metal-organic compounds
μ-Sulfido-bis{[1,1′-bis(diphenylphosphanyl)ferrocene-κ2P,P′]gold} methanol monosolvate
aDepartment of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan
*Correspondence e-mail: kojimat15@chem.sci.osaka-u.ac.jp
The gold complex in title compound, [Au2Fe(C17H14P)2S]·CH3OH, (I)·CH3OH, is closely similar to the previously reported (I)·2CHCl3, reported in the literature [Canales et al. (1996). J. Am. Chem. Soc. 118, 4839–4845]. Both crystallize in the monoclinic crystal systems but the space groups differ, P21/n for (I)·CH3OH compared to P2/n for (I)·2CHCl3. The two structures can be considered as polymorphs due to solvation differences. In (I)·CH3OH, all atoms of the methanol solvent molecule are disordered over two sets of sites with an occupancy ratio of 0.822 (12):0.178 (12). The features O—H⋯S, C—H⋯S hydrogen bonds and C—H⋯π interactions that stack the complex molecules along the a-axis direction.
Keywords: crystal structure; digold(I) molecule; pseudopolymorph; hydrogen bonding; C—H⋯π interactions.
CCDC reference: 1444737
Structure description
The 2(dppf)(S)] complex molecule, (I)·CH3OH, dppf = 1,1′-bis(diphenylphosphino)ferrocene) and a methanol solvate molecule, all atoms of which are disordered over two sets of sites with a 0.822 (12):0.178 (12) occupancy ratio, Fig. 1. Both AuI cations adopt a slightly distorted linear coordination geometry, each binding separate P atoms from the dppf ligand and bridged by the sulfido anion, leading to a close intramolecular Au—Au contact of 2.8857 (3) Å, similar to that observed in the closely related (I)·2CHCl3 (Canales et al., 1996). The Au—S and Au—P distances, Table 1, are also similar to those in the earlier report. The space groups of these two structures differ, P21/n for (I)·CH3OH and P2/n for (I)·2CHCl3. The two structures can be considered as polymorphs due to solvation differences which will significantly affect the crystal packing. Apart from the polymorph, only two examples of digoldsufide systems similarly bridged by bidentate diphenylphosphino ligands, (μ2-2,5-bis(diphenylphosphinomethyl)thiophene)(μ2-sulfido)digold(I) (Chen et al., 1998) and {μ2-1,4-bis[(di;phenylphosphino)methyl]benzene}(μ2-sulfido)digold(I) chloroform solvate (Hofreiter et al., 1995) are found in the Cambridge Structural Database (Groom & Allen, 2014).
in the title contains one [Au
|
In the . A C—H⋯S hydrogen bond and two edge-to-face C—H⋯π contacts link adjacent complex molecules, stacking them along the a-axis direction, Fig. 2. For the polymorphic structure, which lies about a twofold rotation axis, C—H⋯S and C—H⋯Cl hydrogen bonds, a weaker C—H⋯π contact and an intermolecular Cl⋯Cl halogen bond stabilize the structure.
an O—H⋯S hydrogen bond links the major disorder component of the methanol molecule to the complex molecule in the Table 2Synthesis and crystallization
To a solution of [1,1′-bis(diphenylphosphino)ferrocene]bis(D-penicillaminato)digold (15.0 mg, 15.8 mmol) in 3 ml of methanol was added 20 µL (0.02 mmol) of an aqueous sodium hydrogen sulfide solution (1 M). The solution was allowed to stand at room temperature for 1 h when small quantities of yellow needle-like crystals of [Au2(C34H28FeP2)(S)]·CH3OH were obtained.
Refinement
Crystal data, data collection and structure . All atoms of the methanol solvate molecules were disordered over two sets ofsites. Their occupancies were refined to sum to unity and converged at 0.822 (12) and 0.178 (12), respectively. Ten reflections below θmin = 3.227, with Fo <<< Fc were omitted as they were likely to have been obscured by the beamstop.
details are summarized in Table 3Structural data
CCDC reference: 1444737
10.1107/S241431461502492X/sj4004sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S241431461502492X/sj4004Isup2.hkl
To a solution of (1,1'-bis(diphenylphosphino)ferrocene)digold) (15.0 mg, 15.8 mmol) in 3 ml of methanol was added 20 µL (0.02 mmol) of an aqueous sodium hydrogen sulfide solution (1 M). The solution was allowed to stand at room temperature for 1 h when small quantities of yellow needle-like crystals of [Au2(C34H28FeP2)(S)]·CH3OH were obtained.
Crystal data, data collection and structure
details are summarized in Table 1. A l l atoms of the methanol solvate molecules were disordered over two sites. Their occupancies were refined to sum to unity and converged at 0.822 (12) and 0.178 (12) respectively. Ten reflections below theta min = 3.227, with Fo <<< Fc were omitted as they were likely to have been obscured by the beamstop.To a solution of {1,1'-bis[diphenylphosphino)ferrocene]digold} (15.0 mg, 15.8 mmol) in 3 ml of methanol was added 20 µL (0.02 mmol) of an aqueous sodium hydrogen sulfide solution (1 M). The solution was allowed to stand at room temperature for 1 h when small quantities of yellow needle-like crystals of [Au2(C34H28FeP2)(S)]·CH3OH were obtained.
