The crystal structure of the title compound, [Cu
2(C
8H
10N
4)
4(H
2O)
2](NO
3)
4·6H
2O, contains dinuclear complex cations with twofold rotation symmetry, in which two Cu
II centers are bridged by four 1,1′-dimethyl-2,2′-bi-1
H-imidazole ligands. Four N donors define the base of a slightly distorted square pyramid around each Cu
II center, the apical position being occupied by an aqua ligand. The nitrate ions and uncoordinated water molecules form a network of hydrogen bonds, in which the aqua ligands are also involved. The large Cu
Cu separation [3.092 (1) Å] is consistent with the absence of substantial metal–metal interactions, as suggested by the normal magnetic moment observed at room temperature.
Supporting information
CCDC reference: 601200
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- Disorder in solvent or counterion
- R factor = 0.061
- wR factor = 0.164
- Data-to-parameter ratio = 10.9
checkCIF/PLATON results
No syntax errors found
Alert level B
RINTA01_ALERT_3_B The value of Rint is greater than 0.15
Rint given 0.190
PLAT020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.19
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) ..... 20 Ang.
PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) ..... 20 Ang.
PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) ..... 10 Ang.
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N2'
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N1
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N3
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 42.00 Perc.
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
10 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 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
2 ALERT type 3 Indicator that the structure quality may be low
7 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRC-2 (Ahmed et al., 1973); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: UdMX (Maris, 2004).
Tetra-µ-1,1'-dimethyl-2,2'-bi-1
H-imidazole-bis[aquacopper(II)]
tetranitrate hexahydrate
top
Crystal data top
[Cu2(C8H10N4)4(H2O)2](NO3)4·6H2O | F(000) = 2424 |
Mr = 1168.05 | Dx = 1.578 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -C 2yc | Cell parameters from 25 reflections |
a = 21.3104 (2) Å | θ = 20.0–23.0° |
b = 22.0240 (2) Å | µ = 1.90 mm−1 |
c = 11.0725 (1) Å | T = 293 K |
