Subtle modifications of
N-donor ligands can result in complexes with very different compositions and architectures. In the complex
catena-poly[[bis{1-[(1
H-benzotriazol-1-yl)methyl]-1
H-imidazole-
N3}copper(II)]-
-benzene-1,3-dicarboxylato-
3O1,
O1':
O3], {[Cu(C
8H
4O
4)(C
10H
9N
5)
2(H
2O)]·2H
2O}
n, each Cu
II ion is six-coordinated by two N atoms from two crystallographically independent 1-[(1
H-benzotriazol-1-yl)methyl]-1
H-imidazole (bmi) ligands, by three O atoms from two symmetry-related benzene-1,3-dicarboxylate (bdic
2-) ligands and by one water molecule, leading to a distorted CuN
2O
4 octahedral coordination environment. The Cu
II ions are connected by bridging bdic
2- anions to generate a one-dimensional chain. The bmi ligands coordinate to the Cu
II ions in monodentate modes and are pendant on opposite sides of the main chain. In the crystal, the chains are linked by O-H
O and O-H
N hydrogen bonds, as well as by
-
interactions, into a three-dimensional network. A thermogravimetric analysis was carried out and the fluorescence behaviour of the complex was also investigated.
Supporting information
CCDC reference: 1528580
Data collection: CrystalClear (Rigaku/MSC, 2004); cell refinement: CrystalClear (Rigaku/MSC, 2004); data reduction: CrystalClear (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: publCIF (Westrip, 2010).
catena-Poly[[bis{1-[(1
H-benzotriazol-1-yl)methyl]-1
H-1,3-imidazole-
κN3}copper(II)]-µ-benzene-1,3-dicarboxylato-
κ3O1,
O1':
O3]
top
Crystal data top
[Cu(C8H4O4)(C10H9N5)2(H2O)]·2H2O | Z = 2 |
Mr = 680.14 | F(000) = 702 |
Triclinic, P1 | Dx = 1.524 Mg m−3 |
a = 10.174 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.538 (3) Å | Cell parameters from 4516 reflections |
c = 13.665 (3) Å | θ = 1.9–27.9° |
α = 63.45 (3)° | µ = 0.80 mm−1 |
β = 77.06 (3)° | T = 293 K |
γ = 73.02 (3)° | Prism, blue |
V = 1482.5 (7) Å3 | 0.18 × 0.15 × 0.12 mm |
Data collection top
Rigaku Saturn diffractometer | 5802 independent reflections |
Radiation source: fine-focus sealed tube | 4596 reflections with I > 2σ(I) |
Detector resolution: 28.5714 pixels mm-1 | Rint = 0.040 |
ω scans | θmax = 26.0°, θmin = 2.1° |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004) | h = −12→12 |
Tmin = 0.869, Tmax = 0.910 | k = −15→15 |
