#------------------------------------------------------------------------------ #$Date: 2023-10-27 01:36:08 +0300 (Fri, 27 Oct 2023) $ #$Revision: 287127 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/75/7247584.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_7247584 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 H13 N O3' _chemical_formula_sum 'C15 H13 N O3' _chemical_formula_weight 255.26 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -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 109.0366(8) _cell_angle_beta 94.0110(8) _cell_angle_gamma 90.8565(8) _cell_formula_units_Z 2 _cell_length_a 3.89223(4) _cell_length_b 10.76523(10) _cell_length_c 15.40737(14) _cell_measurement_reflns_used 24606 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 78.5470 _cell_measurement_theta_min 4.3220 _cell_volume 608.291(11) _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 100.00(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 5.8140 _diffrn_detector_type 'Pilatus 300K' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.977 _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 -60.00 25.00 0.50 0.31 -- -49.71 38.00 0.00 170 2 \w -72.00 15.00 0.50 0.31 -- -49.71 77.00 0.00 174 3 \w -71.00 -11.00 0.50 0.44 -- -86.25 38.00-120.00 120 4 \w -92.00 -16.00 0.50 0.44 -- -86.25 125.00 -60.00 152 5 \w -97.00 -11.00 0.50 0.44 -- -86.25 19.00-180.00 172 6 \w -96.00 -15.00 0.50 0.44 -- -86.25 57.00 -60.00 162 7 \w -121.00 -35.00 0.50 0.31 -- -49.71 -57.00-150.00 172 8 \w 59.00 120.00 0.50 0.31 -- 49.71 178.00-120.00 122 9 \w 85.00 173.00 0.50 0.44 -- 107.75 77.00 -90.00 176 10 \w 98.00 178.00 0.50 0.44 -- 107.75 38.00 30.00 160 11 \w 98.00 178.00 0.50 0.44 -- 107.75 38.00 -30.00 160 12 \w 98.00 178.00 0.50 0.44 -- 107.75 38.00 -90.00 160 13 \w 85.00 173.00 0.50 0.44 -- 107.75 77.00 60.00 176 14 \w 91.00 178.00 0.50 0.44 -- 107.75 125.00 150.00 174 15 \w 98.00 178.00 0.50 0.44 -- 107.75 38.00 150.00 160 16 \w 93.00 178.00 0.50 0.44 -- 107.75 57.00 90.00 170 17 \w 85.00 173.00 0.50 0.44 -- 107.75 77.00 -60.00 176 18 \w 93.00 178.00 0.50 0.44 -- 107.75 57.00-180.00 170 19 \w 85.00 173.00 0.50 0.44 -- 107.75 77.00-180.00 176 20 \w 85.00 173.00 0.50 0.44 -- 107.75 77.00-150.00 176 21 \w 85.00 173.00 0.50 0.44 -- 107.75 77.00 0.00 176 22 \w 39.00 110.00 0.50 0.44 -- 107.75 -99.00-150.00 142 23 \w 33.00 71.00 0.50 0.44 -- 107.75 -38.00 -30.00 76 24 \w 37.00 96.00 0.50 0.44 -- 107.75 -57.00 30.00 118 25 \w 39.00 110.00 0.50 0.44 -- 107.75 -99.00 60.00 142 26 \w 38.00 117.00 0.50 0.44 -- 107.75-125.00 120.00 158 27 \w 39.00 110.00 0.50 0.44 -- 107.75 -99.00 150.00 142 28 \w 37.00 165.00 0.50 0.44 -- 107.75 0.00 60.00 256 29 \w 33.00 71.00 0.50 0.44 -- 107.75 -38.00 -60.00 76 30 \w 33.00 71.00 0.50 