#------------------------------------------------------------------------------ #$Date: 2021-09-06 15:32:05 +0300 (Mon, 06 Sep 2021) $ #$Revision: 268948 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158188.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_7158188 loop_ _publ_author_name 'Tajti, \'Ad\'am' 'Szab\'o, K\'armen Em\>oke' 'Popovics-T\'oth, N\'ora' 'Iskanderov, Javad' 'Perdih, Franc' 'Hackler, L\'aszl\'o' 'Kari, Be\'ata' 'Pusk\'as, L\'aszl\'o G' 'B\'alint, Erika' _publ_section_title ; PMDTA-catalyzed multicomponent synthesis and biological activity of 2-amino-4H-chromenes containing a phosphonate or phosphine oxide moiety. ; _journal_issue 31 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 6883 _journal_page_last 6891 _journal_paper_doi 10.1039/d1ob01204e _journal_volume 19 _journal_year 2021 _chemical_formula_moiety 'C26 H25 N2 O2 P' _chemical_formula_sum 'C26 H25 N2 O2 P' _chemical_formula_weight 428.45 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-05-13 deposited with the CCDC. 2021-07-22 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.224(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.9952(5) _cell_length_b 11.0767(5) _cell_length_c 15.1578(6) _cell_measurement_reflns_used 4046 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 30.1230 _cell_measurement_theta_min 3.1640 _cell_volume 2178.42(16) _computing_cell_refinement 'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 150(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.4933 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, Atlas' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_unetI/netI 0.0398 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 11113 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.484 _diffrn_reflns_theta_min 2.418 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.152 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.80050 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.306 _exptl_crystal_description prism _exptl_crystal_F_000 904 _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _refine_diff_density_max 0.359 _refine_diff_density_min -0.397 _refine_diff_density_rms 0.051 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 290 _refine_ls_number_reflns 4993 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.019 _refine_ls_R_factor_all 0.0553 _refine_ls_R_factor_gt 0.0416 _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^)+(0.0498P)^2^+1.0008P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1038 _refine_ls_wR_factor_ref 0.1128 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4000 _reflns_number_total 4993 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01204e2.cif _cod_data_source_block Structure-14c _cod_depositor_comments 'Adding full bibliography for 7158185--7158189.cif.' _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7158188 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.928 _shelx_estimated_absorpt_t_max 0.970 _shelx_res_file ; TITL mob720.res in P2(1)/c mob720.res created by SHELXL-2018/3 at 10:05:15 on 13-Aug-2019 CELL 0.71073 12.9952 11.0767 15.1578 90 93.224 90 ZERR 4 0.0005 0.0005 0.0006 0 0.004 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O P UNIT 104 100 8 8 4 EQIV $1 +X,1.5-Y,0.5+Z EQIV $2 -X,1-Y,1-Z L.S. 10 PLAN 20 SIZE 0.5 0.2 0.2 TEMP -123 HTAB N2 O1_$1 HTAB N2 N1_$2 BOND $H CONF fmap 2 acta SHEL 20.4 0.77 REM REM REM WGHT 0.049800 1.000800 FVAR 0.44374 P1 5 0.249530 0.786827 0.298445 11.00000 0.01681 0.01879 = 0.01790 0.00080 -0.00040 -0.00142 O1 4 0.278384 0.901737 0.254802 11.00000 0.02581 0.02192 = 0.02076 0.00363 -0.00015 -0.00389 O2 4 0.302596 0.723088 0.559128 11.00000 0.02178 0.02234 = 0.02393 0.00369 -0.00339 -0.00495 N1 3 -0.010175 0.597689 0.413875 11.00000 0.02838 0.03581 = 0.04280 0.01111 -0.00782 -0.01158 N2 3 0.200074 0.565237 0.573042 11.00000 0.02331 0.02156 = 0.02332 0.00380 -0.00079 -0.00452 H2A 2 0.226253 0.567395 0.628147 11.00000 -1.20000 H2B 2 0.141451 0.527113 0.563598 11.00000 -1.20000 C1 1 0.191749 0.818746 0.404834 11.00000 0.01757 0.01657 = 0.02032 0.00034 0.00113 -0.00014 AFIX 13 H1 2 0.129033 0.869280 0.391474 11.00000 -1.20000 AFIX 0 C2 1 0.158266 0.709578 0.455827 11.00000 0.01767 0.01835 = 0.02148 -0.00017 0.00165 -0.00278 C3 1 0.215347 0.666551 0.526986 11.00000 0.01696 0.01799 = 0.02134 -0.00171 0.00325 -0.00185 C4 1 0.318323 0.842272 0.534457 11.00000 0.01972 0.01918 = 0.02158 -0.00100 0.00476 -0.00382 C5 1 0.266074 0.893665 0.461688 11.00000 0.01907 0.01906 = 0.02169 -0.00325 0.00448 -0.00049 C6 1 0.388871 0.906460 0.587604 11.00000 0.02530 0.03165 = 0.02187 -0.00287 0.00110 -0.00689 AFIX 43 H6 2 0.423882 0.868826 0.636974 11.00000 -1.20000 AFIX 0 C7 1 0.407784 1.025514 0.568150 11.00000 0.02993 0.03114 = 0.03267 -0.01101 0.00440 -0.01263 AFIX 43 H7 2 0.456290 1.070472 0.604027 11.00000 -1.20000 AFIX 0 C8 1 0.356098 1.079676 0.496299 11.00000 0.03549 0.02019 = 0.03920 -0.00456 0.00922 -0.00700 AFIX 43 H8 2 0.368603 1.162138 0.483403 11.00000 -1.20000 AFIX 0 C9 1 0.286473 1.014452 0.443294 11.00000 0.02699 0.01894 = 0.02934 0.00037 0.00453 0.00035 AFIX 43 H9 2 0.252036 1.052234 0.393708 11.00000 -1.20000 AFIX 0 C10 1 0.065040 0.648571 0.431468 