#------------------------------------------------------------------------------ #$Date: 2021-11-06 22:43:10 +0200 (Sat, 06 Nov 2021) $ #$Revision: 270511 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158320.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_7158320 loop_ _publ_author_name 'Popovics-T\'oth, N\'ora' 'R\'avai, Bettina' 'Tajti, \'Ad\'am' 'Varga, Bence' 'Bagi, P\'eter' 'Perdih, Franc' 'Szab\'o, P\'al Tam\'as' 'Hackler, Jr, L\'aszl\'o' 'Pusk\'as, L\'aszl\'o G' 'B\'alint, Erika' _publ_section_title ; Three-component synthesis, utilization and biological activity of phosphinoyl-functionalized isoindolinones. ; _journal_issue 40 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 8754 _journal_page_last 8760 _journal_paper_doi 10.1039/d1ob01610e _journal_volume 19 _journal_year 2021 _chemical_formula_moiety 'C24 H24 N O2 P' _chemical_formula_sum 'C24 H24 N O2 P' _chemical_formula_weight 389.41 _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 geom _atom_sites_solution_primary dual _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-07-29 deposited with the CCDC. 2021-09-20 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 115.786(8) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.7785(7) _cell_length_b 17.1967(9) _cell_length_c 11.2241(6) _cell_measurement_reflns_used 3857 _cell_measurement_temperature 150.00(10) _cell_measurement_theta_max 29.5390 _cell_measurement_theta_min 3.0290 _cell_volume 2047.1(2) _computing_cell_refinement 'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)' _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 zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_unetI/netI 0.0438 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 11169 _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 27.485 _diffrn_reflns_theta_min 2.337 _diffrn_source 'micro-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 0.154 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.63658 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.264 _exptl_crystal_description prism _exptl_crystal_F_000 824 _exptl_crystal_size_max 0.600 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.150 _refine_diff_density_max 0.306 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.046 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 254 _refine_ls_number_reflns 4703 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.0597 _refine_ls_R_factor_gt 0.0429 _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^)+(0.0452P)^2^+0.5056P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1008 _refine_ls_wR_factor_ref 0.1157 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3698 _reflns_number_total 4703 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01610e2.cif _cod_data_source_block 7a _cod_depositor_comments 'Adding full bibliography for 7158320--7158321.cif.' _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7158320 _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 0.914 _shelx_estimated_absorpt_t_max 0.977 _shelx_res_file ; TITL moc54.res in P2(1)/c moc54.res created by SHELXL-2018/3 at 15:53:34 on 21-Oct-2020 CELL 0.71073 11.778487 17.19672 11.224141 90 115.7858 90 ZERR 4 0.000735 0.000896 0.000616 0 0.0075 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O P UNIT 96 96 4 8 4 EQIV $1 +X,0.5-Y,-0.5+Z EQIV $2 1-X,-0.5+Y,1.5-Z EQIV $3 2-X,-0.5+Y,1.5-Z L.S. 10 PLAN 20 SIZE 0.6 0.3 0.15 TEMP -123 HTAB C1 O1_$1 HTAB C15 O2_$2 HTAB C22 O2_$3 CONF BOND $H fmap 2 acta SHEL 20.4 0.77 REM REM REM WGHT 0.045200 0.505600 FVAR 0.48966 P1 5 0.663355 0.203471 0.687594 11.00000 0.02863 0.03423 = 0.02033 -0.00035 0.01204 -0.00047 O1 4 0.672780 0.222028 0.820660 11.00000 0.04367 0.04612 = 0.02299 -0.00002 0.01775 0.00099 O2 4 0.770331 0.460879 0.796054 11.00000 0.03430 0.03746 = 0.04365 -0.00806 0.01521 -0.00371 N1 3 0.758840 0.346389 0.685555 11.00000 0.02420 0.03396 = 0.02659 -0.00123 0.01029 -0.00024 C1 1 0.662314 0.293075 0.596484 11.00000 0.02693 0.03469 = 0.02153 -0.00064 0.01112 -0.00195 AFIX 13 H1 2 0.675252 0.281338 0.515991 11.00000 -1.20000 AFIX 0 C2 1 0.543002 0.338615 0.562015 11.00000 0.02796 0.03829 = 0.02360 0.00605 0.01391 0.00173 C3 1 0.419374 0.323477 0.471005 11.00000 0.03053 0.04531 = 0.02828 0.00398 0.00976 -0.00070 AFIX 43 H3 2 0.398541 0.277449 0.419032 11.00000 -1.20000 AFIX 0 C4 1 0.327844 0.377378 0.458489 11.00000 0.02708 0.05516 = 0.03842 0.01081 0.00980 0.00186 AFIX 43 H4 2 0.243001 0.368123 0.396612 11.00000 -1.20000 AFIX 0 C5 1 0.356911 0.444752 0.534195 11.00000 0.03049 0.05195 = 0.04749 0.01040 0.01850 0.01000 AFIX 43 H5 2 0.291961 0.480580 0.524145 11.00000 -1.20000 AFIX 0 C6 1 0.479966 0.460021 0.624221 11.00000 0.03911 0.03893 = 0.04172 0.00417 0.02130 0.00516 AFIX 43 H6 2 0.500801 0.506070 0.676141 11.00000 -1.20000 AFIX 0 C7 1 0.571445 0.406367 0.636293 11.00000 0.02895 0.03529 = 0.02813 0.00626 0.01460 0.00151 C8 1 0.709309 0.410280 0.717252 11.00000 0.03140 0.03359 = 0.02989 0.00409 0.01670 0.00013 C9 1 0.893277 0.327369 0.752914 11.00000 0.02592 0.03719 = 0.02717 0.00087 0.00898 -0.00045 AFIX 23 H9A 2 0.903505 0.276860 0.798787 11.00000 -1.20000 H9B 2 0.936852 0.367438 0.820927 11.00000 -1.20000 AFIX 0 C10 1 0.955663 0.322580 0.660073 11.00000 0.02705 0.03917 = 0.03040 0.00012 0.01156 -0.00137 AFIX 23 H10A 2 0.964847 0.375655 0.631220 11.00000 -1.20000 H10B 2 0.901017 0.292474 0.580484 11.00000 -1.20000 AFIX 0 C11 1 1.084423 0.284286 0.725296 11.00000 0.02615 0.05234 = 0.03932 -0.00324 0.01122 -0.00067 AFIX 23 H11A 2 1.138340 0.313786 0.805957 11.00000 -1.20000 H11B 2 1.074875 0.230871 0.752571 11.00000 -1.20000 AFIX 0 C12 1 1.148633 0.280659 0.634504 11.00000 0.03718 0.11534 = 0.05413 -0.00393 0.02237 0.01327 AFIX 137 H12A 2 1.095934 0.251168 0.554749 11.00000 -1.50000 H12B 2 1.230621 