Download citation
Download citation
link to html
In the title complex, [Cu(CH3O)2(C40H40N8)](ClO4)2, two copper ions are bridged by two methoxide O atoms. Each CuII is further coordinated by two neutral 3-methyl-5-phenyl-1H-pyrazole ligands and adopts a distorted square-planar geometry. The two perchlorate anions lie on opposite sides of the Cu2O2 plane and there is evidence for inter­action between two of the O atoms from each perchlorate anion with the CuII centers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042079/sj2335sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042079/sj2335Isup2.hkl
Contains datablock I

CCDC reference: 663544

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.049
  • wR factor = 0.137
  • Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 8.11 Ratio
Author Response: poor data, not adequate for the refinement of individual displacement parameters

Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.91 Ratio PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C12 PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C24 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C36
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 3.12 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for Cl1 - O4 .. 5.50 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O4 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O9 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C31 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C34 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C38 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C5 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C26 PLAT245_ALERT_2_C U(iso) H44 Smaller than U(eq) N6 by ... 0.02 AngSq PLAT245_ALERT_2_C U(iso) H45 Smaller than U(eq) N8 by ... 0.02 AngSq PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C11 -C16 1.36 Ang. PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C31 -C36 1.37 Ang. PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 9 PLAT352_ALERT_3_C Short N-H Bond (0.87A) N5 - H46 ... 0.75 Ang. PLAT352_ALERT_3_C Short N-H Bond (0.87A) N8 - H45 ... 0.70 Ang. PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 79.00 A   3
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 PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1 (2) 2.13 PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu2 (2) 2.11
1 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 20 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 20 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL022_ALERT_1_A There is a mismatched ~ on line 243 _chemical_formula_iupac '[Cu (C H3 O)2 (C40 H40 N8)] (Cl O4)~2' If you require a ~ then it should be escaped with a \, i.e. \~ Otherwise there must be a matching closing ~, e.g. C~2~H~4~
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Comment top

3-methyl-5-phenyl-1H-pyrazole has been widely used as starting material for the preparation of the trispyrazolylborate anion, and as a very good ligand for modeling complexes of several metalloenzymes (Tekeste & Vahrenkamp 2007; Jacobsen & Cohen, 2004; Puerta & Cohen, 2003; Parkin, 2004). However, its interaction with transition metal ions is rare. Reported here is the single-crystal structure of a dicopper(II) complex of this ligand.

In the title compound (I) two methoxide anions hold two copper ions together with O as the bridging atoms. The distance between Cu1 and Cu2 is 2.9583 (7) Å. Each copper ion is further coordinated by two pyrazolyl N atoms. Copper adopts an approximate square planar geometry. Atoms N1, N2, N3, N4, Cu1, and Cu2 are almost coplanar with a torsion angle of 3.4 (3)° between the N1/N2/Cu2 and N3/N4/Cu1 planes. The two bridging methoxyl groups are located on either side of this plane. The torsion angles between the O1/Cu1/Cu2 and O2/Cu1/Cu2 planes and that containing the atoms N1/N2/N3/N4/Cu1/Cu2 are 12.30 (16)° and -12.30 (16)°, respectively. The Cu1/O1/Cu2/O2 ring is also planar with an r.m.s. deviation from the best fit meanplane of 0.0002. The O4, O9 and O3, O8 atoms from the two perchlorate anions point towards the Cu1 and Cu2 centers with distances 2.722 (3), 2.755 (3), 2.790 (3), and 2.869 (3) Å for O3—Cu2, O4—Cu1, O8—Cu2, and O9—Cu1, respectively. This indicates some level of interaction between the perchlorate anions and the CuII cations.

Related literature top

For related literature, see: Jacobsen & Cohen (2004); Parkin (2004); Puerta & Cohen (2003); Tekeste & Vahrenkamp (2007).

Experimental top

3-methyl-5-phenyl-1H-pyrazole (0.16 g, 0.1 mmol), prepared according to the literature (Puerta & Cohen, 2003), was dissolved in dichloromethane (10 ml) at room temperature. To this solution, copper(II) perchlorate hexahydrate (0.18 g, 0.05 mmol) in methanol (2 ml) was added. The resulting blue solution was stirred for two hours. The mixture was filtered and the filtrate kept at room temperature. Blue crystals were obtained after one week by slow evaporation.

