#------------------------------------------------------------------------------ #$Date: 2021-07-29 04:50:48 +0300 (Thu, 29 Jul 2021) $ #$Revision: 267794 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/42/1564261.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_1564261 loop_ _publ_author_name 'Guo, Wengang' 'Wang, Min' 'Han, Zhengyu' 'Huang, Hai' 'Sun, Jianwei' _publ_section_title ; Organocatalytic asymmetric synthesis of \a-amino esters from sulfoxonium ylides ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D1SC02439F _journal_year 2021 _chemical_absolute_configuration ad _chemical_formula_moiety 'C21 H19 N O3' _chemical_formula_sum 'C21 H19 N O3' _chemical_formula_weight 333.37 _chemical_name_systematic 'Phenyl (S)-2-((4-methoxyphenyl)amino)-2-phenylacetate' _space_group_crystal_system monoclinic _space_group_IT_number 5 _space_group_name_Hall 'C 2y' _space_group_name_H-M_alt 'C 1 2 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2020-11-20 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2021-04-29 deposited with the CCDC. 2021-06-29 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 94.888(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 20.2280(4) _cell_length_b 7.9448(2) _cell_length_c 10.7105(2) _cell_measurement_reflns_used 3471 _cell_measurement_temperature 99.93(17) _cell_measurement_theta_max 72.3690 _cell_measurement_theta_min 4.3790 _cell_volume 1715.00(6) _computing_cell_refinement 'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)' _computing_data_collection 'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)' _computing_data_reduction 'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)' _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_environment N~2~ _diffrn_ambient_temperature 99.93(17) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.1788 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.969 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 80.00 173.00 1.00 10.00 -- 104.18 30.00 -90.00 93 2 \w -109.00 -15.00 1.00 4.00 -- -40.20 -37.00-120.00 94 3 \w -64.00 30.00 1.00 4.00 -- -40.20 37.00 60.00 94 4 \w -20.00 73.00 1.00 4.00 -- 40.20 -77.00 150.00 93 5 \w 31.00 102.00 1.00 10.00 -- 104.18-111.00 -30.00 71 6 \w 26.00 109.00 1.00 10.00 -- 104.18-111.00-180.00 83 7 \w 108.00 153.00 1.00 10.00 -- 104.18 77.00-180.00 45 8 \w 34.00 122.00 1.00 10.00 -- 104.18 -61.00-180.00 88 9 \w 20.00 106.00 1.00 10.00 -- 104.18 -94.00 30.00 86 10 \w 47.00 132.00 1.00 10.00 -- 104.18 -45.00 0.00 85 11 \w 76.00 168.00 1.00 10.00 -- 104.18 61.00 -30.00 92 ; _diffrn_measurement_device 'kappa diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0175825000 _diffrn_orient_matrix_UB_12 0.1887513000 _diffrn_orient_matrix_UB_13 0.0073933000 _diffrn_orient_matrix_UB_21 0.0733810000 _diffrn_orient_matrix_UB_22 -0.0449773000 _diffrn_orient_matrix_UB_23 0.0346077000 _diffrn_orient_matrix_UB_31 0.0122647000 _diffrn_orient_matrix_UB_32 -0.0011369000 _diffrn_orient_matrix_UB_33 -0.1398500000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0180 _diffrn_reflns_av_unetI/netI 0.0266 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.969 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 4868 _diffrn_reflns_point_group_measured_fraction_full 0.926 _diffrn_reflns_point_group_measured_fraction_max 0.887 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 72.565 _diffrn_reflns_theta_min 4.143 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_current 0.80 _diffrn_source_power 0.040 _diffrn_source_target Cu _diffrn_source_type 'SuperNova (Cu) X-ray Source' _diffrn_source_voltage 50 _exptl_absorpt_coefficient_mu 0.696 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.87004 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020) 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 1.291 _exptl_crystal_description block _exptl_crystal_F_000 704 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: diethyl ether' _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.234 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.034 _refine_ls_abs_structure_details ; Flack x determined using 1161 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.05(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 227 _refine_ls_number_reflns 3026 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.040 _refine_ls_R_factor_all 0.0295 _refine_ls_R_factor_gt 0.0283 _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^)+(0.0331P)^2^+0.5582P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0686 _refine_ls_wR_factor_ref 0.0695 _reflns_Friedel_coverage 0.700 _reflns_Friedel_fraction_full 0.846 _reflns_Friedel_fraction_max 0.791 _reflns_number_gt 2924 _reflns_number_total 3026 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1sc02439f2.cif _cod_data_source_block wguo5cult _cod_database_code 1564261 _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. ; _shelx_estimated_absorpt_t_max 0.979 _shelx_estimated_absorpt_t_min 0.966 _diffrn_oxdiff_digest_frames ; 01b48b6497bb50c5924c95c4e8d1f8f79b00027e33e ; _diffrn_oxdiff_digest_hkl ; 015a54516616a3b9c9604bd0f9139bb51b0d70 ; _reflns_odcompleteness_completeness 99.51 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C2(H2) 2.b Aromatic/amide H refined with riding coordinates: N1(H1), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C22(H22), C23(H23), C25(H25), C26(H26) 2.c Idealised Me refined as rotating group: C27(H27A,H27B,H27C) ; _shelx_res_file ; wguo5cult.res created by SHELXL-2014/7 TITL wguo5cult_a.res in C2 REM Old TITL REM SHELXT solution in C2 REM R1 0.079, Rweak 0.027, Alpha 0.001, Orientation as input REM Flack x = 0.081 ( 0.105 ) from Parsons' quotients REM Formula found by SHELXT: C21 N O3 CELL 1.54184 20.228 7.9448 10.7105 90 94.888 90 ZERR 4 0.0004 0.0002 0.0002 0 0.002 0 LATT -7 SYMM -X,+Y,-Z SFAC C H N O UNIT 84 76 4 12 L.S. 10 PLAN 20 SIZE 0.03 0.05 0.05 BOND $H list 4 CONF fmap 2 acta OMIT -18 6 5 OMIT -24 0 4 REM REM REM WGHT 0.033100 0.558200 FVAR 0.59642 O1 4 0.459080 0.234987 0.134115 11.00000 0.01611 0.04086 = 0.01651 -0.00509 0.00171 -0.00515 O2 4 0.462878 0.299417 0.339707 11.00000 0.01388 0.02569 = 0.01537 -0.00185 0.00315 -0.00266 O3 4 0.866874 0.218793 0.111149 11.00000 0.01273 0.03067 = 0.02097 -0.00280 0.00165 0.00090 N1 3 0.593370 0.250618 0.141281 11.00000 0.01438 0.02070 = 0.01625 -0.00507 0.00041 -0.00004 AFIX 43 H1 2 0.568826 0.205719 0.080718 11.00000 -1.20000 AFIX 0 C1 1 0.489209 0.280637 0.228620 11.00000 0.01574 0.01429 = 0.01689 0.00092 0.00303 0.00010 C2 1 0.562722 0.325902 0.243497 11.00000 0.01247 0.01724 = 0.01473 -0.00024 0.00238 0.00094 AFIX 13 H2 2 0.582005 0.273346 0.321002 11.00000 -1.20000 AFIX 0 C3 1 0.570585 0.516913 0.258591 11.00000 0.00876 0.01735 = 0.01878 -0.00039 0.00186 0.00060 C4 1 0.584413 0.617653 0.157821 11.00000 0.01516 0.02103 = 0.01655 -0.00092 0.00367 0.00041 AFIX 43 H4 2 0.587591 0.569609 0.079379 11.00000 -1.20000 AFIX 0 C5 1 0.593520 0.790453 0.174122 11.00000 0.01751 0.01919 = 0.02379 0.00493 0.00441 -0.00032 AFIX 43 H5 2 0.603001 0.857467 0.106726 11.00000 -1.20000 AFIX 0 C6 1 0.588434 0.862303 0.290828 11.00000 0.01931 0.01550 = 0.02754 -0.00108 0.00215 -0.00092 AFIX 43 H6 2 0.594553 0.977553 