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

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ISSN: 2056-9890

(E)-3-(2-Eth­­oxy­phen­yl)-1-{4-[(2-fluoro­phen­yl)(4-fluoro­phen­yl)meth­yl]piperazin-1-yl}prop-2-en-1-one

aSchool of Chemistry and Chemical Engineering, Southeast University, Sipailou No. 2 Nanjing, Nanjing 210096, People's Republic of China, and bSchool of Pharmacy, Nanjing Medical University, Hanzhong Road No. 140 Nanjing, Nanjing 210029, People's Republic of China
*Correspondence e-mail: wubin@njmu.edu.cn

(Received 21 May 2012; accepted 26 May 2012; online 31 May 2012)

In the title compound, C28H28F2N2O2, the piperazine ring has a chair conformation with the pendant N—C bonds in equatorial orientations. The C=C double bond has an E conformation and the dihedral angle between the fluoro­benzene rings is 70.8 (3)°. In the crystal, mol­ecules are linked by C—H⋯O and C—H⋯F hydrogen bonds.

Related literature

For a related structure and background to cinnamic acid derivatives, see: Teng et al. (2011[Teng, Y.-B., Dai, Z.-H. & Wu, B. (2011). Acta Cryst. E67, o697.]); Zhong et al. (2012[Zhong, Y., Zhang, X. P. & Wu, B. (2012). Acta Cryst. E68, o298.]). For further synthetic details, see: Wu et al. (2008[Wu, B., Zhou, L. & Cai, H.-H. (2008). Chin. Chem. Lett. 19, 1163-1166.]).

[Scheme 1]

Experimental

Crystal data
  • C28H28F2N2O2

  • Mr = 462.52

  • Orthorhombic, P 21 21 21

  • a = 8.8550 (18) Å

  • b = 12.827 (3) Å

  • c = 22.432 (5) Å

  • V = 2547.9 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.975, Tmax = 0.992

  • 5217 measured reflections

  • 2677 independent reflections

  • 1328 reflections with I > 2σ(I)

  • Rint = 0.092

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.063

  • wR(F2) = 0.160

  • S = 1.00

  • 2677 reflections

  • 307 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.12 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C5—H5A⋯O1i 0.93 2.44 3.316 (6) 156
C15—H15A⋯F2ii 0.97 2.36 3.241 (6) 150
C25—H25A⋯F1iii 0.93 2.55 3.166 (7) 124
Symmetry codes: (i) x, y-1, z; (ii) [-x+{\script{3\over 2}}, -y, z-{\script{1\over 2}}]; (iii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: SHELXL97.

Supporting information


Comment top

As a continuation of our study of cinnamic acid derivatives (Teng et al., 2011; Zhong et al., 2012), we present here the title compound (I). In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in related compounds (Teng et al., 2011; Zhong et al., 2012). The molecule of (I) exists an E configulation with respect to the C19=C20 ethene bond [1.296 (6)]. The piperazine ring adopts a chair conformation with puchering parameters Q = 0.498 (6), Theta = 8.6 (6), Phi = 136 (4). The molecular structure is stabilized by intramolecular C—H···O and C—H···F hydrogen bonds. In the crystal, molecules are linked by intermolecular C—H···O and C—H···F hydrogen bonds.

Related literature top

For a related structure and background to cinnamic acid derivatives, see: Teng et al. (2011); Zhong et al. (2012). For further synthetic details, see: Wu et al. (2008).

Experimental top

The synthesis follows the method of Wu et al. (2008). The title compound was prepared by stirring a mixture of (E)-3-(2-ethoxyphenyl)acrylic acid (0.769 g; 4 mmol), thionyl chloride (2 ml) and dichloromethane (30 ml) for 6 h at room temperature. The solvent was removed under reduced pressure. The residue was dissolved in acetone (15 ml) and reacted with 1-((2-fluorophenyl)(4-fluorophenyl)methyl)piperazine (1.730 g; 6 mmol) in the presence of triethylamine (5 ml) for 12 h at room temperature. The resultant mixture was cooled. The solid, (E)-3-(2-ethoxyphenyl)-1-(4-((2- fluorophenyl)(4-fluorophenyl)methyl)piperazin-1-yl)prop-2-en-1-one obtained was filtered and was recrystallized from ethanol. The colorless single crystals of the title compound used in x-ray diffraction studies were grown in ethanol by a slow evaporation at room temperature.

