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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(E)-N′-(4-Fluoro­benzyl­­idene)-2-(3-methyl­phen­yl)acetohydrazide

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, 574 199, India
*Correspondence e-mail: jjasinski@keene.edu

(Received 9 December 2012; accepted 14 February 2013; online 23 February 2013)

In the title compound, C16H15FN2O, the dihedral angles between the benzene rings are74.7(8), 74.1 (1), 74.2 (7) and 74.3 (5)° in the four independent mol­ecules in the asymmetric unit. In the crystal, N—H—O hydrogen bonds involving the hydrazide and acetyl groups, which form R22(18) ring motifs, link the mol­ecules into dimers, which form columns along [010].

Related literature

For Schiff bases as ligands for complexation of metal ions, see: Aydogan et al. (2001[Aydogan, F., Ocal, N., Turgut, Z. & Yolacan, C. (2001). Bull. Korean Chem. Soc. 22, 476-480.]); their applications as dyes and pigments, see: Taggi et al. (2002[Taggi, A. E., Hafez, A. M., Wack, H., Young, B., Ferraris, D. & Lectka, T. (2002). J. Am. Chem. Soc. 124, 6626-6635.]) and crystallography and coordination chemistry, see: Kundu et al. (2005[Kundu, N., Chatterjee, P. B., Chaudhury, M. & Tiekink, E. R. T. (2005). Acta Cryst. E61, m1583-m1585.]); Xu et al. (1997[Xu, Z., Thompson, L. K. & Miller, D. O. (1997). Inorg. Chem. 36, 3985-3995.]). For related structures, see: Fun et al. (2011a[Fun, H.-K., Hemamalini, M., Sumangala, V., Prasad, D. J. & Poojary, B. (2011a). Acta Cryst. E67, o2847.],b[Fun, H.-K., Hemamalini, M., Sumangala, V., Nagaraja, G. K. & Poojary, B. (2011b). Acta Cryst. E67, o2835.], 2012[Fun, H.-K., Quah, C. K., Frank, P. V., Damodara, N. & Kalluraya, B. (2012). Acta Cryst. E68, o2192.]); He & Shi (2011[He, G.-F. & Shi, Z.-Q. (2011). Acta Cryst. E67, o48.]); Odabaşoğlu et al. (2007[Odabaşoğlu, M., Büyükgüngör, O., Sunil, K. & Narayana, B. (2007). Acta Cryst. E63, o4145-o4146.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C16H15FN2O

  • Mr = 270.30

  • Triclinic, [P \overline 1]

  • a = 11.8535 (7) Å

  • b = 12.3769 (9) Å

  • c = 20.8721 (11) Å

  • α = 98.549 (5)°

  • β = 103.074 (5)°

  • γ = 105.134 (6)°

  • V = 2808.2 (3) Å3

  • Z = 8

  • Cu Kα radiation

  • μ = 0.74 mm−1

  • T = 173 K

  • 0.22 × 0.16 × 0.08 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.780, Tmax = 1.000

  • 16410 measured reflections

  • 9250 independent reflections

  • 3807 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 0.191

  • S = 0.99

  • 9250 reflections

  • 725 parameters

  • H-atom parameters constrained

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1A—H1A⋯O1Bi 0.86 2.01 2.868 (3) 173
N1B—H1B⋯O1Ai 0.86 2.00 2.860 (3) 173
N1C—H1C⋯O1Dii 0.86 2.01 2.865 (3) 173
N1D—H1D⋯O1Ciii 0.86 2.00 2.857 (4) 173
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y-1, z-1; (iii) x+1, y+1, z+1.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]).

Supporting information


Comment top

Schiff bases are used as substrates in the preparation of number of industrial and biologically active compounds via ring closure, cycloaddition and replacement reactions. Schiff bases have also been employed as ligands for complexation of metal ions (Aydogan et al., 2001). On the industrial scale, they have wide range of applications such as dyes and pigments (Taggi et al., 2002). Compounds containing an azine functionality or a diimine linkage have been investigated in terms of their crystallography and coordination chemistry (Xu et al., 1997; Kundu et al., 2005). The crystal structures of some Schiff base hydrazines, viz., 4-fluorobenzaldehyde [(E)-4-fluorobenzylidene]hydrazone (Odabaşoğlu et al., 2007), N'-[(E)-1-(4-bromophenyl)ethylidene]-2-(2-methyl-4-nitro-1H-imidazol-1-yl) acetohydrazide, (Fun et al., 2012) N'-(4-Chlorobenzylidene)-2-[4-(methylsulfanyl)phenyl]acetohydrazide, N'-(4-fluorobenzylidene)-2-(4-fluorophenyl)acetohydrazide (Fun et al., 2011a,b) and 2-(1H-1,2,3-benzotriazol-1-yl)-N'-(2-chlorobenzylidene)acetohydrazide (He & Shi, 2011) have been reported. In view of the importance of Schiff base hydrazines, the crystal structure of title compound is reported.

In the title compound, four molecules (A, B, C, D) crystallize in the asymmetric unit (Fig. 1). The dihedral angle between the benzene rings are twisted by 74.7 (8)° (A), 74.1 (1)° (B), 74.2 (7)° (C) and 74.3 (5)° (D), respectively. Bond lengths are in normal ranges (Allen et al., 1987). In the crystal, N—H—O hydrogen bonds (Table 1) between hydrazide and aceto groups in nearby molecules forming an R 2,2(18) ring motif structure link the molecules into dimers which form columns along [010] (Fig. 2).

Related literature top

For Schiff bases as ligands for complexation of metal ions, see: Aydogan et al. (2001); their applications as dyes and pigments, see: Taggi et al. (2002) and crystallography and coordination chemistry, see: Kundu et al. (2005); Xu et al. (1997). For related structures, see: Fun et al. (2011a,b, 2012); He & Shi (2011); Odabaşoğlu et al. (2007). For standard bond lengths, see: Allen et al. (1987).

Experimental top

To a stirred solution of 2-m-tolylacetohydrazide (1g, 6.09 mmol) in ethanol (10 mL), 4-fluorobenzaldehyde (0.76 g, 6.09 mmol) was added and strirred at room temperature for 30 minutes (Fig. 3). Precipitated solid was filtered and dried. The single crystal was grown from toluene by the slow evaporation method and yield of the compound was 92%. (m.p.: 401–403 K).

