Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802010048/wn6100sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802010048/wn6100Isup2.hkl |
CCDC reference: 189863
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.049
- wR factor = 0.129
- Data-to-parameter ratio = 12.3
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 3 N5 -CU -N1 -C4 -179.00100.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 8 N5 -CU -N1 -C1 -5.00 4.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 21 N7 -CU -N3 -C9 -41.50 0.90 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 26 N7 -CU -N3 -C6 137.40 0.70 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 43 N1 -CU -N5 -C14 103.00 4.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 48 N1 -CU -N5 -C11 -77.00 4.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 61 N3 -CU -N7 -C19 156.10 0.70 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 66 N3 -CU -N7 -C16 -24.20 0.90 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 89 O1 -CU -O1N2-N1N2 -159.30 0.70 1.555 1.555 1.555 1.555
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
9 Alert Level C = Please check
Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO–SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELXL97 and local procedures.
[Cu(NO3)(C5H6N2)4(H2O)]NO3 | Z = 2 |
Mr = 582.05 | F(000) = 602 |
Triclinic, P1 | Dx = 1.518 Mg m−3 |
a = 8.448 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.309 (1) Å | Cell parameters from 33129 reflections |
c = 12.841 (1) Å | θ = 1.0–27.5° |
α = 88.562 (10)° | µ = 0.92 mm−1 |
β = 72.938 (10)° | T = 173 K |
γ = 86.242 (10)° | Irregular slab, blue |
V = 1273.8 (2) Å3 | 0.30 × 0.28 × 0.12 mm |
Nonius KappaCCD diffractometer | 4496 independent reflections |
Radiation source: fine-focus sealed tube | 4037 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.000 |
Detector resolution: 18 pixels mm-1 | θmax = 25.0°, θmin = 1.7° |
ω scans at fixed χ = 55° | h = −9→10 |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | k = −14→14 |
Tmin = 0.770, Tmax = 0.898 | l = −15→15 |
4496 measured reflections |
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)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.129 | w = 1/[σ2(Fo2) + (0.0643P)2 + 1.3703P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.009 |
4496 reflections | Δρmax = 1.25 e Å−3 |
366 parameters | Δρmin = −0.47 e Å−3 |
21 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0070 (17) |
