Literature DB >> 21580433

2-Amino-pyridinium trifluoro-acetate.

Madhukar Hemamalini1, Hoong-Kun Fun.   

Abstract

The asymmetric unit of the title compound, C(5)H(7)N(2) (+)·C(2)F(3)O(2) (-), contains four independent 2-amino-pyridinium cations and four independent trifluoro-acetate anions. In the crystal structure, these ions are linked by N-H⋯O hydrogen bonds, forming four cation-anion pairs each containing an R(2) (2)(8) ring motif. The ion pairs are linked into two independent chains along [100] by N-H⋯O hydrogen bonds. In addition, C-H⋯O and C-H⋯F hydrogen bonds and π⋯π inter-actions [centoid-centroid separation = 3.6007 (17) Å] are observed.

Entities:  

Year:  2010        PMID： 21580433      PMCID： PMC2983566          DOI： 10.1107/S1600536810006392

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For background to the chemistry of substituted pyridines, see: Pozharski et al. (1997 ▶); Katritzky et al. (1996 ▶). For related structures, see: Chao et al. (1975 ▶); Gellert & Hsu (1988 ▶); Demir et al. (2005 ▶); Jebas et al. (2006 ▶); Rademeyer (2007 ▶); Windholz (1976 ▶). For details of hydrogen bonding, see: Jeffrey & Saenger (1991 ▶); Jeffrey (1997 ▶); Scheiner (1997 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C5H7N2 +·C2F3O2 − M = 208.15 Monoclinic, a = 11.4641 (15) Å b = 10.0221 (13) Å c = 29.928 (4) Å β = 92.918 (3)° V = 3434.1 (8) Å3 Z = 16 Mo Kα radiation μ = 0.16 mm−1 T = 100 K 0.35 × 0.17 × 0.04 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.947, T max = 0.994 28669 measured reflections 6732 independent reflections 4154 reflections with I > 2σ(I) R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.044 wR(F 2) = 0.141 S = 1.02 6732 reflections 617 parameters All H-atom parameters refined Δρmax = 0.44 e Å−3 Δρmin = −0.44 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810006392/ci5036sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006392/ci5036Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C5H7N2+·C2F3O2−F(000) = 1696
Mr = 208.15Dx = 1.610 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3066 reflections
a = 11.4641 (15) Åθ = 2.7–24.0°
b = 10.0221 (13) ŵ = 0.16 mm−1
c = 29.928 (4) ÅT = 100 K
β = 92.918 (3)°Plate, colourless
V = 3434.1 (8) Å30.35 × 0.17 × 0.04 mm
Z = 16
Bruker APEX DUO CCD area-detector diffractometer6732 independent reflections
