#------------------------------------------------------------------------------ #$Date: 2020-05-16 06:54:24 +0300 (Sat, 16 May 2020) $ #$Revision: 252083 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157502.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_7157502 loop_ _publ_author_name 'Yang, Junxian' 'He, Zeyuan' 'Hong, Liang' 'Sun, Wangsheng' 'Wang, Rui' _publ_section_title ; Asymmetric N-Aminoalkylation of 3-Substituted Indoles by N- protected N,O-acetals: An Access to Chiral Propargyl Aminals ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D0OB00795A _journal_year 2020 _chemical_absolute_configuration ad _chemical_formula_moiety 'C26 H24 N2 O2 S' _chemical_formula_sum 'C26 H24 N2 O2 S' _chemical_formula_weight 428.53 _space_group_crystal_system tetragonal _space_group_IT_number 96 _space_group_name_Hall 'P 4nw 2abw' _space_group_name_H-M_alt 'P 43 21 2' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2019-02-25 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-03-27 deposited with the CCDC. 2020-05-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 9.3559(2) _cell_length_b 9.3559(2) _cell_length_c 60.611(3) _cell_measurement_reflns_used 8250 _cell_measurement_temperature 292.01(10) _cell_measurement_theta_max 64.6380 _cell_measurement_theta_min 4.7640 _cell_volume 5305.5(3) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _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 292.01(10) _diffrn_detector_area_resol_mean 16.0733 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.975 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -87.00 -52.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 178.0000 -30.0000 35 #__ type_ start__ end____ width___ exp.time_ 2 omega -76.00 -38.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 -63.0000 -150.0000 38 #__ type_ start__ end____ width___ exp.time_ 3 omega -84.00 -58.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 178.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 4 omega -19.00 16.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 -63.0000 -150.0000 35 #__ type_ start__ end____ width___ exp.time_ 5 omega 77.00 122.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 154.0000 -145.0000 45 #__ type_ start__ end____ width___ exp.time_ 6 omega 52.00 122.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 57.0000 -30.0000 70 #__ type_ start__ end____ width___ exp.time_ 7 omega 49.00 79.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 57.0000 -180.0000 30 #__ type_ start__ end____ width___ exp.time_ 8 omega 20.00 46.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 81.0000 -71.8715 26 #__ type_ start__ end____ width___ exp.time_ 9 omega 21.00 47.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 79.0000 -28.0199 26 #__ type_ start__ end____ width___ exp.time_ 10 omega 85.00 178.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 50.0000 120.0000 93 #__ type_ start__ end____ width___ exp.time_ 11 omega 34.00 92.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -25.0000 -150.0000 58 #__ type_ start__ end____ width___ exp.time_ 12 omega 82.00 108.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 69.0000 -105.0520 26 #__ type_ start__ end____ width___ exp.time_ 13 omega 87.00 128.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 -150.0000 41 #__ type_ start__ end____ width___ exp.time_ 14 omega 131.00 178.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 -150.0000 47 #__ type_ start__ end____ width___ exp.time_ 15 omega 37.00 92.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -38.0000 90.0000 55 #__ type_ start__ end____ width___ exp.time_ 16 omega 38.00 148.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 0.0000 90.0000 110 #__ type_ start__ end____ width___ exp.time_ 17 omega 53.00 128.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -63.0000 -150.0000 75 #__ type_ start__ end____ width___ exp.time_ 18 omega 35.00 60.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -25.0000 60.0000 25 #__ type_ start__ end____ width___ exp.time_ 19 omega 130.00 168.