#------------------------------------------------------------------------------ #$Date: 2023-11-01 02:46:34 +0200 (Wed, 01 Nov 2023) $ #$Revision: 287186 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247606.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_7247606 loop_ _publ_author_name 'Li, Chaoyang' 'Niu, Xin-Yue' 'Xu, Wan' 'Bu, Zhanwei' 'Zhang, Wenjing' 'Wang, Qi-Lin' _publ_section_title ; Distinct Reactivities of Ortho-Chalcone-Substituted Organophosphines with Activated Alkynes: Skeletal Editing or Periphery Modification ; _journal_name_full 'Green Chemistry' _journal_paper_doi 10.1039/D3GC03165A _journal_year 2023 _chemical_formula_moiety 'C30 H23 Cl N O2 P' _chemical_formula_sum 'C30 H23 Cl N O2 P' _chemical_formula_weight 495.91 _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 geom _atom_sites_solution_primary dual _audit_creation_date 2022-04-25 _audit_creation_method ; Olex2 1.5-beta (compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439) ; _audit_update_record ; 2023-04-03 deposited with the CCDC. 2023-10-30 downloaded from the CCDC. ; _cell_angle_alpha 89.918(4) _cell_angle_beta 88.573(4) _cell_angle_gamma 81.090(4) _cell_formula_units_Z 2 _cell_length_a 9.7322(16) _cell_length_b 10.0029(16) _cell_length_c 12.561(2) _cell_measurement_reflns_used 3945 _cell_measurement_temperature 296.15 _cell_measurement_theta_max 20.23 _cell_measurement_theta_min 2.62 _cell_volume 1207.7(3) _computing_cell_refinement 'SAINT V8.40B (?, 2016)' _computing_data_reduction 'SAINT V8.40B (?, 2016)' _computing_molecular_graphics 'Olex2 1.5-beta (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5-beta (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2017/1 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 296.15 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1030 _diffrn_reflns_av_unetI/netI 0.0924 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 25964 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.074 _diffrn_reflns_theta_max 25.074 _diffrn_reflns_theta_min 2.061 _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 0.254 _exptl_absorpt_correction_T_max 0.7393 _exptl_absorpt_correction_T_min 0.6908 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0842 before and 0.0767 after correction. The Ratio of minimum to maximum transmission is 0.9344. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.364 _exptl_crystal_description block _exptl_crystal_F_000 516 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.235 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.059 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 316 _refine_ls_number_reflns 4274 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.040 _refine_ls_R_factor_all 0.1320 _refine_ls_R_factor_gt 0.0581 _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^)+(0.0259P)^2^+0.8579P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0897 _refine_ls_wR_factor_ref 0.1155 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2464 _reflns_number_total 4274 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3gc03165a2.cif _cod_data_source_block 43_2 _cod_database_code 7247606 _shelx_shelxl_version_number 2017/1 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.973 _shelx_estimated_absorpt_t_min 0.965 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2.a Ternary CH refined with riding coordinates: C22(H22) 2.b Secondary CH2 refined with riding coordinates: C23(H23A,H23B) 2.c Aromatic/amide H refined with riding coordinates: C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C26(H26), C27(H27), C29(H29), C30(H30) ; _shelx_res_file ; TITL 43_2_a.res in P-1 43_2.res created by SHELXL-2017/1 at 16:19:33 on 25-Apr-2022 REM Old TITL 43_2 in P-1 REM SHELXT solution in P-1 REM R1 0.190, Rweak 0.037, Alpha 0.054, Orientation as input REM Formula found by SHELXT: C30 N O2 P2 CELL 0.71073 9.7322 10.0029 12.5609 89.918 88.573 81.09 ZERR 2 0.0016 0.0016 0.002 0.004 0.004 0.004 LATT 1 SFAC C H Cl N O P UNIT 60 46 2 2 4 2 L.S. 20 0 0 PLAN 9 SIZE 0.11 0.12 0.14 TEMP 23 CONF BOND $H list 4 fmap 2 53 MORE -1 ACTA OMIT 0 0 1 REM REM REM WGHT 0.025900 0.857900 FVAR 0.78960 CL1 3 0.828920 0.595222 0.983324 11.00000 0.05021 0.07418 = 0.07347 -0.01025 -0.00899 -0.00292 P1 6 0.198981 0.764005 0.585109 11.00000 0.03547 0.03128 = 0.03323 -0.00176 -0.00111 -0.00735 O1 5 0.186777 0.935526 1.020962 11.00000 0.06774 0.08655 = 0.04783 -0.02454 -0.00636 0.00954 O2 5 0.325219 1.023939 0.784977 11.00000 0.09320 0.06194 = 0.04954 -0.01356 -0.00422 -0.04175 N1 4 0.217621 0.855115 0.716015 11.00000 0.03483 0.03459 = 0.03081 -0.00260 0.00004 -0.01040 C1 1 0.011977 0.800364 0.622124 11.00000 0.03294 0.02546 = 0.03813 -0.00020 -0.00556 -0.00253 C2 1 -0.019797 0.840946 0.726755 11.00000 0.03473 0.02519 = 0.03818 0.00172 -0.00101 -0.00093 C3 1 -0.154263 0.854867 0.767398 11.00000 0.04175 0.04322 = 0.03546 0.00100 0.00272 -0.00154 AFIX 43 H3 2 -0.173558 0.879953 0.838111 11.00000 -1.20000 AFIX 0 C4 1 -0.259827 0.831180 0.702029 11.00000 0.03191 0.04867 = 0.05977 0.00456 0.00319 -0.00297 AFIX 43 H4 2 -0.350788 0.840758 0.728798 11.00000 -1.20000 AFIX 0 C5 1 -0.231363 0.793378 0.597215 11.00000 0.03436 0.05237 = 0.05163 0.00047 -0.01302 -0.00733 AFIX 43 H5 2 -0.303348 0.779006 0.553406 11.00000 -1.20000 AFIX 0 C6 1 -0.096548 0.776834 0.557194 11.00000 0.03865 0.04287 = 0.03939 -0.00451 -0.00198 -0.00650 AFIX 43 H6 2 -0.077724 0.749945 0.486808 11.00000 -1.20000 AFIX 0 C7 1 0.270836 0.597873 0.634749 11.00000 0.03166 0.03404 = 0.02873 -0.00214 -0.00091 -0.00634 C8 1 0.412416 0.551024 0.629431 11.00000 0.04102 0.03900 = 0.05103 0.00130 0.00488 -0.00798 AFIX 43 H8 2 0.472841 0.606646 0.601992 11.00000 -1.20000 AFIX 0 C9 1 0.464849 0.423046 0.664284 11.00000 0.03686 