# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof. Simon Lotz' _publ_contact_author_email simon.lotz@up.ac.za _publ_section_title ; Rhenium ethoxy- and hydroxycarbene complexes with thiophene substituents ; loop_ _publ_author_name S.Lotz M.Landman A.Olivier D.Bezuidenhout D.Liles E.Palmer #END data_ao10an_complex_4a _database_code_depnum_ccdc_archive 'CCDC 790280' #TrackingRef '- Lotz_Landman_Olivier_Bezuidenhout_Liles_Palmer.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Octacarbonyl-(\m-hydrido)-(\m-(hydrogen-bis- (oxo-thien-2-yl-methylidene)))-di-rhenium ; _chemical_name_common ; Octacarbonyl-(mu-hydrido)-(mu-(hydrogen-bis-(oxo-thien-2-yl- methylidene)))-di-rhenium ; _chemical_melting_point ? _chemical_formula_moiety 'C18 H8 O10 Re2 S2' _chemical_formula_sum 'C18 H8 O10 Re2 S2' _chemical_formula_weight 820.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.2721(8) _cell_length_b 12.2456(7) _cell_length_c 13.1170(7) _cell_angle_alpha 90.00 _cell_angle_beta 97.280(1) _cell_angle_gamma 90.00 _cell_volume 2274.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8987 _cell_measurement_theta_min 2.591 _cell_measurement_theta_max 26.415 _exptl_crystal_description irregular_fragment _exptl_crystal_colour orange _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas . _exptl_crystal_density_diffrn 2.397 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1512 _exptl_absorpt_coefficient_mu 10.871 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.047 _exptl_absorpt_correction_T_max 0.066 _exptl_absorpt_process_details 'SADABS (Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker (Seimens) P4' _diffrn_measurement_method '\f and \w scans' _diffrn_detector 'SMART 1000 CCD' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 11867 _diffrn_reflns_av_R_equivalents 0.0197 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 26.53 _diffrn_measured_fraction_theta_max 0.890 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _reflns_number_total 4209 _reflns_number_gt 3809 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Bruker, 2001)' _computing_structure_refinement ;SHELXTL and SHELXL-97 (Sheldrick, 1997) ; _computing_molecular_graphics ; ORTEP-3 for Windows (Farrugia, 1997), POV-Ray (Cason, 2004) ; _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Both thiophene rings exhibited some disorder with, in each case, a minor component rotated appoximately 180\% about the C(ring)---C(carbene) bond with respect to the major component. The atoms of the major components were refined freely. The minor components were refined as rigid bodies with the ring geometry derived from a molecular mechanics calculation and an overall isotropic displacement paramenter for each ring. Site occupation factors were refined for both the major and minor components, but with the sofs for each pair constrained to sum to 1.0. The sofs of the major components refined to 0.938(5) and 0.878(6). All hydrogen atom positions, except for those for the minor orientations of the thiophene rings, were observed on difference maps. However, except for the bridging hydrogens - H1 and H10, all were included in the refinement in calculated positions with their adps set to 1.2 x equivalent isotropic adp (or isotropic adp) of the atom to which they are bonded. The coordinates and isotropic adps of H1 and H10 were freely refined. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0194P)^2^+2.1559P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00095(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4209 _refine_ls_number_parameters 314 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0209 _refine_ls_R_factor_gt 0.0179 _refine_ls_wR_factor_ref 0.0466 _refine_ls_wR_factor_gt 0.0451 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.687 _refine_diff_density_min -0.569 _refine_diff_density_rms 0.079 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Re1 Re 0.362171(10) 0.951220(12) 0.168441(11) 0.04136(6) Uani 1 1 d . . . Re2 Re 0.272875(10) 1.053595(11) 0.373569(10) 0.03827(6) Uani 1 1 d . . . H1 H 0.288(3) 0.969(3) 0.265(3) 0.068(13) Uiso 1 1 d . . . C1 C 0.4178(3) 0.9046(4) 0.0494(3) 0.0553(10) Uani 1 1 d . . . O1 O 0.4487(3) 0.8746(3) -0.0208(3) 0.0820(10) Uani 1 1 d . . . C2 C 0.3420(3) 0.7954(4) 0.2035(3) 0.0597(10) Uani 1 1 d . . . O2 O 0.3322(3) 0.7079(3) 0.2267(3) 0.0991(12) Uani 1 1 d . . . C3 C 0.4866(3) 0.9486(3) 0.2541(4) 0.0576(10) Uani 1 1 d . . . O3 O 0.5590(2) 0.9479(3) 0.3013(3) 0.0907(12) Uani 1 1 d . . . C4 C 0.3779(3) 1.1087(4) 0.1387(3) 0.0532(9) Uani 1 1 d . . . O4 O 0.3883(2) 1.1987(3) 0.1214(3) 0.0751(9) Uani 1 1 d . . . C5 C 0.2318(3) 1.1296(3) 0.4897(3) 0.0534(9) Uani 1 1 d . . . O5 O 0.2081(2) 1.1760(3) 0.5571(3) 0.0797(10) Uani 1 1 d . . . C6 C 0.3621(3) 0.9567(3) 0.4612(3) 0.0556(10) Uani 1 1 d . . . O6 O 0.4112(3) 0.8992(3) 0.5077(3) 0.0945(12) Uani 1 1 d . . . C7 C 0.3707(3) 1.1659(3) 0.3656(3) 0.0489(9) Uani 1 1 d . . . O7 O 0.4263(2) 1.2322(3) 0.3617(2) 0.0764(9) Uani 1 1 d . . . C8 C 0.1784(3) 1.1334(3) 0.2766(3) 0.0507(9) Uani 1 1 d . . . O8 O 0.1226(2) 1.1752(3) 0.2220(3) 0.0823(10) Uani 1 1 d . . . C9 C 0.2244(3) 0.9626(3) 0.0800(3) 0.0428(8) Uani 1 1 d . . . O9 O 0.1480(2) 0.9386(2) 0.1155(2) 0.0548(7) Uani 1 1 d . . . C10 C 0.1650(3) 0.9283(3) 0.3727(3) 0.0452(8) Uani 1 1 d . . . O10 O 0.1258(2) 0.8846(2) 0.28910(19) 0.0589(7) Uani 1 1 d . . . H10 H 0.149(5) 0.912(6) 0.201(6) 0.15(3) Uiso 1 1 d . . . C11 C 0.2068(3) 1.0021(4) -0.0251(3) 0.0443(10) Uani 0.938(5) 1 d P A 1 S1 S 0.09130(9) 1.00616(13) -0.08606(9) 0.0630(5) Uani 0.938(5) 1 d P A 1 C12 C 0.2671(6) 1.0426(7) -0.0924(6) 0.057(2) Uani 0.938(5) 1 d P A 1 H12 H 0.3325 1.0448 -0.0773 0.068 Uiso 0.938(5) 1 calc PR A 1 C13 C 0.2178(4) 1.0791(6) -0.1849(4) 0.0654(14) Uani 0.938(5) 1 d P A 1 H13 H 0.2468 1.1113 -0.2370 0.078 Uiso 0.938(5) 1 calc PR A 1 C14 C 0.1252(4) 1.0632(6) -0.1906(4) 0.0665(17) Uani 0.938(5) 1 d P A 1 H14 H 0.0831 1.0822 -0.2479 0.080 Uiso 0.938(5) 1 calc PR A 1 C11A C 0.182(3) 1.016(6) -0.036(4) 0.042(6) Uiso 0.062(5) 1 d PG A 2 S1A S 0.284(2) 1.059(3) -0.081(3) 0.042(6) Uiso 0.062(5) 1 d PG A 2 C12A C 0.109(2) 1.023(5) -0.119(5) 0.042(6) Uiso 0.062(5) 1 d PG A 2 H12A H 0.0468 1.0035 -0.1137 0.050(7) Uiso 0.062(5) 1 calc PR A 2 C13A C 0.138(4) 1.061(7) -0.212(4) 0.042(6) Uiso 0.062(5) 1 d PG A 2 H13A H 0.0967 1.0688 -0.2723 0.050(7) Uiso 0.062(5) 1 calc PR A 2 C14A C 0.235(4) 1.085(7) -0.205(3) 0.042(6) Uiso 0.062(5) 1 d PG A 2 H14A H 0.2662 1.1113 -0.2581 0.050(7) Uiso 0.062(5) 1 calc PR A 2 C15 C 0.1278(4) 0.8881(4) 0.4632(4) 0.0411(11) Uani 0.878(6) 1 d P B 1 S2 S 0.03210(18) 0.8012(2) 0.44634(16) 0.0704(6) Uani 0.878(6) 1 d P B 1 C16 C 0.1588(11) 0.9099(12) 0.5675(9) 0.082(6) Uani 0.878(6) 1 d P B 1 H16 H 0.2077 0.9567 0.5925 0.098 Uiso 0.878(6) 1 calc PR B 1 C17 C 0.1014(5) 0.8467(6) 0.6284(4) 