(2,6-Difluoro-phen-yl)(4-methyl-piperidin-1-yl)methanone.

In the title compound, C(13)H(15)F(2)NO, the piperidine ring adopts a chair conformation. The dihedral angle between the least-squares plane of the piperidine ring and the benzene ring is 48.75 (7)°. In the crystal structure, the mol-ecules are connected via C-H⋯O hydrogen bonds, forming a zigzag chain along the b axis.

Related literature

For the biological applications of piperidine derivatives, see: Waelbroeck et al. (1992 ▶); El Hadri et al. (1995 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C13H15F2NO

M = 239.26

Monoclinic,

a = 9.1807 (7) Å

b = 10.9910 (8) Å

c = 13.2477 (8) Å

β = 115.582 (4)°

V = 1205.71 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.43 × 0.38 × 0.19 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.956, T max = 0.981

11030 measured reflections

3513 independent reflections

2617 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.136

S = 1.06

3513 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811033848/is2763sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033848/is2763Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033848/is2763Isup3.cml

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

C13H15F2NO	F(000) = 504
Mr = 239.26	Dx = 1.318 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4002 reflections
a = 9.1807 (7) Å	θ = 2.5–29.6°
b = 10.9910 (8) Å	µ = 0.10 mm−1
c = 13.2477 (8) Å	T = 296 K
β = 115.582 (4)°	Block, colourless
V = 1205.71 (15) Å3	0.43 × 0.38 × 0.19 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	3513 independent reflections
Radiation source: fine-focus sealed tube	2617 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scans	θmax = 30.1°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
Tmin = 0.956, Tmax = 0.981	k = −13→15
11030 measured reflections	l = −18→18

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0678P)2 + 0.1308P] where P = (Fo2 + 2Fc2)/3
3513 reflections	(Δ/σ)max = 0.001
155 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.20 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
F1	0.26788 (12)	0.67786 (9)	0.26565 (7)	0.0733 (3)
F2	0.16103 (13)	0.89859 (9)	0.52606 (7)	0.0835 (3)
O1	0.23349 (12)	0.59626 (9)	0.48443 (8)	0.0697 (3)
N1	0.46198 (12)	0.70862 (9)	0.55150 (9)	0.0528 (3)
C1	0.19420 (13)	0.77289 (11)	0.28922 (9)	0.0476 (3)
C2	0.10112 (15)	0.85157 (14)	0.20507 (10)	0.0600 (4)
H2A	0.0896	0.8407	0.1324	0.072*
C3	0.02604 (15)	0.94608 (15)	0.23065 (12)	0.0638 (4)
H3A	−0.0384	0.9992	0.1744	0.077*
C4	0.04459 (16)	0.96375 (14)	0.33859 (12)	0.0625 (4)
H4A	−0.0058	1.0283	0.3562	0.075*
C5	0.13981 (15)	0.88297 (12)	0.41937 (10)	0.0517 (3)
C6	0.21693 (12)	0.78571 (10)	0.39862 (8)	0.0413 (2)
C7	0.30603 (14)	0.68901 (10)	0.48395 (9)	0.0455 (3)
C8	0.54606 (14)	0.82462 (12)	0.56603 (10)	0.0526 (3)
H8A	0.4746	0.8839	0.5139	0.063*
H8B	0.6391	0.8145	0.5502	0.063*
C9	0.60040 (14)	0.86998 (11)	0.68488 (10)	0.0504 (3)
H9A	0.5064	0.8871	0.6981	0.060*
H9B	0.6604	0.9451	0.6946	0.060*
C10	0.70612 (14)	0.77668 (11)	0.76970 (10)	0.0503 (3)
H10A	0.8025	0.7636	0.7570	0.060*
C11	0.61572 (15)	0.65643 (11)	0.74973 (11)	0.0563 (3)
H11A	0.6864	0.5953	0.7997	0.068*
H11B	0.5238	0.6660	0.7670	0.068*
C12	0.55722 (17)	0.61347 (11)	0.62987 (11)	0.0631 (4)
H12A	0.6493	0.5925	0.6156	0.076*
H12B	0.4915	0.5411	0.6185	0.076*
C13	0.7612 (2)	0.82022 (17)	0.88950 (12)	0.0781 (5)
H13A	0.8241	0.8931	0.9009	0.117*
H13B	0.8258	0.7583	0.9402	0.117*
H13C	0.6686	0.8368	0.9031	0.117*

