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The new copper(II) complex dichloridobis(4-{[3-(pyridin-2-yl-κ
N)-1
H-pyrazol-1-yl-κ
N2]methyl}benzoic acid)copper(II) methanol sesquisolvate hemihydrate, [CuCl
2L2]·1.5CH
3OH·0.5H
2O, (
1), has been synthesized from CuCl
2·2H
2O and the ligand 4-{[3-(pyridin-2-yl)-1
H-pyrazol-1-yl]methyl}benzoic acid (
L, C
15H
11N
3O
2). The complex was characterized by elemental analysis, Fourier transform IR spectroscopy, electrospray ionization mass spectrometry and single-crystal X-ray diffraction. Two chloride ligands and two bidentate
L ligands coordinate the Cu
II centre in
1 in a Jahn–Teller-distorted octahedral geometry of rather unusual configuration: a chloride substituent and a pyrazole N atom of an
N,
N′-chelating ligand occupy the more distant axial positions. Classical O—H
![...](/logos/entities/ctdot_rmgif.gif)
O hydrogen bonds and O—H
![...](/logos/entities/ctdot_rmgif.gif)
Cl interactions link neighbouring complex molecules and cocrystallized methanol molecules into chains that propagate parallel to the
b direction. The title compound shows intriguing bioactivity: the effects of
1 on the enzymatic activity of protein tyrosine phosphatase 1B (PTP1B) and on the viability of human breast cancer cells of cell line MCF7 were evaluated. Complex
1, with an IC
50 value of 0.51 µ
M, can efficiently inhibit PTP1B activity. An enzyme kinetic assay suggests that
1 inhibits PTP1B in a noncompetitive manner. A fluorescence titration assay indicates that
1 has a strong affinity for PTP1B, with a binding constant of 4.39 × 10
6 M−1. Complex
1 may also effectively decrease the viability of MCF7 cells in an extent comparable to that of cisplatin (IC
50 = 6.3 µ
M). The new copper complex therefore represents a promising PTP1B inhibitor and an efficient antiproliferation reagent against MCF7 cells.
Supporting information
CCDC reference: 2010406
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b).
Dichloridobis(4-{[3-(pyridin-2-yl-
κN)-1
H-pyrazol-1-yl-
κN2]methyl}benzoic acid)copper(II) methanol sesquisolvate
hemihydrate
top
Crystal data top
[CuCl2(C15H11N3O2)2]·1.5CH4O·0.5H2O | Z = 2 |
Mr = 722.05 | F(000) = 742 |
Triclinic, P1 | Dx = 1.490 Mg m−3 |
a = 8.4226 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.4978 (8) Å | Cell parameters from 6208 reflections |
c = 15.2060 (8) Å | θ = 3.0–27.6° |
α = 74.260 (2)° | µ = 0.90 mm−1 |
β = 82.358 (2)° | T = 297 K |
γ = 75.781 (2)° | Block, green |
V = 1608.84 (16) Å3 | 0.28 × 0.26 × 0.25 mm |
