#------------------------------------------------------------------------------ #$Date: 2020-01-24 06:40:06 +0200 (Fri, 24 Jan 2020) $ #$Revision: 247182 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/71/1557144.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_1557144 loop_ _publ_author_name 'Hirai, Yuichi' 'Wrona-Piotrowicz, Anna' 'Zakrzewski, Janusz' 'Brosseau, Arnaud' 'Guillot, R\'egis' 'M\'etivier, R\'emi' 'Allain, Cl\'emence' _publ_section_title ; Mechanofluorochromism of pyrene-derived amidophosphonates ; _journal_name_full 'Photochemical & Photobiological Sciences' _journal_paper_doi 10.1039/C9PP00457B _journal_year 2020 _chemical_formula_moiety 'C25 H28 N O4 P' _chemical_formula_sum 'C25 H28 N O4 P' _chemical_formula_weight 437.45 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _audit_block_doi 10.5517/ccdc.csd.cc247b7z _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2019-12-20 deposited with the CCDC. 2020-01-23 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 110.5060(10) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 26.8408(13) _cell_length_b 9.9974(5) _cell_length_c 17.4578(8) _cell_measurement_reflns_used 9915 _cell_measurement_temperature 100(1) _cell_measurement_theta_max 66.64 _cell_measurement_theta_min 3.52 _cell_volume 4387.8(4) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX3' _computing_data_reduction 'Bruker SAINT' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 100(1) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker VENTURE PHOTON100 CMOS' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_unetI/netI 0.0155 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 36707 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 66.654 _diffrn_reflns_theta_max 66.654 _diffrn_reflns_theta_min 3.516 _exptl_absorpt_coefficient_mu 1.374 _exptl_absorpt_correction_T_max 0.8528 _exptl_absorpt_correction_T_min 0.7302 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker APEX3' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.324 _exptl_crystal_description block _exptl_crystal_F_000 1856 _exptl_crystal_size_max 0.240 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.140 _refine_diff_density_max 0.339 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.045 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 295 _refine_ls_number_reflns 3865 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.048 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0330 _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^)+(0.0418P)^2^+5.1097P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0852 _refine_ls_wR_factor_ref 0.0856 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3764 _reflns_number_total 3865 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9pp00457b2.cif _cod_data_source_block AP2 _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 1557144 _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 0.748 _shelx_estimated_absorpt_t_max 0.841 _shelx_res_file ; TITL cu_v958_GuillotICMMO.res in C2/c shelx.res created by SHELXL-2018/3 at 13:57:21 on 18-Dec-2019 CELL 1.54178 26.8408 9.9974 17.4578 90.000 110.506 90.000 ZERR 8.00 0.0013 0.0005 0.0008 0.000 0.001 0.000 LATT 7 SYMM - X, Y, 1/2 - Z SFAC C H N O P DISP P 0.29576 0.43416 3772.51 DISP O 0.04946 0.03229 280.59 DISP N 0.03112 0.01806 156.90 DISP C 0.01788 0.00907 78.80 UNIT 200 224 8 32 8 MERG 2 FMAP 2 PLAN 20 SIZE 0.140 0.180 0.240 ACTA 164.00 BOND $H LIST 6 WPDB -2 L.S. 30 TEMP -173.00 WGHT 0.041800 5.109700 FVAR 0.27844 0.65141 C1 1 0.867152 0.263263 0.670322 11.00000 0.01806 0.02402 = 0.02521 0.00645 0.00471 -0.00067 AFIX 43 H1 2 0.900020 0.305007 0.700252 11.00000 -1.20000 AFIX 0 C2 1 0.865993 0.162234 0.615148 11.00000 0.02092 0.02529 = 0.02894 0.00716 0.01154 0.00503 AFIX 43 H2 2 0.898030 0.134600 0.608270 11.00000 -1.20000 AFIX 0 C3 1 0.818315 0.101564 0.570090 11.00000 0.02747 0.01872 = 0.02368 0.00345 0.01260 0.00482 AFIX 43 H3 2 0.817974 0.032915 0.532284 11.00000 -1.20000 AFIX 0 C4 1 0.770759 0.139890 0.579459 11.00000 0.02231 0.01465 = 0.01765 0.00441 0.00712 0.00160 C5 1 0.720456 0.080068 0.533294 11.00000 0.02569 0.01472 = 0.01717 -0.00082 0.00719 0.00008 AFIX 43 H5 2 0.719141 0.013390 0.493861 11.00000 -1.20000 AFIX 0 C6 1 0.674981 0.116292 0.544574 11.00000 0.02007 0.01531 = 0.01624 0.00137 0.00225 -0.00220 AFIX 43 H6 2 0.642557 0.073684 0.513480 11.00000 -1.20000 AFIX 0 C7 1 0.674682 0.218037 0.602697 11.00000 0.01898 0.01293 = 0.01537 0.00432 0.00394 0.00028 C8 1 0.723822 0.281232 0.648529 11.00000 0.01898 0.01209 = 0.01395 0.00414 0.00411 0.00041 C9 1 0.771654 0.241933 0.636655 11.00000 0.01926 0.01449 = 0.01509 0.00502 0.00509 0.00131 C10 1 0.820767 0.304518 0.682531 11.00000 0.01950 0.01769 = 0.01757 0.00595 0.00374 -0.00026 C11 1 0.820745 0.407352 0.740217 11.00000 0.01946 0.01887 = 0.01942 0.00259 0.00104 -0.00427 AFIX 43 H11 2 0.853196 0.450343 0.770784 11.00000 -1.20000 AFIX 0 C12 1 0.775450 0.443776 0.751650 11.00000 0.02557 0.01635 = 0.01683 -0.00077 