metal-organic compounds
Bis(benzo-15-crown-5-κ5O)barium tetrakis(isothiocyanato-κN)cobaltate(II)
aDepartment of Physics & Nano Technology, SRM Institute of Science and Technology, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai-603 203 Tamil Nadu, India, and bNanophotonics Laboratory, School of Physics, Bharathidasan University, Tiruchirappalli, Tamil Nadu, India, 620 024.
*Correspondence e-mail: rameshmano1980@gmail.com, phdguna@gmail.com
The title compound, [Ba(C14H20O5)2][Co(NCS)4], is formed by discrete anions and cations. The molecular packing is controlled by weak C—H⋯π interactions.
Keywords: dibenzo 15-Crown-5 ether; cobalt thiocyanide; catalysis and electrolyte; crystal structure.
CCDC reference: 1966145
Structure description
15-Crown-5 ether derivatives are used in the electronics industry, in et al., 2011), toxic metal sequestration and as battery electrolytes (Ligon et al., 2004).
(AlasundkarThe geometric parameters of the title compound (Fig. 1) agree well with those of reported similar structures (Cao et al., 2010; Vafaee et al., 2012; Ramesh et al., 2019). The CoII atom is surrounded by four N atoms and the BaII ion is coordinated by ten O atoms from two dibenzo-15-crown ligands in a sandwich-like configuration. Weak C—H⋯π interactions [C8⋯Cg1i = 3.760 (7) Å, H8A⋯Cg1i = 2.82 Å; C13⋯Cg2ii = 3.546 (6) Å, H13A⋯Cg2ii = 2.74 Å, Cg1 and Cg2 are the centroids of the C15–C20 and C1–C6 rings, respectively; symmetry codes: (i) − x, + y, − z; (ii) 1 − x, 1 − y, 1 − z] stabilize the crystal.
Synthesis and crystallization
Cobalt(II) chloride (0.25 mmol, 59.49 mg) and ammonium thiocyanate (1 mmol, 76.12 mg) were dissolved in deionized (DI) water. An aqueous solution (5 ml) of barium(II) chloride (0.25 mmol, 52.07 mg) was added dropwise and the mixture was stirred for 3 h. Then a 1,2-dichloroethane solution (10 ml) of benzo-15-crown-5 (0.5 mmol, 134.15 mg) was added dropwise. Finally, the solution was filtered using Whatman filter paper and the clear solution was held at room temperature for about 15 days when transparent blue crystals were obtained.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 1Structural data
CCDC reference: 1966145
https://doi.org/10.1107/S2414314621000249/bt4105sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314621000249/bt4105Isup2.hkl
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2020).[Ba(C14H20O5)2][Co(NCS)4] | F(000) = 1948 |
Mr = 965.19 | Dx = 1.545 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 12.0501 (19) Å | Cell parameters from 8674 reflections |
b = 20.208 (3) Å | θ = 1.6–26.6° |
c = 17.367 (3) Å | µ = 1.60 mm−1 |
β = 101.052 (4)° | T = 296 K |
