N-{[2,5-Dichloro-4-(1,1,2,3,3,3-hexa­fluoro­prop­oxy)phen­yl]amino­carbon­yl}-2,6-difluoro­benzamide

Liu, Y.; Li, F.; Li, Y.

doi:10.1107/S1600536808025506

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1756

doi:10.1107/S1600536808025506

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N-{[2,5-Dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]aminocarbonyl}-2,6-difluorobenzamide

Yin-hong Liu,^a Fang-shi Li ^a ^* and Yi Li ^a

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Xinmofan Road No. 5, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: fangshi.li@njut.edu.cn

(Received 6 August 2008; accepted 8 August 2008; online 13 August 2008)

In the molecule of the title compound, C₁₇H₈Cl₂F₈N₂O₃, the two aromatic rings are oriented at a dihedral angle of 50.12 (3)°. Intramolecular N—H⋯O, C—H⋯O and N—H⋯Cl hydrogen bonds result in the formation of two six- and one five-membered rings. The six-membered rings have flattened-boat conformations, while the five-membered ring adopts an envelope conformation. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers.

Related literature

For related literature, see: Drabek & Boeger (1986 ). For bond-length data, see: Allen et al. (1987 ). For ring conformation puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₇H₈Cl₂F₈N₂O₃
M_r = 511.15
Monoclinic, P 2₁ /n
a = 9.2300 (18) Å
b = 16.404 (3) Å
c = 14.074 (3) Å
β = 108.77 (3)°
V = 2017.6 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 294 (2) K
0.40 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.851, T_max = 0.921
3609 measured reflections
3609 independent reflections
1922 reflections with I > 2σ(I)
3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.086
wR(F²) = 0.247
S = 1.09
3609 reflections
283 parameters
96 restraints
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯Cl2	0.86	2.43	2.892 (4)	115
N2—H2A⋯O1	0.86	1.98	2.664 (6)	135
N1—H1A⋯O2ⁱ	0.86	1.98	2.814 (6)	163
C10—H10A⋯O2	0.93	2.28	2.851 (6)	119
Symmetry code: (i) -x+1, -y+2, -z+1.

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: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808025506/hk2510sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808025506/hk2510Isup2.hkl

checkCIF report

Comment top

The title compound is considered to belong to the fourth generation of insectides with properties such as high selectivity, low acute toxicity for mammals and high biological activity. It is generally recognized as a chitin-synthesis inhibitor that interrupts chitin-synthesis during the development and reproduction of the insectide. As part of our studies in this area, we report herein the crystal structure of the title compound.

In the molecule of the title compound, (Fig. 1) the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6) and B (C9-C14) are, of course, planar, and the dihedral angle between them is A/B = 50.12 (3)°. The intramolecular N-H···O, C-H···O and N-H···Cl hydrogen bonds (Table 1) result in the formation of two six- and one five-membered non-planar rings: C (O1/N1/N2/C7/C8/H2A), D (O2/N2/C8-C10/H10A) and E (Cl2/N2/C9/C14/H2A). Rings C and D adopt twisted [ϕ = -169.19 (2)°, θ = 21.09 (3)° (for ring C) and ϕ = 178.48 (3)°, θ = 127.74 (3)° (for ring D)] conformations, having total puckering amplitudes, Q_T, of 0.113 (3) and 0.201 (3) Å, respectively (Cremer & Pople, 1975). Ring E adopts envelope conformation, with H2A atom displaced by 0.190 (3) Å from the plane of the other ring atoms.

In the crystal structure, intermolecular N-H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For related literature, see: Drabek & Boeger (1986). For bond-length data, see: Allen et al. (1987). For ring conformation puckering parameters, see: Cremer & Pople (1975).