β = 108.865 (1)° | Block, blue |
V = 4917.61 (8) Å3 | 0.35 × 0.26 × 0.25 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 3670 reflections with I > 2σ(I) |
Radiation source: Sealed Tube | Rint = 0.190 |
Graphite monochromator | θmax = 70.6°, θmin = 3.0° |
ω/2θ scans | h = −26→26 |
Absorption correction: gaussian (ABSORP in NRCVAX; Gabe et al., 1989) | k = −26→26 |
Tmin = 0.560, Tmax = 0.649 | l = −13→13 |
33942 measured reflections | 4 standard reflections every 60 min |
4727 independent reflections | intensity decay: 0.2% |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | w = 1/[σ2(Fo2) + (0.124P)2] where P = (Fo2 + 2Fc2)/3 |
4727 reflections | (Δ/σ)max = 0.003 |
434 parameters | Δρmax = 0.99 e Å−3 |
55 restraints | Δρmin = −0.98 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 | Uiso*/Ueq | Occ. (<1) |
Cu1 | 0.05150 (2) | 0.25410 (2) | 0.88548 (5) | 0.0311 (2) | |
N11 | 0.16038 (16) | 0.17882 (16) | 0.6731 (3) | 0.0474 (8) | |
C11 | 0.1688 (2) | 0.1472 (2) | 0.5626 (5) | 0.0587 (11) | |
H11A | 0.1984 | 0.1135 | 0.5914 | 0.088* | |
H11B | 0.1869 | 0.1748 | 0.5154 | 0.088* | |
H11C | 0.1265 | 0.1328 | 0.5086 | 0.088* | |
C12 | 0.10492 (19) | 0.18189 (16) | 0.7063 (4) | 0.0393 (8) | |
N13 | 0.11463 (16) | 0.21940 (14) | 0.8045 (3) | 0.0411 (7) | |
C14 | 0.1782 (2) | 0.24056 (18) | 0.8344 (4) | 0.0462 (9) | |
H14 | 0.1985 | 0.2678 | 0.8995 | 0.055* | |
C15 | 0.2065 (2) | 0.2153 (2) | 0.7535 (5) | 0.0542 (10) | |
H15 | 0.2495 | 0.2218 | 0.7531 | 0.065* | |
N21 | −0.04323 (18) | 0.08720 (14) | 0.8670 (4) | 0.0503 (8) | |
C21 | −0.0983 (3) | 0.0447 (2) | 0.8196 (6) | 0.0710 (15) | |
H21A | −0.1149 | 0.0339 | 0.8876 | 0.107* | |
H21B | −0.0831 | 0.0088 | 0.7883 | 0.107* | |
H21C | −0.1330 | 0.0633 | 0.7517 | 0.107* | |
C22 | −0.04479 (19) | 0.14815 (16) | 0.8536 (4) | 0.0393 (8) | |
N23 | 0.01609 (15) | 0.17032 (14) | 0.8985 (3) | 0.0401 (7) | |
C24 | 0.0574 (2) | 0.12166 (17) | 0.9417 (4) | 0.0469 (9) | |
H24 | 0.1033 | 0.1236 | 0.9781 | 0.056* | |
C25 | 0.0212 (2) | 0.07121 (19) | 0.9229 (5) | 0.0560 (11) | |
H25 | 0.0371 | 0.0320 | 0.9442 | 0.067* | |
N31 | 0.08823 (18) | 0.41991 (14) | 0.7358 (3) | 0.0486 (8) | |
C31 | 0.0880 (3) | 0.4620 (2) | 0.6340 (5) | 0.0639 (13) | |
H31A | 0.1317 | 0.4782 | 0.6499 | 0.096* | |
H31B | 0.0576 | 0.4946 | 0.6313 | 0.096* | |
H31C | 0.0744 | 0.4410 | 0.5538 | 0.096* | |