Data collection top
Bruker APEXII CCD diffractometer | 5359 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.039 |
φ and ω scans | θmax = 28.2°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −11→11 |
Tmin = 0.678, Tmax = 0.746 | k = −17→17 |
17964 measured reflections | l = −20→18 |
7757 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.112 | w = 1/[σ2(Fo2) + (0.039P)2 + 1.P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.005 |
7757 reflections | Δρmax = 0.47 e Å−3 |
447 parameters | Δρmin = −0.38 e Å−3 |
7 restraints | |
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 | 0.37742 (4) | −0.01188 (3) | 0.26715 (2) | 0.03278 (11) | |
Cl1 | 0.27265 (9) | −0.15825 (6) | 0.39997 (5) | 0.04631 (19) | |
Cl2 | 0.15234 (9) | 0.06521 (7) | 0.17762 (5) | 0.0470 (2) | |
O1 | 0.9310 (4) | −0.4878 (3) | 0.1717 (3) | 0.1239 (15) | |
O2 | 1.1126 (5) | −0.3983 (3) | 0.0933 (3) | 0.1181 (13) | |
H2A | 1.135 (8) | −0.441 (4) | 0.058 (4) | 0.177* | |
O3 | 0.2450 (5) | 0.5122 (3) | 0.3271 (2) | 0.0966 (10) | |
H3A | 0.223 (7) | 0.546 (4) | 0.368 (3) | 0.145* | |
O4 | 0.4949 (4) | 0.5360 (3) | 0.3315 (2) | 0.1038 (11) | |
N1 | 0.3018 (3) | 0.08863 (17) | 0.34925 (15) | 0.0336 (5) | |
N2 | 0.5944 (3) | −0.03577 (17) | 0.33778 (14) | 0.0318 (5) | |
N3 | 0.7564 (3) | −0.07953 (18) | 0.33099 (15) | 0.0342 (5) | |
N4 | 0.4683 (3) | −0.10692 (18) | 0.18145 (14) | 0.0340 (5) | |
N5 | 0.5556 (3) | 0.08162 (19) | 0.15063 (15) | 0.0392 (6) | |
N6 | 0.6388 (3) | 0.1590 (2) | 0.13135 (17) | 0.0457 (6) | |
C1 | 0.1467 (4) | 0.1408 (2) | 0.3614 (2) | 0.0445 (7) | |
H1 | 0.065102 | 0.128298 | 0.332885 | 0.053* | |
C2 | 0.1037 (4) | 0.2123 (3) | 0.4148 (2) | 0.0527 (8) | |
H2 | −0.005362 | 0.246569 | 0.422720 | 0.063* | |
C3 | 0.2236 (4) | 0.2325 (2) | 0.4562 (2) | 0.0508 (8) | |
H3 | 0.197138 | 0.282065 | 0.491002 | 0.061* | |
C4 | 0.3836 (4) | 0.1785 (2) | 0.44532 (19) | 0.0410 (7) | |
H4 | 0.466643 | 0.190872 | 0.472800 | 0.049* | |
C5 | 0.4186 (3) | 0.1056 (2) | 0.39296 (17) | 0.0324 (6) | |
C6 | 0.5818 (3) | 0.0409 (2) | 0.37963 (17) | 0.0320 (6) | |
C7 | 0.7357 (3) | 0.0453 (2) | 0.40164 (19) | 0.0401 (7) | |
H7 | 0.758914 | 0.091049 | 0.431652 | 0.048* | |
C8 | 0.8440 (4) | −0.0322 (2) | 0.3695 (2) | 0.0420 (7) | |
H8 | 0.957167 | −0.049505 | 0.373299 | 0.050* | |
C9 | 0.8187 (3) | −0.1667 (2) | 0.29030 (18) | 0.0349 (6) | |
C10 | 0.7388 (3) | −0.2486 (2) | 0.30945 (19) | 0.0385 (6) | |
H10 | 0.646072 | −0.248948 | 0.350125 | 0.046* | |
