Download citation
Download citation
link to html
In the title compound, [Cu(C12H12N2)2]ClO4, the CuI atom is chelated by two heterocyclic ligands in a tetrahedral coordination geometry. The compound exists as cations and anions with only Coulombic interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804031939/ob6449sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031939/ob6449Isup2.hkl
Contains datablock I

CCDC reference: 262243

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • Disorder in solvent or counterion
  • R factor = 0.049
  • wR factor = 0.151
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for O1' PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for O2 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for O3 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for O3' PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for O4 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for O4' PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for O2' PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 44.00 Perc. PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C1 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C12 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C24
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 12 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: atomic coordinates taken from the tetrafluoroborate structure; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Bis(6,6'-dimethyl-2,2'-bipyridine)copper(I) perchlorate top
Crystal data top
[Cu(C12H12N2)2]ClO4F(000) = 1096
Mr = 531.46Dx = 1.460 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 844 reflections
a = 12.355 (1) Åθ = 1.7–26.3°
b = 21.912 (2) ŵ = 1.05 mm1
c = 8.972 (1) ÅT = 293 K
β = 95.58 (1)°Bar, red
V = 2417.3 (4) Å30.20 × 0.18 × 0.18 mm
Z = 4
Data collection top
Bruker SMART area-detector
diffractometer
4892 independent reflections
Radiation source: medium-focus sealed tube3155 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
φ and ω scanθmax = 26.3°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1515
Tmin = 0.817, Tmax = 0.833k = 2726
13742 measured reflectionsl = 611
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0781P)2 + 1.2121P]
where P = (Fo2 + 2Fc2)/3
4892 reflections(Δ/σ)max = 0.001
343 parametersΔρmax = 0.47 e Å3
142 restraintsΔρmin = 0.39 e Å3
Special details top