C32 | 0.07780 (18) | 0.35938 (16) | 0.7265 (4) | 0.0399 (8) | |
N33 | 0.07365 (15) | 0.33807 (13) | 0.8355 (3) | 0.0401 (7) | |
C34 | 0.0813 (2) | 0.38667 (17) | 0.9162 (4) | 0.0492 (10) | |
H34 | 0.0799 | 0.3851 | 0.9992 | 0.059* | |
C35 | 0.0911 (2) | 0.43706 (18) | 0.8558 (4) | 0.0550 (11) | |
H35 | 0.0984 | 0.4761 | 0.8894 | 0.066* | |
N41 | −0.11432 (17) | 0.32481 (15) | 0.9539 (3) | 0.0469 (8) | |
C41 | −0.1787 (2) | 0.3543 (2) | 0.9201 (5) | 0.0626 (12) | |
H41A | −0.1755 | 0.3900 | 0.9716 | 0.094* | |
H41B | −0.2105 | 0.3269 | 0.9348 | 0.094* | |
H41C | −0.1927 | 0.3656 | 0.8316 | 0.094* | |
C42 | −0.07100 (19) | 0.32475 (16) | 0.8880 (4) | 0.0401 (8) | |
N43 | −0.01993 (16) | 0.28853 (14) | 0.9455 (3) | 0.0404 (7) | |
C44 | −0.0321 (2) | 0.26486 (19) | 1.0508 (4) | 0.0461 (9) | |
H44 | −0.0048 | 0.2377 | 1.1086 | 0.055* | |
C45 | −0.0897 (2) | 0.2874 (2) | 1.0567 (4) | 0.0524 (10) | |
H45 | −0.1091 | 0.2791 | 1.1190 | 0.063* | |
O1 | 0.12606 (17) | 0.25507 (13) | 1.0768 (3) | 0.0499 (7) | |
H1A | 0.135 (3) | 0.2259 (14) | 1.125 (4) | 0.075* | |
H1B | 0.136 (3) | 0.2856 (13) | 1.121 (4) | 0.075* | |
O2 | 0.34449 (19) | 0.14740 (16) | 0.7583 (4) | 0.0634 (8) | |
H2A | 0.326 (3) | 0.124 (2) | 0.801 (5) | 0.095* | |
H2B | 0.3813 (14) | 0.133 (3) | 0.767 (6) | 0.095* | |
O3 | 0.1549 (2) | 0.1610 (2) | 0.2510 (4) | 0.0819 (12) | |
H3A | 0.174 (2) | 0.130 (2) | 0.241 (3) | 0.123* | |
H3B | 0.1147 (9) | 0.149 (4) | 0.236 (7) | 0.123* | |
O4 | 0.2693 (3) | 0.0615 (3) | 0.8221 (6) | 0.1027 (15) | |
H4A | 0.252 (4) | 0.029 (2) | 0.794 (8) | 0.154* | |
H4B | 0.254 (4) | 0.066 (4) | 0.881 (6) | 0.154* | |
N1 | 0.0072 (16) | 0.1015 (3) | 0.267 (3) | 0.050 (5) | 0.50 |
O11 | 0.0209 (6) | 0.1549 (3) | 0.258 (2) | 0.111 (5) | 0.50 |
O12 | −0.0441 (16) | 0.0827 (12) | 0.195 (3) | 0.179 (13) | 0.50 |
O13 | 0.0539 (12) | 0.0710 (8) | 0.322 (2) | 0.106 (5) | 0.50 |
N2 | 0.2347 (18) | 0.0547 (15) | 0.095 (3) | 0.110 (12) | 0.43 |
O21 | 0.219 (3) | 0.0545 (16) | 0.192 (3) | 0.101 (8) | 0.43 |
O22 | 0.2570 (16) | 0.0084 (14) | 0.064 (4) | 0.134 (10) | 0.43 |
O23 | 0.2178 (15) | 0.0951 (13) | 0.017 (2) | 0.124 (10) | 0.43 |
N2' | 0.2292 (11) | 0.0578 (7) | 0.1102 (18) | 0.084 (6) | 0.57 |
O21' | 0.2337 (16) | 0.0119 (9) | 0.050 (3) | 0.181 (13) | 0.57 |
O22' | 0.2352 (12) | 0.1085 (8) | 0.0674 (19) | 0.127 (7) | 0.57 |
