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The title complex, [Cu(C4H6N2)(C6H18N4)](ClO4)2 or [Cu(Melm)(tren)](ClO4)2 [Melm = N-methyl­imidazole and tren = tris­(2-amino­ethyl)amine], contains two [Cu(MeIm)(tren)]2+ cations in the asymmetric unit with slightly different bond distances and angles. The coordination geometry of the CuII ion is distorted trigonal–bipyramidal, with three primary amine groups of the tren ligand forming the equatorial plane. The tertiary amine group and the 1-methyl­imidazole are in the axial positions. Intra- and inter­molecular N—H...O hydrogen bonds are observed in the crystal structure, which is stabilized by these N—H...O hydrogen bonds and also weak intra- and inter­molecular C—H...O inter­actions. Crystals of the title complex are twinned.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806016333/ww2013sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806016333/ww2013Isup2.hkl
Contains datablock I

CCDC reference: 610926

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.049
  • wR factor = 0.137
  • Data-to-parameter ratio = 19.1

checkCIF/PLATON results

No syntax errors found



Alert level B SYMMS02_ALERT_1_B The unit-cell lengths a and c should not be equal for a monoclinic cell Cell 21.9941 7.8942 21.9941 Angles 90.0000 92.6070 90.0000 PLAT725_ALERT_1_B D-H Calc 0.93000, Rep 0.96000 Dev... 0.03 Ang. C8 -H8A 1.555 1.555
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent ......... 1 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.62 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.19 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C19 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N6 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl2 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl3 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C10 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 Cl O4
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

(1-Methylimidazole-κN3)[tris(2-aminoethyl)amine-κ4N]copper(II) bis(perchlorate) top
Crystal data top
[Cu(C4H6N2)(C6H18N4)](ClO4)2F(000) = 2024
Mr = 490.80Dx = 1.709 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9198 reflections
a = 21.9941 (7) Åθ = 0.9–28.0°
b = 7.8942 (3) ŵ = 1.48 mm1
c = 21.9941 (7) ÅT = 100 K
β = 92.607 (2)°Needle, blue