0.254943 0.680255 11.00000 -1.50000 H12C 2 1.160972 0.333513 0.609645 11.00000 -1.50000 AFIX 0 C13 1 0.523442 0.150238 0.586012 11.00000 0.02761 0.03071 = 0.03187 0.00068 0.01366 0.00111 C14 1 0.437671 0.135735 0.636209 11.00000 0.03981 0.04593 = 0.04072 0.01032 0.02068 -0.00242 AFIX 43 H14 2 0.452409 0.155419 0.720784 11.00000 -1.20000 AFIX 0 C15 1 0.329958 0.092602 0.564154 11.00000 0.03770 0.05694 = 0.06584 0.02020 0.02314 -0.00785 AFIX 43 H15 2 0.271810 0.082144 0.599966 11.00000 -1.20000 AFIX 0 C16 1 0.307363 0.065102 0.441565 11.00000 0.03511 0.03582 = 0.07260 -0.00235 0.01067 -0.00671 AFIX 43 H16 2 0.233482 0.035557 0.392307 11.00000 -1.20000 AFIX 0 C17 1 0.390942 0.080033 0.389600 11.00000 0.03626 0.07161 = 0.06118 -0.03098 0.01380 -0.00697 AFIX 43 H17 2 0.374241 0.061354 0.303901 11.00000 -1.20000 AFIX 0 C18 1 0.499345 0.122086 0.461074 11.00000 0.03282 0.07671 = 0.04784 -0.02441 0.01956 -0.01020 AFIX 43 H18 2 0.557471 0.131796 0.424951 11.00000 -1.20000 AFIX 0 C19 1 0.793914 0.145231 0.695672 11.00000 0.02636 0.03200 = 0.02544 -0.00143 0.00888 -0.00228 C20 1 0.865456 0.107632 0.815459 11.00000 0.03883 0.04005 = 0.02821 0.00274 0.01129 0.00024 AFIX 43 H20 2 0.843888 0.113087 0.887336 11.00000 -1.20000 AFIX 0 C21 1 0.967953 0.062341 0.829567 11.00000 0.03594 0.03949 = 0.03811 0.00481 0.00611 0.00438 AFIX 43 H21 2 1.016974 0.037342 0.911538 11.00000 -1.20000 AFIX 0 C22 1 0.999046 0.053398 0.725723 11.00000 0.02764 0.03451 = 0.05062 -0.00438 0.01095 -0.00061 AFIX 43 H22 2 1.069628 0.022516 0.736102 11.00000 -1.20000 AFIX 0 C23 1 0.927499 0.089395 0.606095 11.00000 0.02937 0.04009 = 0.03983 -0.00864 0.01645 -0.00485 AFIX 43 H23 2 0.948359 0.082443 0.533998 11.00000 -1.20000 AFIX 0 C24 1 0.825469 0.135589 0.590650 11.00000 0.02813 0.03644 = 0.02747 -0.00308 0.01073 -0.00384 AFIX 43 H24 2 0.777204 0.160606 0.508494 11.00000 -1.20000 AFIX 0 HKLF 4 REM moc54.res in P2(1)/c REM wR2 = 0.1157, GooF = S = 1.059, Restrained GooF = 1.059 for all data REM R1 = 0.0429 for 3698 Fo > 4sig(Fo) and 0.0597 for all 4703 data REM 254 parameters refined using 0 restraints END WGHT 0.0452 0.5056 REM Highest difference peak 0.306, deepest hole -0.314, 1-sigma level 0.046 Q1 1 0.7399 0.1663 0.6922 11.00000 0.05 0.31 Q2 1 0.5838 0.1778 0.6330 11.00000 0.05 0.30 Q3 1 0.5478 0.3708 0.6042 11.00000 0.05 0.26 Q4 1 0.6651 0.2596 0.6380 11.00000 0.05 0.23 Q5 1 0.6315 0.4179 0.6629 11.00000 0.05 0.22 Q6 1 0.5972 0.3072 0.5759 11.00000 0.05 0.21 Q7 1 0.7137 0.3214 0.6481 11.00000 0.05 0.21 Q8 1 0.5348 0.4367 0.6060 11.00000 0.05 0.21 Q9 1 0.8649 0.0940 0.5967 11.00000 0.05 0.19 Q10 1 0.4878 0.3213 0.5563 11.00000 0.05 0.19 Q11 1 0.8292 0.1341 0.7442 11.00000 0.05 0.18 Q12 1 0.4907 0.3472 0.5056 11.00000 0.05 0.18 Q13 1 0.8613 0.4602 0.8423 11.00000 0.05 0.17 Q14 1 1.0318 0.3150 0.6923 11.00000 0.05 0.17 Q15 1 0.5142 0.1113 0.5233 11.00000 0.05 0.16 Q16 1 0.5644 