# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_DAR41b _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C18 H18 Cl N2 O3 Re, 2(C H Cl3)' _chemical_formula_sum 'C20 H20 Cl7 N2 O3 Re' _chemical_melting_point ? _exptl_crystal_description Plate _exptl_crystal_colour Green _diffrn_ambient_temperature 173(2) _chemical_formula_weight 770.73 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' N N 0.0061 0.0033 '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' Cl Cl 0.1484 0.1585 '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_int_tables_number 14 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 11.1399(17) _cell_length_b 9.4693(15) _cell_length_c 24.716(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.913(2) _cell_angle_gamma 90.00 _cell_volume 2593.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9456 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 27.4 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.974 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 5.433 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.40 _exptl_absorpt_correction_T_max 0.61 _exptl_absorpt_process_details ; Data were corrected for decay and absorption using the program SADABS (Sheldrick, G. M. (2003). SADABS. Version 2.10. University of G\"ottingen, Germany). ; _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 29273 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0164 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 27.47 _reflns_number_total 5882 _reflns_number_gt 5621 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2008)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2008)' _computing_data_reduction 'APEX2 (Bruker AXS, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-SEED, Barbour, 2001' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.0157P)^2^+2.9115P] 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 5882 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0207 _refine_ls_R_factor_gt 0.0191 _refine_ls_wR_factor_ref 0.0427 _refine_ls_wR_factor_gt 0.0422 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.116 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 0.270612(8) 0.323495(9) 0.462143(3) 0.01861(3) Uani 1 1 d . . . Cl1 Cl 0.39012(5) 0.34944(7) 0.38536(2) 0.02882(13) Uani 1 1 d . B . Cl2 Cl 0.67127(8) 0.30123(10) 0.29397(4) 0.0600(2) Uani 1 1 d . . . Cl3 Cl 0.52803(9) 0.05592(10) 0.31175(4) 0.0594(2) Uani 1 1 d . . . Cl4 Cl 0.52329(8) 0.17663(10) 0.20462(4) 0.0554(2) Uani 1 1 d . . . Cl5 Cl 0.2037(3) 0.1579(3) 0.27526(9) 0.0452(6) Uani 0.599(13) 1 d P A 1 Cl6 Cl -0.01613(19) 0.3195(7) 0.2696(2) 0.0660(14) Uani 0.599(13) 1 d P A 1 Cl7 Cl 0.2031(9) 0.4590(12) 0.2526(5) 0.0550(14) Uani 0.599(13) 1 d P A 1 O1 O 0.14615(15) 0.21909(18) 0.41354(6) 0.0232(3) Uani 1 1 d . B 2 O2 O 0.18446(14) 0.49284(17) 0.42800(6) 0.0217(3) Uani 1 1 d . B . O3 O 0.36527(16) 0.19441(18) 0.48766(7) 0.0269(4) Uani 1 1 d . B . N1 N 0.16766(17) 0.31865(19) 0.52682(7) 0.0182(4) Uani 1 1 d . B . N2 N 0.35080(16) 0.4805(2) 0.51195(8) 0.0205(4) Uani 1 1 d . B . C1 C 0.0420(2) 0.1700(2) 0.42801(9) 0.0209(5) Uani 1 1 d . B 2 C2 C -0.0349(2) 0.1032(3) 0.38719(10) 0.0257(5) Uani 1 1 d . B 2 H2 H -0.0088 0.0905 0.3521 0.031 Uiso 1 1 calc R B 2 C3 C -0.1471(2) 0.0560(3) 0.39707(10) 0.0278(5) Uani 1 1 d . B 2 H3 H -0.1987 0.0152 0.3682 0.033 Uiso 1 1 calc R B 2 C4 C -0.1871(2) 0.0666(3) 0.44880(10) 0.0263(5) Uani 1 1 d . B 2 H4 H -0.2644 0.0321 0.4554 0.032 Uiso 1 1 calc R B 2 C5 C -0.1124(2) 0.1278(3) 0.48963(10) 0.0231(5) Uani 1 1 d . B 2 H5 H -0.1380 0.1333 0.5251 0.028 Uiso 1 1 calc R B 2 C6 C 0.0018(2) 0.1830(2) 0.48056(9) 0.0201(4) Uani 1 1 d . B 2 C7 C 0.0652(2) 0.2551(2) 0.52590(9) 0.0198(4) Uani 1 1 d . B 2 H7 H 0.0277 0.2560 0.5587 0.024 Uiso 1 1 calc R B 2 C8 C 0.2186(2) 0.3983(2) 0.57745(9) 0.0210(5) Uani 1 1 d . B 2 C9 C 0.3508(2) 0.4329(3) 0.56885(9) 0.0225(5) Uani 1 1 d . B 2 H9A H 0.3825 0.5082 0.5942 0.027 Uiso 1 1 calc R B 2 H9B H 0.4022 0.3480 0.5754 0.027 Uiso 1 1 calc R B 2 C10 C 0.3669(2) 0.6131(3) 0.50200(10) 0.0227(5) Uani 1 1 d . B 2 H10 H 0.4079 0.6692 0.5299 0.027 Uiso 1 1 calc R B 2 C11 C 0.3265(2) 0.6807(2) 0.45134(10) 0.0229(5) Uani 1 1 d . B 2 C12 C 0.3638(2) 0.8188(3) 0.44073(11) 0.0274(5) Uani 1 1 d . B 2 H12 H 0.4268 0.8609 0.4641 0.033 Uiso 1 1 calc R B 2 C13 C 0.3108(2) 0.8941(3) 0.39707(11) 0.0323(6) Uani 1 1 d . B 2 H13 H 0.3379 0.9867 0.3898 0.039 Uiso 1 1 calc R B 2 C14 C 0.2167(3) 0.8328(3) 0.36355(11) 0.0335(6) Uani 1 1 d . B 2 H14 H 0.1802 0.8843 0.3332 0.040 Uiso 1 1 calc R B 2 C15 C 0.1755(2) 0.6991(3) 0.37348(10) 0.0280(5) Uani 1 1 d . B 2 H15 H 0.1101 0.6604 0.3505 0.034 Uiso 1 1 calc R B 2 C16 C 0.2296(2) 0.6195(3) 0.41744(9) 0.0223(5) Uani 1 1 d . B 2 C17 C 0.2182(3) 0.3082(3) 0.62876(10) 0.0312(6) Uani 1 1 d . B 2 H17A H 0.2668 0.2231 0.6251 0.047 Uiso 1 1 calc R B 2 H17B H 0.1352 0.2812 0.6337 0.047 Uiso 1 1 calc R B 2 H17C H 0.2525 0.3627 0.6603 0.047 Uiso 1 1 calc R B 2 C18 C 0.1442(2) 0.5324(3) 0.58095(11) 0.0298(5) Uani 1 1 d . B 2 H18A H 0.1464 0.5874 0.5475 0.045 Uiso 1 1 calc R B 2 H18B H 0.1778 0.5889 0.6121 0.045 Uiso 1 1 calc R B 2 H18C H 0.0605 0.5073 0.5855 0.045 Uiso 1 1 calc R B 2 C19 C 0.5349(3) 0.2132(3) 0.27482(13) 0.0394(7) Uani 1 1 d . C 2 H19 H 0.4662 0.2755 0.2826 0.047 Uiso 1 1 calc R C 2 Cl5' Cl 0.1431(14) 0.1540(4) 0.2663(3) 0.077(3) Uani 0.401(13) 1 d P A 2 Cl6' Cl -0.0099(4) 0.3892(11) 0.28549(19) 0.0640(14) Uani 0.401(13) 1 d P A 2 Cl7' Cl 0.2299(12) 0.4352(17) 0.2515(6) 0.0479(17) Uani 0.401(13) 1 d P A 2 C20 C 0.1399(3) 0.3251(3) 0.28882(11) 0.0347(6) Uani 0.599(13) 1 d P A 1 H20 H 0.1546 0.3457 0.3286 0.042 Uiso 0.599(13) 1 calc PR A 1 C20' C 0.1399(3) 0.3251(3) 0.28882(11) 0.0347(6) Uani 0.401(13) 1 d P A 2 H20' H 0.1746 0.3268 0.3278 0.042 Uiso 0.401(13) 1 calc PR A 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 0.01497(5) 0.02212(5) 0.01857(5) -0.00113(3) 0.00087(3) -0.00064(3) Cl1 0.0216(3) 0.0416(4) 0.0240(3) -0.0050(2) 0.0061(2) -0.0043(2) Cl2 0.0444(5) 0.0637(6) 0.0684(6) -0.0155(4) -0.0113(4) -0.0114(4) Cl3 0.0593(5) 0.0557(5) 0.0677(6) 0.0081(4) 0.0279(4) 0.0068(4) Cl4 0.0497(5) 0.0708(6) 0.0432(4) -0.0097(4) -0.0065(4) -0.0007(4) Cl5 0.0537(15) 0.0466(9) 0.0349(8) -0.0028(6) 0.0034(9) -0.0045(9) Cl6 0.0352(8) 0.082(3) 0.077(2) 0.0362(19) -0.0135(9) -0.0053(11) Cl7 0.065(4) 0.054(3) 0.0467(12) 0.0099(16) 0.010(2) -0.023(2) O1 0.0222(8) 0.0281(9) 0.0194(8) -0.0034(6) 0.0026(6) -0.0053(7) O2 0.0160(8) 0.0248(8) 0.0239(8) 0.0012(6) -0.0003(6) -0.0001(6) O3 0.0200(9) 0.0280(9) 0.0321(9) -0.0010(7) 0.0000(7) 0.0044(7) N1 0.0177(9) 0.0201(9) 0.0162(9) -0.0013(7) -0.0007(7) 0.0025(7) N2 0.0135(9) 0.0257(10) 0.0217(9) 0.0013(8) -0.0013(7) -0.0003(8) C1 0.0197(11) 0.0183(11) 0.0240(11) 0.0025(8) -0.0006(9) 0.0017(9) C2 0.0271(13) 0.0253(12) 0.0239(11) -0.0009(9) -0.0018(10) -0.0031(10) C3 0.0290(13) 0.0229(12) 0.0295(12) 0.0005(10) -0.0070(10) -0.0071(10) C4 0.0199(12) 0.0229(12) 0.0352(13) 0.0018(10) -0.0009(10) -0.0038(9) C5 0.0197(11) 0.0218(11) 0.0279(12) 0.0015(9) 0.0028(9) 0.0018(9) C6 0.0181(11) 0.0173(10) 0.0242(11) 0.0014(8) -0.0011(9) 0.0016(8) C7 0.0199(11) 0.0203(11) 0.0192(10) 0.0016(8) 0.0025(9) 0.0021(9) C8 0.0208(11) 0.0227(11) 0.0189(10) -0.0014(9) -0.0009(9) -0.0010(9) C9 0.0202(11) 0.0264(12) 0.0202(11) -0.0004(9) -0.0018(9) -0.0016(9) C10 0.0135(10) 0.0267(12) 0.0278(12) -0.0025(9) 0.0010(9) -0.0024(9) C11 0.0173(11) 0.0243(12) 0.0280(12) 0.0011(9) 0.0065(9) 0.0014(9) C12 0.0221(12) 0.0264(13) 0.0352(13) -0.0012(10) 0.0097(10) -0.0024(10) C13 0.0345(14) 0.0253(13) 0.0396(15) 0.0049(11) 0.0164(12) -0.0024(11) C14 0.0414(16) 0.0327(14) 0.0271(13) 0.0074(10) 0.0076(12) 0.0057(12) C15 0.0280(13) 0.0304(13) 0.0252(12) 0.0029(10) 0.0012(10) 0.0035(10) C16 0.0193(11) 0.0250(12) 0.0233(11) 0.0003(9) 0.0062(9) 0.0012(9) C17 0.0335(14) 0.0393(15) 0.0192(11) 0.0047(10) -0.0046(10) -0.0075(11) C18 0.0245(13) 0.0266(13) 0.0380(14) -0.0084(11) 0.0026(11) 0.0014(10) C19 0.0285(14) 0.0439(17) 0.0454(17) -0.0072(13) 0.0028(12) 0.0005(12) Cl5' 0.145(8) 0.0410(14) 0.054(2) 0.0000(13) 0.050(4) -0.002(2) Cl6' 0.0362(14) 0.086(4) 0.0677(18) 0.002(2) -0.0032(12) 0.0077(18) Cl7' 0.050(4) 0.056(5) 0.0380(18) 0.012(2) 0.005(2) -0.019(3) C20 0.0342(15) 0.0439(16) 0.0258(13) 0.0075(11) 0.0014(11) -0.0046(12) C20' 0.0342(15) 0.0439(16) 0.0258(13) 0.0075(11) 0.0014(11) -0.0046(12) _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 O3 1.6931(17) . ? Re1 O1 1.9999(16) . ? Re1 O2 2.0094(16) . ? Re1 N1 2.0618(19) . ? Re1 N2 2.0727(19) . ? Re1 Cl1 2.4401(6) . ? Cl2 C19 1.755(3) . ? Cl3 C19 1.753(3) . ? Cl4 C19 1.761(3) . ? Cl5 C20 1.782(4) . ? Cl6 C20 1.754(4) . ? Cl7 C20 1.742(12) . ? O1 C1 1.332(3) . ? O2 C16 1.337(3) . ? N1 C7 1.288(3) . ? N1 C8 1.520(3) . ? N2 C10 1.296(3) . ? N2 C9 1.477(3) . ? C1 C2 1.405(3) . ? C1 C6 1.423(3) . ? C2 C3 1.373(4) . ? C2 H2 0.9500 . ? C3 C4 1.400(4) . ? C3 H3 0.9500 . ? C4 C5 1.369(3) . ? C4 H4 0.9500 . ? C5 C6 1.415(3) . ? C5 H5 0.9500 . ? C6 C7 1.434(3) . ? C7 H7 0.9500 . ? C8 C18 1.524(3) . ? C8 C17 1.528(3) . ? C8 C9 1.545(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.436(3) . ? C10 H10 0.9500 . ? C11 C12 1.406(3) . ? C11 C16 1.420(3) . ? C12 C13 1.375(4) . ? C12 H12 0.9500 . ? C13 C14 1.394(4) . ? C13 H13 0.9500 . ? C14 C15 1.377(4) . ? C14 H14 0.9500 . ? C15 C16 1.406(3) . ? C15 H15 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19 1.0000 . ? C20 H20 1.0000 . ? 