0.0647(16) Uani 0.878(6) 1 d P B 1 H17 H 0.1117 0.8454 0.6999 0.078 Uiso 0.878(6) 1 calc PR B 1 C18 C 0.0332(5) 0.7907(7) 0.5750(5) 0.0690(19) Uani 0.878(6) 1 d P B 1 H18 H -0.0104 0.7493 0.6053 0.083 Uiso 0.878(6) 1 calc PR B 1 C15A C 0.115(4) 0.866(4) 0.4512(19) 0.058(5) Uiso 0.122(6) 1 d PG B 2 S2A S 0.1584(15) 0.903(2) 0.575(2) 0.058(5) Uiso 0.122(6) 1 d PG B 2 C16A C 0.032(4) 0.804(5) 0.457(4) 0.058(5) Uiso 0.122(6) 1 d PG B 2 H16A H -0.0037 0.7748 0.3997 0.070(7) Uiso 0.122(6) 1 calc PR B 2 C17A C 0.009(3) 0.789(4) 0.558(4) 0.058(5) Uiso 0.122(6) 1 d PG B 2 H17A H -0.0431 0.7497 0.5721 0.070(7) Uiso 0.122(6) 1 calc PR B 2 C18A C 0.072(2) 0.839(4) 0.635(3) 0.058(5) Uiso 0.122(6) 1 d PG B 2 H18A H 0.0685 0.8384 0.7048 0.070(7) Uiso 0.122(6) 1 calc PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Re1 0.03858(10) 0.04447(10) 0.04135(9) 0.00021(6) 0.00629(6) 0.00367(6) Re2 0.03675(9) 0.04090(10) 0.03649(9) 0.00001(5) 0.00213(6) -0.00406(5) C1 0.052(2) 0.057(2) 0.059(2) 0.001(2) 0.0137(19) 0.0093(19) O1 0.094(2) 0.092(3) 0.067(2) -0.0016(18) 0.0378(18) 0.026(2) C2 0.065(3) 0.052(2) 0.059(2) 0.001(2) -0.0027(19) 0.003(2) O2 0.127(3) 0.055(2) 0.112(3) 0.017(2) 0.002(2) -0.010(2) C3 0.049(2) 0.059(3) 0.064(2) -0.0062(19) 0.003(2) 0.0054(18) O3 0.056(2) 0.102(3) 0.106(3) -0.015(2) -0.022(2) 0.0108(18) C4 0.042(2) 0.058(3) 0.060(2) 0.001(2) 0.0085(17) 0.0099(19) O4 0.088(2) 0.0533(19) 0.089(2) 0.0090(17) 0.0285(18) 0.0052(17) C5 0.050(2) 0.055(2) 0.056(2) -0.0033(19) 0.0084(18) -0.0096(18) O5 0.084(2) 0.088(2) 0.072(2) -0.0339(18) 0.0286(17) -0.0089(19) C6 0.055(2) 0.059(3) 0.051(2) 0.0037(18) -0.0035(18) 0.0000(19) O6 0.095(3) 0.091(3) 0.088(2) 0.020(2) -0.024(2) 0.025(2) C7 0.044(2) 0.053(2) 0.049(2) -0.0005(17) 0.0011(16) -0.0028(18) O7 0.070(2) 0.073(2) 0.084(2) 0.0005(17) 0.0027(16) -0.0341(18) C8 0.048(2) 0.048(2) 0.054(2) 0.0071(18) 0.0008(17) -0.0027(18) O8 0.079(2) 0.074(2) 0.086(2) 0.0190(18) -0.0205(18) 0.0076(18) C9 0.0395(19) 0.049(2) 0.0412(18) -0.0034(15) 0.0089(15) -0.0025(15) O9 0.0474(16) 0.076(2) 0.0406(14) 0.0032(13) 0.0043(12) -0.0087(13) C10 0.045(2) 0.046(2) 0.0446(19) 0.0003(16) 0.0051(15) -0.0015(16) O10 0.0667(18) 0.0721(19) 0.0378(13) -0.0059(13) 0.0058(12) -0.0278(15) C11 0.044(2) 0.047(2) 0.040(2) 0.0020(17) 0.0019(17) 0.006(2) S1 0.0553(8) 0.0808(9) 0.0504(7) 0.0054(6) -0.0029(5) 0.0007(6) C12 0.064(4) 0.063(5) 0.042(3) 0.006(3) -0.001(3) -0.006(3) C13 0.086(4) 0.072(3) 0.040(2) 0.014(2) 0.016(2) 0.007(3) C14 0.081(4) 0.074(3) 0.040(3) 0.001(3) -0.011(3) 0.007(3) C15 0.050(3) 0.033(3) 0.041(2) -0.0017(17) 0.0072(18) -0.0083(19) S2 0.0673(9) 0.0800(10) 0.0637(9) 0.0069(7) 0.0082(7) -0.0327(7) C16 0.113(9) 0.091(8) 0.042(4) 0.023(3) 0.015(3) -0.027(4) C17 0.088(5) 0.063(3) 0.047(2) 0.011(2) 0.021(3) -0.010(3) C18 0.073(4) 0.070(3) 0.069(5) 0.021(3) 0.027(4) -0.013(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 C1 1.926(4) . ? Re1 C3 1.978(4) . ? Re1 C4 1.985(5) . ? Re1 C2 1.992(4) . ? Re1 C9 2.158(4) . ? Re1 H1 1.76(4) . ? Re1 Re2 3.3622(2) . ? Re2 C5 1.938(4) . ? Re2 C7 1.972(4) . ? Re2 C8 1.989(4) . ? Re2 C6 1.995(4) . ? Re2 C10 2.173(4) . ? Re2 H1 1.80(4) . ? C1 O1 1.131(5) . ? C2 O2 1.127(5) . ? C3 O3 1.134(5) . ? C4 O4 1.139(5) . ? C5 O5 1.138(5) . ? C6 O6 1.118(5) . ? C7 O7 1.140(5) . ? C8 O8 1.125(4) . ? C9 O9 1.273(4) . ? C9 C11 1.453(5) . ? C9 C11A 1.70(5) . ? O9 H10 1.16(7) . ? C10 O10 1.283(4) . ? C10 C15 1.446(6) . ? C10 C15A 1.53(4) . ? O10 H10 1.29(7) . ? C11 C12 1.400(9) . ? C11 S1 1.739(4) . ? S1 C14 1.665(6) . ? C12 C13 1.396(9) . ? C12 H12 0.9300 . ? C13 C14 1.329(7) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C11A C12A 1.4079 . ? C11A S1A 1.7279 . ? S1A C14A 1.7237 . ? C12A C13A 1.4106 . ? C12A H12A 0.9300 . ? C13A C14A 1.4045 . ? C13A H13A 0.9300 . ? C14A H14A 0.9300 . ? C15 C16 1.409(13) . ? C15 S2 1.724(5) . ? S2 C18 1.691(6) . ? C16 C17 1.441(14) . ? C16 H16 0.9300 . ? C17 C18 1.318(7) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C15A C16A 1.4080 . ? C15A S2A 1.7280 . ? S2A C18A 1.7237 . ? C16A C17A 1.4105 . ? C16A H16A 0.9300 . ? C17A C18A 1.4045 . ? C17A H17A 0.9300 . ? C18A H18A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Re1 C3 91.32(18) . . ? C1 Re1 C4 93.46(17) . . ? C3 Re1 C4 90.63(16) . . ? C1 Re1 C2 89.38(18) . . ? C3 Re1 C2 89.95(17) . . ? C4 Re1 C2 177.08(17) . . ? C1 Re1 C9 91.43(15) . . ? C3 Re1 C9 176.55(15) . . ? C4 Re1 C9 87.13(15) . . ? C2 Re1 C9 92.15(15) . . ? C1 Re1 H1 164.9(14) . . ? C3 Re1 H1 99.8(14) . . ? C4 Re1 H1 96.6(13) . . ? C2 Re1 H1 80.5(13) . . ? C9 Re1 H1 77.9(14) . . ? C5 Re2 C7 89.63(16) . . ? C5 Re2 C8 91.07(17) . . ? C7 Re2 C8 92.87(15) . . ? C5 Re2 C6 93.88(17) . . ? C7 Re2 C6 92.35(16) . . ? C8 Re2 C6 172.82(16) . . ? C5 Re2 C10 93.36(15) . . ? C7 Re2 C10 176.61(14) . . ? C8 Re2 C10 85.49(15) . . ? C6 Re2 C10 89.03(15) . . ? C5 Re2 H1 168.3(14) . . ? C7 Re2 H1 101.7(14) . . ? C8 Re2 H1 85.2(13) . . ? C6 Re2 H1 88.9(13) . . ? C10 Re2 H1 75.3(14) . . ? O1 C1 Re1 177.9(4) . . ? O2 C2 Re1 177.5(4) . . ? O3 C3 Re1 178.4(4) . . ? O4 C4 Re1 179.0(4) . . ? O5 C5 Re2 178.8(4) . . ? O6 C6 Re2 177.3(4) . . ? O7 C7 Re2 178.8(4) . . ? O8 C8 Re2 177.2(4) . . ? O9 C9 C11 111.7(3) . . ? O9 C9 C11A 101.0(12) . . ? O9 C9 Re1 123.6(3) . . ? C11 C9 Re1 124.6(3) . . ? C11A C9 Re1 134.9(12) . . ? C9 O9 H10 120(3) . . ? O10 C10 C15 113.2(3) . . ? O10 C10 C15A 100.1(11) . . ? O10 C10 Re2 122.0(3) . . ? C15 C10 Re2 124.7(3) . . ? C15A C10 Re2 137.8(11) . . ? C10 O10 H10 122(3) . . ? C12 C11 C9 132.1(5) . . ? C12 C11 S1 108.8(4) . . ? C9 C11 S1 119.1(3) . . ? C14 S1 C11 91.9(3) . . ? C13 C12 C11 112.3(7) . . ? C13 C12 H12 123.9 . . ? C11 C12 H12 123.9 . . ? C14 C13 C12 113.0(5) . . ? C14 C13 H13 123.5 . . ? C12 C13 H13 123.5 . . ? C13 C14 S1 113.9(4) . . ? C13 C14 H14 123.0 . . ? S1 C14 H14 123.0 . . ? C12A C11A C9 149(3) . . ? C12A C11A S1A 107.1 . . ? C9 C11A S1A 101(3) . . ? C14A S1A C11A 96.4 . . ? C11A C12A C13A 114.7 . . ? C11A C12A H12A 122.7 . . ? C13A C12A H12A 122.7 . . ? C14A C13A C12A 114.2 . . ? C14A C13A H13A 122.9 . . ? C12A C13A H13A 122.9 . . ? C13A C14A S1A 107.6 . . ? C13A C14A H14A 126.2 . . ? S1A C14A H14A 126.2 . . ? C16 C15 C10 129.0(6) . . ? C16 C15 S2 112.8(6) . . ? C10 C15 S2 118.2(3) . . ? C18 S2 C15 90.7(3) . . ? C15 C16 C17 107.8(10) . . ? C15 C16 H16 126.1 . . ? C17 C16 H16 126.1 . . ? C18 C17 C16 114.7(6) . . ? C18 C17 H17 122.6 . . ? C16 C17 H17 122.6 . . ? C17 C18 S2 113.9(4) . . ? C17 C18 H18 123.1 . . ? S2 C18 H18 123.1 . . ? C16A C15A C10 141(2) . . ? C16A C15A S2A 107.1 . . ? C10 C15A S2A 111(2) . . ? C18A S2A C15A 96.4 . . ? C15A C16A C17A 114.7 . . ? C15A C16A H16A 122.7 . . ? C17A C16A H16A 122.7 . . ? C18A C17A C16A 114.2 . . ? C18A C17A H17A 122.9 . . ? C16A C17A H17A 122.9 . . ? C17A C18A S2A 107.6 . . ? C17A C18A H18A 126.2 . . ? S2A C18A H18A 126.