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 111.0000 120.0000 38 #__ type_ start__ end____ width___ exp.time_ 20 omega -79.00 14.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 -51.0000 40.0000 93 #__ type_ start__ end____ width___ exp.time_ 21 omega -79.00 23.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -8.5000 -77.0000 -90.0000 102 #__ type_ start__ end____ width___ exp.time_ 22 omega 31.00 125.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 51.0000 -172.0000 94 #__ type_ start__ end____ width___ exp.time_ 23 omega 32.00 123.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 57.0000 90.0000 91 #__ type_ start__ end____ width___ exp.time_ 24 omega -17.00 86.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 54.0000 -77.0000 -150.0000 103 #__ type_ start__ end____ width___ exp.time_ 25 omega 84.00 175.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 63.0000 -180.0000 91 #__ type_ start__ end____ width___ exp.time_ 26 omega 35.00 115.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -111.0000 -120.0000 80 #__ type_ start__ end____ width___ exp.time_ 27 omega 76.00 157.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 30.0000 81 #__ type_ start__ end____ width___ exp.time_ 28 omega 68.00 178.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 25.0000 -30.0000 110 #__ type_ start__ end____ width___ exp.time_ 29 omega 100.00 178.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 111.0000 -120.0000 78 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0233486000 _diffrn_orient_matrix_UB_12 0.0410345000 _diffrn_orient_matrix_UB_13 -0.0243483000 _diffrn_orient_matrix_UB_21 -0.1282919000 _diffrn_orient_matrix_UB_22 -0.0937255000 _diffrn_orient_matrix_UB_23 -0.0066887000 _diffrn_orient_matrix_UB_31 -0.1005353000 _diffrn_orient_matrix_UB_32 0.1290276000 _diffrn_orient_matrix_UB_33 0.0028905000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_unetI/netI 0.0301 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.975 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 73 _diffrn_reflns_limit_l_min -73 _diffrn_reflns_number 39201 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.973 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 70.919 _diffrn_reflns_theta_min 4.783 _diffrn_source 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.248 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.21466 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.073 _exptl_crystal_description block _exptl_crystal_F_000 1808 _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.438 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.054 _refine_ls_abs_structure_details ; Flack x determined using 1294 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.079(16) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.868 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 301 _refine_ls_number_reflns 4996 _refine_ls_number_restraints 66 _refine_ls_restrained_S_all 0.891 _refine_ls_R_factor_all 0.0950 _refine_ls_R_factor_gt 0.0870 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1797P)^2^+3.8300P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2483 _refine_ls_wR_factor_ref 0.2589 _reflns_Friedel_coverage 0.633 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.969 _reflns_number_gt 4236 _reflns_number_total 4996 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00795a2.cif _cod_data_source_block yangjx_0109 _cod_original_cell_volume 5305.5(4) _cod_database_code 7157502 _shelx_shelxl_version_number 2018/3 _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 99.83 _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 C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2. Uiso/Uaniso restraints and constraints Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C14) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 Uanis(C20) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C19') \\sim Ueq, Uanis(S1) \\sim