#------------------------------------------------------------------------------ #$Date: 2019-12-13 03:54:52 +0200 (Fri, 13 Dec 2019) $ #$Revision: 245035 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/65/1556536.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_1556536 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_absolute_configuration ad _chemical_formula_moiety 'C15 H13 N2 O5 Re' _chemical_formula_sum 'C15 H13 N2 O5 Re' _chemical_formula_weight 487.47 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _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 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.3450(2) _cell_length_b 14.5492(5) _cell_length_c 16.7909(7) _cell_measurement_reflns_used 3384 _cell_measurement_temperature 100.0 _cell_measurement_theta_max 23.820 _cell_measurement_theta_min 2.426 _cell_volume 1550.05(10) _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 0.0536 _diffrn_reflns_av_unetI/netI 0.0444 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 17683 _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 26.396 _diffrn_reflns_theta_min 1.852 _diffrn_source 'sealed tube' _diffrn_source_type fine-focus _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 7.866 _exptl_absorpt_correction_T_max 0.0932 _exptl_absorpt_correction_T_min 0.0546 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0956 before and 0.0572 after correction. The Ratio of minimum to maximum transmission is 0.5858. 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 2.089 _exptl_crystal_description Rod _exptl_crystal_F_000 928 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM, hexanes' _exptl_crystal_size_max 0.213 _exptl_crystal_size_mid 0.145 _exptl_crystal_size_min 0.117 _refine_diff_density_max 0.494 _refine_diff_density_min -0.533 _refine_diff_density_rms 0.121 _refine_ls_abs_structure_details ; Flack x determined using 745 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.025(14) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 211 _refine_ls_number_reflns 3161 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.000 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0239 _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^)+(0.0072P)^2^+1.4757P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.0501 _reflns_Friedel_coverage 0.716 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 0.994 _reflns_number_gt 2054 _reflns_number_total 3161 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc05586j2.cif _cod_data_source_block K5 _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_database_code 1556536 _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 0.460 _shelx_estimated_absorpt_t_min 0.285 _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,H,H,H) groups 2. Shared sites {C8B, N2} {C8, N2B} 3. Uiso/Uaniso restraints and constraints Uanis(C8B) = Uanis(N2) Uanis(C8) = Uanis(N2B) 4. Others Sof(N2B)=Sof(H4B)=Sof(H7B)=Sof(H9BD)=Sof(H9BE)=Sof(H9BF)=Sof(H10D)=Sof(H10E)= Sof(H10F)=Sof(C8B)=1-FVAR(1) Sof(N2)=Sof(H4A)=Sof(H7A)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=Sof(H10A)=Sof(H10B)= Sof(H10C)=Sof(C8)=FVAR(1) 5.a Aromatic/amide H refined with riding coordinates: C4(H4A), C4(H4B), C7(H7A), C7(H7B), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15) 5.b Idealised Me refined as rotating group: C9(H9AA,H9AB,H9AC), C9(H9BD,H9BE,H9BF), C10(H10A,H10B,H10C), C10(H10D,H10E, H10F) ; _shelx_res_file ; TITL CM26K in P2(1)2(1)2(1) cm26k.res created by SHELXL-2018/3 at 13:08:12 on 04-Jun-2018 REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.160, Rweak 0.002, Alpha 0.035, Orientation as input REM Flack x = 0.274 ( 0.022 ) from Parsons' quotients REM Formula found by SHELXT: C23 N3 O3 Re CELL 0.71073 6.345 14.5492 16.7909 90 90 90 ZERR 4 0.0002 0.0005 0.0007 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N O Re UNIT 60 52 8 20 4 EADP C8B N2 EADP C8 N2B EXYZ C8B N2 EXYZ C8 N2B L.S. 10 PLAN 20 SIZE 0.213 0.145 0.117 TEMP -173.15 BOND $H fmap 2 ACTA 50 REM REM REM WGHT 0.007200 1.475700 FVAR 0.33439 0.63514 RE1 5 0.501835 -0.000287 0.339153 11.00000 0.01535 0.01550 = 0.01866 -0.00242 0.00038 -0.00149 O1 4 0.674911 -0.108912 0.482411 11.00000 0.04224 0.02614 = 0.02221 -0.00088 -0.00456 0.00127 O2 4 0.121602 -0.129185 0.350514 11.00000 0.02481 0.02678 = 0.05959 -0.00178 0.00382 -0.01072 O3 4 0.713871 -0.139378 0.227374 11.00000 0.02964 0.02810 = 0.02412 -0.00605 0.00304 0.00630 O4 4 0.366387 0.109347 0.405163 11.00000 0.01945 0.01378 = 0.01703 -0.00312 0.00451 -0.00140 O5 4 0.740892 0.102951 0.332551 11.00000 0.01216 0.01805 = 0.02329 -0.00344 0.00207 -0.00297 N1 3 0.376740 0.084278 0.239803 11.00000 0.01882 0.01057 = 0.02243 -0.00851 -0.00229 -0.00009 PART 1 N2 3 0.546594 0.342763 0.435475 21.00000 0.02078 0.01513 = 0.01518 0.00074 -0.00296 0.00073 PART 0 PART 2 N2B 3 0.734264 0.340553 0.398587 -21.00000 0.02877 0.01178 = 0.01185 0.00616 -0.00498 -0.00073 PART 0 C1 1 0.613067 -0.066509 0.428675 11.00000 0.02389 0.02000 = 0.02460 -0.01263 0.00960 -0.00181 C2 1 0.262905 -0.080302 0.345002 11.00000 0.03330 0.01402 = 0.02984 -0.00031 0.00070 0.00351 C3 1 0.632870 -0.087264 0.271627 11.00000 0.01180 0.02618 = 0.02372 0.00154 -0.00206 -0.00950 C4 1 0.419688 0.266067 0.438069 11.00000 0.01966 0.01646 = 0.01458 0.00433 -0.00056 0.00147 PART 1 AFIX 43 H4A 2 0.287789 0.269284 0.464697 21.00000 -1.20000 AFIX 43 PART 0 PART 2 H4B 2 0.287789 0.269284 0.464697 -21.00000 -1.20000 AFIX 0 PART 0 C5 1 0.480410 