metal-organic compounds
The crystal structure of the title compound, {[Co2(C8H4NO2)4(C10H8N2)2]·2H2O·4C3H7NO}n, features a centrosymmetric eight-membered –Co—O—C—O—Co—O—C—O- ring that arises from the bridging of two Co atoms by two cyanobenzoate units across a center of symmetry. Each Co atom is also chelated by a cyanobenzoate unit and the two remaining coordination sites, trans to each other in the distorted octahedron, are occupied by the N atoms of the heterocycle, resulting in a polymeric ribbon structure. The water and dimethylformamide molecules occupy the space between the chains.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805001054/hb6139sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805001054/hb6139Isup2.hkl |
CCDC reference: 263555
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.007 Å
- R factor = 0.065
- wR factor = 0.188
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT220_ALERT_2_B Large Non-Solvent N Ueq(max)/Ueq(min) ... 3.51 Ratio
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.641 0.949 Tmin' and Tmax expected: 0.836 0.949 RR' = 0.766 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 .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.76 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C27 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C30 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N5 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N6 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C15 - C18 ... 1.46 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C23 - C26 ... 1.46 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 13 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 3 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 5 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: RAPID-AUTO (Rigaku, 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: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
catena-Poly[[[bis(µ-4-cyanobenzoato-κ2O:O)bis[(4-cyanobenzoato-
κ2O,O')cobalt(II)]]-di-µ-4,4'-bipyridine-κ4N:N'] dihydrate dimethylformamide tetrasolvate] top
Crystal data top
[Co2(C8H4NO2)4(C10H8N2)2]·2H2O·4C3H7NO | F(000) = 1396 |
Mr = 1343.14 | Dx = 1.378 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 29299 reflections |
a = 17.6227 (9) Å | θ = 1.2–27.5° |
