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A fluorophore-labelled copper(II) complex, aquabis(dimethylformamide-κO)(perchlorato-κO)[2-(quinolin-2-yl)-1,3-oxazolo[4,5-f][1,10]phenanthroline]copper(II) perchlorate monohydrate, [Cu(ClO4)(C22H12N4O)(C3H7NO)2(H2O)]ClO4·H2O, has been synthesized and characterized. A cyclic hydrogen-bonded water–perchlorate anionic cluster, i.e. [(ClO4)2(H2O)2]2−, has been identified within the structure. Each cyclic anionic cluster unit is interconnected by hydrogen bonding to the cation. The cations join into an infinite hydrogen-bonded chain running in the [010] direction. Furthermore, interaction of the complex with calf-thymus DNA (CT-DNA) and cellular localization within the cells was explored. Spectroscopic studies indicate that the compound has a good affinity for DNA and stains the nucleus of the cells.
Supporting information
CCDC reference: 1562837
Data collection: SAINT (Bruker, 2010); cell refinement: SMART (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
Aquabis(dimethylformamide-
κO)(perchlorato-
κO)[2-(quinolin-2-yl)-1,3-oxazolo[4,5-
f][1,10]phenanthroline]copper(II) perchlorate monohydrate
top
Crystal data top
[Cu(ClO4)(C22H12N4O)(C3H7NO)2(H2O)]ClO4·H2O | F(000) = 3256 |
Mr = 793.02 | Dx = 1.612 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54178 Å |
a = 48.675 (3) Å | Cell parameters from 4790 reflections |
b = 8.3750 (5) Å | θ = 1.9–64.5° |
c = 16.3155 (9) Å | µ = 3.12 mm−1 |
β = 100.716 (2)° | T = 173 K |
V = 6535.1 (6) Å3 | Rectangle, green |
Z = 8 | 0.28 × 0.22 × 0.17 mm |
Data collection top
Bruker X8 Proteum diffractometer | 4790 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.071 |
Absorption correction: multi-scan (SADABS; Bruker, 2010) | θmax = 64.5°, θmin = 5.4° |
Tmin = 0.482, Tmax = 0.505 | h = −56→54 |
29422 measured reflections | k = −9→9 |
5417 independent reflections | l = −15→19 |
Refinement top
Refinement on F2 | 157 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.132 | w = 1/[σ2(Fo2) + (0.0731P)2 + 16.1488P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.002 |
5417 reflections | Δρmax = 0.77 e Å−3 |
504 parameters | Δρmin = −0.48 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cu1 | 0.63808 (2) | 0.76800 (5) | 0.33515 (3) | 0.01822 (15) | |
O2 | 0.67770 (4) | 0.8210 (3) | 0.37130 (13) | 0.0231 (5) | |
O1 | 0.64467 (4) | 0.6953 (3) | 0.22641 (13) | 0.0232 (5) | |
O3 | 0.54145 (4) | 1.1271 (2) | 0.48962 (12) | 0.0212 (4) | |
O4 | 0.65005 (5) | 0.5336 (3) | 0.39334 (14) | 0.0283 (5) | |
