Literature DB >> 24454252

N'-[(E)-2-Fluoro-benzyl-idene]benzo-hydrazide.

P B Sreeja1, M Sithambaresan2, N Aiswarya3, M R Prathapachandra Kurup3.   

Abstract

The asymmetric unit of the title compound, C14H11FN2O, contains two independent mol-ecules, both of which adopt the E conformation with respect to the azomethine C=N bond. The mol-ecules are non-planar, with dihedral angles of 26.92 (12) and 11.36 (11)° between the benzene and phenyl rings. In the crystal, mol-ecules are linked through N-H⋯O=C and N-H⋯N hydrogen bonds into chains along [101]. C-H⋯O contacts link these chains into layers parallel to (001). The three-dimensional crystal packing is stabilized by π-π inter-actions, the shortest separation between the centroids of benzene rings being 3.884 (1) Å.

Entities:  

Year:  2013        PMID: 24454252      PMCID: PMC3885076          DOI: 10.1107/S1600536813031747

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

For catalytic properties of hydrazones, see: Heravi et al. (2007 ▶). For their use as inhibitors of enzymes, see: Tamasi et al. (2005 ▶) and for their biological activity, see: Sreeja et al. (2004 ▶). For the synthesis of related compounds, see: Mangalam & Kurup (2011 ▶). For a related structure, see: Nair et al. (2012 ▶).

