Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806016333/ww2013sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806016333/ww2013Isup2.hkl |
CCDC reference: 610926
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
[Cu(C4H6N2)(C6H18N4)](ClO4)2 | F(000) = 2024 |
Mr = 490.80 | Dx = 1.709 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 9198 reflections |
a = 21.9941 (7) Å | θ = 0.9–28.0° |
b = 7.8942 (3) Å | µ = 1.48 mm−1 |
c = 21.9941 (7) Å | T = 100 K |
β = 92.607 (2)° | Needle, blue |
V = 3814.8 (2) Å3 | 0.43 × 0.13 × 0.10 mm |
Z = 8 |
Bruker SMART APEX2 CCD area-detector diffractometer | 9198 independent reflections |
Radiation source: fine-focus sealed tube | 7032 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.0°, θmin = 0.9° |
ω scans | h = −29→29 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −10→10 |
Tmin = 0.794, Tmax = 0.863 | l = −29→29 |
41516 measured reflections |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0788P)2] where P = (Fo2 + 2Fc2)/3 |
9198 reflections | (Δ/σ)max = 0.001 |
482 parameters | Δρmax = 0.89 e Å−3 |
0 restraints | Δρmin = −1.04 e Å−3 |
Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment |
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 > 2σ(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 | ||
Cu1 | 0.80503 (3) | 0.28293 (7) | 0.09078 (3) | 0.01641 (16) | |
Cu2 | 0.41389 (3) | 0.26543 (11) | 0.19407 (3) | 0.01780 (16) | |
Cl1 | 0.58046 (5) | −0.20466 (15) | 0.16556 (5) | 0.0186 (3) | |
Cl2 | 0.18146 (7) | 0.2578 (2) | 0.37160 (7) | 0.0307 (3) | |
Cl3 | 0.62822 (6) | 0.30378 (16) | 0.32509 (6) | 0.0283 (3) | |
Cl4 | 0.16773 (6) | 0.23126 (18) | 0.08051 (6) | 0.0207 (3)* | |
O1 | 0.64587 (16) | −0.1984 (5) | 0.16405 (18) | 0.0268 (9) | |
O2 | 0.55809 (16) | −0.3546 (5) | 0.13348 (16) | 0.0267 (8) | |
O3 | 0.55468 (16) | −0.0559 (5) | 0.13609 (15) | 0.0271 (8) | |
O4 | 0.56218 (17) | −0.2102 (5) | 0.22727 (17) | 0.0278 (9) | |
O5 | 0.1227 (2) | 0.1779 (6) | 0.3626 (3) | 0.0656 (15) | |
O6 | 0.1869 (3) | 0.3179 (7) | 0.4322 (2) | 0.0692 (16) | |
O7 | 0.18419 (19) | 0.3978 (6) | 0.33091 (18) | 0.0483 (11) | |
O8 | 0.2287 (2) | 0.1380 (5) | 0.3602 (2) | 0.0553 (13) | |
O9 | 0.6139 (3) | 0.3699 (7) | 0.3828 (2) | 0.0781 (17) | |
O10 | 0.6379 (2) | 0.4376 (5) | 0.2838 (2) | 0.0668 (15) | |
O11 | 0.6813 (2) | 0.2039 (6) | 0.3305 (2) | 0.0616 (15) | |
O12 | 0.5788 (3) | 0.2029 (8) | 0.3036 (3) | 0.094 (2) | |
O13 | 0.14142 (16) | 0.3815 (5) | 0.05278 (16) | 0.0327 (9) | |
O14 | 0.13402 (16) | 0.0836 (5) | 0.05867 (16) | 0.0327 (9) | |
O15 | 0.1641 (2) | 0.2437 (5) | 0.14492 (17) | 0.0296 (9) | |
O16 | 0.23062 (16) | 0.2167 (5) | 0.06429 (17) | 0.0249 (9) | |
N1 | 0.71605 (19) | 0.2604 (5) | 0.11379 (19) | 0.0176 (9) | |