H4A | 0.668680 | 0.514138 | 0.399543 | 0.042* | |
H4B | 0.641311 | 0.452483 | 0.362216 | 0.042* | |
N2 | 0.59662 (5) | 0.7598 (3) | 0.29512 (15) | 0.0172 (5) | |
N1 | 0.62665 (5) | 0.8758 (3) | 0.43273 (14) | 0.0187 (5) | |
N4 | 0.51555 (5) | 1.0462 (3) | 0.36830 (15) | 0.0176 (5) | |
N7 | 0.71619 (5) | 0.9632 (3) | 0.36123 (16) | 0.0231 (6) | |
N5 | 0.49830 (5) | 1.2951 (3) | 0.53244 (15) | 0.0189 (5) | |
O5 | 0.70583 (5) | 0.4386 (3) | 0.44686 (19) | 0.0468 (7) | |
H5A | 0.718900 | 0.438323 | 0.418626 | 0.070* | |
H5B | 0.706890 | 0.347375 | 0.470057 | 0.070* | |
N6 | 0.66992 (5) | 0.5341 (3) | 0.15751 (17) | 0.0284 (6) | |
C5 | 0.58248 (5) | 0.8501 (3) | 0.34240 (17) | 0.0164 (6) | |
C6 | 0.59897 (6) | 0.9109 (3) | 0.41920 (18) | 0.0171 (6) | |
C4 | 0.55404 (5) | 0.8880 (3) | 0.31771 (17) | 0.0171 (6) | |
C1 | 0.58274 (6) | 0.7023 (3) | 0.22309 (18) | 0.0195 (6) | |
H1 | 0.592133 | 0.636716 | 0.191453 | 0.023* | |
C26 | 0.68925 (6) | 0.9459 (4) | 0.35209 (19) | 0.0236 (7) | |
H26 | 0.677914 | 1.030785 | 0.330107 | 0.028* | |
C3 | 0.54021 (6) | 0.8312 (3) | 0.23980 (18) | 0.0196 (6) | |
H3 | 0.521589 | 0.857181 | 0.219960 | 0.024* | |
C11 | 0.55818 (6) | 1.0365 (3) | 0.44858 (18) | 0.0183 (6) | |
C23 | 0.66611 (6) | 0.6122 (4) | 0.22322 (19) | 0.0234 (7) | |
H23 | 0.679992 | 0.606736 | 0.270749 | 0.028* | |
C22 | 0.47685 (6) | 1.3819 (3) | 0.55422 (19) | 0.0209 (6) | |
C7 | 0.58712 (6) | 1.0027 (3) | 0.47580 (18) | 0.0186 (6) | |
C13 | 0.51640 (6) | 1.1273 (3) | 0.43692 (19) | 0.0208 (6) | |
C12 | 0.54243 (6) | 0.9866 (3) | 0.37484 (18) | 0.0184 (6) | |
C2 | 0.55461 (6) | 0.7368 (4) | 0.19342 (19) | 0.0212 (6) | |
H2 | 0.545639 | 0.695999 | 0.142404 | 0.025* | |
C8 | 0.60458 (6) | 1.0527 (4) | 0.54982 (19) | 0.0246 (7) | |
H8 | 0.597389 | 1.111196 | 0.589469 | 0.030* | |
C15 | 0.46711 (6) | 1.2196 (4) | 0.4050 (2) | 0.0227 (6) | |
H15 | 0.464676 | 1.164073 | 0.354847 | 0.027* | |
C10 | 0.64288 (6) | 0.9274 (4) | 0.50227 (19) | 0.0228 (6) | |
H10 | 0.661922 | 0.905087 | 0.511060 | 0.027* | |
C17 | 0.44993 (6) | 1.3887 (4) | 0.5025 (2) | 0.0242 (7) | |
C14 | 0.49310 (6) | 1.2182 (3) | 0.46072 (18) | 0.0181 (6) | |
C9 | 0.63232 (6) | 1.0138 (4) | 0.5625 (2) | 0.0263 (7) | |
H9 | 0.644151 | 1.045097 | 0.611341 | 0.032* | |
C16 | 0.44565 (6) | 1.3050 (4) | 0.4270 (2) | 0.0269 (7) | |
H16 | 0.428264 | 1.307446 | 0.391828 | 0.032* | |
C21 | 0.48177 (7) | 1.4658 (4) | 0.6303 (2) | 0.0278 (7) | |
H21 | 0.499320 | 1.461098 | 0.664476 | 0.033* | |
C18 | 0.42873 (7) | 1.4798 (4) | 0.5304 (2) | 0.0339 (8) | |