V = 3814.8 (2) Å30.43 × 0.13 × 0.10 mm
Z = 8
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
9198 independent reflections
Radiation source: fine-focus sealed tube7032 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
Detector resolution: 8.33 pixels mm-1θmax = 28.0°, θmin = 0.9°
ω scansh = 2929
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1010
Tmin = 0.794, Tmax = 0.863l = 2929
41516 measured reflections
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-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0788P)2]
where P = (Fo2 + 2Fc2)/3
9198 reflections(Δ/σ)max = 0.001
482 parametersΔρmax = 0.89 e Å3
0 restraintsΔρmin = 1.04 e Å3
Special details top

Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment

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 > 2σ(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
Cu10.80503 (3)0.28293 (7)0.09078 (3)0.01641 (16)
Cu20.41389 (3)0.26543 (11)0.19407 (3)0.01780 (16)
Cl10.58046 (5)0.20466 (15)0.16556 (5)0.0186 (3)
Cl20.18146 (7)0.2578 (2)0.37160 (7)0.0307 (3)
Cl30.62822 (6)0.30378 (16)0.32509 (6)0.0283 (3)
Cl40.16773 (6)0.23126 (18)0.08051 (6)0.0207 (3)*
O10.64587 (16)0.1984 (5)0.16405 (18)0.0268 (9)
O20.55809 (16)0.3546 (5)0.13348 (16)0.0267 (8)
O30.55468 (16)0.0559 (5)0.13609 (15)0.0271 (8)
O40.56218 (17)0.2102 (5)0.22727 (17)0.0278 (9)
O50.1227 (2)0.1779 (6)0.3626 (3)0.0656 (15)
O60.1869 (3)0.3179 (7)0.4322 (2)0.0692 (16)
O70.18419 (19)0.3978 (6)0.33091 (18)0.0483 (11)
O80.2287 (2)0.1380 (5)0.3602 (2)0.0553 (13)
O90.6139 (3)0.3699 (7)0.3828 (2)0.0781 (17)
O100.6379 (2)0.4376 (5)0.2838 (2)0.0668 (15)
O110.6813 (2)0.2039 (6)0.3305 (2)0.0616 (15)
O120.5788 (3)0.2029 (8)0.3036 (3)0.094 (2)
O130.14142 (16)0.3815 (5)0.05278 (16)0.0327 (9)
O140.13402 (16)0.0836 (5)0.05867 (16)0.0327 (9)
O150.1641 (2)0.2437 (5)0.14492 (17)0.0296 (9)
O160.23062 (16)0.2167 (5)0.06429 (17)0.0249 (9)
N10.71605 (19)0.2604 (5)0.11379 (19)0.0176 (9)
N20.77521 (18)0.5185 (5)0.0519 (2)0.0279 (10)
H2C0.78730.60540.07600.033*
H2D0.79060.53310.01510.033*
N30.78554 (19)0.0692 (6)0.0397 (2)0.0354 (12)
H3C0.77920.09720.00030.042*
H3D0.81690.00390.04290.042*
N40.8237 (2)0.3013 (6)0.1829 (2)0.0285 (11)
H4C0.84470.20950.19610.034*
H4D0.84670.39360.19100.034*
N50.89156 (19)0.2943 (5)0.0689 (2)0.0226 (10)
N60.9739 (2)0.2658 (6)0.0164 (2)0.0277 (11)
N70.38823 (18)0.2918 (5)0.28151 (19)0.0175 (9)