Refinement top

The absolution structure was indeterminate in the present experiment and Friedel pairs were merged. The arbitrarily assigined chirality of the stereogenic centre is C1 S*. All non-hydrogen atoms were refined anisotropically. All hydrogen atoms were positioned geometrically with C—H distances ranging from 0.93 Å to 0.98 Å and refined as riding on their parent atoms with Uĩso~(H) = 1.2 or 1.5U~eq~ of the carrier atom.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with displacement ellipsoids for non-H drawn at 70% probability level.
[Figure 2] Fig. 2. Packing diagram of the title compound.
(E)-3-(2-Ethoxyphenyl)-1-{4-[(2-fluorophenyl)(4- fluorophenyl)methyl]piperazin-1-yl}prop-2-en-1-one top
Crystal data top
C28H28F2N2O2Dx = 1.206 Mg m3
Mr = 462.52Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 8.8550 (18) Åθ = 9–13°
b = 12.827 (3) ŵ = 0.09 mm1
c = 22.432 (5) ÅT = 293 K
V = 2547.9 (9) Å3Block, colorless
Z = 40.30 × 0.20 × 0.10 mm
F(000) = 976
Data collection top
Enraf–Nonius CAD-4
diffractometer
1328 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.092
Graphite monochromatorθmax = 25.5°, θmin = 1.8°
ω/2θ scansh = 010
Absorption correction: ψ scan
(North et al., 1968)
k = 015
Tmin = 0.975, Tmax = 0.992l = 2727
5217 measured reflections3 standard reflections every 200 reflections
2677 independent reflections intensity decay: 1%
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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.063P)2]
where P = (Fo2 + 2Fc2)/3
2677 reflections(Δ/σ)max < 0.001
307 parametersΔρmax = 0.23 e Å3
1 restraintΔρmin = 0.12 e Å3
Crystal data top
C28H28F2N2O2V = 2547.9 (9) Å3
Mr = 462.52Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.8550 (18) ŵ = 0.09 mm1
b = 12.827 (3) ÅT = 293 K
c = 22.432 (5) Å0.30 × 0.20 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
1328 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.092
Tmin = 0.975, Tmax = 0.9923 standard reflections every 200 reflections
5217 measured reflections intensity decay: 1%
2677 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0631 restraint
wR(F2) = 0.160H-atom parameters constrained
S = 1.00Δρmax = 0.23 e Å3
2677 reflectionsΔρmin = 0.12 e Å3
307 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*/Ueq
O10.7258 (5)0.3977 (2)0.63108 (15)0.0891 (11)
N10.7411 (6)0.0370 (2)0.69576 (16)0.0739 (10)
F11.0297 (5)0.2050 (3)0.6989 (2)0.1490 (16)
C10.8192 (7)0.0465 (4)0.7234 (2)0.0846 (16)
H1A0.92740.03830.71540.102*
O20.7460 (6)0.6004 (3)0.46140 (16)0.1160 (13)
F20.7518 (6)0.0447 (3)0.97218 (14)0.1447 (15)
N20.6907 (7)0.2261 (3)0.63068 (19)0.113 (2)
C20.7675 (8)0.1522 (3)0.6976 (2)0.0780 (15)
C30.6258 (10)0.1824 (6)0.6896 (3)0.109 (2)
H3A0.54660.13670.69720.131*
C40.5969 (12)0.2819 (9)0.6698 (3)0.140 (3)
H4A0.49760.30380.66470.168*