Refinement top

H atoms on N5, N6, N7, and N8 are refined while the other hydrogen atoms are geometrically constrained and refined in riding mode as follows: methyl C—H = 0.96 Å, Uiso(H) = 1.5Ueq(C); aromatic C—H = 0.93 Å, Uiso(H) = 1.2Ueq(C). High and increasing temperature factors for the C atoms of the C1···C6 and C31···C36 benzene rings suggested possible disorder but this was not investigated further.

Structure description top

3-methyl-5-phenyl-1H-pyrazole has been widely used as starting material for the preparation of the trispyrazolylborate anion, and as a very good ligand for modeling complexes of several metalloenzymes (Tekeste & Vahrenkamp 2007; Jacobsen & Cohen, 2004; Puerta & Cohen, 2003; Parkin, 2004). However, its interaction with transition metal ions is rare. Reported here is the single-crystal structure of a dicopper(II) complex of this ligand.

In the title compound (I) two methoxide anions hold two copper ions together with O as the bridging atoms. The distance between Cu1 and Cu2 is 2.9583 (7) Å. Each copper ion is further coordinated by two pyrazolyl N atoms. Copper adopts an approximate square planar geometry. Atoms N1, N2, N3, N4, Cu1, and Cu2 are almost coplanar with a torsion angle of 3.4 (3)° between the N1/N2/Cu2 and N3/N4/Cu1 planes. The two bridging methoxyl groups are located on either side of this plane. The torsion angles between the O1/Cu1/Cu2 and O2/Cu1/Cu2 planes and that containing the atoms N1/N2/N3/N4/Cu1/Cu2 are 12.30 (16)° and -12.30 (16)°, respectively. The Cu1/O1/Cu2/O2 ring is also planar with an r.m.s. deviation from the best fit meanplane of 0.0002. The O4, O9 and O3, O8 atoms from the two perchlorate anions point towards the Cu1 and Cu2 centers with distances 2.722 (3), 2.755 (3), 2.790 (3), and 2.869 (3) Å for O3—Cu2, O4—Cu1, O8—Cu2, and O9—Cu1, respectively. This indicates some level of interaction between the perchlorate anions and the CuII cations.

For related literature, see: Jacobsen & Cohen (2004); Parkin (2004); Puerta & Cohen (2003); Tekeste & Vahrenkamp (2007).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b) and publCIF (Version 1.0_c; Westrip, 2007).