0.301736 11.00000 -1.20000 AFIX 0 C7 1 0.574210 0.762375 0.391491 11.00000 0.02224 0.02064 = 0.01996 -0.00294 0.00247 0.00039 AFIX 43 H7 2 0.570441 0.810938 0.469571 11.00000 -1.20000 AFIX 0 C8 1 0.565616 0.590250 0.375759 11.00000 0.01631 0.01987 = 0.01584 0.00178 0.00260 -0.00098 AFIX 43 H8 2 0.556513 0.523513 0.443543 11.00000 -1.20000 AFIX 0 C11 1 0.394267 0.271420 0.346201 11.00000 0.01505 0.01904 = 0.01664 -0.00508 0.00406 -0.00189 C12 1 0.346971 0.359432 0.272490 11.00000 0.01970 0.01986 = 0.02186 0.00210 0.00387 0.00011 AFIX 43 H12 2 0.359187 0.434046 0.211624 11.00000 -1.20000 AFIX 0 C13 1 0.280458 0.333958 0.291336 11.00000 0.01869 0.02739 = 0.02608 -0.00132 0.00191 0.00324 AFIX 43 H13 2 0.247726 0.391478 0.242189 11.00000 -1.20000 AFIX 0 C14 1 0.262679 0.223292 0.382982 11.00000 0.01572 0.02910 = 0.02862 -0.00805 0.00796 -0.00468 AFIX 43 H14 2 0.218169 0.207356 0.395432 11.00000 -1.20000 AFIX 0 C15 1 0.311282 0.136489 0.455980 11.00000 0.02628 0.02237 = 0.02309 -0.00181 0.00965 -0.00602 AFIX 43 H15 2 0.299385 0.062380 0.517441 11.00000 -1.20000 AFIX 0 C16 1 0.377694 0.160240 0.437294 11.00000 0.02294 0.01803 = 0.01563 -0.00108 0.00307 -0.00083 AFIX 43 H16 2 0.410557 0.101961 0.485555 11.00000 -1.20000 AFIX 0 C21 1 0.662146 0.248683 0.138019 11.00000 0.01638 0.01378 = 0.01708 0.00235 0.00201 0.00114 C22 1 0.689517 0.173967 0.034778 11.00000 0.01846 0.01776 = 0.01567 -0.00116 -0.00040 0.00015 AFIX 43 H22 2 0.661519 0.129020 -0.030162 11.00000 -1.20000 AFIX 0 C23 1 0.757261 0.166656 0.028824 11.00000 0.02045 0.02183 = 0.01560 -0.00076 0.00433 0.00283 AFIX 43 H23 2 0.774561 0.117149 -0.040025 11.00000 -1.20000 AFIX 0 C24 1 0.800057 0.233169 0.125589 11.00000 0.01343 0.01946 = 0.01914 0.00337 0.00207 0.00138 C25 1 0.774039 0.305453 0.228456 11.00000 0.01562 0.02102 = 0.01854 -0.00179 -0.00136 0.00057 AFIX 43 H25 2 0.802288 0.348919 0.293618 11.00000 -1.20000 AFIX 0 C26 1 0.705219 0.313073 0.234323 11.00000 0.01705 0.01978 = 0.01646 -0.00182 0.00312 0.00169 AFIX 43 H26 2 0.688096 0.361888 0.303611 11.00000 -1.20000 AFIX 0 C27 1 0.911241 0.291063 0.206551 11.00000 0.01381 0.03781 = 0.03327 -0.00862 -0.00012 0.00004 AFIX 137 H27A 2 0.956092 0.275620 0.185847 11.00000 -1.50000 H27B 2 0.905473 0.237189 0.285115 11.00000 -1.50000 H27C 2 0.902106 0.409162 0.213086 11.00000 -1.50000 AFIX 0 HKLF 4 REM wguo5cult_a.res in C2 REM R1 = 0.0283 for 2924 Fo > 4sig(Fo) and 0.0295 for all 3026 data REM 227 parameters refined using 1 restraints END WGHT 0.0331 0.5581 REM Highest difference peak 0.234, deepest hole -0.200, 1-sigma level 0.034 Q1 1 0.5692 0.2778 0.0627 11.00000 0.05 0.23 Q2 1 0.5261 0.3019 0.2403 11.00000 0.05 0.18 Q3 1 0.6772 0.2454 0.0748 11.00000 0.05 0.15 Q4 1 0.9576 0.2184 0.1976 11.00000 0.05 0.13 Q5 1 0.5378 0.3114 0.4667 11.00000 0.05 0.11 Q6 1 0.5477 0.3314 0.4858 11.00000 0.05 0.11 Q7 1 0.7378 0.3060 0.2267 11.00000 0.05 0.11 Q8 1 0.3888 0.2608 0.4129 11.00000 0.05 0.10 Q9 1 0.7239 0.1832 0.0362 11.00000 0.05 0.10 Q10 1 0.5833 0.4634 0.4812 11.00000 0.05 0.10 Q11 1 0.6373 0.1977 -0.0738 11.00000 0.05 0.10 Q12 1 0.6395 0.2667 -0.0740 11.00000 0.05 0.10 Q13 1 0.6882 0.2758 0.3796 11.00000 0.05 0.10 Q14 1 0.1918 0.1201 0.3024 11.00000 0.05 0.10 Q15 1 0.7773 0.2271 0.0739 11.00000 0.05 0.10 Q16 1 0.5995 0.3483 0.0018 11.00000 0.05 0.10 Q17 1 0.7795 0.1623 0.0991 11.00000 0.05 0.10 Q18 1 0.7847 0.2227 0.1917 11.00000 0.05 0.09 Q19 1 0.1509 0.1370 0.3748 11.00000 0.05 0.09 Q20 1 0.8399 0.0880 -0.0761 11.00000 0.05 0.09 ; _shelx_res_checksum 9347 _shelx_hkl_file ; 0 0 -1 368.61 3.31 0 0 1 368.75 3.44 0 0 -1 371.70 4.66 0 0 -2 