0.44 -- 107.75 -38.00 -90.00 76 31 \w 39.00 110.00 0.50 0.44 -- 107.75 -99.00 -60.00 142 32 \w 38.00 117.00 0.50 0.44 -- 107.75-125.00-150.00 158 33 \w 37.00 96.00 0.50 0.44 -- 107.75 -57.00 -60.00 118 34 \w 33.00 71.00 0.50 0.44 -- 107.75 -38.00-120.00 76 35 \w 37.00 165.00 0.50 0.44 -- 107.75 0.00 -60.00 256 36 \w 37.00 165.00 0.50 0.44 -- 107.75 0.00 30.00 256 37 \w 37.00 165.00 0.50 0.44 -- 107.75 0.00 -30.00 256 38 \w 37.00 165.00 0.50 0.44 -- 107.75 0.00 -90.00 256 39 \w 37.00 165.00 0.50 0.44 -- 107.75 0.00-120.00 256 40 \w 37.00 165.00 0.50 0.44 -- 107.75 0.00-150.00 256 41 \w 37.00 165.00 0.50 0.44 -- 107.75 0.00 0.00 256 42 \w 37.00 165.00 0.50 0.44 -- 107.75 0.00-180.00 256 43 \w 40.00 124.00 0.50 0.31 -- 49.71 38.00 -90.00 168 44 \w 37.00 165.00 0.50 0.44 -- 107.75 0.00 90.00 256 45 \w 37.00 165.00 0.50 0.44 -- 107.75 0.00 120.00 256 46 \w 27.00 115.00 0.50 0.31 -- 49.71 77.00-120.00 176 47 \w 27.00 115.00 0.50 0.31 -- 49.71 77.00 60.00 176 48 \w 27.00 115.00 0.50 0.31 -- 49.71 77.00 150.00 176 49 \w 27.00 115.00 0.50 0.31 -- 49.71 77.00 -30.00 176 50 \w 27.00 115.00 0.50 0.31 -- 49.71 77.00 30.00 176 51 \w 27.00 115.00 0.50 0.31 -- 49.71 77.00 120.00 176 52 \w -120.00 -70.00 0.50 0.31 -- -49.71-125.00 -61.00 100 53 \w -121.00 -35.00 0.50 0.31 -- -49.71 -57.00 -30.00 172 54 \w -124.00 -39.00 0.50 0.31 -- -49.71 -38.00 60.00 170 55 \w -121.00 -35.00 0.50 0.31 -- -49.71 -57.00 150.00 172 56 \w -124.00 -39.00 0.50 0.31 -- -49.71 -38.00 0.00 170 57 \w -121.00 -35.00 0.50 0.31 -- -49.71 -57.00 -90.00 172 58 \w -121.00 -35.00 0.50 0.31 -- -49.71 -57.00 -60.00 172 59 \w -125.00 -38.00 0.50 0.31 -- -49.71 -19.00-180.00 174 60 \w -151.00 -64.00 0.50 0.44 -- -86.25 -77.00-180.00 174 61 \w -151.00 -64.00 0.50 0.44 -- -86.25 -77.00 0.00 174 62 \w -124.00 -39.00 0.50 0.31 -- -49.71 -38.00 150.00 170 63 \w -157.00 -71.00 0.50 0.44 -- -86.25 -57.00 90.00 172 64 \w -151.00 -64.00 0.50 0.44 -- -86.25 -77.00 60.00 174 65 \w -157.00 -71.00 0.50 0.44 -- -86.25 -57.00 120.00 172 66 \w -151.00 -64.00 0.50 0.44 -- -86.25 -77.00 30.00 174 67 \w -157.00 -71.00 0.50 0.44 -- -86.25 -57.00 30.00 172 68 \w -151.00 -64.00 0.50 0.44 -- -86.25 -77.00 -90.00 174 69 \w -151.00 -64.00 0.50 0.44 -- -86.25 -77.00-150.00 174 70 \w -151.00 -64.00 0.50 0.44 -- -86.25 -77.00 -30.00 174 71 \w -151.00 -64.00 0.50 0.44 -- -86.25 -77.00 -60.00 174 72 \w -151.00 -64.00 0.50 0.44 -- -86.25 -77.00 120.00 174 73 \w -151.00 -64.00 0.50 0.44 -- -86.25 -77.00 150.00 174 74 \w -151.00 -64.00 0.50 0.44 -- -86.25 -77.00 90.00 174 75 \w -157.00 -71.00 0.50 0.44 -- -86.25 -57.00 150.00 172 76 \w -161.00 -75.00 0.50 0.44 -- -86.25 -19.00 120.00 172 77 \w -161.00 -76.00 0.50 0.44 -- -86.25 -38.00 120.00 170 78 \w -157.00 -71.00 0.50 0.44 -- -86.25 -57.00 -90.00 172 79 \w -151.00 -64.00 0.50 0.44 -- -86.25 -77.00-120.00 174 80 \w -157.00 -71.00 0.50 0.44 -- -86.25 -57.00-180.00 172 81 \w -161.00 -75.00 0.50 0.44 -- -86.25 -19.00-120.00 172 82 \w -161.00 -75.00 0.50 0.44 -- -86.25 -19.00-150.00 172 ; _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 -0.0636443000 _diffrn_orient_matrix_UB_12 0.0070630000 _diffrn_orient_matrix_UB_13 -0.0980682000 _diffrn_orient_matrix_UB_21 -0.1503870000 _diffrn_orient_matrix_UB_22 0.1367979000 _diffrn_orient_matrix_UB_23 0.0396238000 _diffrn_orient_matrix_UB_31 0.3619629000 _diffrn_orient_matrix_UB_32 0.0647345000 _diffrn_orient_matrix_UB_33 0.0084342000 _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 0.0391 _diffrn_reflns_av_unetI/netI 0.0139 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.977 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 33767 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.977 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 78.744 _diffrn_reflns_theta_min 4.348 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.803 _exptl_absorpt_correction_T_max 0.948 _exptl_absorpt_correction_T_min 0.880 _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 yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.394 _exptl_crystal_description prism _exptl_crystal_F_000 268 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.165 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.241 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.044 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 174 _refine_ls_number_reflns 2543 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.086 _refine_ls_R_factor_all 0.0353 _refine_ls_R_factor_gt 0.0337 _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^)+(0.0484P)^2^+0.1845P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0934 _refine_ls_wR_factor_ref 0.0944 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2383 _reflns_number_total 2543 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00758h2.cif _cod_data_source_block ps010 _cod_database_code 7247584 _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 0.939 _shelx_estimated_absorpt_t_min 0.837 _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: C3(H3), C7(H7), C6(H6), C13(H13), C4(H4), C11(H11), C8(H8), C14(H14), C10(H10) 2.b Idealised Me refined as rotating group: C15(H15A,H15B,H15C) 2.c Idealised tetrahedral OH refined as rotating group: O2(H2) ; _shelx_res_file ; TITL ps010_a.res in P-1 ps010.res created by SHELXL-2018/3 at 15:04:25 on 06-Dec-2022 REM Old TITL ps010 in P-1 REM SHELXT solution in P-1: R1 0.100, Rweak 0.003, Alpha 0.034 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C15 N O3 CELL 1.54184 3.892234 10.765225 15.407367 109.0366 94.011 90.8565 ZERR 2 