organic compounds
N′-[(1E)-1-(2-Fluorophenyl)ethylidene]pyridine-3-carbohydrazide
aDepartment of Chemistry, Christ University, Hosur Road, Bangalore 560 029, Karnataka, India, bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka, and cDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India
*Correspondence e-mail: eesans@yahoo.com
The title compound, C14H12FN3O, adopts an E conformation with respect to the azomethine double bond whereas the N and methyl C atoms are in a Z conformation with respect to the same bond. The ketonic O and azomethine N atoms are cis to each other. The non-planar molecule [the dihedral angle between the benzene rings is 7.44 (11)°] exists in an amido form with a C=O bond length of 1.221 (2) Å. In the crystal, a bifurcated N—H⋯(O,N) hydrogen bond is formed between the amide H atom and the keto O and imine N atoms of an adjacent molecule, leading to the formation of chains propagating along the b-axis direction. Through a 180° rotation of the fluorophenyl ring, the F atom is disordered over two sites with an occupancy ratio of 0.632 (4):0.368 (4).
CCDC reference: 979240
Related literature
For biological properties of et al. (2004); Ajani et al. (2010). For the synthesis of related compounds and for related work, see: Mangalam & Kurup (2011). For a related structure, see: Nair et al. (2012). For difluorophenyl compounds, see: Nayak et al. (2012).
see: SreejaExperimental
Crystal data
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Data collection: APEX2 (Bruker, 2004); cell APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010).
Supporting information
CCDC reference: 979240
10.1107/S1600536813035009/zl2571sup1.cif
contains datablocks Global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813035009/zl2571Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813035009/zl2571Isup3.cml
The title compound was prepared by adapting a reported procedure (Mangalam & Kurup, 2011). Methanolic solutions of nicotinic acid hydrazide (0.137 g, 1 mmol) and 2-fluoroacetophenone (0.138 g, 1 mmol) were combined, a few drops of glacial acetic acid were added, and the mixture was heated to reflux for 6 h. On cooling the mixture, crystals of the hydrazone separated out. The crystals were filtered off, washed with a minimum quantity of methanol and dried over P4O10 in vacuo. Crystals suitable for X-ray analysis were obtained in 80% yield (0.2048 g) from methanolic solution by slow evaporation. The melting point of the prepared compound was found to be 186 °C.
IR (KBr, υ in cm-1): 3269, 3058, 2858, 1673, 1621, 1539, 1487, 1356, 1273, 1179, 1121, 1063, 943, 799, 709, 651, 565, 513. 1H NMR (400 MHz, CDCl3, δ, p.p.m.): 10.95 (s, 1H), 7.26—9.03 (m, 9H), 2.36 (s, 3H).
The disordered fluorine atoms F1 and F1B were refined freely, with the sum of their occupancy factors constrained to 1.0. Disordered hydrogen atoms H2 and H6 were placed in geometrically idealized positions and were constrained to ride on their parent C atoms with C–H distances of 0.93 Å. The N2—H2' distance was restrained to 0.88 (1) Å. The remaining H atoms were placed in calculated positions, guided by difference maps, with C–H bond distances 0.93–0.96 Å. H atoms were assigned as Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(methyl C). Omitted owing to bad disagreement were the reflections (2 2 3), (5 2 1) and (2 0 0).
Hydrazones and their derivatives remain in the limelight of research due to the biological properties that many of them possess (Sreeja et al., 2004; Ajani et al., 2010). As a continuation of our work in this area (Mangalam & Kurup, 2011), we herein report a new aroyl hydrazone, derived from the reaction of 2-fluoroacetophenone and nicotinic acid hydrazide.
