One naphthalene-1,4-dicarboxylate dianion in the title compound, [Cu2(C12H6O4)2(C14H8N4)2]·4H2O, bridges two N-heterocycle-chelated Cu atoms whereas the other one bridges four N-heterocycle-chelated Cu atoms, linking them into a flat carboxylate-bridged layer. The two independent Cu atoms show square-pyramidal coordination. Water molecules occupy the space between adjacent layers; they are possibly disordered, and their H atoms were not located.
Supporting information
CCDC reference: 672638
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.007 Å
- H-atom completeness 78%
- R factor = 0.055
- wR factor = 0.190
- Data-to-parameter ratio = 15.8
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT220_ALERT_2_A Large Non-Solvent O Ueq(max)/Ueq(min) ... 4.65 Ratio
| Author Response: The lattice water molecules are disordered, but the disorder was not
treated.
|
PLAT306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O1W
| Author Response: Hydrogen atoms for the four water molecules are not placed.
|
PLAT306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O2W
| Author Response: Hydrogen atoms for the four water molecules are not placed.
|
PLAT306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O3W
| Author Response: Hydrogen atoms for the four water molecules are not placed.
|
PLAT306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O4W
| Author Response: Hydrogen atoms for the four water molecules are not placed.
|
Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact O1W .. O2 .. 2.80 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact O3W .. O4W .. 2.61 Ang.
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.88
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.04
PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 2346.00 Ang-3
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 2000 Deg.
PLAT213_ALERT_2_C Atom O6 has ADP max/min Ratio ............. 3.30 prola
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.68 Ratio
| Author Response: The lattice water molecules are disordered, but the disorder was not
treated.
|
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7
PLAT430_ALERT_2_C Short Inter D...A Contact O4 .. O4W .. 2.86 Ang.
Alert level G
FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and the formula from the _atom_site* data.
Atom count from _chemical_formula_sum:C52 H36 Cu2 N8 O12
Atom count from the _atom_site data: C52 H28 Cu2 N8 O12
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
From the CIF: _cell_formula_units_Z 2
From the CIF: _chemical_formula_sum C52 H36 Cu2 N8 O12
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 104.00 104.00 0.00
H 72.00 56.00 16.00
Cu 4.00 4.00 0.00
N 16.00 16.00 0.00
O 24.00 24.00 0.00
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1 (2) 2.06
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu2 (2) 2.12
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 436
5 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
13 ALERT level C = Check and explain
6 ALERT level G = General alerts; check
8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
13 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
2 ALERT type 5 Informative message, check
Copper chloride dihydrate (0.1 mmol), naphthalene-1,4-dicarboxylic acid (0.1 mmol), pyrazino[2,3-f][1,10]phenanthroline and water (12 ml) were
sealed in a 23-ml Teflon-lined Parr bomb, which was heated at 423 K for two
days. Blue block crystals were picked from the cool solution by hand in about
30% yield.
As all C–, N– and O-atoms showed somewhat elongated ellipsoids, their
anisotropic temperature factors were restrained to be nearly isotropic. The
O2, O4, O6 and O8 atoms, which are not involved in coordination, showed large
displacement parameters. An attempt was made to refine each atom as two atoms
of half site-occupancy each, with the pairs of C–O double-bond distances
restrained to within 0.01 Å of each other. However, this treatment required
the carboxyl –CO2 group to be approximately planar, so that the O1, O3, O5
and O7 atoms that are involved in coordination would have to be split into
two. As the treatment led to only a minor separation between the disorder
components, the structure was refined without disorder.
