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The structures of the title triethanolamine (tea) complexes of CdII and HgII saccharinates, bis(triethanolamine)-κ3O,N,O′;κ4O,N,O′,O′′-cadmium(II) 1,2-benzisothiazol-3(2H)-onate 1,1-dioxide, [Cd(C6H15NO3)2](C7H4NO3S)2, (I), and bis(triethanolamine)-κ3O,N,O′;κ4O,N,O′,O′′-mercury(II) 1,2-benzisothiazol-3(2H)-onate 1,1-dioxide, [Hg(C6H15NO3)2](C7H4NO3S)2, (II), or [M(tea)2](sac)2, where M is CdII or HgII and sac is the saccharinate anion, reveal seven-coordinate metal ions in both complexes. Both complex cations, [M(tea)2]2+, adopt a monocapped trigonal prism geometry in which the two tea ligands exhibit different coordination modes to achieve seven-coordination. One tea ligand acts as a tetradentate ligand using all its donor atoms, while the other behaves as a tridentate O,N,O′-donor ligand, with one of its ethanol groups remaining uncoordinated. The H atoms of the free and coordinated hydroxyl groups of the tea ligands are involved in hydrogen bonding with the amine N atom, and with the carbonyl and sulfonyl O atoms of neighbouring sac ions, forming an infinite three-dimensional network. A weak π–π interaction between the phenyl rings of the sac ions also occurs.
Supporting information
CCDC references: 162852; 162853
The preparation and spectral characterization of tea complexes of first-row
divalent transition metal saccharinates, including the present CdII and
HgII saccharinates, have been reported elsewhere by Topcu et al.
(2001b). The polycrystalline solid complexes, (I) and (II), were
crystallized from solutions in methanol-2-propanol (1:1, v/v) at
room temperature to obtain suitable single crystals for X-ray analysis.
Hydroxyl H atoms were located from the difference map for (II) and were
geometrically positioned for (I). All hydroxyl H atoms were refined with a
rotating model, with Uiso 1.5 times that of O atoms, while the other
H atoms were placed in calculated positions and refined with a riding model,
with Uiso 1.2 times that of their attached atoms.
For both compounds, data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2000); software used to prepare material for publication: SHELXL97.
(I) bis(triethanolamine)-
κ3O,
N,
O';
κ4O,
N,
O',
O''-cadmium(II) 1,2-bensisothiazol-3(2
H)-onate
1,1-dioxide
top
Crystal data top
[Cd(C6H15NO3)2]2C7H4NO3S | Z = 2 |
Mr = 775.12 | F(000) = 796 |
Triclinic, P1 | Dx = 1.664 Mg m−3 |
a = 13.2825 (9) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 14.9093 (11) Å | Cell parameters from 24 reflections |
c = 8.9376 (10) Å | θ = 10.5–13.2° |
α = 98.002 (8)° | µ = 0.91 mm−1 |
β = 102.662 (8)° | T = 293 K |
γ = 63.762 (5)° | Prism, colourless |
V = 1547.2 (2) Å3 | 0.4 × 0.2 × 0.2 mm |
Data collection top
Rigaku AFC-7S diffractometer | 7948 reflections with I > 2σ(I) |
Radiation source: X-ray tube | Rint = 0.025 |
Graphite monochromator | θmax = 32.5°, θmin = 2.3° |
ω/2θ scans | h = 0→20 |
Absorption correction: ψ-scan (North et al., 1968) | k = −20→22 |
Tmin = 0.797, Tmax = 0.834 | l = −13→13 |
12760 measured reflections | 3 standard reflections every 150 reflections |
11203 independent reflections | intensity decay: 7.7% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.047P)2 + 0.051P] where P = (Fo2 + 2Fc2)/3 |
11203 reflections | (Δ/σ)max = 0.001 |
478 parameters | Δρmax = 0.80 e Å−3 |
145 restraints | Δρmin = −0.87 e Å−3 |
Crystal data top
[Cd(C6H15NO3)2]2C7H4NO3S | γ = 63.762 (5)° |
Mr = 775.12 | V = 1547.2 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 13.2825 (9) Å | Mo Kα radiation |
b = 14.9093 (11) Å | µ = 0.91 mm−1 |
c = 8.9376 (10) Å | T = 293 K |
α = 98.002 (8)° | 0.4 × 0.2 × 0.2 mm |
β = 102.662 (8)° | |
Data collection top
Rigaku AFC-7S diffractometer | 7948 reflections with I > 2σ(I) |
Absorption correction: ψ-scan (North et al., 1968) | Rint = 0.025 |
Tmin = 0.797, Tmax = 0.834 | 3 standard reflections every 150 reflections |
12760 measured reflections | intensity decay: 7.7% |
11203 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.039 | 145 restraints |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.80 e Å−3 |
11203 reflections | Δρmin = −0.87 e Å−3 |
478 parameters | |
Special details top
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cd1 | −0.01644 (1) | 0.28894 (1) | 0.27090 (2) | 0.0272 (1) | |
N2 | 0.10586 (17) | 0.21213 (15) | 0.0873 (2) | 0.0296 (4) | |
O1 | −0.05711 (18) | 0.43643 (14) | 0.4318 (2) | 0.0408 (4) | |
H1 | −0.0966 | 0.4950 | 0.3964 | 0.061* | |
O2 | −0.18230 (17) | 0.29080 (18) | 0.0987 (2) | 0.0507 (5) | |
H2 | −0.1895 | 0.2449 | 0.0339 | 0.076* | |
O3 | 0.03391 (19) | 0.12113 (15) | 0.3383 (3) | 0.0518 (5) | |
H3 | 0.0943 | 0.0667 | 0.3330 | 0.078* | |
O4 | 0.16688 (17) | 0.24907 (16) | 0.4093 (2) | 0.0447 (5) | |
H4 | 0.1799 | 0.2873 | 0.4847 | 0.067* | |
O5 | −0.04377 (17) | 0.41711 (14) | 0.1195 (2) | 0.0395 (4) | |
H5 | −0.1120 | 0.4637 | 0.1081 | 0.059* | |
N1 | −0.14402 (18) | 0.29567 (15) | 0.4284 (2) | 0.0370 (5) | |
C1A | −0.1232 (11) | 0.3535 (6) | 0.5727 (7) | 0.052 (2) | 0.307 (5) |
H1A1 | −0.0488 | 0.3142 | 0.6313 | 0.062* | 0.307 (5) |
H1A2 | −0.1801 | 0.3661 | 0.6345 | 0.062* | 0.307 (5) |
C2A | −0.1283 (10) | 0.4520 (6) | 0.5382 (11) | 0.047 (3) | 0.307 (5) |
H2A1 | −0.2063 | 0.4962 | 0.4965 | 0.057* | 0.307 (5) |
H2A2 | −0.1041 | 0.4837 | 0.6324 | 0.057* | 0.307 (5) |
C3A | −0.2617 (5) | 0.3342 (11) | 0.3411 (9) | 0.063 (3) | 0.307 (5) |
H3A1 | −0.2931 | 0.4065 | 0.3401 | 0.076* | 0.307 (5) |
H3A2 | −0.3083 | 0.3176 | 0.3920 | 0.076* | 0.307 (5) |
C4A | −0.2667 (6) | 0.2911 (10) | 0.1780 (7) | 0.068 (3) | 0.307 (5) |
H4A1 | −0.2571 | 0.2228 | 0.1787 | 0.081* | 0.307 (5) |
H4A2 | −0.3419 | 0.3291 | 0.1202 | 0.081* | 0.307 (5) |
C5A | −0.1048 (7) | 0.1969 (6) | 0.4934 (17) | 0.051 (3) | 0.307 (5) |
H5A1 | −0.1504 | 0.1636 | 0.4350 | 0.061* | 0.307 (5) |
H5A2 | −0.1181 | 0.2077 | 0.5982 | 0.061* | 0.307 (5) |
C6A | 0.0181 (8) | 0.1298 (6) | 0.4927 (7) | 0.049 (2) | 0.307 (5) |
H6A1 | 0.0659 | 0.1583 | 0.5593 | 0.059* | 0.307 (5) |
H6A2 | 0.0374 | 0.0646 | 0.5283 | 0.059* | 0.307 (5) |
C1B | −0.1880 (4) | 0.3945 (3) | 0.5109 (5) | 0.0466 (10) | 0.693 (5) |
H1B1 | −0.2165 | 0.3897 | 0.5990 | 0.056* | 0.693 (5) |
H1B2 | −0.2509 | 0.4423 | 0.4436 | 0.056* | 0.693 (5) |
C2B | −0.0957 (5) | 0.4314 (4) | 0.5641 (5) | 0.0465 (14) | 0.693 (5) |
H2B1 | −0.1261 | 0.4969 | 0.6161 | 0.056* | 0.693 (5) |
H2B2 | −0.0334 | 0.3856 | 0.6347 | 0.056* | 0.693 (5) |
C3B | −0.2414 (4) | 0.2823 (4) | 0.3237 (5) | 0.0478 (11) | 0.693 (5) |
H3B1 | −0.3057 | 0.3071 | 0.3767 | 0.057* | 0.693 (5) |
H3B2 | −0.2195 | 0.2114 | 0.2990 | 0.057* | 0.693 (5) |
C4B | −0.2778 (3) | 0.3357 (4) | 0.1773 (5) | 0.0463 (11) | 0.693 (5) |
H4B1 | −0.3434 | 0.3280 | 0.1149 | 0.056* | 0.693 (5) |
H4B2 | −0.2979 | 0.4065 | 0.1992 | 0.056* | 0.693 (5) |
C5B | −0.0789 (5) | 0.2120 (3) | 0.5316 (5) | 0.0464 (13) | 0.693 (5) |
H5B1 | −0.1301 | 0.2075 | 0.5897 | 0.056* | 0.693 (5) |
H5B2 | −0.0211 | 0.2262 | 0.6041 | 0.056* | 0.693 (5) |
C6B | −0.0225 (4) | 0.1135 (3) | 0.4496 (6) | 0.0478 (11) | 0.693 (5) |
H6B1 | 0.0322 | 0.0651 | 0.5233 | 0.057* | 0.693 (5) |
H6B2 | −0.0794 | 0.0896 | 0.3999 | 0.057* | 0.693 (5) |
C12 | 0.1431 (3) | 0.0592 (3) | −0.1009 (4) | 0.0545 (8) | |
H12A | 0.1981 | 0.0076 | −0.0321 | 0.065* | |
H12B | 0.1001 | 0.0297 | −0.1760 | 0.065* | |
O6A | 0.2021 (15) | 0.0933 (12) | −0.1778 (17) | 0.064 (2) | 0.56 (3) |