13759 measured reflections | l = −16→15 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.060 | H-atom parameters constrained |
wR(F2) = 0.148 | w = 1/[σ2(Fo2) + (0.0708P)2 + 0.7087P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
5802 reflections | Δρmax = 0.32 e Å−3 |
415 parameters | Δρmin = −0.38 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 | |
Cu1 | 0.61160 (4) | 0.51451 (4) | 0.75427 (4) | 0.03293 (16) | |
N1 | 0.6490 (3) | 0.3776 (3) | 0.7066 (3) | 0.0350 (7) | |
N2 | 0.7383 (3) | 0.2639 (3) | 0.6135 (3) | 0.0387 (7) | |
N3 | 0.9097 (4) | 0.0941 (3) | 0.5922 (3) | 0.0482 (9) | |
N4 | 0.8460 (5) | −0.0029 (4) | 0.6430 (3) | 0.0628 (11) | |
N5 | 0.9391 (6) | −0.1023 (4) | 0.6806 (4) | 0.0734 (13) | |
N6 | 0.5758 (3) | 0.6575 (3) | 0.7924 (2) | 0.0338 (7) | |
N7 | 0.4985 (3) | 0.7864 (3) | 0.8712 (3) | 0.0353 (7) | |
N8 | 0.3329 (3) | 0.9572 (3) | 0.8948 (3) | 0.0432 (8) | |
N9 | 0.3863 (4) | 1.0591 (3) | 0.8456 (3) | 0.0610 (11) | |
N10 | 0.2872 (4) | 1.1535 (3) | 0.8013 (3) | 0.0586 (10) | |
O1 | 0.8159 (2) | 0.4973 (2) | 0.7517 (2) | 0.0349 (6) | |
O2 | 0.7436 (2) | 0.3855 (2) | 0.9238 (2) | 0.0401 (6) | |
O3 | 1.3136 (3) | 0.5510 (2) | 0.6717 (2) | 0.0465 (7) | |
O4 | 1.4237 (3) | 0.4919 (3) | 0.8185 (2) | 0.0469 (7) | |
O5 | 0.5480 (3) | 0.6575 (2) | 0.5747 (2) | 0.0516 (7) | |
H1W | 0.6055 | 0.6489 | 0.5217 | 0.062* | |
H2W | 0.4754 | 0.6362 | 0.5759 | 0.062* | |
O7 | 0.9522 (5) | 0.5960 (5) | 0.5384 (4) | 0.1276 (18) | |
H5W | 0.9949 | 0.5222 | 0.5697 | 0.153* | |
H6W | 0.8972 | 0.6051 | 0.5924 | 0.153* | |
C1 | 0.8346 (3) | 0.4340 (3) | 0.8542 (3) | 0.0313 (8) | |
C2 | 1.3212 (3) | 0.5034 (3) | 0.7728 (3) | 0.0366 (9) | |
C3 | 0.9705 (3) | 0.4192 (3) | 0.8902 (3) | 0.0307 (8) | |
C4 | 1.0791 (3) | 0.4666 (3) | 0.8153 (3) | 0.0324 (8) | |
H4A | 1.0685 | 0.5083 | 0.7407 | 0.039* | |
C5 | 1.2038 (3) | 0.4517 (3) | 0.8524 (3) | 0.0327 (8) | |
C6 | 1.2179 (4) | 0.3890 (3) | 0.9636 (3) | 0.0395 (9) | |
H6A | 1.3010 | 0.3778 | 0.9885 | 0.047* | |
C7 | 1.1099 (4) | 0.3423 (3) | 1.0392 (3) | 0.0413 (9) | |
H7A | 1.1204 | 0.3006 | 1.1139 | 0.050* | |
C8 | 0.9867 (4) | 0.3590 (3) | 1.0014 (3) | 0.0349 (8) | |
H8A | 0.9138 | 0.3293 | 1.0515 | 0.042* | |
C9 | 0.7484 (4) | 0.3575 (3) | 0.6326 (3) | 0.0375 (9) | |