Experimental. These crystals were non-merohedrally twinned. As a result, there are a lot of reflections for which Fo is significantly larger than Fc. Also the difference map is quite lumpy. Nevertheless, refinement was quite straightforward. Cu(NO3)2·2.5H2O and 2-methylpyrazine (mepyz) were purchased from commercial sources and used as received. 2-Methylpyrazine (4.70 ml, 4.84 g, 51.4 mmol) was added to a 3 ml aqueous solution of Cu(NO3)2·2.5H2O (1.00 g, 4.30 mmol). The reaction vessel was covered with parafilm in which pinholes were made to allow for slow evaporation of the solvent. Dark blue crystals of [Cu(mepyz)4(H2O)(NO3)](NO3) formed within a few days. These were isolated by decantation, mopped dry using filter paper and air-dried for less than 5 minutes. Analysis found: C, 40.79; H, 4.37; N, 23.79. C20H26CuN10O7 requires: C, 41.27; H, 4.50; N, 24.06%. Washing the product or leaving it in the open for prolonged periods of time leads to decomposition via loss of mepyz ligands. Reaction of copper(II) nitrate and a large excess of 2-methylpyrazine using ethanol containing 10% (v/v) 2,2-dimethoxypropane as the solvent leads to the precipitation of the solvated tetrakis(2-methylpyrazine) compound, Cu(mepyz)4(NO3)2·EtOH. The blue solid was isolated by vacuum filtration and dried under vacuum for about 5 minutes. Analysis found: C, 43.09; H, 5.36; N, 22.44. C22H30CuN10O7 requires: C, 43.31; H, 4.96; N, 22.96%. Cu(mepyz)4(NO3)2 (either as the water or ethanol solvate) readily looses some 2-methylpyrazine ligands and is converted to Cu(mepyz)(NO3)2 when left in open containers, whether exposed to air or an inert atmosphere. This transformation is accompanied by a color change from blue to a purple blue (periwinkle) and its completion was confirmed by elemental analysis. Analysis found: C, 21.16; H, 2.12; N, 19.69. C5H6CuN4O6 requires: C, 21.32; H, 2.15; N, 19.89%. |
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 > 2sigma(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. TwinRotMat in Ton Spek's Platon gives the following as the most likely twin law. Refinement based on the HKLF 5 format datafile produced by this program (PLATON: Spek, A.L. (1990), Acta Cryst. A46, C-34) is. 2-Rotation about (1 2 -3) [9 5 -9] Fit: 5(59) Det (-0.608 0.217 -0.391) (h1) (h2) Alpha () [] = ( 0.785 -0.565 -0.782) * (k1) = (k2) = 1.000 (-1.177 -0.652 0.173) (l1) = (l2) 0.11 Deg. The largest difference map feature (1.25eA-3) is quite close to the major component of the disordered methyl group C20. It is most likely a consequence of the trade off between modelling of twinning and/or modelling of disorder. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cu | 0.64420 (5) | 0.25714 (3) | 0.21942 (3) | 0.02371 (17) | |
