C4—C9—N1 | −179.27 (18) | C15—N4—C16—C17 | 1.2 (4) |
C3—C4—C9—N1 | 1.3 (3) | C14—C13—C17—C16 | −1.1 (3) |
C5—C4—C9—C8 | 1.0 (3) | C12—C13—C17—C16 | 176.83 (19) |
C3—C4—C9—C8 | −178.43 (18) | N4—C16—C17—C13 | −0.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H19···N4i | 0.85 | 2.14 | 2.914 (2) | 151 |
N2—H2···O3 | 0.86 | 2.10 | 2.890 (2) | 153 |
O3—H18···N1 | 0.85 | 1.91 | 2.7582 (19) | 175 |
O4—H20···O3ii | 0.85 | 2.48 | 2.825 (2) | 105 |
Symmetry codes: (i) −x−1/2, −y+3/2, −z; (ii) −x+1/2, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C17H14N4O2·1.5H2O |
Mr | 333.35 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 295 |
a, b, c (Å) | 16.3206 (19), 15.6706 (19), 13.5692 (16) |
β (°) | 105.623 (3) |
V (Å3) | 3342.2 (7) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.26 × 0.22 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.976, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8726, 2962, 1974 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.113, 1.00 |
No. of reflections | 2962 |
No. of parameters | 222 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.24 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H19···N4i | 0.85 | 2.14 | 2.914 (2) | 150.8 |
N2—H2···O3 | 0.86 | 2.10 | 2.890 (2) | 153.4 |
O3—H18···N1 | 0.85 | 1.91 | 2.7582 (19) | 174.7 |
O4—H20···O3ii | 0.85 | 2.48 | 2.825 (2) | 105.3 |
Symmetry codes: (i) −x−1/2, −y+3/2, −z; (ii) −x+1/2, y−1/2, −z+1/2. |
Acknowledgements
This project was supported by the Postgraduate Foundation of Taishan University (No. Y05–2–02).
References
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8–Hydroxyquinoline and its derivatives are of the most extensively investigated ligands in the coordination chemistry (Chen & Shi, 1998; Moawad & Hanna, 2002). In course of our studies on searching for good extractants of metal ions or a biologically active material, the title compound, (I), was synthesized and its crystal structure determined. The conformation along the O1–C10–C11–N2–N3–C12–C13 bond sequence is (-)gauche–trans–trans–trans (Fig.1). The mean planes of the pyridine ring and quinoline group make a dihedral angle of the molecules are 21.0 (2)°. The two molecules and the three water molecules are linked into infinite chains by N—H···O, O—H···O and O—H···N hydrogen bonds (Fig. 2).