#------------------------------------------------------------------------------ #$Date: 2020-05-01 01:18:06 +0300 (Fri, 01 May 2020) $ #$Revision: 251334 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/79/1557968.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_1557968 loop_ _publ_author_name 'Fairley, Michael' 'Bole, Leonie' 'Mulks, Florian' 'Main, Laura' 'Kennedy, Alan' 'O'Hara, Charles T.' 'Garc\'ia-\'Alvarez, Joaqu\'in' 'Hevia, Eva' _publ_section_title ; Ultrafast Amidation of Esters using Lithium Amides under Aerobic Ambient Temperature Conditions in Sustainable Solvents ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D0SC01349H _journal_year 2020 _chemical_formula_moiety 'C30 H36 Li2 N6 O2' _chemical_formula_sum 'C30 H36 Li2 N6 O2' _chemical_formula_weight 526.53 _chemical_properties_physical Air-sensitive,Moisture-sensitive,Oxygen-sensitive _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2019-06-13 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-12-20 deposited with the CCDC. 2020-04-30 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 107.012(5) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.7406(4) _cell_length_b 10.9189(4) _cell_length_c 14.1465(7) _cell_measurement_reflns_used 2891 _cell_measurement_temperature 123.35(10) _cell_measurement_theta_max 72.3240 _cell_measurement_theta_min 6.2670 _cell_volume 1438.74(11) _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_environment N~2~ _diffrn_ambient_temperature 123.35(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0268 _diffrn_detector_type Sapphire3 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -4.00 42.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -99.0000 -150.0000 46 #__ type_ start__ end____ width___ exp.time_ 2 omega -21.00 69.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 57.0000 0.0000 90 #__ type_ start__ end____ width___ exp.time_ 3 omega 35.00 125.00 1.0000 1.4500 omega____ theta____ kappa____ phi______ frames - 56.0000 57.0000 0.0000 90 #__ type_ start__ end____ width___ exp.time_ 4 omega -13.00 77.00 1.0000 1.4500 omega____ theta____ kappa____ phi______ frames - 56.0000 -57.0000 120.0000 90 #__ type_ start__ end____ width___ exp.time_ 5 omega 18.00 60.00 1.0000 1.4500 omega____ theta____ kappa____ phi______ frames - 56.0000 -57.0000 0.0000 42 #__ type_ start__ end____ width___ exp.time_ 6 omega 39.00 125.00 1.0000 1.4500 omega____ theta____ kappa____ phi______ frames - 56.0000 57.0000 -120.0000 86 #__ type_ start__ end____ width___ exp.time_ 7 omega 35.00 117.00 1.0000 1.4500 omega____ theta____ kappa____ phi______ frames - 56.0000 57.0000 120.0000 82 #__ type_ start__ end____ width___ exp.time_ 8 omega 52.00 113.00 1.0000 1.4500 omega____ theta____ kappa____ phi______ frames - 56.0000 -125.0000 -60.0000 61 #__ type_ start__ end____ width___ exp.time_ 9 omega 18.00 75.00 1.0000 1.4500 omega____ theta____ kappa____ phi______ frames - 56.0000 -57.0000 -120.0000 57 #__ type_ start__ end____ width___ exp.time_ 10 omega 94.00 174.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 112.0000 77.0000 30.0000 80 #__ type_ start__ end____ width___ exp.time_ 11 omega 56.00 104.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 112.0000 -111.0000 90.0000 48 #__ type_ start__ end____ width___ exp.time_ 12 omega 45.00 70.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 112.0000 -111.0000 -30.0000 25 #__ type_ start__ end____ width___ exp.time_ 13 omega 53.00 93.