#------------------------------------------------------------------------------ #$Date: 2019-11-17 08:09:22 +0200 (Sun, 17 Nov 2019) $ #$Revision: 228813 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/90/1549080.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_1549080 loop_ _publ_author_name 'Mu, Yingxiao' 'Yang, Zhiyong' 'Chen, Junru' 'Yang, Zhan' 'Li, Wenlang' 'Tan, Xianbao' 'Mao, Zhu' 'Yu, Tao' 'Zhao, Juan' 'Zheng, Shizhao' 'Liu, Siwei' 'Zhang, Yi' 'Chi, Zhenguo' 'Xu, Jiarui' 'Aldred, Matthew P.' _publ_section_title ; Mechano-induced persistent room-temperature phosphorescence from purely organic molecules. ; _journal_issue 15 _journal_name_full 'Chemical science' _journal_page_first 3782 _journal_page_last 3787 _journal_paper_doi 10.1039/c8sc00429c _journal_volume 9 _journal_year 2018 _chemical_formula_moiety 'C25 H15 N O2' _chemical_formula_sum 'C25 H15 N O2' _chemical_formula_weight 361.38 _chemical_name_systematic CX11 _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' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2017-10-20 _audit_creation_method ; Olex2 1.2 (compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5324) ; _audit_update_record ; 2017-10-20 deposited with the CCDC. 2018-03-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 114.831(7) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.4892(8) _cell_length_b 7.8471(4) _cell_length_c 15.5804(9) _cell_measurement_reflns_used 1454 _cell_measurement_temperature 153(7) _cell_measurement_theta_max 61.1650 _cell_measurement_theta_min 5.2640 _cell_volume 1718.65(19) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 153(7) _diffrn_detector_area_resol_mean 16.0855 _diffrn_measured_fraction_theta_full 0.9663 _diffrn_measured_fraction_theta_max 0.949 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -5.00 101.00 1.0000 26.0000 omega____ theta____ kappa____ phi______ frames - 34.3979 19.0000 -90.0000 106 #__ type_ start__ end____ width___ exp.time_ 2 omega 21.00 103.00 1.0000 26.0000 omega____ theta____ kappa____ phi______ frames - 34.3979 57.0000 -30.0000 82 #__ type_ start__ end____ width___ exp.time_ 3 omega 17.00 83.00 1.0000 104.0000 omega____ theta____ kappa____ phi______ frames - 88.6885 -94.0000 -150.0000 66 #__ type_ start__ end____ width___ exp.time_ 4 omega 21.00 66.00 1.0000 104.0000 omega____ theta____ kappa____ phi______ frames - 88.6885 -30.0000 -90.0000 45 #__ type_ start__ end____ width___ exp.time_ 5 omega 20.00 59.00 1.0000 104.0000 omega____ theta____ kappa____ phi______ frames - 88.6885 -30.0000 -30.0000 39 #__ type_ start__ end____ width___ exp.time_ 6 omega 65.00 159.00 1.0000 104.0000 omega____ theta____ kappa____ phi______ frames - 88.6885 45.0000 150.0000 94 #__ type_ start__ end____ width___ exp.time_ 7 omega 57.00 83.00 1.0000 104.0000 omega____ theta____ kappa____ phi______ frames - 88.6885 -94.0000 30.0000 26 #__ type_ start__ end____ width___ exp.time_ 8 omega 69.00 158.00 1.0000 104.0000 omega____ theta____ kappa____ phi______ frames - 88.6885 45.0000 90.0000 89 ; _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0715452000 _diffrn_orient_matrix_UB_12 -0.1038834000 _diffrn_orient_matrix_UB_13 0.0835761000 _diffrn_orient_matrix_UB_21 0.0745923000 _diffrn_orient_matrix_UB_22 0.0185737000 _diffrn_orient_matrix_UB_23 -0.0407777000 _diffrn_orient_matrix_UB_31 0.0364365000 _diffrn_orient_matrix_UB_32 0.1654686000 _diffrn_orient_matrix_UB_33 0.0567675000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_unetI/netI 0.0362 _diffrn_reflns_Laue_measured_fraction_full 0.949 _diffrn_reflns_Laue_measured_fraction_max 0.949 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 4112 _diffrn_reflns_point_group_measured_fraction_full 0.949 _diffrn_reflns_point_group_measured_fraction_max 0.949 _diffrn_reflns_theta_full 62.677 _diffrn_reflns_theta_max 62.677 _diffrn_reflns_theta_min 3.376 _diffrn_source 'Enhance Ultra (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.707 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.95994 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.397 _exptl_crystal_description block _exptl_crystal_F_000 752 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _refine_diff_density_max 0.128 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.038 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 253 _refine_ls_number_reflns 2531 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.107 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0361 _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^)+(0.0427P)^2^+0.0609P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0896 _refine_ls_wR_factor_ref 0.0959 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2129 _reflns_number_total 2531 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; exp_21189.res created by SHELXL-2014/7 TITL exp_21189_a.res in P2(1)/n REM Old TITL exp_21189 in P21/n #14 REM SHELXT solution in P2(1)/n REM R1 0.108, Rweak 0.091, Alpha 0.029, Orientation as input REM Formula found by SHELXT: C25 N O2 CELL 1.54184 15.4892 7.8471 15.5804 90 114.831 90 ZERR 4 0.0008 0.0004 0.0009 0 0.007 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O UNIT 100 60 4 8 L.S. 20 PLAN 4 BOND $H list 4 fmap 2 ACTA REM REM REM WGHT 0.042700 0.060900 FVAR 0.40110 O1 4 0.886266 0.527230 0.549952 11.00000 0.03199 0.04579 = 0.03164 0.00418 0.01760 0.00731 O2 4 0.628583 0.756041 0.488488 11.00000 0.03095 0.04735 = 0.03840 0.00524 0.01399 0.00740 N1 3 0.760581 0.565246 0.835644 11.00000 0.02533 0.03368 = 0.02752 -0.00265 0.01292 -0.00193 C14 1 0.810506 0.645635 0.922937 11.00000 0.03200 0.02747 = 0.02423 0.00286 0.01112 0.00060 C10 1 0.790707 0.552802 0.760999 11.00000 0.02876 0.02861 = 0.02810 -0.00161 0.01409 -0.00212 C11 1 0.877387 0.475481 0.776891 11.00000 0.02943 0.03086 = 0.03003 0.00372 0.01121 0.00228 AFIX 43 H11 2 0.915116 0.430179 0.836043 11.00000 -1.20000 AFIX 0 C6 1 0.755600 0.703360 0.444776 11.00000 0.02831 0.03029 = 0.02810 -0.00470 0.01030 -0.00599 C25 1 0.670790 0.520163 0.828769 11.00000 0.02705 0.02550 = 0.03050 0.00443 0.01220 0.00273 C8 1 0.764029 0.611831 0.599883 11.00000 0.02642 0.02657 = 0.02985 -0.00266 0.01187 -0.00196 C20 1 0.663370 0.567154 0.912286 11.00000 0.02970 0.02925 = 0.03270 0.00556 0.01489 0.00413 C9 1 0.734495 0.618170 0.673047 11.00000 0.02391 0.02843 = 0.03157 -0.00250 0.01331 -0.00072 AFIX 43 H9 2 0.676154 0.667127 0.662264 11.00000 -1.20000 AFIX 0 C13 1 0.850614 0.536022 0.617350 11.00000 0.02810 0.03189 = 0.02992 -0.00209 0.01526 -0.00164 C24 1 0.597550 0.436569 0.755669 11.00000 0.03050 0.03014 = 0.03285 0.00140 