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The asymmetric unit of the title compound, (C12H13N2)2[ReO4]I3, contains two 4,4′-dimeth­yl-2,2′-bipyridinium cations, one ReO4 anion and two half-triiodide anions, each anion lying on a centre of symmetry. The crystal packing is stabilized by N—H...O, C—H...O and C—H...I inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805018726/hb6221sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805018726/hb6221Isup2.hkl
Contains datablock I

CCDC reference: 277266

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.026
  • wR factor = 0.059
  • Data-to-parameter ratio = 20.0

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTY02_ALERT_1_C An _exptl_absorpt_correction_type has been given without a literature citation. This should be contained in the _exptl_absorpt_process_details field. Absorption correction given as numerical PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
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 3 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: KM4CCD (Oxford Diffraction, 2004); cell refinement: KM4CCD; data reduction: KM4CCD; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Bis[4,4'-dimethyl-2,2'-bipyridinium(+)] tetraoxorhenium triiodide top
Crystal data top
(C12H13N2)2[ReO4]I3Z = 2
Mr = 1001.40F(000) = 928
Triclinic, P1Dx = 2.276 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.667 (2) ÅCell parameters from 5240 reflections
b = 12.096 (2) Åθ = 3.0–25.0°
c = 14.185 (3) ŵ = 7.36 mm1
α = 66.41 (3)°T = 100 K
β = 85.10 (3)°Block, red
γ = 74.07 (3)°0.30 × 0.15 × 0.10 mm
V = 1461.1 (5) Å3
Data collection top
KM-4/CCD
diffractometer
6808 independent reflections
Radiation source: fine-focus sealed tube5964 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
ω scansθmax = 28.5°, θmin = 3.0°
Absorption correction: numericalh = 1212
Tmin = 0.378, Tmax = 0.595k = 1613
19623 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)] = 0.026Hydrogen site location: difmap (N-H) and geom (C-H)
wR(F2) = 0.059H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0325P)2]
where P = (Fo2 + 2Fc2)/3
6808 reflections(Δ/σ)max = 0.001
340 parametersΔρmax = 1.61 e Å3
0 restraintsΔρmin = 1.09 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
Re10.761289 (15)0.191131 (13)0.612676 (11)0.01351 (5)
O10.6457 (3)0.1071 (3)0.6886 (2)0.0211 (6)
O20.6655 (3)0.3423 (2)0.5396 (2)0.0204 (6)
O30.8860 (3)0.1931 (3)0.6933 (2)0.0196 (6)
O40.8488 (3)0.1189 (3)0.5333 (2)0.0227 (6)
I10.30184 (3)0.97182 (3)0.04451 (2)0.02782 (7)
I20.00001.00000.00000.02189 (8)
I30.79056 (3)0.47696 (3)0.06214 (2)0.03004 (7)
I40.50000.50000.00000.02175 (8)
H1A0.483 (5)0.086 (5)0.655 (4)0.043 (14)*
H2A0.057 (5)0.276 (5)0.644 (4)0.046 (16)*
N10.4706 (3)0.1846 (3)0.4828 (2)0.0148 (6)
N20.4019 (3)0.0476 (3)0.6684 (2)0.0123 (6)
C10.3772 (4)0.0150 (3)0.7679 (3)0.0155 (7)
