μ4-Oxo-hexa-μ2-chloro-tetrakis­[(benz­imidazole-κN)copper(II)] ethanol disolvate: a reformulation

Zhang, Y.-Q.; Xu, D.-J.; Su, J.-R.

doi:10.1107/S160053680301420X

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μ₄-Oxo-hexa-μ₂-chloro-tetrakis[(benzimidazole-κN)copper(II)] ethanol disolvate: a reformulation

Y.-Q. Zhang, D.-J. Xu and J.-R. Su

The title compound [Cu₄Cl₆O(C₇H₆N₂)₄]·2C₂H₅OH, consists of the tetranuclear copper(II) complex and uncoordinated ethanol molecules. The structure was reported previously by Tosik, Bukowska-Strzyzewska & Mrozinski [J. Coord. Chem. (1991), 24, 113–120], but only 0.68 ethanol molecules were found in the asymmetric unit. The present redetermination indicates that two ethanol molecules occur in the asymmetric unit. One ethanol molecule is ordered while the other one is disordered, with the hydroxyl group in two alternative sites. Both disordered hydroxyl groups hydrogen bond to the ordered ethanol molecule with O

O separations of 2.845 (16) and 2.67 (2) Å, and O—H

O angles of 156 and 147°, respectively.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680301420X/cm6047sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680301420X/cm6047Isup2.hkl Contains datablock I

CCDC reference: 225677

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.012 Å
H-atom completeness 84%
Disorder in solvent or counterion
R factor = 0.051
wR factor = 0.185
Data-to-parameter ratio = 20.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O3B    ..  O3B      =       2.60 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.99
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent ....... =          3
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      14.00 Perc.
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........        O3A
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........        O3B
PLAT321_ALERT_2_C Check Hybridisation of  C4     in Solvent/Ion ..          ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         12
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      46.00 A   3  
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C2 H6 O
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              C2 O

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C32 H36 Cl6 Cu4 N8 O3
            Atom count from the _atom_site data:  C32 H30 Cl6 Cu4 N8 O3
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    2
           From the CIF: _chemical_formula_sum  C32 H36 Cl6 Cu4 N8 O3
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         64.00     64.00    0.00
           H         72.00     60.00   12.00
           Cl        12.00     12.00    0.00
           Cu         8.00      8.00    0.00
           N         16.00     16.00    0.00
           O          6.00      6.00    0.00

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  13 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top

Crystal data top

[Cu₄Cl₆O(C₇H₆N₂)₄]·2C₂H₆O	Z = 2
M_r = 1047.55	F(000) = 1052
Triclinic, P1	D_x = 1.681 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 13.0005 (14) Å	Cell parameters from 10395 reflections
b = 13.2362 (15) Å	θ = 3.0–26.0°
c = 13.8867 (9) Å	µ = 2.46 mm⁻¹
α = 68.062 (2)°	T = 298 K
β = 74.315 (2)°	Prism, brown
γ = 71.376 (2)°	0.41 × 0.21 × 0.11 mm
V = 2069.2 (4) Å³

Data collection top

Rigaku R-AXIS-RAPID diffractometer	9365 independent reflections
Radiation source: fine-focus sealed tube	6936 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 10 pixels mm^-1	θ_max = 27.5°, θ_min = 1.6°
ω scans	h = −16→16
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −17→17
T_min = 0.358, T_max = 0.758	l = −18→16
19494 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.185	H-atom parameters constrained
S = 0.86	w = 1/[σ²(F_o²) + (0.1372P)² + 6.2288P] where P = (F_o² + 2F_c²)/3
9365 reflections	(Δ/σ)_max = 0.002
467 parameters	Δρ_max = 1.01 e Å⁻³
0 restraints	Δρ_min = −0.89 e Å⁻³

