Crystal structure of hexa-μ-chlorido-μ₄-oxido-tetra­kis­{[1-(2-hy­droxy­eth­yl)-2-methyl-5-nitro-1H-imidazole-κN³]copper(II)} containing short NO₂...NO₂ contacts

The title tetra­nuclear cluster contains a tetra­hedral arrangement of copper(II) ions bonded to a central oxygen atom. The extended structure shows short O...N inter­actions between the nitro groups of adjacent clusters, which are oriented perpendicular to each other in a manner that has previously been described as an O_NO2...π(N)_NO2 inter­action.

Key indicators

• Single-crystal X-ray study
• T = 130 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.045
• wR factor = 0.118
• Data-to-parameter ratio = 25.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Non-Solvent  Resd 1  O   Ueq(max)/Ueq(min) Range        6.3 Ratio
PLAT417_ALERT_2_B Short Inter D-H..H-D       H31A     ..H41A     .       2.09 Ang.
                                             -1/2+x,1/2+y,z  =      3_455 Check
PLAT420_ALERT_2_B D-H Without Acceptor       O11      --H11A     .     Please Check
PLAT420_ALERT_2_B D-H Without Acceptor       O21      --H21A     .     Please Check
PLAT420_ALERT_2_B D-H Without Acceptor       O31      --H31A     .     Please Check
PLAT430_ALERT_2_B Short Inter D...A Contact  O12      ..N33      .       2.78 Ang.
                                             1/2+x,-1/2+y,z  =      3_545 Check

Alert level C
PLAT213_ALERT_2_C Atom O12             has ADP max/min Ratio .....        3.6 prolat
PLAT213_ALERT_2_C Atom O13             has ADP max/min Ratio .....        3.3 prolat
PLAT222_ALERT_3_C Non-Solv.  Resd 1  H   Uiso(max)/Uiso(min) Range        4.4 Ratio
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        Cl6 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        N13 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        N43 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C25 Check
PLAT415_ALERT_2_C Short Inter D-H..H-X       H41A     ..H35E     .       2.10 Ang.
                                             1/2+x,-1/2+y,z  =      3_545 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
PLAT976_ALERT_2_C Check Calcd Resid. Dens.  0.89A   From O22            -0.52 eA-3
PLAT976_ALERT_2_C Check Calcd Resid. Dens.  0.78A   From O21            -0.48 eA-3

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         17 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          6 Report
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large      31.44 Why ?
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT173_ALERT_4_G The CIF-Embedded .res File Contains DANG Records          1 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records          1 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )         5% Note
PLAT432_ALERT_2_G Short Inter X...Y Contact  O13      ..C41              2.93 Ang.
                                              1/2+x,1/2+y,z  =      3_555 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O32      ..C11              3.00 Ang.
                                            3/2-x,1/2-y,1-z  =      7_656 Check
PLAT605_ALERT_4_G Largest Solvent Accessible VOID in the Structure        387 A   3  
PLAT794_ALERT_5_G Tentative Bond Valency for Cu1       (II)      .       2.08 Info
PLAT794_ALERT_5_G Tentative Bond Valency for Cu2       (II)      .       2.17 Info
PLAT794_ALERT_5_G Tentative Bond Valency for Cu3       (II)      .       2.11 Info
PLAT794_ALERT_5_G Tentative Bond Valency for Cu4       (II)      .       2.03 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        120 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         50 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   6 ALERT level B = A potentially serious problem, consider carefully
  11 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  21 ALERT level G = General information/check it is not something unexpected

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

---

Computing details

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Hexa-µ-chlorido-µ₄-oxido-tetrakis{[1-(2-hydroxyethyl)-2-methyl-5-nitro-1H-imidazole-κN³]copper(II)}

