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metal-organic compounds
The reaction of cobalt(II) diacetate, disodium 1,3-phenyldi(oxyacetate) and 4,4′-bipyridine in water at neutral pH affords the title compound, [Co2(C10H8O6)2(C10H8N2)3(H2O)6]·C10H8N2·7H2O. The dinuclear complex is generated from a unique half-molecule by twofold symmetry; it contains a bridging 4,4′-bipyridine molecule connected to two cobalt(II) atoms, each of which is covalently bonded to a carboxylate unit, another 4,4′-bipyridine molecule and three water molecules in octahedral geometry. The non-coordinated 4,4′-bipyridine molecule is stacked over the bridging 4,4′-bipyridine molecule at a separation of about 3.5 Å, and accepts hydrogen bonds at each N atom from coordinated water molecules.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804024535/hb6203sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804024535/hb6203Isup2.hkl |
CCDC reference: 255410
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- H-atom completeness 98%
- Disorder in solvent or counterion
- R factor = 0.032
- wR factor = 0.078
- Data-to-parameter ratio = 13.2
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.607 0.894 Tmin' and Tmax expected: 0.791 0.891 RR' = 0.765 Please check that your absorption correction is appropriate. 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 ............. 0.76 PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.95 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 20.00 Perc. PLAT417_ALERT_2_C Short Inter D-H..H-D H1W2 .. H4W2 .. 2.11 Ang. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 4 O2W -CO1 -O1 -C21 13.00 0.90 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 8 N3 -CO1 -N1 -C10 -33.90 1.30 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 13 N3 -CO1 -N1 -C1 145.90 1.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 19 N1 -CO1 -N3 -C15 -157.60 1.10 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 24 N1 -CO1 -N3 -C11 25.80 1.30 1.555 1.555 1.555 1.555 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 12 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat O2W -H2W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat O2W -H2W2 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat O3W -H3W2 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat O4W -H4W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat O4W -H4W2 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat O5W -H5W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.86(4), Rep 0.850(10) ...... 4.00 su-Rat O5W -H5W2 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat O7W -H7W1 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat O2W -H3# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat O2W -H4# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat O3W -H6# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat O4W -H8# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat O4W -H7# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(4), Rep 0.850(10) ...... 4.00 su-Rat O5W -H10# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat O5W -H9# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat O7W -H12# 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 2.04(4), Rep 2.040(10) ...... 4.00 su-Rat H4# -N4 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.92(3), Rep 1.910(10) ...... 3.00 su-Rat H6# -O4W 1.555 1.565 PLAT736_ALERT_1_C H...A Calc 1.91(3), Rep 1.910(10) ...... 3.00 su-Rat H7# -N2 1.555 4.545 PLAT736_ALERT_1_C H...A Calc 2.01(4), Rep 2.020(10) ...... 4.00 su-Rat H10# -O6 1.555 1.554 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 6 H O
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:C60 H74 Co2 N8 O25 Atom count from the _atom_site data: C60 H72 Co2 N8 O25 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 C60 H74 Co2 N8 O25 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 120.00 120.00 0.00 H 148.00 144.00 4.00 Co 4.00 4.00 0.00 N 16.00 16.00 0.00 O 50.00 50.00 0.00 REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 6280 Count of symmetry unique reflns 3984 Completeness (_total/calc) 157.63% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2296 Fraction of Friedel pairs measured 0.576 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 36 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 26 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 9 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-II (Johnson, 1976); software used to prepare material for publication: SHELXL97.
