metal-organic compounds
Tris[N-(2-furoyl)-N,N′-diphenylthioureato-κ2O,S]cobalt(III)
aDepartamento de Química Inorgánica, Facultad de Química, Universidad de la Habana, Habana 10400, Cuba, bGrupo de Cristalografía, Instituto de Física de São Carlos, Universidade de São Paulo, São Carlos, Brazil, cLaboratorio de Síntesis Orgánica, Facultad de Química, Universidad de la Habana, Habana 10400, Cuba, and dInstituto de Ciencia y Tecnología de Materiales, Universidad de la Habana, Habana 10400, Cuba
*Correspondence e-mail: hperez@fq.uh.cu
In the title compound, [Co(C18H13N2O2S)3], the CoIII atom is coordinated by the S and O atoms of three N-furoyl-N′,N′-diphenylthiourea ligands in a slightly distorted octahedral geometry. The three O atoms are arranged fac, as are the three S atoms.
Related literature
For general background, see: Arslan et al. (2003). For related structures, see: Jia et al. (2007); Pérez et al. (2008). For the synthesis of the ligand, see: Hernández et al. (2003).
Experimental
Crystal data
|
Refinement
|
|
Data collection: COLLECT (Nonius, 1998); cell DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
10.1107/S1600536808011598/hy2130sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808011598/hy2130Isup2.hkl
N-furoyl-N',N'-diphenylthiourea ligand was synthesized according to a procedure described by Hernández et al. (2003), by converting furoyl chloride into furoyl isothiocyanate and then condensing with an appropriate amine. To an ethanol solution (30 ml) containing the ligand (0.96 g, 3 mmol) was added an ethanol solution of Co(CH3COO)2.4H2O (0.25 g, 1 mmol). The solution was stirred at room temperature for 2 h, and at once a solution of NaOH (1 N) was added to adjust pH to the neutral value. The mixture was filtered and the filtrate was evaporated under reduced pressure to give a green solid, which was washed with acetone. Single crystals were obtained by slow evaporation of a chloroform/N,N-diphenylformamide solution (1:1, v/v) of the complex.
H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C).
Data collection: COLLECT (Nonius, 1998); cell
DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. View of the unit cell of the title complex. |
[Co(C18H13N2O2S)3] | Z = 2 |
Mr = 1023.05 | F(000) = 1056 |
Triclinic, P1 | Dx = 1.432 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.0236 (11) Å | Cell parameters from 8767 reflections |
b = 13.1438 (16) Å | θ = 2.9–25.4° |
c = 19.388 (3) Å | µ = 0.55 mm−1 |
α = 79.357 (7)° | T = 150 K |
β = 83.477 (8)° | Block, green |
γ = 71.152 (8)° | 0.15 × 0.13 × 0.02 mm |
V = 2371.8 (5) Å3 |
Nonius KappaCCD diffractometer | 4680 reflections with I > 2σ(I) |
ϕ and ω scans | Rint = 0.092 |
Absorption correction: gaussian (Coppens et al., 1965) | θmax = 25°, θmin = 3.0° |
Tmin = 0.955, Tmax = 0.980 | h = −11→11 |
13609 measured reflections | k = −15→14 |
8289 independent reflections | l = −23→23 |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.069P)2 + 0.4724P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.086 | (Δ/σ)max < 0.001 |
wR(F2) = 0.222 | Δρmax = 0.51 e Å−3 |
S = 1.19 | Δρmin = −0.53 e Å−3 |
8289 reflections | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
632 parameters | Extinction coefficient: 0.0076 (14) |
0 restraints |
[Co(C18H13N2O2S)3] | γ = 71.152 (8)° |
Mr = 1023.05 | V = 2371.8 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.0236 (11) Å | Mo Kα radiation |
b = 13.1438 (16) Å | µ = 0.55 mm−1 |
c = 19.388 (3) Å | T = 150 K |
α = 79.357 (7)° | 0.15 × 0.13 × 0.02 mm |
β = 83.477 (8)° |
Nonius KappaCCD diffractometer | 8289 independent reflections |
Absorption correction: gaussian (Coppens et al., 1965) | 4680 reflections with I > 2σ(I) |
Tmin = 0.955, Tmax = 0.980 | Rint = 0.092 |
13609 measured reflections |
R[F2 > 2σ(F2)] = 0.086 | 0 restraints |
wR(F2) = 0.222 | H-atom parameters constrained |