H18 | 0.410916 | 1.484971 | 0.497807 | 0.041* | |
C20 | 0.46102 (8) | 1.5540 (4) | 0.6545 (2) | 0.0364 (9) | |
H20 | 0.464707 | 1.610582 | 0.704394 | 0.044* | |
C19 | 0.43436 (8) | 1.5600 (4) | 0.6050 (3) | 0.0396 (9) | |
H19 | 0.420330 | 1.618773 | 0.622661 | 0.048* | |
C27 | 0.72853 (8) | 1.1103 (4) | 0.3384 (2) | 0.0389 (8) | |
H27A | 0.713995 | 1.185541 | 0.317883 | 0.058* | |
H27B | 0.739200 | 1.088833 | 0.295681 | 0.058* | |
H27C | 0.740586 | 1.153987 | 0.386435 | 0.058* | |
C24 | 0.64950 (9) | 0.5388 (6) | 0.0826 (3) | 0.0556 (12) | |
H24A | 0.632332 | 0.581308 | 0.094368 | 0.083* | |
H24B | 0.646343 | 0.432703 | 0.060585 | 0.083* | |
H24C | 0.656075 | 0.605475 | 0.042465 | 0.083* | |
C28 | 0.73515 (7) | 0.8364 (5) | 0.3937 (3) | 0.0517 (11) | |
H28A | 0.725217 | 0.755903 | 0.418378 | 0.078* | |
H28B | 0.749954 | 0.878560 | 0.435268 | 0.078* | |
H28C | 0.742904 | 0.790148 | 0.349225 | 0.078* | |
C25 | 0.69518 (9) | 0.4426 (5) | 0.1565 (3) | 0.0512 (11) | |
H25A | 0.707412 | 0.451478 | 0.209748 | 0.077* | |
H25B | 0.704433 | 0.483256 | 0.113808 | 0.077* | |
H25C | 0.690400 | 0.332488 | 0.145403 | 0.077* | |
Cl3 | 0.61575 (2) | 1.19401 (9) | 0.26661 (5) | 0.0271 (2) | |
O32 | 0.62515 (6) | 1.2378 (3) | 0.35322 (16) | 0.0436 (6) | |
O31 | 0.62935 (5) | 1.0488 (3) | 0.25143 (15) | 0.0358 (6) | |
O33 | 0.62201 (5) | 1.3185 (3) | 0.21300 (17) | 0.0414 (6) | |
O34 | 0.58625 (5) | 1.1691 (4) | 0.2537 (2) | 0.0533 (8) | |
Cl2 | 0.72028 (14) | 0.0671 (7) | 0.6164 (4) | 0.0330 (12) | 0.6667 |
O6 | 0.72004 (11) | 0.1404 (8) | 0.5356 (3) | 0.0508 (14) | 0.6667 |
O7 | 0.74955 (14) | 0.0373 (12) | 0.6530 (4) | 0.0347 (14) | 0.6667 |
O8 | 0.70409 (11) | −0.0720 (6) | 0.6185 (4) | 0.0594 (13) | 0.6667 |
O9 | 0.71221 (14) | 0.1840 (7) | 0.6718 (4) | 0.0653 (18) | 0.6667 |
Cl1 | 0.7185 (2) | 0.0605 (13) | 0.6059 (8) | 0.0297 (19) | 0.3333 |
O10 | 0.7077 (3) | 0.1569 (17) | 0.5390 (9) | 0.075 (3) | 0.3333 |
O11 | 0.7465 (3) | 0.040 (3) | 0.6321 (12) | 0.061 (4) | 0.3333 |
O13 | 0.71045 (14) | −0.0957 (9) | 0.5766 (6) | 0.0345 (16) | 0.3333 |
O12 | 0.7028 (2) | 0.1098 (15) | 0.6623 (7) | 0.062 (3) | 0.3333 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0134 (2) | 0.0240 (3) | 0.0190 (3) | 0.00191 (15) | 0.00771 (17) | −0.00228 (17) |
O2 | 0.0155 (10) | 0.0281 (11) | 0.0273 (11) | 0.0012 (8) | 0.0081 (8) | 0.0001 (9) |
O1 | 0.0179 (10) | 0.0317 (11) | 0.0217 (11) | 0.0055 (8) | 0.0081 (8) | −0.0015 (9) |
O3 | 0.0188 (10) | 0.0232 (11) | 0.0244 (11) | 0.0035 (8) | 0.0116 (8) | −0.0004 (9) |