(I) top
Crystal data top
3C10H8N2·2C10H8O6·6H2O·2Co·C10H8N2·7H2O | F(000) = 1488 |
Mr = 1425.13 | Dx = 1.473 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 13866 reflections |
a = 34.738 (4) Å | θ = 3.2–28.0° |
b = 7.450 (2) Å | µ = 0.61 mm−1 |
c = 12.929 (4) Å | T = 295 K |
β = 106.23 (2)° | Prism, pink |
V = 3213 (1) Å3 | 0.38 × 0.24 × 0.19 mm |
Z = 2 |
Data collection top
Rigaku RAPID-RAXIS diffractometer | 6280 independent reflections |
Radiation source: fine-focus sealed tube | 5750 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ω scan | θmax = 27.5°, θmin = 3.2° |
Absorption correction: multi-scan ABSCOR (Higashi, 1995) | h = −44→44 |
Tmin = 0.607, Tmax = 0.894 | k = −9→8 |
14697 measured reflections | l = −16→16 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.078 | w = 1/[σ2(Fo2) + (0.0496P)2 + 0.6741P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
6280 reflections | Δρmax = 0.56 e Å−3 |
475 parameters | Δρmin = −0.19 e Å−3 |
19 restraints | Absolute structure: Flack (1983) parameter; 2337 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.02 (1) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Co1 | 0.121893 (7) | 0.50000 (4) | 0.284207 (18) | 0.02858 (7) | |
O1 | 0.16370 (5) | 0.6630 (2) | 0.40492 (12) | 0.0348 (4) | |
O2 | 0.20211 (5) | 0.4578 (2) | 0.51266 (13) | 0.0447 (4) | |
O3 | 0.20032 (5) | 0.9299 (2) | 0.55410 (13) | 0.0435 (4) | |
O4 | 0.12071 (5) | 0.6800 (3) | 0.76627 (13) | 0.0431 (4) | |
O5 | 0.04932 (6) | 0.5487 (3) | 0.90235 (15) | 0.0535 (5) | |
O6 | 0.08562 (6) | 0.3870 (3) | 0.82125 (16) | 0.0519 (5) | |
O1w | 0.14540 (5) | 0.2786 (2) | 0.37430 (13) | 0.0376 (4) | |
H1w1 | 0.1667 (5) | 0.320 (3) | 0.4166 (19) | 0.050 (6)* | |
H1w2 | 0.1508 (7) | 0.181 (2) | 0.347 (2) | 0.050 (6)* | |
O2w | 0.08269 (5) | 0.3186 (3) | 0.17482 (14) | 0.0419 (4) | |
H2w1 | 0.0614 (7) | 0.344 (6) | 0.126 (2) | 0.113 (12)* | |
H2w2 | 0.0782 (11) | 0.230 (4) | 0.211 (3) | 0.113 (12)* | |
O3w | 0.09848 (6) | 0.7306 (3) | 0.19601 (15) | 0.0445 (4) | |
H3w1 | 0.0800 (7) | 0.752 (4) | 0.1386 (16) | 0.072 (8)* | |
H3w2 | 0.1140 (8) | 0.820 (3) | 0.212 (2) | 0.072 (8)* | |
O4w | 0.15753 (5) | −0.0281 (3) | 0.28573 (13) | 0.0431 (4) | |
H4w1 | 0.1747 (7) | −0.026 (6) | 0.250 (2) | 0.088 (8)* | |
H4w2 | 0.1670 (9) | −0.091 (5) | 0.3419 (19) | 0.088 (8)* | |
O5w | 0.09063 (7) | 0.1294 (3) | −0.01240 (18) | 0.0628 (5) | |
H5w1 | 0.0690 (7) | 0.078 (5) | −0.010 (3) | 0.117 (12)* | |
H5w2 | 0.0851 (11) | 0.209 (5) | −0.062 (3) | 0.117 (12)* | |
O6w | 0.01174 (12) | 0.3684 (8) | 0.0371 (3) | 0.0648 (12) | 0.50 |
H6w1 | −0.0116 (6) | 0.408 (4) | 0.0356 (15) | 0.062 (10)* | |