S = 1.19 | Δρmax = 0.51 e Å−3 |
8289 reflections | Δρmin = −0.53 e Å−3 |
632 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.8134 (7) | 0.8428 (6) | 0.3061 (3) | 0.0522 (17) | |
C2 | 0.6159 (7) | 0.8246 (6) | 0.2602 (4) | 0.0555 (18) | |
C3 | 0.8605 (7) | 0.9270 (6) | 0.3268 (4) | 0.0588 (19) | |
C4 | 0.7991 (8) | 1.0351 (6) | 0.3228 (4) | 0.066 (2) | |
H4 | 0.7102 | 1.0748 | 0.3068 | 0.079* | |
C5 | 0.8942 (10) | 1.0766 (8) | 0.3472 (5) | 0.089 (3) | |
H5 | 0.8798 | 1.149 | 0.3508 | 0.106* | |
C6 | 1.0102 (10) | 0.9925 (8) | 0.3645 (5) | 0.087 (3) | |
H6 | 1.0903 | 0.9976 | 0.3818 | 0.104* | |
C7 | 0.4392 (7) | 1.0014 (5) | 0.2305 (4) | 0.0562 (19) | |
C8 | 0.3801 (7) | 1.0434 (6) | 0.2904 (5) | 0.068 (2) | |
H8 | 0.3778 | 0.9973 | 0.3328 | 0.082* | |
C9 | 0.3241 (8) | 1.1545 (7) | 0.2874 (5) | 0.073 (2) | |
H9 | 0.2838 | 1.1836 | 0.3279 | 0.087* | |
C10 | 0.3278 (9) | 1.2218 (7) | 0.2253 (6) | 0.082 (3) | |
H10 | 0.2893 | 1.2969 | 0.223 | 0.099* | |
C11 | 0.3895 (9) | 1.1776 (7) | 0.1656 (5) | 0.076 (2) | |
H11 | 0.3928 | 1.2235 | 0.1231 | 0.091* | |
C12 | 0.4462 (8) | 1.0663 (6) | 0.1680 (4) | 0.062 (2) | |
H12 | 0.488 | 1.0367 | 0.1278 | 0.075* | |
C13 | 0.4055 (7) | 0.8386 (5) | 0.1994 (4) | 0.0556 (18) | |
C14 | 0.2771 (7) | 0.8351 (6) | 0.2318 (4) | 0.064 (2) | |
H14 | 0.2509 | 0.8556 | 0.2761 | 0.076* | |
C15 | 0.1880 (8) | 0.8017 (7) | 0.1994 (5) | 0.077 (2) | |
H15 | 0.1024 | 0.7974 | 0.2218 | 0.093* | |
C16 | 0.2263 (8) | 0.7744 (6) | 0.1329 (5) | 0.073 (2) | |
H16 | 0.1659 | 0.7529 | 0.1099 | 0.087* | |
C17 | 0.3530 (8) | 0.7791 (6) | 0.1013 (4) | 0.067 (2) | |
H17 | 0.3786 | 0.7603 | 0.0566 | 0.08* | |
C18 | 0.4443 (7) | 0.8113 (6) | 0.1343 (4) | 0.0613 (19) | |
H18 | 0.5307 | 0.8141 | 0.1123 | 0.074* | |
C19 | 0.8633 (7) | 0.7096 (5) | 0.1301 (4) | 0.0530 (17) | |
C20 | 0.8537 (6) | 0.5288 (5) | 0.1438 (4) | 0.0521 (17) | |
C21 | 0.8372 (7) | 0.8086 (5) | 0.0784 (4) | 0.0529 (17) | |
C22 | 0.7907 (8) | 0.8320 (6) | 0.0137 (4) | 0.064 (2) | |
H22 | 0.7667 | 0.7857 | −0.0101 | 0.077* | |
C23 | 0.7852 (9) | 0.9420 (6) | −0.0116 (5) | 0.076 (2) | |
H23 | 0.7561 | 0.9819 | −0.0551 | 0.091* | |
C24 | 0.8294 (8) | 0.9762 (7) | 0.0388 (4) | 0.070 (2) | |
H24 | 0.8379 | 1.0454 | 0.0355 | 0.084* | |
C25 | 0.7778 (7) | 0.4928 (6) | 0.0372 (4) | 0.0527 (17) | |
C26 | 0.6395 (7) | 0.5639 (6) | 0.0319 (4) | 0.065 (2) | |
H26 | 0.588 | 0.5922 | 0.0708 | 0.078* | |
C27 | 0.5821 (8) | 0.5905 (7) | −0.0333 (4) | 0.066 (2) | |
H27 | 0.4905 | 0.6376 | −0.038 | 0.079* | |
C28 | 0.6569 (8) | 0.5492 (6) | −0.0910 (4) | 0.067 (2) | |
H28 | 0.6169 | 0.5683 | −0.1344 | 0.081* | |
C29 | 0.7912 (7) | 0.4796 (6) | −0.0840 (4) | 0.0608 (19) | |
H29 | 0.842 | 0.4503 | −0.1227 | 0.073* | |
C30 | 0.8521 (7) | 0.4524 (6) | −0.0202 (4) | 0.0576 (18) | |
H30 | 0.9443 | 0.4062 | −0.0163 | 0.069* | |
C31 | 0.8687 (7) | 0.3430 (5) | 0.1307 (4) | 0.0546 (18) | |
C32 | 0.7627 (8) | 0.2952 (6) | 0.1373 (4) | 0.0598 (19) | |
H32 | 0.67 | 0.3382 | 0.1298 | 0.072* | |
C33 | 0.7944 (8) | 0.1840 (6) | 0.1550 (4) | 0.069 (2) | |
H33 | 0.7231 | 0.1521 | 0.1581 | 0.083* | |
C34 | 0.9307 (9) | 0.1195 (6) | 0.1682 (4) | 0.068 (2) | |
H34 | 0.9513 | 0.0445 | 0.1806 | 0.081* | |
C35 | 1.0364 (8) | 0.1675 (6) | 0.1628 (4) | 0.067 (2) | |
H35 | 1.1283 | 0.1248 | 0.1724 | 0.081* | |
C36 | 1.0056 (7) | 0.2786 (6) | 0.1432 (4) | 0.0593 (19) | |
H36 | 1.0775 | 0.3103 | 0.1383 | 0.071* | |
C37 | 1.1649 (7) | 0.4839 (6) | 0.3130 (4) | 0.0509 (17) | |
C38 | 1.0025 (7) | 0.4247 (6) | 0.3945 (4) | 0.0541 (18) | |
C39 | 1.3184 (7) | 0.4579 (6) | 0.2980 (4) | 0.0518 (17) | |
C40 | 1.4255 (8) | 0.3729 (6) | 0.3245 (4) | 0.0600 (19) | |
H40 | 1.4202 | 0.3139 | 0.3582 | 0.072* | |
C41 | 1.5501 (8) | 0.3934 (8) | 0.2891 (5) | 0.080 (3) | |
H41 | 1.6426 | 0.3489 | 0.2953 | 0.096* | |
