Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229621006082/cu3173sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229621006082/cu3173Isup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229621006082/cu3173sup3.pdf | |
Microsoft Excel (XLSX) file https://doi.org/10.1107/S2053229621006082/cu3173sup4.xlsx |
CCDC reference: 2089247
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: APEX2 (Bruker, 2005); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: PLATON (Spek, 2020), enCIFer (Allen et al., 2004) and publCIF (Westrip, 2010).
[Cu(C9H10NO4)2]·H2O | F(000) = 980 |
Mr = 473.93 | Dx = 1.650 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 9886 reflections |
a = 9.5938 (3) Å | θ = 2.9–30.1° |
b = 20.1903 (6) Å | µ = 1.20 mm−1 |
c = 10.1806 (3) Å | T = 120 K |
β = 104.663 (1)° | Prism fragment, purple |
V = 1907.77 (10) Å3 | 0.42 × 0.12 × 0.10 mm |
Z = 4 |
Bruker–Nonius Kappa APEXII diffractometer | 10252 reflections with I > 2.0σ(I) |
Graphite monochromator | Rint = 0.043 |
φ & ω scans | θmax = 30.1°, θmin = 2.0° |
Absorption correction: numerical Apex2 (Bruker, 2005) | h = −13→13 |
Tmin = 0.87, Tmax = 0.89 | k = −28→28 |
42508 measured reflections | l = −14→14 |
11278 independent reflections |
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.029 | Method = Modified Sheldrick
w = 1/[σ2(F2) + ( 0.03P)2 + 0.42P]
, where P = (max(Fo2,0) + 2Fc2)/3 |
wR(F2) = 0.068 | (Δ/σ)max = 0.007 |
S = 0.99 | Δρmax = 0.37 e Å−3 |
11278 reflections | Δρmin = −0.52 e Å−3 |
622 parameters | Absolute structure: (Parsons et al., 2013), 5226 Friedel Pairs |
1 restraint | Absolute structure parameter: −0.004 (4) |
Primary atom site location: structure-invariant direct methods |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.51301 (2) | 0.50311 (3) | 0.114284 (19) | 0.0142 | |
Cu101 | 0.49775 (2) | 0.50175 (3) | 0.608835 (19) | 0.0138 | |
O1 | 0.66157 (14) | 0.52981 (8) | 0.02848 (13) | 0.0188 | |
O2 | 0.86792 (14) | 0.58473 (7) | 0.06738 (13) | 0.0175 | |
O3 | 0.83732 (16) | 0.54095 (7) | 0.80600 (14) | 0.0196 | |
O4 | 0.69969 (15) | 0.65695 (8) | 0.82795 (14) | 0.0177 | |
O5 | 0.37789 (14) | 0.48310 (7) | −0.05574 (13) | 0.0160 | |
O6 | 0.16353 (14) | 0.43846 (8) | −0.14624 (13) | 0.0183 | |
O7 | 0.22698 (18) | 0.46056 (8) | 0.61315 (14) | 0.0249 | |
O8 | 0.10034 (17) | 0.33893 (8) | 0.62028 (14) | 0.0245 | |
O19 | 0.88092 (17) | 0.26056 (9) | 0.64716 (17) | 0.0225 | |
O20 | 0.02002 (18) | 0.32281 (9) | 0.89437 (16) | 0.0237 | |
O101 | 0.55638 (15) | 0.43741 (7) | 0.49274 (13) | 0.0185 | |
O102 | 0.67228 (15) | 0.34191 (7) | 0.49476 (14) | 0.0195 | |
O103 | 0.25485 (15) | 0.27720 (7) | 1.06015 (14) | 0.0175 | |
O104 | 0.46310 (16) | 0.31998 (8) | 1.26613 (14) | 0.0182 | |
O105 | 0.44158 (14) | 0.56480 (7) | 0.46285 (12) | 0.0145 | |
O106 | 0.34839 (16) | 0.66543 (7) | 0.41691 (13) | 0.0192 | |
O107 | 0.41490 (15) | 0.63598 (8) | 1.17953 (14) | 0.0202 | |
O108 | 0.12458 (16) | 0.64519 (8) | 1.16640 (14) | 0.0193 | |
N1 | 0.64854 (18) | 0.53403 (9) | 0.28361 (16) | 0.0166 | |
N2 | 0.36401 (18) | 0.47070 (10) | 0.19890 (16) | 0.0165 | |
N101 | 0.5965 (2) | 0.44406 (9) | 0.75873 (17) | 0.0181 | |
N102 | 0.43555 (18) | 0.56932 (8) | 0.72093 (15) | 0.0128 | |
C1 | 0.76087 (19) | 0.56511 (10) | 0.10362 (18) | 0.0143 | |
C2 | 0.73929 (19) | 0.58521 (10) | 0.24212 (18) | 0.0137 | |
C3 | 0.8784 (2) | 0.59980 (11) | 0.35089 (18) | 0.0181 | |
