#------------------------------------------------------------------------------ #$Date: 2019-04-19 03:55:33 +0300 (Fri, 19 Apr 2019) $ #$Revision: 214701 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/67/7156787.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_7156787 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 'C25 H20 O3' _chemical_formula_sum 'C25 H20 O3' _chemical_formula_weight 368.41 _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 iterative _audit_creation_date 2018-09-18 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2018-10-08 deposited with the CCDC. 2019-04-16 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.176(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.2348(12) _cell_length_b 6.8428(7) _cell_length_c 23.447(2) _cell_measurement_reflns_used 1079 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 70.3270 _cell_measurement_theta_min 4.8080 _cell_volume 1932.1(3) _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 ; Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012) ; _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 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -102.00 -20.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -33.5000 -57.0000 -120.0000 82 #__ type_ start__ end____ width___ exp.time_ 2 omega -101.00 -16.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -33.5000 -57.0000 -30.0000 85 #__ type_ start__ end____ width___ exp.time_ 3 omega 65.00 96.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 178.0000 -180.0000 31 #__ type_ start__ end____ width___ exp.time_ 4 omega 82.00 107.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 37.0000 -90.0000 25 #__ type_ start__ end____ width___ exp.time_ 5 omega 59.00 85.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 178.0000 -150.0000 26 #__ type_ start__ end____ width___ exp.time_ 6 omega 18.00 77.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 37.0000 -90.0000 59 #__ type_ start__ end____ width___ exp.time_ 7 omega -1.00 99.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 19.0000 30.0000 100 #__ type_ start__ end____ width___ exp.time_ 8 omega 22.00 74.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 -99.0000 30.0000 52 #__ type_ start__ end____ width___ exp.time_ 9 omega 57.00 84.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 -120.0000 27 #__ type_ start__ end____ width___ exp.time_ 10 omega 58.00 89.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -94.0000 30.0000 31 #__ type_ start__ end____ width___ exp.time_ 11 omega 38.00 87.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 60.0000 49 #__ type_ start__ end____ width___ exp.time_ 12 omega 122.00 178.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 45.0000 -120.0000 56 #__ type_ start__ end____ width___ exp.time_ 13 omega 38.00 90.