#------------------------------------------------------------------------------ #$Date: 2023-10-27 01:36:08 +0300 (Fri, 27 Oct 2023) $ #$Revision: 287127 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/75/7247579.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_7247579 loop_ _publ_author_name 'Sobczak, Paulina' 'Siera\'nski, Tomasz' 'Swiatkowski, Marcin' 'Trzesowska-Kruszynska, Agata' _publ_section_title ; New Schiff base salts as sources of blue and green light in the solid state: the role of anion and protonation ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D3CE00758H _journal_year 2023 _chemical_formula_moiety 'C15 H14 N O3, N O3' _chemical_formula_sum 'C15 H14 N2 O6' _chemical_formula_weight 318.28 _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 geom _atom_sites_solution_primary dual _audit_creation_date 2023-01-05 _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 95.964(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.83768(17) _cell_length_b 14.8178(5) _cell_length_c 20.0275(6) _cell_measurement_reflns_used 7177 _cell_measurement_temperature 99.9(8) _cell_measurement_theta_max 78.1810 _cell_measurement_theta_min 3.6500 _cell_volume 1427.88(8) _computing_cell_refinement 'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)' _computing_data_collection 'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)' _computing_data_reduction 'CrysAlisPro 1.171.42.79a (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 (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 99.9(8) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 5.8140 _diffrn_detector_type 'Pilatus 300K' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.923 _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 -20.00 27.00 0.50 20.00 -- -48.87 19.00-180.00 94 2 \w -20.00 27.00 0.50 20.00 -- -48.87 19.00-150.00 94 3 \w -20.00 27.00 0.50 20.00 -- -48.87 19.00 60.00 94 4 \w -20.00 27.00 0.50 20.00 -- -48.87 19.00 150.00 94 5 \w -27.00 20.00 0.50 20.00 -- 48.87 -19.00 0.00 94 6 \w -27.00 20.00 0.50 20.00 -- 48.87 -19.00 -90.00 94 7 \w -41.00 -13.00 0.50 80.00 -- -88.50 38.00 -30.00 56 8 \w -84.00 -20.00 0.50 80.00 -- -88.50 113.00 31.00 128 9 \w -66.00 -17.00 0.50 80.00 -- -88.50 57.00 120.00 98 10 \w -87.00 -19.00 0.50 80.00 -- -88.50 125.00 60.00 136 11 \w -66.00 -17.00 0.50 80.00 -- -88.50 57.00 30.00 98 12 \w -87.00 -19.00 0.50 80.00 -- -88.50 125.00 90.00 136 13 \w -41.00 -13.00 0.50 80.00 -- -88.50 38.00-120.00 56 14 \w -41.00 -13.00 0.50 80.00 -- -88.50 38.00 0.00 56 15 \w -66.00 -17.00 0.50 80.00 -- -88.50 57.00 60.00 98 16 \w 41.00 106.00 0.50 80.00 -- 110.00 -99.00 90.00 130 17 \w 38.00 66.00 0.50 80.00 -- 110.00 -57.00-120.00 56 18 \w 94.00 178.00 0.50 80.00 -- 110.00 57.00 60.00 168 19 \w 38.00 66.00 