Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229622011147/ef3037sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229622011147/ef3037Isup2.hkl |
CCDC reference: 2220960
Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: olex2.solve (Bourhis et al., 2015) and SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
[Cu(C12H6NO3)(C12H8N2)(H2O)]NO3·CH4O | Z = 2 |
Mr = 567.99 | F(000) = 582 |
Triclinic, P1 | Dx = 1.649 Mg m−3 |
a = 10.4795 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.1326 (4) Å | Cell parameters from 6405 reflections |
c = 12.1768 (7) Å | θ = 2.2–27.8° |
α = 101.393 (3)° | µ = 1.02 mm−1 |
β = 105.793 (3)° | T = 296 K |
γ = 115.958 (2)° | Block, clear dark blue |
V = 1143.78 (9) Å3 | 0.23 × 0.21 × 0.2 mm |
Bruker SMART X2S benchtop diffractometer | 5312 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
φ and ω scans | θmax = 31.9°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2010) | h = −15→15 |
Tmin = 0.618, Tmax = 0.746 | k = −16→16 |
27013 measured reflections | l = −18→17 |
7598 independent reflections |
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.042 | w = 1/[σ2(Fo2) + (0.0591P)2 + 0.0324P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.116 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.51 e Å−3 |
7598 reflections | Δρmin = −0.52 e Å−3 |
424 parameters | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0026 (8) |
Primary atom site location: iterative |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Single crystal data of complex (1) was collected on a Bruker SMART X2S benchtop crystallographic system. Intensity measurements were performed using monochromated (doubly curved silicon crystal) Mo Kα radiation (λ = 0.71073 Å) from a sealed microfocus tube. Generator settings were 50 kV, 1 mA. APEX2 software was used for preliminary determination of the unit cell. Determination of integrated intensities and unit cell refinement were performed using SAINT (Bruker, 2010). Data were corrected for absorption effects with SADABS (Bruker, 2010) using the multiscan technique. The structure was resolved on Olex2.0 (Dolomanov et al., 2009) package using ShelxT (Sheldrick, 2015a) and refined by full-matrix least squares based on F2, using ShelexL (Sheldrick, 2015b). Crystal data, data collection and structurerefinementdetails for complex (1) were summarized in Table1. All non-H atoms were refined anisotropically. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.64849 (3) | 0.47282 (2) | 0.09574 (2) | 0.03270 (9) | |
