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The title compound, C12H14N3+·ClO4, crystallizes from a solution of bis(2-pyridyl­methyl)­amine and HClO4 in water/DMF (3:1, v/v) with the secondary amine N atom protonated. The two pyridine arms of the ligand are held in a closed conformation through a strong bifurcated hydrogen bond from one of the ammonium H atoms. The ClO4 anion is also hydrogen bonded to the same H atom of the ammonium N atom, with an N...O distance of 2.899 (4) Å. The other ammonium H atom is hydrogen bonded to an O atom of a symmetry-related perchlorate anion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802012527/cf6188sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802012527/cf6188Isup2.hkl
Contains datablock I

CCDC reference: 193748

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in solvent or counterion
  • R factor = 0.055
  • wR factor = 0.156
  • Data-to-parameter ratio = 9.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_302 Alert C Anion/Solvent Disorder ....................... 24.00 Perc. PLAT_420 Alert C D-H Without Acceptor N - H1N ? PLAT_420 Alert C D-H Without Acceptor N - H2N ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

bis(2-pyridylmethyl)ammonium perchlorate top
Crystal data top
C12H14N3+·ClO4Dx = 1.428 Mg m3
Mr = 299.71Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 26 reflections
a = 11.3201 (18) Åθ = 11.6–13.0°
b = 14.422 (2) ŵ = 0.29 mm1
c = 17.073 (3) ÅT = 293 K
V = 2787.3 (7) Å3Plate, pale yellow
Z = 80.84 × 0.56 × 0.10 mm
F(000) = 1248
Data collection top
Siemens P4S
diffractometer
1676 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 25.0°, θmin = 2.6°
2θ/ω scansh = 130
Absorption correction: part of the refinement model (ΔF)
(SHELXTL; Sheldrick, 1997)
k = 170
Tmin = 0.728, Tmax = 0.971l = 200
2448 measured reflections3 standard reflections every 97 reflections
2448 independent reflections intensity decay: 1.0%
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.065P)2 + 2.1051P]
where P = (Fo2 + 2Fc2)/3
2448 reflections(Δ/σ)max = 0.001
250 parametersΔρmax = 0.24 e Å3
58 restraintsΔρmin = 0.27 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*/UeqOcc. (<1)
Cl0.38743 (7)0.11220 (6)0.08135 (5)0.0592 (3)
O1A0.4293 (8)0.1513 (6)0.0094 (3)0.085 (3)0.47
O2A0.3456 (7)0.1850 (5)0.1313 (5)0.095 (3)0.47
O3A0.2926 (5)0.0494 (5)0.0651 (5)0.066 (2)0.47
O4A0.4814 (6)0.0637 (6)0.1193 (5)0.130 (9)0.47
O1B0.3085 (7)0.1575 (8)0.1347 (6)0.101 (6)0.29
O2B0.3281 (8)0.0355 (7)0.0455 (8)0.080 (5)0.29
O3B0.4236 (13)0.1766 (7)0.0222 (6)0.104 (6)0.29
O4B0.4888 (8)0.0796 (9)0.1231 (7)0.056 (4)0.29
O1C0.3846 (18)0.1955 (7)0.1269 (9)0.100 (10)*0.14
O2C0.4892 (10)0.0588 (12)0.1024 (11)0.066 (10)*0.14
O3C0.2829 (10)0.0592 (12)0.0962 (10)0.083 (10)*0.14
O4C0.3930 (15)0.1353 (13)0.0001 (3)0.056 (6)*0.14
O1D0.4179 (19)0.2072 (4)0.0950 (12)0.097 (11)*0.10