0.00973 0.00133 AFIX 43 H24 2 0.602639 0.407881 0.700061 11.00000 -1.20000 AFIX 0 C1 1 0.840924 0.616697 0.467171 11.00000 0.03174 0.03529 = 0.02738 -0.00081 0.01225 -0.00274 C15 1 0.901001 0.716313 0.960051 11.00000 0.03169 0.03568 = 0.03054 0.00509 0.01060 -0.00008 AFIX 43 H15 2 0.939726 0.710267 0.927918 11.00000 -1.20000 AFIX 0 C12 1 0.907125 0.466176 0.705087 11.00000 0.02695 0.03395 = 0.03641 0.00329 0.01404 0.00621 AFIX 43 H12 2 0.964449 0.413658 0.715295 11.00000 -1.20000 AFIX 0 C7 1 0.707696 0.694911 0.508659 11.00000 0.02607 0.02823 = 0.02969 -0.00328 0.01008 -0.00268 C19 1 0.752130 0.649342 0.971848 11.00000 0.03404 0.02817 = 0.02795 0.00390 0.01379 0.00286 C2 1 0.886039 0.618377 0.406641 11.00000 0.03450 0.05247 = 0.03682 0.00082 0.01877 0.00218 AFIX 43 H2 2 0.942094 0.557705 0.421598 11.00000 -1.20000 AFIX 0 C5 1 0.717895 0.798204 0.360998 11.00000 0.03466 0.03372 = 0.03106 0.00028 0.00912 -0.00258 AFIX 43 H5 2 0.661694 0.858804 0.345298 11.00000 -1.20000 AFIX 0 C18 1 0.785289 0.727778 1.060129 11.00000 0.04807 0.03685 = 0.02818 0.00221 0.01851 0.00284 AFIX 43 H18 2 0.748023 0.730073 1.093877 11.00000 -1.20000 AFIX 0 C21 1 0.580487 0.527352 0.923021 11.00000 0.03877 0.04301 = 0.03990 0.00631 0.02334 0.00474 AFIX 43 H21 2 0.574215 0.557950 0.977791 11.00000 -1.20000 AFIX 0 C23 1 0.516751 0.397577 0.768668 11.00000 0.02769 0.03659 = 0.04526 0.00400 0.00791 -0.00154 AFIX 43 H23 2 0.466951 0.340302 0.721194 11.00000 -1.20000 AFIX 0 C22 1 0.508430 0.442391 0.851508 11.00000 0.02992 0.04898 = 0.05395 0.00956 0.02145 0.00117 AFIX 43 H22 2 0.453351 0.414369 0.858417 11.00000 -1.20000 AFIX 0 C17 1 0.873995 0.801769 1.096599 11.00000 0.05270 0.03642 = 0.02731 -0.00193 0.01012 -0.00314 AFIX 43 H17 2 0.896275 0.856173 1.154973 11.00000 -1.20000 AFIX 0 C16 1 0.931059 0.796201 1.047013 11.00000 0.03690 0.03741 = 0.03196 0.00351 0.00490 -0.00548 AFIX 43 H16 2 0.990700 0.847441 1.073096 11.00000 -1.20000 AFIX 0 C4 1 0.763237 0.802674 0.301539 11.00000 0.04853 0.04619 = 0.03137 0.00516 0.01675 -0.00440 AFIX 43 H4 2 0.738103 0.866865 0.246286 11.00000 -1.20000 AFIX 0 C3 1 0.846653 0.710821 0.324565 11.00000 0.04401 0.05929 = 0.03679 0.00198 0.02338 -0.00188 AFIX 43 H3 2 0.876303 0.712054 0.283588 11.00000 -1.20000 AFIX 0 HKLF 4 REM exp_21189_a.res in P2(1)/n REM R1 = 0.0361 for 2129 Fo > 4sig(Fo) and 0.0454 for all 2531 data REM 253 parameters refined using 0 restraints END WGHT 0.0427 0.0609 REM Highest difference peak 0.128, deepest hole -0.188, 1-sigma level 0.038 Q1 1 0.8070 0.6970 0.4680 11.00000 0.05 0.13 Q2 1 0.5543 0.9590 0.3666 11.00000 0.05 0.12 Q3 1 0.8868 0.6944 0.4588 11.00000 0.05 0.12 Q4 1 0.9468 0.3275 0.6942 11.00000 0.05 0.12 REM The information below was added by Olex2. REM REM R1 = 0.0361 for 2129 Fo > 4sig(Fo) and 0.0454 for all 4377 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.13, deepest hole -0.19 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0454 REM R1_gt = 0.0361 REM wR_ref = 0.0959 REM GOOF = 1.107 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 4377 REM Reflections_gt = 2129 REM Parameters = n/a REM Hole = -0.19 REM Peak = 0.13 REM Flack = n/a ; _cod_data_source_file c8sc00429c5.cif _cod_data_source_block CX11 _cod_depositor_comments 'Adding full bibliography for 1549080.cif.' _cod_original_cell_volume 