#------------------------------------------------------------------------------ #$Date: 2021-01-14 05:39:40 +0200 (Thu, 14 Jan 2021) $ #$Revision: 260942 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/20/7242064.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_7242064 loop_ _publ_author_name 'Ma, Shuai' 'Cui, Jing-Wang' 'Rao, Caihui' 'Jia, Meng-Ze' 'Chen, Yun-Rui' 'Zhang, Jie' _publ_section_title ; Boosting Activity of Molecular Oxygen by Pyridinium-based Photocatalysts for Metal-free Alcohol Oxidation ; _journal_name_full 'Green Chemistry' _journal_paper_doi 10.1039/D0GC03730C _journal_year 2021 _chemical_formula_moiety 'C24 H27 Br3 N6' _chemical_formula_sum 'C24 H27 Br3 N6' _chemical_formula_weight 639.24 _space_group_crystal_system trigonal _space_group_IT_number 160 _space_group_name_Hall 'R 3 -2"' _space_group_name_H-M_alt 'R 3 m :H' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary dimap _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2020-09-25 deposited with the CCDC. 2021-01-11 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_formula_units_Z 3 _cell_length_a 16.647(3) _cell_length_b 16.647(3) _cell_length_c 7.749(3) _cell_measurement_reflns_used 299 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.2440 _cell_measurement_theta_min 4.5660 _cell_volume 1859.7(9) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) ; _computing_molecular_graphics 'DIAMOND. Version 3.0. Crystal Impact' _computing_publication_material 'Windows Word 2019' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 10.4159 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0537 _diffrn_reflns_av_unetI/netI 0.0549 _diffrn_reflns_Laue_measured_fraction_full 0.988 _diffrn_reflns_Laue_measured_fraction_max 0.985 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 1042 _diffrn_reflns_point_group_measured_fraction_full 0.738 _diffrn_reflns_point_group_measured_fraction_max 0.736 _diffrn_reflns_theta_full 24.985 _diffrn_reflns_theta_max 24.985 _diffrn_reflns_theta_min 3.861 _exptl_absorpt_coefficient_mu 4.906 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.57803 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour Gold-yellow _exptl_crystal_density_diffrn 1.712 _exptl_crystal_density_method 'not measured' _exptl_crystal_description rod _exptl_crystal_F_000 954 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 1.056 _refine_diff_density_min -0.944 _refine_diff_density_rms 0.229 _refine_ls_abs_structure_details ; Flack x determined using 139 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.02(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.886 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 56 _refine_ls_number_reflns 594 _refine_ls_number_restraints 28 _refine_ls_restrained_S_all 0.866 _refine_ls_R_factor_all 0.0752 _refine_ls_R_factor_gt 0.0518 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1901P)^2^+29.9483P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1470 _refine_ls_wR_factor_ref 0.2245 _reflns_Friedel_coverage 