O7w | 0.04108 (6) | −0.1567 (3) | 0.01328 (16) | 0.0579 (5) | |
H7w1 | 0.0435 (10) | −0.236 (4) | −0.032 (2) | 0.072 (11)* | |
N1 | 0.16420 (5) | 0.4881 (4) | 0.18894 (12) | 0.0344 (4) | |
N2 | 0.29244 (6) | 0.4650 (3) | −0.15385 (16) | 0.0483 (6) | |
N3 | 0.07732 (5) | 0.5263 (3) | 0.36936 (13) | 0.0325 (4) | |
N4 | 0.04939 (8) | 0.0724 (4) | 0.29504 (19) | 0.0592 (6) | |
C1 | 0.20375 (6) | 0.4682 (4) | 0.22911 (15) | 0.0409 (6) | |
H1 | 0.2142 | 0.4582 | 0.3034 | 0.049* | |
C2 | 0.22986 (7) | 0.4617 (4) | 0.16644 (16) | 0.0422 (7) | |
H2 | 0.2572 | 0.4475 | 0.1987 | 0.051* | |
C3 | 0.21554 (6) | 0.4765 (3) | 0.05514 (15) | 0.0319 (5) | |
C4 | 0.24256 (6) | 0.4725 (4) | −0.01655 (16) | 0.0342 (5) | |
C5 | 0.28356 (6) | 0.4990 (5) | 0.02230 (17) | 0.0437 (5) | |
H5 | 0.2952 | 0.5194 | 0.0953 | 0.052* | |
C6 | 0.30698 (7) | 0.4950 (6) | −0.04822 (19) | 0.0506 (6) | |
H6 | 0.3344 | 0.5143 | −0.0206 | 0.061* | |
C7 | 0.25325 (8) | 0.4385 (4) | −0.19056 (19) | 0.0494 (7) | |
H7 | 0.2426 | 0.4162 | −0.2638 | 0.059* | |
C8 | 0.22736 (8) | 0.4421 (4) | −0.12691 (18) | 0.0465 (6) | |
H8 | 0.2000 | 0.4244 | −0.1573 | 0.056* | |
C9 | 0.17456 (6) | 0.4967 (6) | 0.01363 (15) | 0.0452 (5) | |
H9 | 0.1633 | 0.5070 | −0.0604 | 0.054* | |
C10 | 0.15042 (6) | 0.5017 (6) | 0.08200 (15) | 0.0427 (5) | |
H10 | 0.1229 | 0.5153 | 0.0519 | 0.051* | |
C11 | 0.03951 (6) | 0.5725 (4) | 0.31675 (16) | 0.0362 (5) | |
H11 | 0.0337 | 0.6027 | 0.2442 | 0.043* | |
C12 | 0.00895 (6) | 0.5771 (4) | 0.36527 (17) | 0.0368 (5) | |
H12 | −0.0168 | 0.6084 | 0.3252 | 0.044* | |
C13 | 0.01643 (6) | 0.5352 (3) | 0.47358 (15) | 0.0303 (5) | |
C14 | 0.05567 (6) | 0.4917 (4) | 0.52905 (14) | 0.0356 (4) | |
H14 | 0.0623 | 0.4641 | 0.6021 | 0.043* | |
C15 | 0.08474 (6) | 0.4898 (4) | 0.47445 (15) | 0.0357 (4) | |
H15 | 0.1109 | 0.4615 | 0.5130 | 0.043* | |
C16 | 0.01032 (10) | 0.1094 (5) | 0.2759 (2) | 0.0587 (8) | |
H16 | −0.0036 | 0.1483 | 0.2073 | 0.070* | |
C17 | −0.01032 (8) | 0.0931 (4) | 0.3521 (2) | 0.0488 (6) | |
H17 | −0.0377 | 0.1174 | 0.3342 | 0.059* | |
C18 | 0.01015 (7) | 0.0400 (3) | 0.45617 (18) | 0.0386 (5) | |
C19 | 0.05041 (7) | −0.0016 (5) | 0.47553 (17) | 0.0448 (5) | |
H19 | 0.0651 | −0.0408 | 0.5434 | 0.054* | |
C20 | 0.06873 (8) | 0.0153 (5) | 0.3941 (2) | 0.0540 (6) | |
H20 | 0.0957 | −0.0144 | 0.4086 | 0.065* | |
C21 | 0.19222 (6) | 0.6157 (3) | 0.48386 (17) | 0.0318 (5) | |
C22 | 0.21882 (7) | 0.7607 (4) | 0.55125 (18) | 0.0396 (5) | |
H22a | 0.2288 | 0.7169 | 0.6245 | 0.048* | |
H22b | 0.2418 | 0.7783 | 0.5236 | 0.048* | |
C23 | 0.17512 (7) | 0.9454 (3) | 0.61946 (16) | 0.0355 (5) | |
C24 | 0.16575 (8) | 1.1203 (4) | 0.64097 (19) | 0.0394 (6) | |