H9A | 0.8168 | 0.4021 | 0.5980 | 0.045* | |
C10 | 0.5720 (4) | 0.2907 (3) | 0.7367 (3) | 0.0412 (9) | |
H10A | 0.4947 | 0.2820 | 0.7887 | 0.049* | |
C11 | 0.6252 (4) | 0.2214 (4) | 0.6803 (4) | 0.0453 (10) | |
H11A | 0.5924 | 0.1571 | 0.6851 | 0.054* | |
C12 | 0.8283 (5) | 0.2167 (4) | 0.5360 (3) | 0.0482 (10) | |
H12A | 0.8901 | 0.2710 | 0.4908 | 0.058* | |
H12B | 0.7726 | 0.2149 | 0.4879 | 0.058* | |
C13 | 1.0492 (5) | 0.0515 (4) | 0.5976 (3) | 0.0530 (11) | |
C14 | 1.0656 (7) | −0.0733 (5) | 0.6546 (4) | 0.0689 (16) | |
C15 | 1.1968 (8) | −0.1479 (7) | 0.6752 (5) | 0.099 (3) | |
H15A | 1.2082 | −0.2321 | 0.7144 | 0.119* | |
C16 | 1.3063 (8) | −0.0960 (9) | 0.6375 (7) | 0.116 (3) | |
H16A | 1.3944 | −0.1453 | 0.6494 | 0.139* | |
C17 | 1.2907 (6) | 0.0308 (9) | 0.5804 (6) | 0.103 (2) | |
H17A | 1.3690 | 0.0637 | 0.5553 | 0.123* | |
C18 | 1.1600 (5) | 0.1097 (5) | 0.5601 (4) | 0.0693 (14) | |
H18A | 1.1482 | 0.1942 | 0.5244 | 0.083* | |
C19 | 0.4855 (3) | 0.6825 (3) | 0.8693 (3) | 0.0315 (8) | |
H19A | 0.4221 | 0.6358 | 0.9156 | 0.038* | |
C20 | 0.6513 (4) | 0.7482 (3) | 0.7442 (3) | 0.0426 (9) | |
H20A | 0.7232 | 0.7535 | 0.6877 | 0.051* | |
C21 | 0.6034 (4) | 0.8272 (3) | 0.7927 (3) | 0.0434 (9) | |
H21A | 0.6357 | 0.8962 | 0.7760 | 0.052* | |
C22 | 0.4225 (4) | 0.8388 (3) | 0.9492 (3) | 0.0431 (9) | |
H22A | 0.3670 | 0.7835 | 1.0048 | 0.052* | |
H22B | 0.4874 | 0.8478 | 0.9857 | 0.052* | |
C23 | 0.1965 (4) | 0.9868 (3) | 0.8811 (3) | 0.0374 (9) | |
C24 | 0.0958 (4) | 0.9180 (3) | 0.9148 (3) | 0.0409 (9) | |
H24A | 0.1161 | 0.8335 | 0.9536 | 0.049* | |
C25 | −0.0344 (5) | 0.9824 (4) | 0.8874 (3) | 0.0494 (10) | |
H25A | −0.1045 | 0.9402 | 0.9075 | 0.059* | |
C26 | −0.0654 (5) | 1.1096 (4) | 0.8300 (3) | 0.0513 (11) | |
H26A | −0.1559 | 1.1496 | 0.8148 | 0.062* | |
C27 | 0.0323 (5) | 1.1766 (4) | 0.7959 (3) | 0.0504 (11) | |
H27A | 0.0107 | 1.2610 | 0.7569 | 0.060* | |
C28 | 0.1675 (5) | 1.1133 (3) | 0.8218 (3) | 0.0435 (10) | |
O6 | 0.7304 (3) | 0.6158 (3) | 0.4016 (2) | 0.0551 (8) | |
H3W | 0.7139 | 0.6838 | 0.3464 | 0.066* | |
H4W | 0.7171 | 0.5571 | 0.3927 | 0.066* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0176 (2) | 0.0419 (3) | 0.0429 (3) | −0.00510 (17) | −0.00402 (18) | −0.0210 (2) |
N1 | 0.0247 (16) | 0.0396 (16) | 0.0404 (18) | −0.0061 (13) | −0.0065 (13) | −0.0153 (14) |