11.00000 0.02356 0.02212 = 0.02478 0.00476 -0.00007 -0.00125 C11 1 0.357985 0.689204 0.321803 11.00000 0.01863 0.02159 = 0.01777 -0.00351 -0.00138 0.00165 C12 1 0.455331 0.731008 0.301046 11.00000 0.02192 0.02467 = 0.01931 -0.00319 -0.00060 -0.00271 AFIX 43 H12 2 0.462033 0.809010 0.275952 11.00000 -1.20000 AFIX 0 C13 1 0.542316 0.659457 0.316806 11.00000 0.02066 0.03429 = 0.02582 -0.00771 -0.00021 -0.00030 C14 1 0.530239 0.545231 0.352938 11.00000 0.02333 0.03201 = 0.03199 -0.00513 -0.00347 0.00797 AFIX 43 H14 2 0.589110 0.495068 0.362480 11.00000 -1.20000 AFIX 0 C15 1 0.434817 0.502197 0.375507 11.00000 0.02901 0.02442 = 0.02391 -0.00336 -0.00166 0.00418 C16 1 0.348653 0.575091 0.359511 11.00000 0.02201 0.02344 = 0.02132 -0.00305 0.00113 -0.00039 AFIX 43 H16 2 0.282796 0.546917 0.374401 11.00000 -1.20000 AFIX 0 C17 1 0.648341 0.702549 0.295408 11.00000 0.02180 0.04767 = 0.04810 -0.00515 0.00463 0.00026 AFIX 137 H17A 2 0.673896 0.653173 0.247653 11.00000 -1.50000 H17B 2 0.695330 0.695242 0.348010 11.00000 -1.50000 H17C 2 0.644585 0.787189 0.276676 11.00000 -1.50000 AFIX 0 C18 1 0.424407 0.379739 0.417205 11.00000 0.04082 0.02547 = 0.03734 0.00293 -0.00126 0.00717 AFIX 137 H18A 2 0.363305 0.378649 0.452258 11.00000 -1.50000 H18B 2 0.485861 0.362724 0.455641 11.00000 -1.50000 H18C 2 0.417279 0.318142 0.370853 11.00000 -1.50000 AFIX 0 C19 1 0.151339 0.706187 0.233747 11.00000 0.01953 0.02341 = 0.01855 0.00128 -0.00022 -0.00375 C20 1 0.062250 0.771130 0.208269 11.00000 0.02183 0.02453 = 0.02325 0.00058 -0.00025 -0.00282 AFIX 43 H20 2 0.054943 0.851866 0.228119 11.00000 -1.20000 AFIX 0 C21 1 -0.015429 0.719498 0.154558 11.00000 0.02027 0.03155 = 0.02560 0.00494 -0.00092 -0.00337 C22 1 -0.002395 0.600733 0.126557 11.00000 0.02256 0.03183 = 0.02431 0.00000 -0.00255 -0.01005 AFIX 43 H22 2 -0.055610 0.564239 0.090198 11.00000 -1.20000 AFIX 0 C23 1 0.085182 0.533976 0.149744 11.00000 0.02542 0.02622 = 0.02123 -0.00108 0.00512 -0.00632 C24 1 0.162394 0.588395 0.204147 11.00000 0.02023 0.02393 = 0.02150 0.00046 0.00123 -0.00207 AFIX 43 H24 2 0.223060 0.544344 0.221045 11.00000 -1.20000 AFIX 0 C25 1 -0.111134 0.790302 0.127207 11.00000 0.02495 0.03780 = 0.04338 0.00264 -0.00977 -0.00066 AFIX 137 H25A 2 -0.168530 0.762772 0.161340 11.00000 -1.50000 H25B 2 -0.128282 0.777767 0.064085 11.00000 -1.50000 H25C 2 -0.098764 0.876362 0.138428 11.00000 -1.50000 AFIX 0 C26 1 0.100132 0.407203 0.117531 11.00000 0.03008 0.03144 = 0.03175 -0.00813 0.00335 -0.00702 AFIX 137 H26A 2 0.168397 0.399893 0.093674 11.00000 -1.50000 H26B 2 0.047004 0.388375 0.071122 11.00000 -1.50000 H26C 2 0.094744 0.350676 0.166794 11.00000 -1.50000 AFIX 0 HKLF 4 REM mob720.res in P2(1)/c REM wR2 = 0.1128, GooF = S = 1.019, Restrained GooF = 1.019 for all data REM R1 = 0.0416 for 4000 Fo > 4sig(Fo) and 0.0553 for all 4993 data REM 290 parameters refined using 0 restraints END WGHT 0.0498 1.0007 REM Highest difference peak 0.359, deepest hole -0.397, 1-sigma level 0.051 Q1 1 0.1997 0.7368 0.2623 11.00000 0.05 0.36 Q2 1 0.3026 0.7276 0.3119 11.00000 0.05 0.35 Q3 1 0.4760 0.3196 0.3983 11.00000 0.05 0.26 Q4 1 0.2295 0.8566 0.4329 11.00000 0.05 0.26 Q5 1 0.0560 0.5852 0.1247 11.00000 0.05 0.26 Q6 1 0.1256 0.5556 0.1783 11.00000 0.05 0.25 Q7 1 0.3652 0.8674 0.5495 11.00000 0.05 0.25 Q8 1 0.1697 0.7040 0.5045 11.00000 0.05 0.25 Q9 1 0.3961 0.5460 0.3671 11.00000 0.05 0.24 Q10 1 0.5951 0.6821 0.3049 11.00000 0.05 0.24 Q11 1 0.2171 0.8088 0.3648 11.00000 0.05 0.24 Q12 1 0.1788 0.7578 0.4250 11.00000 0.05 0.22 Q13 1 0.0858 0.4741 0.1329 11.00000 0.05 0.22 Q14 1 0.1635 0.3748 0.1435 11.00000 0.05 0.22 Q15 1 0.4011 0.6999 0.3003 11.00000 0.05 0.22 Q16 1 0.3109 0.8581 0.4816 11.00000 0.05 0.22 Q17 1 0.3035 1.0583 0.4826 11.00000 0.05 0.22 Q18 1 0.1234 0.6752 0.4399 11.00000 0.05 0.22 Q19 1 0.2988 0.8389 0.2704 11.00000 0.05 0.21 Q20 1 0.0411 0.7518 0.1550 11.00000 0.05 0.21 ; _shelx_res_checksum 85057 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.24953(3) 0.78683(4) 0.29845(3) 0.01789(11) Uani 1 1 d . . . . . O1 O 0.27838(9) 0.90174(10) 0.25480(7) 0.0229(3) Uani 1 1 d . . . . . O2 O 0.30260(8) 0.72309(10) 0.55913(7) 0.0229(3) Uani 1 1 d . . . . . N1 N -0.01017(12) 0.59769(15) 0.41388(11) 0.0360(4) Uani 1 1 d . . . . . N2 N 0.20007(11) 0.56524(13) 0.57304(10) 0.0228(3) Uani 1 1 d . . . . . H2A H 0.2263(15) 0.5674(18) 0.6281(14) 0.027 Uiso 1 1 d . U . . . H2B H 0.1415(15) 0.5271(18) 0.5636(13) 0.027 Uiso 1 1 d . U . . . C1 C 0.19175(12) 0.81875(14) 0.40483(10) 0.0182(3) Uani 1 1 d . . . . . H1 H 0.129033 0.869280 0.391474 0.022 Uiso 1 1 calc R U . . . C2 C 0.15827(11) 0.70958(14) 0.45583(10) 0.0191(3) Uani 1 1 d . . . . . C3 C 0.21535(11) 0.66655(14) 0.52699(10) 0.0187(3) Uani 1 1 d . . . . . C4 C 0.31832(12) 0.84227(14) 0.53446(10) 0.0200(3) Uani 1 1 d . . . . . C5 C 0.26607(12) 0.89367(14) 0.46169(10) 0.0198(3) Uani 1 1 d . . . . . C6 C 0.38887(13) 0.90646(16) 0.58760(11) 0.0263(4) Uani 1 1 d . . . . . H6 H 0.423882 0.868826 0.636974 0.032 Uiso 1 1 calc R U . . . C7 C 0.40778(14) 1.02551(17) 0.56815(12) 0.0311(4) Uani 1 1 d . . . . . H7 H 0.456290 1.070472 0.604027 0.037 Uiso 1 1 calc R U . . . C8 C 0.35610(14) 1.07968(16) 0.49630(13) 0.0314(4) Uani 1 1 d . . . . . H8 