metal-organic compounds
Bis[N5,N7-bis(pyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine-5,7-diimine]cobalt(III) perchlorate acetonitrile disolvate
aInstitute of Chemistry, University of Neuchâtel, Av de Bellevaux 51, CH-2000 Neuchâtel, Switzerland, and bInstitute of Physics, University of Neuchâtel, rue Emile-Argand 11, CH-2000 Neuchâtel, Switzerland
*Correspondence e-mail: helen.stoeckli-evans@unine.ch
In the title complex, [Co(C16H10N7)2]ClO4·2CH3CN, the cation possesses twofold rotational symmetry. The CoIII ion is located on a twofold rotation axis and is octahedrally coordinated to two tridentate `pincer' ligands. The Cl atom of the perchlorate anion is located on a fourfold rotoinversion axis. In the crystal, the cations are linked via C—H⋯O and C—H⋯N hydrogen bonds involving the perchlorate anion and the solvate acetonitrile molecules. These interactions lead to the formation of a supramolecular three-dimensional framework.
Keywords: crystal structure; pyrrolopyrazine; pincer ligand; isoindoline analogue; cobalt(III); hydrogen bonding; supramolecular framework.
CCDC reference: 1844111
Structure description
Symmetrically substituted isoindolines, such as 1,3-bis(2-pyridylinimo)isoindoline (Schilf, 2004), are ideal tridentate `pincer' ligands. For example, two isotypic cobalt(II) complexes of deprotonated 1,3-bis(2-pyridylinimo)isoindoline have been synthesized and their interaction with calf-thymus DNA studied (Selvi et al., 2005). The same ligand has been used to form a neutral square-planar platinum(II) complex that has a bright-orange to red room temperature luminescence in fluid dichloromethane solutions (Wen et al., 2010).
The pyrazine analogue of 1,3-bis(2-pyridylinimo)isoindoline, viz. (5Z,7Z)-N5,N7-di(pyridin-2-yl)-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-diimine (L) (Posel & Stoeckli-Evans, 2018), was synthesized in order to study its coordination behaviour with transition metals (Posel, 1998). Herein, we describe one such complex synthesized by the reaction of L with cobalt perchlorate.
The molecular structure of the title complex cation is illustrated in Fig. 1. It possesses twofold rotational symmetry with the cobalt atom located on a twofold rotation axis. It is ligated by six N atoms from two deprotonated tridentate L ligands, hence it has an almost perfect octahedral coordination sphere. The Co—Nimine bond length (Co1—N5) is 1.885 (5) Å, shorter than the Co—Npyridine bond lengths (Co1—N4 and Co1—N7) of 1.983 (6) and 1.979 (5) Å. These bond lengths are very similar to those observed in the two isotypic bis(1,3-bis(2-pyridylimino)isoindoline)cobalt(III) perchlorate methanol solvate complexes mentioned above (space groups C2 and P21/c), where the Co—Nimine bond lengths vary from ca 1.885 to 1.890 Å, and the Co—Npyridine bond lengths vary from ca 1.971 to 1.986 Å.
On coordination, the ligand molecules are extremely twisted compared to the situation in the free ligand, which is relatively planar with an r.m.s. deviation of 0.061 Å for all 23 non-H atoms (Posel & Stoeckli-Evans, 2018). In the complex cation, the pyridine rings (N4/C6–C10) and (N7/C12–C16) are inclined to the mean plane of the pyrrolopyrazine unit (N1/N2/N5/C1–C5/C11) by 28.3 (3) and 30.9 (3)°, respectively, and by 53.6 (3)° to each other. This arrangement is similar to that observed for the isotypic bis(1,3-bis(2-pyridylimino)isoindoline)cobalt(III) perchlorate methanol solvate complexes mentioned above.
In the crystal, the cations are linked via C—H⋯Operchlorate and C—H⋯Nacetonitrile hydrogen bonds, forming a supramolecular three-dimensional framework (Table 1 and Fig. 2).