O23' | 0.2211 (17) | 0.0528 (12) | 0.215 (2) | 0.107 (8) | 0.57 |
N3 | 0.4919 (8) | 0.0886 (3) | 0.7304 (15) | 0.047 (4) | 0.50 |
O31 | 0.4323 (4) | 0.0812 (3) | 0.6805 (9) | 0.068 (2) | 0.50 |
O32 | 0.5172 (11) | 0.0869 (8) | 0.8458 (13) | 0.149 (9) | 0.50 |
O33 | 0.5269 (6) | 0.0957 (7) | 0.6663 (14) | 0.104 (5) | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0338 (3) | 0.0278 (3) | 0.0338 (3) | 0.00040 (17) | 0.0138 (2) | −0.00021 (17) |
N11 | 0.0379 (17) | 0.0528 (19) | 0.056 (2) | 0.0040 (14) | 0.0207 (15) | −0.0056 (15) |
C11 | 0.053 (3) | 0.073 (3) | 0.058 (3) | 0.008 (2) | 0.030 (2) | −0.011 (2) |
C12 | 0.041 (2) | 0.0362 (18) | 0.044 (2) | 0.0050 (14) | 0.0184 (16) | −0.0001 (14) |
N13 | 0.0423 (17) | 0.0358 (15) | 0.0461 (17) | −0.0006 (13) | 0.0156 (14) | −0.0029 (13) |
C14 | 0.0340 (19) | 0.051 (2) | 0.053 (2) | −0.0021 (16) | 0.0125 (17) | −0.0031 (17) |
C15 | 0.037 (2) | 0.061 (3) | 0.066 (3) | −0.0005 (18) | 0.0191 (19) | −0.004 (2) |
N21 | 0.051 (2) | 0.0346 (16) | 0.066 (2) | −0.0016 (14) | 0.0201 (17) | 0.0095 (15) |
C21 | 0.061 (3) | 0.039 (2) | 0.109 (4) | −0.014 (2) | 0.023 (3) | 0.002 (2) |
C22 | 0.0411 (19) | 0.0353 (17) | 0.044 (2) | −0.0029 (14) | 0.0178 (16) | 0.0023 (15) |
N23 | 0.0402 (17) | 0.0376 (15) | 0.0429 (17) | 0.0024 (12) | 0.0141 (13) | 0.0024 (13) |
C24 | 0.047 (2) | 0.0381 (19) | 0.052 (2) | 0.0060 (16) | 0.0112 (18) | 0.0100 (17) |
C25 | 0.058 (3) | 0.038 (2) | 0.070 (3) | 0.0051 (18) | 0.017 (2) | 0.0146 (19) |
N31 | 0.062 (2) | 0.0346 (16) | 0.0509 (19) | −0.0081 (15) | 0.0204 (16) | −0.0006 (14) |
C31 | 0.090 (4) | 0.039 (2) | 0.066 (3) | −0.009 (2) | 0.030 (3) | 0.010 (2) |
C32 | 0.0401 (19) | 0.0353 (17) | 0.046 (2) | −0.0028 (14) | 0.0162 (16) | 0.0013 (15) |
N33 | 0.0461 (18) | 0.0363 (15) | 0.0397 (16) | −0.0014 (13) | 0.0165 (14) | −0.0016 (12) |
C34 | 0.066 (3) | 0.0378 (19) | 0.042 (2) | −0.0017 (18) | 0.0144 (19) | −0.0074 (16) |
C35 | 0.076 (3) | 0.0353 (19) | 0.054 (2) | −0.0069 (19) | 0.022 (2) | −0.0081 (17) |
N41 | 0.0503 (19) | 0.0489 (18) | 0.0485 (19) | 0.0072 (15) | 0.0256 (16) | −0.0006 (14) |
C41 | 0.050 (3) | 0.076 (3) | 0.071 (3) | 0.016 (2) | 0.032 (2) | 0.005 (3) |
C42 | 0.044 (2) | 0.0336 (17) | 0.046 (2) | 0.0022 (14) | 0.0194 (16) | −0.0030 (14) |
N43 | 0.0477 (18) | 0.0368 (15) | 0.0392 (16) | 0.0034 (13) | 0.0174 (13) | 0.0015 (12) |
