N-(4-Fluoro-phen-yl)-2,2-dimethyl-propan-amide.

The crystal packing in the title compound, C(11)H(14)FNO, features N-H⋯O hydrogen bonds, resulting in chains of mol-ecules running parallel to the c axis. The dihedral angle between the ring and the amide group is 39.1 (3)°.

Related literature

The title compound is an inter­mediate in the synthesis of ezetimibe, which inhibits the absorption of cholesterol from the intestine, see: Rosenblum et al. (1998 ▶). For the synthesis, see: Wang et al. (2008 ▶). For a related structure, see: Gowda et al. (2007 ▶).

Experimental

Crystal data

C11H14FNO

M = 195.23

Monoclinic,

a = 9.5750 (19) Å

b = 13.027 (3) Å

c = 8.8340 (18) Å

β = 92.07 (3)°

V = 1101.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.974, T max = 0.991

4219 measured reflections

2025 independent reflections

1091 reflections with I > 2σ(I)

R int = 0.082

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.155

S = 1.00

2025 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812020570/pv2534sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020570/pv2534Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812020570/pv2534Isup3.cml

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

C11H14FNO	F(000) = 416
Mr = 195.23	Dx = 1.178 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.5750 (19) Å	θ = 10–13°
b = 13.027 (3) Å	µ = 0.09 mm−1
c = 8.8340 (18) Å	T = 293 K
β = 92.07 (3)°	Block, yellow
V = 1101.2 (4) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1091 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.082
Graphite monochromator	θmax = 25.4°, θmin = 2.1°
ω/2θ scans	h = −11→11
Absorption correction: ψ scan (North et al., 1968)	k = −15→15
Tmin = 0.974, Tmax = 0.991	l = 0→10
4219 measured reflections	3 standard reflections every 200 reflections
2025 independent reflections	intensity decay: 1%

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)] = 0.062	H-atom parameters constrained
wR(F2) = 0.155	w = 1/[σ2(Fo2) + (0.065P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2025 reflections	Δρmax = 0.20 e Å−3
128 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.020 (5)

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
O	0.55665 (18)	0.65320 (14)	0.18951 (19)	0.0619 (6)
F	0.01604 (17)	0.92797 (16)	0.1759 (2)	0.1032 (7)
N	0.4924 (2)	0.74067 (17)	−0.0211 (2)	0.0588 (7)
H0A	0.5136	0.7547	−0.1126	0.071*
C1	0.2795 (3)	0.7359 (2)	0.1236 (3)	0.0638 (8)
H1A	0.2982	0.6683	0.1514	0.077*
C2	0.1603 (3)	0.7837 (3)	0.1726 (4)	0.0728 (9)
H2A	0.0995	0.7493	0.2349	0.087*
C3	0.1340 (3)	0.8806 (3)	0.1284 (3)	0.0693 (9)
C4	0.2195 (3)	0.9346 (2)	0.0395 (3)	0.0731 (9)
H4A	0.1981	1.0016	0.0110	0.088*
C5	0.3409 (3)	0.8869 (2)	−0.0081 (3)	0.0640 (8)
H5A	0.4019	0.9225	−0.0687	0.077*
C6	0.3705 (3)	0.7878 (2)	0.0339 (3)	0.0507 (7)
C7	0.5775 (3)	0.6763 (2)	0.0568 (3)	0.0496 (7)
C8	0.7023 (3)	0.6356 (2)	−0.0266 (3)	0.0560 (7)
C9	0.8029 (3)	0.7255 (3)	−0.0500 (4)	0.0864 (11)
H9A	0.8316	0.7537	0.0465	0.130*
H9B	0.7565	0.7775	−0.1102	0.130*
H9C	0.8834	0.7014	−0.1011	0.130*
C10	0.7752 (4)	0.5529 (3)	0.0688 (4)	0.1008 (13)
H10A	0.7121	0.4967	0.0829	0.151*
H10B	0.8036	0.5809	0.1657	0.151*
H10C	0.8560	0.5289	0.0181	0.151*
C11	0.6568 (3)	0.5904 (2)	−0.1808 (3)	0.0759 (10)
H11A	0.5945	0.5338	−0.1662	0.114*
H11B	0.7375	0.5669	−0.2321	0.114*
H11C	0.6097	0.6422	−0.2408	0.114*