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 O3 Re1 O1 103.50(8) . . ? O3 Re1 O2 169.97(8) . . ? O1 Re1 O2 82.57(7) . . ? O3 Re1 N1 94.01(8) . . ? O1 Re1 N1 92.76(7) . . ? O2 Re1 N1 93.65(7) . . ? O3 Re1 N2 94.74(8) . . ? O1 Re1 N2 160.21(7) . . ? O2 Re1 N2 80.51(7) . . ? N1 Re1 N2 78.20(7) . . ? O3 Re1 Cl1 89.64(6) . . ? O1 Re1 Cl1 89.00(5) . . ? O2 Re1 Cl1 82.43(5) . . ? N1 Re1 Cl1 175.46(5) . . ? N2 Re1 Cl1 98.83(6) . . ? C1 O1 Re1 125.46(14) . . ? C16 O2 Re1 128.67(14) . . ? C7 N1 C8 120.08(19) . . ? C7 N1 Re1 123.99(15) . . ? C8 N1 Re1 115.92(14) . . ? C10 N2 C9 119.3(2) . . ? C10 N2 Re1 129.94(16) . . ? C9 N2 Re1 107.74(14) . . ? O1 C1 C2 116.6(2) . . ? O1 C1 C6 125.4(2) . . ? C2 C1 C6 117.9(2) . . ? C3 C2 C1 121.2(2) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C2 C3 C4 121.3(2) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C5 C4 C3 118.5(2) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C4 C5 C6 121.9(2) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C5 C6 C1 119.1(2) . . ? C5 C6 C7 115.5(2) . . ? C1 C6 C7 125.3(2) . . ? N1 C7 C6 126.9(2) . . ? N1 C7 H7 116.6 . . ? C6 C7 H7 116.6 . . ? N1 C8 C18 107.53(18) . . ? N1 C8 C17 111.95(19) . . ? C18 C8 C17 111.7(2) . . ? N1 C8 C9 105.81(17) . . ? C18 C8 C9 111.3(2) . . ? C17 C8 C9 108.44(19) . . ? N2 C9 C8 106.80(18) . . ? N2 C9 H9A 110.4 . . ? C8 C9 H9A 110.4 . . ? N2 C9 H9B 110.4 . . ? C8 C9 H9B 110.4 . . ? H9A C9 H9B 108.6 . . ? N2 C10 C11 124.0(2) . . ? N2 C10 H10 118.0 . . ? C11 C10 H10 118.0 . . ? C12 C11 C16 119.4(2) . . ? C12 C11 C10 120.3(2) . . ? C16 C11 C10 118.9(2) . . ? C13 C12 C11 121.2(3) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C14 119.1(2) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C15 C14 C13 121.4(3) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C14 C15 C16 120.4(3) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? O2 C16 C15 119.4(2) . . ? O2 C16 C11 122.0(2) . . ? C15 C16 C11 118.5(2) . . ? C8 C17 H17A 109.5 . . ? C8 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C8 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C8 C18 H18A 109.5 . . ? C8 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C8 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? Cl3 C19 Cl2 110.25(17) . . ? Cl3 C19 Cl4 110.10(17) . . ? Cl2 C19 Cl4 109.44(17) . . ? Cl3 C19 H19 109.0 . . ? Cl2 C19 H19 109.0 . . ? Cl4 C19 H19 109.0 . . ? Cl7 C20 Cl6 109.0(3) . . ? Cl7 C20 Cl5 111.1(3) . . ? Cl6 C20 Cl5 109.0(2) . . ? Cl7 C20 H20 109.3 . . ? Cl6 C20 H20 109.3 . . ? Cl5 C20 H20 109.3 . . ? 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 O3 Re1 O1 C1 92.79(18) . . . . ? O2 Re1 O1 C1 -95.33(18) . . . . ? N1 Re1 O1 C1 -2.01(18) . . . . ? N2 Re1 O1 C1 -63.9(3) . . . . ? Cl1 Re1 O1 C1 -177.83(18) . . . . ? O3 Re1 O2 C16 -20.3(5) . . . . ? O1 Re1 O2 C16 -148.29(19) . . . . ? N1 Re1 O2 C16 119.39(18) . . . . ? N2 Re1 O2 C16 42.01(18) . . . . ? Cl1 Re1 O2 C16 -58.31(18) . . . . ? O3 Re1 N1 C7 -100.22(19) . . . . ? O1 Re1 N1 C7 3.53(19) . . . . ? O2 Re1 N1 C7 86.26(18) . . . . ? N2 Re1 N1 C7 165.77(19) . . . . ? Cl1 Re1 N1 C7 116.4(6) . . . . ? O3 Re1 N1 C8 80.73(15) . . . . ? O1 Re1 N1 C8 -175.51(15) . . . . ? O2 Re1 N1 C8 -92.79(15) . . . . ? N2 Re1 N1 C8 -13.28(14) . . . . ? Cl1 Re1 N1 C8 -62.7(7) . . . . ? O3 Re1 N2 C10 144.8(2) . . . . ? O1 Re1 N2 C10 -57.9(3) . . . . ? O2 Re1 N2 C10 -26.3(2) . . . . ? N1 Re1 N2 C10 -122.1(2) . . . . ? Cl1 Re1 N2 C10 54.4(2) . . . . ? O3 Re1 N2 C9 -55.38(15) . . . . ? O1 Re1 N2 C9 101.9(2) . . . . ? O2 Re1 N2 C9 133.52(15) . . . . ? N1 Re1 N2 C9 37.73(14) . . . . ? Cl1 Re1 N2 C9 -145.75(13) . . . . ? Re1 O1 C1 C2 178.03(16) . . . . ? Re1 O1 C1 C6 -0.2(3) . . . . ? O1 C1 C2 C3 -176.3(2) . . . . ? C6 C1 C2 C3 2.1(4) . . . . ? C1 C2 C3 C4 -2.9(4) . . . . ? C2 C3 C4 C5 1.1(4) . . . . ? C3 C4 C5 C6 1.6(4) . . . . ? C4 C5 C6 C1 -2.4(3) . . . . ? C4 C5 C6 C7 174.6(2) . . . . ? O1 C1 C6 C5 178.8(2) . . . . ? C2 C1 C6 C5 0.5(3) . . . . ? O1 C1 C6 C7 2.1(4) . . . . ? C2 C1 C6 C7 -176.1(2) . . . . ? C8 N1 C7 C6 176.0(2) . . . . ? Re1 N1 C7 C6 -3.0(3) . . . . ? C5 C6 C7 N1 -177.0(2) . . . . ? C1 C6 C7 N1 -0.3(4) . . . . ? C7 N1 C8 C18 -72.6(3) . . . . ? Re1 N1 C8 C18 106.46(18) . . . . ? C7 N1 C8 C17 50.4(3) . . . . ? Re1 N1 C8 C17 -130.48(18) . . . . ? C7 N1 C8 C9 168.4(2) . . . . ? Re1 N1 C8 C9 -12.5(2) . . . . ? C10 N2 C9 C8 106.9(2) . . . . ? Re1 N2 C9 C8 -55.45(19) . . . . ? N1 C8 C9 N2 42.9(2) . . . . ? C18 C8 C9 N2 -73.6(2) . . . . ? C17 C8 C9 N2 163.15(19) . . . . ? C9 N2 C10 C11 -156.2(2) . . . . ? Re1 N2 C10 C11 1.6(3) . . . . ? N2 C10 C11 C12 -169.9(2) . . . . ? N2 C10 C11 C16 23.4(3) . . . . ? C16 C11 C12 C13 -2.1(4) . . . . ? C10 C11 C12 C13 -168.8(2) . . . . ? C11 C12 C13 C14 1.3(4) . . . . ? C12 C13 C14 C15 0.4(4) . . . . ? C13 C14 C15 C16 -1.4(4) . . . . ? Re1 O2 C16 C15 150.79(18) . . . . ? Re1 O2 C16 C11 -33.2(3) . . . . ? C14 C15 C16 O2 176.7(2) . . . . ? C14 C15 C16 C11 0.6(4) . . . . ? C12 C11 C16 O2 -174.9(2) . . . . ? C10 C11 C16 O2 -8.0(3) . . . . ? C12 C11 C16 C15 1.1(3) . . . . ? C10 C11 C16 C15 168.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.021 _refine_diff_density_min -0.658 _refine_diff_density_rms 0.075 _database_code_depnum_ccdc_archive 'CCDC 933550' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_DAR45b _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C36 H18 N4 O7 Re2, 4(C H Cl3)' _chemical_formula_sum 'C40 H40 Cl12 N4 O7 Re2' _chemical_melting_point ? _exptl_crystal_description Prism _exptl_crystal_colour Green _diffrn_ambient_temperature 173(2) _chemical_formula_weight 1486.56 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' N N 0.0061 0.0033 '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' Cl Cl 0.1484 0.1585 '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_int_tables_number 14 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 9.6016(16) _cell_length_b 17.819(3) _cell_length_c 14.807(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.941(2) _cell_angle_gamma 90.00 _cell_volume 2533.1(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9914 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 27.5 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.949 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1436 _exptl_absorpt_coefficient_mu 5.458 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.30 _exptl_absorpt_correction_T_max 0.41 _exptl_absorpt_process_details ; Data were corrected for decay and absorption using the program SADABS (Sheldrick, G. M. (2003). SADABS. Version 2.10. University of G\"ottingen, Germany). ; _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 28698 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 27.58 _reflns_number_total 5828 _reflns_number_gt 5043 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2008)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2008)' _computing_data_reduction 'APEX2 (Bruker AXS, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-SEED, Barbour, 2001' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.0313P)^2^+16.1509P] 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 5828 _refine_ls_number_parameters 297 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0900 _refine_ls_wR_factor_gt 0.0862 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 0.16189(2) 0.032690(11) 0.436058(13) 0.02341(7) Uani 1 1 d . . . Cl1 Cl -0.4117(2) 0.18609(12) -0.03877(13) 0.0606(5) Uani 1 1 d . . . Cl2 Cl -0.3452(2) 0.22041(15) -0.22264(12) 0.0677(6) Uani 1 1 d . . . Cl3 Cl -0.1330(2) 0.23101(13) -0.08297(16) 0.0657(5) Uani 1 1 d . . . Cl4 Cl 0.2428(2) 0.14037(13) 0.08302(16) 0.0682(6) Uani 1 1 d . . . Cl5 Cl 0.3683(3) 0.00012(14) 0.1353(2) 0.0811(7) Uani 1 1 d . . . Cl6 Cl 0.4906(3) 0.14094(14) 0.19577(15) 0.0720(6) Uani 1 1 d . . . O1 O 0.1687(4) 0.1220(2) 0.5212(2) 0.0276(8) Uani 1 1 d . . . O2 O 0.0371(4) 0.0934(2) 0.3515(2) 0.0309(8) Uani 1 1 d . . . O3 O 0.0000 0.0000 0.5000 0.0239(10) Uani 1 2 d S . . O4 O 0.3140(4) 0.0522(2) 0.3817(3) 0.0346(9) Uani 1 1 d . . . N1 N 0.2612(5) -0.0400(3) 0.5248(3) 0.0262(9) Uani 1 1 d . . . N2 N 0.1295(5) -0.0653(3) 0.3655(3) 0.0267(9) Uani 1 1 d . . . C1 C 0.2173(6) 0.1171(3) 0.6060(4) 0.0284(11) Uani 1 1 d . . . C2 C 0.2051(7) 0.1825(3) 0.6588(4) 0.0370(13) Uani 1 1 d . . . H15 H 0.1649 0.2263 0.6328 0.044 Uiso 1 1 calc R . . C3 C 0.2505(8) 0.1839(4) 0.7472(4) 0.0453(16) Uani 1 1 d . . . H14 H 0.2411 0.2289 0.7810 0.054 Uiso 1 1 calc R . . C4 C 0.3091(8) 0.1221(4) 0.7880(4) 0.0475(17) Uani 1 1 d . . . H13 H 0.3401 0.1243 0.8492 0.057 Uiso 1 1 calc R . . C5 C 0.3222(7) 0.0566(4) 0.7385(4) 0.0391(14) Uani 1 1 d . . . H12 H 0.3628 0.0137 0.7663 0.047 Uiso 1 1 calc R . . C6 C 0.2765(6) 0.0524(3) 0.6475(4) 0.0310(12) Uani 1 1 d . . . C7 C 0.2958(6) -0.0209(3) 0.6058(4) 0.0303(12) Uani 1 1 d . . . H10 H 0.3384 -0.0585 0.6423 0.036 Uiso 1 1 calc R . . C8 C 0.2836(6) -0.1177(3) 0.4880(4) 0.0295(11) Uani 1 1 d . . . C9 C 0.1625(6) -0.1329(3) 0.4199(4) 0.0283(11) Uani 1 1 d . . . H8A H 0.1886 -0.1745 0.3792 0.034 Uiso 1 1 calc R . . H8B H 0.0787 -0.1485 0.4532 0.034 Uiso 1 1 calc R . . C10 C 0.0760(6) -0.0677(3) 0.2851(4) 0.0301(11) Uani 1 1 d . . . H7 H 0.0747 -0.1152 0.2559 0.036 Uiso 1 1 calc R . . C11 C 0.0176(6) -0.0051(3) 0.2350(4) 0.0311(12) Uani 1 1 d . . . C12 C -0.0329(7) -0.0206(4) 0.1467(4) 0.0393(14) Uani 1 1 d . . . H5 H -0.0168 -0.0691 0.1225 0.047 Uiso 1 1 calc R . . C13 C -0.1026(7) 0.0295(4) 