Crystal data, data collection and structure θmin = 3.227, with Fo <<< Fc were omitted as they were likely to have been obscured by the beamstop.
details are summarized in Table 3. A l l atoms of the methanol solvate molecules were disordered over two sets ofsites. Their occupancies were refined to sum to unity and converged at 0.822 (12) and 0.178 (12) respectively. Ten reflections belowThe
in the title contains one [Au2(dppf)(S)] complex molecule, (I)·CH3OH, dppf = 1,1'-bis(diphenylphosphino)ferrocene) and a methanol solvate molecule, all atoms of which are disordered over two sets of sites with a 0.822 (12):0.178 (12) occupancy ratio, Fig. 1. Both AuI cations adopt a slightly distorted linear coordination geometry, each binding separate P atoms from the dppf ligand and bridged by the sulfido anion, leading to a close intramolecular Au—Au contact of 2.8857 (3) Å, similar to that observed in the closely related (I)·2CHCl3 (Canales et al., 1996). The Au—S and Au—P distances, Table 1, are also similar to those in the earlier report. Although the space groups of these two structures differ, P21/n for (I)·CH3OH and P2/n for (I)·2CHCl3. The two structures can be considered as pseudopolymorphs due to solvation differences which will significantly affect the crystal packing. Apart from the psudopolymorph, only two examples of digoldsufide systems similarly bridged by bidentate diphenylphosphino ligands, (µ2-2,5-bis(diphenylphosphinomethyl)thiophene)(µ2-sulfido)digold(I) (Chen et al., 1998) and {µ2-1,4-bis[(diphenylphosphino)methyl]benzene}(µ2-sulfido)digold(I) chloroform solvate (Hofreiter et al., 1995) are found in the Cambridge Structural Database, (Groom & Allen, 2014).In the π contacts link adjacent complex molecules, stacking them along the a-axis direction, Fig. 2. For the psudopolymorphic structure, which lies about a twofold rotation axis, C—H···S and C—H···Cl hydrogen bonds, a weaker C—H···π contact and an intermolecular Cl···Cl halogen bond stabilize the structure.
an O—H···S hydrogen bond links the major disorder component of the methanol molecule to the complex molecule in the Table 2. A C—H···S hydrogen bond and two edge-to-face C—H···Data collection: PROCESS-AUTO (Rigaku, 2000); cell
PROCESS-AUTO (Rigaku, 2000); data reduction: PROCESS-AUTO (Rigaku, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Putz & Brandenburg, 2011); software used to prepare material for publication: WinGX (Farrugia, 2012).Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are drawn as spheres of arbitrary radii. | |
Fig. 2. Overall packing for the title compound viewed along the a axis. |
[Au2Fe(C17H14P)2S]·CH4O | F(000) = 1920 |
Mr = 1012.39 | Dx = 2.087 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71075 Å |
a = 13.7434 (13) Å | Cell parameters from 8771 reflections |
b = 12.6277 (13) Å | θ = 3.0–27.5° |
c = 18.7630 (18) Å | µ = 9.72 mm−1 |
β = 98.352 (7)° | T = 200 K |
V = 3221.7 (5) Å3 | Needle, yellow |
Z = 4 | 0.30 × 0.10 × 0.01 mm |
Rigaku VariMax RAPID diffractometer | 5445 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.045 |
ω scans | θmax = 25.7°, θmin = 3.2° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −16→16 |
Tmin = 0.572, Tmax = 0.995 | k = −15→15 |
26469 measured reflections | l = −22→22 |
6105 independent reflections |
Refinement on F2 | 8 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.052 | w = 1/[σ2(Fo2) + (0.0208P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max = 0.001 |
6105 reflections | Δρmax = 1.03 e Å−3 |
392 parameters | Δρmin = −0.55 e Å−3 |
[Au2Fe(C17H14P)2S]·CH4O | V = 3221.7 (5) Å3 |
