#------------------------------------------------------------------------------ #$Date: 2020-04-23 04:01:23 +0300 (Thu, 23 Apr 2020) $ #$Revision: 251070 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157477.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_7157477 loop_ _publ_author_name 'Sharma, Charu' 'Srivastava, Avinash Kumar' 'Sharma, Kamal Nayan' 'Joshi, Raj Kumar' _publ_section_title ; Half-Sandwich (\h5-Cp*)Rh(III) Complex of Pyrazolated Organo-Sulfur/Selenium/Tellurium Ligands: Efficient Catalysts for Base/ Solvent Free C−N Coupling of Chloroarenes under Aerobic Conditions ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D0OB00538J _journal_year 2020 _chemical_formula_moiety 'C21 H26 Br Cl N2 Rh S, F6 P' _chemical_formula_sum 'C21 H26 Br Cl F6 N2 P Rh S' _chemical_formula_weight 701.73 _space_group_crystal_system monoclinic _space_group_IT_number 9 _space_group_name_Hall 'C -2yc' _space_group_name_H-M_alt 'C 1 c 1' _atom_sites_solution_hydrogens geom _audit_creation_date 2020-02-02 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-02-02 deposited with the CCDC. 2020-04-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.874(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.562(3) _cell_length_b 11.151(2) _cell_length_c 19.041(4) _cell_measurement_reflns_used 5351 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 23.67 _cell_measurement_theta_min 2.25 _cell_volume 2665.8(10) _computing_cell_refinement 'SAINT v6.28A (Bruker, 2002)' _computing_data_reduction 'SAINT v6.28A (Bruker, 2002)' _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 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_unetI/netI 0.0579 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 11514 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 24.998 _diffrn_reflns_theta_max 24.998 _diffrn_reflns_theta_min 2.140 _exptl_absorpt_coefficient_mu 2.433 _exptl_absorpt_correction_T_max 0.600 _exptl_absorpt_correction_T_min 0.550 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.748 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1392 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: acetonitrile and methanol' _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.230 _exptl_crystal_size_min 0.210 _refine_diff_density_max 0.758 _refine_diff_density_min -1.007 _refine_diff_density_rms 0.101 _refine_ls_abs_structure_details ; Flack x determined using 1770 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.025(7) _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 312 _refine_ls_number_reflns 4650 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.068 _refine_ls_R_factor_all 0.0544 _refine_ls_R_factor_gt 0.0477 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0457P)^2^+4.5968P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1033 _refine_ls_wR_factor_ref 0.1057 _reflns_Friedel_coverage 0.991 _reflns_Friedel_fraction_full 0.993 _reflns_Friedel_fraction_max 0.993 _reflns_number_gt 4142 _reflns_number_total 4650 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL kns6 in Cc kns6m.res created by SHELXL-2017/1 at 13:45:45 on 02-Feb-2020 CELL 0.71073 12.5625 11.1514 19.0413 90 91.874 90 ZERR 14 0.0025 0.0022 0.0037 0 0.003 0 LATT -7 SYMM +X,-Y,0.5+Z SFAC C H N F P S Cl Br Rh UNIT 14 14 14 14 14 14 14 14 14 L.S. 4 PLAN 2 TEMP 0 FREE C15 C13 FREE F1 F2 FREE N2 C11 BOND $H CONF HTAB fmap 2 acta OMIT -1 50 REM REM REM WGHT 0.045700 4.596800 FVAR 0.06631 BR1 8 0.848996 0.929143 0.166757 11.00000 0.10366 0.06155 = 0.09446 -0.04060 0.00462 -0.00301 C1 1 0.958586 0.318047 -0.166218 11.00000 0.07212 0.05018 = 0.06215 -0.00325 0.01332 -0.00498 AFIX 43 H1 2 0.900050 0.266954 -0.166920 11.00000 -1.20000 AFIX 0 C2 1 1.044563 0.290645 -0.205496 11.00000 0.08347 0.07654 = 0.08271 -0.02727 0.02523 0.00968 AFIX 43 H2 2 1.046288 0.219093 -0.230523 11.00000 -1.20000 AFIX 0 C3 1 1.126182 0.367604 -0.207631 11.00000 0.07696 0.14326 = 0.06557 -0.00283 0.02620 0.02409 AFIX 43 H3 2 1.183015 0.351186 -0.236214 11.00000 -1.20000 AFIX 0 C4 1 1.126827 0.470374 -0.168108 11.00000 0.06391 0.12890 = 0.07083 0.00597 0.01728 -0.03509 AFIX 43 H4 2 1.184848 0.522007 -0.169564 11.00000 -1.20000 AFIX 0 C5 1 1.044317 0.497964 -0.126953 11.00000 0.05770 0.06319 = 0.05761 -0.00346 0.01489 -0.02052 AFIX 43 H5 2 1.045192 0.567455 -0.099937 11.00000 -1.20000 AFIX 0 C6 1 0.957577 0.418870 -0.126214 11.00000 0.06497 0.04787 = 0.03092 -0.00399 0.00390 -0.00017 C7 1 0.810337 0.600471 -0.097945 11.00000 0.10098 0.04218 = 0.04370 0.00475 -0.00405 0.01956 AFIX 23 H7A 2 0.874185 0.649149 -0.093424 11.00000 -1.20000 H7B 2 0.783832 0.605357 -0.146281 11.00000 -1.20000 AFIX 0 C8 1 0.728613 0.647767 -0.050595 11.00000 0.06676 0.05780 = 0.05180 -0.00949 -0.02531 0.01645 AFIX 23 H8A 2 0.690108 0.712686 -0.073896 11.00000 -1.20000 H8B 2 0.677993 0.584800 -0.040684 11.00000 -1.20000 AFIX 0 C9 1 0.771334 0.804092 0.041531 11.00000 0.04426 0.02638 = 0.06093 -0.00636 0.00169 0.01621 AFIX 43 H9 2 0.737106 0.869741 0.020844 11.00000 -1.20000 AFIX 0 C10 1 0.826317 0.800930 0.104625 11.00000 0.05621 0.04107 = 0.05675 -0.02552 0.01027 -0.00353 C11 1 0.863072 0.687491 0.111767 11.00000 0.06633 0.05192 = 0.05438 -0.00737 -0.01369 0.00126 AFIX 43 H11 2 0.904913 0.660958 0.149856 11.00000 -1.20000 AFIX 0 C12 1 0.735182 0.331863 0.080863 11.00000 0.03993 0.03806 = 0.07590 0.02365 0.01887 -0.01390 C13 1 0.783715 0.381559 0.138521 11.00000 0.10239 0.06280 = 0.04738 0.00083 0.02807 -0.03628 C14 1 0.885051 0.342777 0.145157 11.00000 0.11302 0.09066 = 0.08200 0.07645 -0.01534 -0.03795 C15 1 0.905155 0.261302 0.086642 11.00000 0.04418 0.05642 = 0.18854 0.07794 0.05106 0.02147 C16 1 0.805555 0.255173 0.046701 11.00000 0.05781 0.02002 = 0.07906 0.00809 0.02570 -0.01424 C17 1 0.619356 0.344795 0.060026 11.00000 0.05071 