N-[4-Chloro-3-(trifluoro-meth-yl)phen-yl]-2,2-dimethyl-propanamide.

In the title compound, C(12)H(13)ClF(3)NO, the C-C-N-C torsion angle between the benzene ring and the pivaloyl group is -33.9 (5)°. In the crystal, molecules are linked via N-H⋯O hydrogen bonds to form chains running parallel to the c axis. Weak van der Waals inter-actions are also observed.

Related literature

For background information on related compounds, see: Rosenblum et al. (1998 ▶); Wang et al. (2009 ▶). For a related crystal structure, see: Zhu et al. (2007 ▶).

Experimental

Crystal data

C12H13ClF3NO

M = 279.68

Monoclinic,

a = 5.8850 (12) Å

b = 21.955 (4) Å

c = 10.307 (2) Å

β = 104.50 (3)°

V = 1289.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.32 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 = 0.910, T max = 0.969

2599 measured reflections

2364 independent reflections

1477 reflections with I > 2σ(I)

R int = 0.052

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.192

S = 1.00

2364 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 EXPRESS; 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/S1600536812031650/pk2427sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031650/pk2427Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812031650/pk2427Isup3.cml

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

C12H13ClF3NO	F(000) = 576
Mr = 279.68	Dx = 1.441 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 5.8850 (12) Å	θ = 10–13°
b = 21.955 (4) Å	µ = 0.32 mm−1
c = 10.307 (2) Å	T = 293 K
β = 104.50 (3)°	Block, colorless
V = 1289.3 (5) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1477 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.052
Graphite monochromator	θmax = 25.4°, θmin = 1.9°
ω/2θ scans	h = 0→7
Absorption correction: ψ scan (North et al., 1968)	k = 0→26
Tmin = 0.910, Tmax = 0.969	l = −12→12
2599 measured reflections	3 standard reflections every 200 reflections
2364 independent reflections	intensity decay: 1%

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.192	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1P)2 + 0.6P] where P = (Fo2 + 2Fc2)/3
2364 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.38 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.

	x	y	z	Uiso*/Ueq
Cl	0.8303 (2)	0.49337 (6)	0.12942 (14)	0.0873 (5)
O	0.1944 (5)	0.25926 (12)	0.2729 (2)	0.0647 (8)
N	0.2134 (5)	0.27644 (13)	0.0605 (3)	0.0494 (7)
H0A	0.1632	0.2645	−0.0211	0.059*
F1	0.7046 (6)	0.47123 (13)	0.3967 (3)	0.1021 (10)
C1	0.4957 (8)	0.46500 (17)	0.3095 (4)	0.0639 (11)
F2	0.3471 (6)	0.44832 (12)	0.3808 (3)	0.1073 (11)
C2	0.5006 (6)	0.42126 (16)	0.1992 (3)	0.0483 (9)
F3	0.4298 (5)	0.52091 (10)	0.2663 (3)	0.0797 (8)
C3	0.3567 (6)	0.37039 (15)	0.1826 (3)	0.0474 (9)
H3A	0.2576	0.3643	0.2389	0.057*
C4	0.3598 (6)	0.32856 (15)	0.0826 (3)	0.0444 (8)
C5	0.5033 (7)	0.33915 (17)	−0.0024 (3)	0.0540 (9)
H5A	0.5024	0.3120	−0.0718	0.065*
C6	0.6482 (7)	0.38958 (19)	0.0147 (4)	0.0623 (11)
H6A	0.7468	0.3957	−0.0420	0.075*
C7	0.6471 (6)	0.43065 (17)	0.1149 (4)	0.0542 (9)
C8	0.1439 (6)	0.24321 (15)	0.1556 (3)	0.0442 (8)
C9	0.0085 (6)	0.18476 (15)	0.1083 (3)	0.0463 (8)
C10	0.1853 (9)	0.1369 (2)	0.0953 (7)	0.107 (2)
H10A	0.2984	0.1321	0.1798	0.161*
H10B	0.2638	0.1493	0.0284	0.161*
H10C	0.1063	0.0989	0.0694	0.161*
C11	−0.1150 (11)	0.1652 (3)	0.2130 (5)	0.110 (2)
H11A	−0.0022	0.1605	0.2976	0.165*
H11B	−0.1931	0.1270	0.1872	0.165*
H11C	−0.2283	0.1955	0.2210	0.165*
C12	−0.1714 (9)	0.1921 (2)	−0.0249 (5)	0.0984 (18)
H12A	−0.0938	0.2042	−0.0923	0.148*
H12B	−0.2838	0.2226	−0.0166	0.148*
H12C	−0.2504	0.1540	−0.0500	0.148*