H24 | 0.1760 | 1.2167 | 0.6115 | 0.047* | |
C25 | 0.14104 (8) | 1.1498 (4) | 0.7064 (2) | 0.0418 (6) | |
H25 | 0.1346 | 1.2668 | 0.7204 | 0.050* | |
C26 | 0.12557 (6) | 1.0070 (4) | 0.75172 (15) | 0.0378 (4) | |
H26 | 0.1093 | 1.0278 | 0.7966 | 0.045* | |
C27 | 0.13496 (7) | 0.8325 (4) | 0.72846 (18) | 0.0345 (5) | |
C28 | 0.15987 (7) | 0.8012 (3) | 0.66234 (17) | 0.0357 (5) | |
H28 | 0.1661 | 0.6844 | 0.6473 | 0.043* | |
C29 | 0.09204 (7) | 0.7058 (4) | 0.82536 (19) | 0.0388 (5) | |
H29a | 0.0705 | 0.7815 | 0.7840 | 0.047* | |
H29b | 0.1048 | 0.7671 | 0.8924 | 0.047* | |
C30 | 0.07453 (6) | 0.5282 (4) | 0.85020 (15) | 0.0372 (6) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.02808 (12) | 0.03159 (14) | 0.02793 (11) | 0.00008 (13) | 0.01090 (9) | −0.00005 (13) |
O1 | 0.0387 (9) | 0.0308 (9) | 0.0344 (8) | −0.0026 (7) | 0.0094 (7) | −0.0012 (6) |
O2 | 0.0459 (9) | 0.0388 (11) | 0.0428 (8) | 0.0003 (7) | 0.0017 (7) | 0.0008 (7) |
O3 | 0.0566 (10) | 0.0395 (9) | 0.0413 (8) | −0.0112 (7) | 0.0251 (8) | −0.0055 (7) |
O4 | 0.0492 (10) | 0.0394 (10) | 0.0476 (9) | −0.0008 (8) | 0.0247 (8) | 0.0027 (8) |
O5 | 0.0551 (11) | 0.0549 (14) | 0.0610 (10) | −0.0068 (8) | 0.0337 (9) | −0.0018 (9) |
O6 | 0.0621 (12) | 0.0432 (11) | 0.0570 (11) | −0.0008 (9) | 0.0277 (9) | −0.0001 (9) |
O1w | 0.0423 (10) | 0.0308 (8) | 0.0377 (8) | 0.0032 (7) | 0.0078 (7) | −0.0035 (7) |
O2w | 0.0388 (10) | 0.0531 (12) | 0.0343 (8) | −0.0097 (8) | 0.0109 (7) | −0.0025 (8) |
O3w | 0.0427 (11) | 0.0400 (10) | 0.0483 (10) | 0.0044 (8) | 0.0086 (8) | 0.0078 (8) |
O4w | 0.0533 (9) | 0.0357 (11) | 0.0470 (8) | 0.0024 (8) | 0.0252 (7) | 0.0013 (8) |
O5w | 0.0668 (13) | 0.0561 (14) | 0.0731 (14) | −0.0004 (10) | 0.0323 (11) | 0.0099 (11) |
O6w | 0.044 (2) | 0.092 (4) | 0.060 (2) | 0.015 (2) | 0.0169 (17) | 0.022 (2) |
O7w | 0.0580 (12) | 0.0583 (13) | 0.0572 (11) | −0.0049 (10) | 0.0157 (9) | −0.0028 (10) |
N1 | 0.0294 (8) | 0.0434 (10) | 0.0313 (7) | 0.0010 (10) | 0.0097 (6) | 0.0005 (11) |
N2 | 0.0512 (12) | 0.0495 (16) | 0.0536 (11) | 0.0004 (10) | 0.0305 (9) | 0.0010 (11) |
N3 | 0.0307 (8) | 0.0359 (13) | 0.0325 (7) | 0.0001 (8) | 0.0112 (6) | 0.0006 (8) |
N4 | 0.0646 (16) | 0.0641 (16) | 0.0563 (13) | −0.0191 (12) | 0.0291 (12) | −0.0050 (12) |
C1 | 0.0353 (11) | 0.0592 (18) | 0.0275 (9) | 0.0075 (11) | 0.0077 (8) | 0.0042 (11) |
C2 | 0.0276 (10) | 0.066 (2) | 0.0319 (9) | 0.0078 (10) | 0.0061 (8) | 0.0028 (11) |
C3 | 0.0297 (9) | 0.0345 (13) | 0.0323 (9) | −0.0004 (10) | 0.0100 (7) | −0.0010 (10) |
C4 | 0.0333 (10) | 0.0376 (15) | 0.0346 (9) | 0.0006 (10) | 0.0141 (8) | 0.0018 (10) |
C5 | 0.0326 (10) | 0.0582 (14) | 0.0422 (10) | −0.0007 (15) | 0.0134 (8) | −0.0052 (16) |