	U11	U22	U33	U12	U13	U23
O	0.0662 (12)	0.0774 (14)	0.0430 (11)	0.0127 (10)	0.0146 (9)	0.0049 (10)
F	0.0656 (12)	0.1364 (17)	0.1092 (15)	0.0362 (11)	0.0246 (11)	−0.0114 (13)
N	0.0603 (14)	0.0756 (15)	0.0418 (12)	0.0164 (13)	0.0204 (11)	0.0052 (12)
C1	0.0579 (17)	0.071 (2)	0.0637 (18)	0.0048 (15)	0.0160 (15)	0.0065 (15)
C2	0.0509 (17)	0.099 (3)	0.070 (2)	0.0022 (18)	0.0194 (15)	0.0051 (19)
C3	0.0507 (17)	0.095 (2)	0.0631 (18)	0.0197 (18)	0.0119 (15)	−0.0072 (18)
C4	0.073 (2)	0.073 (2)	0.073 (2)	0.0218 (18)	0.0069 (17)	0.0059 (17)
C5	0.0660 (19)	0.071 (2)	0.0564 (17)	0.0073 (16)	0.0177 (14)	0.0078 (15)
C6	0.0519 (15)	0.0640 (18)	0.0370 (13)	0.0053 (14)	0.0113 (12)	−0.0002 (13)
C7	0.0537 (16)	0.0574 (17)	0.0384 (14)	0.0016 (13)	0.0114 (12)	−0.0005 (13)
C8	0.0548 (16)	0.0679 (19)	0.0461 (15)	0.0087 (14)	0.0119 (12)	−0.0050 (14)
C9	0.0548 (18)	0.112 (3)	0.093 (3)	−0.0102 (18)	0.0193 (18)	−0.023 (2)
C10	0.097 (2)	0.125 (3)	0.082 (2)	0.059 (2)	0.022 (2)	0.014 (2)
C11	0.080 (2)	0.082 (2)	0.067 (2)	0.0074 (18)	0.0224 (16)	−0.0181 (17)

O—C7	1.233 (3)	C5—H5A	0.9300
F—C3	1.366 (3)	C7—C8	1.522 (3)
N—C7	1.342 (3)	C8—C10	1.522 (4)
N—C6	1.420 (3)	C8—C11	1.533 (4)
N—H0A	0.8600	C8—C9	1.535 (4)
C1—C6	1.376 (4)	C9—H9A	0.9600
C1—C2	1.383 (4)	C9—H9B	0.9600
C1—H1A	0.9300	C9—H9C	0.9600
C2—C3	1.343 (4)	C10—H10A	0.9600
C2—H2A	0.9300	C10—H10B	0.9600
C3—C4	1.352 (4)	C10—H10C	0.9600
C4—C5	1.397 (4)	C11—H11A	0.9600
C4—H4A	0.9300	C11—H11B	0.9600
C5—C6	1.371 (4)	C11—H11C	0.9600
C7—N—C6	125.9 (2)	C7—C8—C10	109.3 (2)
C7—N—H0A	117.1	C7—C8—C11	111.2 (2)
C6—N—H0A	117.1	C10—C8—C11	109.3 (2)
C6—C1—C2	120.4 (3)	C7—C8—C9	107.9 (2)
C6—C1—H1A	119.8	C10—C8—C9	109.7 (3)
C2—C1—H1A	119.8	C11—C8—C9	109.4 (2)
C3—C2—C1	118.7 (3)	C8—C9—H9A	109.5
C3—C2—H2A	120.6	C8—C9—H9B	109.5
C1—C2—H2A	120.6	H9A—C9—H9B	109.5
C2—C3—C4	123.1 (3)	C8—C9—H9C	109.5
C2—C3—F	118.9 (3)	H9A—C9—H9C	109.5
C4—C3—F	117.9 (3)	H9B—C9—H9C	109.5
C3—C4—C5	118.2 (3)	C8—C10—H10A	109.5
C3—C4—H4A	120.9	C8—C10—H10B	109.5
C5—C4—H4A	120.9	H10A—C10—H10B	109.5
C6—C5—C4	120.2 (3)	C8—C10—H10C	109.5
C6—C5—H5A	119.9	H10A—C10—H10C	109.5
C4—C5—H5A	119.9	H10B—C10—H10C	109.5
C5—C6—C1	119.3 (2)	C8—C11—H11A	109.5
C5—C6—N	118.6 (2)	C8—C11—H11B	109.5
C1—C6—N	122.0 (3)	H11A—C11—H11B	109.5
O—C7—N	121.6 (2)	C8—C11—H11C	109.5
O—C7—C8	122.1 (2)	H11A—C11—H11C	109.5
N—C7—C8	116.3 (2)	H11B—C11—H11C	109.5
C6—C1—C2—C3	1.4 (5)	C7—N—C6—C5	142.3 (3)
C1—C2—C3—C4	−0.9 (5)	C7—N—C6—C1	−39.9 (4)
C1—C2—C3—F	179.7 (3)	C6—N—C7—O	−1.2 (4)
C2—C3—C4—C5	0.0 (5)	C6—N—C7—C8	−179.9 (2)
F—C3—C4—C5	179.4 (2)	O—C7—C8—C10	9.3 (4)
C3—C4—C5—C6	0.5 (4)	N—C7—C8—C10	−172.0 (3)
C4—C5—C6—C1	0.0 (4)	O—C7—C8—C11	130.1 (3)
C4—C5—C6—N	177.8 (2)	N—C7—C8—C11	−51.3 (3)
C2—C1—C6—C5	−0.9 (4)	O—C7—C8—C9	−110.0 (3)
C2—C1—C6—N	−178.7 (2)	N—C7—C8—C9	68.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···Oi	0.86	2.17	2.990 (3)	159
C1—H1A···O	0.93	2.49	2.904 (3)	107

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯Oi	0.86	2.17	2.990 (3)	159

Symmetry code: (i) .