Radiation source: fine-focus sealed tube4154 reflections with I > 2σ(I)
graphiteRint = 0.072
φ and ω scansθmax = 26.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −14→12
Tmin = 0.947, Tmax = 0.994k = −12→12
28669 measured reflectionsl = −36→36
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141All H-atom parameters refined
S = 1.02w = 1/[σ2(Fo2) + (0.072P)2] where P = (Fo2 + 2Fc2)/3
6732 reflections(Δ/σ)max = 0.001
617 parametersΔρmax = 0.44 e Å−3
0 restraintsΔρmin = −0.44 e Å−3
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.
xyzUiso*/Ueq
N1A0.53238 (18)0.6375 (2)0.03514 (8)0.0211 (5)
N2A0.7286 (2)0.6627 (3)0.02401 (9)0.0266 (6)
C1A0.4393 (2)0.5710 (3)0.05182 (10)0.0248 (7)
C2A0.4546 (3)0.4564 (3)0.07439 (10)0.0271 (7)
C3A0.5680 (2)0.4031 (3)0.08038 (10)0.0246 (7)
C4A0.6604 (2)0.4684 (3)0.06365 (10)0.0248 (7)
C5A0.6430 (2)0.5902 (3)0.04029 (9)0.0218 (6)
F1A−0.04773 (14)0.44273 (16)0.07172 (5)0.0314 (4)
F2A0.06503 (16)0.56750 (19)0.11269 (6)0.0419 (5)
F3A0.13664 (14)0.40701 (17)0.07542 (6)0.0347 (4)
O1A−0.01983 (15)0.65268 (18)0.01836 (6)0.0218 (4)
O2A0.17434 (15)0.6235 (2)0.02589 (7)0.0289 (5)
C6A0.0564 (2)0.5042 (3)0.07342 (9)0.0231 (6)
C7A0.0723 (2)0.6020 (3)0.03494 (9)0.0187 (6)
N1B0.25015 (19)0.0690 (2)0.22063 (8)0.0223 (5)
N2B0.4426 (2)0.0544 (3)0.24561 (10)0.0327 (7)
C1B0.1593 (3)0.1252 (3)0.19635 (10)0.0290 (7)
C2B0.1754 (3)0.2363 (3)0.17180 (11)0.0352 (8)
C3B0.2877 (3)0.2902 (3)0.17187 (11)0.0365 (8)
C4B0.3786 (3)0.2344 (3)0.19497 (11)0.0342 (8)
C5B0.3600 (2)0.1179 (3)0.22101 (10)0.0265 (7)
F1B0.19140 (15)0.79602 (17)0.16527 (6)0.0357 (4)
F2B0.31202 (16)0.64578 (17)0.14540 (6)0.0391 (5)
F3B0.36394 (14)0.78893 (16)0.19615 (6)0.0326 (4)
O1B0.12827 (16)0.5810 (2)0.21178 (7)0.0306 (5)
O2B0.30890 (15)0.57592 (19)0.24392 (6)0.0237 (5)
C6B0.2742 (2)0.7125 (3)0.18099 (10)0.0240 (7)
C7B0.2322 (2)0.6146 (3)0.21597 (9)0.0220 (6)
N1C0.97689 (18)0.1324 (2)0.03769 (8)0.0195 (5)
N2C0.7775 (2)0.1534 (3)0.02793 (9)0.0234 (6)
C1C1.0764 (2)0.0718 (3)0.05421 (10)0.0233 (7)
C2C1.0705 (3)−0.0409 (3)0.07859 (10)0.0259 (7)
C3C0.9596 (3)−0.0928 (3)0.08655 (10)0.0259 (7)
C4C0.8602 (2)−0.0311 (3)0.07060 (10)0.0229 (6)
C5C0.8686 (2)0.0864 (3)0.04501 (9)0.0187 (6)
F1C0.70647 (15)0.14098 (17)0.14889 (6)0.0361 (5)
F2C0.83699 (16)0.28461 (17)0.13276 (6)0.0383 (5)
F3C0.87288 (13)0.14044 (16)0.18453 (5)0.0290 (4)