Refinement top

All of the H atoms were placed in their calculated positions and then refined using the riding model with Atom—H lengths of 0.93Å (CH), 0.97Å (CH2), 0.96Å (CH3) or 0.86Å (NH). Isotropic displacement parameters for these atoms were set to 1.19-1.21 (CH, CH2), 1.49 (CH3) or 1.20 (NH) times Ueq of the parent atom.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with four molecules (A, B, C, D) in the asymmetric unit showing the atom labeling scheme and 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of the title compound viewed along the a axis. Dashed lines indicate N—H···O hydrogen bonds linkng the molecules into 1-D chains along [010] The remaining H atoms have been removed for clarity. [Symmetry code: (i) - x + 1, - y + 1, - z + 1; (ii) x - 1, y - 1, z - 1]
(E)-N'-(4-Fluorobenzylidene)-2-(3-methylphenyl)acetohydrazide top
Crystal data top
C16H15FN2OZ = 8
Mr = 270.30F(000) = 1136
Triclinic, P1Dx = 1.279 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54184 Å
a = 11.8535 (7) ÅCell parameters from 4137 reflections
b = 12.3769 (9) Åθ = 3.8–72.4°
c = 20.8721 (11) ŵ = 0.74 mm1
α = 98.549 (5)°T = 173 K
β = 103.074 (5)°Chunk, colorless
γ = 105.134 (6)°0.22 × 0.16 × 0.08 mm
V = 2808.2 (3) Å3
Data collection top
Agilent Xcalibur (Eos, Gemini)
diffractometer
9250 independent reflections
Radiation source: Enhance (Cu) X-ray Source3807 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
Detector resolution: 16.0416 pixels mm-1θmax = 63.7°, θmin = 3.8°
ω scansh = 1213
Absorption correction: multi-scan
(CrysAlis PRO and CrysAlis RED; Agilent, 2012)
k = 1413
Tmin = 0.780, Tmax = 1.000l = 1624
16410 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.191H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0836P)2]
where P = (Fo2 + 2Fc2)/3
9250 reflections(Δ/σ)max < 0.001
725 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C16H15FN2Oγ = 105.134 (6)°
Mr = 270.30V = 2808.2 (3) Å3
Triclinic, P1Z = 8
a = 11.8535 (7) ÅCu Kα radiation
b = 12.3769 (9) ŵ = 0.74 mm1
c = 20.8721 (11) ÅT = 173 K
α = 98.549 (5)°0.22 × 0.16 × 0.08 mm
β = 103.074 (5)°
Data collection top
Agilent Xcalibur (Eos, Gemini)
diffractometer
9250 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO and CrysAlis RED; Agilent, 2012)
3807 reflections with I > 2σ(I)
Tmin = 0.780, Tmax = 1.000Rint = 0.027
16410 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.191H-atom parameters constrained
S = 0.99Δρmax = 0.19 e Å3
9250 reflectionsΔρmin = 0.22 e Å3
725 parameters
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.

