# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_ren218 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H26 Cl2 N2 O2 P Re, C2H3N1' _chemical_formula_sum 'C33 H29 Cl2 N3 O2 P Re' _chemical_formula_weight 787.66 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' 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 orthorhombic _symmetry_space_group_name_H-M Pna21 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' _cell_length_a 22.0403(7) _cell_length_b 9.7351(3) _cell_length_c 14.5013(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3111.46(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 12301 _cell_measurement_theta_min 3.4672 _cell_measurement_theta_max 29.2375 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.174 _exptl_crystal_size_mid 0.109 _exptl_crystal_size_min 0.062 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.681 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 4.164 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details ;CrysAlis RED, (2005) ; _exptl_absorpt_correction_T_min 0.48531 _exptl_absorpt_correction_T_max 1.00000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20909 _diffrn_reflns_av_R_equivalents 0.0570 _diffrn_reflns_av_unetI/netI 0.0417 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5134 _reflns_number_gt 4576 _reflns_threshold_expression >2sigma(I) #========================================================================== # # REFINEMENT DATA _computing_data_collection 'CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000)' _computing_cell_refinement 'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)' _computing_data_reduction 'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;XP in SHELXTL/PC (Sheldrick, 1990b) ORTEP-3 W v. 1.062 (Farrugia 1997) ; _computing_publication_material ;SHELXL-97 (Sheldrick, 1997) and PLATON (Spek, 1990) ; _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^)+(0.0696P)^2^+0.2247P] 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 5134 _refine_ls_number_parameters 381 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1074 _refine_ls_wR_factor_gt 0.1035 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 0.087822(11) 0.81181(2) 0.38919(5) 0.02999(12) Uani 1 1 d . . . N1 N 0.0269(3) 0.7348(9) 0.2850(5) 0.0328(18) Uani 1 1 d . . . N2 N 0.0529(3) 0.9630(6) 0.4168(4) 0.0304(17) Uani 1 1 d . . . O1 O 0.1186(3) 0.6189(6) 0.3619(4) 0.0483(18) Uani 1 1 d . . . O2 O 0.1008(4) 0.4185(7) 0.2946(6) 0.072(2) Uani 1 1 d . . . P1 P 0.17232(10) 0.8339(2) 0.49619(17) 0.0328(5) Uani 1 1 d . . . Cl1 Cl 0.15408(11) 0.8843(3) 0.26821(16) 0.0446(5) Uani 1 1 d . . . Cl2 Cl 0.02299(15) 0.6862(2) 0.4942(2) 0.0501(7) Uani 1 1 d . . . C1 C 0.1914(4) 1.0133(8) 0.5235(6) 0.038(2) Uani 1 1 d . . . C2 C 0.1827(4) 1.1151(9) 0.4592(7) 0.048(2) Uani 1 1 d . . . H2 H 0.1669 1.0936 0.4015 0.058 Uiso 1 1 calc R . . C3 C 0.1975(6) 1.2510(11) 0.4804(10) 0.070(3) Uani 1 1 d . . . H3 H 0.1909 1.3208 0.4378 0.084 Uiso 1 1 calc R . . C4 C 0.2215(6) 1.2791(13) 0.5641(12) 0.075(4) Uani 1 1 d . . . H4 H 0.2313 1.3695 0.5786 0.091 Uiso 1 1 calc R . . C5 C 0.2317(6) 1.1810(11) 0.6267(9) 0.065(3) Uani 1 1 d . . . H5 H 0.2487 1.2035 0.6835 0.078 Uiso 1 1 calc R . . C6 C 0.2168(4) 1.0458(11) 0.6071(7) 0.053(2) Uani 1 1 d . . . H6 H 0.2240 0.9773 0.6504 0.063 Uiso 1 1 calc R . . C7 C 0.1631(3) 0.7574(8) 0.6097(6) 0.0344(19) Uani 1 1 d . . . C8 C 0.1142(5) 0.7982(9) 0.6628(8) 0.045(2) Uani 1 1 d . . . H8 H 0.0850 0.8563 0.6381 0.054 Uiso 1 1 calc R . . C9 C 0.1089(5) 0.7532(14) 0.7518(7) 0.059(3) Uani 1 1 d . . . H9 H 0.0760 0.7808 0.7872 0.071 Uiso 1 1 calc R . . C10 C 0.1515(6) 0.6683(12) 0.7889(9) 0.068(3) Uani 1 1 d . . . H10 H 0.1480 0.6398 0.8499 0.082 Uiso 1 1 calc R . . C11 C 0.1995(6) 0.6247(15) 0.7364(8) 0.076(4) Uani 1 1 d . . . H11 H 0.2277 0.5638 0.7612 0.091 Uiso 1 1 calc R . . C12 C 0.2064(5) 0.6705(10) 0.6472(8) 0.049(3) Uani 1 1 d . . . H12 H 0.2398 0.6435 0.6124 0.059 Uiso 1 1 calc R . . C13 C 0.2418(4) 0.7589(10) 0.4500(6) 0.040(2) Uani 1 1 d . . . C14 C 0.2917(4) 0.8389(10) 0.4272(7) 0.047(2) Uani 1 1 d . . . H14 H 0.2907 0.9334 0.4366 0.057 Uiso 1 1 calc R . . C15 C 0.3423(4) 0.7782(11) 0.3909(16) 0.067(3) Uani 1 1 d . . . H15 H 0.3762 0.8319 0.3784 0.081 Uiso 1 1 calc R . . C16 C 0.3443(4) 0.6416(12) 0.3726(10) 0.065(4) Uani 1 1 d . . . H16 H 0.3787 0.6032 0.3457 0.078 Uiso 1 1 calc R . . C17 C 0.2948(4) 0.5594(10) 0.3942(12) 0.061(2) Uani 1 1 d . . . H17 H 0.2961 0.4651 0.3839 0.074 Uiso 1 1 calc R . . C18 C 0.2441(4) 0.6196(11) 0.4310(7) 0.054(3) Uani 1 1 d . . . H18 H 0.2104 0.5655 0.4436 0.065 Uiso 1 1 calc R . . C19 C 0.0874(4) 0.5371(9) 0.3089(6) 0.043(2) Uani 1 1 d . . . C20 C 0.0340(4) 0.6025(10) 0.2653(7) 0.042(2) Uani 1 1 d . . . C21 C -0.0060(5) 0.5350(12) 0.2073(7) 0.058(3) Uani 1 1 d . . . H21 H -0.0011 0.4417 0.1958 0.070 Uiso 1 1 calc R . . C22 C -0.0518(5) 0.6047(12) 0.1677(8) 0.062(3) Uani 1 1 d . . . H22 H -0.0791 0.5598 0.1291 0.074 Uiso 1 1 calc R . . C23 C -0.0580(4) 0.7436(14) 0.1849(8) 0.058(3) Uani 1 1 d . . . H23 H -0.0891 0.7932 0.1573 0.070 Uiso 1 1 calc R . . C24 C -0.0173(4) 0.8089(10) 0.2436(7) 0.045(2) Uani 1 1 d . . . H24 H -0.0204 0.9028 0.2543 0.055 Uiso 1 1 calc R . . C25 C 0.0151(4) 1.0682(9) 0.4473(6) 0.0354(18) Uani 1 1 d . . . C26 C 0.0269(4) 1.2052(8) 0.4276(7) 0.039(2) Uani 1 1 d . . . H26 H 0.0607 1.2301 0.3930 0.047 Uiso 1 1 calc R . . C27 C -0.0128(5) 1.3041(9) 0.4606(8) 0.049(3) Uani 1 1 d . . . H27 H -0.0044 1.3962 0.4493 0.058 Uiso 1 1 calc R . . C28 C -0.0636(5) 1.2713(11) 0.5088(7) 0.046(2) Uani 1 1 d . . . C29 C -0.0746(5) 1.1356(13) 0.5283(8) 0.057(3) Uani 1 1 d . . . H29 H -0.1083 1.1122 0.5636 0.069 Uiso 1 1 calc R . . C30 C -0.0368(4) 1.0332(9) 0.4964(8) 0.052(3) Uani 1 1 d . . . H30 H -0.0459 0.9414 0.5076 0.062 Uiso 1 1 calc R . . C31 C -0.1059(5) 1.3826(13) 0.5440(8) 0.063(3) Uani 1 1 d . . . H31A H -0.0885 1.4712 0.5316 0.095 Uiso 1 1 calc R . . H31B H -0.1115 1.3719 0.6092 0.095 Uiso 1 1 calc R . . H31C H -0.1444 1.3752 0.5133 0.095 Uiso 1 1 calc R . . N99 N 0.0290(5) 0.1238(11) 0.2117(8) 0.075(3) Uani 1 1 d . . . C98 C 0.0716(7) 0.1637(12) 0.1823(9) 0.057(3) Uani 1 1 d . . . C99 C 0.1271(8) 0.2106(15) 0.1448(12) 0.095(5) Uani 1 1 d . . . H99A H 0.1375 0.2973 0.1721 0.143 Uiso 1 1 calc R . . H99B H 0.1229 0.2214 0.0793 0.143 Uiso 1 1 calc R . . H99C H 0.1584 0.1449 0.1576 0.143 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 0.02970(17) 0.02577(17) 0.03448(19) -0.0019(2) 0.0005(2) -0.00152(10) N1 0.020(3) 0.046(5) 0.032(4) -0.006(4) 0.005(3) 0.001(3) N2 0.027(3) 0.031(3) 0.033(5) -0.001(3) 0.002(2) -0.002(3) O1 0.044(3) 0.037(3) 0.065(5) -0.008(3) -0.005(3) 0.005(3) O2 0.096(6) 0.035(4) 0.084(6) -0.014(4) 0.003(5) 0.001(4) P1 0.0312(11) 0.0312(12) 0.0359(13) 0.0023(10) -0.0004(10) -0.0024(9) Cl1 0.0383(11) 0.0534(14) 0.0421(13) -0.0002(11) 0.0072(10) -0.0007(10) Cl2 0.0582(16) 0.0425(17) 0.0497(17) 0.0036(11) 0.0069(14) -0.0144(10) C1 0.038(5) 0.031(4) 0.047(5) -0.009(4) 0.003(4) -0.005(3) C2 0.055(6) 0.035(5) 0.054(6) 0.009(4) -0.007(5) -0.007(4) C3 0.083(8) 0.034(6) 0.093(10) 0.008(6) -0.017(7) -0.018(5) C4 0.073(8) 0.048(7) 0.106(12) -0.019(8) 0.008(8) -0.019(6) C5 0.069(8) 0.066(8) 0.059(8) -0.019(6) 0.004(6) -0.024(6) C6 0.049(6) 0.058(6) 0.051(6) -0.012(5) -0.002(5) -0.011(5) C7 0.034(5) 0.036(5) 0.033(5) 0.005(4) 0.003(4) -0.001(4) C8 0.035(5) 0.048(6) 0.052(7) 0.005(4) 0.006(5) 0.008(4) C9 0.054(6) 0.085(8) 0.038(6) 0.005(6) 0.007(5) 0.011(6) C10 0.062(7) 0.084(9) 0.058(8) 0.020(6) 0.004(6) 0.003(6) C11 0.074(8) 0.099(9) 0.054(7) 0.027(7) 0.009(6) 0.032(7) C12 0.042(6) 0.054(6) 0.050(6) 0.019(5) -0.001(5) 0.013(4) C13 0.040(5) 0.045(5) 0.035(5) 0.005(4) -0.001(4) 0.005(4) C14 0.035(5) 0.046(5) 0.060(6) -0.001(4) 0.013(4) -0.010(4) C15 0.045(5) 0.069(6) 0.089(8) 0.004(10) 0.024(9) 0.000(4) C16 0.044(5) 0.075(7) 0.078(11) 0.010(7) 0.023(6) 0.017(5) C17 0.061(5) 0.054(5) 0.069(6) -0.008(7) 0.021(9) 0.011(4) C18 0.028(5) 0.060(6) 0.073(7) -0.002(5) 0.006(4) 0.000(4) C19 0.067(6) 0.032(5) 0.030(5) 0.008(4) 0.007(4) -0.007(4) C20 0.038(5) 0.045(5) 0.042(5) -0.009(4) 0.006(4) -0.008(4) C21 0.056(6) 0.065(7) 0.053(7) -0.014(5) 0.010(5) -0.020(5) C22 0.054(7) 0.077(8) 0.055(7) -0.024(6) -0.002(5) -0.022(6) C23 0.032(5) 0.088(8) 0.055(7) -0.005(6) -0.005(5) -0.011(5) C24 0.038(5) 0.063(7) 0.036(6) -0.004(4) 0.004(4) -0.004(4) C25 0.032(4) 0.039(5) 0.035(5) -0.004(4) -0.005(3) 0.004(4) C26 0.035(5) 0.037(5) 0.046(5) 0.002(4) 0.006(4) -0.003(3) C27 0.055(6) 0.031(5) 0.060(7) -0.006(4) -0.002(5) 0.007(4) C28 0.043(5) 0.045(5) 0.049(6) -0.008(5) -0.004(5) 0.015(4) C29 0.044(5) 0.075(8) 0.053(7) 0.004(6) 0.019(5) 0.015(5) C30 0.045(5) 0.034(5) 0.077(7) 0.008(5) 0.023(5) 0.000(4) C31 0.060(6) 0.064(7) 0.066(8) -0.019(6) 0.001(6) 0.028(6) N99 0.078(8) 0.067(7) 0.079(8) 0.004(6) -0.002(6) 0.006(6) C98 0.067(8) 0.057(7) 0.047(7) -0.005(5) -0.003(6) 0.006(6) C99 0.089(11) 0.097(11) 0.100(13) -0.005(9) 0.036(10) -0.001(8) _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 N2 1.708(6) . ? Re1 O1 2.035(6) . ? Re1 N1 2.156(8) . ? Re1 Cl1 2.389(2) . ? Re1 Cl2 2.420(3) . ? Re1 P1 2.433(2) . ? N1 C20 1.328(12) . ? N1 C24 1.352(12) . ? N2 C25 1.393(10) . ? O1 C19 1.303(11) . ? O2 C19 1.210(11) . ? P1 C7 1.819(9) . ? P1 C13 1.824(9) . ? P1 C1 1.840(8) . ? C1 C6 1.372(13) . ? C1 C2 1.374(13) . ? C2 C3 1.396(15) . ? C3 C4 1.353(19) . ? C4 C5 1.336(18) . ? C5 C6 1.386(14) . ? C7 C8 1.381(12) . ? C7 C12 1.387(12) . ? C8 C9 1.368(15) . ? C9 C10 1.361(16) . ? C10 C11 1.372(17) . ? C11 C12 1.376(15) . ? C13 C18 1.384(16) . ? C13 C14 1.387(13) . ? C14 C15 1.369(14) . ? C15 C16 1.357(15) . ? C16 C17 1.389(14) . ? C17 C18 1.371(13) . ? C19 C20 1.481(13) . ? C20 C21 1.383(13) . ? C21 C22 1.346(16) . ? C22 C23 1.382(18) . ? C23 C24 1.390(14) . ? C25 C30 1.389(12) . ? C25 C26 1.389(11) . ? C26 C27 1.387(13) . ? C27 C28 1.358(15) . ? C28 C29 1.373(17) . ? C28 C31 1.517(13) . ? C29 C30 1.380(14) . ? N99 C98 1.102(15) . ? C98 C99 1.41(2) . ? 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 N2 Re1 O1 172.1(3) . . ? N2 Re1 N1 100.5(3) . . ? O1 Re1 N1 75.6(3) . . ? N2 Re1 Cl1 101.1(2) . . ? O1 Re1 Cl1 85.8(2) . . ? N1 Re1 Cl1 88.2(2) . . ? N2 Re1 Cl2 91.3(2) . . ? O1 Re1 Cl2 81.5(2) . . ? N1 Re1 Cl2 84.1(2) . . ? Cl1 Re1 Cl2 166.47(9) . . ? N2 Re1 P1 96.9(2) . . ? O1 Re1 P1 87.14(18) . . ? N1 Re1 P1 162.6(2) . . ? Cl1 Re1 P1 88.53(8) . . ? Cl2 Re1 P1 95.47(10) . . ? C20 N1 C24 120.4(8) . . ? C20 N1 Re1 114.5(6) . . ? C24 N1 Re1 125.0(7) . . ? C25 N2 Re1 167.9(6) . . ? C19 O1 Re1 120.2(6) . . ? C7 P1 C13 105.2(4) . . ? C7 P1 C1 102.7(4) . . ? C13 P1 C1 105.5(4) . . ? C7 P1 Re1 117.1(3) . . ? C13 P1 Re1 111.9(3) . . ? C1 P1 Re1 113.3(3) . . ? C6 C1 C2 119.3(8) . . ? C6 C1 P1 120.2(7) . . ? C2 C1 P1 120.5(7) . . ? C1 C2 C3 120.1(10) . . ? C4 C3 C2 118.7(11) . . ? C5 C4 C3 122.1(11) . . ? C4 C5 C6 119.9(12) . . ? C1 C6 C5 119.8(11) . . ? C8 C7 C12 119.6(9) . . ? C8 C7 P1 118.3(6) . . ? C12 C7 P1 121.8(7) . . ? C9 C8 C7 120.0(9) . . ? C10 C9 C8 120.6(11) . . ? C9 C10 C11 120.0(12) . . ? C10 C11 C12 120.5(11) . . ? C11 C12 C7 119.3(10) . . ? C18 C13 C14 118.3(8) . . ? C18 C13 P1 119.7(7) . . ? C14 C13 P1 121.8(8) . . ? C15 C14 C13 119.7(9) . . ? C16 C15 C14 121.7(9) . . ? C15 C16 C17 119.7(9) . . ? C18 C17 C16 118.8(9) . . ? C17 C18 C13 121.8(9) . . ? O2 C19 O1 123.8(9) . . ? O2 C19 C20 122.0(9) . . ? O1 C19 C20 114.1(8) . . ? N1 C20 C21 121.1(9) . . ? N1 C20 C19 114.7(8) . . ? C21 C20 C19 124.2(10) . . ? C22 C21 C20 119.9(11) . . ? C21 C22 C23 119.3(10) . . ? C22 C23 C24 119.7(11) . . ? N1 C24 C23 119.5(10) . . ? C30 C25 C26 119.7(8) . . ? C30 C25 N2 118.3(8) . . ? C26 C25 N2 121.9(8) . . ? C27 C26 C25 118.5(8) . . ? C28 C27 C26 122.4(9) . . ? C27 C28 C29 118.6(8) . . ? C27 C28 C31 120.7(10) . . ? C29 C28 C31 120.6(10) . . ? C28 C29 C30 121.3(9) . . ? C29 C30 C25 119.5(9) . . ? N99 C98 C99 178.1(14) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.449 _refine_diff_density_min -1.347 _refine_diff_density_rms 0.098 _database_code_depnum_ccdc_archive 'CCDC 899354' ####################################################################### # # 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_ren265 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H26 Br2 N2 O2 P Re' _chemical_formula_sum 'C31 H26 Br2 N2 O2 P Re' _chemical_formula_weight 835.53 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' Br Br -0.2901 2.4595 '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 Cc 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' _cell_length_a 15.7245(12) _cell_length_b 14.0954(11) _cell_length_c 13.5539(10) _cell_angle_alpha 90.00 _cell_angle_beta 98.885(7) _cell_angle_gamma 90.00 _cell_volume 2968.