0.2220 0.7654 11.00000 0.05 0.16 Q17 1 0.3980 0.0957 0.6083 11.00000 0.05 0.15 Q18 1 0.8511 0.1450 0.9230 11.00000 0.05 0.15 Q19 1 0.5321 0.1742 0.3944 11.00000 0.05 0.15 Q20 1 0.9231 0.3208 0.6955 11.00000 0.05 0.15 ; _shelx_res_checksum 4108 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 0.66335(4) 0.20347(3) 0.68759(4) 0.02723(13) Uani 1 1 d . . . . . O1 O 0.67278(11) 0.22203(7) 0.82066(10) 0.0364(3) Uani 1 1 d . . . . . O2 O 0.77033(11) 0.46088(7) 0.79605(12) 0.0391(3) Uani 1 1 d . . . . . N1 N 0.75884(12) 0.34639(8) 0.68555(12) 0.0285(3) Uani 1 1 d . . . . . C1 C 0.66231(14) 0.29307(10) 0.59648(14) 0.0275(3) Uani 1 1 d . . . . . H1 H 0.675252 0.281338 0.515991 0.033 Uiso 1 1 calc R U . . . C2 C 0.54300(15) 0.33862(10) 0.56202(14) 0.0290(4) Uani 1 1 d . . . . . C3 C 0.41937(16) 0.32348(11) 0.47100(16) 0.0358(4) Uani 1 1 d . . . . . H3 H 0.398541 0.277449 0.419032 0.043 Uiso 1 1 calc R U . . . C4 C 0.32784(16) 0.37738(12) 0.45849(18) 0.0418(5) Uani 1 1 d . . . . . H4 H 0.243001 0.368123 0.396612 0.050 Uiso 1 1 calc R U . . . C5 C 0.35691(17) 0.44475(12) 0.53419(18) 0.0428(5) Uani 1 1 d . . . . . H5 H 0.291961 0.480580 0.524145 0.051 Uiso 1 1 calc R U . . . C6 C 0.47997(17) 0.46002(11) 0.62422(18) 0.0386(4) Uani 1 1 d . . . . . H6 H 0.500801 0.506070 0.676141 0.046 Uiso 1 1 calc R U . . . C7 C 0.57145(15) 0.40637(10) 0.63629(15) 0.0300(4) Uani 1 1 d . . . . . C8 C 0.70931(15) 0.41028(10) 0.71725(15) 0.0304(4) Uani 1 1 d . . . . . C9 C 0.89328(14) 0.32737(11) 0.75291(15) 0.0310(4) Uani 1 1 d . . . . . H9A H 0.903505 0.276860 0.798787 0.037 Uiso 1 1 calc R U . . . H9B H 0.936852 0.367438 0.820927 0.037 Uiso 1 1 calc R U . . . C10 C 0.95566(15) 0.32258(11) 0.66007(16) 0.0325(4) Uani 1 1 d . . . . . H10A H 0.964847 0.375655 0.631220 0.039 Uiso 1 1 calc R U . . . H10B H 0.901017 0.292474 0.580484 0.039 Uiso 1 1 calc R U . . . C11 C 1.08442(16) 0.28429(12) 0.72530(18) 0.0404(4) Uani 1 1 d . . . . . H11A H 1.138340 0.313786 0.805957 0.048 Uiso 1 1 calc R U . . . H11B H 1.074875 0.230871 0.752571 0.048 Uiso 1 1 calc R U . . . C12 C 1.1486(2) 0.28066(17) 0.6345(2) 0.0680(7) Uani 1 1 d . . . . . H12A H 1.095934 0.251168 0.554749 0.102 Uiso 1 1 calc R U . . . H12B H 1.230621 0.254943 0.680255 0.102 Uiso 1 1 calc R U . . . H12C H 1.160972 0.333513 0.609645 0.102 Uiso 1 1 calc R U . . . C13 C 0.52344(15) 0.15024(10) 0.58601(15) 0.0298(4) Uani 1 1 d . . . . . C14 C 0.43767(17) 0.13574(12) 0.63621(18) 0.0410(4) Uani 1 1 d . . . . . H14 H 0.452409 0.155419 0.720784 0.049 Uiso 1 1 calc R U . . . C15 C 0.32996(18) 0.09260(13) 0.5642(2) 0.0533(6) Uani 1 1 d . . . . . H15 H 0.271810 0.082144 0.599966 0.064 Uiso 1 1 calc R U . . . C16 C 0.30736(19) 0.06510(12) 0.4416(2) 0.0524(6) Uani 1 1 d . . . . . H16 H 0.233482 0.035557 0.392307 0.063 Uiso 1 1 calc R U . . . C17 C 0.39094(19) 0.08003(14) 0.3896(2) 0.0590(6) Uani 1 1 d . . . . . H17 H 0.374241 