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In a study to evaluate the impact of flexible positional isomeric ligands on the coordination geometry and self-assembly process of 3
d metal complexes, the synthesis of eight new cobalt(II) complexes with the 2-phenylimidazole (
LH) and 5-phenylimidazole (
L′H) ligands has been carried out. A variety of parameters/conditions have been probed using the general Co
II/
X−/
LH or
L′H (
X− = Cl
−, Br
−, I
−, NO
3−, NCS
−, ClO
4−, SO
42−) reaction system. Interestingly, X-ray analyses reveal two distinct groups of complexes: reactions with
LH only lead to tetrahedral or quasi-tetrahedral complexes {
i.e. [CoCl
2(
LH)
2] (
1), [CoI
2(
LH)
2] (
2), [Co(NO
3)
2(
LH)
2] (
3), [Co(NCS)
2(
LH)
2] (
4)}, whereas
L′H favours octahedral coordination {
i.e. [Co(
L′H)
4(MeCN)(H
2O)]I
2 (
5), [Co(
L′H)
4(MeCN)(H
2O)](NO
3)
2 (
6) and [Co(NCS)
2(
L′H)
4)]·2MeOH (
7·2MeOH)}. A tetrahedral [Co(NCS)
2(
L′H)
2)] (
8) complex was also concurrently isolated with complex
7. The effects of the positional isomeric ligands
LH and
L′H and of the coordinated inorganic anions on the stoichiometry and packing arrangements of the complexes are thoroughly discussed. The supramolecular assembly is firmly directed, in all types of complexes, by robust N—H
X (
X = Cl, I, O or S) motifs, leading to varying dimensionalities (1D, 2D or 3D) and packing arrangements. The formation of these motifs has been activated by choosing appropriate anions
X, acting as terminal ligands or counterions. At a second level of organization, additional subordinate C—H
X (
X = Cl, I, O or S), C—H
π and π
π intermolecular interactions complement the rigidity of the complexes' packing towards compact 3D assemblies. Hirshfeld surface analyses provided insight into the intermolecular interactions, allowed quantification of the individual contact types and comparison between the complexes.
Supporting information
CCDC references: 1914027; 1914028; 1914029; 1914030; 1914031; 1914032; 1914033; 1914034
For all structures, data collection: CrysAlis PRO 1.171.38.43 (Rigaku OD, 2015); cell refinement: CrysAlis PRO 1.171.38.43 (Rigaku OD, 2015); data reduction: CrysAlis PRO 1.171.38.43 (Rigaku OD, 2015); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014); molecular graphics: PLATON (Spek, 2011); Mercury (Bruno et al. 2002); DIAMOND (Brandenburg, 2014); X-SEED (Barbour, 2001); software used to prepare material for publication: WinGX (Farrugia, 2012).
Crystal data top
C18H16Cl2CoN4 | Dx = 1.551 Mg m−3 |
Mr = 418.18 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pca21 | Cell parameters from 6008 reflections |
a = 14.8764 (9) Å | θ = 3.0–29.0° |
b = 8.9742 (4) Å | µ = 1.26 mm−1 |
c = 26.8271 (9) Å | T = 100 K |
V = 3581.5 (3) Å3 | Prism, blue |
Z = 8 | 0.32 × 0.15 × 0.15 mm |
F(000) = 1704 | |
Data collection top
Oxford Diffraction SuperNova with Atlas CCD detector diffractometer | 6080 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 5795 reflections with I > 2σ(I) |
Detector resolution: 10.4223 pixels mm-1 | Rint = 0.030 |
ω scans | θmax = 27.0°, θmin = 3.0° |
Absorption correction: multi-scan CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | h = −12→19 |
Tmin = 0.667, Tmax = 1.000 | k = −9→11 |
11547 measured reflections | l = −31→34 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.027 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.068 | w = 1/[σ2(Fo2) + (0.0333P)2 + 0.5291P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
6080 reflections | Δρmax = 0.41 e Å−3 |
464 parameters | Δρmin = −0.28 e Å−3 |
5 restraints | Absolute structure: Refined as an inversion twin. |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.495 (15) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component inversion twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C2A | 0.4731 (3) | 0.4790 (4) | 0.68182 (15) | 0.0143 (8) | |
C2B | 0.3825 (2) | 0.2020 (4) | 0.55021 (14) | 0.0146 (7) | |
C2C | 0.6418 (3) | 0.2780 (4) | 0.46363 (14) | 0.0159 (8) | |
C2D | 0.7237 (3) | 0.0203 (4) | 0.33211 (15) | 0.0150 (8) | |
C4A | 0.3852 (3) | 0.6551 (4) | 0.65507 (14) | 0.0173 (8) | |
H4A | 0.3348 | 0.7052 | 0.6432 | 0.021* | |
C4B | 0.3486 (3) | 0.0478 (4) | 0.60959 (13) | 0.0174 (8) | |
H4B | 0.3314 | 0.0103 | 0.6405 | 0.021* | |
C4C | 0.6262 (3) | 0.4257 (4) | 0.40016 (14) | 0.0181 (8) | |
H4C | 0.6128 | 0.4607 | 0.3684 | 0.022* | |
C4D | 0.6410 (3) | −0.1637 (4) | 0.35724 (15) | 0.0190 (8) | |
H4D | 0.5921 | −0.2187 | 0.3687 | 0.023* | |
C5A | 0.4648 (3) | 0.7178 (4) | 0.66531 (15) | 0.0218 (8) | |
H5A | 0.4801 | 0.8177 | 0.6616 | 0.026* | |
C5B | 0.3706 (3) | −0.0347 (4) | 0.56942 (14) | 0.0183 (8) | |
H5B | 0.3714 | −0.1381 | 0.5674 | 0.022* | |
C5C | 0.6597 (3) | 0.5074 (4) | 0.43737 (14) | 0.0207 (8) | |
H5C | 0.6739 | 0.6083 | 0.4363 | 0.025* | |
C5D | 0.7228 (3) | −0.2188 (4) | 0.34705 (15) | 0.0215 (9) | |
H5D | 0.7410 | −0.3175 | 0.3501 | 0.026* | |
C6A | 0.5075 (3) | 0.3337 (4) | 0.69759 (13) | 0.0138 (7) | |
C6B | 0.3999 (3) | 0.3350 (4) | 0.52053 (14) | 0.0178 (8) | |
C6C | 0.6414 (3) | 0.1499 (4) | 0.49703 (14) | 0.0159 (8) | |
C6D | 0.7552 (3) | 0.1684 (4) | 0.31749 (13) | 0.0154 (7) | |
C7A | 0.4515 (3) | 0.2365 (4) | 0.72295 (15) | 0.0176 (8) | |
H7A | 0.3928 | 0.2642 | 0.7305 | 0.021* | |
C7B | 0.4404 (3) | 0.4582 (4) | 0.54174 (16) | 0.0230 (9) | |
H7B | 0.4569 | 0.4564 | 0.5752 | 0.028* | |
C7C | 0.6708 (3) | 0.0114 (4) | 0.48021 (16) | 0.0222 (9) | |
H7C | 0.6929 | 0.0009 | 0.4480 | 0.027* | |
C7D | 0.6998 (3) | 0.2604 (4) | 0.28959 (14) | 0.0175 (8) | |
H7D | 0.6428 | 0.2281 | 0.2802 | 0.021* | |
C8A | 0.4831 (3) | 0.0989 (4) | 0.73688 (13) | 0.0188 (8) | |
H8A | 0.4456 | 0.0327 | 0.7536 | 0.023* | |
C8B | 0.4562 (3) | 0.5834 (4) | 0.51360 (17) | 0.0291 (10) | |
H8B | 0.4831 | 0.6663 | 0.5281 | 0.035* | |
C8C | 0.6672 (3) | −0.1097 (4) | 0.51159 (16) | 0.0255 (9) | |
H8C | 0.6865 | −0.2023 | 0.5004 | 0.031* | |
C8D | 0.7296 (3) | 0.4011 (4) | 0.27574 (14) | 0.0191 (8) | |
H8D | 0.6924 | 0.4635 | 0.2573 | 0.023* | |
C9A | 0.5704 (3) | 0.0588 (4) | 0.72612 (14) | 0.0210 (8) | |
H9A | 0.5914 | −0.0349 | 0.7352 | 0.025* | |
C9B | 0.4321 (3) | 0.5869 (5) | 0.46344 (16) | 0.0318 (11) | |
H9B | 0.4419 | 0.6722 | 0.4445 | 0.038* | |
C9C | 0.6349 (3) | −0.0945 (4) | 0.55966 (15) | 0.0231 (9) | |
H9C | 0.6318 | −0.1771 | 0.5806 | 0.028* | |
C9D | 0.8142 (3) | 0.4483 (4) | 0.28920 (13) | 0.0195 (8) | |
H9D | 0.8341 | 0.5422 | 0.2796 | 0.023* | |
C10A | 0.6266 (3) | 0.1567 (4) | 0.70200 (14) | 0.0201 (8) | |
H10A | 0.6858 | 0.1296 | 0.6954 | 0.024* | |
C10B | 0.3936 (3) | 0.4627 (5) | 0.44212 (16) | 0.0282 (10) | |
H10B | 0.3784 | 0.4633 | 0.4085 | 0.034* | |
C10C | 0.6074 (3) | 0.0426 (4) | 0.57647 (15) | 0.0230 (8) | |
H10C | 0.5860 | 0.0528 | 0.6089 | 0.028* | |
C10D | 0.8694 (3) | 0.3576 (4) | 0.31670 (14) | 0.0203 (9) | |
H10D | 0.9262 | 0.3905 | 0.3260 | 0.024* | |
C11A | 0.5956 (3) | 0.2948 (4) | 0.68754 (14) | 0.0184 (8) | |
H11A | 0.6335 | 0.3612 | 0.6712 | 0.022* | |
C11B | 0.3775 (3) | 0.3374 (4) | 0.47050 (15) | 0.0208 (8) | |
H11B | 0.3514 | 0.2540 | 0.4559 | 0.025* | |
C11C | 0.6111 (3) | 0.1647 (4) | 0.54578 (14) | 0.0179 (8) | |
H11C | 0.5934 | 0.2575 | 0.5576 | 0.021* | |
C11D | 0.8405 (3) | 0.2165 (4) | 0.33060 (14) | 0.0192 (8) | |
H11D | 0.8783 | 0.1543 | 0.3487 | 0.023* | |
N1A | 0.5190 (2) | 0.6066 (3) | 0.68212 (12) | 0.0181 (7) | |
H1A | 0.5733 (13) | 0.613 (5) | 0.6920 (17) | 0.027* | |
N1B | 0.3914 (2) | 0.0634 (3) | 0.53248 (12) | 0.0174 (7) | |
H1B | 0.409 (3) | 0.043 (5) | 0.5028 (8) | 0.026* | |
N1C | 0.6691 (2) | 0.4142 (3) | 0.47731 (12) | 0.0202 (7) | |
H1C | 0.692 (3) | 0.433 (5) | 0.5058 (9) | 0.030* | |
N1D | 0.7739 (2) | −0.1022 (3) | 0.33140 (12) | 0.0186 (7) | |
H1D | 0.8288 (13) | −0.113 (5) | 0.3229 (18) | 0.028* | |
N3A | 0.3898 (2) | 0.5047 (3) | 0.66493 (13) | 0.0147 (7) | |
N3B | 0.3556 (2) | 0.1972 (3) | 0.59755 (11) | 0.0146 (6) | |
N3C | 0.6147 (2) | 0.2811 (3) | 0.41633 (12) | 0.0151 (6) | |
N3D | 0.6411 (2) | −0.0118 (3) | 0.34801 (13) | 0.0144 (7) | |
Cl1 | 0.20519 (7) | 0.48821 (10) | 0.58987 (4) | 0.0201 (2) | |
Cl2 | 0.21558 (6) | 0.24886 (9) | 0.69847 (3) | 0.01686 (19) | |
Cl3 | 0.46731 (6) | 0.24859 (10) | 0.31794 (3) | 0.01758 (19) | |
Cl4 | 0.45880 (7) | −0.01587 (10) | 0.42304 (4) | 0.0191 (2) | |
Co1 | 0.29988 (3) | 0.35776 (5) | 0.63889 (2) | 0.01224 (11) | |
Co2 | 0.54962 (3) | 0.12868 (5) | 0.37588 (2) | 0.01262 (11) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2A | 0.0143 (19) | 0.0161 (17) | 0.0126 (18) | −0.0029 (16) | 0.0003 (18) | −0.0015 (13) |
C2B | 0.0127 (18) | 0.0132 (16) | 0.0178 (16) | 0.0021 (15) | 0.0032 (15) | 0.0001 (13) |
C2C | 0.0113 (18) | 0.0183 (18) | 0.0181 (17) | −0.0027 (15) | 0.0024 (15) | −0.0047 (14) |
C2D | 0.019 (2) | 0.0153 (17) | 0.0110 (18) | 0.0030 (16) | −0.0016 (18) | −0.0017 (13) |
C4A | 0.020 (2) | 0.0126 (16) | 0.0192 (17) | 0.0007 (15) | −0.0004 (16) | 0.0022 (13) |
C4B | 0.020 (2) | 0.0147 (16) | 0.0173 (17) | 0.0036 (16) | 0.0018 (16) | 0.0038 (13) |
C4C | 0.020 (2) | 0.0180 (17) | 0.0164 (16) | −0.0022 (16) | 0.0020 (16) | 0.0024 (14) |
C4D | 0.022 (2) | 0.0120 (16) | 0.0231 (18) | −0.0024 (16) | 0.0029 (17) | −0.0030 (14) |
C5A | 0.029 (2) | 0.0112 (16) | 0.025 (2) | −0.0029 (17) | 0.0005 (18) | 0.0017 (15) |
C5B | 0.024 (2) | 0.0126 (16) | 0.0187 (17) | 0.0030 (16) | 0.0003 (16) | 0.0029 (13) |
C5C | 0.027 (2) | 0.0168 (18) | 0.0180 (18) | −0.0057 (17) | 0.0024 (18) | −0.0001 (14) |
C5D | 0.026 (2) | 0.0132 (17) | 0.025 (2) | 0.0025 (17) | 0.0042 (19) | −0.0008 (14) |
C6A | 0.0142 (19) | 0.0151 (16) | 0.0121 (16) | −0.0016 (16) | −0.0028 (15) | −0.0030 (13) |
C6B | 0.016 (2) | 0.0177 (17) | 0.0198 (18) | 0.0041 (16) | 0.0066 (17) | 0.0016 (14) |
C6C | 0.0125 (19) | 0.0191 (17) | 0.0161 (17) | −0.0004 (15) | −0.0030 (15) | −0.0015 (13) |
C6D | 0.0152 (19) | 0.0183 (17) | 0.0128 (17) | 0.0003 (16) | 0.0021 (15) | −0.0006 (14) |
C7A | 0.0143 (19) | 0.0206 (18) | 0.0178 (18) | 0.0010 (16) | −0.0001 (15) | 0.0000 (14) |
