A structure with trigonally and tetra­hedrally coordinated CuI cations: rac-(acetonitrile)[2,2′-bis­(1-propyl-1H-benzimidazol-2-yl)biphenyl]copper(I) bis­(acetonitrile)[2,2′-bis­(1-propyl-1H-benzimidazol-2-yl)biphenyl]copper(I) bis­(perchlorate)

Stibrany, R.T.; Potenza, J.A.

doi:10.1107/S1600536806047386

A structure with trigonally and tetrahedrally coordinated Cu^I cations: rac-(acetonitrile)[2,2′-bis(1-propyl-1H-benzimidazol-2-yl)biphenyl]copper(I) bis(acetonitrile)[2,2′-bis(1-propyl-1H-benzimidazol-2-yl)biphenyl]copper(I) bis(perchlorate)

The asymmetric unit of the title salt, [Cu(C₃₂H₃₀N₄)(C₂H₃N)][Cu(C₃₂H₃₀N₄)(C₂H₃N)₂](ClO₄)₂, contains two perchlorate anions and two crystallographically distinct Cu^I complexes, viz. [Cu(L1b)(acetonitrile)]⁺ (A) and [Cu(L1b)(acetonitrile)₂]⁺ (B), where L1b is 2,2′-bis(1-propylbenzimidazol-2-yl)biphenyl. The A and B cations exhibit approximate trigonal–planar and tetrahedral coordination geometries, respectively. In the solid state, the ligand L1b is chiral but the crystal structure is a racemate. The cations form separate, enantiomerically pure columns along the a-axis direction. Centrosymmetrically related alternating R and S columns of A and of B cations, centered about the planes y = 0 and y = ${1 \over 2}$ , respectively, progress along the c-axis direction. The perchlorate ions, which form columns along the a-axis direction, are linked to the cations by C—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047386/sg2094sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047386/sg2094Isup2.hkl Contains datablock I

CCDC reference: 630460

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.005 Å
R factor = 0.051
wR factor = 0.145
Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.24 Ratio
PLAT221_ALERT_4_B Large Solvent/Anion  O     Ueq(max)/Ueq(min) ...       4.03 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.52 Ratio

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.867     1.000
            Tmin and Tmax expected:      0.720     0.947
            RR =      1.140
            Please check that your absorption correction is appropriate.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.14
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.95
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.13 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    N     Ueq(max)/Ueq(min) ...       2.89 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.23 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   N52     ..       5.53 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        N51
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        N52
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      47.00 A   3 
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         12

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.947
            Tmax scaled      0.947 Tmin scaled      0.821

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2000).

rac-(acetonitrile)[2,2'-bis(1-propyl-1H-benzimidazol-2-yl)biphenyl]copper(I) bis(acetonitrile)[2,2'-bis(1-propyl-1H-benzimidazol-2-yl)biphenyl]copper(I) bis(perchlorate) top

Crystal data top

[Cu(C₃₂H₃₀N₄)(C₂H₃N)][Cu(C₃₂H₃₀N₄)(C₂H₃N)₂](ClO₄)₂	Z = 2
M_r = 1390.34	F(000) = 1444
Triclinic, P1	D_x = 1.389 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8593 (15) Å	Cell parameters from 975 reflections
b = 17.407 (3) Å	θ = 5.2–49.9°
c = 22.760 (4) Å	µ = 0.78 mm⁻¹
α = 71.424 (3)°	T = 100 K
β = 87.901 (3)°	Plate, colorless
γ = 88.588 (3)°	0.43 × 0.38 × 0.07 mm
V = 3324.5 (10) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	11757 independent reflections
Radiation source: fine-focus sealed tube	9415 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scans	θ_max = 25.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Blessing, 1995)	h = −10→10
T_min = 0.867, T_max = 1.00	k = −20→20
26871 measured reflections	l = −27→27