0.184492 0.402696 11.00000 0.01557 0.01477 = 0.01267 -0.00268 -0.00191 -0.00355 C6 1 0.681206 0.180991 0.363909 11.00000 0.01106 0.03017 = 0.00847 -0.00133 0.00038 0.00310 C7 1 0.801822 0.259942 0.362830 11.00000 0.01402 0.01404 = 0.02119 0.00273 0.00111 -0.00142 PART 1 AFIX 43 H7A 2 0.934817 0.258980 0.336855 21.00000 -1.20000 AFIX 43 PART 0 PART 2 H7B 2 0.934817 0.258980 0.336855 -21.00000 -1.20000 AFIX 0 PART 0 C9 1 0.873121 0.423549 0.399365 11.00000 0.02563 0.01046 = 0.02439 0.00138 0.00212 -0.00457 PART 1 AFIX 137 H9AA 2 0.800028 0.474923 0.373635 21.00000 -1.50000 H9AB 2 1.003708 0.410153 0.370441 21.00000 -1.50000 H9AC 2 0.906658 0.439984 0.454529 21.00000 -1.50000 AFIX 137 PART 0 PART 2 H9BD 2 0.934728 0.431078 0.452487 -21.00000 -1.50000 H9BE 2 0.789620 0.478080 0.386015 -21.00000 -1.50000 H9BF 2 0.986048 0.415901 0.360102 -21.00000 -1.50000 AFIX 0 PART 0 C10 1 0.471168 0.427758 0.475524 11.00000 0.01511 0.01988 = 0.01979 0.00063 0.00076 0.00097 PART 1 AFIX 137 H10A 2 0.581639 0.451197 0.510898 21.00000 -1.50000 H10B 2 0.344697 0.413799 0.506768 21.00000 -1.50000 H10C 2 0.437451 0.474302 0.435305 21.00000 -1.50000 AFIX 137 PART 0 PART 2 H10D 2 0.316762 0.427796 0.476952 -21.00000 -1.50000 H10E 2 0.520826 0.481668 0.445990 -21.00000 -1.50000 H10F 2 0.526200 0.429834 0.530029 -21.00000 -1.50000 AFIX 0 PART 0 C11 1 0.174600 0.114060 0.241546 11.00000 0.01690 0.01489 = 0.03178 -0.00808 -0.00035 -0.00725 AFIX 43 H11 2 0.085368 0.095184 0.283932 11.00000 -1.20000 AFIX 0 C12 1 0.095311 0.171066 0.183324 11.00000 0.02058 0.01289 = 0.03266 -0.00136 -0.00369 -0.00129 AFIX 43 H12 2 -0.046259 0.192039 0.186314 11.00000 -1.20000 AFIX 0 C13 1 0.221232 0.197471 0.121036 11.00000 0.02209 0.01893 = 0.03561 0.00546 -0.00841 -0.00459 AFIX 43 H13 2 0.167593 0.235403 0.079685 11.00000 -1.20000 AFIX 0 C14 1 0.427860 0.167651 0.119795 11.00000 0.03584 0.02605 = 0.01606 0.00106 0.00879 -0.01002 AFIX 43 H14 2 0.519784 0.185692 0.077961 11.00000 -1.20000 AFIX 0 C15 1 0.497788 0.112133 0.179273 11.00000 0.01436 0.02822 = 0.02274 -0.00941 0.00897 -0.00478 AFIX 43 H15 2 0.640204 0.092059 0.177759 11.00000 -1.20000 AFIX 0 PART 1 C8 1 0.734264 0.340553 0.398587 21.00000 0.02877 0.01178 = 0.01185 0.00616 -0.00498 -0.00073 PART 0 PART 2 C8B 1 0.546594 0.342763 0.435475 -21.00000 0.02078 0.01513 = 0.01518 0.00074 -0.00296 0.00073 HKLF 4 REM CM26K in P2(1)2(1)2(1) REM wR2 = 0.0501, GooF = S = 1.000, Restrained GooF = 1.000 for all data REM R1 = 0.0239 for 2054 Fo > 4sig(Fo) and 0.0517 for all 3161 data REM 211 parameters refined using 0 restraints END WGHT 0.0072 1.4757 REM Highest difference peak 0.494, deepest hole -0.533, 1-sigma level 0.121 Q1 1 -0.0106 0.0380 0.3643 11.00000 0.05 0.49 Q2 1 0.5918 -0.0563 0.3415 11.00000 0.05 0.43 Q3 1 0.4972 0.3817 0.4531 11.00000 0.05 0.40 Q4 1 0.3461 0.0000 0.3795 11.00000 0.05 0.40 Q5 1 0.4939 0.3005 0.4175 11.00000 0.05 0.40 Q6 1 0.8886 -0.1712 0.1808 11.00000 0.05 0.39 Q7 1 0.4214 -0.0699 0.3572 11.00000 0.05 0.39 Q8 1 0.8364 -0.1049 0.4982 11.00000 0.05 0.39 Q9 1 0.3102 0.4993 0.4091 11.00000 0.05 0.39 Q10 1 0.6133 0.0429 0.3191 11.00000 0.05 0.39 Q11 1 0.3517 -0.0362 0.2800 11.00000 0.05 0.39 Q12 1 1.0475 0.4931 0.3246 11.00000 0.05 0.38 Q13 1 0.6041 0.1242 0.1949 11.00000 0.05 0.38 Q14 1 1.0899 0.3389 0.4010 11.00000 0.05 0.38 Q15 1 0.1502 0.1009 0.1978 11.00000 0.05 0.37 Q16 1 -0.1323 0.1518 0.2351 11.00000 0.05 0.37 Q17 1 0.6437 0.4987 0.5347 11.00000 0.05 0.36 Q18 1 0.7328 -0.0989 0.2981 11.00000 0.05 0.36 Q19 1 0.8592 0.5575 0.4156 11.00000 0.05 0.36 Q20 1 0.3716 0.2338 -0.0239 11.00000 0.05 0.36 ; _shelx_res_checksum 16665 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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 0.50183(6) -0.00029(3) 0.33915(2) 0.01650(9) Uani 1 1 d . . . . O1 O 0.6749(11) -0.1089(4) 0.4824(4) 0.0302(17) Uani 1 1 d . . . . O2 O 0.1216(10) -0.1292(4) 0.3505(4) 0.0371(19) Uani 1 1 d . . . . O3 O 0.7139(10) -0.1394(4) 0.2274(4) 0.0273(16) Uani 1 1 d . . . . O4 O 0.3664(9) 0.1093(4) 0.4052(3) 0.0168(14) Uani 1 1 d . . . . O5 O 0.7409(9) 0.1030(4) 0.3326(3) 0.0178(15) Uani 1 1 d . . . . N1 N 0.3767(12) 0.0843(5) 0.2398(4) 0.0173(18) Uani 1 1 d . . . . N2 N 0.5466(12) 0.3428(5) 0.4355(5) 0.017(3) Uani 0.64(8) 1 d . P A 1 N2B N 0.7343(14) 0.3406(6) 0.3986(5) 0.017(3) Uani 0.36(8) 1 d . P A 2 C1 C 0.6131(15) -0.0665(6) 0.4287(6) 0.023(2) Uani 1 1 d . . . . C2 C 0.2629(16) -0.0803(6) 0.3450(6) 0.026(2) Uani 1 1 d . . . . C3 C 0.6329(14) -0.0873(6) 0.2716(6) 0.021(2) Uani 1 1 d . . . . C4 C 0.4197(14) 0.2661(6) 0.4381(5) 0.017(2) Uani 1 1 d . . . . H4A H 0.287789 0.269284 0.464697 0.020 Uiso 0.64(8) 1 calc R P A 1 H4B H 0.287789 0.269284 0.464697 0.020 Uiso 0.36(8) 1 calc R P A 2 C5 C 0.4804(16) 0.1845(5) 0.4027(4) 0.0143(18) Uani 1 1 d . . . . C6 C 0.6812(13) 0.1810(6) 0.3639(5) 0.017(2) Uani 1 1 d . . . . C7 C 0.8018(14) 0.2599(6) 0.3628(5) 0.016(2) Uani 1 1 d . . . . H7A H 0.934817 0.258980 0.336855 0.020 Uiso 0.64(8) 1 calc R P A 1 H7B H 0.934817 0.258980 0.336855 0.020 Uiso 0.36(8) 1 calc R P A 2 C9 C 0.8731(14) 0.4235(5) 0.3994(5) 0.020(2) Uani 1 1 d . . . . H9AA H 0.800028 0.474923 0.373635 0.030 Uiso 0.64(8) 1 calc GR P A 1 H9AB H 1.003708 0.410153 0.370441 0.030 Uiso 0.64(8) 1 calc GR P A 1 H9AC H 0.906658 0.439984 0.454529 0.030 Uiso 0.64(8) 1 calc GR P A 1 H9BD H 0.934728 0.431078 0.452487 0.030 Uiso 0.36(8) 1 calc GR P A 2 H9BE H 0.789620 0.478080 0.386015 0.030 Uiso 0.36(8) 1 calc GR P A 2 H9BF