2-(3,3,4,4-Tetra-fluoro-pyrrolidin-1-yl)aniline.

In the title fluorinated pyrrolidine derivative, C(10)H(10)F(4)N(2), the dihedral angle between the best planes of the benzene and pyrrolidine rings is 62.6 (1)°. The crystal packing features inter-molecular N-H⋯F hydrogen bonds.

Related literature

For applications of fluorinated pyrrolidine derivatives, see: Hulin et al. (2005 ▶); Kerekes et al. (2011 ▶); Marson (2005 ▶); Santora et al. (2008 ▶).

Experimental

Crystal data

C10H10F4N2

M = 234.20

Orthorhombic,

a = 6.791 (13) Å

b = 8.185 (16) Å

c = 18.66 (4) Å

V = 1037 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 298 K

0.30 × 0.28 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.959, T max = 0.970

6022 measured reflections

1342 independent reflections

748 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.112

S = 1.02

1342 reflections

153 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811030339/ld2018sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030339/ld2018Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811030339/ld2018Isup3.cml

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

C10H10F4N2	F(000) = 480
Mr = 234.20	Dx = 1.500 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
a = 6.791 (13) Å	µ = 0.14 mm−1
b = 8.185 (16) Å	T = 298 K
c = 18.66 (4) Å	Block, purple
V = 1037 (3) Å3	0.30 × 0.28 × 0.22 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	1342 independent reflections
Radiation source: fine-focus sealed tube	748 reflections with I > 2σ(I)
graphite	Rint = 0.061
φ and ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→7
Tmin = 0.959, Tmax = 0.970	k = −8→10
6022 measured reflections	l = −23→23

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.038P)2 + 0.0935P] where P = (Fo2 + 2Fc2)/3
1342 reflections	(Δ/σ)max < 0.001
153 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.15 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. Since this is a light atom structure (does not contain any atoms heavier than Si) and since the data collection was carried out using Mo radiation, it is not possible to unambiguously determine the absolute configuration of this molecule.

	x	y	z	Uiso*/Ueq
F2	0.5502 (4)	0.9533 (4)	0.28755 (12)	0.0946 (9)
F4	0.9856 (4)	0.9465 (4)	0.22927 (13)	0.0938 (9)
F3	0.7878 (4)	1.1542 (3)	0.23004 (13)	0.0903 (9)
F1	0.7058 (4)	0.7458 (3)	0.24699 (12)	0.0897 (8)
C5	0.5124 (5)	0.9963 (4)	0.04139 (17)	0.0451 (8)
C6	0.3393 (5)	1.0854 (4)	0.02680 (18)	0.0491 (9)
C3	0.8125 (6)	1.0019 (5)	0.2037 (2)	0.0608 (10)
C2	0.6375 (6)	0.8962 (5)	0.22754 (19)	0.0595 (11)
C10	0.6062 (6)	0.9131 (5)	−0.01323 (19)	0.0575 (10)
H10	0.7199	0.8541	−0.0031	0.069*
C7	0.2663 (6)	1.0832 (5)	−0.0431 (2)	0.0605 (11)
H7	0.1501	1.1383	−0.0536	0.073*
C8	0.3635 (7)	1.0009 (5)	−0.0966 (2)	0.0688 (12)
H8	0.3133	1.0027	−0.1430	0.083*
C9	0.5346 (7)	0.9155 (5)	−0.0827 (2)	0.0716 (13)
H9	0.6004	0.8608	−0.1192	0.086*
C4	0.7993 (5)	0.9997 (5)	0.12353 (18)	0.0583 (10)
H4A	0.8623	1.0946	0.1025	0.070*
H4B	0.8569	0.9013	0.1036	0.070*
C1	0.5016 (6)	0.8845 (5)	0.16406 (19)	0.0665 (12)
H1A	0.5021	0.7752	0.1440	0.080*
H1B	0.3679	0.9136	0.1771	0.080*
N1	0.5854 (4)	1.0035 (4)	0.11341 (14)	0.0466 (7)
N2	0.2447 (6)	1.1710 (5)	0.0805 (2)	0.0653 (10)
H2A	0.312 (7)	1.201 (6)	0.116 (3)	0.091 (19)*
H2B	0.171 (9)	1.254 (9)	0.068 (3)	0.17 (3)*

	U11	U22	U33	U12	U13	U23
F2	0.093 (2)	0.123 (2)	0.0670 (14)	0.0049 (17)	0.0166 (15)	−0.0149 (14)
F4	0.0610 (15)	0.127 (2)	0.0934 (19)	0.0073 (16)	−0.0274 (15)	0.0235 (16)
F3	0.118 (2)	0.0611 (15)	0.0915 (17)	−0.0124 (16)	−0.0215 (16)	−0.0148 (13)
F1	0.111 (2)	0.0665 (15)	0.0915 (17)	0.0003 (16)	−0.0187 (16)	0.0234 (14)
C5	0.041 (2)	0.047 (2)	0.0470 (18)	−0.0033 (19)	−0.0009 (17)	0.0050 (16)
C6	0.047 (2)	0.046 (2)	0.054 (2)	−0.0019 (18)	−0.0030 (19)	0.0006 (18)
C3	0.056 (3)	0.058 (3)	0.068 (2)	0.007 (2)	−0.016 (2)	0.004 (2)
C2	0.069 (3)	0.062 (3)	0.048 (2)	0.006 (2)	−0.002 (2)	0.008 (2)
C10	0.058 (2)	0.055 (2)	0.059 (2)	0.004 (2)	0.003 (2)	−0.0032 (19)
C7	0.057 (3)	0.061 (2)	0.064 (2)	0.000 (2)	−0.016 (2)	0.009 (2)
C8	0.090 (3)	0.069 (3)	0.047 (2)	−0.013 (3)	−0.013 (2)	0.000 (2)
C9	0.087 (4)	0.069 (3)	0.058 (3)	−0.005 (3)	0.005 (2)	−0.011 (2)
C4	0.044 (2)	0.070 (3)	0.061 (2)	−0.004 (2)	−0.0026 (19)	0.010 (2)
C1	0.064 (3)	0.074 (3)	0.061 (2)	−0.017 (2)	−0.005 (2)	0.017 (2)
N1	0.0369 (16)	0.0548 (18)	0.0480 (16)	−0.0026 (15)	−0.0024 (14)	0.0073 (15)
N2	0.052 (2)	0.073 (2)	0.071 (2)	0.011 (2)	0.001 (2)	−0.004 (2)