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) = 0.145	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0813P)² + 6.3573P] where P = (F_o² + 2F_c²)/3
11757 reflections	(Δ/σ)_max = 0.001
823 parameters	Δρ_max = 1.14 e Å⁻³
16 restraints	Δρ_min = −1.20 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	0.71596 (5)	0.55291 (3)	0.222723 (19)	0.02283 (12)
N11	0.8186 (4)	0.37040 (17)	0.14127 (13)	0.0245 (7)
N13	0.7383 (3)	0.45708 (17)	0.19026 (13)	0.0203 (6)
N41	0.8808 (3)	0.77329 (17)	0.10137 (13)	0.0211 (6)
N43	0.8092 (3)	0.66157 (16)	0.17690 (13)	0.0193 (6)
N51	0.4932 (4)	0.5907 (3)	0.2175 (2)	0.0561 (8)
N52	0.7795 (6)	0.5157 (2)	0.31249 (18)	0.0554 (7)
C11	0.6832 (5)	0.3409 (2)	0.17035 (16)	0.0277 (8)
C12	0.8464 (4)	0.4398 (2)	0.15476 (15)	0.0206 (7)
C13	0.6343 (4)	0.3952 (2)	0.20166 (15)	0.0231 (7)
C14	0.5000 (4)	0.3819 (2)	0.23682 (17)	0.0302 (9)
H14	0.4670	0.4166	0.2585	0.036*
C15	0.4173 (5)	0.3145 (3)	0.23808 (18)	0.0381 (10)
H15	0.3269	0.3043	0.2611	0.046*
C16	0.4655 (6)	0.2619 (3)	0.20600 (19)	0.0458 (12)
H16	0.4062	0.2177	0.2080	0.055*
C17	0.5993 (5)	0.2736 (2)	0.17134 (18)	0.0374 (10)
H17	0.6317	0.2386	0.1498	0.045*
C18	0.9142 (5)	0.3323 (2)	0.10389 (18)	0.0358 (10)
H18A	0.9836	0.3720	0.0778	0.043*
H18B	0.8511	0.3141	0.0771	0.043*
C19	1.0041 (6)	0.2600 (2)	0.14498 (19)	0.0413 (11)
H19A	1.0709	0.2788	0.1702	0.050*
H19B	0.9348	0.2218	0.1727	0.050*
C1A	1.0964 (6)	0.2173 (3)	0.1074 (2)	0.0525 (13)
H1A1	1.0301	0.1939	0.0855	0.079*
H1A2	1.1569	0.1753	0.1346	0.079*
H1A3	1.1610	0.2556	0.0782	0.079*
C21	0.9698 (4)	0.5654 (2)	0.08709 (15)	0.0184 (7)
C22	0.9837 (4)	0.4883 (2)	0.13090 (15)	0.0205 (7)
C23	1.1248 (4)	0.4586 (2)	0.15218 (17)	0.0268 (8)
H23	1.1334	0.4077	0.1818	0.032*
C24	1.2527 (4)	0.5036 (2)	0.12983 (18)	0.0297 (8)
H24	1.3473	0.4825	0.1436	0.036*
C25	1.2400 (4)	0.5800 (2)	0.08697 (17)	0.0281 (8)
H25	1.3260	0.6105	0.0719	0.034*
C26	1.0995 (4)	0.6113 (2)	0.06645 (16)	0.0227 (7)
H26	1.0914	0.6634	0.0386	0.027*
C31	0.8228 (4)	0.5980 (2)	0.05928 (14)	0.0183 (7)
C32	0.7539 (4)	0.6661 (2)	0.06971 (15)	0.0192 (7)
C33	0.6263 (4)	0.7009 (2)	0.03717 (16)	0.0227 (7)
H33	0.5811	0.7464	0.0437	0.027*
C34	0.5658 (4)	0.6682 (2)	−0.00502 (16)	0.0247 (8)
H34	0.4819	0.6926	−0.0273	0.030*
C35	0.6309 (4)	0.5994 (2)	−0.01381 (16)	0.0252 (8)
H35	0.5885	0.5764	−0.0410	0.030*
C36	0.7587 (4)	0.5647 (2)	0.01780 (15)	0.0215 (7)
H36	0.8024	0.5188	0.0114	0.026*
C41	0.9202 (4)	0.7842 (2)	0.15635 (16)	0.0204 (7)
C42	0.8145 (4)	0.69924 (19)	0.11620 (15)	0.0179 (7)
C43	0.8733 (4)	0.7148 (2)	0.20305 (15)	0.0196 (7)
C44	0.8912 (4)	0.7085 (2)	0.26542 (17)	0.0280 (8)
H44	0.8577	0.6634	0.2974	0.034*
C45	0.9606 (4)	0.7717 (2)	0.27748 (18)	0.0300 (8)
H45	0.9728	0.7692	0.3185	0.036*
C46	1.0130 (4)	0.8394 (2)	0.22983 (19)	0.0314 (9)
H46	1.0626	0.8798	0.2399	0.038*
C47	0.9929 (4)	0.8478 (2)	0.16834 (18)	0.0265 (8)
H47	1.0259	0.8933	0.1366	0.032*
C48	0.9064 (4)	0.8320 (2)	0.03978 (16)	0.0249 (8)
H48A	0.8982	0.8048	0.0089	0.030*
H48B	1.0083	0.8523	0.0367	0.030*
C49	0.7952 (4)	0.9033 (2)	0.02540 (17)	0.0273 (8)
H49A	0.6931	0.8836	0.0271	0.033*
H49B	0.8015	0.9303	0.0565	0.033*
C4A	0.8288 (5)	0.9634 (2)	−0.03837 (18)	0.0340 (9)
H4A1	0.9338	0.9769	−0.0421	0.051*
H4A2	0.7685	1.0116	−0.0437	0.051*
H4A3	0.8052	0.9396	−0.0696	0.051*
C51	0.3872 (5)	0.6295 (3)	0.2042 (3)	0.0561 (8)
C52	0.2523 (5)	0.6813 (3)	0.1864 (3)	0.0561 (8)
H52A	0.2396	0.7148	0.2126	0.084*
H52B	0.1651	0.6480	0.1910	0.084*
H52C	0.2638	0.7150	0.1440	0.084*
C53	0.8338 (7)	0.5010 (3)	0.3602 (2)	0.0554 (7)
C54	0.9078 (7)	0.4816 (3)	0.4198 (2)	0.0554 (7)
H54A	0.9269	0.4243	0.4357	0.083*
H54B	0.8434	0.4980	0.4486	0.083*
H54C	1.0017	0.5099	0.4140	0.083*
Cu2	0.19512 (5)	1.04191 (2)	0.285046 (19)	0.02090 (12)
N53	0.0065 (4)	1.04503 (18)	0.24117 (14)	0.0268 (7)
N61	0.3866 (3)	0.81477 (17)	0.33001 (13)	0.0209 (6)
N63	0.3085 (3)	0.94257 (16)	0.28742 (12)	0.0186 (6)
N91	0.3282 (3)	1.17827 (16)	0.39282 (12)	0.0175 (6)
N93	0.2293 (3)	1.11581 (16)	0.33158 (12)	0.0184 (6)
C55	−0.1070 (4)	1.0305 (2)	0.22664 (17)	0.0277 (8)
C56	−0.2544 (5)	1.0103 (3)	0.2095 (2)	0.0421 (10)
H56A	−0.2677	0.9527	0.2254	0.063*
H56B	−0.2603	1.0280	0.1651	0.063*
H56C	−0.3323	1.0368	0.2267	0.063*
C61	0.4311 (4)	0.8373 (2)	0.26794 (16)	0.0219 (7)
C62	0.3152 (4)	0.8799 (2)	0.33911 (15)	0.0190 (7)
C63	0.3802 (4)	0.9167 (2)	0.24143 (16)	0.0210 (7)
C64	0.4043 (4)	0.9578 (2)	0.17859 (16)	0.0248 (8)
H64	0.3696	1.0108	0.1608	0.030*
C65	0.4818 (4)	0.9166 (2)	0.14375 (17)	0.0295 (8)
H65	0.4993	0.9421	0.1015	0.035*
C66	0.5345 (4)	0.8371 (3)	0.17120 (18)	0.0323 (9)
H66	0.5865	0.8111	0.1465	0.039*
C67	0.5124 (4)	0.7959 (2)	0.23318 (18)	0.0290 (8)
H67	0.5494	0.7435	0.2511	0.035*
C68	0.4207 (5)	0.7366 (2)	0.37663 (18)	0.0302 (8)
H68A	0.4057	0.7418	0.4176	0.036*
H68B	0.5262	0.7227	0.3718	0.036*
