# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_aude1bon _database_code_depnum_ccdc_archive 'CCDC 857938' #TrackingRef 'aude1bon.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H22 Cl N O3 P Re' _chemical_formula_sum 'C28 H22 Cl N O3 P Re' _chemical_formula_weight 673.09 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' Cl Cl 0.1484 0.1585 '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' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 10.6088(9) _cell_length_b 15.0400(13) _cell_length_c 16.0365(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2558.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3113 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 25.74 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.747 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 4.946 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4532 _exptl_absorpt_correction_T_max 0.7074 _exptl_absorpt_process_details 'Sheldrick,G.M.(2002).SADABS BrukerAXS Inc.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method none _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 17744 _diffrn_reflns_av_R_equivalents 0.0943 _diffrn_reflns_av_sigmaI/netI 0.0989 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 26.43 _reflns_number_total 5249 _reflns_number_gt 4552 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SAINT (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0000P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.009(10) _refine_ls_number_reflns 5249 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.0826 _refine_ls_wR_factor_gt 0.0792 _refine_ls_goodness_of_fit_ref 0.938 _refine_ls_restrained_S_all 0.938 _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 0.97452(3) 0.89210(2) 0.054442(19) 0.01220(8) Uani 1 1 d . . . P1 P 1.12929(19) 0.97027(14) 0.14279(13) 0.0120(4) Uani 1 1 d . . . N1 N 0.8548(6) 0.9405(4) 0.1584(4) 0.0121(14) Uani 1 1 d . . . C100 C 1.0847(8) 0.8547(5) -0.0330(5) 0.019(2) Uani 1 1 d . . . C200 C 0.8352(8) 0.8434(5) -0.0076(5) 0.0176(19) Uani 1 1 d . . . C300 C 0.9917(7) 0.7794(6) 0.1095(5) 0.022(2) Uani 1 1 d . . . Cl1 Cl 0.93905(18) 1.03993(13) -0.01003(12) 0.0189(5) Uani 1 1 d . . . O100 O 1.1505(6) 0.8295(5) -0.0857(4) 0.0395(18) Uani 1 1 d . . . O200 O 0.7538(5) 0.8156(4) -0.0477(4) 0.0326(15) Uani 1 1 d . . . O300 O 0.9988(5) 0.7135(4) 0.1418(4) 0.0277(16) Uani 1 1 d . . . C1 C 1.0176(8) 1.0467(5) 0.1868(4) 0.0159(17) Uani 1 1 d . . . C2 C 1.0507(7) 1.1304(5) 0.1655(5) 0.0147(18) Uani 1 1 d . . . C3 C 0.9655(8) 1.2083(5) 0.1611(5) 0.0193(17) Uani 1 1 d . . . H3A H 0.9108 1.2077 0.2095 0.023 