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2853 _cell_measurement_theta_min 3.43 _cell_measurement_theta_max 29.30 _exptl_crystal_description polyhedron _exptl_crystal_colour green _exptl_crystal_size_max 0.249 _exptl_crystal_size_mid 0.133 _exptl_crystal_size_min 0.019 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.870 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1608 _exptl_absorpt_coefficient_mu 6.871 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.396 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ;CrysAlis RED, (2005) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293.0(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 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6801 _diffrn_reflns_av_R_equivalents 0.0510 _diffrn_reflns_av_unetI/netI 0.0746 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4156 _reflns_number_gt 3784 _reflns_threshold_expression >2sigma(I) #========================================================================== # # REFINEMENT DATA _computing_data_collection 'CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000)' _computing_cell_refinement 'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)' _computing_data_reduction 'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;XP in SHELXTL/PC (Sheldrick, 1990b) ORTEP-3 W v. 1.062 (Farrugia 1997) ; _computing_publication_material ;SHELXL-97 (Sheldrick, 1997) and PLATON (Spek, 1990) ; _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^)+(0.0424P)^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 0.041(14) _refine_ls_number_reflns 4156 _refine_ls_number_parameters 353 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0499 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.0987 _refine_ls_wR_factor_gt 0.0930 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 0.29910(2) 0.32652(3) 0.87245(2) 0.03398(14) Uani 1 1 d . . . N1 N 0.3910(6) 0.4132(8) 0.9619(6) 0.040(2) Uani 1 1 d . . . N2 N 0.2189(7) 0.3392(7) 0.9432(9) 0.033(3) Uani 1 1 d . . . O1 O 0.4058(6) 0.3246(5) 0.7994(7) 0.036(2) Uani 1 1 d . . . O2 O 0.5370(5) 0.3756(8) 0.7946(6) 0.052(2) Uani 1 1 d . . . P1 P 0.2097(2) 0.2295(2) 0.7469(2) 0.0345(8) Uani 1 1 d . . . Br1 Br 0.25799(9) 0.47402(9) 0.76691(9) 0.0467(3) Uani 1 1 d . . . Br2 Br 0.37584(10) 0.19038(12) 0.97186(12) 0.0620(5) Uani 1 1 d . . . C1 C 0.0985(8) 0.2335(10) 0.7696(8) 0.043(3) Uani 1 1 d . . . C2 C 0.0608(9) 0.3201(9) 0.7760(10) 0.053(4) Uani 1 1 d . . . H2 H 0.0922 0.3750 0.7693 0.063 Uiso 1 1 calc R . . C3 C -0.0246(10) 0.3268(11) 0.7924(14) 0.072(5) Uani 1 1 d . . . H3 H -0.0503 0.3856 0.7976 0.086 Uiso 1 1 calc R . . C4 C -0.0700(9) 0.2438(13) 0.8010(12) 0.071(5) Uani 1 1 d . . . H4 H -0.1268 0.2471 0.8124 0.085 Uiso 1 1 calc R . . C5 C -0.0339(12) 0.1599(13) 0.7931(17) 0.080(6) Uani 1 1 d . . . H5 H -0.0659 0.1052 0.7988 0.096 Uiso 1 1 calc R . . C6 C 0.0496(8) 0.1521(11) 0.7768(11) 0.057(4) Uani 1 1 d . . . H6 H 0.0736 0.0925 0.7705 0.068 Uiso 1 1 calc R . . C7 C 0.2047(7) 0.2678(8) 0.6186(8) 0.035(3) Uani 1 1 d . . . C8 C 0.1288(9) 0.2712(9) 0.5534(9) 0.051(3) Uani 1 1 d . . . H8 H 0.0772 0.2574 0.5759 0.061 Uiso 1 1 calc R . . C9 C 0.1283(12) 0.2946(12) 0.4562(11) 0.060(4) Uani 1 1 d . . . H9 H 0.0762 0.2964 0.4131 0.072 Uiso 1 1 calc R . . C10 C 0.2024(13) 0.3157(11) 0.4200(10) 0.073(5) Uani 1 1 d . . . H10 H 0.2007 0.3301 0.3527 0.087 Uiso 1 1 calc R . . C11 C 0.2793(11) 0.3155(11) 0.4834(11) 0.067(4) Uani 1 1 d . . . H11 H 0.3299 0.3316 0.4598 0.080 Uiso 1 1 calc R . . C12 C 0.2814(9) 0.2908(12) 0.5843(9) 0.059(4) Uani 1 1 d . . . H12 H 0.3333 0.2898 0.6277 0.071 Uiso 1 1 calc R . . C13 C 0.2308(8) 0.1034(10) 0.7419(9) 0.049(3) Uani 1 1 d . . . C14 C 0.2454(9) 0.0580(10) 0.6529(11) 0.058(4) Uani 1 1 d . . . H14 H 0.2467 0.0940 0.5956 0.070 Uiso 1 1 calc R . . C15 C 0.2576(10) -0.0369(13) 0.6500(15) 0.077(5) Uani 1 1 d . . . H15 H 0.2671 -0.0660 0.5911 0.093 Uiso 1 1 calc R . . C16 C 0.2557(11) -0.0911(13) 0.7364(18) 0.089(6) Uani 1 1 d . . . H16 H 0.2623 -0.1566 0.7340 0.107 Uiso 1 1 calc R . . C17 C 0.2444(10) -0.0491(10) 0.8228(15) 0.073(5) Uani 1 1 d . . . H17 H 0.2448 -0.0853 0.8802 0.088 Uiso 1 1 calc R . . C18 C 0.2323(9) 0.0479(10) 0.8261(12) 0.062(4) Uani 1 1 d . . . H18 H 0.2251 0.0764 0.8862 0.074 Uiso 1 1 calc R . . C19 C 0.4734(7) 0.3715(8) 0.8346(8) 0.031(3) Uani 1 1 d . . . C20 C 0.4664(7) 0.4216(8) 0.9287(8) 0.035(3) Uani 1 1 d . . . C21 C 0.5325(8) 0.4760(10) 0.9809(10) 0.051(3) Uani 1 1 d . . . H21 H 0.5852 0.4800 0.9580 0.061 Uiso 1 1 calc R . . C22 C 0.5205(9) 0.5229(10) 1.0647(9) 0.053(4) Uani 1 1 d . . . H22 H 0.5644 0.5592 1.1001 0.064 Uiso 1 1 calc R . . C23 C 0.4415(10) 0.5158(11) 1.0966(10) 0.061(4) Uani 1 1 d . . . H23 H 0.4305 0.5484 1.1530 0.074 Uiso 1 1 calc R . . C24 C 0.3807(9) 0.4606(12) 1.0444(9) 0.059(4) Uani 1 1 d . . . H24 H 0.3282 0.4551 1.0673 0.071 Uiso 1 1 calc R . . C25 C 0.1617(8) 0.3554(9) 1.0076(9) 0.040(3) Uani 1 1 d . . . C26 C 0.1228(10) 0.4435(10) 1.0097(10) 0.057(4) Uani 1 1 d . . . H26 H 0.1367 0.4923 0.9689 0.069 Uiso 1 1 calc R . . C27 C 0.0639(10) 0.4580(11) 1.0721(11) 0.064(4) Uani 1 1 d . . . H27 H 0.0367 0.5166 1.0715 0.076 Uiso 1 1 calc R . . C28 C 0.0433(9) 0.3890(11) 1.1359(10) 0.052(3) Uani 1 1 d . . . C29 C 0.0801(10) 0.3011(11) 1.1315(11) 0.060(4) Uani 1 1 d . . . H29 H 0.0647 0.2526 1.1718 0.072 Uiso 1 1 calc R . . C30 C 0.1382(9) 0.2834(10) 1.0699(9) 0.053(4) Uani 1 1 d . . . H30 H 0.1627 0.2235 1.0687 0.064 Uiso 1 1 calc R . . C31 C -0.0186(11) 0.4041(13) 1.2094(13) 0.083(5) Uani 1 1 d . . . H31A H 0.0123 0.4272 1.2714 0.125 Uiso 1 1 calc R . . H31B H -0.0460 0.3451 1.2207 0.125 Uiso 1 1 calc R . . H31C H -0.0615 0.4497 1.1828 0.125 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 0.0313(2) 0.0402(2) 0.0314(2) -0.0033(2) 0.00810(15) -0.0038(3) N1 0.034(6) 0.059(7) 0.025(5) -0.003(5) -0.004(4) 0.012(5) N2 0.024(6) 0.037(6) 0.041(6) 0.002(4) 0.010(5) 0.010(5) O1 0.034(6) 0.042(5) 0.032(5) -0.006(3) 0.008(4) -0.005(4) O2 0.033(5) 0.081(7) 0.045(5) -0.001(5) 0.013(4) 0.002(5) P1 0.0267(16) 0.043(2) 0.0343(16) -0.0057(14) 0.0049(13) -0.0043(15) Br1 0.0511(8) 0.0404(7) 0.0490(7) 0.0006(6) 0.0095(6) 0.0008(7) Br2 0.0521(10) 0.0628(10) 0.0670(10) 0.0205(8) -0.0038(8) -0.0043(8) C1 0.044(7) 0.052(9) 0.035(6) 0.002(6) 0.006(5) 0.003(7) C2 0.047(9) 0.049(9) 0.061(9) 0.011(6) 0.002(7) 0.002(7) C3 0.037(9) 0.063(11) 0.117(14) 0.023(9) 0.020(9) 0.014(8) C4 0.034(8) 0.086(13) 0.094(12) 0.030(10) 0.014(8) -0.005(9) C5 0.043(10) 0.073(12) 0.126(17) 0.046(12) 0.019(10) 0.006(9) C6 0.031(8) 0.058(9) 0.082(10) 0.013(7) 0.011(7) -0.013(7) C7 0.033(6) 0.032(6) 0.039(6) -0.010(5) 0.011(5) -0.024(5) C8 0.062(9) 0.050(8) 0.036(7) -0.008(6) -0.003(6) 0.006(7) C9 0.071(12) 0.053(9) 0.052(9) 0.007(8) -0.007(8) -0.018(9) C10 0.115(16) 0.072(12) 0.032(7) -0.010(7) 0.012(9) -0.015(10) C11 0.060(10) 0.088(12) 0.057(9) -0.009(8) 0.025(8) -0.026(8) C12 0.044(8) 0.094(12) 0.039(7) -0.003(7) 0.005(6) -0.014(8) C13 0.048(8) 0.052(8) 0.040(7) 0.006(6) -0.015(6) -0.013(7) C14 0.047(8) 0.047(8) 0.080(10) -0.033(7) 0.008(7) -0.008(7) C15 0.052(10) 0.077(12) 0.100(13) -0.048(11) 0.001(9) 0.012(9) C16 0.053(10) 0.050(11) 0.15(2) -0.020(13) -0.026(12) -0.001(8) C17 0.069(11) 0.030(8) 0.112(14) 0.019(9) -0.010(10) -0.008(8) C18 0.053(9) 0.051(9) 0.078(10) -0.004(8) -0.002(7) 0.005(7) C19 0.028(6) 0.026(6) 0.037(6) 0.007(5) 0.000(5) 0.000(5) C20 0.038(7) 0.029(6) 0.037(6) 0.000(5) 0.006(5) -0.002(5) C21 0.034(7) 0.058(9) 0.059(8) 0.004(7) 0.007(6) -0.002(7) C22 0.061(10) 0.045(9) 0.049(9) -0.014(6) -0.007(7) -0.017(7) C23 0.068(10) 0.073(10) 0.038(7) -0.016(7) -0.008(7) 0.003(9) C24 0.046(8) 0.098(12) 0.030(7) -0.017(7) -0.004(6) 0.018(8) C25 0.033(7) 0.051(8) 0.036(6) -0.001(6) 0.007(5) 0.003(6) C26 0.075(10) 0.045(8) 0.058(8) 0.008(7) 0.030(7) 0.010(8) C27 0.056(9) 0.053(10) 0.087(11) 0.000(8) 0.024(8) 0.006(8) C28 0.045(8) 0.059(9) 0.055(8) -0.016(7) 0.017(6) -0.007(7) C29 0.071(11) 0.046(9) 0.074(10) 0.010(7) 0.042(9) 0.002(8) C30 0.065(9) 0.042(8) 0.058(8) 0.017(7) 0.028(7) 0.015(7) C31 0.076(11) 0.076(12) 0.110(13) -0.010(11) 0.053(10) -0.004(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 N2 1.708(11) . ? Re1 O1 2.076(9) . ? Re1 N1 2.124(10) . ? Re1 P1 2.450(3) . ? Re1 Br2 2.5401(16) . ? Re1 Br1 2.5497(14) . ? N1 C24 1.333(15) . ? N1 C20 1.336(14) . ? N2 C25 1.365(15) . ? O1 C19 1.279(13) . ? O2 C19 1.210(13) . ? P1 C7 1.810(11) . ? P1 C13 1.812(15) . ? P1 C1 1.822(13) . ? C1 C2 1.366(18) . ? C1 C6 1.393(19) . ? C2 C3 1.40(2) . ? C3 C4 1.38(2) . ? C4 C5 1.32(2) . ? C5 C6 1.37(2) . ? C7 C8 1.373(16) . ? C7 C12 1.396(16) . ? C8 C9 1.357(19) . ? C9 C10 1.36(2) . ? C10 C11 1.37(2) . ? C11 C12 1.406(19) . ? C13 C18 1.381(18) . ? C13 C14 1.414(18) . ? C14 C15 1.35(2) . ? C15 C16 1.40(2) . ? C16 C17 1.35(2) . ? C17 C18 1.38(2) . ? C19 C20 1.477(15) . ? C20 C21 1.394(17) . ? C21 C22 1.353(17) . ? C22 C23 1.381(19) . ? C23 C24 1.35(2) . ? C25 C26 1.387(19) . ? C25 C30 1.404(17) . ? C26 C27 1.363(18) . ? C27 C28 1.373(19) . ? C28 C29 1.37(2) . ? C28 C31 1.512(19) . ? C29 C30 1.353(17) . ? 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 N2 Re1 O1 172.2(5) . . ? N2 Re1 N1 96.6(5) . . ? O1 Re1 N1 75.6(3) . . ? N2 Re1 P1 93.1(4) . . ? O1 Re1 P1 94.6(2) . . ? N1 Re1 P1 169.9(3) . . ? N2 Re1 Br2 96.5(4) . . ? O1 Re1 Br2 83.7(2) . . ? N1 Re1 Br2 84.6(3) . . ? P1 Re1 Br2 96.98(10) . . ? N2 Re1 Br1 94.8(3) . . ? O1 Re1 Br1 84.1(2) . . ? N1 Re1 Br1 86.7(3) . . ? P1 Re1 Br1 89.82(9) . . ? Br2 Re1 Br1 166.45(5) . . ? C24 N1 C20 117.9(11) . . ? C24 N1 Re1 127.4(9) . . ? C20 N1 Re1 114.8(7) . . ? C25 N2 Re1 173.1(10) . . ? C19 O1 Re1 120.1(8) . . ? C7 P1 C13 103.7(5) . . ? C7 P1 C1 104.6(5) . . ? C13 P1 C1 102.9(6) . . ? C7 P1 Re1 115.9(3) . . ? C13 P1 Re1 119.0(4) . . ? C1 P1 Re1 109.2(4) . . ? C2 C1 C6 118.8(13) . . ? C2 C1 P1 118.4(11) . . ? C6 C1 P1 122.8(11) . . ? C1 C2 C3 120.6(13) . . ? C4 C3 C2 118.5(14) . . ? C5 C4 C3 120.9(15) . . ? C4 C5 C6 121.3(17) . . ? C5 C6 C1 119.9(15) . . ? C8 C7 C12 119.1(11) . . ? C8 C7 P1 122.3(9) . . ? C12 C7 P1 118.5(9) . . ? C9 C8 C7 120.5(14) . . ? C8 C9 C10 121.7(15) . . ? C9 C10 C11 119.5(14) . . ? C10 C11 C12 119.7(14) . . ? C7 C12 C11 119.4(12) . . ? C18 C13 C14 117.7(13) . . ? C18 C13 P1 120.3(10) . . ? C14 C13 P1 122.0(10) . . ? C15 C14 C13 120.9(16) . . ? C14 C15 C16 119.5(16) . . ? C17 C16 C15 120.6(16) . . ? C16 C17 C18 120.0(17) . . ? C13 C18 C17 121.2(16) . . ? O2 C19 O1 123.6(11) . . ? O2 C19 C20 122.7(10) . . ? O1 C19 C20 113.6(10) . . ? N1 C20 C21 120.6(10) . . ? N1 C20 C19 115.9(10) . . ? C21 C20 C19 123.5(11) . . ? C22 C21 C20 120.3(12) . . ? C21 C22 C23 118.4(12) . . ? C24 C23 C22 118.5(13) . . ? N1 C24 C23 124.3(14) . . ? N2 C25 C26 119.9(11) . . ? N2 C25 C30 121.6(12) . . ? C26 C25 C30 118.4(12) . . ? C27 C26 C25 119.5(13) . . ? C26 C27 C28 122.2(14) . . ? C29 C28 C27 118.0(13) . . ? C29 C28 C31 118.4(13) . . ? C27 C28 C31 123.6(14) . . ? C30 C29 C28 121.5(13) . . ? C29 C30 C25 120.2(13) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.411 _refine_diff_density_min -1.290 _refine_diff_density_rms 0.145 _database_code_depnum_ccdc_archive 'CCDC 899355' ####################################################################### # # 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_ren281a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H26 Cl2 N2 O2 P Re' _chemical_formula_sum 'C31 H26 Cl2 N2 O2 P Re' _chemical_formula_weight 746.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n 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 9.7816(5) _cell_length_b 14.8808(8) _cell_length_c 21.8833(14) _cell_angle_alpha 90.00 _cell_angle_beta 102.709(6) _cell_angle_gamma 90.00 _cell_volume 3107.