Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048318/cv2135sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048318/cv2135Isup2.hkl |
CCDC reference: 629637
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- Disorder in solvent or counterion
- R factor = 0.042
- wR factor = 0.119
- Data-to-parameter ratio = 11.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT221_ALERT_4_B Large Solvent/Anion O Ueq(max)/Ueq(min) ... 4.41 Ratio
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Cu1 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for O3 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for O4' PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for O5 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for O6' PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for O3' PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for O5' PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for O6 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 44.00 Perc. PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........ O6 PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........ O6' PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT432_ALERT_2_C Short Inter X...Y Contact O6' .. C5 .. 2.96 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 36.40 Deg. O3 -CL1 -O3' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 25.30 Deg. O5 -CL1 -O5' 1.555 1.555 1.555 PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.03
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.02 From the CIF: _reflns_number_total 2815 Count of symmetry unique reflns 1737 Completeness (_total/calc) 162.06% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1078 Fraction of Friedel pairs measured 0.621 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 18 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 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 1 ALERT type 3 Indicator that the structure quality may be low 12 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
[Cu(C9H14N6)2(H2O)3]2+·2ClO4− | Dx = 1.522 Mg m−3 |
Mr = 729.01 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P41212 | Cell parameters from 4719 reflections |
Hall symbol: P_4abw_2nw | θ = 2.3–22.6° |
a = 9.2157 (3) Å | µ = 0.93 mm−1 |
c = 37.458 (3) Å | T = 293 K |
V = 3181.2 (3) Å3 | Block, blue |
Z = 4 | 0.20 × 0.14 × 0.12 mm |
