#------------------------------------------------------------------------------ #$Date: 2019-12-13 03:37:30 +0200 (Fri, 13 Dec 2019) $ #$Revision: 245032 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125648.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_7125648 loop_ _publ_author_name 'Lei, Jian' 'Gao, Huaxin' 'Huang, Miaoling' 'Liu, Xiao' 'Mao, Yangfang' 'Xie, Xiaolan' _publ_section_title ; Copper-Catalyzed Stereoselective Alkylhydrazination of Alkynes ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/C9CC07998J _journal_year 2019 _chemical_formula_sum 'C21 H29 Cl N2 O6' _chemical_formula_weight 440.91 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2019-10-09 deposited with the CCDC. 2019-12-11 downloaded from the CCDC. ; _cell_angle_alpha 63.811(8) _cell_angle_beta 72.144(8) _cell_angle_gamma 69.542(8) _cell_formula_units_Z 2 _cell_length_a 10.3139(9) _cell_length_b 11.3380(10) _cell_length_c 12.3840(10) _cell_measurement_reflns_used 1819 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 21.8970 _cell_measurement_theta_min 3.6050 _cell_volume 1197.4(2) _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXL-2018/3 (Sheldrick, 2018)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_unetI/netI 0.0580 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 8370 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.017 _diffrn_reflns_theta_max 25.017 _diffrn_reflns_theta_min 3.331 _diffrn_source 'fine-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 0.196 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.76036 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour white _exptl_crystal_density_diffrn 1.223 _exptl_crystal_description block _exptl_crystal_F_000 468 _exptl_crystal_size_max 0.120 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.110 _refine_diff_density_max 0.149 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.035 _refine_ls_extinction_coef 0.078(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 321 _refine_ls_number_reflns 4219 _refine_ls_number_restraints 948 _refine_ls_restrained_S_all 0.996 _refine_ls_R_factor_all 0.0953 _refine_ls_R_factor_gt 0.0528 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0527P)^2^+0.1809P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1144 _refine_ls_wR_factor_ref 0.1395 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2561 _reflns_number_total 4219 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc07998j2.cif _cod_data_source_block exp_7324 _cod_database_code 7125648 _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. ; _shelx_estimated_absorpt_t_min 0.977 _shelx_estimated_absorpt_t_max 0.979 _shelx_res_file ; TITL CF solution in P-1 exp_7324.res created by