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 112.0000 -25.0000 -60.0000 40 #__ type_ start__ end____ width___ exp.time_ 14 omega 84.00 115.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 112.0000 -111.0000 150.0000 31 #__ type_ start__ end____ width___ exp.time_ 15 omega 48.00 74.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 112.0000 -111.0000 150.0000 26 #__ type_ start__ end____ width___ exp.time_ 16 omega 103.00 133.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 112.0000 63.0000 -90.0000 30 #__ type_ start__ end____ width___ exp.time_ 17 omega 48.00 93.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 112.0000 -25.0000 0.0000 45 #__ type_ start__ end____ width___ exp.time_ 18 omega 42.00 107.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 112.0000 -111.0000 -90.0000 65 #__ type_ start__ end____ width___ exp.time_ 19 omega 50.00 135.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 112.0000 -77.0000 -60.0000 85 #__ type_ start__ end____ width___ exp.time_ 20 omega 52.00 78.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 112.0000 -63.0000 -120.0000 26 #__ type_ start__ end____ width___ exp.time_ 21 omega 100.00 133.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 112.0000 -63.0000 -120.0000 33 #__ type_ start__ end____ width___ exp.time_ 22 omega 110.00 176.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 112.0000 0.0000 -180.0000 66 #__ type_ start__ end____ width___ exp.time_ 23 omega 45.00 88.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 112.0000 0.0000 -180.0000 43 #__ type_ start__ end____ width___ exp.time_ 24 omega 40.00 73.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 112.0000 -25.0000 150.0000 33 #__ type_ start__ end____ width___ exp.time_ 25 omega 47.00 133.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 112.0000 -63.0000 60.0000 86 #__ type_ start__ end____ width___ exp.time_ 26 omega 143.00 168.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 112.0000 63.0000 -30.0000 25 #__ type_ start__ end____ width___ exp.time_ 27 omega 74.00 114.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 112.0000 -111.0000 -30.0000 40 #__ type_ start__ end____ width___ exp.time_ 28 omega 102.00 164.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 112.0000 77.0000 90.0000 62 #__ type_ start__ end____ width___ exp.time_ 29 omega 56.00 90.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 112.0000 -37.0000 90.0000 34 #__ type_ start__ end____ width___ exp.time_ 30 omega 91.00 127.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 112.0000 63.0000 -30.0000 36 #__ type_ start__ end____ width___ exp.time_ 31 omega 137.00 175.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 112.0000 63.0000 -90.0000 38 #__ type_ start__ end____ width___ exp.time_ 32 omega 93.00 147.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 112.0000 179.0000 -60.0000 54 #__ type_ start__ end____ width___ exp.time_ 33 omega 61.00 87.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 112.0000 179.0000 -60.0000 26 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.1404477000 _diffrn_orient_matrix_UB_12 -0.0737911000 _diffrn_orient_matrix_UB_13 -0.0365622000 _diffrn_orient_matrix_UB_21 0.0051492000 _diffrn_orient_matrix_UB_22 -0.0274790000 _diffrn_orient_matrix_UB_23 0.1078037000 _diffrn_orient_matrix_UB_31 -0.0871845000 _diffrn_orient_matrix_UB_32 0.1170943000 _diffrn_orient_matrix_UB_33 0.0021907000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0786 _diffrn_reflns_av_unetI/netI 