metal-organic compounds
Di-μ-aqua-bis[aqua(2,2′-bipyridine)(4-nitrobenzoato)cobalt(II)] bis(4-nitrobenzoate)
aSchool of Chemical Sciences, Goa University, Goa 403206, India
*Correspondence e-mail: sndhuri@unigoa.ac.in
The title compound, [Co2(C7H4NO4)2(C10H8N2)2(H2O)4](C7H4NO4)2, consists of a centrosymmetric bimetallic complex charge-balanced by free 4-nitrobenzoate anions. The CoII ion exhibits a distorted cis-CoN2O4 octahedral coordination environment and the Co⋯Co separation is 3.326 (2) Å. In the crystal, the dications and anions are linked by O—H⋯O and C—H⋯O hydrogen bonds.
CCDC reference: 2009578
Structure description
As part of an ongoing research program we are investigating the structural aspects of mixed-ligand compounds of divalent-metal 4-nitrobenzoates. Recently we described the structure of [Co(H2O)2(DMSO)2(C7H4NO4)](C7H4NO4) 2 (DMSO = dimethylsulfoxide; C7H4NO4 = 4-nitrobenzoate) containing a bidentate as well as a free 4-nitrobenzoate anion (Srinivasan et al., 2020). Our attempts to replace the cis-aqua ligands of 2 with 2,2′-bipyridine has resulted in the isolation of the diaqua-bridged title dinuclear compound. The Cambridge Structural Database (CSD, version 5.40, update September 2019; Groom et al., 2016) lists the structures of several cobalt 4-nitrobenzoates: of these, more than a dozen are mononuclear cobalt compounds (Srinivasan et al., 2004, 2020; Chakravorty et al., 2011) while only four dinuclear compounds of 4-nitrobenzoate are known to date (Singh et al., 2007; Jung et al., 2009; Yang et al., 2011; Wang & Qi, 2014). The title compound is a new addition to the list of dimeric cobalt 4-nitrobenzoates.
The structure of the title compound, 1, consists of a crystallographically unique cobaltous ion and a 2,2′-bipyridine molecule, two crystallographically independent 4-nitrobenzoate ions and two unique aqua ligands (one terminal, one bridging). The CoII ion, one 4-nitrobenzoate ion, one 2,2′-bipyridine molecule and each of a terminal and bridging water molecule build up one half of a dimeric dicationic species [Co2(H2O)2(C10H8N2)2(C7H4NO4)2(μ2-H2O)2]2+, the other half being generated by inversion symmetry (Fig. 1). The crystallographic inversion centre is situated at the midpoint of the line connecting the CoII atoms in the dimer. A charge-balancing 4-nitrobenzoate ion completes the structure.
In the centrosymmetric dimer, each CoII ion exhibits a distorted octahedral environment and is bonded to a terminal aqua ligand, a monodentate 4-nitrobenzoate ligand disposed cis to the terminal aqua ligand and a bidentate 2,2′-bipyridine molecule. A pair of cis-aqua ligands bridges the metal centres and completes the hexa-coordination around the metal ions resulting in a Co⋯Co(1 – x, 1 – y, 1 – z) separation of 3.326 (2) Å. It is interesting to note that in three of the four known dinuclear cobalt compounds (Singh et al., 2007; Yang et al., 2011; Wang & Qi, 2014), the 4-nitrobenzoate anion functions as a monodentate ligand as in the title compound. One example each of a dinuclear (Jung et al., 2009) and a tetranuclear cobalt compound (Dimitrou et al., 2001) is known where the 4-nitrobenzoate ion functions as a symmetric bridging ligand.
The geometric parameters of 1 are in their normal ranges and are in agreement with reported data (Srinivasan et al., 2020). The Co—Ow (w = water) bonds [2.0743 (10) and 2.1617 (9) Å] are elongated as compared to the Co—Oc (c = carboxylate) distance, which is the shortest at 2.0494 (9) Å. The cis-O—Co—O and N—Co—N bond angles range between 77.97 (4) and 100.02 (4)°, while the trans bond angles deviate from ideal values, indicating a distortion of the {CoN2O4} octahedron.