C7B | 0.026 (2) | 0.0190 (18) | 0.024 (2) | −0.0003 (18) | 0.0101 (18) | −0.0023 (16) |
C7C | 0.026 (2) | 0.0216 (19) | 0.0187 (19) | 0.0037 (17) | −0.0051 (18) | −0.0067 (15) |
C7D | 0.0141 (19) | 0.0223 (19) | 0.0161 (18) | −0.0019 (16) | 0.0006 (15) | −0.0005 (14) |
C8A | 0.022 (2) | 0.0186 (17) | 0.0158 (18) | −0.0036 (17) | −0.0014 (17) | 0.0030 (14) |
C8B | 0.032 (3) | 0.0183 (19) | 0.037 (2) | −0.0032 (18) | 0.013 (2) | −0.0042 (17) |
C8C | 0.031 (2) | 0.0163 (17) | 0.030 (2) | 0.0072 (18) | −0.010 (2) | −0.0052 (16) |
C8D | 0.020 (2) | 0.0176 (17) | 0.0197 (18) | 0.0057 (17) | 0.0000 (17) | 0.0047 (15) |
C9A | 0.026 (2) | 0.0180 (18) | 0.0193 (18) | 0.0050 (18) | −0.0046 (18) | −0.0018 (14) |
C9B | 0.038 (3) | 0.022 (2) | 0.035 (2) | 0.003 (2) | 0.017 (2) | 0.0139 (17) |
C9C | 0.026 (2) | 0.0185 (18) | 0.025 (2) | −0.0029 (18) | −0.0084 (18) | 0.0061 (15) |
C9D | 0.028 (2) | 0.0143 (17) | 0.0165 (18) | −0.0034 (18) | 0.0028 (17) | −0.0014 (14) |
C10A | 0.015 (2) | 0.0263 (19) | 0.0188 (18) | 0.0061 (16) | −0.0007 (16) | −0.0022 (15) |
C10B | 0.029 (2) | 0.031 (2) | 0.024 (2) | 0.007 (2) | 0.0067 (19) | 0.0114 (17) |
C10C | 0.023 (2) | 0.0251 (19) | 0.0206 (19) | −0.0042 (18) | −0.0024 (18) | 0.0007 (15) |
C10D | 0.018 (2) | 0.025 (2) | 0.0173 (18) | −0.0071 (16) | −0.0015 (17) | −0.0053 (14) |
C11A | 0.0157 (19) | 0.0234 (19) | 0.0161 (17) | −0.0025 (17) | 0.0012 (16) | 0.0007 (14) |
C11B | 0.020 (2) | 0.0209 (18) | 0.0213 (19) | 0.0024 (17) | 0.0019 (17) | 0.0038 (15) |
C11C | 0.020 (2) | 0.0160 (17) | 0.0179 (18) | 0.0002 (16) | −0.0031 (16) | −0.0019 (13) |
C11D | 0.017 (2) | 0.0221 (19) | 0.0186 (18) | 0.0029 (17) | −0.0016 (16) | −0.0003 (14) |
N1A | 0.0162 (17) | 0.0173 (15) | 0.0209 (16) | −0.0036 (15) | −0.0041 (15) | 0.0004 (13) |
N1B | 0.0211 (17) | 0.0153 (14) | 0.0158 (14) | 0.0022 (14) | 0.0030 (14) | −0.0019 (12) |
N1C | 0.028 (2) | 0.0178 (15) | 0.0148 (15) | −0.0074 (15) | −0.0028 (15) | −0.0026 (12) |
N1D | 0.0160 (17) | 0.0169 (15) | 0.0230 (17) | 0.0068 (14) | 0.0042 (15) | 0.0036 (13) |
N3A | 0.0179 (18) | 0.0108 (14) | 0.0154 (17) | −0.0021 (12) | 0.0005 (15) | 0.0008 (11) |
N3B | 0.0161 (16) | 0.0118 (14) | 0.0161 (15) | 0.0029 (13) | 0.0010 (13) | 0.0020 (11) |
N3C | 0.0131 (16) | 0.0140 (14) | 0.0184 (14) | −0.0019 (13) | 0.0005 (13) | −0.0028 (11) |
N3D | 0.0149 (18) | 0.0139 (15) | 0.0145 (17) | −0.0005 (13) | 0.0011 (15) | 0.0004 (11) |
Cl1 | 0.0230 (5) | 0.0216 (4) | 0.0157 (5) | 0.0087 (4) | −0.0023 (4) | 0.0014 (3) |
Cl2 | 0.0137 (4) | 0.0177 (4) | 0.0192 (4) | −0.0005 (4) | 0.0019 (4) | 0.0033 (3) |
Cl3 | 0.0139 (4) | 0.0182 (4) | 0.0207 (4) | 0.0013 (4) | −0.0021 (4) | 0.0031 (3) |
Cl4 | 0.0231 (5) | 0.0178 (4) | 0.0164 (5) | −0.0053 (4) | 0.0039 (4) | −0.0017 (3) |
Co1 | 0.0128 (2) | 0.0113 (2) | 0.0126 (2) | 0.00102 (18) | 0.0001 (2) | 0.00035 (18) |
Co2 | 0.0127 (2) | 0.0116 (2) | 0.0136 (2) | 0.00019 (18) | 0.0001 (2) | −0.00131 (18) |
Geometric parameters (Å, º) top
C2A—N1A | 1.333 (5) | C7C—C8C | 1.376 (6) |
C2A—N3A | 1.340 (5) | C7C—H7C | 0.9300 |
C2A—C6A | 1.463 (5) | C7D—C8D | 1.389 (5) |
C2B—N3B | 1.332 (5) | C7D—H7D | 0.9300 |
C2B—N1B | 1.338 (5) | C8A—C9A | 1.378 (6) |
C2B—C6B | 1.458 (5) | C8A—H8A | 0.9300 |
C2C—N3C | 1.331 (5) | C8B—C9B | 1.393 (6) |
C2C—N1C | 1.340 (5) | C8B—H8B | 0.9300 |
C2C—C6C | 1.457 (5) | C8C—C9C | 1.383 (6) |
C2D—N1D | 1.329 (5) | C8C—H8C | 0.9300 |
C2D—N3D | 1.333 (5) | C8D—C9D | 1.376 (6) |
C2D—C6D | 1.463 (5) | C8D—H8D | 0.9300 |
C4A—C5A | 1.340 (6) | C9A—C10A | 1.374 (6) |
C4A—N3A | 1.377 (4) | C9A—H9A | 0.9300 |
C4A—H4A | 0.9300 | C9B—C10B | 1.378 (6) |
C4B—C5B | 1.348 (5) | C9B—H9B | 0.9300 |
C4B—N3B | 1.382 (4) | C9C—C10C | 1.373 (6) |
C4B—H4B | 0.9300 | C9C—H9C | 0.9300 |
C4C—C5C | 1.336 (5) | C9D—C10D | 1.371 (6) |
C4C—N3C | 1.379 (4) | C9D—H9D | 0.9300 |
C4C—H4C | 0.9300 | C10A—C11A | 1.378 (5) |
C4D—C5D | 1.341 (6) | C10A—H10A | 0.9300 |
C4D—N3D | 1.386 (4) | C10B—C11B | 1.378 (5) |
C4D—H4D | 0.9300 | C10B—H10B | 0.9300 |
C5A—N1A | 1.359 (5) | C10C—C11C | 1.371 (5) |
C5A—H5A | 0.9300 | C10C—H10C | 0.9300 |
C5B—N1B | 1.361 (5) | C10D—C11D | 1.388 (5) |
C5B—H5B | 0.9300 | C10D—H10D | 0.9300 |
C5C—N1C | 1.367 (5) | C11A—H11A | 0.9300 |
C5C—H5C | 0.9300 | C11B—H11B | 0.9300 |
C5D—N1D | 1.360 (5) | C11C—H11C | 0.9300 |
C5D—H5D | 0.9300 | C11D—H11D | 0.9300 |
C6A—C11A | 1.383 (5) | N1A—H1A | 0.852 (13) |
C6A—C7A | 1.385 (5) | N1B—H1B | 0.858 (13) |
C6B—C7B | 1.382 (6) | N1C—H1C | 0.855 (13) |
C6B—C11B | 1.383 (6) | N1D—H1D | 0.852 (13) |
C6C—C11C | 1.389 (5) | N3A—Co1 | 2.004 (3) |
C6C—C7C | 1.393 (5) | N3B—Co1 | 1.999 (3) |
C6D—C7D | 1.386 (5) | N3C—Co2 | 1.997 (3) |
C6D—C11D | 1.385 (6) | N3D—Co2 | 2.000 (3) |
C7A—C8A | 1.373 (5) | Cl1—Co1 | 2.2548 (11) |
C7A—H7A | 0.9300 | Cl2—Co1 | 2.2544 (10) |
C7B—C8B | 1.374 (6) | Cl3—Co2 | 2.2524 (10) |
C7B—H7B | 0.9300 | Cl4—Co2 | 2.2603 (11) |
| | | |
N1A—C2A—N3A | 109.1 (3) | C10A—C9A—C8A | 120.3 (4) |
N1A—C2A—C6A | 125.8 (4) | C10A—C9A—H9A | 119.8 |
N3A—C2A—C6A | 125.0 (3) | C8A—C9A—H9A | 119.8 |
N3B—C2B—N1B | 109.8 (3) | C10B—C9B—C8B | 119.4 (4) |
N3B—C2B—C6B | 126.9 (3) | C10B—C9B—H9B | 120.3 |
N1B—C2B—C6B | 123.3 (3) | C8B—C9B—H9B | 120.3 |
N3C—C2C—N1C | 109.5 (3) | C10C—C9C—C8C | 119.8 (4) |
N3C—C2C—C6C | 127.0 (3) | C10C—C9C—H9C | 120.1 |
N1C—C2C—C6C | 123.5 (3) | C8C—C9C—H9C | 120.1 |
N1D—C2D—N3D | 110.1 (3) | C10D—C9D—C8D | 120.4 (3) |
N1D—C2D—C6D | 124.7 (4) | C10D—C9D—H9D | 119.8 |
N3D—C2D—C6D | 125.3 (3) | C8D—C9D—H9D | 119.8 |
C5A—C4A—N3A | 109.2 (3) | C9A—C10A—C11A | 120.3 (4) |
C5A—C4A—H4A | 125.4 | C9A—C10A—H10A | 119.9 |
N3A—C4A—H4A | 125.4 | C11A—C10A—H10A | 119.9 |
C5B—C4B—N3B | 109.1 (3) | C9B—C10B—C11B | 120.2 (4) |
C5B—C4B—H4B | 125.4 | C9B—C10B—H10B | 119.9 |
N3B—C4B—H4B | 125.4 | C11B—C10B—H10B | 119.9 |
C5C—C4C—N3C | 109.2 (3) | C11C—C10C—C9C | 120.4 (4) |
C5C—C4C—H4C | 125.4 | C11C—C10C—H10C | 119.8 |
N3C—C4C—H4C | 125.4 | C9C—C10C—H10C | 119.8 |
C5D—C4D—N3D | 109.0 (4) | C9D—C10D—C11D | 120.0 (4) |
C5D—C4D—H4D | 125.5 | C9D—C10D—H10D | 120.0 |
N3D—C4D—H4D | 125.5 | C11D—C10D—H10D | 120.0 |
C4A—C5A—N1A | 106.5 (3) | C10A—C11A—C6A | 119.3 (4) |
C4A—C5A—H5A | 126.8 | C10A—C11A—H11A | 120.4 |
N1A—C5A—H5A | 126.8 | C6A—C11A—H11A | 120.4 |
C4B—C5B—N1B | 106.4 (3) | C10B—C11B—C6B | 120.5 (4) |
C4B—C5B—H5B | 126.8 | C10B—C11B—H11B | 119.8 |
N1B—C5B—H5B | 126.8 | C6B—C11B—H11B | 119.8 |
C4C—C5C—N1C | 106.7 (3) | C10C—C11C—C6C | 120.1 (4) |
C4C—C5C—H5C | 126.6 | C10C—C11C—H11C | 119.9 |
N1C—C5C—H5C | 126.6 | C6C—C11C—H11C | 119.9 |
C4D—C5D—N1D | 106.7 (3) | C6D—C11D—C10D | 120.0 (4) |
C4D—C5D—H5D | 126.7 | C6D—C11D—H11D | 120.0 |
N1D—C5D—H5D | 126.7 | C10D—C11D—H11D | 120.0 |
C11A—C6A—C7A | 120.4 (3) | C2A—N1A—C5A | 109.0 (3) |
C11A—C6A—C2A | 120.0 (3) | C2A—N1A—H1A | 123 (3) |
C7A—C6A—C2A | 119.6 (3) | C5A—N1A—H1A | 128 (3) |
C7B—C6B—C11B | 119.5 (4) | C2B—N1B—C5B | 108.7 (3) |
C7B—C6B—C2B | 120.5 (4) | C2B—N1B—H1B | 124 (3) |
C11B—C6B—C2B | 120.0 (3) | C5B—N1B—H1B | 128 (3) |
C11C—C6C—C7C | 119.5 (3) | C2C—N1C—C5C | 108.2 (3) |
C11C—C6C—C2C | 120.3 (3) | C2C—N1C—H1C | 123 (3) |
C7C—C6C—C2C | 120.2 (4) | C5C—N1C—H1C | 128 (3) |
C7D—C6D—C11D | 119.7 (3) | C2D—N1D—C5D | 108.6 (3) |
C7D—C6D—C2D | 119.7 (3) | C2D—N1D—H1D | 129 (3) |
C11D—C6D—C2D | 120.5 (4) | C5D—N1D—H1D | 122 (3) |
C8A—C7A—C6A | 119.6 (4) | C2A—N3A—C4A | 106.2 (3) |
C8A—C7A—H7A | 120.2 | C2A—N3A—Co1 | 128.5 (2) |
C6A—C7A—H7A | 120.2 | C4A—N3A—Co1 | 123.0 (3) |
C8B—C7B—C6B | 120.2 (4) | C2B—N3B—C4B | 106.1 (3) |
C8B—C7B—H7B | 119.9 | C2B—N3B—Co1 | 129.1 (2) |
C6B—C7B—H7B | 119.9 | C4B—N3B—Co1 | 122.5 (2) |
C8C—C7C—C6C | 119.6 (4) | C2C—N3C—C4C | 106.4 (3) |
C8C—C7C—H7C | 120.2 | C2C—N3C—Co2 | 130.5 (3) |
C6C—C7C—H7C | 120.2 | C4C—N3C—Co2 | 122.3 (2) |
C6D—C7D—C8D | 119.7 (3) | C2D—N3D—C4D | 105.7 (3) |
C6D—C7D—H7D | 120.1 | C2D—N3D—Co2 | 127.7 (2) |
C8D—C7D—H7D | 120.1 | C4D—N3D—Co2 | 123.6 (3) |
C7A—C8A—C9A | 120.1 (4) | N3B—Co1—N3A | 113.02 (13) |
C7A—C8A—H8A | 120.0 | N3B—Co1—Cl2 | 108.16 (9) |
C9A—C8A—H8A | 120.0 | N3A—Co1—Cl2 | 114.16 (10) |
C7B—C8B—C9B | 120.3 (4) | N3B—Co1—Cl1 | 108.05 (9) |
C7B—C8B—H8B | 119.8 | N3A—Co1—Cl1 | 106.18 (9) |
C9B—C8B—H8B | 119.8 | Cl2—Co1—Cl1 | 106.93 (4) |
C7C—C8C—C9C | 120.5 (4) | N3C—Co2—N3D | 107.77 (13) |
C7C—C8C—H8C | 119.8 | N3C—Co2—Cl3 | 108.14 (9) |
C9C—C8C—H8C | 119.8 | N3D—Co2—Cl3 | 114.40 (10) |
C9D—C8D—C7D | 120.1 (3) | N3C—Co2—Cl4 | 112.26 (9) |
C9D—C8D—H8D | 119.9 | N3D—Co2—Cl4 | 104.73 (9) |
C7D—C8D—H8D | 119.9 | Cl3—Co2—Cl4 | 109.60 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···Cl2i | 0.85 (2) | 2.46 (3) | 3.229 (3) | 151 (4) |
N1B—H1B···Cl4 | 0.86 (3) | 2.33 (3) | 3.183 (3) | 179 (6) |
N1C—H1C···Cl1i | 0.85 (3) | 2.37 (3) | 3.190 (3) | 161 (4) |
N1D—H1D···Cl3ii | 0.85 (2) | 2.40 (3) | 3.184 (3) | 154 (4) |
Symmetry codes: (i) x+1/2, −y+1, z; (ii) x+1/2, −y, z. |
Crystal data top
C18H16CoI2N4 | F(000) = 1140 |
Mr = 601.08 | Dx = 2.020 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5817 (4) Å | Cell parameters from 2244 reflections |
b = 18.625 (1) Å | θ = 2.9–28.6° |
c = 14.2346 (11) Å | µ = 4.00 mm−1 |
β = 100.448 (7)° | T = 100 K |
V = 1976.7 (2) Å3 | Plate, blue |
Z = 4 | 0.21 × 0.14 × 0.07 mm |
Data collection top
Agilent Technologies SuperNova with Atlas detector diffractometer | 2136 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 1949 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.022 |
Detector resolution: 10.4223 pixels mm-1 | θmax = 27.0°, θmin = 2.9° |
ω scans | h = −9→9 |
Absorption correction: multi-scan CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | k = −21→23 |
Tmin = 0.605, Tmax = 1.000 | l = −18→8 |
4313 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)] = 0.022 | Hydrogen site location: mixed |
wR(F2) = 0.057 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0312P)2 + 0.5775P] where P = (Fo2 + 2Fc2)/3 |
2136 reflections | (Δ/σ)max < 0.001 |
117 parameters | Δρmax = 0.57 e Å−3 |
1 restraint | Δρmin = −0.62 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I | 0.64585 (2) | 0.10658 (2) | 0.13296 (2) | 0.01864 (8) | |