O1 | 0.4299 (3) | 0.2666 (2) | 0.1458 (2) | 0.0324 (6) | |
H1O | 0.3320 | 0.2757 | 0.1822 | 0.049* | |
H2O | 0.4256 | 0.2579 | 0.0807 | 0.049* | |
N1 | 0.7949 (3) | 0.1770 (2) | 0.0869 (2) | 0.0218 (6) | |
N2 | 0.9877 (4) | 0.0816 (2) | −0.1072 (2) | 0.0271 (6) | |
C1 | 0.9568 (4) | 0.1952 (3) | 0.0462 (3) | 0.0245 (7) | |
H1 | 1.0066 | 0.2420 | 0.0836 | 0.029* | |
C2 | 1.0510 (4) | 0.1464 (3) | −0.0495 (3) | 0.0265 (7) | |
H2 | 1.1657 | 0.1593 | −0.0754 | 0.032* | |
C3 | 0.8267 (4) | 0.0643 (3) | −0.0666 (3) | 0.0254 (7) | |
C4 | 0.7319 (4) | 0.1101 (3) | 0.0314 (3) | 0.0248 (7) | |
H4 | 0.6190 | 0.0932 | 0.0597 | 0.030* | |
C5 | 0.7492 (5) | −0.0058 (3) | −0.1295 (3) | 0.0394 (9) | |
H5A | 0.8340 | −0.0331 | −0.1948 | 0.059* | |
H5B | 0.6618 | 0.0372 | −0.1508 | 0.059* | |
H5C | 0.7011 | −0.0673 | −0.0839 | 0.059* | |
N3 | 0.7265 (3) | 0.4003 (2) | 0.1509 (2) | 0.0224 (6) | |
N4 | 0.8493 (4) | 0.5952 (2) | 0.0561 (2) | 0.0310 (7) | |
C6 | 0.7134 (4) | 0.4327 (3) | 0.0528 (3) | 0.0273 (7) | |
H6 | 0.6617 | 0.3884 | 0.0143 | 0.033* | |
C7 | 0.7743 (4) | 0.5296 (3) | 0.0078 (3) | 0.0297 (8) | |
H7 | 0.7621 | 0.5506 | −0.0613 | 0.036* | |
C8 | 0.8621 (4) | 0.5631 (3) | 0.1538 (3) | 0.0269 (7) | |
C9 | 0.7998 (4) | 0.4670 (3) | 0.2015 (3) | 0.0245 (7) | |
H9 | 0.8089 | 0.4475 | 0.2717 | 0.029* | |
C10 | 0.9476 (6) | 0.6344 (4) | 0.2116 (3) | 0.0456 (10) | |
H10A | 1.0578 | 0.6490 | 0.1634 | 0.068* | |
H10B | 0.9589 | 0.5973 | 0.2777 | 0.068* | |
H10C | 0.8817 | 0.7034 | 0.2314 | 0.068* | |
N5 | 0.4991 (3) | 0.3393 (2) | 0.3525 (2) | 0.0233 (6) | |
N6 | 0.2996 (4) | 0.4526 (3) | 0.5331 (2) | 0.0324 (7) | |
C11 | 0.4967 (4) | 0.3093 (3) | 0.4540 (3) | 0.0281 (7) | |
H11 | 0.5646 | 0.2480 | 0.4647 | 0.034* | |
C12 | 0.3976 (5) | 0.3656 (3) | 0.5427 (3) | 0.0325 (8) | |
H12 | 0.3988 | 0.3420 | 0.6135 | 0.039* | |
C13 | 0.3022 (4) | 0.4840 (3) | 0.4321 (3) | 0.0306 (8) | |
C14 | 0.4016 (4) | 0.4266 (3) | 0.3422 (3) | 0.0261 (7) | |
H14 | 0.4002 | 0.4499 | 0.2713 | 0.031* | |
C15 | 0.1956 (5) | 0.5827 (4) | 0.4183 (3) | 0.0452 (10) | |
H15A | 0.0830 | 0.5615 | 0.4258 | 0.068* | |
H15B | 0.2423 | 0.6147 | 0.3460 | 0.068* | |