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cu1	0.75807 (5)	0.50585 (5)	0.64644 (5)	0.03174 (17)
Cu2	0.74675 (5)	0.69365 (6)	0.73823 (5)	0.03392 (17)
Cu3	0.53623 (5)	0.61141 (5)	0.76790 (5)	0.03144 (17)
Cu4	0.63348 (5)	0.75334 (5)	0.54546 (5)	0.03125 (17)
Cl1	0.87940 (11)	0.51696 (12)	0.75346 (12)	0.0406 (3)
Cl2	0.57315 (11)	0.71437 (12)	0.86363 (11)	0.0396 (3)
Cl3	0.44876 (11)	0.74534 (12)	0.61976 (12)	0.0425 (3)
Cl4	0.76734 (12)	0.61371 (12)	0.46720 (11)	0.0415 (3)
Cl5	0.62401 (12)	0.41956 (11)	0.78258 (12)	0.0429 (3)
Cl6	0.74596 (12)	0.85082 (12)	0.57431 (12)	0.0418 (3)
O1	0.6689 (3)	0.6404 (3)	0.6748 (3)	0.0275 (7)
C12	0.9651 (5)	0.3601 (5)	0.5915 (5)	0.0421 (13)
H12	0.9992	0.4147	0.5852	0.050*
C14	0.7439 (6)	0.2379 (6)	0.6345 (6)	0.0534 (17)
H14	0.6752	0.2851	0.6482	0.064*
C15	0.7539 (7)	0.1318 (7)	0.6315 (7)	0.068 (2)
H15	0.6907	0.1073	0.6428	0.082*
C16	0.8590 (7)	0.0596 (6)	0.6115 (7)	0.065 (2)
H16	0.8638	−0.0124	0.6126	0.078*
C17	0.9526 (6)	0.0941 (5)	0.5909 (6)	0.0547 (17)
H17	1.0213	0.0478	0.5756	0.066*
C18	0.9428 (5)	0.1998 (5)	0.5932 (5)	0.0399 (12)
C19	0.8396 (5)	0.2711 (5)	0.6165 (5)	0.0385 (12)
C22	0.7898 (6)	0.7693 (6)	0.8941 (6)	0.0506 (15)
H22	0.7204	0.7655	0.9345	0.061*
C24	1.0100 (5)	0.7440 (6)	0.6832 (5)	0.0490 (15)
H24	0.9941	0.7216	0.6340	0.059*
C25	1.1107 (6)	0.7638 (7)	0.6716 (7)	0.0621 (19)
H25	1.1640	0.7541	0.6136	0.074*
C26	1.1355 (6)	0.7982 (7)	0.7451 (7)	0.067 (2)
H26	1.2043	0.8120	0.7339	0.080*
C27	1.0610 (6)	0.8117 (7)	0.8327 (7)	0.0594 (19)
H27	1.0777	0.8328	0.8824	0.071*
C28	0.9588 (5)	0.7925 (5)	0.8437 (5)	0.0449 (14)
C29	0.9328 (5)	0.7587 (5)	0.7707 (5)	0.0389 (12)
C32	0.3671 (5)	0.5911 (5)	0.9580 (5)	0.0412 (13)
H32	0.4046	0.6168	0.9888	0.049*
C34	0.3170 (5)	0.5115 (6)	0.7638 (5)	0.0473 (14)
H34	0.3714	0.5183	0.7040	0.057*
C35	0.2272 (6)	0.4747 (7)	0.7706 (7)	0.0609 (19)
H35	0.2202	0.4569	0.7142	0.073*
C36	0.1446 (6)	0.4631 (7)	0.8627 (7)	0.064 (2)
H36	0.0850	0.4371	0.8655	0.077*
C37	0.1504 (5)	0.4889 (6)	0.9462 (6)	0.0547 (17)
H37	0.0962	0.4819	1.0061	0.066*
C38	0.2419 (5)	0.5265 (5)	0.9376 (5)	0.0401 (12)
C39	0.3239 (4)	0.5381 (5)	0.8484 (4)	0.0344 (11)
C42	0.5865 (5)	0.9787 (5)	0.3924 (4)	0.0394 (12)
H42	0.6021	1.0095	0.4354	0.047*
C44	0.5604 (5)	0.7647 (5)	0.3106 (6)	0.0485 (15)
H44	0.5770	0.6932	0.3588	0.058*
C45	0.5306 (6)	0.7818 (6)	0.2169 (6)	0.0563 (17)
H45	0.5281	0.7204	0.2009	0.068*