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -45.0000 -60.0000 52 #__ type_ start__ end____ width___ exp.time_ 14 omega 107.00 148.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 90.0000 41 #__ type_ start__ end____ width___ exp.time_ 15 omega 55.00 90.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 150.0000 35 #__ type_ start__ end____ width___ exp.time_ 16 omega 44.00 73.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -24.0000 117.0000 29 #__ type_ start__ end____ width___ exp.time_ 17 omega 50.00 90.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 -30.0000 40 #__ type_ start__ end____ width___ exp.time_ 18 omega 38.00 99.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -45.0000 120.0000 61 #__ type_ start__ end____ width___ exp.time_ 19 omega 79.00 148.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 178.0000 -180.0000 69 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.1151784000 _diffrn_orient_matrix_UB_12 0.0653381000 _diffrn_orient_matrix_UB_13 -0.0107024000 _diffrn_orient_matrix_UB_21 -0.0465912000 _diffrn_orient_matrix_UB_22 0.0228407000 _diffrn_orient_matrix_UB_23 -0.0651038000 _diffrn_orient_matrix_UB_31 -0.0302001000 _diffrn_orient_matrix_UB_32 0.2142691000 _diffrn_orient_matrix_UB_33 0.0101708000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_unetI/netI 0.0374 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 7182 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 67.080 _diffrn_reflns_theta_max 67.080 _diffrn_reflns_theta_min 3.670 _diffrn_source 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.657 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.91509 _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 1.266 _exptl_crystal_description needle _exptl_crystal_F_000 776 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _refine_diff_density_max 0.461 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.063 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 255 _refine_ls_number_reflns 3445 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.021 _refine_ls_R_factor_all 0.1232 _refine_ls_R_factor_gt 0.0783 _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^)+(0.1497P)^2^+0.0558P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2180 _refine_ls_wR_factor_ref 0.2779 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1880 _reflns_number_total 3445 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; 201809374a.res created by SHELXL-2014/7 TITL CF solution in P21/c CELL 1.54184 12.234798 6.842752 23.447358 90 100.1757 90 ZERR 4 0.001218 0.000664 0.002202 0 0.0093 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H O UNIT 100 80 12 L.S. 4 0 0 PLAN 20 SIZE 0.09 0.12 0.26 MPLA C1 C2 C3 C4 C5 O2 MPLA C4 C5 C6 C7 C8 C9 MPLA C11 C12 C13 C14 C15 C16 MPLA C19 C20 C21 C22 C23 C24 BOND $h conf fmap 2 acta REM REM REM WGHT 0.149700 0.055800 FVAR 2.87745 C1 1 -0.103980 0.750361 0.501234 11.00000 0.05222 0.04476 = 