0.0570 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 10712 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.198 _diffrn_reflns_theta_min 4.914 _diffrn_source 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.609 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.27783 _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 1.215 _exptl_crystal_description block _exptl_crystal_F_000 560 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _refine_diff_density_max 0.293 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.056 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 226 _refine_ls_number_reflns 2857 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.0720 _refine_ls_R_factor_gt 0.0591 _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^)+(0.1022P)^2^+0.1093P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1634 _refine_ls_wR_factor_ref 0.1830 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2274 _reflns_number_total 2857 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sc01349h2.cif _cod_data_source_block mf-3a _cod_database_code 1557968 _shelx_shelxl_version_number 2017/1 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _reflns_odcompleteness_completeness 99.73 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 71.98 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances O1-C12 = O1-C15 = O2-C20 = O2-C17 1.43 with sigma of 0.01 3. Uiso/Uaniso restraints and constraints Uanis(C18) = Uanis(C14) Uanis(O1) = Uanis(O2) 4. Others Sof(O2)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)= Sof(C17)=Sof(H17)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C19)=Sof(H19A)=Sof(H19B)=1- FVAR(1) Sof(O1)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C15)= Sof(H15)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C14)=Sof(H14A)=Sof(H14B)= FVAR(1) 5.a Ternary CH refined with riding coordinates: C17(H17), C15(H15) 5.b Secondary CH2 refined with riding coordinates: C18(H18A,H18B), C20(H20A,H20B), C19(H19A,H19B), C13(H13A,H13B), C12(H12A, H12B), C14(H14A,H14B) 5.c Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2), C3(H3), C4(H4), C8(H8), C7(H7), C9(H9), C10(H10) 5.d Idealised Me refined as rotating group: C21(H21A,H21B,H21C), C16(H16A,H16B,H16C) ; _shelx_res_file ; TITL mf-3a.res created by SHELXL-2017/1 at 10:16:44 on 13-Jun-2019 CELL 1.54184 9.7406 10.9189 14.1465 90 107.012 90 ZERR 2 0.0004 0.0004 0.0007 0 0.005 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC Li O N C H UNIT 4 4 12 60 72 DFIX 1.43 0.01 O1 C12 O1 C15 O2 C20 O2 C17 EADP C18 C14 EADP O1 O2 L.S. 12 PLAN 20 TEMP -150 BOND $H CONF fmap 2 ACTA MERG 2 OMIT 1 0 3 REM REM REM WGHT 0.102200 0.109300 FVAR 7.82753 0.47367 LI1 1 0.053227 0.388875 0.553656 11.00000 0.03495 0.02865 = 0.03526 0.00039 0.01403 0.00132 N1 3 0.148991 0.294553 0.461735 11.00000 0.03862 0.03225 = 0.03564 -0.00192 0.01753 -0.00693 N2 3 0.144250 0.502162 0.449759 11.00000 0.03192 0.02879 = 0.03754 0.00106 0.01819 0.00181 N3 3 0.130582 0.709993 0.446598 11.00000 0.03273 0.03155 = 0.03967 -0.00504 0.01454 0.00260 C1 4 0.175251 0.183457 0.431437 11.00000 0.05107 0.03008 = 0.03836 -0.00273 0.01598 -0.00925 AFIX 43 H1 5 0.147890 0.114426 0.462617 11.00000 -1.20000 AFIX 0 C2 4 0.239164 0.162106 0.358222 11.00000 0.04842 0.03200 = 0.03829 -0.00588 0.01270 -0.00091 AFIX 43 H2 5 0.256292 0.081208 0.339680 11.00000 -1.20000 AFIX 0 C3 4 0.277772 0.263951 0.312346 11.00000 0.03635 0.04081 = 0.03314 -0.00071 0.01486 0.00536 AFIX 