#------------------------------------------------------------------------------ #$Date: 2024-01-06 09:53:43 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288773 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/75/7247585.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_7247585 loop_ _publ_author_name 'Sobczak, Paulina' 'Siera\'nski, Tomasz' '\'Swi\;atkowski, Marcin' 'Trz\;esowska-Kruszy\'nska, Agata' _publ_section_title ; New Schiff base salts as sources of blue and green light in the solid state: the role of the anion and protonation ; _journal_issue 44 _journal_name_full CrystEngComm _journal_page_first 6185 _journal_page_last 6193 _journal_paper_doi 10.1039/D3CE00758H _journal_volume 25 _journal_year 2023 _chemical_formula_moiety 'C15 H13 N O3' _chemical_formula_sum 'C15 H13 N O3' _chemical_formula_weight 255.26 _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 _audit_creation_date 2022-12-06 _audit_creation_method ; Olex2 1.5-ac5-024 (compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498) ; _audit_update_record ; 2023-07-28 deposited with the CCDC. 2023-10-25 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.4431(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 3.82566(3) _cell_length_b 15.07160(6) _cell_length_c 21.19950(9) _cell_measurement_reflns_used 68442 _cell_measurement_temperature 100.01(10) _cell_measurement_theta_max 78.7130 _cell_measurement_theta_min 3.5740 _cell_volume 1221.227(12) _computing_cell_refinement 'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)' _computing_data_collection 'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)' _computing_data_reduction 'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)' _computing_molecular_graphics 'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.01(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 5.8140 _diffrn_detector_type 'Pilatus 300K' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.996 _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 -25.00 26.00 0.50 0.10 -- 49.71 -19.00-180.00 102 2 \w -43.00 24.00 0.50 0.10 -- -50.71 38.00 -60.00 134 3 \w -26.00 25.00 0.50 0.10 -- -50.71 19.00 0.00 102 4 \w -26.00 25.00 0.50 0.10 -- -50.71 19.00 150.00 102 5 \w -26.00 25.00 0.50 0.10 -- -50.71 19.00-120.00 102 6 \w -26.00 25.00 0.50 0.10 -- -50.71 19.00-150.00 102 7 \w -43.00 -11.00 0.50 0.22 -- -86.25 38.00 -60.00 64 8 \w -43.00 -11.00 0.50 0.22 -- -86.25 38.00 60.00 64 9 \w -43.00 -11.00 0.50 0.22 -- -86.25 38.00 90.00 64 10 \w -158.00 -73.00 0.50 0.22 -- -86.25-125.00 30.00 170 11 \w -43.00 -11.00 0.50 0.22 -- -86.25 38.00 30.00 64 12 \w -43.00 -11.00 0.50 0.22 -- -86.25 38.00 -30.00 64 13 \w 39.00 107.00 0.50 0.22 -- 107.75 -99.00 -60.00 136 14 \w 39.00 107.00 0.50 0.22 -- 107.75 -99.00 120.00 136 15 \w 38.00 117.00 0.50 0.22 -- 107.75-132.00 -55.00 158 16 \w 37.00 66.00 0.50 0.22 -- 107.75 -57.00 -60.00 58 17 \w 43.00 105.00 0.50 0.22 -- 107.75 -77.00 120.00 124 18 \w 97.00 178.00 0.50 0.22 -- 107.75 19.00-150.00 162 19 \w 37.00 66.00 0.50 0.22 -- 107.75 -57.00 -90.00 58 20 \w 27.00 114.00 0.50 0.10 -- 49.71 77.00 150.00 174 21 \w 27.00 114.00 0.50 0.10 -- 49.71 77.00 -60.00 174 22 \w 60.00 121.00 0.50 0.10 -- 49.71-178.00-180.00 122 23 \w 27.00 114.00 0.50 0.10 -- 49.71 77.00 30.00 174 24 \w -115.00 -28.00 0.50 0.10 -- -50.71 -77.00 -90.00 174 25 \w -157.00 -71.00 0.50 0.22 -- -86.25 -57.00 -30.00 172 26 \w -151.00 -64.00 0.50 0.22 -- -86.25 -77.00 -60.00 174 27 \w -151.00 -64.00 0.50 0.22 -- -86.25 -77.00 120.00 174 28 \w -151.00 -64.00 0.50 0.22 -- -86.25 -77.00 30.00 174 29 \w -151.00 -64.00 0.50 0.22 -- -86.25 -77.00-180.00 174 30 \w -151.00 -64.00 0.50 0.22 -- -86.25 -77.00-120.00 174 31 \w 97.00 178.00 0.50 0.22 -- 107.75 38.00 -90.00 162 32 \w 37.00 165.00 0.50 0.22 -- 107.75 0.00 120.00 256 33 \w 37.00 66.00 0.50 0.22 -- 107.75 -57.00-180.00 58 34 \w 39.00 107.00 0.50 0.22 -- 107.75 -99.00 30.00 136 35 \w 27.00 114.00 0.50 0.10 -- 49.71 77.00 120.00 174 36 \w 27.00 114.00 0.50 0.10 -- 49.71 77.00-150.00 174 37 \w 35.00 121.00 0.50 0.10 -- 49.71 57.00 -60.00 172 38 \w -115.00 -28.00 0.50 0.10 -- -50.71 -77.00 30.00 174 39 \w -125.00 -40.00 0.50 0.10 -- -50.71 -38.00 150.00 170 40 \w -151.00 -64.00 0.50 0.22 -- -86.25 -77.00 60.00 174 41 \w -151.00 -64.00 0.50 0.22 -- -86.25 -77.00-150.00 174 42 \w -151.00 -64.00 0.50 0.22 -- -86.25 -77.00 0.00 174 43 \w -43.00 -11.00 0.50 0.22 -- -86.25 38.00 120.00 64 44 \w -151.00 -64.00 0.50 0.22 -- -86.25 -77.00 90.00 174 45 \w -151.00 -64.00 0.50 0.22 -- -86.25 -77.00 150.00 174 46 \w -151.00 -64.00 0.50 0.22 -- -86.25 -77.00 -90.00 174 47 \w 43.00 105.00 0.50 0.22 -- 107.75 -77.00 0.00 124 48 \w 37.00 66.00 0.50 0.22 -- 107.75 -57.00 30.00 58 49 \w 37.00 66.00 0.50 0.22 -- 107.75 -57.00 150.00 58 50 \w 62.00 120.00 0.50 0.10 -- 49.71 178.00 60.00 116 51 \w -125.00 -40.00 0.50 0.10 -- -50.71 -38.00 -90.00 170 52 \w -115.00 -28.00 0.50 0.10 -- -50.71 -77.00 120.00 174 53 \w -125.00 -40.00 0.50 0.10 -- -50.71 -38.00 60.00 170 54 \w -125.00 -40.00 0.50 0.10 -- -50.71 -38.00-180.00 170 55 \w -151.00 -64.00 0.50 0.22 -- -86.25 -77.00 -30.00 174 56 \w 37.00 66.00 0.50 0.22 -- 107.75 -57.00 90.00 58 57 \w 85.00 172.00 0.50 0.22 -- 107.75 77.00 60.00 174 58 \w 94.00 178.00 0.50 0.22 -- 107.75 125.00 -30.00 168 59 \w 85.00 172.00 0.50 0.22 -- 107.75 77.00 -30.00 174 60 \w 37.00 66.00 0.50 0.22 -- 107.75 -57.00 120.00 58 61 \w 39.00 107.00 0.50 0.22 -- 107.75 -99.00 60.00 136 62 \w 85.00 172.00 0.50 0.22 -- 107.75 77.00-150.00 174 63 \w 85.00 172.00 0.50 0.22 -- 107.75 77.00 30.00 174 64 \w 85.00 172.00 0.50 0.22 -- 107.75 77.00 120.00 174 65 \w 35.00 121.00 0.50 0.10 -- 49.71 57.00 120.00 172 66 \w 