V = 4150.6 (11) Å3 | Block, blue |
Z = 4 | 0.20 × 0.20 × 0.15 mm |
Bruker APEXII CCD diffractometer | 6117 reflections with I > 2σ(I) |
ω and φ scans | Rint = 0.065 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 26.6°, θmin = 1.6° |
Tmin = 0.734, Tmax = 0.787 | h = −15→15 |
62475 measured reflections | k = −25→25 |
8674 independent reflections | l = −21→21 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0375P)2 + 5.4623P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
8674 reflections | Δρmax = 0.62 e Å−3 |
469 parameters | Δρmin = −0.54 e Å−3 |
24 restraints |
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. The H atoms were positioned geometrically and refined using a riding model with C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for CH2 and C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for CH. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.3225 (6) | 0.4533 (3) | 0.4357 (3) | 0.0824 (19) | |
C2 | 0.2934 (7) | 0.4214 (4) | 0.5002 (4) | 0.129 (3) | |
H2 | 0.333921 | 0.385141 | 0.523499 | 0.155* | |
C3 | 0.1987 (9) | 0.4469 (5) | 0.5287 (5) | 0.130 (4) | |
H3 | 0.173072 | 0.426837 | 0.570131 | 0.156* | |
C4 | 0.1461 (9) | 0.5031 (7) | 0.4921 (7) | 0.173 (6) | |
H4 | 0.086649 | 0.521102 | 0.512321 | 0.207* | |
C5 | 0.1753 (6) | 0.5334 (5) | 0.4292 (5) | 0.135 (3) | |
H5 | 0.136534 | 0.570588 | 0.406899 | 0.162* | |
C6 | 0.2646 (5) | 0.5074 (4) | 0.3992 (4) | 0.0873 (19) | |
C7 | 0.2550 (5) | 0.5918 (3) | 0.2971 (5) | 0.110 (2) | |
H7A | 0.243978 | 0.625561 | 0.334624 | 0.132* | |
H7B | 0.182835 | 0.582531 | 0.263286 | 0.132* | |
C8 | 0.3400 (6) | 0.6148 (3) | 0.2491 (5) | 0.115 (2) | |
H8A | 0.315582 | 0.656205 | 0.222892 | 0.138* | |
H8B | 0.413232 | 0.621721 | 0.282665 | 0.138* | |
C9 | 0.4405 (7) | 0.5831 (3) | 0.1506 (4) | 0.111 (2) | |
H9A | 0.428222 | 0.557825 | 0.102204 | 0.133* | |
H9B | 0.436920 | 0.629714 | 0.136848 | 0.133* | |
C10 | 0.5539 (7) | 0.5679 (4) | 0.1962 (4) | 0.115 (2) | |
H10A | 0.610700 | 0.575690 | 0.164558 | 0.138* | |
H10B | 0.570379 | 0.596120 | 0.242193 | 0.138* | |
C11 | 0.6627 (4) | 0.4851 (4) | 0.2663 (4) | 0.097 (2) | |
H11A | 0.677081 | 0.512469 | 0.313037 | 0.117* | |
H11B | 0.722755 | 0.492800 | 0.237311 | 0.117* | |
C12 | 0.6620 (5) | 0.4151 (4) | 0.2888 (5) | 0.107 (2) | |
H12A | 0.655492 | 0.388075 | 0.241988 | 0.128* | |
H12B | 0.733691 | 0.404552 | 0.322601 | 0.128* | |
C13 | 0.5984 (5) | 0.4072 (3) | 0.4104 (3) | 0.0935 (18) | |
H13A | 0.625692 | 0.451895 | 0.422542 | 0.112* | |
H13B | 0.657747 | 0.376773 | 0.433564 | 0.112* | |
C14 | 0.5007 (6) | 0.3960 (3) | 0.4438 (4) | 0.0953 (18) | |