1718.65(18) _cod_database_code 1549080 _shelx_shelxl_version_number 2014/7 _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. ; _reflns_odcompleteness_completeness 96.63 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 58.86 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C11(H11), C9(H9), C24(H24), C15(H15), C12(H12), C2(H2), C5(H5), C18(H18), C21(H21), C23(H23), C22(H22), C17(H17), C16(H16), C4(H4), C3(H3) ; _olex2_submission_special_instructions 'No special instructions were received' 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 O1 O 0.88627(8) 0.52723(17) 0.54995(8) 0.0350(3) Uani 1 1 d . O2 O 0.62858(8) 0.75604(17) 0.48849(8) 0.0391(3) Uani 1 1 d . N1 N 0.76058(9) 0.56525(18) 0.83564(9) 0.0282(3) Uani 1 1 d . C14 C 0.81051(12) 0.6456(2) 0.92294(11) 0.0281(4) Uani 1 1 d . C10 C 0.79071(12) 0.5528(2) 0.76100(11) 0.0278(4) Uani 1 1 d . C11 C 0.87739(12) 0.4755(2) 0.77689(11) 0.0305(4) Uani 1 1 d . H11 H 0.9151 0.4302 0.8360 0.037 Uiso 1 1 calc R C6 C 0.75560(12) 0.7034(2) 0.44478(11) 0.0294(4) Uani 1 1 d . C25 C 0.67079(11) 0.5202(2) 0.82877(11) 0.0276(4) Uani 1 1 d . C8 C 0.76403(11) 0.6118(2) 0.59988(11) 0.0276(4) Uani 1 1 d . C20 C 0.66337(12) 0.5672(2) 0.91229(11) 0.0299(4) Uani 1 1 d . C9 C 0.73450(11) 0.6182(2) 0.67305(11) 0.0274(4) Uani 1 1 d . H9 H 0.6762 0.6671 0.6623 0.033 Uiso 1 1 calc R C13 C 0.85061(12) 0.5360(2) 0.61735(11) 0.0289(4) Uani 1 1 d . C24 C 0.59755(12) 0.4366(2) 0.75567(12) 0.0324(4) Uani 1 1 d . H24 H 0.6026 0.4079 0.7001 0.039 Uiso 1 1 calc R C1 C 0.84092(12) 0.6167(2) 0.46717(11) 0.0315(4) Uani 1 1 d . C15 C 0.90100(12) 0.7163(2) 0.96005(11) 0.0335(4) Uani 1 1 d . H15 H 0.9397 0.7103 0.9279 0.040 Uiso 1 1 calc R C12 C 0.90712(12) 0.4662(2) 0.70509(11) 0.0322(4) Uani 1 1 d . H12 H 0.9644 0.4137 0.7153 0.039 Uiso 1 1 calc R C7 C 0.70770(11) 0.6949(2) 0.50866(11) 0.0285(4) Uani 1 1 d . C19 C 0.75213(12) 0.6493(2) 0.97185(11) 0.0298(4) Uani 1 1 d . C2 C 0.88604(13) 0.6184(3) 0.40664(12) 0.0400(5) Uani 1 1 d . H2 H 0.9421 0.5577 0.4216 0.048 Uiso 1 1 calc R C5 C 0.71790(13) 0.7982(2) 0.36100(11) 0.0347(4) Uani 1 1 d . H5 H 0.6617 0.8588 0.3453 0.042 Uiso 1 1 calc R C18 C 0.78529(14) 0.7278(2) 1.06013(12) 0.0369(4) Uani 1 1 d . H18 H 0.7480 0.7301 1.0939 0.044 Uiso 1 1 calc R C21 C 0.58049(13) 0.5274(3) 0.92302(13) 0.0382(4) Uani 1 1 d . H21 H 0.5742 0.5579 0.9778 0.046 Uiso 1 1 calc R C23 C 0.51675(12) 0.3976(2) 0.76867(13) 0.0390(4) Uani 1 1 d . H23 H 0.4670 0.3403 0.7212 0.047 Uiso 1 1 calc R C22 C 0.50843(13) 0.4424(3) 0.85151(14) 0.0430(5) Uani 1 1 d . H22 H 0.4534 0.4144 0.8584 0.052 Uiso 1 1 calc R C17 C 0.87400(14) 0.8018(2) 1.09660(12) 0.0411(5) Uani 1 1 d . H17 H 0.8963 0.8562 1.1550 0.049 Uiso 1 1 calc R C16 C 0.93106(13) 0.7962(2) 1.04701(12) 0.0387(5) Uani 1 1 d . H16 H 0.9907 0.8474 1.0731 0.046 Uiso 1 1 calc R C4 C 0.76324(14) 0.8027(3) 0.30154(12) 0.0420(5) Uani 1 1 d . H4 H 0.7381 0.8669 0.2463 0.050 Uiso 1 1 calc R C3 C 0.84665(14) 0.7108(3) 0.32457(13) 0.0445(5) Uani 1 1 d . H3 H 0.8763 0.7121 0.2836 0.053 Uiso 1 1 calc R 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 O1 0.0320(6) 0.0458(7) 0.0316(6) 0.0042(5) 0.0176(5) 0.0073(6) O2 0.0309(7) 0.0474(8) 0.0384(7) 0.0052(6) 0.0140(5) 0.0074(6) N1 0.0253(7) 0.0337(8) 0.0275(7) -0.0026(6) 0.0129(6) -0.0019(6) C14 