Experimental

Crystal data

C14H11FN2O M = 242.25 Monoclinic, a = 9.7010 (6) Å b = 17.4114 (13) Å c = 15.002 (1) Å β = 104.126 (4)° V = 2457.3 (3) Å3 Z = 8 Mo Kα radiation μ = 0.10 mm−1 T = 296 K 0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.968, T max = 0.977 18766 measured reflections 6111 independent reflections 3320 reflections with I > 2σ(I) R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.050 wR(F 2) = 0.165 S = 1.00 5972 reflections 333 parameters 2 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.21 e Å−3 Δρmin = −0.17 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 ▶). Crystal structure: contains datablock(s) Global, I. DOI: 10.1107/S1600536813031747/yk2100sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031747/yk2100Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813031747/yk2100Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C14H11FN2OF(000) = 1008
Mr = 242.25Dx = 1.310 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4473 reflections
a = 9.7010 (6) Åθ = 4.7–48.2°
b = 17.4114 (13) ŵ = 0.10 mm1
c = 15.002 (1) ÅT = 296 K
β = 104.126 (4)°Block, colourless
V = 2457.3 (3) Å30.35 × 0.30 × 0.25 mm
Z = 8
Bruker Kappa APEXII CCD area-detector diffractometer6111 independent reflections
Radiation source: fine-focus sealed tube3320 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 8.33 pixels mm-1θmax = 28.3°, θmin = 2.5°
ω and φ scanh = −12→11
Absorption correction: multi-scan (SADABS; Bruker, 2007)k = −23→17
Tmin = 0.968, Tmax = 0.977l = −19→19
18766 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165H atoms treated by a mixture of independent and constrained refinement
S = 1.00w = 1/[σ2(Fo2) + (0.0763P)2 + 0.4072P] where P = (Fo2 + 2Fc2)/3
5972 reflections(Δ/σ)max = 0.001
333 parametersΔρmax = 0.21 e Å3
2 restraintsΔρmin = −0.17 e Å3
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.
xyzUiso*/Ueq
F10.46744 (16)0.52151 (9)0.31008 (10)0.0961 (5)
F20.04425 (16)0.24110 (10)0.23115 (9)0.0973 (5)
O10.42500 (14)0.14776 (8)0.21005 (9)0.0613 (4)
O20.28675 (14)0.15829 (9)−0.13577 (9)0.0630 (4)
N10.44609 (15)0.29885 (10)0.23441 (10)0.0513 (4)
N20.54248 (16)0.24863 (9)0.28584 (10)0.0505 (4)
N30.16870 (15)0.19149 (9)0.00186 (10)0.0490 (4)
N40.30586 (16)0.16402 (10)0.01524 (11)0.0512 (4)
C10.3744 (2)0.50230 (12)0.23098 (15)0.0591 (5)
C20.2916 (3)0.55868 (13)0.18222 (19)0.0736 (6)
H20.30010.60920.20280.088*
C30.1957 (3)0.53942 (15)0.1024 (2)0.0862 (8)
H30.13820.57700.06800.103*
C40.1845 (3)0.46473 (16)0.07311 (19)0.0900 (8)
H40.11940.45170.01870.108*
C50.2685 (2)0.40901 (13)0.12344 (15)0.0706 (6)
H50.25950.35850.10260.085*
C60.36690 (19)0.42641 (11)0.20489 (13)0.0506 (5)
C70.46029 (19)0.36878 (12)0.25810 (13)0.0539 (5)
H70.53040.38320.30950.065*
C80.52872 (18)0.17362 (11)0.26640 (11)0.0464 (4)
C90.64558 (19)0.12175 (11)0.31359 (12)0.0490 (4)
C100.6233 (3)0.04460 (14)0.30166 (17)0.0771 (7)
H100.53510.02680.26890.093*
C110.7297 (3)−0.00725 (16)0.33747 (19)0.0953 (9)
H110.7136−0.05960.32800.114*
C120.8586 (3)0.01828 (16)0.38681 (18)0.0840 (8)
H120.9303−0.01660.41180.101*
