N-[3,5-Dichloro-4-(1,1,2,2-tetra-fluoro-eth-oxy)phen-yl]-2,6-difluoro-benzamide.

In the title compound, C(15)H(7)Cl(2)F(6)NO(2), the conformation of the N-H bond in the amide segment is anti to the C=O bond and the dihedral angle between the two benzene rings is 78.6 (3)°. The terminal -CHF(2) group is disordered over two orientations in a 0.67:0.33 ratio. In the crystal, the mol-ecules are linked by N-H⋯O hydrogen bonds, generating C(4) chains propagating in [100].

Related literature

For background to the biological properties of related compounds, see: Liu, Li & Li (2004 ▶); Liu, Li & Zhong (2004 ▶); Shiga et al. (2003 ▶). For a related structure, see: Gowda et al. (2010 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H7Cl2F6NO2

M = 418.12

Orthorhombic,

a = 9.426 (2) Å

b = 15.568 (4) Å

c = 22.601 (6) Å

V = 3316.7 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.47 mm−1

T = 298 K

0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.929, T max = 0.955

16415 measured reflections

2916 independent reflections

2111 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.084

wR(F 2) = 0.253

S = 1.06

2916 reflections

254 parameters

35 restraints

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.41 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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 datablocks global, I. DOI: 10.1107/S1600536810029612/hb5568sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029612/hb5568Isup2.hkl

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

C15H7Cl2F6NO2	Dx = 1.675 Mg m−3
Mr = 418.12	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 3100 reflections
a = 9.426 (2) Å	θ = 2.7–20.5°
b = 15.568 (4) Å	µ = 0.47 mm−1
c = 22.601 (6) Å	T = 298 K
V = 3316.7 (15) Å3	Block, colorless
Z = 8	0.16 × 0.12 × 0.10 mm
F(000) = 1664

Bruker SMART APEX CCD diffractometer	2916 independent reflections
Radiation source: fine-focus sealed tube	2111 reflections with I > 2σ(I)
graphite	Rint = 0.075
φ and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
Tmin = 0.929, Tmax = 0.955	k = −16→18
16415 measured reflections	l = −26→24

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)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.253	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.1378P)2 + 2.4511P] where P = (Fo2 + 2Fc2)/3
2916 reflections	(Δ/σ)max = 0.001
254 parameters	Δρmax = 0.54 e Å−3
35 restraints	Δρmin = −0.40 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	Occ. (<1)
C1	0.2885 (5)	0.6858 (3)	0.5451 (2)	0.0619 (12)
C2	0.2068 (8)	0.6985 (5)	0.5949 (3)	0.096 (2)
C3	0.1779 (10)	0.6367 (8)	0.6345 (4)	0.143 (4)
H3	0.1250	0.6481	0.6684	0.172*
C4	0.2302 (11)	0.5553 (7)	0.6230 (4)	0.132 (4)
H4	0.2102	0.5110	0.6493	0.158*
C5	0.3106 (8)	0.5382 (4)	0.5739 (4)	0.103 (2)
H5	0.3445	0.4831	0.5665	0.124*
C6	0.3391 (6)	0.6032 (4)	0.5365 (3)	0.0741 (15)
C7	0.3282 (4)	0.7581 (3)	0.5045 (2)	0.0564 (11)
C8	0.2294 (4)	0.8573 (3)	0.4316 (2)	0.0559 (11)
C9	0.1389 (5)	0.8554 (3)	0.3827 (2)	0.0613 (12)
H9	0.0775	0.8093	0.3773	0.074*
C10	0.1405 (5)	0.9217 (3)	0.3424 (2)	0.0636 (12)
C11	0.2300 (6)	0.9916 (3)	0.3497 (2)	0.0672 (13)
C12	0.3205 (5)	0.9913 (3)	0.3980 (3)	0.0701 (14)
C13	0.3201 (5)	0.9259 (3)	0.4389 (3)	0.0683 (14)
H13	0.3807	0.9280	0.4714	0.082*
C14	0.1507 (7)	1.1246 (4)	0.3126 (3)	0.0855 (17)
C15	0.1869 (11)	1.1839 (5)	0.2601 (4)	0.146 (3)
H15	0.2893	1.1945	0.2585	0.175*	0.67
H15'	0.2111	1.1413	0.2298	0.175*	0.33
Cl1	0.43376 (19)	1.07768 (10)	0.40998 (10)	0.1141 (8)
Cl2	0.0311 (2)	0.91643 (11)	0.28089 (7)	0.1026 (7)
F1	0.1596 (6)	0.7801 (4)	0.6046 (2)	0.1471 (19)
F2	0.4199 (4)	0.5898 (2)	0.48811 (18)	0.1020 (12)
F3	0.0163 (5)	1.1038 (3)	0.3168 (3)	0.1456 (19)
F4	0.1720 (6)	1.1679 (3)	0.3624 (2)	0.1382 (18)
N1	0.2209 (4)	0.7900 (2)	0.47228 (18)	0.0605 (10)
H1	0.1390	0.7667	0.4771	0.073*
O1	0.4498 (3)	0.7837 (2)	0.5020 (2)	0.0816 (11)
O2	0.2375 (4)	1.0559 (2)	0.30668 (17)	0.0788 (11)
F6	0.1153 (11)	1.2577 (5)	0.2708 (4)	0.163 (3)	0.67
F5	0.1452 (10)	1.1438 (6)	0.2108 (4)	0.161 (3)	0.67
F5'	0.3088 (15)	1.2237 (11)	0.2688 (8)	0.157 (6)	0.33
F6'	0.0536 (18)	1.2059 (19)	0.2406 (12)	0.219 (10)	0.33

