organic compounds
N′-[(1E)-4-Hydroxy-3-methoxybenzylidene]isonicotinohydrazide monohydrate
aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, bDepartment of Pharmaceutical Chemistry, JSS College of Pharmacy, JSS University, Mysuru 570 015, Karnataka, India, and cDepartment of Pharmaceutical Chemistry, Sri Adichunchanagiri College of Pharmacy, B G Nagara, Mandya District 571 448, Karnataka, India
*Correspondence e-mail: devarajegowda@yahoo.com
In the title hydrate, C14H13N3O3·H2O, the dihedral angle between the pyridine and benzene rings is 2.52 (9)°. Intramolecular O—H⋯O hydrogen bonds occur. In the crystal, O—H⋯O, O—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds link the components into a three-dimensional network. π–π interactions are also observed.
Keywords: crystal structure; hydrazone derivative; pyridine; dihedral angle; hydrogen bonding.
CCDC reference: 1498730
Structure description
et al., 2011; Koçyiğit Kaymakçıoğlu & Rollas, 2002), anticancer (Bhat et al., 2015), antifungal, antimicrobial, antiviral and antimalarial agents (Maccari et al., 2005; Mallikarjuna et al., 2009; Bekhit et al., 2015). The development of new classes of may overcome antimicrobial resistance.
have been reported to be antitubercular (VavříkováThe . The dihedral angle between the pyridine ring and the benzene rings is 2.52 (9)°. Intramolecular O—H⋯O hydrogen bonds (Table 1) occur. In the crystal, O—H⋯O, O—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds (Table 1) link the components into a three-dimensional network. In addition, π–π interactions are observed between the pyridine and benzene rings of neighbouring molecules with centroid–centroid distances of 3.8251 (11) and 3.8984 (11) Å. The crystal packing is illustrated in Fig. 2.
of the title compound is shown in Fig. 1Synthesis and crystallization
Equimolar quantities of vanillin (50 mmol) and isonicotinic acid hydrazide (50 mmol) were heated to reflux in the presence of absolute ethanol (50 ml) for 6 h; the completion of the reaction was monitored by TLC. After cooling and concentration of reaction mixture, the product was added to ice-cold water. The precipitated product was collected and dried. The crude product was recrystallized from 70 v/v ethanol solution, affording colourless prismatic crystals (yield 82%).
Spectroscopic data: IR (KBr disk, cm-1) 3356 (OH), 3324 (NH), 2969 (C—H), 1590 (Ar—C=C), 1265 (–OCH3); 1H NMR (400 MHz, DMSO-d6): 11.85 (s, 1H), 9.58 (s, 1H), 8.75 (s, 2H), 8.32 (s, 1H), 7.79 (d, 2H), 7.30 (d, 1H), 7.10 (dd, 1H), 6.83 (d, 1H). 3.81 (s, 3H); LC–MS m/z: 272.15 (M + H)+.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
|
Structural data
CCDC reference: 1498730
10.1107/S2414314616013006/bv4002sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616013006/bv4002Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616013006/bv4002Isup3.cml
Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2015b).C14H13N3O3·H2O | Dx = 1.401 Mg m−3 |
Mr = 289.29 | Melting point: 298 K |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54178 Å |