C130.8819 (2)0.09439 (17)0.39922 (19)0.0865 (8)
H130.96990.11190.43270.104*
C140.7759 (2)0.14642 (14)0.36265 (16)0.0711 (6)
H140.79320.19880.37140.085*
C15−0.0531 (2)0.24951 (13)0.15067 (14)0.0599 (5)
C16−0.1862 (3)0.27441 (13)0.15287 (17)0.0698 (6)
H16−0.20830.28540.20840.084*
C17−0.2853 (2)0.28265 (13)0.07180 (19)0.0710 (6)
H17−0.37660.29900.07180.085*
C18−0.2513 (2)0.26703 (13)−0.00981 (16)0.0674 (6)
H18−0.31940.2730−0.06500.081*
C19−0.1169 (2)0.24265 (12)−0.01023 (14)0.0565 (5)
H19−0.09480.2323−0.06600.068*
C20−0.01365 (19)0.23326 (10)0.07091 (13)0.0488 (4)
C210.1288 (2)0.20552 (11)0.07427 (13)0.0514 (5)
H210.19200.19790.13110.062*
C220.35624 (18)0.14576 (10)−0.05743 (12)0.0461 (4)
C230.49959 (18)0.11042 (10)−0.03891 (12)0.0476 (4)
C240.5548 (2)0.09675 (15)−0.11316 (16)0.0715 (6)
H240.50390.1104−0.17190.086*
C250.6874 (3)0.06241 (17)−0.1000 (2)0.0918 (8)
H250.72440.0524−0.15050.110*
C260.7637 (3)0.04326 (15)−0.0146 (2)0.0873 (8)
H260.85310.0210−0.00670.105*
C270.7102 (2)0.05644 (14)0.05883 (18)0.0747 (7)
H270.76260.04330.11740.090*
C280.5777 (2)0.08945 (12)0.04711 (14)0.0604 (5)
H280.54060.09760.09790.073*
H4'0.3472 (19)0.1550 (11)0.0722 (7)0.060 (6)*
H2'0.6116 (18)0.2682 (12)0.3300 (12)0.077 (7)*
U11U22U33U12U13U23
F10.0962 (10)0.0799 (10)0.0961 (10)−0.0050 (8)−0.0077 (9)−0.0251 (8)
F20.0970 (10)0.1417 (14)0.0495 (7)0.0320 (9)0.0106 (7)−0.0092 (8)
O10.0577 (8)0.0644 (9)0.0510 (7)−0.0008 (6)−0.0076 (6)−0.0029 (6)
O20.0597 (8)0.0844 (11)0.0418 (7)0.0165 (7)0.0064 (6)0.0050 (7)
N10.0475 (9)0.0575 (11)0.0449 (8)0.0057 (7)0.0036 (7)0.0017 (7)
N20.0483 (9)0.0535 (10)0.0430 (8)0.0049 (7)−0.0015 (7)−0.0018 (7)
N30.0430 (8)0.0565 (10)0.0446 (8)0.0079 (7)0.0054 (7)−0.0006 (7)
N40.0448 (8)0.0657 (11)0.0392 (8)0.0139 (7)0.0027 (7)0.0006 (8)
C10.0513 (11)0.0597 (14)0.0664 (13)−0.0037 (9)0.0146 (10)−0.0060 (11)
C20.0728 (15)0.0510 (13)0.1003 (18)0.0042 (11)0.0276 (14)0.0002 (12)
C30.0769 (16)0.0693 (17)0.102 (2)0.0155 (13)0.0025 (15)0.0153 (15)
C40.0893 (18)0.0762 (18)0.0841 (17)0.0092 (14)−0.0184 (14)0.0068 (14)
C50.0721 (14)0.0571 (14)0.0712 (14)0.0045 (11)−0.0045 (12)0.0013 (11)
C60.0443 (10)0.0538 (12)0.0536 (11)0.0000 (8)0.0120 (8)0.0014 (9)
C70.0508 (11)0.0570 (13)0.0499 (11)0.0003 (9)0.0047 (8)−0.0034 (9)
C80.0449 (10)0.0579 (12)0.0339 (9)0.0026 (8)0.0049 (7)−0.0002 (8)
C90.0527 (11)0.0529 (12)0.0392 (9)0.0048 (8)0.0066 (8)0.0013 (8)
C100.0804 (16)0.0602 (15)0.0766 (15)0.0064 (11)−0.0081 (13)−0.0036 (12)
C110.115 (2)0.0582 (16)0.097 (2)0.0206 (14)−0.0042 (17)0.0005 (14)
C120.0837 (18)0.0819 (19)0.0815 (17)0.0333 (14)0.0107 (14)0.0127 (14)
C130.0576 (13)0.091 (2)0.0985 (19)0.0129 (13)−0.0052 (13)0.0154 (16)
C140.0556 (12)0.0655 (15)0.0806 (15)0.0029 (10)−0.0058 (11)0.0068 (12)
C150.0647 (13)0.0636 (13)0.0505 (11)0.0088 (10)0.0124 (10)−0.0022 (10)
C160.0799 (16)0.0693 (15)0.0690 (14)0.0092 (12)0.0351 (13)−0.0027 (11)
C170.0558 (13)0.0658 (15)0.0957 (18)0.0097 (10)0.0266 (13)0.0038 (13)
C180.0555 (12)0.0709 (15)0.0712 (14)0.0073 (10)0.0064 (11)0.0061 (12)
C190.0539 (11)0.0628 (13)0.0524 (11)0.0068 (9)0.0123 (9)0.0023 (10)