Uiso 1 1 calc R . . H3B H 0.9126 1.2024 0.1120 0.023 Uiso 1 1 calc R . . C4 C 1.0335(8) 1.2986(5) 0.1573(5) 0.0250(19) Uani 1 1 d . . . H4A H 0.9738 1.3446 0.1419 0.030 Uiso 1 1 calc R . . H4B H 1.0670 1.3129 0.2120 0.030 Uiso 1 1 calc R . . C5 C 1.1416(8) 1.2964(6) 0.0935(6) 0.028(2) Uani 1 1 d . . . H5A H 1.1079 1.2835 0.0386 0.033 Uiso 1 1 calc R . . H5B H 1.1820 1.3542 0.0914 0.033 Uiso 1 1 calc R . . C6 C 1.2379(8) 1.2265(5) 0.1168(6) 0.025(2) Uani 1 1 d . . . H6A H 1.2997 1.2218 0.0725 0.029 Uiso 1 1 calc R . . H6B H 1.2816 1.2452 0.1670 0.029 Uiso 1 1 calc R . . C7 C 1.1808(7) 1.1375(5) 0.1314(5) 0.0162(19) Uani 1 1 d . . . C8 C 1.2357(7) 1.0593(5) 0.1134(5) 0.0138(18) Uani 1 1 d . . . C9 C 1.3630(7) 1.0418(5) 0.0832(5) 0.0134(18) Uani 1 1 d . . . C10 C 1.4660(8) 1.0890(5) 0.1135(4) 0.0162(17) Uani 1 1 d . . . H10 H 1.4547 1.1316 0.1548 0.019 Uiso 1 1 calc R . . C11 C 1.5849(8) 1.0727(6) 0.0825(5) 0.024(2) Uani 1 1 d . . . H11 H 1.6530 1.1049 0.1030 0.029 Uiso 1 1 calc R . . C12 C 1.6044(8) 1.0103(6) 0.0223(6) 0.023(2) Uani 1 1 d . . . H12 H 1.6849 1.0007 0.0012 0.028 Uiso 1 1 calc R . . C13 C 1.5046(8) 0.9619(6) -0.0069(5) 0.027(2) Uani 1 1 d . . . H13 H 1.5177 0.9190 -0.0478 0.032 Uiso 1 1 calc R . . C14 C 1.3858(8) 0.9758(6) 0.0234(5) 0.023(2) Uani 1 1 d . . . H14 H 1.3194 0.9411 0.0042 0.028 Uiso 1 1 calc R . . C15 C 0.8922(7) 1.0116(5) 0.2057(5) 0.0147(18) Uani 1 1 d . . . C16 C 0.8171(8) 1.0440(6) 0.2695(5) 0.021(2) Uani 1 1 d . . . H16 H 0.8428 1.0938 0.2993 0.025 Uiso 1 1 calc R . . C17 C 0.7046(8) 1.0032(6) 0.2893(6) 0.027(2) Uani 1 1 d . . . H17 H 0.6552 1.0237 0.3332 0.032 Uiso 1 1 calc R . . C18 C 0.6673(8) 0.9307(6) 0.2417(6) 0.022(2) Uani 1 1 d . . . H18 H 0.5919 0.9017 0.2533 0.027 Uiso 1 1 calc R . . C19 C 0.7435(7) 0.9021(6) 0.1769(5) 0.0157(17) Uani 1 1 d . . . H19 H 0.7166 0.8542 0.1448 0.019 Uiso 1 1 calc R . . C20 C 1.2171(7) 0.9128(5) 0.2237(5) 0.0130(18) Uani 1 1 d . . . C21 C 1.2717(7) 0.8309(6) 0.2066(6) 0.022(2) Uani 1 1 d . . . H21 H 1.2580 0.8042 0.1551 0.026 Uiso 1 1 calc R . . C22 C 1.3449(8) 0.7893(6) 0.2645(6) 0.028(2) Uani 1 1 d . . . H22 H 1.3818 0.7347 0.2522 0.033 Uiso 1 1 calc R . . C23 C 1.3643(8) 0.8281(6) 0.3410(6) 0.031(2) Uani 1 1 d . . . H23 H 1.4154 0.8002 0.3802 0.037 Uiso 1 1 calc R . . C24 C 1.3092(8) 0.9072(6) 0.3596(5) 0.030(2) Uani 1 1 d . . . H24 H 1.3204 0.9320 0.4122 0.036 Uiso 1 1 calc R . . C25 C 1.2360(8) 0.9512(6) 0.3007(6) 0.026(2) Uani 1 1 d . . . H25 H 1.2001 1.0060 0.3132 0.031 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 0.00932(13) 0.01517(15) 0.01211(14) -0.00229(15) -0.00029(13) -0.00116(14) P1 