0.50 80.00 -- 110.00 -57.00 150.00 56 20 \w 94.00 178.00 0.50 80.00 -- 110.00 125.00 120.00 168 21 \w 38.00 66.00 0.50 80.00 -- 110.00 -57.00 30.00 56 22 \w 94.00 178.00 0.50 80.00 -- 110.00 57.00 -60.00 168 23 \w 25.00 114.00 0.50 20.00 -- 48.87 77.00-120.00 178 24 \w 25.00 88.00 0.50 20.00 -- 48.87 77.00 150.00 126 25 \w 25.00 114.00 0.50 20.00 -- 48.87 77.00 30.00 178 ; _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 -0.0458447000 _diffrn_orient_matrix_UB_12 0.0199091000 _diffrn_orient_matrix_UB_13 0.0735447000 _diffrn_orient_matrix_UB_21 -0.0799950000 _diffrn_orient_matrix_UB_22 0.0979285000 _diffrn_orient_matrix_UB_23 -0.0192161000 _diffrn_orient_matrix_UB_31 -0.3066855000 _diffrn_orient_matrix_UB_32 -0.0285445000 _diffrn_orient_matrix_UB_33 -0.0143537000 _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 0.0791 _diffrn_reflns_av_unetI/netI 0.0131 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.923 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 3740 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.923 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 79.444 _diffrn_reflns_theta_min 3.718 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.988 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_correction_T_min 0.922 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.79a (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 yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.481 _exptl_crystal_description block _exptl_crystal_F_000 664 _exptl_crystal_size_max 0.137 _exptl_crystal_size_mid 0.044 _exptl_crystal_size_min 0.021 _refine_diff_density_max 0.385 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.078 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 211 _refine_ls_number_reflns 3740 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.092 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0568 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1081P)^2^+0.7391P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1666 _refine_ls_wR_factor_ref 0.1731 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3222 _reflns_number_total 3740 _reflns_threshold_expression 'I > 2\s(I)' _twin_special_details ; Component 2 rotated by 179.9930\% around [-0.00 0.00 1.00] (reciprocal) or [0.39 -0.00 0.92] (direct) ; _cod_data_source_file d3ce00758h2.cif _cod_data_source_block ps20_zolte2_twin1_hklf4 _cod_original_cell_volume 1427.87(9) _cod_database_code 7247579 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C15 H14 N2 O6 ' _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 0.980 _shelx_estimated_absorpt_t_min 0.876 _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.764(2) 0.236(2) 2. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 3.a Aromatic/amide H refined with riding coordinates: N1(H1A), C6(H6), C14(H14), C13(H13), C3(H3), C4(H4), C7(H7), C8(H8), C10(H10), C11(H11) 3.b Idealised Me refined as rotating group: C15(H15A,H15B,H15C) 3.c Idealised tetrahedral OH refined as rotating group: O1(H1) ; _shelx_res_file ; TITL ps20_zolte2_twin1_hklf4_a.res in P2(1)/n ps20_zolte2_twin1_hklf4.res created by SHELXL-2018/3 at 13:29:44 on 05-Jan-2023 REM Old TITL ps20_zolte2_twin1_hklf4 in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.174, Rweak 0.006, Alpha 0.029 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C15 N3 O5 CELL 1.54184 4.837677 14.817764 20.027458 90 95.9644 90 ZERR 4 0.000167 0.000532 0.000642 0 0.0033 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O UNIT 60 56 8 24 L.S. 10 PLAN 20 SIZE 0.021 0.044 0.137 TEMP -173 CONF BOND list 4 MORE -1 BOND $H fmap 2 acta REM REM REM WGHT 0.108100 0.739100 BASF 0.23600 FVAR 1.53836 O4 4 0.671254 0.559569 0.362900 11.00000 0.04715 0.02586 = 0.02973 0.00047 -0.00421 0.00082 O2 4 -0.345056 0.545305 0.071499 11.00000 0.02822 0.03200 = 0.03186 0.00412 -0.00359 0.00476 O1 4 -0.239758 0.418758 0.018036 11.00000 0.02871 0.04530 = 0.02600 -0.00363 -0.00729 0.00388 AFIX 147 H1 2 -0.387715 0.431425 -0.005872 11.00000 -1.50000 AFIX 0 O3 4 1.698086 0.282452 0.482485 11.00000 0.03809 0.04006 = 0.02738 -0.00069 -0.01091 0.00612 O5 4 0.623800 0.704449 0.357437 11.00000 0.05115 0.02647 = 0.05528 -0.00144 0.01767 0.00374 O6 4 0.815950 0.634499 0.280171 11.00000 0.06277 0.04365 = 0.03470 -0.00362 0.01684 -0.00065 N2 3 0.704506 0.633793 0.333822 11.00000 0.02943 0.02679 = 0.03057 -0.00255 -0.00186 0.00109 N1 3 0.666205 0.411012 0.274153 11.00000 0.02668 0.02678 = 0.02229 -0.00044 -0.00109 -0.00159 AFIX 43 H1A 2 0.704149 0.457170 0.301208 11.00000 -1.20000 AFIX 0 C6 1 0.277319 0.497181 0.225568 11.00000 0.02771 0.03052 = 0.02247 -0.00011 0.00001 -0.00294 AFIX 43 H6 2 0.305233 0.536688 0.263020 11.00000 -1.20000 AFIX 0 C9 1 1.038511 0.329563 0.338169 11.00000 0.02776 0.03022 = 0.02244 0.00116 0.00026 0.00074 C1 1 -0.202199 0.474946 0.066592 11.00000 0.02314 0.02633 = 0.02245 0.00134 0.00088 -0.00245 C14 1 1.148078 0.401586 0.378098 11.00000 0.03052 0.02667 = 0.02591 0.00102 0.00112 0.00293 AFIX 43 H14 2 1.069769 0.460103 0.371474 11.00000 -1.20000 AFIX 0 C5 1 0.449353 0.422800 0.220956 11.00000 0.02341 0.02966 = 0.02182 0.00422 -0.00218 -0.00314 C13 1 1.368320 0.388576 0.426922 11.00000 0.03080 0.03465 = 0.02341 -0.00202 -0.00038 -0.00058 AFIX 43 H13 2 1.441443 0.437896 0.453453 11.00000 -1.20000 AFIX 0 C3 1 0.197367 0.380462 0.115862 11.00000 0.02772 0.02781 = 0.02430 0.00066 -0.00216 -0.00143 AFIX 43 H3 2 0.167983 0.340768 0.078549 11.00000 -1.20000 AFIX 0 C4 1 0.412441 0.363663 0.166389 11.00000 0.02699 0.02739 = 0.02774 0.00255 -0.00032 0.00124 AFIX 43 H4 2 0.531316 0.313044 0.163730 11.00000 -1.20000 AFIX 0 C7 1 0.065522 0.513176 0.175266 11.00000 0.02615 0.02766 = 0.02391 0.00292 0.00062 0.00048 AFIX 43 H7 2 -0.053698 0.563662 0.178145 11.00000 -1.20000 AFIX 0 C8 1 0.813029 0.338142 0.286292 11.00000 0.02880 0.02858 = 0.02471 0.00093 0.00041 -0.00078 AFIX 43 H8 2 0.767323 0.286974 0.258758 11.00000 -1.20000 AFIX 0 C10 1 1.159382 0.243581 0.348806 11.00000 0.03971 0.02861 = 0.03034 -0.00201 -0.00749 0.00135 AFIX 43 H10 2 1.089952 0.194219 0.321803 11.00000 -1.20000 AFIX 0 C2 1 0.026498 0.455008 0.120041 11.00000 0.02169 0.02903 = 0.02314 0.00197 -0.00029 -0.00360 C12 1 1.482778 0.302361 0.437007 11.00000 0.02871 0.03631 = 0.02139 0.00155 -0.00159 0.00225 C15 1 1.812027 0.352063 0.526980 11.00000 0.03532 0.04934 = 0.02533 -0.00248 -0.00558 -0.00286 AFIX 137 H15A 2 1.857970 0.404769 0.500712 11.00000 -1.50000 H15B 2 1.980670 0.329710 0.553108 11.00000 -1.50000 H15C 2 1.675245 0.369243 0.557503 11.00000 -1.50000 AFIX 0 C11 1 1.376036 0.230217 0.397651 11.00000 0.04527 0.02836 = 0.03273 0.00093 -0.00696 0.00825 AFIX 43 H11 2 1.453614 0.171665 0.404698 11.00000 -1.20000 AFIX 0 HKLF 5 REM ps20_zolte2_twin1_hklf4_a.res in P2(1)/n REM wR2 = 0.1731, GooF = S = 1.092, Restrained GooF = 1.092 for all data REM R1 = 0.0568 for 3222 Fo > 4sig(Fo) and 0.0649 for all 3740 data REM 211 parameters refined using 0 restraints END WGHT 0.1081 0.7391 REM Highest difference peak 0.385, deepest hole -0.308, 1-sigma level 0.078 Q1 1 0.8653 0.4016 0.2881 11.00000 0.05 0.38 Q2 1 0.3089 0.4445 0.2222 11.00000 0.05 0.36 Q3 1 -0.4948 0.5531 0.0539 11.00000 0.05 0.35 Q4 1 0.0472 0.4037 0.1200 11.00000 0.05 0.35 Q5 1 1.5157 0.3545 0.4327 11.00000 0.05 0.33 Q6 1 1.8654 0.2780 0.5042 11.00000 0.05 0.33 Q7 1 0.5001 0.6453 0.3320 11.00000 0.05 0.31 Q8 1 0.4251 0.4941 0.2249 11.00000 0.05 0.31 Q9 1 1.3917 0.3443 0.4321 11.00000 0.05 0.30 Q10 1 0.4592 0.7028 0.3209 11.00000 0.05 0.29 Q11 1 -0.1570 0.5354 0.0725 11.00000 0.05 0.29 Q12 1 0.6781 0.3549 0.2762 11.00000 0.05 0.28 Q13 1 0.4908 0.5679 0.3447 11.00000 0.05 0.28 Q14 1 1.7158 0.3428 0.4883 11.00000 0.05 0.27 Q15 1 0.8629 0.5640 0.3595 11.00000 0.05 0.27 Q16 1 1.1117 0.3680 0.3473 11.00000 0.05 0.27 Q17 1 1.7987 0.2268 0.4878 11.00000 0.05 0.26 Q18 1 0.8563 0.5973 0.3655 11.00000 0.05 0.26 Q19 1 0.8229 0.6815 0.3577 11.00000 0.05 0.25 Q20 1 1.1130 0.2952 0.3424 11.00000 0.05 0.25 ; _shelx_res_checksum 33035 _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 1.934 _oxdiff_exptl_absorpt_empirical_full_min 0.695 _oxdiff_twin_integration_method simultaneous _oxdiff_twin_items 2 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 O4 O 0.6713(4) 0.55957(13) 0.36290(10) 0.0348(5) Uani 1 1 d . . . . . O2 O -0.3451(3) 0.54531(13) 