N2 | 0.0384 (19) | 0.0379 (17) | 0.0392 (18) | −0.0019 (14) | −0.0078 (15) | −0.0175 (14) |
N3 | 0.054 (2) | 0.049 (2) | 0.041 (2) | −0.0012 (17) | −0.0043 (17) | −0.0236 (16) |
N4 | 0.077 (3) | 0.053 (2) | 0.060 (3) | −0.015 (2) | −0.002 (2) | −0.026 (2) |
N5 | 0.103 (4) | 0.051 (2) | 0.061 (3) | −0.005 (2) | −0.008 (3) | −0.027 (2) |
N6 | 0.0246 (15) | 0.0356 (16) | 0.0395 (18) | −0.0069 (12) | −0.0063 (13) | −0.0124 (14) |
N7 | 0.0312 (17) | 0.0312 (15) | 0.0394 (18) | −0.0024 (13) | −0.0046 (14) | −0.0134 (13) |
N8 | 0.042 (2) | 0.0306 (16) | 0.053 (2) | −0.0100 (14) | 0.0033 (16) | −0.0165 (15) |
N9 | 0.051 (2) | 0.042 (2) | 0.081 (3) | −0.0171 (18) | 0.011 (2) | −0.023 (2) |
N10 | 0.056 (2) | 0.0306 (18) | 0.073 (3) | −0.0100 (17) | 0.006 (2) | −0.0131 (17) |
O1 | 0.0197 (12) | 0.0446 (14) | 0.0396 (15) | −0.0071 (10) | −0.0049 (11) | −0.0157 (12) |
O2 | 0.0238 (13) | 0.0505 (15) | 0.0409 (15) | −0.0162 (12) | 0.0013 (11) | −0.0117 (12) |
O3 | 0.0281 (14) | 0.0560 (17) | 0.0495 (18) | −0.0137 (12) | −0.0024 (13) | −0.0146 (14) |
O4 | 0.0186 (13) | 0.0776 (19) | 0.0615 (19) | −0.0153 (13) | 0.0021 (12) | −0.0434 (16) |
O5 | 0.0516 (18) | 0.0569 (17) | 0.0442 (17) | −0.0132 (14) | −0.0007 (14) | −0.0202 (14) |
O7 | 0.114 (4) | 0.156 (4) | 0.102 (4) | −0.071 (4) | 0.041 (3) | −0.042 (3) |
C1 | 0.0203 (17) | 0.0334 (18) | 0.044 (2) | −0.0055 (14) | −0.0029 (16) | −0.0195 (17) |
C2 | 0.0181 (17) | 0.041 (2) | 0.058 (3) | −0.0040 (15) | −0.0016 (17) | −0.0287 (19) |
C3 | 0.0243 (18) | 0.0305 (17) | 0.039 (2) | −0.0056 (14) | −0.0053 (15) | −0.0147 (15) |
C4 | 0.0245 (18) | 0.0358 (18) | 0.038 (2) | −0.0053 (14) | −0.0060 (15) | −0.0162 (16) |
C5 | 0.0218 (17) | 0.0323 (18) | 0.049 (2) | −0.0045 (14) | −0.0042 (16) | −0.0222 (17) |
C6 | 0.0257 (19) | 0.041 (2) | 0.055 (3) | −0.0036 (15) | −0.0161 (18) | −0.0194 (19) |
C7 | 0.040 (2) | 0.039 (2) | 0.045 (2) | −0.0115 (17) | −0.0136 (18) | −0.0114 (17) |
C8 | 0.0298 (19) | 0.0344 (18) | 0.042 (2) | −0.0100 (15) | −0.0029 (16) | −0.0151 (16) |
C9 | 0.031 (2) | 0.0352 (19) | 0.040 (2) | −0.0081 (15) | −0.0039 (17) | −0.0093 (17) |
C10 | 0.028 (2) | 0.041 (2) | 0.055 (3) | −0.0097 (16) | −0.0042 (18) | −0.0190 (19) |
