#------------------------------------------------------------------------------ #$Date: 2019-12-13 03:54:52 +0200 (Fri, 13 Dec 2019) $ #$Revision: 245035 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/65/1556539.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_1556539 loop_ _publ_author_name 'Morrison, Christine N.' 'Prosser, Kathleen E.' 'Stokes, Ryjul W.' 'Cordes, Anna L.' '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_name_full 'Chemical Science' _journal_paper_doi 10.1039/C9SC05586J _journal_year 2020 _chemical_formula_moiety 'C20 H14 N O5 Re, 0.5(C H2 Cl2)' _chemical_formula_sum 'C20.5 H15 Cl N O5 Re' _chemical_formula_weight 576.98 _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 105.388(7) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 20.753(2) _cell_length_b 7.0352(8) _cell_length_c 13.7941(18) _cell_measurement_reflns_used 4183 _cell_measurement_temperature 100.0 _cell_measurement_theta_max 21.846 _cell_measurement_theta_min 3.054 _cell_volume 1941.8(4) _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 0.993 _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 0.0959 _diffrn_reflns_av_unetI/netI 0.0639 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 26253 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 25.381 _diffrn_reflns_theta_min 2.036 _diffrn_source 'sealed tube' _diffrn_source_type fine-focus _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 6.428 _exptl_absorpt_correction_T_max 0.0439 _exptl_absorpt_correction_T_min 0.0166 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1275 before and 0.0802 after correction. The Ratio of minimum to maximum transmission is 0.3781. 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 1.974 _exptl_crystal_description Block _exptl_crystal_F_000 1108 _exptl_crystal_size_max 0.153 _exptl_crystal_size_mid 0.147 _exptl_crystal_size_min 0.136 _refine_diff_density_max 0.923 _refine_diff_density_min -1.342 _refine_diff_density_rms 0.165 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 267 _refine_ls_number_reflns 3563 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.056 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0376 _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^)+(0.0238P)^2^+4.8116P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0759 _refine_ls_wR_factor_ref 0.0815 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2886 _reflns_number_total 3563 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc05586j2.cif _cod_data_source_block K11 _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 ; _cod_original_formula_sum 'C20.50 H15 Cl N O5 Re' _cod_database_code 