O2 | 0.60399 (16) | 0.59194 (13) | 0.20029 (13) | 0.0378 (3) | |
O1 | 0.82505 (16) | 0.65190 (13) | 0.12556 (13) | 0.0378 (3) | |
O3 | 1.05760 (17) | 0.92025 (15) | 0.20820 (14) | 0.0444 (3) | |
N3 | 0.83009 (18) | 0.75864 (15) | 0.20769 (14) | 0.0300 (3) | |
O4 | 0.7782 (2) | 0.4286 (2) | 0.25361 (19) | 0.0527 (4) | |
N1 | 0.67338 (18) | 0.35070 (16) | −0.02946 (14) | 0.0313 (3) | |
N2 | 0.44867 (18) | 0.29220 (16) | 0.04833 (14) | 0.0314 (3) | |
N4 | 1.1322 (2) | 0.4470 (2) | 0.26569 (18) | 0.0502 (5) | |
O6 | 1.2572 (2) | 0.4545 (2) | 0.2942 (2) | 0.0767 (6) | |
C13 | 0.7114 (2) | 0.72106 (19) | 0.24422 (16) | 0.0296 (4) | |
C11 | 0.4391 (2) | 0.17856 (18) | −0.02764 (15) | 0.0292 (4) | |
O7 | 1.1117 (3) | 0.5264 (2) | 0.33672 (19) | 0.0781 (6) | |
C12 | 0.5604 (2) | 0.21025 (18) | −0.06963 (16) | 0.0295 (4) | |
C24 | 0.8370 (2) | 0.97461 (19) | 0.37522 (16) | 0.0301 (4) | |
C14 | 0.7135 (2) | 0.83134 (19) | 0.33304 (16) | 0.0302 (4) | |
C4 | 0.5598 (2) | 0.1002 (2) | −0.14860 (16) | 0.0335 (4) | |
C22 | 0.9561 (2) | 1.01076 (19) | 0.33264 (16) | 0.0311 (4) | |
O5 | 1.0225 (3) | 0.3588 (2) | 0.16730 (19) | 0.0938 (8) | |
C23 | 0.9582 (2) | 0.89902 (19) | 0.24617 (17) | 0.0310 (4) | |
C7 | 0.3184 (2) | 0.03686 (19) | −0.06388 (17) | 0.0342 (4) | |
C10 | 0.3371 (2) | 0.2677 (2) | 0.08843 (18) | 0.0378 (4) | |
C18 | 0.8392 (2) | 1.0827 (2) | 0.46117 (17) | 0.0370 (4) | |
C1 | 0.7878 (2) | 0.3845 (2) | −0.06660 (19) | 0.0394 (4) | |
C15 | 0.5978 (3) | 0.7963 (2) | 0.37510 (19) | 0.0380 (4) | |
C3 | 0.6844 (3) | 0.1400 (2) | −0.18313 (19) | 0.0419 (5) | |
C21 | 1.0734 (3) | 1.1519 (2) | 0.3729 (2) | 0.0409 (5) | |
C19 | 0.9624 (3) | 1.2259 (2) | 0.5010 (2) | 0.0465 (5) | |
C5 | 0.4337 (3) | −0.0446 (2) | −0.18556 (19) | 0.0413 (5) | |
C6 | 0.3202 (3) | −0.0743 (2) | −0.14541 (19) | 0.0406 (5) | |
C8 | 0.2061 (2) | 0.0145 (2) | −0.0164 (2) | 0.0423 (5) | |
C9 | 0.2157 (3) | 0.1295 (2) | 0.0591 (2) | 0.0450 (5) | |
C17 | 0.7203 (3) | 1.0430 (2) | 0.5032 (2) | 0.0443 (5) | |