F(000) = 1508 |
Bruker APEXII CCD area-detector diffractometer | 2815 independent reflections |
Radiation source: fine-focus sealed tube | 2581 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
φ and ω scans | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | h = −10→9 |
Tmin = 0.855, Tmax = 0.899 | k = −10→10 |
17426 measured reflections | l = −38→44 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.119 | w = 1/[σ2(Fo2) + (0.0631P)2 + 2.3565P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
2815 reflections | Δρmax = 0.53 e Å−3 |
252 parameters | Δρmin = −0.35 e Å−3 |
24 restraints | Absolute structure: Flack (1983), 1078 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.00 (3) |
Experimental. CHN analysis, found: C 29.57, H 4.67, N 23.14%, calculated (C18H34Cl2CuN12O11): C 29.63, H 4.66, N 23.04%. |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cu1 | 1.01471 (5) | 0.01471 (5) | 0.0000 | 0.0418 (2) | |
O1 | 1.0943 (4) | −0.0631 (4) | 0.04426 (7) | 0.0678 (10) | |
O2 | 0.8435 (4) | −0.1565 (4) | 0.0000 | 0.102 (2) | |
N1 | 0.9259 (3) | 0.1827 (3) | 0.02630 (7) | 0.0417 (7) | |
N2 | 0.7856 (4) | 0.3481 (4) | 0.04636 (8) | 0.0444 (7) | |
N3 | 0.9200 (4) | 0.3872 (4) | 0.05805 (9) | 0.0544 (9) | |
N4 | 0.5943 (4) | 0.3969 (4) | 0.08796 (8) | 0.0472 (7) | |
N5 | 0.5058 (4) | 0.2790 (4) | 0.08809 (8) | 0.0528 (8) | |
N6 | 0.5248 (4) | 0.3735 (4) | 0.14299 (8) | 0.0559 (9) | |
C1 | 1.1626 (6) | 0.2832 (7) | 0.05099 (16) | 0.0870 (18) | |
H1A | 1.2103 | 0.3106 | 0.0292 | 0.131* | |
H1B | 1.1931 | 0.1875 | 0.0578 | 0.131* | |
H1C | 1.1876 | 0.3508 | 0.0695 | 0.131* | |
C2 | 1.0026 (5) | 0.2843 (5) | 0.04546 (10) | 0.0510 (9) | |
C3 | 0.7891 (4) | 0.2276 (4) | 0.02692 (8) | 0.0393 (8) | |
C4 | 0.6615 (4) | 0.1607 (5) | 0.01008 (11) | 0.0555 (11) | |
H4A | 0.6032 | 0.1145 | 0.0280 | 0.083* | |
H4B | 0.6927 | 0.0898 | −0.0071 | 0.083* | |
H4C | 0.6053 | 0.2342 | −0.0017 | 0.083* | |
C5 | 0.6638 (5) | 0.4429 (4) | 0.05528 (10) | 0.0494 (9) | |
H5A | 0.6983 | 0.5417 | 0.0580 | 0.059* | |
H5B | 0.5937 | 0.4414 | 0.0360 | 0.059* | |
C6 | 0.3718 (6) | 0.1504 (7) | 0.13545 (14) | 0.0790 (15) | |
H6A | 0.3624 | 0.0760 | 0.1177 | 0.118* | |
H6B | 0.2778 | 0.1896 | 0.1409 | 0.118* | |
H6C | 0.4136 | 0.1099 | 0.1567 | 0.118* | |
C7 | 0.4676 (5) | 0.2683 (5) | 0.12163 (11) | 0.0544 (10) | |
