Di-μ-chloro-bis­[(2,2′:6,2′′-ter­pyridine-κ3N)copper(II)] diperchlorate: the triclinic polymorph

Gasser, G.; Labat, G.; Stoeckli-Evans, H.

doi:10.1107/S1600536804000443

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Di-μ-chloro-bis[(2,2′:6,2′′-terpyridine-κ³N)copper(II)] diperchlorate: the triclinic polymorph

G. Gasser, G. Labat and H. Stoeckli-Evans

The title compound, [Cu₂Cl₂(C₁₅H₁₁N₃)₂](ClO₄)₂, crystallized from water as the triclinic polymorph. There are two independent centrosymmetric binuclear dications, [Cu₂(terpyridine)₂Cl₂]²⁺, and four perchlorate anions per unit cell. Each Cu atom has a distorted square-pyramidal geometry. In the crystal structure, the cations are bridged by the perchlorate anions via C—H

O hydrogen bonds, thereby forming a three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804000443/fl6078sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804000443/fl6078Isup2.hkl Contains datablock I

CCDC reference: 234832

checkCIF report

Key indicators

Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.015 Å
R factor = 0.068
wR factor = 0.185
Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.93

Author Response: ...With the Stoe Image Plate diffraction System Mark I it is only possible to access a maximum of ca. 93% of the Ewald sphere in the triclinic system, if maximum atomic resolution, 0.81 \%A, is to be obtained. Here Theta max. was 25.96\%.


Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.250     0.917
            Tmin' and Tmax expected:      0.420     0.917
            RR' =      0.595
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.59

Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           25.96
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               5819
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         6260
           Completeness (_total/calc)             92.96%
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.100
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.93
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         43 Perc.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....       Cl10
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....       Cl20
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         15
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         15
            CL1 -CU1 -N2  -C6    -79.00 11.00   2.776   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         19
            CL1 -CU1 -N2  -C10   103.00 11.00   2.776   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         73
            N22 -CU2 -CL2 -CU2  -179.00100.00   1.555   1.555   1.555   2.665
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         87
            CL2 -CU2 -N22 -C30   -95.00 12.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         91
            CL2 -CU2 -N22 -C26    84.00 12.00   1.555   1.555   1.555   1.555

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

   1 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
   8 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: EXPOSE (Stoe & Cie, 2000); cell refinement: CELL (Stoe & Cie, 2000); data reduction: INTEGRATE (Stoe & Cie, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON99 (Spek, 1990); software used to prepare material for publication: SHELXL97.

Di-µ-chloro-bis[(2,2':6,2"-terpyridine-κ³N)copper(II)] diperchlorate top

Crystal data top

[Cu₂Cl₂(C₁₅H₁₁N₃)₂](ClO₄)₂	Z = 2
M_r = 863.42	F(000) = 868
Triclinic, P1	D_x = 1.796 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9905 (8) Å	Cell parameters from 6421 reflections
b = 9.8696 (11) Å	θ = 2.2–25.8°
c = 23.782 (2) Å	µ = 1.73 mm⁻¹
α = 91.431 (13)°	T = 153 K
β = 93.524 (13)°	Needle, pale_blue
γ = 102.678 (14)°	0.50 × 0.05 × 0.05 mm
V = 1596.6 (3) Å³