0.04951 = 0.06280 -0.00320 -0.00058 0.00419 AFIX 43 H9 2 0.560393 0.394029 0.661485 11.00000 -1.20000 AFIX 0 C10 1 0.377989 0.338070 0.702990 11.00000 0.05593 0.03784 = 0.05424 0.00581 -0.00181 0.00333 AFIX 43 H10 2 0.413871 0.251222 0.725234 11.00000 -1.20000 AFIX 0 C11 1 0.237693 0.382466 0.708558 11.00000 0.05345 0.04203 = 0.06827 0.01598 0.00355 -0.01580 AFIX 43 H11 2 0.177819 0.325615 0.734898 11.00000 -1.20000 AFIX 0 C12 1 0.184512 0.511953 0.675051 11.00000 0.03666 0.04151 = 0.06186 0.00630 0.00015 -0.00544 AFIX 43 H12 2 0.089098 0.541300 0.679843 11.00000 -1.20000 AFIX 0 C13 1 0.171284 0.715360 0.442947 11.00000 0.03432 0.03426 = 0.03682 -0.00279 0.00220 -0.00451 C14 1 0.172524 0.583875 0.406437 11.00000 0.03817 0.03927 = 0.03536 0.00163 -0.00277 -0.00717 AFIX 43 H14 2 0.183559 0.512601 0.454653 11.00000 -1.20000 AFIX 0 C15 1 0.157577 0.557354 0.299340 11.00000 0.04715 0.03946 = 0.04516 -0.01240 -0.00073 -0.00924 AFIX 43 H15 2 0.158961 0.468787 0.276404 11.00000 -1.20000 AFIX 0 C16 1 0.140820 0.660882 0.227379 11.00000 0.05667 0.05820 = 0.03155 -0.01101 -0.00165 -0.00157 AFIX 43 H16 2 0.132791 0.642557 0.155429 11.00000 -1.20000 AFIX 0 C17 1 0.135866 0.791663 0.261350 11.00000 0.07730 0.04590 = 0.03517 0.00110 -0.00480 0.00456 AFIX 43 H17 2 0.121633 0.862537 0.212886 11.00000 -1.20000 AFIX 0 C18 1 0.152044 0.817765 0.367542 11.00000 0.07051 0.03312 = 0.03853 -0.00423 -0.00119 -0.00100 AFIX 43 H18 2 0.150019 0.906831 0.389457 11.00000 -1.20000 AFIX 0 C19 1 0.343235 0.852985 0.541906 11.00000 0.04608 0.04526 = 0.03611 0.00332 0.00399 -0.01472 AFIX 43 H19 2 0.382738 0.842182 0.473679 11.00000 -1.20000 AFIX 0 C20 1 0.386937 0.931758 0.611910 11.00000 0.04777 0.04334 = 0.04720 0.00662 0.00005 -0.02119 AFIX 43 H20 2 0.461937 0.977199 0.598313 11.00000 -1.20000 AFIX 0 C21 1 0.308383 0.943380 0.714392 11.00000 0.04830 0.03939 = 0.03892 0.00429 -0.00625 -0.01423 C22 1 0.101527 0.872411 0.790959 11.00000 0.04136 0.03274 = 0.03330 -0.00447 -0.00083 -0.00381 AFIX 13 H22 2 0.082478 0.967769 0.812427 11.00000 -1.20000 AFIX 0 C23 1 0.125815 0.785270 0.891929 11.00000 0.04208 0.05849 = 0.03530 0.00358 0.00136 -0.00738 AFIX 23 H23A 2 0.038006 0.785411 0.930231 11.00000 -1.20000 H23B 2 0.161940 0.692652 0.871848 11.00000 -1.20000 AFIX 0 C24 1 0.227574 0.838935 0.963756 11.00000 0.05686 0.06106 = 0.02585 -0.00100 -0.00107 -0.00956 C25 1 0.376068 0.776376 0.963867 11.00000 0.04806 0.04395 = 0.02883 -0.00025 -0.00289 -0.00688 C26 1 0.466839 0.833519 1.026695 11.00000 0.06186 0.04415 = 0.04404 -0.01002 -0.00789 -0.00022 AFIX 43 H26 2 0.432897 0.910097 1.066865 11.00000 -1.20000 AFIX 0 C27 1 0.605376 0.780381 1.031360 11.00000 0.05776 0.05417 = 0.04884 -0.00883 -0.01471 -0.01357 AFIX 43 H27 2 0.664925 0.821104 1.073051 11.00000 -1.20000 AFIX 0 C28 1 0.654153 0.666228 0.973412 11.00000 0.04217 0.04780 = 0.04074 0.00011 -0.00556 -0.00576 C29 1 0.569156 0.606819 0.909509 11.00000 0.05292 0.05738 = 0.04767 -0.01967 -0.00117 -0.00747 AFIX 43 H29 2 0.604196 0.530107 0.869845 11.00000 -1.20000 AFIX 0 C30 1 0.430541 0.662443 0.904767 11.00000 0.04930 0.05798 = 0.04256 -0.00945 -0.00945 -0.01362 AFIX 43 H30 2 0.372402 0.622757 0.861053 11.00000 -1.20000 AFIX 0 HKLF 4 REM 43_2_a.res in P-1 REM R1 = 0.0581 for 2464 Fo > 4sig(Fo) and 0.1320 for all 4274 data REM 316 parameters refined using 0 restraints END WGHT 0.0297 0.6994 REM Highest difference peak 0.235, deepest hole -0.309, 1-sigma level 0.059 Q1 1 0.2023 0.3773 0.2579 11.00000 0.05 0.24 Q2 1 0.0438 0.5388 0.6113 11.00000 0.05 0.23 Q3 1 0.5971 0.6063 0.7557 11.00000 0.05 0.22 Q4 1 0.0444 0.6533 0.1555 11.00000 0.05 0.22 Q5 1 0.1154 0.9414 0.8190 11.00000 0.05 0.21 Q6 1 -0.2681 0.7387 0.7977 11.00000 0.05 0.21 Q7 1 0.4165 1.0684 0.6218 11.00000 0.05 0.21 Q8 1 0.1226 0.4622 0.4796 11.00000 0.05 0.21 Q9 1 0.0489 0.2933 0.7358 11.00000 0.05 0.21 ; _shelx_res_checksum 69825 _olex2_submission_special_instructions 'No special instructions were received' 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 0.82892(10) 0.59522(11) 0.98332(9) 0.0665(3) Uani 1 1 d . . . . . P1 P 0.19898(9) 0.76400(9) 0.58511(7) 0.0331(2) Uani 1 1 d . . . . . O1 O 0.1868(3) 0.9355(3) 1.0210(2) 0.0695(8) Uani 1 1 d . . . . . O2 O 0.3252(3) 1.0239(3) 0.7850(2) 0.0650(8) Uani 1 1 d . . . . . N1 N 0.2176(3) 0.8551(3) 0.71602(19) 0.0329(7) Uani 1 1 d . . . . . C1 C 0.0120(3) 0.8004(3) 0.6221(3) 0.0323(8) Uani 1 1 d . . . . . C2 C -0.0198(3) 0.8409(3) 0.7268(3) 0.0331(8) Uani 1 1 d . . . . . C3 C -0.1543(4) 0.8549(3) 0.7674(3) 0.0407(9) Uani 1 1 d . . . . . H3 H -0.173558 0.879953 0.838111 0.049 Uiso 1 1 calc R U . . . C4 C -0.2598(4) 0.8312(3) 0.7020(3) 0.0472(10) Uani 1 1 d . . . . . H4 H -0.350788 0.840758 0.728798 0.057 Uiso 1 1 calc R U . . . C5 C -0.2314(4) 0.7934(3) 0.5972(3) 0.0459(9) Uani 1 1 d . . . . . H5 H -0.303348 0.779006 0.553406 0.055 Uiso 1 1 calc R U . . . C6 C -0.0965(4) 0.7768(3) 0.5572(3) 0.0403(9) Uani 1 1 d . . . . . H6 H -0.077724 0.749945 0.486808 0.048 Uiso 1 1 calc R U . . . C7 C 0.2708(3) 0.5979(3) 0.6347(2) 0.0313(8) Uani 1 1 d . . . . . C8 C 0.4124(4) 0.5510(4) 0.6294(3) 0.0436(9) Uani 1 1 d . . . . . H8 H 0.472841 0.606646 0.601992 0.052 Uiso 1 1 calc R U . . . C9 C 0.4648(4) 0.4230(4) 0.6643(3) 0.0509(10) Uani 1 1 d . . . . . H9 H 0.560393 0.394029 0.661485 0.061 Uiso 1 1 calc R U . . . C10 C 0.3780(4) 0.3381(4) 0.7030(3) 0.0505(10) Uani 1 1 d . . . . . H10 H 0.413871 0.251222 0.725234 0.061 Uiso 1 1 calc R U . . . C11 C 0.2377(4) 0.3825(4) 0.7086(3) 0.0538(11) Uani 1 1 d . . . . . H11 H 0.177819 0.325615 0.734898 0.065 Uiso 1 1 calc R U . . . C12 C 0.1845(4) 0.5120(3) 0.6751(3) 0.0468(10) Uani 1 1 d . . . . . H12 H 0.089098 0.541300 0.679843 0.056 Uiso 1 1 calc R U . . . C13 C 0.1713(3) 0.7154(3) 