0.061354 0.303901 0.071 Uiso 1 1 calc R U . . . C18 C 0.49935(18) 0.12209(14) 0.46107(19) 0.0517(6) Uani 1 1 d . . . . . H18 H 0.557471 0.131796 0.424951 0.062 Uiso 1 1 calc R U . . . C19 C 0.79391(15) 0.14523(10) 0.69567(15) 0.0288(4) Uani 1 1 d . . . . . C20 C 0.86546(17) 0.10763(11) 0.81546(16) 0.0369(4) Uani 1 1 d . . . . . H20 H 0.843888 0.113087 0.887336 0.044 Uiso 1 1 calc R U . . . C21 C 0.96795(17) 0.06234(11) 0.82957(18) 0.0414(4) Uani 1 1 d . . . . . H21 H 1.016974 0.037342 0.911538 0.050 Uiso 1 1 calc R U . . . C22 C 0.99905(16) 0.05340(11) 0.72572(18) 0.0398(4) Uani 1 1 d . . . . . H22 H 1.069628 0.022516 0.736102 0.048 Uiso 1 1 calc R U . . . C23 C 0.92750(16) 0.08939(11) 0.60610(17) 0.0359(4) Uani 1 1 d . . . . . H23 H 0.948359 0.082443 0.533998 0.043 Uiso 1 1 calc R U . . . C24 C 0.82547(15) 0.13559(10) 0.59065(15) 0.0312(4) Uani 1 1 d . . . . . H24 H 0.777204 0.160606 0.508494 0.037 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 0.0286(2) 0.0342(3) 0.02033(19) -0.00035(16) 0.01204(17) -0.00047(17) O1 0.0437(7) 0.0461(7) 0.0230(5) 0.0000(5) 0.0178(5) 0.0010(6) O2 0.0343(7) 0.0375(7) 0.0436(7) -0.0081(6) 0.0152(6) -0.0037(6) N1 0.0242(7) 0.0340(8) 0.0266(6) -0.0012(6) 0.0103(6) -0.0002(6) C1 0.0269(8) 0.0347(9) 0.0215(7) -0.0006(6) 0.0111(6) -0.0020(7) C2 0.0280(8) 0.0383(9) 0.0236(7) 0.0061(7) 0.0139(7) 0.0017(7) C3 0.0305(9) 0.0453(11) 0.0283(8) 0.0040(7) 0.0098(7) -0.0007(8) C4 0.0271(9) 0.0552(13) 0.0384(9) 0.0108(9) 0.0098(8) 0.0019(8) C5 0.0305(9) 0.0519(12) 0.0475(10) 0.0104(9) 0.0185(8) 0.0100(8) C6 0.0391(10) 0.0389(10) 0.0417(9) 0.0042(8) 0.0213(8) 0.0052(8) C7 0.0290(8) 0.0353(9) 0.0281(7) 0.0063(7) 0.0146(7) 0.0015(7) C8 0.0314(8) 0.0336(9) 0.0299(8) 0.0041(7) 0.0167(7) 0.0001(7) C9 0.0259(8) 0.0372(10) 0.0272(7) 0.0009(7) 0.0090(7) -0.0005(7) C10 0.0270(8) 0.0392(10) 0.0304(8) 0.0001(7) 0.0116(7) -0.0014(7) C11 0.0261(9) 0.0523(12) 0.0393(9) -0.0032(8) 0.0112(8) -0.0007(8) C12 0.0372(11) 0.115(2) 0.0541(13) -0.0039(13) 0.0224(10) 0.0133(13) C13 0.0276(8) 0.0307(9) 0.0319(8) 0.0007(7) 0.0137(7) 0.0011(7) C14 0.0398(10) 0.0459(11) 0.0407(9) 0.0103(8) 0.0207(8) -0.0024(8) C15 0.0377(11) 0.0569(14) 0.0658(13) 0.0202(11) 0.0231(10) -0.0079(10) C16 0.0351(10) 0.0358(11) 0.0726(14) -0.0023(10) 0.0107(10) -0.0067(8) C17 0.0363(11) 0.0716(16) 0.0612(13) -0.0310(12) 0.0138(10) -0.0070(11) C18 0.0328(10) 0.0767(16) 0.0478(11) -0.0244(11) 0.0196(9) -0.0102(10) C19 0.0264(8) 0.0320(9) 0.0254(7) -0.0014(6) 0.0089(7) -0.0023(7) C20 0.0388(10) 0.0400(11) 0.0282(8) 0.0027(7) 0.0113(8) 0.0002(8) C21 0.0359(10) 0.0395(11) 0.0381(9) 0.0048(8) 0.0061(8) 0.0044(8) C22 0.0276(9) 0.0345(10) 0.0506(10) -0.0044(8) 0.0110(8) -0.0006(7) C23 0.0294(9) 0.0401(10) 0.0398(9) -0.0086(8) 0.0164(8) -0.0049(7) C24 0.0281(8) 0.0364(9) 0.0275(7) -0.0031(7) 0.0107(7) -0.0038(7) 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 C13 