C2 | 0.7980 (3) | 0.2812 (2) | −0.1430 (2) | 0.0446 (5) | |
C16 | 0.6031 (3) | 0.9044 (3) | 0.4617 (2) | 0.0456 (5) | |
C20 | 1.0754 (3) | 1.2593 (2) | 0.4568 (2) | 0.0488 (6) | |
O8 | 0.6589 (3) | 0.3415 (2) | 0.42340 (19) | 0.0636 (5) | |
C25 | 0.5354 (4) | 0.3651 (4) | 0.4039 (3) | 0.0671 (7) | |
H9 | 0.146 (3) | 0.119 (2) | 0.094 (2) | 0.039 (6)* | |
H1 | 0.863 (2) | 0.483 (2) | −0.0347 (18) | 0.035 (5)* | |
H16 | 0.535 (3) | 0.881 (2) | 0.489 (2) | 0.035 (6)* | |
H21 | 1.147 (3) | 1.171 (2) | 0.3417 (19) | 0.035 (6)* | |
H3 | 0.691 (3) | 0.076 (3) | −0.229 (2) | 0.052 (7)* | |
H2 | 0.885 (3) | 0.309 (2) | −0.165 (2) | 0.051 (7)* | |
H10 | 0.347 (3) | 0.345 (2) | 0.141 (2) | 0.041 (6)* | |
H17 | 0.713 (3) | 1.106 (3) | 0.558 (2) | 0.054 (7)* | |
H8 | 0.131 (3) | −0.073 (3) | −0.035 (3) | 0.069 (8)* | |
H15 | 0.513 (3) | 0.705 (3) | 0.346 (2) | 0.048 (7)* | |
H25A | 0.554 (4) | 0.439 (4) | 0.366 (3) | 0.097 (11)* | |
H6 | 0.242 (3) | −0.168 (3) | −0.163 (2) | 0.053 (7)* | |
H20 | 1.147 (4) | 1.358 (3) | 0.480 (3) | 0.081 (9)* | |
H5 | 0.437 (3) | −0.117 (3) | −0.240 (2) | 0.059 (7)* | |
H19 | 0.959 (3) | 1.284 (3) | 0.556 (2) | 0.061 (8)* | |
H25B | 0.436 (4) | 0.283 (4) | 0.345 (3) | 0.098 (11)* | |
H25C | 0.513 (4) | 0.385 (4) | 0.475 (3) | 0.095 (11)* | |
H8A | 0.712 (3) | 0.372 (3) | 0.492 (3) | 0.068 (10)* | |
H4A | 0.769 (3) | 0.410 (3) | 0.308 (2) | 0.041 (7)* | |
H4B | 0.845 (3) | 0.443 (3) | 0.257 (3) | 0.042 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.03265 (14) | 0.02420 (12) | 0.03814 (14) | 0.01289 (9) | 0.01809 (10) | 0.00498 (9) |
O2 | 0.0349 (7) | 0.0276 (6) | 0.0519 (8) | 0.0143 (6) | 0.0258 (6) | 0.0097 (6) |
O1 | 0.0407 (8) | 0.0268 (6) | 0.0485 (8) | 0.0169 (6) | 0.0281 (6) | 0.0063 (5) |
O3 | 0.0376 (8) | 0.0369 (7) | 0.0583 (9) | 0.0159 (6) | 0.0296 (7) | 0.0112 (6) |
N3 | 0.0321 (8) | 0.0254 (7) | 0.0349 (8) | 0.0154 (6) | 0.0184 (6) | 0.0080 (6) |
O4 | 0.0438 (11) | 0.0670 (12) | 0.0522 (11) | 0.0299 (9) | 0.0220 (9) | 0.0250 (9) |
N1 | 0.0318 (8) | 0.0275 (7) | 0.0338 (8) | 0.0146 (6) | 0.0161 (6) | 0.0081 (6) |
N2 | 0.0285 (7) | 0.0313 (7) | 0.0306 (7) | 0.0136 (6) | 0.0129 (6) | 0.0076 (6) |
N4 | 0.0464 (11) | 0.0515 (11) | 0.0468 (11) | 0.0189 (9) | 0.0219 (9) | 0.0189 (9) |