0.0950(4) 0.0454(16) Uani 1 1 d . . . H4 H -0.1345 0.0169 0.0359 0.054 Uiso 1 1 calc R . . C14 C -0.1263(7) 0.1000(4) 0.1308(4) 0.0458(16) Uani 1 1 d . . . H3 H -0.1764 0.1359 0.0958 0.055 Uiso 1 1 calc R . . C15 C -0.0794(7) 0.1194(4) 0.2154(4) 0.0389(14) Uani 1 1 d . . . H2 H -0.0975 0.1684 0.2376 0.047 Uiso 1 1 calc R . . C16 C -0.0044(6) 0.0679(3) 0.2707(4) 0.0299(11) Uani 1 1 d . . . C17 C 0.2790(7) -0.1775(3) 0.5615(4) 0.0369(13) Uani 1 1 d . . . H17A H 0.3618 -0.1731 0.6007 0.055 Uiso 1 1 calc R . . H17B H 0.2769 -0.2274 0.5336 0.055 Uiso 1 1 calc R . . H17C H 0.1952 -0.1706 0.5975 0.055 Uiso 1 1 calc R . . C18 C 0.4244(6) -0.1179(4) 0.4407(4) 0.0397(14) Uani 1 1 d . . . H18A H 0.4208 -0.0833 0.3893 0.060 Uiso 1 1 calc R . . H18B H 0.4450 -0.1687 0.4193 0.060 Uiso 1 1 calc R . . H18C H 0.4976 -0.1018 0.4834 0.060 Uiso 1 1 calc R . . C19 C -0.3090(7) 0.2427(4) -0.1089(4) 0.0411(14) Uani 1 1 d . . . H19 H -0.3343 0.2964 -0.0986 0.049 Uiso 1 1 calc R . . C20 C 0.3374(8) 0.0925(4) 0.1677(5) 0.0482(16) Uani 1 1 d . . . H20 H 0.2786 0.0911 0.2228 0.058 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 0.02879(12) 0.02118(11) 0.02030(11) 0.00127(8) 0.00196(7) -0.00187(8) Cl1 0.0651(12) 0.0688(12) 0.0479(10) 0.0052(9) -0.0023(9) -0.0246(10) Cl2 0.0696(13) 0.1008(17) 0.0328(9) -0.0073(10) 0.0014(8) 0.0192(12) Cl3 0.0524(11) 0.0727(14) 0.0716(13) -0.0047(11) -0.0052(10) -0.0088(10) Cl4 0.0653(13) 0.0648(13) 0.0743(14) 0.0168(11) -0.0092(11) 0.0024(10) Cl5 0.0659(14) 0.0608(13) 0.116(2) -0.0141(14) -0.0225(14) 0.0104(11) Cl6 0.0722(14) 0.0798(15) 0.0638(12) 0.0142(11) -0.0083(10) -0.0330(12) O1 0.039(2) 0.0212(17) 0.0222(18) -0.0013(14) -0.0009(15) -0.0042(16) O2 0.041(2) 0.0261(19) 0.0257(19) 0.0020(15) -0.0018(16) 0.0001(17) O3 0.027(3) 0.021(2) 0.023(2) 0.001(2) 0.004(2) -0.002(2) O4 0.037(2) 0.040(2) 0.027(2) 0.0046(17) 0.0055(17) -0.0088(18) N1 0.025(2) 0.031(2) 0.022(2) 0.0000(18) 0.0037(17) 0.0024(18) N2 0.029(2) 0.026(2) 0.025(2) 0.0010(18) 0.0019(18) 0.0008(18) C1 0.031(3) 0.030(3) 0.025(3) 0.000(2) 0.003(2) -0.008(2) C2 0.049(4) 0.025(3) 0.037(3) -0.005(2) 0.004(3) -0.010(3) C3 0.056(4) 0.043(4) 0.038(3) -0.013(3) 0.007(3) -0.018(3) C4 0.053(4) 0.063(5) 0.027(3) -0.008(3) -0.003(3) -0.019(3) C5 0.039(3) 0.047(4) 0.032(3) 0.000(3) -0.007(2) -0.010(3) C6 0.028(3) 0.040(3) 0.025(3) 0.000(2) 0.001(2) -0.007(2) C7 0.027(3) 0.036(3) 0.028(3) 0.001(2) 0.000(2) -0.001(2) C8 0.029(3) 0.029(3) 0.030(3) 0.002(2) 0.002(2) 0.003(2) C9 0.034(3) 0.026(3) 0.026(3) 0.000(2) 0.002(2) 0.003(2) C10 0.031(3) 0.034(3) 0.026(3) -0.004(2) 0.004(2) 0.001(2) C11 0.028(3) 0.039(3) 0.026(3) 0.002(2) 0.003(2) -0.001(2) C12 0.033(3) 0.054(4) 0.031(3) -0.007(3) 0.003(2) -0.006(3) C13 0.045(4) 0.066(5) 0.025(3) -0.004(3) -0.002(3) 0.000(3) C14 0.043(4) 0.063(4) 0.032(3) 0.012(3) -0.004(3) 0.007(3) C15 0.040(3) 0.044(3) 0.033(3) 0.010(3) 0.002(3) 0.007(3) C16 0.027(3) 0.035(3) 0.028(3) 0.002(2) 0.004(2) -0.003(2) C17 0.048(4) 0.029(3) 0.034(3) 0.004(2) 0.000(3) 0.009(3) C18 0.031(3) 0.052(4) 0.036(3) 0.001(3) 0.003(2) 0.008(3) C19 0.052(4) 0.033(3) 0.038(3) -0.005(3) 0.007(3) 0.002(3) C20 0.051(4) 0.045(4) 0.049(4) 0.007(3) 0.002(3) -0.008(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 O4 1.714(4) . ? Re1 O3 1.9236(3) . ? Re1 O1 2.030(4) . ? Re1 O2 2.031(4) . ? Re1 N2 2.057(5) . ? Re1 N1 2.067(4) . ? Cl1 C19 1.761(7) . ? Cl2 C19 1.759(7) . ? Cl3 C19 1.739(7) . ? Cl4 C20 1.757(7) . ? Cl5 C20 1.741(8) . ? Cl6 C20 1.750(7) . ? O1 C1 1.336(6) . ? O2 C16 1.335(7) . ? O3 Re1 1.9236(3) 3_556 ? N1 C7 1.285(7) . ? N1 C8 1.505(7) . ? N2 C10 1.290(7) . ? N2 C9 1.480(7) . ? C1 C2 1.409(8) . ? C1 C6 1.421(8) . ? C2 C3 1.372(9) . ? C2 H15 0.9500 . ? C3 C4 1.372(11) . ? C3 H14 0.9500 . ? C4 C5 1.385(10) . ? C4 H13 0.9500 . ? C5 C6 1.412(8) . ? C5 H12 0.9500 . ? C6 C7 1.457(8) . ? C7 H10 0.9500 . ? C8 C17 1.525(8) . ? C8 C18 1.532(8) . ? C8 C9 1.551(8) . ? C9 H8A 0.9900 . ? C9 H8B 0.9900 . ? C10 C11 1.448(8) . ? C10 H7 0.9500 . ? C11 C12 1.414(8) . ? C11 C16 1.422(8) . ? C12 C13 1.347(10) . ? C12 H5 0.9500 . ? C13 C14 1.384(10) . ? C13 H4 0.9500 . ? C14 C15 1.368(9) . ? C14 H3 0.9500 . ? C15 C16 1.416(8) . ? C15 H2 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19 1.0000 . ? C20 H20 1.0000 . ? 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 O4 Re1 O3 173.58(15) . . ? O4 Re1 O1 96.52(18) . . ? O3 Re1 O1 87.13(11) . . ? O4 Re1 O2 95.82(18) . . ? O3 Re1 O2 89.51(11) . . ? O1 Re1 O2 88.72(15) . . ? O4 Re1 N2 93.22(19) . . ? O3 Re1 N2 82.90(13) . . ? O1 Re1 N2 169.81(16) . . ? O2 Re1 N2 93.26(16) . . ? O4 Re1 N1 92.13(19) . . ? O3 Re1 N1 82.27(12) . . ? O1 Re1 N1 94.98(16) . . ? O2 Re1 N1 170.80(17) . . ? N2 Re1 N1 81.65(18) . . ? C1 O1 Re1 122.7(3) . . ? C16 O2 Re1 122.4(4) . . ? Re1 O3 Re1 179.999(11) . 3_556 ? C7 N1 C8 123.1(5) . . ? C7 N1 Re1 122.4(4) . . ? C8 N1 Re1 114.4(3) . . ? C10 N2 C9 123.6(5) . . ? C10 N2 Re1 123.5(4) . . ? C9 N2 Re1 112.7(3) . . ? O1 C1 C2 115.9(5) . . ? O1 C1 C6 126.2(5) . . ? C2 C1 C6 117.9(5) . . ? C3 C2 C1 121.1(6) . . ? C3 C2 H15 119.5 . . ? C1 C2 H15 119.5 . . ? C2 C3 C4 121.8(6) . . ? C2 C3 H14 119.1 . . ? C4 C3 H14 119.1 . . ? C3 C4 C5 118.8(6) . . ? C3 C4 H13 120.6 . . ? C5 C4 H13 120.6 . . ? C4 C5 C6 121.4(6) . . ? C4 C5 H12 119.3 . . ? C6 C5 H12 119.3 . . ? C5 C6 C1 119.0(6) . . ? C5 C6 C7 114.4(6) . . ? C1 C6 C7 126.6(5) . . ? N1 C7 C6 126.9(5) . . ? N1 C7 H10 116.5 . . ? C6 C7 H10 116.5 . . ? N1 C8 C17 112.3(5) . . ? N1 C8 C18 107.4(5) . . ? C17 C8 C18 111.2(5) . . ? N1 C8 C9 106.6(4) . . ? C17 C8 C9 108.2(5) . . ? C18 C8 C9 111.1(5) . . ? N2 C9 C8 111.3(4) . . ? N2 C9 H8A 109.4 . . ? C8 C9 H8A 109.4 . . ? N2 C9 H8B 109.4 . . ? C8 C9 H8B 109.4 . . ? H8A C9 H8B 108.0 . . ? N2 C10 C11 126.4(5) . . ? N2 C10 H7 116.8 . . ? C11 C10 H7 116.8 . . ? C12 C11 C16 118.1(6) . . ? C12 C11 C10 116.6(6) . . ? C16 C11 C10 125.0(5) . . ? C13 C12 C11 123.8(6) . . ? C13 C12 H5 118.1 . . ? C11 C12 H5 118.1 . . ? C12 C13 C14 117.8(6) . . ? C12 C13 H4 121.1 . . ? C14 C13 H4 121.1 . . ? C15 C14 C13 121.7(6) . . ? C15 C14 H3 119.1 . . ? C13 C14 H3 119.1 . . ? C14 C15 C16 121.5(6) . . ? C14 C15 H2 119.3 . . ? C16 C15 H2 119.3 . . ? O2 C16 C15 116.0(5) . . ? O2 C16 C11 126.9(5) . . ? C15 C16 C11 117.0(5) . . ? C8 C17 H17A 109.5 . . ? C8 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C8 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C8 C18 H18A 109.5 . . ? C8 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C8 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? Cl3 C19 Cl2 111.1(4) . . ? Cl3 C19 Cl1 110.6(4) . . ? Cl2 C19 Cl1 109.4(4) . . ? Cl3 C19 H19 108.6 . . ? Cl2 C19 H19 108.6 . . ? Cl1 C19 H19 108.6 . . ? Cl5 C20 Cl6 112.6(4) . . ? Cl5 C20 Cl4 110.6(4) . . ? Cl6 C20 Cl4 110.6(4) . . ? Cl5 C20 H20 107.6 . . ? Cl6 C20 H20 107.6 . . ? Cl4 C20 H20 107.6 . . ? 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 O4 Re1 O1 C1 -97.3(4) . . . . ? O3 Re1 O1 C1 77.4(4) . . . . ? O2 Re1 O1 C1 167.0(4) . . . . ? N2 Re1 O1 C1 65.6(11) . . . . ? N1 Re1 O1 C1 -4.5(4) . . . . ? O4 Re1 O2 C16 78.9(4) . . . . ? O3 Re1 O2 C16 -97.5(4) . . . . ? O1 Re1 O2 C16 175.3(4) . . . . ? N2 Re1 O2 C16 -14.7(4) . . . . ? N1 Re1 O2 C16 -70.8(11) . . . . ? O4 Re1 O3 Re1 63(3) . . . 3_556 ? O1 Re1 O3 Re1 -62(3) . . . 3_556 ? O2 Re1 O3 Re1 -151(3) . . . 3_556 ? N2 Re1 O3 Re1 116(3) . . . 3_556 ? N1 Re1 O3 Re1 33(3) . . . 3_556 ? O4 Re1 N1 C7 100.6(5) . . . . ? O3 Re1 N1 C7 -82.5(4) . . . . ? O1 Re1 N1 C7 3.9(4) . . . . ? O2 Re1 N1 C7 -109.5(10) . . . . ? N2 Re1 N1 C7 -166.4(5) . . . . ? O4 Re1 N1 C8 -82.0(4) . . . . ? O3 Re1 N1 C8 94.9(3) . . . . ? O1 Re1 N1 C8 -178.7(3) . . . . ? O2 Re1 N1 C8 67.9(11) . . . . ? N2 Re1 N1 C8 11.0(3) . . . . ? O4 Re1 N2 C10 -81.2(5) . . . . ? O3 Re1 N2 C10 103.9(4) . . . . ? O1 Re1 N2 C10 115.8(9) . . . . ? O2 Re1 N2 C10 14.8(5) . . . . ? N1 Re1 N2 C10 -172.9(5) . . . . ? O4 Re1 N2 C9 104.0(4) . . . . ? O3 Re1 N2 C9 -70.9(3) . . . . ? O1 Re1 N2 C9 -59.0(11) . . . . ? O2 Re1 N2 C9 -160.0(4) . . . . ? N1 Re1 N2 C9 12.3(4) . . . . ? Re1 O1 C1 C2 -175.2(4) . . . . ? Re1 O1 C1 C6 3.4(7) . . . . ? O1 C1 C2 C3 179.5(6) . . . . ? C6 C1 C2 C3 0.8(9) . . . . ? C1 C2 C3 C4 -0.1(10) . . . . ? C2 C3 C4 C5 -0.2(10) . . . . ? C3 C4 C5 C6 -0.1(10) . . . . ? C4 C5 C6 C1 0.7(9) . . . . ? C4 C5 C6 C7 -179.0(6) . . . . ? O1 C1 C6 C5 -179.6(5) . . . . ? C2 C1 C6 C5 -1.0(8) . . . . ? O1 C1 C6 C7 0.1(9) . . . . ? C2 C1 C6 C7 178.7(5) . . . . ? C8 N1 C7 C6 -179.1(5) . . . . ? Re1 N1 C7 C6 -1.9(8) . . . . ? C5 C6 C7 N1 178.8(6) . . . . ? C1 C6 C7 N1 -1.0(9) . . . . ? C7 N1 C8 C17 29.1(7) . . . . ? Re1 N1 C8 C17 -148.3(4) . . . . ? C7 N1 C8 C18 -93.4(6) . . . . ? Re1 N1 C8 C18 89.2(5) . . . . ? C7 N1 C8 C9 147.4(5) . . . . ? Re1 N1 C8 C9 -30.0(5) . . . . ? C10 N2 C9 C8 152.5(5) . . . . ? Re1 N2 C9 C8 -32.6(5) . . . . ? N1 C8 C9 N2 39.8(6) . . . . ? C17 C8 C9 N2 160.7(5) . . . . ? C18 C8 C9 N2 -77.0(6) . . . . ? C9 N2 C10 C11 167.7(5) . . . . ? Re1 N2 C10 C11 -6.6(8) . . . . ? N2 C10 C11 C12 178.7(6) . . . . ? N2 C10 C11 C16 -7.6(9) . . . . ? C16 C11 C12 C13 -1.0(9) . . . . ? C10 C11 C12 C13 173.0(6) . . . . ? C11 C12 C13 C14 -0.3(10) . . . . ? C12 C13 C14 C15 0.9(11) . . . . ? C13 C14 C15 C16 -0.2(11) . . . . ? Re1 O2 C16 C15 -173.8(4) . . . . ? Re1 O2 C16 C11 6.7(8) . . . . ? C14 C15 C16 O2 179.4(6) . . . . ? C14 C15 C16 C11 -1.1(9) . . . . ? C12 C11 C16 O2 -178.9(5) . . . . ? C10 C11 C16 O2 7.6(9) . . . . ? C12 C11 C16 C15 