Carbon-bound H atoms were placed in calculated positions [C—H 0.93–0.97 Å
and Uiso(H) 1.2–1.5Ueq(C)], and were included in the
refinement in the riding-model approximation. The water H-atoms could not be
placed in chemically sensible positions on the basis of hydrogen bonding, and
were not included.
The final difference Fourier map had a large peak near O3w.
Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO (Rigaku Corporation, 1998); 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: X-SEED (Barbour, 2001); OLEX (Dolomanov et al., 2003); software used to prepare material for publication: publCIF (Westrip, 2007).
Poly[[(µ
4-naphthalene-1,4-dicarboxylato-
κ4O:
O:
O:
O')(µ
2-naphthalene-1,4-
dicarboxylato-
κ2O:
O')bis(pyrazino[2,3-
f][1,10]phenanthroline-
κ2N,
N')dicopper(II)] tetrahydrate]
top
Crystal data top
[Cu2(C12H6O4)2(C14H8N4)2]·4H2O | Z = 2 |
Mr = 1091.97 | F(000) = 1116 |
Triclinic, P1 | Dx = 1.546 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 12.679 (5) Å | Cell parameters from 15645 reflections |
b = 14.690 (6) Å | θ = 3.0–27.5° |
c = 14.833 (7) Å | µ = 0.98 mm−1 |
α = 69.37 (2)° | T = 295 K |
β = 82.05 (2)° | Block, blue |
γ = 65.13 (2)° | 0.38 × 0.27 × 0.16 mm |
V = 2346 (2) Å3 | |
Data collection top
Rigaku RAXIS-RAPID diffractometer | 10535 independent reflections |
Radiation source: fine-focus sealed tube | 6887 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
Detector resolution: 10.000 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
ω–scans | h = −16→16 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −18→19 |
Tmin = 0.618, Tmax = 0.859 | l = −19→19 |
22789 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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.190 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.1132P)2] where P = (Fo2 + 2Fc2)/3 |
10535 reflections | (Δ/σ)max = 0.001 |
667 parameters | Δρmax = 1.03 e Å−3 |
436 restraints | Δρmin = −0.51 e Å−3 |
Crystal data top
[Cu2(C12H6O4)2(C14H8N4)2]·4H2O | γ = 65.13 (2)° |
Mr = 1091.97 | V = 2346 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 12.679 (5) Å | Mo Kα radiation |
b = 14.690 (6) Å | µ = 0.98 mm−1 |
c = 14.833 (7) Å | T = 295 K |
α = 69.37 (2)° | 0.38 × 0.27 × 0.16 mm |
β = 82.05 (2)° | |
Data collection top
Rigaku RAXIS-RAPID diffractometer | 10535 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 6887 reflections with I > 2σ(I) |
Tmin = 0.618, Tmax = 0.859 | Rint = 0.032 |
22789 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.055 | 436 restraints |
wR(F2) = 0.190 | H-atom parameters constrained |
S = 1.09 | Δρmax = 1.03 e Å−3 |
10535 reflections | Δρmin = −0.51 e Å−3 |
667 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.40502 (3) | 0.45832 (4) | 0.46309 (3) | 0.03280 (15) | |
Cu2 | 1.08859 (3) | 0.04876 (3) | 0.02766 (3) | 0.03177 (15) | |
O1 | 0.5140 (2) | 0.4239 (2) | 0.3639 (2) | 0.0448 (7) | |
O2 | 0.4999 (3) | 0.2724 (3) | 0.3878 (3) | 0.0798 (12) | |
O3 | 0.9640 (2) | 0.1145 (3) | 0.1032 (2) | 0.0484 (7) | |
O4 | 0.9801 (3) | 0.2685 (3) | 0.0434 (3) | 0.0950 (14) | |
O5 | 0.5321 (2) | 0.4001 (2) | 0.55622 (19) | 0.0403 (6) | |
O6 | 0.5128 (5) | 0.2520 (4) | 0.6161 (4) | 0.166 (3) | |
O7 | 0.9755 (2) | 0.0895 (2) | 0.92765 (18) | 0.0358 (6) | |
O8 | 1.0457 (3) | 0.1950 (3) | 0.8171 (3) | 0.0884 (14) | |
O1W | 0.4320 (7) | 0.1517 (6) | 0.3165 (6) | 0.172 (3) | |
O2W | 0.4226 (10) | −0.0548 (8) | 0.4733 (8) | 0.264 (5) | |
O3W | 0.2273 (10) | 0.2971 (9) | 0.1769 (10) | 0.269 (5) | |
O4W | 0.0234 (8) | 0.4201 (7) | 0.0950 (7) | 0.199 (3) | |
N1 | 0.2756 (3) | 0.5119 (3) | 0.5508 (2) | 0.0365 (7) | |
N2 | −0.1416 (3) | 0.6969 (3) | 0.5521 (3) | 0.0618 (11) | |
N3 | −0.1518 (3) | 0.6744 (3) | 0.3731 (3) | 0.0564 (11) | |
N4 | 0.2664 (3) | 0.5018 (3) | 0.3791 (2) | 0.0374 (7) | |
N5 | 1.2335 (3) | −0.0271 (3) | −0.0366 (2) | 0.0370 (7) | |
N6 | 1.6504 (3) | −0.2026 (4) | 0.0081 (4) | 0.0778 (15) | |
N7 | 1.6236 (4) | −0.1483 (4) | 0.1776 (4) | 0.0813 (16) | |
N8 | 1.2092 (3) | 0.0200 (3) | 0.1218 (2) | 0.0419 (8) | |
C1 | 0.5436 (3) | 0.3354 (4) | 0.3488 (3) | 0.0456 (10) | |
C2 | 0.6396 (4) | 0.3128 (3) | 0.2770 (3) | 0.0410 (9) | |
C3 | 0.6428 (3) | 0.3867 (3) | 0.1860 (3) | 0.0412 (9) | |
C4 | 0.5545 (4) | 0.4905 (4) | 0.1521 (3) | 0.0542 (11) | |