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*/Ueq
F1A0.1350 (2)0.4488 (2)0.58889 (13)0.0873 (9)
O1A0.6076 (2)0.3277 (2)0.57816 (11)0.0437 (7)
N1A0.4866 (2)0.1468 (2)0.55590 (13)0.0366 (7)
H1A0.45920.14900.51450.044*
N2A0.4417 (3)0.0477 (2)0.57697 (13)0.0383 (8)
C1A0.5722 (3)0.2402 (3)0.59807 (17)0.0366 (9)
C2A0.6254 (3)0.2316 (3)0.66978 (16)0.0424 (10)
H2AA0.57180.16780.68090.051*
H2AB0.63430.30140.70120.051*
C3A0.7487 (4)0.2136 (3)0.67480 (16)0.0380 (9)
C4A0.8535 (3)0.3072 (3)0.69544 (16)0.0421 (9)
H4A0.84770.37990.70970.051*
C5A0.9663 (4)0.2952 (4)0.69533 (19)0.0549 (12)
C6A0.9726 (4)0.1853 (4)0.67436 (19)0.0642 (14)
H6A1.04730.17460.67390.077*
C7A0.8674 (4)0.0909 (4)0.65398 (19)0.0579 (12)
H7A0.87280.01800.64000.069*
C8A0.7564 (4)0.1044 (3)0.65430 (16)0.0473 (11)
H8A0.68690.04110.64090.057*
C9A1.0773 (4)0.3989 (4)0.7144 (2)0.0813 (16)
H9AA1.09090.42290.67440.122*
H9AB1.14670.37980.73750.122*
H9AC1.06510.46000.74340.122*
C10A0.3539 (3)0.0306 (3)0.53391 (17)0.0393 (9)
H10A0.32450.01800.49140.047*
C11A0.2985 (4)0.1393 (3)0.54956 (18)0.0435 (10)
C12A0.1988 (4)0.2200 (4)0.5016 (2)0.0602 (12)
H12A0.16940.20340.46020.072*
C13A0.1427 (4)0.3244 (4)0.5145 (2)0.0693 (14)
H13A0.07630.37800.48250.083*
C14A0.1884 (4)0.3459 (4)0.5761 (2)0.0607 (12)
C15A0.2864 (4)0.2689 (4)0.6243 (2)0.0583 (12)
H15A0.31540.28650.66540.070*
C16A0.3415 (4)0.1650 (3)0.61114 (19)0.0476 (10)
H16A0.40770.11200.64370.057*
F1B0.1356 (2)0.0510 (2)0.58903 (13)0.0886 (9)
O1B0.6075 (2)0.8278 (2)0.57834 (11)0.0440 (7)
N1B0.4862 (2)0.6464 (2)0.55557 (13)0.0384 (8)
H1B0.45890.64860.51410.046*
N2B0.4414 (3)0.5482 (2)0.57698 (13)0.0368 (7)
C1B0.5719 (3)0.7395 (3)0.59798 (17)0.0358 (9)
C2B0.6264 (3)0.7321 (3)0.66962 (15)0.0420 (10)
H2BA0.63610.80260.70070.050*
H2BB0.57290.66910.68140.050*
C3B0.7486 (3)0.7131 (3)0.67475 (15)0.0368 (9)
C4B0.8532 (3)0.8068 (3)0.69576 (16)0.0407 (9)
H4B0.84760.87940.71060.049*
C5B0.9661 (4)0.7944 (4)0.69511 (19)0.0531 (12)
C6B0.9718 (4)0.6843 (4)0.6741 (2)0.0642 (13)
H6B1.04650.67370.67360.077*
C7B0.8696 (4)0.5918 (4)0.65430 (19)0.0608 (13)
H7B0.87530.51890.64040.073*
C8B0.7582 (4)0.6052 (3)0.65471 (16)0.0481 (11)
H8B0.68910.54140.64150.058*
C9B1.0768 (4)0.8985 (4)0.7144 (2)0.0846 (17)
H9BA1.05190.96640.71590.127*
H9BB1.12160.89420.68160.127*
H9BC1.12730.90110.75800.127*
C10B0.3550 (3)0.4701 (3)0.53307 (17)0.0399 (9)
H10B0.32800.48250.49020.048*
C11B0.2973 (4)0.3610 (3)0.54858 (18)0.0414 (9)
C12B0.1991 (4)0.2800 (4)0.5017 (2)0.0608 (12)
H12B0.16930.29630.46020.073*
C13B0.1434 (4)0.1756 (4)0.5140 (2)0.0683 (14)
H13B0.07740.12190.48160.082*
C14B0.1884 (4)0.1537 (4)0.5750 (2)0.0612 (13)
C15B0.2858 (4)0.2294 (4)0.6240 (2)0.0599 (12)
H15B0.31410.21140.66520.072*
C16B0.3411 (4)0.3340 (3)0.61045 (18)0.0466 (10)
H16B0.40780.38660.64280.056*
F1C0.3648 (3)0.3109 (2)0.08860 (14)0.0866 (9)
O1C0.1075 (2)0.2351 (2)0.07803 (11)0.0449 (7)
N1C0.0140 (2)0.1252 (2)0.05571 (13)0.0367 (7)
H1C0.04140.16170.01420.044*
N2C0.0584 (3)0.0385 (2)0.07720 (13)0.0368 (7)
C1C0.0715 (3)0.1546 (3)0.09808 (17)0.0382 (9)
C2C0.1263 (3)0.0834 (3)0.16952 (16)0.0419 (9)
H2CA0.07300.04070.18100.050*
H2CB0.13530.13320.20080.050*
C3C0.2487 (3)0.0017 (3)0.17474 (15)0.0375 (9)
C4C0.3534 (3)0.0315 (3)0.19560 (16)0.0421 (9)
H4C0.34760.09940.21050.051*
C5C0.4671 (4)0.0361 (4)0.19508 (19)0.0542 (11)
C6C0.4714 (4)0.1393 (4)0.17407 (19)0.0654 (14)
H6C0.54560.18780.17360.079*
C7C0.3665 (4)0.1700 (4)0.15395 (18)0.0582 (13)
H7C0.37120.23860.14000.070*
C8C0.2551 (4)0.0999 (3)0.15443 (16)0.0457 (10)
H8C0.18520.12120.14120.055*
C9C0.5790 (4)0.0030 (4)0.2150 (2)0.0817 (16)
H9CA0.58140.05680.17760.123*
H9CB0.57540.03890.25250.123*
H9CC0.65080.06220.22760.123*
C10C0.1451 (3)0.0259 (3)0.03379 (17)0.0417 (9)