Ueq, Uanis(S1') \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 3. Others Fixed Sof: H20(0.5) H20A(0.3) H21(0.7) H21A(0.5) S1(0.5) C19(0.7) H19(0.7) S1'(0.5) C19'(0.3) H19'(0.3) 4.a Ternary CH refined with riding coordinates: C15(H15) 4.b Aromatic/amide H refined with riding coordinates: N2(H2), C0AA(H0AA), C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C20(H20), C20(H20A), C21(H21), C21(H21A), C19(H19), C19'(H19') 4.c Idealised Me refined as rotating group: C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C) ; _shelx_res_file ; TITL yangjx_0109 in P41212 #92 yangjx_0109.res created by SHELXL-2018/3 at 15:38:45 on 25-Feb-2019 REM reset to P41212 #92 CELL 1.54184 9.355931 9.355931 60.610775 90 90 90 ZERR 8 0.000246 0.000246 0.003008 0 0 0 LATT -1 SYMM 0.5-Y,0.5+X,0.75+Z SYMM -X,-Y,0.5+Z SYMM 0.5+Y,0.5-X,0.25+Z SYMM 0.5+X,0.5-Y,0.25-Z SYMM 0.5-X,0.5+Y,0.75-Z SYMM +Y,+X,-Z SYMM -Y,-X,0.5-Z SFAC C H N O S UNIT 208 192 16 16 8 ISOR 0.01 0.02 C10 C11 C13 C12 C14 ISOR 0.01 0.02 C20 C21 C19 C19' S1 S1' L.S. 10 PLAN 20 BOND ABIN fmap 2 acta OMIT 1 1 10 OMIT 1 1 12 OMIT 0 0 16 OMIT 0 1 7 OMIT 0 2 20 OMIT 0 2 4 OMIT 1 1 8 OMIT 1 1 0 OMIT 1 1 16 OMIT 0 1 18 OMIT 0 0 20 OMIT 0 2 13 OMIT 6 6 6 REM REM REM WGHT 0.179700 3.830000 FVAR 3.13856 O1 4 0.840922 0.280812 0.643255 11.00000 0.04058 0.06660 = 0.08645 -0.01154 -0.00640 0.00799 O2 4 0.618512 0.364050 0.651270 11.00000 0.04794 0.06173 = 0.07405 -0.00839 0.00193 0.00856 N1 3 0.738853 0.254368 0.582300 11.00000 0.05457 0.05350 = 0.06319 -0.00467 -0.00078 -0.00023 N2 3 0.654116 0.255673 0.619609 11.00000 0.03872 0.06062 = 0.06638 -0.00118 0.00084 0.00350 AFIX 43 H2 2 0.565131 0.273096 0.617281 11.00000 -1.20000 AFIX 0 C0AA 1 0.669345 0.216489 0.562831 11.00000 0.06900 0.06529 = 0.07247 -0.00790 -0.00556 0.00356 AFIX 43 H0AA 2 0.604572 0.141621 0.561451 11.00000 -1.20000 AFIX 0 C2 1 0.709878 0.304824 0.546124 11.00000 0.08264 0.06095 = 0.06994 -0.00224 0.00370 0.02036 C3 1 0.814158 0.404390 0.555469 11.00000 0.08163 0.05687 = 0.07207 -0.00087 0.01892 0.01104 C4 1 0.893264 0.517471 0.547511 11.00000 0.13077 0.06651 = 0.09317 0.00667 0.04067 -0.00827 AFIX 43 H4 2 0.885004 0.545546 0.532848 11.00000 -1.20000 AFIX 0 C5 1 0.983974 0.587775 0.561450 11.00000 0.12625 0.06655 = 0.11110 -0.00096 0.03971 -0.03111 AFIX 43 H5 2 1.040171 0.661272 0.555840 11.00000 -1.20000 AFIX 0 C6 1 0.995229 0.554277 0.583268 11.00000 0.09943 0.05817 = 0.11348 -0.00981 0.02034 -0.02475 AFIX 43 H6 2 1.056831 0.606313 0.592240 11.00000 -1.20000 AFIX 0 C7 1 0.915242 0.442659 0.592287 11.00000 0.06992 0.05693 = 0.08187 -0.00449 0.00724 -0.00981 AFIX 43 H7 2 0.920798 0.419476 0.607183 11.00000 -1.20000 AFIX 0 C8 1 0.827914 0.368752 0.578073 11.00000 0.06053 0.04808 = 0.06949 -0.00243 0.00756 0.00050 C9 1 0.659761 0.295408 0.523090 11.00000 0.14109 0.08838 = 0.07585 -0.00969 -0.00003 0.01466 C10 1 0.752342 0.332093 0.505601 11.00000 0.23082 0.18564 = 0.13918 -0.00013 0.01439 -0.01275 AFIX 43 H10 2 0.845867 0.361979 0.507996 11.00000 -1.20000 AFIX 0 C11 1 0.687202 0.319143 0.481934 11.00000 0.21932 0.20173 = 0.14457 0.01014 0.01298 -0.01408 AFIX 43 H11 2 0.739691 0.339716 0.469297 11.00000 -1.20000 AFIX 0 C12 1 0.554182 0.277508 0.481110 11.00000 0.19370 0.18701 = 0.16052 0.02444 -0.02198 0.00908 AFIX 43 H12 2 0.502426 0.303782 0.468654 11.00000 -1.20000 AFIX 0 C13 1 0.488860 0.205567 0.495419 11.00000 0.20616 0.20194 = 0.16311 -0.03258 -0.01648 -0.00940 AFIX 43 H13 2 0.411650 0.147567 0.491782 11.00000 -1.20000 AFIX 0 C14 1 0.539702 0.217671 0.517647 11.00000 0.18237 0.18780 = 0.10429 -0.02871 -0.02258 -0.02468 AFIX 43 H14 2 0.489788 0.171311 0.528821 11.00000 -1.20000 AFIX 0 C15 1 0.735457 0.179276 0.603267 11.00000 0.03950 0.04628 = 0.07414 -0.00089 0.00153 -0.00286 AFIX 13 H15 2 0.833930 0.171111 0.608633 11.00000 -1.20000 AFIX 0 C16 1 0.678169 0.033553 0.600493 11.00000 0.04667 0.04681 = 0.08820 0.00131 0.00237 -0.00066 C17 1 0.630780 -0.084863 0.599187 11.00000 0.05714 0.05033 = 0.08863 0.00301 -0.00649 0.00195 C18 1 0.571410 -0.223261 0.596873 11.00000 0.05788 0.04045 = 0.10719 0.00588 -0.00554 0.00375 C20 1 0.495836 -0.442535 0.582666 11.00000 0.10679 0.06580 = 0.16027 -0.02758 -0.00969 -0.00579 PART 1 AFIX 43 H20 2 0.486046 -0.523784 0.573956 10.50000 -1.20000 AFIX 43 PART 0 PART 2 H20A 2 0.479044 -0.505713 0.571107 10.30000 -1.20000 AFIX 0 PART 0 C21 1 0.429129 -0.430878 0.600998 11.00000 0.10138 0.07618 = 0.14492 0.02591 -0.01406 -0.03227 PART 1 AFIX 43 H21 2 0.350509 -0.483963 0.605582 10.70000 -1.20000 AFIX 43 PART 0 PART 2 H21A 2 0.371407 -0.505173 0.605950 10.50000 -1.20000 AFIX 0 PART 0 C22 1 0.716003 0.300662 0.638669 11.00000 0.04457 0.04563 = 0.07430 0.00322 0.00593 0.00535 C23 1 0.659417 0.421748 0.673454 11.00000 0.06237 0.06921 = 0.08110 -0.01858 0.00021 -0.00942 C24 1 0.768105 0.535826 0.671007 11.00000 0.07615 0.10226 = 0.15282 -0.04906 0.02565 -0.03519 AFIX 137 H24A 2 0.856195 0.494799 0.665921 11.00000 -1.50000 H24B 2 0.783384 0.581352 0.685004 11.00000 -1.50000 H24C 2 0.735160 0.605243 0.660510 11.00000 -1.50000 AFIX 0 C25 1 0.518159 0.485258 0.681099 11.00000 0.07117 0.10619 = 0.10419 -0.04814 0.01195 -0.01059 AFIX 137 H25A 2 0.489815 0.559972 0.671163 11.00000 -1.50000 H25B 2 0.529240 0.523840 0.695675 11.00000 -1.50000 H25C 2 0.446284 0.412038 0.681281 11.00000 -1.50000 AFIX 0 C26 1 0.705085 0.302813 0.687829 11.00000 0.09628 0.11672 = 0.07776 -0.00907 -0.01586 0.00948 AFIX 137 H26A 2 0.633520 0.229285 0.687698 11.00000 -1.50000 H26B 2 0.717580 0.337270 0.702623 11.00000 -1.50000 H26C 2 0.793847 0.264550 0.682514 11.00000 -1.50000 AFIX 0 PART 1 S1 5 0.594202 -0.316317 0.575339 10.50000 0.13409 0.07850 = 0.14123 -0.02376 0.02314 -0.00417 C19 1 0.504615 -0.312005 0.613895 10.70000 0.07164 0.06874 = 0.08741 0.01294 0.00344 -0.02548 AFIX 43 H19 2 0.507393 -0.299109 0.629104 10.70000 -1.20000 AFIX 0 PART 0 PART 2 S1' 5 0.445095 -0.287531 0.615506 10.50000 0.09037 0.07100 = 0.09660 0.00879 0.01045 -0.01970 C19' 1 0.609779 -0.326767 0.584545 10.30000 0.07311 0.06592 = 0.09008 0.00417 0.00931 -0.00091 AFIX 43 H19' 2 0.697837 -0.331162 0.577459 10.30000 -1.20000 AFIX 0 HKLF 4 REM yangjx_0109 in P41212 #92 REM wR2 = 0.2589, GooF = S = 0.868, Restrained GooF = 0.891 for all data REM R1 = 0.0870 for 4236 Fo > 4sig(Fo) and 0.0950 for all 4996 data REM 301 parameters refined using 66 restraints END WGHT 0.1305 2.1041 REM Highest difference peak 0.438, deepest hole -0.310, 1-sigma level 0.054 Q1 1 0.6240 0.4167 0.5116 11.00000 0.05 0.44 Q2 1 0.5847 0.4122 0.4906 11.00000 0.05 0.41 Q3 1 0.8465 0.3019 0.4865 11.00000 0.05 0.23 Q4 1 0.5195 0.0118 0.4911 11.00000 0.05 0.17 Q5 1 0.7041 0.5973 0.6471 11.00000 0.05 0.17 Q6 1 0.9542 0.4344 0.6161 11.00000 0.05 0.16 Q7 1 0.4978 0.4209 0.6395 11.00000 0.05 0.16 Q8 1 0.9128 -0.0020 0.6102 11.00000 0.05 0.15 Q9 1 0.5244 0.4986 0.4895 11.00000 0.05 0.15 Q10 1 0.6346 0.1459 0.5162 11.00000 0.05 0.15 Q11 1 0.6444 0.2169 0.7150 11.00000 0.05 0.15 Q12 1 0.4203 0.3335 0.5408 11.00000 0.05 0.15 Q13 1 0.6186 0.4865 0.6142 11.00000 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2.6310 9 3 10 0.0277 -1.0748 9 3 11 2.1812 1.1703 9 3 12 -1.3763 -0.7657 9 3 13 -0.4561 1.5631 9 3 14 1.5174 0.3648 9 3 15 1.7370 1.1295 9 3 16 -0.1314 -1.0022 9 3 17 0.5727 -0.3826 9 3 18 2.1312 0.9032 9 3 19 0.0214 0.1157 9 3 20 0.2884 -1.0903 9 3 21 0.5109 -1.0444 9 3 22 1.4947 0.3214 9 3 23 -1.0395 -0.4780 9 3 24 0.3904 -0.4924 9 3 25 0.0660 -0.3987 9 3 26 0.4439 -0.4500 9 3 27 -0.7191 -0.4677 9 3 28 0.6157 0.3950 9 3 29 0.0490 0.3139 9 3 30 -0.0822 -0.6859 9 3 31 -0.0451 -0.3974 9 3 32 0.6783 0.6900 9 3 33 0.4138 0.5708 9 3 34 -0.0260 -0.4813 9 3 35 0.1047 -0.3511 9 3 36 0.3122 0.2754 9 3 37 0.6383 0.5830 9 3 38 0.1562 -0.2119 9 3 39 -0.0360 -0.1125 9 3 40 -0.0848 -0.1640 9 4 0 -1.1320 -0.0334 9 4 1 0.1739 -0.5875 9 4 2 1.3944 -0.4521 9 4 3 1.0052 0.3847 9 4 4 -1.4179 0.7337 9 4 5 1.2131 -1.6719 9 4 6 1.2246 -0.6792 9 4 7 1.0243 0.7788 9 4 8 -1.6021 0.7613 9 4 9 1.2141 -1.9587 9 4 10 0.6151 0.2311 