b = 11.3661 (5) Å | µ = 0.59 mm−1 |
c = 17.1939 (7) Å | T = 173 K |
β = 110.011 (2)° | Needle, red |
V = 3236.0 (3) Å3 | 0.30 × 0.18 × 0.09 mm |
Z = 2 |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 5653 independent reflections |
Radiation source: fine-focus sealed tube | 4559 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
ω scans | θmax = 25.0°, θmin = 1.2° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −20→20 |
Tmin = 0.641, Tmax = 0.949 | k = −13→11 |
23077 measured reflections | l = −20→20 |
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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.188 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0939P)2 + 6.7732P] where P = (Fo2 + 2Fc2)/3 |
5653 reflections | (Δ/σ)max = 0.001 |
419 parameters | Δρmax = 1.06 e Å−3 |
0 restraints | Δρmin = −0.60 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Co1 | 0.43203 (3) | 0.53041 (4) | 0.37799 (3) | 0.0232 (2) | |
O1 | 0.5503 (2) | 0.5222 (2) | 0.3853 (2) | 0.0296 (6) | |
O2 | 0.5940 (2) | 0.4636 (3) | 0.5162 (2) | 0.0344 (7) | |
O3 | 0.3040 (2) | 0.5428 (3) | 0.3044 (2) | 0.0369 (7) | |
O4 | 0.3935 (2) | 0.5408 (3) | 0.2415 (2) | 0.0337 (7) | |
O5 | 0.1870 (3) | 0.9846 (6) | 0.3173 (4) | 0.099 (2) | |
O6 | 0.2909 (4) | 0.2142 (5) | 0.5336 (4) | 0.106 (2) | |
O1w | 0.173 (1) | 0.720 (2) | 0.3202 (11) | 0.318 (8) | |
N5 | 0.0881 (5) | 1.1194 (8) | 0.2967 (4) | 0.103 (3) | |
N6 | 0.2234 (2) | 0.2451 (4) | 0.6211 (3) | 0.044 (1) | |
N1 | 0.4290 (2) | 0.3434 (3) | 0.3754 (2) | 0.0266 (7) | |
N2 | 0.4378 (2) | −0.2820 (3) | 0.3824 (2) | 0.0296 (8) | |
N3 | 0.9794 (3) | 0.3747 (7) | 0.4301 (4) | 0.092 (2) | |
N4 | 0.0137 (3) | 0.6357 (6) | −0.1281 (3) | 0.078 (2) | |
C1 | 0.4700 (3) | 0.2827 (4) | 0.3357 (3) | 0.0305 (9) | |
C2 | 0.4736 (3) | 0.1613 (4) | 0.3339 (3) | 0.0307 (9) | |
C3 | 0.4328 (2) | 0.0952 (3) | 0.3768 (2) | 0.0262 (8) | |
C4 | 0.3910 (3) | 0.1582 (4) | 0.4181 (3) | 0.0303 (9) | |
C5 | 0.3900 (3) | 0.2796 (4) | 0.4160 (3) | 0.0299 (9) | |
C6 | 0.3787 (3) | −0.2203 (4) | 0.3949 (4) | 0.051 (2) | |
C7 | 0.3749 (3) | −0.0995 (4) | 0.3931 (4) | 0.049 (1) | |
C8 | 0.4352 (2) | −0.0352 (3) | 0.3782 (3) | 0.0274 (9) | |
C9 | 0.4962 (3) | −0.0985 (4) | 0.3646 (3) | 0.0315 (9) | |
C10 | 0.4948 (3) | −0.2201 (4) | 0.3671 (3) | 0.0304 (9) | |