H15C | 0.1921 | 0.6363 | 0.4743 | 0.068* | |
N7 | 0.5889 (3) | 0.1109 (2) | 0.2939 (2) | 0.0260 (6) | |
N8 | 0.5186 (5) | −0.0896 (3) | 0.3983 (3) | 0.0405 (8) | |
C16 | 0.7094 (5) | 0.0393 (3) | 0.3059 (3) | 0.0345 (8) | |
H16 | 0.8220 | 0.0567 | 0.2774 | 0.041* | |
C17 | 0.6731 (5) | −0.0589 (3) | 0.3587 (3) | 0.0397 (9) | |
H17 | 0.753 (6) | −0.113 (4) | 0.365 (4) | 0.048* | 0.734 (10) |
C18 | 0.3985 (5) | −0.0201 (3) | 0.3825 (3) | 0.0368 (9) | |
H18 | 0.294 (11) | −0.050 (14) | 0.408 (7) | 0.044* | 0.266 (10) |
C19 | 0.4330 (4) | 0.0802 (3) | 0.3329 (3) | 0.0308 (8) | |
H19 | 0.3440 | 0.1285 | 0.3263 | 0.037* | |
C20 | 0.2206 (9) | −0.0571 (7) | 0.4210 (6) | 0.064 (2) | 0.734 (10) |
H20A | 0.2060 | −0.1106 | 0.3699 | 0.096* | 0.734 (10) |
H20B | 0.1422 | 0.0059 | 0.4242 | 0.096* | 0.734 (10) |
H20C | 0.2001 | −0.0903 | 0.4936 | 0.096* | 0.734 (10) |
C20' | 0.8181 (17) | −0.1250 (12) | 0.3812 (13) | 0.039 (4) | 0.266 (10) |
H20D | 0.7795 | −0.1635 | 0.4509 | 0.059* | 0.266 (10) |
H20E | 0.9036 | −0.0761 | 0.3844 | 0.059* | 0.266 (10) |
H20F | 0.8647 | −0.1779 | 0.3228 | 0.059* | 0.266 (10) |
N1N1 | 0.4990 (5) | 0.2680 (3) | −0.1419 (3) | 0.0449 (9) | |
O1N1 | 0.4570 (5) | 0.2531 (3) | −0.2235 (3) | 0.0727 (11) | |
O2N1 | 0.5807 (5) | 0.3479 (4) | −0.1380 (3) | 0.0775 (12) | |
O3N1 | 0.4457 (4) | 0.2086 (2) | −0.0598 (2) | 0.0472 (7) | |
N1N2 | 1.0144 (4) | 0.2613 (3) | 0.3127 (3) | 0.0345 (7) | |
O1N2 | 0.8652 (3) | 0.2490 (2) | 0.3258 (2) | 0.0409 (7) | |
O2N2 | 1.0950 (3) | 0.3149 (3) | 0.2323 (2) | 0.0471 (7) | |
O3N2 | 1.0849 (4) | 0.2263 (4) | 0.3778 (3) | 0.0866 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu | 0.0238 (2) | 0.0231 (2) | 0.0234 (2) | −0.00204 (17) | −0.00543 (17) | −0.00051 (16) |
O1 | 0.0211 (12) | 0.0475 (15) | 0.0305 (13) | −0.0010 (11) | −0.0104 (10) | −0.0047 (11) |
N1 | 0.0219 (14) | 0.0204 (14) | 0.0238 (14) | −0.0004 (11) | −0.0081 (11) | 0.0014 (11) |
N2 | 0.0295 (15) | 0.0248 (15) | 0.0266 (15) | 0.0018 (12) | −0.0079 (12) | −0.0025 (12) |
C1 | 0.0235 (17) | 0.0215 (17) | 0.0314 (18) | −0.0013 (13) | −0.0125 (14) | 0.0019 (14) |
C2 | 0.0219 (16) | 0.0225 (17) | 0.0344 (19) | −0.0016 (13) | −0.0071 (14) | 0.0032 (14) |
C3 | 0.0285 (18) | 0.0207 (17) | 0.0293 (17) | 0.0031 (14) | −0.0132 (15) | −0.0005 (13) |
C4 | 0.0194 (16) | 0.0237 (17) | 0.0329 (18) | −0.0009 (13) | −0.0103 (14) | 0.0022 (14) |
C5 | 0.041 (2) | 0.039 (2) | 0.044 (2) | 0.0003 (18) | −0.0210 (18) | −0.0118 (18) |