C11 | 0.7991 (4) | −0.3300 (2) | 0.2672 (2) | 0.0441 (7) | |
H11 | 0.747723 | −0.386483 | 0.279874 | 0.053* | |
C12 | 0.9369 (4) | −0.3278 (3) | 0.2054 (2) | 0.0493 (8) | |
C13 | 1.0157 (4) | −0.2455 (3) | 0.1891 (2) | 0.0508 (8) | |
H13 | 1.109086 | −0.244951 | 0.148888 | 0.061* | |
C14 | 0.9582 (3) | −0.1645 (3) | 0.2313 (2) | 0.0440 (7) | |
H14 | 1.011918 | −0.109305 | 0.220413 | 0.053* | |
C15 | 0.9943 (5) | −0.4111 (4) | 0.1548 (3) | 0.0735 (12) | |
C16 | 0.4143 (4) | −0.1947 (2) | 0.1910 (2) | 0.0412 (7) | |
H16 | 0.336933 | −0.211973 | 0.238808 | 0.049* | |
C17 | 0.4682 (4) | −0.2608 (3) | 0.1330 (2) | 0.0470 (8) | |
H17 | 0.428295 | −0.321450 | 0.141965 | 0.056* | |
C18 | 0.5818 (4) | −0.2355 (3) | 0.0618 (2) | 0.0497 (8) | |
H18 | 0.620160 | −0.278959 | 0.021947 | 0.060* | |
C19 | 0.6379 (4) | −0.1453 (2) | 0.0503 (2) | 0.0447 (7) | |
H19 | 0.714336 | −0.126814 | 0.002300 | 0.054* | |
C20 | 0.5798 (3) | −0.0821 (2) | 0.11092 (18) | 0.0346 (6) | |
C21 | 0.6357 (3) | 0.0149 (2) | 0.10151 (18) | 0.0373 (6) | |
C22 | 0.7688 (4) | 0.0514 (3) | 0.0481 (2) | 0.0516 (8) | |
H22 | 0.841641 | 0.019594 | 0.007019 | 0.062* | |
C23 | 0.7685 (4) | 0.1427 (3) | 0.0689 (2) | 0.0569 (9) | |
H23 | 0.842477 | 0.185986 | 0.045284 | 0.068* | |
C24 | 0.5821 (4) | 0.2446 (2) | 0.1738 (2) | 0.0500 (8) | |
C25 | 0.6923 (5) | 0.2891 (3) | 0.2012 (2) | 0.0652 (10) | |
H25 | 0.804794 | 0.264624 | 0.191136 | 0.078* | |
C26 | 0.6319 (6) | 0.3711 (3) | 0.2440 (3) | 0.0723 (11) | |
H26 | 0.704617 | 0.402935 | 0.261512 | 0.087* | |
C27 | 0.4642 (6) | 0.4058 (3) | 0.2608 (2) | 0.0625 (10) | |
C28 | 0.3567 (5) | 0.3601 (3) | 0.2330 (2) | 0.0579 (9) | |
H28 | 0.244223 | 0.383853 | 0.243797 | 0.069* | |
C29 | 0.4141 (5) | 0.2795 (2) | 0.1894 (2) | 0.0525 (8) | |
H29 | 0.341022 | 0.248906 | 0.170705 | 0.063* | |
C30 | 0.4062 (7) | 0.4911 (3) | 0.3100 (3) | 0.0738 (12) | |
O5 | 0.1491 (4) | 0.6324 (2) | 0.4403 (2) | 0.0838 (9) | |
H5 | 0.180 (6) | 0.692 (2) | 0.427 (3) | 0.126* | |
C31 | 0.2226 (9) | 0.5699 (4) | 0.5213 (3) | 0.147 (3) | |
H31A | 0.323769 | 0.524833 | 0.505728 | 0.221* | |
H31B | 0.149613 | 0.527499 | 0.557641 | 0.221* | |
H31C | 0.244281 | 0.614774 | 0.555446 | 0.221* | |
O6 | 0.7403 (10) | −0.4787 (5) | 0.0072 (4) | 0.107 (2) | 0.5 |
H6 | 0.778 (8) | −0.474 (8) | 0.055 (5) | 0.161* | 0.5 |
C32 | 0.5670 (11) | −0.4887 (8) | 0.0141 (7) | 0.097 (3) | 0.5 |
H32A | 0.528949 | −0.508411 | 0.077481 | 0.145* | 0.5 |
H32B | 0.560145 | −0.541880 | −0.015413 | 0.145* | 0.5 |
H32C | 0.499824 | −0.422433 | −0.015192 | 0.145* | 0.5 |
