1-[Bis(4-fluoro-phen-yl)meth-yl]piperazine.

In the title mol-ecule, C(17)H(18)F(2)N(2), the dihedral angle between the benzene rings is 73.40 (3)°. The piperazine ring is close to an ideal chair conformation and the N-H hydrogen is in an equatorial position. In the crystal, molecules are linked via weak C-H⋯F hydrogen bonds.

Related literature

For medical applications of piperazines, see: Bogatcheva et al. (2006 ▶); Brockunier et al. (2004 ▶). For related structures, see: Betz et al. (2011a ▶,b ▶); Hu et al. (2003 ▶); Naveen et al. (2006 ▶). For asymmetry parameters, see: Duax & Norton (1975 ▶).

Experimental

Crystal data

C17H18F2N2

M = 288.33

Monoclinic,

a = 12.1574 (5) Å

b = 8.8559 (2) Å

c = 13.8604 (4) Å

β = 93.355 (3)°

V = 1489.72 (8) Å3

Z = 4

Cu Kα radiation

μ = 0.77 mm−1

T = 130 K

0.15 × 0.08 × 0.06 mm

Data collection

Atlas SuperNova (Single source at offset) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.828, T max = 1.000

8816 measured reflections

3006 independent reflections

2847 reflections with I > 2σ(I)

R int = 0.010

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.096

S = 1.04

3006 reflections

262 parameters

All H-atom parameters refined

Δρmax = 0.18 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812036902/mw2085sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036902/mw2085Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812036902/mw2085Isup3.cml

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

C17H18F2N2	F(000) = 608
Mr = 288.33	Dx = 1.286 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 110 reflections
a = 12.1574 (5) Å	θ = 2.9–27.8°
b = 8.8559 (2) Å	µ = 0.77 mm−1
c = 13.8604 (4) Å	T = 130 K
β = 93.355 (3)°	Block, colourless
V = 1489.72 (8) Å3	0.15 × 0.08 × 0.06 mm
Z = 4