O6 | 0.0591 (12) | 0.0926 (15) | 0.0833 (14) | 0.0443 (12) | 0.0350 (11) | 0.0218 (11) |
C13 | 0.0312 (9) | 0.0288 (8) | 0.0318 (8) | 0.0175 (7) | 0.0148 (7) | 0.0097 (7) |
C11 | 0.0272 (8) | 0.0276 (8) | 0.0273 (8) | 0.0123 (7) | 0.0085 (7) | 0.0077 (6) |
O7 | 0.0967 (16) | 0.0973 (16) | 0.0668 (12) | 0.0713 (14) | 0.0359 (11) | 0.0263 (11) |
C12 | 0.0318 (9) | 0.0272 (8) | 0.0280 (8) | 0.0158 (7) | 0.0108 (7) | 0.0079 (6) |
C24 | 0.0347 (9) | 0.0286 (8) | 0.0289 (8) | 0.0197 (7) | 0.0111 (7) | 0.0088 (7) |
C14 | 0.0323 (9) | 0.0311 (8) | 0.0321 (9) | 0.0196 (7) | 0.0152 (7) | 0.0106 (7) |
C4 | 0.0382 (10) | 0.0322 (9) | 0.0291 (8) | 0.0217 (8) | 0.0100 (7) | 0.0066 (7) |
C22 | 0.0325 (9) | 0.0276 (8) | 0.0314 (9) | 0.0160 (7) | 0.0114 (7) | 0.0085 (7) |
O5 | 0.0658 (13) | 0.0812 (14) | 0.0640 (12) | −0.0015 (11) | 0.0078 (11) | 0.0156 (11) |
C23 | 0.0310 (9) | 0.0279 (8) | 0.0343 (9) | 0.0154 (7) | 0.0139 (7) | 0.0109 (7) |
C7 | 0.0283 (9) | 0.0296 (9) | 0.0351 (9) | 0.0119 (7) | 0.0066 (7) | 0.0101 (7) |
C10 | 0.0306 (9) | 0.0427 (11) | 0.0354 (10) | 0.0169 (8) | 0.0150 (8) | 0.0081 (8) |
C18 | 0.0447 (11) | 0.0374 (10) | 0.0325 (9) | 0.0269 (9) | 0.0141 (8) | 0.0081 (8) |
C1 | 0.0377 (11) | 0.0360 (10) | 0.0418 (10) | 0.0162 (9) | 0.0209 (9) | 0.0098 (8) |
C15 | 0.0373 (10) | 0.0410 (11) | 0.0417 (10) | 0.0235 (9) | 0.0203 (9) | 0.0129 (9) |
C3 | 0.0494 (12) | 0.0440 (11) | 0.0363 (10) | 0.0305 (10) | 0.0185 (9) | 0.0060 (9) |
C21 | 0.0404 (11) | 0.0311 (9) | 0.0452 (11) | 0.0153 (8) | 0.0168 (9) | 0.0111 (8) |
C19 | 0.0574 (14) | 0.0317 (10) | 0.0435 (11) | 0.0255 (10) | 0.0155 (10) | 0.0021 (9) |
C5 | 0.0438 (11) | 0.0289 (9) | 0.0404 (10) | 0.0197 (9) | 0.0086 (9) | 0.0023 (8) |
C6 | 0.0370 (10) | 0.0248 (9) | 0.0430 (11) | 0.0122 (8) | 0.0053 (9) | 0.0052 (8) |
C8 | 0.0280 (10) | 0.0381 (11) | 0.0476 (12) | 0.0095 (8) | 0.0110 (9) | 0.0155 (9) |
C9 | 0.0313 (10) | 0.0529 (13) | 0.0473 (12) | 0.0170 (9) | 0.0202 (9) | 0.0177 (10) |
C17 | 0.0554 (13) | 0.0465 (12) | 0.0395 (10) | 0.0352 (11) | 0.0220 (10) | 0.0075 (9) |
C2 | 0.0435 (12) | 0.0507 (12) | 0.0464 (12) | 0.0257 (10) | 0.0274 (10) | 0.0153 (10) |
C16 | 0.0484 (13) | 0.0562 (13) | 0.0467 (12) | 0.0337 (11) | 0.0295 (10) | 0.0165 (10) |
C20 | 0.0524 (14) | 0.0298 (10) | 0.0500 (12) | 0.0162 (10) | 0.0159 (10) | 0.0069 (9) |