6562.95 28.48 0 0 -2 6599.96 19.89 0 0 3 306.82 5.60 0 0 -3 301.65 7.97 0 0 4 377.49 7.42 0 0 -4 385.03 10.59 0 0 -5 2.04 2.77 0 0 5 4.04 1.59 0 0 -6 2.33 2.69 0 0 -7 245.66 11.89 0 0 -8 845.32 15.86 0 0 -8 863.59 14.37 0 0 -9 77.44 4.89 0 0 -9 76.57 5.95 0 0 -10 411.72 12.91 0 0 -10 403.45 10.86 0 0 -11 131.83 7.46 0 0 -11 126.48 5.87 0 0 -12 150.38 5.15 0 2 1 1202.09 11.88 0 -2 -1 1181.13 14.81 0 2 -1 1210.23 15.52 0 2 -2 9999.00 49.23 0 2 2 9942.73 28.96 0 -2 -2 9856.41 48.92 0 2 3 718.15 4.92 0 2 -3 740.92 14.62 0 -2 -3 743.92 15.43 0 2 -4 2861.68 30.68 0 -2 -4 2945.75 35.02 0 -2 -5 189.92 10.16 0 2 -5 180.55 8.16 0 -2 6 158.26 7.92 0 -2 -6 142.26 9.41 0 2 -6 148.55 7.67 0 -2 -7 137.23 9.82 0 2 -7 129.53 5.85 0 -2 -7 131.31 5.79 0 2 -7 131.57 5.75 0 -2 -8 351.85 8.87 0 -2 -8 356.55 10.65 0 2 -8 362.50 10.48 0 -2 -8 363.26 16.42 0 2 -8 360.64 11.05 0 2 -9 283.15 10.22 0 -2 -9 258.63 8.01 0 2 -9 263.69 10.26 0 -2 -9 266.57 10.06 0 -2 -10 122.58 7.23 0 2 -10 116.52 6.76 0 2 -11 324.80 10.08 0 -2 -11 336.25 10.59 0 2 -12 137.56 5.45 0 -2 -12 135.49 5.66 0 -4 0 2048.59 25.88 0 4 0 2040.98 27.20 0 4 1 742.19 14.93 0 -4 1 746.67 15.21 0 4 -1 744.45 17.71 0 -4 -1 736.67 16.56 0 4 -2 3361.33 39.71 0 4 2 3358.53 28.72 0 -4 -2 3354.61 38.21 0 4 -3 448.78 15.63 0 -4 -3 424.88 14.67 0 4 -4 1970.22 33.72 0 -4 -4 1926.84 33.20 0 -4 -5 18.96 4.17 0 4 -5 21.80 4.28 0 -4 -6 15.03 2.57 0 -4 6 8.62 3.01 0 4 -6 11.34 2.16 0 -4 -6 20.85 4.73 0 4 -6 14.34 3.64 0 -4 -6 13.00 2.39 0 4 -6 11.04 1.95 0 -4 -7 402.75 17.42 0 4 -7 370.82 9.46 0 -4 -7 401.39 11.01 0 -4 -7 391.03 10.11 0 4 -7 394.51 10.71 0 -4 7 401.66 14.82 0 -4 -8 462.94 12.33 0 4 -8 492.32 10.76 0 4 -8 493.04 12.77 0 4 -9 103.47 6.13 0 -4 -9 112.71 5.57 0 -4 -9 116.51 6.54 0 -4 -10 22.01 3.34 0 4 -10 24.65 3.19 0 4 -11 173.52 6.16 0 -4 -11 173.50 5.94 0 4 -12 89.21 3.21 0 -6 0 201.21 7.84 0 6 0 181.86 9.76 0 -6 -1 99.62 7.07 0 -6 -1 105.24 5.67 0 -6 1 121.00 6.28 0 6 -1 124.07 8.90 0 -6 2 99.36 5.97 0 6 -2 85.11 7.71 0 -6 -2 96.62 5.53 0 -6 -2 92.76 7.23 0 -6 3 296.41 10.27 0 6 -3 275.38 14.14 0 -6 -3 293.67 13.05 0 -6 -3 292.28 9.40 0 -6 -4 1755.53 20.89 0 -6 -4 1760.26 23.74 0 -6 4 1783.32 25.49 0 -6 -4 1785.92 32.64 0 -6 -5 346.75 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18 6 -2 94.37 4.13 18 -6 -2 96.39 4.31 18 -6 -2 96.84 4.25 18 -6 -1 4.58 1.44 18 -6 -1 3.11 1.47 18 6 -1 2.77 1.40 18 -6 0 8.93 1.39 18 -6 0 6.00 1.57 18 6 0 5.08 1.61 18 -6 1 44.85 2.95 18 6 1 49.02 2.98 18 -6 2 142.65 4.59 18 6 2 126.19 4.07 19 -1 -8 48.72 2.44 19 1 -8 48.28 2.65 19 -1 -8 40.48 2.56 19 1 -8 42.65 2.64 19 1 -7 59.63 3.85 19 1 -7 61.70 3.24 19 -1 -7 62.79 3.91 19 1 -6 56.78 4.43 19 -1 -6 54.26 4.24 19 1 -5 159.86 7.58 19 -1 -5 142.68 7.09 19 1 -4 66.46 5.32 19 -1 -4 57.64 4.83 19 1 -3 78.95 5.57 19 -1 -3 80.98 5.46 19 1 -2 177.77 7.79 19 -1 -2 172.96 6.70 19 -1 -2 170.86 7.40 19 1 -1 91.05 5.32 19 -1 -1 78.75 5.05 19 1 -1 97.96 5.15 19 -1 -1 89.88 5.26 19 1 0 271.30 8.12 19 1 0 264.01 8.90 19 -1 0 268.66 9.59 19 -1 0 270.16 8.06 19 1 1 202.29 8.41 19 -1 1 218.19 9.01 19 1 2 146.23 7.52 19 -1 2 145.72 7.59 19 1 3 13.28 3.04 19 -1 3 14.99 2.98 19 1 4 6.70 2.55 19 -1 4 13.50 2.77 19 1 5 21.12 2.97 19 -1 5 21.39 2.84 19 -1 6 32.23 2.73 19 1 6 22.99 2.54 19 1 7 7.35 1.31 19 -3 -7 12.57 1.80 19 3 -7 12.56 1.84 19 3 -7 12.72 1.59 19 3 -6 34.10 3.25 19 -3 -6 27.97 2.83 19 3 -5 51.68 4.31 19 -3 -5 49.41 3.92 19 3 -4 194.47 8.16 19 -3 -4 182.85 7.59 19 -3 -3 51.56 3.62 19 3 -3 52.46 4.35 19 -3 -3 51.37 4.29 19 -3 -2 106.08 5.51 19 3 -2 110.67 5.97 19 -3 -2 97.13 5.49 19 -3 -1 12.72 2.35 19 3 -1 14.18 2.52 