The molecule crystallizes in orthorhombic
Pbcn. The title compound adopts an E configuration with respect to the azomethine olefinic bond whilst the C8 and N2 atoms are in Z configuration with respect to the same bond with torsion angles for C1–C7–N1–N2 and N2–N1–C7–C8 of 177.76 (16) and -0.9 (3)°, respectively (Fig. 1). The ketonic O and the azomethine N are cis to each other with a torsion angle of -0.3 (3)°. The molecule exists in the amido form with a C9=O1 bond length of 1.221 (2) Å which is very close to the reported C=O bond length in a similar structure (Nair et al., 2012). The pyridyl and fluorophenyl rings make dihedral angles of 45.44 (7) and 42.48 (6)° with the C(=O)N2CC central unit making the molecule non-planar.A bifurcated hydrogen bond is formed between the amide H atom and the keto oxygen, O1 and imine nitrogen atom, N1 of an adjacent molecule which leads to formation of a hydrogen bonded chains of molecules that propagate along the b-axis direction of the structure (Fig. 2) with donor-acceptor distances of 3.163 (2) Å and 3.148 (2) Å respectively. In addition to the above intermolecular H bonding interactions, a non-classical H bond between H8A of methyl carbon C8 and the fluorine (F1) atom also stabilizes the packing. The non-classical H bonding features a C8···F1 distance of 3.169 (3) Å and links the molecules in a zigzag fashion (Fig. 2). No significant π···π interactions with centroid-centroid distances of less than 4 Å are observed in the structure.
Through a 180° rotation of the fluorophenyl ring, the fluorine atom F1 is disordered over two sites in a ratio of 63.3 (4):36.7 (4). Similar instances of positional disorder had been previously reported (Nayak et al., 2012).
For biological properties of
see: Sreeja et al. (2004); Ajani et al. (2010). For the synthesis of related compounds and for related work, see: Mangalam & Kurup (2011). For a related structure, see: Nair et al. (2012). For difluorophenyl compounds, see: Nayak et al. (2012).Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).C14H12FN3O | F(000) = 1072 |
Mr = 257.27 | Dx = 1.373 Mg m−3 |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 2433 reflections |
a = 18.926 (3) Å | θ = 2.5–22.6° |
b = 8.0486 (9) Å | µ = 0.10 mm−1 |
c = 16.337 (3) Å | T = 296 K |
V = 2488.6 (7) Å3 | Needle, colourless |
Z = 8 | 0.50 × 0.25 × 0.20 mm |
Bruker ApexII CCD diffractometer | 3009 independent reflections |
Radiation source: fine-focus sealed tube | 1755 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.0°, θmin = 2.5° |
ω and φ scan | h = −24→25 |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | k = −10→10 |
Tmin = 0.952, Tmax = 0.980 | l = −21→21 |
19111 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.161 | w = 1/[σ2(Fo2) + (0.0806P)2 + 0.3159P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
