#------------------------------------------------------------------------------ #$Date: 2021-09-06 15:32:05 +0300 (Mon, 06 Sep 2021) $ #$Revision: 268948 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158185.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_7158185 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 'C18 H25 N2 O4 P' _chemical_formula_sum 'C18 H25 N2 O4 P' _chemical_formula_weight 364.37 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 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 109.314(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.4732(3) _cell_length_b 8.9061(2) _cell_length_c 15.9214(4) _cell_measurement_reflns_used 4054 _cell_measurement_temperature 150.00(10) _cell_measurement_theta_max 74.6260 _cell_measurement_theta_min 3.5510 _cell_volume 1936.76(8) _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-2018/3 (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 150.00(10) _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 0.999 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0338 _diffrn_reflns_av_unetI/netI 0.0320 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 7323 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 70.035 _diffrn_reflns_theta_min 3.582 _diffrn_source 'micro-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 1.462 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.37774 _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 'light yellow' _exptl_crystal_density_diffrn 1.250 _exptl_crystal_description prism _exptl_crystal_F_000 776 _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.500 _exptl_crystal_size_min 0.200 _refine_diff_density_max 0.525 _refine_diff_density_min -0.721 _refine_diff_density_rms 0.093 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 234 _refine_ls_number_reflns 3670 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.075 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0534 _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^)+(0.0886P)^2^+0.6388P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1380 _refine_ls_wR_factor_ref 0.1431 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3295 _reflns_number_total 3670 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01204e2.cif _cod_data_source_block Structure-2c _cod_depositor_comments 'Adding full bibliography for 7158185--7158189.cif.' _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7158185 _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 0.529 _shelx_estimated_absorpt_t_max 0.759 _shelx_res_file ; TITL cu174.res in P2(1)/n cu174.res created by SHELXL-2018/3 at 16:09:24 on 08-Jul-2020 CELL 1.54184 14.4732 8.9061 15.9214 90 109.314 90 ZERR 4 0.0003 0.0002 0.0004 0 0.002 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O P UNIT 72 100 8 16 4 EQIV $1 1.5-X,0.5+Y,0.5-Z EQIV $2 2-X,1-Y,1-Z DFIX 0.88 N2 H2b DFIX 0.88 N2 H2a L.S. 10 PLAN 20 SIZE 0.2 0.5 0.5 TEMP -123 HTAB N2 O1_$1 HTAB N2 N1_$2 BOND $H CONF fmap 2 