C69	0.3223 (5)	0.6677 (3)	0.3717 (2)	0.0461 (11)
H69A	0.2173	0.6793	0.3796	0.055*
H69B	0.3319	0.6645	0.3300	0.055*
C6A	0.3680 (8)	0.5874 (3)	0.4173 (3)	0.0752 (18)
H6A1	0.4734	0.5772	0.4111	0.113*
H6A2	0.3096	0.5451	0.4112	0.113*
H6A3	0.3502	0.5890	0.4588	0.113*
C71	0.3148 (4)	0.9389 (2)	0.42487 (15)	0.0184 (7)
C72	0.2511 (4)	0.8847 (2)	0.39875 (15)	0.0193 (7)
C73	0.1222 (4)	0.8421 (2)	0.42624 (16)	0.0230 (7)
H73	0.0811	0.8056	0.4092	0.028*
C74	0.0550 (4)	0.8536 (2)	0.47846 (17)	0.0267 (8)
H74	−0.0304	0.8245	0.4967	0.032*
C75	0.1144 (4)	0.9086 (2)	0.50376 (16)	0.0240 (8)
H75	0.0673	0.9174	0.5383	0.029*
C76	0.2445 (4)	0.9506 (2)	0.47749 (15)	0.0215 (7)
H76	0.2851	0.9868	0.4950	0.026*
C81	0.4605 (4)	0.9785 (2)	0.40014 (15)	0.0189 (7)
C82	0.4777 (4)	1.0623 (2)	0.37614 (14)	0.0183 (7)
C83	0.6208 (4)	1.0945 (2)	0.35752 (16)	0.0228 (7)
H83	0.6320	1.1504	0.3417	0.027*
C84	0.7458 (4)	1.0444 (2)	0.36236 (16)	0.0249 (8)
H84	0.8409	1.0666	0.3506	0.030*
C85	0.7298 (4)	0.9606 (2)	0.38476 (16)	0.0246 (8)
H85	0.8136	0.9266	0.3873	0.030*
C86	0.5881 (4)	0.9286 (2)	0.40313 (15)	0.0205 (7)
H86	0.5773	0.8726	0.4178	0.025*
C91	0.1932 (4)	1.2187 (2)	0.37213 (15)	0.0204 (7)
C92	0.3444 (4)	1.1175 (2)	0.36693 (14)	0.0177 (7)
C93	0.1333 (4)	1.1792 (2)	0.33386 (15)	0.0192 (7)
C94	−0.0017 (4)	1.2067 (2)	0.30397 (16)	0.0248 (8)
H94	−0.0435	1.1809	0.2785	0.030*
C95	−0.0708 (4)	1.2736 (2)	0.31356 (17)	0.0293 (8)
H95	−0.1606	1.2935	0.2940	0.035*
C96	−0.0087 (5)	1.3121 (2)	0.35193 (18)	0.0313 (9)
H96	−0.0587	1.3572	0.3573	0.038*
C97	0.1235 (4)	1.2860 (2)	0.38221 (17)	0.0273 (8)
H97	0.1640	1.3118	0.4079	0.033*
C98	0.4300 (4)	1.2006 (2)	0.43377 (15)	0.0225 (7)
H98A	0.5008	1.1563	0.4506	0.027*
H98B	0.3714	1.2088	0.4682	0.027*
C99	0.5176 (4)	1.2771 (2)	0.40089 (17)	0.0270 (8)
H99A	0.5819	1.2681	0.3682	0.032*
H99B	0.4474	1.3209	0.3819	0.032*
C9A	0.6140 (5)	1.3014 (3)	0.4456 (2)	0.0414 (10)
H9A1	0.5500	1.3143	0.4762	0.062*
H9A2	0.6722	1.3480	0.4233	0.062*
H9A3	0.6808	1.2574	0.4657	0.062*
Cl1	0.31761 (10)	0.85586 (5)	0.96326 (4)	0.0287 (2)
O11	0.2084 (4)	0.91820 (18)	0.94188 (15)	0.0487 (8)
O12	0.4367 (5)	0.8599 (3)	0.9205 (2)	0.108 (2)
O13	0.3775 (9)	0.8618 (5)	1.0159 (3)	0.196 (5)
O14	0.2509 (5)	0.7816 (2)	0.9757 (4)	0.135 (3)
Cl2	0.81011 (10)	0.67043 (5)	0.45767 (4)	0.0253 (2)
O21	0.7709 (3)	0.75449 (17)	0.44548 (15)	0.0388 (7)
O22	0.7520 (4)	0.6424 (2)	0.41043 (15)	0.0523 (9)
O23	0.9703 (3)	0.66080 (18)	0.45839 (17)	0.0492 (8)
O24	0.7479 (4)	0.6241 (2)	0.51579 (15)	0.0513 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0286 (2)	0.0189 (2)	0.0208 (2)	−0.00218 (17)	0.00206 (17)	−0.00627 (17)
N11	0.0400 (18)	0.0181 (15)	0.0159 (14)	−0.0033 (13)	−0.0010 (13)	−0.0058 (12)
N13	0.0245 (15)	0.0168 (14)	0.0186 (14)	−0.0012 (12)	−0.0017 (12)	−0.0041 (11)
N41	0.0267 (16)	0.0176 (14)	0.0184 (14)	−0.0016 (12)	0.0007 (12)	−0.0050 (12)
N43	0.0233 (15)	0.0176 (14)	0.0172 (14)	−0.0001 (12)	−0.0008 (11)	−0.0055 (11)
N51	0.0334 (13)	0.0672 (19)	0.092 (2)	0.0077 (12)	−0.0118 (14)	−0.0597 (17)
N52	0.097 (2)	0.0310 (13)	0.0408 (14)	0.0040 (13)	−0.0252 (14)	−0.0125 (11)
C11	0.043 (2)	0.0219 (18)	0.0152 (17)	−0.0068 (16)	−0.0052 (15)	−0.0003 (14)
C12	0.0294 (19)	0.0148 (16)	0.0164 (16)	0.0002 (14)	−0.0053 (14)	−0.0029 (13)
C13	0.0293 (19)	0.0214 (18)	0.0150 (16)	−0.0052 (15)	−0.0063 (14)	0.0002 (14)
C14	0.033 (2)	0.031 (2)	0.0197 (18)	−0.0062 (17)	−0.0056 (15)	0.0018 (15)
C15	0.037 (2)	0.043 (2)	0.023 (2)	−0.0167 (19)	−0.0045 (17)	0.0056 (18)
C16	0.066 (3)	0.035 (2)	0.029 (2)	−0.030 (2)	−0.013 (2)	0.0052 (18)
C17	0.061 (3)	0.025 (2)	0.024 (2)	−0.0161 (19)	−0.0057 (19)	−0.0039 (16)
C18	0.062 (3)	0.023 (2)	0.025 (2)	−0.0050 (19)	0.0093 (19)	−0.0128 (16)
C19	0.072 (3)	0.024 (2)	0.027 (2)	−0.001 (2)	0.008 (2)	−0.0090 (17)
C1A	0.080 (4)	0.035 (2)	0.043 (3)	−0.002 (2)	0.021 (2)	−0.014 (2)
C21	0.0230 (17)	0.0205 (17)	0.0156 (16)	−0.0004 (14)	0.0018 (13)	−0.0112 (13)
C22	0.0276 (18)	0.0194 (17)	0.0170 (16)	−0.0001 (14)	0.0012 (14)	−0.0094 (13)
C23	0.035 (2)	0.0224 (18)	0.0240 (18)	0.0050 (16)	−0.0021 (15)	−0.0092 (15)
C24	0.0246 (19)	0.037 (2)	0.032 (2)	0.0075 (16)	−0.0041 (16)	−0.0174 (17)
C25	0.0229 (19)	0.038 (2)	0.0263 (19)	−0.0047 (16)	0.0036 (15)	−0.0137 (17)
C26	0.0268 (19)	0.0245 (18)	0.0173 (17)	−0.0044 (15)	0.0046 (14)	−0.0077 (14)
C31	0.0235 (17)	0.0171 (16)	0.0124 (15)	−0.0039 (13)	0.0043 (13)	−0.0025 (13)
C32	0.0238 (18)	0.0199 (17)	0.0136 (16)	−0.0031 (14)	0.0033 (13)	−0.0049 (13)
C33	0.0235 (18)	0.0222 (18)	0.0219 (18)	−0.0010 (14)	0.0028 (14)	−0.0068 (14)
C34	0.0209 (18)	0.031 (2)	0.0216 (18)	0.0002 (15)	−0.0035 (14)	−0.0076 (15)
C35	0.0268 (19)	0.031 (2)	0.0207 (18)	−0.0076 (15)	0.0016 (14)	−0.0124 (15)
C36	0.0262 (18)	0.0202 (17)	0.0195 (17)	−0.0025 (14)	0.0028 (14)	−0.0088 (14)
C41	0.0224 (17)	0.0187 (17)	0.0216 (17)	0.0023 (14)	−0.0018 (14)	−0.0084 (14)