Experimental top

The title compound was prepared according to the literature method (Drabek & Boeger, 1986). The crystals suitable for X-ray analysis were obtained by dissolving the title compound (0.3 g) in acetonitrile (25 ml) and evaporating the solvent slowly at room temperature for about 8 d.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. A packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

N-{[2,5-Dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]aminocarbonyl}- 2,6-difluorobenzamide top

Crystal data top

C₁₇H₈Cl₂F₈N₂O₃	F(000) = 1016
M_r = 511.15	D_x = 1.683 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 9.2300 (18) Å	θ = 9–12°
b = 16.404 (3) Å	µ = 0.42 mm⁻¹
c = 14.074 (3) Å	T = 294 K
β = 108.77 (3)°	Block, colorless
V = 2017.6 (8) Å³	0.40 × 0.30 × 0.20 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1922 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 25.2°, θ_min = 2.0°
ω/2θ scans	h = −11→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→19
T_min = 0.851, T_max = 0.921	l = 0→16
3609 measured reflections	3 standard reflections every 200 reflections
3609 independent reflections	intensity decay: none

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)] = 0.086	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.248	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.1258P)² + 1.1819P] where P = (F_o² + 2F_c²)/3
3609 reflections	(Δ/σ)_max = 0.001
283 parameters	Δρ_max = 0.42 e Å⁻³
96 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₇H₈Cl₂F₈N₂O₃	V = 2017.6 (8) Å³
M_r = 511.15	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.2300 (18) Å	µ = 0.42 mm⁻¹
b = 16.404 (3) Å	T = 294 K
c = 14.074 (3) Å	0.40 × 0.30 × 0.20 mm
β = 108.77 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1922 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.000
T_min = 0.851, T_max = 0.921	3 standard reflections every 200 reflections
3609 measured reflections	intensity decay: none
3609 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.086	96 restraints
wR(F²) = 0.248	H-atom parameters constrained
S = 1.09	Δρ_max = 0.42 e Å⁻³
3609 reflections	Δρ_min = −0.35 e Å⁻³
283 parameters

Special details top

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 > 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
Cl1	1.21022 (15)	1.15534 (9)	0.61828 (12)	0.0527 (5)
Cl2	1.06547 (19)	0.83402 (11)	0.80001 (17)	0.0914 (8)
F1	0.4001 (5)	0.7889 (3)	0.7184 (3)	0.0975 (16)
F2	0.4224 (4)	0.8023 (3)	0.3906 (3)	0.0810 (13)
F3	1.5260 (5)	1.0359 (3)	0.6887 (5)	0.1116 (18)
F4	1.5722 (4)	0.9618 (3)	0.8001 (4)	0.1039 (17)
F5	1.8146 (6)	1.0579 (3)	0.7942 (5)	0.145 (3)
F6	1.8127 (6)	1.0156 (3)	0.9703 (4)	0.1121 (18)
F7	1.9281 (6)	1.1152 (3)	0.9350 (4)	0.119 (2)
F8	1.6616 (6)	1.1347 (3)	0.9601 (4)	0.1029 (15)
O1	0.6850 (4)	0.7921 (2)	0.6546 (4)	0.0703 (15)
O2	0.6981 (4)	1.0216 (3)	0.5376 (3)	0.0505 (11)
O3	1.4248 (4)	1.0694 (3)	0.7916 (4)	0.0758 (16)
N1	0.5870 (4)	0.9045 (2)	0.5577 (3)	0.0359 (11)
H1A	0.5033	0.9242	0.5175	0.043*
N2	0.8483 (4)	0.9219 (2)	0.6377 (3)	0.0327 (10)
H2A	0.8468	0.8724	0.6576	0.039*
C1	0.1954 (8)	0.7296 (5)	0.5816 (6)	0.074 (2)
H1B	0.1414	0.7140	0.6242	0.089*
C2	0.1405 (7)	0.7183 (4)	0.4832 (5)	0.0588 (17)
H2B	0.0444	0.6945	0.4569	0.071*
C3	0.2142 (7)	0.7389 (4)	0.4199 (5)	0.0607 (17)
H3A	0.1704	0.7275	0.3519	0.073*
C4	0.3505 (6)	0.7758 (4)	0.4526 (4)	0.0450 (14)
C5	0.4228 (6)	0.7893 (3)	0.5551 (4)	0.0435 (14)
C6	0.3397 (7)	0.7666 (4)	0.6175 (5)	0.0568 (16)
C7	0.5790 (6)	0.8247 (3)	0.5960 (4)	0.0437 (14)
C8	0.7151 (6)	0.9534 (3)	0.5785 (4)	0.0407 (14)
C9	0.9852 (5)	0.9614 (3)	0.6689 (4)	0.0330 (12)
C10	1.0214 (5)	1.0332 (3)	0.6291 (4)	0.0368 (12)
H10A	0.9477	1.0595	0.5770	0.044*
C11	1.1661 (5)	1.0655 (3)	0.6667 (4)	0.0355 (12)
C12	1.2807 (6)	1.0310 (4)	0.7494 (5)	0.0518 (16)
C13	1.2445 (7)	0.9591 (4)	0.7901 (5)	0.0572 (17)
H13A	1.3159	0.9350	0.8453	0.069*
C14	1.1065 (5)	0.9252 (3)	0.7492 (4)	0.0391 (13)
C15	1.5460 (7)	1.0386 (4)	0.8024 (7)	0.079 (3)
C16	1.6854 (8)	1.0845 (5)	0.8271 (9)	0.107 (4)
H16A	1.6576	1.1394	0.7999	0.129*
C17	1.7772 (11)	1.0946 (6)	0.9319 (7)	0.089

