2,2,2-Tri­fluoro-N-(2-iodo­phen­yl)acetamide

Ruchun, Y.; Hui, Z.; BanPeng, C.

doi:10.1107/S1600536813029851

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 12| December 2013| Page o1749

doi:10.1107/S1600536813029851

Open

access

2,2,2-Trifluoro-N-(2-iodophenyl)acetamide

Yang Ruchun,^a ^* Zhang Hui ^a and Cao BanPeng ^a

^aJiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, People's Republic of China
^*Correspondence e-mail: ouyangruchun@aliyun.com

(Received 12 October 2013; accepted 31 October 2013; online 6 November 2013)

The three F atoms in the title compound, C₈H₅F₃INO, are disordered over two sets of sites [relative occupancies = 0.615 (14):0.385 (14)]. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, forming chains running along the c-axis direction. The dihedral angle between the ring and the amide group is 62.1 (3)°.

CCDC reference: 969598

Related literature

For effects of flourine on the properties of compounds, see: Jeschke (2004 ); Mueller et al. (2007 ); Purser et al. (2008 ). For the synthesis, see: Konfink et al. (2007 ).

Experimental

Crystal data

C₈H₅F₃INO
M_r = 315.02
Tetragonal, I 4₁ /a
a = 15.8871 (1) Å
c = 15.9300 (2) Å
V = 4020.7 (6) Å³
Z = 16
Mo Kα radiation
μ = 3.20 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.447, T_max = 0.567
6063 measured reflections
1775 independent reflections
1153 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.105
S = 1.06
1775 reflections
155 parameters
450 restraints
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.08	2.917 (6)	163
Symmetry code: (i) $[y+{\script{1\over 4}}, -x+{\script{5\over 4}}, z+{\script{1\over 4}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.

Supporting information

CCDC reference: 969598

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813029851/ff2122sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813029851/ff2122Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813029851/ff2122Isup3.cml

checkCIF report

Comment top

Aromatic compounds play an important role in the pharmaceutical and agrochemical industries as important intermediates. The fluorine atom has a strong electron withdrawing character and small atomic radius. Introduction of one or more F atoms can change the physiological activity, pharmacological activity and metabolic stability properties of the compound (Jeschke, 2004; Mueller, et al., 2007; Purser, et al., 2008). In our study, we report an aromatic compounds containing fluorine, 2,2,2-trifluoro-N-(2-iodophenyl)acetamide, which could be used in the synthesis of many bioactive compounds.

There is a single molecule in the asymmetric unit of the title compound 2,2,2-trifluoro-N-(2-iodophenyl)acetamide, C₈H₅F₃INO. In the crystal, The three F atoms are disordered over two sites [relative occupancies 0.615 (14):0.385 (14)]. The crystal packing is stabilized by N1—H1···O1 hydrogen bond that connect molecules into chains running along the c direction.

Related literature top

For effects of flourine on the properties of compounds, see: Jeschke (2004); Mueller et al. (2007); Purser et al. (2008). For the synthesis, see: Konfink et al. (2007). Mueller et al. (2007); Purser et al. (2008). For synthesis, see: Konfink et al. (2007).

Experimental top

The title compound was synthesized according to the previously reported procedure (Konfink, et al., 2007).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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 (Sheldrick, 2008).

Figures top

Fig. 1. Thermal ellipsoid plot of C₈H₅F₃INO. Ellipsoids are drawn at the 30% probability level and H atoms are represented as small spheres of arbitrary radius.

2,2,2-Trifluoro-N-(2-iodophenyl)acetamide top

Crystal data top

C₈H₅F₃INO	D_x = 2.075 Mg m⁻³
M_r = 315.02	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4₁/a	Cell parameters from 1114 reflections
Hall symbol: -I 4ad	θ = 3.1–21.8°
a = 15.8871 (1) Å	µ = 3.20 mm⁻¹
c = 15.9300 (2) Å	T = 293 K
V = 4020.7 (6) Å³	Block, colourless
Z = 16	0.30 × 0.20 × 0.20 mm
F(000) = 2368

Data collection top

Agilent Xcalibur (Eos, Gemini) diffractometer	1775 independent reflections
Radiation source: fine-focus sealed tube	1153 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
ω scans	θ_max = 25.0°, θ_min = 3.1°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −17→15
T_min = 0.447, T_max = 0.567	k = −18→12
6063 measured reflections	l = −18→18

