#------------------------------------------------------------------------------ #$Date: 2020-10-06 10:19:08 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257350 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/74/1557429.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_1557429 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 100.850(2) _cell_angle_beta 100.343(2) _cell_angle_gamma 93.057(2) _cell_formula_units_Z 2 _cell_length_a 9.1957(6) _cell_length_b 10.8410(7) _cell_length_c 13.3381(8) _cell_measurement_reflns_used 2513 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 24.84 _cell_measurement_theta_min 2.50 _cell_volume 1279.46(14) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.993 _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_R_equivalents 0.0725 _diffrn_reflns_av_unetI/netI 0.0844 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 12612 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.353 _diffrn_reflns_theta_min 2.261 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.142 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_correction_T_min 0.6510 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 2012)' _exptl_crystal_density_diffrn 1.336 _exptl_crystal_description sheet _exptl_crystal_F_000 540 _exptl_crystal_size_max 0.290 _exptl_crystal_size_mid 0.170 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.282 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.051 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 428 _refine_ls_number_reflns 4637 _refine_ls_number_restraints 299 _refine_ls_restrained_S_all 1.021 _refine_ls_R_factor_all 0.1091 _refine_ls_R_factor_gt 0.0499 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0235P)^2^+0.4096P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0814 _refine_ls_wR_factor_ref 0.0961 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2840 _reflns_number_total 4637 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sc00785d2.cif _cod_data_source_block 1_CCDC1 _cod_depositor_comments ;Adding full bibliography for 1557428--1557429.cif. Adding full bibliography for 1557428--1557429.cif. ; _cod_database_code 1557429 _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 0.960 _shelx_estimated_absorpt_t_max 0.993 _shelx_res_file ; 1.res created by SHELXL-2014/7 TITL 1 in P-1 CELL 0.71073 9.1957 10.8410 13.3381 100.850 100.343 93.057 ZERR 2.00 0.0006 0.0007 0.0008 0.002 0.002 0.002 LATT 1 SFAC C H N O P UNIT 66 54 4 4 2 L.S. 10 ACTA BOND $H FMAP 2 PLAN 20 simu .02 .03 o2 > c10' sadi o2 c10 o2' c10' dfix 1.53 c9 c10 c9' c10' sadi .02 o2 c9 o2' c9' sadi p1 c9 p1 c9' sadi .02 p1 o2 p1 o2' size 0.29 0.17 0.05 TEMP -100.150 WGHT 0.023470 0.409550 FVAR 0.15179 0.79171 0.62269 MOLE 1 C1 1 1.070878 0.837034 0.370833 11.00000 0.02604 0.02335 = 0.02242 0.00203 0.00304 0.00318 C2 1 1.013251 0.868353 0.279812 11.00000 0.02473 0.02332 = 0.02094 0.00135 0.00217 0.00310 C3 1 1.118764 0.951011 0.241680 11.00000 0.02345 0.02398 = 0.02686 0.00402 0.00885 0.00195 C4 1 1.261031 0.974205 0.304395 11.00000 0.02202 0.02386 = 0.02711 0.00258 0.00613 0.00168 C5 1 1.369228 1.053196 0.283387 