Figures top
[Figure 1] Fig. 1. The structure of (I) with displacement ellipsoids drawn at the 30% probability level. Hydrogen atoms are drawn as small circles of arbitrary radii.
Di-µ-methoxido-κ4O:O-bis[bis(3-methyl-5-phenyl-1H-pyrazole- κN2)copper(II)] bis(perchlorate) top
Crystal data top
[Cu(CH3O)2(C40H40N8)](ClO4)2F(000) = 2104
Mr = 1020.85Dx = 1.392 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9998 reflections
a = 13.8398 (12) Åθ = 1.0–25.5°
b = 17.4607 (16) ŵ = 1.04 mm1
c = 20.3779 (18) ÅT = 293 K
β = 98.316 (1)°Block, green
V = 4872.6 (8) Å30.15 × 0.13 × 0.11 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer
9045 independent reflections
Radiation source: fine-focus sealed tube5370 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.074
φ and ω scansθmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
h = 1616
Tmin = 0.859, Tmax = 0.894k = 2121
48197 measured reflectionsl = 2424
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) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0637P)2 + 2.32P]
where P = (Fo2 + 2Fc2)/3
9045 reflections(Δ/σ)max = 0.003
599 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
[Cu(CH3O)2(C40H40N8)](ClO4)2V = 4872.6 (8) Å3
Mr = 1020.85Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.8398 (12) ŵ = 1.04 mm1
b = 17.4607 (16) ÅT = 293 K
c = 20.3779 (18) Å0.15 × 0.13 × 0.11 mm
β = 98.316 (1)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
9045 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
5370 reflections with I > 2σ(I)
Tmin = 0.859, Tmax = 0.894Rint = 0.074
48197 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.46 e Å3
9045 reflectionsΔρmin = 0.26 e Å3
599 parameters
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
C11.3406 (6)0.4300 (5)0.5628 (4)0.145 (4)
H11.33180.46110.59850.175*
C21.4292 (6)0.4221 (6)0.5433 (6)0.150 (4)
H21.48130.44900.56640.180*
C31.4469 (5)0.3770 (5)0.4917 (6)0.129 (4)
H31.50930.37260.48020.155*
C41.3675 (4)0.3376 (4)0.4566 (4)0.115 (3)
H41.37660.30790.42010.138*
C51.2766 (4)0.3425 (3)0.4754 (3)0.0762 (17)
C61.2628 (5)0.3900 (5)0.5277 (4)0.116 (3)
H61.20070.39520.53950.139*
C71.1920 (3)0.3031 (3)0.4369 (3)0.0603 (13)
C81.1693 (4)0.2811 (3)0.3721 (3)0.0744 (16)
H81.20950.28580.33950.089*
C91.0756 (4)0.2504 (3)0.3632 (2)0.0599 (13)
C101.0161 (5)0.2209 (4)0.3027 (2)0.100 (2)
H10A1.02880.16720.29820.150*
H10B1.03270.24780.26480.150*
H10C0.94820.22840.30560.150*
C110.6050 (4)0.0721 (4)0.3064 (3)0.104 (2)
H110.61000.11990.32670.125*
C120.5160 (4)0.0492 (4)0.2717 (4)0.138 (3)
H120.46250.08190.26800.165*
C130.5072 (5)0.0208 (4)0.2432 (4)0.109 (2)
H130.44720.03720.22120.130*
C140.5860 (5)0.0666 (4)0.2469 (3)0.0900 (19)
H140.58080.11430.22640.108*
C150.6742 (4)0.0434 (3)0.2809 (3)0.0735 (16)
H150.72780.07600.28330.088*
C160.6847 (3)0.0265 (3)0.3113 (2)0.0541 (12)