acta SHEL 22.1 0.82 REM REM REM WGHT 0.088600 0.638800 FVAR 0.81423 P1 5 0.643018 0.327502 0.397451 11.00000 0.01692 0.02553 = 0.02240 -0.00169 0.00817 -0.00040 O1 4 0.628091 0.310544 0.302268 11.00000 0.02876 0.03577 = 0.02132 -0.00473 0.00773 0.00146 O2 4 0.710192 0.679451 0.295526 11.00000 0.01730 0.03902 = 0.02421 0.00746 0.00707 0.00358 O3 4 0.724912 0.223611 0.460110 11.00000 0.02659 0.03249 = 0.02948 0.00253 0.01127 0.00800 O4 4 0.550895 0.293654 0.426334 11.00000 0.02155 0.02782 = 0.03772 -0.00423 0.01593 -0.00562 N1 3 0.927875 0.482212 0.564725 11.00000 0.02131 0.05236 = 0.03035 0.00687 0.00503 0.00049 N2 3 0.870931 0.648233 0.347507 11.00000 0.01765 0.03954 = 0.02985 0.01098 0.00948 0.00218 H2A 2 0.867567 0.699004 0.297154 11.00000 -1.20000 H2B 2 0.926319 0.608887 0.380791 11.00000 -1.20000 C1 1 0.673620 0.517949 0.437484 11.00000 0.01549 0.02740 = 0.02066 -0.00227 0.00649 -0.00178 AFIX 13 H1 2 0.672796 0.525979 0.499880 11.00000 -1.20000 AFIX 0 C2 1 0.774894 0.555640 0.435552 11.00000 0.01499 0.02752 = 0.02148 0.00101 0.00441 -0.00135 C3 1 0.787301 0.624190 0.362827 11.00000 0.01795 0.02700 = 0.02267 0.00036 0.00516 -0.00034 C4 1 0.621487 0.699425 0.310653 11.00000 0.01580 0.02754 = 0.02603 -0.00300 0.00645 -0.00022 C5 1 0.600164 0.626165 0.378585 11.00000 0.01790 0.02356 = 0.02507 -0.00399 0.00599 -0.00089 C6 1 0.556057 0.796043 0.252437 11.00000 0.02425 0.03122 = 0.03060 0.00255 0.00383 0.00079 AFIX 43 H6 2 0.572860 0.845407 0.206598 11.00000 -1.20000 AFIX 0 C7 1 0.465517 0.819359 0.262341 11.00000 0.02270 0.03041 = 0.04151 0.00105 0.00281 0.00513 AFIX 43 H7 2 0.419270 0.884068 0.222436 11.00000 -1.20000 AFIX 0 C8 1 0.442206 0.748535 0.330314 11.00000 0.02046 0.03565 = 0.04494 -0.00380 0.00987 0.00430 AFIX 43 H8 2 0.380437 0.765955 0.337381 11.00000 -1.20000 AFIX 0 C9 1 0.508786 0.652582 0.387817 11.00000 0.02168 0.03091 = 0.03466 -0.00540 0.01247 -0.00150 AFIX 43 H9 2 0.492246 0.604122 0.434069 11.00000 -1.20000 AFIX 0 C10 1 0.859016 0.514152 0.506557 11.00000 0.01995 0.03077 = 0.02333 0.00124 0.00787 -0.00252 C11 1 0.798653 0.148742 0.430409 11.00000 0.02847 0.04639 = 0.04004 0.00167 0.01650 0.01208 AFIX 23 H11A 2 0.863250 0.197087 0.457838 11.00000 -1.20000 H11B 2 0.780651 0.156490 0.364921 11.00000 -1.20000 AFIX 0 C12 1 0.803651 -0.015222 0.458042 11.00000 0.03259 0.03332 = 0.07570 -0.01666 0.01510 0.00358 AFIX 23 H12A 2 0.738117 -0.060640 0.430575 11.00000 -1.20000 H12B 2 0.849485 -0.068071 0.433791 11.00000 -1.20000 AFIX 0 C13 1 0.835991 -0.041857 0.557383 11.00000 0.04584 0.03441 = 0.08374 0.01883 0.02835 0.00689 AFIX 23 H13A 2 0.831260 -0.150542 0.568361 11.00000 -1.20000 H13B 2 0.790555 0.011274 0.581982 11.00000 -1.20000 AFIX 0 C14 1 0.939729 0.010319 0.606589 11.00000 0.04335 0.08532 = 0.06749 0.02572 0.00958 0.01243 AFIX 137 H14A 2 0.985570 -0.044230 0.584162 11.00000 -1.50000 H14B 2 0.955651 -0.009378 0.670374 11.00000 -1.50000 H14C 2 0.944917 0.118239 0.596987 11.00000 -1.50000 AFIX 0 C15 1 0.502771 