C4 | 0.84232 (19) | 0.61801 (10) | 0.48259 (18) | 0.0158 | |
C5 | 0.86094 (19) | 0.57200 (10) | 0.58780 (19) | 0.0165 | |
C6 | 0.81582 (19) | 0.58652 (10) | 0.70415 (18) | 0.0142 | |
C7 | 0.74904 (19) | 0.64722 (10) | 0.71397 (18) | 0.0149 | |
C8 | 0.7333 (2) | 0.69388 (10) | 0.6109 (2) | 0.0186 | |
C9 | 0.7810 (2) | 0.67925 (10) | 0.49620 (19) | 0.0189 | |
C10 | 0.2598 (2) | 0.45565 (9) | −0.04659 (18) | 0.0139 | |
C11 | 0.24153 (18) | 0.44149 (9) | 0.09600 (17) | 0.0122 | |
C12 | 0.0957 (2) | 0.46224 (10) | 0.11855 (18) | 0.0165 | |
C13 | 0.07895 (19) | 0.43226 (10) | 0.24961 (18) | 0.0157 | |
C14 | 0.1444 (2) | 0.46214 (10) | 0.37456 (19) | 0.0162 | |
C15 | 0.1511 (2) | 0.43058 (10) | 0.49633 (19) | 0.0168 | |
C16 | 0.0864 (2) | 0.36862 (10) | 0.49675 (19) | 0.0178 | |
C17 | 0.0162 (2) | 0.33983 (11) | 0.3745 (2) | 0.0214 | |
C18 | 0.0143 (2) | 0.37065 (11) | 0.2517 (2) | 0.0205 | |
C101 | 0.6237 (2) | 0.38691 (9) | 0.55381 (18) | 0.0146 | |
C102 | 0.6393 (2) | 0.38103 (9) | 0.70681 (18) | 0.0146 | |
C103 | 0.5424 (2) | 0.32370 (10) | 0.73150 (19) | 0.0181 | |
C104 | 0.5295 (2) | 0.32037 (10) | 0.87663 (18) | 0.0157 | |
C105 | 0.3981 (2) | 0.30093 (9) | 0.90055 (19) | 0.0162 | |
C106 | 0.3807 (2) | 0.29868 (9) | 1.03136 (19) | 0.0148 | |
C107 | 0.4919 (2) | 0.31892 (9) | 1.14134 (18) | 0.0149 | |
C108 | 0.6236 (2) | 0.33747 (10) | 1.11872 (19) | 0.0167 | |
C109 | 0.6426 (2) | 0.33724 (10) | 0.98777 (19) | 0.0169 | |
C110 | 0.37911 (19) | 0.61731 (9) | 0.49305 (17) | 0.0134 | |
C111 | 0.33577 (19) | 0.61485 (9) | 0.62827 (17) | 0.0124 | |
C112 | 0.3276 (2) | 0.68284 (9) | 0.69264 (18) | 0.0138 | |
C113 | 0.27348 (19) | 0.67665 (9) | 0.81930 (17) | 0.0124 | |
C114 | 0.36810 (19) | 0.66323 (9) | 0.94590 (18) | 0.0130 | |
C115 | 0.3175 (2) | 0.65288 (9) | 1.06027 (17) | 0.0133 | |
C116 | 0.1703 (2) | 0.65700 (9) | 1.05084 (18) | 0.0150 | |
C117 | 0.0763 (2) | 0.67272 (10) | 0.9279 (2) | 0.0174 | |
C118 | 0.1273 (2) | 0.68117 (10) | 0.81228 (18) | 0.0158 | |
H11 | 0.704 (3) | 0.5037 (15) | 0.323 (2) | 0.023 (6)* | |
H12 | 0.607 (3) | 0.5513 (13) | 0.342 (3) | 0.026 (7)* | |
H21 | 0.396 (3) | 0.4438 (15) | 0.260 (3) | 0.031 (7)* | |
H22 | 0.330 (3) | 0.5007 (17) | 0.233 (3) | 0.033 (7)* | |
H23 | 0.6818 | 0.6235 | 0.2243 | 0.0148* | |
H31 | 0.836 (3) | 0.5575 (15) | 0.880 (3) | 0.036 (8)* | |
H32 | 0.9388 | 0.5606 | 0.3633 | 0.0212* | |
H33 | 0.9269 | 0.6358 | 0.3201 | 0.0210* | |
H41 | 0.713 (3) | 0.6919 (16) | 0.854 (3) | 0.037 (8)* | |
H51 | 0.9040 | 0.5314 | 0.5808 | 0.0199* | |
H71 | 0.209 (3) | 0.4477 (14) | 0.676 (3) | 0.028 (7)* | |
H81 | 0.044 (3) | 0.3063 (15) | 0.614 (3) | 0.032 (7)* | |
H82 | 0.6856 | 0.7330 | 0.6182 | 0.0214* | |
H91 | 0.7713 | 0.7109 | 0.4254 | 0.0233* | |
H111 | 0.2504 | 0.3937 | 0.1099 | 0.0152* | |
H121 | 0.0932 | 0.5107 | 0.1211 | 0.0192* | |
H122 | 0.0252 | 0.4472 | 0.0443 | 0.0191* | |
H141 | 0.1825 | 0.5045 | 0.3770 | 0.0207* | |
H171 | −0.0291 | 0.2981 | 0.3751 | 0.0262* | |
H181 | −0.0335 | 0.3508 | 0.1716 | 0.0247* | |
H191 | 0.849 (3) | 0.2285 (15) | 0.659 (3) | 0.024 (7)* | |
H192 | 0.819 (4) | 0.2775 (16) | 0.598 (3) | 0.037 (9)* | |
H201 | 0.063 (3) | 0.3605 (17) | 0.873 (3) | 0.045 (8)* | |
H202 | −0.022 (4) | 0.301 (2) | 0.839 (4) | 0.057 (11)* | |
H1011 | 0.549 (3) | 0.4378 (15) | 0.819 (3) | 0.037 (8)* | |
H1012 | 0.661 (3) | 0.4643 (14) | 0.799 (3) | 0.030 (8)* | |