O2D0.4198 (18)0.0870 (14)0.0031 (4)0.060 (7)*0.10
O3D0.4493 (17)0.0544 (11)0.1358 (8)0.041 (7)*0.10
O4D0.2628 (4)0.1002 (16)0.0914 (12)0.16 (2)*0.10
N0.2353 (2)0.35208 (19)0.07550 (13)0.0523 (7)
H1N0.25520.41220.08090.063*
H2N0.29770.31790.09080.063*
N1A0.4140 (3)0.3867 (2)0.02112 (16)0.0605 (8)
N1B0.2690 (2)0.3938 (2)0.22490 (16)0.0611 (8)
C1A0.5074 (4)0.4094 (2)0.0653 (2)0.0693 (10)
H1AA0.57590.42850.03990.083*
C2A0.5084 (4)0.4063 (3)0.1443 (3)0.0792 (12)
H2AA0.57540.42320.17240.095*
C3A0.4074 (5)0.3774 (3)0.1824 (2)0.0863 (14)
H3AA0.40510.37440.23680.104*
C4A0.3095 (4)0.3529 (3)0.1386 (2)0.0707 (11)
H4AA0.24040.33300.16280.085*
C5A0.3166 (3)0.3585 (2)0.05823 (19)0.0547 (8)
C6A0.2128 (3)0.3336 (3)0.00790 (19)0.0702 (11)
H6AA0.14450.36900.02470.084*
H6AB0.19470.26830.01470.084*
C1B0.2940 (4)0.4151 (3)0.2995 (2)0.0710 (11)
H1BA0.36700.44180.31020.085*
C2B0.2187 (4)0.4000 (3)0.3608 (2)0.0729 (11)
H2BA0.23990.41680.41150.088*
C3B0.1119 (4)0.3598 (3)0.3461 (2)0.0725 (11)
H3BA0.05900.34860.38670.087*
C4B0.0839 (3)0.3361 (3)0.2706 (2)0.0635 (10)
H4BA0.01190.30810.25910.076*
C5B0.1643 (3)0.3546 (2)0.21190 (18)0.0511 (8)
C6B0.1354 (3)0.3320 (3)0.12818 (19)0.0640 (10)
H6BA0.11490.26690.12410.077*
H6BB0.06730.36800.11190.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0588 (5)0.0616 (5)0.0571 (5)0.0029 (4)0.0055 (4)0.0037 (4)
O1A0.071 (5)0.115 (7)0.070 (5)0.044 (5)0.010 (4)0.025 (4)
O2A0.155 (8)0.058 (4)0.073 (5)0.029 (5)0.028 (5)0.018 (3)
O3A0.038 (3)0.064 (5)0.096 (7)0.007 (3)0.019 (4)0.000 (4)
O4A0.069 (9)0.213 (18)0.109 (11)0.047 (8)0.005 (8)0.050 (9)
O1B0.045 (5)0.140 (14)0.119 (11)0.026 (7)0.008 (6)0.065 (10)
O2B0.094 (11)0.069 (7)0.078 (8)0.021 (8)0.005 (8)0.021 (6)
O3B0.130 (14)0.060 (7)0.123 (13)0.012 (8)0.007 (11)0.048 (8)
O4B0.049 (8)0.069 (7)0.051 (7)0.013 (6)0.003 (6)0.007 (6)
N0.0535 (15)0.0570 (15)0.0464 (14)0.0047 (13)0.0030 (12)0.0015 (12)
N1A0.0644 (18)0.0656 (18)0.0516 (16)0.0069 (15)0.0017 (14)0.0036 (14)
N1B0.0536 (17)0.0740 (19)0.0558 (16)0.0035 (15)0.0041 (13)0.0099 (14)
C1A0.071 (2)0.063 (2)0.074 (3)0.0033 (19)0.015 (2)0.0041 (19)
C2A0.100 (3)0.067 (3)0.071 (3)0.007 (2)0.026 (3)0.007 (2)
C3A0.139 (4)0.076 (3)0.044 (2)0.021 (3)0.019 (3)0.0066 (19)
C4A0.099 (3)0.070 (2)0.0428 (19)0.001 (2)0.007 (2)0.0003 (17)
C5A0.068 (2)0.0519 (18)0.0438 (17)0.0012 (17)0.0023 (16)0.0013 (14)
C6A0.070 (2)0.095 (3)0.0457 (19)0.018 (2)0.0086 (17)0.0031 (19)
C1B0.070 (2)0.075 (2)0.068 (2)0.006 (2)0.018 (2)0.015 (2)
C2B0.098 (3)0.073 (2)0.048 (2)0.027 (2)0.009 (2)0.0081 (18)
C3B0.081 (3)0.080 (3)0.057 (2)0.016 (2)0.010 (2)0.004 (2)
C4B0.060 (2)0.071 (2)0.059 (2)0.0053 (18)0.0058 (17)0.0081 (18)
C5B0.0487 (18)0.0545 (18)0.0501 (19)0.0049 (16)0.0036 (15)0.0014 (15)
C6B0.055 (2)0.085 (3)0.053 (2)0.0198 (19)0.0002 (16)0.0017 (18)
Geometric parameters (Å, º) top
Cl—O1A1.432 (2)N1B—C1B1.340 (4)
Cl—O2A1.433 (2)C1A—C2A1.350 (6)
