#------------------------------------------------------------------------------ #$Date: 2020-05-01 01:42:52 +0300 (Fri, 01 May 2020) $ #$Revision: 251338 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240431.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_7240431 loop_ _publ_author_name 'Shi, Zhi-Ping' 'Ren, Guo-Bin' 'Qi, Ming-Hui' 'Li, Zhong' 'Xu, Xiaoyong' _publ_section_title ; Design, screening, and properties of novel solvates of azoxystrobin based on isomorphism ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D0CE00204F _journal_year 2020 _chemical_formula_sum 'C22.79 H18.58 Cl1.58 N3 O5' _chemical_formula_weight 470.41 _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 _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-04-07 deposited with the CCDC. 2020-04-30 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.138(16) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.408(4) _cell_length_b 7.7207(14) _cell_length_c 24.595(5) _cell_measurement_temperature 200(2) _cell_volume 2326.3(10) _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 200(2) _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.983 _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0750 _diffrn_reflns_av_unetI/netI 0.0644 _diffrn_reflns_Laue_measured_fraction_full 0.983 _diffrn_reflns_Laue_measured_fraction_max 0.983 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 14008 _diffrn_reflns_point_group_measured_fraction_full 0.983 _diffrn_reflns_point_group_measured_fraction_max 0.983 _diffrn_reflns_theta_full 59.093 _diffrn_reflns_theta_max 59.093 _diffrn_reflns_theta_min 3.640 _exptl_absorpt_coefficient_mu 2.399 _exptl_crystal_density_diffrn 1.343 _exptl_crystal_F_000 973 _exptl_crystal_size_max 0.440 _exptl_crystal_size_mid 0.080 _exptl_crystal_size_min 0.030 _refine_diff_density_max 0.982 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.069 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 328 _refine_ls_number_reflns 3296 _refine_ls_number_restraints 88 _refine_ls_restrained_S_all 1.118 _refine_ls_R_factor_all 0.1181 _refine_ls_R_factor_gt 0.0880 _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^)+(0.0529P)^2^+7.8828P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1869 _refine_ls_wR_factor_ref 0.2045 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2377 _reflns_number_total 3296 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00204f2.cif _cod_data_source_block SC214_MJZ_5_16_0m_a _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7240431 _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 0.418 _shelx_estimated_absorpt_t_max 0.932 _shelx_res_file ; TITL SC214_MJZ_5_16_0m_a.res in P2(1)/n SC214_MJZ_5_16_0m_a.res created by SHELXL-2018/3 at 15:18:04 on 18-Mar-2020 REM Old TITL SC214_MJZ_5_16_0m in P2/n REM SHELXT solution in P2(1)/n REM R1 0.205, Rweak 0.035, Alpha 0.053, Orientation as input REM Formula found by SHELXT: C23 N4 O6 CELL 1.54178 12.4083 7.7207 24.5952 90.000 99.138 90.000 ZERR 4.000 0.0036 0.0014 0.0054 0.000 0.016 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H CL N O UNIT 91.157 74.314 6.314 12 20 TEMP -73.450 SIZE 0.03 0.08 0.44 L.S. 10 BOND $H LIST 4 acta htab conf FMAP 2 PLAN 10 sadi c33 cl1 c33 cl2 sadi c33a cl1a c33a cl2a dfix 1.79 c33 cl1 dfix 1.79 c33 cl2 isor 0.001 cl1 cl1a simu 0.01 c33 > cl2a delu 0.01 c33 > cl2a WGHT 0.052900 7.882800 FVAR 0.45622 0.42150 PART -1 10.500 C33 1 0.092611 0.593306 0.570178 10.50000 0.08421 0.08935 = 0.08911 0.01861 0.03175 -0.01796 AFIX 23 H33A 2 0.103368 0.684964 0.543406 10.50000 -1.20000 H33B 2 0.122560 0.483653 0.557989 10.50000 -1.20000 AFIX 0 CL1 3 -0.045141 0.569115 0.572634 10.50000 0.08892 0.08764 = 0.08525 0.00422 0.01638 0.00205 CL2 3 0.161321 0.649421 0.635934 10.50000 0.11951 0.14150 = 0.09679 0.01958 0.00772 -0.06868 PART 2 -20.500 C33A 1 0.068044 0.598685 0.583340 -20.50000 0.08985 0.09154 = 0.09151 0.02034 0.01799 -0.02270 AFIX 23 H33C 2 0.080907 0.669545 0.551441 -20.50000 -1.20000 H33D 2 0.118754 0.499112 0.585118 -20.50000 -1.20000 AFIX 0 CL1A 3 -0.053981 0.519621 0.567622 -20.50000 0.06686 0.06867 = 0.06562 0.00096 0.01208 -0.00144 CL2A 3 0.108511 0.714778 0.637805 -20.50000 0.13111 0.09047 = 0.11651 0.00706 -0.00551 -0.01759 PART 0 O1 5 0.387214 0.138019 0.517444 11.00000 0.04225 0.02691 = 0.03354 -0.00311 -0.00403 0.00137 N1 4 0.124084 0.122049 0.555279 11.00000 0.06948 0.10954 = 0.06589 -0.01105 0.03421 0.00253 C1 1 0.163018 0.089092 0.517117 11.00000 0.04044 0.06017 = 0.05323 -0.00841 0.00685 -0.00788 O2 5 0.509120 0.620838 0.630058 11.00000 0.03562 0.02867 = 0.03314 -0.00216 -0.00255 0.00537 N2 4 0.328489 0.417737 0.492071 11.00000 0.04195 0.02936 = 0.03362 -0.00064 0.00305 0.00204 C2 1 0.212227 0.047142 0.469420 11.00000 0.04047 0.03364 = 0.03855 -0.00581 0.00779 -0.00161 C3 1 0.149739 -0.019661 0.421998 11.00000 0.03370 0.04237 = 0.05819 -0.00647 0.00108 -0.00211 AFIX 43 H3 2 0.073772 -0.038277 0.421009 11.00000 -1.20000 AFIX 0 O3 5 0.469166 0.663659 0.765849 11.00000 0.03082 0.04486 = 0.06112 -0.02154 0.01205 0.00242 N3 4 0.392140 0.656166 