H10C0.17350.07420.00890.050*
C11C0.2012 (4)0.0632 (3)0.04950 (18)0.0433 (10)
C12C0.1582 (4)0.1419 (3)0.11061 (19)0.0482 (10)
H12C0.09120.13940.14300.058*
C13C0.2144 (4)0.2244 (3)0.1238 (2)0.0589 (12)
H13C0.18610.27630.16530.071*
C14C0.3114 (5)0.2293 (4)0.0759 (3)0.0619 (13)
C15C0.3561 (4)0.1544 (4)0.0149 (2)0.0676 (14)
H15C0.42210.15910.01730.081*
C16C0.3010 (4)0.0709 (4)0.00196 (19)0.0606 (12)
H16C0.33110.01870.03940.073*
F1D1.3651 (3)0.1892 (2)0.91119 (14)0.0887 (9)
O1D0.8924 (2)0.7349 (2)0.92168 (11)0.0439 (7)
N1D1.0131 (3)0.6259 (2)0.94424 (13)0.0386 (8)
H1D1.04000.66250.98570.046*
N2D1.0586 (3)0.5392 (2)0.92337 (13)0.0381 (8)
C1D0.9281 (3)0.6553 (3)0.90193 (16)0.0352 (8)
C2D0.8742 (3)0.5849 (3)0.83039 (15)0.0416 (10)
H2DA0.92770.54260.81880.050*
H2DB0.86480.63500.79930.050*
C3D0.7511 (3)0.5021 (3)0.82527 (15)0.0372 (9)
C4D0.6466 (3)0.5325 (3)0.80431 (16)0.0413 (9)
H4D0.65220.60060.78960.050*
C5D0.5344 (4)0.4645 (4)0.80461 (19)0.0525 (11)
C6D0.5272 (4)0.3623 (4)0.8256 (2)0.0642 (13)
H6D0.45210.31510.82580.077*
C7D0.6295 (4)0.3298 (3)0.84599 (19)0.0604 (13)
H7D0.62330.26120.86020.072*
C8D0.7410 (4)0.3984 (3)0.84551 (16)0.0485 (11)
H8D0.80990.37550.85870.058*
C9D0.4222 (4)0.5016 (4)0.7854 (2)0.0811 (16)
H9DA0.40220.52970.82550.122*
H9DB0.35550.43740.75750.122*
H9DC0.43730.56150.76110.122*
C10D1.1461 (3)0.5258 (3)0.96689 (16)0.0397 (9)
H10D1.17440.57361.00970.048*
C11D1.2027 (3)0.4376 (3)0.95104 (18)0.0419 (9)
C12D1.1598 (4)0.3588 (3)0.88932 (19)0.0490 (10)
H12D1.09360.36230.85670.059*
C13D1.2147 (4)0.2754 (3)0.8760 (2)0.0609 (12)
H13D1.18640.22260.83490.073*
C14D1.3122 (4)0.2728 (4)0.9252 (2)0.0602 (13)
C15D1.3568 (4)0.3485 (4)0.9863 (2)0.0713 (14)
H15D1.42360.34521.01850.086*
C16D1.3001 (4)0.4297 (4)0.99869 (19)0.0581 (12)
H16D1.32820.48081.04040.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F1A0.107 (2)0.0493 (17)0.119 (2)0.0109 (16)0.0676 (19)0.0286 (16)
O1A0.0440 (16)0.0344 (15)0.0420 (14)0.0024 (12)0.0028 (12)0.0073 (12)
N1A0.0375 (19)0.0345 (18)0.0312 (16)0.0073 (14)0.0019 (14)0.0064 (14)
N2A0.0387 (19)0.0354 (19)0.0388 (17)0.0079 (15)0.0107 (15)0.0078 (15)
C1A0.034 (2)0.038 (2)0.034 (2)0.0094 (17)0.0054 (17)0.0028 (17)
C2A0.044 (2)0.044 (2)0.035 (2)0.0111 (19)0.0073 (19)0.0077 (17)
C3A0.047 (2)0.037 (2)0.0264 (19)0.0099 (18)0.0050 (18)0.0084 (17)
C4A0.046 (3)0.042 (2)0.035 (2)0.0125 (19)0.0045 (19)0.0093 (17)
C5A0.045 (3)0.080 (4)0.045 (2)0.022 (3)0.011 (2)0.026 (2)
C6A0.062 (3)0.108 (4)0.051 (3)0.055 (3)0.026 (2)0.037 (3)
C7A0.081 (4)0.060 (3)0.046 (2)0.040 (3)0.018 (3)0.018 (2)
C8A0.063 (3)0.045 (3)0.031 (2)0.017 (2)0.007 (2)0.0087 (18)
C9A0.045 (3)0.116 (5)0.079 (3)0.009 (3)0.010 (3)0.045 (3)
C10A0.037 (2)0.042 (2)0.035 (2)0.0091 (18)0.0066 (17)0.0053 (17)
C11A0.049 (3)0.041 (2)0.042 (2)0.0127 (19)0.020 (2)0.0060 (19)
C12A0.064 (3)0.052 (3)0.046 (2)0.007 (2)0.012 (2)0.004 (2)
C13A0.077 (4)0.046 (3)0.071 (3)0.004 (2)0.027 (3)0.001 (3)
C14A0.073 (4)0.038 (3)0.084 (3)0.014 (2)0.048 (3)0.019 (2)
C15A0.068 (3)0.055 (3)0.068 (3)0.027 (2)0.032 (3)0.026 (2)
C16A0.050 (3)0.045 (3)0.051 (2)0.014 (2)0.018 (2)0.016 (2)
F1B0.112 (2)0.0460 (16)0.124 (2)0.0121 (16)0.072 (2)0.0309 (16)
O1B0.0454 (16)0.0391 (16)0.0371 (14)0.0038 (12)0.0020 (12)0.0079 (12)
N1B0.0401 (19)0.0368 (19)0.0320 (16)0.0053 (15)0.0055 (15)0.0070 (14)
N2B0.043 (2)0.0325 (18)0.0324 (16)0.0103 (15)0.0078 (15)0.0068 (14)
C1B0.038 (2)0.033 (2)0.0335 (19)0.0088 (17)0.0079 (17)0.0037 (16)
C2B0.045 (2)0.043 (2)0.0285 (19)0.0038 (19)0.0066 (18)0.0022 (16)
C3B0.042 (2)0.044 (2)0.0217 (18)0.0132 (19)0.0041 (17)0.0077 (16)
C4B0.042 (2)0.046 (2)0.0298 (19)0.0107 (19)0.0042 (18)0.0088 (17)
C5B0.042 (3)0.076 (3)0.041 (2)0.015 (2)0.006 (2)0.025 (2)