Atlas SuperNova (Single source at offset) diffractometer	3006 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2847 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.010
Detector resolution: 10.5357 pixels mm-1	θmax = 75.3°, θmin = 3.6°
ω scan	h = −15→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −9→10
Tmin = 0.828, Tmax = 1.000	l = −14→17
8816 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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F2) = 0.096	All H-atom parameters refined
S = 1.04	w = 1/[σ2(Fo2) + (0.0518P)2 + 0.3446P] where P = (Fo2 + 2Fc2)/3
3006 reflections	(Δ/σ)max = 0.001
262 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.71855 (8)	0.26307 (12)	0.64093 (7)	0.0297 (2)
H1	0.6808 (10)	0.1909 (14)	0.5950 (9)	0.031 (3)*
N11	0.82339 (7)	0.19519 (10)	0.67957 (6)	0.0296 (2)
C12	0.89231 (9)	0.15265 (14)	0.59996 (9)	0.0377 (3)
H12B	0.9123 (11)	0.2450 (16)	0.5634 (10)	0.040 (3)*
H12A	0.8512 (12)	0.0821 (16)	0.5550 (10)	0.044 (4)*
C13	0.99715 (9)	0.07353 (14)	0.63834 (9)	0.0388 (3)
H13B	1.0416 (12)	0.0469 (16)	0.5818 (11)	0.048 (4)*
H13A	1.0429 (11)	0.1472 (16)	0.6811 (10)	0.041 (3)*
N14	0.96894 (8)	−0.06217 (11)	0.69096 (8)	0.0400 (2)
H14	1.0301 (12)	−0.1145 (17)	0.7121 (10)	0.047 (4)*
C15	0.90455 (10)	−0.01932 (14)	0.77224 (10)	0.0428 (3)
H15B	0.9468 (12)	0.0538 (18)	0.8199 (10)	0.050 (4)*
H15A	0.8848 (12)	−0.1141 (18)	0.8085 (11)	0.054 (4)*
C16	0.79931 (9)	0.05778 (13)	0.73443 (10)	0.0388 (3)
H16B	0.7563 (12)	−0.0116 (17)	0.6926 (10)	0.046 (4)*
H16A	0.7553 (11)	0.0865 (16)	0.7897 (10)	0.043 (4)*
C21	0.64243 (8)	0.29345 (11)	0.72207 (7)	0.0282 (2)
C22	0.53738 (9)	0.23052 (12)	0.71842 (9)	0.0343 (2)
H22	0.5114 (11)	0.1663 (16)	0.6633 (10)	0.040 (3)*
C23	0.46608 (9)	0.25595 (13)	0.79170 (9)	0.0379 (3)
H23	0.3926 (13)	0.2108 (17)	0.7896 (11)	0.051 (4)*
C24	0.50228 (9)	0.34553 (12)	0.86750 (8)	0.0344 (2)
F24	0.43371 (6)	0.37247 (9)	0.93966 (5)	0.0496 (2)
C25	0.60588 (9)	0.41045 (12)	0.87452 (8)	0.0324 (2)
H25	0.6270 (11)	0.4725 (16)	0.9295 (10)	0.038 (3)*
C26	0.67547 (8)	0.38383 (12)	0.80075 (8)	0.0299 (2)
H26	0.7491 (12)	0.4266 (15)	0.8047 (10)	0.042 (3)*
