The title compound, C6H2F4N2O, displays amide bond lengths of 1.218 (3) Å and 1.366 (3) Å for the C=O and C—N bonds, respectively. The Cp—N—C—O (p = pyridine) torsion angle of 179.0 (2)° indicates an anti-conformation for the grouping. Intermolecular hydrogen bonding is observed between the amine N—H group and the carbonyl O atom, which generates chains of molecules propagating along the b-axis direction.
Supporting information
CCDC reference: 2196118
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.028
- wR factor = 0.066
- Data-to-parameter ratio = 10.7
checkCIF/PLATON results
No syntax errors found
Alert level C
STRVA01_ALERT_4_C Flack test results are meaningless.
From the CIF: _refine_ls_abs_structure_Flack -0.100
From the CIF: _refine_ls_abs_structure_Flack_su 0.600
| Author Response: While the s.u. value on the Flack parameter of -0.1(6)
shows a high uncertainty from the use of Mo radiation, the
absolute structure is likely correct, and is not used to establish
the absolute configuration of any chiral center.
|
PLAT048_ALERT_1_C MoietyFormula Not Given (or Incomplete) ........ Please Check
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........ 6.60 Note
| Author Response: When using the full set of 1309 reflections (as opposed to the
merged value of 806 reflections used by CheckCIF), the data to
parameter ratio is 10.73.
|
Alert level G
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High . 0.600 Report
PLAT432_ALERT_2_G Short Inter X...Y Contact N1 ..C5 . 3.03 Ang.
1/2+x,1/2-y,1-z = 4_556 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note
PLAT916_ALERT_2_G Hooft y and Flack x Parameter Values Differ by . 0.17 Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 3 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
5 ALERT level G = General information/check it is not something unexpected
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX3 (Bruker, 2018); cell refinement: SAINT (Bruker, 2018); data reduction: SAINT (Bruker, 2018); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
N-(2,3,5,6-Tetrafluoropyridin-4-yl)formamide
top
Crystal data top
C6H2F4N2O | Dx = 1.947 Mg m−3 |
Mr = 194.10 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 2461 reflections |
a = 5.1183 (4) Å | θ = 3.4–26.0° |
b = 6.2707 (6) Å | µ = 0.21 mm−1 |
c = 20.6294 (16) Å | T = 100 K |
V = 662.11 (10) Å3 | Column, colourless |
Z = 4 | 0.28 × 0.06 × 0.05 mm |
F(000) = 384 | |
Data collection top
Bruker D8 Venture Photon 2 diffractometer | 1200 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.029 |
φ and ω scans | θmax = 26.0°, θmin = 3.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2018) | h = −6→6 |
Tmin = 0.897, Tmax = 1.000 | k = −7→7 |
3556 measured reflections | l = −25→25 |
1309 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.066 | w = 1/[σ2(Fo2) + (0.0317P)2 + 0.041P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
1309 reflections | Δρmax = 0.14 e Å−3 |
122 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Absolute structure: Flack x determined using 424 quotients
[(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
Primary atom site location: dual | Absolute structure parameter: −0.1 (6) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
F1 | 0.9516 (3) | −0.1033 (2) | 0.60146 (7) | 0.0280 (4) | |
F2 | 0.5417 (3) | −0.0546 (2) | 0.68314 (6) | 0.0218 (4) | |
F3 | 0.3999 (3) | 0.6218 (2) | 0.58674 (7) | 0.0246 (4) | |
