N′-[(1E)-4-Hy­droxy-3-meth­oxy­benzylidene]isonicotinohydrazide monohydrate

Roopashree, K.R.; Inturi, B.; Pujar, G.V.; Prem Kumar, S.R.; Devarajegowda, H.C.

doi:10.1107/S2414314616013006

organic compounds

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ISSN: 2414-3146

Volume 1| Part 8| August 2016| x161300

doi:10.1107/S2414314616013006

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N′-[(1E)-4-Hydroxy-3-methoxybenzylidene]isonicotinohydrazide monohydrate

K. R. Roopashree,^a Bharathkumar Inturi,^b Gurubasavaraj V. Pujar,^b S. R. Prem Kumar ^c and H. C. Devarajegowda ^a ^*

^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

Edited by R. J. Butcher, Howard University, USA (Received 1 June 2016; accepted 11 August 2016; online 26 August 2016)

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

Hydrazones have been reported to be antitubercular (Vavříková 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 hydrazones may overcome antimicrobial resistance.

The asymmetric unit of the title compound is shown in Fig. 1. 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.

Table 1
Hydrogen-bond geometry (Å, °)

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⋯O3^iv	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⋯O1^v	0.94 (2)	2.56 (2)	3.189 (2)	124.5 (17)
Symmetry codes: (i) $[x-{\script{3\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) $[x+{\script{3\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Figure 1
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.

Figure 2
The packing of molecules. Hydrogen bonds are shown as dashed lines.

Synthesis 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 refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₄H₁₃N₃O₃·H₂O
M_r	289.29
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	8.3687 (7), 13.0913 (10), 12.6778 (11)
β (°)	99.086 (5)
V (Å³)	1371.5 (2)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.88
Crystal size (mm)	0.24 × 0.20 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007 )
T_min, T_max	0.770, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7361, 2249, 1805
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.586

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.114, 1.04
No. of reflections	2249
No. of parameters	251
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.25
Computer programs: SMART and SAINT (Bruker, 2001 ), SHELXT (Sheldrick, 2015a ), SHELXL2014/7 (Sheldrick, 2015b ) and ORTEP-3 for Windows (Farrugia, 2012 ).

Structural data

CCDC reference: 1498730

Crystal structure: contains datablocks I, global. DOI: 10.1107/S2414314616013006/bv4002sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616013006/bv4002Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616013006/bv4002Isup3.cml

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: 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).

N'-[(1E)-4-Hydroxy-3-methoxybenzylidene]isonicotinohydrazide monohydrate top

Crystal data top

C₁₄H₁₃N₃O₃·H₂O	D_x = 1.401 Mg m⁻³
M_r = 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

Data collection top

Bruker SMART CCD area-detector diffractometer	2249 independent reflections
Radiation source: fine-focus sealed tube	1805 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω and φ scans	θ_max = 64.5°, θ_min = 4.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −7→9
T_min = 0.770, T_max = 1.000	k = −14→15
7361 measured reflections	l = −14→12

Refinement top

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(F_o²) + (0.059P)² + 0.2398P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.114	(Δ/σ)_max = 0.001
S = 1.04	Δρ_max = 0.25 e Å⁻³
2249 reflections	Δρ_min = −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)

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O3^iv	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···O1^v	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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