19 -3 -1 19.78 3.01 19 3 -1 14.12 2.56 19 3 0 190.40 6.65 19 3 0 181.94 6.46 19 -3 0 190.55 8.08 19 3 0 185.70 6.95 19 -3 0 185.59 6.54 19 3 1 107.02 5.44 19 -3 1 108.86 6.28 19 3 1 111.71 5.10 19 3 2 59.25 4.38 19 -3 2 62.20 4.79 19 3 3 47.40 4.04 19 -3 3 50.71 4.19 19 3 4 67.78 4.52 19 -3 4 69.71 4.38 19 3 5 5.54 1.71 19 -3 5 4.04 1.27 -19 3 -6 89.07 3.07 19 3 6 106.20 4.19 19 -5 -6 7.90 1.23 19 5 -6 5.21 1.13 19 5 -5 44.25 2.86 19 -5 -5 52.19 3.02 19 -5 -4 24.79 2.47 19 -5 -3 6.92 1.83 19 -5 -3 5.64 1.44 19 5 -3 8.90 1.93 19 -5 -2 29.33 2.78 19 -5 -2 27.19 2.65 19 5 -2 29.23 2.81 19 -5 -1 67.81 4.10 19 5 -1 72.82 4.15 19 -5 -1 68.56 3.76 19 -5 0 33.51 3.07 19 5 0 40.67 3.16 19 -5 0 32.07 2.34 19 -5 1 65.67 4.05 19 5 1 64.10 3.51 19 5 2 63.75 2.98 19 5 2 63.72 3.14 19 -5 3 80.30 3.58 19 5 3 81.99 3.44 -19 5 -4 66.28 3.01 19 5 4 60.72 2.70 20 0 -8 75.68 2.92 20 0 -7 124.08 4.99 20 0 -6 178.98 6.92 20 0 -5 17.39 3.00 20 0 -4 14.54 2.87 20 0 -3 18.20 3.18 20 0 -2 9.92 2.43 20 0 -1 344.29 9.54 20 0 -1 341.55 9.56 20 0 0 9.59 1.90 20 0 0 6.90 2.13 20 0 1 0.14 1.94 20 0 2 0.34 2.00 20 0 3 126.15 6.73 20 0 4 0.69 1.68 20 0 5 0.95 1.60 20 0 6 29.99 2.40 20 -2 -7 19.95 2.06 20 2 -7 14.21 1.87 20 -2 -6 23.87 2.75 20 2 -6 26.57 2.92 20 2 -5 66.22 4.67 20 -2 -5 63.42 4.44 20 2 -4 25.90 3.40 20 -2 -4 34.68 3.71 20 2 -3 49.28 4.33 20 -2 -3 43.50 4.00 20 -2 -2 5.36 2.07 20 2 -2 6.57 2.25 20 -2 -2 4.51 1.63 20 2 -1 162.67 6.45 20 -2 -1 162.38 6.96 20 2 -1 165.47 6.37 20 -2 -1 158.01 6.38 20 2 0 98.99 4.56 20 2 0 95.45 5.01 20 2 0 95.92 4.56 20 -2 0 99.31 5.82 20 -2 0 94.24 4.50 20 2 1 1.21 1.61 20 -2 1 1.18 1.79 20 2 2 162.98 7.11 20 -2 2 163.32 7.52 20 2 3 102.08 5.71 20 -2 3 97.41 5.67 20 2 4 4.02 1.84 20 -2 4 3.07 1.73 20 2 5 8.96 1.84 20 -2 5 10.77 1.79 20 -2 6 100.47 3.14 20 2 6 113.67 4.06 20 4 -6 45.38 2.64 20 -4 -6 47.78 2.65 20 4 -5 48.43 3.25 20 -4 -5 49.94 3.25 20 4 -4 34.58 3.12 20 -4 -4 34.69 3.05 20 4 -3 103.71 5.14 20 -4 -3 90.86 3.98 20 -4 -3 96.12 4.77 20 4 -2 58.70 3.90 20 -4 -2 51.33 3.39 20 4 -2 60.45 4.01 20 -4 -2 52.41 3.54 20 4 -1 103.61 4.60 20 -4 -1 110.61 5.22 20 4 -1 109.07 5.00 20 -4 -1 107.03 4.62 20 -4 0 6.94 1.29 20 -4 0 9.51 2.12 20 4 0 8.44 1.90 20 4 1 41.12 2.60 20 -4 1 42.68 3.48 20 4 1 40.14 2.82 20 4 2 36.41 2.71 20 -4 2 40.81 3.35 20 4 3 58.92 3.33 20 -4 3 59.18 3.48 20 4 4 145.07 4.65 20 -4 4 155.20 4.51 21 -1 -7 11.95 1.62 21 1 -7 9.10 1.50 21 -1 -6 85.54 4.39 21 1 -6 89.35 4.48 21 -1 -5 5.15 1.97 21 1 -5 6.23 2.00 21 1 -4 68.49 4.70 21 -1 -4 68.40 4.69 21 1 -3 82.71 5.04 21 -1 -3 71.53 4.79 21 1 -2 53.37 4.11 21 -1 -2 56.87 3.42 21 -1 -2 53.86 4.02 21 -1 -1 12.91 2.20 21 1 -1 11.85 2.08 21 -1 -1 14.79 2.30 21 -1 0 73.75 4.80 21 1 0 66.03 4.14 21 -1 1 79.46 5.16 21 1 1 76.77 4.69 21 -1 2 133.22 6.51 21 1 2 135.54 6.34 21 -1 3 3.50 1.99 21 1 3 2.74 1.86 21 -1 4 127.96 5.59 21 1 4 128.09 5.56 21 -1 5 48.99 2.99 21 1 5 44.95 2.97 21 1 6 74.67 2.82 21 3 -6 29.54 2.26 21 -3 -6 34.62 2.41 21 -3 -5 17.20 2.17 21 3 -5 14.97 2.13 21 3 -4 51.37 3.59 21 -3 -4 49.04 3.50 21 3 -3 72.61 4.35 21 -3 -3 73.34 4.29 21 -3 -2 5.49 1.82 21 3 -2 5.14 1.74 21 -3 -2 2.37 1.28 21 -3 -1 8.41 1.68 21 3 -1 6.67 1.72 21 -3 -1 7.72 1.79 21 -3 0 19.02 2.56 21 3 0 17.11 2.01 21 -3 1 1.71 1.52 21 3 1 8.42 1.51 21 3 2 59.72 3.48 21 -3 2 62.53 4.06 21 3 3 4.20 1.42 21 -3 3 7.32 1.71 21 3 4 93.88 3.87 21 -3 4 94.73 3.82 21 3 5 24.19 1.76 21 -5 -3 60.30 2.61 21 -5 -1 86.81 3.33 21 -5 0 97.49 3.61 21 5 0 93.70 3.00 21 -5 1 20.15 1.74 22 0 -7 46.05 2.26 22 0 -6 53.50 3.09 22 0 -5 23.69 2.62 22 0 -4 6.33 2.09 22 0 -3 96.87 5.02 22 0 -2 4.02 1.56 22 