C170.7801 (3)0.0507 (2)0.3463 (2)0.0447 (10)
C180.8683 (3)0.0142 (2)0.3584 (2)0.0546 (12)
H180.88180.03530.34550.065*
C190.9336 (3)0.0642 (2)0.3935 (2)0.0455 (11)
C201.0388 (3)0.0524 (3)0.4190 (3)0.0712 (15)
H20A1.07740.06640.38540.107*
H20B1.04990.00050.43050.107*
H20C1.05690.08360.45760.107*
C211.0570 (4)0.5592 (3)0.7408 (3)0.0678 (14)
H211.00180.58930.74170.081*
C221.1443 (5)0.5828 (3)0.7750 (3)0.0867 (18)
H221.14730.62820.79900.104*
C231.2264 (5)0.5408 (4)0.7742 (3)0.105 (2)
H231.28570.55770.79680.126*
C241.2208 (4)0.4735 (4)0.7399 (4)0.142 (4)
H241.27640.44370.73980.171*
C251.1329 (4)0.4497 (4)0.7052 (4)0.108 (2)
H251.13020.40410.68150.129*
C261.0491 (3)0.4922 (3)0.7051 (2)0.0522 (12)
C270.9549 (3)0.4678 (2)0.6698 (2)0.0463 (11)
C280.8646 (3)0.5012 (3)0.6625 (2)0.0571 (13)
H280.84910.54800.68020.069*
C290.8006 (3)0.4529 (2)0.6241 (2)0.0499 (11)
C300.6931 (3)0.4608 (3)0.6028 (3)0.0749 (16)
H30A0.67570.43740.56010.112*
H30B0.67600.51410.60010.112*
H30C0.65860.43600.63450.112*
C310.3854 (5)0.1563 (5)0.5683 (4)0.138 (3)
H310.37970.18020.60840.166*
C320.3057 (6)0.1176 (7)0.5348 (6)0.156 (4)
H320.24680.11690.55170.187*
C330.3140 (8)0.0807 (6)0.4775 (7)0.166 (5)
H330.26160.05290.45580.199*
C340.3981 (6)0.0844 (6)0.4519 (5)0.176 (4)
H340.40320.06030.41180.211*
C350.4776 (5)0.1240 (5)0.4853 (5)0.140 (3)
H350.53550.12590.46720.168*
C360.4724 (4)0.1602 (4)0.5438 (4)0.0803 (18)
C370.5561 (4)0.2010 (3)0.5797 (3)0.0625 (14)
C380.5858 (4)0.2149 (3)0.6456 (3)0.0786 (17)
H380.55310.20060.68050.094*
C390.6743 (4)0.2547 (3)0.6508 (2)0.0597 (13)
C400.7380 (5)0.2824 (3)0.7117 (2)0.0892 (19)
H40A0.80500.28190.70430.134*
H40B0.73050.24950.74830.134*
H40C0.71960.33370.72160.134*
C410.9313 (4)0.3916 (2)0.4734 (2)0.0634 (13)
H41A0.87260.42100.47290.095*
H41B0.94440.38450.42890.095*
H41C0.98490.41830.49870.095*
C420.8036 (3)0.1299 (2)0.5335 (2)0.0563 (12)
H42A0.76120.10010.50180.084*
H42B0.77470.13540.57330.084*
H42C0.86550.10450.54360.084*
N10.6971 (3)0.2664 (2)0.59041 (17)0.0473 (9)
N20.8477 (2)0.3908 (2)0.60875 (17)0.0466 (9)
N31.0426 (2)0.2502 (2)0.42132 (17)0.0481 (9)
N40.8888 (2)0.12950 (19)0.40318 (17)0.0449 (9)
N50.6243 (3)0.2336 (2)0.5482 (2)0.0530 (11)
N60.9418 (3)0.4019 (2)0.63658 (19)0.0497 (10)
N71.1142 (3)0.2828 (2)0.4645 (2)0.0515 (10)
N80.7954 (3)0.1194 (2)0.3738 (2)0.0487 (11)
O10.91953 (19)0.31904 (14)0.50286 (13)0.0421 (7)
O20.81754 (18)0.20320 (14)0.50649 (13)0.0388 (6)
O30.6912 (2)0.35140 (18)0.44912 (16)0.0700 (10)
O40.7729 (3)0.2916 (2)0.36896 (16)0.0741 (10)
O50.6229 (3)0.3515 (3)0.3371 (2)0.1208 (17)
O60.6324 (3)0.2375 (2)0.39973 (18)0.0806 (11)
O71.1032 (2)0.28455 (17)0.61243 (16)0.0623 (9)
O80.9631 (2)0.22786 (18)0.64244 (15)0.0600 (8)
O91.0497 (2)0.16613 (17)0.56659 (15)0.0612 (9)
O101.1167 (3)0.17362 (19)0.67927 (16)0.0747 (10)