0.478 _reflns_Friedel_fraction_full 0.482 _reflns_Friedel_fraction_max 0.481 _reflns_number_gt 504 _reflns_number_total 594 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0gc03730c2.cif _cod_data_source_block TTEPY _cod_original_cell_volume 1859.6(9) _cod_database_code 7242064 _shelx_shelxl_version_number 2016/6 _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_res_file ; TITL 123_a.res in R3m 123.res created by SHELXL-2016/6 at 14:50:41 on 24-Sep-2020 CELL 0.71073 16.6468 16.6468 7.7488 90.000 90.000 120.000 ZERR 3.000 0.0030 0.0030 0.0025 0.000 0.000 0.000 LATT -3 SYMM -Y, X-Y, Z SYMM -X+Y, -X, Z SYMM -Y, -X, Z SYMM -X+Y, Y, Z SYMM X, X-Y, Z SFAC C H N Br UNIT 72 81 18 9 OMIT 0 50 L.S. 60 ACTA BOND FMAP 2 PLAN 20 FREE C2 C3 DFIX 1.38 0.001 C3 C4 C4 C5 N1 C3 ISOR 0.001 C1 ISOR 0.001 C2 ISOR 0.001 C3 ISOR 0.001 C4 WGHT 0.190100 29.948290 FVAR 0.31286 BR1 4 0.480265 0.519735 0.769866 10.50000 0.03641 0.03641 = 0.08221 -0.00114 0.00114 0.02046 N1 3 0.523335 0.476665 0.298711 10.50000 0.06112 0.06112 = 0.05991 -0.00195 0.00195 0.04624 N2 3 0.428420 0.714210 0.234156 10.50000 0.01582 0.02186 = 0.04082 0.00440 0.00880 0.00791 C1 1 0.583252 0.416748 0.505872 10.50000 0.07905 0.07905 = 0.07923 -0.00145 0.00145 0.04009 AFIX 137 H1A 2 0.606210 0.475887 0.561016 10.50000 -1.50000 H1B 2 0.625972 0.394733 0.524547 10.50000 -1.50000 H1C 2 0.523923 0.373275 0.553671 10.50000 -1.50000 AFIX 1 C2 1 0.573920 0.426080 0.327087 10.50000 0.05386 0.05386 = 0.05402 0.00020 -0.00020 0.02687 AFIX 23 H2A 2 0.540359 0.365225 0.274114 10.50000 -1.20000 H2B 2 0.634775 0.459641 0.274114 10.50000 -1.20000 AFIX 0 C3 1 0.575553 0.572109 0.289957 11.00000 0.04275 0.04344 = 0.04374 -0.00033 -0.00006 0.02182 AFIX 43 H3 2 0.639694 0.604478 0.302752 11.00000 -1.20000 AFIX 0 C4 1 0.524658 0.615537 0.260629 11.00000 0.02941 0.02891 = 0.02977 0.00020 0.00005 0.01465 AFIX 43 H4 2 0.557077 0.679686 0.247995 11.00000 -1.20000 AFIX 0 C5 1 0.429202 0.570798 0.248664 10.50000 0.04137 0.04137 = 0.03083 0.00071 -0.00071 0.02871 C6 1 0.378139 0.621861 0.237577 10.50000 0.02676 0.02676 = 0.03224 0.00450 -0.00450 0.01365 HKLF 4 REM 123_a.res in R3m REM R1 = 0.0518 for 504 Fo > 4sig(Fo) and 0.0752 for all 594 data REM 56 parameters refined using 28 restraints END WGHT 0.1611 0.0000 REM Highest difference peak 1.056, deepest hole -0.944, 1-sigma level 0.229 Q1 1 0.5636 0.4364 0.4206 10.50000 0.05 1.06 Q2 1 0.6023 0.3977 0.2768 10.50000 0.05 1.05 Q3 1 0.6653 0.5473 0.3640 11.00000 0.05 1.01 Q4 1 0.7354 0.4709 0.4880 10.50000 0.05 0.99 Q5 1 0.6012 0.3988 0.1797 10.50000 0.05 0.92 Q6 1 0.6349 0.3651 0.5120 10.50000 0.05 0.92 Q7 1 0.5656 0.5455 0.3440 11.00000 0.05 0.88 Q8 1 0.4996 0.5004 0.6763 10.50000 0.05 0.81 Q9 1 0.6245 0.3755 0.4479 10.50000 0.05 0.77 Q10 1 0.4491 0.4696 0.8289 11.00000 0.05 0.74 Q11 1 0.4632 0.5368 0.3960 10.50000 0.05 0.69 Q12 1 0.6379 0.7138 0.1702 11.00000 0.05 0.68 Q13 1 0.5914 0.4086 0.6521 10.50000 0.05 0.67 Q14 1 0.5477 0.6180 0.3346 11.00000 0.05 0.62 Q15 1 0.7327 0.6436 0.2461 