Mr = 1012.39 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.7434 (13) Å | µ = 9.72 mm−1 |
b = 12.6277 (13) Å | T = 200 K |
c = 18.7630 (18) Å | 0.30 × 0.10 × 0.01 mm |
β = 98.352 (7)° |
Rigaku VariMax RAPID diffractometer | 6105 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 5445 reflections with I > 2σ(I) |
Tmin = 0.572, Tmax = 0.995 | Rint = 0.045 |
26469 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 8 restraints |
wR(F2) = 0.052 | H-atom parameters constrained |
S = 1.13 | Δρmax = 1.03 e Å−3 |
6105 reflections | Δρmin = −0.55 e Å−3 |
392 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 | Occ. (<1) | |
Au1 | 0.39803 (2) | 0.23503 (2) | 0.09507 (2) | 0.02544 (6) | |
Au2 | 0.23078 (2) | 0.20488 (2) | 0.16975 (2) | 0.02555 (6) | |
Fe1 | 0.47576 (5) | 0.32726 (5) | 0.31861 (3) | 0.02381 (15) | |
P1 | 0.54820 (9) | 0.27998 (9) | 0.15170 (6) | 0.0231 (3) | |
P2 | 0.23049 (9) | 0.25682 (9) | 0.28416 (6) | 0.0235 (3) | |
S1 | 0.24432 (9) | 0.17001 (10) | 0.05135 (6) | 0.0315 (3) | |
C1 | 0.5572 (3) | 0.2623 (3) | 0.2479 (2) | 0.0226 (10) | |
C2 | 0.6197 (3) | 0.3142 (4) | 0.3044 (2) | 0.0274 (10) | |
H2 | 0.6635 | 0.3708 | 0.2989 | 0.033* | |
C3 | 0.6049 (4) | 0.2665 (4) | 0.3704 (3) | 0.0308 (11) | |
H3 | 0.6367 | 0.2859 | 0.4170 | 0.037* | |
C4 | 0.5348 (3) | 0.1852 (4) | 0.3546 (3) | 0.0320 (11) | |
H4 | 0.5112 | 0.1404 | 0.3890 | 0.038* | |
C5 | 0.5054 (3) | 0.1814 (3) | 0.2799 (2) | 0.0260 (10) | |
H5 | 0.4592 | 0.1334 | 0.2550 | 0.031* | |
C6 | 0.5925 (3) | 0.4134 (3) | 0.1388 (2) | 0.0265 (10) | |
C7 | 0.5275 (4) | 0.4882 (4) | 0.1072 (3) | 0.0432 (14) | |
H7 | 0.4600 | 0.4709 | 0.0944 | 0.052* | |
C8 | 0.5609 (5) | 0.5893 (4) | 0.0940 (4) | 0.0604 (18) | |
H8 | 0.5159 | 0.6404 | 0.0713 | 0.073* | |
C9 | 0.6571 (5) | 0.6162 (4) | 0.1131 (3) | 0.0498 (15) | |
H9 | 0.6789 | 0.6857 | 0.1043 | 0.060* | |
C10 | 0.7220 (4) | 0.5426 (4) | 0.1448 (3) | 0.0403 (13) | |
H10 | 0.7891 | 0.5613 | 0.1586 | 0.048* | |
C11 | 0.6908 (3) | 0.4405 (4) | 0.1572 (2) | 0.0321 (11) | |
H11 | 0.7368 | 0.3892 | 0.1783 | 0.038* | |
C12 | 0.6439 (3) | 0.1923 (3) | 0.1277 (2) | 0.0246 (10) | |
C13 | 0.7252 (3) | 0.1646 (4) | 0.1775 (3) | 0.0316 (11) | |
H13 | 0.7322 | 0.1926 | 0.2249 | 0.038* | |
C14 | 0.7960 (4) | 0.0964 (4) | 0.1582 (3) | 0.0402 (13) | |
H14 | 0.8520 | 0.0788 | 0.1921 | 0.048* | |
C15 | 0.7848 (4) | 0.0543 (4) | 0.0900 (3) | 0.0408 (13) | |
H15 | 0.8333 | 0.0075 | 0.0767 | 0.049* | |
C16 | 0.7043 (4) | 0.0793 (4) | 0.0407 (3) | 0.0423 (14) | |
H16 | 0.6968 | 0.0492 | −0.0061 | 0.051* | |
C17 | 0.6335 (4) | 0.1488 (3) | 0.0594 (2) | 0.0311 (11) | |
H17 | 0.5779 | 0.1664 | 0.0251 | 0.037* | |
C18 | 0.3279 (3) | 0.3494 (3) | 0.3119 (2) | 0.0254 (10) | |
C19 | 0.3748 (3) | 0.3704 (4) | 0.3834 (3) | 0.0334 (12) | |
H19 | 0.3623 | 0.3349 | 0.4257 | 0.040* | |
C20 | 0.4427 (3) | 0.4529 (4) | 0.3803 (3) | 0.0439 (15) | |
H20 | 0.4843 | 0.4826 | 0.4201 | 0.053* | |
C21 | 0.4383 (4) | 0.4837 (4) | 0.3079 (3) | 0.0419 (14) | |
H21 | 0.4763 | 0.5384 | 0.2907 | 0.050* | |
C22 | 0.3681 (3) | 0.4201 (3) | 0.2646 (3) | 0.0320 (12) | |
H22 | 0.3511 | 0.4239 | 0.2138 | 0.038* | |
C23 | 0.2466 (3) | 0.1536 (3) | 0.3525 (2) | 0.0254 (10) | |
C24 | 0.2985 (3) | 0.0625 (4) | 0.3396 (3) | 0.0324 (11) | |
H24 | 0.3234 | 0.0548 | 0.2952 | 0.039* | |
C25 | 0.3141 (4) | −0.0162 (4) | 0.3903 (3) | 0.0410 (13) | |
H25 | 0.3494 | −0.0781 | 0.3809 | 0.049* | |
C26 | 0.2785 (4) | −0.0056 (4) | 0.4547 (3) | 0.0459 (14) | |
H26 | 0.2897 | −0.0602 | 0.4898 | 0.055* | |
C27 | 0.2269 (4) | 0.0834 (4) | 0.4687 (3) | 0.0483 (15) | |