H6A | 0.2475 | 0.0422 | −0.2290 | 0.096* | 0.56 (3) |
O6B | 0.1648 (17) | 0.1042 (14) | −0.2136 (17) | 0.065 (2) | 0.44 (3) |
H6B | 0.1936 | 0.0573 | −0.2843 | 0.097* | 0.44 (3) |
C7 | 0.2218 (2) | 0.1573 (2) | 0.1758 (3) | 0.0366 (5) | |
H7A | 0.2771 | 0.1387 | 0.1090 | 0.044* | |
H7B | 0.2270 | 0.0962 | 0.2100 | 0.044* | |
C8 | 0.2516 (2) | 0.2183 (2) | 0.3149 (3) | 0.0416 (6) | |
H8A | 0.3261 | 0.1781 | 0.3725 | 0.050* | |
H8B | 0.2540 | 0.2765 | 0.2818 | 0.050* | |
C9 | 0.1017 (2) | 0.2912 (2) | −0.0018 (3) | 0.0376 (5) | |
H9A | 0.1237 | 0.2623 | −0.1003 | 0.045* | |
H9B | 0.1560 | 0.3167 | 0.0531 | 0.045* | |
C10 | −0.0161 (3) | 0.3764 (2) | −0.0275 (3) | 0.0406 (6) | |
H10A | −0.0170 | 0.4272 | −0.0856 | 0.049* | |
H10B | −0.0710 | 0.3522 | −0.0844 | 0.049* | |
C11 | 0.0631 (2) | 0.1427 (2) | −0.0107 (3) | 0.0394 (6) | |
H11A | −0.0035 | 0.1824 | −0.0827 | 0.047* | |
H11B | 0.0377 | 0.1131 | 0.0548 | 0.047* | |
S2 | −0.35369 (6) | 0.60541 (5) | −0.03679 (7) | 0.03579 (14) | |
N4 | −0.2564 (2) | 0.56690 (16) | 0.1148 (3) | 0.0388 (5) | |
O10 | −0.1960 (2) | 0.62917 (15) | 0.3460 (2) | 0.0519 (6) | |
O11 | −0.3020 (2) | 0.59600 (18) | −0.1672 (2) | 0.0526 (6) | |
O12 | −0.4318 (2) | 0.56060 (18) | −0.0570 (3) | 0.0569 (6) | |
C20 | −0.2628 (2) | 0.64105 (19) | 0.2207 (3) | 0.0355 (5) | |
C21 | −0.3575 (2) | 0.73971 (18) | 0.1733 (3) | 0.0321 (5) | |
C22 | −0.3885 (3) | 0.8320 (2) | 0.2535 (3) | 0.0422 (6) | |
H22 | −0.3488 | 0.8384 | 0.3509 | 0.051* | |
C23 | −0.4800 (3) | 0.9141 (2) | 0.1849 (4) | 0.0499 (7) | |
H23 | −0.5025 | 0.9764 | 0.2371 | 0.060* | |
C24 | −0.5384 (3) | 0.9044 (2) | 0.0392 (4) | 0.0499 (7) | |
H24 | −0.5990 | 0.9607 | −0.0052 | 0.060* | |
C25 | −0.5087 (2) | 0.8129 (2) | −0.0417 (3) | 0.0441 (6) | |
H25 | −0.5483 | 0.8063 | −0.1391 | 0.053* | |
C26 | −0.4171 (2) | 0.73126 (19) | 0.0295 (3) | 0.0337 (5) | |
S1 | 0.32615 (6) | −0.08103 (5) | −0.51871 (8) | 0.03649 (14) | |
O7 | 0.18760 (19) | −0.14470 (16) | −0.8900 (3) | 0.0540 (6) | |
O8 | 0.3911 (2) | −0.02466 (19) | −0.5098 (3) | 0.0590 (6) | |
O9 | 0.2768 (2) | −0.06974 (17) | −0.3842 (2) | 0.0521 (6) | |
N3 | 0.2298 (2) | −0.05921 (17) | −0.6727 (3) | 0.0419 (5) | |
C13 | 0.2481 (2) | −0.14247 (19) | −0.7642 (3) | 0.0356 (5) | |
C14 | 0.3498 (2) | −0.23353 (19) | −0.6988 (3) | 0.0329 (5) | |
C15 | 0.3886 (3) | −0.3315 (2) | −0.7561 (3) | 0.0452 (7) | |
H15 | 0.3530 | −0.3489 | −0.8497 | 0.054* | |
C16 | 0.4830 (3) | −0.4039 (2) | −0.6687 (4) | 0.0575 (9) | |
H16 | 0.5112 | −0.4703 | −0.7054 | 0.069* | |
C17 | 0.5356 (3) | −0.3784 (3) | −0.5283 (4) | 0.0552 (9) | |
H17 | 0.5975 | −0.4280 | −0.4715 | 0.066* | |
C18 | 0.4970 (2) | −0.2802 (2) | −0.4720 (3) | 0.0442 (7) | |
H18 | 0.5322 | −0.2624 | −0.3784 | 0.053* | |
C19 | 0.4041 (2) | −0.20944 (19) | −0.5600 (3) | 0.0331 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cd1 | 0.02796 (8) | 0.02723 (8) | 0.02494 (8) | −0.01058 (6) | 0.00641 (6) | −0.00203 (5) |
N2 | 0.0306 (10) | 0.0295 (9) | 0.0272 (9) | −0.0123 (8) | 0.0071 (8) | −0.0054 (7) |
O1 | 0.0562 (12) | 0.0298 (9) | 0.0352 (9) | −0.0172 (9) | 0.0116 (9) | −0.0035 (7) |
O2 | 0.0351 (10) | 0.0607 (14) | 0.0467 (11) | −0.0200 (10) | 0.0015 (9) | −0.0175 (10) |
O3 | 0.0495 (12) | 0.0313 (10) | 0.0668 (14) | −0.0036 (9) | 0.0213 (11) | 0.0081 (10) |
O4 | 0.0349 (10) | 0.0490 (11) | 0.0374 (10) | −0.0143 (9) | −0.0011 (8) | −0.0128 (8) |
O5 | 0.0436 (11) | 0.0313 (9) | 0.0313 (9) | −0.0028 (8) | 0.0111 (8) | 0.0022 (7) |
N1 | 0.0376 (11) | 0.0343 (11) | 0.0400 (11) | −0.0126 (9) | 0.0156 (9) | −0.0002 (9) |
C1A | 0.067 (5) | 0.050 (4) | 0.035 (4) | −0.020 (4) | 0.015 (4) | 0.001 (3) |
C2A | 0.061 (5) | 0.049 (4) | 0.025 (4) | −0.020 (4) | 0.009 (4) | −0.005 (3) |
C3A | 0.035 (4) | 0.069 (5) | 0.064 (4) | 0.002 (4) | 0.014 (4) | 0.008 (5) |
C4A | 0.029 (4) | 0.064 (5) | 0.082 (5) | −0.006 (4) | 0.007 (4) | −0.030 (5) |
C5A | 0.051 (4) | 0.056 (5) | 0.047 (5) | −0.020 (4) | 0.009 (4) | 0.015 (4) |
C6A | 0.058 (4) | 0.038 (4) | 0.053 (5) | −0.017 (3) | 0.011 (4) | 0.012 (4) |
C1B | 0.052 (2) | 0.041 (2) | 0.045 (2) | −0.0114 (18) | 0.0269 (19) | −0.0029 (17) |
C2B | 0.066 (3) | 0.044 (2) | 0.0250 (19) | −0.021 (2) | 0.008 (2) | −0.0050 (17) |
C3B | 0.030 (2) | 0.042 (2) | 0.071 (3) | −0.0108 (18) | 0.0112 (19) | 0.012 (2) |
C4B | 0.0275 (19) | 0.046 (3) | 0.056 (2) | −0.0095 (18) | 0.0069 (17) | −0.0064 (19) |
C5B | 0.052 (3) | 0.049 (2) | 0.037 (2) | −0.0154 (19) | 0.012 (2) | 0.0144 (18) |
C6B | 0.051 (3) | 0.0333 (19) | 0.064 (3) | −0.0185 (17) | 0.010 (2) | 0.0153 (18) |
C12 | 0.066 (2) | 0.0463 (17) | 0.0530 (18) | −0.0263 (16) | 0.0243 (16) | −0.0228 (14) |
O6A | 0.071 (7) | 0.067 (3) | 0.063 (5) | −0.034 (5) | 0.042 (4) | −0.033 (3) |
O6B | 0.072 (7) | 0.068 (3) | 0.063 (5) | −0.034 (5) | 0.042 (4) | −0.034 (3) |
C7 | 0.0278 (11) | 0.0357 (12) | 0.0402 (13) | −0.0093 (10) | 0.0067 (10) | −0.0036 (10) |
C8 | 0.0342 (13) | 0.0493 (16) | 0.0412 (14) | −0.0210 (12) | 0.0012 (11) | −0.0008 (12) |
C9 | 0.0428 (14) | 0.0402 (14) | 0.0327 (12) | −0.0174 (12) | 0.0160 (11) | −0.0031 (10) |
C10 | 0.0497 (16) | 0.0385 (13) | 0.0263 (11) | −0.0119 (12) | 0.0073 (11) | 0.0022 (10) |
C11 | 0.0400 (14) | 0.0417 (14) | 0.0358 (13) | −0.0197 (12) | 0.0088 (11) | −0.0113 (11) |
S2 | 0.0356 (3) | 0.0335 (3) | 0.0322 (3) | −0.0135 (3) | 0.0004 (2) | −0.0046 (2) |
N4 | 0.0386 (12) | 0.0279 (10) | 0.0351 (11) | −0.0064 (9) | −0.0018 (9) | −0.0045 (8) |
O10 | 0.0549 (13) | 0.0358 (10) | 0.0389 (10) | −0.0078 (9) | −0.0147 (9) | −0.0028 (8) |
O11 | 0.0587 (14) | 0.0578 (14) | 0.0346 (10) | −0.0199 (11) | 0.0125 (10) | −0.0084 (9) |
O12 | 0.0558 (14) | 0.0520 (13) | 0.0654 (15) | −0.0337 (11) | −0.0008 (12) | −0.0087 (11) |
C20 | 0.0389 (13) | 0.0282 (11) | 0.0319 (12) | −0.0108 (10) | 0.0004 (10) | −0.0004 (9) |
C21 | 0.0332 (12) | 0.0264 (10) | 0.0305 (11) | −0.0087 (9) | 0.0031 (9) | 0.0001 (9) |
C22 | 0.0485 (16) | 0.0309 (12) | 0.0363 (13) | −0.0108 (11) | 0.0045 (12) | −0.0062 (10) |
C23 | 0.0561 (19) | 0.0298 (13) | 0.0508 (17) | −0.0079 (13) | 0.0098 (14) | −0.0034 (12) |
C24 | 0.0416 (16) | 0.0368 (14) | 0.0548 (18) | −0.0030 (12) | 0.0044 (13) | 0.0054 (13) |
C25 | 0.0373 (14) | 0.0409 (14) | 0.0403 (14) | −0.0078 (12) | −0.0021 (11) | 0.0040 (12) |
C26 | 0.0311 (12) | 0.0306 (11) | 0.0342 (12) | −0.0103 (10) | 0.0022 (9) | 0.0004 (9) |
S1 | 0.0423 (3) | 0.0332 (3) | 0.0365 (3) | −0.0194 (3) | 0.0124 (3) | −0.0107 (2) |
O7 | 0.0513 (13) | 0.0421 (11) | 0.0491 (12) | −0.0142 (10) | −0.0139 (10) | −0.0022 (9) |
O8 | 0.0770 (17) | 0.0593 (14) | 0.0603 (14) | −0.0504 (14) | 0.0167 (13) | −0.0176 (11) |
O9 | 0.0628 (14) | 0.0478 (12) | 0.0454 (12) | −0.0199 (11) | 0.0277 (11) | −0.0145 (9) |
N3 | 0.0421 (13) | 0.0268 (10) | 0.0479 (13) | −0.0104 (9) | 0.0037 (10) | −0.0043 (9) |
C13 | 0.0351 (13) | 0.0301 (11) | 0.0379 (13) | −0.0133 (10) | 0.0031 (10) | −0.0023 (10) |
C14 | 0.0312 (12) | 0.0293 (11) | 0.0329 (11) | −0.0103 (9) | 0.0049 (9) | −0.0047 (9) |
C15 | 0.0465 (16) | 0.0351 (13) | 0.0381 (14) | −0.0096 (12) | 0.0024 (12) | −0.0122 (11) |
C16 | 0.060 (2) | 0.0326 (14) | 0.0543 (18) | −0.0019 (14) | 0.0061 (16) | −0.0091 (13) |
C17 | 0.0403 (16) | 0.0474 (17) | 0.0489 (17) | 0.0051 (13) | 0.0027 (13) | 0.0026 (14) |
C18 | 0.0325 (13) | 0.0528 (17) | 0.0370 (14) | −0.0128 (12) | 0.0039 (11) | −0.0077 (12) |
C19 | 0.0300 (11) | 0.0348 (12) | 0.0330 (12) | −0.0136 (10) | 0.0081 (9) | −0.0064 (9) |
Geometric parameters (Å, º) top