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0401 (8)	0.0436 (9)	0.0782 (11)	−0.0152 (6)	0.0242 (7)	−0.0007 (7)
Cl2	0.0513 (10)	0.0599 (12)	0.1330 (18)	−0.0100 (8)	−0.0123 (10)	0.0497 (12)
F1	0.097 (3)	0.135 (4)	0.051 (3)	−0.054 (3)	0.010 (2)	0.026 (2)
F2	0.086 (3)	0.103 (3)	0.059 (3)	−0.045 (3)	0.030 (2)	−0.034 (2)
F3	0.099 (4)	0.106 (4)	0.133 (5)	−0.034 (3)	0.041 (3)	−0.032 (3)
F4	0.054 (2)	0.072 (3)	0.172 (5)	−0.010 (2)	0.019 (3)	−0.015 (3)
F5	0.092 (3)	0.141 (5)	0.225 (7)	−0.023 (3)	0.082 (4)	−0.111 (5)
F6	0.127 (4)	0.104 (4)	0.095 (4)	−0.017 (3)	0.021 (3)	0.052 (3)
F7	0.099 (3)	0.083 (3)	0.116 (4)	−0.024 (3)	−0.048 (3)	0.006 (3)
F8	0.097 (3)	0.111 (4)	0.103 (4)	−0.001 (3)	0.034 (3)	−0.012 (3)
O1	0.029 (2)	0.047 (3)	0.107 (4)	0.0006 (18)	−0.017 (2)	0.037 (2)
O2	0.046 (2)	0.047 (3)	0.057 (3)	−0.0033 (19)	0.013 (2)	−0.005 (2)
O3	0.035 (2)	0.043 (3)	0.129 (5)	−0.009 (2)	−0.001 (2)	0.009 (3)
N1	0.028 (2)	0.019 (2)	0.058 (3)	0.0007 (17)	0.009 (2)	0.0093 (19)
N2	0.028 (2)	0.025 (2)	0.043 (3)	−0.0005 (17)	0.0085 (19)	−0.0044 (19)
C1	0.070 (4)	0.082 (5)	0.076 (4)	−0.028 (4)	0.032 (4)	0.017 (4)
C2	0.046 (3)	0.051 (4)	0.071 (4)	−0.016 (3)	0.007 (3)	0.003 (3)
C3	0.059 (4)	0.061 (4)	0.051 (4)	−0.023 (3)	0.002 (3)	−0.014 (3)
C4	0.045 (3)	0.046 (3)	0.042 (3)	−0.003 (3)	0.011 (3)	−0.004 (3)
C5	0.039 (3)	0.042 (3)	0.047 (3)	−0.006 (2)	0.011 (2)	0.010 (3)
C6	0.044 (3)	0.067 (4)	0.053 (4)	−0.009 (3)	0.007 (3)	0.014 (3)
C7	0.045 (3)	0.039 (3)	0.047 (4)	−0.010 (3)	0.016 (3)	0.004 (3)
C8	0.037 (3)	0.027 (3)	0.051 (4)	0.000 (2)	0.005 (3)	0.009 (3)
C9	0.026 (2)	0.036 (3)	0.036 (3)	0.000 (2)	0.009 (2)	−0.005 (2)
C10	0.032 (2)	0.040 (3)	0.042 (3)	−0.007 (2)	0.016 (2)	−0.003 (2)
C11	0.033 (3)	0.035 (3)	0.044 (3)	−0.009 (2)	0.020 (2)	0.008 (2)
C12	0.030 (3)	0.053 (4)	0.065 (4)	−0.003 (2)	0.006 (3)	0.004 (3)
C13	0.042 (3)	0.051 (4)	0.071 (4)	0.013 (3)	0.007 (3)	0.017 (3)
C14	0.022 (2)	0.042 (3)	0.049 (3)	0.012 (2)	0.005 (2)	0.009 (2)
C15	0.029 (3)	0.050 (5)	0.142 (8)	0.006 (3)	0.007 (4)	−0.014 (4)
C16	0.041 (4)	0.046 (4)	0.219 (11)	−0.009 (3)	0.021 (5)	0.007 (6)
C17	0.080	0.089	0.096	−0.006	0.026	0.004