0.0320(9) 0.0275(9) 0.0242(8) 0.0029(7) 0.0111(7) 0.0006(8) C10 0.0288(9) 0.0286(9) 0.0281(8) -0.0016(7) 0.0141(7) -0.0021(8) C11 0.0294(9) 0.0309(9) 0.0300(8) 0.0037(7) 0.0112(7) 0.0023(8) C6 0.0283(9) 0.0303(9) 0.0281(8) -0.0047(7) 0.0103(7) -0.0060(8) C25 0.0270(9) 0.0255(9) 0.0305(8) 0.0044(7) 0.0122(7) 0.0027(7) C8 0.0264(8) 0.0266(9) 0.0298(8) -0.0027(7) 0.0119(7) -0.0020(7) C20 0.0297(9) 0.0293(9) 0.0327(9) 0.0056(7) 0.0149(7) 0.0041(7) C9 0.0239(8) 0.0284(9) 0.0316(9) -0.0025(7) 0.0133(7) -0.0007(7) C13 0.0281(9) 0.0319(9) 0.0299(8) -0.0021(7) 0.0153(7) -0.0016(8) C24 0.0305(9) 0.0301(9) 0.0329(9) 0.0014(7) 0.0097(7) 0.0013(8) C1 0.0317(9) 0.0353(10) 0.0274(8) -0.0008(7) 0.0122(7) -0.0027(8) C15 0.0317(9) 0.0357(10) 0.0305(9) 0.0051(8) 0.0106(7) -0.0001(8) C12 0.0269(9) 0.0340(10) 0.0364(9) 0.0033(8) 0.0140(7) 0.0062(8) C7 0.0261(9) 0.0282(9) 0.0297(8) -0.0033(7) 0.0101(7) -0.0027(8) C19 0.0340(9) 0.0282(9) 0.0279(8) 0.0039(7) 0.0138(7) 0.0029(8) C2 0.0345(10) 0.0525(12) 0.0368(10) 0.0008(9) 0.0188(8) 0.0022(9) C5 0.0347(9) 0.0337(10) 0.0311(9) 0.0003(8) 0.0091(7) -0.0026(8) C18 0.0481(11) 0.0368(10) 0.0282(9) 0.0022(8) 0.0185(8) 0.0028(9) C21 0.0388(10) 0.0430(11) 0.0399(10) 0.0063(9) 0.0233(8) 0.0047(9) C23 0.0277(9) 0.0366(10) 0.0453(10) 0.0040(8) 0.0079(8) -0.0015(8) C22 0.0299(9) 0.0490(12) 0.0539(11) 0.0096(10) 0.0215(9) 0.0012(9) C17 0.0527(12) 0.0364(11) 0.0273(9) -0.0019(8) 0.0101(8) -0.0031(9) C16 0.0369(10) 0.0374(10) 0.0320(9) 0.0035(8) 0.0049(8) -0.0055(9) C4 0.0485(11) 0.0462(12) 0.0314(9) 0.0052(8) 0.0167(8) -0.0044(10) C3 0.0440(11) 0.0593(13) 0.0368(10) 0.0020(9) 0.0234(9) -0.0019(10) 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_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 O1 C13 118.63(13) C14 N1 C10 125.88(14) C25 N1 C14 108.35(13) C25 N1 C10 125.23(13) N1 C14 C19 108.48(14) C15 C14 N1 129.32(15) C15 C14 C19 122.18(15) C11 C10 N1 120.27(14) C9 C10 N1 119.94(15) C9 C10 C11 119.80(15) C10 C11 H11 119.9 C12 C11 C10 120.17(15) C12 C11 H11 119.9 C1 C6 C7 120.20(15) C1 C6 C5 118.25(16) C5 C6 C7 121.55(16) N1 C25 C20 109.24(14) C24 C25 N1 128.86(15) C24 C25 C20 121.86(16) C9 C8 C7 120.54(15) C13 C8 C9 118.48(15) C13 C8 C7 120.82(15) C25 C20 C19 106.62(14) C21 C20 C25 119.30(16) C21 C20 C19 134.07(16) C10 C9 C8 120.80(15) C10 C9 H9 119.6 C8 C9 H9 119.6 O1 C13 C8 122.43(14) O1 C13 C12 116.20(14) C8 C13 C12 121.37(15) C25 C24 H24 121.2 C23 C24 C25 117.52(17) C23 C24 H24 121.2 O1 C1 C6 122.77(15) O1 C1 C2 115.93(16) C2 C1 C6 121.30(16) C14 C15 H15 121.5 C16 C15 C14 117.04(17) C16 C15 H15 121.5 C11 C12 C13 119.36(15) C11 C12 H12 120.3 C13 C12 H12 120.3 O2 C7 C6 122.81(15) O2 C7 C8 122.94(15) C8 C7 C6 114.23(14) C14 C19 C20 107.28(14) C18 C19 C14 119.32(16) C18 C19 C20 133.38(16) C1 C2 H2 120.5 C3 C2 C1 118.98(18) C3 C2 H2 120.5 C6 C5 H5 119.7 C4 C5 C6 120.64(17) C4 C5 H5 119.7 C19 C18 H18 120.5 C17 C18 C19 118.98(17) C17 C18 H18 120.5 C20 C21 H21 120.5 C22 C21 C20 119.05(17) C22 C21 H21 120.5 C24 C23 H23 119.3 C24 C23 C22 121.36(17) C22 C23 H23 119.3 C21 C22 C23 120.90(18) C21 C22 H22 119.6 C23 C22 H22 119.6 C18 C17 H17 119.6 C18 C17 C16 120.82(16) C16 C17 H17 119.6 C15 C16 C17 121.63(17) C15 C16 H16 119.2 C17 C16 H16 119.2 C5 C4 H4 120.2 C5 C4 C3 119.65(17) C3 C4 H4 120.2 C2 C3 C4 121.14(17) C2 