H1021 | 0.400 (3) | 0.5513 (13) | 0.782 (3) | 0.023 (6)* | |
H1022 | 0.505 (3) | 0.5879 (12) | 0.765 (3) | 0.017 (6)* | |
H1023 | 0.7388 | 0.3716 | 0.7494 | 0.0170* | |
H1031 | 0.182 (4) | 0.2868 (15) | 0.998 (3) | 0.043 (9)* | |
H1032 | 0.5795 | 0.2817 | 0.7090 | 0.0222* | |
H1033 | 0.4475 | 0.3294 | 0.6722 | 0.0223* | |
H1041 | 0.529 (3) | 0.3310 (15) | 1.314 (3) | 0.033 (8)* | |
H1051 | 0.3217 | 0.2890 | 0.8278 | 0.0178* | |
H1071 | 0.392 (3) | 0.6428 (13) | 1.241 (3) | 0.023 (7)* | |
H1081 | 0.051 (3) | 0.6335 (14) | 1.145 (3) | 0.024 (7)* | |
H1082 | 0.6987 | 0.3516 | 1.1892 | 0.0189* | |
H1091 | 0.7357 | 0.3484 | 0.9729 | 0.0208* | |
H1111 | 0.2417 | 0.5951 | 0.6088 | 0.0143* | |
H1121 | 0.2631 | 0.7108 | 0.6265 | 0.0163* | |
H1122 | 0.4242 | 0.6998 | 0.7147 | 0.0166* | |
H1141 | 0.4650 | 0.6595 | 0.9540 | 0.0165* | |
H1171 | −0.0224 | 0.6758 | 0.9212 | 0.0209* | |
H1181 | 0.0648 | 0.6907 | 0.7284 | 0.0192* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.01493 (10) | 0.02034 (10) | 0.00822 (9) | −0.00505 (10) | 0.00459 (7) | −0.00047 (10) |
Cu101 | 0.02195 (10) | 0.01243 (9) | 0.00787 (8) | 0.00180 (10) | 0.00509 (7) | 0.00034 (10) |
O1 | 0.0179 (6) | 0.0296 (7) | 0.0102 (6) | −0.0077 (6) | 0.0059 (5) | −0.0033 (5) |
O2 | 0.0156 (6) | 0.0264 (7) | 0.0121 (6) | −0.0042 (5) | 0.0064 (5) | 0.0007 (5) |
O3 | 0.0287 (8) | 0.0190 (7) | 0.0124 (6) | 0.0002 (6) | 0.0079 (6) | 0.0000 (5) |
O4 | 0.0207 (7) | 0.0205 (7) | 0.0146 (6) | −0.0013 (5) | 0.0095 (5) | −0.0055 (5) |
O5 | 0.0175 (6) | 0.0220 (7) | 0.0090 (5) | −0.0055 (5) | 0.0045 (5) | 0.0005 (4) |
O6 | 0.0190 (6) | 0.0255 (7) | 0.0098 (6) | −0.0052 (5) | 0.0030 (5) | −0.0019 (5) |
O7 | 0.0364 (9) | 0.0301 (8) | 0.0093 (6) | −0.0182 (7) | 0.0074 (6) | −0.0039 (6) |
O8 | 0.0326 (8) | 0.0262 (8) | 0.0143 (6) | −0.0133 (7) | 0.0054 (6) | 0.0012 (6) |
O19 | 0.0187 (7) | 0.0180 (8) | 0.0289 (8) | −0.0044 (6) | 0.0028 (6) | 0.0031 (6) |
O20 | 0.0227 (8) | 0.0277 (8) | 0.0196 (7) | −0.0065 (7) | 0.0031 (6) | 0.0017 (6) |
O101 | 0.0300 (8) | 0.0154 (6) | 0.0108 (6) | 0.0045 (6) | 0.0067 (5) | 0.0011 (5) |
O102 | 0.0232 (7) | 0.0221 (7) | 0.0138 (6) | 0.0052 (5) | 0.0061 (5) | −0.0010 (5) |
O103 | 0.0162 (6) | 0.0200 (7) | 0.0170 (6) | −0.0014 (5) | 0.0053 (5) | 0.0039 (5) |
O104 | 0.0189 (7) | 0.0246 (7) | 0.0112 (6) | 0.0008 (6) | 0.0039 (5) | 0.0005 (5) |
O105 | 0.0209 (6) | 0.0153 (6) | 0.0087 (5) | 0.0036 (5) | 0.0061 (5) | 0.0007 (5) |
O106 | 0.0280 (7) | 0.0194 (7) | 0.0103 (6) | 0.0062 (6) | 0.0053 (5) | 0.0034 (5) |
O107 | 0.0180 (7) | 0.0357 (8) | 0.0085 (6) | 0.0064 (6) | 0.0065 (5) | 0.0041 (6) |
O108 | 0.0156 (7) | 0.0326 (8) | 0.0120 (6) | −0.0080 (6) | 0.0075 (5) | −0.0037 (6) |
N1 | 0.0181 (8) | 0.0230 (9) | 0.0104 (7) | −0.0036 (7) | 0.0068 (6) | −0.0010 (6) |
N2 | 0.0171 (8) | 0.0246 (9) | 0.0086 (7) | −0.0040 (7) | 0.0044 (6) | −0.0004 (6) |
N101 | 0.0285 (9) | 0.0144 (8) | 0.0109 (7) | 0.0003 (7) | 0.0041 (7) | −0.0009 (6) |
N102 | 0.0153 (7) | 0.0143 (7) | 0.0095 (6) | −0.0010 (6) | 0.0044 (6) | 0.0006 (6) |
C1 | 0.0159 (8) | 0.0174 (8) | 0.0097 (7) | 0.0006 (7) | 0.0038 (6) | 0.0021 (6) |
C2 | 0.0132 (8) | 0.0184 (8) | 0.0104 (7) | −0.0007 (6) | 0.0046 (6) | −0.0005 (6) |
C3 | 0.0140 (8) | 0.0293 (10) | 0.0118 (8) | −0.0027 (7) | 0.0047 (7) | −0.0037 (7) |
C4 | 0.0129 (8) | 0.025 (1) | 0.0098 (8) | −0.0031 (7) | 0.0035 (6) | −0.0043 (7) |