0.551365 11.00000 0.03695 0.03063 = 0.03612 0.00174 0.00131 0.00492 O4 5 0.309468 0.526082 0.755657 11.00000 0.03598 0.05114 = 0.07906 -0.02250 0.02548 -0.00655 C4 1 0.196480 -0.058440 0.377132 11.00000 0.04303 0.04517 = 0.04074 -0.01477 -0.00527 -0.00438 AFIX 43 H4 2 0.153256 -0.104382 0.345026 11.00000 -1.20000 AFIX 0 C5 1 0.308232 -0.030735 0.378206 11.00000 0.04873 0.04333 = 0.03656 -0.00820 0.00482 0.01069 AFIX 43 H5 2 0.341132 -0.058847 0.346997 11.00000 -1.20000 AFIX 0 O5 5 0.447037 0.122203 0.679615 11.00000 0.04640 0.02940 = 0.05828 -0.00760 0.01931 -0.00195 C6 1 0.370258 0.037284 0.424557 11.00000 0.03172 0.02836 = 0.03918 0.00347 0.00367 0.00026 AFIX 43 H6 2 0.446213 0.055736 0.425445 11.00000 -1.20000 AFIX 0 C7 1 0.322737 0.078515 0.469477 11.00000 0.03491 0.02221 = 0.03264 -0.00077 0.00111 0.00321 C8 1 0.389180 0.313701 0.527544 11.00000 0.02861 0.02349 = 0.03210 -0.00028 0.00622 0.00221 C9 1 0.455293 0.368636 0.574457 11.00000 0.03122 0.02513 = 0.03632 0.00197 0.00243 0.00764 AFIX 43 H9 2 0.499824 0.291191 0.598246 11.00000 -1.20000 AFIX 0 C10 1 0.452596 0.543022 0.584596 11.00000 0.02272 0.03516 = 0.02738 -0.00320 0.00142 0.00173 C11 1 0.334756 0.585092 0.506567 11.00000 0.04086 0.03290 = 0.03437 0.00769 -0.00356 0.00307 AFIX 43 H11 2 0.292965 0.662951 0.481741 11.00000 -1.20000 AFIX 0 C12 1 0.593138 0.527139 0.662479 11.00000 0.03073 0.02474 = 0.02523 -0.00778 -0.00205 0.00204 C13 1 0.696746 0.544914 0.650187 11.00000 0.03317 0.03041 = 0.03497 -0.00279 0.00510 -0.00106 AFIX 43 H13 2 0.709042 0.610904 0.619152 11.00000 -1.20000 AFIX 0 C14 1 0.783698 0.464949 0.683801 11.00000 0.03418 0.04512 = 0.04401 -0.01013 0.00755 0.00278 AFIX 43 H14 2 0.855832 0.476388 0.675866 11.00000 -1.20000 AFIX 0 C15 1 0.764343 0.368686 0.728851 11.00000 0.02941 0.04306 = 0.04236 -0.00322 -0.00150 0.01302 AFIX 43 H15 2 0.823151 0.313959 0.751969 11.00000 -1.20000 AFIX 0 C16 1 0.659754 0.352877 0.739873 11.00000 0.04862 0.03933 = 0.02503 -0.00071 0.00731 0.00303 AFIX 43 H16 2 0.647630 0.287325 0.771026 11.00000 -1.20000 AFIX 0 C17 1 0.570715 0.429623 0.706962 11.00000 0.02878 0.02521 = 0.03140 -0.00375 0.00054 0.00126 C18 1 0.457638 0.401624 0.718188 11.00000 0.02930 0.03250 = 0.03065 -0.00002 0.00467 0.00457 C19 1 0.403111 0.532586 0.747544 11.00000 0.03187 0.03293 = 0.04030 -0.00587 0.00430 -0.00019 C20 1 0.422854 0.794134 0.798074 11.00000 0.04595 0.06145 = 0.08971 -0.04711 0.01626 -0.00050 AFIX 137 H20A 2 0.472021 0.894090 0.803841 11.00000 -1.50000 H20B 2 0.413609 0.745087 0.833794 11.00000 -1.50000 H20C 2 0.351744 0.831088 0.778287 11.00000 -1.50000 AFIX 0 C21 1 0.403106 0.254193 0.704495 11.00000 0.03537 0.03308 = 0.03953 -0.00271 0.01397 0.00435 AFIX 43 H21 2 0.331114 0.242301 0.712587 11.00000 -1.20000 AFIX 0 C22 1 0.372505 -0.014832 0.657690 11.00000 0.06556 0.03408 = 0.06768 -0.01024 0.02707 -0.01058 AFIX 137 H22A 2 0.344898 0.008266 0.618791 11.00000 -1.50000 H22B 2 0.311249 -0.019229 0.678371 11.00000 -1.50000 H22C 2 0.411050 -0.126052 0.661107 11.00000 -1.50000 PART 0 AFIX 0 HKLF 4 REM SC214_MJZ_5_16_0m_a.res in P2(1)/n REM wR2 = 0.204548, GooF = S = 1.11390, Restrained GooF = 1.11819 for all data REM R1 = 0.088034 for 2377 Fo > 4sig(Fo) and 0.118069 for all 3296 data REM 328 parameters refined using 88 restraints END WGHT 0.0529 7.8828 REM Instructions for potential hydrogen bonds HTAB C9 O5 EQIV $1 -x+1/2, y+1/2, -z+3/2 HTAB C20 O4_$1 EQIV $2 -x+1/2, y-1/2, -z+3/2 HTAB C21 O4_$2 HTAB C22 O4_$2 EQIV $3 x, y-1, z HTAB C22 O2_$3 REM Highest difference peak 0.982, deepest hole -0.316, 1-sigma level 0.069 Q1 1 0.0405 0.5504 0.5210 11.00000 0.05 0.98 Q2 1 0.0270 0.6623 0.6082 11.00000 0.05 0.50 Q3 1 0.0206 0.7156 0.6408 11.00000 0.05 0.38 Q4 1 0.1819 0.5019 0.6146 11.00000 0.05 0.23 Q5 1 0.1437 0.7389 0.5989 11.00000 0.05 0.22 Q6 1 0.8536 0.4574 0.7689 11.00000 0.05 0.22 Q7 1 0.1380 0.7137 0.6427 11.00000 0.05 0.21 Q8 1 0.4451 0.0250 0.5053 11.00000 0.05 0.21 Q9 1 0.2693 -0.2741 0.4026 11.00000 0.05 0.21 Q10 1 0.5801 0.5998 0.7466 11.00000 0.05 0.20 ; _shelx_res_checksum 25035 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 C33 C 0.0926(10) 0.593(3) 0.5702(6) 0.086(4) Uani 0.5 1 d D U P A -1 H33A H 0.103368 0.684964 0.543406 0.103 Uiso 0.5 1 calc R U P A -1 H33B H 0.122560 0.483653 0.557989 0.103 Uiso 0.5 1 calc R U P A -1 Cl1 Cl -0.0451(6) 0.5691(9) 0.5726(3) 0.087(2) Uani 0.5 1 d D U P A -1 Cl2 Cl 0.1613(6) 0.6494(11) 0.6359(3) 0.120(3) Uani 0.5 1 d D U P A -1 C33A C 0.068(3) 0.599(6) 0.5833(14) 0.091(4) Uani 0.289(5) 1 d D U P B 2 H33C H 0.080907 0.669545 0.551441 0.109 Uiso 0.289(5) 1 calc R U P B 2 H33D H 0.118754 0.499112 0.585118 0.109 Uiso 0.289(5) 1 calc R U P B 2 Cl1A Cl -0.0540(9) 0.5196(14) 0.5676(5) 0.067(3) Uani 0.289(5) 1 d D U P B 2 Cl2A Cl 0.1085(11) 0.7148(18) 0.6378(7) 0.115(4) Uani 0.289(5) 1 d D U P B 2 O1 O 0.3872(3) 0.1380(4) 0.51744(14) 0.0353(9) Uani 1 1 d . . . . . N1 N 0.1241(5) 0.1220(9) 0.5553(3) 0.079(2) Uani 1 1 d . . . . . C1 C 0.1630(5) 0.0891(9) 0.5171(3) 0.0513(17) Uani 1 1 d . . . . . O2 O 0.5091(3) 0.6208(4) 0.63006(14) 0.0333(9) Uani 