N80.4409 (2)0.0183 (5)0.22279 (18)0.0256 (10)
H8B0.41550.05960.20590.031*
H8C0.47880.00390.21130.031*
N90.3215 (2)0.2883 (6)0.1731 (2)0.0257 (10)
H9B0.31440.38390.15170.031*
H9C0.30880.20000.14990.031*
N100.4810 (2)0.4414 (6)0.22050 (18)0.0350 (11)
H10D0.51620.38850.23070.042*
H10E0.48740.51430.19000.042*
N110.4380 (2)0.2445 (5)0.1085 (2)0.0216 (10)
N120.4906 (2)0.2548 (5)0.0264 (2)0.0245 (10)
C10.6860 (2)0.4279 (6)0.1039 (2)0.0254 (11)
H1A0.69540.50100.13840.030*
H1B0.64220.41290.10040.030*
C20.7077 (2)0.5095 (7)0.0465 (3)0.0311 (13)
H2A0.69480.44280.01120.037*
H2B0.69070.62240.04190.037*
C30.6854 (2)0.1307 (6)0.0752 (2)0.0214 (10)
H3A0.67060.18090.03710.026*
H3B0.65090.08450.09560.026*
C40.7306 (2)0.0091 (6)0.0629 (2)0.0265 (12)
H4A0.74070.07100.10010.032*
H4B0.71300.08790.03310.032*
C50.7169 (2)0.2113 (7)0.1787 (2)0.0251 (11)
H5A0.72590.09150.18270.030*
H5B0.67720.23180.19480.030*
C60.7651 (2)0.3140 (8)0.2147 (2)0.0325 (14)
H6A0.75250.43150.21720.039*
H6B0.77040.26970.25580.039*
C70.9133 (2)0.2554 (8)0.0160 (3)0.0356 (16)
H7A0.88920.22410.01800.043*
C80.9927 (3)0.3164 (9)0.0729 (3)0.0485 (18)
H8A1.03250.33670.08700.058*
C90.9418 (3)0.3317 (9)0.1047 (3)0.0488 (18)
H9A0.94120.36340.14540.059*
C101.0134 (3)0.2264 (10)0.0334 (3)0.055 (2)
H10A0.98890.19330.06870.083*
H10B1.04030.13540.02150.083*
H10C1.03680.32480.04290.083*
C110.3859 (2)0.1196 (6)0.3085 (2)0.0242 (11)
H11A0.34800.06510.29550.029*
H11B0.38710.12850.35250.029*
C120.4389 (2)0.0126 (7)0.2893 (2)0.0267 (12)
H12A0.47670.05620.30770.032*
H12B0.43390.10340.30270.032*
C130.3266 (2)0.3730 (7)0.2784 (2)0.0273 (12)
H13A0.33060.49330.27060.033*
H13B0.30750.35900.31690.033*
C140.2876 (2)0.2927 (8)0.2283 (3)0.0286 (13)
H14A0.27650.17850.23980.034*
H14B0.25050.35770.22130.034*
C150.4332 (2)0.3996 (6)0.3155 (2)0.0232 (11)
H15A0.46630.33000.33200.028*
H15B0.41390.45400.34920.028*
C160.4579 (3)0.5327 (7)0.2739 (2)0.0323 (13)
H16A0.42600.61160.26110.039*
H16B0.49050.59550.29480.039*
C170.4896 (3)0.2921 (7)0.0857 (2)0.0269 (13)
H17A0.52120.34480.10790.032*
C180.4376 (3)0.1752 (8)0.0108 (3)0.0399 (15)
H18A0.42560.13310.02740.048*
C190.4056 (3)0.1689 (9)0.0618 (3)0.0465 (17)
H19A0.36730.12030.06460.056*
C200.5413 (3)0.2914 (8)0.0136 (3)0.0348 (15)
H20A0.57270.35190.00910.052*
H20B0.52660.35920.04740.052*