C50.7119 (15)0.3482 (4)0.6578 (3)0.132 (4)
H5A0.68930.41500.64430.159*
C60.8589 (12)0.3209 (8)0.6649 (4)0.146 (4)
H6A0.93840.36560.65590.175*
C70.8803 (9)0.2219 (7)0.6862 (3)0.105 (2)
C80.7955 (9)0.0479 (4)0.7912 (3)0.0894 (18)
C90.9141 (8)0.0567 (5)0.8273 (4)0.105 (2)
H9A1.00920.06540.81040.126*
C100.9031 (10)0.0537 (6)0.8849 (4)0.111 (2)
H10A0.99010.05600.90810.133*
C110.7695 (11)0.0476 (4)0.9110 (3)0.0878 (16)
C120.6397 (8)0.0441 (5)0.8813 (3)0.1040 (19)
H12A0.54710.04320.90080.125*
C130.6508 (8)0.0417 (5)0.8162 (3)0.0949 (18)
H13A0.56520.03630.79240.114*
C140.7528 (7)0.0413 (3)0.6316 (2)0.0761 (13)
H14A0.72350.02560.61520.091*
H14B0.85740.05360.62080.091*
C150.6571 (8)0.1243 (4)0.6045 (2)0.101 (2)
H15A0.67510.12680.56180.121*
H15B0.55140.10770.61080.121*
C160.6743 (8)0.2221 (4)0.6953 (2)0.106 (2)
H16A0.70910.28730.71240.127*
H16B0.56840.21400.70530.127*
C170.7575 (8)0.1385 (3)0.7205 (2)0.0914 (17)
H17A0.73100.13440.76240.110*
H17B0.86370.15680.71840.110*
C180.7198 (8)0.3163 (4)0.6033 (2)0.0939 (19)
C190.7188 (7)0.3198 (4)0.5371 (2)0.0975 (19)
H19A0.71150.25750.51600.117*
C200.7279 (7)0.4064 (3)0.5076 (2)0.0801 (14)
H20A0.73120.46690.53040.096*
C210.7336 (6)0.4210 (3)0.4434 (2)0.0707 (12)
C220.7270 (9)0.3415 (4)0.4028 (2)0.102 (2)
H22A0.71670.27380.41700.123*
C230.7348 (8)0.3568 (5)0.3411 (3)0.1042 (17)
H23A0.73310.30050.31500.125*
C240.7448 (7)0.4536 (5)0.3208 (2)0.0986 (17)
H24A0.74950.46500.27990.118*
C250.7485 (7)0.5382 (4)0.3591 (2)0.0975 (16)
H25A0.75400.60550.34380.117*
C260.7439 (7)0.5228 (4)0.4206 (2)0.0794 (13)
C270.7553 (18)0.7032 (5)0.4448 (3)0.213 (5)
H27A0.66880.72170.42050.255*
H27B0.84610.71450.42140.255*
C280.759 (2)0.7692 (5)0.4994 (5)0.269 (8)
H28A0.77020.84100.48820.403*
H28B0.84280.74870.52390.403*
H28C0.66670.76030.52120.403*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.134 (3)0.0448 (16)0.088 (2)0.009 (2)0.015 (3)0.0009 (17)
N10.129 (3)0.0314 (16)0.061 (2)0.001 (3)0.015 (3)0.0062 (15)
F10.148 (3)0.102 (3)0.197 (4)0.038 (3)0.015 (3)0.023 (3)
C10.126 (4)0.059 (3)0.069 (3)0.017 (3)0.009 (3)0.001 (3)
O20.209 (4)0.0492 (18)0.090 (2)0.002 (3)0.014 (4)0.0069 (18)
F20.249 (4)0.117 (2)0.068 (2)0.020 (4)0.015 (3)0.0211 (18)
N20.238 (6)0.0337 (19)0.067 (3)0.002 (3)0.012 (3)0.0035 (19)
C20.127 (5)0.042 (2)0.065 (3)0.003 (4)0.000 (4)0.004 (2)
C30.145 (6)0.099 (5)0.083 (4)0.012 (5)0.009 (5)0.019 (4)
C40.189 (8)0.134 (8)0.098 (6)0.044 (7)0.042 (5)0.021 (6)
C50.288 (13)0.036 (3)0.072 (4)0.000 (6)0.044 (7)0.007 (3)
C60.217 (10)0.113 (7)0.108 (6)0.111 (7)0.026 (7)0.020 (5)
C70.127 (5)0.120 (6)0.068 (4)0.027 (5)0.016 (4)0.018 (4)
C80.152 (6)0.041 (2)0.075 (4)0.015 (3)0.004 (4)0.011 (2)
C90.119 (5)0.071 (4)0.124 (7)0.006 (4)0.011 (5)0.008 (4)
C100.152 (7)0.094 (5)0.088 (5)0.003 (5)0.026 (5)0.015 (4)
C110.131 (5)0.057 (3)0.076 (4)0.007 (4)0.019 (5)0.013 (3)