0.4429(3) 0.0353(8) Uani 1 1 d . . . . . C14 C 0.1725(3) 0.5839(3) 0.4064(3) 0.0374(9) Uani 1 1 d . . . . . H14 H 0.183559 0.512601 0.454653 0.045 Uiso 1 1 calc R U . . . C15 C 0.1576(3) 0.5574(4) 0.2993(3) 0.0437(9) Uani 1 1 d . . . . . H15 H 0.158961 0.468787 0.276404 0.052 Uiso 1 1 calc R U . . . C16 C 0.1408(4) 0.6609(4) 0.2274(3) 0.0496(10) Uani 1 1 d . . . . . H16 H 0.132791 0.642557 0.155429 0.059 Uiso 1 1 calc R U . . . C17 C 0.1359(4) 0.7917(4) 0.2613(3) 0.0542(11) Uani 1 1 d . . . . . H17 H 0.121633 0.862537 0.212886 0.065 Uiso 1 1 calc R U . . . C18 C 0.1520(4) 0.8178(4) 0.3675(3) 0.0481(10) Uani 1 1 d . . . . . H18 H 0.150019 0.906831 0.389457 0.058 Uiso 1 1 calc R U . . . C19 C 0.3432(3) 0.8530(3) 0.5419(3) 0.0418(9) Uani 1 1 d . . . . . H19 H 0.382738 0.842182 0.473679 0.050 Uiso 1 1 calc R U . . . C20 C 0.3869(4) 0.9318(3) 0.6119(3) 0.0446(9) Uani 1 1 d . . . . . H20 H 0.461937 0.977199 0.598313 0.054 Uiso 1 1 calc R U . . . C21 C 0.3084(4) 0.9434(4) 0.7144(3) 0.0413(9) Uani 1 1 d . . . . . C22 C 0.1015(3) 0.8724(3) 0.7910(2) 0.0360(8) Uani 1 1 d . . . . . H22 H 0.082478 0.967769 0.812427 0.043 Uiso 1 1 calc R U . . . C23 C 0.1258(4) 0.7853(4) 0.8919(3) 0.0454(9) Uani 1 1 d . . . . . H23A H 0.038006 0.785411 0.930231 0.054 Uiso 1 1 calc R U . . . H23B H 0.161940 0.692652 0.871848 0.054 Uiso 1 1 calc R U . . . C24 C 0.2276(4) 0.8389(4) 0.9638(3) 0.0479(10) Uani 1 1 d . . . . . C25 C 0.3761(4) 0.7764(4) 0.9639(3) 0.0403(9) Uani 1 1 d . . . . . C26 C 0.4668(4) 0.8335(4) 1.0267(3) 0.0507(10) Uani 1 1 d . . . . . H26 H 0.432897 0.910097 1.066865 0.061 Uiso 1 1 calc R U . . . C27 C 0.6054(4) 0.7804(4) 1.0314(3) 0.0528(10) Uani 1 1 d . . . . . H27 H 0.664925 0.821104 1.073051 0.063 Uiso 1 1 calc R U . . . C28 C 0.6542(4) 0.6662(4) 0.9734(3) 0.0436(9) Uani 1 1 d . . . . . C29 C 0.5692(4) 0.6068(4) 0.9095(3) 0.0527(10) Uani 1 1 d . . . . . H29 H 0.604196 0.530107 0.869845 0.063 Uiso 1 1 calc R U . . . C30 C 0.4305(4) 0.6624(4) 0.9048(3) 0.0492(10) Uani 1 1 d . . . . . H30 H 0.372402 0.622757 0.861053 0.059 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 Cl1 0.0502(6) 0.0742(8) 0.0735(8) -0.0102(6) -0.0090(5) -0.0029(5) P1 0.0355(5) 0.0313(5) 0.0332(5) -0.0018(4) -0.0011(4) -0.0073(4) O1 0.068(2) 0.087(2) 0.0478(17) -0.0245(16) -0.0064(14) 0.0095(16) O2 0.093(2) 0.0619(18) 0.0495(17) -0.0136(15) -0.0042(15) -0.0418(16) N1 0.0348(16) 0.0346(16) 0.0308(16) -0.0026(13) 0.0000(13) -0.0104(14) C1 0.033(2) 0.0255(19) 0.038(2) -0.0002(15) -0.0056(17) -0.0025(15) C2 0.035(2) 0.0252(19) 0.038(2) 0.0017(16) -0.0010(17) -0.0009(15) C3 0.042(2) 0.043(2) 0.035(2) 0.0010(17) 0.0027(18) -0.0015(18) C4 0.032(2) 0.049(2) 0.060(3) 0.005(2) 0.003(2) -0.0030(18) C5 0.034(2) 0.052(2) 0.052(3) 0.0005(19) -0.0130(19) -0.0073(18) C6 0.039(2) 0.043(2) 0.039(2) -0.0045(17) -0.0020(18) -0.0065(17) C7 0.032(2) 0.034(2) 