H4 | 0.4929 | 0.5122 | 0.1924 | 0.065* | |
C5 | 0.5566 (5) | 0.5586 (5) | 0.0639 (4) | 0.0773 (17) | |
H5 | 0.4963 | 0.6256 | 0.0439 | 0.093* | |
C6 | 0.6494 (5) | 0.5291 (5) | 0.0019 (4) | 0.0838 (18) | |
H6 | 0.6509 | 0.5767 | −0.0589 | 0.101* | |
C7 | 0.7375 (5) | 0.4303 (5) | 0.0309 (4) | 0.0701 (15) | |
H7 | 0.7980 | 0.4115 | −0.0111 | 0.084* | |
C8 | 0.7392 (4) | 0.3555 (4) | 0.1236 (3) | 0.0448 (10) | |
C9 | 0.8284 (4) | 0.2514 (4) | 0.1551 (3) | 0.0446 (10) | |
C10 | 0.8216 (4) | 0.1838 (4) | 0.2438 (3) | 0.0497 (11) | |
H10 | 0.8805 | 0.1161 | 0.2646 | 0.060* | |
C11 | 0.7283 (4) | 0.2133 (4) | 0.3046 (3) | 0.0475 (10) | |
H11 | 0.7261 | 0.1648 | 0.3647 | 0.057* | |
C12 | 0.9324 (3) | 0.2109 (4) | 0.0949 (3) | 0.0519 (11) | |
C13 | 0.5642 (3) | 0.3075 (4) | 0.6105 (3) | 0.0597 (14) | |
C14 | 0.6719 (4) | 0.2660 (3) | 0.6709 (3) | 0.0467 (11) | |
C15 | 0.7829 (4) | 0.2141 (4) | 0.6364 (3) | 0.0525 (12) | |
C16 | 0.7986 (5) | 0.1958 (5) | 0.5469 (4) | 0.0658 (14) | |
H16 | 0.7337 | 0.2181 | 0.5094 | 0.079* | |
C17 | 0.9053 (6) | 0.1467 (5) | 0.5149 (4) | 0.0778 (17) | |
H17 | 0.9133 | 0.1356 | 0.4559 | 0.093* | |
C18 | 1.0043 (5) | 0.1124 (5) | 0.5705 (5) | 0.0752 (16) | |
H18 | 1.0777 | 0.0779 | 0.5485 | 0.090* | |
C19 | 0.9937 (4) | 0.1291 (4) | 0.6554 (4) | 0.0594 (13) | |
H19 | 1.0604 | 0.1067 | 0.6907 | 0.071* | |
C20 | 0.8835 (4) | 0.1799 (3) | 0.6927 (3) | 0.0458 (10) | |
C21 | 0.8679 (3) | 0.1958 (3) | 0.7835 (3) | 0.0451 (11) | |
C22 | 0.7598 (4) | 0.2426 (4) | 0.8150 (3) | 0.0497 (11) | |
H22 | 0.7507 | 0.2500 | 0.8756 | 0.060* | |
C23 | 0.6608 (4) | 0.2801 (4) | 0.7583 (4) | 0.0533 (12) | |
H23 | 0.5875 | 0.3146 | 0.7804 | 0.064* | |
C24 | 0.9719 (3) | 0.1584 (3) | 0.8466 (3) | 0.0448 (10) | |
C25 | 0.2843 (4) | 0.5114 (4) | 0.6399 (3) | 0.0494 (11) | |
H25 | 0.3574 | 0.4808 | 0.6686 | 0.059* | |
C26 | 0.1866 (4) | 0.5557 (4) | 0.6905 (3) | 0.0559 (12) | |
H26 | 0.1953 | 0.5534 | 0.7526 | 0.067* | |
C27 | 0.0786 (4) | 0.6022 (4) | 0.6508 (4) | 0.0523 (11) | |
H27 | 0.0135 | 0.6327 | 0.6846 | 0.063* | |
C28 | 0.0674 (3) | 0.6034 (3) | 0.5569 (3) | 0.0418 (9) | |
C29 | 0.1678 (3) | 0.5570 (3) | 0.5106 (3) | 0.0341 (8) | |
C30 | −0.0446 (3) | 0.6484 (3) | 0.5075 (3) | 0.0437 (10) | |
C31 | −0.2407 (4) | 0.7337 (4) | 0.5027 (5) | 0.0748 (17) | |
H31 | −0.3103 | 0.7697 | 0.5288 | 0.090* | |
C32 | −0.2450 (4) | 0.7213 (4) | 0.4169 (5) | 0.0688 (16) | |
H32 | −0.3171 | 0.7471 | 0.3881 | 0.083* | |
C33 | −0.0489 (3) | 0.6382 (3) | 0.4184 (3) | 0.0431 (10) | |
C34 | 0.0568 (3) | 0.5868 (3) | 0.3719 (3) | 0.0372 (9) | |
C35 | 0.1630 (3) | 0.5495 (3) | 0.4170 (3) | 0.0344 (8) | |
C36 | 0.0581 (4) | 0.5722 (4) | 0.2839 (3) | 0.0485 (11) | |
H36 | −0.0110 | 0.5966 | 0.2510 | 0.058* | |
C37 | 0.1624 (4) | 0.5215 (4) | 0.2462 (3) | 0.0545 (12) | |
H37 | 0.1647 | 0.5098 | 0.1882 | 0.065* | |
C38 | 0.2649 (4) | 0.4877 (4) | 0.2954 (3) | 0.0461 (10) | |
H38 | 0.3352 | 0.4539 | 0.2688 | 0.055* | |
C39 | 1.2428 (4) | −0.0517 (4) | −0.1160 (3) | 0.0507 (11) | |
H39 | 1.1752 | −0.0320 | −0.1490 | 0.061* | |
C40 | 1.3496 (4) | −0.1059 (5) | −0.1521 (4) | 0.0703 (16) | |
H40 | 1.3522 | −0.1187 | −0.2097 | 0.084* | |
C41 | 1.4494 (4) | −0.1399 (4) | −0.1038 (4) | 0.0653 (14) | |
H41 | 1.5206 | −0.1774 | −0.1268 | 0.078* | |
C42 | 1.4433 (3) | −0.1176 (4) | −0.0183 (4) | 0.0500 (11) | |
C43 | 1.3335 (3) | −0.0605 (3) | 0.0128 (3) | 0.0413 (9) | |
C44 | 1.5449 (4) | −0.1491 (4) | 0.0385 (4) | 0.0564 (13) | |
C45 | 1.7391 (5) | −0.2288 (5) | 0.0639 (6) | 0.092 (2) | |
H45 | 1.8138 | −0.2663 | 0.0461 | 0.110* | |
C46 | 1.7261 (5) | −0.2040 (5) | 0.1441 (5) | 0.083 (2) | |
H46 | 1.7928 | −0.2268 | 0.1797 | 0.100* | |
C47 | 1.5308 (4) | −0.1213 (4) | 0.1220 (4) | 0.0596 (14) | |
C48 | 1.4168 (4) | −0.0613 (4) | 0.1527 (3) | 0.0505 (12) | |
C49 | 1.3201 (3) | −0.0329 (3) | 0.0982 (3) | 0.0400 (9) | |
C50 | 1.3978 (5) | −0.0324 (4) | 0.2340 (4) | 0.0670 (16) | |
H50 | 1.4603 | −0.0486 | 0.2715 | 0.080* | |
C51 | 1.2862 (5) | 0.0203 (5) | 0.2597 (4) | 0.0687 (15) | |
H51 | 1.2724 | 0.0392 | 0.3152 | 0.082* | |
C52 | 1.1935 (4) | 0.0454 (4) | 0.2016 (3) | 0.0564 (12) | |