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Re1 C9 O9 144.1(3) . . . . ? C4 Re1 C9 O9 -122.5(3) . . . . ? C2 Re1 C9 O9 54.6(3) . . . . ? C1 Re1 C9 C11 -38.4(4) . . . . ? C4 Re1 C9 C11 55.0(3) . . . . ? C2 Re1 C9 C11 -127.8(4) . . . . ? C1 Re1 C9 C11A -46(3) . . . . ? C4 Re1 C9 C11A 47(3) . . . . ? C2 Re1 C9 C11A -135(3) . . . . ? C5 Re2 C10 O10 145.6(3) . . . . ? C8 Re2 C10 O10 54.8(3) . . . . ? C6 Re2 C10 O10 -120.6(3) . . . . ? C5 Re2 C10 C15 -32.3(4) . . . . ? C8 Re2 C10 C15 -123.1(4) . . . . ? C6 Re2 C10 C15 61.5(4) . . . . ? C5 Re2 C10 C15A -35(3) . . . . ? C8 Re2 C10 C15A -126(3) . . . . ? C6 Re2 C10 C15A 58(3) . . . . ? O9 C9 C11 C12 176.3(6) . . . . ? C11A C9 C11 C12 151(11) . . . . ? Re1 C9 C11 C12 -1.5(8) . . . . ? O9 C9 C11 S1 -2.3(5) . . . . ? C11A C9 C11 S1 -27(11) . . . . ? Re1 C9 C11 S1 179.9(2) . . . . ? C12 C11 S1 C14 -2.2(5) . . . . ? C9 C11 S1 C14 176.7(4) . . . . ? C9 C11 C12 C13 -175.5(6) . . . . ? S1 C11 C12 C13 3.2(7) . . . . ? C11 C12 C13 C14 -2.8(8) . . . . ? C12 C13 C14 S1 1.1(7) . . . . ? C11 S1 C14 C13 0.7(5) . . . . ? O9 C9 C11A C12A -26(7) . . . . ? Re1 C9 C11A C12A 163(5) . . . . ? O9 C9 C11A S1A 176(2) . . . . ? C11 C9 C11A S1A -28(9) . . . . ? Re1 C9 C11A S1A 4(5) . . . . ? C12A C11A S1A C14A 0.3 . . . . ? C9 C11A S1A C14A 169(5) . . . . ? C9 C11A C12A C13A -158(9) . . . . ? S1A C11A C12A C13A -0.3 . . . . ? C11A C12A C13A C14A 0.1 . . . . ? C12A C13A C14A S1A 0.1 . . . . ? C11A S1A C14A C13A -0.2 . . . . ? O10 C10 C15 C16 173.9(9) . . . . ? Re2 C10 C15 C16 -8.0(11) . . . . ? O10 C10 C15 S2 -6.2(5) . . . . ? C15A C10 C15 S2 -17(10) . . . . ? Re2 C10 C15 S2 171.9(2) . . . . ? C16 C15 S2 C18 -1.0(8) . . . . ? C10 C15 S2 C18 179.1(5) . . . . ? C10 C15 C16 C17 -177.5(7) . . . . ? S2 C15 C16 C17 2.6(11) . . . . ? C15 C16 C17 C18 -3.5(12) . . . . ? C16 C17 C18 S2 2.9(9) . . . . ? C15 S2 C18 C17 -1.1(5) . . . . ? O10 C10 C15A C16A -20(4) . . . . ? Re2 C10 C15A C16A 161(3) . . . . ? O10 C10 C15A S2A 177(2) . . . . ? Re2 C10 C15A S2A -2(5) . . . . ? C16A C15A S2A C18A 0.3 . . . . ? C10 C15A S2A C18A 169(4) . . . . ? C10 C15A C16A C17A -164(6) . . . . ? S2A C15A C16A C17A -0.3 . . . . ? C15A C16A C17A C18A 0.1 . . . . ? C16A C17A C18A S2A 0.1 . . . . ? C15A S2A C18A C17A -0.2 . . . . ? # Attachment '- Lotz_Landman_Olivier_Bezuidenhout_Liles_Palmer.cif' data_dbmc9f2_complex_1a _database_code_depnum_ccdc_archive 'CCDC 824376' #TrackingRef '- Lotz_Landman_Olivier_Bezuidenhout_Liles_Palmer.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; nonacarbonyl-(ethoxy-thien-2-yl-methylidene)-di-rhenium ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H8 O10 Re2 S' _chemical_formula_sum 'C16 H8 O10 Re2 S' _chemical_formula_weight 764.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.5491(6) _cell_length_b 13.0140(8) _cell_length_c 16.4648(10) _cell_angle_alpha 90.00 _cell_angle_beta 101.206(1) _cell_angle_gamma 90.00 _cell_volume 2007.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8379 _cell_measurement_theta_min 2.522 _cell_measurement_theta_max 26.492 _exptl_crystal_description plate _exptl_crystal_colour dark-yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas . _exptl_crystal_density_diffrn 2.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1400 _exptl_absorpt_coefficient_mu 12.206 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.067 _exptl_absorpt_correction_T_max 0.231 _exptl_absorpt_process_details 'SADABS (Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker (Seimens) P4' _diffrn_measurement_method '\f and \w scans' _diffrn_detector 'SMART 1000 CCD' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 10576 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 26.53 _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _reflns_number_total 3829 _reflns_number_gt 3545 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Bruker, 2001)' _computing_structure_refinement ;SHELXTL and SHELXL-97 (Sheldrick, 1997) ; _computing_molecular_graphics ; ORTEP-3 for Windows (Farrugia, 1997), POV-Ray (Cason, 2004) ; _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+1.1668P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00126(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3829 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0297 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0705 _refine_ls_wR_factor_gt 0.0690 _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_restrained_S_all 1.127 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 1.444 _refine_diff_density_min -1.213 _refine_diff_density_rms 0.162 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Re1 Re 0.53349(2) 0.065068(15) 0.193204(11) 0.03538(9) Uani 1 1 d . . . Re2 Re 0.85693(2) 0.019919(14) 0.238859(11) 0.03368(9) Uani 1 1 d . . . C1 C 0.3325(6) 0.0920(4) 0.1569(3) 0.0453(12) Uani 1 1 d . . . O1 O 0.2145(5) 0.1080(4) 0.1333(3) 0.0647(11) Uani 1 1 d . . . C2 C 0.5469(6) 0.1636(4) 0.2864(3) 0.0455(12) Uani 1 1 d . . . O2 O 0.5504(5) 0.2171(4) 0.3407(3) 0.0685(12) Uani 1 1 d . . . C3 C 0.5923(6) 0.1736(4) 0.1205(3) 0.0428(12) Uani 1 1 d . . . O3 O 0.6273(5) 0.2339(3) 0.0798(3) 0.0626(11) Uani 1 1 d . . . C4 C 0.5354(6) -0.0399(4) 0.1066(3) 0.0477(13) Uani 1 1 d . . . O4 O 0.5369(6) -0.1011(3) 0.0575(3) 0.0696(13) Uani 1 1 d . . . C5 C 0.5049(6) -0.0466(4) 0.2707(4) 0.0469(12) Uani 1 1 d . . . O5 O 0.4891(5) -0.1108(4) 0.3143(3) 0.0691(13) Uani 1 1 d . . . C6 C 1.0549(6) -0.0180(4) 0.2687(3) 0.0477(13) Uani 1 1 d . . . O6 O 1.1728(5) -0.0413(4) 0.2855(4) 0.0735(14) Uani 1 1 d . . . C7 C 0.9058(6) 0.1613(4) 0.2083(3) 0.0472(12) Uani 1 1 d . . . O7 O 0.9359(5) 0.2356(3) 0.1815(3) 0.0636(11) Uani 1 1 d . . . C8 C 0.8473(7) -0.0055(4) 0.1192(4) 0.0491(13) Uani 1 1 d . . . O8 O 0.8423(6) -0.0180(4) 0.0509(3) 0.0744(14) Uani 1 1 d . . . C9 C 0.7896(6) -0.1237(4) 0.2400(3) 0.0428(11) Uani 1 1 d . . . O9 O 0.7531(5) -0.2071(3) 0.2304(3) 0.0630(11) Uani 1 1 d . . . C10 C 0.8385(5) 0.0505(4) 0.3631(3) 0.0385(11) Uani 1 1 d . . . O10 O 0.8493(4) 0.1392(3) 0.4045(2) 0.0474(9) Uani 1 1 d . . . S1 S 0.7169(3) 0.01201(16) 0.49851(12) 0.0838(6) Uani 1 1 d . . . C11 C 0.8034(6) -0.0261(4) 0.4209(3) 0.0420(12) Uani 1 1 d . . . C12 C 0.8270(7) -0.1323(4) 0.4250(3) 0.0502(13) Uani 1 1 d . . . H12 H 0.8717 -0.1685 0.3885 0.060 Uiso 1 1 calc R . . C13 C 0.7751(8) -0.1774(5) 0.4907(4) 0.0670(18) Uani 1 1 d . . . H13 H 0.7841 -0.2470 0.5035 0.080 Uiso 1 1 calc R . . C14 C 0.7121(10) -0.1106(7) 0.5326(5) 0.087(2) Uani 1 1 d . . . H14 H 0.6692 -0.1292 0.5766 0.105 Uiso 1 1 calc R . . C15 C 0.8825(7) 0.2359(4) 0.3710(4) 0.0560(15) Uani 1 1 d . . . H15A H 0.8167 0.2500 0.3194 0.067 Uiso 1 1 calc R . . H15B H 0.9789 0.2351 0.3603 0.067 Uiso 1 1 calc R . . C16 C 0.8685(8) 0.3168(5) 0.4350(4) 0.0715(19) Uani 1 1 d . . . H16A H 0.7714 0.3195 0.4425 0.107 Uiso 1 1 calc R . . H16B H 0.8955 0.3826 0.4165 0.107 Uiso 1 1 calc R . . H16C H 0.9299 0.2996 0.4866 0.107 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Re1 0.03407(14) 0.03628(14) 0.03609(13) 0.00215(7) 0.00758(9) 0.00061(7) Re2 0.03263(14) 0.03589(14) 0.03446(13) 0.00047(7) 0.01135(9) 0.00023(7) C1 0.043(3) 0.050(3) 0.043(3) 0.002(2) 0.008(2) 0.003(2) O1 0.042(2) 0.074(3) 0.075(3) 0.005(2) 0.003(2) 0.007(2) C2 0.040(3) 0.050(3) 0.048(3) 0.001(2) 0.013(2) 0.007(2) O2 0.070(3) 0.074(3) 0.059(3) -0.022(2) 0.006(2) 0.016(2) C3 0.051(3) 0.039(3) 0.038(2) -0.002(2) 0.009(2) -0.001(2) O3 0.079(3) 0.058(2) 0.054(2) 0.007(2) 0.021(2) -0.011(2) C4 0.052(3) 0.043(3) 0.045(3) 0.008(2) 0.002(2) -0.005(2) O4 0.106(4) 0.054(3) 0.048(2) -0.012(2) 0.011(2) -0.009(3) C5 0.036(3) 0.048(3) 0.058(3) 0.004(3) 0.012(3) -0.003(2) O5 0.061(3) 0.075(3) 0.074(3) 0.032(3) 0.019(2) 0.002(2) C6 0.044(3) 0.056(4) 0.045(3) 0.003(2) 0.014(2) 0.004(3) O6 0.041(3) 0.086(4) 0.093(4) 0.014(3) 0.013(2) 0.014(2) C7 0.047(3) 0.043(3) 0.053(3) -0.005(2) 0.014(2) -0.004(2) O7 0.074(3) 0.049(2) 0.072(3) 0.009(2) 0.024(2) -0.018(2) C8 0.056(4) 0.045(3) 0.050(3) 0.006(2) 0.017(3) 0.005(3) O8 0.103(4) 0.088(4) 0.037(2) -0.004(2) 0.025(2) 0.007(3) C9 0.037(3) 0.042(3) 0.048(3) 0.002(2) 0.006(2) 0.001(2) O9 0.068(3) 0.045(2) 0.071(3) 0.003(2) 0.003(2) -0.005(2) C10 0.035(3) 0.040(3) 0.041(3) 0.000(2) 0.010(2) 0.004(2) O10 0.056(2) 0.042(2) 0.0458(19) -0.0075(16) 0.0156(17) -0.0045(18) S1 0.1241(18) 0.0738(12) 0.0718(11) 0.0050(9) 0.0640(13) 0.0123(11) C11 0.046(3) 0.050(3) 0.032(2) 0.003(2) 0.014(2) 0.006(2) C12 0.063(4) 0.053(3) 0.036(3) 0.010(2) 0.012(2) 0.009(3) C13 0.083(5) 0.065(4) 0.053(3) 0.015(3) 0.013(3) -0.002(4) C14 0.112(7) 0.099(6) 0.064(4) 0.021(4) 0.048(5) -0.004(5) C15 0.062(4) 0.045(3) 0.067(4) -0.012(3) 0.027(3) -0.006(3) C16 0.090(5) 0.051(4) 0.082(4) -0.025(3) 0.037(4) -0.016(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 C1 1.928(6) . ? Re1 C4 1.977(6) . ? Re1 C2 1.984(6) . ? Re1 C5 1.988(6) . ? Re1 C3 2.002(5) . ? Re1 Re2 3.0899(3) . ? Re2 C6 1.923(6) . ? Re2 C9 1.978(5) . ? Re2 C8 1.982(6) . ? Re2 C7 1.987(6) . ? Re2 C10 2.125(5) . ? C1 O1 1.137(6) . ? C2 O2 1.129(7) . ? C3 O3 1.123(6) . ? C4 O4 1.136(7) . ? C5 O5 1.129(7) . ? C6 O6 1.146(7) . ? C7 O7 1.123(6) . ? C8 O8 1.129(7) . ? C9 O9 1.141(6) . ? C10 O10 1.335(6) . ? C10 C11 1.461(7) . ? O10 C15 1.434(7) . ? S1 C14 1.695(8) . ? S1 C11 1.723(5) . ? C11 C12 1.400(8) . ? C12 C13 1.403(8) . ? C12 H12 0.9300 . ? C13 C14 1.326(11) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.514(8) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Re1 C4 92.9(2) . . ? C1 Re1 C2 91.9(2) . . ? C4 Re1 C2 174.7(2) . . ? C1 Re1 C5 94.5(2) . . ? C4 Re1 C5 88.8(2) . . ? C2 Re1 C5 88.4(2) . . ? C1 Re1 C3 93.7(2) . . ? C4 Re1 C3 90.7(2) . . ? C2 Re1 C3 91.3(2) . . ? C5 Re1 C3 171.8(2) . . ? C1 Re1 Re2 176.09(15) . . ? C4 Re1 Re2 83.98(18) . . ? C2 Re1 Re2 91.34(15) . . ? C5 Re1 Re2 87.73(16) . . ? C3 Re1 Re2 84.04(16) . . ? C6 Re2 C9 93.4(2) . . ? C6 Re2 C8 93.7(2) . . ? C9 Re2 C8 84.2(2) . . ? C6 Re2 C7 92.0(2) . . ? C9 Re2 C7 166.0(2) . . ? C8 Re2 C7 82.6(2) . . ? C6 Re2 C10 93.6(2) . . ? C9 Re2 C10 94.6(2) . . ? C8 Re2 C10 172.6(2) . . ? C7 Re2 C10 97.9(2) . . ? C6 Re2 Re1 175.97(17) . . ? C9 Re2 Re1 82.58(15) . . ? C8 Re2 Re1 86.49(18) . . ? C7 Re2 Re1 92.02(17) . . ? C10 Re2 Re1 86.14(14) . . ? O1 C1 Re1 178.1(5) . . ? O2 C2 Re1 177.0(5) . . ? O3 C3 Re1 179.0(5) . . ? O4 C4 Re1 179.2(5) . . ? O5 C5 Re1 179.3(6) . . ? O6 C6 Re2 179.1(6) . . ? O7 C7 Re2 170.8(5) . . ? O8 C8 Re2 178.7(6) . . ? O9 C9 Re2 171.2(5) . . ? O10 C10 C11 105.2(4) . . ? O10 C10 Re2 129.9(4) . . ? C11 C10 Re2 124.9(4) . . ? C10 O10 C15 124.3(4) . . ? C14 S1 C11 91.3(3) . . ? C12 C11 C10 130.4(5) . . ? C12 C11 S1 110.2(4) . . ? C10 C11 S1 119.4(4) . . ? C11 C12 C13 111.9(5) . . ? C11 C12 H12 124.1 . . ? C13 C12 H12 124.1 . . ? C14 C13 C12 113.0(6) . . ? C14 C13 H13 123.5 . . ? C12 C13 H13 123.5 . . ? C13 C14 S1 113.6(5) . . ? C13 C14 H14 123.2 . . ? S1 C14 H14 123.2 . . ? O10 C15 C16 106.6(5) . . ? O10 C15 H15A 110.4 . . ? C16 C15 H15A 110.4 . . ? O10 C15 H15B 110.4 . . ? C16 C15 H15B 110.4 . . ? H15A C15 H15B 108.6 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 Re1 Re2 C9 -51.7(2) . . . . ? C2 Re1 Re2 C9 125.7(2) . . . . ? C5 Re1 Re2 C9 37.3(2) . . . . ? C3 Re1 Re2 C9 -143.1(2) . . . . ? C4 Re1 Re2 C8 32.9(2) . . . . ? C2 Re1 Re2 C8 -149.7(2) . . . . ? C5 Re1 Re2 C8 122.0(2) . . . . ? C3 Re1 Re2 C8 -58.5(2) . . . . ? C4 Re1 Re2 C7 115.3(2) . . . . ? C2 Re1 Re2 C7 -67.2(2) . . . . ? C5 Re1 Re2 C7 -155.6(2) . . . . ? C3 Re1 Re2 C7 23.9(2) . . . . ? C4 Re1 Re2 C10 -146.9(2) . . . . ? C2 Re1 Re2 C10 30.6(2) . . . . ? C5 Re1 Re2 C10 -57.8(2) . . . . ? C3 Re1 Re2 C10 121.8(2) . . . . ? C6 Re2 C10 O10 95.7(5) . . . . ? C9 Re2 C10 O10 -170.5(5) . . . . ? C7 Re2 C10 O10 3.2(5) . . . . ? Re1 Re2 C10 O10 -88.3(5) . . . . ? C6 Re2 C10 C11 -87.3(5) . . . . ? C9 Re2 C10 C11 6.5(5) . . . . ? C7 Re2 C10 C11 -179.8(5) . . . . ? Re1 Re2 C10 C11 88.7(4) . . . . ? C11 C10 O10 C15 -179.9(5) . . . . ? Re2 C10 O10 C15 -2.4(8) . . . . ? O10 C10 C11 C12 -154.7(6) . . . . ? Re2 C10 C11 C12 27.7(9) . . . . ? O10 C10 C11 S1 26.1(6) . . . . ? Re2 C10 C11 S1 -151.5(3) . . . . ? C14 S1 C11 C12 -0.8(5) . . . . ? C14 S1 C11 C10 178.6(5) . . . . ? C10 C11 C12 C13 -179.6(6) . . . . ? S1 C11 C12 C13 -0.4(7) . . . . ? C11 C12 C13 C14 1.8(9) . . . . ? C12 C13 C14 S1 -2.4(10) . . . . ? C11 S1 C14 C13 1.9(7) . . . . ? C10 O10 C15 C16 174.2(5) . . . . ? #END data_ao08_complex_2a _database_code_depnum_ccdc_archive 'CCDC 824377' #TrackingRef '- Lotz_Landman_Olivier_Bezuidenhout_Liles_Palmer.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Thiophene-2,5-bis((ethoxymethylidene)-(nonacarbonyl)-dirhenium) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H12 O20 Re4 S' _chemical_formula_sum 'C28 H12 O20 Re4 S' _chemical_formula_weight 1445.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.3975(16) _cell_length_b 12.4762(16) _cell_length_c 13.8030(18) _cell_angle_alpha 112.639(1) _cell_angle_beta 105.394(1) _cell_angle_gamma 98.378(1) _cell_volume 1824.