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In the title mol­ecular salt, C6H10N3O+·C2F3O2, the pyrimidinium cation is essentially planar, with a maximum deviation of 0.042 (3) Å for all non-H atoms. In the crystal, the cations and anions are linked via N—H...O hydrogen bonds, forming a centrosymmetric 2 + 2 aggregate with R22(8) and R42(8) ring motifs. These motifs are further linked through a pair of C—H...O hydrogen bonds into a supra­molecular tape along the [101] direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314616010105/su4055sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314616010105/su4055Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314616010105/su4055Isup3.cml
Supplementary material

CCDC reference: 1486919

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.065
  • wR factor = 0.245
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

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Alert level C PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.2 Note PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.6 Note PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.005 Ang. PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 3.176 Check PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 20 Report
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details found in the CIF Please Do ! PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large 0.14 Report PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note) 0.003 Degree PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 3 Note PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2014 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 6 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density 1 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 5 ALERT level C = Check. Ensure it is not caused by an omission or oversight 8 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 3 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: Due to the collabration between two Universities involving synthesis, collecting data and structure solution.

1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

2-Amino-4-methoxy-6-methylpyrimidin-1-ium trifluoroacetate top
Crystal data top
C6H10N3O+·C2F3O2Z = 2
Mr = 253.19F(000) = 260
Triclinic, P1Dx = 1.557 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.8087 (2) ÅCell parameters from 2385 reflections
b = 11.0283 (5) Åθ = 2.3–28.6°
c = 11.1135 (5) ŵ = 0.15 mm1
α = 108.704 (3)°T = 100 K
β = 96.174 (3)°Plate, colourless
γ = 100.533 (3)°0.37 × 0.21 × 0.07 mm
V = 540.03 (4) Å3
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
2467 independent reflections
Radiation source: fine-focus sealed tube1674 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
φ and ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 66
Tmin = 0.946, Tmax = 0.989k = 1414
8256 measured reflectionsl = 1414
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.245H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.1439P)2 + 0.1968P]
where P = (Fo2 + 2Fc2)/3
2467 reflections(Δ/σ)max < 0.001
168 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.43 e Å3
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat operating at 100.0 (1) K.

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.