H52 | 1.1181 | 0.0811 | 0.2195 | 0.068* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0200 (2) | 0.0465 (3) | 0.0297 (2) | −0.00772 (19) | −0.00046 (17) | −0.0166 (2) |
Cu2 | 0.0223 (2) | 0.0404 (3) | 0.0325 (3) | −0.00717 (19) | −0.00198 (18) | −0.0176 (2) |
O1 | 0.0337 (14) | 0.064 (2) | 0.0453 (16) | −0.0163 (13) | 0.0082 (12) | −0.0347 (15) |
O2 | 0.083 (3) | 0.069 (3) | 0.095 (3) | −0.041 (2) | 0.049 (2) | −0.039 (2) |
O3 | 0.0386 (15) | 0.059 (2) | 0.0553 (18) | −0.0118 (14) | 0.0079 (13) | −0.0397 (15) |
O4 | 0.080 (3) | 0.075 (3) | 0.131 (4) | −0.035 (2) | 0.065 (3) | −0.053 (3) |
O5 | 0.0303 (13) | 0.0463 (17) | 0.0372 (14) | −0.0089 (12) | −0.0103 (11) | −0.0097 (12) |
O6 | 0.147 (4) | 0.117 (4) | 0.211 (5) | −0.098 (4) | −0.135 (4) | 0.081 (4) |
O7 | 0.0293 (13) | 0.0411 (15) | 0.0345 (13) | −0.0118 (11) | −0.0063 (11) | −0.0097 (11) |
O8 | 0.066 (2) | 0.099 (3) | 0.084 (3) | −0.057 (2) | −0.035 (2) | 0.032 (2) |
O1W | 0.197 (6) | 0.211 (6) | 0.183 (6) | −0.103 (5) | 0.048 (5) | −0.141 (5) |
O2W | 0.328 (9) | 0.227 (8) | 0.238 (8) | −0.108 (7) | −0.058 (7) | −0.058 (7) |
O3W | 0.299 (9) | 0.204 (7) | 0.322 (10) | −0.126 (7) | 0.007 (7) | −0.078 (7) |
O4W | 0.228 (7) | 0.191 (7) | 0.233 (7) | −0.109 (6) | −0.009 (6) | −0.096 (5) |
N1 | 0.0255 (15) | 0.052 (2) | 0.0351 (16) | −0.0147 (14) | 0.0023 (13) | −0.0198 (15) |
N2 | 0.0331 (19) | 0.062 (3) | 0.081 (3) | −0.0132 (17) | 0.0146 (19) | −0.025 (2) |
N3 | 0.0281 (18) | 0.054 (2) | 0.075 (3) | −0.0136 (16) | −0.0103 (18) | −0.006 (2) |
N4 | 0.0279 (16) | 0.049 (2) | 0.0358 (16) | −0.0146 (14) | −0.0005 (13) | −0.0153 (15) |
N5 | 0.0241 (15) | 0.0434 (19) | 0.0405 (17) | −0.0082 (13) | −0.0024 (13) | −0.0160 (14) |
N6 | 0.0276 (19) | 0.069 (3) | 0.107 (4) | −0.0112 (19) | −0.006 (2) | −0.002 (3) |
N7 | 0.049 (2) | 0.093 (3) | 0.081 (3) | −0.039 (2) | −0.029 (2) | 0.019 (3) |
N8 | 0.0455 (19) | 0.047 (2) | 0.0385 (17) | −0.0212 (16) | −0.0095 (15) | −0.0123 (15) |
C1 | 0.037 (2) | 0.060 (3) | 0.042 (2) | −0.017 (2) | 0.0058 (18) | −0.024 (2) |
C2 | 0.039 (2) | 0.050 (2) | 0.041 (2) | −0.0161 (18) | 0.0030 (17) | −0.0263 (18) |
C3 | 0.038 (2) | 0.048 (2) | 0.039 (2) | −0.0114 (17) | 0.0058 (17) | −0.0254 (18) |
C4 | 0.043 (2) | 0.051 (3) | 0.055 (3) | −0.008 (2) | 0.010 (2) | −0.019 (2) |
C5 | 0.075 (4) | 0.055 (3) | 0.067 (3) | −0.004 (3) | 0.005 (3) | −0.010 (3) |
C6 | 0.087 (4) | 0.073 (4) | 0.059 (3) | −0.021 (3) | 0.015 (3) | −0.006 (3) |
C7 | 0.072 (3) | 0.075 (4) | 0.051 (3) | −0.024 (3) | 0.020 (2) | −0.022 (3) |
C8 | 0.043 (2) | 0.053 (3) | 0.043 (2) | −0.0166 (19) | 0.0082 (18) | −0.0264 (19) |
C9 | 0.039 (2) | 0.051 (3) | 0.049 (2) | −0.0126 (18) | 0.0089 (18) | −0.032 (2) |
C10 | 0.050 (2) | 0.043 (2) | 0.051 (2) | −0.0058 (19) | 0.006 (2) | −0.027 (2) |
C11 | 0.050 (2) | 0.052 (3) | 0.038 (2) | −0.013 (2) | 0.0053 (18) | −0.0219 (19) |
C12 | 0.042 (2) | 0.059 (3) | 0.056 (3) | −0.016 (2) | 0.015 (2) | −0.031 (2) |
C13 | 0.045 (2) | 0.055 (3) | 0.069 (3) | −0.026 (2) | −0.033 (2) | 0.012 (2) |
C14 | 0.038 (2) | 0.038 (2) | 0.052 (2) | −0.0141 (18) | −0.0200 (19) | 0.0060 (18) |
C15 | 0.051 (3) | 0.054 (3) | 0.048 (2) | −0.030 (2) | −0.019 (2) | 0.005 (2) |
C16 | 0.064 (3) | 0.084 (4) | 0.053 (3) | −0.034 (3) | −0.012 (2) | −0.016 (3) |
C17 | 0.090 (4) | 0.088 (4) | 0.062 (3) | −0.041 (3) | −0.007 (3) | −0.022 (3) |
C18 | 0.067 (3) | 0.072 (4) | 0.080 (4) | −0.023 (3) | 0.007 (3) | −0.027 (3) |
C19 | 0.052 (3) | 0.057 (3) | 0.062 (3) | −0.023 (2) | −0.011 (2) | −0.005 (2) |
C20 | 0.038 (2) | 0.045 (2) | 0.047 (2) | −0.0190 (18) | −0.0133 (19) | 0.0008 (18) |
C21 | 0.032 (2) | 0.042 (2) | 0.049 (2) | −0.0174 (17) | −0.0159 (18) | 0.0078 (18) |
C22 | 0.040 (2) | 0.053 (3) | 0.050 (2) | −0.0193 (19) | −0.0116 (19) | −0.004 (2) |
C23 | 0.033 (2) | 0.047 (3) | 0.068 (3) | −0.0118 (18) | −0.015 (2) | −0.005 (2) |
C24 | 0.031 (2) | 0.048 (2) | 0.045 (2) | −0.0144 (18) | −0.0130 (18) | −0.0004 (18) |
C25 | 0.033 (2) | 0.083 (3) | 0.043 (2) | −0.026 (2) | 0.0028 (17) | −0.030 (2) |
C26 | 0.048 (3) | 0.093 (4) | 0.048 (2) | −0.034 (2) | 0.011 (2) | −0.043 (2) |
C27 | 0.042 (2) | 0.067 (3) | 0.064 (3) | −0.026 (2) | 0.021 (2) | −0.041 (2) |
C28 | 0.0299 (19) | 0.047 (2) | 0.051 (2) | −0.0175 (17) | 0.0084 (17) | −0.0198 (19) |
C29 | 0.0256 (17) | 0.041 (2) | 0.0377 (19) | −0.0150 (15) | 0.0030 (15) | −0.0147 (16) |