N3 | 0.0215 (14) | 0.0246 (14) | 0.0208 (13) | 0.0011 (11) | −0.0060 (11) | −0.0005 (11) |
N4 | 0.0352 (17) | 0.0287 (16) | 0.0295 (16) | −0.0023 (13) | −0.0104 (13) | 0.0042 (12) |
C6 | 0.0240 (17) | 0.0331 (19) | 0.0261 (17) | 0.0006 (14) | −0.0096 (14) | −0.0014 (14) |
C7 | 0.0303 (18) | 0.0330 (19) | 0.0271 (17) | 0.0034 (15) | −0.0119 (15) | 0.0063 (15) |
C8 | 0.0264 (17) | 0.0267 (18) | 0.0273 (18) | −0.0005 (14) | −0.0075 (14) | −0.0016 (14) |
C9 | 0.0244 (16) | 0.0266 (18) | 0.0231 (16) | 0.0032 (14) | −0.0089 (13) | −0.0007 (13) |
C10 | 0.059 (3) | 0.045 (2) | 0.040 (2) | −0.023 (2) | −0.021 (2) | 0.0070 (18) |
N5 | 0.0213 (14) | 0.0249 (14) | 0.0248 (14) | −0.0043 (11) | −0.0080 (11) | 0.0010 (11) |
N6 | 0.0320 (16) | 0.0369 (17) | 0.0264 (15) | 0.0014 (14) | −0.0061 (13) | −0.0015 (13) |
C11 | 0.0317 (18) | 0.0256 (18) | 0.0277 (18) | −0.0039 (15) | −0.0095 (15) | 0.0035 (14) |
C12 | 0.037 (2) | 0.035 (2) | 0.0249 (17) | −0.0042 (16) | −0.0081 (15) | 0.0043 (15) |
C13 | 0.0248 (18) | 0.037 (2) | 0.0312 (19) | 0.0016 (15) | −0.0107 (15) | −0.0030 (15) |
C14 | 0.0233 (17) | 0.0330 (19) | 0.0248 (17) | −0.0002 (15) | −0.0118 (14) | 0.0014 (14) |
C15 | 0.040 (2) | 0.055 (3) | 0.039 (2) | 0.022 (2) | −0.0137 (18) | −0.0047 (19) |
N7 | 0.0276 (15) | 0.0262 (15) | 0.0238 (14) | −0.0019 (12) | −0.0068 (12) | −0.0031 (11) |
N8 | 0.061 (2) | 0.0303 (17) | 0.0319 (17) | −0.0087 (16) | −0.0147 (16) | 0.0032 (13) |
C16 | 0.033 (2) | 0.033 (2) | 0.0340 (19) | 0.0028 (16) | −0.0050 (15) | 0.0002 (15) |
C17 | 0.052 (3) | 0.029 (2) | 0.034 (2) | 0.0074 (18) | −0.0073 (18) | 0.0022 (16) |
C18 | 0.045 (2) | 0.042 (2) | 0.0285 (19) | −0.0175 (19) | −0.0157 (17) | 0.0065 (16) |
C19 | 0.0325 (19) | 0.036 (2) | 0.0275 (18) | −0.0083 (16) | −0.0134 (15) | 0.0023 (15) |
C20 | 0.067 (5) | 0.074 (4) | 0.063 (4) | −0.039 (4) | −0.033 (3) | 0.027 (3) |
C20' | 0.037 (7) | 0.029 (7) | 0.047 (7) | 0.007 (5) | −0.007 (6) | 0.013 (6) |
N1N1 | 0.049 (2) | 0.053 (2) | 0.039 (2) | 0.0028 (18) | −0.0240 (17) | −0.0083 (17) |
O1N1 | 0.103 (3) | 0.087 (3) | 0.0427 (18) | −0.009 (2) | −0.0433 (19) | −0.0041 (17) |
O2N1 | 0.074 (2) | 0.110 (3) | 0.055 (2) | −0.043 (2) | −0.0192 (18) | −0.010 (2) |
O3N1 | 0.0506 (18) | 0.0524 (18) | 0.0418 (16) | 0.0057 (14) | −0.0208 (14) | 0.0040 (14) |
N1N2 | 0.0280 (17) | 0.0410 (19) | 0.0348 (17) | 0.0085 (14) | −0.0117 (14) | −0.0030 (14) |