All of the H atoms attached to the aqua ligands, and five of the other H atoms viz. H9, H14, H16, H17 and H21 bonded to C9, C14, C16, C17 and C21, respectively, function as hydrogen-bond donors, while the oxygen atoms O2, O3, O5, O6 and O7 of the 4-nitrobenzoate ions function as acceptors, resulting in a total of four O—H⋯O and five C—H⋯O hydrogen bonds (Table 1). Each free 4-nitrobenzoate anion is linked with four symmetry-related dications with the aid of two O—H⋯O hydrogen bonds and four C—H⋯O hydrogen bonds (Figs. 2 and 3). Each of the dinuclear dicobalt dicationic species is linked with two symmetry-related dications and eight symmetry-generated anions (Fig. 4), resulting in a three-dimensional supramolecular network.
Synthesis and crystallization
Crystals of 2 (0.0292 g, 0.05 mmol) were taken in DMSO (3 ml) to obtain a purple solution. 2,2′-Bipyridine (0.0078 g, 0.05 mmol) was dissolved in DMSO (3 ml) in a separate beaker and then was added dropwise to the cobalt solution with continuous swirling. The pale-orange solution thus obtained was left undisturbed at room temperature. After to days, dark-orange blocks of 1 started forming in the solution, which were isolated by filtration and air dried. Yield 60%.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
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Structural data
CCDC reference: 2009578
https://doi.org/10.1107/S2414314620007968/hb4348sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620007968/hb4348Isup2.hkl
Data collection: APEX3 (Bruker, 2019); cell
SAINT (Bruker, 2019); data reduction: SAINT (Bruker, 2019); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: shelXle (Hübschle et al., 2011).[Co2(C7H4NO4)2(C10H8N2)2(H2O)4](C7H4NO4)2 | Z = 1 |
Mr = 1166.74 | F(000) = 598 |
Triclinic, P1 | Dx = 1.662 Mg m−3 |
a = 7.2747 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.4927 (8) Å | Cell parameters from 9978 reflections |
c = 16.3560 (12) Å | θ = 2.9–28.2° |
α = 97.735 (2)° | µ = 0.81 mm−1 |
β = 102.840 (2)° | T = 296 K |
γ = 102.607 (2)° | Block, orange |
V = 1165.70 (15) Å3 | 0.45 × 0.32 × 0.21 mm |
Bruker D8 Quest eco diffractometer | 5312 reflections with I > 2σ(I) |
Radiation source: Sealed Tube | Rint = 0.025 |
φ and ω scans | θmax = 28.3°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −9→9 |
k = −13→13 | |
26747 measured reflections | l = −21→21 |