	U11	U22	U33	U12	U13	U23
C1	0.051 (3)	0.069 (3)	0.066 (3)	−0.002 (2)	−0.004 (2)	0.006 (2)
C2	0.095 (4)	0.118 (6)	0.073 (4)	0.010 (4)	0.008 (3)	0.010 (4)
C3	0.139 (7)	0.207 (11)	0.084 (5)	−0.018 (8)	0.013 (5)	0.049 (7)
C4	0.142 (8)	0.139 (7)	0.115 (7)	−0.049 (6)	−0.032 (6)	0.069 (6)
C5	0.122 (6)	0.076 (4)	0.112 (6)	−0.022 (4)	−0.030 (5)	0.038 (4)
C6	0.075 (3)	0.065 (3)	0.082 (4)	−0.007 (3)	−0.013 (3)	0.011 (3)
C7	0.048 (2)	0.048 (2)	0.074 (3)	0.006 (2)	0.002 (2)	−0.003 (2)
C8	0.043 (2)	0.048 (2)	0.076 (3)	0.0048 (18)	0.007 (2)	0.000 (2)
C9	0.063 (3)	0.051 (3)	0.069 (3)	−0.005 (2)	0.010 (2)	−0.008 (2)
C10	0.072 (3)	0.061 (3)	0.058 (3)	0.003 (2)	0.009 (2)	−0.012 (2)
C11	0.071 (3)	0.053 (3)	0.077 (3)	0.007 (2)	0.015 (3)	−0.001 (2)
C12	0.058 (3)	0.046 (3)	0.105 (4)	0.002 (2)	0.001 (3)	0.008 (2)
C13	0.059 (3)	0.046 (3)	0.100 (4)	0.006 (2)	−0.015 (3)	0.000 (2)
C14	0.105 (5)	0.058 (3)	0.093 (4)	0.006 (3)	−0.008 (3)	0.002 (3)
C15	0.155 (5)	0.127 (5)	0.154 (5)	0.027 (4)	−0.017 (4)	0.016 (4)
Cl1	0.0934 (12)	0.0600 (9)	0.189 (2)	−0.0223 (7)	−0.0398 (12)	0.0268 (10)
Cl2	0.1460 (16)	0.0985 (12)	0.0632 (9)	−0.0185 (10)	−0.0191 (9)	−0.0054 (7)
F1	0.174 (5)	0.159 (4)	0.109 (3)	0.050 (4)	0.041 (3)	−0.021 (3)
F2	0.123 (3)	0.067 (2)	0.116 (3)	0.0233 (19)	0.022 (2)	0.0026 (18)
F3	0.097 (3)	0.097 (3)	0.243 (6)	0.021 (2)	0.027 (3)	0.002 (3)
F4	0.186 (5)	0.104 (3)	0.125 (3)	0.062 (3)	−0.023 (3)	−0.016 (3)
N1	0.042 (2)	0.055 (2)	0.084 (3)	−0.0037 (16)	0.0022 (18)	0.0098 (19)
O1	0.0474 (19)	0.064 (2)	0.134 (3)	−0.0028 (16)	−0.014 (2)	0.020 (2)
O2	0.091 (3)	0.059 (2)	0.086 (3)	0.0114 (18)	0.022 (2)	0.0166 (18)
F6	0.179 (5)	0.136 (4)	0.174 (5)	0.032 (4)	−0.008 (4)	0.038 (4)
F5	0.189 (5)	0.165 (5)	0.129 (4)	0.017 (4)	−0.020 (4)	0.012 (4)
F5'	0.157 (7)	0.154 (7)	0.160 (7)	−0.004 (5)	0.007 (5)	0.006 (5)
F6'	0.217 (11)	0.221 (11)	0.218 (11)	0.004 (5)	−0.006 (5)	0.005 (5)