Crystal data

[Cu4Cl6O(C6H9N3O3)4]	F(000) = 4688
Mr = 1167.51	Dx = 1.613 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 22.125 (3) Å	Cell parameters from 9836 reflections
b = 13.361 (2) Å	θ = 2.2–29.8°
c = 32.633 (5) Å	µ = 2.14 mm^−1
β = 94.752 (2)°	T = 130 K
V = 9613 (3) Å^3	Plate, gold
Z = 8	0.36 × 0.20 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer	11100 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.048
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θmax = 30.8°, θmin = 1.3°
Tmin = 0.586, Tmax = 0.746	h = −31→31
78050 measured reflections	k = −19→19
15003 independent reflections	l = −46→46

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.0497P)^2 + 31.4385P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.002
15003 reflections	Δρmax = 1.55 e Å^−3
579 parameters	Δρmin = −1.09 e Å^−3
120 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.80290 (2)	−0.01300 (3)	0.39169 (2)	0.02214 (8)
Cu2	0.70660 (2)	−0.01915 (3)	0.31768 (2)	0.02614 (8)
Cu3	0.66594 (2)	0.02107 (3)	0.40449 (2)	0.03036 (9)
Cu4	0.71326 (2)	−0.19124 (3)	0.38380 (2)	0.02342 (8)
Cl1	0.81567 (3)	−0.18214 (5)	0.41707 (2)	0.02840 (14)
Cl2	0.81362 (3)	−0.00755 (7)	0.31780 (2)	0.03451 (17)
Cl3	0.75591 (3)	0.09683 (6)	0.43943 (2)	0.03046 (16)
Cl4	0.67511 (3)	−0.19355 (6)	0.31175 (2)	0.03082 (15)
Cl5	0.63812 (3)	−0.13927 (7)	0.42920 (2)	0.03596 (17)
Cl6	0.63258 (5)	0.09252 (9)	0.33861 (3)	0.0547 (3)
N11	0.88549 (10)	0.03600 (18)	0.40341 (7)	0.0233 (5)
N12	0.96498 (10)	0.13435 (19)	0.39975 (9)	0.0302 (5)
N13	1.04472 (14)	0.0232 (3)	0.43287 (15)	0.0646 (12)
N21	0.68926 (12)	0.0204 (2)	0.26024 (8)	0.0307 (5)
N22	0.67466 (12)	0.1147 (2)	0.20463 (8)	0.0312 (6)
N23	0.62700 (16)	−0.0128 (3)	0.15652 (10)	0.0497 (9)
N31	0.60566 (11)	0.0980 (2)	0.43173 (8)	0.0316 (6)
N32	0.51725 (10)	0.15805 (18)	0.44639 (7)	0.0243 (5)
N33	0.55277 (14)	0.2806 (3)	0.50054 (11)	0.0513 (9)
N41	0.70835 (10)	−0.33784 (19)	0.38980 (7)	0.0254 (5)
N42	0.71449 (13)	−0.4914 (2)	0.41434 (9)	0.0355 (6)
N43	0.71274 (19)	−0.5839 (3)	0.34682 (11)	0.0591 (10)