C3 H3 119.4 C4 C3 H3 119.4 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C13 1.378(2) O1 C1 1.374(2) O2 C7 1.228(2) N1 C14 1.401(2) N1 C10 1.427(2) N1 C25 1.395(2) C14 C15 1.388(2) C14 C19 1.406(2) C10 C11 1.397(2) C10 C9 1.377(2) C11 H11 0.9300 C11 C12 1.379(2) C6 C1 1.394(2) C6 C7 1.472(2) C6 C5 1.399(2) C25 C20 1.403(2) C25 C24 1.389(2) C8 C9 1.396(2) C8 C13 1.386(2) C8 C7 1.471(2) C20 C19 1.448(2) C20 C21 1.398(3) C9 H9 0.9300 C13 C12 1.389(2) C24 H24 0.9300 C24 C23 1.383(3) C1 C2 1.390(2) C15 H15 0.9300 C15 C16 1.384(3) C12 H12 0.9300 C19 C18 1.393(2) C2 H2 0.9300 C2 C3 1.371(3) C5 H5 0.9300 C5 C4 1.378(3) C18 H18 0.9300 C18 C17 1.376(3) C21 H21 0.9300 C21 C22 1.374(3) C23 H23 0.9300 C23 C22 1.395(3) C22 H22 0.9300 C17 H17 0.9300 C17 C16 1.398(3) C16 H16 0.9300 C4 H4 0.9300 C4 C3 1.389(3) C3 H3 0.9300 loop_ _refln_index_h _refln_index_k _refln_index_l _refln_F_squared_meas _refln_F_squared_sigma 0 0 -1 0.03 0.15 0 0 -2 455.98 6.33 0 0 -3 -0.06 0.33 0 0 -4 112.58 4.64 0 0 -5 -0.39 0.56 0 0 -6 81.77 5.02 0 0 -7 0.77 0.8 0 0 -8 139.67 7.91 0 0 9 0.01 0.4 0 0 -9 -0.28 1.08 0 0 10 41.74 2.41 0 0 -10 41.5 5.05 0 0 11 0.01 0.52 0 0 12 42.07 2.67 0 0 13 0.05 0.56 0 0 14 23.28 2.02 0 0 15 0.46 0.61 0 0 16 7.63 0.99 0 1 -1 12.12 1.04 0 -1 -1 13.88 0.64 0 1 -2 287.81 5.96 0 1 -3 417.86 8.33 0 -1 -4 2.83 0.77 0 1 -4 2.63 0.9 0 1 -5 72.2 4.5 0 -1 -5 80.45 4.38 0 -1 -6 251.99 8.65 0 1 -6 253.08 9.28 0 1 -7 2.45 0.97 0 -1 -7 2.57 1.21 0 -1 -8 89.36 6.23 0 1 -8 88.56 6.56 0 -1 9 3.12 0.76 0 1 9 2.86 0.65 0 -1 9 2.36 0.59 0 -1 -9 3.53 1.42 0 -1 9 2.92 0.73 0 1 -9 2.11 1.15 0 -1 10 2.21 0.73 0 -1 -10 2 1.21 0 -1 10 2.7 0.74 0 1 -10 2.56 1.51 0 1 10 3.18 0.82 0 1 11 3.29 1.05 0 -1 11 3.69 0.86 0 -1 11 2.28 0.83 0 -1 12 10.54 1.37 0 -1 12 10.25 1.24 0 1 12 11.09 1.37 0 1 13 217.3 5.88 0 -1 13 209.39 6.11 0 -1 14 -0.83 0.57 0 1 14 1.25 0.74 0 -1 15 6.62 1.05 0 1 15 5.88 0.98 0 -1 16 26.7 1.78 0 -2 -1 175.32 3.88 0 2 -2 2037.06 19.09 0 -2 -2 1979.24 10.14 0 2 -3 926 14.24 0 2 -4 98.44 5.2 0 2 -5 27.91 3.01 0 -2 -5 29.91 2.76 0 -2 -6 195.95 7.8 0 2 -6 194.76 8.7 0 -2 -7 27.99 3.24 0 2 -7 28.48 3.61 0 -2 -8 5.56 1.6 0 -2 8 5.93 0.82 0 2 -8 4.28 1.67 0 -2 8 6.74 0.89 0 -2 8 7.23 0.96 0 2 -9 19.81 3.58 0 -2 -9 16.81 2.87 0 -2 9 15.62 1.42 0 -2 9 15.68 1.55 0 -2 9 17.5 1.56 0 -2 10 13.88 1.45 0 -2 10 11.8 2.57 0 -2 10 14.56 1.47 0 -2 -10 9.84 2.35 0 -2 11 2.18 0.81 0 -2 11 -0.03 0.46 0 -2 12 11.55 1.45 0 -2 12 13.36 1.69 0 -2 13 25.46 1.99 0 -2 13 25.32 2.17 0 -2 14 3.76 0.91 0 -2 14 4.03 0.85 0 -2 15 1.26 0.59 0 -3 0 -0.07 0.32 0 -3 -1 73.52 3.22 0 -3 1 73.94 4.16 0 3 -4 185.77 7.98 0 3 -5 1.45 0.96 0 -3 -6 4.18 1.31 0 3 -6 3.2 1.26 0 -3 7 -0.1 0.45 0 -3 -7 0.56 0.49 0 3 7 1.27 0.51 0 3 -7 0.12 0.67 0 -3 8 25.21 1.85 0 3 -8 28.74 4.15 0 -3 8 22.99 3.9 0 -3 8 28.11 1.78 0 -3 9 0.34 0.43 0 -3 9 1.33 0.61 0 -3 9 -0.17 0.53 0 -3 10 61.93 3.15 0 -3 10 60.92 2.99 0 -3 11 58.63 3.08 0 -3 11 59.63 3.18 0 -3 12 0.64 0.73 0 -3 12 1.41 0.62 0 -3 13 38.6 2.51 0 -3 13 37.95 2.45 0 -3 14 9.56 1.2 0 -3 14 9.36 1.24 0 -3 15 55.34 2.52 0 -4 0 162.76 6.38 0 -4 1 30.65 3.04 0 -4 2 24.33 2.93 0 -4 3 62.15 5.03 0 -4 4 48.09 4.72 0 -4 5 15.24 1.23 0 -4 5 17.76 3.11 0 4 5 15.7 1.29 0 4 6 16.9 1.43 0 -4 6 19.6 1.53 0 -4 6 17.52 3.21 0 4 7 -0.08 0.38 0 -4 7 0.07 0.49 0 