In the title compound, {[Co(C
8H
3NO
6)(C
10H
8N
2)(H
2O)]·0.25H
2O}
n, the coordination polyhedron of the Co
II ion is an octahedron. Each pair of adjacent Co
II ions is bridged by a dianion of 5-nitro-1,3-benzenedicarboxylic acid (H
2nmbdc) to form a chain running along the
a axis. These chains are linked by π–π stacking interactions and O(water)—H
O hydrogen bonds into a supramolecular structure.
Supporting information
CCDC reference: 298380
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- Disorder in solvent or counterion
- R factor = 0.038
- wR factor = 0.112
- Data-to-parameter ratio = 12.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.12 Ratio
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT213_ALERT_2_C Atom O6 has ADP max/min Ratio ............. 3.60 prolat
PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 3.43 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O8
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc.
PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat
O13W -H13B 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Rat
O13W -H13B 1.555 1.555
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
14 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL.
catena-Poly[[aqua(2,2'-bipyridine)cobalt(II)]-µ-5-nitrobenzene-1,3-
dicarboxylato-
κ3O:
O',
O''] 0.25-hydrate]
top
Crystal data top
[Co(C8H3NO6)(C10H8N2)(H2O)]·0.25H2O | F(000) = 1820 |
Mr = 446.75 | Dx = 1.650 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3310 reflections |
a = 10.0561 (2) Å | θ = 2.5–23.3° |
b = 23.3986 (5) Å | µ = 1.01 mm−1 |
c = 15.3811 (3) Å | T = 293 K |
β = 96.317 (1)° | Block, red |
V = 3597.18 (13) Å3 | 0.26 × 0.14 × 0.12 mm |
Z = 8 | |
Data collection top
Bruker APEX area-detector diffractometer | 7054 independent reflections |
Radiation source: fine-focus sealed tube | 4747 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
φ and ω scans | θmax = 26.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −12→12 |
Tmin = 0.780, Tmax = 0.889 | k = −25→28 |
28059 measured reflections | l = −18→18 |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0675P)2] where P = (Fo2 + 2Fc2)/3 |
7054 reflections | (Δ/σ)max = 0.001 |
548 parameters | Δρmax = 0.66 e Å−3 |
6 restraints | Δρmin = −0.61 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 | Occ. (<1) |
Co1 | 0.65887 (4) | 0.153602 (15) | 0.35708 (2) | 0.02924 (12) | |
Co2 | 0.62890 (4) | 0.354806 (15) | 0.43390 (3) | 0.03239 (12) | |
C1 | 0.7020 (4) | 0.06948 (14) | 0.5082 (2) | 0.0527 (9) | |
H1 | 0.7224 | 0.1018 | 0.5423 | 0.063* | |
C2 | 0.7087 (4) | 0.01718 (16) | 0.5480 (2) | 0.0678 (11) | |
H2 | 0.7335 | 0.0141 | 0.6079 | 0.081* | |
C3 | 0.6786 (4) | −0.03087 (16) | 0.4984 (3) | 0.0700 (12) | |
H3 | 0.6802 | −0.0668 | 0.5242 | 0.084* | |
C4 | 0.6459 (4) | −0.02471 (14) | 0.4099 (2) | 0.0538 (9) | |
H4 | 0.6275 | −0.0567 | 0.3748 | 0.065* | |
C5 | 0.6405 (3) | 0.02927 (12) | 0.37304 (19) | 0.0343 (7) | |
C6 | 0.6087 (3) | 0.03962 (11) | 0.27789 (18) | 0.0316 (6) | |
C7 | 0.5816 (3) | −0.00290 (13) | 0.2168 (2) | 0.0422 (7) | |
H7 | 0.5813 | −0.0409 | 0.2343 | 0.051* | |