O4 | 0.0319 (12) | 0.0250 (11) | 0.0287 (12) | 0.0029 (9) | 0.0075 (9) | 0.0020 (9) |
N2 | 0.0173 (12) | 0.0187 (12) | 0.0178 (13) | 0.0007 (9) | 0.0092 (10) | 0.0011 (10) |
N1 | 0.0174 (12) | 0.0224 (12) | 0.0177 (13) | −0.0008 (9) | 0.0070 (10) | 0.0009 (10) |
N4 | 0.0168 (12) | 0.0162 (12) | 0.0230 (13) | 0.0009 (9) | 0.0125 (10) | 0.0019 (10) |
N7 | 0.0224 (13) | 0.0245 (13) | 0.0244 (14) | −0.0028 (10) | 0.0091 (10) | −0.0018 (11) |
N5 | 0.0196 (12) | 0.0185 (12) | 0.0212 (13) | 0.0001 (9) | 0.0111 (10) | 0.0032 (10) |
O5 | 0.0396 (15) | 0.0463 (16) | 0.0588 (18) | 0.0157 (12) | 0.0204 (13) | 0.0135 (13) |
N6 | 0.0282 (14) | 0.0332 (15) | 0.0278 (15) | 0.0035 (11) | 0.0152 (12) | −0.0062 (12) |
C5 | 0.0171 (13) | 0.0164 (14) | 0.0177 (14) | −0.0015 (11) | 0.0086 (11) | 0.0019 (11) |
C6 | 0.0164 (13) | 0.0182 (14) | 0.0188 (15) | −0.0014 (11) | 0.0086 (11) | 0.0016 (12) |
C4 | 0.0168 (13) | 0.0167 (14) | 0.0206 (15) | −0.0028 (11) | 0.0110 (11) | 0.0036 (11) |
C1 | 0.0210 (14) | 0.0215 (15) | 0.0185 (15) | −0.0017 (11) | 0.0103 (12) | −0.0013 (12) |
C26 | 0.0235 (16) | 0.0230 (16) | 0.0244 (17) | 0.0019 (12) | 0.0046 (12) | −0.0025 (13) |
C3 | 0.0154 (13) | 0.0228 (15) | 0.0227 (16) | −0.0017 (11) | 0.0086 (11) | 0.0047 (12) |
C11 | 0.0195 (14) | 0.0162 (14) | 0.0231 (16) | 0.0006 (11) | 0.0141 (12) | −0.0006 (12) |
C23 | 0.0217 (15) | 0.0276 (16) | 0.0233 (16) | −0.0001 (12) | 0.0105 (12) | −0.0010 (13) |
C22 | 0.0253 (15) | 0.0151 (14) | 0.0263 (16) | 0.0023 (11) | 0.0154 (13) | 0.0051 (12) |
C7 | 0.0198 (14) | 0.0198 (14) | 0.0191 (15) | 0.0005 (11) | 0.0108 (12) | 0.0007 (12) |
C13 | 0.0173 (14) | 0.0172 (14) | 0.0310 (17) | 0.0005 (11) | 0.0129 (12) | 0.0066 (13) |
C12 | 0.0180 (14) | 0.0164 (14) | 0.0232 (16) | 0.0009 (11) | 0.0105 (12) | 0.0038 (12) |
C2 | 0.0213 (15) | 0.0261 (16) | 0.0173 (15) | −0.0061 (12) | 0.0064 (12) | −0.0021 (12) |
C8 | 0.0260 (16) | 0.0299 (16) | 0.0204 (16) | −0.0006 (13) | 0.0105 (13) | −0.0041 (13) |
C15 | 0.0220 (15) | 0.0240 (16) | 0.0236 (16) | −0.0015 (12) | 0.0080 (12) | −0.0008 (12) |
C10 | 0.0171 (14) | 0.0299 (16) | 0.0219 (16) | 0.0008 (12) | 0.0052 (12) | −0.0010 (13) |
C17 | 0.0223 (15) | 0.0200 (15) | 0.0345 (18) | 0.0022 (12) | 0.0162 (13) | 0.0059 (13) |
C14 | 0.0191 (14) | 0.0148 (14) | 0.0234 (16) | 0.0008 (11) | 0.0119 (12) | 0.0030 (12) |
C9 | 0.0245 (15) | 0.0362 (18) | 0.0184 (16) | −0.0022 (13) | 0.0043 (12) | −0.0046 (13) |
C16 | 0.0164 (14) | 0.0281 (17) | 0.0368 (19) | 0.0009 (12) | 0.0063 (13) | 0.0050 (14) |