C46	0.5040 (7)	0.8895 (8)	0.1452 (6)	0.068 (2)
H46	0.4835	0.8977	0.0830	0.082*
C47	0.5071 (7)	0.9852 (6)	0.1634 (5)	0.0579 (18)
H47	0.4901	1.0566	0.1151	0.069*
C48	0.5373 (5)	0.9670 (5)	0.2581 (5)	0.0430 (13)
C49	0.5646 (4)	0.8587 (5)	0.3303 (4)	0.0353 (11)
N11	1.0190 (4)	0.2614 (4)	0.5760 (4)	0.0430 (11)
H11	1.0892	0.2395	0.5584	0.052*
N13	0.8574 (4)	0.3707 (4)	0.6168 (4)	0.0366 (10)
N21	0.8663 (5)	0.7992 (5)	0.9202 (5)	0.0557 (15)
H21	0.8585	0.8188	0.9747	0.067*
N23	0.8249 (4)	0.7463 (4)	0.8052 (4)	0.0386 (10)
N31	0.2728 (4)	0.5620 (5)	1.0050 (4)	0.0438 (12)
H31	0.2372	0.5648	1.0663	0.053*
N33	0.4022 (4)	0.5800 (4)	0.8644 (4)	0.0347 (10)
N41	0.5527 (4)	1.0385 (4)	0.3009 (4)	0.0456 (12)
H41	0.5422	1.1102	0.2729	0.055*
N43	0.5954 (4)	0.8694 (4)	0.4153 (3)	0.0343 (9)
O2	0.9102 (6)	0.8357 (8)	1.0866 (5)	0.098 (2)
H2	0.9763	0.8383	1.0864	0.100*
C1	0.8484 (9)	0.8217 (10)	1.1896 (7)	0.089 (3)
H1A	0.8823	0.7511	1.2374	0.107*
H1B	0.7743	0.8198	1.1900	0.107*
C2	0.8440 (9)	0.9171 (10)	1.2253 (8)	0.087 (3)
H2A	0.8014	0.9079	1.2949	0.130*
H2B	0.8103	0.9868	1.1777	0.130*
H2C	0.9174	0.9178	1.2260	0.130*
O3a	1.1319 (9)	0.7766 (10)	1.1179 (9)	0.099 (3)*	0.68
O3b	1.0840 (18)	0.9222 (19)	1.0359 (17)	0.086 (6)*	0.32
C3	1.1629 (12)	0.8802 (13)	1.0990 (12)	0.121 (4)*
C4	1.2687 (15)	0.8724 (16)	1.0372 (15)	0.154 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0328 (3)	0.0271 (3)	0.0342 (3)	−0.0063 (2)	−0.0016 (3)	−0.0121 (3)
Cu2	0.0359 (3)	0.0366 (4)	0.0366 (4)	−0.0133 (3)	−0.0076 (3)	−0.0150 (3)
Cu3	0.0291 (3)	0.0320 (3)	0.0322 (3)	−0.0119 (2)	0.0020 (2)	−0.0103 (3)
Cu4	0.0321 (3)	0.0298 (3)	0.0289 (3)	−0.0096 (2)	−0.0040 (3)	−0.0051 (3)
Cl1	0.0354 (6)	0.0428 (7)	0.0502 (8)	−0.0054 (5)	−0.0134 (6)	−0.0212 (6)
Cl2	0.0395 (7)	0.0474 (8)	0.0393 (7)	−0.0161 (6)	0.0007 (6)	−0.0222 (6)
Cl3	0.0302 (6)	0.0455 (8)	0.0432 (8)	−0.0119 (5)	−0.0073 (6)	−0.0015 (6)
Cl4	0.0455 (7)	0.0422 (7)	0.0310 (6)	−0.0019 (6)	−0.0036 (6)	−0.0145 (6)
Cl5	0.0447 (7)	0.0307 (6)	0.0491 (8)	−0.0160 (5)	0.0088 (6)	−0.0141 (6)
Cl6	0.0510 (8)	0.0360 (7)	0.0441 (8)	−0.0224 (6)	−0.0128 (6)	−0.0059 (6)
O1	0.0292 (16)	0.0253 (16)	0.0281 (17)	−0.0101 (13)	−0.0016 (14)	−0.0079 (14)
C12	0.040 (3)	0.038 (3)	0.049 (3)	−0.010 (2)	−0.001 (3)	−0.019 (3)
C14	0.046 (3)	0.057 (4)	0.069 (5)	−0.016 (3)	0.001 (3)	−0.037 (4)
C15	0.070 (5)	0.065 (5)	0.088 (6)	−0.030 (4)	0.001 (4)	−0.044 (5)