0.000043 0.000096 0.000136 0.0008 0.0008 0.0008 LATT 1 SFAC C H N O UNIT 30 26 2 6 L.S. 10 PLAN 10 SIZE 0.08 0.165 0.23 TEMP -173 CONF BOND list 4 fmap 2 53 ACTA MORE -1 BOND $H REM REM REM WGHT 0.048400 0.184500 FVAR 0.84818 O3 4 1.263239 0.504889 0.915532 11.00000 0.02434 0.01781 = 0.01678 0.00456 -0.00255 0.00170 O1 4 0.251788 0.114312 0.076727 11.00000 0.03160 0.01985 = 0.01805 0.00737 -0.00196 -0.00397 O2 4 0.041652 -0.072725 0.090391 11.00000 0.03307 0.01777 = 0.01620 0.00403 -0.00281 -0.00471 AFIX 147 H2 2 -0.046004 -0.082673 0.037048 11.00000 -1.50000 AFIX 0 N1 3 0.758879 0.188368 0.495597 11.00000 0.01907 0.01901 = 0.01722 0.00578 0.00030 -0.00009 C9 1 0.877902 0.360161 0.641884 11.00000 0.01628 0.01790 = 0.01772 0.00619 0.00170 -0.00139 C3 1 0.565199 0.191475 0.256825 11.00000 0.01748 0.01664 = 0.01852 0.00660 0.00319 0.00201 AFIX 43 H3 2 0.609623 0.245023 0.220243 11.00000 -1.20000 AFIX 0 C12 1 1.127096 0.464027 0.826914 11.00000 0.01562 0.01870 = 0.01647 0.00652 0.00072 -0.00257 C2 1 0.369788 0.074149 0.218307 11.00000 0.01755 0.01598 = 0.01643 0.00400 0.00282 0.00363 C7 1 0.312378 -0.005653 0.271969 11.00000 0.02017 0.01407 = 0.01903 0.00399 0.00197 0.00064 AFIX 43 H7 2 0.183523 -0.086553 0.245667 11.00000 -1.20000 AFIX 0 C6 1 0.442255 0.032505 0.363299 11.00000 0.02183 0.01649 = 0.01959 0.00752 0.00265 0.00282 AFIX 43 H6 2 0.404658 -0.022718 0.399134 11.00000 -1.20000 AFIX 0 C13 1 1.190151 0.333556 0.775301 11.00000 0.01845 0.01693 = 0.02164 0.00864 0.00019 0.00085 AFIX 43 H13 2 1.317184 0.280258 0.803444 11.00000 -1.20000 AFIX 0 C4 1 0.694770 0.230338 0.348044 11.00000 0.01765 0.01559 = 0.01980 0.00469 0.00116 0.00011 AFIX 43 H4 2 0.828879 0.310112 0.373690 11.00000 -1.20000 AFIX 0 C11 1 0.938800 0.542393 0.786056 11.00000 0.01686 0.01507 = 0.01966 0.00555 0.00237 -0.00030 AFIX 43 H11 2 0.894663 0.630619 0.820562 11.00000 -1.20000 AFIX 0 C5 1 0.628716 0.152313 0.402758 11.00000 0.01650 0.01764 = 0.01736 0.00490 0.00153 0.00443 C8 1 0.735780 0.308163 0.546338 11.00000 0.01779 0.01907 = 0.01882 0.00774 0.00107 0.00108 AFIX 43 H8 2 0.619824 0.366314 0.520355 11.00000 -1.20000 AFIX 0 C14 1 1.068731 0.282723 0.684231 11.00000 0.01864 0.01485 = 0.02033 0.00528 0.00174 -0.00043 AFIX 43 H14 2 1.114066 0.194650 0.649658 11.00000 -1.20000 AFIX 0 C1 1 0.218287 0.040091 0.122355 11.00000 0.01888 0.01522 = 0.01759 0.00388 0.00347 0.00240 C15 1 1.199740 0.636684 0.971534 11.00000 0.02297 0.01832 = 0.01774 0.00357 0.00010 0.00089 AFIX 137 H15A 2 1.300340 0.699091 0.945254 11.00000 -1.50000 H15B 2 1.304847 0.653034 1.034131 11.00000 -1.50000 H15C 2 0.950679 0.647909 0.973454 11.00000 -1.50000 AFIX 0 C10 1 0.816730 0.489238 0.693967 11.00000 0.01721 0.01816 = 0.02000 0.00877 0.00084 0.00056 AFIX 43 H10 2 0.688405 