Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 2| February 2014| Page o115
doi:10.1107/S1600536813035009

N′-[(1E)-1-(2-Fluoro­phen­yl)ethyl­­idene]pyridine-3-carbohydrazide

P. B. Sreeja,a M. Sithambaresan,b* N. Aiswaryac and M. R. Prathapachandra Kurupc

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

(Received 4 December 2013; accepted 31 December 2013; online 8 January 2014)

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 hydrazones, see: Sreeja et al. (2004[Sreeja, P. B., Kurup, M. R. P., Kishore, A. & Jasmin, C. (2004). Polyhedron, 23, 575-581.]); Ajani et al. (2010[Ajani, O. O., Obafemi, C. A., Nwinyi, O. C. & Akinpelu, D. A. (2010). Bioorg. Med. Chem. 18, 214-221.]). For the synthesis of related compounds and for related work, see: Mangalam & Kurup (2011[Mangalam, N. A. & Kurup, M. R. P. (2011). Spectrochim. Acta Part A, 78, 926-934.]). For a related structure, see: Nair et al. (2012[Nair, Y., Sithambaresan, M. & Kurup, M. R. P. (2012). Acta Cryst. E68, o2709.]). For di­fluoro­phenyl compounds, see: Nayak et al. (2012[Nayak, S. K., Reddy, M. K., Chopra, D. & Guru Row, T. N. (2012). CrystEngComm. 14, 200-210.]).

[Scheme 1]

Experimental

Crystal data

  • C14H12FN3O

  • Mr = 257.27

  • Orthorhombic, P b c n

  • a = 18.926 (3) Å

  • b = 8.0486 (9) Å

  • c = 16.337 (3) Å

  • V = 2488.6 (7) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 296 K

  • 0.50 × 0.25 × 0.20 mm
Data collection

  • Bruker ApexII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, SADABS and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.952, Tmax = 0.980

  • 19111 measured reflections

  • 3009 independent reflections

  • 1755 reflections with I > 2σ(I)

  • Rint = 0.056
Refinement

  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 0.161

  • S = 1.01

  • 2999 reflections

  • 188 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

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+{\script{1\over 2}}, y-{\script{1\over 2}}, z].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, SADABS and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, SADABS and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, SADABS and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

CCDC reference: 979240

Crystal structure: contains datablocks Global, I. DOI: 10.1107/S1600536813035009/zl2571sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813035009/zl2571Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813035009/zl2571Isup3.cml

checkCIF report


Comment top

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).

Related literature top

For biological properties of hydrazones, 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).

Experimental top

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).

Refinement top

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).

Structure description top

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).