0.04397 -0.00132 0.01317 -0.00134 C2 1 -0.023094 0.742354 0.461067 11.00000 0.05130 0.03962 = 0.03997 -0.00047 0.01235 0.00021 C3 1 -0.060739 0.732681 0.402746 11.00000 0.04859 0.04363 = 0.04155 -0.00073 0.01392 -0.00037 C4 1 -0.178826 0.734198 0.379860 11.00000 0.05010 0.04453 = 0.04381 0.00215 0.01060 -0.00096 C5 1 -0.253131 0.743632 0.418424 11.00000 0.05333 0.04324 = 0.04570 0.00175 0.01080 0.00030 C6 1 -0.366821 0.747228 0.400532 11.00000 0.05096 0.05797 = 0.05829 0.00111 0.01848 -0.00058 AFIX 43 H6 2 -0.413432 0.751438 0.427836 11.00000 -1.20000 AFIX 0 C7 1 -0.411194 0.744607 0.342582 11.00000 0.04875 0.06186 = 0.05963 0.00202 0.00655 -0.00072 C8 1 -0.338644 0.736503 0.302588 11.00000 0.05646 0.07423 = 0.04728 0.00093 0.00280 -0.00640 AFIX 43 H8 2 -0.367486 0.734493 0.263141 11.00000 -1.20000 AFIX 0 C9 1 -0.225905 0.731495 0.320693 11.00000 0.05939 0.06574 = 0.04271 0.00424 0.01250 -0.00366 AFIX 43 H9 2 -0.179590 0.726200 0.293262 11.00000 -1.20000 AFIX 0 C10 1 -0.535272 0.748773 0.322532 11.00000 0.05204 0.10203 = 0.07603 0.00468 0.00771 -0.00041 AFIX 137 H10A 2 -0.567778 0.634513 0.336439 11.00000 -1.50000 H10B 2 -0.551522 0.750896 0.280956 11.00000 -1.50000 H10C 2 -0.565502 0.863561 0.337438 11.00000 -1.50000 AFIX 0 C11 1 0.016901 0.719719 0.360479 11.00000 0.04496 0.07194 = 0.03390 -0.00176 0.00715 0.00371 C12 1 0.021778 0.544923 0.329791 11.00000 0.08321 0.08138 = 0.06635 -0.01320 0.02292 0.00865 AFIX 43 H12 2 -0.022174 0.439240 0.336340 11.00000 -1.20000 AFIX 0 C13 1 0.091554 0.529863 0.290023 11.00000 0.08794 0.13873 = 0.07225 -0.02925 0.02431 0.02813 AFIX 43 H13 2 0.093366 0.415076 0.268973 11.00000 -1.20000 AFIX 0 C14 1 0.159216 0.685487 0.281246 11.00000 0.06401 0.19945 = 0.05419 -0.00898 0.02247 0.02275 AFIX 43 H14 2 0.207203 0.674562 0.254756 11.00000 -1.20000 AFIX 0 C15 1 0.155269 0.852338 0.311150 11.00000 0.06819 0.16412 = 0.06862 0.00879 0.02601 -0.02203 AFIX 43 H15 2 0.200691 0.956562 0.305147 11.00000 -1.20000 AFIX 0 C16 1 0.083799 0.870736 0.351061 11.00000 0.07056 0.10294 = 0.05840 -0.00626 0.02281 -0.01214 AFIX 43 H16 2 0.081867 0.987054 0.371374 11.00000 -1.20000 AFIX 0 C17 1 0.094247 0.738820 0.485665 11.00000 0.05437 0.04946 = 0.04118 0.00135 0.01093 0.00037 AFIX 43 H17 2 0.141050 0.719599 0.458933 11.00000 -1.20000 AFIX 0 C18 1 0.145578 0.758483 0.539942 11.00000 0.05740 0.04872 = 0.04037 -0.00016 0.01044 0.00245 AFIX 43 H18 2 0.100497 0.776132 0.567576 11.00000 -1.20000 AFIX 0 C19 1 0.264908 0.755573 0.561262 11.00000 0.05596 0.04559 = 0.04460 -0.00085 0.00812 0.00007 C20 1 0.344680 0.752304 0.525454 11.00000 0.06274 0.08566 = 0.03818 0.00045 0.01058 -0.00183 AFIX 43 H20 2 0.321555 0.752827 0.485479 11.00000 -1.20000 AFIX 0 C21 1 0.457876 0.748282 0.547863 11.00000 0.06258 0.09617 = 0.05119 -0.00024 0.02429 -0.00001 AFIX 43 H21 2 0.509226 0.745927 0.522980 11.00000 -1.20000 AFIX 0 C22 1 0.493790 0.747794 