0.542287 0.665874 11.00000 -1.20000 AFIX 0 HKLF 4 REM ps010_a.res in P-1 REM wR2 = 0.0944, GooF = S = 1.086, Restrained GooF = 1.086 for all data REM R1 = 0.0337 for 2383 Fo > 4sig(Fo) and 0.0353 for all 2543 data REM 174 parameters refined using 0 restraints END WGHT 0.0484 0.1846 REM Highest difference peak 0.241, deepest hole -0.225, 1-sigma level 0.044 Q1 1 1.1540 0.3979 0.7990 11.00000 0.05 0.24 Q2 1 0.6468 0.0757 0.3777 11.00000 0.05 0.24 Q3 1 0.2925 0.0610 0.1753 11.00000 0.05 0.22 Q4 1 0.8074 0.3328 0.6007 11.00000 0.05 0.21 Q5 1 0.8637 0.4240 0.6652 11.00000 0.05 0.20 Q6 1 0.9247 0.5168 0.7376 11.00000 0.05 0.19 Q7 1 1.0581 0.5032 0.8010 11.00000 0.05 0.18 Q8 1 0.6426 0.2033 0.2978 11.00000 0.05 0.18 Q9 1 0.8457 0.5020 0.7426 11.00000 0.05 0.18 Q10 1 0.5505 0.1042 0.2243 11.00000 0.05 0.18 ; _shelx_res_checksum 95589 _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 1.440 _oxdiff_exptl_absorpt_empirical_full_min 0.697 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 1.2632(2) 0.50489(7) 0.91553(5) 0.02012(18) Uani 1 1 d . . . . . O1 O 0.2518(2) 0.11431(7) 0.07673(5) 0.02314(19) Uani 1 1 d . . . . . O2 O 0.0417(2) -0.07272(7) 0.09039(5) 0.02302(19) Uani 1 1 d . . . . . H2 H -0.046004 -0.082673 0.037048 0.035 Uiso 1 1 calc R U . . . N1 N 0.7589(2) 0.18837(8) 0.49560(6) 0.0185(2) Uani 1 1 d . . . . . C9 C 0.8779(3) 0.36016(10) 0.64188(7) 0.0172(2) Uani 1 1 d . . . . . C3 C 0.5652(3) 0.19147(10) 0.25683(7) 0.0172(2) Uani 1 1 d . . . . . H3 H 0.609623 0.245023 0.220243 0.021 Uiso 1 1 calc R U . . . C12 C 1.1271(3) 0.46403(10) 0.82691(7) 0.0168(2) Uani 1 1 d . . . . . C2 C 0.3698(3) 0.07415(9) 0.21831(7) 0.0169(2) Uani 1 1 d . . . . . C7 C 0.3124(3) -0.00565(10) 0.27197(7) 0.0181(2) Uani 1 1 d . . . . . H7 H 0.183523 -0.086553 0.245667 0.022 Uiso 1 1 calc R U . . . C6 C 0.4423(3) 0.03251(10) 0.36330(7) 0.0188(2) Uani 1 1 d . . . . . H6 H 0.404658 -0.022718 0.399134 0.023 Uiso 1 1 calc R U . . . C13 C 1.1902(3) 0.33356(10) 0.77530(7) 0.0185(2) Uani 1 1 d . . . . . H13 H 1.317184 0.280258 0.803444 0.022 Uiso 1 1 calc R U . . . C4 C 0.6948(3) 0.23034(10) 0.34804(7) 0.0180(2) Uani 1 1 d . . . . . H4 H 0.828879 0.310112 0.373690 0.022 Uiso 1 1 calc R U . . . C11 C 0.9388(3) 0.54239(10) 0.78606(7) 0.0172(2) Uani 1 1 d . . . . . H11 H 0.894663 0.630619 0.820562 0.021 Uiso 1 1 calc R U . . . C5 C 0.6287(3) 0.15231(10) 0.40276(7) 0.0173(2) Uani 1 1 d . . . . . C8 C 0.7358(3) 0.30816(10) 0.54634(7) 0.0182(2) Uani 1 1 d . . . . . H8 H 0.619824 0.366314 0.520355 0.022 Uiso 1 1 calc R U . . . C14 C 1.0687(3) 0.28272(10) 0.68423(7) 0.0181(2) Uani 1 1 d . . . . . H14 H 1.114066 0.194650 0.649658 0.022 Uiso 1 1 calc R U . . . C1 C 0.2183(3) 0.04009(10) 0.12235(7) 0.0175(2) Uani 1 1 d . . . . . C15 C 1.1997(3) 