#------------------------------------------------------------------------------ #$Date: 2019-04-19 03:55:33 +0300 (Fri, 19 Apr 2019) $ #$Revision: 214701 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/67/7156786.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_7156786 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 'C24 H18 O2' _chemical_formula_sum 'C24 H18 O2' _chemical_formula_weight 338.38 _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 2018-04-10 _audit_creation_method ; Olex2 1.2 (compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486) ; _audit_update_record ; 2018-08-23 deposited with the CCDC. 2019-04-16 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 94.497(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.1912(4) _cell_length_b 25.2962(16) _cell_length_c 8.6202(3) _cell_measurement_reflns_used 1668 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 68.7290 _cell_measurement_theta_min 5.4060 _cell_volume 1780.66(16) _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 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -102.00 -15.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -33.5000 -57.0000 0.0000 87 #__ type_ start__ end____ width___ exp.time_ 2 omega -108.00 -47.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -33.5000 178.0000 -90.0000 61 #__ type_ start__ end____ width___ exp.time_ 3 omega 64.00 104.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 57.0000 60.0000 40 #__ type_ start__ end____ width___ exp.time_ 4 omega 11.00 70.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 77.0000 120.0000 59 #__ type_ start__ end____ width___ exp.time_ 5 omega 57.00 108.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 178.0000 -120.0000 51 #__ type_ start__ end____ width___ exp.time_ 6 omega 19.00 49.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 57.0000 60.0000 30 #__ type_ start__ end____ width___ exp.time_ 7 omega 41.00 67.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 -19.0000 120.0000 26 #__ type_ start__ end____ width___ exp.time_ 8 omega 79.00 105.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 178.0000 -90.0000 26 #__ type_ start__ end____ width___ exp.time_ 9 omega -31.00 42.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 -57.0000 -90.0000 73 #__ type_ start__ end____ width___ exp.time_ 10 omega -21.00 5.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 -19.0000 120.0000 26 #__ type_ start__ end____ width___ exp.time_ 11 omega 119.00 145.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -15.0000 -60.0000 26 #__ type_ start__ end____ width___ exp.time_ 12 omega 43.00 77.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 -180.0000 34 #__ type_ start__ end____ width___ exp.time_ 13 omega 39.00 99.