The title complex, [Cu
2(C
16H
10NO
2)
4(H
2O)
2], has a centrosymmetric wheel-shaped dinuclear structure in which two symmetry-related Cu
II centers are bridged by four carboxylate groups of distinct 2-phenylquinoline-4-carboxylate (phqc) ligands, the Cu—Cu separation being 2.6507 (12) Å. Each Cu
II center is five-coordinated by four O atoms of carboxylate groups in the basal plane and one O atom of a water molecule in the apical position. In addition, the dinuclear molecules are linked by intermolecular O—H
N hydrogen bonds to form a one-dimensional supramolecular chain.
Supporting information
CCDC reference: 289644
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.046
- wR factor = 0.123
- Data-to-parameter ratio = 13.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor O1W - H1 ... ?
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.20
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.77 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C1 .. 5.34 su
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.
Diaquatetrakis(µ-2-phenylquinoline-4-carboxylato-
κ2O:
O')dicopper(II)(Cu—Cu)
top
Crystal data top
[Cu2(C16H10NO2)4(H2O)2] | Z = 1 |
Mr = 1156.11 | F(000) = 594 |
Triclinic, P1 | Dx = 1.488 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2800 (17) Å | Cell parameters from 10366 reflections |
b = 10.668 (2) Å | θ = 3.1–27.5° |
c = 15.501 (3) Å | µ = 0.89 mm−1 |
α = 86.62 (3)° | T = 293 K |
β = 85.99 (3)° | Block, blue |
γ = 70.92 (3)° | 0.14 × 0.10 × 0.10 mm |
V = 1289.9 (4) Å3 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 4730 independent reflections |
Radiation source: fine-focus sealed tube | 3963 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
Detector resolution: 10.00 pixels mm-1 | θmax = 25.5°, θmin = 3.1° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −12→11 |
Tmin = 0.885, Tmax = 0.916 | l = −18→18 |
10554 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0735P)2 + 0.2379P] where P = (Fo2 + 2Fc2)/3 |
4730 reflections | (Δ/σ)max = 0.001 |
361 parameters | Δρmax = 1.04 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.35053 (4) | 0.57927 (3) | 0.03088 (2) | 0.02788 (14) | |
N1 | 0.2023 (3) | −0.0251 (2) | 0.05574 (16) | 0.0323 (5) | |
N2 | 0.7388 (4) | 0.3508 (3) | 0.41677 (17) | 0.0441 (7) | |
C1 | 0.3682 (4) | 0.3182 (3) | 0.01931 (19) | 0.0339 (7) | |