C42 | 1.5094 (8) | 0.4877 (8) | 0.2457 (5) | 0.077 (3) | |
H42 | 1.57 | 0.52 | 0.2168 | 0.093* | |
C43 | 0.8608 (7) | 0.3438 (6) | 0.4858 (4) | 0.0571 (18) | |
C44 | 0.8498 (8) | 0.3463 (6) | 0.5573 (4) | 0.062 (2) | |
H44 | 0.9256 | 0.3484 | 0.5799 | 0.075* | |
C45 | 0.7243 (9) | 0.3454 (6) | 0.5943 (4) | 0.070 (2) | |
H45 | 0.7162 | 0.3463 | 0.6425 | 0.084* | |
C46 | 0.6115 (9) | 0.3433 (7) | 0.5617 (5) | 0.080 (2) | |
H46 | 0.5271 | 0.344 | 0.5873 | 0.096* | |
C47 | 0.6237 (9) | 0.3400 (8) | 0.4914 (5) | 0.088 (3) | |
H47 | 0.547 | 0.3383 | 0.4693 | 0.105* | |
C48 | 0.7462 (8) | 0.3392 (7) | 0.4529 (4) | 0.079 (2) | |
H48 | 0.7537 | 0.3355 | 0.4051 | 0.095* | |
C49 | 1.1159 (7) | 0.2534 (6) | 0.4715 (4) | 0.0565 (18) | |
C50 | 1.2270 (8) | 0.2720 (7) | 0.4956 (4) | 0.069 (2) | |
H50 | 1.2286 | 0.3428 | 0.494 | 0.083* | |
C51 | 1.3385 (9) | 0.1833 (9) | 0.5227 (5) | 0.087 (3) | |
H51 | 1.4146 | 0.1948 | 0.5398 | 0.104* | |
C52 | 1.3359 (11) | 0.0805 (9) | 0.5241 (5) | 0.099 (3) | |
H52 | 1.4103 | 0.0222 | 0.5429 | 0.119* | |
C53 | 1.2261 (12) | 0.0598 (8) | 0.4984 (5) | 0.099 (3) | |
H53 | 1.2264 | −0.0111 | 0.4985 | 0.119* | |
C54 | 1.1151 (9) | 0.1486 (7) | 0.4724 (4) | 0.074 (2) | |
H54 | 1.039 | 0.1372 | 0.4553 | 0.088* | |
N1 | 0.6891 (6) | 0.8853 (5) | 0.2768 (3) | 0.0576 (15) | |
N2 | 0.4907 (5) | 0.8844 (4) | 0.2321 (3) | 0.0546 (15) | |
N3 | 0.8304 (5) | 0.6293 (4) | 0.1078 (3) | 0.0515 (14) | |
N4 | 0.8344 (6) | 0.4568 (4) | 0.1060 (3) | 0.0549 (15) | |
N5 | 1.1304 (6) | 0.4083 (5) | 0.3616 (3) | 0.0549 (15) | |
N6 | 0.9923 (5) | 0.3427 (5) | 0.4472 (3) | 0.0543 (15) | |
O1 | 0.8953 (4) | 0.7458 (4) | 0.3172 (2) | 0.0539 (12) | |
O2 | 0.9919 (5) | 0.8962 (4) | 0.3525 (3) | 0.0744 (15) | |
O3 | 0.9116 (4) | 0.7098 (4) | 0.1875 (2) | 0.0517 (11) | |
O4 | 0.8609 (5) | 0.8976 (4) | 0.0959 (3) | 0.0662 (14) | |
O5 | 1.0897 (4) | 0.5727 (4) | 0.2805 (2) | 0.0533 (12) | |
O6 | 1.3660 (5) | 0.5297 (4) | 0.2500 (3) | 0.0701 (14) | |
S1 | 0.65537 (17) | 0.68586 (14) | 0.27060 (10) | 0.0546 (5) | |
S2 | 0.89274 (18) | 0.48093 (14) | 0.22979 (10) | 0.0528 (5) | |
S3 | 0.85482 (18) | 0.53514 (16) | 0.38161 (10) | 0.0602 (5) | |
Co1 | 0.88802 (9) | 0.62353 (7) | 0.27666 (5) | 0.0511 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.050 (4) | 0.064 (5) | 0.046 (4) | −0.018 (4) | −0.008 (3) | −0.015 (4) |
C2 | 0.049 (4) | 0.056 (4) | 0.060 (5) | −0.010 (3) | −0.011 (3) | −0.011 (4) |
C3 | 0.051 (4) | 0.072 (5) | 0.058 (5) | −0.019 (4) | −0.013 (4) | −0.015 (4) |
C4 | 0.064 (5) | 0.060 (5) | 0.080 (6) | −0.017 (4) | −0.013 (4) | −0.022 (4) |
C5 | 0.101 (7) | 0.073 (6) | 0.108 (8) | −0.034 (5) | −0.016 (6) | −0.033 (5) |
C6 | 0.087 (6) | 0.095 (7) | 0.105 (7) | −0.046 (6) | −0.010 (5) | −0.046 (6) |
C7 | 0.053 (4) | 0.042 (4) | 0.075 (5) | −0.007 (3) | −0.018 (4) | −0.017 (4) |
C8 | 0.062 (5) | 0.065 (5) | 0.077 (6) | −0.011 (4) | −0.009 (4) | −0.021 (4) |
C9 | 0.070 (5) | 0.066 (5) | 0.088 (7) | −0.019 (4) | 0.002 (5) | −0.033 (5) |
C10 | 0.081 (6) | 0.057 (5) | 0.114 (8) | −0.014 (4) | −0.036 (6) | −0.025 (6) |
C11 | 0.088 (6) | 0.058 (5) | 0.086 (7) | −0.024 (4) | −0.026 (5) | −0.006 (5) |
C12 | 0.073 (5) | 0.048 (4) | 0.070 (5) | −0.018 (4) | −0.019 (4) | −0.010 (4) |
C13 | 0.049 (4) | 0.047 (4) | 0.068 (5) | −0.009 (3) | −0.013 (4) | −0.008 (4) |
C14 | 0.056 (4) | 0.065 (5) | 0.075 (6) | −0.024 (4) | 0.001 (4) | −0.017 (4) |
C15 | 0.055 (5) | 0.068 (5) | 0.115 (8) | −0.022 (4) | −0.012 (5) | −0.018 (5) |
C16 | 0.058 (5) | 0.046 (4) | 0.118 (8) | −0.010 (3) | −0.030 (5) | −0.016 (5) |
C17 | 0.065 (5) | 0.060 (5) | 0.073 (6) | −0.006 (4) | −0.022 (4) | −0.016 (4) |
C18 | 0.050 (4) | 0.069 (5) | 0.069 (5) | −0.014 (3) | −0.007 (4) | −0.026 (4) |
C19 | 0.048 (4) | 0.051 (4) | 0.058 (5) | −0.013 (3) | −0.005 (3) | −0.007 (4) |
C20 | 0.044 (4) | 0.047 (4) | 0.067 (5) | −0.017 (3) | −0.003 (3) | −0.009 (4) |