C8 | 0.5548 (3) | 0.01093 (14) | 0.1299 (2) | 0.0470 (8) | |
H8 | 0.5365 | −0.0176 | 0.0882 | 0.056* | |
C9 | 0.5554 (3) | 0.06725 (14) | 0.1055 (2) | 0.0453 (8) | |
H9 | 0.5369 | 0.0777 | 0.0471 | 0.054* | |
C10 | 0.5840 (3) | 0.10791 (13) | 0.16926 (19) | 0.0390 (7) | |
H10 | 0.5846 | 0.1461 | 0.1526 | 0.047* | |
C11 | 1.0118 (3) | 0.21754 (12) | 0.29309 (18) | 0.0319 (6) | |
C12 | 1.1301 (3) | 0.18902 (12) | 0.32003 (18) | 0.0318 (6) | |
H12 | 1.1264 | 0.1539 | 0.3480 | 0.038* | |
C13 | 1.2541 (3) | 0.21149 (11) | 0.30630 (17) | 0.0285 (6) | |
C14 | 1.2594 (3) | 0.26387 (12) | 0.26557 (18) | 0.0330 (6) | |
H14 | 1.3410 | 0.2797 | 0.2552 | 0.040* | |
C15 | 1.1410 (3) | 0.29225 (12) | 0.24055 (18) | 0.0358 (7) | |
C16 | 1.0170 (3) | 0.27030 (12) | 0.25225 (19) | 0.0371 (7) | |
H16 | 0.9391 | 0.2902 | 0.2334 | 0.044* | |
C17 | 0.8789 (3) | 0.19303 (14) | 0.3113 (2) | 0.0395 (7) | |
C18 | 1.3804 (3) | 0.17889 (12) | 0.33731 (18) | 0.0352 (7) | |
C19 | 0.5849 (3) | 0.44158 (14) | 0.2858 (2) | 0.0445 (8) | |
H19 | 0.5721 | 0.4097 | 0.2498 | 0.053* | |
C20 | 0.5692 (3) | 0.49524 (15) | 0.2487 (2) | 0.0533 (9) | |
H20 | 0.5460 | 0.4996 | 0.1889 | 0.064* | |
C21 | 0.5887 (3) | 0.54226 (15) | 0.3028 (3) | 0.0550 (9) | |
H21 | 0.5801 | 0.5789 | 0.2794 | 0.066* | |
C22 | 0.6208 (3) | 0.53500 (13) | 0.3910 (3) | 0.0470 (8) | |
H22 | 0.6320 | 0.5665 | 0.4279 | 0.056* | |
C23 | 0.6366 (3) | 0.47997 (12) | 0.4248 (2) | 0.0364 (7) | |
C24 | 0.6727 (3) | 0.46774 (12) | 0.5185 (2) | 0.0359 (7) | |
C25 | 0.7013 (3) | 0.50932 (13) | 0.5822 (2) | 0.0474 (8) | |
H25 | 0.6980 | 0.5478 | 0.5671 | 0.057* | |
C26 | 0.7347 (3) | 0.49318 (15) | 0.6676 (2) | 0.0531 (9) | |
H26 | 0.7532 | 0.5207 | 0.7109 | 0.064* | |
C27 | 0.7403 (3) | 0.43628 (16) | 0.6886 (2) | 0.0531 (9) | |
H27 | 0.7649 | 0.4245 | 0.7459 | 0.064* | |
C28 | 0.7088 (3) | 0.39677 (14) | 0.6229 (2) | 0.0461 (8) | |
H28 | 0.7106 | 0.3581 | 0.6373 | 0.055* | |
C29 | 0.2774 (3) | 0.29044 (11) | 0.49980 (18) | 0.0310 (6) | |
C30 | 0.2705 (3) | 0.24022 (12) | 0.54744 (18) | 0.0346 (7) | |
H30 | 0.3476 | 0.2210 | 0.5698 | 0.042* | |
C31 | 0.1459 (3) | 0.22001 (12) | 0.56031 (18) | 0.0347 (7) | |
C32 | 0.0282 (3) | 0.24754 (12) | 0.53001 (17) | 0.0331 (6) | |
H32 | −0.0541 | 0.2327 | 0.5410 | 0.040* | |
C33 | 0.0354 (3) | 0.29757 (12) | 0.48308 (17) | 0.0300 (6) | |
C34 | 0.1606 (3) | 0.31852 (11) | 0.46793 (17) | 0.0302 (6) | |
H34 | 0.1659 | 0.3520 | 0.4358 | 0.036* | |
C35 | 0.4107 (3) | 0.31407 (13) | 0.4814 (2) | 0.0362 (7) | |
C36 | −0.0897 (3) | 0.32995 (13) | 0.44861 (19) | 0.0353 (7) | |
N1 | 0.6671 (2) | 0.07613 (9) | 0.42224 (15) | 0.0337 (5) | |
N2 | 0.6111 (2) | 0.09513 (9) | 0.25411 (15) | 0.0316 (5) | |
N3 | 1.1478 (3) | 0.34977 (13) | 0.2030 (2) | 0.0618 (9) | |
N4 | 0.6181 (2) | 0.43378 (10) | 0.37187 (16) | 0.0369 (6) | |
N5 | 0.6757 (2) | 0.41175 (10) | 0.53952 (16) | 0.0361 (6) | |
N6 | 0.1367 (3) | 0.16614 (12) | 0.60850 (18) | 0.0498 (7) | |
O1 | 0.7737 (2) | 0.21915 (10) | 0.28538 (16) | 0.0541 (6) | |
O2 | 0.8765 (2) | 0.14792 (10) | 0.35358 (17) | 0.0561 (6) | |