Co | 0.5000 | 0.18344 (2) | 0.2500 | 0.01323 (12) | |
N1 | 0.1429 (3) | 0.31000 (12) | 0.06410 (16) | 0.0180 (5) | |
H1 | 0.114 (4) | 0.3442 (12) | 0.0256 (18) | 0.027* | |
N3 | 0.3093 (3) | 0.23837 (11) | 0.16429 (15) | 0.0137 (4) | |
C7 | 0.6293 (3) | 0.33201 (15) | 0.14263 (18) | 0.0168 (5) | |
H7 | 0.6579 | 0.2834 | 0.1480 | 0.020* | |
C6 | 0.4513 (3) | 0.35340 (14) | 0.12489 (19) | 0.0167 (5) | |
C2 | 0.3065 (3) | 0.30033 (13) | 0.11763 (18) | 0.0149 (5) | |
C4 | 0.1401 (3) | 0.20807 (16) | 0.13807 (19) | 0.0180 (6) | |
H4 | 0.1036 | 0.1645 | 0.1600 | 0.022* | |
C11 | 0.4104 (4) | 0.42593 (15) | 0.1160 (2) | 0.0259 (6) | |
H11 | 0.2913 | 0.4407 | 0.1039 | 0.031* | |
C9 | 0.7235 (4) | 0.45505 (15) | 0.1442 (2) | 0.0299 (7) | |
H9 | 0.8145 | 0.4892 | 0.1514 | 0.036* | |
C5 | 0.0375 (3) | 0.25212 (15) | 0.0757 (2) | 0.0206 (6) | |
H5 | −0.0810 | 0.2447 | 0.0464 | 0.025* | |
C8 | 0.7648 (4) | 0.38288 (15) | 0.1525 (2) | 0.0222 (6) | |
H8 | 0.8841 | 0.3683 | 0.1647 | 0.027* | |
C10 | 0.5460 (4) | 0.47631 (16) | 0.1250 (3) | 0.0356 (8) | |
H10 | 0.5176 | 0.5248 | 0.1182 | 0.043* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I | 0.01936 (11) | 0.01558 (12) | 0.02040 (12) | 0.00516 (6) | 0.00205 (8) | −0.00084 (6) |
Co | 0.0117 (2) | 0.0111 (2) | 0.0157 (2) | 0.000 | −0.00068 (18) | 0.000 |
N1 | 0.0149 (10) | 0.0222 (11) | 0.0161 (11) | 0.0067 (9) | 0.0007 (9) | 0.0012 (9) |
N3 | 0.0100 (9) | 0.0138 (10) | 0.0168 (11) | 0.0008 (8) | 0.0005 (8) | −0.0018 (9) |
C7 | 0.0208 (12) | 0.0146 (13) | 0.0150 (13) | 0.0005 (10) | 0.0028 (10) | 0.0005 (10) |
C6 | 0.0203 (12) | 0.0165 (12) | 0.0139 (13) | 0.0001 (10) | 0.0047 (10) | −0.0010 (10) |
C2 | 0.0150 (11) | 0.0160 (12) | 0.0131 (12) | 0.0041 (9) | 0.0008 (10) | −0.0026 (10) |
C4 | 0.0120 (12) | 0.0196 (14) | 0.0217 (14) | −0.0003 (9) | 0.0012 (11) | −0.0046 (11) |
C11 | 0.0236 (13) | 0.0193 (14) | 0.0359 (17) | 0.0063 (11) | 0.0086 (13) | 0.0033 (13) |
C9 | 0.0302 (16) | 0.0206 (14) | 0.043 (2) | −0.0093 (12) | 0.0178 (14) | −0.0078 (14) |
C5 | 0.0119 (11) | 0.0287 (14) | 0.0202 (14) | 0.0030 (10) | 0.0001 (10) | −0.0068 (12) |
C8 | 0.0182 (13) | 0.0273 (14) | 0.0221 (15) | −0.0025 (11) | 0.0064 (11) | −0.0042 (12) |
C10 | 0.0389 (18) | 0.0142 (14) | 0.058 (2) | −0.0007 (12) | 0.0218 (17) | 0.0013 (14) |
Geometric parameters (Å, º) top
I—Co | 2.5915 (3) | C6—C11 | 1.386 (4) |
Co—N3 | 1.997 (2) | C6—C2 | 1.467 (3) |
Co—N3i | 1.997 (2) | C4—C5 | 1.348 (4) |
Co—Ii | 2.5916 (3) | C4—H4 | 0.9300 |
N1—C2 | 1.345 (3) | C11—C10 | 1.380 (4) |
N1—C5 | 1.369 (4) | C11—H11 | 0.9300 |
N1—H1 | 0.843 (10) | C9—C8 | 1.381 (4) |
N3—C2 | 1.330 (3) | C9—C10 | 1.382 (5) |
N3—C4 | 1.389 (3) | C9—H9 | 0.9300 |
C7—C6 | 1.386 (3) | C5—H5 | 0.9300 |
C7—C8 | 1.386 (4) | C8—H8 | 0.9300 |
C7—H7 | 0.9300 | C10—H10 | 0.9300 |
| | | |
N3—Co—N3i | 118.35 (11) | N1—C2—C6 | 123.5 (2) |
N3—Co—I | 103.67 (6) | C5—C4—N3 | 108.9 (2) |
N3i—Co—I | 109.25 (6) | C5—C4—H4 | 125.5 |
N3—Co—Ii | 109.25 (6) | N3—C4—H4 | 125.5 |
N3i—Co—Ii | 103.67 (6) | C10—C11—C6 | 120.2 (2) |
I—Co—Ii | 112.933 (18) | C10—C11—H11 | 119.9 |
C2—N1—C5 | 109.0 (2) | C6—C11—H11 | 119.9 |
C2—N1—H1 | 125 (2) | C8—C9—C10 | 119.6 (3) |
C5—N1—H1 | 126 (2) | C8—C9—H9 | 120.2 |
C2—N3—C4 | 106.8 (2) | C10—C9—H9 | 120.2 |
C2—N3—Co | 133.94 (16) | C4—C5—N1 | 106.2 (2) |
C4—N3—Co | 119.15 (17) | C4—C5—H5 | 126.9 |
C6—C7—C8 | 120.1 (3) | N1—C5—H5 | 126.9 |
C6—C7—H7 | 120.0 | C9—C8—C7 | 120.3 (3) |
C8—C7—H7 | 120.0 | C9—C8—H8 | 119.9 |
C7—C6—C11 | 119.4 (2) | C7—C8—H8 | 119.9 |
C7—C6—C2 | 120.7 (2) | C11—C10—C9 | 120.4 (3) |
C11—C6—C2 | 119.9 (2) | C11—C10—H10 | 119.8 |
N3—C2—N1 | 109.2 (2) | C9—C10—H10 | 119.8 |
N3—C2—C6 | 127.3 (2) | | |
Symmetry code: (i) −x+1, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Iii | 0.84 (2) | 2.86 (3) | 3.584 (2) | 144 (2) |
Symmetry code: (ii) −x+1/2, −y+1/2, −z. |
Crystal data top
C18H16CoN6O6 | F(000) = 964 |
Mr = 471.30 | Dx = 1.596 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 9.4982 (9) Å | Cell parameters from 2592 reflections |
b = 14.9627 (11) Å | θ = 3.2–72.3° |
c = 14.5081 (14) Å | µ = 7.32 mm−1 |
β = 107.938 (10)° | T = 100 K |
V = 1961.6 (3) Å3 | Prism, purple |
Z = 4 | 0.18 × 0.13 × 0.09 mm |
Data collection top
Agilent Technologies SuperNova with Atlas detector diffractometer | 3563 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 2849 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.041 |
Detector resolution: 10.4223 pixels mm-1 | θmax = 68.5°, θmin = 4.4° |
ω scans | h = −11→10 |
Absorption correction: multi-scan CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | k = −18→17 |
Tmin = 0.671, Tmax = 1.000 | l = −12→17 |
7276 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)] = 0.048 | Hydrogen site location: mixed |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0392P)2 + 1.633P] where P = (Fo2 + 2Fc2)/3 |
3563 reflections | (Δ/σ)max = 0.001 |
286 parameters | Δρmax = 0.27 e Å−3 |
2 restraints | Δρmin = −0.45 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Co | 0.94789 (5) | 0.27868 (3) | 0.58536 (3) | 0.02162 (14) | |
N1A | 1.3875 (3) | 0.33670 (19) | 0.60016 (19) | 0.0252 (6) | |
H1A | 1.4778 (16) | 0.326 (2) | 0.606 (3) | 0.038* | |
C2A | 1.2830 (3) | 0.2755 (2) | 0.6001 (2) | 0.0228 (6) | |
N3A | 1.1525 (3) | 0.31661 (17) | 0.58262 (18) | 0.0223 (5) | |
C4A | 1.1774 (3) | 0.4063 (2) | 0.5701 (2) | 0.0258 (7) | |
H4A | 1.1056 | 0.4508 | 0.5562 | 0.031* | |
C5A | 1.3229 (3) | 0.4190 (2) | 0.5812 (2) | 0.0270 (7) | |
H5A | 1.3693 | 0.4729 | 0.5768 | 0.032* | |
C6A | 1.3145 (3) | 0.1803 (2) | 0.6187 (2) | 0.0255 (7) | |
C7A | 1.2024 (4) | 0.1165 (2) | 0.5868 (2) | 0.0303 (7) | |
H7A | 1.1078 | 0.1343 | 0.5503 | 0.036* | |
C8A | 1.2313 (4) | 0.0269 (2) | 0.6094 (3) | 0.0392 (9) | |
H8A | 1.1560 | −0.0152 | 0.5885 | 0.047* | |
C9A | 1.3724 (4) | 0.0000 (3) | 0.6631 (3) | 0.0428 (9) | |
H9A | 1.3914 | −0.0597 | 0.6802 | 0.051* | |
C10A | 1.4845 (4) | 0.0624 (3) | 0.6910 (3) | 0.0398 (9) | |
H10A | 1.5801 | 0.0437 | 0.7243 | 0.048* | |
C11A | 1.4571 (3) | 0.1521 (2) | 0.6703 (2) | 0.0325 (8) | |
H11A | 1.5334 | 0.1935 | 0.6908 | 0.039* | |
N1B | 1.0491 (3) | 0.08421 (19) | 0.7992 (2) | 0.0283 (6) | |
H1B | 1.102 (4) | 0.055 (2) | 0.8468 (18) | 0.042* | |
C2B | 1.0705 (3) | 0.1665 (2) | 0.7693 (2) | 0.0236 (7) | |
N3B | 0.9615 (3) | 0.18704 (17) | 0.68944 (18) | 0.0230 (6) | |
C4B | 0.8672 (3) | 0.1141 (2) | 0.6705 (3) | 0.0298 (7) | |
H4B | 0.7803 | 0.1098 | 0.6190 | 0.036* | |
C5B | 0.9204 (3) | 0.0501 (2) | 0.7383 (3) | 0.0328 (8) | |
H5B | 0.8784 | −0.0053 | 0.7425 | 0.039* | |
C6B | 1.1979 (3) | 0.2220 (2) | 0.8192 (2) | 0.0255 (7) | |
C7B | 1.1813 (4) | 0.3129 (2) | 0.8327 (2) | 0.0335 (8) | |
H7B | 1.0884 | 0.3394 | 0.8102 | 0.040* | |
C8B | 1.3046 (4) | 0.3640 (3) | 0.8800 (3) | 0.0439 (10) | |
H8B | 1.2943 | 0.4249 | 0.8891 | 0.053* | |
C9B | 1.4426 (4) | 0.3245 (3) | 0.9136 (2) | 0.0479 (11) | |
H9B | 1.5249 | 0.3588 | 0.9454 | 0.058* | |
C10B | 1.4587 (4) | 0.2343 (3) | 0.9002 (3) | 0.0435 (10) | |
H10B | 1.5519 | 0.2081 | 0.9223 | 0.052* | |
C11B | 1.3374 (3) | 0.1829 (3) | 0.8542 (2) | 0.0332 (8) | |
H11B | 1.3484 | 0.1219 | 0.8464 | 0.040* | |
N1 | 0.8206 (3) | 0.2518 (2) | 0.3997 (2) | 0.0318 (7) | |
O1 | 0.8483 (2) | 0.19681 (15) | 0.47246 (15) | 0.0282 (5) | |
O2 | 0.8512 (2) | 0.33213 (17) | 0.42164 (18) | 0.0376 (6) | |
O3 | 0.7668 (3) | 0.22440 (19) | 0.31765 (17) | 0.0450 (7) | |
N2 | 0.7467 (3) | 0.38976 (18) | 0.61369 (18) | 0.0249 (6) | |
O4 | 0.8840 (2) | 0.40133 (15) | 0.61863 (16) | 0.0281 (5) | |
O5 | 0.6984 (2) | 0.31153 (14) | 0.59877 (15) | 0.0251 (5) | |
O6 | 0.6716 (2) | 0.45384 (16) | 0.62207 (18) | 0.0362 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co | 0.0153 (2) | 0.0250 (3) | 0.0237 (3) | −0.0015 (2) | 0.00489 (19) | 0.0002 (2) |
N1A | 0.0148 (11) | 0.0335 (15) | 0.0290 (15) | 0.0004 (11) | 0.0091 (11) | −0.0030 (11) |
C2A | 0.0167 (13) | 0.0300 (17) | 0.0224 (16) | −0.0009 (12) | 0.0072 (12) | −0.0018 (13) |
N3A | 0.0165 (11) | 0.0283 (14) | 0.0223 (14) | −0.0009 (10) | 0.0059 (10) | −0.0008 (10) |
C4A | 0.0188 (14) | 0.0298 (17) | 0.0295 (18) | 0.0004 (13) | 0.0084 (13) | −0.0006 (13) |
C5A | 0.0226 (15) | 0.0291 (18) | 0.0304 (18) | −0.0030 (13) | 0.0097 (13) | −0.0014 (13) |
C6A | 0.0242 (15) | 0.0307 (17) | 0.0248 (17) | 0.0031 (13) | 0.0123 (13) | 0.0004 (13) |
C7A | 0.0287 (16) | 0.0328 (18) | 0.0332 (19) | 0.0007 (14) | 0.0150 (14) | −0.0055 (14) |
C8A | 0.042 (2) | 0.034 (2) | 0.050 (2) | 0.0010 (16) | 0.0269 (18) | −0.0046 (17) |
C9A | 0.052 (2) | 0.034 (2) | 0.054 (2) | 0.0158 (18) | 0.035 (2) | 0.0080 (18) |
C10A | 0.0361 (19) | 0.050 (2) | 0.037 (2) | 0.0189 (18) | 0.0176 (16) | 0.0095 (17) |
C11A | 0.0250 (16) | 0.042 (2) | 0.0332 (19) | 0.0065 (15) | 0.0123 (14) | 0.0023 (15) |
N1B | 0.0236 (14) | 0.0298 (15) | 0.0299 (16) | 0.0021 (11) | 0.0059 (12) | 0.0095 (12) |
C2B | 0.0192 (14) | 0.0277 (17) | 0.0257 (17) | 0.0023 (12) | 0.0097 (13) | 0.0017 (13) |
N3B | 0.0166 (11) | 0.0252 (14) | 0.0266 (14) | 0.0011 (10) | 0.0056 (11) | 0.0015 (11) |
C4B | 0.0207 (15) | 0.0279 (18) | 0.038 (2) | −0.0036 (13) | 0.0040 (13) | 0.0006 (14) |
C5B | 0.0256 (16) | 0.0264 (18) | 0.043 (2) | −0.0018 (14) | 0.0062 (15) | 0.0043 (15) |
C6B | 0.0215 (14) | 0.0381 (19) | 0.0178 (16) | −0.0044 (13) | 0.0070 (12) | 0.0038 (14) |
C7B | 0.0283 (16) | 0.041 (2) | 0.0283 (19) | −0.0076 (15) | 0.0049 (14) | 0.0046 (15) |
C8B | 0.052 (2) | 0.047 (2) | 0.028 (2) | −0.0228 (19) | 0.0062 (17) | 0.0012 (16) |
C9B | 0.036 (2) | 0.082 (3) | 0.0169 (19) | −0.029 (2) | −0.0048 (15) | 0.0108 (18) |
C10B | 0.0231 (17) | 0.077 (3) | 0.026 (2) | −0.0086 (18) | 0.0022 (14) | 0.0209 (19) |
C11B | 0.0221 (15) | 0.054 (2) | 0.0243 (18) | 0.0003 (15) | 0.0080 (14) | 0.0123 (15) |
N1 | 0.0197 (12) | 0.0466 (19) | 0.0295 (17) | −0.0027 (12) | 0.0082 (12) | 0.0008 (13) |
O1 | 0.0253 (11) | 0.0360 (13) | 0.0213 (12) | −0.0012 (10) | 0.0043 (9) | −0.0026 (9) |
O2 | 0.0315 (12) | 0.0377 (15) | 0.0427 (15) | −0.0051 (11) | 0.0102 (11) | 0.0076 (11) |