Cd1—O4 | 2.3274 (19) | C6B—H6B1 | 0.9700 |
Cd1—O5 | 2.3464 (19) | C6B—H6B2 | 0.9700 |
Cd1—O1 | 2.3676 (19) | C12—O6A | 1.426 (5) |
Cd1—N2 | 2.375 (2) | C12—O6B | 1.427 (6) |
Cd1—O2 | 2.3862 (19) | C12—C11 | 1.502 (4) |
Cd1—N1 | 2.392 (2) | C12—H12A | 0.9700 |
Cd1—O3 | 2.415 (2) | C12—H12B | 0.9700 |
N2—C7 | 1.482 (3) | O6A—H6A | 0.8780 |
N2—C11 | 1.486 (3) | O6A—H6B | 1.0354 |
N2—C9 | 1.487 (3) | O6B—H6A | 1.1021 |
O1—C2B | 1.411 (4) | O6B—H6B | 0.8844 |
O1—C2A | 1.411 (6) | C7—C8 | 1.522 (4) |
O1—H1 | 0.8586 | C7—H7A | 0.9700 |
O2—C4B | 1.435 (4) | C7—H7B | 0.9700 |
O2—C4A | 1.449 (6) | C8—H8A | 0.9700 |
O2—H2 | 0.8576 | C8—H8B | 0.9700 |
O3—C6B | 1.414 (5) | C9—C10 | 1.510 (4) |
O3—C6A | 1.421 (6) | C9—H9A | 0.9700 |
O3—H3 | 0.8570 | C9—H9B | 0.9700 |
O4—C8 | 1.429 (4) | C10—H10A | 0.9700 |
O4—H4 | 0.8596 | C10—H10B | 0.9700 |
O5—C10 | 1.422 (3) | C11—H11A | 0.9700 |
O5—H5 | 0.8586 | C11—H11B | 0.9700 |
N1—C5B | 1.473 (3) | S2—O12 | 1.433 (2) |
N1—C3A | 1.476 (4) | S2—O11 | 1.439 (2) |
N1—C1B | 1.477 (3) | S2—N4 | 1.621 (2) |
N1—C5A | 1.484 (4) | S2—C26 | 1.759 (3) |
N1—C1A | 1.492 (4) | N4—C20 | 1.337 (3) |
N1—C3B | 1.495 (3) | O10—C20 | 1.246 (3) |
C1A—C2A | 1.511 (7) | C20—C21 | 1.493 (3) |
C1A—H1A1 | 0.9700 | C21—C26 | 1.375 (3) |
C1A—H1A2 | 0.9700 | C21—C22 | 1.389 (3) |
C2A—H2A1 | 0.9700 | C22—C23 | 1.385 (4) |
C2A—H2A2 | 0.9700 | C22—H22 | 0.9300 |
C3A—C4A | 1.509 (7) | C23—C24 | 1.387 (4) |
C3A—H3A1 | 0.9700 | C23—H23 | 0.9300 |
C3A—H3A2 | 0.9700 | C24—C25 | 1.383 (4) |
C4A—H4A1 | 0.9700 | C24—H24 | 0.9300 |
C4A—H4A2 | 0.9700 | C25—C26 | 1.391 (4) |
C5A—C6A | 1.491 (7) | C25—H25 | 0.9300 |
C5A—H5A1 | 0.9700 | S1—O8 | 1.432 (2) |
C5A—H5A2 | 0.9700 | S1—O9 | 1.447 (2) |
C6A—H6A1 | 0.9700 | S1—N3 | 1.619 (3) |
C6A—H6A2 | 0.9700 | S1—C19 | 1.758 (3) |
C1B—C2B | 1.516 (6) | O7—C13 | 1.236 (3) |
C1B—H1B1 | 0.9700 | N3—C13 | 1.344 (3) |
C1B—H1B2 | 0.9700 | C13—C14 | 1.505 (4) |
C2B—H2B1 | 0.9700 | C14—C19 | 1.379 (3) |
C2B—H2B2 | 0.9700 | C14—C15 | 1.380 (4) |
C3B—C4B | 1.501 (6) | C15—C16 | 1.399 (4) |
C3B—H3B1 | 0.9700 | C15—H15 | 0.9300 |
C3B—H3B2 | 0.9700 | C16—C17 | 1.387 (5) |
C4B—H4B1 | 0.9700 | C16—H16 | 0.9300 |
C4B—H4B2 | 0.9700 | C17—C18 | 1.379 (5) |
C5B—C6B | 1.492 (6) | C17—H17 | 0.9300 |
C5B—H5B1 | 0.9700 | C18—C19 | 1.382 (4) |
C5B—H5B2 | 0.9700 | C18—H18 | 0.9300 |
| | | |
O4—Cd1—O5 | 102.28 (8) | C4B—C3B—H3B2 | 109.0 |
O4—Cd1—O1 | 81.81 (7) | H3B1—C3B—H3B2 | 107.8 |
O5—Cd1—O1 | 72.95 (7) | O2—C4B—C3B | 106.4 (3) |
O4—Cd1—N2 | 74.86 (7) | O2—C4B—H4B1 | 110.4 |
O5—Cd1—N2 | 73.64 (7) | C3B—C4B—H4B1 | 110.4 |
O1—Cd1—N2 | 133.59 (7) | O2—C4B—H4B2 | 110.4 |
O4—Cd1—O2 | 166.01 (7) | C3B—C4B—H4B2 | 110.4 |
O5—Cd1—O2 | 82.73 (8) | H4B1—C4B—H4B2 | 108.6 |
O1—Cd1—O2 | 112.18 (7) | N1—C5B—C6B | 113.5 (3) |
N2—Cd1—O2 | 94.39 (7) | N1—C5B—H5B1 | 108.9 |
O4—Cd1—N1 | 111.99 (8) | C6B—C5B—H5B1 | 108.9 |
O5—Cd1—N1 | 125.92 (7) | N1—C5B—H5B2 | 108.9 |
O1—Cd1—N1 | 72.11 (7) | C6B—C5B—H5B2 | 108.9 |
N2—Cd1—N1 | 154.11 (7) | H5B1—C5B—H5B2 | 107.7 |
O2—Cd1—N1 | 73.97 (8) | O3—C6B—C5B | 111.3 (4) |
O4—Cd1—O3 | 80.07 (8) | O3—C6B—H6B1 | 109.4 |
O5—Cd1—O3 | 158.08 (7) | C5B—C6B—H6B1 | 109.4 |
O1—Cd1—O3 | 128.66 (7) | O3—C6B—H6B2 | 109.4 |
N2—Cd1—O3 | 86.21 (7) | C5B—C6B—H6B2 | 109.4 |
O2—Cd1—O3 | 90.46 (8) | H6B1—C6B—H6B2 | 108.0 |
N1—Cd1—O3 | 71.15 (7) | O6A—C12—O6B | 20.1 (8) |
C7—N2—C11 | 111.6 (2) | O6A—C12—C11 | 111.8 (7) |
C7—N2—C9 | 111.2 (2) | O6B—C12—C11 | 106.9 (9) |
C11—N2—C9 | 112.4 (2) | O6A—C12—H12A | 109.3 |
C7—N2—Cd1 | 106.24 (15) | O6B—C12—H12A | 127.9 |
C11—N2—Cd1 | 106.04 (15) | C11—C12—H12A | 109.3 |
C9—N2—Cd1 | 108.97 (14) | O6A—C12—H12B | 109.3 |
C2B—O1—C2A | 18.0 (6) | O6B—C12—H12B | 93.8 |
C2B—O1—Cd1 | 112.7 (2) | C11—C12—H12B | 109.3 |
C2A—O1—Cd1 | 116.4 (2) | H12A—C12—H12B | 107.9 |
C2B—O1—H1 | 109.2 | C12—O6A—H6A | 108.6 |
Cd1—O1—H1 | 122.1 | C12—O6A—H6B | 99.5 |
C4B—O2—C4A | 24.6 (5) | C12—O6B—H6A | 96.5 |
C4B—O2—Cd1 | 109.0 (2) | C12—O6B—H6B | 107.9 |
C4A—O2—Cd1 | 112.5 (3) | N2—C7—C8 | 112.9 (2) |
C4B—O2—H2 | 109.7 | N2—C7—H7A | 109.0 |
Cd1—O2—H2 | 129.1 | C8—C7—H7A | 109.0 |
C6B—O3—C6A | 28.8 (5) | N2—C7—H7B | 109.0 |
C6B—O3—Cd1 | 115.8 (2) | C8—C7—H7B | 109.0 |
C6A—O3—Cd1 | 105.8 (4) | H7A—C7—H7B | 107.8 |
C6B—O3—H3 | 109.2 | O4—C8—C7 | 108.6 (2) |
Cd1—O3—H3 | 131.1 | O4—C8—H8A | 110.0 |
C8—O4—Cd1 | 113.66 (15) | C7—C8—H8A | 110.0 |
C8—O4—H4 | 109.5 | O4—C8—H8B | 110.0 |
Cd1—O4—H4 | 121.2 | C7—C8—H8B | 110.0 |
C10—O5—Cd1 | 109.84 (16) | H8A—C8—H8B | 108.3 |
C10—O5—H5 | 109.1 | N2—C9—C10 | 111.5 (2) |
Cd1—O5—H5 | 113.4 | N2—C9—H9A | 109.3 |
C5B—N1—C3A | 131.9 (7) | C10—C9—H9A | 109.3 |
C5B—N1—C1B | 113.3 (3) | N2—C9—H9B | 109.3 |
C3A—N1—C1B | 82.9 (5) | C10—C9—H9B | 109.3 |
C5B—N1—C5A | 20.6 (6) | H9A—C9—H9B | 108.0 |
C3A—N1—C5A | 113.7 (8) | O5—C10—C9 | 107.3 (2) |
C1B—N1—C5A | 126.5 (6) | O5—C10—H10A | 110.3 |
C5B—N1—C1A | 81.0 (4) | C9—C10—H10A | 110.3 |
C3A—N1—C1A | 116.7 (6) | O5—C10—H10B | 110.3 |
C1B—N1—C1A | 36.0 (4) | C9—C10—H10B | 110.3 |
C5A—N1—C1A | 99.0 (7) | H10A—C10—H10B | 108.5 |
C5B—N1—C3B | 111.1 (3) | N2—C11—C12 | 118.2 (2) |
C3A—N1—C3B | 27.4 (5) | N2—C11—H11A | 107.8 |
C1B—N1—C3B | 109.0 (3) | C12—C11—H11A | 107.8 |
C5A—N1—C3B | 90.8 (5) | N2—C11—H11B | 107.8 |
C1A—N1—C3B | 139.0 (6) | C12—C11—H11B | 107.8 |
C5B—N1—Cd1 | 106.3 (3) | H11A—C11—H11B | 107.1 |
C3A—N1—Cd1 | 109.8 (5) | O12—S2—O11 | 115.79 (15) |
C1B—N1—Cd1 | 109.9 (2) | O12—S2—N4 | 111.44 (15) |
C5A—N1—Cd1 | 110.6 (4) | O11—S2—N4 | 110.23 (14) |
C1A—N1—Cd1 | 106.4 (5) | O12—S2—C26 | 110.81 (14) |
C3B—N1—Cd1 | 107.1 (2) | O11—S2—C26 | 110.79 (14) |
N1—C1A—C2A | 111.2 (5) | N4—S2—C26 | 96.06 (12) |
N1—C1A—H1A1 | 109.4 | C20—N4—S2 | 112.11 (18) |
C2A—C1A—H1A1 | 109.4 | O10—C20—N4 | 123.4 (2) |
N1—C1A—H1A2 | 109.4 | O10—C20—C21 | 123.4 (2) |
C2A—C1A—H1A2 | 109.4 | N4—C20—C21 | 113.2 (2) |
H1A1—C1A—H1A2 | 108.0 | C26—C21—C22 | 120.2 (2) |
O1—C2A—C1A | 110.4 (6) | C26—C21—C20 | 111.1 (2) |
O1—C2A—H2A1 | 109.6 | C22—C21—C20 | 128.8 (2) |
C1A—C2A—H2A1 | 109.6 | C23—C22—C21 | 118.3 (3) |
O1—C2A—H2A2 | 109.6 | C23—C22—H22 | 120.8 |
C1A—C2A—H2A2 | 109.6 | C21—C22—H22 | 120.8 |
H2A1—C2A—H2A2 | 108.1 | C22—C23—C24 | 120.7 (3) |
N1—C3A—C4A | 112.1 (5) | C22—C23—H23 | 119.7 |
N1—C3A—H3A1 | 109.2 | C24—C23—H23 | 119.7 |
C4A—C3A—H3A1 | 109.2 | C25—C24—C23 | 121.6 (3) |
N1—C3A—H3A2 | 109.2 | C25—C24—H24 | 119.2 |
C4A—C3A—H3A2 | 109.2 | C23—C24—H24 | 119.2 |
H3A1—C3A—H3A2 | 107.9 | C24—C25—C26 | 116.9 (3) |
O2—C4A—C3A | 115.1 (7) | C24—C25—H25 | 121.6 |
O2—C4A—H4A1 | 108.5 | C26—C25—H25 | 121.6 |
C3A—C4A—H4A1 | 108.5 | C21—C26—C25 | 122.3 (2) |
O2—C4A—H4A2 | 108.5 | C21—C26—S2 | 107.56 (18) |
C3A—C4A—H4A2 | 108.5 | C25—C26—S2 | 130.1 (2) |
H4A1—C4A—H4A2 | 107.5 | O8—S1—O9 | 114.72 (14) |
N1—C5A—C6A | 114.0 (5) | O8—S1—N3 | 111.56 (15) |
N1—C5A—H5A1 | 108.8 | O9—S1—N3 | 110.80 (14) |
C6A—C5A—H5A1 | 108.8 | O8—S1—C19 | 112.76 (14) |
N1—C5A—H5A2 | 108.8 | O9—S1—C19 | 108.56 (13) |
C6A—C5A—H5A2 | 108.8 | N3—S1—C19 | 97.04 (12) |
H5A1—C5A—H5A2 | 107.6 | C13—N3—S1 | 111.34 (19) |
O3—C6A—C5A | 106.4 (8) | O7—C13—N3 | 123.7 (3) |
O3—C6A—H6A1 | 110.5 | O7—C13—C14 | 122.9 (2) |
C5A—C6A—H6A1 | 110.5 | N3—C13—C14 | 113.4 (2) |
O3—C6A—H6A2 | 110.5 | C19—C14—C15 | 120.1 (2) |
C5A—C6A—H6A2 | 110.5 | C19—C14—C13 | 110.9 (2) |
H6A1—C6A—H6A2 | 108.6 | C15—C14—C13 | 129.0 (2) |
N1—C1B—C2B | 111.2 (3) | C14—C15—C16 | 117.8 (3) |
N1—C1B—H1B1 | 109.4 | C14—C15—H15 | 121.1 |
C2B—C1B—H1B1 | 109.4 | C16—C15—H15 | 121.1 |
