#------------------------------------------------------------------------------ #$Date: 2020-04-03 03:48:29 +0300 (Fri, 03 Apr 2020) $ #$Revision: 249988 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/77/1557724.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_1557724 loop_ _publ_author_name 'Weder, Nicola' 'Probst, Benjamin' 'S\'every, Laurent' 'Fern\'andez-Ter\'an, Ricardo J.' 'Beckord, Jan' 'Blacque, Olivier' 'Tilley, S. David' 'Hamm, Peter' 'Osterwalder, J\"urg' 'Alberto, Roger' _publ_section_title ; Mechanistic insights into photocatalysis and over two days of stable H2 generation in electrocatalysis by a molecular cobalt catalyst immobilized on TiO2 ; _journal_name_full 'Catalysis Science & Technology' _journal_paper_doi 10.1039/D0CY00330A _journal_year 2020 _chemical_formula_moiety 'C24 H20 Br2 Co N4 O2, 2(C H4 O)' _chemical_formula_sum 'C26 H28 Br2 Co N4 O4' _chemical_formula_weight 679.27 _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 mixed _atom_sites_solution_primary dual _audit_creation_date 2017-11-07 _audit_creation_method ; Olex2 1.2 (compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381) ; _audit_update_record ; 2019-10-08 deposited with the CCDC. 2020-03-16 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.751(1) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 8.0833(1) _cell_length_b 11.8214(1) _cell_length_c 13.6272(1) _cell_measurement_reflns_used 16539 _cell_measurement_temperature 160(1) _cell_measurement_theta_max 78.7740 _cell_measurement_theta_min 4.9410 _cell_volume 1295.61(2) _computing_cell_refinement 'CrysAlisPro 1.171.39.13a (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.39.13a (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.39.13a (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015b)' _computing_structure_solution 'ShelXT (Sheldrick, 2015a)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 160(1) _diffrn_detector 'CCD plate' _diffrn_detector_type 'Pilatus 200K' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 36.00 124.00 0.50 3.00 -- 50.71 57.00 -30.00 176 2 \w 99.00 178.00 0.50 12.00 -- 107.75 111.00-120.00 158 3 \w 95.00 178.00 0.50 12.00 -- 107.75 15.00-120.00 166 4 \w 95.00 178.00 0.50 12.00 -- 107.75 15.00 -60.00 166 5 \w 95.00 178.00 0.50 12.00 -- 107.75 15.00 0.00 166 6 \w 95.00 178.00 0.50 12.00 -- 107.75 15.00-150.00 166 7 \w 91.00 178.00 0.50 12.00 -- 107.75 61.00 30.00 174 8 \w 94.00 178.00 0.50 12.00 -- 107.75 30.00 30.00 168 9 \w 94.00 178.00 0.50 12.00 -- 107.75 30.00 120.00 168 10 \w 94.00 178.00 0.50 12.00 -- 107.75 45.00 30.00 168 11 \w 94.00 178.00 0.50 12.00 -- 107.75 30.00 90.00 168 12 \w 94.00 178.00 0.50 12.00 -- 107.75 30.00 60.00 168 13 \w 94.00 178.00 0.50 12.00 -- 107.75 45.00 60.00 168 14 \w 92.00 178.00 0.50 12.00 -- 107.75 58.00 80.00 172 15 \w 31.00 