1 1 d . . . . . N2 N 0.3285(4) 0.4177(6) 0.49207(18) 0.0353(11) Uani 1 1 d . . . . . C2 C 0.2122(4) 0.0471(7) 0.4694(2) 0.0374(14) Uani 1 1 d . . . . . C3 C 0.1497(5) -0.0197(8) 0.4220(3) 0.0454(15) Uani 1 1 d . . . . . H3 H 0.073772 -0.038277 0.421009 0.055 Uiso 1 1 calc R U . . . O3 O 0.4692(3) 0.6637(5) 0.76585(16) 0.0451(11) Uani 1 1 d . . . . . N3 N 0.3921(3) 0.6562(6) 0.55136(18) 0.0351(11) Uani 1 1 d . . . . . O4 O 0.3095(3) 0.5261(5) 0.75566(18) 0.0536(12) Uani 1 1 d . . . . . C4 C 0.1965(5) -0.0584(8) 0.3771(2) 0.0443(15) Uani 1 1 d . . . . . H4 H 0.153256 -0.104382 0.345026 0.053 Uiso 1 1 calc R U . . . C5 C 0.3082(5) -0.0307(8) 0.3782(2) 0.0431(15) Uani 1 1 d . . . . . H5 H 0.341132 -0.058847 0.346997 0.052 Uiso 1 1 calc R U . . . O5 O 0.4470(3) 0.1222(5) 0.67962(16) 0.0435(10) Uani 1 1 d . . . . . C6 C 0.3703(4) 0.0373(7) 0.4246(2) 0.0333(13) Uani 1 1 d . . . . . H6 H 0.446213 0.055736 0.425445 0.040 Uiso 1 1 calc R U . . . C7 C 0.3227(4) 0.0785(6) 0.4695(2) 0.0304(12) Uani 1 1 d . . . . . C8 C 0.3892(4) 0.3137(6) 0.5275(2) 0.0279(12) Uani 1 1 d . . . . . C9 C 0.4553(4) 0.3686(7) 0.5745(2) 0.0312(12) Uani 1 1 d . . . . . H9 H 0.499824 0.291191 0.598246 0.037 Uiso 1 1 calc R U . . . C10 C 0.4526(4) 0.5430(7) 0.5846(2) 0.0287(12) Uani 1 1 d . . . . . C11 C 0.3348(4) 0.5851(7) 0.5066(2) 0.0371(13) Uani 1 1 d . . . . . H11 H 0.292965 0.662951 0.481741 0.044 Uiso 1 1 calc R U . . . C12 C 0.5931(4) 0.5271(7) 0.6625(2) 0.0276(12) Uani 1 1 d . . . . . C13 C 0.6967(4) 0.5449(7) 0.6502(2) 0.0329(13) Uani 1 1 d . . . . . H13 H 0.709042 0.610904 0.619152 0.039 Uiso 1 1 calc R U . . . C14 C 0.7837(4) 0.4649(8) 0.6838(2) 0.0410(14) Uani 1 1 d . . . . . H14 H 0.855832 0.476388 0.675866 0.049 Uiso 1 1 calc R U . . . C15 C 0.7643(4) 0.3687(7) 0.7289(2) 0.0391(14) Uani 1 1 d . . . . . H15 H 0.823151 0.313959 0.751969 0.047 Uiso 1 1 calc R U . . . C16 C 0.6598(4) 0.3529(7) 0.7399(2) 0.0375(14) Uani 1 1 d . . . . . H16 H 0.647630 0.287325 0.771026 0.045 Uiso 1 1 calc R U . . . C17 C 0.5707(4) 0.4296(7) 0.7070(2) 0.0289(12) Uani 1 1 d . . . . . C18 C 0.4576(4) 0.4016(7) 0.7182(2) 0.0308(12) Uani 1 1 d . . . . . C19 C 0.4031(4) 0.5326(7) 0.7475(2) 0.0352(13) Uani 1 1 d . . . . . C20 C 0.4229(5) 0.7941(9) 0.7981(3) 0.065(2) Uani 1 1 d . . . . . H20A H 0.472021 0.894090 0.803841 0.098 Uiso 1 1 calc R U . . . H20B H 0.413609 0.745087 0.833794 0.098 Uiso 1 1 calc R U . . . H20C H 0.351744 0.831088 0.778287 0.098 Uiso 1 1 calc R U . . . C21 C 0.4031(4) 0.2542(7) 0.7045(2) 0.0351(13) Uani 1 1 d . . . . . H21 H 0.331114 0.242301 0.712587 0.042 Uiso 1 1 calc R U . . . C22 C 0.3725(5) -0.0148(8) 0.6577(3) 0.0540(17) Uani 1 1 d . . . . . H22A H 0.344898 0.008266 0.618791 0.081 Uiso 1 1 calc R U . . . H22B H 0.311249 -0.019229 0.678371 0.081 Uiso 1 1 calc R U . . . H22C H 0.411050 -0.126052 0.661107 0.081 Uiso 1 1 calc R U . . . 