C21 | 0.0393 (18) | 0.0216 (16) | 0.0265 (18) | 0.0007 (13) | 0.0165 (14) | 0.0055 (13) |
C18 | 0.0248 (16) | 0.0272 (17) | 0.055 (2) | 0.0093 (13) | 0.0221 (16) | 0.0100 (16) |
C20 | 0.061 (2) | 0.0200 (16) | 0.037 (2) | 0.0024 (15) | 0.0318 (18) | 0.0028 (14) |
C19 | 0.049 (2) | 0.0232 (17) | 0.059 (3) | 0.0109 (15) | 0.042 (2) | 0.0075 (17) |
C27 | 0.0381 (19) | 0.0350 (19) | 0.044 (2) | −0.0129 (15) | 0.0093 (16) | 0.0012 (16) |
C24 | 0.056 (3) | 0.076 (3) | 0.036 (2) | 0.014 (2) | 0.0115 (19) | −0.019 (2) |
C28 | 0.0207 (17) | 0.039 (2) | 0.096 (3) | 0.0010 (15) | 0.0124 (19) | 0.018 (2) |
C25 | 0.057 (2) | 0.054 (3) | 0.049 (2) | 0.027 (2) | 0.029 (2) | −0.005 (2) |
Cl3 | 0.0253 (4) | 0.0231 (4) | 0.0345 (4) | −0.0010 (3) | 0.0093 (3) | 0.0036 (3) |
O32 | 0.0667 (18) | 0.0310 (13) | 0.0356 (15) | −0.0074 (12) | 0.0161 (13) | −0.0069 (11) |
O31 | 0.0470 (14) | 0.0308 (13) | 0.0329 (13) | 0.0096 (10) | 0.0157 (11) | 0.0021 (10) |
O33 | 0.0415 (14) | 0.0339 (13) | 0.0506 (16) | −0.0068 (11) | 0.0132 (12) | 0.0131 (12) |
O34 | 0.0236 (13) | 0.0569 (17) | 0.078 (2) | −0.0019 (12) | 0.0051 (12) | 0.0301 (16) |
Cl2 | 0.035 (2) | 0.0304 (14) | 0.0318 (15) | −0.0038 (10) | 0.0015 (10) | 0.0079 (10) |
O6 | 0.058 (3) | 0.061 (3) | 0.031 (2) | 0.020 (3) | 0.003 (2) | 0.013 (2) |
O7 | 0.030 (3) | 0.042 (3) | 0.030 (3) | 0.001 (2) | −0.0012 (19) | 0.010 (2) |
O8 | 0.0562 (19) | 0.0482 (18) | 0.068 (2) | −0.0204 (14) | −0.0038 (16) | 0.0132 (16) |
O9 | 0.087 (5) | 0.054 (3) | 0.069 (4) | 0.010 (3) | 0.049 (3) | 0.000 (3) |
Cl1 | 0.023 (3) | 0.027 (2) | 0.041 (4) | −0.0043 (18) | 0.012 (3) | 0.003 (2) |
O10 | 0.108 (9) | 0.052 (5) | 0.063 (5) | 0.023 (6) | 0.013 (5) | 0.026 (5) |
O11 | 0.021 (3) | 0.048 (7) | 0.111 (12) | −0.004 (3) | 0.006 (4) | −0.003 (8) |
O13 | 0.019 (3) | 0.030 (2) | 0.052 (5) | 0.000 (2) | 0.000 (3) | 0.001 (3) |
O12 | 0.054 (6) | 0.084 (7) | 0.052 (4) | 0.032 (5) | 0.018 (5) | −0.005 (5) |
Geometric parameters (Å, º) top
Cu1—O2 | 1.960 (2) | C13—C14 | 1.477 (4) |
Cu1—O1 | 1.958 (2) | C2—H2 | 0.9300 |
Cu1—O4 | 2.211 (2) | C8—H8 | 0.9300 |
Cu1—N2 | 2.003 (2) | C8—C9 | 1.367 (4) |
Cu1—N1 | 1.997 (2) | C15—H15 | 0.9300 |
Cu1—O31 | 2.713 (2) | C15—C14 | 1.414 (4) |
O2—C26 | 1.255 (4) | C15—C16 | 1.367 (4) |
O1—C23 | 1.264 (4) | C10—H10 | 0.9300 |
O3—C11 | 1.375 (3) | C10—C9 | 1.393 (4) |
O3—C13 | 1.355 (4) | C17—C16 | 1.399 (5) |
O4—H4A | 0.9082 | C17—C18 | 1.425 (4) |
O4—H4B | 0.9052 | C9—H9 | 0.9300 |
N2—C5 | 1.356 (4) | C16—H16 | 0.9300 |
N2—C1 | 1.332 (4) | C21—H21 | 0.9300 |