4 8 6.86 1.11 0 -4 8 6.51 1.08 0 -4 9 34.69 2.4 0 -4 10 5.13 1.11 0 -4 11 53.87 3.11 0 -4 12 20.03 1.94 0 -4 13 3.94 0.86 0 -4 14 14.77 1.41 0 5 0 0.03 0.37 0 5 1 0.44 0.45 0 5 -1 0.06 0.3 0 -5 2 0.61 0.46 0 5 2 -0.01 0.33 0 -5 3 30.04 3.87 0 5 3 30.44 1.85 0 -5 4 105.54 3.34 0 5 4 107.6 3.45 0 5 4 99.67 3.46 0 -5 4 101.43 7.42 0 5 5 1.14 0.59 0 -5 5 -0.14 0.51 0 5 5 0.6 0.52 0 5 6 0.17 0.41 0 -5 6 -0.61 0.54 0 5 7 0.01 0.46 0 -5 7 1.01 0.62 0 -5 8 0.04 0.71 0 5 8 0.38 0.6 0 -5 9 0.31 0.55 0 -5 10 25.68 2.13 0 -5 11 2.4 0.79 0 -5 12 8.25 1.23 0 -5 13 1.05 0.53 0 6 0 8.96 1.12 0 6 1 9.31 1.14 0 6 -1 10.24 1.12 0 6 -2 8.19 1.07 0 6 2 7.44 1.04 0 6 3 61.26 2.92 0 6 -3 59.62 2.82 0 6 4 1.52 0.68 0 6 5 11.77 1.48 0 6 6 1.14 0.63 0 -6 6 0.5 0.6 0 6 7 1.27 0.71 0 -6 7 0.16 0.65 0 -6 8 16.1 1.65 0 -6 9 18.12 1.73 0 -6 10 3.03 0.88 0 -6 11 5.11 0.94 0 7 0 -0.44 0.54 0 7 -1 0.49 0.38 0 7 1 0.58 0.48 0 7 2 7.75 1.09 0 7 -2 9.51 1.2 0 7 -3 26.1 1.94 0 7 3 26.34 2.05 0 7 4 48.72 2.73 0 7 -4 46.85 2.58 0 7 5 0.1 0.45 0 7 -5 -0.79 0.48 0 7 -6 1.46 0.57 0 7 6 0.81 0.53 0 7 7 2.2 0.72 0 -7 9 -0.69 0.51 0 8 1 3.18 0.69 0 8 2 11.2 1.22 0 8 3 17.29 1.49 0 8 4 -0.03 0.4 0 8 5 10.71 1.15 -1 0 16 1.08 0.58 -1 0 15 4.49 0.92 -1 0 14 0.48 0.59 -1 0 13 103.24 4.17 -1 0 12 -0.04 0.51 -1 0 11 25.16 1.97 1 0 -10 -0.36 0.52 -1 0 10 0.07 0.42 1 0 -9 5.35 1.69 -1 0 9 5.84 0.9 1 0 -8 0.4 0.79 1 0 -7 12.48 2.21 1 0 -6 -0.22 0.62 1 0 -5 108.66 5.04 1 0 -4 0.45 0.64 1 0 -3 445.78 7.46 1 0 -2 -0.08 0.24 1 0 -1 764.78 5.88 -1 0 -1 1692.19 10.19 1 0 1 1740.12 9.52 -1 0 -2 0.39 0.29 -1 0 -3 1025.29 12.53 -1 0 -4 0.14 0.48 -1 0 -5 5.59 1.37 -1 0 -6 0.4 0.88 1 0 7 128.77 5.75 -1 0 -7 129.68 7.19 -1 0 -8 0.36 0.7 1 0 8 -0.09 0.4 -1 0 -9 0.1 0.92 1 0 9 0.57 0.56 1 0 9 0.31 0.41 1 0 10 -0.09 0.5 -1 0 -10 0.53 0.68 1 0 11 17.16 1.72 1 0 12 -0.19 0.6 1 0 13 83.87 3.83 1 0 14 -0.35 0.47 1 0 15 -0.57 0.43 -1 1 16 3.67 0.7 -1 -1 16 4.46 0.82 -1 1 15 11.15 1.33 -1 -1 15 12.94 1.48 -1 -1 14 93.95 4.06 -1 1 14 98.96 3.91 -1 1 13 5.09 1.02 -1 -1 13 4.97 1.01 -1 -1 12 150.72 4.47 -1 1 12 157.28 4.82 -1 -1 12 154.44 5.06 -1 1 11 11.59 1.25 -1 -1 11 12.86 1.45 -1 -1 11 13.04 1.35 -1 -1 10 1.15 0.53 1 1 -10 2.25 1.29 1 -1 -10 1.13 1.05 -1 -1 10 1.91 0.61 1 -1 -9 253.31 11.21 -1 1 9 249.67 5.48 1 1 -9 246.82 11.49 -1 -1 9 257.56 5.67 -1 -1 9 248.3 4.85 1 1 -8 21.35 3.11 1 -1 -8 17.88 2.8 1 -1 -7 151.42 7.35 1 1 -7 146.94 7.46 1 1 -6 92.38 5.37 1 -1 -6 91.31 5.17 1 1 -5 480.8 10.99 1 -1 -5 483.64 10.62 1 1 -4 86.6 4.16 1 1 -3 628.57 9.51 1 -1 -3 630.22 6.73 1 1 -2 495.12 7 1 -1 -2 496.08 5.56 1 -1 -1 100.7 2.56 1 1 -1 99.69 2.41 1 -1 0 0.28 0.3 1 -1 1 203.56 4.81 -1 1 -1 196.95 4.74 -1 1 -2 21.85 1.83 -1 -1 -2 20.43 1.41 -1 -1 -3 0.27 0.39 1 1 3 0.06 0.11 -1 1 -3 0.48 0.5 1 1 4 0 0.15 -1 -1 -4 0.52 0.61 -1 1 -4 -0.17 0.53 -1 1 -5 248.59 8.66 -1 -1 -5 255.78 7.99 -1 1 -6 92.55 5.84 -1 -1 -6 92.02 5.31 -1 -1 -7 205.95 8.82 -1 1 -7 201.89 9.38 1 -1 8 18.51 1.42 -1 -1 -8 18.34 2.91 1 -1 8 15.95 2.64 1 -1 8 16.18 1.34 -1 1 -8 15.07 2.79 1 -1 9 5.53 1.02 -1 1 -9 5.75 1.83 1 -1 9 6.55 0.94 1 1 9 5.19 0.89 -1 -1 -9 5.71 1.76 -1 -1 -10 40.87 4.89 1 -1 10 39.26 2.43 1 -1 10 38.27 2.29 1 1 10 38.65 2.31 1 1 11 12.18 1.33 1 -1 11 13.52 1.45 1 -1 11 14.7 1.67 1 -1 12 24.25 1.9 1 1 12 24.27 2.01 1 -1 12 13.58 