	U11	U22	U33	U12	U13	U23
F1	0.0883 (6)	0.0761 (6)	0.0598 (5)	0.0042 (5)	0.0360 (4)	−0.0189 (4)
F2	0.1137 (8)	0.0920 (7)	0.0538 (5)	0.0326 (6)	0.0448 (5)	0.0010 (4)
O1	0.0689 (6)	0.0515 (5)	0.0607 (6)	−0.0175 (4)	0.0017 (4)	0.0058 (4)
N1	0.0477 (5)	0.0406 (5)	0.0503 (5)	0.0007 (4)	0.0025 (4)	0.0013 (4)
C1	0.0445 (5)	0.0567 (7)	0.0384 (5)	−0.0074 (5)	0.0147 (4)	−0.0065 (4)
C2	0.0545 (7)	0.0820 (9)	0.0331 (5)	−0.0143 (6)	0.0091 (5)	0.0061 (5)
C3	0.0429 (6)	0.0752 (9)	0.0575 (7)	0.0000 (6)	0.0069 (5)	0.0263 (7)
C4	0.0511 (6)	0.0641 (8)	0.0702 (8)	0.0153 (6)	0.0243 (6)	0.0146 (6)
C5	0.0520 (6)	0.0601 (7)	0.0439 (6)	0.0077 (5)	0.0214 (5)	0.0032 (5)
C6	0.0380 (5)	0.0456 (5)	0.0350 (5)	−0.0021 (4)	0.0107 (4)	−0.0002 (4)
C7	0.0495 (6)	0.0409 (5)	0.0364 (5)	−0.0022 (4)	0.0093 (4)	−0.0035 (4)
C8	0.0447 (5)	0.0528 (7)	0.0501 (6)	−0.0060 (5)	0.0110 (5)	0.0037 (5)
C9	0.0463 (6)	0.0418 (6)	0.0578 (7)	−0.0074 (5)	0.0175 (5)	−0.0042 (5)
C10	0.0443 (5)	0.0553 (7)	0.0446 (6)	−0.0016 (5)	0.0130 (4)	−0.0039 (5)
C11	0.0523 (6)	0.0473 (6)	0.0547 (7)	0.0042 (5)	0.0094 (5)	0.0074 (5)
C12	0.0613 (7)	0.0417 (6)	0.0580 (7)	0.0084 (5)	−0.0009 (6)	−0.0013 (5)
C13	0.0974 (12)	0.0762 (10)	0.0507 (8)	−0.0106 (9)	0.0224 (8)	−0.0110 (7)

