N-Benzyl-2,3,4,5,6-penta-fluoro-benz-amide.

In the title compound, C(14)H(8)F(5)NO, the dihedral angle between the planes of the penta-fluoro-phenyl and phenyl rings is 18.34 (5)°. An inter-molecular N-H⋯O hydrogen bond between the amide groups connects these mol-ecules to form an infinite chain through the crystal structure. One weak intermolecular C-H⋯O contact and one π-π interaction [centroid-centroid distance = 3.772 (3) Å] are also involved in crystal structure stabilization between the phenyl rings.

Related literature

For related structures, see: An & Rhee (2003 ▶); Cockroft et al. (2007 ▶); Forbes et al. (2001 ▶); Liu et al. (2007 ▶); Qadeer et al. (2007 ▶); Zhang & Zhang (2008 ▶). For anion⋯π inter­actions, see: Albrecht et al. (2010 ▶); Lahtinen & Rissanen (2007 ▶); Müller et al. (2010 ▶).

Experimental

Crystal data

C14H8F5NO

M = 301.21

Monoclinic,

a = 7.1649 (2) Å

b = 22.9090 (5) Å

c = 7.5363 (1) Å

β = 99.205 (2)°

V = 1221.08 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 123 K

0.40 × 0.28 × 0.26 mm

Data collection

Bruker Nonius KappaCCD with APEXII detector diffractometer

4246 measured reflections

2152 independent reflections

1891 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.086

S = 1.06

2152 reflections

193 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Data collection: COLLECT (Bruker, 2008 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810043345/bt5380sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043345/bt5380Isup2.hkl

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

C14H8F5NO	F(000) = 608
Mr = 301.21	Dx = 1.638 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.1649 (2) Å	Cell parameters from 3094 reflections
b = 22.9090 (5) Å	θ = 0.4–28.3°
c = 7.5363 (1) Å	µ = 0.16 mm−1
β = 99.205 (2)°	T = 123 K
V = 1221.08 (5) Å3	Block, colourless
Z = 4	0.40 × 0.28 × 0.26 mm

Bruker Nonius KappaCCD with APEXII detector diffractometer	1891 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
graphite	θmax = 25.0°, θmin = 2.9°
Detector resolution: 9 pixels mm-1	h = −8→8
φ and ω scans	k = −27→27
4246 measured reflections	l = −8→8
2152 independent 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0393P)2 + 0.498P] where P = (Fo2 + 2Fc2)/3
2152 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 0.20 e Å−3
1 restraint	Δρmin = −0.18 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
F1	0.11992 (14)	0.19154 (4)	−0.04946 (11)	0.0315 (2)
F2	0.17000 (14)	0.07495 (4)	−0.05119 (12)	0.0350 (3)
F3	0.14683 (15)	0.01169 (4)	0.24882 (14)	0.0379 (3)
F4	0.06766 (15)	0.06526 (4)	0.54949 (12)	0.0363 (3)
F5	0.00325 (13)	0.18090 (4)	0.54897 (11)	0.0277 (2)
O1	−0.10620 (15)	0.27306 (4)	0.12572 (13)	0.0260 (3)
N8	0.12659 (19)	0.28716 (5)	0.36339 (16)	0.0232 (3)
H8	0.218 (2)	0.2705 (7)	0.437 (2)	0.028*
C1	0.1073 (2)	0.37470 (6)	0.55552 (19)	0.0207 (3)
C2	0.1399 (2)	0.43426 (7)	0.5826 (2)	0.0240 (3)
H2	0.1652	0.4579	0.4856	0.029*
C3	0.1359 (2)	0.45945 (7)	0.7488 (2)	0.0278 (4)
H3	0.1570	0.5002	0.7649	0.033*
C4	0.1011 (2)	0.42535 (7)	0.8916 (2)	0.0277 (4)
H4	0.0983	0.4425	1.0059	0.033*
C5	0.0703 (2)	0.36600 (7)	0.8668 (2)	0.0262 (4)
H5	0.0474	0.3424	0.9648	0.031*
C6	0.0729 (2)	0.34078 (7)	0.6995 (2)	0.0226 (3)
H6	0.0509	0.3001	0.6835	0.027*
C7	0.1041 (2)	0.35043 (6)	0.3685 (2)	0.0262 (4)
H7A	−0.0174	0.3612	0.2935	0.031*
H7B	0.2068	0.3689	0.3149	0.031*
C9	0.0197 (2)	0.25426 (6)	0.24216 (18)	0.0197 (3)
C10	0.0625 (2)	0.18984 (6)	0.25080 (18)	0.0197 (3)
C11	0.1035 (2)	0.16115 (7)	0.09949 (19)	0.0224 (3)
C12	0.1315 (2)	0.10168 (7)	0.0975 (2)	0.0249 (4)
C13	0.1202 (2)	0.06950 (7)	0.2499 (2)	0.0258 (4)
C14	0.0806 (2)	0.09667 (7)	0.4021 (2)	0.0253 (4)
C15	0.0511 (2)	0.15619 (7)	0.40118 (19)	0.0215 (3)