0.07150(10) 0.0312(4) Uani 1 1 d . . . . . O1 O -0.2398(4) 0.41876(15) 0.01804(10) 0.0340(5) Uani 1 1 d . . . . . H1 H -0.387715 0.431425 -0.005872 0.051 Uiso 1 1 calc R U . . . O3 O 1.6981(4) 0.28245(15) 0.48249(10) 0.0362(5) Uani 1 1 d . . . . . O5 O 0.6238(4) 0.70445(14) 0.35744(13) 0.0434(5) Uani 1 1 d . . . . . O6 O 0.8160(5) 0.63450(16) 0.28017(11) 0.0462(6) Uani 1 1 d . . . . . N2 N 0.7045(4) 0.63379(15) 0.33382(12) 0.0293(5) Uani 1 1 d . . . . . N1 N 0.6662(4) 0.41101(15) 0.27415(11) 0.0255(5) Uani 1 1 d . . . . . H1A H 0.704149 0.457170 0.301208 0.031 Uiso 1 1 calc R U . . . C6 C 0.2773(5) 0.49718(18) 0.22557(13) 0.0271(5) Uani 1 1 d . . . . . H6 H 0.305233 0.536688 0.263020 0.032 Uiso 1 1 calc R U . . . C9 C 1.0385(5) 0.32956(19) 0.33817(13) 0.0270(5) Uani 1 1 d . . . . . C1 C -0.2022(5) 0.47495(17) 0.06659(12) 0.0241(5) Uani 1 1 d . . . . . C14 C 1.1481(5) 0.40159(19) 0.37810(13) 0.0278(5) Uani 1 1 d . . . . . H14 H 1.069769 0.460103 0.371474 0.033 Uiso 1 1 calc R U . . . C5 C 0.4494(5) 0.42280(18) 0.22096(13) 0.0253(5) Uani 1 1 d . . . . . C13 C 1.3683(5) 0.3886(2) 0.42692(13) 0.0298(6) Uani 1 1 d . . . . . H13 H 1.441443 0.437896 0.453453 0.036 Uiso 1 1 calc R U . . . C3 C 0.1974(5) 0.38046(18) 0.11586(13) 0.0270(5) Uani 1 1 d . . . . . H3 H 0.167983 0.340768 0.078549 0.032 Uiso 1 1 calc R U . . . C4 C 0.4124(5) 0.36366(18) 0.16639(14) 0.0276(5) Uani 1 1 d . . . . . H4 H 0.531316 0.313044 0.163730 0.033 Uiso 1 1 calc R U . . . C7 C 0.0655(5) 0.51318(18) 0.17527(13) 0.0260(5) Uani 1 1 d . . . . . H7 H -0.053698 0.563662 0.178145 0.031 Uiso 1 1 calc R U . . . C8 C 0.8130(5) 0.33814(19) 0.28629(13) 0.0275(5) Uani 1 1 d . . . . . H8 H 0.767323 0.286974 0.258758 0.033 Uiso 1 1 calc R U . . . C10 C 1.1594(6) 0.24358(19) 0.34881(15) 0.0337(6) Uani 1 1 d . . . . . H10 H 1.089952 0.194219 0.321803 0.040 Uiso 1 1 calc R U . . . C2 C 0.0265(5) 0.45501(17) 0.12004(13) 0.0248(5) Uani 1 1 d . . . . . C12 C 1.4828(5) 0.30236(19) 0.43701(13) 0.0291(6) Uani 1 1 d . . . . . C15 C 1.8120(6) 0.3521(2) 0.52698(15) 0.0373(7) Uani 1 1 d . . . . . H15A H 1.857970 0.404769 0.500712 0.056 Uiso 1 1 calc R U . . . H15B H 1.980670 0.329710 0.553108 0.056 Uiso 1 1 calc R U . . . H15C H 1.675245 0.369243 0.557503 0.056 Uiso 1 1 calc R U . . . C11 C 1.3760(6) 0.2302(2) 0.39765(15) 0.0362(6) Uani 1 1 d . . . . . H11 H 1.453614 0.171665 0.404698 0.043 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 O4 0.0471(11) 0.0259(10) 0.0297(10) 0.0005(8) -0.0042(8) 0.0008(8) O2 0.0282(9) 0.0320(10) 0.0319(10) 0.0041(8) -0.0036(7) 0.0048(7) O1 0.0287(9) 0.0453(12) 0.0260(10) -0.0036(8) -0.0073(7) 0.0039(8) O3 0.0381(10) 0.0401(12) 0.0274(10) -0.0007(8) -0.0109(8) 0.0061(8) O5 0.0511(12) 0.0265(11) 0.0553(14) -0.0014(10) 0.0177(10) 0.0037(8) O6 