C120.121 (5)0.080 (4)0.110 (6)0.007 (4)0.006 (5)0.008 (4)
C130.129 (5)0.068 (3)0.087 (5)0.028 (4)0.029 (4)0.002 (4)
C140.124 (4)0.040 (2)0.064 (3)0.016 (3)0.010 (3)0.001 (2)
C150.176 (6)0.061 (3)0.066 (3)0.004 (4)0.013 (3)0.002 (3)
C160.211 (7)0.055 (3)0.050 (3)0.017 (4)0.006 (4)0.001 (3)
C170.163 (5)0.045 (2)0.066 (3)0.042 (4)0.015 (4)0.001 (2)
C180.172 (6)0.041 (2)0.069 (3)0.016 (4)0.025 (4)0.002 (2)
C190.173 (6)0.047 (2)0.073 (3)0.001 (4)0.010 (4)0.001 (2)
C200.120 (4)0.047 (2)0.073 (3)0.000 (3)0.001 (3)0.010 (2)
C210.089 (3)0.056 (3)0.067 (3)0.007 (3)0.003 (3)0.007 (2)
C220.162 (6)0.062 (3)0.083 (4)0.001 (4)0.038 (5)0.002 (3)
C230.135 (5)0.084 (4)0.094 (4)0.002 (4)0.001 (5)0.008 (3)
C240.121 (4)0.095 (4)0.080 (3)0.027 (5)0.011 (4)0.006 (3)
C250.136 (4)0.078 (3)0.078 (3)0.006 (5)0.015 (4)0.025 (3)
C260.106 (4)0.060 (3)0.072 (3)0.007 (4)0.001 (4)0.009 (2)
C270.456 (17)0.060 (4)0.122 (6)0.052 (9)0.010 (10)0.022 (4)
C280.60 (2)0.067 (4)0.137 (7)0.016 (10)0.001 (13)0.008 (5)
Geometric parameters (Å, º) top
O1—C181.216 (5)C13—H13A0.9300
N1—C11.417 (6)C14—C151.490 (7)
N1—C171.423 (5)C14—H14A0.9700
N1—C141.444 (6)C14—H14B0.9700
F1—C71.371 (8)C15—H15A0.9700
C1—C81.536 (7)C15—H15B0.9700
C1—C21.545 (7)C16—C171.417 (7)
C1—H1A0.9800C16—H16A0.9700
O2—C261.351 (6)C16—H16B0.9700
O2—C271.374 (7)C17—H17A0.9700
F2—C111.383 (7)C17—H17B0.9700
N2—C181.335 (7)C18—C191.488 (7)
N2—C161.458 (6)C19—C201.296 (6)
N2—C151.463 (7)C19—H19A0.9300
C2—C31.325 (9)C20—C211.452 (6)
C2—C71.365 (9)C20—H20A0.9300
C3—C41.375 (12)C21—C221.368 (7)
C3—H3A0.9300C21—C261.406 (6)
C4—C51.354 (13)C22—C231.401 (7)
C4—H4A0.9300C22—H22A0.9300
C5—C61.358 (12)C23—C241.325 (8)
C5—H5A0.9300C23—H23A0.9300
C6—C71.370 (12)C24—C251.385 (7)
C6—H6A0.9300C24—H24A0.9300
C8—C91.331 (8)C25—C261.394 (7)
C8—C131.401 (9)C25—H25A0.9300
C9—C101.296 (8)C27—C281.489 (11)
C9—H9A0.9300C27—H27A0.9700
C10—C111.323 (9)C27—H27B0.9700
C10—H10A0.9300C28—H28A0.9600
C11—C121.328 (8)C28—H28B0.9600
C12—C131.463 (8)C28—H28C0.9600
C12—H12A0.9300
C1—N1—C17118.1 (4)N2—C15—H15A109.5
C1—N1—C14115.4 (4)C14—C15—H15A109.5
C17—N1—C14110.2 (3)N2—C15—H15B109.5
N1—C1—C8112.0 (4)C14—C15—H15B109.5
N1—C1—C2110.8 (4)H15A—C15—H15B108.0
C8—C1—C2108.7 (4)C17—C16—N2111.8 (5)
N1—C1—H1A108.4C17—C16—H16A109.3
C8—C1—H1A108.4N2—C16—H16A109.3
C2—C1—H1A108.4C17—C16—H16B109.3
C26—O2—C27121.6 (5)N2—C16—H16B109.3
C18—N2—C16120.4 (4)H16A—C16—H16B107.9
C18—N2—C15129.0 (4)C16—C17—N1118.9 (5)
C16—N2—C15110.4 (4)C16—C17—H17A107.6
C3—C2—C7118.5 (6)N1—C17—H17A107.6
C3—C2—C1126.0 (6)C16—C17—H17B107.6
C7—C2—C1115.3 (6)N1—C17—H17B107.6
C2—C3—C4119.4 (7)H17A—C17—H17B107.0
C2—C3—H3A120.3O1—C18—N2121.2 (4)
C4—C3—H3A120.3O1—C18—C19119.1 (4)
C5—C4—C3120.5 (9)N2—C18—C19118.9 (4)
C5—C4—H4A119.7C20—C19—C18122.4 (5)
C3—C4—H4A119.7C20—C19—H19A118.8
C4—C5—C6122.4 (8)C18—C19—H19A118.8
C4—C5—H5A118.8C19—C20—C21128.2 (5)