	U11	U22	U33	U12	U13	U23
Cl	0.0823 (8)	0.0705 (8)	0.1155 (10)	−0.0271 (6)	0.0370 (7)	−0.0055 (7)
O	0.107 (2)	0.0532 (16)	0.0354 (13)	−0.0215 (15)	0.0202 (13)	−0.0028 (11)
N	0.074 (2)	0.0427 (16)	0.0316 (13)	−0.0087 (14)	0.0141 (13)	−0.0051 (12)
F1	0.136 (3)	0.078 (2)	0.0703 (16)	0.0004 (17)	−0.0147 (17)	−0.0234 (14)
C1	0.095 (3)	0.043 (2)	0.055 (2)	−0.011 (2)	0.021 (2)	−0.0062 (18)
F2	0.196 (3)	0.0666 (17)	0.0886 (18)	−0.0380 (19)	0.090 (2)	−0.0322 (14)
C2	0.062 (2)	0.0390 (19)	0.0420 (18)	0.0023 (16)	0.0098 (16)	0.0041 (15)
F3	0.105 (2)	0.0383 (13)	0.0994 (18)	0.0013 (12)	0.0319 (15)	−0.0087 (12)
C3	0.068 (2)	0.0380 (19)	0.0395 (17)	−0.0036 (16)	0.0199 (16)	0.0009 (14)
C4	0.060 (2)	0.0382 (18)	0.0355 (17)	0.0003 (15)	0.0126 (15)	0.0012 (14)
C5	0.074 (2)	0.046 (2)	0.0458 (19)	0.0035 (18)	0.0225 (18)	−0.0040 (16)
C6	0.070 (3)	0.060 (2)	0.067 (2)	−0.004 (2)	0.035 (2)	0.002 (2)
C7	0.058 (2)	0.043 (2)	0.061 (2)	−0.0044 (17)	0.0159 (18)	0.0035 (18)
C8	0.060 (2)	0.0380 (18)	0.0351 (18)	0.0023 (15)	0.0136 (15)	0.0013 (14)
C9	0.057 (2)	0.0368 (18)	0.0441 (18)	−0.0022 (15)	0.0118 (15)	0.0005 (15)
C10	0.082 (3)	0.048 (3)	0.186 (6)	0.002 (2)	0.021 (4)	−0.032 (3)
C11	0.144 (5)	0.113 (4)	0.088 (3)	−0.075 (4)	0.056 (3)	−0.027 (3)
C12	0.106 (4)	0.073 (3)	0.090 (3)	−0.028 (3)	−0.026 (3)	0.009 (3)