H20C0.55740.18700.02830.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0163 (3)0.0151 (3)0.0180 (3)0.0007 (2)0.0019 (2)0.0002 (2)
Cu20.0215 (3)0.0164 (4)0.0157 (3)0.0001 (3)0.0030 (2)0.0002 (2)
Cl10.0168 (5)0.0175 (6)0.0218 (6)0.0009 (5)0.0032 (4)0.0007 (5)
Cl20.0419 (8)0.0229 (6)0.0283 (7)0.0007 (6)0.0136 (6)0.0002 (6)
Cl30.0256 (7)0.0231 (7)0.0369 (7)0.0009 (6)0.0087 (5)0.0026 (6)
O10.0170 (18)0.028 (2)0.036 (2)0.0007 (17)0.0058 (15)0.0003 (18)
O20.0280 (19)0.0226 (19)0.0297 (19)0.0096 (17)0.0037 (15)0.0045 (17)
O30.0311 (19)0.0222 (19)0.0283 (19)0.0076 (17)0.0053 (15)0.0056 (16)
O40.028 (2)0.033 (2)0.023 (2)0.0003 (17)0.0037 (15)0.0014 (17)
O50.049 (3)0.048 (3)0.102 (4)0.013 (3)0.031 (3)0.014 (3)
O60.102 (4)0.076 (4)0.031 (2)0.009 (3)0.006 (2)0.010 (3)
O70.050 (3)0.051 (3)0.045 (2)0.009 (2)0.011 (2)0.021 (2)
O80.061 (3)0.029 (2)0.079 (3)0.003 (2)0.031 (2)0.001 (2)
O90.108 (4)0.077 (4)0.053 (3)0.011 (4)0.050 (3)0.018 (3)
O100.114 (4)0.026 (2)0.064 (3)0.009 (3)0.040 (3)0.014 (2)
O110.055 (3)0.072 (4)0.059 (3)0.036 (3)0.018 (2)0.028 (3)
O120.047 (3)0.121 (5)0.113 (5)0.050 (4)0.000 (3)0.025 (4)
O130.031 (2)0.032 (2)0.035 (2)0.0059 (18)0.0025 (16)0.0162 (19)
O140.034 (2)0.034 (2)0.031 (2)0.0155 (19)0.0068 (16)0.0086 (18)
O150.042 (2)0.030 (2)0.0168 (19)0.0006 (18)0.0050 (16)0.0027 (16)
O160.0183 (18)0.032 (2)0.025 (2)0.0004 (16)0.0035 (14)0.0042 (17)
N10.020 (2)0.015 (2)0.018 (2)0.0041 (17)0.0001 (16)0.0013 (17)
N20.029 (2)0.022 (2)0.033 (2)0.001 (2)0.0031 (18)0.006 (2)
N30.025 (2)0.030 (3)0.052 (3)0.007 (2)0.014 (2)0.016 (2)
N40.023 (2)0.037 (3)0.025 (2)0.006 (2)0.0004 (18)0.001 (2)
N50.019 (2)0.019 (2)0.030 (2)0.0026 (19)0.0048 (17)0.002 (2)
N60.022 (2)0.040 (3)0.022 (2)0.005 (2)0.0086 (18)0.002 (2)
N70.017 (2)0.015 (2)0.020 (2)0.0027 (17)0.0040 (16)0.0006 (17)
N80.035 (2)0.019 (2)0.023 (2)0.007 (2)0.0051 (17)0.0011 (19)
N90.028 (2)0.026 (2)0.022 (2)0.005 (2)0.0049 (18)0.001 (2)
N100.046 (3)0.035 (3)0.024 (2)0.016 (2)0.0068 (19)0.002 (2)
N110.028 (2)0.018 (2)0.019 (2)0.0035 (18)0.0020 (17)0.0003 (17)
N120.031 (3)0.025 (2)0.017 (2)0.006 (2)0.0032 (18)0.0005 (19)
C10.020 (2)0.018 (3)0.038 (3)0.007 (2)0.003 (2)0.004 (2)
C20.027 (3)0.016 (3)0.050 (3)0.004 (2)0.008 (2)0.006 (3)
C30.023 (2)0.015 (2)0.026 (3)0.008 (2)0.0003 (19)0.003 (2)
C40.030 (3)0.013 (2)0.036 (3)0.008 (2)0.006 (2)0.007 (2)
C50.024 (3)0.035 (3)0.016 (2)0.004 (2)0.0052 (18)0.004 (2)