C5 | 0.0140 (8) | 0.0209 (9) | 0.0143 (8) | −0.0006 (7) | 0.0031 (7) | −0.0044 (7) |
C6 | 0.0123 (8) | 0.0192 (8) | 0.0111 (7) | −0.0042 (7) | 0.0027 (6) | −0.0016 (6) |
C7 | 0.0122 (8) | 0.0215 (9) | 0.0115 (8) | −0.0029 (7) | 0.0039 (6) | −0.0043 (7) |
C8 | 0.0184 (9) | 0.0190 (9) | 0.0182 (9) | 0.0002 (7) | 0.0044 (7) | −0.0018 (7) |
C9 | 0.0194 (9) | 0.0241 (10) | 0.0130 (8) | −0.0031 (8) | 0.0036 (7) | 0.0012 (7) |
C10 | 0.0181 (8) | 0.0143 (8) | 0.0107 (7) | −0.0009 (7) | 0.0063 (6) | −0.0009 (6) |
C11 | 0.0139 (8) | 0.0150 (8) | 0.0086 (7) | −0.0014 (6) | 0.0045 (6) | 0.0006 (6) |
C12 | 0.0146 (8) | 0.0234 (9) | 0.0124 (8) | 0.0015 (7) | 0.0052 (6) | 0.0010 (7) |
C13 | 0.0126 (8) | 0.0229 (9) | 0.0126 (8) | 0.0014 (7) | 0.0054 (6) | 0.0003 (7) |
C14 | 0.0168 (9) | 0.0168 (8) | 0.0173 (8) | −0.0019 (7) | 0.0084 (7) | −0.0012 (7) |
C15 | 0.0170 (8) | 0.0215 (9) | 0.0136 (8) | −0.0052 (7) | 0.0069 (7) | −0.0040 (7) |
C16 | 0.0182 (9) | 0.0230 (10) | 0.0131 (8) | −0.0046 (7) | 0.0053 (7) | −0.0001 (7) |
C17 | 0.0215 (10) | 0.0249 (10) | 0.0188 (9) | −0.0093 (8) | 0.0071 (8) | −0.0048 (8) |
C18 | 0.0188 (9) | 0.0274 (10) | 0.0147 (8) | −0.0067 (8) | 0.0031 (7) | −0.0062 (7) |
C101 | 0.0159 (8) | 0.0163 (8) | 0.0111 (7) | −0.0008 (6) | 0.0028 (7) | 0.0001 (6) |
C102 | 0.0180 (9) | 0.0151 (8) | 0.0109 (7) | 0.0013 (7) | 0.0038 (7) | 0.0000 (6) |
C103 | 0.0251 (10) | 0.0188 (9) | 0.0117 (8) | −0.0027 (7) | 0.0071 (7) | −0.0003 (7) |
C104 | 0.0215 (9) | 0.0146 (8) | 0.0120 (8) | 0.0012 (7) | 0.0062 (7) | 0.0003 (6) |
C105 | 0.0198 (9) | 0.0134 (8) | 0.0146 (8) | 0.0002 (7) | 0.0029 (7) | 0.0007 (6) |
C106 | 0.0171 (8) | 0.0121 (8) | 0.0159 (8) | 0.0011 (7) | 0.0056 (7) | 0.0028 (6) |
C107 | 0.0181 (9) | 0.0134 (8) | 0.0133 (8) | 0.0034 (7) | 0.0045 (7) | 0.0024 (6) |
C108 | 0.0180 (9) | 0.0190 (9) | 0.0129 (8) | 0.0013 (7) | 0.0036 (7) | 0.0015 (7) |
C109 | 0.0179 (9) | 0.0176 (9) | 0.0160 (8) | 0.0004 (7) | 0.0058 (7) | 0.0028 (7) |
C110 | 0.0151 (8) | 0.0163 (8) | 0.0086 (7) | −0.0010 (6) | 0.0028 (6) | 0.0002 (6) |
C111 | 0.0148 (8) | 0.0143 (8) | 0.0087 (7) | −0.0014 (6) | 0.0039 (6) | −0.0011 (6) |
C112 | 0.0179 (8) | 0.0144 (8) | 0.0100 (7) | 0.0014 (7) | 0.0053 (6) | −0.0004 (6) |
C113 | 0.0161 (8) | 0.0113 (8) | 0.0112 (7) | −0.0003 (6) | 0.0059 (6) | −0.0007 (6) |
C114 | 0.0127 (8) | 0.0152 (8) | 0.0119 (8) | 0.0000 (6) | 0.0047 (6) | 0.0001 (6) |
C115 | 0.0171 (8) | 0.0139 (8) | 0.0091 (7) | 0.0008 (6) | 0.0037 (6) | 0.0002 (6) |
C116 | 0.0185 (9) | 0.0163 (9) | 0.0126 (8) | −0.0031 (7) | 0.0082 (7) | −0.0024 (6) |
C117 | 0.0110 (8) | 0.0247 (10) | 0.0173 (9) | −0.0009 (7) | 0.0052 (7) | −0.0027 (7) |
C118 | 0.0148 (8) | 0.0208 (9) | 0.0105 (7) | −0.0010 (7) | 0.0010 (6) | 0.0003 (6) |
Cu1—O1 | 1.9276 (13) | C4—C5 | 1.395 (3) |
Cu1—O5 | 1.9245 (13) | C4—C9 | 1.391 (3) |
Cu1—N1 | 1.9792 (16) | C5—C6 | 1.391 (2) |
Cu1—N2 | 1.9589 (16) | C5—H51 | 0.929 |
Cu101—O101 | 1.9332 (13) | C6—C7 | 1.398 (3) |
Cu101—O105 | 1.9273 (13) | C7—C8 | 1.390 (3) |
Cu101—N101 | 1.9623 (17) | C8—C9 | 1.389 (3) |
Cu101—N102 | 1.9659 (16) | C8—H82 | 0.925 |
O1—C1 | 1.277 (2) | C9—H91 | 0.950 |
O2—C1 | 1.241 (2) | C10—C11 | 1.533 (2) |
O3—C6 | 1.362 (2) | C11—C12 | 1.532 (2) |
O3—H31 | 0.83 (3) | C11—H111 | 0.976 |
O4—C7 | 1.374 (2) | C12—C13 | 1.510 (2) |
O4—H41 | 0.76 (3) | C12—H121 | 0.979 |
O5—C10 | 1.285 (2) | C12—H122 | 0.929 |
