# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_bb092b #TrackingRef 'web_deposit_cif_file_0_BrianSkelton_1366179046.bb092b.cif' _audit_creation_date 2011-08-01T15:14:49-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C17 H11 Cl N3 O3 Re' _chemical_formula_moiety 'C17 H11 Cl N3 O3 Re' _chemical_formula_weight 526.94 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-p 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.55800(10) _cell_length_b 8.39400(10) _cell_length_c 16.9605(2) _cell_angle_alpha 90 _cell_angle_beta 96.2870(10) _cell_angle_gamma 90 _cell_volume 1635.57(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 44102 _cell_measurement_theta_min 3.853 _cell_measurement_theta_max 45.5697 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.056 _exptl_crystal_density_diffrn 2.14 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 0 0 0.094 1 0 0 0.0526 8 1 0 0.0739 7 -3 0 0.0511 0 1 -1 0.1975 0 1 1 0.2258 0 0 1 0.0385 0 0 -1 0.0185 -3 -1 0 0.1542 -16 3 1 0.1237 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 7.615 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_absorpt_correction_T_min 0.128 _exptl_absorpt_correction_T_max 0.656 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4738 _diffrn_orient_matrix_ub_11 -0.0586347789 _diffrn_orient_matrix_ub_12 -0.0181845954 _diffrn_orient_matrix_ub_13 0.0049184199 _diffrn_orient_matrix_ub_21 -0.0141795304 _diffrn_orient_matrix_ub_22 0.0007152568 _diffrn_orient_matrix_ub_23 -0.0417260654 _diffrn_orient_matrix_ub_31 0.0127245327 _diffrn_orient_matrix_ub_32 -0.0824053506 _diffrn_orient_matrix_ub_33 -0.0014214816 _diffrn_measurement_device_type 'Oxford Diffraction Gemini diffractometer' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_unetI/netI 0.033 _diffrn_reflns_number 96088 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 3.86 _diffrn_reflns_theta_max 45.71 _diffrn_reflns_theta_full 45.71 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 13943 _reflns_number_gt 10775 _reflns_threshold_expression I>2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'OrtepII (Johnson, C. K. (1976)' _computing_publication_material 'WinGX Farrugia, L. J. (1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0145P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 13943 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0285 _refine_ls_R_factor_gt 0.0174 _refine_ls_wR_factor_ref 0.0329 _refine_ls_wR_factor_gt 0.0321 _refine_ls_goodness_of_fit_ref 0.883 _refine_ls_restrained_S_all 0.883 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.657 _refine_diff_density_min -0.834 _refine_diff_density_rms 0.136 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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 7.231 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.693773(3) 0.214598(4) 0.475719(2) 0.009270(10) Uani 1 1 d . . . C1 C 0.60847(9) 0.10178(12) 0.38670(7) 0.01440(17) Uani 1 1 d . . . O1 O 0.56257(8) 0.03038(11) 0.33492(6) 0.02461(18) Uani 1 1 d . . . C2 C 0.68007(9) 0.02605(12) 0.53779(7) 0.01527(17) Uani 1 1 d . . . O2 O 0.67111(9) -0.08808(11) 0.57395(6) 0.02565(19) Uani 1 1 d . . . C3 C 0.55195(9) 0.29032(13) 0.51074(6) 0.01474(16) Uani 1 1 d . . . O3 O 0.46574(7) 0.33240(11) 0.53201(6) 0.02264(17) Uani 1 1 d . . . Cl4 Cl 0.87793(2) 0.12195(3) 0.426305(16) 0.01384(4) Uani 1 1 d . . . N11 N 0.86718(7) 0.34566(10) 0.63058(5) 0.01199(13) Uani 1 1 d . . . C12 C 0.80696(8) 0.35344(11) 0.55800(6) 0.01086(14) Uani 1 1 d . . . N13 N 0.83718(8) 0.49884(10) 0.52959(5) 0.01203(13) Uani 1 1 d . . . C14 C 0.91551(10) 0.57932(12) 0.58382(7) 0.01574(17) Uani 1 1 d . . . H14 H 0.9492 0.681 0.5772 0.019 Uiso 1 1 calc R . . C15 C 0.93366(10) 0.48357(12) 0.64748(7) 0.01571(18) Uani 1 1 d . . . H15 H 0.9824 0.5053 0.6951 0.019 Uiso 1 1 calc R . . N21 N 0.72638(7) 0.43794(10) 0.41259(5) 0.01177(13) Uani 1 1 d . . . C22 C 0.79379(9) 0.54723(11) 0.45304(6) 0.01216(15) Uani 1 1 d . . . C23 C 0.81926(10) 0.69567(12) 0.42275(7) 0.01625(18) Uani 1 1 d . . . H23 H 0.8662 0.7704 0.4538 0.02 Uiso 1 1 calc R . . C24 C 0.77381(11) 0.73048(13) 0.34576(7) 0.01848(19) Uani 1 1 d . . . H24 H 0.789 0.8307 0.323 0.022 Uiso 1 1 calc R . . C25 C 0.70587(11) 0.61804(14) 0.30195(7) 0.0189(2) Uani 1 1 d . . . H25 H 0.6757 0.6391 0.2486 0.023 Uiso 1 1 calc R . . C26 C 0.68316(10) 0.47492(13) 0.33754(7) 0.01538(17) Uani 1 1 d . . . H26 H 0.6351 0.3993 0.308 0.018 Uiso 1 1 calc R . . C111 C 0.87272(8) 0.21227(12) 0.68401(6) 0.01179(14) Uani 1 1 d . . . C112 C 0.90502(9) 0.06416(12) 0.65764(6) 0.01435(17) Uani 1 1 d . . . H112 H 0.9207 0.0495 0.6043 0.017 Uiso 1 1 calc R . . C113 C 0.91401(10) -0.06247(13) 0.71073(7) 0.01675(18) Uani 1 1 d . . . H113 H 0.9352 -0.1649 0.6934 0.02 Uiso 1 1 calc R . . C114 C 0.89224(10) -0.04075(13) 0.78896(7) 0.01694(18) Uani 1 1 d . . . H114 H 0.8981 -0.1284 0.8246 0.02 Uiso 1 1 calc R . . C115 C 0.86197(10) 0.10891(13) 0.81513(7) 0.01578(17) Uani 1 1 d . . . H115 H 0.8482 0.124 0.8688 0.019 Uiso 1 1 calc R . . C116 C 0.85193(9) 0.23672(12) 0.76239(6) 0.01425(16) Uani 1 1 d . . . H116 H 0.8311 0.3394 0.7797 0.017 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 0.009590(10) 0.009890(10) 0.008290(10) -0.000410(10) 0.000810(10) -0.001010(10) C1 0.0142(4) 0.0155(4) 0.0132(4) -0.0009(3) 0.0000(3) 0.0011(3) O1 0.0256(4) 0.0264(4) 0.0197(4) -0.0079(3) -0.0074(3) 0.0006(3) C2 0.0158(4) 0.0161(4) 0.0135(4) -0.0006(3) -0.0005(3) -0.0046(3) O2 0.0331(5) 0.0221(4) 0.0204(4) 0.0073(3) -0.0030(4) -0.0117(3) C3 0.0140(4) 0.0168(4) 0.0134(4) -0.0020(4) 0.0010(3) -0.0024(3) O3 0.0156(3) 0.0284(4) 0.0247(5) -0.0068(3) 0.0058(3) 0.0008(3) Cl4 0.01230(9) 0.01268(9) 0.01711(11) -0.00163(7) 0.00426(8) -0.00010(7) N11 0.0128(3) 0.0119(3) 0.0110(3) -0.0010(3) 0.0003(3) -0.0012(3) C12 0.0114(3) 0.0108(3) 0.0103(4) -0.0010(3) 0.0014(3) -0.0005(3) N13 0.0140(3) 0.0111(3) 0.0110(3) -0.0009(3) 0.0011(3) -0.0020(3) C14 0.0173(4) 0.0135(4) 0.0161(5) -0.0023(3) 0.0004(3) -0.0050(3) C15 0.0167(4) 0.0152(4) 0.0146(5) -0.0022(3) -0.0012(3) -0.0047(3) N21 0.0139(3) 0.0111(3) 0.0105(3) 0.0006(3) 0.0023(3) 0.0012(3) C22 0.0131(4) 0.0121(4) 0.0117(4) 0.0001(3) 0.0032(3) 0.0007(3) C23 0.0204(4) 0.0126(4) 0.0163(5) 0.0012(3) 0.0046(4) -0.0011(3) C24 0.0236(5) 0.0151(4) 0.0176(5) 0.0051(4) 0.0060(4) 0.0010(4) C25 0.0239(5) 0.0200(5) 0.0128(5) 0.0047(4) 0.0021(4) 0.0028(4) C26 0.0178(4) 0.0160(4) 0.0121(4) 0.0009(3) 0.0008(3) 0.0018(3) C111 0.0119(3) 0.0127(3) 0.0105(4) -0.0006(3) 0.0000(3) -0.0001(3) C112 0.0153(4) 0.0161(4) 0.0117(4) -0.0025(3) 0.0016(3) 0.0012(3) C113 0.0200(5) 0.0139(4) 0.0162(5) -0.0007(3) 0.0010(4) 0.0022(3) C114 0.0192(5) 0.0167(4) 0.0144(5) 0.0017(3) -0.0006(4) -0.0009(3) C115 0.0167(4) 0.0198(4) 0.0109(4) -0.0003(3) 0.0019(3) -0.0006(3) C116 0.0154(4) 0.0155(4) 0.0118(4) -0.0021(3) 0.0014(3) 0.0010(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C3 1.9123(10) . ? Re1 C2 1.9169(11) . ? Re1 C1 1.9552(11) . ? Re1 C12 2.1488(10) . ? Re1 N21 2.2117(8) . ? Re1 Cl4 2.4956(2) . ? C1 O1 1.1444(14) . ? C2 O2 1.1484(14) . ? C3 O3 1.1518(13) . ? N11 C12 1.3477(13) . ? N11 C15 1.4016(13) . ? N11 C111 1.4373(13) . ? C12 N13 1.3714(13) . ? N13 C14 1.3927(14) . ? N13 C22 1.3999(14) . ? C14 C15 1.3439(16) . ? C14 H14 0.95 . ? C15 H15 0.95 . ? N21 C22 1.3425(13) . ? N21 C26 1.3515(14) . ? C22 C23 1.3914(14) . ? C23 C24 1.3843(17) . ? C23 H23 0.95 . ? C24 C25 1.3898(18) . ? C24 H24 0.95 . ? C25 C26 1.3825(15) . ? C25 H25 0.95 . ? C26 H26 0.95 . ? C111 C112 1.3862(14) . ? C111 C116 1.3918(14) . ? C112 C113 1.3895(16) . ? C112 H112 0.95 . ? C113 C114 1.3895(16) . ? C113 H113 0.95 . ? C114 C115 1.3897(16) . ? C114 H114 0.95 . ? C115 C116 1.3935(15) . ? C115 H115 0.95 . ? C116 H116 0.95 . ? 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 C3 Re1 C2 88.78(5) . . ? C3 Re1 C1 91.37(4) . . ? C2 Re1 C1 87.66(4) . . ? C3 Re1 C12 95.71(4) . . ? C2 Re1 C12 99.91(4) . . ? C1 Re1 C12 169.71(4) . . ? C3 Re1 N21 93.78(4) . . ? C2 Re1 N21 173.94(4) . . ? C1 Re1 N21 97.76(4) . . ? C12 Re1 N21 74.38(3) . . ? C3 Re1 Cl4 178.13(3) . . ? C2 Re1 Cl4 92.98(3) . . ? C1 Re1 Cl4 88.06(3) . . ? C12 Re1 Cl4 84.62(3) . . ? N21 Re1 Cl4 84.53(2) . . ? O1 C1 Re1 176.77(10) . . ? O2 C2 Re1 178.96(10) . . ? O3 C3 Re1 178.45(10) . . ? C12 N11 C15 111.32(9) . . ? C12 N11 C111 126.62(8) . . ? C15 N11 C111 121.93(9) . . ? N11 C12 N13 103.78(8) . . ? N11 C12 Re1 141.60(7) . . ? N13 C12 Re1 114.51(7) . . ? C12 N13 C14 111.82(9) . . ? C12 N13 C22 120.33(8) . . ? C14 N13 C22 127.79(9) . . ? C15 C14 N13 105.88(9) . . ? C15 C14 H14 127.1 . . ? N13 C14 H14 127.1 . . ? C14 C15 N11 107.20(9) . . ? C14 C15 H15 126.4 . . ? N11 C15 H15 126.4 . . ? C22 N21 C26 117.27(9) . . ? C22 N21 Re1 116.87(7) . . ? C26 N21 Re1 125.85(7) . . ? N21 C22 C23 123.90(10) . . ? N21 C22 N13 113.86(8) . . ? C23 C22 N13 122.24(9) . . ? C24 C23 C22 117.61(10) . . ? C24 C23 H23 121.2 . . ? C22 C23 H23 121.2 . . ? C23 C24 C25 119.66(10) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C26 C25 C24 118.67(11) . . ? C26 C25 H25 120.7 . . ? C24 C25 H25 120.7 . . ? N21 C26 C25 122.86(10) . . ? N21 C26 H26 118.6 . . ? C25 C26 H26 118.6 . . ? C112 C111 C116 121.41(9) . . ? C112 C111 N11 119.36(9) . . ? C116 C111 N11 119.13(9) . . ? C111 C112 C113 118.73(10) . . ? C111 C112 H112 120.6 . . ? C113 C112 H112 120.6 . . ? C114 C113 C112 120.66(10) . . ? C114 C113 H113 119.7 . . ? C112 C113 H113 119.7 . . ? C113 C114 C115 120.12(10) . . ? C113 C114 H114 119.9 . . ? C115 C114 H114 119.9 . . ? C114 C115 C116 119.81(10) . . ? C114 C115 H115 120.1 . . ? C116 C115 H115 120.1 . . ? C111 C116 C115 119.25(9) . . ? C111 C116 H116 120.4 . . ? C115 C116 H116 120.4 . . ? _database_code_depnum_ccdc_archive 'CCDC 934464' ####################################################################### # # 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_mxm51 #TrackingRef 'web_deposit_cif_file_1_BrianSkelton_1366179046.mxm51.cif' _audit_creation_date 2012-02-20T14:55:22-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C17 H11 Br N3 O3 Re' _chemical_formula_moiety 'C17 H11 Br N3 O3 Re' _chemical_formula_weight 571.4 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-p 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.7834(3) _cell_length_b 8.4832(3) _cell_length_c 17.0208(6) _cell_angle_alpha 90 _cell_angle_beta 96.719(3) _cell_angle_gamma 90 _cell_volume 1689.73(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 11903 _cell_measurement_theta_min 2.7972 _cell_measurement_theta_max 36.9583 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 2.246 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.0103 0 0 -1 0.0112 1 0 0 0.0385 -1 0 0 0.0423 0 1 0 0.099 0 -1 0 0.0903 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 9.578 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_absorpt_correction_T_min 0.268 _exptl_absorpt_correction_T_max 0.813 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 16.0009 _diffrn_orient_matrix_ub_11 0.052956 _diffrn_orient_matrix_ub_12 0.031141 _diffrn_orient_matrix_ub_13 -0.008725 _diffrn_orient_matrix_ub_21 -0.0165442 _diffrn_orient_matrix_ub_22 0.0759454 _diffrn_orient_matrix_ub_23 0.0119513 _diffrn_orient_matrix_ub_31 0.0243741 _diffrn_orient_matrix_ub_32 -0.0161468 _diffrn_orient_matrix_ub_33 0.0392504 _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur diffractometer' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0619 _diffrn_reflns_av_unetI/netI 0.05 _diffrn_reflns_number 26852 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 32 _diffrn_reflns_theta_full 32 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 5877 _reflns_number_gt 5175 _reflns_threshold_expression I>2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'OrtepII (Johnson, C. K. (1976)' _computing_publication_material 'WinGX Farrugia, L. J. (1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0188P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5877 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0323 _refine_ls_wR_factor_ref 0.0617 _refine_ls_wR_factor_gt 0.0591 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 2.138 _refine_diff_density_min -1.513 _refine_diff_density_rms 0.201 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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 7.231 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.688636(11) 0.214544(15) 0.476909(8) 0.00968(4) Uani 1 1 d . . . C1 C 0.6062(3) 0.1041(4) 0.3867(2) 0.0127(6) Uani 1 1 d . . . O1 O 0.5613(2) 0.0342(3) 0.33481(17) 0.0249(6) Uani 1 1 d . . . C2 C 0.6753(3) 0.0265(4) 0.5382(2) 0.0151(7) Uani 1 1 d . . . O2 O 0.6667(2) -0.0869(3) 0.57397(17) 0.0253(6) Uani 1 1 d . . . C3 C 0.5494(3) 0.2912(4) 0.5110(2) 0.0155(7) Uani 1 1 d . . . O3 O 0.4655(2) 0.3329(3) 0.53193(17) 0.0226(6) Uani 1 1 d . . . Br4 Br 0.87840(3) 0.11737(4) 0.42575(2) 0.01424(7) Uani 1 1 d . . . N11 N 0.8630(2) 0.3420(3) 0.63085(17) 0.0124(6) Uani 1 1 d . . . C12 C 0.8015(3) 0.3501(4) 0.5588(2) 0.0110(6) Uani 1 1 d . . . N13 N 0.8322(2) 0.4935(3) 0.53004(17) 0.0118(6) Uani 1 1 d . . . C14 C 0.9110(3) 0.5715(4) 0.5838(2) 0.0166(7) Uani 1 1 d . . . H14 H 0.9445 0.6716 0.5769 0.02 Uiso 1 1 calc R . . C15 C 0.9300(3) 0.4771(4) 0.6470(2) 0.0159(7) Uani 1 1 d . . . H15 H 0.9797 0.4978 0.6939 0.019 Uiso 1 1 calc R . . N21 N 0.7198(2) 0.4352(3) 0.41381(17) 0.0117(6) Uani 1 1 d . . . C22 C 0.7886(3) 0.5421(4) 0.4537(2) 0.0120(6) Uani 1 1 d . . . C23 C 0.8146(3) 0.6880(4) 0.4231(2) 0.0170(7) Uani 1 1 d . . . H23 H 0.8619 0.7617 0.4536 0.02 Uiso 1 1 calc R . . C24 C 0.7682(3) 0.7212(4) 0.3461(2) 0.0199(8) Uani 1 1 d . . . H24 H 0.7841 0.8193 0.3227 0.024 Uiso 1 1 calc R . . C25 C 0.6989(3) 0.6116(4) 0.3033(2) 0.0186(8) Uani 1 1 d . . . H25 H 0.6678 0.6327 0.2503 0.022 Uiso 1 1 calc R . . C26 C 0.6760(3) 0.4722(4) 0.3391(2) 0.0153(7) Uani 1 1 d . . . H26 H 0.6273 0.3982 0.31 0.018 Uiso 1 1 calc R . . C111 C 0.8682(3) 0.2096(4) 0.6847(2) 0.0121(6) Uani 1 1 d . . . C112 C 0.8971(3) 0.0626(4) 0.6582(2) 0.0140(7) Uani 1 1 d . . . H112 H 0.9109 0.0474 0.6048 0.017 Uiso 1 1 calc R . . C113 C 0.9054(3) -0.0623(4) 0.7111(2) 0.0164(7) Uani 1 1 d . . . H113 H 0.923 -0.1647 0.6934 0.02 Uiso 1 1 calc R . . C114 C 0.8881(3) -0.0397(4) 0.7897(2) 0.0162(7) Uani 1 1 d . . . H114 H 0.8948 -0.126 0.8255 0.019 Uiso 1 1 calc R . . C115 C 0.8612(3) 0.1094(4) 0.8156(2) 0.0152(7) Uani 1 1 d . . . H115 H 0.8497 0.1253 0.8693 0.018 Uiso 1 1 calc R . . C116 C 0.8511(3) 0.2352(4) 0.7631(2) 0.0151(7) Uani 1 1 d . . . H116 H 0.8327 0.3375 0.7805 0.018 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 0.00968(6) 0.01115(7) 0.00833(6) -0.00046(5) 0.00156(5) -0.00114(5) C1 0.0138(15) 0.0130(16) 0.0114(15) 0.0007(12) 0.0022(13) 0.0017(12) O1 0.0258(14) 0.0257(15) 0.0211(14) -0.0070(12) -0.0059(12) 0.0011(12) C2 0.0123(15) 0.0189(18) 0.0136(16) -0.0020(14) -0.0006(13) -0.0046(13) O2 0.0330(16) 0.0230(15) 0.0193(14) 0.0072(11) 0.0006(13) -0.0112(12) C3 0.0167(16) 0.0172(17) 0.0122(15) 0.0004(13) 0.0000(14) -0.0069(14) O3 0.0191(13) 0.0269(15) 0.0225(14) -0.0057(12) 0.0058(12) 0.0013(11) Br4 0.01320(15) 0.01475(16) 0.01552(16) -0.00094(13) 0.00479(13) -0.00009(12) N11 0.0147(13) 0.0128(14) 0.0100(13) 0.0005(11) 0.0027(11) -0.0020(11) C12 0.0110(14) 0.0115(15) 0.0112(15) -0.0004(12) 0.0041(13) 0.0000(12) N13 0.0149(13) 0.0126(14) 0.0079(13) -0.0006(10) 0.0009(11) -0.0010(10) C14 0.0153(16) 0.0157(17) 0.0183(18) -0.0013(14) 0.0007(15) -0.0063(13) C15 0.0150(16) 0.0161(17) 0.0159(17) -0.0034(14) -0.0011(14) -0.0049(13) N21 0.0129(13) 0.0133(14) 0.0097(13) 0.0004(11) 0.0047(11) 0.0024(11) C22 0.0129(15) 0.0142(16) 0.0097(14) 0.0006(13) 0.0050(13) 0.0023(13) C23 0.0186(17) 0.0155(18) 0.0177(17) 0.0000(14) 0.0053(15) -0.0018(13) C24 0.026(2) 0.0160(18) 0.0182(18) 0.0060(15) 0.0068(16) 0.0023(15) C25 0.0227(19) 0.0211(19) 0.0123(16) 0.0047(14) 0.0034(15) 0.0016(15) C26 0.0171(16) 0.0167(17) 0.0122(16) 0.0011(13) 0.0020(14) 0.0021(13) C111 0.0106(14) 0.0140(16) 0.0116(15) -0.0008(13) 0.0008(13) -0.0018(12) C112 0.0115(15) 0.0177(17) 0.0132(16) -0.0026(13) 0.0029(13) 0.0005(13) C113 0.0161(16) 0.0171(18) 0.0156(17) -0.0009(14) 0.0000(14) 0.0015(13) C114 0.0152(16) 0.0179(18) 0.0146(17) 0.0042(14) -0.0017(14) -0.0019(14) C115 0.0171(17) 0.0199(18) 0.0087(15) 0.0008(13) 0.0020(13) -0.0006(14) C116 0.0152(16) 0.0179(17) 0.0120(15) -0.0035(13) 0.0008(14) 0.0029(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C3 1.917(4) . ? Re1 C2 1.923(4) . ? Re1 C1 1.957(3) . ? Re1 C12 2.145(3) . ? Re1 N21 2.210(3) . ? Re1 Br4 2.6255(4) . ? C1 O1 1.141(4) . ? C2 O2 1.149(4) . ? C3 O3 1.145(4) . ? N11 C12 1.351(4) . ? N11 C15 1.401(4) . ? N11 C111 1.446(4) . ? C12 N13 1.376(4) . ? N13 C14 1.391(4) . ? N13 C22 1.403(4) . ? C14 C15 1.339(5) . ? C14 H14 0.95 . ? C15 H15 0.95 . ? N21 C22 1.346(4) . ? N21 C26 1.352(4) . ? C22 C23 1.390(5) . ? C23 C24 1.389(5) . ? C23 H23 0.95 . ? C24 C25 1.387(5) . ? C24 H24 0.95 . ? C25 C26 1.371(5) . ? C25 H25 0.95 . ? C26 H26 0.95 . ? C111 C112 1.383(5) . ? C111 C116 1.388(5) . ? C112 C113 1.386(5) . ? C112 H112 0.95 . ? C113 C114 1.389(5) . ? C113 H113 0.95 . ? C114 C115 1.389(5) . ? C114 H114 0.95 . ? C115 C116 1.389(5) . ? C115 H115 0.95 . ? C116 H116 0.95 . ? 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 C3 Re1 C2 89.42(15) . . ? C3 Re1 C1 92.06(14) . . ? C2 Re1 C1 87.94(14) . . ? C3 Re1 C12 96.25(13) . . ? C2 Re1 C12 100.14(13) . . ? C1 Re1 C12 168.43(14) . . ? C3 Re1 N21 93.24(13) . . ? C2 Re1 N21 174.42(12) . . ? C1 Re1 N21 96.86(12) . . ? C12 Re1 N21 74.70(12) . . ? C3 Re1 Br4 177.81(11) . . ? C2 Re1 Br4 92.66(11) . . ? C1 Re1 Br4 87.32(10) . . ? C12 Re1 Br4 84.07(9) . . ? N21 Re1 Br4 84.75(7) . . ? O1 C1 Re1 177.0(3) . . ? O2 C2 Re1 179.1(3) . . ? O3 C3 Re1 178.2(3) . . ? C12 N11 C15 111.5(3) . . ? C12 N11 C111 126.5(3) . . ? C15 N11 C111 122.0(3) . . ? N11 C12 N13 103.5(3) . . ? N11 C12 Re1 142.0(3) . . ? N13 C12 Re1 114.3(2) . . ? C12 N13 C14 111.7(3) . . ? C12 N13 C22 120.5(3) . . ? C14 N13 C22 127.8(3) . . ? C15 C14 N13 106.3(3) . . ? C15 C14 H14 126.9 . . ? N13 C14 H14 126.9 . . ? C14 C15 N11 107.1(3) . . ? C14 C15 H15 126.5 . . ? N11 C15 H15 126.5 . . ? C22 N21 C26 117.3(3) . . ? C22 N21 Re1 116.8(2) . . ? C26 N21 Re1 125.9(2) . . ? N21 C22 C23 123.9(3) . . ? N21 C22 N13 113.8(3) . . ? C23 C22 N13 122.4(3) . . ? C24 C23 C22 117.0(3) . . ? C24 C23 H23 121.5 . . ? C22 C23 H23 121.5 . . ? C25 C24 C23 120.1(3) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C26 C25 C24 118.6(3) . . ? C26 C25 H25 120.7 . . ? C24 C25 H25 120.7 . . ? N21 C26 C25 123.0(3) . . ? N21 C26 H26 118.5 . . ? C25 C26 H26 118.5 . . ? C112 C111 C116 121.6(3) . . ? C112 C111 N11 119.2(3) . . ? C116 C111 N11 119.2(3) . . ? C111 C112 C113 118.6(3) . . ? C111 C112 H112 120.7 . . ? C113 C112 H112 120.7 . . ? C112 C113 C114 120.8(3) . . ? C112 C113 H113 119.6 . . ? C114 C113 H113 119.6 . . ? C115 C114 C113 119.8(3) . . ? C115 C114 H114 120.1 . . ? C113 C114 H114 120.1 . . ? C114 C115 C116 120.1(3) . . ? C114 C115 H115 120 . . ? C116 C115 H115 120 . . ? C111 C116 C115 119.2(3) . . ? C111 C116 H116 120.4 . . ? C115 C116 H116 120.4 . . ? _database_code_depnum_ccdc_archive 'CCDC 934465' ####################################################################### # # 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_mxm86 #TrackingRef 'web_deposit_cif_file_0_BrianSkelton_1366251824.mxm86.cif' _audit_creation_date 2013-04-18T09:41:22-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C21 H13 Cl N3 O3 Re' _chemical_formula_moiety 'C21 H13 Cl N3 O3 Re' _chemical_formula_weight 576.99 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' 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 10.6269(3) _cell_length_b 11.7796(3) _cell_length_c 30.7456(5) _cell_angle_alpha 90 _cell_angle_beta 90.507(2) _cell_angle_gamma 90 _cell_volume 3848.60(16) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7264 _cell_measurement_theta_min 3.23 _cell_measurement_theta_max 30.592 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description slab _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.992 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2208 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -2 -3 1 0.0623 2 2 -3 0.0546 1 -1 -2 0.0332 -2 1 2 0.0269 0 0 -1 0.0429 0 0 1 0.0411 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 6.482 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_absorpt_correction_T_min 0.496 _exptl_absorpt_correction_T_max 0.723 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 16.0009 _diffrn_orient_matrix_ub_11 -0.0632905 _diffrn_orient_matrix_ub_12 0.0173275 _diffrn_orient_matrix_ub_13 0.003009 _diffrn_orient_matrix_ub_21 0.0208671 _diffrn_orient_matrix_ub_22 0.0552304 _diffrn_orient_matrix_ub_23 0.0057151 _diffrn_orient_matrix_ub_31 -0.0037985 _diffrn_orient_matrix_ub_32 0.0166022 _diffrn_orient_matrix_ub_33 -0.0221463 _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur diffractometer' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_unetI/netI 0.0426 _diffrn_reflns_number 25394 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 31.45 _diffrn_reflns_theta_full 31 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.963 _reflns_number_total 6146 _reflns_number_gt 5348 _reflns_threshold_expression I>2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'OrtepII (Johnson, C. K. (1976)' _computing_publication_material 'WinGX Farrugia, L. J. (1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The phenyl ring was modelled as being disordered over two sets of sites with occupancies refined to 0.688(13) and its complement. Geometries and displacement parameters of the minor component were restrained to reasonable values. ; _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^)+(0.0150P)^2^+17.1588P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 6146 _refine_ls_number_parameters 311 _refine_ls_number_restraints 78 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.0725 _refine_ls_wR_factor_gt 0.0694 _refine_ls_goodness_of_fit_ref 1.129 _refine_ls_restrained_S_all 1.133 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.643 _refine_diff_density_min -0.794 _refine_diff_density_rms 0.144 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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 7.231 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.261336(17) 0.526030(15) 0.627365(5) 0.02704(6) Uani 1 1 d . A . Cl1 Cl 0.46250(12) 0.60960(10) 0.60255(4) 0.0389(3) Uani 1 1 d . . . C101 C 0.3043(4) 0.3740(4) 0.60739(13) 0.0294(9) Uani 1 1 d . . . O101 O 0.3261(4) 0.2810(3) 0.59904(11) 0.0442(9) Uani 1 1 d . . . C201 C 0.3338(5) 0.4809(4) 0.68166(14) 0.0335(9) Uani 1 1 d . . . O201 O 0.3790(4) 0.4541(3) 0.71409(10) 0.0477(9) Uani 1 1 d . . . C301 C 0.0944(5) 0.4675(4) 0.64428(13) 0.0347(10) Uani 1 1 d . . . O301 O 0.0073(4) 0.4317(4) 0.65422(13) 0.0569(10) Uani 1 1 d . . . N1 N 0.2001(4) 0.7518(3) 0.68469(11) 0.0339(9) Uani 1 1 d . . . C2 C 0.2070(4) 0.6904(4) 0.64792(13) 0.0285(9) Uani 1 1 d . A . N3 N 0.1565(4) 0.7598(3) 0.61695(11) 0.0304(8) Uani 1 1 d . . . C4 C 0.1208(5) 0.8635(4) 0.63435(15) 0.0401(12) Uani 1 1 d . A . H4 H 0.0844 0.9257 0.6191 0.048 Uiso 1 1 calc R . . C5 C 0.1477(5) 0.8583(4) 0.67683(16) 0.0429(12) Uani 1 1 d . A . H5 H 0.1338 0.9163 0.6977 0.051 Uiso 1 1 calc R . . C11 C 0.2290(12) 0.708(2) 0.7285(6) 0.032(2) Uani 0.688(13) 1 d PU A 1 C12 C 0.1636(8) 0.6198(9) 0.7445(2) 0.047(2) Uani 0.688(13) 1 d PU A 1 H12 H 0.1019 0.5829 0.727 0.057 Uiso 0.688(13) 1 calc PR A 1 C13 C 0.1870(9) 0.5831(10) 0.7866(2) 0.054(3) Uani 0.688(13) 1 d PU A 1 H13 H 0.142 0.5204 0.7981 0.064 Uiso 0.688(13) 1 calc PR A 1 C14 C 0.2748(15) 0.6374(13) 0.8115(5) 0.056(4) Uani 0.688(13) 1 d PU A 1 H14 H 0.2889 0.6139 0.8407 0.068 Uiso 0.688(13) 1 calc PR A 1 C15 C 0.3414(14) 0.7238(9) 0.7951(4) 0.062(3) Uani 0.688(13) 1 d PU A 1 H15 H 0.4041 0.759 0.8127 0.074 Uiso 0.688(13) 1 calc PR A 1 C16 C 0.3208(11) 0.7636(8) 0.7525(3) 0.053(3) Uani 0.688(13) 1 d PU A 1 H16 H 0.3674 0.8251 0.7408 0.064 Uiso 0.688(13) 1 calc PR A 1 C11' C 0.237(2) 0.722(6) 0.7261(14) 0.032(2) Uani 0.312(13) 1 d PDU A 2 C12' C 0.144(2) 0.693(2) 0.7554(6) 0.053(5) Uani 0.312(13) 1 d PDU A 2 H12' H 0.058 0.692 0.7466 0.064 Uiso 0.312(13) 1 calc PR A 2 C13' C 0.1780(18) 0.665(2) 0.7977(6) 0.058(6) Uani 0.312(13) 1 d PDU A 2 H13' H 0.1143 0.6466 0.818 0.07 Uiso 0.312(13) 1 calc PR A 2 C14' C 0.3042(18) 0.663(2) 0.8110(9) 0.032(5) Uani 0.312(13) 1 d PDU A 2 H14' H 0.3267 0.6382 0.8395 0.039 Uiso 0.312(13) 1 calc PR A 2 C15' C 0.3940(18) 0.696(2) 0.7826(6) 0.049(5) Uani 0.312(13) 1 d PDU A 2 H15' H 0.4792 0.7031 0.7919 0.059 Uiso 0.312(13) 1 calc PR A 2 C16' C 0.3606(19) 0.719(2) 0.7399(6) 0.053(5) Uani 0.312(13) 1 d PDU A 2 H16' H 0.4251 0.734 0.7195 0.064 Uiso 0.312(13) 1 calc PR A 2 N21 N 0.1835(3) 0.6154(3) 0.56723(10) 0.0280(7) Uani 1 1 d . . . C22 C 0.1421(4) 0.7197(4) 0.57406(13) 0.0280(9) Uani 1 1 d . A . C23 C 0.0855(4) 0.7904(4) 0.54251(14) 0.0326(10) Uani 1 1 d . . . H23 H 0.0587 0.865 0.5497 0.039 Uiso 1 1 calc R A . C24 C 0.0702(4) 0.7488(4) 0.50157(14) 0.0325(10) Uani 1 1 d . A . H24 H 0.0297 0.7932 0.4798 0.039 Uiso 1 1 calc R . . C24A C 0.1149(4) 0.6393(4) 0.49173(12) 0.0289(9) Uani 1 1 d . . . C25 C 0.1059(5) 0.5946(4) 0.44905(14) 0.0364(11) Uani 1 1 d . A . H25 H 0.0646 0.6372 0.4269 0.044 Uiso 1 1 calc R . . C26 C 0.1560(5) 0.4908(4) 0.43937(14) 0.0387(11) Uani 1 1 d . . . H26 H 0.1486 0.461 0.4107 0.046 Uiso 1 1 calc R A . C27 C 0.2186(5) 0.4281(5) 0.47209(14) 0.0421(12) Uani 1 1 d . A . H27 H 0.2553 0.3569 0.4653 0.05 Uiso 1 1 calc R . . C28 C 0.2268(5) 0.4695(5) 0.51376(14) 0.0389(11) Uani 1 1 d . . . H28 H 0.2689 0.4259 0.5354 0.047 Uiso 1 1 calc R A . C28A C 0.1745(4) 0.5743(4) 0.52498(13) 0.0279(8) Uani 1 1 d . A . 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 0.03576(9) 0.02773(9) 0.01756(8) -0.00139(7) -0.00397(6) 0.01036(7) Cl1 0.0458(7) 0.0361(6) 0.0345(6) 0.0057(5) -0.0079(5) 0.0070(5) C101 0.036(2) 0.034(2) 0.0188(18) 0.0003(16) -0.0007(16) 0.0063(19) O101 0.069(3) 0.0309(18) 0.0331(18) -0.0049(14) 0.0003(16) 0.0085(17) C201 0.043(2) 0.031(2) 0.026(2) -0.0030(18) -0.0017(18) 0.009(2) O201 0.066(3) 0.050(2) 0.0262(16) 0.0031(15) -0.0123(16) 0.0154(18) C301 0.053(3) 0.036(2) 0.0151(18) -0.0022(17) -0.0087(18) 0.003(2) O301 0.059(3) 0.070(3) 0.042(2) -0.003(2) -0.0041(19) 0.002(2) N1 0.046(2) 0.034(2) 0.0207(17) -0.0058(15) -0.0079(15) 0.0172(18) C2 0.030(2) 0.033(2) 0.0230(19) -0.0022(16) -0.0030(16) 0.0098(18) N3 0.035(2) 0.0325(19) 0.0230(17) -0.0037(14) -0.0071(14) 0.0128(16) C4 0.056(3) 0.029(2) 0.035(2) -0.0035(19) -0.011(2) 0.021(2) C5 0.059(3) 0.035(3) 0.035(2) -0.012(2) -0.010(2) 0.021(2) C11 0.044(3) 0.033(7) 0.020(3) -0.006(3) -0.005(2) 0.014(3) C12 0.042(4) 0.070(6) 0.031(4) 0.000(4) 0.000(3) 0.011(4) C13 0.053(5) 0.079(6) 0.029(4) 0.008(4) 0.005(3) 0.013(4) C14 0.069(7) 0.063(8) 0.037(5) -0.002(5) -0.010(5) 0.018(6) C15 0.086(7) 0.055(5) 0.043(5) -0.013(4) -0.031(5) 0.009(5) C16 0.079(6) 0.037(4) 0.043(4) -0.004(3) -0.028(4) 0.004(4) C11' 0.044(3) 0.033(7) 0.020(3) -0.006(3) -0.005(2) 0.014(3) C12' 0.046(8) 0.064(9) 0.050(8) 0.013(7) -0.011(7) -0.008(7) C13' 0.052(9) 0.073(10) 0.050(8) 0.015(7) -0.005(7) -0.015(8) C14' 0.039(8) 0.031(8) 0.025(8) -0.003(6) -0.012(6) -0.005(7) C15' 0.037(8) 0.073(10) 0.038(8) 0.002(7) -0.005(6) 0.010(7) C16' 0.046(8) 0.073(10) 0.041(8) 0.004(7) 0.007(6) 0.019(7) N21 0.0330(19) 0.0324(19) 0.0184(15) -0.0003(14) -0.0055(13) 0.0084(15) C22 0.030(2) 0.033(2) 0.0206(18) 0.0007(16) -0.0045(16) 0.0054(17) C23 0.037(2) 0.035(2) 0.026(2) 0.0044(17) -0.0046(18) 0.0069(19) C24 0.033(2) 0.041(3) 0.024(2) 0.0090(18) -0.0057(17) 0.0073(19) C24A 0.027(2) 0.043(3) 0.0167(18) 0.0017(17) -0.0031(15) 0.0006(18) C25 0.039(3) 0.049(3) 0.021(2) 0.0038(19) -0.0069(18) -0.005(2) C26 0.047(3) 0.050(3) 0.0188(19) -0.0050(19) -0.0040(18) -0.002(2) C27 0.058(3) 0.044(3) 0.024(2) -0.009(2) -0.004(2) 0.009(2) C28 0.050(3) 0.043(3) 0.023(2) -0.003(2) -0.0071(19) 0.012(2) C28A 0.027(2) 0.035(2) 0.0213(18) 0.0011(17) -0.0024(15) 0.0015(18) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C201 1.908(4) . ? Re1 C101 1.949(5) . ? Re1 C301 1.977(6) . ? Re1 C2 2.119(4) . ? Re1 N21 2.277(3) . ? Re1 Cl1 2.4799(13) . ? C101 O101 1.150(5) . ? C201 O201 1.147(5) . ? C301 O301 1.064(6) . ? N1 C2 1.345(5) . ? N1 C11' 1.37(4) . ? N1 C5 1.392(6) . ? N1 C11 1.472(17) . ? C2 N3 1.362(5) . ? N3 C4 1.387(6) . ? N3 C22 1.408(5) . ? C4 C5 1.336(7) . ? C4 H4 0.95 . ? C5 H5 0.95 . ? C11 C12 1.35(2) . ? C11 C16 1.38(2) . ? C12 C13 1.386(11) . ? C12 H12 0.95 . ? C13 C14 1.360(18) . ? C13 H13 0.95 . ? C14 C15 1.341(18) . ? C14 H14 0.95 . ? C15 C16 1.408(13) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C11' C16' 1.38(2) . ? C11' C12' 1.39(2) . ? C12' C13' 1.385(16) . ? C12' H12' 0.95 . ? C13' C14' 1.399(18) . ? C13' H13' 0.95 . ? C14' C15' 1.359(18) . ? C14' H14' 0.95 . ? C15' C16' 1.382(16) . ? C15' H15' 0.95 . ? C16' H16' 0.95 . ? N21 C22 1.323(6) . ? N21 C28A 1.389(5) . ? C22 C23 1.409(6) . ? C23 C24 1.359(6) . ? C23 H23 0.95 . ? C24 C24A 1.408(7) . ? C24 H24 0.95 . ? C24A C25 1.417(6) . ? C24A C28A 1.422(6) . ? C25 C26 1.367(7) . ? C25 H25 0.95 . ? C26 C27 1.410(7) . ? C26 H26 0.95 . ? C27 C28 1.373(6) . ? C27 H27 0.95 . ? C28 C28A 1.399(7) . ? C28 H28 0.95 . ? 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 C201 Re1 C101 85.75(18) . . ? C201 Re1 C301 91.65(19) . . ? C101 Re1 C301 88.6(2) . . ? C201 Re1 C2 95.88(17) . . ? C101 Re1 C2 177.60(18) . . ? C301 Re1 C2 89.60(19) . . ? C201 Re1 N21 168.61(17) . . ? C101 Re1 N21 104.68(15) . . ? C301 Re1 N21 93.14(16) . . ? C2 Re1 N21 73.84(14) . . ? C201 Re1 Cl1 92.14(16) . . ? C101 Re1 Cl1 93.60(14) . . ? C301 Re1 Cl1 175.74(13) . . ? C2 Re1 Cl1 88.09(13) . . ? N21 Re1 Cl1 82.78(10) . . ? O101 C101 Re1 174.1(4) . . ? O201 C201 Re1 179.0(5) . . ? O301 C301 Re1 176.6(5) . . ? C2 N1 C11' 129(3) . . ? C2 N1 C5 111.3(4) . . ? C11' N1 C5 120(3) . . ? C2 N1 C11 124.7(13) . . ? C5 N1 C11 123.6(12) . . ? N1 C2 N3 103.9(4) . . ? N1 C2 Re1 139.4(3) . . ? N3 C2 Re1 116.6(3) . . ? C2 N3 C4 111.5(3) . . ? C2 N3 C22 119.5(4) . . ? C4 N3 C22 128.9(4) . . ? C5 C4 N3 106.2(4) . . ? C5 C4 H4 126.9 . . ? N3 C4 H4 126.9 . . ? C4 C5 N1 107.0(4) . . ? C4 C5 H5 126.5 . . ? N1 C5 H5 126.5 . . ? C12 C11 C16 122.4(13) . . ? C12 C11 N1 120.0(15) . . ? C16 C11 N1 117.5(15) . . ? C11 C12 C13 119.5(12) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C14 C13 C12 119.7(11) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C15 C14 C13 120.5(13) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 121.6(11) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C11 C16 C15 116.2(12) . . ? C11 C16 H16 121.9 . . ? C15 C16 H16 121.9 . . ? N1 C11' C16' 124(2) . . ? N1 C11' C12' 118(2) . . ? C16' C11' C12' 118(3) . . ? C13' C12' C11' 119(2) . . ? C13' C12' H12' 120.4 . . ? C11' C12' H12' 120.4 . . ? C12' C13' C14' 121(2) . . ? C12' C13' H13' 119.3 . . ? C14' C13' H13' 119.3 . . ? C15' C14' C13' 119(2) . . ? C15' C14' H14' 120.6 . . ? C13' C14' H14' 120.6 . . ? C14' C15' C16' 119(2) . . ? C14' C15' H15' 120.3 . . ? C16' C15' H15' 120.3 . . ? C11' C16' C15' 122(2) . . ? C11' C16' H16' 118.8 . . ? C15' C16' H16' 118.8 . . ? C22 N21 C28A 116.8(3) . . ? C22 N21 Re1 114.8(3) . . ? C28A N21 Re1 128.3(3) . . ? N21 C22 N3 115.3(3) . . ? N21 C22 C23 125.5(4) . . ? N3 C22 C23 119.3(4) . . ? C24 C23 C22 118.1(4) . . ? C24 