1.63 1 -1 13 0.24 0.6 1 1 13 0.38 0.49 1 1 14 87.64 3.56 1 -1 14 89.51 3.88 1 1 15 2.54 0.63 1 -1 15 3.17 0.72 -1 -2 16 4.99 0.79 -1 -2 15 14.7 1.56 -1 -2 14 78.75 3.25 -1 -2 14 80.89 3.68 -1 -2 13 0.52 0.69 -1 -2 13 -0.34 0.58 -1 -2 12 62.34 3.25 -1 -2 12 60.72 3.06 -1 -2 11 11.07 1.5 -1 -2 11 12.95 1.45 1 2 -10 13.52 3.17 -1 -2 10 12.85 1.44 1 -2 -10 12.43 2.63 -1 -2 10 12.58 1.48 -1 -2 10 12.09 1.31 1 2 -9 -0.26 0.63 -1 -2 9 -0.43 0.47 -1 -2 9 -0.23 0.53 1 -2 -9 0.3 0.63 1 2 -8 74.58 6.15 1 -2 -8 77.91 5.84 1 -2 -7 70.52 5.16 1 2 -7 68.68 5.43 1 -2 -6 43.23 3.67 1 2 -6 42.99 3.92 1 2 -5 105.05 5.62 1 -2 -4 26.04 1.37 1 2 -4 23.64 2.46 1 2 -3 1.06 0.54 1 -2 -3 1.12 0.36 1 -2 -2 114.51 3.3 1 2 -2 117.66 4.22 1 -2 -1 82.35 3.11 1 -2 0 2760.04 19.97 1 -2 1 9999 42.62 -1 -2 -1 9592.41 24.36 -1 2 -2 1955.99 20.36 -1 2 -3 405.32 10.12 -1 -2 -4 17.39 1.87 -1 2 -4 15.84 2.24 -1 2 -5 12.61 2.18 -1 -2 -5 11.54 1.7 -1 2 -6 19.5 2.9 -1 -2 -6 17.47 2.33 1 -2 7 1.36 1.06 -1 2 -7 0.75 0.88 -1 -2 -7 1.16 0.91 -1 2 -8 40.99 4.89 1 -2 8 39.49 2.17 1 -2 8 43.1 2.22 -1 -2 -8 42.18 4.31 1 -2 8 39.48 4.49 -1 2 -9 23.18 3.89 1 -2 9 23.11 1.8 1 -2 9 18.61 3.21 1 -2 9 21.55 1.78 1 -2 10 1.63 0.75 1 -2 10 1.75 0.56 1 -2 11 39.51 2.67 1 -2 11 36.93 2.47 1 -2 12 25.37 2.18 1 -2 12 25.49 2.05 1 -2 13 3.01 0.88 1 -2 13 1.72 0.54 1 -2 14 4.56 0.92 1 -2 14 6.11 0.95 1 -2 15 5.63 0.97 -1 -3 15 65.3 2.83 -1 -3 15 55.55 2.43 -1 -3 14 18.3 1.62 -1 -3 14 21.04 1.79 -1 -3 13 58.53 3.06 -1 -3 13 57.63 3.07 -1 -3 12 61.42 3.19 -1 -3 12 63.03 3.17 -1 -3 11 95.11 3.96 -1 -3 11 89.22 3.71 -1 -3 10 2.3 0.67 -1 -3 10 2.83 0.71 -1 -3 10 2.98 0.88 -1 -3 9 23.49 1.81 -1 -3 9 19.15 1.64 -1 -3 9 22.91 1.71 1 -3 -9 20.54 3.2 1 3 -9 17.44 3.25 -1 -3 8 1.75 0.55 -1 3 8 1.33 0.59 -1 -3 8 1.56 0.51 1 -3 -8 2.81 1.24 1 3 -8 0.7 0.84 -1 -3 8 2.04 0.56 1 -3 -7 140.15 7.53 -1 3 7 148.47 3.91 -1 -3 7 149.6 3.93 1 3 -7 140.6 8.26 1 3 -6 115.89 6.95 1 3 -5 297.43 10.3 1 3 -4 328.73 9.99 1 -3 -2 21.38 1.74 1 -3 -1 46.93 2.87 1 -3 0 12.83 1.7 1 -3 1 137.26 5.93 -1 -3 -1 137.08 3.92 1 -3 2 21.29 2.62 1 -3 3 174.53 7.77 1 -3 4 983.54 19.65 -1 -3 -4 1032.5 15.3 1 -3 5 192.7 9.22 -1 3 -5 188.8 9.04 1 -3 6 18.49 1.39 1 -3 6 18.62 3.13 -1 3 -6 19.04 3.31 1 -3 7 1.06 0.81 1 -3 7 1.59 0.47 -1 3 -7 3.17 1.66 1 -3 7 2.43 0.61 1 -3 8 7.67 1.01 -1 3 -8 8.77 2.31 1 -3 8 5.8 1.98 1 -3 8 8.7 1.17 1 -3 9 16 1.89 1 -3 9 16.46 1.71 1 -3 10 10.72 1.43 1 -3 10 10.78 1.34 1 -3 11 0.24 0.63 1 -3 11 0.49 0.54 1 -3 12 13.5 1.53 1 -3 12 15.01 1.66 1 -3 13 23.88 1.99 1 -3 13 23.77 1.91 1 -3 14 12.07 1.33 1 -3 14 11.37 1.23 -1 -4 14 11.71 1.26 -1 -4 13 2 0.75 -1 -4 12 16.66 1.77 -1 -4 11 -0.29 0.68 -1 -4 10 2.67 0.9 -1 -4 9 93.64 3.84 -1 4 8 8.85 1.26 -1 -4 8 9.34 1.2 -1 -4 7 0.89 0.42 -1 4 7 1.94 0.65 -1 4 6 3.14 0.69 -1 -4 6 3.48 0.77 -1 -4 5 24.41 1.57 -1 4 5 22.48 1.54 1 -4 -1 2.28 0.76 -1 -4 1 3.24 1.06 1 -4 0 112.71 5.62 1 -4 1 33.02 3.29 1 -4 2 304.99 10.72 1 -4 3 247.63 10.35 1 -4 4 817.64 19.89 1 4 5 8.12 0.96 1 -4 5 8.54 2.17 1 -4 5 6.41 0.86 1 4 5 6.92 0.86 1 4 6 14.28 1.36 1 -4 6 14.23 1.38 1 4 6 13.71 1.21 1 -4 6 11.74 2.65 1 4 7 9.07 1.19 1 -4 7 5.67 2.09 1 -4 7 8.55 1.15 1 -4 8 0.41 0.57 1 -4 9 6.33 1.18 1 -4 10 17.33 1.88 1 -4 11 15.27 1.74 1 -4 12 0.49 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