C16	0.081 (5)	0.043 (4)	0.081 (5)	−0.023 (4)	−0.002 (4)	−0.032 (4)
C17	0.068 (4)	0.036 (3)	0.061 (4)	−0.004 (3)	−0.006 (3)	−0.028 (3)
C18	0.046 (3)	0.035 (3)	0.036 (3)	−0.005 (2)	−0.005 (2)	−0.014 (2)
C19	0.039 (3)	0.038 (3)	0.042 (3)	−0.007 (2)	−0.001 (2)	−0.022 (3)
C22	0.052 (3)	0.062 (4)	0.051 (4)	−0.021 (3)	−0.006 (3)	−0.028 (3)
C24	0.047 (3)	0.057 (4)	0.045 (3)	−0.017 (3)	−0.007 (3)	−0.016 (3)
C25	0.046 (4)	0.067 (5)	0.069 (5)	−0.017 (3)	0.001 (3)	−0.021 (4)
C26	0.050 (4)	0.068 (5)	0.091 (6)	−0.025 (4)	−0.020 (4)	−0.021 (4)
C27	0.060 (4)	0.064 (4)	0.074 (5)	−0.025 (4)	−0.025 (4)	−0.026 (4)
C28	0.053 (3)	0.042 (3)	0.048 (3)	−0.019 (3)	−0.012 (3)	−0.016 (3)
C29	0.041 (3)	0.035 (3)	0.045 (3)	−0.011 (2)	−0.016 (3)	−0.010 (2)
C32	0.039 (3)	0.045 (3)	0.039 (3)	−0.012 (2)	0.000 (2)	−0.016 (3)
C34	0.043 (3)	0.053 (4)	0.048 (4)	−0.016 (3)	0.000 (3)	−0.020 (3)
C35	0.062 (4)	0.067 (5)	0.070 (5)	−0.015 (4)	−0.016 (4)	−0.037 (4)
C36	0.041 (3)	0.078 (5)	0.085 (6)	−0.028 (3)	−0.010 (4)	−0.028 (4)
C37	0.035 (3)	0.063 (4)	0.061 (4)	−0.020 (3)	0.001 (3)	−0.014 (3)
C38	0.033 (3)	0.039 (3)	0.046 (3)	−0.012 (2)	−0.004 (2)	−0.010 (3)
C39	0.028 (2)	0.032 (3)	0.037 (3)	−0.008 (2)	−0.001 (2)	−0.007 (2)
C42	0.044 (3)	0.034 (3)	0.033 (3)	−0.008 (2)	−0.001 (2)	−0.009 (2)
C44	0.049 (3)	0.037 (3)	0.060 (4)	−0.013 (3)	−0.018 (3)	−0.009 (3)
C45	0.065 (4)	0.058 (4)	0.061 (4)	−0.024 (3)	−0.021 (4)	−0.019 (3)
C46	0.080 (5)	0.081 (6)	0.047 (4)	−0.021 (4)	−0.026 (4)	−0.013 (4)
C47	0.075 (5)	0.048 (4)	0.044 (4)	−0.011 (3)	−0.027 (4)	0.001 (3)
C48	0.042 (3)	0.039 (3)	0.042 (3)	−0.008 (2)	−0.009 (3)	−0.008 (3)
C49	0.028 (2)	0.038 (3)	0.034 (3)	−0.009 (2)	−0.006 (2)	−0.004 (2)
N11	0.032 (2)	0.042 (3)	0.053 (3)	−0.005 (2)	0.001 (2)	−0.023 (2)
N13	0.034 (2)	0.031 (2)	0.045 (3)	−0.0065 (18)	−0.002 (2)	−0.017 (2)
N21	0.062 (3)	0.069 (4)	0.057 (3)	−0.025 (3)	−0.008 (3)	−0.036 (3)
N23	0.042 (2)	0.042 (3)	0.042 (3)	−0.014 (2)	−0.010 (2)	−0.018 (2)
N31	0.037 (2)	0.056 (3)	0.034 (3)	−0.015 (2)	0.008 (2)	−0.016 (2)
N33	0.034 (2)	0.034 (2)	0.035 (2)	−0.0127 (18)	0.0024 (19)	−0.0115 (19)
N41	0.057 (3)	0.029 (2)	0.038 (3)	−0.005 (2)	−0.007 (2)	−0.003 (2)
N43	0.032 (2)	0.037 (2)	0.030 (2)	−0.0082 (18)	−0.0039 (18)	−0.0060 (19)
O2	0.091 (5)	0.169 (8)	0.064 (4)	−0.052 (5)	−0.002 (3)	−0.060 (5)
C1	0.089 (7)	0.135 (9)	0.053 (5)	−0.052 (7)	0.004 (5)	−0.029 (6)
C2	0.083 (6)	0.108 (8)	0.074 (6)	−0.020 (6)	−0.011 (5)	−0.039 (6)