Data collection top

Stoe IPDS diffractometer	5819 independent reflections
Radiation source: fine-focus sealed tube	2512 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.100
Detector resolution: 0.81Å pixels mm^-1	θ_max = 26.0°, θ_min = 2.1°
φ oscillation scans	h = −8→8
Absorption correction: part of the refinement model (ΔF) (DIFABS in PLATON; Spek, 1990)	k = −12→12
T_min = 0.250, T_max = 0.917	l = −29→29
12643 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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.185	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0663P)²] where P = (F_o² + 2F_c²)/3
5819 reflections	(Δ/σ)_max < 0.001
451 parameters	Δρ_max = 0.65 e Å⁻³
0 restraints	Δρ_min = −0.70 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
Cu1	0.97707 (17)	0.86803 (13)	0.44552 (5)	0.0361 (3)
Cl1	0.8358 (4)	1.0976 (3)	0.47442 (10)	0.0380 (6)
N1	1.1757 (12)	0.9567 (8)	0.3908 (3)	0.035 (2)
N2	0.8173 (12)	0.8343 (8)	0.3752 (4)	0.036 (2)
N3	0.7314 (11)	0.7503 (8)	0.4741 (4)	0.037 (2)
C1	1.3672 (15)	1.0212 (10)	0.4023 (5)	0.039 (3)
H1A	1.4229	1.0219	0.4398	0.047*
C2	1.4814 (15)	1.0839 (10)	0.3628 (5)	0.041 (3)
H2A	1.6143	1.1290	0.3727	0.049*
C3	1.4060 (15)	1.0826 (11)	0.3084 (5)	0.040 (3)
H3A	1.4870	1.1259	0.2803	0.048*
C4	1.2141 (16)	1.0193 (11)	0.2942 (5)	0.044 (3)
H4A	1.1604	1.0192	0.2565	0.053*
C5	1.0978 (14)	0.9545 (10)	0.3361 (4)	0.035 (2)
C6	0.8912 (14)	0.8826 (9)	0.3277 (4)	0.035 (2)
C7	0.7778 (15)	0.8609 (11)	0.2773 (4)	0.043 (3)
H7A	0.8307	0.8934	0.2430	0.052*
C8	0.5824 (16)	0.7895 (11)	0.2787 (5)	0.048 (3)
H8A	0.4988	0.7768	0.2451	0.057*
C9	0.5100 (15)	0.7379 (11)	0.3273 (4)	0.045 (3)
H9A	0.3792	0.6845	0.3274	0.054*
C10	0.6299 (16)	0.7643 (10)	0.3767 (5)	0.044 (3)
C11	0.5742 (16)	0.7194 (10)	0.4334 (4)	0.040 (3)
C12	0.3909 (16)	0.6603 (9)	0.4475 (5)	0.042 (3)
H12A	0.2864	0.6406	0.4190	0.051*
C13	0.3525 (18)	0.6282 (11)	0.5017 (5)	0.049 (3)
H13A	0.2224	0.5921	0.5120	0.059*
C14	0.5111 (18)	0.6504 (11)	0.5411 (5)	0.051 (3)
H14A	0.4919	0.6229	0.5787	0.061*
C15	0.6957 (16)	0.7119 (10)	0.5264 (4)	0.040 (3)
H15A	0.8018	0.7276	0.5545	0.048*
Cu2	0.49588 (17)	0.37471 (13)	0.05317 (5)	0.0341 (3)
Cl2	0.6445 (3)	0.3942 (3)	−0.02731 (10)	0.0367 (6)
N21	0.7200 (11)	0.4704 (8)	0.1078 (3)	0.0329 (19)
N22	0.3683 (11)	0.3544 (8)	0.1238 (3)	0.0310 (18)
N23	0.2343 (12)	0.2518 (8)	0.0244 (4)	0.038 (2)
C21	0.9068 (14)	0.5336 (10)	0.0950 (4)	0.038 (2)
H21A	0.9434	0.5277	0.0573	0.046*