SHELXL-2018/3 at 20:21:56 on 09-Oct-2019 CELL 0.71073 10.313927 11.338018 12.384007 63.811 72.1435 69.5422 ZERR 2 0.000918 0.000976 0.001044 0.0084 0.0078 0.0081 LATT 1 SFAC C H N O Cl UNIT 42 58 4 12 2 OMIT -3.00 50.04 L.S. 10 ACTA BOND FMAP 2 PLAN 10 size 0.12 0.11 0.12 simu 0.02 0.04 3.8 WGHT 0.052700 0.180900 EXTI 0.078343 FVAR 10.07745 0.62115 0.62502 CL1 5 0.398953 -0.154331 0.216010 11.00000 0.14289 0.05895 = 0.10101 -0.02759 0.00074 -0.03170 N1 3 0.291085 0.494439 0.143437 11.00000 0.04825 0.05132 = 0.03677 -0.00137 -0.00946 -0.02406 N2 3 0.291609 0.596810 0.028982 11.00000 0.06170 0.04846 = 0.03641 -0.00345 -0.00580 -0.01963 AFIX 43 H2A 2 0.333040 0.578840 -0.035730 11.00000 -1.20000 AFIX 0 O1 4 -0.161367 0.267009 0.431057 11.00000 0.11022 0.08608 = 0.07379 -0.00806 -0.00081 -0.06165 O2 4 -0.086916 0.416580 0.449409 11.00000 0.09789 0.09587 = 0.04643 -0.01354 -0.00630 -0.05220 O3 4 0.375202 0.372550 0.314037 11.00000 0.05212 0.06819 = 0.04510 -0.00298 -0.01349 -0.02694 O4 4 0.501000 0.508511 0.154601 11.00000 0.04917 0.06783 = 0.05811 -0.01554 -0.00140 -0.03058 O5 4 0.248052 0.807630 -0.097861 11.00000 0.09317 0.04900 = 0.08601 0.01207 -0.02554 -0.02507 O6 4 0.156503 0.759996 0.104627 11.00000 0.09743 0.06228 = 0.10335 -0.03615 0.00592 -0.02878 C1 1 0.337227 0.011223 0.211397 11.00000 0.07813 0.05258 = 0.06791 -0.01963 -0.00910 -0.02113 C2 1 0.378586 0.114502 0.107787 11.00000 0.09940 0.06543 = 0.05977 -0.02579 0.01235 -0.02845 AFIX 43 H2 2 0.438866 0.095742 0.040914 11.00000 -1.20000 AFIX 0 C3 1 0.330587 0.245601 0.103304 11.00000 0.07898 0.05513 = 0.04847 -0.01259 0.00168 -0.02656 AFIX 43 H3 2 0.360047 0.314964 0.033411 11.00000 -1.20000 AFIX 0 C4 1 0.239293 0.276232 0.200823 11.00000 0.04805 0.05475 = 0.04179 -0.01067 -0.00674 -0.02248 C5 1 0.201180 0.169466 0.304696 11.00000 0.05815 0.05786 = 0.04568 -0.00938 -0.00242 -0.02077 AFIX 43 H5 2 0.141667 0.187279 0.372245 11.00000 -1.20000 AFIX 0 C6 1 0.249574 0.037153 0.310202 11.00000 0.06650 0.05328 = 0.05795 -0.00467 -0.01236 -0.02314 AFIX 43 H6 2 0.222618 -0.033217 0.380464 11.00000 -1.20000 AFIX 0 C7 1 0.184527 0.418770 0.191512 11.00000 0.04979 0.05205 = 0.03441 -0.00843 -0.00612 -0.02360 C8 1 0.052466 0.486384 0.215430 11.00000 0.05132 0.05172 = 0.04217 -0.01122 -0.00739 -0.02166 AFIX 43 H8 2 0.041690 0.573365 0.210720 11.00000 -1.20000 AFIX 0 C9 1 -0.084383 0.445263 0.249309 11.00000 0.04421 0.05991 = 0.05236 -0.01118 -0.01073 -0.02086 C10 1 -0.114879 0.363935 0.385613 11.00000 0.04571 0.06027 = 0.05666 -0.01061 -0.00707 -0.01957 C11 1 -0.087296 0.367450 0.176642 11.00000 0.07215 0.10404 = 0.06956 -0.02815 -0.01541 -0.04542 AFIX 137 H11A 2 -0.065735 0.419245 0.090696 11.00000 -1.50000 H11B 2 -0.179192 0.352454 