0.00402 -0.00167 AFIX 43 H12 2 0.776703 0.511921 0.790207 11.00000 -1.20000 AFIX 0 C13 1 0.725355 0.381903 0.706867 11.00000 0.02153 0.01399 = 0.01568 0.00349 0.00502 0.00081 C14 1 0.678356 0.417677 0.719148 11.00000 0.02613 0.01563 = 0.01836 -0.00075 0.00813 0.00125 AFIX 43 H14 2 0.679117 0.483188 0.758961 11.00000 -1.20000 AFIX 0 C15 1 0.630646 0.357699 0.673317 11.00000 0.02003 0.01710 = 0.02314 0.00381 0.00967 0.00294 AFIX 43 H15 2 0.598858 0.384472 0.681311 11.00000 -1.20000 AFIX 0 C16 1 0.628287 0.259165 0.615874 11.00000 0.01839 0.01421 = 0.01903 0.00518 0.00491 0.00020 C17 1 0.576102 0.191606 0.571517 11.00000 0.01797 0.01737 = 0.02317 0.00133 0.00826 -0.00056 C18 1 0.483106 0.223259 0.483925 11.00000 0.01590 0.01487 = 0.02111 -0.00092 0.00722 -0.00256 AFIX 13 H18 2 0.482885 0.127915 0.501123 11.00000 -1.20000 AFIX 0 C19 1 0.421821 0.277790 0.660514 11.00000 0.04154 0.02958 = 0.03005 -0.00007 0.02352 0.00411 AFIX 23 H19A 2 0.394303 0.345925 0.634596 11.00000 -1.20000 H19B 2 0.444728 0.312066 0.714593 11.00000 -1.20000 AFIX 0 PART 1 C20A 1 0.395854 0.150381 0.671141 21.00000 0.07454 0.03064 = 0.06239 -0.00357 0.05238 -0.00962 AFIX 137 H20A 2 0.372746 0.117601 0.617569 21.00000 -1.50000 H20B 2 0.374567 0.166634 0.705773 21.00000 -1.50000 H20C 2 0.423222 0.083357 0.697052 21.00000 -1.50000 AFIX 0 PART 0 C21 1 0.338323 0.320658 0.412378 11.00000 0.02178 0.02338 = 0.02167 0.00045 0.00656 -0.00132 AFIX 23 H21A 2 0.339334 0.297160 0.357853 11.00000 -1.20000 H21B 2 0.344031 0.418255 0.420407 11.00000 -1.20000 AFIX 0 C22 1 0.285414 0.282954 0.417412 11.00000 0.02042 0.02355 = 0.03745 0.00061 0.00835 -0.00082 AFIX 137 H22A 2 0.279446 0.186853 0.407223 11.00000 -1.50000 H22B 2 0.257172 0.333111 0.376275 11.00000 -1.50000 H22C 2 0.285087 0.304287 0.472024 11.00000 -1.50000 AFIX 0 C23 1 0.468183 0.222019 0.390136 11.00000 0.01902 0.02334 = 0.01976 -0.00450 0.00666 -0.00477 AFIX 13 H23 2 0.431445 0.184484 0.365869 11.00000 -1.20000 AFIX 0 C24 1 0.505739 0.128207 0.367920 11.00000 0.02983 0.02878 = 0.02643 -0.00489 0.01596 -0.00340 AFIX 137 H24A 2 0.495377 0.123475 0.308291 11.00000 -1.50000 H24B 2 0.503780 0.038753 0.389646 11.00000 -1.50000 H24C 2 0.542222 0.162036 0.391528 11.00000 -1.50000 AFIX 0 C25 1 0.467854 0.360603 0.353529 11.00000 0.02908 0.02863 = 0.02058 0.00073 0.00638 -0.00208 AFIX 137 H25A 2 0.458599 0.352852 0.294195 11.00000 -1.50000 H25B 2 0.503194 0.401059 0.377517 11.00000 -1.50000 H25C 2 0.441559 0.416985 0.365343 11.00000 -1.50000 AFIX 