O1	0.72212 (8)	−0.05076 (15)	0.37460 (6)	0.0222 (4)
O11	0.9926 (2)	0.1888 (4)	0.31860 (12)	0.0965 (15)
H11A	0.991 (3)	0.228 (4)	0.2983 (14)	0.145*
O12	1.05456 (14)	−0.0584 (3)	0.44694 (19)	0.125 (2)
O13	1.08424 (12)	0.0857 (3)	0.43043 (14)	0.0822 (12)
O21	0.55815 (16)	0.1846 (3)	0.17440 (17)	0.0943 (14)
H21A	0.5252 (8)	0.206 (4)	0.1839 (17)	0.141*
O22	0.59231 (17)	−0.0862 (2)	0.15657 (10)	0.0714 (11)
O23	0.64160 (13)	0.0312 (3)	0.12553 (8)	0.0606 (9)
O32	0.59897 (13)	0.3128 (3)	0.52030 (10)	0.0717 (11)
O33	0.50093 (13)	0.3067 (3)	0.50600 (10)	0.0683 (10)
O41	0.81469 (16)	−0.5364 (3)	0.47601 (15)	0.0891 (14)
H41A	0.8525 (9)	−0.5590 (19)	0.479 (2)	0.134*
O42	0.70514 (17)	−0.5744 (2)	0.30998 (9)	0.0643 (9)
O43	0.7238 (3)	−0.6628 (3)	0.36399 (13)	0.139 (2)
C11	0.90440 (12)	0.1254 (2)	0.39148 (9)	0.0261 (6)
C12	0.93477 (13)	−0.0145 (2)	0.42001 (11)	0.0333 (7)
H12A	0.9349	−0.0801	0.4312	0.040*
C13	0.98391 (13)	0.0457 (3)	0.41783 (12)	0.0380 (8)
C14	1.00057 (14)	0.2241 (3)	0.39029 (12)	0.0403 (8)
H14A	1.0302	0.2388	0.4139	0.048*
H14B	0.9729	0.2822	0.3864	0.048*
C15	1.03387 (19)	0.2108 (4)	0.35240 (16)	0.0627 (13)
H15A	1.0563	0.2729	0.3469	0.075*
H15B	1.0636	0.1557	0.3567	0.075*
C16	0.86509 (14)	0.2053 (3)	0.37248 (12)	0.0369 (7)
H16A	0.8229	0.1822	0.3698	0.055*
H16B	0.8780	0.2213	0.3452	0.055*
H16C	0.8684	0.2652	0.3899	0.055*
C21	0.69669 (14)	0.1114 (3)	0.24465 (9)	0.0311 (6)
C22	0.66075 (16)	−0.0364 (3)	0.22997 (11)	0.0382 (8)
H22A	0.6493	−0.1046	0.2323	0.046*
C23	0.65153 (15)	0.0209 (3)	0.19587 (10)	0.0355 (7)
C24	0.66535 (15)	0.2064 (3)	0.18002 (11)	0.0398 (8)
H24A	0.6692	0.1905	0.1507	0.048*
H24B	0.6972	0.2557	0.1889	0.048*
C25	0.60375 (18)	0.2517 (3)	0.18455 (15)	0.0514 (10)
H25A	0.6014	0.2739	0.2133	0.062*
H25B	0.5983	0.3113	0.1666	0.062*
C26	0.7245 (2)	0.1984 (3)	0.26728 (12)	0.0515 (10)
H26A	0.7510	0.1746	0.2908	0.077*
H26B	0.6925	0.2407	0.2771	0.077*
H26C	0.7483	0.2373	0.2489	0.077*
C31	0.54558 (12)	0.0912 (2)	0.42365 (9)	0.0247 (5)
C32	0.61649 (13)	0.1716 (2)	0.46056 (9)	0.0299 (6)
H32A	0.6552	0.1934	0.4719	0.036*
C33	0.56247 (14)	0.2077 (2)	0.47002 (10)	0.0308 (6)