N2 | 0.77521 (18) | 0.5185 (5) | 0.0519 (2) | 0.0279 (10) | |
H2C | 0.7873 | 0.6054 | 0.0760 | 0.033* | |
H2D | 0.7906 | 0.5331 | 0.0151 | 0.033* | |
N3 | 0.78554 (19) | 0.0692 (6) | 0.0397 (2) | 0.0354 (12) | |
H3C | 0.7792 | 0.0972 | 0.0003 | 0.042* | |
H3D | 0.8169 | −0.0039 | 0.0429 | 0.042* | |
N4 | 0.8237 (2) | 0.3013 (6) | 0.1829 (2) | 0.0285 (11) | |
H4C | 0.8447 | 0.2095 | 0.1961 | 0.034* | |
H4D | 0.8467 | 0.3936 | 0.1910 | 0.034* | |
N5 | 0.89156 (19) | 0.2943 (5) | 0.0689 (2) | 0.0226 (10) | |
N6 | 0.9739 (2) | 0.2658 (6) | 0.0164 (2) | 0.0277 (11) | |
N7 | 0.38823 (18) | 0.2918 (5) | 0.28151 (19) | 0.0175 (9) | |
N8 | 0.4409 (2) | 0.0183 (5) | 0.22279 (18) | 0.0256 (10) | |
H8B | 0.4155 | −0.0596 | 0.2059 | 0.031* | |
H8C | 0.4788 | −0.0039 | 0.2113 | 0.031* | |
N9 | 0.3215 (2) | 0.2883 (6) | 0.1731 (2) | 0.0257 (10) | |
H9B | 0.3144 | 0.3839 | 0.1517 | 0.031* | |
H9C | 0.3088 | 0.2000 | 0.1499 | 0.031* | |
N10 | 0.4810 (2) | 0.4414 (6) | 0.22050 (18) | 0.0350 (11) | |
H10D | 0.5162 | 0.3885 | 0.2307 | 0.042* | |
H10E | 0.4874 | 0.5143 | 0.1900 | 0.042* | |
N11 | 0.4380 (2) | 0.2445 (5) | 0.1085 (2) | 0.0216 (10) | |
N12 | 0.4906 (2) | 0.2548 (5) | 0.0264 (2) | 0.0245 (10) | |
C1 | 0.6860 (2) | 0.4279 (6) | 0.1039 (2) | 0.0254 (11) | |
H1A | 0.6954 | 0.5010 | 0.1384 | 0.030* | |
H1B | 0.6422 | 0.4129 | 0.1004 | 0.030* | |
C2 | 0.7077 (2) | 0.5095 (7) | 0.0465 (3) | 0.0311 (13) | |
H2A | 0.6948 | 0.4428 | 0.0112 | 0.037* | |
H2B | 0.6907 | 0.6224 | 0.0419 | 0.037* | |
C3 | 0.6854 (2) | 0.1307 (6) | 0.0752 (2) | 0.0214 (10) | |
H3A | 0.6706 | 0.1809 | 0.0371 | 0.026* | |
H3B | 0.6509 | 0.0845 | 0.0956 | 0.026* | |
C4 | 0.7306 (2) | −0.0091 (6) | 0.0629 (2) | 0.0265 (12) | |
H4A | 0.7407 | −0.0710 | 0.1001 | 0.032* | |
H4B | 0.7130 | −0.0879 | 0.0331 | 0.032* | |
C5 | 0.7169 (2) | 0.2113 (7) | 0.1787 (2) | 0.0251 (11) | |
H5A | 0.7259 | 0.0915 | 0.1827 | 0.030* | |
H5B | 0.6772 | 0.2318 | 0.1948 | 0.030* | |
C6 | 0.7651 (2) | 0.3140 (8) | 0.2147 (2) | 0.0325 (14) | |
H6A | 0.7525 | 0.4315 | 0.2172 | 0.039* | |
H6B | 0.7704 | 0.2697 | 0.2558 | 0.039* | |
C7 | 0.9133 (2) | 0.2554 (8) | 0.0160 (3) | 0.0356 (16) | |
H7A | 0.8892 | 0.2241 | −0.0180 | 0.043* | |
C8 | 0.9927 (3) | 0.3164 (9) | 0.0729 (3) | 0.0485 (18) | |
H8A | 1.0325 | 0.3367 | 0.0870 | 0.058* | |
C9 | 0.9418 (3) | 0.3317 (9) | 0.1047 (3) | 0.0488 (18) | |
H9A | 0.9412 | 0.3634 | 0.1454 | 0.059* | |
C10 | 1.0134 (3) | 0.2264 (10) | −0.0334 (3) | 0.055 (2) | |
H10A | 0.9889 | 0.1933 | −0.0687 | 0.083* | |
H10B | 1.0403 | 0.1354 | −0.0215 | 0.083* | |
H10C | 1.0368 | 0.3248 | −0.0429 | 0.083* | |
C11 | 0.3859 (2) | 0.1196 (6) | 0.3085 (2) | 0.0242 (11) | |
H11A | 0.3480 | 0.0651 | 0.2955 | 0.029* | |
H11B | 0.3871 | 0.1285 | 0.3525 | 0.029* | |
C12 | 0.4389 (2) | 0.0126 (7) | 0.2893 (2) | 0.0267 (12) | |