O1C0.64277 (16)0.3622 (2)0.19178 (7)0.0296 (5)
O2C0.81484 (15)0.35674 (19)0.23072 (6)0.0243 (5)
C6C0.7897 (2)0.2205 (3)0.16693 (9)0.0235 (7)
C7C0.7438 (2)0.3217 (3)0.20015 (9)0.0215 (6)
N1D0.75292 (18)0.8656 (2)0.20606 (8)0.0203 (5)
N2D0.9457 (2)0.8664 (3)0.23238 (9)0.0272 (6)
C1D0.6606 (2)0.8152 (3)0.18099 (10)0.0252 (7)
C2D0.6725 (3)0.7041 (3)0.15644 (10)0.0293 (7)
C3D0.7819 (3)0.6428 (3)0.15695 (10)0.0283 (7)
C4D0.8744 (3)0.6922 (3)0.18151 (10)0.0253 (7)
C5D0.8595 (2)0.8081 (3)0.20725 (9)0.0216 (6)
F1D0.38550 (14)0.89359 (17)0.07557 (6)0.0363 (5)
F2D0.45932 (18)1.0533 (2)0.11547 (6)0.0484 (5)
F3D0.56876 (14)0.93681 (17)0.07456 (6)0.0355 (5)
O1D0.33350 (16)1.1182 (2)0.02989 (8)0.0394 (6)
O2D0.52497 (15)1.14436 (19)0.02069 (6)0.0238 (5)
C6D0.4630 (2)0.9937 (3)0.07548 (10)0.0261 (7)
C7D0.4378 (2)1.0945 (3)0.03804 (10)0.0245 (7)
H1A0.364 (3)0.615 (3)0.0418 (9)0.026 (8)*
H2A0.383 (3)0.406 (3)0.0863 (11)0.050 (10)*
H3A0.579 (3)0.315 (3)0.0972 (10)0.037 (9)*
H4A0.748 (3)0.435 (3)0.0678 (9)0.031 (8)*
H1NA0.525 (2)0.710 (3)0.0166 (9)0.016 (7)*
H2NA0.697 (4)0.743 (4)0.0063 (13)0.080 (14)*
H3NA0.799 (3)0.641 (3)0.0250 (11)0.052 (11)*
H1B0.076 (3)0.081 (3)0.2000 (10)0.042 (9)*
H2B0.100 (3)0.280 (3)0.1548 (11)0.057 (11)*
H3B0.297 (3)0.364 (3)0.1548 (11)0.041 (10)*
H4B0.466 (3)0.266 (3)0.1957 (10)0.044 (9)*
H1NB0.240 (3)−0.011 (3)0.2385 (9)0.031 (9)*
H2NB0.430 (3)−0.007 (4)0.2673 (11)0.043 (11)*
H3NB0.511 (3)0.087 (3)0.2509 (10)0.038 (10)*
H1C1.148 (2)0.110 (3)0.0459 (9)0.022 (8)*
H2C1.139 (3)−0.086 (3)0.0906 (10)0.035 (9)*
H3C0.955 (2)−0.174 (3)0.1037 (10)0.029 (8)*
H4C0.787 (3)−0.064 (3)0.0765 (9)0.027 (8)*
H1NC0.984 (3)0.202 (3)0.0213 (10)0.029 (9)*
H2NC0.792 (3)0.222 (3)0.0099 (11)0.049 (11)*
H3NC0.701 (3)0.121 (4)0.0304 (12)0.062 (12)*
H1D0.583 (2)0.864 (3)0.1846 (9)0.023 (7)*
H2D0.603 (3)0.670 (3)0.1391 (10)0.034 (8)*
H3D0.791 (2)0.560 (3)0.1406 (9)0.027 (8)*
H4D0.961 (2)0.650 (3)0.1830 (9)0.027 (8)*
H1ND0.746 (2)0.938 (3)0.2247 (9)0.026 (8)*
H2ND0.940 (2)0.937 (3)0.2533 (10)0.026 (8)*
H3ND1.009 (3)0.826 (3)0.2377 (10)0.032 (9)*
U11U22U33U12U13U23
N1A0.0145 (12)0.0229 (14)0.0259 (14)0.0006 (10)0.0017 (10)−0.0020 (12)
N2A0.0104 (12)0.0265 (15)0.0431 (17)0.0006 (10)0.0041 (11)−0.0005 (12)
C1A0.0138 (14)0.0332 (18)0.0275 (17)−0.0003 (12)0.0023 (12)−0.0038 (14)
