1-{4-[Bis(4-fluoro-phen-yl)meth-yl]piperazin-1-yl}ethanone.

In the title compound, C(19)H(20)F(2)N(2)O, the six-membered piperazine group adopts a slightly distorted chair conformation. The dihedral angle between the mean planes of the two benzene rings is 73.4 (6)°. The mean plane of the ethanone group is twisted from the mean planes of the two benzene rings by 66.7 (8) and 86.2 (6)°. In the crystal, C-H⋯O and C-H⋯F inter-actions link the molecules, forming a three-dimensional structure.

Related literature

For the biological activity of piperazines, see: Bogatcheva et al. (2006 ▶); Brockunier et al. (2004 ▶). For a review of pharmacological and toxicological information for piperazine derivatives, see: Elliott (2011 ▶). For related structures, see: Betz et al. (2011a ▶,b ▶); Dai et al. (2012 ▶); Dayananda et al. (2012a ▶,b ▶); Zhong et al. (2011 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For reference bond-length data, see Allen et al. (1987 ▶).

Experimental

Crystal data

C19H20F2N2O

M = 330.37

Monoclinic,

a = 10.1701 (5) Å

b = 16.5521 (5) Å

c = 11.1690 (5) Å

β = 114.690 (5)°

V = 1708.27 (14) Å3

Z = 4

Cu Kα radiation

μ = 0.79 mm−1

T = 173 K

0.48 × 0.32 × 0.22 mm

Data collection

Oxford Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.802, T max = 1.000

10536 measured reflections

3297 independent reflections

2809 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.155

S = 1.04

3297 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812028097/zj2086sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028097/zj2086Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812028097/zj2086Isup3.cml

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

C19H20F2N2O	F(000) = 696
Mr = 330.37	Dx = 1.285 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 4103 reflections
a = 10.1701 (5) Å	θ = 4.4–71.2°
b = 16.5521 (5) Å	µ = 0.79 mm−1
c = 11.1690 (5) Å	T = 173 K
β = 114.690 (5)°	Chunk, colourless
V = 1708.27 (14) Å3	0.48 × 0.32 × 0.22 mm
Z = 4

Oxford Xcalibur Eos Gemini diffractometer	3297 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2809 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 16.1500 pixels mm-1	θmax = 71.4°, θmin = 5.0°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −12→20
Tmin = 0.802, Tmax = 1.000	l = −13→13
10536 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0781P)2 + 0.7598P] where P = (Fo2 + 2Fc2)/3
3297 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

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.

