#------------------------------------------------------------------------------ #$Date: 2020-10-06 10:19:08 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257350 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/74/1557428.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_1557428 loop_ _publ_author_name 'Zhuang, Zeyan' 'Dai, Jun' 'Yu, Maoxing' 'Li, Jianqing' 'Shen, Pingchuan' 'Hu, Rong' 'Lou, Xiaoding' 'Zhao, Zujin' 'Tang, Ben Zhong' _publ_section_title ; Type I photosensitizers based on phosphindole oxide for photodynamic therapy: apoptosis and autophagy induced by endoplasmic reticulum stress ; _journal_issue 13 _journal_name_full 'Chemical Science' _journal_page_first 3405 _journal_page_last 3417 _journal_paper_doi 10.1039/D0SC00785D _journal_volume 11 _journal_year 2020 _chemical_formula_moiety 'C33 H27 N2 O2 P' _chemical_formula_sum 'C33 H27 N2 O2 P' _chemical_formula_weight 514.53 _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 _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-08-06 deposited with the CCDC. 2020-02-21 downloaded from the CCDC. ; _cell_angle_alpha 71.708(2) _cell_angle_beta 65.4407(19) _cell_angle_gamma 89.239(2) _cell_formula_units_Z 2 _cell_length_a 10.6898(7) _cell_length_b 11.7750(8) _cell_length_c 11.9913(7) _cell_measurement_reflns_used 5820 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 25.09 _cell_measurement_theta_min 2.20 _cell_volume 1291.40(15) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'PHOTON 100 CMOS detector' _diffrn_measurement_method 'omega scan' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_unetI/netI 0.0580 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 4543 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.025 _diffrn_reflns_theta_max 25.025 _diffrn_reflns_theta_min 2.114 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.141 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_correction_T_min 0.6722 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'TWINABS (Bruker, 2012)' _exptl_crystal_density_diffrn 1.323 _exptl_crystal_description block _exptl_crystal_F_000 540 _exptl_crystal_size_max 0.370 _exptl_crystal_size_mid 0.330 _exptl_crystal_size_min 0.180 _refine_diff_density_max 0.270 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.060 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 345 _refine_ls_number_reflns 4543 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.038 _refine_ls_R_factor_all 0.0899 _refine_ls_R_factor_gt 0.0597 _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^)+(0.0433P)^2^+1.7064P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1164 _refine_ls_wR_factor_ref 0.1316 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3587 _reflns_number_total 4543 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sc00785d2.cif _cod_data_source_block 1 _cod_depositor_comments ;Adding full bibliography for 1557428--1557429.cif. Adding full bibliography for 1557428--1557429.cif. ; _cod_database_code 1557428 _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 0.950 _shelx_estimated_absorpt_t_max 0.975 _shelx_res_file ; 1.res created by SHELXL-2014/7 TITL 1 in P-1 CELL 0.71073 10.68980 11.77500 11.99130 71.7077 65.4407 89.2387 ZERR 2.00 0.00070 0.00080 0.00070 0.0022 0.0019 0.0024 LATT 1 SFAC C H N O P UNIT 66 54 4 4 2 L.S. 10 BOND $h acta size 0.37 0.33 0.18 omit -2 50.05 FMAP 2 PLAN 20 TEMP -100.150 WGHT 0.043276 1.706410 BASF 0.22139 FVAR 0.71722 MOLE 1 C1 1 0.824980 0.678371 0.387111 11.00000 0.02103 0.02455 = 0.01747 -0.00345 -0.00942 0.00325 C2 1 0.908091 0.768945 0.380255 11.00000 0.02137 0.02045 = 0.02151 -0.00665 -0.01141 0.00286 C3 1 0.833709 0.858592 0.438871 11.00000 0.02385 0.02172 = 0.02189 -0.00821 -0.01350 0.00589 C4 1 0.688241 0.832537 0.495698 11.00000 0.02543 0.02211 = 0.02169 -0.00529 -0.01184 0.00509 C5 1 0.604238 0.907613 0.551956 11.00000 0.02200 0.03569 = 0.02566 -0.01275 -0.01074 0.00956 AFIX 43 H5 2 0.506104 0.888342 0.591018 11.00000 -1.20000 AFIX 0 C6 1 0.664653 1.012162 0.551005 11.00000 0.03297 0.03003 = 0.03059 -0.01692 -0.01525 0.01258 AFIX 43 H6 2 0.607818 1.065139 0.588834 11.00000 -1.20000 AFIX 0 C7 1 0.806749 1.038466 0.495173 11.00000 0.03085 0.02638 = 0.03619 -0.01319 -0.01622 0.00305 AFIX 43 H7 2 0.847242 1.110199 0.494413 11.00000 -1.20000 AFIX 0 C8 1 0.892404 0.962277 0.439811 11.00000 0.02345 0.02871 = 0.02670 -0.00973 -0.01116 0.00356 AFIX 43 H8 2 0.990446 0.981139 0.402893 11.00000 -1.20000 AFIX 0 C9 1 0.666185 0.568928 0.690462 11.00000 0.05101 0.03877 = 0.03588 -0.00226 -0.02128 -0.00214 AFIX 23 H9A 2 0.693483 0.644591 0.699141 11.00000 -1.20000 H9B 2 0.751650 0.536330 0.646063 11.00000 -1.20000 AFIX 0 C10 1 0.579128 0.479485 0.822023 11.00000 0.06194 0.04406 = 0.03520 -0.00126 -0.00836 0.00745 AFIX 137 H10A 2 0.494311 0.511975 0.865040 11.00000 -1.50000 H10B 2 0.631390 0.463611 0.874590 11.00000 -1.50000 H10C 2 0.554510 0.404126 0.812839 11.00000 -1.50000 AFIX 0 C11 1 0.910738 0.390163 0.227809 11.00000 0.01850 0.02668 = 0.02937 -0.01344 -0.01316 0.00693 C12 1 1.017638 0.479061 0.193879 11.00000 0.01885 0.02913 = 0.02898 -0.01337 -0.00873 0.00497 AFIX 43 H12 2 1.108955 0.476937 0.133301 11.00000 -1.20000 AFIX 0 C13 1 0.992714 0.570224 0.247074 11.00000 0.02035 