1.7(8) . . . . ? C10 C11 C16 C15 -171.9(6) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 2.699 _refine_diff_density_min -1.379 _refine_diff_density_rms 0.144 _database_code_depnum_ccdc_archive 'CCDC 933551' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_dar91c _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H18 N3 O3 Re S' _exptl_crystal_recrystallization_method ? _chemical_melting_point ? _exptl_crystal_description Prism _exptl_crystal_colour Green _diffrn_ambient_temperature 173(2) _chemical_formula_weight 554.62 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' N N 0.0061 0.0033 '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_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.920(4) _cell_length_b 9.487(4) _cell_length_c 11.657(5) _cell_angle_alpha 95.882(5) _cell_angle_beta 96.864(4) _cell_angle_gamma 103.701(4) _cell_volume 942.8(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1797 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 20.3 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.954 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 6.580 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.62 _exptl_absorpt_correction_T_max 0.88 _exptl_absorpt_process_details ; Data were corrected for decay and absorption using the program TWINABS (Sheldrick, G. M. (1996). TWINABS. Version 2008/4. University of G\"ottingen, Germany). ; _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 4287 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4287 _reflns_number_gt 3856 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2008)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2008)' _computing_data_reduction 'APEX2 (Bruker AXS, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-SEED, Barbour, 2001' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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. The data crystal was a non- merohedral twin with two major domains. The data was processed using Cell_now and TWINABS, and all refinements were carried out using the HKLF4 format data. ; _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^)+(0.0432P)^2^+0.0000P] 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 4287 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0358 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0733 _refine_ls_wR_factor_gt 0.0713 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 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 0.617821(19) 0.734678(18) 0.297022(15) 0.02251(7) Uani 1 1 d . . . S1 S 0.98092(15) 0.72973(17) 0.01790(12) 0.0397(3) Uani 1 1 d . . . O1 O 0.7912(4) 0.8098(4) 0.4296(3) 0.0288(7) Uani 1 1 d . . . O2 O 0.6610(3) 0.5404(3) 0.3224(3) 0.0237(7) Uani 1 1 d . . . O3 O 0.5872(4) 0.8874(4) 0.2460(3) 0.0365(8) Uani 1 1 d . . . N1 N 0.4502(4) 0.7193(4) 0.4061(3) 0.0230(8) Uani 1 1 d . . . N2 N 0.4251(4) 0.5958(4) 0.1916(3) 0.0246(8) Uani 1 1 d . . . N3 N 0.7819(5) 0.7300(4) 0.1841(4) 0.0299(9) Uani 1 1 d . . . C1 C 0.7755(5) 0.8482(4) 0.5392(4) 0.0238(9) Uani 1 1 d . . . C2 C 0.9129(5) 0.9033(5) 0.6185(4) 0.0267(10) Uani 1 1 d . . . H2 H 1.0107 0.9114 0.5917 0.032 Uiso 1 1 calc R . . C3 C 0.9099(6) 0.9464(5) 0.7353(4) 0.0305(11) Uani 1 1 d . . . H3 H 1.0051 0.9833 0.7872 0.037 Uiso 1 1 calc R . . C4 C 0.7671(6) 0.9361(5) 0.7776(4) 0.0301(10) Uani 1 1 d . . . H4 H 0.7647 0.9655 0.8576 0.036 Uiso 1 1 calc R . . C5 C 0.6315(6) 0.8825(5) 0.7010(4) 0.0273(10) Uani 1 1 d . . . H5 H 0.5347 0.8760 0.7290 0.033 Uiso 1 1 calc R . . C6 C 0.6309(5) 0.8368(5) 0.5818(4) 0.0245(9) Uani 1 1 d . . . C7 C 0.4798(5) 0.7718(5) 0.5153(4) 0.0230(9) Uani 1 1 d . . . H7 H 0.3927 0.7669 0.5558 0.028 Uiso 1 1 calc R . . C8 C 0.2841(5) 0.6455(5) 0.3492(4) 0.0244(9) Uani 1 1 d . . . C9 C 0.2855(5) 0.6426(5) 0.2171(4) 0.0283(10) Uani 1 1 d . . . H9A H 0.1902 0.5731 0.1733 0.034 Uiso 1 1 calc R . . H9B H 0.2896 0.7411 0.1946 0.034 Uiso 1 1 calc R . . C10 C 0.4098(6) 0.4676(5) 0.1379(4) 0.0250(9) Uani 1 1 d . . . H10 H 0.3116 0.4184 0.0933 0.030 Uiso 1 1 calc R . . C11 C 0.5339(5) 0.3937(5) 0.1415(4) 0.0248(9) Uani 1 1 d . . . C12 C 0.5248(6) 0.2709(5) 0.0594(4) 0.0302(10) Uani 1 1 d . . . H12 H 0.4428 0.2438 -0.0048 0.036 Uiso 1 1 calc R . . C13 C 0.6332(6) 0.1904(6) 0.0713(5) 0.0357(12) Uani 1 1 d . . . H13 H 0.6277 0.1091 0.0147 0.043 Uiso 1 1 calc R . . C14 C 0.7517(6) 0.2286(6) 0.1669(5) 0.0348(12) Uani 1 1 d . . . H14 H 0.8274 0.1732 0.1744 0.042 Uiso 1 1 calc R . . C15 C 0.7610(5) 0.3446(5) 0.2504(4) 0.0284(10) Uani 1 1 d . . . H15 H 0.8406 0.3666 0.3162 0.034 Uiso 1 1 calc R . . C16 C 0.6539(5) 0.4309(5) 0.2394(4) 0.0230(9) Uani 1 1 d . . . C17 C 0.1666(6) 0.7273(6) 0.3876(5) 0.0339(11) Uani 1 1 d . . . H17A H 0.1539 0.7151 0.4686 0.051 Uiso 1 1 calc R . . H17B H 0.0660 0.6878 0.3373 0.051 Uiso 1 1 calc R . . H17C H 0.2046 0.8316 0.3815 0.051 Uiso 1 1 calc R . . C18 C 0.2441(6) 0.4883(5) 0.3804(4) 0.0290(10) Uani 1 1 d . . . H18A H 0.3196 0.4368 0.3541 0.044 Uiso 1 1 calc R . . H18B H 0.1389 0.4364 0.3417 0.044 Uiso 1 1 calc R . . H18C H 0.2483 0.4917 0.4650 0.044 Uiso 1 1 calc R . . C19 C 0.8648(5) 0.7298(5) 0.1149(4) 0.0266(10) Uani 1 1 d . . . 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 0.02025(10) 0.02294(10) 0.02369(11) 0.00432(7) 0.00574(7) 0.00241(7) S1 0.0230(6) 0.0630(9) 0.0292(7) -0.0006(6) 0.0080(5) 0.0042(6) O1 0.0233(16) 0.0326(18) 0.0269(18) -0.0033(14) 0.0064(13) 0.0021(14) O2 0.0215(16) 0.0247(16) 0.0233(16) 0.0023(13) 0.0029(12) 0.0033(13) O3 0.038(2) 0.0339(19) 0.039(2) 0.0116(16) 0.0143(16) 0.0058(16) N1 0.0191(18) 0.0228(19) 0.028(2) 0.0064(15) 0.0051(15) 0.0058(15) N2 0.0240(19) 0.032(2) 0.0193(19) 0.0065(16) 0.0015(15) 0.0095(16) N3 0.024(2) 0.034(2) 0.027(2) 0.0048(17) 0.0036(17) -0.0005(17) C1 0.028(2) 0.015(2) 0.028(2) 0.0038(17) 0.0072(18) 0.0029(17) C2 0.023(2) 0.021(2) 0.034(3) 0.0030(19) 0.0011(19) 0.0022(18) C3 0.030(3) 0.023(2) 0.033(3) 0.0020(19) -0.004(2) 0.0020(19) C4 0.039(3) 0.026(2) 0.024(2) 0.0027(19) 0.002(2) 0.007(2) C5 0.031(3) 0.021(2) 0.031(3) 0.0063(18) 0.008(2) 0.0054(19) C6 0.027(2) 0.019(2) 0.029(2) 0.0045(17) 0.0071(19) 0.0063(18) C7 0.022(2) 0.023(2) 0.024(2) 0.0039(17) 0.0062(18) 0.0046(17) C8 0.017(2) 0.025(2) 0.031(2) 0.0065(18) 0.0008(18) 0.0052(17) C9 0.022(2) 0.031(2) 0.034(3) 0.007(2) 0.0010(19) 0.0103(19) C10 0.029(2) 0.030(2) 0.015(2) 0.0049(18) 0.0011(17) 0.0050(19) C11 0.024(2) 0.024(2) 0.025(2) 0.0042(18) 0.0060(18) 0.0026(18) C12 0.034(3) 0.029(2) 0.027(3) 0.0063(19) 0.011(2) 0.003(2) C13 0.040(3) 0.034(3) 0.035(3) 0.002(2) 0.018(2) 0.009(2) C14 0.032(3) 0.036(3) 0.044(3) 0.010(2) 0.018(2) 0.016(2) C15 0.022(2) 0.037(3) 0.028(3) 0.008(2) 0.0075(18) 0.009(2) C16 0.021(2) 0.028(2) 0.021(2) 0.0053(18) 0.0085(17) 0.0045(18) C17 0.027(3) 0.039(3) 0.040(3) 0.010(2) 0.005(2) 0.015(2) C18 0.023(2) 0.026(2) 0.037(3) 0.007(2) 0.0024(19) 0.0039(19) C19 0.017(2) 0.032(3) 0.029(3) 0.0054(19) 0.0008(18) 0.0037(18) _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 O3 1.689(4) . ? Re1 O1 1.992(3) . ? Re1 O2 2.014(3) . ? Re1 N1 2.065(4) . ? Re1 N2 2.072(4) . ? Re1 N3 2.087(4) . ? S1 C19 1.622(5) . ? O1 C1 1.326(5) . ? O2 C16 1.329(5) . ? N1 C7 1.291(6) . ? N1 C8 1.518(6) . ? N2 C10 1.278(6) . ? N2 C9 1.470(6) . ? N3 C19 1.158(6) . ? C1 C2 1.399(6) . ? C1 C6 1.421(6) . ? C2 C3 1.386(7) . ? C2 H2 0.9500 . ? C3 C4 1.405(7) . ? C3 H3 0.9500 . ? C4 C5 1.370(7) . ? C4 H4 0.9500 . ? C5 C6 1.411(6) . ? C5 H5 0.9500 . ? C6 C7 1.434(6) . ? C7 H7 0.9500 . ? C8 C17 1.525(6) . ? C8 C9 1.539(7) . ? C8 C18 1.540(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.443(6) . ? C10 H10 0.9500 . ? C11 C12 1.409(6) . ? C11 C16 1.421(6) . ? C12 C13 1.370(7) . ? C12 H12 0.9500 . ? C13 C14 1.395(8) . ? C13 H13 0.9500 . ? C14 C15 1.373(7) . ? C14 H14 0.9500 . ? C15 C16 1.400(6) . ? C15 H15 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? 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 O3 Re1 O1 104.09(16) . . ? O3 Re1 O2 167.66(14) . . ? O1 Re1 O2 82.93(13) . . ? O3 Re1 N1 95.22(16) . . ? O1 Re1 N1 92.44(14) . . ? O2 Re1 N1 94.59(13) . . ? O3 Re1 N2 94.32(17) . . ? O1 Re1 N2 160.12(15) . . ? O2 Re1 N2 80.37(14) . . ? N1 Re1 N2 78.29(15) . . ? O3 Re1 N3 88.89(17) . . ? O1 Re1 N3 89.40(15) . . ? O2 Re1 N3 80.96(14) . . ? N1 Re1 N3 174.95(14) . . ? N2 Re1 N3 98.51(15) . . ? C1 O1 Re1 125.8(3) . . ? C16 O2 Re1 125.8(3) . . ? C7 N1 C8 120.5(4) . . ? C7 N1 Re1 123.7(3) . . ? C8 N1 Re1 115.8(3) . . ? C10 N2 C9 119.4(4) . . ? C10 N2 Re1 129.4(3) . . ? C9 N2 Re1 108.3(3) . . ? C19 N3 Re1 174.7(4) . . ? O1 C1 C2 116.8(4) . . ? O1 C1 C6 125.1(4) . . ? C2 C1 C6 118.0(4) . . ? C3 C2 C1 121.6(4) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C2 C3 C4 120.6(4) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 118.6(5) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C4 C5 C6 122.1(5) . . ? C4 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C5 C6 C1 119.1(4) . . ? C5 C6 C7 115.3(4) . . ? C1 C6 C7 125.5(4) . . ? N1 C7 C6 126.5(4) . . ? N1 C7 H7 116.7 . . ? C6 C7 H7 116.7 . . ? N1 C8 C17 112.6(4) . . ? N1 C8 C9 105.6(4) . . ? C17 C8 C9 110.0(4) . . ? N1 C8 C18 107.7(4) . . ? C17 C8 C18 110.5(4) . . ? C9 C8 C18 110.3(4) . . ? N2 C9 C8 106.8(4) . . ? N2 C9 H9A 110.4 . . ? C8 C9 H9A 110.4 . . ? N2 C9 H9B 110.4 . . ? C8 C9 H9B 110.4 . . ? H9A C9 H9B 108.6 . . ? N2 C10 C11 123.4(4) . . ? N2 C10 H10 118.3 . . ? C11 C10 H10 118.3 . . ? C12 C11 C16 119.4(4) . . ? C12 C11 C10 120.8(4) . . ? C16 C11 C10 