Geometric parameters (Å, º) top

Cu1—O1	1.905 (3)	C28—C29	1.401 (8)
Cu1—N13	1.955 (4)	C29—N23	1.396 (8)
Cu1—Cl4	2.3538 (15)	C32—N31	1.327 (8)
Cu1—Cl5	2.4068 (15)	C32—N33	1.302 (7)
Cu1—Cl1	2.5095 (14)	C32—H32	0.93
Cu2—O1	1.923 (3)	C34—C35	1.370 (10)
Cu2—N23	1.957 (4)	C34—C39	1.379 (8)
Cu2—Cl1	2.3958 (15)	C34—H34	0.93
Cu2—Cl6	2.4435 (16)	C35—C36	1.425 (11)
Cu2—Cl2	2.4571 (15)	C35—H35	0.93
Cu3—O1	1.908 (3)	C36—C37	1.351 (11)
Cu3—N33	1.947 (4)	C36—H36	0.93
Cu3—Cl5	2.3833 (15)	C37—C38	1.390 (8)
Cu3—Cl3	2.4331 (15)	C37—H37	0.93
Cu3—Cl2	2.4436 (15)	C38—C39	1.394 (8)
Cu4—O1	1.916 (3)	C38—N31	1.383 (8)
Cu4—N43	1.948 (4)	C39—N33	1.402 (7)
Cu4—Cl3	2.3629 (15)	C42—N41	1.327 (7)
Cu4—Cl6	2.4231 (14)	C42—N43	1.333 (7)
Cu4—Cl4	2.4596 (15)	C42—H42	0.93
C12—N13	1.322 (7)	C44—C45	1.375 (9)
C12—N11	1.336 (8)	C44—C49	1.390 (8)
C12—H12	0.93	C44—H44	0.93
C14—C19	1.379 (9)	C45—C46	1.398 (11)
C14—C15	1.385 (10)	C45—H45	0.93
C14—H14	0.93	C46—C47	1.395 (11)
C15—C16	1.420 (11)	C46—H46	0.93
C15—H15	0.93	C47—C48	1.386 (9)
C16—C17	1.357 (11)	C47—H47	0.93
C16—H16	0.93	C48—N41	1.378 (8)
C17—C18	1.375 (8)	C48—C49	1.407 (8)
C17—H17	0.93	C49—N43	1.411 (7)
C18—N11	1.395 (8)	N11—H11	0.86
C18—C19	1.408 (8)	N21—H21	0.86
C19—N13	1.411 (7)	N31—H31	0.86
C22—N23	1.308 (8)	N41—H41	0.86
C22—N21	1.354 (8)	O2—C1	1.415 (10)
C22—H22	0.93	O2—H2	0.869
C24—C25	1.373 (10)	C1—C2	1.501 (14)
C24—C29	1.383 (9)	C1—H1A	0.97
C24—H24	0.93	C1—H1B	0.97
C25—C26	1.404 (11)	C2—H2A	0.96
C25—H25	0.93	C2—H2B	0.96
C26—C27	1.366 (12)	C2—H2C	0.96
C26—H26	0.93	O3a—C3	1.462 (17)
C27—C28	1.389 (9)	O3b—C3	1.37 (2)
C27—H27	0.93	C3—C4	1.41 (2)
C28—N21	1.377 (9)