O3 | 0.0389 (14) | 0.073 (2) | 0.0201 (14) | −0.0050 (13) | 0.0050 (11) | −0.0065 (13) |
N2 | 0.0167 (12) | 0.0312 (15) | 0.0257 (15) | −0.0032 (11) | 0.0046 (11) | −0.0016 (11) |
O4 | 0.0135 (9) | 0.0312 (12) | 0.0397 (13) | −0.0034 (9) | 0.0082 (9) | −0.0039 (10) |
O5 | 0.0188 (10) | 0.0270 (12) | 0.0274 (12) | −0.0042 (9) | 0.0041 (9) | −0.0021 (9) |
O6 | 0.0216 (11) | 0.0308 (13) | 0.0575 (17) | 0.0043 (10) | 0.0143 (11) | −0.0088 (12) |
Geometric parameters (Å, º) top
Co—N3B | 2.014 (3) | N1B—C5B | 1.368 (4) |
Co—O1 | 2.031 (2) | N1B—H1B | 0.838 (10) |
Co—N3A | 2.037 (2) | C2B—N3B | 1.330 (4) |
Co—O4 | 2.037 (2) | C2B—C6B | 1.463 (4) |
Co—O2 | 2.404 (2) | N3B—C4B | 1.385 (4) |
N1A—C2A | 1.351 (4) | C4B—C5B | 1.353 (5) |
N1A—C5A | 1.366 (4) | C4B—H4B | 0.9300 |
N1A—H1A | 0.852 (10) | C5B—H5B | 0.9300 |
C2A—N3A | 1.336 (4) | C6B—C7B | 1.390 (5) |
C2A—C6A | 1.463 (4) | C6B—C11B | 1.393 (4) |
N3A—C4A | 1.384 (4) | C7B—C8B | 1.390 (5) |
C4A—C5A | 1.354 (4) | C7B—H7B | 0.9300 |
C4A—H4A | 0.9300 | C8B—C9B | 1.383 (6) |
C5A—H5A | 0.9300 | C8B—H8B | 0.9300 |
C6A—C11A | 1.396 (4) | C9B—C10B | 1.378 (6) |
C6A—C7A | 1.398 (4) | C9B—H9B | 0.9300 |
C7A—C8A | 1.388 (5) | C10B—C11B | 1.375 (5) |
C7A—H7A | 0.9300 | C10B—H10B | 0.9300 |
C8A—C9A | 1.386 (5) | C11B—H11B | 0.9300 |
C8A—H8A | 0.9300 | N1—O3 | 1.213 (4) |
C9A—C10A | 1.379 (5) | N1—O2 | 1.254 (4) |
C9A—H9A | 0.9300 | N1—O1 | 1.300 (4) |
C10A—C11A | 1.383 (5) | N2—O6 | 1.223 (3) |
C10A—H10A | 0.9300 | N2—O5 | 1.252 (3) |
C11A—H11A | 0.9300 | N2—O4 | 1.295 (3) |
N1B—C2B | 1.341 (4) | | |
| | | |
N3B—Co—O1 | 95.77 (10) | C2B—N1B—C5B | 109.1 (3) |
N3B—Co—N3A | 111.28 (10) | C2B—N1B—H1B | 129 (3) |
O1—Co—N3A | 111.25 (9) | C5B—N1B—H1B | 122 (3) |
N3B—Co—O4 | 113.00 (10) | N3B—C2B—N1B | 109.8 (3) |
O1—Co—O4 | 129.47 (9) | N3B—C2B—C6B | 127.0 (3) |
N3A—Co—O4 | 96.29 (9) | N1B—C2B—C6B | 123.1 (3) |
N3B—Co—O2 | 152.12 (9) | C2B—N3B—C4B | 105.8 (3) |
O1—Co—O2 | 57.49 (9) | C2B—N3B—Co | 131.6 (2) |
N3A—Co—O2 | 87.96 (9) | C4B—N3B—Co | 120.0 (2) |
O4—Co—O2 | 83.30 (9) | C5B—C4B—N3B | 109.8 (3) |
C2A—N1A—C5A | 109.1 (2) | C5B—C4B—H4B | 125.1 |
C2A—N1A—H1A | 126 (3) | N3B—C4B—H4B | 125.1 |
C5A—N1A—H1A | 125 (3) | C4B—C5B—N1B | 105.4 (3) |
N3A—C2A—N1A | 109.0 (3) | C4B—C5B—H5B | 127.3 |
N3A—C2A—C6A | 127.5 (3) | N1B—C5B—H5B | 127.3 |
N1A—C2A—C6A | 123.5 (3) | C7B—C6B—C11B | 119.8 (3) |
C2A—N3A—C4A | 106.6 (2) | C7B—C6B—C2B | 120.9 (3) |
C2A—N3A—Co | 134.7 (2) | C11B—C6B—C2B | 119.4 (3) |
C4A—N3A—Co | 118.38 (19) | C6B—C7B—C8B | 119.5 (3) |
C5A—C4A—N3A | 109.3 (3) | C6B—C7B—H7B | 120.2 |
C5A—C4A—H4A | 125.3 | C8B—C7B—H7B | 120.2 |
N3A—C4A—H4A | 125.3 | C9B—C8B—C7B | 120.1 (4) |
C4A—C5A—N1A | 106.0 (3) | C9B—C8B—H8B | 119.9 |
C4A—C5A—H5A | 127.0 | C7B—C8B—H8B | 119.9 |
N1A—C5A—H5A | 127.0 | C10B—C9B—C8B | 120.2 (3) |
C11A—C6A—C7A | 119.1 (3) | C10B—C9B—H9B | 119.9 |
C11A—C6A—C2A | 120.2 (3) | C8B—C9B—H9B | 119.9 |
C7A—C6A—C2A | 120.7 (3) | C11B—C10B—C9B | 120.2 (3) |
C8A—C7A—C6A | 120.4 (3) | C11B—C10B—H10B | 119.9 |
C8A—C7A—H7A | 119.8 | C9B—C10B—H10B | 119.9 |
C6A—C7A—H7A | 119.8 | C10B—C11B—C6B | 120.2 (4) |
C9A—C8A—C7A | 120.0 (4) | C10B—C11B—H11B | 119.9 |
C9A—C8A—H8A | 120.0 | C6B—C11B—H11B | 119.9 |
C7A—C8A—H8A | 120.0 | O3—N1—O2 | 124.6 (3) |
C10A—C9A—C8A | 119.6 (4) | O3—N1—O1 | 120.1 (3) |
C10A—C9A—H9A | 120.2 | O2—N1—O1 | 115.3 (3) |
C8A—C9A—H9A | 120.2 | N1—O1—Co | 101.58 (18) |
C9A—C10A—C11A | 121.1 (3) | N1—O2—Co | 85.42 (18) |
C9A—C10A—H10A | 119.4 | O6—N2—O5 | 123.8 (2) |
C11A—C10A—H10A | 119.4 | O6—N2—O4 | 119.8 (3) |
C10A—C11A—C6A | 119.7 (3) | O5—N2—O4 | 116.3 (2) |
C10A—C11A—H11A | 120.1 | N2—O4—Co | 103.59 (18) |
C6A—C11A—H11A | 120.1 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O5i | 0.85 (2) | 2.14 (2) | 2.983 (4) | 171 (4) |
N1B—H1B···O4ii | 0.84 (3) | 2.35 (3) | 2.974 (4) | 132 (3) |
N1B—H1B···O6ii | 0.84 (3) | 2.55 (4) | 3.206 (4) | 135 (3) |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, y−1/2, −z+3/2. |
Crystal data top
C20H16CoN6S2 | F(000) = 1896 |
Mr = 463.44 | Dx = 1.482 Mg m−3 |
Monoclinic, I2/a | Mo Kα radiation, λ = 0.71073 Å |
a = 17.5108 (14) Å | Cell parameters from 2206 reflections |
b = 13.8088 (13) Å | θ = 4.6–28.3° |
c = 18.9150 (16) Å | µ = 1.05 mm−1 |
β = 114.745 (9)° | T = 100 K |
V = 4153.7 (7) Å3 | Prism, blue |
Z = 8 | 0.15 × 0.10 × 0.09 mm |
Data collection top
Oxford Diffraction SuperNova with Atlas CCD detector diffractometer | 4413 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 3003 reflections with I > 2σ(I) |
Detector resolution: 10.4223 pixels mm-1 | Rint = 0.065 |
ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | h = −22→17 |
Tmin = 0.665, Tmax = 1.000 | k = −15→17 |
9606 measured reflections | l = −24→23 |
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)] = 0.054 | Hydrogen site location: mixed |
wR(F2) = 0.151 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0617P)2] where P = (Fo2 + 2Fc2)/3 |
4413 reflections | (Δ/σ)max = 0.001 |
268 parameters | Δρmax = 0.90 e Å−3 |
1 restraint | Δρmin = −0.84 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Co | 0.62170 (2) | 0.56587 (4) | 0.24871 (2) | 0.02358 (17) | |
C2A | 0.51801 (18) | 0.4464 (2) | 0.31250 (18) | 0.0227 (7) | |
C2B | 0.71798 (19) | 0.4339 (2) | 0.18356 (19) | 0.0224 (7) | |
C4A | 0.6213 (2) | 0.5236 (3) | 0.40307 (18) | 0.0292 (8) | |
H4A | 0.6694 | 0.5611 | 0.4280 | 0.035* | |
C4B | 0.61548 (19) | 0.5123 (3) | 0.09384 (18) | 0.0275 (8) | |
H4B | 0.5686 | 0.5517 | 0.0696 | 0.033* | |
C5A | 0.5751 (2) | 0.4832 (3) | 0.4376 (2) | 0.0320 (9) | |
H5A | 0.5851 | 0.4874 | 0.4898 | 0.038* | |
C5B | 0.6564 (2) | 0.4655 (3) | 0.0573 (2) | 0.0320 (9) | |
H5B | 0.6434 | 0.4666 | 0.0043 | 0.038* | |
C6A | 0.46063 (18) | 0.4052 (2) | 0.23887 (19) | 0.0239 (8) | |
C6B | 0.77741 (19) | 0.3920 (2) | 0.25700 (18) | 0.0215 (7) | |
C7A | 0.4883 (2) | 0.3823 (3) | 0.18236 (19) | 0.0281 (8) | |
H7A | 0.5448 | 0.3901 | 0.1929 | 0.034* | |
C7B | 0.7523 (2) | 0.3711 (3) | 0.31584 (18) | 0.0254 (8) | |
H7B | 0.6969 | 0.3819 | 0.3081 | 0.030* | |
C8A | 0.4331 (2) | 0.3479 (3) | 0.1105 (2) | 0.0392 (10) | |
H8A | 0.4525 | 0.3329 | 0.0729 | 0.047* | |
C8B | 0.8094 (2) | 0.3342 (3) | 0.38565 (19) | 0.0286 (8) | |
H8B | 0.7922 | 0.3199 | 0.4248 | 0.034* | |
C9A | 0.3495 (2) | 0.3357 (3) | 0.0945 (2) | 0.0475 (12) | |
H9A | 0.3122 | 0.3132 | 0.0460 | 0.057* | |
C9B | 0.8926 (2) | 0.3182 (3) | 0.3982 (2) | 0.0304 (9) | |
H9B | 0.9310 | 0.2940 | 0.4457 | 0.036* | |
C10A | 0.3208 (2) | 0.3570 (3) | 0.1506 (3) | 0.0458 (11) | |
H10A | 0.2645 | 0.3474 | 0.1398 | 0.055* | |
C10B | 0.9176 (2) | 0.3383 (3) | 0.3397 (2) | 0.0296 (8) | |
H10B | 0.9727 | 0.3264 | 0.3473 | 0.036* | |
C11A | 0.37491 (19) | 0.3923 (3) | 0.2226 (2) | 0.0320 (9) | |
H11A | 0.3551 | 0.4075 | 0.2598 | 0.038* | |
C11B | 0.86089 (19) | 0.3761 (2) | 0.26988 (19) | 0.0238 (8) | |
H11B | 0.8785 | 0.3911 | 0.2311 | 0.029* | |
N1A | 0.51046 (17) | 0.4350 (2) | 0.38003 (17) | 0.0283 (7) | |
H1A | 0.4761 (19) | 0.397 (2) | 0.387 (2) | 0.042* | |
N1B | 0.72080 (17) | 0.4162 (2) | 0.11392 (16) | 0.0275 (7) | |
H1B | 0.757 (2) | 0.378 (3) | 0.110 (2) | 0.041* | |
N3A | 0.58572 (15) | 0.5002 (2) | 0.32495 (15) | 0.0252 (6) | |
N3B | 0.65360 (15) | 0.4930 (2) | 0.17253 (15) | 0.0231 (6) | |
N1 | 0.52229 (17) | 0.6411 (2) | 0.18263 (16) | 0.0279 (7) | |
C1 | 0.4587 (2) | 0.6756 (3) | 0.14190 (19) | 0.0241 (8) | |
S1 | 0.36848 (5) | 0.72505 (7) | 0.08600 (5) | 0.0304 (3) | |
N2 | 0.72600 (17) | 0.6298 (2) | 0.31726 (17) | 0.0327 (7) | |
C2 | 0.7899 (2) | 0.6578 (3) | 0.36301 (19) | 0.0270 (8) | |
S2 | 0.87915 (5) | 0.69905 (8) | 0.42763 (6) | 0.0376 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co | 0.0172 (2) | 0.0267 (3) | 0.0263 (3) | −0.00093 (17) | 0.00859 (18) | −0.0028 (2) |
C2A | 0.0191 (15) | 0.025 (2) | 0.0233 (18) | 0.0036 (13) | 0.0077 (12) | 0.0017 (15) |
C2B | 0.0211 (16) | 0.023 (2) | 0.0246 (18) | −0.0027 (13) | 0.0108 (13) | −0.0010 (15) |
C4A | 0.0274 (17) | 0.036 (2) | 0.0211 (19) | 0.0004 (16) | 0.0073 (13) | −0.0044 (17) |
C4B | 0.0214 (16) | 0.033 (2) | 0.0253 (19) | 0.0028 (15) | 0.0072 (13) | 0.0028 (16) |
C5A | 0.0346 (19) | 0.036 (2) | 0.024 (2) | 0.0059 (17) | 0.0110 (14) | 0.0002 (17) |
C5B | 0.0350 (19) | 0.038 (2) | 0.0205 (19) | 0.0004 (17) | 0.0086 (14) | −0.0025 (17) |
C6A | 0.0167 (15) | 0.021 (2) | 0.0293 (19) | 0.0016 (13) | 0.0050 (13) | 0.0051 (15) |
C6B | 0.0221 (15) | 0.0202 (19) | 0.0221 (18) | −0.0007 (13) | 0.0092 (13) | −0.0026 (15) |
C7A | 0.0241 (17) | 0.025 (2) | 0.028 (2) | −0.0026 (14) | 0.0040 (13) | −0.0031 (16) |
C7B | 0.0199 (15) | 0.029 (2) | 0.0250 (19) | −0.0001 (14) | 0.0076 (13) | 0.0012 (16) |
C8A | 0.039 (2) | 0.033 (2) | 0.032 (2) | 0.0036 (17) | 0.0014 (16) | −0.0065 (18) |
C8B | 0.0295 (18) | 0.032 (2) | 0.0235 (19) | −0.0010 (15) | 0.0101 (14) | 0.0029 (16) |
C9A | 0.029 (2) | 0.040 (3) | 0.046 (3) | 0.0070 (17) | −0.0118 (17) | −0.013 (2) |
C9B | 0.0238 (17) | 0.033 (2) | 0.028 (2) | −0.0011 (15) | 0.0036 (14) | 0.0042 (17) |
C10A | 0.0164 (17) | 0.029 (2) | 0.074 (3) | −0.0035 (16) | 0.0008 (17) | −0.002 (2) |
C10B | 0.0207 (16) | 0.027 (2) | 0.038 (2) | 0.0002 (14) | 0.0098 (14) | −0.0005 (17) |
C11A | 0.0204 (17) | 0.021 (2) | 0.054 (2) | −0.0016 (14) | 0.0150 (15) | 0.0014 (18) |
C11B | 0.0263 (17) | 0.018 (2) | 0.0295 (19) | −0.0005 (13) | 0.0144 (14) | −0.0016 (15) |
N1A | 0.0258 (15) | 0.030 (2) | 0.0301 (17) | 0.0037 (12) | 0.0130 (12) | 0.0059 (14) |
N1B | 0.0264 (15) | 0.031 (2) | 0.0270 (17) | 0.0017 (13) | 0.0129 (12) | −0.0026 (14) |
N3A | 0.0187 (13) | 0.0319 (18) | 0.0231 (15) | 0.0006 (12) | 0.0067 (10) | −0.0005 (13) |
N3B | 0.0198 (13) | 0.0273 (18) | 0.0213 (15) | 0.0000 (12) | 0.0078 (10) | −0.0008 (13) |
N1 | 0.0270 (15) | 0.0261 (18) | 0.0360 (18) | 0.0025 (13) | 0.0185 (13) | 0.0038 (14) |
C1 | 0.0290 (18) | 0.021 (2) | 0.0274 (19) | −0.0037 (14) | 0.0171 (14) | −0.0025 (15) |
S1 | 0.0239 (4) | 0.0340 (6) | 0.0324 (5) | 0.0037 (4) | 0.0109 (3) | 0.0099 (4) |
N2 | 0.0221 (14) | 0.037 (2) | 0.0411 (19) | −0.0026 (13) | 0.0156 (13) | −0.0092 (15) |