0 -1 35.12 2.66 22 0 -1 41.81 3.06 22 0 0 30.94 2.93 22 0 1 98.73 5.07 22 0 2 10.50 2.08 22 0 3 92.46 4.67 22 0 4 45.42 3.01 22 0 5 6.61 1.19 22 -2 -6 36.32 2.34 22 2 -6 30.32 2.17 22 -2 -5 1.55 1.42 22 2 -5 0.90 1.29 22 -2 -4 6.52 1.83 22 2 -4 4.69 1.75 22 2 -3 75.09 4.08 22 -2 -3 72.54 4.08 22 -2 -2 -0.40 1.32 22 2 -2 -0.52 1.39 22 -2 -2 -1.17 1.02 22 2 -1 27.80 2.26 22 -2 -1 25.70 2.51 22 -2 -1 26.70 2.29 22 -2 0 109.35 5.05 22 -2 1 38.40 3.27 22 2 1 40.61 2.83 22 -2 2 123.97 5.38 22 2 2 121.31 4.81 22 -2 3 30.13 2.62 22 2 3 28.31 2.40 22 2 4 4.79 1.16 22 -2 4 5.44 1.24 22 -4 -4 14.72 1.47 22 4 -4 12.52 1.41 22 4 -3 26.52 1.97 22 -4 -3 35.97 2.20 22 -4 -2 65.10 2.53 22 -4 -2 70.35 2.82 22 -4 -1 14.28 1.59 22 -4 0 2.04 1.14 22 -4 1 38.96 2.47 22 -4 2 44.08 2.38 23 -1 -6 69.48 2.74 23 1 -6 77.35 2.84 23 -1 -5 39.99 2.55 23 1 -5 35.46 2.43 23 -1 -4 50.71 3.06 23 1 -4 51.59 3.13 23 -1 -3 43.10 2.93 23 1 -3 45.74 2.91 23 -1 -2 33.18 2.45 23 1 -2 34.12 2.52 23 -1 -1 6.91 1.22 23 -1 -1 6.22 1.21 23 -1 0 90.33 4.05 23 1 0 90.81 3.41 23 1 1 20.58 2.00 23 -1 1 19.50 2.21 23 -1 2 156.69 5.29 23 1 2 150.36 4.91 23 -1 3 27.59 2.18 23 1 3 33.01 2.32 23 -1 4 76.82 2.89 23 -3 -4 18.80 1.63 23 3 -4 14.98 1.47 23 -3 -3 6.29 1.17 23 3 -3 3.97 1.08 23 -3 -2 15.31 1.46 23 3 -2 9.30 1.16 23 -3 -1 9.22 1.17 23 -3 0 9.97 1.45 23 -3 1 43.25 2.53 23 -3 2 74.42 2.97 24 0 -4 122.08 3.93 24 0 -3 2.57 1.06 24 0 -2 3.21 0.94 24 0 1 89.55 3.10 24 0 2 -1.55 0.95 TITL wguo5CuLT in C2/m REM C2/m (#12 in standard setting) CELL 1.54184 20.227995 7.944834 10.710516 90.0000 94.8879 90.0000 ZERR 7.00 0.000378 0.000155 0.000201 0.0000 0.0017 0.0000 LATT 7 SYMM -x, y,-z SFAC C H N O UNIT 77.00 70.00 7.00 7.00 TREF HKLF 4 END _computing_structure_solution 'SHELXT 2014/4 (Sheldrick, 2014)' ; _shelx_hkl_checksum 57380 _olex2_date_sample_data_collection 2020-10-23 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.227 _oxdiff_exptl_absorpt_empirical_full_min 0.877 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.45908(7) 0.2350(2) 0.13411(12) 0.0245(3) Uani 1 1 d . . . . . O2 O 0.46288(6) 0.29942(19) 0.33971(12) 0.0182(3) Uani 1 1 d . . . . . O3 O 0.86687(6) 0.2188(2) 0.11115(12) 0.0214(3) Uani 1 1 d . . . . . N1 N 0.59337(7) 0.2506(2) 0.14128(14) 0.0172(3) Uani 1 1 d . . . . . H1 H 0.5688 0.2057 0.0807 0.021 Uiso 1 1 calc R . . . . C1 C 0.48921(9) 0.2806(2) 0.22862(17) 0.0155(4) Uani 1 1 d . . . . . C2 C 0.56272(9) 0.3259(2) 0.24350(17) 0.0147(4) Uani 1 1 d . . . . . H2 H 0.5820 0.2733 0.3210 0.018 Uiso 1 1 calc R . . . . C3 C 0.57058(9) 0.5169(3) 0.25859(17) 0.0149(4) Uani 1 1 d . . . . . C4 C 0.58441(9) 0.6177(3) 0.15782(18) 0.0174(4) Uani 1 1 d . . . . . H4 H 0.5876 0.5696 0.0794 0.021 Uiso 1 1 calc R . . . . C5 C 0.59352(9) 0.7905(3) 0.17412(18) 0.0200(4) Uani 1 1 d . . . . . H5 H 0.6030 0.8575 0.1067 0.024 Uiso 1 1 calc R . . . . C6 C 0.58843(9) 0.8623(3) 0.29083(19) 0.0208(4) Uani 1 1 d . . . . . H6 H 0.5946 0.9776 0.3017 0.025 Uiso 1 1 calc R . . . . C7 C 0.57421(10) 0.7624(3) 0.39149(18) 0.0209(4) Uani 1 1 d . . . . . H7 H 0.5704 0.8109 0.4696 0.025 Uiso 1 1 calc R . . . . C8 C 0.56562(10) 0.5903(3) 0.37576(18) 0.0173(4) Uani 1 1 d . . . . . H8 H 0.5565 0.5235 0.4435 0.021 Uiso 1 1 calc R . . . . C11 C 0.39427(9) 0.2714(3) 0.34620(17) 0.0168(4) Uani 1 1 d . . . . . C12 C 0.34697(10) 0.3594(3) 0.27249(19) 0.0204(4) Uani 1 1 d . . . . . H12 H 0.3592 0.4340 0.2116 0.024 Uiso 1 1 calc R . . . . C13 C 0.28046(10) 0.3340(3) 0.2913(2) 0.0241(5) Uani 1 1 d . . . . . H13 H 0.2477 0.3915 0.2422 0.029 Uiso 1 1 calc R . . . . C14 C 0.26268(10) 0.2233(3) 0.3830(2) 0.0241(5) Uani 