N1—C6 | 1.357 (4) | C21—C20 | 1.368 (5) |
N1—C10 | 1.328 (4) | C18—H18 | 0.9300 |
N4—C13 | 1.303 (4) | C18—C19 | 1.372 (6) |
N4—C12 | 1.386 (3) | C20—H20 | 0.9300 |
N7—C26 | 1.300 (4) | C20—C19 | 1.396 (6) |
N7—C27 | 1.449 (4) | C19—H19 | 0.9300 |
N7—C28 | 1.442 (4) | C27—H27A | 0.9600 |
N5—C22 | 1.372 (4) | C27—H27B | 0.9600 |
N5—C14 | 1.319 (4) | C27—H27C | 0.9600 |
O5—H5A | 0.8521 | C24—H24A | 0.9600 |
O5—H5B | 0.8497 | C24—H24B | 0.9600 |
N6—C23 | 1.298 (4) | C24—H24C | 0.9600 |
N6—C24 | 1.425 (5) | C28—H28A | 0.9600 |
N6—C25 | 1.451 (4) | C28—H28B | 0.9600 |
C5—C6 | 1.449 (4) | C28—H28C | 0.9600 |
C5—C4 | 1.404 (4) | C25—H25A | 0.9600 |
C6—C7 | 1.405 (4) | C25—H25B | 0.9600 |
C4—C3 | 1.406 (4) | C25—H25C | 0.9600 |
C4—C12 | 1.437 (4) | Cl3—O32 | 1.449 (3) |
C1—H1 | 0.9300 | Cl3—O31 | 1.428 (2) |
C1—C2 | 1.395 (4) | Cl3—O33 | 1.430 (2) |
C26—H26 | 0.9300 | Cl3—O34 | 1.427 (3) |
C3—H3 | 0.9300 | Cl2—O6 | 1.452 (6) |
C3—C2 | 1.373 (4) | Cl2—O7 | 1.460 (6) |
C11—C7 | 1.424 (4) | Cl2—O8 | 1.410 (7) |
C11—C12 | 1.366 (4) | Cl2—O9 | 1.435 (7) |
C23—H23 | 0.9300 | Cl1—O10 | 1.380 (13) |
C22—C17 | 1.421 (4) | Cl1—O11 | 1.358 (12) |
C22—C21 | 1.407 (5) | Cl1—O13 | 1.423 (11) |
C7—C8 | 1.405 (4) | Cl1—O12 | 1.365 (12) |
| | | |
O2—Cu1—O4 | 84.60 (9) | C9—C8—C7 | 118.8 (3) |
O2—Cu1—N2 | 168.83 (9) | C9—C8—H8 | 120.6 |
O2—Cu1—N1 | 93.56 (9) | C14—C15—H15 | 120.9 |
O2—Cu1—O31 | 90.49 (8) | C16—C15—H15 | 120.9 |
O1—Cu1—O2 | 91.45 (8) | C16—C15—C14 | 118.2 (3) |
O1—Cu1—O4 | 92.21 (8) | N1—C10—H10 | 118.9 |
O1—Cu1—N2 | 91.07 (9) | N1—C10—C9 | 122.2 (3) |
O1—Cu1—N1 | 168.47 (9) | C9—C10—H10 | 118.9 |
O1—Cu1—O31 | 81.37 (8) | C22—C17—C18 | 118.3 (3) |
O4—Cu1—O31 | 171.83 (8) | C16—C17—C22 | 118.2 (3) |
N2—Cu1—O4 | 106.18 (9) | C16—C17—C18 | 123.5 (3) |
N2—Cu1—O31 | 79.14 (8) | N5—C14—C13 | 117.1 (3) |
N1—Cu1—O4 | 98.60 (9) | N5—C14—C15 | 124.6 (3) |
N1—Cu1—N2 | 82.09 (9) | C15—C14—C13 | 118.3 (3) |
N1—Cu1—O31 | 88.20 (8) | C8—C9—C10 | 120.1 (3) |
C26—O2—Cu1 | 125.1 (2) | C8—C9—H9 | 120.0 |
C23—O1—Cu1 | 118.96 (19) | C10—C9—H9 | 120.0 |
C13—O3—C11 | 103.7 (2) | C15—C16—C17 | 119.8 (3) |
Cu1—O4—H4A | 112.6 | C15—C16—H16 | 120.1 |
Cu1—O4—H4B | 111.5 | C17—C16—H16 | 120.1 |
H4A—O4—H4B | 106.5 | C22—C21—H21 | 119.6 |
C5—N2—Cu1 | 112.50 (19) | C20—C21—C22 | 120.7 (3) |
C1—N2—Cu1 | 127.96 (19) | C20—C21—H21 | 119.6 |
C1—N2—C5 | 118.4 (2) | C17—C18—H18 | 119.7 |
C6—N1—Cu1 | 112.56 (18) | C19—C18—C17 | 120.5 (3) |
C10—N1—Cu1 | 128.20 (19) | C19—C18—H18 | 119.7 |
C10—N1—C6 | 118.9 (2) | C21—C20—H20 | 119.7 |