C6 | 0.0369 (11) | 0.0632 (16) | 0.0565 (13) | 0.0030 (16) | 0.0208 (10) | 0.0020 (19) |
C7 | 0.0527 (15) | 0.0634 (19) | 0.0374 (11) | −0.0014 (12) | 0.0213 (11) | −0.0022 (11) |
C8 | 0.0391 (12) | 0.0657 (19) | 0.0354 (10) | −0.0073 (11) | 0.0118 (9) | −0.0036 (11) |
C9 | 0.0305 (10) | 0.0779 (17) | 0.0260 (8) | 0.0043 (16) | 0.0060 (7) | 0.0012 (15) |
C10 | 0.0258 (9) | 0.0713 (16) | 0.0307 (9) | 0.0019 (14) | 0.0073 (7) | 0.0020 (15) |
C11 | 0.0317 (11) | 0.0500 (14) | 0.0276 (9) | 0.0001 (9) | 0.0095 (8) | 0.0029 (9) |
C12 | 0.0264 (10) | 0.0510 (14) | 0.0311 (10) | 0.0006 (9) | 0.0051 (8) | 0.0017 (10) |
C13 | 0.0296 (10) | 0.0307 (13) | 0.0323 (9) | −0.0008 (8) | 0.0115 (8) | −0.0028 (8) |
C14 | 0.0314 (9) | 0.0463 (12) | 0.0306 (8) | 0.0047 (13) | 0.0110 (7) | 0.0028 (13) |
C15 | 0.0287 (9) | 0.0459 (12) | 0.0335 (9) | 0.0036 (12) | 0.0101 (7) | 0.0003 (13) |
C16 | 0.069 (2) | 0.0631 (19) | 0.0434 (14) | −0.0111 (15) | 0.0144 (13) | 0.0067 (14) |
C17 | 0.0467 (14) | 0.0512 (16) | 0.0472 (13) | −0.0039 (12) | 0.0109 (11) | 0.0021 (12) |
C18 | 0.0433 (12) | 0.0296 (14) | 0.0436 (11) | −0.0048 (9) | 0.0132 (10) | −0.0026 (9) |
C19 | 0.0418 (11) | 0.0447 (12) | 0.0472 (11) | 0.0002 (15) | 0.0112 (9) | −0.0013 (16) |
C20 | 0.0493 (13) | 0.0581 (18) | 0.0592 (14) | −0.0128 (16) | 0.0225 (11) | −0.0035 (17) |
C21 | 0.0316 (11) | 0.0363 (12) | 0.0304 (10) | −0.0024 (9) | 0.0136 (9) | −0.0013 (9) |
C22 | 0.0370 (12) | 0.0446 (14) | 0.0389 (11) | −0.0104 (10) | 0.0135 (10) | −0.0071 (10) |
C23 | 0.0396 (12) | 0.0386 (14) | 0.0275 (9) | −0.0069 (9) | 0.0083 (8) | −0.0035 (9) |
C24 | 0.0485 (14) | 0.0317 (13) | 0.0379 (12) | −0.0058 (10) | 0.0118 (10) | 0.0013 (11) |
C25 | 0.0477 (15) | 0.0323 (13) | 0.0423 (13) | 0.0037 (10) | 0.0072 (11) | −0.0051 (11) |
C26 | 0.0371 (10) | 0.0425 (12) | 0.0334 (9) | 0.0026 (12) | 0.0093 (7) | −0.0048 (13) |
C27 | 0.0326 (12) | 0.0401 (13) | 0.0300 (10) | −0.0025 (9) | 0.0075 (9) | −0.0005 (10) |
C28 | 0.0396 (12) | 0.0338 (13) | 0.0347 (11) | −0.0024 (10) | 0.0122 (9) | −0.0025 (10) |
C29 | 0.0367 (12) | 0.0429 (14) | 0.0391 (12) | −0.0015 (10) | 0.0141 (10) | −0.0007 (11) |
C30 | 0.0310 (10) | 0.0510 (17) | 0.0276 (9) | −0.0002 (10) | 0.0051 (7) | 0.0012 (11) |
Geometric parameters (Å, º) top
Co1—O1 | 2.180 (2) | C5—H5 | 0.9300 |
Co1—O1w | 2.053 (2) | C6—H6 | 0.9300 |
Co1—O2w | 2.146 (2) | C7—C8 | 1.379 (3) |
Co1—O3w | 2.097 (2) | C7—H7 | 0.9300 |
Co1—N1 | 2.167 (2) | C8—H8 | 0.9300 |
Co1—N3 | 2.145 (2) | C9—C10 | 1.379 (3) |
O1—C21 | 1.258 (3) | C9—H9 | 0.9300 |
O2—C21 | 1.253 (3) | C10—H10 | 0.9300 |
O3—C23 | 1.381 (3) | C11—C12 | 1.376 (3) |