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6812 _cell_measurement_theta_min 2.520 _cell_measurement_theta_max 26.302 _exptl_crystal_description block _exptl_crystal_colour dark-red _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas . _exptl_crystal_density_diffrn 2.631 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 13.363 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.028 _exptl_absorpt_correction_T_max 0.053 _exptl_absorpt_process_details 'SADABS (Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker (Seimens) P4' _diffrn_measurement_method '\f and \w scans' _diffrn_detector 'SMART 1000 CCD' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 9557 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 26.44 _diffrn_measured_fraction_theta_max 0.865 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.966 _reflns_number_total 6497 _reflns_number_gt 5638 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Bruker, 2001)' _computing_structure_refinement ;SHELXTL and SHELXL-97 (Sheldrick, 1997) ; _computing_molecular_graphics ; ORTEP-3 for Windows (Farrugia, 1997), POV-Ray (The POV-Ray Team, 2004) ; _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0878P)^2^+7.6057P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 6497 _refine_ls_number_parameters 480 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1321 _refine_ls_wR_factor_gt 0.1239 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 3.879 _refine_diff_density_min -2.568 _refine_diff_density_rms 0.298 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Re1 Re 0.45509(3) 0.71336(3) 0.07972(3) 0.03911(13) Uani 1 1 d . . . Re2 Re 0.61074(3) 0.93551(3) 0.29421(3) 0.04011(14) Uani 1 1 d . . . Re3 Re 1.05574(4) 0.66435(4) 0.76194(4) 0.04413(14) Uani 1 1 d . . . Re4 Re 0.82549(3) 0.69169(3) 0.79556(3) 0.03895(13) Uani 1 1 d . . . C1 C 0.3595(9) 0.5712(9) -0.0572(10) 0.049(2) Uani 1 1 d . . . O1 O 0.3065(8) 0.4898(7) -0.1396(8) 0.066(2) Uani 1 1 d . . . C2 C 0.4442(9) 0.8173(9) -0.0007(9) 0.047(2) Uani 1 1 d . . . O2 O 0.4363(9) 0.8756(8) -0.0455(8) 0.070(2) Uani 1 1 d . . . C3 C 0.3210(10) 0.7567(10) 0.1258(10) 0.052(3) Uani 1 1 d . . . O3 O 0.2470(9) 0.7827(10) 0.1502(9) 0.078(3) Uani 1 1 d . . . C4 C 0.4735(9) 0.6274(9) 0.1728(9) 0.046(2) Uani 1 1 d . . . O4 O 0.4822(7) 0.5752(8) 0.2268(8) 0.063(2) Uani 1 1 d . . . C5 C 0.6049(10) 0.6936(10) 0.0583(9) 0.049(2) Uani 1 1 d . . . O5 O 0.6881(8) 0.6825(8) 0.0421(8) 0.064(2) Uani 1 1 d . . . C6 C 0.7013(10) 0.9610(10) 0.2013(9) 0.053(3) Uani 1 1 d . . . O6 O 0.7522(9) 0.9766(9) 0.1487(9) 0.085(3) Uani 1 1 d . . . C7 C 0.4952(11) 1.0126(9) 0.2392(10) 0.054(3) Uani 1 1 d . . . O7 O 0.4284(9) 1.0572(8) 0.2081(8) 0.077(3) Uani 1 1 d . . . C8 C 0.5096(10) 0.8866(9) 0.3692(9) 0.048(2) Uani 1 1 d . . . O8 O 0.4475(8) 0.8570(9) 0.4061(8) 0.073(2) Uani 1 1 d . . . C9 C 0.7000(11) 1.0848(11) 0.4219(11) 0.059(3) Uani 1 1 d . . . O9 O 0.7576(9) 1.1751(8) 0.4978(8) 0.079(3) Uani 1 1 d . . . C10 C 1.2013(10) 0.6447(12) 0.7379(10) 0.058(3) Uani 1 1 d . . . O10 O 1.2835(8) 0.6332(10) 0.7222(9) 0.076(3) Uani 1 1 d . . . C11 C 0.9607(10) 0.5168(10) 0.6210(11) 0.057(3) Uani 1 1 d . . . O11 O 0.9084(10) 0.4355(8) 0.5410(9) 0.088(4) Uani 1 1 d . . . C12 C 1.0618(11) 0.5718(12) 0.8509(11) 0.062(3) Uani 1 1 d . . . O12 O 1.0628(10) 0.5175(11) 0.9030(11) 0.093(3) Uani 1 1 d . . . C13 C 1.1358(9) 0.8160(10) 0.9061(10) 0.047(2) Uani 1 1 d . . . O13 O 1.1803(8) 0.8992(8) 0.9859(7) 0.069(2) Uani 1 1 d . . . C14 C 1.0340(9) 0.7608(11) 0.6769(9) 0.049(2) Uani 1 1 d . . . O14 O 1.0267(8) 0.8202(9) 0.6319(8) 0.073(2) Uani 1 1 d . . . C15 C 0.7949(10) 0.5272(10) 0.7853(10) 0.053(3) Uani 1 1 d . . . O15 O 0.7858(9) 0.4392(9) 0.7939(10) 0.084(3) Uani 1 1 d . . . C16 C 0.9150(10) 0.7411(12) 0.9562(10) 0.057(3) Uani 1 1 d . . . O16 O 0.9653(10) 0.7642(10) 1.0452(8) 0.085(3) Uani 1 1 d . . . C17 C 0.8964(11) 0.8619(10) 0.8299(10) 0.053(3) Uani 1 1 d . . . O17 O 0.9442(9) 0.9589(7) 0.8597(8) 0.075(3) Uani 1 1 d . . . C18 C 0.6841(10) 0.7190(11) 0.8235(9) 0.051(3) Uani 1 1 d . . . O18 O 0.6010(9) 0.7311(10) 0.8387(9) 0.080(3) Uani 1 1 d . . . C19 C 0.7277(9) 0.8467(9) 0.3465(8) 0.043(2) Uani 1 1 d . . . O19 O 0.8028(7) 0.8203(8) 0.2968(7) 0.064(2) Uani 1 1 d . . . C20 C 0.7448(8) 0.6425(8) 0.6264(8) 0.038(2) Uani 1 1 d . . . O20 O 0.6831(7) 0.5352(6) 0.5397(6) 0.0488(17) Uani 1 1 d . . . S1 S 0.7395(2) 0.6793(2) 0.4384(2) 0.0446(5) Uani 1 1 d . . . C21 C 0.7338(8) 0.8191(9) 0.4422(8) 0.041(2) Uani 1 1 d . . . C22 C 0.7323(9) 0.8953(8) 0.5436(9) 0.046(2) Uani 1 1 d . . . H22 H 0.7274 0.9738 0.5614 0.055 Uiso 1 1 calc R . . C23 C 0.7388(9) 0.8434(9) 0.6196(9) 0.044(2) Uani 1 1 d . . . H23 H 0.7387 0.8847 0.6919 0.053 Uiso 1 1 calc R . . C24 C 0.7450(8) 0.7285(8) 0.5766(8) 0.040(2) Uani 1 1 d . . . C25 C 0.9087(11) 0.7900(15) 0.3417(13) 0.075(4) Uani 1 1 d . . . H25A H 0.9343 0.8269 0.4229 0.090 Uiso 1 1 calc R . . H25B H 0.8924 0.7031 0.3146 0.090 Uiso 1 1 calc R . . C26 C 0.9961(16) 0.831(3) 0.309(2) 0.155(11) Uani 1 1 d . . . H26A H 0.9663 0.8052 0.2293 0.232 Uiso 1 1 calc R . . H26B H 1.0600 0.7986 0.3271 0.232 Uiso 1 1 calc R . . H26C H 1.0224 0.9177 0.3472 0.232 Uiso 1 1 calc R . . C27 C 0.6472(11) 0.4294(11) 0.5544(11) 0.057(3) Uani 1 1 d . . . H27A H 0.6102 0.4470 0.6104 0.068 Uiso 1 1 calc R . . H27B H 0.7138 0.4015 0.5786 0.068 Uiso 1 1 calc R . . C28 C 0.5620(11) 0.3346(10) 0.4417(11) 0.066(3) Uani 1 1 d . . . H28A H 0.6022 0.3105 0.3897 0.099 Uiso 1 1 calc R . . H28B H 0.5020 0.3674 0.4144 0.099 Uiso 1 1 calc R . . H28C H 0.5276 0.2656 0.4494 0.099 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Re1 0.0397(2) 0.0359(2) 0.0442(3) 0.02266(18) 0.01151(18) 0.00952(16) Re2 0.0454(2) 0.0349(2) 0.0427(2) 0.02384(18) 0.01075(18) 0.00910(16) Re3 0.0410(2) 0.0496(2) 0.0471(3) 0.0247(2) 0.01852(19) 0.01270(18) Re4 0.0412(2) 0.0448(2) 0.0414(2) 0.02720(19) 0.01667(18) 0.01465(17) C1 0.045(6) 0.040(5) 0.055(7) 0.023(5) 0.007(5) 0.008(5) O1 0.074(6) 0.044(4) 0.056(5) 0.014(4) 0.004(4) 0.010(4) C2 0.042(5) 0.046(5) 0.047(6) 0.018(5) 0.009(5) 0.014(4) O2 0.086(6) 0.064(5) 0.084(6) 0.058(5) 0.024(5) 0.022(4) C3 0.045(6) 0.048(6) 0.058(7) 0.027(5) 0.009(5) 0.012(5) O3 0.067(6) 0.103(7) 0.108(8) 0.072(7) 0.047(6) 0.046(6) C4 0.037(5) 0.051(6) 0.049(6) 0.021(5) 0.012(4) 0.014(4) O4 0.063(5) 0.068(5) 0.072(6) 0.053(5) 0.016(4) 0.009(4) C5 0.052(6) 0.054(6) 0.056(7) 0.035(5) 0.023(5) 0.020(5) O5 0.060(5) 0.079(6) 0.079(6) 0.051(5) 0.033(5) 0.033(4) C6 0.054(6) 0.049(6) 0.049(6) 0.028(5) 0.004(5) -0.003(5) O6 0.089(7) 0.088(7) 0.094(7) 0.063(6) 0.036(6) 0.003(5) C7 0.070(7) 0.034(5) 0.052(6) 0.018(5) 0.016(6) 0.014(5) O7 0.095(7) 0.061(5) 0.082(7) 0.039(5) 0.015(5) 0.045(5) C8 0.056(6) 0.050(6) 0.039(5) 0.021(5) 0.016(5) 0.013(5) O8 0.074(6) 0.092(7) 0.066(6) 0.040(5) 0.041(5) 0.017(5) C9 0.063(7) 0.055(7) 0.067(8) 0.042(7) 0.013(6) 0.021(6) O9 0.077(6) 0.044(4) 0.063(6) 0.000(4) -0.009(5) -0.003(4) C10 0.045(6) 0.083(8) 0.055(7) 0.034(6) 0.024(5) 0.024(6) O10 0.056(5) 0.111(8) 0.087(7) 0.054(6) 0.044(5) 0.037(5) C11 0.049(6) 0.050(6) 0.072(8) 0.027(6) 0.027(6) -0.001(5) O11 0.102(8) 0.057(5) 0.069(6) -0.005(5) 0.044(6) -0.015(5) C12 0.057(7) 0.073(8) 0.068(8) 0.035(7) 0.028(6) 0.030(6) O12 0.099(8) 0.117(9) 0.119(10) 0.092(8) 0.051(7) 0.049(7) C13 0.044(5) 0.056(6) 0.051(7) 0.038(6) 0.015(5) 0.007(5) O13 0.069(6) 0.063(5) 0.048(5) 0.015(4) 0.004(4) 0.000(4) C14 0.043(6) 0.063(7) 0.040(6) 0.024(5) 0.010(4) 0.015(5) O14 0.071(6) 0.089(6) 0.076(6) 0.061(6) 0.022(5) 0.014(5) C15 0.056(6) 0.060(6) 0.052(7) 0.039(6) 0.013(5) 0.016(5) O15 0.079(6) 0.070(6) 0.109(8) 0.066(6) 