1556539 _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 0.475 _shelx_estimated_absorpt_t_min 0.440 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances Cl1S-C1S 1.8 with sigma of 0.02 3. Uiso/Uaniso restraints and constraints Uanis(Re1B) = Uanis(Re1) 4. Others Sof(Re1B)=1-FVAR(1) Sof(Re1)=FVAR(1) Fixed Sof: C1S(0.5) H1SA(0.5) H1SB(0.5) 5.a Secondary CH2 refined with riding coordinates: C1S(H1SA,H1SB) 5.b Aromatic/amide H refined with riding coordinates: C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20) 5.c Idealised Me refined as rotating group: C4(H4A,H4B,H4C) ; _shelx_res_file ; TITL cm34_a.res in P2(1)/c cm34.res created by SHELXL-2018/3 at 14:28:34 on 04-Jun-2018 REM Old TITL CM34 in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.083, Rweak 0.006, Alpha 0.046 REM 0.300 for 315 systematic absences, Orientation as input REM Formula found by SHELXT: C20 N O6 Re1B CELL 0.71073 20.7534 7.0352 13.7941 90 105.388 90 ZERR 4 0.0024 0.0008 0.0018 0 0.007 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Cl N O Re UNIT 82 60 4 4 20 4 EQIV $1 1-X,-1-Y,1-Z DFIX 1.8 Cl1S C1S EADP Re1B Re1 L.S. 10 PLAN 20 SIZE 0.153 0.147 0.136 TEMP -173.15 FREE C1S C1S_$1 BOND list 4 fmap 2 ACTA 50 OMIT 1 0 0 REM REM REM WGHT 0.023800 4.811600 FVAR 0.23397 0.98514 PART 1 RE1 6 0.835476 0.781230 0.552715 21.00000 0.02454 0.02074 = 0.01740 0.00025 0.00557 -0.00117 O1 5 0.770658 1.034495 0.683005 11.00000 0.04152 0.03864 = 0.03009 -0.00802 0.01576 0.00323 O2 5 0.898372 0.534144 0.736196 11.00000 0.03690 0.03108 = 0.02186 0.00592 0.00576 -0.00167 O3 5 0.957160 1.045608 0.615673 11.00000 0.03187 0.03581 = 0.02176 -0.00311 0.00293 -0.01403 O4 5 0.753576 0.598756 0.499928 11.00000 0.02878 0.02428 = 0.02398 0.00062 0.00619 -0.00398 O5 5 0.793560 0.924252 0.413871 11.00000 0.03012 0.02551 = 0.01991 0.00427 0.00513 -0.00153 N1 4 0.881399 0.596572 0.459790 11.00000 0.03163 0.01829 = 0.01363 -0.00290 0.00495 -0.00167 C1 1 0.793572 0.938540 0.632047 11.00000 0.03180 0.03218 = 0.02142 0.00811 -0.00194 -0.00609 C2 1 0.873721 0.632497 0.667283 11.00000 0.04042 0.01633 = 0.02862 -0.00762 0.01547 -0.00592 C3 1 0.911389 0.945216 0.592645 11.00000 0.03185 0.02863 = 0.01376 0.00662 0.00645 0.01173 C4 1 0.731847 1.026890 0.255244 11.00000 0.03198 0.02947 = 0.02986 0.01062 0.00202 0.00282 AFIX 137 H4A 2 0.687413 1.083651 0.244913 11.00000 -1.50000 H4B 2 0.734453 0.960756 0.193872 11.00000 -1.50000 H4C 2 0.765845 1.127057 0.271152 11.00000 -1.50000 AFIX 0 C5 1 0.743914 0.886977 0.341226 11.00000 0.03095 0.03110 = 0.02742 -0.00213 0.01158 -0.00169 C6 1 0.700687 0.725640 0.335774 11.00000 0.02684 