2999 reflections | Δρmax = 0.29 e Å−3 |
188 parameters | Δρmin = −0.22 e Å−3 |
1 restraint | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0048 (13) |
C14H12FN3O | V = 2488.6 (7) Å3 |
Mr = 257.27 | Z = 8 |
Orthorhombic, Pbcn | Mo Kα radiation |
a = 18.926 (3) Å | µ = 0.10 mm−1 |
b = 8.0486 (9) Å | T = 296 K |
c = 16.337 (3) Å | 0.50 × 0.25 × 0.20 mm |
Bruker ApexII CCD diffractometer | 3009 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 1755 reflections with I > 2σ(I) |
Tmin = 0.952, Tmax = 0.980 | Rint = 0.056 |
19111 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 1 restraint |
wR(F2) = 0.161 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.29 e Å−3 |
2999 reflections | Δρmin = −0.22 e Å−3 |
188 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 > 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.16369 (8) | 1.08491 (17) | 0.92895 (10) | 0.0564 (5) | |
N1 | 0.28297 (9) | 1.04304 (17) | 1.01301 (10) | 0.0379 (4) | |
N2 | 0.25250 (9) | 0.91485 (18) | 0.96943 (10) | 0.0384 (4) | |
N3 | 0.05671 (13) | 0.6619 (3) | 0.84194 (16) | 0.0827 (8) | |
F1 | 0.26405 (10) | 1.2489 (2) | 1.14815 (13) | 0.0557 (7) | 0.632 (4) |
F1B | 0.4820 (2) | 1.1072 (5) | 1.0493 (3) | 0.0761 (16) | 0.368 (4) |
C6 | 0.44269 (12) | 1.1919 (3) | 1.09238 (15) | 0.0533 (6) | |
H6 | 0.4719 | 1.1180 | 1.0646 | 0.064* | 0.632 (4) |
C2 | 0.33059 (12) | 1.2728 (2) | 1.13857 (13) | 0.0447 (5) | |
H2 | 0.2822 | 1.2548 | 1.1430 | 0.054* | 0.368 (4) |
C5 | 0.47260 (14) | 1.3288 (3) | 1.12899 (17) | 0.0672 (7) | |
H5 | 0.5211 | 1.3466 | 1.1259 | 0.081* | |
C4 | 0.43039 (15) | 1.4381 (3) | 1.16994 (18) | 0.0717 (8) | |
H4 | 0.4501 | 1.5317 | 1.1943 | 0.086* | |
C3 | 0.35920 (15) | 1.4110 (3) | 1.17547 (16) | 0.0628 (7) | |
H3 | 0.3305 | 1.4850 | 1.2038 | 0.075* | |
C1 | 0.37091 (10) | 1.1596 (2) | 1.09523 (12) | 0.0378 (5) | |
C7 | 0.33978 (10) | 1.0136 (2) | 1.05237 (12) | 0.0371 (4) | |
C8 | 0.37763 (12) | 0.8504 (2) | 1.05763 (16) | 0.0551 (6) | |
H8A | 0.3441 | 0.7635 | 1.0681 | 0.083* | |
H8B | 0.4116 | 0.8544 | 1.1013 | 0.083* | |
H8C | 0.4015 | 0.8289 | 1.0069 | 0.083* | |
C9 | 0.19212 (11) | 0.9487 (2) | 0.92867 (12) | 0.0386 (5) | |
C10 | 0.16141 (11) | 0.8085 (2) | 0.88031 (11) | 0.0374 (5) | |
C11 | 0.08970 (12) | 0.7822 (3) | 0.88351 (15) | 0.0545 (6) | |
H11 | 0.0626 | 0.8519 | 0.9164 | 0.065* | |
C12 | 0.09829 (18) | 0.5653 (4) | 0.79477 (19) | 0.0829 (9) | |
H12 | 0.0769 | 0.4795 | 0.7658 | 0.099* | |
C13 | 0.16935 (14) | 0.5845 (3) | 0.78654 (15) | 0.0601 (6) | |
H13 | 0.1954 | 0.5155 | 0.7522 | 0.072* | |
C14 | 0.20124 (11) | 0.7080 (2) | 0.83009 (13) | 0.0460 (5) | |
H14 | 0.2498 | 0.7242 | 0.8259 | 0.055* | |
H2' | 0.2692 (10) | 0.8137 (15) | 0.9722 (14) | 0.051 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0594 (10) | 0.0345 (8) | 0.0752 (12) | 0.0116 (7) | −0.0128 (8) | −0.0112 (7) |
N1 | 0.0495 (10) | 0.0247 (7) | 0.0393 (9) | −0.0057 (7) | −0.0023 (8) | −0.0022 (6) |
N2 | 0.0499 (10) | 0.0222 (7) | 0.0431 (9) | −0.0004 (7) | −0.0070 (8) | −0.0031 (6) |
N3 | 0.0724 (15) | 0.0924 (17) | 0.0834 (18) | −0.0245 (13) | −0.0065 (13) | −0.0225 (14) |
F1 | 0.0434 (13) | 0.0599 (13) | 0.0639 (14) | 0.0009 (9) | 0.0058 (9) | −0.0186 (10) |
F1B | 0.053 (2) | 0.072 (3) | 0.103 (3) | −0.0039 (19) | 0.026 (2) | −0.023 (2) |
C6 | 0.0507 (13) | 0.0508 (13) | 0.0583 (14) | −0.0085 (11) | 0.0020 (11) | −0.0027 (11) |
C2 | 0.0508 (13) | 0.0406 (11) | 0.0426 (11) | 0.0015 (9) | −0.0056 (10) | −0.0032 (8) |
C5 | 0.0579 (15) | 0.0559 (14) | 0.088 (2) | −0.0180 (12) | −0.0146 (14) | −0.0041 (13) |
C4 | 0.0798 (19) | 0.0495 (14) | 0.086 (2) | −0.0141 (13) | −0.0316 (16) | −0.0113 (13) |
C3 | 0.0851 (19) | 0.0412 (12) | 0.0621 (15) | 0.0095 (12) | −0.0157 (13) | −0.0182 (11) |
C1 | 0.0479 (12) | 0.0306 (9) | 0.0347 (10) | −0.0059 (8) | −0.0019 (9) | 0.0009 (7) |
C7 | 0.0423 (11) | 0.0307 (9) | 0.0384 (10) | −0.0041 (8) | 0.0034 (9) | −0.0009 (7) |
C8 | 0.0528 (13) | 0.0374 (11) | 0.0751 (16) | 0.0050 (10) | −0.0097 (12) | −0.0117 (10) |
C9 | 0.0479 (11) | 0.0262 (9) | 0.0417 (11) | −0.0001 (8) | −0.0002 (9) | −0.0021 (7) |
C10 | 0.0449 (11) | 0.0305 (9) | 0.0368 (10) | 0.0001 (8) | −0.0059 (8) | 0.0018 (7) |
C11 | 0.0489 (13) | 0.0561 (13) | 0.0584 (15) | −0.0020 (11) | −0.0031 (11) | −0.0108 (11) |
C12 | 0.106 (2) | 0.0739 (18) | 0.0687 (18) | −0.0330 (18) | −0.0120 (17) | −0.0239 (15) |
C13 | 0.0832 (18) | 0.0477 (12) | 0.0492 (13) | −0.0034 (12) | 0.0003 (12) | −0.0194 (10) |
C14 | 0.0496 (12) | 0.0428 (11) | 0.0457 (12) | −0.0013 (9) | −0.0019 (10) | −0.0070 (9) |
O1—C9 | 1.221 (2) | C4—C3 | 1.368 (4) |
N1—C7 | 1.275 (2) | C4—H4 | 0.9300 |
N1—N2 | 1.380 (2) | C3—H3 | 0.9300 |
N2—C9 | 1.350 (3) | C1—C7 | 1.490 (3) |
N2—H2' | 0.875 (9) | C7—C8 | 1.498 (3) |
N3—C11 | 1.338 (3) | C8—H8A | 0.9600 |
N3—C12 | 1.348 (4) | C8—H8B | 0.9600 |
F1—C2 | 1.284 (3) | C8—H8C | 0.9600 |
F1B—C6 | 1.230 (4) | C9—C10 | 1.495 (3) |
C6—C5 | 1.376 (3) | C10—C11 | 1.375 (3) |
C6—C1 | 1.384 (3) | C10—C14 | 1.377 (3) |
C6—H6 | 0.9300 | C11—H11 | 0.9300 |
C2—C3 | 1.376 (3) | C12—C13 | 1.360 (4) |
C2—C1 | 1.383 (3) | C12—H12 | 0.9300 |
C2—H2 | 0.9300 | C13—C14 | 1.363 (3) |
C5—C4 | 1.364 (4) | C13—H13 | 0.9300 |
C5—H5 | 0.9300 | C14—H14 | 0.9300 |
C7—N1—N2 | 118.26 (15) | C6—C1—C7 | 121.36 (18) |
C9—N2—N1 | 117.22 (15) | N1—C7—C1 | 115.06 (16) |
C9—N2—H2' | 121.3 (14) | N1—C7—C8 | 126.53 (17) |
N1—N2—H2' | 121.2 (14) | C1—C7—C8 | 118.40 (17) |
C11—N3—C12 | 115.8 (2) | C7—C8—H8A | 109.5 |