C2 | 0.3060 (4) | 0.1994 (3) | 0.0301 (2) | 0.0334 (6) | |
C3 | 0.3049 (4) | 0.1239 (3) | −0.04222 (19) | 0.0333 (7) | |
C4 | 0.3536 (5) | 0.1528 (3) | −0.1278 (2) | 0.0457 (8) | |
H4A | 0.3932 | 0.2246 | −0.1395 | 0.055* | |
C5 | 0.3437 (5) | 0.0774 (4) | −0.1940 (2) | 0.0539 (9) | |
H5A | 0.3782 | 0.0970 | −0.2502 | 0.065* | |
C6 | 0.2813 (5) | −0.0300 (4) | −0.1774 (2) | 0.0496 (9) | |
H6A | 0.2717 | −0.0794 | −0.2231 | 0.060* | |
C7 | 0.2352 (4) | −0.0627 (3) | −0.0958 (2) | 0.0388 (7) | |
H7A | 0.1961 | −0.1349 | −0.0858 | 0.047* | |
C8 | 0.2463 (4) | 0.0128 (3) | −0.02581 (19) | 0.0321 (6) | |
C9 | 0.2075 (4) | 0.0459 (3) | 0.1222 (2) | 0.0345 (7) | |
C10 | 0.1684 (4) | −0.0016 (3) | 0.2096 (2) | 0.0395 (7) | |
C11 | 0.2256 (5) | −0.1376 (3) | 0.2316 (2) | 0.0460 (8) | |
H11A | 0.2868 | −0.1979 | 0.1905 | 0.055* | |
C12 | 0.1913 (6) | −0.1827 (4) | 0.3142 (3) | 0.0609 (11) | |
H12A | 0.2315 | −0.2730 | 0.3288 | 0.073* | |
C13 | 0.0980 (6) | −0.0943 (5) | 0.3748 (3) | 0.0683 (13) | |
H13A | 0.0741 | −0.1250 | 0.4300 | 0.082* | |
C14 | 0.0402 (6) | 0.0393 (5) | 0.3538 (3) | 0.0619 (11) | |
H14A | −0.0240 | 0.0989 | 0.3946 | 0.074* | |
C15 | 0.0772 (5) | 0.0853 (4) | 0.2722 (2) | 0.0503 (9) | |
H15A | 0.0402 | 0.1761 | 0.2591 | 0.060* | |
C16 | 0.2550 (4) | 0.1629 (3) | 0.1097 (2) | 0.0363 (7) | |
H16A | 0.2509 | 0.2145 | 0.1566 | 0.044* | |
C17 | 0.5961 (4) | 0.4535 (3) | 0.15281 (19) | 0.0331 (7) | |
C18 | 0.6535 (4) | 0.4176 (3) | 0.24328 (19) | 0.0358 (7) | |
C19 | 0.8013 (4) | 0.4379 (3) | 0.27233 (19) | 0.0379 (7) | |
C20 | 0.9123 (5) | 0.4905 (4) | 0.2201 (2) | 0.0484 (8) | |
H20A | 0.8928 | 0.5106 | 0.1618 | 0.058* | |
C21 | 1.0478 (5) | 0.5121 (4) | 0.2544 (3) | 0.0588 (10) | |
H21A | 1.1188 | 0.5482 | 0.2196 | 0.071* | |
C22 | 1.0806 (5) | 0.4798 (4) | 0.3424 (3) | 0.0585 (10) | |
H22A | 1.1730 | 0.4951 | 0.3653 | 0.070* | |
C23 | 0.9784 (5) | 0.4266 (4) | 0.3941 (2) | 0.0514 (9) | |
H23A | 1.0022 | 0.4050 | 0.4519 | 0.062* | |
C24 | 0.8370 (4) | 0.4037 (3) | 0.3610 (2) | 0.0404 (7) | |
C25 | 0.6043 (4) | 0.3306 (3) | 0.3869 (2) | 0.0414 (7) | |
C26 | 0.4987 (5) | 0.2749 (3) | 0.4495 (2) | 0.0453 (8) | |
C27 | 0.4772 (6) | 0.3113 (4) | 0.5342 (2) | 0.0602 (10) | |
H27A | 0.5320 | 0.3680 | 0.5522 | 0.072* | |
C28 | 0.3745 (7) | 0.2644 (5) | 0.5933 (3) | 0.0750 (13) | |