5763 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.025 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.064 | w = 1/[σ2(Fo2) + (0.0255P)2 + 0.6838P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.003 |
5763 reflections | Δρmax = 0.36 e Å−3 |
368 parameters | Δρmin = −0.31 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Co1 | 0.43361 (2) | 0.63922 (2) | 0.52457 (2) | 0.01063 (5) | |
O1 | 0.43137 (17) | 0.71403 (11) | 1.06326 (6) | 0.0261 (2) | |
N1 | 0.32901 (17) | 0.60682 (12) | 1.01984 (7) | 0.0180 (2) | |
C1 | 0.32850 (19) | 0.57702 (13) | 0.92928 (8) | 0.0147 (2) | |
O2 | 0.22558 (18) | 0.52407 (11) | 1.04780 (7) | 0.0289 (2) | |
N2 | 0.61203 (16) | 0.83416 (10) | 0.57038 (7) | 0.0131 (2) | |
C2 | 0.45366 (19) | 0.66787 (13) | 0.89966 (8) | 0.0168 (3) | |
H2 | 0.539777 | 0.742960 | 0.936466 | 0.020* | |
O3 | 0.19021 (13) | 0.40968 (9) | 0.61539 (6) | 0.01502 (18) | |
N3 | 0.44762 (16) | 0.70799 (11) | 0.41050 (7) | 0.0130 (2) | |
C3 | 0.44682 (19) | 0.64358 (13) | 0.81350 (8) | 0.0161 (2) | |
H3 | 0.529735 | 0.703100 | 0.792083 | 0.019* | |
O4 | 0.43133 (13) | 0.59742 (9) | 0.64323 (6) | 0.01478 (18) | |
N4 | 0.82411 (18) | 0.08005 (12) | −0.06413 (8) | 0.0207 (2) | |
C4 | 0.31743 (18) | 0.53122 (12) | 0.75861 (8) | 0.0129 (2) | |
C5 | 0.1950 (2) | 0.44082 (13) | 0.79086 (8) | 0.0169 (3) | |
H5 | 0.109775 | 0.365050 | 0.754405 | 0.020* | |
O5 | 1.07575 (15) | 0.36007 (10) | 0.32867 (6) | 0.0211 (2) | |
C6 | 0.1994 (2) | 0.46313 (13) | 0.87707 (8) | 0.0180 (3) | |
H6 | 0.118041 | 0.403405 | 0.899036 | 0.022* | |
O6 | 0.85644 (15) | 0.18061 (9) | 0.33776 (6) | 0.0203 (2) | |
C7 | 0.31025 (18) | 0.51044 (12) | 0.66454 (8) | 0.0127 (2) | |
O7 | 0.91826 (18) | 0.15271 (12) | −0.10126 (7) | 0.0317 (3) | |
C8 | 0.6889 (2) | 0.89288 (13) | 0.65249 (8) | 0.0167 (3) | |
H8 | 0.650756 | 0.848993 | 0.694104 | 0.020* | |
O8 | 0.70001 (17) | −0.02340 (11) | −0.10076 (7) | 0.0297 (2) | |
C9 | 0.8231 (2) | 1.01652 (13) | 0.67843 (9) | 0.0188 (3) | |
H9 | 0.874547 | 1.054302 | 0.736112 | 0.023* | |
C10 | 0.8785 (2) | 1.08205 (13) | 0.61629 (9) | 0.0191 (3) | |
H10 | 0.967902 | 1.164988 | 0.631700 | 0.023* | |
C11 | 0.79935 (19) | 1.02285 (13) | 0.53093 (9) | 0.0165 (2) | |
H11 | 0.834491 | 1.065696 | 0.488378 | 0.020* | |
C12 | 0.66666 (18) | 0.89850 (12) | 0.50973 (8) | 0.0131 (2) | |
C13 | 0.57188 (18) | 0.82847 (12) | 0.41994 (8) | 0.0130 (2) | |
C14 | 0.6047 (2) | 0.88285 (13) | 0.34951 (9) | 0.0176 (3) | |