9 4 11 -0.0423 0.6790 9 4 12 -0.7780 0.1195 9 4 13 0.7125 -1.1316 9 4 14 -0.5181 1.1197 9 4 15 -0.8946 0.2578 9 4 16 0.6192 -0.4897 9 4 17 0.5273 0.0168 9 4 18 -1.5705 1.0364 9 4 19 -0.7741 -0.2519 9 4 20 1.3191 -0.5739 9 4 21 0.5260 0.4982 9 4 22 -1.6430 0.3906 9 4 23 -0.2223 -0.4256 9 4 24 0.8958 -0.2134 9 4 25 0.1980 0.1907 9 4 26 -0.7401 0.0051 9 4 27 -0.0237 -0.0629 9 4 28 0.0878 0.2674 9 4 29 -0.2559 -0.2947 9 4 30 0.0344 -0.0010 9 4 31 -0.1846 0.4291 9 4 32 -0.3479 0.6167 9 4 33 -0.2423 -0.4486 9 4 34 -0.0557 0.0631 9 4 35 -0.2682 0.5136 9 4 36 -0.3494 0.6594 9 4 37 0.1990 -0.2591 9 5 0 -1.9773 0.0028 9 5 1 1.1084 -0.5899 9 5 2 0.4167 -0.1237 9 5 3 -0.7261 -0.6483 9 5 4 -1.8676 0.0637 9 5 5 1.4573 -0.4960 9 5 6 0.0485 -0.4296 9 5 7 -0.6037 -1.1614 9 5 8 -1.5551 0.2353 9 5 9 1.1997 -0.2126 9 5 10 -0.4448 -0.7616 9 5 11 -0.4311 -1.9683 9 5 12 -1.0919 0.5127 9 5 13 0.3177 -0.2600 9 5 14 -0.7480 -0.7059 9 5 15 -0.0391 -2.3390 9 5 16 -0.6153 0.7321 9 5 17 -0.5239 -0.8664 9 5 18 -0.7138 -0.2280 9 5 19 0.1374 -1.8463 9 5 20 -0.2542 0.6954 9 5 21 -0.7631 -1.3339 9 5 22 -0.4428 0.2638 9 5 23 -0.2210 -0.8147 9 5 24 -0.0340 0.3594 9 5 25 -0.4988 -1.0314 9 5 26 -0.1486 0.5368 9 5 27 -0.6453 0.0274 9 5 28 0.0677 -0.0723 9 5 29 -0.1915 -0.3935 9 5 30 0.0111 0.6323 9 5 31 -0.5039 0.2103 9 6 0 -0.9687 -0.0175 9 6 1 1.1569 -0.4359 9 6 2 -0.8105 0.3035 9 6 3 -1.3002 -0.3118 9 6 4 -0.6063 -0.8678 9 6 5 0.9106 -0.4497 9 6 6 -0.4677 0.4568 9 6 7 -1.2234 -0.1435 9 6 8 0.0515 -1.3129 9 6 9 0.5971 -0.4896 9 6 10 0.3128 -0.0963 9 6 11 -0.8637 -0.2742 9 6 12 0.3366 -1.1796 9 6 13 0.1843 -0.5553 9 6 14 1.1962 -0.6117 9 6 15 -0.3797 -0.7549 9 6 16 0.2249 -0.6622 9 6 17 -0.1735 -0.5299 9 6 18 1.4799 -0.5254 9 6 19 0.0499 -1.1351 9 6 20 0.1082 -0.1633 9 6 21 -0.2731 -0.3944 9 6 22 0.9381 -0.1249 10 0 0 0.5401 -0.0265 10 0 1 -0.8472 0.8721 10 0 2 0.0064 0.4285 10 0 3 0.7766 0.7513 10 0 4 0.4189 -0.0212 10 0 5 -0.4145 0.4216 10 0 6 0.0026 0.8676 10 0 7 -0.2222 -0.2330 10 0 8 0.0921 -0.0064 10 0 9 -0.5559 0.5345 10 0 10 -0.0068 0.6515 10 0 11 -0.7866 -0.7875 10 0 12 -0.3557 0.0038 10 0 13 -1.0407 1.0178 10 0 14 -0.0080 0.3148 10 0 15 0.0772 0.0760 10 0 16 -0.7432 0.0041 10 0 17 -0.8401 0.8389 10 0 18 -0.0008 0.1087 10 0 19 1.4319 1.4276 10 0 20 -0.7637 0.0006 10 0 21 -0.0998 0.1088 10 0 22 0.0034 -0.2814 10 0 23 1.8574 1.8536 10 0 24 -0.3096 -0.0010 10 0 25 0.0859 -0.0894 10 0 26 0.0016 -0.7720 10 0 27 1.3736 1.3775 10 0 28 0.2374 -0.0017 10 0 29 -0.4252 0.4083 10 0 30 -0.0001 -0.6511 10 0 31 0.9012 0.9200 10 0 32 0.4371 -0.0025 10 0 33 -0.6895 0.6722 10 0 34 0.0013 0.2048 10 0 35 0.6958 0.7272 10 1 0 -1.0053 0.0558 10 1 1 1.7868 1.6125 10 1 2 -1.3979 -0.2191 10 1 3 -1.7727 1.3323 10 1 4 -0.3384 -1.3747 10 1 5 1.3192 1.2983 10 1 6 -1.3363 -0.9851 10 1 7 -1.5621 0.6916 10 1 8 0.7177 -1.8849 10 1 9 0.3746 0.7066 10 1 10 -0.9060 -1.9261 10 1 11 -1.2999 0.1657 10 1 12 0.8423 -1.1840 10 1 13 -0.3946 0.3314 10 1 14 -0.2757 -1.8863 10 1 15 -0.9518 -0.0664 10 1 16 0.1800 0.1305 10 1 17 -0.2922 0.3277 10 1 18 -0.0354 -0.7771 10 1 19 -0.4948 -0.1214 10 1 20 -0.2833 1.1049 10 1 21 0.4922 0.4723 10 1 22 -0.2233 0.0779 10 1 23 -0.0255 -0.0697 10 1 24 -0.3445 1.2645 10 1 25 1.0024 0.4906 10 1 26 -0.1892 -0.0274 10 1 27 0.2148 0.0448 10 1 28 -0.4631 0.8428 10 1 29 0.6719 0.3374 10 1 30 0.3330 -0.3177 10 1 31 0.0399 0.0668 10 1 32 -0.6494 0.2964 10 1 33 -0.0587 0.1864 10 1 34 0.7530 -0.0865 10 2 0 -1.0230 -0.0468 10 2 1 -1.2086 -0.1054 10 2 2 -5.4982 0.4404 10 2 3 0.9712 -0.7845 10 2 4 -0.6111 0.8683 10 2 5 -0.9737 1.0781 10 2 6 -2.8461 0.5111 10 2 7 0.6855 -0.7356 10 2 8 0.1073 0.4694 10 2 9 -0.2815 1.7534 10 2 10 0.0451 -0.4094 10 2 11 0.3672 -0.4947 10 2 12 0.3597 -0.5983 10 2 13 0.0500 1.2159 10 2 14 1.1728 -1.0655 10 2 15 -0.0559 -0.3219 10 2 16 0.1974 -0.7887 10 2 17 -0.4093 -0.0291 10 2 18 0.8095 -0.6620 10 2 19 -0.1783 -0.0472 10 2 20 0.1627 0.0285 10 2 21 -0.9383 -0.8481 10 2 22 0.3575 0.0922 10 2 23 0.2401 0.3333 10 2 24 0.3354 0.6244 10 2 25 -0.7666 -0.6977 