0.07875 = 0.22924 0.05525 0.01578 -0.01556 AFIX 137 H17A 2 0.579532 0.281337 0.080872 11.00000 -1.50000 H17B 2 0.610874 0.340566 0.009799 11.00000 -1.50000 H17C 2 0.593661 0.420745 0.076095 11.00000 -1.50000 AFIX 0 C18 1 0.733245 0.463548 0.191324 11.00000 0.23197 0.08846 = 0.13319 -0.02408 0.11563 -0.04547 AFIX 137 H18A 2 0.728325 0.543235 0.172419 11.00000 -1.50000 H18B 2 0.776171 0.464600 0.233966 11.00000 -1.50000 H18C 2 0.663224 0.434816 0.201079 11.00000 -1.50000 AFIX 0 C19 1 0.978271 0.361393 0.197472 11.00000 0.22504 0.28658 = 0.18490 0.18154 -0.14964 -0.16786 AFIX 137 H19A 2 1.030570 0.299934 0.191046 11.00000 -1.50000 H19B 2 0.953120 0.357414 0.244484 11.00000 -1.50000 H19C 2 1.009743 0.438538 0.189786 11.00000 -1.50000 AFIX 0 C20 1 1.001351 0.186356 0.072667 11.00000 0.06812 0.07270 = 0.52272 0.11526 0.08945 0.03336 AFIX 137 H20A 2 0.995044 0.153574 0.026098 11.00000 -1.50000 H20B 2 1.006447 0.122236 0.106250 11.00000 -1.50000 H20C 2 1.064119 0.235299 0.076710 11.00000 -1.50000 AFIX 0 C21 1 0.776209 0.178325 -0.015376 11.00000 0.22884 0.08546 = 0.09827 -0.04167 0.07862 -0.09287 AFIX 137 H21A 2 0.735503 0.224686 -0.049181 11.00000 -1.50000 H21B 2 0.734500 0.111448 -0.000420 11.00000 -1.50000 H21C 2 0.839797 0.149539 -0.036354 11.00000 -1.50000 AFIX 0 CL1 7 1.050549 0.500737 0.047886 11.00000 0.04003 0.05427 = 0.07066 0.00781 0.00062 -0.00719 F1 4 0.898816 0.851096 0.797309 11.00000 0.15781 0.14397 = 0.19677 -0.06945 -0.06968 0.04512 F2 4 1.038274 0.955960 0.791373 11.00000 0.20487 0.18281 = 0.28219 0.12861 0.16069 0.08493 F3 4 0.900555 1.035505 0.839688 11.00000 0.13064 0.06934 = 0.11652 -0.00005 0.02237 0.01356 F4 4 1.039532 0.987498 0.902080 11.00000 0.24057 0.13376 = 0.30465 -0.05450 -0.16133 -0.02413 F5 4 0.895445 0.879986 0.906552 11.00000 0.25031 0.13929 = 0.18072 0.06426 0.11019 0.01609 F6 4 1.040104 0.801941 0.860444 11.00000 0.13970 0.08076 = 0.18806 0.02715 -0.04459 0.03248 N1 3 0.833108 0.619928 0.059215 11.00000 0.03014 0.03978 = 0.04541 0.00776 -0.00465 0.00086 N2 3 0.777247 0.691632 0.015585 11.00000 0.05755 0.03597 = 0.04486 0.00116 0.01945 0.01203 P1 5 0.972944 0.918935 0.850809 11.00000 0.07947 0.04415 = 0.06552 0.00190 -0.00540 -0.01132 RH1 9 0.869870 0.435056 0.047260 11.00000 0.03714 0.02682 = 0.03780 0.00477 0.00437 -0.00436 S1 6 0.842288 0.447732 -0.076847 11.00000 0.05116 0.03457 = 0.04413 -0.00543 0.00413 -0.00727 HKLF 4 REM kns6 in Cc REM R1 = 0.0477 for 4142 Fo > 4sig(Fo) and 0.0544 for all 4650 data REM 312 parameters refined using 2 restraints END WGHT 0.0455 4.6292 REM Instructions for potential hydrogen bonds EQIV $1 x, y-1, z-1 HTAB C1 F3_$1 EQIV $2 x, y, z-1 HTAB C7 F5_$2 EQIV $3 x-1/2, y-1/2, z-1 HTAB C8 F4_$3 EQIV $4 x-1/2, y+1/2, z HTAB C9 Cl1_$4 REM Highest difference peak 0.758, deepest hole -1.007, 1-sigma level 0.101 Q1 1 0.8021 0.3853 0.0389 11.00000 0.05 0.76 Q2 1 0.8670 0.4073 0.0998 11.00000 0.05 0.73 REM The information below was added by Olex2. REM REM R1 = 0.0477 for 4142 Fo > 4sig(Fo) and 0.0544 for all 14544 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.76, deepest hole -1.01 REM Mean Shift 0.001, Max Shift 0.028. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0544 REM R1_gt = 0.0477 REM wR_ref = 0.1057 REM GOOF = 1.068 REM Shift_max = 0.028 REM Shift_mean = 0.001 REM Reflections_all = 14544 REM Reflections_gt = 4142 REM Parameters = n/a REM Hole = -1.01 REM Peak = 0.76 REM Flack = 0.025(7) ; _cod_data_source_file d0ob00538j2.cif _cod_data_source_block Complex1_CCDC1 _cod_original_cell_volume 2666.1(9) _cod_database_code 7157477 _shelx_shelxl_version_number 2017/1 _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 0.108 _shelx_estimated_absorpt_t_min 0.180 _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.a Secondary CH2 refined with riding coordinates: C7(H7A,H7B), C8(H8A,H8B) 2.b Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C11(H11) 2.c Idealised Me refined as rotating group: C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B, H20C), C21(H21A,H21B,H21C) ; _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, 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 _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.84900(14) 0.92914(14) 0.16676(9) 0.0865(6) Uani 1 1 d . . . . . C1 C 0.9586(11) 0.3180(12) -0.1662(7) 0.061(3) Uani 1 1 d . . . . . H1 H 0.900050 0.266954 -0.166920 0.073 Uiso 1 1 calc R . . . . C2 C 1.0446(13) 0.2906(14) -0.2055(8) 0.080(4) Uani 1 1 d . . . . . H2 H 1.046288 0.219093 -0.230523 0.096 Uiso 1 1 calc R . . . . C3 C 1.1262(14) 0.368(2) -0.2076(8) 0.095(5) Uani 1 1 d . . . . . H3 H 1.183015 0.351186 -0.236214 0.114 Uiso 1 1 calc R . . . . C4 C 1.1268(12) 0.4704(17) -0.1681(8) 0.088(5) Uani 1 1 d . . . . . H4 H 1.184848 0.522007 -0.169564 0.105 Uiso 1 1 calc R . . . . C5 C 1.0443(10) 0.4980(12) -0.1270(7) 0.059(3) Uani 1 1 d . . . . . H5 H 1.045192 0.567455 -0.099937 0.071 Uiso 1 1 calc R . . . . C6 C 0.9576(10) 0.4189(10) -0.1262(6) 0.048(3) Uani 1 1 d . . . . . C7 C 0.8103(12) 0.6005(11) -0.0979(6) 0.062(4) Uani 1 1 d . . . . . H7A H 0.874185 0.649149 -0.093424 0.075 Uiso 1 1 calc R . . . . H7B H 0.783832 0.605357 -0.146281 0.075 Uiso 1 1 calc R . . . . C8 C 0.7286(10) 0.6478(12) -0.0506(6) 0.059(3) Uani 1 1 d . . . . . H8A H 0.690108 0.712686 -0.073896 0.071 Uiso 1 1 calc R . . . . H8B H 0.677993 0.584800 -0.040684 0.071 Uiso 1 1 calc R . . . . C9 C 0.7713(8) 0.8041(9) 0.0415(6) 0.044(2) Uani 1 1 d . . . . . H9 H 0.737106 0.869741 0.020844 0.053 Uiso 1 1 calc R . . . . C10 C 0.8263(10) 0.8009(10) 0.1046(6) 0.051(3) Uani 1 1 d . . . . . C11 C 0.8631(10) 0.6875(12) 0.1118(6) 0.058(3) Uani 1 1 d . . . . . H11 H 0.904913 0.660958 0.149856 0.069 Uiso 1 1 calc R . . . . C12 C 0.7352(8) 0.3319(10) 0.0809(6) 0.051(3) Uani 1 1 d . . . . . C13 C 0.7837(14) 