H12A | 0.4767 | 0.0562 | 0.3077 | 0.032* | |
H12B | 0.4339 | −0.1034 | 0.3027 | 0.032* | |
C13 | 0.3266 (2) | 0.3730 (7) | 0.2784 (2) | 0.0273 (12) | |
H13A | 0.3306 | 0.4933 | 0.2706 | 0.033* | |
H13B | 0.3075 | 0.3590 | 0.3169 | 0.033* | |
C14 | 0.2876 (2) | 0.2927 (8) | 0.2283 (3) | 0.0286 (13) | |
H14A | 0.2765 | 0.1785 | 0.2398 | 0.034* | |
H14B | 0.2505 | 0.3577 | 0.2213 | 0.034* | |
C15 | 0.4332 (2) | 0.3996 (6) | 0.3155 (2) | 0.0232 (11) | |
H15A | 0.4663 | 0.3300 | 0.3320 | 0.028* | |
H15B | 0.4139 | 0.4540 | 0.3492 | 0.028* | |
C16 | 0.4579 (3) | 0.5327 (7) | 0.2739 (2) | 0.0323 (13) | |
H16A | 0.4260 | 0.6116 | 0.2611 | 0.039* | |
H16B | 0.4905 | 0.5955 | 0.2948 | 0.039* | |
C17 | 0.4896 (3) | 0.2921 (7) | 0.0857 (2) | 0.0269 (13) | |
H17A | 0.5212 | 0.3448 | 0.1079 | 0.032* | |
C18 | 0.4376 (3) | 0.1752 (8) | 0.0108 (3) | 0.0399 (15) | |
H18A | 0.4256 | 0.1331 | −0.0274 | 0.048* | |
C19 | 0.4056 (3) | 0.1689 (9) | 0.0618 (3) | 0.0465 (17) | |
H19A | 0.3673 | 0.1203 | 0.0646 | 0.056* | |
C20 | 0.5413 (3) | 0.2914 (8) | −0.0136 (3) | 0.0348 (15) | |
H20A | 0.5727 | 0.3519 | 0.0091 | 0.052* | |
H20B | 0.5266 | 0.3592 | −0.0474 | 0.052* | |
H20C | 0.5574 | 0.1870 | −0.0283 | 0.052* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0163 (3) | 0.0151 (3) | 0.0180 (3) | −0.0007 (2) | 0.0019 (2) | 0.0002 (2) |
Cu2 | 0.0215 (3) | 0.0164 (4) | 0.0157 (3) | 0.0001 (3) | 0.0030 (2) | −0.0002 (2) |
Cl1 | 0.0168 (5) | 0.0175 (6) | 0.0218 (6) | −0.0009 (5) | 0.0032 (4) | 0.0007 (5) |
Cl2 | 0.0419 (8) | 0.0229 (6) | 0.0283 (7) | −0.0007 (6) | 0.0136 (6) | 0.0002 (6) |
Cl3 | 0.0256 (7) | 0.0231 (7) | 0.0369 (7) | −0.0009 (6) | 0.0087 (5) | −0.0026 (6) |
O1 | 0.0170 (18) | 0.028 (2) | 0.036 (2) | −0.0007 (17) | 0.0058 (15) | −0.0003 (18) |
O2 | 0.0280 (19) | 0.0226 (19) | 0.0297 (19) | −0.0096 (17) | 0.0037 (15) | −0.0045 (17) |
O3 | 0.0311 (19) | 0.0222 (19) | 0.0283 (19) | 0.0076 (17) | 0.0053 (15) | 0.0056 (16) |
O4 | 0.028 (2) | 0.033 (2) | 0.023 (2) | −0.0003 (17) | 0.0037 (15) | 0.0014 (17) |
O5 | 0.049 (3) | 0.048 (3) | 0.102 (4) | −0.013 (3) | 0.031 (3) | −0.014 (3) |
O6 | 0.102 (4) | 0.076 (4) | 0.031 (2) | 0.009 (3) | 0.006 (2) | −0.010 (3) |
O7 | 0.050 (3) | 0.051 (3) | 0.045 (2) | 0.009 (2) | 0.011 (2) | 0.021 (2) |
O8 | 0.061 (3) | 0.029 (2) | 0.079 (3) | 0.003 (2) | 0.031 (2) | −0.001 (2) |
O9 | 0.108 (4) | 0.077 (4) | 0.053 (3) | −0.011 (4) | 0.050 (3) | −0.018 (3) |
O10 | 0.114 (4) | 0.026 (2) | 0.064 (3) | 0.009 (3) | 0.040 (3) | 0.014 (2) |
O11 | 0.055 (3) | 0.072 (4) | 0.059 (3) | 0.036 (3) | 0.018 (2) | 0.028 (3) |
O12 | 0.047 (3) | 0.121 (5) | 0.113 (5) | −0.050 (4) | 0.000 (3) | −0.025 (4) |
O13 | 0.031 (2) | 0.032 (2) | 0.035 (2) | 0.0059 (18) | 0.0025 (16) | 0.0162 (19) |