H14A | 0.481154 | 0.349386 | 0.441194 | 0.114* | |
H14B | 0.514924 | 0.409652 | 0.498369 | 0.114* | |
C15 | 0.3350 (4) | 0.2725 (2) | 0.3200 (3) | 0.0579 (12) | |
C16 | 0.3861 (5) | 0.2228 (3) | 0.3700 (4) | 0.0824 (17) | |
H16 | 0.451338 | 0.201879 | 0.361345 | 0.099* | |
C17 | 0.3369 (7) | 0.2053 (3) | 0.4331 (4) | 0.102 (2) | |
H17 | 0.370996 | 0.173143 | 0.468060 | 0.123* | |
C18 | 0.2403 (7) | 0.2342 (4) | 0.4446 (4) | 0.101 (2) | |
H18 | 0.207014 | 0.220258 | 0.485946 | 0.122* | |
C19 | 0.1900 (5) | 0.2845 (3) | 0.3955 (3) | 0.0780 (16) | |
H19 | 0.124790 | 0.305232 | 0.404520 | 0.094* | |
C20 | 0.2381 (4) | 0.3031 (2) | 0.3334 (3) | 0.0546 (11) | |
C21 | 0.0868 (4) | 0.3802 (2) | 0.2793 (3) | 0.0643 (12) | |
H21A | 0.089826 | 0.414993 | 0.318184 | 0.077* | |
H21B | 0.035533 | 0.346017 | 0.290289 | 0.077* | |
C22 | 0.0484 (4) | 0.4072 (3) | 0.1993 (3) | 0.0686 (13) | |
H22A | 0.041586 | 0.371700 | 0.161025 | 0.082* | |
H22B | −0.025130 | 0.427863 | 0.195347 | 0.082* | |
C23 | 0.1058 (4) | 0.4772 (3) | 0.1035 (3) | 0.0768 (15) | |
H23A | 0.141414 | 0.519944 | 0.100539 | 0.092* | |
H23B | 0.024920 | 0.482872 | 0.086384 | 0.092* | |
C24 | 0.1482 (4) | 0.4301 (3) | 0.0501 (3) | 0.0731 (14) | |
H24A | 0.112403 | 0.387229 | 0.051869 | 0.088* | |
H24B | 0.130626 | 0.446292 | −0.003450 | 0.088* | |
C25 | 0.3166 (5) | 0.3807 (3) | 0.0265 (3) | 0.0721 (14) | |
H25A | 0.305917 | 0.398026 | −0.026431 | 0.087* | |
H25B | 0.281135 | 0.337440 | 0.024656 | 0.087* | |
C26 | 0.4403 (4) | 0.3751 (3) | 0.0607 (3) | 0.0729 (14) | |
H26A | 0.475369 | 0.345295 | 0.028689 | 0.088* | |
H26B | 0.475374 | 0.418199 | 0.059655 | 0.088* | |
C27 | 0.4552 (4) | 0.2808 (2) | 0.1461 (3) | 0.0676 (13) | |
H27A | 0.516820 | 0.260792 | 0.125836 | 0.081* | |
H27B | 0.384545 | 0.264631 | 0.115474 | 0.081* | |
C28 | 0.4632 (4) | 0.2623 (2) | 0.2285 (3) | 0.0691 (13) | |
H28A | 0.454499 | 0.214804 | 0.233253 | 0.083* | |
H28B | 0.536094 | 0.275077 | 0.258992 | 0.083* | |
C29 | 0.4800 (5) | 0.7298 (2) | 0.3803 (4) | 0.0736 (15) | |
C30 | 0.8498 (4) | 0.6363 (3) | 0.2821 (5) | 0.090 (2) | |
C31 | 0.6233 (5) | 0.7841 (4) | 0.1279 (4) | 0.096 (2) | |
C32 | 0.7502 (4) | 0.8760 (2) | 0.3929 (3) | 0.0555 (11) | |
Ba1 | 0.36293 (2) | 0.43398 (2) | 0.23540 (2) | 0.04227 (9) | |
Co1 | 0.68526 (6) | 0.74686 (4) | 0.30213 (5) | 0.0757 (2) | |
N1 | 0.5546 (4) | 0.7252 (3) | 0.3488 (4) | 0.0995 (18) | |
N2 | 0.7929 (4) | 0.6751 (2) | 0.3021 (3) | 0.0913 (16) | |
N3 | 0.6391 (5) | 0.7691 (3) | 0.1925 (4) | 0.112 (2) | |
N4 | 0.7438 (4) | 0.8265 (2) | 0.3593 (3) | 0.0687 (11) | |
O1 | 0.3025 (3) | 0.5312 (2) | 0.3380 (2) | 0.0879 (12) | |