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 C33 0.084(6) 0.089(7) 0.089(7) 0.019(7) 0.032(6) -0.018(7) Cl1 0.089(3) 0.088(3) 0.085(3) 0.0042(19) 0.0164(16) 0.0020(19) Cl2 0.120(5) 0.141(7) 0.097(4) 0.020(5) 0.008(4) -0.069(5) C33A 0.090(7) 0.092(8) 0.092(8) 0.020(7) 0.018(8) -0.023(7) Cl1A 0.067(3) 0.069(3) 0.066(3) 0.0010(19) 0.0121(18) -0.0014(19) Cl2A 0.131(9) 0.090(7) 0.117(7) 0.007(6) -0.006(7) -0.018(6) O1 0.042(2) 0.027(2) 0.034(2) -0.0031(16) -0.0040(17) 0.0014(17) N1 0.069(4) 0.110(6) 0.066(4) -0.011(4) 0.034(3) 0.003(4) C1 0.040(3) 0.060(4) 0.053(4) -0.008(3) 0.007(3) -0.008(3) O2 0.0356(19) 0.029(2) 0.033(2) -0.0022(17) -0.0025(16) 0.0054(17) N2 0.042(3) 0.029(3) 0.034(3) -0.001(2) 0.003(2) 0.002(2) C2 0.040(3) 0.034(3) 0.039(3) -0.006(3) 0.008(3) -0.002(3) C3 0.034(3) 0.042(4) 0.058(4) -0.006(3) 0.001(3) -0.002(3) O3 0.031(2) 0.045(2) 0.061(3) -0.022(2) 0.0120(19) 0.0024(19) N3 0.037(2) 0.031(3) 0.036(3) 0.002(2) 0.001(2) 0.005(2) O4 0.036(2) 0.051(3) 0.079(3) -0.022(2) 0.025(2) -0.007(2) C4 0.043(3) 0.045(4) 0.041(3) -0.015(3) -0.005(3) -0.004(3) C5 0.049(4) 0.043(4) 0.037(3) -0.008(3) 0.005(3) 0.011(3) O5 0.046(2) 0.029(2) 0.058(3) -0.0076(19) 0.0193(19) -0.0020(19) C6 0.032(3) 0.028(3) 0.039(3) 0.003(3) 0.004(3) 0.000(2) C7 0.035(3) 0.022(3) 0.033(3) -0.001(2) 0.001(2) 0.003(2) C8 0.029(3) 0.023(3) 0.032(3) 0.000(2) 0.006(2) 0.002(2) C9 0.031(3) 0.025(3) 0.036(3) 0.002(2) 0.002(2) 0.008(2) C10 0.023(3) 0.035(3) 0.027(3) -0.003(2) 0.001(2) 0.002(2) C11 0.041(3) 0.033(3) 0.034(3) 0.008(3) -0.004(3) 0.003(3) C12 0.031(3) 0.025(3) 0.025(3) -0.008(2) -0.002(2) 0.002(2) C13 0.033(3) 0.030(3) 0.035(3) -0.003(2) 0.005(2) -0.001(2) C14 0.034(3) 0.045(4) 0.044(4) -0.010(3) 0.008(3) 0.003(3) C15 0.029(3) 0.043(4) 0.042(3) -0.003(3) -0.002(3) 0.013(3) C16 0.049(3) 0.039(3) 0.025(3) -0.001(3) 0.007(3) 0.003(3) C17 0.029(3) 0.025(3) 0.031(3) -0.004(2) 0.001(2) 0.001(2) C18 0.029(3) 0.033(3) 0.031(3) 0.000(2) 0.005(2) 0.005(3) C19 0.032(3) 0.033(3) 0.040(3) -0.006(3) 0.004(3) 0.000(3) C20 0.046(4) 0.061(5) 0.090(5) -0.047(4) 0.016(4) 0.000(3) C21 0.035(3) 0.033(3) 0.040(3) -0.003(3) 0.014(3) 0.004(3) C22 0.066(4) 0.034(4) 0.068(4) -0.010(3) 0.027(4) -0.011(3) 