C11 | 0.6038 (3) | 0.4843 (3) | 0.4491 (3) | 0.0262 (9) | |
C12 | 0.6860 (2) | 0.4605 (3) | 0.4438 (3) | 0.0275 (9) | |
C13 | 0.6959 (3) | 0.4482 (4) | 0.3682 (3) | 0.037 (1) | |
C14 | 0.7713 (3) | 0.4246 (5) | 0.3628 (3) | 0.045 (1) | |
C15 | 0.8373 (3) | 0.4161 (5) | 0.4361 (3) | 0.046 (1) | |
C16 | 0.8280 (3) | 0.4290 (5) | 0.5120 (3) | 0.049 (1) | |
C17 | 0.7527 (3) | 0.4495 (4) | 0.5164 (3) | 0.039 (1) | |
C18 | 0.9170 (3) | 0.3919 (6) | 0.4319 (4) | 0.063 (2) | |
C19 | 0.3216 (3) | 0.5499 (3) | 0.2394 (3) | 0.0295 (9) | |
C20 | 0.2553 (3) | 0.5700 (4) | 0.1578 (3) | 0.033 (1) | |
C21 | 0.1755 (3) | 0.5627 (5) | 0.1540 (3) | 0.043 (1) | |
C22 | 0.1138 (3) | 0.5805 (5) | 0.0795 (3) | 0.052 (1) | |
C23 | 0.1322 (3) | 0.6053 (5) | 0.0091 (3) | 0.045 (1) | |
C24 | 0.2115 (3) | 0.6130 (5) | 0.0123 (3) | 0.049 (1) | |
C25 | 0.2734 (3) | 0.5951 (5) | 0.0873 (3) | 0.043 (1) | |
C26 | 0.0662 (3) | 0.6229 (6) | −0.0688 (3) | 0.057 (2) | |
C27 | 0.1618 (8) | 1.0708 (13) | 0.3334 (7) | 0.146 (5) | |
C28 | 0.0255 (9) | 1.0816 (15) | 0.2338 (8) | 0.23 (1) | |
C29 | 0.082 (1) | 1.234 (1) | 0.3260 (7) | 0.215 (9) | |
C30 | 0.2831 (7) | 0.2219 (8) | 0.5971 (9) | 0.139 (5) | |
C31 | 0.1444 (5) | 0.259 (1) | 0.5708 (9) | 0.182 (7) | |
C32 | 0.2368 (9) | 0.2518 (9) | 0.7068 (5) | 0.161 (6) | |
H1w1 | 0.2150 | 0.6829 | 0.3149 | 0.382* | |
H1w2 | 0.1862 | 0.7951 | 0.3181 | 0.382* | |
H1 | 0.4983 | 0.3258 | 0.3070 | 0.037* | |
H2 | 0.5032 | 0.1230 | 0.3043 | 0.037* | |
H4 | 0.3629 | 0.1176 | 0.4481 | 0.036* | |
H5 | 0.3603 | 0.3202 | 0.4445 | 0.036* | |
H6 | 0.3368 | −0.2623 | 0.4058 | 0.062* | |
H7 | 0.3309 | −0.0603 | 0.4020 | 0.059* | |
H9 | 0.5390 | −0.0589 | 0.3536 | 0.038* | |
H10 | 0.5374 | −0.2618 | 0.3572 | 0.036* | |
H13 | 0.6505 | 0.4559 | 0.3189 | 0.044* | |
H14 | 0.7777 | 0.4145 | 0.3106 | 0.054* | |
H16 | 0.8736 | 0.4236 | 0.5613 | 0.059* | |
H17 | 0.7460 | 0.4562 | 0.5688 | 0.046* | |
H21 | 0.1633 | 0.5454 | 0.2025 | 0.052* | |
H22 | 0.0591 | 0.5759 | 0.0766 | 0.062* | |
H24 | 0.2236 | 0.6304 | −0.0362 | 0.059* | |
H25 | 0.3281 | 0.6001 | 0.0902 | 0.051* | |
H27 | 0.1976 | 1.1139 | 0.3784 | 0.175* | |
H28a | −0.0241 | 1.0923 | 0.2467 | 0.342* | |
H28b | 0.0326 | 0.9980 | 0.2242 | 0.342* | |
H28c | 0.0217 | 1.1267 | 0.1840 | 0.342* | |