Cl—O3A1.432 (2)C1A—H1AA0.930
Cl—O4A1.429 (2)C2A—C3A1.380 (6)
Cl—O1B1.433 (2)C2A—H2AA0.930
Cl—O2B1.431 (2)C3A—C4A1.383 (6)
Cl—O3B1.432 (2)C3A—H3AA0.930
Cl—O4B1.430 (2)C4A—C5A1.376 (5)
Cl—O1C1.432 (2)C4A—H4AA0.930
Cl—O2C1.431 (2)C5A—C6A1.500 (5)
Cl—O3C1.431 (2)C6A—H6AA0.970
Cl—O4C1.432 (2)C6A—H6AB0.970
Cl—O1D1.431 (2)C1B—C2B1.368 (5)
Cl—O2D1.432 (2)C1B—H1BA0.930
Cl—O3D1.432 (2)C2B—C3B1.364 (5)
Cl—O4D1.431 (2)C2B—H2BA0.930
N—C6A1.471 (4)C3B—C4B1.371 (5)
N—C6B1.474 (4)C3B—H3BA0.930
N—H1N0.900C4B—C5B1.380 (4)
N—H2N0.900C4B—H4BA0.930
N1A—C5A1.335 (4)C5B—C6B1.502 (4)
N1A—C1A1.340 (4)C6B—H6BA0.970
N1B—C5B1.332 (4)C6B—H6BB0.970
O1A—Cl—O2A109.44 (9)C3A—C2A—H2AA120.9
O1A—Cl—O3A109.34 (9)C2A—C3A—C4A119.1 (4)
O1A—Cl—O4A109.57 (9)C2A—C3A—H3AA120.4
O2A—Cl—O3A109.33 (9)C4A—C3A—H3AA120.4
O2A—Cl—O4A109.58 (9)C5A—C4A—C3A118.5 (4)
O3A—Cl—O4A109.66 (9)C5A—C4A—H4AA120.7
O1B—Cl—O2B109.34 (9)C3A—C4A—H4AA120.7
O1B—Cl—O3B109.33 (9)N1A—C5A—C4A122.6 (3)
O1B—Cl—O4B109.54 (9)N1A—C5A—C6A116.6 (3)
O2B—Cl—O3B109.44 (9)C4A—C5A—C6A120.7 (3)
O2B—Cl—O4B109.63 (9)N—C6A—C5A112.0 (3)
O3B—Cl—O4B109.58 (9)N—C6A—H6AA109.2
O1C—Cl—O2C109.46 (9)C5A—C6A—H6AA109.2
O1C—Cl—O3C109.47 (9)N—C6A—H6AB109.2
O1C—Cl—O4C109.45 (9)C5A—C6A—H6AB109.2
O2C—Cl—O3C109.49 (9)H6AA—C6A—H6AB107.9
O2C—Cl—O4C109.47 (9)N1B—C1B—C2B124.0 (4)
O3C—Cl—O4C109.49 (9)N1B—C1B—H1BA118.0
O1D—Cl—O2D109.48 (9)C2B—C1B—H1BA118.0
O1D—Cl—O3D109.48 (9)C3B—C2B—C1B118.6 (3)
O1D—Cl—O4D109.50 (9)C3B—C2B—H2BA120.7
O2D—Cl—O3D109.44 (9)C1B—C2B—H2BA120.7
O2D—Cl—O4D109.46 (9)C2B—C3B—C4B119.0 (4)
O3D—Cl—O4D109.47 (9)C2B—C3B—H3BA120.5
C6A—N—C6B114.9 (3)C4B—C3B—H3BA120.5
C6A—N—H1N108.5C3B—C4B—C5B118.8 (4)
C6B—N—H1N108.5C3B—C4B—H4BA120.6
C6A—N—H2N108.5C5B—C4B—H4BA120.6
C6B—N—H2N108.5N1B—C5B—C4B123.3 (3)
H1N—N—H2N107.5N1B—C5B—C6B116.4 (3)
C5A—N1A—C1A117.3 (3)C4B—C5B—C6B120.3 (3)
C5B—N1B—C1B116.3 (3)N—C6B—C5B111.7 (3)
N1A—C1A—C2A124.1 (4)N—C6B—H6BA109.3
N1A—C1A—H1AA117.9C5B—C6B—H6BA109.3
C2A—C1A—H1AA117.9N—C6B—H6BB109.3
C1A—C2A—C3A118.3 (4)C5B—C6B—H6BB109.3
C1A—C2A—H2AA120.9H6BA—C6B—H6BB107.9
C5A—N1A—C1A—C2A0.7 (6)C5B—N1B—C1B—C2B0.8 (6)
N1A—C1A—C2A—C3A0.5 (6)N1B—C1B—C2B—C3B0.8 (6)
C1A—C2A—C3A—C4A0.0 (6)C1B—C2B—C3B—C4B0.1 (6)
C2A—C3A—C4A—C5A0.1 (6)C2B—C3B—C4B—C5B0.6 (6)
C1A—N1A—C5A—C4A0.5 (5)C1B—N1B—C5B—C4B0.1 (5)
C1A—N1A—C5A—C6A179.9 (3)C1B—N1B—C5B—C6B179.1 (3)
C3A—C4A—C5A—N1A0.1 (6)C3B—C4B—C5B—N1B0.6 (5)
C3A—C4A—C5A—C6A179.5 (4)C3B—C4B—C5B—C6B178.3 (3)
C6B—N—C6A—C5A178.1 (3)C6A—N—C6B—C5B178.7 (3)
N1A—C5A—C6A—N4.4 (5)N1B—C5B—C6B—N4.3 (5)
C4A—C5A—C6A—N175.0 (3)C4B—C5B—C6B—N176.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H1N···O3Ci0.902.183.015 (17)154
N—H1N···O2Bi0.902.102.789 (10)132
N—H1N···O3Ai0.902.072.869 (7)147
N—H2N···O1C0.902.112.953 (18)155
N—H2N···O1D0.902.102.958 (19)159
N—H2N···O2A0.902.112.875 (9)143
N—H2N···O1B0.902.433.095 (13)130
Symmetry code: (i) x+1/2, y+1/2, z.
 

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