C6—C5—H5A118.8C19—C20—H20A115.9
C5—C6—C7114.4 (7)C21—C20—H20A115.9
C5—C6—H6A122.8C22—C21—C26116.9 (4)
C7—C6—H6A122.8C22—C21—C20124.2 (4)
C2—C7—C6124.8 (8)C26—C21—C20118.9 (4)
C2—C7—F1124.3 (7)C21—C22—C23123.5 (5)
C6—C7—F1110.7 (8)C21—C22—H22A118.3
C9—C8—C13118.9 (6)C23—C22—H22A118.3
C9—C8—C1119.7 (7)C24—C23—C22118.3 (6)
C13—C8—C1121.4 (6)C24—C23—H23A120.8
C10—C9—C8123.0 (7)C22—C23—H23A120.8
C10—C9—H9A118.5C23—C24—C25121.5 (5)
C8—C9—H9A118.5C23—C24—H24A119.3
C9—C10—C11120.7 (7)C25—C24—H24A119.3
C9—C10—H10A119.7C24—C25—C26120.2 (5)
C11—C10—H10A119.7C24—C25—H25A119.9
C10—C11—C12123.6 (6)C26—C25—H25A119.9
C10—C11—F2122.9 (7)O2—C26—C25124.4 (4)
C12—C11—F2113.5 (8)O2—C26—C21116.0 (4)
C11—C12—C13116.3 (6)C25—C26—C21119.6 (5)
C11—C12—H12A121.9O2—C27—C28108.9 (6)
C13—C12—H12A121.9O2—C27—H27A109.9
C8—C13—C12117.4 (6)C28—C27—H27A109.9
C8—C13—H13A121.3O2—C27—H27B109.9
C12—C13—H13A121.3C28—C27—H27B109.9
N1—C14—C15113.2 (4)H27A—C27—H27B108.3
N1—C14—H14A108.9C27—C28—H28A109.5
C15—C14—H14A108.9C27—C28—H28B109.5
N1—C14—H14B108.9H28A—C28—H28B109.5
C15—C14—H14B108.9C27—C28—H28C109.5
H14A—C14—H14B107.8H28A—C28—H28C109.5
N2—C15—C14110.9 (5)H28B—C28—H28C109.5
C17—N1—C1—C848.9 (7)C1—N1—C14—C15174.5 (5)
C14—N1—C1—C8177.6 (5)C17—N1—C14—C1548.4 (7)
C17—N1—C1—C2170.4 (5)C18—N2—C15—C14130.6 (7)
C14—N1—C1—C256.1 (6)C16—N2—C15—C1455.2 (8)
N1—C1—C2—C347.6 (8)N1—C14—C15—N255.0 (7)
C8—C1—C2—C375.9 (7)C18—N2—C16—C17133.4 (7)
N1—C1—C2—C7137.0 (5)C15—N2—C16—C1751.8 (8)
C8—C1—C2—C799.5 (6)N2—C16—C17—N149.8 (9)
C7—C2—C3—C40.4 (10)C1—N1—C17—C16176.9 (6)
C1—C2—C3—C4175.6 (6)C14—N1—C17—C1647.4 (8)
C2—C3—C4—C50.9 (11)C16—N2—C18—O13.7 (11)
C3—C4—C5—C60.4 (12)C15—N2—C18—O1170.0 (7)
C4—C5—C6—C71.3 (12)C16—N2—C18—C19173.2 (6)
C3—C2—C7—C62.4 (10)C15—N2—C18—C190.5 (11)
C1—C2—C7—C6178.1 (7)O1—C18—C19—C201.8 (11)
C3—C2—C7—F1172.3 (6)N2—C18—C19—C20171.5 (7)
C1—C2—C7—F13.4 (8)C18—C19—C20—C21177.6 (6)
C5—C6—C7—C22.8 (12)C19—C20—C21—C221.4 (11)
C5—C6—C7—F1172.5 (7)C19—C20—C21—C26179.8 (7)
N1—C1—C8—C9131.1 (6)C26—C21—C22—C232.1 (11)
C2—C1—C8—C9106.2 (7)C20—C21—C22—C23179.0 (7)
N1—C1—C8—C1349.9 (7)C21—C22—C23—C242.0 (13)
C2—C1—C8—C1372.9 (7)C22—C23—C24—C250.4 (12)
C13—C8—C9—C104.2 (10)C23—C24—C25—C260.9 (11)
C1—C8—C9—C10176.8 (6)C27—O2—C26—C251.0 (12)
C8—C9—C10—C113.9 (12)C27—O2—C26—C21179.8 (9)
C9—C10—C11—C120.0 (11)C24—C25—C26—O2179.6 (6)
C9—C10—C11—F2179.7 (6)C24—C25—C26—C210.8 (11)
C10—C11—C12—C133.2 (9)C22—C21—C26—O2178.2 (6)
F2—C11—C12—C13177.1 (5)C20—C21—C26—O20.7 (9)
C9—C8—C13—C120.7 (9)C22—C21—C26—C250.7 (10)
C1—C8—C13—C12179.8 (5)C20—C21—C26—C25179.6 (6)
C11—C12—C13—C82.7 (9)C26—O2—C27—C28178.7 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5A···O1i0.932.443.316 (6)156
C15—H15A···F2ii0.972.363.241 (6)150
C25—H25A···F1iii0.932.553.166 (7)124
Symmetry codes: (i) x, y1, z; (ii) x+3/2, y, z1/2; (iii) x1/2, y+1/2, z+1.

