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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 R_2^2(8) and chain C(4) motifs.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021871/cm6057sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021871/cm6057Isup2.hkl
Contains datablock I

CCDC reference: 226950

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

No syntax errors found


No errors found in this datablock

Computing details top

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 top
Crystal data top
C7H2F5NOF(000) = 416
Mr = 211.10Dx = 1.884 Mg m3
Monoclinic, P21/cMelting point = 146–149 K
Hall symbol: -P2ybcMo Kα radiation, λ = 0.71073 Å
a = 12.7305 (11) ÅCell parameters from 2021 reflections
b = 6.1929 (6) Åθ = 4–25°
c = 9.5856 (10) ŵ = 0.21 mm1
β = 100.073 (8)°T = 120 K
V = 744.07 (12) Å3Prism, colorless
Z = 40.40 × 0.20 × 0.20 mm
Data collection top
Kuma KM4CCD κ geometry
diffractometer
1376 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.016
Graphite monochromatorθmax = 26.4°, θmin = 3.9°
ω scansh = 1515
4010 measured reflectionsk = 77
1517 independent reflectionsl = 115
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: difference Fourier map
wR(F2) = 0.090All H-atom parameters refined
S = 1.13 w = 1/[σ2(Fo2) + (0.048P)2 + 0.2307P]
where P = (Fo2 + 2Fc2)/3
1517 reflections(Δ/σ)max = 0.002
135 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.26 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F20.28574 (7)0.86929 (14)0.18731 (9)0.0237 (2)
F30.44674 (7)0.59609 (16)0.19947 (9)0.0289 (3)
F40.45317 (8)0.20334 (16)0.07058 (10)0.0315 (3)
F50.29681 (8)0.08965 (14)0.07540 (9)0.0275 (2)
F60.13508 (7)0.35968 (14)0.09104 (9)0.0245 (2)
O10.09191 (9)0.80167 (18)0.09099 (11)0.0234 (3)
N10.07115 (11)0.8917 (2)0.14075 (13)0.0222 (3)
C10.20388 (11)0.6252 (2)0.04733 (14)0.0171 (3)
C20.28496 (12)0.6771 (2)0.12198 (15)0.0185 (3)
C30.36913 (11)0.5382 (3)0.12941 (15)0.0212 (3)
C40.37288 (12)0.3396 (2)0.06351 (16)0.0220 (3)
C50.29319 (12)0.2821 (2)0.01045 (15)0.0201 (3)
C60.21048 (12)0.4238 (2)0.01839 (14)0.0186 (3)
C70.11637 (12)0.7817 (2)0.02792 (15)0.0184 (3)
H10.0887 (15)0.862 (3)0.224 (2)0.026 (5)*
H20.0205 (15)0.986 (3)0.1306 (18)0.024 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F20.0285 (5)0.0240 (5)0.0199 (4)0.0036 (4)0.0081 (4)0.0037 (4)
F30.0212 (5)0.0415 (6)0.0269 (5)0.0033 (4)0.0119 (4)0.0030 (4)
F40.0261 (5)0.0360 (6)0.0326 (5)0.0117 (4)0.0058 (4)0.0058 (4)
F50.0390 (5)0.0207 (5)0.0222 (5)0.0053 (4)0.0038 (4)0.0031 (4)
F60.0280 (5)0.0247 (5)0.0237 (5)0.0030 (4)0.0122 (4)0.0028 (4)
O10.0291 (6)0.0279 (6)0.0150 (5)0.0074 (5)0.0083 (4)0.0020 (4)
N10.0267 (7)0.0263 (7)0.0152 (6)0.0083 (6)0.0080 (5)0.0024 (5)
C10.0184 (7)0.0200 (7)0.0130 (6)0.0007 (6)0.0028 (5)0.0021 (5)
C20.0222 (7)0.0198 (7)0.0138 (6)0.0028 (6)0.0037 (5)0.0012 (5)
C30.0183 (7)0.0305 (8)0.0157 (7)0.0039 (6)0.0053 (5)0.0049 (6)
C40.0196 (7)0.0260 (8)0.0198 (7)0.0051 (6)0.0021 (6)0.0069 (6)
C50.0264 (8)0.0179 (7)0.0149 (7)0.0010 (6)0.0005 (6)0.0009 (6)
C60.0211 (7)0.0223 (7)0.0130 (6)0.0021 (6)0.0044 (5)0.0024 (5)
C70.0206 (7)0.0198 (7)0.0157 (7)0.0001 (6)0.0054 (5)0.0006 (5)
Geometric parameters (Å, º) top
F2—C21.3459 (17)N1—H20.89 (2)
F3—C31.3370 (16)C1—C21.393 (2)
F4—C41.3363 (17)C1—C61.393 (2)
F5—C51.3419 (17)C1—C71.513 (2)
F6—C61.3410 (16)C2—C31.386 (2)
O1—C71.2392 (17)C3—C41.380 (2)
N1—C71.3217 (19)C4—C51.382 (2)
N1—H10.88 (2)C5—C61.383 (2)
C7—N1—H1119.2 (12)F4—C4—C3120.35 (14)
C7—N1—H2118.0 (11)F4—C4—C5120.00 (14)
H1—N1—H2122.6 (17)C3—C4—C5119.65 (13)
C2—C1—C6116.59 (13)F5—C5—C4119.87 (13)
C2—C1—C7122.90 (13)F5—C5—C6120.19 (13)
C6—C1—C7120.37 (12)C4—C5—C6119.94 (14)
F2—C2—C3117.15 (13)F6—C6—C5117.49 (13)
F2—C2—C1120.65 (13)F6—C6—C1120.54 (13)
C3—C2—C1122.18 (14)C5—C6—C1121.97 (13)
F3—C3—C4119.97 (14)O1—C7—N1123.90 (14)
F3—C3—C2120.36 (14)O1—C7—C1119.08 (13)
C4—C3—C2119.66 (13)N1—C7—C1117.02 (12)
C2—C1—C7—O1134.44 (15)C6—C1—C7—O141.2 (2)
C2—C1—C7—N144.8 (2)C6—C1—C7—N1139.53 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.88 (2)2.05 (2)2.8902 (17)158.3 (17)
N1—H2···O1ii0.89 (2)2.03 (2)2.9137 (17)175.5 (16)
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x, y+2, z.
 

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