O7 | 0.0478 (8) | 0.3356 (6) | 0.0974 (7) | 0.161 (4) | 0.5 |
H7A | 0.033837 | 0.375984 | 0.130687 | 0.241* | 0.5 |
H7B | 0.111077 | 0.350994 | 0.052477 | 0.241* | 0.5 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.02966 (18) | 0.0412 (2) | 0.03133 (18) | −0.00584 (14) | 0.00008 (13) | −0.01833 (14) |
Cl1 | 0.0455 (4) | 0.0564 (5) | 0.0451 (4) | −0.0183 (4) | 0.0042 (3) | −0.0232 (4) |
Cl2 | 0.0368 (4) | 0.0663 (5) | 0.0414 (4) | −0.0102 (4) | −0.0039 (3) | −0.0197 (4) |
O1 | 0.100 (2) | 0.128 (3) | 0.196 (4) | −0.059 (2) | 0.047 (2) | −0.125 (3) |
O2 | 0.108 (3) | 0.129 (3) | 0.142 (3) | −0.034 (2) | 0.053 (2) | −0.097 (3) |
O3 | 0.113 (3) | 0.078 (2) | 0.111 (3) | −0.013 (2) | −0.003 (2) | −0.0551 (19) |
O4 | 0.133 (3) | 0.094 (2) | 0.113 (3) | −0.060 (2) | 0.024 (2) | −0.059 (2) |
N1 | 0.0326 (12) | 0.0383 (13) | 0.0305 (12) | −0.0078 (10) | 0.0032 (10) | −0.0120 (10) |
N2 | 0.0312 (11) | 0.0373 (13) | 0.0296 (12) | −0.0087 (10) | 0.0008 (9) | −0.0130 (10) |
N3 | 0.0307 (11) | 0.0416 (13) | 0.0340 (12) | −0.0111 (10) | −0.0001 (10) | −0.0139 (10) |
N4 | 0.0317 (12) | 0.0432 (14) | 0.0294 (12) | −0.0059 (11) | −0.0018 (9) | −0.0151 (10) |
N5 | 0.0432 (14) | 0.0439 (14) | 0.0321 (13) | −0.0142 (12) | 0.0002 (11) | −0.0092 (11) |
N6 | 0.0511 (15) | 0.0479 (15) | 0.0407 (14) | −0.0168 (13) | −0.0007 (12) | −0.0112 (12) |
C1 | 0.0400 (16) | 0.0507 (19) | 0.0437 (17) | −0.0056 (15) | 0.0028 (13) | −0.0199 (14) |
C2 | 0.0462 (18) | 0.056 (2) | 0.051 (2) | 0.0057 (16) | 0.0042 (15) | −0.0240 (16) |
C3 | 0.068 (2) | 0.0417 (18) | 0.0412 (18) | −0.0016 (17) | 0.0036 (16) | −0.0212 (14) |
C4 | 0.0581 (19) | 0.0377 (16) | 0.0324 (15) | −0.0134 (15) | −0.0017 (14) | −0.0153 (12) |
C5 | 0.0402 (15) | 0.0329 (14) | 0.0244 (13) | −0.0117 (12) | 0.0033 (11) | −0.0071 (11) |
C6 | 0.0385 (15) | 0.0363 (15) | 0.0241 (13) | −0.0142 (12) | 0.0001 (11) | −0.0080 (11) |
C7 | 0.0428 (16) | 0.0458 (17) | 0.0398 (16) | −0.0159 (14) | −0.0050 (13) | −0.0176 (13) |
C8 | 0.0352 (15) | 0.0512 (18) | 0.0457 (17) | −0.0154 (14) | −0.0051 (13) | −0.0159 (14) |
C9 | 0.0312 (14) | 0.0407 (16) | 0.0335 (15) | −0.0034 (12) | −0.0045 (11) | −0.0134 (12) |
C10 | 0.0340 (15) | 0.0450 (17) | 0.0375 (16) | −0.0095 (13) | −0.0006 (12) | −0.0123 (13) |
C11 | 0.0415 (16) | 0.0421 (17) | 0.0526 (19) | −0.0100 (14) | −0.0104 (14) | −0.0144 (14) |
C12 | 0.0377 (16) | 0.058 (2) | 0.059 (2) | −0.0030 (15) | −0.0043 (15) | −0.0324 (17) |
C13 | 0.0313 (15) | 0.072 (2) | 0.058 (2) | −0.0121 (16) | 0.0070 (14) | −0.0342 (17) |