C34	0.4518 (4)	0.1791 (10)	0.4409 (4)	0.027 (2)	0.515 (19)
H34A	0.4346	0.1503	0.4145	0.033*	0.515 (19)
H34B	0.4451	0.2523	0.4399	0.033*	0.515 (19)
C35	0.4205 (4)	0.1352 (8)	0.4754 (3)	0.034 (2)	0.515 (19)
H35A	0.4351	0.1686	0.5014	0.041*	0.515 (19)
H35B	0.3763	0.1469	0.4706	0.041*	0.515 (19)
O31	0.4317 (4)	0.0314 (7)	0.4788 (3)	0.040 (2)	0.515 (19)
H31A	0.4316 (19)	0.012 (3)	0.5031 (8)	0.060*	0.515 (19)
C34A	0.4496 (4)	0.1552 (12)	0.4507 (5)	0.036 (3)	0.485 (19)
H34D	0.4353	0.2234	0.4568	0.044*	0.485 (19)
H34E	0.4283	0.1335	0.4243	0.044*	0.485 (19)
C35A	0.4336 (5)	0.0858 (14)	0.4841 (4)	0.053 (4)	0.485 (19)
H35D	0.4523	0.1103	0.5108	0.063*	0.485 (19)
H35E	0.3890	0.0857	0.4854	0.063*	0.485 (19)
O31A	0.4535 (6)	−0.0129 (10)	0.4775 (2)	0.054 (3)	0.485 (19)
H31D	0.483 (6)	−0.012 (11)	0.489 (4)	0.081*	0.485 (19)
C36	0.51388 (13)	0.0216 (3)	0.39382 (11)	0.0357 (7)
H36A	0.5428	−0.0279	0.3850	0.053*
H36B	0.4966	0.0594	0.3699	0.053*
H36C	0.4813	−0.0126	0.4068	0.053*
C41	0.71482 (13)	−0.3938 (2)	0.42409 (9)	0.0287 (6)
C42	0.70446 (13)	−0.4025 (2)	0.35718 (9)	0.0281 (6)
H42A	0.6992	−0.3840	0.3290	0.034*
C43	0.70926 (16)	−0.4966 (2)	0.37164 (10)	0.0352 (7)
C44	0.71595 (19)	−0.5751 (3)	0.44430 (12)	0.0480 (9)
H44A	0.7000	−0.5519	0.4701	0.058*
H44B	0.6897	−0.6302	0.4330	0.058*
C45	0.7785 (2)	−0.6121 (4)	0.45304 (15)	0.0602 (11)
H45A	0.7781	−0.6746	0.4693	0.072*
H45B	0.7964	−0.6269	0.4269	0.072*
C46	0.71969 (17)	−0.3551 (3)	0.46674 (10)	0.0393 (8)
H46A	0.7583	−0.3765	0.4809	0.059*
H46B	0.6861	−0.3813	0.4813	0.059*
H46C	0.7179	−0.2818	0.4662	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.01369 (14)	0.02604 (17)	0.02712 (17)	−0.00543 (12)	0.00426 (12)	−0.00550 (13)
Cu2	0.02511 (17)	0.03088 (19)	0.02237 (16)	−0.00373 (14)	0.00162 (13)	−0.00551 (14)
Cu3	0.01595 (15)	0.0409 (2)	0.0351 (2)	−0.00491 (14)	0.00700 (13)	−0.01941 (16)
Cu4	0.01913 (15)	0.02818 (18)	0.02352 (16)	−0.00774 (13)	0.00518 (12)	−0.00593 (13)
Cl1	0.0216 (3)	0.0303 (4)	0.0323 (3)	−0.0077 (3)	−0.0032 (3)	0.0011 (3)
Cl2	0.0254 (3)	0.0527 (5)	0.0265 (3)	−0.0088 (3)	0.0084 (3)	−0.0048 (3)