C22	1.0425 (14)	0.6059 (10)	0.1361 (4)	0.038 (2)
H22A	1.1716	0.6474	0.1265	0.045*
C23	0.9930 (14)	0.6179 (10)	0.1901 (4)	0.041 (3)
H23A	1.0843	0.6709	0.2179	0.049*
C24	0.8081 (14)	0.5518 (11)	0.2037 (4)	0.038 (2)
H24A	0.7717	0.5555	0.2415	0.046*
C25	0.6763 (14)	0.4803 (10)	0.1621 (4)	0.035 (2)
C26	0.4722 (14)	0.4097 (10)	0.1715 (4)	0.032 (2)
C27	0.3854 (15)	0.3956 (11)	0.2222 (4)	0.042 (3)
H27A	0.4565	0.4326	0.2566	0.050*
C28	0.1875 (14)	0.3241 (10)	0.2211 (4)	0.038 (2)
H28A	0.1217	0.3155	0.2551	0.046*
C29	0.0898 (15)	0.2677 (10)	0.1724 (4)	0.042 (3)
H29A	−0.0429	0.2176	0.1722	0.050*
C30	0.1844 (14)	0.2835 (10)	0.1224 (4)	0.036 (2)
C31	0.0941 (15)	0.2304 (10)	0.0647 (4)	0.037 (2)
C32	−0.0865 (16)	0.1705 (10)	0.0515 (5)	0.041 (3)
H32A	−0.1760	0.1566	0.0804	0.049*
C33	−0.1554 (17)	0.1258 (11)	−0.0028 (5)	0.048 (3)
H33A	−0.2908	0.0874	−0.0122	0.057*
C34	−0.0156 (15)	0.1398 (11)	−0.0436 (5)	0.044 (3)
H34A	−0.0517	0.1045	−0.0812	0.053*
C35	0.1755 (13)	0.2062 (9)	−0.0274 (4)	0.029 (2)
H35A	0.2692	0.2195	−0.0552	0.035*
Cl10	0.9262 (4)	0.4730 (3)	0.35570 (11)	0.0504 (7)
O11	1.0406 (11)	0.5774 (10)	0.3218 (3)	0.074 (3)
O12	0.9430 (12)	0.5248 (11)	0.4128 (3)	0.080 (3)
O13	1.002 (2)	0.3543 (13)	0.3544 (5)	0.133 (5)
O14	0.7269 (11)	0.4450 (10)	0.3349 (4)	0.078 (3)
Cl20	0.5037 (4)	0.0020 (3)	0.14758 (11)	0.0441 (7)
O21	0.4745 (10)	0.0541 (8)	0.0929 (3)	0.056 (2)
O22	0.6068 (11)	0.1136 (9)	0.1853 (3)	0.060 (2)
O23	0.3236 (11)	−0.0567 (10)	0.1695 (4)	0.074 (3)
O24	0.6249 (16)	−0.0966 (11)	0.1436 (4)	0.091 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0360 (7)	0.0374 (7)	0.0337 (7)	0.0052 (6)	0.0034 (5)	0.0004 (6)
Cl1	0.0413 (14)	0.0412 (15)	0.0325 (14)	0.0120 (11)	0.0004 (10)	0.0023 (12)
N1	0.041 (5)	0.036 (5)	0.030 (5)	0.012 (4)	0.002 (4)	−0.007 (4)
N2	0.040 (5)	0.025 (4)	0.040 (5)	0.002 (4)	0.005 (4)	0.000 (4)
N3	0.040 (5)	0.023 (4)	0.046 (6)	0.000 (4)	0.010 (4)	−0.006 (4)
C1	0.039 (6)	0.030 (6)	0.050 (7)	0.011 (5)	0.006 (5)	0.010 (5)
C2	0.034 (6)	0.036 (6)	0.054 (7)	0.009 (5)	0.011 (5)	−0.001 (6)
C3	0.041 (7)	0.037 (6)	0.044 (7)	0.009 (5)	0.015 (5)	0.005 (5)
C4	0.057 (7)	0.042 (6)	0.037 (6)	0.015 (5)	0.007 (5)	0.009 (6)
C5	0.035 (6)	0.040 (6)	0.031 (6)	0.012 (5)	0.004 (4)	−0.003 (5)
C6	0.046 (6)	0.022 (5)	0.036 (6)	0.010 (4)	−0.001 (5)	−0.007 (5)
C7	0.051 (7)	0.045 (7)	0.035 (6)	0.015 (5)	0.003 (5)	−0.006 (5)
C8	0.047 (7)	0.049 (7)	0.044 (7)	0.006 (5)	0.003 (5)	0.001 (6)