H28A | 0.3568 | 0.2925 | 0.6499 | 0.090* | |
C29 | 0.2991 (6) | 0.1763 (6) | 0.5680 (3) | 0.0807 (15) | |
H29A | 0.2328 | 0.1428 | 0.6079 | 0.097* | |
C30 | 0.3216 (7) | 0.1382 (6) | 0.4849 (3) | 0.0888 (18) | |
H30A | 0.2704 | 0.0786 | 0.4679 | 0.107* | |
C31 | 0.4207 (6) | 0.1875 (5) | 0.4249 (3) | 0.0707 (13) | |
H31A | 0.4345 | 0.1614 | 0.3679 | 0.085* | |
C32 | 0.5560 (5) | 0.3651 (3) | 0.3009 (2) | 0.0419 (8) | |
H32A | 0.4578 | 0.3523 | 0.2830 | 0.050* | |
O1 | 0.2677 (3) | 0.4262 (2) | 0.04389 (15) | 0.0426 (5) | |
O2 | 0.5172 (3) | 0.29631 (19) | −0.01271 (15) | 0.0402 (5) | |
O3 | 0.4461 (3) | 0.5301 (2) | 0.14534 (13) | 0.0435 (5) | |
O4 | 0.7001 (3) | 0.4007 (2) | 0.09265 (13) | 0.0415 (5) | |
O1W | 0.1156 (3) | 0.73465 (18) | 0.06693 (13) | 0.0358 (5) | |
H1 | 0.0145 | 0.7522 | 0.0762 | 0.043* | |
H2 | 0.1297 | 0.8087 | 0.0683 | 0.043* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0352 (2) | 0.0254 (2) | 0.0282 (2) | −0.01726 (15) | −0.00477 (14) | 0.00434 (13) |
N1 | 0.0367 (14) | 0.0270 (12) | 0.0373 (14) | −0.0164 (10) | −0.0034 (11) | 0.0035 (10) |
N2 | 0.0516 (18) | 0.0504 (16) | 0.0339 (14) | −0.0217 (13) | −0.0081 (12) | 0.0069 (12) |
C1 | 0.0414 (18) | 0.0346 (16) | 0.0343 (15) | −0.0246 (14) | −0.0086 (13) | 0.0100 (13) |
C2 | 0.0357 (16) | 0.0247 (14) | 0.0448 (17) | −0.0171 (12) | −0.0051 (13) | 0.0058 (12) |
C3 | 0.0350 (16) | 0.0315 (15) | 0.0391 (16) | −0.0192 (12) | −0.0067 (13) | 0.0088 (12) |
C4 | 0.062 (2) | 0.0435 (18) | 0.0430 (19) | −0.0336 (16) | −0.0144 (16) | 0.0137 (15) |
C5 | 0.077 (3) | 0.062 (2) | 0.0355 (18) | −0.043 (2) | −0.0062 (17) | 0.0098 (16) |
C6 | 0.069 (2) | 0.053 (2) | 0.0379 (18) | −0.0319 (18) | −0.0138 (17) | −0.0006 (15) |
C7 | 0.0446 (18) | 0.0343 (16) | 0.0442 (18) | −0.0214 (14) | −0.0097 (14) | 0.0029 (13) |
C8 | 0.0337 (16) | 0.0252 (14) | 0.0406 (16) | −0.0143 (12) | −0.0080 (13) | 0.0070 (12) |
C9 | 0.0364 (17) | 0.0297 (15) | 0.0421 (17) | −0.0177 (12) | −0.0029 (13) | 0.0036 (13) |
C10 | 0.0443 (19) | 0.0411 (17) | 0.0440 (18) | −0.0289 (14) | −0.0038 (14) | 0.0026 (14) |
C11 | 0.065 (2) | 0.0409 (18) | 0.0408 (18) | −0.0299 (17) | −0.0052 (16) | 0.0052 (14) |
C12 | 0.089 (3) | 0.058 (2) | 0.050 (2) | −0.045 (2) | −0.012 (2) | 0.0164 (19) |
C13 | 0.090 (3) | 0.097 (3) | 0.040 (2) | −0.064 (3) | −0.009 (2) | 0.018 (2) |