Cl3	0.0178 (3)	0.0377 (4)	0.0364 (4)	−0.0069 (3)	0.0055 (3)	−0.0146 (3)
Cl4	0.0320 (3)	0.0325 (4)	0.0270 (3)	−0.0100 (3)	−0.0035 (3)	−0.0038 (3)
Cl5	0.0238 (3)	0.0510 (5)	0.0351 (4)	−0.0049 (3)	0.0145 (3)	−0.0015 (3)
Cl6	0.0554 (6)	0.0713 (7)	0.0395 (5)	0.0348 (5)	0.0163 (4)	0.0098 (4)
N11	0.0136 (9)	0.0250 (12)	0.0317 (12)	−0.0037 (8)	0.0049 (9)	−0.0061 (9)
N12	0.0161 (10)	0.0266 (13)	0.0485 (16)	−0.0053 (9)	0.0071 (10)	−0.0078 (11)
N13	0.0175 (13)	0.049 (2)	0.127 (4)	0.0027 (13)	−0.0002 (17)	0.006 (2)
N21	0.0349 (13)	0.0325 (14)	0.0240 (12)	−0.0034 (11)	−0.0015 (10)	−0.0082 (10)
N22	0.0273 (12)	0.0421 (15)	0.0240 (12)	−0.0001 (11)	0.0020 (10)	−0.0039 (11)
N23	0.0530 (19)	0.051 (2)	0.0406 (17)	0.0300 (16)	−0.0228 (15)	−0.0193 (15)
N31	0.0183 (11)	0.0410 (15)	0.0358 (14)	−0.0054 (10)	0.0040 (10)	−0.0198 (12)
N32	0.0215 (11)	0.0276 (12)	0.0237 (11)	0.0048 (9)	0.0007 (9)	−0.0023 (9)
N33	0.0396 (16)	0.055 (2)	0.057 (2)	0.0174 (15)	−0.0098 (14)	−0.0336 (16)
N41	0.0189 (10)	0.0317 (13)	0.0259 (12)	−0.0082 (9)	0.0033 (9)	−0.0044 (10)
N42	0.0404 (15)	0.0300 (14)	0.0340 (14)	−0.0092 (11)	−0.0094 (12)	−0.0012 (11)
N43	0.090 (3)	0.0332 (17)	0.050 (2)	0.0034 (17)	−0.0176 (19)	−0.0105 (15)
O1	0.0163 (8)	0.0279 (10)	0.0227 (9)	−0.0040 (7)	0.0036 (7)	−0.0080 (8)
O11	0.085 (3)	0.148 (4)	0.061 (2)	−0.048 (3)	0.031 (2)	−0.016 (2)
O12	0.0294 (16)	0.068 (2)	0.273 (7)	0.0062 (16)	−0.022 (3)	0.061 (3)
O13	0.0176 (12)	0.066 (2)	0.161 (4)	−0.0098 (13)	−0.0059 (17)	0.005 (2)
O21	0.0401 (18)	0.073 (3)	0.168 (4)	−0.0018 (17)	−0.004 (2)	−0.021 (3)
O22	0.097 (3)	0.0370 (16)	0.070 (2)	0.0127 (16)	−0.0530 (19)	−0.0170 (14)
O23	0.0467 (16)	0.104 (3)	0.0293 (13)	0.0229 (16)	−0.0096 (11)	−0.0139 (15)
O32	0.0461 (16)	0.088 (2)	0.077 (2)	0.0221 (16)	−0.0221 (15)	−0.0596 (19)
O33	0.0407 (15)	0.080 (2)	0.082 (2)	0.0242 (14)	−0.0056 (14)	−0.0527 (18)
O41	0.055 (2)	0.070 (2)	0.134 (4)	−0.0152 (17)	−0.038 (2)	0.037 (2)
O42	0.108 (3)	0.0457 (17)	0.0396 (15)	−0.0042 (17)	0.0097 (16)	−0.0170 (13)
O43	0.290 (7)	0.045 (2)	0.071 (3)	0.046 (3)	−0.061 (4)	−0.0152 (19)