0.3816(13) 0.1385(7) 0.070(4) Uani 1 1 d . . . . . C14 C 0.8851(17) 0.3428(17) 0.1452(9) 0.096(6) Uani 1 1 d . . . . . C15 C 0.9052(11) 0.2613(14) 0.0866(12) 0.095(7) Uani 1 1 d . . . . . C16 C 0.8056(10) 0.2552(9) 0.0467(7) 0.052(3) Uani 1 1 d . . . . . C17 C 0.6194(12) 0.3448(16) 0.0600(12) 0.119(8) Uani 1 1 d . . . . . H17A H 0.579532 0.281337 0.080872 0.179 Uiso 1 1 calc GR . . . . H17B H 0.610874 0.340566 0.009799 0.179 Uiso 1 1 calc GR . . . . H17C H 0.593661 0.420745 0.076095 0.179 Uiso 1 1 calc GR . . . . C18 C 0.733(2) 0.4635(18) 0.1913(13) 0.149(11) Uani 1 1 d . . . . . H18A H 0.728325 0.543235 0.172419 0.223 Uiso 1 1 calc GR . . . . H18B H 0.776171 0.464600 0.233966 0.223 Uiso 1 1 calc GR . . . . H18C H 0.663224 0.434816 0.201079 0.223 Uiso 1 1 calc GR . . . . C19 C 0.978(3) 0.361(3) 0.1975(15) 0.24(2) Uani 1 1 d . . . . . H19A H 1.030570 0.299934 0.191046 0.353 Uiso 1 1 calc GR . . . . H19B H 0.953120 0.357414 0.244484 0.353 Uiso 1 1 calc GR . . . . H19C H 1.009743 0.438538 0.189786 0.353 Uiso 1 1 calc GR . . . . C20 C 1.0014(15) 0.1864(18) 0.073(2) 0.219(19) Uani 1 1 d . . . . . H20A H 0.995044 0.153574 0.026098 0.329 Uiso 1 1 calc GR . . . . H20B H 1.006447 0.122236 0.106250 0.329 Uiso 1 1 calc GR . . . . H20C H 1.064119 0.235299 0.076710 0.329 Uiso 1 1 calc GR . . . . C21 C 0.7762(19) 0.1783(15) -0.0154(9) 0.136(10) Uani 1 1 d . . . . . H21A H 0.735503 0.224686 -0.049181 0.204 Uiso 1 1 calc GR . . . . H21B H 0.734500 0.111448 -0.000420 0.204 Uiso 1 1 calc GR . . . . H21C H 0.839797 0.149539 -0.036354 0.204 Uiso 1 1 calc GR . . . . Cl1 Cl 1.0505(2) 0.5007(3) 0.04789(17) 0.0550(7) Uani 1 1 d . . . . . F1 F 0.8988(12) 0.8511(14) 0.7973(9) 0.168(6) Uani 1 1 d . . . . . F2 F 1.0383(15) 0.9560(15) 0.7914(12) 0.220(11) Uani 1 1 d . . . . . F3 F 0.9006(9) 1.0355(8) 0.8397(6) 0.105(3) Uani 1 1 d . . . . . F4 F 1.0395(17) 0.9875(15) 0.9021(13) 0.230(10) Uani 1 1 d . . . . . F5 F 0.8954(15) 0.8800(14) 0.9066(9) 0.188(7) Uani 1 1 d . . . . . F6 F 1.0401(10) 0.8019(10) 0.8604(7) 0.137(4) Uani 1 1 d . . . . . N1 N 0.8331(6) 0.6199(8) 0.0592(4) 0.039(2) Uani 1 1 d . . . . . N2 N 0.7772(7) 0.6916(8) 0.0156(4) 0.046(2) Uani 1 1 d . . . . . P1 P 0.9729(3) 0.9189(3) 0.85081(19) 0.0632(9) Uani 1 1 d . . . . . Rh1 Rh 0.86987(3) 0.43506(6) 0.04726(3) 0.0339(2) Uani 1 1 d . . . . . S1 S 0.8423(2) 0.4477(2) -0.07685(14) 0.0432(6) Uani 1 1 d . . . . . 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 Br1 0.1037(12) 0.0615(10) 0.0945(12) -0.0406(9) 0.0046(10) -0.0030(9) C1 0.072(8) 0.050(7) 0.062(8) -0.003(6) 0.013(6) -0.005(6) C2 0.083(10) 0.077(10) 0.083(10) -0.027(8) 0.025(8) 0.010(9) C3 0.077(11) 0.143(17) 0.066(10) -0.003(10) 0.026(8) 0.024(11) C4 0.064(9) 0.129(15) 0.071(10) 0.006(10) 0.017(7) -0.035(9) C5 0.058(7) 0.063(8) 0.058(7) -0.003(6) 0.015(6) -0.021(6) C6 0.065(7) 0.048(7) 0.031(5) -0.004(5) 0.004(5) 0.000(5) C7 0.101(10) 0.042(7) 