4-Meth-oxy-3-(trifluoro-meth-yl)aniline.

In title compound, C(8)H(8)F(3)NO, the meth-oxy group is inclined at 8.7 (4)° to the benzene ring plane. The crystal structure is stabilized by inter-molecular N-H⋯F, N-H⋯N and C-H⋯F hydrogen-bonding inter-actions.

Related literature

The title compound is an inter­mediate in the synthesis of trifluoro­methyl-containing phthalic acid diamides, which are effective pesticides. For the preparation, see: Feng & Li (2010 ▶). For the crystal structure of a closely related compound, see: Crampton et al. (2006 ▶).

Experimental

Crystal data

C8H8F3NO

M = 191.15

Orthorhombic,

a = 5.4140 (11) Å

b = 14.880 (3) Å

c = 21.304 (4) Å

V = 1716.3 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.14 mm−1

T = 293 K

0.10 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.986, T max = 0.986

1722 measured reflections

1722 independent reflections

1389 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.162

S = 1.13

1722 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); 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: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681200030X/pv2499sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200030X/pv2499Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681200030X/pv2499Isup3.cml

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

C8H8F3NO	F(000) = 784
Mr = 191.15	Dx = 1.480 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 5.4140 (11) Å	θ = 3.3–20.0°
b = 14.880 (3) Å	µ = 0.14 mm−1
c = 21.304 (4) Å	T = 293 K
V = 1716.3 (6) Å3	Prism, colorless
Z = 8	0.10 × 0.10 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	1722 independent reflections
Radiation source: fine-focus sealed tube	1389 reflections with I > 2σ(I)
graphite	Rint = 0.0000
Detector resolution: 28.5714 pixels mm-1	θmax = 26.4°, θmin = 3.3°
ω/2θ scans	h = 0→6
Absorption correction: ψ scan (North et al., 1968)	k = 0→18
Tmin = 0.986, Tmax = 0.986	l = 0→26
1722 measured reflections

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.074P)2 + 0.3348P] where P = (Fo2 + 2Fc2)/3
1722 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.19 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
N	0.0910 (3)	0.09833 (11)	0.20799 (9)	0.0642 (5)
H0A	0.1826	0.0524	0.2003	0.077*
H0B	0.0020	0.0998	0.2414	0.077*
F3	−0.3126 (4)	0.39455 (11)	0.21116 (7)	0.1021 (6)
F2	−0.3656 (3)	0.42452 (10)	0.11387 (8)	0.0906 (5)
C7	−0.0486 (4)	0.32133 (13)	0.13969 (9)	0.0548 (5)
F1	−0.0537 (3)	0.47609 (9)	0.16277 (8)	0.0924 (6)
O	0.0805 (4)	0.39518 (12)	0.04733 (8)	0.0872 (6)
C6	−0.0515 (4)	0.24725 (13)	0.17919 (10)	0.0550 (5)
H6A	−0.1479	0.2487	0.2153	0.066*
C5	0.0868 (4)	0.17085 (13)	0.16592 (9)	0.0557 (5)
C8	−0.1937 (4)	0.40274 (15)	0.15659 (10)	0.0643 (6)
C2	0.0907 (4)	0.32022 (15)	0.08453 (10)	0.0653 (6)
C4	0.2268 (5)	0.17158 (16)	0.11146 (11)	0.0719 (7)
H4A	0.3216	0.1214	0.1016	0.086*
C3	0.2297 (5)	0.24452 (18)	0.07140 (11)	0.0767 (7)
H3A	0.3260	0.2427	0.0353	0.092*
C1	0.2463 (6)	0.4017 (2)	−0.00398 (11)	0.0865 (8)
H1A	0.2177	0.4570	−0.0260	0.130*
H1B	0.2203	0.3520	−0.0319	0.130*
H1C	0.4131	0.4005	0.0113	0.130*