C13—N4—C12 | 104.1 (2) | C21—C20—C19 | 120.6 (3) |
C26—N7—C27 | 121.5 (3) | C19—C20—H20 | 119.7 |
C26—N7—C28 | 121.5 (3) | C18—C19—C20 | 120.4 (3) |
C28—N7—C27 | 116.9 (3) | C18—C19—H19 | 119.8 |
C14—N5—C22 | 117.3 (3) | C20—C19—H19 | 119.8 |
H5A—O5—H5B | 104.4 | N7—C27—H27A | 109.5 |
C23—N6—C24 | 120.7 (3) | N7—C27—H27B | 109.5 |
C23—N6—C25 | 121.8 (3) | N7—C27—H27C | 109.5 |
C24—N6—C25 | 117.5 (3) | H27A—C27—H27B | 109.5 |
N2—C5—C6 | 115.5 (2) | H27A—C27—H27C | 109.5 |
N2—C5—C4 | 122.7 (3) | H27B—C27—H27C | 109.5 |
C4—C5—C6 | 121.8 (2) | N6—C24—H24A | 109.5 |
N1—C6—C5 | 116.0 (2) | N6—C24—H24B | 109.5 |
N1—C6—C7 | 121.9 (3) | N6—C24—H24C | 109.5 |
C7—C6—C5 | 122.1 (2) | H24A—C24—H24B | 109.5 |
C5—C4—C3 | 117.6 (2) | H24A—C24—H24C | 109.5 |
C5—C4—C12 | 115.4 (3) | H24B—C24—H24C | 109.5 |
C3—C4—C12 | 126.9 (3) | N7—C28—H28A | 109.5 |
N2—C1—H1 | 118.8 | N7—C28—H28B | 109.5 |
N2—C1—C2 | 122.4 (3) | N7—C28—H28C | 109.5 |
C2—C1—H1 | 118.8 | H28A—C28—H28B | 109.5 |
O2—C26—N7 | 123.6 (3) | H28A—C28—H28C | 109.5 |
O2—C26—H26 | 118.2 | H28B—C28—H28C | 109.5 |
N7—C26—H26 | 118.2 | N6—C25—H25A | 109.5 |
C4—C3—H3 | 120.5 | N6—C25—H25B | 109.5 |
C2—C3—C4 | 119.1 (3) | N6—C25—H25C | 109.5 |
C2—C3—H3 | 120.5 | H25A—C25—H25B | 109.5 |
O3—C11—C7 | 126.8 (3) | H25A—C25—H25C | 109.5 |
C12—C11—O3 | 108.1 (2) | H25B—C25—H25C | 109.5 |
C12—C11—C7 | 125.1 (2) | O31—Cl3—O32 | 108.18 (15) |
O1—C23—N6 | 123.9 (3) | O31—Cl3—O33 | 110.89 (15) |
O1—C23—H23 | 118.1 | O33—Cl3—O32 | 110.35 (15) |
N6—C23—H23 | 118.1 | O34—Cl3—O32 | 107.92 (18) |
N5—C22—C17 | 122.0 (3) | O34—Cl3—O31 | 109.61 (17) |
N5—C22—C21 | 118.7 (3) | O34—Cl3—O33 | 109.82 (16) |
C21—C22—C17 | 119.3 (3) | Cl3—O31—Cu1 | 133.25 (13) |
C6—C7—C11 | 114.0 (3) | O6—Cl2—O7 | 106.6 (5) |
C6—C7—C8 | 118.1 (3) | O8—Cl2—O6 | 117.4 (5) |
C8—C7—C11 | 127.9 (3) | O8—Cl2—O7 | 110.9 (5) |
O3—C13—C14 | 118.6 (3) | O8—Cl2—O9 | 109.2 (5) |
N4—C13—O3 | 115.2 (2) | O9—Cl2—O6 | 109.0 (5) |
N4—C13—C14 | 126.2 (3) | O9—Cl2—O7 | 102.7 (6) |
N4—C12—C4 | 129.5 (3) | O10—Cl1—O13 | 103.4 (10) |
C11—C12—N4 | 109.0 (2) | O11—Cl1—O10 | 122.3 (12) |
C11—C12—C4 | 121.5 (3) | O11—Cl1—O13 | 101.0 (11) |
C1—C2—H2 | 120.1 | O11—Cl1—O12 | 118.5 (13) |
C3—C2—C1 | 119.8 (3) | O12—Cl1—O10 | 100.2 (10) |
C3—C2—H2 | 120.1 | O12—Cl1—O13 | 110.5 (9) |
C7—C8—H8 | 120.6 | | |
| | | |
Cu1—O2—C26—N7 | −164.5 (2) | C3—C4—C12—C11 | −179.0 (3) |
Cu1—O1—C23—N6 | 166.9 (2) | C11—O3—C13—N4 | 0.5 (3) |
Cu1—N2—C5—C6 | −10.3 (3) | C11—O3—C13—C14 | −178.7 (2) |
Cu1—N2—C5—C4 | 167.4 (2) | C11—C7—C8—C9 | −176.7 (3) |