For biological properties of hydrazones, 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).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. ORTEP diagram of N'-[(1E)-1-(2-fluorophenyl)ethylidene]pyridine-3-carbohydrazide with 50% probability ellipsoids. Disordered hydrogen atoms H2 and H6 were omitted for clarity.
[Figure 2] Fig. 2. Bifurcated hydrogen-bonding interactions creating a chain propagating along the b-axis, and C—H···F interactions.
N'-[(1E)-1-(2-Fluorophenyl)ethylidene]pyridine-3-carbohydrazide top
Crystal data top
C14H12FN3OF(000) = 1072
Mr = 257.27Dx = 1.373 Mg m−3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 2433 reflections
a = 18.926 (3) Åθ = 2.5–22.6°
b = 8.0486 (9) ŵ = 0.10 mm−1
c = 16.337 (3) ÅT = 296 K
V = 2488.6 (7) Å3Needle, colourless
Z = 80.50 × 0.25 × 0.20 mm
Data collection top
Bruker ApexII CCD
diffractometer		3009 independent reflections
Radiation source: fine-focus sealed tube1755 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
Detector resolution: 8.33 pixels mm-1θmax = 28.0°, θmin = 2.5°
ω and φ scanh = −24→25
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		k = −10→10
Tmin = 0.952, Tmax = 0.980l = −21→21
19111 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H 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 reflectionsΔρmax = 0.29 e Å−3
188 parametersΔρmin = −0.22 e Å−3
1 restraintExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0048 (13)
Crystal data top
C14H12FN3OV = 2488.6 (7) Å3
Mr = 257.27Z = 8
Orthorhombic, PbcnMo Kα radiation
a = 18.926 (3) ŵ = 0.10 mm−1
b = 8.0486 (9) ÅT = 296 K
c = 16.337 (3) Å0.50 × 0.25 × 0.20 mm
Data collection top
Bruker ApexII CCD
diffractometer		3009 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		1755 reflections with I > 2σ(I)
Tmin = 0.952, Tmax = 0.980Rint = 0.056
19111 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0511 restraint
wR(F2) = 0.161H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.29 e Å−3
2999 reflectionsΔρmin = −0.22 e Å−3
188 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.16369 (8)1.08491 (17)0.92895 (10)0.0564 (5)
N10.28297 (9)1.04304 (17)1.01301 (10)0.0379 (4)
N20.25250 (9)0.91485 (18)0.96943 (10)0.0384 (4)
N30.05671 (13)0.6619 (3)0.84194 (16)0.0827 (8)
F10.26405 (10)1.2489 (2)1.14815 (13)0.0557 (7)0.632 (4)
F1B0.4820 (2)1.1072 (5)1.0493 (3)0.0761 (16)0.368 (4)
C60.44269 (12)1.1919 (3)1.09238 (15)0.0533 (6)
H60.47191.11801.06460.064*0.632 (4)
C20.33059 (12)1.2728 (2)1.13857 (13)0.0447 (5)
H20.28221.25481.14300.054*0.368 (4)
C50.47260 (14)1.3288 (3)1.12899 (17)0.0672 (7)
H50.52111.34661.12590.081*
C40.43039 (15)1.4381 (3)1.16994 (18)0.0717 (8)
H40.45011.53171.19430.086*
C30.35920 (15)1.4110 (3)1.17547 (16)0.0628 (7)
H30.33051.48501.20380.075*
C10.37091 (10)1.1596 (2)1.09523 (12)0.0378 (5)
C70.33978 (10)1.0136 (2)1.05237 (12)0.0371 (4)
C80.37763 (12)0.8504 (2)1.05763 (16)0.0551 (6)
H8A0.34410.76351.06810.083*
H8B0.41160.85441.10130.083*
H8C0.40150.82891.00690.083*
C90.19212 (11)0.9487 (2)0.92867 (12)0.0386 (5)
C100.16141 (11)0.8085 (2)0.88031 (11)0.0374 (5)
C110.08970 (12)0.7822 (3)0.88351 (15)0.0545 (6)
H110.06260.85190.91640.065*
C120.09829 (18)0.5653 (4)0.79477 (19)0.0829 (9)
H120.07690.47950.76580.099*
C130.16935 (14)0.5845 (3)0.78654 (15)0.0601 (6)
H130.19540.51550.75220.072*
C140.20124 (11)0.7080 (2)0.83009 (13)0.0460 (5)
H140.24980.72420.82590.055*
H2'0.2692 (10)0.8137 (15)0.9722 (14)0.051 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0594 (10)0.0345 (8)0.0752 (12)0.0116 (7)−0.0128 (8)−0.0112 (7)
N10.0495 (10)0.0247 (7)0.0393 (9)−0.0057 (7)−0.0023 (8)−0.0022 (6)
N20.0499 (10)0.0222 (7)0.0431 (9)−0.0004 (7)−0.0070 (8)−0.0031 (6)
N30.0724 (15)0.0924 (17)0.0834 (18)−0.0245 (13)−0.0065 (13)−0.0225 (14)
F10.0434 (13)0.0599 (13)0.0639 (14)0.0009 (9)0.0058 (9)−0.0186 (10)
F1B0.053 (2)0.072 (3)0.103 (3)−0.0039 (19)0.026 (2)−0.023 (2)
C60.0507 (13)0.0508 (13)0.0583 (14)−0.0085 (11)0.0020 (11)−0.0027 (11)
C20.0508 (13)0.0406 (11)0.0426 (11)0.0015 (9)−0.0056 (10)−0.0032 (8)
C50.0579 (15)0.0559 (14)0.088 (2)−0.0180 (12)−0.0146 (14)−0.0041 (13)
C40.0798 (19)0.0495 (14)0.086 (2)−0.0141 (13)−0.0316 (16)−0.0113 (13)