C44 | 0.054 (2) | 0.050 (2) | 0.038 (2) | 0.0052 (18) | 0.0204 (18) | 0.0035 (16) |
C45 | 0.067 (3) | 0.053 (2) | 0.046 (2) | 0.004 (2) | 0.031 (2) | 0.0033 (18) |
O1 | 0.0526 (18) | 0.0493 (16) | 0.0407 (16) | −0.0005 (13) | 0.0053 (13) | −0.0019 (11) |
O2 | 0.068 (2) | 0.059 (2) | 0.067 (2) | 0.0034 (16) | 0.0266 (18) | −0.0037 (16) |
O3 | 0.086 (3) | 0.090 (3) | 0.064 (2) | −0.008 (2) | 0.017 (2) | 0.017 (2) |
O4 | 0.103 (4) | 0.105 (4) | 0.102 (4) | −0.026 (3) | 0.036 (3) | −0.002 (3) |
N1 | 0.064 (13) | 0.043 (3) | 0.040 (16) | 0.004 (5) | 0.011 (10) | 0.002 (4) |
O11 | 0.145 (15) | 0.045 (4) | 0.146 (9) | −0.003 (5) | 0.053 (15) | 0.007 (6) |
O12 | 0.113 (14) | 0.21 (2) | 0.18 (2) | −0.093 (14) | 0.005 (13) | −0.047 (17) |
O13 | 0.106 (12) | 0.072 (6) | 0.115 (11) | 0.037 (7) | 0.001 (9) | −0.013 (7) |
N2 | 0.075 (19) | 0.16 (3) | 0.102 (19) | −0.036 (19) | 0.039 (17) | −0.04 (2) |
O21 | 0.15 (2) | 0.081 (14) | 0.078 (12) | 0.006 (13) | 0.043 (13) | 0.009 (9) |
O22 | 0.107 (12) | 0.124 (18) | 0.19 (2) | 0.008 (10) | 0.068 (12) | −0.002 (16) |
O23 | 0.104 (16) | 0.17 (2) | 0.108 (16) | 0.043 (15) | 0.044 (13) | 0.050 (14) |
N2' | 0.065 (10) | 0.086 (11) | 0.101 (15) | −0.003 (7) | 0.028 (10) | 0.023 (10) |
O21' | 0.29 (4) | 0.140 (19) | 0.17 (2) | −0.039 (18) | 0.15 (2) | −0.030 (15) |
O22' | 0.129 (14) | 0.123 (11) | 0.134 (16) | −0.021 (8) | 0.047 (12) | 0.041 (12) |
O23' | 0.119 (14) | 0.112 (14) | 0.089 (11) | −0.037 (11) | 0.032 (9) | −0.008 (9) |
N3 | 0.061 (11) | 0.039 (3) | 0.035 (13) | 0.001 (4) | 0.006 (10) | 0.007 (4) |
O31 | 0.068 (5) | 0.055 (4) | 0.088 (6) | −0.006 (4) | 0.034 (5) | −0.009 (4) |
O32 | 0.20 (2) | 0.131 (14) | 0.068 (9) | −0.052 (16) | −0.023 (14) | −0.001 (9) |
O33 | 0.111 (9) | 0.113 (8) | 0.115 (12) | −0.011 (8) | 0.075 (10) | −0.015 (7) |
Geometric parameters (Å, º) top
Cu1—N13 | 1.994 (3) | N33—C34 | 1.370 (5) |
Cu1—N23 | 2.016 (3) | C34—C35 | 1.347 (6) |
Cu1—N33 | 2.029 (3) | C34—H34 | 0.9300 |
Cu1—N43 | 1.997 (3) | C35—H35 | 0.9300 |
Cu1—O1 | 2.199 (3) | N41—C42 | 1.349 (5) |
N11—C12 | 1.349 (5) | N41—C45 | 1.365 (5) |
N11—C15 | 1.356 (5) | N41—C41 | 1.454 (5) |
N11—C11 | 1.468 (5) | C41—H41A | 0.9600 |
C11—H11A | 0.9600 | C41—H41B | 0.9600 |
C11—H11B | 0.9600 | C41—H41C | 0.9600 |
C11—H11C | 0.9600 | C42—N43 | 1.333 (5) |
C12—N13 | 1.327 (5) | C42—C32i | 1.446 (5) |