0 N1 3 0.536625 0.274274 0.527551 11.00000 0.01592 0.01373 = 0.02088 0.00031 0.00551 -0.00230 AFIX 43 H10 2 0.543223 0.360088 0.525137 11.00000 -1.20000 AFIX 0 O1 4 0.570742 0.070530 0.577299 11.00000 0.01978 0.01508 = 0.04504 0.00503 0.00800 -0.00188 O2 4 0.453713 0.254126 0.609602 11.00000 0.02786 0.02941 = 0.02416 0.00215 0.01434 0.00451 O3 4 0.379891 0.248257 0.475921 11.00000 0.01709 0.01800 = 0.03225 0.00128 0.00911 -0.00199 O4 4 0.436483 0.458727 0.513234 11.00000 0.02053 0.01662 = 0.03013 -0.00223 0.00985 -0.00182 P1 5 0.436674 0.311873 0.520051 11.00000 0.01655 0.01487 = 0.02200 -0.00088 0.00883 -0.00135 PART 2 C20B 1 0.420491 0.150381 0.702738 -21.00000 0.11569 0.03402 = 0.08286 0.00158 0.08268 0.00227 AFIX 137 H20D 2 0.404975 0.080310 0.662105 -21.00000 -1.50000 H20E 2 0.398848 0.161425 0.737339 -21.00000 -1.50000 H20F 2 0.456770 0.124949 0.736761 -21.00000 -1.50000 AFIX 0 HKLF 4 REM cu_v958_GuillotICMMO.res in C2/c REM wR2 = 0.0856, GooF = S = 1.048, Restrained GooF = 1.048 for all data REM R1 = 0.0330 for 3764 Fo > 4sig(Fo) and 0.0335 for all 3865 data REM 295 parameters refined using 0 restraints END WGHT 0.0418 5.1098 REM Highest difference peak 0.339, deepest hole -0.382, 1-sigma level 0.045 Q1 1 0.4263 0.3369 0.4653 11.00000 0.05 0.34 Q2 1 0.4609 0.2627 0.4990 11.00000 0.05 0.33 Q3 1 0.4507 0.3621 0.6883 11.00000 0.05 0.28 Q4 1 0.4724 0.2950 0.3757 11.00000 0.05 0.25 Q5 1 0.4294 0.2750 0.3956 11.00000 0.05 0.24 Q6 1 0.5242 0.2757 0.5746 11.00000 0.05 0.24 Q7 1 0.4768 0.2309 0.4391 11.00000 0.05 0.22 Q8 1 0.6992 0.2493 0.6275 11.00000 0.05 0.22 Q9 1 0.7943 0.2809 0.6482 11.00000 0.05 0.20 Q10 1 0.7482 0.2769 0.6333 11.00000 0.05 0.19 Q11 1 0.4716 0.2178 0.5577 11.00000 0.05 0.18 Q12 1 0.5605 0.0792 0.6226 11.00000 0.05 0.18 Q13 1 0.7468 0.1070 0.5648 11.00000 0.05 0.17 Q14 1 0.6500 0.2214 0.6176 11.00000 0.05 0.17 Q15 1 0.8183 0.3571 0.6990 11.00000 0.05 0.17 Q16 1 0.6035 0.2304 0.5888 11.00000 0.05 0.17 Q17 1 0.7697 0.2023 0.5989 11.00000 0.05 0.17 Q18 1 0.4417 0.4793 0.4752 11.00000 0.05 0.16 Q19 1 0.3812 0.2846 0.6211 11.00000 0.05 0.15 Q20 1 0.6782 0.1579 0.5852 11.00000 0.05 0.15 ; _shelx_res_checksum 69752 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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 C1 C 0.86715(6) 0.26326(15) 0.67032(9) 0.0232(3) Uani 1 1 d . . . . . H1 H 0.900020 0.305007 0.700252 0.028 Uiso 1 1 calc R U . . . C2 C 0.86599(6) 0.16223(15) 0.61515(9) 0.0243(3) Uani 1 1 d . . . . . H2 H 0.898030 0.134600 