C60.029 (3)0.054 (4)0.015 (3)0.007 (3)0.004 (2)0.004 (3)
C70.019 (3)0.068 (4)0.020 (3)0.007 (3)0.000 (2)0.001 (3)
C80.018 (3)0.084 (5)0.043 (4)0.004 (3)0.000 (2)0.020 (4)
C90.030 (3)0.085 (5)0.032 (3)0.013 (3)0.007 (2)0.030 (3)
C100.022 (3)0.125 (7)0.020 (3)0.004 (3)0.006 (2)0.016 (3)
C110.031 (3)0.019 (3)0.023 (2)0.003 (2)0.003 (2)0.001 (2)
C120.033 (3)0.019 (3)0.028 (3)0.000 (2)0.006 (2)0.002 (2)
C130.029 (3)0.026 (3)0.027 (3)0.013 (2)0.006 (2)0.003 (2)
C140.023 (3)0.035 (3)0.028 (3)0.004 (3)0.003 (2)0.005 (3)
C150.030 (3)0.019 (2)0.020 (2)0.001 (2)0.0009 (19)0.005 (2)
C160.051 (4)0.021 (3)0.024 (3)0.016 (3)0.000 (2)0.009 (2)
C170.025 (3)0.033 (3)0.023 (3)0.004 (2)0.001 (2)0.000 (2)
C180.050 (4)0.045 (4)0.025 (3)0.025 (3)0.007 (2)0.011 (3)
C190.055 (4)0.061 (4)0.025 (3)0.036 (4)0.007 (3)0.004 (3)
C200.034 (3)0.047 (4)0.024 (3)0.004 (3)0.009 (2)0.003 (3)
Geometric parameters (Å, º) top
Cu1—N51.986 (4)N10—C161.488 (7)
Cu1—N12.051 (4)N10—H10D0.9000
Cu1—N42.053 (5)N10—H10E0.9000
Cu1—N32.061 (5)N11—C171.315 (7)
Cu1—N22.138 (4)N11—C191.360 (7)
Cu2—N111.985 (4)N12—C171.338 (7)
Cu2—N72.039 (4)N12—C181.355 (7)
Cu2—N92.071 (4)N12—C201.478 (7)
Cu2—N102.090 (4)C1—C21.512 (7)
Cu2—N82.127 (4)C1—H1A0.9700
Cl1—O41.434 (4)C1—H1B0.9700
Cl1—O11.441 (4)C2—H2A0.9700
Cl1—O31.445 (4)C2—H2B0.9700
Cl1—O21.453 (4)C3—C41.517 (7)
Cl2—O61.414 (5)C3—H3A0.9700
Cl2—O71.425 (4)C3—H3B0.9700
Cl2—O81.435 (4)C4—H4A0.9700
Cl2—O51.444 (5)C4—H4B0.9700
Cl3—O111.409 (4)C5—C61.527 (7)
Cl3—O121.411 (5)C5—H5A0.9700
Cl3—O101.416 (4)C5—H5B0.9700
Cl3—O91.420 (5)C6—H6A0.9700
Cl4—O151.426 (4)C6—H6B0.9700
Cl4—O131.443 (4)C7—H7A0.9300
Cl4—O161.449 (4)C8—C91.351 (8)
Cl4—O141.452 (4)C8—H8A0.9300
N1—C31.473 (6)C9—H9A0.9300
N1—C51.478 (6)C10—H10A0.9600
N1—C11.490 (6)C10—H10B0.9600
N2—C21.486 (6)C10—H10C0.9600
N2—H2C0.9000C11—C121.516 (7)
N2—H2D0.9000C11—H11A0.9700
N3—C41.470 (6)C11—H11B0.9700
N3—H3C0.9000C12—H12A0.9700
N3—H3D0.9000C12—H12B0.9700
N4—C61.499 (7)C13—C141.505 (7)
N4—H4C0.9000C13—H13A0.9700
N4—H4D0.9000C13—H13B0.9700
N5—C71.314 (7)C14—H14A0.9700
N5—C91.360 (7)C14—H14B0.9700
N6—C71.335 (7)C15—C161.511 (7)
N6—C81.352 (7)C15—H15A0.9700
N6—C101.462 (7)C15—H15B0.9700
N7—C151.481 (6)C16—H16A0.9700
N7—C111.485 (6)C16—H16B0.9700
N7—C131.499 (6)C17—H17A0.9300
N8—C121.466 (6)C18—C191.353 (8)
N8—H8B0.9000C18—H18A0.9300
N8—H8C0.9000C19—H19A0.9300