N1—C1B—H1B2 | 109.4 | C17—C16—C15 | 121.2 (3) |
C2B—C1B—H1B2 | 109.4 | C17—C16—H16 | 119.4 |
H1B1—C1B—H1B2 | 108.0 | C15—C16—H16 | 119.4 |
O1—C2B—C1B | 106.9 (3) | C18—C17—C16 | 120.7 (3) |
O1—C2B—H2B1 | 110.3 | C18—C17—H17 | 119.6 |
C1B—C2B—H2B1 | 110.3 | C16—C17—H17 | 119.6 |
O1—C2B—H2B2 | 110.3 | C17—C18—C19 | 117.4 (3) |
C1B—C2B—H2B2 | 110.3 | C17—C18—H18 | 121.3 |
H2B1—C2B—H2B2 | 108.6 | C19—C18—H18 | 121.3 |
N1—C3B—C4B | 112.9 (3) | C14—C19—C18 | 122.7 (2) |
N1—C3B—H3B1 | 109.0 | C14—C19—S1 | 107.26 (19) |
C4B—C3B—H3B1 | 109.0 | C18—C19—S1 | 129.8 (2) |
N1—C3B—H3B2 | 109.0 | | |
| | | |
O4—Cd1—N2—C7 | 17.88 (16) | C1B—N1—C3A—C4A | 150.0 (12) |
O5—Cd1—N2—C7 | 125.88 (17) | C5A—N1—C3A—C4A | −83.2 (14) |
O1—Cd1—N2—C7 | 80.41 (18) | C1A—N1—C3A—C4A | 162.5 (9) |
O2—Cd1—N2—C7 | −153.02 (16) | C3B—N1—C3A—C4A | −47.6 (5) |
N1—Cd1—N2—C7 | −91.4 (2) | Cd1—N1—C3A—C4A | 41.4 (13) |
O3—Cd1—N2—C7 | −62.85 (16) | C4B—O2—C4A—C3A | −61.3 (9) |
O4—Cd1—N2—C11 | 136.77 (18) | Cd1—O2—C4A—C3A | 25.4 (12) |
O5—Cd1—N2—C11 | −115.23 (17) | N1—C3A—C4A—O2 | −46.0 (16) |
O1—Cd1—N2—C11 | −160.69 (15) | C5B—N1—C5A—C6A | −61.9 (9) |
O2—Cd1—N2—C11 | −34.13 (17) | C3A—N1—C5A—C6A | 143.8 (9) |
N1—Cd1—N2—C11 | 27.4 (3) | C1B—N1—C5A—C6A | −117.2 (10) |
O3—Cd1—N2—C11 | 56.05 (17) | C1A—N1—C5A—C6A | −91.7 (13) |
O4—Cd1—N2—C9 | −102.05 (17) | C3B—N1—C5A—C6A | 128.3 (11) |
O5—Cd1—N2—C9 | 5.95 (16) | Cd1—N1—C5A—C6A | 19.7 (13) |
O1—Cd1—N2—C9 | −39.51 (19) | C6B—O3—C6A—C5A | −54.7 (6) |
O2—Cd1—N2—C9 | 87.05 (17) | Cd1—O3—C6A—C5A | 60.6 (9) |
N1—Cd1—N2—C9 | 148.63 (18) | N1—C5A—C6A—O3 | −55.4 (14) |
O3—Cd1—N2—C9 | 177.23 (17) | C5B—N1—C1B—C2B | 79.7 (5) |
O4—Cd1—O1—C2B | −94.7 (3) | C3A—N1—C1B—C2B | −147.5 (7) |
O5—Cd1—O1—C2B | 159.7 (3) | C5A—N1—C1B—C2B | 98.1 (6) |
N2—Cd1—O1—C2B | −154.7 (3) | C1A—N1—C1B—C2B | 51.8 (7) |
O2—Cd1—O1—C2B | 85.2 (3) | C3B—N1—C1B—C2B | −156.0 (4) |
N1—Cd1—O1—C2B | 21.6 (3) | Cd1—N1—C1B—C2B | −39.0 (4) |
O3—Cd1—O1—C2B | −24.5 (3) | C2A—O1—C2B—C1B | 57.7 (7) |
O4—Cd1—O1—C2A | −114.1 (6) | Cd1—O1—C2B—C1B | −48.3 (4) |
O5—Cd1—O1—C2A | 140.3 (6) | N1—C1B—C2B—O1 | 58.8 (5) |
N2—Cd1—O1—C2A | −174.0 (6) | C5B—N1—C3B—C4B | −154.9 (4) |
O2—Cd1—O1—C2A | 65.9 (6) | C3A—N1—C3B—C4B | 61.1 (11) |
N1—Cd1—O1—C2A | 2.3 (6) | C1B—N1—C3B—C4B | 79.6 (5) |
O3—Cd1—O1—C2A | −43.8 (6) | C5A—N1—C3B—C4B | −151.1 (7) |
O4—Cd1—O2—C4B | 141.3 (4) | C1A—N1—C3B—C4B | 104.2 (6) |
O5—Cd1—O2—C4B | −106.7 (3) | Cd1—N1—C3B—C4B | −39.2 (4) |
O1—Cd1—O2—C4B | −38.5 (3) | C4A—O2—C4B—C3B | 51.3 (5) |
N2—Cd1—O2—C4B | −179.6 (3) | Cd1—O2—C4B—C3B | −51.3 (4) |
N1—Cd1—O2—C4B | 23.9 (3) | N1—C3B—C4B—O2 | 63.0 (5) |
O3—Cd1—O2—C4B | 94.2 (3) | C3A—N1—C5B—C6B | 85.2 (7) |
O4—Cd1—O2—C4A | 115.1 (7) | C1B—N1—C5B—C6B | −173.0 (4) |
O5—Cd1—O2—C4A | −132.8 (6) | C5A—N1—C5B—C6B | 53.0 (13) |
O1—Cd1—O2—C4A | −64.6 (6) | C1A—N1—C5B—C6B | −156.8 (7) |
N2—Cd1—O2—C4A | 154.3 (6) | C3B—N1—C5B—C6B | 63.9 (6) |
N1—Cd1—O2—C4A | −2.2 (6) | Cd1—N1—C5B—C6B | −52.3 (6) |
O3—Cd1—O2—C4A | 68.0 (6) | C6A—O3—C6B—C5B | 60.4 (5) |
O4—Cd1—O3—C6B | 108.5 (3) | Cd1—O3—C6B—C5B | −14.9 (6) |
O5—Cd1—O3—C6B | −153.3 (3) | N1—C5B—C6B—O3 | 46.1 (7) |
O1—Cd1—O3—C6B | 37.5 (3) | C11—N2—C7—C8 | −159.9 (2) |
N2—Cd1—O3—C6B | −176.2 (3) | C9—N2—C7—C8 | 73.7 (3) |
O2—Cd1—O3—C6B | −81.8 (3) | Cd1—N2—C7—C8 | −44.7 (3) |
N1—Cd1—O3—C6B | −9.0 (3) | Cd1—O4—C8—C7 | −36.7 (3) |
O4—Cd1—O3—C6A | 79.5 (5) | N2—C7—C8—O4 | 56.2 (3) |
O5—Cd1—O3—C6A | 177.8 (5) | C7—N2—C9—C10 | −152.3 (2) |
O1—Cd1—O3—C6A | 8.5 (5) | C11—N2—C9—C10 | 81.7 (3) |
N2—Cd1—O3—C6A | 154.8 (5) | Cd1—N2—C9—C10 | −35.5 (2) |
O2—Cd1—O3—C6A | −110.8 (5) | Cd1—O5—C10—C9 | −52.1 (3) |
N1—Cd1—O3—C6A | −37.9 (5) | N2—C9—C10—O5 | 59.8 (3) |
O5—Cd1—O4—C8 | −58.40 (19) | C7—N2—C11—C12 | −44.3 (4) |
O1—Cd1—O4—C8 | −128.9 (2) | C9—N2—C11—C12 | 81.4 (3) |
N2—Cd1—O4—C8 | 10.65 (18) | Cd1—N2—C11—C12 | −159.6 (2) |
O2—Cd1—O4—C8 | 51.3 (4) | O6A—C12—C11—N2 | −46.2 (9) |
N1—Cd1—O4—C8 | 164.26 (18) | O6B—C12—C11—N2 | −66.9 (9) |
O3—Cd1—O4—C8 | 99.38 (19) | O12—S2—N4—C20 | −115.6 (2) |
O4—Cd1—O5—C10 | 95.32 (18) | O11—S2—N4—C20 | 114.4 (2) |
O1—Cd1—O5—C10 | 172.66 (19) | C26—S2—N4—C20 | −0.4 (2) |
N2—Cd1—O5—C10 | 25.35 (18) | S2—N4—C20—O10 | −179.3 (3) |
O2—Cd1—O5—C10 | −71.42 (18) | S2—N4—C20—C21 | 0.3 (3) |
N1—Cd1—O5—C10 | −135.56 (17) | O10—C20—C21—C26 | 179.6 (3) |
O3—Cd1—O5—C10 | 1.4 (3) | N4—C20—C21—C26 | 0.0 (4) |
O4—Cd1—N1—C5B | −39.9 (3) | O10—C20—C21—C22 | −0.1 (5) |
O5—Cd1—N1—C5B | −165.0 (3) | N4—C20—C21—C22 | −179.7 (3) |
O1—Cd1—N1—C5B | −112.9 (3) | C26—C21—C22—C23 | −0.1 (5) |
N2—Cd1—N1—C5B | 60.9 (3) | C20—C21—C22—C23 | 179.6 (3) |
O2—Cd1—N1—C5B | 126.7 (3) | C21—C22—C23—C24 | −0.5 (5) |
O3—Cd1—N1—C5B | 30.6 (3) | C22—C23—C24—C25 | 0.8 (6) |
O4—Cd1—N1—C3A | 172.5 (6) | C23—C24—C25—C26 | −0.4 (5) |
O5—Cd1—N1—C3A | 47.3 (6) | C22—C21—C26—C25 | 0.5 (4) |
O1—Cd1—N1—C3A | 99.4 (6) | C20—C21—C26—C25 | −179.2 (3) |
N2—Cd1—N1—C3A | −86.8 (6) | C22—C21—C26—S2 | 179.5 (2) |
O2—Cd1—N1—C3A | −20.9 (6) | C20—C21—C26—S2 | −0.3 (3) |
O3—Cd1—N1—C3A | −117.1 (6) | C24—C25—C26—C21 | −0.2 (5) |
O4—Cd1—N1—C1B | 83.0 (2) | C24—C25—C26—S2 | −178.9 (3) |
O5—Cd1—N1—C1B | −42.1 (3) | O12—S2—C26—C21 | 116.1 (2) |
O1—Cd1—N1—C1B | 10.0 (2) | O11—S2—C26—C21 | −114.0 (2) |
N2—Cd1—N1—C1B | −176.2 (2) | N4—S2—C26—C21 | 0.4 (2) |
O2—Cd1—N1—C1B | −110.3 (2) | O12—S2—C26—C25 | −65.1 (3) |
O3—Cd1—N1—C1B | 153.5 (2) | O11—S2—C26—C25 | 64.9 (3) |
O4—Cd1—N1—C5A | −61.2 (6) | N4—S2—C26—C25 | 179.2 (3) |
O5—Cd1—N1—C5A | 173.7 (6) | O8—S1—N3—C13 | 117.3 (2) |
O1—Cd1—N1—C5A | −134.2 (6) | O9—S1—N3—C13 | −113.5 (2) |
N2—Cd1—N1—C5A | 39.6 (7) | C19—S1—N3—C13 | −0.6 (2) |
O2—Cd1—N1—C5A | 105.4 (6) | S1—N3—C13—O7 | −178.5 (3) |
O3—Cd1—N1—C5A | 9.3 (6) | S1—N3—C13—C14 | 1.6 (3) |
O4—Cd1—N1—C1A | 45.3 (4) | O7—C13—C14—C19 | 178.0 (3) |
O5—Cd1—N1—C1A | −79.8 (4) | N3—C13—C14—C19 | −2.1 (4) |
O1—Cd1—N1—C1A | −27.7 (4) | O7—C13—C14—C15 | −4.6 (5) |
N2—Cd1—N1—C1A | 146.1 (4) | N3—C13—C14—C15 | 175.3 (3) |
O2—Cd1—N1—C1A | −148.1 (4) | C19—C14—C15—C16 | 0.3 (5) |
O3—Cd1—N1—C1A | 115.8 (4) | C13—C14—C15—C16 | −176.9 (3) |
O4—Cd1—N1—C3B | −158.7 (2) | C14—C15—C16—C17 | 0.6 (6) |
O5—Cd1—N1—C3B | 76.1 (2) | C15—C16—C17—C18 | −1.1 (6) |
O1—Cd1—N1—C3B | 128.2 (2) | C16—C17—C18—C19 | 0.6 (5) |
N2—Cd1—N1—C3B | −58.0 (3) | C15—C14—C19—C18 | −0.8 (4) |
O2—Cd1—N1—C3B | 7.9 (2) | C13—C14—C19—C18 | 176.9 (3) |
O3—Cd1—N1—C3B | −88.3 (2) | C15—C14—C19—S1 | −176.1 (2) |
C5B—N1—C1A—C2A | 155.8 (10) | C13—C14—C19—S1 | 1.6 (3) |
C3A—N1—C1A—C2A | −71.6 (13) | C17—C18—C19—C14 | 0.3 (5) |
C1B—N1—C1A—C2A | −50.0 (5) | C17—C18—C19—S1 | 174.5 (3) |
C5A—N1—C1A—C2A | 166.0 (8) | O8—S1—C19—C14 | −117.6 (2) |
C3B—N1—C1A—C2A | −92.2 (10) | O9—S1—C19—C14 | 114.1 (2) |
Cd1—N1—C1A—C2A | 51.4 (9) | N3—S1—C19—C14 | −0.7 (2) |
C2B—O1—C2A—C1A | −58.2 (7) | O8—S1—C19—C18 | 67.5 (3) |
Cd1—O1—C2A—C1A | 23.9 (10) | O9—S1—C19—C18 | −60.8 (3) |
N1—C1A—C2A—O1 | −51.3 (12) | N3—S1—C19—C18 | −175.5 (3) |
C5B—N1—C3A—C4A | −95.0 (12) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O10 | 0.86 | 1.90 | 2.749 (3) | 171 |
O2—H2···O7i | 0.86 | 1.83 | 2.679 (3) | 173 |
O3—H3···N3ii | 0.86 | 1.95 | 2.804 (3) | 178 |
O4—H4···O10iii | 0.86 | 1.86 | 2.715 (3) | 175 |
O5—H5···N4 | 0.86 | 1.86 | 2.714 (3) | 172 |
O6A—H6A···O9 | 0.88 | 1.97 | 2.778 (15) | 152 |
O6B—H6B···O9 | 0.88 | 1.93 | 2.78 (2) | 162 |
Symmetry codes: (i) −x, −y, −z−1; (ii) x, y, z+1; (iii) −x, −y+1, −z+1. |
(II) bis(triethanolamine)-
κ3O,
N,
O';
κ4O,
N,
O',