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' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl1 C33 Cl2 109.4(9) . . ? Cl1 C33 H33A 109.8 . . ? Cl2 C33 H33A 109.8 . . ? Cl1 C33 H33B 109.8 . . ? Cl2 C33 H33B 109.8 . . ? H33A C33 H33B 108.2 . . ? Cl1A C33A Cl2A 124(2) . . ? Cl1A C33A H33C 106.3 . . ? Cl2A C33A H33C 106.3 . . ? Cl1A C33A H33D 106.3 . . ? Cl2A C33A H33D 106.3 . . ? H33C C33A H33D 106.4 . . ? C8 O1 C7 117.9(4) . . ? N1 C1 C2 179.7(8) . . ? C10 O2 C12 118.5(4) . . ? C8 N2 C11 113.9(5) . . ? C7 C2 C3 118.8(5) . . ? C7 C2 C1 120.3(5) . . ? C3 C2 C1 120.8(5) . . ? C4 C3 C2 120.6(5) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C19 O3 C20 115.7(4) . . ? C11 N3 C10 114.2(5) . . ? C3 C4 C5 120.0(5) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 119.8(5) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C21 O5 C22 116.1(4) . . ? C7 C6 C5 120.1(5) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C2 120.6(5) . . ? C6 C7 O1 119.8(5) . . ? C2 C7 O1 119.4(4) . . ? N2 C8 C9 124.5(5) . . ? N2 C8 O1 119.0(4) . . ? C9 C8 O1 116.5(4) . . ? C10 C9 C8 115.3(5) . . ? C10 C9 H9 122.3 . . ? C8 C9 H9 122.3 . . ? N3 C10 O2 112.2(5) . . ? N3 C10 C9 123.8(5) . . ? O2 C10 C9 124.0(5) . . ? N3 C11 N2 128.2(5) . . ? N3 C11 H11 115.9 . . ? N2 C11 H11 115.9 . . ? C13 C12 C17 122.5(5) . . ? C13 C12 O2 117.3(5) . . ? C17 C12 O2 120.0(4) . . ? C12 C13 C14 119.2(5) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C15 C14 C13 119.7(5) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C16 C15 C14 119.6(5) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 122.3(5) . . ? C15 C16 H16 118.8 . . ? C17 C16 H16 118.8 . . ? C12 C17 C16 116.6(5) . . ? C12 C17 C18 122.4(5) . . ? C16 C17 C18 120.9(5) . . ? C21 C18 C19 117.1(5) . . ? C21 C18 C17 122.0(5) . . ? C19 C18 C17 120.8(5) . . ? O4 C19 O3 122.0(5) . . ? O4 C19 C18 125.6(5) . . ? O3 C19 C18 112.4(4) . . ? O3 C20 H20A 109.5 . . ? O3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 O5 122.1(5) . . ? C18 C21 H21 118.9 . . ? O5 C21 H21 118.9 . . ? O5 C22 H22A 109.5 . . ? O5 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O5 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C33 Cl1 1.730(12) . ? C33 Cl2 1.758(12) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C33A Cl1A 1.62(2) . ? C33A Cl2A 1.62(2) . ? C33A H33C 0.9900 . ? C33A H33D 0.9900 . ? O1 C8 1.378(6) . ? O1 C7 1.394(6) . ? N1 C1 1.150(8) . ? C1 C2 1.443(8) . ? O2 C10 1.362(6) . ? O2 C12 1.408(6) . ? N2 C8 1.328(6) . ? N2 C11 1.339(7) . ? C2 C7 1.392(7) . ? C2 C3 