F1B—C6—C5 | 116.3 (3) | C7—C8—H8B | 109.5 |
F1B—C6—C1 | 120.6 (3) | H8A—C8—H8B | 109.5 |
C5—C6—C1 | 122.7 (2) | C7—C8—H8C | 109.5 |
F1B—C6—H6 | 6.8 | H8A—C8—H8C | 109.5 |
C5—C6—H6 | 118.7 | H8B—C8—H8C | 109.5 |
C1—C6—H6 | 118.7 | O1—C9—N2 | 123.50 (17) |
F1—C2—C3 | 117.0 (2) | O1—C9—C10 | 120.55 (18) |
F1—C2—C1 | 120.32 (19) | N2—C9—C10 | 115.94 (15) |
C3—C2—C1 | 122.6 (2) | C11—C10—C14 | 118.21 (19) |
F1—C2—H2 | 2.6 | C11—C10—C9 | 118.68 (18) |
C3—C2—H2 | 118.7 | C14—C10—C9 | 123.06 (18) |
C1—C2—H2 | 118.7 | N3—C11—C10 | 123.6 (2) |
C4—C5—C6 | 119.3 (2) | N3—C11—H11 | 118.2 |
C4—C5—H5 | 120.4 | C10—C11—H11 | 118.2 |
C6—C5—H5 | 120.4 | N3—C12—C13 | 124.6 (2) |
C5—C4—C3 | 120.4 (2) | N3—C12—H12 | 117.7 |
C5—C4—H4 | 119.8 | C13—C12—H12 | 117.7 |
C3—C4—H4 | 119.8 | C12—C13—C14 | 118.0 (2) |
C4—C3—C2 | 119.2 (2) | C12—C13—H13 | 121.0 |
C4—C3—H3 | 120.4 | C14—C13—H13 | 121.0 |
C2—C3—H3 | 120.4 | C13—C14—C10 | 119.8 (2) |
C2—C1—C6 | 115.79 (18) | C13—C14—H14 | 120.1 |
C2—C1—C7 | 122.84 (18) | C10—C14—H14 | 120.1 |
C7—N1—N2—C9 | 179.58 (18) | C6—C1—C7—N1 | −135.9 (2) |
F1B—C6—C5—C4 | 172.7 (4) | C2—C1—C7—C8 | −138.5 (2) |
C1—C6—C5—C4 | 0.0 (4) | C6—C1—C7—C8 | 42.9 (3) |
C6—C5—C4—C3 | 0.8 (4) | N1—N2—C9—O1 | −0.3 (3) |
C5—C4—C3—C2 | −0.6 (4) | N1—N2—C9—C10 | 178.48 (16) |
F1—C2—C3—C4 | 177.3 (2) | O1—C9—C10—C11 | −44.3 (3) |
C1—C2—C3—C4 | −0.5 (4) | N2—C9—C10—C11 | 136.9 (2) |
F1—C2—C1—C6 | −176.5 (2) | O1—C9—C10—C14 | 133.2 (2) |
C3—C2—C1—C6 | 1.2 (3) | N2—C9—C10—C14 | −45.7 (3) |
F1—C2—C1—C7 | 4.8 (3) | C12—N3—C11—C10 | −0.5 (4) |
C3—C2—C1—C7 | −177.5 (2) | C14—C10—C11—N3 | 1.6 (3) |
F1B—C6—C1—C2 | −173.4 (3) | C9—C10—C11—N3 | 179.1 (2) |
C5—C6—C1—C2 | −1.0 (3) | C11—N3—C12—C13 | −1.0 (5) |
F1B—C6—C1—C7 | 5.3 (4) | N3—C12—C13—C14 | 1.3 (5) |
C5—C6—C1—C7 | 177.7 (2) | C12—C13—C14—C10 | −0.1 (4) |
N2—N1—C7—C1 | 177.76 (16) | C11—C10—C14—C13 | −1.2 (3) |
N2—N1—C7—C8 | −0.9 (3) | C9—C10—C14—C13 | −178.7 (2) |
C2—C1—C7—N1 | 42.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2′···O1i | 0.88 (1) | 2.35 (1) | 3.163 (2) | 156 (2) |
N2—H2′···N1i | 0.88 (1) | 2.48 (2) | 3.148 (2) | 133 (2) |
Symmetry code: (i) −x+1/2, y−1/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2'···O1i | 0.875 (9) | 2.346 (13) | 3.163 (2) | 156 (2) |
N2—H2'···N1i | 0.875 (9) | 2.483 (17) | 3.148 (2) | 133.4 (17) |
Symmetry code: (i) −x+1/2, y−1/2, z. |
Acknowledgements
PBS is thankful to the Center for Research, Christ University, for financial assistance. NA thanks the University Grants Commission (India) for a Junior Research Fellowship. MRPK thanks the University Grants Commission, New Delhi, for a UGC–BSR one-time grant to faculty. The authors thank the Sophisticated Analytical Instruments Facility, Cochin University of Science & Technology, for the data collection.
