organic compounds
4-(2-Fluorobenzoyl)-1-[2-(4-hydroxyphenyl)-2-oxoethyl]piperazin-1-ium trifluoroacetate
aCollege of Chemical Science and Technology, Yunnan University, Kunming City, People's Republic of China
*Correspondence e-mail: sichuan@ynu.edu.cn
In the 19H20FN2O3+·C2F3O2−, N—H⋯O and O—H⋯O hydrogen bonds link two cations and two anions into a 22-atom ring. These rings are further linked into a three dimensional network by weak C—H⋯O contacts.
of the title compound, CRelated literature
For the preparation for the title compound, see: Hoff et al. (2005); Wallén et al. (2003); Stachulski et al. (2006). For similar structures, see: Luedtkea & Mach (2003); Rok et al. (2007); Friedel & Crafts (1932a,b). For the applications of similar compounds, see: Wise (1996).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001); data reduction: SAINT; 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.
Supporting information
10.1107/S1600536812042857/qm2083sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812042857/qm2083Isup2.hkl
The title compound was obtained through the following four steps: 2-fluorobenzoic acid (700 mg, 5 mmol) was dissolved into 3 ml of SOCl2, the mixture stirred at 1033 K for 5 h and then slowly cooled to room temperature before removing excess SOCl2. After preparing an ethanol solution (10 ml) of 2-fluorobenzoyl chloride (317 mg, 2 mmol) and 1-boc-piperazine (372 mg, 4 mmol), potassium carbonate (552 mg, 4 mmol) was added to the solution. The mixture was refluxed for 12 h and then cooled to room temperature; extraction and concentration were performed to obtain an oil. After mixing the oil (a dichloromethane solution, 10 ml) with TFA (1.5 ml) and stirring for 12 h to complete the reaction, the mixture was poured into water. The aqueous layer was extracted by ethyl acetate, and then the organic layer was separated, dried using sodium sulfate to obtain 4-(2-fluorobenzoyl)piperazin-1-ium trifluoroacetate. Potassium carbonate (276 mg, 2 mmol) was added to the prepared ethanol solution (10 ml) of (2-fluorophenyl)(piperazin-1-yl)methanone (208 mg, 1 mmol) and 2-chloro-1-(4-hydroxyphenyl)ethanone (341 mg, 2 mmol), which was refluxed for 5 h and mixed by adding water. Again the aqueous layer was extracted by ethyl acetate for the separation of the organic layer, washed using anhydrous ethyl acetate, and dried using sodium sulfate, filtered, and concentrated in vacuum. The purification of residue by using silica gel
and eluting with EtOAc–petroleum ether (1:1) produced the pale-yellow solid (yield: 164 mg, 48%) of 4-(2-fluorobenzoyl)-1-[2-(4-hydroxyphenyl)-2-oxoethyl]piperazin-1-ium trifluoroacetate.Hatomswereplacedincalculatedpositions[C—H=0.93(aromatic) and O—H= 0.82 or0.96Å (methylgroup)]and refined using a ridingmodel approximation withUiso(H) constrainedto1.2 (aromatic) or 1.5(methyl,O—H)timesUeq of therespectiveparentatom.
Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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).C19H20FN2O3+·C2F3O2− | F(000) = 944 |
Mr = 456.39 | Dx = 1.432 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.055 (3) Å | Cell parameters from 892 reflections |
b = 9.601 (2) Å | θ = 2.3–17.0° |
c = 21.946 (5) Å | µ = 0.13 mm−1 |
β = 91.960 (4)° | T = 298 K |
V = 2117.4 (9) Å3 | Parallelepiped, colourless |
Z = 4 | 0.23 × 0.20 × 0.18 mm |
Bruker SMART CCD area-detector diffractometer | 3824 independent reflections |
Radiation source: fine-focus sealed tube | 1534 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.070 |
phi and ω scans | θmax = 25.4°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −12→12 |
Tmin = 0.956, Tmax = 0.971 | k = 0→11 |
12540 measured reflections | l = 0→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.073 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.240 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
3824 reflections | (Δ/σ)max < 0.001 |
289 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C19H20FN2O3+·C2F3O2− | V = 2117.4 (9) Å3 |
Mr = 456.39 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.055 (3) Å | µ = 0.13 mm−1 |
b = 9.601 (2) Å | T = 298 K |
c = 21.946 (5) Å | 0.23 × 0.20 × 0.18 mm |
β = 91.960 (4)° |
Bruker SMART CCD area-detector diffractometer | 3824 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 1534 reflections with I > 2σ(I) |
Tmin = 0.956, Tmax = 0.971 | Rint = 0.070 |
12540 measured reflections |
R[F2 > 2σ(F2)] = 0.073 | 0 restraints |
wR(F2) = 0.240 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.26 e Å−3 |
3824 reflections | Δρmin = −0.20 e Å−3 |
289 parameters |
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 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
F1 | 0.6641 (4) | 0.7921 (4) | 0.35902 (18) | 0.1420 (13) | |
F2 | −0.0352 (4) | 0.0629 (4) | 0.3531 (2) | 0.1733 (18) | |
F3 | −0.0010 (4) | 0.2786 (4) | 0.35550 (19) | 0.1465 (15) | |
F4 | −0.0132 (4) | 0.1720 (4) | 0.27235 (19) | 0.1558 (16) | |
N1 | 0.9794 (3) | 0.7317 (3) | 0.17362 (14) | 0.0623 (9) | |
H1N | 1.0634 | 0.7032 | 0.1657 | 0.081* | |
N2 | 0.9521 (4) | 0.6187 (4) | 0.29247 (17) | 0.0772 (10) | |
O1 | 0.7573 (3) | 0.9834 (3) | −0.15804 (14) | 0.0945 (11) | |
H1 | 0.7304 | 1.0632 | −0.1533 | 0.123* | |
O2 | 1.0042 (3) | 0.6279 (3) | 0.05966 (14) | 0.0850 (9) | |
O3 | 0.7802 (4) | 0.5059 (4) | 0.33367 (18) | 0.1197 (13) | |
O4 | 0.2142 (4) | 0.0147 (4) | 0.3220 (2) | 0.1226 (14) | |
O5 | 0.2540 (3) | 0.2358 (4) | 0.34091 (16) | 0.0951 (11) | |
C1 | 0.7985 (4) | 0.9296 (5) | −0.1033 (2) | 0.0742 (12) | |
C2 | 0.8442 (5) | 0.7938 (5) | −0.1037 (2) | 0.0813 (13) | |
H2 | 0.8444 | 0.7442 | −0.1401 | 0.106* | |
C3 | 0.8891 (4) | 0.7321 (4) | −0.0505 (2) | 0.0753 (12) | |
H3 | 0.9200 | 0.6409 | −0.0512 | 0.098* | |