O3 | 1.3720 (2) | 0.13325 (11) | 0.37447 (18) | 0.0707 (8) | |
O4 | 1.49045 (19) | 0.20084 (8) | 0.32076 (14) | 0.0401 (5) | |
O5 | 1.2547 (3) | 0.37396 (11) | 0.2080 (2) | 0.0796 (9) | |
O6 | 1.0470 (3) | 0.37006 (15) | 0.1666 (3) | 0.1368 (18) | |
O7 | 0.5160 (2) | 0.28810 (10) | 0.50841 (15) | 0.0488 (6) | |
O8 | 0.4136 (2) | 0.35911 (9) | 0.43859 (16) | 0.0533 (6) | |
O9 | −0.0802 (2) | 0.37362 (10) | 0.40642 (16) | 0.0586 (7) | |
O10 | −0.20023 (19) | 0.30934 (8) | 0.46820 (14) | 0.0431 (5) | |
O11 | 0.0280 (3) | 0.14338 (12) | 0.6070 (2) | 0.0878 (10) | |
O12 | 0.2385 (3) | 0.14727 (10) | 0.64922 (17) | 0.0654 (7) | |
O13W | 0.6886 (2) | 0.20216 (8) | 0.47511 (14) | 0.0398 (5) | |
H13A | 0.621 (2) | 0.2172 (12) | 0.495 (2) | 0.063 (12)* | |
H13B | 0.747 (3) | 0.2280 (11) | 0.471 (3) | 0.093 (16)* | |
O14W | 0.6001 (2) | 0.30670 (9) | 0.31691 (14) | 0.0391 (5) | |
H14B | 0.6720 (18) | 0.2941 (12) | 0.301 (2) | 0.062 (12)* | |
H14C | 0.544 (2) | 0.2797 (10) | 0.319 (3) | 0.085 (15)* | |
O15W | 0.4785 (15) | 0.5576 (5) | 0.0575 (8) | 0.258 (7) | 0.50 |
H15A | 0.5065 | 0.5908 | 0.0453 | 0.309* | 0.50 |
H15B | 0.4874 | 0.5277 | 0.0274 | 0.309* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co1 | 0.0255 (2) | 0.0231 (2) | 0.0390 (2) | 0.00154 (15) | 0.00267 (15) | 0.00216 (15) |
Co2 | 0.0244 (2) | 0.0243 (2) | 0.0490 (3) | 0.00098 (15) | 0.00640 (17) | 0.00129 (16) |
C1 | 0.072 (3) | 0.047 (2) | 0.0386 (19) | 0.0042 (17) | 0.0033 (16) | 0.0036 (15) |
C2 | 0.102 (3) | 0.057 (2) | 0.044 (2) | 0.012 (2) | 0.005 (2) | 0.0197 (18) |
C3 | 0.101 (4) | 0.043 (2) | 0.065 (3) | −0.001 (2) | 0.009 (2) | 0.0256 (19) |
C4 | 0.069 (3) | 0.0292 (17) | 0.064 (2) | −0.0015 (16) | 0.0075 (18) | 0.0094 (15) |
C5 | 0.0307 (17) | 0.0273 (15) | 0.0455 (18) | −0.0017 (12) | 0.0066 (13) | 0.0054 (13) |
C6 | 0.0215 (15) | 0.0295 (15) | 0.0439 (17) | −0.0003 (11) | 0.0039 (12) | 0.0003 (12) |
C7 | 0.0375 (19) | 0.0285 (16) | 0.060 (2) | −0.0027 (13) | 0.0045 (15) | −0.0038 (14) |
C8 | 0.038 (2) | 0.049 (2) | 0.053 (2) | −0.0032 (15) | −0.0014 (15) | −0.0153 (16) |
C9 | 0.045 (2) | 0.052 (2) | 0.0385 (18) | 0.0043 (15) | −0.0003 (14) | −0.0033 (15) |
C10 | 0.0414 (19) | 0.0370 (17) | 0.0384 (17) | 0.0046 (14) | 0.0028 (13) | 0.0024 (13) |
C11 | 0.0213 (15) | 0.0366 (16) | 0.0380 (16) | −0.0003 (12) | 0.0042 (12) | −0.0087 (12) |
C12 | 0.0282 (17) | 0.0279 (15) | 0.0401 (15) | −0.0012 (12) | 0.0068 (12) | −0.0017 (12) |
C13 | 0.0231 (16) | 0.0290 (15) | 0.0332 (15) | 0.0027 (11) | 0.0023 (11) | 0.0001 (11) |
C14 | 0.0218 (15) | 0.0384 (16) | 0.0391 (16) | −0.0016 (12) | 0.0047 (12) | 0.0044 (12) |
C15 | 0.0345 (18) | 0.0354 (16) | 0.0385 (16) | 0.0062 (13) | 0.0081 (13) | 0.0120 (12) |
C16 | 0.0247 (17) | 0.0455 (18) | 0.0409 (17) | 0.0082 (13) | 0.0032 (12) | 0.0021 (13) |
C17 | 0.0259 (18) | 0.0458 (19) | 0.0480 (18) | −0.0021 (14) | 0.0089 (14) | −0.0177 (15) |
C18 | 0.0272 (18) | 0.0370 (17) | 0.0414 (17) | 0.0057 (13) | 0.0035 (12) | 0.0009 (13) |
C19 | 0.040 (2) | 0.0445 (19) | 0.050 (2) | 0.0031 (14) | 0.0095 (15) | 0.0041 (15) |
C20 | 0.045 (2) | 0.058 (2) | 0.059 (2) | 0.0100 (17) | 0.0131 (17) | 0.0207 (18) |