0.010(6) 0.008(5) C16 0.053(6) 0.074(8) 0.055(7) 0.043(6) 0.014(6) 0.016(6) O16 0.092(7) 0.102(8) 0.051(6) 0.038(5) 0.011(5) 0.017(6) C17 0.061(7) 0.046(6) 0.053(7) 0.022(5) 0.020(5) 0.018(5) O17 0.088(7) 0.045(5) 0.082(7) 0.026(5) 0.020(5) 0.013(4) C18 0.051(6) 0.071(7) 0.054(6) 0.042(6) 0.023(5) 0.028(5) O18 0.078(6) 0.136(9) 0.097(8) 0.091(7) 0.057(6) 0.066(6) C19 0.043(5) 0.041(5) 0.041(5) 0.023(4) 0.008(4) 0.004(4) O19 0.058(5) 0.087(6) 0.068(6) 0.046(5) 0.031(4) 0.029(4) C20 0.034(5) 0.035(4) 0.052(6) 0.027(4) 0.016(4) 0.010(4) O20 0.055(4) 0.037(3) 0.053(4) 0.023(3) 0.017(3) 0.006(3) S1 0.0584(15) 0.0376(12) 0.0414(13) 0.0221(10) 0.0158(11) 0.0136(10) C21 0.038(5) 0.042(5) 0.044(6) 0.024(4) 0.011(4) 0.012(4) C22 0.060(6) 0.032(4) 0.049(6) 0.024(4) 0.016(5) 0.013(4) C23 0.050(6) 0.045(5) 0.046(6) 0.025(5) 0.016(5) 0.022(4) C24 0.038(5) 0.036(5) 0.043(5) 0.021(4) 0.007(4) 0.009(4) C25 0.056(7) 0.103(11) 0.087(10) 0.055(9) 0.028(7) 0.035(7) C26 0.073(11) 0.32(3) 0.17(2) 0.18(2) 0.060(13) 0.076(17) C27 0.063(7) 0.058(7) 0.065(8) 0.038(6) 0.027(6) 0.020(6) C28 0.057(7) 0.047(6) 0.072(8) 0.018(6) 0.014(6) -0.004(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 C1 1.934(11) . ? Re1 C4 1.956(11) . ? Re1 C5 1.992(11) . ? Re1 C2 2.003(11) . ? Re1 C3 2.005(12) . ? Re1 Re2 3.0434(6) . ? Re2 C9 1.907(13) . ? Re2 C7 1.984(12) . ? Re2 C8 1.992(11) . ? Re2 C6 1.995(12) . ? Re2 C19 2.093(10) . ? Re3 C10 1.952(11) . ? Re3 C12 1.978(14) . ? Re3 C14 1.978(12) . ? Re3 C11 1.989(13) . ? Re3 C13 2.008(12) . ? Re3 Re4 3.0569(7) . ? Re4 C18 1.942(11) . ? Re4 C15 1.975(11) . ? Re4 C17 1.991(12) . ? Re4 C16 1.993(12) . ? Re4 C20 2.076(10) . ? C1 O1 1.129(13) . ? C2 O2 1.121(13) . ? C3 O3 1.108(14) . ? C4 O4 1.159(13) . ? C5 O5 1.128(13) . ? C6 O6 1.131(14) . ? C7 O7 1.144(14) . ? C8 O8 1.123(13) . ? C9 O9 1.156(14) . ? C10 O10 1.114(13) . ? C11 O11 1.111(15) . ? C12 O12 1.162(16) . ? C13 O13 1.107(13) . ? C14 O14 1.135(14) . ? C15 O15 1.142(13) . ? C16 O16 1.117(14) . ? C17 O17 1.125(14) . ? C18 O18 1.124(13) . ? C19 O19 1.303(13) . ? C19 C21 1.476(14) . ? O19 C25 1.465(15) . ? C20 O20 1.338(12) . ? C20 C24 1.480(12) . ? O20 C27 1.438(13) . ? S1 C21 1.736(10) . ? S1 C24 1.744(10) . ? C21 C22 1.363(14) . ? C22 C23 1.421(14) . ? C22 H22 0.9300 . ? C23 C24 1.347(13) . ? C23 H23 0.9300 . ? C25 C26 1.39(2) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C28 1.511(17) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Re1 C4 94.6(4) . . ? C1 Re1 C5 94.6(5) . . ? C4 Re1 C5 90.1(4) . . ? C1 Re1 C2 91.3(4) . . ? C4 Re1 C2 174.0(4) . . ? C5 Re1 C2 90.3(4) . . ? C1 Re1 C3 94.9(5) . . ? C4 Re1 C3 88.5(4) . . ? C5 Re1 C3 170.4(5) . . ? C2 Re1 C3 90.1(4) . . ? C1 Re1 Re2 178.6(3) . . ? C4 Re1 Re2 85.2(3) . . ? C5 Re1 Re2 84.0(3) . . ? C2 Re1 Re2 88.9(3) . . ? C3 Re1 Re2 86.4(3) . . ? C9 Re2 C7 91.7(5) . . ? C9 Re2 C8 94.6(5) . . ? C7 Re2 C8 89.3(5) . . ? C9 Re2 C6 93.4(5) . . ? C7 Re2 C6 91.6(5) . . ? C8 Re2 C6 171.9(4) . . ? C9 Re2 C19 90.8(4) . . ? C7 Re2 C19 177.4(4) . . ? C8 Re2 C19 90.2(4) . . ? C6 Re2 C19 88.5(4) . . ? C9 Re2 Re1 173.8(3) . . ? C7 Re2 Re1 82.3(3) . . ? C8 Re2 Re1 86.9(3) . . ? C6 Re2 Re1 85.2(3) . . ? C19 Re2 Re1 95.2(3) . . ? C10 Re3 C12 94.4(5) . . ? C10 Re3 C14 92.0(5) . . ? C12 Re3 C14 173.5(5) . . ? C10 Re3 C11 92.6(5) . . ? C12 Re3 C11 91.5(5) . . ? C14 Re3 C11 88.8(5) . . ? C10 Re3 C13 93.4(5) . . ? C12 Re3 C13 88.5(5) . . ? C14 Re3 C13 90.6(4) . . ? C11 Re3 C13 174.0(4) . . ? C10 Re3 Re4 179.0(4) . . ? C12 Re3 Re4 85.8(3) . . ? C14 Re3 Re4 87.8(3) . . ? C11 Re3 Re4 86.4(3) . . ? C13 Re3 Re4 87.6(3) . . ? C18 Re4 C15 94.4(5) . . ? C18 Re4 C17 95.7(5) . . ? C15 Re4 C17 165.6(5) . . ? C18 Re4 C16 93.6(5) . . ? C15 Re4 C16 83.9(5) . . ? C17 Re4 C16 85.2(5) . . ? C18 Re4 C20 90.7(4) . . ? C15 Re4 C20 97.2(4) . . ? C17 Re4 C20 92.9(4) . . ? C16 Re4 C20 175.5(4) . . ? C18 Re4 Re3 176.6(4) . . ? C15 Re4 Re3 88.2(3) . . ? C17 Re4 Re3 81.4(3) . . ? C16 Re4 Re3 84.5(3) . . ? C20 Re4 Re3 91.2(2) . . ? O1 C1 Re1 176.9(11) . . ? O2 C2 Re1 178.8(10) . . ? O3 C3 Re1 178.2(10) . . ? O4 C4 Re1 178.7(10) . . ? O5 C5 Re1 177.2(10) . . ? O6 C6 Re2 179.2(11) . . ? O7 C7 Re2 179.5(11) . . ? O8 C8 Re2 176.2(10) . . ? O9 C9 Re2 177.3(12) . . ? O10 C10 Re3 178.7(11) . . ? O11 C11 Re3 178.6(11) . . ? O12 C12 Re3 178.4(11) . . ? O13 C13 Re3 179.5(11) . . ? O14 C14 Re3 176.5(10) . . ? O15 C15 Re4 171.1(11) . . ? O16 C16 Re4 177.3(12) . . ? O17 C17 Re4 172.6(11) . . ? O18 C18 Re4 177.9(11) . . ? O19 C19 C21 118.2(9) . . ? O19 C19 Re2 119.1(7) . . ? C21 C19 Re2 122.7(7) . . ? C19 O19 C25 125.2(10) . . ? O20 C20 C24 104.5(8) . . ? O20 C20 Re4 131.5(6) . . ? C24 C20 Re4 124.1(7) . . ? C20 O20 C27 122.3(8) . . ? C21 S1 C24 92.0(5) . . ? C22 C21 C19 126.3(9) . . ? C22 C21 S1 110.1(7) . . ? C19 C21 S1 123.6(7) . . ? C21 C22 C23 113.7(9) . . ? C21 C22 H22 123.1 . . ? C23 C22 H22 123.1 . . ? C24 C23 C22 113.3(9) . . ? C24 C23 H23 123.3 . . ? C22 C23 H23 123.3 . . ? C23 C24 C20 129.2(9) . . ? C23 C24 S1 110.8(7) . . ? C20 C24 S1 119.7(7) . . ? C26 C25 O19 110.2(14) . . ? C26 C25 H25A 109.6 . . ? O19 C25 H25A 109.6 . . ? C26 C25 H25B 109.6 . . ? O19 C25 H25B 109.6 . . ? H25A C25 H25B 108.1 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O20 C27 C28 106.3(10) . . ? O20 C27 H27A 110.5 . . ? C28 C27 H27A 110.5 . . ? O20 C27 H27B 110.5 . . ? C28 C27 H27B 110.5 . . ? H27A C27 H27B 108.7 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 Re1 Re2 C7 -136.9(5) . . . . ? C5 Re1 Re2 C7 132.5(5) . . . . ? C2 Re1 Re2 C7 42.1(5) . . . . ? C3 Re1 Re2 C7 -48.1(5) . . . . ? C4 Re1 Re2 C8 -47.2(4) . . . . ? C5 Re1 Re2 C8 -137.9(4) . . . . ? C2 Re1 Re2 C8 131.7(4) . . . . ? C3 Re1 Re2 C8 41.5(5) . . . . ? C4 Re1 Re2 C6 130.8(4) . . . . ? C5 Re1 Re2 C6 40.1(4) . . . . ? C2 Re1 Re2 C6 -50.3(4) . . . . ? C3 Re1 Re2 C6 -140.5(5) . . . . ? C4 Re1 Re2 C19 42.7(4) . . . . ? C5 Re1 Re2 C19 -47.9(4) . . . . ? C2 Re1 Re2 C19 -138.3(4) . . . . ? C3 Re1 Re2 C19 131.5(4) . . . . ? C12 Re3 Re4 C15 -35.5(5) . . . . ? C14 Re3 Re4 C15 145.2(5) . . . . ? C11 Re3 Re4 C15 56.3(5) . . . . ? C13 Re3 Re4 C15 -124.1(4) . . . . ? C12 Re3 Re4 C17 134.5(5) . . . . ? C14 Re3 Re4 C17 -44.8(5) . . . . ? C11 Re3 Re4 C17 -133.7(5) . . . . ? C13 Re3 Re4 C17 45.9(4) . . . . ? C12 Re3 Re4 C16 48.6(5) . . . . ? C14 Re3 Re4 C16 -130.8(5) . . . . ? C11 Re3 Re4 C16 140.3(5) . . . . ? C13 Re3 Re4 C16 -40.1(4) . . . . ? C12 Re3 Re4 C20 -132.7(5) . . . . ? C14 Re3 Re4 C20 48.0(4) . . . . ? C11 Re3 Re4 C20 -40.9(4) . . . . ? C13 Re3 Re4 C20 138.7(4) . . . . ? C9 Re2 C19 O19 -103.2(9) . . . . ? C8 Re2 C19 O19 162.2(8) . . . . ? C6 Re2 C19 O19 -9.8(8) . . . . ? Re1 Re2 C19 O19 75.2(8) . . . . ? C9 Re2 C19 C21 73.0(8) . . . . ? C8 Re2 C19 C21 -21.6(8) . . . . ? C6 Re2 C19 C21 166.4(8) . . . . ? Re1 Re2 C19 C21 -108.5(7) . . . . ? C21 C19 O19 C25 -14.2(16) . . . . ? Re2 C19 O19 C25 