0.02587 = 0.02656 -0.00120 0.00823 0.00088 C7 1 0.708965 0.589510 0.413248 11.00000 0.02380 0.03146 = 0.02145 -0.00317 0.00365 0.00224 C8 1 0.666322 0.423422 0.398878 11.00000 0.02899 0.02039 = 0.03031 -0.00544 0.00870 -0.00060 C9 1 0.614332 0.401275 0.308430 11.00000 0.02230 0.03684 = 0.03422 -0.00238 0.00137 -0.00004 C10 1 0.605768 0.544114 0.232736 11.00000 0.02356 0.04209 = 0.03370 -0.00525 -0.00454 -0.00167 AFIX 43 H10 2 0.570525 0.532752 0.172884 11.00000 -1.20000 AFIX 0 C11 1 0.647178 0.695204 0.245213 11.00000 0.03511 0.03546 = 0.03460 0.00303 0.00502 0.00484 AFIX 43 H11 2 0.641023 0.785608 0.192382 11.00000 -1.20000 AFIX 0 C12 1 0.675605 0.278871 0.471864 11.00000 0.02908 0.03076 = 0.03028 -0.00517 0.00812 0.00053 AFIX 43 H12 2 0.709786 0.291982 0.532839 11.00000 -1.20000 AFIX 0 C13 1 0.635659 0.117442 0.456266 11.00000 0.02941 0.03912 = 0.04976 0.00209 0.00958 -0.00671 AFIX 43 H13 2 0.643311 0.020226 0.505814 11.00000 -1.20000 AFIX 0 C14 1 0.584541 0.097644 0.368440 11.00000 0.03361 0.03474 = 0.05117 0.00076 0.00718 -0.01047 AFIX 43 H14 2 0.556852 -0.012014 0.358814 11.00000 -1.20000 AFIX 0 C15 1 0.573615 0.237839 0.294274 11.00000 0.03562 0.04322 = 0.04566 -0.01251 0.00092 -0.00748 AFIX 43 H15 2 0.538730 0.223113 0.234239 11.00000 -1.20000 AFIX 0 C16 1 0.867775 0.408379 0.450306 11.00000 0.02770 0.02237 = 0.01902 -0.00400 0.00101 -0.00508 AFIX 43 H16 2 0.836012 0.356508 0.481447 11.00000 -1.20000 AFIX 0 C17 1 0.898811 0.288551 0.396404 11.00000 0.02836 0.01974 = 0.02860 -0.00407 0.00036 0.00219 AFIX 43 H17 2 0.888528 0.156735 0.391307 11.00000 -1.20000 AFIX 0 C18 1 0.944843 0.363099 0.350225 11.00000 0.03419 0.02703 = 0.01840 0.00624 0.01112 0.00674 AFIX 43 H18 2 0.966371 0.283617 0.312727 11.00000 -1.20000 AFIX 0 C19 1 0.958884 0.555048 0.359670 11.00000 0.01845 0.03874 = 0.02303 0.00454 0.00416 0.00034 AFIX 43 H19 2 0.990299 0.609941 0.328823 11.00000 -1.20000 AFIX 0 C20 1 0.926827 0.664903 0.414160 11.00000 0.03024 0.01970 = 0.01981 -0.00118 0.00683 -0.00149 AFIX 43 H20 2 0.937036 0.796716 0.420331 11.00000 -1.20000 AFIX 0 PART 0 CL1S 3 0.537273 -0.326052 0.489859 11.00000 0.07430 0.09487 = 0.05558 -0.01621 0.01562 -0.02874 C1S 1 0.525303 -0.515477 0.553762 10.50000 0.12016 0.06130 = 0.08851 0.02506 0.00831 -0.04004 AFIX 23 H1SA 2 0.520125 -0.468600 0.618947 10.50000 -1.20000 H1SB 2 0.567512 -0.588825 0.568995 10.50000 -1.20000 AFIX 0 PART 2 RE1B 6 0.830118 0.231754 0.560248 -21.00000 0.02454 0.02074 = 0.01740 0.00025 0.00557 -0.00117 HKLF 4 REM cm34_a.res in P2(1)/c REM wR2 = 0.0815, GooF = S = 1.049, Restrained GooF = 1.056 for all data REM R1 = 0.0376 for 2886 Fo > 4sig(Fo) and 