O8 | 0.0681 (13) | 0.0665 (12) | 0.0513 (11) | 0.0357 (10) | 0.0237 (10) | 0.0115 (9) |
C25 | 0.0637 (19) | 0.080 (2) | 0.0540 (16) | 0.0337 (17) | 0.0247 (14) | 0.0257 (15) |
Cu1—O2 | 1.9480 (13) | C7—C8 | 1.397 (3) |
Cu1—O1 | 1.9102 (14) | C10—C9 | 1.391 (3) |
Cu1—O4 | 2.307 (2) | C10—H10 | 0.91 (2) |
Cu1—N1 | 1.9870 (15) | C18—C19 | 1.412 (3) |
Cu1—N2 | 1.9897 (15) | C18—C17 | 1.401 (3) |
O2—C13 | 1.254 (2) | C1—C2 | 1.392 (3) |
O1—N3 | 1.3645 (18) | C1—H1 | 0.94 (2) |
O3—C23 | 1.202 (2) | C15—C16 | 1.404 (3) |
N3—C13 | 1.356 (2) | C15—H15 | 0.92 (2) |
N3—C23 | 1.413 (2) | C3—C2 | 1.367 (3) |
O4—H4A | 0.75 (3) | C3—H3 | 0.85 (2) |
O4—H4B | 0.63 (3) | C21—C20 | 1.399 (3) |
N1—C12 | 1.359 (2) | C21—H21 | 0.92 (2) |
N1—C1 | 1.324 (3) | C19—C20 | 1.368 (4) |
N2—C11 | 1.358 (2) | C19—H19 | 0.85 (3) |
N2—C10 | 1.328 (3) | C5—C6 | 1.341 (3) |
N4—O6 | 1.220 (3) | C5—H5 | 0.96 (3) |
N4—O7 | 1.242 (3) | C6—H6 | 0.94 (3) |
N4—O5 | 1.232 (3) | C8—C9 | 1.367 (3) |
C13—C14 | 1.455 (2) | C8—H8 | 0.87 (3) |
C11—C12 | 1.426 (3) | C9—H9 | 0.91 (2) |
C11—C7 | 1.399 (2) | C17—C16 | 1.356 (3) |
C12—C4 | 1.397 (2) | C17—H17 | 0.92 (3) |
C24—C14 | 1.411 (3) | C2—H2 | 0.96 (3) |
C24—C22 | 1.408 (3) | C16—H16 | 0.83 (2) |
C24—C18 | 1.417 (2) | C20—H20 | 0.94 (3) |
C14—C15 | 1.374 (3) | O8—C25 | 1.399 (4) |
C4—C3 | 1.394 (3) | O8—H8A | 0.77 (3) |
C4—C5 | 1.439 (3) | C25—H25A | 0.99 (4) |
C22—C23 | 1.475 (2) | C25—H25B | 0.97 (4) |
C22—C21 | 1.377 (3) | C25—H25C | 0.97 (4) |
C7—C6 | 1.436 (3) | ||
O2—Cu1—O4 | 94.28 (7) | C8—C7—C6 | 125.03 (17) |
O2—Cu1—N1 | 172.42 (6) | N2—C10—C9 | 122.01 (19) |
O2—Cu1—N2 | 94.60 (6) | N2—C10—H10 | 116.8 (14) |
O1—Cu1—O2 | 84.06 (5) | C9—C10—H10 | 121.1 (14) |
O1—Cu1—O4 | 94.95 (7) | C19—C18—C24 | 118.1 (2) |
O1—Cu1—N1 | 97.09 (6) | C17—C18—C24 | 118.80 (19) |
O1—Cu1—N2 | 172.46 (6) | C17—C18—C19 | 123.07 (18) |
N1—Cu1—O4 | 93.08 (7) | N1—C1—C2 | 122.31 (19) |
N1—Cu1—N2 | 83.28 (6) | N1—C1—H1 | 114.7 (13) |
N2—Cu1—O4 | 92.55 (7) | C2—C1—H1 | 123.0 (13) |
C13—O2—Cu1 | 111.09 (12) | C14—C15—C16 | 119.5 (2) |
N3—O1—Cu1 | 108.65 (10) | C14—C15—H15 | 122.9 (15) |
O1—N3—C23 | 116.88 (14) | C16—C15—H15 | 117.5 (16) |
C13—N3—O1 | 117.31 (14) | C4—C3—H3 | 120.0 (17) |
C13—N3—C23 | 125.81 (14) | C2—C3—C4 | 120.54 (18) |