C21 | 0.042 (2) | 0.041 (2) | 0.084 (3) | 0.0058 (15) | 0.0181 (18) | 0.0218 (19) |
C22 | 0.0356 (19) | 0.0294 (17) | 0.077 (2) | 0.0001 (13) | 0.0130 (16) | 0.0071 (16) |
C23 | 0.0207 (16) | 0.0279 (15) | 0.063 (2) | −0.0015 (12) | 0.0135 (14) | 0.0023 (14) |
C24 | 0.0247 (16) | 0.0302 (16) | 0.0541 (19) | 0.0013 (12) | 0.0106 (13) | −0.0038 (13) |
C25 | 0.0341 (19) | 0.0344 (18) | 0.075 (2) | −0.0023 (14) | 0.0119 (16) | −0.0063 (16) |
C26 | 0.040 (2) | 0.057 (2) | 0.062 (2) | −0.0048 (16) | 0.0044 (17) | −0.0186 (18) |
C27 | 0.045 (2) | 0.064 (2) | 0.050 (2) | 0.0031 (17) | 0.0039 (16) | −0.0061 (17) |
C28 | 0.041 (2) | 0.0436 (19) | 0.054 (2) | 0.0060 (15) | 0.0073 (15) | 0.0027 (16) |
C29 | 0.0277 (17) | 0.0297 (15) | 0.0362 (15) | −0.0018 (12) | 0.0060 (12) | −0.0059 (12) |
C30 | 0.0271 (16) | 0.0406 (17) | 0.0350 (16) | 0.0028 (13) | −0.0010 (12) | −0.0006 (13) |
C31 | 0.0316 (18) | 0.0352 (16) | 0.0369 (16) | −0.0020 (13) | 0.0017 (12) | 0.0055 (12) |
C32 | 0.0238 (16) | 0.0398 (17) | 0.0359 (16) | −0.0050 (12) | 0.0044 (12) | −0.0007 (13) |
C33 | 0.0237 (16) | 0.0336 (16) | 0.0326 (15) | 0.0015 (11) | 0.0021 (11) | −0.0058 (12) |
C34 | 0.0257 (16) | 0.0284 (15) | 0.0370 (15) | −0.0020 (12) | 0.0056 (12) | 0.0007 (12) |
C35 | 0.0264 (18) | 0.0354 (17) | 0.0484 (18) | −0.0014 (13) | 0.0115 (13) | −0.0134 (14) |
C36 | 0.0272 (17) | 0.0340 (16) | 0.0439 (17) | 0.0016 (13) | 0.0001 (13) | −0.0073 (13) |
N1 | 0.0353 (14) | 0.0289 (13) | 0.0369 (14) | 0.0002 (10) | 0.0031 (11) | 0.0054 (10) |
N2 | 0.0286 (13) | 0.0273 (12) | 0.0392 (14) | 0.0005 (10) | 0.0046 (10) | 0.0011 (10) |
N3 | 0.052 (2) | 0.056 (2) | 0.080 (2) | 0.0173 (16) | 0.0184 (17) | 0.0356 (16) |
N4 | 0.0276 (14) | 0.0301 (13) | 0.0543 (17) | 0.0010 (10) | 0.0110 (12) | 0.0026 (11) |
N5 | 0.0278 (14) | 0.0320 (13) | 0.0495 (15) | 0.0038 (10) | 0.0083 (11) | 0.0004 (11) |
N6 | 0.0467 (19) | 0.0463 (16) | 0.0558 (18) | −0.0004 (14) | 0.0033 (14) | 0.0151 (13) |
O1 | 0.0247 (13) | 0.0592 (15) | 0.0793 (17) | 0.0027 (11) | 0.0097 (11) | −0.0089 (12) |
O2 | 0.0376 (14) | 0.0508 (15) | 0.0813 (17) | −0.0096 (11) | 0.0134 (12) | 0.0055 (13) |
O3 | 0.0441 (15) | 0.0650 (17) | 0.105 (2) | 0.0145 (12) | 0.0169 (14) | 0.0536 (16) |
O4 | 0.0211 (11) | 0.0313 (11) | 0.0671 (14) | 0.0009 (8) | 0.0015 (9) | −0.0015 (10) |
O5 | 0.074 (2) | 0.0534 (16) | 0.109 (2) | −0.0129 (15) | 0.0007 (17) | 0.0357 (16) |
O6 | 0.055 (2) | 0.127 (3) | 0.233 (4) | 0.043 (2) | 0.039 (2) | 0.133 (3) |
O7 | 0.0225 (12) | 0.0525 (13) | 0.0724 (15) | 0.0025 (10) | 0.0094 (10) | −0.0057 (11) |
O8 | 0.0369 (14) | 0.0385 (13) | 0.0870 (17) | −0.0075 (10) | 0.0183 (12) | 0.0072 (12) |
O9 | 0.0416 (15) | 0.0537 (15) | 0.0801 (17) | 0.0100 (11) | 0.0048 (12) | 0.0261 (13) |
O10 | 0.0200 (11) | 0.0351 (11) | 0.0736 (15) | 0.0007 (9) | 0.0026 (10) | −0.0045 (10) |
O11 | 0.0584 (19) | 0.086 (2) | 0.113 (2) | −0.0310 (16) | −0.0175 (16) | 0.0569 (18) |
O12 | 0.0494 (16) | 0.0577 (16) | 0.0891 (19) | 0.0149 (12) | 0.0072 (14) | 0.0323 (14) |
O13W | 0.0369 (14) | 0.0308 (11) | 0.0510 (13) | 0.0044 (10) | 0.0015 (10) | −0.0042 (9) |