C14 | 0.067 (3) | 0.082 (3) | 0.044 (2) | −0.035 (2) | 0.0049 (19) | −0.0067 (19) |
C15 | 0.060 (2) | 0.049 (2) | 0.047 (2) | −0.0251 (17) | 0.0007 (17) | −0.0026 (16) |
C16 | 0.0458 (18) | 0.0324 (15) | 0.0382 (17) | −0.0235 (13) | −0.0021 (14) | 0.0010 (13) |
C17 | 0.0436 (18) | 0.0338 (15) | 0.0302 (15) | −0.0237 (13) | −0.0069 (13) | 0.0040 (12) |
C18 | 0.0453 (18) | 0.0340 (15) | 0.0297 (15) | −0.0151 (13) | −0.0068 (13) | 0.0046 (12) |
C19 | 0.0447 (18) | 0.0378 (16) | 0.0329 (16) | −0.0151 (13) | −0.0066 (13) | 0.0017 (13) |
C20 | 0.056 (2) | 0.056 (2) | 0.0393 (18) | −0.0274 (17) | −0.0077 (16) | 0.0063 (15) |
C21 | 0.056 (2) | 0.077 (3) | 0.054 (2) | −0.038 (2) | −0.0058 (18) | 0.0089 (19) |
C22 | 0.054 (2) | 0.076 (3) | 0.057 (2) | −0.036 (2) | −0.0132 (19) | 0.001 (2) |
C23 | 0.059 (2) | 0.062 (2) | 0.0405 (19) | −0.0276 (18) | −0.0196 (17) | 0.0031 (16) |
C24 | 0.0485 (19) | 0.0410 (17) | 0.0336 (16) | −0.0171 (14) | −0.0075 (14) | 0.0036 (13) |
C25 | 0.049 (2) | 0.0436 (18) | 0.0342 (17) | −0.0188 (15) | −0.0046 (14) | 0.0061 (14) |
C26 | 0.048 (2) | 0.050 (2) | 0.0393 (18) | −0.0193 (16) | −0.0077 (15) | 0.0154 (15) |
C27 | 0.085 (3) | 0.053 (2) | 0.044 (2) | −0.027 (2) | 0.0010 (19) | 0.0127 (17) |
C28 | 0.097 (4) | 0.074 (3) | 0.048 (2) | −0.026 (3) | 0.011 (2) | 0.016 (2) |
C29 | 0.069 (3) | 0.112 (4) | 0.068 (3) | −0.046 (3) | −0.009 (2) | 0.042 (3) |
C30 | 0.094 (4) | 0.121 (4) | 0.082 (3) | −0.079 (4) | −0.034 (3) | 0.044 (3) |
C31 | 0.087 (3) | 0.098 (3) | 0.048 (2) | −0.060 (3) | −0.021 (2) | 0.024 (2) |
C32 | 0.049 (2) | 0.0466 (18) | 0.0356 (17) | −0.0234 (15) | −0.0117 (14) | 0.0083 (14) |
O1 | 0.0461 (13) | 0.0295 (11) | 0.0571 (14) | −0.0212 (10) | 0.0073 (11) | −0.0014 (10) |
O2 | 0.0395 (13) | 0.0290 (11) | 0.0589 (14) | −0.0205 (9) | −0.0050 (11) | 0.0018 (10) |
O3 | 0.0475 (14) | 0.0500 (13) | 0.0309 (11) | −0.0133 (11) | −0.0051 (10) | 0.0060 (10) |
O4 | 0.0464 (14) | 0.0476 (13) | 0.0310 (11) | −0.0152 (10) | −0.0086 (10) | 0.0010 (10) |
O1W | 0.0452 (13) | 0.0192 (9) | 0.0440 (12) | −0.0128 (8) | −0.0005 (10) | 0.0027 (8) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.962 (2) | C14—H14A | 0.9300 |
Cu1—O2i | 1.976 (2) | C15—H15A | 0.9300 |
Cu1—O3 | 1.966 (2) | C16—H16A | 0.9300 |
Cu1—O4i | 1.973 (2) | C17—O4 | 1.250 (4) |
Cu1—O1W | 2.167 (2) | C17—O3 | 1.253 (4) |
