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In the crystal structure of the title compound, C15H15N3O·H2O, O—H...O, O—H...N, N—H...O and C—H...O hydrogen bonds occur.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029212/at2330sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029212/at2330Isup2.hkl
Contains datablock I

CCDC reference: 654991

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.045
  • wR factor = 0.132
  • Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level A RADNT01_ALERT_1_A The radiation type should contain one of the following * 'Cu K\a' * 'Mo K\a' * 'Ag K\a' * neutron * synchrotron
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 0 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

Comment top

As part of our ongoing studies of the coordination chemistry of aroylhydrazones ligands (Tai et al., 2003), we now report the synthesis and structure of the title compound, (I), (Fig. 1).

In the molecule of (I), both C7—N3 [1.269 (3) Å] and C6—O1 [1.216 (2) Å] are close to double-bond separations, indicating that the Lewis structure shown in the scheme is only an approximation to the electron distribution in the molecule. Otherwise, the geometrical parameters for (I) are normal. The dihedral angle between the pyridine and benzene ring mean planes is 10.69 (10)°, indicating that the molecule is non-planar, which perhaps correlates with the intramolecular O—H···O hydrogen bond (Table 1). An intermolecular N—H···O link also occurs.

Related literature top

For related literature, see: Tai et al. (2003).

Experimental top

10 mmol of 3,4-Dimethylbenzaldehyde was added to a solution of nicotinic acid hydrazine (10 mmol) in 10 ml of ethanol. The mixture was continuously stirred for 3 h at refluxing temperature, evaporating some ethanol, then, upon cooling, the solid product was collected by filtration and dried in vacuo (yield 68%). Clear blocks of (I) were obtained by evaporation from a methanol solution after five days.

Refinement top

The H atoms were placed geometrically (C—H = 0.93 - 0.96 Å, O—H = 0.85 Å, N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(Cmethyl or Owater).

Structure description top

As part of our ongoing studies of the coordination chemistry of aroylhydrazones ligands (Tai et al., 2003), we now report the synthesis and structure of the title compound, (I), (Fig. 1).

In the molecule of (I), both C7—N3 [1.269 (3) Å] and C6—O1 [1.216 (2) Å] are close to double-bond separations, indicating that the Lewis structure shown in the scheme is only an approximation to the electron distribution in the molecule. Otherwise, the geometrical parameters for (I) are normal. The dihedral angle between the pyridine and benzene ring mean planes is 10.69 (10)°, indicating that the molecule is non-planar, which perhaps correlates with the intramolecular O—H···O hydrogen bond (Table 1). An intermolecular N—H···O link also occurs.

