# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 #TrackingRef 'Compound_1a.cif' #=================================================================== # 0. AUDIT DETAILS _audit_creation_date 16-Apr-09 _audit_creation_method 'PLATON option' _audit_update_record ; 16-Apr-09 Updated by the Author E.H. Text writing by E.H. Checkcif OK 16-Apr-09 Updated by the Author E.H. 13-Jul-11 Updated by the Author E.H. ; #=================================================================== # 1. SUBMISSION DETAILS #=================================================================== # Name and address of author for X-ray correspondence _publ_contact_author_name ; Dr. Eberhardt Herdtweck ; _publ_contact_author_address ; Department Chemie, Lehrstuhl f\"ur Anorganische Chemie, Technische Universit\"at M\"unchen, Lichtenbergstrasse 4, D-85747 Garching bei M\"unchen, Germany. ; _publ_contact_author_email eberhardt.herdtweck@ch.tum.de _publ_contact_author_fax '+49(0)89 289 13473' _publ_contact_author_phone '+49(0)89 289 13143' # Publication choise FI FM FO CI CM CO _publ_requested_category ? _publ_requested_coeditor_name ? _publ_contact_letter # Include date of submission ; Date of submission: July 2011 ; #=================================================================== # 2. PROCESSING SUMMARY (JOURNAL OFFICE ONLY) #=================================================================== #=================================================================== # 3. TITLE AND AUTHOR LIST #=================================================================== _publ_section_title ; Synthesis and characterization of propylene and butylenes bridged fac-tricarbonylrhenium(I) biscarbene complexes ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address D.Canella ; Department Chemie, Lehrstuhl f\"ur Anorganische Chemie, Technische Universit\"at M\"unchen, Lichtenbergstrasse 4, D-85747 Garching bei M\"unchen, Germany. ; S.Hock ; Department Chemie, Lehrstuhl f\"ur Anorganische Chemie, Technische Universit\"at M\"unchen, Lichtenbergstrasse 4, D-85747 Garching bei M\"unchen, Germany. ; O.Hiltner ; Department Chemie, Lehrstuhl f\"ur Anorganische Chemie, Technische Universit\"at M\"unchen, Lichtenbergstrasse 4, D-85747 Garching bei M\"unchen, Germany. ; E.Herdtweck ; Department Chemie, Lehrstuhl f\"ur Anorganische Chemie, Technische Universit\"at M\"unchen, Lichtenbergstrasse 4, D-85747 Garching bei M\"unchen, Germany. ; W.A.Herrmann ; Department Chemie, Lehrstuhl f\"ur Anorganische Chemie, Technische Universit\"at M\"unchen, Lichtenbergstrasse 4, D-85747 Garching bei M\"unchen, Germany. ; F.E.Kuhn ; Department Chemie, Lehrstuhl f\"ur Anorganische Chemie, Technische Universit\"at M\"unchen, Lichtenbergstrasse 4, D-85747 Garching bei M\"unchen, Germany. ; #=================================================================== # 4. TEXT #=================================================================== _publ_section_abstract ; Nine new complexes of the type... ; # Insert blank lines between references _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). SIR92, J. Appl. Cryst. 27, 435-436. Farrugia, L. J. (1999). WinGX (Version 1.70.01 January 2005), J. Appl. Cryst. 32, 837-838. Sheldrick, G. M. (1998). SHELXS-97, University of G\"ottingen, G\"ottingen, Germany. Sheldrick, G. M. (1998). SHELXL-97, University of G\"ottingen, G\"ottingen, Germany. Spek, A. L. (2009). PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. Stoe (2004). X-AREA, Version 1.26, Stoe & Cie GmbH, Darmstadt, Germany. ; #=================================================================== data_Compound_1a _database_code_depnum_ccdc_archive 'CCDC 837181' #TrackingRef 'Compound_1a.cif' #=================================================================== #=================================================================== # 5. CHEMICAL DATA #=================================================================== _chemical_name_systematic ; ; _chemical_name_common ? _chemical_formula_moiety 'C14 H16 Br N4 O3 Re' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H16 Br N4 O3 Re' _chemical_formula_weight 554.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=================================================================== # 6. CRYSTAL DATA #=================================================================== _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 8.8504(3) _cell_length_b 15.6350(4) _cell_length_c 12.5268(4) _cell_angle_alpha 90 _cell_angle_beta 94.065(3) _cell_angle_gamma 90 _cell_volume 1729.05(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(1) _cell_measurement_reflns_used 30355 _cell_measurement_theta_min 3.77 _cell_measurement_theta_max 26.13 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.130 _exptl_crystal_density_method none _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 9.357 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.160 _exptl_absorpt_correction_T_max 0.633 _exptl_absorpt_process_details ; Delabs; source: (PLATON, Spek, 2009) ; _exptl_special_details ; Diffractometer operator E. Herdtweck exposure_time 60 s per image exposure_run_1_phi 0 exposure_omega_range 1-180 exposure_delta_omega 1.0 exposure_run_2_phi 45 exposure_omega_range 1-180 exposure_delta_omega 1.0 exposure_run_2_phi 90 exposure_omega_range 1-91 exposure_delta_omega 1.0 exposure_sum_images 451 ; _publ_section_exptl_prep ; The crystal was fixed in a capillary with perfluorinated ether and transferred to the diffractometer. ; _publ_section_exptl_refinement ; Solution and refinements with the program WinGX; Farrugia (1999). straight forward after integration (twin mode) source: (Stoe, 2004) Hydrogen atoms calculated in ideal positions (riding model). ; #=================================================================== # 7. EXPERIMENTAL DATA #=================================================================== _diffrn_ambient_temperature 293(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'NONIUS FR 591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'two-circle diffractometer' _diffrn_measurement_device_type 'IPDS 2T (Stoe)' _diffrn_measurement_method 'omega-rotation/oscillation ' _diffrn_detector 