	x	y	z	Uiso*/Ueq
F1	0.5160 (2)	0.80482 (10)	−0.24955 (14)	0.0811 (5)
F2	0.86017 (18)	1.06144 (9)	0.55722 (15)	0.0788 (5)
O1	0.29530 (17)	0.50309 (9)	0.41107 (15)	0.0534 (4)
N1	0.40533 (18)	0.62266 (10)	0.42534 (15)	0.0410 (4)
N2	0.48228 (15)	0.75448 (8)	0.30161 (13)	0.0304 (3)
C1	0.3741 (3)	0.57161 (13)	0.6169 (2)	0.0520 (5)
H1A	0.3212	0.5298	0.6371	0.078*
H1B	0.3382	0.6234	0.6280	0.078*
H1C	0.4749	0.5674	0.6752	0.078*
C2	0.3555 (2)	0.56254 (11)	0.47665 (19)	0.0395 (4)
C3	0.3933 (2)	0.61611 (12)	0.29096 (19)	0.0465 (5)
H3A	0.3142	0.5801	0.2406	0.056*
H3B	0.4819	0.5935	0.2922	0.056*
C4	0.3666 (2)	0.69801 (12)	0.22666 (17)	0.0406 (4)
H4A	0.3605	0.6930	0.1380	0.049*
H4B	0.2749	0.7189	0.2206	0.049*
C5	0.4817 (2)	0.76336 (11)	0.43201 (17)	0.0363 (4)
H5A	0.3886	0.7842	0.4222	0.044*
H5B	0.5555	0.8019	0.4835	0.044*
C6	0.5101 (2)	0.68390 (12)	0.50348 (18)	0.0426 (5)
H6A	0.6072	0.6658	0.5213	0.051*
H6B	0.5038	0.6909	0.5872	0.051*
C7	0.46380 (18)	0.83174 (11)	0.23205 (16)	0.0333 (4)
H7	0.3663	0.8519	0.2120	0.040*
C8	0.47860 (19)	0.82157 (11)	0.10209 (17)	0.0356 (4)
C9	0.5661 (2)	0.76331 (12)	0.0844 (2)	0.0430 (4)
H9	0.6165	0.7276	0.1526	0.052*
C10	0.5799 (2)	0.75726 (12)	−0.0344 (2)	0.0508 (5)
H10	0.6388	0.7181	−0.0465	0.061*
C11	0.5044 (3)	0.81058 (13)	−0.1324 (2)	0.0522 (5)
C12	0.4182 (3)	0.86953 (15)	−0.1176 (2)	0.0576 (6)
H12	0.3689	0.9055	−0.1856	0.069*
C13	0.4060 (2)	0.87437 (13)	0.00127 (19)	0.0472 (5)
H13	0.3477	0.9141	0.0129	0.057*
C14	0.5726 (2)	0.89431 (11)	0.31739 (16)	0.0349 (4)
C15	0.5244 (2)	0.96762 (12)	0.34201 (19)	0.0426 (4)
H15	0.4259	0.9791	0.3044	0.051*
C16	0.6209 (3)	1.02416 (12)	0.4218 (2)	0.0522 (5)
H16	0.5883	1.0736	0.4384	0.063*
C17	0.7645 (3)	1.00628 (13)	0.4757 (2)	0.0507 (5)
C18	0.8181 (2)	0.93527 (13)	0.4525 (2)	0.0496 (5)
H18	0.9171	0.9251	0.4897	0.060*
C19	0.7207 (2)	0.87896 (12)	0.37212 (19)	0.0419 (4)
H19	0.7546	0.8303	0.3544	0.050*

	U11	U22	U33	U12	U13	U23
F1	0.1304 (14)	0.0839 (11)	0.0563 (9)	0.0159 (10)	0.0658 (9)	0.0004 (7)
F2	0.0951 (11)	0.0602 (9)	0.0724 (10)	−0.0414 (8)	0.0264 (8)	−0.0204 (7)
O1	0.0659 (9)	0.0428 (8)	0.0519 (8)	−0.0214 (7)	0.0250 (7)	−0.0029 (6)
N1	0.0530 (9)	0.0380 (8)	0.0314 (8)	−0.0133 (7)	0.0170 (7)	−0.0030 (6)
N2	0.0345 (7)	0.0299 (7)	0.0268 (7)	−0.0034 (6)	0.0128 (6)	−0.0012 (5)
C1	0.0722 (14)	0.0438 (11)	0.0454 (11)	−0.0056 (10)	0.0300 (10)	0.0073 (9)
C2	0.0417 (9)	0.0368 (10)	0.0405 (10)	−0.0024 (8)	0.0177 (8)	0.0035 (8)
C3	0.0651 (12)	0.0400 (10)	0.0374 (10)	−0.0168 (9)	0.0245 (9)	−0.0084 (8)
C4	0.0477 (10)	0.0448 (10)	0.0278 (8)	−0.0129 (8)	0.0143 (8)	−0.0043 (7)
C5	0.0448 (10)	0.0348 (9)	0.0278 (9)	−0.0085 (7)	0.0137 (7)	−0.0037 (7)
C6	0.0516 (11)	0.0410 (10)	0.0305 (9)	−0.0107 (8)	0.0126 (8)	−0.0011 (7)
C7	0.0355 (8)	0.0342 (9)	0.0315 (9)	0.0023 (7)	0.0152 (7)	0.0004 (7)
C8	0.0410 (9)	0.0347 (9)	0.0334 (9)	−0.0048 (7)	0.0181 (7)	−0.0038 (7)
C9	0.0492 (11)	0.0379 (10)	0.0447 (11)	0.0022 (8)	0.0224 (9)	0.0050 (8)
C10	0.0624 (13)	0.0402 (11)	0.0652 (14)	0.0035 (9)	0.0420 (11)	−0.0045 (9)
C11	0.0776 (14)	0.0523 (12)	0.0429 (11)	0.0011 (11)	0.0411 (11)	−0.0009 (9)
C12	0.0765 (15)	0.0617 (14)	0.0387 (11)	0.0184 (12)	0.0281 (11)	0.0106 (10)
C13	0.0594 (12)	0.0488 (11)	0.0398 (10)	0.0111 (9)	0.0271 (9)	0.0023 (8)
C14	0.0449 (9)	0.0345 (9)	0.0265 (8)	−0.0055 (7)	0.0161 (7)	0.0033 (7)
C15	0.0501 (11)	0.0404 (10)	0.0392 (10)	0.0029 (8)	0.0206 (8)	0.0048 (8)
C16	0.0821 (16)	0.0304 (10)	0.0503 (12)	−0.0004 (10)	0.0338 (11)	−0.0008 (8)
C17	0.0689 (14)	0.0413 (11)	0.0399 (10)	−0.0249 (10)	0.0207 (10)	−0.0024 (8)
C18	0.0448 (10)	0.0541 (12)	0.0472 (11)	−0.0080 (9)	0.0165 (9)	0.0082 (9)
C19	0.0500 (11)	0.0349 (10)	0.0442 (10)	0.0001 (8)	0.0232 (9)	0.0015 (8)