0.196147 11.00000 -1.50000 H11C 2 -0.018793 0.281659 0.197331 11.00000 -1.50000 AFIX 0 C12 1 -0.203781 0.576902 0.222316 11.00000 0.05610 0.07738 = 0.07982 -0.00048 -0.02263 -0.01752 AFIX 137 H12A 2 -0.207622 0.624552 0.271329 11.00000 -1.50000 H12B 2 -0.291898 0.554570 0.241569 11.00000 -1.50000 H12C 2 -0.186075 0.633445 0.137265 11.00000 -1.50000 AFIX 0 C13 1 -0.111187 0.350347 0.581101 11.00000 0.12179 0.13034 = 0.05085 -0.01691 -0.00622 -0.04449 AFIX 137 H13A 2 -0.209609 0.354479 0.611140 11.00000 -1.50000 H13B 2 -0.081721 0.395384 0.615885 11.00000 -1.50000 H13C 2 -0.058363 0.257156 0.603802 11.00000 -1.50000 AFIX 0 C14 1 0.399264 0.461567 0.200878 11.00000 0.04649 0.04846 = 0.04174 -0.01407 -0.00141 -0.01864 C15 1 0.487354 0.314217 0.385304 11.00000 0.06095 0.07867 = 0.06014 -0.00545 -0.02628 -0.02325 PART 1 AFIX 3 H15 2 0.579332 0.306566 0.331198 21.00000 -1.20000 PART 2 H15A 2 0.550485 0.373715 0.357033 -21.00000 -1.20000 PART 1 AFIX 0 C16 1 0.471818 0.405185 0.446491 21.00000 0.08042 0.13742 = 0.07110 -0.03956 -0.02698 -0.02817 AFIX 137 H16A 2 0.480422 0.492938 0.386064 21.00000 -1.50000 H16B 2 0.543851 0.368199 0.494959 21.00000 -1.50000 H16C 2 0.381042 0.413789 0.498386 21.00000 -1.50000 AFIX 0 C17 1 0.469948 0.176486 0.469629 21.00000 0.13933 0.10398 = 0.11910 0.03537 -0.08413 -0.03989 AFIX 137 H17A 2 0.381575 0.184051 0.524935 21.00000 -1.50000 H17B 2 0.545220 0.129523 0.515369 21.00000 -1.50000 H17C 2 0.471791 0.126798 0.423124 21.00000 -1.50000 PART 2 AFIX 0 C16' 1 0.410832 0.292201 0.520795 -21.00000 0.13566 0.16546 = 0.06299 -0.01978 -0.05120 0.01005 AFIX 137 H16D 2 0.365097 0.378719 0.528094 -21.00000 -1.50000 H16E 2 0.478516 0.242022 0.574186 -21.00000 -1.50000 H16F 2 0.342012 0.242376 0.543092 -21.00000 -1.50000 AFIX 0 C17' 1 0.567898 0.180566 0.374359 -21.00000 0.09457 0.11372 = 0.10912 -0.03480 -0.04562 0.00605 AFIX 137 H17D 2 0.503392 0.128926 0.389195 -21.00000 -1.50000 H17E 2 0.629190 0.131408 0.433357 -21.00000 -1.50000 H17F 2 0.622811 0.195580 0.293500 -21.00000 -1.50000 PART 0 AFIX 0 C18 1 0.225570 0.726260 0.020479 11.00000 0.06325 0.05000 = 0.06834 -0.00716 -0.01212 -0.02650 C19 1 0.165483 0.947998 -0.126808 11.00000 0.11903 0.04872 = 0.14718 0.00988 -0.04923 -0.02386 PART 1 AFIX 3 H19 2 0.072242 0.954546 -0.074507 31.00000 -1.20000 PART 2 H19A 2 0.137392 0.968408 -0.052566 -31.00000 -1.20000 PART 1 AFIX 0 C20 1 0.155165 0.994075 -0.268557 31.00000 0.21180 0.10180 = 0.19028 0.05335 -0.10594 -0.04562 AFIX 137 H20A 2 0.109239 1.089001 -0.300279 31.00000 -1.50000 H20B 2 0.102046 0.942575 -0.273584 31.00000 -1.50000 H20C 2 0.248105 0.977916 -0.315688 31.00000 -1.50000 AFIX 0 C21 1 0.237578 1.027049 -0.114178 31.00000 0.16406 0.06170 = 0.19934 -0.00965 -0.05043 -0.04820 AFIX 137 H21A 2 0.235038 1.002804 -0.028978 31.00000 -1.50000 H21B 2 0.192519 1.121705 -0.149816 31.00000 -1.50000 H21C 2 0.333614 1.009749 -0.155255 31.00000 -1.50000 PART 2 AFIX 0 C20' 1 0.043890 0.964945 -0.165508 -31.00000 0.12278 0.06942 = 0.14816 -0.05052 -0.06231 0.01799 AFIX 137 H20D 2 0.069038 0.929607 -0.228779 -31.00000 -1.50000 H20E 2 -0.002573 1.059775 -0.196674 -31.00000 -1.50000 H20F 2 -0.018210 0.917081 -0.097619 -31.00000 -1.50000 AFIX 0 C21' 1 0.255977 1.038179 -0.216470 -31.00000 0.20065 0.07398 = 0.20435 0.04468 -0.03429 -0.06887 AFIX 137 H21D 2 0.285641 1.021486 -0.290989 -31.00000 -1.50000 H21E 2 0.337041 1.020573 -0.183833 -31.00000 -1.50000 H21F 2 0.204103 1.131127 -0.232899 -31.00000 -1.50000 PART 0 AFIX 0 HKLF 4 REM CF solution in P-1 REM wR2 = 0.1395, GooF = S = 1.017, Restrained GooF = 0.996 for all data REM R1 = 0.0528 for 2561 Fo > 4sig(Fo) and 0.0953 for all 4219 data REM 321 parameters refined using 948 restraints END WGHT 0.0523 0.1818 REM Highest difference peak 0.149, deepest hole -0.192, 1-sigma level 0.035 Q1 1 0.2045 1.0241 -0.0291 11.00000 0.05 0.14 Q2 1 -0.2116 0.3688 0.4177 11.00000 0.05 0.14 Q3 1 0.3404 -0.2612 0.3732 11.00000 0.05 0.14 Q4 1 -0.0065 0.3050 0.6022 11.00000 0.05 0.14 Q5 1 0.3034 -0.1994 0.2820 11.00000 0.05 0.13 Q6 1 0.0860 1.0316 -0.2241 11.00000 0.05 0.13 Q7 1 0.3978 0.2999 0.0445 11.00000 0.05 0.13 Q8 1 0.3439 -0.1749 0.3358 11.00000 0.05 0.13 Q9 1 0.4351 -0.0932 0.0755 11.00000 0.05 0.12 Q10 1 0.2307 0.4557 0.1635 11.00000 0.05 0.12 ; _shelx_res_checksum 62342 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.39895(11) -0.15433(8) 0.21601(9) 0.1057(4) Uani 1 1 d . U . . . N1 N 0.2911(2) 0.4944(2) 0.14344(17) 0.0474(5) Uani 1 1 d . U . . . N2 N 0.2916(2) 0.5968(2) 0.02898(18) 0.0527(6) Uani 1 1 d . U . . . H2A H 0.333040 0.578840 -0.035730 0.063 Uiso 1 1 calc R U . . . O1 O -0.1614(2) 0.2670(2) 0.43106(19) 0.0916(7) Uani 1 1 d . U . . . O2 O -0.0869(2) 0.4166(2) 0.44941(18) 0.0787(6) Uani 1 1 d . U . . . O3 O 0.37520(17) 0.37255(18) 0.31404(15) 0.0575(5) Uani 1 1 d . U . . . O4 O 0.50100(17) 0.50851(18) 0.15460(16) 0.0589(5) Uani 1 1 d . U . . . O5 O 0.2481(2) 0.80763(19) -0.0979(2) 0.0860(7) Uani 1 1 d . U . . . O6 O 0.1565(2) 0.7600(2) 0.1046(2) 0.0892(7) Uani 1 1 d . U . . . C1 C 0.3372(3) 0.0112(3) 0.2114(3) 0.0670(8) Uani 1 1 d . U . . . C2 C 0.3786(3) 0.1145(3) 0.1078(3) 0.0784(9) Uani 1 1 d . U . . . H2 H 0.438866 0.095742 0.040914 0.094 Uiso 1 1 calc R U . . . C3 C 0.3306(3) 0.2456(3) 0.1033(3) 0.0640(8) Uani 1 1 d . U . . . H3 H 0.360047 0.314964 0.033411 0.077 Uiso 1 1 calc R U . . . C4 C 0.2393(2) 0.2762(3) 0.2008(2) 0.0486(6) Uani 1 1 d . U . . . C5 C 0.2012(3) 0.1695(3) 