In the title compound, C
6H
7N
2O
+·C
2O
2F
3−, the carboxamide group is twisted by 16.3 (8)° from the pyridine ring plane. The protonated cations are linked to the anions by N—H
O hydrogen bonds to form a distorted lamellar structure.
Supporting information
CCDC reference: 647340
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- Disorder in main residue
- R factor = 0.066
- wR factor = 0.212
- Data-to-parameter ratio = 10.0
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for C12
| Author Response: As fluorine atoms are in disordered thermal parameters of these
atoms are high. Hence, the comparision with the C12 atom (neighbour) shows
low Ueq value.
|
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT213_ALERT_2_C Atom F1' has ADP max/min Ratio ............. 3.50 prola
PLAT213_ALERT_2_C Atom F2' has ADP max/min Ratio ............. 3.20 prola
PLAT220_ALERT_2_C Large Non-Solvent F Ueq(max)/Ueq(min) ... 2.62 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11
| Author Response: As fluorine atoms are in disordered thermal parameters of these
atoms are high. Hence, the comparision with the C12 atom (neighbour) shows
low Ueq value.
|
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.98
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.36
PLAT301_ALERT_3_C Main Residue Disorder ......................... 16.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.11 Ratio
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 8.80 Deg.
F2 -C12 -F2' 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 15.00 Deg.
F3' -C12 -F3 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 26.00 Deg.
F1' -C12 -F1 1.555 1.555 1.555
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
14 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
10 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL/PC (Bruker, 2000); program(s) used to refine structure: SHELXTL/PC; molecular graphics: ORTEP-3 (Farrugia, 1997), Mercury (Version 1.4.1; Macrae et al.,
2006) and
PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL/PC.
3-(Aminocarbonyl)pyridinium trifluoroacetate
top
Crystal data top
C6H7N2O+·C2O2F3− | F(000) = 480 |
Mr = 236.16 | Dx = 1.585 Mg m−3 Dm = 1.57 (2) Mg m−3 Dm measured by flotation technique using a liquid mixture of xylene and bromoform |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 10.045 (6) Å | θ = 9.2–13.5° |
b = 10.138 (8) Å | µ = 0.16 mm−1 |
c = 10.510 (7) Å | T = 293 K |
β = 112.42 (4)° | Block, colourless |
V = 989.4 (12) Å3 | 0.24 × 0.21 × 0.18 mm |
Z = 4 | |
Data collection top
Nonius MACH3 diffractometer | 778 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.034 |
Graphite monochromator | θmax = 25.0°, θmin = 2.2° |
ω/2θ scans | h = 0→11 |
Absorption correction: ψ scan (North et al., 1968) | k = −1→12 |
Tmin = 0.928, Tmax = 0.972 | l = −12→11 |
2054 measured reflections | 3 standard reflections every 60 min |
1727 independent reflections | intensity decay: none |
Refinement top
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.212 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.1123P)2] where P = (Fo2 + 2Fc2)/3 |
1727 reflections | (Δ/σ)max < 0.001 |
172 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