C11 | 0.036 (2) | 0.045 (2) | 0.064 (3) | −0.0109 (18) | −0.007 (2) | −0.028 (2) |
C12 | 0.057 (3) | 0.046 (2) | 0.038 (2) | −0.002 (2) | −0.007 (2) | −0.0196 (19) |
C13 | 0.060 (3) | 0.059 (3) | 0.040 (2) | 0.005 (2) | −0.008 (2) | −0.030 (2) |
C14 | 0.093 (4) | 0.061 (3) | 0.041 (3) | 0.020 (3) | −0.013 (3) | −0.031 (2) |
C15 | 0.109 (6) | 0.111 (5) | 0.059 (4) | 0.054 (4) | −0.037 (4) | −0.053 (4) |
C16 | 0.091 (6) | 0.159 (8) | 0.090 (5) | 0.058 (5) | −0.044 (5) | −0.082 (6) |
C17 | 0.057 (4) | 0.185 (8) | 0.088 (5) | −0.005 (4) | −0.008 (3) | −0.088 (5) |
C18 | 0.055 (3) | 0.096 (4) | 0.063 (3) | −0.005 (3) | −0.006 (3) | −0.045 (3) |
C19 | 0.0243 (18) | 0.0318 (18) | 0.035 (2) | −0.0068 (14) | −0.0054 (15) | −0.0093 (15) |
C20 | 0.034 (2) | 0.043 (2) | 0.043 (2) | −0.0102 (17) | 0.0038 (18) | −0.0131 (18) |
C21 | 0.038 (2) | 0.038 (2) | 0.051 (2) | −0.0128 (17) | −0.0001 (19) | −0.0144 (19) |
C22 | 0.049 (2) | 0.035 (2) | 0.043 (2) | −0.0037 (17) | −0.0064 (19) | −0.0167 (17) |
C23 | 0.045 (2) | 0.0341 (19) | 0.032 (2) | −0.0078 (16) | 0.0037 (17) | −0.0161 (16) |
C24 | 0.048 (2) | 0.039 (2) | 0.039 (2) | −0.0109 (18) | −0.0052 (18) | −0.0172 (17) |
C25 | 0.053 (3) | 0.059 (3) | 0.045 (2) | −0.018 (2) | −0.005 (2) | −0.027 (2) |
C26 | 0.052 (3) | 0.059 (3) | 0.038 (2) | 0.003 (2) | −0.014 (2) | −0.021 (2) |
C27 | 0.061 (3) | 0.039 (2) | 0.039 (2) | 0.001 (2) | −0.003 (2) | −0.0140 (18) |
C28 | 0.054 (3) | 0.033 (2) | 0.038 (2) | −0.0103 (18) | 0.0055 (19) | −0.0142 (17) |
O6 | 0.061 (2) | 0.0498 (17) | 0.0498 (18) | −0.0127 (14) | −0.0056 (15) | −0.0163 (14) |
Geometric parameters (Å, º) top
Cu1—O4i | 1.962 (3) | C5—C6 | 1.382 (5) |
Cu1—N6 | 1.997 (3) | C6—C7 | 1.395 (5) |
Cu1—N1 | 2.006 (3) | C6—H6A | 0.9300 |
Cu1—O1 | 2.020 (2) | C7—C8 | 1.386 (5) |
Cu1—O5 | 2.399 (3) | C7—H7A | 0.9300 |
N1—C9 | 1.315 (5) | C8—H8A | 0.9300 |
N1—C10 | 1.387 (4) | C9—H9A | 0.9300 |
N2—C9 | 1.346 (5) | C10—C11 | 1.335 (6) |
N2—C11 | 1.376 (5) | C10—H10A | 0.9300 |
N2—C12 | 1.456 (5) | C11—H11A | 0.9300 |
N3—C13 | 1.369 (6) | C12—H12A | 0.9700 |
N3—N4 | 1.374 (5) | C12—H12B | 0.9700 |
N3—C12 | 1.457 (5) | C13—C14 | 1.378 (6) |
N4—N5 | 1.293 (6) | C13—C18 | 1.398 (7) |
N5—C14 | 1.366 (7) | C14—C15 | 1.393 (8) |
N6—C19 | 1.320 (5) | C15—C16 | 1.340 (10) |
N6—C20 | 1.389 (5) | C15—H15A | 0.9300 |