F2—C2	1.350 (5)	C7—C8	1.374 (6)
F4—C3	1.347 (5)	C7—H7	0.9300
F3—C3	1.350 (5)	C8—C9	1.380 (6)
F1—C2	1.365 (5)	C8—H8	0.9300
C5—C10	1.382 (5)	C9—H9	0.9300
C5—C6	1.409 (5)	C4—N1	1.465 (5)
C5—N1	1.434 (5)	C4—H4A	0.9700
C6—N2	1.381 (5)	C4—H4B	0.9700
C6—C7	1.395 (5)	C1—N1	1.472 (5)
C3—C4	1.498 (6)	C1—H1A	0.9700
C3—C2	1.536 (6)	C1—H1B	0.9700
C2—C1	1.505 (6)	N2—H2A	0.84 (5)
C10—C9	1.384 (6)	N2—H2B	0.87 (7)
C10—H10	0.9300
C10—C5—C6	119.8 (3)	C7—C8—C9	121.1 (4)
C10—C5—N1	123.5 (3)	C7—C8—H8	119.5
C6—C5—N1	116.6 (3)	C9—C8—H8	119.5
N2—C6—C7	121.3 (4)	C8—C9—C10	118.6 (4)
N2—C6—C5	120.7 (3)	C8—C9—H9	120.7
C7—C6—C5	118.1 (3)	C10—C9—H9	120.7
F4—C3—F3	106.8 (3)	N1—C4—C3	100.8 (3)
F4—C3—C4	113.7 (3)	N1—C4—H4A	111.6
F3—C3—C4	111.6 (3)	C3—C4—H4A	111.6
F4—C3—C2	112.5 (3)	N1—C4—H4B	111.6
F3—C3—C2	108.6 (3)	C3—C4—H4B	111.6
C4—C3—C2	103.7 (3)	H4A—C4—H4B	109.4
F2—C2—F1	103.9 (3)	N1—C1—C2	103.1 (3)
F2—C2—C1	113.9 (4)	N1—C1—H1A	111.2
F1—C2—C1	111.1 (3)	C2—C1—H1A	111.2
F2—C2—C3	112.7 (4)	N1—C1—H1B	111.2
F1—C2—C3	108.8 (3)	C2—C1—H1B	111.2
C1—C2—C3	106.4 (3)	H1A—C1—H1B	109.1
C5—C10—C9	121.5 (4)	C5—N1—C4	117.6 (3)
C5—C10—H10	119.3	C5—N1—C1	116.2 (3)
C9—C10—H10	119.3	C4—N1—C1	106.7 (3)
C8—C7—C6	121.0 (4)	C6—N2—H2A	117 (3)
C8—C7—H7	119.5	C6—N2—H2B	118 (4)
C6—C7—H7	119.5	H2A—N2—H2B	107 (5)
C10—C5—C6—N2	−179.2 (4)	C6—C7—C8—C9	1.1 (6)
N1—C5—C6—N2	−1.6 (5)	C7—C8—C9—C10	0.6 (6)
C10—C5—C6—C7	1.3 (5)	C5—C10—C9—C8	−1.3 (6)
N1—C5—C6—C7	178.9 (3)	F4—C3—C4—N1	159.5 (3)
F4—C3—C2—F2	93.9 (4)	F3—C3—C4—N1	−79.6 (4)
F3—C3—C2—F2	−24.1 (4)	C2—C3—C4—N1	37.0 (4)
C4—C3—C2—F2	−142.8 (3)	F2—C2—C1—N1	115.4 (4)
F4—C3—C2—F1	−20.8 (4)	F1—C2—C1—N1	−127.7 (4)
F3—C3—C2—F1	−138.8 (3)	C3—C2—C1—N1	−9.4 (4)
C4—C3—C2—F1	102.5 (3)	C10—C5—N1—C4	31.8 (5)
F4—C3—C2—C1	−140.6 (4)	C6—C5—N1—C4	−145.8 (4)
F3—C3—C2—C1	101.4 (4)	C10—C5—N1—C1	−96.3 (4)
C4—C3—C2—C1	−17.3 (4)	C6—C5—N1—C1	86.2 (4)
C6—C5—C10—C9	0.3 (5)	C3—C4—N1—C5	−177.7 (3)
N1—C5—C10—C9	−177.1 (4)	C3—C4—N1—C1	−45.2 (4)
N2—C6—C7—C8	178.5 (4)	C2—C1—N1—C5	167.3 (3)
C5—C6—C7—C8	−2.0 (6)	C2—C1—N1—C4	34.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···F1i	0.84 (5)	2.59 (5)	3.295 (8)	142 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯F1i	0.84 (5)	2.59 (5)	3.295 (8)	142 (4)

Symmetry code: (i) .