0.63668(10) 0.97153(7) 0.0203(2) Uani 1 1 d . . . . . H15A H 1.300340 0.699091 0.945254 0.030 Uiso 1 1 calc R U . . . H15B H 1.304847 0.653034 1.034131 0.030 Uiso 1 1 calc R U . . . H15C H 0.950679 0.647909 0.973454 0.030 Uiso 1 1 calc R U . . . C10 C 0.8167(3) 0.48924(10) 0.69397(7) 0.0179(2) Uani 1 1 d . . . . . H10 H 0.688405 0.542287 0.665874 0.021 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 0.0243(4) 0.0178(4) 0.0168(3) 0.0046(3) -0.0025(3) 0.0017(3) O1 0.0316(4) 0.0199(4) 0.0181(4) 0.0074(3) -0.0020(3) -0.0040(3) O2 0.0331(5) 0.0178(4) 0.0162(3) 0.0040(3) -0.0028(3) -0.0047(3) N1 0.0191(5) 0.0190(4) 0.0172(4) 0.0058(3) 0.0003(3) -0.0001(3) C9 0.0163(5) 0.0179(5) 0.0177(5) 0.0062(4) 0.0017(4) -0.0014(4) C3 0.0175(5) 0.0166(5) 0.0185(5) 0.0066(4) 0.0032(4) 0.0020(4) C12 0.0156(5) 0.0187(5) 0.0165(5) 0.0065(4) 0.0007(4) -0.0026(4) C2 0.0176(5) 0.0160(5) 0.0164(5) 0.0040(4) 0.0028(4) 0.0036(4) C7 0.0202(5) 0.0141(4) 0.0190(5) 0.0040(4) 0.0020(4) 0.0006(4) C6 0.0218(5) 0.0165(5) 0.0196(5) 0.0075(4) 0.0027(4) 0.0028(4) C13 0.0184(5) 0.0169(5) 0.0216(5) 0.0086(4) 0.0002(4) 0.0009(4) C4 0.0177(5) 0.0156(5) 0.0198(5) 0.0047(4) 0.0012(4) 0.0001(4) C11 0.0169(5) 0.0151(4) 0.0197(5) 0.0056(4) 0.0024(4) -0.0003(4) C5 0.0165(5) 0.0176(5) 0.0174(5) 0.0049(4) 0.0015(4) 0.0044(4) C8 0.0178(5) 0.0191(5) 0.0188(5) 0.0077(4) 0.0011(4) 0.0011(4) C14 0.0186(5) 0.0148(5) 0.0203(5) 0.0053(4) 0.0017(4) -0.0004(4) C1 0.0189(5) 0.0152(4) 0.0176(5) 0.0039(4) 0.0035(4) 0.0024(4) C15 0.0230(5) 0.0183(5) 0.0177(5) 0.0036(4) 0.0001(4) 0.0009(4) C10 0.0172(5) 0.0182(5) 0.0200(5) 0.0088(4) 0.0008(4) 0.0006(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 -7 2 0.0737 -2 -1 1 0.0908 0 7 -2 0.0902 2 1 -1 0.1024 0 -3 -7 0.0402 0 3 7 0.0402 -2 -1 5 0.0771 2 3 1 0.0729 2 1 -6 0.0800 0 6 -6 0.0886 0 -7 6 0.0701 -1 4 -9 0.0842 2 5 -6 0.0819 0 1 9 0.0286 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 117.46(8) . . ? C1 O2 H2 109.5 . . ? C8 N1 C5 117.94(8) . . ? C14 C9 C8 121.94(9) . . ? C10 C9 C8 119.42(9) . . ? C10 C9 C14 118.62(9) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C4 C3 C2 120.38(9) . . ? O3 C12 C13 115.44(9) . . ? O3 C12 C11 124.48(9) . . ? C11 C12 C13 120.08(9) . . ? C3 C2 C7 119.47(9) . . ? C3 C2 C1 118.71(9) . . ? C7 C2 C1 121.78(9) . . ? C2 C7 H7 119.8 . . ? C6 C7 C2 120.43(9) . . ? C6 C7 H7 119.8 . . ? C7 C6 H6 120.0 . . ? C7 C6 C5 120.06(9) . . ? C5 C6 H6 120.0 . . ? C12 C13 H13 119.9 . . ? C14 C13 C12 120.26(9) . . ? C14 C13 H13 119.9 . . ? C3 C4 H4 119.9 . . ? C3 C4 C5 120.22(9) . . ? C5 C4 H4 119.9 . . ? C12 C11 H11 120.5 . . ? C10 C11 C12 118.91(9) . . ? C10 C11 H11 120.5 . . ? C6 C5 N1 118.85(9) . . ? C6 C5 C4 119.38(9) . . ? C4 C5 N1 121.70(9) . . ? N1 C8 C9 123.51(9) . . ? N1 C8 H8 118.2 . . ? C9 C8 H8 118.2 . . ? C9 C14 H14 119.8 . . ? C13 C14 C9 120.48(9) . . ? C13 C14 H14 119.8 . . ? O1 C1 O2 122.93(9) . . ? O1 C1 C2 121.82(9) . . ? O2 C1 C2 115.23(8) . . ? 