C2 | 0.0250 (17) | 0.026 (2) | 0.034 (2) | 0.0021 (15) | 0.0168 (15) | −0.0055 (16) |
S2 | 0.0217 (4) | 0.0442 (7) | 0.0399 (6) | −0.0005 (4) | 0.0058 (4) | −0.0176 (5) |
Geometric parameters (Å, º) top
Co—N2 | 1.953 (3) | C7A—C8A | 1.381 (4) |
Co—N1 | 1.962 (3) | C7A—H7A | 0.9300 |
Co—N3A | 2.015 (3) | C7B—C8B | 1.377 (4) |
Co—N3B | 2.019 (3) | C7B—H7B | 0.9300 |
C2A—N3A | 1.334 (4) | C8A—C9A | 1.376 (5) |
C2A—N1A | 1.347 (4) | C8A—H8A | 0.9300 |
C2A—C6A | 1.450 (4) | C8B—C9B | 1.393 (4) |
C2B—N3B | 1.335 (4) | C8B—H8B | 0.9300 |
C2B—N1B | 1.361 (4) | C9A—C10A | 1.382 (6) |
C2B—C6B | 1.462 (4) | C9A—H9A | 0.9300 |
C4A—C5A | 1.355 (5) | C9B—C10B | 1.378 (4) |
C4A—N3A | 1.381 (4) | C9B—H9B | 0.9300 |
C4A—H4A | 0.9300 | C10A—C11A | 1.381 (5) |
C4B—C5B | 1.350 (4) | C10A—H10A | 0.9300 |
C4B—N3B | 1.379 (4) | C10B—C11B | 1.380 (4) |
C4B—H4B | 0.9300 | C10B—H10B | 0.9300 |
C5A—N1A | 1.370 (4) | C11A—H11A | 0.9300 |
C5A—H5A | 0.9300 | C11B—H11B | 0.9300 |
C5B—N1B | 1.368 (4) | N1A—H1A | 0.851 (10) |
C5B—H5B | 0.9300 | N1B—H1B | 0.84 (4) |
C6A—C7A | 1.382 (5) | N1—C1 | 1.158 (4) |
C6A—C11A | 1.412 (4) | C1—S1 | 1.638 (3) |
C6B—C7B | 1.388 (4) | N2—C2 | 1.158 (4) |
C6B—C11B | 1.395 (4) | C2—S2 | 1.631 (3) |
| | | |
N2—Co—N1 | 121.15 (13) | C7A—C8A—H8A | 120.0 |
N2—Co—N3A | 102.35 (12) | C7B—C8B—C9B | 120.7 (3) |
N1—Co—N3A | 103.56 (11) | C7B—C8B—H8B | 119.7 |
N2—Co—N3B | 103.78 (11) | C9B—C8B—H8B | 119.7 |
N1—Co—N3B | 104.25 (11) | C8A—C9A—C10A | 120.0 (4) |
N3A—Co—N3B | 123.31 (12) | C8A—C9A—H9A | 120.0 |
N3A—C2A—N1A | 109.3 (3) | C10A—C9A—H9A | 120.0 |
N3A—C2A—C6A | 126.6 (3) | C10B—C9B—C8B | 119.5 (3) |
N1A—C2A—C6A | 124.1 (3) | C10B—C9B—H9B | 120.3 |
N3B—C2B—N1B | 109.2 (3) | C8B—C9B—H9B | 120.3 |
N3B—C2B—C6B | 127.5 (3) | C11A—C10A—C9A | 120.8 (3) |
N1B—C2B—C6B | 123.3 (3) | C11A—C10A—H10A | 119.6 |
C5A—C4A—N3A | 109.0 (3) | C9A—C10A—H10A | 119.6 |
C5A—C4A—H4A | 125.5 | C9B—C10B—C11B | 120.1 (3) |
N3A—C4A—H4A | 125.5 | C9B—C10B—H10B | 119.9 |
C5B—C4B—N3B | 109.8 (3) | C11B—C10B—H10B | 119.9 |
C5B—C4B—H4B | 125.1 | C10A—C11A—C6A | 119.2 (4) |
N3B—C4B—H4B | 125.1 | C10A—C11A—H11A | 120.4 |
C4A—C5A—N1A | 106.2 (3) | C6A—C11A—H11A | 120.4 |
C4A—C5A—H5A | 126.9 | C10B—C11B—C6B | 120.5 (3) |
N1A—C5A—H5A | 126.9 | C10B—C11B—H11B | 119.7 |
C4B—C5B—N1B | 106.1 (3) | C6B—C11B—H11B | 119.7 |
C4B—C5B—H5B | 126.9 | C2A—N1A—C5A | 108.6 (3) |
N1B—C5B—H5B | 126.9 | C2A—N1A—H1A | 126 (2) |
C7A—C6A—C11A | 119.1 (3) | C5A—N1A—H1A | 125 (2) |
C7A—C6A—C2A | 120.4 (3) | C2B—N1B—C5B | 108.4 (3) |
C11A—C6A—C2A | 120.3 (3) | C2B—N1B—H1B | 122 (2) |
C7B—C6B—C11B | 119.2 (3) | C5B—N1B—H1B | 130 (2) |
C7B—C6B—C2B | 120.4 (3) | C2A—N3A—C4A | 106.8 (3) |
C11B—C6B—C2B | 120.4 (3) | C2A—N3A—Co | 130.2 (2) |
C8A—C7A—C6A | 120.9 (3) | C4A—N3A—Co | 121.6 (2) |
C8A—C7A—H7A | 119.6 | C2B—N3B—C4B | 106.4 (3) |
C6A—C7A—H7A | 119.6 | C2B—N3B—Co | 131.4 (2) |
C8B—C7B—C6B | 119.9 (3) | C4B—N3B—Co | 121.4 (2) |
C8B—C7B—H7B | 120.0 | C1—N1—Co | 172.1 (3) |
C6B—C7B—H7B | 120.0 | N1—C1—S1 | 178.7 (3) |
C9A—C8A—C7A | 119.9 (4) | C2—N2—Co | 172.0 (3) |
C9A—C8A—H8A | 120.0 | N2—C2—S2 | 179.0 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···S2i | 0.85 (3) | 2.51 (3) | 3.355 (3) | 171 (3) |
N1B—H1B···S1ii | 0.84 (4) | 2.61 (4) | 3.451 (3) | 173 (3) |
Symmetry codes: (i) x−1/2, −y+1, z; (ii) x+1/2, −y+1, z. |
Crystal data top
C38H37CoN9O·2(I) | Dx = 1.626 Mg m−3 |
Mr = 948.49 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pnn2 | Cell parameters from 3415 reflections |
a = 11.3550 (12) Å | θ = 3.2–28.7° |
b = 12.680 (3) Å | µ = 2.08 mm−1 |
c = 13.4516 (14) Å | T = 100 K |
V = 1936.8 (5) Å3 | Prism, red |
Z = 2 | 0.20 × 0.11 × 0.10 mm |
F(000) = 938 | |
Data collection top
Oxford Diffraction SuperNova with Atlas CCD detector diffractometer | 3201 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 3101 reflections with I > 2σ(I) |
Detector resolution: 10.4223 pixels mm-1 | Rint = 0.033 |
ω scans | θmax = 27.0°, θmin = 3.2° |
Absorption correction: multi-scan CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | h = −10→14 |
Tmin = 0.859, Tmax = 1.000 | k = −9→16 |
6159 measured reflections | l = −16→15 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.027 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.065 | w = 1/[σ2(Fo2) + (0.0352P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
3201 reflections | Δρmax = 0.72 e Å−3 |
251 parameters | Δρmin = −0.68 e Å−3 |
16 restraints | Absolute structure: Flack x determined using 964 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.01 (2) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Co | 0.5000 | 0.5000 | 0.54738 (7) | 0.0145 (2) | |
I | 0.52089 (2) | 0.68918 (2) | 0.88794 (3) | 0.02375 (10) | |
C2A | 0.3291 (4) | 0.6733 (4) | 0.4875 (4) | 0.0194 (10) | |
H2A | 0.2967 | 0.6276 | 0.4409 | 0.023* | |
C2B | 0.7337 (4) | 0.6137 (4) | 0.4862 (4) | 0.0198 (10) | |
H2B | 0.7100 | 0.6226 | 0.4206 | 0.024* | |
C4A | 0.4361 (4) | 0.7380 (4) | 0.6031 (3) | 0.0180 (9) | |
H4A | 0.4942 | 0.7443 | 0.6515 | 0.022* | |
C4B | 0.7356 (4) | 0.5735 (4) | 0.6418 (3) | 0.0188 (9) | |
H4B | 0.7118 | 0.5480 | 0.7034 | 0.023* | |
C5A | 0.3564 (4) | 0.8138 (4) | 0.5806 (4) | 0.0186 (10) | |
C5B | 0.8416 (4) | 0.6185 (4) | 0.6228 (3) | 0.0180 (10) | |
C6A | 0.3348 (4) | 0.9197 (4) | 0.6201 (4) | 0.0203 (10) | |
C6B | 0.9423 (4) | 0.6363 (4) | 0.6870 (3) | 0.0193 (10) | |
C7A | 0.2883 (4) | 0.9995 (4) | 0.5620 (4) | 0.0280 (12) | |
H7A | 0.2696 | 0.9858 | 0.4959 | 0.034* | |
C7B | 1.0549 (4) | 0.6521 (5) | 0.6494 (4) | 0.0268 (11) | |
H7B | 1.0666 | 0.6546 | 0.5811 | 0.032* | |
C8A | 0.2689 (5) | 1.0991 (4) | 0.6000 (4) | 0.0334 (13) | |
H8A | 0.2373 | 1.1518 | 0.5600 | 0.040* | |
C8B | 1.1496 (4) | 0.6640 (5) | 0.7132 (4) | 0.0291 (12) | |
H8B | 1.2250 | 0.6726 | 0.6873 | 0.035* | |
C9A | 0.2971 (4) | 1.1200 (4) | 0.6990 (4) | 0.0298 (12) | |
H9A | 0.2849 | 1.1869 | 0.7254 | 0.036* | |
C9B | 1.1331 (4) | 0.6633 (5) | 0.8147 (4) | 0.0298 (12) | |
H9B | 1.1967 | 0.6733 | 0.8573 | 0.036* | |
C10A | 0.3432 (4) | 1.0411 (5) | 0.7571 (4) | 0.0296 (12) | |
H10A | 0.3622 | 1.0552 | 0.8230 | 0.035* | |
C10B | 1.0223 (4) | 0.6479 (6) | 0.8525 (5) | 0.0403 (17) | |
H10B | 1.0112 | 0.6455 | 0.9209 | 0.048* | |
C11A | 0.3616 (4) | 0.9410 (4) | 0.7195 (4) | 0.0255 (11) | |
H11A | 0.3918 | 0.8881 | 0.7601 | 0.031* | |
C11B | 0.9274 (4) | 0.6357 (5) | 0.7897 (4) | 0.0343 (14) | |
H11B | 0.8524 | 0.6270 | 0.8162 | 0.041* | |
N1A | 0.2893 (3) | 0.7714 (3) | 0.5050 (3) | 0.0208 (8) | |
H1A | 0.229 (4) | 0.798 (4) | 0.476 (4) | 0.031* | |
N1B | 0.8393 (3) | 0.6425 (3) | 0.5223 (3) | 0.0196 (8) | |
H1B | 0.896 (3) | 0.674 (4) | 0.493 (4) | 0.029* | |
N3A | 0.4192 (3) | 0.6500 (3) | 0.5445 (3) | 0.0174 (8) | |
N3B | 0.6680 (3) | 0.5710 (3) | 0.5566 (3) | 0.0175 (8) | |
O1 | 0.5000 | 0.5000 | 0.7070 (4) | 0.0183 (10) | |
H1 | 0.498 (5) | 0.552 (3) | 0.744 (4) | 0.027* | |
N1 | 0.5000 | 0.5000 | 0.3865 (6) | 0.0240 (12) | |
C12 | 0.506 (2) | 0.5201 (10) | 0.3025 (7) | 0.020 (4) | 0.5 |
C13 | 0.5101 (13) | 0.5390 (14) | 0.1980 (10) | 0.046 (4) | 0.5 |
H13A | 0.5907 | 0.5405 | 0.1764 | 0.069* | 0.5 |
H13B | 0.4736 | 0.6055 | 0.1835 | 0.069* | 0.5 |
H13C | 0.4690 | 0.4837 | 0.1637 | 0.069* | 0.5 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co | 0.0139 (3) | 0.0158 (5) | 0.0137 (4) | −0.0006 (4) | 0.000 | 0.000 |
I | 0.02090 (14) | 0.03002 (19) | 0.02032 (16) | 0.00471 (11) | −0.00410 (17) | −0.00928 (17) |
C2A | 0.019 (2) | 0.020 (2) | 0.020 (2) | 0.001 (2) | −0.0031 (18) | −0.001 (2) |
C2B | 0.018 (2) | 0.020 (2) | 0.021 (2) | −0.001 (2) | 0.0017 (17) | −0.001 (2) |
C4A | 0.0156 (18) | 0.022 (2) | 0.017 (2) | −0.002 (2) | −0.0007 (17) | 0.001 (2) |
C4B | 0.0167 (19) | 0.023 (2) | 0.016 (2) | −0.002 (2) | −0.0013 (16) | 0.001 (2) |
C5A | 0.0149 (19) | 0.022 (2) | 0.019 (2) | −0.0009 (19) | 0.0020 (17) | 0.0035 (19) |
C5B | 0.0141 (19) | 0.018 (2) | 0.022 (2) | 0.000 (2) | 0.0014 (18) | −0.001 (2) |
C6A | 0.0147 (19) | 0.020 (2) | 0.026 (3) | 0.003 (2) | 0.0022 (18) | 0.000 (2) |
C6B | 0.0138 (18) | 0.022 (2) | 0.022 (2) | −0.003 (2) | 0.0004 (18) | −0.002 (2) |
C7A | 0.034 (2) | 0.023 (3) | 0.026 (3) | 0.005 (2) | 0.003 (2) | 0.003 (2) |
C7B | 0.020 (2) | 0.034 (3) | 0.026 (3) | −0.004 (2) | 0.003 (2) | 0.006 (2) |
C8A | 0.038 (3) | 0.023 (3) | 0.039 (3) | 0.007 (3) | 0.008 (3) | 0.007 (3) |
C8B | 0.016 (2) | 0.039 (3) | 0.032 (3) | −0.006 (2) | −0.001 (2) | 0.010 (3) |
C9A | 0.026 (2) | 0.021 (3) | 0.042 (3) | 0.001 (2) | 0.010 (2) | −0.007 (3) |
C9B | 0.020 (2) | 0.038 (3) | 0.031 (3) | −0.001 (2) | −0.006 (2) | −0.005 (3) |
C10A | 0.020 (2) | 0.034 (3) | 0.035 (3) | −0.001 (2) | 0.002 (2) | −0.007 (3) |
C10B | 0.023 (3) | 0.078 (5) | 0.021 (3) | −0.003 (3) | 0.0000 (19) | −0.014 (3) |
C11A | 0.019 (2) | 0.028 (3) | 0.030 (3) | 0.001 (2) | −0.001 (2) | −0.001 (2) |
C11B | 0.017 (2) | 0.062 (4) | 0.025 (3) | −0.003 (3) | 0.005 (2) | −0.008 (3) |
N1A | 0.0156 (17) | 0.025 (2) | 0.021 (2) | 0.0019 (18) | −0.0049 (15) | 0.0039 (19) |
N1B | 0.0159 (16) | 0.024 (2) | 0.0185 (19) | −0.0032 (17) | 0.0018 (14) | 0.0021 (18) |
N3A | 0.0147 (14) | 0.0175 (19) | 0.0200 (19) | −0.0017 (16) | 0.0002 (15) | 0.0026 (17) |
N3B | 0.0139 (14) | 0.021 (2) | 0.0178 (18) | 0.0008 (16) | −0.0013 (14) | 0.0009 (18) |
O1 | 0.025 (2) | 0.015 (3) | 0.015 (3) | −0.004 (2) | 0.000 | 0.000 |
N1 | 0.023 (2) | 0.028 (3) | 0.021 (3) | 0.001 (2) | 0.000 | 0.000 |
C12 | 0.014 (5) | 0.020 (11) | 0.024 (5) | −0.001 (9) | 0.003 (5) | −0.002 (4) |
C13 | 0.030 (5) | 0.068 (10) | 0.039 (7) | 0.015 (7) | 0.001 (5) | −0.004 (7) |
Geometric parameters (Å, º) top
Co—N3Ai | 2.112 (4) | C7B—C8B | 1.384 (7) |
Co—N3A | 2.113 (4) | C7B—H7B | 0.9300 |
Co—N3B | 2.113 (3) | C8A—C9A | 1.395 (8) |
Co—N3Bi | 2.113 (3) | C8A—H8A | 0.9300 |
Co—O1 | 2.148 (5) | C8B—C9B | 1.379 (7) |
Co—N1 | 2.163 (9) | C8B—H8B | 0.9300 |
C2A—N3A | 1.312 (6) | C9A—C10A | 1.373 (8) |
C2A—N1A | 1.344 (6) | C9A—H9A | 0.9300 |
C2A—H2A | 0.9300 | C9B—C10B | 1.371 (7) |
