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The essentially planar 2,6-bis­(2-pyridylamino)pyridinium cation, as well as the perchlorate anion, occupy special positions on twofold axes in the structure of the title compound, C15H14N5+·ClO4-. The central pyridine ring is protonated and the pyridinium H atom forms two intra­molecular hydrogen bonds, thus closing two hydrogen-bonded six-membered pseudocycles. The secondary amino group participates in the hydrogen bonding with one of the O atoms of a neighboring perchlorate anion; these hydrogen bonds link cations and anions into infinite chains running along the a axis of the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043984/ya2027sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043984/ya2027Isup2.hkl
Contains datablock I

CCDC reference: 628438

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.051
  • wR factor = 0.158
  • Data-to-parameter ratio = 10.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 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 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker,1998); 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: SHELXTL(Bruker, 1998); software used to prepare material for publication: SHELXTL.

2,6-Bis(2-pyridylamino)pyridinium perchlorate top
Crystal data top
C15H14N5+·ClO4F(000) = 752
Mr = 363.76Dx = 1.542 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 10.656 (2) ÅCell parameters from 1056 reflections
b = 19.538 (5) Åθ = 4.9–26.9°
c = 7.8160 (15) ŵ = 0.28 mm1
β = 105.624 (3)°T = 273 K
V = 1567.2 (6) Å3Block, green
Z = 40.40 × 0.36 × 0.30 mm
Data collection top
Bruker SMART CCD
diffractometer
1466 independent reflections
Radiation source: fine-focus sealed tube1050 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
φ and ω scansθmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1112
Tmin = 0.897, Tmax = 0.921k = 2316
4051 measured reflectionsl = 99
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158All H-atom parameters refined
S = 0.91 w = 1/[σ2(Fo2) + (0.1091P)2]
where P = (Fo2 + 2Fc2)/3
1466 reflections(Δ/σ)max < 0.001
144 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.33 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
N10.87175 (19)1.03612 (10)0.8096 (3)0.0558 (6)
N20.8115 (2)0.92388 (11)0.8504 (3)0.0578 (6)
N31.00000.92245 (15)0.75000.0476 (7)
C10.8466 (3)1.10354 (15)0.8142 (4)0.0637 (7)
C20.7427 (3)1.12958 (17)0.8615 (4)0.0691 (8)
C30.6568 (3)1.08483 (17)0.9053 (4)0.0703 (8)
C40.6793 (3)1.01603 (17)0.9009 (4)0.0640 (7)
C50.7886 (2)0.99339 (13)0.8530 (3)0.0514 (6)
C60.9067 (2)0.88815 (12)0.8018 (3)0.0503 (6)
C70.9059 (3)0.81721 (14)0.8042 (4)0.0628 (7)
C81.00000.7827 (2)0.75000.0681 (11)
Cl11.00000.69038 (4)0.25000.0659 (4)