O2 | 0.3470 (4) | 0.56720 (17) | 0.1957 (3) | 0.0924 (14) | |
O3 | 0.5554 (3) | 0.5029 (2) | 0.2185 (2) | 0.0908 (12) | |
O4 | 0.5746 (3) | 0.3984 (2) | 0.3277 (2) | 0.0893 (12) | |
O5 | 0.4133 (3) | 0.43300 (18) | 0.4009 (2) | 0.0773 (10) | |
O6 | 0.1977 (2) | 0.35324 (14) | 0.28096 (18) | 0.0567 (8) | |
O7 | 0.1287 (2) | 0.45466 (15) | 0.1839 (2) | 0.0607 (8) | |
O8 | 0.2672 (3) | 0.42416 (15) | 0.07515 (19) | 0.0626 (8) | |
O9 | 0.4602 (2) | 0.35127 (15) | 0.13931 (19) | 0.0591 (8) | |
O10 | 0.3744 (3) | 0.29628 (15) | 0.2560 (2) | 0.0620 (8) | |
S1 | 0.37560 (12) | 0.73425 (7) | 0.42525 (10) | 0.0830 (4) | |
S2 | 0.92911 (16) | 0.58114 (9) | 0.2533 (2) | 0.1581 (12) | |
S3 | 0.5997 (2) | 0.80848 (15) | 0.03857 (12) | 0.1449 (9) | |
S4 | 0.76171 (14) | 0.94434 (7) | 0.44060 (10) | 0.0824 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.104 (5) | 0.101 (5) | 0.051 (3) | −0.056 (4) | 0.037 (3) | −0.032 (3) |
C2 | 0.157 (7) | 0.152 (7) | 0.087 (5) | −0.096 (6) | 0.049 (5) | −0.059 (5) |
C3 | 0.136 (8) | 0.183 (10) | 0.086 (6) | −0.091 (7) | 0.061 (6) | −0.050 (6) |
C4 | 0.109 (8) | 0.279 (16) | 0.149 (11) | −0.091 (9) | 0.071 (7) | −0.093 (10) |
C5 | 0.069 (4) | 0.206 (9) | 0.136 (7) | −0.011 (5) | 0.033 (5) | −0.087 (7) |
C6 | 0.055 (3) | 0.106 (5) | 0.103 (5) | −0.006 (3) | 0.022 (3) | −0.040 (4) |
C7 | 0.075 (4) | 0.062 (4) | 0.182 (7) | 0.027 (3) | −0.003 (4) | −0.045 (4) |
C8 | 0.109 (5) | 0.058 (4) | 0.157 (7) | 0.010 (3) | −0.028 (4) | 0.001 (4) |
C9 | 0.148 (5) | 0.093 (5) | 0.089 (5) | −0.048 (4) | 0.014 (4) | 0.035 (4) |
C10 | 0.132 (5) | 0.124 (6) | 0.090 (5) | −0.064 (5) | 0.025 (4) | 0.009 (4) |
C11 | 0.043 (3) | 0.149 (5) | 0.102 (5) | −0.028 (3) | 0.019 (3) | −0.033 (4) |
C12 | 0.058 (3) | 0.143 (5) | 0.119 (6) | −0.003 (4) | 0.017 (4) | −0.036 (5) |
C13 | 0.089 (4) | 0.101 (4) | 0.073 (4) | 0.011 (3) | −0.029 (3) | −0.016 (3) |
C14 | 0.112 (4) | 0.090 (4) | 0.072 (4) | 0.012 (4) | −0.014 (3) | 0.002 (3) |
C15 | 0.068 (3) | 0.042 (2) | 0.059 (3) | −0.010 (2) | 0.000 (2) | 0.006 (2) |
C16 | 0.093 (4) | 0.053 (3) | 0.088 (4) | −0.004 (3) | −0.015 (3) | 0.018 (3) |
C17 | 0.125 (6) | 0.084 (4) | 0.082 (5) | −0.026 (4) | −0.021 (4) | 0.046 (4) |
C18 | 0.131 (6) | 0.102 (5) | 0.065 (4) | −0.042 (5) | 0.004 (4) | 0.026 (4) |
C19 | 0.094 (4) | 0.077 (4) | 0.064 (3) | −0.028 (3) | 0.017 (3) | 0.008 (3) |
C20 | 0.063 (3) | 0.045 (2) | 0.053 (3) | −0.016 (2) | 0.005 (2) | 0.003 (2) |
C21 | 0.046 (2) | 0.064 (3) | 0.088 (3) | −0.006 (2) | 0.024 (2) | −0.006 (2) |
C22 | 0.037 (2) | 0.070 (3) | 0.096 (3) | −0.005 (2) | 0.006 (2) | 0.004 (3) |
C23 | 0.059 (3) | 0.062 (3) | 0.100 (4) | 0.007 (2) | −0.008 (3) | 0.032 (3) |