Experimental details

Crystal data
Chemical formulaC28H28F2N2O2
Mr462.52
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)8.8550 (18), 12.827 (3), 22.432 (5)
V3)2547.9 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.975, 0.992
No. of measured, independent and
observed [I > 2σ(I)] reflections
5217, 2677, 1328
Rint0.092
(sin θ/λ)max1)0.605
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.160, 1.00
No. of reflections2677
No. of parameters307
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.12

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5A···O1i0.932.443.316 (6)156
C15—H15A···F2ii0.972.363.241 (6)150
C25—H25A···F1iii0.932.553.166 (7)124
Symmetry codes: (i) x, y1, z; (ii) x+3/2, y, z1/2; (iii) x1/2, y+1/2, z+1.
 

Acknowledgements

The authors thank Professor Hua-Qin Wang of the Analysis Centre, Nanjing University, for the diffraction measurements. This work was supported by the Natural Science Foundation of Jiangsu Province (grant No. BK2010538).

References

First citationEnraf–Nonius (1989). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.  Google Scholar
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTeng, Y.-B., Dai, Z.-H. & Wu, B. (2011). Acta Cryst. E67, o697.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationWu, B., Zhou, L. & Cai, H.-H. (2008). Chin. Chem. Lett. 19, 1163–1166.  Web of Science CrossRef CAS Google Scholar
First citationZhong, Y., Zhang, X. P. & Wu, B. (2012). Acta Cryst. E68, o298.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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