a = 8.3687 (7) Å | Cell parameters from 2249 reflections |
b = 13.0913 (10) Å | θ = 4.9–64.5° |
c = 12.6778 (11) Å | µ = 0.88 mm−1 |
β = 99.086 (5)° | T = 296 K |
V = 1371.5 (2) Å3 | Prism, colourless |
Z = 4 | 0.24 × 0.20 × 0.12 mm |
F(000) = 576 |
Bruker SMART CCD area-detector diffractometer | 2249 independent reflections |
Radiation source: fine-focus sealed tube | 1805 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
ω and φ scans | θmax = 64.5°, θmin = 4.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) | h = −7→9 |
Tmin = 0.770, Tmax = 1.000 | k = −14→15 |
7361 measured reflections | l = −14→12 |
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.059P)2 + 0.2398P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.114 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 0.25 e Å−3 |
2249 reflections | Δρmin = −0.25 e Å−3 |
251 parameters | Extinction correction: SHELXL-2014/7 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0065 (7) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.01283 (15) | 0.81847 (9) | 0.90314 (11) | 0.0528 (4) | |
O2 | −0.04008 (15) | 0.61830 (10) | 0.93903 (12) | 0.0539 (4) | |
O3 | 0.81796 (17) | 0.55219 (9) | 0.64551 (13) | 0.0627 (4) | |
O4 | 0.7956 (2) | 0.43537 (13) | 0.83061 (19) | 0.0730 (5) | |
N5 | 1.22351 (17) | 0.77082 (12) | 0.50647 (12) | 0.0476 (4) | |
N6 | 0.72171 (17) | 0.70837 (12) | 0.67777 (13) | 0.0439 (4) | |
N7 | 0.59405 (17) | 0.66654 (11) | 0.72119 (12) | 0.0469 (4) | |
C8 | 0.0359 (3) | 0.92178 (15) | 0.8789 (2) | 0.0645 (7) | |
C9 | 0.12124 (18) | 0.74987 (12) | 0.87380 (13) | 0.0378 (4) | |
C10 | 0.25461 (19) | 0.77494 (14) | 0.82747 (14) | 0.0404 (4) | |
C11 | 0.35901 (19) | 0.69995 (13) | 0.80039 (14) | 0.0413 (4) | |
C12 | 0.3261 (2) | 0.59800 (14) | 0.82145 (16) | 0.0478 (5) | |
C13 | 0.1922 (2) | 0.57302 (13) | 0.86640 (16) | 0.0468 (5) | |
C14 | 0.0886 (2) | 0.64756 (13) | 0.89347 (14) | 0.0400 (4) | |
C15 | 0.4981 (2) | 0.73119 (15) | 0.75230 (15) | 0.0452 (5) | |
C16 | 0.8276 (2) | 0.64568 (13) | 0.64171 (14) | 0.0411 (4) | |
C17 | 0.96296 (18) | 0.69426 (12) | 0.59529 (13) | 0.0361 (4) | |
C18 | 0.9779 (2) | 0.79793 (13) | 0.57671 (15) | 0.0423 (4) | |
C19 | 1.1081 (2) | 0.83129 (14) | 0.53230 (15) | 0.0446 (5) | |
C20 | 1.2073 (2) | 0.67153 (15) | 0.52461 (19) | 0.0570 (6) | |
C21 | 1.0808 (2) | 0.63071 (14) | 0.56764 (17) | 0.0499 (5) | |
H2 | −0.106 (3) | 0.678 (2) | 0.955 (2) | 0.107 (9)* | |
H6 | 0.731 (3) | 0.7757 (18) | 0.6774 (16) | 0.058 (6)* | |
H10 | 0.283 (2) | 0.8450 (16) | 0.8173 (16) | 0.058 (6)* | |
H13 | 0.168 (2) | 0.5017 (16) | 0.8816 (16) | 0.064 (6)* | |
H18 | 0.900 (2) | 0.8477 (15) | 0.5953 (15) | 0.055 (5)* | |
H12 | 0.402 (3) | 0.5455 (15) | 0.8037 (16) | 0.063 (6)* | |
H19 | 1.118 (2) | 0.9016 (16) | 0.5182 (16) | 0.058 (6)* | |
H15 | 0.519 (2) | 0.8058 (17) | 0.7452 (15) | 0.057 (6)* | |
H21 | 1.075 (3) | 0.5576 (17) | 0.5790 (17) | 0.068 (6)* | |
H20 | 1.289 (3) | 0.6279 (17) | 0.5081 (17) | 0.070 (7)* | |
H8A | −0.051 (3) | 0.9615 (18) | 0.8970 (19) | 0.080 (7)* | |