O14 | 0.034 (2) | 0.034 (2) | 0.031 (2) | −0.0155 (19) | 0.0068 (16) | −0.0086 (18) |
O15 | 0.042 (2) | 0.030 (2) | 0.0168 (19) | −0.0006 (18) | 0.0050 (16) | −0.0027 (16) |
O16 | 0.0183 (18) | 0.032 (2) | 0.025 (2) | 0.0004 (16) | 0.0035 (14) | −0.0042 (17) |
N1 | 0.020 (2) | 0.015 (2) | 0.018 (2) | 0.0041 (17) | 0.0001 (16) | −0.0013 (17) |
N2 | 0.029 (2) | 0.022 (2) | 0.033 (2) | −0.001 (2) | 0.0031 (18) | 0.006 (2) |
N3 | 0.025 (2) | 0.030 (3) | 0.052 (3) | −0.007 (2) | 0.014 (2) | −0.016 (2) |
N4 | 0.023 (2) | 0.037 (3) | 0.025 (2) | −0.006 (2) | 0.0004 (18) | 0.001 (2) |
N5 | 0.019 (2) | 0.019 (2) | 0.030 (2) | −0.0026 (19) | 0.0048 (17) | −0.002 (2) |
N6 | 0.022 (2) | 0.040 (3) | 0.022 (2) | −0.005 (2) | 0.0086 (18) | −0.002 (2) |
N7 | 0.017 (2) | 0.015 (2) | 0.020 (2) | −0.0027 (17) | 0.0040 (16) | −0.0006 (17) |
N8 | 0.035 (2) | 0.019 (2) | 0.023 (2) | 0.007 (2) | 0.0051 (17) | −0.0011 (19) |
N9 | 0.028 (2) | 0.026 (2) | 0.022 (2) | 0.005 (2) | −0.0049 (18) | −0.001 (2) |
N10 | 0.046 (3) | 0.035 (3) | 0.024 (2) | −0.016 (2) | 0.0068 (19) | −0.002 (2) |
N11 | 0.028 (2) | 0.018 (2) | 0.019 (2) | −0.0035 (18) | 0.0020 (17) | −0.0003 (17) |
N12 | 0.031 (3) | 0.025 (2) | 0.017 (2) | 0.006 (2) | 0.0032 (18) | 0.0005 (19) |
C1 | 0.020 (2) | 0.018 (3) | 0.038 (3) | 0.007 (2) | 0.003 (2) | −0.004 (2) |
C2 | 0.027 (3) | 0.016 (3) | 0.050 (3) | 0.004 (2) | −0.008 (2) | 0.006 (3) |
C3 | 0.023 (2) | 0.015 (2) | 0.026 (3) | −0.008 (2) | 0.0003 (19) | −0.003 (2) |
C4 | 0.030 (3) | 0.013 (2) | 0.036 (3) | −0.008 (2) | 0.006 (2) | −0.007 (2) |
C5 | 0.024 (3) | 0.035 (3) | 0.016 (2) | −0.004 (2) | 0.0052 (18) | 0.004 (2) |
C6 | 0.029 (3) | 0.054 (4) | 0.015 (3) | −0.007 (3) | 0.004 (2) | −0.004 (3) |
C7 | 0.019 (3) | 0.068 (4) | 0.020 (3) | −0.007 (3) | 0.000 (2) | −0.001 (3) |
C8 | 0.018 (3) | 0.084 (5) | 0.043 (4) | −0.004 (3) | 0.000 (2) | −0.020 (4) |
C9 | 0.030 (3) | 0.085 (5) | 0.032 (3) | −0.013 (3) | 0.007 (2) | −0.030 (3) |
C10 | 0.022 (3) | 0.125 (7) | 0.020 (3) | −0.004 (3) | 0.006 (2) | −0.016 (3) |
C11 | 0.031 (3) | 0.019 (3) | 0.023 (2) | −0.003 (2) | 0.003 (2) | −0.001 (2) |
C12 | 0.033 (3) | 0.019 (3) | 0.028 (3) | 0.000 (2) | −0.006 (2) | 0.002 (2) |
C13 | 0.029 (3) | 0.026 (3) | 0.027 (3) | 0.013 (2) | 0.006 (2) | −0.003 (2) |
C14 | 0.023 (3) | 0.035 (3) | 0.028 (3) | 0.004 (3) | 0.003 (2) | −0.005 (3) |
C15 | 0.030 (3) | 0.019 (2) | 0.020 (2) | −0.001 (2) | 0.0009 (19) | −0.005 (2) |
C16 | 0.051 (4) | 0.021 (3) | 0.024 (3) | −0.016 (3) | 0.000 (2) | −0.009 (2) |
C17 | 0.025 (3) | 0.033 (3) | 0.023 (3) | 0.004 (2) | 0.001 (2) | 0.000 (2) |
C18 | 0.050 (4) | 0.045 (4) | 0.025 (3) | −0.025 (3) | 0.007 (2) | −0.011 (3) |
C19 | 0.055 (4) | 0.061 (4) | 0.025 (3) | −0.036 (4) | 0.007 (3) | −0.004 (3) |
