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The amino group in the 3 position of the title compound, C5H7N3, is significantly displaced out of the plane of the heteroaromatic ring. Hydrogen bonds between the amino groups and the pyridine N atom link neighbouring mol­ecules into chains along the crystallographic c axis in a similar manner to that in 4-amino­pyridine. Additional hydrogen bonds lead to the formation of a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807001444/bt2244sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807001444/bt2244Isup2.hkl
Contains datablock I

CCDC reference: 636852

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.081
  • Data-to-parameter ratio = 8.4

checkCIF/PLATON results

No syntax errors found



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 25.88 From the CIF: _reflns_number_total 614 Count of symmetry unique reflns 614 Completeness (_total/calc) 100.00% 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 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 0 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

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); 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.

3,4-diaminopyridine top
Crystal data top
C5H7N3Dx = 1.404 Mg m3
Mr = 109.13Melting point = 216–218 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 579 reflections
a = 5.5815 (18) Åθ = 3.2–21.6°
b = 7.352 (2) ŵ = 0.09 mm1
c = 12.579 (4) ÅT = 120 K
V = 516.2 (3) Å3Platelet, yellow
Z = 40.20 × 0.15 × 0.02 mm
F(000) = 232
Data collection top
Bruker SMART CCD area-detector
diffractometer
562 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.057
Graphite monochromatorθmax = 25.9°, θmin = 3.2°
ω scansh = 66
5342 measured reflectionsk = 99
614 independent reflectionsl = 1515
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)] = 0.036Hydrogen site location: difference Fourier map
wR(F2) = 0.081H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.03P)2 + 0.2P]
where P = (Fo2 + 2Fc2)/3
614 reflections(Δ/σ)max < 0.001
73 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.13 e Å3
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
xyzUiso*/Ueq
N10.3611 (4)0.0405 (3)0.07697 (14)0.0174 (5)
N20.1059 (4)0.1199 (3)0.19043 (15)0.0179 (5)
H2A0.03230.16710.16600.021*
H2B0.08600.04570.24660.021*
N30.5142 (4)0.0869 (3)0.24078 (16)0.0232 (5)
H3A0.39810.07060.28950.028*
H3B0.63130.16910.25110.028*
C20.2151 (4)0.0877 (3)0.00339 (18)0.0162 (5)
H20.07210.15080.01440.019*
C30.2559 (4)0.0521 (3)0.10995 (17)0.0138 (5)
C40.4643 (4)0.0466 (3)0.13767 (18)0.0165 (5)
C50.6169 (4)0.0952 (3)0.05459 (18)0.0175 (5)
H50.76020.16020.06930.021*
C60.5607 (4)0.0493 (3)0.04904 (18)0.0182 (5)
H60.66960.08330.10360.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0197 (11)0.0162 (9)0.0163 (10)0.0012 (9)0.0006 (8)0.0005 (8)
N20.0183 (10)0.0209 (10)0.0143 (10)0.0038 (8)0.0006 (9)0.0021 (8)
N30.0244 (11)0.0277 (11)0.0174 (10)0.0095 (10)0.0000 (9)0.0030 (9)
C20.0145 (12)0.0139 (11)0.0202 (11)0.0005 (9)0.0033 (10)0.0007 (9)
C30.0139 (11)0.0112 (10)0.0164 (11)0.0038 (10)0.0013 (10)0.0021 (9)
C40.0204 (12)0.0113 (10)0.0179 (11)0.0024 (10)0.0020 (10)0.0004 (9)
C50.0140 (11)0.0151 (11)0.0233 (12)0.0004 (10)0.0006 (11)0.0000 (10)
C60.0168 (13)0.0188 (12)0.0190 (12)0.0000 (10)0.0038 (10)0.0024 (11)
Geometric parameters (Å, º) top
N1—C61.342 (3)C2—C31.385 (3)
N1—C21.344 (3)C2—H20.9500
N2—C31.405 (3)C3—C41.415 (3)
N2—H2A0.9000C4—C51.395 (3)
N2—H2B0.9000C5—C61.383 (3)
N3—C41.359 (3)C5—H50.9500
N3—H3A0.9000C6—H60.9500
N3—H3B0.9000
C6—N1—C2115.69 (19)C2—C3—C4118.1 (2)
C3—N2—H2A113.6N2—C3—C4119.63 (19)
C3—N2—H2B115.1N3—C4—C5122.3 (2)
H2A—N2—H2B113.4N3—C4—C3121.0 (2)
C4—N3—H3A118.3C5—C4—C3116.7 (2)
C4—N3—H3B115.7C6—C5—C4120.4 (2)
H3A—N3—H3B120.9C6—C5—H5119.8
N1—C2—C3125.4 (2)C4—C5—H5119.8
N1—C2—H2117.3N1—C6—C5123.7 (2)
C3—C2—H2117.3N1—C6—H6118.1
C2—C3—N2122.2 (2)C5—C6—H6118.1
C6—N1—C2—C30.4 (3)N2—C3—C4—C5174.1 (2)
N1—C2—C3—N2174.1 (2)N3—C4—C5—C6179.1 (2)
N1—C2—C3—C41.9 (3)C3—C4—C5—C60.8 (3)
C2—C3—C4—N3179.7 (2)C2—N1—C6—C51.0 (3)
N2—C3—C4—N34.2 (3)C4—C5—C6—N10.7 (4)
C2—C3—C4—C52.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N1i0.902.503.184 (3)134
N2—H2B···N1ii0.902.333.160 (3)154
N3—H3A···N20.902.482.812 (3)102
N3—H3A···N1ii0.902.233.124 (3)174
N3—H3B···N2iii0.902.263.145 (3)169
Symmetry codes: (i) x1/2, y1/2, z; (ii) x+1/2, y, z+1/2; (iii) x+1, y+1/2, z+1/2.
 

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