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There are small cavities in the ca 72 Å3 (ca 1% of the unit-cell volume). They are represented in brown–yellow in Fig. 3. There is no evidence of any residual electron density being present in these cavities on examination of the final difference-Fourier map (see Table 2).
with a total potential solvent area volume ofSynthesis and crystallization
The title compound was synthesized by the reaction of (5Z,7Z)-N5,N7-di(pyridin-2-yl)-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-diimine (L) (Posel & Stoeckli-Evans, 2018) with Co(ClO4)2.
In a round-bottomed flask were mixed 0.0646 g (0.00021 mol) of ligand L in 7 ml of dry methanol and 0.1 ml of triethylamine. Then a solution of 0.0366 g (0.0001 mol) of Co(ClO4)2·6H2O in 3 ml of dry methanol was added. The mixture was stirred at room temperature for 48 h. The main product, a brown–black powder, was filtered off and dried in a vacuum desiccator over silica (yield ∼0.03 g, 36%; m.p. >623 K). This solid was then used for recrystallization from a mixture of acetonitrile/methanol (1/1, v/v), which gave a small amount of brown–black block-like crystals. Analysis for [(C16H10N7)2Co]·ClO4·2(CH3CN) (840.0931 g mol−1): calculated C 51.47, H 3.12, N 26.65%; found C 50.68, H 3.11, N 26.18%. IR (KBr pellet. cm−1): 2244, 1611, 1579, 1537, 1450, 1359, 1221, 1144, 1089, 782, 748, 650, 548, 437.
Refinement
Crystal data, data collection and structure . The Cl atom of the perchlorate anion is located on a fourfold rotoinversion axis, and two O atoms (O2 and O3) are partially disordered (occupancies of 0.5 each). The intensity data were measured at room temperature using a four-circle diffractometer. No absorption correction was applied as there were no suitable reflections for ψ scans.
details are summarized in Table 2Structural data
CCDC reference: 1844111
https://doi.org/10.1107/S241431461800754X/bh4036sup1.cif
contains datablocks I, Global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461800754X/bh4036Isup2.hkl
Data collection: STADI4 (Stoe & Cie, 1997); cell
STADI4 (Stoe & Cie, 1997); data reduction: X-RED (Stoe & Cie, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).[Co(C16H10N7)2]ClO4·2C2H3N | Dx = 1.527 Mg m−3 |
Mr = 841.11 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, I42d | Cell parameters from 18 reflections |
a = 19.9756 (17) Å | θ = 14.0–17.5° |