0.608270 0.029 Uiso 1 1 calc R U . . . C3 C 0.81832(6) 0.10156(14) 0.57009(9) 0.0223(3) Uani 1 1 d . . . . . H3 H 0.817974 0.032915 0.532284 0.027 Uiso 1 1 calc R U . . . C4 C 0.77076(5) 0.13989(13) 0.57946(8) 0.0182(3) Uani 1 1 d . . . . . C5 C 0.72046(5) 0.08007(13) 0.53329(8) 0.0193(3) Uani 1 1 d . . . . . H5 H 0.719141 0.013390 0.493861 0.023 Uiso 1 1 calc R U . . . C6 C 0.67498(5) 0.11629(13) 0.54457(8) 0.0183(3) Uani 1 1 d . . . . . H6 H 0.642557 0.073684 0.513480 0.022 Uiso 1 1 calc R U . . . C7 C 0.67468(5) 0.21804(13) 0.60270(8) 0.0163(3) Uani 1 1 d . . . . . C8 C 0.72382(5) 0.28123(13) 0.64853(8) 0.0154(3) Uani 1 1 d . . . . . C9 C 0.77165(5) 0.24193(13) 0.63666(8) 0.0165(3) Uani 1 1 d . . . . . C10 C 0.82077(5) 0.30452(13) 0.68253(8) 0.0190(3) Uani 1 1 d . . . . . C11 C 0.82075(5) 0.40735(14) 0.74022(8) 0.0208(3) Uani 1 1 d . . . . . H11 H 0.853196 0.450343 0.770784 0.025 Uiso 1 1 calc R U . . . C12 C 0.77545(6) 0.44378(14) 0.75165(8) 0.0205(3) Uani 1 1 d . . . . . H12 H 0.776703 0.511921 0.790207 0.025 Uiso 1 1 calc R U . . . C13 C 0.72536(5) 0.38190(13) 0.70687(8) 0.0175(3) Uani 1 1 d . . . . . C14 C 0.67836(6) 0.41768(14) 0.71915(8) 0.0199(3) Uani 1 1 d . . . . . H14 H 0.679117 0.483188 0.758961 0.024 Uiso 1 1 calc R U . . . C15 C 0.63065(5) 0.35770(14) 0.67332(8) 0.0195(3) Uani 1 1 d . . . . . H15 H 0.598858 0.384472 0.681311 0.023 Uiso 1 1 calc R U . . . C16 C 0.62829(5) 0.25917(13) 0.61587(8) 0.0176(3) Uani 1 1 d . . . . . C17 C 0.57610(5) 0.19161(13) 0.57152(8) 0.0192(3) Uani 1 1 d . . . . . C18 C 0.48311(5) 0.22326(13) 0.48393(8) 0.0171(3) Uani 1 1 d . . . . . H18 H 0.482885 0.127915 0.501123 0.021 Uiso 1 1 calc R U . . . C19 C 0.42182(7) 0.27779(16) 0.66051(10) 0.0308(4) Uani 1 1 d . . . . . H19A H 0.394303 0.345925 0.634596 0.037 Uiso 1 1 calc R U . A 1 H19B H 0.444728 0.312066 0.714593 0.037 Uiso 1 1 calc R U . A 1 C20A C 0.3959(5) 0.1504(7) 0.6711(6) 0.0483(16) Uani 0.65(3) 1 d . . P B 1 H20A H 0.372746 0.117601 0.617569 0.072 Uiso 0.65(3) 1 calc R U P B 1 H20B H 0.374567 0.166634 0.705773 0.072 Uiso 0.65(3) 1 calc R U P B 1 H20C H 0.423222 0.083357 0.697052 0.072 Uiso 0.65(3) 1 calc R U P B 1 C21 C 0.33832(5) 0.32066(14) 0.41238(9) 0.0226(3) Uani 1 1 d . . . . . H21A H 0.339334 0.297160 0.357853 0.027 Uiso 1 1 calc R U . . . H21B H 0.344031 0.418255 0.420407 0.027 Uiso 1 1 calc R U . . . C22 C 0.28541(6) 0.28295(15) 0.41741(10) 0.0276(3) Uani 1 1 d . . . . . H22A H 0.279446 0.186853 0.407223 0.041 Uiso 1 1 calc R U . . . H22B H 0.257172 