0.0287(19) -0.0021(15) -0.0009(15) -0.0063(17) C8 0.041(2) 0.039(2) 0.051(2) 0.0013(18) 0.0049(18) -0.0080(18) C9 0.037(2) 0.050(3) 0.063(3) -0.003(2) -0.001(2) 0.004(2) C10 0.056(3) 0.038(2) 0.054(3) 0.0058(19) -0.002(2) 0.003(2) C11 0.053(3) 0.042(2) 0.068(3) 0.016(2) 0.004(2) -0.016(2) C12 0.037(2) 0.042(2) 0.062(3) 0.006(2) 0.0001(19) -0.0054(19) C13 0.034(2) 0.034(2) 0.037(2) -0.0028(17) 0.0022(16) -0.0045(16) C14 0.038(2) 0.039(2) 0.035(2) 0.0016(17) -0.0028(17) -0.0072(17) C15 0.047(2) 0.039(2) 0.045(2) -0.0124(19) -0.0007(19) -0.0092(18) C16 0.057(3) 0.058(3) 0.032(2) -0.011(2) -0.0016(18) -0.002(2) C17 0.077(3) 0.046(3) 0.035(2) 0.0011(19) -0.005(2) 0.005(2) C18 0.071(3) 0.033(2) 0.039(2) -0.0042(18) -0.001(2) -0.0010(19) C19 0.046(2) 0.045(2) 0.036(2) 0.0033(18) 0.0040(18) -0.0147(19) C20 0.048(2) 0.043(2) 0.047(2) 0.0066(19) 0.0001(19) -0.0212(19) C21 0.048(2) 0.039(2) 0.039(2) 0.0043(18) -0.0062(19) -0.0142(19) C22 0.041(2) 0.033(2) 0.033(2) -0.0045(16) -0.0008(17) -0.0038(16) C23 0.042(2) 0.058(2) 0.035(2) 0.0036(18) 0.0014(18) -0.0074(19) C24 0.057(3) 0.061(3) 0.026(2) -0.0010(19) -0.0011(19) -0.010(2) C25 0.048(2) 0.044(2) 0.029(2) -0.0002(17) -0.0029(18) -0.0069(19) C26 0.062(3) 0.044(2) 0.044(2) -0.0100(19) -0.008(2) 0.000(2) C27 0.058(3) 0.054(3) 0.049(2) -0.009(2) -0.015(2) -0.014(2) C28 0.042(2) 0.048(2) 0.041(2) 0.0001(19) -0.0056(18) -0.0058(19) C29 0.053(3) 0.057(3) 0.048(2) -0.020(2) -0.001(2) -0.007(2) C30 0.049(3) 0.058(3) 0.043(2) -0.009(2) -0.0095(19) -0.014(2) 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' Cl Cl 0.1484 0.1585 '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' P P 0.1023 0.0942 '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 C1 P1 N1 82.69(13) . . ? C1 P1 C13 95.23(14) . . ? C7 P1 N1 94.67(13) . . ? C7 P1 C1 109.14(14) . . ? C7 P1 C13 98.52(14) . . ? C7 P1 C19 108.91(15) . . ? C13 P1 N1 166.58(13) . . ? C19 P1 N1 82.60(14) . . ? C19 P1 C1 140.06(15) . . ? C19 P1 C13 90.76(15) . . ? C21 N1 P1 115.9(2) . . ? C21 N1 C22 120.2(3) . . ? C22 N1 P1 118.3(2) . . ? C2 C1 P1 116.1(2) . . ? C2 C1 C6 118.4(3) . . ? C6 C1 P1 125.2(3) . . ? C1 C2 C22 115.7(3) . . ? C3 C2 C1 121.3(3) . . ? C3 C2 C22 122.9(3) . . ? C2 C3 H3 120.3 . . ? C2 C3 C4 119.3(3) . . ? C4 C3 H3 120.3 . . ? C3 C4 H4 119.8 . . ? C3 C4 C5 120.5(3) . . ? C5 C4 H4 119.8 . . ? C4 C5 H5 119.9 . . ? C6 C5 C4 120.2(3) . . ? C6 C5 H5 119.9 . . ? C1 C6 H6 119.9 . . ? C5 C6 C1 120.2(3) . . ? C5 C6 H6 119.9 . . ? C8 C7 P1 121.5(3) . . ? C12 C7 P1 120.6(3) . . ? C12 C7 C8 117.9(3) . . ? C7 C8 H8 119.6 . . ? C9 C8 C7 120.8(3) . . ? C9 C8 H8 119.6 . . ? C8 C9 H9 119.6 . . ? C10 C9 C8 120.8(3) . . ? C10 C9 H9 119.6 . . ? C9 C10 H10 120.4 . . ? C11 C10 C9 119.2(3) . . ? C11 C10 H10 120.4 . . ? C10 C11 H11 119.9 . . ? C10 C11 C12 120.2(3) . . ? C12 C11 H11 119.9 . . ? C7 C12 C11 121.1(3) . . ? C7 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C14 