C14 | 0.0342 (15) | 0.0562 (19) | 0.0485 (18) | −0.0142 (14) | 0.0031 (13) | −0.0232 (15) |
C15 | 0.059 (2) | 0.086 (3) | 0.092 (3) | −0.020 (2) | 0.010 (2) | −0.054 (3) |
C16 | 0.0393 (16) | 0.0501 (18) | 0.0392 (16) | −0.0108 (14) | −0.0004 (13) | −0.0195 (14) |
C17 | 0.0541 (19) | 0.0474 (18) | 0.0472 (18) | −0.0103 (15) | −0.0086 (15) | −0.0230 (15) |
C18 | 0.0537 (19) | 0.056 (2) | 0.0418 (18) | 0.0021 (16) | −0.0053 (15) | −0.0281 (15) |
C19 | 0.0421 (16) | 0.057 (2) | 0.0326 (15) | −0.0021 (15) | 0.0024 (13) | −0.0168 (14) |
C20 | 0.0300 (13) | 0.0434 (16) | 0.0283 (14) | −0.0002 (12) | −0.0058 (11) | −0.0107 (12) |
C21 | 0.0337 (14) | 0.0473 (17) | 0.0279 (14) | −0.0043 (13) | −0.0024 (12) | −0.0086 (12) |
C22 | 0.0396 (17) | 0.065 (2) | 0.0503 (19) | −0.0130 (16) | 0.0105 (15) | −0.0190 (16) |
C23 | 0.050 (2) | 0.071 (2) | 0.053 (2) | −0.0281 (18) | 0.0099 (16) | −0.0147 (18) |
C24 | 0.070 (2) | 0.0432 (18) | 0.0380 (17) | −0.0212 (17) | 0.0000 (16) | −0.0055 (14) |
C25 | 0.074 (3) | 0.066 (2) | 0.064 (2) | −0.031 (2) | 0.000 (2) | −0.0193 (19) |
C26 | 0.104 (3) | 0.065 (3) | 0.065 (2) | −0.045 (2) | −0.003 (2) | −0.023 (2) |
C27 | 0.098 (3) | 0.046 (2) | 0.047 (2) | −0.028 (2) | 0.005 (2) | −0.0094 (16) |
C28 | 0.078 (2) | 0.0443 (19) | 0.048 (2) | −0.0170 (18) | 0.0026 (18) | −0.0075 (15) |
C29 | 0.071 (2) | 0.0443 (19) | 0.0442 (18) | −0.0192 (17) | −0.0010 (17) | −0.0092 (15) |
C30 | 0.111 (4) | 0.051 (2) | 0.063 (3) | −0.032 (3) | 0.006 (2) | −0.0138 (19) |
O5 | 0.105 (2) | 0.0609 (18) | 0.087 (2) | −0.0198 (17) | 0.0028 (18) | −0.0243 (17) |
C31 | 0.223 (7) | 0.094 (4) | 0.079 (4) | 0.045 (4) | −0.016 (4) | −0.014 (3) |
O6 | 0.174 (7) | 0.084 (4) | 0.073 (4) | −0.018 (5) | 0.000 (4) | −0.046 (4) |
C32 | 0.124 (10) | 0.084 (7) | 0.072 (6) | −0.023 (7) | 0.006 (7) | −0.006 (5) |
O7 | 0.088 (5) | 0.120 (6) | 0.313 (13) | −0.027 (5) | 0.021 (6) | −0.131 (8) |
Geometric parameters (Å, º) top
Cu1—N1 | 2.022 (2) | C11—H11 | 0.9300 |
Cu1—N4 | 2.022 (2) | C12—C13 | 1.380 (4) |
Cu1—N2 | 2.155 (2) | C12—C15 | 1.482 (5) |
Cu1—Cl2 | 2.3407 (8) | C13—C14 | 1.371 (4) |
Cu1—N5 | 2.448 (2) | C13—H13 | 0.9300 |
Cu1—Cl1 | 2.6418 (9) | C14—H14 | 0.9300 |
O1—C15 | 1.229 (5) | C16—C17 | 1.377 (4) |
O2—C15 | 1.282 (5) | C16—H16 | 0.9300 |
O2—H2A | 0.861 (19) | C17—C18 | 1.375 (4) |
O3—C30 | 1.322 (5) | C17—H17 | 0.9300 |
O3—H3A | 0.844 (19) | C18—C19 | 1.371 (4) |
O4—C30 | 1.195 (5) | C18—H18 | 0.9300 |
N1—C1 | 1.339 (3) | C19—C20 | 1.385 (4) |