Cu1—Cu1i | 2.6507 (12) | C17—C18 | 1.500 (4) |
N1—C9 | 1.325 (4) | C18—C32 | 1.378 (4) |
N1—C8 | 1.365 (4) | C18—C19 | 1.418 (4) |
N2—C25 | 1.320 (4) | C19—C20 | 1.412 (5) |
N2—C24 | 1.367 (4) | C19—C24 | 1.428 (4) |
C1—O1 | 1.243 (4) | C20—C21 | 1.364 (5) |
C1—O2 | 1.250 (4) | C20—H20A | 0.9300 |
C1—C2 | 1.513 (4) | C21—C22 | 1.411 (5) |
C2—C16 | 1.354 (4) | C21—H21A | 0.9300 |
C2—C3 | 1.420 (4) | C22—C23 | 1.358 (5) |
C3—C4 | 1.406 (4) | C22—H22A | 0.9300 |
C3—C8 | 1.425 (4) | C23—C24 | 1.407 (5) |
C4—C5 | 1.363 (5) | C23—H23A | 0.9300 |
C4—H4A | 0.9300 | C25—C32 | 1.411 (4) |
C5—C6 | 1.408 (5) | C25—C26 | 1.487 (5) |
C5—H5A | 0.9300 | C26—C27 | 1.375 (5) |
C6—C7 | 1.354 (5) | C26—C31 | 1.379 (5) |
C6—H6A | 0.9300 | C27—C28 | 1.389 (6) |
C7—C8 | 1.414 (4) | C27—H27A | 0.9300 |
C7—H7A | 0.9300 | C28—C29 | 1.374 (7) |
C9—C16 | 1.425 (4) | C28—H28A | 0.9300 |
C9—C10 | 1.471 (4) | C29—C30 | 1.356 (7) |
C10—C15 | 1.385 (5) | C29—H29A | 0.9300 |
C10—C11 | 1.400 (5) | C30—C31 | 1.391 (6) |
C11—C12 | 1.385 (5) | C30—H30A | 0.9300 |
C11—H11A | 0.9300 | C31—H31A | 0.9300 |
C12—C13 | 1.377 (6) | C32—H32A | 0.9300 |
C12—H12A | 0.9300 | O2—Cu1i | 1.976 (2) |
C13—C14 | 1.374 (6) | O4—Cu1i | 1.973 (2) |
C13—H13A | 0.9300 | O1W—H1 | 0.8001 |
C14—C15 | 1.380 (5) | O1W—H2 | 0.8374 |
| | | |
O1—Cu1—O1W | 99.22 (9) | C14—C15—H15A | 119.5 |
O1—Cu1—O2i | 167.50 (9) | C10—C15—H15A | 119.5 |
O1—Cu1—O3 | 88.27 (10) | C2—C16—C9 | 120.5 (3) |
O1—Cu1—O4i | 89.97 (10) | C2—C16—H16A | 119.7 |
O2i—Cu1—O1W | 93.24 (8) | C9—C16—H16A | 119.7 |
O3—Cu1—O1W | 99.58 (9) | O4—C17—O3 | 126.5 (3) |
O3—Cu1—O2i | 88.61 (10) | O4—C17—C18 | 117.0 (3) |
O3—Cu1—O4i | 167.74 (9) | O3—C17—C18 | 116.5 (3) |
O4i—Cu1—O1W | 92.67 (9) | C32—C18—C19 | 118.8 (3) |
O4i—Cu1—O2i | 90.51 (10) | C32—C18—C17 | 118.3 (3) |
O1—Cu1—Cu1i | 89.10 (7) | C19—C18—C17 | 122.9 (3) |
O3—Cu1—Cu1i | 85.69 (8) | C20—C19—C18 | 124.6 (3) |
O4i—Cu1—Cu1i | 82.15 (8) | C20—C19—C24 | 118.7 (3) |
O2i—Cu1—Cu1i | 78.59 (7) | C18—C19—C24 | 116.8 (3) |
O1W—Cu1—Cu1i | 170.23 (5) | C21—C20—C19 | 120.7 (3) |
C9—N1—C8 | 119.7 (2) | C21—C20—H20A | 119.7 |
C25—N2—C24 | 118.2 (3) | C19—C20—H20A | 119.7 |
O1—C1—O2 | 127.0 (3) | C20—C21—C22 | 120.3 (4) |
O1—C1—C2 | 117.1 (3) | C20—C21—H21A | 119.9 |
O2—C1—C2 | 115.9 (3) | C22—C21—H21A | 119.9 |
C16—C2—C3 | 119.7 (3) | C23—C22—C21 | 120.6 (3) |