43 H3 5 0.321679 0.253446 0.261122 11.00000 -1.20000 AFIX 0 C4 4 0.252054 0.379787 0.341527 11.00000 0.03314 0.03533 = 0.03320 0.00672 0.01584 0.00614 AFIX 43 H4 5 0.278214 0.449642 0.310658 11.00000 -1.20000 AFIX 0 C5 4 0.186437 0.394179 0.417754 11.00000 0.02612 0.03040 = 0.03010 0.00159 0.01051 0.00005 C8 4 0.415436 0.740778 0.451041 11.00000 0.03186 0.03970 = 0.03760 0.00407 0.01220 -0.00213 AFIX 43 H8 5 0.512976 0.751162 0.452776 11.00000 -1.20000 AFIX 0 C6 4 0.212715 0.609873 0.445014 11.00000 0.03129 0.03000 = 0.02862 0.00092 0.01265 0.00252 C7 4 0.356865 0.624978 0.445473 11.00000 0.03062 0.03392 = 0.03719 0.00687 0.01414 0.00378 AFIX 43 H7 5 0.413608 0.555328 0.441944 11.00000 -1.20000 AFIX 0 C9 4 0.330261 0.842308 0.454095 11.00000 0.04383 0.03200 = 0.04160 -0.00369 0.01354 -0.00525 AFIX 43 H9 5 0.367560 0.923139 0.457843 11.00000 -1.20000 AFIX 0 C10 4 0.189947 0.820932 0.451470 11.00000 0.04210 0.03024 = 0.04509 -0.00816 0.01410 0.00241 AFIX 43 H10 5 0.131263 0.889877 0.453246 11.00000 -1.20000 AFIX 0 PART 2 O2 2 0.201395 0.428248 0.680009 -21.00000 0.03160 0.03560 = 0.03555 -0.00306 0.01316 -0.00213 C18 4 0.317701 0.571584 0.800186 -21.00000 0.04151 0.04628 = 0.05437 -0.01266 0.00904 -0.00059 AFIX 23 H18A 5 0.355331 0.521821 0.860761 -21.00000 -1.20000 H18B 5 0.314827 0.658754 0.818765 -21.00000 -1.20000 AFIX 0 C21 4 0.080084 0.478307 0.799388 -21.00000 0.04299 0.07766 = 0.04396 0.00259 0.02463 0.00656 AFIX 137 H21A 5 -0.010689 0.447609 0.755303 -21.00000 -1.50000 H21B 5 0.060443 0.543987 0.840838 -21.00000 -1.50000 H21C 5 0.130887 0.411457 0.841525 -21.00000 -1.50000 AFIX 0 C17 4 0.171046 0.526936 0.739107 -21.00000 0.03805 0.04326 = 0.03496 -0.00502 0.01570 0.00357 AFIX 13 H17 5 0.119044 0.594243 0.695079 -21.00000 -1.20000 AFIX 0 C20 4 0.350580 0.431033 0.683413 -21.00000 0.03244 0.05597 = 0.04823 -0.01571 0.01194 0.00347 AFIX 23 H20A 5 0.360959 0.423714 0.616086 -21.00000 -1.20000 H20B 5 0.403643 0.363051 0.724492 -21.00000 -1.20000 AFIX 0 C19 4 0.406768 0.553672 0.728721 -21.00000 0.03625 0.05544 = 0.04360 -0.00798 0.01435 -0.01217 AFIX 23 H19A 5 0.388533 0.619297 0.678275 -21.00000 -1.20000 H19B 5 0.510744 0.550159 0.763926 -21.00000 -1.20000 AFIX 0 PART 0 PART 1 O1 2 0.162858 0.427652 0.693062 21.00000 0.03160 0.03560 = 0.03555 -0.00306 0.01316 -0.00213 C13 4 0.122982 0.553096 0.817878 21.00000 0.04340 0.04620 = 0.03749 -0.00594 0.01704 0.00117 AFIX 23 H13A 5 0.124394 0.550182 0.888103 21.00000 -1.20000 H13B 5 0.051599 0.614500 0.782469 21.00000 -1.20000 AFIX 0 C12 4 0.092739 0.428314 0.769719 21.00000 0.04592 0.04536 = 0.03338 -0.00358 0.01823 -0.01188 AFIX 23 H12A 5 0.131797 0.362806 0.818571 21.00000 -1.20000 H12B 5 -0.011887 0.415503 0.741284 21.00000 -1.20000 AFIX 0 C15 4 0.260623 0.530971 0.707264 21.00000 0.03107 0.04524 = 0.03804 0.00090 0.01622 -0.00741 AFIX 13 H15 5 0.217569 0.595142 0.656876 21.00000 -1.20000 AFIX 0 C16 4 0.398131 0.488168 0.692194 21.00000 0.03174 0.11319 = 0.04848 -0.01237 0.01805 -0.00150 AFIX 137 H16A 5 0.441483 0.425700 0.741664 21.00000 -1.50000 H16B 5 0.464140 0.557580 0.699181 21.00000 -1.50000 H16C 5 0.379113 0.453102 0.625835 21.00000 -1.50000 AFIX 0 C14 4 0.271267 0.580056 0.807664 21.00000 0.04151 0.04628 = 0.05437 -0.01266 0.00904 -0.00059 AFIX 23 H14A 5 0.291366 0.669088 0.811526 21.00000 -1.20000 H14B 5 0.347066 0.537420 0.859317 21.00000 -1.20000 AFIX 0 HKLF 4 REM REM R1 = 0.0591 for 2274 Fo > 4sig(Fo) and 0.0720 for all 2857 data REM 226 parameters refined