113.29(8) . . ? O1 P1 C19 112.33(7) . . ? C13 P1 C19 106.02(8) . . ? O1 P1 C1 110.96(7) . . ? C13 P1 C1 106.91(7) . . ? C19 P1 C1 106.93(8) . . ? C8 N1 C1 112.95(13) . . ? C8 N1 C9 122.36(13) . . ? C1 N1 C9 123.83(14) . . ? N1 C1 C2 102.16(13) . . ? N1 C1 P1 109.17(10) . . ? C2 C1 P1 110.92(11) . . ? N1 C1 H1 111.4 . . ? C2 C1 H1 111.4 . . ? P1 C1 H1 111.4 . . ? C7 C2 C3 120.03(16) . . ? C7 C2 C1 109.17(14) . . ? C3 C2 C1 130.78(16) . . ? C4 C3 C2 118.03(18) . . ? C4 C3 H3 121.0 . . ? C2 C3 H3 121.0 . . ? C3 C4 C5 121.58(17) . . ? C3 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? C6 C5 C4 120.40(18) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C7 C6 C5 118.02(18) . . ? C7 C6 H6 121.0 . . ? C5 C6 H6 121.0 . . ? C6 C7 C2 121.93(16) . . ? C6 C7 C8 129.22(16) . . ? C2 C7 C8 108.76(15) . . ? O2 C8 N1 125.29(15) . . ? O2 C8 C7 128.21(16) . . ? N1 C8 C7 106.48(14) . . ? N1 C9 C10 113.32(13) . . ? N1 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? N1 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C9 C10 C11 111.92(14) . . ? C9 C10 H10A 109.2 . . ? C11 C10 H10A 109.2 . . ? C9 C10 H10B 109.2 . . ? C11 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? C12 C11 C10 112.38(16) . . ? C12 C11 H11A 109.1 . . ? C10 C11 H11A 109.1 . . ? C12 C11 H11B 109.1 . . ? C10 C11 H11B 109.1 . . ? H11A C11 H11B 107.9 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 119.03(16) . . ? C14 C13 P1 117.84(13) . . ? C18 C13 P1 123.12(13) . . ? C13 C14 C15 120.43(19) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C16 C15 C14 120.02(19) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C17 120.17(19) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C18 120.4(2) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C17 C18 C13 119.98(19) . . ? C17 C18 H18 120.0 . . ? C13 C18 H18 120.0 . . ? C24 C19 C20 119.26(16) . . ? C24 C19 P1 124.02(12) . . ? C20 C19 P1 116.72(13) . . ? C21 C20 C19 120.05(17) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C22 C21 C20 120.40(17) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 C23 119.93(17) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C22 C23 C24 120.44(17) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C23 C24 C19 119.90(16) . . ? C23 C24 H24 120.0 . . ? C19 C24 H24 120.0 . . ? 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 1.4834(11) . ? P1 C13 1.7942(16) . ? P1 C19 1.8041(17) . ? P1 C1 1.8464(17) . ? O2 C8 1.226(2) . ? N1 C8 1.362(2) . ? N1 C1 1.464(2) . ? N1 C9 1.464(2) . ? C1 C2 1.505(2) . ? C1 H1 1.0000 . ? C2 C7 1.386(2) . ? C2 C3 1.392(2) . ? C3 C4 1.382(3) . ? C3 H3 0.9500 . ? C4 C5 1.389(3) . ? C4 H4 0.9500 . ? C5 C6 1.384(3) . ? C5 H5 0.9500 . ? C6 C7 1.380(2) . ? C6 H6 0.9500 . ? C7 C8 1.478(2) . ? C9 C10 1.516(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.518(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.512(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.377(2) . ? C13 