119.0(4) . . ? C13 C12 C11 120.6(5) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 119.6(5) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 121.2(5) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C14 C15 C16 120.5(5) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? O2 C16 C15 120.1(4) . . ? O2 C16 C11 121.3(4) . . ? C15 C16 C11 118.5(4) . . ? C8 C17 H17A 109.5 . . ? C8 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C8 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C8 C18 H18A 109.5 . . ? C8 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C8 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N3 C19 S1 179.9(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 O3 Re1 O1 C1 88.0(4) . . . . ? O2 Re1 O1 C1 -102.3(3) . . . . ? N1 Re1 O1 C1 -8.0(4) . . . . ? N2 Re1 O1 C1 -69.3(5) . . . . ? N3 Re1 O1 C1 176.7(4) . . . . ? O3 Re1 O2 C16 -17.7(8) . . . . ? O1 Re1 O2 C16 -143.2(3) . . . . ? N1 Re1 O2 C16 124.9(3) . . . . ? N2 Re1 O2 C16 47.6(3) . . . . ? N3 Re1 O2 C16 -52.7(3) . . . . ? O3 Re1 N1 C7 -94.9(4) . . . . ? O1 Re1 N1 C7 9.5(4) . . . . ? O2 Re1 N1 C7 92.6(4) . . . . ? N2 Re1 N1 C7 171.7(4) . . . . ? N3 Re1 N1 C7 120.7(16) . . . . ? O3 Re1 N1 C8 83.1(3) . . . . ? O1 Re1 N1 C8 -172.5(3) . . . . ? O2 Re1 N1 C8 -89.4(3) . . . . ? N2 Re1 N1 C8 -10.3(3) . . . . ? N3 Re1 N1 C8 -61.3(17) . . . . ? O3 Re1 N2 C10 141.0(4) . . . . ? O1 Re1 N2 C10 -61.0(6) . . . . ? O2 Re1 N2 C10 -27.8(4) . . . . ? N1 Re1 N2 C10 -124.5(4) . . . . ? N3 Re1 N2 C10 51.5(4) . . . . ? O3 Re1 N2 C9 -58.6(3) . . . . ? O1 Re1 N2 C9 99.4(4) . . . . ? O2 Re1 N2 C9 132.6(3) . . . . ? N1 Re1 N2 C9 35.8(3) . . . . ? N3 Re1 N2 C9 -148.1(3) . . . . ? O3 Re1 N3 C19 -44(4) . . . . ? O1 Re1 N3 C19 -148(4) . . . . ? O2 Re1 N3 C19 129(4) . . . . ? N1 Re1 N3 C19 100(5) . . . . ? N2 Re1 N3 C19 50(4) . . . . ? Re1 O1 C1 C2 -177.8(3) . . . . ? Re1 O1 C1 C6 2.6(6) . . . . ? O1 C1 C2 C3 -179.8(4) . . . . ? C6 C1 C2 C3 -0.3(7) . . . . ? C1 C2 C3 C4 -0.1(7) . . . . ? C2 C3 C4 C5 0.0(7) . . . . ? C3 C4 C5 C6 0.5(7) . . . . ? C4 C5 C6 C1 -0.8(7) . . . . ? C4 C5 C6 C7 174.9(4) . . . . ? O1 C1 C6 C5 -179.7(4) . . . . ? C2 C1 C6 C5 0.7(6) . . . . ? O1 C1 C6 C7 5.0(7) . . . . ? C2 C1 C6 C7 -174.5(4) . . . . ? C8 N1 C7 C6 176.3(4) . . . . ? Re1 N1 C7 C6 -5.8(6) . . . . ? C5 C6 C7 N1 -178.5(4) . . . . ? C1 C6 C7 N1 -3.1(7) . . . . ? C7 N1 C8 C17 42.2(6) . . . . ? Re1 N1 C8 C17 -135.9(3) . . . . ? C7 N1 C8 C9 162.3(4) . . . . ? Re1 N1 C8 C9 -15.8(4) . . . . ? C7 N1 C8 C18 -79.9(5) . . . . ? Re1 N1 C8 C18 102.1(4) . . . . ? C10 N2 C9 C8 107.8(5) . . . . ? Re1 N2 C9 C8 -54.9(4) . . . . ? N1 C8 C9 N2 44.5(5) . . . . ? C17 C8 C9 N2 166.4(4) . . . . ? C18 C8 C9 N2 -71.6(5) . . . . ? C9 N2 C10 C11 -159.1(4) . . . . ? Re1 N2 C10 C11 -0.6(7) . . . . ? N2 C10 C11 C12 -163.9(4) . . . . ? N2 C10 C11 C16 26.0(7) . . . . ? C16 C11 C12 C13 -2.1(7) . . . . ? C10 C11 C12 C13 -172.1(4) . . . . ? C11 C12 C13 C14 1.4(7) . . . . ? C12 C13 C14 C15 0.7(8) . . . . ? C13 C14 C15 C16 -2.1(8) . . . . ? Re1 O2 C16 C15 143.4(3) . . . . ? Re1 O2 C16 C11 -40.0(5) . . . . ? C14 C15 C16 O2 178.0(4) . . . . ? C14 C15 C16 C11 1.4(7) . . . . ? C12 C11 C16 O2 -175.9(4) . . . . ? C10 C11 C16 O2 -5.7(6) . . . . ? C12 C11 C16 C15 0.7(7) . . . . ? C10 C11 C16 C15 170.9(4) . . . . ? Re1 N3 C19 S1 39(100) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 2.538 _refine_diff_density_min -0.893 _refine_diff_density_rms 0.153 _database_code_depnum_ccdc_archive 'CCDC 933552' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_dar105acn2 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H33 N3 O2 P Re S' _exptl_crystal_recrystallization_method ? _chemical_melting_point ? _exptl_crystal_description Plate _exptl_crystal_colour Red _diffrn_ambient_temperature 173(2) _chemical_formula_weight 800.89 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' N N 0.0061 0.0033 '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' P P 0.1023 0.0942 '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 'C 2/c' _symmetry_int_tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 39.067(8) _cell_length_b 8.7460(18) _cell_length_c 19.104(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.644(2) _cell_angle_gamma 90.00 _cell_volume 6469(2) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8352 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 26.8 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3184 _exptl_absorpt_coefficient_mu 3.909 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.66 _exptl_absorpt_correction_T_max 0.93 _exptl_absorpt_process_details ; Data were corrected for decay and absorption using the program SADABS (Sheldrick, G. M. (2003). SADABS. Version 2.10. University of G\"ottingen, Germany). ; _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 35970 _diffrn_reflns_av_R_equivalents 0.0607 _diffrn_reflns_av_sigmaI/netI 0.0543 _diffrn_reflns_limit_h_min -50 _diffrn_reflns_limit_h_max 50 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.49 _reflns_number_total 7390 _reflns_number_gt 5170 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2008)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2008)' _computing_data_reduction 'APEX2 (Bruker AXS, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-SEED, Barbour, 2001' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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. Several crystals were examined and three data sets collected. While all crystals showed some non-merohedral twinning, the final crystal could be treated as single, though some residual electron density and the trend Fo>Fc for the worst fitting reflections may indicate the contribution from such twinning. A very strong sub-cell also may have confused the attempted corrections. ; _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^)+(0.0000P)^2^+120.9669P] 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 7390 _refine_ls_number_parameters 408 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0830 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1248 _refine_ls_wR_factor_gt 0.1174 _refine_ls_goodness_of_fit_ref 1.174 _refine_ls_restrained_S_all 1.174 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.107324(8) 0.00269(4) 0.030434(16) 0.03209(10) Uani 1 1 d . . . S1 S 0.02881(7) 0.2511(4) -0.15402(18) 0.0804(11) Uani 1 1 d . . . P1 P 0.15425(5) -0.1294(3) 0.10204(10) 0.0278(4) Uani 1 1 d . . . O1 O 0.14476(14) 0.0595(7) -0.0286(3) 0.0346(13) Uani 1 1 d . . . O2 O 0.11133(13) 0.1837(7) 0.0968(3) 0.0352(13) Uani 1 1 d . . . N1 N 0.09289(19) -0.1802(9) -0.0316(4) 0.0434(18) Uani 1 1 d . . . N2 N 0.06808(17) -0.0782(9) 0.0805(4) 0.0451(19) Uani 1 1 d . . . N3 N 0.0727(2) 0.1346(10) -0.0383(5) 0.055(2) Uani 1 1 d . . . C1 C 0.1548(2) -0.0193(10) -0.0812(4) 0.0375(19) Uani 1 1 d . . . C2 C 0.1858(2) 0.0273(11) -0.1055(4) 0.046(2) Uani 1 1 d . . . H2 H 0.1991 0.1085 -0.0827 0.055 Uiso 1 1 calc R . . C3 C 0.1967(3) -0.0460(13) -0.1628(5) 0.059(3) Uani 1 1 d . . . H3 H 0.2178 -0.0163 -0.1785 0.070 Uiso 1 1 calc R . . C4 C 0.1770(3) -0.1632(12) -0.1980(5) 0.062(3) Uani 1 1 d . . . H4 H 0.1842 -0.2094 -0.2386 0.074 Uiso 1 1 calc R . . C5 C 0.1476(3) -0.2110(12) -0.1737(5) 0.056(3) Uani 1 1 d . . . H5 H 0.1346 -0.2913 -0.1980 0.067 Uiso 1 1 calc R . . C6 C 0.1357(3) -0.1458(11) -0.1141(4) 0.045(2) Uani 1 1 d . . . C7 C 0.1059(2) -0.2151(11) -0.0891(5) 0.049(2) Uani 1 1 d . . . H7 H 0.0947 -0.2943 -0.1175 0.058 Uiso 1 1 calc R . . C8 C 0.0596(3) -0.2594(12) -0.0131(6) 0.062(3) Uani 1 1 d . . . C9 C 0.0585(3) -0.2370(12) 0.0630(6) 0.059(3) Uani 1 1 d . . . H9A H 0.0351 -0.2583 0.0746 0.070 Uiso 1 1 calc R . . H9B H 0.0749 -0.3076 0.0907 0.070 Uiso 1 1 calc R . . C10 C 0.0522(2) -0.0066(13) 0.1265(5) 0.054(3) Uani 1 1 d . . . H10 H 0.0334 -0.0579 0.1430 0.065 Uiso 1 1 calc R . . C11 C 0.0604(2) 0.1402(12) 0.1540(5) 0.042(2) Uani 1 1 d . . . C12 C 0.0394(2) 0.1991(16) 0.2024(5) 0.062(3) Uani 1 1 d . . . H12 H 0.0208 0.1387 0.2141 0.075 Uiso 1 1 calc R . . C13 C 0.0449(2) 0.3398(15) 0.2329(5) 0.060(3) Uani 1 1 d . . . H13 H 0.0302 0.3776 0.2649 0.072 Uiso 1 1 calc R . . C14 C 0.0724(2) 0.4259(14) 0.2157(5) 0.053(3) Uani 1 1 d . . . H14 H 0.0766 0.5236 0.2367 0.063 Uiso 1 1 calc R . . C15 C 0.0936(2) 0.3747(11) 0.1696(4) 0.040(2) Uani 1 1 d . . . H15 H 0.1119 0.4380 0.1585 0.048 Uiso 1 1 calc R . . C16 C 0.0888(2) 0.2295(11) 0.1382(4) 0.038(2) Uani 1 1 d . . . C17 C 0.0601(3) -0.4305(14) -0.0302(6) 0.073(3) Uani 1 1 d . . . H17A H 0.0814 -0.4763 -0.0060 0.109 Uiso 1 1 calc R . . H17B H 0.0592 -0.4444 -0.0813 0.109 Uiso 1 1 calc R . . H17C H 0.0401 -0.4803 -0.0142 0.109 Uiso 1 1 calc R . . C18 C 0.0273(3) -0.1838(14) -0.0553(6) 0.071(3) Uani 1 1 d . . . H18A H 0.0064 -0.2352 -0.0441 0.106 Uiso 1 1 calc R . . H18B H 0.0285 -0.1930 -0.1060 0.106 Uiso 1 1 calc R . . H18C H 0.0264 -0.0755 -0.0425 0.106 Uiso 1 1 calc R . . C19 C 0.0547(2) 0.1853(13) -0.0852(6) 0.056(3) Uani 1 1 d . . . C20 C 0.19307(17) -0.0141(10) 0.1280(4) 0.0276(16) Uani 1 1 d . . . C21 C 0.22210(19) -0.0791(10) 0.1666(4) 0.0330(18) Uani 1 1 d . . . H21 H 0.2218 -0.1842 0.1790 0.040 Uiso 1 1 calc R . . C22 C 0.25154(18) 0.0068(11) 0.1874(4) 0.0357(18) Uani 1 1 d . . . H22 H 0.2711 -0.0390 0.2142 0.043 Uiso 1 1 calc R . . C23 C 0.2523(2) 0.1594(11) 0.1690(4) 0.038(2) Uani 1 1 d . . . H23 H 0.2725 0.2184 0.1826 0.046 Uiso 1 1 calc R . . C24 C 0.2237(2) 0.2262(11) 0.1309(4) 0.041(2) Uani 1 