O1N2 | 0.0249 (14) | 0.0478 (17) | 0.0517 (17) | −0.0040 (12) | −0.0144 (12) | 0.0096 (13) |
O2N2 | 0.0294 (14) | 0.0609 (19) | 0.0489 (17) | −0.0021 (13) | −0.0091 (13) | 0.0082 (14) |
O3N2 | 0.0431 (19) | 0.148 (4) | 0.067 (2) | 0.019 (2) | −0.0215 (18) | 0.042 (2) |
Cu—N3 | 2.021 (3) | N6—C13 | 1.338 (5) |
Cu—N7 | 2.033 (3) | C11—C12 | 1.372 (5) |
Cu—N1 | 2.034 (3) | C11—H11 | 0.9500 |
Cu—N5 | 2.035 (3) | C12—H12 | 0.9500 |
Cu—O1 | 2.271 (2) | C13—C14 | 1.390 (5) |
Cu—O1N2 | 2.613 (3) | C13—C15 | 1.502 (5) |
O1—H1O | 0.8240 | C14—H14 | 0.9500 |
O1—H2O | 0.8560 | C15—H15A | 0.9800 |
N1—C4 | 1.335 (4) | C15—H15B | 0.9800 |
N1—C1 | 1.344 (4) | C15—H15C | 0.9800 |
N2—C3 | 1.336 (4) | N7—C19 | 1.341 (4) |
N2—C2 | 1.338 (4) | N7—C16 | 1.343 (5) |
C1—C2 | 1.380 (5) | N8—C17 | 1.331 (5) |
C1—H1 | 0.9500 | N8—C18 | 1.342 (5) |
C2—H2 | 0.9500 | C16—C17 | 1.378 (5) |
C3—C4 | 1.389 (5) | C16—H16 | 0.9500 |
C3—C5 | 1.497 (5) | C17—C20' | 1.520 (12) |
C4—H4 | 0.9500 | C17—H17 | 0.94 (2) |
C5—H5A | 0.9800 | C18—C19 | 1.383 (5) |
C5—H5B | 0.9800 | C18—C20 | 1.534 (7) |
C5—H5C | 0.9800 | C18—H18 | 0.95 (2) |
N3—C9 | 1.345 (4) | C19—H19 | 0.9500 |
N3—C6 | 1.346 (4) | C20—H18 | 0.60 (6) |
N4—C7 | 1.328 (5) | C20—H20A | 0.9800 |
N4—C8 | 1.339 (4) | C20—H20B | 0.9800 |
C6—C7 | 1.376 (5) | C20—H20C | 0.9800 |
C6—H6 | 0.9500 | C20'—H17 | 0.65 (4) |
C7—H7 | 0.9500 | C20'—H20D | 0.9800 |
C8—C9 | 1.382 (5) | C20'—H20E | 0.9800 |
C8—C10 | 1.508 (5) | C20'—H20F | 0.9800 |
C9—H9 | 0.9500 | N1N1—O1N1 | 1.223 (4) |
C10—H10A | 0.9800 | N1N1—O2N1 | 1.248 (5) |
C10—H10B | 0.9800 | N1N1—O3N1 | 1.255 (4) |
C10—H10C | 0.9800 | N1N2—O3N2 | 1.217 (4) |
N5—C14 | 1.338 (4) | N1N2—O1N2 | 1.240 (4) |
N5—C11 | 1.340 (4) | N1N2—O2N2 | 1.256 (4) |
N6—C12 | 1.336 (5) | ||
N3—Cu—N7 | 172.61 (11) | C11—N5—Cu | 122.0 (2) |
N3—Cu—N1 | 89.75 (10) | C12—N6—C13 | 117.1 (3) |
N7—Cu—N1 | 88.95 (10) | N5—C11—C12 | 121.1 (3) |
N3—Cu—N5 | 89.30 (10) | N5—C11—H11 | 119.5 |
N7—Cu—N5 | 91.82 (11) | C12—C11—H11 | 119.5 |
N1—Cu—N5 | 178.36 (10) | N6—C12—C11 | 122.3 (3) |
N3—Cu—O1 | 92.44 (10) | N6—C12—H12 | 118.8 |
N7—Cu—O1 | 94.86 (11) | C11—C12—H12 | 118.8 |
N1—Cu—O1 | 91.42 (10) | N6—C13—C14 | 120.6 (3) |
N5—Cu—O1 | 89.96 (10) | N6—C13—C15 | 118.5 (3) |
N3—Cu—O1N2 | 90.10 (10) | C14—C13—C15 | 120.9 (3) |
N7—Cu—O1N2 | 82.76 (10) | N5—C14—C13 | 121.9 (3) |
N1—Cu—O1N2 | 94.63 (10) | N5—C14—H14 | 119.1 |
N5—Cu—O1N2 | 84.03 (10) | C13—C14—H14 | 119.1 |
O1—Cu—O1N2 | 173.45 (9) | C13—C15—H15A | 109.5 |