O6—C10 | 1.236 (2) | C13—C14 | 1.404 (3) |
O7—C15 | 1.368 (2) | C13—C18 | 1.392 (3) |
O7—H71 | 0.75 (3) | C14—C15 | 1.381 (3) |
O8—C16 | 1.369 (2) | C14—H141 | 0.927 |
O8—H81 | 0.84 (3) | C15—C16 | 1.397 (3) |
O19—H191 | 0.74 (3) | C16—C17 | 1.385 (3) |
O19—H192 | 0.76 (3) | C17—C18 | 1.392 (3) |
O20—H201 | 0.92 (3) | C17—H171 | 0.949 |
O20—H202 | 0.75 (4) | C18—H181 | 0.920 |
O101—C101 | 1.281 (2) | C101—C102 | 1.531 (2) |
O102—C101 | 1.243 (2) | C102—C103 | 1.544 (3) |
O103—C106 | 1.382 (2) | C102—H1023 | 0.962 |
O103—H1031 | 0.84 (3) | C103—C104 | 1.515 (2) |
O104—C107 | 1.367 (2) | C103—H1032 | 0.969 |
O104—H1041 | 0.73 (3) | C103—H1033 | 0.964 |
O105—C110 | 1.293 (2) | C104—C105 | 1.399 (3) |
O106—C110 | 1.231 (2) | C104—C109 | 1.397 (3) |
O107—C115 | 1.375 (2) | C105—C106 | 1.384 (3) |
O107—H1071 | 0.73 (3) | C105—H1051 | 0.932 |
O108—C116 | 1.376 (2) | C106—C107 | 1.398 (3) |
O108—H1081 | 0.73 (3) | C107—C108 | 1.392 (3) |
N1—C2 | 1.480 (2) | C108—C109 | 1.391 (3) |
N1—H11 | 0.84 (3) | C108—H1082 | 0.924 |
N1—H12 | 0.86 (3) | C109—H1091 | 0.969 |
N2—C11 | 1.484 (2) | C110—C111 | 1.536 (2) |
N2—H21 | 0.82 (3) | C111—C112 | 1.532 (2) |
N2—H22 | 0.81 (3) | C111—H1111 | 0.960 |
N101—C102 | 1.476 (2) | C112—C113 | 1.512 (2) |
N101—H1011 | 0.87 (3) | C112—H1121 | 0.971 |
N101—H1012 | 0.77 (3) | C112—H1122 | 0.960 |
N102—C111 | 1.481 (2) | C113—C114 | 1.402 (2) |
N102—H1021 | 0.86 (3) | C113—C118 | 1.390 (3) |
N102—H1022 | 0.79 (3) | C114—C115 | 1.386 (2) |
C1—C2 | 1.531 (2) | C114—H1141 | 0.916 |
C2—C3 | 1.532 (2) | C115—C116 | 1.394 (3) |
C2—H23 | 0.941 | C116—C117 | 1.382 (3) |
C3—C4 | 1.513 (2) | C117—C118 | 1.394 (3) |
C3—H32 | 0.971 | C117—H1171 | 0.934 |
C3—H33 | 0.958 | C118—H1181 | 0.931 |
O1—Cu1—O5 | 93.33 (5) | C12—C11—H111 | 107.3 |
O1—Cu1—N1 | 84.74 (6) | C11—C12—C13 | 109.18 (15) |
O5—Cu1—N1 | 173.72 (7) | C11—C12—H121 | 107.9 |
O1—Cu1—N2 | 176.72 (8) | C13—C12—H121 | 111.6 |
O5—Cu1—N2 | 85.70 (6) | C11—C12—H122 | 107.1 |
N1—Cu1—N2 | 96.55 (7) | C13—C12—H122 | 111.6 |
O101—Cu101—O105 | 92.31 (5) | H121—C12—H122 | 109.3 |
O101—Cu101—N101 | 85.34 (6) | C12—C13—C14 | 120.32 (17) |
O105—Cu101—N101 | 167.81 (7) | C12—C13—C18 | 121.27 (17) |
O101—Cu101—N102 | 177.86 (6) | C14—C13—C18 | 117.94 (17) |
O105—Cu101—N102 | 85.56 (6) | C13—C14—C15 | 121.57 (17) |
N101—Cu101—N102 | 96.78 (7) | C13—C14—H141 | 120.2 |
Cu1—O1—C1 | 114.18 (11) | C15—C14—H141 | 118.2 |
C6—O3—H31 | 113 (2) | C14—C15—O7 | 118.03 (17) |
C7—O4—H41 | 112 (2) | C14—C15—C16 | 119.75 (17) |
Cu1—O5—C10 | 115.51 (11) | O7—C15—C16 | 122.17 (17) |
C15—O7—H71 | 114 (2) | C15—C16—O8 | 117.06 (17) |
C16—O8—H81 | 111.5 (19) | C15—C16—C17 | 119.25 (18) |
H191—O19—H192 | 103 (3) | O8—C16—C17 | 123.66 (18) |
H201—O20—H202 | 120 (3) | C16—C17—C18 | 120.81 (19) |
Cu101—O101—C101 | 115.29 (11) | C16—C17—H171 | 119.1 |
C106—O103—H1031 | 112 (2) | C18—C17—H171 | 120.1 |
C107—O104—H1041 | 106 (2) | C13—C18—C17 | 120.58 (18) |
Cu101—O105—C110 | 114.48 (11) | C13—C18—H181 | 120.0 |
C115—O107—H1071 | 116 (2) | C17—C18—H181 | 119.4 |
C116—O108—H1081 | 107 (2) | O101—C101—O102 | 123.49 (17) |
Cu1—N1—C2 | 106.02 (11) | O101—C101—C102 | 117.58 (16) |
Cu1—N1—H11 | 112.4 (18) | O102—C101—C102 | 118.89 (16) |
C2—N1—H11 | 107.2 (17) | C101—C102—N101 | 109.47 (15) |
Cu1—N1—H12 | 114.2 (17) | C101—C102—C103 | 108.41 (15) |
C2—N1—H12 | 108.6 (18) | N101—C102—C103 | 110.79 (16) |