C30 | 0.0262 (18) | 0.039 (2) | 0.061 (3) | −0.0124 (16) | 0.0056 (18) | −0.0135 (19) |
C31 | 0.021 (2) | 0.073 (4) | 0.104 (4) | −0.005 (2) | 0.008 (3) | −0.019 (3) |
C32 | 0.030 (2) | 0.064 (3) | 0.093 (4) | −0.014 (2) | −0.011 (3) | −0.006 (3) |
C33 | 0.0269 (19) | 0.038 (2) | 0.057 (2) | −0.0139 (16) | −0.0053 (18) | −0.0034 (18) |
C34 | 0.0268 (18) | 0.040 (2) | 0.0400 (19) | −0.0135 (16) | −0.0072 (16) | −0.0044 (16) |
C35 | 0.0279 (18) | 0.037 (2) | 0.0366 (19) | −0.0146 (15) | 0.0003 (15) | −0.0075 (16) |
C36 | 0.044 (2) | 0.059 (3) | 0.042 (2) | −0.026 (2) | −0.0122 (19) | −0.0059 (19) |
C37 | 0.057 (3) | 0.077 (3) | 0.036 (2) | −0.031 (2) | −0.007 (2) | −0.017 (2) |
C38 | 0.036 (2) | 0.070 (3) | 0.035 (2) | −0.021 (2) | 0.0015 (17) | −0.0209 (19) |
C39 | 0.035 (2) | 0.068 (3) | 0.058 (3) | −0.017 (2) | 0.0049 (19) | −0.036 (2) |
C40 | 0.042 (3) | 0.099 (4) | 0.085 (4) | −0.024 (3) | 0.018 (3) | −0.060 (3) |
C41 | 0.034 (2) | 0.068 (3) | 0.095 (4) | −0.012 (2) | 0.016 (2) | −0.045 (3) |
C42 | 0.0228 (19) | 0.046 (2) | 0.071 (3) | −0.0091 (17) | −0.0041 (19) | −0.012 (2) |
C43 | 0.0266 (18) | 0.040 (2) | 0.052 (2) | −0.0137 (16) | −0.0056 (17) | −0.0069 (18) |
C44 | 0.029 (2) | 0.044 (3) | 0.078 (3) | −0.0104 (18) | −0.012 (2) | 0.000 (2) |
C45 | 0.033 (3) | 0.083 (4) | 0.117 (5) | −0.015 (3) | −0.013 (3) | 0.009 (4) |
C46 | 0.037 (3) | 0.088 (4) | 0.107 (5) | −0.028 (3) | −0.031 (3) | 0.005 (3) |
C47 | 0.033 (2) | 0.053 (3) | 0.077 (3) | −0.023 (2) | −0.027 (2) | 0.013 (2) |
C48 | 0.048 (2) | 0.048 (3) | 0.052 (2) | −0.025 (2) | −0.021 (2) | 0.002 (2) |
C49 | 0.035 (2) | 0.038 (2) | 0.045 (2) | −0.0155 (17) | −0.0133 (18) | −0.0042 (17) |
C50 | 0.071 (3) | 0.071 (3) | 0.067 (3) | −0.040 (3) | −0.029 (3) | −0.006 (3) |
C51 | 0.087 (4) | 0.085 (4) | 0.049 (3) | −0.039 (3) | −0.015 (3) | −0.028 (3) |
C52 | 0.061 (3) | 0.067 (3) | 0.050 (2) | −0.026 (2) | −0.006 (2) | −0.025 (2) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.924 (3) | C15—C16 | 1.416 (7) |
Cu1—O5 | 1.965 (2) | C15—C20 | 1.427 (5) |
Cu1—O5i | 2.440 (3) | C16—C17 | 1.349 (8) |
Cu1—N1 | 2.012 (3) | C16—H16 | 0.9300 |
Cu1—N4 | 2.037 (3) | C17—C18 | 1.404 (8) |
Cu2—O3 | 1.916 (3) | C17—H17 | 0.9300 |
Cu2—O7ii | 1.964 (2) | C18—C19 | 1.345 (8) |
Cu2—O7iii | 2.348 (3) | C18—H18 | 0.9300 |
Cu2—N5 | 2.017 (3) | C19—C20 | 1.419 (7) |
Cu2—N8 | 2.024 (3) | C19—H19 | 0.9300 |
O1—C1 | 1.287 (5) | C20—C21 | 1.421 (6) |
O2—C1 | 1.209 (5) | C21—C22 | 1.352 (6) |
O3—C12 | 1.262 (6) | C21—C24 | 1.511 (5) |
O4—C12 | 1.230 (6) | C22—C23 | 1.404 (6) |
O5—C13 | 1.232 (5) | C22—H22 | 0.9300 |
O5—Cu1i | 2.440 (3) | C23—H23 | 0.9300 |
O6—C13 | 1.216 (6) | C25—C26 | 1.390 (6) |
O7—C24 | 1.262 (5) | C25—H25 | 0.9300 |
O7—Cu2iv | 1.964 (2) | C26—C27 | 1.357 (6) |
O7—Cu2iii | 2.348 (3) | C26—H26 | 0.9300 |
O8—C24 | 1.224 (5) | C27—C28 | 1.414 (6) |
N1—C25 | 1.339 (5) | C27—H27 | 0.9300 |
N1—C29 | 1.360 (5) | C28—C29 | 1.384 (6) |
N2—C31 | 1.347 (6) | C28—C30 | 1.464 (6) |
N2—C30 | 1.353 (6) | C29—C35 | 1.441 (5) |
N3—C32 | 1.308 (7) | C30—C33 | 1.393 (6) |
N3—C33 | 1.357 (5) | C31—C32 | 1.359 (8) |
N4—C38 | 1.332 (5) | C31—H31 | 0.9300 |
N4—C35 | 1.352 (5) | C32—H32 | 0.9300 |
N5—C39 | 1.325 (5) | C33—C34 | 1.449 (6) |
N5—C43 | 1.367 (5) | C34—C36 | 1.393 (6) |
N6—C45 | 1.329 (7) | C34—C35 | 1.391 (5) |
N6—C44 | 1.344 (7) | C36—C37 | 1.370 (7) |
N7—C46 | 1.349 (9) | C36—H36 | 0.9300 |
N7—C47 | 1.366 (5) | C37—C38 | 1.389 (6) |
N8—C52 | 1.329 (6) | C37—H37 | 0.9300 |
N8—C49 | 1.357 (5) | C38—H38 | 0.9300 |
C1—C2 | 1.508 (6) | C39—C40 | 1.396 (6) |
C2—C11 | 1.376 (6) | C39—H39 | 0.9300 |
C2—C3 | 1.412 (6) | C40—C41 | 1.354 (7) |
C3—C4 | 1.418 (6) | C40—H40 | 0.9300 |
C3—C8 | 1.441 (6) | C41—C42 | 1.402 (7) |
C4—C5 | 1.342 (7) | C41—H41 | 0.9300 |
C4—H4 | 0.9300 | C42—C43 | 1.402 (6) |
C5—C6 | 1.404 (8) | C42—C44 | 1.451 (6) |
C5—H5 | 0.9300 | C43—C49 | 1.429 (6) |
C6—C7 | 1.367 (8) | C44—C47 | 1.403 (8) |
C6—H6 | 0.9300 | C45—C46 | 1.334 (10) |
C7—C8 | 1.422 (7) | C45—H45 | 0.9300 |
C7—H7 | 0.9300 | C46—H46 | 0.9300 |
C8—C9 | 1.423 (6) | C47—C48 | 1.450 (7) |
C9—C10 | 1.358 (7) | C48—C50 | 1.373 (7) |
C9—C12 | 1.511 (6) | C48—C49 | 1.391 (5) |
C10—C11 | 1.396 (6) | C50—C51 | 1.373 (8) |