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. |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
N1 | 0.2470 (5) | 0.5824 (4) | 0.1126 (4) | 0.0680 (11) | |
H1 | 0.2354 | 0.5052 | 0.0762 | 0.082* | |
C2 | 0.1553 (6) | 0.6237 (4) | 0.1659 (5) | 0.0613 (12) | |
H2 | 0.0820 | 0.5679 | 0.1662 | 0.074* | |
C3 | 0.1663 (5) | 0.7489 (4) | 0.2216 (4) | 0.0577 (12) | |
C31 | 0.0666 (5) | 0.8027 (4) | 0.2843 (5) | 0.0616 (12) | |
N31 | −0.0161 (5) | 0.7156 (4) | 0.3159 (5) | 0.0811 (13) | |
H31A | −0.0744 | 0.7422 | 0.3529 | 0.097* | |
H31B | −0.0110 | 0.6331 | 0.2993 | 0.097* | |
O31 | 0.0649 (4) | 0.9216 (3) | 0.3052 (4) | 0.0829 (11) | |
C4 | 0.2790 (6) | 0.8253 (4) | 0.2201 (6) | 0.0748 (15) | |
H4 | 0.2914 | 0.9098 | 0.2572 | 0.090* | |
C5 | 0.3733 (7) | 0.7784 (5) | 0.1646 (6) | 0.0823 (16) | |
H5 | 0.4482 | 0.8313 | 0.1628 | 0.099* | |
C6 | 0.3567 (6) | 0.6554 (5) | 0.1129 (6) | 0.0740 (15) | |
H6 | 0.4216 | 0.6218 | 0.0776 | 0.089* | |
O11 | 0.3796 (5) | 0.3530 (4) | −0.0223 (5) | 0.1127 (17) | |
O12 | 0.1964 (4) | 0.3284 (3) | 0.0435 (4) | 0.0862 (12) | |
C11 | 0.2914 (6) | 0.2905 (5) | 0.0054 (5) | 0.0668 (13) | |
C12 | 0.3011 (9) | 0.1411 (5) | −0.0068 (7) | 0.0852 (19) | |
F1 | 0.428 (3) | 0.0949 (17) | 0.078 (3) | 0.142 (7) | 0.55 |
F1' | 0.390 (4) | 0.0918 (18) | 0.109 (4) | 0.175 (13) | 0.45 |
F2 | 0.3206 (18) | 0.1063 (16) | −0.1157 (18) | 0.170 (9) | 0.55 |
F2' | 0.300 (2) | 0.1002 (16) | −0.1274 (12) | 0.127 (8) | 0.45 |
F3 | 0.1831 (12) | 0.0780 (11) | −0.0108 (14) | 0.086 (3) | 0.55 |
F3' | 0.211 (3) | 0.067 (2) | 0.017 (4) | 0.227 (15) | 0.45 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.108 (3) | 0.037 (2) | 0.061 (3) | 0.006 (2) | 0.034 (2) | 0.0014 (18) |
C2 | 0.091 (3) | 0.033 (2) | 0.060 (3) | −0.003 (2) | 0.029 (3) | 0.004 (2) |
C3 | 0.087 (3) | 0.0226 (19) | 0.056 (3) | 0.002 (2) | 0.019 (2) | 0.0039 (18) |
C31 | 0.099 (3) | 0.023 (2) | 0.061 (3) | −0.002 (2) | 0.029 (3) | −0.0007 (19) |
N31 | 0.125 (3) | 0.041 (2) | 0.093 (3) | 0.012 (2) | 0.058 (3) | 0.002 (2) |
O31 | 0.123 (3) | 0.0363 (17) | 0.089 (2) | 0.0033 (19) | 0.040 (2) | −0.0085 (16) |
C4 | 0.111 (4) | 0.027 (2) | 0.084 (4) | −0.003 (3) | 0.034 (3) | −0.004 (2) |
C5 | 0.108 (4) | 0.041 (3) | 0.102 (4) | −0.007 (3) | 0.045 (4) | −0.004 (3) |
C6 | 0.092 (4) | 0.059 (3) | 0.075 (4) | 0.016 (3) | 0.037 (3) | 0.012 (3) |
O11 | 0.139 (4) | 0.060 (2) | 0.168 (5) | −0.008 (2) | 0.091 (4) | −0.003 (2) |
O12 | 0.134 (3) | 0.0457 (19) | 0.096 (3) | −0.006 (2) | 0.064 (3) | −0.0043 (18) |
C11 | 0.091 (3) | 0.041 (3) | 0.070 (3) | 0.003 (3) | 0.032 (3) | 0.001 (2) |
C12 | 0.132 (6) | 0.043 (3) | 0.075 (4) | 0.020 (4) | 0.033 (4) | −0.007 (3) |
F1 | 0.156 (11) | 0.078 (10) | 0.123 (11) | 0.057 (9) | −0.022 (8) | −0.037 (8) |
F1' | 0.22 (3) | 0.035 (7) | 0.16 (2) | −0.024 (11) | −0.051 (16) | 0.012 (9) |
F2 | 0.233 (15) | 0.117 (12) | 0.240 (19) | −0.050 (10) | 0.178 (15) | −0.091 (11) |
F2' | 0.178 (13) | 0.070 (8) | 0.066 (6) | 0.016 (8) | −0.028 (8) | −0.040 (6) |
F3 | 0.110 (6) | 0.040 (5) | 0.112 (6) | −0.015 (4) | 0.048 (5) | −0.017 (5) |
F3' | 0.32 (4) | 0.052 (9) | 0.28 (3) | −0.011 (14) | 0.09 (3) | 0.050 (12) |
Geometric parameters (Å, º) top
N1—C2 | 1.316 (6) | C5—H5 | 0.9300 |
N1—C6 | 1.326 (6) | C6—H6 | 0.9300 |
N1—H1 | 0.8600 | O11—C11 | 1.211 (6) |
