#------------------------------------------------------------------------------ #$Date: 2018-07-12 00:58:36 +0300 (Thu, 12 Jul 2018) $ #$Revision: 208982 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/19/7121949.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_7121949 loop_ _publ_author_name 'Zhao, Qian' 'Peng, Cheng' 'Huang, Hua' 'Liu, Shuai-Jiang' 'Zhong, Ya-Jun' 'Huang, Wei' 'He, Gu' 'Han, Bo' _publ_section_title ; Asymmetric synthesis of tetrahydroisoquinoline-fused spirooxindoles as Ras-GTP inhibitors that inhibit colon adenocarcinoma cell proliferation and invasion ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/C8CC04732D _journal_year 2018 _chemical_formula_moiety 'C29 H28 N4 O8, C4 H8 O2' _chemical_formula_sum 'C33 H36 N4 O10' _chemical_formula_weight 648.66 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2018-04-18 _audit_creation_method ; Olex2 1.2 (compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381) ; _audit_update_record ; 2018-06-10 deposited with the CCDC. 2018-07-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.3385(17) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.4543(2) _cell_length_b 13.8322(3) _cell_length_c 23.1289(5) _cell_measurement_reflns_used 5693 _cell_measurement_temperature 295.12(15) _cell_measurement_theta_max 72.3620 _cell_measurement_theta_min 4.6090 _cell_volume 3344.52(12) _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 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment air _diffrn_ambient_temperature 295.12(15) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 7.9797 _diffrn_detector_type EosS2 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.974 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 25.00 103.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.0421 57.0000 -60.0000 78 #__ type_ start__ end____ width___ exp.time_ 2 omega 106.00 155.00 1.0000 3.0700 omega____ theta____ kappa____ phi______ frames - 108.0000 61.0000 -150.0000 49 #__ type_ start__ end____ width___ exp.time_ 3 omega 113.00 150.00 1.0000 3.0700 omega____ theta____ kappa____ phi______ frames - 108.0000 30.0000 -30.0000 37 #__ type_ start__ end____ width___ exp.time_ 4 omega 92.00 162.00 1.0000 3.0700 omega____ theta____ kappa____ phi______ frames - 108.0000 45.0000 -180.0000 70 #__ type_ start__ end____ width___ exp.time_ 5 omega 70.00 104.00 1.0000 3.0700 omega____ theta____ kappa____ phi______ frames - 108.0000 -94.0000 -180.0000 34 #__ type_ start__ end____ width___ exp.time_ 6 omega 43.00 70.00 1.0000 3.0700 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 -180.0000 27 #__ type_ start__ end____ width___ exp.time_ 7 omega 2.00 70.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.0421 -99.0000 -150.0000 68 #__ type_ start__ end____ width___ exp.time_ 8 omega 2.00 53.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.0421 -99.0000 0.0000 51 #__ type_ start__ end____ width___ exp.time_ 9 omega 38.00 63.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.0421 -77.0000 0.0000 25 #__ type_ start__ end____ width___ exp.time_ 10 omega 9.00 52.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.0421 -57.0000 60.0000 43 #__ type_ start__ end____ width___ exp.time_ 11 omega 4.00 60.