0.02725 = 0.02982 -0.01042 -0.01173 -0.00021 AFIX 43 H13 2 1.067922 0.628794 0.223056 11.00000 -1.20000 AFIX 0 C14 1 0.859614 0.578765 0.335481 11.00000 0.01910 0.02266 = 0.01909 -0.00748 -0.00809 0.00261 C15 1 0.753916 0.487297 0.370185 11.00000 0.02185 0.02972 = 0.02695 -0.01484 -0.00766 0.00593 AFIX 43 H15 2 0.662395 0.489111 0.430610 11.00000 -1.20000 AFIX 0 C16 1 0.778678 0.395283 0.319519 11.00000 0.01738 0.03153 = 0.03572 -0.01426 -0.01025 -0.00119 AFIX 43 H16 2 0.704725 0.333971 0.347286 11.00000 -1.20000 AFIX 0 C17 1 1.074112 0.267908 0.120146 11.00000 0.02376 0.02422 = 0.02883 -0.01155 -0.01391 0.00560 C18 1 1.141487 0.276894 -0.008991 11.00000 0.03561 0.04009 = 0.03422 -0.01614 -0.02068 0.01078 AFIX 43 H18 2 1.096444 0.304119 -0.064306 11.00000 -1.20000 AFIX 0 C19 1 1.274459 0.246493 -0.058690 11.00000 0.03366 0.03916 = 0.02973 -0.01543 -0.00806 0.00468 AFIX 43 H19 2 1.319922 0.251667 -0.147433 11.00000 -1.20000 AFIX 0 C20 1 1.340421 0.208743 0.021141 11.00000 0.02262 0.02895 = 0.03997 -0.01282 -0.01013 0.00506 AFIX 43 H20 2 1.432132 0.189006 -0.012851 11.00000 -1.20000 AFIX 0 C21 1 1.273263 0.199574 0.150610 11.00000 0.02593 0.02622 = 0.03696 -0.00637 -0.01696 0.00334 AFIX 43 H21 2 1.318728 0.172658 0.205595 11.00000 -1.20000 AFIX 0 C22 1 1.140574 0.229236 0.200674 11.00000 0.02121 0.02727 = 0.02652 -0.01089 -0.00890 0.00189 AFIX 43 H22 2 1.094964 0.223245 0.289660 11.00000 -1.20000 AFIX 0 C23 1 0.831890 0.240107 0.157321 11.00000 0.02414 0.03074 = 0.02382 -0.01377 -0.01182 0.00509 C24 1 0.732498 0.300959 0.126169 11.00000 0.02609 0.03374 = 0.02910 -0.01024 -0.01356 0.00431 AFIX 43 H24 2 0.734882 0.385173 0.111541 11.00000 -1.20000 AFIX 0 C25 1 0.630002 0.240149 0.116217 11.00000 0.02290 0.05253 = 0.03071 -0.01387 -0.01452 0.00378 AFIX 43 H25 2 0.562234 0.282839 0.095310 11.00000 -1.20000 AFIX 0 C26 1 0.625272 0.118195 0.136351 11.00000 0.02976 0.05057 = 0.03554 -0.02292 -0.01530 -0.00245 AFIX 43 H26 2 0.553927 0.076722 0.130380 11.00000 -1.20000 AFIX 0 C27 1 0.724392 0.056762 0.165150 11.00000 0.04575 0.03462 = 0.03984 -0.01964 -0.01656 -0.00227 AFIX 43 H27 2 0.722022 -0.027195 0.178253 11.00000 -1.20000 AFIX 0 C28 1 0.828219 0.117311 0.175152 11.00000 0.03480 0.03425 = 0.03627 -0.01743 -0.02094 0.00868 AFIX 43 H28 2 0.896917 0.074583 0.194248 11.00000 -1.20000 AFIX 0 C29 1 1.282528 0.896945 0.161033 11.00000 0.02715 0.02771 = 0.03347 -0.01284 -0.00194 -0.00150 AFIX 43 H29 2 1.333756 0.959773 0.080496 11.00000 -1.20000 AFIX 0 C30 1 1.139846 0.878554 0.207202 11.00000 0.02709 0.02983 = 0.03238 -0.01011 -0.01144 0.00851 AFIX 43 H30 2 1.095261 0.927798 0.159439 11.00000 -1.20000 AFIX 0 C31 1 1.062906 0.787183 0.324216 11.00000 0.02042 0.01891 = 0.02431 -0.01230 -0.00799 0.00207 C32 1 1.134718 0.718234 0.388818 11.00000 0.02382 0.02434 = 0.02730 -0.00938 -0.01049 0.00469 AFIX 43 H32 2 1.086338 0.654110 0.468931 11.00000 -1.20000 AFIX 0 C33 1 1.277783 0.744347 0.334735 11.00000 0.02505 0.04179 = 0.04007 -0.02297 -0.01722 0.01087 AFIX 43 H33 2 1.325273 0.696869 0.380473 11.00000 -1.20000 AFIX 0 N1 3 0.936264 0.299780 0.170690 11.00000 0.02077 0.03485 = 0.03936 -0.02345 -0.01719 0.00956 N2 3 1.352949 0.832142 0.222289 11.00000 0.02121 0.04027 = 0.03921 -0.02310 -0.00769 0.00330 O1 4 0.549857 0.699368 0.415808 11.00000 0.02538 0.04970 = 0.04628 -0.02581 -0.02218 0.00964 O2 4 0.586984 0.593156 0.614755 11.00000 0.02618 0.02955 = 0.02980 -0.01181 -0.00591 -0.00311 P1 5 0.644893 0.696070 0.476161 11.00000 0.01735 0.02846 = 0.02712 -0.01274 -0.00872 0.00332 HKLF 5 REM 1 in P-1 REM R1 = 0.0597 for 3587 Fo > 4sig(Fo) and 0.0899 for all 4543 data REM 345 parameters refined using 0 restraints END WGHT 0.0244 1.1838 REM Highest difference peak 0.270, deepest hole -0.284, 1-sigma level 0.060 Q1 1 0.7613 0.8167 0.5025 11.00000 0.05 0.27 Q2 1 0.4410 0.5443 0.7380 11.00000 0.05 0.26 Q3 1 0.6257 0.6452 0.7472 11.00000 0.05 0.26 Q4 1 0.4597 0.7435 0.6436 11.00000 0.05 0.25 Q5 1 0.7510 0.8660 0.4229 11.00000 0.05 0.24 Q6 1 0.9034 0.1418 0.1119 11.00000 0.05 0.23 Q7 1 0.5219 0.6578 0.3777 11.00000 0.05 0.23 Q8 1 0.8586 0.8235 0.3934 11.00000 0.05 0.23 Q9 1 0.5000 1.0000 0.5000 10.50000 0.05 0.22 Q10 1 1.1023 0.7003 0.5245 11.00000 0.05 0.22 Q11 1 1.1632 0.1155 0.2049 11.00000 0.05 0.21 Q12 1 1.3419 0.7373 0.4099 11.00000 0.05 0.21 Q13 1 1.0949 0.8777 0.1357 11.00000 0.05 0.20 Q14 1 0.6030 0.6547 0.4279 11.00000 0.05 0.20 Q15 1 1.1219 0.2800 0.1517 11.00000 0.05 0.20 Q16 1 1.1052 0.9390 0.3245 11.00000 0.05 0.20 Q17 1 0.5279 0.4880 0.6822 11.00000 0.05 0.20 Q18 1 0.8402 0.4227 0.2383 11.00000 0.05 0.20 Q19 1 0.8618 0.2033 0.1154 11.00000 0.05 0.20 Q20 1 1.0164 0.9378 0.1487 11.00000 0.05 0.20 ; _shelx_res_checksum 64367 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 C1 C 0.8250(3) 0.6784(3) 0.3871(3) 0.0216(7) Uani 1 1 d . . . . . C2 C 0.9081(3) 0.7689(3) 0.3803(3) 0.0205(7) Uani 1 1 d . . . . . C3 C 0.8337(3) 0.8586(3) 0.4389(3) 0.0210(7) Uani 1 1 d . . . . . C4 C 0.6882(3) 0.8325(3) 0.4957(3) 0.0231(7) Uani 1 1 d . . . . . C5 C 0.6042(4) 0.9076(3) 0.5520(3) 0.0271(8) Uani 1 1 d . . . . . H5 H 0.5061 0.8883 0.5910 0.033 Uiso 1 1 calc R U . . . C6 C 0.6647(4) 1.0122(3) 0.5510(4) 0.0290(8) Uani 1 1 d . . . . . H6 H 0.6078 1.0651 0.5888 0.035 Uiso 1 1 calc R U . . . C7 C 0.8067(4) 1.0385(3) 0.4952(4) 0.0298(8) Uani 1 1 d . . . . . H7 H 0.8472 1.1102 0.4944 0.036 Uiso 1 1 calc R U . . . C8 C 0.8924(4) 0.9623(3) 0.4398(3) 0.0261(8) Uani 1 1 d . . . . . H8 H 0.9904 0.9811 0.4029 0.031 Uiso 1 1 calc R U . . . C9 C 0.6662(4) 0.5689(4) 0.6905(4) 0.0436(11) Uani 1 1 d . . . . . H9A H 0.6935 0.6446 0.6991 0.052 Uiso 1 1 calc R U . . . H9B H 0.7517 0.5363 0.6461 0.052 Uiso 1 1 calc R U . . . C10 C 0.5791(5) 0.4795(4) 0.8220(4) 0.0548(13) Uani 1 1 d . . . . . H10A H 0.4943 0.5120 0.8650 0.082 Uiso 1 1 calc R U . . . H10B H 0.6314 0.4636 0.8746 0.082 Uiso 1 1 calc R U . . . H10C H 0.5545 0.4041 0.8128 0.082 Uiso 1 1 calc R U . . . C11 C 0.9107(3) 0.3902(3) 0.2278(3) 0.0229(8) Uani 1 1 d . . . . . C12 C 1.0176(3) 0.4791(3) 0.1939(3) 0.0253(8) Uani 1 1 d . . . . . H12 H 1.1090 0.4769 0.1333 0.030 Uiso 1 1 calc R U . . . C13 C 0.9927(3) 0.5702(3) 0.2471(3) 0.0253(8) Uani 1 1 d . . . . . H13 H 1.0679 0.6288 0.2231 0.030 Uiso 1 1 calc R U . . . C14 C 0.8596(3) 0.5788(3) 0.3355(3) 0.0202(7) Uani 1 1 d . . . . . C15 C 0.7539(3) 0.4873(3) 0.3702(3) 0.0259(8) Uani 1 1 d . . . . . H15 H 0.6624 0.4891 0.4306 0.031 Uiso 1 1 calc R U . . . C16 C 0.7787(3) 0.3953(3) 0.3195(4) 0.0279(8) Uani 1 1 d . . . . . H16 H 0.7047 0.3340 0.3473 0.033 Uiso 1 1 calc R U . . . C17 C 1.0741(3) 0.2679(3) 0.1201(3) 0.0241(8) Uani 1 1 d . . . . . C18 C 1.1415(4) 0.2769(4) -0.0090(4) 0.0338(9) Uani 1 1 d . . . . . H18 H 1.0964 0.3041 -0.0643 0.041 Uiso 1 1 calc R U . . . C19 C 1.2745(4) 0.2465(4) -0.0587(4) 0.0352(9) Uani 1 1 d . . . . . H19 H 1.3199 0.2517 -0.1474 0.042 Uiso 1 1 calc R U . . . C20 C 1.3404(4) 0.2087(3) 0.0211(4) 0.0315(9) Uani 1 1 d . . . . . H20 H 1.4321 0.1890 -0.0129 0.038 Uiso 1 1 calc R U . . . C21 C 1.2733(4) 0.1996(3) 0.1506(4) 0.0296(8) Uani 1 1 d . . . . . H21 H 1.3187 0.1727 0.2056 0.036 Uiso 1 1 calc R U . . . C22 C 1.1406(3) 0.2292(3) 0.2007(3) 0.0250(8) Uani 1 1 d . . . . . H22 H 1.0950 0.2232 0.2897 0.030 Uiso 1 1 calc R U . . . C23 C 0.8319(3) 0.2401(3) 0.1573(3) 0.0246(8) Uani 1 1 d . . . . . C24 C 0.7325(4) 0.3010(3) 0.1262(3) 0.0292(8) Uani 1 1 d . . . . . H24 H 0.7349 0.3852 0.1115 0.035 Uiso 1 1 calc R U . . . C25 C 0.6300(4) 0.2401(4) 0.1162(4) 0.0344(9) Uani 1 1 d . . . . . H25 H 0.5622 0.2828 0.0953 0.041 Uiso 1 1 calc R U . . . C26 C 0.6253(4) 0.1182(4) 0.1364(4) 0.0360(9) Uani 1 1 d . . . . . H26 H 0.5539 0.0767 0.1304 0.043 Uiso 1 1 calc R U . . . C27 C 0.7244(4) 0.0568(4) 0.1651(4) 0.0389(10) Uani 1 1 d . . . . . H27 H 0.7220 -0.0272 0.1783 0.047 Uiso 1 1 calc R U . . . C28 C 0.8282(4) 0.1173(3) 0.1752(4) 0.0317(9) Uani 1 1 d . . . . . H28 H 0.8969 0.0746 0.1942 0.038 Uiso 1 1 calc R U . . . C29 C 1.2825(4) 0.8969(3) 0.1610(4) 0.0328(9) Uani 1 1 d . . . . . H29 H 1.3338 0.9598 0.0805 0.039 Uiso 1 1 calc R U . . . C30 C 1.1398(4) 0.8786(3) 0.2072(4) 0.0304(9) Uani 1 1 d . . . . . H30 H 1.0953 0.9278 0.1594 0.037 Uiso 1 1 calc R U . . . C31 C 1.0629(3) 0.7872(3) 0.3242(3) 0.0205(7) Uani 1 1 d . . . . . C32 C 1.1347(3) 0.7182(3) 0.3888(3) 0.0252(8) Uani 1 1 d . . . . . H32 H 1.0863 0.6541 0.4689 0.030 Uiso 1 1 calc R U . . . C33 C 1.2778(4) 0.7443(4) 0.3347(4) 0.0322(9) Uani 1 1 d . . . . . H33 H 1.3253 0.6969 0.3805 0.039 Uiso 1 1 calc R U . . . N1 N 0.9363(3) 0.2998(3) 0.1707(3) 0.0274(7) Uani 1 1 d . . . . . N2 N 1.3529(3) 0.8321(3) 0.2223(3) 0.0330(8) Uani 1 1 d . . . . . O1 O 0.5499(2) 0.6994(2) 0.4158(3) 0.0356(7) Uani 1 1 d . . . . . O2 O 0.5870(2) 0.5932(2) 0.6148(2) 0.0302(6) Uani 1 1 d . . . . . P1 P 0.64489(9) 0.69607(9) 0.47616(9) 0.0238(2) Uani 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 C1 0.0210(17) 0.0246(18) 0.0175(17) -0.0034(15) -0.0094(14) 0.0033(14) C2 0.0214(17) 0.0204(18) 0.0215(18) -0.0067(15) -0.0114(15) 0.0029(14) C3 0.0239(17) 0.0217(18) 0.0219(18) -0.0082(15) -0.0135(15) 0.0059(14) C4 0.0254(18) 0.0221(18) 0.0217(18) -0.0053(15) -0.0118(15) 0.0051(14) C5 0.0220(18) 0.036(2) 0.0257(19) -0.0128(17) -0.0107(16) 0.0096(16) C6 0.033(2) 0.030(2) 0.031(2) -0.0169(17) -0.0153(17) 0.0126(16) C7 0.031(2) 0.026(2) 0.036(2) -0.0132(18) -0.0162(18) 0.0031(16) C8 0.0234(18) 0.029(2) 0.027(2) -0.0097(16) -0.0112(16) 0.0036(15) C9 0.051(3) 0.039(2) 0.036(2) -0.002(2) -0.021(2) -0.002(2) C10 0.062(3) 0.044(3) 0.035(3) -0.001(2) -0.008(2) 0.007(2) C11 0.0185(17) 0.0267(19) 0.0294(19) -0.0134(16) -0.0132(15) 0.0069(14) C12 0.0188(17) 0.029(2) 0.029(2) -0.0134(17) -0.0087(15) 0.0050(15) C13 0.0203(18) 0.027(2) 0.030(2) -0.0104(16) -0.0117(16) -0.0002(15) C14 0.0191(17) 0.0227(18) 0.0191(17) -0.0075(15) -0.0081(14) 0.0026(14) C15 0.0218(18) 0.030(2) 0.0270(19) -0.0148(17) -0.0077(15) 0.0059(15) C16 0.0174(17) 0.032(2) 0.036(2) -0.0143(17) -0.0102(16) -0.0012(15) C17 0.0238(18) 0.0242(19) 0.0288(19) -0.0116(16) -0.0139(15) 0.0056(15) C18 0.036(2) 0.040(2) 0.034(2) -0.0161(19) -0.0207(18) 0.0108(18) C19 0.034(2) 0.039(2) 0.030(2) -0.0154(18) -0.0081(18) 0.0047(18) C20 0.0226(18) 0.029(2) 0.040(2) -0.0128(18) -0.0101(17) 0.0051(16) C21 0.0259(19) 0.026(2) 0.037(2) -0.0064(17) -0.0170(17) 0.0033(15) C22 0.0212(17) 0.027(2) 0.0265(19) -0.0109(16) -0.0089(15) 0.0019(15) C23 0.0241(18) 0.031(2) 0.0238(18) -0.0138(16) -0.0118(15) 0.0051(15) C24 0.0261(19) 0.034(2) 0.029(2) -0.0102(17) -0.0136(16) 0.0043(16) C25 0.0229(19) 0.053(3) 0.031(2) -0.0139(19) -0.0145(16) 0.0038(18) C26 0.030(2) 0.051(3) 0.036(2) -0.023(2) -0.0153(18) -0.0025(18) C27 0.046(2) 0.035(2) 0.040(2) -0.020(2) -0.017(2) -0.0023(19) C28 0.035(2) 0.034(2) 0.036(2) -0.0174(18) -0.0209(18) 0.0087(17) C29 0.027(2) 0.028(2) 0.033(2) -0.0128(18) -0.0019(17) -0.0015(16) C30 0.0271(19) 0.030(2) 0.032(2) -0.0101(18) -0.0114(17) 0.0085(16) C31 0.0204(17) 0.0189(17) 0.0243(18) -0.0123(15) -0.0080(15) 0.0021(14) C32 0.0238(18) 0.0243(19) 0.0273(19) -0.0094(16) -0.0105(16) 0.0047(15) C33 0.025(2) 0.042(2) 0.040(2) -0.023(2) -0.0172(18) 0.0109(17) N1 0.0208(15) 0.0348(18) 0.0394(18) -0.0234(15) -0.0172(14) 0.0096(13) N2 0.0212(15) 0.040(2) 0.039(2) -0.0231(17) -0.0077(15) 0.0033(15) O1 0.0254(14) 0.0497(17) 0.0463(17) -0.0258(14) -0.0222(12) 0.0096(12) O2 0.0262(13) 0.0295(14) 0.0298(14) -0.0118(12) -0.0059(11) -0.0031(11) P1 0.0173(4) 0.0285(5) 0.0271(5) -0.0127(4) -0.0087(4) 0.0033(4) 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' 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 C2 C1 C14 130.7(3) . . ? C2 C1 P1 108.6(2) . . ? C14 C1 P1 120.7(2) . . ? C1 C2 C3 115.1(3) . . ? C1 C2 C31 127.9(3) . . ? C3 C2 C31 117.0(3) . . ? C8 C3 C4 118.8(3) . . ? C8 C3 C2 127.1(3) . . ? C4 C3 C2 114.0(3) . . ? C5 C4 C3 121.3(3) . . ? C5 C4 P1 130.5(3) . . ? C3 C4 P1 108.3(2) . . ? C4 C5 C6 119.3(3) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C7 C6 C5 119.8(3) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C6 C7 C8 121.3(3) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C3 C8 C7 119.5(3) . . ? C3 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? O2 C9 C10 108.9(3) . . ? O2 C9 H9A 109.9 . . ? C10 C9 H9A 109.9 . . ? O2 C9 H9B 109.9 . . ? C10 C9 H9B 109.9 . . ? H9A C9 H9B 108.3 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 117.5(3) . . ? C12 C11 N1 120.6(3) . . ? C16 C11 N1 121.9(3) . . ? C13 C12 C11 121.0(3) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 121.9(3) . . ? C12 C13 H13 119.0 . . ? C14 C13 H13 119.0 . . ? C15 C14 C13 116.2(3) . . ? C15 C14 C1 119.4(3) . . ? C13 C14 C1 124.3(3) . . ? C16 C15 C14 122.0(3) . . ? C16 C15 H15 119.0 . . ? C14 C15 H15 119.0 . . ? C15 C16 C11 121.2(3) . . ? C15 C16 H16 119.4 . . ? C11 C16 H16 119.4 . . ? C18 C17 C22 119.7(3) . . ? C18 C17 N1 120.0(3) . . ? C22 C17 N1 120.2(3) . . ? C17 C18 C19 120.5(3) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C20 C19 C18 119.7(4) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C21 120.0(3) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C22 C21 C20 120.5(3) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 C17 119.6(3) . . ? C21 C22 H22 120.2 . . ? C17 C22 H22 120.2 . . ? C24 C23 C28 118.6(3) . . ? C24 C23 N1 121.7(3) . . ? C28 C23 N1 119.7(3) . . ? C25 C24 C23 120.6(4) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C26 C25 C24 120.6(4) . . ? C26 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C27 C26 C25 119.7(3) . . ? C27 C26 H26 120.2 . . ? C25 C26 H26 120.2 . . ? C26 C27 C28 120.2(4) . . ? C26 C27 H27 119.9 . . ? C28 C27 H27 119.9 . . ? C27 C28 C23 120.4(3) . . ? C27 C28 H28 119.8 . . ? C23 C28 H28 119.8 . . ? N2 C29 C30 124.2(4) . . ? N2 C29 H29 117.9 . . ? C30 C29 H29 117.9 . . ? C29 C30 C31 119.0(4) . . ? C29 C30 H30 120.5 . . ? C31 C30 H30 120.5 . . ? C30 C31 C32 117.6(3) . . ? C30 C31 C2 120.3(3) . . ? C32 C31 C2 122.1(3) . . ? C33 C32 C31 119.0(3) . . ? C33 C32 H32 120.5 . . ? C31 C32 H32 120.5 . . ? N2 C33 C32 123.9(3) . . ? N2 C33 H33 118.0 . . ? C32 C33 H33 118.0 . . ? C11 N1 C23 122.6(3) . . ? C11 N1 C17 119.4(3) . . ? C23 N1 C17 118.0(3) . . ? C33 N2 C29 116.3(3) . . ? C9 O2 P1 120.9(2) . . ? O1 P1 O2 110.78(15) . . ? O1 P1 C4 117.23(16) . . ? O2 P1 C4 107.58(14) . . ? O1 P1 C1 118.70(15) . . ? O2 P1 C1 106.95(15) . . ? C4 P1 C1 93.97(15) . . ? 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 C1 C2 1.358(5) . ? C1 C14 1.466(5) . ? C1 P1 1.819(3) . ? C2 C3 1.490(5) . ? C2 C31 1.494(4) . ? C3 C8 1.385(5) . ? C3 C4 1.406(4) . ? C4 C5 1.376(5) . ? C4 P1 1.788(3) . ? C5 C6 1.392(5) . ? C5 H5 0.9500 . ? C6 C7 1.374(5) . ? C6 H6 0.9500 . ? C7 C8 1.389(5) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 O2 1.446(5) . ? C9 C10 1.492(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.395(5) . ? C11 C16 1.398(5) . ? C11 N1 1.404(4) . ? C12 C13 1.382(5) . ? C12 H12 0.9500 . ? C13 C14 1.403(4) . ? C13 H13 0.9500 . ? C14 C15 1.404(5) . ? C15 C16 1.373(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.378(5) . ? C17 C22 1.389(5) . ? C17 N1 1.437(4) . ? C18 C19 1.386(5) . ? C18 H18 0.9500 . ? C19 C20 1.377(5) . ? C19 H19 0.9500 . ? C20 C21 1.381(5) . ? C20 H20 0.9500 . ? C21 C22 1.380(5) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.387(5) . ? C23 C28 1.392(5) . ? C23 N1 1.416(4) . ? C24 C25 1.382(5) . ? C24 H24 0.9500 . ? C25 C26 1.377(5) . ? C25 H25 0.9500 . ? C26 C27 1.376(6) . ? C26 H26 0.9500 . ? C27 C28 1.393(5) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 N2 1.335(5) . ? C29 C30 1.383(5) . ? C29 H29 0.9500 . ? C30 C31 1.385(5) . ? C30 H30 0.9500 . ? C31 C32 1.390(5) . ? C32 C33 1.385(5) . ? C32 H32 0.9500 . ? C33 N2 1.334(5) . ? C33 H33 0.9500 . ? O1 P1 1.466(3) . ? O2 P1 1.586(3) . ?