H29a | 0.0359 | 1.2384 | 0.3451 | 0.323* | |
H29b | 0.0750 | 1.2911 | 0.2812 | 0.323* | |
H29c | 0.1317 | 1.2529 | 0.3721 | 0.323* | |
H30 | 0.3319 | 0.2079 | 0.6418 | 0.167* | |
H31a | 0.1159 | 0.3072 | 0.5990 | 0.273* | |
H31b | 0.1185 | 0.1812 | 0.5585 | 0.273* | |
H31c | 0.1425 | 0.2969 | 0.5191 | 0.273* | |
H32a | 0.2172 | 0.3275 | 0.7194 | 0.242* | |
H32b | 0.2948 | 0.2447 | 0.7378 | 0.242* | |
H32c | 0.2078 | 0.1877 | 0.7227 | 0.242* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0293 (3) | 0.0142 (3) | 0.0306 (3) | 0.0009 (2) | 0.0161 (2) | 0.0012 (2) |
O1 | 0.030 (2) | 0.022 (1) | 0.041 (2) | 0.003 (1) | 0.018 (1) | 0.007 (1) |
O2 | 0.046 (2) | 0.030 (2) | 0.038 (2) | −0.001 (1) | 0.028 (2) | −0.002 (1) |
O3 | 0.037 (2) | 0.041 (2) | 0.037 (2) | −0.002 (1) | 0.018 (1) | 0.001 (1) |
O4 | 0.036 (2) | 0.031 (2) | 0.039 (2) | 0.003 (1) | 0.018 (1) | 0.004 (1) |
O5 | 0.084 (4) | 0.138 (5) | 0.091 (4) | 0.050 (4) | 0.049 (3) | 0.035 (4) |
O6 | 0.151 (5) | 0.093 (4) | 0.128 (5) | −0.001 (4) | 0.119 (5) | −0.009 (3) |
O1w | 0.29 (2) | 0.34 (2) | 0.334 (19) | 0.024 (15) | 0.12 (2) | −0.05 (2) |
N5 | 0.100 (5) | 0.150 (7) | 0.076 (4) | 0.067 (5) | 0.054 (4) | 0.051 (5) |
N6 | 0.039 (2) | 0.053 (3) | 0.041 (2) | −0.003 (2) | 0.017 (2) | −0.003 (2) |
N1 | 0.037 (2) | 0.015 (2) | 0.033 (2) | 0.001 (1) | 0.019 (2) | 0.002 (1) |
N2 | 0.034 (2) | 0.016 (2) | 0.043 (2) | 0.001 (1) | 0.019 (2) | 0.001 (2) |
N3 | 0.041 (3) | 0.136 (6) | 0.112 (5) | 0.013 (3) | 0.040 (3) | −0.010 (4) |
N4 | 0.059 (3) | 0.119 (5) | 0.045 (3) | 0.011 (3) | 0.007 (3) | 0.009 (3) |
C1 | 0.044 (2) | 0.021 (2) | 0.035 (2) | −0.001 (2) | 0.025 (2) | 0.001 (2) |
C2 | 0.043 (2) | 0.020 (2) | 0.038 (2) | 0.000 (2) | 0.026 (2) | 0.000 (2) |
C3 | 0.032 (2) | 0.018 (2) | 0.031 (2) | 0.000 (2) | 0.014 (2) | −0.001 (2) |
C4 | 0.042 (2) | 0.021 (2) | 0.036 (2) | −0.005 (2) | 0.023 (2) | 0.001 (2) |
C5 | 0.040 (2) | 0.022 (2) | 0.037 (2) | 0.000 (2) | 0.025 (2) | −0.003 (2) |
C6 | 0.046 (3) | 0.018 (2) | 0.109 (5) | −0.001 (2) | 0.051 (3) | 0.003 (3) |
C7 | 0.046 (3) | 0.019 (2) | 0.100 (4) | 0.007 (2) | 0.047 (3) | 0.006 (2) |
C8 | 0.033 (2) | 0.018 (2) | 0.032 (2) | 0.001 (2) | 0.014 (2) | 0.000 (2) |
C9 | 0.038 (2) | 0.019 (2) | 0.045 (2) | −0.002 (2) | 0.024 (2) | 0.001 (2) |