C42	0.0185 (16)	0.0154 (16)	0.0208 (17)	0.0009 (13)	0.0006 (13)	−0.0074 (13)
C43	0.0215 (17)	0.0182 (17)	0.0209 (17)	0.0008 (13)	−0.0037 (13)	−0.0087 (14)
C44	0.039 (2)	0.0237 (19)	0.0218 (18)	0.0031 (16)	−0.0065 (16)	−0.0067 (15)
C45	0.035 (2)	0.034 (2)	0.0253 (19)	0.0029 (17)	−0.0094 (16)	−0.0150 (17)
C46	0.033 (2)	0.026 (2)	0.042 (2)	−0.0006 (16)	−0.0092 (17)	−0.0185 (18)
C47	0.028 (2)	0.0199 (18)	0.032 (2)	−0.0031 (15)	−0.0009 (16)	−0.0090 (15)
C48	0.032 (2)	0.0219 (18)	0.0207 (18)	−0.0028 (15)	0.0033 (15)	−0.0067 (14)
C49	0.033 (2)	0.0224 (19)	0.0245 (19)	−0.0017 (15)	−0.0015 (15)	−0.0051 (15)
C4A	0.044 (2)	0.028 (2)	0.027 (2)	0.0047 (18)	−0.0051 (17)	−0.0048 (17)
C51	0.0334 (13)	0.0672 (19)	0.092 (2)	0.0077 (12)	−0.0118 (14)	−0.0597 (17)
C52	0.0334 (13)	0.0672 (19)	0.092 (2)	0.0077 (12)	−0.0118 (14)	−0.0597 (17)
C53	0.097 (2)	0.0310 (13)	0.0408 (14)	0.0040 (13)	−0.0252 (14)	−0.0125 (11)
C54	0.097 (2)	0.0310 (13)	0.0408 (14)	0.0040 (13)	−0.0252 (14)	−0.0125 (11)
Cu2	0.0244 (2)	0.0187 (2)	0.0207 (2)	−0.00103 (17)	−0.00305 (17)	−0.00762 (17)
N53	0.0282 (18)	0.0246 (16)	0.0308 (17)	0.0022 (13)	−0.0083 (14)	−0.0126 (13)
N61	0.0246 (15)	0.0195 (15)	0.0201 (15)	−0.0013 (12)	−0.0022 (12)	−0.0081 (12)
N63	0.0206 (14)	0.0202 (15)	0.0166 (14)	0.0001 (12)	−0.0029 (11)	−0.0079 (12)
N91	0.0234 (15)	0.0167 (14)	0.0125 (13)	−0.0015 (11)	−0.0017 (11)	−0.0046 (11)
N93	0.0231 (15)	0.0155 (14)	0.0158 (14)	−0.0030 (11)	0.0000 (11)	−0.0037 (11)
C55	0.033 (2)	0.0257 (19)	0.0266 (19)	0.0015 (16)	−0.0061 (16)	−0.0104 (16)
C56	0.034 (2)	0.052 (3)	0.046 (3)	−0.002 (2)	−0.0145 (19)	−0.022 (2)
C61	0.0206 (17)	0.0254 (18)	0.0219 (18)	0.0005 (14)	−0.0027 (14)	−0.0104 (15)
C62	0.0197 (17)	0.0188 (17)	0.0201 (17)	−0.0015 (13)	−0.0032 (13)	−0.0080 (14)
C63	0.0183 (17)	0.0280 (19)	0.0199 (17)	−0.0008 (14)	−0.0033 (13)	−0.0119 (14)
C64	0.0247 (19)	0.030 (2)	0.0196 (17)	0.0009 (15)	−0.0033 (14)	−0.0081 (15)
C65	0.0263 (19)	0.043 (2)	0.0208 (18)	0.0008 (17)	−0.0007 (15)	−0.0124 (17)
C66	0.027 (2)	0.045 (2)	0.032 (2)	0.0061 (17)	0.0034 (16)	−0.0232 (18)
C67	0.028 (2)	0.029 (2)	0.033 (2)	0.0047 (16)	−0.0041 (16)	−0.0134 (17)
C68	0.040 (2)	0.0218 (19)	0.028 (2)	0.0054 (16)	−0.0042 (17)	−0.0063 (16)
C69	0.045 (3)	0.025 (2)	0.062 (3)	−0.0043 (19)	0.000 (2)	−0.004 (2)
C6A	0.102 (5)	0.035 (3)	0.081 (4)	−0.011 (3)	−0.008 (4)	−0.006 (3)
C71	0.0217 (17)	0.0177 (16)	0.0144 (16)	0.0016 (13)	−0.0025 (13)	−0.0030 (13)
C72	0.0231 (17)	0.0176 (17)	0.0169 (16)	−0.0004 (13)	−0.0018 (13)	−0.0050 (13)
C73	0.0264 (19)	0.0218 (18)	0.0214 (18)	−0.0037 (14)	−0.0043 (14)	−0.0073 (14)
C74	0.0236 (19)	0.031 (2)	0.0235 (18)	−0.0077 (15)	0.0006 (14)	−0.0046 (15)
C75	0.0242 (18)	0.031 (2)	0.0157 (17)	0.0002 (15)	0.0028 (14)	−0.0068 (15)
C76	0.0264 (18)	0.0199 (17)	0.0190 (17)	−0.0002 (14)	−0.0035 (14)	−0.0070 (14)
C81	0.0230 (18)	0.0223 (18)	0.0135 (16)	−0.0023 (14)	−0.0036 (13)	−0.0082 (13)
C82	0.0232 (17)	0.0212 (17)	0.0125 (15)	−0.0005 (14)	−0.0020 (13)	−0.0079 (13)
C83	0.0265 (19)	0.0223 (18)	0.0201 (17)	−0.0061 (14)	0.0005 (14)	−0.0074 (14)
C84	0.0213 (18)	0.034 (2)	0.0211 (18)	−0.0060 (15)	0.0020 (14)	−0.0106 (15)
C85	0.0233 (18)	0.031 (2)	0.0223 (18)	0.0054 (15)	−0.0056 (14)	−0.0128 (15)
C86	0.0265 (18)	0.0194 (17)	0.0167 (16)	0.0017 (14)	−0.0038 (14)	−0.0069 (13)
C91	0.0238 (18)	0.0189 (17)	0.0172 (16)	−0.0020 (14)	0.0022 (13)	−0.0038 (13)
C92	0.0224 (17)	0.0175 (16)	0.0114 (15)	−0.0029 (13)	0.0004 (13)	−0.0018 (13)
C93	0.0223 (17)	0.0167 (16)	0.0172 (16)	−0.0028 (13)	0.0029 (13)	−0.0038 (13)
C94	0.0280 (19)	0.0214 (18)	0.0225 (18)	−0.0031 (15)	−0.0029 (15)	−0.0031 (14)
C95	0.029 (2)	0.027 (2)	0.029 (2)	0.0046 (16)	−0.0036 (16)	−0.0033 (16)
C96	0.041 (2)	0.0234 (19)	0.029 (2)	0.0087 (17)	−0.0001 (17)	−0.0090 (16)
C97	0.036 (2)	0.0250 (19)	0.0231 (18)	0.0021 (16)	0.0017 (16)	−0.0104 (15)
C98	0.0288 (19)	0.0241 (18)	0.0158 (17)	0.0010 (15)	−0.0055 (14)	−0.0076 (14)
C99	0.033 (2)	0.028 (2)	0.0226 (18)	−0.0034 (16)	−0.0010 (15)	−0.0111 (15)
C9A	0.039 (2)	0.050 (3)	0.041 (2)	−0.011 (2)	−0.0057 (19)	−0.021 (2)
Cl1	0.0284 (5)	0.0251 (5)	0.0350 (5)	−0.0003 (4)	−0.0011 (4)	−0.0131 (4)
O11	0.0493 (19)	0.0329 (17)	0.057 (2)	0.0112 (14)	0.0063 (15)	−0.0068 (15)
O12	0.089 (3)	0.061 (3)	0.132 (4)	0.028 (2)	0.065 (3)	0.019 (3)
O13	0.204 (7)	0.285 (9)	0.191 (7)	0.195 (7)	−0.161 (6)	−0.204 (7)
O14	0.047 (2)	0.037 (2)	0.303 (9)	−0.0066 (19)	0.040 (4)	−0.032 (4)
Cl2	0.0293 (5)	0.0249 (4)	0.0235 (4)	0.0016 (4)	−0.0026 (3)	−0.0102 (3)
O21	0.0386 (16)	0.0266 (15)	0.0529 (18)	0.0063 (12)	−0.0061 (13)	−0.0149 (13)
O22	0.069 (2)	0.058 (2)	0.0453 (19)	0.0239 (17)	−0.0256 (16)	−0.0379 (17)
O23	0.0318 (16)	0.0325 (16)	0.077 (2)	0.0047 (13)	−0.0049 (15)	−0.0085 (16)
O24	0.068 (2)	0.0460 (19)	0.0379 (17)	−0.0154 (17)	0.0133 (16)	−0.0106 (15)