C21 | 0.054 (4) | 0.050 (4) | 0.058 (5) | −0.019 (3) | −0.007 (3) | −0.009 (3) |
C22 | 0.075 (5) | 0.056 (5) | 0.063 (5) | −0.018 (4) | −0.022 (4) | −0.008 (4) |
C23 | 0.092 (6) | 0.058 (5) | 0.069 (6) | −0.011 (4) | −0.022 (5) | 0.001 (4) |
C24 | 0.088 (6) | 0.059 (5) | 0.063 (5) | −0.024 (4) | −0.007 (4) | −0.003 (4) |
C25 | 0.058 (4) | 0.054 (4) | 0.052 (4) | −0.019 (3) | −0.014 (3) | −0.011 (3) |
C26 | 0.054 (4) | 0.074 (5) | 0.066 (5) | −0.013 (4) | −0.011 (4) | −0.018 (4) |
C27 | 0.053 (4) | 0.083 (6) | 0.060 (5) | −0.012 (4) | −0.010 (4) | −0.020 (4) |
C28 | 0.071 (5) | 0.073 (5) | 0.065 (5) | −0.030 (4) | −0.014 (4) | −0.010 (4) |
C29 | 0.060 (4) | 0.062 (5) | 0.063 (5) | −0.016 (4) | −0.002 (4) | −0.024 (4) |
C30 | 0.053 (4) | 0.068 (5) | 0.054 (5) | −0.016 (3) | −0.007 (4) | −0.020 (4) |
C31 | 0.063 (4) | 0.048 (4) | 0.057 (5) | −0.016 (3) | −0.013 (4) | −0.013 (3) |
C32 | 0.056 (4) | 0.058 (5) | 0.071 (5) | −0.022 (4) | −0.013 (4) | −0.013 (4) |
C33 | 0.075 (5) | 0.067 (5) | 0.072 (6) | −0.029 (4) | −0.007 (4) | −0.014 (4) |
C34 | 0.081 (5) | 0.049 (4) | 0.075 (6) | −0.019 (4) | −0.007 (4) | −0.016 (4) |
C35 | 0.062 (5) | 0.050 (4) | 0.079 (6) | −0.001 (4) | −0.017 (4) | −0.006 (4) |
C36 | 0.057 (4) | 0.052 (4) | 0.067 (5) | −0.011 (3) | −0.012 (4) | −0.008 (4) |
C37 | 0.047 (4) | 0.058 (4) | 0.055 (4) | −0.022 (3) | −0.003 (3) | −0.018 (4) |
C38 | 0.043 (4) | 0.064 (5) | 0.059 (5) | −0.018 (3) | −0.008 (3) | −0.015 (4) |
C39 | 0.057 (4) | 0.054 (4) | 0.047 (4) | −0.020 (3) | 0.003 (3) | −0.012 (3) |
C40 | 0.062 (5) | 0.058 (5) | 0.060 (5) | −0.014 (4) | −0.019 (4) | −0.008 (4) |
C41 | 0.043 (4) | 0.100 (7) | 0.098 (7) | −0.004 (4) | −0.019 (5) | −0.037 (6) |
C42 | 0.044 (4) | 0.113 (7) | 0.089 (7) | −0.027 (5) | 0.005 (4) | −0.052 (6) |
C43 | 0.054 (4) | 0.065 (5) | 0.054 (5) | −0.025 (3) | 0.002 (4) | −0.007 (4) |
C44 | 0.063 (5) | 0.073 (5) | 0.055 (5) | −0.027 (4) | 0.005 (4) | −0.013 (4) |
C45 | 0.089 (6) | 0.078 (5) | 0.051 (5) | −0.033 (5) | 0.008 (4) | −0.025 (4) |
C46 | 0.066 (5) | 0.100 (7) | 0.081 (7) | −0.034 (5) | 0.006 (5) | −0.021 (5) |
C47 | 0.059 (5) | 0.136 (9) | 0.084 (7) | −0.050 (5) | 0.001 (5) | −0.022 (6) |
C48 | 0.069 (5) | 0.116 (7) | 0.070 (6) | −0.043 (5) | −0.012 (4) | −0.029 (5) |
C49 | 0.057 (4) | 0.051 (4) | 0.061 (5) | −0.014 (3) | −0.007 (4) | −0.011 (4) |
C50 | 0.065 (5) | 0.069 (5) | 0.070 (5) | −0.012 (4) | −0.011 (4) | −0.012 (4) |
C51 | 0.061 (5) | 0.103 (8) | 0.080 (6) | −0.008 (5) | −0.022 (4) | 0.004 (6) |
C52 | 0.079 (7) | 0.090 (8) | 0.091 (8) | 0.010 (6) | 0.010 (6) | 0.004 (6) |
C53 | 0.114 (8) | 0.066 (6) | 0.090 (7) | 0.006 (6) | 0.000 (6) | −0.008 (5) |
C54 | 0.082 (6) | 0.070 (5) | 0.070 (6) | −0.022 (5) | −0.005 (4) | −0.015 (4) |
N1 | 0.046 (3) | 0.058 (4) | 0.071 (4) | −0.012 (3) | −0.014 (3) | −0.015 (3) |
N2 | 0.042 (3) | 0.056 (4) | 0.072 (4) | −0.016 (3) | −0.015 (3) | −0.017 (3) |
N3 | 0.052 (3) | 0.048 (3) | 0.059 (4) | −0.016 (3) | −0.012 (3) | −0.013 (3) |
N4 | 0.060 (3) | 0.046 (3) | 0.062 (4) | −0.018 (3) | −0.011 (3) | −0.008 (3) |
N5 | 0.054 (3) | 0.054 (3) | 0.057 (4) | −0.017 (3) | −0.009 (3) | −0.008 (3) |
N6 | 0.048 (3) | 0.059 (4) | 0.057 (4) | −0.017 (3) | −0.008 (3) | −0.005 (3) |
O1 | 0.045 (2) | 0.057 (3) | 0.061 (3) | −0.011 (2) | −0.012 (2) | −0.016 (2) |
O2 | 0.062 (3) | 0.082 (4) | 0.089 (4) | −0.021 (3) | −0.010 (3) | −0.038 (3) |
O3 | 0.045 (2) | 0.058 (3) | 0.055 (3) | −0.015 (2) | −0.009 (2) | −0.014 (2) |
O4 | 0.073 (3) | 0.058 (3) | 0.072 (4) | −0.024 (3) | −0.012 (3) | −0.010 (3) |
O5 | 0.051 (3) | 0.056 (3) | 0.054 (3) | −0.013 (2) | −0.010 (2) | −0.011 (2) |
O6 | 0.059 (3) | 0.081 (4) | 0.077 (4) | −0.026 (3) | 0.000 (3) | −0.023 (3) |
S1 | 0.0444 (9) | 0.0532 (10) | 0.0670 (12) | −0.0134 (8) | −0.0088 (8) | −0.0113 (9) |