1 1 d . . . . . H14 H 0.2182 0.2074 0.3954 0.029 Uiso 1 1 calc R . . . . C15 C 0.31128(10) 0.1365(3) 0.45598(19) 0.0235(5) Uani 1 1 d . . . . . H15 H 0.2994 0.0624 0.5174 0.028 Uiso 1 1 calc R . . . . C16 C 0.37769(10) 0.1602(3) 0.43729(17) 0.0188(4) Uani 1 1 d . . . . . H16 H 0.4106 0.1020 0.4856 0.023 Uiso 1 1 calc R . . . . C21 C 0.66215(9) 0.2487(3) 0.13802(17) 0.0157(4) Uani 1 1 d . . . . . C22 C 0.68952(9) 0.1740(3) 0.03478(17) 0.0174(4) Uani 1 1 d . . . . . H22 H 0.6615 0.1290 -0.0302 0.021 Uiso 1 1 calc R . . . . C23 C 0.75726(10) 0.1667(3) 0.02882(18) 0.0191(4) Uani 1 1 d . . . . . H23 H 0.7746 0.1171 -0.0400 0.023 Uiso 1 1 calc R . . . . C24 C 0.80006(9) 0.2332(3) 0.12559(18) 0.0173(4) Uani 1 1 d . . . . . C25 C 0.77404(9) 0.3055(3) 0.22846(18) 0.0186(4) Uani 1 1 d . . . . . H25 H 0.8023 0.3489 0.2936 0.022 Uiso 1 1 calc R . . . . C26 C 0.70522(9) 0.3131(3) 0.23432(18) 0.0177(4) Uani 1 1 d . . . . . H26 H 0.6881 0.3619 0.3036 0.021 Uiso 1 1 calc R . . . . C27 C 0.91124(10) 0.2911(3) 0.2066(2) 0.0284(5) Uani 1 1 d . . . . . H27A H 0.9561 0.2756 0.1858 0.043 Uiso 1 1 calc GR . . . . H27B H 0.9055 0.2372 0.2851 0.043 Uiso 1 1 calc GR . . . . H27C H 0.9021 0.4092 0.2131 0.043 Uiso 1 1 calc GR . . . . 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 0.0161(6) 0.0409(10) 0.0165(7) -0.0051(6) 0.0017(5) -0.0052(6) O2 0.0139(6) 0.0257(8) 0.0154(6) -0.0018(6) 0.0032(5) -0.0027(5) O3 0.0127(6) 0.0307(9) 0.0210(7) -0.0028(6) 0.0017(5) 0.0009(6) N1 0.0144(7) 0.0207(9) 0.0162(7) -0.0051(7) 0.0004(6) 0.0000(6) C1 0.0157(8) 0.0143(10) 0.0169(9) 0.0009(7) 0.0030(7) 0.0001(7) C2 0.0125(8) 0.0172(10) 0.0147(9) -0.0002(7) 0.0024(7) 0.0009(7) C3 0.0088(8) 0.0174(10) 0.0188(9) -0.0004(7) 0.0019(6) 0.0006(7) C4 0.0152(9) 0.0210(11) 0.0166(9) -0.0009(8) 0.0037(7) 0.0004(7) C5 0.0175(9) 0.0192(10) 0.0238(10) 0.0049(8) 0.0044(7) -0.0003(8) C6 0.0193(9) 0.0155(10) 0.0275(11) -0.0011(8) 0.0021(8) -0.0009(8) C7 0.0222(9) 0.0206(11) 0.0200(9) -0.0029(8) 0.0025(7) 0.0004(8) C8 0.0163(9) 0.0199(10) 0.0158(9) 0.0018(7) 0.0026(7) -0.0010(7) C11 0.0151(8) 0.0190(10) 0.0166(8) -0.0051(8) 0.0041(6) -0.0019(7) C12 0.0197(9) 0.0199(11) 0.0219(10) 0.0021(8) 0.0039(7) 0.0001(8) C13 0.0187(10) 0.0274(12) 0.0261(10) -0.0013(8) 0.0019(8) 0.0032(8) C14 0.0157(9) 0.0291(12) 0.0286(10) -0.0080(9) 0.0080(7) -0.0047(8) C15 0.0263(11) 0.0224(11) 0.0231(10) -0.0018(9) 0.0097(8) -0.0060(8) C16 0.0229(10) 0.0180(11) 0.0156(9) -0.0011(8) 0.0031(7) -0.0008(8) C21 0.0164(9) 0.0138(9) 0.0171(8) 0.0023(7) 0.0020(7) 0.0011(7) C22 0.0185(9) 0.0178(10) 0.0157(9) -0.0012(7) -0.0004(7) 0.0002(7) C23 0.0205(9) 0.0218(11) 0.0156(9) -0.0008(8) 0.0043(7) 0.0028(8) C24 0.0134(8) 0.0195(10) 0.0191(9) 0.0034(8) 0.0021(7) 0.0014(7) C25 0.0156(9) 0.0210(10) 0.0185(9) -0.0018(8) -0.0014(7) 0.0006(7) C26 0.0170(9) 0.0198(10) 0.0165(9) -0.0018(8) 0.0031(7) 0.0017(7) C27 0.0138(9) 0.0378(13) 0.0333(11) -0.0086(10) -0.0001(8) 0.0000(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' 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 C11 119.20(14) . . ? C24 O3 C27 116.79(15) . . ? C2 N1 H1 119.3 . . ? C21 N1 H1 119.3 . . ? C21 N1 C2 121.38(15) . . ? O1 C1 O2 124.68(17) . . ? O1 C1 C2 125.71(17) . . ? O2 C1 C2 109.61(15) . . ? N1 C2 C1 107.64(15) . . ? N1 C2 H2 107.6 . . ? N1 C2 C3 116.47(15) . . ? C1 C2 H2 107.6 . . ? C1 C2 C3 109.63(15) . . ? C3 C2 H2 107.6 . . ? C4 C3 C2 120.91(17) . . ? C4 C3 C8 119.49(18) . . ? C8 C3 C2 119.58(17) . . ? C3 C4 H4 119.9 . . ? C3 C4 C5 120.17(18) . . ? C5 C4 H4 119.9 . . ? C4 C5 H5 120.0 . . ? C6 C5 C4 119.96(19) . . ? C6 C5 H5 120.0 . . ? C5 C6 H6 