c = 18.3409 (18) Å | µ = 0.61 mm−1 |
V = 7318.5 (14) Å3 | T = 293 K |
Z = 8 | Block, brown–black |
F(000) = 3440 | 0.61 × 0.57 × 0.51 mm |
Stoe–Siemens AED2 4-circle diffractometer | Rint = 0.046 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.0° |
Plane graphite monochromator | h = −16→16 |
ω/2θ scans | k = 0→23 |
3245 measured reflections | l = 0→21 |
3148 independent reflections | 2 standard reflections every 60 min |
2352 reflections with I > 2σ(I) | intensity decay: 2% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0532P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max = 0.001 |
3148 reflections | Δρmax = 0.28 e Å−3 |
273 parameters | Δρmin = −0.30 e Å−3 |
0 restraints | Absolute structure: Flack x determined using 815 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.05 (3) |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Co1 | 0.250000 | 0.32578 (6) | 0.375000 | 0.0317 (3) | |
N1 | 0.4124 (3) | 0.3449 (3) | 0.1426 (3) | 0.0523 (16) | |
N2 | 0.4962 (3) | 0.2988 (3) | 0.2590 (3) | 0.0496 (16) | |
N3 | 0.4069 (3) | 0.2768 (3) | 0.3910 (3) | 0.0383 (13) | |
N4 | 0.2948 (3) | 0.2569 (3) | 0.4357 (3) | 0.0356 (12) | |
N5 | 0.3249 (3) | 0.3256 (3) | 0.3125 (2) | 0.0333 (12) | |
N6 | 0.2759 (3) | 0.3747 (3) | 0.2050 (3) | 0.0410 (14) | |
N7 | 0.2088 (3) | 0.3960 (3) | 0.3135 (3) | 0.0355 (13) | |
C1 | 0.4774 (4) | 0.3335 (4) | 0.1360 (4) | 0.059 (2) | |
H1 | 0.496793 | 0.340028 | 0.090421 | 0.071* | |
C2 | 0.5184 (4) | 0.3124 (4) | 0.1922 (4) | 0.056 (2) | |
H2 | 0.563872 | 0.307431 | 0.182886 | 0.067* | |
C3 | 0.4310 (3) | 0.3115 (3) | 0.2660 (4) | 0.0373 (16) | |
C4 | 0.3912 (3) | 0.3331 (3) | 0.2099 (3) | 0.0375 (16) | |
C5 | 0.3881 (3) | 0.3036 (3) | 0.3308 (3) | 0.0338 (16) | |
C6 | 0.3625 (3) | 0.2532 (4) | 0.4425 (3) | 0.0388 (15) | |
C7 | 0.3912 (4) | 0.2167 (4) | 0.5000 (4) | 0.061 (2) | |
H7 | 0.437456 | 0.216834 | 0.505894 | 0.074* | |
C8 | 0.3531 (4) | 0.1815 (5) | 0.5469 (4) | 0.068 (3) | |
H8 | 0.372497 | 0.158673 | 0.585743 | 0.082* | |
C9 | 0.2845 (4) | 0.1798 (4) | 0.5360 (4) | 0.059 (2) | |
H9 | 0.257089 | 0.154050 | 0.565874 | 0.071* | |
C10 | 0.2578 (4) | 0.2170 (3) | 0.4802 (4) | 0.0450 (17) | |
H10 | 0.211885 | 0.214784 | 0.472461 | 0.054* | |
C11 | 0.3235 (4) | 0.3455 (3) | 0.2405 (3) | 0.0355 (15) | |
C12 | 0.2207 (3) | 0.4021 (3) | 0.2399 (4) | 0.0361 (16) | |
C13 | 0.1813 (4) | 0.4438 (3) | 0.1971 (4) | 0.0410 (17) | |