Refinement. The large number of restraints, 142, comes from the use of the SADI command, which allows more 'breathing'. (The use of a DFIX command would lower the number of restraints).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cu10.29212 (4)0.62527 (2)0.41155 (6)0.0465 (2)
Cl10.79690 (9)0.62702 (6)0.0791 (2)0.0652 (3)
O10.8969 (5)0.5970 (4)0.073 (1)0.091 (3)0.50
O20.788 (1)0.6688 (5)0.195 (1)0.156 (7)0.50
O30.7129 (7)0.5856 (5)0.086 (2)0.150 (5)0.50
O40.7966 (9)0.6602 (5)0.0580 (9)0.128 (4)0.50
O1'0.8614 (9)0.5843 (4)0.143 (1)0.143 (5)0.50
O2'0.8134 (8)0.6839 (3)0.151 (1)0.079 (3)0.50
O3'0.6880 (6)0.6122 (5)0.108 (2)0.139 (5)0.50
O4'0.827 (1)0.6340 (5)0.0720 (8)0.158 (6)0.50
N10.3212 (3)0.6048 (2)0.1956 (3)0.0434 (8)
N20.4505 (2)0.6515 (1)0.4228 (4)0.0409 (7)
N30.1669 (2)0.6742 (1)0.4809 (3)0.0401 (7)
N40.2178 (2)0.5575 (1)0.5227 (4)0.0412 (7)
C10.1391 (4)0.5669 (3)0.1264 (6)0.076 (2)
C20.2548 (4)0.5750 (2)0.0943 (5)0.057 (1)
C30.2925 (5)0.5521 (3)0.0341 (6)0.078 (2)
C40.3985 (6)0.5600 (3)0.0587 (6)0.087 (2)
C50.4668 (4)0.5903 (2)0.0450 (5)0.068 (1)
C60.4262 (3)0.6126 (2)0.1708 (4)0.045 (1)
C70.4950 (3)0.6445 (2)0.2912 (5)0.043 (1)
C80.5984 (3)0.6652 (2)0.2725 (6)0.055 (1)
C90.6576 (3)0.6936 (2)0.3900 (7)0.064 (1)
C100.6148 (4)0.6997 (2)0.5239 (6)0.063 (1)
C110.5089 (3)0.6784 (2)0.5377 (5)0.049 (1)
C120.4572 (4)0.6852 (3)0.6794 (5)0.077 (2)
C130.3495 (4)0.4808 (2)0.4694 (7)0.082 (2)
C140.2489 (3)0.4993 (2)0.5389 (5)0.050 (1)
C150.1902 (4)0.4577 (2)0.6160 (5)0.059 (1)
C160.1006 (4)0.4772 (2)0.6790 (5)0.060 (1)
C170.0673 (3)0.5365 (2)0.6611 (5)0.051 (1)
C180.1268 (3)0.5762 (2)0.5813 (4)0.040 (1)
C190.0973 (3)0.6409 (2)0.5546 (4)0.041 (1)
C200.0039 (3)0.6665 (2)0.6020 (5)0.058 (1)
C210.0187 (4)0.7264 (2)0.5732 (6)0.069 (1)
C220.0525 (4)0.7605 (2)0.5001 (5)0.063 (1)
C230.1453 (3)0.7333 (2)0.4552 (5)0.050 (1)
C240.2278 (4)0.7684 (2)0.3768 (6)0.068 (1)
H1a0.12840.58580.22040.114*
H1b0.12280.52410.13130.114*
H1c0.09180.58550.04810.114*
H30.24550.53140.10390.093*
H40.42420.54480.14540.104*
H50.53970.59570.03040.082*
H80.62740.66000.18150.066*
H90.72670.70860.37850.077*
H100.65520.71780.60500.076*
H12a0.38540.66810.66730.115*
H12b0.45270.72770.70400.115*
H12c0.50000.66430.75860.115*
H13a0.37800.51540.42050.123*
H13b0.33200.44910.39740.123*
H13c0.40290.46620.54590.123*
H150.21200.41710.62440.071*
H160.06200.45030.73410.072*
H170.00530.54990.70210.062*
H200.04300.64300.65320.069*
H210.08170.74390.60290.083*
H220.03860.80160.48070.075*