H 0.368603 1.162138 0.483403 0.038 Uiso 1 1 calc R U . . . C9 C 0.28647(13) 1.01445(15) 0.44329(12) 0.0250(4) Uani 1 1 d . . . . . H9 H 0.252036 1.052234 0.393708 0.030 Uiso 1 1 calc R U . . . C10 C 0.06504(13) 0.64857(15) 0.43147(11) 0.0235(3) Uani 1 1 d . . . . . C11 C 0.35799(12) 0.68920(14) 0.32180(10) 0.0194(3) Uani 1 1 d . . . . . C12 C 0.45533(12) 0.73101(15) 0.30105(11) 0.0220(3) Uani 1 1 d . . . . . H12 H 0.462033 0.809010 0.275952 0.026 Uiso 1 1 calc R U . . . C13 C 0.54232(13) 0.65946(17) 0.31681(11) 0.0270(4) Uani 1 1 d . . . . . C14 C 0.53024(13) 0.54523(17) 0.35294(12) 0.0293(4) Uani 1 1 d . . . . . H14 H 0.589110 0.495068 0.362480 0.035 Uiso 1 1 calc R U . . . C15 C 0.43482(13) 0.50220(16) 0.37551(11) 0.0259(4) Uani 1 1 d . . . . . C16 C 0.34865(12) 0.57509(15) 0.35951(11) 0.0223(3) Uani 1 1 d . . . . . H16 H 0.282796 0.546917 0.374401 0.027 Uiso 1 1 calc R U . . . C17 C 0.64834(14) 0.7025(2) 0.29541(15) 0.0391(5) Uani 1 1 d . . . . . H17A H 0.673896 0.653173 0.247653 0.059 Uiso 1 1 calc R U . . . H17B H 0.695330 0.695242 0.348010 0.059 Uiso 1 1 calc R U . . . H17C H 0.644585 0.787189 0.276676 0.059 Uiso 1 1 calc R U . . . C18 C 0.42441(16) 0.37974(17) 0.41720(13) 0.0347(4) Uani 1 1 d . . . . . H18A H 0.363305 0.378649 0.452258 0.052 Uiso 1 1 calc R U . . . H18B H 0.485861 0.362724 0.455641 0.052 Uiso 1 1 calc R U . . . H18C H 0.417279 0.318142 0.370853 0.052 Uiso 1 1 calc R U . . . C19 C 0.15134(12) 0.70619(15) 0.23375(10) 0.0205(3) Uani 1 1 d . . . . . C20 C 0.06225(12) 0.77113(15) 0.20827(11) 0.0233(3) Uani 1 1 d . . . . . H20 H 0.054943 0.851866 0.228119 0.028 Uiso 1 1 calc R U . . . C21 C -0.01543(12) 0.71950(16) 0.15456(12) 0.0259(4) Uani 1 1 d . . . . . C22 C -0.00240(13) 0.60073(16) 0.12656(11) 0.0264(4) Uani 1 1 d . . . . . H22 H -0.055610 0.564239 0.090198 0.032 Uiso 1 1 calc R U . . . C23 C 0.08518(13) 0.53398(16) 0.14974(11) 0.0241(4) Uani 1 1 d . . . . . C24 C 0.16239(12) 0.58840(15) 0.20415(11) 0.0219(3) Uani 1 1 d . . . . . H24 H 0.223060 0.544344 0.221045 0.026 Uiso 1 1 calc R U . . . C25 C -0.11113(14) 0.79030(18) 0.12721(14) 0.0358(4) Uani 1 1 d . . . . . H25A H -0.168530 0.762772 0.161340 0.054 Uiso 1 1 calc R U . . . H25B H -0.128282 0.777767 0.064085 0.054 Uiso 1 1 calc R U . . . H25C H -0.098764 0.876362 0.138428 0.054 Uiso 1 1 calc R U . . . C26 C 0.10013(14) 0.40720(17) 0.11753(13) 0.0310(4) Uani 1 1 d . . . . . H26A H 0.168397 0.399893 0.093674 0.047 Uiso 1 1 calc R U . . . H26B H 0.047004 0.388375 0.071122 0.047 Uiso 1 1 calc R U . . . H26C H 0.094744 0.350676 0.166794 0.047 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 