H27 | 0.2020 | 0.0904 | 0.5131 | 0.058* | |
C28 | 0.2115 (4) | 0.1625 (4) | 0.4175 (3) | 0.0363 (12) | |
H28 | 0.1761 | 0.2242 | 0.4272 | 0.044* | |
C29 | 0.1186 (3) | 0.3250 (3) | 0.2995 (2) | 0.0241 (10) | |
C30 | 0.1185 (4) | 0.4138 (4) | 0.3427 (3) | 0.0321 (11) | |
H30 | 0.1791 | 0.4446 | 0.3634 | 0.038* | |
C31 | 0.0309 (4) | 0.4580 (4) | 0.3558 (3) | 0.0408 (13) | |
H31 | 0.0318 | 0.5182 | 0.3863 | 0.049* | |
C32 | −0.0563 (4) | 0.4163 (4) | 0.3254 (3) | 0.0508 (16) | |
H32 | −0.1162 | 0.4474 | 0.3345 | 0.061* | |
C33 | −0.0578 (4) | 0.3285 (4) | 0.2812 (4) | 0.065 (2) | |
H33 | −0.1189 | 0.2990 | 0.2602 | 0.077* | |
C34 | 0.0291 (4) | 0.2838 (4) | 0.2676 (3) | 0.0499 (16) | |
H34 | 0.0278 | 0.2245 | 0.2364 | 0.060* | |
O1 | −0.0057 (4) | 0.1917 (5) | 0.0573 (5) | 0.095 (3) | 0.822 (12) |
H1A | 0.0554 | 0.1950 | 0.0574 | 0.143* | 0.822 (12) |
C35 | −0.0431 (17) | 0.2927 (15) | 0.0602 (13) | 0.113 (7) | 0.822 (12) |
H35A | −0.0284 | 0.3335 | 0.0187 | 0.170* | 0.822 (12) |
H35B | −0.0131 | 0.3273 | 0.1048 | 0.170* | 0.822 (12) |
H35C | −0.1145 | 0.2889 | 0.0593 | 0.170* | 0.822 (12) |
O2 | 0.025 (2) | 0.292 (2) | 0.0241 (16) | 0.074 (11)* | 0.178 (12) |
H2B | 0.0519 | 0.3513 | 0.0309 | 0.111* | 0.178 (12) |
C36 | −0.042 (4) | 0.284 (4) | 0.063 (3) | 0.024 (11)* | 0.178 (12) |
H36A | −0.0388 | 0.3442 | 0.0962 | 0.037* | 0.178 (12) |
H36B | −0.0333 | 0.2179 | 0.0908 | 0.037* | 0.178 (12) |
H36C | −0.1065 | 0.2830 | 0.0326 | 0.037* | 0.178 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Au1 | 0.02336 (10) | 0.03084 (10) | 0.02091 (10) | 0.00051 (8) | −0.00083 (7) | −0.00180 (7) |
Au2 | 0.02393 (10) | 0.02795 (10) | 0.02366 (10) | −0.00089 (8) | −0.00025 (7) | −0.00423 (7) |
Fe1 | 0.0194 (3) | 0.0265 (3) | 0.0249 (4) | 0.0004 (3) | 0.0013 (3) | −0.0051 (3) |
P1 | 0.0212 (6) | 0.0264 (6) | 0.0210 (6) | 0.0000 (5) | 0.0008 (5) | −0.0009 (5) |
P2 | 0.0200 (6) | 0.0252 (6) | 0.0250 (6) | −0.0006 (5) | 0.0024 (5) | −0.0031 (5) |
S1 | 0.0268 (7) | 0.0415 (7) | 0.0235 (6) | −0.0007 (6) | −0.0051 (5) | −0.0083 (5) |
C1 | 0.019 (2) | 0.027 (2) | 0.023 (2) | 0.002 (2) | 0.0030 (19) | −0.0018 (19) |
C2 | 0.017 (2) | 0.037 (3) | 0.027 (3) | 0.001 (2) | −0.002 (2) | −0.004 (2) |
C3 | 0.025 (3) | 0.044 (3) | 0.021 (3) | 0.007 (2) | −0.002 (2) | −0.005 (2) |
C4 | 0.034 (3) | 0.037 (3) | 0.025 (3) | 0.009 (2) | 0.005 (2) | 0.003 (2) |
C5 | 0.026 (3) | 0.026 (2) | 0.025 (3) | 0.002 (2) | 0.004 (2) | −0.0005 (19) |
C6 | 0.031 (3) | 0.028 (2) | 0.022 (3) | 0.000 (2) | 0.007 (2) | −0.0012 (19) |
C7 | 0.040 (3) | 0.037 (3) | 0.052 (4) | −0.004 (3) | 0.004 (3) | 0.008 (3) |
C8 | 0.062 (5) | 0.033 (3) | 0.085 (5) | −0.002 (3) | 0.006 (4) | 0.015 (3) |
C9 | 0.066 (4) | 0.026 (3) | 0.059 (4) | −0.014 (3) | 0.014 (3) | 0.005 (3) |
C10 | 0.041 (3) | 0.045 (3) | 0.035 (3) | −0.017 (3) | 0.008 (3) | −0.008 (2) |
C11 | 0.027 (3) | 0.039 (3) | 0.030 (3) | −0.003 (2) | 0.005 (2) | −0.001 (2) |
C12 | 0.022 (2) | 0.026 (2) | 0.029 (3) | −0.001 (2) | 0.011 (2) | −0.0021 (19) |
C13 | 0.026 (3) | 0.035 (3) | 0.033 (3) | −0.001 (2) | 0.004 (2) | −0.003 (2) |
C14 | 0.024 (3) | 0.041 (3) | 0.056 (4) | 0.005 (2) | 0.004 (3) | −0.001 (3) |
C15 | 0.034 (3) | 0.039 (3) | 0.053 (4) | 0.008 (3) | 0.019 (3) | −0.004 (3) |
C16 | 0.057 (4) | 0.039 (3) | 0.035 (3) | 0.007 (3) | 0.020 (3) | −0.001 (2) |
C17 | 0.033 (3) | 0.036 (3) | 0.025 (3) | 0.003 (2) | 0.006 (2) | 0.000 (2) |
C18 | 0.019 (2) | 0.029 (2) | 0.028 (3) | 0.004 (2) | 0.002 (2) | −0.011 (2) |
C19 | 0.025 (3) | 0.045 (3) | 0.031 (3) | 0.003 (2) | 0.006 (2) | −0.017 (2) |