0.0628(14) 0.0437(13) 0.0347(12) -0.0036(10) 0.0168(10) -0.0007(10) N2 0.0294(11) 0.0268(12) 0.0306(12) -0.0025(9) -0.0019(9) 0.0011(8) N1 0.0267(10) 0.0268(11) 0.0223(10) -0.0004(9) -0.0011(8) -0.0016(8) C6 0.0277(12) 0.0305(14) 0.0225(12) -0.0001(10) 0.0000(9) -0.0029(9) C9 0.0278(12) 0.0302(14) 0.0224(12) 0.0012(10) 0.0003(10) 0.0007(9) C1 0.0231(11) 0.0263(13) 0.0224(11) 0.0013(10) 0.0009(9) -0.0025(9) C14 0.0305(12) 0.0267(13) 0.0259(12) 0.0010(10) 0.0011(10) 0.0029(9) C5 0.0234(11) 0.0297(13) 0.0218(12) 0.0042(10) -0.0022(9) -0.0031(9) C13 0.0308(13) 0.0347(15) 0.0234(12) -0.0020(10) -0.0004(10) -0.0006(10) C3 0.0277(12) 0.0278(14) 0.0243(12) 0.0007(10) -0.0022(10) -0.0014(9) C4 0.0270(12) 0.0274(13) 0.0277(13) 0.0025(10) -0.0003(10) 0.0012(9) C7 0.0261(11) 0.0277(13) 0.0239(12) 0.0029(10) 0.0006(9) 0.0005(9) C8 0.0288(12) 0.0286(13) 0.0247(12) 0.0009(10) 0.0004(10) -0.0008(9) C10 0.0397(14) 0.0286(14) 0.0303(14) -0.0020(11) -0.0075(11) 0.0014(11) C2 0.0217(11) 0.0290(13) 0.0231(12) 0.0020(10) -0.0003(9) -0.0036(9) C12 0.0287(12) 0.0363(15) 0.0214(12) 0.0015(10) -0.0016(10) 0.0022(10) C15 0.0353(14) 0.0493(18) 0.0253(13) -0.0025(12) -0.0056(11) -0.0029(12) C11 0.0453(15) 0.0284(14) 0.0327(14) 0.0009(12) -0.0070(12) 0.0082(11) 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 1 0.0175 -3 2 -1 0.0718 0 2 -13 0.0095 0 -2 13 0.0105 3 -1 0 0.0599 0 -10 1 0.0247 0 8 8 0.0141 0 -7 -9 0.0187 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 C1 O1 H1 109.5 . . ? C12 O3 C15 118.9(2) . . ? O5 N2 O4 120.2(2) . . ? O5 N2 O6 120.4(2) . . ? O6 N2 O4 119.4(2) . . ? C5 N1 H1A 117.1 . . ? C8 N1 H1A 117.1 . . ? C8 N1 C5 125.9(2) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? C7 C6 C5 119.5(2) . . ? C14 C9 C8 124.0(2) . . ? C14 C9 C10 118.4(2) . . ? C10 C9 C8 117.6(2) . . ? O2 C1 O1 124.2(2) . . ? O2 C1 C2 118.8(2) . . ? O1 C1 C2 117.0(2) . . ? C9 C14 H14 119.5 . . ? C13 C14 C9 121.0(3) . . ? C13 C14 H14 119.5 . . ? C6 C5 N1 116.5(2) . . ? C6 C5 C4 121.4(2) . . ? C4 C5 N1 122.1(2) . . ? C14 C13 H13 120.2 . . ? C14 C13 C12 119.6(3) . . ? C12 C13 H13 120.2 . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C2 C3 C4 120.1(2) . . ? C5 C4 H4 120.7 . . ? C3 C4 C5 118.7(2) . . ? C3 C4 H4 120.7 . . ? C6 C7 H7 120.0 . . ? C6 C7 C2 120.0(2) . . ? C2 C7 H7 120.0 . . ? N1 C8 C9 124.7(2) . . ? N1 C8 H8 117.7 . . ? C9 C8 H8 117.7 . . ? C9 C10 H10 119.6 . . ? C11 C10 C9 120.8(3) . . ? C11 C10 H10 119.6 . . ? C3 C2 C1 121.2(2) . . ? C3 C2 C7 120.4(2) . . ? C7 C2 C1 118.4(2) . . ? O3 C12 C13 124.5(2) . . ? O3 C12 C11 115.5(2) . . ? C11 C12 C13 120.0(2) . . ? 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 . . ? C10 C11 C12 120.2(3) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? 