C10 | 0.036 (2) | 0.021 (2) | 0.042 (2) | 0.001 (2) | 0.023 (2) | −0.001 (2) |
C11 | 0.035 (2) | 0.011 (2) | 0.036 (2) | −0.001 (2) | 0.019 (2) | −0.006 (2) |
C12 | 0.031 (2) | 0.019 (2) | 0.036 (2) | 0.001 (2) | 0.016 (2) | 0.001 (2) |
C13 | 0.032 (2) | 0.040 (3) | 0.040 (2) | 0.006 (2) | 0.016 (2) | 0.000 (2) |
C14 | 0.043 (3) | 0.053 (3) | 0.048 (3) | 0.006 (2) | 0.028 (2) | −0.003 (2) |
C15 | 0.035 (2) | 0.047 (3) | 0.063 (3) | 0.005 (2) | 0.026 (2) | 0.001 (3) |
C16 | 0.033 (2) | 0.061 (3) | 0.049 (3) | 0.003 (2) | 0.010 (2) | −0.002 (3) |
C17 | 0.041 (3) | 0.040 (3) | 0.036 (2) | 0.000 (2) | 0.015 (2) | −0.001 (2) |
C18 | 0.048 (3) | 0.074 (4) | 0.076 (4) | 0.009 (3) | 0.031 (3) | 0.002 (3) |
C19 | 0.036 (2) | 0.021 (2) | 0.036 (2) | −0.002 (2) | 0.018 (2) | 0.000 (2) |
C20 | 0.039 (2) | 0.029 (2) | 0.035 (2) | −0.002 (2) | 0.016 (2) | −0.002 (2) |
C21 | 0.042 (3) | 0.052 (3) | 0.041 (3) | −0.001 (2) | 0.020 (2) | 0.006 (2) |
C22 | 0.035 (3) | 0.071 (4) | 0.050 (3) | −0.002 (3) | 0.016 (2) | 0.003 (3) |
C23 | 0.045 (3) | 0.046 (3) | 0.039 (3) | 0.002 (2) | 0.009 (2) | 0.000 (2) |
C24 | 0.052 (3) | 0.063 (3) | 0.036 (3) | 0.004 (3) | 0.018 (2) | 0.006 (2) |
C25 | 0.040 (3) | 0.052 (3) | 0.038 (3) | −0.001 (2) | 0.016 (2) | 0.001 (2) |
C26 | 0.052 (3) | 0.071 (4) | 0.045 (3) | 0.004 (3) | 0.012 (3) | 0.002 (3) |
C27 | 0.16 (1) | 0.200 (13) | 0.115 (8) | 0.094 (10) | 0.098 (8) | 0.081 (9) |
C28 | 0.19 (1) | 0.29 (2) | 0.14 (1) | −0.11 (1) | −0.03 (1) | 0.12 (1) |
C29 | 0.35 (2) | 0.21 (2) | 0.081 (7) | 0.13 (2) | 0.07 (1) | 0.013 (9) |
C30 | 0.18 (1) | 0.072 (5) | 0.25 (1) | −0.023 (6) | 0.17 (1) | −0.022 (7) |
C31 | 0.061 (5) | 0.128 (9) | 0.29 (2) | −0.008 (6) | −0.028 (8) | 0.07 (1) |
C32 | 0.31 (2) | 0.082 (7) | 0.064 (5) | 0.022 (8) | 0.029 (8) | −0.005 (5) |
Geometric parameters (Å, º) top
Co1—O1 | 2.046 (3) | C16—C17 | 1.375 (7) |
Co1—O2i | 2.025 (3) | C19—C20 | 1.504 (6) |
Co1—O3 | 2.181 (3) | C20—C25 | 1.385 (6) |
Co1—O4 | 2.211 (3) | C20—C21 | 1.387 (7) |
Co1—N1 | 2.127 (3) | C21—C22 | 1.382 (7) |
Co1—N2ii | 2.135 (3) | C22—C23 | 1.385 (7) |
O1—C11 | 1.253 (5) | C23—C24 | 1.383 (7) |
O2—C11 | 1.245 (5) | C23—C26 | 1.455 (7) |
O2—Co1i | 2.025 (3) | C24—C25 | 1.390 (7) |
O3—C19 | 1.261 (5) | O1w—H1w1 | 0.88 |
O4—C19 | 1.259 (5) | O1w—H1w2 | 0.89 |
O5—C27 | 1.15 (1) | C1—H1 | 0.95 |