	U11	U22	U33	U12	U13	U23
F1	0.0414 (6)	0.0350 (5)	0.0190 (5)	−0.0003 (4)	0.0075 (4)	0.0023 (4)
F2	0.0382 (6)	0.0351 (5)	0.0326 (5)	0.0004 (4)	0.0089 (4)	−0.0129 (4)
F3	0.0420 (6)	0.0199 (5)	0.0515 (6)	0.0005 (4)	0.0070 (5)	−0.0003 (4)
F4	0.0463 (6)	0.0303 (5)	0.0315 (5)	−0.0016 (4)	0.0039 (4)	0.0131 (4)
F5	0.0343 (5)	0.0314 (5)	0.0176 (4)	−0.0017 (4)	0.0050 (4)	−0.0009 (4)
O1	0.0271 (6)	0.0248 (6)	0.0223 (5)	−0.0011 (5)	−0.0072 (5)	0.0037 (4)
N8	0.0258 (7)	0.0204 (7)	0.0203 (6)	0.0035 (5)	−0.0057 (5)	−0.0006 (5)
C1	0.0169 (7)	0.0222 (8)	0.0215 (7)	0.0018 (6)	−0.0015 (6)	0.0001 (6)
C2	0.0239 (8)	0.0241 (8)	0.0232 (8)	−0.0008 (6)	0.0016 (6)	0.0022 (6)
C3	0.0255 (8)	0.0233 (8)	0.0333 (9)	−0.0014 (7)	0.0006 (7)	−0.0045 (7)
C4	0.0249 (9)	0.0354 (9)	0.0227 (8)	0.0027 (7)	0.0034 (6)	−0.0067 (7)
C5	0.0217 (8)	0.0350 (9)	0.0222 (8)	0.0016 (7)	0.0046 (6)	0.0041 (6)
C6	0.0209 (8)	0.0201 (7)	0.0256 (8)	0.0005 (6)	0.0001 (6)	0.0019 (6)
C7	0.0345 (9)	0.0212 (8)	0.0212 (8)	0.0008 (7)	−0.0004 (6)	0.0009 (6)
C9	0.0191 (8)	0.0242 (8)	0.0158 (7)	−0.0019 (6)	0.0025 (6)	0.0024 (6)
C10	0.0148 (7)	0.0243 (8)	0.0186 (7)	−0.0017 (6)	−0.0020 (5)	−0.0001 (6)
C11	0.0193 (8)	0.0288 (8)	0.0184 (7)	−0.0028 (6)	0.0006 (6)	0.0028 (6)
C12	0.0188 (8)	0.0291 (8)	0.0262 (8)	−0.0014 (6)	0.0017 (6)	−0.0074 (7)
C13	0.0212 (8)	0.0192 (8)	0.0355 (9)	−0.0010 (6)	0.0000 (7)	−0.0002 (6)
C14	0.0229 (8)	0.0260 (8)	0.0256 (8)	−0.0031 (6)	−0.0002 (6)	0.0074 (6)
C15	0.0183 (8)	0.0269 (8)	0.0183 (7)	−0.0018 (6)	−0.0008 (6)	−0.0014 (6)