0.0535 for all 3563 data REM 267 parameters refined using 1 restraints END WGHT 0.0238 4.8010 REM Highest difference peak 0.923, deepest hole -1.342, 1-sigma level 0.165 Q1 1 0.8820 0.7841 0.5926 11.00000 0.05 0.92 Q2 1 0.8162 0.6249 0.5998 11.00000 0.05 0.88 Q3 1 0.8427 0.9354 0.5783 11.00000 0.05 0.85 Q4 1 0.7821 0.7509 0.5218 11.00000 0.05 0.77 Q5 1 0.5288 -0.4563 0.5400 11.00000 0.05 0.77 Q6 1 0.5169 0.2739 0.2229 11.00000 0.05 0.69 Q7 1 0.8437 0.2810 0.6040 11.00000 0.05 0.67 Q8 1 0.8789 0.6445 0.5203 11.00000 0.05 0.66 Q9 1 0.5896 0.5111 0.4192 11.00000 0.05 0.59 Q10 1 0.8354 0.6198 0.4877 11.00000 0.05 0.58 Q11 1 0.7682 0.8346 0.5766 11.00000 0.05 0.57 Q12 1 0.5355 -0.5568 0.4847 11.00000 0.05 0.57 Q13 1 0.8457 1.1968 0.2567 11.00000 0.05 0.56 Q14 1 1.0240 0.5187 0.2621 11.00000 0.05 0.56 Q15 1 0.6293 -0.4754 0.5259 11.00000 0.05 0.55 Q16 1 0.9420 0.7734 0.6232 11.00000 0.05 0.54 Q17 1 1.0375 0.5090 0.3992 11.00000 0.05 0.54 Q18 1 0.7893 1.0493 0.4210 11.00000 0.05 0.53 Q19 1 0.6757 0.1349 0.4789 11.00000 0.05 0.53 Q20 1 0.9114 0.1149 0.4592 11.00000 0.05 0.53 ; _shelx_res_checksum 67226 _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 0.83548(2) 0.78123(4) 0.55271(2) 0.02089(10) Uani 0.9851(7) 1 d . P A 1 O1 O 0.7707(3) 1.0345(7) 0.6830(4) 0.0356(13) Uani 1 1 d . . A 1 O2 O 0.8984(3) 0.5341(7) 0.7362(4) 0.0303(12) Uani 1 1 d . . A 1 O3 O 0.9572(3) 1.0456(7) 0.6157(4) 0.0306(12) Uani 1 1 d . . A 1 O4 O 0.7536(2) 0.5988(6) 0.4999(4) 0.0258(11) Uani 1 1 d . . A 1 O5 O 0.7936(2) 0.9243(6) 0.4139(4) 0.0255(11) Uani 1 1 d . . A 1 N1 N 0.8814(3) 0.5966(8) 0.4598(4) 0.0214(13) Uani 1 1 d . . A 1 C1 C 0.7936(4) 0.9385(11) 0.6320(6) 0.0302(18) Uani 1 1 d . . A 1 C2 C 0.8737(4) 0.6325(10) 0.6673(6) 0.0273(17) Uani 1 1 d . . A 1 C3 C 0.9114(4) 0.9452(10) 0.5926(5) 0.0247(17) Uani 1 1 d . . A 1 C4 C 0.7318(4) 1.0269(10) 0.2552(6) 0.0316(18) Uani 1 1 d . . A 1 H4A H 0.687413 1.083651 0.244913 0.047 Uiso 1 1 calc GR . A 1 H4B H 0.734453 0.960756 0.193872 0.047 Uiso 1 1 calc GR . A 1 H4C H 0.765845 1.127057 0.271152 0.047 Uiso 1 1 calc GR . A 1 C5 C 0.7439(4) 0.8870(10) 0.3412(6) 0.0291(18) Uani 1 1 d . . A 1 C6 C 0.7007(4) 0.7256(10) 0.3358(5) 0.0262(16) Uani 1 1 d . . A 1 C7 C 0.7090(4) 0.5895(10) 0.4132(5) 0.0260(17) Uani 1 1 d . . A 1 C8 C 0.6663(4) 0.4234(10) 0.3989(6) 0.0264(17) Uani 1 1 d . . A 1 C9 C 0.6143(4) 0.4013(11) 0.3084(6) 0.0323(19) Uani 1 1 d . . A 1 C10 C 0.6058(4) 0.5441(11) 0.2327(6) 0.035(2) Uani 1 1 d . . A 1 H10 H 0.570525 0.532752 0.172884 0.043 Uiso 1 1 calc R . A 1 C11 C 0.6472(4) 0.6952(11) 0.2452(6) 0.0359(19) Uani 1 1 d . . A 1 H11 H 0.641023 0.785608 0.192382 