C8 | 0.6064 (4) | 0.4534 (5) | 0.12109 (10) | 0.0501 (10) | |
C9 | 0.6976 (6) | 0.5776 (6) | 0.13108 (12) | 0.0727 (14) | |
H9A | 0.6394 | 0.6639 | 0.1319 | 0.109* | |
H9B | 0.7734 | 0.5896 | 0.1137 | 0.109* | |
H9C | 0.7397 | 0.5606 | 0.1541 | 0.109* | |
Cl1 | 0.48718 (12) | 0.80598 (13) | 0.05379 (4) | 0.0697 (3) | |
O3 | 0.6024 (8) | 0.8427 (10) | 0.0781 (2) | 0.208 (10) | 0.50 |
O4 | 0.5443 (10) | 0.7964 (9) | 0.01805 (11) | 0.158 (6) | 0.50 |
O5 | 0.3768 (6) | 0.9162 (6) | 0.0550 (3) | 0.115 (5) | 0.50 |
O6 | 0.4256 (7) | 0.6683 (4) | 0.0637 (2) | 0.121 (5) | 0.50 |
O3' | 0.6375 (3) | 0.8473 (8) | 0.0557 (2) | 0.087 (3) | 0.50 |
O4' | 0.4358 (7) | 0.7706 (11) | 0.08906 (12) | 0.200 (8) | 0.50 |
O5' | 0.4033 (6) | 0.9244 (6) | 0.03967 (19) | 0.063 (2) | 0.50 |
O6' | 0.4720 (10) | 0.6814 (6) | 0.0310 (2) | 0.278 (15) | 0.50 |
H1A' | 1.046 (4) | −0.096 (5) | 0.0619 (8) | 0.079 (17)* | |
H1B' | 1.186 (5) | −0.070 (6) | 0.0452 (12) | 0.088 (19)* | |
H2A | 0.794 (7) | −0.149 (10) | 0.0191 (11) | 0.15 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0481 (3) | 0.0481 (3) | 0.0291 (3) | 0.0142 (3) | 0.00304 (15) | −0.00304 (15) |
O1 | 0.063 (2) | 0.105 (3) | 0.0350 (14) | 0.0375 (19) | 0.0123 (13) | 0.0182 (15) |
O2 | 0.072 (2) | 0.072 (2) | 0.162 (7) | −0.015 (3) | 0.033 (3) | −0.033 (3) |
N1 | 0.0466 (17) | 0.0500 (18) | 0.0285 (13) | 0.0092 (14) | −0.0004 (13) | −0.0063 (13) |
N2 | 0.0516 (19) | 0.0464 (18) | 0.0352 (15) | 0.0112 (14) | 0.0029 (14) | −0.0060 (14) |
N3 | 0.052 (2) | 0.061 (2) | 0.0494 (19) | 0.0041 (17) | −0.0034 (16) | −0.0185 (17) |
N4 | 0.0491 (19) | 0.0503 (19) | 0.0423 (16) | 0.0072 (14) | 0.0095 (14) | −0.0048 (14) |
N5 | 0.052 (2) | 0.063 (2) | 0.0431 (17) | 0.0041 (18) | 0.0032 (15) | −0.0121 (15) |
N6 | 0.055 (2) | 0.074 (2) | 0.0386 (16) | −0.0008 (18) | 0.0053 (16) | −0.0067 (16) |
C1 | 0.057 (3) | 0.103 (4) | 0.102 (4) | 0.010 (3) | −0.020 (3) | −0.037 (4) |
C2 | 0.050 (2) | 0.059 (2) | 0.044 (2) | 0.010 (2) | −0.0023 (18) | −0.0118 (17) |
C3 | 0.041 (2) | 0.048 (2) | 0.0283 (15) | 0.0085 (15) | 0.0038 (14) | −0.0007 (15) |
C4 | 0.046 (2) | 0.061 (2) | 0.059 (3) | 0.0053 (19) | 0.0017 (18) | −0.013 (2) |
C5 | 0.060 (2) | 0.048 (2) | 0.0407 (18) | 0.0185 (18) | 0.0119 (18) | −0.0003 (17) |
C6 | 0.078 (3) | 0.094 (4) | 0.064 (3) | −0.015 (3) | 0.018 (3) | 0.001 (3) |