F1—C11	1.3419 (17)	C3—H3	0.9500
F2—C12	1.3439 (18)	C4—C5	1.385 (2)
F3—C13	1.3381 (18)	C4—H4	0.9500
F4—C14	1.3393 (17)	C5—C6	1.390 (2)
F5—C15	1.3418 (17)	C5—H5	0.9500
O1—C9	1.2313 (17)	C6—H6	0.9500
N8—C9	1.3287 (19)	C7—H7A	0.9900
N8—C7	1.4596 (19)	C7—H7B	0.9900
N8—H8	0.876 (14)	C9—C10	1.507 (2)
C1—C6	1.388 (2)	C10—C15	1.384 (2)
C1—C2	1.394 (2)	C10—C11	1.388 (2)
C1—C7	1.512 (2)	C11—C12	1.377 (2)
C2—C3	1.383 (2)	C12—C13	1.378 (2)
C2—H2	0.9500	C13—C14	1.374 (2)
C3—C4	1.385 (2)	C14—C15	1.380 (2)
C9—N8—C7	121.84 (13)	N8—C7—H7B	108.8
C9—N8—H8	118.6 (11)	C1—C7—H7B	108.8
C7—N8—H8	119.4 (11)	H7A—C7—H7B	107.7
C6—C1—C2	118.69 (14)	O1—C9—N8	124.59 (14)
C6—C1—C7	122.99 (13)	O1—C9—C10	119.63 (13)
C2—C1—C7	118.28 (13)	N8—C9—C10	115.78 (12)
C3—C2—C1	120.92 (14)	C15—C10—C11	117.21 (14)
C3—C2—H2	119.5	C15—C10—C9	122.86 (13)
C1—C2—H2	119.5	C11—C10—C9	119.79 (13)
C2—C3—C4	120.05 (14)	F1—C11—C12	118.15 (13)
C2—C3—H3	120.0	F1—C11—C10	120.00 (14)
C4—C3—H3	120.0	C12—C11—C10	121.84 (14)
C3—C4—C5	119.56 (14)	F2—C12—C11	120.61 (14)
C3—C4—H4	120.2	F2—C12—C13	119.90 (14)
C5—C4—H4	120.2	C11—C12—C13	119.49 (14)
C4—C5—C6	120.37 (14)	F3—C13—C14	120.15 (14)
C4—C5—H5	119.8	F3—C13—C12	119.81 (14)
C6—C5—H5	119.8	C14—C13—C12	120.04 (14)
C1—C6—C5	120.40 (14)	F4—C14—C13	119.99 (14)
C1—C6—H6	119.8	F4—C14—C15	120.27 (14)
C5—C6—H6	119.8	C13—C14—C15	119.73 (14)
N8—C7—C1	113.87 (12)	F5—C15—C14	118.18 (13)
N8—C7—H7A	108.8	F5—C15—C10	120.08 (13)
C1—C7—H7A	108.8	C14—C15—C10	121.69 (14)
C6—C1—C2—C3	−0.8 (2)	F1—C11—C12—F2	−1.4 (2)
C7—C1—C2—C3	177.02 (14)	C10—C11—C12—F2	179.65 (13)
C1—C2—C3—C4	0.7 (2)	F1—C11—C12—C13	178.39 (13)
C2—C3—C4—C5	0.0 (2)	C10—C11—C12—C13	−0.6 (2)
C3—C4—C5—C6	−0.5 (2)	F2—C12—C13—F3	−0.3 (2)
C2—C1—C6—C5	0.3 (2)	C11—C12—C13—F3	179.87 (14)
C7—C1—C6—C5	−177.44 (14)	F2—C12—C13—C14	−179.91 (14)
C4—C5—C6—C1	0.4 (2)	C11—C12—C13—C14	0.3 (2)
C9—N8—C7—C1	135.84 (15)	F3—C13—C14—F4	−0.3 (2)
C6—C1—C7—N8	−19.9 (2)	C12—C13—C14—F4	179.26 (13)
C2—C1—C7—N8	162.42 (14)	F3—C13—C14—C15	−179.20 (14)
C7—N8—C9—O1	−0.4 (2)	C12—C13—C14—C15	0.4 (2)
C7—N8—C9—C10	178.57 (13)	F4—C14—C15—F5	−2.2 (2)
O1—C9—C10—C15	−121.13 (16)	C13—C14—C15—F5	176.69 (13)
N8—C9—C10—C15	59.85 (19)	F4—C14—C15—C10	−179.71 (13)
O1—C9—C10—C11	54.5 (2)	C13—C14—C15—C10	−0.8 (2)
N8—C9—C10—C11	−124.55 (15)	C11—C10—C15—F5	−176.90 (12)
C15—C10—C11—F1	−178.80 (13)	C9—C10—C15—F5	−1.2 (2)
C9—C10—C11—F1	5.4 (2)	C11—C10—C15—C14	0.5 (2)
C15—C10—C11—C12	0.1 (2)	C9—C10—C15—C14	176.25 (14)
C9—C10—C11—C12	−175.70 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···O1i	0.88 (1)	2.01 (1)	2.875 (2)	171 (2)
C5—H5···O1ii	0.95	2.37	3.276 (2)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H8⋯O1i	0.88 (1)	2.01 (1)	2.875 (2)	171 (2)
C5—H5⋯O1ii	0.95	2.37	3.276 (2)	158

Symmetry codes: (i) ; (ii) .