using 4 restraints END WGHT 0.1023 0.1094 REM Highest difference peak 0.293, deepest hole -0.259, 1-sigma level 0.056 Q1 1 0.2720 0.6177 0.4099 11.00000 0.05 0.29 Q2 1 0.2247 0.3859 0.3714 11.00000 0.05 0.28 Q3 1 0.2491 0.8291 0.4032 11.00000 0.05 0.28 Q4 1 0.3044 0.6287 0.4899 11.00000 0.05 0.26 Q5 1 0.1103 0.2978 0.5192 11.00000 0.05 0.25 Q6 1 0.2818 0.8315 0.5067 11.00000 0.05 0.24 Q7 1 0.1238 0.5002 0.5004 11.00000 0.05 0.22 Q8 1 0.1322 0.7639 0.4100 11.00000 0.05 0.21 Q9 1 0.0937 0.7034 0.4897 11.00000 0.05 0.21 Q10 1 0.4009 0.6837 0.4909 11.00000 0.05 0.20 Q11 1 0.1984 0.4121 0.2867 11.00000 0.05 0.20 Q12 1 0.1182 0.6828 0.4085 11.00000 0.05 0.20 Q13 1 0.1176 0.3995 0.6450 11.00000 0.05 0.18 Q14 1 0.0350 0.7008 0.4693 11.00000 0.05 0.18 Q15 1 0.0681 0.6979 0.4057 11.00000 0.05 0.18 Q16 1 0.2169 0.1769 0.4029 11.00000 0.05 0.17 Q17 1 0.3943 0.8896 0.4904 11.00000 0.05 0.17 Q18 1 0.0527 0.3405 0.4249 11.00000 0.05 0.17 Q19 1 0.1109 0.5384 0.4068 11.00000 0.05 0.17 Q20 1 0.1059 0.2648 0.4031 11.00000 0.05 0.16 ; _shelx_res_checksum 13692 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Li1 Li 0.0532(3) 0.3889(2) 0.5537(2) 0.0321(6) Uani 1 1 d . . . . . N1 N 0.14899(15) 0.29455(13) 0.46173(11) 0.0341(4) Uani 1 1 d . . . . . N2 N 0.14425(15) 0.50216(11) 0.44976(11) 0.0310(4) Uani 1 1 d . . . . . N3 N 0.13058(15) 0.70999(13) 0.44660(11) 0.0338(4) Uani 1 1 d . . . . . C1 C 0.1753(2) 0.18346(15) 0.43144(14) 0.0392(4) Uani 1 1 d . . . . . H1 H 0.147890 0.114426 0.462617 0.047 Uiso 1 1 calc R . . . . C2 C 0.2392(2) 0.16211(15) 0.35822(14) 0.0396(4) Uani 1 1 d . . . . . H2 H 0.256292 0.081208 0.339680 0.047 Uiso 1 1 calc R . . . . C3 C 0.27777(19) 0.26395(15) 0.31235(13) 0.0358(4) Uani 1 1 d . . . . . H3 H 0.321679 0.253446 0.261122 0.043 Uiso 1 1 calc R . . . . C4 C 0.25205(17) 0.37979(14) 0.34153(13) 0.0326(4) Uani 1 1 d . . . . . H4 H 0.278214 0.449642 0.310658 0.039 Uiso 1 1 calc R . . . . C5 C 0.18644(16) 0.39418(13) 0.41775(12) 0.0284(4) Uani 1 1 d . . . . . C8 C 0.41544(18) 0.74078(15) 0.45104(13) 0.0360(4) Uani 1 1 d . . . . . H8 H 0.512976 0.751162 0.452776 0.043 Uiso 1 1 calc R . . . . C6 C 0.21272(17) 0.60987(13) 0.44501(12) 0.0291(4) Uani 1 1 d . . . . . C7 C 0.35686(17) 0.62498(14) 0.44547(13) 0.0330(4) Uani 1 1 d . . . . . H7 H 0.413608 0.555328 0.441944 0.040 Uiso 1 1 calc R . . . . C9 C 0.3303(2) 0.84231(15) 0.45410(13) 0.0389(4) Uani 1 1 d . . . . . H9 H 0.367560 0.923139 0.457843 0.047 Uiso 1 1 calc R . . . . C10 C 0.18995(19) 0.82093(15) 0.45147(14) 0.0389(4) Uani 1 1 d . . . . . H10 H 0.131263 0.889877 0.453246 0.047 Uiso 1 1 calc R . . . . O2 O 0.2014(5) 0.4282(5) 0.6800(5) 0.0335(8) Uani 0.526(4) 1 d D . P A 2 C18 C 0.3177(7) 0.5716(9) 0.8002(8) 0.0485(13) Uani 0.526(4) 1 d . . P A 2 H18A H 0.355331 0.521821 0.860761 0.058 Uiso 0.526(4) 1 calc R . P A 2 H18B H 0.314827 0.658754 0.818765 0.058 Uiso 0.526(4) 1 calc R . P A 2 C21 C 0.0801(5) 0.4783(5) 0.7994(4) 0.0523(12) Uani 0.526(4) 1 d . . P A 2 H21A H -0.010689 0.447609 0.755303 0.078 Uiso 0.526(4) 1 calc GR . P A 2 H21B H 0.060443 0.543987 0.840838 0.078 Uiso 0.526(4) 1 calc GR . P A 2 H21C H 0.130887 0.411457 0.841525 0.078 Uiso 0.526(4) 1 calc GR . P A 2 C17 C 0.1710(4) 0.5269(3) 0.7391(3) 0.0377(8) Uani 0.526(4) 1 d D . P A 2 H17 H 0.119044 0.594243 0.695079 0.045 Uiso 0.526(4) 1 calc R . P A 2 C20 C 0.3506(5) 0.4310(4) 0.6834(4) 0.0455(10) Uani 0.526(4) 1 d D . P A 2 H20A H 0.360959 0.423714 0.616086 0.055 Uiso 0.526(4) 1 calc R . P A 2 H20B H 