O''-mercury(II) 1,2-bensisothiazol-3(2
H)-onate
1,1-dioxide
top
Crystal data top
[Hg(C6H15NO3)2]2C7H4NO3S | Z = 2 |
Mr = 863.31 | F(000) = 860 |
Triclinic, P1 | Dx = 1.871 Mg m−3 |
a = 12.588 (2) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 15.934 (3) Å | Cell parameters from 25 reflections |
c = 7.9944 (14) Å | θ = 20.4–26.8° |
α = 91.791 (14)° | µ = 5.23 mm−1 |
β = 91.343 (14)° | T = 293 K |
γ = 72.965 (13)° | Thin plate, colourless |
V = 1532.2 (4) Å3 | 0.50 × 0.35 × 0.10 mm |
Data collection top
Rigaku AFC-7S diffractometer | 5241 reflections with I > 2σ(I) |
Radiation source: X-ray tube | Rint = 0.042 |
Graphite monochromator | θmax = 32.5°, θmin = 2.4° |
ω/2θ scans | h = 0→19 |
Absorption correction: ψ-scan (North et al., 1968) | k = −23→24 |
Tmin = 0.113, Tmax = 0.593 | l = −12→12 |
11526 measured reflections | 3 standard reflections every 150 reflections |
11091 independent reflections | intensity decay: 4.1% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.159 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0765P)2] where P = (Fo2 + 2Fc2)/3 |
11091 reflections | (Δ/σ)max = 0.001 |
412 parameters | Δρmax = 1.94 e Å−3 |
0 restraints | Δρmin = −3.76 e Å−3 |
Crystal data top
[Hg(C6H15NO3)2]2C7H4NO3S | γ = 72.965 (13)° |
Mr = 863.31 | V = 1532.2 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 12.588 (2) Å | Mo Kα radiation |
b = 15.934 (3) Å | µ = 5.23 mm−1 |
c = 7.9944 (14) Å | T = 293 K |
α = 91.791 (14)° | 0.50 × 0.35 × 0.10 mm |
β = 91.343 (14)° | |
Data collection top
Rigaku AFC-7S diffractometer | 5241 reflections with I > 2σ(I) |
Absorption correction: ψ-scan (North et al., 1968) | Rint = 0.042 |
Tmin = 0.113, Tmax = 0.593 | 3 standard reflections every 150 reflections |
11526 measured reflections | intensity decay: 4.1% |
11091 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.159 | H-atom parameters constrained |
S = 0.99 | Δρmax = 1.94 e Å−3 |
11091 reflections | Δρmin = −3.76 e Å−3 |
412 parameters | |
Special details top
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Hg1 | −0.01084 (2) | 0.25302 (2) | 0.81924 (3) | 0.03477 (9) | |
O1 | −0.0417 (7) | 0.2680 (4) | 1.1382 (8) | 0.087 (3) | |
H1 | −0.0566 | 0.2312 | 1.1994 | 0.131* | |
O2 | 0.0262 (5) | 0.3673 (3) | 0.5962 (7) | 0.0478 (13) | |
H2 | 0.0927 | 0.3614 | 0.5653 | 0.072* | |
O3 | −0.1908 (5) | 0.2491 (4) | 0.6521 (7) | 0.0537 (15) | |
H3 | −0.1989 | 0.2336 | 0.5506 | 0.081* | |
O4 | −0.0351 (5) | 0.1171 (4) | 0.9305 (7) | 0.0503 (14) | |
H4 | −0.1004 | 0.1193 | 0.9615 | 0.075* | |
O5 | 0.1759 (5) | 0.2629 (4) | 0.9123 (7) | 0.0552 (15) | |
H5 | 0.1792 | 0.2693 | 1.0194 | 0.083* | |
O6 | 0.2015 (6) | 0.0232 (4) | 0.3932 (7) | 0.0565 (15) | |
H6 | 0.2457 | 0.0008 | 0.3128 | 0.085* | |
N1 | −0.1369 (5) | 0.3825 (4) | 0.8683 (7) | 0.0319 (12) | |
N2 | 0.1078 (5) | 0.1446 (4) | 0.6735 (6) | 0.0306 (12) | |
C1 | −0.1211 (10) | 0.4127 (6) | 1.0440 (11) | 0.066 (3) | |
H1A | −0.0547 | 0.4319 | 1.0474 | 0.079* | |
H1B | −0.1833 | 0.4638 | 1.0694 | 0.079* | |
C2 | −0.1113 (9) | 0.3506 (6) | 1.1770 (10) | 0.058 (2) | |
H2A | −0.0835 | 0.3730 | 1.2777 | 0.069* | |
H2B | −0.1845 | 0.3458 | 1.2006 | 0.069* | |
C3 | −0.1209 (8) | 0.4505 (6) | 0.7580 (14) | 0.067 (3) | |
H3A | −0.1683 | 0.4526 | 0.6599 | 0.080* | |
H3B | −0.1474 | 0.5068 | 0.8167 | 0.080* | |
C4 | −0.0090 (8) | 0.4415 (5) | 0.7009 (11) | 0.055 (2) | |
H4A | −0.0083 | 0.4933 | 0.6408 | 0.066* | |
H4B | 0.0413 | 0.4361 | 0.7964 | 0.066* | |
C5 | −0.2481 (8) | 0.3705 (7) | 0.8487 (13) | 0.066 (3) | |
H5A | −0.3027 | 0.4276 | 0.8611 | 0.079* | |
H5B | −0.2586 | 0.3350 | 0.9398 | 0.079* | |
C6 | −0.2722 (8) | 0.3290 (7) | 0.6886 (12) | 0.067 (3) | |
H6A | −0.3440 | 0.3184 | 0.6954 | 0.081* | |
H6B | −0.2761 | 0.3690 | 0.5982 | 0.081* | |
C7 | 0.1098 (7) | 0.0582 (5) | 0.7416 (10) | 0.0416 (17) | |
H7A | 0.1607 | 0.0457 | 0.8368 | 0.050* | |
H7B | 0.1375 | 0.0127 | 0.6568 | 0.050* | |
C8 | −0.0038 (7) | 0.0556 (5) | 0.7958 (11) | 0.0496 (19) | |
H8A | −0.0571 | 0.0712 | 0.7040 | 0.060* | |
H8B | −0.0005 | −0.0028 | 0.8314 | 0.060* | |
C9 | 0.2205 (6) | 0.1581 (5) | 0.6886 (9) | 0.0411 (16) | |
H9A | 0.2753 | 0.1049 | 0.6501 | 0.049* | |
H9B | 0.2230 | 0.2049 | 0.6155 | 0.049* | |
C10 | 0.2513 (7) | 0.1805 (6) | 0.8620 (10) | 0.0497 (19) | |
H10A | 0.2471 | 0.1353 | 0.9379 | 0.060* | |
H10B | 0.3269 | 0.1843 | 0.8649 | 0.060* | |
C11 | 0.0661 (6) | 0.1541 (5) | 0.4933 (8) | 0.0371 (15) | |
H11A | 0.0040 | 0.1298 | 0.4826 | 0.045* | |
H11B | 0.0377 | 0.2162 | 0.4711 | 0.045* | |
C12 | 0.1472 (8) | 0.1124 (6) | 0.3612 (10) | 0.051 (2) | |
H12A | 0.1087 | 0.1165 | 0.2538 | 0.061* | |
H12B | 0.2021 | 0.1439 | 0.3548 | 0.061* | |
S1 | 0.34415 (17) | −0.11775 (13) | 0.0159 (2) | 0.0425 (4) | |
N3 | 0.2483 (6) | −0.1548 (5) | −0.0652 (8) | 0.0458 (15) | |
O7 | 0.1969 (5) | −0.1979 (4) | −0.3206 (7) | 0.0576 (16) | |
O8 | 0.2977 (5) | −0.0293 (4) | 0.0785 (7) | 0.0583 (16) | |
O9 | 0.4123 (6) | −0.1776 (4) | 0.1336 (7) | 0.0664 (19) | |
C13 | 0.2613 (6) | −0.1702 (5) | −0.2315 (9) | 0.0399 (16) | |
C14 | 0.3608 (6) | −0.1490 (5) | −0.2961 (8) | 0.0344 (14) | |
C15 | 0.3982 (7) | −0.1556 (6) | −0.4592 (9) | 0.0472 (19) | |
H15 | 0.3618 | −0.1771 | −0.5454 | 0.057* | |
C16 | 0.4906 (8) | −0.1295 (7) | −0.4895 (10) | 0.059 (2) | |
H16 | 0.5187 | −0.1354 | −0.5972 | 0.070* | |
C17 | 0.5434 (8) | −0.0939 (7) | −0.3604 (12) | 0.059 (2) | |
H17 | 0.6036 | −0.0740 | −0.3846 | 0.071* | |
C18 | 0.5067 (7) | −0.0884 (6) | −0.1982 (10) | 0.0491 (19) | |
H18 | 0.5426 | −0.0671 | −0.1111 | 0.059* | |
C19 | 0.4138 (6) | −0.1161 (5) | −0.1702 (8) | 0.0342 (14) | |
S2 | 0.33536 (17) | 0.39041 (13) | 0.5671 (2) | 0.0412 (4) | |
N4 | 0.2387 (6) | 0.3528 (4) | 0.4873 (8) | 0.0444 (15) | |
O10 | 0.1888 (5) | 0.3063 (5) | 0.2332 (7) | 0.0597 (16) | |
O11 | 0.2893 (5) | 0.4805 (4) | 0.6231 (7) | 0.0561 (15) | |
O12 | 0.4004 (6) | 0.3331 (5) | 0.6901 (7) | 0.072 (2) | |
C20 | 0.2530 (7) | 0.3350 (5) | 0.3209 (9) | 0.0417 (17) | |
C21 | 0.3544 (6) | 0.3536 (5) | 0.2551 (9) | 0.0350 (15) | |
C22 | 0.3912 (7) | 0.3475 (6) | 0.0933 (9) | 0.048 (2) | |
H22 | 0.3545 | 0.3260 | 0.0075 | 0.058* | |
C23 | 0.4826 (8) | 0.3736 (6) | 0.0607 (10) | 0.056 (2) | |
H23 | 0.5079 | 0.3701 | −0.0484 | 0.067* | |
C24 | 0.5383 (7) | 0.4055 (6) | 0.1890 (11) | 0.056 (2) | |
H24 | 0.6004 | 0.4229 | 0.1645 | 0.067* | |
C25 | 0.5028 (6) | 0.4113 (5) | 0.3503 (10) | 0.0462 (18) | |
H25 | 0.5404 | 0.4316 | 0.4366 | 0.055* | |
C26 | 0.4098 (6) | 0.3862 (5) | 0.3808 (8) | 0.0357 (15) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Hg1 | 0.03639 (15) | 0.03228 (14) | 0.03249 (13) | −0.00562 (10) | −0.00007 (9) | −0.00323 (9) |
O1 | 0.142 (7) | 0.053 (4) | 0.042 (3) | 0.011 (4) | −0.001 (4) | 0.008 (3) |
O2 | 0.053 (3) | 0.042 (3) | 0.049 (3) | −0.014 (3) | 0.014 (3) | −0.007 (2) |
O3 | 0.050 (3) | 0.065 (4) | 0.042 (3) | −0.013 (3) | −0.015 (3) | −0.013 (3) |
O4 | 0.046 (3) | 0.057 (3) | 0.048 (3) | −0.015 (3) | 0.014 (3) | 0.006 (3) |
O5 | 0.052 (4) | 0.063 (4) | 0.045 (3) | −0.011 (3) | −0.012 (3) | −0.013 (3) |
O6 | 0.071 (4) | 0.052 (3) | 0.038 (3) | −0.005 (3) | 0.013 (3) | −0.009 (2) |
N1 | 0.031 (3) | 0.036 (3) | 0.026 (3) | −0.003 (2) | 0.003 (2) | 0.002 (2) |
N2 | 0.036 (3) | 0.035 (3) | 0.020 (2) | −0.008 (2) | 0.005 (2) | −0.006 (2) |
C1 | 0.094 (8) | 0.055 (5) | 0.041 (5) | −0.011 (5) | 0.000 (5) | −0.003 (4) |
C2 | 0.087 (7) | 0.048 (5) | 0.038 (4) | −0.020 (5) | 0.005 (4) | −0.004 (4) |