For related literature, see: Tai et al. (2003).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 30% displacement ellipsoids
3,4-Dimethylbenzaldehyde (3-pyridylcarbonyl)hydrazone monohydrate top
Crystal data top
C15H15N3O·H2OF(000) = 576
Mr = 271.32Dx = 1.270 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2 y b cCell parameters from 1686 reflections
a = 13.4762 (19) Åθ = 2.7–26.9°
b = 6.5174 (14) ŵ = 0.09 mm1
c = 16.497 (2) ÅT = 298 K
β = 101.629 (2)°Block, colourless
V = 1419.2 (4) Å30.56 × 0.53 × 0.49 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2475 independent reflections
Radiation source: fine-focus sealed tube1583 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
φ and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1515
Tmin = 0.953, Tmax = 0.959k = 77
6293 measured reflectionsl = 1319
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0593P)2 + 0.2072P]
where P = (Fo2 + 2Fc2)/3
2475 reflections(Δ/σ)max < 0.001
183 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C15H15N3O·H2OV = 1419.2 (4) Å3
Mr = 271.32Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.4762 (19) ŵ = 0.09 mm1
b = 6.5174 (14) ÅT = 298 K
c = 16.497 (2) Å0.56 × 0.53 × 0.49 mm
β = 101.629 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2475 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
1583 reflections with I > 2σ(I)
Tmin = 0.953, Tmax = 0.959Rint = 0.038
6293 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.132H-atom parameters constrained
S = 1.03Δρmax = 0.21 e Å3
2475 reflectionsΔρmin = 0.18 e Å3
183 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
xyzUiso*/Ueq
O10.32848 (12)0.7209 (2)0.01437 (8)0.0570 (6)
N10.40161 (16)1.0572 (3)0.20590 (10)0.0613 (7)
N20.30314 (13)1.0062 (3)0.05661 (9)0.0478 (6)
N30.26026 (13)0.8926 (3)0.11142 (10)0.0472 (6)
C10.37042 (16)0.9576 (3)0.14497 (12)0.0508 (8)
C20.37106 (14)1.0398 (3)0.06760 (11)0.0374 (6)
C30.40561 (17)1.2374 (3)0.05342 (12)0.0499 (8)
C40.44022 (17)1.3419 (4)0.11451 (13)0.0565 (8)
C50.43719 (17)1.2463 (4)0.18867 (13)0.0571 (9)
C60.33334 (15)0.9064 (3)0.00641 (11)0.0411 (7)
C70.23315 (15)0.9945 (3)0.16883 (12)0.0468 (7)
C80.18329 (15)0.8997 (3)0.22987 (11)0.0424 (7)
C90.17182 (15)1.0139 (3)0.29861 (12)0.0467 (7)
C100.12531 (15)0.9365 (4)0.35975 (12)0.0469 (8)
C110.08658 (15)0.7372 (4)0.35100 (12)0.0477 (8)
C120.09697 (16)0.6241 (4)0.28210 (12)0.0505 (8)
C130.14457 (16)0.7015 (3)0.22211 (12)0.0491 (8)
C140.11591 (19)1.0666 (4)0.43276 (14)0.0676 (10)
C150.03416 (19)0.6467 (4)0.41503 (14)0.0705 (10)
O20.32861 (13)0.4266 (2)0.11411 (8)0.0642 (6)
H10.346700.824200.155200.0610*
H20.310501.136800.062300.0570*
H30.405601.300100.002800.0600*
H40.465201.474800.105600.0680*
H50.461401.317500.229500.0690*
H70.245601.134900.172000.0560*
H90.196401.147600.303700.0560*
H120.071000.491600.276100.0610*
H130.150700.621500.176700.0590*
H14A0.150101.194800.429900.1010*
H14B0.146000.996500.482900.1010*
H14C0.045601.091700.432300.1010*
H15A0.015300.507400.400500.1060*
H15B0.025400.725300.417400.1060*
H15C0.079200.649500.468100.1060*
H2A0.334400.530200.084100.0770*
H2B0.353200.456400.164300.0770*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0900 (12)0.0355 (10)0.0492 (9)0.0060 (8)0.0226 (8)0.0005 (7)