C16—C2—C1 | 119.6 (3) | C23—C22—H22A | 119.7 |
C3—C2—C1 | 120.6 (3) | C21—C22—H22A | 119.7 |
C4—C3—C2 | 124.8 (3) | C22—C23—C24 | 120.7 (3) |
C4—C3—C8 | 118.4 (3) | C22—C23—H23A | 119.7 |
C2—C3—C8 | 116.7 (3) | C24—C23—H23A | 119.7 |
C5—C4—C3 | 121.1 (3) | N2—C24—C23 | 117.6 (3) |
C5—C4—H4A | 119.5 | N2—C24—C19 | 123.3 (3) |
C3—C4—H4A | 119.5 | C23—C24—C19 | 119.1 (3) |
C4—C5—C6 | 120.0 (3) | N2—C25—C32 | 122.5 (3) |
C4—C5—H5A | 120.0 | N2—C25—C26 | 116.8 (3) |
C6—C5—H5A | 120.0 | C32—C25—C26 | 120.6 (3) |
C7—C6—C5 | 121.0 (3) | C27—C26—C31 | 118.7 (4) |
C7—C6—H6A | 119.5 | C27—C26—C25 | 119.5 (3) |
C5—C6—H6A | 119.5 | C31—C26—C25 | 121.7 (3) |
C6—C7—C8 | 120.2 (3) | C26—C27—C28 | 120.7 (4) |
C6—C7—H7A | 119.9 | C26—C27—H27A | 119.7 |
C8—C7—H7A | 119.9 | C28—C27—H27A | 119.7 |
N1—C8—C7 | 118.5 (2) | C29—C28—C27 | 119.9 (4) |
N1—C8—C3 | 122.2 (3) | C29—C28—H28A | 120.1 |
C7—C8—C3 | 119.3 (3) | C27—C28—H28A | 120.1 |
N1—C9—C16 | 120.9 (3) | C30—C29—C28 | 119.9 (4) |
N1—C9—C10 | 118.2 (2) | C30—C29—H29A | 120.1 |
C16—C9—C10 | 120.8 (3) | C28—C29—H29A | 120.1 |
C15—C10—C11 | 118.4 (3) | C29—C30—C31 | 120.5 (5) |
C15—C10—C9 | 121.6 (3) | C29—C30—H30A | 119.7 |
C11—C10—C9 | 120.0 (3) | C31—C30—H30A | 119.7 |
C12—C11—C10 | 120.2 (4) | C26—C31—C30 | 120.3 (4) |
C12—C11—H11A | 119.9 | C26—C31—H31A | 119.9 |
C10—C11—H11A | 119.9 | C30—C31—H31A | 119.9 |
C13—C12—C11 | 120.2 (4) | C18—C32—C25 | 120.4 (3) |
C13—C12—H12A | 119.9 | C18—C32—H32A | 119.8 |
C11—C12—H12A | 119.9 | C25—C32—H32A | 119.8 |
C14—C13—C12 | 120.1 (4) | C1—O1—Cu1 | 116.8 (2) |
C14—C13—H13A | 120.0 | C1—O2—Cu1i | 128.4 (2) |
C12—C13—H13A | 120.0 | C17—O3—Cu1 | 120.9 (2) |
C13—C14—C15 | 120.0 (4) | C17—O4—Cu1i | 124.7 (2) |
C13—C14—H14A | 120.0 | Cu1—O1W—H1 | 144.7 |
C15—C14—H14A | 120.0 | Cu1—O1W—H2 | 112.2 |
C14—C15—C10 | 121.1 (3) | H1—O1W—H2 | 102.8 |
| | | |
O1—C1—C2—C16 | −57.9 (4) | C24—C19—C20—C21 | −2.0 (5) |
O2—C1—C2—C16 | 121.3 (3) | C19—C20—C21—C22 | 1.1 (6) |
O1—C1—C2—C3 | 123.7 (3) | C20—C21—C22—C23 | 0.2 (6) |
O2—C1—C2—C3 | −57.1 (4) | C21—C22—C23—C24 | −0.6 (6) |
C16—C2—C3—C4 | 179.5 (3) | C25—N2—C24—C23 | 179.1 (3) |
C1—C2—C3—C4 | −2.2 (5) | C25—N2—C24—C19 | 0.0 (5) |
C16—C2—C3—C8 | 0.9 (4) | C22—C23—C24—N2 | −179.5 (4) |
C1—C2—C3—C8 | 179.2 (3) | C22—C23—C24—C19 | −0.4 (5) |
C2—C3—C4—C5 | −177.9 (3) | C20—C19—C24—N2 | −179.3 (3) |