C24 | 0.062 (3) | 0.075 (3) | 0.071 (3) | −0.005 (2) | −0.015 (2) | 0.026 (2) |
C25 | 0.086 (3) | 0.080 (4) | 0.050 (3) | −0.015 (3) | 0.012 (3) | 0.001 (3) |
C26 | 0.075 (3) | 0.077 (3) | 0.073 (4) | −0.016 (3) | 0.030 (3) | −0.008 (3) |
C27 | 0.061 (3) | 0.063 (3) | 0.079 (3) | 0.006 (2) | 0.014 (3) | −0.022 (2) |
C28 | 0.065 (3) | 0.053 (3) | 0.087 (3) | 0.016 (2) | 0.011 (3) | −0.007 (3) |
C29 | 0.060 (3) | 0.048 (3) | 0.109 (5) | −0.005 (2) | 0.004 (3) | −0.009 (3) |
C30 | 0.050 (3) | 0.059 (3) | 0.164 (7) | −0.014 (3) | 0.025 (3) | −0.012 (4) |
C31 | 0.071 (4) | 0.127 (6) | 0.091 (5) | −0.001 (4) | 0.017 (4) | −0.060 (5) |
C32 | 0.052 (3) | 0.059 (3) | 0.055 (3) | 0.001 (2) | 0.011 (2) | 0.011 (2) |
Ba1 | 0.03838 (13) | 0.03676 (13) | 0.05013 (15) | −0.00420 (10) | 0.00463 (10) | −0.00217 (11) |
Co1 | 0.0583 (4) | 0.0668 (4) | 0.1027 (6) | −0.0035 (3) | 0.0174 (4) | −0.0230 (4) |
N1 | 0.069 (3) | 0.086 (4) | 0.149 (5) | −0.022 (3) | 0.037 (3) | −0.038 (3) |
N2 | 0.065 (3) | 0.065 (3) | 0.146 (5) | −0.005 (2) | 0.026 (3) | −0.016 (3) |
N3 | 0.094 (4) | 0.133 (5) | 0.103 (4) | 0.026 (3) | 0.003 (4) | −0.045 (4) |
N4 | 0.075 (3) | 0.058 (3) | 0.076 (3) | −0.012 (2) | 0.021 (2) | −0.005 (2) |
O1 | 0.088 (3) | 0.093 (3) | 0.082 (3) | 0.039 (2) | 0.015 (2) | −0.012 (2) |
O2 | 0.110 (3) | 0.047 (2) | 0.099 (3) | −0.014 (2) | −0.032 (2) | 0.011 (2) |
O3 | 0.084 (3) | 0.093 (3) | 0.102 (3) | −0.038 (2) | 0.033 (2) | −0.014 (2) |
O4 | 0.052 (2) | 0.118 (3) | 0.093 (3) | 0.014 (2) | 0.001 (2) | −0.026 (2) |
O5 | 0.092 (3) | 0.081 (2) | 0.055 (2) | 0.020 (2) | 0.0056 (19) | 0.0089 (18) |
O6 | 0.0497 (17) | 0.0530 (17) | 0.070 (2) | 0.0003 (14) | 0.0181 (15) | 0.0139 (15) |
O7 | 0.0429 (16) | 0.0508 (17) | 0.084 (2) | −0.0001 (13) | 0.0014 (16) | 0.0086 (16) |
O8 | 0.0623 (19) | 0.065 (2) | 0.0551 (19) | −0.0068 (16) | −0.0013 (15) | 0.0067 (16) |
O9 | 0.0550 (18) | 0.0599 (19) | 0.063 (2) | −0.0028 (15) | 0.0122 (15) | −0.0126 (16) |
O10 | 0.0638 (19) | 0.0465 (17) | 0.078 (2) | 0.0162 (14) | 0.0207 (17) | 0.0085 (16) |
S1 | 0.0646 (8) | 0.0724 (9) | 0.1137 (13) | 0.0111 (7) | 0.0210 (8) | 0.0001 (8) |
S2 | 0.0730 (11) | 0.0722 (11) | 0.345 (4) | −0.0107 (8) | 0.0797 (17) | −0.0492 (16) |
S3 | 0.1433 (19) | 0.208 (3) | 0.0861 (14) | −0.0415 (18) | 0.0277 (13) | −0.0441 (15) |
S4 | 0.0922 (10) | 0.0656 (9) | 0.0870 (10) | 0.0076 (7) | 0.0114 (8) | −0.0161 (7) |
C1—C6 | 1.383 (9) | C20—O6 | 1.386 (5) |
C1—C2 | 1.393 (9) | C21—O6 | 1.439 (5) |
C1—O5 | 1.409 (7) | C21—C22 | 1.482 (7) |
C2—C3 | 1.424 (12) | C21—H21A | 0.9700 |
C2—H2 | 0.9300 | C21—H21B | 0.9700 |
C3—C4 | 1.392 (14) | C22—O7 | 1.424 (5) |