H14 | 0.691802 | 0.965414 | 0.356946 | 0.021* | |
C15 | 0.5048 (2) | 0.81138 (14) | 0.26838 (9) | 0.0206 (3) | |
H15 | 0.525861 | 0.845041 | 0.220521 | 0.025* | |
C16 | 0.3734 (2) | 0.68944 (14) | 0.25880 (9) | 0.0188 (3) | |
H16 | 0.302949 | 0.641070 | 0.204804 | 0.023* | |
C17 | 0.34957 (19) | 0.64140 (13) | 0.33163 (8) | 0.0155 (2) | |
H17 | 0.261827 | 0.559500 | 0.325489 | 0.019* | |
C18 | 0.95292 (19) | 0.24975 (13) | 0.29757 (8) | 0.0146 (2) | |
C19 | 0.92261 (19) | 0.20072 (13) | 0.20274 (8) | 0.0149 (2) | |
C20 | 1.03275 (19) | 0.27527 (13) | 0.15766 (9) | 0.0173 (3) | |
H20 | 1.127507 | 0.352694 | 0.186407 | 0.021* | |
O1W | 0.16527 (15) | 0.68171 (11) | 0.51582 (7) | 0.0186 (2) | |
C21 | 1.0024 (2) | 0.23507 (14) | 0.07020 (9) | 0.0189 (3) | |
H21 | 1.075168 | 0.284846 | 0.039878 | 0.023* | |
C22 | 0.8611 (2) | 0.11911 (13) | 0.02938 (9) | 0.0178 (3) | |
C23 | 0.7511 (2) | 0.04133 (14) | 0.07225 (9) | 0.0218 (3) | |
H23 | 0.658049 | −0.036827 | 0.043395 | 0.026* | |
C24 | 0.7839 (2) | 0.08360 (14) | 0.15973 (9) | 0.0203 (3) | |
H24 | 0.712092 | 0.032818 | 0.189930 | 0.024* | |
O2W | 0.30828 (13) | 0.43132 (9) | 0.47476 (6) | 0.01185 (17) | |
H1A | 0.148 (3) | 0.718 (2) | 0.5594 (15) | 0.042 (6)* | |
H1B | 0.066 (3) | 0.650 (2) | 0.4773 (14) | 0.039 (6)* | |
H2A | 0.264 (3) | 0.410 (2) | 0.5123 (15) | 0.045 (6)* | |
H2B | 0.223 (3) | 0.404 (2) | 0.4276 (14) | 0.039 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.01158 (9) | 0.01116 (8) | 0.00889 (8) | 0.00091 (6) | 0.00424 (6) | 0.00170 (6) |
O1 | 0.0363 (6) | 0.0240 (5) | 0.0128 (5) | 0.0000 (5) | 0.0064 (4) | −0.0016 (4) |
N1 | 0.0228 (6) | 0.0209 (6) | 0.0115 (5) | 0.0064 (5) | 0.0061 (4) | 0.0034 (4) |
C1 | 0.0187 (6) | 0.0180 (6) | 0.0092 (6) | 0.0061 (5) | 0.0056 (5) | 0.0031 (5) |
O2 | 0.0405 (6) | 0.0285 (6) | 0.0170 (5) | −0.0013 (5) | 0.0154 (5) | 0.0056 (4) |
N2 | 0.0144 (5) | 0.0128 (5) | 0.0126 (5) | 0.0034 (4) | 0.0045 (4) | 0.0024 (4) |
C2 | 0.0173 (6) | 0.0177 (6) | 0.0128 (6) | 0.0004 (5) | 0.0037 (5) | 0.0011 (5) |
O3 | 0.0163 (4) | 0.0161 (4) | 0.0111 (4) | 0.0010 (3) | 0.0048 (3) | 0.0008 (3) |
N3 | 0.0136 (5) | 0.0141 (5) | 0.0118 (5) | 0.0033 (4) | 0.0047 (4) | 0.0025 (4) |
C3 | 0.0166 (6) | 0.0180 (6) | 0.0130 (6) | 0.0003 (5) | 0.0061 (5) | 0.0032 (5) |
O4 | 0.0174 (4) | 0.0162 (4) | 0.0112 (4) | 0.0019 (4) | 0.0065 (3) | 0.0032 (3) |