0.0091(10) 0.0128(11) 0.0140(11) -0.0021(9) -0.0002(8) 0.0017(9) N1 0.013(4) 0.016(4) 0.007(3) 0.001(3) -0.003(3) -0.001(3) C100 0.020(4) 0.013(4) 0.023(5) 0.001(3) -0.004(4) -0.003(4) C200 0.017(5) 0.012(5) 0.024(5) 0.004(4) 0.008(4) 0.006(4) C300 0.010(5) 0.045(6) 0.010(4) -0.018(4) -0.002(3) 0.003(4) Cl1 0.0187(11) 0.0236(11) 0.0145(10) 0.0021(9) -0.0011(8) -0.0027(8) O100 0.035(4) 0.051(5) 0.032(4) -0.013(4) 0.014(3) 0.010(4) O200 0.023(3) 0.031(4) 0.044(4) -0.014(4) -0.014(3) 0.003(3) O300 0.029(4) 0.026(3) 0.028(4) 0.008(3) 0.003(3) 0.000(3) C1 0.013(4) 0.021(4) 0.013(4) -0.002(3) -0.004(4) 0.002(4) C2 0.012(4) 0.013(4) 0.018(4) -0.011(3) -0.004(3) 0.002(3) C3 0.024(4) 0.016(4) 0.018(4) -0.007(3) 0.002(4) 0.004(4) C4 0.024(5) 0.021(5) 0.029(5) -0.006(4) 0.004(4) 0.006(4) C5 0.037(6) 0.018(5) 0.028(5) 0.005(4) 0.002(4) -0.002(4) C6 0.028(5) 0.013(5) 0.032(6) 0.004(4) 0.007(4) 0.000(4) C7 0.012(4) 0.023(5) 0.013(4) -0.003(4) 0.002(3) 0.005(4) C8 0.014(4) 0.019(5) 0.009(4) 0.003(4) -0.004(3) -0.008(4) C9 0.010(4) 0.016(4) 0.014(4) 0.003(3) 0.001(3) 0.002(3) C10 0.022(4) 0.013(4) 0.014(4) -0.003(3) 0.001(4) 0.004(4) C11 0.014(4) 0.024(5) 0.033(5) 0.009(4) -0.007(4) -0.001(4) C12 0.011(5) 0.023(5) 0.036(6) 0.008(4) 0.008(4) 0.001(4) C13 0.025(6) 0.022(5) 0.035(5) -0.006(4) 0.005(4) -0.002(4) C14 0.011(5) 0.026(5) 0.033(5) -0.008(4) 0.002(4) -0.003(4) C15 0.011(4) 0.023(5) 0.010(4) 0.001(4) -0.002(3) -0.001(4) C16 0.024(5) 0.022(5) 0.018(5) -0.004(4) -0.001(4) 0.001(4) C17 0.019(5) 0.040(6) 0.022(5) 0.005(4) 0.015(4) 0.000(5) C18 0.020(5) 0.018(5) 0.029(6) 0.014(4) 0.001(4) -0.007(4) C19 0.013(4) 0.014(4) 0.020(4) 0.006(4) -0.003(3) -0.001(4) C20 0.005(4) 0.016(5) 0.019(4) 0.005(3) -0.001(3) -0.002(3) C21 0.017(4) 0.016(5) 0.032(5) -0.008(4) 0.001(4) 0.001(4) C22 0.021(5) 0.025(6) 0.037(6) 0.008(5) -0.011(4) -0.008(4) C23 0.019(5) 0.040(6) 0.034(6) 0.014(5) -0.009(4) -0.009(5) C24 0.030(5) 0.043(7) 0.017(5) 0.000(4) -0.008(4) -0.004(5) C25 0.021(5) 0.029(6) 0.027(5) -0.004(4) -0.009(4) 0.008(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 C100 1.910(9) . ? Re1 C300 1.921(10) . ? Re1 C200 1.926(9) . ? Re1 N1 2.218(6) . ? Re1 P1 2.467(2) . ? Re1 Cl1 2.481(2) . ? P1 C1 1.796(8) . ? P1 C8 1.814(8) . ? P1 C20 1.816(8) . ? N1 C19 1.348(9) . ? N1 C15 1.369(10) . ? C100 O100 1.160(9) . ? C200 O200 1.155(9) . ? C300 O300 1.119(9) . ? C1 C2 1.351(10) . ? C1 C15 1.463(11) . ? C2 C3 1.481(10) . ? C2 C7 1.489(10) . ? C3 C4 1.539(10) . ? C4 C5 1.537(12) . ? C5 C6 1.513(11) . ? C6 C7 1.487(11) . ? C7 C8 1.345(11) . ? C8 C9 1.458(10) . ? C9 C10 1.391(11) . ? C9 C14 1.401(11) . ? C10 C11 1.378(11) . ? C11 C12 1.363(11) . ? C12 C13 1.367(11) . ? C13 C14 1.367(11) . ? C15 C16 1.386(11) . ? C16 C17 1.378(11) . ? C17 C18 1.389(12) . ? C18 C19 1.385(11) . ? C20 C25 1.377(11) . ? C20 C21 1.388(11) . ? C21 C22 1.363(12) . ? C22 C23 1.375(13) . ? C23 C24 1.358(12) . ? C24 C25 1.390(12) . ? 