108.00 0.50 12.00 -- 107.75 -94.00-180.00 154 16 \w 29.00 69.00 0.50 12.00 -- 107.75 -30.00-150.00 80 17 \w 32.00 77.00 0.50 12.00 -- 107.75 -45.00-150.00 90 18 \w 34.00 130.00 0.50 12.00 -- 107.75 -77.00-150.00 192 19 \w 31.00 115.00 0.50 12.00 -- 107.75-111.00-180.00 168 20 \w 32.00 77.00 0.50 12.00 -- 107.75 -45.00-180.00 90 21 \w 29.00 69.00 0.50 12.00 -- 107.75 -30.00 -90.00 80 22 \w 31.00 108.00 0.50 12.00 -- 107.75 -94.00-150.00 154 23 \w 31.00 115.00 0.50 12.00 -- 107.75-111.00 -60.00 168 24 \w 32.00 77.00 0.50 12.00 -- 107.75 -45.00 60.00 90 25 \w 31.00 115.00 0.50 12.00 -- 107.75-111.00 60.00 168 26 \w 32.00 77.00 0.50 12.00 -- 107.75 -45.00 150.00 90 27 \w 29.00 69.00 0.50 12.00 -- 107.75 -30.00 150.00 80 28 \w 31.00 108.00 0.50 12.00 -- 107.75 -94.00 90.00 154 29 \w 28.00 124.00 0.50 3.00 -- 50.71 77.00-120.00 192 30 \w 28.00 124.00 0.50 3.00 -- 50.71 77.00-180.00 192 31 \w -63.00 27.00 0.50 3.00 -- -50.71 38.00 -90.00 180 32 \w -66.00 22.00 0.50 3.00 -- -50.71 57.00 0.00 176 33 \w -63.00 27.00 0.50 3.00 -- -50.71 38.00-180.00 180 34 \w -90.00 -9.00 0.50 12.00 -- -86.25 111.00 -30.00 162 35 \w -128.00 -39.00 0.50 3.00 -- -50.71 -38.00 30.00 178 36 \w -127.00 -82.00 0.50 3.00 -- -50.71 -99.00-120.00 90 37 \w -127.00 -82.00 0.50 3.00 -- -50.71 -99.00-180.00 90 38 \w -162.00 -73.00 0.50 12.00 -- -86.25 -45.00 60.00 178 39 \w -160.00 -72.00 0.50 12.00 -- -86.25 -55.00 105.43 176 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, Pilatus 200K' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0781732000 _diffrn_orient_matrix_UB_12 0.0724497000 _diffrn_orient_matrix_UB_13 -0.0772511000 _diffrn_orient_matrix_UB_21 -0.1588910000 _diffrn_orient_matrix_UB_22 0.0725191000 _diffrn_orient_matrix_UB_23 -0.0139004000 _diffrn_orient_matrix_UB_31 0.0730712000 _diffrn_orient_matrix_UB_32 0.0804787000 _diffrn_orient_matrix_UB_33 0.0821273000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_unetI/netI 0.0174 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 26383 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.501 _diffrn_reflns_theta_min 4.963 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 9.148 _exptl_absorpt_correction_T_max 0.863 _exptl_absorpt_correction_T_min 0.477 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.13a (Rigaku Oxford Diffraction, 2015) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.741 _exptl_crystal_description needle _exptl_crystal_F_000 682 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.952 _refine_diff_density_min -0.487 _refine_diff_density_rms 0.090 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 177 _refine_ls_number_reflns 2644 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.081 _refine_ls_R_factor_all 0.0365 _refine_ls_R_factor_gt 0.0345 _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^)+(0.0513P)^2^+1.6856P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0928 _refine_ls_wR_factor_ref 0.0942 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2495 _reflns_number_total 2644 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0cy00330a2.cif _cod_data_source_block Co(II)-9 _cod_database_code 1557724 _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 0.838 _shelx_estimated_absorpt_t_min 0.305 _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, All O(H,H) groups 2. Restrained distances O1-H1 = O2-H2A 0.82 with sigma of 0.005 3.a Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9) 3.b Idealised Me refined as rotating group: C12(H12A,H12B,H12C), C13(H13A,H13B,H13C) ; _shelx_res_file ; TITL nico181017_a.res in P2(1)/n nico181017.res created by SHELXL-2017/1 at 13:25:56 on 07-Nov-2017 CELL 1.54184 8.0833 11.8214 13.6272 90 95.751 90 ZERR 2 0.0001 0.0001 0.0001 0 0.001 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Br Co N O UNIT 52 56 4 2 8 8 DFIX 0.82 0.005 O1 H1 O2 H2a L.S. 8 PLAN 20 SIZE 0.02 0.03 0.17 HTAB O1 O2 HTAB O2 Br1 BOND $H fmap 2 acta REM REM REM WGHT 0.051300 1.685600 FVAR 1.66021 BR1 3 0.621716 0.667954 0.384962 11.00000 0.02632 0.04500 = 0.03541 0.00876 0.00507 0.00245 C1 1 0.625159 0.314545 0.383537 11.00000 0.02902 0.03739 = 0.02952 -0.00474 0.00601 0.00277 C2 1 0.741589 0.230683 0.368931 11.00000 0.04147 0.03585 = 0.03907 -0.00709 0.01065 0.00567 AFIX 43 H2 2 0.720514 0.178672 0.318010 11.00000 -1.20000 AFIX 0 C3 1 0.886919 0.225029 0.429641 11.00000 0.03750 0.03687 = 0.05171 0.00009 0.00918 0.01173 AFIX 43 H3 2 0.964989 0.169338 0.420121 11.00000 -1.20000 AFIX 0 C4 1 0.916799 0.302607 0.505132 11.00000 0.02480 0.03759 = 0.04144 0.00624 0.00322 0.00561 AFIX 43 H4 2 1.014602 0.299948 0.547282 11.00000 -1.20000 AFIX 0 C5 1 0.797877 0.384284 0.516537 11.00000 0.02162 0.03255 = 0.02888 0.00682 0.00461 0.00046 C6 1 0.816482 0.471426 0.593255 11.00000 0.01992 0.03291 = 0.02690 0.00698 0.00198 -0.00053 C7 1 0.963502 0.491233 0.651773 11.00000 0.02025 0.03918 = 0.03502 0.00954 0.00092 -0.00213 AFIX 43 H7 2 1.057781 0.448177 0.644478 11.00000 -1.20000 AFIX 0 C8 1 0.967018 0.576181 0.721076 11.00000 0.02524 0.04908 = 0.03366 0.00478 -0.00599 -0.01095 AFIX 43 H8 2 1.064651 0.591953 0.760791 11.00000 -1.20000 AFIX 0 C9 1 0.825119 0.637577 0.731179 11.00000 0.03451 0.04423 = 0.02981 -0.00502 -0.00195 -0.00729 AFIX 43 H9 2 0.826159 0.694532 0.778315 11.00000 -1.20000 AFIX 0 C10 1 0.680086 0.614274 0.670733 11.00000 0.02938 0.03865 = 0.02631 -0.00369 -0.00026 -0.00136 C11 1 0.521025 0.674169 0.695504 11.00000 0.03517 0.04411 = 0.03434 -0.01039 0.00100 -0.00079 C12 1 0.456685 0.608303 0.782380 11.00000 0.03869 0.06929 = 0.03315 -0.00287 0.00521 0.00234 AFIX 137 H12A 2 0.543182 0.603872 0.835916 11.00000 -1.50000 H12B 2 0.424689 0.533341 0.761050 11.00000 -1.50000 H12C 2 0.362329 0.646896 0.803991 11.00000 -1.50000 AFIX 0 CO1 4 0.500000 0.500000 0.500000 10.50000 0.01821 0.03555 = 0.02324 -0.00501 -0.00072 0.00394 N1 5 0.676395 0.533790 0.601182 11.00000 0.02178 0.03440 = 0.02430 -0.00028 0.00192 0.00150 N2 5 0.652002 0.389248 0.457351 11.00000 0.02134 0.03459 = 0.02567 -0.00075 0.00223 0.00152 O1 6 0.564253 0.783492 0.732861 11.00000 0.04509 0.04955 = 0.05568 -0.02543 -0.00029 -0.00311 C13 1 0.711005 0.963370 0.510226 11.00000 0.09605 0.06504 = 0.08026 0.00039 0.00121 -0.00065 AFIX 137 H13A 2 0.628181 0.973292 0.455310 11.00000 -1.50000 H13B 2 0.819235 0.961393 0.486998 11.00000 -1.50000 H13C 2 0.705406 1.025196 0.555449 11.00000 -1.50000 AFIX 0 O2 6 0.681915 0.860888 0.558581 11.00000 0.09810 0.05634 = 0.06663 -0.00374 0.01058 -0.01502 H1 2 0.601219 0.807521 0.682687 11.00000 -1.50000 H2A 2 0.648499 0.815396 0.515512 11.00000 -1.50000 HKLF 4 REM nico181017_a.res in P2(1)/n REM R1 = 0.0345 for 2495 Fo > 4sig(Fo) and 0.0365 for all 2644 data REM 177 parameters refined using 2 restraints END WGHT 0.0516 1.6803 REM Highest difference peak 0.952, deepest hole -0.487, 1-sigma level 0.090 Q1 1 0.6585 0.7366 0.3965 11.00000 0.05 0.95 Q2 1 0.5863 0.6113 0.3403 11.00000 0.05 0.84 Q3 1 0.4585 0.4340 0.5177 11.00000 0.05 0.70 Q4 1 0.6354 0.6206 0.4351 11.00000 0.05 0.50 Q5 1 0.5804 0.9414 0.5201 11.00000 0.05 0.48 Q6 1 0.5430 0.7165 0.7819 11.00000 0.05 0.42 Q7 1 0.6524 0.8418 0.6428 11.00000 0.05 0.41 Q8 1 0.8050 0.4248 0.5552 11.00000 0.05 0.41 Q9 1 0.6147 0.3371 0.4379 11.00000 0.05 0.34 Q10 1 0.5842 0.7362 0.6628 11.00000 0.05 0.34 Q11 1 0.6997 0.2831 0.3660 11.00000 0.05 0.33 Q12 1 0.7545 0.5009 0.5972 11.00000 0.05 0.32 Q13 1 0.7281 0.3769 0.4912 11.00000 0.05 0.32 Q14 1 0.5620 0.7277 0.3424 11.00000 0.05 0.31 Q15 1 0.6707 0.5606 0.6537 11.00000 0.05 0.31 Q16 1 0.4916 0.4641 0.4438 11.00000 0.05 0.30 Q17 1 0.8923 0.4873 0.6213 11.00000 0.05 0.30 Q18 1 0.9312 0.5266 0.6851 11.00000 0.05 0.30 Q19 1 0.5362 0.7066 0.3772 11.00000 0.05 0.29 Q20 1 0.8403 0.3394 0.5159 11.00000 0.05 0.29 ; _shelx_res_checksum 70285 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 _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.62172(4) 0.66795(3) 0.38496(2) 0.03544(13) Uani 1 1 d . . . . . C1 C 0.6252(3) 0.3145(3) 0.3835(2) 0.0318(6) Uani 1 1 d . . . . . C2 C 0.7416(4) 0.2307(3) 0.3689(2) 0.0384(7) Uani 1 1 d . . . . . H2 H 0.720514 0.178672 0.318010 0.046 Uiso 1 1 calc R . . . . C3 C 0.8869(4) 0.2250(3) 0.4296(3) 0.0417(7) Uani 1 1 d . . . . . H3 H 0.964989 0.169338 0.420121 0.050 Uiso 1 1 calc R . . . . C4 C 0.9168(4) 0.3026(3) 0.5051(2) 0.0346(6) Uani 1 1 d . . . . . H4 H 1.014602 0.299948 0.547282 0.042 Uiso 1 1 calc R . . . . C5 C 0.7979(3) 0.3843(2) 0.5165(2) 0.0275(6) Uani 1 1 d . . . . . C6 C 0.8165(3) 0.4714(2) 0.5933(2) 0.0266(5) Uani 