H24a0.28580.74170.35530.102*
H24b0.25670.80110.44020.102*
H24c0.19360.78510.28500.102*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0376 (3)0.0497 (3)0.0552 (3)0.0029 (2)0.0205 (2)0.0009 (2)
Cl10.0495 (6)0.0663 (7)0.0846 (9)0.0002 (6)0.0301 (6)0.0040 (7)
O10.062 (4)0.092 (6)0.120 (7)0.031 (4)0.014 (5)0.006 (5)
O20.133 (9)0.18 (1)0.15 (1)0.008 (8)0.018 (7)0.032 (8)
O30.099 (7)0.124 (8)0.24 (1)0.035 (6)0.048 (7)0.032 (7)
O40.134 (7)0.129 (8)0.133 (8)0.011 (6)0.077 (6)0.035 (6)
O1'0.142 (9)0.121 (8)0.18 (1)0.018 (7)0.087 (7)0.017 (7)
O2'0.084 (5)0.058 (4)0.094 (5)0.004 (4)0.002 (5)0.001 (4)
O3'0.073 (6)0.163 (9)0.186 (9)0.028 (6)0.040 (6)0.009 (7)
O4'0.19 (1)0.16 (1)0.120 (8)0.025 (8)0.015 (7)0.050 (7)
N10.044 (2)0.043 (2)0.044 (2)0.001 (1)0.007 (2)0.005 (1)
N20.033 (2)0.040 (2)0.051 (2)0.001 (1)0.010 (1)0.0027 (15)
N30.037 (2)0.045 (2)0.040 (2)0.002 (1)0.009 (1)0.000 (1)
N40.033 (2)0.041 (2)0.051 (2)0.003 (1)0.010 (1)0.002 (2)
C10.058 (3)0.081 (4)0.085 (4)0.016 (3)0.009 (3)0.008 (3)
C20.064 (3)0.053 (3)0.053 (3)0.000 (2)0.000 (2)0.000 (2)
C30.098 (4)0.080 (4)0.052 (3)0.005 (3)0.005 (3)0.018 (3)
C40.109 (5)0.100 (5)0.054 (3)0.006 (4)0.024 (3)0.018 (3)
C50.066 (3)0.083 (4)0.060 (3)0.010 (3)0.029 (2)0.003 (3)
C60.048 (2)0.045 (2)0.044 (2)0.006 (2)0.013 (2)0.008 (2)
C70.039 (2)0.038 (2)0.053 (2)0.006 (2)0.015 (2)0.008 (2)
C80.040 (2)0.051 (3)0.077 (3)0.004 (2)0.025 (2)0.015 (2)
C90.037 (2)0.049 (3)0.109 (4)0.006 (2)0.021 (3)0.008 (3)
C100.045 (2)0.048 (3)0.095 (4)0.007 (2)0.004 (2)0.007 (2)
C110.048 (2)0.043 (2)0.057 (3)0.000 (2)0.007 (2)0.003 (2)
C120.080 (4)0.092 (4)0.060 (3)0.018 (3)0.013 (3)0.018 (3)
C130.065 (3)0.061 (3)0.126 (5)0.021 (3)0.039 (3)0.018 (3)
C140.038 (2)0.048 (2)0.062 (3)0.003 (2)0.006 (2)0.004 (2)
C150.055 (3)0.043 (2)0.079 (3)0.006 (2)0.004 (2)0.012 (2)
C160.049 (2)0.058 (3)0.075 (3)0.013 (2)0.011 (2)0.020 (2)
C170.036 (2)0.063 (3)0.057 (3)0.008 (2)0.013 (2)0.005 (2)
C180.031 (2)0.050 (2)0.038 (2)0.005 (2)0.003 (2)0.001 (2)
C190.033 (2)0.049 (2)0.041 (2)0.000 (2)0.009 (2)0.000 (2)
C200.046 (2)0.064 (3)0.067 (3)0.008 (2)0.022 (2)0.004 (2)
C210.053 (3)0.074 (3)0.086 (4)0.020 (2)0.027 (3)0.001 (3)
C220.064 (3)0.048 (3)0.077 (3)0.018 (2)0.013 (3)0.005 (2)
C230.052 (2)0.047 (2)0.051 (2)0.004 (2)0.008 (2)0.004 (2)
C240.074 (3)0.051 (3)0.081 (3)0.002 (2)0.020 (3)0.017 (2)
Geometric parameters (Å, º) top
Cu1—N12.054 (3)C15—C161.361 (6)
Cu1—N22.033 (3)C16—C171.366 (6)