C8—C3—C4—C5 | 0.6 (5) | C18—C19—C24—N2 | 1.5 (5) |
C3—C4—C5—C6 | 1.1 (6) | C20—C19—C24—C23 | 1.6 (5) |
C4—C5—C6—C7 | −2.0 (6) | C18—C19—C24—C23 | −177.6 (3) |
C5—C6—C7—C8 | 1.1 (5) | C24—N2—C25—C32 | −1.9 (5) |
C9—N1—C8—C7 | −178.3 (3) | C24—N2—C25—C26 | −179.1 (3) |
C9—N1—C8—C3 | 2.6 (4) | N2—C25—C26—C27 | 35.3 (5) |
C6—C7—C8—N1 | −178.5 (3) | C32—C25—C26—C27 | −141.9 (4) |
C6—C7—C8—C3 | 0.5 (5) | N2—C25—C26—C31 | −144.9 (4) |
C4—C3—C8—N1 | 177.6 (3) | C32—C25—C26—C31 | 37.8 (5) |
C2—C3—C8—N1 | −3.7 (4) | C31—C26—C27—C28 | −2.0 (6) |
C4—C3—C8—C7 | −1.4 (4) | C25—C26—C27—C28 | 177.8 (4) |
C2—C3—C8—C7 | 177.2 (3) | C26—C27—C28—C29 | 2.7 (7) |
C8—N1—C9—C16 | 1.3 (4) | C27—C28—C29—C30 | −1.7 (8) |
C8—N1—C9—C10 | −176.8 (3) | C28—C29—C30—C31 | 0.1 (8) |
N1—C9—C10—C15 | −142.3 (3) | C27—C26—C31—C30 | 0.4 (7) |
C16—C9—C10—C15 | 39.7 (5) | C25—C26—C31—C30 | −179.4 (4) |
N1—C9—C10—C11 | 38.6 (4) | C29—C30—C31—C26 | 0.6 (8) |
C16—C9—C10—C11 | −139.5 (3) | C19—C18—C32—C25 | −0.8 (5) |
C15—C10—C11—C12 | −0.2 (5) | C17—C18—C32—C25 | −179.6 (3) |
C9—C10—C11—C12 | 179.0 (3) | N2—C25—C32—C18 | 2.4 (5) |
C10—C11—C12—C13 | 1.2 (6) | C26—C25—C32—C18 | 179.5 (3) |
C11—C12—C13—C14 | −0.8 (7) | O2—C1—O1—Cu1 | 0.2 (4) |
C12—C13—C14—C15 | −0.7 (7) | C2—C1—O1—Cu1 | 179.34 (19) |
C13—C14—C15—C10 | 1.8 (6) | O3—Cu1—O1—C1 | −87.7 (2) |
C11—C10—C15—C14 | −1.3 (6) | O4i—Cu1—O1—C1 | 80.1 (2) |
C9—C10—C15—C14 | 179.5 (3) | O2i—Cu1—O1—C1 | −12.1 (6) |
C3—C2—C16—C9 | 2.8 (5) | O1W—Cu1—O1—C1 | 172.8 (2) |
C1—C2—C16—C9 | −175.5 (3) | Cu1i—Cu1—O1—C1 | −2.0 (2) |
N1—C9—C16—C2 | −4.1 (5) | O1—C1—O2—Cu1i | 3.0 (5) |
C10—C9—C16—C2 | 173.9 (3) | C2—C1—O2—Cu1i | −176.08 (18) |
O4—C17—C18—C32 | −123.5 (3) | O4—C17—O3—Cu1 | 0.2 (4) |
O3—C17—C18—C32 | 54.3 (4) | C18—C17—O3—Cu1 | −177.35 (18) |
O4—C17—C18—C19 | 57.8 (4) | O1—Cu1—O3—C17 | 90.5 (2) |
O3—C17—C18—C19 | −124.4 (3) | O4i—Cu1—O3—C17 | 8.7 (6) |
C32—C18—C19—C20 | 179.8 (3) | O2i—Cu1—O3—C17 | −77.4 (2) |
C17—C18—C19—C20 | −1.5 (5) | O1W—Cu1—O3—C17 | −170.4 (2) |
C32—C18—C19—C24 | −1.0 (4) | Cu1i—Cu1—O3—C17 | 1.3 (2) |
C17—C18—C19—C24 | 177.7 (3) | O3—C17—O4—Cu1i | −2.4 (4) |
C18—C19—C20—C21 | 177.1 (4) | C18—C17—O4—Cu1i | 175.08 (18) |
Symmetry code: (i) −x+1, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H2···N1ii | 0.84 | 2.05 | 2.873 (3) | 169 |
Symmetry code: (ii) x, y+1, z. |