1 1 d . . . . . C7 C 0.9635(4) 0.4912(2) 0.6518(2) 0.0316(6) Uani 1 1 d . . . . . H7 H 1.057781 0.448177 0.644478 0.038 Uiso 1 1 calc R . . . . C8 C 0.9670(4) 0.5762(3) 0.7211(2) 0.0366(7) Uani 1 1 d . . . . . H8 H 1.064651 0.591953 0.760791 0.044 Uiso 1 1 calc R . . . . C9 C 0.8251(4) 0.6376(3) 0.7312(2) 0.0365(7) Uani 1 1 d . . . . . H9 H 0.826159 0.694532 0.778315 0.044 Uiso 1 1 calc R . . . . C10 C 0.6801(4) 0.6143(3) 0.6707(2) 0.0316(6) Uani 1 1 d . . . . . C11 C 0.5210(4) 0.6742(3) 0.6955(2) 0.0380(7) Uani 1 1 d . . . . . C12 C 0.4567(4) 0.6083(4) 0.7824(2) 0.0469(8) Uani 1 1 d . . . . . H12A H 0.543182 0.603872 0.835916 0.070 Uiso 1 1 calc GR . . . . H12B H 0.424689 0.533341 0.761050 0.070 Uiso 1 1 calc GR . . . . H12C H 0.362329 0.646896 0.803991 0.070 Uiso 1 1 calc GR . . . . Co1 Co 0.500000 0.500000 0.500000 0.02586(17) Uani 1 2 d S T P . . N1 N 0.6764(3) 0.5338(2) 0.60118(17) 0.0269(5) Uani 1 1 d . . . . . N2 N 0.6520(3) 0.3892(2) 0.45735(17) 0.0272(5) Uani 1 1 d . . . . . O1 O 0.5643(3) 0.7835(2) 0.7329(2) 0.0505(6) Uani 1 1 d D . . . . C13 C 0.7110(8) 0.9634(5) 0.5102(4) 0.0810(15) Uani 1 1 d . . . . . H13A H 0.628181 0.973292 0.455310 0.121 Uiso 1 1 calc GR . . . . H13B H 0.819235 0.961393 0.486998 0.121 Uiso 1 1 calc GR . . . . H13C H 0.705406 1.025196 0.555449 0.121 Uiso 1 1 calc GR . . . . O2 O 0.6819(5) 0.8609(3) 0.5586(3) 0.0735(9) Uani 1 1 d D . . . . H1 H 0.601(8) 0.808(5) 0.683(3) 0.110 Uiso 1 1 d DR . . . . H2A H 0.648(8) 0.815(4) 0.516(3) 0.110 Uiso 1 1 d DR . . . . 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 0.02632(18) 0.0450(2) 0.03541(19) 0.00876(13) 0.00507(12) 0.00245(12) C1 0.0290(15) 0.0374(15) 0.0295(14) -0.0047(11) 0.0060(12) 0.0028(11) C2 0.0415(17) 0.0358(15) 0.0391(16) -0.0071(13) 0.0106(13) 0.0057(13) C3 0.0375(16) 0.0369(16) 0.0517(19) 0.0001(14) 0.0092(14) 0.0117(13) C4 0.0248(14) 0.0376(16) 0.0414(16) 0.0062(13) 0.0032(12) 0.0056(12) C5 0.0216(12) 0.0326(14) 0.0289(13) 0.0068(11) 0.0046(10) 0.0005(11) C6 0.0199(12) 0.0329(13) 0.0269(13) 0.0070(11) 0.0020(10) -0.0005(11) C7 0.0203(13) 0.0392(16) 0.0350(15) 0.0095(12) 0.0009(11) -0.0021(11) C8 0.0252(14) 0.0491(18) 0.0337(15) 0.0048(13) -0.0060(11) -0.0110(13) C9 0.0345(16) 0.0442(17) 0.0298(15) -0.0050(13) -0.0020(12) -0.0073(13) C10 0.0294(14) 0.0386(15) 0.0263(14) -0.0037(11) -0.0003(11) -0.0014(12) C11 0.0352(16) 0.0441(17) 0.0343(16) -0.0104(13) 0.0010(13) -0.0008(13) C12 0.0387(17) 0.069(2) 0.0332(16) -0.0029(16) 0.0052(14) 0.0023(16) Co1 0.0182(3) 0.0356(4) 0.0232(3) -0.0050(2) -0.0007(2) 0.0039(2) N1 0.0218(11) 0.0344(12) 0.0243(11) -0.0003(9) 0.0019(9) 0.0015(9) N2 0.0213(10) 0.0346(12) 0.0257(11) -0.0007(9) 0.0022(9) 0.0015(9) O1 0.0451(14) 0.0495(14) 0.0557(16) -0.0254(12) -0.0003(12) -0.0031(11) C13 0.096(4) 0.065(3) 0.080(3) 0.000(3) 0.001(3) -0.001(3) O2 0.098(3) 0.0563(18) 0.067(2) -0.0037(15) 0.0106(19) -0.0150(18) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 1 0.0201 5 -1 -3 0.0701 -5 1 3 0.0861 0 1 -1 0.0044 0 -1 1 0.0124 0 -1 -1 0.0111 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 C11 116.6(3) . 