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The cation of the title compound, C12H14N22+·2ClO4, has a centre of symmetry at the mid-point of the central C—C bond. C—H...O hydrogen-bonding inter­actions and π–π inter­actions are present, extending the crystal structure into a three-dimensional supra­molecular network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680701207X/wn2111sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680701207X/wn2111Isup2.hkl
Contains datablock I

CCDC reference: 643133

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.068
  • wR factor = 0.152
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Cl PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.15 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT737_ALERT_1_C D...A Calc 3.172(6), Rep 3.171(2) ...... 3.00 su-Ra C1 -O2 1.555 1.655 PLAT737_ALERT_1_C D...A Calc 3.178(6), Rep 3.178(2) ...... 3.00 su-Ra C2 -O2 1.555 1.655 PLAT737_ALERT_1_C D...A Calc 3.408(6), Rep 3.407(2) ...... 3.00 su-Ra C4 -O3 1.555 3.656 PLAT737_ALERT_1_C D...A Calc 3.243(6), Rep 3.243(2) ...... 3.00 su-Ra C5 -O4 1.555 4.566 PLAT737_ALERT_1_C D...A Calc 3.466(6), Rep 3.469(2) ...... 3.00 su-Ra C6 -O1 1.555 4.566
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 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-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

1,1'-Dimethyl-4,4'-bipyridinium bis(perchlorate) top
Crystal data top
C12H14N22+·2ClO4F(000) = 396
Mr = 385.15Dx = 1.666 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 684 reflections
a = 5.7874 (13) Åθ = 2.7–22.8°
b = 8.8352 (19) ŵ = 0.47 mm1
c = 15.125 (3) ÅT = 293 K
β = 96.972 (3)°Block, colourless
V = 767.7 (3) Å30.26 × 0.14 × 0.10 mm
Z = 2
Data collection top
Bruker APEX CCD area-detector
diffractometer
1500 independent reflections
Radiation source: fine-focus sealed tube961 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
φ and ω scansθmax = 26.1°, θmin = 2.7°
Absorption correction: multi-scan
(SAINT-Plus; Bruker, 2003)
h = 74
Tmin = 0.889, Tmax = 0.956k = 1010
3934 measured reflectionsl = 1818
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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.054P)2 + 0.9834P]
where P = (Fo2 + 2Fc2)/3
1500 reflections(Δ/σ)max < 0.001
110 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.37 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
Cl0.1539 (2)0.11161 (14)0.17742 (7)0.0376 (4)
N10.5413 (7)0.2476 (4)0.4252 (2)0.0352 (10)
O30.2613 (6)0.0171 (4)0.2477 (2)0.0516 (10)
O20.0800 (6)0.1423 (4)0.1921 (2)0.0552 (11)
C40.7646 (9)0.1191 (6)0.5429 (3)0.0408 (12)
H40.79350.09850.60350.049*
C20.8475 (9)0.0876 (5)0.3946 (3)0.0385 (12)
H20.93190.04330.35280.046*
C30.9032 (8)0.0520 (5)0.4839 (3)0.0310 (11)
C60.3468 (10)0.3552 (6)0.3941 (3)0.0541 (15)
H6A0.23280.30410.35320.081*
H6B0.40810.44000.36470.081*
H6C0.27550.39020.44440.081*
C10.6723 (9)0.1858 (6)0.3663 (3)0.0401 (13)
H10.64270.21050.30620.048*
O40.2808 (7)0.2498 (4)0.1765 (2)0.0612 (11)
O10.1566 (7)0.0373 (4)0.0935 (2)0.0611 (12)
C50.5876 (9)0.2143 (5)0.5120 (3)0.0406 (13)
H50.49690.25730.55210.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0441 (7)0.0449 (7)0.0255 (6)0.0038 (7)0.0115 (5)0.0052 (5)
N10.041 (2)0.034 (2)0.031 (2)0.0078 (19)0.0093 (18)0.0051 (17)
O30.058 (2)0.062 (2)0.0354 (19)0.0171 (19)0.0084 (18)0.0199 (17)
O20.046 (2)0.083 (3)0.039 (2)0.016 (2)0.0172 (17)0.0147 (18)
C40.058 (3)0.046 (3)0.021 (2)0.006 (3)0.012 (2)0.005 (2)
C20.047 (3)0.048 (3)0.023 (2)0.008 (3)0.012 (2)0.004 (2)
C30.039 (3)0.030 (3)0.026 (2)0.014 (2)0.011 (2)0.0039 (19)
C60.054 (4)0.065 (4)0.044 (3)0.003 (3)0.005 (3)0.002 (3)
C10.050 (3)0.048 (3)0.024 (2)0.006 (3)0.011 (2)0.001 (2)
O40.080 (3)0.052 (2)0.055 (2)0.024 (2)0.026 (2)0.0015 (19)
O10.076 (3)0.079 (3)0.0307 (19)0.003 (2)0.0165 (19)0.0103 (18)
C50.056 (3)0.040 (3)0.028 (3)0.004 (3)0.013 (2)0.005 (2)
Geometric parameters (Å, º) top
Cl—O21.424 (3)C2—C11.364 (7)
Cl—O41.426 (4)C2—C31.387 (6)
Cl—O11.431 (3)C2—H20.9300
Cl—O31.433 (3)C3—C3i1.485 (9)
N1—C51.341 (6)C6—H6A0.9600
N1—C11.352 (6)C6—H6B0.9600
N1—C61.505 (6)C6—H6C0.9600
C4—C51.363 (7)C1—H10.9300
C4—C31.401 (6)C5—H50.9300
C4—H40.9300
O2—Cl—O4109.8 (2)C2—C3—C4116.2 (4)
O2—Cl—O1109.8 (2)C2—C3—C3i122.4 (5)
O4—Cl—O1108.9 (2)C4—C3—C3i121.4 (5)
O2—Cl—O3109.3 (2)N1—C6—H6A109.5
O4—Cl—O3109.2 (2)N1—C6—H6B109.5
O1—Cl—O3109.9 (2)H6A—C6—H6B109.5
C5—N1—C1119.7 (4)N1—C6—H6C109.5
C5—N1—C6119.8 (4)H6A—C6—H6C109.5
C1—N1—C6120.4 (4)H6B—C6—H6C109.5
C5—C4—C3120.5 (4)N1—C1—C2120.3 (4)
C5—C4—H4119.8N1—C1—H1119.8
C3—C4—H4119.8C2—C1—H1119.8
C1—C2—C3121.7 (4)N1—C5—C4121.5 (4)
C1—C2—H2119.1N1—C5—H5119.2
C3—C2—H2119.1C4—C5—H5119.2
Symmetry code: (i) x+2, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O2ii0.932.573.171 (2)123
C2—H2···O2ii0.932.583.178 (2)123
C4—H4···O3iii0.932.533.407 (2)158
C5—H5···O4iv0.932.383.243 (2)154
C6—H6C···O1iv0.962.533.469 (2)169
Symmetry codes: (ii) x+1, y, z; (iii) x+1, y, z+1; (iv) x, y+1/2, z+1/2.
 

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