C9	0.042 (6)	0.050 (7)	0.040 (7)	0.006 (5)	−0.015 (5)	−0.019 (6)
C10	0.051 (7)	0.027 (6)	0.057 (7)	0.013 (5)	0.005 (5)	−0.005 (6)
C11	0.057 (7)	0.024 (5)	0.036 (6)	0.008 (5)	−0.001 (5)	−0.006 (5)
C12	0.051 (7)	0.018 (5)	0.052 (7)	−0.004 (5)	0.001 (5)	−0.004 (5)
C13	0.056 (8)	0.032 (6)	0.065 (8)	0.012 (5)	0.033 (7)	0.011 (6)
C14	0.061 (8)	0.043 (7)	0.053 (7)	0.017 (6)	0.023 (6)	0.005 (6)
C15	0.056 (7)	0.039 (6)	0.029 (6)	0.018 (5)	0.006 (5)	−0.001 (5)
Cu2	0.0325 (7)	0.0359 (7)	0.0324 (7)	0.0041 (5)	0.0026 (5)	−0.0005 (6)
Cl2	0.0351 (14)	0.0425 (14)	0.0339 (14)	0.0112 (11)	0.0054 (10)	−0.0005 (12)
N21	0.031 (5)	0.039 (5)	0.029 (5)	0.009 (4)	0.004 (3)	0.005 (4)
N22	0.033 (5)	0.026 (4)	0.035 (5)	0.008 (4)	0.004 (4)	0.009 (4)
N23	0.040 (5)	0.023 (4)	0.051 (6)	0.009 (4)	0.005 (4)	0.004 (4)
C21	0.040 (6)	0.032 (6)	0.045 (6)	0.013 (5)	0.004 (5)	−0.002 (5)
C22	0.037 (6)	0.035 (6)	0.040 (6)	0.006 (5)	−0.001 (5)	0.010 (5)
C23	0.034 (6)	0.036 (6)	0.047 (7)	−0.001 (5)	−0.002 (5)	−0.003 (5)
C24	0.036 (6)	0.050 (7)	0.030 (5)	0.009 (5)	0.011 (4)	0.005 (5)
C25	0.034 (6)	0.034 (6)	0.036 (6)	0.008 (4)	0.000 (4)	−0.003 (5)
C26	0.038 (6)	0.029 (5)	0.030 (6)	0.010 (4)	0.003 (4)	0.001 (5)
C27	0.045 (7)	0.042 (6)	0.038 (6)	0.007 (5)	0.004 (5)	0.004 (5)
C28	0.043 (6)	0.035 (6)	0.037 (6)	0.009 (5)	0.014 (5)	0.002 (5)
C29	0.045 (6)	0.038 (6)	0.040 (6)	0.001 (5)	0.013 (5)	0.008 (5)
C30	0.028 (6)	0.032 (6)	0.051 (7)	0.009 (4)	0.006 (5)	−0.001 (5)
C31	0.044 (7)	0.034 (6)	0.037 (6)	0.014 (5)	0.009 (5)	0.012 (5)
C32	0.043 (7)	0.031 (6)	0.049 (7)	0.004 (5)	0.008 (5)	−0.001 (5)
C33	0.050 (7)	0.034 (6)	0.060 (8)	0.013 (5)	−0.010 (6)	0.003 (6)
C34	0.042 (7)	0.036 (6)	0.053 (7)	0.011 (5)	−0.006 (5)	−0.010 (6)
C35	0.037 (6)	0.026 (5)	0.023 (5)	0.007 (4)	−0.007 (4)	−0.005 (4)
Cl10	0.0436 (16)	0.068 (2)	0.0391 (15)	0.0089 (14)	0.0048 (12)	0.0082 (15)
O11	0.048 (5)	0.109 (7)	0.049 (5)	−0.019 (5)	0.001 (4)	0.017 (5)
O12	0.063 (6)	0.119 (8)	0.046 (5)	−0.005 (5)	0.009 (4)	−0.006 (5)
O13	0.203 (14)	0.135 (11)	0.106 (9)	0.118 (11)	0.050 (9)	0.037 (8)
O14	0.037 (5)	0.116 (8)	0.064 (6)	−0.016 (5)	−0.008 (4)	0.030 (6)
Cl20	0.0389 (15)	0.0543 (17)	0.0359 (15)	0.0036 (12)	0.0034 (11)	−0.0012 (14)
O21	0.049 (5)	0.063 (5)	0.046 (5)	−0.006 (4)	−0.017 (4)	0.011 (4)
O22	0.059 (5)	0.070 (6)	0.036 (4)	−0.015 (4)	0.008 (4)	−0.006 (4)
O23	0.042 (5)	0.103 (7)	0.063 (6)	−0.016 (5)	0.013 (4)	−0.010 (5)
O24	0.137 (9)	0.102 (8)	0.059 (6)	0.080 (7)	0.017 (6)	0.012 (6)