Cl10.67889 (10)0.30902 (7)0.38767 (6)0.0641 (4)
Cl21.05868 (8)0.21234 (6)0.62539 (5)0.0481 (3)
Cu10.92039 (4)0.22382 (3)0.45477 (2)0.04138 (16)
Cu20.81615 (4)0.29804 (3)0.55465 (2)0.04131 (16)
H431.107 (3)0.283 (3)0.502 (2)0.056 (16)*
H440.983 (3)0.372 (2)0.6319 (17)0.026 (11)*
H450.762 (3)0.149 (2)0.3770 (19)0.028 (13)*
H460.628 (3)0.231 (3)0.512 (2)0.053 (17)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.114 (6)0.194 (9)0.118 (6)0.086 (6)0.017 (5)0.001 (6)
C20.053 (5)0.170 (10)0.214 (12)0.032 (6)0.024 (6)0.066 (8)
C30.040 (4)0.101 (6)0.245 (12)0.007 (4)0.016 (6)0.055 (7)
C40.055 (4)0.076 (4)0.217 (9)0.004 (3)0.029 (5)0.039 (5)
C50.044 (3)0.076 (4)0.109 (5)0.008 (3)0.011 (3)0.027 (4)
C60.079 (5)0.163 (7)0.105 (6)0.065 (5)0.010 (4)0.004 (5)
C70.045 (3)0.063 (3)0.077 (4)0.007 (2)0.022 (3)0.018 (3)
C80.088 (4)0.067 (4)0.081 (4)0.002 (3)0.053 (3)0.008 (3)
C90.086 (4)0.053 (3)0.044 (3)0.003 (3)0.018 (3)0.005 (2)
C100.163 (6)0.101 (5)0.036 (3)0.027 (4)0.012 (4)0.003 (3)
C110.054 (4)0.093 (5)0.156 (6)0.005 (3)0.015 (4)0.068 (4)
C120.057 (4)0.121 (6)0.222 (9)0.003 (4)0.025 (5)0.076 (6)
C130.070 (4)0.119 (6)0.129 (6)0.034 (4)0.010 (4)0.042 (5)
C140.095 (5)0.077 (4)0.094 (5)0.038 (4)0.000 (4)0.035 (4)
C150.070 (4)0.069 (4)0.078 (4)0.017 (3)0.002 (3)0.025 (3)
C160.053 (3)0.049 (3)0.059 (3)0.015 (2)0.001 (2)0.014 (2)
C170.053 (3)0.037 (2)0.044 (3)0.007 (2)0.004 (2)0.007 (2)
C180.060 (3)0.036 (3)0.065 (3)0.004 (2)0.002 (2)0.012 (2)
C190.044 (3)0.042 (3)0.048 (3)0.005 (2)0.000 (2)0.006 (2)
C200.057 (3)0.064 (3)0.087 (4)0.017 (3)0.008 (3)0.008 (3)
C210.067 (3)0.060 (3)0.075 (4)0.006 (3)0.006 (3)0.022 (3)
C220.088 (5)0.078 (4)0.090 (4)0.023 (4)0.002 (4)0.038 (3)
C230.064 (4)0.128 (6)0.118 (5)0.035 (4)0.003 (4)0.054 (5)
C240.049 (4)0.143 (7)0.227 (9)0.002 (4)0.007 (5)0.114 (7)
C250.052 (4)0.099 (5)0.166 (7)0.002 (3)0.003 (4)0.080 (5)
C260.050 (3)0.049 (3)0.058 (3)0.008 (2)0.008 (2)0.017 (2)
C270.048 (3)0.042 (3)0.048 (3)0.002 (2)0.006 (2)0.009 (2)
C280.056 (3)0.040 (3)0.074 (3)0.009 (2)0.004 (3)0.019 (2)
C290.049 (3)0.045 (3)0.055 (3)0.007 (2)0.002 (2)0.005 (2)
C300.059 (3)0.067 (3)0.093 (4)0.016 (3)0.008 (3)0.013 (3)
C310.079 (5)0.192 (9)0.146 (7)0.037 (5)0.028 (5)0.055 (6)
C320.060 (5)0.189 (11)0.216 (12)0.048 (6)0.007 (7)0.067 (9)
C330.089 (7)0.148 (9)0.246 (14)0.055 (6)0.021 (9)0.034 (9)
C340.103 (6)0.212 (11)0.205 (10)0.082 (7)0.005 (7)0.065 (8)
C350.075 (5)0.170 (8)0.174 (8)0.055 (5)0.012 (5)0.048 (7)
C360.042 (3)0.082 (4)0.116 (5)0.010 (3)0.008 (3)0.030 (4)
C370.049 (3)0.068 (3)0.073 (4)0.001 (3)0.016 (3)0.020 (3)
C380.074 (4)0.095 (4)0.074 (4)0.002 (3)0.032 (3)0.024 (3)
C390.070 (3)0.065 (3)0.045 (3)0.008 (3)0.012 (3)0.009 (2)
C400.125 (5)0.103 (5)0.040 (3)0.001 (4)0.011 (3)0.006 (3)
C410.071 (3)0.041 (3)0.079 (4)0.011 (2)0.014 (3)0.004 (2)