O6—C30 | 1.15 (1) | C2—H2 | 0.95 |
N5—C28 | 1.32 (1) | C4—H4 | 0.95 |
N5—C27 | 1.35 (1) | C5—H5 | 0.95 |
N5—C29 | 1.42 (2) | C6—H6 | 0.95 |
N6—C30 | 1.282 (9) | C7—H7 | 0.95 |
N6—C31 | 1.373 (9) | C9—H9 | 0.95 |
N6—C32 | 1.413 (9) | C10—H10 | 0.95 |
N1—C1 | 1.342 (5) | C13—H13 | 0.95 |
N1—C5 | 1.347 (5) | C14—H14 | 0.95 |
N2—C10 | 1.326 (5) | C16—H16 | 0.95 |
N2—C6 | 1.332 (6) | C17—H17 | 0.95 |
N2—Co1iii | 2.135 (3) | C21—H21 | 0.95 |
N3—C18 | 1.129 (7) | C22—H22 | 0.95 |
N4—C26 | 1.127 (7) | C24—H24 | 0.95 |
C1—C2 | 1.382 (6) | C25—H25 | 0.95 |
C2—C3 | 1.410 (6) | C27—H27 | 0.95 |
C3—C4 | 1.385 (6) | C28—H28a | 0.98 |
C3—C8 | 1.483 (5) | C28—H28b | 0.98 |
C4—C5 | 1.380 (6) | C28—H28c | 0.98 |
C6—C7 | 1.375 (6) | C29—H29a | 0.98 |
C7—C8 | 1.384 (6) | C29—H29b | 0.98 |
C8—C9 | 1.380 (6) | C29—H29c | 0.98 |
C9—C10 | 1.383 (6) | C30—H30 | 0.95 |
C11—C12 | 1.505 (6) | C31—H31a | 0.98 |
C12—C13 | 1.378 (6) | C31—H31b | 0.98 |
C12—C17 | 1.397 (6) | C31—H31c | 0.98 |
C13—C14 | 1.388 (6) | C32—H32a | 0.98 |
C14—C15 | 1.395 (7) | C32—H32b | 0.98 |
C15—C16 | 1.377 (7) | C32—H32c | 0.98 |
C15—C18 | 1.456 (7) | ||
O1—Co1—O2i | 119.1 (1) | C24—C23—C26 | 120.5 (5) |
O1—Co1—O3 | 150.2 (1) | C22—C23—C26 | 118.7 (5) |
O1—Co1—O4 | 90.2 (1) | C23—C24—C25 | 119.3 (5) |
O1—Co1—N1 | 88.5 (1) | C20—C25—C24 | 120.0 (5) |
O1—Co1—N2ii | 90.5 (1) | N4—C26—C23 | 178.2 (7) |
O2i—Co1—O3 | 90.7 (1) | O5—C27—N5 | 129 (2) |
O2i—Co1—O4 | 150.5 (1) | O6—C30—N6 | 134 (1) |
O2i—Co1—N1 | 92.3 (1) | H1w1—O1w—H1w2 | 102.7 |
O2i—Co1—N2ii | 87.5 (1) | N1—C1—H1 | 117.9 |
O3—Co1—O4 | 60.0 (1) | C2—C1—H1 | 117.9 |
O3—Co1—N1 | 92.2 (1) | C1—C2—H2 | 120.5 |
O3—Co1—N2ii | 89.0 (1) | C3—C2—H2 | 120.5 |
O4—Co1—N1 | 92.0 (1) | C5—C4—H4 | 119.7 |
O4—Co1—N2ii | 88.7 (1) | C3—C4—H4 | 119.7 |
N1—Co1—N2ii | 178.7 (1) | N1—C5—H5 | 118.4 |
C11—O1—Co1 | 121.0 (3) | C4—C5—H5 | 118.4 |
C11—O2—Co1i | 166.4 (3) | N2—C6—H6 | 118.1 |
C19—O3—Co1 | 89.9 (3) | C7—C6—H6 | 118.1 |
C19—O4—Co1 | 88.6 (2) | C6—C7—H7 | 120.1 |
C28—N5—C27 | 130 (1) | C8—C7—H7 | 120.1 |
C28—N5—C29 | 117 (1) | C8—C9—H9 | 120.2 |
C27—N5—C29 | 113 (1) | C10—C9—H9 | 120.2 |
C30—N6—C31 | 126 (1) | N2—C10—H10 | 118.0 |
C30—N6—C32 | 119 (1) | C9—C10—H10 | 118.0 |
C31—N6—C32 | 114.9 (9) | C12—C13—H13 | 119.5 |
C1—N1—C5 | 116.5 (3) | C14—C13—H13 | 119.5 |