C6B0.059 (3)0.098 (4)0.060 (3)0.045 (3)0.027 (3)0.036 (3)
C7B0.090 (4)0.067 (3)0.049 (3)0.048 (3)0.030 (3)0.023 (2)
C8B0.065 (3)0.045 (3)0.034 (2)0.017 (2)0.011 (2)0.0106 (19)
C9B0.042 (3)0.110 (4)0.089 (4)0.001 (3)0.003 (3)0.048 (3)
C10B0.048 (3)0.036 (2)0.033 (2)0.0095 (19)0.0121 (18)0.0040 (17)
C11B0.046 (2)0.036 (2)0.041 (2)0.0086 (18)0.0158 (19)0.0031 (18)
C12B0.072 (3)0.047 (3)0.051 (3)0.001 (2)0.020 (2)0.007 (2)
C13B0.073 (4)0.049 (3)0.064 (3)0.012 (2)0.026 (3)0.002 (2)
C14B0.074 (4)0.037 (3)0.083 (3)0.008 (2)0.051 (3)0.013 (2)
C15B0.070 (3)0.059 (3)0.071 (3)0.029 (3)0.039 (3)0.032 (3)
C16B0.050 (3)0.045 (3)0.049 (2)0.018 (2)0.019 (2)0.0085 (19)
F1C0.108 (2)0.0767 (19)0.122 (2)0.0641 (18)0.0694 (19)0.0417 (17)
O1C0.0459 (17)0.0461 (16)0.0402 (14)0.0205 (13)0.0012 (13)0.0066 (12)
N1C0.0380 (19)0.0382 (18)0.0299 (16)0.0136 (15)0.0020 (14)0.0037 (13)
N2C0.0381 (19)0.0402 (19)0.0354 (16)0.0165 (15)0.0106 (15)0.0103 (14)
C1C0.039 (2)0.038 (2)0.037 (2)0.0118 (18)0.0080 (18)0.0122 (17)
C2C0.040 (2)0.049 (2)0.033 (2)0.0143 (19)0.0048 (18)0.0060 (18)
C3C0.047 (3)0.040 (2)0.0247 (18)0.0169 (19)0.0067 (17)0.0036 (16)
C4C0.045 (3)0.042 (2)0.034 (2)0.0126 (19)0.0051 (18)0.0039 (17)
C5C0.042 (3)0.066 (3)0.043 (2)0.008 (2)0.011 (2)0.006 (2)
C6C0.070 (3)0.057 (3)0.050 (3)0.015 (3)0.028 (2)0.004 (2)
C7C0.082 (4)0.048 (3)0.041 (2)0.017 (3)0.017 (2)0.006 (2)
C8C0.058 (3)0.043 (3)0.032 (2)0.016 (2)0.008 (2)0.0031 (18)
C9C0.040 (3)0.103 (4)0.082 (3)0.020 (3)0.005 (3)0.019 (3)
C10C0.047 (3)0.047 (2)0.035 (2)0.019 (2)0.0127 (19)0.0087 (18)
C11C0.050 (3)0.051 (3)0.039 (2)0.022 (2)0.019 (2)0.0179 (19)
C12C0.055 (3)0.044 (3)0.052 (2)0.018 (2)0.024 (2)0.0136 (19)
C13C0.071 (3)0.049 (3)0.067 (3)0.021 (2)0.036 (3)0.010 (2)
C14C0.076 (4)0.057 (3)0.085 (3)0.041 (3)0.052 (3)0.031 (3)
C15C0.069 (3)0.090 (4)0.076 (3)0.056 (3)0.032 (3)0.042 (3)
C16C0.070 (3)0.074 (3)0.045 (2)0.038 (3)0.011 (2)0.014 (2)
F1D0.110 (2)0.083 (2)0.121 (2)0.0664 (18)0.0681 (19)0.0434 (17)
O1D0.0444 (17)0.0448 (16)0.0394 (14)0.0202 (13)0.0018 (12)0.0039 (12)
N1D0.041 (2)0.0401 (19)0.0324 (16)0.0161 (15)0.0046 (15)0.0039 (14)
N2D0.041 (2)0.0378 (19)0.0346 (16)0.0127 (15)0.0084 (15)0.0068 (14)
C1D0.031 (2)0.041 (2)0.033 (2)0.0126 (17)0.0052 (17)0.0082 (16)
C2D0.043 (3)0.051 (3)0.0312 (19)0.017 (2)0.0074 (18)0.0092 (18)
C3D0.041 (2)0.042 (2)0.0225 (17)0.0107 (18)0.0037 (17)0.0008 (16)
C4D0.044 (2)0.045 (2)0.0310 (19)0.0137 (19)0.0050 (18)0.0040 (17)
C5D0.042 (3)0.058 (3)0.043 (2)0.007 (2)0.006 (2)0.010 (2)
C6D0.055 (3)0.061 (3)0.058 (3)0.006 (2)0.023 (2)0.010 (2)
C7D0.086 (4)0.036 (3)0.051 (3)0.000 (2)0.027 (3)0.006 (2)
C8D0.073 (3)0.045 (3)0.030 (2)0.027 (2)0.010 (2)0.0053 (18)
C9D0.045 (3)0.101 (4)0.078 (3)0.018 (3)0.007 (3)0.015 (3)
C10D0.041 (2)0.044 (2)0.033 (2)0.0152 (18)0.0046 (17)0.0099 (17)
C11D0.044 (3)0.044 (2)0.046 (2)0.0172 (19)0.018 (2)0.0174 (19)
C12D0.051 (3)0.050 (3)0.052 (2)0.019 (2)0.017 (2)0.017 (2)
C13D0.072 (3)0.050 (3)0.070 (3)0.021 (2)0.036 (3)0.013 (2)
C14D0.067 (3)0.064 (3)0.085 (3)0.043 (3)0.046 (3)0.041 (3)
C15D0.076 (4)0.100 (4)0.057 (3)0.053 (3)0.018 (3)0.027 (3)
C16D0.063 (3)0.078 (3)0.049 (2)0.048 (3)0.015 (2)0.017 (2)
Geometric parameters (Å, º) top
F1A—C14A1.361 (4)F1C—C14C1.350 (4)
O1A—C1A1.223 (4)O1C—C1C1.236 (4)
N1A—C1A1.350 (4)N1C—C1C1.351 (4)
N1A—N2A1.380 (3)N1C—N2C1.374 (3)
N1A—H1A0.8600N1C—H1C0.8600
N2A—C10A1.273 (4)N2C—C10C1.267 (4)
C1A—C2A1.518 (4)C1C—C2C1.515 (4)
C2A—C3A1.519 (4)C2C—C3C1.507 (5)
C2A—H2AA0.9700C2C—H2CA0.9700
C2A—H2AB0.9700C2C—H2CB0.9700
C3A—C8A1.388 (5)C3C—C8C1.374 (4)
C3A—C4A1.389 (5)C3C—C4C1.382 (4)
C4A—C5A1.383 (5)C4C—C5C1.392 (5)
C4A—H4A0.9300C4C—H4C0.9300
C5A—C6A1.393 (6)C5C—C6C1.403 (5)