Refinement top

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0324P)² + 3.0148P] where P = (F_o² + 2F_c²)/3
1775 reflections	(Δ/σ)_max < 0.001
155 parameters	Δρ_max = 0.42 e Å⁻³
450 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

C₈H₅F₃INO	Z = 16
M_r = 315.02	Mo Kα radiation
Tetragonal, I4₁/a	µ = 3.20 mm⁻¹
a = 15.8871 (1) Å	T = 293 K
c = 15.9300 (2) Å	0.30 × 0.20 × 0.20 mm
V = 4020.7 (6) Å³

Data collection top

Agilent Xcalibur (Eos, Gemini) diffractometer	1775 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	1153 reflections with I > 2σ(I)
T_min = 0.447, T_max = 0.567	R_int = 0.055
6063 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	450 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.06	Δρ_max = 0.42 e Å⁻³
1775 reflections	Δρ_min = −0.54 e Å⁻³
155 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
I1	0.61704 (3)	0.35482 (3)	0.43754 (3)	0.0704 (2)
N1	0.7883 (3)	0.4465 (3)	0.5004 (3)	0.0465 (12)
H1	0.7771	0.4175	0.5446	0.056*
O1	0.8853 (3)	0.4661 (3)	0.3977 (2)	0.0627 (13)
F1	0.9082 (8)	0.3600 (9)	0.5849 (6)	0.095 (4)	0.615 (14)
F2	0.9342 (9)	0.3088 (7)	0.4454 (6)	0.098 (4)	0.615 (14)
F3	0.9903 (8)	0.4012 (8)	0.5219 (9)	0.109 (4)	0.615 (14)
F1'	0.8791 (11)	0.3219 (12)	0.5583 (13)	0.081 (5)	0.385 (14)
F2'	0.8837 (13)	0.2878 (9)	0.4878 (15)	0.099 (5)	0.385 (14)
F3'	0.9922 (12)	0.3650 (14)	0.4827 (12)	0.091 (5)	0.385 (14)
C1	0.6481 (4)	0.4831 (4)	0.4479 (3)	0.0468 (15)
C2	0.5885 (4)	0.5432 (4)	0.4246 (4)	0.0594 (18)
H2	0.5342	0.5272	0.4099	0.071*
C3	0.6121 (5)	0.6273 (4)	0.4237 (4)	0.0649 (19)
H3	0.5728	0.6682	0.4094	0.078*
C4	0.6921 (5)	0.6507 (5)	0.4434 (4)	0.0634 (18)
H4	0.7076	0.7071	0.4400	0.076*
C5	0.7503 (4)	0.5913 (4)	0.4685 (4)	0.0543 (16)
H5	0.8045	0.6079	0.4830	0.065*
C6	0.7280 (4)	0.5074 (4)	0.4720 (3)	0.0440 (14)
C7	0.8600 (4)	0.4334 (4)	0.4613 (3)	0.0431 (14)
C8	0.9161 (5)	0.3650 (5)	0.5022 (5)	0.0577 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0683 (4)	0.0521 (4)	0.0909 (4)	−0.0005 (2)	−0.0240 (3)	0.0036 (3)
N1	0.052 (3)	0.047 (3)	0.041 (2)	0.010 (2)	−0.001 (2)	0.008 (2)
O1	0.055 (3)	0.086 (4)	0.047 (2)	0.011 (3)	0.007 (2)	0.018 (2)
F1	0.112 (8)	0.113 (8)	0.061 (5)	0.062 (6)	−0.008 (5)	0.010 (5)
F2	0.129 (8)	0.082 (6)	0.083 (5)	0.057 (6)	−0.001 (6)	−0.014 (5)
F3	0.077 (6)	0.118 (8)	0.133 (8)	0.006 (6)	−0.065 (6)	0.013 (6)
F1'	0.084 (9)	0.087 (10)	0.073 (9)	0.015 (7)	0.017 (7)	0.041 (8)
F2'	0.112 (10)	0.066 (8)	0.118 (10)	0.016 (7)	−0.039 (9)	0.003 (8)
F3'	0.063 (8)	0.116 (11)	0.092 (9)	0.036 (8)	0.018 (8)	0.027 (8)
C1	0.055 (4)	0.040 (3)	0.045 (3)	0.008 (3)	0.002 (3)	−0.001 (3)
C2	0.055 (4)	0.058 (4)	0.065 (4)	0.022 (3)	−0.007 (3)	−0.001 (3)
C3	0.080 (5)	0.046 (4)	0.069 (4)	0.026 (4)	−0.007 (4)	0.005 (3)
C4	0.078 (5)	0.045 (4)	0.067 (4)	0.013 (4)	0.004 (4)	−0.001 (3)
C5	0.066 (4)	0.048 (4)	0.049 (3)	0.003 (3)	0.004 (3)	−0.001 (3)
C6	0.053 (4)	0.042 (3)	0.037 (3)	0.014 (3)	0.006 (3)	0.004 (3)
C7	0.047 (4)	0.045 (4)	0.037 (3)	0.000 (3)	−0.005 (3)	−0.005 (3)
C8	0.052 (4)	0.062 (5)	0.059 (4)	0.015 (4)	−0.002 (4)	−0.004 (4)

