#------------------------------------------------------------------------------ #$Date: 2019-04-19 03:55:33 +0300 (Fri, 19 Apr 2019) $ #$Revision: 214701 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/67/7156785.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_7156785 loop_ _publ_author_name 'Kong, Hongjun' 'Li, Qingrui' 'Yin, Yunnian' 'Huang, Mengmeng' 'Kim, Jung Keun' 'Zhu, Yu' 'Li, Yabo' 'Wu, Yangjie' _publ_section_title ; An efficient light on-off one-pot method for the synthesis of 3-styryl coumarins from aryl alkynoates ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/C9OB00421A _journal_year 2019 _chemical_formula_moiety 'C23 H16 O2' _chemical_formula_sum 'C23 H16 O2' _chemical_formula_weight 324.36 _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' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2018-08-22 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2018-08-23 deposited with the CCDC. 2019-04-16 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 96.908(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.2170(3) _cell_length_b 23.5453(7) _cell_length_c 8.6771(3) _cell_measurement_reflns_used 2545 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 70.5940 _cell_measurement_theta_min 5.1660 _cell_volume 1666.59(10) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _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 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.2312 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -48.00 3.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -33.5000 37.0000 -180.0000 51 #__ type_ start__ end____ width___ exp.time_ 2 omega -59.00 -25.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -33.5000 77.0000 60.0000 34 #__ type_ start__ end____ width___ exp.time_ 3 omega 11.00 36.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -33.5000 77.0000 60.0000 25 #__ type_ start__ end____ width___ exp.time_ 4 omega 84.00 110.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 178.0000 60.0000 26 #__ type_ start__ end____ width___ exp.time_ 5 omega 38.00 77.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 -99.0000 90.0000 39 #__ type_ start__ end____ width___ exp.time_ 6 omega 10.00 39.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 77.0000 -90.0000 29 #__ type_ start__ end____ width___ exp.time_ 7 omega 19.00 63.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 57.0000 -120.0000 44 #__ type_ start__ end____ width___ exp.time_ 8 omega 49.00 103.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 77.0000 -90.0000 54 #__ type_ start__ end____ width___ exp.time_ 9 omega 34.00 90.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 57.0000 -180.0000 56 #__ type_ start__ end____ width___ exp.time_ 10 omega 66.00 91.