35.00 121.00 0.50 0.10 -- 49.71 57.00 -30.00 172 67 \w 35.00 121.00 0.50 0.10 -- 49.71 57.00 30.00 172 68 \w 39.00 124.00 0.50 0.10 -- 49.71 38.00 -60.00 170 69 \w -125.00 -40.00 0.50 0.10 -- -50.71 -38.00-120.00 170 70 \w -157.00 -71.00 0.50 0.22 -- -86.25 -57.00 30.00 172 71 \w -161.00 -76.00 0.50 0.22 -- -86.25 -38.00-150.00 170 72 \w -157.00 -71.00 0.50 0.22 -- -86.25 -57.00-180.00 172 73 \w -157.00 -71.00 0.50 0.22 -- -86.25 -57.00 0.00 172 74 \w -158.00 -73.00 0.50 0.22 -- -86.25-125.00-150.00 170 75 \w -161.00 -76.00 0.50 0.22 -- -86.25 -38.00 -90.00 170 76 \w 43.00 105.00 0.50 0.22 -- 107.75 -77.00 -60.00 124 77 \w 93.00 178.00 0.50 0.22 -- 107.75 57.00-180.00 170 78 \w 37.00 66.00 0.50 0.22 -- 107.75 -57.00-150.00 58 79 \w 85.00 172.00 0.50 0.22 -- 107.75 77.00 90.00 174 80 \w 35.00 121.00 0.50 0.10 -- 49.71 57.00-180.00 172 81 \w -25.00 26.00 0.50 0.10 -- 49.71 -19.00 150.00 102 82 \w -125.00 -40.00 0.50 0.10 -- -50.71 -38.00 30.00 170 83 \w -115.00 -28.00 0.50 0.10 -- -50.71 -77.00 -30.00 174 84 \w -125.00 -40.00 0.50 0.10 -- -50.71 -38.00-150.00 170 85 \w -157.00 -71.00 0.50 0.22 -- -86.25 -57.00 120.00 172 86 \w 93.00 178.00 0.50 0.22 -- 107.75 57.00 60.00 170 87 \w 37.00 165.00 0.50 0.22 -- 107.75 0.00-180.00 256 88 \w 93.00 178.00 0.50 0.22 -- 107.75 57.00 -60.00 170 89 \w 85.00 172.00 0.50 0.22 -- 107.75 77.00 0.00 174 90 \w 85.00 172.00 0.50 0.22 -- 107.75 77.00 -90.00 174 91 \w 37.00 165.00 0.50 0.22 -- 107.75 0.00-150.00 256 92 \w 37.00 165.00 0.50 0.22 -- 107.75 0.00-120.00 256 93 \w 37.00 165.00 0.50 0.22 -- 107.75 0.00 -90.00 256 94 \w 85.00 172.00 0.50 0.22 -- 107.75 77.00-120.00 174 95 \w -122.00 -36.00 0.50 0.10 -- -50.71 -57.00 90.00 172 96 \w -126.00 -40.00 0.50 0.10 -- -50.71 -19.00 90.00 172 97 \w -126.00 -40.00 0.50 0.10 -- -50.71 -19.00 -90.00 172 98 \w -126.00 -40.00 0.50 0.10 -- -50.71 -19.00 30.00 172 99 \w -126.00 -40.00 0.50 0.10 -- -50.71 -19.00 -30.00 172 100 \w 37.00 165.00 0.50 0.22 -- 107.75 0.00 -30.00 256 101 \w 37.00 165.00 0.50 0.22 -- 107.75 0.00 150.00 256 102 \w 37.00 165.00 0.50 0.22 -- 107.75 0.00 -60.00 256 103 \w 37.00 165.00 0.50 0.22 -- 107.75 0.00 90.00 256 104 \w 37.00 165.00 0.50 0.22 -- 107.75 0.00 60.00 256 105 \w 37.00 165.00 0.50 0.22 -- 107.75 0.00 30.00 256 106 \w 37.00 165.00 0.50 0.22 -- 107.75 0.00-180.00 256 107 \w 37.00 165.00 0.50 0.22 -- 107.75 0.00-150.00 256 108 \w 37.00 165.00 0.50 0.22 -- 107.75 0.00-120.00 256 109 \w 37.00 165.00 0.50 0.22 -- 107.75 0.00 0.00 256 110 \w -21.00 106.00 0.50 0.10 -- 49.71 0.00-180.00 254 111 \w -21.00 106.00 0.50 0.10 -- 49.71 0.00 -60.00 254 112 \w -115.00 -28.00 0.50 0.10 -- -50.71 -77.00 60.00 174 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, Pilatus 300K' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0287775000 _diffrn_orient_matrix_UB_12 0.0350233000 _diffrn_orient_matrix_UB_13 -0.0682860000 _diffrn_orient_matrix_UB_21 -0.0556721000 _diffrn_orient_matrix_UB_22 0.0947184000 _diffrn_orient_matrix_UB_23 0.0249828000 _diffrn_orient_matrix_UB_31 0.3981935000 _diffrn_orient_matrix_UB_32 0.0157831000 _diffrn_orient_matrix_UB_33 0.0016933000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0490 _diffrn_reflns_av_unetI/netI 0.0109 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 85187 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 78.910 _diffrn_reflns_theta_min 3.599 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.800 _exptl_absorpt_correction_T_max 0.945 _exptl_absorpt_correction_T_min 0.865 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.68a (Rigaku Oxford Diffraction, 2022) 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 colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.388 _exptl_crystal_description block _exptl_crystal_F_000 536 _exptl_crystal_size_max 0.221 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.086 _refine_diff_density_max 0.247 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 174 _refine_ls_number_reflns 2622 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.057 _refine_ls_R_factor_all 0.0346 _refine_ls_R_factor_gt 0.0339 _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^)+(0.0432P)^2^+0.4861P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0887 _refine_ls_wR_factor_ref 0.0893 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2533 _reflns_number_total 2622 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00758h2.cif _cod_data_source_block ps010-no3pl _cod_depositor_comments 'Adding full bibliography for 7247579--7247585.cif.' _cod_original_cell_volume 1221.225(11) _cod_database_code 7247585 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C15 H13 N1 O3' _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 0.934 _shelx_estimated_absorpt_t_min 0.843 _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) groups 2.a Aromatic/amide H refined with riding coordinates: C10(H10), C11(H11), C7(H7), C6(H6), C4(H4), C14(H14), C13(H13), C3(H3), C8(H8) 2.b Idealised Me refined as rotating group: C15(H15A,H15B,H15C) 2.c Idealised tetrahedral OH refined as rotating group: O1(H1) ; _shelx_res_file ; TITL ps010-no3pl_a.res in P2(1)/c ps010-no3pl.res created by SHELXL-2018/3 at 16:59:11 on 06-Dec-2022 REM Old TITL ps010-NO3pl in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.104, Rweak 0.006, Alpha 0.015 REM 1.269 for 107 systematic absences, Orientation as input REM Formula found by SHELXT: C15 N O3 CELL 1.54184 3.825655 15.071598 21.199496 90 92.4431 90 ZERR 4 0.000028 0.000061 0.000085 0 0.0005 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 60 52 4 12 L.S. 10 PLAN 20 SIZE 0.086 0.2 0.221 TEMP -173 CONF BOND list 4 MORE -1 fmap 2 53 acta BOND $H REM REM REM WGHT 0.043200 