References
Ajani, O. O., Obafemi, C. A., Nwinyi, O. C. & Akinpelu, D. A. (2010). Bioorg. Med. Chem. 18, 214–221. Web of Science CrossRef PubMed CAS Google Scholar
Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2004). APEX2, SAINT, SADABS and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Mangalam, N. A. & Kurup, M. R. P. (2011). Spectrochim. Acta Part A, 78, 926–934. Web of Science CSD CrossRef Google Scholar
Nair, Y., Sithambaresan, M. & Kurup, M. R. P. (2012). Acta Cryst. E68, o2709. CSD CrossRef IUCr Journals Google Scholar
Nayak, S. K., Reddy, M. K., Chopra, D. & Guru Row, T. N. (2012). CrystEngComm. 14, 200–210. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sreeja, P. B., Kurup, M. R. P., Kishore, A. & Jasmin, C. (2004). Polyhedron, 23, 575–581. Web of Science CSD CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Hydrazones and their derivatives remain in the limelight of research due to the biological properties that many of them possess (Sreeja et al., 2004; Ajani et al., 2010). As a continuation of our work in this area (Mangalam & Kurup, 2011), we herein report a new aroyl hydrazone, derived from the reaction of 2-fluoroacetophenone and nicotinic acid hydrazide.
The molecule crystallizes in orthorhombic space group Pbcn. The title compound adopts an E configuration with respect to the azomethine olefinic bond whilst the C8 and N2 atoms are in Z configuration with respect to the same bond with torsion angles for C1–C7–N1–N2 and N2–N1–C7–C8 of 177.76 (16) and -0.9 (3)°, respectively (Fig. 1). The ketonic O and the azomethine N are cis to each other with a torsion angle of -0.3 (3)°. The molecule exists in the amido form with a C9=O1 bond length of 1.221 (2) Å which is very close to the reported C=O bond length in a similar structure (Nair et al., 2012). The pyridyl and fluorophenyl rings make dihedral angles of 45.44 (7) and 42.48 (6)° with the C(=O)N2CC central unit making the molecule non-planar.
A bifurcated hydrogen bond is formed between the amide H atom and the keto oxygen, O1 and imine nitrogen atom, N1 of an adjacent molecule which leads to formation of a hydrogen bonded chains of molecules that propagate along the b-axis direction of the structure (Fig. 2) with donor-acceptor distances of 3.163 (2) Å and 3.148 (2) Å respectively. In addition to the above intermolecular H bonding interactions, a non-classical H bond between H8A of methyl carbon C8 and the fluorine (F1) atom also stabilizes the packing. The non-classical H bonding features a C8···F1 distance of 3.169 (3) Å and links the molecules in a zigzag fashion (Fig. 2). No significant π···π interactions with centroid-centroid distances of less than 4 Å are observed in the structure.
Through a 180° rotation of the fluorophenyl ring, the fluorine atom F1 is disordered over two sites in a ratio of 63.3 (4):36.7 (4). Similar instances of positional disorder had been previously reported (Nayak et al., 2012).