S2 | 0.0522 (10) | 0.0526 (10) | 0.0546 (11) | −0.0147 (8) | −0.0077 (8) | −0.0111 (8) |
S3 | 0.0510 (10) | 0.0651 (12) | 0.0587 (12) | −0.0097 (9) | −0.0024 (9) | −0.0108 (9) |
Co1 | 0.0441 (5) | 0.0536 (6) | 0.0563 (6) | −0.0120 (4) | −0.0081 (4) | −0.0130 (5) |
C1—O1 | 1.268 (8) | C28—H28 | 0.93 |
C1—N1 | 1.335 (8) | C29—C30 | 1.378 (9) |
C1—C3 | 1.468 (10) | C29—H29 | 0.93 |
C2—N1 | 1.343 (8) | C30—H30 | 0.93 |
C2—N2 | 1.361 (8) | C31—C36 | 1.381 (9) |
C2—S1 | 1.714 (7) | C31—C32 | 1.383 (9) |
C3—C4 | 1.344 (10) | C31—N4 | 1.423 (8) |
C3—O2 | 1.371 (8) | C32—C33 | 1.376 (10) |
C4—C5 | 1.402 (11) | C32—H32 | 0.93 |
C4—H4 | 0.93 | C33—C34 | 1.379 (10) |
C5—C6 | 1.344 (12) | C33—H33 | 0.93 |
C5—H5 | 0.93 | C34—C35 | 1.383 (10) |
C6—O2 | 1.400 (9) | C34—H34 | 0.93 |
C6—H6 | 0.93 | C35—C36 | 1.379 (9) |
C7—C12 | 1.356 (10) | C35—H35 | 0.93 |
C7—C8 | 1.370 (10) | C36—H36 | 0.93 |
C7—N2 | 1.451 (8) | C37—O5 | 1.263 (7) |
C8—C9 | 1.378 (10) | C37—N5 | 1.340 (8) |
C8—H8 | 0.93 | C37—C39 | 1.470 (9) |
C9—C10 | 1.361 (11) | C38—N5 | 1.335 (8) |
C9—H9 | 0.93 | C38—N6 | 1.362 (8) |
C10—C11 | 1.384 (12) | C38—S3 | 1.710 (7) |
C10—H10 | 0.93 | C39—C40 | 1.342 (9) |
C11—C12 | 1.382 (10) | C39—O6 | 1.361 (8) |
C11—H11 | 0.93 | C40—C41 | 1.434 (11) |
C12—H12 | 0.93 | C40—H40 | 0.93 |
C13—C18 | 1.356 (10) | C41—C42 | 1.333 (11) |
C13—C14 | 1.377 (9) | C41—H41 | 0.93 |
C13—N2 | 1.445 (8) | C42—O6 | 1.362 (8) |
C14—C15 | 1.368 (10) | C42—H42 | 0.93 |
C14—H14 | 0.93 | C43—C44 | 1.383 (10) |
C15—C16 | 1.380 (12) | C43—C48 | 1.399 (9) |
C15—H15 | 0.93 | C43—N6 | 1.437 (8) |
C16—C17 | 1.361 (11) | C44—C45 | 1.378 (10) |
C16—H16 | 0.93 | C44—H44 | 0.93 |
C17—C18 | 1.382 (10) | C45—C46 | 1.367 (10) |
C17—H17 | 0.93 | C45—H45 | 0.93 |
C18—H18 | 0.93 | C46—C47 | 1.362 (11) |
C19—O3 | 1.263 (8) | C46—H46 | 0.93 |
C19—N3 | 1.355 (9) | C47—C48 | 1.361 (11) |
C19—C21 | 1.458 (9) | C47—H47 | 0.93 |
C20—N3 | 1.336 (8) | C48—H48 | 0.93 |
C20—N4 | 1.370 (8) | C49—C50 | 1.362 (10) |
C20—S2 | 1.712 (7) | C49—C54 | 1.376 (10) |
C21—C22 | 1.336 (9) | C49—N6 | 1.458 (8) |
C21—O4 | 1.371 (8) | C50—C51 | 1.397 (10) |
C22—C23 | 1.423 (10) | C50—H50 | 0.93 |
C22—H22 | 0.93 | C51—C52 | 1.356 (13) |
C23—C24 | 1.320 (11) | C51—H51 | 0.93 |
C23—H23 | 0.93 | C52—C53 | 1.379 (14) |
C24—O4 | 1.356 (8) | C52—H52 | 0.93 |
C24—H24 | 0.93 | C53—C54 | 1.388 (14) |
C25—C30 | 1.360 (9) | C53—H53 | 0.93 |
C25—C26 | 1.402 (9) | C54—H54 | 0.93 |
C25—N4 | 1.444 (8) | O1—Co1 | 1.939 (5) |
C26—C27 | 1.387 (9) | O3—Co1 | 1.920 (5) |
C26—H26 | 0.93 | O5—Co1 | 1.919 (4) |
C27—C28 | 1.372 (10) | S1—Co1 | 2.217 (2) |
C27—H27 | 0.93 | S2—Co1 | 2.214 (2) |
C28—C29 | 1.366 (10) | S3—Co1 | 2.196 (2) |
O1—C1—N1 | 131.6 (7) | C33—C34—C35 | 119.3 (7) |
O1—C1—C3 | 116.8 (6) | C33—C34—H34 | 120.3 |
N1—C1—C3 | 111.5 (6) | C35—C34—H34 | 120.3 |
N1—C2—N2 | 113.6 (6) | C36—C35—C34 | 120.1 (7) |
N1—C2—S1 | 130.0 (5) | C36—C35—H35 | 120 |
N2—C2—S1 | 116.5 (5) | C34—C35—H35 | 120 |
C4—C3—O2 | 110.6 (7) | C35—C36—C31 | 120.4 (7) |
C4—C3—C1 | 131.4 (7) | C35—C36—H36 | 119.8 |
O2—C3—C1 | 117.9 (6) | C31—C36—H36 | 119.8 |
C3—C4—C5 | 107.1 (7) | O5—C37—N5 | 131.3 (6) |
C3—C4—H4 | 126.4 | O5—C37—C39 | 116.2 (6) |
C5—C4—H4 | 126.4 | N5—C37—C39 | 112.4 (6) |
C6—C5—C4 | 107.5 (8) | N5—C38—N6 | 114.3 (6) |
C6—C5—H5 | 126.3 | N5—C38—S3 | 129.0 (6) |
C4—C5—H5 | 126.3 | N6—C38—S3 | 116.7 (5) |
C5—C6—O2 | 109.5 (7) | C40—C39—O6 | 111.4 (6) |
C5—C6—H6 | 125.2 | C40—C39—C37 | 130.9 (7) |
O2—C6—H6 | 125.2 | O6—C39—C37 | 117.6 (6) |
C12—C7—C8 | 121.8 (7) | C39—C40—C41 | 104.7 (7) |
C12—C7—N2 | 118.2 (7) | C39—C40—H40 | 127.6 |
C8—C7—N2 | 120.0 (7) | C41—C40—H40 | 127.6 |
C7—C8—C9 | 119.5 (8) | C42—C41—C40 | 107.6 (7) |
C7—C8—H8 | 120.2 | C42—C41—H41 | 126.2 |
C9—C8—H8 | 120.2 | C40—C41—H41 | 126.2 |
C10—C9—C8 | 120.1 (9) | C41—C42—O6 | 110.0 (8) |
C10—C9—H9 | 119.9 | C41—C42—H42 | 125 |