C11	0.0193 (12)	0.0275 (14)	0.0320 (14)	−0.0053 (10)	0.0064 (10)	−0.0070 (11)
C12	0.0186 (13)	0.0289 (15)	0.053 (2)	0.0019 (11)	0.0050 (13)	−0.0024 (14)
C13	0.0141 (12)	0.0352 (17)	0.065 (2)	−0.0015 (11)	0.0042 (13)	−0.0069 (16)
C14	0.0221 (14)	0.0362 (18)	0.063 (2)	−0.0153 (13)	0.0074 (14)	−0.0067 (16)
C15	0.037 (2)	0.071 (3)	0.084 (3)	−0.022 (2)	0.026 (2)	−0.004 (2)
C16	0.0244 (14)	0.0344 (17)	0.052 (2)	−0.0068 (12)	0.0012 (13)	0.0044 (15)
C21	0.0313 (15)	0.0392 (17)	0.0229 (14)	−0.0076 (13)	0.0035 (11)	−0.0058 (12)
C22	0.0420 (18)	0.0303 (16)	0.0394 (18)	0.0068 (14)	−0.0137 (14)	−0.0113 (14)
C23	0.0357 (16)	0.0406 (18)	0.0284 (15)	0.0114 (14)	−0.0086 (12)	−0.0134 (13)
C24	0.0319 (16)	0.051 (2)	0.0359 (17)	−0.0074 (15)	−0.0003 (13)	0.0097 (15)
C25	0.042 (2)	0.043 (2)	0.069 (3)	0.0006 (17)	0.0065 (19)	0.0059 (19)
C26	0.069 (3)	0.048 (2)	0.0355 (19)	−0.025 (2)	−0.0065 (18)	−0.0030 (16)
C31	0.0176 (12)	0.0325 (15)	0.0245 (13)	−0.0023 (10)	0.0040 (10)	−0.0050 (11)
C32	0.0244 (13)	0.0346 (16)	0.0305 (15)	−0.0031 (12)	0.0001 (11)	−0.0095 (12)
C33	0.0273 (14)	0.0327 (16)	0.0310 (15)	0.0078 (12)	−0.0053 (11)	−0.0106 (12)
C34	0.017 (3)	0.035 (5)	0.030 (5)	0.010 (3)	0.003 (3)	0.000 (3)
C35	0.027 (3)	0.043 (5)	0.035 (4)	0.001 (3)	0.013 (3)	0.003 (3)
O31	0.033 (3)	0.037 (4)	0.052 (4)	0.004 (3)	0.013 (3)	0.011 (3)
C34A	0.022 (4)	0.045 (7)	0.040 (7)	0.019 (4)	−0.010 (4)	−0.005 (5)
C35A	0.023 (4)	0.091 (11)	0.045 (5)	−0.001 (7)	0.010 (4)	0.014 (8)
O31A	0.055 (6)	0.065 (7)	0.041 (4)	−0.023 (5)	−0.007 (3)	0.020 (4)
C36	0.0197 (13)	0.0441 (19)	0.0427 (18)	−0.0038 (12)	−0.0005 (12)	−0.0198 (15)
C41	0.0229 (13)	0.0331 (16)	0.0294 (14)	−0.0129 (11)	−0.0008 (11)	−0.0043 (12)
C42	0.0250 (13)	0.0332 (16)	0.0265 (14)	−0.0074 (11)	0.0038 (11)	−0.0078 (12)
C43	0.0394 (17)	0.0300 (16)	0.0348 (16)	−0.0058 (13)	−0.0052 (13)	−0.0074 (13)
C44	0.059 (2)	0.039 (2)	0.044 (2)	−0.0141 (17)	−0.0106 (18)	0.0024 (16)
C45	0.060 (3)	0.058 (3)	0.060 (3)	−0.004 (2)	−0.009 (2)	0.011 (2)
C46	0.049 (2)	0.0420 (19)	0.0265 (15)	−0.0144 (16)	0.0005 (14)	−0.0057 (14)