C3—H3 | 0.9300 | C22—H22A | 0.9700 |
C4—C5 | 1.356 (13) | C22—H22B | 0.9700 |
C4—H4 | 0.9300 | C23—O7 | 1.443 (6) |
C5—C6 | 1.386 (9) | C23—C24 | 1.487 (8) |
C5—H5 | 0.9300 | C23—H23A | 0.9700 |
C6—O1 | 1.325 (8) | C23—H23B | 0.9700 |
C7—O1 | 1.476 (7) | C24—O8 | 1.421 (6) |
C7—C8 | 1.512 (10) | C24—H24A | 0.9700 |
C7—H7A | 0.9700 | C24—H24B | 0.9700 |
C7—H7B | 0.9700 | C25—O8 | 1.426 (6) |
C8—O2 | 1.350 (8) | C25—C26 | 1.500 (7) |
C8—H8A | 0.9700 | C25—H25A | 0.9700 |
C8—H8B | 0.9700 | C25—H25B | 0.9700 |
C9—C10 | 1.474 (10) | C26—O9 | 1.423 (6) |
C9—O2 | 1.525 (8) | C26—H26A | 0.9700 |
C9—H9A | 0.9700 | C26—H26B | 0.9700 |
C9—H9B | 0.9700 | C27—O9 | 1.431 (6) |
C10—O3 | 1.368 (7) | C27—C28 | 1.464 (7) |
C10—H10A | 0.9700 | C27—H27A | 0.9700 |
C10—H10B | 0.9700 | C27—H27B | 0.9700 |
C11—O3 | 1.442 (7) | C28—O10 | 1.428 (5) |
C11—C12 | 1.468 (10) | C28—H28A | 0.9700 |
C11—H11A | 0.9700 | C28—H28B | 0.9700 |
C11—H11B | 0.9700 | C29—N1 | 1.142 (7) |
C12—O4 | 1.397 (7) | C29—S1 | 1.606 (6) |
C12—H12A | 0.9700 | C30—N2 | 1.138 (7) |
C12—H12B | 0.9700 | C30—S2 | 1.609 (7) |
C13—O4 | 1.422 (7) | C31—N3 | 1.142 (9) |
C13—C14 | 1.428 (9) | C31—S3 | 1.600 (9) |
C13—H13A | 0.9700 | C32—N4 | 1.153 (6) |
C13—H13B | 0.9700 | C32—S4 | 1.603 (5) |
C14—O5 | 1.386 (6) | Ba1—O3 | 2.769 (4) |
C14—H14A | 0.9700 | Ba1—O9 | 2.776 (3) |
C14—H14B | 0.9700 | Ba1—O2 | 2.776 (3) |
C15—O10 | 1.376 (5) | Ba1—O6 | 2.803 (3) |
C15—C20 | 1.379 (7) | Ba1—O10 | 2.806 (3) |
C15—C16 | 1.392 (6) | Ba1—O8 | 2.808 (3) |
C16—C17 | 1.388 (9) | Ba1—O5 | 2.821 (3) |
C16—H16 | 0.9300 | Ba1—O7 | 2.824 (3) |
C17—C18 | 1.351 (10) | Ba1—O4 | 2.832 (3) |
C17—H17 | 0.9300 | Ba1—O1 | 2.839 (4) |
C18—C19 | 1.390 (8) | Co1—N3 | 1.932 (7) |
C18—H18 | 0.9300 | Co1—N2 | 1.947 (5) |
C19—C20 | 1.371 (7) | Co1—N4 | 1.950 (4) |
C19—H19 | 0.9300 | Co1—N1 | 1.953 (5) |
C6—C1—C2 | 123.4 (7) | O8—C25—H25B | 110.1 |
C6—C1—O5 | 113.5 (5) | C26—C25—H25B | 110.1 |
C2—C1—O5 | 123.1 (8) | H25A—C25—H25B | 108.4 |
C1—C2—C3 | 117.0 (9) | O9—C26—C25 | 112.2 (4) |
C1—C2—H2 | 121.5 | O9—C26—H26A | 109.2 |
C3—C2—H2 | 121.5 | C25—C26—H26A | 109.2 |
C4—C3—C2 | 117.5 (9) | O9—C26—H26B | 109.2 |
C4—C3—H3 | 121.2 | C25—C26—H26B | 109.2 |
C2—C3—H3 | 121.2 | H26A—C26—H26B | 107.9 |
C5—C4—C3 | 124.7 (11) | O9—C27—C28 | 109.9 (4) |
C5—C4—H4 | 117.7 | O9—C27—H27A | 109.7 |
C3—C4—H4 | 117.7 | C28—C27—H27A | 109.7 |
C4—C5—C6 | 118.2 (11) | O9—C27—H27B | 109.7 |
C4—C5—H5 | 120.9 | C28—C27—H27B | 109.7 |
C6—C5—H5 | 120.9 | H27A—C27—H27B | 108.2 |
O1—C6—C1 | 115.7 (5) | O10—C28—C27 | 106.8 (4) |
O1—C6—C5 | 125.1 (8) | O10—C28—H28A | 110.4 |
C1—C6—C5 | 119.1 (8) | C27—C28—H28A | 110.4 |