O3—C22 | 1.420 (3) | C11—H11 | 0.9300 |
O4—C27 | 1.382 (3) | C12—C13 | 1.386 (3) |
O4—C29 | 1.428 (3) | C12—H12 | 0.9300 |
O5—C30 | 1.255 (3) | C13—C14 | 1.390 (3) |
O6—C30 | 1.215 (3) | C13—C13i | 1.485 (4) |
O1w—H1w1 | 0.85 (1) | C14—C15 | 1.384 (3) |
O1w—H1w2 | 0.85 (1) | C14—H14 | 0.9300 |
O2w—H2w1 | 0.85 (1) | C15—H15 | 0.9300 |
O2w—H2w2 | 0.85 (1) | C16—C17 | 1.377 (4) |
O3w—H3w1 | 0.85 (1) | C16—H16 | 0.9300 |
O3w—H3w2 | 0.85 (1) | C17—C18 | 1.392 (3) |
O4w—H4w1 | 0.85 (1) | C17—H17 | 0.9300 |
O4w—H4w2 | 0.85 (1) | C18—C19 | 1.385 (3) |
O5w—H5w1 | 0.85 (1) | C18—C18i | 1.493 (4) |
O5w—H5w2 | 0.85 (1) | C19—C20 | 1.380 (3) |
O6w—H6w1 | 0.86 (1) | C19—H19 | 0.9300 |
O7w—H7w1 | 0.85 (1) | C20—H20 | 0.9300 |
N1—C10 | 1.335 (2) | C21—C22 | 1.526 (3) |
N1—C1 | 1.334 (3) | C22—H22a | 0.9700 |
N2—C7 | 1.325 (3) | C22—H22b | 0.9700 |
N2—C6 | 1.336 (3) | C23—C28 | 1.381 (3) |
N3—C15 | 1.338 (2) | C23—C24 | 1.389 (4) |
N3—C11 | 1.344 (3) | C24—C25 | 1.381 (4) |
N4—C16 | 1.338 (4) | C24—H24 | 0.9300 |
N4—C20 | 1.338 (4) | C25—C26 | 1.392 (4) |
C1—C2 | 1.375 (3) | C25—H25 | 0.9300 |
C1—H1 | 0.9300 | C26—C27 | 1.394 (4) |
C2—C3 | 1.389 (3) | C26—H26 | 0.9300 |
C2—H2 | 0.9300 | C27—C28 | 1.396 (3) |
C3—C9 | 1.382 (3) | C28—H28 | 0.9300 |
C3—C4 | 1.492 (3) | C29—C30 | 1.527 (4) |
C4—C5 | 1.386 (3) | C29—H29a | 0.9700 |
C4—C8 | 1.394 (3) | C29—H29b | 0.9700 |
C5—C6 | 1.382 (3) | ||
O1—Co1—O1w | 87.80 (7) | N3—C11—C12 | 123.02 (19) |
O1—Co1—O2w | 174.70 (7) | N3—C11—H11 | 118.5 |
O1—Co1—O3w | 90.72 (7) | C12—C11—H11 | 118.5 |
O1—Co1—N1 | 90.45 (7) | C11—C12—C13 | 120.3 (2) |
O1—Co1—N3 | 90.78 (7) | C11—C12—H12 | 119.9 |
O1w—Co1—O2w | 86.92 (8) | C13—C12—H12 | 119.9 |
O1w—Co1—O3w | 178.41 (8) | C12—C13—C14 | 116.96 (18) |
O1w—Co1—N1 | 93.68 (8) | C12—C13—C13i | 120.9 (2) |
O1w—Co1—N3 | 90.68 (7) | C14—C13—C13i | 122.1 (2) |
O2w—Co1—O3w | 94.56 (9) | C15—C14—C13 | 119.30 (18) |
O2w—Co1—N1 | 90.33 (7) | C15—C14—H14 | 120.4 |
O2w—Co1—N3 | 88.84 (7) | C13—C14—H14 | 120.4 |
O3w—Co1—N1 | 86.90 (9) | N3—C15—C14 | 123.69 (18) |
O3w—Co1—N3 | 88.76 (8) | N3—C15—H15 | 118.2 |
N1—Co1—N3 | 175.51 (8) | C14—C15—H15 | 118.2 |
C21—O1—Co1 | 129.89 (15) | N4—C16—C17 | 123.6 (3) |
C23—O3—C22 | 117.32 (18) | N4—C16—H16 | 118.2 |
C27—O4—C29 | 116.82 (19) | C17—C16—H16 | 118.2 |
Co1—O1w—H1w1 | 102 (2) | C16—C17—C18 | 119.3 (3) |
Co1—O1w—H1w2 | 123 (2) | C16—C17—H17 | 120.3 |
H1w1—O1w—H1w2 | 109 (2) | C18—C17—H17 | 120.3 |
Co1—O2w—H2w1 | 128 (3) | C19—C18—C17 | 117.1 (2) |
Co1—O2w—H2w2 | 108 (3) | C19—C18—C18i | 122.0 (3) |
H2w1—O2w—H2w2 | 109 (2) | C17—C18—C18i | 120.8 (3) |
Co1—O3w—H3w1 | 135 (2) | C18—C19—C20 | 120.0 (2) |
Co1—O3w—H3w2 | 113 (2) | C18—C19—H19 | 120.0 |