F1—C1	1.3522 (15)	C8—H8A	0.9700
F2—C5	1.3518 (14)	C8—H8B	0.9700
O1—C7	1.2192 (15)	C9—C10	1.5213 (17)
N1—C7	1.3381 (14)	C9—H9A	0.9700
N1—C8	1.4595 (16)	C9—H9B	0.9700
N1—C12	1.4671 (15)	C10—C13	1.5200 (18)
C1—C2	1.3777 (18)	C10—C11	1.5218 (18)
C1—C6	1.3795 (15)	C10—H10A	0.9800
C2—C3	1.368 (2)	C11—C12	1.5153 (19)
C2—H2A	0.9300	C11—H11A	0.9700
C3—C4	1.379 (2)	C11—H11B	0.9700
C3—H3A	0.9300	C12—H12A	0.9700
C4—C5	1.3747 (17)	C12—H12B	0.9700
C4—H4A	0.9300	C13—H13A	0.9600
C5—C6	1.3739 (17)	C13—H13B	0.9600
C6—C7	1.5094 (15)	C13—H13C	0.9600
C8—C9	1.5159 (17)
C7—N1—C8	125.53 (10)	C8—C9—C10	111.36 (10)
C7—N1—C12	119.81 (10)	C8—C9—H9A	109.4
C8—N1—C12	114.19 (9)	C10—C9—H9A	109.4
F1—C1—C2	119.69 (11)	C8—C9—H9B	109.4
F1—C1—C6	117.24 (11)	C10—C9—H9B	109.4
C2—C1—C6	123.06 (12)	H9A—C9—H9B	108.0
C3—C2—C1	118.63 (12)	C13—C10—C9	112.18 (12)
C3—C2—H2A	120.7	C13—C10—C11	111.45 (12)
C1—C2—H2A	120.7	C9—C10—C11	109.32 (9)
C2—C3—C4	120.94 (12)	C13—C10—H10A	107.9
C2—C3—H3A	119.5	C9—C10—H10A	107.9
C4—C3—H3A	119.5	C11—C10—H10A	107.9
C5—C4—C3	117.94 (13)	C12—C11—C10	111.88 (12)
C5—C4—H4A	121.0	C12—C11—H11A	109.2
C3—C4—H4A	121.0	C10—C11—H11A	109.2
F2—C5—C6	117.00 (10)	C12—C11—H11B	109.2
F2—C5—C4	119.21 (12)	C10—C11—H11B	109.2
C6—C5—C4	123.79 (12)	H11A—C11—H11B	107.9
C5—C6—C1	115.62 (10)	N1—C12—C11	110.65 (10)
C5—C6—C7	123.88 (10)	N1—C12—H12A	109.5
C1—C6—C7	120.14 (10)	C11—C12—H12A	109.5
O1—C7—N1	124.08 (11)	N1—C12—H12B	109.5
O1—C7—C6	118.17 (10)	C11—C12—H12B	109.5
N1—C7—C6	117.69 (10)	H12A—C12—H12B	108.1
N1—C8—C9	110.03 (10)	C10—C13—H13A	109.5
N1—C8—H8A	109.7	C10—C13—H13B	109.5
C9—C8—H8A	109.7	H13A—C13—H13B	109.5
N1—C8—H8B	109.7	C10—C13—H13C	109.5
C9—C8—H8B	109.7	H13A—C13—H13C	109.5
H8A—C8—H8B	108.2	H13B—C13—H13C	109.5
F1—C1—C2—C3	179.14 (11)	C8—N1—C7—C6	13.13 (19)
C6—C1—C2—C3	−0.79 (19)	C12—N1—C7—C6	−175.26 (11)
C1—C2—C3—C4	0.9 (2)	C5—C6—C7—O1	94.43 (15)
C2—C3—C4—C5	−0.5 (2)	C1—C6—C7—O1	−78.49 (15)
C3—C4—C5—F2	179.55 (13)	C5—C6—C7—N1	−88.19 (15)
C3—C4—C5—C6	−0.2 (2)	C1—C6—C7—N1	98.90 (13)
F2—C5—C6—C1	−179.40 (11)	C7—N1—C8—C9	115.22 (13)
C4—C5—C6—C1	0.35 (19)	C12—N1—C8—C9	−56.81 (15)
F2—C5—C6—C7	7.40 (18)	N1—C8—C9—C10	56.43 (13)
C4—C5—C6—C7	−172.86 (12)	C8—C9—C10—C13	−179.72 (12)
F1—C1—C6—C5	−179.77 (10)	C8—C9—C10—C11	−55.56 (14)
C2—C1—C6—C5	0.16 (17)	C13—C10—C11—C12	178.83 (12)
F1—C1—C6—C7	−6.30 (16)	C9—C10—C11—C12	54.25 (14)
C2—C1—C6—C7	173.64 (11)	C7—N1—C12—C11	−116.98 (13)
C8—N1—C7—O1	−169.65 (13)	C8—N1—C12—C11	55.54 (17)
C12—N1—C7—O1	2.0 (2)	C10—C11—C12—N1	−53.71 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O1i	0.93	2.35	3.2646 (18)	168.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O1i	0.93	2.35	3.2646 (18)	168

Symmetry code: (i) .