H13 | 0.187905 | 0.445373 | 0.146947 | 0.049* | |
C14 | 0.1324 (4) | 0.4828 (4) | 0.2286 (4) | 0.0503 (19) | |
H14 | 0.104580 | 0.509249 | 0.199938 | 0.060* | |
C15 | 0.1255 (4) | 0.4820 (4) | 0.3025 (4) | 0.0489 (19) | |
H15 | 0.096083 | 0.511310 | 0.325368 | 0.059* | |
C16 | 0.1623 (3) | 0.4377 (3) | 0.3429 (4) | 0.0406 (17) | |
H16 | 0.155166 | 0.436012 | 0.392920 | 0.049* | |
N8 | 0.1199 (5) | 0.1258 (4) | 0.4430 (5) | 0.097 (3) | |
C17 | 0.0661 (6) | 0.1296 (5) | 0.4271 (5) | 0.072 (3) | |
C18 | −0.0026 (5) | 0.1357 (6) | 0.4052 (6) | 0.092 (3) | |
H18A | −0.013282 | 0.182072 | 0.398060 | 0.138* | |
H18B | −0.030970 | 0.117374 | 0.442438 | 0.138* | |
H18C | −0.009440 | 0.111691 | 0.360476 | 0.138* | |
Cl1 | 0.000000 | 0.000000 | 0.21977 (17) | 0.0721 (9) | |
O1 | 0.0549 (4) | 0.0048 (9) | 0.1770 (6) | 0.185 (5) | |
O2 | −0.0216 (13) | 0.011 (2) | 0.2881 (8) | 0.175 (12) | 0.5 |
O3 | −0.0089 (16) | 0.0710 (8) | 0.2249 (8) | 0.179 (11) | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0355 (7) | 0.0326 (7) | 0.0270 (6) | 0.000 | −0.0011 (6) | 0.000 |
N1 | 0.061 (4) | 0.058 (4) | 0.038 (4) | 0.008 (3) | 0.012 (3) | 0.003 (3) |
N2 | 0.040 (3) | 0.056 (4) | 0.053 (4) | 0.004 (3) | 0.003 (3) | 0.000 (3) |
N3 | 0.037 (3) | 0.041 (3) | 0.037 (3) | −0.001 (2) | −0.007 (3) | 0.007 (3) |
N4 | 0.041 (3) | 0.035 (3) | 0.031 (3) | −0.002 (3) | 0.002 (2) | 0.002 (3) |
N5 | 0.036 (3) | 0.037 (3) | 0.027 (3) | 0.004 (3) | −0.002 (3) | 0.000 (2) |
N6 | 0.047 (3) | 0.044 (3) | 0.032 (3) | 0.010 (3) | −0.003 (3) | 0.002 (3) |
N7 | 0.038 (3) | 0.033 (3) | 0.035 (3) | 0.001 (3) | 0.001 (3) | 0.002 (3) |
C1 | 0.060 (5) | 0.073 (5) | 0.044 (5) | 0.008 (4) | 0.025 (4) | 0.000 (4) |
C2 | 0.045 (5) | 0.069 (6) | 0.054 (5) | 0.002 (4) | 0.016 (4) | 0.005 (4) |
C3 | 0.040 (4) | 0.032 (4) | 0.041 (4) | −0.003 (3) | 0.003 (3) | −0.002 (3) |
C4 | 0.051 (4) | 0.033 (4) | 0.029 (4) | 0.004 (3) | 0.005 (3) | −0.003 (3) |
C5 | 0.035 (4) | 0.031 (4) | 0.035 (4) | 0.001 (3) | −0.003 (3) | −0.003 (3) |
C6 | 0.043 (4) | 0.036 (4) | 0.037 (4) | 0.000 (4) | −0.003 (3) | 0.004 (3) |
C7 | 0.055 (5) | 0.073 (5) | 0.056 (5) | −0.004 (4) | −0.010 (4) | 0.022 (5) |
C8 | 0.067 (6) | 0.089 (7) | 0.049 (5) | 0.009 (5) | −0.004 (4) | 0.039 (5) |
C9 | 0.073 (6) | 0.049 (5) | 0.054 (5) | 0.006 (4) | 0.014 (4) | 0.023 (4) |
C10 | 0.056 (5) | 0.033 (3) | 0.045 (4) | 0.000 (4) | 0.008 (4) | 0.008 (3) |