C23 H23 120.9 . . ? C22 C23 H23 120.9 . . ? C23 C24 C24A 119.4(4) . . ? C23 C24 H24 120.3 . . ? C24A C24 H24 120.3 . . ? C24 C24A C25 121.3(4) . . ? C24 C24A C28A 119.2(4) . . ? C25 C24A C28A 119.4(4) . . ? C26 C25 C24A 120.8(4) . . ? C26 C25 H25 119.6 . . ? C24A C25 H25 119.6 . . ? C25 C26 C27 119.7(4) . . ? C25 C26 H26 120.2 . . ? C27 C26 H26 120.2 . . ? C28 C27 C26 120.4(5) . . ? C28 C27 H27 119.8 . . ? C26 C27 H27 119.8 . . ? C27 C28 C28A 121.4(4) . . ? C27 C28 H28 119.3 . . ? C28A C28 H28 119.3 . . ? N21 C28A C28 120.9(4) . . ? N21 C28A C24A 120.8(4) . . ? C28 C28A C24A 118.3(4) . . ? #===END _database_code_depnum_ccdc_archive 'CCDC 934669' ####################################################################### # # 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_mxm67 #TrackingRef 'web_deposit_cif_file_2_BrianSkelton_1366179046.mxm67.cif' _audit_creation_date 2012-08-03T10:38:13-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C21 H13 Br N3 O3 Re' _chemical_formula_moiety 'C21 H13 Br N3 O3 Re' _chemical_formula_weight 621.45 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-c 2yc' 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 10.6245(2) _cell_length_b 11.8726(2) _cell_length_c 30.9574(4) _cell_angle_alpha 90 _cell_angle_beta 90.701(2) _cell_angle_gamma 90 _cell_volume 3904.69(11) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 14319 _cell_measurement_theta_min 2.8731 _cell_measurement_theta_max 37.6286 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 2.114 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2352 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 -1 -2 0.1068 1 1 2 0.1138 -1 1 -2 0.1086 1 -1 2 0.1104 0 0 -1 0.0277 0 0 1 0.0277 -1 -1 6 0.0811 1 1 -5 0.0774 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 8.299 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_absorpt_correction_T_min 0.169 _exptl_absorpt_correction_T_max 0.653 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 16.0009 _diffrn_orient_matrix_ub_11 0.0534419 _diffrn_orient_matrix_ub_12 0.0345957 _diffrn_orient_matrix_ub_13 0.0037139 _diffrn_orient_matrix_ub_21 0.037954 _diffrn_orient_matrix_ub_22 -0.0390958 _diffrn_orient_matrix_ub_23 -0.011257 _diffrn_orient_matrix_ub_31 -0.0126877 _diffrn_orient_matrix_ub_32 0.0290097 _diffrn_orient_matrix_ub_33 -0.0196161 _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur diffractometer' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_unetI/netI 0.0315 _diffrn_reflns_number 56772 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -49 _diffrn_reflns_limit_l_max 49 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 35 _diffrn_reflns_theta_full 35 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 8586 _reflns_number_gt 7515 _reflns_threshold_expression I>2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'OrtepII (Johnson, C. K. (1976)' _computing_publication_material 'WinGX Farrugia, L. J. (1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The phenyl ring was modelled as being disordered over two sets of sites with occupancies refined to 0.639(9) and its complement. Geometries of the minor component were restrained to ideal values. Displacement parameters for this group were restrained to reasonable values. ; _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^)+(0.0347P)^2^+19.8111P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 8586 _refine_ls_number_parameters 317 _refine_ls_number_restraints 90 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0884 _refine_ls_wR_factor_gt 0.085 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.111 _refine_ls_shift/su_max 0.049 _refine_ls_shift/su_mean 0.003 _refine_diff_density_max 2.478 _refine_diff_density_min -1.996 _refine_diff_density_rms 0.181 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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 7.231 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.259469(14) 0.480122(11) 0.372469(4) 0.02343(4) Uani 1 1 d . A . Br1 Br 0.47235(4) 0.38834(3) 0.398063(13) 0.03137(8) Uani 1 1 d . . . C101 C 0.3060(4) 0.6307(3) 0.39261(12) 0.0274(6) Uani 1 1 d . . . O101 O 0.3320(3) 0.7223(2) 0.40121(10) 0.0372(7) Uani 1 1 d . . . C201 C 0.3308(4) 0.5256(3) 0.31878(12) 0.0315(8) Uani 1 1 d . . . O201 O 0.3774(4) 0.5508(3) 0.28683(10) 0.0466(9) Uani 1 1 d . . . C301 C 0.0854(5) 0.5423(4) 0.35504(12) 0.0342(8) Uani 1 1 d U . . O301 O 0.0084(4) 0.5756(4) 0.34705(12) 0.0492(9) Uani 1 1 d U . . N1 N 0.1990(4) 0.2557(3) 0.31507(11) 0.0355(8) Uani 1 1 d . . . C2 C 0.2054(4) 0.3174(3) 0.35170(11) 0.0275(7) Uani 1 1 d . A . N3 N 0.1574(3) 0.2473(3) 0.38238(10) 0.0291(6) Uani 1 1 d . . . C4 C 0.1245(5) 0.1424(4) 0.36506(14) 0.0412(11) Uani 1 1 d . A . H4 H 0.0917 0.0795 0.3802 0.049 Uiso 1 1 calc R . . C5 C 0.1487(6) 0.1490(4) 0.32300(15) 0.0476(13) Uani 1 1 d . A . H5 H 0.1344 0.0915 0.3022 0.057 Uiso 1 1 calc R . . C11 C 0.2229(11) 0.3014(10) 0.2711(4) 0.030(2) Uani 0.639(9) 1 d PU A 1 C12 C 0.1639(7) 0.3887(8) 0.2563(2) 0.0411(16) Uani 0.639(9) 1 d PU A 1 H12 H 0.1056 0.4276 0.2739 0.049 Uiso 0.639(9) 1 calc PR A 1 C13 C 0.1866(8) 0.4251(9) 0.2144(3) 0.0486(19) Uani 0.639(9) 1 d PU A 1 H13 H 0.1421 0.4884 0.2033 0.058 Uiso 0.639(9) 1 calc PR A 1 C14 C 0.2698(10) 0.3725(9) 0.1895(3) 0.045(2) Uani 0.639(9) 1 d PU A 1 H14 H 0.2832 0.3978 0.1608 0.054 Uiso 0.639(9) 1 calc PR A 1 C15 C 0.3354(10) 0.2825(8) 0.2053(3) 0.052(2) Uani 0.639(9) 1 d PU A 1 H15 H 0.3954 0.246 0.1876 0.062 Uiso 0.639(9) 1 calc PR A 1 C16 C 0.3157(9) 0.2433(7) 0.2472(3) 0.0465(18) Uani 0.639(9) 1 d PU A 1 H16 H 0.3615 0.1816 0.259 0.056 Uiso 0.639(9) 1 calc PR A 1 C11' C 0.2413(14) 0.2823(14) 0.2742(6) 0.021(3) Uani 0.361(9) 1 d PDU A 2 C12' C 0.1415(15) 0.3067(16) 0.2439(5) 0.056(4) Uani 0.361(9) 1 d PDU A 2 H12' H 0.0563 0.3042 0.2528 0.068 Uiso 0.361(9) 1 calc PR A 2 C13' C 0.1713(15) 0.3340(18) 0.2013(6) 0.063(5) Uani 0.361(9) 1 d PDU A 2 H13' H 0.1066 0.3475 0.1805 0.076 Uiso 0.361(9) 1 calc PR A 2 C14' C 0.2972(10) 0.3412(10) 0.1901(4) 0.023(2) Uani 0.361(9) 1 d PDU A 2 H14' H 0.3188 0.3672 0.1621 0.027 Uiso 0.361(9) 1 calc PR A 2 C15' C 0.3891(13) 0.3119(14) 0.2183(4) 0.043(3) Uani 0.361(9) 1 d PDU A 2 H15' H 0.4737 0.3065 0.209 0.052 Uiso 0.361(9) 1 calc PR A 2 C16' C 0.3597(16) 0.2895(19) 0.2613(5) 0.062(4) Uani 0.361(9) 1 d PDU A 2 H16' H 0.426 0.2792 0.2818 0.074 Uiso 0.361(9) 1 calc PR A 2 N21 N 0.1836(3) 0.3916(3) 0.43191(9) 0.0236(5) Uani 1 1 d . . . C22 C 0.1440(3) 0.2865(3) 0.42479(11) 0.0247(6) Uani 1 1 d . A . C23 C 0.0892(4) 0.2153(3) 0.45594(12) 0.0282(7) Uani 1 1 d . . . H23 H 0.0642 0.1407 0.4488 0.034 Uiso 1 1 calc R A . C24 C 0.0735(4) 0.2569(3) 0.49647(11) 0.0280(7) Uani 1 1 d . A . H24 H 0.0332 0.2128 0.5178 0.034 Uiso 1 1 calc R . . C24A C 0.1174(3) 0.3666(3) 0.50659(11) 0.0248(6) Uani 1 1 d . . . C25 C 0.1087(4) 0.4109(4) 0.54922(11) 0.0292(7) Uani 1 1 d . A . H25 H 0.0685 0.3682 0.571 0.035 Uiso 1 1 calc R . . C26 C 0.1580(4) 0.5145(4) 0.55902(12) 0.0317(7) Uani 1 1 d . . . H26 H 0.1512 0.544 0.5874 0.038 Uiso 1 1 calc R A . C27 C 0.2189(4) 0.5772(4) 0.52678(12) 0.0328(8) Uani 1 1 d . A . H27 H 0.255 0.6482 0.5338 0.039 Uiso 1 1 calc R . . C28 C 0.2267(4) 0.5371(3) 0.48527(12) 0.0307(7) Uani 1 1 d . . . H28 H 0.2672 0.5811 0.4639 0.037 Uiso 1 1 calc R A . C28A C 0.1756(3) 0.4316(3) 0.47397(10) 0.0232(6) Uani 1 1 d . A . 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 0.03220(7) 0.02280(6) 0.01535(6) -0.00162(4) 0.00260(4) -0.00932(5) Br1 0.03597(19) 0.02845(16) 0.02980(17) 0.00364(13) 0.00441(14) -0.00686(14) C101 0.0371(18) 0.0240(14) 0.0211(14) 0.0006(11) 0.0011(12) -0.0057(13) O101 0.058(2) 0.0242(12) 0.0294(14) -0.0039(10) 0.0006(13) -0.0084(12) C201 0.047(2) 0.0263(16) 0.0211(14) -0.0019(12) 0.0061(14) -0.0095(15) O201 0.074(3) 0.0416(17) 0.0245(14) -0.0009(12) 0.0172(15) -0.0197(17) C301 0.058(2) 0.0292(15) 0.0156(12) -0.0018(11) 0.0113(14) -0.0013(15) O301 0.0547(19) 0.0573(19) 0.0357(15) -0.0069(14) 0.0075(14) -0.0134(16) N1 0.053(2) 0.0330(16) 0.0211(13) -0.0099(12) 0.0106(13) -0.0234(15) C2 0.0368(18) 0.0290(15) 0.0168(13) -0.0034(11) 0.0068(12) -0.0127(14) N3 0.0408(17) 0.0275(14) 0.0193(12) -0.0040(10) 0.0075(11) -0.0155(12) C4 0.062(3) 0.0327(19) 0.0291(18) -0.0089(15) 0.0123(18) -0.027(2) C5 0.077(4) 0.037(2) 0.0291(19) -0.0145(17) 0.017(2) -0.034(2) C11 0.039(3) 0.030(4) 0.022(3) -0.003(3) 0.005(2) -0.007(3) C12 0.037(3) 0.061(3) 0.026(2) 0.004(2) 0.001(2) -0.006(2) C13 0.045(3) 0.066(4) 0.035(3) 0.008(3) -0.003(2) -0.006(3) C14 0.050(4) 0.053(4) 0.032(3) -0.001(3) 0.002(3) -0.005(3) C15 0.064(4) 0.053(3) 0.040(3) -0.007(3) 0.016(3) -0.011(3) C16 0.062(4) 0.038(3) 0.039(3) -0.007(2) 0.017(3) -0.006(3) C11' 0.028(4) 0.016(4) 0.018(4) -0.002(3) 0.001(3) -0.004(3) C12' 0.052(5) 0.060(5) 0.057(5) 0.009(4) 0.012(4) 0.010(4) C13' 0.061(6) 0.068(6) 0.060(6) 0.010(4) 0.002(4) 0.006(4) C14' 0.027(3) 0.023(3) 0.018(3) -0.002(3) 0.007(3) 0.005(3) C15' 0.038(4) 0.054(4) 0.037(4) 0.006(3) 0.002(3) -0.008(3) C16' 0.058(5) 0.069(6) 0.057(5) 0.005(4) -0.003(4) -0.011(4) N21 0.0285(13) 0.0261(13) 0.0164(11) -0.0025(9) 0.0039(10) -0.0081(10) C22 0.0284(15) 0.0278(15) 0.0179(13) -0.0008(11) 0.0022(11) -0.0086(12) C23 0.0342(17) 0.0291(16) 0.0214(14) 0.0020(12) 0.0048(12) -0.0101(13) C24 0.0305(16) 0.0334(17) 0.0202(14) 0.0034(12) 0.0052(12) -0.0082(13) C24A 0.0251(14) 0.0325(16) 0.0167(12) 0.0010(11) 0.0025(11) -0.0021(12) C25 0.0312(17) 0.0384(19) 0.0181(13) 0.0004(13) 0.0056(12) -0.0011(14) C26 0.0388(19) 0.0384(19) 0.0179(13) -0.0042(13) 0.0034(13) 0.0003(16) C27 0.041(2) 0.0358(19) 0.0215(15) -0.0062(13) 0.0023(14) -0.0065(16) C28 0.042(2) 0.0330(18) 0.0176(13) -0.0036(12) 0.0031(13) -0.0101(15) C28A 0.0258(14) 0.0275(15) 0.0162(12) -0.0002(11) 0.0016(10) -0.0036(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C201 1.913(4) . ? Re1 C101 1.955(4) . ? Re1 C301 2.058(5) . ? Re1 C2 2.114(4) . ? Re1 N21 2.275(3) . ? Re1 Br1 2.6243(5) . ? C101 O101 1.153(5) . ? C201 O201 1.151(5) . ? C301 O301 0.939(6) . ? N1 C2 1.351(4) . ? N1 C11' 1.383(18) . ? N1 C5 1.398(5) . ? N1 C11 1.488(12) . ? C2 N3 1.366(4) . ? N3 C4 1.398(5) . ? N3 C22 1.402(4) . ? C4 C5 1.333(6) . ? C4 H4 0.95 . ? C5 H5 0.95 . ? C11 C12 1.292(14) . ? C11 C16 1.419(14) . ? C12 C13 1.394(10) . ? C12 H12 0.95 . ? C13 C14 1.335(14) . ? C13 H13 0.95 . ? C14 C15 1.364(15) . ? C14 H14 0.95 . ? C15 C16 1.398(12) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C11' C16' 1.327(16) . ? C11' C12' 1.436(16) . ? C12' C13' 1.398(16) . ? C12' H12' 0.95 . ? C13' C14' 1.389(15) . ? C13' H13' 0.95 . ? C14' C15' 1.348(14) . ? C14' H14' 0.95 . ? C15' C16' 1.398(15) . ? C15' H15' 0.95 . ? C16' H16' 0.95 . ? N21 C22 1.334(4) . ? N21 C28A 1.390(4) . ? C22 C23 1.413(5) . ? C23 C24 1.361(5) . ? C23 H23 0.95 . ? C24 C24A 1.417(5) . ? C24 H24 0.95 . ? C24A C28A 1.419(5) . ? C24A C25 1.424(5) . ? C25 C26 1.370(6) . ? C25 H25 0.95 . ? C26 C27 1.409(6) . ? C26 H26 0.95 . ? C27 C28 1.374(5) . ? C27 H27 0.95 . ? C28 C28A 1.407(5) . ? C28 H28 0.95 . ? 