C8—C9—H9 | 119.9 | O6—C42—H42 | 125 |
C9—C10—C11 | 119.3 (8) | C44—C43—C48 | 119.8 (7) |
C9—C10—H10 | 120.3 | C44—C43—N6 | 118.9 (6) |
C11—C10—H10 | 120.3 | C48—C43—N6 | 121.3 (7) |
C12—C11—C10 | 121.0 (8) | C45—C44—C43 | 118.7 (7) |
C12—C11—H11 | 119.5 | C45—C44—H44 | 120.6 |
C10—C11—H11 | 119.5 | C43—C44—H44 | 120.6 |
C7—C12—C11 | 118.2 (8) | C46—C45—C44 | 121.3 (8) |
C7—C12—H12 | 120.9 | C46—C45—H45 | 119.3 |
C11—C12—H12 | 120.9 | C44—C45—H45 | 119.3 |
C18—C13—C14 | 120.7 (7) | C47—C46—C45 | 119.5 (8) |
C18—C13—N2 | 120.1 (7) | C47—C46—H46 | 120.2 |
C14—C13—N2 | 118.8 (7) | C45—C46—H46 | 120.2 |
C15—C14—C13 | 120.4 (8) | C48—C47—C46 | 121.2 (8) |
C15—C14—H14 | 119.8 | C48—C47—H47 | 119.4 |
C13—C14—H14 | 119.8 | C46—C47—H47 | 119.4 |
C14—C15—C16 | 119.2 (8) | C47—C48—C43 | 119.4 (8) |
C14—C15—H15 | 120.4 | C47—C48—H48 | 120.3 |
C16—C15—H15 | 120.4 | C43—C48—H48 | 120.3 |
C17—C16—C15 | 119.7 (8) | C50—C49—C54 | 120.5 (7) |
C17—C16—H16 | 120.1 | C50—C49—N6 | 121.4 (7) |
C15—C16—H16 | 120.1 | C54—C49—N6 | 118.1 (7) |
C16—C17—C18 | 121.2 (8) | C49—C50—C51 | 119.0 (8) |
C16—C17—H17 | 119.4 | C49—C50—H50 | 120.5 |
C18—C17—H17 | 119.4 | C51—C50—H50 | 120.5 |
C13—C18—C17 | 118.7 (7) | C52—C51—C50 | 120.0 (9) |
C13—C18—H18 | 120.6 | C52—C51—H51 | 120 |
C17—C18—H18 | 120.6 | C50—C51—H51 | 120 |
O3—C19—N3 | 129.7 (6) | C51—C52—C53 | 121.9 (9) |
O3—C19—C21 | 117.7 (6) | C51—C52—H52 | 119.1 |
N3—C19—C21 | 112.6 (6) | C53—C52—H52 | 119.1 |
N3—C20—N4 | 113.4 (6) | C52—C53—C54 | 117.5 (10) |
N3—C20—S2 | 129.6 (6) | C52—C53—H53 | 121.2 |
N4—C20—S2 | 116.8 (5) | C54—C53—H53 | 121.2 |
C22—C21—O4 | 110.2 (6) | C49—C54—C53 | 121.1 (9) |
C22—C21—C19 | 131.5 (7) | C49—C54—H54 | 119.5 |
O4—C21—C19 | 118.3 (6) | C53—C54—H54 | 119.5 |
C21—C22—C23 | 106.3 (7) | C1—N1—C2 | 123.2 (6) |
C21—C22—H22 | 126.9 | C2—N2—C13 | 123.4 (6) |
C23—C22—H22 | 126.9 | C2—N2—C7 | 120.3 (5) |
C24—C23—C22 | 106.6 (7) | C13—N2—C7 | 116.2 (5) |
C24—C23—H23 | 126.7 | C20—N3—C19 | 123.9 (6) |
C22—C23—H23 | 126.7 | C20—N4—C31 | 123.1 (6) |
C23—C24—O4 | 111.3 (7) | C20—N4—C25 | 121.3 (5) |
C23—C24—H24 | 124.4 | C31—N4—C25 | 115.6 (6) |
O4—C24—H24 | 124.4 | C38—N5—C37 | 123.1 (6) |
C30—C25—C26 | 120.5 (6) | C38—N6—C43 | 121.9 (6) |
C30—C25—N4 | 121.1 (6) | C38—N6—C49 | 121.9 (6) |
C26—C25—N4 | 118.3 (7) | C43—N6—C49 | 116.0 (6) |
C27—C26—C25 | 117.8 (7) | C1—O1—Co1 | 126.7 (4) |
C27—C26—H26 | 121.1 | C3—O2—C6 | 105.2 (6) |
C25—C26—H26 | 121.1 | C19—O3—Co1 | 127.0 (4) |
C28—C27—C26 | 121.7 (7) | C24—O4—C21 | 105.7 (6) |
C28—C27—H27 | 119.2 | C37—O5—Co1 | 127.7 (4) |
C26—C27—H27 | 119.2 | C39—O6—C42 | 106.3 (6) |
C29—C28—C27 | 119.1 (7) | C2—S1—Co1 | 104.5 (2) |
C29—C28—H28 | 120.4 | C20—S2—Co1 | 106.4 (2) |
C27—C28—H28 | 120.4 | C38—S3—Co1 | 106.0 (3) |
C28—C29—C30 | 120.8 (7) | O5—Co1—O3 | 88.20 (19) |
C28—C29—H29 | 119.6 | O5—Co1—O1 | 85.77 (19) |
C30—C29—H29 | 119.6 | O3—Co1—O1 | 85.5 (2) |
C25—C30—C29 | 120.2 (7) | O5—Co1—S3 | 93.19 (15) |
C25—C30—H30 | 119.9 | O3—Co1—S3 | 176.11 (15) |
C29—C30—H30 | 119.9 | O1—Co1—S3 | 90.95 (15) |
C36—C31—C32 | 119.5 (6) | O5—Co1—S2 | 91.05 (15) |
C36—C31—N4 | 121.9 (6) | O3—Co1—S2 | 93.98 (15) |
C32—C31—N4 | 118.4 (6) | O1—Co1—S2 | 176.80 (14) |
C33—C32—C31 | 120.0 (7) | S3—Co1—S2 | 89.62 (8) |
C33—C32—H32 | 120 | O5—Co1—S1 | 178.62 (16) |
C31—C32—H32 | 120 | O3—Co1—S1 | 90.58 (13) |
C32—C33—C34 | 120.7 (7) | O1—Co1—S1 | 93.51 (14) |
C32—C33—H33 | 119.6 | S3—Co1—S1 | 87.99 (7) |
C34—C33—H33 | 119.6 | S2—Co1—S1 | 89.66 (7) |
O1—C1—C3—C4 | −179.4 (8) | C14—C13—N2—C7 | −70.9 (8) |
N1—C1—C3—C4 | 1.9 (12) | C12—C7—N2—C2 | 105.8 (8) |
O1—C1—C3—O2 | 3.8 (10) | C8—C7—N2—C2 | −76.9 (9) |
N1—C1—C3—O2 | −174.9 (6) | C12—C7—N2—C13 | −71.2 (8) |
O2—C3—C4—C5 | −0.3 (10) | C8—C7—N2—C13 | 106.1 (8) |
C1—C3—C4—C5 | −177.3 (8) | N4—C20—N3—C19 | −169.6 (6) |
C3—C4—C5—C6 | 0.6 (11) | S2—C20—N3—C19 | 14.7 (10) |