Geometric parameters (Å, º) top

Cu1—N43	2.026 (3)	Cu2—N63	1.965 (3)
Cu1—N13	2.031 (3)	Cu2—N53	1.969 (3)
Cu1—N52	2.033 (4)	N53—C55	1.128 (5)
Cu1—N51	2.061 (4)	N61—C62	1.354 (4)
N11—C12	1.368 (4)	N61—C61	1.385 (4)
N11—C11	1.377 (5)	N61—C68	1.467 (5)
N11—C18	1.470 (5)	N63—C62	1.327 (4)
N13—C12	1.321 (5)	N63—C63	1.393 (4)
N13—C13	1.390 (4)	N91—C92	1.367 (4)
N41—C42	1.366 (4)	N91—C91	1.391 (4)
N41—C41	1.382 (4)	N91—C98	1.464 (4)
N41—C48	1.462 (4)	N93—C92	1.328 (4)
N43—C42	1.327 (4)	N93—C93	1.389 (4)
N43—C43	1.392 (4)	C55—C56	1.460 (5)
N51—C51	1.135 (6)	C56—H56A	0.9600
N52—C53	1.154 (6)	C56—H56B	0.9600
C11—C17	1.397 (5)	C56—H56C	0.9600
C11—C13	1.405 (5)	C61—C63	1.391 (5)
C12—C22	1.483 (5)	C61—C67	1.400 (5)
C13—C14	1.391 (5)	C62—C72	1.478 (5)
C14—C15	1.390 (6)	C63—C64	1.392 (5)
C14—H14	0.9300	C64—C65	1.383 (5)
C15—C16	1.393 (7)	C64—H64	0.9300
C15—H15	0.9300	C65—C66	1.402 (6)
C16—C17	1.382 (7)	C65—H65	0.9300
C16—H16	0.9300	C66—C67	1.373 (6)
C17—H17	0.9300	C66—H66	0.9300
C18—C19	1.533 (6)	C67—H67	0.9300
C18—H18A	0.9700	C68—C69	1.535 (6)
C18—H18B	0.9700	C68—H68A	0.9700
C19—C1A	1.508 (6)	C68—H68B	0.9700
C19—H19A	0.9700	C69—C6A	1.507 (7)
C19—H19B	0.9700	C69—H69A	0.9700
C1A—H1A1	0.9600	C69—H69B	0.9700
C1A—H1A2	0.9600	C6A—H6A1	0.9600
C1A—H1A3	0.9600	C6A—H6A2	0.9600
C21—C26	1.395 (5)	C6A—H6A3	0.9600
C21—C22	1.399 (5)	C71—C76	1.400 (5)
C21—C31	1.488 (5)	C71—C72	1.405 (5)
C22—C23	1.384 (5)	C71—C81	1.483 (5)
C23—C24	1.380 (6)	C72—C73	1.392 (5)
C23—H23	0.9300	C73—C74	1.379 (5)
C24—C25	1.381 (6)	C73—H73	0.9300
C24—H24	0.9300	C74—C75	1.387 (5)
C25—C26	1.382 (5)	C74—H74	0.9300
C25—H25	0.9300	C75—C76	1.390 (5)
C26—H26	0.9300	C75—H75	0.9300
C31—C36	1.398 (5)	C76—H76	0.9300
C31—C32	1.403 (5)	C81—C82	1.395 (5)
C32—C33	1.391 (5)	C81—C86	1.400 (5)
C32—C42	1.479 (5)	C82—C83	1.394 (5)
C33—C34	1.390 (5)	C82—C92	1.481 (5)
C33—H33	0.9300	C83—C84	1.378 (5)
C34—C35	1.385 (5)	C83—H83	0.9300
C34—H34	0.9300	C84—C85	1.392 (5)
C35—C36	1.383 (5)	C84—H84	0.9300
C35—H35	0.9300	C85—C86	1.382 (5)
C36—H36	0.9300	C85—H85	0.9300
C41—C43	1.391 (5)	C86—H86	0.9300
C41—C47	1.399 (5)	C91—C97	1.390 (5)
C43—C44	1.403 (5)	C91—C93	1.395 (5)
C44—C45	1.378 (5)	C93—C94	1.395 (5)
C44—H44	0.9300	C94—C95	1.376 (5)
C45—C46	1.400 (6)	C94—H94	0.9300
C45—H45	0.9300	C95—C96	1.393 (6)
C46—C47	1.378 (5)	C95—H95	0.9300
C46—H46	0.9300	C96—C97	1.374 (6)
C47—H47	0.9300	C96—H96	0.9300
C48—C49	1.524 (5)	C97—H97	0.9300
C48—H48A	0.9700	C98—C99	1.520 (5)
C48—H48B	0.9700	C98—H98A	0.9700
C49—C4A	1.518 (5)	C98—H98B	0.9700
C49—H49A	0.9700	C99—C9A	1.517 (5)
C49—H49B	0.9700	C99—H99A	0.9700
C4A—H4A1	0.9600	C99—H99B	0.9700
C4A—H4A2	0.9600	C9A—H9A1	0.9600
C4A—H4A3	0.9600	C9A—H9A2	0.9600
C51—C52	1.468 (7)	C9A—H9A3	0.9600
C52—H52A	0.9600	Cl1—O13	1.363 (4)
C52—H52B	0.9600	Cl1—O14	1.376 (4)
C52—H52C	0.9600	Cl1—O12	1.396 (3)
C53—C54	1.464 (6)	Cl1—O11	1.413 (3)
C54—H54A	0.9600	Cl2—O24	1.412 (3)
C54—H54B	0.9600	Cl2—O23	1.425 (3)
C54—H54C	0.9600	Cl2—O22	1.431 (3)
Cu2—N93	1.944 (3)	Cl2—O21	1.436 (3)