C20 | 0.020 (3) | 0.046 (3) | 0.065 (4) | −0.001 (2) | 0.001 (3) | −0.035 (3) |
C21 | 0.024 (3) | 0.023 (2) | 0.078 (5) | −0.001 (2) | 0.006 (3) | −0.005 (3) |
C22 | 0.017 (3) | 0.027 (2) | 0.052 (3) | 0.004 (2) | 0.006 (2) | 0.005 (2) |
C23 | 0.023 (2) | 0.027 (2) | 0.027 (3) | −0.004 (2) | 0.004 (2) | −0.0046 (19) |
C24 | 0.029 (3) | 0.032 (3) | 0.035 (3) | −0.002 (2) | 0.005 (2) | −0.003 (2) |
C25 | 0.043 (3) | 0.026 (3) | 0.052 (4) | 0.002 (2) | 0.000 (3) | 0.001 (2) |
C26 | 0.048 (4) | 0.039 (3) | 0.046 (4) | −0.004 (3) | −0.006 (3) | 0.013 (3) |
C27 | 0.054 (4) | 0.058 (3) | 0.034 (3) | −0.001 (3) | 0.011 (3) | 0.008 (3) |
C28 | 0.039 (3) | 0.038 (3) | 0.033 (3) | 0.007 (2) | 0.011 (2) | −0.002 (2) |
C29 | 0.019 (2) | 0.026 (2) | 0.026 (3) | −0.001 (2) | −0.0004 (19) | 0.0022 (19) |
C30 | 0.025 (3) | 0.034 (3) | 0.037 (3) | −0.001 (2) | 0.003 (2) | −0.006 (2) |
C31 | 0.034 (3) | 0.032 (3) | 0.057 (4) | 0.004 (2) | 0.011 (3) | −0.012 (2) |
C32 | 0.027 (3) | 0.040 (3) | 0.087 (5) | 0.008 (3) | 0.013 (3) | −0.004 (3) |
C33 | 0.023 (3) | 0.047 (3) | 0.117 (6) | 0.002 (3) | −0.012 (3) | −0.024 (4) |
C34 | 0.029 (3) | 0.037 (3) | 0.079 (5) | 0.001 (3) | −0.008 (3) | −0.023 (3) |
O1 | 0.038 (4) | 0.083 (5) | 0.159 (8) | −0.005 (3) | −0.009 (4) | 0.015 (4) |
C35 | 0.090 (10) | 0.089 (9) | 0.155 (16) | −0.001 (7) | 0.001 (9) | 0.010 (8) |
Au1—P1 | 2.2524 (12) | C15—C16 | 1.372 (7) |
Au1—S1 | 2.3036 (12) | C15—H15 | 0.9500 |
Au2—P2 | 2.2452 (12) | C16—C17 | 1.392 (6) |
Au2—S1 | 2.2988 (12) | C16—H16 | 0.9500 |
Au1—Au2 | 2.8857 (3) | C17—H17 | 0.9500 |
Fe1—C1 | 2.029 (4) | C18—C19 | 1.425 (6) |
Fe1—C18 | 2.037 (4) | C18—C22 | 1.426 (6) |
Fe1—C22 | 2.038 (5) | C19—C20 | 1.406 (7) |
Fe1—C2 | 2.041 (4) | C19—H19 | 0.9500 |
Fe1—C4 | 2.042 (5) | C20—C21 | 1.405 (7) |
Fe1—C5 | 2.043 (4) | C20—H20 | 0.9500 |
Fe1—C21 | 2.044 (5) | C21—C22 | 1.416 (7) |
Fe1—C3 | 2.046 (5) | C21—H21 | 0.9500 |
Fe1—C19 | 2.047 (4) | C22—H22 | 0.9500 |
Fe1—C20 | 2.053 (5) | C23—C28 | 1.379 (6) |
P1—C1 | 1.805 (4) | C23—C24 | 1.393 (6) |
P1—C6 | 1.819 (4) | C24—C25 | 1.371 (7) |
P1—C12 | 1.825 (4) | C24—H24 | 0.9500 |
P2—C18 | 1.797 (4) | C25—C26 | 1.374 (7) |
P2—C23 | 1.820 (5) | C25—H25 | 0.9500 |
P2—C29 | 1.822 (4) | C26—C27 | 1.375 (7) |
C1—C2 | 1.423 (6) | C26—H26 | 0.9500 |
C1—C5 | 1.427 (6) | C27—C28 | 1.381 (7) |
C2—C3 | 1.418 (6) | C27—H27 | 0.9500 |
C2—H2 | 0.9500 | C28—H28 | 0.9500 |
C3—C4 | 1.410 (7) | C29—C30 | 1.383 (6) |
C3—H3 | 0.9500 | C29—C34 | 1.388 (7) |
C4—C5 | 1.401 (6) | C30—C31 | 1.381 (6) |
C4—H4 | 0.9500 | C30—H30 | 0.9500 |
C5—H5 | 0.9500 | C31—C32 | 1.356 (7) |
C6—C7 | 1.373 (6) | C31—H31 | 0.9500 |
C6—C11 | 1.389 (6) | C32—C33 | 1.383 (7) |
C7—C8 | 1.392 (7) | C32—H32 | 0.9500 |
C7—H7 | 0.9500 | C33—C34 | 1.378 (7) |
C8—C9 | 1.362 (8) | C33—H33 | 0.9500 |
C8—H8 | 0.9500 | C34—H34 | 0.9500 |
C9—C10 | 1.364 (7) | O1—C35 | 1.378 (18) |
C9—H9 | 0.9500 | O1—H1A | 0.8400 |
C10—C11 | 1.389 (6) | C35—H35A | 0.9800 |
C10—H10 | 0.9500 | C35—H35B | 0.9800 |
C11—H11 | 0.9500 | C35—H35C | 0.9800 |
C12—C17 | 1.383 (6) | O2—C36 | 1.26 (6) |
C12—C13 | 1.393 (6) | O2—H2B | 0.8400 |
C13—C14 | 1.386 (6) | C36—H36A | 0.9800 |
C13—H13 | 0.9500 | C36—H36B | 0.9800 |
C14—C15 | 1.375 (7) | C36—H36C | 0.9800 |
C14—H14 | 0.9500 | ||
S1—Au1—Au2 | 51.10 (3) | C10—C9—H9 | 120.2 |
S1—Au2—Au1 | 51.24 (3) | C9—C10—C11 | 120.5 (5) |
P1—Au1—S1 | 171.06 (4) | C9—C10—H10 | 119.8 |
P2—Au2—S1 | 172.59 (4) | C11—C10—H10 | 119.8 |
P1—Au1—Au2 | 122.96 (3) | C10—C11—C6 | 120.0 (5) |
P2—Au2—Au1 | 122.54 (3) | C10—C11—H11 | 120.0 |
C1—Fe1—C18 | 130.97 (18) | C6—C11—H11 | 120.0 |