0.044(7) 0.005(5) -0.004(7) 0.020(7) C8 0.067(8) 0.058(8) 0.052(7) -0.009(6) -0.025(6) 0.016(6) C9 0.044(6) 0.026(5) 0.061(7) -0.006(5) 0.002(5) 0.016(5) C10 0.056(7) 0.041(7) 0.057(7) -0.026(5) 0.010(6) -0.004(5) C11 0.066(8) 0.052(7) 0.054(7) -0.007(6) -0.014(6) 0.001(6) C12 0.040(6) 0.038(6) 0.076(8) 0.024(6) 0.019(6) -0.014(5) C13 0.102(12) 0.063(8) 0.047(8) 0.001(6) 0.028(8) -0.036(9) C14 0.113(14) 0.091(13) 0.082(12) 0.076(11) -0.015(10) -0.038(11) C15 0.044(8) 0.056(9) 0.19(2) 0.078(12) 0.051(10) 0.021(7) C16 0.058(8) 0.020(5) 0.079(8) 0.008(5) 0.026(6) -0.014(5) C17 0.051(8) 0.079(12) 0.23(2) 0.055(13) 0.016(11) -0.016(8) C18 0.23(3) 0.088(14) 0.133(19) -0.024(12) 0.12(2) -0.045(16) C19 0.23(3) 0.29(4) 0.18(3) 0.18(3) -0.15(2) -0.17(3) C20 0.068(12) 0.073(13) 0.52(6) 0.12(2) 0.09(2) 0.033(10) C21 0.23(3) 0.085(13) 0.098(13) -0.042(10) 0.079(15) -0.093(15) Cl1 0.0400(15) 0.0543(17) 0.0707(19) 0.0078(14) 0.0006(12) -0.0072(13) F1 0.158(12) 0.144(12) 0.197(14) -0.069(11) -0.070(11) 0.045(10) F2 0.205(16) 0.183(15) 0.28(2) 0.129(15) 0.161(17) 0.085(13) F3 0.131(8) 0.069(6) 0.117(8) 0.000(5) 0.022(6) 0.014(5) F4 0.241(19) 0.134(12) 0.30(3) -0.054(14) -0.161(18) -0.024(13) F5 0.250(18) 0.139(11) 0.181(14) 0.064(11) 0.110(13) 0.016(13) F6 0.140(10) 0.081(7) 0.188(12) 0.027(7) -0.045(8) 0.032(7) N1 0.030(4) 0.040(5) 0.045(5) 0.008(4) -0.005(4) 0.001(4) N2 0.058(6) 0.036(5) 0.045(5) 0.001(4) 0.019(4) 0.012(4) P1 0.079(2) 0.0441(18) 0.066(2) 0.0019(15) -0.0054(17) -0.0113(16) Rh1 0.0371(4) 0.0268(3) 0.0378(4) 0.0048(4) 0.0044(3) -0.0044(5) S1 0.0512(15) 0.0346(14) 0.0441(15) -0.0054(11) 0.0041(12) -0.0073(12) 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' Cl Cl 0.1484 0.1585 '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' Rh Rh -1.1178 0.9187 '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_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1 119.6 . . ? C6 C1 H1 119.6 . . ? C6 C1 C2 120.9(14) . . ? C1 C2 H2 120.2 . . ? C3 C2 C1 119.5(14) . . ? C3 C2 H2 120.2 . . ? C2 C3 H3 119.7 . . ? C2 C3 C4 120.7(13) . . ? C4 C3 H3 119.7 . . ? C3 C4 H4 119.5 . . ? C5 C4 C3 121.1(15) . . ? C5 C4 H4 119.5 . . ? C4 C5 H5 120.9 . . ? C4 C5 C6 118.2(13) . . ? C6 C5 H5 120.9 . . ? C1 C6 C5 119.6(12) . . ? C1 C6 S1 117.9(10) . . ? C5 C6 S1 122.5(9) . . ? H7A C7 H7B 108.1 . . ? C8 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? C8 C7 S1 110.8(9) . . ? S1 C7 H7A 109.5 . . ? S1 C7 H7B 109.5 . . ? C7 C8 H8A 109.4 . . ? C7 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? N2 C8 C7 111.3(10) . . ? N2 C8 H8A 109.4 . . ? N2 C8 H8B 109.4 . . ? C10 C9 H9 127.3 . . ? N2 C9 H9 127.3 . . ? N2 C9 C10 105.4(9) . . ? C9 C10 Br1 126.7(9) . . ? C11 C10 Br1 127.4(10) . . ? C11 C10 C9 105.9(10) . . ? C10 C11 H11 124.0 . . ? N1 C11 C10 112.1(11) . . ? N1 C11 H11 124.0 . . ? C13 C12 C16 110.5(12) . . ? C13 C12 C17 125.5(14) . . ? C13 C12 Rh1 