H10.43670.02030.82030.019*
C20.2657 (4)0.0715 (3)0.7939 (3)0.0151 (7)
H20.25080.11920.86390.018*
C30.1748 (4)0.0580 (3)0.7165 (3)0.0143 (7)
C40.2032 (4)0.0084 (3)0.6135 (3)0.0149 (7)
H40.14280.01790.55990.018*
C50.3193 (4)0.0603 (3)0.5900 (3)0.0114 (7)
C60.3643 (4)0.1313 (3)0.4850 (3)0.0118 (7)
C70.3011 (4)0.1397 (3)0.3971 (3)0.0152 (7)
H70.22790.09880.40290.018*
C80.3462 (4)0.2089 (3)0.2999 (3)0.0151 (7)
C90.4548 (4)0.2649 (3)0.2978 (3)0.0162 (7)
H90.48870.31330.23380.019*
C100.5140 (4)0.2498 (3)0.3898 (3)0.0153 (7)
H100.58920.28780.38630.018*
C110.2805 (4)0.2203 (4)0.2033 (3)0.0202 (8)
H11A0.18070.27140.19490.030*
H11B0.28230.13690.20780.030*
H11C0.33550.26000.14410.030*
C120.0506 (4)0.1167 (4)0.7428 (3)0.0212 (8)
H12A0.00640.10710.67940.032*
H12B0.02090.07550.77980.032*
H12C0.08550.20580.78640.032*
N30.0317 (3)0.3342 (3)0.4812 (2)0.0141 (6)
N40.1246 (3)0.2830 (3)0.6674 (2)0.0125 (6)
C200.1622 (4)0.2446 (3)0.7668 (3)0.0154 (7)
H200.11140.19480.81950.019*
C210.2745 (4)0.2780 (3)0.7917 (3)0.0143 (7)
H210.30080.25210.86180.017*
C220.3497 (4)0.3497 (3)0.7142 (3)0.0124 (7)
C230.3088 (4)0.3854 (3)0.6124 (3)0.0135 (7)
H230.36100.43200.55850.016*
C240.1919 (3)0.3535 (3)0.5882 (3)0.0120 (7)
C250.1361 (4)0.3877 (3)0.4836 (3)0.0125 (7)
C260.1868 (4)0.4692 (3)0.3958 (3)0.0145 (7)
H260.25930.50570.40170.017*
C270.1309 (4)0.4967 (3)0.2994 (3)0.0141 (7)
C280.0233 (4)0.4408 (3)0.2967 (3)0.0171 (8)
H280.01840.45670.23280.021*
C290.0225 (4)0.3619 (3)0.3881 (3)0.0172 (8)
H290.09630.32560.38440.021*
C300.1829 (4)0.5830 (4)0.2024 (3)0.0207 (8)
H30A0.18540.65910.21060.031*
H30B0.11740.60500.14480.031*
H30C0.27980.54120.18840.031*
C310.4720 (4)0.3881 (4)0.7401 (3)0.0197 (8)
H31A0.43890.43080.78710.030*
H31B0.50550.44490.67690.030*
H31C0.55110.31380.77320.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Re10.01382 (7)0.01468 (8)0.01384 (8)0.00674 (5)0.00023 (5)0.00535 (6)
O10.0215 (14)0.0256 (14)0.0159 (14)0.0138 (12)0.0035 (11)0.0021 (12)
O20.0218 (14)0.0155 (13)0.0216 (14)0.0055 (11)0.0035 (11)0.0038 (12)
O30.0173 (13)0.0281 (15)0.0183 (14)0.0127 (11)0.0023 (11)0.0099 (12)
O40.0232 (14)0.0244 (14)0.0262 (15)0.0088 (12)0.0034 (12)0.0146 (13)
I10.03121 (15)0.03595 (16)0.01561 (13)0.01209 (12)0.00124 (11)0.00693 (12)
I20.02687 (19)0.02420 (18)0.01404 (17)0.01041 (15)0.00604 (14)0.00561 (15)
I30.03017 (15)0.03368 (16)0.02406 (14)0.00186 (12)0.00975 (12)0.01133 (13)
I40.02850 (19)0.02214 (18)0.01107 (16)0.00466 (15)0.00027 (14)0.00409 (14)
N10.0141 (15)0.0130 (15)0.0163 (16)0.0043 (12)0.0008 (12)0.0041 (13)
N20.0102 (14)0.0132 (14)0.0140 (15)0.0012 (12)0.0010 (12)0.0069 (13)
C10.0141 (17)0.0189 (18)0.0134 (18)0.0007 (15)0.0016 (14)0.0083 (15)
C20.0138 (17)0.0138 (17)0.0162 (18)0.0038 (14)0.0022 (14)0.0046 (15)
C30.0129 (17)0.0149 (17)0.0175 (18)0.0037 (14)0.0014 (14)0.0091 (15)
C40.0124 (17)0.0166 (18)0.0157 (18)0.0026 (14)0.0000 (14)0.0069 (15)