N4 | 0.0239 (6) | 0.0204 (6) | 0.0168 (6) | 0.0057 (5) | 0.0054 (5) | 0.0002 (5) |
C4 | 0.0139 (6) | 0.0156 (6) | 0.0108 (6) | 0.0051 (5) | 0.0049 (4) | 0.0028 (5) |
C5 | 0.0200 (6) | 0.0154 (6) | 0.0135 (6) | 0.0003 (5) | 0.0063 (5) | 0.0008 (5) |
O5 | 0.0234 (5) | 0.0185 (5) | 0.0136 (5) | −0.0051 (4) | −0.0005 (4) | 0.0027 (4) |
C6 | 0.0230 (7) | 0.0176 (6) | 0.0141 (6) | 0.0014 (5) | 0.0092 (5) | 0.0041 (5) |
O6 | 0.0241 (5) | 0.0161 (4) | 0.0205 (5) | −0.0001 (4) | 0.0116 (4) | 0.0012 (4) |
C7 | 0.0139 (6) | 0.0154 (6) | 0.0109 (6) | 0.0056 (5) | 0.0053 (4) | 0.0037 (5) |
O7 | 0.0416 (7) | 0.0307 (6) | 0.0202 (5) | −0.0008 (5) | 0.0134 (5) | 0.0028 (5) |
C8 | 0.0194 (6) | 0.0161 (6) | 0.0143 (6) | 0.0047 (5) | 0.0046 (5) | 0.0016 (5) |
O8 | 0.0345 (6) | 0.0258 (5) | 0.0202 (5) | −0.0017 (5) | 0.0046 (5) | −0.0046 (4) |
C9 | 0.0200 (6) | 0.0174 (6) | 0.0156 (6) | 0.0047 (5) | 0.0011 (5) | −0.0023 (5) |
C10 | 0.0165 (6) | 0.0137 (6) | 0.0240 (7) | 0.0017 (5) | 0.0038 (5) | −0.0003 (5) |
C11 | 0.0163 (6) | 0.0135 (6) | 0.0199 (6) | 0.0024 (5) | 0.0065 (5) | 0.0036 (5) |
C12 | 0.0126 (6) | 0.0133 (6) | 0.0141 (6) | 0.0038 (5) | 0.0042 (5) | 0.0026 (5) |
C13 | 0.0125 (6) | 0.0130 (5) | 0.0134 (6) | 0.0027 (4) | 0.0041 (5) | 0.0022 (5) |
C14 | 0.0194 (6) | 0.0159 (6) | 0.0173 (6) | 0.0008 (5) | 0.0069 (5) | 0.0047 (5) |
C15 | 0.0271 (7) | 0.0216 (7) | 0.0138 (6) | 0.0032 (6) | 0.0079 (5) | 0.0064 (5) |
C16 | 0.0234 (7) | 0.0194 (6) | 0.0125 (6) | 0.0036 (5) | 0.0050 (5) | 0.0025 (5) |
C17 | 0.0174 (6) | 0.0138 (6) | 0.0135 (6) | 0.0009 (5) | 0.0045 (5) | 0.0014 (5) |
C18 | 0.0140 (6) | 0.0137 (6) | 0.0155 (6) | 0.0039 (5) | 0.0030 (5) | 0.0024 (5) |
C19 | 0.0137 (6) | 0.0146 (6) | 0.0161 (6) | 0.0037 (5) | 0.0033 (5) | 0.0024 (5) |
C20 | 0.0149 (6) | 0.0162 (6) | 0.0178 (6) | −0.0001 (5) | 0.0036 (5) | 0.0013 (5) |
O1W | 0.0149 (5) | 0.0254 (5) | 0.0154 (5) | 0.0058 (4) | 0.0049 (4) | 0.0004 (4) |
C21 | 0.0190 (6) | 0.0185 (6) | 0.0188 (7) | 0.0015 (5) | 0.0071 (5) | 0.0039 (5) |
C22 | 0.0199 (6) | 0.0178 (6) | 0.0153 (6) | 0.0055 (5) | 0.0047 (5) | 0.0003 (5) |
C23 | 0.0242 (7) | 0.0156 (6) | 0.0194 (7) | −0.0032 (5) | 0.0044 (5) | −0.0018 (5) |
C24 | 0.0235 (7) | 0.0159 (6) | 0.0183 (7) | −0.0019 (5) | 0.0068 (5) | 0.0013 (5) |
O2W | 0.0120 (4) | 0.0137 (4) | 0.0085 (4) | 0.0000 (3) | 0.0036 (3) | 0.0012 (3) |
Co1—O4 | 2.0494 (9) | C8—H8 | 0.9300 |
Co1—O1W | 2.0743 (10) | C9—C10 | 1.385 (2) |