Cu1—N32.029 (3)C17—C181.383 (5)
Cu1—N42.055 (3)C18—C191.479 (5)
Cl1—O11.396 (5)C19—C201.386 (5)
Cl1—O21.378 (7)C20—C211.360 (6)
Cl1—O31.375 (6)C21—C221.368 (6)
Cl1—O41.429 (6)C22—C231.387 (6)
Cl1—O1'1.386 (6)C23—C241.505 (6)
Cl1—O2'1.429 (6)C1—H1a0.96
Cl1—O3'1.385 (6)C1—H1b0.96
Cl1—O4'1.379 (7)C1—H1c0.96
N1—C21.334 (5)C3—H30.93
N1—C61.349 (5)C4—H40.93
N2—C111.336 (5)C5—H50.93
N2—C71.359 (5)C8—H80.93
N3—C231.339 (5)C9—H90.93
N3—C191.348 (5)C10—H100.93
N4—C141.336 (5)C12—H12a0.96
N4—C181.349 (5)C12—H12b0.96
C1—C21.496 (7)C12—H12c0.96
C2—C31.379 (7)C13—H13a0.96
C3—C41.359 (8)C13—H13b0.96
C4—C51.367 (8)C13—H13c0.96
C5—C61.370 (6)C15—H150.93
C6—C71.483 (6)C16—H160.93
C7—C81.381 (5)C17—H170.93
C8—C91.373 (7)C20—H200.93
C9—C101.365 (7)C21—H210.93
C10—C111.406 (6)C22—H220.93
C11—C121.485 (6)C24—H24a0.96
C13—C141.499 (6)C24—H24b0.96
C14—C151.390 (6)C24—H24c0.96
N1—Cu1—N281.6 (1)N3—C19—C20121.4 (4)
N1—Cu1—N3127.8 (1)N3—C19—C18116.0 (3)
N1—Cu1—N4115.3 (1)C20—C19—C18122.6 (3)
N2—Cu1—N3126.5 (1)C21—C20—C19119.6 (4)
N2—Cu1—N4130.9 (1)C20—C21—C22119.2 (4)
N3—Cu1—N480.9 (1)C21—C22—C23119.6 (4)
O3—Cl1—O2113.7 (5)N3—C23—C22121.4 (4)
O4'—Cl1—O3'112.1 (5)N3—C23—C24116.3 (4)
O4'—Cl1—O1'111.5 (5)C22—C23—C24122.2 (4)
O3'—Cl1—O1'110.5 (5)C2—C1—H1a109.5
O3—Cl1—O1110.6 (5)C2—C1—H1b109.5
O2—Cl1—O1110.3 (5)H1a—C1—H1b109.5
O4'—Cl1—O2'108.2 (5)C2—C1—H1c109.5
O3'—Cl1—O2'107.3 (5)H1a—C1—H1c109.5
O1'—Cl1—O2'106.8 (5)H1b—C1—H1c109.5
O3—Cl1—O4108.0 (5)C4—C3—H3120.0
O2—Cl1—O4107.6 (5)C2—C3—H3120.0
O1—Cl1—O4106.4 (5)C3—C4—H4120.3
C2—N1—C6119.2 (4)C5—C4—H4120.3
C2—N1—Cu1126.7 (3)C4—C5—H5120.6
C6—N1—Cu1112.8 (3)C6—C5—H5120.6
C11—N2—C7119.1 (3)C9—C8—H8120.5
C11—N2—Cu1127.5 (3)C7—C8—H8120.5
C7—N2—Cu1113.2 (3)C10—C9—H9120.1
C23—N3—C19118.8 (3)C8—C9—H9120.1
C23—N3—Cu1127.1 (3)C9—C10—H10120.4
C19—N3—Cu1114.0 (2)C11—C10—H10120.4
C14—N4—C18119.3 (3)C11—C12—H12a109.5
C14—N4—Cu1127.2 (3)C11—C12—H12b109.5
C18—N4—Cu1113.5 (2)H12a—C12—H12b109.5
N1—C2—C3120.8 (4)C11—C12—H12c109.5
N1—C2—C1117.6 (4)H12a—C12—H12c109.5
C3—C2—C1121.7 (5)H12b—C12—H12c109.5
C4—C3—C2119.9 (5)C14—C13—H13a109.5
C3—C4—C5119.5 (5)C14—C13—H13b109.5
C4—C5—C6118.9 (5)H13a—C13—H13b109.5
N1—C6—C5121.8 (4)C14—C13—H13c109.5
N1—C6—C7115.6 (3)H13a—C13—H13c109.5
C5—C6—C7122.6 (4)H13b—C13—H13c109.5
N2—C7—C8121.7 (4)C16—C15—H15120.5
N2—C7—C6115.8 (3)C14—C15—H15120.5
C8—C7—C6122.5 (4)C15—C16—H16120.1
C9—C8—C7119.1 (4)C17—C16—H16120.1
C10—C9—C8119.8 (4)C16—C17—H17120.4