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.0421 -99.0000 120.0000 56 #__ type_ start__ end____ width___ exp.time_ 12 omega 38.00 80.00 1.0000 3.0700 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 60.0000 42 #__ type_ start__ end____ width___ exp.time_ 13 omega 45.00 85.00 1.0000 3.0700 omega____ theta____ kappa____ phi______ frames - 108.0000 -61.0000 120.0000 40 #__ type_ start__ end____ width___ exp.time_ 14 omega 100.00 126.00 1.0000 3.0700 omega____ theta____ kappa____ phi______ frames - 108.0000 -61.0000 120.0000 26 #__ type_ start__ end____ width___ exp.time_ 15 omega 42.00 107.00 1.0000 3.0700 omega____ theta____ kappa____ phi______ frames - 108.0000 -94.0000 90.0000 65 #__ type_ start__ end____ width___ exp.time_ 16 omega 41.00 72.00 1.0000 3.0700 omega____ theta____ kappa____ phi______ frames - 108.0000 -45.0000 150.0000 31 #__ type_ start__ end____ width___ exp.time_ 17 omega -27.00 4.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.0421 -57.0000 60.0000 31 #__ type_ start__ end____ width___ exp.time_ 18 omega -32.00 11.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.0421 -38.0000 -60.0000 43 #__ type_ start__ end____ width___ exp.time_ 19 omega 109.00 134.00 1.0000 3.0700 omega____ theta____ kappa____ phi______ frames - 108.0000 178.0000 150.0000 25 #__ type_ start__ end____ width___ exp.time_ 20 omega 78.00 104.00 1.0000 3.0700 omega____ theta____ kappa____ phi______ frames - 108.0000 178.0000 150.0000 26 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'New Gemini, Dual, Cu at zero, EosS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0377714000 _diffrn_orient_matrix_UB_12 -0.1034783000 _diffrn_orient_matrix_UB_13 0.0176533000 _diffrn_orient_matrix_UB_21 -0.1246553000 _diffrn_orient_matrix_UB_22 0.0388493000 _diffrn_orient_matrix_UB_23 0.0265176000 _diffrn_orient_matrix_UB_31 -0.0688508000 _diffrn_orient_matrix_UB_32 -0.0137391000 _diffrn_orient_matrix_UB_33 -0.0585105000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_unetI/netI 0.0316 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.974 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 12960 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.974 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 72.502 _diffrn_reflns_theta_min 4.229 _diffrn_source 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.804 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.71493 _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 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.288 _exptl_crystal_description block _exptl_crystal_F_000 1368 _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.35 _refine_diff_density_max 0.405 _refine_diff_density_min -0.535 _refine_diff_density_rms 0.150 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 431 _refine_ls_number_reflns 6464 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.0875 _refine_ls_R_factor_gt 0.0782 _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^)+(0.1380P)^2^+0.6843P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2011 _refine_ls_wR_factor_ref 0.2138 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5300 _reflns_number_total 6464 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c8cc04732d2.cif _cod_data_source_block lq-0410 _cod_database_code 7121949 _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. ; _reflns_odcompleteness_completeness 99.87 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Ternary CH refined with riding coordinates: C1(H1A) 2.b Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C22(H22A,H22B), C31(H31A,H31B) 2.c Aromatic/amide H refined with riding coordinates: C5(H5), C3(H3), C11(H11), C14(H14), C13(H13), C28(H28), C24(H24), C26(H26), C27(H27), C25(H25) 