C7 | 0.047 (2) | 0.066 (3) | 0.050 (2) | 0.004 (2) | 0.0097 (19) | −0.0035 (19) |
C8 | 0.048 (2) | 0.063 (3) | 0.0391 (19) | 0.0097 (19) | 0.0039 (16) | −0.0099 (17) |
C9 | 0.096 (4) | 0.076 (3) | 0.046 (2) | −0.017 (3) | 0.003 (2) | −0.009 (2) |
Cl1 | 0.0510 (6) | 0.0713 (7) | 0.0868 (8) | 0.0075 (6) | −0.0081 (6) | 0.0023 (6) |
O3 | 0.28 (2) | 0.120 (11) | 0.223 (18) | −0.017 (12) | −0.174 (17) | 0.033 (12) |
O4 | 0.181 (12) | 0.184 (13) | 0.109 (7) | −0.050 (10) | 0.072 (8) | −0.055 (8) |
O5 | 0.089 (7) | 0.087 (7) | 0.169 (12) | 0.023 (6) | 0.025 (7) | 0.011 (7) |
O6 | 0.060 (5) | 0.056 (5) | 0.246 (15) | 0.005 (4) | 0.033 (7) | −0.024 (6) |
O3' | 0.025 (3) | 0.142 (8) | 0.094 (6) | 0.000 (4) | −0.019 (3) | 0.023 (6) |
O4' | 0.113 (9) | 0.261 (18) | 0.226 (16) | 0.005 (11) | 0.015 (10) | 0.170 (15) |
O5' | 0.037 (3) | 0.073 (5) | 0.078 (5) | 0.013 (3) | 0.005 (4) | 0.010 (4) |
O6' | 0.26 (2) | 0.195 (17) | 0.38 (3) | 0.159 (16) | −0.22 (2) | −0.214 (19) |
Cu1—O1i | 1.949 (3) | C4—H4C | 0.9600 |
Cu1—O1 | 1.949 (3) | C5—H5A | 0.9700 |
Cu1—N1i | 2.009 (3) | C5—H5B | 0.9700 |
Cu1—N1 | 2.009 (3) | C6—C7 | 1.492 (7) |
Cu1—O2 | 2.232 (6) | C6—H6A | 0.9600 |
O1—H1A' | 0.85 (3) | C6—H6B | 0.9600 |
O1—H1B' | 0.85 (4) | C6—H6C | 0.9600 |
O2—H2A | 0.85 (5) | C8—C9 | 1.469 (6) |
N1—C3 | 1.328 (4) | C9—H9A | 0.9600 |
N1—C2 | 1.375 (5) | C9—H9B | 0.9600 |
N2—C3 | 1.328 (5) | C9—H9C | 0.9600 |
N2—N3 | 1.362 (5) | Cl1—O5 | 1.4382 (9) |
N2—C5 | 1.461 (5) | Cl1—O3 | 1.4382 (9) |
N3—C2 | 1.304 (5) | Cl1—O6' | 1.4383 (9) |
N4—C8 | 1.350 (5) | Cl1—O3' | 1.4384 (9) |
N4—N5 | 1.358 (5) | Cl1—O5' | 1.4385 (9) |
N4—C5 | 1.445 (5) | Cl1—O6 | 1.4385 (9) |
N5—C7 | 1.308 (5) | Cl1—O4' | 1.4407 (9) |
N6—C8 | 1.334 (5) | Cl1—O4 | 1.4414 (9) |
N6—C7 | 1.363 (6) | O3—O3' | 0.899 (10) |
C1—C2 | 1.489 (7) | O3—O4' | 1.723 (8) |
C1—H1A | 0.9600 | O4—O6' | 1.343 (9) |
C1—H1B | 0.9600 | O4—O3' | 1.717 (9) |
C1—H1C | 0.9600 | O5—O5' | 0.630 (10) |
C3—C4 | 1.470 (6) | O6—O6' | 1.305 (9) |
C4—H4A | 0.9600 | O6—O4' | 1.341 (9) |
C4—H4B | 0.9600 | ||
O1i—Cu1—O1 | 179.3 (3) | N6—C7—C6 | 122.9 (4) |
O1i—Cu1—N1i | 91.12 (12) | N6—C8—N4 | 107.8 (4) |
O1—Cu1—N1i | 88.70 (12) | N6—C8—C9 | 126.6 (4) |
O1i—Cu1—N1 | 88.70 (12) | N4—C8—C9 | 125.6 (4) |
O1—Cu1—N1 | 91.12 (12) | C8—C9—H9A | 109.5 |
N1i—Cu1—N1 | 150.25 (19) | C8—C9—H9B | 109.5 |
O1i—Cu1—O2 | 90.35 (12) | H9A—C9—H9B | 109.5 |