C50.0092 (16)0.0104 (16)0.0143 (17)0.0001 (13)0.0010 (13)0.0066 (14)
C60.0104 (16)0.0119 (16)0.0125 (17)0.0003 (13)0.0002 (13)0.0062 (14)
C70.0131 (17)0.0119 (17)0.0193 (19)0.0013 (14)0.0003 (15)0.0059 (15)
C80.0167 (18)0.0142 (17)0.0105 (17)0.0013 (14)0.0011 (14)0.0030 (15)
C90.0169 (18)0.0134 (17)0.0133 (18)0.0024 (14)0.0013 (14)0.0014 (15)
C100.0104 (16)0.0172 (18)0.0179 (19)0.0053 (14)0.0008 (14)0.0054 (15)
C110.023 (2)0.021 (2)0.0146 (19)0.0033 (16)0.0026 (16)0.0068 (16)
C120.0207 (19)0.022 (2)0.020 (2)0.0109 (16)0.0027 (16)0.0041 (17)
N30.0095 (14)0.0184 (15)0.0158 (15)0.0018 (12)0.0021 (12)0.0090 (13)
N40.0072 (14)0.0123 (14)0.0171 (16)0.0015 (12)0.0000 (12)0.0054 (13)
C200.0162 (18)0.0124 (17)0.0138 (18)0.0027 (14)0.0015 (14)0.0022 (15)
C210.0144 (17)0.0130 (17)0.0135 (18)0.0003 (14)0.0040 (14)0.0044 (15)
C220.0099 (16)0.0134 (16)0.0153 (17)0.0009 (13)0.0019 (13)0.0082 (15)
C230.0094 (16)0.0130 (17)0.0168 (18)0.0024 (13)0.0002 (14)0.0048 (15)
C240.0084 (16)0.0103 (16)0.0162 (18)0.0008 (13)0.0014 (14)0.0058 (14)
C250.0090 (16)0.0125 (16)0.0172 (18)0.0007 (13)0.0011 (14)0.0089 (15)
C260.0120 (17)0.0130 (17)0.0179 (19)0.0011 (14)0.0000 (14)0.0067 (15)
C270.0126 (17)0.0144 (17)0.0149 (18)0.0014 (14)0.0001 (14)0.0083 (15)
C280.0156 (18)0.0191 (19)0.0186 (19)0.0004 (15)0.0033 (15)0.0114 (16)
C290.0124 (17)0.0215 (19)0.021 (2)0.0046 (15)0.0036 (15)0.0112 (17)
C300.0196 (19)0.027 (2)0.0146 (19)0.0042 (16)0.0003 (15)0.0081 (17)
C310.0169 (19)0.025 (2)0.022 (2)0.0086 (16)0.0018 (16)0.0114 (17)
Geometric parameters (Å, º) top
Re1—O41.723 (3)C11—H11C0.9800
Re1—O11.727 (3)C12—H12A0.9800
Re1—O21.730 (3)C12—H12B0.9800
Re1—O31.741 (3)C12—H12C0.9800
I1—I22.9369 (8)N3—C291.341 (5)
I2—I1i2.9369 (8)N3—C251.349 (4)
I3—I42.9224 (8)N4—C201.344 (5)
I4—I3ii2.9224 (8)N4—C241.350 (4)
N1—C101.339 (5)N4—H2A0.80 (5)
N1—C61.347 (4)C20—C211.373 (5)
N2—C11.345 (5)C20—H200.9500
N2—C51.359 (4)C21—C221.391 (5)
N2—H1A0.99 (5)C21—H210.9500
C1—C21.378 (5)C22—C231.391 (5)
C1—H10.9500C22—C311.504 (5)
C2—C31.396 (5)C23—C241.398 (5)
C2—H20.9500C23—H230.9500
C3—C41.403 (5)C24—C251.480 (5)
C3—C121.504 (5)C25—C261.393 (5)
C4—C51.386 (5)C26—C271.391 (5)
C4—H40.9500C26—H260.9500
C5—C61.488 (5)C27—C281.398 (5)
C6—C71.390 (5)C27—C301.502 (5)
C7—C81.402 (5)C28—C291.389 (5)
C7—H70.9500C28—H280.9500
C8—C91.389 (5)C29—H290.9500
C8—C111.501 (5)C30—H30A0.9800
C9—C101.395 (5)C30—H30B0.9800
C9—H90.9500C30—H30C0.9800
C10—H100.9500C31—H31A0.9800
C11—H11A0.9800C31—H31B0.9800
C11—H11B0.9800C31—H31C0.9800
O4—Re1—O1109.06 (13)H12A—C12—H12B109.5
O4—Re1—O2109.89 (14)C3—C12—H12C109.5
O1—Re1—O2109.96 (13)H12A—C12—H12C109.5
O4—Re1—O3109.79 (12)H12B—C12—H12C109.5
O1—Re1—O3108.12 (12)C29—N3—C25116.6 (3)
O2—Re1—O3110.00 (13)C20—N4—C24123.7 (3)
I1i—I2—I1180.0C20—N4—H2A128 (4)
I3ii—I4—I3180.0C24—N4—H2A108 (4)
C10—N1—C6116.7 (3)N4—C20—C21119.5 (3)
C1—N2—C5122.8 (3)N4—C20—H20120.2
C1—N2—H1A116 (3)C21—C20—H20120.2