N1—C5 | 1.353 (3) | C19—H19 | 0.9300 |
N2—C6 | 1.332 (3) | C20—C21 | 1.462 (4) |
N2—N3 | 1.350 (3) | C21—C22 | 1.404 (4) |
N3—C8 | 1.358 (3) | C22—C23 | 1.352 (5) |
N3—C9 | 1.431 (3) | C22—H22 | 0.9300 |
N4—C16 | 1.336 (4) | C23—H23 | 0.9300 |
N4—C20 | 1.355 (3) | C24—C25 | 1.381 (5) |
N5—C21 | 1.325 (3) | C24—C29 | 1.387 (5) |
N5—N6 | 1.344 (3) | C25—C26 | 1.391 (5) |
N6—C23 | 1.365 (4) | C25—H25 | 0.9300 |
N6—C24 | 1.424 (4) | C26—C27 | 1.387 (6) |
C1—C2 | 1.377 (4) | C26—H26 | 0.9300 |
C1—H1 | 0.9300 | C27—C28 | 1.376 (5) |
C2—C3 | 1.374 (5) | C27—C30 | 1.489 (5) |
C2—H2 | 0.9300 | C28—C29 | 1.381 (4) |
C3—C4 | 1.378 (4) | C28—H28 | 0.9300 |
C3—H3 | 0.9300 | C29—H29 | 0.9300 |
C4—C5 | 1.382 (3) | O5—C31 | 1.412 (5) |
C4—H4 | 0.9300 | O5—H5 | 0.871 (19) |
C5—C6 | 1.457 (4) | C31—H31A | 0.9600 |
C6—C7 | 1.399 (4) | C31—H31B | 0.9600 |
C7—C8 | 1.361 (4) | C31—H31C | 0.9600 |
C7—H7 | 0.9300 | O6—C32 | 1.487 (8) |
C8—H8 | 0.9300 | O6—H6 | 0.85 (2) |
C9—C10 | 1.378 (4) | C32—H32A | 0.9600 |
C9—C14 | 1.382 (4) | C32—H32B | 0.9600 |
C10—C11 | 1.379 (4) | C32—H32C | 0.9600 |
C10—H10 | 0.9300 | O7—H7A | 0.8193 |
C11—C12 | 1.394 (4) | O7—H7B | 0.8208 |
| | | |
N1—Cu1—N4 | 175.47 (9) | C11—C12—C15 | 120.0 (3) |
N1—Cu1—N2 | 78.11 (8) | C14—C13—C12 | 120.9 (3) |
N4—Cu1—N2 | 99.13 (8) | C14—C13—H13 | 119.5 |
N1—Cu1—Cl2 | 92.71 (7) | C12—C13—H13 | 119.5 |
N4—Cu1—Cl2 | 89.06 (6) | C13—C14—C9 | 118.5 (3) |
N2—Cu1—Cl2 | 163.07 (6) | C13—C14—H14 | 120.8 |
N1—Cu1—N5 | 101.40 (8) | C9—C14—H14 | 120.8 |
N4—Cu1—N5 | 74.38 (9) | O1—C15—O2 | 122.7 (4) |
N2—Cu1—N5 | 77.00 (8) | O1—C15—C12 | 121.1 (4) |
Cl2—Cu1—N5 | 91.15 (6) | O2—C15—C12 | 116.2 (4) |
N1—Cu1—Cl1 | 88.13 (6) | N4—C16—C17 | 122.9 (3) |
N4—Cu1—Cl1 | 95.50 (7) | N4—C16—H16 | 118.5 |
N2—Cu1—Cl1 | 90.11 (6) | C17—C16—H16 | 118.5 |
Cl2—Cu1—Cl1 | 103.92 (3) | C18—C17—C16 | 118.9 (3) |
N5—Cu1—Cl1 | 161.84 (6) | C18—C17—H17 | 120.6 |
C15—O2—H2A | 116 (4) | C16—C17—H17 | 120.6 |
C30—O3—H3A | 108 (4) | C19—C18—C17 | 119.2 (3) |
C1—N1—C5 | 118.3 (2) | C19—C18—H18 | 120.4 |
C1—N1—Cu1 | 124.86 (19) | C17—C18—H18 | 120.4 |
C5—N1—Cu1 | 116.85 (17) | C18—C19—C20 | 119.4 (3) |
C6—N2—N3 | 105.3 (2) | C18—C19—H19 | 120.3 |
C6—N2—Cu1 | 110.71 (17) | C20—C19—H19 | 120.3 |
N3—N2—Cu1 | 139.38 (16) | N4—C20—C19 | 121.6 (3) |
N2—N3—C8 | 111.1 (2) | N4—C20—C21 | 116.9 (2) |
N2—N3—C9 | 121.8 (2) | C19—C20—C21 | 121.5 (3) |
C8—N3—C9 | 127.1 (2) | N5—C21—C22 | 111.0 (3) |
C16—N4—C20 | 118.0 (2) | N5—C21—C20 | 118.7 (2) |
C16—N4—Cu1 | 120.38 (18) | C22—C21—C20 | 130.3 (3) |