N9—C141.453 (7)C20—H20A0.9600
N9—H9B0.9000C20—H20B0.9600
N9—H9C0.9000C20—H20C0.9600
N5—Cu1—N1177.58 (17)C18—N12—C20127.1 (5)
N5—Cu1—N494.85 (18)N1—C1—C2110.2 (4)
N1—Cu1—N485.04 (17)N1—C1—H1A109.6
N5—Cu1—N394.74 (17)C2—C1—H1A109.6
N1—Cu1—N383.47 (16)N1—C1—H1B109.6
N4—Cu1—N3128.5 (2)C2—C1—H1B109.6
N5—Cu1—N298.27 (17)H1A—C1—H1B108.1
N1—Cu1—N284.00 (16)N2—C2—C1107.8 (4)
N4—Cu1—N2112.15 (18)N2—C2—H2A110.1
N3—Cu1—N2116.23 (19)C1—C2—H2A110.1
N11—Cu2—N7178.76 (17)N2—C2—H2B110.1
N11—Cu2—N995.63 (18)C1—C2—H2B110.1
N7—Cu2—N983.68 (17)H2A—C2—H2B108.5
N11—Cu2—N1095.92 (17)N1—C3—C4108.8 (4)
N7—Cu2—N1083.81 (16)N1—C3—H3A109.9
N9—Cu2—N10132.62 (19)C4—C3—H3A109.9
N11—Cu2—N897.02 (16)N1—C3—H3B109.9
N7—Cu2—N884.20 (16)C4—C3—H3B109.9
N9—Cu2—N8113.82 (17)H3A—C3—H3B108.3
N10—Cu2—N8110.07 (18)N3—C4—C3108.1 (4)
O4—Cl1—O1110.2 (2)N3—C4—H4A110.1
O4—Cl1—O3109.2 (2)C3—C4—H4A110.1
O1—Cl1—O3109.5 (2)N3—C4—H4B110.1
O4—Cl1—O2109.3 (2)C3—C4—H4B110.1
O1—Cl1—O2109.5 (2)H4A—C4—H4B108.4
O3—Cl1—O2109.1 (2)N1—C5—C6109.9 (4)
O6—Cl2—O7109.1 (3)N1—C5—H5A109.7
O6—Cl2—O8110.8 (3)C6—C5—H5A109.7
O7—Cl2—O8110.5 (3)N1—C5—H5B109.7
O6—Cl2—O5108.2 (3)C6—C5—H5B109.7
O7—Cl2—O5108.4 (3)H5A—C5—H5B108.2
O8—Cl2—O5109.8 (3)N4—C6—C5108.3 (4)
O11—Cl3—O12109.6 (4)N4—C6—H6A110.0
O11—Cl3—O10108.8 (3)C5—C6—H6A110.0
O12—Cl3—O10110.0 (4)N4—C6—H6B110.0
O11—Cl3—O9110.3 (3)C5—C6—H6B110.0
O12—Cl3—O9107.9 (4)H6A—C6—H6B108.4
O10—Cl3—O9110.2 (3)N5—C7—N6112.5 (5)
O15—Cl4—O13108.9 (2)N5—C7—H7A123.7
O15—Cl4—O16110.3 (2)N6—C7—H7A123.7
O13—Cl4—O16109.3 (2)C9—C8—N6106.1 (5)
O15—Cl4—O14109.5 (2)C9—C8—H8A127.0
O13—Cl4—O14109.3 (2)N6—C8—H8A127.0
O16—Cl4—O14109.5 (2)C8—C9—N5110.6 (5)
C3—N1—C5111.1 (4)C8—C9—H9A124.7
C3—N1—C1110.1 (4)N5—C9—H9A124.7
C5—N1—C1111.1 (4)N6—C10—H10A109.5
C3—N1—Cu1109.5 (3)N6—C10—H10B109.5
C5—N1—Cu1106.9 (3)H10A—C10—H10B109.5
C1—N1—Cu1108.0 (3)N6—C10—H10C109.5
C2—N2—Cu1106.1 (3)H10A—C10—H10C109.5
C2—N2—H2C110.5H10B—C10—H10C109.5
Cu1—N2—H2C110.5N7—C11—C12111.0 (4)
C2—N2—H2D110.5N7—C11—H11A109.4
Cu1—N2—H2D110.5C12—C11—H11A109.4
H2C—N2—H2D108.7N7—C11—H11B109.4
C4—N3—Cu1108.0 (3)C12—C11—H11B109.4
C4—N3—H3C110.1H11A—C11—H11B108.0
Cu1—N3—H3C110.1N8—C12—C11108.6 (4)
C4—N3—H3D110.1N8—C12—H12A110.0
Cu1—N3—H3D110.1C11—C12—H12A110.0
H3C—N3—H3D108.4N8—C12—H12B110.0
C6—N4—Cu1109.1 (3)C11—C12—H12B110.0
C6—N4—H4C109.9H12A—C12—H12B108.4
Cu1—N4—H4C109.9N7—C13—C14109.8 (4)