120.0 . . ? C5 C6 C7 120.07(19) . . ? C7 C6 H6 120.0 . . ? C6 C7 H7 120.0 . . ? C8 C7 C6 120.10(19) . . ? C8 C7 H7 120.0 . . ? C3 C8 H8 119.9 . . ? C7 C8 C3 120.21(19) . . ? C7 C8 H8 119.9 . . ? C12 C11 O2 121.92(17) . . ? C12 C11 C16 122.13(17) . . ? C16 C11 O2 115.77(16) . . ? C11 C12 H12 120.8 . . ? C11 C12 C13 118.39(19) . . ? C13 C12 H12 120.8 . . ? C12 C13 H13 119.8 . . ? C14 C13 C12 120.43(19) . . ? C14 C13 H13 119.8 . . ? C13 C14 H14 120.0 . . ? C15 C14 C13 119.99(18) . . ? C15 C14 H14 120.0 . . ? C14 C15 H15 120.0 . . ? C14 C15 C16 119.97(19) . . ? C16 C15 H15 120.0 . . ? C11 C16 C15 119.07(18) . . ? C11 C16 H16 120.5 . . ? C15 C16 H16 120.5 . . ? N1 C21 C22 118.93(16) . . ? C26 C21 N1 122.75(16) . . ? C26 C21 C22 118.30(16) . . ? C21 C22 H22 119.6 . . ? C23 C22 C21 120.84(17) . . ? C23 C22 H22 119.6 . . ? C22 C23 H23 119.8 . . ? C22 C23 C24 120.37(17) . . ? C24 C23 H23 119.8 . . ? O3 C24 C23 115.93(17) . . ? O3 C24 C25 124.49(17) . . ? C25 C24 C23 119.58(17) . . ? C24 C25 H25 120.0 . . ? C24 C25 C26 120.01(18) . . ? C26 C25 H25 120.0 . . ? C21 C26 C25 120.90(17) . . ? C21 C26 H26 119.5 . . ? C25 C26 H26 119.5 . . ? O3 C27 H27A 109.5 . . ? O3 C27 H27B 109.5 . . ? O3 C27 H27C 109.5 . . ? H27A C27 H27B 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.193(2) . ? O2 C1 1.353(2) . ? O2 C11 1.413(2) . ? O3 C24 1.378(2) . ? O3 C27 1.422(2) . ? N1 H1 0.8600 . ? N1 C2 1.434(2) . ? N1 C21 1.395(2) . ? C1 C2 1.525(2) . ? C2 H2 0.9800 . ? C2 C3 1.533(3) . ? C3 C4 1.391(3) . ? C3 C8 1.395(3) . ? C4 H4 0.9300 . ? C4 C5 1.394(3) . ? C5 H5 0.9300 . ? C5 C6 1.386(3) . ? C6 H6 0.9300 . ? C6 C7 1.389(3) . ? C7 H7 0.9300 . ? C7 C8 1.387(3) . ? C8 H8 0.9300 . ? C11 C12 1.378(3) . ? C11 C16 1.378(3) . ? C12 H12 0.9300 . ? C12 C13 1.392(3) . ? C13 H13 0.9300 . ? C13 C14 1.388(3) . ? C14 H14 0.9300 . ? C14 C15 1.387(3) . ? C15 H15 0.9300 . ? C15 C16 1.388(3) . ? C16 H16 0.9300 . ? C21 C22 1.409(3) . ? C21 C26 1.390(3) . ? C22 H22 0.9300 . ? C22 C23 1.378(3) . ? C23 H23 0.9300 . ? C23 C24 1.396(3) . ? C24 C25 1.385(3) . ? C25 H25 0.9300 . ? C25 C26 1.400(3) . ? C26 H26 0.9300 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 N1 -19.7(3) . . . . ? O1 C1 C2 C3 107.9(2) . . . . ? O2 C1 C2 N1 160.11(15) . . . . ? O2 C1 C2 C3 -72.31(19) . . . . ? O2 C11 C12 C13 -175.07(18) . . . . ? O2 C11 C16 C15 174.94(17) . . . . ? O3 C24 C25 C26 -179.66(19) . . . . ? N1 C2 C3 C4 22.4(2) . . . . ? N1 C2 C3 C8 -155.78(16) . . . . ? N1 C21 C22 C23 -178.84(18) . . . . ? N1 C21 C26 C25 178.66(19) . . . . ? C1 O2 C11 C12 -57.3(2) . . . . ? C1 O2 C11 C16 127.40(18) . . . . ? C1 C2 C3 C4 -100.03(19) . . . . ? C1 C2 C3 C8 81.7(2) . . . . ? C2 N1 C21 C22 -179.56(17) . . . . ? C2 N1 C21 C26 2.4(3) . . . . ? C2 C3 C4 C5 -177.94(17) . . . . ? C2 C3 C8 C7 178.44(18) . . . . ? C3 C4 C5 C6 -0.4(3) . . . . ? C4 C3 C8 C7 0.2(3) . . . . ? C4 C5 C6 C7 -0.1(3) . . . . ? C5 C6 C7 C8 0.5(3) . . . . ? C6 C7 C8 C3 -0.6(3) . . . . ? C8 C3 C4 C5 0.3(3) . . . . ? C11 O2 C1 O1 -3.1(3) . . . . ? C11 O2 C1 C2 177.15(16) . . . . ? C11 C12 C13 C14 0.5(3) . . . . ? C12 C11 C16 C15 -0.3(3) . . . . ? C12 C13 C14 C15 -0.4(3) . . . . ? C13 C14 C15 C16 0.0(3) . . . . ? C14 C15 C16 C11 0.4(3) . . . . ? C16 C11 C12 C13 -0.1(3) . . . . ? C21 N1 C2 C1 -170.69(17) . . . . ? C21 N1 C2 C3 65.8(2) . . . . ? C21 C22 C23 C24 0.1(3) . . . . ? C22 C21 C26 C25 0.6(3) . . . . ? C22 C23 C24 O3 179.64(18) . . . . ? C22 C23 C24 C25 0.6(3) . . . . ? C23 C24 C25 C26 -0.7(3) . . . . ? C24 C25 C26 C21 0.1(3) . . . . ? C26 C21 C22 C23 -0.7(3) . . . . ? C27 O3 C24 C23 177.84(19) . . . . ? C27 O3 C24 C25 -3.1(3) . . . . ?