C13 P1 125.2(3) . . ? C18 C13 P1 117.9(2) . . ? C18 C13 C14 116.8(3) . . ? C13 C14 H14 119.4 . . ? C15 C14 C13 121.1(3) . . ? C15 C14 H14 119.4 . . ? C14 C15 H15 119.9 . . ? C16 C15 C14 120.3(3) . . ? C16 C15 H15 119.9 . . ? C15 C16 H16 120.0 . . ? C15 C16 C17 119.9(3) . . ? C17 C16 H16 120.0 . . ? C16 C17 H17 120.1 . . ? C16 C17 C18 119.7(4) . . ? C18 C17 H17 120.1 . . ? C13 C18 H18 118.9 . . ? C17 C18 C13 122.1(3) . . ? C17 C18 H18 118.9 . . ? P1 C19 H19 121.7 . . ? C20 C19 P1 116.6(3) . . ? C20 C19 H19 121.7 . . ? C19 C20 H20 122.5 . . ? C19 C20 C21 114.9(3) . . ? C21 C20 H20 122.5 . . ? O2 C21 N1 126.9(3) . . ? O2 C21 C20 123.7(3) . . ? N1 C21 C20 109.4(3) . . ? N1 C22 C2 104.2(2) . . ? N1 C22 H22 108.4 . . ? N1 C22 C23 114.0(3) . . ? C2 C22 H22 108.4 . . ? C2 C22 C23 113.2(3) . . ? C23 C22 H22 108.4 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 108.0 . . ? C24 C23 C22 110.9(3) . . ? C24 C23 H23A 109.5 . . ? C24 C23 H23B 109.5 . . ? O1 C24 C23 119.3(4) . . ? O1 C24 C25 119.9(3) . . ? C25 C24 C23 120.9(3) . . ? C26 C25 C24 118.8(3) . . ? C26 C25 C30 117.4(3) . . ? C30 C25 C24 123.8(3) . . ? C25 C26 H26 119.0 . . ? C27 C26 C25 121.9(3) . . ? C27 C26 H26 119.0 . . ? C26 C27 H27 120.6 . . ? C28 C27 C26 118.7(3) . . ? C28 C27 H27 120.6 . . ? C27 C28 Cl1 118.6(3) . . ? C29 C28 Cl1 119.8(3) . . ? C29 C28 C27 121.6(3) . . ? C28 C29 H29 120.5 . . ? C28 C29 C30 119.0(3) . . ? C30 C29 H29 120.5 . . ? C25 C30 H30 119.3 . . ? C29 C30 C25 121.4(3) . . ? C29 C30 H30 119.3 . . ? 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 Cl1 C28 1.746(4) . ? P1 N1 1.907(3) . ? P1 C1 1.848(3) . ? P1 C7 1.816(3) . ? P1 C13 1.888(3) . ? P1 C19 1.845(3) . ? O1 C24 1.215(4) . ? O2 C21 1.230(4) . ? N1 C21 1.342(4) . ? N1 C22 1.442(4) . ? C1 C2 1.389(4) . ? C1 C6 1.399(4) . ? C2 C3 1.380(4) . ? C2 C22 1.519(4) . ? C3 H3 0.9300 . ? C3 C4 1.380(5) . ? C4 H4 0.9300 . ? C4 C5 1.380(5) . ? C5 H5 0.9300 . ? C5 C6 1.379(4) . ? C6 H6 0.9300 . ? C7 C8 1.385(4) . ? C7 C12 1.379(4) . ? C8 H8 0.9300 . ? C8 C9 1.378(5) . ? C9 H9 0.9300 . ? C9 C10 1.369(5) . ? C10 H10 0.9300 . ? C10 C11 1.369(5) . ? C11 H11 0.9300 . ? C11 C12 1.387(5) . ? C12 H12 0.9300 . ? C13 C14 1.392(4) . ? C13 C18 1.389(4) . ? C14 H14 0.9300 . ? C14 C15 1.387(4) . ? C15 H15 0.9300 . ? C15 C16 1.367(5) . ? C16 H16 0.9300 . ? C16 C17 1.370(5) . ? C17 H17 0.9300 . ? C17 C18 1.377(4) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C19 C20 1.304(4) . ? C20 H20 0.9300 . ? C20 C21 1.476(5) . ? C22 H22 0.9800 . ? C22 C23 1.540(4) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C23 C24 1.514(5) . ? C24 C25 1.483(5) . ? C25 C26 1.386(5) . ? C25 C30 1.388(5) . ? C26 H26 0.9300 . ? C26 C27 1.373(5) . ? C27 H27 0.9300 . ? C27 C28 1.370(5) . ? C28 C29 1.367(5) . ? C29 H29 0.9300 . ? C29 C30 1.380(5) . ? C30 H30 0.9300 . ? 