1 d . . . H24 H 0.2243 0.3311 0.1182 0.050 Uiso 1 1 calc R . . C25 C 0.1939(2) 0.1404(11) 0.1110(4) 0.040(2) Uani 1 1 d . . . H25 H 0.1741 0.1876 0.0857 0.048 Uiso 1 1 calc R . . C26 C 0.14599(19) -0.2110(9) 0.1859(4) 0.0279(16) Uani 1 1 d . . . C27 C 0.1619(2) -0.3413(10) 0.2160(4) 0.0341(18) Uani 1 1 d . . . H27 H 0.1775 -0.3966 0.1913 0.041 Uiso 1 1 calc R . . C28 C 0.1554(2) -0.3922(10) 0.2821(4) 0.039(2) Uani 1 1 d . . . H28 H 0.1666 -0.4808 0.3027 0.047 Uiso 1 1 calc R . . C29 C 0.1321(2) -0.3119(11) 0.3179(4) 0.043(2) Uani 1 1 d . . . H29 H 0.1272 -0.3467 0.3626 0.051 Uiso 1 1 calc R . . C30 C 0.1161(2) -0.1825(11) 0.2884(4) 0.041(2) Uani 1 1 d . . . H30 H 0.1001 -0.1288 0.3125 0.049 Uiso 1 1 calc R . . C31 C 0.1235(2) -0.1301(11) 0.2233(4) 0.0366(19) Uani 1 1 d . . . H31 H 0.1131 -0.0385 0.2040 0.044 Uiso 1 1 calc R . . C32 C 0.1703(2) -0.2888(10) 0.0534(4) 0.0316(18) Uani 1 1 d . . . C33 C 0.1519(2) -0.4243(10) 0.0458(4) 0.0360(19) Uani 1 1 d . . . H33 H 0.1323 -0.4373 0.0699 0.043 Uiso 1 1 calc R . . C34 C 0.1615(2) -0.5408(11) 0.0036(4) 0.044(2) Uani 1 1 d . . . H34 H 0.1486 -0.6333 -0.0008 0.053 Uiso 1 1 calc R . . C35 C 0.1900(2) -0.5227(12) -0.0323(4) 0.047(2) Uani 1 1 d . . . H35 H 0.1966 -0.6027 -0.0613 0.057 Uiso 1 1 calc R . . C36 C 0.2086(2) -0.3879(11) -0.0257(4) 0.043(2) Uani 1 1 d . . . H36 H 0.2280 -0.3751 -0.0503 0.052 Uiso 1 1 calc R . . C37 C 0.19893(19) -0.2714(11) 0.0171(4) 0.0351(19) Uani 1 1 d . . . H37 H 0.2118 -0.1790 0.0217 0.042 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 0.02437(14) 0.03614(17) 0.03452(16) 0.00594(16) -0.00066(10) -0.00433(16) S1 0.0455(15) 0.108(3) 0.083(2) 0.055(2) -0.0089(14) -0.0093(16) P1 0.0247(9) 0.0340(12) 0.0249(9) 0.0022(8) 0.0040(7) -0.0025(9) O1 0.042(3) 0.037(3) 0.025(3) -0.001(2) 0.007(2) -0.012(3) O2 0.029(3) 0.036(3) 0.042(3) 0.001(3) 0.009(2) -0.004(3) N1 0.040(4) 0.047(5) 0.039(4) 0.001(4) -0.009(3) -0.002(4) N2 0.027(4) 0.046(5) 0.063(5) 0.016(4) 0.007(3) -0.004(3) N3 0.036(4) 0.052(5) 0.072(6) 0.017(5) -0.008(4) -0.007(4) C1 0.060(5) 0.028(5) 0.024(4) 0.005(3) 0.003(3) 0.004(4) C2 0.063(6) 0.041(6) 0.035(4) 0.004(4) 0.015(4) 0.005(5) C3 0.080(7) 0.057(7) 0.044(5) 0.009(5) 0.028(5) 0.019(6) C4 0.109(10) 0.043(6) 0.034(5) -0.003(5) 0.017(6) 0.022(6) C5 0.085(8) 0.048(6) 0.033(5) -0.009(4) -0.001(5) 0.002(6) C6 0.065(6) 0.036(5) 0.028(4) 0.000(4) -0.011(4) 0.008(5) C7 0.053(6) 0.041(6) 0.046(5) 0.002(4) -0.016(4) -0.006(5) C8 0.059(6) 0.043(6) 0.073(7) 0.011(5) -0.032(5) -0.027(5) C9 0.048(6) 0.052(7) 0.078(8) 0.008(6) 0.014(5) -0.003(5) C10 0.021(4) 0.070(7) 0.072(6) 0.021(6) 0.015(4) 0.002(5) C11 0.028(4) 0.057(6) 0.043(5) 0.008(5) 0.007(4) -0.001(4) C12 0.024(4) 0.108(10) 0.057(6) 0.011(7) 0.015(4) 0.002(5) C13 0.035(5) 0.099(10) 0.048(6) -0.010(6) 0.013(4) 0.012(6) C14 0.040(5) 0.079(8) 0.039(5) -0.017(5) 0.005(4) -0.004(5) C15 0.038(5) 0.048(6) 0.036(4) -0.005(4) 0.010(4) 0.001(4) C16 0.023(4) 0.054(6) 0.037(4) 0.007(4) 0.006(3) 0.005(4) C17 0.071(8) 0.066(8) 0.078(8) -0.015(7) 0.002(6) -0.013(7) C18 0.046(6) 0.079(9) 0.078(8) -0.003(7) -0.026(5) -0.010(6) C19 0.032(5) 0.064(7) 0.073(7) 0.032(6) 0.007(5) -0.006(5) C20 0.022(3) 0.035(5) 0.027(3) -0.003(4) 0.005(3) 0.003(4) C21 0.032(4) 0.036(5) 0.031(4) 0.001(4) 0.006(3) -0.002(4) C22 0.023(3) 0.048(5) 0.034(4) 0.000(4) -0.002(3) 0.002(4) C23 0.029(4) 0.047(6) 0.038(4) -0.010(4) 0.005(3) -0.012(4) C24 0.037(5) 0.043(5) 0.044(5) 0.000(4) 0.004(4) -0.010(4) C25 0.034(4) 0.045(6) 0.041(5) 0.001(4) 0.004(4) -0.005(4) C26 0.027(4) 0.033(4) 0.024(4) 0.003(3) 0.004(3) -0.005(3) C27 0.028(4) 0.036(5) 0.037(4) 0.001(4) 0.000(3) -0.005(4) C28 0.043(5) 0.040(5) 0.033(4) 0.011(4) -0.001(4) -0.001(4) C29 0.048(5) 0.050(6) 0.030(4) 0.011(4) 0.002(4) -0.010(4) C30 0.037(5) 0.057(6) 0.029(4) -0.005(4) 0.008(4) 0.000(4) C31 0.036(4) 0.043(5) 0.029(4) 0.004(4) 0.002(3) 0.003(4) C32 0.031(4) 0.039(5) 0.025(4) 0.002(3) 0.003(3) 0.001(4) C33 0.042(5) 0.039(5) 0.027(4) 0.002(4) 0.004(3) -0.012(4) C34 0.055(6) 0.039(5) 0.035(5) -0.002(4) -0.006(4) -0.007(4) C35 0.050(5) 0.055(7) 0.035(4) -0.011(4) -0.001(4) 0.012(5) C36 0.040(5) 0.057(6) 0.034(5) -0.008(4) 0.009(4) 0.004(5) C37 0.025(4) 0.046(5) 0.035(4) -0.003(4) 0.005(3) -0.003(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 O2 2.022(6) . ? Re1 O1 2.024(5) . ? Re1 N1 2.025(8) . ? Re1 N2 2.038(7) . ? Re1 N3 2.100(8) . ? Re1 P1 2.429(2) . ? S1 C19 1.652(10) . ? P1 C26 1.822(7) . ? P1 C32 1.832(8) . ? P1 C20 1.833(8) . ? O1 C1 1.320(9) . ? O2 C16 1.321(9) . ? N1 C7 1.307(12) . ? N1 C8 1.555(12) . ? N2 C10 1.302(12) . ? N2 C9 1.464(13) . ? N3 C19 1.152(11) . ? C1 C2 1.414(12) . ? C1 C6 1.432(12) . ? C2 C3 1.383(12) . ? C2 H2 0.9500 . ? C3 C4 1.396(15) . ? C3 H3 0.9500 . ? C4 C5 1.362(15) . ? C4 H4 0.9500 . ? C5 C6 1.407(13) . ? C5 H5 0.9500 . ? C6 C7 1.447(13) . ? C7 H7 0.9500 . ? C8 C9 1.475(15) . ? C8 C17 1.533(15) . ? C8 C18 1.552(14) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.407(14) . ? C10 H10 0.9500 . ? C11 C12 1.414(13) . ? C11 C16 1.420(12) . ? C12 C13 1.365(16) . ? C12 H12 0.9500 . ? C13 C14 1.388(14) . ? C13 H13 0.9500 . ? C14 C15 1.362(12) . ? C14 H14 0.9500 . ? C15 C16 1.406(13) . ? C15 H15 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C20 C21 1.389(10) . ? C20 C25 1.392(12) . ? C21 C22 1.387(11) . ? C21 H21 0.9500 . ? C22 C23 1.381(12) . ? C22 H22 0.9500 . ? C23 C24 1.380(12) . ? C23 H23 0.9500 . ? C24 C25 1.394(11) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C27 1.386(11) . ? C26 C31 1.395(11) . ? C27 C28 1.396(11) . ? C27 H27 0.9500 . ? C28 C29 1.398(12) . ? C28 H28 0.9500 . ? C29 C30 1.375(13) . ? C29 H29 0.9500 . ? C30 C31 1.392(11) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? C32 C33 1.385(11) . ? C32 C37 1.400(10) . ? C33 C34 1.381(12) . ? C33 H33 0.9500 . ? C34 C35 1.391(13) . ? C34 H34 0.9500 . ? C35 C36 1.383(13) . ? C35 H35 0.9500 . ? C36 C37 1.390(12) . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? 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 O2 Re1 O1 99.0(2) . . ? O2 Re1 N1 167.9(3) . . ? O1 Re1 N1 91.9(3) . . ? O2 Re1 N2 88.7(3) . . ? O1 Re1 N2 172.2(3) . . ? N1 Re1 N2 80.3(3) . . ? O2 Re1 N3 87.2(3) . . ? O1 Re1 N3 88.3(3) . . ? N1 Re1 N3 87.8(3) . . ? N2 Re1 N3 91.3(3) . . ? O2 Re1 P1 91.68(16) . . ? O1 Re1 P1 83.29(17) . . ? N1 Re1 P1 94.8(2) . . ? N2 Re1 P1 97.4(2) . . ? N3 Re1 P1 171.2(2) . . ? C26 P1 C32 105.1(4) . . ? C26 P1 C20 102.4(3) . . ? C32 P1 C20 103.2(3) . . ? C26 P1 Re1 118.2(3) . . ? C32 P1 Re1 111.1(2) . . ? C20 P1 Re1 115.2(3) . . ? C1 O1 Re1 127.3(5) . . ? C16 O2 Re1 127.6(5) . . ? C7 N1 C8 121.1(8) . . ? C7 N1 Re1 124.5(7) . . ? C8 N1 Re1 113.3(6) . . ? C10 N2 C9 118.8(8) . . ? C10 N2 Re1 127.2(7) . . ? C9 N2 Re1 114.0(6) . . ? C19 N3 Re1 166.8(10) . . ? O1 C1 C2 117.0(8) . . ? O1 C1 C6 123.2(8) . . ? C2 C1 C6 119.8(8) . . ? C3 C2 C1 119.5(9) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 120.9(10) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 119.7(9) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 122.4(10) . . ? C4 C5 H5 118.8 . . ? C6 C5 H5 118.8 . . ? C5 C6 C1 117.3(9) . . ? C5 C6 C7 117.7(9) . . ? C1 C6 C7 125.0(8) . . ? N1 C7 C6 126.8(9) . . ? N1 C7 H7 116.6 . . ? C6 C7 H7 116.6 . . ? C9 C8 C17 110.0(9) . . ? C9 C8 C18 109.2(10) . . ? C17 C8 C18 109.8(8) . . ? C9 C8 N1 107.3(7) . . ? C17 C8 N1 110.6(10) . . ? C18 C8 N1 109.9(8) . . ? N2 C9 C8 108.1(8) . . ? N2 C9 H9A 110.1 . . ? C8 C9 H9A 110.1 . . ? N2 C9 H9B 110.1 . . ? C8 C9 H9B 110.1 . . ? H9A C9 H9B 108.4 . . ? N2 C10 C11 125.9(8) . . ? N2 C10 H10 117.1 . . ? C11 C10 H10 117.1 . . ? C10 C11 C12 116.9(9) . . ? C10 C11 C16 124.6(8) . . ? C12 C11 C16 118.5(10) . . ? C13 C12 C11 122.4(10) . . ? C13 C12 H12 118.8 . . ? C11 C12 H12 118.8 . . ? C12 C13 C14 118.1(9) . . ? C12 C13 H13 121.0 . . ? C14 C13 H13 121.0 . . ? C15 C14 C13 122.1(10) . . ? C15 C14 H14 119.0 . . ? C13 C14 H14 119.0 . . ? C14 C15 C16 121.0(9) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? O2 C16 C15 117.9(8) . . ? O2 C16 C11 124.2(9) . . ? C15 C16 C11 118.0(8) . . ? C8 C17 H17A 109.5 . . ? C8 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C8 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C8 C18 H18A 109.5 . . ? C8 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C8 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N3 C19 S1 177.6(12) . . ? C21 C20 C25 118.6(7) . . ? C21 C20 P1 120.4(6) . . ? C25 C20 P1 121.0(6) . . ? C22 C21 C20 121.2(8) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C23 C22 C21 119.7(7) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? C24 C23 C22 120.0(8) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C23 C24 C25 120.3(9) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C20 C25 C24 120.2(8) . . ? C20 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C27 C26 C31 119.0(7) . . ? C27 C26 P1 124.3(6) . . ? C31 C26 P1 116.6(6) . . ? C26 C27 C28 120.7(8) . . ? C26 C27 H27 119.7 . . ? C28 C27 H27 119.7 . . ? C27 C28 C29 119.5(8) . . ? C27 C28 H28 120.2 . . ? C29 C28 H28 120.2 . . ? C30 C29 C28 120.1(8) . . ? C30 C29 H29 119.9 . . ? C28 C29 H29 119.9 . . ? C29 C30 C31 120.1(8) . . ? C29 C30 H30 120.0 . . ? C31 C30 H30 120.0 . . ? C30 C31 C26 120.6(8) . . ? C30 C31 H31 119.7 . . ? C26 C31 H31 119.7 . . ? C33 C32 C37 118.6(8) . . ? C33 C32 P1 119.7(6) . . ? C37 C32 P1 121.2(7) . . ? C34 C33 C32 121.0(8) . . ? C34 C33 H33 119.5 . . ? C32 C33 H33 119.5 . . ? C33 C34 C35 120.0(9) . . ? C33 C34 H34 120.0 . . ? C35 C34 H34 120.0 . . ? C36 C35 C34 119.9(9) . . ? C36 C35 H35 120.1 . . ? C34 C35 H35 120.1 . . ? C35 C36 C37 119.8(8) . . ? C35 C36 H36 120.1 . . ? C37 C36 H36 120.1 . . ? C36 C37 C32 120.6(8) . . ? C36 C37 H37 119.7 . . ? C32 C37 H37 119.7 . . ? 