10 2 26 0.3864 0.2662 10 2 27 0.6290 0.5092 10 2 28 0.3626 0.3893 10 2 29 -0.1977 0.0106 10 2 30 0.4709 -0.0641 10 2 31 0.4066 0.3402 10 2 32 0.1495 -0.0250 10 3 0 -1.0425 0.0623 10 3 1 -1.3941 -0.5457 10 3 2 1.3755 -0.4050 10 3 3 0.3154 0.5238 10 3 4 -0.9739 -0.8103 10 3 5 -1.1238 -0.7886 10 3 6 -0.5152 -0.6274 10 3 7 -0.6244 1.4481 10 3 8 -0.4585 -0.4346 10 3 9 0.3925 -0.4703 10 3 10 -1.9854 -0.0719 10 3 11 -0.4759 1.2250 10 3 12 0.6177 0.5882 10 3 13 1.4595 -0.4799 10 3 14 -1.5539 0.4738 10 3 15 0.0436 0.1584 10 3 16 1.3811 0.8842 10 3 17 1.2138 -0.9049 10 3 18 -0.1680 0.5408 10 3 19 0.0308 -0.5893 10 3 20 1.0184 0.3932 10 3 21 0.5272 -0.9663 10 3 22 0.5886 0.4980 10 3 23 -0.3278 -0.4406 10 3 24 0.0244 0.0773 10 3 25 0.2981 -0.2953 10 3 26 0.4802 0.6046 10 3 27 -0.4099 0.1572 10 3 28 -0.5039 0.2265 10 3 29 0.2689 0.4693 10 4 0 -0.4964 0.0096 10 4 1 -0.6625 -0.3272 10 4 2 0.5500 0.0278 10 4 3 1.6069 -1.4748 10 4 4 -0.3824 -0.4883 10 4 5 -0.3582 0.0796 10 4 6 0.3011 -0.0198 10 4 7 2.1944 -2.3716 10 4 8 -0.2906 -0.3477 10 4 9 -0.7883 -0.0655 10 4 10 0.2416 -0.1242 10 4 11 1.7787 -1.9345 10 4 12 -0.5574 0.2057 10 4 13 -1.0655 -0.1286 10 4 14 0.5205 -0.1294 10 4 15 0.7906 -0.6050 10 4 16 -0.9395 0.5436 10 4 17 -0.6692 -0.1005 10 4 18 0.7178 0.0797 10 4 19 0.0065 0.3193 10 4 20 -0.9086 0.5291 10 4 21 -0.0934 -0.1927 10 4 22 0.4780 0.3237 10 4 23 -0.2947 0.4057 10 5 0 -0.6707 0.0087 10 5 1 0.9823 -1.0104 10 5 2 0.3291 -0.1279 10 5 3 -0.2553 -0.7285 10 5 4 -0.6569 -0.0716 10 5 5 1.2432 -1.2176 10 5 6 0.4495 -0.1352 10 5 7 0.4076 -0.3549 10 5 8 -0.5763 -0.2588 10 5 9 1.0029 -1.2459 10 5 10 0.2033 0.2609 10 5 11 0.4824 -0.0297 10 5 12 -0.3352 -0.4151 10 5 13 0.5675 -0.9726 11 0 1 0.1506 0.1587 11 0 2 0.1418 0.0247 11 0 3 0.1949 -0.1912 11 0 4 0.0030 -0.6169 11 0 5 0.1625 0.1666 11 0 6 0.4682 0.0090 11 0 7 0.4357 -0.4372 11 0 8 -0.0021 -1.1204 11 0 9 0.1884 0.1928 11 0 10 0.5476 -0.0041 11 0 11 0.1746 -0.1795 11 0 12 -0.0054 -0.9352 11 0 13 0.6425 0.6459 11 0 14 0.3810 -0.0063 11 0 15 -0.1277 0.1289 11 0 16 -0.0068 0.1256 11 0 17 1.0905 1.0894 11 0 18 0.5318 -0.0059 11 0 19 0.0742 -0.0690 11 0 20 -0.0033 1.1109 11 1 0 0.1715 -0.0059 11 1 1 0.2020 -0.6111 11 1 2 0.6556 0.0456 11 1 3 0.1272 -0.3265 11 1 4 0.1194 0.1742 11 1 5 0.8179 -0.8012 11 1 6 0.7521 0.0770 11 1 7 0.1908 -0.0308 11 1 8 -0.0417 -0.0265 11 1 9 1.1955 -0.7169 11 1 10 0.3949 -0.0163 11 1 11 0.1126 0.2186 11 1 12 -0.2564 -0.2475 11 1 13 0.8885 -0.3460 11 1 14 -0.2857 -0.1016 11 1 15 -0.1479 0.4260 11 1 16 -0.3761 -0.0438 11 1 17 0.2048 0.0686 11 2 0 0.0324 0.0173 11 2 1 0.0829 -0.1500 11 2 2 -0.3813 0.6144 11 2 3 -1.1450 -0.0277 11 2 4 0.2588 -0.0186 11 2 5 -1.0753 0.0806 11 2 6 0.0639 1.3891 11 2 7 -1.0896 0.2489 11 2 8 0.5417 -0.0541 11 2 9 -1.1851 0.1285 11 2 10 0.4337 1.1729 11 2 11 -0.3115 0.2016 11 2 12 0.3382 0.0294 11 2 13 -0.4807 -0.2703 0 0 0 0.0 0.0 ; _shelx_fab_checksum 88943 _olex2_date_sample_data_collection 2019-01-10 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-y+1/2, x+1/2, z+3/4' '-x, -y, z+1/2' 'y+1/2, -x+1/2, z+1/4' 'x+1/2, -y+1/2, -z+1/4' '-x+1/2, y+1/2, -z+3/4' 'y, x, -z' '-y, -x, -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 O1 O 0.8409(3) 0.2808(4) 0.64325(6) 0.0645(9) Uani 1 1 d . . . . . O2 O 0.6185(4) 0.3641(4) 0.65127(6) 0.0612(9) Uani 1 1 d . . . . . N1 N 0.7389(5) 0.2544(4) 0.58230(6) 0.0571(9) Uani 1 1 d . . . . . N2 N 0.6541(4) 0.2557(5) 0.61961(6) 0.0552(9) Uani 1 1 d . . . . . H2 H 0.565131 0.273096 0.617281 0.066 Uiso 1 1 calc R . . . . C0AA C 0.6693(6) 0.2165(7) 0.56283(9) 0.0689(13) Uani 1 1 d . . . . . H0AA H 0.604572 0.141621 0.561451 0.083 Uiso 1 1 calc R . . . . C2 C 0.7099(7) 0.3048(6) 0.54612(9) 0.0712(14) Uani 1 1 d . . . . . C3 C 0.8142(7) 0.4044(6) 0.55547(9) 0.0702(14) Uani 1 1 d . . . . . C4 C 0.8933(10) 0.5175(7) 0.54751(13) 0.097(2) Uani 1 1 d . . . . . H4 H 0.885004 0.545546 0.532848 0.116 Uiso 1 1 calc R . . . . C5 C 0.9840(10) 0.5878(8) 0.56145(14) 0.101(3) Uani 1 1 d . . . . . H5 H 1.040171 0.661272 