C5—N2—H1A121 (3)C20—C21—C22120.0 (3)
N2—C1—C2120.1 (3)C20—C21—H21120.0
N2—C1—H1120.0C22—C21—H21120.0
C2—C1—H1120.0C23—C22—C21118.5 (3)
C1—C2—C3119.4 (3)C23—C22—C31120.8 (3)
C1—C2—H2120.3C21—C22—C31120.7 (3)
C3—C2—H2120.3C22—C23—C24120.8 (3)
C2—C3—C4119.0 (3)C22—C23—H23119.6
C2—C3—C12120.5 (3)C24—C23—H23119.6
C4—C3—C12120.5 (3)N4—C24—C23117.3 (3)
C5—C4—C3120.1 (3)N4—C24—C25116.6 (3)
C5—C4—H4120.0C23—C24—C25126.1 (3)
C3—C4—H4120.0N3—C25—C26123.4 (3)
N2—C5—C4118.6 (3)N3—C25—C24114.1 (3)
N2—C5—C6115.1 (3)C26—C25—C24122.4 (3)
C4—C5—C6126.3 (3)C27—C26—C25119.7 (3)
N1—C6—C7123.5 (3)C27—C26—H26120.2
N1—C6—C5114.8 (3)C25—C26—H26120.2
C7—C6—C5121.7 (3)C26—C27—C28117.0 (3)
C6—C7—C8119.6 (3)C26—C27—C30121.7 (3)
C6—C7—H7120.2C28—C27—C30121.3 (3)
C8—C7—H7120.2C29—C28—C27119.7 (3)
C9—C8—C7116.9 (3)C29—C28—H28120.2
C9—C8—C11122.0 (3)C27—C28—H28120.2
C7—C8—C11121.2 (3)N3—C29—C28123.7 (3)
C8—C9—C10119.8 (3)N3—C29—H29118.2
C8—C9—H9120.1C28—C29—H29118.2
C10—C9—H9120.1C27—C30—H30A109.5
N1—C10—C9123.6 (3)C27—C30—H30B109.5
N1—C10—H10118.2H30A—C30—H30B109.5
C9—C10—H10118.2C27—C30—H30C109.5
C8—C11—H11A109.5H30A—C30—H30C109.5
C8—C11—H11B109.5H30B—C30—H30C109.5
H11A—C11—H11B109.5C22—C31—H31A109.5
C8—C11—H11C109.5C22—C31—H31B109.5
H11A—C11—H11C109.5H31A—C31—H31B109.5
H11B—C11—H11C109.5C22—C31—H31C109.5
C3—C12—H12A109.5H31A—C31—H31C109.5
C3—C12—H12B109.5H31B—C31—H31C109.5
C5—N2—C1—C21.1 (5)C24—N4—C20—C210.4 (5)
N2—C1—C2—C33.0 (5)N4—C20—C21—C220.8 (5)
C1—C2—C3—C42.7 (5)C20—C21—C22—C230.3 (5)
C1—C2—C3—C12178.9 (3)C20—C21—C22—C31179.3 (3)
C2—C3—C4—C50.5 (5)C21—C22—C23—C242.0 (5)
C12—C3—C4—C5178.9 (3)C31—C22—C23—C24177.7 (3)
C1—N2—C5—C41.2 (5)C20—N4—C24—C231.3 (5)
C1—N2—C5—C6179.2 (3)C20—N4—C24—C25179.8 (3)
C3—C4—C5—N21.4 (5)C22—C23—C24—N42.5 (5)
C3—C4—C5—C6179.0 (3)C22—C23—C24—C25178.7 (3)
C10—N1—C6—C70.8 (5)C29—N3—C25—C260.7 (5)
C10—N1—C6—C5179.8 (3)C29—N3—C25—C24179.8 (3)
N2—C5—C6—N17.0 (4)N4—C24—C25—N35.4 (4)
C4—C5—C6—N1172.6 (3)C23—C24—C25—N3173.4 (3)
N2—C5—C6—C7172.4 (3)N4—C24—C25—C26174.1 (3)
C4—C5—C6—C78.0 (5)C23—C24—C25—C267.1 (5)
N1—C6—C7—C81.4 (5)N3—C25—C26—C271.3 (5)
C5—C6—C7—C8179.3 (3)C24—C25—C26—C27179.3 (3)
C6—C7—C8—C90.7 (5)C25—C26—C27—C280.9 (5)
C6—C7—C8—C11179.9 (3)C25—C26—C27—C30179.5 (3)
C7—C8—C9—C100.4 (5)C26—C27—C28—C290.1 (5)
C11—C8—C9—C10179.0 (3)C30—C27—C28—C29179.7 (3)
C6—N1—C10—C90.4 (5)C25—N3—C29—C280.2 (5)
C8—C9—C10—N11.0 (5)C27—C28—C29—N30.5 (5)
Symmetry codes: (i) x, y+2, z; (ii) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1A···O10.99 (5)1.79 (5)2.714 (4)154 (5)
N4—H2A···O3iii0.80 (5)2.09 (5)2.748 (4)140 (5)
C4—H4···O4iv0.952.483.183 (5)130
C23—H23···O2v0.952.463.199 (5)133
C26—H26···O2v0.952.583.429 (5)148
C30—H30A···O3v0.982.573.466 (6)151
C20—H20···I2vi0.953.053.998 (4)169
Symmetry codes: (iii) x1, y, z; (iv) x+1, y, z+1; (v) x+1, y+1, z+1; (vi) x, y1, z+1.
 

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