O1—Cu1—N13	176.53 (17)	C27—C28—N21	131.6 (6)
O1—Cu1—Cl4	86.03 (11)	C27—C28—C29	122.6 (6)
N13—Cu1—Cl4	93.65 (15)	N21—C28—C29	105.9 (5)
O1—Cu1—Cl5	84.07 (11)	C24—C29—C28	120.0 (6)
N13—Cu1—Cl5	98.50 (15)	C24—C29—N23	132.1 (5)
Cl4—Cu1—Cl5	136.07 (6)	C28—C29—N23	107.9 (5)
O1—Cu1—Cl1	83.11 (10)	N31—C32—N33	113.4 (5)
N13—Cu1—Cl1	94.07 (14)	N31—C32—H32	123.3
Cl4—Cu1—Cl1	119.75 (6)	N33—C32—H32	123.3
Cl5—Cu1—Cl1	101.35 (6)	C35—C34—C39	117.8 (6)
O1—Cu2—N23	179.00 (19)	C35—C34—H34	121.1
O1—Cu2—Cl1	85.91 (11)	C39—C34—H34	121.1
N23—Cu2—Cl1	93.93 (15)	C34—C35—C36	120.9 (6)
O1—Cu2—Cl6	84.86 (11)	C34—C35—H35	119.5
N23—Cu2—Cl6	96.05 (15)	C36—C35—H35	119.5
Cl1—Cu2—Cl6	122.20 (6)	C37—C36—C35	121.8 (6)
O1—Cu2—Cl2	84.07 (11)	C37—C36—H36	119.1
N23—Cu2—Cl2	95.20 (15)	C35—C36—H36	119.1
Cl1—Cu2—Cl2	122.30 (6)	C36—C37—C38	116.4 (6)
Cl6—Cu2—Cl2	113.21 (6)	C36—C37—H37	121.8
O1—Cu3—N33	179.15 (19)	C38—C37—H37	121.8
O1—Cu3—Cl5	84.67 (11)	C39—C38—C37	122.8 (6)
N33—Cu3—Cl5	94.76 (14)	C39—C38—N31	105.2 (5)
O1—Cu3—Cl3	83.77 (11)	C37—C38—N31	131.9 (6)
N33—Cu3—Cl3	97.08 (14)	C34—C39—N33	131.5 (5)
Cl5—Cu3—Cl3	124.22 (6)	C34—C39—C38	120.2 (5)
O1—Cu3—Cl2	84.75 (11)	N33—C39—C38	108.3 (5)
N33—Cu3—Cl2	95.05 (14)	N41—C42—N43	112.1 (5)
Cl5—Cu3—Cl2	123.98 (6)	N41—C42—H42	123.9
Cl3—Cu3—Cl2	108.95 (6)	N43—C42—H42	123.9
O1—Cu4—N43	179.06 (17)	C45—C44—C49	117.3 (6)
O1—Cu4—Cl3	85.55 (11)	C45—C44—H44	121.4
N43—Cu4—Cl3	93.77 (14)	C49—C44—H44	121.4
O1—Cu4—Cl6	85.58 (10)	C44—C45—C46	121.3 (7)
N43—Cu4—Cl6	94.37 (14)	C44—C45—H45	119.3
Cl3—Cu4—Cl6	129.53 (6)	C46—C45—H45	119.3
O1—Cu4—Cl4	82.86 (11)	C47—C46—C45	122.5 (7)
N43—Cu4—Cl4	98.05 (14)	C47—C46—H46	118.8
Cl3—Cu4—Cl4	123.70 (6)	C45—C46—H46	118.8
Cl6—Cu4—Cl4	104.21 (6)	C46—C47—C48	115.7 (6)
Cu2—Cl1—Cu1	79.56 (4)	C46—C47—H47	122.2
Cu3—Cl2—Cu2	79.42 (4)	C48—C47—H47	122.2
Cu4—Cl3—Cu3	81.17 (5)	N41—C48—C49	105.7 (5)
Cu1—Cl4—Cu4	80.74 (5)	N41—C48—C47	132.1 (6)
Cu3—Cl5—Cu1	80.97 (5)	C49—C48—C47	122.1 (6)
Cu4—Cl6—Cu2	79.91 (4)	C44—C49—C48	121.1 (5)
Cu1—O1—Cu3	109.28 (16)	C44—C49—N43	131.3 (5)