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 57.0000 -120.0000 25 #__ type_ start__ end____ width___ exp.time_ 11 omega 6.00 35.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 -99.0000 90.0000 29 #__ type_ start__ end____ width___ exp.time_ 12 omega 78.00 108.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -94.0000 30.0000 30 #__ type_ start__ end____ width___ exp.time_ 13 omega 38.00 73.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 -90.0000 35 #__ type_ start__ end____ width___ exp.time_ 14 omega 121.00 178.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 15.0000 -30.0000 57 #__ type_ start__ end____ width___ exp.time_ 15 omega 65.00 90.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 15.0000 -30.0000 25 #__ type_ start__ end____ width___ exp.time_ 16 omega 65.00 95.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -45.0000 -180.0000 30 #__ type_ start__ end____ width___ exp.time_ 17 omega 37.00 85.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 0.0000 48 #__ type_ start__ end____ width___ exp.time_ 18 omega 42.00 91.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 -60.0000 49 #__ type_ start__ end____ width___ exp.time_ 19 omega 37.00 112.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -111.0000 -30.0000 75 #__ type_ start__ end____ width___ exp.time_ 20 omega 104.00 165.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 45.0000 30.0000 61 #__ type_ start__ end____ width___ exp.time_ 21 omega 45.00 137.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -77.0000 90.0000 92 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0001817000 _diffrn_orient_matrix_UB_12 0.0651995000 _diffrn_orient_matrix_UB_13 -0.0150685000 _diffrn_orient_matrix_UB_21 0.1886872000 _diffrn_orient_matrix_UB_22 0.0001473000 _diffrn_orient_matrix_UB_23 0.0285104000 _diffrn_orient_matrix_UB_31 0.0073563000 _diffrn_orient_matrix_UB_32 -0.0055771000 _diffrn_orient_matrix_UB_33 -0.1759255000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0206 _diffrn_reflns_av_unetI/netI 0.0279 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 6277 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 67.064 _diffrn_reflns_theta_max 67.064 _diffrn_reflns_theta_min 3.755 _diffrn_source 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.645 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.82620 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) 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 1.293 _exptl_crystal_description prism _exptl_crystal_F_000 680 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.239 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.038 _refine_ls_extinction_coef 0.0033(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 227 _refine_ls_number_reflns 2957 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.047 _refine_ls_R_factor_all 0.0554 _refine_ls_R_factor_gt 0.0470 _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^)+(0.0846P)^2^+0.1340P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1356 _refine_ls_wR_factor_ref 0.1463 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2455 _reflns_number_total 2957 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; 201808344.res created by SHELXL-2014/7 TITL 201808344 in P21/c #14 REM reset to P21/c #14 CELL 1.54184 8.216984 23.545289 8.677123 90 96.9081 90 ZERR 4 0.000289 0.000746 0.000294 0 0.0035 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H O UNIT 92 64 8 L.S. 4 0 0 PLAN 20 SIZE 0.13 0.14 0.18 MPLA C1 C2 C11 C18 C19 C20 C21 C22 C23 O1 MPLA C5 C6 C7 C8 C9 C10 MPLA C12 C13 C14 C15 C16 C17 BOND $h conf fmap 2 acta REM REM REM WGHT 0.084600 0.134000 EXTI 0.003282 FVAR 6.88455 C1 1 0.356901 0.551243 0.742023 11.00000 0.05855 0.05541 = 0.04562 -0.00049 0.00891 0.01007 C2 1 0.236293 0.591920 0.789598 11.00000 0.04627 0.04253 = 0.04196 0.00113 0.00896 0.00215 C3 1 0.264513 0.617776 0.943500 11.00000 0.04504 0.04690 = 0.04291 -0.00034 0.00628 0.00582 AFIX 43 H3 2 0.193879 0.647415 0.960144 11.00000 -1.20000 AFIX 0 C4 1 0.375025 0.605634 1.063246 11.00000 0.04943 0.05066 = 0.04458 0.00141 0.00542 0.00830 AFIX 43 H4 2 0.446949 0.575888 1.051437 11.00000 -1.20000 AFIX 0 C5 1 0.392790 0.635360 1.212638 11.00000 0.04302 0.05011 = 0.04288 0.00373 0.00482 -0.00247 C6 1 0.503418 0.615241 1.334794 11.00000 0.04924 0.06167 = 0.05360 0.00057 -0.00441 0.00521 AFIX 43 H6 2 0.566571 0.583399 1.319692 11.00000 -1.20000 AFIX 0 C7 1 0.520990 0.641724 1.477880 11.00000 0.05231 0.08076 = 0.04791 0.00391 -0.00727 -0.00550 AFIX 43 H7 2 0.595410 0.627463 1.557735 11.00000 -1.20000 AFIX 0 C8 1 0.430266 0.688593 1.503232 11.00000 0.05951 0.07844 = 0.04394 -0.00968 0.00647 -0.01178 AFIX 43 H8 2 0.442794 0.706370 1.599641 11.00000 -1.20000 AFIX 0 C9 1 0.319859 0.709297 1.384390 11.00000 0.07341 0.06894 = 0.05368 -0.00932 0.00753 0.01111 AFIX 43 H9 2 0.257546 0.741211 1.400876 11.00000 -1.20000 AFIX 0 C10 1 0.301025 0.683128 1.241425 11.00000 0.06375 0.06176 = 0.04429 0.00043 0.00114 0.01343 AFIX 43 H10 2 0.225676 0.697603 1.162652 11.00000 -1.20000 AFIX 0 C11 1 0.103323 0.606654 0.686691 11.00000 0.04487 0.04239 = 0.03963 -0.00069 0.00775 -0.00261 C12 1 -0.021417 0.647393 0.731804 11.00000 0.04242 0.05306 = 0.03569 -0.00592 -0.00031 0.00212 C13 1 -0.136059 0.630591 0.827622 11.00000 0.05869 0.06696 = 0.05025 -0.00568 0.01423 0.00033 AFIX 43 H13 2 -0.137066 0.593314 0.862934 11.00000 -1.20000 AFIX 0 C14 1 -0.249304 0.669450 0.870785 11.00000 0.05763 0.10851 = 0.06309 -0.02132 0.01699 0.00535 AFIX 43 H14 2 -0.327142 0.657932 0.933723 11.00000 -1.20000 AFIX 0 C15 1 -0.247112 0.724722 