0.486100 FVAR 0.69316 O3 4 0.596880 0.136984 0.721281 11.00000 0.02788 0.01624 = 0.01986 0.00226 0.00363 -0.00095 O1 4 0.830918 0.941477 0.565852 11.00000 0.04354 0.01443 = 0.02315 -0.00155 0.01282 -0.00049 AFIX 147 H1 2 0.869709 0.991866 0.550729 11.00000 -1.50000 AFIX 0 O2 4 1.047028 0.897929 0.474332 11.00000 0.03863 0.01732 = 0.01980 0.00098 0.01027 -0.00048 N1 3 0.736956 0.521198 0.597097 11.00000 0.01980 0.01614 = 0.01665 0.00034 0.00218 -0.00037 C5 1 0.789849 0.611185 0.582515 11.00000 0.01564 0.01675 = 0.01472 0.00023 -0.00188 -0.00117 C12 1 0.630239 0.223183 0.702045 11.00000 0.01661 0.01650 = 0.01735 0.00127 0.00585 0.00151 C10 1 0.856341 0.367689 0.729609 11.00000 0.01639 0.02002 = 0.01515 -0.00177 0.00112 0.00065 AFIX 43 H10 2 0.974299 0.405907 0.759110 11.00000 -1.20000 AFIX 0 C11 1 0.801964 0.279717 0.745227 11.00000 0.01800 0.02160 = 0.01372 0.00213 0.00161 0.00226 AFIX 43 H11 2 0.881614 0.257877 0.785347 11.00000 -1.20000 AFIX 0 C7 1 0.982292 0.719175 0.507688 11.00000 0.01765 0.01904 = 0.01328 0.00006 0.00117 0.00017 AFIX 43 H7 2 1.087924 0.732853 0.469119 11.00000 -1.20000 AFIX 0 C6 1 0.939671 0.631507 0.525051 11.00000 0.01944 0.01696 = 0.01431 -0.00199 0.00023 0.00106 AFIX 43 H6 2 1.011701 0.585195 0.498120 11.00000 -1.20000 AFIX 0 C4 1 0.677957 0.679813 0.621415 11.00000 0.01724 0.01926 = 0.01330 0.00039 0.00114 -0.00045 AFIX 43 H4 2 0.574607 0.666228 0.660213 11.00000 -1.20000 AFIX 0 C9 1 0.739019 0.400898 0.670690 11.00000 0.01490 0.01756 = 0.01575 -0.00033 0.00315 0.00126 C14 1 0.560912 0.343644 0.628625 11.00000 0.01763 0.01997 = 0.01330 0.00047 0.00153 0.00138 AFIX 43 H14 2 0.475364 0.365786 0.588949 11.00000 -1.20000 AFIX 0 C13 1 0.506162 0.255330 0.643431 11.00000 0.01735 0.01974 = 0.01519 -0.00189 0.00272 -0.00042 AFIX 43 H13 2 0.386021 0.217174 0.614168 11.00000 -1.20000 AFIX 0 C3 1 0.717908 0.767605 0.603341 11.00000 0.01741 0.01782 = 0.01465 -0.00169 0.00085 0.00085 AFIX 43 H3 2 0.640937 0.814032 0.629695 11.00000 -1.20000 AFIX 0 C2 1 0.871306 0.787814 0.546391 11.00000 0.01636 0.01618 = 0.01488 -0.00011 -0.00013 0.00015 C8 1 0.808816 0.493001 0.652973 11.00000 0.01562 0.01822 = 0.01665 -0.00167 0.00156 0.00032 AFIX 43 H8 2 0.909378 0.532467 0.683616 11.00000 -1.20000 AFIX 0 C1 1 0.922764 0.880257 0.525907 11.00000 0.02025 0.01802 = 0.01653 -0.00066 0.00205 0.00029 C15 1 0.434403 0.076233 0.677187 11.00000 0.02558 0.01832 = 0.02806 -0.00164 0.00486 -0.00272 AFIX 137 H15A 2 0.556335 0.078087 0.637481 11.00000 -1.50000 H15B 2 0.188923 0.092983 0.669272 11.00000 -1.50000 H15C 2 0.446713 0.016038 0.694621 11.00000 -1.50000 AFIX 0 HKLF 4 REM ps010-no3pl_a.res in P2(1)/c REM wR2 = 0.0893, GooF = S = 1.057, Restrained GooF = 1.057 for all data REM R1 = 0.0339 for 2533 Fo > 4sig(Fo) and 0.0346 for all 2622 data REM 174 parameters refined using 0 restraints END