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 O2 Re1 P1 C26 73.4(3) . . . . ? O1 Re1 P1 C26 172.3(3) . . . . ? N1 Re1 P1 C26 -96.3(4) . . . . ? N2 Re1 P1 C26 -15.5(4) . . . . ? N3 Re1 P1 C26 156.2(17) . . . . ? O2 Re1 P1 C32 -164.9(3) . . . . ? O1 Re1 P1 C32 -66.1(3) . . . . ? N1 Re1 P1 C32 25.3(4) . . . . ? N2 Re1 P1 C32 106.1(4) . . . . ? N3 Re1 P1 C32 -82.2(17) . . . . ? O2 Re1 P1 C20 -48.0(3) . . . . ? O1 Re1 P1 C20 50.8(3) . . . . ? N1 Re1 P1 C20 142.2(3) . . . . ? N2 Re1 P1 C20 -137.0(3) . . . . ? N3 Re1 P1 C20 34.7(17) . . . . ? O2 Re1 O1 C1 178.7(6) . . . . ? N1 Re1 O1 C1 -6.6(7) . . . . ? N2 Re1 O1 C1 -8(2) . . . . ? N3 Re1 O1 C1 -94.4(7) . . . . ? P1 Re1 O1 C1 88.0(6) . . . . ? O1 Re1 O2 C16 164.0(6) . . . . ? N1 Re1 O2 C16 10.0(16) . . . . ? N2 Re1 O2 C16 -15.1(7) . . . . ? N3 Re1 O2 C16 76.2(7) . . . . ? P1 Re1 O2 C16 -112.5(6) . . . . ? O2 Re1 N1 C7 150.1(11) . . . . ? O1 Re1 N1 C7 -4.2(7) . . . . ? N2 Re1 N1 C7 175.7(8) . . . . ? N3 Re1 N1 C7 84.0(8) . . . . ? P1 Re1 N1 C7 -87.6(7) . . . . ? O2 Re1 N1 C8 -18.4(16) . . . . ? O1 Re1 N1 C8 -172.7(6) . . . . ? N2 Re1 N1 C8 7.1(6) . . . . ? N3 Re1 N1 C8 -84.5(6) . . . . ? P1 Re1 N1 C8 103.9(6) . . . . ? O2 Re1 N2 C10 10.3(8) . . . . ? O1 Re1 N2 C10 -163.4(17) . . . . ? N1 Re1 N2 C10 -164.5(8) . . . . ? N3 Re1 N2 C10 -76.9(8) . . . . ? P1 Re1 N2 C10 101.8(8) . . . . ? O2 Re1 N2 C9 -167.1(7) . . . . ? O1 Re1 N2 C9 19(2) . . . . ? N1 Re1 N2 C9 18.1(6) . . . . ? N3 Re1 N2 C9 105.7(7) . . . . ? P1 Re1 N2 C9 -75.6(6) . . . . ? O2 Re1 N3 C19 167(3) . . . . ? O1 Re1 N3 C19 68(3) . . . . ? N1 Re1 N3 C19 -24(3) . . . . ? N2 Re1 N3 C19 -104(3) . . . . ? P1 Re1 N3 C19 84(4) . . . . ? Re1 O1 C1 C2 -167.9(6) . . . . ? Re1 O1 C1 C6 12.8(11) . . . . ? O1 C1 C2 C3 -176.7(8) . . . . ? C6 C1 C2 C3 2.5(13) . . . . ? C1 C2 C3 C4 1.5(14) . . . . ? C2 C3 C4 C5 -3.0(16) . . . . ? C3 C4 C5 C6 0.4(16) . . . . ? C4 C5 C6 C1 3.5(14) . . . . ? C4 C5 C6 C7 -174.3(9) . . . . ? O1 C1 C6 C5 174.3(8) . . . . ? C2 C1 C6 C5 -4.9(12) . . . . ? O1 C1 C6 C7 -8.1(13) . . . . ? C2 C1 C6 C7 172.6(8) . . . . ? C8 N1 C7 C6 177.0(8) . . . . ? Re1 N1 C7 C6 9.3(13) . . . . ? C5 C6 C7 N1 173.6(9) . . . . ? C1 C6 C7 N1 -3.9(15) . . . . ? C7 N1 C8 C9 160.8(9) . . . . ? Re1 N1 C8 C9 -30.2(10) . . . . ? C7 N1 C8 C17 40.8(12) . . . . ? Re1 N1 C8 C17 -150.2(7) . . . . ? C7 N1 C8 C18 -80.6(12) . . . . ? Re1 N1 C8 C18 88.4(9) . . . . ? C10 N2 C9 C8 142.3(9) . . . . ? Re1 N2 C9 C8 -40.1(10) . . . . ? C17 C8 C9 N2 163.8(8) . . . . ? C18 C8 C9 N2 -75.6(10) . . . . ? N1 C8 C9 N2 43.5(11) . . . . ? C9 N2 C10 C11 173.6(9) . . . . ? Re1 N2 C10 C11 -3.7(14) . . . . ? N2 C10 C11 C12 178.5(9) . . . . ? N2 C10 C11 C16 -3.6(15) . . . . ? C10 C11 C12 C13 179.7(10) . . . . ? C16 C11 C12 C13 1.7(15) . . . . ? C11 C12 C13 C14 -0.7(16) . . . . ? C12 C13 C14 C15 0.4(16) . . . . ? C13 C14 C15 C16 -1.3(15) . . . . ? Re1 O2 C16 C15 -167.8(6) . . . . ? Re1 O2 C16 C11 13.6(11) . . . . ? C14 C15 C16 O2 -176.5(8) . . . . ? C14 C15 C16 C11 2.2(13) . . . . ? C10 C11 C16 O2 -1.6(14) . . . . ? C12 C11 C16 O2 176.3(8) . . . . ? C10 C11 C16 C15 179.8(8) . . . . ? C12 C11 C16 C15 -2.4(12) . . . . ? Re1 N3 C19 S1 15(25) . . . . ? C26 P1 C20 C21 52.9(7) . . . . ? C32 P1 C20 C21 -56.1(7) . . . . ? Re1 P1 C20 C21 -177.4(5) . . . . ? C26 P1 C20 C25 -125.6(7) . . . . ? C32 P1 C20 C25 125.4(7) . . . . ? Re1 P1 C20 C25 4.1(7) . . . . ? C25 C20 C21 C22 -0.7(11) . . . . ? P1 C20 C21 C22 -179.2(6) . . . . ? C20 C21 C22 C23 -0.6(12) . . . . ? C21 C22 C23 C24 0.9(12) . . . . ? C22 C23 C24 C25 0.1(13) . . . . ? C21 C20 C25 C24 1.7(12) . . . . ? P1 C20 C25 C24 -179.8(6) . . . . ? C23 C24 C25 C20 -1.4(13) . . . . ? C32 P1 C26 C27 24.0(7) . . . . ? C20 P1 C26 C27 -83.5(7) . . . . ? Re1 P1 C26 C27 148.7(6) . . . . ? C32 P1 C26 C31 -159.7(6) . . . . ? C20 P1 C26 C31 92.7(6) . . . . ? Re1 P1 C26 C31 -35.1(7) . . . . ? C31 C26 C27 C28 0.7(12) . . . . ? P1 C26 C27 C28 176.9(6) . . . . ? C26 C27 C28 C29 0.9(12) . . . . ? C27 C28 C29 C30 -0.9(13) . . . . ? C28 C29 C30 C31 -0.8(13) . . . . ? C29 C30 C31 C26 2.4(13) . . . . ? C27 C26 C31 C30 -2.4(12) . . . . ? P1 C26 C31 C30 -178.9(6) . . . . ? C26 P1 C32 C33 51.5(7) . . . . ? C20 P1 C32 C33 158.4(6) . . . . ? Re1 P1 C32 C33 -77.5(7) . . . . ? C26 P1 C32 C37 -135.7(6) . . . . ? C20 P1 C32 C37 -28.7(7) . . . . ? Re1 P1 C32 C37 95.3(6) . . . . ? C37 C32 C33 C34 0.5(12) . . . . ? P1 C32 C33 C34 173.5(6) . . . . ? C32 C33 C34 C35 -0.4(13) . . . . ? C33 C34 C35 C36 0.0(13) . . . . ? C34 C35 C36 C37 0.3(13) . . . . ? C35 C36 C37 C32 -0.2(13) . . . . ? C33 C32 C37 C36 -0.2(12) . . . . ? P1 C32 C37 C36 -173.1(6) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 2.331 _refine_diff_density_min -4.120 _refine_diff_density_rms 0.147 _database_code_depnum_ccdc_archive 'CCDC 933553' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_DAR105e _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C38 H36 N6 O5 Re2 S2, 2(C2 H3 N)' _chemical_formula_sum 'C42 H42 N8 O5 Re2 S2' _chemical_melting_point ? _exptl_crystal_description Block _exptl_crystal_colour Purple _diffrn_ambient_temperature 173(2) _chemical_formula_weight 1175.36 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' N N 0.0061 0.0033 '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' P P 0.1023 0.0942 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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_int_tables_number 14 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 10.1169(13) _cell_length_b 16.397(2) _cell_length_c 13.1679(17) _cell_angle_alpha 90.00 _cell_angle_beta 95.155(2) _cell_angle_gamma 90.00 _cell_volume 2175.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4489 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 20.6 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.794 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 5.708 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.47 _exptl_absorpt_correction_T_max 0.67 _exptl_absorpt_process_details ; Data were corrected for decay and absorption using the program SADABS (Sheldrick, G. M. (2003). SADABS. Version 2.10. University of G\"ottingen, Germany). ; _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 25000 _diffrn_reflns_av_R_equivalents 0.0541 _diffrn_reflns_av_sigmaI/netI 0.0447 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 27.51 _reflns_number_total 4981 _reflns_number_gt 3448 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2008)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2008)' _computing_data_reduction 'APEX2 (Bruker AXS, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-SEED, Barbour, 2001' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.0324P)^2^+17.1546P] 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 4981 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0916 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.1389 _refine_ls_wR_factor_gt 0.1276 _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_restrained_S_all 1.155 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 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 0.63767(4) 0.05550(2) 0.94933(4) 0.05675(16) Uani 1 1 d . . . S1 S 0.9525(5) 0.2036(3) 0.7777(5) 0.156(2) Uani 1 1 d . . . O1 O 0.6672(6) 0.1206(4) 1.0781(6) 0.0588(17) Uani 1 1 d . . . O2 O 0.5127(6) 0.1318(4) 0.8694(5) 0.0567(17) Uani 1 1 d . . . O3 O 0.5000 0.0000 1.0000 0.053(2) Uani 1 2 d S . . N1 N 0.7610(9) -0.0348(6) 1.0090(8) 0.072(3) Uani 1 1 d . . . N2 N 0.6368(9) -0.0177(5) 0.8251(8) 0.066(2) Uani 1 1 d . . . N3 N 0.7965(11) 0.1222(6) 0.8941(7) 0.063(3) Uani 1 1 d . . . N4 N 0.6583(19) 0.4115(17) 0.8871(19) 0.213(11) Uani 1 1 d . . . C22 C 0.7027(10) 0.0886(7) 1.1696(9) 0.059(3) Uani 1 1 d . . . C2 C 0.6804(11) 0.1346(8) 1.2551(10) 0.073(3) Uani 1 1 d . . . H2 H 0.6387 0.1863 1.2457 0.088 Uiso 1 1 calc R . . C3 C 0.7170(12) 0.1078(9) 1.3534(10) 0.081(4) Uani 1 1 d . . . H3 H 0.7018 0.1403 1.4110 0.097 Uiso 1 1 calc R . . C4 C 0.7770(14) 0.0313(10) 1.3648(13) 0.094(4) Uani 1 1 d . . . H4 H 0.8011 0.0118 1.4319 0.112 Uiso 1 1 calc R . . C5 C 0.8027(13) -0.0169(10) 1.2842(12) 0.090(4) Uani 1 1 d . . . H5 H 0.8445 -0.0685 1.2947 0.108 Uiso 1 1 calc R . . C6 C 0.7651(10) 0.0123(7) 1.1847(10) 0.071(3) Uani 1 1 d . . . C7 C 0.7956(11) -0.0421(7) 1.1040(12) 0.077(4) Uani 1 1 d . . . H7 H 0.8475 -0.0886 1.1239 0.092 Uiso 1 1 calc R . . C8 C 0.7861(12) -0.1011(6) 0.9235(12) 0.083(4) Uani 1 1 d . . . C9 C 0.6756(14) -0.1038(9) 0.8499(12) 0.096(4) Uani 1 1 d . . . H9A H 0.6011 -0.1332 0.8773 0.115 Uiso 1 1 calc R . . H9B H 0.6992 -0.1324 0.7879 0.115 Uiso 1 1 calc R . . C10 C 0.6040(11) 0.0049(7) 0.7315(10) 0.067(3) Uani 1 1 d . . . H10 H 0.6237 -0.0319 0.6793 0.080 Uiso 1 1 calc R . . C11 C 0.5409(10) 0.0799(6) 0.6999(9) 0.062(3) Uani 1 1 d . . . C12 C 0.5192(12) 0.0943(8) 0.5935(9) 0.070(3) Uani 1 1 d . . . H12 H 0.5514 0.0558 0.5478 0.084 Uiso 1 1 calc R . . C13 C 0.4538(13) 0.1613(9) 0.5550(11) 0.085(4) Uani 1 1 d . . . H13 H 0.4412 0.1708 0.4836 0.102 Uiso 1 1 calc R . . C14 C 0.4065(11) 0.2151(9) 0.6236(11) 0.080(4) Uani 1 1 d . . . H14 H 0.3573 0.2613 0.5983 0.096 Uiso 1 1 calc R . . C15 C 0.4278(9) 0.2043(7) 0.7264(9) 0.061(3) Uani 1 1 d . . . H15 H 0.3936 0.2434 0.7705 0.074 Uiso 1 1 calc R . . C16 C 0.4975(9) 0.1385(6) 0.7680(8) 0.052(2) Uani 1 1 d . . . C17 C 0.7934(17) -0.1869(7) 0.9755(14) 0.118(6) Uani 1 1 d . . . H17A H 0.7175 -0.1938 1.0160 0.176 Uiso 1 1 calc R . . H17B H 0.8760 -0.1913 1.0201 0.176 Uiso 1 1 calc R . . H17C H 0.7913 -0.2293 0.9230 0.176 Uiso 1 1 calc R . . C18 C 0.9115(14) -0.0820(8) 0.8890(14) 0.116(6) Uani 1 1 d . . . H18A H 0.9138 -0.1004 0.8184 0.175 Uiso 1 1 calc R . . H18B H 0.9817 -0.1095 0.9323 0.175 Uiso 1 1 calc R . . H18C H 0.9256 -0.0229 0.8925 0.175 Uiso 1 1 calc R . . C19 C 0.8507(15) 0.1550(7) 0.8524(12) 0.080(4) Uani 1 1 d . . . C20 C 0.5474(16) 0.3126(9) 1.0014(13) 0.122(6) Uani 1 1 d . . . H20A H 0.4831 0.3426 1.0383 0.183 Uiso 1 1 calc R . . H20B H 0.6133 0.2868 1.0503 0.183 Uiso 1 1 calc R . . H20C H 0.5012 0.2705 0.9589 0.183 Uiso 1 1 calc R . . C21 C 0.6132(15) 0.3680(14) 0.9376(15) 0.117(6) Uani 1 1 d . . . 