#------------------------------------------------------------------------------ #$Date: 2020-10-06 10:04:54 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257305 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/65/1556537.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1556537 loop_ _publ_author_name 'Morrison, Christine N.' 'Prosser, Kathleen E.' 'Stokes, Ryjul W.' 'Cordes, Anna' 'Metzler-Nolte, Nils' 'Cohen, Seth M.' _publ_section_title ; Expanding medicinal chemistry into 3D space: metallofragments as 3D scaffolds for fragment-based drug discovery ; _journal_issue 5 _journal_name_full 'Chemical Science' _journal_page_first 1216 _journal_page_last 1225 _journal_paper_doi 10.1039/C9SC05586J _journal_volume 11 _journal_year 2020 _chemical_formula_moiety 'C13 H9 N2 O5 Re' _chemical_formula_sum 'C13 H9 N2 O5 Re' _chemical_formula_weight 459.42 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_date 2018-06-04 _audit_creation_method ; Olex2 1.2-beta (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-10-29 deposited with the CCDC. 2019-12-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 106.800(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.1929(5) _cell_length_b 13.3161(7) _cell_length_c 11.3352(6) _cell_measurement_reflns_used 9925 _cell_measurement_temperature 100.0 _cell_measurement_theta_max 26.384 _cell_measurement_theta_min 2.314 _cell_volume 1328.36(12) _computing_cell_refinement 'SAINT v8.38A (Bruker, 2017)' _computing_data_collection 'APEX3 v2017.3-0 (Bruker, 2017)' _computing_data_reduction 'SAINT v8.38A (Bruker, 2017)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 100.0 _diffrn_detector 'Bruker APEX-II CCD' _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type 'CCD Area Detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device 'Kappa Four-Circle Diffractometer' _diffrn_measurement_device_type 'Bruker X8 APEX II' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0373 _diffrn_reflns_av_unetI/netI 0.0197 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 25383 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 26.404 _diffrn_reflns_theta_min 2.314 _diffrn_source 'sealed tube' _diffrn_source_type fine-focus _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 9.171 _exptl_absorpt_correction_T_max 0.0932 _exptl_absorpt_correction_T_min 0.0572 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0924 before and 0.0459 after correction. The Ratio of minimum to maximum transmission is 0.6137. The \l/2 correction factor is Not present.' _exptl_crystal_colour 'Light Yellow' _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 2.297 _exptl_crystal_description Block _exptl_crystal_F_000 864 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM, hexanes' _exptl_crystal_size_max 0.131 _exptl_crystal_size_mid 0.106 _exptl_crystal_size_min 0.094 _refine_diff_density_max 0.404 _refine_diff_density_min -0.587 _refine_diff_density_rms 0.089 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 191 _refine_ls_number_reflns 2729 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.068 _refine_ls_R_factor_all 0.0175 _refine_ls_R_factor_gt 0.0145 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0073P)^2^+1.6265P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0309 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2508 _reflns_number_total 2729 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc05586j2.cif _cod_data_source_block K8 _cod_depositor_comments ; The following automatic conversions were performed: data item '_diffrn_radiation_probe' value 'X-ray' was changed to 'x-ray' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. data item '_exptl_crystal_colour_modifier' value 'Light' was changed to 'light' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. data item '_exptl_crystal_colour_primary' value 'Yellow' was changed to 'yellow' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas Adding full bibliography for 1556536--1556540.cif. Adding full bibliography for 1556536--1556540.cif. ; _cod_database_code 1556537 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.479 _shelx_estimated_absorpt_t_min 0.380 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2. Shared sites {C4, N2B} {C4B, N2} 3. Uiso/Uaniso restraints and constraints Uanis(C4) = Uanis(N2B) Uanis(C4B) = Uanis(N2) 4. Others Sof(N2B)=Sof(H5B)=Sof(H8B)=Sof(C4B)=1-FVAR(1) Sof(N2)=Sof(H5A)=Sof(H8A)=Sof(C4)=FVAR(1) 5.a Aromatic/amide H refined with riding coordinates: C5(H5A), C5(H5B), C6(H6), C7(H7), C8(H8A), C8(H8B), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13) ; _shelx_res_file ; TITL CM31 in P2(1)/c cm31.res created by SHELXL-2018/3 at 13:28:45 on 04-Jun-2018 REM SHELXT solution in P2(1)/c REM R1 0.031, Rweak 0.002, Alpha 0.017, Orientation as input REM Formula found by SHELXT: C13 N O5 Re CELL 0.71073 9.1929 13.3161 11.3352 90 106.8 90 ZERR 4 0.0005 0.0007 0.0006 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O Re UNIT 52 36 8 20 4 EADP C4 N2B EADP C4B N2 EXYZ C4 N2B EXYZ C4B N2 L.S. 10 PLAN 20 SIZE 0.131 0.106 0.094 TEMP -173.15 BOND $H list 4 fmap 2 ACTA 50 OMIT 0 0 2 REM REM REM WGHT 0.007300 1.626500 FVAR 0.27862 0.36281 RE1 5 0.339005 0.521650 0.274493 11.00000 0.01222 0.01349 = 0.01244 -0.00028 0.00373 -0.00110 O1 4 0.487245 0.316591 0.354386 11.00000 0.01916 0.01652 = 0.02708 -0.00067 0.00501 0.00186 O2 4 0.167838 0.497354 0.467839 11.00000 0.02429 0.02419 = 0.01959 0.00187 0.01151 0.00199 O3 4 0.058840 0.418244 0.104516 11.00000 0.02007 0.02686 = 0.01933 -0.00043 0.00167 -0.00720 O4 4 0.543257 0.598741 0.367320 11.00000 0.01227 0.01875 = 0.01463 -0.00050 0.00454 -0.00224 O5 4 0.443242 0.550197 0.132664 11.00000 0.01410 0.02228 = 0.01398 -0.00328 0.00428 -0.00682 N1 3 0.262431 0.679628 0.242375 11.00000 0.01256 0.01721 = 0.01443 0.00018 0.00614 -0.00161 PART 1 N2 3 0.628805 0.619862 0.295813 21.00000 0.01310 0.01384 = 0.01583 -0.00059 0.00382 0.00002 PART 0 PART 2 N2B 3 0.579864 0.592894 0.174856 -21.00000 0.01442 0.01323 = 0.01551 0.00019 0.00403 -0.00067 PART 0 C1 1 0.430271 0.392234 0.321489 11.00000 0.01229 0.01972 = 0.01511 -0.00349 0.00486 -0.00383 C2 1 0.238127 0.506834 0.398639 11.00000 0.01798 0.01168 = 0.01751 -0.00095 0.00216 0.00088 C3 1 0.163862 0.457995 0.169750 11.00000 0.01744 0.01664 = 0.01676 0.00219 0.00797 0.00139 C5 1 0.668066 0.608541 0.096571 11.00000 0.01835 0.01763 = 0.01508 0.00020 0.00656 -0.00062 PART 1 AFIX 43 H5A 2 0.632962 0.587434 0.013067 21.00000 -1.20000 AFIX 43 PART 0 PART 2 H5B 2 0.632962 0.587434 0.013067 -21.00000 -1.20000 AFIX 0 PART 0 C6 1 0.805912 0.654468 0.139691 11.00000 0.01927 0.02086 = 0.02301 0.00175 0.01187 -0.00251 AFIX 43 H6 2 0.868083 0.664345 0.086740 11.00000 -1.20000 AFIX 0 C7 1 0.855352 0.686950 0.262125 11.00000 0.01360 0.01868 = 0.02407 0.00267 0.00273 -0.00247 AFIX 43 H7 2 0.949789 0.720888 0.291924 11.00000 -1.20000 AFIX 0 C8 1 0.766941 0.669636 0.339190 11.00000 0.01840 0.01568 = 0.01635 -0.00251 0.00266 -0.00118 PART 1 AFIX 43 H8A 2 0.800295 0.691741 0.422369 21.00000 -1.20000 AFIX 43 PART 0 PART 2 H8B 2 0.800295 0.691741 0.422369 -21.00000 -1.20000 AFIX 0 PART 0 C9 1 0.300943 0.744816 0.336950 11.00000 0.01723 0.01932 = 0.01684 -0.00005 0.00545 -0.00144 AFIX 43 H9 2 0.360558 0.721336 0.415119 11.00000 -1.20000 AFIX 0 C10 1 0.257412 0.844568 0.325184 11.00000 0.02061 0.01807 = 0.02040 -0.00368 0.00968 -0.00228 AFIX 43 H10 2 0.286381 0.888586 0.393977 11.00000 -1.20000 AFIX 0 C11 1 0.170606 0.879258 0.211034 11.00000 0.01691 0.01656 = 0.02761 0.00430 0.00978 -0.00080 AFIX 43 H11 2 0.138503 0.947317 0.200300 11.00000 -1.20000 AFIX 0 C12 1 0.131854 0.812702 0.113311 11.00000 0.01103 0.02242 = 0.01819 0.00518 -0.00067 -0.00181 AFIX 43 H12 2 0.072927 0.834601 0.034159 11.00000 -1.20000 AFIX 0 C13 1 0.179383 0.714485 0.131712 11.00000 0.01306 0.02090 = 0.01507 -0.00044 0.00312 -0.00574 AFIX 43 H13 2 0.152663 0.669471 0.063826 11.00000 -1.20000 AFIX 0 PART 1 C4 1 0.579864 0.592894 0.174856 21.00000 0.01442 0.01323 = 0.01551 0.00019 0.00403 -0.00067 PART 0 PART 2 C4B 1 0.628805 0.619862 0.295813 -21.00000 0.01310 0.01384 = 0.01583 -0.00059 0.00382 0.00002 HKLF 4 REM CM31 in P2(1)/c REM wR2 = 0.0309, GooF = S = 1.068, Restrained GooF = 1.068 for all data REM R1 = 0.0145 for 2508 Fo > 4sig(Fo) and 0.0175 for all 2729 data REM 191 parameters refined using 0 restraints END WGHT 0.0073 1.6265 REM Highest difference peak 0.404, deepest hole -0.587, 1-sigma level 0.089 Q1 1 0.1828 0.8482 0.2689 11.00000 0.05 0.40 Q2 1 0.3640 0.4788 0.2319 11.00000 0.05 0.39 Q3 1 0.6216 0.6172 0.1389 11.00000 0.05 0.36 Q4 1 0.6155 0.6005 0.2427 11.00000 0.05 0.35 Q5 1 0.3780 0.6932 0.4319 11.00000 0.05 0.34 Q6 1 0.6859 0.5213 0.3584 11.00000 0.05 0.34 Q7 1 0.7252 0.6526 0.1150 11.00000 0.05 0.31 Q8 1 0.5785 0.6153 0.3300 11.00000 0.05 0.31 Q9 1 0.2655 0.7736 0.0603 11.00000 0.05 0.29 Q10 1 0.6463 0.3147 0.4518 11.00000 0.05 0.28 Q11 1 0.2563 0.5204 0.1859 11.00000 0.05 0.28 Q12 1 0.5599 0.4768 0.3017 11.00000 0.05 0.28 Q13 1 1.0019 0.6314 0.0800 11.00000 0.05 0.28 Q14 1 0.9070 0.8362 0.2394 11.00000 0.05 0.27 Q15 1 0.6824 0.6658 0.3099 11.00000 0.05 0.27 Q16 1 0.0920 0.8852 0.2034 11.00000 0.05 0.27 Q17 1 0.3080 0.9648 0.3831 11.00000 0.05 0.27 Q18 1 0.4728 0.2330 0.3454 11.00000 0.05 0.26 Q19 1 0.1810 0.8590 0.1648 11.00000 0.05 0.26 Q20 1 0.4305 0.5883 0.0797 11.00000 0.05 0.26 ; _shelx_res_checksum 29628 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Re1 Re 0.33901(2) 0.52165(2) 0.27449(2) 0.01268(4) Uani 1 1 d . . . . O1 O 0.4872(2) 0.31659(14) 0.35439(19) 0.0213(5) Uani 1 1 d . . . . O2 O 0.1678(2) 0.49735(15) 0.46784(18) 0.0216(5) Uani 1 1 d . . . . O3 O 0.0588(2) 0.41824(15) 0.10452(18) 0.0229(5) Uani 1 1 d . . . . O4 O 0.5433(2) 0.59874(14) 0.36732(16) 0.0151(4) Uani 1 1 d . . . . O5 O 0.4432(2) 0.55020(14) 0.13266(17) 0.0167(4) Uani 1 1 d . . . . N1 N 0.2624(3) 0.67963(17) 0.2424(2) 0.0143(5) Uani 1 1 d . . . . N2 N 0.6288(3) 0.61986(18) 0.2958(2) 0.0143(6) Uani 0.36(2) 1 d . P A 1 N2B N 0.5799(3) 0.59289(17) 0.1749(2) 0.0145(6) Uani 0.64(2) 1 d . P A 2 C1 C 0.4303(3) 0.3922(2) 0.3215(2) 0.0155(6) Uani 1 1 d . . . . C2 C 0.2381(3) 0.50683(19) 0.3986(3) 0.0163(6) Uani 1 1 d . . . . C3 C 0.1639(3) 0.4580(2) 0.1697(3) 0.0163(6) Uani 1 1 d . . . . C5 C 0.6681(3) 0.6085(2) 0.0966(3) 0.0167(6) Uani 1 1 d . . . . H5A H 0.632962 0.587434 0.013067 0.020 Uiso 0.36(2) 1 calc R P A 1 H5B H 0.632962 0.587434 0.013067 0.020 Uiso 0.64(2) 1 calc R P A 2 C6 C 0.8059(3) 0.6545(2) 0.1397(3) 0.0198(6) Uani 1 1 d . . . . H6 H 0.868083 0.664345 0.086740 0.024 Uiso 1 1 calc R . . . C7 C 0.8554(3) 0.6870(2) 0.2621(3) 0.0194(6) Uani 1 1 d . . . . H7 H 0.949789 0.720888 0.291924 0.023 Uiso 1 1 calc R . . . C8 C 0.7669(3) 0.6696(2) 0.3392(3) 0.0173(6) Uani 1 1 d . . . . H8A H 0.800295 0.691741 0.422369 0.021 Uiso 0.36(2) 1 calc R P A 1 H8B H 0.800295 0.691741 0.422369 0.021 Uiso 0.64(2) 1 calc R P A 2 C9 C 0.3009(3) 0.7448(2) 0.3370(3) 0.0177(6) Uani 1 1 d . . . . H9 H 0.360558 0.721336 0.415119 0.021 Uiso 1 1 calc R . . . C10 C 0.2574(3) 0.8446(2) 0.3252(3) 0.0189(6) Uani 1 1 d . . . . H10 H 0.286381 0.888586 0.393977 0.023 Uiso 1 1 calc R . . . C11 C 0.1706(3) 0.8793(2) 0.2110(3) 0.0197(6) Uani 1 1 d . . . . H11 H 0.138503 0.947317 0.200300 0.024 Uiso 1 1 calc R . . . C12 C 0.1319(3) 0.8127(2) 0.1133(3) 0.0182(6) Uani 1 1 d . . . . H12 H 0.072927 0.834601 0.034159 0.022 Uiso 1 1 calc R . . . C13 C 0.1794(3) 0.7145(2) 0.1317(3) 0.0165(6) Uani 1 1 d . . . . H13 H 0.152663 0.669471 0.063826 0.020 Uiso 1 1 calc R . . . C4 C 0.5799(3) 0.59289(17) 0.1749(2) 0.0145(6) Uani 0.36(2) 1 d . P A 1 C4B C 0.6288(3) 0.61986(18) 0.2958(2) 0.0143(6) Uani 0.64(2) 1 d . P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Re1 0.01222(6) 0.01349(6) 0.01244(6) -0.00028(4) 0.00373(4) -0.00110(5) O1 0.0192(11) 0.0165(10) 0.0271(11) -0.0007(9) 0.0050(9) 0.0019(9) O2 0.0243(12) 0.0242(11) 0.0196(11) 0.0019(8) 0.0115(9) 0.0020(9) O3 0.0201(11) 0.0269(12) 0.0193(11) -0.0004(9) 0.0017(9) -0.0072(9) O4 0.0123(10) 0.0188(10) 0.0146(10) -0.0005(8) 0.0045(8) -0.0022(8) O5 0.0141(10) 0.0223(10) 0.0140(10) -0.0033(8) 0.0043(8) -0.0068(8) N1 0.0126(12) 0.0172(12) 0.0144(11) 0.0002(9) 0.0061(10) -0.0016(10) N2 0.0131(14) 0.0138(13) 0.0158(13) -0.0006(10) 0.0038(11) 0.0000(10) N2B 