0.3047(2) 0.0577(7) Uani 1 1 d . U . . . H5 H 0.141667 0.187279 0.372245 0.069 Uiso 1 1 calc R U . . . C6 C 0.2496(3) 0.0372(3) 0.3102(3) 0.0628(8) Uani 1 1 d . U . . . H6 H 0.222618 -0.033217 0.380464 0.075 Uiso 1 1 calc R U . . . C7 C 0.1845(3) 0.4188(2) 0.1915(2) 0.0456(6) Uani 1 1 d . U . . . C8 C 0.0525(3) 0.4864(3) 0.2154(2) 0.0486(6) Uani 1 1 d . U . . . H8 H 0.041690 0.573365 0.210720 0.058 Uiso 1 1 calc R U . . . C9 C -0.0844(2) 0.4453(3) 0.2493(2) 0.0532(7) Uani 1 1 d . U . . . C10 C -0.1149(3) 0.3639(3) 0.3856(3) 0.0573(7) Uani 1 1 d . U . . . C11 C -0.0873(3) 0.3674(3) 0.1766(3) 0.0762(9) Uani 1 1 d . U . . . H11A H -0.065735 0.419245 0.090696 0.114 Uiso 1 1 calc R U . . . H11B H -0.179192 0.352454 0.196147 0.114 Uiso 1 1 calc R U . . . H11C H -0.018793 0.281659 0.197331 0.114 Uiso 1 1 calc R U . . . C12 C -0.2038(3) 0.5769(3) 0.2223(3) 0.0794(9) Uani 1 1 d . U . . . H12A H -0.207622 0.624552 0.271329 0.119 Uiso 1 1 calc R U . . . H12B H -0.291898 0.554570 0.241569 0.119 Uiso 1 1 calc R U . . . H12C H -0.186075 0.633445 0.137265 0.119 Uiso 1 1 calc R U . . . C13 C -0.1112(4) 0.3503(4) 0.5811(3) 0.1062(12) Uani 1 1 d . U . . . H13A H -0.209609 0.354479 0.611140 0.159 Uiso 1 1 calc R U . . . H13B H -0.081721 0.395384 0.615885 0.159 Uiso 1 1 calc R U . . . H13C H -0.058363 0.257156 0.603802 0.159 Uiso 1 1 calc R U . . . C14 C 0.3993(3) 0.4616(2) 0.2009(2) 0.0463(6) Uani 1 1 d . U . . . C15 C 0.4874(3) 0.3142(3) 0.3853(3) 0.0690(8) Uani 1 1 d . U . . . H15 H 0.579332 0.306566 0.331198 0.083 Uiso 0.621(7) 1 d R U P A 1 H15A H 0.550485 0.373715 0.357033 0.083 Uiso 0.379(7) 1 d R U P A 2 C16 C 0.4718(6) 0.4052(7) 0.4465(6) 0.093(2) Uani 0.621(7) 1 d . U P A 1 H16A H 0.480422 0.492938 0.386064 0.139 Uiso 0.621(7) 1 calc R U P A 1 H16B H 0.543851 0.368199 0.494959 0.139 Uiso 0.621(7) 1 calc R U P A 1 H16C H 0.381042 0.413789 0.498386 0.139 Uiso 0.621(7) 1 calc R U P A 1 C17 C 0.4699(10) 0.1765(8) 0.4696(8) 0.132(4) Uani 0.621(7) 1 d . U P A 1 H17A H 0.381575 0.184051 0.524935 0.199 Uiso 0.621(7) 1 calc R U P A 1 H17B H 0.545220 0.129523 0.515369 0.199 Uiso 0.621(7) 1 calc R U P A 1 H17C H 0.471791 0.126798 0.423124 0.199 Uiso 0.621(7) 1 calc R U P A 1 C16' C 0.4108(14) 0.2922(17) 0.5208(10) 0.136(5) Uani 0.379(7) 1 d . U P A 2 H16D H 0.365097 0.378719 0.528094 0.204 Uiso 0.379(7) 1 calc R U P A 2 H16E H 0.478516 0.242022 0.574186 0.204 Uiso 0.379(7) 1 calc R U P A 2 H16F H 0.342012 0.242376 0.543092 0.204 Uiso 0.379(7) 1 calc R U P A 2 C17' C 0.5679(13) 0.1806(12) 0.3744(13) 0.111(4) Uani 0.379(7) 1 d . U P A 2 H17D H 0.503392 0.128926 0.389195 0.167 Uiso 0.379(7) 1 calc R U P A 2 H17E H 0.629190 0.131408 0.433357 0.167 Uiso 0.379(7) 1 calc R U P A 2 H17F H 0.622811 0.195580 