C420.061 (3)0.041 (3)0.066 (3)0.006 (2)0.004 (2)0.006 (2)
N10.048 (2)0.057 (2)0.038 (2)0.0045 (18)0.0074 (17)0.0015 (18)
N20.040 (2)0.048 (2)0.050 (2)0.0016 (17)0.0012 (17)0.0106 (17)
N30.046 (2)0.058 (2)0.041 (2)0.0086 (18)0.0082 (18)0.0062 (18)
N40.035 (2)0.046 (2)0.051 (2)0.0014 (16)0.0033 (17)0.0119 (17)
N50.047 (2)0.062 (3)0.050 (3)0.0082 (19)0.008 (2)0.003 (2)
N60.039 (2)0.041 (2)0.067 (3)0.0070 (19)0.003 (2)0.0185 (19)
N70.043 (2)0.070 (3)0.043 (3)0.0155 (19)0.012 (2)0.002 (2)
N80.039 (2)0.040 (2)0.063 (3)0.0051 (19)0.0055 (19)0.017 (2)
O10.0455 (17)0.0345 (16)0.0464 (17)0.0067 (13)0.0071 (13)0.0025 (13)
O20.0406 (16)0.0321 (15)0.0427 (16)0.0039 (12)0.0022 (13)0.0004 (12)
O30.082 (2)0.060 (2)0.069 (2)0.0104 (18)0.0119 (19)0.0156 (18)
O40.086 (3)0.087 (3)0.051 (2)0.027 (2)0.0145 (19)0.0009 (18)
O50.140 (4)0.122 (4)0.089 (3)0.055 (3)0.020 (3)0.038 (3)
O60.090 (3)0.067 (2)0.078 (3)0.009 (2)0.012 (2)0.009 (2)
O70.068 (2)0.0473 (19)0.070 (2)0.0116 (16)0.0054 (18)0.0071 (16)
O80.062 (2)0.070 (2)0.0490 (19)0.0081 (17)0.0131 (16)0.0004 (16)
O90.075 (2)0.056 (2)0.0518 (19)0.0008 (17)0.0075 (16)0.0175 (16)
O100.092 (3)0.066 (2)0.059 (2)0.027 (2)0.0120 (19)0.0032 (18)
Cl10.0831 (9)0.0561 (8)0.0482 (7)0.0204 (7)0.0069 (6)0.0045 (6)
Cl20.0587 (7)0.0424 (6)0.0413 (6)0.0062 (5)0.0008 (5)0.0058 (5)
Cu10.0388 (3)0.0408 (3)0.0432 (3)0.0056 (2)0.0013 (2)0.0087 (2)
Cu20.0413 (3)0.0400 (3)0.0414 (3)0.0044 (2)0.0020 (2)0.0067 (2)
Geometric parameters (Å, º) top
C1—C21.351 (11)C30—H30B0.9600
C1—C61.391 (8)C30—H30C0.9600
C1—H10.9300C31—C361.372 (8)
C2—C31.363 (12)C31—C321.386 (11)
C2—H20.9300C31—H310.9300
C3—C41.402 (10)C32—C331.353 (13)
C3—H30.9300C32—H320.9300
C4—C51.369 (7)C33—C341.344 (12)
C4—H40.9300C33—H330.9300
C5—C61.386 (9)C34—C351.391 (9)
C5—C71.481 (7)C34—H340.9300
C6—H60.9300C35—C361.360 (9)
C7—N71.334 (6)C35—H350.9300
C7—C81.368 (7)C36—C371.462 (8)
C8—C91.391 (7)C37—N51.343 (6)
C8—H80.9300C37—C381.367 (7)
C9—N31.329 (5)C38—C391.399 (7)
C9—C101.473 (7)C38—H380.9300
C10—H10A0.9600C39—N11.330 (5)
C10—H10B0.9600C39—C401.495 (7)
C10—H10C0.9600C40—H40A0.9600
C11—C161.352 (7)C40—H40B0.9600
C11—C121.388 (7)C40—H40C0.9600
C11—H110.9300C41—O11.421 (5)
C12—C131.350 (9)C41—H41A0.9600
C12—H120.9300C41—H41B0.9600
C13—C141.346 (8)C41—H41C0.9600
C13—H130.9300C42—O21.418 (5)
C14—C151.375 (7)C42—H42A0.9600
C14—H140.9300C42—H42B0.9600
C15—C161.367 (6)C42—H42C0.9600
C15—H150.9300N1—N51.354 (5)
C16—C171.470 (6)N1—Cu21.975 (3)
C17—N81.329 (5)N2—N61.357 (5)
C17—C181.367 (6)N2—Cu21.973 (3)
C18—C191.380 (6)N3—N71.353 (5)
C18—H180.9300N3—Cu11.968 (3)
C19—N41.325 (5)N4—N81.356 (5)
C19—C201.488 (6)N4—Cu11.969 (3)
C20—H20A0.9600N5—H460.75 (4)
C20—H20B0.9600N6—H440.80 (3)
C20—H20C0.9600N7—H430.78 (4)
C21—C221.367 (7)N8—H450.70 (4)
C21—C261.374 (6)O1—Cu11.931 (3)