2.d Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B, H21C), C29(H29A,H29B,H29C), C32(H32A,H32B,H32C) 2.e Idealised tetrahedral OH refined as rotating group: O1(H1) ; _shelx_res_file ; lq-0410.res created by SHELXL-2014/7 TITL lq-0410_a.res in P2(1)/c REM Old TITL lq-0410 in P21/c #14 REM SHELXT solution in P2(1)/c REM R1 0.246, Rweak 0.131, Alpha 0.054, Orientation as input REM Formula found by SHELXT: C36 N3 O7 CELL 1.54184 10.454288 13.832209 23.128924 90 90.3385 90 ZERR 4 0.000213 0.000286 0.000455 0 0.0017 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 132 144 16 40 L.S. 10 PLAN 20 BOND $H LIST 6 fmap 2 acta REM REM REM WGHT 0.138000 0.684300 FVAR 4.92517 O8 4 0.934918 0.254144 0.420439 11.00000 0.04636 0.04248 = 0.06764 -0.01229 -0.00665 0.00567 O1 4 0.725318 0.449243 0.535989 11.00000 0.06852 0.07074 = 0.04576 -0.00294 -0.00675 0.01910 AFIX 147 H1 2 0.774209 0.419623 0.557446 11.00000 -1.50000 AFIX 0 O6 4 0.736517 0.342668 0.327685 11.00000 0.06823 0.05454 = 0.05014 0.01057 -0.00232 -0.00424 O7 4 1.014103 0.367691 0.481572 11.00000 0.04358 0.05221 = 0.09552 -0.01942 -0.02021 0.00330 N1 3 0.805770 0.368609 0.452908 11.00000 0.03887 0.03371 = 0.05265 -0.00392 -0.00787 0.00030 O4 4 0.317853 0.542654 0.333596 11.00000 0.05541 0.10752 = 0.07602 0.01487 -0.01405 0.02156 N4 3 0.684508 0.190290 0.359837 11.00000 0.06009 0.04583 = 0.04523 -0.00295 -0.00976 -0.00782 N3 3 0.395086 0.486212 0.353887 11.00000 0.04530 0.07775 = 0.05257 0.00485 -0.00435 0.01027 C17 1 0.927565 0.331867 0.454303 11.00000 0.04255 0.03638 = 0.05642 -0.00109 -0.00471 0.00013 O5 4 0.386847 0.400429 0.348128 11.00000 0.09246 0.07065 = 0.12691 0.00186 -0.05576 -0.00632 C2 1 0.692608 0.519457 0.444067 11.00000 0.04789 0.03932 = 0.04701 -0.00386 -0.00244 0.00765 C6 1 0.507289 0.527154 0.383883 11.00000 0.04330 0.05494 = 0.04395 -0.00108 0.00139 0.01198 C15 1 0.671355 0.144918 0.413742 11.00000 0.04600 0.04258 = 0.05261 0.00102 -0.00819 -0.00594 C1 1 0.782220 0.460522 0.481343 11.00000 0.04584 0.03742 = 0.05266 -0.00577 -0.00772 0.00313 AFIX 13 H1A 2 0.863321 0.495329 0.485832 11.00000 -1.20000 AFIX 0 C7 1 0.587015 0.472689 0.419660 11.00000 0.04096 0.04615 = 0.04439 -0.00122 0.00148 0.00799 O3 4 0.587398 0.812250 0.355252 11.00000 0.15426 0.05523 = 0.13119 0.02410 -0.03723 0.01966 C10 1 0.682876 0.212726 0.457797 11.00000 0.04096 0.04008 = 0.04986 0.00305 -0.00699 -0.00295 C8 1 0.571842 0.368770 0.437582 11.00000 0.03968 0.04849 = 0.05309 0.00549 -0.00383 -0.00063 AFIX 23 H8A 2 0.505654 0.338813 0.414105 11.00000 -1.20000 H8B 2 0.544858 0.366181 0.477606 11.00000 -1.20000 AFIX 0 C5 1 0.529382 0.624203 0.373142 11.00000 0.06399 0.05506 = 0.04928 0.00324 -0.00081 0.02344 AFIX 43 H5 2 0.474449 0.659748 0.349577 11.00000 -1.20000 AFIX 0 C16 1 0.711622 0.286587 0.365852 11.00000 0.04387 0.04395 = 0.04637 0.00348 -0.00787 -0.00278 C9 1 0.698113 0.311324 0.430836 11.00000 0.04116 0.03733 = 0.04512 0.00119 -0.00599 -0.00326 C3 1 0.717866 0.615901 0.433740 11.00000 0.06081 0.03852 = 0.05917 -0.00591 -0.00481 0.00624 AFIX 43 H3 2 0.788788 0.646092 0.450152 11.00000 -1.20000 AFIX 0 C11 1 0.680637 0.184801 0.514674 11.00000 0.04751 0.05072 = 0.04891 0.00443 -0.00466 -0.00009 AFIX 43 H11 2 0.688164 0.230617 0.543926 11.00000 -1.20000 AFIX 0 N2 3 0.660658 0.768757 0.385783 11.00000 0.11475 0.04054 = 0.09109 0.00351 -0.01714 0.01228 C4 1 0.634230 0.666212 0.398170 11.00000 0.07408 0.03937 = 0.06004 -0.00096 -0.00237 