Geometric parameters (Å, º) top

Cu1—N2	1.932 (8)	Cu2—Cl2ⁱⁱ	2.743 (3)
Cu1—N3	2.017 (8)	Cl2—Cu2ⁱⁱ	2.743 (3)
Cu1—N1	2.033 (8)	N21—C25	1.350 (12)
Cu1—Cl1ⁱ	2.218 (3)	N21—C21	1.374 (12)
Cu1—Cl1	2.751 (3)	N22—C30	1.320 (12)
Cl1—Cu1ⁱ	2.218 (3)	N22—C26	1.345 (11)
N1—C1	1.358 (12)	N23—C35	1.311 (11)
N1—C5	1.378 (12)	N23—C31	1.400 (12)
N2—C6	1.327 (12)	C21—C22	1.385 (13)
N2—C10	1.343 (13)	C21—H21A	0.9500
N3—C15	1.332 (12)	C22—C23	1.360 (14)
N3—C11	1.395 (13)	C22—H22A	0.9500
C1—C2	1.345 (14)	C23—C24	1.376 (13)
C1—H1A	0.9500	C23—H23A	0.9500
C2—C3	1.365 (14)	C24—C25	1.377 (13)
C2—H2A	0.9500	C24—H24A	0.9500
C3—C4	1.368 (14)	C25—C26	1.477 (13)
C3—H3A	0.9500	C26—C27	1.380 (13)
C4—C5	1.401 (14)	C27—C28	1.406 (14)
C4—H4A	0.9500	C27—H27A	0.9500
C5—C6	1.462 (13)	C28—C29	1.350 (13)
C6—C7	1.381 (14)	C28—H28A	0.9500
C7—C8	1.396 (15)	C29—C30	1.392 (13)
C7—H7A	0.9500	C29—H29A	0.9500
C8—C9	1.356 (15)	C30—C31	1.506 (14)
C8—H8A	0.9500	C31—C32	1.287 (14)
C9—C10	1.386 (14)	C32—C33	1.377 (15)
C9—H9A	0.9500	C32—H32A	0.9500
C10—C11	1.478 (15)	C33—C34	1.408 (15)
C11—C12	1.352 (15)	C33—H33A	0.9500
C12—C13	1.364 (15)	C34—C35	1.379 (13)
C12—H12A	0.9500	C34—H34A	0.9500
C13—C14	1.381 (16)	C35—H35A	0.9500
C13—H13A	0.9500	Cl10—O13	1.388 (11)
C14—C15	1.370 (15)	Cl10—O14	1.415 (8)
C14—H14A	0.9500	Cl10—O12	1.428 (8)
C15—H15A	0.9500	Cl10—O11	1.453 (9)
Cu2—N22	1.944 (8)	Cl20—O23	1.403 (8)
Cu2—N21	2.018 (8)	Cl20—O21	1.429 (8)
Cu2—N23	2.028 (8)	Cl20—O24	1.429 (9)
Cu2—Cl2	2.226 (3)	Cl20—O22	1.435 (7)