C200.0527 (11)0.0445 (11)0.0491 (10)0.0036 (8)0.0121 (9)−0.0005 (8)
C210.0500 (10)0.0604 (12)0.0407 (10)0.0085 (9)0.0052 (8)0.0004 (9)
C220.0465 (10)0.0460 (11)0.0436 (10)0.0009 (8)0.0070 (8)0.0003 (8)
C230.0442 (10)0.0446 (11)0.0535 (11)−0.0015 (8)0.0108 (8)−0.0041 (8)
C240.0652 (14)0.0886 (18)0.0640 (13)0.0070 (12)0.0222 (11)−0.0062 (12)
C250.0751 (17)0.112 (2)0.101 (2)0.0148 (15)0.0460 (16)−0.0117 (17)
C260.0539 (14)0.0893 (19)0.121 (2)0.0176 (12)0.0263 (15)0.0003 (17)
C270.0528 (12)0.0787 (16)0.0863 (17)0.0179 (11)0.0046 (12)0.0043 (13)
C280.0532 (11)0.0659 (14)0.0599 (12)0.0128 (10)0.0091 (10)0.0017 (10)
F1—C11.346 (2)C11—H110.9300
F2—C151.347 (2)C12—C131.350 (4)
O1—C81.231 (2)C12—H120.9300
O2—C221.223 (2)C13—C141.380 (3)
N1—C71.266 (2)C13—H130.9300
N1—N21.372 (2)C14—H140.9300
N2—C81.338 (2)C15—C161.370 (3)
N2—H2'0.887 (9)C15—C201.372 (3)
N3—C211.263 (2)C16—C171.362 (3)
N3—N41.382 (2)C16—H160.9300
N4—C221.337 (2)C17—C181.371 (3)
N4—H4'0.865 (9)C17—H170.9300
C1—C21.363 (3)C18—C191.373 (3)
C1—C61.375 (3)C18—H180.9300
C2—C31.367 (4)C19—C201.384 (3)
C2—H20.9300C19—H190.9300
C3—C41.368 (4)C20—C211.453 (3)
C3—H30.9300C21—H210.9300
C4—C51.370 (3)C22—C231.484 (2)
C4—H40.9300C23—C241.370 (3)
C5—C61.388 (3)C23—C281.377 (3)
C5—H50.9300C24—C251.388 (3)
C6—C71.453 (3)C24—H240.9300
C7—H70.9300C25—C261.356 (4)
C8—C91.487 (2)C25—H250.9300
C9—C101.365 (3)C26—C271.347 (4)
C9—C141.368 (3)C26—H260.9300
C10—C111.378 (3)C27—C281.380 (3)
C10—H100.9300C27—H270.9300
C11—C121.363 (4)C28—H280.9300
C7—N1—N2116.26 (15)C14—C13—H13119.8
C8—N2—N1118.79 (15)C9—C14—C13120.6 (2)
C8—N2—H2'123.7 (15)C9—C14—H14119.7
N1—N2—H2'117.5 (15)C13—C14—H14119.7
C21—N3—N4115.38 (15)F2—C15—C16118.13 (19)
C22—N4—N3119.63 (14)F2—C15—C20118.40 (18)
C22—N4—H4'126.0 (13)C16—C15—C20123.5 (2)
N3—N4—H4'113.9 (13)C17—C16—C15118.4 (2)
F1—C1—C2118.3 (2)C17—C16—H16120.8
F1—C1—C6117.84 (19)C15—C16—H16120.8
C2—C1—C6123.8 (2)C16—C17—C18120.3 (2)
C1—C2—C3118.7 (2)C16—C17—H17119.8
C1—C2—H2120.7C18—C17—H17119.8
C3—C2—H2120.7C17—C18—C19120.1 (2)
C2—C3—C4119.9 (2)C17—C18—H18119.9
C2—C3—H3120.1C19—C18—H18119.9
C4—C3—H3120.1C18—C19—C20121.1 (2)
C3—C4—C5120.4 (2)C18—C19—H19119.4
C3—C4—H4119.8C20—C19—H19119.4
C5—C4—H4119.8C15—C20—C19116.53 (18)
C4—C5—C6121.3 (2)C15—C20—C21120.25 (17)
C4—C5—H5119.4C19—C20—C21123.20 (18)
C6—C5—H5119.4N3—C21—C20121.54 (16)
C1—C6—C5115.95 (18)N3—C21—H21119.2
C1—C6—C7121.65 (18)C20—C21—H21119.2
C5—C6—C7122.37 (19)O2—C22—N4121.02 (16)
N1—C7—C6119.94 (17)O2—C22—C23121.70 (17)
N1—C7—H7120.0N4—C22—C23117.27 (15)
C6—C7—H7120.0C24—C23—C28118.78 (18)
O1—C8—N2121.89 (16)C24—C23—C22117.03 (17)
O1—C8—C9120.36 (18)C28—C23—C22124.17 (18)
N2—C8—C9117.73 (15)C23—C24—C25119.5 (2)
C10—C9—C14118.38 (19)C23—C24—H24120.3
C10—C9—C8117.23 (18)C25—C24—H24120.3
C14—C9—C8124.25 (19)C26—C25—C24120.9 (3)
C9—C10—C11120.9 (2)C26—C25—H25119.6
C9—C10—H10119.5C24—C25—H25119.6
C11—C10—H10119.5C27—C26—C25120.0 (2)
C12—C11—C10119.9 (3)C27—C26—H26120.0
C12—C11—H11120.0C25—C26—H26120.0
C10—C11—H11120.0C26—C27—C28120.0 (2)
C13—C12—C11119.7 (2)C26—C27—H27120.0