0.555840 0.122 Uiso 1 1 calc R . . . . C6 C 0.9952(8) 0.5543(7) 0.58327(13) 0.090(2) Uani 1 1 d . . . . . H6 H 1.056831 0.606313 0.592240 0.108 Uiso 1 1 calc R . . . . C7 C 0.9152(6) 0.4427(6) 0.59229(10) 0.0696(14) Uani 1 1 d . . . . . H7 H 0.920798 0.419476 0.607183 0.083 Uiso 1 1 calc R . . . . C8 C 0.8279(6) 0.3688(5) 0.57807(8) 0.0594(11) Uani 1 1 d . . . . . C9 C 0.6598(11) 0.2954(9) 0.52309(12) 0.102(2) Uani 1 1 d . . . . . C10 C 0.752(2) 0.3321(16) 0.5056(2) 0.185(5) Uani 1 1 d . U . . . H10 H 0.845867 0.361979 0.507996 0.222 Uiso 1 1 calc R . . . . C11 C 0.687(2) 0.319(2) 0.4819(2) 0.189(6) Uani 1 1 d . U . . . H11 H 0.739691 0.339716 0.469297 0.226 Uiso 1 1 calc R . . . . C12 C 0.554(2) 0.2775(19) 0.4811(3) 0.180(6) Uani 1 1 d . U . . . H12 H 0.502426 0.303782 0.468654 0.216 Uiso 1 1 calc R . . . . C13 C 0.4889(19) 0.2056(19) 0.4954(3) 0.190(6) Uani 1 1 d . U . . . H13 H 0.411650 0.147567 0.491782 0.228 Uiso 1 1 calc R . . . . C14 C 0.5397(16) 0.2177(16) 0.51765(18) 0.158(4) Uani 1 1 d . U . . . H14 H 0.489788 0.171311 0.528821 0.190 Uiso 1 1 calc R . . . . C15 C 0.7355(5) 0.1793(5) 0.60327(8) 0.0533(10) Uani 1 1 d . . . . . H15 H 0.833930 0.171111 0.608633 0.064 Uiso 1 1 calc R . . . . C16 C 0.6782(5) 0.0336(5) 0.60049(9) 0.0606(12) Uani 1 1 d . . . . . C17 C 0.6308(6) -0.0849(6) 0.59919(10) 0.0654(13) Uani 1 1 d . . . . . C18 C 0.5714(6) -0.2233(5) 0.59687(11) 0.0685(14) Uani 1 1 d . . . . . C20 C 0.4958(10) -0.4425(8) 0.58267(19) 0.111(3) Uani 1 1 d . U . . . H20 H 0.486046 -0.523784 0.573956 0.133 Uiso 0.5 1 calc R . P A 1 H20A H 0.479044 -0.505713 0.571107 0.133 Uiso 0.3 1 calc R . P B 2 C21 C 0.4291(10) -0.4309(9) 0.60100(17) 0.107(3) Uani 1 1 d . U . . . H21 H 0.350509 -0.483963 0.605582 0.129 Uiso 0.7 1 calc R . P C 1 H21A H 0.371407 -0.505173 0.605950 0.129 Uiso 0.5 1 calc R . P D 2 C22 C 0.7160(5) 0.3007(5) 0.63867(8) 0.0548(10) Uani 1 1 d . . . . . C23 C 0.6594(6) 0.4217(6) 0.67345(10) 0.0709(14) Uani 1 1 d . . . . . C24 C 0.7681(8) 0.5358(9) 0.67101(16) 0.110(3) Uani 1 1 d . . . . . H24A H 0.856195 0.494799 0.665921 0.166 Uiso 1 1 calc GR . . . . H24B H 0.783384 0.581352 0.685004 0.166 Uiso 1 1 calc GR . . . . H24C H 0.735160 0.605243 0.660510 0.166 Uiso 1 1 calc GR . . . . C25 C 0.5182(7) 0.4853(9) 0.68110(12) 0.094(2) Uani 1 1 d . . . . . H25A H 0.489815 0.559972 0.671163 0.141 Uiso 1 1 calc GR . . . . H25B H 0.529240 0.523840 0.695675 0.141 Uiso 1 1 calc GR . . . . H25C H 0.446284 0.412038 0.681281 0.141 Uiso 1 1 calc GR . . . . C26 C 0.7051(9) 0.3028(9) 0.68783(11) 0.097(2) Uani 1 1 d . . . . . H26A H 0.633520 0.229285 0.687698 0.145 Uiso 1 1 calc GR . . . . H26B H 0.717580 0.337270 0.702623 0.145 Uiso 1 1 calc GR . . . . H26C H 0.793847 0.264550 0.682514 0.145 Uiso 1 1 calc GR . . . . S1 S 0.5942(9) -0.3163(8) 0.57534(12) 0.118(2) Uani 0.5 1 d . U P E 1 C19 C 0.5046(14) -0.3120(18) 0.6139(3) 0.076(4) Uani 0.7 1 d . U P E 1 H19 H 0.507393 -0.299109 0.629104 0.091 Uiso 0.7 1 calc R . P E 1 S1' S 0.4451(6) -0.2875(7) 0.61551(11) 0.0860(14) Uani 0.5 1 d . U P E 2 C19' C 0.610(4) -0.327(4) 0.5845(5) 0.076(8) Uani 0.3 1 d . U P E 2 H19' H 0.697837 -0.331162 0.577459 0.092 Uiso 0.3 1 calc R . P E 2 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 0.0406(16) 0.067(2) 0.086(2) -0.0115(17) -0.0064(15) 0.0080(15) O2 0.0479(18) 0.062(2) 0.0740(19) -0.0084(16) 0.0019(15) 0.0086(15) N1 0.055(2) 0.053(2) 0.063(2) -0.0047(17) -0.0008(17) -0.0002(17) N2 0.0387(18) 0.061(2) 0.066(2) -0.0012(18) 0.0008(15) 0.0035(17) C0AA 0.069(3) 0.065(3) 0.072(3) -0.008(2) -0.006(2) 0.004(3) C2 0.083(4) 0.061(3) 0.070(3) -0.002(2) 0.004(3) 0.020(3) C3 0.082(4) 0.057(3) 0.072(3) -0.001(2) 0.019(3) 0.011(3) C4 0.131(7) 0.067(4) 0.093(4) 0.007(3) 0.041(4) -0.008(4) C5 0.126(7) 0.067(4) 0.111(5) -0.001(4) 0.040(5) -0.031(4) C6 0.099(5) 0.058(3) 0.113(5) -0.010(3) 0.020(4) -0.025(3) C7 0.070(3) 0.057(3) 0.082(3) -0.004(3) 0.007(3) -0.010(3) C8 0.061(3) 0.048(2) 0.069(3) -0.002(2) 0.008(2) 0.001(2) C9 0.141(7) 0.088(5) 0.076(4) -0.010(3) 