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 Cl1 C28 C29 C30 178.4(3) . . . . ? P1 N1 C21 O2 170.9(3) . . . . ? P1 N1 C21 C20 -8.2(4) . . . . ? P1 N1 C22 C2 -14.3(3) . . . . ? P1 N1 C22 C23 109.6(3) . . . . ? P1 C1 C2 C3 -172.0(2) . . . . ? P1 C1 C2 C22 9.8(4) . . . . ? P1 C1 C6 C5 172.6(3) . . . . ? P1 C7 C8 C9 -177.9(3) . . . . ? P1 C7 C12 C11 176.9(3) . . . . ? P1 C13 C14 C15 -177.0(2) . . . . ? P1 C13 C18 C17 177.7(3) . . . . ? P1 C19 C20 C21 -3.1(4) . . . . ? O1 C24 C25 C26 -2.6(5) . . . . ? O1 C24 C25 C30 177.1(4) . . . . ? N1 P1 C1 C2 -14.0(2) . . . . ? N1 P1 C1 C6 172.9(3) . . . . ? N1 P1 C7 C8 -88.4(3) . . . . ? N1 P1 C7 C12 94.3(3) . . . . ? N1 P1 C13 C14 -175.5(5) . . . . ? N1 P1 C13 C18 6.4(7) . . . . ? N1 P1 C19 C20 -1.1(3) . . . . ? N1 C22 C23 C24 72.4(4) . . . . ? C1 P1 C7 C8 -172.3(3) . . . . ? C1 P1 C7 C12 10.5(3) . . . . ? C1 P1 C13 C14 -95.1(3) . . . . ? C1 P1 C13 C18 86.8(3) . . . . ? C1 P1 C19 C20 68.1(4) . . . . ? C1 C2 C3 C4 -1.6(5) . . . . ? C1 C2 C22 N1 2.8(4) . . . . ? C1 C2 C22 C23 -121.6(3) . . . . ? C2 C1 C6 C5 -0.3(5) . . . . ? C2 C3 C4 C5 0.3(5) . . . . ? C2 C22 C23 C24 -168.7(3) . . . . ? C3 C2 C22 N1 -175.4(3) . . . . ? C3 C2 C22 C23 60.2(4) . . . . ? C3 C4 C5 C6 1.0(5) . . . . ? C4 C5 C6 C1 -1.0(5) . . . . ? C6 C1 C2 C3 1.6(5) . . . . ? C6 C1 C2 C22 -176.7(3) . . . . ? C7 P1 C1 C2 78.4(3) . . . . ? C7 P1 C1 C6 -94.6(3) . . . . ? C7 P1 C13 C14 15.2(3) . . . . ? C7 P1 C13 C18 -162.9(3) . . . . ? C7 P1 C19 C20 -93.5(3) . . . . ? C7 C8 C9 C10 1.4(5) . . . . ? C8 C7 C12 C11 -0.4(5) . . . . ? C8 C9 C10 C11 -1.1(6) . . . . ? C9 C10 C11 C12 0.2(6) . . . . ? C10 C11 C12 C7 0.6(6) . . . . ? C12 C7 C8 C9 -0.6(5) . . . . ? C13 P1 C1 C2 179.3(2) . . . . ? C13 P1 C1 C6 6.3(3) . . . . ? C13 P1 C7 C8 89.1(3) . . . . ? C13 P1 C7 C12 -88.1(3) . . . . ? C13 P1 C19 C20 167.2(3) . . . . ? C13 C14 C15 C16 -0.2(5) . . . . ? C14 C13 C18 C17 -0.5(5) . . . . ? C14 C15 C16 C17 -1.4(5) . . . . ? C15 C16 C17 C18 2.0(6) . . . . ? C16 C17 C18 C13 -1.1(6) . . . . ? C18 C13 C14 C15 1.1(5) . . . . ? C19 P1 C1 C2 -83.2(3) . . . . ? C19 P1 C1 C6 103.7(3) . . . . ? C19 P1 C7 C8 -4.7(3) . . . . ? C19 P1 C7 C12 178.1(3) . . . . ? C19 P1 C13 C14 124.4(3) . . . . ? C19 P1 C13 C18 -53.6(3) . . . . ? C19 C20 C21 O2 -171.9(3) . . . . ? C19 C20 C21 N1 7.3(4) . . . . ? C21 N1 C22 C2 138.3(3) . . . . ? C21 N1 C22 C23 -97.8(3) . . . . ? C22 N1 C21 O2 17.7(5) . . . . ? C22 N1 C21 C20 -161.5(3) . . . . ? C22 C2 C3 C4 176.5(3) . . . . ? C22 C23 C24 O1 79.8(4) . . . . ? C22 C23 C24 C25 -99.3(4) . . . . ? C23 C24 C25 C26 176.6(3) . . . . ? C23 C24 C25 C30 -3.8(5) . . . . ? C24 C25 C26 C27 179.5(3) . . . . ? C24 C25 C30 C29 -178.7(3) . . . . ? C25 C26 C27 C28 -1.1(6) . . . . ? C26 C25 C30 C29 1.0(5) . . . . ? C26 C27 C28 Cl1 -177.6(3) . . . . ? C26 C27 C28 C29 1.7(6) . . . . ? C27 C28 C29 C30 -1.0(6) . . . . ? C28 C29 C30 C25 -0.4(6) . . . . ? C30 C25 C26 C27 -0.2(5) . . . . ?