0.293500 0.167 Uiso 0.379(7) 1 calc R U P A 2 C18 C 0.2256(3) 0.7263(3) 0.0205(3) 0.0627(8) Uani 1 1 d . U . . . C19 C 0.1655(5) 0.9480(3) -0.1268(4) 0.1157(14) Uani 1 1 d . U . . . H19 H 0.072242 0.954546 -0.074507 0.139 Uiso 0.625(9) 1 d R U P B 1 H19A H 0.137392 0.968408 -0.052566 0.139 Uiso 0.375(9) 1 d R U P B 2 C20 C 0.1552(14) 0.9941(8) -0.2686(11) 0.190(5) Uani 0.625(9) 1 d . U P B 1 H20A H 0.109239 1.089001 -0.300279 0.285 Uiso 0.625(9) 1 calc R U P B 1 H20B H 0.102046 0.942575 -0.273584 0.285 Uiso 0.625(9) 1 calc R U P B 1 H20C H 0.248105 0.977916 -0.315688 0.285 Uiso 0.625(9) 1 calc R U P B 1 C21 C 0.2376(10) 1.0270(8) -0.1142(12) 0.147(4) Uani 0.625(9) 1 d . U P B 1 H21A H 0.235038 1.002804 -0.028978 0.220 Uiso 0.625(9) 1 calc R U P B 1 H21B H 0.192519 1.121705 -0.149816 0.220 Uiso 0.625(9) 1 calc R U P B 1 H21C H 0.333614 1.009749 -0.155255 0.220 Uiso 0.625(9) 1 calc R U P B 1 C20' C 0.0439(14) 0.9649(11) -0.1655(14) 0.112(4) Uani 0.375(9) 1 d . U P B 2 H20D H 0.069038 0.929607 -0.228779 0.169 Uiso 0.375(9) 1 calc R U P B 2 H20E H -0.002573 1.059775 -0.196674 0.169 Uiso 0.375(9) 1 calc R U P B 2 H20F H -0.018210 0.917081 -0.097619 0.169 Uiso 0.375(9) 1 calc R U P B 2 C21' C 0.256(2) 1.0382(15) -0.216(2) 0.187(8) Uani 0.375(9) 1 d . U P B 2 H21D H 0.285641 1.021486 -0.290989 0.281 Uiso 0.375(9) 1 calc R U P B 2 H21E H 0.337041 1.020573 -0.183833 0.281 Uiso 0.375(9) 1 calc R U P B 2 H21F H 0.204103 1.131127 -0.232899 0.281 Uiso 0.375(9) 1 calc R U P B 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 Cl1 0.1429(9) 0.0589(5) 0.1010(8) -0.0276(5) 0.0007(6) -0.0317(5) N1 0.0483(12) 0.0513(12) 0.0368(12) -0.0014(10) -0.0095(9) -0.0241(10) N2 0.0617(13) 0.0485(13) 0.0364(12) -0.0034(10) -0.0058(10) -0.0196(11) O1 0.1102(17) 0.0861(15) 0.0738(16) -0.0081(13) -0.0008(13) -0.0617(14) O2 0.0979(15) 0.0959(15) 0.0464(12) -0.0135(11) -0.0063(11) -0.0522(13) O3 0.0521(10) 0.0682(12) 0.0451(11) -0.0030(9) -0.0135(8) -0.0269(9) O4 0.0492(10) 0.0678(12) 0.0581(12) -0.0155(10) -0.0014(9) -0.0306(9) O5 0.0932(15) 0.0490(12) 0.0860(16) 0.0121(11) -0.0255(12) -0.0251(11) O6 0.0974(17) 0.0623(14) 0.1033(19) -0.0361(14) 0.0059(14) -0.0288(12) C1 0.078(2) 0.0526(16) 0.068(2) -0.0196(15) -0.0091(16) -0.0211(15) C2 0.099(2) 0.0654(19) 0.060(2) -0.0258(16) 0.0124(17) -0.0285(18) C3 0.0790(19) 0.0551(17) 0.0485(17) -0.0126(13) 0.0017(14) -0.0266(15) C4 0.0480(14) 0.0548(15) 0.0418(15) -0.0107(12) -0.0067(11) -0.0225(12) C5 0.0582(16) 0.0579(16) 0.0457(16) -0.0094(13) -0.0024(12) -0.0208(13) C6 0.0665(18) 0.0533(17) 0.0580(19) -0.0047(14) -0.0124(15) -0.0231(14) C7 0.0498(15) 0.0521(14) 0.0344(14) -0.0084(11) -0.0061(11) -0.0236(12) C8 0.0513(15) 0.0517(14) 