11.00000 0.05 0.61 Q16 1 0.4989 0.3624 0.1434 11.00000 0.05 0.59 Q17 1 0.6986 0.3973 0.2554 10.50000 0.05 0.59 Q18 1 0.7297 0.6567 0.3571 11.00000 0.05 0.57 Q19 1 0.5462 0.4538 0.6987 10.50000 0.05 0.56 Q20 1 0.5423 0.3353 0.3702 11.00000 0.05 0.53 ; _shelx_res_checksum 21854 loop_ _space_group_symop_operation_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-y, -x, z' '-x+y, y, z' 'x, x-y, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' '-y+2/3, -x+1/3, z+1/3' '-x+y+2/3, y+1/3, z+1/3' 'x+2/3, x-y+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-y+1/3, -x+2/3, z+2/3' '-x+y+1/3, y+2/3, z+2/3' 'x+1/3, x-y+2/3, z+2/3' 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 0.48026(7) 0.51974(7) 0.7699(11) 0.0507(10) Uani 1 2 d S T P . . N1 N 0.5233(7) 0.4767(7) 0.299(4) 0.054(6) Uani 1 2 d DS T P . . N2 N 0.4284(11) 0.7142(5) 0.234(2) 0.027(3) Uani 1 2 d S T P . . C1 C 0.5833(14) 0.4167(14) 0.506(4) 0.079(5) Uani 1 2 d S TU P . . H1A H 0.606210 0.475887 0.561016 0.118 Uiso 0.5 1 calc R U P . . H1B H 0.625972 0.394733 0.524547 0.118 Uiso 0.5 1 calc R U P . . H1C H 0.523923 0.373275 0.553671 0.118 Uiso 0.5 1 calc R U P . . C2 C 0.573920 0.426080 0.327087 0.054 Uani 1 2 d S TU P . . H2A H 0.540359 0.365225 0.274114 0.065 Uiso 0.5 1 calc R U P . . H2B H 0.634775 0.459641 0.274114 0.065 Uiso 0.5 1 calc R U P . . C3 C 0.5756(12) 0.5721(6) 0.2900(17) 0.043(5) Uani 1 1 d D U . . . H3 H 0.639694 0.604478 0.302752 0.052 Uiso 1 1 calc R U . . . C4 C 0.5247(8) 0.6155(14) 0.2606(12) 0.029(4) Uani 1 1 d D U . . . H4 H 0.557077 0.679686 0.247995 0.035 Uiso 1 1 calc R U . . . C5 C 0.4292(7) 0.5708(7) 0.249(3) 0.034(5) Uani 1 2 d DS T P . . C6 C 0.3781(7) 0.6219(7) 0.238(3) 0.028(4) Uani 1 2 d S T P . . 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 0.0364(11) 0.0364(11) 0.0822(16) -0.0011(6) 0.0011(6) 0.0205(11) N1 0.061(13) 0.061(13) 0.060(13) -0.002(5) 0.002(5) 0.046(13) N2 0.016(9) 0.022(6) 0.041(8) 0.004(3) 0.009(7) 0.008(4) C1 0.079(5) 0.079(5) 0.079(5) -0.0015(18) 0.0015(18) 0.040(3) C2 0.054 0.054 0.054 0.000 0.000 0.027 C3 0.043(5) 0.043(5) 0.044(5) -0.0003(13) -0.0001(13) 0.022(3) C4 0.029(4) 0.029(4) 0.030(4) 0.0002(13) 0.0000(13) 0.015(2) C5 0.041(10) 0.041(10) 0.031(9) 0.001(4) -0.001(4) 0.029(11) C6 0.027(8) 0.027(8) 0.032(8) 0.005(4) -0.005(4) 0.014(9) 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' Br Br -0.2901 2.4595 '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 C3 N1 C3 126(3) . 4_665 ? C3 N1 C2 117.0(13) . . ? C3 N1 C2 117.0(13) 4_665 . ? C6 N2 C6 114.1(19) 2_665 . ? C1 C2 N1 109.6(19) . . ? N1 C3 C4 114(2) . . ? C3 C4 C5 125(2) . . ? C4 C5 C4 115(3) . 4_665 ? C4 C5 C6 122.2(13) . . ? C4 C5 C6 122.2(13) 4_665 . ? N2 C6 N2 125.8(19) . 3_565 ? N2 C6 C5 117.1(10) . . ? N2 C6 C5 117.1(10) 3_565 . ? 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 N1 C3 1.3797(13) . ? N1 C3 1.3797(13) 4_665 ? N1 C2 1.47(2) . ? N2 C6 1.333(12) 2_665 ? N2 C6 1.333(12) . ? C1 C2 1.41(3) . ? C3 C4 1.3801(13) . ? C4 C5 1.3802(13) . ? C5 C6 1.47(3) . ?