4-(2-Fluoro­benzo­yl)-1-[2-(4-hy­droxy­phen­yl)-2-oxoeth­yl]piperazin-1-ium trifluoro­acetate

Bian, F.; Jin, Y.; Chi, S.; Shi, G.; Xu, S.

doi:10.1107/S1600536812042857

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3243

doi:10.1107/S1600536812042857

Open

access

4-(2-Fluorobenzoyl)-1-[2-(4-hydroxyphenyl)-2-oxoethyl]piperazin-1-ium trifluoroacetate

Fuyong Bian,^a Yi Jin,^a Shaoming Chi,^a Guojun Shi ^a and Sichuan Xu ^a ^*

^aCollege of Chemical Science and Technology, Yunnan University, Kunming City, People's Republic of China
^*Correspondence e-mail: sichuan@ynu.edu.cn

(Received 5 September 2012; accepted 13 October 2012; online 31 October 2012)

In the crystal structure of the title compound, C₁₉H₂₀FN₂O₃⁺·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.

Related 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

C₁₉H₂₀FN₂O₃⁺·C₂F₃O₂⁻
M_r = 456.39
Monoclinic, P 2₁ /n
a = 10.055 (3) Å
b = 9.601 (2) Å
c = 21.946 (5) Å
β = 91.960 (4)°
V = 2117.4 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 298 K
0.23 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.956, T_max = 0.971
12540 measured reflections
3824 independent reflections
1534 reflections with I > 2σ(I)
R_int = 0.070

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.240
S = 1.03
3824 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001); cell refinement: 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812042857/qm2083sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812042857/qm2083Isup2.hkl

checkCIF report

Related literature top

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 top

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 column chromatography 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.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: 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).

Figures top

Fig. 1. Ellipsoid plot

4-(2-Fluorobenzoyl)-1-[2-(4-hydroxyphenyl)-2-oxoethyl]piperazin-1-ium trifluoroacetate top

Crystal data top

C₁₉H₂₀FN₂O₃⁺·C₂F₃O₂⁻	F(000) = 944
M_r = 456.39	D_x = 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

Data collection top

Bruker SMART CCD area-detector diffractometer	3824 independent reflections
Radiation source: fine-focus sealed tube	1534 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
phi and ω scans	θ_max = 25.4°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
T_min = 0.956, T_max = 0.971	k = 0→11
12540 measured reflections	l = 0→16

Refinement top

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(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
3824 reflections	(Δ/σ)_max < 0.001
289 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₉H₂₀FN₂O₃⁺·C₂F₃O₂⁻	V = 2117.4 (9) Å³
M_r = 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)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3824 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1534 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.971	R_int = 0.070
12540 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.240	H-atom parameters constrained
S = 1.03	Δρ_max = 0.26 e Å⁻³
3824 reflections	Δρ_min = −0.20 e Å⁻³
289 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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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⁻
M_r	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)
T_min, T_max	0.956, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	12540, 3824, 1534
R_int	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
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.20

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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

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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3243

doi:10.1107/S1600536812042857

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

4-(2-Fluoro­benzo­yl)-1-[2-(4-hy­dr­oxy­phen­yl)-2-oxoeth­yl]piperazin-1-ium tri­fluoro­acetate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-(2-Fluorobenzoyl)-1-[2-(4-hydroxyphenyl)-2-oxoethyl]piperazin-1-ium trifluoroacetate