4-(2-Fluoro-benzo-yl)-1-[2-(4-hy-droxy-phen-yl)-2-oxoeth-yl]piperazin-1-ium trifluoro-acetate.

In the crystal structure of the title compound, C(19)H(20)FN(2)O(3) (+)·C(2)F(3)O(2) (-), 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 = 456.39

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.240

S = 1.03

3824 reflections

289 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.20 e Å−3

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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812042857/qm2083sup1.cif

Click here for additional data file.

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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

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) ; (ii) .