C20 | 0.034 (3) | 0.047 (4) | 0.024 (3) | 0.004 (3) | 0.009 (2) | 0.003 (3) |
Cu1—N5 | 1.986 (4) | N10—C16 | 1.488 (7) |
Cu1—N1 | 2.051 (4) | N10—H10D | 0.9000 |
Cu1—N4 | 2.053 (5) | N10—H10E | 0.9000 |
Cu1—N3 | 2.061 (5) | N11—C17 | 1.315 (7) |
Cu1—N2 | 2.138 (4) | N11—C19 | 1.360 (7) |
Cu2—N11 | 1.985 (4) | N12—C17 | 1.338 (7) |
Cu2—N7 | 2.039 (4) | N12—C18 | 1.355 (7) |
Cu2—N9 | 2.071 (4) | N12—C20 | 1.478 (7) |
Cu2—N10 | 2.090 (4) | C1—C2 | 1.512 (7) |
Cu2—N8 | 2.127 (4) | C1—H1A | 0.9700 |
Cl1—O4 | 1.434 (4) | C1—H1B | 0.9700 |
Cl1—O1 | 1.441 (4) | C2—H2A | 0.9700 |
Cl1—O3 | 1.445 (4) | C2—H2B | 0.9700 |
Cl1—O2 | 1.453 (4) | C3—C4 | 1.517 (7) |
Cl2—O6 | 1.414 (5) | C3—H3A | 0.9700 |
Cl2—O7 | 1.425 (4) | C3—H3B | 0.9700 |
Cl2—O8 | 1.435 (4) | C4—H4A | 0.9700 |
Cl2—O5 | 1.444 (5) | C4—H4B | 0.9700 |
Cl3—O11 | 1.409 (4) | C5—C6 | 1.527 (7) |
Cl3—O12 | 1.411 (5) | C5—H5A | 0.9700 |
Cl3—O10 | 1.416 (4) | C5—H5B | 0.9700 |
Cl3—O9 | 1.420 (5) | C6—H6A | 0.9700 |
Cl4—O15 | 1.426 (4) | C6—H6B | 0.9700 |
Cl4—O13 | 1.443 (4) | C7—H7A | 0.9300 |
Cl4—O16 | 1.449 (4) | C8—C9 | 1.351 (8) |
Cl4—O14 | 1.452 (4) | C8—H8A | 0.9300 |
N1—C3 | 1.473 (6) | C9—H9A | 0.9300 |
N1—C5 | 1.478 (6) | C10—H10A | 0.9600 |
N1—C1 | 1.490 (6) | C10—H10B | 0.9600 |
N2—C2 | 1.486 (6) | C10—H10C | 0.9600 |
N2—H2C | 0.9000 | C11—C12 | 1.516 (7) |
N2—H2D | 0.9000 | C11—H11A | 0.9700 |
N3—C4 | 1.470 (6) | C11—H11B | 0.9700 |
N3—H3C | 0.9000 | C12—H12A | 0.9700 |
N3—H3D | 0.9000 | C12—H12B | 0.9700 |
N4—C6 | 1.499 (7) | C13—C14 | 1.505 (7) |
N4—H4C | 0.9000 | C13—H13A | 0.9700 |
N4—H4D | 0.9000 | C13—H13B | 0.9700 |
N5—C7 | 1.314 (7) | C14—H14A | 0.9700 |
N5—C9 | 1.360 (7) | C14—H14B | 0.9700 |
N6—C7 | 1.335 (7) | C15—C16 | 1.511 (7) |
N6—C8 | 1.352 (7) | C15—H15A | 0.9700 |
N6—C10 | 1.462 (7) | C15—H15B | 0.9700 |
N7—C15 | 1.481 (6) | C16—H16A | 0.9700 |
N7—C11 | 1.485 (6) | C16—H16B | 0.9700 |
N7—C13 | 1.499 (6) | C17—H17A | 0.9300 |
N8—C12 | 1.466 (6) | C18—C19 | 1.353 (8) |
N8—H8B | 0.9000 | C18—H18A | 0.9300 |
N8—H8C | 0.9000 | C19—H19A | 0.9300 |
N9—C14 | 1.453 (7) | C20—H20A | 0.9600 |
N9—H9B | 0.9000 | C20—H20B | 0.9600 |
N9—H9C | 0.9000 | C20—H20C | 0.9600 |
N5—Cu1—N1 | 177.58 (17) | C18—N12—C20 | 127.1 (5) |
N5—Cu1—N4 | 94.85 (18) | N1—C1—C2 | 110.2 (4) |
N1—Cu1—N4 | 85.04 (17) | N1—C1—H1A | 109.6 |
N5—Cu1—N3 | 94.74 (17) | C2—C1—H1A | 109.6 |
N1—Cu1—N3 | 83.47 (16) | N1—C1—H1B | 109.6 |
N4—Cu1—N3 | 128.5 (2) | C2—C1—H1B | 109.6 |
N5—Cu1—N2 | 98.27 (17) | H1A—C1—H1B | 108.1 |
N1—Cu1—N2 | 84.00 (16) | N2—C2—C1 | 107.8 (4) |
N4—Cu1—N2 | 112.15 (18) | N2—C2—H2A | 110.1 |
N3—Cu1—N2 | 116.23 (19) | C1—C2—H2A | 110.1 |
N11—Cu2—N7 | 178.76 (17) | N2—C2—H2B | 110.1 |
N11—Cu2—N9 | 95.63 (18) | C1—C2—H2B | 110.1 |
N7—Cu2—N9 | 83.68 (17) | H2A—C2—H2B | 108.5 |