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 C100 Re1 C300 91.1(3) . . ? C100 Re1 C200 88.8(3) . . ? C300 Re1 C200 88.6(3) . . ? C100 Re1 N1 176.9(3) . . ? C300 Re1 N1 89.9(3) . . ? C200 Re1 N1 94.2(3) . . ? C100 Re1 P1 98.9(2) . . ? C300 Re1 P1 95.3(2) . . ? C200 Re1 P1 171.3(2) . . ? N1 Re1 P1 78.06(16) . . ? C100 Re1 Cl1 92.9(2) . . ? C300 Re1 Cl1 175.8(2) . . ? C200 Re1 Cl1 90.5(2) . . ? N1 Re1 Cl1 86.11(16) . . ? P1 Re1 Cl1 85.02(7) . . ? C1 P1 C8 92.3(4) . . ? C1 P1 C20 111.2(4) . . ? C8 P1 C20 102.6(3) . . ? C1 P1 Re1 95.3(3) . . ? C8 P1 Re1 128.1(3) . . ? C20 P1 Re1 121.7(3) . . ? C19 N1 C15 117.8(7) . . ? C19 N1 Re1 121.8(5) . . ? C15 N1 Re1 120.4(5) . . ? O100 C100 Re1 178.0(8) . . ? O200 C200 Re1 177.2(8) . . ? O300 C300 Re1 178.4(7) . . ? C2 C1 C15 128.7(7) . . ? C2 C1 P1 109.0(6) . . ? C15 C1 P1 116.7(6) . . ? C1 C2 C3 126.2(7) . . ? C1 C2 C7 113.6(7) . . ? C3 C2 C7 119.4(7) . . ? C2 C3 C4 114.4(7) . . ? C5 C4 C3 110.9(6) . . ? C6 C5 C4 110.7(7) . . ? C7 C6 C5 112.9(7) . . ? C8 C7 C6 125.3(7) . . ? C8 C7 C2 114.7(7) . . ? C6 C7 C2 120.0(7) . . ? C7 C8 C9 129.1(7) . . ? C7 C8 P1 108.7(6) . . ? C9 C8 P1 122.0(6) . . ? C10 C9 C14 117.7(7) . . ? C10 C9 C8 121.3(7) . . ? C14 C9 C8 121.0(7) . . ? C11 C10 C9 120.1(7) . . ? C12 C11 C10 121.2(8) . . ? C11 C12 C13 119.4(8) . . ? C12 C13 C14 120.7(8) . . ? C13 C14 C9 120.8(8) . . ? N1 C15 C16 121.1(7) . . ? N1 C15 C1 115.5(7) . . ? C16 C15 C1 123.3(7) . . ? C17 C16 C15 120.8(8) . . ? C16 C17 C18 118.0(8) . . ? C19 C18 C17 119.4(8) . . ? N1 C19 C18 122.9(8) . . ? C25 C20 C21 119.2(8) . . ? C25 C20 P1 121.1(6) . . ? C21 C20 P1 119.6(6) . . ? C22 C21 C20 120.7(9) . . ? C21 C22 C23 119.8(9) . . ? C24 C23 C22 120.3(9) . . ? C23 C24 C25 120.5(9) . . ? C20 C25 C24 119.4(9) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.43 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.792 _refine_diff_density_min -1.286 _refine_diff_density_rms 0.177 data_audeboutbon _database_code_depnum_ccdc_archive 'CCDC 857939' #TrackingRef 'audeboutbon.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H24 Cl3 N O3 P Re' _chemical_formula_sum 'C29 H24 Cl3 N O3 P Re' _chemical_formula_weight 758.01 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' Cl Cl 0.1484 0.1585 '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' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M p212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 11.2329(8) _cell_length_b 14.0307(12) _cell_length_c 17.9380(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2827.