N-{[2,5-Dichloro-4-(1,1,2,3,3,3-hexa-fluoro-prop-oxy)phen-yl]amino-carbon-yl}-2,6-difluoro-benzamide.

In the mol-ecule of the title compound, C(17)H(8)Cl(2)F(8)N(2)O(3), the two aromatic rings are oriented at a dihedral angle of 50.12 (3)°. Intra-molecular 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, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules 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 = 511.15

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.086

wR(F 2) = 0.247

S = 1.09

3609 reflections

283 parameters

96 restraints

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.34 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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

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

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

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

C17H8Cl2F8N2O3	F000 = 1016
Mr = 511.15	Dx = 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 = 9–12º
b = 16.404 (3) Å	µ = 0.42 mm−1
c = 14.074 (3) Å	T = 294 (2) K
β = 108.77 (3)º	Block, colorless
V = 2017.6 (8) Å3	0.40 × 0.30 × 0.20 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.0000
Radiation source: fine-focus sealed tube	θmax = 25.2º
Monochromator: graphite	θmin = 2.0º
T = 294(2) K	h = −11→10
ω/2θ scans	k = 0→19
Absorption correction: ψ scan(North et al., 1968)	l = 0→16
Tmin = 0.851, Tmax = 0.921	3 standard reflections
3609 measured reflections	every 200 reflections
3609 independent reflections	intensity decay: none
1922 reflections with I > 2σ(I)

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)] = 0.086	H-atom parameters constrained
wR(F2) = 0.248	w = 1/[σ2(Fo2) + (0.1258P)2 + 1.1819P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
3609 reflections	Δρmax = 0.42 e Å−3
283 parameters	Δρmin = −0.34 e Å−3
96 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
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

	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

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)

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

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) .