C4—C5—C6—O2 | −0.6 (11) | O3—C19—N3—C20 | −4.5 (11) |
C12—C7—C8—C9 | 1.0 (11) | C21—C19—N3—C20 | 175.4 (6) |
N2—C7—C8—C9 | −176.2 (6) | N3—C20—N4—C31 | 172.6 (6) |
C7—C8—C9—C10 | −0.1 (12) | S2—C20—N4—C31 | −11.1 (9) |
C8—C9—C10—C11 | −0.6 (12) | N3—C20—N4—C25 | −7.0 (9) |
C9—C10—C11—C12 | 0.5 (12) | S2—C20—N4—C25 | 169.3 (5) |
C8—C7—C12—C11 | −1.1 (11) | C36—C31—N4—C20 | −63.5 (10) |
N2—C7—C12—C11 | 176.2 (6) | C32—C31—N4—C20 | 121.4 (7) |
C10—C11—C12—C7 | 0.3 (12) | C36—C31—N4—C25 | 116.1 (7) |
C18—C13—C14—C15 | 1.4 (11) | C32—C31—N4—C25 | −59.0 (9) |
N2—C13—C14—C15 | 173.9 (6) | C30—C25—N4—C20 | 121.4 (8) |
C13—C14—C15—C16 | −1.8 (11) | C26—C25—N4—C20 | −63.8 (9) |
C14—C15—C16—C17 | 1.2 (11) | C30—C25—N4—C31 | −58.2 (9) |
C15—C16—C17—C18 | −0.3 (11) | C26—C25—N4—C31 | 116.6 (7) |
C14—C13—C18—C17 | −0.5 (11) | N6—C38—N5—C37 | −173.5 (6) |
N2—C13—C18—C17 | −172.9 (6) | S3—C38—N5—C37 | 3.9 (11) |
C16—C17—C18—C13 | −0.1 (11) | O5—C37—N5—C38 | −12.4 (12) |
O3—C19—C21—C22 | 178.2 (8) | C39—C37—N5—C38 | 165.3 (6) |
N3—C19—C21—C22 | −1.8 (11) | N5—C38—N6—C43 | −176.6 (6) |
O3—C19—C21—O4 | −2.7 (9) | S3—C38—N6—C43 | 5.7 (9) |
N3—C19—C21—O4 | 177.4 (6) | N5—C38—N6—C49 | 8.5 (10) |
O4—C21—C22—C23 | 0.3 (9) | S3—C38—N6—C49 | −169.2 (5) |
C19—C21—C22—C23 | 179.5 (7) | C44—C43—N6—C38 | −117.6 (8) |
C21—C22—C23—C24 | 0.6 (9) | C48—C43—N6—C38 | 64.3 (10) |
C22—C23—C24—O4 | −1.2 (10) | C44—C43—N6—C49 | 57.6 (9) |
C30—C25—C26—C27 | 0.2 (11) | C48—C43—N6—C49 | −120.5 (8) |
N4—C25—C26—C27 | −174.6 (7) | C50—C49—N6—C38 | 57.1 (10) |
C25—C26—C27—C28 | 0.1 (12) | C54—C49—N6—C38 | −125.7 (8) |
C26—C27—C28—C29 | 0.4 (12) | C50—C49—N6—C43 | −118.1 (8) |
C27—C28—C29—C30 | −1.1 (12) | C54—C49—N6—C43 | 59.1 (9) |
C26—C25—C30—C29 | −1.0 (11) | N1—C1—O1—Co1 | 14.3 (11) |
N4—C25—C30—C29 | 173.7 (6) | C3—C1—O1—Co1 | −164.0 (5) |
C28—C29—C30—C25 | 1.4 (11) | C4—C3—O2—C6 | −0.1 (9) |
C36—C31—C32—C33 | −1.1 (11) | C1—C3—O2—C6 | 177.4 (7) |
N4—C31—C32—C33 | 174.2 (7) | C5—C6—O2—C3 | 0.5 (10) |
C31—C32—C33—C34 | 1.8 (12) | N3—C19—O3—Co1 | −26.9 (10) |
C32—C33—C34—C35 | −0.7 (12) | C21—C19—O3—Co1 | 153.2 (5) |
C33—C34—C35—C36 | −1.1 (12) | C23—C24—O4—C21 | 1.4 (9) |
C34—C35—C36—C31 | 1.8 (12) | C22—C21—O4—C24 | −1.0 (8) |
C32—C31—C36—C35 | −0.7 (11) | C19—C21—O4—C24 | 179.6 (6) |
N4—C31—C36—C35 | −175.8 (7) | N5—C37—O5—Co1 | −11.8 (11) |
O5—C37—C39—C40 | 178.2 (7) | C39—C37—O5—Co1 | 170.6 (4) |
N5—C37—C39—C40 | 0.1 (11) | C40—C39—O6—C42 | 0.4 (8) |
O5—C37—C39—O6 | −1.3 (9) | C37—C39—O6—C42 | 179.9 (6) |
N5—C37—C39—O6 | −179.3 (6) | C41—C42—O6—C39 | 0.2 (9) |
O6—C39—C40—C41 | −0.7 (9) | N1—C2—S1—Co1 | −22.5 (8) |
C37—C39—C40—C41 | 179.8 (7) | N2—C2—S1—Co1 | 158.8 (5) |
C39—C40—C41—C42 | 0.8 (9) | N3—C20—S2—Co1 | 2.9 (7) |
C40—C41—C42—O6 | −0.6 (10) | N4—C20—S2—Co1 | −172.7 (4) |
C48—C43—C44—C45 | −0.8 (11) | N5—C38—S3—Co1 | 19.4 (7) |
N6—C43—C44—C45 | −178.9 (7) | N6—C38—S3—Co1 | −163.3 (5) |
C43—C44—C45—C46 | −0.6 (12) | C37—O5—Co1—O3 | −153.8 (6) |
C44—C45—C46—C47 | 1.1 (14) | C37—O5—Co1—O1 | 120.6 (6) |
C45—C46—C47—C48 | −0.2 (15) | C37—O5—Co1—S3 | 29.9 (5) |
C46—C47—C48—C43 | −1.2 (14) | C37—O5—Co1—S2 | −59.8 (5) |
C44—C43—C48—C47 | 1.7 (13) | C19—O3—Co1—O5 | 125.6 (5) |
N6—C43—C48—C47 | 179.8 (7) | C19—O3—Co1—O1 | −148.5 (5) |
C54—C49—C50—C51 | −1.5 (12) | C19—O3—Co1—S2 | 34.7 (5) |
N6—C49—C50—C51 | 175.6 (7) | C19—O3—Co1—S1 | −55.0 (5) |
C49—C50—C51—C52 | 0.7 (13) | C1—O1—Co1—O5 | 147.3 (6) |
C50—C51—C52—C53 | 0.9 (15) | C1—O1—Co1—O3 | 58.8 (6) |
C51—C52—C53—C54 | −1.6 (15) | C1—O1—Co1—S3 | −119.6 (5) |
C50—C49—C54—C53 | 0.7 (13) | C1—O1—Co1—S1 | −31.6 (6) |
N6—C49—C54—C53 | −176.5 (8) | C38—S3—Co1—O5 | −27.9 (3) |
C52—C53—C54—C49 | 0.8 (14) | C38—S3—Co1—O1 | −113.7 (3) |
O1—C1—N1—C2 | 8.9 (12) | C38—S3—Co1—S2 | 63.1 (3) |
C3—C1—N1—C2 | −172.6 (6) | C38—S3—Co1—S1 | 152.8 (3) |
N2—C2—N1—C1 | 178.9 (6) | C20—S2—Co1—O5 | −108.4 (3) |