Cu—O1—H1O | 123.3 | C13—C15—H15B | 109.5 |
Cu—O1—H2O | 132.3 | H15A—C15—H15B | 109.5 |
H1O—O1—H2O | 104.2 | C13—C15—H15C | 109.5 |
C4—N1—C1 | 117.2 (3) | H15A—C15—H15C | 109.5 |
C4—N1—Cu | 120.2 (2) | H15B—C15—H15C | 109.5 |
C1—N1—Cu | 122.4 (2) | C19—N7—C16 | 116.4 (3) |
C3—N2—C2 | 116.5 (3) | C19—N7—Cu | 122.7 (2) |
N1—C1—C2 | 120.4 (3) | C16—N7—Cu | 120.9 (2) |
N1—C1—H1 | 119.8 | C17—N8—C18 | 116.2 (3) |
C2—C1—H1 | 119.8 | N7—C16—C17 | 121.3 (4) |
N2—C2—C1 | 122.8 (3) | N7—C16—H16 | 119.3 |
N2—C2—H2 | 118.6 | C17—C16—H16 | 119.3 |
C1—C2—H2 | 118.6 | N8—C17—C16 | 122.5 (4) |
N2—C3—C4 | 121.2 (3) | N8—C17—C20' | 121.1 (7) |
N2—C3—C5 | 118.5 (3) | C16—C17—C20' | 116.0 (7) |
C4—C3—C5 | 120.2 (3) | N8—C17—H17 | 113 (4) |
N1—C4—C3 | 121.8 (3) | C16—C17—H17 | 124 (4) |
N1—C4—H4 | 119.1 | C20'—C17—H17 | 14 (4) |
C3—C4—H4 | 119.1 | N8—C18—C19 | 121.7 (3) |
C3—C5—H5A | 109.5 | N8—C18—C20 | 117.1 (4) |
C3—C5—H5B | 109.5 | C19—C18—C20 | 121.2 (4) |
H5A—C5—H5B | 109.5 | N8—C18—H18 | 111 (10) |
C3—C5—H5C | 109.5 | C19—C18—H18 | 127 (10) |
H5A—C5—H5C | 109.5 | C20—C18—H18 | 6 (10) |
H5B—C5—H5C | 109.5 | N7—C19—C18 | 121.7 (3) |
C9—N3—C6 | 116.9 (3) | N7—C19—H19 | 119.2 |
C9—N3—Cu | 121.0 (2) | C18—C19—H19 | 119.2 |
C6—N3—Cu | 122.1 (2) | C18—C20—H18 | 10 (10) |
C7—N4—C8 | 116.4 (3) | C18—C20—H20A | 109.5 |
N3—C6—C7 | 120.4 (3) | C18—C20—H20B | 109.5 |
N3—C6—H6 | 119.8 | C18—C20—H20C | 109.5 |
C7—C6—H6 | 119.8 | C17—C20'—H17 | 20 (5) |
N4—C7—C6 | 123.2 (3) | C17—C20'—H20D | 109.5 |
N4—C7—H7 | 118.4 | H17—C20'—H20D | 106.1 |
C6—C7—H7 | 118.4 | C17—C20'—H20E | 109.5 |
N4—C8—C9 | 121.5 (3) | H17—C20'—H20E | 127.5 |
N4—C8—C10 | 118.4 (3) | H20D—C20'—H20E | 109.5 |
C9—C8—C10 | 120.1 (3) | C17—C20'—H20F | 109.5 |
N3—C9—C8 | 121.6 (3) | H17—C20'—H20F | 93.1 |
N3—C9—H9 | 119.2 | H20D—C20'—H20F | 109.5 |
C8—C9—H9 | 119.2 | H20E—C20'—H20F | 109.5 |
C8—C10—H10A | 109.5 | O1N1—N1N1—O2N1 | 119.5 (4) |
C8—C10—H10B | 109.5 | O1N1—N1N1—O3N1 | 119.1 (4) |
H10A—C10—H10B | 109.5 | O2N1—N1N1—O3N1 | 121.0 (3) |
C8—C10—H10C | 109.5 | O3N2—N1N2—O1N2 | 122.1 (3) |
H10A—C10—H10C | 109.5 | O3N2—N1N2—O2N2 | 118.2 (3) |
H10B—C10—H10C | 109.5 | O1N2—N1N2—O2N2 | 119.7 (3) |
C14—N5—C11 | 117.0 (3) | N1N2—O1N2—Cu | 141.5 (2) |
C14—N5—Cu | 121.0 (2) | ||
N3—Cu—N1—C4 | −124.6 (2) | N3—Cu—N5—C11 | −131.2 (3) |
N7—Cu—N1—C4 | 62.7 (2) | N7—Cu—N5—C11 | 41.5 (3) |
N5—Cu—N1—C4 | −179 (100) | N1—Cu—N5—C11 | −77 (4) |