C5A—C9A1.505 (5)C5C—C9C1.520 (5)
C6A—C7A1.397 (6)C6C—C7C1.387 (5)
C6A—H6A0.9300C6C—H6C0.9300
C7A—C8A1.370 (5)C7C—C8C1.381 (5)
C7A—H7A0.9300C7C—H7C0.9300
C8A—H8A0.9300C8C—H8C0.9300
C9A—H9AA0.9600C9C—H9CA0.9600
C9A—H9AB0.9600C9C—H9CB0.9600
C9A—H9AC0.9600C9C—H9CC0.9600
C10A—C11A1.454 (5)C10C—C11C1.463 (5)
C10A—H10A0.9300C10C—H10C0.9300
C11A—C16A1.386 (4)C11C—C12C1.383 (5)
C11A—C12A1.395 (5)C11C—C16C1.396 (5)
C12A—C13A1.386 (5)C12C—C13C1.384 (5)
C12A—H12A0.9300C12C—H12C0.9300
C13A—C14A1.370 (5)C13C—C14C1.364 (5)
C13A—H13A0.9300C13C—H13C0.9300
C14A—C15A1.370 (6)C14C—C15C1.360 (6)
C15A—C16A1.380 (5)C15C—C16C1.385 (5)
C15A—H15A0.9300C15C—H15C0.9300
C16A—H16A0.9300C16C—H16C0.9300
F1B—C14B1.368 (4)F1D—C14D1.371 (4)
O1B—C1B1.229 (4)O1D—C1D1.222 (4)
N1B—C1B1.349 (4)N1D—C1D1.346 (4)
N1B—N2B1.376 (3)N1D—N2D1.379 (3)
N1B—H1B0.8600N1D—H1D0.8600
N2B—C10B1.272 (4)N2D—C10D1.279 (4)
C1B—C2B1.515 (4)C1D—C2D1.513 (4)
C2B—C3B1.509 (4)C2D—C3D1.519 (5)
C2B—H2BA0.9700C2D—H2DA0.9700
C2B—H2BB0.9700C2D—H2DB0.9700
C3B—C8B1.381 (5)C3D—C4D1.383 (4)
C3B—C4B1.388 (5)C3D—C8D1.395 (4)
C4B—C5B1.389 (5)C4D—C5D1.378 (5)
C4B—H4B0.9300C4D—H4D0.9300
C5B—C6B1.392 (6)C5D—C6D1.387 (5)
C5B—C9B1.505 (5)C5D—C9D1.508 (5)
C6B—C7B1.363 (6)C6D—C7D1.373 (5)
C6B—H6B0.9300C6D—H6D0.9300
C7B—C8B1.375 (5)C7D—C8D1.375 (5)
C7B—H7B0.9300C7D—H7D0.9300
C8B—H8B0.9300C8D—H8D0.9300
C9B—H9BA0.9600C9D—H9DA0.9600
C9B—H9BB0.9600C9D—H9DB0.9600
C9B—H9BC0.9600C9D—H9DC0.9600
C10B—C11B1.463 (4)C10D—C11D1.459 (4)
C10B—H10B0.9300C10D—H10D0.9300
C11B—C12B1.380 (5)C11D—C16D1.378 (5)
C11B—C16B1.402 (4)C11D—C12D1.393 (5)
C12B—C13B1.379 (5)C12D—C13D1.383 (5)
C12B—H12B0.9300C12D—H12D0.9300
C13B—C14B1.360 (5)C13D—C14D1.371 (5)
C13B—H13B0.9300C13D—H13D0.9300
C14B—C15B1.369 (6)C14D—C15D1.366 (6)
C15B—C16B1.391 (5)C15D—C16D1.371 (5)
C15B—H15B0.9300C15D—H15D0.9300
C16B—H16B0.9300C16D—H16D0.9300
C1A—N1A—N2A122.3 (3)C1C—N1C—N2C121.7 (3)
C1A—N1A—H1A118.9C1C—N1C—H1C119.1
N2A—N1A—H1A118.9N2C—N1C—H1C119.1
C10A—N2A—N1A116.1 (3)C10C—N2C—N1C115.2 (3)
O1A—C1A—N1A120.6 (3)O1C—C1C—N1C120.5 (3)
O1A—C1A—C2A121.5 (3)O1C—C1C—C2C120.9 (3)
N1A—C1A—C2A117.9 (3)N1C—C1C—C2C118.5 (3)
C1A—C2A—C3A108.2 (3)C3C—C2C—C1C109.1 (3)
C1A—C2A—H2AA110.1C3C—C2C—H2CA109.9
C3A—C2A—H2AA110.1C1C—C2C—H2CA109.9
C1A—C2A—H2AB110.1C3C—C2C—H2CB109.9
C3A—C2A—H2AB110.1C1C—C2C—H2CB109.9
H2AA—C2A—H2AB108.4H2CA—C2C—H2CB108.3
C8A—C3A—C4A119.7 (4)C8C—C3C—C4C119.9 (4)
C8A—C3A—C2A120.1 (4)C8C—C3C—C2C119.5 (3)
C4A—C3A—C2A120.1 (3)C4C—C3C—C2C120.4 (3)
C5A—C4A—C3A121.8 (4)C3C—C4C—C5C122.5 (4)
C5A—C4A—H4A119.1C3C—C4C—H4C118.8
C3A—C4A—H4A119.1C5C—C4C—H4C118.8
C4A—C5A—C6A118.0 (4)C4C—C5C—C6C116.5 (4)
C4A—C5A—C9A120.6 (4)C4C—C5C—C9C120.8 (4)
C6A—C5A—C9A121.4 (4)C6C—C5C—C9C122.7 (4)
C5A—C6A—C7A120.4 (4)C7C—C6C—C5C121.0 (4)
C5A—C6A—H6A119.8C7C—C6C—H6C119.5
C7A—C6A—H6A119.8C5C—C6C—H6C119.5
C8A—C7A—C6A120.9 (4)C8C—C7C—C6C120.8 (4)
C8A—C7A—H7A119.6C8C—C7C—H7C119.6
C6A—C7A—H7A119.6C6C—C7C—H7C119.6
C7A—C8A—C3A119.4 (4)C3C—C8C—C7C119.3 (4)
C7A—C8A—H8A120.3C3C—C8C—H8C120.4
C3A—C8A—H8A120.3C7C—C8C—H8C120.4
C5A—C9A—H9AA109.5C5C—C9C—H9CA109.5
C5A—C9A—H9AB109.5C5C—C9C—H9CB109.5
H9AA—C9A—H9AB109.5H9CA—C9C—H9CB109.5
C5A—C9A—H9AC109.5C5C—C9C—H9CC109.5
H9AA—C9A—H9AC109.5H9CA—C9C—H9CC109.5
H9AB—C9A—H9AC109.5H9CB—C9C—H9CC109.5
N2A—C10A—C11A121.7 (3)N2C—C10C—C11C121.3 (3)
N2A—C10A—H10A119.1N2C—C10C—H10C119.4
C11A—C10A—H10A119.1C11C—C10C—H10C119.4
C16A—C11A—C12A118.9 (4)C12C—C11C—C16C118.0 (4)
C16A—C11A—C10A121.8 (4)C12C—C11C—C10C122.1 (3)
C12A—C11A—C10A119.3 (3)C16C—C11C—C10C120.0 (4)
C13A—C12A—C11A121.2 (4)C11C—C12C—C13C120.4 (4)
C13A—C12A—H12A119.4C11C—C12C—H12C119.8
C11A—C12A—H12A119.4C13C—C12C—H12C119.8
C14A—C13A—C12A117.8 (4)C14C—C13C—C12C119.8 (4)
C14A—C13A—H13A121.1C14C—C13C—H13C120.1