N2—Cu1—N3	81.3 (4)	N22—Cu2—Cl2ⁱⁱ	92.6 (2)
N2—Cu1—N1	79.3 (3)	N21—Cu2—Cl2ⁱⁱ	97.1 (2)
N3—Cu1—N1	159.9 (3)	N23—Cu2—Cl2ⁱⁱ	89.9 (2)
N2—Cu1—Cl1ⁱ	178.5 (2)	Cl2—Cu2—Cl2ⁱⁱ	88.56 (9)
N3—Cu1—Cl1ⁱ	98.9 (3)	Cu2—Cl2—Cu2ⁱⁱ	91.44 (9)
N1—Cu1—Cl1ⁱ	100.3 (2)	C25—N21—C21	117.2 (8)
N2—Cu1—Cl1	92.9 (2)	C25—N21—Cu2	115.8 (6)
N3—Cu1—Cl1	87.7 (2)	C21—N21—Cu2	126.9 (6)
N1—Cu1—Cl1	98.9 (2)	C30—N22—C26	123.4 (9)
Cl1ⁱ—Cu1—Cl1	88.55 (9)	C30—N22—Cu2	117.8 (7)
Cu1ⁱ—Cl1—Cu1	91.45 (9)	C26—N22—Cu2	118.8 (6)
C1—N1—C5	118.0 (9)	C35—N23—C31	117.4 (9)
C1—N1—Cu1	128.2 (7)	C35—N23—Cu2	128.4 (7)
C5—N1—Cu1	113.7 (6)	C31—N23—Cu2	113.6 (7)
C6—N2—C10	121.9 (9)	N21—C21—C22	121.0 (9)
C6—N2—Cu1	120.3 (7)	N21—C21—H21A	119.5
C10—N2—Cu1	117.8 (8)	C22—C21—H21A	119.5
C15—N3—C11	117.3 (9)	C23—C22—C21	120.7 (9)
C15—N3—Cu1	129.0 (7)	C23—C22—H22A	119.6
C11—N3—Cu1	113.2 (7)	C21—C22—H22A	119.6
C2—C1—N1	122.7 (10)	C22—C23—C24	118.7 (9)
C2—C1—H1A	118.6	C22—C23—H23A	120.6
N1—C1—H1A	118.6	C24—C23—H23A	120.6
C1—C2—C3	119.8 (10)	C23—C24—C25	119.3 (9)
C1—C2—H2A	120.1	C23—C24—H24A	120.3
C3—C2—H2A	120.1	C25—C24—H24A	120.3
C2—C3—C4	120.2 (10)	N21—C25—C24	123.0 (9)
C2—C3—H3A	119.9	N21—C25—C26	113.1 (8)
C4—C3—H3A	119.9	C24—C25—C26	123.9 (9)
C3—C4—C5	119.0 (10)	N22—C26—C27	119.8 (9)
C3—C4—H4A	120.5	N22—C26—C25	112.9 (8)
C5—C4—H4A	120.5	C27—C26—C25	127.3 (9)
N1—C5—C4	120.2 (9)	C26—C27—C28	117.4 (9)
N1—C5—C6	114.1 (9)	C26—C27—H27A	121.3
C4—C5—C6	125.7 (9)	C28—C27—H27A	121.3
N2—C6—C7	120.9 (10)	C29—C28—C27	120.8 (10)
N2—C6—C5	112.5 (9)	C29—C28—H28A	119.6
C7—C6—C5	126.6 (10)	C27—C28—H28A	119.6
C6—C7—C8	117.4 (11)	C28—C29—C30	119.6 (10)
C6—C7—H7A	121.3	C28—C29—H29A	120.2
C8—C7—H7A	121.3	C30—C29—H29A	120.2
C9—C8—C7	121.1 (11)	N22—C30—C29	118.9 (9)
C9—C8—H8A	119.5	N22—C30—C31	115.2 (9)
C7—C8—H8A	119.5	C29—C30—C31	125.9 (9)
C8—C9—C10	118.9 (11)	C32—C31—N23	121.6 (10)
C8—C9—H9A	120.6	C32—C31—C30	127.0 (10)
C10—C9—H9A	120.6	N23—C31—C30	111.4 (9)
N2—C10—C9	119.7 (11)	C31—C32—C33	122.7 (11)
N2—C10—C11	114.1 (10)	C31—C32—H32A	118.7
C9—C10—C11	126.2 (10)	C33—C32—H32A	118.7
C12—C11—N3	121.0 (10)	C32—C33—C34	116.8 (10)
C12—C11—C10	125.9 (10)	C32—C33—H33A	121.6
N3—C11—C10	113.0 (9)	C34—C33—H33A	121.6
C11—C12—C13	121.6 (11)	C35—C34—C33	118.0 (10)
C11—C12—H12A	119.2	C35—C34—H34A	121.0
C13—C12—H12A	119.2	C33—C34—H34A	121.0
C12—C13—C14	117.1 (11)	N23—C35—C34	123.3 (9)
C12—C13—H13A	121.5	N23—C35—H35A	118.3
C14—C13—H13A	121.5	C34—C35—H35A	118.3
C15—C14—C13	120.6 (11)	O13—Cl10—O14	111.8 (8)
C15—C14—H14A	119.7	O13—Cl10—O12	108.0 (7)
C13—C14—H14A	119.7	O14—Cl10—O12	109.6 (5)
N3—C15—C14	122.2 (10)	O13—Cl10—O11	109.3 (7)
N3—C15—H15A	118.9	O14—Cl10—O11	109.1 (5)
C14—C15—H15A	118.9	O12—Cl10—O11	109.0 (6)
N22—Cu2—N21	79.3 (3)	O23—Cl20—O21	111.1 (5)
N22—Cu2—N23	81.2 (3)	O23—Cl20—O24	111.5 (7)
N21—Cu2—N23	159.6 (3)	O21—Cl20—O24	108.7 (5)
N22—Cu2—Cl2	178.8 (2)	O23—Cl20—O22	108.4 (5)
N21—Cu2—Cl2	100.5 (2)	O21—Cl20—O22	109.5 (5)
N23—Cu2—Cl2	98.9 (2)	O24—Cl20—O22	107.4 (6)