N11—Cu2—N10 | 95.92 (17) | N1—C3—C4 | 108.8 (4) |
N7—Cu2—N10 | 83.81 (16) | N1—C3—H3A | 109.9 |
N9—Cu2—N10 | 132.62 (19) | C4—C3—H3A | 109.9 |
N11—Cu2—N8 | 97.02 (16) | N1—C3—H3B | 109.9 |
N7—Cu2—N8 | 84.20 (16) | C4—C3—H3B | 109.9 |
N9—Cu2—N8 | 113.82 (17) | H3A—C3—H3B | 108.3 |
N10—Cu2—N8 | 110.07 (18) | N3—C4—C3 | 108.1 (4) |
O4—Cl1—O1 | 110.2 (2) | N3—C4—H4A | 110.1 |
O4—Cl1—O3 | 109.2 (2) | C3—C4—H4A | 110.1 |
O1—Cl1—O3 | 109.5 (2) | N3—C4—H4B | 110.1 |
O4—Cl1—O2 | 109.3 (2) | C3—C4—H4B | 110.1 |
O1—Cl1—O2 | 109.5 (2) | H4A—C4—H4B | 108.4 |
O3—Cl1—O2 | 109.1 (2) | N1—C5—C6 | 109.9 (4) |
O6—Cl2—O7 | 109.1 (3) | N1—C5—H5A | 109.7 |
O6—Cl2—O8 | 110.8 (3) | C6—C5—H5A | 109.7 |
O7—Cl2—O8 | 110.5 (3) | N1—C5—H5B | 109.7 |
O6—Cl2—O5 | 108.2 (3) | C6—C5—H5B | 109.7 |
O7—Cl2—O5 | 108.4 (3) | H5A—C5—H5B | 108.2 |
O8—Cl2—O5 | 109.8 (3) | N4—C6—C5 | 108.3 (4) |
O11—Cl3—O12 | 109.6 (4) | N4—C6—H6A | 110.0 |
O11—Cl3—O10 | 108.8 (3) | C5—C6—H6A | 110.0 |
O12—Cl3—O10 | 110.0 (4) | N4—C6—H6B | 110.0 |
O11—Cl3—O9 | 110.3 (3) | C5—C6—H6B | 110.0 |
O12—Cl3—O9 | 107.9 (4) | H6A—C6—H6B | 108.4 |
O10—Cl3—O9 | 110.2 (3) | N5—C7—N6 | 112.5 (5) |
O15—Cl4—O13 | 108.9 (2) | N5—C7—H7A | 123.7 |
O15—Cl4—O16 | 110.3 (2) | N6—C7—H7A | 123.7 |
O13—Cl4—O16 | 109.3 (2) | C9—C8—N6 | 106.1 (5) |
O15—Cl4—O14 | 109.5 (2) | C9—C8—H8A | 127.0 |
O13—Cl4—O14 | 109.3 (2) | N6—C8—H8A | 127.0 |
O16—Cl4—O14 | 109.5 (2) | C8—C9—N5 | 110.6 (5) |
C3—N1—C5 | 111.1 (4) | C8—C9—H9A | 124.7 |
C3—N1—C1 | 110.1 (4) | N5—C9—H9A | 124.7 |
C5—N1—C1 | 111.1 (4) | N6—C10—H10A | 109.5 |
C3—N1—Cu1 | 109.5 (3) | N6—C10—H10B | 109.5 |
C5—N1—Cu1 | 106.9 (3) | H10A—C10—H10B | 109.5 |
C1—N1—Cu1 | 108.0 (3) | N6—C10—H10C | 109.5 |
C2—N2—Cu1 | 106.1 (3) | H10A—C10—H10C | 109.5 |
C2—N2—H2C | 110.5 | H10B—C10—H10C | 109.5 |
Cu1—N2—H2C | 110.5 | N7—C11—C12 | 111.0 (4) |
C2—N2—H2D | 110.5 | N7—C11—H11A | 109.4 |
Cu1—N2—H2D | 110.5 | C12—C11—H11A | 109.4 |
H2C—N2—H2D | 108.7 | N7—C11—H11B | 109.4 |
C4—N3—Cu1 | 108.0 (3) | C12—C11—H11B | 109.4 |
C4—N3—H3C | 110.1 | H11A—C11—H11B | 108.0 |
Cu1—N3—H3C | 110.1 | N8—C12—C11 | 108.6 (4) |
C4—N3—H3D | 110.1 | N8—C12—H12A | 110.0 |
Cu1—N3—H3D | 110.1 | C11—C12—H12A | 110.0 |
H3C—N3—H3D | 108.4 | N8—C12—H12B | 110.0 |
C6—N4—Cu1 | 109.1 (3) | C11—C12—H12B | 110.0 |
C6—N4—H4C | 109.9 | H12A—C12—H12B | 108.4 |
Cu1—N4—H4C | 109.9 | N7—C13—C14 | 109.8 (4) |
C6—N4—H4D | 109.9 | N7—C13—H13A | 109.7 |
Cu1—N4—H4D | 109.9 | C14—C13—H13A | 109.7 |
H4C—N4—H4D | 108.3 | N7—C13—H13B | 109.7 |
C7—N5—C9 | 104.2 (5) | C14—C13—H13B | 109.7 |
C7—N5—Cu1 | 126.5 (4) | H13A—C13—H13B | 108.2 |
C9—N5—Cu1 | 129.2 (4) | N9—C14—C13 | 108.9 (4) |
C7—N6—C8 | 106.7 (5) | N9—C14—H14A | 109.9 |
C7—N6—C10 | 127.5 (5) | C13—C14—H14A | 109.9 |
C8—N6—C10 | 125.8 (5) | N9—C14—H14B | 109.9 |