H11—N1—H12 | 108 (2) | C101—C102—H1023 | 107.7 |
Cu1—N2—C11 | 110.96 (11) | N101—C102—H1023 | 110.1 |
Cu1—N2—H21 | 112.1 (19) | C103—C102—H1023 | 110.4 |
C11—N2—H21 | 110 (2) | C102—C103—C104 | 113.15 (15) |
Cu1—N2—H22 | 111 (2) | C102—C103—H1032 | 110.2 |
C11—N2—H22 | 105.8 (19) | C104—C103—H1032 | 108.5 |
H21—N2—H22 | 106 (3) | C102—C103—H1033 | 108.7 |
Cu101—N101—C102 | 110.89 (12) | C104—C103—H1033 | 108.6 |
Cu101—N101—H1011 | 113.6 (19) | H1032—C103—H1033 | 107.5 |
C102—N101—H1011 | 112 (2) | C103—C104—C105 | 118.81 (17) |
Cu101—N101—H1012 | 105 (2) | C103—C104—C109 | 122.70 (17) |
C102—N101—H1012 | 113 (2) | C105—C104—C109 | 118.48 (17) |
H1011—N101—H1012 | 102 (3) | C104—C105—C106 | 120.68 (17) |
Cu101—N102—C111 | 107.65 (11) | C104—C105—H1051 | 119.7 |
Cu101—N102—H1021 | 111.1 (17) | C106—C105—H1051 | 119.6 |
C111—N102—H1021 | 114.3 (17) | C105—C106—O103 | 122.62 (17) |
Cu101—N102—H1022 | 108.9 (17) | C105—C106—C107 | 120.48 (17) |
C111—N102—H1022 | 112.2 (17) | O103—C106—C107 | 116.89 (16) |
H1021—N102—H1022 | 103 (2) | C106—C107—O104 | 117.14 (16) |
O1—C1—O2 | 123.22 (16) | C106—C107—C108 | 119.14 (17) |
O1—C1—C2 | 116.44 (15) | O104—C107—C108 | 123.72 (17) |
O2—C1—C2 | 120.29 (16) | C107—C108—C109 | 120.20 (17) |
C1—C2—N1 | 107.71 (15) | C107—C108—H1082 | 121.1 |
C1—C2—C3 | 114.87 (15) | C109—C108—H1082 | 118.7 |
N1—C2—C3 | 113.32 (15) | C104—C109—C108 | 120.88 (17) |
C1—C2—H23 | 104.5 | C104—C109—H1091 | 119.2 |
N1—C2—H23 | 105.7 | C108—C109—H1091 | 119.9 |
C3—C2—H23 | 110.1 | O105—C110—O106 | 123.29 (16) |
C2—C3—C4 | 109.53 (15) | O105—C110—C111 | 115.70 (15) |
C2—C3—H32 | 108.6 | O106—C110—C111 | 120.90 (16) |
C4—C3—H32 | 110.2 | C110—C111—N102 | 108.23 (14) |
C2—C3—H33 | 108.4 | C110—C111—C112 | 114.16 (14) |
C4—C3—H33 | 110.1 | N102—C111—C112 | 112.24 (14) |
H32—C3—H33 | 109.8 | C110—C111—H1111 | 106.4 |
C3—C4—C5 | 120.35 (17) | N102—C111—H1111 | 107.2 |
C3—C4—C9 | 120.13 (17) | C112—C111—H1111 | 108.2 |
C5—C4—C9 | 119.38 (17) | C111—C112—C113 | 110.88 (14) |
C4—C5—C6 | 120.42 (18) | C111—C112—H1121 | 108.4 |
C4—C5—H51 | 120.2 | C113—C112—H1121 | 110.0 |
C6—C5—H51 | 119.4 | C111—C112—H1122 | 105.6 |
C5—C6—O3 | 119.07 (17) | C113—C112—H1122 | 110.4 |
C5—C6—C7 | 119.51 (17) | H1121—C112—H1122 | 111.3 |
O3—C6—C7 | 121.42 (16) | C112—C113—C114 | 121.17 (16) |
C6—C7—O4 | 116.62 (16) | C112—C113—C118 | 120.72 (16) |
C6—C7—C8 | 120.29 (17) | C114—C113—C118 | 118.05 (16) |
O4—C7—C8 | 123.08 (17) | C113—C114—C115 | 121.21 (16) |
C7—C8—C9 | 119.64 (18) | C113—C114—H1141 | 120.3 |
C7—C8—H82 | 118.7 | C115—C114—H1141 | 118.4 |
C9—C8—H82 | 121.6 | C114—C115—O107 | 118.34 (16) |
C4—C9—C8 | 120.67 (18) | C114—C115—C116 | 119.85 (16) |
C4—C9—H91 | 119.0 | O107—C115—C116 | 121.75 (16) |
C8—C9—H91 | 120.3 | C115—C116—O108 | 117.86 (16) |
O5—C10—O6 | 123.41 (16) | C115—C116—C117 | 119.56 (16) |
O5—C10—C11 | 117.61 (15) | O108—C116—C117 | 122.58 (17) |
O6—C10—C11 | 118.94 (16) | C116—C117—C118 | 120.35 (17) |
C10—C11—N2 | 109.54 (14) | C116—C117—H1171 | 119.9 |
C10—C11—C12 | 114.76 (15) | C118—C117—H1171 | 119.7 |
N2—C11—C12 | 112.04 (15) | C117—C118—C113 | 120.90 (17) |
C10—C11—H111 | 107.2 | C117—C118—H1181 | 121.2 |
N2—C11—H111 | 105.4 | C113—C118—H1181 | 117.9 |
O5—Cu1—O1—C1 | 161.25 (14) | O5—C10—C11—N2 | 6.5 (2) |
N1—Cu1—O1—C1 | −12.77 (14) | O5—C10—C11—C12 | 133.48 (18) |
O1—Cu1—O5—C10 | 173.19 (14) | O6—C10—C11—N2 | −175.80 (17) |