H8B | 0.143 (3) | 0.9463 (18) | 0.918 (2) | 0.089 (8)* | |
H8C | 0.031 (3) | 0.930 (2) | 0.792 (2) | 0.102 (9)* | |
H4B | 0.785 (4) | 0.475 (2) | 0.770 (2) | 0.103 (10)* | |
H4A | 0.841 (4) | 0.472 (3) | 0.867 (3) | 0.132 (15)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0479 (7) | 0.0351 (7) | 0.0847 (10) | 0.0084 (5) | 0.0386 (7) | 0.0072 (6) |
O2 | 0.0455 (8) | 0.0385 (7) | 0.0868 (11) | 0.0000 (5) | 0.0386 (7) | 0.0034 (6) |
O3 | 0.0569 (8) | 0.0407 (7) | 0.1011 (12) | −0.0071 (6) | 0.0452 (8) | −0.0036 (7) |
O4 | 0.0819 (12) | 0.0538 (9) | 0.0861 (13) | −0.0240 (8) | 0.0218 (10) | 0.0032 (9) |
N5 | 0.0380 (8) | 0.0474 (8) | 0.0618 (10) | −0.0014 (6) | 0.0216 (7) | 0.0035 (7) |
N6 | 0.0354 (8) | 0.0421 (9) | 0.0599 (10) | −0.0036 (6) | 0.0250 (7) | −0.0039 (7) |
N7 | 0.0346 (8) | 0.0539 (9) | 0.0576 (10) | −0.0046 (7) | 0.0237 (7) | −0.0048 (7) |
C8 | 0.0622 (14) | 0.0354 (10) | 0.105 (2) | 0.0109 (9) | 0.0420 (14) | 0.0106 (11) |
C9 | 0.0327 (8) | 0.0353 (9) | 0.0485 (10) | 0.0047 (7) | 0.0156 (7) | 0.0002 (7) |
C10 | 0.0348 (9) | 0.0390 (9) | 0.0504 (11) | 0.0001 (7) | 0.0160 (7) | 0.0013 (8) |
C11 | 0.0335 (9) | 0.0479 (10) | 0.0457 (10) | 0.0003 (7) | 0.0161 (7) | −0.0029 (8) |
C12 | 0.0411 (10) | 0.0431 (10) | 0.0642 (12) | 0.0057 (8) | 0.0240 (9) | −0.0066 (9) |
C13 | 0.0429 (10) | 0.0358 (9) | 0.0667 (13) | 0.0015 (7) | 0.0235 (9) | −0.0030 (9) |
C14 | 0.0351 (9) | 0.0388 (9) | 0.0498 (10) | −0.0018 (7) | 0.0183 (7) | 0.0005 (7) |
C15 | 0.0377 (10) | 0.0501 (11) | 0.0516 (11) | 0.0004 (8) | 0.0185 (8) | −0.0023 (8) |
C16 | 0.0327 (9) | 0.0404 (9) | 0.0535 (11) | −0.0031 (7) | 0.0170 (7) | −0.0030 (8) |
C17 | 0.0283 (8) | 0.0389 (8) | 0.0429 (10) | −0.0011 (6) | 0.0116 (7) | −0.0035 (7) |
C18 | 0.0356 (9) | 0.0384 (9) | 0.0557 (11) | 0.0010 (7) | 0.0155 (8) | −0.0042 (8) |
C19 | 0.0394 (10) | 0.0378 (10) | 0.0596 (12) | −0.0038 (7) | 0.0170 (8) | 0.0012 (8) |
C20 | 0.0459 (11) | 0.0466 (11) | 0.0870 (16) | 0.0072 (9) | 0.0371 (10) | 0.0075 (10) |
C21 | 0.0434 (10) | 0.0378 (10) | 0.0744 (14) | 0.0033 (8) | 0.0280 (9) | 0.0049 (9) |
O1—C9 | 1.3691 (19) | C10—C11 | 1.393 (2) |
O1—C8 | 1.407 (2) | C10—H10 | 0.96 (2) |
O2—C14 | 1.355 (2) | C11—C12 | 1.397 (3) |
O2—H2 | 0.99 (3) | C11—C15 | 1.455 (2) |
O3—C16 | 1.228 (2) | C12—C13 | 1.374 (3) |
O4—H4B | 0.92 (3) | C12—H12 | 0.99 (2) |
O4—H4A | 0.73 (3) | C13—C14 | 1.384 (2) |
N5—C19 | 1.329 (2) | C13—H13 | 0.98 (2) |
N5—C20 | 1.331 (2) | C15—H15 | 1.00 (2) |
N6—C16 | 1.340 (2) | C16—C17 | 1.498 (2) |
N6—N7 | 1.389 (2) | C17—C21 | 1.377 (2) |
N6—H6 | 0.88 (2) | C17—C18 | 1.386 (2) |
N7—C15 | 1.272 (2) | C18—C19 | 1.375 (3) |
C8—H8A | 0.95 (3) | C18—H18 | 0.97 (2) |
C8—H8B | 1.01 (3) | C19—H19 | 0.94 (2) |
C8—H8C | 1.10 (3) | C20—C21 | 1.373 (3) |
C9—C10 | 1.380 (2) | C20—H20 | 0.94 (2) |
C9—C14 | 1.397 (2) | C21—H21 | 0.97 (2) |
C9—O1—C8 | 116.83 (14) | C12—C13—H13 | 120.9 (12) |
C14—O2—H2 | 111.8 (16) | C14—C13—H13 | 117.9 (13) |
H4B—O4—H4A | 97 (3) | O2—C14—C13 | 118.52 (15) |
C19—N5—C20 | 116.19 (16) | O2—C14—C9 | 122.53 (15) |
C16—N6—N7 | 119.02 (15) | C13—C14—C9 | 118.95 (16) |