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9420 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 26.28 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.781 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 4.670 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3930 _exptl_absorpt_correction_T_max 0.6568 _exptl_absorpt_process_details 'Sheldrick,G.M.(2002).SADABS BrukerAXS Inc.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ccd _diffrn_measurement_method none _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 21631 _diffrn_reflns_av_R_equivalents 0.0529 _diffrn_reflns_av_sigmaI/netI 0.0532 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 26.35 _reflns_number_total 5754 _reflns_number_gt 5490 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SAINT (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0387P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.003(8) _refine_ls_number_reflns 5754 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0270 _refine_ls_R_factor_gt 0.0241 _refine_ls_wR_factor_ref 0.0814 _refine_ls_wR_factor_gt 0.0581 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _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 0.63099(2) 0.216004(15) 0.102781(12) 0.01436(7) Uani 1 1 d . . . Cl1 Cl 0.64871(16) 0.31108(11) 0.21872(9) 0.0284(4) Uani 1 1 d . . . N1 N 0.4392(4) 0.2114(4) 0.1357(3) 0.0174(10) Uani 1 1 d . . . P1 P 0.62407(15) 0.06926(10) 0.17681(8) 0.0128(3) Uani 1 1 d . . . C200 C 0.7986(6) 0.2197(5) 0.0831(4) 0.0256(14) Uani 1 1 d . . . C300 C 0.6141(6) 0.3298(4) 0.0409(3) 0.0204(13) Uani 1 1 d . . . C400 C 0.6000(5) 0.1357(5) 0.0170(4) 0.0212(14) Uani 1 1 d . . . O200 O 0.8999(4) 0.2231(4) 0.0712(3) 0.0403(13) Uani 1 1 d . . . O300 O 0.6092(5) 0.3951(3) 0.0028(3) 0.0341(12) Uani 1 1 d . . . O400 O 0.5766(4) 0.0886(4) -0.0307(3) 0.0319(12) Uani 1 1 d . . . C1 C 0.4682(5) 0.0453(4) 0.1609(3) 0.0169(13) Uani 1 1 d . . . C2 C 0.4557(5) -0.0430(4) 0.1310(4) 0.0181(13) Uani 1 1 d . . . C3 C 0.3396(5) -0.0790(4) 0.0978(4) 0.0227(13) Uani 1 1 d . . . H3A H 0.3184 -0.0389 0.0558 0.027 Uiso 1 1 calc R . . H3B H 0.2772 -0.0729 0.1348 0.027 Uiso 1 1 calc R . . C4 C 0.3451(6) -0.1824(4) 0.0717(4) 0.0234(14) Uani 1 1 d . . . H4A H 0.2800 -0.1947 0.0375 0.028 Uiso 1 1 calc R . . H4B H 0.3358 -0.2244 0.1143 0.028 Uiso 1 1 calc R . . C5 C 0.4635(6) -0.2040(5) 0.0329(4) 0.0258(15) Uani 1 1 d . . . H5A H 0.4620 -0.2679 0.0122 0.031 Uiso 1 1 calc R . . H5B H 0.4763 -0.1592 -0.0075 0.031 Uiso 1 1 calc R . . C6 C 0.5637(5) -0.1954(4) 0.0901(4) 0.0221(14) Uani 1 1 d . . . H6A H 0.5524 -0.2427 0.1288 0.026 Uiso 1 1 calc R . . H6B H 0.6393 -0.2082 0.0659 0.026 Uiso 1 1 calc R . . C7 C 0.5672(5) -0.0969(4) 0.1249(3) 0.0159(13) Uani 1 1 d . . . C8 C 0.6671(5) -0.0490(4) 0.1459(3) 0.0165(13) Uani 1 1 d . . . C9 C 0.7911(5) -0.0846(4) 0.1459(3) 0.0165(13) Uani 1 1 d . . . C10 C 0.8169(6) -0.1777(5) 0.1682(4) 0.0212(14) Uani 1 1 d . . . H10 H 0.7557 -0.2172 0.1846 0.025 Uiso 1 1 calc R . . C11 C 0.9333(5) -0.2121(5) 0.1663(4) 0.0240(14) Uani 1 1 d . . . H11 H 0.9495 -0.2742 0.1812 0.029 Uiso 1 1 calc R . . C12 C 1.0237(6) -0.1543(5) 0.1423(4) 0.0240(14) Uani 1 1 d . . . H12 H 1.1014 -0.1772 0.1412 0.029 Uiso 1 1 calc R . . C13 C 1.0002(5) -0.0617(4) 0.1197(4) 0.0210(14) Uani 1 1 d . . . H13 H 1.0616 -0.0229 0.1029 0.025 Uiso 1 1 calc R . . C14 C 0.8853(6) -0.0273(4) 0.1224(3) 0.0205(13) Uani 1 1 d . . . H14 H 0.8703 0.0353 0.1082 0.025 Uiso 1 1 calc R . . C15 C 0.3880(5) 0.1274(4) 0.1573(3) 0.0168(12) Uani 1 1 d . . . C16 C 0.2662(6) 0.1232(5) 0.1736(4) 0.0234(15) Uani 1 1 d . . . H16 H 0.2323 0.0660 0.1890 0.028 Uiso 1 1 calc R . . C17 C 0.1962(6) 0.2038(6) 0.1671(4) 0.0318(17) Uani 1 1 d . . . H17 H 0.1147 0.2009 0.1761 0.038 Uiso 1 1 calc R . . C18 C 0.2496(6) 0.2893(6) 0.1467(4) 0.0322(16) Uani 1 1 d . . . H18 H 0.2046 0.3448 0.1431 0.039 Uiso 1 1 calc R . . C19 C 0.3711(6) 0.2909(5) 0.1318(3) 0.0276(14) Uani 1 1 d . . . H19 H 0.4067 0.3484 0.1188 0.033 Uiso 1 1 calc R . . C20 C 0.6561(5) 0.0704(4) 0.2757(3) 0.0142(12) Uani 1 1 d . . . C21 C 0.5685(6) 0.0464(4) 0.3285(4) 0.0217(14) Uani 1 1 d . . . H21 H 0.4922 0.0300 0.3130 0.026 Uiso 1 1 calc R . . C22 C 0.5966(6) 0.0474(5) 0.4034(4) 0.0287(16) Uani 1 1 d . . . H22 H 0.5386 0.0327 0.4386 0.034 Uiso 1 1 calc R . . C23 C 0.7105(6) 0.0701(5) 0.4264(4) 0.0252(15) Uani 1 1 d . . . H23 H 0.7291 0.0697 0.4769 0.030 Uiso 1 1 calc R . . C24 C 0.7971(6) 0.0935(5) 0.3747(4) 0.0278(16) Uani 1 1 d . . . H24 H 0.8738 0.1086 0.3904 0.033 Uiso 1 1 calc R . . C25 C 0.7694(5) 0.0944(5) 0.3000(4) 0.0228(14) Uani 1 1 d . . . H25 H 0.8273 0.1113 0.2654 0.027 Uiso 1 1 calc R . . C900 C 0.8341(7) 0.4744(6) 0.1279(5) 0.0371(19) Uani 1 1 d . . . H90A H 0.7812 0.4224 0.1409 0.044 Uiso 1 1 calc R . . H90B H 0.8748 0.4574 0.0822 0.044 Uiso 1 1 calc R . . Cl10 Cl 0.74871(18) 0.57799(13) 0.11229(12) 0.0412(5) Uani 1 1 d . . . Cl20 Cl 0.93848(18) 0.48848(18) 0.19832(12) 0.0494(5) 