C31	0.73448 (8)	0.40781 (12)	0.58434 (7)	0.0301 (2)
C32	0.81328 (9)	0.51586 (13)	0.61203 (8)	0.0369 (3)
H32	0.8644 (12)	0.4954 (16)	0.6675 (10)	0.045 (4)*
C33	0.82205 (10)	0.65060 (14)	0.56149 (9)	0.0418 (3)
H33	0.8754 (13)	0.7275 (19)	0.5793 (11)	0.056 (4)*
C34	0.75027 (10)	0.67407 (13)	0.48296 (9)	0.0401 (3)
F34	0.75839 (7)	0.80528 (9)	0.43211 (6)	0.0570 (2)
C35	0.66997 (10)	0.57242 (15)	0.45345 (8)	0.0426 (3)
H35	0.6225 (13)	0.5946 (19)	0.3972 (12)	0.057 (4)*
C36	0.66273 (9)	0.43910 (14)	0.50508 (8)	0.0370 (3)
H36	0.6086 (12)	0.3684 (17)	0.4860 (10)	0.045 (4)*

	U11	U22	U33	U12	U13	U23
C1	0.0265 (5)	0.0272 (5)	0.0352 (5)	−0.0020 (4)	−0.0011 (4)	−0.0051 (4)
N11	0.0259 (4)	0.0261 (4)	0.0369 (5)	0.0014 (3)	0.0034 (3)	−0.0010 (3)
C12	0.0340 (5)	0.0403 (6)	0.0393 (6)	0.0027 (5)	0.0062 (4)	−0.0066 (5)
C13	0.0296 (5)	0.0384 (6)	0.0490 (7)	0.0004 (4)	0.0071 (5)	−0.0099 (5)
N14	0.0278 (5)	0.0288 (5)	0.0634 (6)	0.0031 (4)	0.0023 (4)	−0.0078 (4)
C15	0.0353 (6)	0.0338 (6)	0.0600 (7)	0.0080 (5)	0.0096 (5)	0.0089 (5)
C16	0.0298 (5)	0.0283 (5)	0.0591 (7)	0.0025 (4)	0.0092 (5)	0.0061 (5)
C21	0.0259 (5)	0.0220 (5)	0.0363 (5)	0.0016 (4)	−0.0006 (4)	0.0011 (4)
C22	0.0284 (5)	0.0273 (5)	0.0470 (6)	−0.0023 (4)	−0.0004 (4)	−0.0037 (4)
C23	0.0270 (5)	0.0311 (6)	0.0559 (7)	−0.0020 (4)	0.0051 (5)	0.0017 (5)
C24	0.0328 (5)	0.0287 (5)	0.0426 (6)	0.0060 (4)	0.0104 (4)	0.0056 (4)
F24	0.0458 (4)	0.0492 (4)	0.0562 (4)	0.0006 (3)	0.0237 (3)	−0.0013 (3)
C25	0.0343 (5)	0.0272 (5)	0.0357 (5)	0.0030 (4)	0.0007 (4)	0.0009 (4)
C26	0.0258 (5)	0.0267 (5)	0.0370 (5)	−0.0006 (4)	−0.0008 (4)	0.0010 (4)
C31	0.0291 (5)	0.0300 (5)	0.0312 (5)	0.0015 (4)	0.0028 (4)	−0.0034 (4)
C32	0.0333 (5)	0.0375 (6)	0.0393 (6)	−0.0047 (4)	−0.0035 (4)	0.0048 (5)
C33	0.0365 (6)	0.0373 (6)	0.0518 (7)	−0.0054 (5)	0.0045 (5)	0.0058 (5)
C34	0.0426 (6)	0.0368 (6)	0.0423 (6)	0.0095 (5)	0.0138 (5)	0.0110 (5)
F34	0.0578 (5)	0.0500 (5)	0.0649 (5)	0.0125 (4)	0.0191 (4)	0.0278 (4)
C35	0.0457 (6)	0.0478 (7)	0.0339 (6)	0.0133 (5)	−0.0014 (5)	0.0017 (5)
C36	0.0370 (6)	0.0373 (6)	0.0359 (5)	0.0028 (5)	−0.0041 (4)	−0.0074 (5)