F4 | 0.8168 (3) | 0.5429 (2) | 0.51143 (7) | 0.0246 (4) | |
O1 | −0.0674 (4) | 0.4673 (3) | 0.73924 (8) | 0.0239 (4) | |
N1 | 0.8836 (4) | 0.2207 (3) | 0.55635 (10) | 0.0194 (5) | |
N2 | 0.2513 (4) | 0.3050 (3) | 0.68341 (10) | 0.0176 (5) | |
H2 | 0.208 (6) | 0.193 (5) | 0.7052 (15) | 0.030 (8)* | |
C1 | 0.8095 (5) | 0.0761 (4) | 0.59878 (12) | 0.0186 (6) | |
C2 | 0.6040 (5) | 0.0998 (4) | 0.64033 (11) | 0.0172 (5) | |
C3 | 0.4581 (5) | 0.2879 (4) | 0.64007 (11) | 0.0153 (5) | |
C4 | 0.5327 (5) | 0.4385 (4) | 0.59394 (11) | 0.0168 (5) | |
C5 | 0.7440 (5) | 0.3963 (4) | 0.55472 (11) | 0.0188 (6) | |
C6 | 0.1120 (5) | 0.4818 (4) | 0.70070 (12) | 0.0195 (6) | |
H6 | 0.155131 | 0.616615 | 0.682599 | 0.023* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.0275 (9) | 0.0267 (8) | 0.0299 (8) | 0.0124 (7) | 0.0063 (8) | 0.0033 (6) |
F2 | 0.0255 (8) | 0.0183 (7) | 0.0215 (7) | 0.0018 (7) | 0.0038 (7) | 0.0059 (6) |
F3 | 0.0292 (9) | 0.0193 (7) | 0.0253 (8) | 0.0059 (7) | 0.0041 (8) | 0.0053 (6) |
F4 | 0.0272 (8) | 0.0280 (8) | 0.0187 (7) | −0.0051 (7) | 0.0039 (7) | 0.0064 (6) |
O1 | 0.0232 (10) | 0.0228 (9) | 0.0255 (9) | 0.0014 (9) | 0.0100 (9) | −0.0038 (7) |
N1 | 0.0152 (11) | 0.0287 (11) | 0.0143 (10) | −0.0001 (9) | −0.0007 (10) | −0.0007 (8) |
N2 | 0.0183 (11) | 0.0174 (10) | 0.0170 (10) | −0.0002 (9) | 0.0036 (11) | 0.0011 (8) |
C1 | 0.0167 (13) | 0.0196 (12) | 0.0195 (12) | 0.0029 (10) | −0.0009 (12) | −0.0008 (10) |
C2 | 0.0183 (13) | 0.0185 (12) | 0.0149 (12) | −0.0013 (10) | −0.0003 (12) | 0.0013 (9) |
C3 | 0.0146 (11) | 0.0197 (11) | 0.0117 (11) | −0.0002 (10) | −0.0011 (11) | −0.0029 (8) |
C4 | 0.0182 (13) | 0.0176 (11) | 0.0146 (11) | 0.0010 (11) | −0.0021 (11) | 0.0005 (9) |
C5 | 0.0211 (13) | 0.0220 (12) | 0.0132 (12) | −0.0055 (11) | −0.0026 (12) | 0.0026 (10) |
C6 | 0.0198 (14) | 0.0183 (12) | 0.0205 (12) | 0.0005 (11) | 0.0016 (13) | −0.0021 (9) |
Geometric parameters (Å, º) top
F1—C1 | 1.341 (3) | N2—C3 | 1.390 (3) |
F2—C2 | 1.348 (3) | N2—H2 | 0.87 (3) |
F3—C4 | 1.343 (3) | C1—C2 | 1.365 (3) |
F4—C5 | 1.335 (3) | C2—C3 | 1.396 (3) |
O1—C6 | 1.218 (3) | C3—C4 | 1.394 (3) |
N1—C5 | 1.313 (3) | C4—C5 | 1.376 (4) |
N1—C1 | 1.316 (3) | C6—H6 | 0.9500 |
N2—C6 | 1.366 (3) | | |
| | | |
C5—N1—C1 | 116.0 (2) | N2—C3—C2 | 118.0 (2) |
C6—N2—C3 | 128.9 (2) | C4—C3—C2 | 115.4 (2) |
C6—N2—H2 | 113 (2) | F3—C4—C5 | 119.8 (2) |
C3—N2—H2 | 118 (2) | F3—C4—C3 | 121.1 (2) |
N1—C1—F1 | 116.7 (2) | C5—C4—C3 | 119.1 (2) |
N1—C1—C2 | 124.4 (2) | N1—C5—F4 | 116.3 (2) |
F1—C1—C2 | 118.9 (2) | N1—C5—C4 | 125.0 (2) |
F2—C2—C1 | 121.0 (2) | F4—C5—C4 | 118.7 (2) |
F2—C2—C3 | 118.9 (2) | O1—C6—N2 | 120.2 (2) |
C1—C2—C3 | 120.1 (2) | O1—C6—H6 | 119.9 |
N2—C3—C4 | 126.5 (2) | N2—C6—H6 | 119.9 |
| | | |
C5—N1—C1—F1 | −179.4 (2) | N2—C3—C4—F3 | −1.1 (4) |
C5—N1—C1—C2 | −0.8 (4) | C2—C3—C4—F3 | 176.8 (2) |
N1—C1—C2—F2 | −179.1 (2) | N2—C3—C4—C5 | 179.8 (2) |
F1—C1—C2—F2 | −0.6 (3) | C2—C3—C4—C5 | −2.3 (3) |
N1—C1—C2—C3 | −0.7 (4) | C1—N1—C5—F4 | −179.5 (2) |
F1—C1—C2—C3 | 177.9 (2) | C1—N1—C5—C4 | 0.7 (4) |
C6—N2—C3—C4 | −15.2 (4) | F3—C4—C5—N1 | −178.2 (2) |
C6—N2—C3—C2 | 167.0 (2) | C3—C4—C5—N1 | 0.9 (4) |
F2—C2—C3—N2 | −1.3 (3) | F3—C4—C5—F4 | 2.0 (3) |
C1—C2—C3—N2 | −179.8 (2) | C3—C4—C5—F4 | −178.9 (2) |
F2—C2—C3—C4 | −179.3 (2) | C3—N2—C6—O1 | 179.0 (2) |
C1—C2—C3—C4 | 2.2 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1i | 0.87 (3) | 1.96 (3) | 2.814 (3) | 171 (3) |
Symmetry code: (i) −x, y−1/2, −z+3/2. |