C18 1.391(2) . ? C14 C15 1.386(3) . ? C14 H14 0.9500 . ? C15 C16 1.367(3) . ? C15 H15 0.9500 . ? C16 C17 1.369(3) . ? C16 H16 0.9500 . ? C17 C18 1.380(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C24 1.392(2) . ? C19 C20 1.396(2) . ? C20 C21 1.387(3) . ? C20 H20 0.9500 . ? C21 C22 1.374(3) . ? C21 H21 0.9500 . ? C22 C23 1.383(3) . ? C22 H22 0.9500 . ? C23 C24 1.387(2) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? 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 C1 H1 O1 1.00 2.18 3.1622(18) 166.7 4_565 yes C15 H15 O2 0.95 2.54 3.256(2) 132.1 2_646 yes C22 H22 O2 0.95 2.32 3.248(2) 164.1 2_746 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 C8 N1 C1 C2 7.25(16) . . . . ? C9 N1 C1 C2 176.82(13) . . . . ? C8 N1 C1 P1 -110.24(13) . . . . ? C9 N1 C1 P1 59.33(16) . . . . ? O1 P1 C1 N1 43.92(13) . . . . ? C13 P1 C1 N1 167.90(11) . . . . ? C19 P1 C1 N1 -78.90(12) . . . . ? O1 P1 C1 C2 -67.89(12) . . . . ? C13 P1 C1 C2 56.09(12) . . . . ? C19 P1 C1 C2 169.29(11) . . . . ? N1 C1 C2 C7 -5.70(16) . . . . ? P1 C1 C2 C7 110.53(13) . . . . ? N1 C1 C2 C3 172.76(16) . . . . ? P1 C1 C2 C3 -71.02(19) . . . . ? C7 C2 C3 C4 -0.4(2) . . . . ? C1 C2 C3 C4 -178.69(16) . . . . ? C2 C3 C4 C5 -0.3(3) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? C4 C5 C6 C7 -0.3(3) . . . . ? C5 C6 C7 C2 -0.3(3) . . . . ? C5 C6 C7 C8 175.73(16) . . . . ? C3 C2 C7 C6 0.7(2) . . . . ? C1 C2 C7 C6 179.34(15) . . . . ? C3 C2 C7 C8 -176.10(14) . . . . ? C1 C2 C7 C8 2.55(17) . . . . ? C1 N1 C8 O2 175.41(15) . . . . ? C9 N1 C8 O2 5.7(2) . . . . ? C1 N1 C8 C7 -5.97(17) . . . . ? C9 N1 C8 C7 -175.72(13) . . . . ? C6 C7 C8 O2 4.1(3) . . . . ? C2 C7 C8 O2 -179.45(16) . . . . ? C6 C7 C8 N1 -174.51(17) . . . . ? C2 C7 C8 N1 1.98(17) . . . . ? C8 N1 C9 C10 -121.24(17) . . . . ? C1 N1 C9 C10 70.1(2) . . . . ? N1 C9 C10 C11 -166.20(15) . . . . ? C9 C10 C11 C12 -178.85(18) . . . . ? O1 P1 C13 C14 3.34(17) . . . . ? C19 P1 C13 C14 126.97(14) . . . . ? C1 P1 C13 C14 -119.20(14) . . . . ? O1 P1 C13 C18 -175.46(16) . . . . ? C19 P1 C13 C18 -51.82(18) . . . . ? C1 P1 C13 C18 62.01(18) . . . . ? C18 C13 C14 C15 1.1(3) . . . . ? P1 C13 C14 C15 -177.78(15) . . . . ? C13 C14 C15 C16 -1.0(3) . . . . ? C14 C15 C16 C17 0.0(3) . . . . ? C15 C16 C17 C18 0.8(4) . . . . ? C16 C17 C18 C13 -0.7(4) . . . . ? C14 C13 C18 C17 -0.3(3) . . . . ? P1 C13 C18 C17 178.53(17) . . . . ? O1 P1 C19 C24 -163.57(14) . . . . ? C13 P1 C19 C24 72.20(16) . . . . ? C1 P1 C19 C24 -41.61(16) . . . . ? O1 P1 C19 C20 17.01(16) . . . . ? C13 P1 C19 C20 -107.23(14) . . . . ? C1 P1 C19 C20 138.96(13) . . . . ? C24 C19 C20 C21 1.1(3) . . . . ? P1 C19 C20 C21 -179.47(14) . . . . ? C19 C20 C21 C22 -0.7(3) . . . . ? C20 C21 C22 C23 -0.3(3) . . . . ? C21 C22 C23 C24 1.0(3) . . . . ? C22 C23 C24 C19 -0.7(3) . . . . ? C20 C19 C24 C23 -0.4(2) . . . . ? P1 C19 C24 C23 -179.80(13) . . . . ?