C1—N1—Co1 | 120.7 (3) | C13—C14—H14 | 120.9 |
C5—N1—Co1 | 122.7 (3) | C15—C14—H14 | 120.9 |
C10—N2—C6 | 116.1 (4) | C17—C16—H16 | 120.0 |
C10—N2—Co1iii | 123.6 (3) | C15—C16—H16 | 120.0 |
C6—N2—Co1iii | 120.1 (3) | C16—C17—H17 | 120.0 |
N1—C1—C2 | 124.1 (4) | C12—C17—H17 | 120.0 |
C1—C2—C3 | 119.0 (4) | C22—C21—H21 | 120.1 |
C4—C3—C2 | 116.6 (4) | C20—C21—H21 | 120.1 |
C4—C3—C8 | 121.7 (4) | C21—C22—H22 | 120.2 |
C2—C3—C8 | 121.6 (4) | C23—C22—H22 | 120.2 |
C5—C4—C3 | 120.5 (4) | C23—C24—H24 | 120.3 |
N1—C5—C4 | 123.2 (4) | C25—C24—H24 | 120.3 |
N2—C6—C7 | 123.9 (4) | C20—C25—H25 | 120.0 |
C6—C7—C8 | 119.8 (4) | C24—C25—H25 | 120.0 |
C9—C8—C7 | 116.7 (4) | O5—C27—H27 | 115.7 |
C9—C8—C3 | 122.6 (4) | N5—C27—H27 | 115.7 |
C7—C8—C3 | 120.8 (4) | N5—C28—H28a | 109.5 |
C8—C9—C10 | 119.5 (4) | N5—C28—H28b | 109.5 |
N2—C10—C9 | 124.0 (4) | H28a—C28—H28b | 109.5 |
O2—C11—O1 | 125.0 (4) | N5—C28—H28c | 109.5 |
O2—C11—C12 | 117.6 (4) | H28a—C28—H28c | 109.5 |
O1—C11—C12 | 117.4 (4) | H28b—C28—H28c | 109.5 |
C13—C12—C17 | 119.6 (4) | N5—C29—H29a | 109.5 |
C13—C12—C11 | 120.8 (4) | N5—C29—H29b | 109.5 |
C17—C12—C11 | 119.6 (4) | H29a—C29—H29b | 109.5 |
C12—C13—C14 | 121.1 (4) | N5—C29—H29c | 109.5 |
C13—C14—C15 | 118.3 (5) | H29a—C29—H29c | 109.5 |
C16—C15—C14 | 121.0 (4) | H29b—C29—H29c | 109.5 |
C16—C15—C18 | 119.7 (5) | O6—C30—H30 | 112.8 |
C14—C15—C18 | 119.2 (5) | N6—C30—H30 | 112.8 |
C17—C16—C15 | 120.1 (5) | N6—C31—H31a | 109.5 |
C16—C17—C12 | 119.9 (4) | N6—C31—H31b | 109.5 |
N3—C18—C15 | 178.6 (8) | H31a—C31—H31b | 109.5 |
O4—C19—O3 | 121.3 (4) | N6—C31—H31c | 109.5 |
O4—C19—C20 | 119.6 (4) | H31a—C31—H31c | 109.5 |
O3—C19—C20 | 119.1 (4) | H31b—C31—H31c | 109.5 |
C25—C20—C21 | 120.3 (4) | N6—C32—H32a | 109.5 |
C25—C20—C19 | 120.6 (4) | N6—C32—H32b | 109.5 |
C21—C20—C19 | 119.2 (4) | H32a—C32—H32b | 109.5 |
C22—C21—C20 | 119.9 (5) | N6—C32—H32c | 109.5 |
C21—C22—C23 | 119.7 (5) | H32a—C32—H32c | 109.5 |
C24—C23—C22 | 120.9 (5) | H32b—C32—H32c | 109.5 |
O2i—Co1—O1—C11 | 22.7 (3) | C6—N2—C10—C9 | 0.8 (7) |
N1—Co1—O1—C11 | −69.1 (3) | Co1iii—N2—C10—C9 | 175.7 (3) |
N2ii—Co1—O1—C11 | 110.2 (3) | C8—C9—C10—N2 | −0.4 (7) |
O3—Co1—O1—C11 | −160.9 (3) | Co1i—O2—C11—O1 | −52.7 (15) |
O4—Co1—O1—C11 | −161.1 (3) | Co1i—O2—C11—C12 | 128.1 (12) |
O2i—Co1—O3—C19 | 174.4 (2) | Co1—O1—C11—O2 | −10.0 (5) |