N2—Cu1—O5—C10 | −3.66 (14) | O6—C10—C11—C12 | −48.8 (2) |
O1—Cu1—N1—C2 | 26.68 (12) | N2—C11—C12—C13 | −66.8 (2) |
N2—Cu1—N1—C2 | −156.36 (13) | C10—C11—C12—C13 | 167.48 (15) |
O5—Cu1—N2—C11 | 7.06 (13) | C11—C12—C13—C14 | 80.9 (2) |
N1—Cu1—N2—C11 | −178.83 (13) | C11—C12—C13—C18 | −91.1 (2) |
O101—Cu101—O7—C15 | −31.75 (14) | C12—C13—C14—C15 | −169.27 (18) |
O105—Cu101—O7—C15 | 62.44 (14) | C18—C13—C14—C15 | 3.0 (3) |
N101—Cu101—O7—C15 | −118.04 (14) | C12—C13—C18—C17 | 171.66 (18) |
N102—Cu101—O7—C15 | 146.05 (14) | C14—C13—C18—C17 | −0.5 (3) |
O7—Cu101—O101—C101 | −91.05 (14) | C13—C14—C15—O7 | 174.69 (18) |
O105—Cu101—O101—C101 | 170.61 (14) | C13—C14—C15—C16 | −2.7 (3) |
N101—Cu101—O101—C101 | 2.60 (14) | O7—C15—C16—O8 | 0.8 (3) |
O7—Cu101—O105—C110 | 70.03 (13) | O7—C15—C16—C17 | −177.36 (19) |
O101—Cu101—O105—C110 | 173.76 (13) | C14—C15—C16—O8 | 178.10 (18) |
N102—Cu101—O105—C110 | −6.07 (13) | C14—C15—C16—C17 | −0.1 (3) |
O7—Cu101—N101—C102 | 94.08 (13) | O8—C16—C17—C18 | −175.54 (19) |
O101—Cu101—N101—C102 | −8.90 (13) | C15—C16—C17—C18 | 2.5 (3) |
N102—Cu101—N101—C102 | 171.38 (14) | C16—C17—C18—C13 | −2.2 (3) |
O7—Cu101—N102—C111 | −77.86 (12) | O101—C101—C102—N101 | −11.5 (2) |
O105—Cu101—N102—C111 | 20.99 (12) | O101—C101—C102—C103 | 109.38 (19) |
N101—Cu101—N102—C111 | −171.04 (12) | O102—C101—C102—N101 | 170.75 (17) |
Cu1—O1—C1—O2 | 177.24 (15) | O102—C101—C102—C103 | −68.3 (2) |
Cu1—O1—C1—C2 | −5.2 (2) | N101—C102—C103—C104 | −50.3 (2) |
Cu1—O5—C10—O6 | −178.41 (15) | C101—C102—C103—C104 | −170.41 (16) |
Cu1—O5—C10—C11 | −0.8 (2) | C102—C103—C104—C105 | 144.39 (18) |
Cu101—O7—C15—C14 | −49.3 (2) | C102—C103—C104—C109 | −34.3 (3) |
Cu101—O7—C15—C16 | 127.99 (17) | C103—C104—C105—C106 | −178.52 (18) |
Cu101—O101—C101—O102 | −177.94 (15) | C109—C104—C105—C106 | 0.2 (3) |
Cu101—O101—C101—C102 | 4.5 (2) | C103—C104—C109—C108 | 175.96 (19) |
Cu101—O105—C110—O106 | 172.90 (15) | C105—C104—C109—C108 | −2.7 (3) |
Cu101—O105—C110—C111 | −10.8 (2) | C104—C105—C106—O103 | −177.28 (17) |
Cu1—N1—C2—C1 | −34.17 (17) | C104—C105—C106—C107 | 3.2 (3) |
Cu1—N1—C2—C3 | −162.38 (13) | O103—C106—C107—O104 | −4.3 (3) |
Cu1—N2—C11—C10 | −8.74 (19) | O103—C106—C107—C108 | 176.44 (17) |
Cu1—N2—C11—C12 | −137.27 (13) | C105—C106—C107—O104 | 175.25 (17) |
Cu101—N101—C102—C101 | 12.65 (19) | C105—C106—C107—C108 | −4.0 (3) |
Cu101—N101—C102—C103 | −106.83 (15) | O104—C107—C108—C109 | −177.69 (18) |
Cu101—N102—C111—C110 | −30.06 (16) | C106—C107—C108—C109 | 1.5 (3) |
Cu101—N102—C111—C112 | −156.94 (12) | C107—C108—C109—C104 | 1.9 (3) |
O1—C1—C2—N1 | 27.4 (2) | O105—C110—C111—N102 | 27.8 (2) |
O1—C1—C2—C3 | 154.67 (18) | O105—C110—C111—C112 | 153.59 (16) |
O2—C1—C2—N1 | −154.97 (18) | O106—C110—C111—N102 | −155.76 (17) |
O2—C1—C2—C3 | −27.7 (3) | O106—C110—C111—C112 | −30.0 (2) |
N1—C2—C3—C4 | −54.8 (2) | N102—C111—C112—C113 | −60.7 (2) |
C1—C2—C3—C4 | −179.20 (17) | C110—C111—C112—C113 | 175.68 (15) |
C2—C3—C4—C5 | 102.6 (2) | C111—C112—C113—C114 | 86.0 (2) |
C2—C3—C4—C9 | −73.0 (2) | C111—C112—C113—C118 | −91.1 (2) |
C3—C4—C5—C6 | −174.21 (18) | C112—C113—C114—C115 | −175.36 (17) |
C9—C4—C5—C6 | 1.4 (3) | C118—C113—C114—C115 | 1.8 (3) |
C3—C4—C9—C8 | 173.12 (18) | C112—C113—C118—C117 | 177.28 (18) |
C5—C4—C9—C8 | −2.5 (3) | C114—C113—C118—C117 | 0.1 (3) |
C4—C5—C6—O3 | −179.08 (17) | C113—C114—C115—O107 | 176.11 (17) |