Geometric parameters (Å, º)

Cu1—O1	1.8960 (18)	N31—C31	1.337 (3)
Cu1—N11	1.949 (2)	N31—C32	1.368 (4)
Cu1—Cl1	2.4152 (9)	N32—C31	1.348 (4)
Cu1—Cl3	2.4351 (8)	N32—C33	1.381 (4)
Cu1—Cl2	2.4435 (9)	N32—C34	1.472 (9)
Cu2—O1	1.908 (2)	N32—C34A	1.516 (10)
Cu2—N21	1.955 (3)	N33—O33	1.226 (4)
Cu2—Cl6	2.3579 (10)	N33—O32	1.240 (4)
Cu2—Cl2	2.3726 (9)	N33—C33	1.423 (4)
Cu2—Cl4	2.4351 (9)	N41—C41	1.343 (4)
Cu3—O1	1.9022 (19)	N41—C42	1.368 (4)
Cu3—N31	1.955 (2)	N42—C41	1.342 (4)
Cu3—Cl5	2.3877 (10)	N42—C43	1.390 (4)
Cu3—Cl6	2.4113 (11)	N42—C44	1.484 (5)
Cu3—Cl3	2.4312 (8)	N43—O42	1.207 (4)
Cu4—O1	1.913 (2)	N43—O43	1.209 (5)
Cu4—N41	1.972 (3)	N43—C43	1.426 (5)
Cu4—Cl5	2.4186 (8)	O11—C15	1.404 (6)
Cu4—Cl4	2.4314 (9)	O21—C25	1.370 (5)
Cu4—Cl1	2.4332 (8)	O41—C45	1.458 (6)
N11—C11	1.335 (4)	C11—C16	1.480 (4)
N11—C12	1.356 (4)	C12—C13	1.359 (4)
N12—C11	1.350 (4)	C14—C15	1.501 (6)
N12—C13	1.373 (4)	C21—C26	1.482 (5)
N12—C14	1.481 (4)	C22—C23	1.352 (5)
N13—O12	1.195 (5)	C24—C25	1.510 (5)
N13—O13	1.217 (4)	C31—C36	1.480 (4)
N13—C13	1.426 (4)	C32—C33	1.348 (4)
N21—C21	1.334 (4)	C34—C35	1.490 (10)
N21—C22	1.359 (4)	C35—O31	1.411 (9)
N22—C21	1.356 (4)	C34A—C35A	1.495 (13)
N22—C23	1.376 (4)	C35A—O31A	1.413 (13)
N22—C24	1.469 (4)	C41—C46	1.480 (4)
N23—O23	1.236 (5)	C42—C43	1.343 (5)
N23—O22	1.246 (5)	C44—C45	1.474 (6)
N23—C23	1.425 (4)
O1—Cu1—N11	173.12 (10)	C31—N31—C32	107.4 (2)
O1—Cu1—Cl1	86.13 (6)	C31—N31—Cu3	125.4 (2)
N11—Cu1—Cl1	99.55 (7)	C32—N31—Cu3	127.1 (2)
O1—Cu1—Cl3	84.63 (6)	C31—N32—C33	106.1 (2)
N11—Cu1—Cl3	96.61 (7)	C31—N32—C34	123.8 (6)
Cl1—Cu1—Cl3	112.86 (3)	C33—N32—C34	129.5 (6)
O1—Cu1—Cl2	83.33 (6)	C31—N32—C34A	122.8 (7)
N11—Cu1—Cl2	91.01 (7)	C33—N32—C34A	129.4 (7)
Cl1—Cu1—Cl2	110.37 (3)	O33—N33—O32	124.6 (3)
Cl3—Cu1—Cl2	134.02 (3)	O33—N33—C33	119.6 (3)
O1—Cu2—N21	176.91 (10)	O32—N33—C33	115.9 (3)
O1—Cu2—Cl6	86.06 (6)	C41—N41—C42	107.0 (3)
N21—Cu2—Cl6	91.20 (8)	C41—N41—Cu4	129.2 (2)
O1—Cu2—Cl2	85.06 (6)	C42—N41—Cu4	123.4 (2)
N21—Cu2—Cl2	95.77 (8)	C41—N42—C43	106.5 (3)
Cl6—Cu2—Cl2	132.47 (4)	C41—N42—C44	125.2 (3)
O1—Cu2—Cl4	83.85 (6)	C43—N42—C44	128.2 (3)
N21—Cu2—Cl4	98.64 (8)	O42—N43—O43	124.0 (4)
Cl6—Cu2—Cl4	115.31 (4)	O42—N43—C43	118.0 (3)