C2A0.0248 (16)0.0342 (18)0.0227 (17)−0.0062 (13)0.0035 (12)−0.0053 (14)
C3A0.0236 (15)0.0272 (17)0.0230 (17)−0.0034 (13)0.0014 (12)−0.0061 (14)
C4A0.0209 (15)0.0246 (16)0.0285 (17)0.0018 (12)−0.0021 (12)−0.0022 (14)
C5A0.0171 (14)0.0240 (16)0.0246 (16)−0.0012 (11)0.0020 (11)−0.0063 (13)
F1A0.0229 (9)0.0390 (11)0.0329 (10)−0.0065 (7)0.0054 (7)0.0108 (8)
F2A0.0512 (12)0.0532 (13)0.0209 (10)−0.0013 (9)−0.0012 (8)−0.0068 (9)
F3A0.0275 (9)0.0362 (10)0.0404 (11)0.0104 (8)0.0016 (8)0.0155 (9)
O1A0.0134 (9)0.0236 (11)0.0283 (11)0.0014 (8)0.0007 (8)0.0043 (9)
O2A0.0123 (10)0.0337 (12)0.0409 (13)−0.0013 (8)0.0015 (8)0.0128 (10)
C6A0.0167 (14)0.0278 (17)0.0247 (17)−0.0001 (12)−0.0005 (11)0.0022 (14)
C7A0.0153 (14)0.0185 (15)0.0222 (15)−0.0001 (11)−0.0010 (11)−0.0006 (12)
N1B0.0181 (12)0.0207 (13)0.0285 (14)−0.0021 (10)0.0046 (10)0.0000 (11)
N2B0.0184 (14)0.0388 (17)0.0407 (18)−0.0071 (12)0.0006 (12)−0.0067 (15)
C1B0.0272 (16)0.0269 (17)0.0329 (19)0.0056 (13)0.0017 (13)−0.0004 (14)
C2B0.046 (2)0.0289 (19)0.0311 (19)0.0078 (15)0.0098 (15)0.0050 (15)
C3B0.056 (2)0.0247 (19)0.031 (2)0.0006 (16)0.0200 (16)0.0015 (16)
C4B0.043 (2)0.0269 (18)0.0346 (19)−0.0140 (15)0.0184 (15)−0.0088 (15)
C5B0.0237 (16)0.0253 (17)0.0312 (18)−0.0036 (13)0.0088 (13)−0.0102 (14)
F1B0.0408 (11)0.0322 (10)0.0334 (11)0.0069 (8)−0.0045 (8)0.0080 (8)
F2B0.0535 (12)0.0365 (11)0.0288 (11)0.0006 (9)0.0179 (8)−0.0056 (9)
F3B0.0310 (10)0.0300 (10)0.0369 (11)−0.0055 (8)0.0029 (8)0.0029 (8)
O1B0.0203 (11)0.0425 (13)0.0286 (12)−0.0044 (9)−0.0027 (8)0.0026 (10)
O2B0.0171 (10)0.0271 (11)0.0267 (11)0.0021 (8)−0.0008 (8)0.0026 (9)
C6B0.0215 (15)0.0244 (16)0.0258 (17)0.0021 (12)−0.0011 (12)−0.0041 (13)
C7B0.0207 (15)0.0248 (16)0.0205 (16)0.0028 (12)0.0023 (12)−0.0052 (13)
N1C0.0163 (12)0.0183 (13)0.0239 (14)0.0000 (9)0.0024 (10)0.0029 (11)
N2C0.0123 (12)0.0249 (15)0.0330 (16)−0.0029 (10)0.0013 (10)0.0035 (12)
C1C0.0156 (15)0.0299 (17)0.0245 (16)0.0007 (12)0.0013 (11)0.0016 (13)
C2C0.0219 (15)0.0303 (18)0.0253 (17)0.0084 (13)0.0003 (12)0.0050 (14)
C3C0.0346 (17)0.0183 (16)0.0254 (17)0.0011 (13)0.0074 (13)0.0061 (13)
C4C0.0198 (15)0.0208 (16)0.0287 (17)−0.0012 (12)0.0071 (12)0.0006 (13)
C5C0.0159 (14)0.0187 (15)0.0216 (15)−0.0028 (11)0.0025 (11)−0.0027 (12)
F1C0.0356 (10)0.0326 (10)0.0391 (11)−0.0034 (8)−0.0100 (8)−0.0083 (9)
F2C0.0545 (12)0.0334 (11)0.0283 (11)−0.0007 (9)0.0146 (8)0.0082 (8)
F3C0.0258 (9)0.0295 (10)0.0316 (10)0.0060 (7)0.0007 (7)0.0014 (8)
O1C0.0192 (11)0.0336 (12)0.0354 (13)0.0032 (9)−0.0037 (9)0.0000 (10)
O2C0.0172 (10)0.0266 (11)0.0288 (12)−0.0003 (8)−0.0025 (8)−0.0050 (9)
C6C0.0214 (15)0.0242 (16)0.0247 (16)−0.0021 (12)−0.0011 (12)0.0063 (13)
C7C0.0197 (15)0.0220 (16)0.0228 (16)−0.0031 (11)0.0017 (12)0.0039 (12)
N1D0.0162 (12)0.0202 (13)0.0244 (14)0.0004 (10)0.0007 (10)−0.0004 (11)
N2D0.0155 (13)0.0337 (16)0.0322 (16)0.0024 (11)−0.0021 (11)0.0024 (13)
C1D0.0200 (15)0.0279 (17)0.0277 (17)−0.0038 (12)0.0007 (12)0.0021 (14)
C2D0.0313 (17)0.0258 (17)0.0310 (18)−0.0058 (13)0.0026 (14)−0.0024 (14)
C3D0.0374 (18)0.0200 (17)0.0283 (18)−0.0011 (14)0.0080 (14)−0.0003 (14)
C4D0.0295 (17)0.0217 (16)0.0256 (17)0.0053 (13)0.0093 (13)0.0057 (13)
C5D0.0199 (15)0.0238 (16)0.0214 (16)0.0005 (11)0.0052 (11)0.0088 (12)
F1D0.0292 (10)0.0351 (10)0.0449 (12)−0.0034 (8)0.0047 (8)0.0097 (9)
F2D0.0641 (14)0.0538 (13)0.0277 (11)0.0036 (10)0.0064 (9)−0.0105 (10)
F3D0.0227 (9)0.0446 (11)0.0386 (11)0.0077 (8)−0.0039 (7)0.0054 (9)
O1D0.0132 (11)0.0437 (14)0.0617 (16)0.0031 (9)0.0068 (10)0.0201 (12)
O2D0.0146 (10)0.0283 (11)0.0287 (12)−0.0023 (8)0.0046 (8)−0.0017 (9)
C6D0.0208 (15)0.0291 (17)0.0287 (18)−0.0018 (12)0.0025 (12)−0.0077 (14)
C7D0.0149 (14)0.0272 (17)0.0315 (17)0.0002 (12)0.0036 (12)−0.0035 (14)
N1A—C5A1.355 (3)N1C—C5C1.353 (3)
N1A—C1A1.373 (4)N1C—C1C1.363 (3)
N1A—H1NA0.92 (3)N1C—H1NC0.86 (3)
N2A—C5A1.334 (4)N2C—C5C1.323 (3)
N2A—H2NA1.02 (4)N2C—H2NC0.90 (3)
N2A—H3NA0.83 (4)N2C—H3NC0.94 (4)
C1A—C2A1.340 (4)C1C—C2C1.348 (4)
C1A—H1A1.00 (3)C1C—H1C0.95 (3)
C2A—C3A1.409 (4)C2C—C3C1.406 (4)
C2A—H2A1.04 (3)C2C—H2C0.96 (3)
C3A—C4A1.362 (4)C3C—C4C1.361 (4)
C3A—H3A1.02 (3)C3C—H3C0.97 (3)
C4A—C5A1.416 (4)C4C—C5C1.410 (4)
C4A—H4A1.06 (3)C4C—H4C0.92 (3)
F1A—C6A1.342 (3)F1C—C6C1.336 (3)
F2A—C6A1.335 (3)F2C—C6C1.345 (3)
F3A—C6A1.339 (3)F3C—C6C1.334 (3)
O1A—C7A1.252 (3)O1C—C7C1.240 (3)
O2A—C7A1.233 (3)O2C—C7C1.244 (3)
C6A—C7A1.531 (4)C6C—C7C1.533 (4)
N1B—C5B1.351 (3)N1D—C5D1.349 (3)
N1B—C1B1.361 (4)N1D—C1D1.363 (3)
N1B—H1NB0.97 (3)N1D—H1ND0.92 (3)
N2B—C5B1.331 (4)N2D—C5D1.346 (4)
N2B—H2NB0.91 (3)N2D—H2ND0.95 (3)
N2B—H3NB0.86 (3)N2D—H3ND0.84 (3)
C1B—C2B1.352 (4)C1D—C2D1.345 (4)
C1B—H1B1.06 (3)C1D—H1D1.03 (3)
C2B—C3B1.396 (5)C2D—C3D1.395 (4)
C2B—H2B1.07 (3)C2D—H2D0.99 (3)
C3B—C4B1.342 (5)C3D—C4D1.353 (4)
C3B—H3B0.91 (3)C3D—H3D0.97 (3)
C4B—C5B1.426 (4)C4D—C5D1.409 (4)
C4B—H4B1.05 (3)C4D—H4D1.08 (3)
F1B—C6B1.334 (3)F1D—C6D1.340 (3)
F2B—C6B1.348 (3)F2D—C6D1.340 (3)
F3B—C6B1.343 (3)F3D—C6D1.341 (3)
O1B—C7B1.238 (3)O1D—C7D1.231 (3)
O2B—C7B1.245 (3)O2D—C7D1.253 (3)
C6B—C7B1.530 (4)C6D—C7D1.526 (4)
C5A—N1A—C1A121.9 (3)C5C—N1C—C1C123.2 (3)
C5A—N1A—H1NA113.5 (17)C5C—N1C—H1NC119 (2)
C1A—N1A—H1NA124.1 (17)C1C—N1C—H1NC118 (2)
C5A—N2A—H2NA112 (2)C5C—N2C—H2NC117 (2)
C5A—N2A—H3NA125 (2)C5C—N2C—H3NC121 (2)
H2NA—N2A—H3NA123 (3)H2NC—N2C—H3NC121 (3)
C2A—C1A—N1A121.1 (3)C2C—C1C—N1C120.4 (3)
C2A—C1A—H1A127.9 (16)C2C—C1C—H1C123.0 (16)
N1A—C1A—H1A110.7 (16)N1C—C1C—H1C116.5 (16)
C1A—C2A—C3A119.0 (3)C1C—C2C—C3C118.2 (3)
C1A—C2A—H2A120.0 (18)C1C—C2C—H2C122.2 (18)
C3A—C2A—H2A120.9 (18)C3C—C2C—H2C119.6 (18)
C4A—C3A—C2A120.1 (3)C4C—C3C—C2C121.4 (3)
C4A—C3A—H3A121.1 (17)C4C—C3C—H3C119.9 (17)
C2A—C3A—H3A118.8 (17)C2C—C3C—H3C118.7 (17)
C3A—C4A—C5A120.2 (3)C3C—C4C—C5C119.4 (3)
C3A—C4A—H4A123.7 (16)C3C—C4C—H4C121.2 (18)
C5A—C4A—H4A116.1 (16)C5C—C4C—H4C119.4 (18)
N2A—C5A—N1A118.0 (3)N2C—C5C—N1C118.5 (3)
N2A—C5A—C4A124.2 (3)N2C—C5C—C4C124.0 (3)
N1A—C5A—C4A117.8 (3)N1C—C5C—C4C117.5 (2)
F2A—C6A—F3A106.7 (2)F3C—C6C—F1C106.4 (2)
F2A—C6A—F1A106.1 (2)F3C—C6C—F2C106.2 (2)
F3A—C6A—F1A106.0 (2)F1C—C6C—F2C106.6 (2)
F2A—C6A—C7A110.6 (2)F3C—C6C—C7C113.8 (2)
F3A—C6A—C7A113.1 (2)F1C—C6C—C7C113.3 (2)
F1A—C6A—C7A113.9 (2)F2C—C6C—C7C110.0 (2)
O2A—C7A—O1A129.3 (3)O1C—C7C—O2C128.8 (3)
O2A—C7A—C6A115.3 (2)O1C—C7C—C6C115.7 (2)
O1A—C7A—C6A115.3 (2)O2C—C7C—C6C115.5 (2)
C5B—N1B—C1B122.8 (3)C5D—N1D—C1D122.2 (3)
C5B—N1B—H1NB115.4 (17)C5D—N1D—H1ND115.3 (18)
C1B—N1B—H1NB121.8 (17)C1D—N1D—H1ND122.3 (18)
C5B—N2B—H2NB126 (2)C5D—N2D—H2ND128.0 (17)
C5B—N2B—H3NB122 (2)C5D—N2D—H3ND120 (2)
H2NB—N2B—H3NB108 (3)H2ND—N2D—H3ND109 (3)
C2B—C1B—N1B120.6 (3)C2D—C1D—N1D120.6 (3)
C2B—C1B—H1B123.2 (16)C2D—C1D—H1D124.2 (15)
N1B—C1B—H1B116.0 (16)N1D—C1D—H1D115.0 (15)
C1B—C2B—C3B118.0 (3)C1D—C2D—C3D118.3 (3)
C1B—C2B—H2B117.9 (19)C1D—C2D—H2D118.3 (18)
C3B—C2B—H2B124.0 (19)C3D—C2D—H2D123.4 (18)
C4B—C3B—C2B122.0 (3)C4D—C3D—C2D121.6 (3)
C4B—C3B—H3B121 (2)C4D—C3D—H3D118.7 (17)
C2B—C3B—H3B117 (2)C2D—C3D—H3D119.6 (17)
C3B—C4B—C5B119.3 (3)C3D—C4D—C5D119.0 (3)
C3B—C4B—H4B126.8 (17)C3D—C4D—H4D124.8 (14)
C5B—C4B—H4B113.9 (17)C5D—C4D—H4D116.2 (14)
N2B—C5B—N1B117.9 (3)N2D—C5D—N1D117.9 (3)
N2B—C5B—C4B124.9 (3)N2D—C5D—C4D123.9 (3)
N1B—C5B—C4B117.3 (3)N1D—C5D—C4D118.2 (3)
F1B—C6B—F3B106.3 (2)F1D—C6D—F2D106.3 (2)
F1B—C6B—F2B106.5 (2)F1D—C6D—F3D106.4 (2)
F3B—C6B—F2B106.2 (2)F2D—C6D—F3D106.1 (2)
F1B—C6B—C7B113.6 (2)F1D—C6D—C7D113.4 (2)
F3B—C6B—C7B113.4 (2)F2D—C6D—C7D110.3 (2)
F2B—C6B—C7B110.4 (2)F3D—C6D—C7D113.8 (2)
O1B—C7B—O2B128.8 (3)O1D—C7D—O2D128.9 (3)
O1B—C7B—C6B116.1 (2)O1D—C7D—C6D114.7 (3)
O2B—C7B—C6B115.0 (2)O2D—C7D—C6D116.3 (2)
C5A—N1A—C1A—C2A0.6 (4)C5C—N1C—C1C—C2C1.1 (4)
N1A—C1A—C2A—C3A−0.9 (4)N1C—C1C—C2C—C3C−0.3 (4)
C1A—C2A—C3A—C4A0.5 (4)C1C—C2C—C3C—C4C−0.6 (5)
C2A—C3A—C4A—C5A0.2 (4)C2C—C3C—C4C—C5C0.9 (4)
C1A—N1A—C5A—N2A−178.4 (3)C1C—N1C—C5C—N2C179.2 (3)
C1A—N1A—C5A—C4A0.0 (4)C1C—N1C—C5C—C4C−0.8 (4)
C3A—C4A—C5A—N2A177.9 (3)C3C—C4C—C5C—N2C179.8 (3)
C3A—C4A—C5A—N1A−0.5 (4)C3C—C4C—C5C—N1C−0.2 (4)
F2A—C6A—C7A—O2A85.4 (3)F3C—C6C—C7C—O1C−154.3 (2)
F3A—C6A—C7A—O2A−34.1 (3)F1C—C6C—C7C—O1C−32.5 (3)
F1A—C6A—C7A—O2A−155.3 (2)F2C—C6C—C7C—O1C86.7 (3)
F2A—C6A—C7A—O1A−92.0 (3)F3C—C6C—C7C—O2C28.9 (3)
F3A—C6A—C7A—O1A148.5 (2)F1C—C6C—C7C—O2C150.7 (2)
F1A—C6A—C7A—O1A27.4 (3)F2C—C6C—C7C—O2C−90.2 (3)
C5B—N1B—C1B—C2B−1.3 (4)C5D—N1D—C1D—C2D0.5 (4)
N1B—C1B—C2B—C3B0.5 (5)N1D—C1D—C2D—C3D−0.7 (4)
C1B—C2B—C3B—C4B0.7 (5)C1D—C2D—C3D—C4D0.3 (5)
C2B—C3B—C4B—C5B−1.3 (5)C2D—C3D—C4D—C5D0.2 (4)
C1B—N1B—C5B—N2B−179.4 (3)C1D—N1D—C5D—N2D178.9 (3)
C1B—N1B—C5B—C4B0.7 (4)C1D—N1D—C5D—C4D0.0 (4)
C3B—C4B—C5B—N2B−179.3 (3)C3D—C4D—C5D—N2D−179.1 (3)
C3B—C4B—C5B—N1B0.5 (4)C3D—C4D—C5D—N1D−0.4 (4)
F1B—C6B—C7B—O1B31.0 (3)F1D—C6D—C7D—O1D37.8 (4)
F3B—C6B—C7B—O1B152.5 (2)F2D—C6D—C7D—O1D−81.4 (3)
F2B—C6B—C7B—O1B−88.5 (3)F3D—C6D—C7D—O1D159.6 (3)
F1B—C6B—C7B—O2B−151.5 (2)F1D—C6D—C7D—O2D−144.0 (3)
F3B—C6B—C7B—O2B−30.0 (3)F2D—C6D—C7D—O2D96.8 (3)
F2B—C6B—C7B—O2B89.0 (3)F3D—C6D—C7D—O2D−22.2 (4)
D—H···AD—HH···AD···AD—H···A
N1A—H1NA···O2Di0.92 (3)1.91 (3)2.809 (3)168 (2)
N2A—H2NA···O1Di1.02 (4)1.79 (4)2.795 (4)169 (4)
N2A—H3NA···O1Aii0.84 (3)2.10 (3)2.899 (3)160 (3)
N1B—H1NB···O2Ciii0.97 (3)1.75 (3)2.704 (3)166 (3)
N2B—H2NB···O1Ciii0.91 (4)2.01 (4)2.892 (4)164 (3)
N2B—H3NB···O2Biii0.86 (3)2.07 (3)2.858 (3)154 (3)
N1C—H1NC···O1Aiv0.86 (3)1.94 (3)2.789 (3)172 (3)
N2C—H2NC···O2Aiv0.90 (3)1.93 (3)2.827 (4)177 (3)
N2C—H3NC···O2Dv0.94 (3)2.04 (3)2.894 (3)150 (3)
N1D—H1ND···O2Bvi0.92 (3)1.80 (3)2.701 (3)164 (2)
N2D—H2ND···O1Bvi0.95 (3)1.97 (3)2.878 (4)160 (2)
N2D—H3ND···O2Cvii0.84 (3)2.21 (3)2.908 (3)141 (3)
C1A—H1A···O2A1.00 (3)2.20 (3)3.141 (3)155 (2)
C1B—H1B···F3Cviii1.06 (3)2.43 (3)3.288 (4)137 (2)
C1C—H1C···O1Dix0.95 (2)2.21 (2)3.107 (3)158 (2)
C4A—H4A···F1Aii1.06 (3)2.34 (3)3.352 (3)159 (2)
C4B—H4B···O1C1.05 (3)2.25 (3)3.294 (4)171 (2)
C4C—H4C···F3Dv0.93 (3)2.50 (3)3.365 (3)155 (3)
C4D—H4D···O1Bii1.08 (2)2.18 (2)3.204 (4)159 (2)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1A—H1NA⋯O2Di0.92 (3)1.91 (3)2.809 (3)168 (2)
N2A—H2NA⋯O1Di1.02 (4)1.79 (4)2.795 (4)169 (4)
N2A—H3NA⋯O1Aii0.84 (3)2.10 (3)2.899 (3)160 (3)
N1B—H1NB⋯O2Ciii0.97 (3)1.75 (3)2.704 (3)166 (3)
N2B—H2NB⋯O1Ciii0.91 (4)2.01 (4)2.892 (4)164 (3)
N2B—H3NB⋯O2Biii0.86 (3)2.07 (3)2.858 (3)154 (3)
N1C—H1NC⋯O1Aiv0.86 (3)1.94 (3)2.789 (3)172 (3)
N2C—H2NC⋯O2Aiv0.90 (3)1.93 (3)2.827 (4)177 (3)
N2C—H3NC⋯O2Dv0.94 (3)2.04 (3)2.894 (3)150 (3)
N1D—H1ND⋯O2Bvi0.92 (3)1.80 (3)2.701 (3)164 (2)
N2D—H2ND⋯O1Bvi0.95 (3)1.97 (3)2.878 (4)160 (2)
N2D—H3ND⋯O2Cvii0.84 (3)2.21 (3)2.908 (3)141 (3)
C1A—H1A⋯O2A1.00 (3)2.20 (3)3.141 (3)155 (2)
C1B—H1B⋯F3Cviii1.06 (3)2.43 (3)3.288 (4)137 (2)
C1C—H1C⋯O1Dix0.95 (2)2.21 (2)3.107 (3)158 (2)
C4A—H4A⋯F1Aii1.06 (3)2.34 (3)3.352 (3)159 (2)
C4B—H4B⋯O1C1.05 (3)2.25 (3)3.294 (4)171 (2)
C4C—H4C⋯F3Dv0.93 (3)2.50 (3)3.365 (3)155 (3)
C4D—H4D⋯O1Bii1.08 (2)2.18 (2)3.204 (4)159 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) .

  4 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  2-Aminopyridinium salicylate.

Authors:  R W Gellert; I N Hsu
Journal:  Acta Crystallogr C       Date:  1988-02-15       Impact factor: 1.172

3.  A second polymorph of 2-aminopyridinium dihydrogenphosphate.

Authors:  Selcuk Demir; Veysel T Yilmaz; William T A Harrison
Journal:  Acta Crystallogr C       Date:  2005-08-31       Impact factor: 1.172

4.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  4 in total
  2 in total

1.  2-Amino-4-methyl-pyridinium trifluoro-acetate: a monoclinic polymorph.

Authors:  Mehrdad Pourayoubi; Maryam Toghraee; Arnold L Rheingold; James A Golen
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-03-17

2.  2-Amino-pyridinium 2-meth-oxy-carbonyl-4,6-dinitro-phenolate.

Authors:  Dong-Liang Wu; Zi-Jing Xiao
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-12-14
  2 in total

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