0.821193 11.00000 0.06556 0.09391 = 0.06907 -0.02914 -0.00604 0.03211 AFIX 43 H15 2 -0.321679 0.750797 0.852285 11.00000 -1.20000 AFIX 0 C16 1 -0.134686 0.741425 0.725652 11.00000 0.08957 0.06196 = 0.07048 -0.00654 -0.00463 0.02515 AFIX 43 H16 2 -0.133068 0.778874 0.691795 11.00000 -1.20000 AFIX 0 C17 1 -0.024058 0.702799 0.679707 11.00000 0.06638 0.05598 = 0.05798 -0.00064 0.00831 0.00570 AFIX 43 H17 2 0.049851 0.714236 0.612651 11.00000 -1.20000 AFIX 0 C18 1 0.082690 0.583247 0.531324 11.00000 0.04923 0.04521 = 0.04069 -0.00179 0.00980 -0.00679 C19 1 0.197897 0.544579 0.491001 11.00000 0.05477 0.04712 = 0.04512 -0.00344 0.01270 -0.00650 C20 1 0.188969 0.520539 0.344704 11.00000 0.07009 0.05883 = 0.05479 -0.01484 0.02020 -0.00747 AFIX 43 H20 2 0.268146 0.494858 0.320695 11.00000 -1.20000 AFIX 0 C21 1 0.061151 0.535332 0.235966 11.00000 0.07911 0.07147 = 0.04251 -0.01296 0.01190 -0.01857 AFIX 43 H21 2 0.053593 0.519497 0.137174 11.00000 -1.20000 AFIX 0 C22 1 -0.056436 0.573398 0.271111 11.00000 0.06887 0.07607 = 0.04290 -0.00495 -0.00002 -0.01251 AFIX 43 H22 2 -0.142724 0.582950 0.196205 11.00000 -1.20000 AFIX 0 C23 1 -0.046523 0.597391 0.417171 11.00000 0.05496 0.06449 = 0.04456 -0.00432 0.00366 -0.00372 AFIX 43 H23 2 -0.126116 0.623114 0.439987 11.00000 -1.20000 AFIX 0 O1 3 0.327916 0.528554 0.595758 11.00000 0.06299 0.05465 = 0.05121 -0.00808 0.01294 0.01118 O2 3 0.480319 0.535904 0.819277 11.00000 0.07946 0.10328 = 0.05899 -0.00800 0.00020 0.04867 HKLF 4 REM 201808344 in P21/c #14 REM R1 = 0.0470 for 2455 Fo > 4sig(Fo) and 0.0554 for all 2957 data REM 227 parameters refined using 0 restraints END WGHT 0.0845 0.1336 REM Highest difference peak 0.239, deepest hole -0.172, 1-sigma level 0.038 Q1 1 0.3832 0.5173 0.8441 11.00000 0.05 0.24 Q2 1 0.3829 0.6742 1.2073 11.00000 0.05 0.17 Q3 1 0.3600 0.6319 0.9808 11.00000 0.05 0.17 Q4 1 0.0107 0.6763 0.7737 11.00000 0.05 0.15 Q5 1 0.5061 0.5628 1.3347 11.00000 0.05 0.15 Q6 1 0.1499 0.5794 0.7707 11.00000 0.05 0.14 Q7 1 0.4971 0.6390 1.2359 11.00000 0.05 0.14 Q8 1 0.3834 0.4883 0.5911 11.00000 0.05 0.14 Q9 1 -0.2036 0.7225 0.7513 11.00000 0.05 0.13 Q10 1 0.1050 0.5532 0.5247 11.00000 0.05 0.13 Q11 1 0.2998 0.6461 1.2388 11.00000 0.05 0.13 Q12 1 -0.0540 0.6696 0.6598 11.00000 0.05 0.13 Q13 1 0.1461 0.6861 1.1655 11.00000 0.05 0.12 Q14 1 0.4309 0.7133 1.4464 11.00000 0.05 0.12 Q15 1 0.2244 0.6698 0.9396 11.00000 0.05 0.12 Q16 1 0.2183 0.6080 0.7511 11.00000 0.05 0.12 Q17 1 0.1691 0.5198 0.4405 11.00000 0.05 0.12 Q18 1 0.3229 0.7571 1.3839 11.00000 0.05 0.12 Q19 1 0.1055 0.5178 0.3462 11.00000 0.05 0.11 Q20 1 0.0529 0.6280 0.7154 11.00000 0.05 0.11 REM The information below was added by Olex2. REM REM R1 = 0.0470 for 2455 Fo > 4sig(Fo) and 0.0554 for all 6406 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.24, deepest hole -0.17 REM Mean Shift 0, Max Shift 0.001. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0554 REM R1_gt = 0.0470 REM wR_ref = 0.1463 REM GOOF = 1.047 REM Shift_max = 0.001 REM Shift_mean = 0 REM Reflections_all = 6406 REM Reflections_gt = 2455 REM Parameters = n/a REM Hole = -0.17 REM Peak = 0.24 REM Flack = n/a ; _cod_data_source_file c9ob00421a2.cif _cod_data_source_block 201808344 _cod_database_code 7156785 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_formula C15H15O3N2 _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 0.921 _shelx_estimated_absorpt_t_min 0.893 _reflns_odcompleteness_completeness 99.48 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23) ; _olex2_submission_special_instructions 'No special instructions were received' 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 C1 C 0.3569(2) 0.55124(7) 0.7420(2) 0.0530(4) Uani 1 1 d . C2 C 0.23629(19) 0.59192(6) 0.78960(18) 0.0433(4) Uani 1 1 d . C3 C 0.26451(18) 0.61778(7) 0.94350(18) 0.0449(4) Uani 1 1 d . H3 H 0.1939 0.6474 0.9601 0.054 Uiso 1 1 calc R C4 C 0.3750(2) 0.60563(7) 1.06325(19) 0.0482(4) Uani 1 1 d . H4 H 0.4469 0.5759 1.0514 0.058 Uiso 1 1 calc R C5 C 0.39279(18) 0.63536(7) 1.21264(18) 0.0454(4) Uani 1 1 d . C6 C 0.5034(2) 0.61524(8) 1.3348(2) 0.0557(4) Uani 1 1 d . H6 H 0.5666 0.5834 1.3197 0.067 Uiso 1 1 calc R C7 C 0.5210(2) 0.64172(9) 1.4779(2) 0.0614(5) Uani 1 1 d . H7 H 0.5954 0.6275 1.5577 0.074 Uiso 1 1 calc R C8 C 0.4303(2) 0.68859(9) 1.5032(2) 0.0606(5) Uani 1 1 d . H8 H 0.4428 0.7064 1.5996 0.073 Uiso 1 1 calc R C9 C 0.3199(3) 0.70930(9) 1.3844(2) 0.0654(5) Uani 1 1 d . H9 H 0.2575 0.7412 1.4009 0.078 Uiso 1 1 calc R C10 C 0.3010(2) 0.68313(8) 1.2414(2) 0.0570(4) Uani 1 1 d . H10 H 0.2257 0.6976 1.1627 0.068 Uiso 1 1 calc R C11 C 0.10332(18) 0.60665(6) 0.68669(17) 0.0421(4) Uani 1 1 d . C12 C -0.02142(18) 0.64739(7) 0.73180(17) 0.0441(4) Uani 1 1 d . C13 C -0.1361(2) 0.63059(8) 0.8276(2) 0.0580(4) Uani 1 1 d . H13 H -0.1371 0.5933 0.8629 0.070 Uiso 1 1 calc R C14 C -0.2493(2) 0.66945(12) 0.8708(3) 0.0756(6) Uani 1 1 d . H14 H -0.3271 0.6579 0.9337 0.091 Uiso 1 1 calc R C15 C -0.2471(3) 0.72472(11) 0.8212(3) 0.0773(7) Uani 1 1 d . H15 H -0.3217 0.7508 0.8523 0.093 Uiso 1 1 calc R C16 C -0.1347(3) 0.74143(9) 0.7257(3) 0.0752(6) Uani 1 1 d . H16 H -0.1331 0.7789 0.6918 0.090 Uiso 1 1 calc R C17 C -0.0241(2) 0.70280(8) 0.6797(2) 0.0600(5) Uani 1 1 d . H17 H 0.0499 0.7142 0.6127 0.072 Uiso 1 1 calc R C18 C 0.0827(2) 0.58325(6) 0.53132(18) 0.0447(4) Uani 1 1 d . C19 C 0.1979(2) 0.54458(7) 0.49100(19) 0.0485(4) Uani 1 1 d . C20 C 0.1890(2) 0.52054(8) 0.3447(2) 0.0602(5) Uani 1 1 d . H20 H 0.2681 0.4949 0.3207 0.072 Uiso 1 1 calc R C21 C 0.0612(3) 0.53533(9) 0.2360(2) 0.0640(5) Uani 1 1 d . H21 H 0.0536 0.5195 0.1372 0.077 Uiso 1 1 calc R C22 C -0.0564(3) 0.57340(9) 0.2711(2) 0.0632(5) Uani 1 1 d . H22 H -0.1427 0.5830 0.1962 0.076 Uiso 1 1 calc R C23 C -0.0465(2) 0.59739(8) 0.4172(2) 0.0549(4) Uani 1 1 d . H23 H -0.1261 0.6231 0.4400 0.066 Uiso 1 1 calc R O1 O 0.32792(15) 0.52855(5) 0.59576(14) 0.0558(3) Uani 1 1 d . O2 O 0.48032(19) 0.53590(7) 0.81928(17) 0.0812(5) Uani 1 1 d . 