C12—C22i | 1.444 (5) | N43—C44 | 1.377 (5) |
N13—C14 | 1.368 (5) | C44—C45 | 1.346 (6) |
C14—C15 | 1.351 (6) | C44—H44 | 0.9300 |
C14—H14 | 0.9300 | C45—H45 | 0.9300 |
C15—H15 | 0.9300 | O1—H1A | 0.82 (4) |
N21—C22 | 1.350 (5) | O1—H1B | 0.82 (3) |
N21—C25 | 1.357 (6) | O2—H2A | 0.87 (6) |
N21—C21 | 1.460 (5) | O2—H2B | 0.82 (4) |
C21—H21A | 0.9600 | O3—H3A | 0.82 (2) |
C21—H21B | 0.9600 | O3—H3B | 0.85 (3) |
C21—H21C | 0.9600 | O4—H4A | 0.82 (5) |
C22—N23 | 1.323 (5) | O4—H4B | 0.82 (7) |
C22—C12i | 1.444 (5) | N1—O12 | 1.197 (18) |
N23—C24 | 1.372 (5) | N1—O13 | 1.192 (17) |
C24—C25 | 1.331 (6) | N1—O11 | 1.223 (14) |
C24—H24 | 0.9300 | N2—O22 | 1.219 (19) |
C25—H25 | 0.9300 | N2—O23 | 1.213 (19) |
N31—C32 | 1.350 (5) | N2—O21 | 1.236 (17) |
N31—C35 | 1.363 (6) | N2'—O22' | 1.236 (6) |
N31—C31 | 1.458 (5) | N2'—O23' | 1.235 (6) |
C31—H31A | 0.9600 | N2'—O21' | 1.236 (6) |
C31—H31B | 0.9600 | N3—O33 | 1.195 (18) |
C31—H31C | 0.9600 | N3—O32 | 1.216 (17) |
C32—N33 | 1.324 (5) | N3—O31 | 1.221 (16) |
C32—C42i | 1.446 (5) | | |
| | | |
N13—Cu1—N43 | 173.04 (13) | N31—C31—H31B | 109.4 |
N23—Cu1—N33 | 168.22 (13) | H31A—C31—H31B | 109.5 |
N13—Cu1—N23 | 90.22 (13) | N31—C31—H31C | 109.5 |
N13—Cu1—N33 | 88.66 (13) | H31A—C31—H31C | 109.5 |
N43—Cu1—N23 | 88.88 (12) | H31B—C31—H31C | 109.5 |
N43—Cu1—N33 | 90.81 (12) | N33—C32—N31 | 109.8 (3) |
N13—Cu1—O1 | 93.13 (13) | N33—C32—C42i | 126.5 (3) |
N43—Cu1—O1 | 93.83 (13) | N31—C32—C42i | 123.7 (3) |
N23—Cu1—O1 | 96.34 (12) | C32—N33—C34 | 106.8 (3) |
N33—Cu1—O1 | 95.43 (12) | C32—N33—Cu1 | 131.4 (3) |
C12—N11—C15 | 107.7 (3) | C34—N33—Cu1 | 121.6 (3) |
C12—N11—C11 | 127.2 (4) | C35—C34—N33 | 108.9 (4) |
C15—N11—C11 | 124.8 (4) | C35—C34—H34 | 125.5 |
N11—C11—H11A | 109.4 | N33—C34—H34 | 125.5 |
N11—C11—H11B | 109.5 | C34—C35—N31 | 106.9 (3) |
H11A—C11—H11B | 109.5 | C34—C35—H35 | 126.5 |
N11—C11—H11C | 109.5 | N31—C35—H35 | 126.6 |
H11A—C11—H11C | 109.5 | C42—N41—C45 | 107.8 (3) |
H11B—C11—H11C | 109.5 | C42—N41—C41 | 128.0 (4) |
N13—C12—N11 | 109.7 (3) | C45—N41—C41 | 124.1 (4) |
N13—C12—C22i | 125.3 (3) | N41—C41—H41A | 109.4 |
N11—C12—C22i | 125.1 (3) | N41—C41—H41B | 109.5 |
C12—N13—C14 | 106.9 (3) | H41A—C41—H41B | 109.5 |
C12—N13—Cu1 | 131.1 (3) | N41—C41—H41C | 109.5 |
C14—N13—Cu1 | 121.3 (3) | H41A—C41—H41C | 109.5 |
C15—C14—N13 | 108.6 (4) | H41B—C41—H41C | 109.5 |