Cu1—O4—H4A | 138 (2) | C2—C3—H3 | 119.4 (17) |
Cu1—O4—H4B | 113 (3) | C22—C21—C20 | 120.3 (2) |
H4A—O4—H4B | 109 (3) | C22—C21—H21 | 117.0 (13) |
C12—N1—Cu1 | 111.23 (12) | C20—C21—H21 | 122.7 (14) |
C1—N1—Cu1 | 129.78 (13) | C18—C19—H19 | 112.9 (19) |
C1—N1—C12 | 118.58 (16) | C20—C19—C18 | 120.86 (19) |
C11—N2—Cu1 | 111.38 (12) | C20—C19—H19 | 126.1 (19) |
C10—N2—Cu1 | 129.86 (13) | C4—C5—H5 | 115.3 (16) |
C10—N2—C11 | 118.40 (16) | C6—C5—C4 | 121.54 (18) |
O6—N4—O7 | 120.5 (2) | C6—C5—H5 | 123.1 (16) |
O6—N4—O5 | 121.1 (2) | C7—C6—H6 | 115.5 (16) |
O5—N4—O7 | 118.4 (2) | C5—C6—C7 | 121.63 (18) |
O2—C13—N3 | 118.53 (15) | C5—C6—H6 | 122.7 (16) |
O2—C13—C14 | 122.44 (17) | C7—C8—H8 | 119.9 (19) |
N3—C13—C14 | 119.03 (16) | C9—C8—C7 | 119.58 (19) |
N2—C11—C12 | 116.43 (15) | C9—C8—H8 | 120.5 (19) |
N2—C11—C7 | 122.90 (17) | C10—C9—H9 | 117.7 (14) |
C7—C11—C12 | 120.67 (16) | C8—C9—C10 | 119.9 (2) |
N1—C12—C11 | 116.76 (15) | C8—C9—H9 | 122.4 (14) |
N1—C12—C4 | 122.81 (17) | C18—C17—H17 | 124.5 (17) |
C4—C12—C11 | 120.43 (16) | C16—C17—C18 | 121.25 (19) |
C14—C24—C18 | 118.88 (18) | C16—C17—H17 | 114.3 (17) |
C22—C24—C14 | 120.95 (16) | C1—C2—H2 | 120.1 (14) |
C22—C24—C18 | 120.16 (17) | C3—C2—C1 | 119.0 (2) |
C24—C14—C13 | 118.60 (17) | C3—C2—H2 | 121.0 (14) |
C15—C14—C13 | 120.57 (17) | C15—C16—H16 | 118.4 (15) |
C15—C14—C24 | 120.83 (17) | C17—C16—C15 | 120.7 (2) |
C12—C4—C5 | 117.93 (18) | C17—C16—H16 | 120.8 (15) |
C3—C4—C12 | 116.77 (17) | C21—C20—H20 | 123 (2) |
C3—C4—C5 | 125.29 (17) | C19—C20—C21 | 120.7 (2) |
C24—C22—C23 | 120.86 (16) | C19—C20—H20 | 115.9 (19) |
C21—C22—C24 | 119.87 (17) | C25—O8—H8A | 111 (2) |
C21—C22—C23 | 119.26 (18) | O8—C25—H25A | 108 (2) |
O3—C23—N3 | 120.30 (16) | O8—C25—H25B | 114 (2) |
O3—C23—C22 | 125.03 (17) | O8—C25—H25C | 115 (2) |
N3—C23—C22 | 114.67 (16) | H25A—C25—H25B | 104 (3) |
C11—C7—C6 | 117.80 (19) | H25A—C25—H25C | 114 (3) |
C8—C7—C11 | 117.16 (18) | H25B—C25—H25C | 101 (3) |
Cu1—O2—C13—N3 | 4.6 (2) | C24—C22—C23—N3 | 2.6 (2) |
Cu1—O2—C13—C14 | −175.06 (13) | C24—C22—C21—C20 | 0.6 (3) |
Cu1—O1—N3—C13 | −3.82 (18) | C24—C18—C19—C20 | 0.7 (3) |
Cu1—O1—N3—C23 | 176.80 (12) | C24—C18—C17—C16 | −1.0 (3) |
Cu1—N1—C12—C11 | 6.80 (19) | C14—C24—C22—C23 | −2.3 (3) |