C9—C10—C11119.3 (4)C18—C17—H17120.4
N2—C11—C10121.1 (4)C21—C20—H20120.2
N2—C11—C12117.3 (4)C19—C20—H20120.2
C10—C11—C12121.6 (4)C20—C21—H21120.4
N4—C14—C15121.4 (4)C22—C21—H21120.4
N4—C14—C13117.0 (4)C21—C22—H22120.2
C15—C14—C13121.6 (4)C23—C22—H22120.2
C16—C15—C14119.1 (4)C23—C24—H24a109.5
C15—C16—C17119.9 (4)C23—C24—H24b109.5
C16—C17—C18119.3 (4)H24a—C24—H24b109.5
N4—C18—C17121.0 (4)C23—C24—H24c109.5
N4—C18—C19115.5 (3)H24a—C24—H24c109.5
C17—C18—C19123.5 (3)H24b—C24—H24c109.5
N3—Cu1—N1—C257.9 (4)N1—C6—C7—C8168.7 (4)
N2—Cu1—N1—C2171.8 (4)C5—C6—C7—C813.8 (6)
N4—Cu1—N1—C240.5 (4)N2—C7—C8—C90.1 (6)
N3—Cu1—N1—C6135.6 (3)C6—C7—C8—C9179.1 (4)
N2—Cu1—N1—C65.4 (3)C7—C8—C9—C101.4 (7)
N4—Cu1—N1—C6126.0 (3)C8—C9—C10—C111.9 (7)
N3—Cu1—N2—C1143.9 (4)C7—N2—C11—C100.5 (6)
N1—Cu1—N2—C11175.3 (3)Cu1—N2—C11—C10173.4 (3)
N4—Cu1—N2—C1168.4 (4)C7—N2—C11—C12180.0 (4)
N3—Cu1—N2—C7130.3 (2)Cu1—N2—C11—C126.1 (6)
N1—Cu1—N2—C71.1 (3)C9—C10—C11—N21.0 (7)
N4—Cu1—N2—C7117.4 (3)C9—C10—C11—C12178.5 (4)
N2—Cu1—N3—C2345.5 (4)C18—N4—C14—C150.7 (6)
N1—Cu1—N3—C2364.6 (4)Cu1—N4—C14—C15179.3 (3)
N4—Cu1—N3—C23179.6 (3)C18—N4—C14—C13179.0 (4)
N2—Cu1—N3—C19137.7 (3)Cu1—N4—C14—C130.4 (6)
N1—Cu1—N3—C19112.2 (3)N4—C14—C15—C161.4 (7)
N4—Cu1—N3—C192.8 (3)C13—C14—C15—C16178.9 (5)
N3—Cu1—N4—C14180.0 (4)C14—C15—C16—C172.4 (7)
N2—Cu1—N4—C1448.8 (4)C15—C16—C17—C181.3 (7)
N1—Cu1—N4—C1452.3 (4)C14—N4—C18—C171.8 (6)
N3—Cu1—N4—C181.3 (3)Cu1—N4—C18—C17179.3 (3)
N2—Cu1—N4—C18132.4 (3)C14—N4—C18—C19178.5 (3)
N1—Cu1—N4—C18126.4 (3)Cu1—N4—C18—C190.3 (4)
C6—N1—C2—C30.3 (6)C16—C17—C18—N40.9 (6)
Cu1—N1—C2—C3165.3 (4)C16—C17—C18—C19179.5 (4)
C6—N1—C2—C1179.6 (4)C23—N3—C19—C200.8 (6)
Cu1—N1—C2—C114.0 (6)Cu1—N3—C19—C20176.3 (3)
N1—C2—C3—C40.2 (8)C23—N3—C19—C18179.1 (3)
C1—C2—C3—C4179.4 (5)Cu1—N3—C19—C183.8 (4)
C2—C3—C4—C50.3 (9)N4—C18—C19—N32.8 (5)
C3—C4—C5—C60.7 (9)C17—C18—C19—N3176.9 (4)
C2—N1—C6—C50.7 (6)N4—C18—C19—C20177.3 (4)
Cu1—N1—C6—C5166.8 (3)C17—C18—C19—C203.0 (6)
C2—N1—C6—C7178.2 (3)N3—C19—C20—C210.4 (7)
Cu1—N1—C6—C710.7 (4)C18—C19—C20—C21179.7 (4)
C4—C5—C6—N10.9 (7)C19—C20—C21—C221.2 (7)
C4—C5—C6—C7178.2 (5)C20—C21—C22—C230.8 (8)
C11—N2—C7—C81.0 (6)C19—N3—C23—C221.2 (6)
Cu1—N2—C7—C8173.7 (3)Cu1—N3—C23—C22175.4 (3)
C11—N2—C7—C6178.2 (3)C19—N3—C23—C24178.1 (4)
Cu1—N2—C7—C67.1 (4)Cu1—N3—C23—C245.2 (5)
N1—C6—C7—N212.1 (5)C21—C22—C23—N30.4 (7)
C5—C6—C7—N2165.4 (4)C21—C22—C23—C24178.9 (5)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds