#------------------------------------------------------------------------------ #$Date: 2020-02-04 22:11:19 +0200 (Tue, 04 Feb 2020) $ #$Revision: 247625 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125625.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_7125625 loop_ _publ_author_name 'Itazaki, Masumi' 'Matsutani, Takanari' 'Nochida, Tomoya' 'Moriuchi, Toshiyuki' 'Nakazawa, Hiroshi' _publ_section_title ; Convenient synthesis of phosphinecarboxamide and phosphinecarbothioamide by hydrophosphination of isocyanates and isothiocyanates. ; _journal_issue 3 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 443 _journal_page_last 445 _journal_paper_doi 10.1039/c9cc08329d _journal_volume 56 _journal_year 2020 _chemical_formula_moiety 'C15 H15 Cl N O P' _chemical_formula_sum 'C15 H15 Cl N O P' _chemical_formula_weight 291.70 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _audit_creation_date 2017-12-04 _audit_creation_method 'generated by ACTA instruction via SHELXL-2014/7' _audit_update_record ; 2019-10-15 deposited with the CCDC. 2019-11-29 downloaded from the CCDC. ; _cell_angle_alpha 85.569(6) _cell_angle_beta 82.125(7) _cell_angle_gamma 67.021(6) _cell_formula_units_Z 4 _cell_length_a 9.29470(10) _cell_length_b 11.8190(2) _cell_length_c 14.4600(6) _cell_measurement_reflns_used 3471 _cell_measurement_temperature 200(2) _cell_measurement_theta_max 27.4855 _cell_measurement_theta_min 2.3217 _cell_volume 1448.16(10) _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_molecular_graphics 'Ortep for Windows (Farrugia, 2012)' _computing_publication_material 'WinGX publication routines (Farrugia, 2012)' _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _computing_structure_solution SIR97 _diffrn_ambient_temperature 200(2) _diffrn_detector_area_resol_mean 7.32 _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_details ; scan: Number of images: 600 Slice: -80.0000 - 100.000 Image width: 0.3000 Exp time: 4.0000 Rotation axis: Phi Omega: 0.0000 Chi: 0.0000 Phi: 0.0000 XTD: 55.2286 2theta: 24.9882 scan: Number of images: 200 Slice: -15.0000 - 45.0000 Image width: 0.3000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Chi: 90.0000 Phi: 0.0000 XTD: 55.2286 2theta: 24.9882 scan: Number of images: 200 Slice: -15.0000 - 45.0000 Image width: 0.3000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Chi: 90.0000 Phi: 90.0000 XTD: 55.2286 2theta: 24.9882 scan: Number of images: 200 Slice: -15.0000 - 45.0000 Image width: 0.3000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Chi: 90.0000 Phi: 180.0000 XTD: 55.2286 2theta: 24.9882 scan: Number of images: 200 Slice: -15.0000 - 45.0000 Image width: 0.3000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Chi: 90.0000 Phi: 270.0000 XTD: 55.2286 2theta: 24.9882 scan: Number of images: 190 Slice: -15.0000 - 42.0000 Image width: 0.3000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 0.0000 XTD: 55.2286 2theta: 24.9882 scan: Number of images: 190 Slice: -15.0000 - 42.0000 Image width: 0.3000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 90.0000 XTD: 55.2286 2theta: 24.9882 scan: Number of images: 190 Slice: -15.0000 - 42.0000 Image width: 0.3000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 180.0000 XTD: 55.2286 2theta: 24.9882 scan: Number of images: 190 Slice: -15.0000 - 42.0000 Image width: 0.3000 Exp time: 4.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 270.0000 XTD: 55.2286 2theta: 24.9882 ; _diffrn_measurement_device 'Mercury CCD (2x2 bin mode)' _diffrn_measurement_device_details 'AFC7: Eulerian 3-circle' _diffrn_measurement_device_type 'Rigaku/MSC Mercury CCD' _diffrn_measurement_method '\w and \f' _diffrn_radiation_detector CCD _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71070 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_unetI/netI 0.0361 _diffrn_reflns_Laue_measured_fraction_full 0.990 _diffrn_reflns_Laue_measured_fraction_max 0.988 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 17154 _diffrn_reflns_point_group_measured_fraction_full 0.990 _diffrn_reflns_point_group_measured_fraction_max 0.988 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.489 _diffrn_reflns_theta_min 2.322 _diffrn_source_current 250.0000 _diffrn_source_power 13.7500 _diffrn_source_voltage 55.0000 _exptl_absorpt_coefficient_mu 0.365 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.7349 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 608 _exptl_crystal_preparation 'mounted on the CryoLoop with Palaton oil and placed in N2 stream at 200(2) K' _exptl_crystal_size_max 0.370 _exptl_crystal_size_mid 0.270 _exptl_crystal_size_min 0.120 _refine_diff_density_max 0.302 _refine_diff_density_min -0.416 _refine_diff_density_rms 0.052 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 463 _refine_ls_number_reflns 6564 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.106 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0478 _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^)+(0.0350P)^2^+1.1505P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1146 _refine_ls_wR_factor_ref 0.1187 _reflns_number_gt 5783 _reflns_number_total 6564 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc08329d2.cif _cod_data_source_block MTK-201 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas Adding full bibliography for 7125625.cif. ; _cod_original_cell_volume 1448.16(9) _cod_database_code 7125625 _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. ; _shelx_estimated_absorpt_t_min 0.877 _shelx_estimated_absorpt_t_max 0.957 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL _2017_32_Process REM Yadorkari-X generated CELL 0.71075 9.2947 11.8190 14.4600 85.5688 82.1250 67.0214 ZERR 4.0 0.0001 0.0002 0.0006 0.0063 0.0065 0.0058 LATT 1 REM SPGR P-1 triclinic SFAC C H N O P Cl UNIT 60 60 4 4 4 4 SIZE 0.37 0.27 0.12 TEMP -72.8 L.S. 10 FMAP 2 PLAN -25 ACTA CONF WPDB -1 BOND$H MERG 2 OMIT -10.000000 55.000000 OMIT 2 3 0 OMIT -7 -5 3 HTAB C1 O2 HTAB N1 O2 EQIV $1 -x+1, -y, -z+1 HTAB C11 Cl2_$1 EQIV $2 x-1, y, z HTAB N2 O1_$2 HTAB LIST 4 WGHT 0.035000 1.150500 FVAR 7.69454 CL1 6 0.863269 -0.140849 0.147981 11.00000 0.08008 0.04715 = 0.06359 0.00104 -0.01340 -0.02615 C1 1 0.822499 0.001826 0.085911 11.00000 0.04037 0.04724 = 0.03131 -0.00561 -0.00835 -0.01384 H1A 2 0.861856 -0.015820 0.019368 11.00000 0.05146 H1B 2 0.708135 0.042465 0.093368 11.00000 0.04967 C2 1 0.893524 0.079680 0.125333 11.00000 0.04124 0.04640 = 0.03483 -0.00593 -0.00350 -0.01750 H2A 2 1.002284 0.030428 0.132729 11.00000 0.05530 H2B 2 0.879438 0.146501 0.087224 11.00000 0.04366 N1 3 0.814010 0.124632 0.216688 11.00000 0.02536 0.04761 = 0.04144 -0.01439 -0.00507 -0.00936 H1N 2 0.718573 0.152185 0.226860 11.00000 0.04419 C3 1 0.889431 0.115472 0.290263 11.00000 0.02610 0.02785 = 0.03849 -0.00317 -0.00516 -0.01298 O1 4 1.033234 0.063843 0.288061 11.00000 0.02257 0.04887 = 0.04719 -0.00696 -0.00493 -0.01139 P1 5 0.764142 0.171066 0.403093 11.00000 0.02811 0.03197 = 0.03339 -0.00173 -0.00275 -0.01335 C4 1 0.900218 0.215820 0.457885 11.00000 0.02834 0.03327 = 0.03398 -0.00719 -0.00531 -0.00845 C5 1 0.964205 0.298563 0.416359 11.00000 0.03395 0.04103 = 0.04379 -0.00632 -0.00724 -0.01535 H5A 2 0.939265 0.338192 0.352635 11.00000 0.05027 C6 1 1.064054 0.330811 0.462095 11.00000 0.03467 0.04528 = 0.06084 -0.01802 -0.00562 -0.01568 H6A 2 1.102095 0.387699 0.435625 11.00000 0.06209 C7 1 1.100238 0.280833 0.549057 11.00000 0.03297 0.05949 = 0.05868 -0.03011 -0.01249 -0.00753 H7A 2 1.161643 0.303380 0.579747 11.00000 0.07527 C8 1 1.038777 0.198240 0.591106 11.00000 0.04466 0.05987 = 0.03955 -0.01353 -0.01612 -0.00104 H8A 2 1.059476 0.159674 0.650159 11.00000 0.05465 C9 1 0.938551 0.164993 0.545432 11.00000 0.03952 0.04064 = 0.03809 -0.00429 -0.00799 -0.00593 H9A 2 0.893556 0.108241 0.573336 11.00000 0.05065 C10 1 0.618125 0.321396 0.370409 11.00000 0.02426 0.03235 = 0.03834 -0.00799 -0.00459 -0.01151 C11 1 0.479686 0.366937 0.431041 11.00000 0.03340 0.04969 = 0.04320 -0.01218 0.00329 -0.01899 H11A 2 0.469838 0.318035 0.484685 11.00000 0.04022 C12 1 0.365357 0.482404 0.414762 11.00000 0.02770 0.05107 = 0.07103 -0.02663 0.00403 -0.00933 H12A 2 0.278827 0.511660 0.459355 11.00000 0.06574 C13 1 0.385991 0.552482 0.338142 11.00000 0.03393 0.03613 = 0.08320 -0.01103 -0.01376 -0.00342 H13A 2 0.308031 0.633976 0.322086 11.00000 0.06371 C14 1 0.521985 0.508479 0.276907 11.00000 0.04404 0.03895 = 0.06275 0.00495 -0.01099 -0.00887 H14A 2 0.531732 0.551694 0.219830 11.00000 0.06587 C15 1 0.638051 0.393707 0.293501 11.00000 0.03126 0.03656 = 0.04451 -0.00112 -0.00176 -0.00804 H15A 2 0.731007 0.366932 0.252201 11.00000 0.04807 CL2 6 0.507443 -0.182632 0.334703 11.00000 0.06629 0.04176 = 0.05253 -0.00206 -0.01672 -0.01473 C16 1 0.528439 -0.046932 0.365286 11.00000 0.03715 0.04317 = 0.03577 -0.00132 -0.01082 -0.00807 H16A 2 0.565570 -0.067324 0.426258 11.00000 0.04141 H16B 2 0.605247 -0.035353 0.322376 11.00000 0.04479 C17 1 0.374734 0.063833 0.368908 11.00000 0.03250 0.04250 = 0.03513 -0.00263 -0.00334 -0.00947 H17A 2 0.298446 0.046584 0.410514 11.00000 0.03701 H17B 2 0.389368 0.134132 0.390027 11.00000 0.03577 N2 3 0.315585 0.097072 0.278270 11.00000 0.02357 0.04090 = 0.03965 0.00067 -0.00696 -0.01182 H2N 2 0.244343 0.084906 0.270829 11.00000 0.04992 C18 1 0.379290 0.152679 0.211947 11.00000 0.02381 0.03096 = 0.03707 -0.00470 -0.00466 -0.00751 O2 4 0.495365 0.174309 0.221898 11.00000 0.03465 0.06806 = 0.04773 0.00461 -0.01098 -0.02968 P2 5 0.280622 0.194387 0.101538 11.00000 0.02925 0.02969 = 0.03735 -0.00373 -0.00792 -0.00899 C19 1 0.129821 0.343949 0.136430 11.00000 0.02880 0.03100 = 0.04138 0.00135 -0.00014 -0.00873 C20 1 0.141189 0.416423 0.204298 11.00000 0.04616 0.03914 = 0.05313 -0.00864 0.00077 -0.01042 H20A 2 0.233553 0.389801 0.240090 11.00000 0.04935 C21 1 0.018385 0.527251 0.226800 11.00000 0.06480 0.04027 = 0.07282 -0.01802 0.01592 -0.01654 H21A 2 0.029244 0.568779 0.269319 11.00000 0.06828 C22 1 -0.115464 0.566462 0.182349 11.00000 0.04510 0.02994 = 0.10448 0.00796 0.02472 -0.00147 H22A 2 -0.196393 0.638693 0.196348 11.00000 0.06509 C23 1 -0.127643 0.496870 0.114293 11.00000 0.03260 0.04542 = 0.08305 0.01929 -0.00022 -0.00541 H23A 2 -0.220495 0.525018 0.083426 11.00000 0.07351 C24 1 -0.005729 0.385184 0.091775 11.00000 0.03172 0.04258 = 0.05351 0.01162 -0.00632 -0.01153 H24A 2 -0.012008 0.340341 0.049355 11.00000 0.06321 C25 1 0.431181 0.233298 0.026219 11.00000 0.02964 0.03026 = 0.03656 0.00057 -0.00635 -0.00432 C26 1 0.500307 0.164565 -0.053623 11.00000 0.04329 0.04541 = 0.03650 -0.00285 -0.01010 -0.00768 H26A 2 0.470131 0.102538 -0.064856 11.00000 0.06623 C27 1 0.623228 0.181246 -0.110796 11.00000 0.04625 0.06821 = 0.03220 0.00076 -0.00405 -0.00723 H27A 2 0.668738 0.137799 -0.166661 11.00000 0.05947 C28 1 0.677352 0.267701 -0.089487 11.00000 0.04053 0.06532 = 0.04693 0.01811 -0.00180 -0.01217 H28A 2 0.763725 0.276359 -0.130283 11.00000 0.06123 C29 1 0.608911 0.338695 -0.011633 11.00000 0.05073 0.04512 = 0.06977 0.00965 -0.00627 -0.02151 H29A 2 0.644579 0.402151 0.003546 11.00000 0.06691 C30 1 0.486566 0.321636 0.046417 11.00000 0.04288 0.03588 = 0.05094 -0.00540 0.00180 -0.01340 H30A 2 0.443194 0.372536 0.095144 11.00000 0.04453 HKLF 4 REM _2017_32_Process REM R1 = 0.0478 for 5783 Fo > 4sig(Fo) and 0.0546 for all 6564 data REM 463 parameters refined using 0 restraints END WGHT 0.0350 1.1496 REM Instructions for potential hydrogen bonds HTAB C1 O2 HTAB N1 O2 HTAB C11 Cl2_$1 HTAB N2 O1_$2 REM Highest difference peak 0.302, deepest hole -0.416, 1-sigma level 0.052 Q1 1 0.7605 -0.0973 0.1570 11.00000 0.05 0.30 Q2 1 0.6774 0.2591 0.3798 11.00000 0.05 0.27 Q3 1 0.9403 -0.1183 0.1075 11.00000 0.05 0.27 Q4 1 0.5402 0.3376 0.3883 11.00000 0.05 0.23 Q5 1 0.2006 0.2982 0.1159 11.00000 0.05 0.23 Q6 1 0.8434 0.1996 0.4355 11.00000 0.05 0.23 Q7 1 0.9423 0.1656 0.4884 11.00000 0.05 0.22 Q8 1 0.4006 -0.1572 0.3553 11.00000 0.05 0.22 Q9 1 0.8852 0.2404 0.6658 11.00000 0.05 0.22 Q10 1 0.0622 0.3578 0.1138 11.00000 0.05 0.21 Q11 1 1.0250 0.2625 0.5820 11.00000 0.05 0.20 Q12 1 0.9971 0.1763 0.5605 11.00000 0.05 0.20 Q13 1 1.0191 0.3107 0.4351 11.00000 0.05 0.19 Q14 1 0.3401 0.1806 0.1684 11.00000 0.05 0.19 Q15 1 0.4486 0.5182 0.3039 11.00000 0.05 0.18 Q16 1 0.6706 0.2526 0.0974 11.00000 0.05 0.18 Q17 1 0.4594 0.2244 -0.0250 11.00000 0.05 0.18 Q18 1 0.6347 0.1739 -0.2168 11.00000 0.05 0.18 Q19 1 0.9500 0.2392 0.4421 11.00000 0.05 0.17 Q20 1 0.5153 -0.1419 0.2845 11.00000 0.05 0.17 Q21 1 0.4515 0.0110 0.3556 11.00000 0.05 0.17 Q22 1 0.3513 0.0841 0.3198 11.00000 0.05 0.17 Q23 1 0.6482 0.3648 0.3503 11.00000 0.05 0.17 Q24 1 0.2461 0.3426 0.2826 11.00000 0.05 0.17 Q25 1 0.3921 0.4555 0.0822 11.00000 0.05 0.17 ; _shelx_res_checksum 13860 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 Cl1 Cl 0.86327(10) -0.14085(7) 0.14798(6) 0.0627(2) Uani 1 1 d C1 C 0.8225(3) 0.0018(2) 0.08591(17) 0.0399(5) Uani 1 1 d H1A H 0.862(3) -0.016(3) 0.019(2) 0.051(8) Uiso 1 1 d H1B H 0.708(3) 0.042(3) 0.0934(19) 0.050(7) Uiso 1 1 d C2 C 0.8935(3) 0.0797(2) 0.12533(17) 0.0404(5) Uani 1 1 d H2A H 1.002(4) 0.030(3) 0.133(2) 0.055(8) Uiso 1 1 d H2B H 0.879(3) 0.147(3) 0.0872(19) 0.044(7) Uiso 1 1 d N1 N 0.8140(2) 0.12463(19) 0.21669(14) 0.0387(4) Uani 1 1 d H1N H 0.719(3) 0.152(2) 0.2269(19) 0.044(7) Uiso 1 1 d C3 C 0.8894(2) 0.11547(18) 0.29026(15) 0.0297(4) Uani 1 1 d O1 O 1.03323(16) 0.06384(15) 0.28806(12) 0.0399(4) Uani 1 1 d P1 P 0.76414(6) 0.17107(5) 0.40309(4) 0.03063(13) Uani 1 1 d C4 C 0.9002(2) 0.2158(2) 0.45789(15) 0.0324(4) Uani 1 1 d C5 C 0.9642(3) 0.2986(2) 0.41636(18) 0.0387(5) Uani 1 1 d H5A H 0.939(3) 0.338(3) 0.353(2) 0.050(7) Uiso 1 1 d C6 C 1.0641(3) 0.3308(2) 0.4621(2) 0.0459(6) Uani 1 1 d H6A H 1.102(4) 0.388(3) 0.436(2) 0.062(9) Uiso 1 1 d C7 C 1.1002(3) 0.2808(3) 0.5491(2) 0.0512(7) Uani 1 1 d H7A H 1.162(4) 0.303(3) 0.580(2) 0.075(10) Uiso 1 1 d C8 C 1.0388(3) 0.1982(3) 0.59111(19) 0.0521(7) Uani 1 1 d H8A H 1.059(3) 0.160(3) 0.650(2) 0.055(8) Uiso 1 1 d C9 C 0.9386(3) 0.1650(2) 0.54543(17) 0.0418(5) Uani 1 1 d H9A H 0.894(3) 0.108(3) 0.573(2) 0.051(8) Uiso 1 1 d C10 C 0.6181(2) 0.32140(19) 0.37041(15) 0.0310(4) Uani 1 1 d C11 C 0.4797(3) 0.3669(2) 0.43104(18) 0.0413(5) Uani 1 1 d H11A H 0.470(3) 0.318(2) 0.4847(19) 0.040(7) Uiso 1 1 d C12 C 0.3654(3) 0.4824(3) 0.4148(2) 0.0513(7) Uani 1 1 d H12A H 0.279(4) 0.512(3) 0.459(2) 0.066(9) Uiso 1 1 d C13 C 0.3860(3) 0.5525(2) 0.3381(2) 0.0530(7) Uani 1 1 d H13A H 0.308(4) 0.634(3) 0.322(2) 0.064(9) Uiso 1 1 d C14 C 0.5220(3) 0.5085(2) 0.2769(2) 0.0506(6) Uani 1 1 d H14A H 0.532(4) 0.552(3) 0.220(2) 0.066(9) Uiso 1 1 d C15 C 0.6381(3) 0.3937(2) 0.29350(17) 0.0393(5) Uani 1 1 d H15A H 0.731(3) 0.367(3) 0.2522(19) 0.048(7) Uiso 1 1 d Cl2 Cl 0.50744(9) -0.18263(6) 0.33470(5) 0.05436(18) Uani 1 1 d C16 C 0.5284(3) -0.0469(2) 0.36529(18) 0.0403(5) Uani 1 1 d H16A H 0.566(3) -0.067(2) 0.4263(19) 0.041(7) Uiso 1 1 d H16B H 0.605(3) -0.035(2) 0.3224(19) 0.045(7) Uiso 1 1 d C17 C 0.3747(3) 0.0638(2) 0.36891(16) 0.0382(5) Uani 1 1 d H17A H 0.298(3) 0.047(2) 0.4105(18) 0.037(6) Uiso 1 1 d H17B H 0.389(3) 0.134(2) 0.3900(17) 0.036(6) Uiso 1 1 d N2 N 0.3156(2) 0.09707(18) 0.27827(14) 0.0347(4) Uani 1 1 d H2N H 0.244(3) 0.085(3) 0.271(2) 0.050(8) Uiso 1 1 d C18 C 0.3793(2) 0.15268(19) 0.21195(15) 0.0312(4) Uani 1 1 d O2 O 0.49536(18) 0.17431(18) 0.22190(12) 0.0468(4) Uani 1 1 d P2 P 0.28062(6) 0.19439(5) 0.10154(4) 0.03225(13) Uani 1 1 d C19 C 0.1298(2) 0.3439(2) 0.13643(16) 0.0351(5) Uani 1 1 d C20 C 0.1412(3) 0.4164(2) 0.2043(2) 0.0482(6) Uani 1 1 d H20A H 0.234(3) 0.390(3) 0.2401(19) 0.049(7) Uiso 1 1 d C21 C 0.0184(4) 0.5273(3) 0.2268(3) 0.0619(8) Uani 1 1 d H21A H 0.029(4) 0.569(3) 0.269(2) 0.068(10) Uiso 1 1 d C22 C -0.1155(3) 0.5665(3) 0.1823(3) 0.0678(10) Uani 1 1 d H22A H -0.196(4) 0.639(3) 0.196(2) 0.065(9) Uiso 1 1 d C23 C -0.1276(3) 0.4969(3) 0.1143(2) 0.0585(8) Uani 1 1 d H23A H -0.220(4) 0.525(3) 0.083(2) 0.074(10) Uiso 1 1 d C24 C -0.0057(3) 0.3852(2) 0.0918(2) 0.0440(6) Uani 1 1 d H24A H -0.012(4) 0.340(3) 0.049(2) 0.063(10) Uiso 1 1 d C25 C 0.4312(2) 0.23330(19) 0.02622(15) 0.0342(4) Uani 1 1 d C26 C 0.5003(3) 0.1646(2) -0.05362(17) 0.0440(5) Uani 1 1 d H26A H 0.470(4) 0.103(3) -0.065(2) 0.066(9) Uiso 1 1 d C27 C 0.6232(3) 0.1812(3) -0.11080(18) 0.0536(7) Uani 1 1 d H27A H 0.669(3) 0.138(3) -0.167(2) 0.059(8) Uiso 1 1 d C28 C 0.6774(3) 0.2677(3) -0.0895(2) 0.0549(7) Uani 1 1 d H28A H 0.764(4) 0.276(3) -0.130(2) 0.061(9) Uiso 1 1 d C29 C 0.6089(3) 0.3387(3) -0.0116(2) 0.0550(7) Uani 1 1 d H29A H 0.645(4) 0.402(3) 0.004(2) 0.067(9) Uiso 1 1 d C30 C 0.4866(3) 0.3216(2) 0.04642(19) 0.0443(5) Uani 1 1 d H30A H 0.443(3) 0.373(3) 0.0951(19) 0.045(7) Uiso 1 1 d 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 0.0801(5) 0.0471(4) 0.0636(5) 0.0010(3) -0.0134(4) -0.0261(4) C1 0.0404(12) 0.0472(14) 0.0313(12) -0.0056(10) -0.0083(9) -0.0138(10) C2 0.0412(12) 0.0464(14) 0.0348(12) -0.0059(10) -0.0035(9) -0.0175(11) N1 0.0254(9) 0.0476(11) 0.0414(11) -0.0144(9) -0.0051(8) -0.0094(8) C3 0.0261(9) 0.0278(10) 0.0385(11) -0.0032(8) -0.0052(8) -0.0130(8) O1 0.0226(7) 0.0489(10) 0.0472(9) -0.0070(7) -0.0049(6) -0.0114(6) P1 0.0281(2) 0.0320(3) 0.0334(3) -0.0017(2) -0.0028(2) -0.0134(2) C4 0.0283(9) 0.0333(11) 0.0340(11) -0.0072(8) -0.0053(8) -0.0085(8) C5 0.0339(11) 0.0410(12) 0.0438(13) -0.0063(10) -0.0072(9) -0.0154(9) C6 0.0347(11) 0.0453(14) 0.0608(16) -0.0180(12) -0.0056(11) -0.0157(10) C7 0.0330(11) 0.0595(17) 0.0587(17) -0.0301(13) -0.0125(11) -0.0075(11) C8 0.0447(13) 0.0599(17) 0.0395(14) -0.0135(12) -0.0161(11) -0.0010(12) C9 0.0395(12) 0.0406(13) 0.0381(12) -0.0043(10) -0.0080(10) -0.0059(10) C10 0.0243(9) 0.0323(11) 0.0383(11) -0.0080(8) -0.0046(8) -0.0115(8) C11 0.0334(11) 0.0497(14) 0.0432(13) -0.0122(11) 0.0033(9) -0.0190(10) C12 0.0277(11) 0.0511(16) 0.0710(19) -0.0266(14) 0.0040(11) -0.0093(10) C13 0.0339(12) 0.0361(13) 0.083(2) -0.0110(13) -0.0138(12) -0.0034(10) C14 0.0440(13) 0.0390(13) 0.0628(18) 0.0050(12) -0.0110(12) -0.0089(11) C15 0.0313(10) 0.0366(12) 0.0445(13) -0.0011(10) -0.0018(9) -0.0080(9) Cl2 0.0663(4) 0.0418(3) 0.0525(4) -0.0021(3) -0.0167(3) -0.0147(3) C16 0.0372(11) 0.0432(13) 0.0358(12) -0.0013(10) -0.0108(10) -0.0081(10) C17 0.0325(10) 0.0425(13) 0.0351(12) -0.0026(10) -0.0033(9) -0.0095(10) N2 0.0236(8) 0.0409(10) 0.0397(10) 0.0007(8) -0.0070(7) -0.0118(8) C18 0.0238(9) 0.0310(10) 0.0371(11) -0.0047(8) -0.0047(8) -0.0075(8) O2 0.0346(8) 0.0681(12) 0.0477(10) 0.0046(8) -0.0110(7) -0.0297(8) P2 0.0292(3) 0.0297(3) 0.0373(3) -0.0037(2) -0.0079(2) -0.0090(2) C19 0.0288(10) 0.0310(11) 0.0414(12) 0.0013(9) -0.0001(8) -0.0087(8) C20 0.0462(13) 0.0391(13) 0.0531(15) -0.0086(11) 0.0008(11) -0.0104(11) C21 0.0648(18) 0.0403(15) 0.073(2) -0.0180(14) 0.0159(16) -0.0165(14) C22 0.0451(15) 0.0299(13) 0.104(3) 0.0080(15) 0.0247(16) -0.0015(12) C23 0.0326(12) 0.0454(16) 0.083(2) 0.0193(15) -0.0002(13) -0.0054(11) C24 0.0317(11) 0.0426(13) 0.0535(15) 0.0116(12) -0.0063(10) -0.0115(10) C25 0.0296(10) 0.0303(11) 0.0366(11) 0.0006(8) -0.0064(8) -0.0043(8) C26 0.0433(12) 0.0454(14) 0.0365(12) -0.0028(10) -0.0101(10) -0.0077(11) C27 0.0462(14) 0.0682(19) 0.0322(13) 0.0008(12) -0.0040(11) -0.0072(13) C28 0.0405(13) 0.0653(18) 0.0469(15) 0.0181(13) -0.0018(11) -0.0122(13) C29 0.0507(15) 0.0451(15) 0.0698(19) 0.0096(13) -0.0063(13) -0.0215(12) C30 0.0429(12) 0.0359(12) 0.0509(15) -0.0054(11) 0.0018(11) -0.0134(10) 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' P P 0.1023 0.0942 '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 C2 C1 Cl1 111.69(17) C2 C1 H1A 112.0(16) Cl1 C1 H1A 107.9(16) C2 C1 H1B 110.0(16) Cl1 C1 H1B 105.1(16) H1A C1 H1B 110(2) N1 C2 C1 111.6(2) N1 C2 H2A 107.4(17) C1 C2 H2A 109.1(17) N1 C2 H2B 106.7(17) C1 C2 H2B 107.9(17) H2A C2 H2B 114(2) C3 N1 C2 123.30(19) C3 N1 H1N 115.4(19) C2 N1 H1N 121.1(19) O1 C3 N1 122.9(2) O1 C3 P1 120.38(16) N1 C3 P1 116.42(15) C4 P1 C10 101.86(9) C4 P1 C3 98.62(9) C10 P1 C3 103.32(9) C9 C4 C5 119.2(2) C9 C4 P1 117.72(18) C5 C4 P1 123.11(17) C6 C5 C4 120.5(2) C6 C5 H5A 117.6(15) C4 C5 H5A 121.9(15) C7 C6 C5 119.9(3) C7 C6 H6A 120(2) C5 C6 H6A 120(2) C6 C7 C8 120.5(2) C6 C7 H7A 120(2) C8 C7 H7A 119(2) C7 C8 C9 120.0(3) C7 C8 H8A 125.0(18) C9 C8 H8A 115.0(18) C4 C9 C8 120.0(3) C4 C9 H9A 118.4(17) C8 C9 H9A 121.7(17) C15 C10 C11 118.3(2) C15 C10 P1 125.45(16) C11 C10 P1 116.22(18) C12 C11 C10 120.5(2) C12 C11 H11A 122.2(16) C10 C11 H11A 117.2(16) C13 C12 C11 120.6(2) C13 C12 H12A 122(2) C11 C12 H12A 118(2) C12 C13 C14 119.7(2) C12 C13 H13A 124.3(18) C14 C13 H13A 116.0(18) C13 C14 C15 120.0(3) C13 C14 H14A 120.1(19) C15 C14 H14A 119(2) C10 C15 C14 120.9(2) C10 C15 H15A 120.5(17) C14 C15 H15A 118.6(17) C17 C16 Cl2 112.10(17) C17 C16 H16A 111.3(15) Cl2 C16 H16A 103.8(15) C17 C16 H16B 111.8(17) Cl2 C16 H16B 107.5(17) H16A C16 H16B 110(2) N2 C17 C16 112.76(19) N2 C17 H17A 108.0(15) C16 C17 H17A 109.1(15) N2 C17 H17B 107.6(15) C16 C17 H17B 109.6(14) H17A C17 H17B 110(2) C18 N2 C17 121.55(19) C18 N2 H2N 120(2) C17 N2 H2N 118(2) O2 C18 N2 122.0(2) O2 C18 P2 122.79(17) N2 C18 P2 115.21(15) C19 P2 C25 103.94(10) C19 P2 C18 98.20(10) C25 P2 C18 98.63(9) C24 C19 C20 118.9(2) C24 C19 P2 116.40(19) C20 C19 P2 124.72(18) C21 C20 C19 120.0(3) C21 C20 H20A 117.8(16) C19 C20 H20A 122.1(16) C22 C21 C20 120.4(3) C22 C21 H21A 122(2) C20 C21 H21A 117(2) C23 C22 C21 120.3(3) C23 C22 H22A 118(2) C21 C22 H22A 121(2) C22 C23 C24 119.7(3) C22 C23 H23A 120(2) C24 C23 H23A 120(2) C23 C24 C19 120.7(3) C23 C24 H24A 121(2) C19 C24 H24A 119(2) C26 C25 C30 118.3(2) C26 C25 P2 117.13(18) C30 C25 P2 124.42(18) C27 C26 C25 121.1(3) C27 C26 H26A 120(2) C25 C26 H26A 119(2) C28 C27 C26 119.8(3) C28 C27 H27A 117.8(18) C26 C27 H27A 122.2(18) C27 C28 C29 120.2(3) C27 C28 H28A 117.8(19) C29 C28 H28A 122.0(19) C28 C29 C30 120.2(3) C28 C29 H29A 121.1(19) C30 C29 H29A 118.7(19) C29 C30 C25 120.3(3) C29 C30 H30A 116.7(17) C25 C30 H30A 122.9(17) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C1 1.776(3) C1 C2 1.505(3) C1 H1A 0.99(3) C1 H1B 0.97(3) C2 N1 1.452(3) C2 H2A 0.97(3) C2 H2B 0.90(3) N1 C3 1.328(3) N1 H1N 0.81(3) C3 O1 1.231(2) C3 P1 1.870(2) P1 C4 1.835(2) P1 C10 1.840(2) C4 C9 1.389(3) C4 C5 1.391(3) C5 C6 1.388(3) C5 H5A 1.01(3) C6 C7 1.375(4) C6 H6A 0.91(3) C7 C8 1.377(4) C7 H7A 0.89(3) C8 C9 1.397(4) C8 H8A 0.94(3) C9 H9A 0.96(3) C10 C15 1.386(3) C10 C11 1.392(3) C11 C12 1.391(4) C11 H11A 0.95(3) C12 C13 1.369(4) C12 H12A 0.93(3) C13 C14 1.380(4) C13 H13A 0.99(3) C14 C15 1.393(3) C14 H14A 0.95(3) C15 H15A 0.94(3) Cl2 C16 1.784(3) C16 C17 1.512(3) C16 H16A 0.97(3) C16 H16B 0.92(3) C17 N2 1.457(3) C17 H17A 0.94(2) C17 H17B 0.97(3) N2 C18 1.324(3) N2 H2N 0.75(3) C18 O2 1.230(2) C18 P2 1.887(2) P2 C19 1.831(2) P2 C25 1.834(2) C19 C24 1.392(3) C19 C20 1.392(3) C20 C21 1.386(4) C20 H20A 0.99(3) C21 C22 1.378(5) C21 H21A 0.86(3) C22 C23 1.373(5) C22 H22A 0.91(3) C23 C24 1.389(4) C23 H23A 0.96(3) C24 H24A 0.86(3) C25 C26 1.393(3) C25 C30 1.396(3) C26 C27 1.385(4) C26 H26A 0.91(3) C27 C28 1.373(4) C27 H27A 0.95(3) C28 C29 1.382(4) C28 H28A 0.96(3) C29 C30 1.389(4) C29 H29A 0.98(3) C30 H30A 0.91(3) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1 H1B O2 0.97(3) 2.61(3) 3.378(3) 135(2) . N1 H1N O2 0.81(3) 2.00(3) 2.777(2) 160(3) . C11 H11A Cl2 0.95(3) 2.94(3) 3.873(3) 167(2) 2_656 N2 H2N O1 0.75(3) 2.05(3) 2.785(2) 164(3) 1_455 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 Cl1 C1 C2 N1 -69.8(2) C1 C2 N1 C3 130.6(2) C2 N1 C3 O1 -2.8(4) C2 N1 C3 P1 -176.58(18) O1 C3 P1 C4 34.42(19) N1 C3 P1 C4 -151.63(17) O1 C3 P1 C10 138.86(17) N1 C3 P1 C10 -47.19(18) C10 P1 C4 C9 129.30(18) C3 P1 C4 C9 -125.04(18) C10 P1 C4 C5 -49.9(2) C3 P1 C4 C5 55.7(2) C9 C4 C5 C6 -0.5(3) P1 C4 C5 C6 178.67(18) C4 C5 C6 C7 0.0(4) C5 C6 C7 C8 0.4(4) C6 C7 C8 C9 -0.2(4) C5 C4 C9 C8 0.7(3) P1 C4 C9 C8 -178.52(18) C7 C8 C9 C4 -0.4(4) C4 P1 C10 C15 78.5(2) C3 P1 C10 C15 -23.4(2) C4 P1 C10 C11 -98.59(17) C3 P1 C10 C11 159.45(16) C15 C10 C11 C12 -0.4(3) P1 C10 C11 C12 176.93(18) C10 C11 C12 C13 0.9(4) C11 C12 C13 C14 -0.5(4) C12 C13 C14 C15 -0.5(4) C11 C10 C15 C14 -0.5(3) P1 C10 C15 C14 -177.62(19) C13 C14 C15 C10 1.0(4) Cl2 C16 C17 N2 -64.2(2) C16 C17 N2 C18 -75.0(3) C17 N2 C18 O2 3.2(3) C17 N2 C18 P2 -177.42(16) O2 C18 P2 C19 -94.0(2) N2 C18 P2 C19 86.55(17) O2 C18 P2 C25 11.5(2) N2 C18 P2 C25 -167.90(16) C25 P2 C19 C24 103.61(18) C18 P2 C19 C24 -155.32(18) C25 P2 C19 C20 -77.4(2) C18 P2 C19 C20 23.7(2) C24 C19 C20 C21 0.4(4) P2 C19 C20 C21 -178.6(2) C19 C20 C21 C22 0.0(4) C20 C21 C22 C23 -0.9(5) C21 C22 C23 C24 1.4(4) C22 C23 C24 C19 -1.0(4) C20 C19 C24 C23 0.1(4) P2 C19 C24 C23 179.21(19) C19 P2 C25 C26 -139.46(18) C18 P2 C25 C26 119.80(18) C19 P2 C25 C30 44.4(2) C18 P2 C25 C30 -56.4(2) C30 C25 C26 C27 1.3(3) P2 C25 C26 C27 -175.10(19) C25 C26 C27 C28 -0.7(4) C26 C27 C28 C29 -0.5(4) C27 C28 C29 C30 1.0(4) C28 C29 C30 C25 -0.4(4) C26 C25 C30 C29 -0.7(4) P2 C25 C30 C29 175.4(2)