11.00000 0.02802 0.03066 = 0.03559 0.00039 0.00801 -0.00124 AFIX 43 H5 2 1.465729 1.066919 0.325691 11.00000 -1.20000 AFIX 0 C6 1 1.335107 1.112342 0.199565 11.00000 0.03267 0.03066 = 0.04143 0.00508 0.01703 -0.00508 AFIX 43 H6 2 1.408430 1.167401 0.184471 11.00000 -1.20000 AFIX 0 C7 1 1.195657 1.091526 0.138359 11.00000 0.04224 0.03393 = 0.03074 0.01376 0.01358 0.00299 AFIX 43 H7 2 1.173424 1.133235 0.081602 11.00000 -1.20000 AFIX 0 C8 1 1.085665 1.010059 0.157975 11.00000 0.03051 0.03276 = 0.02446 0.00719 0.00563 0.00233 AFIX 43 H8 2 0.989932 0.995522 0.114602 11.00000 -1.20000 AFIX 0 C17 1 0.570824 0.735865 0.116669 11.00000 0.02142 0.02796 = 0.02660 0.00727 0.00319 0.00078 C18 1 0.689419 0.723802 0.064729 11.00000 0.02817 0.02664 = 0.02154 0.00478 0.00417 0.00137 AFIX 43 H18 2 0.672871 0.683214 -0.006481 11.00000 -1.20000 AFIX 0 C19 1 0.831690 0.770960 0.116806 11.00000 0.02372 0.03055 = 0.02137 0.00631 0.00815 0.00287 AFIX 43 H19 2 0.911731 0.763218 0.080504 11.00000 -1.20000 AFIX 0 C20 1 0.858976 0.829533 0.221599 11.00000 0.02495 0.02122 = 0.02396 0.00518 0.00342 0.00063 C21 1 0.739331 0.843274 0.272404 11.00000 0.02817 0.02993 = 0.02470 0.00082 0.00769 0.00047 AFIX 43 H21 2 0.755214 0.884344 0.343469 11.00000 -1.20000 AFIX 0 C22 1 0.597129 0.797240 0.219660 11.00000 0.02348 0.03684 = 0.03040 0.00665 0.01014 0.00338 AFIX 43 H22 2 0.516311 0.808105 0.254993 11.00000 -1.20000 AFIX 0 C23 1 0.362424 0.727956 -0.026930 11.00000 0.01773 0.03279 = 0.02430 0.00719 0.00508 0.00082 C24 1 0.289819 0.644057 -0.115830 11.00000 0.02819 0.03225 = 0.03170 0.00281 0.00585 -0.00099 AFIX 43 H24 2 0.280902 0.556215 -0.116374 11.00000 -1.20000 AFIX 0 C25 1 0.230557 0.688308 -0.203475 11.00000 0.03924 0.04504 = 0.02860 -0.00069 -0.00087 -0.00431 AFIX 43 H25 2 0.179680 0.630708 -0.263909 11.00000 -1.20000 AFIX 0 C26 1 0.244557 0.815456 -0.204088 11.00000 0.03006 0.05703 = 0.03247 0.01730 -0.00327 0.00095 AFIX 43 H26 2 0.205765 0.845286 -0.265160 11.00000 -1.20000 AFIX 0 C27 1 0.315123 0.898664 -0.115574 11.00000 0.02961 0.03356 = 0.04654 0.01504 0.00021 0.00241 AFIX 43 H27 2 0.323985 0.986459 -0.115228 11.00000 -1.20000 AFIX 0 C28 1 0.372813 0.855506 -0.027729 11.00000 0.02774 0.02917 = 0.03175 0.00100 0.00140 -0.00015 AFIX 43 H28 2 0.420433 0.913899 0.033237 11.00000 -1.20000 AFIX 0 C29 1 0.338571 0.609401 0.111681 11.00000 0.02535 0.02484 = 0.02668 0.00321 0.00578 -0.00036 C30 1 0.406179 0.536724 0.179236 11.00000 0.02835 0.03056 = 0.03381 0.00552 0.00306 0.00270 AFIX 43 H30 2 0.511278 0.537810 0.193961 11.00000 -1.20000 AFIX 0 C31 1 0.321573 0.463290 0.224820 11.00000 0.05040 0.03226 = 0.03391 0.01151 0.00319 0.00039 AFIX 43 H31 2 0.369216 0.415427 0.271834 11.00000 -1.20000 AFIX 0 C32 1 0.169176 0.458137 0.203363 11.00000 0.05240 0.04437 = 0.03750 0.01630 0.01466 -0.01246 AFIX 43 H32 2 0.111398 0.406023 0.234072 11.00000 -1.20000 AFIX 0 C33 1 0.101881 0.529765 0.136658 11.00000 0.02802 0.05712 = 0.04283 0.01790 0.00841 -0.00693 AFIX 43 H33 2 -0.003340 0.527051 0.121385 11.00000 -1.20000 AFIX 0 C34 1 0.185122 0.605620 0.091537 11.00000 0.02540 0.03972 = 0.03591 0.01471 0.00519 0.00286 AFIX 43 