C3 | 0.076 (7) | 0.039 (4) | 0.083 (7) | −0.009 (4) | 0.027 (5) | 0.016 (4) |
C4 | 0.069 (6) | 0.044 (4) | 0.055 (5) | −0.022 (4) | 0.015 (4) | −0.004 (4) |
C5 | 0.046 (5) | 0.070 (6) | 0.073 (6) | −0.004 (4) | 0.005 (5) | −0.003 (5) |
C6 | 0.043 (5) | 0.091 (7) | 0.058 (6) | −0.007 (5) | −0.010 (4) | −0.013 (5) |
C7 | 0.052 (5) | 0.029 (3) | 0.040 (4) | −0.007 (3) | 0.002 (3) | −0.001 (3) |
C8 | 0.060 (5) | 0.046 (4) | 0.050 (5) | −0.025 (4) | 0.002 (4) | 0.007 (4) |
C9 | 0.042 (4) | 0.048 (4) | 0.037 (4) | −0.020 (3) | 0.005 (3) | −0.006 (3) |
C10 | 0.043 (4) | 0.059 (5) | 0.049 (4) | −0.019 (4) | −0.010 (4) | −0.010 (4) |
C11 | 0.045 (4) | 0.043 (4) | 0.021 (3) | −0.011 (3) | −0.003 (3) | −0.008 (3) |
C12 | 0.063 (6) | 0.051 (5) | 0.038 (4) | −0.017 (4) | −0.008 (4) | −0.001 (3) |
S1 | 0.0534 (12) | 0.0487 (10) | 0.0217 (8) | −0.0094 (9) | 0.0025 (7) | −0.0041 (7) |
N3 | 0.048 (4) | 0.060 (4) | 0.032 (3) | −0.019 (3) | 0.009 (3) | −0.001 (3) |
O7 | 0.055 (4) | 0.083 (4) | 0.047 (3) | −0.039 (3) | −0.001 (3) | −0.001 (3) |
O8 | 0.079 (4) | 0.053 (3) | 0.037 (3) | −0.011 (3) | 0.012 (3) | −0.018 (3) |
O9 | 0.086 (5) | 0.073 (4) | 0.026 (3) | −0.001 (4) | −0.011 (3) | 0.006 (3) |
C13 | 0.041 (4) | 0.046 (4) | 0.038 (4) | −0.021 (3) | 0.003 (3) | −0.001 (3) |
C14 | 0.034 (4) | 0.038 (4) | 0.030 (3) | −0.008 (3) | 0.001 (3) | 0.000 (3) |
C15 | 0.060 (5) | 0.060 (5) | 0.027 (3) | −0.026 (4) | 0.005 (3) | −0.006 (3) |
C16 | 0.062 (6) | 0.083 (7) | 0.036 (4) | −0.029 (5) | 0.025 (4) | −0.007 (4) |
C17 | 0.046 (5) | 0.081 (7) | 0.058 (5) | −0.029 (5) | 0.011 (4) | −0.003 (5) |
C18 | 0.046 (5) | 0.059 (5) | 0.046 (4) | −0.022 (4) | −0.005 (4) | −0.008 (4) |
C19 | 0.033 (4) | 0.037 (4) | 0.031 (3) | −0.007 (3) | 0.001 (3) | −0.005 (3) |
S2 | 0.0483 (11) | 0.0522 (11) | 0.0222 (7) | −0.0142 (9) | −0.0025 (7) | −0.0036 (7) |
N4 | 0.052 (4) | 0.054 (4) | 0.033 (3) | −0.025 (3) | 0.005 (3) | −0.003 (3) |
O10 | 0.068 (4) | 0.086 (5) | 0.042 (3) | −0.050 (4) | 0.001 (3) | −0.013 (3) |
O11 | 0.064 (4) | 0.063 (4) | 0.040 (3) | −0.019 (3) | 0.007 (3) | −0.023 (3) |
O12 | 0.083 (5) | 0.096 (5) | 0.027 (3) | −0.010 (4) | −0.015 (3) | 0.013 (3) |
C20 | 0.049 (5) | 0.051 (4) | 0.031 (3) | −0.024 (4) | 0.005 (3) | −0.003 (3) |
C21 | 0.040 (4) | 0.034 (3) | 0.033 (3) | −0.013 (3) | 0.003 (3) | −0.004 (3) |
C22 | 0.059 (5) | 0.065 (5) | 0.028 (3) | −0.030 (4) | 0.006 (3) | −0.013 (3) |
C23 | 0.068 (6) | 0.072 (6) | 0.036 (4) | −0.033 (5) | 0.020 (4) | −0.009 (4) |
C24 | 0.045 (5) | 0.067 (6) | 0.060 (5) | −0.025 (4) | 0.018 (4) | −0.012 (4) |
C25 | 0.038 (4) | 0.058 (5) | 0.045 (4) | −0.019 (4) | −0.001 (3) | −0.012 (4) |
C26 | 0.035 (4) | 0.041 (4) | 0.029 (3) | −0.008 (3) | −0.001 (3) | −0.003 (3) |
Geometric parameters (Å, º) top
Hg1—N1 | 2.234 (5) | C9—C10 | 1.492 (10) |
Hg1—N2 | 2.239 (5) | C9—H9A | 0.9700 |
Hg1—O1 | 2.581 (7) | C9—H9B | 0.9700 |
Hg1—O2 | 2.730 (5) | C10—H10A | 0.9700 |
Hg1—O3 | 2.618 (5) | C10—H10B | 0.9700 |
Hg1—O4 | 2.468 (5) | C11—C12 | 1.486 (11) |
Hg1—O5 | 2.497 (6) | C11—H11A | 0.9700 |
O1—C2 | 1.380 (11) | C11—H11B | 0.9700 |
O1—H1 | 0.8407 | C12—H12A | 0.9700 |
O2—C4 | 1.393 (9) | C12—H12B | 0.9700 |
O2—H2 | 0.8563 | S1—O8 | 1.437 (6) |
O3—C6 | 1.408 (11) | S1—O9 | 1.439 (6) |
O3—H3 | 0.8535 | S1—N3 | 1.607 (7) |
O4—C8 | 1.416 (10) | S1—C19 | 1.749 (7) |
O4—H4 | 0.8547 | N3—C13 | 1.350 (9) |
O5—C10 | 1.429 (10) | O7—C13 | 1.233 (9) |
O5—H5 | 0.8608 | C13—C14 | 1.496 (10) |
O6—C12 | 1.413 (10) | C14—C19 | 1.369 (10) |
O6—H6 | 0.8580 | C14—C15 | 1.387 (10) |
N1—C5 | 1.472 (11) | C15—C16 | 1.375 (12) |
N1—C3 | 1.479 (10) | C15—H15 | 0.9300 |
N1—C1 | 1.498 (10) | C16—C17 | 1.407 (13) |
N2—C7 | 1.490 (9) | C16—H16 | 0.9300 |
N2—C9 | 1.497 (9) | C17—C18 | 1.378 (12) |
N2—C11 | 1.519 (8) | C17—H17 | 0.9300 |
C1—C2 | 1.454 (12) | C18—C19 | 1.390 (11) |
C1—H1A | 0.9700 | C18—H18 | 0.9300 |
C1—H1B | 0.9700 | S2—O12 | 1.432 (6) |
C2—H2A | 0.9700 | S2—O11 | 1.443 (6) |
C2—H2B | 0.9700 | S2—N4 | 1.617 (7) |
C3—C4 | 1.457 (12) | S2—C26 | 1.767 (7) |
C3—H3A | 0.9700 | N4—C20 | 1.356 (9) |
C3—H3B | 0.9700 | O10—C20 | 1.234 (9) |
C4—H4A | 0.9700 | C20—C21 | 1.502 (10) |
C4—H4B | 0.9700 | C21—C22 | 1.376 (10) |
C5—C6 | 1.488 (13) | C21—C26 | 1.383 (10) |
C5—H5A | 0.9700 | C22—C23 | 1.365 (12) |
C5—H5B | 0.9700 | C22—H22 | 0.9300 |
C6—H6A | 0.9700 | C23—C24 | 1.395 (12) |
C6—H6B | 0.9700 | C23—H23 | 0.9300 |
C7—C8 | 1.516 (11) | C24—C25 | 1.367 (12) |
C7—H7A | 0.9700 | C24—H24 | 0.9300 |
C7—H7B | 0.9700 | C25—C26 | 1.373 (10) |
C8—H8A | 0.9700 | C25—H25 | 0.9300 |
C8—H8B | 0.9700 | | |
| | | |
N1—Hg1—N2 | 158.2 (2) | C8—C7—H7B | 109.1 |
N1—Hg1—O4 | 120.61 (19) | H7A—C7—H7B | 107.8 |
N2—Hg1—O4 | 75.49 (19) | O4—C8—C7 | 106.5 (6) |
N1—Hg1—O5 | 108.9 (2) | O4—C8—H8A | 110.4 |
N2—Hg1—O5 | 76.2 (2) | C7—C8—H8A | 110.4 |
O4—Hg1—O5 | 108.0 (2) | O4—C8—H8B | 110.4 |
N1—Hg1—O1 | 72.9 (2) | C7—C8—H8B | 110.4 |
N2—Hg1—O1 | 128.7 (2) | H8A—C8—H8B | 108.6 |
O4—Hg1—O1 | 69.0 (2) | C10—C9—N2 | 114.1 (6) |
O5—Hg1—O1 | 80.9 (2) | C10—C9—H9A | 108.7 |
N1—Hg1—O3 | 73.5 (2) | N2—C9—H9A | 108.7 |
N2—Hg1—O3 | 96.75 (19) | C10—C9—H9B | 108.7 |
O4—Hg1—O3 | 80.8 (2) | N2—C9—H9B | 108.7 |
O5—Hg1—O3 | 166.47 (19) | H9A—C9—H9B | 107.6 |
O1—Hg1—O3 | 112.2 (2) | O5—C10—C9 | 108.4 (7) |
N1—Hg1—O2 | 73.05 (18) | O5—C10—H10A | 110.0 |
N2—Hg1—O2 | 87.82 (18) | C9—C10—H10A | 110.0 |
O4—Hg1—O2 | 159.80 (18) | O5—C10—H10B | 110.0 |
O5—Hg1—O2 | 78.23 (19) | C9—C10—H10B | 110.0 |
O1—Hg1—O2 | 131.2 (2) | H10A—C10—H10B | 108.4 |
O3—Hg1—O2 | 90.11 (18) | C12—C11—N2 | 117.2 (6) |
C2—O1—Hg1 | 109.4 (5) | C12—C11—H11A | 108.0 |
C2—O1—H1 | 109.2 | N2—C11—H11A | 108.0 |
Hg1—O1—H1 | 126.6 | C12—C11—H11B | 108.0 |
C4—O2—Hg1 | 95.6 (4) | N2—C11—H11B | 108.0 |
C4—O2—H2 | 109.3 | H11A—C11—H11B | 107.3 |
Hg1—O2—H2 | 119.1 | O6—C12—C11 | 111.9 (7) |
C6—O3—Hg1 | 106.8 (5) | O6—C12—H12A | 109.2 |
C6—O3—H3 | 109.1 | C11—C12—H12A | 109.2 |
Hg1—O3—H3 | 130.1 | O6—C12—H12B | 109.2 |
C8—O4—Hg1 | 103.6 (4) | C11—C12—H12B | 109.2 |
C8—O4—H4 | 109.3 | H12A—C12—H12B | 107.9 |
Hg1—O4—H4 | 116.7 | O8—S1—O9 | 115.2 (4) |
C10—O5—Hg1 | 104.7 (4) | O8—S1—N3 | 110.4 (4) |
C10—O5—H5 | 109.3 | O9—S1—N3 | 111.8 (4) |
Hg1—O5—H5 | 110.9 | O8—S1—C19 | 109.2 (4) |
C12—O6—H6 | 109.3 | O9—S1—C19 | 112.1 (4) |
C5—N1—C3 | 112.6 (7) | N3—S1—C19 | 96.7 (3) |
C5—N1—C1 | 109.6 (7) | C13—N3—S1 | 111.7 (5) |
C3—N1—C1 | 106.3 (7) | O7—C13—N3 | 123.3 (7) |
C5—N1—Hg1 | 108.2 (5) | O7—C13—C14 | 123.8 (7) |
C3—N1—Hg1 | 111.3 (5) | N3—C13—C14 | 112.9 (6) |
C1—N1—Hg1 | 108.8 (5) | C19—C14—C15 | 120.7 (7) |
C7—N2—C9 | 110.5 (6) | C19—C14—C13 | 110.8 (6) |
C7—N2—C11 | 112.0 (5) | C15—C14—C13 | 128.5 (7) |
C9—N2—C11 | 110.5 (5) | C16—C15—C14 | 118.0 (7) |
C7—N2—Hg1 | 109.8 (4) | C16—C15—H15 | 121.0 |
C9—N2—Hg1 | 107.9 (4) | C14—C15—H15 | 121.0 |
C11—N2—Hg1 | 105.9 (4) | C15—C16—C17 | 121.1 (7) |
C2—C1—N1 | 117.9 (8) | C15—C16—H16 | 119.5 |
C2—C1—H1A | 107.8 | C17—C16—H16 | 119.5 |
N1—C1—H1A | 107.8 | C18—C17—C16 | 120.6 (8) |
C2—C1—H1B | 107.8 | C18—C17—H17 | 119.7 |
N1—C1—H1B | 107.8 | C16—C17—H17 | 119.7 |
H1A—C1—H1B | 107.2 | C17—C18—C19 | 117.2 (7) |
O1—C2—C1 | 113.2 (8) | C17—C18—H18 | 121.4 |
O1—C2—H2A | 108.9 | C19—C18—H18 | 121.4 |
C1—C2—H2A | 108.9 | C14—C19—C18 | 122.3 (7) |
O1—C2—H2B | 108.9 | C14—C19—S1 | 107.8 (5) |
C1—C2—H2B | 108.9 | C18—C19—S1 | 129.9 (6) |
H2A—C2—H2B | 107.7 | O12—S2—O11 | 114.9 (4) |
C4—C3—N1 | 118.0 (7) | O12—S2—N4 | 111.7 (4) |
C4—C3—H3A | 107.8 | O11—S2—N4 | 110.3 (4) |