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 C1 0.0586(10) 0.0554(9) 0.0456(8) -0.0005(7) 0.0089(7) 0.0101(7) C2 0.0463(8) 0.0425(7) 0.0420(8) 0.0011(6) 0.0090(6) 0.0022(6) C3 0.0450(8) 0.0469(7) 0.0429(8) -0.0003(6) 0.0063(6) 0.0058(6) C4 0.0494(8) 0.0507(8) 0.0446(8) 0.0014(7) 0.0054(7) 0.0083(6) C5 0.0430(8) 0.0501(8) 0.0429(8) 0.0037(6) 0.0048(6) -0.0025(6) C6 0.0492(9) 0.0617(10) 0.0536(9) 0.0006(8) -0.0044(7) 0.0052(7) C7 0.0523(9) 0.0808(12) 0.0479(9) 0.0039(8) -0.0073(7) -0.0055(8) C8 0.0595(10) 0.0784(12) 0.0439(9) -0.0097(8) 0.0065(7) -0.0118(9) C9 0.0734(12) 0.0689(11) 0.0537(10) -0.0093(8) 0.0075(9) 0.0111(9) C10 0.0638(10) 0.0618(10) 0.0443(8) 0.0004(7) 0.0011(7) 0.0134(8) C11 0.0449(8) 0.0424(7) 0.0396(8) -0.0007(6) 0.0078(6) -0.0026(6) C12 0.0424(7) 0.0531(8) 0.0357(7) -0.0059(6) -0.0003(6) 0.0021(6) C13 0.0587(10) 0.0670(11) 0.0502(9) -0.0057(8) 0.0142(8) 0.0003(8) C14 0.0576(11) 0.1085(18) 0.0631(12) -0.0213(11) 0.0170(9) 0.0053(11) C15 0.0656(12) 0.0939(16) 0.0691(13) -0.0291(11) -0.0060(10) 0.0321(11) C16 0.0896(15) 0.0620(11) 0.0705(12) -0.0065(9) -0.0046(11) 0.0252(10) C17 0.0664(11) 0.0560(10) 0.0580(10) -0.0006(8) 0.0083(8) 0.0057(8) C18 0.0492(8) 0.0452(8) 0.0407(8) -0.0018(6) 0.0098(6) -0.0068(6) C19 0.0548(9) 0.0471(8) 0.0451(8) -0.0034(6) 0.0127(7) -0.0065(6) C20 0.0701(11) 0.0588(10) 0.0548(10) -0.0148(8) 0.0202(8) -0.0075(8) C21 0.0791(12) 0.0715(11) 0.0425(9) -0.0130(8) 0.0119(8) -0.0186(9) C22 0.0689(11) 0.0761(12) 0.0429(9) -0.0050(8) 0.0000(8) -0.0125(9) C23 0.0550(9) 0.0645(10) 0.0446(9) -0.0043(7) 0.0037(7) -0.0037(7) O1 0.0630(7) 0.0547(6) 0.0512(7) -0.0081(5) 0.0129(5) 0.0112(5) O2 0.0795(9) 0.1033(11) 0.0590(8) -0.0080(7) 0.0002(7) 0.0487(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' 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 O1 C1 C2 117.71(14) O2 C1 C2 126.17(16) O2 C1 O1 116.11(15) C3 C2 C1 119.29(14) C11 C2 C1 119.53(14) C11 C2 C3 121.12(14) C2 C3 H3 114.9 C4 C3 C2 130.16(15) C4 C3 H3 114.9 C3 C4 H4 117.4 C3 C4 C5 125.19(15) C5 C4 H4 117.4 C6 C5 C4 119.81(15) C10 C5 C4 123.08(14) C10 C5 C6 117.10(15) C5 C6 H6 119.4 C7 C6 C5 121.22(17) C7 C6 H6 119.4 C6 C7 H7 119.7 C8 C7 C6 120.66(16) C8 C7 H7 119.7 C7 C8 H8 120.4 C7 C8 C9 119.26(16) C9 C8 H8 120.4 C8 C9 H9 119.7 C10 C9 C8 120.55(18) C10 C9 H9 119.7 C5 C10 H10 119.4 C9 C10 C5 121.20(16) C9 C10 H10 119.4 C2 C11 C12 120.77(13) C2 C11 C18 