O1—C7—C8 | 106.3 (5) | O10—C28—H28B | 110.4 |
O1—C7—H7A | 110.5 | C27—C28—H28B | 110.4 |
C8—C7—H7A | 110.5 | H28A—C28—H28B | 108.6 |
O1—C7—H7B | 110.5 | N1—C29—S1 | 178.6 (6) |
C8—C7—H7B | 110.5 | N2—C30—S2 | 179.5 (7) |
H7A—C7—H7B | 108.7 | N3—C31—S3 | 177.3 (7) |
O2—C8—C7 | 107.3 (6) | N4—C32—S4 | 178.8 (5) |
O2—C8—H8A | 110.3 | O3—Ba1—O9 | 77.29 (11) |
C7—C8—H8A | 110.3 | O3—Ba1—O2 | 60.35 (14) |
O2—C8—H8B | 110.3 | O9—Ba1—O2 | 116.84 (13) |
C7—C8—H8B | 110.3 | O3—Ba1—O6 | 167.84 (11) |
H8A—C8—H8B | 108.5 | O9—Ba1—O6 | 102.94 (9) |
C10—C9—O2 | 112.3 (5) | O2—Ba1—O6 | 128.00 (12) |
C10—C9—H9A | 109.2 | O3—Ba1—O10 | 119.38 (11) |
O2—C9—H9A | 109.2 | O9—Ba1—O10 | 57.53 (9) |
C10—C9—H9B | 109.2 | O2—Ba1—O10 | 173.07 (11) |
O2—C9—H9B | 109.2 | O6—Ba1—O10 | 53.62 (9) |
H9A—C9—H9B | 107.9 | O3—Ba1—O8 | 97.11 (11) |
O3—C10—C9 | 108.3 (5) | O9—Ba1—O8 | 60.15 (10) |
O3—C10—H10A | 110.0 | O2—Ba1—O8 | 80.01 (11) |
C9—C10—H10A | 110.0 | O6—Ba1—O8 | 93.41 (9) |
O3—C10—H10B | 110.0 | O10—Ba1—O8 | 93.27 (9) |
C9—C10—H10B | 110.0 | O3—Ba1—O5 | 95.21 (12) |
H10A—C10—H10B | 108.4 | O9—Ba1—O5 | 125.10 (10) |
O3—C11—C12 | 110.1 (5) | O2—Ba1—O5 | 104.54 (12) |
O3—C11—H11A | 109.6 | O6—Ba1—O5 | 74.58 (11) |
C12—C11—H11A | 109.6 | O10—Ba1—O5 | 82.38 (10) |
O3—C11—H11B | 109.6 | O8—Ba1—O5 | 167.53 (11) |
C12—C11—H11B | 109.6 | O3—Ba1—O7 | 134.32 (12) |
H11A—C11—H11B | 108.2 | O9—Ba1—O7 | 114.23 (9) |
O4—C12—C11 | 113.8 (6) | O2—Ba1—O7 | 76.15 (11) |
O4—C12—H12A | 108.8 | O6—Ba1—O7 | 56.94 (9) |
C11—C12—H12A | 108.8 | O10—Ba1—O7 | 102.06 (9) |
O4—C12—H12B | 108.8 | O8—Ba1—O7 | 60.04 (10) |
C11—C12—H12B | 108.8 | O5—Ba1—O7 | 109.30 (11) |
H12A—C12—H12B | 107.7 | O3—Ba1—O4 | 60.39 (14) |
O4—C13—C14 | 111.6 (5) | O9—Ba1—O4 | 75.46 (10) |
O4—C13—H13A | 109.3 | O2—Ba1—O4 | 113.47 (12) |
C14—C13—H13A | 109.3 | O6—Ba1—O4 | 107.70 (11) |
O4—C13—H13B | 109.3 | O10—Ba1—O4 | 70.08 (11) |
C14—C13—H13B | 109.3 | O8—Ba1—O4 | 134.20 (11) |
H13A—C13—H13B | 108.0 | O5—Ba1—O4 | 55.06 (11) |
O5—C14—C13 | 107.3 (5) | O7—Ba1—O4 | 162.51 (11) |
O5—C14—H14A | 110.3 | O3—Ba1—O1 | 92.27 (13) |
C13—C14—H14A | 110.3 | O9—Ba1—O1 | 169.33 (11) |
O5—C14—H14B | 110.3 | O2—Ba1—O1 | 58.08 (14) |
C13—C14—H14B | 110.3 | O6—Ba1—O1 | 86.79 (12) |
H14A—C14—H14B | 108.5 | O10—Ba1—O1 | 128.21 (12) |
O10—C15—C20 | 114.5 (4) | O8—Ba1—O1 | 124.38 (10) |
O10—C15—C16 | 125.1 (5) | O5—Ba1—O1 | 52.89 (11) |
C20—C15—C16 | 120.4 (5) | O7—Ba1—O1 | 74.65 (10) |
C17—C16—C15 | 118.1 (6) | O4—Ba1—O1 | 97.59 (11) |
C17—C16—H16 | 120.9 | N3—Co1—N2 | 103.8 (2) |
C15—C16—H16 | 120.9 | N3—Co1—N4 | 108.5 (2) |
C18—C17—C16 | 121.2 (6) | N2—Co1—N4 | 116.05 (19) |
C18—C17—H17 | 119.4 | N3—Co1—N1 | 111.0 (3) |