3_666 ? N2 C1 C2 121.0(3) . . ? N2 C1 C11 121.9(3) . 3_666 ? C1 C2 H2 120.0 . . ? C3 C2 C1 119.9(3) . . ? C3 C2 H2 120.0 . . ? C2 C3 H3 120.2 . . ? C2 C3 C4 119.5(3) . . ? C4 C3 H3 120.2 . . ? C3 C4 H4 120.8 . . ? C3 C4 C5 118.4(3) . . ? C5 C4 H4 120.8 . . ? C4 C5 C6 123.3(3) . . ? N2 C5 C4 122.3(3) . . ? N2 C5 C6 114.4(2) . . ? C7 C6 C5 123.5(3) . . ? N1 C6 C5 114.2(2) . . ? N1 C6 C7 122.3(3) . . ? C6 C7 H7 120.8 . . ? C8 C7 C6 118.5(3) . . ? C8 C7 H7 120.8 . . ? C7 C8 H8 120.2 . . ? C9 C8 C7 119.6(3) . . ? C9 C8 H8 120.2 . . ? C8 C9 H9 120.1 . . ? C8 C9 C10 119.9(3) . . ? C10 C9 H9 120.1 . . ? C9 C10 C11 117.0(3) . . ? N1 C10 C9 121.1(3) . . ? N1 C10 C11 121.5(3) . . ? C1 C11 C10 119.5(3) 3_666 . ? C1 C11 C12 106.8(3) 3_666 . ? C10 C11 C12 106.8(3) . . ? O1 C11 C1 108.6(3) . 3_666 ? O1 C11 C10 108.5(3) . . ? O1 C11 C12 105.8(3) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? Br1 Co1 Br1 180.0 3_666 . ? N1 Co1 Br1 91.32(7) 3_666 . ? N1 Co1 Br1 88.68(7) . . ? N1 Co1 Br1 88.68(7) 3_666 3_666 ? N1 Co1 Br1 91.32(7) . 3_666 ? N1 Co1 N1 180.0 . 3_666 ? N1 Co1 N2 95.28(10) . 3_666 ? N1 Co1 N2 95.28(10) 3_666 . ? N1 Co1 N2 84.72(10) 3_666 3_666 ? N1 Co1 N2 84.72(10) . . ? N2 Co1 Br1 87.54(7) 3_666 . ? N2 Co1 Br1 87.54(7) . 3_666 ? N2 Co1 Br1 92.46(7) . . ? N2 Co1 Br1 92.46(7) 3_666 3_666 ? N2 Co1 N2 180.00(10) 3_666 . ? C6 N1 Co1 113.11(19) . . ? C10 N1 C6 118.6(2) . . ? C10 N1 Co1 128.0(2) . . ? C1 N2 C5 118.8(2) . . ? C1 N2 Co1 127.94(19) . . ? C5 N2 Co1 113.05(19) . . ? C11 O1 H1 96(5) . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O2 C13 H13A 109.5 . . ? O2 C13 H13B 109.5 . . ? O2 C13 H13C 109.5 . . ? C13 O2 H2A 107(5) . . ? 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 Co1 2.7707(3) . ? C1 C2 1.395(4) . ? C1 C11 1.523(4) 3_666 ? C1 N2 1.340(4) . ? C2 H2 0.9300 . ? C2 C3 1.369(5) . ? C3 H3 0.9300 . ? C3 C4 1.381(5) . ? C4 H4 0.9300 . ? C4 C5 1.382(4) . ? C5 C6 1.465(4) . ? C5 N2 1.362(3) . ? C6 C7 1.383(4) . ? C6 N1 1.365(4) . ? C7 H7 0.9300 . ? C7 C8 1.377(5) . ? C8 H8 0.9300 . ? C8 C9 1.376(5) . ? C9 H9 0.9300 . ? C9 C10 1.391(4) . ? C10 C11 1.535(4) . ? C10 N1 1.341(4) . ? C11 C12 1.550(5) . ? C11 O1 1.420(4) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? Co1 N1 1.923(2) 3_666 ? Co1 N1 1.923(2) . ? Co1 N2 1.925(2) 3_666 ? Co1 N2 1.925(2) . ? O1 H1 0.824(5) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C13 O2 1.410(6) . ? O2 H2A 0.821(5) . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O1 H1 O2 0.824(5) 1.976(8) 2.799(5) 177(7) . yes O2 H2A Br1 0.821(5) 2.484(18) 3.287(3) 166(7) . yes