C2B—N3B | 1.322 (6) | C9B—H9B | 0.9300 |
C2B—N1B | 1.344 (6) | C10A—C11A | 1.383 (8) |
C2B—H2B | 0.9300 | C10A—H10A | 0.9300 |
C4A—C5A | 1.355 (6) | C10B—C11B | 1.379 (7) |
C4A—N3A | 1.378 (6) | C10B—H10B | 0.9300 |
C4A—H4A | 0.9300 | C11A—H11A | 0.9300 |
C4B—C5B | 1.356 (6) | C11B—H11B | 0.9300 |
C4B—N3B | 1.379 (5) | N1A—H1A | 0.85 (2) |
C4B—H4B | 0.9300 | N1B—H1B | 0.853 (13) |
C5A—N1A | 1.379 (6) | O1—H1 | 0.829 (13) |
C5A—C6A | 1.465 (6) | N1—C12i | 1.161 (12) |
C5B—N1B | 1.386 (6) | N1—C12 | 1.161 (12) |
C5B—C6B | 1.451 (6) | C12—C12i | 0.53 (2) |
C6A—C7A | 1.383 (7) | C12—C13 | 1.427 (16) |
C6A—C11A | 1.397 (7) | C12—C13i | 1.603 (17) |
C6B—C7B | 1.389 (6) | C13—H13A | 0.9600 |
C6B—C11B | 1.391 (7) | C13—H13B | 0.9600 |
C7A—C8A | 1.380 (7) | C13—H13C | 0.9600 |
C7A—H7A | 0.9300 | | |
| | | |
N3Ai—Co—N3A | 177.9 (2) | C9B—C8B—C7B | 120.5 (5) |
N3Ai—Co—N3B | 89.57 (13) | C9B—C8B—H8B | 119.8 |
N3A—Co—N3B | 90.55 (13) | C7B—C8B—H8B | 119.8 |
N3Ai—Co—N3Bi | 90.55 (13) | C10A—C9A—C8A | 119.5 (5) |
N3A—Co—N3Bi | 89.57 (13) | C10A—C9A—H9A | 120.3 |
N3B—Co—N3Bi | 173.2 (2) | C8A—C9A—H9A | 120.3 |
N3Ai—Co—O1 | 91.03 (11) | C10B—C9B—C8B | 119.5 (5) |
N3A—Co—O1 | 91.03 (11) | C10B—C9B—H9B | 120.2 |
N3B—Co—O1 | 86.62 (11) | C8B—C9B—H9B | 120.2 |
N3Bi—Co—O1 | 86.62 (11) | C9A—C10A—C11A | 121.2 (5) |
N3Ai—Co—N1 | 88.97 (11) | C9A—C10A—H10A | 119.4 |
N3A—Co—N1 | 88.97 (11) | C11A—C10A—H10A | 119.4 |
N3B—Co—N1 | 93.38 (11) | C9B—C10B—C11B | 120.4 (6) |
N3Bi—Co—N1 | 93.38 (11) | C9B—C10B—H10B | 119.8 |
O1—Co—N1 | 180.0 | C11B—C10B—H10B | 119.8 |
N3A—C2A—N1A | 111.6 (4) | C10A—C11A—C6A | 119.7 (5) |
N3A—C2A—H2A | 124.2 | C10A—C11A—H11A | 120.2 |
N1A—C2A—H2A | 124.2 | C6A—C11A—H11A | 120.2 |
N3B—C2B—N1B | 110.9 (4) | C10B—C11B—C6B | 120.8 (5) |
N3B—C2B—H2B | 124.6 | C10B—C11B—H11B | 119.6 |
N1B—C2B—H2B | 124.6 | C6B—C11B—H11B | 119.6 |
C5A—C4A—N3A | 110.7 (4) | C2A—N1A—C5A | 107.7 (4) |
C5A—C4A—H4A | 124.6 | C2A—N1A—H1A | 123 (4) |
N3A—C4A—H4A | 124.6 | C5A—N1A—H1A | 129 (4) |
C5B—C4B—N3B | 110.3 (4) | C2B—N1B—C5B | 108.0 (4) |
C5B—C4B—H4B | 124.8 | C2B—N1B—H1B | 130 (4) |
N3B—C4B—H4B | 124.8 | C5B—N1B—H1B | 122 (4) |
C4A—C5A—N1A | 104.9 (4) | C2A—N3A—C4A | 105.1 (4) |
C4A—C5A—C6A | 133.0 (5) | C2A—N3A—Co | 123.5 (3) |
N1A—C5A—C6A | 122.1 (4) | C4A—N3A—Co | 131.1 (3) |
C4B—C5B—N1B | 105.0 (4) | C2B—N3B—C4B | 105.8 (4) |
C4B—C5B—C6B | 130.8 (4) | C2B—N3B—Co | 129.9 (3) |
N1B—C5B—C6B | 124.1 (4) | C4B—N3B—Co | 124.1 (3) |
C7A—C6A—C11A | 118.8 (5) | Co—O1—H1 | 127 (5) |
C7A—C6A—C5A | 122.0 (5) | C12i—N1—Co | 166.9 (6) |
C11A—C6A—C5A | 119.2 (5) | C12—N1—Co | 166.9 (6) |
C7B—C6B—C11B | 118.3 (4) | C12i—C12—N1 | 76.9 (6) |
C7B—C6B—C5B | 122.1 (4) | C12i—C12—C13 | 99.9 (8) |
C11B—C6B—C5B | 119.6 (4) | N1—C12—C13 | 176.7 (13) |
C8A—C7A—C6A | 121.4 (6) | C12i—C12—C13i | 61.3 (7) |
C8A—C7A—H7A | 119.3 | N1—C12—C13i | 138.2 (11) |
C6A—C7A—H7A | 119.3 | C12—C13—H13A | 109.5 |
C8B—C7B—C6B | 120.4 (5) | C12—C13—H13B | 109.5 |
C8B—C7B—H7B | 119.8 | H13A—C13—H13B | 109.5 |
C6B—C7B—H7B | 119.8 | C12—C13—H13C | 109.5 |
C7A—C8A—C9A | 119.4 (5) | H13A—C13—H13C | 109.5 |
C7A—C8A—H8A | 120.3 | H13B—C13—H13C | 109.5 |
C9A—C8A—H8A | 120.3 | | |
Symmetry code: (i) −x+1, −y+1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···Iii | 0.86 (5) | 2.65 (5) | 3.467 (4) | 160 (4) |
N1B—H1B···Iii | 0.85 (4) | 2.65 (5) | 3.475 (4) | 163 (4) |
O1—H1···I | 0.83 (5) | 2.62 (5) | 3.426 (4) | 167 (4) |
Symmetry code: (ii) x−1/2, −y+3/2, z−1/2. |
Crystal data top
C38H37CoN9O·2(NO3) | Dx = 1.403 Mg m−3 |
Mr = 818.71 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pnn2 | Cell parameters from 3240 reflections |
a = 11.3655 (6) Å | θ = 4.4–28.9° |
b = 12.5153 (7) Å | µ = 0.51 mm−1 |
c = 13.6247 (6) Å | T = 100 K |
V = 1938.01 (17) Å3 | Prism, purple |
Z = 2 | 0.20 × 0.12 × 0.12 mm |
F(000) = 850 | |
Data collection top
Oxford Diffraction SuperNova with Atlas CCD detector diffractometer | 3470 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 3354 reflections with I > 2σ(I) |
Detector resolution: 10.4223 pixels mm-1 | Rint = 0.026 |
ω scans | θmax = 27.0°, θmin = 3.0° |
Absorption correction: multi-scan CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | h = −8→14 |
Tmin = 0.853, Tmax = 1.000 | k = −15→14 |
6658 measured reflections | l = −17→17 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.027 | w = 1/[σ2(Fo2) + (0.033P)2 + 0.7309P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.072 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.32 e Å−3 |
3470 reflections | Δρmin = −0.23 e Å−3 |
279 parameters | Absolute structure: Refined as an inversion twin. |
10 restraints | Absolute structure parameter: 0.178 (17) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component inversion twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Co | 0.5000 | 0.0000 | 0.29392 (4) | 0.01557 (12) | |
N1A | 0.1533 (2) | 0.13514 (19) | 0.32243 (16) | 0.0197 (5) | |
H1A | 0.102 (3) | 0.163 (3) | 0.359 (2) | 0.029* | |
C2A | 0.2608 (3) | 0.1076 (2) | 0.3574 (2) | 0.0221 (6) | |
H2A | 0.2824 | 0.1116 | 0.4231 | 0.026* | |
N3A | 0.33061 (17) | 0.07466 (15) | 0.28666 (18) | 0.0190 (4) | |
C4A | 0.2646 (2) | 0.0826 (2) | 0.2022 (2) | 0.0213 (6) | |
H4A | 0.2919 | 0.0650 | 0.1399 | 0.026* | |
C5A | 0.1546 (2) | 0.1193 (2) | 0.2215 (2) | 0.0194 (5) | |
C6A | 0.0544 (2) | 0.1385 (2) | 0.1565 (2) | 0.0208 (5) | |
C7A | −0.0603 (3) | 0.1499 (3) | 0.1911 (2) | 0.0340 (7) | |
H7A | −0.0747 | 0.1480 | 0.2582 | 0.041* | |
C8A | −0.1534 (3) | 0.1640 (3) | 0.1262 (3) | 0.0344 (7) | |
H8A | −0.2294 | 0.1722 | 0.1503 | 0.041* | |
C9A | −0.1337 (3) | 0.1660 (3) | 0.0267 (3) | 0.0317 (7) | |
H9A | −0.1960 | 0.1755 | −0.0167 | 0.038* | |
C10A | −0.0210 (3) | 0.1539 (4) | −0.0079 (2) | 0.0461 (10) | |
H10A | −0.0073 | 0.1549 | −0.0752 | 0.055* | |
C11A | 0.0718 (3) | 0.1402 (3) | 0.0558 (2) | 0.0383 (8) | |
H11A | 0.1475 | 0.1320 | 0.0308 | 0.046* | |
N1B | 0.7095 (2) | 0.27619 (19) | 0.33912 (18) | 0.0224 (5) | |
H1B | 0.766 (2) | 0.303 (3) | 0.370 (2) | 0.034* | |
C2B | 0.6716 (2) | 0.1766 (2) | 0.3566 (2) | 0.0222 (6) | |
H2B | 0.7032 | 0.1315 | 0.4041 | 0.027* | |
N3B | 0.58371 (17) | 0.15045 (15) | 0.29784 (19) | 0.0182 (4) | |
C4B | 0.5650 (2) | 0.2393 (2) | 0.2396 (2) | 0.0196 (5) | |
H4B | 0.5077 | 0.2447 | 0.1911 | 0.023* | |
C5B | 0.6429 (2) | 0.3178 (2) | 0.26387 (19) | 0.0192 (5) | |
C6B | 0.6633 (2) | 0.4243 (2) | 0.2216 (2) | 0.0227 (5) | |
C7B | 0.7044 (3) | 0.5090 (2) | 0.2783 (2) | 0.0317 (7) | |
H7B | 0.7198 | 0.4988 | 0.3447 | 0.038* | |
C8B | 0.7224 (3) | 0.6087 (2) | 0.2360 (3) | 0.0399 (8) | |
H8B | 0.7501 | 0.6649 | 0.2742 | 0.048* | |
C9B | 0.6995 (3) | 0.6247 (3) | 0.1378 (3) | 0.0355 (8) | |
H9B | 0.7116 | 0.6915 | 0.1098 | 0.043* | |
C10B | 0.6586 (3) | 0.5410 (3) | 0.0809 (3) | 0.0341 (7) | |
H10B | 0.6424 | 0.5519 | 0.0147 | 0.041* | |
C11B | 0.6416 (3) | 0.4409 (2) | 0.1225 (2) | 0.0280 (6) | |
H11B | 0.6155 | 0.3846 | 0.0837 | 0.034* | |
O1 | 0.5000 | 0.0000 | 0.1352 (3) | 0.0223 (8) | |
H1 | 0.480 (3) | −0.050 (2) | 0.100 (3) | 0.034* | |
N1 | 0.5000 | 0.0000 | 0.4543 (3) | 0.0248 (10) | |
C12 | 0.496 (2) | 0.0187 (9) | 0.5362 (4) | 0.027 (3) | 0.5 |
C13 | 0.4917 (9) | 0.0380 (7) | 0.6421 (5) | 0.051 (3) | 0.5 |
H13A | 0.4173 | 0.0140 | 0.6673 | 0.076* | 0.5 |
H13B | 0.5005 | 0.1130 | 0.6547 | 0.076* | 0.5 |
H13C | 0.5541 | −0.0005 | 0.6737 | 0.076* | 0.5 |
N2 | 0.4680 (2) | 0.1961 (2) | −0.03418 (18) | 0.0248 (5) | |
O2 | 0.56214 (19) | 0.1728 (2) | 0.00745 (17) | 0.0369 (5) | |
O3 | 0.45595 (19) | 0.28495 (17) | −0.07561 (16) | 0.0319 (5) | |
O4 | 0.38331 (19) | 0.13228 (18) | −0.03354 (19) | 0.0400 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co | 0.0135 (2) | 0.0151 (2) | 0.0180 (2) | 0.00016 (18) | 0.000 | 0.000 |
N1A | 0.0153 (10) | 0.0233 (11) | 0.0204 (11) | 0.0044 (9) | 0.0015 (9) | −0.0025 (9) |
C2A | 0.0223 (13) | 0.0236 (14) | 0.0202 (12) | 0.0010 (11) | −0.0004 (12) | −0.0015 (10) |
N3A | 0.0167 (9) | 0.0180 (9) | 0.0222 (10) | 0.0003 (8) | −0.0009 (12) | −0.0007 (10) |
C4A | 0.0170 (13) | 0.0256 (14) | 0.0215 (12) | 0.0008 (11) | 0.0000 (12) | 0.0001 (10) |
C5A | 0.0187 (13) | 0.0180 (12) | 0.0215 (12) | −0.0002 (10) | 0.0000 (12) | 0.0010 (11) |
C6A | 0.0160 (13) | 0.0200 (13) | 0.0263 (13) | −0.0004 (11) | −0.0007 (12) | −0.0011 (10) |
C7A | 0.0214 (15) | 0.051 (2) | 0.0291 (15) | 0.0078 (15) | 0.0011 (13) | −0.0082 (14) |
C8A | 0.0199 (14) | 0.0449 (18) | 0.0385 (16) | 0.0089 (14) | −0.0013 (14) | −0.0102 (15) |
C9A | 0.0209 (14) | 0.0388 (17) | 0.0354 (15) | 0.0005 (13) | −0.0076 (14) | 0.0069 (14) |
C10A | 0.0256 (15) | 0.087 (3) | 0.0260 (16) | −0.0017 (19) | −0.0013 (15) | 0.0146 (18) |
C11A | 0.0170 (14) | 0.070 (2) | 0.0283 (15) | 0.0013 (15) | 0.0053 (14) | 0.0074 (16) |
N1B | 0.0182 (10) | 0.0216 (11) | 0.0274 (11) | −0.0035 (9) | −0.0036 (10) | −0.0031 (9) |
C2B | 0.0201 (13) | 0.0199 (13) | 0.0268 (13) | 0.0013 (11) | −0.0028 (12) | 0.0018 (11) |
N3B | 0.0147 (9) | 0.0180 (9) | 0.0217 (10) | −0.0007 (8) | −0.0015 (11) | 0.0011 (10) |
C4B | 0.0173 (11) | 0.0187 (12) | 0.0227 (12) | 0.0018 (10) | 0.0003 (11) | −0.0005 (10) |
C5B | 0.0164 (12) | 0.0186 (12) | 0.0225 (12) | 0.0013 (10) | 0.0017 (11) | −0.0006 (10) |
C6B | 0.0191 (12) | 0.0172 (12) | 0.0317 (13) | 0.0001 (10) | 0.0067 (13) | −0.0008 (11) |
C7B | 0.0402 (16) | 0.0226 (13) | 0.0322 (19) | −0.0054 (12) | 0.0054 (15) | −0.0030 (12) |
C8B | 0.048 (2) | 0.0204 (14) | 0.051 (2) | −0.0072 (14) | 0.0115 (19) | −0.0090 (14) |
C9B | 0.0349 (17) | 0.0237 (15) | 0.0480 (19) | −0.0002 (13) | 0.0133 (16) | 0.0089 (13) |
C10B | 0.0307 (16) | 0.0326 (16) | 0.0391 (17) | 0.0001 (13) | 0.0063 (15) | 0.0101 (14) |
C11B | 0.0247 (14) | 0.0248 (14) | 0.0345 (15) | −0.0016 (12) | 0.0018 (14) | 0.0025 (12) |
O1 | 0.0227 (18) | 0.024 (2) | 0.0201 (17) | 0.0036 (12) | 0.000 | 0.000 |
N1 | 0.024 (2) | 0.028 (2) | 0.022 (2) | −0.0036 (14) | 0.000 | 0.000 |
C12 | 0.021 (4) | 0.032 (10) | 0.027 (2) | −0.010 (9) | −0.001 (4) | −0.003 (3) |
C13 | 0.044 (4) | 0.083 (7) | 0.024 (3) | −0.020 (6) | −0.002 (4) | −0.009 (3) |