C20—N4—Cu1 | 121.59 (19) | C23—C22—C21 | 105.4 (3) |
C21—N5—N6 | 105.2 (2) | C23—C22—H22 | 127.3 |
C21—N5—Cu1 | 106.93 (18) | C21—C22—H22 | 127.3 |
N6—N5—Cu1 | 144.08 (18) | C22—C23—N6 | 106.9 (3) |
N5—N6—C23 | 111.5 (3) | C22—C23—H23 | 126.6 |
N5—N6—C24 | 119.0 (2) | N6—C23—H23 | 126.6 |
C23—N6—C24 | 129.4 (3) | C25—C24—C29 | 121.1 (3) |
N1—C1—C2 | 122.3 (3) | C25—C24—N6 | 120.5 (3) |
N1—C1—H1 | 118.9 | C29—C24—N6 | 118.3 (3) |
C2—C1—H1 | 118.9 | C24—C25—C26 | 118.8 (4) |
C3—C2—C1 | 119.4 (3) | C24—C25—H25 | 120.6 |
C3—C2—H2 | 120.3 | C26—C25—H25 | 120.6 |
C1—C2—H2 | 120.3 | C27—C26—C25 | 120.5 (4) |
C2—C3—C4 | 119.1 (3) | C27—C26—H26 | 119.7 |
C2—C3—H3 | 120.4 | C25—C26—H26 | 119.7 |
C4—C3—H3 | 120.4 | C28—C27—C26 | 119.7 (3) |
C3—C4—C5 | 118.9 (3) | C28—C27—C30 | 121.9 (4) |
C3—C4—H4 | 120.5 | C26—C27—C30 | 118.4 (4) |
C5—C4—H4 | 120.5 | C27—C28—C29 | 120.7 (4) |
N1—C5—C4 | 122.0 (3) | C27—C28—H28 | 119.7 |
N1—C5—C6 | 114.2 (2) | C29—C28—H28 | 119.7 |
C4—C5—C6 | 123.8 (3) | C28—C29—C24 | 119.2 (3) |
N2—C6—C7 | 111.2 (2) | C28—C29—H29 | 120.4 |
N2—C6—C5 | 117.4 (2) | C24—C29—H29 | 120.4 |
C7—C6—C5 | 131.4 (3) | O4—C30—O3 | 123.5 (4) |
C8—C7—C6 | 105.0 (2) | O4—C30—C27 | 124.0 (5) |
C8—C7—H7 | 127.5 | O3—C30—C27 | 112.6 (4) |
C6—C7—H7 | 127.5 | C31—O5—H5 | 107 (4) |
N3—C8—C7 | 107.5 (3) | O5—C31—H31A | 109.5 |
N3—C8—H8 | 126.3 | O5—C31—H31B | 109.5 |
C7—C8—H8 | 126.3 | H31A—C31—H31B | 109.5 |
C10—C9—C14 | 122.1 (3) | O5—C31—H31C | 109.5 |
C10—C9—N3 | 120.1 (2) | H31A—C31—H31C | 109.5 |
C14—C9—N3 | 117.8 (2) | H31B—C31—H31C | 109.5 |
C9—C10—C11 | 118.8 (3) | C32—O6—H6 | 118 (6) |
C9—C10—H10 | 120.6 | O6—C32—H32A | 109.5 |
C11—C10—H10 | 120.6 | O6—C32—H32B | 109.5 |
C10—C11—C12 | 120.0 (3) | H32A—C32—H32B | 109.5 |
C10—C11—H11 | 120.0 | O6—C32—H32C | 109.5 |
C12—C11—H11 | 120.0 | H32A—C32—H32C | 109.5 |
C13—C12—C11 | 119.7 (3) | H32B—C32—H32C | 109.5 |
C13—C12—C15 | 120.2 (3) | H7A—O7—H7B | 112.3 |
| | | |
C6—N2—N3—C8 | 1.1 (3) | C13—C12—C15—O1 | 176.3 (4) |
Cu1—N2—N3—C8 | 152.9 (2) | C11—C12—C15—O1 | −6.2 (6) |
C6—N2—N3—C9 | 179.2 (2) | C13—C12—C15—O2 | −3.6 (6) |
Cu1—N2—N3—C9 | −29.0 (4) | C11—C12—C15—O2 | 173.9 (4) |
C21—N5—N6—C23 | 1.3 (3) | C20—N4—C16—C17 | 0.6 (4) |
Cu1—N5—N6—C23 | 154.2 (3) | Cu1—N4—C16—C17 | 178.1 (2) |
C21—N5—N6—C24 | 179.7 (3) | N4—C16—C17—C18 | −0.4 (5) |
Cu1—N5—N6—C24 | −27.4 (5) | C16—C17—C18—C19 | −0.2 (5) |
C5—N1—C1—C2 | 1.6 (4) | C17—C18—C19—C20 | 0.4 (5) |
Cu1—N1—C1—C2 | −176.7 (2) | C16—N4—C20—C19 | −0.4 (4) |