0.403643 0.363051 0.724492 0.055 Uiso 0.526(4) 1 calc R . P A 2 C19 C 0.4068(4) 0.5537(4) 0.7287(3) 0.0445(9) Uani 0.526(4) 1 d . . P A 2 H19A H 0.388533 0.619297 0.678275 0.053 Uiso 0.526(4) 1 calc R . P A 2 H19B H 0.510744 0.550159 0.763926 0.053 Uiso 0.526(4) 1 calc R . P A 2 O1 O 0.1629(7) 0.4277(6) 0.6931(5) 0.0335(8) Uani 0.474(4) 1 d D . P A 1 C13 C 0.1230(5) 0.5531(4) 0.8179(3) 0.0413(9) Uani 0.474(4) 1 d . . P A 1 H13A H 0.124394 0.550182 0.888103 0.050 Uiso 0.474(4) 1 calc R . P A 1 H13B H 0.051599 0.614500 0.782469 0.050 Uiso 0.474(4) 1 calc R . P A 1 C12 C 0.0927(5) 0.4283(4) 0.7697(3) 0.0401(10) Uani 0.474(4) 1 d D . P A 1 H12A H 0.131797 0.362806 0.818571 0.048 Uiso 0.474(4) 1 calc R . P A 1 H12B H -0.011887 0.415503 0.741284 0.048 Uiso 0.474(4) 1 calc R . P A 1 C15 C 0.2606(4) 0.5310(3) 0.7073(3) 0.0368(9) Uani 0.474(4) 1 d D . P A 1 H15 H 0.217569 0.595142 0.656876 0.044 Uiso 0.474(4) 1 calc R . P A 1 C16 C 0.3981(6) 0.4882(7) 0.6922(5) 0.0631(17) Uani 0.474(4) 1 d . . P A 1 H16A H 0.441483 0.425700 0.741664 0.095 Uiso 0.474(4) 1 calc GR . P A 1 H16B H 0.464140 0.557580 0.699181 0.095 Uiso 0.474(4) 1 calc GR . P A 1 H16C H 0.379113 0.453102 0.625835 0.095 Uiso 0.474(4) 1 calc GR . P A 1 C14 C 0.2713(8) 0.5801(10) 0.8077(9) 0.0485(13) Uani 0.474(4) 1 d . . P A 1 H14A H 0.291366 0.669088 0.811526 0.058 Uiso 0.474(4) 1 calc R . P A 1 H14B H 0.347066 0.537420 0.859317 0.058 Uiso 0.474(4) 1 calc R . P A 1 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 Li1 0.0349(14) 0.0286(12) 0.0353(15) 0.0004(10) 0.0140(12) 0.0013(9) N1 0.0386(7) 0.0322(7) 0.0356(8) -0.0019(6) 0.0175(6) -0.0069(5) N2 0.0319(7) 0.0288(7) 0.0375(8) 0.0011(5) 0.0182(6) 0.0018(5) N3 0.0327(7) 0.0315(7) 0.0397(8) -0.0050(6) 0.0145(6) 0.0026(5) C1 0.0511(10) 0.0301(8) 0.0384(9) -0.0027(7) 0.0160(8) -0.0093(7) C2 0.0484(10) 0.0320(8) 0.0383(9) -0.0059(7) 0.0127(8) -0.0009(7) C3 0.0364(8) 0.0408(9) 0.0331(9) -0.0007(7) 0.0149(7) 0.0054(6) C4 0.0331(8) 0.0353(8) 0.0332(9) 0.0067(6) 0.0158(7) 0.0061(6) C5 0.0261(7) 0.0304(7) 0.0301(8) 0.0016(6) 0.0105(6) 0.0000(5) C8 0.0319(8) 0.0397(9) 0.0376(9) 0.0041(7) 0.0122(7) -0.0021(6) C6 0.0313(8) 0.0300(8) 0.0286(8) 0.0009(6) 0.0126(6) 0.0025(5) C7 0.0306(8) 0.0339(8) 0.0372(9) 0.0069(6) 0.0141(7) 0.0038(6) C9 0.0438(9) 0.0320(8) 0.0416(10) -0.0037(7) 0.0135(8) -0.0053(6) C10 0.0421(9) 0.0302(8) 0.0451(10) -0.0082(7) 0.0141(8) 0.0024(6) O2 0.032(3) 0.0356(7) 0.0355(18) -0.0031(9) 0.0132(14) -0.0021(15) C18 0.042(4) 0.0463(17) 0.054(2) -0.0127(14) 0.009(3) -0.001(3) C21 0.043(2) 0.078(4) 0.044(3) 0.003(3) 0.025(2) 0.007(3) C17 0.0380(18) 0.0433(17) 0.0350(17) -0.0050(14) 0.0157(14) 0.0036(13) C20 0.032(2) 0.056(2) 0.048(2) -0.0157(19) 0.0119(19) 0.0035(16) C19 0.0362(19) 0.055(2) 0.044(2) -0.0080(18) 0.0143(16) -0.0122(16) O1 0.032(3) 0.0356(7) 0.0355(18) -0.0031(9) 0.0132(14) -0.0021(15) C13 0.043(2) 0.046(2) 0.037(2) -0.0059(18) 0.0170(17) 0.0012(17) C12 0.046(2) 0.045(2) 0.033(2) -0.0036(18) 0.0182(19) -0.0119(19) C15 0.0311(18) 0.0452(19) 0.038(2) 0.0009(15) 0.0162(15) -0.0074(14) C16 0.032(3) 0.113(6) 0.048(3) -0.012(4) 0.018(2) -0.002(3) C14 0.042(4) 0.0463(17) 0.054(2) -0.0127(14) 0.009(3) -0.001(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Li Li 0.0008 0.0003 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' 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 N1 Li1 Li1 104.18(16) . 3_566 ? N1 Li1 N2 62.46(9) . . ? N1 Li1 N2 141.70(15) . 3_566 ? N1 Li1 N3 106.48(13) . 