Cl—C7	1.732 (4)	C6—C7	1.372 (5)
O—C8	1.222 (4)	C6—H6A	0.9300
N—C8	1.364 (4)	C8—C9	1.525 (5)
N—C4	1.416 (4)	C9—C11	1.506 (6)
N—H0A	0.8600	C9—C10	1.508 (6)
F1—C1	1.336 (5)	C9—C12	1.518 (5)
C1—F2	1.326 (5)	C10—H10A	0.9600
C1—F3	1.330 (4)	C10—H10B	0.9600
C1—C2	1.494 (5)	C10—H10C	0.9600
C2—C7	1.385 (5)	C11—H11A	0.9600
C2—C3	1.386 (5)	C11—H11B	0.9600
C3—C4	1.384 (4)	C11—H11C	0.9600
C3—H3A	0.9300	C12—H12A	0.9600
C4—C5	1.379 (5)	C12—H12B	0.9600
C5—C6	1.382 (5)	C12—H12C	0.9600
C5—H5A	0.9300
C8—N—C4	126.6 (3)	O—C8—N	120.9 (3)
C8—N—H0A	116.7	O—C8—C9	122.5 (3)
C4—N—H0A	116.7	N—C8—C9	116.6 (3)
F2—C1—F3	105.3 (4)	C11—C9—C10	109.4 (4)
F2—C1—F1	106.2 (3)	C11—C9—C12	109.0 (4)
F3—C1—F1	105.8 (3)	C10—C9—C12	109.5 (4)
F2—C1—C2	112.6 (3)	C11—C9—C8	108.6 (3)
F3—C1—C2	113.4 (3)	C10—C9—C8	107.3 (3)
F1—C1—C2	112.8 (4)	C12—C9—C8	113.0 (3)
C7—C2—C3	119.9 (3)	C9—C10—H10A	109.5
C7—C2—C1	121.1 (3)	C9—C10—H10B	109.5
C3—C2—C1	119.0 (3)	H10A—C10—H10B	109.5
C4—C3—C2	120.4 (3)	C9—C10—H10C	109.5
C4—C3—H3A	119.8	H10A—C10—H10C	109.5
C2—C3—H3A	119.8	H10B—C10—H10C	109.5
C5—C4—C3	119.0 (3)	C9—C11—H11A	109.5
C5—C4—N	118.6 (3)	C9—C11—H11B	109.5
C3—C4—N	122.3 (3)	H11A—C11—H11B	109.5
C4—C5—C6	120.7 (3)	C9—C11—H11C	109.5
C4—C5—H5A	119.6	H11A—C11—H11C	109.5
C6—C5—H5A	119.6	H11B—C11—H11C	109.5
C7—C6—C5	120.2 (3)	C9—C12—H12A	109.5
C7—C6—H6A	119.9	C9—C12—H12B	109.5
C5—C6—H6A	119.9	H12A—C12—H12B	109.5
C6—C7—C2	119.7 (3)	C9—C12—H12C	109.5
C6—C7—Cl	117.8 (3)	H12A—C12—H12C	109.5
C2—C7—Cl	122.4 (3)	H12B—C12—H12C	109.5
F2—C1—C2—C7	−179.3 (4)	C5—C6—C7—C2	0.2 (6)
F3—C1—C2—C7	61.3 (5)	C5—C6—C7—Cl	−179.2 (3)
F1—C1—C2—C7	−59.1 (5)	C3—C2—C7—C6	0.3 (5)
F2—C1—C2—C3	0.2 (5)	C1—C2—C7—C6	179.8 (4)
F3—C1—C2—C3	−119.2 (4)	C3—C2—C7—Cl	179.7 (3)
F1—C1—C2—C3	120.5 (4)	C1—C2—C7—Cl	−0.8 (5)
C7—C2—C3—C4	0.5 (5)	C4—N—C8—O	4.8 (5)
C1—C2—C3—C4	−179.0 (3)	C4—N—C8—C9	−173.3 (3)
C2—C3—C4—C5	−1.8 (5)	O—C8—C9—C11	19.1 (5)
C2—C3—C4—N	−179.0 (3)	N—C8—C9—C11	−162.8 (4)
C8—N—C4—C5	148.6 (3)	O—C8—C9—C10	−99.1 (5)
C8—N—C4—C3	−34.1 (5)	N—C8—C9—C10	79.0 (4)
C3—C4—C5—C6	2.3 (5)	O—C8—C9—C12	140.2 (4)
N—C4—C5—C6	179.6 (3)	N—C8—C9—C12	−41.7 (5)
C4—C5—C6—C7	−1.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···O	0.86	2.24	3.041 (4)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯O	0.86	2.24	3.041 (4)	155