C30.0851 (19)0.0412 (12)0.0621 (15)0.0095 (12)−0.0157 (13)−0.0182 (11)
C10.0479 (12)0.0306 (9)0.0347 (10)−0.0059 (8)−0.0019 (9)0.0009 (7)
C70.0423 (11)0.0307 (9)0.0384 (10)−0.0041 (8)0.0034 (9)−0.0009 (7)
C80.0528 (13)0.0374 (11)0.0751 (16)0.0050 (10)−0.0097 (12)−0.0117 (10)
C90.0479 (11)0.0262 (9)0.0417 (11)−0.0001 (8)−0.0002 (9)−0.0021 (7)
C100.0449 (11)0.0305 (9)0.0368 (10)0.0001 (8)−0.0059 (8)0.0018 (7)
C110.0489 (13)0.0561 (13)0.0584 (15)−0.0020 (11)−0.0031 (11)−0.0108 (11)
C120.106 (2)0.0739 (18)0.0687 (18)−0.0330 (18)−0.0120 (17)−0.0239 (15)
C130.0832 (18)0.0477 (12)0.0492 (13)−0.0034 (12)0.0003 (12)−0.0194 (10)
C140.0496 (12)0.0428 (11)0.0457 (12)−0.0013 (9)−0.0019 (10)−0.0070 (9)
Geometric parameters (Å, º) top
O1—C91.221 (2)C4—C31.368 (4)
N1—C71.275 (2)C4—H40.9300
N1—N21.380 (2)C3—H30.9300
N2—C91.350 (3)C1—C71.490 (3)
N2—H2'0.875 (9)C7—C81.498 (3)
N3—C111.338 (3)C8—H8A0.9600
N3—C121.348 (4)C8—H8B0.9600
F1—C21.284 (3)C8—H8C0.9600
F1B—C61.230 (4)C9—C101.495 (3)
C6—C51.376 (3)C10—C111.375 (3)
C6—C11.384 (3)C10—C141.377 (3)
C6—H60.9300C11—H110.9300
C2—C31.376 (3)C12—C131.360 (4)
C2—C11.383 (3)C12—H120.9300
C2—H20.9300C13—C141.363 (3)
C5—C41.364 (4)C13—H130.9300
C5—H50.9300C14—H140.9300
C7—N1—N2118.26 (15)C6—C1—C7121.36 (18)
C9—N2—N1117.22 (15)N1—C7—C1115.06 (16)
C9—N2—H2'121.3 (14)N1—C7—C8126.53 (17)
N1—N2—H2'121.2 (14)C1—C7—C8118.40 (17)
C11—N3—C12115.8 (2)C7—C8—H8A109.5
F1B—C6—C5116.3 (3)C7—C8—H8B109.5
F1B—C6—C1120.6 (3)H8A—C8—H8B109.5
C5—C6—C1122.7 (2)C7—C8—H8C109.5
F1B—C6—H66.8H8A—C8—H8C109.5
C5—C6—H6118.7H8B—C8—H8C109.5
C1—C6—H6118.7O1—C9—N2123.50 (17)
F1—C2—C3117.0 (2)O1—C9—C10120.55 (18)
F1—C2—C1120.32 (19)N2—C9—C10115.94 (15)
C3—C2—C1122.6 (2)C11—C10—C14118.21 (19)
F1—C2—H22.6C11—C10—C9118.68 (18)
C3—C2—H2118.7C14—C10—C9123.06 (18)
C1—C2—H2118.7N3—C11—C10123.6 (2)
C4—C5—C6119.3 (2)N3—C11—H11118.2
C4—C5—H5120.4C10—C11—H11118.2
C6—C5—H5120.4N3—C12—C13124.6 (2)
C5—C4—C3120.4 (2)N3—C12—H12117.7
C5—C4—H4119.8C13—C12—H12117.7
C3—C4—H4119.8C12—C13—C14118.0 (2)
C4—C3—C2119.2 (2)C12—C13—H13121.0
C4—C3—H3120.4C14—C13—H13121.0
C2—C3—H3120.4C13—C14—C10119.8 (2)
C2—C1—C6115.79 (18)C13—C14—H14120.1
C2—C1—C7122.84 (18)C10—C14—H14120.1
C7—N1—N2—C9179.58 (18)C6—C1—C7—N1−135.9 (2)
F1B—C6—C5—C4172.7 (4)C2—C1—C7—C8−138.5 (2)
C1—C6—C5—C40.0 (4)C6—C1—C7—C842.9 (3)
C6—C5—C4—C30.8 (4)N1—N2—C9—O1−0.3 (3)
C5—C4—C3—C2−0.6 (4)N1—N2—C9—C10178.48 (16)
F1—C2—C3—C4177.3 (2)O1—C9—C10—C11−44.3 (3)
C1—C2—C3—C4−0.5 (4)N2—C9—C10—C11136.9 (2)
F1—C2—C1—C6−176.5 (2)O1—C9—C10—C14133.2 (2)
C3—C2—C1—C61.2 (3)N2—C9—C10—C14−45.7 (3)
F1—C2—C1—C74.8 (3)C12—N3—C11—C10−0.5 (4)
C3—C2—C1—C7−177.5 (2)C14—C10—C11—N31.6 (3)
F1B—C6—C1—C2−173.4 (3)C9—C10—C11—N3179.1 (2)
C5—C6—C1—C2−1.0 (3)C11—N3—C12—C13−1.0 (5)
F1B—C6—C1—C75.3 (4)N3—C12—C13—C141.3 (5)
C5—C6—C1—C7177.7 (2)C12—C13—C14—C10−0.1 (4)
N2—N1—C7—C1177.76 (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—N142.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2′···O1i0.88 (1)2.35 (1)3.163 (2)156 (2)
N2—H2′···N1i0.88 (1)2.48 (2)3.148 (2)133 (2)
Symmetry code: (i) −x+1/2, y−1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2'···O1i0.875 (9)2.346 (13)3.163 (2)156 (2)
N2—H2'···N1i0.875 (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

First citationAjani, 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
 First citationBrandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2004). APEX2, SAINT, SADABS and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationMangalam, N. A. & Kurup, M. R. P. (2011). Spectrochim. Acta Part A, 78, 926–934.  Web of Science CSD CrossRef Google Scholar
 First citationNair, Y., Sithambaresan, M. & Kurup, M. R. P. (2012). Acta Cryst. E68, o2709.  CSD CrossRef IUCr Journals Google Scholar
 First citationNayak, S. K., Reddy, M. K., Chopra, D. & Guru Row, T. N. (2012). CrystEngComm. 14, 200–210.  Web of Science CSD CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSreeja, P. B., Kurup, M. R. P., Kishore, A. & Jasmin, C. (2004). Polyhedron, 23, 575–581.  Web of Science CSD CrossRef CAS Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 2| February 2014| Page o115
doi:10.1107/S1600536813035009
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS