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In the title compound, C5H7N2+·C7H4NO4, the asymmetric unit consists of an aminopyridinium cation and a p-nitro­benzoate anion, with proton transfer occurring to the aromatic N atom of the 2-amino­pyridine molecule. In the crystal structure, the two ions are inter­connected by N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806015042/at2030sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806015042/at2030Isup2.hkl
Contains datablock I

CCDC reference: 610684

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.053
  • wR factor = 0.129
  • Data-to-parameter ratio = 8.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.58 From the CIF: _reflns_number_total 1463 Count of symmetry unique reflns 1481 Completeness (_total/calc) 98.78% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

2-aminopyridinium p-nitrobenzoate top
Crystal data top
C5H7N2+·C7H4NO4F(000) = 272
Mr = 261.24Dx = 1.471 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 25 reflections
a = 7.9403 (12) Åθ = 1–27.5°
b = 6.7719 (6) ŵ = 0.11 mm1
c = 11.1120 (15) ÅT = 120 K
β = 99.272 (6)°Block, colourless
V = 589.70 (13) Å30.3 × 0.13 × 0.06 mm
Z = 2
Data collection top
Nonius KappaCCD?
diffractometer
Rint = 0.071
φ and ω scansθmax = 27.6°, θmin = 1.9°
7208 measured reflectionsh = 1010
1463 independent reflectionsk = 88
1035 reflections with I > 2σ(I)l = 1412
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0674P)2 + 0.0892P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.053(Δ/σ)max = 0.036
wR(F2) = 0.129Δρmax = 0.38 e Å3
S = 1.05Δρmin = 0.31 e Å3
1463 reflectionsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
173 parametersExtinction coefficient: 0.041 (11)
1 restraint
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
O10.6522 (3)0.2889 (3)0.6912 (2)0.0293 (6)
O41.0654 (3)1.2352 (4)0.8212 (2)0.0370 (7)
O31.0612 (4)1.1706 (4)0.6299 (2)0.0405 (7)
C100.8234 (4)0.6394 (5)0.6599 (3)0.0255 (8)
H100.79880.5540.59390.031*
C110.9026 (4)0.8193 (5)0.6455 (3)0.0253 (8)
H110.93010.85630.57050.03*
O20.6600 (3)0.3487 (4)0.8896 (2)0.0331 (6)
C90.7809 (5)0.5866 (5)0.7717 (3)0.0235 (8)
C60.9391 (4)0.9408 (5)0.7455 (3)0.0251 (8)
C130.6911 (4)0.3931 (5)0.7860 (3)0.0247 (8)
C80.8216 (4)0.7131 (5)0.8708 (3)0.0259 (8)
H80.79540.67680.94640.031*
N31.0270 (4)1.1284 (5)0.7315 (3)0.0297 (7)
C10.4211 (4)0.8976 (5)0.8091 (3)0.0247 (8)
C20.3281 (4)0.7180 (5)0.8080 (3)0.0291 (9)
H20.29660.66980.87960.035*
C30.2853 (4)0.6168 (5)0.7012 (3)0.0297 (9)
H30.2250.49890.70040.036*
C40.3311 (4)0.6887 (6)0.5932 (3)0.0315 (9)
H40.29930.62180.520.038*
C50.4231 (4)0.8582 (6)0.5973 (3)0.0276 (8)
H50.45620.9060.52620.033*
N10.4676 (4)0.9593 (4)0.7034 (3)0.0246 (7)
H10.52711.06540.70330.029*
N20.4648 (4)1.0073 (5)0.9079 (3)0.0321 (8)
H2A0.52131.11470.90380.039*
H2B0.43660.97110.97610.039*
C70.9001 (5)0.8916 (5)0.8583 (3)0.0277 (8)
H70.92610.97680.92430.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0408 (15)0.0254 (13)0.0224 (13)0.0070 (11)0.0074 (11)0.0012 (11)
O40.0462 (17)0.0297 (15)0.0337 (16)0.0081 (13)0.0025 (12)0.0040 (13)
O30.0543 (18)0.0381 (16)0.0326 (15)0.0129 (14)0.0173 (13)0.0039 (13)
C100.029 (2)0.0260 (19)0.0205 (19)0.0041 (16)0.0006 (15)0.0007 (17)
C110.0270 (19)0.026 (2)0.0236 (18)0.0008 (15)0.0052 (15)0.0032 (15)
O20.0473 (15)0.0272 (15)0.0270 (13)0.0057 (12)0.0131 (11)0.0008 (11)
C90.0265 (18)0.0219 (18)0.0223 (18)0.0019 (15)0.0041 (14)0.0014 (14)
C60.0231 (18)0.0210 (18)0.031 (2)0.0003 (14)0.0056 (15)0.0014 (16)
C130.0281 (19)0.0210 (19)0.026 (2)0.0000 (15)0.0072 (15)0.0011 (15)
C80.032 (2)0.027 (2)0.0188 (18)0.0016 (16)0.0059 (15)0.0001 (15)
N30.0293 (17)0.0255 (17)0.0340 (19)0.0028 (14)0.0044 (14)0.0011 (15)
C10.0220 (18)0.027 (2)0.0253 (19)0.0023 (15)0.0040 (15)0.0021 (16)
C20.030 (2)0.028 (2)0.030 (2)0.0027 (18)0.0074 (16)0.0050 (17)
C30.027 (2)0.023 (2)0.038 (2)0.0028 (17)0.0034 (17)0.0007 (17)
C40.0281 (19)0.036 (2)0.030 (2)0.0008 (17)0.0019 (16)0.0070 (17)
C50.0308 (19)0.029 (2)0.0221 (18)0.0013 (17)0.0027 (15)0.0019 (16)
N10.0282 (16)0.0215 (15)0.0243 (16)0.0027 (13)0.0053 (12)0.0013 (13)
N20.046 (2)0.0284 (18)0.0239 (16)0.0055 (15)0.0102 (14)0.0014 (13)
C70.031 (2)0.023 (2)0.0292 (19)0.0025 (16)0.0052 (16)0.0027 (16)
Geometric parameters (Å, º) top
O1—C131.264 (4)C1—N21.324 (4)
O4—N31.230 (4)C1—N11.353 (4)
O3—N31.236 (4)C1—C21.422 (5)
C10—C111.392 (5)C2—C31.365 (5)
C10—C91.386 (5)C2—H20.93
C10—H100.93C3—C41.396 (5)
C11—C61.376 (5)C3—H30.93
C11—H110.93C4—C51.357 (5)
O2—C131.253 (4)C4—H40.93
C9—C81.392 (5)C5—N11.360 (4)
C9—C131.512 (5)C5—H50.93
C6—C71.379 (5)N1—H10.86
C6—N31.470 (5)N2—H2A0.86
C8—C71.377 (5)N2—H2B0.86
C8—H80.93C7—H70.93
C11—C10—C9120.6 (3)N1—C1—C2118.1 (3)
C11—C10—H10119.7C3—C2—C1119.5 (3)
C9—C10—H10119.7C3—C2—H2120.2
C6—C11—C10118.1 (3)C1—C2—H2120.2
C6—C11—H11121C2—C3—C4120.6 (3)
C10—C11—H11121C2—C3—H3119.7
C10—C9—C8119.4 (3)C4—C3—H3119.7
C10—C9—C13120.3 (3)C5—C4—C3118.7 (3)
C8—C9—C13120.3 (3)C5—C4—H4120.7
C11—C6—C7122.7 (3)C3—C4—H4120.7
C11—C6—N3118.2 (3)C4—C5—N1121.2 (3)
C7—C6—N3119.1 (3)C4—C5—H5119.4
O1—C13—O2125.0 (3)N1—C5—H5119.4
O1—C13—C9116.9 (3)C1—N1—C5121.9 (3)
O2—C13—C9118.1 (3)C1—N1—H1119.1
C7—C8—C9120.8 (3)C5—N1—H1119.1
C7—C8—H8119.6C1—N2—H2A120
C9—C8—H8119.6C1—N2—H2B120
O4—N3—O3122.8 (3)H2A—N2—H2B120
O4—N3—C6118.8 (3)C8—C7—C6118.4 (3)
O3—N3—C6118.4 (3)C8—C7—H7120.8
N2—C1—N1118.3 (3)C6—C7—H7120.8
N2—C1—C2123.6 (3)
C9—C10—C11—C60.9 (5)C11—C6—N3—O31.4 (5)
C11—C10—C9—C81.5 (5)C7—C6—N3—O3180.0 (3)
C11—C10—C9—C13178.6 (3)N2—C1—C2—C3178.5 (3)
C10—C11—C6—C70.2 (5)N1—C1—C2—C31.6 (5)
C10—C11—C6—N3178.4 (3)C1—C2—C3—C40.4 (5)
C10—C9—C13—O12.6 (5)C2—C3—C4—C51.8 (5)
C8—C9—C13—O1177.4 (3)C3—C4—C5—N11.2 (5)
C10—C9—C13—O2177.8 (3)N2—C1—N1—C5177.9 (3)
C8—C9—C13—O22.2 (5)C2—C1—N1—C52.2 (5)
C10—C9—C8—C71.4 (5)C4—C5—N1—C10.8 (5)
C13—C9—C8—C7178.6 (3)C9—C8—C7—C60.7 (5)
C11—C6—N3—O4177.6 (3)C11—C6—C7—C80.1 (5)
C7—C6—N3—O41.0 (5)N3—C6—C7—C8178.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.861.832.686 (4)176
N2—H2A···O2i0.861.952.809 (4)176
N2—H2B···O2ii0.861.972.814 (4)168
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1/2, z+2.
 

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