N10.0875 (14)0.0591 (14)0.0439 (10)0.0084 (11)0.0289 (10)0.0033 (10)
N20.0710 (12)0.0351 (11)0.0436 (9)0.0046 (9)0.0266 (9)0.0025 (8)
N30.0601 (11)0.0424 (11)0.0436 (10)0.0037 (9)0.0215 (8)0.0064 (8)
C10.0706 (15)0.0408 (14)0.0438 (12)0.0054 (11)0.0179 (11)0.0053 (10)
C20.0438 (11)0.0353 (12)0.0338 (10)0.0004 (9)0.0092 (8)0.0001 (9)
C30.0635 (14)0.0491 (15)0.0400 (11)0.0101 (11)0.0171 (10)0.0062 (10)
C40.0690 (15)0.0501 (15)0.0541 (13)0.0172 (12)0.0212 (11)0.0038 (11)
C50.0675 (15)0.0621 (18)0.0476 (13)0.0086 (13)0.0254 (11)0.0073 (12)
C60.0480 (12)0.0398 (14)0.0358 (11)0.0027 (10)0.0090 (9)0.0014 (9)
C70.0574 (13)0.0394 (13)0.0472 (12)0.0044 (11)0.0189 (10)0.0020 (10)
C80.0445 (12)0.0422 (14)0.0429 (11)0.0020 (10)0.0145 (9)0.0031 (9)
C90.0497 (13)0.0406 (13)0.0525 (12)0.0036 (10)0.0168 (10)0.0026 (10)
C100.0455 (12)0.0555 (15)0.0413 (12)0.0025 (11)0.0126 (9)0.0002 (10)
C110.0442 (12)0.0571 (16)0.0441 (12)0.0003 (11)0.0143 (9)0.0074 (11)
C120.0510 (13)0.0455 (14)0.0566 (14)0.0101 (11)0.0150 (11)0.0029 (11)
C130.0551 (13)0.0490 (15)0.0463 (12)0.0040 (11)0.0175 (10)0.0030 (10)
C140.0730 (16)0.0771 (19)0.0589 (14)0.0036 (14)0.0279 (12)0.0122 (13)
C150.0730 (17)0.082 (2)0.0650 (15)0.0105 (14)0.0343 (13)0.0083 (14)
O20.1121 (13)0.0394 (10)0.0449 (8)0.0104 (9)0.0250 (9)0.0012 (7)
Geometric parameters (Å, º) top
O1—C61.216 (2)C10—C141.499 (3)
O2—H2A0.8500C11—C121.385 (3)
O2—H2B0.8500C11—C151.505 (3)
N1—C11.334 (3)C12—C131.379 (3)
N1—C51.332 (3)C1—H10.9300
N2—N31.382 (2)C3—H30.9300
N2—C61.357 (3)C4—H40.9300
N3—C71.269 (3)C5—H50.9300
N2—H20.8600C7—H70.9300
C1—C21.383 (3)C9—H90.9300
C2—C31.373 (3)C12—H120.9300
C2—C61.497 (3)C13—H130.9300
C3—C41.374 (3)C14—H14B0.9600
C4—C51.366 (3)C14—H14C0.9600
C7—C81.456 (3)C14—H14A0.9600
C8—C91.391 (3)C15—H15C0.9600
C8—C131.389 (3)C15—H15A0.9600
C9—C101.386 (3)C15—H15B0.9600
C10—C111.396 (4)
O1···O22.858 (2)C14···H15B2.9100
O1···N32.678 (2)C15···H14B2.8400
O1···C3i3.420 (3)C15···H14C2.9200
O1···C14ii3.387 (3)H1···O12.4800
O1···C10ii3.251 (3)H1···C13ii3.0500
O2···N33.171 (2)H1···C8ii2.9800
O2···C7i3.297 (3)H2···O2v2.0700
O2···N2i2.897 (2)H2···C32.5900
O2···C3i3.375 (3)H2···H72.1600
O2···O12.858 (2)H2···H32.1200
O2···N1iii2.936 (2)H2A···N32.6400
O1···H2A2.0300H2A···O12.0300
O1···H12.4800H2A···C4iv3.0900
O1···H14Bii2.8300H2A···C62.8700
O2···H3i2.5100H2A···H3i2.4000
O2···H7i2.4900H2B···H7i2.5700
O2···H4iv2.8800H2B···C5iii2.7900
O2···H2i2.0700H2B···N1iii2.1100
N1···O2ii2.936 (2)H3···N22.6600
N2···O2v2.897 (2)H3···O2v2.5100
N3···O12.678 (2)H3···H2Av2.4000
N3···O23.171 (2)H3···H22.1200
N1···H5vi2.7900H4···O2iv2.8800
N1···H2Bii2.1100H5···N1vii2.7900
N2···H32.6600H7···H2Bv2.5700
N3···H2A2.6400H7···O2v2.4900
N3···H132.6700H7···H22.1600
C1···C13ii3.529 (3)H7···H92.4000
C3···O1v3.420 (3)H9···H72.4000
C3···O2v3.375 (3)H9···H14A2.3100
C3···C6iv3.582 (3)H12···H15A2.3300
C6···C3iv3.582 (3)H13···N32.6700
C7···O2v3.297 (3)H14A···H92.3100
C10···O1iii3.251 (3)H14B···C152.8400
C13···C1iii3.529 (3)H14B···H15C2.4300
C14···O1iii3.387 (3)H14B···O1iii2.8300
C3···H22.5900H14C···C152.9200
C4···H2Aiv3.0900H14C···H15B2.5700
C5···H2Bii2.7900H15A···H122.3300