C4 | 0.8891 (4) | 0.8047 (4) | 0.00491 (19) | 0.0642 (11) | |
C5 | 0.8382 (4) | 0.9385 (4) | 0.0040 (2) | 0.0720 (12) | |
H5 | 0.8336 | 0.9874 | 0.0405 | 0.094* | |
C6 | 0.7943 (4) | 1.0014 (5) | −0.0493 (2) | 0.0766 (12) | |
H6 | 0.7618 | 1.0921 | −0.0488 | 0.100* | |
C7 | 0.9441 (4) | 0.7384 (4) | 0.06037 (19) | 0.0653 (11) | |
C8 | 0.9287 (5) | 0.8139 (4) | 0.12025 (18) | 0.0711 (12) | |
H8A | 0.9763 | 0.9016 | 0.1190 | 0.092* | |
H8B | 0.8353 | 0.8346 | 0.1253 | 0.092* | |
C9 | 0.8978 (5) | 0.6055 (4) | 0.1846 (2) | 0.0846 (14) | |
H9A | 0.8992 | 0.5449 | 0.1493 | 0.110* | |
H9B | 0.8063 | 0.6325 | 0.1908 | 0.110* | |
C10 | 0.9516 (5) | 0.5284 (4) | 0.2399 (2) | 0.0872 (14) | |
H10A | 0.8969 | 0.4473 | 0.2472 | 0.113* | |
H10B | 1.0415 | 0.4968 | 0.2329 | 0.113* | |
C11 | 1.0351 (5) | 0.7411 (4) | 0.28498 (18) | 0.0728 (12) | |
H11A | 1.1268 | 0.7127 | 0.2803 | 0.095* | |
H11B | 1.0314 | 0.7994 | 0.3210 | 0.095* | |
C12 | 0.9874 (4) | 0.8226 (4) | 0.22957 (18) | 0.0684 (11) | |
H12A | 0.9003 | 0.8614 | 0.2368 | 0.089* | |
H12B | 1.0480 | 0.8993 | 0.2228 | 0.089* | |
C13 | 0.8623 (5) | 0.6010 (6) | 0.3364 (2) | 0.0864 (14) | |
C14 | 0.8670 (5) | 0.6952 (5) | 0.3901 (2) | 0.0782 (13) | |
C15 | 0.7657 (6) | 0.7849 (6) | 0.4023 (3) | 0.0935 (15) | |
C16 | 0.7596 (7) | 0.8661 (6) | 0.4533 (3) | 0.1098 (19) | |
H16 | 0.6881 | 0.9251 | 0.4598 | 0.143* | |
C17 | 0.8654 (8) | 0.8552 (7) | 0.4944 (3) | 0.117 (2) | |
H17 | 0.8663 | 0.9095 | 0.5295 | 0.152* | |
C18 | 0.9690 (7) | 0.7671 (8) | 0.4851 (3) | 0.133 (2) | |
H18 | 1.0400 | 0.7609 | 0.5133 | 0.173* | |
C19 | 0.9659 (6) | 0.6875 (7) | 0.4329 (3) | 0.124 (2) | |
H19 | 1.0354 | 0.6255 | 0.4269 | 0.161* | |
C20 | 0.1836 (5) | 0.1356 (6) | 0.3310 (2) | 0.0810 (14) | |
C21 | 0.0321 (5) | 0.1635 (6) | 0.3290 (3) | 0.0932 (15) |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.138 (3) | 0.151 (3) | 0.135 (3) | 0.049 (2) | −0.022 (2) | 0.000 (2) |
F2 | 0.103 (3) | 0.157 (3) | 0.262 (5) | −0.037 (2) | 0.036 (3) | 0.053 (3) |
F3 | 0.120 (3) | 0.135 (3) | 0.185 (4) | 0.039 (2) | 0.010 (3) | −0.046 (3) |
F4 | 0.137 (3) | 0.195 (4) | 0.131 (3) | 0.028 (3) | −0.059 (3) | −0.024 (3) |
N1 | 0.068 (2) | 0.0591 (19) | 0.060 (2) | −0.0027 (16) | 0.0064 (16) | 0.0012 (15) |
N2 | 0.089 (3) | 0.071 (2) | 0.073 (2) | −0.011 (2) | 0.016 (2) | 0.0063 (19) |
O1 | 0.112 (3) | 0.094 (2) | 0.076 (2) | −0.0032 (18) | −0.0173 (19) | 0.0037 (17) |
O2 | 0.099 (2) | 0.075 (2) | 0.081 (2) | 0.0236 (17) | 0.0098 (17) | −0.0025 (16) |
O3 | 0.113 (3) | 0.121 (3) | 0.127 (3) | −0.045 (2) | 0.034 (2) | 0.004 (2) |
O4 | 0.106 (3) | 0.093 (3) | 0.169 (4) | 0.002 (2) | 0.004 (3) | −0.007 (3) |
O5 | 0.088 (2) | 0.093 (2) | 0.104 (3) | −0.0177 (19) | 0.0044 (19) | −0.0028 (19) |
C1 | 0.072 (3) | 0.071 (3) | 0.079 (3) | −0.004 (2) | −0.009 (2) | 0.008 (2) |
C2 | 0.092 (3) | 0.086 (3) | 0.066 (3) | 0.002 (3) | −0.008 (3) | −0.006 (2) |