'image plate' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_decay_% 0 # number of measured reflections (redundant set) _diffrn_reflns_number 25718 _diffrn_reflns_av_R_equivalents 0.0731 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.77 _diffrn_reflns_theta_max 25.63 _reflns_number_total 3223 _reflns_number_gt 2940 # number of observed reflections (> n sig(I)) _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-AREA (Stoe, 2004)' _computing_cell_refinement 'X-AREA (Stoe, 2004)' _computing_data_reduction 'X-AREA (Stoe, 2004)' _computing_structure_solution 'SIR92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'PLATON (Spek, 2009)' #=================================================================== # 8. REFINEMENT DATA #=================================================================== _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs 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^)+(0.0397P)^2^+2.5105P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3223 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0344 _refine_ls_R_factor_gt 0.0293 _refine_ls_wR_factor_ref 0.0737 _refine_ls_wR_factor_gt 0.0712 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.63 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.761 _refine_diff_density_min -0.893 _refine_diff_density_rms 0.127 #=================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS #=================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Re1 Re Uani 0.93002(2) 0.28903(1) 0.25665(1) 1.000 0.0335(1) . . Br1 Br Uani 1.15360(6) 0.40307(4) 0.27700(4) 1.000 0.0502(2) . . O1 O Uani 1.0018(7) 0.1894(3) 0.4667(4) 1.000 0.076(2) . . O2 O Uani 1.1586(7) 0.1583(4) 0.1800(4) 1.000 0.091(2) . . O3 O Uani 0.6682(7) 0.1729(4) 0.2194(4) 1.000 0.0713(19) . . N1 N Uani 0.8952(6) 0.3036(4) -0.0012(4) 1.000 0.0504(18) . . N2 N Uani 0.8521(5) 0.4271(3) 0.0633(3) 1.000 0.0425(14) . . N3 N Uani 0.6557(5) 0.4174(3) 0.3086(3) 1.000 0.0382(14) . . N4 N Uani 0.8197(5) 0.4130(3) 0.4421(3) 1.000 0.0370(14) . . C1 C Uani 0.9760(7) 0.2307(4) 0.3927(5) 1.000 0.0476(19) . . C2 C Uani 1.0718(8) 0.2085(4) 0.2022(5) 1.000 0.056(2) . . C3 C Uani 0.7536(9) 0.2095(4) 0.2319(5) 1.000 0.048(2) . . C4 C Uani 0.8843(5) 0.3459(4) 0.0938(4) 1.000 0.0368(14) . . C5 C Uani 0.8698(7) 0.3589(6) -0.0867(4) 1.000 0.060(2) . . C6 C Uani 0.8429(7) 0.4356(5) -0.0472(5) 1.000 0.058(2) . . C7 C Uani 0.8049(7) 0.4969(4) 0.1319(5) 1.000 0.0457(17) . . C8 C Uani 0.6341(7) 0.4936(4) 0.1411(5) 1.000 0.0538(19) . . C9 C Uani 0.5843(6) 0.4155(4) 0.2009(4) 1.000 0.0439(18) . . C10 C Uani 0.6062(6) 0.4718(4) 0.3853(5) 1.000 0.0470(19) . . C11 C Uani 0.7085(7) 0.4683(4) 0.4698(4) 1.000 0.0461(17) . . C12 C Uani 0.7912(5) 0.3807(3) 0.3415(4) 1.000 0.0322(14) . . C13 C Uani 0.9228(11) 0.2132(5) -0.0189(6) 1.000 0.074(3) . . C14 C Uani 0.9472(7) 0.3909(4) 0.5193(4) 1.000 0.0473(19) . . H51 H Uiso 0.87120 0.34480 -0.15880 1.000 0.0730 calc R H61 H Uiso 0.82200 0.48540 -0.08600 1.000 0.0690 calc R H71 H Uiso 0.83230 0.55140 0.10180 1.000 0.0550 calc R H72 H Uiso 0.85670 0.49180 0.20250 1.000 0.0550 calc R H81 H Uiso 0.60280 0.54450 0.17780 1.000 0.0640 calc R H82 H Uiso 0.58360 0.49370 0.06980 1.000 0.0640 calc R H91 H Uiso 0.47500 0.41560 0.20340 1.000 0.0530 calc R H92 H Uiso 0.61340 0.36390 0.16450 1.000 0.0530 calc R H101 H Uiso 0.51860 0.50480 0.37970 1.000 0.0570 calc R H111 H Uiso 0.70480 0.49750 0.53420 1.000 0.0550 calc R H131 H Uiso 0.88300 0.18030 0.03750 1.000 0.1100 calc R H132 H Uiso 1.02980 0.20330 -0.01950 1.000 0.1100 calc R H133 H Uiso 0.87370 0.19610 -0.08640 1.000 0.1100 calc R H141 H Uiso 1.03780 0.38470 0.48220 1.000 0.0710 calc R H142 H Uiso 0.92570 0.33800 0.55420 1.000 0.0710 calc R H143 H Uiso 0.96110 0.43540 0.57170 1.000 0.0710 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 0.0351(1) 0.0342(1) 0.0308(1) -0.0029(1) 0.0001(1) 0.0037(1) Br1 0.0406(3) 0.0647(4) 0.0448(3) 0.0024(3) 0.0005(2) -0.0085(3) O1 0.118(5) 0.057(3) 0.050(3) 0.014(2) -0.009(3) 0.018(3) O2 0.090(4) 0.106(5) 0.074(3) -0.032(3) -0.005(3) 0.057(4) O3 0.069(3) 0.077(4) 0.066(3) 0.011(3) -0.008(3) 0.000(3) N1 0.047(3) 0.068(4) 0.036(2) -0.011(2) 0.001(2) 0.002(2) N2 0.039(2) 0.051(3) 0.037(2) 0.005(2) -0.0005(18) -0.004(2) N3 0.033(2) 0.041(3) 0.041(2) -0.0006(18) 0.0049(17) 0.0037(18) N4 0.037(2) 0.041(3) 0.033(2) -0.0022(18) 0.0030(17) -0.0010(18) C1 0.060(4) 0.042(3) 0.040(3) -0.005(2) -0.002(3) 0.009(3) C2 0.062(4) 0.064(4) 0.039(3) -0.016(3) -0.007(3) 0.019(3) C3 0.074(5) 0.036(3) 0.032(3) 0.001(2) -0.005(3) 0.014(3) C4 0.032(2) 0.047(3) 0.031(2) -0.005(2) -0.0012(18) -0.004(2) C5 0.052(3) 0.099(6) 0.030(3) 0.000(3) 0.001(2) -0.008(4) C6 0.050(3) 0.085(5) 0.038(3) 0.016(3) 0.002(2) -0.006(3) C7 0.050(3) 0.040(3) 0.047(3) 0.012(2) 0.002(2) -0.002(2) C8 0.050(3) 0.059(4) 0.051(3) 0.008(3) -0.006(3) 0.011(3) C9 0.028(2) 0.059(4) 0.044(3) -0.001(3) -0.002(2) 0.005(2) C10 0.041(3) 0.049(4) 0.053(3) -0.003(3) 0.018(2) 0.008(2) C11 0.050(3) 0.047(3) 0.043(3) -0.010(2) 0.015(2) 0.000(3) C12 0.035(2) 0.030(3) 0.032(2) -0.0020(19) 0.0050(18) -0.0004(19) C13 0.093(6) 0.077(6) 0.049(4) -0.032(3) -0.006(4) 0.013(4) C14 0.054(3) 0.054(4) 0.033(3) -0.007(2) -0.003(2) -0.002(3) #================================================================== # 10. MOLECULAR GEOMETRY #=================================================================== loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 Br1 2.6624(6) . . yes Re1 C1 1.950(6) . . yes Re1 C2 1.936(7) . . yes Re1 C3 2.003(7) . . yes Re1 C4 2.236(5) . . yes Re1 C12 2.209(5) . . yes O1 C1 1.140(8) . . yes O2 C2 1.146(9) . . yes O3 C3 0.952(10) . . yes N1 C4 1.371(8) . . yes N1 C5 1.382(9) . . yes N1 C13 1.454(10) . . yes N2 C4 1.350(8) . . yes N2 C6 1.387(7) . . yes N2 C7 1.468(8) . . yes N3 C9 1.449(6) . . yes N3 C10 1.378(7) . . yes N3 C12 1.366(6) . . yes N4 C11 1.373(8) . . yes N4 C12 1.364(6) . . yes N4 C14 1.474(7) . . yes C5 C6 1.325(12) . . no C7 C8 1.525(9) . . no C8 C9 1.514(9) . . no C10 C11 1.344(8) . . no C5 H51 0.9300 . . no C6 H61 0.9300 . . no C7 H71 0.9700 . . no C7 H72 0.9700 . . no C8 H81 0.9700 . . no C8 H82 0.9700 . . no C9 H91 0.9700 . . no C9 H92 0.9700 . . no C10 H101 0.9300 . . no C11 H111 0.9300 . . no C13 H131 0.9600 . . no C13 H132 0.9600 . . no C13 H133 0.9600 . . no C14 H141 0.9600 . . no C14 H142 0.9600 . . no C14 H143 0.9600 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Br1 Re1 C1 97.00(18) . . . yes Br1 Re1 C2 88.5(2) . . . yes Br1 Re1 C3 175.24(19) . . . yes Br1 Re1 C4 84.62(14) . . . yes Br1 Re1 C12 87.38(12) . . . yes C1 Re1 C2 84.5(3) . . . yes C1 Re1 C3 87.5(3) . . . yes C1 Re1 C4 175.1(2) . . . yes C1 Re1 C12 88.4(2) . . . yes C2 Re1 C3 93.4(3) . . . yes C2 Re1 C4 91.0(2) . . . yes C2 Re1 C12 171.2(2) . . . yes C3 Re1 C4 91.0(2) . . . yes C3 Re1 C12 91.3(2) . . . yes C4 Re1 C12 96.32(19) . . . yes C4 N1 C5 110.7(6) . . . yes C4 N1 C13 128.6(6) . . . yes C5 N1 C13 120.6(6) . . . yes C4 N2 C6 111.6(5) . . . yes C4 N2 C7 126.6(4) . . . yes C6 N2 C7 120.9(5) . . . yes C9 N3 C10 121.5(5) . . . yes C9 N3 C12 126.0(4) . . . yes C10 N3 C12 111.4(4) . . . yes C11 N4 C12 112.2(4) . . . yes C11 N4 C14 120.7(4) . . . yes C12 N4 C14 127.0(4) . . . yes Re1 C1 O1 173.4(6) . . . yes Re1 C2 O2 173.4(6) . . . yes Re1 C3 O3 178.5(7) . . . yes Re1 C4 N1 125.5(4) . . . yes Re1 C4 N2 130.8(4) . . . yes N1 C4 N2 103.6(5) . . . yes N1 C5 C6 107.5(5) . . . yes N2 C6 C5 106.7(6) . . . yes N2 C7 C8 110.1(5) . . . yes C7 C8 C9 112.9(5) . . . no N3 C9 C8 108.7(5) . . . yes N3 C10 C11 107.1(5) . . . yes N4 C11 C10 106.4(5) . . . yes Re1 C12 N3 129.3(3) . . . yes Re1 C12 N4 127.7(3) . . . yes N3 C12 N4 102.9(4) . . . yes N1 C5 H51 126.00 . . . no C6 C5 H51 126.00 . . . no N2 C6 H61 127.00 . . . no C5 C6 H61 127.00 . . . no N2 C7 H71 110.00 . . . no N2 C7 H72 110.00 . . . no C8 C7 H71 110.00 . . . no C8 C7 H72 110.00 . . . no H71 C7 H72 108.00 . . . no C7 C8 H81 109.00 . . . no C7 C8 H82 109.00 . . . no C9 C8 H81 109.00 . . . no C9 C8 H82 109.00 . . . no H81 C8 H82 108.00 . . . no N3 C9 H91 110.00 . . . no N3 C9 H92 110.00 . . . no C8 C9 H91 110.00 . . . no C8 C9 H92 110.00 . . . no H91 C9 H92 108.00 . . . no N3 C10 H101 126.00 . . . no C11 C10 H101 126.00 . . . no N4 C11 H111 127.00 . . . no C10 C11 H111 127.00 . . . no N1 C13 H131 110.00 . . . no N1 C13 H132 110.00 . . . no N1 C13 H133 110.00 . . . no H131 C13 H132 109.00 . . . no H131 C13 H133 109.00 . . . no H132 C13 H133 109.00 . . . no N4 C14 H141 109.00 . . . no N4 C14 H142 109.00 . . . no N4 C14 H143 110.00 . . . no H141 C14 H142 109.00 . . . no H141 C14 H143 110.00 . . . no H142 C14 H143 109.00 . . . no # End of Crystallographic Information File # Attachment 'Compound_1d.cif' # CIF-file generated for HILL 6120-173 # Compound_1d #=================================================================== data_Compound_1d _database_code_depnum_ccdc_archive 'CCDC 837182' #TrackingRef 'Compound_1d.cif' #=================================================================== #=================================================================== # 5. CHEMICAL DATA #=================================================================== _chemical_name_systematic ; ; _chemical_name_common ? _chemical_formula_moiety 'C30 H32 Br N4 O3 Re' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C30 H32 Br N4 O3 Re' _chemical_formula_weight 762.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=================================================================== # 6. CRYSTAL DATA #=================================================================== _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 8.2115(4) _cell_length_b 9.3879(4) _cell_length_c 19.7863(8) _cell_angle_alpha 95.6508(17) _cell_angle_beta 91.4818(17) _cell_angle_gamma 102.1270(18) _cell_volume 1482.32(11) _cell_formula_units_Z 2 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 9477 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 25.37 _exptl_crystal_description fragment _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.709 _exptl_crystal_density_method none _exptl_crystal_F_000 748 _exptl_absorpt_coefficient_mu 5.483 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4187 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_process_details 'SADABS, Bruker, 2008b' _exptl_special_details ; Diffractometer operator E. Herdtweck scanspeed 10 s per frame dx 35 3293 frames measured in 7 data sets phi-scan with delta_phi = 0.50 omega-scans with delta_omega = 0.50 ; _publ_section_exptl_prep ; The crystal was fixed on the top of a glass fiber with perfluorinated ether and transferred to the diffractometer. ; _publ_section_exptl_refinement ; Solution and refinements with the program WinGX; Farrugia (1999). Hydrogen atoms could not be located in the difference Fourier maps and were calculated in ideal positions (riding model). ; #=================================================================== # 7. EXPERIMENTAL DATA #=================================================================== _diffrn_ambient_temperature 173(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'rotating anode FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ' \k-geometry diffractometer ' _diffrn_measurement_device_type ' Bruker APEX-II CCD ' _diffrn_measurement_method ' phi- and omega-rotation ' _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_standards_decay_% 0 # number of measured reflections (redundant set) _diffrn_reflns_number 52637 _diffrn_reflns_av_R_equivalents 0.0562 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 25.37 _reflns_number_total 5271 _reflns_number_gt 5214 # number of observed reflections (> n sig(I)) _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX II Control Software (Bruker, 2008a)' _computing_cell_refinement 'SAINT (Bruker, 2008b)' _computing_data_reduction 'SAINT (Bruker, 2008b)' _computing_structure_solution 'SIR92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2010)' _computing_publication_material 'PLATON (Spek, 2010)' #=================================================================== # 8. REFINEMENT DATA #=================================================================== _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs 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 sigma _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0201P)^2^+4.1600P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5271 _refine_ls_number_parameters 358 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0223 _refine_ls_R_factor_gt 0.0221 _refine_ls_wR_factor_ref 0.0573 _refine_ls_wR_factor_gt 0.0571 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 25.37 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.913 _refine_diff_density_min -1.173 _refine_diff_density_rms 0.093 #=================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS #=================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Re1 Re Uani 0.75061(1) 0.94554(1) 0.24020(1) 1.000 0.0194(1) . . Br1 Br Uani 0.86893(5) 0.82133(4) 0.34024(2) 1.000 0.0325(1) . . O1 O Uani 1.0258(4) 0.8685(4) 0.14897(15) 1.000 0.0412(10) . . O2 O Uani 0.6279(4) 1.1037(4) 0.1357(2) 1.000 0.0442(11) . . O3 O Uani 1.0588(3) 1.1995(3) 0.26414(15) 1.000 0.0387(9) . . N1 N Uani 0.6277(4) 1.1466(3) 0.36455(15) 1.000 0.0255(9) . . N2 N Uani 0.4135(4) 1.0095(4) 0.31093(16) 1.000 0.0279(9) . . N3 N Uani 0.4787(4) 0.6412(3) 0.25318(16) 1.000 0.0294(9) . . N4 N Uani 0.5651(4) 0.6398(3) 0.15229(16) 1.000 0.0306(10) . . C1 C Uani 0.9142(5) 0.8859(4) 0.18063(19) 1.000 0.0275(11) . . C2 C Uani 0.6618(6) 1.0524(5) 0.1670(2) 1.000 0.0413(16) . . C3 C Uani 0.9356(5) 1.1133(4) 0.26004(18) 1.000 0.0273(11) . . C4 C Uani 0.5843(4) 1.0371(4) 0.31227(18) 1.000 0.0232(10) . . C5 C Uani 0.4885(5) 1.1841(5) 0.3937(2) 1.000 0.0353(12) . . C6 C Uani 0.3549(5) 1.0983(5) 0.3602(2) 1.000 0.0359(12) . . C7 C Uani 0.2995(4) 0.8873(5) 0.2715(2) 1.000 0.0338(11) . . C8 C Uani 0.2699(5) 0.7527(5) 0.3101(2) 1.000 0.0366(11) . . C9 C Uani 0.4248(5) 0.6910(4) 0.31922(19) 1.000 0.0313(11) . . C10 C Uani 0.5793(4) 0.7277(4) 0.21227(18) 1.000 0.0248(10) . . C11 C Uani 0.4598(6) 0.5046(5) 0.1563(2) 1.000 0.0431(16) . . C12 C Uani 0.4054(5) 0.5062(5) 0.2195(2) 1.000 0.0411(14) . . C13 C Uani 0.7918(5) 1.2241(4) 0.38994(18) 1.000 0.0251(10) . . C14 C Uani 0.8650(5) 1.3524(4) 0.36278(19) 1.000 0.0304(11) . . C15 C Uani 1.0170(5) 1.4315(4) 0.3920(2) 1.000 0.0353(11) . . C16 C Uani 1.0952(5) 1.3869(4) 0.4466(2) 1.000 0.0334(12) . . C17 C Uani 1.0147(5) 1.2610(4) 0.47406(19) 1.000 0.0317(11) . . C18 C Uani 0.8613(5) 1.1792(4) 0.44741(18) 1.000 0.0260(11) . . C19 C Uani 0.7816(6) 1.4055(5) 0.3039(2) 1.000 0.0440(14) . . C20 C Uani 1.2605(5) 1.4747(5) 0.4774(2) 1.000 0.0459(16) . . C21 C Uani 0.7697(6) 1.0524(5) 0.4827(2) 1.000 0.0362(12) . . C22 C Uani 0.6436(5) 0.6753(4) 0.08991(19) 1.000 0.0303(11) . . C23 C Uani 0.7882(5) 0.6244(4) 0.0746(2) 1.000 0.0331(11) . . C24 C Uani 0.8662(6) 0.6646(5) 0.0155(2) 1.000 0.0384(14) . . C25 C Uani 0.8031(6) 0.7504(5) -0.0275(2) 1.000 0.0412(14) . . C26 C Uani 0.6543(6) 0.7906(5) -0.0126(2) 1.000 0.0423(14) . . C27 C Uani 0.5690(5) 0.7530(4) 0.0458(2) 1.000 0.0364(12) . . C28 C Uani 0.8602(6) 0.5328(5) 0.1210(2) 1.000 0.0468(16) . . C29 C Uani 0.8948(8) 0.7988(6) -0.0893(3) 1.000 0.0640(19) . . C30 C Uani 0.4014(6) 0.7885(6) 0.0583(3) 1.000 0.0512(17) . . H51 H Uiso 0.48840 1.25720 0.43050 1.000 0.0430 calc R H61 H Uiso 0.24150 1.09830 0.36850 1.000 0.0430 calc R H71 H Uiso 0.34740 0.86440 0.22730 1.000 0.0410 calc R H72 H Uiso 0.19200 0.91530 0.26230 1.000 0.0410 calc R H81 H Uiso 0.22940 0.77850 0.35540 1.000 0.0440 calc R H82 H Uiso 0.18140 0.67590 0.28530 1.000 0.0440 calc R H91 H Uiso 0.51510 0.76750 0.34310 1.000 0.0380 calc R H92 H Uiso 0.40030 0.60810 0.34730 1.000 0.0380 calc R H111 H Uiso 0.43190 0.42610 0.12110 1.000 0.0520 calc R H121 H Uiso 0.33070 0.42930 0.23770 1.000 0.0490 calc R H151 H Uiso 1.06910 1.51890 0.37390 1.000 0.0420 calc R H171 H Uiso 1.06620 1.23020 0.51200 1.000 0.0380 calc R H191 H Uiso 0.85430 1.49390 0.29040 1.000 0.0660 calc R H192 H Uiso 0.67530 1.42810 0.31770 1.000 0.0660 calc R H193 H Uiso 0.76120 1.32890 0.26540 1.000 0.0660 calc R H201 H Uiso 1.28700 1.43610 0.51970 1.000 0.0690 calc R H202 H Uiso 1.25370 1.57760 0.48730 1.000 0.0690 calc R H203 H Uiso 1.34790 1.46730 0.44530 1.000 0.0690 calc R H211 H Uiso 0.73670 0.96540 0.44970 1.000 0.0540 calc R H212 H Uiso 0.67000 1.07760 0.50260 1.000 0.0540 calc R H213 H Uiso 0.84300 1.03200 0.51880 1.000 0.0540 calc R H241 H Uiso 0.96530 0.63240 0.00430 1.000 0.0460 calc R H261 H Uiso 0.60820 0.84570 -0.04290 1.000 0.0500 calc R H281 H Uiso 0.85780 0.57420 0.16830 1.000 0.0700 calc R H282 H Uiso 0.97570 0.53260 0.10970 1.000 0.0700 calc R H283 H Uiso 0.79400 0.43220 0.11510 1.000 0.0700 calc R H291 H Uiso 1.00280 0.86300 -0.07470 1.000 0.0960 calc R H292 H Uiso 0.82850 0.85210 -0.11520 1.000 0.0960 calc R H293 H Uiso 0.91250 0.71260 -0.11790 1.000 0.0960 calc R H301 H Uiso 0.37430 0.84890 0.02370 1.000 0.0770 calc R H302 H Uiso 0.40440 0.84240 0.10350 1.000 0.0770 calc R H303 H Uiso 0.31640 0.69740 0.05590 1.000 0.0770 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 0.0202(1) 0.0218(1) 0.0152(1) -0.0011(1) -0.0021(1) 0.0038(1) Br1 0.0331(2) 0.0375(2) 0.0288(2) 0.0040(2) -0.0014(2) 0.0119(2) O1 0.0310(15) 0.0576(19) 0.0314(16) -0.0110(14) 0.0042(13) 0.0081(13) O2 0.0355(17) 0.0382(18) 0.057(2) -0.0085(17) -0.0238(16) 0.0130(14) O3 0.0326(15) 0.0364(15) 0.0384(17) -0.0064(13) 0.0028(12) -0.0073(13) N1 0.0290(16) 0.0260(15) 0.0222(16) -0.0029(13) -0.0010(12) 0.0105(13) N2 0.0235(15) 0.0357(17) 0.0257(17) 0.0006(14) -0.0023(12) 0.0105(13) N3 0.0290(16) 0.0291(16) 0.0267(17) 0.0001(14) 0.0011(13) -0.0003(13) N4 0.0363(18) 0.0285(16) 0.0224(17) -0.0041(14) -0.0014(13) 0.0000(14) C1 0.0283(19) 0.0289(19) 0.0212(19) -0.0048(15) -0.0058(15) 0.0010(15) C2 0.044(3) 0.038(3) 0.023(2) -0.020(2) 0.017(2) -0.025(2) C3 0.032(2) 0.0287(19) 0.0215(19) -0.0013(15) 0.0018(15) 0.0091(16) C4 0.0257(17) 0.0231(17) 0.0210(18) 0.0031(15) -0.0026(14) 0.0055(14) C5 0.038(2) 0.040(2) 0.031(2) -0.0048(18) 0.0037(18) 0.0192(18) C6 0.031(2) 0.050(2) 0.032(2) 0.0006(19) 0.0040(17) 0.0224(19) C7 0.0181(17) 0.049(2) 0.032(2) -0.0044(18) -0.0029(15) 0.0063(16) C8 0.0251(19) 0.045(2) 0.035(2) -0.0009(19) 0.0036(16) -0.0010(17) C9 0.0300(19) 0.035(2) 0.026(2) 0.0038(17) 0.0048(16) -0.0002(16) C10 0.0252(18) 0.0274(18) 0.0216(18) 0.0008(15) -0.0005(14) 0.0063(14) C11 0.051(3) 0.029(2) 0.039(3) -0.0087(19) 