r-2,c-6-Bis(4-fluoro-phen-yl)-t-3,t-5-dimethyl-piperidin-4-one.

In the title compound, C(19)H(19)F(2)NO, the piperidinone ring adopts a chair conformation. The crystal packing is stabilized by C-H⋯O and C-H⋯F inter-molecular inter-actions, generating centrosymmetric dimers of R(2) (2)(14) and R(2) (2)(24) rings.

Related literature

For related literature, see: Allen et al. (1987 ▶); Cremer & Pople (1975 ▶); Ganellin & Spickett (1965 ▶); Nardelli (1983 ▶); Noller & Baliah (1948 ▶).

Experimental

Crystal data

C19H19F2NO

M = 315.35

Monoclinic,

a = 7.3830 (6) Å

b = 24.0102 (19) Å

c = 9.4278 (7) Å

β = 101.727 (1)°

V = 1636.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.27 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: none

18490 measured reflections

3851 independent reflections

2773 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.212

S = 1.04

3851 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.43 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: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068699/at2525sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068699/at2525Isup2.hkl

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

C19H19F2NO	F000 = 664
Mr = 315.35	Dx = 1.280 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2923 reflections
a = 7.3830 (6) Å	θ = 2.4–28.1º
b = 24.0102 (19) Å	µ = 0.09 mm−1
c = 9.4278 (7) Å	T = 293 (2) K
β = 101.7270 (10)º	Block, colourless
V = 1636.4 (2) Å3	0.27 × 0.24 × 0.22 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2773 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Monochromator: graphite	θmax = 28.1º
T = 293(2) K	θmin = 2.4º
ω scans	h = −9→9
Absorption correction: none	k = −31→31
18490 measured reflections	l = −12→12
3851 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061	H-atom parameters constrained
wR(F2) = 0.212	w = 1/[σ2(Fo2) + (0.1249P)2 + 0.205P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3851 reflections	Δρmax = 0.52 e Å−3
210 parameters	Δρmin = −0.43 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
C1	0.6972 (2)	0.02549 (6)	0.79954 (16)	0.0546 (4)
H1	0.7019	0.0285	0.9039	0.066*
C2	0.4928 (2)	0.01783 (7)	0.72123 (19)	0.0624 (4)
H2	0.4918	0.0147	0.6174	0.075*
C3	0.3828 (2)	0.06935 (7)	0.74162 (19)	0.0637 (4)
C4	0.4655 (2)	0.12406 (7)	0.7076 (2)	0.0637 (4)
H4	0.4654	0.1244	0.6036	0.076*
C5	0.6706 (2)	0.12620 (6)	0.78990 (18)	0.0585 (4)
H5	0.6736	0.1247	0.8942	0.070*
C6	0.8102 (2)	−0.02404 (6)	0.77288 (17)	0.0558 (4)
C7	0.8517 (2)	−0.03400 (7)	0.63869 (18)	0.0617 (4)
H7	0.8203	−0.0075	0.5658	0.074*
C8	0.9388 (3)	−0.08247 (8)	0.6106 (2)	0.0734 (5)
H8	0.9653	−0.0891	0.5197	0.088*
C9	0.9851 (3)	−0.12059 (8)	0.7203 (3)	0.0784 (6)
C10	0.9494 (3)	−0.11202 (8)	0.8545 (3)	0.0834 (6)
H10	0.9829	−0.1385	0.9270	0.100*