C3 | 0.078 (3) | 0.067 (3) | 0.082 (3) | −0.001 (2) | 0.013 (2) | −0.009 (2) |
C4 | 0.067 (3) | 0.059 (2) | 0.067 (3) | −0.003 (2) | 0.003 (2) | −0.011 (2) |
C5 | 0.079 (3) | 0.064 (3) | 0.072 (3) | 0.000 (2) | 0.001 (2) | −0.009 (2) |
C6 | 0.076 (3) | 0.073 (3) | 0.080 (3) | −0.001 (2) | −0.002 (2) | 0.000 (2) |
C7 | 0.065 (3) | 0.060 (3) | 0.072 (3) | −0.005 (2) | 0.011 (2) | −0.005 (2) |
C8 | 0.087 (3) | 0.063 (2) | 0.063 (3) | 0.012 (2) | −0.001 (2) | −0.003 (2) |
C9 | 0.097 (3) | 0.068 (3) | 0.088 (3) | −0.030 (3) | 0.010 (3) | −0.002 (2) |
C10 | 0.104 (4) | 0.062 (3) | 0.096 (4) | −0.016 (2) | 0.017 (3) | 0.010 (3) |
C11 | 0.081 (3) | 0.077 (3) | 0.061 (3) | −0.016 (2) | 0.001 (2) | 0.010 (2) |
C12 | 0.077 (3) | 0.064 (2) | 0.064 (3) | −0.004 (2) | 0.004 (2) | −0.004 (2) |
C13 | 0.083 (3) | 0.085 (3) | 0.092 (4) | −0.005 (3) | 0.012 (3) | 0.019 (3) |
C14 | 0.068 (3) | 0.095 (3) | 0.073 (3) | −0.007 (3) | 0.013 (2) | 0.026 (3) |
C15 | 0.090 (4) | 0.099 (4) | 0.091 (4) | 0.010 (3) | 0.003 (3) | 0.029 (3) |
C16 | 0.148 (6) | 0.087 (4) | 0.097 (4) | 0.010 (4) | 0.034 (4) | 0.014 (3) |
C17 | 0.140 (6) | 0.142 (6) | 0.070 (4) | −0.021 (5) | 0.015 (4) | 0.003 (3) |
C18 | 0.095 (5) | 0.203 (7) | 0.102 (5) | 0.026 (5) | 0.004 (4) | 0.006 (5) |
C19 | 0.095 (4) | 0.185 (6) | 0.092 (4) | 0.025 (4) | 0.014 (4) | −0.026 (4) |
C20 | 0.105 (4) | 0.070 (3) | 0.067 (3) | −0.012 (3) | 0.000 (3) | 0.003 (2) |
C21 | 0.078 (3) | 0.098 (4) | 0.104 (4) | 0.001 (3) | −0.001 (3) | 0.000 (3) |
F1—C15 | 1.372 (6) | C6—H6 | 0.9300 |
F2—C21 | 1.301 (6) | C7—C8 | 1.513 (5) |
F3—C21 | 1.298 (6) | C8—H8A | 0.9700 |
F4—C21 | 1.312 (6) | C8—H8B | 0.9700 |
N1—C8 | 1.488 (5) | C9—C10 | 1.505 (6) |
N1—C9 | 1.488 (5) | C9—H9A | 0.9700 |
N1—C12 | 1.506 (5) | C9—H9B | 0.9700 |
N1—H1N | 0.9100 | C10—H10A | 0.9700 |
N2—C13 | 1.353 (6) | C10—H10B | 0.9700 |
N2—C10 | 1.443 (5) | C11—C12 | 1.510 (5) |
N2—C11 | 1.454 (5) | C11—H11A | 0.9700 |
O1—C1 | 1.360 (5) | C11—H11B | 0.9700 |
O1—H1 | 0.8200 | C12—H12A | 0.9700 |
O2—C7 | 1.221 (4) | C12—H12B | 0.9700 |
O3—C13 | 1.231 (5) | C13—C14 | 1.486 (7) |
O4—C20 | 1.219 (5) | C14—C19 | 1.346 (7) |
O5—C20 | 1.209 (5) | C14—C15 | 1.368 (7) |
C1—C6 | 1.373 (6) | C15—C16 | 1.367 (7) |
C1—C2 | 1.382 (6) | C16—C17 | 1.375 (8) |
C2—C3 | 1.372 (6) | C16—H16 | 0.9300 |
C2—H2 | 0.9300 | C17—C18 | 1.363 (8) |
C3—C4 | 1.402 (6) | C17—H17 | 0.9300 |
C3—H3 | 0.9300 | C18—C19 | 1.377 (8) |
C4—C5 | 1.383 (5) | C18—H18 | 0.9300 |
C4—C7 | 1.465 (6) | C19—H19 | 0.9300 |
C5—C6 | 1.376 (6) | C20—C21 | 1.546 (7) |
C5—H5 | 0.9300 | ||
C8—N1—C9 | 112.6 (3) | N2—C10—H10B | 109.7 |
C8—N1—C12 | 110.0 (3) | C9—C10—H10B | 109.7 |
C9—N1—C12 | 110.7 (3) | H10A—C10—H10B | 108.2 |
C8—N1—H1N | 107.8 | N2—C11—C12 | 110.0 (3) |
C9—N1—H1N | 107.8 | N2—C11—H11A | 109.7 |
C12—N1—H1N | 107.8 | C12—C11—H11A | 109.7 |