H34 2 0.136851 0.655452 0.046453 11.00000 -1.20000 AFIX 0 N2 3 0.425366 0.683820 0.063751 11.00000 0.01999 0.03973 = 0.03005 0.01312 0.00114 -0.00435 O1 4 1.312294 0.969270 0.517885 11.00000 0.03736 0.03751 = 0.02652 -0.00316 0.00111 0.00084 P1 5 1.264583 0.895218 0.411610 11.00000 0.02689 0.02962 = 0.02593 0.00463 0.00226 0.00155 PART 1 O2 4 1.356498 0.779302 0.383994 21.00000 0.02264 0.03541 = 0.02720 0.00423 0.00231 0.00751 C9 1 1.474858 0.739996 0.453597 21.00000 0.03003 0.03437 = 0.03339 0.00974 -0.00004 0.01029 AFIX 23 H9A 2 1.537042 0.815509 0.496415 21.00000 -1.20000 H9B 2 1.538149 0.689189 0.412334 21.00000 -1.20000 AFIX 0 C10 1 1.419462 0.664002 0.523741 21.00000 0.07910 0.04750 = 0.04814 0.02230 0.01469 -0.00152 AFIX 137 H10A 2 1.363017 0.715969 0.568586 21.00000 -1.50000 H10B 2 1.503894 0.635616 0.566886 21.00000 -1.50000 H10C 2 1.355123 0.590551 0.481783 21.00000 -1.50000 PART 2 AFIX 0 O2' 4 1.326574 0.762861 0.389437 -21.00000 0.03878 0.02293 = 0.04997 0.00442 0.00077 0.01035 C9' 1 1.370404 0.690576 0.467665 -21.00000 0.04485 0.04552 = 0.04317 0.01030 0.01800 0.00964 AFIX 23 H9'1 2 1.314272 0.606346 0.447015 -21.00000 -1.20000 H9'2 2 1.346425 0.733328 0.534324 -21.00000 -1.20000 AFIX 0 C10' 1 1.535572 0.675556 0.482257 -21.00000 0.07008 0.06090 = 0.06448 0.01171 0.00752 0.00781 AFIX 137 H10D 2 1.562035 0.646083 0.414341 -21.00000 -1.50000 H10E 2 1.560074 0.613923 0.526400 -21.00000 -1.50000 H10F 2 1.591257 0.756963 0.515453 -21.00000 -1.50000 PART 0 AFIX 0 sadi .02 c1 c13 c1 c13' sadi c1 c12 c1 c14 c1 c12' c1 c14' flat c13 > c12 c1 flat c13' > c12' c1 simu .02 c13 > c12' part 3 same c13 c12 < c14 same c13' > c12' same c13' c12' < c14' C13 1 0.991578 0.762646 0.429502 31.00000 0.03210 0.02706 = 0.02297 0.00555 0.00237 0.00505 C14 1 0.910662 0.647421 0.384747 31.00000 0.04484 0.03153 = 0.02632 0.00468 0.00628 0.00091 AFIX 43 H14 2 0.908596 0.610530 0.313954 31.00000 -1.20000 AFIX 0 C15 1 0.833440 0.587077 0.443837 31.00000 0.05387 0.03421 = 0.03830 0.00771 0.01191 -0.01116 AFIX 43 H15 2 0.780898 0.507593 0.411567 31.00000 -1.20000 AFIX 0 N1 3 0.827051 0.631965 0.542807 31.00000 0.04701 0.03789 = 0.02970 0.00919 0.01193 -0.00178 C11 1 0.911069 0.740189 0.586472 31.00000 0.04957 0.04037 = 0.02487 0.00434 0.01350 0.00743 AFIX 43 H11 2 0.914470 0.772343 0.658292 31.00000 -1.20000 AFIX 0 C12 1 0.993032 0.808439 0.534925 31.00000 0.02682 0.03009 = 0.02288 0.00596 -0.00064 -0.00175 AFIX 43 H12 2 1.049406 0.885152 0.570477 31.00000 -1.20000 AFIX 0 part 4 C13' 1 0.999646 0.761764 0.433366 -31.00000 0.02807 0.02831 = 0.02155 0.01067 0.00282 -0.00066 C14' 1 0.962470 0.632867 0.400436 -31.00000 0.04920 0.02658 = 0.02474 0.00565 0.01296 0.00050 AFIX 43 H14' 2 0.980700 0.589763 0.335604 -31.00000 -1.20000 AFIX 0 C15' 1 0.898236 0.568456 0.464116 -31.00000 0.05158 0.02846 = 0.03315 0.00018 0.00479 -0.00273 AFIX 43 H15' 2 0.870340 0.480847 0.439332 -31.00000 -1.20000 AFIX 0 N1' 3 0.872584 0.619760 0.557278 -31.00000 0.05516 0.03673 = 0.03233 0.00520 0.01124 -0.00812 C11' 1 0.902821 0.745420 0.587295 -31.00000 0.04539 0.03117 = 0.03477 0.01010 0.00620 0.00118 AFIX 43 H11' 2 0.876348 0.786923 0.649914 -31.00000 -1.20000 AFIX 0 C12' 1 0.971310 0.816248 0.529846 -31.00000 0.03880 0.02469 = 0.03060 0.00915 0.00646 0.00940 AFIX 43 H12' 2 0.999309 0.903450 0.556909 -31.00000 -1.20000 part 0 AFIX 0 HKLF 4 REM 1 in P-1 REM R1 = 0.0499 for 2840 Fo > 4sig(Fo) and 0.1091 for all 4637 data REM 428 parameters refined using 299 restraints END WGHT 0.0339 0.4742 REM Highest difference peak 0.282, deepest hole -0.272, 1-sigma level 0.051 Q1 1 1.0666 0.9257 0.2577 11.00000 0.05 0.28 Q2 1 1.2578 0.9353 0.3452 11.00000 0.05 0.25 Q3 1 1.0875 1.0054 0.2218 11.00000 0.05 0.25 Q4 1 0.9228 0.8414 0.2428 11.00000 0.05 0.24 Q5 1 1.1591 0.8669 0.4147 11.00000 0.05 0.23 Q6 1 1.1890 0.9563 0.2680 11.00000 0.05 0.23 Q7 1 0.5049 0.7020 0.0813 11.00000 0.05 0.20 Q8 1 0.8158 0.8815 0.2462 11.00000 0.05 0.19 Q9 1 0.2776 0.6865 -0.0568 11.00000 0.05 0.19 Q10 1 0.3843 0.6834 -0.0780 11.00000 0.05 0.18 Q11 1 1.3565 0.7801 0.5824 11.00000 0.05 0.18 Q12 1 1.1318 0.9231 0.1998 11.00000 0.05 0.18 Q13 1 1.3098 0.9651 0.2845 11.00000 0.05 0.17 Q14 1 0.3755 0.6503 0.1192 11.00000 0.05 0.17 Q15 1 1.5300 1.0297 0.2744 11.00000 0.05 0.17 Q16 1 0.2570 0.6845 0.1221 11.00000 0.05 0.17 Q17 1 0.3314 0.8464 -0.1602 11.00000 0.05 0.17 Q18 1 1.2344 0.9130 0.5428 11.00000 0.05 0.17 Q19 1 1.2631 1.1519 0.2062 11.00000 0.05 0.17 Q20 1 0.6568 0.7774 0.2559 11.00000 0.05 0.17 ; _shelx_res_checksum 73875 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 1.0709(3) 0.8370(2) 0.37083(18) 0.0245(6) Uani 1 1 d D . . . . C2 C 1.0133(3) 0.8684(2) 0.27981(18) 0.0237(6) Uani 1 1 d . . . . . C3 C 1.1188(3) 0.9510(2) 0.24168(19) 0.0244(6) Uani 1 1 d . . . . . C4 C 1.2610(3) 0.9742(2) 0.30440(19) 0.0245(6) Uani 1 1 d . . . . . C5 C 1.3692(3) 1.0532(2) 0.2834(2) 0.0322(7) Uani 1 1 d . . . . . H5 H 1.4657 1.0669 0.3257 0.039 Uiso 1 1 calc R U . . . C6 C 1.3351(3) 1.1123(2) 0.1996(2) 0.0342(7) Uani 1 1 d . . . . . H6 H 1.4084 1.1674 0.1845 0.041 Uiso 1 1 calc R U . . . C7 C 1.1957(3) 1.0915(2) 0.1384(2) 0.0339(7) Uani 1 1 d . . . . . H7 H 1.1734 1.1332 0.0816 0.041 Uiso 1 1 calc R U . . . C8 C 1.0857(3) 1.0101(2) 0.15798(19) 0.0290(6) Uani 1 1 d . . . . . H8 H 0.9899 0.9955 0.1146 0.035 Uiso 1 1 calc R U . . . C17 C 0.5708(3) 0.7359(2) 0.11667(19) 0.0253(6) Uani 1 1 d . . . . . C18 C 0.6894(3) 0.7238(2) 0.06473(19) 0.0256(6) Uani 1 1 d . . . . . H18 H 0.6729 0.6832 -0.0065 0.031 Uiso 1 1 calc R U . . . C19 C 0.8317(3) 0.7710(2) 0.11681(18) 0.0246(6) Uani 1 1 d . . . . . H19 H 0.9117 0.7632 0.0805 0.029 Uiso 1 1 calc R U . . . C20 C 0.8590(3) 0.8295(2) 0.22160(18) 0.0235(6) Uani 1 1 d . . . . . C21 C 0.7393(3) 0.8433(2) 0.27240(19) 0.0280(6) Uani 1 1 d . . . . . H21 H 0.7552 0.8843 0.3435 0.034 Uiso 1 1 calc R U . . . C22 C 0.5971(3) 0.7972(2) 0.21966(19) 0.0296(7) Uani 1 1 d . . . . . H22 H 0.5163 0.8081 0.2550 0.036 Uiso 1 1 calc R U . . . C23 C 0.3624(3) 0.7280(2) -0.02693(18) 0.0247(6) Uani 1 1 d . . . . . C24 C 0.2898(3) 0.6441(3) -0.11583(19) 0.0313(7) Uani 1 1 d . . . . . H24 H 0.2809 0.5562 -0.1164 0.038 Uiso 1 1 calc R U . . . C25 C 0.2306(3) 0.6883(3) -0.2035(2) 0.0400(8) Uani 1 1 d . . . . . H25 H 0.1797 0.6307 -0.2639 