C11 | 0.044 (4) | 0.036 (4) | 0.026 (3) | 0.003 (3) | 0.000 (3) | −0.004 (3) |
C12 | 0.038 (4) | 0.035 (4) | 0.035 (4) | −0.003 (3) | −0.004 (3) | 0.001 (3) |
C13 | 0.047 (4) | 0.040 (4) | 0.036 (4) | −0.002 (3) | −0.004 (3) | 0.011 (3) |
C14 | 0.040 (4) | 0.050 (5) | 0.061 (5) | 0.005 (4) | −0.013 (4) | 0.019 (4) |
C15 | 0.047 (5) | 0.036 (4) | 0.063 (5) | 0.008 (3) | 0.004 (4) | 0.008 (4) |
C16 | 0.037 (4) | 0.040 (4) | 0.045 (4) | 0.005 (3) | 0.003 (3) | 0.000 (3) |
N8 | 0.091 (6) | 0.081 (6) | 0.118 (8) | −0.002 (6) | −0.028 (6) | −0.002 (6) |
C17 | 0.087 (8) | 0.063 (6) | 0.067 (6) | −0.002 (6) | −0.009 (6) | −0.015 (5) |
C18 | 0.070 (7) | 0.111 (8) | 0.096 (8) | −0.010 (6) | −0.009 (6) | −0.027 (7) |
Cl1 | 0.059 (2) | 0.108 (3) | 0.0493 (18) | 0.010 (2) | 0.000 | 0.000 |
O1 | 0.067 (5) | 0.343 (17) | 0.146 (8) | −0.008 (8) | 0.010 (6) | 0.002 (10) |
O2 | 0.19 (3) | 0.26 (3) | 0.075 (10) | 0.08 (2) | 0.008 (12) | −0.076 (19) |
O3 | 0.40 (4) | 0.071 (11) | 0.066 (10) | 0.060 (16) | 0.005 (17) | 0.004 (9) |
Co1—N5i | 1.885 (5) | C7—H7 | 0.9300 |
Co1—N5 | 1.885 (5) | C8—C9 | 1.386 (11) |
Co1—N7 | 1.979 (5) | C8—H8 | 0.9300 |
Co1—N7i | 1.979 (5) | C9—C10 | 1.372 (10) |
Co1—N4 | 1.983 (6) | C9—H9 | 0.9300 |
Co1—N4i | 1.983 (6) | C10—H10 | 0.9300 |
N1—C1 | 1.325 (9) | C12—C13 | 1.389 (9) |
N1—C4 | 1.326 (8) | C13—C14 | 1.375 (10) |
N2—C2 | 1.331 (9) | C13—H13 | 0.9300 |
N2—C3 | 1.332 (8) | C14—C15 | 1.363 (11) |
N3—C5 | 1.284 (8) | C14—H14 | 0.9300 |
N3—C6 | 1.378 (8) | C15—C16 | 1.368 (9) |
N4—C10 | 1.359 (8) | C15—H15 | 0.9300 |
N4—C6 | 1.361 (8) | C16—H16 | 0.9300 |
N5—C5 | 1.378 (8) | N8—C17 | 1.116 (11) |
N5—C11 | 1.381 (7) | C17—C18 | 1.436 (14) |
N6—C11 | 1.291 (8) | C18—H18A | 0.9600 |
N6—C12 | 1.387 (8) | C18—H18B | 0.9600 |
N7—C16 | 1.357 (8) | C18—H18C | 0.9600 |
N7—C12 | 1.377 (8) | Cl1—O2ii | 1.343 (15) |
C1—C2 | 1.383 (11) | Cl1—O2 | 1.343 (15) |
C1—H1 | 0.9300 | Cl1—O1 | 1.352 (9) |
C2—H2 | 0.9300 | Cl1—O1ii | 1.352 (9) |
C3—C4 | 1.371 (9) | Cl1—O3 | 1.433 (16) |
C3—C5 | 1.473 (9) | Cl1—O3ii | 1.433 (16) |
C4—C11 | 1.485 (9) | O2—O2ii | 0.96 (4) |
C6—C7 | 1.406 (10) | O2—O3 | 1.69 (4) |
C7—C8 | 1.346 (11) | ||
N5i—Co1—N5 | 179.7 (3) | C9—C8—H8 | 120.7 |
N5i—Co1—N7 | 91.0 (2) | C10—C9—C8 | 118.6 (8) |
N5—Co1—N7 | 89.2 (2) | C10—C9—H9 | 120.7 |
N5i—Co1—N7i | 89.2 (2) | C8—C9—H9 | 120.7 |
N5—Co1—N7i | 91.0 (2) | N4—C10—C9 | 123.7 (7) |