O1—Cu1—O2 | 90.35 (12) | C8—C9—H9C | 109.5 |
N1i—Cu1—O2 | 104.88 (9) | H9A—C9—H9C | 109.5 |
N1—Cu1—O2 | 104.88 (9) | H9B—C9—H9C | 109.5 |
Cu1—O1—H1A' | 126 (3) | O5—Cl1—O3 | 109.60 (9) |
Cu1—O1—H1B' | 116 (3) | O5—Cl1—O6' | 120.9 (6) |
H1A'—O1—H1B' | 117 (4) | O3—Cl1—O6' | 129.5 (6) |
Cu1—O2—H2A | 109 (5) | O5—Cl1—O3' | 119.5 (5) |
C3—N1—C2 | 105.5 (3) | O3—Cl1—O3' | 36.4 (4) |
C3—N1—Cu1 | 129.5 (3) | O6'—Cl1—O3' | 109.57 (9) |
C2—N1—Cu1 | 124.8 (3) | O5—Cl1—O5' | 25.3 (4) |
C3—N2—N3 | 112.0 (3) | O3—Cl1—O5' | 116.8 (6) |
C3—N2—C5 | 130.1 (4) | O6'—Cl1—O5' | 109.56 (9) |
N3—N2—C5 | 117.9 (3) | O3'—Cl1—O5' | 109.58 (9) |
C2—N3—N2 | 102.8 (3) | O5—Cl1—O6 | 109.59 (9) |
C8—N4—N5 | 110.8 (3) | O3—Cl1—O6 | 109.58 (9) |
C8—N4—C5 | 129.0 (4) | O6'—Cl1—O6 | 54.0 (4) |
N5—N4—C5 | 120.2 (3) | O3'—Cl1—O6 | 126.9 (5) |
C7—N5—N4 | 103.0 (3) | O5'—Cl1—O6 | 123.5 (5) |
C8—N6—C7 | 104.4 (3) | O5—Cl1—O4' | 84.1 (4) |
C2—C1—H1A | 109.5 | O3—Cl1—O4' | 73.5 (4) |
C2—C1—H1B | 109.5 | O6'—Cl1—O4' | 109.42 (9) |
H1A—C1—H1B | 109.5 | O3'—Cl1—O4' | 109.30 (9) |
C2—C1—H1C | 109.5 | O5'—Cl1—O4' | 109.40 (9) |
H1A—C1—H1C | 109.5 | O6—Cl1—O4' | 55.5 (4) |
H1B—C1—H1C | 109.5 | O5—Cl1—O4 | 109.38 (9) |
N3—C2—N1 | 112.6 (4) | O3—Cl1—O4 | 109.37 (9) |
N3—C2—C1 | 122.2 (4) | O6'—Cl1—O4 | 55.6 (4) |
N1—C2—C1 | 125.2 (4) | O3'—Cl1—O4 | 73.2 (4) |
N1—C3—N2 | 107.1 (3) | O5'—Cl1—O4 | 84.3 (4) |
N1—C3—C4 | 128.4 (3) | O6—Cl1—O4 | 109.31 (9) |
N2—C3—C4 | 124.5 (3) | O4'—Cl1—O4 | 163.3 (4) |
C3—C4—H4A | 109.5 | O3'—O3—Cl1 | 71.8 (2) |
C3—C4—H4B | 109.5 | O3'—O3—O4' | 124.2 (3) |
H4A—C4—H4B | 109.5 | Cl1—O3—O4' | 53.3 (2) |
C3—C4—H4C | 109.5 | O6'—O4—Cl1 | 62.1 (2) |
H4A—C4—H4C | 109.5 | O6'—O4—O3' | 99.7 (4) |
H4B—C4—H4C | 109.5 | Cl1—O4—O3' | 53.3 (2) |
N4—C5—N2 | 111.0 (3) | O5'—O5—Cl1 | 77.4 (2) |
N4—C5—H5A | 109.4 | O6'—O6—O4' | 125.30 (11) |
N2—C5—H5A | 109.4 | O6'—O6—Cl1 | 63.0 (2) |
N4—C5—H5B | 109.4 | O4'—O6—Cl1 | 62.3 (2) |
N2—C5—H5B | 109.4 | O3—O3'—Cl1 | 71.8 (2) |
H5A—C5—H5B | 108.0 | O3—O3'—O4 | 124.95 (17) |
C7—C6—H6A | 109.5 | Cl1—O3'—O4 | 53.5 (2) |
C7—C6—H6B | 109.5 | O6—O4'—Cl1 | 62.2 (2) |
H6A—C6—H6B | 109.5 | O6—O4'—O3 | 99.5 (4) |
C7—C6—H6C | 109.5 | Cl1—O4'—O3 | 53.2 (2) |
H6A—C6—H6C | 109.5 | O5—O5'—Cl1 | 77.3 (2) |
H6B—C6—H6C | 109.5 | O6—O6'—O4 | 125.05 (16) |
N5—C7—N6 | 114.0 (4) | O6—O6'—Cl1 | 63.0 (2) |
N5—C7—C6 | 123.2 (4) | O4—O6'—Cl1 | 62.3 (2) |