0.333111 0.376275 0.041 Uiso 1 1 calc R U . . . H22C H 0.285087 0.304287 0.472024 0.041 Uiso 1 1 calc R U . . . C23 C 0.46818(5) 0.22202(14) 0.39014(8) 0.0207(3) Uani 1 1 d . . . . . H23 H 0.431445 0.184484 0.365869 0.025 Uiso 1 1 calc R U . . . C24 C 0.50574(6) 0.12821(16) 0.36792(9) 0.0267(3) Uani 1 1 d . . . . . H24A H 0.495377 0.123475 0.308291 0.040 Uiso 1 1 calc R U . . . H24B H 0.503780 0.038753 0.389646 0.040 Uiso 1 1 calc R U . . . H24C H 0.542222 0.162036 0.391528 0.040 Uiso 1 1 calc R U . . . C25 C 0.46785(6) 0.36060(15) 0.35353(9) 0.0267(3) Uani 1 1 d . . . . . H25A H 0.458599 0.352852 0.294195 0.040 Uiso 1 1 calc R U . . . H25B H 0.503194 0.401059 0.377517 0.040 Uiso 1 1 calc R U . . . H25C H 0.441559 0.416985 0.365343 0.040 Uiso 1 1 calc R U . . . N1 N 0.53663(4) 0.27427(11) 0.52755(7) 0.0171(2) Uani 1 1 d . . . . . H10 H 0.543223 0.360088 0.525137 0.021 Uiso 1 1 calc R U . . . O1 O 0.57074(4) 0.07053(10) 0.57730(7) 0.0275(2) Uani 1 1 d . . . . . O2 O 0.45371(4) 0.25413(10) 0.60960(6) 0.0258(2) Uani 1 1 d . . . . . O3 O 0.37989(4) 0.24826(9) 0.47592(6) 0.0223(2) Uani 1 1 d . . . . . O4 O 0.43648(4) 0.45873(10) 0.51323(6) 0.0222(2) Uani 1 1 d . . . . . P1 P 0.43667(2) 0.31187(3) 0.52005(2) 0.01725(11) Uani 1 1 d . . . . . C20B C 0.4205(13) 0.1504(13) 0.7027(17) 0.065(5) Uani 0.35(3) 1 d . . P B 2 H20D H 0.404975 0.080310 0.662105 0.097 Uiso 0.35(3) 1 calc R U P B 2 H20E H 0.398848 0.161425 0.737339 0.097 Uiso 0.35(3) 1 calc R U P B 2 H20F H 0.456770 0.124949 0.736761 0.097 Uiso 0.35(3) 1 calc R U P B 2 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 0.0181(7) 0.0240(7) 0.0252(7) 0.0064(6) 0.0047(6) -0.0007(6) C2 0.0209(7) 0.0253(7) 0.0289(8) 0.0072(6) 0.0115(6) 0.0050(6) C3 0.0275(7) 0.0187(7) 0.0237(7) 0.0035(5) 0.0126(6) 0.0048(6) C4 0.0223(7) 0.0147(6) 0.0176(6) 0.0044(5) 0.0071(5) 0.0016(5) C5 0.0257(7) 0.0147(6) 0.0172(6) -0.0008(5) 0.0072(5) 0.0001(5) C6 0.0201(7) 0.0153(6) 0.0162(6) 0.0014(5) 0.0022(5) -0.0022(5) C7 0.0190(6) 0.0129(6) 0.0154(6) 0.0043(5) 0.0039(5) 0.0003(5) C8 0.0190(6) 0.0121(6) 0.0139(6) 0.0041(5) 0.0041(5) 0.0004(5) C9 0.0193(7) 0.0145(6) 0.0151(6) 0.0050(5) 0.0051(5) 0.0013(5) C10 0.0195(7) 0.0177(7) 0.0176(6) 0.0059(5) 0.0037(5) -0.0003(5) C11 0.0195(7) 0.0189(7) 0.0194(7) 0.0026(5) 0.0010(5) -0.0043(5) C12 0.0256(7) 0.0164(7) 0.0168(6) -0.0008(5) 0.0040(5) -0.0017(5) C13 0.0215(7) 0.0140(6) 0.0157(6) 0.0035(5) 0.0050(5) 0.0008(5) C14 0.0261(7) 0.0156(6) 0.0184(6) -0.0008(5) 0.0081(6) 0.0013(5) C15 0.0200(7) 