C15—C14—H14 | 125.7 | N43—C42—N41 | 109.8 (3) |
N13—C14—H14 | 125.7 | N43—C42—C32i | 124.7 (3) |
C14—C15—N11 | 107.2 (4) | N41—C42—C32i | 125.6 (3) |
C14—C15—H15 | 126.4 | C42—N43—C44 | 106.4 (3) |
N11—C15—H15 | 126.4 | C42—N43—Cu1 | 131.4 (3) |
C22—N21—C25 | 107.1 (3) | C44—N43—Cu1 | 120.7 (3) |
C22—N21—C21 | 127.6 (4) | C45—C44—N43 | 109.0 (4) |
C25—N21—C21 | 125.0 (4) | C45—C44—H44 | 125.5 |
N21—C21—H21A | 109.5 | N43—C44—H44 | 125.5 |
N21—C21—H21B | 109.5 | C44—C45—N41 | 107.0 (4) |
H21A—C21—H21B | 109.5 | C44—C45—H45 | 126.5 |
N21—C21—H21C | 109.5 | N41—C45—H45 | 126.5 |
H21A—C21—H21C | 109.5 | Cu1—O1—H1A | 125 (4) |
H21B—C21—H21C | 109.5 | Cu1—O1—H1B | 124 (4) |
N23—C22—N21 | 109.8 (3) | H1A—O1—H1B | 107 (5) |
N23—C22—C12i | 126.8 (3) | H2A—O2—H2B | 107 (5) |
N21—C22—C12i | 123.3 (3) | H3A—O3—H3B | 103 (6) |
C22—N23—C24 | 106.5 (3) | H4A—O4—H4B | 99 (5) |
C22—N23—Cu1 | 130.9 (3) | O12—N1—O13 | 125.1 (13) |
C24—N23—Cu1 | 121.8 (3) | O12—N1—O11 | 118 (2) |
C25—C24—N23 | 108.8 (4) | O13—N1—O11 | 114 (2) |
C25—C24—H24 | 125.6 | O22—N2—O23 | 118 (2) |
N23—C24—H24 | 125.6 | O22—N2—O21 | 119 (2) |
C24—C25—N21 | 107.8 (4) | O23—N2—O21 | 122 (3) |
C24—C25—H25 | 126.1 | O22'—N2'—O23' | 120.4 (9) |
N21—C25—H25 | 126.1 | O22'—N2'—O21' | 119.7 (10) |
C32—N31—C35 | 107.6 (3) | O23'—N2'—O21' | 119.9 (9) |
C32—N31—C31 | 127.6 (4) | O33—N3—O32 | 119 (2) |
C35—N31—C31 | 124.4 (4) | O33—N3—O31 | 120.4 (14) |
N31—C31—H31A | 109.5 | O32—N3—O31 | 121 (2) |
| | | |
C15—N11—C12—N13 | 0.4 (5) | C35—N31—C32—N33 | 0.4 (5) |
C11—N11—C12—N13 | −173.8 (4) | C31—N31—C32—N33 | −172.1 (4) |
C15—N11—C12—C22i | −178.1 (4) | C35—N31—C32—C42i | 179.1 (4) |
C11—N11—C12—C22i | 7.7 (7) | C31—N31—C32—C42i | 6.7 (7) |
N11—C12—N13—C14 | −0.2 (4) | N31—C32—N33—C34 | 0.4 (5) |
C22i—C12—N13—C14 | 178.3 (4) | C42i—C32—N33—C34 | −178.3 (4) |
N11—C12—N13—Cu1 | 170.0 (3) | N31—C32—N33—Cu1 | 174.5 (3) |
C22i—C12—N13—Cu1 | −11.5 (6) | C42i—C32—N33—Cu1 | −4.3 (6) |
N23—Cu1—N13—C12 | 50.8 (3) | N13—Cu1—N33—C32 | 46.9 (4) |
N33—Cu1—N13—C12 | −117.5 (3) | N43—Cu1—N33—C32 | −126.1 (4) |
O1—Cu1—N13—C12 | 147.1 (3) | N23—Cu1—N33—C32 | −37.7 (8) |
N23—Cu1—N13—C14 | −140.2 (3) | O1—Cu1—N33—C32 | 140.0 (3) |
N33—Cu1—N13—C14 | 51.5 (3) | N13—Cu1—N33—C34 | −139.7 (3) |
O1—Cu1—N13—C14 | −43.9 (3) | N43—Cu1—N33—C34 | 47.2 (3) |