O1—Cu—N1—C4 | −32.1 (2) | O1—Cu—N5—C11 | 136.4 (3) |
O1N2—Cu—N1—C4 | 145.4 (2) | O1N2—Cu—N5—C11 | −41.0 (3) |
N3—Cu—N1—C1 | 49.9 (3) | C14—N5—C11—C12 | 0.3 (5) |
N7—Cu—N1—C1 | −122.8 (3) | Cu—N5—C11—C12 | −179.8 (3) |
N5—Cu—N1—C1 | −5 (4) | C13—N6—C12—C11 | −0.5 (5) |
O1—Cu—N1—C1 | 142.3 (3) | N5—C11—C12—N6 | −0.1 (5) |
O1N2—Cu—N1—C1 | −40.2 (3) | C12—N6—C13—C14 | 1.0 (5) |
C4—N1—C1—C2 | 0.5 (5) | C12—N6—C13—C15 | −179.0 (3) |
Cu—N1—C1—C2 | −174.2 (2) | C11—N5—C14—C13 | 0.2 (5) |
C3—N2—C2—C1 | −1.2 (5) | Cu—N5—C14—C13 | −179.7 (2) |
N1—C1—C2—N2 | 1.5 (5) | N6—C13—C14—N5 | −0.8 (5) |
C2—N2—C3—C4 | −1.0 (5) | C15—C13—C14—N5 | 179.1 (3) |
C2—N2—C3—C5 | 178.8 (3) | N3—Cu—N7—C19 | 156.1 (7) |
C1—N1—C4—C3 | −2.7 (5) | N1—Cu—N7—C19 | −124.0 (3) |
Cu—N1—C4—C3 | 172.1 (2) | N5—Cu—N7—C19 | 57.5 (3) |
N2—C3—C4—N1 | 3.1 (5) | O1—Cu—N7—C19 | −32.6 (3) |
C5—C3—C4—N1 | −176.7 (3) | O1N2—Cu—N7—C19 | 141.2 (3) |
N7—Cu—N3—C9 | −41.5 (9) | N3—Cu—N7—C16 | −24.2 (9) |
N1—Cu—N3—C9 | −121.4 (2) | N1—Cu—N7—C16 | 55.7 (3) |
N5—Cu—N3—C9 | 57.3 (2) | N5—Cu—N7—C16 | −122.8 (3) |
O1—Cu—N3—C9 | 147.2 (2) | O1—Cu—N7—C16 | 147.1 (3) |
O1N2—Cu—N3—C9 | −26.7 (2) | O1N2—Cu—N7—C16 | −39.1 (3) |
N7—Cu—N3—C6 | 137.4 (7) | C19—N7—C16—C17 | −2.0 (5) |
N1—Cu—N3—C6 | 57.5 (2) | Cu—N7—C16—C17 | 178.3 (3) |
N5—Cu—N3—C6 | −123.8 (3) | C18—N8—C17—C16 | 1.0 (5) |
O1—Cu—N3—C6 | −33.9 (2) | C18—N8—C17—C20' | 173.7 (8) |
O1N2—Cu—N3—C6 | 152.2 (2) | N7—C16—C17—N8 | 1.6 (6) |
C9—N3—C6—C7 | 0.4 (5) | N7—C16—C17—C20' | −171.4 (7) |
Cu—N3—C6—C7 | −178.5 (2) | C17—N8—C18—C19 | −3.2 (5) |
C8—N4—C7—C6 | −0.8 (5) | C17—N8—C18—C20 | 176.2 (4) |
N3—C6—C7—N4 | 0.7 (5) | C16—N7—C19—C18 | −0.2 (5) |
C7—N4—C8—C9 | −0.2 (5) | Cu—N7—C19—C18 | 179.5 (3) |
C7—N4—C8—C10 | 179.5 (3) | N8—C18—C19—N7 | 2.9 (5) |
C6—N3—C9—C8 | −1.4 (4) | C20—C18—C19—N7 | −176.5 (4) |
Cu—N3—C9—C8 | 177.6 (2) | O3N2—N1N2—O1N2—Cu | −162.7 (4) |
N4—C8—C9—N3 | 1.4 (5) | O2N2—N1N2—O1N2—Cu | 20.2 (6) |
C10—C8—C9—N3 | −178.4 (3) | N3—Cu—O1N2—N1N2 | −46.5 (4) |
N3—Cu—N5—C14 | 48.7 (3) | N7—Cu—O1N2—N1N2 | 131.6 (4) |
N7—Cu—N5—C14 | −138.6 (2) | N1—Cu—O1N2—N1N2 | 43.3 (4) |
N1—Cu—N5—C14 | 103 (4) | N5—Cu—O1N2—N1N2 | −135.7 (4) |
O1—Cu—N5—C14 | −43.7 (2) | O1—Cu—O1N2—N1N2 | −159.3 (7) |
O1N2—Cu—N5—C14 | 138.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O2N2i | 0.82 | 1.94 | 2.746 (5) | 164 |
O1—H2O···O3N1 | 0.86 | 1.88 | 2.719 (5) | 167 |
Symmetry code: (i) x−1, y, z. |
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