Cu1—N2—C1—C2 | −164.2 (2) | C22—N5—C14—C13 | 179.0 (2) |
Cu1—N1—C6—C5 | 6.4 (3) | C22—N5—C14—C15 | 0.3 (4) |
Cu1—N1—C6—C7 | −172.7 (2) | C22—C17—C16—C15 | 0.2 (4) |
Cu1—N1—C10—C9 | 174.1 (2) | C22—C17—C18—C19 | 0.6 (4) |
O3—C11—C7—C6 | −177.9 (3) | C22—C21—C20—C19 | 1.3 (5) |
O3—C11—C7—C8 | 0.7 (5) | C7—C11—C12—N4 | −178.0 (3) |
O3—C11—C12—N4 | 0.3 (3) | C7—C11—C12—C4 | 2.0 (4) |
O3—C11—C12—C4 | −179.6 (2) | C7—C8—C9—C10 | 0.6 (5) |
O3—C13—C14—N5 | 0.4 (4) | C13—O3—C11—C7 | 177.8 (3) |
O3—C13—C14—C15 | 179.2 (2) | C13—O3—C11—C12 | −0.5 (3) |
N2—C5—C6—N1 | 2.6 (4) | C13—N4—C12—C4 | 179.9 (3) |
N2—C5—C6—C7 | −178.3 (2) | C13—N4—C12—C11 | 0.0 (3) |
N2—C5—C4—C3 | −1.2 (4) | C12—N4—C13—O3 | −0.3 (3) |
N2—C5—C4—C12 | −179.2 (2) | C12—N4—C13—C14 | 178.8 (3) |
N2—C1—C2—C3 | −1.1 (4) | C12—C4—C3—C2 | −179.6 (3) |
N1—C6—C7—C11 | 175.9 (2) | C12—C11—C7—C6 | 0.1 (4) |
N1—C6—C7—C8 | −2.7 (4) | C12—C11—C7—C8 | 178.7 (3) |
N1—C10—C9—C8 | −2.2 (5) | C10—N1—C6—C5 | −179.6 (3) |
N4—C13—C14—N5 | −178.7 (3) | C10—N1—C6—C7 | 1.3 (4) |
N4—C13—C14—C15 | 0.0 (4) | C17—C22—C21—C20 | −0.4 (4) |
N5—C22—C17—C16 | −0.7 (4) | C17—C18—C19—C20 | 0.3 (5) |
N5—C22—C17—C18 | 179.1 (3) | C14—N5—C22—C17 | 0.5 (4) |
N5—C22—C21—C20 | 179.9 (3) | C14—N5—C22—C21 | −179.8 (2) |
C5—N2—C1—C2 | 2.6 (4) | C14—C15—C16—C17 | 0.5 (4) |
C5—C6—C7—C11 | −3.1 (4) | C16—C15—C14—N5 | −0.8 (4) |
C5—C6—C7—C8 | 178.2 (3) | C16—C15—C14—C13 | −179.5 (3) |
C5—C4—C3—C2 | 2.7 (4) | C16—C17—C18—C19 | −179.6 (3) |
C5—C4—C12—N4 | 178.9 (3) | C21—C22—C17—C16 | 179.6 (3) |
C5—C4—C12—C11 | −1.2 (4) | C21—C22—C17—C18 | −0.6 (4) |
C6—N1—C10—C9 | 1.2 (4) | C21—C20—C19—C18 | −1.3 (5) |
C6—C5—C4—C3 | 176.3 (2) | C18—C17—C16—C15 | −179.7 (3) |
C6—C5—C4—C12 | −1.8 (4) | C27—N7—C26—O2 | −179.8 (3) |
C6—C7—C8—C9 | 1.7 (4) | C24—N6—C23—O1 | 0.4 (5) |
C4—C5—C6—N1 | −175.0 (2) | C28—N7—C26—O2 | 0.9 (5) |
C4—C5—C6—C7 | 4.1 (4) | C25—N6—C23—O1 | 178.9 (3) |
C4—C3—C2—C1 | −1.6 (4) | O32—Cl3—O31—Cu1 | 46.4 (2) |
C1—N2—C5—C6 | −179.0 (2) | O33—Cl3—O31—Cu1 | 167.57 (17) |
C1—N2—C5—C4 | −1.4 (4) | O34—Cl3—O31—Cu1 | −71.0 (2) |
C3—C4—C12—N4 | 1.1 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···O5 | 0.91 | 1.94 | 2.808 (3) | 160 |
O4—H4B···O32i | 0.91 | 1.96 | 2.782 (3) | 151 |
O5—H5A···O11ii | 0.85 | 2.02 | 2.862 (18) | 170 |
O5—H5B···O10 | 0.85 | 1.95 | 2.790 (13) | 171 |
O5—H5A···O7ii | 0.85 | 2.11 | 2.954 (7) | 174 |
O5—H5B···O6 | 0.85 | 2.07 | 2.905 (7) | 165 |
Symmetry codes: (i) x, y−1, z; (ii) −x+3/2, −y+1/2, −z+1. |
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