C13—N2—C10 | 120.7 (4) | N2—C11—H11B | 109.7 |
C13—N2—C11 | 125.5 (4) | C12—C11—H11B | 109.7 |
C10—N2—C11 | 112.4 (3) | H11A—C11—H11B | 108.2 |
C1—O1—H1 | 109.5 | N1—C12—C11 | 111.3 (3) |
O1—C1—C6 | 123.7 (4) | N1—C12—H12A | 109.4 |
O1—C1—C2 | 116.3 (4) | C11—C12—H12A | 109.4 |
C6—C1—C2 | 120.0 (4) | N1—C12—H12B | 109.4 |
C3—C2—C1 | 120.1 (4) | C11—C12—H12B | 109.4 |
C3—C2—H2 | 120.0 | H12A—C12—H12B | 108.0 |
C1—C2—H2 | 120.0 | O3—C13—N2 | 121.4 (5) |
C2—C3—C4 | 121.0 (4) | O3—C13—C14 | 119.5 (5) |
C2—C3—H3 | 119.5 | N2—C13—C14 | 119.0 (5) |
C4—C3—H3 | 119.5 | C19—C14—C15 | 115.9 (5) |
C5—C4—C3 | 117.4 (4) | C19—C14—C13 | 121.5 (5) |
C5—C4—C7 | 123.0 (4) | C15—C14—C13 | 122.3 (5) |
C3—C4—C7 | 119.6 (4) | C16—C15—C14 | 125.0 (6) |
C6—C5—C4 | 121.9 (4) | C16—C15—F1 | 119.0 (6) |
C6—C5—H5 | 119.1 | C14—C15—F1 | 116.0 (5) |
C4—C5—H5 | 119.1 | C15—C16—C17 | 116.0 (6) |
C1—C6—C5 | 119.7 (4) | C15—C16—H16 | 122.0 |
C1—C6—H6 | 120.2 | C17—C16—H16 | 122.0 |
C5—C6—H6 | 120.2 | C18—C17—C16 | 121.8 (6) |
O2—C7—C4 | 122.7 (4) | C18—C17—H17 | 119.1 |
O2—C7—C8 | 119.5 (4) | C16—C17—H17 | 119.1 |
C4—C7—C8 | 117.8 (4) | C17—C18—C19 | 118.2 (6) |
N1—C8—C7 | 112.8 (3) | C17—C18—H18 | 120.9 |
N1—C8—H8A | 109.0 | C19—C18—H18 | 120.9 |
C7—C8—H8A | 109.0 | C14—C19—C18 | 123.0 (6) |
N1—C8—H8B | 109.0 | C14—C19—H19 | 118.5 |
C7—C8—H8B | 109.0 | C18—C19—H19 | 118.5 |
H8A—C8—H8B | 107.8 | O5—C20—O4 | 129.6 (6) |
N1—C9—C10 | 110.3 (4) | O5—C20—C21 | 116.0 (5) |
N1—C9—H9A | 109.6 | O4—C20—C21 | 114.5 (5) |
C10—C9—H9A | 109.6 | F3—C21—F2 | 107.8 (5) |
N1—C9—H9B | 109.6 | F3—C21—F4 | 106.6 (5) |
C10—C9—H9B | 109.6 | F2—C21—F4 | 105.3 (5) |
H9A—C9—H9B | 108.1 | F3—C21—C20 | 113.7 (5) |
N2—C10—C9 | 109.9 (4) | F2—C21—C20 | 112.7 (5) |
N2—C10—H10A | 109.7 | F4—C21—C20 | 110.3 (5) |
C9—C10—H10A | 109.7 | ||
O1—C1—C2—C3 | 179.2 (4) | N2—C11—C12—N1 | −54.0 (5) |
C6—C1—C2—C3 | −2.0 (7) | C10—N2—C13—O3 | 1.8 (7) |
C1—C2—C3—C4 | 0.3 (7) | C11—N2—C13—O3 | 167.4 (4) |
C2—C3—C4—C5 | 2.1 (6) | C10—N2—C13—C14 | 179.3 (4) |
C2—C3—C4—C7 | −176.9 (4) | C11—N2—C13—C14 | −15.1 (7) |
C3—C4—C5—C6 | −2.8 (6) | O3—C13—C14—C19 | 106.7 (6) |
C7—C4—C5—C6 | 176.1 (4) | N2—C13—C14—C19 | −70.8 (6) |
O1—C1—C6—C5 | −180.0 (4) | O3—C13—C14—C15 | −66.8 (7) |
C2—C1—C6—C5 | 1.4 (7) | N2—C13—C14—C15 | 115.7 (5) |
C4—C5—C6—C1 | 1.1 (7) | C19—C14—C15—C16 | 0.8 (8) |
C5—C4—C7—O2 | −170.3 (4) | C13—C14—C15—C16 | 174.7 (5) |
C3—C4—C7—O2 | 8.6 (6) | C19—C14—C15—F1 | −179.4 (5) |
C5—C4—C7—C8 | 7.6 (6) | C13—C14—C15—F1 | −5.6 (7) |
C3—C4—C7—C8 | −173.5 (4) | C14—C15—C16—C17 | 0.6 (8) |
C9—N1—C8—C7 | −67.6 (4) | F1—C15—C16—C17 | −179.1 (5) |
C12—N1—C8—C7 | 168.4 (3) | C15—C16—C17—C18 | −1.0 (9) |
O2—C7—C8—N1 | −6.2 (6) | C16—C17—C18—C19 | 0.0 (10) |
C4—C7—C8—N1 | 175.8 (3) | C15—C14—C19—C18 | −1.9 (9) |
C8—N1—C9—C10 | −178.6 (4) | C13—C14—C19—C18 | −175.8 (6) |