C1—C2	1.377 (8)	C10—Cl2	1.733 (5)
C1—C6	1.385 (7)	C11—C12	1.385 (7)
C1—C7	1.500 (7)	C11—O2	1.398 (6)
C2—C3	1.344 (11)	C12—C13	1.375 (7)
C2—F1	1.363 (8)	C12—Cl1	1.738 (5)
C3—C4	1.384 (13)	C13—H13	0.9300
C3—H3	0.9300	C14—F3	1.311 (8)
C4—C5	1.370 (13)	C14—F4	1.328 (7)
C4—H4	0.9300	C14—O2	1.352 (7)
C5—C6	1.346 (8)	C14—C15	1.540 (8)
C5—H5	0.9300	C15—F5'	1.321 (10)
C6—F2	1.350 (7)	C15—F5	1.335 (8)
C7—O1	1.215 (5)	C15—F6	1.355 (8)
C7—N1	1.341 (6)	C15—F6'	1.375 (10)
C8—C13	1.379 (6)	C15—H15	0.9800
C8—N1	1.395 (6)	C15—H15'	0.9791
C8—C9	1.398 (7)	N1—H1	0.8600
C9—C10	1.375 (7)	F5—H15'	0.7554
C9—H9	0.9300	F5'—H15	0.5415
C10—C11	1.388 (7)
C2—C1—C6	116.1 (5)	C12—C13—C8	119.7 (5)
C2—C1—C7	122.1 (5)	C12—C13—H13	120.2
C6—C1—C7	121.6 (5)	C8—C13—H13	120.2
C3—C2—F1	119.6 (8)	F3—C14—F4	102.1 (6)
C3—C2—C1	123.7 (8)	F3—C14—O2	113.3 (5)
F1—C2—C1	116.7 (6)	F4—C14—O2	113.2 (5)
C2—C3—C4	117.3 (9)	F3—C14—C15	114.7 (6)
C2—C3—H3	121.4	F4—C14—C15	108.4 (6)
C4—C3—H3	121.4	O2—C14—C15	105.3 (6)
C5—C4—C3	121.8 (7)	F5'—C15—F5	126.8 (12)
C5—C4—H4	119.1	F5'—C15—F6	90.5 (10)
C3—C4—H4	119.1	F5—C15—F6	113.5 (9)
C6—C5—C4	118.2 (8)	F5'—C15—F6'	136.5 (16)
C6—C5—H5	120.9	F5—C15—F6'	65.2 (13)
C4—C5—H5	120.9	F6—C15—F6'	52.4 (12)
C5—C6—F2	120.3 (6)	F5'—C15—C14	111.1 (10)
C5—C6—C1	122.8 (7)	F5—C15—C14	107.3 (8)
F2—C6—C1	116.8 (4)	F6—C15—C14	105.1 (7)
O1—C7—N1	124.4 (4)	F6'—C15—C14	101.2 (13)
O1—C7—C1	120.6 (4)	F5'—C15—H15	21.3
N1—C7—C1	115.0 (4)	F5—C15—H15	109.8
C13—C8—N1	122.6 (5)	F6—C15—H15	110.7
C13—C8—C9	119.3 (4)	F6'—C15—H15	147.7
N1—C8—C9	118.1 (4)	C14—C15—H15	110.3
C10—C9—C8	120.1 (4)	F5'—C15—H15'	102.6
C10—C9—H9	120.0	F5—C15—H15'	33.9
C8—C9—H9	120.0	F6—C15—H15'	144.6
C9—C10—C11	121.1 (5)	F6'—C15—H15'	99.0
C9—C10—Cl2	119.3 (4)	C14—C15—H15'	100.6