O14W | 0.0332 (13) | 0.0316 (12) | 0.0524 (13) | 0.0035 (10) | 0.0041 (10) | 0.0002 (10) |
O15W | 0.33 (2) | 0.200 (12) | 0.232 (14) | −0.085 (12) | −0.008 (12) | −0.008 (10) |
Geometric parameters (Å, º) top
Co1—N1 | 2.069 (2) | C19—N4 | 1.341 (4) |
Co1—N2 | 2.108 (2) | C19—C20 | 1.381 (4) |
Co1—O1 | 2.276 (2) | C19—H19 | 0.9300 |
Co1—O2 | 2.199 (2) | C20—C21 | 1.380 (5) |
Co1—O4i | 2.048 (2) | C20—H20 | 0.9300 |
Co1—O13W | 2.135 (2) | C21—C22 | 1.370 (5) |
Co2—N4 | 2.077 (2) | C21—H21 | 0.9300 |
Co2—N5 | 2.114 (2) | C22—C23 | 1.391 (4) |
Co2—O7 | 2.307 (2) | C22—H22 | 0.9300 |
Co2—O8 | 2.176 (2) | C23—N4 | 1.354 (4) |
Co2—O10ii | 2.040 (2) | C23—C24 | 1.476 (4) |
Co2—O14W | 2.115 (2) | C24—N5 | 1.349 (3) |
C1—N1 | 1.340 (4) | C24—C25 | 1.388 (4) |
C1—C2 | 1.366 (5) | C25—C26 | 1.372 (5) |
C1—H1 | 0.9300 | C25—H25 | 0.9300 |
C2—C3 | 1.374 (5) | C26—C27 | 1.370 (5) |
C2—H2 | 0.9300 | C26—H26 | 0.9300 |
C3—C4 | 1.371 (5) | C27—C28 | 1.381 (4) |
C3—H3 | 0.9300 | C27—H27 | 0.9300 |
C4—C5 | 1.383 (4) | C28—N5 | 1.336 (4) |
C4—H4 | 0.9300 | C28—H28 | 0.9300 |
C5—N1 | 1.342 (3) | C29—C34 | 1.387 (4) |
C5—C6 | 1.483 (4) | C29—C30 | 1.391 (4) |
C6—N2 | 1.350 (3) | C29—C35 | 1.506 (4) |
C6—C7 | 1.375 (4) | C30—C31 | 1.373 (4) |
C7—C8 | 1.372 (4) | C30—H30 | 0.9300 |
C7—H7 | 0.9300 | C31—C32 | 1.383 (4) |
C8—C9 | 1.371 (4) | C31—N6 | 1.470 (4) |
C8—H8 | 0.9300 | C32—C33 | 1.382 (4) |
C9—C10 | 1.373 (4) | C32—H32 | 0.9300 |
C9—H9 | 0.9300 | C33—C34 | 1.394 (4) |
C10—N2 | 1.337 (3) | C33—C36 | 1.514 (4) |
C10—H10 | 0.9300 | C34—H34 | 0.9300 |
C11—C12 | 1.387 (4) | C35—O8 | 1.245 (4) |
C11—C16 | 1.389 (4) | C35—O7 | 1.251 (4) |
C11—C17 | 1.509 (4) | C36—O9 | 1.220 (4) |
C12—C13 | 1.390 (4) | C36—O10 | 1.278 (3) |
C12—H12 | 0.9300 | N3—O6 | 1.201 (4) |
C13—C14 | 1.380 (4) | N3—O5 | 1.210 (4) |
C13—C18 | 1.513 (4) | N6—O11 | 1.214 (4) |
C14—C15 | 1.380 (4) | N6—O12 | 1.222 (3) |
C14—H14 | 0.9300 | O4—Co1ii | 2.0480 (19) |
C15—C16 | 1.379 (4) | O10—Co2i | 2.040 (2) |
C15—N3 | 1.469 (4) | O13W—H13A | 0.853 (10) |
C16—H16 | 0.9300 | O13W—H13B | 0.850 (10) |
C17—O2 | 1.241 (4) | O14W—H14B | 0.842 (10) |
C17—O1 | 1.249 (4) | O14W—H14C | 0.849 (10) |
C18—O3 | 1.218 (3) | O15W—H15A | 0.8556 |
C18—O4 | 1.271 (3) | O15W—H15B | 0.8498 |
| | | |
N1—Co1—N2 | 77.82 (9) | N4—C19—H19 | 118.8 |
N1—Co1—O1 | 146.07 (9) | C20—C19—H19 | 118.8 |
N1—Co1—O2 | 88.38 (9) | C21—C20—C19 | 118.3 (3) |
N1—Co1—O13W | 93.44 (8) | C21—C20—H20 | 120.9 |
N2—Co1—O1 | 99.16 (9) | C19—C20—H20 | 120.9 |
N2—Co1—O2 | 95.02 (9) | C22—C21—C20 | 120.0 (3) |
N2—Co1—O13W | 169.57 (9) | C22—C21—H21 | 120.0 |
O2—Co1—O1 | 57.98 (8) | C20—C21—H21 | 120.0 |
O4i—Co1—N1 | 126.38 (9) | C21—C22—C23 | 119.3 (3) |
O4i—Co1—N2 | 91.83 (8) | C21—C22—H22 | 120.3 |
O4i—Co1—O1 | 87.27 (8) | C23—C22—H22 | 120.3 |
O4i—Co1—O2 | 145.22 (9) | N4—C23—C22 | 120.8 (3) |
O4i—Co1—O13W | 88.80 (8) | N4—C23—C24 | 115.8 (2) |
O13W—Co1—O1 | 91.28 (9) | C22—C23—C24 | 123.4 (3) |
O13W—Co1—O2 | 90.36 (9) | N5—C24—C25 | 121.0 (3) |
N4—Co2—N5 | 77.77 (9) | N5—C24—C23 | 114.8 (2) |
N4—Co2—O8 | 88.41 (9) | C25—C24—C23 | 124.3 (3) |