N7—Co1—N7i | 89.7 (3) | N4—C10—H10 | 118.1 |
N5i—Co1—N4 | 90.9 (2) | C9—C10—H10 | 118.1 |
N5—Co1—N4 | 88.9 (2) | N6—C11—N5 | 128.9 (6) |
N7—Co1—N4 | 177.8 (2) | N6—C11—C4 | 123.8 (6) |
N7i—Co1—N4 | 89.1 (2) | N5—C11—C4 | 107.1 (6) |
N5i—Co1—N4i | 88.9 (2) | N7—C12—N6 | 123.7 (6) |
N5—Co1—N4i | 90.9 (2) | N7—C12—C13 | 120.6 (6) |
N7—Co1—N4i | 89.1 (2) | N6—C12—C13 | 115.3 (6) |
N7i—Co1—N4i | 177.8 (2) | C14—C13—C12 | 120.3 (7) |
N4—Co1—N4i | 92.1 (3) | C14—C13—H13 | 119.8 |
C1—N1—C4 | 111.6 (7) | C12—C13—H13 | 119.8 |
C2—N2—C3 | 112.0 (6) | C15—C14—C13 | 118.9 (7) |
C5—N3—C6 | 122.9 (6) | C15—C14—H14 | 120.6 |
C10—N4—C6 | 116.9 (6) | C13—C14—H14 | 120.6 |
C10—N4—Co1 | 120.0 (5) | C14—C15—C16 | 119.4 (7) |
C6—N4—Co1 | 122.5 (5) | C14—C15—H15 | 120.3 |
C5—N5—C11 | 110.1 (5) | C16—C15—H15 | 120.3 |
C5—N5—Co1 | 125.5 (4) | N7—C16—C15 | 123.4 (7) |
C11—N5—Co1 | 124.4 (4) | N7—C16—H16 | 118.3 |
C11—N6—C12 | 122.1 (5) | C15—C16—H16 | 118.3 |
C16—N7—C12 | 116.9 (6) | N8—C17—C18 | 178.5 (14) |
C16—N7—Co1 | 119.6 (4) | C17—C18—H18A | 109.5 |
C12—N7—Co1 | 123.3 (5) | C17—C18—H18B | 109.5 |
N1—C1—C2 | 124.4 (7) | H18A—C18—H18B | 109.5 |
N1—C1—H1 | 117.8 | C17—C18—H18C | 109.5 |
C2—C1—H1 | 117.8 | H18A—C18—H18C | 109.5 |
N2—C2—C1 | 123.5 (7) | H18B—C18—H18C | 109.5 |
N2—C2—H2 | 118.2 | O2ii—Cl1—O2 | 42.0 (16) |
C1—C2—H2 | 118.2 | O2ii—Cl1—O1 | 107.0 (12) |
N2—C3—C4 | 123.7 (6) | O2—Cl1—O1 | 142.4 (15) |
N2—C3—C5 | 128.7 (6) | O2ii—Cl1—O1ii | 142.4 (15) |
C4—C3—C5 | 107.5 (6) | O2—Cl1—O1ii | 107.0 (12) |
N1—C4—C3 | 124.7 (6) | O1—Cl1—O1ii | 109.0 (9) |
N1—C4—C11 | 127.8 (6) | O2ii—Cl1—O3 | 97.7 (19) |
C3—C4—C11 | 107.3 (5) | O2—Cl1—O3 | 75.1 (18) |
N3—C5—N5 | 127.5 (6) | O1—Cl1—O3 | 94.0 (14) |
N3—C5—C3 | 124.7 (6) | O1ii—Cl1—O3 | 90.4 (13) |
N5—C5—C3 | 107.7 (5) | O2ii—Cl1—O3ii | 75.1 (18) |
N4—C6—N3 | 124.0 (6) | O2—Cl1—O3ii | 97.7 (19) |
N4—C6—C7 | 120.1 (6) | O1—Cl1—O3ii | 90.4 (13) |
N3—C6—C7 | 115.4 (6) | O1ii—Cl1—O3ii | 94.0 (14) |
C8—C7—C6 | 121.4 (8) | O3—Cl1—O3ii | 172.5 (13) |
C8—C7—H7 | 119.3 | O2ii—O2—Cl1 | 69.0 (8) |
C6—C7—H7 | 119.3 | O2ii—O2—O3 | 100 (4) |
C7—C8—C9 | 118.7 (8) | Cl1—O2—O3 | 54.9 (13) |
C7—C8—H8 | 120.7 | Cl1—O3—O2 | 50.0 (10) |
N7—Co1—N5—C5 | 157.8 (5) | C6—N4—C10—C9 | 7.6 (10) |
N7i—Co1—N5—C5 | 68.1 (5) | Co1—N4—C10—C9 | −163.8 (5) |
N4—Co1—N5—C5 | −21.0 (5) | C8—C9—C10—N4 | −1.6 (12) |
N4i—Co1—N5—C5 | −113.1 (5) | C12—N6—C11—N5 | 12.3 (10) |