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 . . ? C9 C10 H10 119.2 . . ? C11 C10 C9 121.66(9) . . ? C11 C10 H10 119.2 . . ? 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 1.3559(12) . ? O3 C15 1.4354(12) . ? O1 C1 1.2352(12) . ? O2 H2 0.8400 . ? O2 C1 1.3144(12) . ? N1 C5 1.4085(13) . ? N1 C8 1.2798(13) . ? C9 C8 1.4580(14) . ? C9 C14 1.4064(14) . ? C9 C10 1.3931(14) . ? C3 H3 0.9500 . ? C3 C2 1.3947(14) . ? C3 C4 1.3841(14) . ? C12 C13 1.4051(14) . ? C12 C11 1.3948(14) . ? C2 C7 1.3982(14) . ? C2 C1 1.4784(13) . ? C7 H7 0.9500 . ? C7 C6 1.3862(14) . ? C6 H6 0.9500 . ? C6 C5 1.3995(15) . ? C13 H13 0.9500 . ? C13 C14 1.3749(14) . ? C4 H4 0.9500 . ? C4 C5 1.4029(14) . ? C11 H11 0.9500 . ? C11 C10 1.3908(14) . ? C8 H8 0.9500 . ? C14 H14 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C10 H10 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 O3 C12 C13 C14 -178.92(9) . . . . ? O3 C12 C11 C10 179.11(9) . . . . ? C3 C2 C7 C6 1.32(15) . . . . ? C3 C2 C1 O1 -2.17(15) . . . . ? C3 C2 C1 O2 179.10(9) . . . . ? C3 C4 C5 N1 179.48(9) . . . . ? C3 C4 C5 C6 2.48(15) . . . . ? C12 C13 C14 C9 -0.52(16) . . . . ? C12 C11 C10 C9 0.01(15) . . . . ? C2 C3 C4 C5 -0.40(15) . . . . ? C2 C7 C6 C5 0.77(15) . . . . ? C7 C2 C1 O1 175.61(10) . . . . ? C7 C2 C1 O2 -3.12(14) . . . . ? C7 C6 C5 N1 -179.75(9) . . . . ? C7 C6 C5 C4 -2.66(15) . . . . ? C13 C12 C11 C10 -0.16(15) . . . . ? C4 C3 C2 C7 -1.50(15) . . . . ? C4 C3 C2 C1 176.33(9) . . . . ? C11 C12 C13 C14 0.42(16) . . . . ? C5 N1 C8 C9 -176.29(9) . . . . ? C8 N1 C5 C6 -138.35(10) . . . . ? C8 N1 C5 C4 44.63(14) . . . . ? C8 C9 C14 C13 -177.98(9) . . . . ? C8 C9 C10 C11 178.28(9) . . . . ? C14 C9 C8 N1 3.37(16) . . . . ? C14 C9 C10 C11 -0.11(15) . . . . ? C1 C2 C7 C6 -176.44(9) . . . . ? C15 O3 C12 C13 -178.78(9) . . . . ? C15 O3 C12 C11 1.92(14) . . . . ? C10 C9 C8 N1 -174.97(10) . . . . ? C10 C9 C14 C13 0.37(15) . . . . ? 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 -0.0936 -6.8800 1.6747 -0.2069 -0.8607 -0.4651 -2.4737 -1.2924 0.9667 0.0535 0.2335 -0.9709 -0.3801 6.8271 -1.5363 0.2231 0.9302 0.2914 2.4872 1.0936 -0.8799 -0.0643 -0.2593 0.9637 0.0111 -2.7341 -7.3957 0.7053 -0.6687 -0.2354 -0.0111 2.7341 7.3957 -0.7053 0.6687 0.2354 -2.2093 -1.2431 5.4397 -0.4016 0.3777 -0.8343 1.9477 3.4352 1.4943 -0.2462 0.2362 0.9400 2.1459 0.9945 -5.8564 0.4448 -0.4187 0.7917 -0.3993 6.4997 -6.1093 0.6704 0.7071 0.2247 -0.1194 -6.6581 5.9557 -0.6235 -0.6569 -0.4240 -0.7680 3.8163 -8.9462 0.9532 0.2831 -0.1064 1.5584 4.7442 -6.2838 0.5506 0.1656 0.8182 0.0321 1.2926 8.6458 -0.8408 0.5146 0.1682