N4—Co2—O14W | 95.01 (9) | C26—C25—C24 | 119.5 (3) |
N4—Co2—O7 | 145.72 (9) | C26—C25—H25 | 120.3 |
N5—Co2—O7 | 97.17 (9) | C24—C25—H25 | 120.3 |
N5—Co2—O8 | 94.80 (9) | C27—C26—C25 | 119.5 (3) |
N5—Co2—O14W | 170.88 (9) | C27—C26—H26 | 120.2 |
O8—Co2—O7 | 57.94 (8) | C25—C26—H26 | 120.2 |
O10ii—Co2—N4 | 125.63 (9) | C26—C27—C28 | 118.5 (3) |
O10ii—Co2—N5 | 91.14 (9) | C26—C27—H27 | 120.7 |
O10ii—Co2—O7 | 88.01 (8) | C28—C27—H27 | 120.7 |
O10ii—Co2—O8 | 145.90 (8) | N5—C28—C27 | 122.7 (3) |
O10ii—Co2—O14W | 88.58 (8) | N5—C28—H28 | 118.7 |
O14W—Co2—O7 | 91.93 (8) | C27—C28—H28 | 118.7 |
O14W—Co2—O8 | 90.52 (9) | C34—C29—C30 | 119.8 (3) |
N1—C1—C2 | 122.7 (3) | C34—C29—C35 | 119.8 (3) |
N1—C1—H1 | 118.6 | C30—C29—C35 | 120.4 (3) |
C2—C1—H1 | 118.6 | C31—C30—C29 | 117.8 (3) |
C1—C2—C3 | 119.1 (3) | C31—C30—H30 | 121.1 |
C1—C2—H2 | 120.4 | C29—C30—H30 | 121.1 |
C3—C2—H2 | 120.4 | C30—C31—C32 | 123.5 (3) |
C4—C3—C2 | 118.6 (3) | C30—C31—N6 | 118.5 (3) |
C4—C3—H3 | 120.7 | C32—C31—N6 | 118.1 (3) |
C2—C3—H3 | 120.7 | C33—C32—C31 | 118.6 (3) |
C3—C4—C5 | 119.8 (3) | C33—C32—H32 | 120.7 |
C3—C4—H4 | 120.1 | C31—C32—H32 | 120.7 |
C5—C4—H4 | 120.1 | C32—C33—C34 | 119.1 (3) |
N1—C5—C4 | 121.2 (3) | C32—C33—C36 | 121.2 (3) |
N1—C5—C6 | 115.5 (2) | C34—C33—C36 | 119.8 (3) |
C4—C5—C6 | 123.2 (3) | C29—C34—C33 | 121.3 (3) |
N2—C6—C7 | 121.3 (3) | C29—C34—H34 | 119.4 |
N2—C6—C5 | 114.6 (2) | C33—C34—H34 | 119.4 |
C7—C6—C5 | 124.1 (3) | O8—C35—O7 | 121.2 (3) |
C8—C7—C6 | 119.8 (3) | O8—C35—C29 | 118.9 (3) |
C8—C7—H7 | 120.1 | O7—C35—C29 | 119.8 (3) |
C6—C7—H7 | 120.1 | O9—C36—O10 | 124.2 (3) |
C9—C8—C7 | 119.2 (3) | O9—C36—C33 | 119.7 (3) |
C9—C8—H8 | 120.4 | O10—C36—C33 | 116.1 (3) |
C7—C8—H8 | 120.4 | C1—N1—C5 | 118.4 (3) |
C8—C9—C10 | 118.5 (3) | C1—N1—Co1 | 124.9 (2) |
C8—C9—H9 | 120.7 | C5—N1—Co1 | 116.60 (18) |
C10—C9—H9 | 120.7 | C10—N2—C6 | 118.1 (2) |
N2—C10—C9 | 123.1 (3) | C10—N2—Co1 | 126.38 (19) |
N2—C10—H10 | 118.5 | C6—N2—Co1 | 115.48 (18) |
C9—C10—H10 | 118.5 | O6—N3—O5 | 122.9 (3) |
C12—C11—C16 | 119.3 (3) | O6—N3—C15 | 118.2 (3) |
C12—C11—C17 | 120.6 (3) | O5—N3—C15 | 118.9 (3) |
C16—C11—C17 | 120.0 (3) | C19—N4—C23 | 119.2 (3) |
C11—C12—C13 | 121.8 (3) | C19—N4—Co2 | 124.7 (2) |
C11—C12—H12 | 119.1 | C23—N4—Co2 | 115.93 (19) |
C13—C12—H12 | 119.1 | C28—N5—C24 | 118.8 (3) |
C14—C13—C12 | 119.0 (2) | C28—N5—Co2 | 125.7 (2) |
C14—C13—C18 | 121.2 (2) | C24—N5—Co2 | 115.54 (19) |
C12—C13—C18 | 119.8 (2) | O11—N6—O12 | 123.6 (3) |
C13—C14—C15 | 118.6 (3) | O11—N6—C31 | 118.2 (3) |
C13—C14—H14 | 120.7 | O12—N6—C31 | 118.2 (3) |
C15—C14—H14 | 120.7 | C17—O1—Co1 | 88.4 (2) |
C16—C15—C14 | 123.3 (3) | C17—O2—Co1 | 92.18 (19) |
C16—C15—N3 | 118.3 (3) | C18—O4—Co1ii | 116.08 (18) |
C14—C15—N3 | 118.3 (3) | C35—O7—Co2 | 87.20 (19) |
C15—C16—C11 | 118.0 (3) | C35—O8—Co2 | 93.42 (18) |
C15—C16—H16 | 121.0 | C36—O10—Co2i | 118.16 (19) |
C11—C16—H16 | 121.0 | Co1—O13W—H13A | 118 (2) |
O2—C17—O1 | 121.3 (3) | Co1—O13W—H13B | 110 (3) |
O2—C17—C11 | 119.3 (3) | H13A—O13W—H13B | 108.9 (16) |
O1—C17—C11 | 119.4 (3) | Co2—O14W—H14B | 113 (2) |