0.000(2) -0.0089(18) C12 0.043(2) 0.029(2) 0.044(3) -0.0011(19) 0.005(2) -0.0067(18) C13 0.0304(19) 0.0241(17) 0.0207(18) -0.0055(15) -0.0017(15) 0.0098(14) C14 0.045(2) 0.0220(17) 0.024(2) -0.0030(15) -0.0011(17) 0.0099(16) C15 0.048(2) 0.0241(18) 0.030(2) -0.0030(16) 0.0041(18) 0.0019(17) C16 0.034(2) 0.034(2) 0.029(2) -0.0123(17) 0.0007(16) 0.0072(16) C17 0.037(2) 0.038(2) 0.0218(19) -0.0052(17) -0.0055(16) 0.0168(17) C18 0.037(2) 0.0245(17) 0.0183(18) -0.0015(15) 0.0006(15) 0.0128(15) C19 0.066(3) 0.029(2) 0.038(2) 0.0076(19) -0.009(2) 0.012(2) C20 0.037(2) 0.048(3) 0.046(3) -0.018(2) -0.003(2) 0.005(2) C21 0.048(2) 0.035(2) 0.027(2) 0.0053(18) 0.0028(18) 0.0109(18) C22 0.042(2) 0.0263(18) 0.0182(19) -0.0071(15) -0.0029(16) 0.0022(16) C23 0.047(2) 0.0279(19) 0.0219(19) -0.0063(16) -0.0004(17) 0.0066(17) C24 0.050(3) 0.037(2) 0.026(2) -0.0064(18) 0.0047(18) 0.0087(19) C25 0.061(3) 0.036(2) 0.021(2) -0.0035(18) 0.0018(19) 0.001(2) C26 0.062(3) 0.037(2) 0.024(2) -0.0006(18) -0.012(2) 0.005(2) C27 0.045(2) 0.032(2) 0.027(2) -0.0090(17) -0.0110(18) 0.0037(18) C28 0.064(3) 0.044(2) 0.039(3) 0.006(2) 0.010(2) 0.025(2) C29 0.092(4) 0.063(3) 0.035(3) 0.013(3) 0.015(3) 0.007(3) C30 0.047(3) 0.061(3) 0.044(3) -0.004(2) -0.014(2) 0.014(2) #================================================================== # 10. MOLECULAR GEOMETRY #=================================================================== loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 Br1 2.6557(4) . . yes Re1 C1 1.943(4) . . yes Re1 C2 2.043(4) . . yes Re1 C3 1.945(4) . . yes Re1 C4 2.234(3) . . yes Re1 C10 2.235(4) . . yes O1 C1 1.154(5) . . yes O2 C2 0.894(6) . . yes O3 C3 1.151(5) . . yes N1 C4 1.368(5) . . yes N1 C5 1.388(5) . . yes N1 C13 1.442(5) . . yes N2 C4 1.371(5) . . yes N2 C6 1.382(5) . . yes N2 C7 1.461(5) . . yes N3 C9 1.456(5) . . yes N3 C10 1.371(5) . . yes N3 C12 1.380(5) . . yes N4 C10 1.365(5) . . yes N4 C11 1.388(6) . . yes N4 C22 1.443(5) . . yes C5 C6 1.333(6) . . no C7 C8 1.520(6) . . no C8 C9 1.518(6) . . no C11 C12 1.339(6) . . no C13 C14 1.393(5) . . no C13 C18 1.399(5) . . no C14 C15 1.390(6) . . no C14 C19 1.514(6) . . no C15 C16 1.386(6) . . no C16 C17 1.395(5) . . no C16 C20 1.510(6) . . no C17 C18 1.391(6) . . no C18 C21 1.512(6) . . no C22 C23 1.400(6) . . no C22 C27 1.398(6) . . no C23 C24 1.394(6) . . no C23 C28 1.508(6) . . no C24 C25 1.389(6) . . no C25 C26 1.383(7) . . no C25 C29 1.511(7) . . no C26 C27 1.403(6) . . no C27 C30 1.504(7) . . no C5 H51 0.9500 . . no C6 H61 0.9500 . . no C7 H71 0.9900 . . no C7 H72 0.9900 . . no C8 H81 0.9900 . . no C8 H82 0.9900 . . no C9 H91 0.9900 . . no C9 H92 0.9900 . . no C11 H111 0.9500 . . no C12 H121 0.9500 . . no C15 H151 0.9500 . . no C17 H171 0.9500 . . no C19 H191 0.9800 . . no C19 H192 0.9800 . . no C19 H193 0.9800 . . no C20 H201 0.9800 . . no C20 H202 0.9800 . . no C20 H203 0.9800 . . no C21 H211 0.9800 . . no C21 H212 0.9800 . . no C21 H213 0.9800 . . no C24 H241 0.9500 . . no C26 H261 0.9500 . . no C28 H281 0.9800 . . no C28 H282 0.9800 . . no C28 H283 0.9800 . . no C29 H291 0.9800 . . no C29 H292 0.9800 . . no C29 H293 0.9800 . . no C30 H301 0.9800 . . no C30 H302 0.9800 . . no C30 H303 0.9800 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Br1 Re1 C1 89.97(11) . . . yes Br1 Re1 C2 176.60(12) . . . yes Br1 Re1 C3 88.70(11) . . . yes Br1 Re1 C4 89.87(9) . . . yes Br1 Re1 C10 85.96(9) . . . yes C1 Re1 C2 92.00(17) . . . yes C1 Re1 C3 79.83(16) . . . yes C1 Re1 C4 173.52(15) . . . yes C1 Re1 C10 89.65(14) . . . yes C2 Re1 C3 88.92(17) . . . yes C2 Re1 C4 87.87(16) . . . yes C2 Re1 C10 96.82(16) . . . yes C3 Re1 C4 93.69(15) . . . yes C3 Re1 C10 168.20(15) . . . yes C4 Re1 C10 96.80(13) . . . yes C4 N1 C5 111.7(3) . . . yes C4 N1 C13 128.8(3) . . . yes C5 N1 C13 119.4(3) . . . yes C4 N2 C6 112.2(3) . . . yes C4 N2 C7 126.5(3) . . . yes C6 N2 C7 120.7(3) . . . yes C9 N3 C10 125.3(3) . . . yes C9 N3 C12 121.5(3) . . . yes C10 N3 C12 112.1(3) . . . yes C10 N4 C11 111.8(3) . . . yes C10 N4 C22 127.2(3) . . . yes C11 N4 C22 121.0(3) . . . yes Re1 C1 O1 170.5(3) . . . yes Re1 C2 O2 176.6(5) . . . yes Re1 C3 O3 168.5(3) . . . yes Re1 C4 N1 128.3(3) . . . yes Re1 C4 N2 128.9(3) . . . yes N1 C4 N2 102.5(3) . . . yes N1 C5 C6 107.0(4) . . . yes N2 C6 C5 106.7(4) . . . yes N2 C7 C8 110.5(3) . . . yes C7 C8 C9 113.3(3) . . . no N3 C9 C8 109.9(3) . . . yes Re1 C10 N3 128.7(3) . . . yes Re1 C10 N4 128.2(3) . . . yes N3 C10 N4 102.6(3) . . . yes N4 C11 C12 106.7(4) . . . yes N3 C12 C11 106.7(4) . . . yes N1 C13 C14 119.0(3) . . . yes N1 C13 C18 118.4(3) . . . yes C14 C13 C18 122.0(4) . . . no C13 C14 C15 117.8(4) . . . no C13 C14 C19 121.4(4) . . . no C15 C14 C19 120.8(4) . . . no C14 C15 C16 122.2(4) . . . no C15 C16 C17 118.3(4) . . . no C15 C16 C20 121.1(3) . . . no C17 C16 C20 120.5(4) . . . no C16 C17 C18 121.8(4) . . . no C13 C18 C17 117.7(3) . . . no C13 C18 C21 121.9(4) . . . no C17 C18 C21 120.3(3) . . . no N4 C22 C23 118.3(3) . . . yes N4 C22 C27 119.1(4) . . . yes C23 C22 C27 122.5(4) . . . no C22 C23 C24 117.5(4) . . . no C22 C23 C28 121.5(4) . . . no C24 C23 C28 121.0(4) . . . no C23 C24 C25 121.9(4) . . . no C24 C25 C26 118.6(4) . . . no C24 C25 C29 120.8(5) . . . no C26 C25 C29 120.6(4) . . . no C25 C26 C27 122.3(4) . . . no C22 C27 C26 116.9(4) . . . no C22 C27 C30 121.8(4) . . . no C26 C27 C30 121.3(4) . . . no N1 C5 H51 127.00 . . . no C6 C5 H51 126.00 . . . no N2 C6 H61 127.00 . . . no C5 C6 H61 127.00 . . . no N2 C7 H71 110.00 . . . no N2 C7 H72 110.00 . . . no C8 C7 H71 110.00 . . . no C8 C7 H72 110.00 . . . no H71 C7 H72 108.00 . . . no C7 C8 H81 109.00 . . . no C7 C8 H82 109.00 . . . no C9 C8 H81 109.00 . . . no C9 C8 H82 109.00 . . . no H81 C8 H82 108.00 . . . no N3 C9 H91 110.00 . . . no N3 C9 H92 110.00 . . . no C8 C9 H91 110.00 . . . no C8 C9 H92 110.00 . . . no H91 C9 H92 108.00 . . . no N4 C11 H111 127.00 . . . no C12 C11 H111 127.00 . . . no N3 C12 H121 127.00 . . . no C11 C12 H121 127.00 . . . no C14 C15 H151 119.00 . . . no C16 C15 H151 119.00 . . . no C16 C17 H171 119.00 . . . no C18 C17 H171 119.00 . . . no C14 C19 H191 109.00 . . . no C14 C19 H192 110.00 . . . no C14 C19 H193 109.00 . . . no H191 C19 H192 109.00 . . . no H191 C19 H193 109.00 . . . no H192 C19 H193 109.00 . . . no C16 C20 H201 109.00 . . . no C16 C20 H202 110.00 . . . no C16 C20 H203 109.00 . . . no H201 C20 H202 109.00 . . . no H201 C20 H203 110.00 . . . no H202 C20 H203 110.00 . . . no C18 C21 H211 110.00 . . . no C18 C21 H212 109.00 . . . no C18 C21 H213 109.00 . . . no H211 C21 H212 109.00 . . . no H211 C21 H213 109.00 . . . no H212 C21 H213 109.00 . . . no C23 C24 H241 119.00 . . . no C25 C24 H241 119.00 . . . no C25 C26 H261 119.00 . . . no C27 C26 H261 119.00 . . . no C23 C28 H281 109.00 . . . no C23 C28 H282 109.00 . . . no C23 C28 H283 109.00 . . . no H281 C28 H282 109.00 . . . no H281 C28 H283 110.00 . . . no H282 C28 H283 110.00 . . . no C25 C29 H291 109.00 . . . no C25 C29 H292 109.00 . . . no C25 C29 H293 109.00 . . . no H291 C29 H292 110.00 . . . no H291 C29 H293 110.00 . . . no H292 C29 H293 110.00 . . . no C27 C30 H301 109.00 . . . no C27 C30 H302 109.00 . . . no C27 C30 H303 109.00 . . . no H301 C30 H302 109.00 . . . no H301 C30 H303 110.00 . . . no H302 C30 H303 109.00 . . . no # End of Crystallographic Information File # Attachment 'Compound_2d.cif' # CIF-file generated for HOCA 6142-173 # Compound_2d #=================================================================== data_Compound_2d _database_code_depnum_ccdc_archive 'CCDC 837183' #TrackingRef 'Compound_2d.cif' #=================================================================== #=================================================================== # 5. CHEMICAL DATA #=================================================================== _chemical_name_systematic ; ; _chemical_name_common ? _chemical_formula_moiety 'C31 H34 Br N4 O3 Re' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C31 H34 Br N4 O3 Re' _chemical_formula_weight 776.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=================================================================== # 6. CRYSTAL DATA #=================================================================== _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 2/c' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,y,1/2-z 3 -x,-y,-z 4 x,-y,1/2+z 5 1/2+x,1/2+y,z 6 1/2-x,1/2+y,1/2-z 7 1/2-x,1/2-y,-z 8 1/2+x,1/2-y,1/2+z _cell_length_a 15.1796(10) _cell_length_b 22.3292(14) _cell_length_c 18.6233(12) _cell_angle_alpha 90 _cell_angle_beta 106.295(3) _cell_angle_gamma 90 _cell_volume 6058.8(7) _cell_formula_units_Z 8 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 9753 _cell_measurement_theta_min 1.67 _cell_measurement_theta_max 25.41 _exptl_crystal_description column _exptl_crystal_colour colorless _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.703 _exptl_crystal_density_method none _exptl_crystal_F_000 3056 _exptl_absorpt_coefficient_mu 5.368 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1986 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_process_details 'SADABS, Bruker, 2008b' _exptl_special_details ; Diffractometer operator E. Herdtweck scanspeed 10 s per frame dx 35 3743 frames measured in 6 data sets phi-scan with delta_phi = 0.50 omega-scans with delta_omega = 0.50 ; _publ_section_exptl_prep ; The crystal was fixed on the top of a glass fiber with perfluorinated ether and transferred to the diffractometer. ; _publ_section_exptl_refinement ; Solution and refinements with the program WinGX; Farrugia (1999). Hydrogen atoms could not be located in the difference Fourier maps and were calculated in ideal positions (riding model). ; #=================================================================== # 7. EXPERIMENTAL DATA #=================================================================== _diffrn_ambient_temperature 173(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'rotating anode FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ' \k-geometry diffractometer ' _diffrn_measurement_device_type ' Bruker APEX-II CCD ' _diffrn_measurement_method ' phi- and omega-rotation ' _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_standards_decay_% 0 # number of measured reflections (redundant set) _diffrn_reflns_number 100450 _diffrn_reflns_av_R_equivalents 0.0719 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 25.41 _reflns_number_total 5558 _reflns_number_gt 5269 # number of observed reflections (> n sig(I)) _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX II Control Software (Bruker, 2008a)' _computing_cell_refinement 'SAINT (Bruker, 2008b)' _computing_data_reduction 'SAINT (Bruker, 2008b)' _computing_structure_solution 'SIR92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'PLATON (Spek, 2009)' #=================================================================== # 8. REFINEMENT DATA #=================================================================== _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs 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 sigma _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0086P)^2^+199.6573P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5558 _refine_ls_number_parameters 367 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.0996 _refine_ls_wR_factor_gt 0.0978 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.41 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 2.325 _refine_diff_density_min -1.533 _refine_diff_density_rms 0.181 #=================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS #=================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Re1 Re Uani 0.19861(2) 0.42992(1) 0.15238(1) 1.000 0.0159(1) . . Br1 Br Uani 0.34849(5) 0.45606(4) 0.10914(4) 1.000 0.0329(3) . . O1 O Uani 0.0150(5) 0.3965(3) 0.1727(3) 1.000 0.044(2) . . O2 O Uani 0.1049(4) 0.5047(3) 0.0124(3) 1.000 0.0382(19) . . O3 O Uani 0.1522(4) 0.3401(2) 0.0227(3) 1.000 0.0333(17) . . N1 N Uani 0.2968(4) 0.3098(3) 0.2379(3) 1.000 0.0245(19) . . N2 N Uani 0.3725(4) 0.3864(3) 0.2886(3) 1.000 0.0267(19) . . N3 N Uani 0.2092(4) 0.4971(3) 0.3114(3) 1.000 0.0210(17) . . N4 N Uani 0.2046(4) 0.5634(3) 0.2277(3) 1.000 0.0236(17) . . C1 C Uani 0.0794(6) 0.4072(4) 0.1696(4) 1.000 0.027(2) . . C2 C Uani 0.1370(5) 0.4812(3) 0.0685(4) 1.000 0.023(2) . . C3 C Uani 0.1747(5) 0.3706(3) 0.0746(4) 1.000 0.0200(19) . . C4 C Uani 0.2949(5) 0.3702(3) 0.2345(4) 1.000 0.0187(19) . . C5 C Uani 0.3731(7) 0.2894(4) 0.2934(5) 1.000 0.041(3) . . C6 C Uani 0.4204(6) 0.3373(4) 0.3243(5) 1.000 0.040(3) . . C7 C Uani 0.4028(5) 0.4480(4) 0.3108(4) 1.000 0.030(2) . . C8 C Uani 0.3948(6) 0.4629(4) 0.3904(4) 1.000 0.033(3) . . C9 C Uani 0.3137(6) 0.4360(4) 0.4121(4) 1.000 0.032(3) . . C10 C Uani 0.2190(6) 0.4412(3) 0.3543(4) 1.000 0.026(3) . . C11 C Uani 0.2075(5) 0.5023(3) 0.2373(4) 1.000 0.022(2) . . C12 C Uani 0.2092(6) 0.5518(3) 0.3450(4) 1.000 0.028(2) . . C13 C Uani 0.2063(5) 0.5938(3) 0.2931(4) 1.000 0.029(2) . . C14 C Uani 0.2347(6) 0.2687(3) 0.1887(4) 1.000 0.025(2) . . C15 C Uani 0.1528(6) 0.2526(4) 0.2037(4) 1.000 0.030(3) . . C16 C Uani 0.0955(6) 0.2125(3) 0.1550(4) 1.000 0.031(3) . . C17 C Uani 0.1193(6) 0.1888(3) 0.0932(4) 1.000 0.028(2) . . C18 C Uani 0.2031(5) 0.2042(3) 0.0818(4) 1.000 0.023(2) . . C19 C Uani 0.2620(5) 0.2445(3) 0.1287(4) 1.000 0.0229(19) . . C20 C Uani 0.1308(7) 0.2740(4) 0.2730(5) 1.000 0.041(3) . . C21 C Uani 0.0546(7) 0.1461(4) 0.0409(5) 1.000 0.042(3) . . C22 C Uani 0.3517(6) 0.2618(4) 0.1156(5) 1.000 0.032(3) . . C23 C Uani 0.1925(5) 0.5964(3) 0.1591(4) 1.000 0.024(2) . . C24 C Uani 0.1029(5) 0.6115(3) 0.1183(4) 1.000 0.026(2) . . C25 C Uani 0.0903(6) 0.6449(4) 0.0539(4) 1.000 0.033(3) . . C26 C Uani 0.1653(7) 0.6635(4) 0.0294(4) 1.000 0.035(3) . . C27 C Uani 0.2529(6) 0.6490(3) 0.0721(4) 1.000 0.033(3) . . C28 C Uani 0.2691(6) 0.6158(3) 0.1379(4) 1.000 0.030(3) . . C29 C Uani 0.0205(6) 0.5903(4) 0.1425(5) 1.000 0.039(3) . . C30 C Uani 0.1496(8) 0.6978(5) -0.0428(5) 1.000 0.056(4) . . C31 C Uani 0.3660(6) 0.6040(4) 0.1861(5) 1.000 0.039(3) . . H51 H Uiso 0.38830 0.24880 0.30650 1.000 0.0490 calc R H61 H Uiso 0.47630 0.33780 0.36340 1.000 0.0480 calc R H71 H Uiso 0.36470 0.47640 0.27430 1.000 0.0350 calc R H72 H Uiso 0.46730 0.45290 0.31010 1.000 0.0350 calc R H81 H Uiso 0.45180 0.44930 0.42740 1.000 0.0400 calc R H82 H Uiso 0.39180 0.50690 0.39490 1.000 0.0400 calc R H91 H Uiso 0.31000 0.45550 0.45890 1.000 0.0390 calc R H92 H Uiso 0.32660 0.39300 0.42330 1.000 0.0390 calc R H101 H Uiso 0.21020 0.40680 0.31940 1.000 0.0320 calc R H102 H Uiso 0.17060 0.43930 0.38040 1.000 0.0320 calc R H121 H Uiso 0.21100 0.55860 0.39570 1.000 0.0340 calc R H131 H Uiso 0.20550 0.63600 0.29970 1.000 0.0350 calc R H161 H Uiso 0.03920 0.20090 0.16380 1.000 0.0370 calc R H181 H Uiso 0.22050 0.18680 0.04120 1.000 0.0280 calc R H201 H Uiso 0.18600 0.27180 0.31560 1.000 0.0610 calc R H202 H Uiso 0.08260 0.24880 0.28270 1.000 0.0610 calc R H203 H Uiso 0.10930 0.31560 0.26590 1.000 0.0610 calc R H211 H Uiso 0.02580 0.11970 0.06990 1.000 0.0630 calc R H212 H Uiso 0.08910 0.12190 0.01410 1.000 0.0630 calc R H213 H Uiso 0.00710 0.16890 0.00480 1.000 0.0630 calc R H221 H Uiso 0.35650 0.30560 0.11490 1.000 0.0480 calc R H222 H Uiso 0.35480 0.24560 0.06740 1.000 0.0480 calc R H223 H Uiso 0.40230 0.24560 0.15580 1.000 0.0480 calc R H251 H Uiso 0.02990 0.65550 0.02580 1.000 0.0400 calc R H271 H Uiso 0.30380 0.66210 0.05600 1.000 0.0390 calc R H291 H Uiso 0.02750 0.60260 0.19430 1.000 0.0590 calc R H292 H Uiso 0.01640 0.54650 0.13890 1.000 0.0590 calc R H293 H Uiso -0.03550 0.60800 0.10980 1.000 0.0590 calc R H301 H Uiso 0.10910 0.67470 -0.08360 1.000 0.0840 calc R H302 H Uiso 0.20850 0.70450 -0.05340 1.000 0.0840 calc R H303 H Uiso 0.12110 0.73640 -0.03820 1.000 0.0840 calc R H311 H Uiso 0.40960 0.62650 0.16650 1.000 0.0570 calc R H312 H Uiso 0.37930 0.56110 0.18550 1.000 0.0570 calc R H313 H Uiso 0.37170 0.61670 0.23760 1.000 0.0570 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 0.0209(2) 0.0148(2) 0.0112(1) -0.0022(1) 0.0031(1) 0.0009(1) Br1 0.0291(4) 0.0417(5) 0.0301(4) -0.0020(4) 0.0117(3) -0.0013(3) O1 0.043(4) 0.057(4) 0.032(3) 0.005(3) 0.013(3) -0.002(3) O2 0.060(4) 0.031(3) 0.016(3) 0.006(2) -0.002(3) 0.004(3) O3 0.044(3) 0.027(3) 0.022(3) -0.005(2) -0.002(2) 0.012(2) N1 0.037(4) 0.019(3) 0.012(3) -0.003(2) -0.002(2) 0.008(3) N2 0.032(3) 0.029(4) 0.014(3) -0.007(3) -0.002(2) 0.008(3) N3 0.029(3) 0.019(3) 0.015(3) 0.001(2) 0.006(2) 0.003(2) N4 0.030(3) 0.026(3) 0.013(3) -0.001(3) 0.003(2) 0.003(3) C1 0.039(5) 0.028(4) 0.009(3) -0.007(3) -0.003(3) 0.005(4) C2 0.037(4) 0.014(3) 0.023(4) -0.005(3) 0.015(3) -0.003(3) C3 0.028(4) 0.013(3) 0.017(3) -0.004(3) 0.003(3) 0.009(3) C4 0.032(4) 0.012(3) 0.012(3) 0.006(3) 0.006(3) 0.005(3) C5 0.060(6) 0.028(4) 0.025(4) -0.006(4) -0.004(4) 0.019(4) C6 0.045(5) 0.040(5) 0.023(4) -0.009(4) -0.009(4) 0.022(4) C7 0.028(4) 0.032(4) 0.025(4) -0.007(3) 0.001(3) -0.003(3) C8 0.042(5) 0.031(4) 0.019(4) -0.007(3) -0.003(3) -0.001(4) C9 0.046(5) 0.032(4) 0.017(4) -0.001(3) 0.007(3) 0.007(4) C10 0.043(5) 0.022(4) 0.017(4) 0.002(3) 0.013(3) -0.002(3) C11 0.020(3) 0.020(4) 0.022(4) 0.011(3) 0.001(3) -0.001(3) C12 0.044(5) 0.024(4) 0.016(3) -0.010(3) 0.007(3) 0.006(3) C13 0.040(4) 0.022(4) 0.021(4) -0.013(3) 0.001(3) 0.006(3) C14 0.045(5) 0.015(3) 0.013(3) 0.001(3) 0.004(3) 0.003(3) C15 0.050(5) 0.024(4) 0.021(4) -0.001(3) 0.016(4) 0.003(3) C16 0.049(5) 0.021(4) 0.028(4) 0.002(3) 0.017(4) -0.002(3) C17 0.051(5) 0.011(3) 0.019(4) 0.000(3) 0.005(3) 0.002(3) C18 0.040(4) 0.017(4) 0.012(3) -0.003(3) 0.007(3) 0.004(3) C19 0.036(4) 0.016(3) 0.016(3) 0.003(3) 0.006(3) 0.006(3) C20 0.073(7) 0.029(4) 0.030(4) -0.007(4) 0.030(4) -0.008(4) C21 0.048(5) 0.040(5) 0.037(5) -0.015(4) 0.011(4) -0.012(4) C22 0.038(5) 0.028(4) 0.030(4) -0.006(3) 0.008(3) 0.002(3) C23 0.039(4) 0.015(3) 0.018(4) 0.000(3) 0.006(3) -0.003(3) C24 0.035(4) 0.021(4) 0.022(4) -0.001(3) 0.006(3) -0.001(3) C25 0.048(5) 0.022(4) 0.025(4) -0.004(3) 0.004(4) 0.000(4) C26 0.063(6) 0.020(4) 0.019(4) -0.006(3) 0.007(4) -0.010(4) C27 0.056(5) 0.020(4) 0.023(4) -0.002(3) 0.013(4) -0.011(4) C28 0.039(5) 0.021(4) 0.027(4) 0.000(3) 0.004(3) -0.009(3) C29 0.034(5) 0.050(5) 0.033(5) 0.005(4) 0.008(4) 0.008(4) C30 0.086(8) 0.044(6) 0.029(5) 0.013(4) 0.002(5) -0.021(5) C31 0.041(5) 0.027(4) 0.045(5) -0.002(4) 0.008(4) -0.005(4) #================================================================== # 10. MOLECULAR GEOMETRY #=================================================================== loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 Br1 2.6821(9) . . yes Re1 C1 1.990(9) . . yes Re1 C2 1.951(7) . . yes Re1 C3 1.921(7) . . yes Re1 C4 2.236(7) . . yes Re1 C11 2.239(7) . . yes O1 C1 1.024(12) . . yes O2 C2 1.148(9) . . yes O3 C3 1.153(9) . . yes N1 C4 1.350(9) . . yes N1 C5 1.395(11) . . yes N1 C14 1.444(10) . . yes N2 C4 1.367(9) . . yes N2 C6 1.379(11) . . yes N2 C7 1.472(11) . . yes N3 C10 1.467(9) . . yes N3 C11 1.378(9) . . yes N3 C12 1.372(9) . . yes N4 C11 1.375(9) . . yes N4 C13 1.388(9) . . yes N4 C23 1.441(9) . . yes C5 C6 1.326(13) . . no C7 C8 1.557(11) . . no C8 C9 1.523(13) . . no C9 C10 1.540(12) . . no C12 C13 1.339(10) . . no C14 C15 1.396(13) . . no C14 C19 1.404(11) . . no C15 C16 1.392(11) . . no C15 C20 1.499(12) . . no C16 C17 1.403(11) . . no C17 C18 1.390(12) . . no C17 C21 1.512(12) . . no C18 C19 1.391(10) . . no C19 C22 1.500(12) . . no C23 C24 1.400(11) . . no C23 C28 1.398(12) . . no C24 C25 1.379(10) . . no C24 C29 1.519(12) . . no C25 C26 1.403(14) . . no C26 C27 1.383(13) . . no C26 C30 1.507(12) . . no C27 C28 1.394(10) . . no C28 C31 1.516(13) . . no C5 H51 0.9500 . . no C6 H61 0.9500 . . no C7 H71 0.9900 . . no C7 H72 0.9900 . . no C8 H81 0.9900 . . no C8 H82 0.9900 . . no C9 H91 0.9900 . . no C9 H92 0.9900 . . no C10 H101 0.9900 . . no C10 H102 0.9900 . . no C12 H121 0.9500 . . no C13 H131 0.9500 . . no C16 H161 0.9500 . . no C18 H181 0.9500 . . no C20 H201 0.9800 . . no C20 H202 0.9800 . . no C20 H203 0.9800 . . no C21 H211 0.9800 . . no C21 H212 0.9800 . . no C21 H213 0.9800 . . no C22 H221 0.9800 . . no C22 H222 0.9800 . . no C22 H223 0.9800 . . no C25 H251 0.9500 . . no C27 H271 0.9500 . . no C29 H291 0.9800 . . no C29 H292 0.9800 . . no C29 H293 0.9800 . . no C30 H301 0.9800 . . no C30 H302 0.9800 . . no C30 H303 0.9800 . . no C31 H311 0.9800 . . no C31 H312 0.9800 . . no C31 H313 0.9800 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Br1 Re1 C1 172.0(2) . . . yes Br1 Re1 C2 83.6(2) . . . yes Br1 Re1 C3 85.4(2) . . . yes Br1 Re1 C4 83.6(2) . . . yes Br1 Re1 C11 99.6(2) . . . yes C1 Re1 C2 91.5(3) . . . yes C1 Re1 C3 87.6(3) . . . yes C1 Re1 C4 100.8(3) . . . yes C1 Re1 C11 87.0(3) . . . yes C2 Re1 C3 81.6(3) . . . yes C2 Re1 C4 166.5(3) . . . yes C2 Re1 C11 93.6(3) . . . yes C3 Re1 C4 93.1(3) . . . yes C3 Re1 C11 172.7(3) . . . yes C4 Re1 C11 92.8(3) . . . yes C4 N1 C5 111.3(6) . . . yes C4 N1 C14 127.1(6) . . . yes C5 N1 C14 121.4(7) . . . yes C4 N2 C6 112.0(7) . . . yes C4 N2 C7 126.2(6) . . . yes C6 N2 C7 121.8(6) . . . yes C10 N3 C11 126.0(6) . . . yes C10 N3 C12 121.5(6) . . . yes C11 N3 C12 112.3(6) . . . yes C11 N4 C13 112.3(6) . . . yes C11 N4 C23 127.9(6) . . . yes C13 N4 C23 119.6(6) . . . yes Re1 C1 O1 174.0(7) . . . yes Re1 C2 O2 169.2(6) . . . yes Re1 C3 O3 171.2(6) . . . yes Re1 C4 N1 129.0(5) . . . yes Re1 C4 N2 127.5(5) . . . yes N1 C4 N2 103.1(6) . . . yes N1 C5 C6 107.1(8) . . . yes N2 C6 C5 106.5(8) . . . yes N2 C7 C8 111.4(6) . . . yes C7 C8 C9 117.0(7) . . . no C8 C9 C10 116.8(6) . . . no N3 C10 C9 112.2(7) . . . yes Re1 C11 N3 128.8(5) . . . yes Re1 C11 N4 129.1(5) . . . yes N3 C11 N4 101.8(6) . . . yes N3 C12 C13 107.4(6) . . . yes N4 C13 C12 106.2(6) . . . yes N1 C14 C15 119.8(7) . . . yes N1 C14 C19 117.6(7) . . . yes C15 C14 C19 122.6(7) . . . no C14 C15 C16 117.7(7) . . . no C14 C15 C20 121.1(8) . . . no C16 C15 C20 121.1(8) . . . no C15 C16 C17 121.3(8) . . . no C16 C17 C18 119.3(7) . . . no C16 C17 C21 119.7(8) . . . no C18 C17 C21 121.0(7) . . . no C17 C18 C19 121.2(7) . . . no C14 C19 C18 117.9(7) . . . no C14 C19 C22 121.0(7) . . . no C18 C19 C22 121.2(7) . . . no N4 C23 C24 117.8(7) . . . yes N4 C23 C28 120.0(7) . . . yes C24 C23 C28 122.0(7) . . . no C23 C24 C25 118.6(7) . . . no C23 C24 C29 121.3(7) . . . no C25 C24 C29 120.1(7) . . . no C24 C25 C26 121.0(8) . . . no C25 C26 C27 118.7(7) . . . no C25 C26 C30 120.1(9) . . . no C27 C26 C30 121.2(9) . . . no C26 C27 C28 122.3(8) . . . no C23 C28 C27 117.2(8) . . . no C23 C28 C31 121.7(7) . . . no C27 C28 C31 121.0(8) . . . no N1 C5 H51 126.00 . . . no C6 C5 H51 127.00 . . . no N2 C6 H61 127.00 . . . no C5 C6 H61 127.00 . . . no N2 C7 H71 109.00 . . . no N2 C7 H72 109.00 . . . no C8 C7 H71 109.00 . . . no C8 C7 H72 109.00 . . . no H71 C7 H72 108.00 . . . no C7 C8 H81 108.00 . . . no C7 C8 H82 108.00 . . . no C9 C8 H81 108.00 . . . no C9 C8 H82 108.00 . . . no H81 C8 H82 107.00 . . . no C8 C9 H91 108.00 . . . no C8 C9 H92 108.00 . . . no C10 C9 H91 108.00 . . . no C10 C9 H92 108.00 . . . no H91 C9 H92 107.00 . . . no N3 C10 H101 109.00 . . . no N3 C10 H102 109.00 . . . no C9 C10 H101 109.00 . . . no C9 C10 H102 109.00 . . . no H101 C10 H102 108.00 . . . no N3 C12 H121 126.00 . . . no C13 C12 H121 126.00 . . . no N4 C13 H131 127.00 . . . no C12 C13 H131 127.00 . . . no C15 C16 H161 119.00 . . . no C17 C16 H161 119.00 . . . no C17 C18 H181 119.00 . . . no C19 C18 H181 119.00 . . . no C15 C20 H201 110.00 . . . no C15 C20 H202 110.00 . . . no C15 C20 H203 109.00 . . . no H201 C20 H202 110.00 . . . no H201 C20 H203 109.00 . . . no H202 C20 H203 109.00 . . . no C17 C21 H211 109.00 . . . no C17 C21 H212 109.00 . . . no C17 C21 H213 110.00 . . . no H211 C21 H212 109.00 . . . no H211 C21 H213 110.00 . . . no H212 C21 H213 109.00 . . . no C19 C22 H221 109.00 . . . no C19 C22 H222 109.00 . . . no C19 C22 H223 109.00 . . . no H221 C22 H222 109.00 . . . no H221 C22 H223 109.00 . . . no H222 C22 H223 110.00 . . . no C24 C25 H251 119.00 . . . no C26 C25 H251 120.00 . . . no C26 C27 H271 119.00 . . . no C28 C27 H271 119.00 . . . no C24 C29 H291 110.00 . . . no C24 C29 H292 109.00 . . . no C24 C29 H293 109.00 . . . no H291 C29 H292 110.00 . . . no H291 C29 H293 110.00 . . . no H292 C29 H293 109.00 . . . no C26 C30 H301 109.00 . . . no C26 C30 H302 109.00 . . . no C26 C30 H303 109.00 . . . no H301 C30 H302 109.00 . . . no H301 C30 H303 110.00 . . . no H302 C30 H303 110.00 . . . no C28 C31 H311 110.00 . . . no C28 C31 H312 109.00 . . . no C28 C31 H313 109.00 . . . no H311 C31 H312 110.00 . . . no H311 C31 H313 109.00 . . . no H312 C31 H313 109.00 . . . no # End of Crystallographic Information File