C1—Fe1—C22 | 109.71 (19) | C17—C12—C13 | 119.1 (4) |
C18—Fe1—C22 | 40.97 (17) | C17—C12—P1 | 119.2 (4) |
C1—Fe1—C2 | 40.94 (17) | C13—C12—P1 | 121.6 (3) |
C18—Fe1—C2 | 168.62 (18) | C14—C13—C12 | 120.5 (5) |
C22—Fe1—C2 | 128.96 (18) | C14—C13—H13 | 119.8 |
C1—Fe1—C4 | 68.34 (17) | C12—C13—H13 | 119.8 |
C18—Fe1—C4 | 119.05 (18) | C15—C14—C13 | 119.7 (5) |
C22—Fe1—C4 | 153.41 (19) | C15—C14—H14 | 120.2 |
C2—Fe1—C4 | 68.08 (18) | C13—C14—H14 | 120.2 |
C1—Fe1—C5 | 41.03 (16) | C16—C15—C14 | 120.6 (5) |
C18—Fe1—C5 | 110.54 (18) | C16—C15—H15 | 119.7 |
C22—Fe1—C5 | 120.68 (19) | C14—C15—H15 | 119.7 |
C2—Fe1—C5 | 68.50 (18) | C15—C16—C17 | 120.1 (5) |
C4—Fe1—C5 | 40.12 (18) | C15—C16—H16 | 119.9 |
C1—Fe1—C21 | 118.8 (2) | C17—C16—H16 | 119.9 |
C18—Fe1—C21 | 68.06 (18) | C12—C17—C16 | 120.0 (5) |
C22—Fe1—C21 | 40.60 (19) | C12—C17—H17 | 120.0 |
C2—Fe1—C21 | 107.47 (19) | C16—C17—H17 | 120.0 |
C4—Fe1—C21 | 164.5 (2) | C19—C18—C22 | 107.8 (4) |
C5—Fe1—C21 | 153.8 (2) | C19—C18—P2 | 127.6 (4) |
C1—Fe1—C3 | 68.64 (18) | C22—C18—P2 | 124.5 (4) |
C18—Fe1—C3 | 150.45 (19) | C19—C18—Fe1 | 69.9 (2) |
C22—Fe1—C3 | 165.73 (18) | C22—C18—Fe1 | 69.5 (2) |
C2—Fe1—C3 | 40.62 (18) | P2—C18—Fe1 | 128.5 (2) |
C4—Fe1—C3 | 40.36 (19) | C20—C19—C18 | 108.1 (5) |
C5—Fe1—C3 | 68.06 (19) | C20—C19—Fe1 | 70.2 (3) |
C21—Fe1—C3 | 126.7 (2) | C18—C19—Fe1 | 69.2 (2) |
C1—Fe1—C19 | 169.06 (18) | C20—C19—H19 | 125.9 |
C18—Fe1—C19 | 40.85 (18) | C18—C19—H19 | 125.9 |
C22—Fe1—C19 | 68.7 (2) | Fe1—C19—H19 | 126.3 |
C2—Fe1—C19 | 148.51 (19) | C21—C20—C19 | 108.0 (5) |
C4—Fe1—C19 | 108.0 (2) | C21—C20—Fe1 | 69.6 (3) |
C5—Fe1—C19 | 129.69 (19) | C19—C20—Fe1 | 69.7 (3) |
C21—Fe1—C19 | 67.6 (2) | C21—C20—H20 | 126.0 |
C3—Fe1—C19 | 115.7 (2) | C19—C20—H20 | 126.0 |
C1—Fe1—C20 | 150.34 (19) | Fe1—C20—H20 | 126.3 |
C18—Fe1—C20 | 68.17 (18) | C20—C21—C22 | 109.1 (4) |
C22—Fe1—C20 | 68.4 (2) | C20—C21—Fe1 | 70.3 (3) |
C2—Fe1—C20 | 115.72 (19) | C22—C21—Fe1 | 69.5 (2) |
C4—Fe1—C20 | 127.0 (2) | C20—C21—H21 | 125.4 |
C5—Fe1—C20 | 165.7 (2) | C22—C21—H21 | 125.4 |
C21—Fe1—C20 | 40.1 (2) | Fe1—C21—H21 | 126.4 |
C3—Fe1—C20 | 105.7 (2) | C21—C22—C18 | 106.9 (5) |
C19—Fe1—C20 | 40.10 (18) | C21—C22—Fe1 | 69.9 (3) |
C1—P1—C6 | 105.8 (2) | C18—C22—Fe1 | 69.5 (3) |
C1—P1—C12 | 103.0 (2) | C21—C22—H22 | 126.5 |
C6—P1—C12 | 105.18 (19) | C18—C22—H22 | 126.5 |
C1—P1—Au1 | 111.46 (15) | Fe1—C22—H22 | 125.6 |
C6—P1—Au1 | 118.15 (16) | C28—C23—C24 | 118.4 (4) |
C12—P1—Au1 | 112.01 (16) | C28—C23—P2 | 122.8 (3) |
C18—P2—C23 | 104.6 (2) | C24—C23—P2 | 118.8 (3) |
C18—P2—C29 | 104.90 (19) | C25—C24—C23 | 120.7 (4) |
C23—P2—C29 | 104.3 (2) | C25—C24—H24 | 119.7 |
C18—P2—Au2 | 111.26 (15) | C23—C24—H24 | 119.7 |
C23—P2—Au2 | 116.60 (14) | C24—C25—C26 | 120.0 (5) |
C29—P2—Au2 | 114.08 (15) | C24—C25—H25 | 120.0 |
Au2—S1—Au1 | 77.66 (4) | C26—C25—H25 | 120.0 |
C2—C1—C5 | 107.5 (4) | C25—C26—C27 | 120.4 (5) |
C2—C1—P1 | 129.4 (3) | C25—C26—H26 | 119.8 |
C5—C1—P1 | 122.9 (3) | C27—C26—H26 | 119.8 |
C2—C1—Fe1 | 70.0 (2) | C26—C27—C28 | 119.3 (5) |
C5—C1—Fe1 | 70.0 (2) | C26—C27—H27 | 120.3 |
P1—C1—Fe1 | 129.7 (2) | C28—C27—H27 | 120.3 |
C3—C2—C1 | 107.9 (4) | C23—C28—C27 | 121.2 (5) |
C3—C2—Fe1 | 69.9 (3) | C23—C28—H28 | 119.4 |
C1—C2—Fe1 | 69.1 (2) | C27—C28—H28 | 119.4 |
C3—C2—H2 | 126.0 | C30—C29—C34 | 118.7 (4) |
C1—C2—H2 | 126.0 | C30—C29—P2 | 123.2 (4) |
Fe1—C2—H2 | 126.5 | C34—C29—P2 | 118.0 (4) |
C4—C3—C2 | 107.8 (4) | C31—C30—C29 | 120.5 (5) |
C4—C3—Fe1 | 69.7 (3) | C31—C30—H30 | 119.8 |
C2—C3—Fe1 | 69.5 (3) | C29—C30—H30 | 119.8 |
C4—C3—H3 | 126.1 | C32—C31—C30 | 120.5 (5) |
C2—C3—H3 | 126.1 | C32—C31—H31 | 119.7 |