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 C201 Re1 C101 85.28(15) . . ? C201 Re1 C301 92.03(18) . . ? C101 Re1 C301 88.77(17) . . ? C201 Re1 C2 95.91(14) . . ? C101 Re1 C2 178.61(15) . . ? C301 Re1 C2 90.46(17) . . ? C201 Re1 N21 168.85(14) . . ? C101 Re1 N21 104.79(13) . . ? C301 Re1 N21 92.97(13) . . ? C2 Re1 N21 74.10(11) . . ? C201 Re1 Br1 91.74(14) . . ? C101 Re1 Br1 94.00(12) . . ? C301 Re1 Br1 175.50(11) . . ? C2 Re1 Br1 86.70(12) . . ? N21 Re1 Br1 82.90(8) . . ? O101 C101 Re1 174.6(3) . . ? O201 C201 Re1 177.6(5) . . ? O301 C301 Re1 176.1(5) . . ? C2 N1 C11' 129.1(8) . . ? C2 N1 C5 111.0(3) . . ? C11' N1 C5 119.7(8) . . ? C2 N1 C11 124.2(5) . . ? C5 N1 C11 124.1(5) . . ? N1 C2 N3 103.8(3) . . ? N1 C2 Re1 139.6(3) . . ? N3 C2 Re1 116.6(2) . . ? C2 N3 C4 111.7(3) . . ? C2 N3 C22 119.5(3) . . ? C4 N3 C22 128.8(3) . . ? C5 C4 N3 105.8(4) . . ? C5 C4 H4 127.1 . . ? N3 C4 H4 127.1 . . ? C4 C5 N1 107.6(3) . . ? C4 C5 H5 126.2 . . ? N1 C5 H5 126.2 . . ? C12 C11 C16 122.8(10) . . ? C12 C11 N1 121.9(9) . . ? C16 C11 N1 115.2(9) . . ? C11 C12 C13 119.4(9) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C14 C13 C12 121.1(9) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 119.9(9) . . ? C13 C14 H14 120 . . ? C15 C14 H14 120.1 . . ? C14 C15 C16 120.8(9) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C15 C16 C11 115.9(9) . . ? C15 C16 H16 122.1 . . ? C11 C16 H16 122.1 . . ? C16' C11' N1 127.5(14) . . ? C16' C11' C12' 119.0(17) . . ? N1 C11' C12' 113.4(12) . . ? C13' C12' C11' 119.3(15) . . ? C13' C12' H12' 120.3 . . ? C11' C12' H12' 120.3 . . ? C14' C13' C12' 118.7(15) . . ? C14' C13' H13' 120.7 . . ? C12' C13' H13' 120.7 . . ? C15' C14' C13' 121.0(13) . . ? C15' C14' H14' 119.5 . . ? C13' C14' H14' 119.5 . . ? C14' C15' C16' 119.9(13) . . ? C14' C15' H15' 120.1 . . ? C16' C15' H15' 120.1 . . ? C11' C16' C15' 121.5(17) . . ? C11' C16' H16' 119.3 . . ? C15' C16' H16' 119.2 . . ? C22 N21 C28A 116.8(3) . . ? C22 N21 Re1 114.4(2) . . ? C28A N21 Re1 128.8(2) . . ? N21 C22 N3 115.5(3) . . ? N21 C22 C23 125.3(3) . . ? N3 C22 C23 119.2(3) . . ? C24 C23 C22 117.9(3) . . ? C24 C23 H23 121 . . ? C22 C23 H23 121 . . ? C23 C24 C24A 119.6(3) . . ? C23 C24 H24 120.2 . . ? C24A C24 H24 120.2 . . ? C24 C24A C28A 119.2(3) . . ? C24 C24A C25 121.3(3) . . ? C28A C24A C25 119.5(3) . . ? C26 C25 C24A 120.5(3) . . ? C26 C25 H25 119.7 . . ? C24A C25 H25 119.7 . . ? C25 C26 C27 119.7(3) . . ? C25 C26 H26 120.2 . . ? C27 C26 H26 120.2 . . ? C28 C27 C26 120.9(4) . . ? C28 C27 H27 119.6 . . ? C26 C27 H27 119.6 . . ? C27 C28 C28A 120.9(4) . . ? C27 C28 H28 119.6 . . ? C28A C28 H28 119.6 . . ? N21 C28A C28 120.6(3) . . ? N21 C28A C24A 120.9(3) . . ? C28 C28A C24A 118.5(3) . . ? _database_code_depnum_ccdc_archive 'CCDC 934466' ####################################################################### # # 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_mxm84 #TrackingRef 'web_deposit_cif_file_0_BrianSkelton_1366243691.mxm84.cif' _audit_creation_date 2013-04-12T14:56:39-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C20 H17 Cl N5 O2 Re' _chemical_formula_moiety 'C18 H14 Cl N4 O2 Re, C2 H3 N' _chemical_formula_weight 581.04 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-p 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.1652(2) _cell_length_b 10.76130(10) _cell_length_c 15.3184(2) _cell_angle_alpha 90 _cell_angle_beta 110.527(2) _cell_angle_gamma 90 _cell_volume 2032.43(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 21844 _cell_measurement_theta_min 3.152 _cell_measurement_theta_max 36.379 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description slab _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.899 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 1 -1 0.0716 -1 -1 1 0.0655 1 0 1 0.022 -1 0 -1 0.0317 -1 1 1 0.1063 1 -1 -1 0.0987 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 6.137 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897 ; _exptl_absorpt_correction_T_min 0.404 _exptl_absorpt_correction_T_max 0.717 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 16.0009 _diffrn_orient_matrix_ub_11 -0.0521961 _diffrn_orient_matrix_ub_12 -0.0234001 _diffrn_orient_matrix_ub_13 -0.0052404 _diffrn_orient_matrix_ub_21 0.0233282 _diffrn_orient_matrix_ub_22 -0.0388366 _diffrn_orient_matrix_ub_23 0.0394227 _diffrn_orient_matrix_ub_31 -0.0065998 _diffrn_orient_matrix_ub_32 0.0478627 _diffrn_orient_matrix_ub_33 0.0294195 _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur diffractometer' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_unetI/netI 0.0239 _diffrn_reflns_number 55709 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 34 _diffrn_reflns_theta_full 34 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 8283 _reflns_number_gt 7383 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'OrtepII (Johnson, C. K. (1976)' _computing_publication_material 'WinGX Farrugia, L. J. (1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The chlorine atom and the carbonyl group trans to it are disordered over the two positions, with site occupancies refined to 0.756(6) and its complement. Geometries of the minor components were restrained to ideal values. ; _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^)+(0.0240P)^2^+1.6873P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 8283 _refine_ls_number_parameters 292 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0273 _refine_ls_wR_factor_ref 0.0588 _refine_ls_wR_factor_gt 0.057 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.107 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0 _refine_diff_density_max 2.079 _refine_diff_density_min -0.738 _refine_diff_density_rms 0.127 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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 7.231 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.416812(7) 0.287547(8) 0.621874(6) 0.01857(3) Uani 1 1 d D . . Cl1 Cl 0.61007(10) 0.35056(9) 0.66287(7) 0.0236(3) Uani 0.756(6) 1 d P A 1 C103 C 0.5702(11) 0.3232(15) 0.6574(10) 0.031(3) Uani 0.244(6) 1 d PD A 2 O103 O 0.6657(13) 0.3392(11) 0.6798(8) 0.043(2) Uani 0.244(6) 1 d P A 2 C101 C 0.2697(4) 0.2396(4) 0.5845(3) 0.0216(7) Uani 0.756(6) 1 d P A 1 O101 O 0.1777(3) 0.2061(3) 0.5596(2) 0.0303(6) Uani 0.756(6) 1 d P A 1 Cl2 Cl 0.2238(3) 0.2508(4) 0.5725(2) 0.0309(12) Uani 0.244(6) 1 d PD A 2 C102 C 0.4452(2) 0.1153(2) 0.62922(16) 0.0250(5) Uani 1 1 d . A . O102 O 0.4588(2) 0.00750(18) 0.63278(15) 0.0374(5) Uani 1 1 d . . . N1 N 0.44717(16) 0.25163(19) 0.83769(14) 0.0197(3) Uani 1 1 d . . . C11 C 0.49379(19) 0.1300(2) 0.85231(15) 0.0215(4) Uani 1 1 d . A . C12 C 0.5945(2) 0.1133(3) 0.84457(19) 0.0299(5) Uani 1 1 d . . . H12 H 0.632 0.1815 0.8306 0.036 Uiso 1 1 calc R A . C13 C 0.6397(3) -0.0046(3) 0.8576(2) 0.0399(7) Uani 1 1 d . A . H13 H 0.7086 -0.0178 0.8522 0.048 Uiso 1 1 calc R . . C14 C 0.5849(3) -0.1031(3) 0.8784(2) 0.0398(7) Uani 1 1 d . . . H14 H 0.616 -0.1839 0.8866 0.048 Uiso 1 1 calc R A . C15 C 0.4853(3) -0.0851(3) 0.8875(2) 0.0357(6) Uani 1 1 d . A . H15 H 0.4487 -0.1531 0.903 0.043 Uiso 1 1 calc R . . C16 C 0.4383(2) 0.0329(2) 0.87409(17) 0.0268(5) Uani 1 1 d . . . H16 H 0.3696 0.0462 0.8798 0.032 Uiso 1 1 calc R A . C2 C 0.42462(18) 0.3158(2) 0.75725(16) 0.0189(4) Uani 1 1 d . A . N21 N 0.38121(16) 0.48752(18) 0.63014(13) 0.0202(3) Uani 1 1 d . A . C22 C 0.37501(18) 0.5257(2) 0.71172(16) 0.0205(4) Uani 1 1 d . . . C23 C 0.3533(2) 0.6481(2) 0.72965(19) 0.0268(5) Uani 1 1 d . A . H23 H 0.3492 0.6717 0.7881 0.032 Uiso 1 1 calc R . . C24 C 0.3381(2) 0.7337(2) 0.6586(2) 0.0303(5) Uani 1 1 d . . . H24 H 0.3241 0.8183 0.6682 0.036 Uiso 1 1 calc R A . C25 C 0.3432(2) 0.6963(2) 0.5737(2) 0.0308(6) Uani 1 1 d . A . H25 H 0.3318 0.7542 0.5244 0.037 Uiso 1 1 calc R . . C26 C 0.3653(2) 0.5731(2) 0.56204(18) 0.0261(5) Uani 1 1 d . . . H26 H 0.3693 0.5476 0.504 0.031 Uiso 1 1 calc R A . N3 N 0.39546(16) 0.43181(17) 0.77856(13) 0.0198(3) Uani 1 1 d . A . C4 C 0.3988(2) 0.4376(2) 0.87065(16) 0.0228(4) Uani 1 1 d . . . H4 H 0.3815 0.5072 0.901 0.027 Uiso 1 1 calc R A . C5 C 0.4314(2) 0.3251(2) 0.90752(16) 0.0224(4) Uani 1 1 d . A . H5 H 0.4418 0.2999 0.9695 0.027 Uiso 1 1 calc R . . N31 N 0.40368(17) 0.30096(19) 0.48032(15) 0.0234(4) Uani 1 1 d . A . C31 C 0.3925(2) 0.3056(2) 0.40319(18) 0.0265(5) Uani 1 1 d . . . C32 C 0.3775(3) 0.3071(3) 0.30449(19) 0.0360(6) Uani 1 1 d . A . H32A H 0.4248 0.2447 0.2919 0.054 Uiso 1 1 calc R . . H32B H 0.3959 0.3895 0.2873 0.054 Uiso 1 1 calc R . . H32C H 0.3017 0.288 0.2678 0.054 Uiso 1 1 calc R . . N41 N 0.8758(3) 0.0792(3) 0.5888(2) 0.0537(8) Uani 1 1 d . . . C41 C 0.7980(3) 0.0415(2) 0.59523(19) 0.0340(6) Uani 1 1 d . . . C42 C 0.6989(4) 0.0021(4) 0.6085(3) 0.0726(15) Uani 1 1 d . . . H42A H 0.7171 -0.0453 0.6666 0.109 Uiso 1 1 calc R . . H42B H 0.6566 -0.0502 0.556 0.109 Uiso 1 1 calc R . . H42C H 0.6562 0.0754 0.6118 0.109 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 0.02210(4) 0.01981(4) 0.01527(4) 0.00108(3) 0.00838(3) 0.00012(3) Cl1 0.0209(8) 0.0270(4) 0.0233(4) 0.0036(3) 0.0082(4) -0.0023(4) C103 0.027(7) 0.034(7) 0.030(6) 0.004(5) 0.008(6) -0.006(5) O103 0.027(6) 0.052(6) 0.048(6) 0.016(5) 0.013(5) -0.006(5) C101 0.0268(19) 0.0193(15) 0.0202(17) 0.0008(11) 0.0101(16) -0.0013(15) O101 0.0254(14) 0.0329(15) 0.0306(14) 0.0005(10) 0.0071(11) -0.0100(12) Cl2 0.029(2) 0.0398(19) 0.0247(15) 0.0043(12) 0.0097(15) -0.0051(17) C102 0.0287(11) 0.0300(12) 0.0169(10) -0.0021(8) 0.0088(9) -0.0022(9) O102 0.0532(13) 0.0220(9) 0.0348(11) -0.0013(7) 0.0127(9) 0.0042(9) N1 0.0234(9) 0.0214(8) 0.0166(8) 0.0018(7) 0.0097(7) 0.0004(7) C11 0.0255(10) 0.0235(10) 0.0146(9) 0.0006(8) 0.0060(8) 0.0027(8) C12 0.0290(12) 0.0369(14) 0.0264(12) 0.0062(10) 0.0131(10) 0.0081(10) C13 0.0406(15) 0.0508(18) 0.0287(14) 0.0048(12) 0.0125(12) 0.0222(14) C14 0.058(2) 0.0295(13) 0.0254(13) 0.0005(10) 0.0061(13) 0.0171(13) C15 0.0502(17) 0.0231(12) 0.0260(13) 0.0011(9) 0.0037(12) -0.0002(11) C16 0.0301(12) 0.0260(11) 0.0217(11) 0.0028(9) 0.0057(9) -0.0023(9) C2 0.0198(9) 0.0208(9) 0.0169(9) 0.0011(7) 0.0075(8) -0.0008(7) N21 0.0213(8) 0.0201(8) 0.0186(9) 0.0025(7) 0.0062(7) -0.0019(7) C22 0.0207(10) 0.0194(9) 0.0207(10) 0.0010(7) 0.0063(8) -0.0022(7) C23 0.0321(12) 0.0194(10) 0.0287(12) -0.0008(9) 0.0105(10) 0.0002(9) C24 0.0333(13) 0.0190(11) 0.0357(14) 0.0018(9) 0.0083(11) 0.0016(9) C25 0.0341(13) 0.0246(12) 0.0299(13) 0.0089(9) 0.0065(11) 0.0007(10) C26 0.0298(12) 0.0248(11) 0.0209(11) 0.0053(8) 0.0056(9) -0.0012(9) N3 0.0245(9) 0.0188(8) 0.0168(8) 0.0005(6) 0.0083(7) -0.0006(7) C4 0.0273(11) 0.0240(10) 0.0190(10) -0.0039(8) 0.0105(8) -0.0037(9) C5 0.0255(11) 0.0267(10) 0.0167(10) -0.0012(8) 0.0094(8) -0.0010(8) N31 0.0256(9) 0.0261(10) 0.0195(9) -0.0010(7) 0.0091(8) -0.0032(7) C31 0.0316(12) 0.0278(12) 0.0208(11) 0.0012(8) 0.0101(9) -0.0050(9) C32 0.0417(16) 0.0480(17) 0.0187(12) 0.0000(11) 0.0112(11) -0.0091(13) N41 0.072(2) 0.0543(18) 0.0461(17) 0.0104(14) 0.0349(16) 0.0250(17) C41 0.0556(18) 0.0211(11) 0.0237(12) 0.0030(9) 0.0119(12) 0.0036(11) C42 0.087(3) 0.073(3) 0.044(2) 0.0072(19) 0.006(2) -0.047(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C102 1.886(3) . ? Re1 C101 1.888(5) . ? Re1 C103 1.937(14) . ? Re1 C2 2.062(2) . ? Re1 N31 2.119(2) . ? Re1 N21 2.215(2) . ? Re1 Cl2 2.416(4) . ? Re1 Cl1 2.4914(12) . ? C103 O103 1.19(2) . ? C101 O101 1.191(6) . ? C102 O102 1.173(3) . ? N1 C2 1.352(3) . ? N1 C5 1.403(3) . ? N1 C11 1.430(3) . ? C11 C16 1.381(3) . ? C11 C12 1.384(4) . ? C12 C13 1.386(4) . ? C13 C14 1.381(5) . ? C14 C15 1.381(5) . ? C15 C16 1.396(4) . ? C2 N3 1.378(3) . ? N21 C22 1.345(3) . ? N21 C26 1.352(3) . ? C22 C23 1.395(3) . ? C22 N3 1.396(3) . ? C23 C24 1.385(4) . ? C24 C25 1.386(4) . ? C25 C26 1.382(4) . ? N3 C4 1.397(3) . ? C4 C5 1.341(3) . ? N31 C31 1.139(3) . ? C31 C32 1.455(4) . ? N41 C41 1.138(5) . ? C41 C42 1.452(6) . ? 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 C102 Re1 C101 84.83(15) . . ? C102 Re1 C103 90.8(5) . . ? C102 Re1 C2 98.38(9) . . ? C101 Re1 C2 91.70(14) . . ? C103 Re1 C2 90.5(4) . . ? C102 Re1 N31 94.10(9) . . ? C101 Re1 N31 90.06(14) . . ? C103 Re1 N31 88.7(4) . . ? C2 Re1 N31 167.50(9) . . ? C102 Re1 N21 172.96(9) . . ? C101 Re1 N21 93.89(14) . . ? C103 Re1 N21 90.7(5) . . ? C2 Re1 N21 74.71(8) . . ? N31 Re1 N21 92.83(8) . . ? C102 Re1 Cl2 91.26(13) . . ? C103 Re1 Cl2 177.4(4) . . ? C2 Re1 Cl2 90.87(11) . . ? N31 Re1 Cl2 89.49(10) . . ? N21 Re1 Cl2 87.52(12) . . ? C102 Re1 Cl1 95.12(8) . . ? C101 Re1 Cl1 177.13(13) . . ? C2 Re1 Cl1 91.15(7) . . ? N31 Re1 Cl1 87.08(6) . . ? N21 Re1 Cl1 86.51(6) . . ? O103 C103 Re1 176.8(13) . . ? O101 C101 Re1 177.9(4) . . ? O102 C102 Re1 177.5(2) . . ? C2 N1 C5 111.3(2) . . ? C2 N1 C11 123.8(2) . . ? C5 N1 C11 124.54(19) . . ? C16 C11 C12 121.8(2) . . ? C16 C11 N1 119.7(2) . . ? C12 C11 N1 118.5(2) . . ? C11 C12 C13 118.8(3) . . ? C14 C13 C12 120.2(3) . . ? C15 C14 C13 120.5(3) . . ? C14 C15 C16 120.0(3) . . ? C11 C16 C15 118.7(3) . . ? N1 C2 N3 103.72(19) . . ? N1 C2 Re1 139.36(17) . . ? N3 C2 Re1 116.86(15) . . ? C22 N21 C26 117.7(2) . . ? C22 N21 Re1 115.66(15) . . ? C26 N21 Re1 126.62(17) . . ? N21 C22 C23 123.7(2) . . ? N21 C22 N3 113.66(19) . . ? C23 C22 N3 122.6(2) . . ? C24 C23 C22 117.2(2) . . ? C23 C24 C25 120.1(2) . . ? C26 C25 C24 118.8(2) . . ? N21 C26 C25 122.5(2) . . ? C2 N3 C22 118.68(19) . . ? C2 N3 C4 111.52(19) . . ? C22 N3 C4 129.6(2) . . ? C5 C4 N3 106.1(2) . . ? C4 C5 N1 107.4(2) . . ? C31 N31 Re1 177.1(2) . . ? N31 C31 C32 178.1(3) . . ? N41 C41 C42 175.2(4) . . ? #===END _database_code_depnum_ccdc_archive 'CCDC 934657' ####################################################################### # # 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_mxm56y #TrackingRef 'web_deposit_cif_file_3_BrianSkelton_1366179046.mxm56y.cif' _audit_creation_date 2012-07-16T10:24:58-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C24 H31 Br N3 O5.50 P Re' _chemical_formula_moiety 'C22 H26 Br N3 O5 P Re, 0.5(C4 H10 O)' _chemical_formula_weight 746.6 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-p 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.3806(5) _cell_length_b 12.9573(10) _cell_length_c 12.8904(10) _cell_angle_alpha 90 _cell_angle_beta 100.172(4) _cell_angle_gamma 90 _cell_volume 2693.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 13674 _cell_measurement_theta_min 2.7086 _cell_measurement_theta_max 34.3564 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.11 _exptl_crystal_density_diffrn 1.841 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1460 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 -1 1 0.0764 -1 2 -2 0.0685 1 1 -2 0.064 0 -1 -1 0.1 0 1 1 0.1003 -1 0 0 0.0511 1 0 0 0.0556 3 -1 1 0.0621 2 3 -3 0.0586 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 6.096 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_absorpt_correction_T_min 0.335 _exptl_absorpt_correction_T_max 0.562 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 16.0009 _diffrn_orient_matrix_ub_11 0.0050016 _diffrn_orient_matrix_ub_12 -0.0459681 _diffrn_orient_matrix_ub_13 0.0304166 _diffrn_orient_matrix_ub_21 0.0137652 _diffrn_orient_matrix_ub_22 0.0295348 _diffrn_orient_matrix_ub_23 0.0461024 _diffrn_orient_matrix_ub_31 -0.0414796 _diffrn_orient_matrix_ub_32 0.0042583 _diffrn_orient_matrix_ub_33 0.0085386 _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur diffractometer' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.057 _diffrn_reflns_av_unetI/netI 0.045 _diffrn_reflns_number 40569 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 29 _diffrn_reflns_theta_full 29 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 7154 _reflns_number_gt 6358 _reflns_threshold_expression I>2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'OrtepII (Johnson, C. K. (1976)' _computing_publication_material 'WinGX Farrugia, L. J. (1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The solvent diethyl ether molecule is disordered about a crystallographic inversion centre. Geometries were restrained to ideal values. ; _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^)+(0.0377P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 7154 _refine_ls_number_parameters 348 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0378 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0783 _refine_ls_wR_factor_gt 0.0753 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 2.381 _refine_diff_density_min -1.833 _refine_diff_density_rms 0.185 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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 7.231 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.226819(8) 0.511781(10) 0.343234(11) 0.01252(5) Uani 1 1 d . . . Br1 Br 0.09039(2) 0.60545(3) 0.24583(3) 0.01816(9) Uani 1 1 d . . . C10 C 0.3279(2) 0.4528(3) 0.4130(3) 0.0181(8) Uani 1 1 d . . . O10 O 0.39060(16) 0.4194(2) 0.4526(2) 0.0242(6) Uani 1 1 d . . . C20 C 0.2746(2) 0.5169(3) 0.2202(3) 0.0183(8) Uani 1 1 d . . . O20 O 0.3039(2) 0.5165(2) 0.1447(3) 0.0250(7) Uani 1 1 d . . . N1 N 0.29638(19) 0.7488(2) 0.3909(3) 0.0191(7) Uani 1 1 d . . . C11 C 0.3444(2) 0.7653(3) 0.3093(3) 0.0198(8) Uani 1 1 d . . . C12 C 0.4036(2) 0.6943(3) 0.2915(4) 0.0249(9) Uani 1 1 d . . . H12 H 0.413 0.6332 0.3326 0.03 Uiso 1 1 calc R . . C13 C 0.4490(3) 0.7144(3) 0.2121(4) 0.0314(10) Uani 1 1 d . . . H13 H 0.4883 0.6654 0.1967 0.038 Uiso 1 1 calc R . . C14 C 0.4373(3) 0.8045(4) 0.1559(4) 0.0360(11) Uani 1 1 d . . . H14 H 0.4701 0.8182 0.1037 0.043 Uiso 1 1 calc R . . C15 C 0.3788(3) 0.8758(4) 0.1738(4) 0.0353(11) Uani 1 1 d . . . H15 H 0.3708 0.9376 0.1336 0.042 Uiso 1 1 calc R . . C16 C 0.3316(2) 0.8561(3) 0.2512(3) 0.0247(9) Uani 1 1 d . . . H16 H 0.291 0.9043 0.2643 0.03 Uiso 1 1 calc R . . C2 C 0.2539(2) 0.6613(3) 0.4063(3) 0.0162(7) Uani 1 1 d . . . N3 N 0.21567(19) 0.6874(2) 0.4897(3) 0.0192(7) Uani 1 1 d . . . C21 C 0.1656(2) 0.6154(3) 0.5294(3) 0.0179(8) Uani 1 1 d . . . N22 N 0.16496(19) 0.5219(2) 0.4843(3) 0.0159(6) Uani 1 1 d . . . C23 C 0.1199(2) 0.4470(3) 0.5215(3) 0.0208(8) Uani 1 1 d . . . H23 H 0.1195 0.3797 0.492 0.025 Uiso 1 1 calc R . . C24 C 0.0749(2) 0.4643(4) 0.6000(3) 0.0242(9) Uani 1 1 d . . . H24 H 0.0443 0.4098 0.6243 0.029 Uiso 1 1 calc R . . C25 C 0.0745(2) 0.5617(4) 0.6433(3) 0.0260(9) Uani 1 1 d . . . H25 H 0.0424 0.5756 0.6964 0.031 Uiso 1 1 calc R . . C26 C 0.1215(2) 0.6388(3) 0.6084(3) 0.0253(9) Uani 1 1 d . . . H26 H 0.1234 0.7061 0.638 0.03 Uiso 1 1 calc R . . C4 C 0.2340(3) 0.7879(3) 0.5237(3) 0.0249(9) Uani 1 1 d . . . H4 H 0.2146 0.8225 0.5796 0.03 Uiso 1 1 calc R . . C5 C 0.2840(3) 0.8261(3) 0.4625(3) 0.0249(9) Uani 1 1 d . . . H5 H 0.3072 0.8935 0.4666 0.03 Uiso 1 1 calc R . . P1 P 0.17465(6) 0.34890(7) 0.28622(8) 0.01400(18) Uani 1 1 d . . . O11 O 0.21952(15) 0.2843(2) 0.2056(2) 0.0178(5) Uani 1 1 d . . . C111 C 0.3067(2) 0.2584(3) 0.2305(3) 0.0228(8) Uani 1 1 d . . . H11A H 0.3232 0.2439 0.3068 0.027 Uiso 1 1 calc R . . H11B H 0.3409 0.3161 0.2116 0.027 Uiso 1 1 calc R . . C112 C 0.3182(3) 0.1641(3) 0.1670(4) 0.0352(11) Uani 1 1 d . . . H11C H 0.287 0.1065 0.1899 0.053 Uiso 1 1 calc R . . H11D H 0.3773 0.1463 0.1774 0.053 Uiso 1 1 calc R . . H11E H 0.298 0.1781 0.0921 0.053 Uiso 1 1 calc R . . O12 O 0.17137(15) 0.26929(19) 0.3800(2) 0.0175(5) Uani 1 1 d . . . C121 C 0.1401(2) 0.1637(3) 0.3594(3) 0.0223(8) Uani 1 1 d . . . H12A H 0.1315 0.1492 0.2829 0.027 Uiso 1 1 calc R . . H12B H 0.0863 0.1558 0.3835 0.027 Uiso 1 1 calc R . . C122 C 0.2019(3) 0.0899(3) 0.4171(4) 0.0321(10) Uani 1 1 d . . . H12C H 0.2541 0.0955 0.3902 0.048 Uiso 1 1 calc R . . H12D H 0.1804 0.0194 0.4065 0.048 Uiso 1 1 calc R . . H12E H 0.2117 0.1063 0.4925 0.048 Uiso 1 1 calc R . . O13 O 0.08200(15) 0.3381(2) 0.2223(2) 0.0175(5) Uani 1 1 d . . . C131 C 0.0630(2) 0.3598(3) 0.1098(3) 0.0204(8) Uani 1 1 d . . . H13A H 0.0837 0.3031 0.0699 0.024 Uiso 1 1 calc R . . H13B H 0.0904 0.4247 0.0942 0.024 Uiso 1 1 calc R . . C132 C -0.0288(2) 0.3697(4) 0.0783(3) 0.0322(10) Uani 1 1 d . . . H13C H -0.0556 0.3078 0.1003 0.048 Uiso 1 1 calc R . . H13D H -0.0431 0.3772 0.0016 0.048 Uiso 1 1 calc R . . H13E H -0.0479 0.4305 0.1123 0.048 Uiso 1 1 calc R . . C101 C 0.5476(10) 0.8538(12) 0.4888(13) 0.054(4) Uani 0.5 1 d PD A -1 H10A H 0.5776 0.884 0.5542 0.081 Uiso 0.5 1 calc PR A -1 H10B H 0.5846 0.8077 0.4586 0.081 Uiso 0.5 1 calc PR A -1 H10C H 0.4999 0.8145 0.5038 0.081 Uiso 0.5 1 calc PR A -1 C102 C 0.5185(6) 0.9364(8) 0.4135(10) 0.044(3) Uani 0.5 1 d PD A -1 H10D H 0.567 0.9783 0.4034 0.053 Uiso 0.5 1 calc PR A -1 H10E H 0.4955 0.9044 0.3448 0.053 Uiso 0.5 1 calc PR A -1 O103 O 0.4580(5) 1.0031(5) 0.4420(7) 0.047(2) Uani 0.5 1 d PD A -1 C104 C 0.4857(7) 1.0725(10) 0.5247(9) 0.044(3) Uani 0.5 1 d PD A -1 H10F H 0.5401 1.101 0.5155 0.053 Uiso 0.5 1 calc PR A -1 H10G H 0.4939 1.0345 0.5924 0.053 Uiso 0.5 1 calc PR A -1 C105 C 0.4275(10) 1.1586(11) 0.5298(12) 0.040(3) Uani 0.5 1 d PD A -1 H10H H 0.4169 1.1946 0.4618 0.059 Uiso 0.5 1 calc PR A -1 H10I H 0.4517 1.2069 0.5852 0.059 Uiso 0.5 1 calc PR A -1 H10J H 0.3752 1.1315 0.5456 0.059 Uiso 0.5 1 calc PR A -1 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 0.01521(8) 0.01179(8) 0.01115(8) -0.00046(5) 0.00396(6) 0.00125(5) Br1 0.01905(18) 0.01824(18) 0.0174(2) 0.00274(14) 0.00371(14) 0.00281(13) C10 0.0243(19) 0.0137(17) 0.019(2) -0.0016(15) 0.0119(16) -0.0017(14) O10 0.0216(14) 0.0299(16) 0.0206(16) 0.0021(13) 0.0025(11) 0.0047(12) C20 0.0207(19) 0.0137(17) 0.021(2) 0.0008(15) 0.0036(16) 0.0009(13) O20 0.0394(18) 0.0195(14) 0.0210(17) 0.0021(12) 0.0187(14) 0.0007(12) N1 0.0242(16) 0.0138(15) 0.0187(18) -0.0023(13) 0.0021(13) -0.0006(12) C11 0.0226(19) 0.0173(18) 0.018(2) -0.0009(15) 0.0000(15) -0.0037(14) C12 0.021(2) 0.019(2) 0.033(3) 0.0019(17) 0.0020(17) -0.0008(15) C13 0.022(2) 0.029(2) 0.044(3) -0.003(2) 0.0061(19) -0.0017(17) C14 0.028(2) 0.038(3) 0.045(3) 0.005(2) 0.014(2) -0.0119(19) C15 0.039(3) 0.027(2) 0.039(3) 0.008(2) 0.006(2) -0.0103(19) C16 0.024(2) 0.0186(19) 0.031(2) -0.0006(17) 0.0028(17) -0.0053(15) C2 0.0184(17) 0.0180(18) 0.0110(18) 0.0015(14) -0.0004(14) 0.0032(13) N3 0.0270(17) 0.0155(16) 0.0151(17) -0.0047(13) 0.0035(13) 0.0051(12) C21 0.0205(18) 0.0206(19) 0.0114(19) -0.0012(15) -0.0002(14) 0.0060(14) N22 0.0165(15) 0.0219(16) 0.0101(16) -0.0004(12) 0.0044(12) 0.0044(12) C23 0.0222(19) 0.026(2) 0.015(2) 0.0033(16) 0.0061(15) 0.0027(15) C24 0.021(2) 0.036(2) 0.016(2) 0.0043(18) 0.0058(16) 0.0022(17) C25 0.024(2) 0.042(3) 0.013(2) -0.0011(18) 0.0069(16) 0.0100(18) C26 0.030(2) 0.031(2) 0.014(2) -0.0073(17) 0.0023(16) 0.0083(17) C4 0.035(2) 0.018(2) 0.021(2) -0.0067(16) 0.0014(17) 0.0052(16) C5 0.036(2) 0.0127(18) 0.023(2) -0.0023(16) -0.0038(17) 0.0037(15) P1 0.0167(4) 0.0138(4) 0.0118(5) 0.0006(3) 0.0033(4) 0.0002(3) O11 0.0185(13) 0.0172(13) 0.0183(15) -0.0035(11) 0.0048(11) 0.0019(10) C111 0.0202(19) 0.024(2) 0.025(2) -0.0040(17) 0.0081(16) 0.0014(15) C112 0.022(2) 0.032(2) 0.053(3) -0.017(2) 0.009(2) 0.0033(17) O12 0.0257(14) 0.0123(12) 0.0140(14) -0.0004(10) 0.0018(11) -0.0020(10) C121 0.030(2) 0.0172(19) 0.019(2) 0.0014(16) 0.0009(16) -0.0036(15) C122 0.033(2) 0.019(2) 0.045(3) 0.007(2) 0.009(2) -0.0001(17) O13 0.0171(12) 0.0220(14) 0.0131(14) 0.0019(11) 0.0019(10) 0.0006(10) C131 0.0247(19) 0.024(2) 0.0120(19) 0.0030(15) 0.0020(15) 0.0025(15) C132 0.023(2) 0.053(3) 0.017(2) 0.003(2) -0.0048(17) 0.0032(19) C101 0.065(12) 0.047(8) 0.055(11) 0.007(7) 0.026(8) 0.023(7) C102 0.024(5) 0.051(7) 0.059(9) 0.011(6) 0.013(5) -0.005(4) O103 0.044(5) 0.041(4) 0.061(6) -0.016(4) 0.020(4) -0.011(3) C104 0.035(6) 0.073(9) 0.023(6) 0.005(6) 0.004(5) 0.004(5) C105 0.049(8) 0.044(7) 0.032(7) -0.008(5) 0.023(6) 0.002(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C20 1.890(4) . ? Re1 C10 1.899(4) . ? Re1 C2 2.117(4) . ? Re1 N22 2.236(3) . ? Re1 P1 2.3457(10) . ? Re1 Br1 2.6557(4) . ? C10 O10 1.148(5) . ? C20 O20 1.159(5) . ? N1 C2 1.364(4) . ? N1 C5 1.400(5) . ? N1 C11 1.437(5) . ? C11 C12 1.385(5) . ? C11 C16 1.390(5) . ? C12 C13 1.393(6) . ? C12 H12 0.95 . ? C13 C14 1.369(6) . ? C13 H13 0.95 . ? C14 C15 1.379(6) . ? C14 H14 0.95 . ? C15 C16 1.388(6) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C2 N3 1.378(5) . ? N3 C4 1.391(5) . ? N3 C21 1.398(5) . ? C21 N22 1.343(5) . ? C21 C26 1.382(5) . ? N22 C23 1.358(5) . ? C23 C24 1.371(5) . ? C23 H23 0.95 . ? C24 C25 1.381(6) . ? C24 H24 0.95 . ? C25 C26 1.385(6) . ? C25 H25 0.95 . ? C26 H26 0.95 . ? C4 C5 1.329(6) . ? C4 H4 0.95 . ? C5 H5 0.95 . ? P1 O12 1.597(3) . ? P1 O13 1.600(3) . ? P1 O11 1.610(3) . ? O11 C111 1.447(4) . ? C111 C112 1.501(5) . ? C111 H11A 0.99 . ? C111 H11B 0.99 . ? C112 H11C 0.98 . ? C112 H11D 0.98 . ? C112 H11E 0.98 . ? O12 C121 1.469(4) . ? C121 C122 1.491(6) . ? C121 H12A 0.99 . ? C121 H12B 0.99 . ? C122 H12C 0.98 . ? C122 H12D 0.98 . ? C122 H12E 0.98 . ? O13 C131 1.455(4) . ? C131 C132 1.492(5) . ? C131 H13A 0.99 . ? C131 H13B 0.99 . ? C132 H13C 0.98 . ? C132 H13D 0.98 . ? C132 H13E 0.98 . ? C101 C102 1.466(14) . ? C101 H10A 0.98 . ? C101 H10B 0.98 . ? C101 H10C 0.98 . ? C102 O103 1.412(10) . ? C102 H10D 0.99 . ? C102 H10E 0.99 . ? O103 C104 1.407(11) . ? C104 C105 1.477(12) . ? C104 H10F 0.99 . ? C104 H10G 0.99 . ? C105 H10H 0.98 . ? C105 H10I 0.98 . ? C105 H10J 0.98 . ? 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 C20 Re1 C10 87.45(16) . . ? C20 Re1 C2 101.57(15) . . ? C10 Re1 C2 94.62(15) . . ? C20 Re1 N22 174.12(14) . . ? C10 Re1 N22 96.94(14) . . ? C2 Re1 N22 74.25(13) . . ? C20 Re1 P1 87.15(12) . . ? C10 Re1 P1 91.45(11) . . ? C2 Re1 P1 169.56(10) . . ? N22 Re1 P1 96.61(9) . . ? C20 Re1 Br1 91.50(12) . . ? C10 Re1 Br1 176.42(11) . . ? C2 Re1 Br1 82.23(10) . . ? N22 Re1 Br1 83.88(8) . . ? P1 Re1 Br1 91.92(2) . . ? O10 C10 Re1 177.3(3) . . ? O20 C20 Re1 177.8(3) . . ? C2 N1 C5 111.2(3) . . ? C2 N1 C11 126.1(3) . . ? C5 N1 C11 122.6(3) . . ? C12 C11 C16 121.1(4) . . ? C12 C11 N1 120.8(4) . . ? C16 C11 N1 118.1(3) . . ? C11 C12 C13 118.5(4) . . ? C11 C12 H12 120.7 . . ? C13 C12 H12 120.7 . . ? C14 C13 C12 120.4(4) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 121.3(4) . . ? C13 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? C14 C15 C16 119.2(4) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? C15 C16 C11 119.5(4) . . ? C15 C16 H16 120.2 . . ? C11 C16 H16 120.2 . . ? N1 C2 N3 102.9(3) . . ? N1 C2 Re1 141.5(3) . . ? N3 C2 Re1 115.5(3) . . ? C2 N3 C4 111.9(3) . . ? C2 N3 C21 120.0(3) . . ? C4 N3 C21 128.1(3) . . ? N22 C21 C26 123.5(4) . . ? N22 C21 N3 113.8(3) . . ? C26 C21 N3 122.7(4) . . ? C21 N22 C23 117.1(3) . . ? C21 N22 Re1 115.8(2) . . ? C23 N22 Re1 126.8(3) . . ? N22 C23 C24 122.7(4) . . ? N22 C23 H23 118.6 . . ? C24 C23 H23 118.6 . . ? C23 C24 C25 119.4(4) . . ? C23 C24 H24 120.3 . . ? C25 C24 H24 120.3 . . ? C24 C25 C26 119.0(4) . . ? C24 C25 H25 120.5 . . ? C26 C25 H25 120.5 . . ? C21 C26 C25 118.3(4) . . ? C21 C26 H26 120.8 . . ? C25 C26 H26 120.8 . . ? C5 C4 N3 106.4(3) . . ? C5 C4 H4 126.8 . . ? N3 C4 H4 126.8 . . ? C4 C5 N1 107.5(3) . . ? C4 C5 H5 126.2 . . ? N1 C5 H5 126.2 . . ? O12 P1 O13 100.23(14) . . ? O12 P1 O11 103.48(14) . . ? O13 P1 O11 96.99(14) . . ? O12 P1 Re1 113.77(10) . . ? O13 P1 Re1 119.99(11) . . ? O11 P1 Re1 119.19(10) . . ? C111 O11 P1 121.5(2) . . ? O11 C111 C112 106.4(3) . . ? O11 C111 H11A 110.5 . . ? C112 C111 H11A 110.5 . . ? O11 C111 H11B 110.5 . . ? C112 C111 H11B 110.5 . . ? H11A C111 H11B 108.6 . . ? C111 C112 H11C 109.5 . . ? C111 C112 H11D 109.5 . . ? H11C C112 H11D 109.5 . . ? C111 C112 H11E 109.5 . . ? H11C C112 H11E 109.5 . . ? H11D C112 H11E 109.5 . . ? C121 O12 P1 121.5(2) . . ? O12 C121 C122 108.9(3) . . ? O12 C121 H12A 109.9 . . ? C122 C121 H12A 109.9 . . ? O12 C121 H12B 109.9 . . ? C122 C121 H12B 109.9 . . ? H12A C121 H12B 108.3 . . ? C121 C122 H12C 109.5 . . ? C121 C122 H12D 109.5 . . ? H12C C122 H12D 109.5 . . ? C121 C122 H12E 109.5 . . ? H12C C122 H12E 109.5 . . ? H12D C122 H12E 109.5 . . ? C131 O13 P1 120.8(2) . . ? O13 C131 C132 108.4(3) . . ? O13 C131 H13A 110 . . ? C132 C131 H13A 110 . . ? O13 C131 H13B 110 . . ? C132 C131 H13B 110 . . ? H13A C131 H13B 108.4 . . ? C131 C132 H13C 109.5 . . ? C131 C132 H13D 109.5 . . ? H13C C132 H13D 109.5 . . ? C131 C132 H13E 109.5 . . ? H13C C132 H13E 109.5 . . ? H13D C132 H13E 109.5 . . ? O103 C102 C101 115.8(10) . . ? O103 C102 H10D 108.3 . . ? C101 C102 H10D 108.3 . . ? O103 C102 H10E 108.3 . . ? C101 C102 H10E 108.3 . . ? H10D C102 H10E 107.4 . . ? C104 O103 C102 116.1(9) . . ? O103 C104 C105 113.0(10) . . ? O103 C104 H10F 109 . . ? C105 C104 H10F 109 . . ? O103 C104 H10G 109 . . ? C105 C104 H10G 109 . . ? H10F C104 H10G 107.8 . . ? _database_code_depnum_ccdc_archive 'CCDC 934467' ####################################################################### # # 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_mxm56o #TrackingRef 'web_deposit_cif_file_4_BrianSkelton_1366179046.mxm56o.cif' _audit_creation_date 2012-07-15T16:15:02-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C22 H26 Br N3 O5 P Re' _chemical_formula_moiety 'C22 H26 Br N3 O5 P Re' _chemical_formula_weight 709.54 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-p 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4078(5) _cell_length_b 11.7586(6) _cell_length_c 12.8983(7) _cell_angle_alpha 98.323(4) _cell_angle_beta 102.735(5) _cell_angle_gamma 93.632(4) _cell_volume 1224.70(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8565 _cell_measurement_theta_min 3.5123 _cell_measurement_theta_max 33.5684 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.924 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 0 0.0179 0 -1 0 0.0248 1 0 -3 0.0536 -1 0 3 0.0517 1 0 0 0.0574 -1 -1 3 0.0551 -1 0 1 0.0571 0 0 -1 0.0444 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 6.696 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-8 ; _exptl_absorpt_correction_T_min 0.479 _exptl_absorpt_correction_T_max 0.755 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4738 _diffrn_orient_matrix_ub_11 -0.0860446 _diffrn_orient_matrix_ub_12 -0.0083919 _diffrn_orient_matrix_ub_13 -0.0209194 _diffrn_orient_matrix_ub_21 -0.0096178 _diffrn_orient_matrix_ub_22 -0.0237299 _diffrn_orient_matrix_ub_23 0.046027 _diffrn_orient_matrix_ub_31 -0.0076047 _diffrn_orient_matrix_ub_32 0.055853 _diffrn_orient_matrix_ub_33 0.026632 _diffrn_measurement_device_type 'Oxford Diffraction Gemini diffractometer' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0811 _diffrn_reflns_av_unetI/netI 0.0766 _diffrn_reflns_number 21461 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 29 _diffrn_reflns_theta_full 29 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 6495 _reflns_number_gt 5608 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'OrtepII (Johnson, C. K. (1976)' _computing_publication_material 'WinGX