O1i—Cu1—N1—C3 | 55.5 (3) | O3—Cl1—O6—O6' | −125.1 (7) |
O1—Cu1—N1—C3 | −125.2 (3) | O3'—Cl1—O6—O6' | −88.4 (5) |
N1i—Cu1—N1—C3 | 145.4 (3) | O5'—Cl1—O6—O6' | 90.8 (4) |
O2—Cu1—N1—C3 | −34.6 (3) | O4'—Cl1—O6—O6' | −177.6 (7) |
O1i—Cu1—N1—C2 | −118.3 (3) | O4—Cl1—O6—O6' | −5.3 (7) |
O1—Cu1—N1—C2 | 61.0 (3) | O5—Cl1—O6—O4' | −67.9 (5) |
N1i—Cu1—N1—C2 | −28.3 (3) | O3—Cl1—O6—O4' | 52.4 (5) |
O2—Cu1—N1—C2 | 151.7 (3) | O6'—Cl1—O6—O4' | 177.6 (7) |
C3—N2—N3—C2 | −1.2 (4) | O3'—Cl1—O6—O4' | 89.2 (4) |
C5—N2—N3—C2 | −178.9 (3) | O5'—Cl1—O6—O4' | −91.6 (5) |
C8—N4—N5—C7 | −0.2 (4) | O4—Cl1—O6—O4' | 172.3 (5) |
C5—N4—N5—C7 | 178.1 (3) | O4'—O3—O3'—Cl1 | 10.5 (9) |
N2—N3—C2—N1 | 0.2 (4) | Cl1—O3—O3'—O4 | −6.2 (8) |
N2—N3—C2—C1 | 178.6 (5) | O4'—O3—O3'—O4 | 4.2 (17) |
C3—N1—C2—N3 | 0.8 (4) | O5—Cl1—O3'—O3 | 83.2 (7) |
Cu1—N1—C2—N3 | 175.9 (3) | O6'—Cl1—O3'—O3 | −130.9 (10) |
C3—N1—C2—C1 | −177.5 (5) | O5'—Cl1—O3'—O3 | 108.9 (10) |
Cu1—N1—C2—C1 | −2.5 (6) | O6—Cl1—O3'—O3 | −71.8 (9) |
C2—N1—C3—N2 | −1.5 (4) | O4'—Cl1—O3'—O3 | −11.0 (10) |
Cu1—N1—C3—N2 | −176.2 (2) | O4—Cl1—O3'—O3 | −173.6 (9) |
C2—N1—C3—C4 | 178.9 (4) | O5—Cl1—O3'—O4 | −103.1 (3) |
Cu1—N1—C3—C4 | 4.2 (6) | O3—Cl1—O3'—O4 | 173.6 (9) |
N3—N2—C3—N1 | 1.8 (4) | O6'—Cl1—O3'—O4 | 42.8 (5) |
C5—N2—C3—N1 | 179.1 (3) | O5'—Cl1—O3'—O4 | −77.5 (4) |
N3—N2—C3—C4 | −178.7 (4) | O6—Cl1—O3'—O4 | 101.8 (3) |
C5—N2—C3—C4 | −1.3 (6) | O4'—Cl1—O3'—O4 | 162.7 (4) |
C8—N4—C5—N2 | 102.1 (4) | O6'—O4—O3'—O3 | −36.7 (10) |
N5—N4—C5—N2 | −75.9 (5) | Cl1—O4—O3'—O3 | 7.4 (10) |
C3—N2—C5—N4 | 89.9 (5) | O6'—O4—O3'—Cl1 | −44.0 (3) |
N3—N2—C5—N4 | −92.8 (4) | O6'—O6—O4'—Cl1 | 2.7 (8) |
N4—N5—C7—N6 | 0.9 (5) | O6'—O6—O4'—O3 | −36.5 (8) |
N4—N5—C7—C6 | −178.3 (4) | Cl1—O6—O4'—O3 | −39.19 (17) |
C8—N6—C7—N5 | −1.2 (5) | O5—Cl1—O4'—O6 | 118.7 (3) |
C8—N6—C7—C6 | 178.0 (4) | O3—Cl1—O4'—O6 | −128.9 (4) |
C7—N6—C8—N4 | 1.0 (4) | O6'—Cl1—O4'—O6 | −2.1 (6) |
C7—N6—C8—C9 | −177.0 (5) | O3'—Cl1—O4'—O6 | −122.1 (6) |
N5—N4—C8—N6 | −0.5 (4) | O5'—Cl1—O4'—O6 | 117.9 (6) |
C5—N4—C8—N6 | −178.7 (3) | O4—Cl1—O4'—O6 | −26.3 (16) |
N5—N4—C8—C9 | 177.5 (4) | O5—Cl1—O4'—O3 | −112.47 (17) |
C5—N4—C8—C9 | −0.6 (7) | O6'—Cl1—O4'—O3 | 126.8 (6) |
O5—Cl1—O3—O3' | −113.5 (9) | O3'—Cl1—O4'—O3 | 6.8 (6) |
O6'—Cl1—O3—O3' | 67.3 (10) | O5'—Cl1—O4'—O3 | −113.2 (6) |
O5'—Cl1—O3—O3' | −87.0 (9) | O6—Cl1—O4'—O3 | 128.9 (4) |