0.01362 C14 1 0.656608 0.048040 0.425885 11.00000 0.05962 0.04108 = 0.07076 -0.00216 -0.00741 -0.00840 AFIX 43 H14 2 0.648325 0.002532 0.396502 11.00000 -1.20000 AFIX 0 C23 1 0.541285 0.116341 0.288043 11.00000 0.06729 0.07482 = 0.03872 -0.01065 -0.00162 -0.01337 C12 1 0.666934 0.086800 0.528341 11.00000 0.04564 0.05756 = 0.06294 0.01629 -0.00152 0.00026 C13 1 0.654598 0.021059 0.483545 11.00000 0.05417 0.04237 = 0.08346 0.01395 -0.00413 -0.00457 AFIX 43 H13 2 0.644527 -0.044017 0.492542 11.00000 -1.20000 AFIX 0 O2 4 0.754866 0.804972 0.406546 11.00000 0.17449 0.05112 = 0.20945 0.02400 -0.08532 -0.02292 O9 4 0.874069 0.330152 0.607576 11.00000 0.14531 0.12986 = 0.08904 -0.01682 -0.04261 0.04683 C22 1 0.676680 0.140972 0.304100 11.00000 0.06721 0.06249 = 0.05004 -0.01390 -0.00257 -0.00320 AFIX 23 H22A 2 0.726976 0.082098 0.305766 11.00000 -1.20000 H22B 2 0.712852 0.182165 0.274454 11.00000 -1.20000 AFIX 0 C33 1 0.667888 0.054565 0.590223 11.00000 0.07970 0.07736 = 0.07125 0.02959 0.00125 0.00503 AFIX 137 H33A 2 0.751684 0.064070 0.606446 11.00000 -1.50000 H33B 2 0.645813 -0.012718 0.592190 11.00000 -1.50000 H33C 2 0.606780 0.091699 0.611663 11.00000 -1.50000 AFIX 0 C18 1 1.045623 0.187804 0.422556 11.00000 0.04895 0.05345 = 0.09579 -0.01484 -0.00507 0.01346 C28 1 0.506371 0.020882 0.278065 11.00000 0.12330 0.08729 = 0.04295 -0.00780 -0.00064 -0.04496 AFIX 43 H28 2 0.566046 -0.028537 0.282198 11.00000 -1.20000 AFIX 0 O10 4 0.990676 0.306685 0.684709 11.00000 0.16211 0.16290 = 0.14108 0.05688 -0.08310 -0.04157 C24 1 0.452054 0.188615 0.282022 11.00000 0.07900 0.12011 = 0.06670 -0.02013 -0.01153 0.01540 AFIX 43 H24 2 0.474302 0.252911 0.288172 11.00000 -1.20000 AFIX 0 C19 1 1.168006 0.239160 0.409053 11.00000 0.05778 0.09243 = 0.14032 -0.02858 0.02037 0.00391 AFIX 137 H19A 2 1.160023 0.271230 0.372400 11.00000 -1.50000 H19B 2 1.236653 0.193158 0.407452 11.00000 -1.50000 H19C 2 1.185776 0.286005 0.438654 11.00000 -1.50000 AFIX 0 C20 1 1.047176 0.141883 0.482092 11.00000 0.09273 0.06959 = 0.13737 0.01787 -0.01827 0.02505 AFIX 137 H20A 2 1.065625 0.190355 0.510653 11.00000 -1.50000 H20B 2 1.111758 0.092590 0.483558 11.00000 -1.50000 H20C 2 0.965130 0.113634 0.489754 11.00000 -1.50000 AFIX 0 C21 1 1.011833 0.115602 0.375702 11.00000 0.07744 0.07472 = 0.15075 -0.05363 -0.01119 0.02372 AFIX 137 H21A 2 0.933277 0.083668 0.385357 11.00000 -1.50000 H21B 2 1.079009 0.068612 0.372548 11.00000 -1.50000 H21C 2 1.001787 0.148744 0.339491 11.00000 -1.50000 AFIX 0 C26 1 0.293624 0.070423 0.255545 11.00000 0.09372 0.37233 = 0.05789 -0.00799 -0.01464 -0.09812 AFIX 43 H26 2 0.210699 0.055503 0.243820 11.00000 -1.20000 AFIX 0 C27 1 0.381590 0.000209 0.261884 11.00000 0.16213 0.19896 = 0.05238 -0.01344 -0.00749 -0.12967 AFIX 43 H27 2 0.358079 -0.063697 0.255249 11.00000 -1.20000 AFIX 0 C30 1 0.947203 0.360498 0.643320 11.00000 0.07957 0.13291 = 0.08542 0.01222 -0.01122 0.02153 C29 1 0.989159 0.460381 0.647420 11.00000 0.08792 0.12658 = 0.14995 0.03058 -0.00906 0.00408 AFIX 137 H29A 2 0.956158 0.496221 0.615069 11.00000 -1.50000 H29B 2 1.080931 0.462732 0.647221 11.00000 -1.50000 H29C 2 0.958118 0.488205 0.682679 11.00000 -1.50000 AFIX 0 C25 1 0.327633 0.163437 0.266513 11.00000 0.07247 0.27984 = 0.07340 -0.02406 -0.00870 0.02648 AFIX 43 H25 2 0.265984 0.211687 0.263572 11.00000 -1.20000 AFIX 0 C31 1 0.951042 0.203028 0.682868 11.00000 0.22939 0.14037 = 0.22861 0.06288 -0.12554 -0.06397 AFIX 23 H31A 2 0.860540 0.198467 0.691464 11.00000 -1.20000 H31B 2 0.963867 0.178129 0.644127 11.00000 -1.20000 AFIX 0 C32 1 1.016775 0.148471 0.720522 11.00000 0.31440 0.17289 = 0.30865 0.08598 -0.07151 -0.08088 AFIX 137 H32A 2 1.106518 0.153166 0.712422 11.00000 -1.50000 H32B 2 0.989944 0.082346 0.717009 11.00000 -1.50000 H32C 2 1.000987 0.170788 0.759128 11.00000 -1.50000 AFIX 0 HKLF 4 REM lq-0410_a.res in P2(1)/c REM R1 = 0.0782 for 5300 Fo > 4sig(Fo) and 0.0875 for all 6464 data REM 431 parameters refined using 0 restraints END WGHT 0.1380 0.6843 REM Highest difference peak 0.405, deepest hole -0.535, 1-sigma level 0.150 Q1 1 0.4923 0.3349 0.4391 11.00000 0.05 0.40 Q2 1 0.5000 0.5000 0.5000 10.50000 0.05 0.40 Q3 1 0.5016 0.4418 0.5102 11.00000 0.05 0.38 Q4 1 0.5002 0.2251 0.4210 11.00000 0.05 0.37 Q5 1 0.5048 0.2752 0.5381 11.00000 0.05 0.36 Q6 1 0.5047 0.2508 0.5074 11.00000 0.05 0.35 Q7 1 1.1682 0.5190 0.6249 11.00000 0.05 0.35 Q8 1 0.4752 0.2419 0.4696 11.00000 0.05 0.34 Q9 1 1.1701 0.0649 0.3281 11.00000 0.05 0.34 Q10 1 1.1388 0.4873 0.6128 11.00000 0.05 0.34 Q11 1 0.4960 0.1838 0.5497 11.00000 0.05 0.33 Q12 1 0.8217 0.4823 0.7413 11.00000 0.05 0.33 Q13 1 0.5064 0.1565 0.5653 11.00000 0.05 0.32 Q14 1 0.8181 0.0898 0.2408 11.00000 0.05 0.32 Q15 1 0.9381 0.4039 0.6022 11.00000 0.05 0.32 Q16 1 1.1711 0.4296 0.6217 11.00000 0.05 0.31 Q17 1 0.8522 0.2145 0.2914 11.00000 0.05 0.30 Q18 1 1.1279 0.4298 0.5995 11.00000 0.05 0.30 Q19 1 0.8276 0.5557 0.7271 11.00000 0.05 0.29 Q20 1 0.8331 0.0404 0.2864 11.00000 0.05 0.29 ; _shelx_res_checksum 76382 _olex2_date_sample_data_collection 2018-04-18 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn O8 O 0.93492(14) 0.25414(10) 0.42044(7) 0.0522(4) Uani 1 1 d . O1 O 0.72532(17) 0.44924(13) 0.53599(7) 0.0617(4) Uani 1 1 d . H1 H 0.7742 0.4196 0.5574 0.093 Uiso 1 1 calc GR O6 O 0.73652(16) 0.34267(12) 0.32769(7) 0.0576(4) Uani 1 1 d . O7 O 1.01410(15) 0.36769(12) 0.48157(9) 0.0638(5) Uani 1 1 d . N1 N 0.80577(15) 0.36861(11) 0.45291(7) 0.0418(4) Uani 1 1 d . O4 O 0.31785(17) 0.54265(18) 0.33360(9) 0.0797(6) Uani 1 1 d . N4 N 0.68451(18) 0.19029(13) 0.35984(7) 0.0504(4) Uani 1 1 d . N3 N 0.39509(17) 0.48621(17) 0.35389(8) 0.0586(5) Uani 1 1 d . C17 C 0.92756(18) 0.33187(14) 0.45430(9) 0.0451(4) Uani 1 1 d . O5 O 0.3868(2) 0.40043(17) 0.34813(12) 0.0969(8) Uani 1 1 d . C2 C 0.69261(19) 0.51946(14) 0.44407(9) 0.0448(4) Uani 1 1 d . C6 C 0.50729(19) 0.52715(16) 0.38388(9) 0.0474(5) Uani 1 1 d . C15 C 0.67136(19) 0.14492(15) 0.41374(9) 0.0471(5) Uani 1 1 d . C1 C 0.78222(19) 0.46052(14) 0.48134(9) 0.0453(4) Uani 1 1 d . H1A H 0.8633 0.4953 0.4858 0.054 Uiso 1 1 calc R C7 C 0.58702(18) 0.47269(14) 0.41966(8) 0.0438(4) Uani 1 1 d . O3 O 0.5874(3) 0.81225(16) 0.35525(13) 0.1137(10) Uani 1 1 d . C10 C 0.68288(18) 0.21273(14) 0.45780(9) 0.0437(4) Uani 1 1 d . C8 C 0.57184(18) 0.36877(15) 0.43758(9) 0.0471(5) Uani 1 1 d . H8A H 0.5057 0.3388 0.4141 0.057 Uiso 1 1 calc R H8B H 0.5449 0.3662 0.4776 0.057 Uiso 1 1 calc R C5 C 0.5294(2) 0.62420(17) 0.37314(10) 0.0561(5) Uani 1 1 d . H5 H 0.4744 0.6597 0.3496 0.067 Uiso 1 1 calc R C16 C 0.71162(19) 0.28659(15) 0.36585(9) 0.0448(4) Uani 1 1 d . C9 C 0.69811(17) 0.31132(13) 0.43084(8) 0.0412(4) Uani 1 1 d . C3 C 0.7179(2) 0.61590(15) 0.43374(10) 0.0529(5) Uani 1 1 d . H3 H 0.7888 0.6461 0.4502 0.063 Uiso 1 1 calc R C11 C 0.6806(2) 0.18480(16) 0.51467(9) 0.0491(5) Uani 1 1 d . H11 H 0.6882 0.2306 0.5439 0.059 Uiso 1 1 calc R N2 N 0.6607(3) 0.76876(16) 0.38578(12) 0.0822(7) Uani 1 1 d . C4 C 0.6342(2) 0.66621(16) 0.39817(10) 0.0578(6) Uani 1 1 d . C14 C 0.6566(2) 0.04804(16) 0.42589(11) 0.0572(5) Uani 1 1 d . H14 H 0.6483 0.0025 0.3965 0.069 Uiso 1 1 calc R C23 C 0.5413(2) 0.1163(2) 0.28804(9) 0.0603(6) Uani 1 1 d . C12 C 0.6669(2) 0.08680(18) 0.52834(10) 0.0554(5) Uani 1 1 d . C13 C 0.6546(2) 0.02106(17) 0.48354(12) 0.0600(6) Uani 1 1 d . H13 H 0.6445 -0.0440 0.4925 0.072 Uiso 1 1 calc R O2 O 0.7549(4) 0.80497(17) 0.40655(19) 0.1454(15) Uani 1 1 d . O9 O 0.8741(3) 0.3302(2) 0.60758(12) 0.1216(11) Uani 1 1 d . C22 C 0.6767(2) 0.14097(19) 0.30410(10) 0.0599(6) Uani 1 1 d . H22A H 0.7270 0.0821 0.3058 0.072 Uiso 1 1 calc R H22B H 0.7129 0.1822 0.2745 0.072 Uiso 1 1 calc R C33 C 0.6679(3) 0.0546(2) 0.59022(13) 0.0761(8) Uani 1 1 d . H33A H 0.7517 0.0641 0.6064 0.114 Uiso 1 1 calc GR H33B H 0.6458 -0.0127 0.5922 0.114 Uiso 1 1 calc GR H33C H 0.6068 0.0917 0.6117 0.114 Uiso 1 1 calc GR C18 C 1.0456(2) 0.18780(18) 0.42256(13) 0.0661(7) Uani 1 1 d . C28 C 0.5064(4) 0.0209(2) 0.27806(11) 0.0845(10) Uani 1 1 d . H28 H 0.5660 -0.0285 0.2822 0.101 Uiso 1 1 calc R O10 O 0.9907(4) 0.3067(3) 0.68471(17) 0.1557(17) Uani 1 1 d . C24 C 0.4521(3) 0.1886(3) 0.28202(13) 0.0886(10) Uani 1 1 d . H24 H 0.4743 0.2529 0.2882 0.106 Uiso 1 1 calc R C19 C 1.1680(3) 0.2392(3) 0.4091(2) 0.0968(11) Uani 1 1 d . H19A H 1.1600 0.2712 0.3724 0.145 Uiso 1 1 calc GR H19B H 1.2367 0.1932 0.4075 0.145 Uiso 1 1 calc GR H19C H 1.1858 0.2860 0.4387 0.145 Uiso 1 1 calc GR C20 C 1.0472(4) 0.1419(2) 0.4821(2) 0.1000(12) Uani 1 1 d . H20A H 1.0656 0.1904 0.5107 0.150 Uiso 1 1 calc GR H20B H 1.1118 0.0926 0.4836 0.150 Uiso 1 1 calc GR H20C H 0.9651 0.1136 0.4898 0.150 Uiso 1 1 calc GR C21 C 1.0118(3) 0.1156(3) 0.3757(2) 0.1010(13) Uani 1 1 d . H21A H 0.9333 0.0837 0.3854 0.152 Uiso 1 1 calc GR H21B H 1.0790 0.0686 0.3725 0.152 Uiso 1 1 calc GR H21C H 1.0018 0.1487 0.3395 0.152 Uiso 1 1 calc GR C26 C 0.2936(5) 0.0704(8) 0.25554(19) 0.175(4) Uani 1 1 d . H26 H 0.2107 0.0555 0.2438 0.210 Uiso 1 1 calc R C27 C 0.3816(6) 0.0002(5) 0.26188(15) 0.138(2) Uani 1 1 d . H27 H 0.3581 -0.0637 0.2552 0.165 Uiso 1 1 calc R C30 C 0.9472(4) 0.3605(4) 0.64332(17) 0.0993(12) Uani 1 1 d . C29 C 0.9892(4) 0.4604(4) 0.6474(2) 0.1215(15) Uani 1 1 d . H29A H 0.9562 0.4962 0.6151 0.182 Uiso 1 1 calc GR H29B H 1.0809 0.4627 0.6472 0.182 Uiso 1 1 calc GR H29C H 0.9581 0.4882 0.6827 0.182 Uiso 1 1 calc GR C25 C 0.3276(4) 0.1634(6) 0.26651(18) 0.142(2) Uani 1 1 d . H25 H 0.2660 0.2117 0.2636 0.170 Uiso 1 1 calc R C31 C 0.9510(8) 0.2030(5) 0.6829(4) 0.200(4) Uani 1 1 d . H31A H 0.8605 0.1985 0.6915 0.240 Uiso 1 1 calc R H31B H 0.9639 0.1781 0.6441 0.240 Uiso 1 1 calc R C32 C 1.0168(11) 0.1485(6) 0.7205(5) 0.266(6) Uani 1 1 d . H32A H 1.1065 0.1532 0.7124 0.398 Uiso 1 1 calc GR H32B H 0.9899 0.0823 0.7170 0.398 Uiso 1 1 calc GR H32C H 1.0010 0.1708 0.7591 0.398 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 O8 0.0464(8) 0.0425(7) 0.0676(9) -0.0123(6) -0.0067(6) 0.0057(6) O1 0.0685(10) 0.0707(11) 0.0458(8) -0.0029(7) -0.0067(7) 0.0191(8) O6 0.0682(10) 0.0545(9) 0.0501(8) 0.0106(7) -0.0023(7) -0.0042(7) O7 0.0436(8) 0.0522(9) 0.0955(13) -0.0194(8) -0.0202(8) 0.0033(6) N1 0.0389(8) 0.0337(7) 0.0526(9) -0.0039(6) -0.0079(6) 0.0003(6) O4 0.0554(10) 0.1075(16) 0.0760(12) 0.0149(11) -0.0140(8) 0.0216(10) N4 0.0601(10) 0.0458(9) 0.0452(9) -0.0030(7) -0.0098(7) -0.0078(8) N3 0.0453(9) 0.0777(14) 0.0526(10) 0.0049(9) -0.0044(8) 0.0103(9) C17 0.0425(9) 0.0364(9) 