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8390 _cell_measurement_theta_min 3.3310 _cell_measurement_theta_max 29.2028 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.113 _exptl_crystal_size_mid 0.048 _exptl_crystal_size_min 0.022 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.596 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1464 _exptl_absorpt_coefficient_mu 4.164 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details ;CrysAlis RED, (2005) ; _exptl_absorpt_correction_T_min 0.396 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21233 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_unetI/netI 0.0433 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5463 _reflns_number_gt 4312 _reflns_threshold_expression >2sigma(I) #========================================================================== # # REFINEMENT DATA _computing_data_collection 'CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000)' _computing_cell_refinement 'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)' _computing_data_reduction 'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;XP in SHELXTL/PC (Sheldrick, 1990b) ORTEP-3 W v. 1.062 (Farrugia 1997) ; _computing_publication_material ;SHELXL-97 (Sheldrick, 1997) and PLATON (Spek, 1990) ; _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^)+(0.0267P)^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 5463 _refine_ls_number_parameters 353 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0583 _refine_ls_wR_factor_gt 0.0549 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.988 _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 0.963315(15) 0.173905(11) 0.226766(8) 0.03814(7) Uani 1 1 d . . . N1 N 1.1829(3) 0.1894(2) 0.25243(15) 0.0365(8) Uani 1 1 d . . . N2 N 0.9284(3) 0.2777(2) 0.19376(17) 0.0472(9) Uani 1 1 d . . . O1 O 1.0370(2) 0.04720(18) 0.25649(12) 0.0406(7) Uani 1 1 d . . . O2 O 1.2212(3) -0.0345(2) 0.30302(17) 0.0728(10) Uani 1 1 d . . . P1 P 0.96041(10) 0.10159(7) 0.12643(5) 0.0366(2) Uani 1 1 d . . . Cl1 Cl 0.97953(12) 0.20306(9) 0.33566(6) 0.0646(3) Uani 1 1 d . . . Cl2 Cl 0.73108(11) 0.12539(10) 0.22002(6) 0.0668(4) Uani 1 1 d . . . C1 C 1.1354(4) 0.0626(3) 0.12371(18) 0.0393(10) Uani 1 1 d . . . C2 C 1.2414(4) 0.1262(3) 0.12737(19) 0.0482(11) Uani 1 1 d . . . H2 H 1.2193 0.1870 0.1258 0.058 Uiso 1 1 calc R . . C3 C 1.3782(5) 0.0997(4) 0.1333(2) 0.0636(15) Uani 1 1 d . . . H3 H 1.4482 0.1426 0.1353 0.076 Uiso 1 1 calc R . . C4 C 1.4115(5) 0.0101(5) 0.1363(2) 0.0764(18) Uani 1 1 d . . . H4 H 1.5046 -0.0077 0.1416 0.092 Uiso 1 1 calc R . . C5 C 1.3089(5) -0.0530(4) 0.1316(2) 0.0704(15) Uani 1 1 d . . . H5 H 1.3320 -0.1137 0.1325 0.085 Uiso 1 1 calc R . . C6 C 1.1694(4) -0.0271(3) 0.1253(2) 0.0540(12) Uani 1 1 d . . . H6 H 1.0997 -0.0704 0.1223 0.065 Uiso 1 1 calc R . . C7 C 0.8468(4) 0.0036(3) 0.10785(19) 0.0394(10) Uani 1 1 d . . . C8 C 0.8328(4) -0.0576(3) 0.1530(2) 0.0507(11) Uani 1 1 d . . . H8 H 0.8821 -0.0490 0.1940 0.061 Uiso 1 1 calc R . . C9 C 0.7476(4) -0.1314(3) 0.1387(2) 0.0555(12) Uani 1 1 d . . . H9 H 0.7417 -0.1730 0.1698 0.067 Uiso 1 1 calc R . . C10 C 0.6719(5) -0.1440(3) 0.0796(2) 0.0596(13) Uani 1 1 d . . . H10 H 0.6137 -0.1938 0.0704 0.072 Uiso 1 1 calc R . . C11 C 0.6806(5) -0.0835(4) 0.0333(2) 0.0695(15) Uani 1 1 d . . . H11 H 0.6277 -0.0918 -0.0071 0.083 Uiso 1 1 calc R . . C12 C 0.7692(5) -0.0097(3) 0.0473(2) 0.0589(13) Uani 1 1 d . . . H12 H 0.7766 0.0309 0.0159 0.071 Uiso 1 1 calc R . . C13 C 0.9019(4) 0.1749(3) 0.0593(2) 0.0442(10) Uani 1 1 d . . . C14 C 0.9789(5) 0.1888(3) 0.0136(2) 0.0608(13) Uani 1 1 d . . . H14 H 1.0655 0.1610 0.0172 0.073 Uiso 1 1 calc R . . C15 C 0.9270(7) 0.2437(4) -0.0366(3) 0.0875(18) Uani 1 1 d . . . H15 H 0.9798 0.2535 -0.0665 0.105 Uiso 1 1 calc R . . C16 C 0.8004(8) 0.2836(4) -0.0433(3) 0.096(2) Uani 1 1 d . . . H16 H 0.7667 0.3202 -0.0778 0.115 Uiso 1 1 calc R . . C17 C 0.7208(6) 0.2701(4) 0.0010(3) 0.0845(18) Uani 1 1 d . . . H17 H 0.6334 0.2972 -0.0038 0.101 Uiso 1 1 calc R . . C18 C 0.7721(5) 0.2159(3) 0.0526(2) 0.0609(13) Uani 1 1 d . . . H18 H 0.7194 0.2070 0.0827 0.073 Uiso 1 1 calc R . . C19 C 1.1704(4) 0.0352(3) 0.2808(2) 0.0437(10) Uani 1 1 d . . . C20 C 1.2562(4) 0.1167(3) 0.27765(18) 0.0377(10) Uani 1 1 d . . . C21 C 1.3999(4) 0.1183(3) 0.2975(2) 0.0484(11) Uani 1 1 d . . . H21 H 1.4483 0.0669 0.3140 0.058 Uiso 1 1 calc R . . C22 C 1.4709(4) 0.1964(4) 0.2927(2) 0.0597(14) Uani 1 1 d . . . H22 H 1.5680 0.1987 0.3053 0.072 Uiso 1 1 calc R . . C23 C 1.3960(5) 0.2712(3) 0.2691(2) 0.0571(13) Uani 1 1 d . . . H23 H 1.4419 0.3252 0.2662 0.069 Uiso 1 1 calc R . . C24 C 1.2529(4) 0.2661(3) 0.2496(2) 0.0484(11) Uani 1 1 d . . . H24 H 1.2031 0.3174 0.2340 0.058 Uiso 1 1 calc R . . C25 C 0.8923(5) 0.3577(3) 0.1620(2) 0.0521(11) Uani 1 1 d . . . C26 C 0.7774(6) 0.4051(4) 0.1724(3) 0.0800(17) Uani 1 1 d . . . H26 H 0.7312 0.3865 0.2030 0.096 Uiso 1 1 calc R . . C27 C 0.7328(7) 0.4800(4) 0.1366(3) 0.095(2) Uani 1 1 d . . . H27 H 0.6545 0.5109 0.1431 0.114 Uiso 1 1 calc R . . C28 C 0.7990(7) 0.5102(4) 0.0926(3) 0.0858(17) Uani 1 1 d . . . C29 C 0.9155(6) 0.4647(4) 0.0845(3) 0.0806(16) Uani 1 1 d . . . H29 H 0.9634 0.4853 0.0550 0.097 Uiso 1 1 calc R . . C30 C 0.9637(5) 0.3892(3) 0.1190(2) 0.0629(13) Uani 1 1 d . . . H30 H 1.0439 0.3599 0.1132 0.075 Uiso 1 1 calc R . . C31 C 0.7446(9) 0.5921(5) 0.0527(4) 0.146(3) Uani 1 1 d . . . H31A H 0.6456 0.5860 0.0365 0.219 Uiso 1 1 calc R . . H31B H 0.7915 0.5965 0.0186 0.219 Uiso 1 1 calc R . . H31C H 0.7626 0.6453 0.0780 0.219 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 0.02975(10) 0.04151(11) 0.04181(12) -0.00359(9) 0.00491(7) 0.00859(7) N1 0.0324(17) 0.038(2) 0.038(2) -0.0054(16) 0.0051(14) 0.0016(14) N2 0.043(2) 0.042(2) 0.053(2) -0.0088(19) 0.0020(16) 0.0133(16) O1 0.0344(15) 0.0413(17) 0.0437(18) 0.0033(13) 0.0035(13) 0.0023(12) O2 0.063(2) 0.044(2) 0.098(3) 0.013(2) -0.0093(18) 0.0121(16) P1 0.0301(5) 0.0386(6) 0.0397(7) -0.0002(5) 0.0048(4) -0.0001(4) Cl1 0.0623(7) 0.0834(9) 0.0487(8) -0.0159(7) 0.0136(6) 0.0159(6) Cl2 0.0314(6) 0.0986(10) 0.0717(9) -0.0064(8) 0.0140(5) 0.0028(6) C1 0.035(2) 0.053(3) 0.030(2) -0.004(2) 0.0071(17) 0.0030(19) C2 0.035(2) 0.070(3) 0.041(3) -0.013(2) 0.0106(19) -0.006(2) C3 0.042(3) 0.104(5) 0.047(3) -0.014(3) 0.014(2) -0.008(3) C4 0.044(3) 0.126(6) 0.060(4) -0.011(4) 0.012(2) 0.020(3) C5 0.066(3) 0.077(4) 0.069(4) -0.002(3) 0.017(3) 0.029(3) C6 0.051(3) 0.056(3) 0.056(3) -0.003(3) 0.014(2) 0.013(2) C7 0.033(2) 0.039(3) 0.047(3) -0.002(2) 0.0103(19) -0.0035(17) C8 0.042(2) 0.048(3) 0.054(3) 0.004(2) -0.006(2) -0.006(2) C9 0.049(3) 0.052(3) 0.061(4) 0.005(3) 0.004(2) -0.008(2) C10 0.060(3) 0.052(3) 0.068(4) -0.012(3) 0.017(3) -0.020(2) C11 0.087(4) 0.072(4) 0.047(3) -0.014(3) 0.010(3) -0.033(3) C12 0.074(3) 0.065(3) 0.041(3) -0.009(3) 0.018(2) -0.027(3) C13 0.046(2) 0.041(2) 0.041(3) 0.000(2) -0.0025(19) -0.008(2) C14 0.069(3) 0.065(4) 0.043(3) 0.004(3) 0.001(2) -0.013(2) C15 0.110(5) 0.095(5) 0.048(4) 0.017(4) -0.004(3) -0.024(4) C16 0.119(6) 0.080(5) 0.065(5) 0.024(4) -0.032(4) -0.021(4) C17 0.072(4) 0.068(4) 0.089(5) 0.012(4) -0.035(3) 0.005(3) C18 0.049(3) 0.059(3) 0.065(4) 0.003(3) -0.009(2) -0.001(2) C19 0.045(3) 0.039(3) 0.044(3) -0.002(2) 0.004(2) 0.008(2) C20 0.035(2) 0.043(3) 0.034(2) -0.004(2) 0.0035(17) 0.0084(18) C21 0.036(2) 0.058(3) 0.048(3) -0.008(2) 0.0016(19) 0.008(2) C22 0.030(2) 0.088(4) 0.059(3) -0.015(3) 0.006(2) -0.005(2) C23 0.049(3) 0.059(3) 0.062(3) -0.012(3) 0.008(2) -0.019(2) C24 0.048(3) 0.039(3) 0.055(3) -0.008(2) 0.005(2) -0.003(2) C25 0.061(3) 0.039(3) 0.052(3) -0.008(2) 0.001(2) 0.009(2) C26 0.097(4) 0.072(4) 0.073(4) 0.011(3) 0.023(3) 0.049(3) C27 0.106(5) 0.071(4) 0.103(5) 0.008(4) 0.013(4) 0.047(4) C28 0.111(5) 0.057(4) 0.074(5) 0.002(3) -0.011(4) 0.012(4) C29 0.107(5) 0.061(4) 0.069(4) 0.007(3) 0.009(3) -0.016(3) C30 0.064(3) 0.045(3) 0.072(4) -0.005(3) 0.000(3) -0.001(2) C31 0.201(8) 0.083(5) 0.135(7) 0.048(5) -0.005(6) 0.039(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 N2 1.708(4) . ? Re1 O1 2.072(3) . ? Re1 N1 2.110(3) . ? Re1 Cl2 2.3571(11) . ? Re1 Cl1 2.3928(12) . ? Re1 P1 2.4398(11) . ? N1 C24 1.339(5) . ? N1 C20 1.348(5) . ? N2 C25 1.384(6) . ? O1 C19 1.309(4) . ? O2 C19 1.204(5) . ? P1 C13 1.818(4) . ? P1 C1 1.821(4) . ? P1 C7 1.824(4) . ? C1 C6 1.373(6) . ? C1 C2 1.393(6) . ? C2 C3 1.374(6) . ? C2 H2 0.9300 . ? C3 C4 1.371(8) . ? C3 H3 0.9300 . ? C4 C5 1.361(7) . ? C4 H4 0.9300 . ? C5 C6 1.395(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.373(6) . ? C7 C12 1.389(6) . ? C8 C9 1.373(6) . ? C8 H8 0.9300 . ? C9 C10 1.354(6) . ? C9 H9 0.9300 . ? C10 C11 1.372(7) . ? C10 H10 0.9300 . ? C11 C12 1.390(6) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C18 1.387(6) . ? C13 C14 1.393(6) . ? C14 C15 1.373(7) . ? C14 H14 0.9300 . ? C15 C16 1.352(8) . ? C15 H15 0.9300 . ? C16 C17 1.385(8) . ? C16 H16 0.9300 . ? C17 C18 1.389(7) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.485(6) . ? C20 C21 1.377(5) . ? C21 C22 1.369(6) . ? C21 H21 0.9300 . ? C22 C23 1.369(7) . ? C22 H22 0.9300 . ? C23 C24 1.372(6) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C30 1.373(6) . ? C25 C26 1.387(6) . ? C26 C27 1.377(8) . ? C26 H26 0.9300 . ? C27 C28 1.351(8) . ? C27 H27 0.9300 . ? C28 C29 1.371(8) . ? C28 C31 1.524(8) . ? C29 C30 1.377(7) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Re1 O1 168.39(12) . . ? N2 Re1 N1 96.36(14) . . ? O1 Re1 N1 75.66(11) . . ? N2 Re1 Cl2 98.65(11) . . ? O1 Re1 Cl2 90.28(7) . . ? N1 Re1 Cl2 163.91(9) . . ? N2 Re1 Cl1 102.73(12) . . ? O1 Re1 Cl1 84.84(8) . . ? N1 Re1 Cl1 82.79(9) . . ? Cl2 Re1 Cl1 88.27(4) . . ? N2 Re1 P1 93.25(12) . . ? O1 Re1 P1 79.37(8) . . ? N1 Re1 P1 95.59(9) . . ? Cl2 Re1 P1 89.33(4) . . ? Cl1 Re1 P1 164.02(4) . . ? C24 N1 C20 118.1(3) . . ? C24 N1 Re1 125.6(3) . . ? C20 N1 Re1 116.1(3) . . ? C25 N2 Re1 174.4(3) . . ? C19 O1 Re1 120.0(3) . . ? C13 P1 C1 107.23(19) . . ? C13 P1 C7 103.37(19) . . ? C1 P1 C7 105.59(18) . . ? C13 P1 Re1 113.70(14) . . ? C1 P1 Re1 110.19(13) . . ? C7 P1 Re1 116.04(13) . . ? C6 C1 C2 119.1(4) . . ? C6 C1 P1 122.2(3) . . ? C2 C1 P1 118.3(3) . . ? C3 C2 C1 120.5(5) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C4 C3 C2 120.0(5) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 120.2(5) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.4(5) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 119.8(5) . . ? C1 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C8 C7 C12 118.1(4) . . ? C8 C7 P1 121.5(3) . . ? C12 C7 P1 120.3(3) . . ? C7 C8 C9 121.3(4) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C10 C9 C8 120.3(5) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 120.4(4) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C10 C11 C12 119.5(5) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C7 C12 C11 120.4(4) . . ? C7 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C18 C13 C14 119.1(4) . . ? C18 C13 P1 117.9(3) . . ? C14 C13 P1 123.0(4) . . ? C15 C14 C13 120.0(5) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C16 C15 C14 121.1(6) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C17 120.2(6) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C18 119.7(6) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? C13 C18 C17 120.0(5) . . ? C13 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? O2 C19 O1 124.6(4) . . ? O2 C19 C20 122.3(4) . . ? O1 C19 C20 113.1(4) . . ? N1 C20 C21 121.9(4) . . ? N1 C20 C19 114.8(3) . . ? C21 C20 C19 123.2(4) . . ? C22 C21 C20 119.4(4) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? C23 C22 C21 118.7(4) . . ? C23 C22 H22 120.7 . . ? C21 C22 H22 120.7 . . ? C22 C23 C24 119.8(4) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? N1 C24 C23 122.0(4) . . ? N1 C24 H24 119.0 . . ? C23 C24 H24 119.0 . . ? C30 C25 N2 121.7(4) . . ? C30 C25 C26 119.5(5) . . ? N2 C25 C26 118.8(4) . . ? C27 C26 C25 119.1(5) . . ? C27 C26 H26 120.5 . . ? C25 C26 H26 120.5 . . ? C28 C27 C26 122.2(6) . . ? C28 C27 H27 118.9 . . ? C26 C27 H27 118.9 . . ? C27 C28 C29 118.0(6) . . ? C27 C28 C31 120.8(7) . . ? C29 C28 C31 121.2(7) . . ? C28 C29 C30 121.8(5) . . ? C28 C29 H29 119.1 . . ? C30 C29 H29 119.1 . . ? C25 C30 C29 119.3(5) . . ? C25 C30 H30 120.3 . . ? C29 C30 H30 120.3 . . ? C28 C31 H31A 109.5 . . ? C28 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C28 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C8 H8 O1 0.93 2.30 3.093(5) 142.5 . C9 H9 Cl1 0.93 2.83 3.444(5) 124.9 2_645 C24 H24 O2 0.93 2.52 3.214(6) 132.1 2_755 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.767 _refine_diff_density_min -0.486 _refine_diff_density_rms 0.084 _database_code_depnum_ccdc_archive 'CCDC 899356' ####################################################################### # # 