C11	0.8626 (3)	−0.06341 (8)	0.8813 (2)	0.0701 (5)
H11	0.8389	−0.0569	0.9731	0.084*
C12	0.4069 (3)	−0.03515 (10)	0.7657 (3)	0.0970 (7)
H12A	0.4217	−0.0361	0.8692	0.145*
H12B	0.4671	−0.0669	0.7339	0.145*
H12C	0.2776	−0.0360	0.7220	0.145*
C13	0.3516 (3)	0.17334 (10)	0.7391 (3)	0.1006 (8)
H13A	0.2274	0.1698	0.6843	0.151*
H13B	0.4054	0.2072	0.7124	0.151*
H13C	0.3498	0.1742	0.8406	0.151*
C14	0.7637 (2)	0.17899 (7)	0.75681 (19)	0.0638 (4)
C15	0.8070 (3)	0.22048 (8)	0.8600 (3)	0.0826 (6)
H15	0.7817	0.2156	0.9519	0.099*
C16	0.8895 (4)	0.27015 (9)	0.8253 (4)	0.1013 (8)
H16	0.9191	0.2984	0.8936	0.122*
C17	0.9248 (3)	0.27607 (8)	0.6917 (4)	0.0966 (8)
C18	0.8849 (3)	0.23645 (8)	0.5878 (3)	0.0898 (6)
H18	0.9113	0.2419	0.4965	0.108*
C19	0.8036 (3)	0.18753 (7)	0.6218 (2)	0.0720 (5)
H19	0.7752	0.1598	0.5519	0.086*
N1	0.76605 (17)	0.07730 (5)	0.74933 (14)	0.0547 (3)
H1A	0.8532	0.0789	0.7012	0.066*
O1	0.23876 (19)	0.06688 (7)	0.78279 (19)	0.0912 (5)
F1	1.0695 (2)	−0.16840 (5)	0.6943 (2)	0.1173 (5)
F2	1.0055 (3)	0.32416 (6)	0.6583 (3)	0.1454 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0543 (8)	0.0562 (8)	0.0523 (8)	−0.0027 (6)	0.0080 (6)	−0.0002 (6)
C2	0.0525 (8)	0.0638 (10)	0.0695 (10)	−0.0072 (7)	0.0093 (7)	−0.0038 (7)
C3	0.0502 (8)	0.0763 (11)	0.0633 (9)	−0.0018 (7)	0.0084 (7)	−0.0059 (7)
C4	0.0509 (8)	0.0639 (10)	0.0743 (10)	0.0065 (7)	0.0079 (7)	−0.0064 (7)
C5	0.0544 (8)	0.0582 (9)	0.0605 (9)	0.0025 (6)	0.0060 (7)	−0.0076 (6)
C6	0.0510 (8)	0.0525 (8)	0.0605 (8)	−0.0040 (6)	0.0032 (6)	0.0024 (6)
C7	0.0579 (9)	0.0612 (9)	0.0634 (9)	0.0009 (7)	0.0062 (7)	0.0013 (7)
C8	0.0653 (10)	0.0724 (11)	0.0813 (12)	0.0021 (8)	0.0118 (9)	−0.0131 (9)
C9	0.0643 (11)	0.0548 (10)	0.1119 (16)	0.0029 (7)	0.0080 (10)	−0.0088 (9)
C10	0.0781 (12)	0.0635 (10)	0.1024 (15)	0.0059 (9)	0.0038 (11)	0.0227 (10)
C11	0.0735 (11)	0.0676 (10)	0.0659 (10)	0.0017 (8)	0.0068 (8)	0.0106 (8)
C12	0.0677 (12)	0.0771 (13)	0.146 (2)	−0.0166 (10)	0.0219 (13)	0.0080 (13)
C13	0.0664 (12)	0.0806 (14)	0.152 (2)	0.0176 (10)	0.0151 (12)	−0.0246 (14)
C14	0.0507 (8)	0.0528 (9)	0.0826 (11)	0.0072 (6)	0.0011 (7)	−0.0059 (7)
C15	0.0809 (13)	0.0637 (11)	0.0947 (13)	0.0047 (9)	−0.0027 (10)	−0.0171 (9)
C16	0.0944 (16)	0.0576 (11)	0.137 (2)	−0.0005 (10)	−0.0127 (15)	−0.0248 (13)
C17	0.0759 (13)	0.0525 (11)	0.155 (2)	−0.0002 (9)	0.0075 (14)	0.0060 (12)
C18	0.0858 (14)	0.0607 (11)	0.1247 (18)	0.0027 (9)	0.0259 (13)	0.0133 (11)
C19	0.0701 (10)	0.0563 (9)	0.0901 (13)	0.0003 (8)	0.0172 (9)	−0.0003 (8)
N1	0.0475 (6)	0.0518 (7)	0.0642 (8)	0.0015 (5)	0.0101 (5)	−0.0008 (5)
O1	0.0608 (8)	0.1076 (11)	0.1127 (12)	0.0004 (7)	0.0352 (8)	−0.0006 (8)
F1	0.1099 (11)	0.0692 (8)	0.1703 (15)	0.0267 (7)	0.0223 (10)	−0.0127 (8)
F2	0.1327 (14)	0.0643 (8)	0.236 (2)	−0.0278 (8)	0.0287 (13)	0.0108 (10)