C6—N4—H4D109.9N7—C13—H13A109.7
Cu1—N4—H4D109.9C14—C13—H13A109.7
H4C—N4—H4D108.3N7—C13—H13B109.7
C7—N5—C9104.2 (5)C14—C13—H13B109.7
C7—N5—Cu1126.5 (4)H13A—C13—H13B108.2
C9—N5—Cu1129.2 (4)N9—C14—C13108.9 (4)
C7—N6—C8106.7 (5)N9—C14—H14A109.9
C7—N6—C10127.5 (5)C13—C14—H14A109.9
C8—N6—C10125.8 (5)N9—C14—H14B109.9
C15—N7—C11111.0 (4)C13—C14—H14B109.9
C15—N7—C13111.0 (4)H14A—C14—H14B108.3
C11—N7—C13111.3 (4)N7—C15—C16110.1 (4)
C15—N7—Cu2109.1 (3)N7—C15—H15A109.6
C11—N7—Cu2107.4 (3)C16—C15—H15A109.6
C13—N7—Cu2106.8 (3)N7—C15—H15B109.6
C12—N8—Cu2107.7 (3)C16—C15—H15B109.6
C12—N8—H8B110.2H15A—C15—H15B108.1
Cu2—N8—H8B110.2N10—C16—C15106.7 (4)
C12—N8—H8C110.2N10—C16—H16A110.4
Cu2—N8—H8C110.2C15—C16—H16A110.4
H8B—N8—H8C108.5N10—C16—H16B110.4
C14—N9—Cu2110.6 (3)C15—C16—H16B110.4
C14—N9—H9B109.5H16A—C16—H16B108.6
Cu2—N9—H9B109.5N11—C17—N12111.3 (5)
C14—N9—H9C109.5N11—C17—H17A124.4
Cu2—N9—H9C109.5N12—C17—H17A124.4
H9B—N9—H9C108.1C19—C18—N12106.3 (5)
C16—N10—Cu2106.2 (3)C19—C18—H18A126.8
C16—N10—H10D110.5N12—C18—H18A126.8
Cu2—N10—H10D110.5C18—C19—N11109.6 (5)
C16—N10—H10E110.5C18—C19—H19A125.2
Cu2—N10—H10E110.5N11—C19—H19A125.2
H10D—N10—H10E108.7N12—C20—H20A109.5
C17—N11—C19105.6 (5)N12—C20—H20B109.5
C17—N11—Cu2127.6 (4)H20A—C20—H20B109.5
C19—N11—Cu2126.8 (4)N12—C20—H20C109.5
C17—N12—C18107.2 (5)H20A—C20—H20C109.5
C17—N12—C20125.7 (5)H20B—C20—H20C109.5
N4—Cu1—N1—C3139.4 (3)N9—Cu2—N11—C1933.7 (5)
N3—Cu1—N1—C39.6 (3)N10—Cu2—N11—C19167.7 (5)
N2—Cu1—N1—C3107.7 (3)N8—Cu2—N11—C1981.2 (5)
N4—Cu1—N1—C518.9 (3)C3—N1—C1—C280.2 (5)
N3—Cu1—N1—C5110.8 (3)C5—N1—C1—C2156.3 (4)
N2—Cu1—N1—C5131.8 (3)Cu1—N1—C1—C239.4 (4)
N4—Cu1—N1—C1100.7 (3)Cu1—N2—C2—C141.4 (5)
N3—Cu1—N1—C1129.6 (3)N1—C1—C2—N255.2 (5)
N2—Cu1—N1—C112.2 (3)C5—N1—C3—C482.6 (5)
N5—Cu1—N2—C2162.8 (3)C1—N1—C3—C4153.9 (4)
N1—Cu1—N2—C216.4 (3)Cu1—N1—C3—C435.3 (4)
N4—Cu1—N2—C298.5 (3)Cu1—N3—C4—C342.4 (5)
N3—Cu1—N2—C263.3 (4)N1—C3—C4—N352.0 (5)
N5—Cu1—N3—C4159.9 (4)C3—N1—C5—C6161.9 (4)
N1—Cu1—N3—C418.5 (4)C1—N1—C5—C675.2 (5)
N4—Cu1—N3—C459.8 (4)Cu1—N1—C5—C642.4 (5)
N2—Cu1—N3—C498.5 (4)Cu1—N4—C6—C532.6 (5)
N5—Cu1—N4—C6174.4 (4)N1—C5—C6—N450.5 (6)
N1—Cu1—N4—C68.0 (4)C9—N5—C7—N60.1 (7)
N3—Cu1—N4—C685.6 (4)Cu1—N5—C7—N6176.0 (4)
N2—Cu1—N4—C673.4 (4)C8—N6—C7—N50.7 (7)
N4—Cu1—N5—C7165.4 (5)C10—N6—C7—N5177.8 (6)
N3—Cu1—N5—C736.0 (5)C7—N6—C8—C91.0 (8)
N2—Cu1—N5—C781.4 (5)C10—N6—C8—C9177.6 (7)