H3w1—O3w—H3w2 | 110 (2) | C20—C19—H19 | 120.0 |
H4w1—O4w—H4w2 | 108 (2) | N4—C20—C19 | 122.9 (3) |
H5w1—O5w—H5w2 | 109 (2) | N4—C20—H20 | 118.5 |
C10—N1—C1 | 116.34 (17) | C19—C20—H20 | 118.5 |
C10—N1—Co1 | 118.82 (13) | O2—C21—O1 | 126.3 (2) |
C1—N1—Co1 | 124.85 (13) | O2—C21—C22 | 115.02 (19) |
C7—N2—C6 | 116.62 (19) | O1—C21—C22 | 118.6 (2) |
C15—N3—C11 | 116.71 (17) | O3—C22—C21 | 115.91 (19) |
C15—N3—Co1 | 122.73 (14) | O3—C22—H22a | 108.3 |
C11—N3—Co1 | 120.47 (13) | C21—C22—H22a | 108.3 |
C16—N4—C20 | 117.0 (2) | O3—C22—H22b | 108.3 |
N1—C1—C2 | 123.46 (18) | C21—C22—H22b | 108.3 |
N1—C1—H1 | 118.3 | H22a—C22—H22b | 107.4 |
C2—C1—H1 | 118.3 | O3—C23—C28 | 124.1 (2) |
C1—C2—C3 | 120.22 (19) | O3—C23—C24 | 115.2 (2) |
C1—C2—H2 | 119.9 | C28—C23—C24 | 120.8 (2) |
C3—C2—H2 | 119.9 | C25—C24—C23 | 119.5 (2) |
C9—C3—C2 | 116.26 (18) | C25—C24—H24 | 120.2 |
C9—C3—C4 | 121.28 (17) | C23—C24—H24 | 120.2 |
C2—C3—C4 | 122.45 (18) | C24—C25—C26 | 121.0 (2) |
C5—C4—C8 | 116.79 (19) | C24—C25—H25 | 119.5 |
C5—C4—C3 | 122.22 (17) | C26—C25—H25 | 119.5 |
C8—C4—C3 | 120.99 (19) | C25—C26—C27 | 118.7 (2) |
C6—C5—C4 | 119.54 (19) | C25—C26—H26 | 120.6 |
C6—C5—H5 | 120.2 | C27—C26—H26 | 120.6 |
C4—C5—H5 | 120.2 | O4—C27—C28 | 115.1 (2) |
N2—C6—C5 | 123.6 (2) | O4—C27—C26 | 124.2 (2) |
N2—C6—H6 | 118.2 | C28—C27—C26 | 120.7 (2) |
C5—C6—H6 | 118.2 | C23—C28—C27 | 119.3 (2) |
N2—C7—C8 | 124.0 (2) | C23—C28—H28 | 120.4 |
N2—C7—H7 | 118.0 | C27—C28—H28 | 120.4 |
C8—C7—H7 | 118.0 | O4—C29—C30 | 112.0 (2) |
C7—C8—C4 | 119.4 (2) | O4—C29—H29a | 109.2 |
C7—C8—H8 | 120.3 | C30—C29—H29a | 109.2 |
C4—C8—H8 | 120.3 | O4—C29—H29b | 109.2 |
C10—C9—C3 | 119.94 (17) | C30—C29—H29b | 109.2 |
C10—C9—H9 | 120.0 | H29a—C29—H29b | 107.9 |
C3—C9—H9 | 120.0 | O6—C30—O5 | 126.9 (2) |
N1—C10—C9 | 123.78 (18) | O6—C30—C29 | 120.40 (19) |
N1—C10—H10 | 118.1 | O5—C30—C29 | 112.7 (2) |
C9—C10—H10 | 118.1 | ||
O1w—Co1—O1—C21 | 8.21 (19) | C1—N1—C10—C9 | −0.2 (6) |
O3w—Co1—O1—C21 | −172.37 (19) | Co1—N1—C10—C9 | 179.7 (3) |
N3—Co1—O1—C21 | 98.86 (19) | C3—C9—C10—N1 | 0.1 (6) |
O2w—Co1—O1—C21 | 13.0 (9) | C15—N3—C11—C12 | −2.2 (4) |
N1—Co1—O1—C21 | −85.5 (2) | Co1—N3—C11—C12 | 174.5 (2) |
O1w—Co1—N1—C10 | 132.3 (3) | N3—C11—C12—C13 | 0.8 (4) |
O3w—Co1—N1—C10 | −49.2 (3) | C11—C12—C13—C14 | 0.8 (4) |
N3—Co1—N1—C10 | −33.9 (13) | C11—C12—C13—C13i | −178.48 (18) |
O2w—Co1—N1—C10 | 45.4 (3) | C12—C13—C14—C15 | −0.8 (4) |
O1—Co1—N1—C10 | −139.9 (3) | C13i—C13—C14—C15 | 178.4 (2) |
O1w—Co1—N1—C1 | −47.8 (3) | C11—N3—C15—C14 | 2.2 (4) |
O3w—Co1—N1—C1 | 130.7 (3) | Co1—N3—C15—C14 | −174.5 (2) |
N3—Co1—N1—C1 | 145.9 (10) | C13—C14—C15—N3 | −0.7 (5) |
