2,3,4,5,6-Penta­fluoro­benz­amide

The dihedral angle between the amide group and the penta­fluoro­phenyl moiety of the title compound, C₇H₂F₅ON, is 43.56 (5)°. The mol­ecules are connected via N—H...O=C bonds into an infinite, two-dimensional network generated by the cyclic (8) and chain C(4) motifs.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• R factor = 0.035
• wR factor = 0.090
• Data-to-parameter ratio = 11.2

checkCIF/PLATON results

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2000); cell refinement: CrysAlis CCD (Oxford Diffraction, 2000); data reduction: CrysAlis RED (Oxford Diffraction, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Stereochemical Workstation (Siemens, 1989); software used to prepare material for publication: SHELXL97.

2,3,4,5,6-Pentafluorobenzamide

Crystal data

C7H2F5NO	F(000) = 416
Mr = 211.10	Dx = 1.884 Mg m^−3
Monoclinic, P21/c	Melting point = 146–149 K
Hall symbol: -P2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.7305 (11) Å	Cell parameters from 2021 reflections
b = 6.1929 (6) Å	θ = 4–25°
c = 9.5856 (10) Å	µ = 0.21 mm^−1
β = 100.073 (8)°	T = 120 K
V = 744.07 (12) Å^3	Prism, colorless
Z = 4	0.40 × 0.20 × 0.20 mm

Data collection

Kuma KM4CCD κ geometry diffractometer	1376 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
Graphite monochromator	θmax = 26.4°, θmin = 3.9°
ω scans	h = −15→15
4010 measured reflections	k = −7→7
1517 independent reflections	l = −11→5

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: difference Fourier map
wR(F^2) = 0.090	All H-atom parameters refined
S = 1.13	w = 1/[σ^2(Fo^2) + (0.048P)^2 + 0.2307P] where P = (Fo^2 + 2Fc^2)/3
1517 reflections	(Δ/σ)max = 0.002
135 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F2	0.28574 (7)	0.86929 (14)	−0.18731 (9)	0.0237 (2)
F3	0.44674 (7)	0.59609 (16)	−0.19947 (9)	0.0289 (3)
F4	0.45317 (8)	0.20334 (16)	−0.07058 (10)	0.0315 (3)
F5	0.29681 (8)	0.08965 (14)	0.07540 (9)	0.0275 (2)
F6	0.13508 (7)	0.35968 (14)	0.09104 (9)	0.0245 (2)
O1	0.09191 (9)	0.80167 (18)	0.09099 (11)	0.0234 (3)
N1	0.07115 (11)	0.8917 (2)	−0.14075 (13)	0.0222 (3)
C1	0.20388 (11)	0.6252 (2)	−0.04733 (14)	0.0171 (3)
C2	0.28496 (12)	0.6771 (2)	−0.12198 (15)	0.0185 (3)
C3	0.36913 (11)	0.5382 (3)	−0.12941 (15)	0.0212 (3)
C4	0.37288 (12)	0.3396 (2)	−0.06351 (16)	0.0220 (3)
C5	0.29319 (12)	0.2821 (2)	0.01045 (15)	0.0201 (3)
C6	0.21048 (12)	0.4238 (2)	0.01839 (14)	0.0186 (3)
C7	0.11637 (12)	0.7817 (2)	−0.02792 (15)	0.0184 (3)
H1	0.0887 (15)	0.862 (3)	−0.224 (2)	0.026 (5)*
H2	0.0205 (15)	0.986 (3)	−0.1306 (18)	0.024 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F2	0.0285 (5)	0.0240 (5)	0.0199 (4)	−0.0036 (4)	0.0081 (4)	0.0037 (4)
F3	0.0212 (5)	0.0415 (6)	0.0269 (5)	−0.0033 (4)	0.0119 (4)	−0.0030 (4)
F4	0.0261 (5)	0.0360 (6)	0.0326 (5)	0.0117 (4)	0.0058 (4)	−0.0058 (4)
F5	0.0390 (5)	0.0207 (5)	0.0222 (5)	0.0053 (4)	0.0038 (4)	0.0031 (4)
F6	0.0280 (5)	0.0247 (5)	0.0237 (5)	−0.0030 (4)	0.0122 (4)	0.0028 (4)
O1	0.0291 (6)	0.0279 (6)	0.0150 (5)	0.0074 (5)	0.0083 (4)	0.0020 (4)
N1	0.0267 (7)	0.0263 (7)	0.0152 (6)	0.0083 (6)	0.0080 (5)	0.0024 (5)
C1	0.0184 (7)	0.0200 (7)	0.0130 (6)	−0.0007 (6)	0.0028 (5)	−0.0021 (5)
C2	0.0222 (7)	0.0198 (7)	0.0138 (6)	−0.0028 (6)	0.0037 (5)	−0.0012 (5)
C3	0.0183 (7)	0.0305 (8)	0.0157 (7)	−0.0039 (6)	0.0053 (5)	−0.0049 (6)
C4	0.0196 (7)	0.0260 (8)	0.0198 (7)	0.0051 (6)	0.0021 (6)	−0.0069 (6)
C5	0.0264 (8)	0.0179 (7)	0.0149 (7)	0.0010 (6)	0.0005 (6)	−0.0009 (6)
C6	0.0211 (7)	0.0223 (7)	0.0130 (6)	−0.0021 (6)	0.0044 (5)	−0.0024 (5)
C7	0.0206 (7)	0.0198 (7)	0.0157 (7)	−0.0001 (6)	0.0054 (5)	−0.0006 (5)

Geometric parameters (Å, º)

F2—C2	1.3459 (17)	N1—H2	0.89 (2)
F3—C3	1.3370 (16)	C1—C2	1.393 (2)
F4—C4	1.3363 (17)	C1—C6	1.393 (2)
F5—C5	1.3419 (17)	C1—C7	1.513 (2)
F6—C6	1.3410 (16)	C2—C3	1.386 (2)
O1—C7	1.2392 (17)	C3—C4	1.380 (2)
N1—C7	1.3217 (19)	C4—C5	1.382 (2)
N1—H1	0.88 (2)	C5—C6	1.383 (2)
C7—N1—H1	119.2 (12)	F4—C4—C3	120.35 (14)
C7—N1—H2	118.0 (11)	F4—C4—C5	120.00 (14)
H1—N1—H2	122.6 (17)	C3—C4—C5	119.65 (13)
C2—C1—C6	116.59 (13)	F5—C5—C4	119.87 (13)
C2—C1—C7	122.90 (13)	F5—C5—C6	120.19 (13)
C6—C1—C7	120.37 (12)	C4—C5—C6	119.94 (14)
F2—C2—C3	117.15 (13)	F6—C6—C5	117.49 (13)
F2—C2—C1	120.65 (13)	F6—C6—C1	120.54 (13)
C3—C2—C1	122.18 (14)	C5—C6—C1	121.97 (13)
F3—C3—C4	119.97 (14)	O1—C7—N1	123.90 (14)
F3—C3—C2	120.36 (14)	O1—C7—C1	119.08 (13)
C4—C3—C2	119.66 (13)	N1—C7—C1	117.02 (12)
C2—C1—C7—O1	−134.44 (15)	C6—C1—C7—O1	41.2 (2)
C2—C1—C7—N1	44.8 (2)	C6—C1—C7—N1	−139.53 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.88 (2)	2.05 (2)	2.8902 (17)	158.3 (17)
N1—H2···O1^ii	0.89 (2)	2.03 (2)	2.9137 (17)	175.5 (16)

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x, −y+2, −z.