C12—N13—C14—C15 | −0.1 (5) | N23—Cu1—N33—C34 | 135.6 (6) |
Cu1—N13—C14—C15 | −171.5 (3) | O1—Cu1—N33—C34 | −46.7 (3) |
N13—C14—C15—N11 | 0.4 (5) | C32—N33—C34—C35 | −1.0 (5) |
C12—N11—C15—C14 | −0.5 (5) | Cu1—N33—C34—C35 | −175.8 (3) |
C11—N11—C15—C14 | 173.9 (4) | N33—C34—C35—N31 | 1.2 (5) |
C25—N21—C22—N23 | 0.3 (5) | C32—N31—C35—C34 | −1.0 (5) |
C21—N21—C22—N23 | −173.8 (4) | C31—N31—C35—C34 | 171.8 (4) |
C25—N21—C22—C12i | 177.9 (4) | C45—N41—C42—N43 | 0.1 (5) |
C21—N21—C22—C12i | 3.8 (7) | C41—N41—C42—N43 | −175.1 (4) |
N21—C22—N23—C24 | 0.0 (4) | C45—N41—C42—C32i | −178.9 (4) |
C12i—C22—N23—C24 | −177.5 (4) | C41—N41—C42—C32i | 6.0 (7) |
N21—C22—N23—Cu1 | 169.6 (3) | N41—C42—N43—C44 | 0.3 (4) |
C12i—C22—N23—Cu1 | −7.9 (6) | C32i—C42—N43—C44 | 179.3 (4) |
N13—Cu1—N23—C22 | −122.8 (3) | N41—C42—N43—Cu1 | 166.0 (3) |
N43—Cu1—N23—C22 | 50.3 (3) | C32i—C42—N43—Cu1 | −15.0 (6) |
N33—Cu1—N23—C22 | −38.3 (8) | N23—Cu1—N43—C42 | −115.9 (3) |
O1—Cu1—N23—C22 | 144.0 (3) | N33—Cu1—N43—C42 | 52.3 (3) |
N13—Cu1—N23—C24 | 45.5 (3) | O1—Cu1—N43—C42 | 147.8 (3) |
N43—Cu1—N23—C24 | −141.4 (3) | N23—Cu1—N43—C44 | 48.1 (3) |
N33—Cu1—N23—C24 | 130.0 (6) | N33—Cu1—N43—C44 | −143.7 (3) |
O1—Cu1—N23—C24 | −47.7 (3) | O1—Cu1—N43—C44 | −48.2 (3) |
C22—N23—C24—C25 | −0.3 (5) | C42—N43—C44—C45 | −0.7 (5) |
Cu1—N23—C24—C25 | −171.1 (3) | Cu1—N43—C44—C45 | −168.2 (3) |
N23—C24—C25—N21 | 0.4 (5) | N43—C44—C45—N41 | 0.7 (5) |
C22—N21—C25—C24 | −0.4 (5) | C42—N41—C45—C44 | −0.5 (5) |
C21—N21—C25—C24 | 173.9 (5) | C41—N41—C45—C44 | 174.9 (4) |
Symmetry code: (i) −x, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O3ii | 0.82 (4) | 1.94 (4) | 2.760 (5) | 175 (5) |
O1—H1B···O2iii | 0.82 (3) | 1.94 (3) | 2.757 (5) | 173 (5) |
O2—H2A···O4 | 0.87 (6) | 1.90 (6) | 2.717 (6) | 155 (7) |
O2—H2B···O31 | 0.82 (4) | 2.02 (4) | 2.722 (9) | 143 (6) |
O2—H2B···O33iv | 0.82 (4) | 2.03 (5) | 2.833 (15) | 166 (6) |
O3—H3A···O23′ | 0.82 (4) | 2.04 (5) | 2.86 (3) | 180 (5) |
O3—H3A···O21 | 0.82 (4) | 2.08 (6) | 2.89 (5) | 173 (3) |
O3—H3B···O11 | 0.85 (3) | 2.09 (2) | 2.883 (12) | 153 (7) |
O4—H4A···O23′v | 0.82 (5) | 2.02 (3) | 2.83 (3) | 171 (9) |
O4—H4A···O21v | 0.82 (5) | 2.15 (7) | 2.96 (4) | 167 (9) |
O4—H4B···O23ii | 0.82 (7) | 2.01 (3) | 2.81 (3) | 168 (9) |
Symmetry codes: (ii) x, y, z+1; (iii) −x+1/2, −y+1/2, −z+2; (iv) −x+1, y, −z+3/2; (v) x, −y, z+1/2. |