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 O4 N2 1.263(3) . ? O2 C1 1.260(3) . ? O1 H1 0.8400 . ? O1 C1 1.279(3) . ? O3 C12 1.343(3) . ? O3 C15 1.435(4) . ? O5 N2 1.229(3) . ? O6 N2 1.251(3) . ? N1 H1A 0.8800 . ? N1 C5 1.426(3) . ? N1 C8 1.301(3) . ? C6 H6 0.9500 . ? C6 C5 1.390(4) . ? C6 C7 1.381(4) . ? C9 C14 1.404(4) . ? C9 C8 1.432(4) . ? C9 C10 1.409(4) . ? C1 C2 1.487(3) . ? C14 H14 0.9500 . ? C14 C13 1.383(4) . ? C5 C4 1.398(4) . ? C13 H13 0.9500 . ? C13 C12 1.399(4) . ? C3 H3 0.9500 . ? C3 C4 1.396(4) . ? C3 C2 1.387(4) . ? C4 H4 0.9500 . ? C7 H7 0.9500 . ? C7 C2 1.399(4) . ? C8 H8 0.9500 . ? C10 H10 0.9500 . ? C10 C11 1.372(4) . ? C12 C11 1.395(4) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C11 H11 0.9500 . ? 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 O2 C1 C2 C3 -177.4(2) . . . . ? O2 C1 C2 C7 2.9(3) . . . . ? O1 C1 C2 C3 2.3(3) . . . . ? O1 C1 C2 C7 -177.4(2) . . . . ? O3 C12 C11 C10 -178.8(3) . . . . ? N1 C5 C4 C3 -179.2(2) . . . . ? C6 C5 C4 C3 0.0(4) . . . . ? C6 C7 C2 C1 -179.4(2) . . . . ? C6 C7 C2 C3 0.8(4) . . . . ? C9 C14 C13 C12 -0.4(4) . . . . ? C9 C10 C11 C12 -1.0(5) . . . . ? C14 C9 C8 N1 -6.8(4) . . . . ? C14 C9 C10 C11 1.0(4) . . . . ? C14 C13 C12 O3 179.3(2) . . . . ? C14 C13 C12 C11 0.4(4) . . . . ? C5 N1 C8 C9 176.9(2) . . . . ? C5 C6 C7 C2 -0.4(4) . . . . ? C13 C12 C11 C10 0.2(4) . . . . ? C4 C3 C2 C1 179.4(2) . . . . ? C4 C3 C2 C7 -0.9(4) . . . . ? C7 C6 C5 N1 179.2(2) . . . . ? C7 C6 C5 C4 0.0(4) . . . . ? C8 N1 C5 C6 165.8(2) . . . . ? C8 N1 C5 C4 -15.1(4) . . . . ? C8 C9 C14 C13 -179.3(2) . . . . ? C8 C9 C10 C11 -179.9(3) . . . . ? C10 C9 C14 C13 -0.3(4) . . . . ? C10 C9 C8 N1 174.1(3) . . . . ? C2 C3 C4 C5 0.5(4) . . . . ? C15 O3 C12 C13 3.8(4) . . . . ? C15 O3 C12 C11 -177.3(3) . . . . ? loop_ _twin_individual_id _twin_individual_mass_fraction_refined _oxdiff_twin_reflns_isolated _oxdiff_twin_reflns_overlapped _twin_individual_twin_lattice_type _twin_individual_twin_matrix_11 _twin_individual_twin_matrix_12 _twin_individual_twin_matrix_13 _twin_individual_twin_matrix_21 _twin_individual_twin_matrix_22 _twin_individual_twin_matrix_23 _twin_individual_twin_matrix_31 _twin_individual_twin_matrix_32 _twin_individual_twin_matrix_33 1 0.764(2) 6603 7686 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000 1.0000 2 0.236(2) 0 7686 nmt -0.9997 0.0004 -0.0000 0.0013 -1.0005 0.0008 0.8578 -0.0006 0.9997 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 0.3541 9.5460 0.5607 0.2151 0.8957 -0.3891 -3.0370 1.7474 -0.9852 0.1016 0.4330 0.8957 0.1155 1.9723 -12.6906 -0.8994 0.4278 0.0904 -0.1424 -1.9979 12.6902 0.9000 -0.4281 -0.0815 3.0951 -1.3694 -0.1764 -0.1821 -0.3783 -0.9076 -0.3725 -9.5438 0.7287 -0.1193 -0.9188 0.3762 0.0450 7.7601 7.6316 0.7137 0.6097 -0.3448 -0.2525 -6.5250 -9.3435 -0.8055 -0.4392 0.3978