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -15.0000 -60.0000 60 #__ type_ start__ end____ width___ exp.time_ 14 omega 45.00 71.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -45.0000 -120.0000 26 #__ type_ start__ end____ width___ exp.time_ 15 omega 41.00 96.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -45.0000 60.0000 55 #__ type_ start__ end____ width___ exp.time_ 16 omega 131.00 172.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 111.0000 -150.0000 41 #__ type_ start__ end____ width___ exp.time_ 17 omega 45.00 84.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 -120.0000 39 #__ type_ start__ end____ width___ exp.time_ 18 omega 54.00 83.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 -90.0000 29 #__ type_ start__ end____ width___ exp.time_ 19 omega 61.00 107.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -94.0000 120.0000 46 #__ type_ start__ end____ width___ exp.time_ 20 omega 49.00 127.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -61.0000 -30.0000 78 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.1164744000 _diffrn_orient_matrix_UB_12 -0.0052329000 _diffrn_orient_matrix_UB_13 0.1312340000 _diffrn_orient_matrix_UB_21 0.1413104000 _diffrn_orient_matrix_UB_22 0.0148994000 _diffrn_orient_matrix_UB_23 0.1205318000 _diffrn_orient_matrix_UB_31 -0.0459103000 _diffrn_orient_matrix_UB_32 0.0588497000 _diffrn_orient_matrix_UB_33 -0.0189365000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_unetI/netI 0.0347 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 6554 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 67.048 _diffrn_reflns_theta_max 67.048 _diffrn_reflns_theta_min 5.417 _diffrn_source 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.624 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.94309 _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 yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.262 _exptl_crystal_description prism _exptl_crystal_F_000 712 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.167 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.031 _refine_ls_extinction_coef 0.0025(4) _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 1.026 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 237 _refine_ls_number_reflns 3173 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.026 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_gt 0.0492 _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^)+(0.0684P)^2^+0.1700P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1321 _refine_ls_wR_factor_ref 0.1558 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2172 _reflns_number_total 3173 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; 201803207.res created by SHELXL-2014/7 TITL 201803207 in P21/c #14 REM reset to P21/c #14 CELL 1.54184 8.19124 25.296227 8.620199 