N2—Cu1—Cl1—Cu1ⁱ	−179.9 (3)	N22—Cu2—Cl2—Cu2ⁱⁱ	−179 (100)
N3—Cu1—Cl1—Cu1ⁱ	98.9 (3)	N21—Cu2—Cl2—Cu2ⁱⁱ	−97.0 (2)
N1—Cu1—Cl1—Cu1ⁱ	−100.2 (2)	N23—Cu2—Cl2—Cu2ⁱⁱ	89.6 (2)
Cl1ⁱ—Cu1—Cl1—Cu1ⁱ	0.0	Cl2ⁱⁱ—Cu2—Cl2—Cu2ⁱⁱ	0.0
N2—Cu1—N1—C1	180.0 (8)	N22—Cu2—N21—C25	−3.0 (7)
N3—Cu1—N1—C1	−163.6 (9)	N23—Cu2—N21—C25	−20.8 (13)
Cl1ⁱ—Cu1—N1—C1	−1.5 (8)	Cl2—Cu2—N21—C25	178.2 (6)
Cl1—Cu1—N1—C1	88.7 (8)	Cl2ⁱⁱ—Cu2—N21—C25	88.3 (7)
N2—Cu1—N1—C5	3.2 (6)	N22—Cu2—N21—C21	−178.5 (8)
N3—Cu1—N1—C5	19.6 (13)	N23—Cu2—N21—C21	163.7 (8)
Cl1ⁱ—Cu1—N1—C5	−178.3 (6)	Cl2—Cu2—N21—C21	2.7 (8)
Cl1—Cu1—N1—C5	−88.2 (6)	Cl2ⁱⁱ—Cu2—N21—C21	−87.2 (8)
N3—Cu1—N2—C6	−177.3 (7)	N21—Cu2—N22—C30	−176.8 (7)
N1—Cu1—N2—C6	−3.0 (7)	N23—Cu2—N22—C30	−3.0 (7)
Cl1ⁱ—Cu1—N2—C6	−79 (11)	Cl2—Cu2—N22—C30	−95 (12)
Cl1—Cu1—N2—C6	95.5 (7)	Cl2ⁱⁱ—Cu2—N22—C30	86.5 (7)
N3—Cu1—N2—C10	4.4 (7)	N21—Cu2—N22—C26	1.6 (7)
N1—Cu1—N2—C10	178.7 (8)	N23—Cu2—N22—C26	175.4 (7)
Cl1ⁱ—Cu1—N2—C10	103 (11)	Cl2—Cu2—N22—C26	84 (12)
Cl1—Cu1—N2—C10	−82.8 (7)	Cl2ⁱⁱ—Cu2—N22—C26	−95.2 (7)
N2—Cu1—N3—C15	−179.0 (8)	N22—Cu2—N23—C35	178.4 (8)
N1—Cu1—N3—C15	164.6 (8)	N21—Cu2—N23—C35	−163.9 (8)
Cl1ⁱ—Cu1—N3—C15	2.5 (8)	Cl2—Cu2—N23—C35	−2.8 (8)
Cl1—Cu1—N3—C15	−85.7 (8)	Cl2ⁱⁱ—Cu2—N23—C35	85.7 (8)
N2—Cu1—N3—C11	−6.5 (6)	N22—Cu2—N23—C31	7.5 (6)
N1—Cu1—N3—C11	−22.9 (13)	N21—Cu2—N23—C31	25.2 (13)
Cl1ⁱ—Cu1—N3—C11	174.9 (6)	Cl2—Cu2—N23—C31	−173.7 (6)
Cl1—Cu1—N3—C11	86.8 (6)	Cl2ⁱⁱ—Cu2—N23—C31	−85.2 (6)
C5—N1—C1—C2	1.0 (14)	C25—N21—C21—C22	−0.9 (14)
Cu1—N1—C1—C2	−175.7 (7)	Cu2—N21—C21—C22	174.5 (7)
N1—C1—C2—C3	−0.9 (15)	N21—C21—C22—C23	−1.1 (15)
C1—C2—C3—C4	0.8 (15)	C21—C22—C23—C24	2.8 (16)
C2—C3—C4—C5	−0.8 (15)	C22—C23—C24—C25	−2.6 (16)
C1—N1—C5—C4	−1.0 (13)	C21—N21—C25—C24	1.1 (14)
Cu1—N1—C5—C4	176.1 (7)	Cu2—N21—C25—C24	−174.8 (8)
C1—N1—C5—C6	179.8 (8)	C21—N21—C25—C26	179.7 (8)
Cu1—N1—C5—C6	−3.0 (10)	Cu2—N21—C25—C26	3.8 (11)
C3—C4—C5—N1	1.0 (15)	C23—C24—C25—N21	0.6 (16)
C3—C4—C5—C6	−180.0 (9)	C23—C24—C25—C26	−177.9 (10)
C10—N2—C6—C7	−0.8 (14)	C30—N22—C26—C27	−1.2 (14)
Cu1—N2—C6—C7	−179.1 (7)	Cu2—N22—C26—C27	−179.4 (7)
C10—N2—C6—C5	−179.6 (8)	C30—N22—C26—C25	178.2 (8)
Cu1—N2—C6—C5	2.1 (10)	Cu2—N22—C26—C25	0.0 (11)