N43—Cu1—N13	121.78 (11)	N93—Cu2—N53	121.74 (12)
N43—Cu1—N52	109.74 (14)	N63—Cu2—N53	108.74 (12)
N13—Cu1—N52	108.01 (13)	C55—N53—Cu2	164.1 (3)
N43—Cu1—N51	97.69 (16)	C62—N61—C61	106.8 (3)
N13—Cu1—N51	108.88 (13)	C62—N61—C68	127.7 (3)
N52—Cu1—N51	110.1 (2)	C61—N61—C68	125.5 (3)
C12—N11—C11	107.1 (3)	C62—N63—C63	105.7 (3)
C12—N11—C18	127.5 (3)	C62—N63—Cu2	121.4 (2)
C11—N11—C18	125.4 (3)	C63—N63—Cu2	132.6 (2)
C12—N13—C13	105.7 (3)	C92—N91—C91	106.9 (3)
C12—N13—Cu1	129.8 (2)	C92—N91—C98	128.9 (3)
C13—N13—Cu1	124.5 (2)	C91—N91—C98	124.2 (3)
C42—N41—C41	107.2 (3)	C92—N93—C93	105.9 (3)
C42—N41—C48	127.9 (3)	C92—N93—Cu2	128.9 (2)
C41—N41—C48	124.9 (3)	C93—N93—Cu2	125.2 (2)
C42—N43—C43	105.3 (3)	N53—C55—C56	178.5 (5)
C42—N43—Cu1	127.6 (2)	C55—C56—H56A	109.5
C43—N43—Cu1	126.9 (2)	C55—C56—H56B	109.5
C51—N51—Cu1	161.8 (5)	H56A—C56—H56B	109.5
C53—N52—Cu1	170.2 (5)	C55—C56—H56C	109.5
N11—C11—C17	131.8 (4)	H56A—C56—H56C	109.5
N11—C11—C13	105.8 (3)	H56B—C56—H56C	109.5
C17—C11—C13	122.4 (4)	N61—C61—C63	106.4 (3)
N13—C12—N11	112.3 (3)	N61—C61—C67	131.9 (3)
N13—C12—C22	125.6 (3)	C63—C61—C67	121.7 (3)
N11—C12—C22	122.1 (3)	N63—C62—N61	112.4 (3)
N13—C13—C14	130.6 (3)	N63—C62—C72	121.5 (3)
N13—C13—C11	109.1 (3)	N61—C62—C72	126.0 (3)
C14—C13—C11	120.3 (3)	C61—C63—C64	121.3 (3)
C15—C14—C13	117.1 (4)	C61—C63—N63	108.7 (3)
C15—C14—H14	121.5	C64—C63—N63	129.9 (3)
C13—C14—H14	121.5	C65—C64—C63	117.2 (3)
C14—C15—C16	122.1 (4)	C65—C64—H64	121.4
C14—C15—H15	118.9	C63—C64—H64	121.4
C16—C15—H15	118.9	C64—C65—C66	120.9 (3)
C17—C16—C15	121.6 (4)	C64—C65—H65	119.5
C17—C16—H16	119.2	C66—C65—H65	119.5
C15—C16—H16	119.2	C67—C66—C65	122.5 (3)
C16—C17—C11	116.4 (4)	C67—C66—H66	118.7
C16—C17—H17	121.8	C65—C66—H66	118.7
C11—C17—H17	121.8	C66—C67—C61	116.3 (4)
N11—C18—C19	111.4 (3)	C66—C67—H67	121.8
N11—C18—H18A	109.3	C61—C67—H67	121.8
C19—C18—H18A	109.3	N61—C68—C69	113.0 (3)
N11—C18—H18B	109.3	N61—C68—H68A	109.0
C19—C18—H18B	109.3	C69—C68—H68A	109.0
H18A—C18—H18B	108.0	N61—C68—H68B	109.0
C1A—C19—C18	112.1 (4)	C69—C68—H68B	109.0
C1A—C19—H19A	109.2	H68A—C68—H68B	107.8
C18—C19—H19A	109.2	C6A—C69—C68	111.3 (4)
C1A—C19—H19B	109.2	C6A—C69—H69A	109.4
C18—C19—H19B	109.2	C68—C69—H69A	109.4
H19A—C19—H19B	107.9	C6A—C69—H69B	109.4
C19—C1A—H1A1	109.5	C68—C69—H69B	109.4
C19—C1A—H1A2	109.5	H69A—C69—H69B	108.0
H1A1—C1A—H1A2	109.5	C69—C6A—H6A1	109.5
C19—C1A—H1A3	109.5	C69—C6A—H6A2	109.5
H1A1—C1A—H1A3	109.5	H6A1—C6A—H6A2	109.5
H1A2—C1A—H1A3	109.5	C69—C6A—H6A3	109.5
C26—C21—C22	118.8 (3)	H6A1—C6A—H6A3	109.5
C26—C21—C31	119.0 (3)	H6A2—C6A—H6A3	109.5
C22—C21—C31	122.2 (3)	C76—C71—C72	118.9 (3)
C23—C22—C21	119.9 (3)	C76—C71—C81	120.2 (3)
C23—C22—C12	120.6 (3)	C72—C71—C81	120.7 (3)
C21—C22—C12	119.4 (3)	C73—C72—C71	119.8 (3)
C24—C23—C22	120.7 (3)	C73—C72—C62	121.4 (3)
C24—C23—H23	119.7	C71—C72—C62	118.6 (3)
C22—C23—H23	119.7	C74—C73—C72	120.6 (3)
C23—C24—C25	119.8 (4)	C74—C73—H73	119.7
C23—C24—H24	120.1	C72—C73—H73	119.7
C25—C24—H24	120.1	C73—C74—C75	120.1 (3)
C24—C25—C26	120.1 (3)	C73—C74—H74	119.9
C24—C25—H25	120.0	C75—C74—H74	119.9
C26—C25—H25	120.0	C74—C75—C76	120.0 (3)
C25—C26—C21	120.7 (3)	C74—C75—H75	120.0
C25—C26—H26	119.7	C76—C75—H75	120.0
C21—C26—H26	119.7	C75—C76—C71	120.4 (3)
C36—C31—C32	119.2 (3)	C75—C76—H76	119.8
C36—C31—C21	119.5 (3)	C71—C76—H76	119.8
C32—C31—C21	121.1 (3)	C82—C81—C86	118.6 (3)
C33—C32—C31	119.6 (3)	C82—C81—C71	123.7 (3)
C33—C32—C42	120.3 (3)	C86—C81—C71	117.6 (3)
C31—C32—C42	120.0 (3)	C83—C82—C81	119.8 (3)
C34—C33—C32	120.5 (3)	C83—C82—C92	119.4 (3)
C34—C33—H33	119.7	C81—C82—C92	120.7 (3)
C32—C33—H33	119.7	C84—C83—C82	120.7 (3)
C35—C34—C33	119.9 (3)	C84—C83—H83	119.6
C35—C34—H34	120.1	C82—C83—H83	119.6
C33—C34—H34	120.1	C83—C84—C85	120.1 (3)
C36—C35—C34	120.1 (3)	C83—C84—H84	120.0
C36—C35—H35	120.0	C85—C84—H84	120.0
C34—C35—H35	120.0	C86—C85—C84	119.3 (3)
C35—C36—C31	120.6 (3)	C86—C85—H85	120.3
C35—C36—H36	119.7	C84—C85—H85	120.3
C31—C36—H36	119.7	C85—C86—C81	121.4 (3)
N41—C41—C43	105.7 (3)	C85—C86—H86	119.3
N41—C41—C47	131.5 (3)	C81—C86—H86	119.3
C43—C41—C47	122.8 (3)	C97—C91—N91	131.7 (3)
N43—C42—N41	112.1 (3)	C97—C91—C93	122.5 (3)
N43—C42—C32	124.3 (3)	N91—C91—C93	105.8 (3)
N41—C42—C32	123.5 (3)	N93—C92—N91	112.0 (3)
C41—C43—N43	109.7 (3)	N93—C92—C82	124.7 (3)
C41—C43—C44	119.9 (3)	N91—C92—C82	123.3 (3)
N43—C43—C44	130.4 (3)	N93—C93—C94	130.4 (3)
C45—C44—C43	117.4 (3)	N93—C93—C91	109.4 (3)
C45—C44—H44	121.3	C94—C93—C91	120.2 (3)
C43—C44—H44	121.3	C95—C94—C93	117.5 (3)
C44—C45—C46	121.9 (3)	C95—C94—H94	121.2
C44—C45—H45	119.0	C93—C94—H94	121.2
C46—C45—H45	119.0	C94—C95—C96	121.3 (4)
C47—C46—C45	121.6 (3)	C94—C95—H95	119.4
C47—C46—H46	119.2	C96—C95—H95	119.4
C45—C46—H46	119.2	C97—C96—C95	122.4 (3)
C46—C47—C41	116.3 (3)	C97—C96—H96	118.8
C46—C47—H47	121.9	C95—C96—H96	118.8
C41—C47—H47	121.9	C96—C97—C91	116.0 (3)
N41—C48—C49	113.1 (3)	C96—C97—H97	122.0
N41—C48—H48A	109.0	C91—C97—H97	122.0
C49—C48—H48A	109.0	N91—C98—C99	112.8 (3)
N41—C48—H48B	109.0	N91—C98—H98A	109.0
C49—C48—H48B	109.0	C99—C98—H98A	109.0
H48A—C48—H48B	107.8	N91—C98—H98B	109.0
C4A—C49—C48	111.0 (3)	C99—C98—H98B	109.0
C4A—C49—H49A	109.4	H98A—C98—H98B	107.8
C48—C49—H49A	109.4	C9A—C99—C98	111.3 (3)
C4A—C49—H49B	109.4	C9A—C99—H99A	109.4
C48—C49—H49B	109.4	C98—C99—H99A	109.4
H49A—C49—H49B	108.0	C9A—C99—H99B	109.4
C49—C4A—H4A1	109.5	C98—C99—H99B	109.4
C49—C4A—H4A2	109.5	H99A—C99—H99B	108.0
H4A1—C4A—H4A2	109.5	C99—C9A—H9A1	109.5
C49—C4A—H4A3	109.5	C99—C9A—H9A2	109.5
H4A1—C4A—H4A3	109.5	H9A1—C9A—H9A2	109.5
H4A2—C4A—H4A3	109.5	C99—C9A—H9A3	109.5
N51—C51—C52	178.8 (7)	H9A1—C9A—H9A3	109.5
C51—C52—H52A	109.5	H9A2—C9A—H9A3	109.5
C51—C52—H52B	109.5	O13—Cl1—O14	109.7 (6)
H52A—C52—H52B	109.5	O13—Cl1—O12	107.5 (5)
C51—C52—H52C	109.5	O14—Cl1—O12	107.8 (3)
H52A—C52—H52C	109.5	O13—Cl1—O11	109.0 (3)
H52B—C52—H52C	109.5	O14—Cl1—O11	109.7 (3)
N52—C53—C54	177.9 (7)	O12—Cl1—O11	113.2 (2)
C53—C54—H54A	109.5	O24—Cl2—O23	109.1 (2)
C53—C54—H54B	109.5	O24—Cl2—O22	109.1 (2)
H54A—C54—H54B	109.5	O23—Cl2—O22	109.6 (2)
C53—C54—H54C	109.5	O24—Cl2—O21	110.0 (2)
H54A—C54—H54C	109.5	O23—Cl2—O21	109.47 (18)
H54B—C54—H54C	109.5	O22—Cl2—O21	109.63 (19)
N93—Cu2—N63	128.26 (11)