0.048 Uiso 1 1 calc R U . . . C26 C 0.2446(3) 0.8155(3) -0.2041(2) 0.0400(8) Uani 1 1 d . . . . . H26 H 0.2058 0.8453 -0.2652 0.048 Uiso 1 1 calc R U . . . C27 C 0.3151(3) 0.8987(3) -0.1156(2) 0.0366(7) Uani 1 1 d . . . . . H27 H 0.3240 0.9865 -0.1152 0.044 Uiso 1 1 calc R U . . . C28 C 0.3728(3) 0.8555(2) -0.0277(2) 0.0309(7) Uani 1 1 d . . . . . H28 H 0.4204 0.9139 0.0332 0.037 Uiso 1 1 calc R U . . . C29 C 0.3386(3) 0.6094(2) 0.11168(19) 0.0259(6) Uani 1 1 d . . . . . C30 C 0.4062(3) 0.5367(2) 0.1792(2) 0.0314(7) Uani 1 1 d . . . . . H30 H 0.5113 0.5378 0.1940 0.038 Uiso 1 1 calc R U . . . C31 C 0.3216(3) 0.4633(3) 0.2248(2) 0.0390(7) Uani 1 1 d . . . . . H31 H 0.3692 0.4154 0.2718 0.047 Uiso 1 1 calc R U . . . C32 C 0.1692(3) 0.4581(3) 0.2034(2) 0.0436(8) Uani 1 1 d . . . . . H32 H 0.1114 0.4060 0.2341 0.052 Uiso 1 1 calc R U . . . C33 C 0.1019(3) 0.5298(3) 0.1367(2) 0.0418(8) Uani 1 1 d . . . . . H33 H -0.0033 0.5271 0.1214 0.050 Uiso 1 1 calc R U . . . C34 C 0.1851(3) 0.6056(2) 0.0915(2) 0.0328(7) Uani 1 1 d . . . . . H34 H 0.1369 0.6555 0.0465 0.039 Uiso 1 1 calc R U . . . N2 N 0.4254(2) 0.6838(2) 0.06375(16) 0.0298(5) Uani 1 1 d . . . . . O1 O 1.31229(19) 0.96927(16) 0.51788(13) 0.0358(5) Uani 1 1 d . . . . . P1 P 1.26458(8) 0.89522(7) 0.41161(5) 0.02801(19) Uani 1 1 d D . . . . O2 O 1.3565(7) 0.7793(5) 0.3840(4) 0.0288(14) Uani 0.792(7) 1 d D U P A 1 C9 C 1.4749(4) 0.7400(4) 0.4536(3) 0.0327(11) Uani 0.792(7) 1 d D U P A 1 H9A H 1.5370 0.8155 0.4964 0.039 Uiso 0.792(7) 1 calc R U P A 1 H9B H 1.5381 0.6892 0.4123 0.039 Uiso 0.792(7) 1 calc R U P A 1 C10 C 1.4195(6) 0.6640(4) 0.5237(3) 0.0565(15) Uani 0.792(7) 1 d D U P A 1 H10A H 1.3630 0.7160 0.5686 0.085 Uiso 0.792(7) 1 calc R U P A 1 H10B H 1.5039 0.6356 0.5669 0.085 Uiso 0.792(7) 1 calc R U P A 1 H10C H 1.3551 0.5906 0.4818 0.085 Uiso 0.792(7) 1 calc R U P A 1 O2' O 1.327(3) 0.763(2) 0.3894(18) 0.038(6) Uani 0.208(7) 1 d D U P A 2 C9' C 1.3704(17) 0.6906(14) 0.4677(12) 0.043(4) Uani 0.208(7) 1 d D U P A 2 H9'1 H 1.3143 0.6063 0.4470 0.052 Uiso 0.208(7) 1 calc R U P A 2 H9'2 H 1.3464 0.7333 0.5343 0.052 Uiso 0.208(7) 1 calc R U P A 2 C10' C 1.5356(16) 0.6756(17) 0.4823(14) 0.066(5) Uani 0.208(7) 1 d D U P A 2 H10D H 1.5620 0.6461 0.4143 0.099 Uiso 0.208(7) 1 calc R U P A 2 H10E H 1.5601 0.6139 0.5264 0.099 Uiso 0.208(7) 1 calc R U P A 2 H10F H 1.5913 0.7570 0.5155 0.099 Uiso 0.208(7) 1 calc R U P A 2 C13 C 0.9916(14) 0.7626(9) 0.4295(8) 0.028(3) Uani 0.62(2) 1 d D U P B 3 C14 C 0.9107(12) 0.6474(7) 0.3847(7) 0.035(2) Uani 0.62(2) 1 d D U P B 3 H14 H 0.9086 0.6105 0.3140 0.041 Uiso 0.62(2) 1 calc R U P B 3 C15 C 0.8334(14) 0.5871(8) 0.4438(7) 0.042(2) Uani 0.62(2) 1 d D U P B 3 H15 H 0.7809 0.5076 0.4116 0.051 Uiso 0.62(2) 1 calc R U P B 3 N1 N 0.8271(12) 0.6320(10) 0.5428(7) 0.038(2) Uani 0.62(2) 1 d D U P B 3 C11 C 0.911(2) 0.7402(12) 0.5865(11) 0.038(3) Uani 0.62(2) 1 d D U P B 3 H11 H 0.9145 0.7723 0.6583 0.045 Uiso 0.62(2) 1 calc R U P B 3 C12 C 0.9930(17) 0.8084(12) 0.5349(7) 0.027(3) Uani 0.62(2) 1 d D U P B 3 H12 H 1.0494 0.8852 0.5705 0.033 Uiso 0.62(2) 1 calc R U P B 3 C13' C 1.000(2) 0.7618(14) 0.4334(12) 0.026(4) Uani 0.38(2) 1 d D U P B 4 C14' C 0.9625(19) 0.6329(11) 0.4004(11) 0.033(3) Uani 0.38(2) 1 d D U P B 4 H14' H 0.9807 0.5898 0.3356 0.039 Uiso 0.38(2) 1 calc R U P B 4 C15' C 0.898(2) 0.5685(12) 0.4641(10) 0.039(3) Uani 0.38(2) 1 d D U P B 4 H15' H 0.8703 0.4808 0.4393 0.047 Uiso 0.38(2) 1 calc R U P B 4 N1' N 0.873(2) 0.6198(17) 0.5573(12) 0.042(3) Uani 0.38(2) 1 d D U P B 4 C11' C 0.903(4) 0.7454(19) 0.5873(17) 0.037(4) Uani 0.38(2) 1 d D U P B 4 H11' H 0.8763 0.7869 0.6499 0.044 Uiso 0.38(2) 1 calc R U P B 4 C12' C 0.971(3) 0.816(2) 0.5298(13) 0.031(4) Uani 0.38(2) 1 d D U P B 4 H12' H 0.9993 0.9035 0.5569 0.037 Uiso 0.38(2) 1 calc R U P B 4 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 0.0260(15) 0.0234(15) 0.0224(14) 0.0020(11) 0.0030(11) 0.0032(12) C2 0.0247(15) 0.0233(15) 0.0209(14) 0.0014(11) 0.0022(11) 0.0031(12) C3 0.0234(15) 0.0240(15) 0.0269(15) 0.0040(11) 0.0088(12) 0.0020(12) C4 0.0220(15) 0.0239(15) 0.0271(14) 0.0026(11) 0.0061(12) 0.0017(12) C5 0.0280(16) 0.0307(16) 0.0356(17) 0.0004(13) 0.0080(13) -0.0012(13) C6 0.0327(17) 0.0307(17) 0.0414(17) 0.0051(13) 0.0170(14) -0.0051(13) C7 0.0422(19) 0.0339(17) 0.0307(16) 0.0138(13) 0.0136(14) 0.0030(14) C8 0.0305(16) 0.0328(16) 0.0245(14) 0.0072(12) 0.0056(12) 0.0023(13) C17 0.0214(15) 0.0280(15) 0.0266(15) 0.0073(11) 0.0032(12) 0.0008(12) C18 0.0282(16) 0.0266(15) 0.0215(14) 0.0048(11) 0.0042(12) 0.0014(12) C19 0.0237(15) 0.0305(15) 0.0214(14) 0.0063(11) 0.0082(11) 0.0029(12) C20 0.0250(15) 0.0212(14) 0.0240(14) 0.0052(11) 0.0034(11) 0.0006(11) C21 0.0282(16) 0.0299(16) 0.0247(15) 0.0008(12) 0.0077(12) 0.0005(12) C22 0.0235(15) 0.0368(17) 0.0304(16) 0.0067(13) 0.0101(12) 0.0034(13) C23 0.0177(14) 0.0328(16) 0.0243(14) 0.0072(12) 0.0051(11) 0.0008(12) C24 0.0282(16) 0.0322(16) 0.0317(16) 0.0028(13) 0.0058(13) -0.0010(13) C25 0.0392(19) 0.045(2) 0.0286(16) -0.0007(14) -0.0009(13) -0.0043(15) C26 0.0301(17) 0.057(2) 0.0325(17) 0.0173(15) -0.0033(13) 0.0009(15) C27 0.0296(17) 0.0336(17) 0.0465(18) 0.0150(14) 0.0002(14) 0.0024(13) C28 0.0277(16) 0.0292(16) 0.0317(16) 0.0010(12) 0.0014(12) -0.0001(12) C29 0.0253(15) 0.0248(15) 0.0267(14) 0.0032(12) 0.0058(12) -0.0004(12) C30 0.0283(16) 0.0306(16) 0.0338(16) 0.0055(13) 0.0031(13) 0.0027(13) C31 0.050(2) 0.0323(17) 0.0339(17) 0.0115(13) 0.0032(15) 0.0004(15) C32 0.052(2) 0.0444(19) 0.0375(18) 0.0163(15) 0.0147(15) -0.0125(16) C33 0.0280(17) 0.057(2) 0.0428(18) 0.0179(16) 0.0084(14) -0.0069(15) C34 0.0254(16) 0.0397(17) 0.0359(16) 0.0147(13) 0.0052(13) 0.0029(13) N2 0.0200(12) 0.0397(14) 0.0300(13) 0.0131(10) 0.0011(10) -0.0044(10) O1 0.0374(12) 0.0375(12) 0.0265(11) -0.0032(8) 0.0011(9) 0.0008(9) P1 0.0269(4) 0.0296(4) 0.0259(4) 0.0046(3) 0.0023(3) 0.0016(3) O2 0.023(2) 0.035(2) 0.0272(18) 0.0042(16) 0.0023(15) 0.0075(19) C9 0.030(2) 0.034(2) 0.033(2) 0.0097(17) 0.0000(18) 0.0103(18) C10 0.079(4) 0.047(3) 0.048(3) 0.022(2) 0.015(3) -0.002(2) O2' 0.039(10) 0.023(7) 0.050(8) 0.004(6) 0.001(7) 0.010(7) C9' 0.045(8) 0.046(8) 0.043(8) 0.010(7) 0.018(7) 0.010(7) C10' 0.070(11) 0.061(11) 0.064(11) 0.012(9) 0.008(9) 0.008(9) C13 0.032(5) 0.027(5) 0.023(5) 0.006(4) 0.002(4) 