0.000(4) 0.015(5) C10 0.231(11) 0.186(10) 0.139(8) 0.000(7) 0.014(8) -0.013(9) C11 0.219(11) 0.202(11) 0.145(8) 0.010(8) 0.013(9) -0.014(10) C12 0.194(11) 0.187(11) 0.161(9) 0.024(8) -0.022(9) 0.009(9) C13 0.206(11) 0.202(11) 0.163(9) -0.033(9) -0.016(9) -0.009(9) C14 0.182(9) 0.188(10) 0.104(6) -0.029(6) -0.023(6) -0.025(8) C15 0.040(2) 0.046(2) 0.074(3) -0.001(2) 0.0015(19) -0.0029(18) C16 0.047(2) 0.047(2) 0.088(3) 0.001(2) 0.002(2) -0.001(2) C17 0.057(3) 0.050(3) 0.089(3) 0.003(2) -0.006(3) 0.002(2) C18 0.058(3) 0.040(2) 0.107(4) 0.006(3) -0.006(3) 0.004(2) C20 0.107(5) 0.066(4) 0.160(7) -0.028(4) -0.010(5) -0.006(4) C21 0.101(5) 0.076(4) 0.145(6) 0.026(4) -0.014(5) -0.032(4) C22 0.045(2) 0.046(2) 0.074(3) 0.0032(19) 0.006(2) 0.0053(18) C23 0.062(3) 0.069(3) 0.081(3) -0.019(3) 0.000(3) -0.009(3) C24 0.076(4) 0.102(5) 0.153(7) -0.049(5) 0.026(5) -0.035(4) C25 0.071(4) 0.106(5) 0.104(5) -0.048(4) 0.012(3) -0.011(4) C26 0.096(5) 0.117(6) 0.078(4) -0.009(4) -0.016(3) 0.009(4) S1 0.134(5) 0.079(3) 0.141(5) -0.024(4) 0.023(4) -0.004(3) C19 0.072(7) 0.069(7) 0.087(6) 0.013(5) 0.003(6) -0.025(6) S1' 0.090(3) 0.071(3) 0.097(3) 0.0088(18) 0.010(3) -0.020(3) C19' 0.073(11) 0.066(11) 0.090(13) 0.004(11) 0.009(10) -0.001(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' 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' S S 0.3331 0.5567 '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 C22 O2 C23 120.1(4) . . ? C0AA N1 C8 108.8(4) . . ? C0AA N1 C15 127.4(4) . . ? C8 N1 C15 123.4(4) . . ? C22 N2 C15 120.9(4) . . ? C2 C0AA N1 110.2(5) . . ? C0AA C2 C3 106.5(5) . . ? C0AA C2 C9 125.4(7) . . ? C3 C2 C9 128.0(6) . . ? C4 C3 C2 135.3(6) . . ? C4 C3 C8 118.1(6) . . ? C8 C3 C2 106.6(5) . . ? C5 C4 C3 119.1(7) . . ? C6 C5 C4 122.5(6) . . ? C5 C6 C7 120.7(7) . . ? C8 C7 C6 116.7(6) . . ? N1 C8 C3 107.9(5) . . ? C7 C8 N1 129.3(5) . . ? C7 C8 C3 122.8(5) . . ? C10 C9 C2 120.1(11) . . ? C14 C9 C2 121.1(8) . . ? C14 C9 C10 116.7(10) . . ? C9 C10 C11 115.5(15) . . ? C12 C11 C10 115.5(16) . . ? C13 C12 C11 126.7(18) . . ? C12 C13 C14 116.4(17) . . ? C9 C14 C13 122.5(14) . . ? N1 C15 C16 110.8(4) . . ? N2 C15 N1 111.9(4) . . ? N2 C15 C16 110.2(4) . . ? C17 C16 C15 177.2(6) . . ? C16 C17 C18 177.6(6) . . ? C17 C18 S1 122.1(6) . . ? C17 C18 C19 128.0(9) . . ? C17 C18 S1' 121.2(5) . . ? C19 C18 S1 109.1(8) . . ? C19' C18 C17 130.0(18) . . ? C19' C18 S1' 108.0(17) . . ? C21 C20 S1 118.0(7) . . ? C21 C20 C19' 102.5(15) . . ? C20 C21 C19 106.3(9) . . ? C20 C21 S1' 120.0(7) . . ? O1 C22 O2 126.6(5) . . ? O1 C22 N2 123.8(4) . . ? O2 C22 N2 109.5(4) . . ? O2 C23 C24 110.2(6) . . ? O2 C23 C25 101.1(5) . . ? O2 C23 C26 109.4(5) . . ? C24 C23 C25 110.2(6) . . ? C26 C23 C24 113.8(7) . . ? C26 C23 C25 111.5(6) . . ? C20 S1 C18 95.9(6) . . ? C18 C19 C21 104.4(12) . . ? C21 S1' C18 89.8(5) . . ? C18 C19' C20 113(3) . . ? 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 C22 1.216(6) . ? O2 C22 1.329(6) . ? O2 C23 1.499(7) . ? N1 C0AA 1.393(7) . ? N1 C8 1.380(7) . ? N1 C15 1.452(6) . ? N2 C15 1.439(6) . ? N2 C22 1.359(6) . ? C0AA C2 1.361(8) . ? C2 C3 1.463(9) . ? C2 C9 1.475(9) . ? C3 C4 1.378(9) . ? C3 C8 1.416(8) . ? C4 C5 1.366(12) . ? C5 C6 1.363(11) . ? C6 C7 1.396(8) . ? C7 C8 1.374(8) . ? C9 C10 1.411(16) . ? C9 C14 1.378(16) . ? C10 C11 1.56(2) . ? C11 C12 1.31(2) . ? C12 C13 1.26(2) . ? C13 C14 1.433(18) . ? C15 C16 1.475(7) . ? C16 C17 1.196(7) . ? C17 C18 1.416(8) . ? C18 S1 1.583(9) . ? C18 C19 1.464(17) . ? C18 S1' 1.742(8) . ? C18 C19' 1.27(4) . ? C20 C21 1.279(13) . ? C20 S1 1.562(13) . ? C20 C19' 1.52(4) . ? C21 C19 1.532(19) . ? C21 S1' 1.611(12) . ? C23 C24 1.482(9) . ? C23 C25 1.521(9) . ? C23 C26 1.476(10) . ? loop_ _smtbx_masks_void_nr _smtbx_masks_void_average_x _smtbx_masks_void_average_y _smtbx_masks_void_average_z _smtbx_masks_void_volume _smtbx_masks_void_count_electrons _smtbx_masks_void_content 1 0.131 0.131 0.000 241.7 43.4 ? 2 -0.131 -0.131 0.500 241.7 43.4 ? 3 -0.369 0.369 0.250 241.7 43.4 ? 4 0.369 0.631 0.750 241.7 43.4 ?