N43—Cu1—N13—C12	27.1 (3)	C41—N41—C48—C49	−75.9 (4)
N52—Cu1—N13—C12	−101.1 (3)	N41—C48—C49—C4A	178.7 (3)
N51—Cu1—N13—C12	139.4 (3)	N93—Cu2—N53—C55	−109.1 (11)
N43—Cu1—N13—C13	−151.8 (2)	N63—Cu2—N53—C55	59.1 (11)
N52—Cu1—N13—C13	80.0 (3)	N93—Cu2—N63—C62	61.9 (3)
N51—Cu1—N13—C13	−39.6 (3)	N53—Cu2—N63—C62	−105.3 (3)
N13—Cu1—N43—C42	40.8 (3)	N93—Cu2—N63—C63	−125.6 (3)
N52—Cu1—N43—C42	168.3 (3)	N53—Cu2—N63—C63	67.2 (3)
N51—Cu1—N43—C42	−77.1 (3)	N63—Cu2—N93—C92	8.9 (3)
N13—Cu1—N43—C43	−143.4 (3)	N53—Cu2—N93—C92	174.7 (3)
N52—Cu1—N43—C43	−15.9 (3)	N63—Cu2—N93—C93	−171.1 (2)
N51—Cu1—N43—C43	98.7 (3)	N53—Cu2—N93—C93	−5.4 (3)
N43—Cu1—N51—C51	10.0 (13)	C62—N61—C61—C63	−1.3 (4)
N13—Cu1—N51—C51	−117.4 (12)	C68—N61—C61—C63	−177.7 (3)
N52—Cu1—N51—C51	124.4 (12)	C62—N61—C61—C67	177.7 (4)
C12—N11—C11—C17	178.3 (4)	C68—N61—C61—C67	1.3 (6)
C18—N11—C11—C17	−2.7 (6)	C63—N63—C62—N61	0.0 (4)
C12—N11—C11—C13	−0.6 (4)	Cu2—N63—C62—N61	174.3 (2)
C18—N11—C11—C13	178.5 (3)	C63—N63—C62—C72	179.5 (3)
C13—N13—C12—N11	0.9 (4)	Cu2—N63—C62—C72	−6.3 (4)
Cu1—N13—C12—N11	−178.2 (2)	C61—N61—C62—N63	0.8 (4)
C13—N13—C12—C22	−179.4 (3)	C68—N61—C62—N63	177.1 (3)
Cu1—N13—C12—C22	1.5 (5)	C61—N61—C62—C72	−178.6 (3)
C11—N11—C12—N13	−0.2 (4)	C68—N61—C62—C72	−2.3 (6)
C18—N11—C12—N13	−179.2 (3)	N61—C61—C63—C64	−179.0 (3)
C11—N11—C12—C22	−179.9 (3)	C67—C61—C63—C64	1.9 (5)
C18—N11—C12—C22	1.1 (5)	N61—C61—C63—N63	1.3 (4)
C12—N13—C13—C14	179.0 (4)	C67—C61—C63—N63	−177.8 (3)
Cu1—N13—C13—C14	−1.8 (5)	C62—N63—C63—C61	−0.9 (4)
C12—N13—C13—C11	−1.3 (4)	Cu2—N63—C63—C61	−174.2 (2)
Cu1—N13—C13—C11	177.9 (2)	C62—N63—C63—C64	179.5 (4)
N11—C11—C13—N13	1.1 (4)	Cu2—N63—C63—C64	6.2 (6)
C17—C11—C13—N13	−177.9 (3)	C61—C63—C64—C65	−0.5 (5)
N11—C11—C13—C14	−179.1 (3)	N63—C63—C64—C65	179.1 (3)
C17—C11—C13—C14	1.9 (5)	C63—C64—C65—C66	−0.5 (5)
N13—C13—C14—C15	178.4 (3)	C64—C65—C66—C67	0.1 (6)
C11—C13—C14—C15	−1.3 (5)	C65—C66—C67—C61	1.2 (6)
C13—C14—C15—C16	0.2 (6)	N61—C61—C67—C66	179.0 (4)
C14—C15—C16—C17	0.4 (6)	C63—C61—C67—C66	−2.2 (5)
C15—C16—C17—C11	0.1 (6)	C62—N61—C68—C69	107.9 (4)
N11—C11—C17—C16	−179.9 (4)	C61—N61—C68—C69	−76.4 (5)
C13—C11—C17—C16	−1.2 (6)	N61—C68—C69—C6A	176.0 (4)
C12—N11—C18—C19	101.2 (4)	C76—C71—C72—C73	−1.6 (5)
C11—N11—C18—C19	−77.7 (5)	C81—C71—C72—C73	173.8 (3)
N11—C18—C19—C1A	176.9 (4)	C76—C71—C72—C62	172.8 (3)
C26—C21—C22—C23	−1.0 (5)	C81—C71—C72—C62	−11.7 (5)
C31—C21—C22—C23	175.5 (3)	N63—C62—C72—C73	110.0 (4)
C26—C21—C22—C12	178.2 (3)	N61—C62—C72—C73	−70.6 (5)
C31—C21—C22—C12	−5.3 (5)	N63—C62—C72—C71	−64.4 (4)
N13—C12—C22—C23	111.3 (4)	N61—C62—C72—C71	115.0 (4)
N11—C12—C22—C23	−69.0 (4)	C71—C72—C73—C74	1.0 (5)
N13—C12—C22—C21	−67.8 (5)	C62—C72—C73—C74	−173.3 (3)
N11—C12—C22—C21	111.9 (4)	C72—C73—C74—C75	0.7 (6)
C21—C22—C23—C24	−1.1 (5)	C73—C74—C75—C76	−1.8 (6)
C12—C22—C23—C24	179.7 (3)	C74—C75—C76—C71	1.1 (5)
C22—C23—C24—C25	1.7 (5)	C72—C71—C76—C75	0.6 (5)
C23—C24—C25—C26	−0.1 (5)	C81—C71—C76—C75	−174.9 (3)
C24—C25—C26—C21	−2.0 (5)	C76—C71—C81—C82	−64.1 (4)
C22—C21—C26—C25	2.6 (5)	C72—C71—C81—C82	120.5 (4)
C31—C21—C26—C25	−174.1 (3)	C76—C71—C81—C86	113.7 (4)
C26—C21—C31—C36	106.4 (4)	C72—C71—C81—C86	−61.7 (4)
C22—C21—C31—C36	−70.1 (4)	C86—C81—C82—C83	−1.9 (5)
C26—C21—C31—C32	−68.1 (4)	C71—C81—C82—C83	175.9 (3)
C22—C21—C31—C32	115.5 (4)	C86—C81—C82—C92	174.7 (3)