71.7(7) . . ? C16 C12 C17 123.7(14) . . ? C16 C12 Rh1 71.1(5) . . ? C17 C12 Rh1 129.2(9) . . ? C12 C13 C18 126.7(19) . . ? C12 C13 Rh1 71.7(6) . . ? C14 C13 C12 110.1(14) . . ? C14 C13 C18 123(2) . . ? C14 C13 Rh1 70.6(7) . . ? C18 C13 Rh1 126.8(11) . . ? C13 C14 C15 108.3(15) . . ? C13 C14 C19 136(3) . . ? C13 C14 Rh1 72.9(8) . . ? C15 C14 C19 116(3) . . ? C15 C14 Rh1 69.4(8) . . ? C19 C14 Rh1 123.3(12) . . ? C14 C15 C20 130(2) . . ? C14 C15 Rh1 70.3(8) . . ? C16 C15 C14 105.2(13) . . ? C16 C15 C20 125(2) . . ? C16 C15 Rh1 71.9(7) . . ? C20 C15 Rh1 127.4(11) . . ? C12 C16 C15 105.9(13) . . ? C12 C16 C21 124.9(14) . . ? C12 C16 Rh1 71.0(6) . . ? C15 C16 C21 129.0(17) . . ? C15 C16 Rh1 68.7(7) . . ? C21 C16 Rh1 128.1(9) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20B 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C16 C21 H21A 109.5 . . ? C16 C21 H21B 109.5 . . ? C16 C21 H21C 109.5 . . ? H21A C21 H21B 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C11 N1 N2 105.4(9) . . ? C11 N1 Rh1 125.9(8) . . ? N2 N1 Rh1 128.7(7) . . ? C9 N2 C8 126.7(10) . . ? N1 N2 C8 122.0(9) . . ? N1 N2 C9 111.2(9) . . ? F1 P1 F3 89.0(7) . . ? F1 P1 F6 88.9(7) . . ? F2 P1 F1 88.3(13) . . ? F2 P1 F3 90.0(7) . . ? F2 P1 F5 173.9(14) . . ? F2 P1 F6 90.7(8) . . ? F4 P1 F1 177.4(10) . . ? F4 P1 F2 92.6(14) . . ? F4 P1 F3 88.5(9) . . ? F4 P1 F5 92.7(14) . . ? F4 P1 F6 93.6(9) . . ? F5 P1 F1 86.3(11) . . ? F5 P1 F3 87.2(7) . . ? F5 P1 F6 92.0(8) . . ? F6 P1 F3 177.8(7) . . ? C12 Rh1 C13 36.6(5) . . ? C12 Rh1 C16 37.9(4) . . ? C12 Rh1 Cl1 156.4(3) . . ? C12 Rh1 S1 103.6(3) . . ? C13 Rh1 C16 63.3(5) . . ? C13 Rh1 Cl1 125.6(5) . . ? C13 Rh1 S1 138.9(5) . . ? C14 Rh1 C12 62.1(6) . . ? C14 Rh1 C13 36.5(6) . . ? C14 Rh1 C16 65.1(6) . . ? C14 Rh1 Cl1 94.9(5) . . ? C14 Rh1 S1 154.4(6) . . ? C15 Rh1 C12 64.2(5) . . ? C15 Rh1 C13 64.4(6) . . ? C15 Rh1 C14 40.3(8) . . ? C15 Rh1 C16 39.4(6) . . ? C15 Rh1 Cl1 95.2(4) . . ? C15 Rh1 N1 153.1(7) . . ? C15 Rh1 S1 115.3(7) . . ? C16 Rh1 Cl1 129.8(3) . . ? C16 Rh1 S1 90.5(4) . . ? N1 Rh1 C12 108.0(4) . . ? N1 Rh1 C13 93.7(5) . . ? N1 Rh1 C14 112.8(7) . . ? N1 Rh1 C16 144.8(4) . . ? N1 Rh1 Cl1 84.9(2) . . ? N1 Rh1 S1 91.4(2) . . ? S1 Rh1 Cl1 95.41(10) . . ? C6 S1 C7 103.5(6) . . ? C6 S1 Rh1 114.7(4) . . ? C7 S1 Rh1 107.6(4) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C10 1.872(10) . ? C1 H1 0.9300 . ? C1 C2 1.368(19) . ? C1 C6 1.358(17) . ? C2 H2 0.9300 . ? C2 C3 1.34(2) . ? C3 H3 0.9300 . ? C3 C4 1.37(2) . ? C4 H4 0.9300 . ? C4 C5 1.355(19) . ? C5 H5 0.9300 . ? C5 C6 1.402(17) . ? C6 S1 1.782(12) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 C8 1.485(18) . ? C7 S1 1.792(12) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 N2 1.466(15) . ? C9 H9 0.9300 . ? C9 C10 1.367(16) . ? C9 N2 1.351(13) . ? C10 C11 1.352(17) . ? C11 H11 0.9300 . ? C11 N1 1.298(14) . ? C12 C13 1.357(18) . ? C12 C16 1.405(16) . ? C12 C17 