Fe1—C3—H3 | 126.3 | C30—C31—H31 | 119.7 |
C5—C4—C3 | 108.9 (4) | C31—C32—C33 | 119.9 (5) |
C5—C4—Fe1 | 69.9 (3) | C31—C32—H32 | 120.1 |
C3—C4—Fe1 | 69.9 (3) | C33—C32—H32 | 120.1 |
C5—C4—H4 | 125.5 | C34—C33—C32 | 120.1 (5) |
C3—C4—H4 | 125.5 | C34—C33—H33 | 119.9 |
Fe1—C4—H4 | 126.2 | C32—C33—H33 | 119.9 |
C4—C5—C1 | 107.9 (4) | C33—C34—C29 | 120.3 (5) |
C4—C5—Fe1 | 69.9 (3) | C33—C34—H34 | 119.9 |
C1—C5—Fe1 | 69.0 (2) | C29—C34—H34 | 119.9 |
C4—C5—H5 | 126.0 | C35—O1—H1A | 109.5 |
C1—C5—H5 | 126.0 | O1—C35—H35A | 109.5 |
Fe1—C5—H5 | 126.6 | O1—C35—H35B | 109.5 |
C7—C6—C11 | 119.1 (4) | H35A—C35—H35B | 109.5 |
C7—C6—P1 | 119.0 (4) | O1—C35—H35C | 109.5 |
C11—C6—P1 | 121.8 (4) | H35A—C35—H35C | 109.5 |
C6—C7—C8 | 119.9 (5) | H35B—C35—H35C | 109.5 |
C6—C7—H7 | 120.1 | C36—O2—H2B | 109.5 |
C8—C7—H7 | 120.1 | O2—C36—H36A | 109.5 |
C9—C8—C7 | 120.9 (6) | O2—C36—H36B | 109.5 |
C9—C8—H8 | 119.5 | H36A—C36—H36B | 109.5 |
C7—C8—H8 | 119.5 | O2—C36—H36C | 109.5 |
C8—C9—C10 | 119.6 (5) | H36A—C36—H36C | 109.5 |
C8—C9—H9 | 120.2 | H36B—C36—H36C | 109.5 |
C6—P1—C1—C2 | −24.5 (5) | C23—P2—C18—C19 | −28.2 (4) |
C12—P1—C1—C2 | 85.6 (4) | C29—P2—C18—C19 | 81.2 (4) |
Au1—P1—C1—C2 | −154.1 (4) | Au2—P2—C18—C19 | −154.9 (3) |
C6—P1—C1—C5 | 162.0 (4) | C23—P2—C18—C22 | 155.5 (3) |
C12—P1—C1—C5 | −87.9 (4) | C29—P2—C18—C22 | −95.0 (4) |
Au1—P1—C1—C5 | 32.4 (4) | Au2—P2—C18—C22 | 28.8 (4) |
C6—P1—C1—Fe1 | 71.6 (3) | C23—P2—C18—Fe1 | 65.2 (3) |
C12—P1—C1—Fe1 | −178.3 (3) | C29—P2—C18—Fe1 | 174.7 (3) |
Au1—P1—C1—Fe1 | −58.1 (3) | Au2—P2—C18—Fe1 | −61.5 (3) |
C5—C1—C2—C3 | −0.9 (5) | C22—C18—C19—C20 | 0.1 (5) |
P1—C1—C2—C3 | −175.2 (3) | P2—C18—C19—C20 | −176.6 (3) |
Fe1—C1—C2—C3 | 59.3 (3) | Fe1—C18—C19—C20 | 59.6 (3) |
C5—C1—C2—Fe1 | −60.2 (3) | C22—C18—C19—Fe1 | −59.5 (3) |
P1—C1—C2—Fe1 | 125.5 (4) | P2—C18—C19—Fe1 | 123.8 (3) |
C1—C2—C3—C4 | 0.6 (5) | C18—C19—C20—C21 | 0.3 (5) |
Fe1—C2—C3—C4 | 59.4 (3) | Fe1—C19—C20—C21 | 59.3 (3) |
C1—C2—C3—Fe1 | −58.8 (3) | C18—C19—C20—Fe1 | −59.0 (3) |
C2—C3—C4—C5 | 0.0 (5) | C19—C20—C21—C22 | −0.6 (5) |
Fe1—C3—C4—C5 | 59.3 (3) | Fe1—C20—C21—C22 | 58.8 (3) |
C2—C3—C4—Fe1 | −59.3 (3) | C19—C20—C21—Fe1 | −59.4 (3) |
C3—C4—C5—C1 | −0.5 (5) | C20—C21—C22—C18 | 0.6 (5) |
Fe1—C4—C5—C1 | 58.7 (3) | Fe1—C21—C22—C18 | 59.9 (3) |
C3—C4—C5—Fe1 | −59.3 (3) | C20—C21—C22—Fe1 | −59.3 (3) |
C2—C1—C5—C4 | 0.9 (5) | C19—C18—C22—C21 | −0.5 (5) |
P1—C1—C5—C4 | 175.6 (3) | P2—C18—C22—C21 | 176.4 (3) |
Fe1—C1—C5—C4 | −59.3 (3) | Fe1—C18—C22—C21 | −60.2 (3) |
C2—C1—C5—Fe1 | 60.2 (3) | C19—C18—C22—Fe1 | 59.7 (3) |
P1—C1—C5—Fe1 | −125.1 (3) | P2—C18—C22—Fe1 | −123.4 (3) |
C1—P1—C6—C7 | −113.1 (4) | C18—P2—C23—C28 | 82.6 (4) |
C12—P1—C6—C7 | 138.3 (4) | C29—P2—C23—C28 | −27.3 (5) |
Au1—P1—C6—C7 | 12.5 (4) | Au2—P2—C23—C28 | −154.0 (4) |
C1—P1—C6—C11 | 69.6 (4) | C18—P2—C23—C24 | −95.9 (4) |
C12—P1—C6—C11 | −38.9 (4) | C29—P2—C23—C24 | 154.2 (4) |
Au1—P1—C6—C11 | −164.8 (3) | Au2—P2—C23—C24 | 27.4 (4) |
C11—C6—C7—C8 | 0.2 (8) | C28—C23—C24—C25 | 0.0 (7) |
P1—C6—C7—C8 | −177.2 (4) | P2—C23—C24—C25 | 178.7 (4) |
C6—C7—C8—C9 | −1.2 (9) | C23—C24—C25—C26 | −0.1 (8) |
C7—C8—C9—C10 | 0.8 (10) | C24—C25—C26—C27 | 0.3 (9) |
C8—C9—C10—C11 | 0.5 (9) | C25—C26—C27—C28 | −0.4 (9) |
C9—C10—C11—C6 | −1.5 (7) | C24—C23—C28—C27 | −0.1 (8) |
C7—C6—C11—C10 | 1.2 (7) | P2—C23—C28—C27 | −178.7 (4) |
P1—C6—C11—C10 | 178.4 (3) | C26—C27—C28—C23 | 0.3 (9) |
C1—P1—C12—C17 | 152.1 (3) | C18—P2—C29—C30 | −16.6 (4) |
C6—P1—C12—C17 | −97.4 (4) | C23—P2—C29—C30 | 93.1 (4) |
Au1—P1—C12—C17 | 32.2 (4) | Au2—P2—C29—C30 | −138.6 (4) |