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_ren264 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H26 Br2 N2 O2 P Re, H2 O' _chemical_formula_sum 'C31 H28 Br2 N2 O3 P Re' _chemical_formula_weight 853.54 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' Br Br -0.2901 2.4595 '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 C2/c 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 41.1920(3) _cell_length_b 8.0922(3) _cell_length_c 21.8048(14) _cell_angle_alpha 90.00 _cell_angle_beta 120.786(9) _cell_angle_gamma 90.00 _cell_volume 6244.1(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5023 _cell_measurement_theta_min 3.45 _cell_measurement_theta_max 29.20 _exptl_crystal_description polyhedron _exptl_crystal_colour green _exptl_crystal_size_max 0.211 _exptl_crystal_size_mid 0.053 _exptl_crystal_size_min 0.018 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.816 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3296 _exptl_absorpt_coefficient_mu 6.537 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5230 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ;CrysAlis RED, (2005) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15231 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_unetI/netI 0.0351 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 48 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5488 _reflns_number_gt 4170 _reflns_threshold_expression >2sigma(I) #========================================================================== # # REFINEMENT DATA _computing_data_collection 'CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000)' _computing_cell_refinement 'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)' _computing_data_reduction 'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;XP in SHELXTL/PC (Sheldrick, 1990b) ORTEP-3 W v. 1.062 (Farrugia 1997) ; _computing_publication_material ;SHELXL-97 (Sheldrick, 1997) and PLATON (Spek, 1990) ; _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^)+(0.0226P)^2^+7.2362P] 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 5488 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0489 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0591 _refine_ls_wR_factor_gt 0.0551 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 0.148357(5) 0.25032(2) 0.254593(8) 0.03776(7) Uani 1 1 d . . . N1 N 0.16451(10) 0.4233(4) 0.20249(19) 0.0416(9) Uani 1 1 d . . . N2 N 0.16625(10) 0.3628(4) 0.33203(17) 0.0407(9) Uani 1 1 d . . . O1 O 0.12488(8) 0.1617(3) 0.15209(14) 0.0395(7) Uani 1 1 d . . . O2 O 0.11926(12) 0.1864(5) 0.04538(18) 0.0763(12) Uani 1 1 d . . . P1 P 0.08447(3) 0.36096(12) 0.20420(5) 0.0317(3) Uani 1 1 d . . . Br1 Br 0.208561(18) 0.10139(8) 0.28018(3) 0.0837(2) Uani 1 1 d . . . Br2 Br 0.127105(19) -0.00295(6) 0.29103(3) 0.06913(19) Uani 1 1 d . . . C1 C 0.07832(13) 0.4733(5) 0.2699(2) 0.0350(10) Uani 1 1 d . . . C2 C 0.09057(14) 0.3953(5) 0.3352(2) 0.0472(12) Uani 1 1 d . . . H2 H 0.1014 0.2908 0.3433 0.057 Uiso 1 1 calc R . . C3 C 0.08687(16) 0.4700(6) 0.3875(3) 0.0622(15) Uani 1 1 d . . . H3 H 0.0948 0.4164 0.4306 0.075 Uiso 1 1 calc R . . C4 C 0.07135(19) 0.6246(8) 0.3756(3) 0.0809(19) Uani 1 1 d . . . H4 H 0.0695 0.6773 0.4117 0.097 Uiso 1 1 calc R . . C5 C 0.05843(19) 0.7031(7) 0.3115(3) 0.0764(19) Uani 1 1 d . . . H5 H 0.0474 0.8071 0.3037 0.092 Uiso 1 1 calc R . . C6 C 0.06197(15) 0.6262(6) 0.2581(3) 0.0563(14) Uani 1 1 d . . . H6 H 0.0532 0.6787 0.2144 0.068 Uiso 1 1 calc R . . C7 C 0.04506(13) 0.2131(5) 0.1658(2) 0.0363(11) Uani 1 1 d . . . C8 C 0.01572(14) 0.2298(5) 0.1786(2) 0.0498(12) Uani 1 1 d . . . H8 H 0.0158 0.3172 0.2064 0.060 Uiso 1 1 calc R . . C9 C -0.01375(15) 0.1182(7) 0.1506(3) 0.0626(15) Uani 1 1 d . . . H9 H -0.0332 0.1296 0.1600 0.075 Uiso 1 1 calc R . . C10 C -0.01428(16) -0.0092(6) 0.1089(3) 0.0611(15) Uani 1 1 d . . . H10 H -0.0343 -0.0836 0.0895 0.073 Uiso 1 1 calc R . . C11 C 0.01461(16) -0.0276(6) 0.0957(3) 0.0605(15) Uani 1 1 d . . . H11 H 0.0143 -0.1152 0.0678 0.073 Uiso 1 1 calc R . . C12 C 0.04423(14) 0.0840(5) 0.1238(2) 0.0493(12) Uani 1 1 d . . . H12 H 0.0637 0.0717 0.1143 0.059 Uiso 1 1 calc R . . C13 C 0.07492(12) 0.5068(5) 0.1333(2) 0.0322(10) Uani 1 1 d . . . C14 C 0.05139(13) 0.4702(5) 0.0618(2) 0.0431(11) Uani 1 1 d . . . H14 H 0.0369 0.3742 0.0481 0.052 Uiso 1 1 calc R . . C15 C 0.04961(15) 0.5782(7) 0.0109(2) 0.0583(14) Uani 1 1 d . . . H15 H 0.0336 0.5544 -0.0372 0.070 Uiso 1 1 calc R . . C16 C 0.07082(17) 0.7185(6) 0.0301(3) 0.0601(15) Uani 1 1 d . . . H16 H 0.0695 0.7888 -0.0048 0.072 Uiso 1 1 calc R . . C17 C 0.09404(15) 0.7563(5) 0.1007(3) 0.0532(13) Uani 1 1 d . . . H17 H 0.1084 0.8524 0.1137 0.064 Uiso 1 1 calc R . . C18 C 0.09605(13) 0.6524(5) 0.1520(2) 0.0382(11) Uani 1 1 d . . . H18 H 0.1117 0.6791 0.2000 0.046 Uiso 1 1 calc R . . C19 C 0.13077(14) 0.2345(6) 0.1059(2) 0.0461(12) Uani 1 1 d . . . C20 C 0.15318(13) 0.3899(6) 0.1334(2) 0.0433(11) Uani 1 1 d . . . C21 C 0.16179(16) 0.4903(7) 0.0935(3) 0.0637(15) Uani 1 1 d . . . H21 H 0.1535 0.4638 0.0462 0.076 Uiso 1 1 calc R . . C22 C 0.18297(18) 0.6323(7) 0.1239(4) 0.0786(18) Uani 1 1 d . . . H22 H 0.1886 0.7041 0.0974 0.094 Uiso 1 1 calc R . . C23 C 0.19530(17) 0.6635(7) 0.1946(4) 0.0765(18) Uani 1 1 d . . . H23 H 0.2099 0.7565 0.2166 0.092 Uiso 1 1 calc R . . C24 C 0.18617(15) 0.5589(6) 0.2323(3) 0.0588(14) Uani 1 1 d . . . H24 H 0.1951 0.5813 0.2802 0.071 Uiso 1 1 calc R . . C25 C 0.18194(12) 0.4626(5) 0.3921(2) 0.0381(11) Uani 1 1 d . . . C26 C 0.20750(13) 0.3951(5) 0.4571(2) 0.0478(12) Uani 1 1 d . . . H26 H 0.2141 0.2842 0.4603 0.057 Uiso 1 1 calc R . . C27 C 0.22330(15) 0.4916(6) 0.5174(2) 0.0583(14) Uani 1 1 d . . . H27 H 0.2409 0.4452 0.5610 0.070 Uiso 1 1 calc R . . C28 C 0.21358(14) 0.6578(6) 0.5145(2) 0.0503(13) Uani 1 1 d . . . C29 C 0.18765(16) 0.7202(5) 0.4486(3) 0.0619(16) Uani 1 1 d . . . H29 H 0.1807 0.8307 0.4452 0.074 Uiso 1 1 calc R . . C30 C 0.17153(15) 0.6263(5) 0.3875(2) 0.0601(15) Uani 1 1 d . . . H30 H 0.1539 0.6723 0.3438 0.072 Uiso 1 1 calc R . . C31 C 0.23059(18) 0.7627(6) 0.5812(3) 0.0771(18) Uani 1 1 d . . . H31A H 0.2118 0.7843 0.5938 0.116 Uiso 1 1 calc R . . H31B H 0.2392 0.8654 0.5725 0.116 Uiso 1 1 calc R . . H31C H 0.2515 0.7052 0.6196 0.116 Uiso 1 1 calc R . . O99 O 0.1252(3) 0.0688(8) 0.4603(4) 0.239(4) Uani 1 1 d G . . H99A H 0.1209 0.0273 0.4211 0.359 Uiso 1 1 d R . . H99B H 0.1088 0.1430 0.4521 0.359 Uiso 1 1 d 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 0.04195(12) 0.03075(9) 0.02743(10) -0.00126(7) 0.00828(8) 0.00805(8) N1 0.034(2) 0.042(2) 0.045(2) -0.0045(17) 0.0185(19) 0.0057(17) N2 0.043(2) 0.037(2) 0.0275(19) 0.0037(15) 0.0076(17) 0.0079(17) O1 0.047(2) 0.0372(16) 0.0297(16) -0.0050(13) 0.0167(15) 0.0027(14) O2 0.114(4) 0.076(2) 0.046(2) -0.0185(19) 0.046(2) -0.011(2) P1 0.0392(7) 0.0279(5) 0.0271(6) 0.0001(4) 0.0163(5) 0.0011(5) Br1 0.0618(4) 0.0883(4) 0.0708(4) -0.0045(3) 0.0121(3) 0.0414(3) Br2 0.1111(5) 0.0310(2) 0.0517(3) 0.0095(2) 0.0319(3) 0.0034(3) C1 0.048(3) 0.029(2) 0.035(2) -0.0052(18) 0.026(2) -0.0015(19) C2 0.067(4) 0.044(3) 0.039(3) -0.003(2) 0.033(3) -0.004(2) C3 0.089(5) 0.065(4) 0.048(3) -0.003(3) 0.045(3) -0.004(3) C4 0.123(6) 0.079(4) 0.073(4) -0.020(3) 0.074(4) -0.001(4) C5 0.118(6) 0.051(3) 0.088(5) -0.005(3) 0.073(4) 0.020(3) C6 0.078(4) 0.046(3) 0.063(3) -0.009(2) 0.050(3) 0.005(3) C7 0.040(3) 0.034(2) 0.034(2) 0.0031(17) 0.018(2) 0.0010(19) C8 0.055(3) 0.051(3) 0.046(3) -0.003(2) 0.027(3) -0.007(3) C9 0.055(4) 0.077(4) 0.065(3) 0.001(3) 0.037(3) -0.016(3) C10 0.060(4) 0.054(3) 0.064(3) -0.002(3) 0.028(3) -0.020(3) C11 0.062(4) 0.046(3) 0.069(4) -0.014(2) 0.030(3) -0.017(3) C12 0.046(3) 0.042(3) 0.062(3) -0.011(2) 0.029(3) -0.005(2) C13 0.032(3) 0.035(2) 0.032(2) 0.0038(18) 0.018(2) 0.0070(19) C14 0.037(3) 0.053(3) 0.035(3) 0.003(2) 0.016(2) 0.003(2) C15 0.058(4) 0.086(4) 0.029(3) 0.015(3) 0.021(3) 0.018(3) C16 0.082(4) 0.056(3) 0.061(4) 0.029(3) 0.051(3) 0.021(3) C17 0.074(4) 0.033(2) 0.070(4) 0.011(2) 0.049(3) 0.009(2) C18 0.047(3) 0.031(2) 0.040(3) 0.0015(19) 0.025(2) 0.007(2) C19 0.049(3) 0.048(3) 0.039(3) -0.006(2) 0.022(2) 0.009(2) C20 0.042(3) 0.053(3) 0.041(3) -0.005(2) 0.026(2) 0.006(2) C21 0.073(4) 0.071(4) 0.067(4) -0.006(3) 0.050(3) 0.002(3) C22 0.089(5) 0.073(4) 0.109(5) 0.004(4) 0.076(5) -0.006(3) C23 0.080(5) 0.063(4) 0.111(5) -0.024(4) 0.066(4) -0.025(3) C24 0.055(4) 0.054(3) 0.069(4) -0.018(3) 0.033(3) -0.015(3) C25 0.037(3) 0.042(2) 0.029(2) -0.0062(18) 0.013(2) 0.000(2) C26 0.056(3) 0.044(3) 0.032(2) 0.001(2) 0.015(2) 0.010(2) C27 0.063(4) 0.071(3) 0.028(3) 0.001(2) 0.013(3) 0.004(3) C28 0.053(3) 0.056(3) 0.041(3) -0.012(2) 0.024(3) -0.011(2) C29 0.066(4) 0.038(3) 0.061(3) -0.014(2) 0.018(3) 0.004(2) C30 0.067(4) 0.039(3) 0.041(3) -0.006(2) 0.003(3) 0.004(2) C31 0.095(5) 0.079(4) 0.054(3) -0.031(3) 0.036(3) -0.030(3) O99 0.431(14) 0.142(5) 0.241(8) 0.076(5) 0.241(9) 0.099(7) _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 N2 1.717(3) . ? Re1 O1 2.057(3) . ? Re1 N1 2.113(4) . ? Re1 P1 2.4444(11) . ? Re1 Br2 2.5120(6) . ? Re1 Br1 2.5490(6) . ? N1 C24 1.352(6) . ? N1 C20 1.358(5) . ? N2 C25 1.385(5) . ? O1 C19 1.293(5) . ? O2 C19 1.215(5) . ? P1 C1 1.819(4) . ? P1 C13 1.821(4) . ? P1 C7 1.837(4) . ? C1 C6 1.369(6) . ? C1 C2 1.396(5) . ? C2 C3 1.365(6) . ? C2 H2 0.9300 . ? C3 C4 1.368(7) . ? C3 H3 0.9300 . ? C4 C5 1.372(7) . ? C4 H4 0.9300 . ? C5 C6 1.392(7) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.378(6) . ? C7 C8 1.379(6) . ? C8 C9 1.380(6) . ? C8 H8 0.9300 . ? C9 C10 1.367(7) . ? C9 H9 0.9300 . ? C10 C11 1.368(7) . ? C10 H10 0.9300 . ? C11 C12 1.384(6) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.382(5) . ? C13 C18 1.396(6) . ? C14 C15 1.385(6) . ? C14 H14 0.9300 . ? C15 C16 1.361(7) . ? C15 H15 0.9300 . ? C16 C17 1.367(7) . ? C16 H16 0.9300 . ? C17 C18 1.369(6) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.492(6) . ? C20 C21 1.363(7) . ? C21 C22 1.389(7) . ? C21 H21 0.9300 . ? C22 C23 1.377(8) . ? C22 H22 0.9300 . ? C23 C24 1.361(7) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C26 1.375(6) . ? C25 C30 1.380(6) . ? C26 C27 1.372(6) . ? C26 H26 0.9300 . ? C27 C28 1.395(6) . ? C27 H27 0.9300 . ? C28 C29 1.375(6) . ? C28 C31 1.511(6) . ? C29 C30 1.373(6) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? O99 H99A 0.8499 . ? O99 H99B 0.8499 . ? 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 N2 Re1 O1 168.39(13) . . ? N2 Re1 N1 94.76(15) . . ? O1 Re1 N1 75.46(13) . . ? N2 Re1 P1 93.98(12) . . ? O1 Re1 P1 80.80(9) . . ? N1 Re1 P1 94.51(10) . . ? N2 Re1 Br2 99.49(12) . . ? O1 Re1 Br2 90.76(8) . . ? N1 Re1 Br2 165.23(10) . . ? P1 Re1 Br2 88.38(3) . . ? N2 Re1 Br1 98.95(12) . . ? O1 Re1 Br1 86.37(8) . . ? N1 Re1 Br1 83.80(9) . . ? P1 Re1 Br1 167.06(3) . . ? Br2 Re1 Br1 90.14(2) . . ? C24 N1 C20 117.6(4) . . ? C24 N1 Re1 126.2(3) . . ? C20 N1 Re1 116.2(3) . . ? C25 N2 Re1 175.1(3) . . ? C19 O1 Re1 121.1(3) . . ? C1 P1 C13 106.71(18) . . ? C1 P1 C7 103.8(2) . . ? C13 P1 C7 106.17(19) . . ? C1 P1 Re1 112.37(15) . . ? C13 P1 Re1 109.52(14) . . ? C7 P1 Re1 117.59(14) . . ? C6 C1 C2 119.1(4) . . ? C6 C1 P1 123.9(3) . . ? C2 C1 P1 117.0(3) . . ? C3 C2 C1 121.0(4) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 119.2(5) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C3 C4 C5 121.1(5) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C4 C5 C6 119.6(5) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C1 C6 C5 119.9(5) . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C12 C7 C8 118.8(4) . . ? C12 C7 P1 120.8(4) . . ? C8 C7 P1 120.3(3) . . ? C7 C8 C9 120.6(5) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C10 C9 C8 119.9(5) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 120.2(5) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C10 C11 C12 120.1(5) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C7 C12 C11 120.4(5) . . ? C7 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 C18 118.9(4) . . ? C14 C13 P1 122.7(3) . . ? C18 C13 P1 117.9(3) . . ? C13 C14 C15 119.2(4) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C16 C15 C14 121.2(5) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C17 120.1(4) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C18 119.9(5) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C17 C18 C13 120.8(4) . . ? C17 C18 H18 119.6 . . ? C13 C18 H18 119.6 . . ? O2 C19 O1 125.1(5) . . ? O2 C19 C20 121.6(5) . . ? O1 C19 C20 113.3(4) . . ? N1 C20 C21 122.4(4) . . ? N1 C20 C19 113.8(4) . . ? C21 C20 C19 123.7(4) . . ? C20 C21 C22 119.6(5) . . ? C20 C21 H21 120.2 . . ? C22 C21 H21 120.2 . . ? C23 C22 C21 117.9(6) . . ? C23 C22 H22 121.0 . . ? C21 C22 H22 121.0 . . ? C24 C23 C22 120.3(5) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? N1 C24 C23 122.2(5) . . ? N1 C24 H24 118.9 . . ? C23 C24 H24 118.9 . . ? C26 C25 C30 120.1(4) . . ? C26 C25 N2 118.9(4) . . ? C30 C25 N2 120.9(4) . . ? C27 C26 C25 119.9(4) . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C26 C27 C28 121.4(4) . . ? C26 C27 H27 119.3 . . ? C28 C27 H27 119.3 . . ? C29 C28 C27 116.9(4) . . ? C29 C28 C31 121.9(5) . . ? C27 C28 C31 121.1(5) . . ? C30 C29 C28 122.8(4) . . ? C30 C29 H29 118.6 . . ? C28 C29 H29 118.6 . . ? C29 C30 C25 118.9(4) . . ? C29 C30 H30 120.6 . . ? C25 C30 H30 120.6 . . ? C28 C31 H31A 109.5 . . ? C28 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C28 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? H99A O99 H99B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.747 _refine_diff_density_min -0.873 _refine_diff_density_rms 0.081 _database_code_depnum_ccdc_archive 'CCDC 899357' ####################################################################### # # 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_ren370a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H26 Cl2 N2 O2 P Re' _chemical_formula_sum 'C31 H26 Cl2 N2 O2 P Re' _chemical_formula_weight 746.61 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' 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 Cc 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' _cell_length_a 15.5583(7) _cell_length_b 14.0916(8) _cell_length_c 13.5172(7) _cell_angle_alpha 90.00 _cell_angle_beta 97.838(4) _cell_angle_gamma 90.00 _cell_volume 2935.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2860 _cell_measurement_theta_min 4.3290 _cell_measurement_theta_max 28.9270 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.33751 _exptl_crystal_size_mid 0.16123 _exptl_crystal_size_min 0.09174 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.689 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1464 _exptl_absorpt_coefficient_mu 4.407 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details ;CrysAlis RED, (2005) ; _exptl_absorpt_correction_T_min 0.60811 _exptl_absorpt_correction_T_max 1.00000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6955 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_unetI/netI 0.0446 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4158 _reflns_number_gt 3849 _reflns_threshold_expression >2sigma(I) #========================================================================== # # REFINEMENT DATA _computing_data_collection 'CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000)' _computing_cell_refinement 'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)' _computing_data_reduction 'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;XP in SHELXTL/PC (Sheldrick, 1990b) ORTEP-3 W v. 1.062 (Farrugia 1997) ; _computing_publication_material ;SHELXL-97 (Sheldrick, 1997) and PLATON (Spek, 1990) ; _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^)+(0.0543P)^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 -0.013(10) _refine_ls_number_reflns 4158 _refine_ls_number_parameters 353 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0332 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_ref 0.0955 _refine_ls_wR_factor_gt 0.0911 _refine_ls_goodness_of_fit_ref 1.164 _refine_ls_restrained_S_all 1.163 _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 0.000520(11) 0.32400(2) 0.249610(11) 0.03580(13) Uani 1 1 d . . . N1 N -0.0923(5) 0.4087(6) 0.1555(5) 0.0371(18) Uani 1 1 d . . . N2 N 0.0797(9) 0.3356(8) 0.1808(12) 0.053(4) Uani 1 1 d . . . O1 O -0.1038(7) 0.3257(4) 0.3245(7) 0.033(2) Uani 1 1 d . . . O2 O -0.2393(4) 0.3832(5) 0.3259(5) 0.0482(17) Uani 1 1 d . . . P1 P 0.09070(17) 0.23135(18) 0.3776(2) 0.0367(6) Uani 1 1 d . . . Cl1 Cl -0.0702(2) 0.1904(2) 0.1651(3) 0.0610(8) Uani 1 1 d . . . Cl2 Cl 0.03675(18) 0.46616(18) 0.34462(19) 0.0495(6) Uani 1 1 d . . . C1 C 0.0691(6) 0.1049(7) 0.3899(8) 0.045(2) Uani 1 1 d . . . C2 C 0.0571(7) 0.0670(8) 0.4820(9) 0.062(3) Uani 1 1 d . . . H2 H 0.0604 0.1049 0.5387 0.074 Uiso 1 1 calc R . . C3 C 0.0398(9) -0.0315(11) 0.4865(14) 0.083(4) Uani 1 1 d . . . H3 H 0.0296 -0.0583 0.5467 0.099 Uiso 1 1 calc R . . C4 C 0.0378(9) -0.0861(10) 0.4065(16) 0.092(6) Uani 1 1 d . . . H4 H 0.0283 -0.1508 0.4125 0.111 Uiso 1 1 calc R . . C5 C 0.0495(8) -0.0493(8) 0.3138(14) 0.077(4) Uani 1 1 d . . . H5 H 0.0475 -0.0886 0.2583 0.092 Uiso 1 1 calc R . . C6 C 0.0640(8) 0.0459(8) 0.3060(10) 0.061(3) Uani 1 1 d . . . H6 H 0.0706 0.0718 0.2442 0.074 Uiso 1 1 calc R . . C7 C 0.0991(7) 0.2763(7) 0.5052(7) 0.044(2) Uani 1 1 d . . . C8 C 0.1726(9) 0.2727(8) 0.5689(8) 0.060(3) Uani 1 1 d . . . H8 H 0.2228 0.2515 0.5456 0.072 Uiso 1 1 calc R . . C9 C 0.1773(13) 0.2990(10) 0.6680(11) 0.070(5) Uani 1 1 d . . . H9 H 0.2297 0.2980 0.7105 0.084 Uiso 1 1 calc R . . C10 C 0.1002(12) 0.3270(8) 0.7019(9) 0.066(4) Uani 1 1 d . . . H10 H 0.1006 0.3445 0.7683 0.079 Uiso 1 1 calc R . . C11 C 0.0245(11) 0.3289(9) 0.6384(10) 0.073(4) Uani 1 1 d . . . H11 H -0.0266 0.3468 0.6619 0.087 Uiso 1 1 calc R . . C12 C 0.0231(7) 0.3049(8) 0.5407(8) 0.051(3) Uani 1 1 d . . . H12 H -0.0288 0.3074 0.4975 0.061 Uiso 1 1 calc R . . C13 C 0.2008(7) 0.2348(7) 0.3503(7) 0.044(2) Uani 1 1 d . . . C14 C 0.2453(8) 0.3221(8) 0.3443(10) 0.057(3) Uani 1 1 d . . . H14 H 0.2174 0.3764 0.3627 0.068 Uiso 1 1 calc R . . C15 C 0.3194(12) 0.3338(9) 0.3164(13) 0.082(5) Uani 1 1 d . . . H15 H 0.3379 0.3942 0.3009 0.099 Uiso 1 1 calc R . . C16 C 0.3749(8) 0.2522(10) 0.3089(11) 0.073(4) Uani 1 1 d . . . H16 H 0.4328 0.2577 0.2994 0.088 Uiso 1 1 calc R . . C17 C 0.3334(10) 0.1622(10) 0.3171(15) 0.072(5) Uani 1 1 d . . . H17 H 0.3639 0.1070 0.3072 0.086 Uiso 1 1 calc R . . C18 C 0.2500(8) 0.1550(8) 0.3393(10) 0.052(3) Uani 1 1 d . . . H18 H 0.2264 0.0953 0.3470 0.062 Uiso 1 1 calc R . . C19 C -0.1764(6) 0.3717(7) 0.2854(6) 0.032(2) Uani 1 1 d . . . C20 C -0.1684(7) 0.4190(7) 0.1884(6) 0.040(2) Uani 1 1 d . . . C21 C -0.2324(6) 0.4733(7) 0.1360(7) 0.044(2) Uani 1 1 d . . . H21 H -0.2854 0.4810 0.1596 0.053 Uiso 1 1 calc R . . C22 C -0.2180(8) 0.5160(9) 0.0489(8) 0.059(3) Uani 1 1 d . . . H22 H -0.2613 0.5520 0.0122 0.071 Uiso 1 1 calc R . . C23 C -0.1405(9) 0.5053(9) 0.0175(9) 0.067(3) Uani 1 1 d . . . H23 H -0.1290 0.5357 -0.0403 0.081 Uiso 1 1 calc R . . C24 C -0.0784(7) 0.4495(9) 0.0703(7) 0.054(3) Uani 1 1 d . . . H24 H -0.0257 0.4401 0.0464 0.065 Uiso 1 1 calc R . . C25 C 0.1409(7) 0.3549(8) 0.1123(8) 0.045(2) Uani 1 1 d . . . C26 C 0.1739(10) 0.4422(8) 0.1036(9) 0.068(4) Uani 1 1 d . . . H26 H 0.1550 0.4927 0.1394 0.082 Uiso 1 1 calc R . . C27 C 0.2353(8) 0.4566(8) 0.0424(9) 0.059(3) Uani 1 1 d . . . H27 H 0.2626 0.5153 0.0436 0.071 Uiso 1 1 calc R . . C28 C 0.2586(7) 0.3873(7) -0.0218(8) 0.050(3) Uani 1 1 d . . . C29 C 0.2193(8) 0.2975(9) -0.0136(9) 0.060(3) Uani 1 1 d . . . H29 H 0.2295 0.2502 -0.0585 0.072 Uiso 1 1 calc R . . C30 C 0.1695(8) 0.2778(8) 0.0539(8) 0.054(3) Uani 1 1 d . . . H30 H 0.1527 0.2157 0.0643 0.065 Uiso 1 1 calc R . . C31 C 0.3218(11) 0.4056(11) -0.0927(11) 0.086(5) Uani 1 1 d . . . H31A H 0.2911 0.4217 -0.1570 0.129 Uiso 1 1 calc R . . H31B H 0.3560 0.3496 -0.0985 0.129 Uiso 1 1 calc R . . H31C H 0.3591 0.4572 -0.0684 0.129 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 0.03221(19) 0.04295(19) 0.03349(18) 0.0050(2) 0.00895(12) 0.0050(3) N1 0.029(4) 0.045(5) 0.038(4) 0.006(3) 0.008(3) 0.000(4) N2 0.030(7) 0.064(7) 0.061(8) -0.002(5) -0.006(5) 0.015(4) O1 0.041(6) 0.038(4) 0.024(4) 0.006(2) 0.021(4) 0.003(3) O2 0.036(4) 0.064(5) 0.046(4) 0.000(3) 0.012(3) 0.011(4) P1 0.0355(14) 0.0359(13) 0.0397(14) 0.0037(11) 0.0081(11) 0.0052(11) Cl1 0.057(2) 0.0589(18) 0.066(2) -0.0146(14) 0.0032(15) 0.0061(14) Cl2 0.0546(16) 0.0415(13) 0.0528(15) 0.0016(11) 0.0094(12) 0.0009(13) C1 0.030(5) 0.046(6) 0.058(6) 0.015(5) -0.001(4) 0.010(4) C2 0.044(7) 0.061(7) 0.075(8) 0.028(6) -0.013(6) -0.014(6) C3 0.058(8) 0.063(8) 0.120(12) 0.043(9) -0.014(8) -0.008(7) C4 0.067(10) 0.042(8) 0.153(16) 0.023(9) -0.038(10) -0.010(7) C5 0.037(6) 0.038(6) 0.145(13) -0.010(8) -0.022(7) 0.000(5) C6 0.055(7) 0.054(7) 0.073(8) -0.003(6) -0.001(6) 0.012(6) C7 0.066(7) 0.037(5) 0.032(5) 0.011(4) 0.014(5) 0.008(5) C8 0.087(9) 0.048(6) 0.040(6) -0.002(5) -0.006(6) 0.029(6) C9 0.114(15) 0.044(7) 0.048(7) 0.005(6) -0.003(8) 0.006(9) C10 0.108(13) 0.053(7) 0.034(6) 0.001(5) -0.001(7) 0.008(7) C11 0.088(11) 0.084(10) 0.052(8) 0.016(6) 0.033(7) 0.033(7) C12 0.042(6) 0.071(7) 0.041(6) 0.013(5) 0.011(5) 0.015(5) C13 0.053(6) 0.043(6) 0.038(5) -0.002(4) 0.011(5) 0.005(5) C14 0.041(7) 0.057(7) 0.075(8) -0.012(5) 0.017(6) -0.011(5) C15 0.104(13) 0.047(7) 0.105(12) -0.016(7) 0.048(10) -0.025(7) C16 0.026(6) 0.083(9) 0.112(11) -0.030(8) 0.017(6) -0.008(6) C17 0.031(7) 0.068(9) 0.119(14) -0.030(9) 0.015(8) 0.006(7) C18 0.043(7) 0.039(6) 0.076(8) -0.001(5) 0.018(6) 0.004(5) C19 0.023(5) 0.040(5) 0.034(5) -0.005(4) 0.002(4) -0.001(4) C20 0.051(6) 0.038(5) 0.028(4) -0.008(4) -0.003(4) -0.005(5) C21 0.031(5) 0.050(6) 0.049(6) 0.000(5) -0.003(4) 0.004(5) C22 0.055(8) 0.057(7) 0.058(7) 0.015(5) -0.014(6) 0.005(6) C23 0.076(9) 0.072(8) 0.054(7) 0.033(6) 0.012(6) 0.010(7) C24 0.034(6) 0.087(9) 0.041(6) 0.023(5) -0.002(4) 0.005(5) C25 0.050(6) 0.048(6) 0.039(5) -0.005(5) 0.011(5) -0.001(5) C26 0.107(11) 0.035(6) 0.074(8) 0.000(5) 0.049(8) 0.003(6) C27 0.055(7) 0.039(6) 0.091(9) -0.003(6) 0.036(6) -0.008(5) C28 0.051(6) 0.043(6) 0.059(7) 0.002(5) 0.021(5) 0.001(5) C29 0.052(7) 0.064(7) 0.067(8) -0.018(6) 0.022(6) 0.005(6) C30 0.057(7) 0.047(6) 0.062(7) -0.011(5) 0.024(6) -0.011(5) C31 0.109(12) 0.079(10) 0.084(10) -0.011(8) 0.064(9) -0.015(9) _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 N2 1.650(17) . ? Re1 O1 2.027(10) . ? Re1 N1 2.151(7) . ? Re1 Cl1 2.391(3) . ? Re1 Cl2 2.405(3) . ? Re1 P1 2.450(2) . ? N1 C20 1.328(13) . ? N1 C24 1.332(12) . ? N2 C25 1.441(19) . ? O1 C19 1.345(13) . ? O2 C19 1.196(11) . ? P1 C13 1.801(11) . ? P1 C1 1.825(11) . ? P1 C7 1.826(10) . ? C1 C2 1.391(15) . ? C1 C6 1.400(16) . ? C2 C3 1.417(17) . ? C2 H2 0.9300 . ? C3 C4 1.32(2) . ? C3 H3 0.9300 . ? C4 C5 1.39(2) . ? C4 H4 0.9300 . ? C5 C6 1.366(16) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.336(15) . ? C7 C12 1.395(15) . ? C8 C9 1.382(18) . ? C8 H8 0.9300 . ? C9 C10 1.40(2) . ? C9 H9 0.9300 . ? C10 C11 1.36(2) . ? C10 H10 0.9300 . ? C11 C12 1.360(18) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C18 1.381(15) . ? C13 C14 1.420(15) . ? C14 C15 1.27(2) . ? C14 H14 0.9300 . ? C15 C16 1.45(2) . ? C15 H15 0.9300 . ? C16 C17 1.434(19) . ? C16 H16 0.9300 . ? C17 C18 1.37(2) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.492(13) . ? C20 C21 1.374(14) . ? C21 C22 1.367(15) . ? C21 H21 0.9300 . ? C22 C23 1.341(17) . ? C22 H22 0.9300 . ? C23 C24 1.368(16) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C26 1.345(16) . ? C25 C30 1.448(16) . ? C26 C27 1.361(16) . ? C26 H26 0.9300 . ? C27 C28 1.386(15) . ? C27 H27 0.9300 . ? C28 C29 1.417(17) . ? C28 C31 1.486(16) . ? C29 C30 1.305(17) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Re1 O1 172.2(5) . . ? N2 Re1 N1 96.0(5) . . ? O1 Re1 N1 76.7(3) . . ? N2 Re1 Cl1 98.0(4) . . ? O1 Re1 Cl1 84.3(2) . . ? N1 Re1 Cl1 85.7(2) . . ? N2 Re1 Cl2 94.6(4) . . ? O1 Re1 Cl2 82.5(2) . . ? N1 Re1 Cl2 86.8(2) . . ? Cl1 Re1 Cl2 165.95(10) . . ? N2 Re1 P1 92.9(5) . . ? O1 Re1 P1 94.3(3) . . ? N1 Re1 P1 170.7(2) . . ? Cl1 Re1 P1 95.72(12) . . ? Cl2 Re1 P1 89.83(9) . . ? C20 N1 C24 120.0(8) . . ? C20 N1 Re1 114.8(6) . . ? C24 N1 Re1 125.2(7) . . ? C25 N2 Re1 171.9(10) . . ? C19 O1 Re1 119.8(7) . . ? C13 P1 C1 103.7(5) . . ? C13 P1 C7 103.7(5) . . ? C1 P1 C7 104.0(5) . . ? C13 P1 Re1 108.1(3) . . ? C1 P1 Re1 119.4(3) . . ? C7 P1 Re1 116.3(3) . . ? C2 C1 C6 119.8(11) . . ? C2 C1 P1 120.4(9) . . ? C6 C1 P1 119.8(8) . . ? C1 C2 C3 117.7(13) . . ? C1 C2 H2 121.2 . . ? C3 C2 H2 121.2 . . ? C4 C3 C2 121.2(14) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 121.9(13) . . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.1 . . ? C6 C5 C4 118.6(14) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C5 C6 C1 120.8(13) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? C8 C7 C12 118.7(10) . . ? C8 C7 P1 122.7(9) . . ? C12 C7 P1 118.1(8) . . ? C7 C8 C9 122.8(14) . . ? C7 C8 H8 118.6 . . ? C9 C8 H8 118.6 . . ? C8 C9 C10 117.3(15) . . ? C8 C9 H9 121.4 . . ? C10 C9 H9 121.4 . . ? C11 C10 C9 120.5(13) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 120.4(14) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C7 120.2(11) . . ? C11 C12 H12 119.9 . . ? C7 C12 H12 119.9 . . ? C18 C13 C14 114.6(11) . . ? C18 C13 P1 123.9(9) . . ? C14 C13 P1 121.4(8) . . ? C15 C14 C13 126.8(12) . . ? C15 C14 H14 116.6 . . ? C13 C14 H14 116.6 . . ? C14 C15 C16 119.3(12) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C17 C16 C15 114.7(12) . . ? C17 C16 H16 122.6 . . ? C15 C16 H16 122.6 . . ? C18 C17 C16 122.0(12) . . ? C18 C17 H17 119.0 . . ? C16 C17 H17 119.0 . . ? C17 C18 C13 121.2(12) . . ? C17 C18 H18 119.4 . . ? C13 C18 H18 119.4 . . ? O2 C19 O1 125.5(9) . . ? O2 C19 C20 120.9(9) . . ? O1 C19 C20 113.2(8) . . ? N1 C20 C21 120.3(9) . . ? N1 C20 C19 115.5(8) . . ? C21 C20 C19 124.1(9) . . ? C22 C21 C20 119.8(10) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C23 C22 C21 118.9(10) . . ? C23 C22 H22 120.6 . . ? C21 C22 H22 120.6 . . ? C22 C23 C24 120.1(11) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? N1 C24 C23 120.8(11) . . ? N1 C24 H24 119.6 . . ? C23 C24 H24 119.6 . . ? C26 C25 N2 121.5(10) . . ? C26 C25 C30 119.3(11) . . ? N2 C25 C30 119.1(10) . . ? C25 C26 C27 119.8(11) . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.1 . . ? C26 C27 C28 122.8(10) . . ? C26 C27 H27 118.6 . . ? C28 C27 H27 118.6 . . ? C27 C28 C29 115.3(11) . . ? C27 C28 C31 122.3(10) . . ? C29 C28 C31 122.4(10) . . ? C30 C29 C28 123.3(11) . . ? C30 C29 H29 118.4 . . ? C28 C29 H29 118.4 . . ? C29 C30 C25 118.5(11) . . ? C29 C30 H30 120.7 . . ? C25 C30 H30 120.7 . . ? C28 C31 H31A 109.5 . . ? C28 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C28 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C12 H12 O1 0.93 2.48 3.310(15) 148.5 . C23 H23 O2 0.93 2.58 3.233(13) 127.3 2_564 C29 H29 O2 0.93 2.53 3.462(14) 177.3 4_554 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.519 _refine_diff_density_min -0.423 _refine_diff_density_rms 0.088 _database_code_depnum_ccdc_archive 'CCDC 936243' ####################################################################### # # 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_ren371 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H40 Cl2 N O P2 Re' _chemical_formula_sum 'C44 H40 Cl2 N O P2 Re' _chemical_formula_weight 917.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' 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' O O 0.0106 0.0060 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.2167(3) _cell_length_b 13.6809(4) _cell_length_c 14.3814(4) _cell_angle_alpha 96.458(3) _cell_angle_beta 92.186(2) _cell_angle_gamma 98.091(3) _cell_volume 1974.52(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8093 _cell_measurement_theta_min 3.6070 _cell_measurement_theta_max 28.0310 _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.14202 _exptl_crystal_size_mid 0.07555 _exptl_crystal_size_min 0.04778 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 916 _exptl_absorpt_coefficient_mu 3.328 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details ;CrysAlis RED, (2005) ; _exptl_absorpt_correction_T_min 0.70916 _exptl_absorpt_correction_T_max 1.00000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15600 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_unetI/netI 0.0498 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6924 _reflns_number_gt 6017 _reflns_threshold_expression >2sigma(I) #========================================================================== # # REFINEMENT DATA _computing_data_collection 'CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000)' _computing_cell_refinement 'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)' _computing_data_reduction 'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;XP in SHELXTL/PC (Sheldrick, 1990b) ORTEP-3 W v. 1.062 (Farrugia 1997) ; _computing_publication_material ;SHELXL-97 (Sheldrick, 1997) and PLATON (Spek, 1990) ; _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^)+(0.0252P)^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 6924 _refine_ls_number_parameters 462 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0607 _refine_ls_wR_factor_gt 0.0583 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _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 0.700330(15) 0.703429(11) 0.707807(9) 0.03224(6) Uani 1 1 d . . . N2 N 0.8538(3) 0.7783(2) 0.73194(19) 0.0358(7) Uani 1 1 d . . . O1 O 0.5248(3) 0.6310(2) 0.69648(17) 0.0438(7) Uani 1 1 d . . . Cl1 Cl 0.62747(12) 0.77405(9) 0.85831(7) 0.0610(3) Uani 1 1 d . . . Cl2 Cl 0.73013(11) 0.61484(8) 0.55811(6) 0.0479(3) Uani 1 1 d . . . P1 P 0.62099(9) 0.83012(7) 0.61636(6) 0.0322(2) Uani 1 1 d . . . P2 P 0.78433(10) 0.57212(8) 0.79114(6) 0.0364(2) Uani 1 1 d . . . C1 C 0.7093(4) 0.8491(3) 0.5099(2) 0.0350(9) Uani 1 1 d . . . C2 C 0.6428(4) 0.8627(3) 0.4267(3) 0.0457(10) Uani 1 1 d . . . H2 H 0.5509 0.8566 0.4228 0.055 Uiso 1 1 calc R . . C3 C 0.7142(5) 0.8854(4) 0.3500(3) 0.0542(12) Uani 1 1 d . . . H3 H 0.6694 0.8945 0.2948 0.065 Uiso 1 1 calc R . . C4 C 0.8489(5) 0.8945(3) 0.3541(3) 0.0540(12) Uani 1 1 d . . . H4 H 0.8957 0.9101 0.3022 0.065 Uiso 1 1 calc R . . C5 C 0.9151(4) 0.8804(4) 0.4354(3) 0.0550(12) Uani 1 1 d . . . H5 H 1.0071 0.8873 0.4388 0.066 Uiso 1 1 calc R . . C6 C 0.8453(4) 0.8560(3) 0.5124(3) 0.0464(10) Uani 1 1 d . . . H6 H 0.8908 0.8441 0.5663 0.056 Uiso 1 1 calc R . . C7 C 0.4475(4) 0.7962(3) 0.5751(2) 0.0355(9) Uani 1 1 d . . . C8 C 0.3541(4) 0.8574(3) 0.5954(3) 0.0432(10) Uani 1 1 d . . . H8 H 0.3797 0.9202 0.6283 0.052 Uiso 1 1 calc R . . C9 C 0.2227(4) 0.8266(4) 0.5675(3) 0.0517(11) Uani 1 1 d . . . H9 H 0.1603 0.8685 0.5818 0.062 Uiso 1 1 calc R . . C10 C 0.1838(4) 0.7345(4) 0.5186(3) 0.0551(12) Uani 1 1 d . . . H10 H 0.0949 0.7133 0.5010 0.066 Uiso 1 1 calc R . . C11 C 0.2773(4) 0.6733(3) 0.4958(3) 0.0487(11) Uani 1 1 d . . . H11 H 0.2516 0.6116 0.4608 0.058 Uiso 1 1 calc R . . C12 C 0.4080(4) 0.7030(3) 0.5244(2) 0.0420(10) Uani 1 1 d . . . H12 H 0.4702 0.6609 0.5099 0.050 Uiso 1 1 calc R . . C13 C 0.6357(4) 0.9579(3) 0.6741(2) 0.0355(9) Uani 1 1 d . . . C14 C 0.5834(4) 0.9753(3) 0.7616(3) 0.0485(11) Uani 1 1 d . . . H14 H 0.5386 0.9226 0.7888 0.058 Uiso 1 1 calc R . . C15 C 0.5979(4) 1.0701(4) 0.8076(3) 0.0558(12) Uani 1 1 d . . . H15 H 0.5634 1.0808 0.8662 0.067 Uiso 1 1 calc R . . C16 C 0.6624(4) 1.1490(4) 0.7689(3) 0.0584(12) Uani 1 1 d . . . H16 H 0.6717 1.2128 0.8008 0.070 Uiso 1 1 calc R . . C17 C 0.7131(5) 1.1331(3) 0.6821(3) 0.0618(13) Uani 1 1 d . . . H17 H 0.7559 1.1862 0.6546 0.074 Uiso 1 1 calc R . . C18 C 0.7004(4) 1.0379(3) 0.6361(3) 0.0471(10) Uani 1 1 d . . . H18 H 0.7365 1.0275 0.5781 0.057 Uiso 1 1 calc R . . C19 C 0.8967(4) 0.4981(3) 0.7289(2) 0.0392(9) Uani 1 1 d . . . C20 C 0.9098(4) 0.4051(3) 0.7524(3) 0.0540(12) Uani 1 1 d . . . H20 H 0.8545 0.3774 0.7954 0.065 Uiso 1 1 calc R . . C21 C 1.0034(5) 0.3521(4) 0.7132(3) 0.0599(12) Uani 1 1 d . . . H21 H 1.0110 0.2894 0.7299 0.072 Uiso 1 1 calc R . . C22 C 1.0855(4) 0.3924(3) 0.6494(3) 0.0498(11) Uani 1 1 d . . . H22 H 1.1498 0.3575 0.6235 0.060 Uiso 1 1 calc R . . C23 C 1.0723(4) 0.4840(3) 0.6244(3) 0.0490(11) Uani 1 1 d . . . H23 H 1.1269 0.5106 0.5804 0.059 Uiso 1 1 calc R . . C24 C 0.9786(4) 0.5381(3) 0.6634(3) 0.0449(10) Uani 1 1 d . . . H24 H 0.9707 0.6004 0.6458 0.054 Uiso 1 1 calc R . . C25 C 0.8860(4) 0.6240(3) 0.8975(3) 0.0482(11) Uani 1 1 d . . . C26 C 1.0212(5) 0.6302(4) 0.9000(3) 0.0682(15) Uani 1 1 d . . . H26 H 1.0616 0.5996 0.8500 0.082 Uiso 1 1 calc R . . C27 C 1.0994(6) 0.6824(5) 0.9770(4) 0.093(2) Uani 1 1 d . . . H27 H 1.1912 0.6872 0.9777 0.111 Uiso 1 1 calc R . . C28 C 1.0401(8) 0.7259(5) 1.0508(4) 0.092(2) Uani 1 1 d . . . H28 H 1.0917 0.7616 1.1014 0.111 Uiso 1 1 calc R . . C29 C 0.9084(7) 0.7175(5) 1.0510(4) 0.096(2) Uani 1 1 d . . . H29 H 0.8691 0.7448 1.1032 0.115 Uiso 1 1 calc R . . C30 C 0.8290(5) 0.6686(4) 0.9742(3) 0.0716(15) Uani 1 1 d . . . H30 H 0.7375 0.6659 0.9743 0.086 Uiso 1 1 calc R . . C31 C 0.6547(4) 0.4782(3) 0.8220(3) 0.0484(11) Uani 1 1 d . . . C32 C 0.5675(5) 0.4312(4) 0.7500(4) 0.0651(13) Uani 1 1 d . . . H32 H 0.5769 0.4483 0.6896 0.078 Uiso 1 1 calc R . . C33 C 0.4662(6) 0.3588(4) 0.7675(5) 0.093(2) Uani 1 1 d . . . H33 H 0.4069 0.3274 0.7190 0.111 Uiso 1 1 calc R . . C34 C 0.4530(7) 0.3332(5) 0.8567(7) 0.111(3) Uani 1 1 d . . . H34 H 0.3839 0.2850 0.8684 0.133 Uiso 1 1 calc R . . C35 C 0.5403(8) 0.3777(5) 0.9282(5) 0.102(2) Uani 1 1 d . . . H35 H 0.5319 0.3585 0.9880 0.122 Uiso 1 1 calc R . . C36 C 0.6410(5) 0.4510(4) 0.9119(4) 0.0714(15) Uani 1 1 d . . . H36 H 0.6996 0.4822 0.9609 0.086 Uiso 1 1 calc R . . C37 C 0.9578(4) 0.8442(3) 0.7785(2) 0.0399(10) Uani 1 1 d . . . C38 C 0.9317(4) 0.9312(3) 0.8297(3) 0.0547(12) Uani 1 1 d . . . H38 H 0.8461 0.9469 0.8304 0.066 Uiso 1 1 calc R . . C39 C 1.0346(5) 0.9938(4) 0.8795(3) 0.0693(15) Uani 1 1 d . . . H39 H 1.0177 1.0520 0.9137 0.083 Uiso 1 1 calc R . . C40 C 1.1622(5) 0.9717(4) 0.8794(3) 0.0672(15) Uani 1 1 d . . . C41 C 1.1861(4) 0.8865(4) 0.8271(3) 0.0694(15) Uani 1 1 d . . . H41 H 1.2719 0.8710 0.8266 0.083 Uiso 1 1 calc R . . C42 C 1.0858(4) 0.8234(4) 0.7754(3) 0.0544(12) Uani 1 1 d . . . H42 H 1.1043 0.7671 0.7387 0.065 Uiso 1 1 calc R . . C43 C 1.2740(6) 1.0404(5) 0.9372(4) 0.112(3) Uani 1 1 d . . . H43A H 1.3181 1.0859 0.8984 0.168 Uiso 1 1 calc R . . H43B H 1.3361 1.0014 0.9608 0.168 Uiso 1 1 calc R . . H43C H 1.2381 1.0769 0.9887 0.168 Uiso 1 1 calc R . . C44 C 0.4041(4) 0.6222(4) 0.7392(4) 0.0736(15) Uani 1 1 d . . . H44A H 0.3417 0.5722 0.7027 0.110 Uiso 1 1 calc R . . H44B H 0.3710 0.6847 0.7435 0.110 Uiso 1 1 calc R . . H44C H 0.4165 0.6035 0.8010 0.110 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 0.03394(10) 0.02764(9) 0.03494(9) 0.00332(6) -0.00041(6) 0.00482(6) N2 0.044(2) 0.0267(18) 0.0373(16) 0.0070(13) 0.0021(13) 0.0063(15) O1 0.0388(16) 0.0386(17) 0.0537(15) 0.0154(13) -0.0010(12) -0.0020(13) Cl1 0.0768(8) 0.0616(8) 0.0468(6) 0.0020(5) 0.0092(5) 0.0192(6) Cl2 0.0647(7) 0.0414(6) 0.0390(5) -0.0014(4) -0.0003(4) 0.0187(5) P1 0.0292(5) 0.0286(5) 0.0389(5) 0.0049(4) 0.0002(4) 0.0048(4) P2 0.0375(6) 0.0341(6) 0.0389(5) 0.0087(4) 0.0032(4) 0.0060(5) C1 0.035(2) 0.030(2) 0.042(2) 0.0045(17) 0.0042(16) 0.0094(17) C2 0.045(3) 0.047(3) 0.046(2) 0.0086(19) -0.0037(18) 0.008(2) C3 0.067(3) 0.061(3) 0.039(2) 0.011(2) 0.002(2) 0.018(3) C4 0.066(3) 0.051(3) 0.050(2) 0.016(2) 0.021(2) 0.017(2) C5 0.043(3) 0.060(3) 0.066(3) 0.019(2) 0.010(2) 0.012(2) C6 0.037(2) 0.057(3) 0.050(2) 0.018(2) 0.0028(17) 0.013(2) C7 0.034(2) 0.035(2) 0.038(2) 0.0087(17) 0.0005(15) 0.0050(18) C8 0.038(2) 0.042(3) 0.049(2) 0.0041(19) -0.0009(17) 0.007(2) C9 0.036(3) 0.062(3) 0.059(3) 0.010(2) -0.0008(19) 0.013(2) C10 0.038(3) 0.066(3) 0.060(3) 0.013(2) -0.0067(19) -0.002(2) C11 0.051(3) 0.042(3) 0.048(2) 0.007(2) -0.0104(19) -0.007(2) C12 0.044(3) 0.035(2) 0.045(2) 0.0043(18) -0.0002(17) 0.0014(19) C13 0.030(2) 0.033(2) 0.044(2) 0.0065(17) -0.0021(16) 0.0074(18) C14 0.046(3) 0.043(3) 0.056(3) 0.002(2) 0.0087(19) 0.007(2) C15 0.057(3) 0.056(3) 0.056(3) -0.004(2) 0.008(2) 0.020(2) C16 0.055(3) 0.037(3) 0.079(3) -0.007(2) -0.011(2) 0.009(2) C17 0.079(4) 0.035(3) 0.069(3) 0.003(2) 0.002(2) 0.003(2) C18 0.057(3) 0.036(3) 0.048(2) 0.0073(19) 0.0042(19) 0.005(2) C19 0.035(2) 0.038(2) 0.046(2) 0.0116(18) 0.0011(16) 0.0051(19) C20 0.063(3) 0.046(3) 0.059(3) 0.022(2) 0.020(2) 0.016(2) C21 0.071(3) 0.045(3) 0.072(3) 0.018(2) 0.017(2) 0.024(3) C22 0.045(3) 0.055(3) 0.054(2) 0.006(2) 0.0078(19) 0.020(2) C23 0.045(3) 0.053(3) 0.050(2) 0.012(2) 0.0116(18) 0.006(2) C24 0.045(3) 0.040(3) 0.050(2) 0.0132(19) 0.0010(18) 0.002(2) C25 0.047(3) 0.053(3) 0.046(2) 0.017(2) -0.0068(18) 0.006(2) C26 0.054(3) 0.092(4) 0.056(3) 0.017(3) -0.011(2) 0.000(3) C27 0.061(4) 0.123(6) 0.091(4) 0.033(4) -0.026(3) -0.004(4) C28 0.113(6) 0.094(5) 0.063(4) 0.007(3) -0.037(3) 0.002(4) C29 0.105(5) 0.123(6) 0.053(3) -0.014(3) -0.023(3) 0.024(4) C30 0.077(4) 0.085(4) 0.054(3) 0.002(3) -0.009(2) 0.022(3) C31 0.045(3) 0.037(3) 0.067(3) 0.010(2) 0.016(2) 0.013(2) C32 0.056(3) 0.039(3) 0.098(4) 0.008(3) 0.011(3) 0.002(2) C33 0.063(4) 0.045(4) 0.166(7) -0.001(4) 0.008(4) 0.001(3) C34 0.085(5) 0.054(4) 0.197(8) 0.016(5) 0.076(5) 0.002(4) C35 0.122(6) 0.071(5) 0.123(5) 0.033(4) 0.080(5) 0.012(4) C36 0.082(4) 0.059(3) 0.080(3) 0.021(3) 0.037(3) 0.014(3) C37 0.040(2) 0.039(2) 0.039(2) 0.0091(18) -0.0025(16) -0.0017(19) C38 0.051(3) 0.044(3) 0.065(3) -0.002(2) -0.002(2) -0.002(2) C39 0.078(4) 0.058(3) 0.060(3) -0.013(2) 0.011(2) -0.015(3) C40 0.063(4) 0.077(4) 0.049(3) 0.003(3) 0.002(2) -0.028(3) C41 0.036(3) 0.092(4) 0.072(3) -0.002(3) -0.001(2) -0.008(3) C42 0.043(3) 0.062(3) 0.055(3) -0.005(2) 0.0043(19) 0.003(2) C43 0.091(5) 0.136(6) 0.080(4) -0.030(4) -0.005(3) -0.049(4) C44 0.037(3) 0.088(4) 0.097(4) 0.028(3) 0.008(2) -0.003(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 N2 1.747(3) . ? Re1 O1 1.915(3) . ? Re1 Cl2 2.4006(9) . ? Re1 Cl1 2.4550(10) . ? Re1 P1 2.4936(10) . ? Re1 P2 2.4979(11) . ? N2 C37 1.389(5) . ? O1 C44 1.395(5) . ? P1 C7 1.826(4) . ? P1 C1 1.831(4) . ? P1 C13 1.833(4) . ? P2 C31 1.816(4) . ? P2 C19 1.829(4) . ? P2 C25 1.831(4) . ? C1 C6 1.378(5) . ? C1 C2 1.398(5) . ? C2 C3 1.386(5) . ? C2 H2 0.9300 . ? C3 C4 1.363(6) . ? C3 H3 0.9300 . ? C4 C5 1.374(6) . ? C4 H4 0.9300 . ? C5 C6 1.387(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.374(5) . ? C7 C12 1.395(5) . ? C8 C9 1.380(5) . ? C8 H8 0.9300 . ? C9 C10 1.370(6) . ? C9 H9 0.9300 . ? C10 C11 1.382(6) . ? C10 H10 0.9300 . ? C11 C12 1.373(5) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C18 1.375(5) . ? C13 C14 1.395(5) . ? C14 C15 1.374(6) . ? C14 H14 0.9300 . ? C15 C16 1.369(6) . ? C15 H15 0.9300 . ? C16 C17 1.375(6) . ? C16 H16 0.9300 . ? C17 C18 1.379(6) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.375(6) . ? C19 C24 1.391(5) . ? C20 C21 1.379(6) . ? C20 H20 0.9300 . ? C21 C22 1.376(6) . ? C21 H21 0.9300 . ? C22 C23 1.365(6) . ? C22 H22 0.9300 . ? C23 C24 1.387(6) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C26 1.371(6) . ? C25 C30 1.388(6) . ? C26 C27 1.404(7) . ? C26 H26 0.9300 . ? C27 C28 1.363(8) . ? C27 H27 0.9300 . ? C28 C29 1.334(8) . ? C28 H28 0.9300 . ? C29 C30 1.392(7) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 C32 1.378(6) . ? C31 C36 1.392(6) . ? C32 C33 1.379(7) . ? C32 H32 0.9300 . ? C33 C34 1.375(9) . ? C33 H33 0.9300 . ? C34 C35 1.363(9) . ? C34 H34 0.9300 . ? C35 C36 1.379(8) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C37 C42 1.378(6) . ? C37 C38 1.392(6) . ? C38 C39 1.379(6) . ? C38 H38 0.9300 . ? C39 C40 1.379(7) . ? C39 H39 0.9300 . ? C40 C41 1.372(7) . ? C40 C43 1.525(6) . ? C41 C42 1.378(6) . ? C41 H41 0.9300 . ? C42 H42 0.9300 . ? C43 H43A 0.9600 . ? C43 H43B 0.9600 . ? C43 H43C 0.9600 . ? C44 H44A 0.9600 . ? C44 H44B 0.9600 . ? C44 H44C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Re1 O1 172.20(12) . . ? N2 Re1 Cl2 101.94(9) . . ? O1 Re1 Cl2 85.82(8) . . ? N2 Re1 Cl1 89.18(9) . . ? O1 Re1 Cl1 83.07(8) . . ? Cl2 Re1 Cl1 168.87(4) . . ? N2 Re1 P1 90.58(10) . . ? O1 Re1 P1 89.23(8) . . ? Cl2 Re1 P1 85.59(3) . . ? Cl1 Re1 P1 94.93(4) . . ? N2 Re1 P2 89.44(10) . . ? O1 Re1 P2 91.19(8) . . ? Cl2 Re1 P2 91.27(3) . . ? Cl1 Re1 P2 88.27(4) . . ? P1 Re1 P2 176.80(3) . . ? C37 N2 Re1 161.5(3) . . ? C44 O1 Re1 142.9(3) . . ? C7 P1 C1 104.44(16) . . ? C7 P1 C13 105.67(17) . . ? C1 P1 C13 101.22(17) . . ? C7 P1 Re1 112.34(13) . . ? C1 P1 Re1 114.25(13) . . ? C13 P1 Re1 117.50(12) . . ? C31 P2 C19 102.91(18) . . ? C31 P2 C25 108.3(2) . . ? C19 P2 C25 101.13(19) . . ? C31 P2 Re1 113.84(15) . . ? C19 P2 Re1 117.05(13) . . ? C25 P2 Re1 112.42(15) . . ? C6 C1 C2 118.5(3) . . ? C6 C1 P1 119.8(3) . . ? C2 C1 P1 121.5(3) . . ? C3 C2 C1 119.8(4) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C4 C3 C2 121.0(4) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 119.6(4) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C4 C5 C6 120.3(4) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C1 C6 C5 120.7(4) . . ? C1 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C8 C7 C12 119.1(4) . . ? C8 C7 P1 122.4(3) . . ? C12 C7 P1 118.5(3) . . ? C7 C8 C9 120.5(4) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C10 C9 C8 120.3(4) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 119.6(4) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C12 C11 C10 120.4(4) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C7 120.1(4) . . ? C11 C12 H12 120.0 . . ? C7 C12 H12 120.0 . . ? C18 C13 C14 118.1(4) . . ? C18 C13 P1 122.7(3) . . ? C14 C13 P1 119.2(3) . . ? C15 C14 C13 120.0(4) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C16 C15 C14 121.2(4) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C17 119.3(4) . . ? C15 C16 H16 120.3 . . ? C17 C16 H16 120.3 . . ? C16 C17 C18 119.8(4) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C13 C18 C17 121.6(4) . . ? C13 C18 H18 119.2 . . ? C17 C18 H18 119.2 . . ? C20 C19 C24 118.8(4) . . ? C20 C19 P2 120.2(3) . . ? C24 C19 P2 120.7(3) . . ? C19 C20 C21 121.2(4) . . ? C19 C20 H20 119.4 . . ? C21 C20 H20 119.4 . . ? C22 C21 C20 119.8(4) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C23 C22 C21 119.6(4) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? C22 C23 C24 121.1(4) . . ? C22 C23 H23 119.5 . . ? C24 C23 H23 119.5 . . ? C23 C24 C19 119.4(4) . . ? C23 C24 H24 120.3 . . ? C19 C24 H24 120.3 . . ? C26 C25 C30 118.1(4) . . ? C26 C25 P2 121.2(3) . . ? C30 C25 P2 120.3(4) . . ? C25 C26 C27 120.7(5) . . ? C25 C26 H26 119.6 . . ? C27 C26 H26 119.6 . . ? C28 C27 C26 119.6(6) . . ? C28 C27 H27 120.2 . . ? C26 C27 H27 120.2 . . ? C29 C28 C27 120.5(5) . . ? C29 C28 H28 119.8 . . ? C27 C28 H28 119.8 . . ? C28 C29 C30 120.9(6) . . ? C28 C29 H29 119.5 . . ? C30 C29 H29 119.5 . . ? C25 C30 C29 120.2(5) . . ? C25 C30 H30 119.9 . . ? C29 C30 H30 119.9 . . ? C32 C31 C36 119.6(4) . . ? C32 C31 P2 116.3(3) . . ? C36 C31 P2 124.1(4) . . ? C31 C32 C33 120.1(5) . . ? C31 C32 H32 120.0 . . ? C33 C32 H32 120.0 . . ? C34 C33 C32 119.8(6) . . ? C34 C33 H33 120.1 . . ? C32 C33 H33 120.1 . . ? C35 C34 C33 120.7(6) . . ? C35 C34 H34 119.7 . . ? C33 C34 H34 119.7 . . ? C34 C35 C36 120.1(6) . . ? C34 C35 H35 120.0 . . ? C36 C35 H35 120.0 . . ? C35 C36 C31 119.8(6) . . ? C35 C36 H36 120.1 . . ? C31 C36 H36 120.1 . . ? C42 C37 N2 120.6(4) . . ? C42 C37 C38 119.9(4) . . ? N2 C37 C38 119.5(4) . . ? C39 C38 C37 119.1(5) . . ? C39 C38 H38 120.5 . . ? C37 C38 H38 120.5 . . ? C40 C39 C38 121.3(5) . . ? C40 C39 H39 119.3 . . ? C38 C39 H39 119.3 . . ? C41 C40 C39 118.7(4) . . ? C41 C40 C43 120.8(5) . . ? C39 C40 C43 120.5(5) . . ? C40 C41 C42 121.4(5) . . ? C40 C41 H41 119.3 . . ? C42 C41 H41 119.3 . . ? C41 C42 C37 119.6(4) . . ? C41 C42 H42 120.2 . . ? C37 C42 H42 120.2 . . ? C40 C43 H43A 109.5 . . ? C40 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C40 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? O1 C44 H44A 109.5 . . ? O1 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? O1 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C14 H14 Cl1 0.93 2.62 3.298(5) 130.3 . C24 H24 Cl2 0.93 2.76 3.264(4) 114.9 . C30 H30 Cl1 0.93 2.67 3.196(5) 116.7 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.951 _refine_diff_density_min -0.711 _refine_diff_density_rms 0.085 _database_code_depnum_ccdc_archive 'CCDC 936244' ####################################################################### # # 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_ren375 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H41 Br2 N O1 P2 Re, 0.5 O' _chemical_formula_sum 'C44 H41 Br2 N O1.50 P2 Re' _chemical_formula_weight 1015.74 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' Br Br -0.2901 2.4595 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.5826(5) _cell_length_b 13.5937(6) _cell_length_c 14.4529(5) _cell_angle_alpha 87.048(3) _cell_angle_beta 88.440(4) _cell_angle_gamma 81.771(4) _cell_volume 2054.59(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8236 _cell_measurement_theta_min 3.8470 _cell_measurement_theta_max 28.2980 _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.11779 _exptl_crystal_size_mid 0.08747 _exptl_crystal_size_min 0.06172 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.642 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 998 _exptl_absorpt_coefficient_mu 5.015 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details ;CrysAlis RED, (2005) ; _exptl_absorpt_correction_T_min 0.50725 _exptl_absorpt_correction_T_max 1.00000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20093 _diffrn_reflns_av_R_equivalents 0.0588 _diffrn_reflns_av_unetI/netI 0.0660 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7210 _reflns_number_gt 5896 _reflns_threshold_expression >2sigma(I) #========================================================================== # # REFINEMENT DATA _computing_data_collection 'CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000)' _computing_cell_refinement 'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)' _computing_data_reduction 'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;XP in SHELXTL/PC (Sheldrick, 1990b) ORTEP-3 W v. 1.062 (Farrugia 1997) ; _computing_publication_material ;SHELXL-97 (Sheldrick, 1997) and PLATON (Spek, 1990) ; _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^)+(0.0410P)^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 7210 _refine_ls_number_parameters 480 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0901 _refine_ls_wR_factor_gt 0.0826 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _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 0.684378(19) 0.805256(15) 0.220910(15) 0.03161(9) Uani 1 1 d . . . Br1 Br 0.60586(7) 0.74841(5) 0.38481(5) 0.05914(19) Uani 1 1 d . . . Br2 Br 0.73467(6) 0.88561(4) 0.06349(4) 0.04749(16) Uani 1 1 d . . . P1 P 0.61281(13) 0.67204(10) 0.12990(10) 0.0342(3) Uani 1 1 d . . . P2 P 0.73775(12) 0.95674(10) 0.29521(10) 0.0308(3) Uani 1 1 d . . . O1 O 0.5151(3) 0.8731(3) 0.2104(3) 0.0398(9) Uani 1 1 d . . . N2 N 0.8301(4) 0.7310(3) 0.2432(3) 0.0384(11) Uani 1 1 d . . . C1 C 0.5932(5) 1.0467(4) 0.2963(4) 0.0346(13) Uani 1 1 d . . . C2 C 0.5204(5) 1.0698(4) 0.3758(4) 0.0416(14) Uani 1 1 d . . . H2 H 0.5492 1.0429 0.4332 0.050 Uiso 1 1 calc R . . C3 C 0.4061(5) 1.1320(5) 0.3702(5) 0.0530(17) Uani 1 1 d . . . H3 H 0.3591 1.1476 0.4241 0.064 Uiso 1 1 calc R . . C4 C 0.3609(6) 1.1711(5) 0.2872(5) 0.0533(17) Uani 1 1 d . . . H4 H 0.2836 1.2132 0.2840 0.064 Uiso 1 1 calc R . . C5 C 0.4313(5) 1.1473(5) 0.2080(5) 0.0496(16) Uani 1 1 d . . . H5 H 0.4005 1.1732 0.1508 0.060 Uiso 1 1 calc R . . C6 C 0.5458(5) 1.0864(4) 0.2120(4) 0.0390(13) Uani 1 1 d . . . H6 H 0.5921 1.0715 0.1576 0.047 Uiso 1 1 calc R . . C7 C 0.8000(5) 0.9450(4) 0.4125(4) 0.0354(13) Uani 1 1 d . . . C8 C 0.7940(5) 1.0280(5) 0.4662(4) 0.0464(15) Uani 1 1 d . . . H8 H 0.7560 1.0900 0.4430 0.056 Uiso 1 1 calc R . . C9 C 0.8449(6) 1.0181(6) 0.5547(5) 0.0583(19) Uani 1 1 d . . . H9 H 0.8389 1.0731 0.5910 0.070 Uiso 1 1 calc R . . C10 C 0.9035(6) 0.9282(6) 0.5879(4) 0.0566(18) Uani 1 1 d . . . H10 H 0.9370 0.9220 0.6471 0.068 Uiso 1 1 calc R . . C11 C 0.9136(6) 0.8476(6) 0.5356(5) 0.0581(18) Uani 1 1 d . . . H11 H 0.9556 0.7867 0.5585 0.070 Uiso 1 1 calc R . . C12 C 0.8614(5) 0.8554(5) 0.4478(4) 0.0453(15) Uani 1 1 d . . . H12 H 0.8680 0.7995 0.4125 0.054 Uiso 1 1 calc R . . C13 C 0.8560(5) 1.0233(4) 0.2347(4) 0.0324(12) Uani 1 1 d . . . C14 C 0.8487(5) 1.1260(4) 0.2360(4) 0.0400(14) Uani 1 1 d . . . H14 H 0.7789 1.1627 0.2646 0.048 Uiso 1 1 calc R . . C15 C 0.9438(6) 1.1746(5) 0.1952(5) 0.0503(16) Uani 1 1 d . . . H15 H 0.9380 1.2434 0.1976 0.060 Uiso 1 1 calc R . . C16 C 1.0466(6) 1.1221(5) 0.1515(4) 0.0534(17) Uani 1 1 d . . . H16 H 1.1101 1.1551 0.1239 0.064 Uiso 1 1 calc R . . C17 C 1.0551(6) 1.0204(5) 0.1486(5) 0.0566(17) Uani 1 1 d . . . H17 H 1.1242 0.9845 0.1184 0.068 Uiso 1 1 calc R . . C18 C 0.9606(5) 0.9713(4) 0.1906(4) 0.0462(15) Uani 1 1 d . . . H18 H 0.9677 0.9024 0.1891 0.055 Uiso 1 1 calc R . . C19 C 0.4503(5) 0.7067(4) 0.0879(4) 0.0347(13) Uani 1 1 d . . . C20 C 0.4164(5) 0.7989(4) 0.0404(4) 0.0432(14) Uani 1 1 d . . . H20 H 0.4776 0.8407 0.0278 0.052 Uiso 1 1 calc R . . C21 C 0.2921(5) 0.8277(4) 0.0122(4) 0.0459(15) Uani 1 1 d . . . H21 H 0.2702 0.8890 -0.0193 0.055 Uiso 1 1 calc R . . C22 C 0.2010(6) 0.7667(5) 0.0304(4) 0.0514(16) Uani 1 1 d . . . H22 H 0.1172 0.7873 0.0126 0.062 Uiso 1 1 calc R . . C23 C 0.2332(6) 0.6757(5) 0.0747(5) 0.0557(18) Uani 1 1 d . . . H23 H 0.1714 0.6341 0.0859 0.067 Uiso 1 1 calc R . . C24 C 0.3577(5) 0.6447(4) 0.1033(4) 0.0480(16) Uani 1 1 d . . . H24 H 0.3789 0.5823 0.1327 0.058 Uiso 1 1 calc R . . C25 C 0.6096(5) 0.5488(4) 0.1854(4) 0.0368(14) Uani 1 1 d . . . C26 C 0.6608(6) 0.4621(4) 0.1412(5) 0.0489(16) Uani 1 1 d . . . H26 H 0.7006 0.4666 0.0833 0.059 Uiso 1 1 calc R . . C27 C 0.6517(7) 0.3702(5) 0.1841(6) 0.065(2) Uani 1 1 d . . . H27 H 0.6858 0.3127 0.1548 0.078 Uiso 1 1 calc R . . C28 C 0.5936(6) 0.3628(5) 0.2688(6) 0.0618(19) Uani 1 1 d . . . H28 H 0.5875 0.3005 0.2969 0.074 Uiso 1 1 calc R . . C29 C 0.5436(6) 0.4477(5) 0.3131(5) 0.0606(18) Uani 1 1 d . . . H29 H 0.5052 0.4425 0.3715 0.073 Uiso 1 1 calc R . . C30 C 0.5505(6) 0.5393(5) 0.2715(5) 0.0494(16) Uani 1 1 d . . . H30 H 0.5150 0.5960 0.3014 0.059 Uiso 1 1 calc R . . C31 C 0.7113(5) 0.6447(4) 0.0260(4) 0.0352(13) Uani 1 1 d . . . C32 C 0.8429(5) 0.6375(4) 0.0296(4) 0.0478(16) Uani 1 1 d . . . H32 H 0.8805 0.6499 0.0845 0.057 Uiso 1 1 calc R . . C33 C 0.9187(6) 0.6124(5) -0.0467(5) 0.0527(17) Uani 1 1 d . . . H33 H 1.0071 0.6064 -0.0424 0.063 Uiso 1 1 calc R . . C34 C 0.8662(6) 0.5961(5) -0.1284(5) 0.0544(17) Uani 1 1 d . . . H34 H 0.9180 0.5803 -0.1801 0.065 Uiso 1 1 calc R . . C35 C 0.7345(7) 0.6033(5) -0.1336(4) 0.0549(17) Uani 1 1 d . . . H35 H 0.6975 0.5916 -0.1889 0.066 Uiso 1 1 calc R . . C36 C 0.6599(6) 0.6274(4) -0.0584(4) 0.0464(15) Uani 1 1 d . . . H36 H 0.5717 0.6325 -0.0631 0.056 Uiso 1 1 calc R . . C37 C 0.9211(5) 0.6570(5) 0.2825(4) 0.0482(16) Uani 1 1 d . . . C38 C 0.8878(7) 0.5696(5) 0.3253(5) 0.065(2) Uani 1 1 d . . . H38 H 0.8027 0.5593 0.3264 0.077 Uiso 1 1 calc R . . C39 C 0.9755(7) 0.4999(6) 0.3649(5) 0.069(2) Uani 1 1 d . . . H39 H 0.9491 0.4434 0.3938 0.083 Uiso 1 1 calc R . . C40 C 1.1025(7) 0.5097(6) 0.3640(5) 0.071(2) Uani 1 1 d . . . C41 C 1.1381(6) 0.5943(7) 0.3211(6) 0.082(3) Uani 1 1 d . . . H41 H 1.2238 0.6030 0.3199 0.099 Uiso 1 1 calc R . . C42 C 1.0488(6) 0.6678(6) 0.2793(5) 0.074(2) Uani 1 1 d . . . H42 H 1.0754 0.7238 0.2495 0.089 Uiso 1 1 calc R . . C43 C 1.2002(8) 0.4305(7) 0.4095(6) 0.099(3) Uani 1 1 d . . . H43A H 1.1571 0.3868 0.4494 0.148 Uiso 1 1 calc R . . H43B H 1.2571 0.4617 0.4452 0.148 Uiso 1 1 calc R . . H43C H 1.2481 0.3929 0.3625 0.148 Uiso 1 1 calc R . . C44 C 0.3926(5) 0.8855(5) 0.2515(5) 0.0552(17) Uani 1 1 d . . . H44A H 0.3521 0.8280 0.2420 0.083 Uiso 1 1 calc R . . H44B H 0.3425 0.9435 0.2239 0.083 Uiso 1 1 calc R . . H44C H 0.3992 0.8933 0.3168 0.083 Uiso 1 1 calc R . . O99 O 0.337(4) 0.653(2) 0.4720(18) 0.144(16) Uani 0.25 1 d P A 1 O99' O 0.296(3) 0.710(2) 0.499(2) 0.140(15) Uani 0.25 1 d P B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Re1 0.03467(13) 0.03068(14) 0.03007(14) -0.00390(9) 0.00014(9) -0.00588(9) Br1 0.0715(4) 0.0688(5) 0.0419(4) -0.0018(3) 0.0038(3) -0.0275(4) Br2 0.0645(4) 0.0430(4) 0.0369(4) -0.0025(3) 0.0039(3) -0.0152(3) P1 0.0377(7) 0.0285(8) 0.0373(9) -0.0052(6) -0.0028(6) -0.0060(6) P2 0.0322(7) 0.0329(8) 0.0279(8) -0.0042(6) 0.0014(6) -0.0066(6) O1 0.038(2) 0.038(2) 0.046(3) -0.0138(18) -0.0040(18) -0.0058(17) N2 0.034(2) 0.045(3) 0.036(3) -0.003(2) 0.008(2) -0.006(2) C1 0.032(3) 0.033(3) 0.040(4) -0.009(2) 0.002(2) -0.008(2) C2 0.040(3) 0.054(4) 0.032(3) -0.004(3) 0.005(3) -0.011(3) C3 0.045(3) 0.061(4) 0.053(5) -0.016(3) 0.014(3) -0.005(3) C4 0.041(3) 0.049(4) 0.068(5) -0.008(3) 0.004(3) 0.002(3) C5 0.050(4) 0.050(4) 0.046(4) 0.005(3) -0.002(3) 0.001(3) C6 0.039(3) 0.041(3) 0.035(3) 0.001(3) 0.004(3) -0.001(3) C7 0.033(3) 0.046(4) 0.028(3) -0.003(3) -0.001(2) -0.011(3) C8 0.044(3) 0.059(4) 0.040(4) -0.009(3) -0.001(3) -0.017(3) C9 0.053(4) 0.087(5) 0.045(4) -0.025(4) 0.003(3) -0.037(4) C10 0.046(4) 0.096(6) 0.032(4) 0.006(4) -0.007(3) -0.027(4) C11 0.044(4) 0.078(5) 0.052(5) 0.014(4) -0.011(3) -0.013(3) C12 0.040(3) 0.049(4) 0.047(4) -0.002(3) -0.004(3) -0.007(3) C13 0.030(3) 0.040(3) 0.027(3) 0.000(2) 0.000(2) -0.006(2) C14 0.037(3) 0.034(3) 0.047(4) 0.001(3) 0.004(3) -0.002(2) C15 0.052(4) 0.044(4) 0.057(4) 0.008(3) -0.008(3) -0.014(3) C16 0.044(4) 0.075(5) 0.045(4) 0.007(3) 0.001(3) -0.025(3) C17 0.042(3) 0.077(5) 0.051(4) -0.010(4) 0.016(3) -0.009(3) C18 0.045(3) 0.042(4) 0.052(4) -0.014(3) 0.003(3) -0.007(3) C19 0.038(3) 0.032(3) 0.033(3) -0.010(2) -0.002(2) 0.001(2) C20 0.043(3) 0.036(3) 0.050(4) -0.006(3) 0.000(3) -0.003(3) C21 0.054(4) 0.043(4) 0.038(4) 0.002(3) -0.005(3) 0.004(3) C22 0.047(3) 0.066(5) 0.039(4) -0.003(3) -0.009(3) 0.002(3) C23 0.043(3) 0.064(5) 0.063(5) -0.006(4) -0.008(3) -0.016(3) C24 0.054(4) 0.038(4) 0.054(4) -0.006(3) -0.013(3) -0.011(3) C25 0.038(3) 0.029(3) 0.044(4) -0.006(3) -0.012(3) -0.004(2) C26 0.054(4) 0.038(4) 0.054(4) -0.005(3) -0.007(3) -0.001(3) C27 0.083(5) 0.031(4) 0.079(6) 0.000(4) -0.010(4) -0.002(3) C28 0.071(4) 0.037(4) 0.076(6) 0.010(4) -0.006(4) -0.007(3) C29 0.070(4) 0.058(5) 0.056(5) 0.010(4) 0.005(4) -0.021(4) C30 0.055(4) 0.044(4) 0.050(4) -0.004(3) 0.004(3) -0.011(3) C31 0.048(3) 0.026(3) 0.033(3) -0.006(2) 0.000(3) -0.008(2) C32 0.048(3) 0.048(4) 0.046(4) -0.012(3) -0.002(3) 0.000(3) C33 0.043(3) 0.058(4) 0.058(5) -0.013(3) 0.009(3) -0.008(3) C34 0.069(4) 0.049(4) 0.046(4) -0.010(3) 0.021(3) -0.013(3) C35 0.080(5) 0.048(4) 0.036(4) -0.006(3) 0.002(3) -0.005(3) C36 0.048(3) 0.042(4) 0.051(4) -0.006(3) -0.007(3) -0.007(3) C37 0.044(3) 0.061(4) 0.037(4) -0.006(3) -0.004(3) 0.003(3) C38 0.064(4) 0.055(4) 0.069(5) 0.014(4) -0.007(4) 0.005(4) C39 0.071(5) 0.068(5) 0.063(5) 0.009(4) -0.002(4) 0.005(4) C40 0.071(5) 0.082(6) 0.048(5) 0.002(4) -0.002(4) 0.023(4) C41 0.043(4) 0.102(7) 0.092(7) 0.023(5) 0.001(4) 0.010(4) C42 0.047(4) 0.087(6) 0.081(6) 0.025(5) 0.008(4) -0.001(4) C43 0.087(6) 0.100(7) 0.092(7) 0.024(5) 0.006(5) 0.036(5) C44 0.035(3) 0.066(5) 0.065(5) -0.021(4) 0.007(3) -0.006(3) O99 0.25(4) 0.16(3) 0.065(18) 0.040(18) -0.06(2) -0.19(3) O99' 0.18(3) 0.08(2) 0.12(3) 0.027(17) 0.06(2) 0.10(2) _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 N2 1.746(4) . ? Re1 O1 1.900(3) . ? Re1 P1 2.5050(13) . ? Re1 P2 2.5112(13) . ? Re1 Br2 2.5490(7) . ? Re1 Br1 2.6052(7) . ? P1 C25 1.825(6) . ? P1 C31 1.829(6) . ? P1 C19 1.829(5) . ? P2 C1 1.817(5) . ? P2 C13 1.826(5) . ? P2 C7 1.826(5) . ? O1 C44 1.403(7) . ? N2 C37 1.399(7) . ? C1 C6 1.384(7) . ? C1 C2 1.390(8) . ? C2 C3 1.375(8) . ? C2 H2 0.9300 . ? C3 C4 1.357(9) . ? C3 H3 0.9300 . ? C4 C5 1.376(9) . ? C4 H4 0.9300 . ? C5 C6 1.367(7) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.376(8) . ? C7 C8 1.396(8) . ? C8 C9 1.394(8) . ? C8 H8 0.9300 . ? C9 C10 1.360(9) . ? C9 H9 0.9300 . ? C10 C11 1.353(10) . ? C10 H10 0.9300 . ? C11 C12 1.391(8) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C18 1.384(8) . ? C13 C14 1.388(7) . ? C14 C15 1.383(8) . ? C14 H14 0.9300 . ? C15 C16 1.371(9) . ? C15 H15 0.9300 . ? C16 C17 1.375(9) . ? C16 H16 0.9300 . ? C17 C18 1.390(8) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C24 1.388(8) . ? C19 C20 1.402(8) . ? C20 C21 1.384(7) . ? C20 H20 0.9300 . ? C21 C22 1.371(8) . ? C21 H21 0.9300 . ? C22 C23 1.367(9) . ? C22 H22 0.9300 . ? C23 C24 1.391(8) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C30 1.386(8) . ? C25 C26 1.402(8) . ? C26 C27 1.381(9) . ? C26 H26 0.9300 . ? C27 C28 1.361(10) . ? C27 H27 0.9300 . ? C28 C29 1.380(10) . ? C28 H28 0.9300 . ? C29 C30 1.364(8) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 C32 1.384(7) . ? C31 C36 1.393(7) . ? C32 C33 1.375(9) . ? C32 H32 0.9300 . ? C33 C34 1.360(8) . ? C33 H33 0.9300 . ? C34 C35 1.387(8) . ? C34 H34 0.9300 . ? C35 C36 1.352(9) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C37 C42 1.379(8) . ? C37 C38 1.397(9) . ? C38 C39 1.344(9) . ? C38 H38 0.9300 . ? C39 C40 1.370(10) . ? C39 H39 0.9300 . ? C40 C41 1.374(11) . ? C40 C43 1.518(9) . ? C41 C42 1.398(10) . ? C41 H41 0.9300 . ? C42 H42 0.9300 . ? C43 H43A 0.9600 . ? C43 H43B 0.9600 . ? C43 H43C 0.9600 . ? C44 H44A 0.9600 . ? C44 H44B 0.9600 . ? C44 H44C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Re1 O1 171.23(19) . . ? N2 Re1 P1 91.02(15) . . ? O1 Re1 P1 86.73(10) . . ? N2 Re1 P2 96.03(15) . . ? O1 Re1 P2 87.00(10) . . ? P1 Re1 P2 171.45(4) . . ? N2 Re1 Br2 100.44(16) . . ? O1 Re1 Br2 87.84(12) . . ? P1 Re1 Br2 85.32(4) . . ? P2 Re1 Br2 88.64(4) . . ? N2 Re1 Br1 87.88(16) . . ? O1 Re1 Br1 84.09(12) . . ? P1 Re1 Br1 98.60(4) . . ? P2 Re1 Br1 86.52(4) . . ? Br2 Re1 Br1 170.79(2) . . ? C25 P1 C31 102.6(3) . . ? C25 P1 C19 103.4(2) . . ? C31 P1 C19 105.0(2) . . ? C25 P1 Re1 119.02(18) . . ? C31 P1 Re1 112.98(16) . . ? C19 P1 Re1 112.35(17) . . ? C1 P2 C13 104.3(2) . . ? C1 P2 C7 107.4(3) . . ? C13 P2 C7 100.7(2) . . ? C1 P2 Re1 107.14(16) . . ? C13 P2 Re1 116.62(18) . . ? C7 P2 Re1 119.55(19) . . ? C44 O1 Re1 144.7(4) . . ? C37 N2 Re1 161.0(4) . . ? C6 C1 C2 118.0(5) . . ? C6 C1 P2 117.9(4) . . ? C2 C1 P2 123.7(4) . . ? C3 C2 C1 120.5(5) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C4 C3 C2 121.0(6) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 118.9(6) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C6 C5 C4 121.1(6) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C1 120.4(5) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? C12 C7 C8 118.3(5) . . ? C12 C7 P2 120.8(4) . . ? C8 C7 P2 120.8(4) . . ? C9 C8 C7 120.0(6) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C10 C9 C8 120.2(6) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C11 C10 C9 120.6(6) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 120.2(6) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C7 C12 C11 120.7(6) . . ? C7 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C18 C13 C14 117.9(5) . . ? C18 C13 P2 120.3(4) . . ? C14 C13 P2 121.7(4) . . ? C15 C14 C13 121.0(5) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C16 C15 C14 120.4(6) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C17 119.6(6) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C16 C17 C18 120.0(6) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C13 C18 C17 121.0(6) . . ? C13 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C24 C19 C20 118.5(5) . . ? C24 C19 P1 121.7(4) . . ? C20 C19 P1 119.8(4) . . ? C21 C20 C19 120.2(5) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C22 C21 C20 120.5(6) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C23 C22 C21 120.0(5) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C22 C23 C24 120.6(6) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C19 C24 C23 120.1(6) . . ? C19 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C30 C25 C26 118.6(5) . . ? C30 C25 P1 119.9(4) . . ? C26 C25 P1 121.5(5) . . ? C27 C26 C25 119.6(7) . . ? C27 C26 H26 120.2 . . ? C25 C26 H26 120.2 . . ? C28 C27 C26 120.7(7) . . ? C28 C27 H27 119.6 . . ? C26 C27 H27 119.6 . . ? C27 C28 C29 120.1(6) . . ? C27 C28 H28 120.0 . . ? C29 C28 H28 120.0 . . ? C30 C29 C28 120.1(7) . . ? C30 C29 H29 119.9 . . ? C28 C29 H29 119.9 . . ? C29 C30 C25 120.9(6) . . ? C29 C30 H30 119.5 . . ? C25 C30 H30 119.5 . . ? C32 C31 C36 117.2(5) . . ? C32 C31 P1 120.1(4) . . ? C36 C31 P1 122.6(4) . . ? C33 C32 C31 120.9(5) . . ? C33 C32 H32 119.6 . . ? C31 C32 H32 119.6 . . ? C34 C33 C32 120.8(6) . . ? C34 C33 H33 119.6 . . ? C32 C33 H33 119.6 . . ? C33 C34 C35 119.2(6) . . ? C33 C34 H34 120.4 . . ? C35 C34 H34 120.4 . . ? C36 C35 C34 120.0(6) . . ? C36 C35 H35 120.0 . . ? C34 C35 H35 120.0 . . ? C35 C36 C31 121.9(5) . . ? C35 C36 H36 119.1 . . ? C31 C36 H36 119.1 . . ? C42 C37 C38 117.4(6) . . ? C42 C37 N2 120.5(6) . . ? C38 C37 N2 122.1(5) . . ? C39 C38 C37 121.7(7) . . ? C39 C38 H38 119.2 . . ? C37 C38 H38 119.2 . . ? C38 C39 C40 122.0(8) . . ? C38 C39 H39 119.0 . . ? C40 C39 H39 119.0 . . ? C39 C40 C41 117.5(6) . . ? C39 C40 C43 121.3(8) . . ? C41 C40 C43 121.3(7) . . ? C40 C41 C42 121.7(7) . . ? C40 C41 H41 119.2 . . ? C42 C41 H41 119.2 . . ? C37 C42 C41 119.8(7) . . ? C37 C42 H42 120.1 . . ? C41 C42 H42 120.1 . . ? C40 C43 H43A 109.5 . . ? C40 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C40 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? O1 C44 H44A 109.5 . . ? O1 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? O1 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C30 H30 Br1 0.93 2.75 3.481(6) 136.2 . C32 H32 N2 0.93 2.61 3.390(8) 142.4 . C44 H44C Br1 0.96 2.88 3.308(6) 107.9 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.867 _refine_diff_density_min -1.218 _refine_diff_density_rms 0.130 _database_code_depnum_ccdc_archive 'CCDC 936245'