Cl2—Cu2—Cl4	109.97 (3)	O43—N43—C43	117.9 (4)
O1—Cu3—N31	176.21 (10)	Cu1—O1—Cu3	110.80 (9)
O1—Cu3—Cl5	85.31 (6)	Cu1—O1—Cu2	108.46 (9)
N31—Cu3—Cl5	96.51 (9)	Cu3—O1—Cu2	108.36 (10)
O1—Cu3—Cl6	84.68 (6)	Cu1—O1—Cu4	108.74 (10)
N31—Cu3—Cl6	91.57 (9)	Cu3—O1—Cu4	109.55 (9)
Cl5—Cu3—Cl6	126.01 (4)	Cu2—O1—Cu4	110.93 (9)
O1—Cu3—Cl3	84.61 (6)	N11—C11—N12	110.5 (3)
N31—Cu3—Cl3	97.52 (7)	N11—C11—C16	125.5 (3)
Cl5—Cu3—Cl3	116.05 (3)	N12—C11—C16	124.0 (3)
Cl6—Cu3—Cl3	115.56 (4)	N11—C12—C13	107.8 (3)
O1—Cu4—N41	175.50 (9)	C12—C13—N12	108.4 (3)
O1—Cu4—Cl5	84.21 (6)	C12—C13—N13	126.4 (3)
N41—Cu4—Cl5	100.26 (7)	N12—C13—N13	125.2 (3)
O1—Cu4—Cl4	83.84 (6)	N12—C14—C15	112.4 (3)
N41—Cu4—Cl4	93.78 (7)	O11—C15—C14	109.9 (3)
Cl5—Cu4—Cl4	113.26 (3)	N21—C21—N22	110.5 (3)
O1—Cu4—Cl1	85.25 (6)	N21—C21—C26	125.7 (3)
N41—Cu4—Cl1	93.57 (7)	N22—C21—C26	123.7 (3)
Cl5—Cu4—Cl1	111.98 (3)	C23—C22—N21	108.1 (3)
Cl4—Cu4—Cl1	131.90 (3)	C22—C23—N22	108.5 (3)
Cu1—Cl1—Cu4	79.38 (2)	C22—C23—N23	125.7 (3)
Cu2—Cl2—Cu1	79.70 (2)	N22—C23—N23	125.6 (3)
Cu3—Cl3—Cu1	79.95 (3)	N22—C24—C25	111.6 (3)
Cu4—Cl4—Cu2	80.61 (2)	O21—C25—C24	111.5 (4)
Cu3—Cl5—Cu4	80.86 (3)	N31—C31—N32	110.3 (2)
Cu2—Cl6—Cu3	80.74 (3)	N31—C31—C36	125.6 (3)
C11—N11—C12	107.5 (2)	N32—C31—C36	124.2 (2)
C11—N11—Cu1	123.7 (2)	C33—C32—N31	107.8 (3)
C12—N11—Cu1	128.4 (2)	C32—C33—N32	108.4 (3)
C11—N12—C13	105.8 (2)	C32—C33—N33	126.4 (3)
C11—N12—C14	124.5 (3)	N32—C33—N33	125.1 (3)
C13—N12—C14	129.7 (3)	N32—C34—C35	110.2 (7)
O12—N13—O13	122.9 (3)	O31—C35—C34	110.9 (8)
O12—N13—C13	117.5 (3)	C35A—C34A—N32	112.3 (8)
O13—N13—C13	119.7 (4)	O31A—C35A—C34A	111.8 (9)
C21—N21—C22	107.3 (3)	N42—C41—N41	110.2 (3)
C21—N21—Cu2	126.3 (2)	N42—C41—C46	124.1 (3)
C22—N21—Cu2	126.1 (2)	N41—C41—C46	125.7 (3)
C21—N22—C23	105.6 (3)	C43—C42—N41	108.6 (3)
C21—N22—C24	125.2 (3)	C42—C43—N42	107.6 (3)
C23—N22—C24	127.8 (3)	C42—C43—N43	124.9 (3)
O23—N23—O22	125.4 (3)	N42—C43—N43	127.3 (3)
O23—N23—C23	118.8 (4)	C45—C44—N42	110.4 (3)
O22—N23—C23	115.9 (4)	O41—C45—C44	109.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O41—H41A···O31^i	0.89 (2)	2.13 (3)	2.738 (8)	125 (2)

Symmetry code: (i) x+1/2, y−1/2, z.