Geometric parameters (Å, º) top

Cl1—C11	1.727 (5)	C2—C3	1.326 (9)
Cl2—C14	1.751 (6)	C2—H2B	0.9300
F1—C6	1.398 (7)	O3—C15	1.191 (7)
F2—C4	1.327 (7)	O3—C12	1.418 (6)
F3—C15	1.552 (10)	C3—C4	1.338 (8)
F4—C15	1.284 (8)	C3—H3A	0.9300
F5—C16	1.477 (9)	C4—C5	1.399 (8)
F6—C17	1.403 (10)	C5—C6	1.389 (8)
F7—C17	1.420 (10)	C5—C7	1.488 (7)
F8—C17	1.415 (10)	C9—C10	1.390 (7)
O1—C7	1.186 (6)	C9—C14	1.439 (7)
N1—C8	1.380 (6)	C10—C11	1.374 (7)
N1—C7	1.427 (7)	C10—H10A	0.9300
N1—H1A	0.8600	C11—C12	1.414 (7)
C1—C2	1.327 (10)	C12—C13	1.398 (8)
C1—C6	1.401 (9)	C13—C14	1.338 (8)
C1—H1B	0.9300	C13—H13A	0.9300
N2—C8	1.347 (6)	C15—C16	1.434 (9)
N2—C9	1.361 (6)	C16—C17	1.455 (13)
N2—H2A	0.8600	C16—H16A	0.9800
O2—C8	1.245 (6)