0.0422(15) -0.0112(12) -0.0074(11) -0.0217(12) C9 0.0442(14) 0.0599(16) 0.0524(17) -0.0112(13) -0.0107(12) -0.0209(13) C10 0.0457(15) 0.0603(17) 0.0567(18) -0.0106(15) -0.0071(13) -0.0196(14) C11 0.0721(19) 0.104(2) 0.070(2) -0.0281(18) -0.0154(16) -0.0454(18) C12 0.0561(18) 0.077(2) 0.080(2) -0.0005(17) -0.0226(16) -0.0175(16) C13 0.122(3) 0.130(3) 0.051(2) -0.017(2) -0.006(2) -0.044(3) C14 0.0465(14) 0.0485(14) 0.0417(15) -0.0141(12) -0.0014(12) -0.0186(12) C15 0.0609(18) 0.079(2) 0.0601(19) -0.0054(17) -0.0263(15) -0.0232(16) C16 0.080(4) 0.137(5) 0.071(4) -0.040(4) -0.027(3) -0.028(4) C17 0.139(7) 0.104(5) 0.119(7) 0.035(5) -0.084(6) -0.040(5) C16' 0.136(9) 0.165(11) 0.063(7) -0.020(7) -0.051(6) 0.010(8) C17' 0.095(7) 0.114(8) 0.109(8) -0.035(7) -0.046(6) 0.006(6) C18 0.0632(18) 0.0500(17) 0.068(2) -0.0072(16) -0.0121(15) -0.0265(15) C19 0.119(3) 0.049(2) 0.147(4) 0.010(2) -0.049(3) -0.024(2) C20 0.212(10) 0.102(6) 0.190(10) 0.053(6) -0.106(8) -0.046(6) C21 0.164(7) 0.062(4) 0.199(9) -0.010(6) -0.050(7) -0.048(4) C20' 0.123(9) 0.069(6) 0.148(10) -0.051(6) -0.062(7) 0.018(6) C21' 0.201(11) 0.074(7) 0.204(14) 0.045(10) -0.034(13) -0.069(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 C14 N1 N2 117.57(18) C14 N1 C7 123.08(19) N2 N1 C7 119.07(19) C18 N2 N1 118.7(2) C10 O2 C13 117.9(2) C14 O3 C15 117.53(19) C18 O5 C19 115.2(3) C6 C1 C2 120.7(3) C6 C1 Cl1 119.9(2) C2 C1 Cl1 119.3(2) C1 C2 C3 119.8(3) C2 C3 C4 121.2(3) C3 C4 C5 117.6(2) C3 C4 C7 120.0(2) C5 C4 C7 122.3(2) C6 C5 C4 121.5(3) C1 C6 C5 119.1(3) C8 C7 N1 116.9(2) C8 C7 C4 128.7(2) N1 C7 C4 114.3(2) C7 C8 C9 130.6(2) C10 C9 C8 110.3(2) C10 C9 C11 110.5(2) C8 C9 C11 113.5(2) C10 C9 C12 106.8(2) C8 C9 C12 107.3(2) C11 C9 C12 108.2(2) O1 C10 O2 123.4(3) O1 C10 C9 125.2(3) O2 C10 C9 111.4(2) O4 C14 O3 125.8(2) O4 C14 N1 124.4(2) O3 C14 N1 109.86(19) O3 C15 C16 107.9(3) O3 C15 C17 105.1(3) C16 C15 C17 114.6(5) O3 C15 C17' 107.7(5) O3 C15 C16' 105.4(5) C17' C15 C16' 110.1(8) O6 C18 O5 126.8(3) O6 C18 N2 125.3(3) O5 C18 N2 107.8(3) C20' C19 O5 109.7(5) C21 C19 O5 110.5(5) C20' C19 C21' 114.2(11) O5 C19 C21' 108.7(8) C21 C19 C20 111.4(6) O5 C19 C20 102.0(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C1 1.739(3) N1 C14 1.361(3) N1 N2 1.380(3) N1 C7 1.451(3) N2 C18 1.356(3) O1 C10 1.188(3) O2 C10 1.319(3) O2 C13 1.444(3) O3 C14 1.326(3) O3 C15 1.460(3) O4 C14 1.210(3) O5 C18 1.342(3) O5 C19 1.457(4) O6 C18 1.202(3) C1 C6 1.362(4) C1 C2 1.374(4) C2 C3 1.374(4) C3 C4 1.382(3) C4 C5 1.387(3) C4 C7 1.477(3) C5 C6 1.383(4) C7 C8 1.324(3) C8 C9 1.520(3) C9 C10 1.517(4) C9 C11 1.525(4) C9 C12 1.544(4) C15 C16 1.471(6) C15 C17 1.484(7) C15 C17' 1.496(11) C15 C16' 1.567(12) C19 C20' 1.399(11) C19 C21 1.429(9) C19 C21' 1.476(15) C19 C20 1.622(12)