90 94.497 90 ZERR 4 0.000398 0.001556 0.000293 0 0.0036 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H O UNIT 96 72 8 L.S. 4 0 0 PLAN 20 SIZE 0.13 0.14 0.18 MPLA C1 C2 C3 C4 C5 C6 C7 C8 C9 O2 MPLA C11 C12 C13 C14 C15 C16 C17 C18 MPLA C19 C20 C21 C22 C23 C24 bond $h conf fmap 2 acta REM REM REM WGHT 0.068400 0.170000 EXTI 0.002468 FVAR 6.48535 C1 1 0.070954 0.561613 0.166685 11.00000 0.07315 0.06904 = 0.06558 -0.00573 0.01085 -0.01825 C2 1 0.187406 0.600564 0.113864 11.00000 0.05932 0.05255 = 0.06033 -0.00544 0.01262 -0.00428 C3 1 0.318426 0.615596 0.212091 11.00000 0.05517 0.04956 = 0.05709 -0.00100 0.01200 -0.00037 C4 1 0.344809 0.592465 0.365655 11.00000 0.06124 0.05060 = 0.05800 0.00293 0.01303 0.00080 C5 1 0.240515 0.552368 0.407306 11.00000 0.07054 0.05209 = 0.06167 -0.00205 0.01419 -0.00226 C6 1 0.260506 0.527105 0.549445 11.00000 0.08629 0.05363 = 0.06884 0.00693 0.02359 -0.00259 AFIX 43 H6 2 0.188898 0.500293 0.573210 11.00000 -1.20000 AFIX 0 C7 1 0.386434 0.541611 0.655967 11.00000 0.08170 0.05870 = 0.06405 0.00892 0.01794 0.01194 C8 1 0.490409 0.582197 0.617448 11.00000 0.07473 0.07709 = 0.06476 0.01094 0.00190 0.00015 AFIX 43 H8 2 0.574843 0.592686 0.689271 11.00000 -1.20000 AFIX 0 C9 1 0.471092 0.607177 0.475384 11.00000 0.06566 0.06753 = 0.06580 0.01035 0.00641 -0.00590 AFIX 43 H9 2 0.542709 0.634068 0.452274 11.00000 -1.20000 AFIX 0 C10 1 0.411838 0.514242 0.810717 11.00000 0.10747 0.07817 = 0.07221 0.02053 0.01875 0.01555 AFIX 137 H10A 2 0.362501 0.534722 0.888318 11.00000 -1.50000 H10B 2 0.527023 0.510664 0.838944 11.00000 -1.50000 H10C 2 0.362218 0.479856 0.803741 11.00000 -1.50000 AFIX 0 C11 1 0.156451 0.624440 -0.039795 11.00000 0.05801 0.06013 = 0.05920 -0.00608 0.00620 -0.00489 AFIX 43 H11 2 0.222437 0.653238 -0.059165 11.00000 -1.20000 AFIX 0 C12 1 0.048534 0.611248 -0.155721 11.00000 0.06675 0.06459 = 0.06782 -0.01005 0.00756 -0.01050 AFIX 43 H12 2 -0.019419 0.582594 -0.140162 11.00000 -1.20000 AFIX 0 C13 1 0.027419 0.638163 -0.306777 11.00000 0.05446 0.07205 = 0.05944 -0.01236 0.00463 0.00144 C14 1 0.105910 0.684994 -0.338838 11.00000 0.08329 0.08461 = 0.06061 -0.00337 -0.00380 -0.01582 AFIX 43 H14 2 0.175656 0.700560 -0.261618 11.00000 -1.20000 AFIX 0 C15 1 0.083208 0.708991 -0.481930 11.00000 0.09621 0.10562 = 0.06816 0.00853 0.00337 -0.00758 AFIX 43 H15 2 0.136986 0.740513 -0.499995 11.00000 -1.20000 AFIX 0 C16 1 -0.018361 0.686742 -0.598467 11.00000 0.07272 0.11961 = 0.05973 -0.00193 0.00495 0.01971 AFIX 43 H16 2 -0.032985 0.702796 -0.695620 11.00000 -1.20000 AFIX 0 C17 1 -0.097439 0.640756 -0.569556 11.00000 0.06476 0.12111 = 0.06601 -0.02235 -0.00996 0.01102 AFIX 43 H17 2 -0.166584 0.625446 -0.647718 11.00000 -1.20000 AFIX 0 C18 1 -0.076147 0.616690 -0.425923 11.00000 0.06674 0.09046 = 0.07580 -0.01724 -0.00356 -0.00622 AFIX 43 H18 2 -0.132069 0.585528 -0.408401 11.00000 -1.20000 AFIX 0 C19 1 0.437346 0.656563 0.165089 11.00000 0.05442 0.05678 = 0.05221 0.00628 -0.00064 -0.00442 C20 1 0.421632 0.708117 0.211243 11.00000 0.08391 0.06100 = 0.09100 -0.00090 0.01932 -0.00862 AFIX 43 H20 2 0.337095 0.717311 0.272013 11.00000 -1.20000 AFIX 0 C21 1 0.529352 0.746580 0.168900 11.00000 0.10506 0.06735 = 0.10354 0.00817 0.00581 -0.02162 AFIX 43 H21 2 0.516349 0.781410 0.200191 11.00000 -1.20000 AFIX 0 C22 1 0.653661 0.733534 0.081943 11.00000 0.07911 0.09718 = 0.09353 0.03450 -0.00403 -0.02813 AFIX 43 H22 2 0.724774 0.759579 0.051751 11.00000 -1.20000 AFIX 0 C23 1 0.675237 0.682384 0.038326 11.00000 0.07244 0.11851 = 0.09484 0.02722 0.02696 -0.00602 AFIX 43 H23 2 0.762899 0.673437 -0.018812 11.00000 -1.20000 AFIX 0 C24 1 0.566232 0.643518 0.079192 11.00000 0.07523 0.07671 = 0.07899 0.00574 0.02174 -0.00373 AFIX 43 H24 2 0.580503 0.608694 0.048421 11.00000 -1.20000 AFIX 0 O1 3 -0.057270 0.548898 0.100066 11.00000 0.08786 0.12148 = 0.08533 0.00261 0.00114 -0.04903 O2 3 0.110676 0.536614 0.306688 11.00000 0.08792 0.06923 = 0.06951 0.00342 0.01143 -0.02415 HKLF 4 REM 201803207 in P21/c #14 REM R1 = 0.0492 for 2172 Fo > 4sig(Fo) and 0.0736 for all 3173 data REM 237 parameters refined using 0 restraints END WGHT 0.0684 0.1700 REM Highest difference peak 0.167, deepest hole -0.144, 1-sigma level 0.031 Q1 1 0.2855 0.5058 0.8611 11.00000 0.05 0.17 Q2 1 0.0362 0.5321 0.0798 11.00000 0.05 0.17 Q3 1 0.4904 0.5389 0.9022 11.00000 0.05 0.14 Q4 1 0.5007 0.4773 0.8053 11.00000 0.05 0.13 Q5 1 0.2879 0.5943 0.1396 11.00000 0.05 0.13 Q6 1 0.2859 0.6473 -0.0677 11.00000 0.05 0.12 Q7 1 0.4111 0.6354 0.1842 11.00000 0.05 0.12 Q8 1 0.3707 0.6882 0.1459 11.00000 0.05 0.11 Q9 1 0.3524 0.5218 0.5838 11.00000 0.05 0.11 Q10 1 -0.0592 0.5768 0.1288 11.00000 0.05 0.10 Q11 1 -0.0056 0.5385 0.3697 11.00000 0.05 0.10 Q12 1 0.2396 0.7366 -0.4907 11.00000 0.05 0.10 Q13 1 0.3362 0.5615 0.3705 11.00000 0.05 0.10 Q14 1 0.4680 0.5484 0.6132 11.00000 0.05 0.10 Q15 1 0.5921 0.6974 -0.0256 11.00000 0.05 0.09 Q16 1 0.2213 0.6233 0.1769 11.00000 0.05 0.09 Q17 1 0.0236 0.6102 -0.3661 11.00000 0.05 0.09 Q18 1 0.1620 0.5791 0.1254 11.00000 0.05 0.09 Q19 1 0.5071 0.5973 -0.0218 11.00000 0.05 0.09 Q20 1 0.4303 0.5854 0.3951 11.00000 0.05 0.09 REM The information below was added by Olex2. REM REM R1 = 0.0492 for 2172 Fo > 4sig(Fo) and 0.0736 for all 6674 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.17, deepest hole -0.14 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0736 REM R1_gt = 0.0492 REM wR_ref = 0.1558 REM GOOF = 1.026 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 6674 REM Reflections_gt = 2172 REM Parameters = n/a REM Hole = -0.14 REM Peak = 0.17 REM Flack = n/a ; _cod_data_source_file