N7—C19 | 1.359 (4) | C16—C17 | 1.400 (10) |
N7—C21 | 1.367 (5) | C16—H16A | 0.9300 |
N7—C22 | 1.458 (5) | C17—C18 | 1.405 (8) |
N8—C23 | 1.361 (5) | C17—H17A | 0.9300 |
N8—N9 | 1.362 (4) | C18—H18A | 0.9300 |
N8—C22 | 1.454 (5) | C19—H19A | 0.9300 |
N9—N10 | 1.311 (5) | C20—C21 | 1.349 (5) |
N10—C28 | 1.376 (5) | C20—H20A | 0.9300 |
O1—C1 | 1.290 (4) | C21—H21A | 0.9300 |
O2—C1 | 1.244 (4) | C22—H22A | 0.9700 |
O3—C2 | 1.247 (5) | C22—H22B | 0.9700 |
O4—C2 | 1.274 (4) | C23—C28 | 1.395 (5) |
O4—Cu1ii | 1.962 (3) | C23—C24 | 1.398 (5) |
O5—H1W | 0.8500 | C24—C25 | 1.369 (6) |
O5—H2W | 0.8499 | C24—H24A | 0.9300 |
O7—H5W | 0.8500 | C25—C26 | 1.399 (6) |
O7—H6W | 0.8501 | C25—H25A | 0.9300 |
C1—C3 | 1.504 (5) | C26—C27 | 1.357 (6) |
C2—C5 | 1.507 (5) | C26—H26A | 0.9300 |
C3—C8 | 1.386 (5) | C27—C28 | 1.406 (6) |
C3—C4 | 1.398 (5) | C27—H27A | 0.9300 |
C4—C5 | 1.403 (5) | O6—H3W | 0.8500 |
C4—H4A | 0.9300 | O6—H4W | 0.8499 |
| | | |
O4i—Cu1—N6 | 89.75 (12) | C11—C10—N1 | 110.0 (4) |
O4i—Cu1—N1 | 91.80 (12) | C11—C10—H10A | 125.0 |
N6—Cu1—N1 | 176.62 (12) | N1—C10—H10A | 125.0 |
O4i—Cu1—O1 | 157.13 (11) | C10—C11—N2 | 106.4 (3) |
N6—Cu1—O1 | 88.35 (11) | C10—C11—H11A | 126.8 |
N1—Cu1—O1 | 91.38 (11) | N2—C11—H11A | 126.8 |
O4i—Cu1—O5 | 95.31 (12) | N2—C12—N3 | 111.8 (3) |
N6—Cu1—O5 | 87.41 (11) | N2—C12—H12A | 109.3 |
N1—Cu1—O5 | 89.46 (11) | N3—C12—H12A | 109.3 |
O1—Cu1—O5 | 107.36 (11) | N2—C12—H12B | 109.3 |
C9—N1—C10 | 105.3 (3) | N3—C12—H12B | 109.3 |
C9—N1—Cu1 | 126.2 (3) | H12A—C12—H12B | 107.9 |
C10—N1—Cu1 | 128.3 (3) | N3—C13—C14 | 104.4 (5) |
C9—N2—C11 | 107.1 (3) | N3—C13—C18 | 132.8 (4) |
C9—N2—C12 | 126.9 (3) | C14—C13—C18 | 122.8 (5) |
C11—N2—C12 | 126.0 (3) | N5—C14—C13 | 109.1 (5) |
C13—N3—N4 | 109.2 (4) | N5—C14—C15 | 130.6 (6) |
C13—N3—C12 | 131.1 (4) | C13—C14—C15 | 120.3 (7) |
N4—N3—C12 | 119.5 (4) | C16—C15—C14 | 118.7 (7) |
N5—N4—N3 | 108.5 (4) | C16—C15—H15A | 120.6 |
N4—N5—C14 | 108.8 (4) | C14—C15—H15A | 120.6 |
C19—N6—C20 | 106.5 (3) | C15—C16—C17 | 121.4 (7) |
C19—N6—Cu1 | 128.8 (2) | C15—C16—H16A | 119.3 |
C20—N6—Cu1 | 124.6 (3) | C17—C16—H16A | 119.3 |
C19—N7—C21 | 107.7 (3) | C16—C17—C18 | 121.8 (7) |
C19—N7—C22 | 126.0 (3) | C16—C17—H17A | 119.1 |
C21—N7—C22 | 126.1 (3) | C18—C17—H17A | 119.1 |