C13—C12—H12120.2C28—C27—H27120.0
C11—C12—H12120.2C23—C28—C27120.8 (2)
C12—C13—C14120.5 (2)C23—C28—H28119.6
C12—C13—H13119.8C27—C28—H28119.6
C7—N1—N2—C8177.11 (17)C12—C13—C14—C90.3 (4)
C21—N3—N4—C22178.37 (18)F2—C15—C16—C17−179.7 (2)
F1—C1—C2—C3−179.3 (2)C20—C15—C16—C170.8 (4)
C6—C1—C2—C3−0.3 (4)C15—C16—C17—C18−0.7 (4)
C1—C2—C3—C40.0 (4)C16—C17—C18—C190.3 (4)
C2—C3—C4—C50.2 (5)C17—C18—C19—C200.1 (3)
C3—C4—C5—C6−0.1 (4)F2—C15—C20—C19179.99 (19)
F1—C1—C6—C5179.36 (19)C16—C15—C20—C19−0.5 (3)
C2—C1—C6—C50.4 (3)F2—C15—C20—C211.8 (3)
F1—C1—C6—C7−2.7 (3)C16—C15—C20—C21−178.7 (2)
C2—C1—C6—C7178.3 (2)C18—C19—C20—C150.0 (3)
C4—C5—C6—C1−0.2 (3)C18—C19—C20—C21178.2 (2)
C4—C5—C6—C7−178.1 (2)N4—N3—C21—C20−178.78 (17)
N2—N1—C7—C6177.19 (16)C15—C20—C21—N3−178.67 (19)
C1—C6—C7—N1176.73 (19)C19—C20—C21—N33.3 (3)
C5—C6—C7—N1−5.5 (3)N3—N4—C22—O25.5 (3)
N1—N2—C8—O1−7.2 (3)N3—N4—C22—C23−174.97 (16)
N1—N2—C8—C9171.27 (15)O2—C22—C23—C244.0 (3)
O1—C8—C9—C10−9.0 (3)N4—C22—C23—C24−175.59 (18)
N2—C8—C9—C10172.51 (19)O2—C22—C23—C28−174.60 (19)
O1—C8—C9—C14166.5 (2)N4—C22—C23—C285.8 (3)
N2—C8—C9—C14−12.0 (3)C28—C23—C24—C25−0.1 (3)
C14—C9—C10—C11−0.5 (4)C22—C23—C24—C25−178.8 (2)
C8—C9—C10—C11175.3 (2)C23—C24—C25—C26−0.9 (4)
C9—C10—C11—C121.0 (4)C24—C25—C26—C271.0 (4)
C10—C11—C12—C13−0.9 (4)C25—C26—C27—C280.0 (4)
C11—C12—C13—C140.3 (4)C24—C23—C28—C271.1 (3)
C10—C9—C14—C13−0.1 (4)C22—C23—C28—C27179.6 (2)
C8—C9—C14—C13−175.6 (2)C26—C27—C28—C23−1.0 (4)
D—H···AD—HH···AD···AD—H···A
N2—H2′···O2i0.89 (1)2.09 (2)2.875 (2)147 (2)
N2—H2′···N3i0.89 (1)2.60 (2)3.339 (2)142 (2)
N4—H4′···O10.87 (1)2.03 (1)2.882 (2)171 (2)
C7—H7···O2i0.932.533.213 (2)131
C14—H14···O2i0.932.493.402 (3)166
C16—H16···O2ii0.932.553.450 (3)164
C21—H21···O10.932.443.250 (2)145
C28—H28···O10.932.403.312 (2)166
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A DA D—H⋯A
N2—H2′⋯O2i 0.89 (1)2.09 (2)2.875 (2)147 (2)
N2—H2′⋯N3i 0.89 (1)2.60 (2)3.339 (2)142 (2)
N4—H4′⋯O10.87 (1)2.03 (1)2.882 (2)171 (2)
C7—H7⋯O2i 0.932.533.213 (2)131
C14—H14⋯O2i 0.932.493.402 (3)166
C16—H16⋯O2ii 0.932.553.450 (3)164
C21—H21⋯O10.932.443.250 (2)145
C28—H28⋯O10.932.403.312 (2)166

Symmetry codes: (i) ; (ii) .

  3 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Structural study of ribonucleotide reductase inhibitor hydrazones. Synthesis and X-ray diffraction analysis of a copper(II)-benzoylpyridine-2-quinolinyl hydrazone complex.

Authors:  Gabriella Tamasi; Luisa Chiasserini; Luisa Savini; Alessandro Sega; Renzo Cini
Journal:  J Inorg Biochem       Date:  2005-06       Impact factor: 4.155

3.  N'-[(E)-(3-Fluoro-pyridin-2-yl)methyl-idene]benzohydrazide monohydrate.

Authors:  Yamuna Nair; M Sithambaresan; M R Prathapachandra Kurup
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-08-15
  3 in total
  1 in total

1.  N'-[(E)-1-(2-Fluoro-phen-yl)ethyl-idene]pyridine-4-carbohydrazide.

Authors:  P B Sreeja; M Sithambaresan; N Aiswarya; M R Prathapachandra Kurup
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-04-09
  1 in total

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