C10—H10 | 0.9300 | C50—H50 | 0.9300 |
C11—H11 | 0.9300 | C51—C52 | 1.396 (6) |
C13—C14 | 1.515 (5) | C51—H51 | 0.9300 |
C14—C23 | 1.363 (7) | C52—H52 | 0.9300 |
C14—C15 | 1.412 (7) | | |
| | | |
O1—Cu1—O5 | 91.2 (1) | C20—C19—H19 | 119.1 |
O1—Cu1—N1 | 171.5 (1) | C21—C20—C19 | 123.7 (4) |
O5—Cu1—N1 | 96.2 (1) | C21—C20—C15 | 118.5 (4) |
O1—Cu1—N4 | 92.4 (1) | C19—C20—C15 | 117.7 (4) |
O5—Cu1—N4 | 171.8 (1) | C22—C21—C20 | 120.1 (4) |
N1—Cu1—N4 | 80.8 (1) | C22—C21—C24 | 119.6 (4) |
O1—Cu1—O5i | 86.7 (1) | C20—C21—C24 | 120.3 (3) |
O5—Cu1—O5i | 72.8 (1) | C21—C22—C23 | 121.6 (5) |
N1—Cu1—O5i | 91.5 (1) | C21—C22—H22 | 119.2 |
N4—Cu1—O5i | 114.8 (1) | C23—C22—H22 | 119.2 |
O7ii—Cu2—O3 | 89.5 (1) | C14—C23—C22 | 120.1 (4) |
O7ii—Cu2—N5 | 98.1 (1) | C14—C23—H23 | 120.0 |
O3—Cu2—N5 | 172.4 (1) | C22—C23—H23 | 120.0 |
O7ii—Cu2—N8 | 173.9 (1) | O8—C24—O7 | 124.7 (3) |
O3—Cu2—N8 | 91.7 (1) | O8—C24—C21 | 119.6 (4) |
N5—Cu2—N8 | 80.8 (1) | O7—C24—C21 | 115.7 (3) |
O7ii—Cu2—O7iii | 74.6 (1) | N1—C25—C26 | 121.4 (4) |
O3—Cu2—O7iii | 87.0 (1) | N1—C25—H25 | 119.3 |
N5—Cu2—O7iii | 94.3 (1) | C26—C25—H25 | 119.3 |
N8—Cu2—O7iii | 111.4 (1) | C27—C26—C25 | 121.1 (4) |
C1—O1—Cu1 | 120.8 (3) | C27—C26—H26 | 119.5 |
C12—O3—Cu2 | 120.9 (3) | C25—C26—H26 | 119.5 |
C13—O5—Cu1 | 120.1 (3) | C26—C27—C28 | 118.4 (4) |
C13—O5—Cu1i | 132.6 (2) | C26—C27—H27 | 120.8 |
Cu1—O5—Cu1i | 107.22 (12) | C28—C27—H27 | 120.8 |
C24—O7—Cu2iv | 121.6 (2) | C29—C28—C27 | 117.8 (4) |
C24—O7—Cu2iii | 129.8 (2) | C29—C28—C30 | 118.6 (4) |
Cu2iv—O7—Cu2iii | 105.40 (11) | C27—C28—C30 | 123.5 (4) |
C25—N1—C29 | 118.1 (3) | N1—C29—C28 | 123.1 (4) |
C25—N1—Cu1 | 128.0 (3) | N1—C29—C35 | 115.7 (3) |
C29—N1—Cu1 | 113.8 (2) | C28—C29—C35 | 121.1 (3) |
C31—N2—C30 | 114.0 (5) | N2—C30—C33 | 122.1 (4) |
C32—N3—C33 | 116.1 (5) | N2—C30—C28 | 118.0 (4) |
C38—N4—C35 | 117.6 (3) | C33—C30—C28 | 119.9 (4) |
C38—N4—Cu1 | 129.1 (3) | N2—C31—C32 | 123.8 (5) |
C35—N4—Cu1 | 113.3 (2) | N2—C31—H31 | 118.1 |
C39—N5—C43 | 117.6 (4) | C32—C31—H31 | 118.1 |
C39—N5—Cu2 | 128.9 (3) | N3—C32—C31 | 122.7 (5) |
C43—N5—Cu2 | 113.5 (3) | N3—C32—H32 | 118.7 |
C45—N6—C44 | 115.2 (6) | C31—C32—H32 | 118.7 |
C46—N7—C47 | 113.0 (6) | N3—C33—C30 | 121.2 (4) |
C52—N8—C49 | 117.4 (4) | N3—C33—C34 | 118.0 (4) |
C52—N8—Cu2 | 128.8 (3) | C30—C33—C34 | 120.8 (3) |
C49—N8—Cu2 | 113.8 (3) | C36—C34—C35 | 117.7 (4) |
O2—C1—O1 | 124.3 (4) | C36—C34—C33 | 123.5 (4) |
O2—C1—C2 | 120.3 (4) | C35—C34—C33 | 118.8 (4) |
O1—C1—C2 | 115.4 (4) | N4—C35—C34 | 123.4 (4) |
C11—C2—C3 | 119.7 (4) | N4—C35—C29 | 116.0 (3) |
C11—C2—C1 | 116.2 (4) | C34—C35—C29 | 120.6 (4) |
C3—C2—C1 | 124.1 (4) | C37—C36—C34 | 119.2 (4) |
C2—C3—C4 | 123.1 (4) | C37—C36—H36 | 120.4 |
C2—C3—C8 | 118.9 (4) | C34—C36—H36 | 120.4 |
C4—C3—C8 | 118.0 (4) | C36—C37—C38 | 119.5 (4) |
C5—C4—C3 | 122.4 (5) | C36—C37—H37 | 120.3 |
C5—C4—H4 | 118.8 | C38—C37—H37 | 120.3 |
C3—C4—H4 | 118.8 | N4—C38—C37 | 122.6 (4) |
C4—C5—C6 | 120.3 (5) | N4—C38—H38 | 118.7 |
C4—C5—H5 | 119.9 | C37—C38—H38 | 118.7 |
C6—C5—H5 | 119.9 | N5—C39—C40 | 122.8 (4) |
C7—C6—C5 | 120.0 (6) | N5—C39—H39 | 118.6 |
C7—C6—H6 | 120.0 | C40—C39—H39 | 118.6 |
C5—C6—H6 | 120.0 | C41—C40—C39 | 120.3 (5) |
C6—C7—C8 | 121.8 (5) | C41—C40—H40 | 119.9 |
C6—C7—H7 | 119.1 | C39—C40—H40 | 119.9 |
C8—C7—H7 | 119.1 | C40—C41—C42 | 118.7 (4) |
C7—C8—C9 | 123.2 (4) | C40—C41—H41 | 120.6 |
C7—C8—C3 | 117.5 (4) | C42—C41—H41 | 120.6 |
C9—C8—C3 | 119.3 (4) | C41—C42—C43 | 118.1 (4) |
C10—C9—C8 | 119.4 (4) | C41—C42—C44 | 123.3 (4) |
C10—C9—C12 | 117.3 (4) | C43—C42—C44 | 118.6 (5) |
C8—C9—C12 | 123.3 (4) | N5—C43—C42 | 122.4 (4) |
C9—C10—C11 | 121.7 (4) | N5—C43—C49 | 116.0 (4) |
C9—C10—H10 | 119.2 | C42—C43—C49 | 121.6 (4) |
C11—C10—H10 | 119.2 | N6—C44—C47 | 121.9 (4) |
C2—C11—C10 | 121.1 (4) | N6—C44—C42 | 118.7 (5) |
C2—C11—H11 | 119.5 | C47—C44—C42 | 119.4 (4) |
C10—C11—H11 | 119.5 | N6—C45—C46 | 123.2 (6) |
O4—C12—O3 | 124.6 (4) | N6—C45—H45 | 118.4 |
O4—C12—C9 | 121.6 (4) | C46—C45—H45 | 118.4 |
O3—C12—C9 | 113.8 (4) | C45—C46—N7 | 124.9 (5) |
O6—C13—O5 | 122.5 (4) | C45—C46—H46 | 117.6 |
O6—C13—C14 | 121.4 (4) | N7—C46—H46 | 117.6 |
O5—C13—C14 | 116.1 (4) | N7—C47—C44 | 121.8 (5) |
C23—C14—C15 | 120.5 (4) | N7—C47—C48 | 116.9 (5) |