H 0.986048 0.415901 0.360102 0.030 Uiso 0.36(8) 1 calc GR P A 2 C10 C 0.4712(15) 0.4278(5) 0.4755(5) 0.018(2) Uani 1 1 d . . . . H10A H 0.581639 0.451197 0.510898 0.027 Uiso 0.64(8) 1 calc GR P A 1 H10B H 0.344697 0.413799 0.506768 0.027 Uiso 0.64(8) 1 calc GR P A 1 H10C H 0.437451 0.474302 0.435305 0.027 Uiso 0.64(8) 1 calc GR P A 1 H10D H 0.316762 0.427796 0.476952 0.027 Uiso 0.36(8) 1 calc GR P A 2 H10E H 0.520826 0.481668 0.445990 0.027 Uiso 0.36(8) 1 calc GR P A 2 H10F H 0.526200 0.429834 0.530029 0.027 Uiso 0.36(8) 1 calc GR P A 2 C11 C 0.1746(14) 0.1141(6) 0.2415(6) 0.021(2) Uani 1 1 d . . . . H11 H 0.085368 0.095184 0.283932 0.025 Uiso 1 1 calc R . . . C12 C 0.0953(14) 0.1711(6) 0.1833(5) 0.022(2) Uani 1 1 d . . . . H12 H -0.046259 0.192039 0.186314 0.026 Uiso 1 1 calc R . . . C13 C 0.2212(15) 0.1975(6) 0.1210(7) 0.026(3) Uani 1 1 d . . . . H13 H 0.167593 0.235403 0.079685 0.031 Uiso 1 1 calc R . . . C14 C 0.4279(15) 0.1677(6) 0.1198(6) 0.026(2) Uani 1 1 d . . . . H14 H 0.519784 0.185692 0.077961 0.031 Uiso 1 1 calc R . . . C15 C 0.4978(18) 0.1121(5) 0.1793(4) 0.0218(18) Uani 1 1 d . . . . H15 H 0.640204 0.092059 0.177759 0.026 Uiso 1 1 calc R . . . C8 C 0.7343(14) 0.3406(6) 0.3986(5) 0.017(3) Uani 0.64(8) 1 d . P A 1 C8B C 0.5466(12) 0.3428(5) 0.4355(5) 0.017(3) Uani 0.36(8) 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 0.01535(13) 0.01550(16) 0.01866(14) -0.00242(19) 0.0004(2) -0.0015(3) O1 0.042(4) 0.026(4) 0.022(4) -0.001(3) -0.005(3) 0.001(3) O2 0.025(4) 0.027(5) 0.060(6) -0.002(4) 0.004(4) -0.011(3) O3 0.030(4) 0.028(4) 0.024(4) -0.006(3) 0.003(3) 0.006(3) O4 0.019(3) 0.014(3) 0.017(4) -0.003(3) 0.005(3) -0.001(3) O5 0.012(3) 0.018(4) 0.023(4) -0.003(3) 0.002(3) -0.003(3) N1 0.019(4) 0.011(4) 0.022(5) -0.009(3) -0.002(4) 0.000(3) N2 0.021(6) 0.015(5) 0.015(4) 0.001(3) -0.003(3) 0.001(3) N2B 0.029(6) 0.012(5) 0.012(5) 0.006(4) -0.005(4) -0.001(4) C1 0.024(6) 0.020(6) 0.025(6) -0.013(5) 0.010(5) -0.002(4) C2 0.033(6) 0.014(5) 0.030(6) 0.000(5) 0.001(5) 0.004(5) C3 0.012(5) 0.026(6) 0.024(6) 0.002(5) -0.002(4) -0.010(4) C4 0.020(5) 0.016(5) 0.015(5) 0.004(4) -0.001(4) 0.001(4) C5 0.016(5) 0.015(4) 0.013(4) -0.003(3) -0.002(5) -0.004(5) C6 0.011(5) 0.030(6) 0.008(5) -0.001(4) 0.000(4) 0.003(4) C7 0.014(5) 0.014(5) 0.021(6) 0.003(4) 0.001(4) -0.001(4) C9 0.026(5) 0.010(5) 0.024(6) 0.001(4) 0.002(4) -0.005(4) C10 0.015(6) 0.020(5) 0.020(4) 0.001(4) 0.001(4) 0.001(4) C11 0.017(5) 0.015(5) 0.032(6) -0.008(4) 0.000(4) -0.007(4) C12 0.021(5) 0.013(5) 0.033(6) -0.001(4) -0.004(4) -0.001(4) C13 0.022(6) 0.019(6) 0.036(7) 0.005(5) -0.008(5) -0.005(5) C14 0.036(7) 0.026(6) 0.016(6) 0.001(4) 0.009(4) -0.010(4) C15 0.014(4) 0.028(5) 0.023(5) -0.009(3) 0.009(6) -0.005(6) C8 