N2 | 0.0223 (11) | 0.0323 (13) | 0.0198 (10) | −0.0005 (11) | −0.0003 (11) | 0.0024 (10) |
O2 | 0.0235 (11) | 0.0487 (14) | 0.0384 (12) | −0.0037 (10) | −0.0136 (10) | 0.0098 (10) |
O3 | 0.0290 (10) | 0.0324 (12) | 0.0344 (11) | −0.0022 (9) | 0.0029 (10) | 0.0121 (10) |
O4 | 0.0254 (10) | 0.0401 (13) | 0.0543 (14) | −0.0111 (10) | −0.0127 (12) | 0.0207 (11) |
Geometric parameters (Å, º) top
Co—N3Bi | 2.1103 (19) | N1B—H1B | 0.84 (2) |
Co—N3B | 2.1103 (19) | C2B—N3B | 1.321 (3) |
Co—N3A | 2.1423 (19) | C2B—H2B | 0.9300 |
Co—N3Ai | 2.1423 (19) | N3B—C4B | 1.382 (3) |
Co—O1 | 2.163 (3) | C4B—C5B | 1.363 (4) |
Co—N1 | 2.186 (4) | C4B—H4B | 0.9300 |
N1A—C2A | 1.356 (4) | C5B—C6B | 1.471 (4) |
N1A—C5A | 1.390 (4) | C6B—C11B | 1.388 (4) |
N1A—H1A | 0.84 (2) | C6B—C7B | 1.393 (4) |
C2A—N3A | 1.315 (4) | C7B—C8B | 1.390 (4) |
C2A—H2A | 0.9300 | C7B—H7B | 0.9300 |
N3A—C4A | 1.378 (4) | C8B—C9B | 1.378 (5) |
C4A—C5A | 1.358 (4) | C8B—H8B | 0.9300 |
C4A—H4A | 0.9300 | C9B—C10B | 1.383 (5) |
C5A—C6A | 1.462 (4) | C9B—H9B | 0.9300 |
C6A—C11A | 1.386 (4) | C10B—C11B | 1.389 (4) |
C6A—C7A | 1.394 (4) | C10B—H10B | 0.9300 |
C7A—C8A | 1.390 (5) | C11B—H11B | 0.9300 |
C7A—H7A | 0.9300 | O1—H1 | 0.82 (2) |
C8A—C9A | 1.374 (5) | N1—C12 | 1.140 (8) |
C8A—H8A | 0.9300 | C12—C13 | 1.464 (9) |
C9A—C10A | 1.373 (4) | C13—H13A | 0.9600 |
C9A—H9A | 0.9300 | C13—H13B | 0.9600 |
C10A—C11A | 1.377 (5) | C13—H13C | 0.9600 |
C10A—H10A | 0.9300 | N2—O2 | 1.246 (3) |
C11A—H11A | 0.9300 | N2—O4 | 1.251 (3) |
N1B—C2B | 1.340 (4) | N2—O3 | 1.254 (3) |
N1B—C5B | 1.377 (3) | | |
| | | |
N3Bi—Co—N3B | 177.10 (15) | C6A—C11A—H11A | 119.5 |
N3Bi—Co—N3A | 89.15 (7) | C2B—N1B—C5B | 107.9 (2) |
N3B—Co—N3A | 90.99 (7) | C2B—N1B—H1B | 122 (2) |
N3Bi—Co—N3Ai | 90.99 (7) | C5B—N1B—H1B | 130 (2) |
N3B—Co—N3Ai | 89.15 (7) | N3B—C2B—N1B | 111.4 (2) |
N3A—Co—N3Ai | 174.71 (14) | N3B—C2B—H2B | 124.3 |
N3Bi—Co—O1 | 91.45 (7) | N1B—C2B—H2B | 124.3 |
N3B—Co—O1 | 91.45 (7) | C2B—N3B—C4B | 105.4 (2) |
N3A—Co—O1 | 87.35 (7) | C2B—N3B—Co | 125.24 (18) |
N3Ai—Co—O1 | 87.35 (7) | C4B—N3B—Co | 129.32 (18) |
N3Bi—Co—N1 | 88.55 (7) | C5B—C4B—N3B | 109.9 (2) |
N3B—Co—N1 | 88.55 (7) | C5B—C4B—H4B | 125.0 |
N3A—Co—N1 | 92.65 (7) | N3B—C4B—H4B | 125.0 |
N3Ai—Co—N1 | 92.65 (7) | C4B—C5B—N1B | 105.4 (2) |
O1—Co—N1 | 180.0 | C4B—C5B—C6B | 131.4 (3) |
C2A—N1A—C5A | 107.6 (2) | N1B—C5B—C6B | 123.2 (2) |
C2A—N1A—H1A | 121 (2) | C11B—C6B—C7B | 119.0 (3) |
C5A—N1A—H1A | 131 (2) | C11B—C6B—C5B | 119.3 (3) |
N3A—C2A—N1A | 111.5 (2) | C7B—C6B—C5B | 121.7 (3) |
N3A—C2A—H2A | 124.3 | C8B—C7B—C6B | 120.1 (3) |
N1A—C2A—H2A | 124.3 | C8B—C7B—H7B | 119.9 |
C2A—N3A—C4A | 105.1 (2) | C6B—C7B—H7B | 119.9 |
C2A—N3A—Co | 130.2 (2) | C9B—C8B—C7B | 120.4 (3) |
C4A—N3A—Co | 124.01 (18) | C9B—C8B—H8B | 119.8 |
C5A—C4A—N3A | 111.4 (2) | C7B—C8B—H8B | 119.8 |
C5A—C4A—H4A | 124.3 | C8B—C9B—C10B | 119.9 (3) |
N3A—C4A—H4A | 124.3 | C8B—C9B—H9B | 120.1 |
C4A—C5A—N1A | 104.5 (2) | C10B—C9B—H9B | 120.1 |
C4A—C5A—C6A | 131.0 (3) | C9B—C10B—C11B | 120.0 (3) |
N1A—C5A—C6A | 124.6 (3) | C9B—C10B—H10B | 120.0 |
C11A—C6A—C7A | 117.8 (3) | C11B—C10B—H10B | 120.0 |
C11A—C6A—C5A | 119.4 (3) | C6B—C11B—C10B | 120.5 (3) |
C7A—C6A—C5A | 122.7 (3) | C6B—C11B—H11B | 119.7 |
C8A—C7A—C6A | 120.7 (3) | C10B—C11B—H11B | 119.7 |
C8A—C7A—H7A | 119.7 | Co—O1—H1 | 125 (3) |
C6A—C7A—H7A | 119.7 | C12—N1—Co | 168.0 (6) |
C9A—C8A—C7A | 120.3 (3) | N1—C12—C13 | 177.6 (10) |
C9A—C8A—H8A | 119.8 | C12—C13—H13A | 109.5 |
C7A—C8A—H8A | 119.8 | C12—C13—H13B | 109.5 |
C10A—C9A—C8A | 119.3 (3) | H13A—C13—H13B | 109.5 |
C10A—C9A—H9A | 120.4 | C12—C13—H13C | 109.5 |
C8A—C9A—H9A | 120.4 | H13A—C13—H13C | 109.5 |
C9A—C10A—C11A | 120.8 (3) | H13B—C13—H13C | 109.5 |
C9A—C10A—H10A | 119.6 | O2—N2—O4 | 120.5 (2) |
C11A—C10A—H10A | 119.6 | O2—N2—O3 | 120.4 (2) |
C10A—C11A—C6A | 121.1 (3) | O4—N2—O3 | 119.0 (2) |
C10A—C11A—H11A | 119.5 | | |
Symmetry code: (i) −x+1, −y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O3ii | 0.84 (3) | 2.00 (3) | 2.821 (3) | 167 (3) |
N1B—H1B···O3iii | 0.84 (3) | 2.53 (3) | 3.127 (3) | 128 (3) |
N1B—H1B···O4iii | 0.84 (3) | 2.03 (3) | 2.868 (3) | 170 (3) |
O1—H1···O2i | 0.82 (3) | 2.05 (3) | 2.865 (3) | 177 (3) |
Symmetry codes: (i) −x+1, −y, z; (ii) x−1/2, −y+1/2, z+1/2; (iii) x+1/2, −y+1/2, z+1/2. |
Crystal data top
C38H32CoN10S2·2(CH4O) | Z = 1 |
Mr = 815.87 | F(000) = 425 |
Triclinic, P1 | Dx = 1.320 Mg m−3 |
a = 8.6822 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.4570 (9) Å | Cell parameters from 3225 reflections |
c = 13.6578 (12) Å | θ = 4.3–29.6° |
α = 103.023 (8)° | µ = 0.57 mm−1 |
β = 95.901 (7)° | T = 100 K |
γ = 107.217 (8)° | Prism, orange |
V = 1026.15 (17) Å3 | 0.24 × 0.15 × 0.14 mm |
Data collection top
Oxford Diffraction SuperNova with Atlas CCD detector diffractometer | 4241 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 3549 reflections with I > 2σ(I) |
Detector resolution: 10.4223 pixels mm-1 | Rint = 0.032 |
ω scans | θmax = 26.5°, θmin = 2.8° |
Absorption correction: multi-scan CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | h = −10→10 |
Tmin = 0.780, Tmax = 1.000 | k = −11→9 |
8705 measured reflections | l = −16→17 |
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)] = 0.039 | Hydrogen site location: mixed |
wR(F2) = 0.093 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0309P)2 + 0.5771P] where P = (Fo2 + 2Fc2)/3 |
4241 reflections | (Δ/σ)max < 0.001 |
260 parameters | Δρmax = 0.28 e Å−3 |
3 restraints | Δρmin = −0.38 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Co | 0.5000 | 0.0000 | 0.0000 | 0.01496 (11) | |
N1A | 0.8245 (2) | 0.1512 (2) | 0.28699 (13) | 0.0206 (4) | |
H1A | 0.9216 (16) | 0.186 (3) | 0.3232 (16) | 0.031* | |
C2A | 0.7864 (2) | 0.1130 (2) | 0.18446 (15) | 0.0186 (4) | |
H2A | 0.8630 | 0.1182 | 0.1414 | 0.022* | |
N3A | 0.62656 (19) | 0.06713 (18) | 0.15296 (12) | 0.0175 (4) | |
C4A | 0.5598 (2) | 0.0779 (2) | 0.24040 (15) | 0.0190 (4) | |
H4A | 0.4483 | 0.0530 | 0.2418 | 0.023* | |
C5A | 0.6804 (2) | 0.1303 (2) | 0.32429 (15) | 0.0192 (4) | |
C6A | 0.6744 (3) | 0.1620 (2) | 0.43391 (16) | 0.0238 (5) | |
C7A | 0.8039 (3) | 0.1675 (3) | 0.50515 (17) | 0.0322 (6) | |
H7A | 0.8972 | 0.1516 | 0.4838 | 0.039* | |
C8A | 0.7939 (3) | 0.1967 (3) | 0.60824 (18) | 0.0416 (7) | |
H8A | 0.8815 | 0.2019 | 0.6559 | 0.050* | |
C9A | 0.6552 (3) | 0.2181 (3) | 0.64033 (18) | 0.0413 (7) | |
H9A | 0.6493 | 0.2375 | 0.7094 | 0.050* | |
C10A | 0.5255 (3) | 0.2106 (3) | 0.57024 (18) | 0.0354 (6) | |
H10A | 0.4315 | 0.2241 | 0.5920 | 0.042* | |
C11A | 0.5343 (3) | 0.1830 (3) | 0.46733 (16) | 0.0275 (5) | |
H11A | 0.4464 | 0.1786 | 0.4203 | 0.033* | |
N1B | 0.7994 (2) | 0.3840 (2) | −0.08532 (13) | 0.0202 (4) | |
H1B | 0.809 (3) | 0.4694 (17) | −0.0993 (18) | 0.030* | |
C2B | 0.6720 (2) | 0.3065 (2) | −0.04877 (15) | 0.0203 (4) | |
H2B | 0.5855 | 0.3410 | −0.0328 | 0.024* | |
N3B | 0.68554 (19) | 0.17517 (19) | −0.03846 (12) | 0.0179 (4) | |
C4B | 0.8302 (2) | 0.1702 (2) | −0.07021 (15) | 0.0185 (4) | |
H4B | 0.8724 | 0.0904 | −0.0712 | 0.022* | |
C5B | 0.9025 (2) | 0.2985 (2) | −0.09994 (14) | 0.0173 (4) | |
C6B | 1.0529 (2) | 0.3429 (2) | −0.14259 (14) | 0.0176 (4) | |
C7B | 1.1047 (3) | 0.4777 (2) | −0.17281 (17) | 0.0257 (5) | |
H7B | 1.0442 | 0.5445 | −0.1650 | 0.031* | |
C8B | 1.2461 (3) | 0.5135 (2) | −0.21452 (17) | 0.0267 (5) | |
H8B | 1.2794 | 0.6040 | −0.2344 | 0.032* | |
C9B | 1.3368 (2) | 0.4163 (2) | −0.22663 (16) | 0.0237 (5) | |
H9B | 1.4312 | 0.4405 | −0.2547 | 0.028* | |
C10B | 1.2868 (3) | 0.2819 (3) | −0.19674 (19) | 0.0301 (5) | |
H10B | 1.3475 | 0.2152 | −0.2050 | 0.036* | |
C11B | 1.1465 (3) | 0.2465 (3) | −0.15450 (18) | 0.0275 (5) | |
H11B | 1.1147 | 0.1566 | −0.1338 | 0.033* | |
N2 | 0.63040 (19) | −0.15390 (19) | −0.04664 (13) | 0.0195 (4) | |
C12 | 0.6937 (2) | −0.2233 (2) | −0.09897 (15) | 0.0176 (4) | |
S | 0.78707 (7) | −0.31891 (7) | −0.17439 (4) | 0.02719 (15) | |
C13 | 0.2128 (4) | 0.4090 (3) | 0.4679 (2) | 0.0525 (8) | |
H13A | 0.1614 | 0.4020 | 0.5264 | 0.079* | |
H13B | 0.1868 | 0.4845 | 0.4389 | 0.079* | |
H13C | 0.3295 | 0.4386 | 0.4883 | 0.079* | |
O1 | 0.15494 (19) | 0.2647 (2) | 0.39439 (13) | 0.0382 (4) | |
H1 | 0.199 (3) | 0.274 (4) | 0.3431 (15) | 0.057* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co | 0.01664 (19) | 0.0152 (2) | 0.01317 (19) | 0.00462 (14) | 0.00512 (15) | 0.00379 (14) |
N1A | 0.0180 (8) | 0.0248 (10) | 0.0176 (9) | 0.0057 (7) | 0.0020 (7) | 0.0050 (7) |
C2A | 0.0191 (9) | 0.0197 (11) | 0.0170 (10) | 0.0062 (8) | 0.0049 (8) | 0.0043 (8) |
N3A | 0.0192 (8) | 0.0168 (9) | 0.0164 (8) | 0.0054 (7) | 0.0055 (7) | 0.0043 (7) |
C4A | 0.0201 (9) | 0.0200 (11) | 0.0181 (10) | 0.0062 (8) | 0.0078 (8) | 0.0061 (8) |
C5A | 0.0220 (10) | 0.0181 (10) | 0.0179 (10) | 0.0065 (8) | 0.0058 (8) | 0.0050 (8) |
C6A | 0.0280 (11) | 0.0214 (11) | 0.0170 (10) | 0.0017 (9) | 0.0042 (9) | 0.0040 (8) |
C7A | 0.0285 (11) | 0.0378 (14) | 0.0229 (11) | 0.0014 (10) | 0.0020 (10) | 0.0078 (10) |
C8A | 0.0446 (15) | 0.0470 (16) | 0.0181 (11) | −0.0040 (12) | −0.0054 (11) | 0.0097 (11) |
C9A | 0.0544 (16) | 0.0383 (15) | 0.0168 (11) | −0.0031 (12) | 0.0103 (12) | 0.0022 (10) |
C10A | 0.0447 (14) | 0.0310 (14) | 0.0252 (12) | 0.0057 (11) | 0.0162 (11) | 0.0022 (10) |
C11A | 0.0323 (11) | 0.0256 (12) | 0.0199 (11) | 0.0049 (9) | 0.0061 (9) | 0.0023 (9) |
N1B | 0.0243 (8) | 0.0172 (9) | 0.0227 (9) | 0.0080 (7) | 0.0101 (7) | 0.0079 (7) |
C2B | 0.0216 (10) | 0.0193 (11) | 0.0200 (10) | 0.0056 (8) | 0.0080 (8) | 0.0045 (8) |
N3B | 0.0180 (8) | 0.0167 (9) | 0.0172 (8) | 0.0036 (7) | 0.0038 (7) | 0.0036 (7) |
C4B | 0.0187 (9) | 0.0186 (10) | 0.0195 (10) | 0.0071 (8) | 0.0047 (8) | 0.0055 (8) |
C5B | 0.0186 (9) | 0.0164 (10) | 0.0145 (9) | 0.0054 (8) | 0.0017 (8) | 0.0008 (8) |
C6B | 0.0168 (9) | 0.0187 (10) | 0.0127 (9) | 0.0023 (8) | 0.0003 (8) | 0.0011 (8) |
C7B | 0.0283 (11) | 0.0198 (11) | 0.0336 (12) | 0.0111 (9) | 0.0151 (10) | 0.0076 (9) |
C8B | 0.0300 (11) | 0.0160 (11) | 0.0341 (12) | 0.0044 (9) | 0.0146 (10) | 0.0074 (9) |