0.607111 11.00000 0.05488 0.06633 = 0.05134 -0.00130 0.00874 -0.00322 C23 1 0.415283 0.754056 0.643432 11.00000 0.05834 0.07641 = 0.03761 0.00029 0.00363 -0.00367 AFIX 43 H23 2 0.438603 0.754830 0.683393 11.00000 -1.20000 AFIX 0 C24 1 0.303534 0.759113 0.620853 11.00000 0.05986 0.06118 = 0.04159 -0.00072 0.01324 0.00009 AFIX 43 H24 2 0.252632 0.765029 0.645939 11.00000 -1.20000 AFIX 0 C25 1 0.684354 0.730439 0.597590 11.00000 0.05405 0.15235 = 0.09245 -0.00592 0.02126 -0.00568 AFIX 137 H25A 2 0.677174 0.840406 0.571773 11.00000 -1.50000 H25B 2 0.674174 0.611768 0.575449 11.00000 -1.50000 H25C 2 0.756938 0.730926 0.621211 11.00000 -1.50000 AFIX 0 O1 3 -0.082870 0.755256 0.553096 11.00000 0.06449 0.08141 = 0.03734 -0.00078 0.01524 0.00262 O2 3 -0.215229 0.749088 0.477097 11.00000 0.05290 0.06045 = 0.04110 -0.00070 0.01602 0.00061 O3 3 0.602081 0.742681 0.633850 11.00000 0.05407 0.11940 = 0.06283 -0.00210 0.00621 -0.00190 HKLF 4 REM CF solution in P21/c REM R1 = 0.0783 for 1880 Fo > 4sig(Fo) and 0.1232 for all 3445 data REM 255 parameters refined using 0 restraints END WGHT 0.1497 0.0558 REM Highest difference peak 0.461, deepest hole -0.232, 1-sigma level 0.063 Q1 1 0.0186 0.9651 0.3304 11.00000 0.05 0.46 Q2 1 0.0852 0.6171 0.3547 11.00000 0.05 0.44 Q3 1 0.1589 0.6208 0.3137 11.00000 0.05 0.42 Q4 1 0.0844 0.9828 0.2902 11.00000 0.05 0.41 Q5 1 0.1336 0.8415 0.2756 11.00000 0.05 0.21 Q6 1 -0.5538 0.9090 0.2941 11.00000 0.05 0.20 Q7 1 -0.5599 0.5947 0.2978 11.00000 0.05 0.20 Q8 1 -0.2283 0.9265 0.4749 11.00000 0.05 0.17 Q9 1 -0.2444 0.5667 0.4981 11.00000 0.05 0.17 Q10 1 0.2791 0.5737 0.6423 11.00000 0.05 0.16 Q11 1 0.3151 0.8147 0.5417 11.00000 0.05 0.15 Q12 1 0.0272 0.7831 0.3612 11.00000 0.05 0.15 Q13 1 0.3424 0.5469 0.5450 11.00000 0.05 0.15 Q14 1 0.0949 0.9725 0.6117 11.00000 0.05 0.15 Q15 1 0.1013 0.4964 0.1862 11.00000 0.05 0.14 Q16 1 0.6542 0.9288 0.5558 11.00000 0.05 0.14 Q17 1 0.2641 0.9640 0.4650 11.00000 0.05 0.14 Q18 1 0.1031 1.0251 0.3810 11.00000 0.05 0.14 Q19 1 0.6441 1.0463 0.5837 11.00000 0.05 0.13 Q20 1 -0.5686 0.7983 0.3657 11.00000 0.05 0.13 REM The information below was added by Olex2. REM REM R1 = 0.0783 for 1880 Fo > 4sig(Fo) and 0.1232 for all 7644 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.46, deepest hole -0.23 REM Mean Shift 0, Max Shift -0.001. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.1232 REM R1_gt = 0.0783 REM wR_ref = 0.2779 REM GOOF = 1.021 REM Shift_max = -0.001 REM Shift_mean = 0 REM Reflections_all = 7644 REM Reflections_gt = 1880 REM Parameters = n/a REM Hole = -0.23 REM Peak = 0.46 REM Flack = n/a ; _cod_data_source_file c9ob00421a2.cif _cod_data_source_block 201809374a _cod_database_code 7156787 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_formula C15H15O3N2Cl1 _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 0.943 _shelx_estimated_absorpt_t_min 0.848 _reflns_odcompleteness_completeness 99.87 _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), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24) 2.b Idealised Me refined as rotating group: C10(H10A,H10B,H10C), C25(H25A,H25B,H25C) ; _olex2_date_sample_data_collection 1537181979.33 _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 -0.1040(3) 0.7504(4) 0.50123(13) 0.0464(7) Uani 1 1 d . C2 C -0.0231(2) 0.7424(4) 0.46107(12) 0.0431(7) Uani 1 1 d . C3 C -0.0607(2) 0.7327(4) 0.40275(12) 0.0439(7) Uani 1 1 d . C4 C -0.1788(3) 0.7342(4) 0.37986(13) 0.0459(7) Uani 1 1 d . C5 C -0.2531(3) 0.7436(4) 0.41842(13) 0.0472(7) Uani 1 1 d . C6 C -0.3668(3) 0.7472(4) 0.40053(15) 0.0547(8) Uani 1 1 d . H6 H -0.4134 0.7514 0.4278 0.066 Uiso 1 1 calc R C7 C -0.4112(3) 0.7446(5) 0.34258(15) 0.0571(8) Uani 1 1 d . C8 C -0.3386(3) 0.7365(5) 0.30259(14) 0.0601(9) Uani 1 1 d . H8 H -0.3675 0.7345 0.2631 0.072 Uiso 1 1 calc R C9 C -0.2259(3) 0.7315(4) 0.32069(13) 0.0555(8) Uani 1 1 d . H9 H -0.1796 0.7262 0.2933 0.067 Uiso 1 1 calc R C10 C -0.5353(3) 0.7488(6) 0.32253(19) 0.0771(11) Uani 1 1 d . H10A H -0.5678 0.6345 0.3364 0.116 Uiso 1 1 calc GR H10B H -0.5515 0.7509 0.2810 0.116 Uiso 1 1 calc GR H10C H -0.5655 0.8636 0.3374 0.116 Uiso 1 1 calc GR C11 C 0.0169(2) 0.7197(5) 0.36048(12) 0.0502(8) Uani 1 1 d . C12 C 0.0218(3) 0.5449(6) 0.32979(15) 0.0758(11) Uani 1 1 d . H12 H -0.0222 0.4392 0.3363 0.091 Uiso 1 1 calc R C13 C 0.0916(4) 0.5299(9) 0.29002(18) 0.0984(16) Uani 1 1 d . H13 H 0.0934 0.4151 0.2690 0.118 Uiso 1 1 calc R C14 C 0.1592(4) 0.6855(10) 0.28125(18) 0.1044(19) Uani 1 1 d . H14 H 0.2072 0.6746 0.2548 0.125 Uiso 1 1 calc R C15 C 0.1553(4) 0.8523(9) 0.31115(19) 0.0986(16) Uani 1 1 d . H15 H 0.2007 0.9566 0.3051 0.118 Uiso 1 1 calc R C16 C 0.0838(3) 0.8707(7) 0.35106(15) 0.0759(11) Uani 1 1 d . H16 H 0.0819 0.9871 0.3714 0.091 Uiso 1 1 calc R C17 C 0.0942(3) 0.7388(4) 0.48566(13) 0.0480(7) Uani 1 1 d . H17 H 0.1411 0.7196 0.4589 0.058 Uiso 1 1 calc R C18 C 0.1456(3) 0.7585(4) 0.53994(13) 0.0486(7) Uani 1 1 d . H18 H 0.1005 0.7761 0.5676 0.058 Uiso 1 1 calc R C19 C 0.2649(3) 0.7556(4) 0.56126(13) 0.0488(7) Uani 1 1 d . C20 C 0.3447(3) 0.7523(5) 0.52545(14) 0.0620(9) Uani 1 1 d . H20 H 0.3216 0.7528 0.4855 0.074 Uiso 1 1 calc R C21 C 0.4579(3) 0.7483(5) 0.54786(15) 0.0682(10) Uani 1 1 d . H21 H 0.5092 0.7459 0.5230 0.082 Uiso 1 1 calc R C22 C 0.4938(3) 0.7478(5) 0.60711(14) 0.0576(8) Uani 1 1 d . C23 C 0.4153(3) 0.7541(5) 0.64343(13) 0.0580(9) Uani 1 1 d . H23 H 0.4386 0.7548 0.6834 0.070 Uiso 1 1 calc R C24 C 0.3035(3) 0.7591(4) 0.62085(13) 0.0537(8) Uani 1 1 d . H24 H 0.2526 0.7650 0.6459 0.064 Uiso 1 1 calc R C25 C 0.6844(3) 0.7304(7) 0.5976(2) 0.0986(16) Uani 1 1 d . H25A H 0.6772 0.8404 0.5718 0.148 Uiso 1 1 calc GR H25B H 0.6742 0.6118 0.5754 0.148 Uiso 1 1 calc GR H25C H 0.7569 0.7309 0.6212 0.148 Uiso 1 1 calc GR O1 O -0.0829(2) 0.7553(3) 0.55310(9) 