C12—N1—C9—C10 | −55.1 (5) | C17—C18—C19—C14 | 1.6 (11) |
C13—N2—C10—C9 | 106.7 (5) | O5—C20—C21—F3 | −19.3 (7) |
C11—N2—C10—C9 | −60.7 (5) | O4—C20—C21—F3 | 160.9 (5) |
N1—C9—C10—N2 | 58.3 (5) | O5—C20—C21—F2 | −142.4 (5) |
C13—N2—C11—C12 | −108.2 (5) | O4—C20—C21—F2 | 37.8 (7) |
C10—N2—C11—C12 | 58.4 (5) | O5—C20—C21—F4 | 100.3 (5) |
C8—N1—C12—C11 | 178.4 (3) | O4—C20—C21—F4 | −79.5 (6) |
C9—N1—C12—C11 | 53.4 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O5i | 0.91 | 1.87 | 2.710 (5) | 152 |
O1—H1···O5ii | 0.82 | 1.95 | 2.697 (5) | 151 |
C8—H8B···O3i | 0.97 | 2.22 | 2.996 (6) | 136 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) x+1/2, −y+3/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C19H20FN2O3+·C2F3O2− |
Mr | 456.39 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 10.055 (3), 9.601 (2), 21.946 (5) |
β (°) | 91.960 (4) |
V (Å3) | 2117.4 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.13 |
Crystal size (mm) | 0.23 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.956, 0.971 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12540, 3824, 1534 |
Rint | 0.070 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.073, 0.240, 1.03 |
No. of reflections | 3824 |
No. of parameters | 289 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.20 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O5i | 0.91 | 1.87 | 2.710 (5) | 152.0 |
O1—H1···O5ii | 0.82 | 1.95 | 2.697 (5) | 151.1 |
C8—H8B···O3i | 0.97 | 2.22 | 2.996 (6) | 136.0 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) x+1/2, −y+3/2, z−1/2. |
Acknowledgements
Support from the National Natural Science Foundation of China (21163024) is acknowledged.
References
Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Friedel, C. & Crafts, J. M. (1932a). Compt. Rend. 84, 1392–1395. Google Scholar
Friedel, C. & Crafts, J. M. (1932b). Compt. Rend. 84, 1450–1450. Google Scholar
Hoff, B., Strandberg, E., Ulrich, A. S., Tieleman, D. P. & Posten, C. (2005). Biophys. J. 88, 1818–1827. Web of Science CrossRef PubMed CAS Google Scholar
Luedtkea, R. R. & Mach, R. H. (2003). Curr. Pharm. Des. 9, 643–671. Web of Science PubMed Google Scholar
Rok, F., Stanislav, G. & Danijel, K. (2007). Tetrahedron, 63, 10698–10708. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stachulski, A. V., Berry, N. G., Low, A. C. L., Moores, S. L., Row, E., Warhurst, D. C., Adagu, I. S. & Rossignol, J.-F. (2006). J. Med. Chem. 49, 1450–1454. Web of Science CrossRef PubMed CAS Google Scholar
Wallén, E. A. A., Christiaans, J. A. M., Jarho, E. M., Forsberg, M. M., Venäläinen, J. I., Mannisto, P. T. & Gynther, J. (2003). J. Med. Chem. 46, 4543–4551. Web of Science PubMed Google Scholar
Wise, R. A. (1996). Curr Opin Neurobiol. 6, 243–251. CrossRef CAS PubMed Web of Science Google Scholar
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