C1—N1	1.4588 (19)	C9—C10	1.359 (3)
C1—C6	1.503 (2)	C10—C11	1.379 (3)
C1—C2	1.550 (2)	C10—H10	0.9300
C1—H1	0.9800	C11—H11	0.9300
C2—C3	1.513 (2)	C12—H12A	0.9600
C2—C12	1.518 (3)	C12—H12B	0.9600
C2—H2	0.9800	C12—H12C	0.9600
C3—O1	1.206 (2)	C13—H13A	0.9600
C3—C4	1.510 (2)	C13—H13B	0.9600
C4—C13	1.516 (2)	C13—H13C	0.9600
C4—C5	1.556 (2)	C14—C19	1.379 (3)
C4—H4	0.9800	C14—C15	1.384 (3)
C5—N1	1.4595 (19)	C15—C16	1.408 (3)
C5—C14	1.504 (2)	C15—H15	0.9300
C5—H5	0.9800	C16—C17	1.345 (4)
C6—C7	1.382 (2)	C16—H16	0.9300
C6—C11	1.388 (2)	C17—C18	1.354 (4)
C7—C8	1.381 (2)	C17—F2	1.365 (3)
C7—H7	0.9300	C18—C19	1.386 (3)
C8—C9	1.371 (3)	C18—H18	0.9300
C8—H8	0.9300	C19—H19	0.9300
C9—F1	1.352 (2)	N1—H1A	0.8600
N1—C1—C6	112.25 (12)	C9—C10—C11	118.93 (18)
N1—C1—C2	108.44 (12)	C9—C10—H10	120.5
C6—C1—C2	110.25 (12)	C11—C10—H10	120.5
N1—C1—H1	108.6	C10—C11—C6	120.77 (18)
C6—C1—H1	108.6	C10—C11—H11	119.6
C2—C1—H1	108.6	C6—C11—H11	119.6
C3—C2—C12	112.65 (15)	C2—C12—H12A	109.5
C3—C2—C1	109.75 (13)	C2—C12—H12B	109.5
C12—C2—C1	112.88 (15)	H12A—C12—H12B	109.5
C3—C2—H2	107.1	C2—C12—H12C	109.5
C12—C2—H2	107.1	H12A—C12—H12C	109.5
C1—C2—H2	107.1	H12B—C12—H12C	109.5
O1—C3—C4	122.16 (16)	C4—C13—H13A	109.5
O1—C3—C2	122.14 (16)	C4—C13—H13B	109.5
C4—C3—C2	115.70 (13)	H13A—C13—H13B	109.5
C3—C4—C13	111.89 (16)	C4—C13—H13C	109.5
C3—C4—C5	108.50 (13)	H13A—C13—H13C	109.5
C13—C4—C5	113.54 (15)	H13B—C13—H13C	109.5
C3—C4—H4	107.6	C19—C14—C15	118.66 (18)
C13—C4—H4	107.6	C19—C14—C5	120.60 (15)
C5—C4—H4	107.6	C15—C14—C5	120.73 (18)
N1—C5—C14	111.00 (13)	C14—C15—C16	119.7 (2)
N1—C5—C4	108.39 (12)	C14—C15—H15	120.1
C14—C5—C4	111.32 (13)	C16—C15—H15	120.1
N1—C5—H5	108.7	C17—C16—C15	118.8 (2)
C14—C5—H5	108.7	C17—C16—H16	120.6
C4—C5—H5	108.7	C15—C16—H16	120.6
C7—C6—C11	118.41 (16)	C16—C17—C18	123.2 (2)
C7—C6—C1	121.60 (14)	C16—C17—F2	118.8 (2)