0.147894 0.402465 11.00000 0.02497 0.02808 = 0.05103 -0.00073 0.01136 -0.00769 AFIX 23 H15A 2 0.533625 0.073325 0.449502 11.00000 -1.20000 H15B 2 0.509505 0.111905 0.345942 11.00000 -1.20000 AFIX 0 C16 1 0.395804 0.165797 0.392264 11.00000 0.02609 0.04563 = 0.05260 -0.00979 0.01839 -0.01341 AFIX 23 H16A 2 0.390747 0.204258 0.448922 11.00000 -1.20000 H16B 2 0.364260 0.065748 0.381345 11.00000 -1.20000 AFIX 0 C17 1 0.340110 0.270235 0.317802 11.00000 0.02296 0.05025 = 0.09138 0.00099 0.01523 -0.00039 AFIX 23 H17A 2 0.373648 0.368738 0.326287 11.00000 -1.20000 H17B 2 0.273507 0.286279 0.320606 11.00000 -1.20000 AFIX 0 C18 1 0.332051 0.208047 0.225379 11.00000 0.04751 0.10622 = 0.06684 0.02453 0.01721 0.01337 AFIX 137 H18A 2 0.294335 0.278120 0.179321 11.00000 -1.50000 H18B 2 0.298928 0.110462 0.216649 11.00000 -1.50000 H18C 2 0.397763 0.195989 0.221360 11.00000 -1.50000 AFIX 0 HKLF 4 REM cu174.res in P2(1)/n REM wR2 = 0.1431, GooF = S = 1.075, Restrained GooF = 1.075 for all data REM R1 = 0.0534 for 3295 Fo > 4sig(Fo) and 0.0575 for all 3670 data REM 234 parameters refined using 2 restraints END WGHT 0.0886 0.6388 REM Highest difference peak 0.525, deepest hole -0.721, 1-sigma level 0.093 Q1 1 0.3380 0.3123 0.2481 11.00000 0.05 0.53 Q2 1 0.6657 0.3348 0.4884 11.00000 0.05 0.34 Q3 1 0.6560 0.4806 0.3307 11.00000 0.05 0.33 Q4 1 0.5324 0.3389 0.3530 11.00000 0.05 0.32 Q5 1 0.6124 0.3292 0.3320 11.00000 0.05 0.31 Q6 1 0.6407 0.4648 0.2719 11.00000 0.05 0.30 Q7 1 0.7567 0.0058 0.3889 11.00000 0.05 0.29 Q8 1 0.5851 0.3068 0.5100 11.00000 0.05 0.28 Q9 1 0.5442 0.1224 0.4850 11.00000 0.05 0.27 Q10 1 0.7855 -0.0661 0.4985 11.00000 0.05 0.26 Q11 1 0.4965 0.4279 0.3176 11.00000 0.05 0.25 Q12 1 0.6542 0.5072 0.2343 11.00000 0.05 0.23 Q13 1 0.3398 0.7056 0.4162 11.00000 0.05 0.23 Q14 1 0.7712 0.2355 0.5328 11.00000 0.05 0.22 Q15 1 0.6784 0.0862 0.3727 11.00000 0.05 0.22 Q16 1 0.6206 0.3810 0.2082 11.00000 0.05 0.22 Q17 1 0.6371 0.5134 0.3894 11.00000 0.05 0.21 Q18 1 0.5000 0.5000 0.5000 10.50000 0.05 0.21 Q19 1 0.8017 0.0168 0.3233 11.00000 0.05 0.21 Q20 1 0.5240 0.3399 0.2808 11.00000 0.05 0.21 ; _shelx_res_checksum 72896 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 0.64302(3) 0.32750(5) 0.39745(3) 0.02121(17) Uani 1 1 d . . . . . O1 O 0.62809(10) 0.31054(15) 0.30227(8) 0.0288(3) Uani 1 1 d . . . . . O2 O 0.71019(9) 0.67945(14) 0.29553(8) 0.0268(3) Uani 1 1 d . . . . . O3 O 0.72491(9) 0.22361(15) 0.46011(8) 0.0290(3) Uani 1 1 d . . . . . O4 O 0.55089(9) 0.29365(14) 0.42633(9) 0.0275(3) Uani 1 1 d . . . . . N1 N 0.92787(11) 0.4822(2) 0.56472(11) 0.0355(4) Uani 1 1 d . . . . . N2 N 0.87093(11) 0.64823(19) 0.34751(11) 0.0286(4) Uani 1 1 d D . . . . H2A H 0.8676(18) 0.699(2) 0.2972(12) 0.034 Uiso 1 1 d D U . . . H2B H 0.9263(13) 0.609(3) 0.3808(14) 0.034 Uiso 1 1 d D U . . . C1 C 0.67362(11) 0.51795(19) 0.43748(11) 0.0211(4) Uani 1 1 d . . . . . H1 H 0.672796 0.525979 0.499880 0.025 Uiso 1 1 calc R U . . . C2 C 0.77489(12) 0.5556(2) 0.43555(11) 0.0217(4) Uani 1 1 d . . . . . C3 C 0.78730(12) 0.6242(2) 0.36283(11) 0.0229(4) Uani 1 1 d . . . . . C4 C 0.62149(12) 0.6994(2) 0.31065(12) 0.0232(4) Uani 1 1 d . . . . . C5 C 0.60016(12) 0.62616(19) 0.37858(11) 0.0225(4) Uani 1 1 d . . . . . C6 C 0.55606(13) 0.7960(2) 0.25244(13) 0.0300(4) Uani 1 1 d . . . . . H6 H 0.572860 0.845407 0.206598 0.036 Uiso 1 1 calc R U . . . C7 C 0.46552(14) 0.8194(2) 0.26234(15) 0.0335(5) Uani 1 1 d . . . . . H7 H 0.419270 0.884068 0.222436 0.040 Uiso 1 1 calc R U . . . C8 C 0.44221(13) 0.7485(2) 0.33031(14) 0.0339(4) Uani 1 1 d . . . . . H8 H 0.380437 0.765955 0.337381 0.041 Uiso 1 1 calc R U . . . C9 C 0.50879(13) 0.6526(2) 0.38782(13) 0.0283(4) Uani 1 1 d . . . . . H9 H 0.492246 0.604122 0.434069 0.034 Uiso 1 1 calc R U . . . C10 C 0.85902(12) 0.5142(2) 0.50656(12) 0.0245(4) Uani 1 1 d . . . . . C11 C 0.79865(15) 0.1487(3) 0.43041(15) 0.0370(5) Uani 1 1 d . . . . . H11A H 0.863250 0.197087 0.457838 0.044 Uiso 1 1 calc R U . . . H11B H 0.780651 0.156490 0.364921 0.044 Uiso 1 1 calc R U . . . C12 C 0.80365(16) -0.0152(2) 0.45804(18) 0.0479(6) Uani 1 1 d . . . . . H12A H 0.738117 -0.060640 0.430575 0.057 Uiso 1 1 calc R U . . . H12B H 0.849485 -0.068071 0.433791 0.057 Uiso 1 1 calc R U . . . C13 C 0.83599(18) -0.0419(3) 0.5574(2) 0.0529(7) Uani 1 1 d . . . . . H13A H 0.831260 -0.150542 0.568361 0.064 Uiso 1 1 calc R U . . . H13B H 0.790555 0.011274 0.581982 0.064 Uiso 1 1 calc R U . . . C14 C 0.9397(2) 0.0103(4) 0.6066(2) 0.0676(8) Uani 1 1 d . . . . . H14A H 0.985570 -0.044230 0.584162 0.101 Uiso 1 1 calc R U . . . H14B H 0.955651 -0.009378 0.670374 0.101 Uiso 1 1 calc R U . . . H14C H 0.944917 0.118239 0.596987 0.101 Uiso 1 1 calc R U . . . C15 C 0.50277(14) 0.1479(2) 0.40246(16) 0.0350(5) Uani 1 1 d . . . . . H15A H 0.533625 0.073325 0.449502 0.042 Uiso 1 1 calc R U . . . H15B H 0.509505 0.111905 0.345942 0.042 Uiso 1 1 calc R U . . . C16 C 0.39580(15) 0.1658(3) 0.39226(16) 0.0401(5) Uani 1 1 d . . . . . H16A H 0.390747 0.204258 0.448922 0.048 Uiso 1 1 calc R U . . . H16B H 0.364260 0.065748 0.381345 0.048 Uiso 1 1 calc R U . . . C17 C 0.34011(16) 0.2702(3) 0.3178(2) 0.0558(7) Uani 1 1 d . . . . . H17A H 0.373648 0.368738 0.326287 0.067 Uiso 1 1 calc R U . . . H17B H 0.273507 0.286279 0.320606 0.067 Uiso 1 1 calc R U . . . C18 C 0.3321(2) 0.2080(5) 0.2254(2) 0.0739(9) Uani 1 1 d . . . . . H18A H 0.294335 0.278120 0.179321 0.111 Uiso 1 1 calc R U . . . H18B H 0.298928 0.110462 0.216649 0.111 Uiso 1 1 calc R U . . . H18C H 0.397763 0.195989 0.221360 0.111 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 0.0169(2) 0.0255(3) 0.0224(3) -0.00169(15) 0.00817(18) -0.00040(14) O1 0.0288(7) 0.0358(7) 0.0213(7) -0.0047(5) 0.0077(5) 0.0015(5) O2 0.0173(6) 0.0390(7) 0.0242(7) 0.0075(5) 0.0071(5) 0.0036(5) O3 0.0266(7) 0.0325(7) 0.0295(7) 0.0025(5) 0.0113(5) 0.0080(5) O4 0.0216(6) 0.0278(6) 0.0377(7) -0.0042(5) 0.0159(5) -0.0056(5) N1 0.0213(8) 0.0524(10) 0.0304(9) 0.0069(8) 0.0050(6) 