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 0.01804(12) 0.01283(10) 0.01221(11) 0.00076(9) 0.00025(10) 0.00045(10) Cl1 0.0421(10) 0.0226(7) 0.0205(8) -0.0036(6) -0.0015(7) -0.0007(7) N1 0.021(2) 0.022(2) 0.010(2) 0.000(2) -0.0002(19) 0.006(2) P1 0.0131(7) 0.0134(6) 0.0119(7) -0.0002(5) -0.0014(6) -0.0005(6) C200 0.037(4) 0.013(3) 0.027(4) 0.002(3) 0.000(3) -0.002(3) C300 0.023(3) 0.023(3) 0.014(3) -0.005(2) 0.002(3) 0.003(3) C400 0.017(3) 0.026(3) 0.021(3) 0.013(3) 0.006(3) 0.007(3) O200 0.019(2) 0.039(3) 0.063(4) 0.008(3) 0.014(2) -0.004(2) O300 0.050(3) 0.022(2) 0.030(3) 0.012(2) -0.003(3) 0.003(2) O400 0.041(3) 0.028(3) 0.027(3) -0.007(2) 0.000(2) 0.000(2) C1 0.015(3) 0.022(3) 0.014(3) 0.002(3) 0.000(2) -0.003(3) C2 0.016(3) 0.018(3) 0.020(3) 0.005(3) 0.000(2) -0.005(2) C3 0.017(3) 0.026(3) 0.025(4) -0.002(3) -0.005(3) -0.005(2) C4 0.024(4) 0.026(3) 0.020(3) -0.001(3) -0.003(3) -0.012(3) C5 0.036(4) 0.020(3) 0.022(3) -0.008(3) 0.001(3) -0.007(3) C6 0.021(3) 0.018(3) 0.027(4) -0.006(3) 0.003(3) -0.002(2) C7 0.020(3) 0.017(3) 0.011(3) 0.001(2) 0.000(2) -0.003(2) C8 0.019(3) 0.014(3) 0.017(3) -0.002(2) 0.001(2) 0.000(2) C9 0.016(3) 0.017(3) 0.016(3) -0.003(3) -0.001(2) 0.000(2) C10 0.022(3) 0.020(3) 0.022(4) 0.003(3) 0.001(3) -0.001(3) C11 0.024(3) 0.020(3) 0.028(4) 0.004(3) 0.006(3) 0.005(3) C12 0.020(3) 0.029(4) 0.023(4) -0.001(3) 0.002(3) 0.006(3) C13 0.016(3) 0.019(3) 0.028(4) 0.004(3) 0.004(3) -0.003(2) C14 0.020(3) 0.019(3) 0.023(3) 0.002(2) 0.001(3) -0.002(3) C15 0.016(3) 0.025(3) 0.009(3) -0.004(2) -0.002(2) -0.001(3) C16 0.020(3) 0.031(4) 0.019(4) -0.007(3) -0.001(3) 0.000(3) C17 0.018(3) 0.054(5) 0.024(4) -0.010(4) -0.002(3) 0.009(4) C18 0.030(4) 0.042(4) 0.025(4) -0.002(4) -0.001(3) 0.020(4) C19 0.035(4) 0.024(3) 0.023(3) 0.000(3) 0.002(3) 0.015(4) C20 0.017(3) 0.010(3) 0.015(3) 0.004(2) 0.000(2) 0.002(2) C21 0.024(3) 0.018(3) 0.023(4) 0.003(3) -0.001(3) -0.006(3) C22 0.042(4) 0.023(3) 0.021(4) 0.000(3) 0.012(3) -0.006(3) C23 0.042(4) 0.022(3) 0.011(3) -0.001(3) -0.006(3) 0.008(3) C24 0.024(4) 0.039(4) 0.020(4) -0.001(3) -0.010(3) 0.004(3) C25 0.016(3) 0.035(4) 0.017(3) -0.001(3) -0.001(3) -0.002(3) C900 0.035(4) 0.037(4) 0.039(5) -0.003(3) -0.002(3) 0.003(3) Cl10 0.0455(11) 0.0335(9) 0.0447(12) 0.0006(9) 0.0007(9) 0.0029(8) Cl20 0.0358(10) 0.0745(15) 0.0380(12) -0.0035(11) -0.0048(9) 0.0033(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 C200 1.916(7) . ? Re1 C400 1.939(7) . ? Re1 C300 1.954(6) . ? Re1 N1 2.235(5) . ? Re1 P1 2.4513(14) . ? Re1 Cl1 2.4788(16) . ? N1 C19 1.354(8) . ? N1 C15 1.368(8) . ? P1 C1 1.806(6) . ? P1 C20 1.811(6) . ? P1 C8 1.815(6) . ? C200 