C23—N8—N9 | 110.4 (3) | C13—C18—C17 | 114.9 (6) |
C23—N8—C22 | 130.1 (3) | C13—C18—H18A | 122.6 |
N9—N8—C22 | 119.5 (3) | C17—C18—H18A | 122.6 |
N10—N9—N8 | 108.3 (4) | N6—C19—N7 | 110.1 (3) |
N9—N10—C28 | 108.6 (3) | N6—C19—H19A | 125.0 |
C1—O1—Cu1 | 102.2 (2) | N7—C19—H19A | 125.0 |
C2—O4—Cu1ii | 130.1 (3) | C21—C20—N6 | 108.9 (3) |
Cu1—O5—H1W | 114.8 | C21—C20—H20A | 125.6 |
Cu1—O5—H2W | 99.4 | N6—C20—H20A | 125.6 |
H1W—O5—H2W | 108.6 | C20—C21—N7 | 106.9 (3) |
H5W—O7—H6W | 100.7 | C20—C21—H21A | 126.6 |
O2—C1—O1 | 122.0 (3) | N7—C21—H21A | 126.6 |
O2—C1—C3 | 119.3 (3) | N8—C22—N7 | 111.6 (3) |
O1—C1—C3 | 118.7 (3) | N8—C22—H22A | 109.3 |
O3—C2—O4 | 125.5 (3) | N7—C22—H22A | 109.3 |
O3—C2—C5 | 120.4 (3) | N8—C22—H22B | 109.3 |
O4—C2—C5 | 114.1 (4) | N7—C22—H22B | 109.3 |
C8—C3—C4 | 119.3 (3) | H22A—C22—H22B | 108.0 |
C8—C3—C1 | 118.7 (3) | N8—C23—C28 | 104.4 (3) |
C4—C3—C1 | 122.0 (3) | N8—C23—C24 | 133.2 (3) |
C3—C4—C5 | 120.2 (3) | C28—C23—C24 | 122.4 (4) |
C3—C4—H4A | 119.9 | C25—C24—C23 | 116.1 (4) |
C5—C4—H4A | 119.9 | C25—C24—H24A | 122.0 |
C6—C5—C4 | 119.1 (3) | C23—C24—H24A | 122.0 |
C6—C5—C2 | 120.1 (3) | C24—C25—C26 | 122.0 (4) |
C4—C5—C2 | 120.8 (3) | C24—C25—H25A | 119.0 |
C5—C6—C7 | 121.2 (3) | C26—C25—H25A | 119.0 |
C5—C6—H6A | 119.4 | C27—C26—C25 | 122.1 (4) |
C7—C6—H6A | 119.4 | C27—C26—H26A | 118.9 |
C8—C7—C6 | 119.0 (4) | C25—C26—H26A | 118.9 |
C8—C7—H7A | 120.5 | C26—C27—C28 | 117.4 (4) |
C6—C7—H7A | 120.5 | C26—C27—H27A | 121.3 |
C3—C8—C7 | 121.1 (3) | C28—C27—H27A | 121.3 |
C3—C8—H8A | 119.4 | N10—C28—C23 | 108.4 (4) |
C7—C8—H8A | 119.4 | N10—C28—C27 | 131.6 (4) |
N1—C9—N2 | 111.2 (3) | C23—C28—C27 | 120.0 (4) |
N1—C9—H9A | 124.4 | H3W—O6—H4W | 112.9 |
N2—C9—H9A | 124.4 | | |
| | | |
C13—N3—N4—N5 | 0.9 (5) | C12—N3—C13—C18 | 6.1 (8) |
C12—N3—N4—N5 | 175.8 (4) | N4—N5—C14—C13 | 0.0 (5) |
N3—N4—N5—C14 | −0.5 (5) | N4—N5—C14—C15 | −178.8 (5) |
C23—N8—N9—N10 | 0.5 (5) | N3—C13—C14—N5 | 0.6 (5) |
C22—N8—N9—N10 | 179.1 (4) | C18—C13—C14—N5 | 179.6 (4) |
N8—N9—N10—C28 | 0.1 (5) | N3—C13—C14—C15 | 179.5 (4) |
Cu1—O1—C1—O2 | 10.0 (4) | C18—C13—C14—C15 | −1.4 (7) |
Cu1—O1—C1—C3 | −169.7 (2) | N5—C14—C15—C16 | 177.9 (6) |
Cu1ii—O4—C2—O3 | −11.9 (6) | C13—C14—C15—C16 | −0.8 (8) |
Cu1ii—O4—C2—C5 | 167.2 (2) | C14—C15—C16—C17 | 1.4 (10) |