120.37(14) C18 C11 C12 118.85(13) C13 C12 C11 120.81(15) C17 C12 C11 120.44(15) C17 C12 C13 118.75(16) C12 C13 H13 120.0 C12 C13 C14 119.96(19) C14 C13 H13 120.0 C13 C14 H14 119.8 C15 C14 C13 120.4(2) C15 C14 H14 119.8 C14 C15 H15 120.1 C16 C15 C14 119.81(18) C16 C15 H15 120.1 C15 C16 H16 120.0 C15 C16 C17 120.1(2) C17 C16 H16 120.0 C12 C17 H17 119.5 C16 C17 C12 120.93(19) C16 C17 H17 119.5 C19 C18 C11 118.52(15) C19 C18 C23 117.33(15) C23 C18 C11 124.15(15) C20 C19 C18 122.48(17) O1 C19 C18 120.96(14) O1 C19 C20 116.56(16) C19 C20 H20 120.7 C21 C20 C19 118.66(18) C21 C20 H20 120.7 C20 C21 H21 119.6 C20 C21 C22 120.84(16) C22 C21 H21 119.6 C21 C22 H22 119.9 C21 C22 C23 120.22(18) C23 C22 H22 119.9 C18 C23 H23 119.8 C22 C23 C18 120.48(18) C22 C23 H23 119.8 C19 O1 C1 122.80(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.473(2) C1 O1 1.371(2) C1 O2 1.202(2) C2 C3 1.461(2) C2 C11 1.370(2) C3 H3 0.9300 C3 C4 1.326(2) C4 H4 0.9300 C4 C5 1.465(2) C5 C6 1.394(2) C5 C10 1.393(2) C6 H6 0.9300 C6 C7 1.381(3) C7 H7 0.9300 C7 C8 1.364(3) C8 H8 0.9300 C8 C9 1.378(3) C9 H9 0.9300 C9 C10 1.377(3) C10 H10 0.9300 C11 C12 1.490(2) C11 C18 1.447(2) C12 C13 1.387(2) C12 C17 1.380(2) C13 H13 0.9300 C13 C14 1.388(3) C14 H14 0.9300 C14 C15 1.371(4) C15 H15 0.9300 C15 C16 1.371(3) C16 H16 0.9300 C16 C17 1.378(3) C17 H17 0.9300 C18 C19 1.388(2) C18 C23 1.402(2) C19 C20 1.384(2) C19 O1 1.370(2) C20 H20 0.9300 C20 C21 1.370(3) C21 H21 0.9300 C21 C22 1.379(3) C22 H22 0.9300 C22 C23 1.381(3) C23 H23 0.9300 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 C1 C2 C3 C4 -9.9(3) C1 C2 C11 C12 179.57(14) C1 C2 C11 C18 -1.1(2) C2 C1 O1 C19 3.8(2) C2 C3 C4 C5 179.18(15) C2 C11 C12 C13 -76.0(2) C2 C11 C12 C17 103.55(18) C2 C11 C18 C19 1.7(2) C2 C11 C18 C23 -177.83(15) C3 C2 C11 C12 -3.2(2) C3 C2 C11 C18 176.16(13) C3 C4 C5 C6 173.90(16) C3 C4 C5 C10 -4.8(3) C4 C5 C6 C7 -178.87(15) C4 C5 C10 C9 179.01(17) C5 C6 C7 C8 -0.2(3) C6 C5 C10 C9 0.3(3) C6 C7 C8 C9 0.2(3) C7 C8 C9 C10 -0.1(3) C8 C9 C10 C5 -0.2(3) C10 C5 C6 C7 -0.1(3) C11 C2 C3 C4 172.83(16) C11 C12 C13 C14 178.76(16) C11 C12 C17 C16 -177.41(17) C11 C18 C19 C20 -179.27(15) C11 C18 C19 O1 0.4(2) C11 C18 C23 C22 179.48(15) C12 C11 C18 C19 -178.91(13) C12 C11 C18 C23 1.5(2) C12 C13 C14 C15 -1.0(3) C13 C12 C17 C16 2.1(3) C13 C14 C15 C16 1.4(3) C14 C15 C16 C17 -0.1(3) C15 C16 C17 C12 -1.7(3) C17 C12 C13 C14 -0.8(3) C18 C11 C12 C13 104.68(17) C18 C11 C12 C17 -75.81(19) C18 C19 C20 C21 -0.3(3) C18 C19 O1 C1 -3.2(2) C19 C18 C23 C22 -0.1(2) C19 C20 C21 C22 0.0(3) C20 C19 O1 C1 176.42(15) C20 C21 C22 C23 0.2(3) C21 C22 C23 C18 -0.2(3) C23 C18 C19 C20 0.3(2) C23 C18 C19 O1 179.95(14) O1 C1 C2 C3 -178.88(14) O1 C1 C2 C11 -1.6(2) O1 C19 C20 C21 -179.93(15) O2 C1 C2 C3 0.7(3) O2 C1 C2 C11 178.03(19) O2 C1 O1 C19 -175.87(17)