C23—C14—C13 | 119.3 (4) | C44—C47—C48 | 121.3 (4) |
C15—C14—C13 | 120.2 (4) | C50—C48—C49 | 117.6 (5) |
C14—C15—C16 | 122.5 (4) | C50—C48—C47 | 123.9 (4) |
C14—C15—C20 | 119.1 (4) | C49—C48—C47 | 118.6 (4) |
C16—C15—C20 | 118.4 (5) | N8—C49—C48 | 123.7 (4) |
C17—C16—C15 | 121.6 (5) | N8—C49—C43 | 115.8 (3) |
C17—C16—H16 | 119.2 | C48—C49—C43 | 120.5 (4) |
C15—C16—H16 | 119.2 | C51—C50—C48 | 119.8 (4) |
C16—C17—C18 | 120.1 (6) | C51—C50—H50 | 120.1 |
C16—C17—H17 | 119.9 | C48—C50—H50 | 120.1 |
C18—C17—H17 | 119.9 | C50—C51—C52 | 119.3 (5) |
C19—C18—C17 | 120.3 (6) | C50—C51—H51 | 120.3 |
C19—C18—H18 | 119.8 | C52—C51—H51 | 120.3 |
C17—C18—H18 | 119.8 | N8—C52—C51 | 122.3 (5) |
C18—C19—C20 | 121.8 (5) | N8—C52—H52 | 118.8 |
C18—C19—H19 | 119.1 | C51—C52—H52 | 118.8 |
| | | |
O5—Cu1—O1—C1 | 93.3 (2) | Cu2iii—O7—C24—C21 | 33.8 (3) |
N4—Cu1—O1—C1 | −79.3 (2) | C22—C21—C24—O8 | −120.2 (4) |
O5i—Cu1—O1—C1 | 166.0 (2) | C20—C21—C24—O8 | 61.2 (4) |
O7ii—Cu2—O3—C12 | −90.6 (2) | C22—C21—C24—O7 | 60.2 (4) |
N8—Cu2—O3—C12 | 83.4 (2) | C20—C21—C24—O7 | −118.5 (4) |
O7iii—Cu2—O3—C12 | −165.2 (2) | C29—N1—C25—C26 | −0.2 (7) |
O1—Cu1—O5—C13 | −94.3 (3) | Cu1—N1—C25—C26 | 177.2 (4) |
N1—Cu1—O5—C13 | 89.8 (3) | N1—C25—C26—C27 | −0.8 (8) |
O5i—Cu1—O5—C13 | 179.4 (3) | C25—C26—C27—C28 | 0.9 (8) |
O1—Cu1—O5—Cu1i | 86.21 (14) | C26—C27—C28—C29 | −0.1 (7) |
N1—Cu1—O5—Cu1i | −89.68 (14) | C26—C27—C28—C30 | 178.1 (4) |
O5i—Cu1—O5—Cu1i | 0.0 | C25—N1—C29—C28 | 0.9 (6) |
O5—Cu1—N1—C25 | 4.6 (4) | Cu1—N1—C29—C28 | −176.8 (3) |
N4—Cu1—N1—C25 | 176.9 (4) | C25—N1—C29—C35 | −176.4 (4) |
O5i—Cu1—N1—C25 | −68.3 (4) | Cu1—N1—C29—C35 | 5.9 (4) |
O5—Cu1—N1—C29 | −178.0 (3) | C27—C28—C29—N1 | −0.8 (6) |
N4—Cu1—N1—C29 | −5.7 (3) | C30—C28—C29—N1 | −179.1 (4) |
O5i—Cu1—N1—C29 | 109.2 (3) | C27—C28—C29—C35 | 176.4 (4) |
O1—Cu1—N4—C38 | 11.1 (4) | C30—C28—C29—C35 | −2.0 (6) |
N1—Cu1—N4—C38 | −174.0 (4) | C31—N2—C30—C33 | −0.1 (7) |
O5i—Cu1—N4—C38 | 98.6 (4) | C31—N2—C30—C28 | −178.6 (4) |
O1—Cu1—N4—C35 | −170.4 (3) | C29—C28—C30—N2 | −177.6 (4) |
N1—Cu1—N4—C35 | 4.5 (3) | C27—C28—C30—N2 | 4.1 (7) |
O5i—Cu1—N4—C35 | −82.9 (3) | C29—C28—C30—C33 | 3.8 (6) |
O7ii—Cu2—N5—C39 | −7.6 (4) | C27—C28—C30—C33 | −174.4 (4) |
N8—Cu2—N5—C39 | 178.5 (4) | C30—N2—C31—C32 | 1.8 (8) |
O7iii—Cu2—N5—C39 | 67.5 (4) | C33—N3—C32—C31 | 0.0 (8) |
O7ii—Cu2—N5—C43 | 175.6 (3) | N2—C31—C32—N3 | −1.9 (9) |
N8—Cu2—N5—C43 | 1.6 (3) | C32—N3—C33—C30 | 1.7 (6) |
O7iii—Cu2—N5—C43 | −109.4 (3) | C32—N3—C33—C34 | −179.3 (4) |
O3—Cu2—N8—C52 | −1.7 (4) | N2—C30—C33—N3 | −1.7 (7) |
N5—Cu2—N8—C52 | 179.9 (4) | C28—C30—C33—N3 | 176.8 (4) |
O7iii—Cu2—N8—C52 | −89.1 (4) | N2—C30—C33—C34 | 179.3 (4) |
O3—Cu2—N8—C49 | 178.0 (3) | C28—C30—C33—C34 | −2.2 (6) |
N5—Cu2—N8—C49 | −0.4 (3) | N3—C33—C34—C36 | −0.4 (6) |
O7iii—Cu2—N8—C49 | 90.5 (3) | C30—C33—C34—C36 | 178.6 (4) |
Cu1—O1—C1—O2 | 6.7 (3) | N3—C33—C34—C35 | 179.8 (4) |
Cu1—O1—C1—C2 | −173.3 (2) | C30—C33—C34—C35 | −1.2 (6) |
O2—C1—C2—C11 | −47.7 (4) | C38—N4—C35—C34 | −2.0 (6) |
O1—C1—C2—C11 | 132.3 (4) | Cu1—N4—C35—C34 | 179.3 (3) |
O2—C1—C2—C3 | 132.6 (4) | C38—N4—C35—C29 | 176.0 (4) |
O1—C1—C2—C3 | −47.4 (4) | Cu1—N4—C35—C29 | −2.7 (4) |
C11—C2—C3—C4 | 179.7 (4) | C36—C34—C35—N4 | 1.1 (6) |
C1—C2—C3—C4 | −0.6 (6) | C33—C34—C35—N4 | −179.1 (4) |
C11—C2—C3—C8 | 0.5 (6) | C36—C34—C35—C29 | −176.8 (4) |
C1—C2—C3—C8 | −179.8 (3) | C33—C34—C35—C29 | 3.1 (6) |
C2—C3—C4—C5 | −177.5 (5) | N1—C29—C35—N4 | −2.1 (5) |
C8—C3—C4—C5 | 1.7 (7) | C28—C29—C35—N4 | −179.5 (4) |
C3—C4—C5—C6 | −1.2 (10) | N1—C29—C35—C34 | 175.9 (3) |
C4—C5—C6—C7 | 0.6 (11) | C28—C29—C35—C34 | −1.5 (6) |
C5—C6—C7—C8 | −0.6 (10) | C35—C34—C36—C37 | 0.6 (6) |
C6—C7—C8—C9 | 178.7 (5) | C33—C34—C36—C37 | −179.2 (4) |
C6—C7—C8—C3 | 1.2 (8) | C34—C36—C37—C38 | −1.4 (7) |
C2—C3—C8—C7 | 177.6 (4) | C35—N4—C38—C37 | 1.1 (7) |
C4—C3—C8—C7 | −1.6 (6) | Cu1—N4—C38—C37 | 179.6 (3) |
C2—C3—C8—C9 | −0.1 (6) | C36—C37—C38—N4 | 0.5 (7) |
C4—C3—C8—C9 | −179.3 (4) | C43—N5—C39—C40 | −2.5 (7) |
C7—C8—C9—C10 | −178.1 (5) | Cu2—N5—C39—C40 | −179.3 (4) |
C3—C8—C9—C10 | −0.6 (6) | N5—C39—C40—C41 | 2.9 (9) |
C7—C8—C9—C12 | 2.1 (7) | C39—C40—C41—C42 | −1.4 (9) |
C3—C8—C9—C12 | 179.6 (3) | C40—C41—C42—C43 | −0.2 (8) |
C8—C9—C10—C11 | 0.8 (7) | C40—C41—C42—C44 | −179.1 (5) |