Geometric parameters (Å, º) top

I1—C1	2.103 (6)	C1—C6	1.382 (8)
N1—C7	1.316 (7)	C1—C2	1.394 (8)
N1—C6	1.433 (7)	C2—C3	1.389 (9)
N1—H1	0.8600	C2—H2	0.9300
O1—C7	1.208 (6)	C3—C4	1.361 (9)
F1—C8	1.326 (12)	C3—H3	0.9300
F2—C8	1.303 (11)	C4—C5	1.380 (9)
F3—C8	1.349 (13)	C4—H4	0.9300
F1'—C8	1.271 (16)	C5—C6	1.381 (8)
F2'—C8	1.351 (16)	C5—H5	0.9300
F3'—C8	1.248 (18)	C7—C8	1.548 (9)

C7—N1—C6	122.5 (5)	C5—C6—C1	119.6 (6)
C7—N1—H1	118.8	C5—C6—N1	119.6 (6)
C6—N1—H1	118.8	C1—C6—N1	120.8 (6)
C6—C1—C2	120.4 (6)	O1—C7—N1	128.1 (6)
C6—C1—I1	120.5 (4)	O1—C7—C8	117.6 (6)
C2—C1—I1	118.9 (5)	N1—C7—C8	114.3 (6)
C3—C2—C1	118.6 (7)	F3'—C8—F1'	128.5 (12)
C3—C2—H2	120.7	F2—C8—F1	132.0 (10)
C1—C2—H2	120.7	F2—C8—F3	105.1 (10)
C4—C3—C2	120.8 (7)	F1—C8—F3	82.9 (11)
C4—C3—H3	119.6	F3'—C8—F2'	109.1 (13)
C2—C3—H3	119.6	F1'—C8—F2'	56.9 (16)
C3—C4—C5	120.4 (7)	F3'—C8—C7	116.9 (10)
C3—C4—H4	119.8	F1'—C8—C7	114.1 (9)
C5—C4—H4	119.8	F2—C8—C7	108.4 (6)
C4—C5—C6	120.0 (7)	F1—C8—C7	113.9 (7)
C4—C5—H5	120.0	F3—C8—C7	107.6 (8)
C6—C5—H5	120.0	F2'—C8—C7	110.3 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.08	2.917 (6)	163

Symmetry code: (i) y+1/4, −x+5/4, z+1/4.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.08	2.917 (6)	163

Symmetry code: (i) y+1/4, −x+5/4, z+1/4.

Acknowledgements

This work was supported by the Science Fund of the Education Office of Jiangxi (GJJ12583) and the Bureau of Science and Technology of Nanchang City.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Jeschke, P. (2004). Chembiochem, 5, 570–589. Web of Science CrossRef CAS Google Scholar
Konfink, C. C., Blank, B., Pagano, B., Gotz, N. & Knochel, P. (2007). Chem. Commun. 19, 1954–1956. Google Scholar
Mueller, K., Faeh, C. & Diederich, F. (2007). Science, 317, 1881–1886. Web of Science CrossRef PubMed CAS Google Scholar
Purser, S., Moore, P. R., Swallow, S. & Gouverneur, V. (2008). Chem. Soc. Rev. 37, 320–330. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar