#------------------------------------------------------------------------------ #$Date: 2020-03-05 01:50:51 +0200 (Thu, 05 Mar 2020) $ #$Revision: 248877 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/65/1556538.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_1556538 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_paper_doi 10.1039/C9SC05586J _journal_volume 11 _journal_year 2020 _chemical_formula_moiety 'C15 H12 N O4 Re S' _chemical_formula_sum 'C15 H12 N O4 Re S' _chemical_formula_weight 488.52 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 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 96.365(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.5304(5) _cell_length_b 8.1560(5) _cell_length_c 22.7941(15) _cell_measurement_reflns_used 6720 _cell_measurement_temperature 100.0 _cell_measurement_theta_max 25.959 _cell_measurement_theta_min 2.654 _cell_volume 1576.10(17) _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 0.999 _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 0.0421 _diffrn_reflns_av_unetI/netI 0.0297 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 21549 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 26.379 _diffrn_reflns_theta_min 2.470 _diffrn_source 'sealed tube' _diffrn_source_type fine-focus _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 7.858 _exptl_absorpt_correction_T_max 0.2602 _exptl_absorpt_correction_T_min 0.2290 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0484 before and 0.0433 after correction. The Ratio of minimum to maximum transmission is 0.8801. 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 2.059 _exptl_crystal_description Block _exptl_crystal_F_000 928 _exptl_crystal_size_max 0.087 _exptl_crystal_size_mid 0.065 _exptl_crystal_size_min 0.063 _refine_diff_density_max 0.465 _refine_diff_density_min -0.821 _refine_diff_density_rms 0.116 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 200 _refine_ls_number_reflns 3228 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.051 _refine_ls_R_factor_all 0.0285 _refine_ls_R_factor_gt 0.0207 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0136P)^2^+0.4010P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0372 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2783 _reflns_number_total 3228 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc05586j2.cif _cod_data_source_block K12 _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. ; _cod_database_code 1556538 _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 0.637 _shelx_estimated_absorpt_t_min 0.548 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15) 2.b Idealised Me refined as rotating group: C10(H10A,H10B,H10C) ; _shelx_res_file ; TITL cm36_a.res in P2(1)/n cm36.res created by SHELXL-2018/3 at 14:44:43 on 04-Jun-2018 REM Old TITL CM36 in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.051, Rweak 0.002, Alpha 0.040 REM 0.473 for 242 systematic absences, Orientation as input REM Formula found by SHELXT: C15 N O4 S Re CELL 0.71073 8.5304 8.156 22.7941 90 96.365 90 ZERR 4 0.0005 0.0005 0.0015 0 0.002 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O Re S UNIT 60 48 4 16 4 4 L.S. 10 PLAN 20 SIZE 0.087 0.065 0.063 TEMP -173.15 BOND list 4 fmap 2 ACTA 50 REM REM REM WGHT 0.013600 0.401000 FVAR 0.26754 RE1 5 0.784992 0.630308 0.414567 11.00000 0.01621 0.01035 = 0.01418 0.00129 -0.00009 -0.00126 S1 6 0.798359 0.720647 0.311159 11.00000 0.02001 0.01266 = 0.01720 0.00218 0.00160 -0.00218 O1 4 0.997247 0.328294 0.406518 11.00000 0.03127 0.02026 = 0.02380 -0.00193 -0.00259 0.00925 O2 4 1.072120 0.817772 0.473286 11.00000 0.02371 0.02849 = 0.02844 -0.00172 -0.00366 -0.01014 O3 4 0.708444 0.503772 0.535221 11.00000 0.03192 0.02131 = 0.02002 0.00567 0.00743 0.00012 O4 4 0.575009 0.523175 0.374510 11.00000 0.02054 0.01238 = 0.01754 0.00207 -0.00180 -0.00503 N1 3 0.633931 0.852134 0.415439 11.00000 0.01875 0.01066 = 0.01600 0.00259 0.00121 -0.00189 C1 1 0.915688 0.442147 0.409193 11.00000 0.02275 0.01835 = 0.01127 0.00234 -0.00320 -0.00677 C2 1 0.964949 0.746799 0.451249 11.00000 0.02093 0.01635 = 0.01672 0.00549 0.00341 0.00307 C3 1 0.738924 0.554259 0.491023 11.00000 0.01837 0.00831 = 0.02365 0.00073 -0.00112 0.00045 C4 1 0.529337 0.540480 0.317580 11.00000 0.01837 0.01125 = 0.01815 -0.00066 0.00096 0.00314 C5 1 0.620659 0.626902 0.279625 11.00000 0.01732 0.01354 = 0.01731 0.00054 -0.00125 0.00070 C6 1 0.570693 0.644338 0.219584 11.00000 0.02513 0.01579 = 0.01856 0.00275 0.00231 0.00479 AFIX 43 H6 2 0.633471 0.703434 0.194899 11.00000 -1.20000 AFIX 0 C7 1 0.429063 0.575101 0.196064 11.00000 0.02719 0.02438 = 0.01881 -0.00165 -0.00794 0.00409 AFIX 43 H7 2 0.394839 0.585175 0.155122 11.00000 -1.20000 AFIX 0 C8 1 0.337493 0.490736 0.232945 11.00000 0.02267 0.01993 = 0.02853 -0.00105 -0.00528 0.00105 AFIX 43 H8 2 0.239824 0.444453 0.216926 11.00000 -1.20000 AFIX 0 C9 1 0.386006 0.473183 0.292258 11.00000 0.01915 0.01544 = 0.02762 0.00227 0.00200 0.00006 AFIX 43 H9 2 0.321491 0.414605 0.316450 11.00000 -1.20000 AFIX 0 C10 1 0.949465 0.608885 0.278064 11.00000 0.02325 0.02705 = 0.02573 0.00188 0.00957 0.00179 AFIX 137 H10A 2 1.053606 0.641124 0.297052 11.00000 -1.50000 H10B 2 0.942180 0.634103 0.235813 11.00000 -1.50000 H10C 2 0.934412 0.490926 0.283410 11.00000 -1.50000 AFIX 0 C11 1 0.692548 1.003193 0.407686 11.00000 0.01906 0.01590 = 0.02127 0.00207 0.00184 -0.00512 AFIX 43 H11 2 0.800860 1.014097 0.402233 11.00000 -1.20000 AFIX 0 C12 1 0.600528 1.142599 0.407401 11.00000 0.02708 0.01224 = 0.02560 0.00005 0.00041 -0.00365 AFIX 43 H12 2 0.645188 1.247106 0.401329 11.00000 -1.20000 AFIX 0 C13 1 0.444457 1.129437 0.415921 11.00000 0.03224 0.01737 = 0.01809 0.00372 0.00211 0.01016 AFIX 43 H13 2 0.379201 1.223902 0.415551 11.00000 -1.20000 AFIX 0 C14 1 0.384385 0.975178 0.425069 11.00000 0.01983 0.02694 = 0.02347 0.00673 0.00499 0.00259 AFIX 43 H14 2 0.277337 0.962618 0.432100 11.00000 -1.20000 AFIX 0 C15 1 0.480827 0.839531 0.423928 11.00000 0.01821 0.02002 = 0.02058 0.00459 0.00068 -0.00292 AFIX 43 H15 2 0.437688 0.733915 0.429310 11.00000 -1.20000 AFIX 0 HKLF 4 REM cm36_a.res in P2(1)/n REM wR2 = 0.0372, GooF = S = 1.051, Restrained GooF = 1.051 for all data REM R1 = 0.0207 for 2783 Fo > 4sig(Fo) and 0.0285 for all 3228 data REM 200 parameters refined using 0 restraints END WGHT 0.0136 0.4011 REM Highest difference peak 0.465, deepest hole -0.821, 1-sigma level 0.116 Q1 1 0.8748 0.7038 0.3978 11.00000 0.05 0.47 Q2 1 0.2918 0.9390 0.4681 11.00000 0.05 0.46 Q3 1 0.3214 0.8689 0.4273 11.00000 0.05 0.44 Q4 1 0.3826 0.7054 0.2096 11.00000 0.05 0.43 Q5 1 0.6239 1.1863 0.4026 11.00000 0.05 0.43 Q6 1 0.5384 1.1418 0.4343 11.00000 0.05 0.42 Q7 1 0.3858 0.5011 0.3450 11.00000 0.05 0.40 Q8 1 0.8220 0.4441 0.6119 11.00000 0.05 0.39 Q9 1 0.8581 0.5675 0.3863 11.00000 0.05 0.39 Q10 1 0.0451 0.4086 0.1897 11.00000 0.05 0.38 Q11 1 0.4645 0.4824 0.3028 11.00000 0.05 0.38 Q12 1 0.6650 0.4133 0.3115 11.00000 0.05 0.37 Q13 1 0.2460 0.6296 0.2120 11.00000 0.05 0.36 Q14 1 0.6956 0.6451 0.2926 11.00000 0.05 0.36 Q15 1 0.6665 1.0937 0.4258 11.00000 0.05 0.36 Q16 1 0.3317 1.2749 0.3598 11.00000 0.05 0.36 Q17 1 0.8199 0.8836 0.2631 11.00000 0.05 0.36 Q18 1 0.3647 1.0361 0.4582 11.00000 0.05 0.36 Q19 1 0.4037 0.4624 0.2579 11.00000 0.05 0.36 Q20 1 0.4395 0.9218 0.4373 11.00000 0.05 0.35 ; _shelx_res_checksum 9699 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_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' 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 Re1 Re 0.78499(2) 0.63031(2) 0.41457(2) 0.01371(5) Uani 1 1 d . S1 S 0.79836(10) 0.72065(10) 0.31116(4) 0.01666(19) Uani 1 1 d . O1 O 0.9972(3) 0.3283(3) 0.40652(11) 0.0255(6) Uani 1 1 d . O2 O 1.0721(3) 0.8178(3) 0.47329(11) 0.0274(6) Uani 1 1 d . O3 O 0.7084(3) 0.5038(3) 0.53522(10) 0.0241(6) Uani 1 1 d . O4 O 0.5750(3) 0.5232(3) 0.37451(10) 0.0171(5) Uani 1 1 d . N1 N 0.6339(3) 0.8521(3) 0.41544(12) 0.0152(6) Uani 1 1 d . C1 C 0.9157(4) 0.4421(4) 0.40919(14) 0.0178(8) Uani 1 1 d . C2 C 0.9649(4) 0.7468(4) 0.45125(15) 0.0179(8) Uani 1 1 d . C3 C 0.7389(4) 0.5543(4) 0.49102(16) 0.0170(8) Uani 1 1 d . C4 C 0.5293(4) 0.5405(4) 0.31758(15) 0.0160(7) Uani 1 1 d . C5 C 0.6207(4) 0.6269(4) 0.27963(14) 0.0163(7) Uani 1 1 d . C6 C 0.5707(4) 0.6443(4) 0.21958(15) 0.0198(8) Uani 1 1 d . H6 H 0.633471 0.703434 0.194899 0.024 Uiso 1 1 calc R C7 C 0.4291(4) 0.5751(4) 0.19606(16) 0.0242(9) Uani 1 1 d . H7 H 0.394839 0.585175 0.155122 0.029 Uiso 1 1 calc R C8 C 0.3375(4) 0.4907(4) 0.23295(16) 0.0243(8) Uani 1 1 d . H8 H 0.239824 0.444453 0.216926 0.029 Uiso 1 1 calc R C9 C 0.3860(4) 0.4732(4) 0.29226(16) 0.0208(8) Uani 1 1 d . H9 H 0.321491 0.414605 0.316450 0.025 Uiso 1 1 calc R C10 C 0.9495(4) 0.6089(4) 0.27806(16) 0.0248(8) Uani 1 1 d . H10A H 1.053606 0.641124 0.297052 0.037 Uiso 1 1 calc GR H10B H 0.942180 0.634103 0.235813 0.037 Uiso 1 1 calc GR H10C H 0.934412 0.490926 0.283410 0.037 Uiso 1 1 calc GR C11 C 0.6925(4) 1.0032(4) 0.40769(14) 0.0188(8) Uani 1 1 d . H11 H 0.800860 1.014097 0.402233 0.023 Uiso 1 1 calc R C12 C 0.6005(4) 1.1426(4) 0.40740(15) 0.0218(8) Uani 1 1 d . H12 H 0.645188 1.247106 0.401329 0.026 Uiso 1 1 calc R C13 C 0.4445(4) 1.1294(4) 0.41592(15) 0.0226(8) Uani 1 1 d . H13 H 0.379201 1.223902 0.415551 0.027 Uiso 1 1 calc R C14 C 