C15—N7—C11 | 111.0 (4) | C13—C14—H14B | 109.9 |
C15—N7—C13 | 111.0 (4) | H14A—C14—H14B | 108.3 |
C11—N7—C13 | 111.3 (4) | N7—C15—C16 | 110.1 (4) |
C15—N7—Cu2 | 109.1 (3) | N7—C15—H15A | 109.6 |
C11—N7—Cu2 | 107.4 (3) | C16—C15—H15A | 109.6 |
C13—N7—Cu2 | 106.8 (3) | N7—C15—H15B | 109.6 |
C12—N8—Cu2 | 107.7 (3) | C16—C15—H15B | 109.6 |
C12—N8—H8B | 110.2 | H15A—C15—H15B | 108.1 |
Cu2—N8—H8B | 110.2 | N10—C16—C15 | 106.7 (4) |
C12—N8—H8C | 110.2 | N10—C16—H16A | 110.4 |
Cu2—N8—H8C | 110.2 | C15—C16—H16A | 110.4 |
H8B—N8—H8C | 108.5 | N10—C16—H16B | 110.4 |
C14—N9—Cu2 | 110.6 (3) | C15—C16—H16B | 110.4 |
C14—N9—H9B | 109.5 | H16A—C16—H16B | 108.6 |
Cu2—N9—H9B | 109.5 | N11—C17—N12 | 111.3 (5) |
C14—N9—H9C | 109.5 | N11—C17—H17A | 124.4 |
Cu2—N9—H9C | 109.5 | N12—C17—H17A | 124.4 |
H9B—N9—H9C | 108.1 | C19—C18—N12 | 106.3 (5) |
C16—N10—Cu2 | 106.2 (3) | C19—C18—H18A | 126.8 |
C16—N10—H10D | 110.5 | N12—C18—H18A | 126.8 |
Cu2—N10—H10D | 110.5 | C18—C19—N11 | 109.6 (5) |
C16—N10—H10E | 110.5 | C18—C19—H19A | 125.2 |
Cu2—N10—H10E | 110.5 | N11—C19—H19A | 125.2 |
H10D—N10—H10E | 108.7 | N12—C20—H20A | 109.5 |
C17—N11—C19 | 105.6 (5) | N12—C20—H20B | 109.5 |
C17—N11—Cu2 | 127.6 (4) | H20A—C20—H20B | 109.5 |
C19—N11—Cu2 | 126.8 (4) | N12—C20—H20C | 109.5 |
C17—N12—C18 | 107.2 (5) | H20A—C20—H20C | 109.5 |
C17—N12—C20 | 125.7 (5) | H20B—C20—H20C | 109.5 |
N4—Cu1—N1—C3 | −139.4 (3) | N9—Cu2—N11—C19 | −33.7 (5) |
N3—Cu1—N1—C3 | −9.6 (3) | N10—Cu2—N11—C19 | −167.7 (5) |
N2—Cu1—N1—C3 | 107.7 (3) | N8—Cu2—N11—C19 | 81.2 (5) |
N4—Cu1—N1—C5 | −18.9 (3) | C3—N1—C1—C2 | −80.2 (5) |
N3—Cu1—N1—C5 | 110.8 (3) | C5—N1—C1—C2 | 156.3 (4) |
N2—Cu1—N1—C5 | −131.8 (3) | Cu1—N1—C1—C2 | 39.4 (4) |
N4—Cu1—N1—C1 | 100.7 (3) | Cu1—N2—C2—C1 | 41.4 (5) |
N3—Cu1—N1—C1 | −129.6 (3) | N1—C1—C2—N2 | −55.2 (5) |
N2—Cu1—N1—C1 | −12.2 (3) | C5—N1—C3—C4 | −82.6 (5) |
N5—Cu1—N2—C2 | 162.8 (3) | C1—N1—C3—C4 | 153.9 (4) |
N1—Cu1—N2—C2 | −16.4 (3) | Cu1—N1—C3—C4 | 35.3 (4) |
N4—Cu1—N2—C2 | −98.5 (3) | Cu1—N3—C4—C3 | 42.4 (5) |
N3—Cu1—N2—C2 | 63.3 (4) | N1—C3—C4—N3 | −52.0 (5) |
N5—Cu1—N3—C4 | 159.9 (4) | C3—N1—C5—C6 | 161.9 (4) |
N1—Cu1—N3—C4 | −18.5 (4) | C1—N1—C5—C6 | −75.2 (5) |
N4—Cu1—N3—C4 | 59.8 (4) | Cu1—N1—C5—C6 | 42.4 (5) |
N2—Cu1—N3—C4 | −98.5 (4) | Cu1—N4—C6—C5 | 32.6 (5) |
N5—Cu1—N4—C6 | 174.4 (4) | N1—C5—C6—N4 | −50.5 (6) |
N1—Cu1—N4—C6 | −8.0 (4) | C9—N5—C7—N6 | 0.1 (7) |
N3—Cu1—N4—C6 | −85.6 (4) | Cu1—N5—C7—N6 | −176.0 (4) |
N2—Cu1—N4—C6 | 73.4 (4) | C8—N6—C7—N5 | −0.7 (7) |
N4—Cu1—N5—C7 | 165.4 (5) | C10—N6—C7—N5 | 177.8 (6) |
N3—Cu1—N5—C7 | 36.0 (5) | C7—N6—C8—C9 | 1.0 (8) |
N2—Cu1—N5—C7 | −81.4 (5) | C10—N6—C8—C9 | −177.6 (7) |
N4—Cu1—N5—C9 | −9.8 (6) | N6—C8—C9—N5 | −1.0 (9) |
N3—Cu1—N5—C9 | −139.2 (6) | C7—N5—C9—C8 | 0.6 (8) |
N2—Cu1—N5—C9 | 103.4 (6) | Cu1—N5—C9—C8 | 176.6 (5) |