C6···H2A2.8700H15B···C142.9100
C8···H1iii2.9800H15B···H14C2.5700
C13···H1iii3.0500H15C···C142.8400
C14···H15C2.8400H15C···H14B2.4300
H2A—O2—H2B109.00C2—C1—H1118.00
C1—N1—C5116.36 (18)N1—C1—H1118.00
N3—N2—C6118.30 (18)C2—C3—H3120.00
N2—N3—C7115.41 (18)C4—C3—H3120.00
N3—N2—H2121.00C3—C4—H4121.00
C6—N2—H2121.00C5—C4—H4121.00
N1—C1—C2124.26 (19)C4—C5—H5118.00
C3—C2—C6125.41 (17)N1—C5—H5118.00
C1—C2—C3117.35 (18)N3—C7—H7119.00
C1—C2—C6117.24 (17)C8—C7—H7119.00
C2—C3—C4119.58 (19)C10—C9—H9119.00
C3—C4—C5118.5 (2)C8—C9—H9119.00
N1—C5—C4123.9 (2)C11—C12—H12119.00
N2—C6—C2115.69 (17)C13—C12—H12119.00
O1—C6—N2122.78 (18)C12—C13—H13120.00
O1—C6—C2121.52 (17)C8—C13—H13120.00
N3—C7—C8122.44 (18)C10—C14—H14A109.00
C7—C8—C9118.65 (18)C10—C14—H14B109.00
C7—C8—C13123.22 (17)H14A—C14—H14B109.00
C9—C8—C13118.12 (18)H14A—C14—H14C110.00
C8—C9—C10122.66 (19)C10—C14—H14C109.00
C11—C10—C14121.25 (19)H14B—C14—H14C109.00
C9—C10—C11118.55 (19)C11—C15—H15B110.00
C9—C10—C14120.2 (2)C11—C15—H15C109.00
C10—C11—C12118.8 (2)C11—C15—H15A109.00
C10—C11—C15120.71 (19)H15A—C15—H15C109.00
C12—C11—C15120.5 (2)H15B—C15—H15C109.00
C11—C12—C13122.2 (2)H15A—C15—H15B109.00
C8—C13—C12119.63 (19)
C5—N1—C1—C21.4 (3)N3—C7—C8—C9169.1 (2)
C1—N1—C5—C42.0 (4)N3—C7—C8—C1312.3 (3)
C6—N2—N3—C7179.72 (18)C7—C8—C9—C10179.93 (19)
N3—N2—C6—O13.4 (3)C13—C8—C9—C101.2 (3)
N3—N2—C6—C2175.06 (16)C7—C8—C13—C12179.0 (2)
N2—N3—C7—C8177.64 (17)C9—C8—C13—C120.3 (3)
N1—C1—C2—C30.4 (3)C8—C9—C10—C111.4 (3)
N1—C1—C2—C6180.0 (2)C8—C9—C10—C14179.5 (2)
C1—C2—C3—C41.8 (3)C9—C10—C11—C120.6 (3)
C6—C2—C3—C4178.6 (2)C9—C10—C11—C15179.2 (2)
C1—C2—C6—O119.6 (3)C14—C10—C11—C12179.7 (2)
C1—C2—C6—N2158.97 (18)C14—C10—C11—C150.1 (3)
C3—C2—C6—O1160.9 (2)C10—C11—C12—C130.2 (3)
C3—C2—C6—N220.6 (3)C15—C11—C12—C13180.0 (2)
C2—C3—C4—C51.3 (3)C11—C12—C13—C80.4 (3)
C3—C4—C5—N10.7 (4)
Symmetry codes: (i) x, y1, z; (ii) x, y+3/2, z1/2; (iii) x, y+3/2, z+1/2; (iv) x+1, y+2, z; (v) x, y+1, z; (vi) x+1, y1/2, z1/2; (vii) x+1, y+1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2v0.862.072.897 (2)162
O2—H2A···O10.852.032.858 (2)163
O2—H2B···N1iii0.852.112.936 (2)163
C1—H1···O10.932.482.799 (2)100
C3—H3···O2v0.932.513.375 (3)156
C7—H7···O2v0.932.493.297 (3)145
Symmetry codes: (iii) x, y+3/2, z+1/2; (v) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC15H15N3O·H2O
Mr271.32
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)13.4762 (19), 6.5174 (14), 16.497 (2)
β (°) 101.629 (2)
V3)1419.2 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.56 × 0.53 × 0.49
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.953, 0.959
No. of measured, independent and
observed [I > 2σ(I)] reflections
6293, 2475, 1583
Rint0.038
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.132, 1.03
No. of reflections2475
No. of parameters183
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.18

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.862.072.897 (2)162
O2—H2A···O10.852.032.858 (2)163
O2—H2B···N1ii0.852.112.936 (2)163
C1—H1···O10.932.482.799 (2)100
C3—H3···O2i0.932.513.375 (3)156
C7—H7···O2i0.932.493.297 (3)145
Symmetry codes: (i) x, y+1, z; (ii) x, y+3/2, z+1/2.
 

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