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 > 2sigma(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
xyzUiso*/Ueq
O11.4551 (4)1.1091 (2)0.17382 (19)0.0228 (5)
N11.1022 (5)1.0528 (2)0.2807 (2)0.0167 (5)
N20.7855 (5)0.8428 (2)0.1855 (2)0.0163 (5)
N30.7455 (6)0.9851 (3)0.3832 (2)0.0195 (6)
C11.2280 (6)1.0222 (3)0.1804 (3)0.0158 (6)
C21.1430 (6)0.9018 (3)0.0739 (3)0.0179 (6)
H2A1.23850.88530.00170.021*
C30.9158 (6)0.8112 (3)0.0812 (3)0.0171 (6)
C40.8787 (6)0.9604 (3)0.2842 (2)0.0147 (6)
C51.5516 (7)1.2318 (3)0.2847 (3)0.0251 (7)
H5A1.72971.28340.27380.038*
H5B1.58651.21150.36390.038*
H5C1.40311.28250.29070.038*
C60.7968 (7)0.6779 (3)0.0186 (3)0.0230 (7)
H6A0.58680.66190.03800.035*
H6B0.85010.61100.01400.035*
H6C0.87530.67310.09740.035*
F10.1552 (5)0.49986 (19)0.3587 (2)0.0416 (6)
F20.1411 (5)0.6237 (2)0.4158 (2)0.0436 (6)
F30.1740 (4)0.50887 (18)0.21656 (18)0.0311 (5)
O20.3283 (4)0.66321 (19)0.20575 (18)0.0214 (5)
O30.2727 (5)0.8038 (2)0.39445 (19)0.0243 (5)
C70.0153 (7)0.5820 (3)0.3252 (3)0.0223 (7)
C80.2262 (6)0.6949 (3)0.3065 (3)0.0159 (6)
H1N30.807 (7)1.059 (4)0.446 (4)0.022 (8)*
H2N30.592 (9)0.925 (4)0.385 (4)0.035 (10)*
H1N20.628 (8)0.792 (4)0.197 (3)0.023 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0223 (11)0.0158 (11)0.0236 (11)0.0036 (8)0.0021 (9)0.0031 (9)
N10.0157 (12)0.0118 (11)0.0180 (11)0.0001 (9)0.0016 (9)0.0020 (9)
N20.0177 (13)0.0098 (11)0.0156 (11)0.0005 (9)0.0003 (9)0.0010 (9)
N30.0196 (13)0.0110 (12)0.0194 (12)0.0012 (10)0.0021 (10)0.0034 (10)
C10.0147 (14)0.0122 (13)0.0190 (13)0.0029 (11)0.0009 (10)0.0049 (11)
C20.0174 (14)0.0161 (14)0.0161 (13)0.0017 (11)0.0003 (11)0.0024 (11)
C30.0159 (14)0.0160 (14)0.0150 (12)0.0021 (11)0.0024 (10)0.0020 (11)
C40.0154 (13)0.0111 (13)0.0155 (12)0.0035 (10)0.0015 (10)0.0027 (10)
C50.0221 (16)0.0120 (14)0.0332 (16)0.0043 (11)0.0017 (13)0.0039 (12)
C60.0294 (17)0.0128 (14)0.0177 (13)0.0001 (12)0.0007 (12)0.0027 (11)
F10.0434 (13)0.0260 (11)0.0592 (14)0.0030 (9)0.0028 (10)0.0266 (10)
F20.0482 (14)0.0313 (11)0.0390 (12)0.0079 (10)0.0241 (10)0.0000 (9)
F30.0276 (11)0.0195 (9)0.0308 (10)0.0099 (8)0.0033 (8)0.0007 (8)
O20.0251 (12)0.0133 (10)0.0187 (10)0.0016 (8)0.0035 (8)0.0006 (8)
O30.0291 (12)0.0107 (10)0.0226 (11)0.0026 (8)0.0057 (9)0.0045 (8)
C70.0225 (15)0.0172 (15)0.0206 (14)0.0018 (12)0.0019 (12)0.0022 (12)
C80.0158 (14)0.0085 (12)0.0186 (13)0.0004 (10)0.0033 (10)0.0019 (10)
Geometric parameters (Å, º) top
O1—C11.340 (3)C3—C61.493 (4)
O1—C51.464 (4)C5—H5A0.9800
N1—C11.305 (3)C5—H5B0.9800
N1—C41.353 (3)C5—H5C0.9800
N2—C31.354 (3)C6—H6A0.9800
N2—C41.362 (3)C6—H6B0.9800
N2—H1N20.90 (4)C6—H6C0.9800
N3—C41.311 (3)F1—C71.341 (4)
N3—H1N30.86 (4)F2—C71.335 (3)
N3—H2N30.90 (4)F3—C71.344 (3)
C1—C21.422 (4)O2—C81.244 (3)
C2—C31.368 (4)O3—C81.244 (3)
C2—H2A0.9500C7—C81.540 (4)
C1—O1—C5116.5 (2)O1—C5—H5B109.5
C1—N1—C4116.7 (2)H5A—C5—H5B109.5
C3—N2—C4121.9 (2)O1—C5—H5C109.5
C3—N2—H1N2125 (2)H5A—C5—H5C109.5
C4—N2—H1N2113 (2)H5B—C5—H5C109.5
C4—N3—H1N3119 (2)C3—C6—H6A109.5
C4—N3—H2N3120 (2)C3—C6—H6B109.5
H1N3—N3—H2N3121 (3)H6A—C6—H6B109.5
N1—C1—O1119.1 (2)C3—C6—H6C109.5
N1—C1—C2125.2 (3)H6A—C6—H6C109.5
O1—C1—C2115.7 (2)H6B—C6—H6C109.5
C3—C2—C1116.1 (2)F2—C7—F1107.4 (2)
C3—C2—H2A121.9F2—C7—F3106.1 (2)
C1—C2—H2A121.9F1—C7—F3106.5 (2)
N2—C3—C2118.7 (2)F2—C7—C8113.2 (2)
N2—C3—C6116.6 (2)F1—C7—C8111.1 (2)
C2—C3—C6124.7 (2)F3—C7—C8112.1 (2)
N3—C4—N1119.5 (2)O2—C8—O3129.4 (2)
N3—C4—N2119.2 (3)O2—C8—C7114.8 (2)
N1—C4—N2121.3 (2)O3—C8—C7115.8 (2)
O1—C5—H5A109.5
C4—N1—C1—O1178.3 (2)C1—N1—C4—N3179.4 (3)
C4—N1—C1—C22.0 (4)C1—N1—C4—N21.9 (4)
C5—O1—C1—N12.3 (4)C3—N2—C4—N3179.4 (3)
C5—O1—C1—C2178.0 (2)C3—N2—C4—N11.8 (4)
N1—C1—C2—C31.9 (4)F2—C7—C8—O2164.9 (3)
O1—C1—C2—C3178.4 (2)F1—C7—C8—O274.2 (3)
C4—N2—C3—C21.7 (4)F3—C7—C8—O244.9 (4)
C4—N2—C3—C6178.6 (2)F2—C7—C8—O316.0 (4)
C1—C2—C3—N21.6 (4)F1—C7—C8—O3105.0 (3)
C1—C2—C3—C6178.7 (3)F3—C7—C8—O3135.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H1N3···O3i0.86 (4)2.05 (4)2.822 (3)148 (3)
N3—H2N3···O30.90 (4)1.88 (5)2.782 (4)178 (5)
N2—H1N2···O20.90 (4)1.86 (4)2.758 (3)170 (4)
C2—H2A···O1ii0.952.583.514 (4)168
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+3, y+2, z.
 

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