N9—Cu2—N7—C15 | −140.4 (3) | C15—N7—C11—C12 | −78.6 (5) |
N10—Cu2—N7—C15 | −6.2 (3) | C13—N7—C11—C12 | 157.2 (4) |
N8—Cu2—N7—C15 | 104.8 (3) | Cu2—N7—C11—C12 | 40.6 (4) |
N9—Cu2—N7—C11 | 99.1 (3) | Cu2—N8—C12—C11 | 35.7 (5) |
N10—Cu2—N7—C11 | −126.7 (3) | N7—C11—C12—N8 | −52.1 (5) |
N8—Cu2—N7—C11 | −15.7 (3) | C15—N7—C13—C14 | 162.0 (4) |
N9—Cu2—N7—C13 | −20.3 (3) | C11—N7—C13—C14 | −73.8 (5) |
N10—Cu2—N7—C13 | 113.9 (3) | Cu2—N7—C13—C14 | 43.1 (5) |
N8—Cu2—N7—C13 | −135.1 (3) | Cu2—N9—C14—C13 | 30.7 (5) |
N11—Cu2—N8—C12 | 168.8 (3) | N7—C13—C14—N9 | −49.4 (6) |
N7—Cu2—N8—C12 | −11.4 (3) | C11—N7—C15—C16 | 152.2 (4) |
N9—Cu2—N8—C12 | −91.9 (3) | C13—N7—C15—C16 | −83.5 (5) |
N10—Cu2—N8—C12 | 69.8 (3) | Cu2—N7—C15—C16 | 34.0 (5) |
N11—Cu2—N9—C14 | 175.3 (4) | Cu2—N10—C16—C15 | 45.6 (5) |
N7—Cu2—N9—C14 | −5.8 (4) | N7—C15—C16—N10 | −53.7 (6) |
N10—Cu2—N9—C14 | −81.3 (4) | C19—N11—C17—N12 | 1.9 (7) |
N8—Cu2—N9—C14 | 75.0 (4) | Cu2—N11—C17—N12 | 178.6 (3) |
N11—Cu2—N10—C16 | 156.5 (4) | C18—N12—C17—N11 | −1.7 (7) |
N7—Cu2—N10—C16 | −22.3 (4) | C20—N12—C17—N11 | 179.6 (5) |
N9—Cu2—N10—C16 | 53.3 (4) | C17—N12—C18—C19 | 0.8 (7) |
N8—Cu2—N10—C16 | −103.8 (3) | C20—N12—C18—C19 | 179.5 (6) |
N9—Cu2—N11—C17 | 150.2 (5) | N12—C18—C19—N11 | 0.4 (8) |
N10—Cu2—N11—C17 | 16.3 (5) | C17—N11—C19—C18 | −1.4 (8) |
N8—Cu2—N11—C17 | −94.9 (5) | Cu2—N11—C19—C18 | −178.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2C···O11i | 0.90 | 2.28 | 3.086 (6) | 150 |
N2—H2D···O13ii | 0.90 | 2.26 | 3.110 (6) | 157 |
N3—H3C···O6iii | 0.90 | 2.56 | 3.260 (7) | 136 |
N3—H3D···O9iv | 0.90 | 2.40 | 3.151 (7) | 141 |
N4—H4C···O10iv | 0.90 | 2.22 | 3.072 (6) | 157 |
N4—H4D···O11i | 0.90 | 2.56 | 3.193 (7) | 128 |
N8—H8B···O7v | 0.90 | 2.33 | 3.094 (6) | 143 |
N8—H8C···O3 | 0.90 | 2.44 | 3.267 (5) | 154 |
N8—H8C···O4 | 0.90 | 2.47 | 3.218 (6) | 141 |
N9—H9B···O8vi | 0.90 | 2.23 | 3.050 (6) | 152 |
N9—H9C···O16 | 0.90 | 2.50 | 3.100 (6) | 125 |
N9—H9C···O7v | 0.90 | 2.43 | 3.086 (7) | 130 |
N10—H10D···O12 | 0.90 | 2.53 | 3.340 (8) | 150 |
N10—H10E···O2vii | 0.90 | 2.28 | 3.070 (6) | 146 |
C3—H3A···O6iii | 0.97 | 2.35 | 3.173 (6) | 142 |
C3—H3B···O3 | 0.97 | 2.58 | 3.547 (6) | 172 |
C6—H6B···O1i | 0.97 | 2.50 | 3.237 (6) | 132 |
C8—H8A···O13viii | 0.96 | 2.56 | 3.360 (8) | 143 |
C12—H12A···O12 | 0.97 | 2.53 | 3.426 (8) | 153 |
C15—H15B···O14vi | 0.97 | 2.54 | 3.511 (6) | 177 |
C17—H17A···O2vii | 0.93 | 2.56 | 3.318 (7) | 139 |
C18—H18A···O3ix | 0.93 | 2.52 | 3.377 (7) | 153 |
C20—H20B···O2ix | 0.96 | 2.60 | 3.385 (7) | 140 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) x+1/2, −y+1/2, z−1/2; (iv) −x+3/2, y−1/2, −z+1/2; (v) −x+1/2, y−1/2, −z+1/2; (vi) −x+1/2, y+1/2, −z+1/2; (vii) x, y+1, z; (viii) x+1, y, z; (ix) −x+1, −y, −z. |