C21—H210.9300O1—Cu21.932 (3)
C22—C231.354 (8)O2—Cu11.924 (3)
C22—H220.9300O2—Cu21.926 (2)
C23—C241.364 (8)O3—Cl11.443 (3)
C23—H230.9300O3—Cu22.722 (3)
C24—C251.380 (7)O4—Cl11.441 (4)
C24—H240.9300O4—Cu12.755 (3)
C25—C261.376 (6)O5—Cl11.407 (4)
C25—H250.9300O6—Cl11.441 (4)
C26—C271.458 (6)O7—Cl21.444 (3)
C27—N61.334 (5)O8—Cl21.441 (3)
C27—C281.367 (6)O8—Cu22.790 (3)
C28—C291.382 (6)O9—Cl21.435 (3)
C28—H280.9300O9—Cu12.869 (3)
C29—N21.325 (5)O10—Cl21.433 (3)
C29—C301.495 (6)Cu1—Cu22.9583 (7)
C30—H30A0.9600
C2—C1—C6117.7 (9)C31—C36—C37121.0 (7)
C2—C1—H1121.1N5—C37—C38105.2 (5)
C6—C1—H1121.1N5—C37—C36121.8 (5)
C1—C2—C3123.9 (9)C38—C37—C36133.0 (5)
C1—C2—H2118.0C37—C38—C39107.4 (5)
C3—C2—H2118.0C37—C38—H38126.3
C2—C3—C4117.5 (8)C39—C38—H38126.3
C2—C3—H3121.2N1—C39—C38109.1 (5)
C4—C3—H3121.2N1—C39—C40121.8 (5)
C5—C4—C3120.7 (8)C38—C39—C40129.0 (5)
C5—C4—H4119.6C39—C40—H40A109.5
C3—C4—H4119.6C39—C40—H40B109.5
C4—C5—C6119.1 (6)H40A—C40—H40B109.5
C4—C5—C7120.7 (7)C39—C40—H40C109.5
C6—C5—C7120.0 (5)H40A—C40—H40C109.5
C5—C6—C1120.9 (7)H40B—C40—H40C109.5
C5—C6—H6119.5O1—C41—H41A109.5
C1—C6—H6119.5O1—C41—H41B109.5
N7—C7—C8104.2 (5)H41A—C41—H41B109.5
N7—C7—C5121.6 (5)O1—C41—H41C109.5
C8—C7—C5134.1 (5)H41A—C41—H41C109.5
C7—C8—C9108.3 (4)H41B—C41—H41C109.5
C7—C8—H8125.9O2—C42—H42A109.5
C9—C8—H8125.9O2—C42—H42B109.5
N3—C9—C8108.6 (4)H42A—C42—H42B109.5
N3—C9—C10121.6 (5)O2—C42—H42C109.5
C8—C9—C10129.8 (5)H42A—C42—H42C109.5
C9—C10—H10A109.5H42B—C42—H42C109.5
C9—C10—H10B109.5C39—N1—N5105.6 (4)
H10A—C10—H10B109.5C39—N1—Cu2135.0 (3)
C9—C10—H10C109.5N5—N1—Cu2117.9 (3)
H10A—C10—H10C109.5C29—N2—N6105.1 (3)
H10B—C10—H10C109.5C29—N2—Cu2136.6 (3)
C16—C11—C12121.5 (5)N6—N2—Cu2118.2 (3)
C16—C11—H11119.3C9—N3—N7105.4 (4)
C12—C11—H11119.3C9—N3—Cu1137.1 (3)
C13—C12—C11119.8 (6)N7—N3—Cu1117.3 (3)
C13—C12—H12120.1C19—N4—N8105.1 (3)
C11—C12—H12120.1C19—N4—Cu1136.6 (3)
C14—C13—C12119.5 (6)N8—N4—Cu1117.9 (3)
C14—C13—H13120.2C37—N5—N1112.6 (4)
C12—C13—H13120.2C37—N5—H46127 (4)
C13—C14—C15120.4 (6)N1—N5—H46120 (4)
C13—C14—H14119.8C27—N6—N2112.7 (4)
C15—C14—H14119.8C27—N6—H44126 (3)
C16—C15—C14121.3 (6)N2—N6—H44121 (3)
C16—C15—H15119.3C7—N7—N3113.4 (4)
C14—C15—H15119.3C7—N7—H43130 (4)
C11—C16—C15117.4 (5)N3—N7—H43116 (3)
C11—C16—C17122.2 (4)C17—N8—N4112.7 (4)
C15—C16—C17120.4 (5)C17—N8—H45129 (3)
N8—C17—C18105.2 (4)N4—N8—H45118 (3)
N8—C17—C16122.8 (4)C41—O1—Cu1123.0 (3)
C18—C17—C16132.0 (4)C41—O1—Cu2122.6 (3)
C17—C18—C19107.4 (4)Cu1—O1—Cu299.97 (11)
C17—C18—H18126.3C42—O2—Cu1122.3 (2)
C19—C18—H18126.3C42—O2—Cu2124.5 (3)
N4—C19—C18109.6 (4)Cu1—O2—Cu2100.42 (11)
N4—C19—C20121.5 (4)Cl1—O3—Cu2119.47 (17)
C18—C19—C20128.9 (4)Cl1—O4—Cu1122.49 (18)
C19—C20—H20A109.5Cl2—O8—Cu2122.50 (16)
C19—C20—H20B109.5Cl2—O9—Cu1115.77 (17)
H20A—C20—H20B109.5O5—Cl1—O4109.9 (2)
C19—C20—H20C109.5O5—Cl1—O6111.7 (3)