0.043 Uiso 1 1 calc R . A 1 C12 C 0.6756(4) 0.2789(10) 0.4719(6) 0.0300(18) Uani 1 1 d . . A 1 H12 H 0.709786 0.291982 0.532839 0.036 Uiso 1 1 calc R . A 1 C13 C 0.6357(4) 0.1174(12) 0.4563(7) 0.040(2) Uani 1 1 d . . A 1 H13 H 0.643311 0.020226 0.505814 0.048 Uiso 1 1 calc R . A 1 C14 C 0.5845(4) 0.0976(12) 0.3684(7) 0.041(2) Uani 1 1 d . . A 1 H14 H 0.556852 -0.012014 0.358814 0.049 Uiso 1 1 calc R . A 1 C15 C 0.5736(4) 0.2378(12) 0.2943(7) 0.043(2) Uani 1 1 d . . A 1 H15 H 0.538730 0.223113 0.234239 0.052 Uiso 1 1 calc R . A 1 C16 C 0.8678(4) 0.4084(10) 0.4503(5) 0.0240(16) Uani 1 1 d . . A 1 H16 H 0.836012 0.356508 0.481447 0.029 Uiso 1 1 calc R . A 1 C17 C 0.8988(3) 0.2886(10) 0.3964(5) 0.0269(16) Uani 1 1 d . . A 1 H17 H 0.888528 0.156735 0.391307 0.032 Uiso 1 1 calc R . A 1 C18 C 0.9448(4) 0.3631(10) 0.3502(5) 0.0257(17) Uani 1 1 d . . A 1 H18 H 0.966371 0.283617 0.312727 0.031 Uiso 1 1 calc R . A 1 C19 C 0.9589(3) 0.5550(10) 0.3597(5) 0.0270(17) Uani 1 1 d . . A 1 H19 H 0.990299 0.609941 0.328823 0.032 Uiso 1 1 calc R . A 1 C20 C 0.9268(3) 0.6649(10) 0.4142(5) 0.0232(16) Uani 1 1 d . . A 1 H20 H 0.937036 0.796716 0.420331 0.028 Uiso 1 1 calc R . A 1 Cl1S Cl 0.53727(15) -0.3261(4) 0.4899(2) 0.0752(8) Uani 1 1 d D . . . C1S C 0.5253(14) -0.515(3) 0.5538(17) 0.094(9) Uani 0.5 1 d D P . . H1SA H 0.520125 -0.468600 0.618947 0.112 Uiso 0.5 1 calc R P . . H1SB H 0.567512 -0.588825 0.568995 0.112 Uiso 0.5 1 calc R P . . Re1B Re 0.8301(9) 0.232(3) 0.5602(14) 0.02089(10) Uani 0.0149(7) 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 0.02454(17) 0.02074(16) 0.01740(16) 0.00025(13) 0.00557(11) -0.00117(13) O1 0.042(3) 0.039(3) 0.030(3) -0.008(3) 0.016(3) 0.003(3) O2 0.037(3) 0.031(3) 0.022(3) 0.006(2) 0.006(3) -0.002(2) O3 0.032(3) 0.036(3) 0.022(3) -0.003(2) 0.003(2) -0.014(3) O4 0.029(3) 0.024(3) 0.024(3) 0.001(2) 0.006(2) -0.004(2) O5 0.030(3) 0.026(3) 0.020(3) 0.004(2) 0.005(2) -0.002(2) N1 0.032(3) 0.018(3) 0.014(3) -0.003(2) 0.005(3) -0.002(3) C1 0.032(4) 0.032(4) 0.021(4) 0.008(3) -0.002(4) -0.006(4) C2 0.040(5) 0.016(4) 0.029(5) -0.008(3) 0.015(4) -0.006(3) C3 0.032(5) 0.029(4) 0.014(4) 0.007(3) 0.006(3) 0.012(4) C4 0.032(5) 0.029(4) 0.030(5) 0.011(3) 0.002(4) 0.003(3) C5 0.031(5) 0.031(5) 0.027(5) -0.002(3) 0.012(4) -0.002(3) C6 0.027(4) 0.026(4) 0.027(4) -0.001(3) 0.008(3) 0.001(3) C7 0.024(4) 0.031(4) 0.021(4) -0.003(3) 0.004(3) 0.002(3) C8 0.029(4) 0.020(4) 0.030(5) -0.005(3) 0.009(4) -0.001(3) C9 0.022(4) 0.037(5) 0.034(5) -0.002(4) 0.001(4) 0.000(3) C10 0.024(4) 0.042(5) 0.034(5) -0.005(4) -0.005(4) -0.002(4) C11 0.035(5) 0.035(5) 0.035(5) 0.003(4) 0.005(4) 0.005(4) C12 