P1 0.0168(2) 0.0188(2) 0.0179(2) 0.00080(16) -0.00040(15) -0.00142(15) O1 0.0258(6) 0.0219(6) 0.0208(6) 0.0036(5) -0.0001(5) -0.0039(5) O2 0.0218(6) 0.0223(6) 0.0239(6) 0.0037(5) -0.0034(5) -0.0050(5) N1 0.0284(8) 0.0358(9) 0.0428(9) 0.0111(8) -0.0078(7) -0.0116(7) N2 0.0233(7) 0.0216(7) 0.0233(7) 0.0038(6) -0.0008(6) -0.0045(6) C1 0.0176(7) 0.0166(7) 0.0203(8) 0.0003(6) 0.0011(6) -0.0001(6) C2 0.0177(7) 0.0183(7) 0.0215(8) -0.0002(6) 0.0017(6) -0.0028(6) C3 0.0170(7) 0.0180(7) 0.0213(8) -0.0017(6) 0.0033(6) -0.0019(6) C4 0.0197(7) 0.0192(8) 0.0216(8) -0.0010(6) 0.0048(6) -0.0038(6) C5 0.0191(7) 0.0191(8) 0.0217(8) -0.0032(6) 0.0045(6) -0.0005(6) C6 0.0253(8) 0.0316(9) 0.0219(8) -0.0029(7) 0.0011(7) -0.0069(7) C7 0.0299(9) 0.0311(10) 0.0327(10) -0.0110(8) 0.0044(8) -0.0126(8) C8 0.0355(10) 0.0202(8) 0.0392(10) -0.0046(8) 0.0092(8) -0.0070(7) C9 0.0270(8) 0.0189(8) 0.0293(9) 0.0004(7) 0.0045(7) 0.0003(7) C10 0.0236(8) 0.0221(8) 0.0248(8) 0.0048(7) -0.0001(7) -0.0013(7) C11 0.0186(7) 0.0216(8) 0.0178(7) -0.0035(6) -0.0014(6) 0.0017(6) C12 0.0219(8) 0.0247(8) 0.0193(8) -0.0032(7) -0.0006(6) -0.0027(7) C13 0.0207(8) 0.0343(10) 0.0258(8) -0.0077(8) -0.0002(7) -0.0003(7) C14 0.0233(8) 0.0320(10) 0.0320(9) -0.0051(8) -0.0035(7) 0.0080(7) C15 0.0290(9) 0.0244(9) 0.0239(8) -0.0034(7) -0.0017(7) 0.0042(7) C16 0.0220(8) 0.0234(8) 0.0213(8) -0.0030(7) 0.0011(6) -0.0004(7) C17 0.0218(9) 0.0477(12) 0.0481(12) -0.0052(10) 0.0046(8) 0.0003(8) C18 0.0408(11) 0.0255(9) 0.0373(10) 0.0029(8) -0.0013(9) 0.0072(8) C19 0.0195(7) 0.0234(8) 0.0186(7) 0.0013(6) -0.0002(6) -0.0037(6) C20 0.0218(8) 0.0245(8) 0.0232(8) 0.0006(7) -0.0002(6) -0.0028(7) C21 0.0203(8) 0.0315(9) 0.0256(8) 0.0049(7) -0.0009(7) -0.0034(7) C22 0.0226(8) 0.0318(9) 0.0243(8) 0.0000(7) -0.0026(7) -0.0101(7) C23 0.0254(8) 0.0262(9) 0.0212(8) -0.0011(7) 0.0051(7) -0.0063(7) C24 0.0202(7) 0.0239(8) 0.0215(8) 0.0005(7) 0.0012(6) -0.0021(6) C25 0.0250(9) 0.0378(11) 0.0434(11) 0.0026(9) -0.0098(8) -0.0007(8) C26 0.0301(9) 0.0314(10) 0.0318(9) -0.0081(8) 0.0034(8) -0.0070(8) 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 O1 P1 C11 112.77(7) . . ? O1 P1 C19 111.68(7) . . ? C11 P1 C19 109.43(8) . . ? O1 P1 C1 110.35(7) . . ? C11 P1 C1 107.19(7) . . ? C19 P1 C1 105.03(7) . . ? C3 O2 C4 118.21(12) . . ? C3 N2 H2A 114.1(13) . . ? C3 N2 H2B 118.1(13) . . ? H2A N2 H2B 116.9(18) . . ? C5 C1 C2 109.98(13) . . ? C5 C1 P1 108.97(10) . . ? C2 C1 P1 115.79(11) . . ? C5 C1 H1 107.2 . . ? C2 C1 H1 107.2 . . ? P1 C1 H1 107.2 . . ? C3 C2 C10 117.34(14) . . ? C3 C2 C1 121.71(14) . . ? C10 C2 C1 120.94(14) . . ? N2 C3 C2 