3_566 ? N1 Li1 C5 30.95(6) . . ? N1 Li1 C6 129.62(13) . 3_566 ? N2 Li1 Li1 49.88(9) . 3_566 ? N2 Li1 Li1 51.06(9) 3_566 3_566 ? N2 Li1 N2 100.94(11) 3_566 . ? N2 Li1 C5 125.26(13) 3_566 . ? N2 Li1 C5 31.51(6) . . ? N2 Li1 C6 31.66(6) 3_566 3_566 ? N2 Li1 C6 125.21(12) . 3_566 ? N3 Li1 Li1 104.91(15) 3_566 3_566 ? N3 Li1 N2 140.42(15) 3_566 . ? N3 Li1 N2 63.03(9) 3_566 3_566 ? N3 Li1 C5 128.25(13) 3_566 . ? N3 Li1 C6 31.41(6) 3_566 3_566 ? C5 Li1 Li1 76.95(12) . 3_566 ? C6 Li1 Li1 78.11(12) 3_566 3_566 ? C6 Li1 C5 135.71(13) 3_566 . ? O2 Li1 N1 109.18(17) . . ? O2 Li1 N2 98.32(18) . . ? O2 Li1 C5 105.68(16) . . ? O2 Li1 C6 117.11(17) . 3_566 ? O1 Li1 Li1 110.3(2) . 3_566 ? O1 Li1 N1 121.0(2) . . ? O1 Li1 N2 96.7(2) . 3_566 ? O1 Li1 N2 108.93(19) . . ? O1 Li1 N3 108.79(19) . 3_566 ? O1 Li1 C5 119.00(17) . . ? O1 Li1 C6 103.80(17) . 3_566 ? C1 N1 Li1 144.36(14) . . ? C1 N1 C5 118.63(15) . . ? C5 N1 Li1 96.87(13) . . ? Li1 N2 Li1 79.06(11) 3_566 . ? C5 N2 Li1 141.81(13) . 3_566 ? C5 N2 Li1 87.54(11) . . ? C6 N2 Li1 141.70(13) . . ? C6 N2 Li1 88.29(11) . 3_566 ? C6 N2 C5 121.90(14) . . ? C6 N3 Li1 95.32(13) . 3_566 ? C10 N3 Li1 145.74(14) . 3_566 ? C10 N3 C6 118.85(15) . . ? N1 C1 H1 117.7 . . ? N1 C1 C2 124.53(16) . . ? C2 C1 H1 117.7 . . ? C1 C2 H2 121.3 . . ? C1 C2 C3 117.30(15) . . ? C3 C2 H2 121.3 . . ? C2 C3 H3 120.1 . . ? C4 C3 C2 119.75(16) . . ? C4 C3 H3 120.1 . . ? C3 C4 H4 120.2 . . ? C3 C4 C5 119.57(15) . . ? C5 C4 H4 120.2 . . ? N1 C5 Li1 52.18(10) . . ? N1 C5 N2 113.11(14) . . ? N1 C5 C4 120.22(14) . . ? N2 C5 Li1 60.95(10) . . ? N2 C5 C4 126.48(14) . . ? C4 C5 Li1 171.94(13) . . ? C7 C8 H8 120.3 . . ? C7 C8 C9 119.41(15) . . ? C9 C8 H8 120.3 . . ? N2 C6 Li1 60.04(10) . 3_566 ? N2 C6 C7 126.92(14) . . ? N3 C6 Li1 53.28(10) . 3_566 ? N3 C6 N2 113.23(14) . . ? N3 C6 C7 119.70(14) . . ? C7 C6 Li1 172.96(13) . 3_566 ? C8 C7 C6 120.09(14) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C8 C9 H9 121.3 . . ? C10 C9 C8 117.39(15) . . ? C10 C9 H9 121.3 . . ? N3 C10 C9 124.53(15) . . ? N3 C10 H10 117.7 . . ? C9 C10 H10 117.7 . . ? C17 O2 Li1 117.6(4) . . ? C20 O2 Li1 119.6(4) . . ? C20 O2 C17 109.9(4) . . ? H18A C18 H18B 109.3 . . ? C17 C18 H18A 111.4 . . ? C17 C18 H18B 111.4 . . ? C17 C18 C19 101.8(6) . . ? C19 C18 H18A 111.4 . . ? C19 C18 H18B 111.4 . . ? H21A C21 H21B 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C17 C21 H21A 109.5 . . ? C17 C21 H21B 109.5 . . ? C17 C21 H21C 109.5 . . ? O2 C17 C18 104.5(4) . . ? O2 C17 C21 108.7(4) . . ? O2 C17 H17 109.8 . . ? C18 C17 H17 109.8 . . ? C21 C17 C18 113.9(5) . . ? C21 C17 H17 109.8 . . ? O2 C20 H20A 110.6 . . ? O2 C20 H20B 110.6 . . ? O2 C20 C19 105.6(4) . . ? H20A C20 H20B 108.8 . . ? C19 C20 H20A 110.6 . . ? C19 C20 H20B 110.6 . . ? C18 C19 H19A 111.6 . . ? C18 C19 H19B 111.6 . . ? C20 C19 C18 100.9(5) . . ? C20 C19 H19A 111.6 . . ? C20 C19 H19B 111.6 . . ? H19A C19 H19B 109.4 . . ? C12 O1 Li1 120.7(4) . . ? C12 O1 C15 109.2(5) . . ? C15 O1 Li1 116.2(4) . . ? H13A C13 H13B 109.3 . . ? C12 C13 H13A 111.5 . . ? C12 C13 H13B 111.5 . . ? C12 C13 C14 101.3(5) . . ? C14 C13 H13A 111.5 . . ? C14 C13 H13B 111.5 . . ? O1 C12 C13 105.7(4) . . ? O1 C12 H12A 110.6 . . ? O1 C12 H12B 110.6 . . ? C13 C12 H12A 110.6 . . ? C13 C12 H12B 110.6 . . ? H12A C12 H12B 108.7 . . ? O1 C15 H15 108.9 . . ? O1 C15 C16 108.5(4) . . ? O1 C15 C14 105.7(5) . . ? C16 C15 H15 108.9 . . ? C16 C15 C14 115.7(4) . . ? C14 C15 H15 108.9 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 C14 H14A 111.3 . . ? C13 C14 H14B 111.3 . . ? C15 C14 C13 102.5(6) . . ? C15 C14 H14A 111.3 . . ? C15 C14 H14B 111.3 . . ? H14A C14 H14B 109.2 . . ? 