Farrugia, L. J. (1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0563P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 6495 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0606 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1129 _refine_ls_wR_factor_gt 0.1083 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 4.302 _refine_diff_density_min -1.685 _refine_diff_density_rms 0.26 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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 7.231 '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' 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 0.36254(2) 0.728132(17) 0.227486(17) 0.01784(8) Uani 1 1 d . . . Br1 Br 0.23355(7) 0.51097(5) 0.20503(5) 0.02079(13) Uani 1 1 d . . . C101 C 0.1644(7) 0.8012(5) 0.2299(5) 0.0226(12) Uani 1 1 d . . . O101 O 0.0516(5) 0.8497(4) 0.2319(4) 0.0306(10) Uani 1 1 d . . . C102 C 0.4031(7) 0.7428(5) 0.3805(5) 0.0242(12) Uani 1 1 d . . . O102 O 0.4209(6) 0.7479(4) 0.4726(4) 0.0335(10) Uani 1 1 d . . . N1 N 0.7291(6) 0.6317(4) 0.2388(4) 0.0186(9) Uani 1 1 d . . . C11 C 0.7838(7) 0.6250(5) 0.3502(5) 0.0208(11) Uani 1 1 d . . . C12 C 0.6813(7) 0.5659(5) 0.4016(5) 0.0215(11) Uani 1 1 d . . . H12 H 0.5757 0.5314 0.363 0.026 Uiso 1 1 calc R . . C13 C 0.7374(8) 0.5590(5) 0.5095(5) 0.0270(13) Uani 1 1 d . . . H13 H 0.6678 0.5219 0.546 0.032 Uiso 1 1 calc R . . C14 C 0.8943(7) 0.6056(5) 0.5651(5) 0.0257(12) Uani 1 1 d . . . H14 H 0.9321 0.5989 0.6388 0.031 Uiso 1 1 calc R . . C15 C 0.9958(7) 0.6619(5) 0.5129(5) 0.0265(12) Uani 1 1 d . . . H15 H 1.1031 0.6939 0.5508 0.032 Uiso 1 1 calc R . . C16 C 0.9399(7) 0.6712(5) 0.4053(5) 0.0245(12) Uani 1 1 d . . . H16 H 1.0091 0.7095 0.3694 0.029 Uiso 1 1 calc R . . C2 C 0.5769(6) 0.6591(5) 0.1909(5) 0.0180(10) Uani 1 1 d . . . N3 N 0.5811(5) 0.6466(4) 0.0837(4) 0.0177(9) Uani 1 1 d . . . N21 N 0.3177(5) 0.6980(4) 0.0500(4) 0.0183(9) Uani 1 1 d . . . C22 C 0.4448(6) 0.6660(4) 0.0073(4) 0.0179(10) Uani 1 1 d . . . C23 C 0.4374(7) 0.6506(5) -0.1022(5) 0.0230(12) Uani 1 1 d . . . H23 H 0.5295 0.6292 -0.1292 0.028 Uiso 1 1 calc R . . C24 C 0.2937(8) 0.6671(5) -0.1711(5) 0.0260(12) Uani 1 1 d . . . H24 H 0.2852 0.6574 -0.2466 0.031 Uiso 1 1 calc R . . C25 C 0.1615(7) 0.6980(5) -0.1291(5) 0.0259(12) Uani 1 1 d . . . H25 H 0.0608 0.7086 -0.1756 0.031 Uiso 1 1 calc R . . C26 C 0.1777(7) 0.7134(5) -0.0187(5) 0.0228(12) Uani 1 1 d . . . H26 H 0.087 0.7355 0.0096 0.027 Uiso 1 1 calc R . . C4 C 0.7321(7) 0.6138(5) 0.0662(5) 0.0220(11) Uani 1 1 d . . . H4 H 0.7633 0.6006 -0.0006 0.026 Uiso 1 1 calc R . . C5 C 0.8231(7) 0.6048(5) 0.1640(5) 0.0223(12) Uani 1 1 d . . . H5 H 0.9321 0.5839 0.1793 0.027 Uiso 1 1 calc R . . P1 P 0.4866(2) 0.90883(13) 0.23792(13) 0.0242(3) Uani 1 1 d . . . O11 O 0.6106(6) 0.9763(4) 0.3466(4) 0.0394(12) Uani 1 1 d . . . C111 C 0.7391(9) 0.9227(6) 0.4072(6) 0.0368(16) Uani 1 1 d . . . H11A H 0.8318 0.9187 0.3714 0.044 Uiso 1 1 calc R . . H11B H 0.6992 0.843 0.4122 0.044 Uiso 1 1 calc R . . C112 C 0.7945(10) 0.9935(6) 0.5185(6) 0.0438(18) Uani 1 1 d . . . H11C H 0.8316 1.0725 0.5127 0.066 Uiso 1 1 calc R . . H11D H 0.8849 0.959 0.5608 0.066 Uiso 1 1 calc R . . H11E H 0.703 0.9949 0.5542 0.066 Uiso 1 1 calc R . . O12 O 0.3663(6) 1.0068(4) 0.2197(4) 0.0403(12) Uani 1 1 d . . . C121 C 0.3963(10) 1.1273(6) 0.2641(7) 0.0474(19) Uani 1 1 d . . . H12A H 0.477 1.1657 0.2316 0.057 Uiso 1 1 calc R . . H12B H 0.4409 1.1374 0.3429 0.057 Uiso 1 1 calc R . . C122 C 0.2376(12) 1.1791(7) 0.2400(8) 0.059(2) Uani 1 1 d . . . H12C H 0.1919 1.1653 0.162 0.088 Uiso 1 1 calc R . . H12D H 0.2559 1.2624 0.2662 0.088 Uiso 1 1 calc R . . H12E H 0.1607 1.1436 0.2758 0.088 Uiso 1 1 calc R . . O13 O 0.5899(6) 0.9091(4) 0.1480(4) 0.0399(12) Uani 1 1 d . . . C131 C 0.6898(11) 1.0079(7) 0.1341(8) 0.051(2) Uani 1 1 d . . . H13A H 0.7672 1.0411 0.2031 0.062 Uiso 1 1 calc R . . H13B H 0.6196 1.0682 0.1102 0.062 Uiso 1 1 calc R . . C132 C 0.7817(9) 0.9681(7) 0.0511(7) 0.0443(18) Uani 1 1 d . . . H13C H 0.8499 0.908 0.0752 0.066 Uiso 1 1 calc R . . H13D H 0.8516 1.0335 0.0409 0.066 Uiso 1 1 calc R . . H13E H 0.7039 0.9367 -0.0171 0.066 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 0.01452(12) 0.02084(12) 0.01824(12) 0.00259(8) 0.00379(9) 0.00385(8) Br1 0.0167(3) 0.0237(3) 0.0227(3) 0.0039(2) 0.0058(2) 0.0029(2) C101 0.027(3) 0.021(3) 0.017(3) 0.002(2) 0.001(2) -0.005(2) O101 0.023(2) 0.032(2) 0.039(3) 0.007(2) 0.008(2) 0.0084(18) C102 0.019(3) 0.028(3) 0.024(3) 0.000(2) 0.005(2) 0.004(2) O102 0.037(3) 0.041(3) 0.023(2) 0.002(2) 0.009(2) 0.009(2) N1 0.015(2) 0.022(2) 0.021(2) 0.0081(19) 0.0054(19) 0.0039(18) C11 0.016(3) 0.023(3) 0.023(3) -0.001(2) 0.006(2) 0.006(2) C12 0.016(3) 0.022(3) 0.025(3) 0.003(2) 0.003(2) 0.000(2) C13 0.027(3) 0.033(3) 0.026(3) 0.013(3) 0.010(3) 0.011(3) C14 0.026(3) 0.032(3) 0.019(3) 0.006(2) 0.004(2) 0.008(2) C15 0.018(3) 0.034(3) 0.024(3) 0.006(3) -0.001(2) -0.001(2) C16 0.018(3) 0.031(3) 0.023(3) 0.007(2) 0.001(2) -0.001(2) C2 0.013(2) 0.019(2) 0.022(3) 0.005(2) 0.002(2) 0.0034(19) N3 0.013(2) 0.022(2) 0.018(2) 0.0013(18) 0.0027(18) 0.0029(17) N21 0.012(2) 0.020(2) 0.021(2) 0.0015(19) 0.0021(19) 0.0038(17) C22 0.015(2) 0.019(2) 0.019(3) 0.003(2) 0.004(2) 0.000(2) C23 0.023(3) 0.025(3) 0.021(3) 0.004(2) 0.005(2) 0.003(2) C24 0.028(3) 0.028(3) 0.021(3) 0.001(2) 0.005(3) 0.002(2) C25 0.018(3) 0.032(3) 0.025(3) 0.005(3) -0.001(2) 0.005(2) C26 0.019(3) 0.025(3) 0.024(3) 0.007(2) 0.002(2) 0.006(2) C4 0.018(3) 0.026(3) 0.024(3) 0.004(2) 0.007(2) 0.004(2) C5 0.014(3) 0.026(3) 0.025(3) 0.004(2) 0.002(2) 0.002(2) P1 0.0232(8) 0.0251(7) 0.0236(8) 0.0024(6) 0.0050(7) 0.0030(6) O11 0.037(3) 0.029(2) 0.044(3) 0.004(2) -0.005(2) 0.001(2) C111 0.031(4) 0.038(4) 0.036(4) 0.001(3) -0.001(3) 0.002(3) C112 0.043(4) 0.043(4) 0.039(4) 0.003(3) 0.000(4) 0.004(3) O12 0.037(3) 0.026(2) 0.051(3) 0.001(2) -0.001(2) 0.008(2) C121 0.053(5) 0.032(4) 0.052(5) -0.003(3) 0.008(4) 0.004(3) C122 0.080(7) 0.043(4) 0.063(6) 0.017(4) 0.025(5) 0.034(5) O13 0.047(3) 0.032(2) 0.043(3) -0.004(2) 0.025(3) -0.010(2) C131 0.054(5) 0.037(4) 0.071(6) 0.011(4) 0.034(5) -0.007(4) C132 0.033(4) 0.054(4) 0.053(5) 0.021(4) 0.017(4) 0.009(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C102 1.907(6) . ? Re1 C101 1.927(6) . ? Re1 C2 2.140(5) . ? Re1 N21 2.209(5) . ? Re1 P1 2.2793(16) . ? Re1 Br1 2.6602(6) . ? C101 O101 1.141(7) . ? C102 O102 1.157(7) . ? N1 C2 1.373(7) . ? N1 C5 1.391(7) . ? N1 C11 1.424(7) . ? C11 C16 1.382(8) . ? C11 C12 1.405(8) . ? C12 C13 1.383(8) . ? C12 H12 0.95 . ? C13 C14 1.390(9) . ? C13 H13 0.95 . ? C14 C15 1.389(8) . ? C14 H14 0.95 . ? C15 C16 1.387(8) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C2 N3 1.377(7) . ? N3 C22 1.392(7) . ? N3 C4 1.405(7) . ? N21 C26 1.348(7) . ? N21 C22 1.355(7) . ? C22 C23 1.385(8) . ? C23 C24 1.376(8) . ? C23 H23 0.95 . ? C24 C25 1.386(8) . ? C24 H24 0.95 . ? C25 C26 1.383(8) . ? C25 H25 0.95 . ? C26 H26 0.95 . ? C4 C5 1.345(8) . ? C4 H4 0.95 . ? C5 H5 0.95 . ? P1 O12 1.590(5) . ? P1 O13 1.595(5) . ? P1 O11 1.616(5) . ? O11 C111 1.425(8) . ? C111 C112 1.510(10) . ? C111 H11A 0.99 . ? C111 H11B 0.99 . ? C112 H11C 0.98 . ? C112 H11D 0.98 . ? C112 H11E 0.98 . ? O12 C121 1.433(8) . ? C121 C122 1.491(11) . ? C121 H12A 0.99 . ? C121 H12B 0.99 . ? C122 H12C 0.98 . ? C122 H12D 0.98 . ? C122 H12E 0.98 . ? O13 C131 1.445(8) . ? C131 C132 1.492(10) . ? C131 H13A 0.99 . ? C131 H13B 0.99 . ? C132 H13C 0.98 . ? C132 H13D 0.98 . ? C132 H13E 0.98 . ? 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 C102 Re1 C101 88.2(2) . . ? C102 Re1 C2 103.7(2) . . ? C101 Re1 C2 167.3(2) . . ? C102 Re1 N21 176.0(2) . . ? C101 Re1 N21 94.3(2) . . ? C2 Re1 N21 74.18(19) . . ? C102 Re1 P1 91.89(18) . . ? C101 Re1 P1 86.38(17) . . ? C2 Re1 P1 88.61(15) . . ? N21 Re1 P1 91.49(12) . . ? C102 Re1 Br1 90.97(18) . . ? C101 Re1 Br1 97.39(16) . . ? C2 Re1 Br1 87.14(14) . . ? N21 Re1 Br1 85.52(12) . . ? P1 Re1 Br1 175.34(4) . . ? O101 C101 Re1 176.6(5) . . ? O102 C102 Re1 176.6(5) . . ? C2 N1 C5 111.7(5) . . ? C2 N1 C11 125.1(5) . . ? C5 N1 C11 123.1(5) . . ? C16 C11 C12 120.5(6) . . ? C16 C11 N1 119.9(5) . . ? C12 C11 N1 119.5(5) . . ? C13 C12 C11 118.7(5) . . ? C13 C12 H12 120.7 . . ? C11 C12 H12 120.7 . . ? C12 C13 C14 120.8(6) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C15 C14 C13 120.0(6) . . ? C15 C14 H14 120 . . ? C13 C14 H14 120 . . ? C16 C15 C14 119.7(6) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C11 C16 C15 120.2(6) . . ? C11 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? N1 C2 N3 102.7(4) . . ? N1 C2 Re1 142.0(4) . . ? N3 C2 Re1 114.8(4) . . ? C2 N3 C22 120.1(4) . . ? C2 N3 C4 112.3(4) . . ? C22 N3 C4 127.7(5) . . ? C26 N21 C22 117.6(5) . . ? C26 N21 Re1 125.6(4) . . ? C22 N21 Re1 116.7(4) . . ? N21 C22 C23 123.1(5) . . ? N21 C22 N3 113.5(5) . . ? C23 C22 N3 123.4(5) . . ? C24 C23 C22 118.5(5) . . ? C24 C23 H23 120.7 . . ? C22 C23 H23 120.7 . . ? C23 C24 C25 119.2(6) . . ? C23 C24 H24 120.4 . . ? C25 C24 H24 120.4 . . ? C26 C25 C24 119.3(6) . . ? C26 C25 H25 120.4 . . ? C24 C25 H25 120.4 . . ? N21 C26 C25 122.2(5) . . ? N21 C26 H26 118.9 . . ? C25 C26 H26 118.9 . . ? C5 C4 N3 105.5(5) . . ? C5 C4 H4 127.2 . . ? N3 C4 H4 127.2 . . ? C4 C5 N1 107.8(5) . . ? C4 C5 H5 126.1 . . ? N1 C5 H5 126.1 . . ? O12 P1 O13 105.7(3) . . ? O12 P1 O11 97.5(3) . . ? O13 P1 O11 104.2(3) . . ? O12 P1 Re1 115.4(2) . . ? O13 P1 Re1 109.91(18) . . ? O11 P1 Re1 122.31(19) . . ? C111 O11 P1 122.4(4) . . ? O11 C111 C112 108.3(6) . . ? O11 C111 H11A 110 . . ? C112 C111 H11A 110 . . ? O11 C111 H11B 110 . . ? C112 C111 H11B 110 . . ? H11A C111 H11B 108.4 . . ? C111 C112 H11C 109.5 . . ? C111 C112 H11D 109.5 . . ? H11C C112 H11D 109.5 . . ? C111 C112 H11E 109.5 . . ? H11C C112 H11E 109.5 . . ? H11D C112 H11E 109.5 . . ? C121 O12 P1 128.2(5) . . ? O12 C121 C122 107.9(7) . . ? O12 C121 H12A 110.1 . . ? C122 C121 H12A 110.1 . . ? O12 C121 H12B 110.1 . . ? C122 C121 H12B 110.1 . . ? H12A C121 H12B 108.4 . . ? C121 C122 H12C 109.5 . . ? C121 C122 H12D 109.5 . . ? H12C C122 H12D 109.5 . . ? C121 C122 H12E 109.5 . . ? H12C C122 H12E 109.5 . . ? H12D C122 H12E 109.5 . . ? C131 O13 P1 125.0(5) . . ? O13 C131 C132 107.9(6) . . ? O13 C131 H13A 110.1 . . ? C132 C131 H13A 110.1 . . ? O13 C131 H13B 110.1 . . ? C132 C131 H13B 110.1 . . ? H13A C131 H13B 108.4 . . ? C131 C132 H13C 109.5 . . ? C131 C132 H13D 109.5 . . ? H13C C132 H13D 109.5 . . ? C131 C132 H13E 109.5 . . ? H13C C132 H13E 109.5 . . ? H13D C132 H13E 109.5 . . ? #===END _database_code_depnum_ccdc_archive 'CCDC 934468'