C1—N11	1.4808 (13)	C22—C23	1.3917 (16)
C1—C31	1.5211 (15)	C22—H22	0.989 (14)
C1—C21	1.5216 (14)	C23—C24	1.3684 (17)
C1—H1	0.996 (12)	C23—H23	0.978 (16)
N11—C12	1.4729 (14)	C24—F24	1.3601 (12)
N11—C16	1.4734 (14)	C24—C25	1.3828 (16)
C12—C13	1.5229 (16)	C25—C26	1.3849 (15)
C12—H12B	0.999 (14)	C25—H25	0.962 (14)
C12—H12A	0.996 (15)	C26—H26	0.970 (14)
C13—N14	1.4571 (16)	C31—C36	1.3901 (15)
C13—H13B	1.006 (15)	C31—C32	1.3920 (15)
C13—H13A	1.023 (14)	C32—C33	1.3909 (16)
N14—C15	1.4592 (16)	C32—H32	0.976 (14)
N14—H14	0.909 (15)	C33—C34	1.3706 (17)
C15—C16	1.5164 (16)	C33—H33	0.962 (17)
C15—H15B	1.039 (15)	C34—F34	1.3656 (13)
C15—H15A	1.015 (16)	C34—C35	1.3725 (19)
C16—H16B	0.976 (15)	C35—C36	1.3861 (18)
C16—H16A	0.993 (14)	C35—H35	0.963 (16)
C21—C22	1.3917 (14)	C36—H36	0.935 (15)
C21—C26	1.3928 (15)
N11—C1—C31	113.31 (8)	C22—C21—C26	118.72 (10)
N11—C1—C21	110.63 (8)	C22—C21—C1	119.93 (9)
C31—C1—C21	109.48 (8)	C26—C21—C1	121.35 (9)
N11—C1—H1	109.0 (7)	C21—C22—C23	121.21 (10)
C31—C1—H1	106.2 (7)	C21—C22—H22	120.6 (8)
C21—C1—H1	108.0 (7)	C23—C22—H22	118.2 (8)
C12—N11—C16	108.32 (9)	C24—C23—C22	117.91 (10)
C12—N11—C1	110.38 (8)	C24—C23—H23	120.8 (9)
C16—N11—C1	109.22 (8)	C22—C23—H23	121.3 (9)
N11—C12—C13	110.93 (9)	F24—C24—C23	118.87 (10)
N11—C12—H12B	109.7 (8)	F24—C24—C25	118.05 (10)
C13—C12—H12B	109.3 (8)	C23—C24—C25	123.08 (10)
N11—C12—H12A	110.1 (8)	C24—C25—C26	118.07 (10)
C13—C12—H12A	108.0 (8)	C24—C25—H25	119.6 (8)
H12B—C12—H12A	108.9 (11)	C26—C25—H25	122.4 (8)
N14—C13—C12	109.73 (9)	C25—C26—C21	121.01 (9)
N14—C13—H13B	110.5 (8)	C25—C26—H26	119.6 (8)
C12—C13—H13B	108.2 (8)	C21—C26—H26	119.4 (8)
N14—C13—H13A	111.8 (8)	C36—C31—C32	118.08 (10)
C12—C13—H13A	108.9 (8)	C36—C31—C1	118.86 (9)
H13B—C13—H13A	107.6 (11)	C32—C31—C1	122.92 (9)
C13—N14—C15	108.94 (9)	C33—C32—C31	121.51 (10)
C13—N14—H14	111.7 (9)	C33—C32—H32	119.5 (9)
C15—N14—H14	110.4 (9)	C31—C32—H32	119.0 (9)
N14—C15—C16	109.28 (11)	C34—C33—C32	117.78 (11)
N14—C15—H15B	112.6 (8)	C34—C33—H33	119.0 (9)
C16—C15—H15B	108.4 (8)	C32—C33—H33	123.2 (9)
N14—C15—H15A	108.7 (9)	F34—C34—C33	118.49 (11)
C16—C15—H15A	108.9 (9)	F34—C34—C35	118.42 (11)
H15B—C15—H15A	108.8 (12)	C33—C34—C35	123.09 (11)
N11—C16—C15	111.17 (9)	C34—C35—C36	118.06 (11)
N11—C16—H16B	109.2 (9)	C34—C35—H35	119.3 (10)
C15—C16—H16B	109.5 (9)	C36—C35—H35	122.6 (10)
N11—C16—H16A	108.6 (8)	C35—C36—C31	121.46 (11)
C15—C16—H16A	109.3 (8)	C35—C36—H36	119.3 (9)
H16B—C16—H16A	109.0 (11)	C31—C36—H36	119.3 (9)
C31—C1—N11—C12	−62.03 (11)	C22—C23—C24—C25	−0.37 (17)
C21—C1—N11—C12	174.59 (8)	F24—C24—C25—C26	−179.60 (9)
C31—C1—N11—C16	178.99 (9)	C23—C24—C25—C26	0.45 (16)
C21—C1—N11—C16	55.61 (11)	C24—C25—C26—C21	−0.44 (15)
C16—N11—C12—C13	−56.84 (12)	C22—C21—C26—C25	0.36 (15)
C1—N11—C12—C13	−176.37 (9)	C1—C21—C26—C25	−179.73 (9)
N11—C12—C13—N14	59.56 (12)	N11—C1—C31—C36	145.48 (10)
C12—C13—N14—C15	−60.72 (12)	C21—C1—C31—C36	−90.50 (11)
C13—N14—C15—C16	60.98 (12)	N11—C1—C31—C32	−38.94 (14)
C12—N11—C16—C15	57.53 (13)	C21—C1—C31—C32	85.07 (12)
C1—N11—C16—C15	177.79 (10)	C36—C31—C32—C33	−1.06 (17)
N14—C15—C16—N11	−60.40 (13)	C1—C31—C32—C33	−176.67 (10)
N11—C1—C21—C22	−123.14 (10)	C31—C32—C33—C34	−0.02 (18)
C31—C1—C21—C22	111.29 (10)	C32—C33—C34—F34	−179.48 (10)
N11—C1—C21—C26	56.95 (12)	C32—C33—C34—C35	1.07 (19)
C31—C1—C21—C26	−68.62 (12)	F34—C34—C35—C36	179.60 (10)
C26—C21—C22—C23	−0.28 (16)	C33—C34—C35—C36	−0.95 (18)
C1—C21—C22—C23	179.81 (10)	C34—C35—C36—C31	−0.22 (17)
C21—C22—C23—C24	0.28 (17)	C32—C31—C36—C35	1.19 (17)
C22—C23—C24—F24	179.68 (10)	C1—C31—C36—C35	176.98 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25···F24i	0.962 (14)	2.424 (14)	3.2720 (13)	146.8 (10)
C25—H25···F34ii	0.962 (14)	2.533 (14)	3.1998 (13)	126.5 (10)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C25—H25⋯F24i	0.962 (14)	2.424 (14)	3.2720 (13)	146.8 (10)
C25—H25⋯F34ii	0.962 (14)	2.533 (14)	3.1998 (13)	126.5 (10)

Symmetry codes: (i) ; (ii) .