C16—N6—H6 | 123.2 (15) | N7—C15—C11 | 121.94 (18) |
N7—N6—H6 | 117.8 (15) | N7—C15—H15 | 119.6 (12) |
C15—N7—N6 | 115.06 (15) | C11—C15—H15 | 118.4 (12) |
O1—C8—H8A | 109.6 (15) | O3—C16—N6 | 123.10 (16) |
O1—C8—H8B | 109.9 (14) | O3—C16—C17 | 119.78 (15) |
H8A—C8—H8B | 111 (2) | N6—C16—C17 | 117.12 (15) |
O1—C8—H8C | 109.3 (14) | C21—C17—C18 | 117.44 (16) |
H8A—C8—H8C | 106 (2) | C21—C17—C16 | 117.37 (15) |
H8B—C8—H8C | 111 (2) | C18—C17—C16 | 125.18 (15) |
O1—C9—C10 | 125.07 (15) | C19—C18—C17 | 118.63 (16) |
O1—C9—C14 | 115.08 (14) | C19—C18—H18 | 119.2 (12) |
C10—C9—C14 | 119.85 (15) | C17—C18—H18 | 122.1 (12) |
C9—C10—C11 | 121.21 (16) | N5—C19—C18 | 124.45 (17) |
C9—C10—H10 | 120.9 (13) | N5—C19—H19 | 116.3 (13) |
C11—C10—H10 | 117.7 (13) | C18—C19—H19 | 119.3 (13) |
C10—C11—C12 | 118.41 (16) | N5—C20—C21 | 123.69 (18) |
C10—C11—C15 | 118.65 (16) | N5—C20—H20 | 117.2 (14) |
C12—C11—C15 | 122.94 (16) | C21—C20—H20 | 119.1 (14) |
C13—C12—C11 | 120.34 (16) | C20—C21—C17 | 119.60 (17) |
C13—C12—H12 | 121.8 (12) | C20—C21—H21 | 120.1 (14) |
C11—C12—H12 | 117.8 (12) | C17—C21—H21 | 120.3 (14) |
C12—C13—C14 | 121.23 (17) | ||
C16—N6—N7—C15 | −179.18 (16) | C10—C11—C15—N7 | −176.74 (17) |
C8—O1—C9—C10 | 3.4 (3) | C12—C11—C15—N7 | 3.8 (3) |
C8—O1—C9—C14 | −176.32 (19) | N7—N6—C16—O3 | −0.3 (3) |
O1—C9—C10—C11 | 179.83 (16) | N7—N6—C16—C17 | 179.83 (14) |
C14—C9—C10—C11 | −0.5 (3) | O3—C16—C17—C21 | −6.0 (3) |
C9—C10—C11—C12 | −0.2 (3) | N6—C16—C17—C21 | 173.86 (17) |
C9—C10—C11—C15 | −179.66 (16) | O3—C16—C17—C18 | 173.15 (18) |
C10—C11—C12—C13 | 0.9 (3) | N6—C16—C17—C18 | −7.0 (3) |
C15—C11—C12—C13 | −179.58 (18) | C21—C17—C18—C19 | −0.1 (3) |
C11—C12—C13—C14 | −1.1 (3) | C16—C17—C18—C19 | −179.19 (17) |
C12—C13—C14—O2 | −179.03 (18) | C20—N5—C19—C18 | 0.9 (3) |
C12—C13—C14—C9 | 0.4 (3) | C17—C18—C19—N5 | −0.8 (3) |
O1—C9—C14—O2 | −0.5 (3) | C19—N5—C20—C21 | −0.2 (3) |
C10—C9—C14—O2 | 179.79 (17) | N5—C20—C21—C17 | −0.6 (4) |
O1—C9—C14—C13 | −179.92 (16) | C18—C17—C21—C20 | 0.7 (3) |
C10—C9—C14—C13 | 0.4 (3) | C16—C17—C21—C20 | 179.90 (19) |
N6—N7—C15—C11 | −179.50 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1 | 1.00 (3) | 2.24 (3) | 2.7081 (18) | 107.4 (18) |
O2—H2···N5i | 1.00 (3) | 1.79 (3) | 2.699 (2) | 150 (2) |
O4—H4A···O2ii | 0.73 (4) | 2.28 (4) | 2.986 (2) | 163 (4) |
O4—H4B···O3 | 0.92 (3) | 1.93 (3) | 2.832 (3) | 166 (3) |
N6—H6···O4iii | 0.89 (2) | 2.10 (2) | 2.976 (2) | 169 (2) |
C8—H8A···O3iv | 0.95 (2) | 2.51 (2) | 3.390 (3) | 154 (2) |
C15—H15···O4iii | 1.00 (2) | 2.58 (2) | 3.436 (3) | 143.1 (14) |
C18—H18···O4iii | 0.977 (18) | 2.316 (18) | 3.272 (3) | 165.9 (16) |
C20—H20···O1v | 0.94 (2) | 2.56 (2) | 3.189 (2) | 124.5 (17) |
Symmetry codes: (i) x−3/2, −y+3/2, z+1/2; (ii) x+1, y, z; (iii) −x+3/2, y+1/2, −z+3/2; (iv) −x+1/2, y+1/2, −z+3/2; (v) x+3/2, −y+3/2, z−1/2. |
Acknowledgements
The authors thank the Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad, for the CCD X-ray facilities and X-ray data collection.
References
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