0.0564(11) -0.0011(8) -0.0047(8) 0.0001(7) O5 0.0925(15) 0.0706(13) 0.127(2) 0.0019(12) -0.0558(14) -0.0063(11) C2 0.0479(10) 0.0393(10) 0.0470(10) -0.0039(7) -0.0024(8) 0.0077(8) C6 0.0433(10) 0.0549(11) 0.0439(10) -0.0011(8) 0.0014(8) 0.0120(8) C15 0.0460(10) 0.0426(10) 0.0526(11) 0.0010(8) -0.0082(8) -0.0059(8) C1 0.0458(10) 0.0374(9) 0.0527(11) -0.0058(8) -0.0077(8) 0.0031(7) C7 0.0410(9) 0.0461(10) 0.0444(10) -0.0012(8) 0.0015(7) 0.0080(8) O3 0.154(2) 0.0552(12) 0.131(2) 0.0241(13) -0.0372(19) 0.0197(14) C10 0.0410(9) 0.0401(9) 0.0499(10) 0.0030(8) -0.0070(8) -0.0029(7) C8 0.0397(9) 0.0485(11) 0.0531(11) 0.0055(8) -0.0038(8) -0.0006(8) C5 0.0640(13) 0.0551(12) 0.0493(11) 0.0032(9) -0.0008(9) 0.0234(10) C16 0.0439(9) 0.0440(10) 0.0464(10) 0.0035(8) -0.0079(8) -0.0028(8) C9 0.0412(9) 0.0373(9) 0.0451(9) 0.0012(7) -0.0060(7) -0.0033(7) C3 0.0608(12) 0.0385(10) 0.0592(12) -0.0059(9) -0.0048(10) 0.0062(9) C11 0.0475(10) 0.0507(11) 0.0489(10) 0.0044(8) -0.0047(8) -0.0001(8) N2 0.115(2) 0.0405(11) 0.0911(17) 0.0035(11) -0.0171(15) 0.0123(12) C4 0.0741(14) 0.0394(11) 0.0600(12) -0.0010(9) -0.0024(11) 0.0136(10) C14 0.0596(12) 0.0411(10) 0.0708(14) -0.0022(10) -0.0074(10) -0.0084(9) C23 0.0673(14) 0.0748(15) 0.0387(10) -0.0107(10) -0.0016(9) -0.0134(12) C12 0.0456(10) 0.0576(13) 0.0629(13) 0.0163(10) -0.0015(9) 0.0003(9) C13 0.0542(12) 0.0424(11) 0.0835(16) 0.0140(11) -0.0041(11) -0.0046(9) O2 0.174(3) 0.0511(12) 0.209(4) 0.0240(17) -0.085(3) -0.0229(16) O9 0.145(2) 0.130(2) 0.0890(17) -0.0168(16) -0.0426(17) 0.047(2) C22 0.0672(14) 0.0625(13) 0.0500(12) -0.0139(10) -0.0026(10) -0.0032(11) C33 0.0797(17) 0.0774(17) 0.0713(16) 0.0296(14) 0.0013(13) 0.0050(14) C18 0.0489(12) 0.0534(13) 0.0958(18) -0.0148(12) -0.0051(12) 0.0135(10) C28 0.123(2) 0.087(2) 0.0429(12) -0.0078(12) -0.0006(13) -0.0450(19) O10 0.162(3) 0.163(3) 0.141(3) 0.057(2) -0.083(3) -0.042(3) C24 0.0790(19) 0.120(3) 0.0667(16) -0.0201(17) -0.0115(14) 0.0154(18) C19 0.0578(16) 0.092(2) 0.140(3) -0.029(2) 0.0204(18) 0.0039(15) C20 0.093(2) 0.0696(19) 0.137(3) 0.018(2) -0.018(2) 0.0251(17) C21 0.0774(19) 0.0747(19) 0.151(3) -0.054(2) -0.011(2) 0.0237(16) C26 0.094(3) 0.372(12) 0.058(2) -0.008(4) -0.015(2) -0.098(5) C27 0.162(4) 0.199(5) 0.0524(18) -0.013(2) -0.007(2) -0.130(4) C30 0.080(2) 0.133(3) 0.085(2) 0.012(2) -0.0112(17) 0.022(2) C29 0.088(2) 0.127(4) 0.150(4) 0.031(3) -0.009(2) 0.004(2) C25 0.072(2) 0.280(8) 0.073(2) -0.024(3) -0.0087(18) 0.026(3) C31 0.229(8) 0.140(5) 0.229(8) 0.063(5) -0.126(7) -0.064(5) C32 0.314(14) 0.173(8) 0.309(14) 0.086(9) -0.072(12) -0.081(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 C17 O8 C18 121.97(17) C1 O1 H1 109.5 C17 N1 C1 118.26(15) C17 N1 C9 121.26(16) C1 N1 C9 119.92(15) C15 N4 C22 124.76(19) C16 N4 C15 111.48(17) C16 N4 C22 123.70(19) O4 N3 C6 117.4(2) O5 N3 O4 123.1(2) O5 N3 C6 119.36(19) O8 C17 N1 110.00(16) O7 C17 O8 126.37(18) O7 C17 N1 123.61(19) C7 C2 C1 117.88(18) C3 C2 C1 120.14(18) C3 C2 C7 121.96(19) C7 C6 N3 123.0(2) C5 C6 N3 114.93(18) C5 C6 C7 122.1(2) C10 C15 N4 109.94(17) C14 C15 N4 128.9(2) C14 C15 C10 121.1(2) O1 C1 N1 112.50(17) O1 C1 C2 107.97(16) O1 C1 H1A 109.2 N1 C1 C2 108.69(15) N1 C1 H1A 109.2 C2 C1 H1A 109.2 C2 C7 C8 114.57(16) C6 C7 C2 117.31(19) C6 C7 C8 128.09(19) C15 C10 C9 108.42(17) C11 C10 C15 120.76(19) C11 C10 C9 130.82(19) C7 C8 H8A 109.3 C7 C8 H8B 109.3 C7 C8 C9 111.77(16) H8A C8 H8B 107.9 C9 C8 H8A 109.3 C9 C8 H8B 109.3 C6 C5 H5 121.0 C4 C5 C6 118.07(19) C4 C5 H5 121.0 O6 