Co1—N2 | 2.1038 (11) | C9—H9 | 0.9300 |
Co1—N3 | 2.1039 (11) | C10—C11 | 1.386 (2) |
Co1—O2W | 2.1394 (9) | C10—H10 | 0.9300 |
Co1—O2Wi | 2.1617 (9) | C11—C12 | 1.3908 (17) |
O1—N1 | 1.2282 (16) | C11—H11 | 0.9300 |
N1—O2 | 1.2262 (15) | C12—C13 | 1.4868 (18) |
N1—C1 | 1.4712 (16) | C13—C14 | 1.3960 (18) |
C1—C2 | 1.3833 (18) | C14—C15 | 1.3845 (19) |
C1—C6 | 1.3851 (19) | C14—H14 | 0.9300 |
N2—C8 | 1.3376 (17) | C15—C16 | 1.3861 (19) |
N2—C12 | 1.3550 (16) | C15—H15 | 0.9300 |
C2—C3 | 1.3857 (18) | C16—C17 | 1.3851 (18) |
C2—H2 | 0.9300 | C16—H16 | 0.9300 |
O3—C7 | 1.2581 (16) | C17—H17 | 0.9300 |
N3—C17 | 1.3386 (16) | C18—C19 | 1.5176 (18) |
N3—C13 | 1.3511 (16) | C19—C24 | 1.3906 (18) |
C3—C4 | 1.3918 (18) | C19—C20 | 1.3934 (18) |
C3—H3 | 0.9300 | C20—C21 | 1.3890 (19) |
O4—C7 | 1.2655 (15) | C20—H20 | 0.9300 |
N4—O7 | 1.2251 (16) | O1W—H1A | 0.81 (2) |
N4—O8 | 1.2284 (16) | O1W—H1B | 0.82 (2) |
N4—C22 | 1.4763 (17) | C21—C22 | 1.3831 (19) |
C4—C5 | 1.3951 (17) | C21—H21 | 0.9300 |
C4—C7 | 1.5121 (17) | C22—C23 | 1.3844 (19) |
C5—C6 | 1.3900 (18) | C23—C24 | 1.390 (2) |
C5—H5 | 0.9300 | C23—H23 | 0.9300 |
O5—C18 | 1.2590 (16) | C24—H24 | 0.9300 |
C6—H6 | 0.9300 | O2W—H2A | 0.79 (2) |
O6—C18 | 1.2499 (16) | O2W—H2B | 0.84 (2) |
C8—C9 | 1.3897 (19) | ||
O4—Co1—O1W | 88.78 (4) | C9—C10—C11 | 119.35 (12) |
O4—Co1—N2 | 95.06 (4) | C9—C10—H10 | 120.3 |
O1W—Co1—N2 | 98.21 (4) | C11—C10—H10 | 120.3 |
O4—Co1—N3 | 172.65 (4) | C10—C11—C12 | 119.11 (12) |
O1W—Co1—N3 | 89.91 (4) | C10—C11—H11 | 120.4 |
N2—Co1—N3 | 77.97 (4) | C12—C11—H11 | 120.4 |
O4—Co1—O2W | 87.29 (4) | N2—C12—C11 | 121.70 (12) |
O1W—Co1—O2W | 93.78 (4) | N2—C12—C13 | 115.43 (11) |
N2—Co1—O2W | 167.83 (4) | C11—C12—C13 | 122.86 (12) |
N3—Co1—O2W | 100.02 (4) | N3—C13—C14 | 121.59 (12) |
O4—Co1—O2Wi | 91.60 (4) | N3—C13—C12 | 115.34 (11) |
O1W—Co1—O2Wi | 172.46 (4) | C14—C13—C12 | 123.07 (11) |
N2—Co1—O2Wi | 89.26 (4) | C15—C14—C13 | 118.67 (12) |
N3—Co1—O2Wi | 90.64 (4) | C15—C14—H14 | 120.7 |
O2W—Co1—O2Wi | 78.72 (4) | C13—C14—H14 | 120.7 |
O2—N1—O1 | 123.42 (12) | C14—C15—C16 | 119.70 (12) |
O2—N1—C1 | 118.33 (11) | C14—C15—H15 | 120.2 |
O1—N1—C1 | 118.23 (11) | C16—C15—H15 | 120.2 |
C2—C1—C6 | 123.04 (12) | C17—C16—C15 | 118.36 (13) |
C2—C1—N1 | 117.76 (12) | C17—C16—H16 | 120.8 |
C6—C1—N1 | 119.15 (11) | C15—C16—H16 | 120.8 |
C8—N2—C12 | 118.50 (11) | N3—C17—C16 | 122.72 (12) |
C8—N2—Co1 | 126.05 (9) | N3—C17—H17 | 118.6 |