N4—Cu1—N5—C99.8 (6)N6—C8—C9—N51.0 (9)
N3—Cu1—N5—C9139.2 (6)C7—N5—C9—C80.6 (8)
N2—Cu1—N5—C9103.4 (6)Cu1—N5—C9—C8176.6 (5)
N9—Cu2—N7—C15140.4 (3)C15—N7—C11—C1278.6 (5)
N10—Cu2—N7—C156.2 (3)C13—N7—C11—C12157.2 (4)
N8—Cu2—N7—C15104.8 (3)Cu2—N7—C11—C1240.6 (4)
N9—Cu2—N7—C1199.1 (3)Cu2—N8—C12—C1135.7 (5)
N10—Cu2—N7—C11126.7 (3)N7—C11—C12—N852.1 (5)
N8—Cu2—N7—C1115.7 (3)C15—N7—C13—C14162.0 (4)
N9—Cu2—N7—C1320.3 (3)C11—N7—C13—C1473.8 (5)
N10—Cu2—N7—C13113.9 (3)Cu2—N7—C13—C1443.1 (5)
N8—Cu2—N7—C13135.1 (3)Cu2—N9—C14—C1330.7 (5)
N11—Cu2—N8—C12168.8 (3)N7—C13—C14—N949.4 (6)
N7—Cu2—N8—C1211.4 (3)C11—N7—C15—C16152.2 (4)
N9—Cu2—N8—C1291.9 (3)C13—N7—C15—C1683.5 (5)
N10—Cu2—N8—C1269.8 (3)Cu2—N7—C15—C1634.0 (5)
N11—Cu2—N9—C14175.3 (4)Cu2—N10—C16—C1545.6 (5)
N7—Cu2—N9—C145.8 (4)N7—C15—C16—N1053.7 (6)
N10—Cu2—N9—C1481.3 (4)C19—N11—C17—N121.9 (7)
N8—Cu2—N9—C1475.0 (4)Cu2—N11—C17—N12178.6 (3)
N11—Cu2—N10—C16156.5 (4)C18—N12—C17—N111.7 (7)
N7—Cu2—N10—C1622.3 (4)C20—N12—C17—N11179.6 (5)
N9—Cu2—N10—C1653.3 (4)C17—N12—C18—C190.8 (7)
N8—Cu2—N10—C16103.8 (3)C20—N12—C18—C19179.5 (6)
N9—Cu2—N11—C17150.2 (5)N12—C18—C19—N110.4 (8)
N10—Cu2—N11—C1716.3 (5)C17—N11—C19—C181.4 (8)
N8—Cu2—N11—C1794.9 (5)Cu2—N11—C19—C18178.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2C···O11i0.902.283.086 (6)150
N2—H2D···O13ii0.902.263.110 (6)157
N3—H3C···O6iii0.902.563.260 (7)136
N3—H3D···O9iv0.902.403.151 (7)141
N4—H4C···O10iv0.902.223.072 (6)157
N4—H4D···O11i0.902.563.193 (7)128
N8—H8B···O7v0.902.333.094 (6)143
N8—H8C···O30.902.443.267 (5)154
N8—H8C···O40.902.473.218 (6)141
N9—H9B···O8vi0.902.233.050 (6)152
N9—H9C···O160.902.503.100 (6)125
N9—H9C···O7v0.902.433.086 (7)130
N10—H10D···O120.902.533.340 (8)150
N10—H10E···O2vii0.902.283.070 (6)146
C3—H3A···O6iii0.972.353.173 (6)142
C3—H3B···O30.972.583.547 (6)172
C6—H6B···O1i0.972.503.237 (6)132
C8—H8A···O13viii0.962.563.360 (8)143
C12—H12A···O120.972.533.426 (8)153
C15—H15B···O14vi0.972.543.511 (6)177
C17—H17A···O2vii0.932.563.318 (7)139
C18—H18A···O3ix0.932.523.377 (7)153
C20—H20B···O2ix0.962.603.385 (7)140
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x+1, y+1, z; (iii) x+1/2, y+1/2, z1/2; (iv) x+3/2, y1/2, z+1/2; (v) x+1/2, y1/2, z+1/2; (vi) x+1/2, y+1/2, z+1/2; (vii) x, y+1, z; (viii) x+1, y, z; (ix) x+1, y, z.
 

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