Cu1—N1—C12—C4 | −173.48 (14) | C14—C24—C22—C21 | 178.44 (17) |
Cu1—N1—C1—C2 | 170.53 (15) | C14—C24—C18—C19 | −179.05 (17) |
Cu1—N2—C11—C12 | −6.89 (19) | C14—C24—C18—C17 | 1.3 (3) |
Cu1—N2—C11—C7 | 172.88 (13) | C14—C15—C16—C17 | 0.7 (3) |
Cu1—N2—C10—C9 | −169.80 (15) | C4—C3—C2—C1 | 0.3 (3) |
O2—C13—C14—C24 | −178.36 (16) | C4—C5—C6—C7 | 0.2 (3) |
O2—C13—C14—C15 | 1.8 (3) | C22—C24—C14—C13 | 0.0 (3) |
O1—N3—C13—O2 | −0.6 (2) | C22—C24—C14—C15 | 179.76 (17) |
O1—N3—C13—C14 | 179.13 (14) | C22—C24—C18—C19 | 0.6 (3) |
O1—N3—C23—O3 | −1.0 (3) | C22—C24—C18—C17 | −179.06 (17) |
O1—N3—C23—C22 | 178.62 (14) | C22—C21—C20—C19 | 0.7 (3) |
N3—C13—C14—C24 | 1.9 (2) | C23—N3—C13—O2 | 178.74 (16) |
N3—C13—C14—C15 | −177.86 (17) | C23—N3—C13—C14 | −1.6 (3) |
N1—C12—C4—C3 | 1.6 (3) | C23—C22—C21—C20 | −178.73 (18) |
N1—C12—C4—C5 | −179.70 (16) | C7—C11—C12—N1 | −179.71 (15) |
N1—C1—C2—C3 | 1.3 (3) | C7—C11—C12—C4 | 0.6 (3) |
N2—C11—C12—N1 | 0.1 (2) | C7—C8—C9—C10 | −0.2 (3) |
N2—C11—C12—C4 | −179.67 (15) | C10—N2—C11—C12 | 179.21 (16) |
N2—C11—C7—C6 | 179.49 (17) | C10—N2—C11—C7 | −1.0 (3) |
N2—C11—C7—C8 | −1.3 (3) | C18—C24—C14—C13 | 179.60 (16) |
N2—C10—C9—C8 | −2.2 (3) | C18—C24—C14—C15 | −0.6 (3) |
C13—N3—C23—O3 | 179.71 (18) | C18—C24—C22—C23 | 178.07 (16) |
C13—N3—C23—C22 | −0.7 (3) | C18—C24—C22—C21 | −1.2 (3) |
C13—C14—C15—C16 | 179.38 (17) | C18—C19—C20—C21 | −1.3 (3) |
C11—N2—C10—C9 | 2.8 (3) | C18—C17—C16—C15 | 0.0 (3) |
C11—C12—C4—C3 | −178.64 (17) | C1—N1—C12—C11 | −179.86 (17) |
C11—C12—C4—C5 | 0.0 (3) | C1—N1—C12—C4 | −0.1 (3) |
C11—C7—C6—C5 | 0.4 (3) | C3—C4—C5—C6 | 178.1 (2) |
C11—C7—C8—C9 | 1.8 (3) | C21—C22—C23—O3 | 1.5 (3) |
C12—N1—C1—C2 | −1.4 (3) | C21—C22—C23—N3 | −178.10 (17) |
C12—C11—C7—C6 | −0.7 (2) | C19—C18—C17—C16 | 179.4 (2) |
C12—C11—C7—C8 | 178.49 (17) | C5—C4—C3—C2 | 179.77 (19) |
C12—C4—C3—C2 | −1.7 (3) | C6—C7—C8—C9 | −179.00 (19) |
C12—C4—C5—C6 | −0.4 (3) | C8—C7—C6—C5 | −178.8 (2) |
C24—C14—C15—C16 | −0.4 (3) | C17—C18—C19—C20 | −179.7 (2) |
C24—C22—C23—O3 | −177.80 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
O8—H8A···O7i | 0.77 (3) | 2.05 (3) | 2.804 (3) | 168 (3) |
O4—H4A···O8 | 0.75 (3) | 2.10 (3) | 2.813 (3) | 159 (3) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
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