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 0.0507(2) 0.0452(2) 0.0760(3) 0.0009(2) 0.01499(18) 0.0029(2) S1 0.110(3) 0.141(4) 0.229(6) 0.095(4) 0.078(4) 0.018(3) O1 0.057(4) 0.050(4) 0.070(5) 0.003(4) 0.009(3) -0.008(3) O2 0.055(4) 0.050(4) 0.067(5) -0.003(3) 0.012(3) 0.006(3) O3 0.052(5) 0.040(5) 0.069(6) -0.004(4) 0.018(5) 0.004(4) N1 0.071(6) 0.061(6) 0.086(7) 0.020(5) 0.025(5) 0.013(5) N2 0.080(6) 0.039(5) 0.083(7) -0.002(5) 0.027(5) 0.003(4) N3 0.084(7) 0.049(6) 0.055(6) 0.008(5) 0.007(5) 0.031(5) N4 0.113(14) 0.28(3) 0.24(3) 0.08(2) 0.006(14) -0.060(16) C22 0.043(5) 0.065(7) 0.071(7) -0.001(6) 0.008(5) -0.021(5) C2 0.066(7) 0.070(8) 0.083(9) 0.006(7) 0.005(6) -0.010(6) C3 0.078(8) 0.092(10) 0.073(9) -0.018(7) 0.010(7) -0.029(7) C4 0.082(9) 0.103(12) 0.094(11) 0.024(9) -0.003(8) -0.028(8) C5 0.073(8) 0.100(11) 0.095(11) 0.039(9) -0.009(8) -0.033(8) C6 0.041(5) 0.063(7) 0.107(10) 0.026(7) 0.001(6) -0.009(5) C7 0.054(6) 0.062(8) 0.116(11) 0.020(8) 0.023(7) 0.017(5) C8 0.058(7) 0.040(6) 0.157(13) 0.011(7) 0.048(8) 0.012(5) C9 0.083(9) 0.089(10) 0.116(12) -0.023(9) 0.010(9) 0.016(8) C10 0.073(7) 0.047(6) 0.084(9) -0.017(6) 0.029(6) -0.010(5) C11 0.051(6) 0.052(6) 0.082(8) -0.009(5) 0.011(5) -0.020(5) C12 0.077(8) 0.067(7) 0.069(8) -0.015(6) 0.018(6) -0.021(6) C13 0.082(9) 0.090(10) 0.081(9) 0.006(8) -0.005(7) -0.019(8) C14 0.056(7) 0.099(10) 0.084(9) 0.002(8) -0.002(6) -0.011(7) C15 0.045(5) 0.058(6) 0.080(8) 0.006(6) 0.003(5) -0.008(5) C16 0.036(5) 0.049(6) 0.071(7) -0.002(5) 0.005(5) -0.010(4) C17 0.133(13) 0.048(7) 0.179(17) 0.000(9) 0.056(12) 0.002(8) C18 0.085(10) 0.066(8) 0.199(18) 0.055(10) 0.018(11) 0.007(7) C19 0.103(11) 0.027(6) 0.103(11) -0.001(6) -0.032(9) 0.036(6) C20 0.113(13) 0.090(11) 0.156(16) 0.042(11) -0.029(11) -0.031(9) C21 0.066(10) 0.151(18) 0.132(16) -0.019(13) -0.004(10) -0.024(10) _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 O3 1.8385(4) . ? Re1 O1 2.004(7) . ? Re1 O2 2.008(7) . ? Re1 N2 2.028(9) . ? Re1 N1 2.046(9) . ? Re1 N3 2.125(11) . ? S1 C19 1.687(18) . ? O1 C22 1.334(12) . ? O2 C16 1.335(12) . ? O3 Re1 1.8385(4) 3_657 ? N1 C7 1.273(16) . ? N1 C8 1.602(16) . ? N2 C10 1.301(14) . ? N2 C9 1.494(16) . ? N3 C19 0.973(16) . ? N4 C21 1.10(2) . ? C22 C2 1.391(16) . ? C22 C6 1.407(15) . ? C2 C3 1.386(17) . ? C2 H2 0.9500 . ? C3 C4 1.395(19) . ? C3 H3 0.9500 . ? C4 C5 1.37(2) . ? C4 H4 0.9500 . ? C5 C6 1.415(17) . ? C5 H5 0.9500 . ? C6 C7 1.442(17) . ? C7 H7 0.9500 . ? C8 C9 1.413(18) . ? C8 C18 1.421(16) . ? C8 C17 1.563(17) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.430(16) . ? C10 H10 0.9500 . ? C11 C16 1.411(14) . ? C11 C12 1.417(16) . ? C12 C13 1.358(17) . ? C12 H12 0.9500 . ? C13 C14 1.378(18) . ? C13 H13 0.9500 . ? C14 C15 1.362(16) . ? C14 H14 0.9500 . ? C15 C16 1.376(14) . ? C15 H15 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C20 C21 1.44(2) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? 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 O3 Re1 O1 90.98(18) . . ? O3 Re1 O2 92.12(19) . . ? O1 Re1 O2 98.6(3) . . ? O3 Re1 N2 92.9(3) . . ? O1 Re1 N2 170.9(3) . . ? O2 Re1 N2 89.4(3) . . ? O3 Re1 N1 87.6(3) . . ? O1 Re1 N1 91.2(4) . . ? O2 Re1 N1 170.2(4) . . ? N2 Re1 N1 80.8(4) . . ? O3 Re1 N3 178.3(3) . . ? O1 Re1 N3 87.4(3) . . ? O2 Re1 N3 87.7(3) . . ? N2 Re1 N3 88.7(4) . . ? N1 Re1 N3 92.9(4) . . ? C22 O1 Re1 124.2(7) . . ? C16 O2 Re1 125.9(6) . . ? Re1 O3 Re1 180.0 3_657 . ? C7 N1 C8 125.4(10) . . ? C7 N1 Re1 123.3(8) . . ? C8 N1 Re1 110.5(8) . . ? C10 N2 C9 121.0(10) . . ? C10 N2 Re1 125.3(7) . . ? C9 N2 Re1 113.6(8) . . ? C19 N3 Re1 163.7(13) . . ? O1 C22 C2 117.8(11) . . ? O1 C22 C6 124.0(11) . . ? C2 C22 C6 118.1(12) . . ? C3 C2 C22 122.4(12) . . ? C3 C2 H2 118.8 . . ? C22 C2 H2 118.8 . . ? C2 C3 C4 117.5(13) . . ? C2 C3 H3 121.2 . . ? C4 C3 H3 121.2 . . ? C5 C4 C3 123.2(14) . . ? C5 C4 H4 118.4 . . ? C3 C4 H4 118.4 . . ? C4 C5 C6 118.0(15) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? C22 C6 C5 120.8(14) . . ? C22 C6 C7 124.7(11) . . ? C5 C6 C7 114.6(12) . . ? N1 C7 C6 127.4(11) . . ? N1 C7 H7 116.3 . . ? C6 C7 H7 116.3 . . ? C9 C8 C18 117.5(14) . . ? C9 C8 C17 106.0(12) . . ? C18 C8 C17 109.2(10) . . ? C9 C8 N1 109.7(9) . . ? C18 C8 N1 106.1(11) . . ? C17 C8 N1 107.9(11) . . ? C8 C9 N2 107.3(11) . . ? C8 C9 H9A 110.3 . . ? N2 C9 H9A 110.3 . . ? C8 C9 H9B 110.3 . . ? N2 C9 H9B 110.3 . . ? H9A C9 H9B 108.5 . . ? N2 C10 C11 126.1(10) . . ? N2 C10 H10 116.9 . . ? C11 C10 H10 116.9 . . ? C16 C11 C12 119.1(11) . . ? C16 C11 C10 123.8(11) . . ? C12 C11 C10 117.1(11) . . ? C13 C12 C11 122.0(12) . . ? C13 C12 H12 119.0 . . ? C11 C12 H12 119.0 . . ? C12 C13 C14 117.3(13) . . ? C12 C13 H13 121.3 . . ? C14 C13 H13 121.3 . . ? C15 C14 C13 122.4(13) . . ? C15 C14 H14 118.8 . . ? C13 C14 H14 118.8 . . ? C14 C15 C16 121.8(12) . . ? C14 C15 H15 119.1 . . ? C16 C15 H15 119.1 . . ? O2 C16 C15 118.1(10) . . ? O2 C16 C11 124.5(9) . . ? C15 C16 C11 117.3(11) . . ? C8 C17 H17A 109.5 . . ? C8 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C8 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C8 C18 H18A 109.5 . . ? C8 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C8 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N3 C19 S1 174.5(13) . . ? C21 C20 H20A 109.5 . . ? C21 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C21 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N4 C21 C20 177(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 O3 Re1 O1 C22 62.5(7) . . . . ? O2 Re1 O1 C22 154.8(7) . . . . ? N2 Re1 O1 C22 -53(2) . . . . ? N1 Re1 O1 C22 -25.1(7) . . . . ? N3 Re1 O1 C22 -117.9(7) . . . . ? O3 Re1 O2 C16 -116.3(7) . . . . ? O1 Re1 O2 C16 152.4(7) . . . . ? N2 Re1 O2 C16 -23.4(7) . . . . ? N1 Re1 O2 C16 -28(2) . . . . ? N3 Re1 O2 C16 65.4(7) . . . . ? O1 Re1 O3 Re1 -45(5) . . . 3_657 ? O2 Re1 O3 Re1 -144(5) . . . 3_657 ? N2 Re1 O3 Re1 127(5) . . . 3_657 ? N1 Re1 O3 Re1 46(5) . . . 3_657 ? N3 Re1 O3 Re1 -61(10) . . . 3_657 ? O3 Re1 N1 C7 -74.1(10) . . . . ? O1 Re1 N1 C7 16.9(10) . . . . ? O2 Re1 N1 C7 -162.7(15) . . . . ? N2 Re1 N1 C7 -167.4(10) . . . . ? N3 Re1 N1 C7 104.4(10) . . . . ? O3 Re1 N1 C8 96.5(6) . . . . ? O1 Re1 N1 C8 -172.5(6) . . . . ? O2 Re1 N1 C8 8(2) . . . . ? N2 Re1 N1 C8 3.2(6) . . . . ? N3 Re1 N1 C8 -85.1(7) . . . . ? O3 Re1 N2 C10 112.9(9) . . . . ? O1 Re1 N2 C10 -131.5(18) . . . . ? O2 Re1 N2 C10 20.8(9) . . . . ? N1 Re1 N2 C10 -160.0(10) . . . . ? N3 Re1 N2 C10 -66.8(9) . . . . ? O3 Re1 N2 C9 -65.8(8) . . . . ? O1 Re1 N2 C9 50(2) . . . . ? O2 Re1 N2 C9 -157.9(8) . . . . ? N1 Re1 N2 C9 21.3(8) . . . . ? N3 Re1 N2 C9 114.4(8) . . . . ? O3 Re1 N3 C19 -114(9) . . . . ? O1 Re1 N3 C19 -129(4) . . . . ? O2 Re1 N3 C19 -30(4) . . . . ? N2 Re1 N3 C19 59(4) . . . . ? N1 Re1 N3 C19 140(4) . . . . ? Re1 O1 C22 C2 -160.5(7) . . . . ? Re1 O1 C22 C6 21.7(12) . . . . ? O1 C22 C2 C3 -178.2(10) . . . . ? C6 C22 C2 C3 -0.3(16) . . . . ? C22 C2 C3 C4 -0.6(17) . . . . ? C2 C3 C4 C5 1.1(19) . . . . ? C3 C4 C5 C6 -0.6(19) . . . . ? O1 C22 C6 C5 178.5(9) . . . . ? C2 C22 C6 C5 0.7(14) . . . . ? O1 C22 C6 C7 -1.8(15) . . . . ? C2 C22 C6 C7 -179.6(10) . . . . ? C4 C5 C6 C22 -0.3(16) . . . . ? C4 C5 C6 C7 180.0(11) . . . . ? C8 N1 C7 C6 -174.0(10) . . . . ? Re1 N1 C7 C6 -4.8(17) . . . . ? C22 C6 C7 N1 -7.4(19) . . . . ? C5 C6 C7 N1 172.3(12) . . . . ? C7 N1 C8 C9 142.2(13) . . . . ? Re1 N1 C8 C9 -28.2(12) . . . . ? C7 N1 C8 C18 -89.9(14) . . . . ? Re1 N1 C8 C18 99.7(10) . . . . ? C7 N1 C8 C17 27.1(16) . . . . ? Re1 N1 C8 C17 -143.3(9) . . . . ? C18 C8 C9 N2 -77.0(14) . . . . ? C17 C8 C9 N2 160.6(10) . . . . ? N1 C8 C9 N2 44.3(14) . . . . ? C10 N2 C9 C8 137.9(12) . . . . ? Re1 N2 C9 C8 -43.3(13) . . . . ? C9 N2 C10 C11 166.9(11) . . . . ? Re1 N2 C10 C11 -11.7(16) . . . . ? N2 C10 C11 C16 -4.2(17) . . . . ? N2 C10 C11 C12 177.2(10) . . . . ? C16 C11 C12 C13 -2.3(16) . . . . ? C10 C11 C12 C13 176.4(10) . . . . ? C11 C12 C13 C14 -1.1(18) . . . . ? C12 C13 C14 C15 2.6(18) . . . . ? C13 C14 C15 C16 -0.4(17) . . . . ? Re1 O2 C16 C15 -167.3(6) . . . . ? Re1 O2 C16 C11 16.8(12) . . . . ? C14 C15 C16 O2 -179.2(9) . . . . ? C14 C15 C16 C11 -3.0(14) . . . . ? C12 C11 C16 O2 -179.8(9) . . . . ? C10 C11 C16 O2 1.6(15) . . . . ? C12 C11 C16 C15 4.3(13) . . . . ? C10 C11 C16 C15 -174.3(9) . . . . ? Re1 N3 C19 S1 -105(16) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.359 _refine_diff_density_min -0.826 _refine_diff_density_rms 0.139 _database_code_depnum_ccdc_archive 'CCDC 933554'