N1—C3—H3A | 107.8 | O12—S2—C26 | 111.7 (4) |
C4—C3—H3B | 107.8 | O11—S2—C26 | 109.8 (4) |
N1—C3—H3B | 107.8 | N4—S2—C26 | 97.0 (3) |
H3A—C3—H3B | 107.1 | C20—N4—S2 | 111.5 (5) |
O2—C4—C3 | 109.6 (7) | O10—C20—N4 | 123.0 (7) |
O2—C4—H4A | 109.7 | O10—C20—C21 | 123.7 (6) |
C3—C4—H4A | 109.7 | N4—C20—C21 | 113.3 (6) |
O2—C4—H4B | 109.7 | C22—C21—C26 | 119.7 (7) |
C3—C4—H4B | 109.7 | C22—C21—C20 | 129.1 (7) |
H4A—C4—H4B | 108.2 | C26—C21—C20 | 111.1 (6) |
N1—C5—C6 | 116.8 (8) | C23—C22—C21 | 118.9 (7) |
N1—C5—H5A | 108.1 | C23—C22—H22 | 120.5 |
C6—C5—H5A | 108.1 | C21—C22—H22 | 120.5 |
N1—C5—H5B | 108.1 | C22—C23—C24 | 120.8 (7) |
C6—C5—H5B | 108.1 | C22—C23—H23 | 119.6 |
H5A—C5—H5B | 107.3 | C24—C23—H23 | 119.6 |
O3—C6—C5 | 112.2 (8) | C25—C24—C23 | 120.7 (8) |
O3—C6—H6A | 109.2 | C25—C24—H24 | 119.6 |
C5—C6—H6A | 109.2 | C23—C24—H24 | 119.6 |
O3—C6—H6B | 109.2 | C24—C25—C26 | 117.8 (7) |
C5—C6—H6B | 109.2 | C24—C25—H25 | 121.1 |
H6A—C6—H6B | 107.9 | C26—C25—H25 | 121.1 |
N2—C7—C8 | 112.7 (6) | C25—C26—C21 | 122.0 (7) |
N2—C7—H7A | 109.1 | C25—C26—S2 | 130.8 (6) |
C8—C7—H7A | 109.1 | C21—C26—S2 | 107.2 (5) |
N2—C7—H7B | 109.1 | | |
| | | |
N1—Hg1—O1—C2 | −5.5 (7) | Hg1—O2—C4—C3 | −54.7 (7) |
N2—Hg1—O1—C2 | 171.6 (6) | N1—C3—C4—O2 | 65.9 (12) |
O4—Hg1—O1—C2 | −139.1 (8) | C3—N1—C5—C6 | 70.0 (11) |
O5—Hg1—O1—C2 | 107.6 (7) | C1—N1—C5—C6 | −171.9 (8) |
O3—Hg1—O1—C2 | −69.1 (7) | Hg1—N1—C5—C6 | −53.4 (10) |
O2—Hg1—O1—C2 | 42.0 (8) | Hg1—O3—C6—C5 | −22.2 (10) |
N1—Hg1—O2—C4 | 31.4 (5) | N1—C5—C6—O3 | 52.4 (12) |
N2—Hg1—O2—C4 | −159.2 (5) | C9—N2—C7—C8 | 156.5 (6) |
O4—Hg1—O2—C4 | 166.9 (5) | C11—N2—C7—C8 | −79.8 (7) |
O5—Hg1—O2—C4 | −82.8 (5) | Hg1—N2—C7—C8 | 37.6 (7) |
O1—Hg1—O2—C4 | −16.2 (6) | Hg1—O4—C8—C7 | 52.2 (6) |
O3—Hg1—O2—C4 | 104.1 (5) | N2—C7—C8—O4 | −64.4 (8) |
N1—Hg1—O3—C6 | −2.6 (6) | C7—N2—C9—C10 | −75.3 (8) |
N2—Hg1—O3—C6 | −162.7 (6) | C11—N2—C9—C10 | 160.1 (6) |
O4—Hg1—O3—C6 | 123.2 (6) | Hg1—N2—C9—C10 | 44.8 (7) |
O5—Hg1—O3—C6 | −105.2 (9) | Hg1—O5—C10—C9 | 43.9 (7) |
O1—Hg1—O3—C6 | 60.5 (6) | N2—C9—C10—O5 | −63.6 (9) |
O2—Hg1—O3—C6 | −74.9 (6) | C7—N2—C11—C12 | −81.1 (8) |
N1—Hg1—O4—C8 | 137.8 (5) | C9—N2—C11—C12 | 42.6 (8) |
N2—Hg1—O4—C8 | −26.2 (5) | Hg1—N2—C11—C12 | 159.3 (6) |
O5—Hg1—O4—C8 | −96.1 (5) | N2—C11—C12—O6 | 51.7 (9) |
O1—Hg1—O4—C8 | −168.6 (5) | O8—S1—N3—C13 | 114.7 (6) |
O3—Hg1—O4—C8 | 73.3 (5) | O9—S1—N3—C13 | −115.7 (6) |
O2—Hg1—O4—C8 | 9.0 (8) | C19—S1—N3—C13 | 1.3 (6) |
N1—Hg1—O5—C10 | −174.9 (5) | S1—N3—C13—O7 | −179.2 (7) |
N2—Hg1—O5—C10 | −16.9 (5) | S1—N3—C13—C14 | 0.1 (9) |
O4—Hg1—O5—C10 | 52.5 (5) | O7—C13—C14—C19 | 177.4 (8) |
O1—Hg1—O5—C10 | 116.8 (5) | N3—C13—C14—C19 | −1.8 (9) |
O3—Hg1—O5—C10 | −76.6 (9) | O7—C13—C14—C15 | 0.2 (13) |
O2—Hg1—O5—C10 | −107.6 (5) | N3—C13—C14—C15 | −179.1 (8) |
N2—Hg1—N1—C5 | 92.2 (7) | C19—C14—C15—C16 | 1.0 (12) |
O4—Hg1—N1—C5 | −41.9 (6) | C13—C14—C15—C16 | 178.0 (8) |
O5—Hg1—N1—C5 | −167.5 (5) | C14—C15—C16—C17 | −2.4 (14) |
O1—Hg1—N1—C5 | −93.8 (6) | C15—C16—C17—C18 | 3.2 (16) |
O3—Hg1—N1—C5 | 26.5 (5) | C16—C17—C18—C19 | −2.4 (14) |
O2—Hg1—N1—C5 | 121.7 (5) | C15—C14—C19—C18 | −0.3 (12) |
N2—Hg1—N1—C3 | −31.9 (9) | C13—C14—C19—C18 | −177.8 (7) |
O4—Hg1—N1—C3 | −166.1 (6) | C15—C14—C19—S1 | −179.9 (6) |
O5—Hg1—N1—C3 | 68.3 (6) | C13—C14—C19—S1 | 2.6 (7) |
O1—Hg1—N1—C3 | 142.1 (6) | C17—C18—C19—C14 | 1.1 (12) |
O3—Hg1—N1—C3 | −97.7 (6) | C17—C18—C19—S1 | −179.4 (7) |
O2—Hg1—N1—C3 | −2.4 (6) | O8—S1—C19—C14 | −116.6 (5) |
N2—Hg1—N1—C1 | −148.7 (6) | O9—S1—C19—C14 | 114.4 (6) |
O4—Hg1—N1—C1 | 77.1 (6) | N3—S1—C19—C14 | −2.3 (6) |
O5—Hg1—N1—C1 | −48.5 (6) | O8—S1—C19—C18 | 63.8 (8) |
O1—Hg1—N1—C1 | 25.3 (6) | O9—S1—C19—C18 | −65.1 (9) |
O3—Hg1—N1—C1 | 145.5 (6) | N3—S1—C19—C18 | 178.1 (8) |
O2—Hg1—N1—C1 | −119.2 (6) | O12—S2—N4—C20 | −117.0 (6) |
N1—Hg1—N2—C7 | −146.3 (6) | O11—S2—N4—C20 | 113.9 (6) |
O4—Hg1—N2—C7 | −5.9 (4) | C26—S2—N4—C20 | −0.3 (7) |
O5—Hg1—N2—C7 | 107.2 (5) | S2—N4—C20—O10 | −179.4 (7) |
O1—Hg1—N2—C7 | 41.0 (6) | S2—N4—C20—C21 | 0.7 (9) |
O3—Hg1—N2—C7 | −84.6 (5) | O10—C20—C21—C22 | 3.7 (14) |
O2—Hg1—N2—C7 | −174.4 (5) | N4—C20—C21—C22 | −176.4 (8) |
N1—Hg1—N2—C9 | 93.2 (7) | O10—C20—C21—C26 | 179.3 (8) |
O4—Hg1—N2—C9 | −126.4 (5) | N4—C20—C21—C26 | −0.8 (10) |
O5—Hg1—N2—C9 | −13.3 (4) | C26—C21—C22—C23 | 0.4 (13) |
O1—Hg1—N2—C9 | −79.4 (5) | C20—C21—C22—C23 | 175.6 (8) |
O3—Hg1—N2—C9 | 154.9 (4) | C21—C22—C23—C24 | 0.3 (15) |
O2—Hg1—N2—C9 | 65.1 (4) | C22—C23—C24—C25 | 0.0 (15) |
N1—Hg1—N2—C11 | −25.2 (8) | C23—C24—C25—C26 | −1.0 (14) |
O4—Hg1—N2—C11 | 115.2 (4) | C24—C25—C26—C21 | 1.8 (12) |
O5—Hg1—N2—C11 | −131.7 (4) | C24—C25—C26—S2 | −175.8 (7) |
O1—Hg1—N2—C11 | 162.2 (4) | C22—C21—C26—C25 | −1.5 (12) |
O3—Hg1—N2—C11 | 36.5 (4) | C20—C21—C26—C25 | −177.5 (7) |
O2—Hg1—N2—C11 | −53.3 (4) | C22—C21—C26—S2 | 176.6 (6) |
C5—N1—C1—C2 | 69.5 (11) | C20—C21—C26—S2 | 0.6 (8) |
C3—N1—C1—C2 | −168.6 (9) | O12—S2—C26—C25 | −65.7 (9) |
Hg1—N1—C1—C2 | −48.6 (10) | O11—S2—C26—C25 | 63.1 (9) |
Hg1—O1—C2—C1 | −16.9 (11) | N4—S2—C26—C25 | 177.6 (8) |
N1—C1—C2—O1 | 44.6 (13) | O12—S2—C26—C21 | 116.5 (6) |
C5—N1—C3—C4 | −150.4 (9) | O11—S2—C26—C21 | −114.7 (6) |
C1—N1—C3—C4 | 89.5 (10) | N4—S2—C26—C21 | −0.2 (6) |
Hg1—N1—C3—C4 | −28.8 (11) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O7i | 0.84 | 2.24 | 2.951 (10) | 143 |
O2—H2···N4 | 0.86 | 1.92 | 2.775 (8) | 177 |
O3—H3···O7ii | 0.85 | 1.91 | 2.754 (8) | 172 |
O4—H4···N3i | 0.85 | 1.97 | 2.806 (8) | 164 |
O5—H5···O10iii | 0.86 | 1.80 | 2.650 (8) | 167 |
O6—H6···O8 | 0.86 | 2.00 | 2.813 (8) | 159 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x, −y, −z; (iii) x, y, z+1. |
Experimental details
| (I) | (II) |
Crystal data |
Chemical formula | [Cd(C6H15NO3)2]2C7H4NO3S | [Hg(C6H15NO3)2]2C7H4NO3S |
Mr | 775.12 | 863.31 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 293 | 293 |
a, b, c (Å) | 13.2825 (9), 14.9093 (11), 8.9376 (10) | 12.588 (2), 15.934 (3), 7.9944 (14) |
α, β, γ (°) | 98.002 (8), 102.662 (8), 63.762 (5) | 91.791 (14), 91.343 (14), 72.965 (13) |
V (Å3) | 1547.2 (2) | 1532.2 (4) |
Z | 2 | 2 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.91 | 5.23 |
Crystal size (mm) | 0.4 × 0.2 × 0.2 | 0.50 × 0.35 × 0.10 |
|
Data collection |
Diffractometer | Rigaku AFC-7S diffractometer | Rigaku AFC-7S diffractometer |
Absorption correction | ψ-scan (North et al., 1968) | ψ-scan (North et al., 1968) |
Tmin, Tmax | 0.797, 0.834 | 0.113, 0.593 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12760, 11203, 7948 | 11526, 11091, 5241 |
Rint | 0.025 | 0.042 |
(sin θ/λ)max (Å−1) | 0.756 | 0.756 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.115, 1.02 | 0.050, 0.159, 0.99 |
No. of reflections | 11203 | 11091 |
No. of parameters | 478 | 412 |
No. of restraints | 145 | 0 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.80, −0.87 | 1.94, −3.76 |
Selected geometric parameters (Å, º) for (I) topCd1—O4 | 2.3274 (19) | Cd1—O2 | 2.3862 (19) |
Cd1—O5 | 2.3464 (19) | Cd1—N1 | 2.392 (2) |
Cd1—O1 | 2.3676 (19) | Cd1—O3 | 2.415 (2) |
Cd1—N2 | 2.375 (2) | | |
| | | |
O4—Cd1—O5 | 102.28 (8) | O5—Cd1—N1 | 125.92 (7) |
O4—Cd1—O1 | 81.81 (7) | O1—Cd1—N1 | 72.11 (7) |
O5—Cd1—O1 | 72.95 (7) | N2—Cd1—N1 | 154.11 (7) |
O4—Cd1—N2 | 74.86 (7) | O2—Cd1—N1 | 73.97 (8) |
O5—Cd1—N2 | 73.64 (7) | O4—Cd1—O3 | 80.07 (8) |
O1—Cd1—N2 | 133.59 (7) | O5—Cd1—O3 | 158.08 (7) |
O4—Cd1—O2 | 166.01 (7) | O1—Cd1—O3 | 128.66 (7) |