C12—C9—C10—C11 | −179.3 (4) | C39—N5—C43—C42 | 0.8 (6) |
C3—C2—C11—C10 | −0.3 (6) | Cu2—N5—C43—C42 | 178.1 (3) |
C1—C2—C11—C10 | 180.0 (4) | C39—N5—C43—C49 | −179.8 (4) |
C9—C10—C11—C2 | −0.4 (7) | Cu2—N5—C43—C49 | −2.6 (4) |
Cu2—O3—C12—O4 | −3.8 (3) | C41—C42—C43—N5 | 0.5 (7) |
Cu2—O3—C12—C9 | 176.4 (2) | C44—C42—C43—N5 | 179.5 (4) |
C10—C9—C12—O4 | −142.3 (4) | C41—C42—C43—C49 | −178.8 (4) |
C8—C9—C12—O4 | 37.5 (4) | C44—C42—C43—C49 | 0.2 (6) |
C10—C9—C12—O3 | 37.5 (4) | C45—N6—C44—C47 | 1.4 (7) |
C8—C9—C12—O3 | −142.7 (4) | C45—N6—C44—C42 | −179.9 (5) |
Cu1—O5—C13—O6 | −7.4 (4) | C41—C42—C44—N6 | −0.2 (7) |
Cu1i—O5—C13—O6 | 171.9 (4) | C43—C42—C44—N6 | −179.1 (4) |
Cu1—O5—C13—C14 | 172.7 (3) | C41—C42—C44—C47 | 178.6 (5) |
Cu1i—O5—C13—C14 | −8.0 (4) | C43—C42—C44—C47 | −0.4 (6) |
O6—C13—C14—C23 | −91.8 (5) | C44—N6—C45—C46 | −0.4 (9) |
O5—C13—C14—C23 | 88.0 (5) | N6—C45—C46—N7 | −1.4 (11) |
O6—C13—C14—C15 | 88.7 (5) | C47—N7—C46—C45 | 1.9 (9) |
O5—C13—C14—C15 | −91.4 (5) | C46—N7—C47—C44 | −0.8 (7) |
C23—C14—C15—C16 | 178.7 (5) | C46—N7—C47—C48 | 179.9 (5) |
C13—C14—C15—C16 | −1.8 (7) | N6—C44—C47—N7 | −0.8 (7) |
C23—C14—C15—C20 | −2.2 (7) | C42—C44—C47—N7 | −179.5 (4) |
C13—C14—C15—C20 | 177.2 (4) | N6—C44—C47—C48 | 178.5 (4) |
C14—C15—C16—C17 | 179.5 (5) | C42—C44—C47—C48 | −0.3 (7) |
C20—C15—C16—C17 | 0.5 (8) | N7—C47—C48—C50 | −1.1 (7) |
C15—C16—C17—C18 | 0.0 (9) | C44—C47—C48—C50 | 179.6 (5) |
C16—C17—C18—C19 | −0.7 (9) | N7—C47—C48—C49 | −179.7 (4) |
C17—C18—C19—C20 | 1.0 (9) | C44—C47—C48—C49 | 1.1 (7) |
C18—C19—C20—C21 | 177.7 (5) | C52—N8—C49—C48 | −0.1 (6) |
C18—C19—C20—C15 | −0.5 (7) | Cu2—N8—C49—C48 | −179.8 (3) |
C14—C15—C20—C21 | 2.4 (6) | C52—N8—C49—C43 | 178.9 (4) |
C16—C15—C20—C21 | −178.5 (4) | Cu2—N8—C49—C43 | −0.8 (5) |
C14—C15—C20—C19 | −179.3 (4) | C50—C48—C49—N8 | −0.9 (7) |
C16—C15—C20—C19 | −0.2 (7) | C47—C48—C49—N8 | 177.7 (4) |
C19—C20—C21—C22 | −178.3 (4) | C50—C48—C49—C43 | −179.9 (4) |
C15—C20—C21—C22 | −0.1 (6) | C47—C48—C49—C43 | −1.2 (6) |
C19—C20—C21—C24 | 0.3 (6) | N5—C43—C49—N8 | 2.2 (5) |
C15—C20—C21—C24 | 178.5 (4) | C42—C43—C49—N8 | −178.4 (4) |
C20—C21—C22—C23 | −2.4 (7) | N5—C43—C49—C48 | −178.7 (4) |
C24—C21—C22—C23 | 178.9 (4) | C42—C43—C49—C48 | 0.6 (6) |
C15—C14—C23—C22 | −0.3 (7) | C49—C48—C50—C51 | 1.5 (7) |
C13—C14—C23—C22 | −179.7 (4) | C47—C48—C50—C51 | −177.1 (5) |
C21—C22—C23—C14 | 2.7 (7) | C48—C50—C51—C52 | −1.0 (8) |
Cu2iv—O7—C24—O8 | 10.8 (3) | C49—N8—C52—C51 | 0.6 (7) |
Cu2iii—O7—C24—O8 | −145.8 (3) | Cu2—N8—C52—C51 | −179.8 (4) |
Cu2iv—O7—C24—C21 | −169.6 (2) | C50—C51—C52—N8 | 0.0 (8) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z−1; (iii) −x+2, −y, −z+1; (iv) x, y, z+1. |
Experimental details
Crystal data |
Chemical formula | [Cu2(C12H6O4)2(C14H8N4)2]·4H2O |
Mr | 1091.97 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 12.679 (5), 14.690 (6), 14.833 (7) |
α, β, γ (°) | 69.37 (2), 82.05 (2), 65.13 (2) |
V (Å3) | 2346 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.98 |
Crystal size (mm) | 0.38 × 0.27 × 0.16 |
|
Data collection |
Diffractometer | Rigaku RAXIS-RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.618, 0.859 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 22789, 10535, 6887 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.649 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.190, 1.09 |
No. of reflections | 10535 |
No. of parameters | 667 |
No. of restraints | 436 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.03, −0.51 |
Selected bond lengths (Å) topCu1—O1 | 1.924 (3) | Cu1—N4 | 2.037 (3) |
Cu1—O5 | 1.965 (2) | Cu2—O3 | 1.916 (3) |
Cu1—O5i | 2.440 (3) | Cu2—O7ii | 1.964 (2) |
Cu1—N1 | 2.012 (3) | Cu2—O7iii | 2.348 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z−1; (iii) −x+2, −y, −z+1. |
The Cambridge Structural Database (Version 5.28, November 2006) lists several examples of metal(II) naphthalene-1,4-dicarboxylates (Maji et al., 2005; Zheng et al., 2004). The dicarboxylate group is rigid, like terephthalic acid. The copper terephthalate complex of the title heterocycle (Wang et al., 2006) has water in the coordination enviroment of the cadmium atom; the compound exists as a linear chain; one carboxyl end is chelating whereas the other is unidentate.