0.029(6) 0.012(5) 0.012(5) 0.006(4) -0.005(4) -0.001(4) C8B 0.021(6) 0.015(5) 0.015(4) 0.001(3) -0.003(3) 0.001(3) 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 O5 77.7(2) O4 Re1 N1 80.3(2) O5 Re1 N1 79.9(2) C1 Re1 O4 96.7(3) C1 Re1 O5 97.6(3) C1 Re1 N1 176.4(3) C2 Re1 O4 96.3(3) C2 Re1 O5 172.8(3) C2 Re1 N1 95.3(3) C2 Re1 C1 86.9(4) C3 Re1 O4 173.2(3) C3 Re1 O5 97.3(3) C3 Re1 N1 94.4(4) C3 Re1 C1 88.4(4) C3 Re1 C2 88.4(4) C5 O4 Re1 112.7(5) C6 O5 Re1 112.6(5) C11 N1 Re1 120.0(6) C15 N1 Re1 122.3(7) C15 N1 C11 117.6(8) C4 N2 C10 118.1(7) C8 N2 C4 120.9(8) C8 N2 C10 120.9(8) C7 N2B C9 120.3(8) C8B N2B C7 119.6(8) C8B N2B C9 120.0(8) O1 C1 Re1 177.6(8) O2 C2 Re1 178.1(9) O3 C3 Re1 177.7(9) N2 C4 H4A 119.4 N2 C4 C5 121.3(8) C5 C4 H4A 119.4 C5 C4 H4B 119.4 C8B C4 H4B 119.4 C8B C4 C5 121.3(8) O4 C5 C4 123.3(9) O4 C5 C6 118.4(7) C4 C5 C6 118.3(8) O5 C6 C5 118.1(8) O5 C6 C7 123.8(8) C7 C6 C5 118.0(8) N2B C7 H7B 119.1 C6 C7 N2B 121.8(9) C6 C7 H7A 119.1 C6 C7 H7B 119.1 C6 C7 C8 121.8(9) C8 C7 H7A 119.1 N2B C9 H9BD 109.5 N2B C9 H9BE 109.5 N2B C9 H9BF 109.5 H9AA C9 H9AB 109.5 H9AA C9 H9AC 109.5 H9AB C9 H9AC 109.5 H9BD C9 H9BE 109.5 H9BD C9 H9BF 109.5 H9BE C9 H9BF 109.5 C8 C9 H9AA 109.5 C8 C9 H9AB 109.5 C8 C9 H9AC 109.5 N2 C10 H10A 109.5 N2 C10 H10B 109.5 N2 C10 H10C 109.5 H10A C10 H10B 109.5 H10A C10 H10C 109.5 H10B C10 H10C 109.5 H10D C10 H10E 109.5 H10D C10 H10F 109.5 H10E C10 H10F 109.5 C8B C10 H10D 109.5 C8B C10 H10E 109.5 C8B C10 H10F 109.5 N1 C11 H11 119.2 N1 C11 C12 121.6(9) C12 C11 H11 119.2 C11 C12 H12 120.1 C13 C12 C11 119.8(9) C13 C12 H12 120.1 C12 C13 H13 120.8 C12 C13 C14 118.5(10) C14 C13 H13 120.8 C13 C14 H14 120.5 C15 C14 C13 119.0(10) C15 C14 H14 120.5 N1 C15 C14 123.5(10) N1 C15 H15 118.3 C14 C15 H15 118.3 N2 C8 C7 119.6(8) N2 C8 C9 120.0(8) C7 C8 C9 120.3(8) N2B C8B C4 120.9(8) N2B C8B C10 120.9(8) C4 C8B C10 118.1(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Re1 O4 2.124(5) Re1 O5 2.138(6) Re1 N1 2.220(7) Re1 C1 1.920(10) Re1 C2 1.914(10) Re1 C3 1.892(10) O1 C1 1.161(10) O2 C2 1.148(11) O3 C3 1.179(10) O4 C5 1.312(9) O5 C6 1.308(10) N1 C11 1.354(11) N1 C15 1.337(10) N2 C4 1.377(11) N2 C10 1.487(10) N2 C8 1.343(10) N2B C7 1.386(12) N2B C9 1.495(11) N2B C8B 1.343(10) C4 H4A 0.9500 C4 H4B 0.9500 C4 C5 1.382(11) C4 C8B 1.377(11) C5 C6 1.432(12) C6 C7 1.380(12) C7 H7A 0.9500 C7 H7B 0.9500 C7 C8 1.386(12) C9 H9AA 0.9800 C9 H9AB 0.9800 C9 H9AC 0.9800 C9 H9BD 0.9800 C9 H9BE 0.9800 C9 H9BF 0.9800 C9 C8 1.495(11) C10 H10A 0.9800 C10 H10B 0.9800 C10 H10C 0.9800 C10 H10D 0.9800 C10 H10E 0.9800 C10 H10F 0.9800 C10 C8B 1.487(10) C11 H11 0.9500 C11 C12 1.377(12) C12 H12 0.9500 C12 C13 1.371(13) C13 H13 0.9500 C13 C14 1.381(12) C14 H14 0.9500 C14 C15 1.359(12) C15 H15 0.9500