0.0005(7) N2 0.0176(7) 0.0395(9) 0.0298(8) 0.0110(7) 0.0095(6) 0.0022(6) C1 0.0155(7) 0.0274(8) 0.0207(8) -0.0023(7) 0.0065(6) -0.0018(6) C2 0.0150(7) 0.0275(8) 0.0215(8) 0.0010(7) 0.0044(6) -0.0013(6) C3 0.0179(8) 0.0270(8) 0.0227(8) 0.0004(7) 0.0052(6) -0.0003(6) C4 0.0158(7) 0.0275(8) 0.0260(9) -0.0030(7) 0.0064(6) -0.0002(6) C5 0.0179(8) 0.0236(8) 0.0251(8) -0.0040(7) 0.0060(6) -0.0009(6) C6 0.0243(9) 0.0312(9) 0.0306(10) 0.0025(8) 0.0038(7) 0.0008(7) C7 0.0227(9) 0.0304(10) 0.0415(11) 0.0011(8) 0.0028(8) 0.0051(7) C8 0.0205(8) 0.0356(10) 0.0449(11) -0.0038(9) 0.0099(8) 0.0043(7) C9 0.0217(9) 0.0309(9) 0.0347(10) -0.0054(8) 0.0125(7) -0.0015(7) C10 0.0199(8) 0.0308(9) 0.0233(8) 0.0012(7) 0.0079(7) -0.0025(7) C11 0.0285(10) 0.0464(12) 0.0400(11) 0.0017(9) 0.0165(8) 0.0121(8) C12 0.0326(11) 0.0333(11) 0.0757(17) -0.0167(11) 0.0151(11) 0.0036(9) C13 0.0458(13) 0.0344(11) 0.0837(19) 0.0188(12) 0.0284(13) 0.0069(10) C14 0.0433(14) 0.085(2) 0.0675(18) 0.0257(16) 0.0096(12) 0.0124(14) C15 0.0250(10) 0.0281(9) 0.0510(13) -0.0007(9) 0.0114(8) -0.0077(7) C16 0.0261(10) 0.0456(12) 0.0526(14) -0.0098(10) 0.0184(9) -0.0134(8) C17 0.0230(10) 0.0502(14) 0.091(2) 0.0010(13) 0.0152(11) -0.0004(9) C18 0.0475(15) 0.106(3) 0.0668(19) 0.0245(18) 0.0172(14) 0.0134(16) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 '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 O3 114.68(7) . . ? O1 P1 O4 115.60(7) . . ? O3 P1 O4 103.60(7) . . ? O1 P1 C1 113.25(8) . . ? O3 P1 C1 106.37(8) . . ? O4 P1 C1 102.00(7) . . ? C3 O2 C4 118.26(14) . . ? C11 O3 P1 122.70(12) . . ? C15 O4 P1 118.02(12) . . ? C3 N2 H2A 117.2(16) . . ? C3 N2 H2B 122.1(16) . . ? H2A N2 H2B 120(2) . . ? C5 C1 C2 109.48(14) . . ? C5 C1 P1 109.79(11) . . ? C2 C1 P1 109.00(12) . . ? C5 C1 H1 109.5 . . ? C2 C1 H1 109.5 . . ? P1 C1 H1 109.5 . . ? C3 C2 C10 118.30(15) . . ? C3 C2 C1 120.90(14) . . ? C10 C2 C1 120.72(15) . . ? N2 C3 O2 110.94(15) . . ? N2 C3 C2 127.44(16) . . ? O2 C3 C2 121.61(15) . . ? C5 C4 C6 122.48(16) . . ? C5 C4 O2 122.12(15) . . ? C6 C4 O2 115.40(16) . . ? C4 C5 C9 117.81(16) . . ? C4 C5 C1 119.58(15) . . ? C9 C5 C1 122.58(16) . . ? C4 C6 C7 118.69(18) . . ? C4 C6 H6 120.7 . . ? C7 C6 H6 120.7 . . ? C6 C7 C8 120.24(18) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C9 C8 C7 120.09(17) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C5 120.70(18) . . ? C8 C9 H9 119.7 . . ? C5 C9 H9 119.7 . . ? N1 C10 C2 179.1(2) . . ? O3 C11 C12 108.31(18) . . ? O3 C11 H11A 110.0 . . ? C12 C11 H11A 110.0 . . ? O3 C11 H11B 110.0 . . ? C12 C11 H11B 110.0 . . ? H11A C11 H11B 108.4 . . ? C13 C12 C11 114.96(19) . . ? C13 C12 H12A 108.5 . . ? C11 C12 H12A 108.5 . . ? C13 C12 H12B 108.5 . . ? C11 C12 H12B 108.5 . . ? H12A C12 H12B 107.5 . . ? C12 C13 C14 113.7(2) . . ? C12 C13 H13A 108.8 . . ? C14 C13 H13A 108.8 . . ? C12 C13 H13B 108.8 . . ? C14 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O4 C15 C16 108.50(16) . . ? O4 C15 H15A 110.0 . . ? C16 C15 H15A 110.0 . . ? O4 