0.005(4) C14 0.045(5) 0.032(3) 0.026(3) 0.005(2) 0.006(3) 0.001(3) C15 0.054(5) 0.034(3) 0.038(4) 0.008(3) 0.012(4) -0.011(3) N1 0.047(5) 0.038(3) 0.030(3) 0.009(2) 0.012(3) -0.002(3) C11 0.050(5) 0.040(5) 0.025(4) 0.004(4) 0.014(4) 0.007(4) C12 0.027(5) 0.030(4) 0.023(4) 0.006(3) -0.001(3) -0.002(3) C13' 0.028(7) 0.028(7) 0.022(7) 0.011(7) 0.003(6) -0.001(7) C14' 0.049(7) 0.027(5) 0.025(5) 0.006(4) 0.013(5) 0.000(5) C15' 0.052(7) 0.028(5) 0.033(6) 0.000(4) 0.005(5) -0.003(5) N1' 0.055(7) 0.037(5) 0.032(5) 0.005(4) 0.011(5) -0.008(5) C11' 0.045(7) 0.031(7) 0.035(7) 0.010(7) 0.006(7) 0.001(7) C12' 0.039(7) 0.025(6) 0.031(6) 0.009(5) 0.006(5) 0.009(5) 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 C13 126.0(5) . . ? C2 C1 C13' 129.1(8) . . ? C2 C1 P1 110.6(2) . . ? C13 C1 P1 123.5(5) . . ? C13' C1 P1 120.2(8) . . ? C1 C2 C20 124.6(2) . . ? C1 C2 C3 113.8(2) . . ? C20 C2 C3 121.7(2) . . ? C8 C3 C4 119.3(2) . . ? C8 C3 C2 126.7(2) . . ? C4 C3 C2 113.8(2) . . ? C5 C4 C3 121.3(2) . . ? C5 C4 P1 129.8(2) . . ? C3 C4 P1 108.74(18) . . ? C4 C5 C6 119.0(2) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C7 C6 C5 120.2(3) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 121.3(3) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C3 C8 C7 118.9(2) . . ? C3 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? C22 C17 C18 118.9(2) . . ? C22 C17 N2 121.1(2) . . ? C18 C17 N2 119.9(2) . . ? C19 C18 C17 120.1(2) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 121.0(2) . . ? C18 C19 H19 119.5 . . ? C20 C19 H19 119.5 . . ? C19 C20 C21 118.5(2) . . ? C19 C20 C2 120.8(2) . . ? C21 C20 C2 120.6(2) . . ? C22 C21 C20 120.2(2) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C17 C22 C21 121.2(2) . . ? C17 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C28 C23 C24 119.0(2) . . ? C28 C23 N2 120.4(2) . . ? C24 C23 N2 120.7(2) . . ? C25 C24 C23 119.9(3) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C26 C25 C24 120.6(3) . . ? C26 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C27 C26 C25 119.4(3) . . ? C27 C26 H26 120.3 . . ? C25 C26 H26 120.3 . . ? C28 C27 C26 120.3(3) . . ? C28 C27 H27 119.8 . . ? C26 C27 H27 119.8 . . ? C27 C28 C23 120.8(2) . . ? C27 C28 H28 119.6 . . ? C23 C28 H28 119.6 . . ? C34 C29 C30 118.5(2) . . ? C34 C29 N2 121.1(2) . . ? C30 C29 N2 120.4(2) . . ? C31 C30 C29 120.4(3) . . ? C31 C30 H30 119.8 . . ? C29 C30 H30 119.8 . . ? C32 C31 C30 121.0(3) . . ? C32 C31 H31 119.5 . . ? C30 C31 H31 119.5 . . ? C31 C32 C33 118.8(3) . . ? C31 C32 H32 120.6 . . ? C33 C32 H32 120.6 . . ? C32 C33 C34 120.9(3) . . ? C32 C33 H33 119.5 . . ? C34 C33 H33 119.5 . . ? C33 C34 C29 120.4(3) . . ? C33 C34 H34 119.8 . . ? C29 C34 H34 119.8 . . ? C29 N2 C23 121.4(2) . . ? C29 N2 C17 119.8(2) . . ? C23 N2 C17 117.8(2) . . ? O1 P1 O2' 115.9(8) . . ? O1 P1 O2 114.6(2) . . ? O1 P1 C4 118.63(11) . . ? O2' P1 C4 111.8(9) . . ? O2 P1 C4 103.9(2) . . ? O1 P1 C1 117.38(11) . . ? O2' P1 C1 95.8(11) . . ? O2 P1 C1 106.5(3) . . ? C4 P1 C1 92.94(12) . . ? C9 O2 P1 125.9(4) . . ? O2 C9 C10 112.5(5) . . ? O2 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? O2 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? 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 . . ? C9' O2' P1 123.9(17) . . ? O2' C9' C10' 110.8(15) . . ? O2' C9' H9'1 109.5 . . ? C10' C9' H9'1 109.5 . . ? O2' C9' H9'2 109.5 . . ? C10' C9' H9'2 109.5 . . ? H9'1 C9' H9'2 108.1 . . ? C9' C10' H10D 109.5 . . ? C9' C10' H10E 109.5 . . ? H10D C10' H10E 109.5 . . ? C9' C10' H10F 109.5 . . ? H10D C10' H10F 109.5 . . ? H10E C10' H10F 109.5 . . ? C14 C13 C12 116.7(7) . . ? C14 C13 C1 123.2(7) . . ? C12 C13 C1 120.1(7) . . ? C15 C14 C13 119.5(7) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? N1 C15 C14 124.8(7) . . ? N1 C15 H15 117.6 . . ? C14 C15 H15 117.6 . . ? C15 N1 C11 115.1(8) . . ? N1 C11 C12 124.9(10) . . ? N1 C11 H11 117.5 . . ? C12 C11 H11 117.5 . . ? C11 C12 C13 118.8(9) . . ? C11 C12 H12 120.6 . . ? C13 C12 H12 120.6 . . ? C12' C13' C14' 116.7(11) . . ? C12' C13' C1 121.3(11) . . ? C14' C13' C1 121.9(11) . . ? C15' C14' C13' 118.6(11) . . ? C15' C14' H14' 120.7 . . ? C13' C14' H14' 120.7 . . ? N1' C15' C14' 125.0(12) . . ? N1' C15' H15' 117.5 . . ? C14' C15' H15' 117.5 . . ? C15' N1' C11' 116.3(14) . . ? N1' C11' C12' 122.1(16) . . ? N1' C11' H11' 119.0 . . ? C12' C11' H11' 119.0 . . ? C11' C12' C13' 121.0(15) . . ? C11' C12' H12' 119.5 . . ? C13' C12' H12' 119.5 . . ? 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 C1 C2 1.347(3) . ? C1 C13 1.475(7) . ? C1 C13' 1.479(11) . ? C1 P1 1.808(3) . ? C2 C20 1.487(3) . ? C2 C3 1.503(3) . ? C3 C8 1.384(3) . ? C3 C4 1.403(3) . ? C4 C5 1.379(3) . ? C4 P1 1.796(3) . ? C5 C6 1.387(4) . ? C5 H5 0.9500 . ? C6 C7 1.373(4) . ? C6 H6 0.9500 . ? C7 C8 1.399(4) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C17 C22 1.381(3) . ? C17 C18 1.392(3) . ? C17 N2 1.427(3) . ? C18 C19 1.387(3) . ? C18 H18 0.9500 . ? C19 C20 1.394(3) . ? C19 H19 0.9500 . ? C20 C21 1.392(3) . ? C21 C22 1.386(3) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C28 1.383(3) . ? C23 C24 1.387(3) . ? C23 N2 1.422(3) . ? C24 C25 1.380(4) . ? C24 H24 0.9500 . ? C25 C26 1.379(4) . ? C25 H25 0.9500 . ? C26 C27 1.375(4) . ? C26 H26 0.9500 . ? C27 C28 1.372(4) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 C34 1.385(3) . ? C29 C30 1.392(3) . ? C29 N2 1.416(3) . ? C30 C31 1.377(4) . ? C30 H30 0.9500 . ? C31 C32 1.375(4) . ? C31 H31 0.9500 . ? C32 C33 1.375(4) . ? C32 H32 0.9500 . ? C33 C34 1.382(4) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? O1 P1 1.4687(17) . ? P1 O2' 1.568(16) . ? P1 O2 1.575(4) . ? O2 C9 1.437(5) . ? C9 C10 1.493(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? O2' C9' 1.434(17) . ? C9' C10' 1.518(16) . ? C9' H9'1 0.9900 . ? C9' H9'2 0.9900 . ? C10' H10D 0.9800 . ? C10' H10E 0.9800 . ? C10' H10F 0.9800 . ? C13 C14 1.390(8) . ? C13 C12 1.398(8) . ? C14 C15 1.378(7) . ? C14 H14 0.9500 . ? C15 N1 1.331(8) . ? C15 H15 0.9500 . ? N1 C11 1.341(10) . ? C11 C12 1.381(8) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13' C12' 1.387(12) . ? C13' C14' 1.388(12) . ? C14' C15' 1.385(11) . ? C14' H14' 0.9500 . ? C15' N1' 1.330(11) . ? C15' H15' 0.9500 . ? N1' C11' 1.345(13) . ? C11' C12' 1.384(12) . ? C11' H11' 0.9500 . ? C12' H12' 0.9500 . ?