O1—Co1—O3—C19 | −2.5 (4) | Co1—O1—C11—C12 | 169.1 (2) |
N1—Co1—O3—C19 | −93.3 (2) | O2—C11—C12—C13 | 161.1 (4) |
N2ii—Co1—O3—C19 | 86.8 (2) | O1—C11—C12—C13 | −18.1 (6) |
O4—Co1—O3—C19 | −2.3 (2) | O2—C11—C12—C17 | −18.1 (6) |
O2i—Co1—O4—C19 | −4.6 (4) | O1—C11—C12—C17 | 162.7 (4) |
O1—Co1—O4—C19 | −177.8 (2) | C17—C12—C13—C14 | 0.1 (7) |
N1—Co1—O4—C19 | 93.7 (2) | C11—C12—C13—C14 | −179.1 (4) |
N2ii—Co1—O4—C19 | −87.4 (2) | C12—C13—C14—C15 | −1.3 (8) |
O3—Co1—O4—C19 | 2.3 (2) | C13—C14—C15—C16 | 1.0 (8) |
O2i—Co1—N1—C1 | −155.3 (3) | C13—C14—C15—C18 | −179.8 (5) |
O1—Co1—N1—C1 | −36.3 (3) | C14—C15—C16—C17 | 0.5 (8) |
O3—Co1—N1—C1 | 113.9 (3) | C18—C15—C16—C17 | −178.7 (5) |
O4—Co1—N1—C1 | 53.9 (3) | C15—C16—C17—C12 | −1.7 (8) |
O2i—Co1—N1—C5 | 21.3 (3) | C13—C12—C17—C16 | 1.4 (7) |
O1—Co1—N1—C5 | 140.4 (3) | C11—C12—C17—C16 | −179.4 (4) |
O3—Co1—N1—C5 | −69.4 (3) | Co1—O4—C19—O3 | −4.0 (4) |
O4—Co1—N1—C5 | −129.5 (3) | Co1—O4—C19—C20 | 175.8 (3) |
C5—N1—C1—C2 | 0.5 (7) | Co1—O3—C19—O4 | 4.0 (4) |
Co1—N1—C1—C2 | 177.3 (3) | Co1—O3—C19—C20 | −175.7 (3) |
N1—C1—C2—C3 | −0.7 (7) | O4—C19—C20—C25 | −9.2 (6) |
C1—C2—C3—C4 | 0.2 (6) | O3—C19—C20—C25 | 170.6 (4) |
C1—C2—C3—C8 | −179.3 (4) | O4—C19—C20—C21 | 170.6 (4) |
C2—C3—C4—C5 | 0.4 (6) | O3—C19—C20—C21 | −9.6 (6) |
C8—C3—C4—C5 | 179.8 (4) | C25—C20—C21—C22 | 0.0 (8) |
C1—N1—C5—C4 | 0.2 (6) | C19—C20—C21—C22 | −179.8 (5) |
Co1—N1—C5—C4 | −176.6 (3) | C20—C21—C22—C23 | 0.2 (8) |
C3—C4—C5—N1 | −0.6 (7) | C21—C22—C23—C24 | −0.4 (9) |
C10—N2—C6—C7 | −0.3 (8) | C21—C22—C23—C26 | 179.6 (5) |
Co1iii—N2—C6—C7 | −175.4 (5) | C22—C23—C24—C25 | 0.3 (8) |
N2—C6—C7—C8 | −1 (1) | C26—C23—C24—C25 | −179.6 (5) |
C6—C7—C8—C9 | 1.0 (8) | C21—C20—C25—C24 | −0.1 (7) |
C6—C7—C8—C3 | −179.3 (5) | C19—C20—C25—C24 | 179.7 (5) |
C4—C3—C8—C9 | −156.3 (4) | C23—C24—C25—C20 | −0.1 (8) |
C2—C3—C8—C9 | 23.2 (6) | C28—N5—C27—O5 | 0.3 (18) |
C4—C3—C8—C7 | 24.0 (7) | C29—N5—C27—O5 | −172 (1) |
C2—C3—C8—C7 | −156.6 (5) | C31—N6—C30—O6 | 6 (2) |
C7—C8—C9—C10 | −0.5 (7) | C32—N6—C30—O6 | −178 (1) |
C3—C8—C9—C10 | 179.7 (4) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z; (iii) x, y−1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O3 | 0.88 | 2.29 | 3.14 (2) | 165 |
O1w—H1w2···O5 | 0.89 | 2.15 | 3.02 (2) | 165 |