C16—C17—H17 | 119.4 | N2—Co1—N1 | 115.1 (2) |
C17—C18—C19 | 120.7 (6) | N4—Co1—N1 | 102.42 (19) |
C17—C18—H18 | 119.6 | C29—N1—Co1 | 162.1 (5) |
C19—C18—H18 | 119.6 | C30—N2—Co1 | 162.5 (6) |
C20—C19—C18 | 118.9 (6) | C31—N3—Co1 | 172.9 (7) |
C20—C19—H19 | 120.5 | C32—N4—Co1 | 163.0 (4) |
C18—C19—H19 | 120.5 | C6—O1—C7 | 121.8 (5) |
C19—C20—C15 | 120.6 (5) | C6—O1—Ba1 | 114.9 (4) |
C19—C20—O6 | 124.7 (5) | C7—O1—Ba1 | 113.2 (4) |
C15—C20—O6 | 114.8 (4) | C8—O2—C9 | 110.6 (5) |
O6—C21—C22 | 106.2 (4) | C8—O2—Ba1 | 122.1 (4) |
O6—C21—H21A | 110.5 | C9—O2—Ba1 | 108.0 (4) |
C22—C21—H21A | 110.5 | C10—O3—C11 | 111.4 (5) |
O6—C21—H21B | 110.5 | C10—O3—Ba1 | 123.1 (4) |
C22—C21—H21B | 110.5 | C11—O3—Ba1 | 119.3 (4) |
H21A—C21—H21B | 108.7 | C12—O4—C13 | 115.6 (5) |
O7—C22—C21 | 108.8 (4) | C12—O4—Ba1 | 110.3 (4) |
O7—C22—H22A | 109.9 | C13—O4—Ba1 | 121.7 (3) |
C21—C22—H22A | 109.9 | C14—O5—C1 | 119.9 (5) |
O7—C22—H22B | 109.9 | C14—O5—Ba1 | 123.0 (4) |
C21—C22—H22B | 109.9 | C1—O5—Ba1 | 113.7 (3) |
H22A—C22—H22B | 108.3 | C20—O6—C21 | 119.9 (4) |
O7—C23—C24 | 112.1 (4) | C20—O6—Ba1 | 115.5 (2) |
O7—C23—H23A | 109.2 | C21—O6—Ba1 | 118.8 (2) |
C24—C23—H23A | 109.2 | C22—O7—C23 | 112.5 (4) |
O7—C23—H23B | 109.2 | C22—O7—Ba1 | 121.0 (3) |
C24—C23—H23B | 109.2 | C23—O7—Ba1 | 110.3 (3) |
H23A—C23—H23B | 107.9 | C24—O8—C25 | 112.4 (4) |
O8—C24—C23 | 108.0 (4) | C24—O8—Ba1 | 119.8 (3) |
O8—C24—H24A | 110.1 | C25—O8—Ba1 | 119.4 (3) |
C23—C24—H24A | 110.1 | C26—O9—C27 | 114.5 (4) |
O8—C24—H24B | 110.1 | C26—O9—Ba1 | 111.1 (3) |
C23—C24—H24B | 110.1 | C27—O9—Ba1 | 121.3 (3) |
H24A—C24—H24B | 108.4 | C15—O10—C28 | 119.9 (4) |
O8—C25—C26 | 108.0 (4) | C15—O10—Ba1 | 115.6 (3) |
O8—C25—H25A | 110.1 | C28—O10—Ba1 | 117.2 (3) |
C26—C25—H25A | 110.1 |
Acknowledgements
The authors acknowledge the SAIF, IIT Madras, Chennai, India for the data collection.
References
Alasundkar, K. N., Deshmukh, M. B., Salunkhe, D. K. & Sankpal, S. A. (2011). Der Chemica Sinica, 2, 118–124. CAS Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cao, Z., Liu, K., Niu, M. & Wang, D. (2010). Acta Cryst. E66, m68. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ligon, S. C., Topping, C. M., Jin, J., Fallis, S., Irvin, J. A., Desmarteau, D. D. & Smith, D. W. (2004). Macromol. Chem. Phys. 205, 801–805. Web of Science CrossRef CAS Google Scholar
Ramesh, V., Rajarajan, K. & Gunasekaran, B. (2019). IUCrData, 4, x190888. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Vafaee, M., Amini, M. M. & Ng, S. W. (2012). Acta Cryst. E68, m213. Web of Science CSD CrossRef IUCr Journals Google Scholar
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