127.97(15) . . ? N2 C3 O2 110.06(14) . . ? C2 C3 O2 121.91(14) . . ? C6 C4 C5 122.14(15) . . ? C6 C4 O2 115.74(15) . . ? C5 C4 O2 122.12(14) . . ? C4 C5 C9 117.60(15) . . ? C4 C5 C1 119.93(14) . . ? C9 C5 C1 122.46(15) . . ? C7 C6 C4 119.23(17) . . ? C7 C6 H6 120.4 . . ? C4 C6 H6 120.4 . . ? C6 C7 C8 119.96(17) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C9 C8 C7 120.30(17) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C5 120.76(17) . . ? C8 C9 H9 119.6 . . ? C5 C9 H9 119.6 . . ? N1 C10 C2 178.19(19) . . ? C16 C11 C12 119.49(15) . . ? C16 C11 P1 122.75(12) . . ? C12 C11 P1 117.76(12) . . ? C13 C12 C11 120.62(16) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 118.52(15) . . ? C12 C13 C17 121.71(17) . . ? C14 C13 C17 119.76(16) . . ? C15 C14 C13 122.08(16) . . ? C15 C14 H14 119.0 . . ? C13 C14 H14 119.0 . . ? C14 C15 C16 118.62(16) . . ? C14 C15 C18 121.00(16) . . ? C16 C15 C18 120.38(16) . . ? C15 C16 C11 120.64(15) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C24 C19 C20 119.51(15) . . ? C24 C19 P1 123.93(12) . . ? C20 C19 P1 116.43(12) . . ? C21 C20 C19 120.98(16) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C20 C21 C22 118.12(16) . . ? C20 C21 C25 120.63(16) . . ? C22 C21 C25 121.25(16) . . ? C23 C22 C21 122.54(16) . . ? C23 C22 H22 118.7 . . ? C21 C22 H22 118.7 . . ? C22 C23 C24 118.11(16) . . ? C22 C23 C26 122.38(16) . . ? C24 C23 C26 119.51(16) . . ? C19 C24 C23 120.73(15) . . ? C19 C24 H24 119.6 . . ? C23 C24 H24 119.6 . . ? C21 C25 H25A 109.5 . . ? C21 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C21 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.4921(12) . ? P1 C11 1.7958(16) . ? P1 C19 1.8020(16) . ? P1 C1 1.8508(15) . ? O2 C3 1.3612(18) . ? O2 C4 1.3903(19) . ? N1 C10 1.147(2) . ? N2 C3 1.342(2) . ? N2 H2A 0.88(2) . ? N2 H2B 0.88(2) . ? C1 C5 1.507(2) . ? C1 C2 1.512(2) . ? C1 H1 1.0000 . ? C2 C3 1.360(2) . ? C2 C10 1.418(2) . ? C4 C6 1.383(2) . ? C4 C5 1.385(2) . ? C5 C9 1.395(2) . ? C6 C7 1.376(3) . ? C6 H6 0.9500 . ? C7 C8 1.384(3) . ? C7 H7 0.9500 . ? C8 C9 1.380(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C11 C16 1.395(2) . ? C11 C12 1.399(2) . ? C12 C13 1.390(2) . ? C12 H12 0.9500 . ? C13 C14 1.391(3) . ? C13 C17 1.511(2) . ? C14 C15 1.389(2) . ? C14 H14 0.9500 . ? C15 C16 1.391(2) . ? C15 C18 1.506(2) . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C24 1.390(2) . ? C19 C20 1.399(2) . ? C20 C21 1.384(2) . ? C20 H20 0.9500 . ? C21 C22 1.396(2) . ? C21 C25 1.509(2) . ? C22 C23 1.386(2) . ? C22 H22 0.9500 . ? C23 C24 1.399(2) . ? C23 C26 1.503(2) . ? C24 H24 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? 