O200 1.158(8) . ? C300 O300 1.144(7) . ? C400 O400 1.113(8) . ? C1 C2 1.357(9) . ? C1 C15 1.463(8) . ? C2 C7 1.468(8) . ? C2 C3 1.520(8) . ? C3 C4 1.526(9) . ? C4 C5 1.531(9) . ? C5 C6 1.528(9) . ? C6 C7 1.517(8) . ? C7 C8 1.361(8) . ? C8 C9 1.480(8) . ? C9 C14 1.394(8) . ? C9 C10 1.397(9) . ? C10 C11 1.394(9) . ? C11 C12 1.370(9) . ? C12 C13 1.387(9) . ? C13 C14 1.378(8) . ? C15 C16 1.400(9) . ? C16 C17 1.383(9) . ? C17 C18 1.390(11) . ? C18 C19 1.391(9) . ? C20 C25 1.387(8) . ? C20 C21 1.406(8) . ? C21 C22 1.380(9) . ? C22 C23 1.381(9) . ? C23 C24 1.384(10) . ? C24 C25 1.375(9) . ? C900 Cl20 1.734(8) . ? C900 Cl10 1.763(8) . ? 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 C200 Re1 C400 92.7(3) . . ? C200 Re1 C300 88.2(3) . . ? C400 Re1 C300 90.3(3) . . ? C200 Re1 N1 175.3(2) . . ? C400 Re1 N1 91.1(2) . . ? C300 Re1 N1 94.6(2) . . ? C200 Re1 P1 98.8(2) . . ? C400 Re1 P1 86.36(18) . . ? C300 Re1 P1 172.35(19) . . ? N1 Re1 P1 78.59(14) . . ? C200 Re1 Cl1 93.5(2) . . ? C400 Re1 Cl1 173.28(18) . . ? C300 Re1 Cl1 92.59(17) . . ? N1 Re1 Cl1 82.60(14) . . ? P1 Re1 Cl1 90.00(5) . . ? C19 N1 C15 119.1(5) . . ? C19 N1 Re1 120.5(5) . . ? C15 N1 Re1 120.3(4) . . ? C1 P1 C20 110.4(3) . . ? C1 P1 C8 92.3(3) . . ? C20 P1 C8 104.8(3) . . ? C1 P1 Re1 95.8(2) . . ? C20 P1 Re1 121.13(18) . . ? C8 P1 Re1 126.4(2) . . ? O200 C200 Re1 179.2(7) . . ? O300 C300 Re1 176.7(6) . . ? O400 C400 Re1 176.4(6) . . ? C2 C1 C15 129.6(6) . . ? C2 C1 P1 109.4(5) . . ? C15 C1 P1 117.2(4) . . ? C1 C2 C7 114.3(5) . . ? C1 C2 C3 123.2(6) . . ? C7 C2 C3 122.1(5) . . ? C2 C3 C4 113.7(5) . . ? C3 C4 C5 111.2(5) . . ? C6 C5 C4 108.6(5) . . ? C7 C6 C5 111.5(5) . . ? C8 C7 C2 115.3(5) . . ? C8 C7 C6 125.8(5) . . ? C2 C7 C6 118.6(5) . . ? C7 C8 C9 127.6(5) . . ? C7 C8 P1 108.5(4) . . ? C9 C8 P1 124.0(4) . . ? C14 C9 C10 118.0(6) . . ? C14 C9 C8 121.3(6) . . ? C10 C9 C8 120.7(6) . . ? C11 C10 C9 120.7(6) . . ? C12 C11 C10 119.9(6) . . ? C11 C12 C13 120.3(6) . . ? C14 C13 C12 119.8(6) . . ? C13 C14 C9 121.3(6) . . ? N1 C15 C16 120.4(6) . . ? N1 C15 C1 115.6(5) . . ? C16 C15 C1 124.0(6) . . ? C17 C16 C15 120.3(6) . . ? C16 C17 C18 118.9(6) . . ? C17 C18 C19 119.2(7) . . ? N1 C19 C18 122.1(7) . . ? C25 C20 C21 119.3(6) . . ? C25 C20 P1 119.5(5) . . ? C21 C20 P1 121.2(5) . . ? C22 C21 C20 119.5(6) . . ? C21 C22 C23 120.3(6) . . ? C22 C23 C24 120.4(6) . . ? C25 C24 C23 119.7(6) . . ? C24 C25 C20 120.8(6) . . ? Cl20 C900 Cl10 113.0(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.35 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.616 _refine_diff_density_min -1.288 _refine_diff_density_rms 0.257