WGHT 0.0432 0.4860 REM Highest difference peak 0.247, deepest hole -0.200, 1-sigma level 0.042 Q1 1 0.7301 0.6428 0.6023 11.00000 0.05 0.25 Q2 1 0.8914 0.8329 0.5383 11.00000 0.05 0.24 Q3 1 0.7947 0.4418 0.6598 11.00000 0.05 0.24 Q4 1 0.8999 0.6228 0.5589 11.00000 0.05 0.23 Q5 1 0.8486 0.7787 0.5783 11.00000 0.05 0.23 Q6 1 0.8927 0.7567 0.5235 11.00000 0.05 0.23 Q7 1 0.5208 0.2417 0.6789 11.00000 0.05 0.20 Q8 1 0.5679 0.3790 0.6590 11.00000 0.05 0.20 Q9 1 0.9629 0.6781 0.5201 11.00000 0.05 0.20 Q10 1 0.7309 0.7211 0.6154 11.00000 0.05 0.19 Q11 1 0.9796 0.7566 0.5331 11.00000 0.05 0.18 Q12 1 0.7462 0.3647 0.6429 11.00000 0.05 0.18 Q13 1 0.7722 0.3836 0.7005 11.00000 0.05 0.18 Q14 1 0.8012 0.2435 0.7170 11.00000 0.05 0.17 Q15 1 0.6335 0.2581 0.7281 11.00000 0.05 0.17 Q16 1 0.6459 0.7197 0.6069 11.00000 0.05 0.17 Q17 1 0.5046 0.3003 0.6434 11.00000 0.05 0.16 Q18 1 0.7166 0.7791 0.5664 11.00000 0.05 0.16 Q19 1 0.7632 0.5625 0.5965 11.00000 0.05 0.14 Q20 1 1.0597 0.9504 0.4623 11.00000 0.05 0.14 ; _shelx_res_checksum 98530 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.452 _oxdiff_exptl_absorpt_empirical_full_min 0.703 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_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O3 O 0.5969(2) 0.13698(5) 0.72128(3) 0.02125(18) Uani 1 1 d . . . . . O1 O 0.8309(2) 0.94148(5) 0.56585(4) 0.0267(2) Uani 1 1 d . . . . . H1 H 0.869709 0.991866 0.550729 0.040 Uiso 1 1 calc R U . . . O2 O 1.0470(2) 0.89793(5) 0.47433(4) 0.02499(19) Uani 1 1 d . . . . . N1 N 0.7370(2) 0.52120(6) 0.59710(4) 0.01749(19) Uani 1 1 d . . . . . C5 C 0.7898(3) 0.61119(6) 0.58251(4) 0.0158(2) Uani 1 1 d . . . . . C12 C 0.6302(3) 0.22318(6) 0.70204(5) 0.0167(2) Uani 1 1 d . . . . . C10 C 0.8563(3) 0.36769(7) 0.72961(5) 0.0172(2) Uani 1 1 d . . . . . H10 H 0.974299 0.405907 0.759110 0.021 Uiso 1 1 calc R U . . . C11 C 0.8020(3) 0.27972(7) 0.74523(5) 0.0177(2) Uani 1 1 d . . . . . H11 H 0.881614 0.257877 0.785347 0.021 Uiso 1 1 calc R U . . . C7 C 0.9823(3) 0.71917(7) 0.50769(4) 0.0166(2) Uani 1 1 d . . . . . H7 H 1.087924 0.732853 0.469119 0.020 Uiso 1 1 calc R U . . . C6 C 0.9397(3) 0.63151(6) 0.52505(4) 0.0169(2) Uani 1 1 d . . . . . H6 H 1.011701 0.585195 0.498120 0.020 Uiso 1 1 calc R U . . . C4 C 0.6780(3) 0.67981(7) 0.62141(4) 0.0166(2) Uani 1 1 d . . . . . H4 H 0.574607 0.666228 0.660213 0.020 Uiso 1 1 calc R U . . . C9 C 0.7390(3) 0.40090(6) 0.67069(4) 0.0160(2) Uani 1 1 d . . . . . C14 C 0.5609(3) 0.34364(7) 0.62863(5) 0.0169(2) Uani 1 1 d . . . . . H14 H 0.475364 0.365786 0.588949 0.020 Uiso 1 1 calc R U . . . C13 C 0.5062(3) 0.25533(7) 0.64343(5) 0.0174(2) Uani 1 1 d . . . . . H13 H 0.386021 0.217174 0.614168 0.021 Uiso 1 1 calc R U . . . C3 C 0.7179(3) 0.76760(7) 0.60334(5) 0.0166(2) Uani 1 1 d . . . . . H3 H 0.640937 0.814032 0.629695 0.020 Uiso 1 1 calc R U . . . C2 