1.503(19) . ? C12 Rh1 2.160(9) . ? C13 C14 1.35(2) . ? C13 C18 1.51(2) . ? C13 Rh1 2.161(11) . ? C14 C15 1.47(3) . ? C14 C19 1.53(3) . ? C14 Rh1 2.132(12) . ? C15 C16 1.44(2) . ? C15 C20 1.50(2) . ? C15 Rh1 2.119(12) . ? C16 C21 1.50(2) . ? C16 Rh1 2.162(10) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? Cl1 Rh1 2.385(3) . ? F1 P1 1.554(13) . ? F2 P1 1.478(14) . ? F3 P1 1.597(10) . ? F4 P1 1.478(14) . ? F5 P1 1.527(13) . ? F6 P1 1.561(10) . ? N1 N2 1.336(12) . ? N1 Rh1 2.127(9) . ? Rh1 S1 2.381(3) . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br1 C10 C11 N1 -179.9(8) . . . . ? C1 C2 C3 C4 3(3) . . . . ? C1 C6 S1 C7 -130.5(10) . . . . ? C1 C6 S1 Rh1 112.5(9) . . . . ? C2 C1 C6 C5 2(2) . . . . ? C2 C1 C6 S1 179.9(12) . . . . ? C2 C3 C4 C5 -1(3) . . . . ? C3 C4 C5 C6 0(2) . . . . ? C4 C5 C6 C1 0.0(19) . . . . ? C4 C5 C6 S1 -177.7(11) . . . . ? C5 C6 S1 C7 47.2(11) . . . . ? C5 C6 S1 Rh1 -69.7(11) . . . . ? C6 C1 C2 C3 -4(2) . . . . ? C7 C8 N2 C9 120.8(12) . . . . ? C7 C8 N2 N1 -60.6(14) . . . . ? C8 C7 S1 C6 -168.8(9) . . . . ? C8 C7 S1 Rh1 -46.9(10) . . . . ? C9 C10 C11 N1 -1.6(15) . . . . ? C10 C9 N2 C8 178.5(11) . . . . ? C10 C9 N2 N1 -0.2(12) . . . . ? C10 C11 N1 N2 1.4(13) . . . . ? C10 C11 N1 Rh1 -179.4(8) . . . . ? C11 N1 N2 C8 -179.6(11) . . . . ? C11 N1 N2 C9 -0.7(12) . . . . ? C12 C13 C14 C15 0.4(15) . . . . ? C12 C13 C14 C19 -178.3(16) . . . . ? C12 C13 C14 Rh1 61.1(9) . . . . ? C13 C12 C16 C15 -1.1(12) . . . . ? C13 C12 C16 C21 175.0(12) . . . . ? C13 C12 C16 Rh1 -61.2(8) . . . . ? C13 C14 C15 C16 -1.1(15) . . . . ? C13 C14 C15 C20 -174.4(14) . . . . ? C13 C14 C15 Rh1 62.9(9) . . . . ? C14 C15 C16 C12 1.3(13) . . . . ? C14 C15 C16 C21 -174.6(12) . . . . ? C14 C15 C16 Rh1 62.9(8) . . . . ? C16 C12 C13 C14 0.4(14) . . . . ? C16 C12 C13 C18 -176.5(14) . . . . ? C16 C12 C13 Rh1 60.8(7) . . . . ? C17 C12 C13 C14 174.0(12) . . . . ? C17 C12 C13 C18 -3(2) . . . . ? C17 C12 C13 Rh1 -125.6(12) . . . . ? C17 C12 C16 C15 -174.9(11) . . . . ? C17 C12 C16 C21 1.3(18) . . . . ? C17 C12 C16 Rh1 125.1(11) . . . . ? C18 C13 C14 C15 177.5(13) . . . . ? C18 C13 C14 C19 -1(3) . . . . ? C18 C13 C14 Rh1 -121.9(14) . . . . ? C19 C14 C15 C16 178.0(12) . . . . ? C19 C14 C15 C20 5(2) . . . . ? C19 C14 C15 Rh1 -118.1(13) . . . . ? C20 C15 C16 C12 175.0(14) . . . . ? C20 C15 C16 C21 -1(2) . . . . ? C20 C15 C16 Rh1 -123.4(16) . . . . ? N2 C9 C10 Br1 179.4(8) . . . . ? N2 C9 C10 C11 1.0(13) . . . . ? Rh1 C12 C13 C14 -60.4(9) . . . . ? Rh1 C12 C13 C18 122.7(15) . . . . ? Rh1 C12 C16 C15 60.1(7) . . . . ? Rh1 C12 C16 C21 -123.8(12) . . . . ? Rh1 C13 C14 C15 -60.6(9) . . . . ? Rh1 C13 C14 C19 120.6(19) . . . . ? Rh1 C14 C15 C16 -64.0(8) . . . . ? Rh1 C14 C15 C20 122.7(16) . . . . ? Rh1 C15 C16 C12 -61.6(7) . . . . ? Rh1 C15 C16 C21 122.5(13) . . . . ? Rh1 N1 N2 C8 1.4(14) . . . . ? Rh1 N1 N2 C9 -179.8(7) . . . . ? S1 C7 C8 N2 84.2(12) . . . . ?