O3—C18—O4 | 123.7 (3) | Co2—O14W—H14C | 113 (3) |
O3—C18—C13 | 119.4 (3) | H14B—O14W—H14C | 110.1 (17) |
O4—C18—C13 | 116.9 (2) | H15A—O15W—H15B | 124.9 |
N4—C19—C20 | 122.4 (3) | | |
| | | |
N1—C1—C2—C3 | −0.1 (6) | C9—C10—N2—Co1 | 179.1 (2) |
C1—C2—C3—C4 | 1.7 (6) | C7—C6—N2—C10 | 1.1 (4) |
C2—C3—C4—C5 | −1.7 (6) | C5—C6—N2—C10 | 179.8 (2) |
C3—C4—C5—N1 | 0.3 (5) | C7—C6—N2—Co1 | −178.7 (2) |
C3—C4—C5—C6 | 178.7 (3) | C5—C6—N2—Co1 | 0.0 (3) |
N1—C5—C6—N2 | −0.1 (4) | O4i—Co1—N2—C10 | 53.4 (2) |
C4—C5—C6—N2 | −178.6 (3) | N1—Co1—N2—C10 | −179.7 (2) |
N1—C5—C6—C7 | 178.6 (3) | O13W—Co1—N2—C10 | 146.8 (4) |
C4—C5—C6—C7 | 0.0 (5) | O2—Co1—N2—C10 | −92.4 (2) |
N2—C6—C7—C8 | −0.7 (4) | O1—Co1—N2—C10 | −34.1 (2) |
C5—C6—C7—C8 | −179.2 (3) | O4i—Co1—N2—C6 | −126.81 (19) |
C6—C7—C8—C9 | −0.1 (5) | N1—Co1—N2—C6 | 0.07 (19) |
C7—C8—C9—C10 | 0.5 (5) | O13W—Co1—N2—C6 | −33.5 (6) |
C8—C9—C10—N2 | −0.1 (5) | O2—Co1—N2—C6 | 87.3 (2) |
C16—C11—C12—C13 | −0.8 (4) | O1—Co1—N2—C6 | 145.66 (19) |
C17—C11—C12—C13 | −178.1 (2) | C16—C15—N3—O6 | −16.2 (5) |
C11—C12—C13—C14 | 0.7 (4) | C14—C15—N3—O6 | 166.4 (4) |
C11—C12—C13—C18 | 179.7 (2) | C16—C15—N3—O5 | 165.7 (3) |
C12—C13—C14—C15 | 0.5 (4) | C14—C15—N3—O5 | −11.7 (5) |
C18—C13—C14—C15 | −178.5 (3) | C20—C19—N4—C23 | 0.2 (4) |
C13—C14—C15—C16 | −1.6 (4) | C20—C19—N4—Co2 | 174.9 (2) |
C13—C14—C15—N3 | 175.6 (3) | C22—C23—N4—C19 | 0.3 (4) |
C14—C15—C16—C11 | 1.5 (4) | C24—C23—N4—C19 | 179.9 (3) |
N3—C15—C16—C11 | −175.8 (3) | C22—C23—N4—Co2 | −174.8 (2) |
C12—C11—C16—C15 | −0.3 (4) | C24—C23—N4—Co2 | 4.8 (3) |
C17—C11—C16—C15 | 177.0 (3) | O10ii—Co2—N4—C19 | 99.1 (2) |
C12—C11—C17—O2 | 2.6 (4) | N5—Co2—N4—C19 | −178.4 (2) |
C16—C11—C17—O2 | −174.7 (3) | O14W—Co2—N4—C19 | 7.3 (2) |
C12—C11—C17—O1 | −179.1 (3) | O8—Co2—N4—C19 | −83.1 (2) |
C16—C11—C17—O1 | 3.7 (4) | O7—Co2—N4—C19 | −93.6 (3) |
C14—C13—C18—O3 | 178.7 (3) | O10ii—Co2—N4—C23 | −86.1 (2) |
C12—C13—C18—O3 | −0.3 (4) | N5—Co2—N4—C23 | −3.61 (19) |
C14—C13—C18—O4 | −2.9 (4) | O14W—Co2—N4—C23 | −177.96 (19) |
C12—C13—C18—O4 | 178.1 (2) | O8—Co2—N4—C23 | 91.7 (2) |
N4—C19—C20—C21 | 0.1 (5) | O7—Co2—N4—C23 | 81.2 (2) |
C19—C20—C21—C22 | −1.0 (5) | C27—C28—N5—C24 | −0.1 (4) |
C20—C21—C22—C23 | 1.5 (5) | C27—C28—N5—Co2 | 179.0 (2) |
C21—C22—C23—N4 | −1.2 (4) | C25—C24—N5—C28 | −0.9 (4) |
C21—C22—C23—C24 | 179.2 (3) | C23—C24—N5—C28 | 179.4 (2) |
N4—C23—C24—N5 | −3.3 (4) | C25—C24—N5—Co2 | 179.9 (2) |
C22—C23—C24—N5 | 176.3 (3) | C23—C24—N5—Co2 | 0.2 (3) |
N4—C23—C24—C25 | 177.0 (3) | O10ii—Co2—N5—C28 | −51.1 (2) |
C22—C23—C24—C25 | −3.3 (4) | N4—Co2—N5—C28 | −177.4 (3) |
N5—C24—C25—C26 | 0.7 (5) | O8—Co2—N5—C28 | 95.3 (2) |
C23—C24—C25—C26 | −179.6 (3) | O7—Co2—N5—C28 | 37.1 (2) |
C24—C25—C26—C27 | 0.6 (5) | O10ii—Co2—N5—C24 | 128.0 (2) |
C25—C26—C27—C28 | −1.6 (5) | N4—Co2—N5—C24 | 1.76 (19) |
C26—C27—C28—N5 | 1.4 (5) | O8—Co2—N5—C24 | −85.6 (2) |
C34—C29—C30—C31 | 0.6 (4) | O7—Co2—N5—C24 | −143.82 (19) |
C35—C29—C30—C31 | −178.4 (2) | C30—C31—N6—O11 | −167.6 (3) |
C29—C30—C31—C32 | −1.4 (4) | C32—C31—N6—O11 | 12.1 (5) |
C29—C30—C31—N6 | 178.4 (3) | C30—C31—N6—O12 | 13.7 (4) |