C8—N1—C7	126.7 (4)	C11—C10—C9	120.1 (5)
C8—N1—H1A	116.6	C11—C10—H10A	120.0
C7—N1—H1A	116.6	C9—C10—H10A	120.0
C2—C1—C6	115.8 (6)	C10—C11—C12	122.7 (5)
C2—C1—H1B	122.1	C10—C11—Cl1	120.0 (4)
C6—C1—H1B	122.1	C12—C11—Cl1	117.2 (4)
C8—N2—C9	125.8 (4)	C13—C12—C11	117.4 (5)
C8—N2—H2A	117.1	C13—C12—O3	121.2 (5)
C9—N2—H2A	117.1	C11—C12—O3	121.4 (5)
C1—C2—C3	124.0 (6)	C14—C13—C12	119.7 (5)
C1—C2—H2B	118.0	C14—C13—H13A	120.2
C3—C2—H2B	118.0	C12—C13—H13A	120.2
C15—O3—C12	125.5 (6)	C13—C14—C9	123.9 (5)
C2—C3—C4	120.9 (6)	C13—C14—Cl2	118.8 (4)
C2—C3—H3A	119.6	C9—C14—Cl2	117.2 (4)
C4—C3—H3A	119.6	O3—C15—F4	126.1 (6)
F2—C4—C3	122.4 (6)	O3—C15—C16	122.7 (7)
F2—C4—C5	117.0 (5)	F4—C15—C16	111.1 (6)
C3—C4—C5	120.7 (6)	O3—C15—F3	94.9 (6)
C6—C5—C4	115.6 (5)	F4—C15—F3	84.7 (6)
C6—C5—C7	121.6 (5)	C16—C15—F3	93.7 (7)
C4—C5—C7	122.8 (5)	C15—C16—C17	119.4 (9)
C5—C6—F1	116.8 (5)	C15—C16—F5	121.4 (7)
C5—C6—C1	122.9 (6)	C17—C16—F5	94.9 (6)
F1—C6—C1	120.1 (6)	C15—C16—H16A	106.6
O1—C7—N1	123.1 (5)	C17—C16—H16A	106.6
O1—C7—C5	125.0 (5)	F5—C16—H16A	106.6
N1—C7—C5	111.9 (5)	F6—C17—F8	115.2 (7)
O2—C8—N2	125.8 (5)	F6—C17—F7	95.9 (6)
O2—C8—N1	116.9 (4)	F8—C17—F7	134.6 (8)
N2—C8—N1	117.2 (5)	F6—C17—C16	105.8 (7)
N2—C9—C10	126.3 (5)	F8—C17—C16	95.3 (7)
N2—C9—C14	117.6 (5)	F7—C17—C16	107.7 (7)
C10—C9—C14	116.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl2	0.86	2.43	2.892 (4)	115
N2—H2A···O1	0.86	1.98	2.664 (6)	135
N1—H1A···O2ⁱ	0.86	1.98	2.814 (6)	163
C10—H10A···O2	0.93	2.28	2.851 (6)	119

Symmetry code: (i) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₈Cl₂F₈N₂O₃
M_r	511.15
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	9.2300 (18), 16.404 (3), 14.074 (3)
β (°)	108.77 (3)
V (Å³)	2017.6 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.851, 0.921
No. of measured, independent and observed [I > 2σ(I)] reflections	3609, 3609, 1922
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.598

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.086, 0.248, 1.09
No. of reflections	3609
No. of parameters	283
No. of restraints	96
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.35

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl2	0.86	2.43	2.892 (4)	114.7
N2—H2A···O1	0.86	1.98	2.664 (6)	135.4
N1—H1A···O2ⁱ	0.86	1.98	2.814 (6)	163.2
C10—H10A···O2	0.93	2.28	2.851 (6)	119.0

Symmetry code: (i) −x+1, −y+2, −z+1.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Drabek, J. & Boeger, M. (1986). European Patent No. 179022. Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 9| September 2008| Page o1756

doi:10.1107/S1600536808025506

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N-{[2,5-Di­chloro-4-(1,1,2,3,3,3-hexa­fluoro­prop­­oxy)phen­yl]amino­carbon­yl}-2,6-di­fluoro­benzamide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

N-{[2,5-Dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]aminocarbonyl}-2,6-difluorobenzamide