O2—C1—C3—C8 | −4.5 (5) | C15—C16—C17—C18 | 0.1 (10) |
O1—C1—C3—C8 | 175.3 (3) | N3—C13—C18—C17 | −178.5 (5) |
O2—C1—C3—C4 | 177.0 (3) | C14—C13—C18—C17 | 2.8 (7) |
O1—C1—C3—C4 | −3.2 (5) | C16—C17—C18—C13 | −2.1 (8) |
C8—C3—C4—C5 | 1.0 (5) | C20—N6—C19—N7 | 1.0 (4) |
C1—C3—C4—C5 | 179.5 (3) | Cu1—N6—C19—N7 | 177.4 (2) |
C3—C4—C5—C6 | 0.4 (5) | C21—N7—C19—N6 | −0.9 (4) |
C3—C4—C5—C2 | −179.4 (3) | C22—N7—C19—N6 | −176.0 (3) |
O3—C2—C5—C6 | 174.0 (3) | C19—N6—C20—C21 | −0.6 (4) |
O4—C2—C5—C6 | −5.2 (5) | Cu1—N6—C20—C21 | −177.3 (3) |
O3—C2—C5—C4 | −6.3 (5) | N6—C20—C21—N7 | 0.1 (4) |
O4—C2—C5—C4 | 174.5 (3) | C19—N7—C21—C20 | 0.5 (4) |
C4—C5—C6—C7 | −1.0 (5) | C22—N7—C21—C20 | 175.6 (3) |
C2—C5—C6—C7 | 178.8 (3) | C23—N8—C22—N7 | 94.9 (5) |
C5—C6—C7—C8 | 0.3 (6) | N9—N8—C22—N7 | −83.4 (4) |
C4—C3—C8—C7 | −1.7 (5) | C19—N7—C22—N8 | −115.3 (4) |
C1—C3—C8—C7 | 179.7 (3) | C21—N7—C22—N8 | 70.4 (5) |
C6—C7—C8—C3 | 1.1 (6) | N9—N8—C23—C28 | −0.9 (4) |
C10—N1—C9—N2 | 0.5 (4) | C22—N8—C23—C28 | −179.2 (4) |
Cu1—N1—C9—N2 | −175.1 (2) | N9—N8—C23—C24 | −179.9 (4) |
C11—N2—C9—N1 | −0.4 (4) | C22—N8—C23—C24 | 1.8 (7) |
C12—N2—C9—N1 | 179.0 (3) | N8—C23—C24—C25 | 178.1 (4) |
C9—N1—C10—C11 | −0.5 (4) | C28—C23—C24—C25 | −0.8 (6) |
Cu1—N1—C10—C11 | 175.0 (3) | C23—C24—C25—C26 | −0.7 (6) |
N1—C10—C11—N2 | 0.3 (4) | C24—C25—C26—C27 | 1.6 (6) |
C9—N2—C11—C10 | 0.0 (4) | C25—C26—C27—C28 | −0.9 (6) |
C12—N2—C11—C10 | −179.4 (3) | N9—N10—C28—C23 | −0.7 (5) |
C9—N2—C12—N3 | 112.3 (4) | N9—N10—C28—C27 | 177.8 (4) |
C11—N2—C12—N3 | −68.4 (5) | N8—C23—C28—N10 | 0.9 (4) |
C13—N3—C12—N2 | −114.4 (5) | C24—C23—C28—N10 | −179.9 (4) |
N4—N3—C12—N2 | 72.0 (5) | N8—C23—C28—C27 | −177.7 (4) |
N4—N3—C13—C14 | −0.9 (4) | C24—C23—C28—C27 | 1.4 (6) |
C12—N3—C13—C14 | −175.0 (4) | C26—C27—C28—N10 | −178.8 (4) |
N4—N3—C13—C18 | −179.8 (5) | C26—C27—C28—C23 | −0.5 (6) |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H1W···O6 | 0.85 | 1.96 | 2.808 (4) | 174 |
O7—H6W···O1 | 0.85 | 2.11 | 2.814 (5) | 139 |
O5—H2W···O3i | 0.85 | 2.09 | 2.844 (4) | 147 |
O7—H5W···O7iii | 0.85 | 2.41 | 2.876 (11) | 115 |
O6—H3W···N10iv | 0.85 | 2.13 | 2.973 (5) | 169 |
O6—H4W···O3iii | 0.85 | 2.04 | 2.864 (4) | 165 |
Symmetry codes: (i) x−1, y, z; (iii) −x+2, −y+1, −z+1; (iv) −x+1, −y+2, −z+1. |