C30—C31—C32—C33 | 1.1 (4) | C32—C31—N6—O12 | −166.5 (3) |
N6—C31—C32—C33 | −178.7 (2) | O2—C17—O1—Co1 | 3.9 (3) |
C31—C32—C33—C34 | 0.0 (4) | C11—C17—O1—Co1 | −174.4 (2) |
C31—C32—C33—C36 | −179.6 (3) | O4i—Co1—O1—C17 | 176.15 (18) |
C30—C29—C34—C33 | 0.4 (4) | N1—Co1—O1—C17 | −10.7 (3) |
C35—C29—C34—C33 | 179.4 (2) | N2—Co1—O1—C17 | −92.43 (18) |
C32—C33—C34—C29 | −0.7 (4) | O13W—Co1—O1—C17 | 87.41 (18) |
C36—C33—C34—C29 | 178.9 (2) | O2—Co1—O1—C17 | −2.21 (17) |
C34—C29—C35—O8 | 1.0 (4) | O1—C17—O2—Co1 | −4.0 (3) |
C30—C29—C35—O8 | −180.0 (3) | C11—C17—O2—Co1 | 174.3 (2) |
C34—C29—C35—O7 | −178.4 (3) | O4i—Co1—O2—C17 | −0.6 (3) |
C30—C29—C35—O7 | 0.7 (4) | N1—Co1—O2—C17 | 177.52 (19) |
C32—C33—C36—O9 | −179.1 (3) | N2—Co1—O2—C17 | 99.90 (19) |
C34—C33—C36—O9 | 1.3 (4) | O13W—Co1—O2—C17 | −89.05 (19) |
C32—C33—C36—O10 | 2.4 (4) | O1—Co1—O2—C17 | 2.23 (17) |
C34—C33—C36—O10 | −177.2 (2) | O3—C18—O4—Co1ii | 1.8 (4) |
C2—C1—N1—C5 | −1.3 (5) | C13—C18—O4—Co1ii | −176.55 (18) |
C2—C1—N1—Co1 | −178.5 (3) | O8—C35—O7—Co2 | −4.4 (3) |
C4—C5—N1—C1 | 1.3 (5) | C29—C35—O7—Co2 | 175.0 (2) |
C6—C5—N1—C1 | −177.3 (3) | O10ii—Co2—O7—C35 | −175.39 (17) |
C4—C5—N1—Co1 | 178.7 (2) | N4—Co2—O7—C35 | 14.9 (3) |
C6—C5—N1—Co1 | 0.1 (3) | N5—Co2—O7—C35 | 93.71 (17) |
O4i—Co1—N1—C1 | −99.7 (3) | O14W—Co2—O7—C35 | −86.88 (17) |
N2—Co1—N1—C1 | 177.1 (3) | O8—Co2—O7—C35 | 2.53 (16) |
O13W—Co1—N1—C1 | −8.6 (3) | O7—C35—O8—Co2 | 4.6 (3) |
O2—Co1—N1—C1 | 81.6 (3) | C29—C35—O8—Co2 | −174.7 (2) |
O1—Co1—N1—C1 | 88.8 (3) | O10ii—Co2—O8—C35 | 1.2 (3) |
O4i—Co1—N1—C5 | 83.1 (2) | N4—Co2—O8—C35 | −175.59 (19) |
N2—Co1—N1—C5 | −0.1 (2) | N5—Co2—O8—C35 | −98.01 (19) |
O13W—Co1—N1—C5 | 174.1 (2) | O14W—Co2—O8—C35 | 89.41 (18) |
O2—Co1—N1—C5 | −95.6 (2) | O7—Co2—O8—C35 | −2.54 (17) |
O1—Co1—N1—C5 | −88.4 (2) | O9—C36—O10—Co2i | −4.2 (4) |
C9—C10—N2—C6 | −0.7 (4) | C33—C36—O10—Co2i | 174.28 (17) |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O13W—H13A···O7 | 0.85 (1) | 1.99 (2) | 2.741 (3) | 147 (3) |
O13W—H13B···O10ii | 0.85 (1) | 1.98 (2) | 2.753 (3) | 151 (3) |
O14W—H14B···O1 | 0.84 (1) | 2.06 (2) | 2.769 (3) | 142 (3) |
O14W—H14C···O4i | 0.85 (1) | 1.92 (2) | 2.715 (3) | 155 (3) |
O15W—H15A···O2iii | 0.86 | 2.28 | 2.833 (12) | 123 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+3/2, y+1/2, −z+1/2. |
π–π stacking interaction geometrical parameters (Å, °) topRings | Distence | Dihedral angle |
Cg1···Cg1i | 3.977 (2) | parallel |
Cg2···Cg4 | 3.583 (2) | 3.57 (5) |
Cg2···Cg5 | 3.889 (2) | 6.65 (5) |
Cg3···Cg6 | 3.662 (2) | 4.9 (1) |
Cg5···Cg4iv | 3.609 (2) | 3.08 (5) |
Notes: Cg1 is the centroid of the ring containing N1;
Cg1i is the centroid of the ring containing N1i;
Cg2 is the centroid of the ring containing N2:
Cg3 is the centroid of the ring containing C11;
Cg4 is the centroid of the ring containing N4ii;
Cg4iv is the centroid of the ring containing N4iv;
Cg5 is the centroid of the ring containing N5iii;
Cg6 is the centroid of the ring containing C29v.
Symmetry codes: (i) 1-x, -y, 1-z; (ii) -1/2+x, 1/2-y, -1/2+z;
(iii) 3/2-x, -1/2+y, 1/2-z; (iv) 1/2-x, -1/2+y, 1/2-z;
(v) 1+x, y, z. |