F1—C11	1.364 (2)	C7—C14	1.524 (2)
F2—C17	1.367 (2)	C7—C8	1.530 (2)
O1—C2	1.227 (2)	C7—H7	0.9800
N1—C2	1.349 (2)	C8—C13	1.372 (3)
N1—C3	1.458 (2)	C8—C9	1.381 (3)
N1—C6	1.465 (2)	C9—C10	1.396 (3)
N2—C4	1.462 (2)	C9—H9	0.9300
N2—C5	1.466 (2)	C10—C11	1.365 (3)
N2—C7	1.467 (2)	C10—H10	0.9300
C1—C2	1.505 (3)	C11—C12	1.368 (3)
C1—H1A	0.9600	C12—C13	1.386 (3)
C1—H1B	0.9600	C12—H12	0.9300
C1—H1C	0.9600	C13—H13	0.9300
C3—C4	1.505 (3)	C14—C15	1.378 (3)
C3—H3A	0.9700	C14—C19	1.393 (3)
C3—H3B	0.9700	C15—C16	1.379 (3)
C4—H4A	0.9700	C15—H15	0.9300
C4—H4B	0.9700	C16—C17	1.359 (3)
C5—C6	1.503 (3)	C16—H16	0.9300
C5—H5A	0.9700	C17—C18	1.365 (3)
C5—H5B	0.9700	C18—C19	1.383 (3)
C6—H6A	0.9700	C18—H18	0.9300
C6—H6B	0.9700	C19—H19	0.9300
C2—N1—C3	119.85 (15)	C14—C7—C8	109.55 (14)
C2—N1—C6	124.48 (15)	N2—C7—H7	108.2
C3—N1—C6	113.10 (15)	C14—C7—H7	108.2
C4—N2—C5	107.26 (13)	C8—C7—H7	108.2
C4—N2—C7	111.08 (13)	C13—C8—C9	119.04 (17)
C5—N2—C7	112.70 (13)	C13—C8—C7	118.44 (16)
C2—C1—H1A	109.5	C9—C8—C7	122.48 (16)
C2—C1—H1B	109.5	C8—C9—C10	120.84 (18)
H1A—C1—H1B	109.5	C8—C9—H9	119.6
C2—C1—H1C	109.5	C10—C9—H9	119.6
H1A—C1—H1C	109.5	C11—C10—C9	118.04 (18)
H1B—C1—H1C	109.5	C11—C10—H10	121.0
O1—C2—N1	121.36 (17)	C9—C10—H10	121.0
O1—C2—C1	121.08 (17)	F1—C11—C10	118.60 (19)
N1—C2—C1	117.55 (16)	F1—C11—C12	118.8 (2)
N1—C3—C4	110.18 (16)	C10—C11—C12	122.56 (19)
N1—C3—H3A	109.6	C11—C12—C13	118.4 (2)
C4—C3—H3A	109.6	C11—C12—H12	120.8
N1—C3—H3B	109.6	C13—C12—H12	120.8
C4—C3—H3B	109.6	C8—C13—C12	121.12 (19)
H3A—C3—H3B	108.1	C8—C13—H13	119.4
N2—C4—C3	111.16 (15)	C12—C13—H13	119.4
N2—C4—H4A	109.4	C15—C14—C19	118.84 (17)
C3—C4—H4A	109.4	C15—C14—C7	119.82 (17)
N2—C4—H4B	109.4	C19—C14—C7	121.33 (16)
C3—C4—H4B	109.4	C14—C15—C16	120.7 (2)
H4A—C4—H4B	108.0	C14—C15—H15	119.7
N2—C5—C6	111.14 (15)	C16—C15—H15	119.7
N2—C5—H5A	109.4	C17—C16—C15	118.8 (2)