O5—Cd1—O2 | 82.73 (8) | N2—Cd1—O3 | 86.21 (7) |
O1—Cd1—O2 | 112.18 (7) | O2—Cd1—O3 | 90.46 (8) |
N2—Cd1—O2 | 94.39 (7) | N1—Cd1—O3 | 71.15 (7) |
O4—Cd1—N1 | 111.99 (8) | | |
Hydrogen-bond geometry (Å, º) for (I) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O10 | 0.86 | 1.90 | 2.749 (3) | 171 |
O2—H2···O7i | 0.86 | 1.83 | 2.679 (3) | 173 |
O3—H3···N3ii | 0.86 | 1.95 | 2.804 (3) | 178 |
O4—H4···O10iii | 0.86 | 1.86 | 2.715 (3) | 175 |
O5—H5···N4 | 0.86 | 1.86 | 2.714 (3) | 172 |
O6A—H6A···O9 | 0.88 | 1.97 | 2.778 (15) | 152 |
O6B—H6B···O9 | 0.88 | 1.93 | 2.78 (2) | 162 |
Symmetry codes: (i) −x, −y, −z−1; (ii) x, y, z+1; (iii) −x, −y+1, −z+1. |
Selected geometric parameters (Å, º) for (II) topHg1—N1 | 2.234 (5) | Hg1—O3 | 2.618 (5) |
Hg1—N2 | 2.239 (5) | Hg1—O4 | 2.468 (5) |
Hg1—O1 | 2.581 (7) | Hg1—O5 | 2.497 (6) |
Hg1—O2 | 2.730 (5) | | |
| | | |
N1—Hg1—N2 | 158.2 (2) | N2—Hg1—O3 | 96.75 (19) |
N1—Hg1—O4 | 120.61 (19) | O4—Hg1—O3 | 80.8 (2) |
N2—Hg1—O4 | 75.49 (19) | O5—Hg1—O3 | 166.47 (19) |
N1—Hg1—O5 | 108.9 (2) | O1—Hg1—O3 | 112.2 (2) |
N2—Hg1—O5 | 76.2 (2) | N1—Hg1—O2 | 73.05 (18) |
O4—Hg1—O5 | 108.0 (2) | N2—Hg1—O2 | 87.82 (18) |
N1—Hg1—O1 | 72.9 (2) | O4—Hg1—O2 | 159.80 (18) |
N2—Hg1—O1 | 128.7 (2) | O5—Hg1—O2 | 78.23 (19) |
O4—Hg1—O1 | 69.0 (2) | O1—Hg1—O2 | 131.2 (2) |
O5—Hg1—O1 | 80.9 (2) | O3—Hg1—O2 | 90.11 (18) |
N1—Hg1—O3 | 73.5 (2) | | |
Hydrogen-bond geometry (Å, º) for (II) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O7i | 0.84 | 2.24 | 2.951 (10) | 143 |
O2—H2···N4 | 0.86 | 1.92 | 2.775 (8) | 177 |
O3—H3···O7ii | 0.85 | 1.91 | 2.754 (8) | 172 |
O4—H4···N3i | 0.85 | 1.97 | 2.806 (8) | 164 |
O5—H5···O10iii | 0.86 | 1.80 | 2.650 (8) | 167 |
O6—H6···O8 | 0.86 | 2.00 | 2.813 (8) | 159 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x, −y, −z; (iii) x, y, z+1. |
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Triethanolamine (tea) is an amino alcohol used in a number of commercial applications such as herbicides, surface-active agents, corrosion inhibitors and cement additives (Esker et al., 1999). Because of its double action as both a tertiary amine and a primary alcohol, tea readily coordinates to metal ions to form complexes and also stabilizes the anions by hydrogen bonding (Sen & Dotson, 1970; Brannon et al., 1971; Bajaj & Poonia, 1988). As part of our research effort on the preparation and spectral, thermal and structural characterization of transition metal complexes of tea (Icbudak et al., 1995; Yilmaz et al., 1997; Topcu et al., 2001a), we here report the structural characterization of the rather unusual seven-coordinate title compounds, (I) and (II). \sch
The aim of the present work was to prepare a series of mixed-ligand complexes containing both tea and sac ligands. However, it was observed that the bulky and polydentate tea ligand coordinates to the metal ions completely and does not leave any site available for the coordination of sac (Topcu et al., 2001b). Therefore, the sac ions are present as counterions in metal complexes with tea.
The structures of [Cd(tea)2](sac)2, (I), and [Hg(tea)2](sac)2, (II), are shown in Figs. 1 and 2, respectively. Tables 1 to 4 list their bond and hydrogen-bonding geometries. The structures resemble each other and consist of a complex cation and two sac ions. In the complex cation, two neutral tea ligands coordinate to the CdII or HgII ions. The two tea ligands exhibit different coordination modes in the same coordination polyhedron. One of them is coordinated to the central metal ion, acting as a tetradentate ligand using all donor atoms, i.e. the amino N atom and all three hydroxyl O atoms, while the other is bonded to the metal ion tridentately through its N atom and two hydroxyl O atoms, one hydroxyl O atom of the ethanolic groups being non-coordinated. A similar inequivalency of two tea ligands coordinated to the MnII ion in a distorted pentagonal bipyramidal geometry has been reported for the [Mn(tea)2](CF3COO)2 complex (Andruh et al., 1993). A coordination polyhedron containing the same ligand with two different coordination modes was also reported for the monoethanolamine complex with the CuII ion (Bombicz et al., 1997).
The tri- and tetradentate coordinations of the two tea ligands result in a relatively rare coordination number of seven for CdII and an unusual example for HgII, since CdII and HgII usually possess octahedral as well as tetrahedral geometry (Holloway & Melnik, 1995). Although eight-coordinate SrII (Naiini et al., 1995; Poonia et al., 1999) and YIII (Naiini et al., 1995) complexes containing two tetradentate tea ligands have recently been reported, only one CdII complex with eight-coordination, [Cd(tea)2](NO3)2, has been reported in the literature to date (Naiini et al., 1995). It should be noted that the tea complexes of CdII reported in this paper and in the literature have different coordination numbers and geometries. This may be attributed to the presence of different counterions such as nitrate or saccharinate.
The seven-coordination geometry around the CdII and HgII ions in (I) and (II) is described as a monocapped trigonal prism (C2v). Dihedral angles between the least-squares planes are as follows: 53.2 (1) and 46.0 (1)° between O2—O3—O4—O5 (plane 1) and O2—N1—O1—O5 (plane 2), 50.8 (1) and 51.2 (1)° between O3—O4—O1—N1 (plane 3) and plane 1, and 76.0 (1) and 82.9 (2)° between planes 2 and 3 for (I) and (II), respectively. The dihedral angle between two triangular planes, O2—O3—N1 and O5—O4—O1, is only 8.5 (1)° for (I) and 12.4 (4)° for (II). Dihedral angles between these triangular and square planes are in the range of 83.6 (1)–87.5 (1)° for (I) and 73.6 (2)–85.9 (2)° for (II). The central CdII and HgII ions are located 0.362 (1) and 0.378 (1) Å from the least-squares plane O2—O3—O4—O5, respectively.
All ethylene C atoms (C1—C6) of the tetradentately coordinated tea ligand and the free hydroxyl O atom (O6) of the tridentate tea ligand in (I) are noticeably disordered over two positions, with occupancies of 30 (1)% and 70 (1)% for the C atoms, and 56 (1)% and 44 (1)% for atom O6. In addition, atom O1 in (II) is slightly disordered and, therefore, the disorder was not resolved.
The M—N bond distances are 2.375 (2) and 2.392 (2) Å for (I), and 2.234 (5) and 2.239 (5) Å for (II). The M—O bonds are in the range 2.327 (2)–2.415 (2) Å for (I) and 2.468 (5)–2.730 (5) Å for (II). The bond lengths in (I) are somewhat shorter than those of the eight-coordinate CdII complex with tea (Naiini et al., 1995).
Both sac ions are essentially planar, with r.m.s. deviations of 0.0057 and 0.0292 Å in (I), and 0.023 and 0.024 Å in (II). In both complexes, the sac ions adopt a parallel alignment, and the dihedral angles between the corresponding planes are 3.5 (1) and 1.1 (1)° for (I) and (II), respectively. Thus, the phenyl rings approximately superimpose on each other and are connected by weak π–π interactions of 4.166 (1) Å in (I), and 4.038 (1) Å in (II).
The crystals of the two complexes feature numerous hydrogen bonds (Figs. 3 and 4). The H atoms of the free and coordinated hydroxyl H atoms of the tea ligands are involved in intermolecular hydrogen bonding with the negatively charged amine N atoms and the carbonyl and sulfonyl O atoms of neighbouring sac ions. An extensive network of hydrogen bonds and other intermolecular interactions maintains the crystal structure by forming an infinite three-dimensional lattice.