162.1(10) . . . . ? C18 Re4 C20 O20 -89.5(9) . . . . ? C15 Re4 C20 O20 5.1(9) . . . . ? C17 Re4 C20 O20 174.8(9) . . . . ? Re3 Re4 C20 O20 93.4(8) . . . . ? C18 Re4 C20 C24 90.0(8) . . . . ? C15 Re4 C20 C24 -175.4(8) . . . . ? C17 Re4 C20 C24 -5.7(8) . . . . ? Re3 Re4 C20 C24 -87.1(7) . . . . ? C24 C20 O20 C27 -170.5(9) . . . . ? Re4 C20 O20 C27 9.0(14) . . . . ? O19 C19 C21 C22 132.1(11) . . . . ? Re2 C19 C21 C22 -44.2(14) . . . . ? O19 C19 C21 S1 -50.1(13) . . . . ? Re2 C19 C21 S1 133.6(7) . . . . ? C24 S1 C21 C22 -2.0(8) . . . . ? C24 S1 C21 C19 179.8(9) . . . . ? C19 C21 C22 C23 179.7(10) . . . . ? S1 C21 C22 C23 1.6(12) . . . . ? C21 C22 C23 C24 -0.2(14) . . . . ? C22 C23 C24 C20 -175.4(10) . . . . ? C22 C23 C24 S1 -1.4(11) . . . . ? O20 C20 C24 C23 142.9(11) . . . . ? Re4 C20 C24 C23 -36.7(14) . . . . ? O20 C20 C24 S1 -30.6(10) . . . . ? Re4 C20 C24 S1 149.8(5) . . . . ? C21 S1 C24 C23 2.0(8) . . . . ? C21 S1 C24 C20 176.6(8) . . . . ? C19 O19 C25 C26 -146.9(17) . . . . ? C20 O20 C27 C28 169.6(9) . . . . ? #END data_ao04_complex_5b _database_code_depnum_ccdc_archive 'CCDC 824378' #TrackingRef '- Lotz_Landman_Olivier_Bezuidenhout_Liles_Palmer.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Nonacarbonyl-(ethoxy-(2,2'-bis(thien-4-yl)-4'-aldehyde)-methylidene)-dirhenium ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H10 O11 Re2 S2' _chemical_formula_sum 'C21 H10 O11 Re2 S2' _chemical_formula_weight 874.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.5208(8) _cell_length_b 13.1481(11) _cell_length_c 20.6062(17) _cell_angle_alpha 90.00 _cell_angle_beta 101.041(1) _cell_angle_gamma 90.00 _cell_volume 2531.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5207 _cell_measurement_theta_min 2.570 _cell_measurement_theta_max 26.403 _exptl_crystal_description irregular-fragment _exptl_crystal_colour dark-red _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas . _exptl_crystal_density_diffrn 2.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1624 _exptl_absorpt_coefficient_mu 9.775 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.062 _exptl_absorpt_correction_T_max 0.087 _exptl_absorpt_process_details 'SADABS (Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker (Seimens) P4' _diffrn_measurement_method '\f and \w scans' _diffrn_detector 'SMART 1000 CCD' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 13364 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 26.47 _diffrn_measured_fraction_theta_max 0.920 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _reflns_number_total 4809 _reflns_number_gt 4475 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Bruker, 2001)' _computing_structure_refinement ;SHELXTL and SHELXL-97 (Sheldrick, 1997) ; _computing_molecular_graphics ; ORTEP-3 for Windows (Farrugia, 1997), POV-Ray (Cason, 2004) ; _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger All H atoms were constrained to ride on the atom to which they are bonded with isotropic displacement parameters set to 1.2 times the eqivalent isotropic displacemnt parameter of the atom to which thay are bonded (1.5 times for the methyl Hs).. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0325P)^2^+1.2828P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 4809 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0266 _refine_ls_R_factor_gt 0.0244 _refine_ls_wR_factor_ref 0.0637 _refine_ls_wR_factor_gt 0.0623 _refine_ls_goodness_of_fit_ref 1.165 _refine_ls_restrained_S_all 1.165 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.774 _refine_diff_density_min -0.932 _refine_diff_density_rms 0.135 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Re1 Re 0.827656(17) 0.195631(13) 0.308527(8) 0.04221(7) Uani 1 1 d . . . Re2 Re 1.110286(17) 0.246187(12) 0.264041(7) 0.03927(7) Uani 1 1 d . . . C1 C 0.6449(5) 0.1724(4) 0.3339(2) 0.0547(11) Uani 1 1 d . . . O1 O 0.5370(4) 0.1565(4) 0.34843(18) 0.0747(11) Uani 1 1 d . . . C2 C 0.7353(5) 0.2602(4) 0.2236(2) 0.0539(12) Uani 1 1 d . . . O2 O 0.6814(4) 0.2946(4) 0.1753(2) 0.0795(12) Uani 1 1 d . . . C3 C 0.8656(5) 0.3289(4) 0.3534(2) 0.0539(11) Uani 1 1 d . . . O3 O 0.8919(5) 0.4045(3) 0.3804(2) 0.0795(11) Uani 1 1 d . . . C4 C 0.9360(5) 0.1290(4) 0.3902(3) 0.0612(12) Uani 1 1 d . . . O4 O 0.9953(5) 0.0921(4) 0.4367(2) 0.1023(16) Uani 1 1 d . . . C5 C 0.8261(6) 0.0640(4) 0.2611(3) 0.0626(13) Uani 1 1 d . . . O5 O 0.8283(6) -0.0123(3) 0.2356(2) 0.0986(15) Uani 1 1 d . . . C6 C 1.2932(5) 0.2676(4) 0.2404(3) 0.0607(13) Uani 1 1 d . . . O6 O 1.4029(5) 0.2808(5) 0.2273(2) 0.0979(16) Uani 1 1 d . . . C7 C 1.0703(5) 0.3950(4) 0.2658(2) 0.0511(10) Uani 1 1 d . . . O7 O 1.0585(5) 0.4786(3) 0.27526(19) 0.0749(10) Uani 1 1 d . . . C8 C 1.1840(6) 0.2622(4) 0.3600(2) 0.0553(12) Uani 1 1 d . . . O8 O 1.2274(5) 0.2711(4) 0.41473(18) 0.0877(14) Uani 1 1 d . . . C9 C 1.1450(5) 0.1002(4) 0.2820(2) 0.0547(11) Uani 1 1 d . . . O9 O 1.1717(5) 0.0178(3) 0.29951(19) 0.0846(12) Uani 1 1 d . . . C10 C 1.0086(5) 0.2219(4) 0.1646(2) 0.0429(9) Uani 1 1 d . . . O10 O 0.9459(4) 0.2864(2) 0.11875(15) 0.0525(8) Uani 1 1 d . . . C11 C 0.9859(4) 0.1226(3) 0.13254(18) 0.0430(9) Uani 1 1 d . . . C12 C 1.0700(5) 0.0369(4) 0.1405(2) 0.0542(11) Uani 1 1 d . . . H12 H 1.1556 0.0323 0.1708 0.065 Uiso 1 1 calc R . . C13 C 1.0142(5) -0.0430(4) 0.0983(2) 0.0578(12) Uani 1 1 d . . . H13 H 1.0597 -0.1054 0.0978 0.069 Uiso 1 1 calc R . . C14 C 0.8871(4) -0.0205(3) 0.05825(19) 0.0446(9) Uani 1 1 d . . . S1 S 0.83785(12) 0.10259(9) 0.07009(5) 0.0486(2) Uani 1 1 d . . . C15 C 0.7968(5) -0.0870(3) 0.01161(19) 0.0472(10) Uani 1 1 d . . . C16 C 0.6710(5) -0.0652(4) -0.0306(2) 0.0633(13) Uani 1 1 d . . . H16 H 0.6305 -0.0006 -0.0355 0.076 Uiso 1 1 calc R . . C17 C 0.6105(6) -0.1499(5) -0.0653(3) 0.0705(14) Uani 1 1 d . . . H17 H 0.5239 -0.1480 -0.0952 0.085 Uiso 1 1 calc R . . C18 C 0.6909(6) -0.2367(4) -0.0512(2) 0.0573(12) Uani 1 1 d . . . S2 S 0.84296(14) -0.21208(10) 0.00607(6) 0.0546(3) Uani 1 1 d . . . C19 C 0.9460(6) 0.3958(4) 0.1249(3) 0.0609(12) Uani 1 1 d . . . H19A H 1.0432 0.4216 0.1351 0.073 Uiso 1 1 calc R . . H19B H 0.8965 0.4165 0.1598 0.073 Uiso 1 1 calc R . . C20 C 0.8689(9) 0.4354(5) 0.0586(3) 0.109(3) Uani 1 1 d . . . H20A H 0.9240 0.4198 0.0254 0.164 Uiso 1 1 calc R . . H20B H 0.8572 0.5077 0.0611 0.164 Uiso 1 1 calc R . . H20C H 0.7766 0.4037 0.0473 0.164 Uiso 1 1 calc R . . O11 O 0.7447(6) -0.4084(3) -0.0620(2) 0.0926(13) Uani 1 1 d . . . C21 C 0.6633(7) -0.3400(5) -0.0759(3) 0.0698(14) Uani 1 1 d . . . H21 H 0.5767 -0.3531 -0.1041 0.084 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Re1 0.03752(11) 0.04603(11) 0.04415(10) -0.00016(7) 0.01055(7) -0.00311(7) Re2 0.03343(11) 0.04734(12) 0.03694(10) 0.00149(6) 0.00653(7) -0.00024(6) C1 0.050(3) 0.068(3) 0.048(2) 0.004(2) 0.012(2) -0.009(2) O1 0.050(2) 0.108(3) 0.070(2) 0.008(2) 0.0210(18) -0.013(2) C2 0.038(3) 0.073(3) 