C36—C31—C32—C33	−2.2 (5)	C71—C81—C82—C92	−7.5 (5)
C21—C31—C32—C33	172.3 (3)	C81—C82—C83—C84	0.2 (5)
C36—C31—C32—C42	176.3 (3)	C92—C82—C83—C84	−176.4 (3)
C21—C31—C32—C42	−9.3 (5)	C82—C83—C84—C85	1.4 (5)
C31—C32—C33—C34	0.7 (5)	C83—C84—C85—C86	−1.3 (5)
C42—C32—C33—C34	−177.8 (3)	C84—C85—C86—C81	−0.5 (5)
C32—C33—C34—C35	1.5 (5)	C82—C81—C86—C85	2.1 (5)
C33—C34—C35—C36	−2.1 (5)	C71—C81—C86—C85	−175.9 (3)
C34—C35—C36—C31	0.6 (5)	C92—N91—C91—C97	−177.9 (4)
C32—C31—C36—C35	1.5 (5)	C98—N91—C91—C97	1.2 (6)
C21—C31—C36—C35	−173.0 (3)	C92—N91—C91—C93	0.0 (3)
C42—N41—C41—C43	−0.6 (4)	C98—N91—C91—C93	179.1 (3)
C48—N41—C41—C43	179.0 (3)	C93—N93—C92—N91	0.6 (4)
C42—N41—C41—C47	178.7 (4)	Cu2—N93—C92—N91	−179.4 (2)
C48—N41—C41—C47	−1.7 (6)	C93—N93—C92—C82	−177.6 (3)
C43—N43—C42—N41	1.1 (4)	Cu2—N93—C92—C82	2.4 (5)
Cu1—N43—C42—N41	177.6 (2)	C91—N91—C92—N93	−0.4 (4)
C43—N43—C42—C32	−178.0 (3)	C98—N91—C92—N93	−179.4 (3)
Cu1—N43—C42—C32	−1.5 (5)	C91—N91—C92—C82	177.8 (3)
C41—N41—C42—N43	−0.3 (4)	C98—N91—C92—C82	−1.2 (5)
C48—N41—C42—N43	−179.8 (3)	C83—C82—C92—N93	118.2 (4)
C41—N41—C42—C32	178.8 (3)	C81—C82—C92—N93	−58.4 (4)
C48—N41—C42—C32	−0.8 (5)	C83—C82—C92—N91	−59.8 (4)
C33—C32—C42—N43	110.4 (4)	C81—C82—C92—N91	123.6 (3)
C31—C32—C42—N43	−68.1 (4)	C92—N93—C93—C94	177.8 (3)
C33—C32—C42—N41	−68.6 (4)	Cu2—N93—C93—C94	−2.2 (5)
C31—C32—C42—N41	113.0 (4)	C92—N93—C93—C91	−0.6 (4)
N41—C41—C43—N43	1.3 (4)	Cu2—N93—C93—C91	179.5 (2)
C47—C41—C43—N43	−178.1 (3)	C97—C91—C93—N93	178.5 (3)
N41—C41—C43—C44	−177.2 (3)	N91—C91—C93—N93	0.3 (4)
C47—C41—C43—C44	3.4 (5)	C97—C91—C93—C94	−0.1 (5)
C42—N43—C43—C41	−1.4 (4)	N91—C91—C93—C94	−178.2 (3)
Cu1—N43—C43—C41	−178.0 (2)	N93—C93—C94—C95	−177.8 (3)
C42—N43—C43—C44	176.8 (4)	C91—C93—C94—C95	0.4 (5)
Cu1—N43—C43—C44	0.3 (5)	C93—C94—C95—C96	−0.3 (5)
C41—C43—C44—C45	−2.1 (5)	C94—C95—C96—C97	0.0 (6)
N43—C43—C44—C45	179.8 (4)	C95—C96—C97—C91	0.3 (6)
C43—C44—C45—C46	−0.7 (6)	N91—C91—C97—C96	177.3 (4)
C44—C45—C46—C47	2.5 (6)	C93—C91—C97—C96	−0.3 (5)
C45—C46—C47—C41	−1.3 (6)	C92—N91—C98—C99	105.0 (4)
N41—C41—C47—C46	179.1 (4)	C91—N91—C98—C99	−73.9 (4)
C43—C41—C47—C46	−1.6 (5)	N91—C98—C99—C9A	176.3 (3)
C42—N41—C48—C49	103.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···O14ⁱ	0.97	2.54	3.461 (7)	158
C26—H26···O14ⁱⁱ	0.93	2.53	3.308 (7)	142
C34—H34···O14ⁱⁱⁱ	0.93	2.55	3.337 (6)	143
C54—H54A···O23^iv	0.96	2.58	3.272 (6)	129
C54—H54B···O22	0.96	2.51	3.039 (7)	115
C56—H56B···O11^v	0.96	2.35	3.283 (5)	165
C68—H68B···O22	0.97	2.44	3.320 (6)	151
C86—H86···O21	0.93	2.58	3.279 (5)	132
C97—H97···O24^vi	0.93	2.50	3.425 (5)	174
C98—H98B···O21^vi	0.97	2.54	3.503 (5)	174

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

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		SGML
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A structure with trigonally and tetra­hedrally coordinated CuI cations: rac-(acetonitrile)[2,2′-bis­(1-propyl-1H-benzimidazol-2-yl)biphenyl]copper(I) bis­(acetonitrile)[2,2′-bis­(1-propyl-1H-benzimidazol-2-yl)biphenyl]copper(I) bis­(perchlorate)

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A structure with trigonally and tetrahedrally coordinated Cu^I cations: rac-(acetonitrile)[2,2′-bis(1-propyl-1H-benzimidazol-2-yl)biphenyl]copper(I) bis(acetonitrile)[2,2′-bis(1-propyl-1H-benzimidazol-2-yl)biphenyl]copper(I) bis(perchlorate)