C12A—C13A—H13A121.1C12C—C13C—H13C120.1
F1A—C14A—C15A119.2 (4)F1C—C14C—C15C118.5 (4)
F1A—C14A—C13A118.2 (4)F1C—C14C—C13C119.7 (5)
C15A—C14A—C13A122.6 (4)C15C—C14C—C13C121.9 (4)
C14A—C15A—C16A119.3 (4)C14C—C15C—C16C118.3 (4)
C14A—C15A—H15A120.3C14C—C15C—H15C120.8
C16A—C15A—H15A120.3C16C—C15C—H15C120.8
C15A—C16A—C11A120.2 (4)C15C—C16C—C11C121.6 (4)
C15A—C16A—H16A119.9C15C—C16C—H16C119.2
C11A—C16A—H16A119.9C11C—C16C—H16C119.2
C1B—N1B—N2B121.7 (3)C1D—N1D—N2D122.3 (3)
C1B—N1B—H1B119.1C1D—N1D—H1D118.8
N2B—N1B—H1B119.1N2D—N1D—H1D118.8
C10B—N2B—N1B115.1 (3)C10D—N2D—N1D116.3 (3)
O1B—C1B—N1B120.6 (3)O1D—C1D—N1D120.5 (3)
O1B—C1B—C2B120.5 (3)O1D—C1D—C2D120.8 (3)
N1B—C1B—C2B118.9 (3)N1D—C1D—C2D118.6 (3)
C3B—C2B—C1B108.9 (3)C1D—C2D—C3D108.6 (3)
C3B—C2B—H2BA109.9C1D—C2D—H2DA110.0
C1B—C2B—H2BA109.9C3D—C2D—H2DA110.0
C3B—C2B—H2BB109.9C1D—C2D—H2DB110.0
C1B—C2B—H2BB109.9C3D—C2D—H2DB110.0
H2BA—C2B—H2BB108.3H2DA—C2D—H2DB108.4
C8B—C3B—C4B119.0 (4)C4D—C3D—C8D118.6 (4)
C8B—C3B—C2B121.4 (4)C4D—C3D—C2D119.8 (3)
C4B—C3B—C2B119.5 (3)C8D—C3D—C2D121.4 (3)
C3B—C4B—C5B121.4 (4)C5D—C4D—C3D121.7 (4)
C3B—C4B—H4B119.3C5D—C4D—H4D119.2
C5B—C4B—H4B119.3C3D—C4D—H4D119.2
C4B—C5B—C6B117.9 (4)C4D—C5D—C6D118.5 (4)
C4B—C5B—C9B120.1 (4)C4D—C5D—C9D121.2 (4)
C6B—C5B—C9B122.0 (4)C6D—C5D—C9D120.3 (4)
C7B—C6B—C5B121.0 (4)C7D—C6D—C5D120.9 (4)
C7B—C6B—H6B119.5C7D—C6D—H6D119.6
C5B—C6B—H6B119.5C5D—C6D—H6D119.6
C6B—C7B—C8B120.6 (4)C6D—C7D—C8D120.1 (4)
C6B—C7B—H7B119.7C6D—C7D—H7D119.9
C8B—C7B—H7B119.7C8D—C7D—H7D119.9
C7B—C8B—C3B120.1 (4)C7D—C8D—C3D120.2 (4)
C7B—C8B—H8B119.9C7D—C8D—H8D119.9
C3B—C8B—H8B119.9C3D—C8D—H8D119.9
C5B—C9B—H9BA109.5C5D—C9D—H9DA109.5
C5B—C9B—H9BB109.5C5D—C9D—H9DB109.5
H9BA—C9B—H9BB109.5H9DA—C9D—H9DB109.5
C5B—C9B—H9BC109.5C5D—C9D—H9DC109.5
H9BA—C9B—H9BC109.5H9DA—C9D—H9DC109.5
H9BB—C9B—H9BC109.5H9DB—C9D—H9DC109.5
N2B—C10B—C11B121.4 (3)N2D—C10D—C11D121.7 (3)
N2B—C10B—H10B119.3N2D—C10D—H10D119.2
C11B—C10B—H10B119.3C11D—C10D—H10D119.2
C12B—C11B—C16B117.7 (4)C16D—C11D—C12D118.5 (4)
C12B—C11B—C10B120.7 (3)C16D—C11D—C10D119.5 (4)
C16B—C11B—C10B121.6 (4)C12D—C11D—C10D122.0 (3)
C13B—C12B—C11B122.4 (4)C13D—C12D—C11D120.6 (4)
C13B—C12B—H12B118.8C13D—C12D—H12D119.7
C11B—C12B—H12B118.8C11D—C12D—H12D119.7
C14B—C13B—C12B117.7 (4)C14D—C13D—C12D118.2 (4)
C14B—C13B—H13B121.2C14D—C13D—H13D120.9
C12B—C13B—H13B121.2C12D—C13D—H13D120.9
C13B—C14B—F1B119.4 (4)C15D—C14D—F1D119.8 (4)
C13B—C14B—C15B123.4 (4)C15D—C14D—C13D122.9 (4)
F1B—C14B—C15B117.2 (4)F1D—C14D—C13D117.3 (4)
C14B—C15B—C16B118.0 (4)C14D—C15D—C16D117.9 (4)
C14B—C15B—H15B121.0C14D—C15D—H15D121.0
C16B—C15B—H15B121.0C16D—C15D—H15D121.0
C15B—C16B—C11B120.8 (4)C15D—C16D—C11D121.9 (4)
C15B—C16B—H16B119.6C15D—C16D—H16D119.1
C11B—C16B—H16B119.6C11D—C16D—H16D119.1
C1A—N1A—N2A—C10A174.1 (3)C1C—N1C—N2C—C10C174.6 (3)
N2A—N1A—C1A—O1A178.0 (3)N2C—N1C—C1C—O1C177.9 (3)
N2A—N1A—C1A—C2A4.0 (5)N2C—N1C—C1C—C2C4.9 (5)
O1A—C1A—C2A—C3A76.9 (4)O1C—C1C—C2C—C3C76.7 (4)
N1A—C1A—C2A—C3A101.1 (4)N1C—C1C—C2C—C3C100.6 (4)
C1A—C2A—C3A—C8A82.7 (4)C1C—C2C—C3C—C8C82.4 (4)
C1A—C2A—C3A—C4A92.8 (4)C1C—C2C—C3C—C4C93.4 (4)
C8A—C3A—C4A—C5A0.9 (5)C8C—C3C—C4C—C5C2.0 (6)
C2A—C3A—C4A—C5A174.6 (3)C2C—C3C—C4C—C5C173.7 (3)
C3A—C4A—C5A—C6A0.6 (6)C3C—C4C—C5C—C6C1.9 (6)
C3A—C4A—C5A—C9A176.7 (3)C3C—C4C—C5C—C9C176.8 (3)
C4A—C5A—C6A—C7A0.2 (6)C4C—C5C—C6C—C7C1.1 (6)
C9A—C5A—C6A—C7A177.1 (4)C9C—C5C—C6C—C7C177.7 (3)
C5A—C6A—C7A—C8A0.1 (6)C5C—C6C—C7C—C8C0.3 (6)
C6A—C7A—C8A—C3A0.4 (6)C4C—C3C—C8C—C7C1.2 (5)
C4A—C3A—C8A—C7A0.8 (5)C2C—C3C—C8C—C7C174.6 (3)
C2A—C3A—C8A—C7A174.7 (3)C6C—C7C—C8C—C3C0.4 (6)
N1A—N2A—C10A—C11A179.8 (3)N1C—N2C—C10C—C11C179.9 (3)
N2A—C10A—C11A—C16A2.7 (6)N2C—C10C—C11C—C12C3.9 (6)
N2A—C10A—C11A—C12A177.0 (4)N2C—C10C—C11C—C16C176.4 (3)