O10.9247 (3)0.65011 (19)0.1122 (5)0.1632 (16)
O21.0853 (3)0.72839 (18)0.1804 (4)0.1422 (13)
H10.905 (3)1.1323 (17)0.784 (4)0.082 (9)*
H210.763 (3)0.8970 (17)0.876 (4)0.083 (11)*
H40.630 (3)0.9849 (14)0.924 (4)0.062 (8)*
H20.726 (3)1.1762 (19)0.877 (4)0.096 (11)*
H30.578 (3)1.0959 (14)0.939 (4)0.074 (8)*
H70.846 (3)0.7971 (15)0.846 (4)0.077 (9)*
H81.00000.734 (3)0.75000.085 (13)*
H311.00000.965 (2)0.75000.098 (17)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0535 (11)0.0551 (13)0.0596 (13)0.0016 (9)0.0168 (10)0.0028 (9)
N20.0553 (12)0.0549 (13)0.0683 (14)0.0064 (10)0.0253 (10)0.0019 (10)
N30.0497 (15)0.0433 (15)0.0493 (15)0.0000.0123 (12)0.000
C10.0651 (16)0.0561 (16)0.0712 (17)0.0010 (13)0.0205 (13)0.0019 (13)
C20.0688 (17)0.0637 (18)0.0727 (18)0.0140 (14)0.0152 (14)0.0036 (14)
C30.0583 (16)0.082 (2)0.0707 (18)0.0139 (15)0.0178 (13)0.0104 (15)
C40.0548 (15)0.0755 (19)0.0656 (16)0.0012 (14)0.0230 (12)0.0071 (14)
C50.0489 (12)0.0584 (14)0.0451 (12)0.0008 (11)0.0094 (9)0.0028 (11)
C60.0467 (12)0.0505 (13)0.0513 (13)0.0026 (10)0.0089 (10)0.0000 (10)
C70.0525 (14)0.0519 (15)0.0820 (19)0.0083 (12)0.0148 (13)0.0045 (13)
C80.057 (2)0.047 (2)0.093 (3)0.0000.0079 (19)0.000
Cl10.0598 (6)0.0456 (5)0.0976 (8)0.0000.0302 (5)0.000
O10.137 (2)0.186 (3)0.201 (3)0.094 (2)0.106 (2)0.124 (3)
O20.0974 (18)0.136 (2)0.182 (3)0.0443 (17)0.0199 (18)0.073 (2)
Geometric parameters (Å, º) top
N1—C51.326 (3)C3—H30.97 (3)
N1—C11.347 (3)C4—C51.389 (3)
N2—C61.366 (3)C4—H40.85 (3)
N2—C51.381 (3)C6—C71.386 (4)
N2—H210.80 (3)C7—C81.367 (3)
N3—C6i1.349 (3)C7—H70.89 (3)
N3—C61.349 (3)C8—C7i1.367 (4)
N3—H310.84 (5)C8—H80.94 (5)
C1—C21.357 (4)Cl1—O21.393 (2)
C1—H10.92 (3)Cl1—O2ii1.393 (2)
C2—C31.374 (4)Cl1—O11.399 (3)
C2—H20.94 (4)Cl1—O1ii1.399 (3)
C3—C41.368 (4)
C5—N1—C1117.2 (2)N1—C5—N2118.8 (2)
C6—N2—C5130.9 (2)N1—C5—C4122.4 (2)
C6—N2—H21108 (2)N2—C5—C4118.8 (2)
C5—N2—H21121 (2)N3—C6—N2119.5 (2)
C6i—N3—C6120.4 (3)N3—C6—C7120.6 (2)
C6i—N3—H31119.79 (14)N2—C6—C7120.0 (2)
C6—N3—H31119.79 (15)C8—C7—C6118.8 (3)
N1—C1—C2123.8 (3)C8—C7—H7124 (2)
N1—C1—H1116 (2)C6—C7—H7117 (2)
C2—C1—H1120 (2)C7—C8—C7i120.9 (4)
C1—C2—C3118.5 (3)C7—C8—H8119.55 (18)
C1—C2—H2126 (2)C7i—C8—H8119.55 (19)
C3—C2—H2115 (2)O2—Cl1—O2ii115.6 (3)
C4—C3—C2119.1 (3)O2—Cl1—O1107.3 (2)
C4—C3—H3113.4 (17)O2ii—Cl1—O1107.55 (18)
C2—C3—H3127.5 (17)O2—Cl1—O1ii107.55 (18)
C3—C4—C5119.1 (3)O2ii—Cl1—O1ii107.3 (2)
C3—C4—H4125.1 (19)O1—Cl1—O1ii111.5 (4)
C5—C4—H4115.8 (18)
Symmetry codes: (i) x+2, y, z+3/2; (ii) x+2, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H31···N10.84 (5)2.08 (3)2.713 (3)132 (1)
N2—H21···O1iii0.80 (3)2.22 (3)2.985 (3)159 (3)
Symmetry code: (iii) x+3/2, y+3/2, z+1.
 

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