C1—P1—C12—C13 | −25.2 (4) | C18—P2—C29—C34 | 165.1 (4) |
C6—P1—C12—C13 | 85.4 (4) | C23—P2—C29—C34 | −85.2 (4) |
Au1—P1—C12—C13 | −145.1 (3) | Au2—P2—C29—C34 | 43.1 (4) |
C17—C12—C13—C14 | 1.6 (7) | C34—C29—C30—C31 | 2.3 (7) |
P1—C12—C13—C14 | 178.9 (4) | P2—C29—C30—C31 | −176.0 (4) |
C12—C13—C14—C15 | −1.3 (7) | C29—C30—C31—C32 | −1.3 (8) |
C13—C14—C15—C16 | 0.1 (8) | C30—C31—C32—C33 | 0.3 (9) |
C14—C15—C16—C17 | 0.7 (8) | C31—C32—C33—C34 | −0.4 (10) |
C13—C12—C17—C16 | −0.8 (7) | C32—C33—C34—C29 | 1.5 (10) |
P1—C12—C17—C16 | −178.1 (3) | C30—C29—C34—C33 | −2.4 (8) |
C15—C16—C17—C12 | −0.4 (7) | P2—C29—C34—C33 | 175.9 (5) |
Cg1 and Cg2 are the centroids of the C7–C11 and C12–C16 phenyl rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···S1 | 0.84 | 2.63 | 3.465 (6) | 170 |
C3—H3···S1i | 0.95 | 2.79 | 3.734 (5) | 175 |
C27—H27···Cg(1)ii | 0.95 | 2.83 | 3.659 (6) | 146 |
C32—H32···Cg(2)iii | 0.95 | 2.88 | 3.717 (6) | 147 |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z+1/2; (iii) −x+1/2, y+1/2, −z+1/2. |
Au1—P1 | 2.2524 (12) | Au2—S1 | 2.2988 (12) |
Au1—S1 | 2.3036 (12) | Au1—Au2 | 2.8857 (3) |
Au2—P2 | 2.2452 (12) | ||
S1—Au1—Au2 | 51.10 (3) | P2—Au2—S1 | 172.59 (4) |
S1—Au2—Au1 | 51.24 (3) | P1—Au1—Au2 | 122.96 (3) |
P1—Au1—S1 | 171.06 (4) | P2—Au2—Au1 | 122.54 (3) |
Cg1 and Cg2 are the centroids of the C7–C11 and C12–C16 phenyl rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···S1 | 0.84 | 2.63 | 3.465 (6) | 170 |
C3—H3···S1i | 0.95 | 2.79 | 3.734 (5) | 175 |
C27—H27···Cg(1)ii | 0.95 | 2.83 | 3.659 (6) | 146 |
C32—H32···Cg(2)iii | 0.95 | 2.88 | 3.717 (6) | 147 |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z+1/2; (iii) −x+1/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Au2Fe(C17H14P)2S]·CH4O |
Mr | 1012.39 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 200 |
a, b, c (Å) | 13.7434 (13), 12.6277 (13), 18.7630 (18) |
β (°) | 98.352 (7) |
V (Å3) | 3221.7 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 9.72 |
Crystal size (mm) | 0.30 × 0.10 × 0.01 |
Data collection | |
Diffractometer | Rigaku VariMax RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.572, 0.995 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26469, 6105, 5445 |
Rint | 0.045 |
(sin θ/λ)max (Å−1) | 0.610 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.052, 1.13 |
No. of reflections | 6105 |
No. of parameters | 392 |
No. of restraints | 8 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.03, −0.55 |
Computer programs: PROCESS-AUTO (Rigaku, 2000), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), DIAMOND (Putz & Brandenburg, 2011), WinGX (Farrugia, 2012).
Acknowledgements
This work was supported by CREST, JST, and a Grant-in-Aid for Science Research No. 25600005 from the Ministry of Education, Culture, Sports, Science and Technology of Japan.
References
Canales, F., Gimeno, M. C., Laguna, A. & Jones, P. G. (1996). J. Am. Chem. Soc. 118, 4839–4845. CSD CrossRef CAS Web of Science Google Scholar
Chen, B.-L., Mok, K.-F. & Ng, S.-C. (1998). J. Chem. Soc. Dalton Trans. pp. 4035–4042. Web of Science CSD CrossRef Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed. 53, 662–671. Web of Science CSD CrossRef CAS Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Hofreiter, S., Paul, M. & Schmidbaur, H. (1995). Chem. Ber. 128, 901–905. CrossRef CAS Web of Science Google Scholar
Putz & Brandenburg (2011). DIAMOND. Crystal Impact, Bonn, Germany. Google Scholar
Rigaku (2000). PROCESS-AUTO. Rigaku Corporation, Tolyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
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