0.050(3) -0.001(2) 0.006(2) -0.003(2) O2 0.056(2) 0.122(4) 0.059(2) 0.025(2) 0.0060(19) 0.006(2) C3 0.052(3) 0.061(3) 0.053(2) -0.004(2) 0.021(2) 0.003(2) O3 0.088(3) 0.069(2) 0.089(3) -0.034(2) 0.036(2) -0.013(2) C4 0.054(3) 0.069(3) 0.063(3) 0.016(3) 0.018(2) 0.004(2) O4 0.095(3) 0.129(4) 0.081(3) 0.045(3) 0.011(2) 0.019(3) C5 0.063(3) 0.057(3) 0.071(3) -0.005(2) 0.020(3) -0.019(2) O5 0.127(4) 0.057(2) 0.120(3) -0.034(2) 0.045(3) -0.031(2) C6 0.042(3) 0.084(4) 0.056(3) 0.020(3) 0.010(2) 0.003(2) O6 0.050(3) 0.152(4) 0.096(3) 0.044(3) 0.027(2) 0.008(3) C7 0.049(2) 0.054(3) 0.051(2) -0.002(2) 0.0118(19) 0.001(2) O7 0.094(3) 0.052(2) 0.080(2) -0.0051(18) 0.019(2) -0.003(2) C8 0.053(3) 0.065(3) 0.048(3) 0.001(2) 0.009(2) -0.011(2) O8 0.091(3) 0.119(3) 0.045(2) -0.007(2) -0.005(2) -0.035(3) C9 0.057(3) 0.060(3) 0.047(2) -0.001(2) 0.009(2) 0.006(2) O9 0.123(4) 0.057(2) 0.077(2) 0.020(2) 0.027(2) 0.037(2) C10 0.040(2) 0.050(2) 0.041(2) 0.0039(18) 0.0134(18) 0.0015(19) O10 0.062(2) 0.0470(16) 0.0454(16) 0.0087(14) 0.0021(15) 0.0037(15) C11 0.039(2) 0.055(2) 0.0355(18) 0.0014(17) 0.0076(16) 0.0037(18) C12 0.044(2) 0.068(3) 0.046(2) -0.011(2) -0.0023(19) 0.015(2) C13 0.059(3) 0.058(3) 0.054(2) -0.011(2) 0.005(2) 0.015(2) C14 0.045(2) 0.050(2) 0.0399(18) -0.0024(17) 0.0111(17) 0.0044(19) S1 0.0486(6) 0.0488(6) 0.0449(5) 0.0014(5) -0.0003(4) 0.0055(5) C15 0.051(2) 0.052(2) 0.0399(19) -0.0015(18) 0.0116(18) 0.002(2) C16 0.058(3) 0.065(3) 0.061(3) -0.007(2) -0.002(2) 0.008(2) C17 0.058(3) 0.080(4) 0.066(3) -0.005(3) -0.008(2) 0.004(3) C18 0.061(3) 0.064(3) 0.044(2) -0.005(2) 0.003(2) -0.010(2) S2 0.0607(8) 0.0552(7) 0.0456(5) -0.0025(5) 0.0042(5) 0.0025(5) C19 0.069(3) 0.045(2) 0.066(3) 0.008(2) 0.006(2) 0.000(2) C20 0.177(8) 0.066(4) 0.069(4) 0.022(3) -0.016(4) 0.018(4) O11 0.115(4) 0.064(3) 0.088(3) -0.002(2) -0.007(3) 0.000(3) C21 0.087(4) 0.066(3) 0.052(3) -0.001(2) 0.003(3) -0.013(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 C1 1.934(5) . ? Re1 C3 1.982(5) . ? Re1 C5 1.986(5) . ? Re1 C2 1.992(5) . ? Re1 C4 2.001(5) . ? Re1 Re2 3.0770(3) . ? Re2 C6 1.917(5) . ? Re2 C9 1.971(5) . ? Re2 C8 1.978(5) . ? Re2 C7 1.995(5) . ? Re2 C10 2.117(4) . ? C1 O1 1.144(6) . ? C2 O2 1.123(6) . ? C3 O3 1.143(6) . ? C4 O4 1.125(6) . ? C5 O5 1.134(6) . ? C6 O6 1.141(6) . ? C7 O7 1.126(6) . ? C8 O8 1.131(6) . ? C9 O9 1.154(6) . ? C10 O10 1.323(5) . ? C10 C11 1.460(6) . ? O10 C19 1.445(6) . ? C11 C12 1.373(6) . ? C11 S1 1.737(4) . ? C12 C13 1.400(7) . ? C12 H12 0.9300 . ? C13 C14 1.360(6) . ? C13 H13 0.9300 . ? C14 C15 1.453(6) . ? C14 S1 1.716(4) . ? C15 C16 1.370(6) . ? C15 S2 1.712(5) . ? C16 C17 1.387(7) . ? C16 H16 0.9300 . ? C17 C18 1.374(8) . ? C17 H17 0.9300 . ? C18 C21 1.456(7) . ? C18 S2 1.715(5) . ? C19 C20 1.513(7) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? O11 C21 1.186(7) . ? C21 H21 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Re1 C3 96.1(2) . . ? C1 Re1 C5 94.2(2) . . ? C3 Re1 C5 169.6(2) . . ? C1 Re1 C2 92.1(2) . . ? C3 Re1 C2 92.5(2) . . ? C5 Re1 C2 88.8(2) . . ? C1 Re1 C4 92.8(2) . . ? C3 Re1 C4 88.6(2) . . ? C5 Re1 C4 89.2(2) . . ? C2 Re1 C4 174.9(2) . . ? C1 Re1 Re2 176.16(15) . . ? C3 Re1 Re2 81.74(13) . . ? C5 Re1 Re2 88.07(14) . . ? C2 Re1 Re2 84.86(14) . . ? C4 Re1 Re2 90.34(14) . . ? C6 Re2 C9 93.6(2) . . ? C6 Re2 C8 94.2(2) . . ? C9 Re2 C8 84.4(2) . . ? C6 Re2 C7 92.6(2) . . ? C9 Re2 C7 167.90(18) . . ? C8 Re2 C7 84.8(2) . . ? C6 Re2 C10 92.6(2) . . ? C9 Re2 C10 93.65(18) . . ? C8 Re2 C10 173.05(18) . . ? C7 Re2 C10 96.42(18) . . ? C6 Re2 Re1 175.10(16) . . ? C9 Re2 Re1 81.88(14) . . ? C8 Re2 Re1 83.58(15) . . ? C7 Re2 Re1 91.49(14) . . ? C10 Re2 Re1 89.55(11) . . ? O1 C1 Re1 178.5(5) . . ? O2 C2 Re1 178.3(5) . . ? O3 C3 Re1 177.6(5) . . ? O4 C4 Re1 178.9(5) . . ? O5 C5 Re1 177.8(6) . . ? O6 C6 Re2 179.0(6) . . ? O7 C7 Re2 170.5(4) . . ? O8 C8 Re2 179.3(6) . . ? O9 C9 Re2 172.4(4) . . ? O10 C10 C11 104.1(3) . . ? O10 C10 Re2 130.9(3) . . ? C11 C10 Re2 125.0(3) . . ? C10 O10 C19 125.7(4) . . ? C12 C11 C10 130.4(4) . . ? C12 C11 S1 109.6(3) . . ? C10 C11 S1 119.9(3) . . ? C11 C12 C13 113.5(4) . . ? C11 C12 H12 123.3 . . ? C13 C12 H12 123.3 . . ? C14 C13 C12 113.7(4) . . ? C14 C13 H13 123.2 . . ? C12 C13 H13 123.2 . . ? C13 C14 C15 128.0(4) . . ? C13 C14 S1 110.7(3) . . ? C15 C14 S1 121.2(3) . . ? C14 S1 C11 92.5(2) . . ? C16 C15 C14 129.0(4) . . ? C16 C15 S2 111.3(4) . . ? C14 C15 S2 119.7(3) . . ? C15 C16 C17 112.6(5) . . ? C15 C16 H16 123.7 . . ? C17 C16 H16 123.7 . . ? C18 C17 C16 113.5(5) . . ? C18 C17 H17 123.2 . . ? C16 C17 H17 123.2 . . ? C17 C18 C21 130.2(5) . . ? C17 C18 S2 110.5(4) . . ? C21 C18 S2 119.2(4) . . ? C15 S2 C18 91.9(2) . . ? O10 C19 C20 105.7(4) . . ? O10 C19 H19A 110.6 . . ? C20 C19 H19A 110.6 . . ? O10 C19 H19B 110.6 . . ? C20 C19 H19B 110.6 . . ? H19A C19 H19B 108.7 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O11 C21 C18 123.9(6) . . ? O11 C21 H21 118.0 . . ? C18 C21 H21 118.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 Re1 Re2 C9 139.5(2) . . . . ? C5 Re1 Re2 C9 -38.3(2) . . . . ? C2 Re1 Re2 C9 -127.3(2) . . . . ? C4 Re1 Re2 C9 50.9(2) . . . . ? C3 Re1 Re2 C8 54.3(2) . . . . ? C5 Re1 Re2 C8 -123.5(2) . . . . ? C2 Re1 Re2 C8 147.5(2) . . . . ? C4 Re1 Re2 C8 -34.3(2) . . . . ? C3 Re1 Re2 C7 -30.4(2) . . . . ? C5 Re1 Re2 C7 151.8(2) . . . . ? C2 Re1 Re2 C7 62.88(19) . . . . ? C4 Re1 Re2 C7 -119.0(2) . . . . ? C3 Re1 Re2 C10 -126.80(19) . . . . ? C5 Re1 Re2 C10 55.4(2) . . . . ? C2 Re1 Re2 C10 -33.53(19) . . . . ? C4 Re1 Re2 C10 144.6(2) . . . . ? C6 Re2 C10 O10 -90.2(4) . . . . ? C9 Re2 C10 O10 176.0(4) . . . . ? C7 Re2 C10 O10 2.7(4) . . . . ? Re1 Re2 C10 O10 94.2(4) . . . . ? C6 Re2 C10 C11 93.8(4) . . . . ? C9 Re2 C10 C11 0.0(4) . . . . ? C7 Re2 C10 C11 -173.3(4) . . . . ? Re1 Re2 C10 C11 -81.9(3) . . . . ? C11 C10 O10 C19 -176.1(4) . . . . ? Re2 C10 O10 C19 7.3(7) . . . . ? O10 C10 C11 C12 147.9(5) . . . . ? Re2 C10 C11 C12 -35.2(6) . . . . ? O10 C10 C11 S1 -27.7(4) . . . . ? Re2 C10 C11 S1 149.2(2) . . . . ? C10 C11 C12 C13 -177.3(4) . . . . ? S1 C11 C12 C13 -1.4(5) . . . . ? C11 C12 C13 C14 -0.6(6) . . . . ? C12 C13 C14 C15 -176.4(4) . . . . ? C12 C13 C14 S1 2.3(5) . . . . ? C13 C14 S1 C11 -2.6(4) . . . . ? C15 C14 S1 C11 176.2(3) . . . . ? C12 C11 S1 C14 2.3(3) . . . . ? C10 C11 S1 C14 178.7(3) . . . . ? C13 C14 C15 C16 -177.8(5) . . . . ? S1 C14 C15 C16 3.7(7) . . . . ? C13 C14 C15 S2 3.7(6) . . . . ? S1 C14 C15 S2 -174.8(2) . . . . ? C14 C15 C16 C17 -176.5(4) . . . . ? S2 C15 C16 C17 2.1(6) . . . . ? C15 C16 C17 C18 -1.5(7) . . . . ? C16 C17 C18 C21 178.6(5) . . . . ? C16 C17 C18 S2 0.2(6) . . . . ? C16 C15 S2 C18 -1.7(4) . . . . ? C14 C15 S2 C18 177.1(4) . . . . ? C17 C18 S2 C15 0.8(4) . . . . ? C21 C18 S2 C15 -177.8(4) . . . . ? C10 O10 C19 C20 176.6(5) . . . . ? C17 C18 C21 O11 176.5(6) . . . . ? S2 C18 C21 O11 -5.2(8) . . . . ?