0.0603(7) Uani 1 1 d . O2 O -0.21523(18) 0.7491(3) 0.47710(9) 0.0505(6) Uani 1 1 d . O3 O 0.6021(2) 0.7427(4) 0.63385(11) 0.0793(9) 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 0.0522(17) 0.0448(16) 0.0440(16) -0.0013(12) 0.0132(12) -0.0013(14) C2 0.0513(17) 0.0396(14) 0.0400(15) -0.0005(11) 0.0124(12) 0.0002(12) C3 0.0486(16) 0.0436(15) 0.0416(14) -0.0007(12) 0.0139(12) -0.0004(13) C4 0.0501(16) 0.0445(15) 0.0438(15) 0.0022(12) 0.0106(12) -0.0010(13) C5 0.0533(17) 0.0432(15) 0.0457(15) 0.0017(12) 0.0108(12) 0.0003(13) C6 0.0510(17) 0.0580(19) 0.0583(19) 0.0011(14) 0.0185(14) -0.0006(15) C7 0.0487(17) 0.062(2) 0.0596(19) 0.0020(15) 0.0066(14) -0.0007(15) C8 0.0565(18) 0.074(2) 0.0473(17) 0.0009(15) 0.0028(14) -0.0064(17) C9 0.0594(18) 0.066(2) 0.0427(16) 0.0042(14) 0.0125(13) -0.0037(16) C10 0.052(2) 0.102(3) 0.076(2) 0.005(2) 0.0077(17) 0.000(2) C11 0.0450(15) 0.072(2) 0.0339(13) -0.0018(13) 0.0072(11) 0.0037(15) C12 0.083(3) 0.081(3) 0.066(2) -0.0132(19) 0.0229(19) 0.009(2) C13 0.088(3) 0.139(4) 0.072(3) -0.029(3) 0.024(2) 0.028(3) C14 0.064(2) 0.199(6) 0.054(2) -0.009(3) 0.0225(19) 0.023(3) C15 0.068(3) 0.164(5) 0.069(3) 0.009(3) 0.026(2) -0.022(3) C16 0.071(2) 0.103(3) 0.058(2) -0.006(2) 0.0228(17) -0.012(2) C17 0.0544(18) 0.0495(17) 0.0412(15) 0.0014(12) 0.0109(13) 0.0004(14) C18 0.0574(18) 0.0487(17) 0.0404(15) -0.0002(12) 0.0104(13) 0.0024(14) C19 0.0560(17) 0.0456(16) 0.0446(16) -0.0008(12) 0.0081(13) 0.0001(14) C20 0.063(2) 0.086(3) 0.0382(15) 0.0004(15) 0.0106(13) -0.0018(18) C21 0.063(2) 0.096(3) 0.0512(19) -0.0002(17) 0.0243(15) 0.0000(19) C22 0.0549(18) 0.066(2) 0.0513(17) -0.0013(15) 0.0087(14) -0.0032(17) C23 0.0583(19) 0.076(2) 0.0376(15) 0.0003(15) 0.0036(13) -0.0037(17) C24 0.0599(19) 0.0612(19) 0.0416(15) -0.0007(13) 0.0132(13) 0.0001(15) C25 0.054(2) 0.152(5) 0.092(3) -0.006(3) 0.021(2) -0.006(2) O1 0.0645(14) 0.0814(16) 0.0373(11) -0.0008(10) 0.0152(9) 0.0026(12) O2 0.0529(12) 0.0604(13) 0.0411(11) -0.0007(9) 0.0160(8) 0.0006(10) O3 0.0541(15) 0.119(2) 0.0628(16) -0.0021(14) 0.0062(11) -0.0019(14) 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 126.7(3) O1 C1 O2 115.9(3) O2 C1 C2 117.4(3) C3 C2 C1 119.5(3) C3 C2 C17 122.2(3) C17 C2 C1 118.2(3) C2 C3 C4 120.5(3) C2 C3 C11 121.8(3) C4 C3 C11 117.7(3) C5 C4 C3 118.8(3) C5 C4 C9 116.2(3) C9 C4 C3 125.0(3) C6 C5 C4 122.8(3) O2 C5 C4 120.6(3) O2 C5 C6 116.6(3) C5 C6 H6 119.9 C7 C6 C5 120.1(3) C7 C6 H6 119.9 C6 C7 C8 118.5(3) C6 C7 C10 120.6(3) C8 C7 C10 120.9(3) C7 C8 H8 119.5 C9 C8 C7 121.0(3) C9 C8 H8 119.5 C4 C9 H9 119.3 C8 C9 C4 121.3(3) C8 C9 H9 119.3 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 C12 C11 C3 118.8(3) C16 C11 C3 122.3(3) C16 C11 C12 118.9(3) C11 C12 H12 120.0 C13 C12 C11 120.0(4) C13 C12 H12 120.0 C12 C13 H13 119.9 C12 C13 C14 120.1(4) C14 C13 H13 119.9 C13 C14 H14 120.1 C15 C14 C13 119.8(4) C15 C14 H14 120.1 C14 C15 H15 119.6 