C16A—C11A—C12A—C13A0.0 (7)C16C—C11C—C12C—C13C0.8 (6)
C10A—C11A—C12A—C13A179.6 (4)C10C—C11C—C12C—C13C179.5 (3)
C11A—C12A—C13A—C14A0.0 (7)C11C—C12C—C13C—C14C1.1 (6)
C12A—C13A—C14A—F1A179.1 (4)C12C—C13C—C14C—F1C179.1 (3)
C12A—C13A—C14A—C15A0.3 (7)C12C—C13C—C14C—C15C0.6 (7)
F1A—C14A—C15A—C16A179.3 (3)F1C—C14C—C15C—C16C179.9 (4)
C13A—C14A—C15A—C16A0.5 (7)C13C—C14C—C15C—C16C0.2 (7)
C14A—C15A—C16A—C11A0.4 (6)C14C—C15C—C16C—C11C0.5 (7)
C12A—C11A—C16A—C15A0.2 (6)C12C—C11C—C16C—C15C0.0 (6)
C10A—C11A—C16A—C15A179.8 (4)C10C—C11C—C16C—C15C179.7 (4)
C1B—N1B—N2B—C10B175.3 (3)C1D—N1D—N2D—C10D174.4 (3)
N2B—N1B—C1B—O1B177.4 (3)N2D—N1D—C1D—O1D177.8 (3)
N2B—N1B—C1B—C2B4.6 (5)N2D—N1D—C1D—C2D4.6 (5)
O1B—C1B—C2B—C3B77.7 (4)O1D—C1D—C2D—C3D77.3 (4)
N1B—C1B—C2B—C3B100.3 (4)N1D—C1D—C2D—C3D100.3 (4)
C1B—C2B—C3B—C8B81.8 (4)C1D—C2D—C3D—C4D93.7 (4)
C1B—C2B—C3B—C4B93.8 (4)C1D—C2D—C3D—C8D82.0 (4)
C8B—C3B—C4B—C5B1.9 (5)C8D—C3D—C4D—C5D1.7 (5)
C2B—C3B—C4B—C5B173.8 (3)C2D—C3D—C4D—C5D174.2 (3)
C3B—C4B—C5B—C6B1.5 (5)C3D—C4D—C5D—C6D1.1 (6)
C3B—C4B—C5B—C9B176.5 (3)C3D—C4D—C5D—C9D176.5 (3)
C4B—C5B—C6B—C7B0.6 (6)C4D—C5D—C6D—C7D0.4 (6)
C9B—C5B—C6B—C7B177.3 (4)C9D—C5D—C6D—C7D177.1 (4)
C5B—C6B—C7B—C8B0.1 (6)C5D—C6D—C7D—C8D0.4 (6)
C6B—C7B—C8B—C3B0.6 (6)C6D—C7D—C8D—C3D1.0 (6)
C4B—C3B—C8B—C7B1.4 (5)C4D—C3D—C8D—C7D1.6 (5)
C2B—C3B—C8B—C7B174.2 (3)C2D—C3D—C8D—C7D174.2 (3)
N1B—N2B—C10B—C11B179.5 (3)N1D—N2D—C10D—C11D179.6 (3)
N2B—C10B—C11B—C12B176.1 (4)N2D—C10D—C11D—C16D177.3 (3)
N2B—C10B—C11B—C16B5.4 (6)N2D—C10D—C11D—C12D4.1 (6)
C16B—C11B—C12B—C13B0.5 (7)C16D—C11D—C12D—C13D0.7 (6)
C10B—C11B—C12B—C13B179.0 (4)C10D—C11D—C12D—C13D179.4 (3)
C11B—C12B—C13B—C14B0.1 (7)C11D—C12D—C13D—C14D0.0 (6)
C12B—C13B—C14B—F1B180.0 (4)C12D—C13D—C14D—C15D0.1 (7)
C12B—C13B—C14B—C15B0.5 (7)C12D—C13D—C14D—F1D179.7 (3)
C13B—C14B—C15B—C16B0.1 (7)F1D—C14D—C15D—C16D179.0 (4)
F1B—C14B—C15B—C16B179.6 (3)C13D—C14D—C15D—C16D0.6 (7)
C14B—C15B—C16B—C11B0.6 (6)C14D—C15D—C16D—C11D1.5 (7)
C12B—C11B—C16B—C15B0.8 (6)C12D—C11D—C16D—C15D1.5 (7)
C10B—C11B—C16B—C15B179.3 (4)C10D—C11D—C16D—C15D179.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O1Bi0.862.012.868 (3)173
N1B—H1B···O1Ai0.862.002.860 (3)173
N1C—H1C···O1Dii0.862.012.865 (3)173
N1D—H1D···O1Ciii0.862.002.857 (4)173
Symmetry codes: (i) x+1, y+1, z+1; (ii) x1, y1, z1; (iii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC16H15FN2O
Mr270.30
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)11.8535 (7), 12.3769 (9), 20.8721 (11)
α, β, γ (°)98.549 (5), 103.074 (5), 105.134 (6)
V3)2808.2 (3)
Z8
Radiation typeCu Kα
µ (mm1)0.74
Crystal size (mm)0.22 × 0.16 × 0.08
Data collection
DiffractometerAgilent Xcalibur (Eos, Gemini)
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO and CrysAlis RED; Agilent, 2012)
Tmin, Tmax0.780, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
16410, 9250, 3807
Rint0.027
(sin θ/λ)max1)0.581
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.191, 0.99
No. of reflections9250
No. of parameters725
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.22

Computer programs: CrysAlis PRO (Agilent, 2012), CrysAlis RED (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O1Bi0.862.012.868 (3)173.2
N1B—H1B···O1Ai0.862.002.860 (3)172.8
N1C—H1C···O1Dii0.862.012.865 (3)172.8
N1D—H1D···O1Ciii0.862.002.857 (4)173.1
Symmetry codes: (i) x+1, y+1, z+1; (ii) x1, y1, z1; (iii) x+1, y+1, z+1.
 

Acknowledgements

ASP thanks the UOM for research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

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First citationOdabaşoğlu, M., Büyükgüngör, O., Sunil, K. & Narayana, B. (2007). Acta Cryst. E63, o4145–o4146.  Web of Science CSD CrossRef IUCr Journals
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