C11—C10—Cl2	119.6 (4)	H15—C15—H15'	82.0
C12—C11—C10	117.7 (5)	C7—N1—C8	126.3 (4)
C12—C11—O2	121.3 (5)	C7—N1—H1	116.9
C10—C11—O2	120.6 (5)	C8—N1—H1	116.9
C13—C12—C11	122.1 (5)	C14—O2—C11	117.9 (4)
C13—C12—Cl1	118.0 (4)	C15—F5—H15'	46.3
C11—C12—Cl1	119.9 (4)	C15—F5'—H15	41.2
C6—C1—C2—C3	1.5 (10)	C10—C11—C12—Cl1	−179.3 (4)
C7—C1—C2—C3	−174.9 (7)	O2—C11—C12—Cl1	6.7 (7)
C6—C1—C2—F1	178.3 (5)	C11—C12—C13—C8	1.4 (8)
C7—C1—C2—F1	1.9 (9)	Cl1—C12—C13—C8	178.6 (4)
F1—C2—C3—C4	−179.0 (8)	N1—C8—C13—C12	−178.3 (5)
C1—C2—C3—C4	−2.3 (13)	C9—C8—C13—C12	−0.1 (7)
C2—C3—C4—C5	1.3 (14)	F3—C14—C15—F5'	159.9 (10)
C3—C4—C5—C6	0.4 (13)	F4—C14—C15—F5'	46.6 (12)
C4—C5—C6—F2	178.8 (6)	O2—C14—C15—F5'	−74.8 (11)
C4—C5—C6—C1	−1.2 (10)	F3—C14—C15—F5	−57.7 (10)
C2—C1—C6—C5	0.4 (8)	F4—C14—C15—F5	−171.1 (7)
C7—C1—C6—C5	176.8 (5)	O2—C14—C15—F5	67.5 (9)
C2—C1—C6—F2	−179.7 (5)	F3—C14—C15—F6	63.3 (10)
C7—C1—C6—F2	−3.3 (7)	F4—C14—C15—F6	−50.0 (10)
C2—C1—C7—O1	109.9 (6)	O2—C14—C15—F6	−171.4 (8)
C6—C1—C7—O1	−66.3 (7)	F3—C14—C15—F6'	9.5 (16)
C2—C1—C7—N1	−70.5 (7)	F4—C14—C15—F6'	−103.8 (15)
C6—C1—C7—N1	113.3 (5)	O2—C14—C15—F6'	134.8 (15)
C13—C8—C9—C10	−0.2 (7)	O1—C7—N1—C8	−0.8 (8)
N1—C8—C9—C10	178.0 (4)	C1—C7—N1—C8	179.6 (4)
C8—C9—C10—C11	−0.6 (7)	C13—C8—N1—C7	−33.8 (7)
C8—C9—C10—Cl2	178.1 (4)	C9—C8—N1—C7	148.1 (5)
C9—C10—C11—C12	1.8 (7)	F3—C14—O2—C11	−55.4 (7)
Cl2—C10—C11—C12	−177.0 (4)	F4—C14—O2—C11	60.3 (7)
C9—C10—C11—O2	175.9 (4)	C15—C14—O2—C11	178.5 (6)
Cl2—C10—C11—O2	−2.9 (6)	C12—C11—O2—C14	−94.2 (6)
C10—C11—C12—C13	−2.2 (8)	C10—C11—O2—C14	92.0 (6)
O2—C11—C12—C13	−176.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.00	2.861 (5)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.00	2.861 (5)	174

Symmetry code: (i) .