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 Li1 Li1 2.889(5) 3_566 ? Li1 N1 2.081(3) . ? Li1 N2 2.289(3) . ? Li1 N2 2.250(3) 3_566 ? Li1 N3 2.090(3) 3_566 ? Li1 C5 2.616(3) . ? Li1 C6 2.596(3) 3_566 ? Li1 O2 1.988(7) . ? Li1 O1 1.994(8) . ? N1 C1 1.336(2) . ? N1 C5 1.355(2) . ? N2 C5 1.3685(19) . ? N2 C6 1.363(2) . ? N3 C6 1.3587(19) . ? N3 C10 1.335(2) . ? C1 H1 0.9500 . ? C1 C2 1.375(3) . ? C2 H2 0.9500 . ? C2 C3 1.394(2) . ? C3 H3 0.9500 . ? C3 C4 1.376(2) . ? C4 H4 0.9500 . ? C4 C5 1.414(2) . ? C8 H8 0.9500 . ? C8 C7 1.380(2) . ? C8 C9 1.393(2) . ? C6 C7 1.412(2) . ? C7 H7 0.9500 . ? C9 H9 0.9500 . ? C9 C10 1.376(2) . ? C10 H10 0.9500 . ? O2 C17 1.446(5) . ? O2 C20 1.440(5) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C18 C17 1.517(9) . ? C18 C19 1.525(8) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C21 C17 1.495(6) . ? C17 H17 1.0000 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C20 C19 1.516(6) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? O1 C12 1.441(6) . ? O1 C15 1.452(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C13 C12 1.513(6) . ? C13 C14 1.522(8) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C15 H15 1.0000 . ? C15 C16 1.492(6) . ? C15 C14 1.493(12) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? 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 Li1 N1 C1 C2 174.7(2) . . . . ? Li1 N1 C5 N2 -1.40(17) . . . . ? Li1 N1 C5 C4 -176.76(15) . . . . ? Li1 N2 C5 Li1 -68.8(2) 3_566 . . . ? Li1 N2 C5 N1 1.26(16) . . . . ? Li1 N2 C5 N1 -67.5(3) 3_566 . . . ? Li1 N2 C5 C4 107.5(2) 3_566 . . . ? Li1 N2 C5 C4 176.28(16) . . . . ? Li1 N2 C6 Li1 -69.9(2) . . . 3_566 ? Li1 N2 C6 N3 3.24(16) 3_566 . . . ? Li1 N2 C6 N3 -66.6(3) . . . . ? Li1 N2 C6 C7 108.9(2) . . . . ? Li1 N2 C6 C7 178.75(18) 3_566 . . . ? Li1 N3 C6 N2 -3.50(18) 3_566 . . . ? Li1 N3 C6 C7 -179.37(16) 3_566 . . . ? Li1 N3 C10 C9 176.2(2) 3_566 . . . ? Li1 O2 C17 C18 -155.4(5) . . . . ? Li1 O2 C17 C21 82.6(5) . . . . ? Li1 O2 C20 C19 128.0(4) . . . . ? Li1 O1 C12 C13 -125.1(4) . . . . ? Li1 O1 C15 C16 -83.0(5) . . . . ? Li1 O1 C15 C14 152.4(4) . . . . ? N1 C1 C2 C3 -0.5(3) . . . . ? N2 C6 C7 C8 -172.96(17) . . . . ? N3 C6 C7 C8 2.3(3) . . . . ? C1 N1 C5 Li1 176.7(2) . . . . ? C1 N1 C5 N2 175.28(14) . . . . ? C1 N1 C5 C4 -0.1(2) . . . . ? C1 C2 C3 C4 0.4(3) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C3 C4 C5 N1 -0.1(2) . . . . ? C3 C4 C5 N2 -174.75(16) . . . . ? C5 N1 C1 C2 0.4(3) . . . . ? C5 N2 C6 Li1 155.18(18) . . . 3_566 ? C5 N2 C6 N3 158.42(15) . . . . ? C5 N2 C6 C7 -26.1(3) . . . . ? C8 C9 C10 N3 0.3(3) . . . . ? C6 N2 C5 Li1 153.96(18) . . . . ? C6 N2 C5 N1 155.22(15) . . . . ? C6 N2 C5 C4 -29.8(3) . . . . ? C6 N3 C10 C9 0.7(3) . . . . ? C7 C8 C9 C10 0.1(3) . . . . ? C9 C8 C7 C6 -1.3(3) . . . . ? C10 N3 C6 Li1 177.4(2) . . . 3_566 ? C10 N3 C6 N2 173.94(15) . . . . ? C10 N3 C6 C7 -1.9(3) . . . . ? O2 C20 C19 C18 33.4(6) . . . . ? C17 O2 C20 C19 -12.6(6) . . . . ? C17 C18 C19 C20 -40.9(6) . . . . ? C20 O2 C17 C18 -13.9(7) . . . . ? C20 O2 C17 C21 -135.9(5) . . . . ? C19 C18 C17 O2 34.4(7) . . . . ? C19 C18 C17 C21 152.9(5) . . . . ? O1 C15 C14 C13 -31.8(8) . . . . ? C12 O1 C15 C16 136.4(5) . . . . ? C12 O1 C15 C14 11.7(7) . . . . ? C12 C13 C14 C15 38.9(7) . . . . ? C15 O1 C12 C13 13.5(7) . . . . ? C16 C15 C14 C13 -151.9(5) . . . . ? C14 C13 C12 O1 -32.5(7) . . . . ?