C11—C6—C1	119.79 (15)	C18—C17—F2	118.0 (3)
C8—C7—C6	121.34 (16)	C17—C18—C19	118.0 (2)
C8—C7—H7	119.3	C17—C18—H18	121.0
C6—C7—H7	119.3	C19—C18—H18	121.0
C9—C8—C7	118.15 (19)	C14—C19—C18	121.55 (19)
C9—C8—H8	120.9	C14—C19—H19	119.2
C7—C8—H8	120.9	C18—C19—H19	119.2
F1—C9—C10	118.7 (2)	C5—N1—C1	112.48 (13)
F1—C9—C8	118.9 (2)	C5—N1—H1A	123.8
C10—C9—C8	122.38 (18)	C1—N1—H1A	123.8
N1—C1—C2—C3	−53.46 (17)	C7—C8—C9—C10	−0.5 (3)
C6—C1—C2—C3	−176.73 (13)	F1—C9—C10—C11	−179.75 (17)
N1—C1—C2—C12	179.98 (15)	C8—C9—C10—C11	0.4 (3)
C6—C1—C2—C12	56.71 (19)	C9—C10—C11—C6	0.8 (3)
C12—C2—C3—O1	−3.1 (3)	C7—C6—C11—C10	−1.8 (3)
C1—C2—C3—O1	−129.78 (18)	C1—C6—C11—C10	173.17 (16)
C12—C2—C3—C4	176.70 (16)	N1—C5—C14—C19	50.64 (19)
C1—C2—C3—C4	50.01 (19)	C4—C5—C14—C19	−70.19 (19)
O1—C3—C4—C13	3.0 (3)	N1—C5—C14—C15	−130.90 (16)
C2—C3—C4—C13	−176.83 (16)	C4—C5—C14—C15	108.27 (18)
O1—C3—C4—C5	129.00 (18)	C19—C14—C15—C16	0.2 (3)
C2—C3—C4—C5	−50.79 (19)	C5—C14—C15—C16	−178.30 (17)
C3—C4—C5—N1	55.74 (18)	C14—C15—C16—C17	−0.1 (3)
C13—C4—C5—N1	−179.19 (16)	C15—C16—C17—C18	0.0 (4)
C3—C4—C5—C14	178.09 (13)	C15—C16—C17—F2	−179.76 (19)
C13—C4—C5—C14	−56.8 (2)	C16—C17—C18—C19	0.0 (4)
N1—C1—C6—C7	−50.19 (19)	F2—C17—C18—C19	179.78 (18)
C2—C1—C6—C7	70.83 (18)	C15—C14—C19—C18	−0.2 (3)
N1—C1—C6—C11	135.01 (16)	C5—C14—C19—C18	178.32 (16)
C2—C1—C6—C11	−103.97 (17)	C17—C18—C19—C14	0.1 (3)
C11—C6—C7—C8	1.7 (2)	C14—C5—N1—C1	171.33 (12)
C1—C6—C7—C8	−173.18 (15)	C4—C5—N1—C1	−66.12 (17)
C6—C7—C8—C9	−0.6 (3)	C6—C1—N1—C5	−173.32 (12)
C7—C8—C9—F1	179.65 (16)	C2—C1—N1—C5	64.62 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1i	0.93	2.49	3.400 (3)	165
C18—H18···F1ii	0.93	2.54	3.197 (3)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1i	0.93	2.49	3.400 (3)	165
C18—H18⋯F1ii	0.93	2.54	3.197 (3)	128

Symmetry codes: (i) ; (ii) .