C16 N4 126.7(2) O6 C16 C9 126.17(19) N4 C16 C9 107.08(16) N1 C9 C10 115.31(15) N1 C9 C8 109.91(15) N1 C9 C16 112.53(16) C10 C9 C8 109.26(16) C10 C9 C16 102.23(15) C16 C9 C8 107.08(15) C2 C3 H3 121.1 C2 C3 C4 117.9(2) C4 C3 H3 121.1 C10 C11 H11 120.3 C10 C11 C12 119.5(2) C12 C11 H11 120.3 O3 N2 C4 118.5(3) O3 N2 O2 123.0(3) O2 N2 C4 118.5(2) C5 C4 C3 122.7(2) C5 C4 N2 118.5(2) C3 C4 N2 118.7(2) C15 C14 H14 121.3 C15 C14 C13 117.4(2) C13 C14 H14 121.3 C28 C23 C22 120.2(3) C24 C23 C22 119.9(3) C24 C23 C28 119.8(3) C11 C12 C33 120.2(2) C13 C12 C11 118.5(2) C13 C12 C33 121.3(2) C14 C13 H13 118.6 C12 C13 C14 122.8(2) C12 C13 H13 118.6 N4 C22 C23 111.9(2) N4 C22 H22A 109.2 N4 C22 H22B 109.2 C23 C22 H22A 109.2 C23 C22 H22B 109.2 H22A C22 H22B 107.9 C12 C33 H33A 109.5 C12 C33 H33B 109.5 C12 C33 H33C 109.5 H33A C33 H33B 109.5 H33A C33 H33C 109.5 H33B C33 H33C 109.5 O8 C18 C19 111.6(2) O8 C18 C20 107.1(2) O8 C18 C21 101.9(2) C19 C18 C20 112.5(3) C19 C18 C21 111.1(3) C21 C18 C20 112.0(3) C23 C28 H28 120.4 C27 C28 C23 119.2(5) C27 C28 H28 120.4 C30 O10 C31 115.8(4) C23 C24 H24 120.8 C23 C24 C25 118.5(4) C25 C24 H24 120.8 C18 C19 H19A 109.5 C18 C19 H19B 109.5 C18 C19 H19C 109.5 H19A C19 H19B 109.5 H19A C19 H19C 109.5 H19B C19 H19C 109.5 C18 C20 H20A 109.5 C18 C20 H20B 109.5 C18 C20 H20C 109.5 H20A C20 H20B 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 C18 C21 H21A 109.5 C18 C21 H21B 109.5 C18 C21 H21C 109.5 H21A C21 H21B 109.5 H21A C21 H21C 109.5 H21B C21 H21C 109.5 C27 C26 H26 120.5 C27 C26 C25 119.1(4) C25 C26 H26 120.5 C28 C27 H27 119.2 C26 C27 C28 121.5(5) C26 C27 H27 119.2 O9 C30 O10 121.9(5) O9 C30 C29 124.7(4) O10 C30 C29 113.2(4) C30 C29 H29A 109.5 C30 C29 H29B 109.5 C30 C29 H29C 109.5 H29A C29 H29B 109.5 H29A C29 H29C 109.5 H29B C29 H29C 109.5 C24 C25 H25 119.0 C26 C25 C24 121.9(6) C26 C25 H25 119.0 O10 C31 H31A 109.1 O10 C31 H31B 109.1 H31A C31 H31B 107.9 C32 C31 O10 112.4(6) C32 C31 H31A 109.1 C32 C31 H31B 109.1 C31 C32 H32A 109.5 C31 C32 H32B 109.5 C31 C32 H32C 109.5 H32A C32 H32B 109.5 H32A C32 H32C 109.5 H32B C32 H32C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O8 C17 1.333(2) O8 C18 1.478(3) O1 H1 0.8200 O1 C1 1.409(3) O6 C16 1.205(3) O7 C17 1.206(2) N1 C17 1.371(3) N1 C1 1.453(2) N1 C9 1.466(2) O4 N3 1.215(3) N4 C15 1.403(3) N4 C16 1.369(3) N4 C22 1.460(3) N3 O5 1.197(3) N3 C6 1.473(3) C2 C1 1.509(3) C2 C7 1.396(3) C2 C3 1.381(3) C6 C7 1.392(3) C6 C5 1.385(3) C15 C10 1.390(3) C15 C14 1.378(3) C1 H1A 0.9800 C7 C8 1.505(3) O3 N2 1.200(3) C10 C9 1.508(3) C10 C11 1.371(3) C8 H8A 0.9700 C8 H8B 0.9700 C8 C9 1.549(3) C5 H5 0.9300 C5 C4 1.366(4) C16 C9 1.549(3) C3 H3 0.9300 C3 C4 1.385(3) C11 H11 0.9300 C11 C12 1.399(3) N2 C4 1.474(3) N2 O2 1.202(4) C14 H14 0.9300 C14 C13 1.385(4) C23 C22 1.500(3) C23 C28 1.389(4) C23 C24 1.374(5) C12 C13 1.384(4) C12 C33 1.499(3) C13 H13 0.9300 O9 C30 1.199(5) C22 H22A 0.9700 C22 H22B 0.9700 C33 H33A 0.9600 C33 H33B 0.9600 C33 H33C 0.9600 C18 C19 1.498(4) C18 C20 1.516(5) C18 C21 1.514(4) C28 H28 0.9300 C28 C27 1.385(6) O10 C30 1.293(5) O10 C31 1.493(7) C24 H24 0.9300 C24 C25 1.392(6) C19 H19A 0.9600 C19 H19B 0.9600 C19 H19C 0.9600 C20 H20A 0.9600 C20 H20B 0.9600 C20 H20C 0.9600 C21 H21A 0.9600 C21 H21B 0.9600 C21 H21C 0.9600 C26 H26 0.9300 C26 C27 1.345(10) C26 C25 1.358(10) C27 H27 0.9300 C30 C29 1.452(7) C29 H29A 0.9600 C29 H29B 0.9600 C29 H29C 0.9600 C25 H25 0.9300 C31 H31A 0.9700 C31 H31B 0.9700 C31 C32 1.339(10) C32 H32A 0.9600 C32 H32B 0.9600 C32 H32C 0.9600