O6—Cl1—O3—O3' | 126.3 (9) | O4—Cl1—O4'—O3 | 102.6 (14) |
O4'—Cl1—O3—O3' | 169.2 (10) | O3'—O3—O4'—O6 | 31.8 (12) |
O4—Cl1—O3—O3' | 6.4 (9) | Cl1—O3—O4'—O6 | 44.3 (3) |
O5—Cl1—O3—O4' | 77.4 (4) | O3'—O3—O4'—Cl1 | −12.4 (11) |
O6'—Cl1—O3—O4' | −101.9 (4) | O3—Cl1—O5'—O5 | −79.1 (12) |
O3'—Cl1—O3—O4' | −169.2 (10) | O6'—Cl1—O5'—O5 | 121.7 (14) |
O5'—Cl1—O3—O4' | 103.8 (2) | O3'—Cl1—O5'—O5 | −118.1 (14) |
O6—Cl1—O3—O4' | −42.9 (4) | O6—Cl1—O5'—O5 | 62.6 (15) |
O4—Cl1—O3—O4' | −162.7 (4) | O4'—Cl1—O5'—O5 | 1.7 (14) |
O5—Cl1—O4—O6' | −114.8 (7) | O4—Cl1—O5'—O5 | 172.0 (13) |
O3—Cl1—O4—O6' | 125.2 (7) | O4'—O6—O6'—O4 | 3.9 (16) |
O3'—Cl1—O4—O6' | 129.2 (4) | Cl1—O6—O6'—O4 | 6.6 (9) |
O5'—Cl1—O4—O6' | −118.4 (3) | O4'—O6—O6'—Cl1 | −2.6 (8) |
O6—Cl1—O4—O6' | 5.2 (7) | Cl1—O4—O6'—O6 | −6.6 (9) |
O4'—Cl1—O4—O6' | 27.9 (18) | O3'—O4—O6'—O6 | 32.5 (10) |
O5—Cl1—O4—O3' | 116.0 (5) | O3'—O4—O6'—Cl1 | 39.12 (18) |
O3—Cl1—O4—O3' | −4.0 (5) | O5—Cl1—O6'—O6 | −92.7 (5) |
O6'—Cl1—O4—O3' | −129.2 (4) | O3—Cl1—O6'—O6 | 86.4 (6) |
O5'—Cl1—O4—O3' | 112.44 (17) | O3'—Cl1—O6'—O6 | 122.0 (6) |
O6—Cl1—O4—O3' | −124.0 (5) | O5'—Cl1—O6'—O6 | −117.8 (6) |
O4'—Cl1—O4—O3' | −101.2 (15) | O4'—Cl1—O6'—O6 | 2.1 (6) |
O3—Cl1—O5—O5' | 111.5 (13) | O4—Cl1—O6'—O6 | 173.9 (8) |
O6'—Cl1—O5—O5' | −69.2 (13) | O5—Cl1—O6'—O4 | 93.3 (5) |
O3'—Cl1—O5—O5' | 72.7 (14) | O3—Cl1—O6'—O4 | −87.5 (6) |
O6—Cl1—O5—O5' | −128.2 (13) | O3'—Cl1—O6'—O4 | −52.0 (6) |
O4'—Cl1—O5—O5' | −178.4 (13) | O5'—Cl1—O6'—O4 | 68.3 (6) |
O4—Cl1—O5—O5' | −8.4 (13) | O6—Cl1—O6'—O4 | −173.9 (8) |
O5—Cl1—O6—O6' | 114.6 (7) | O4'—Cl1—O6'—O4 | −171.8 (6) |
Symmetry code: (i) y+1, x−1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A′···N6ii | 0.85 (3) | 1.83 (3) | 2.659 (4) | 163 (4) |
O1—H1B′···O5iii | 0.85 (4) | 1.80 (3) | 2.641 (7) | 171 (5) |
O1—H1B′···O5′iii | 0.85 (4) | 2.01 (3) | 2.855 (7) | 171 (4) |
O2—H2A···O3′iv | 0.85 (5) | 1.99 (6) | 2.821 (6) | 165 (7) |
O2—H2A···O4iv | 0.85 (5) | 2.36 (7) | 2.872 (10) | 120 (5) |
C4—H4A···O5′iv | 0.96 | 2.58 | 3.411 (7) | 145 |
C4—H4C···O6′v | 0.96 | 2.55 | 3.261 (10) | 131 |
C6—H6B···O4′vi | 0.96 | 2.24 | 3.190 (9) | 172 |
C6—H6B···O6vi | 0.96 | 2.54 | 3.342 (9) | 141 |
Symmetry codes: (ii) −x+3/2, y−1/2, −z+1/4; (iii) x+1, y−1, z; (iv) x, y−1, z; (v) y, x, −z; (vi) −x+1/2, y−1/2, −z+1/4. |
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