C6—C5—H5A	109.4	C17—C16—H16	120.6
N2—C5—H5B	109.4	C15—C16—H16	120.6
C6—C5—H5B	109.4	C16—C17—C18	122.94 (19)
H5A—C5—H5B	108.0	C16—C17—F2	118.9 (2)
N1—C6—C5	111.02 (15)	C18—C17—F2	118.1 (2)
N1—C6—H6A	109.4	C17—C18—C19	118.0 (2)
C5—C6—H6A	109.4	C17—C18—H18	121.0
N1—C6—H6B	109.4	C19—C18—H18	121.0
C5—C6—H6B	109.4	C18—C19—C14	120.79 (19)
H6A—C6—H6B	108.0	C18—C19—H19	119.6
N2—C7—C14	111.23 (13)	C14—C19—H19	119.6
N2—C7—C8	111.40 (14)
C3—N1—C2—O1	−2.5 (3)	C7—C8—C9—C10	−178.25 (18)
C6—N1—C2—O1	−163.00 (19)	C8—C9—C10—C11	0.0 (3)
C3—N1—C2—C1	178.49 (18)	C9—C10—C11—F1	−179.4 (2)
C6—N1—C2—C1	17.9 (3)	C9—C10—C11—C12	0.8 (4)
C2—N1—C3—C4	145.48 (18)	F1—C11—C12—C13	179.4 (2)
C6—N1—C3—C4	−51.9 (2)	C10—C11—C12—C13	−0.8 (4)
C5—N2—C4—C3	−62.16 (19)	C9—C8—C13—C12	0.6 (3)
C7—N2—C4—C3	174.28 (15)	C7—C8—C13—C12	178.3 (2)
N1—C3—C4—N2	58.1 (2)	C11—C12—C13—C8	0.1 (4)
C4—N2—C5—C6	60.94 (19)	N2—C7—C14—C15	−124.60 (17)
C7—N2—C5—C6	−176.50 (14)	C8—C7—C14—C15	111.80 (18)
C2—N1—C6—C5	−147.07 (18)	N2—C7—C14—C19	55.1 (2)
C3—N1—C6—C5	51.2 (2)	C8—C7—C14—C19	−68.5 (2)
N2—C5—C6—N1	−56.0 (2)	C19—C14—C15—C16	−1.4 (3)
C4—N2—C7—C14	172.68 (14)	C7—C14—C15—C16	178.28 (17)
C5—N2—C7—C14	52.28 (18)	C14—C15—C16—C17	0.0 (3)
C4—N2—C7—C8	−64.78 (18)	C15—C16—C17—C18	1.3 (3)
C5—N2—C7—C8	174.82 (14)	C15—C16—C17—F2	−178.55 (18)
N2—C7—C8—C13	151.90 (17)	C16—C17—C18—C19	−1.1 (3)
C14—C7—C8—C13	−84.6 (2)	F2—C17—C18—C19	178.75 (18)
N2—C7—C8—C9	−30.5 (2)	C17—C18—C19—C14	−0.4 (3)
C14—C7—C8—C9	93.0 (2)	C15—C14—C19—C18	1.6 (3)
C13—C8—C9—C10	−0.7 (3)	C7—C14—C19—C18	−178.09 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1i	0.93	2.46	3.371 (2)	167
C15—H15···O1i	0.93	2.55	3.351 (3)	145
C18—H18···F2ii	0.93	2.54	3.319 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1i	0.93	2.46	3.371 (2)	167
C15—H15⋯O1i	0.93	2.55	3.351 (3)	145
C18—H18⋯F2ii	0.93	2.54	3.319 (3)	142

Symmetry codes: (i) ; (ii) .