C12—N2—Co1 | 115.11 (8) | C16—C17—H17 | 118.6 |
C1—C2—C3 | 117.98 (12) | O6—C18—O5 | 125.68 (12) |
C1—C2—H2 | 121.0 | O6—C18—C19 | 119.05 (12) |
C3—C2—H2 | 121.0 | O5—C18—C19 | 115.27 (11) |
C17—N3—C13 | 118.93 (11) | C24—C19—C20 | 119.42 (12) |
C17—N3—Co1 | 125.64 (9) | C24—C19—C18 | 120.96 (12) |
C13—N3—Co1 | 115.41 (8) | C20—C19—C18 | 119.60 (12) |
C2—C3—C4 | 120.82 (12) | C21—C20—C19 | 120.64 (12) |
C2—C3—H3 | 119.6 | C21—C20—H20 | 119.7 |
C4—C3—H3 | 119.6 | C19—C20—H20 | 119.7 |
C7—O4—Co1 | 129.34 (8) | Co1—O1W—H1A | 116.9 (15) |
O7—N4—O8 | 123.35 (12) | Co1—O1W—H1B | 127.0 (15) |
O7—N4—C22 | 118.32 (12) | H1A—O1W—H1B | 114 (2) |
O8—N4—C22 | 118.33 (12) | C22—C21—C20 | 118.29 (13) |
C3—C4—C5 | 119.66 (12) | C22—C21—H21 | 120.9 |
C3—C4—C7 | 119.19 (11) | C20—C21—H21 | 120.9 |
C5—C4—C7 | 121.15 (11) | C21—C22—C23 | 122.70 (13) |
C6—C5—C4 | 120.51 (12) | C21—C22—N4 | 117.93 (12) |
C6—C5—H5 | 119.7 | C23—C22—N4 | 119.34 (12) |
C4—C5—H5 | 119.7 | C22—C23—C24 | 117.98 (13) |
C1—C6—C5 | 117.98 (12) | C22—C23—H23 | 121.0 |
C1—C6—H6 | 121.0 | C24—C23—H23 | 121.0 |
C5—C6—H6 | 121.0 | C23—C24—C19 | 120.94 (13) |
O3—C7—O4 | 126.09 (11) | C23—C24—H24 | 119.5 |
O3—C7—C4 | 118.54 (11) | C19—C24—H24 | 119.5 |
O4—C7—C4 | 115.36 (11) | Co1—O2W—Co1i | 101.28 (4) |
N2—C8—C9 | 122.98 (12) | Co1—O2W—H2A | 100.6 (16) |
N2—C8—H8 | 118.5 | Co1i—O2W—H2A | 110.0 (16) |
C9—C8—H8 | 118.5 | Co1—O2W—H2B | 121.6 (14) |
C10—C9—C8 | 118.37 (13) | Co1i—O2W—H2B | 112.2 (14) |
C10—C9—H9 | 120.8 | H2A—O2W—H2B | 110 (2) |
C8—C9—H9 | 120.8 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2W—H2B···O5ii | 0.84 (2) | 1.67 (2) | 2.5101 (13) | 173 (2) |
O2W—H2A···O3 | 0.79 (2) | 1.88 (2) | 2.6483 (13) | 164 (2) |
O1W—H1B···O3iii | 0.82 (2) | 2.04 (2) | 2.8477 (14) | 174 (2) |
O1W—H1A···O6i | 0.81 (2) | 1.88 (2) | 2.6803 (14) | 171 (2) |
C21—H21···O2iv | 0.93 | 2.48 | 3.2219 (17) | 137 |
C17—H17···O5ii | 0.93 | 2.24 | 3.1679 (16) | 172 |
C16—H16···O2v | 0.93 | 2.57 | 3.4644 (17) | 160 |
C14—H14···O6vi | 0.93 | 2.41 | 3.3126 (16) | 164 |
C9—H9···O7vii | 0.93 | 2.64 | 3.5467 (18) | 164 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z; (iii) −x, −y+1, −z+1; (iv) x+1, y, z−1; (v) x, y, z−1; (vi) x, y+1, z; (vii) x, y+1, z+1. |
Funding information
We thank Council of Scientific and Industrial Research (CSIR) New Delhi, for financial support.
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