C4—C5—C6—C7 | 1.2 (3) | C113—C114—C115—C116 | −1.2 (3) |
O3—C6—C7—O4 | −3.3 (3) | O107—C115—C116—O108 | 1.6 (3) |
O3—C6—C7—C8 | 177.55 (18) | O107—C115—C116—C117 | −178.54 (18) |
C5—C6—C7—O4 | 176.39 (17) | C114—C115—C116—O108 | 178.85 (17) |
C5—C6—C7—C8 | −2.7 (3) | C114—C115—C116—C117 | −1.3 (3) |
O4—C7—C8—C9 | −177.41 (18) | O108—C116—C117—C118 | −176.97 (18) |
C6—C7—C8—C9 | 1.6 (3) | C115—C116—C117—C118 | 3.2 (3) |
C7—C8—C9—C4 | 1.0 (3) | C116—C117—C118—C113 | −2.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N101—H1011···O5i | 0.86 (3) | 2.49 (3) | 3.255 (2) | 148 (3) |
N101—H1012···O3 | 0.77 (3) | 2.28 (3) | 2.972 (2) | 150 (3) |
N102—H1021···O5i | 0.86 (3) | 2.20 (3) | 3.024 (2) | 159 (3) |
N102—H1022···O4 | 0.80 (3) | 2.29 (3) | 3.056 (2) | 162 (3) |
O103—H1031···O20 | 0.84 (3) | 1.80 (4) | 2.617 (2) | 166 (3) |
O104—H1041···O102i | 0.73 (3) | 2.01 (3) | 2.698 (2) | 157 (3) |
O107—H1071···O106i | 0.73 (3) | 1.99 (3) | 2.717 (2) | 174 (3) |
O107—H1071···O108 | 0.73 (3) | 2.49 (3) | 2.761 (2) | 105 (3) |
N1—H12···O105 | 0.87 (3) | 2.26 (3) | 3.081 (2) | 158 (3) |
O108—H1081···O2ii | 0.72 (3) | 1.99 (3) | 2.704 (2) | 167 (3) |
N2—H21···O101 | 0.82 (3) | 2.48 (3) | 3.164 (2) | 141 (3) |
N2—H21···O104iii | 0.82 (3) | 2.58 (3) | 3.210 (3) | 134 (3) |
O3—H31···O1i | 0.83 (3) | 2.58 (3) | 3.156 (2) | 127 (3) |
O3—H31···O2i | 0.83 (3) | 1.93 (3) | 2.7483 (19) | 168 (3) |
O3—H31···O4 | 0.83 (3) | 2.38 (3) | 2.725 (2) | 106 (2) |
O4—H41···O103iv | 0.75 (3) | 1.92 (3) | 2.670 (2) | 174 (3) |
O7—H71···O6i | 0.75 (3) | 1.98 (3) | 2.706 (2) | 165 (3) |
O7—H71···O8 | 0.75 (3) | 2.44 (3) | 2.749 (2) | 107 (2) |
O8—H81···O19v | 0.84 (3) | 1.92 (3) | 2.702 (2) | 154 (3) |
O19—H191···O106vi | 0.74 (3) | 2.25 (3) | 2.868 (2) | 142 (3) |
O19—H191···O108vii | 0.74 (3) | 2.41 (3) | 3.014 (2) | 140 (3) |
O19—H192···O102 | 0.76 (3) | 2.01 (3) | 2.746 (2) | 166 (3) |
O20—H201···O6i | 0.92 (3) | 1.88 (3) | 2.794 (2) | 172 (3) |
O20—H202···O19v | 0.75 (4) | 2.10 (4) | 2.827 (2) | 163 (4) |
C2—H23···O107iii | 0.94 | 2.50 | 3.184 (2) | 130 |
C11—H111···O103iii | 0.98 | 2.41 | 3.343 (2) | 160 |
C12—H121···O2v | 0.98 | 2.57 | 3.254 (2) | 127 |
Symmetry codes: (i) x, y, z+1; (ii) x−1, y, z+1; (iii) x, y, z−1; (iv) −x+1, y+1/2, −z+2; (v) x−1, y, z; (vi) −x+1, y−1/2, −z+1; (vii) −x+1, y−1/2, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A | Label |
N101—H1011···O5i | 0.86 (3) | 2.49 (3) | 3.255 (2) | 148 (3) | a |
N101—H1012···O3 | 0.77 (3) | 2.28 (3) | 2.972 (2) | 150 (3) | b |
N102—H1021···O5i | 0.86 (3) | 2.20 (3) | 3.024 (2) | 159 (3) | c |
N102—H1022···O4 | 0.80 (3) | 2.29 (3) | 3.056 (2) | 162 (3) | d |
O104—H1041···O102i | 0.73 (3) | 2.01 (3) | 2.698 (2) | 157 (3) | e |
O107—H1071···O106i | 0.73 (3) | 1.99 (3) | 2.717 (2) | 174 (3) | f |
N1—H12···O105 | 0.87 (3) | 2.26 (3) | 3.081 (2) | 158 (3) | g |
N2—H21···O101 | 0.82 (3) | 2.48 (3) | 3.164 (2) | 141 (3) | h |
N2—H21···O104ii | 0.82 (3) | 2.58 (3) | 3.210 (3) | 134 (3) | i |
O3—H31···O1i | 0.83 (3) | 2.58 (3) | 3.156 (2) | 127 (3) | j |
O3—H31···O2i | 0.83 (3) | 1.93 (3) | 2.7483 (19) | 168 (3) | k |
O7—H71···O6i | 0.75 (3) | 1.98 (3) | 2.706 (2) | 165 (3) | l |
O19—H191···O106iii | 0.74 (3) | 2.25 (3) | 2.868 (2) | 142 (3) | |
O19—H192···O102 | 0.76 (3) | 2.01 (3) | 2.746 (2) | 166 (3) |
Symmetry codes: (i) x, y, z+1; (ii) x, y, z-1; (iii) 1-x, -1/2+y, 1-z |