0.3844(4) 0.9752(4) 0.42507(15) 0.0232(8) Uani 1 1 d . H14 H 0.277337 0.962618 0.432100 0.028 Uiso 1 1 calc R C15 C 0.4808(4) 0.8395(4) 0.42393(15) 0.0197(8) Uani 1 1 d . H15 H 0.437688 0.733915 0.429310 0.024 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 0.01621(8) 0.01035(7) 0.01418(8) 0.00129(6) -0.00009(5) -0.00126(6) S1 0.0200(5) 0.0127(4) 0.0172(5) 0.0022(3) 0.0016(4) -0.0022(3) O1 0.0313(15) 0.0203(13) 0.0238(15) -0.0019(11) -0.0026(12) 0.0092(11) O2 0.0237(14) 0.0285(14) 0.0284(15) -0.0017(12) -0.0037(12) -0.0101(11) O3 0.0319(15) 0.0213(13) 0.0200(14) 0.0057(12) 0.0074(12) 0.0001(11) O4 0.0205(13) 0.0124(11) 0.0175(13) 0.0021(10) -0.0018(10) -0.0050(10) N1 0.0187(15) 0.0107(14) 0.0160(15) 0.0026(12) 0.0012(12) -0.0019(11) C1 0.023(2) 0.0183(18) 0.0113(18) 0.0023(14) -0.0032(15) -0.0068(16) C2 0.021(2) 0.0164(17) 0.0167(19) 0.0055(15) 0.0034(16) 0.0031(15) C3 0.0184(19) 0.0083(16) 0.024(2) 0.0007(15) -0.0011(16) 0.0004(14) C4 0.0184(18) 0.0113(16) 0.0182(19) -0.0007(14) 0.0010(15) 0.0031(14) C5 0.0173(17) 0.0135(16) 0.0173(18) 0.0005(15) -0.0013(14) 0.0007(15) C6 0.0251(19) 0.0158(17) 0.0186(19) 0.0028(15) 0.0023(16) 0.0048(16) C7 0.027(2) 0.0244(19) 0.019(2) -0.0016(16) -0.0079(17) 0.0041(16) C8 0.023(2) 0.0199(18) 0.029(2) -0.0010(17) -0.0053(17) 0.0011(16) C9 0.0191(19) 0.0154(17) 0.028(2) 0.0023(16) 0.0020(16) 0.0001(15) C10 0.023(2) 0.027(2) 0.026(2) 0.0019(18) 0.0096(16) 0.0018(17) C11 0.0191(19) 0.0159(17) 0.021(2) 0.0021(15) 0.0018(16) -0.0051(15) C12 0.027(2) 0.0122(17) 0.026(2) 0.0000(16) 0.0004(17) -0.0037(15) C13 0.032(2) 0.0174(17) 0.0181(19) 0.0037(16) 0.0021(16) 0.0102(17) C14 0.020(2) 0.027(2) 0.023(2) 0.0067(17) 0.0050(16) 0.0026(16) C15 0.0182(19) 0.0200(19) 0.021(2) 0.0046(15) 0.0007(16) -0.0029(14) 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' S S 0.1246 0.1234 '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 S1 80.68(6) O4 Re1 N1 82.85(9) N1 Re1 S1 81.65(7) C1 Re1 S1 95.11(10) C1 Re1 O4 96.50(11) C1 Re1 N1 176.75(12) C1 Re1 C2 88.93(14) C1 Re1 C3 88.76(13) C2 Re1 S1 98.52(10) C2 Re1 O4 174.56(11) C2 Re1 N1 91.70(12) C2 Re1 C3 89.93(14) C3 Re1 S1 170.76(10) C3 Re1 O4 90.55(11) C3 Re1 N1 94.43(11) C5 S1 Re1 97.43(11) C5 S1 C10 103.28(16) C10 S1 Re1 110.84(12) C4 O4 Re1 121.7(2) C11 N1 Re1 121.2(2) C15 N1 Re1 120.8(2) C15 N1 C11 117.9(3) O1 C1 Re1 179.0(3) O2 C2 Re1 179.4(3) O3 C3 Re1 177.2(3) O4 C4 C5 122.1(3) O4 C4 C9 120.7(3) C9 C4 C5 117.2(3) C4 C5 S1 118.0(2) C6 C5 S1 120.5(3) C6 C5 C4 121.4(3) C7 C6 C5 119.8(3) C6 C7 C8 119.4(3) C9 C8 C7 121.1(3) C8 C9 C4 121.1(3) N1 C11 C12 122.3(3) C13 C12 C11 119.7(3) C12 C13 C14 118.3(3) C15 C14 C13 119.6(3) N1 C15 C14 122.1(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Re1 S1 2.4842(9) Re1 O4 2.108(2) Re1 N1 2.223(3) Re1 C1 1.909(4) Re1 C2 1.917(4) Re1 C3 1.931(4) S1 C5 1.777(3) S1 C10 1.810(3) O1 C1 1.166(4) O2 C2 1.149(4) O3 C3 1.145(4) O4 C4 1.320(4) N1 C11 1.349(4) N1 C15 1.345(4) C4 C5 1.415(4) C4 C9 1.405(5) C5 C6 1.395(5) C6 C7 1.386(5) C7 C8 1.391(5) C8 C9 1.377(5) C11 C12 1.381(4) C12 C13 1.371(5) C13 C14 1.383(5) C14 C15 1.381(5)