N7—Co1—N5—C11 | −24.6 (5) | C12—N6—C11—C4 | −161.7 (6) |
N7i—Co1—N5—C11 | −114.3 (5) | C5—N5—C11—N6 | −172.9 (6) |
N4—Co1—N5—C11 | 156.6 (5) | Co1—N5—C11—N6 | 9.2 (9) |
N4i—Co1—N5—C11 | 64.5 (5) | C5—N5—C11—C4 | 1.9 (7) |
C4—N1—C1—C2 | −0.6 (11) | Co1—N5—C11—C4 | −176.0 (4) |
C3—N2—C2—C1 | −3.5 (11) | N1—C4—C11—N6 | −4.7 (11) |
N1—C1—C2—N2 | 2.7 (13) | C3—C4—C11—N6 | 170.5 (6) |
C2—N2—C3—C4 | 2.8 (10) | N1—C4—C11—N5 | −179.9 (6) |
C2—N2—C3—C5 | −179.5 (7) | C3—C4—C11—N5 | −4.6 (7) |
C1—N1—C4—C3 | −0.2 (10) | C16—N7—C12—N6 | 165.1 (6) |
C1—N1—C4—C11 | 174.3 (7) | Co1—N7—C12—N6 | −20.1 (9) |
N2—C3—C4—N1 | −1.1 (11) | C16—N7—C12—C13 | −7.1 (9) |
C5—C3—C4—N1 | −179.2 (6) | Co1—N7—C12—C13 | 167.8 (5) |
N2—C3—C4—C11 | −176.5 (6) | C11—N6—C12—N7 | −5.7 (10) |
C5—C3—C4—C11 | 5.4 (7) | C11—N6—C12—C13 | 166.8 (6) |
C6—N3—C5—N5 | 13.9 (11) | N7—C12—C13—C14 | 4.1 (10) |
C6—N3—C5—C3 | −161.2 (6) | N6—C12—C13—C14 | −168.6 (6) |
C11—N5—C5—N3 | −174.4 (6) | C12—C13—C14—C15 | 2.9 (11) |
Co1—N5—C5—N3 | 3.4 (10) | C13—C14—C15—C16 | −6.7 (12) |
C11—N5—C5—C3 | 1.4 (7) | C12—N7—C16—C15 | 3.3 (10) |
Co1—N5—C5—C3 | 179.3 (4) | Co1—N7—C16—C15 | −171.8 (6) |
N2—C3—C5—N3 | −6.4 (11) | C14—C15—C16—N7 | 3.6 (11) |
C4—C3—C5—N3 | 171.6 (6) | O1—Cl1—O2—O2ii | −43 (7) |
N2—C3—C5—N5 | 177.6 (6) | O1ii—Cl1—O2—O2ii | 154 (5) |
C4—C3—C5—N5 | −4.4 (7) | O3—Cl1—O2—O2ii | −120 (6) |
C10—N4—C6—N3 | 163.4 (6) | O3ii—Cl1—O2—O2ii | 57 (5) |
Co1—N4—C6—N3 | −25.4 (10) | O2ii—Cl1—O2—O3 | 120 (6) |
C10—N4—C6—C7 | −8.6 (10) | O1—Cl1—O2—O3 | 77 (2) |
Co1—N4—C6—C7 | 162.6 (6) | O1ii—Cl1—O2—O3 | −85.8 (18) |
C5—N3—C6—N4 | −1.4 (11) | O3ii—Cl1—O2—O3 | 177.6 (4) |
C5—N3—C6—C7 | 170.9 (7) | O2ii—Cl1—O3—O2 | −36 (3) |
N4—C6—C7—C8 | 4.0 (13) | O1—Cl1—O3—O2 | −143.4 (14) |
N3—C6—C7—C8 | −168.7 (8) | O1ii—Cl1—O3—O2 | 107.5 (13) |
C6—C7—C8—C9 | 2.2 (14) | O2ii—O2—O3—Cl1 | 55 (4) |
C7—C8—C9—C10 | −3.4 (14) |
Symmetry codes: (i) −x+1/2, y, −z+3/4; (ii) −x, −y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···N8 | 0.93 | 2.61 | 3.372 (12) | 139 |
C14—H14···O1iii | 0.93 | 2.55 | 3.256 (13) | 133 |
C16—H16···O3iv | 0.93 | 2.51 | 3.213 (19) | 133 |
C18—H18C···O2 | 0.96 | 2.42 | 3.31 (3) | 154 |
Symmetry codes: (iii) x, −y+1/2, −z+1/4; (iv) y, x+1/2, z+1/4. |
Funding information
We are grateful to the Swiss National Science Foundation and the University of Neuchâtel for financial support.
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