	U11	U22	U33	U12	U13	U23
N	0.0752 (12)	0.0474 (10)	0.0699 (11)	0.0025 (8)	0.0031 (9)	0.0081 (8)
F3	0.1383 (15)	0.0767 (10)	0.0912 (11)	0.0339 (10)	0.0413 (10)	0.0151 (8)
F2	0.0887 (10)	0.0811 (11)	0.1018 (11)	0.0177 (8)	−0.0227 (9)	0.0065 (8)
C7	0.0605 (11)	0.0477 (11)	0.0562 (11)	−0.0037 (9)	−0.0035 (10)	0.0018 (8)
F1	0.1106 (12)	0.0541 (8)	0.1124 (12)	−0.0104 (8)	−0.0073 (9)	−0.0123 (7)
O	0.1094 (14)	0.0758 (11)	0.0763 (11)	0.0142 (10)	0.0150 (10)	0.0304 (9)
C6	0.0620 (12)	0.0492 (11)	0.0539 (11)	−0.0033 (9)	0.0009 (10)	0.0014 (8)
C5	0.0625 (12)	0.0482 (11)	0.0563 (11)	−0.0046 (9)	−0.0058 (10)	0.0021 (8)
C8	0.0757 (15)	0.0539 (12)	0.0632 (12)	0.0042 (10)	0.0003 (11)	0.0069 (10)
C2	0.0782 (14)	0.0604 (13)	0.0572 (12)	0.0005 (11)	0.0006 (11)	0.0119 (10)
C4	0.0852 (16)	0.0629 (14)	0.0674 (13)	0.0141 (12)	0.0126 (13)	0.0032 (10)
C3	0.0922 (17)	0.0765 (16)	0.0614 (13)	0.0136 (13)	0.0179 (13)	0.0116 (11)
C1	0.0955 (18)	0.0942 (19)	0.0697 (15)	−0.0139 (15)	0.0077 (15)	0.0258 (14)

N—C5	1.403 (3)	C6—C5	1.390 (3)
N—H0A	0.8600	C6—H6A	0.9300
N—H0B	0.8600	C5—C4	1.386 (3)
F3—C8	1.335 (3)	C2—C3	1.383 (3)
F2—C8	1.342 (3)	C4—C3	1.381 (3)
C7—C6	1.387 (3)	C4—H4A	0.9300
C7—C2	1.396 (3)	C3—H3A	0.9300
C7—C8	1.488 (3)	C1—H1A	0.9600
F1—C8	1.335 (3)	C1—H1B	0.9600
O—C2	1.369 (3)	C1—H1C	0.9600
O—C1	1.418 (3)
C5—N—H0A	120.0	F1—C8—C7	112.9 (2)
C5—N—H0B	120.0	F2—C8—C7	113.50 (19)
H0A—N—H0B	120.0	O—C2—C3	124.6 (2)
C6—C7—C2	120.48 (19)	O—C2—C7	117.1 (2)
C6—C7—C8	119.62 (19)	C3—C2—C7	118.27 (19)
C2—C7—C8	119.89 (18)	C3—C4—C5	122.0 (2)
C2—O—C1	118.4 (2)	C3—C4—H4A	119.0
C7—C6—C5	121.37 (19)	C5—C4—H4A	119.0
C7—C6—H6A	119.3	C4—C3—C2	120.6 (2)
C5—C6—H6A	119.3	C4—C3—H3A	119.7
C4—C5—C6	117.27 (18)	C2—C3—H3A	119.7
C4—C5—N	122.13 (19)	O—C1—H1A	109.5
C6—C5—N	120.53 (19)	O—C1—H1B	109.5
F3—C8—F1	105.23 (19)	H1A—C1—H1B	109.5
F3—C8—F2	106.14 (19)	O—C1—H1C	109.5
F1—C8—F2	105.25 (18)	H1A—C1—H1C	109.5
F3—C8—C7	113.03 (18)	H1B—C1—H1C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1C···F2i	0.96	2.52	3.292 (3)	138
C6—H6A···F3	0.93	2.35	2.696 (3)	102
N—H0A···F1ii	0.86	2.44	3.242 (2)	155
N—H0B···Niii	0.86	2.47	3.245 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1C⋯F2i	0.96	2.52	3.292 (3)	138
N—H0A⋯F1ii	0.86	2.44	3.242 (2)	155
N—H0B⋯Niii	0.86	2.47	3.245 (3)	150

Symmetry codes: (i) ; (ii) ; (iii) .