C9B | 0.0196 (10) | 0.0245 (12) | 0.0253 (11) | 0.0045 (8) | 0.0100 (9) | 0.0044 (9) |
C10B | 0.0272 (11) | 0.0315 (13) | 0.0421 (14) | 0.0170 (10) | 0.0159 (10) | 0.0161 (11) |
C11B | 0.0266 (11) | 0.0266 (12) | 0.0367 (13) | 0.0114 (9) | 0.0119 (10) | 0.0170 (10) |
N2 | 0.0209 (8) | 0.0192 (9) | 0.0199 (9) | 0.0070 (7) | 0.0060 (7) | 0.0068 (7) |
C12 | 0.0140 (9) | 0.0176 (10) | 0.0207 (10) | 0.0018 (8) | 0.0027 (8) | 0.0091 (8) |
S | 0.0298 (3) | 0.0282 (3) | 0.0332 (3) | 0.0158 (2) | 0.0186 (2) | 0.0128 (2) |
C13 | 0.0496 (16) | 0.0419 (17) | 0.0497 (17) | −0.0032 (13) | 0.0053 (14) | 0.0066 (14) |
O1 | 0.0300 (9) | 0.0495 (11) | 0.0311 (9) | 0.0059 (8) | 0.0042 (7) | 0.0130 (8) |
Geometric parameters (Å, º) top
Co—N3Ai | 2.1194 (16) | N1B—C5B | 1.374 (3) |
Co—N3A | 2.1195 (16) | N1B—H1B | 0.854 (10) |
Co—N2i | 2.1241 (17) | C2B—N3B | 1.318 (3) |
Co—N2 | 2.1241 (17) | C2B—H2B | 0.9300 |
Co—N3B | 2.1452 (16) | N3B—C4B | 1.380 (2) |
Co—N3Bi | 2.1452 (16) | C4B—C5B | 1.362 (3) |
N1A—C2A | 1.344 (3) | C4B—H4B | 0.9300 |
N1A—C5A | 1.376 (3) | C5B—C6B | 1.471 (3) |
N1A—H1A | 0.861 (10) | C6B—C11B | 1.385 (3) |
C2A—N3A | 1.318 (2) | C6B—C7B | 1.390 (3) |
C2A—H2A | 0.9300 | C7B—C8B | 1.389 (3) |
N3A—C4A | 1.377 (2) | C7B—H7B | 0.9300 |
C4A—C5A | 1.358 (3) | C8B—C9B | 1.371 (3) |
C4A—H4A | 0.9300 | C8B—H8B | 0.9300 |
C5A—C6A | 1.469 (3) | C9B—C10B | 1.384 (3) |
C6A—C7A | 1.390 (3) | C9B—H9B | 0.9300 |
C6A—C11A | 1.394 (3) | C10B—C11B | 1.385 (3) |
C7A—C8A | 1.389 (3) | C10B—H10B | 0.9300 |
C7A—H7A | 0.9300 | C11B—H11B | 0.9300 |
C8A—C9A | 1.377 (4) | N2—C12 | 1.152 (3) |
C8A—H8A | 0.9300 | C12—S | 1.650 (2) |
C9A—C10A | 1.375 (4) | C13—O1 | 1.413 (3) |
C9A—H9A | 0.9300 | C13—H13A | 0.9600 |
C10A—C11A | 1.385 (3) | C13—H13B | 0.9600 |
C10A—H10A | 0.9300 | C13—H13C | 0.9600 |
C11A—H11A | 0.9300 | O1—H1 | 0.840 (10) |
N1B—C2B | 1.345 (3) | | |
| | | |
N3Ai—Co—N3A | 180.0 | C10A—C11A—C6A | 120.3 (2) |
N3Ai—Co—N2i | 91.85 (6) | C10A—C11A—H11A | 119.9 |
N3A—Co—N2i | 88.15 (6) | C6A—C11A—H11A | 119.9 |
N3Ai—Co—N2 | 88.15 (6) | C2B—N1B—C5B | 108.22 (18) |
N3A—Co—N2 | 91.85 (6) | C2B—N1B—H1B | 124.0 (16) |
N2i—Co—N2 | 180.0 | C5B—N1B—H1B | 127.7 (16) |
N3Ai—Co—N3B | 88.63 (6) | N3B—C2B—N1B | 111.28 (18) |
N3A—Co—N3B | 91.37 (6) | N3B—C2B—H2B | 124.4 |
N2i—Co—N3B | 91.49 (6) | N1B—C2B—H2B | 124.4 |
N2—Co—N3B | 88.51 (6) | C2B—N3B—C4B | 105.14 (17) |
N3Ai—Co—N3Bi | 91.37 (6) | C2B—N3B—Co | 125.05 (13) |
N3A—Co—N3Bi | 88.63 (6) | C4B—N3B—Co | 129.30 (14) |
N2i—Co—N3Bi | 88.51 (6) | C5B—C4B—N3B | 110.55 (18) |
N2—Co—N3Bi | 91.49 (6) | C5B—C4B—H4B | 124.7 |
N3B—Co—N3Bi | 180.0 | N3B—C4B—H4B | 124.7 |
C2A—N1A—C5A | 107.82 (16) | C4B—C5B—N1B | 104.81 (17) |
C2A—N1A—H1A | 126.3 (16) | C4B—C5B—C6B | 130.81 (19) |
C5A—N1A—H1A | 125.9 (16) | N1B—C5B—C6B | 124.34 (18) |
N3A—C2A—N1A | 111.18 (18) | C11B—C6B—C7B | 118.20 (19) |
N3A—C2A—H2A | 124.4 | C11B—C6B—C5B | 119.11 (19) |
N1A—C2A—H2A | 124.4 | C7B—C6B—C5B | 122.69 (19) |
C2A—N3A—C4A | 105.52 (16) | C6B—C7B—C8B | 120.6 (2) |
C2A—N3A—Co | 127.11 (13) | C6B—C7B—H7B | 119.7 |
C4A—N3A—Co | 127.33 (13) | C8B—C7B—H7B | 119.7 |
C5A—C4A—N3A | 110.20 (17) | C9B—C8B—C7B | 120.5 (2) |
C5A—C4A—H4A | 124.9 | C9B—C8B—H8B | 119.7 |
N3A—C4A—H4A | 124.9 | C7B—C8B—H8B | 119.7 |
C4A—C5A—N1A | 105.28 (17) | C8B—C9B—C10B | 119.50 (19) |
C4A—C5A—C6A | 131.59 (18) | C8B—C9B—H9B | 120.3 |
N1A—C5A—C6A | 123.13 (18) | C10B—C9B—H9B | 120.3 |
C7A—C6A—C11A | 119.0 (2) | C9B—C10B—C11B | 120.1 (2) |
C7A—C6A—C5A | 121.4 (2) | C9B—C10B—H10B | 120.0 |
C11A—C6A—C5A | 119.5 (2) | C11B—C10B—H10B | 120.0 |
C8A—C7A—C6A | 120.0 (2) | C6B—C11B—C10B | 121.1 (2) |
C8A—C7A—H7A | 120.0 | C6B—C11B—H11B | 119.5 |
C6A—C7A—H7A | 120.0 | C10B—C11B—H11B | 119.5 |
C9A—C8A—C7A | 120.4 (2) | C12—N2—Co | 158.73 (17) |
C9A—C8A—H8A | 119.8 | N2—C12—S | 178.69 (19) |
C7A—C8A—H8A | 119.8 | O1—C13—H13A | 109.5 |
C10A—C9A—C8A | 120.0 (2) | O1—C13—H13B | 109.5 |
C10A—C9A—H9A | 120.0 | H13A—C13—H13B | 109.5 |
C8A—C9A—H9A | 120.0 | O1—C13—H13C | 109.5 |
C9A—C10A—C11A | 120.2 (2) | H13A—C13—H13C | 109.5 |
C9A—C10A—H10A | 119.9 | H13B—C13—H13C | 109.5 |
C11A—C10A—H10A | 119.9 | C13—O1—H1 | 108 (2) |
Symmetry code: (i) −x+1, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O1ii | 0.86 (2) | 2.00 (2) | 2.853 (3) | 174 (2) |
N1B—H1B···Siii | 0.85 (2) | 2.49 (2) | 3.328 (2) | 167 (2) |
O1—H1···Si | 0.84 (2) | 2.44 (2) | 3.224 (2) | 155 (2) |
Symmetry codes: (i) −x+1, −y, −z; (ii) x+1, y, z; (iii) x, y+1, z. |
Crystal data top
C20H16CoN6S2 | F(000) = 948 |
Mr = 463.44 | Dx = 1.517 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 24.4747 (19) Å | Cell parameters from 1570 reflections |
b = 5.5932 (5) Å | θ = 4.6–29.3° |
c = 14.8644 (16) Å | µ = 1.07 mm−1 |
β = 94.172 (8)° | T = 100 K |
V = 2029.4 (3) Å3 | Prism, blue |
Z = 4 | 0.15 × 0.09 × 0.09 mm |
Data collection top
Oxford Diffraction SuperNova with Atlas CCD detector diffractometer | 2176 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 1794 reflections with I > 2σ(I) |
Detector resolution: 10.4223 pixels mm-1 | Rint = 0.030 |
ω scans | θmax = 27.0°, θmin = 3.3° |
Absorption correction: multi-scan CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | h = −30→24 |
Tmin = 0.935, Tmax = 1.000 | k = −5→7 |
4333 measured reflections | l = −18→17 |
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)] = 0.033 | Hydrogen site location: mixed |
wR(F2) = 0.077 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0224P)2 + 3.0766P] where P = (Fo2 + 2Fc2)/3 |
2176 reflections | (Δ/σ)max = 0.001 |
135 parameters | Δρmax = 0.43 e Å−3 |
1 restraint | Δρmin = −0.27 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Co | 0.5000 | 0.71417 (8) | 0.7500 | 0.01835 (13) | |
N1 | 0.39936 (7) | 0.2486 (3) | 0.59807 (12) | 0.0183 (4) | |
H1 | 0.3954 (10) | 0.129 (3) | 0.5626 (14) | 0.027* | |
C2 | 0.44728 (8) | 0.3524 (4) | 0.62177 (14) | 0.0208 (5) | |
H2 | 0.4801 | 0.3141 | 0.5974 | 0.025* | |
N3 | 0.44203 (7) | 0.5165 (3) | 0.68420 (11) | 0.0183 (4) | |
C4 | 0.38688 (8) | 0.5172 (4) | 0.70008 (14) | 0.0182 (5) | |
H4 | 0.3709 | 0.6166 | 0.7409 | 0.022* | |
C5 | 0.35966 (8) | 0.3511 (4) | 0.64724 (13) | 0.0157 (4) | |
C6 | 0.30160 (8) | 0.2847 (4) | 0.63634 (13) | 0.0150 (4) | |
C7 | 0.28427 (8) | 0.0706 (4) | 0.59538 (13) | 0.0173 (4) | |
H7 | 0.3099 | −0.0377 | 0.5766 | 0.021* | |
C8 | 0.22878 (8) | 0.0193 (4) | 0.58257 (13) | 0.0182 (4) | |
H8 | 0.2175 | −0.1234 | 0.5551 | 0.022* | |
C9 | 0.19019 (8) | 0.1782 (4) | 0.61027 (13) | 0.0173 (4) | |
H9 | 0.1531 | 0.1438 | 0.6004 | 0.021* | |
C10 | 0.20690 (8) | 0.3885 (4) | 0.65270 (13) | 0.0163 (4) | |
H10 | 0.1810 | 0.4944 | 0.6724 | 0.020* | |
C11 | 0.26228 (8) | 0.4416 (4) | 0.66587 (13) | 0.0148 (4) | |
H11 | 0.2733 | 0.5831 | 0.6946 | 0.018* | |
N2 | 0.45765 (7) | 0.9051 (4) | 0.83063 (13) | 0.0243 (4) | |
C12 | 0.43880 (8) | 1.0272 (4) | 0.88384 (15) | 0.0185 (5) | |
S | 0.41467 (2) | 1.20455 (10) | 0.95819 (4) | 0.02081 (15) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co | 0.0102 (2) | 0.0229 (2) | 0.0220 (2) | 0.000 | 0.00118 (15) | 0.000 |
N1 | 0.0168 (8) | 0.0183 (10) | 0.0201 (10) | 0.0038 (8) | 0.0032 (7) | −0.0032 (7) |
C2 | 0.0146 (10) | 0.0251 (12) | 0.0230 (11) | 0.0059 (9) | 0.0036 (8) | 0.0024 (10) |
N3 | 0.0127 (8) | 0.0214 (10) | 0.0207 (9) | 0.0006 (8) | 0.0020 (7) | 0.0004 (8) |
C4 | 0.0127 (9) | 0.0234 (12) | 0.0187 (10) | 0.0004 (9) | 0.0027 (8) | −0.0017 (9) |
C5 | 0.0146 (9) | 0.0177 (11) | 0.0149 (10) | 0.0043 (9) | 0.0020 (8) | 0.0033 (8) |
C6 | 0.0157 (10) | 0.0180 (11) | 0.0112 (10) | −0.0001 (9) | −0.0001 (7) | 0.0025 (8) |
C7 | 0.0208 (10) | 0.0153 (11) | 0.0160 (10) | 0.0027 (9) | 0.0020 (8) | 0.0006 (9) |
C8 | 0.0239 (11) | 0.0152 (11) | 0.0150 (10) | −0.0029 (9) | −0.0018 (8) | 0.0024 (9) |
C9 | 0.0157 (9) | 0.0237 (11) | 0.0121 (10) | −0.0038 (9) | −0.0012 (8) | 0.0023 (9) |
C10 | 0.0161 (10) | 0.0200 (11) | 0.0129 (10) | 0.0020 (9) | 0.0014 (8) | 0.0014 (8) |
C11 | 0.0162 (9) | 0.0147 (10) | 0.0131 (10) | −0.0009 (8) | −0.0005 (7) | −0.0005 (8) |
N2 | 0.0164 (9) | 0.0268 (11) | 0.0296 (11) | −0.0013 (8) | 0.0012 (8) | −0.0043 (9) |
C12 | 0.0112 (9) | 0.0191 (11) | 0.0246 (11) | −0.0029 (9) | −0.0028 (8) | 0.0036 (9) |
S | 0.0190 (3) | 0.0190 (3) | 0.0249 (3) | −0.0007 (2) | 0.0054 (2) | −0.0006 (2) |
Geometric parameters (Å, º) top
Co—N2 | 1.9576 (19) | C6—C11 | 1.397 (3) |
Co—N2i | 1.9576 (19) | C6—C7 | 1.395 (3) |
Co—N3i | 1.9974 (18) | C7—C8 | 1.388 (3) |
Co—N3 | 1.9974 (18) | C7—H7 | 0.9300 |
N1—C2 | 1.333 (3) | C8—C9 | 1.381 (3) |
N1—C5 | 1.382 (3) | C8—H8 | 0.9300 |
N1—H1 | 0.852 (10) | C9—C10 | 1.383 (3) |
C2—N3 | 1.318 (3) | C9—H9 | 0.9300 |
C2—H2 | 0.9300 | C10—C11 | 1.388 (3) |
N3—C4 | 1.387 (2) | C10—H10 | 0.9300 |
C4—C5 | 1.359 (3) | C11—H11 | 0.9300 |
C4—H4 | 0.9300 | N2—C12 | 1.165 (3) |
C5—C6 | 1.466 (3) | C12—S | 1.628 (2) |
| | | |
N2—Co—N2i | 113.88 (12) | C11—C6—C7 | 118.83 (19) |
N2—Co—N3i | 113.01 (7) | C11—C6—C5 | 119.36 (19) |
N2i—Co—N3i | 102.29 (7) | C7—C6—C5 | 121.80 (19) |
N2—Co—N3 | 102.29 (7) | C8—C7—C6 | 120.05 (19) |
N2i—Co—N3 | 113.02 (7) | C8—C7—H7 | 120.0 |
N3i—Co—N3 | 112.80 (10) | C6—C7—H7 | 120.0 |
C2—N1—C5 | 108.56 (18) | C9—C8—C7 | 120.6 (2) |
C2—N1—H1 | 124.4 (16) | C9—C8—H8 | 119.7 |
C5—N1—H1 | 126.8 (16) | C7—C8—H8 | 119.7 |
N3—C2—N1 | 111.13 (18) | C8—C9—C10 | 119.83 (19) |
N3—C2—H2 | 124.4 | C8—C9—H9 | 120.1 |
N1—C2—H2 | 124.4 | C10—C9—H9 | 120.1 |
C2—N3—C4 | 105.52 (18) | C9—C10—C11 | 120.00 (19) |
C2—N3—Co | 128.89 (14) | C9—C10—H10 | 120.0 |
C4—N3—Co | 125.49 (14) | C11—C10—H10 | 120.0 |
C5—C4—N3 | 109.99 (18) | C10—C11—C6 | 120.62 (19) |
C5—C4—H4 | 125.0 | C10—C11—H11 | 119.7 |
N3—C4—H4 | 125.0 | C6—C11—H11 | 119.7 |
C4—C5—N1 | 104.79 (17) | C12—N2—Co | 171.38 (17) |
C4—C5—C6 | 131.85 (19) | N2—C12—S | 177.68 (19) |
N1—C5—C6 | 123.34 (19) | | |
Symmetry code: (i) −x+1, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Sii | 0.85 (2) | 2.49 (2) | 3.317 (2) | 162 (2) |
Symmetry code: (ii) x, −y+1, z−1/2. |
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