0.029(4) 0.031(4) 0.030(5) -0.005(3) 0.008(3) 0.001(3) C13 0.029(5) 0.039(5) 0.050(6) 0.002(4) 0.010(4) -0.007(4) C14 0.034(5) 0.035(5) 0.051(6) 0.001(4) 0.007(4) -0.010(4) C15 0.036(5) 0.043(5) 0.046(6) -0.013(4) 0.001(4) -0.007(4) C16 0.028(4) 0.022(4) 0.019(4) -0.004(3) 0.001(3) -0.005(3) C17 0.028(4) 0.020(4) 0.029(4) -0.004(3) 0.000(3) 0.002(3) C18 0.034(4) 0.027(4) 0.018(4) 0.006(3) 0.011(3) 0.007(3) C19 0.018(4) 0.039(5) 0.023(4) 0.005(3) 0.004(3) 0.000(3) C20 0.030(4) 0.020(4) 0.020(4) -0.001(3) 0.007(3) -0.001(3) Cl1S 0.0743(19) 0.095(2) 0.0556(18) -0.0162(15) 0.0156(15) -0.0287(16) C1S 0.12(2) 0.061(15) 0.09(2) 0.025(14) 0.008(16) -0.040(15) Re1B 0.02454(17) 0.02074(16) 0.01740(16) 0.00025(13) 0.00557(11) -0.00117(13) 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' Cl Cl 0.1484 0.1585 '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 _geom_angle_site_symmetry_3 O4 Re1 O5 82.96(18) . O4 Re1 N1 82.73(19) . O5 Re1 N1 83.83(19) . C1 Re1 O4 95.9(3) . C1 Re1 O5 95.8(2) . C1 Re1 N1 178.6(3) . C2 Re1 O4 94.2(3) . C2 Re1 O5 174.0(2) . C2 Re1 N1 90.5(3) . C2 Re1 C1 89.8(3) . C2 Re1 C3 87.8(3) . C3 Re1 O4 176.3(2) . C3 Re1 O5 94.7(2) . C3 Re1 N1 94.2(3) . C3 Re1 C1 87.2(3) . C7 O4 Re1 131.3(4) . C5 O5 Re1 132.0(5) . C16 N1 Re1 121.3(4) . C16 N1 C20 117.1(6) . C20 N1 Re1 121.4(4) . O1 C1 Re1 177.2(7) . O2 C2 Re1 177.2(6) . O3 C3 Re1 179.2(7) . O5 C5 C4 114.8(6) . O5 C5 C6 125.0(7) . C6 C5 C4 120.2(7) . C5 C6 C11 119.1(7) . C7 C6 C5 123.2(7) . C7 C6 C11 117.6(7) . O4 C7 C6 125.0(7) . O4 C7 C8 115.2(6) . C6 C7 C8 119.8(7) . C9 C8 C7 120.1(7) . C12 C8 C7 121.5(7) . C12 C8 C9 118.4(7) . C8 C9 C10 118.8(7) . C15 C9 C8 119.8(7) . C15 C9 C10 121.3(7) . C11 C10 C9 120.7(8) . C10 C11 C6 122.9(7) . C13 C12 C8 121.1(7) . C12 C13 C14 120.2(8) . C13 C14 C15 120.4(8) . C14 C15 C9 120.0(8) . N1 C16 C17 122.0(7) . C18 C17 C16 119.4(7) . C19 C18 C17 118.8(7) . C20 C19 C18 118.9(7) . N1 C20 C19 123.7(6) . C1S Cl1S C1S 56.6(13) 3_646 Cl1S C1S Cl1S 123.4(13) 3_646 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Re1 O4 2.100(5) . Re1 O5 2.134(5) . Re1 N1 2.211(5) . Re1 C1 1.919(8) . Re1 C2 1.886(8) . Re1 C3 1.912(8) . O1 C1 1.163(9) . O2 C2 1.177(9) . O3 C3 1.158(8) . O4 C7 1.305(8) . O5 C5 1.260(8) . N1 C16 1.353(8) . N1 C20 1.353(8) . C4 C5 1.510(10) . C5 C6 1.436(10) . C6 C7 1.411(10) . C6 C11 1.450(10) . C7 C8 1.447(10) . C8 C9 1.425(10) . C8 C12 1.408(10) . C9 C10 1.426(11) . C9 C15 1.409(11) . C10 C11 1.349(10) . C12 C13 1.389(10) . C13 C14 1.389(11) . C14 C15 1.396(12) . C16 C17 1.390(9) . C17 C18 1.384(9) . C18 C19 1.380(10) . C19 C20 1.368(9) . Cl1S C1S 1.653(14) . Cl1S C1S 1.70(2) 3_646