C 0.8713(3) 0.78781(6) 0.54639(4) 0.0158(2) Uani 1 1 d . . . . . C8 C 0.8088(3) 0.49300(7) 0.65297(5) 0.0168(2) Uani 1 1 d . . . . . H8 H 0.909378 0.532467 0.683616 0.020 Uiso 1 1 calc R U . . . C1 C 0.9228(3) 0.88026(7) 0.52591(5) 0.0182(2) Uani 1 1 d . . . . . C15 C 0.4344(3) 0.07623(7) 0.67719(5) 0.0239(2) Uani 1 1 d . . . . . H15A H 0.556335 0.078087 0.637481 0.036 Uiso 1 1 calc R U . . . H15B H 0.188923 0.092983 0.669272 0.036 Uiso 1 1 calc R U . . . H15C H 0.446713 0.016038 0.694621 0.036 Uiso 1 1 calc R U . . . 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 O3 0.0279(4) 0.0162(4) 0.0199(4) 0.0023(3) 0.0036(3) -0.0009(3) O1 0.0435(5) 0.0144(4) 0.0231(4) -0.0015(3) 0.0128(3) -0.0005(3) O2 0.0386(5) 0.0173(4) 0.0198(4) 0.0010(3) 0.0103(3) -0.0005(3) N1 0.0198(4) 0.0161(4) 0.0167(4) 0.0003(3) 0.0022(3) -0.0004(3) C5 0.0156(5) 0.0167(5) 0.0147(4) 0.0002(4) -0.0019(3) -0.0012(4) C12 0.0166(5) 0.0165(5) 0.0173(5) 0.0013(4) 0.0059(4) 0.0015(4) C10 0.0164(5) 0.0200(5) 0.0152(5) -0.0018(4) 0.0011(4) 0.0007(4) C11 0.0180(5) 0.0216(5) 0.0137(4) 0.0021(4) 0.0016(4) 0.0023(4) C7 0.0176(5) 0.0190(5) 0.0133(4) 0.0001(3) 0.0012(3) 0.0002(4) C6 0.0194(5) 0.0170(5) 0.0143(5) -0.0020(4) 0.0002(4) 0.0011(4) C4 0.0172(5) 0.0193(5) 0.0133(4) 0.0004(4) 0.0011(3) -0.0005(4) C9 0.0149(5) 0.0176(5) 0.0158(4) -0.0003(4) 0.0032(4) 0.0013(4) C14 0.0176(5) 0.0200(5) 0.0133(4) 0.0005(4) 0.0015(3) 0.0014(4) C13 0.0173(5) 0.0197(5) 0.0152(4) -0.0019(4) 0.0027(4) -0.0004(4) C3 0.0174(5) 0.0178(5) 0.0147(4) -0.0017(4) 0.0008(4) 0.0009(4) C2 0.0164(5) 0.0162(5) 0.0149(4) -0.0001(3) -0.0001(3) 0.0002(4) C8 0.0156(5) 0.0182(5) 0.0167(5) -0.0017(4) 0.0016(4) 0.0003(4) C1 0.0203(5) 0.0180(5) 0.0165(5) -0.0007(4) 0.0020(4) 0.0003(4) C15 0.0256(6) 0.0183(5) 0.0281(5) -0.0016(4) 0.0049(4) -0.0027(4) 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' 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 -10 -2 0.0861 2 0 -1 0.1068 -2 0 1 0.1068 0 10 2 0.1095 0 1 -14 0.0492 0 -1 14 0.0328 2 0 10 0.0626 2 1 5 0.0903 -2 0 -9 0.1012 0 5 12 0.0523 0 -5 -12 0.0730 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 C12 O3 C15 117.12(8) . . ? C1 O1 H1 109.5 . . ? C8 N1 C5 119.80(9) . . ? C6 C5 N1 117.98(9) . . ? C4 C5 N1 122.12(9) . . ? C4 C5 C6 119.77(9) . . ? O3 C12 C11 115.56(9) . . ? O3 C12 C13 124.14(9) . . ? C11 C12 C13 120.29(9) . . ? C11 C10 H10 119.7 . . ? C11 C10 C9 120.63(9) . . ? C9 C10 H10 119.7 . . ? C12 C11 H11 120.0 . . ? C10 C11 C12 119.97(9) . . ? C10 C11 H11 120.0 . . ? C6 C7 H7 119.7 . . ? C6 C7 C2 120.57(9) . . ? C2 C7 H7 119.7 . . ? C5 C6 H6 120.1 . . ? C7 C6 C5 119.81(9) . . ? C7 C6 H6 120.1 . . ? C5 C4 H4 120.0 . . ? C3 C4 C5 120.09(9) . . ? C3 C4 H4 120.0 . . ? C10 C9 C8 120.78(9) . . ? C14 C9 C10 118.50(9) . . ? C14 C9 C8 120.70(9) . . ? C9 C14 H14 119.2 . . ? C13 C14 C9 121.54(9) . . ? C13 