0.0144(13) 0.0132(12) 0.0155(13) 0.0002(10) 0.0040(10) -0.0007(10) C1 0.0123(14) 0.0197(15) 0.0151(14) -0.0035(12) 0.0049(11) -0.0038(12) C2 0.0180(15) 0.0117(13) 0.0175(14) -0.0009(11) 0.0022(12) 0.0009(11) C3 0.0174(15) 0.0166(14) 0.0168(14) 0.0022(11) 0.0080(12) 0.0014(12) C5 0.0183(15) 0.0176(14) 0.0151(14) 0.0002(11) 0.0066(12) -0.0006(12) C6 0.0193(16) 0.0209(15) 0.0230(15) 0.0017(12) 0.0119(13) -0.0025(13) C7 0.0136(15) 0.0187(14) 0.0241(16) 0.0027(12) 0.0027(12) -0.0025(12) C8 0.0184(16) 0.0157(14) 0.0163(14) -0.0025(11) 0.0027(12) -0.0012(12) C9 0.0172(15) 0.0193(14) 0.0168(14) -0.0001(11) 0.0055(12) -0.0014(12) C10 0.0206(16) 0.0181(14) 0.0204(15) -0.0037(12) 0.0097(13) -0.0023(12) C11 0.0169(15) 0.0166(14) 0.0276(16) 0.0043(12) 0.0098(13) -0.0008(12) C12 0.0110(14) 0.0224(15) 0.0182(15) 0.0052(12) -0.0007(12) -0.0018(12) C13 0.0131(14) 0.0209(15) 0.0151(14) -0.0004(11) 0.0031(11) -0.0057(12) C4 0.0144(13) 0.0132(12) 0.0155(13) 0.0002(10) 0.0040(10) -0.0007(10) C4B 0.0131(14) 0.0138(13) 0.0158(13) -0.0006(10) 0.0038(11) 0.0000(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O4 Re1 N1 79.43(8) O5 Re1 O4 76.26(7) O5 Re1 N1 84.11(8) C1 Re1 O4 92.48(9) C1 Re1 O5 96.52(10) C1 Re1 N1 171.52(10) C2 Re1 O4 103.44(10) C2 Re1 O5 175.24(9) C2 Re1 N1 91.16(10) C2 Re1 C1 88.23(11) C3 Re1 O4 171.47(9) C3 Re1 O5 95.32(10) C3 Re1 N1 98.58(10) C3 Re1 C1 89.79(11) C3 Re1 C2 84.84(12) N2 O4 Re1 113.44(15) C4B O4 Re1 113.44(15) N2B O5 Re1 112.80(15) C4 O5 Re1 112.80(15) C9 N1 Re1 118.95(18) C9 N1 C13 117.9(2) C13 N1 Re1 123.19(18) O4 N2 C8 122.2(2) O4 N2 C4 118.9(2) C4 N2 C8 118.9(2) O5 N2B C5 120.0(2) O5 N2B C4B 118.4(2) C4B N2B C5 121.5(2) O1 C1 Re1 177.1(2) O2 C2 Re1 175.4(2) O3 C3 Re1 178.6(3) N2B C5 H5B 120.2 C6 C5 N2B 119.7(3) C6 C5 H5A 120.2 C6 C5 H5B 120.2 C6 C5 C4 119.7(3) C4 C5 H5A 120.2 C5 C6 H6 120.1 C5 C6 C7 119.7(3) C7 C6 H6 120.1 C6 C7 H7 120.1 C8 C7 C6 119.8(3) C8 C7 H7 120.1 N2 C8 H8A 119.9 C7 C8 N2 120.2(3) C7 C8 H8A 119.9 C7 C8 H8B 119.9 C7 C8 C4B 120.2(3) C4B C8 H8B 119.9 N1 C9 H9 118.6 N1 C9 C10 122.8(3) C10 C9 H9 118.6 C9 C10 H10 120.6 C9 C10 C11 118.8(3) C11 C10 H10 120.6 C10 C11 H11 120.7 C12 C11 C10 118.6(3) C12 C11 H11 120.7 C11 C12 H12 120.3 C13 C12 C11 119.4(3) C13 C12 H12 120.3 N1 C13 C12 122.5(3) N1 C13 H13 118.7 C12 C13 H13 118.7 O5 C4 N2 118.4(2) O5 C4 C5 120.0(2) N2 C4 C5 121.5(2) O4 C4B N2B 118.9(2) O4 C4B C8 122.2(2) N2B C4B C8 118.9(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Re1 O4 2.1318(18) Re1 O5 2.1302(18) Re1 N1 2.215(2) Re1 C1 1.923(3) Re1 C2 1.906(3) Re1 C3 1.901(3) O1 C1 1.147(3) O2 C2 1.158(3) O3 C3 1.160(3) O4 N2 1.313(3) O4 C4B 1.313(3) O5 N2B 1.335(3) O5 C4 1.335(3) N1 C9 1.345(3) N1 C13 1.348(3) N2 C8 1.390(4) N2 C4 1.362(3) N2B C5 1.380(4) N2B C4B 1.362(3) C5 H5A 0.9500 C5 H5B 0.9500 C5 C6 1.364(4) C5 C4 1.380(4) C6 H6 0.9500 C6 C7 1.398(4) C7 H7 0.9500 C7 C8 1.374(4) C8 H8A 0.9500 C8 H8B 0.9500 C8 C4B 1.390(4) C9 H9 0.9500 C9 C10 1.383(4) C10 H10 0.9500 C10 C11 1.388(4) C11 H11 0.9500 C11 C12 1.382(4) C12 H12 0.9500 C12 C13 1.376(4) C13 H13 0.9500