0.0171(7) 0.0231(7) 0.0038(5) 0.0097(5) 0.0029(5) C16 0.0184(7) 0.0142(6) 0.0190(6) 0.0052(5) 0.0049(5) 0.0002(5) C17 0.0180(7) 0.0174(7) 0.0232(7) 0.0013(5) 0.0083(5) -0.0006(5) C18 0.0159(6) 0.0149(6) 0.0211(7) -0.0009(5) 0.0072(5) -0.0026(5) C19 0.0415(9) 0.0296(8) 0.0301(8) -0.0001(6) 0.0235(7) 0.0041(7) C20A 0.075(4) 0.0306(18) 0.062(4) -0.004(2) 0.052(3) -0.010(3) C21 0.0218(7) 0.0234(7) 0.0217(7) 0.0004(6) 0.0066(6) -0.0013(6) C22 0.0204(7) 0.0236(8) 0.0375(8) 0.0006(6) 0.0084(6) -0.0008(6) C23 0.0190(7) 0.0233(7) 0.0198(7) -0.0045(6) 0.0067(5) -0.0048(6) C24 0.0298(8) 0.0288(8) 0.0264(8) -0.0049(6) 0.0160(6) -0.0034(6) C25 0.0291(8) 0.0286(8) 0.0206(7) 0.0007(6) 0.0064(6) -0.0021(6) N1 0.0159(5) 0.0137(5) 0.0209(6) 0.0003(4) 0.0055(4) -0.0023(4) O1 0.0198(5) 0.0151(5) 0.0450(6) 0.0050(4) 0.0080(5) -0.0019(4) O2 0.0279(5) 0.0294(6) 0.0242(5) 0.0022(4) 0.0143(4) 0.0045(4) O3 0.0171(5) 0.0180(5) 0.0323(5) 0.0013(4) 0.0091(4) -0.0020(4) O4 0.0205(5) 0.0166(5) 0.0301(5) -0.0022(4) 0.0098(4) -0.0018(4) P1 0.01655(18) 0.01487(19) 0.02200(19) -0.00088(12) 0.00883(14) -0.00135(12) C20B 0.116(12) 0.034(4) 0.083(10) 0.002(6) 0.083(10) 0.002(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0179 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 0.0181 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0495 0.0323 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2958 0.4342 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _citation_id _citation_doi _citation_year 1 10.1039/C9PP00457B 2020 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 C1 C10 121.07(13) C2 C1 H1 119.5 C10 C1 H1 119.5 C3 C2 C1 120.28(13) C3 C2 H2 119.9 C1 C2 H2 119.9 C2 C3 C4 120.93(13) C2 C3 H3 119.5 C4 C3 H3 119.5 C3 C4 C9 119.21(13) C3 C4 C5 122.53(13) C9 C4 C5 118.27(12) C6 C5 C4 121.69(12) C6 C5 H5 119.2 C4 C5 H5 119.2 C5 C6 C7 121.36(12) C5 C6 H6 119.3 C7 C6 H6 119.3 C16 C7 C8 118.45(12) C16 C7 C6 123.14(12) C8 C7 C6 118.40(12) C13 C8 C9 119.84(12) C13 C8 C7 120.24(12) C9 C8 C7 119.91(12) C4 C9 C10 119.63(12) C4 C9 C8 120.36(12) C10 C9 C8 120.01(12) C1 C10 C9 118.88(13) C1 C10 C11 122.44(13) C9 C10 C11 118.67(12) C12 C11 C10 121.17(12) C12 C11 H11 119.4 C10 C11 H11 119.4 C11 C12 C13 121.55(13) C11 C12 H12 119.2 C13 C12 H12 119.2 C14 C13 C8 119.31(12) C14 C13 C12 121.94(12) C8 C13 C12 118.75(12) C15 C14 C13 120.10(12) C15 C14 H14 119.9 C13 C14 H14 119.9 C14 C15 C16 121.46(12) C14 C15 H15 119.3 C16 C15 H15 119.3 C15 C16 C7 120.41(12) C15 C16 C17 119.25(12) C7 C16 C17 120.25(12) O1 C17 N1 123.98(12) O1 C17 C16 121.06(12) N1 C17 C16 114.95(11) N1 C18 C23 113.45(10) N1 C18 P1 108.55(9) C23 C18 P1 114.74(9) N1 C18 H18 106.5 C23 C18 H18 106.5 P1 C18 H18 106.5 O2 C19 C20B 106.7(5) O2 C19 C20A 109.7(3) O2 C19 H19A 109.7 C20A C19 H19A 109.7 O2 C19 H19B 109.7 C20A C19 H19B 109.7 H19A C19 H19B 108.2 C19 C20A H20A 109.5 C19 C20A H20B 109.5 H20A C20A H20B 109.5 C19 C20A H20C 109.5 H20A C20A H20C 109.5 H20B C20A H20C 109.5 O3 C21 C22 108.53(11) O3 C21 H21A 110.0 C22 C21 H21A 110.0 O3 C21 H21B 110.0 C22 C21 H21B 110.0 H21A C21 H21B 108.4 C21 C22 H22A 109.5 C21 C22 H22B 109.5 H22A C22 H22B 109.5 C21 C22 H22C 109.5 H22A C22 H22C 109.5 H22B C22 H22C 109.5 C24 C23 C25 111.10(12) C24 C23 C18 109.03(11) C25 C23 C18 113.50(11) C24 C23 H23 107.7 C25 C23 H23 107.7 C18 C23 H23 107.7 C23 C24 H24A 109.5 C23 C24 H24B 109.5 H24A C24 H24B 109.5 C23 C24 H24C 109.5 H24A C24 H24C 109.5 H24B C24 H24C 109.5 C23 C25 H25A 109.5 C23 C25 H25B 109.5 H25A C25 H25B 109.5 C23 C25 H25C 109.5 H25A C25 H25C 109.5 H25B C25 H25C 109.5 C17 N1 C18 120.97(11) C17 N1 H10 119.5 C18 N1 H10 119.5 C19 O2 P1 121.23(10) C21 O3 P1 121.37(8) O4 P1 O2 115.90(6) O4 P1 O3 112.72(5) O2 P1 O3 103.37(6) O4 P1 C18 116.26(6) O2 P1 C18 99.79(6) O3 P1 C18 107.27(6) C19 C20B H20D 109.5 C19 C20B H20E 109.5 H20D C20B H20E 109.5 C19 C20B H20F 109.5 H20D C20B H20F 109.5 H20E C20B H20F 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.388(2) C1 C10 1.397(2) C1 H1 0.9500 C2 C3 1.385(2) C2 H2 0.9500 C3 C4 1.396(2) C3 H3 0.9500 C4 C9 1.4218(19) C4 C5 1.4380(19) C5 C6 1.352(2) C5 H5 0.9500 C6 C7 1.4388(19) C6 H6 0.9500 C7 C16 1.4048(19) C7 C8 1.4281(18) C8 C13 1.4222(19) C8 C9 1.4255(19) C9 C10 1.4251(19) C10 C11 1.439(2) C11 C12 1.349(2) C11 H11 0.9500 C12 C13 1.4371(19) C12 H12 0.9500 C13 C14 1.3981(19) C14 C15 1.386(2) C14 H14 0.9500 C15 C16 1.391(2) C15 H15 0.9500 C16 C17 1.5026(18) C17 O1 1.2273(17) C17 N1 1.3510(18) C18 N1 1.4619(16) C18 C23 1.5434(18) C18 P1 1.8129(13) C18 H18 1.0000 C19 O2 1.4532(17) C19 C20B 1.478(13) C19 C20A 1.494(7) C19 H19A 0.9900 C19 H19B 0.9900 C20A H20A 0.9800 C20A H20B 0.9800 C20A H20C 0.9800 C21 O3 1.4602(17) C21 C22 1.501(2) C21 H21A 0.9900 C21 H21B 0.9900 C22 H22A 0.9800 C22 H22B 0.9800 C22 H22C 0.9800 C23 C24 1.523(2) C23 C25 1.524(2) C23 H23 1.0000 C24 H24A 0.9800 C24 H24B 0.9800 C24 H24C 0.9800 C25 H25A 0.9800 C25 H25B 0.9800 C25 H25C 0.9800 N1 H10 0.8800 O2 P1 1.5766(10) O3 P1 1.5806(10) O4 P1 1.4728(10) C20B H20D 0.9800 C20B H20E 0.9800 C20B H20F 0.9800