N1—C5—C6—N2	0.8 (12)	N21—C25—C26—N22	−2.5 (12)
C4—C5—C6—N2	−178.3 (9)	C24—C25—C26—N22	176.1 (9)
N1—C5—C6—C7	−178.0 (9)	N21—C25—C26—C27	176.9 (9)
C4—C5—C6—C7	3.0 (16)	C24—C25—C26—C27	−4.5 (17)
N2—C6—C7—C8	1.5 (14)	N22—C26—C27—C28	−0.9 (14)
C5—C6—C7—C8	−179.9 (9)	C25—C26—C27—C28	179.8 (9)
C6—C7—C8—C9	−3.0 (16)	C26—C27—C28—C29	2.3 (15)
C7—C8—C9—C10	3.9 (16)	C27—C28—C29—C30	−1.7 (16)
C6—N2—C10—C9	1.7 (14)	C26—N22—C30—C29	1.9 (15)
Cu1—N2—C10—C9	180.0 (7)	Cu2—N22—C30—C29	−179.9 (7)
C6—N2—C10—C11	−179.7 (8)	C26—N22—C30—C31	179.9 (8)
Cu1—N2—C10—C11	−1.4 (11)	Cu2—N22—C30—C31	−1.8 (11)
C8—C9—C10—N2	−3.1 (15)	C28—C29—C30—N22	−0.4 (15)
C8—C9—C10—C11	178.4 (9)	C28—C29—C30—C31	−178.2 (9)
C15—N3—C11—C12	3.7 (13)	C35—N23—C31—C32	−1.2 (14)
Cu1—N3—C11—C12	−169.7 (7)	Cu2—N23—C31—C32	170.8 (8)
C15—N3—C11—C10	−179.1 (8)	C35—N23—C31—C30	178.0 (8)
Cu1—N3—C11—C10	7.5 (10)	Cu2—N23—C31—C30	−10.1 (10)
N2—C10—C11—C12	172.8 (9)	N22—C30—C31—C32	−172.9 (10)
C9—C10—C11—C12	−8.7 (16)	C29—C30—C31—C32	5.0 (17)
N2—C10—C11—N3	−4.2 (12)	N22—C30—C31—N23	7.9 (12)
C9—C10—C11—N3	174.3 (9)	C29—C30—C31—N23	−174.2 (9)
N3—C11—C12—C13	−0.1 (15)	N23—C31—C32—C33	−1.2 (16)
C10—C11—C12—C13	−176.9 (9)	C30—C31—C32—C33	179.8 (10)
C11—C12—C13—C14	−4.1 (15)	C31—C32—C33—C34	4.2 (16)
C12—C13—C14—C15	4.7 (15)	C32—C33—C34—C35	−4.8 (15)
C11—N3—C15—C14	−3.1 (14)	C31—N23—C35—C34	0.3 (14)
Cu1—N3—C15—C14	169.1 (7)	Cu2—N23—C35—C34	−170.3 (7)
C13—C14—C15—N3	−1.2 (16)	C33—C34—C35—N23	2.7 (15)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O22ⁱⁱⁱ	0.95	2.47	3.316 (14)	149
C4—H4A···O23ⁱⁱⁱ	0.95	2.59	3.219 (15)	124
C9—H9A···O11^iv	0.95	2.37	3.309 (14)	172
C12—H12A···O12^iv	0.95	2.42	3.172 (14)	137
C13—H13A···O12^v	0.95	2.37	3.160 (15)	140
C22—H22A···Cl2^vi	0.95	2.82	3.490 (10)	129
C24—H24A···O11	0.95	2.57	3.133 (12)	118
C24—H24A···O14	0.95	2.51	3.360 (14)	149
C27—H27A···O14	0.95	2.55	3.429 (13)	153
C29—H29A···O22^iv	0.95	2.48	3.421 (13)	170
C32—H32A···O21^iv	0.95	2.47	3.254 (13)	140
C33—H33A···O21^vii	0.95	2.46	3.194 (14)	134

Symmetry codes: (iii) x+1, y+1, z; (iv) x−1, y, z; (v) −x+1, −y+1, −z+1; (vi) −x+2, −y+1, −z; (vii) −x, −y, −z.

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