c9ob00421a2.cif _cod_data_source_block 201803207 _cod_original_cell_volume 1780.67(15) _cod_database_code 7156786 _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 0.923 _shelx_estimated_absorpt_t_min 0.896 _reflns_odcompleteness_completeness 99.79 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _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 2.a Aromatic/amide H refined with riding coordinates: C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24) 2.b Idealised Me refined as rotating group: C10(H10A,H10B,H10C) ; _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 0.0710(3) 0.56161(9) 0.1667(3) 0.0690(6) Uani 1 1 d . C2 C 0.1874(3) 0.60056(7) 0.1139(2) 0.0570(5) Uani 1 1 d . C3 C 0.3184(2) 0.61560(7) 0.2121(2) 0.0535(5) Uani 1 1 d . C4 C 0.3448(3) 0.59247(7) 0.3657(2) 0.0562(5) Uani 1 1 d . C5 C 0.2405(3) 0.55237(8) 0.4073(3) 0.0610(5) Uani 1 1 d . C6 C 0.2605(3) 0.52711(8) 0.5494(3) 0.0687(6) Uani 1 1 d . H6 H 0.1889 0.5003 0.5732 0.082 Uiso 1 1 calc R C7 C 0.3864(3) 0.54161(8) 0.6560(3) 0.0675(6) Uani 1 1 d . C8 C 0.4904(3) 0.58220(9) 0.6174(3) 0.0724(6) Uani 1 1 d . H8 H 0.5748 0.5927 0.6893 0.087 Uiso 1 1 calc R C9 C 0.4711(3) 0.60718(9) 0.4754(3) 0.0663(6) Uani 1 1 d . H9 H 0.5427 0.6341 0.4523 0.080 Uiso 1 1 calc R C10 C 0.4118(4) 0.51424(10) 0.8107(3) 0.0853(8) Uani 1 1 d . H10A H 0.3625 0.5347 0.8883 0.128 Uiso 1 1 calc GR H10B H 0.5270 0.5107 0.8389 0.128 Uiso 1 1 calc GR H10C H 0.3622 0.4799 0.8037 0.128 Uiso 1 1 calc GR C11 C 0.1565(3) 0.62444(8) -0.0398(2) 0.0590(5) Uani 1 1 d . H11 H 0.2224 0.6532 -0.0592 0.071 Uiso 1 1 calc R C12 C 0.0485(3) 0.61125(9) -0.1557(3) 0.0663(6) Uani 1 1 d . H12 H -0.0194 0.5826 -0.1402 0.080 Uiso 1 1 calc R C13 C 0.0274(3) 0.63816(9) -0.3068(3) 0.0620(5) Uani 1 1 d . C14 C 0.1059(3) 0.68499(10) -0.3388(3) 0.0767(7) Uani 1 1 d . H14 H 0.1757 0.7006 -0.2616 0.092 Uiso 1 1 calc R C15 C 0.0832(4) 0.70899(12) -0.4819(3) 0.0902(8) Uani 1 1 d . H15 H 0.1370 0.7405 -0.5000 0.108 Uiso 1 1 calc R C16 C -0.0184(3) 0.68674(12) -0.5985(3) 0.0840(8) Uani 1 1 d . H16 H -0.0330 0.7028 -0.6956 0.101 Uiso 1 1 calc R C17 C -0.0974(3) 0.64076(12) -0.5696(3) 0.0848(8) Uani 1 1 d . H17 H -0.1666 0.6254 -0.6477 0.102 Uiso 1 1 calc R C18 C -0.0761(3) 0.61669(11) -0.4259(3) 0.0781(7) Uani 1 1 d . H18 H -0.1321 0.5855 -0.4084 0.094 Uiso 1 1 calc R C19 C 0.4373(2) 0.65656(8) 0.1651(2) 0.0547(5) Uani 1 1 d . C20 C 0.4216(3) 0.70812(9) 0.2112(3) 0.0780(7) Uani 1 1 d . H20 H 0.3371 0.7173 0.2720 0.094 Uiso 1 1 calc R C21 C 0.5294(4) 0.74658(11) 0.1689(4) 0.0921(8) Uani 1 1 d . H21 H 0.5163 0.7814 0.2002 0.111 Uiso 1 1 calc R C22 C 0.6537(3) 0.73353(12) 0.0819(3) 0.0905(9) Uani 1 1 d . H22 H 0.7248 0.7596 0.0518 0.109 Uiso 1 1 calc R C23 C 0.6752(3) 0.68238(13) 0.0383(4) 0.0942(9) Uani 1 1 d . H23 H 0.7629 0.6734 -0.0188 0.113 Uiso 1 1 calc R C24 C 0.5662(3) 0.64352(10) 0.0792(3) 0.0762(7) Uani 1 1 d . H24 H 0.5805 0.6087 0.0484 0.091 Uiso 1 1 calc R O1 O -0.0573(2) 0.54890(8) 0.1001(2) 0.0985(6) Uani 1 1 d . O2 O 0.1107(2) 0.53661(6) 0.30669(19) 0.0753(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 0.0732(15) 0.0690(13) 0.0656(14) -0.0057(11) 0.0108(11) -0.0182(11) C2 0.0593(12) 0.0526(10) 0.0603(12) -0.0054(9) 0.0126(9) -0.0043(9) C3 0.0552(11) 0.0496(10) 0.0571(11) -0.0010(8) 0.0120(9) -0.0004(8) C4 0.0612(11) 0.0506(10) 0.0580(11) 0.0029(9) 0.0130(9) 0.0008(9) C5 0.0705(13) 0.0521(10) 0.0617(12) -0.0020(9) 0.0142(10) -0.0023(9) C6 0.0863(16) 0.0536(11) 0.0688(14) 0.0069(10) 0.0236(12) -0.0026(11) C7 0.0817(15) 0.0587(12) 0.0641(14) 0.0089(10) 0.0179(11) 0.0119(11) C8 0.0747(15) 0.0771(14) 0.0648(14) 0.0109(11) 0.0019(11) 0.0002(12) C9 0.0657(13) 0.0675(12) 0.0658(13) 0.0104(10) 0.0064(10) -0.0059(10) C10 0.107(2) 0.0782(15) 0.0722(16) 0.0205(13) 0.0188(14) 0.0155(14) C11 0.0580(11) 0.0601(11) 0.0592(12) -0.0061(9) 0.0062(9) -0.0049(9) C12 0.0668(13) 0.0646(12) 0.0678(13) -0.0100(10) 0.0076(11) -0.0105(10) C13 0.0545(11) 0.0720(13) 0.0594(12) -0.0124(10) 0.0046(9) 0.0014(10) C14 0.0833(16) 0.0846(16) 0.0606(14) -0.0034(12) -0.0038(12) -0.0158(13) C15 0.0962(19) 0.106(2) 0.0682(16) 0.0085(14) 0.0034(14) -0.0076(16) C16 0.0727(15) 0.120(2) 0.0597(14) -0.0019(14) 0.0050(12) 0.0197(15) C17 0.0648(14) 0.121(2) 0.0660(15) -0.0224(15) -0.0100(11) 0.0110(15) C18 0.0667(14) 0.0905(17) 0.0758(16) -0.0172(13) -0.0036(12) -0.0062(12) C19 0.0544(11) 0.0568(10) 0.0522(10) 0.0063(9) -0.0006(8) -0.0044(9) C20 0.0839(16) 0.0610(13) 0.0910(18) -0.0009(12) 0.0193(14) -0.0086(12) C21 0.105(2) 0.0674(15) 0.104(2) 0.0082(14) 0.0058(18) -0.0216(15) C22 0.0791(17) 0.097(2) 0.094(2) 0.0345(16) -0.0040(15) -0.0281(15) C23 0.0724(16) 0.119(2) 0.095(2) 0.0272(18) 0.0270(15) -0.0060(16) C24 0.0752(15) 0.0767(15) 0.0790(16) 0.0057(12) 0.0217(12) -0.0037(12) O1 0.0879(12) 0.1215(15) 0.0853(13) 0.0026(11) 0.0011(10) -0.0490(11) O2 0.0879(11) 0.0692(9) 0.0695(10) 0.0034(8) 0.0114(8) -0.0241(8) 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 126.6(2) O1 C1 O2 115.7(2) O2 C1 C2 117.7(2) C3 C2 C1 119.5(2) C3 C2 C11 121.25(18) C11 C2 C1 119.22(19) C2 C3 C4 120.48(18) C2 C3 C19 121.31(18) C4 C3 C19 118.21(17) C5 C4 C3 118.7(2) C5 C4 C9 117.2(2) C9 C4 C3 124.13(19) C6 C5 C4 122.3(2) O2 C5 C4 120.5(2) O2 C5 C6 117.2(2) C5 C6 H6 120.0 C7 C6 C5 120.0(2) C7 C6 H6 120.0 C6 C7 C8 118.6(2) C6 C7 C10 120.9(2) C8 C7 C10 120.5(2) C7 C8 H8 119.3 C9 C8 C7 121.4(2) C9 C8 H8 119.3 C4 C9 H9 119.7 C8 C9 C4 120.5(2) C8 C9 H9 119.7 C7 C10 H10A 109.5 C7 C10 H10B 109.5 C7 C10 H10C 109.5 H10A C10 H10B 109.5 H10A C10 H10C 109.5 H10B C10 H10C 109.5 C2 C11 H11 115.1 C12 C11 C2 129.7(2) C12 C11 H11 115.1 C11 C12 H12 117.3 C11 C12 C13 125.3(2) C13 C12 H12 117.3 C14 C13 C12 123.3(2) C14 C13 C18 116.9(2) C18 C13 C12 119.8(2) C13 C14 H14 119.2 C15 C14 C13 121.6(2) C15 C14 H14 119.2 C14 C15 H15 119.8 C16 C15 C14 120.5(3) C16 C15 H15 119.8 C15 C16 H16 120.5 C17 C16 C15 119.0(3) C17 C16 H16 120.5 C16 C17 H17 119.6 C16 C17 C18 120.8(2) C18 C17 H17 119.6 C13 C18 H18 119.4 C17 C18 C13 121.2(3) C17 C18 H18 119.4 C20 C19 C3 120.04(19) C20 C19 C24 118.5(2) C24 C19 C3 121.44(19) C19 C20 H20 119.5 C19 C20 C21 121.1(3) C21 C20 H20 119.5 C20 C21 H21 120.0 C22 C21 C20 119.9(3) C22 C21 H21 120.0 C21 C22 H22 119.9 C21 C22 C23 120.3(3) C23 C22 H22 119.9 C22 C23 H23 120.0 C22 C23 C24 120.1(3) C24 C23 H23 120.0 C19 C24 C23 120.1(2) C19 C24 H24 120.0 C23 C24 H24 120.0 C5 O2 C1 122.42(17) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.468(3) C1 O1 1.201(3) C1 O2 1.379(3) C2 C3 1.368(3) C2 C11 1.460(3) C3 C4 1.448(3) C3 C19 1.500(3) C4 C5 1.391(3) C4 C9 1.396(3) C5 C6 1.380(3) C5 O2 1.378(3) C6 H6 0.9300 C6 C7 1.376(3) C7 C8 1.391(3) C7 C10 1.503(3) C8 H8 0.9300 C8 C9 1.376(3) C9 H9 0.9300 C10 H10A 0.9600 C10 H10B 0.9600 C10 H10C 0.9600 C11 H11 0.9300 C11 C12 1.324(3) C12 H12 0.9300 C12 C13 1.468(3) C13 C14 1.386(3) C13 C18 1.390(3) C14 H14 0.9300 C14 C15 1.374(3) C15 H15 0.9300 C15 C16 1.374(4) C16 H16 0.9300 C16 C17 1.364(4) C17 H17 0.9300 C17 C18 1.378(4) C18 H18 0.9300 C19 C20 1.372(3) C19 C24 1.376(3) C20 H20 0.9300 C20 C21 1.382(3) C21 H21 0.9300 C21 C22 1.352(4) C22 H22 0.9300 C22 C23 1.363(4) C23 H23 0.9300 C23 C24 1.392(3) C24 H24 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 1.5(3) C1 C2 C3 C19 -177.95(18) C1 C2 C11 C12 -11.3(3) C2 C1 O2 C5 9.9(3) C2 C3 C4 C5 4.0(3) C2 C3 C4 C9 -177.1(2) C2 C3 C19 C20 97.5(3) C2 C3 C19 C24 -84.3(3) C2 C11 C12 C13 180.0(2) C3 C2 C11 C12 171.8(2) C3 C4 C5 C6 177.88(19) C3 C4 C5 O2 -2.7(3) C3 C4 C9 C8 -178.2(2) C3 C19 C20 C21 -179.8(2) C3 C19 C24 C23 -179.5(2) C4 C3 C19 C20 -81.9(3) C4 C3 C19 C24 96.3(2) C4 C5 C6 C7 0.4(3) C4 C5 O2 C1 -4.5(3) C5 C4 C9 C8 0.6(3) C5 C6 C7 C8 0.6(3) C5 C6 C7 C10 -179.3(2) C6 C5 O2 C1 174.9(2) C6 C7 C8 C9 -1.0(4) C7 C8 C9 C4 0.4(4) C9 C4 C5 C6 -1.0(3) C9 C4 C5 O2 178.38(19) C10 C7 C8 C9 178.9(2) C11 C2 C3 C4 178.39(17) C11 C2 C3 C19 -1.0(3) C11 C12 C13 C14 -8.1(4) C11 C12 C13 C18 172.1(2) C12 C13 C14 C15 179.9(2) C12 C13 C18 C17 -179.4(2) C13 C14 C15 C16 -0.4(4) C14 C13 C18 C17 0.8(4) C14 C15 C16 C17 0.6(4) C15 C16 C17 C18 -0.1(4) C16 C17 C18 C13 -0.6(4) C18 C13 C14 C15 -0.3(4) C19 C3 C4 C5 -176.52(18) C19 C3 C4 C9 2.3(3) C19 C20 C21 C22 -0.7(4) C20 C19 C24 C23 -1.3(4) C20 C21 C22 C23 -1.3(5) C21 C22 C23 C24 2.0(5) C22 C23 C24 C19 -0.7(4) C24 C19 C20 C21 1.9(4) O1 C1 C2 C3 171.8(2) O1 C1 C2 C11 -5.2(4) O1 C1 O2 C5 -170.1(2) O2 C1 C2 C3 -8.3(3) O2 C1 C2 C11 174.73(18) O2 C5 C6 C7 -179.02(19)