O2w—Co1—N1—C1 | −134.8 (3) | C20—N4—C16—C17 | 0.6 (5) |
O1—Co1—N1—C1 | 40.0 (3) | N4—C16—C17—C18 | 1.8 (5) |
O1w—Co1—N3—C15 | 36.1 (2) | C16—C17—C18—C19 | −2.8 (4) |
O3w—Co1—N3—C15 | −142.4 (2) | C16—C17—C18—C18i | 173.3 (2) |
O2w—Co1—N3—C15 | 123.1 (2) | C17—C18—C19—C20 | 1.7 (4) |
N1—Co1—N3—C15 | −157.6 (11) | C18i—C18—C19—C20 | −174.4 (2) |
O1—Co1—N3—C15 | −51.7 (2) | C16—N4—C20—C19 | −1.7 (5) |
O1w—Co1—N3—C11 | −140.42 (19) | C18—C19—C20—N4 | 0.6 (5) |
O3w—Co1—N3—C11 | 41.1 (2) | Co1—O1—C21—O2 | −2.6 (4) |
O2w—Co1—N3—C11 | −53.5 (2) | Co1—O1—C21—C22 | 175.54 (14) |
N1—Co1—N3—C11 | 25.8 (13) | C23—O3—C22—C21 | 77.1 (2) |
O1—Co1—N3—C11 | 131.77 (19) | O2—C21—C22—O3 | −153.5 (2) |
C10—N1—C1—C2 | 0.1 (5) | O1—C21—C22—O3 | 28.1 (3) |
Co1—N1—C1—C2 | −179.8 (2) | C22—O3—C23—C28 | −15.1 (3) |
N1—C1—C2—C3 | 0.1 (5) | C22—O3—C23—C24 | 164.6 (2) |
C1—C2—C3—C9 | −0.2 (4) | O3—C23—C24—C25 | −179.4 (2) |
C1—C2—C3—C4 | 179.3 (3) | C28—C23—C24—C25 | 0.3 (4) |
C9—C3—C4—C5 | 162.9 (3) | C23—C24—C25—C26 | 0.4 (4) |
C2—C3—C4—C5 | −16.6 (4) | C24—C25—C26—C27 | −1.0 (3) |
C9—C3—C4—C8 | −16.9 (4) | C29—O4—C27—C28 | −174.01 (19) |
C2—C3—C4—C8 | 163.7 (3) | C29—O4—C27—C26 | 5.3 (3) |
C8—C4—C5—C6 | 0.2 (5) | C25—C26—C27—O4 | −178.4 (2) |
C3—C4—C5—C6 | −179.5 (3) | C25—C26—C27—C28 | 0.9 (3) |
C7—N2—C6—C5 | 0.2 (6) | O3—C23—C28—C27 | 179.3 (2) |
C4—C5—C6—N2 | −0.6 (6) | C24—C23—C28—C27 | −0.4 (3) |
C6—N2—C7—C8 | 0.6 (5) | O4—C27—C28—C23 | 179.1 (2) |
N2—C7—C8—C4 | −1.0 (4) | C26—C27—C28—C23 | −0.3 (3) |
C5—C4—C8—C7 | 0.5 (4) | C27—O4—C29—C30 | 172.60 (18) |
C3—C4—C8—C7 | −179.7 (3) | O4—C29—C30—O6 | 0.7 (3) |
C2—C3—C9—C10 | 0.1 (5) | O4—C29—C30—O5 | 179.86 (18) |
C4—C3—C9—C10 | −179.4 (3) |
Symmetry code: (i) −x, y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O2 | 0.85 (1) | 1.80 (1) | 2.625 (2) | 163 (2) |
O1w—H1w2···O4w | 0.85 (1) | 1.79 (1) | 2.642 (3) | 175 (2) |
O2w—H2w1···O6w | 0.85 (1) | 1.80 (1) | 2.632 (4) | 169 (4) |
O2w—H2w2···N4 | 0.85 (1) | 2.04 (1) | 2.850 (3) | 159 (4) |
O3w—H3w2···O4wii | 0.85 (1) | 1.91 (1) | 2.730 (3) | 161 (3) |
O3w—H3w1···O7wii | 0.85 (1) | 1.92 (1) | 2.762 (3) | 170 (3) |
O4w—H4w2···O1iii | 0.85 (1) | 2.02 (3) | 2.745 (3) | 143 (4) |
O4w—H4w1···N2iv | 0.85 (1) | 1.91 (1) | 2.755 (2) | 172 (4) |
O5w—H5w2···O6v | 0.85 (1) | 2.02 (1) | 2.851 (3) | 166 (4) |
O5w—H5w1···O7w | 0.85 (1) | 2.06 (2) | 2.817 (3) | 147 (4) |
O6w—H6w1···O5i | 0.86 (1) | 2.01 (2) | 2.801 (5) | 152 (3) |
O7w—H7w1···O5vi | 0.85 (1) | 1.85 (2) | 2.680 (3) | 164 (4) |
Symmetry codes: (i) −x, y, −z+1; (ii) x, y+1, z; (iii) x, y−1, z; (iv) −x+1/2, y−1/2, −z; (v) x, y, z−1; (vi) x, y−1, z−1. |
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