S1—C2—N1—C1 | 0.1 (11) | C20—S2—Co1—O3 | −20.2 (3) |
N1—C2—N2—C13 | 169.1 (6) | C20—S2—Co1—S3 | 158.4 (2) |
S1—C2—N2—C13 | −11.9 (9) | C20—S2—Co1—S1 | 70.4 (2) |
N1—C2—N2—C7 | −7.6 (10) | C2—S1—Co1—O3 | −56.2 (3) |
S1—C2—N2—C7 | 171.3 (5) | C2—S1—Co1—O1 | 29.4 (3) |
C18—C13—N2—C2 | −75.3 (9) | C2—S1—Co1—S3 | 120.2 (3) |
C14—C13—N2—C2 | 112.2 (8) | C2—S1—Co1—S2 | −150.2 (3) |
C18—C13—N2—C7 | 101.6 (8) |
Experimental details
Crystal data | |
Chemical formula | [Co(C18H13N2O2S)3] |
Mr | 1023.05 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 150 |
a, b, c (Å) | 10.0236 (11), 13.1438 (16), 19.388 (3) |
α, β, γ (°) | 79.357 (7), 83.477 (8), 71.152 (8) |
V (Å3) | 2371.8 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.55 |
Crystal size (mm) | 0.15 × 0.13 × 0.02 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Gaussian (Coppens et al., 1965) |
Tmin, Tmax | 0.955, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13609, 8289, 4680 |
Rint | 0.092 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.086, 0.222, 1.19 |
No. of reflections | 8289 |
No. of parameters | 632 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.51, −0.53 |
Computer programs: COLLECT (Nonius, 1998), DENZO/SCALEPACK (Otwinowski & Minor, 1997), DENZO/SCALEPACK, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).
O1—Co1 | 1.939 (5) | S1—Co1 | 2.217 (2) |
O3—Co1 | 1.920 (5) | S2—Co1 | 2.214 (2) |
O5—Co1 | 1.919 (4) | S3—Co1 | 2.196 (2) |
O5—Co1—O3 | 88.20 (19) | O1—Co1—S2 | 176.80 (14) |
O5—Co1—O1 | 85.77 (19) | S3—Co1—S2 | 89.62 (8) |
O3—Co1—O1 | 85.5 (2) | O5—Co1—S1 | 178.62 (16) |
O5—Co1—S3 | 93.19 (15) | O3—Co1—S1 | 90.58 (13) |
O3—Co1—S3 | 176.11 (15) | O1—Co1—S1 | 93.51 (14) |
O1—Co1—S3 | 90.95 (15) | S3—Co1—S1 | 87.99 (7) |
O5—Co1—S2 | 91.05 (15) | S2—Co1—S1 | 89.66 (7) |
O3—Co1—S2 | 93.98 (15) |
Acknowledgements
The authors thank the Crystallography Group, São Carlos Physics Institute, USP, Brazil, for allowing the X-ray data collection. The authors acknowledge financial support from Brazilian agencies CAPES (Project 018/05) and CNPq (Project 134576/2007–1).
References
Arslan, H., Flörke, U. & Külcü, N. (2003). Transition Met. Chem. 28, 816–819. Web of Science CSD CrossRef CAS Google Scholar
Coppens, P., Leiserowitz, L. & Rabinovich, D. (1965). Acta Cryst. 18, 1035–1038. CrossRef CAS IUCr Journals Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Hernández, W., Spodine, E., Muñoz, J. C., Beyer, L., Schröder, U., Ferreira, J. & Pavani, M. (2003). Bioinorg. Chem. Appl. 1, 271–284. Google Scholar
Jia, D.-X., Zhu, A.-M., Deng, J. & Zhang, Y. (2007). Z. Anorg. Allg. Chem. 633, 2059–2063. Web of Science CSD CrossRef CAS Google Scholar
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Pérez, H., Mascarenhas, Y., Plutín, A. M., de Souza Corrêa, R. & Duque, J. (2008). Acta Cryst. E64, m503. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Substituted N-acylthioureas are well known as chelating agents. Over recent years, many transition metal complexes with thiourea derivatives have been reported (Arslan et al., 2003), because this kind of ligands display a remarkably rich coordination chemistry.
In this paper, we report the crystal structure of the title compound (Fig. 1), which presents an octahedral environment about the CoIII atom with the ligands coordinating in a relatively distorted manner (Table 1). The Co—S bond lengths lie within the range of those found in the related structure (Jia et al., 2007; Pérez et al., 2008). The lengths of C—O, C—S and C—N bonds in the chelate rings are between characteristic single and double bond lengths; they are shorter than single bond and longer than double bond. These results can be explained by the existence of delocalization in the chelate rings. Fig. 2 shows the arrangement of the complex molecules in the unit cell.