Cu1—O1—Cu4	109.40 (17)	C48—C49—N43	107.6 (5)
Cu3—O1—Cu4	109.38 (16)	C12—N11—C18	108.8 (5)
Cu1—O1—Cu2	110.18 (16)	C12—N11—H11	125.6
Cu3—O1—Cu2	109.62 (17)	C18—N11—H11	125.6
Cu4—O1—Cu2	108.97 (16)	C12—N13—C19	106.2 (5)
N13—C12—N11	112.0 (5)	C12—N13—Cu1	120.9 (4)
N13—C12—H12	124.0	C19—N13—Cu1	132.9 (4)
N11—C12—H12	124.0	C22—N21—C28	107.6 (5)
C19—C14—C15	117.6 (7)	C22—N21—H21	126.2
C19—C14—H14	121.2	C28—N21—H21	126.2
C15—C14—H14	121.2	C22—N23—C29	106.6 (5)
C14—C15—C16	121.0 (7)	C22—N23—Cu2	127.1 (4)
C14—C15—H15	119.5	C29—N23—Cu2	126.1 (4)
C16—C15—H15	119.5	C32—N31—C38	107.6 (5)
C17—C16—C15	121.0 (6)	C32—N31—H31	126.2
C17—C16—H16	119.5	C38—N31—H31	126.2
C15—C16—H16	119.5	C32—N33—C39	105.4 (5)
C18—C17—C16	118.0 (6)	C32—N33—Cu3	127.6 (4)
C18—C17—H17	121.0	C39—N33—Cu3	127.0 (4)
C16—C17—H17	121.0	C42—N41—C48	108.8 (5)
C17—C18—N11	133.4 (6)	C42—N41—H41	125.6
C17—C18—C19	121.9 (6)	C48—N41—H41	125.6
N11—C18—C19	104.7 (5)	C42—N43—C49	105.8 (4)
C14—C19—N13	131.4 (5)	C42—N43—Cu4	125.6 (4)
C14—C19—C18	120.5 (6)	C49—N43—Cu4	128.5 (4)
N13—C19—C18	108.2 (5)	C1—O2—H2	109.4
N23—C22—N21	112.0 (6)	O2—C1—C2	109.6 (9)
N23—C22—H22	124.0	O2—C1—H1A	109.8
N21—C22—H22	124.0	C2—C1—H1A	109.8
C25—C24—C29	117.7 (6)	O2—C1—H1B	109.8
C25—C24—H24	121.2	C2—C1—H1B	109.8
C29—C24—H24	121.2	H1A—C1—H1B	108.2
C24—C25—C26	121.7 (7)	C1—C2—H2A	109.5
C24—C25—H25	119.1	C1—C2—H2B	109.5
C26—C25—H25	119.1	H2A—C2—H2B	109.5
C27—C26—C25	121.5 (7)	C1—C2—H2C	109.5
C27—C26—H26	119.2	H2A—C2—H2C	109.5
C25—C26—H26	119.2	H2B—C2—H2C	109.5
C26—C27—C28	116.5 (6)	O3b—C3—C4	110.3 (16)
C26—C27—H27	121.7	O3a—C3—C4	107.1 (13)
C28—C27—H27	121.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3a	0.87	2.03	2.845 (16)	156
O2—H2···O3b	0.87	1.88	2.67 (2)	147
N11—H11···Cl6ⁱ	0.86	2.70	3.445 (6)	146
N21—H21···O2	0.86	1.96	2.761 (10)	155
N31—H31···Cl1ⁱⁱ	0.86	2.59	3.372 (5)	152
N41—H41···Cl2ⁱⁱⁱ	0.86	2.69	3.408 (5)	141

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+2; (iii) −x+1, −y+2, −z+1.

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