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 _geom_hbond_publ_flag N2 H2A O1 0.88(2) 2.03(2) 2.9060(19) 171.4(18) 4_576 yes N2 H2B N1 0.88(2) 2.24(2) 3.073(2) 159.5(18) 3_566 yes 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 O1 P1 C1 C5 -55.81(12) . . . . ? C11 P1 C1 C5 67.35(12) . . . . ? C19 P1 C1 C5 -176.31(11) . . . . ? O1 P1 C1 C2 179.62(11) . . . . ? C11 P1 C1 C2 -57.22(13) . . . . ? C19 P1 C1 C2 59.12(13) . . . . ? C5 C1 C2 C3 -21.6(2) . . . . ? P1 C1 C2 C3 102.47(16) . . . . ? C5 C1 C2 C10 157.84(14) . . . . ? P1 C1 C2 C10 -78.11(17) . . . . ? C10 C2 C3 N2 7.2(2) . . . . ? C1 C2 C3 N2 -173.39(15) . . . . ? C10 C2 C3 O2 -175.77(14) . . . . ? C1 C2 C3 O2 3.7(2) . . . . ? C4 O2 C3 N2 -165.08(13) . . . . ? C4 O2 C3 C2 17.4(2) . . . . ? C3 O2 C4 C6 161.20(14) . . . . ? C3 O2 C4 C5 -18.3(2) . . . . ? C6 C4 C5 C9 -0.3(2) . . . . ? O2 C4 C5 C9 179.17(14) . . . . ? C6 C4 C5 C1 178.63(14) . . . . ? O2 C4 C5 C1 -1.9(2) . . . . ? C2 C1 C5 C4 20.27(19) . . . . ? P1 C1 C5 C4 -107.65(14) . . . . ? C2 C1 C5 C9 -160.83(14) . . . . ? P1 C1 C5 C9 71.26(17) . . . . ? C5 C4 C6 C7 0.3(2) . . . . ? O2 C4 C6 C7 -179.22(14) . . . . ? C4 C6 C7 C8 0.3(3) . . . . ? C6 C7 C8 C9 -0.8(3) . . . . ? C7 C8 C9 C5 0.8(3) . . . . ? C4 C5 C9 C8 -0.2(2) . . . . ? C1 C5 C9 C8 -179.14(15) . . . . ? O1 P1 C11 C16 -177.61(12) . . . . ? C19 P1 C11 C16 -52.64(15) . . . . ? C1 P1 C11 C16 60.75(15) . . . . ? O1 P1 C11 C12 2.55(15) . . . . ? C19 P1 C11 C12 127.51(13) . . . . ? C1 P1 C11 C12 -119.10(13) . . . . ? C16 C11 C12 C13 0.7(2) . . . . ? P1 C11 C12 C13 -179.47(12) . . . . ? C11 C12 C13 C14 0.5(2) . . . . ? C11 C12 C13 C17 -179.73(16) . . . . ? C12 C13 C14 C15 -1.6(3) . . . . ? C17 C13 C14 C15 178.65(17) . . . . ? C13 C14 C15 C16 1.4(3) . . . . ? C13 C14 C15 C18 -178.03(17) . . . . ? C14 C15 C16 C11 -0.2(2) . . . . ? C18 C15 C16 C11 179.28(16) . . . . ? C12 C11 C16 C15 -0.8(2) . . . . ? P1 C11 C16 C15 179.31(13) . . . . ? O1 P1 C19 C24 122.86(14) . . . . ? C11 P1 C19 C24 -2.73(16) . . . . ? C1 P1 C19 C24 -117.52(14) . . . . ? O1 P1 C19 C20 -53.00(14) . . . . ? C11 P1 C19 C20 -178.59(12) . . . . ? C1 P1 C19 C20 66.62(14) . . . . ? C24 C19 C20 C21 0.5(2) . . . . ? P1 C19 C20 C21 176.55(13) . . . . ? C19 C20 C21 C22 0.0(2) . . . . ? C19 C20 C21 C25 -179.84(16) . . . . ? C20 C21 C22 C23 -0.7(3) . . . . ? C25 C21 C22 C23 179.21(16) . . . . ? C21 C22 C23 C24 0.7(2) . . . . ? C21 C22 C23 C26 -178.37(16) . . . . ? C20 C19 C24 C23 -0.4(2) . . . . ? P1 C19 C24 C23 -176.18(12) . . . . ? C22 C23 C24 C19 -0.2(2) . . . . ? C26 C23 C24 C19 178.97(15) . . . . ?