C14 C15 C16 120.7(5) C16 C15 H15 119.6 C11 C16 C15 120.5(4) C11 C16 H16 119.8 C15 C16 H16 119.8 C2 C17 H17 114.7 C18 C17 C2 130.5(3) C18 C17 H17 114.7 C17 C18 H18 116.4 C17 C18 C19 127.2(3) C19 C18 H18 116.4 C20 C19 C18 124.0(3) C24 C19 C18 119.0(3) C24 C19 C20 117.0(3) C19 C20 H20 119.1 C21 C20 C19 121.9(3) C21 C20 H20 119.1 C20 C21 H21 120.1 C22 C21 C20 119.9(3) C22 C21 H21 120.1 C21 C22 C23 118.9(3) O3 C22 C21 125.0(3) O3 C22 C23 116.1(3) C22 C23 H23 119.6 C24 C23 C22 120.7(3) C24 C23 H23 119.6 C19 C24 H24 119.2 C23 C24 C19 121.5(3) C23 C24 H24 119.2 H25A C25 H25B 109.5 H25A C25 H25C 109.5 H25B C25 H25C 109.5 O3 C25 H25A 109.5 O3 C25 H25B 109.5 O3 C25 H25C 109.5 C5 O2 C1 123.1(2) C22 O3 C25 117.2(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.483(4) C1 O1 1.198(4) C1 O2 1.379(4) C2 C3 1.365(4) C2 C17 1.450(4) C3 C4 1.450(4) C3 C11 1.492(4) C4 C5 1.392(4) C4 C9 1.405(4) C5 C6 1.380(4) C5 O2 1.372(4) C6 H6 0.9300 C6 C7 1.371(5) C7 C8 1.402(5) C7 C10 1.508(4) C8 H8 0.9300 C8 C9 1.370(5) C9 H9 0.9300 C10 H10A 0.9600 C10 H10B 0.9600 C10 H10C 0.9600 C11 C12 1.403(5) C11 C16 1.360(5) C12 H12 0.9300 C12 C13 1.375(5) C13 H13 0.9300 C13 C14 1.386(7) C14 H14 0.9300 C14 C15 1.345(8) C15 H15 0.9300 C15 C16 1.395(5) C16 H16 0.9300 C17 H17 0.9300 C17 C18 1.323(4) C18 H18 0.9300 C18 C19 1.457(4) C19 C20 1.396(5) C19 C24 1.394(4) C20 H20 0.9300 C20 C21 1.392(5) C21 H21 0.9300 C21 C22 1.381(5) C22 C23 1.392(5) C22 O3 1.362(4) C23 H23 0.9300 C23 C24 1.377(5) C24 H24 0.9300 C25 H25A 0.9600 C25 H25B 0.9600 C25 H25C 0.9600 C25 O3 1.430(5) 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 1.3(4) C1 C2 C3 C11 -178.6(3) C1 C2 C17 C18 -6.6(5) C2 C1 O2 C5 -0.9(4) C2 C3 C4 C5 -0.7(4) C2 C3 C4 C9 177.7(3) C2 C3 C11 C12 110.8(3) C2 C3 C11 C16 -68.6(4) C2 C17 C18 C19 -179.2(3) C3 C2 C17 C18 175.4(3) C3 C4 C5 C6 179.5(3) C3 C4 C5 O2 -0.8(4) C3 C4 C9 C8 -178.9(3) C3 C11 C12 C13 179.2(3) C3 C11 C16 C15 180.0(4) C4 C3 C11 C12 -69.1(4) C4 C3 C11 C16 111.6(3) C4 C5 C6 C7 -1.0(5) C4 C5 O2 C1 1.6(4) C5 C4 C9 C8 -0.5(4) C5 C6 C7 C8 0.6(5) C5 C6 C7 C10 -179.9(3) C6 C5 O2 C1 -178.7(3) C6 C7 C8 C9 -0.1(5) C7 C8 C9 C4 0.0(5) C9 C4 C5 C6 1.0(4) C9 C4 C5 O2 -179.3(3) C10 C7 C8 C9 -179.6(3) C11 C3 C4 C5 179.2(3) C11 C3 C4 C9 -2.4(4) C11 C12 C13 C14 1.6(6) C12 C11 C16 C15 0.6(5) C12 C13 C14 C15 -1.0(7) C13 C14 C15 C16 0.1(7) C14 C15 C16 C11 0.1(7) C16 C11 C12 C13 -1.4(5) C17 C2 C3 C4 179.2(2) C17 C2 C3 C11 -0.6(4) C17 C18 C19 C20 7.4(5) C17 C18 C19 C24 -173.6(3) C18 C19 C20 C21 -179.6(3) C18 C19 C24 C23 179.1(3) C19 C20 C21 C22 -0.1(5) C20 C19 C24 C23 -1.8(5) C20 C21 C22 C23 -0.9(5) C20 C21 C22 O3 179.5(3) C21 C22 C23 C24 0.5(5) C21 C22 O3 C25 -2.2(5) C22 C23 C24 C19 0.9(5) C23 C22 O3 C25 178.2(3) C24 C19 C20 C21 1.4(5) O1 C1 C2 C3 178.4(3) O1 C1 C2 C17 0.4(4) O1 C1 O2 C5 -180.0(2) O2 C1 C2 C3 -0.5(4) O2 C1 C2 C17 -178.5(2) O2 C5 C6 C7 179.2(3) O3 C22 C23 C24 -179.9(3)