C14 H14 119.2 . . ? C12 C13 H13 120.5 . . ? C14 C13 C12 119.05(9) . . ? C14 C13 H13 120.5 . . ? C4 C3 H3 120.0 . . ? C4 C3 C2 120.09(9) . . ? C2 C3 H3 120.0 . . ? C7 C2 C3 119.66(9) . . ? C7 C2 C1 118.60(9) . . ? C3 C2 C1 121.74(9) . . ? N1 C8 C9 121.23(9) . . ? N1 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? O1 C1 C2 115.59(9) . . ? O2 C1 O1 122.83(9) . . ? O2 C1 C2 121.57(9) . . ? O3 C15 H15A 109.5 . . ? O3 C15 H15B 109.5 . . ? O3 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? 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 O3 C12 1.3692(12) . ? O3 C15 1.4314(13) . ? O1 H1 0.8400 . ? O1 C1 1.3105(12) . ? O2 C1 1.2396(12) . ? N1 C5 1.4076(13) . ? N1 C8 1.2773(14) . ? C5 C6 1.4021(14) . ? C5 C4 1.4012(14) . ? C12 C11 1.3944(14) . ? C12 C13 1.3978(14) . ? C10 H10 0.9500 . ? C10 C11 1.3845(14) . ? C10 C9 1.4015(14) . ? C11 H11 0.9500 . ? C7 H7 0.9500 . ? C7 C6 1.3831(14) . ? C7 C2 1.3976(14) . ? C6 H6 0.9500 . ? C4 H4 0.9500 . ? C4 C3 1.3878(14) . ? C9 C14 1.3973(14) . ? C9 C8 1.4656(14) . ? C14 H14 0.9500 . ? C14 C13 1.3855(14) . ? C13 H13 0.9500 . ? C3 H3 0.9500 . ? C3 C2 1.3983(14) . ? C2 C1 1.4751(14) . ? C8 H8 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? 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 O3 C12 C11 C10 178.44(9) . . . . ? O3 C12 C13 C14 -178.78(9) . . . . ? N1 C5 C6 C7 177.24(9) . . . . ? N1 C5 C4 C3 -176.33(9) . . . . ? C5 N1 C8 C9 176.62(9) . . . . ? C5 C4 C3 C2 -0.28(15) . . . . ? C10 C9 C14 C13 -1.47(15) . . . . ? C10 C9 C8 N1 172.32(10) . . . . ? C11 C12 C13 C14 0.94(15) . . . . ? C11 C10 C9 C14 1.10(15) . . . . ? C11 C10 C9 C8 -177.45(9) . . . . ? C7 C2 C1 O1 -176.39(9) . . . . ? C7 C2 C1 O2 3.19(15) . . . . ? C6 C5 C4 C3 -0.51(15) . . . . ? C6 C7 C2 C3 0.41(15) . . . . ? C6 C7 C2 C1 179.92(9) . . . . ? C4 C5 C6 C7 1.25(15) . . . . ? C4 C3 C2 C7 0.33(15) . . . . ? C4 C3 C2 C1 -179.16(9) . . . . ? C9 C10 C11 C12 0.26(15) . . . . ? C9 C14 C13 C12 0.46(15) . . . . ? C14 C9 C8 N1 -6.21(15) . . . . ? C13 C12 C11 C10 -1.29(15) . . . . ? C3 C2 C1 O1 3.12(15) . . . . ? C3 C2 C1 O2 -177.31(10) . . . . ? C2 C7 C6 C5 -1.20(15) . . . . ? C8 N1 C5 C6 137.55(10) . . . . ? C8 N1 C5 C4 -46.56(14) . . . . ? C8 C9 C14 C13 177.08(9) . . . . ? C15 O3 C12 C11 -177.57(9) . . . . ? C15 O3 C12 C13 2.16(14) . . . . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -0.0824 -9.7101 -1.5961 -0.2287 -0.9550 -0.1888 2.4830 0.0169 -0.5500 -0.0333 -0.1504 0.9881 -2.4830 -0.0169 0.5500 0.0333 0.1504 -0.9881 -0.0142 9.7155 1.6185 0.2302 0.9615 0.1504 0.0796 1.1957 -13.6580 0.9722 -0.2324 0.0274 0.0339 -1.1270 13.6485 -0.9725 0.2323 0.0188 1.6177 0.1217 10.0473 -0.7284 0.1725 0.6631 2.2633 0.9345 4.9652 -0.3715 0.0866 0.9244 -1.7657 -0.2777 -9.2423 0.6722 -0.1589 -0.7231 0.0858 4.8665 11.8964 -0.6444 0.7534 0.1311 0.0614 -4.8040 -11.9858 0.6484 -0.7579 -0.0717