H20A—C20—H20C109.5O4—Cl1—O6107.7 (2)
H20B—C20—H20C109.5O5—Cl1—O3110.4 (3)
C22—C21—C26121.6 (5)O4—Cl1—O3109.9 (2)
C22—C21—H21119.2O6—Cl1—O3107.2 (2)
C26—C21—H21119.2O10—Cl2—O9110.2 (2)
C23—C22—C21120.8 (5)O10—Cl2—O8109.6 (2)
C23—C22—H22119.6O9—Cl2—O8109.57 (19)
C21—C22—H22119.6O10—Cl2—O7110.2 (2)
C22—C23—C24119.1 (5)O9—Cl2—O7109.0 (2)
C22—C23—H23120.4O8—Cl2—O7108.08 (19)
C24—C23—H23120.4O2—Cu1—O179.85 (11)
C23—C24—C25120.2 (6)O2—Cu1—N3167.14 (13)
C23—C24—H24119.9O1—Cu1—N392.45 (13)
C25—C24—H24119.9O2—Cu1—N490.65 (13)
C26—C25—C24121.3 (5)O1—Cu1—N4166.97 (13)
C26—C25—H25119.4N3—Cu1—N498.42 (14)
C24—C25—H25119.4O2—Cu1—O483.65 (11)
C21—C26—C25117.1 (4)O1—Cu1—O483.90 (11)
C21—C26—C27120.5 (4)N3—Cu1—O4105.91 (13)
C25—C26—C27122.5 (4)N4—Cu1—O486.20 (12)
N6—C27—C28104.9 (4)O2—Cu1—O985.70 (10)
N6—C27—C26123.2 (4)O1—Cu1—O987.03 (10)
C28—C27—C26131.8 (4)N3—Cu1—O983.62 (12)
C27—C28—C29107.6 (4)N4—Cu1—O9101.25 (12)
C27—C28—H28126.2O4—Cu1—O9167.07 (9)
C29—C28—H28126.2O2—Cu1—Cu239.82 (7)
N2—C29—C28109.6 (4)O1—Cu1—Cu240.03 (8)
N2—C29—C30120.6 (4)N3—Cu1—Cu2131.67 (10)
C28—C29—C30129.7 (4)N4—Cu1—Cu2129.88 (10)
C29—C30—H30A109.5O4—Cu1—Cu281.86 (7)
C29—C30—H30B109.5O9—Cu1—Cu285.27 (6)
H30A—C30—H30B109.5O2—Cu2—O179.76 (11)
C29—C30—H30C109.5O2—Cu2—N2166.64 (13)
H30A—C30—H30C109.5O1—Cu2—N291.59 (13)
H30B—C30—H30C109.5O2—Cu2—N191.03 (13)
C36—C31—C32121.5 (9)O1—Cu2—N1168.03 (13)
C36—C31—H31119.3N2—Cu2—N198.78 (14)
C32—C31—H31119.3O2—Cu2—O386.78 (10)
C33—C32—C31119.8 (10)O1—Cu2—O386.53 (11)
C33—C32—H32120.1N2—Cu2—O3102.96 (12)
C31—C32—H32120.1N1—Cu2—O385.33 (13)
C34—C33—C32119.9 (11)O2—Cu2—O883.63 (10)
C34—C33—H33120.1O1—Cu2—O884.54 (10)
C32—C33—H33120.1N2—Cu2—O885.44 (12)
C33—C34—C35120.2 (10)N1—Cu2—O8102.14 (12)
C33—C34—H34119.9O3—Cu2—O8167.91 (9)
C35—C34—H34119.9O2—Cu2—Cu139.76 (8)
C36—C35—C34121.4 (8)O1—Cu2—Cu140.00 (8)
C36—C35—H35119.3N2—Cu2—Cu1130.82 (10)
C34—C35—H35119.3N1—Cu2—Cu1130.35 (10)
C35—C36—C31117.2 (7)O3—Cu2—Cu185.62 (7)
C35—C36—C37121.8 (6)O8—Cu2—Cu182.30 (6)

Experimental details

Crystal data
Chemical formula[Cu(CH3O)2(C40H40N8)](ClO4)2
Mr1020.85
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)13.8398 (12), 17.4607 (16), 20.3779 (18)
β (°) 98.316 (1)
V3)4872.6 (8)
Z4
Radiation typeMo Kα
µ (mm1)1.04
Crystal size (mm)0.15 × 0.13 × 0.11
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2006)
Tmin, Tmax0.859, 0.894
No. of measured, independent and
observed [I > 2σ(I)] reflections
48197, 9045, 5370
Rint0.074
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.137, 1.00
No. of reflections9045
No. of parameters599
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.46, 0.26

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Sheldrick, 1997b) and publCIF (Version 1.0_c; Westrip, 2007).

 

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