N1—C1—C2—C3 | 1.0 (5) | Cu1—N4—C20—C19 | −177.8 (2) |
C1—C2—C3—C4 | −1.8 (5) | C16—N4—C20—C21 | 179.4 (2) |
C2—C3—C4—C5 | 0.1 (5) | Cu1—N4—C20—C21 | 2.0 (3) |
C1—N1—C5—C4 | −3.4 (4) | C18—C19—C20—N4 | −0.1 (4) |
Cu1—N1—C5—C4 | 175.1 (2) | C18—C19—C20—C21 | −179.9 (3) |
C1—N1—C5—C6 | 176.7 (2) | N6—N5—C21—C22 | −1.8 (3) |
Cu1—N1—C5—C6 | −4.9 (3) | Cu1—N5—C21—C22 | −165.6 (2) |
C3—C4—C5—N1 | 2.6 (4) | N6—N5—C21—C20 | 177.0 (2) |
C3—C4—C5—C6 | −177.5 (3) | Cu1—N5—C21—C20 | 13.2 (3) |
N3—N2—C6—C7 | −1.3 (3) | N4—C20—C21—N5 | −11.7 (4) |
Cu1—N2—C6—C7 | −162.05 (18) | C19—C20—C21—N5 | 168.1 (3) |
N3—N2—C6—C5 | 177.5 (2) | N4—C20—C21—C22 | 166.8 (3) |
Cu1—N2—C6—C5 | 16.7 (3) | C19—C20—C21—C22 | −13.4 (5) |
N1—C5—C6—N2 | −8.8 (3) | N5—C21—C22—C23 | 1.6 (4) |
C4—C5—C6—N2 | 171.3 (2) | C20—C21—C22—C23 | −177.0 (3) |
N1—C5—C6—C7 | 169.7 (3) | C21—C22—C23—N6 | −0.7 (4) |
C4—C5—C6—C7 | −10.3 (5) | N5—N6—C23—C22 | −0.4 (4) |
N2—C6—C7—C8 | 1.0 (3) | C24—N6—C23—C22 | −178.5 (3) |
C5—C6—C7—C8 | −177.6 (3) | N5—N6—C24—C25 | 142.7 (3) |
N2—N3—C8—C7 | −0.5 (3) | C23—N6—C24—C25 | −39.3 (5) |
C9—N3—C8—C7 | −178.5 (3) | N5—N6—C24—C29 | −35.3 (4) |
C6—C7—C8—N3 | −0.2 (3) | C23—N6—C24—C29 | 142.7 (3) |
N2—N3—C9—C10 | −42.3 (4) | C29—C24—C25—C26 | −0.8 (5) |
C8—N3—C9—C10 | 135.5 (3) | N6—C24—C25—C26 | −178.7 (3) |
N2—N3—C9—C14 | 136.9 (3) | C24—C25—C26—C27 | 1.5 (6) |
C8—N3—C9—C14 | −45.3 (4) | C25—C26—C27—C28 | −1.4 (6) |
C14—C9—C10—C11 | −1.0 (4) | C25—C26—C27—C30 | 177.7 (3) |
N3—C9—C10—C11 | 178.2 (3) | C26—C27—C28—C29 | 0.6 (5) |
C9—C10—C11—C12 | −0.9 (4) | C30—C27—C28—C29 | −178.5 (3) |
C10—C11—C12—C13 | 2.1 (5) | C27—C28—C29—C24 | 0.1 (5) |
C10—C11—C12—C15 | −175.4 (3) | C25—C24—C29—C28 | 0.1 (5) |
C11—C12—C13—C14 | −1.4 (5) | N6—C24—C29—C28 | 178.0 (3) |
C15—C12—C13—C14 | 176.1 (3) | C28—C27—C30—O4 | −176.4 (4) |
C12—C13—C14—C9 | −0.4 (5) | C26—C27—C30—O4 | 4.5 (6) |
C10—C9—C14—C13 | 1.6 (4) | C28—C27—C30—O3 | 3.3 (5) |
N3—C9—C14—C13 | −177.6 (3) | C26—C27—C30—O3 | −175.8 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O6i | 0.86 (2) | 1.74 (3) | 2.548 (6) | 156 (6) |
O3—H3A···O5 | 0.84 (2) | 1.76 (2) | 2.598 (4) | 169 (6) |
O5—H5···Cl1ii | 0.87 (2) | 2.26 (2) | 3.126 (3) | 176 (5) |
O6—H6···O1 | 0.85 (2) | 2.27 (3) | 3.107 (8) | 166 (5) |
O7—H7A···O1iii | 0.82 | 2.05 | 2.819 (7) | 155 |
O7—H7B···O6iv | 0.82 | 2.30 | 2.953 (11) | 137 |
Symmetry codes: (i) −x+2, −y−1, −z; (ii) x, y+1, z; (iii) x−1, y+1, z; (iv) −x+1, −y, −z. |
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