C2—C3 | 1.385 (6) | O12—C11 | 1.228 (6) |
C2—H2 | 0.9300 | C11—C12 | 1.527 (7) |
C3—C4 | 1.377 (6) | C12—F3' | 1.28 (3) |
C3—C31 | 1.496 (6) | C12—F2 | 1.282 (13) |
C31—O31 | 1.227 (5) | C12—F1' | 1.31 (3) |
C31—N31 | 1.338 (5) | C12—F2' | 1.329 (14) |
N31—H31A | 0.8600 | C12—F3 | 1.334 (13) |
N31—H31B | 0.8600 | C12—F1 | 1.33 (2) |
C4—C5 | 1.373 (7) | F1—F1' | 0.59 (5) |
C4—H4 | 0.9300 | F1'—F3' | 1.71 (4) |
C5—C6 | 1.344 (7) | | |
| | | |
C2—N1—C6 | 122.5 (4) | F3'—C12—F2 | 112.0 (17) |
C2—N1—H1 | 118.8 | F3'—C12—F1' | 82.8 (19) |
C6—N1—H1 | 118.8 | F2—C12—F1' | 116.6 (17) |
N1—C2—C3 | 121.1 (4) | F3'—C12—F2' | 104.7 (16) |
N1—C2—H2 | 119.5 | F2—C12—F2' | 8.8 (14) |
C3—C2—H2 | 119.5 | F1'—C12—F2' | 121.8 (16) |
C4—C3—C2 | 116.3 (4) | F3'—C12—F3 | 15 (2) |
C4—C3—C31 | 119.5 (4) | F2—C12—F3 | 106.1 (9) |
C2—C3—C31 | 124.2 (4) | F1'—C12—F3 | 97.4 (17) |
O31—C31—N31 | 123.5 (4) | F2'—C12—F3 | 97.8 (12) |
O31—C31—C3 | 119.6 (4) | F3'—C12—F1 | 103.4 (19) |
N31—C31—C3 | 116.9 (3) | F2—C12—F1 | 94.0 (14) |
C31—N31—H31A | 120.0 | F1'—C12—F1 | 26 (2) |
C31—N31—H31B | 120.0 | F2'—C12—F1 | 100.9 (13) |
H31A—N31—H31B | 120.0 | F3—C12—F1 | 117.7 (13) |
C5—C4—C3 | 120.9 (4) | F3'—C12—C11 | 119.8 (13) |
C5—C4—H4 | 119.5 | F2—C12—C11 | 112.6 (9) |
C3—C4—H4 | 119.5 | F1'—C12—C11 | 110.1 (11) |
C6—C5—C4 | 119.6 (5) | F2'—C12—C11 | 114.3 (9) |
C6—C5—H5 | 120.2 | F3—C12—C11 | 113.2 (7) |
C4—C5—H5 | 120.2 | F1—C12—C11 | 111.5 (10) |
N1—C6—C5 | 119.6 (5) | F1'—F1—C12 | 74 (5) |
N1—C6—H6 | 120.2 | F1—F1'—C12 | 80 (5) |
C5—C6—H6 | 120.2 | F1—F1'—F3' | 117 (7) |
O11—C11—O12 | 130.2 (5) | C12—F1'—F3' | 47.9 (14) |
O11—C11—C12 | 115.0 (5) | C12—F3'—F1' | 49.3 (14) |
O12—C11—C12 | 114.8 (5) | | |
| | | |
C6—N1—C2—C3 | 2.2 (7) | O12—C11—C12—F1 | −118.3 (13) |
N1—C2—C3—C4 | −1.2 (7) | F3'—C12—F1—F1' | −38 (4) |
N1—C2—C3—C31 | −179.8 (4) | F2—C12—F1—F1' | −152 (4) |
C4—C3—C31—O31 | 16.4 (7) | F2'—C12—F1—F1' | −146 (4) |
C2—C3—C31—O31 | −165.0 (5) | F3—C12—F1—F1' | −41 (4) |
C4—C3—C31—N31 | −163.0 (4) | C11—C12—F1—F1' | 92 (4) |
C2—C3—C31—N31 | 15.6 (7) | C12—F1—F1'—F3' | 30 (2) |
C2—C3—C4—C5 | 0.6 (7) | F3'—C12—F1'—F1 | 143 (4) |
C31—C3—C4—C5 | 179.3 (5) | F2—C12—F1'—F1 | 32 (4) |
C3—C4—C5—C6 | −1.0 (9) | F2'—C12—F1'—F1 | 40 (4) |
C2—N1—C6—C5 | −2.6 (8) | F3—C12—F1'—F1 | 144 (4) |
C4—C5—C6—N1 | 1.9 (8) | C11—C12—F1'—F1 | −98 (4) |
O11—C11—C12—F3' | −178 (2) | F2—C12—F1'—F3' | −111.0 (18) |
O12—C11—C12—F3' | 3 (2) | F2'—C12—F1'—F3' | −102.8 (19) |
O11—C11—C12—F2 | −43.4 (11) | F3—C12—F1'—F3' | 1.1 (16) |
O12—C11—C12—F2 | 137.4 (10) | F1—C12—F1'—F3' | −143 (4) |
O11—C11—C12—F1' | 88.5 (18) | C11—C12—F1'—F3' | 119.2 (15) |
O12—C11—C12—F1' | −90.6 (19) | F2—C12—F3'—F1' | 115.8 (17) |
O11—C11—C12—F2' | −52.8 (12) | F2'—C12—F3'—F1' | 121.0 (16) |
O12—C11—C12—F2' | 128.0 (11) | F3—C12—F3'—F1' | −176 (7) |
O11—C11—C12—F3 | −163.7 (8) | F1—C12—F3'—F1' | 16 (2) |
O12—C11—C12—F3 | 17.2 (10) | C11—C12—F3'—F1' | −109.1 (15) |
O11—C11—C12—F1 | 60.9 (13) | F1—F1'—F3'—C12 | −42 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O12 | 0.86 | 1.84 | 2.671 (5) | 163 |
N31—H31A···O12i | 0.86 | 2.11 | 2.969 (5) | 172 |
N31—H31B···O31ii | 0.86 | 2.38 | 3.205 (5) | 162 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x, y−1/2, −z+1/2. |