C15 H15B 110.0 . . ? C16 C15 H15B 110.0 . . ? H15A C15 H15B 108.4 . . ? C15 C16 C17 114.24(19) . . ? C15 C16 H16A 108.7 . . ? C17 C16 H16A 108.7 . . ? C15 C16 H16B 108.7 . . ? C17 C16 H16B 108.7 . . ? H16A C16 H16B 107.6 . . ? C16 C17 C18 112.3(2) . . ? C16 C17 H17A 109.1 . . ? C18 C17 H17A 109.1 . . ? C16 C17 H17B 109.1 . . ? C18 C17 H17B 109.1 . . ? H17A C17 H17B 107.9 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 1.4661(13) . ? P1 O3 1.5729(13) . ? P1 O4 1.5766(12) . ? P1 C1 1.8145(17) . ? O2 C3 1.358(2) . ? O2 C4 1.394(2) . ? O3 C11 1.463(2) . ? O4 C15 1.463(2) . ? N1 C10 1.149(2) . ? N2 C3 1.329(2) . ? N2 H2A 0.908(16) . ? N2 H2B 0.875(16) . ? C1 C5 1.510(2) . ? C1 C2 1.514(2) . ? C1 H1 1.0000 . ? C2 C3 1.372(2) . ? C2 C10 1.409(2) . ? C4 C5 1.383(3) . ? C4 C6 1.384(3) . ? C5 C9 1.398(2) . ? C6 C7 1.386(3) . ? C6 H6 0.9500 . ? C7 C8 1.387(3) . ? C7 H7 0.9500 . ? C8 C9 1.383(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C11 C12 1.520(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.512(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.519(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.511(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.513(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.540(5) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 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 0.908(16) 1.887(16) 2.793(2) 175(2) 2_655 yes N2 H2B N1 0.875(16) 2.157(17) 3.015(2) 167(2) 3_766 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 O3 C11 16.63(18) . . . . ? O4 P1 O3 C11 143.53(15) . . . . ? C1 P1 O3 C11 -109.37(16) . . . . ? O1 P1 O4 C15 54.90(16) . . . . ? O3 P1 O4 C15 -71.41(15) . . . . ? C1 P1 O4 C15 178.23(14) . . . . ? O1 P1 C1 C5 51.11(14) . . . . ? O3 P1 C1 C5 177.97(11) . . . . ? O4 P1 C1 C5 -73.79(13) . . . . ? O1 P1 C1 C2 -68.81(13) . . . . ? O3 P1 C1 C2 58.05(13) . . . . ? O4 P1 C1 C2 166.29(11) . . . . ? C5 C1 C2 C3 -27.5(2) . . . . ? P1 C1 C2 C3 92.62(18) . . . . ? C5 C1 C2 C10 155.81(16) . . . . ? P1 C1 C2 C10 -84.07(18) . . . . ? C4 O2 C3 N2 -163.56(15) . . . . ? C4 O2 C3 C2 15.7(2) . . . . ? C10 C2 C3 N2 5.1(3) . . . . ? C1 C2 C3 N2 -171.66(17) . . . . ? C10 C2 C3 O2 -173.98(16) . . . . ? C1 C2 C3 O2 9.2(3) . . . . ? C3 O2 C4 C5 -19.8(2) . . . . ? C3 O2 C4 C6 160.96(16) . . . . ? C6 C4 C5 C9 -0.2(3) . . . . ? O2 C4 C5 C9 -179.41(16) . . . . ? C6 C4 C5 C1 177.76(16) . . . . ? O2 C4 C5 C1 -1.5(2) . . . . ? C2 C1 C5 C4 23.3(2) . . . . ? P1 C1 C5 C4 -96.38(16) . . . . ? C2 C1 C5 C9 -158.90(16) . . . . ? P1 C1 C5 C9 81.47(18) . . . . ? C5 C4 C6 C7 -0.4(3) . . . . ? O2 C4 C6 C7 178.84(16) . . . . ? C4 C6 C7 C8 1.0(3) . . . . ? C6 C7 C8 C9 -0.9(3) . . . . ? C7 C8 C9 C5 0.3(3) . . . . ? C4 C5 C9 C8 0.3(3) . . . . ? C1 C5 C9 C8 -177.60(17) . . . . ? P1 O3 C11 C12 -131.82(16) . . . . ? O3 C11 C12 C13 -62.9(2) . . . . ? C11 C12 C13 C14 -63.5(3) . . . . ? P1 O4 C15 C16 -151.38(15) . . . . ? O4 C15 C16 C17 63.4(3) . . . . ? C15 C16 C17 C18 66.2(3) . . . . ?