1.393(8) . ? C3 C4 1.359(8) . ? C3 H3 0.9500 . ? O3 C19 1.335(6) . ? O3 C20 1.455(6) . ? N3 C11 1.332(7) . ? N3 C10 1.341(6) . ? O4 C19 1.211(6) . ? C4 C5 1.399(8) . ? C4 H4 0.9500 . ? C5 C6 1.374(7) . ? C5 H5 0.9500 . ? O5 C21 1.348(6) . ? O5 C22 1.452(7) . ? C6 C7 1.370(7) . ? C6 H6 0.9500 . ? C8 C9 1.372(7) . ? C9 C10 1.371(7) . ? C9 H9 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.373(7) . ? C12 C17 1.392(7) . ? C13 C14 1.395(8) . ? C13 H13 0.9500 . ? C14 C15 1.386(8) . ? C14 H14 0.9500 . ? C15 C16 1.373(7) . ? C15 H15 0.9500 . ? C16 C17 1.394(7) . ? C16 H16 0.9500 . ? C17 C18 1.488(7) . ? C18 C21 1.340(7) . ? C18 C19 1.469(7) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21 0.9500 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? 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 C7 C2 C3 C4 2.0(9) . . . . ? C1 C2 C3 C4 179.8(6) . . . . ? C2 C3 C4 C5 -0.3(9) . . . . ? C3 C4 C5 C6 -0.6(9) . . . . ? C4 C5 C6 C7 -0.3(9) . . . . ? C5 C6 C7 C2 2.0(8) . . . . ? C5 C6 C7 O1 176.3(5) . . . . ? C3 C2 C7 C6 -2.9(8) . . . . ? C1 C2 C7 C6 179.3(5) . . . . ? C3 C2 C7 O1 -177.1(5) . . . . ? C1 C2 C7 O1 5.0(8) . . . . ? C8 O1 C7 C6 100.8(6) . . . . ? C8 O1 C7 C2 -84.8(6) . . . . ? C11 N2 C8 C9 -1.5(7) . . . . ? C11 N2 C8 O1 178.6(4) . . . . ? C7 O1 C8 N2 1.3(7) . . . . ? C7 O1 C8 C9 -178.6(4) . . . . ? N2 C8 C9 C10 2.5(8) . . . . ? O1 C8 C9 C10 -177.6(4) . . . . ? C11 N3 C10 O2 -179.5(4) . . . . ? C11 N3 C10 C9 -0.7(7) . . . . ? C12 O2 C10 N3 -166.6(4) . . . . ? C12 O2 C10 C9 14.6(7) . . . . ? C8 C9 C10 N3 -1.2(7) . . . . ? C8 C9 C10 O2 177.4(4) . . . . ? C10 N3 C11 N2 1.9(8) . . . . ? C8 N2 C11 N3 -0.8(8) . . . . ? C10 O2 C12 C13 91.7(6) . . . . ? C10 O2 C12 C17 -92.0(5) . . . . ? C17 C12 C13 C14 -1.0(8) . . . . ? O2 C12 C13 C14 175.2(5) . . . . ? C12 C13 C14 C15 0.2(8) . . . . ? C13 C14 C15 C16 0.1(9) . . . . ? C14 C15 C16 C17 0.5(9) . . . . ? C13 C12 C17 C16 1.5(8) . . . . ? O2 C12 C17 C16 -174.6(4) . . . . ? C13 C12 C17 C18 -176.1(5) . . . . ? O2 C12 C17 C18 7.7(7) . . . . ? C15 C16 C17 C12 -1.3(8) . . . . ? C15 C16 C17 C18 176.5(5) . . . . ? C12 C17 C18 C21 100.8(6) . . . . ? C16 C17 C18 C21 -76.8(7) . . . . ? C12 C17 C18 C19 -82.4(7) . . . . ? C16 C17 C18 C19 100.0(6) . . . . ? C20 O3 C19 O4 2.5(8) . . . . ? C20 O3 C19 C18 -176.7(5) . . . . ? C21 C18 C19 O4 -7.7(9) . . . . ? C17 C18 C19 O4 175.3(5) . . . . ? C21 C18 C19 O3 171.5(5) . . . . ? C17 C18 C19 O3 -5.5(7) . . . . ? C19 C18 C21 O5 -177.1(5) . . . . ? C17 C18 C21 O5 -0.1(8) . . . . ? C22 O5 C21 C18 -168.5(5) . . . . ?