#------------------------------------------------------------------------------ #$Date: 2024-07-09 01:22:16 +0300 (Tue, 09 Jul 2024) $ #$Revision: 293309 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/21/1572109.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_1572109 loop_ _publ_author_name 'Minko, Yury' 'Fetrow, Taylor V.' 'Sharma, Shikha' 'Cashman, Brenna K.' 'Tondreau, Aaron M.' _publ_section_title ; Flexible interactions of the rare-earth elements Y, La, and Lu with phosphorus in metallacyclohexane rings ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC02077D _journal_year 2024 _chemical_formula_moiety 'C22 H33 N2 P' _chemical_formula_sum 'C22 H33 N2 P' _chemical_formula_weight 356.47 _chemical_properties_physical Air-sensitive _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _audit_creation_date 2021-04-30 _audit_creation_method ; Olex2 1.2 (compiled Apr 3 2018 11:26:26 for OlexSys, GUI svn.r5486) ; _audit_update_record ; 2024-01-24 deposited with the CCDC. 2024-06-20 downloaded from the CCDC. ; _cell_angle_alpha 97.9300(10) _cell_angle_beta 103.0220(10) _cell_angle_gamma 108.0500(10) _cell_formula_units_Z 2 _cell_length_a 8.9968(3) _cell_length_b 11.2118(4) _cell_length_c 11.8000(5) _cell_measurement_reflns_used 9833 _cell_measurement_temperature 109.0 _cell_measurement_theta_max 31.37 _cell_measurement_theta_min 2.56 _cell_volume 1074.49(7) _computing_cell_refinement 'SAINT V8.38A (?, 2016)' _computing_data_reduction 'SAINT V8.38A (?, 2016)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 109.0 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0183 _diffrn_reflns_av_unetI/netI 0.0175 _diffrn_reflns_Laue_measured_fraction_full 0.991 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 23544 _diffrn_reflns_point_group_measured_fraction_full 0.991 _diffrn_reflns_point_group_measured_fraction_max 0.989 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 31.370 _diffrn_reflns_theta_min 2.564 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.135 _exptl_absorpt_correction_T_max 0.7462 _exptl_absorpt_correction_T_min 0.7216 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016) was used for absorption correction. wR2(int) was 0.0560 before and 0.0335 after correction. The Ratio of minimum to maximum transmission is 0.9670. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.102 _exptl_crystal_description block _exptl_crystal_F_000 388 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.3 _refine_diff_density_max 0.486 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.047 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 241 _refine_ls_number_reflns 6992 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.061 _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_gt 0.0374 _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^)+(0.0519P)^2^+0.3658P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1031 _refine_ls_wR_factor_ref 0.1052 _reflns_Friedel_coverage 0.000 _reflns_number_gt 6514 _reflns_number_total 6992 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc02077d2.cif _cod_data_source_block BiAMP _cod_database_code 1572109 _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_max 0.961 _shelx_estimated_absorpt_t_min 0.954 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C5(H5A,H5B), C6(H6A,H6B) 2.b Aromatic/amide H refined with riding coordinates: C3(H3), C8(H8), C13(H13), C14(H14), C17(H17), C22(H22) 2.c Idealised Me refined as rotating group: C1(H1A,H1B,H1C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C16(H16A,H16B, H16C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C) ; _shelx_res_file ; TITL DAMP_a.res in P-1 damp.res created by SHELXL-2018/3 at 12:55:15 on 30-Apr-2021 CELL 0.71073 8.9968 11.2118 11.8 97.93 103.022 108.05 ZERR 2 0.0003 0.0004 0.0005 0.001 0.001 0.001 LATT 1 SFAC C H N P UNIT 44 66 4 2 L.S. 12 PLAN -12 0 0 SIZE 0.35 0.35 0.3 TEMP -164.15 HTAB BOND $H CONF fmap 2 acta REM REM REM WGHT 0.051900 0.365800 FVAR 1.61196 P1 4 0.724657 0.402203 0.350304 11.00000 0.01389 0.01716 = 0.01328 0.00305 0.00308 0.00650 N1 3 0.880965 0.635258 0.503944 11.00000 0.01706 0.01627 = 0.01744 0.00236 0.00226 0.00793 N2 3 0.809418 0.376989 0.578298 11.00000 0.01451 0.02114 = 0.01408 0.00558 0.00291 0.00761 C1 1 1.111609 0.966583 0.879422 11.00000 0.03399 0.02629 = 0.02185 -0.00143 0.00851 0.00550 AFIX 137 H1A 2 1.046718 0.923898 0.928470 11.00000 -1.50000 H1B 2 1.141833 1.060014 0.904445 11.00000 -1.50000 H1C 2 1.210546 0.944868 0.889431 11.00000 -1.50000 AFIX 0 C2 1 1.012648 0.921885 0.749958 11.00000 0.02190 0.01928 = 0.02226 0.00170 0.00967 0.00385 C3 1 0.994466 0.802314 0.685237 11.00000 0.01775 0.01865 = 0.01985 0.00369 0.00697 0.00638 AFIX 43 H3 2 1.047837 0.750619 0.721985 11.00000 -1.20000 AFIX 0 C4 1 0.898082 0.757459 0.566281 11.00000 0.01526 0.01556 = 0.02048 0.00365 0.00755 0.00613 C5 1 0.737061 0.569769 0.401319 11.00000 0.01636 0.01870 = 0.01979 0.00338 0.00173 0.00815 AFIX 23 H5A 2 0.744715 0.615824 0.335854 11.00000 -1.20000 H5B 2 0.637590 0.569483 0.424108 11.00000 -1.20000 AFIX 0 C6 1 0.665113 0.337221 0.476274 11.00000 0.01547 0.02159 = 0.01455 0.00532 0.00200 0.00609 AFIX 23 H6A 2 0.582595 0.370199 0.497633 11.00000 -1.20000 H6B 2 0.616843 0.242094 0.452778 11.00000 -1.20000 AFIX 0 C7 1 0.793424 0.341108 0.685199 11.00000 0.01760 0.01628 = 0.01432 0.00378 0.00325 0.00724 C8 1 0.642030 0.283886 0.703852 11.00000 0.01754 0.02390 = 0.01567 0.00525 0.00365 0.00711 AFIX 43 H8 2 0.545012 0.269106 0.642788 11.00000 -1.20000 AFIX 0 C9 1 0.631781 0.248129 0.811471 11.00000 0.02303 0.02742 = 0.01739 0.00674 0.00656 0.00681 C10 1 0.467252 0.182782 0.828186 11.00000 0.02701 0.05094 = 0.02357 0.01288 0.01044 0.00458 AFIX 137 H10A 2 0.481531 0.159076 0.905763 11.00000 -1.50000 H10B 2 0.406925 0.105113 0.764498 11.00000 -1.50000 H10C 2 0.406191 0.241616 0.825181 11.00000 -1.50000 AFIX 0 C11 1 0.755336 1.036166 0.516263 11.00000 0.03596 0.02116 = 0.04443 0.01045 0.01138 0.01636 AFIX 137 H11A 2 0.757085 1.106472 0.576563 11.00000 -1.50000 H11B 2 0.642093 0.982722 0.473031 11.00000 -1.50000 H11C 2 0.811939 1.072031 0.460026 11.00000 -1.50000 AFIX 0 C12 1 0.839766 0.955062 0.576510 11.00000 0.02476 0.01697 = 0.03195 0.00723 0.01183 0.00953 C13 1 0.822616 0.835065 0.512322 11.00000 0.01854 0.01734 = 0.02388 0.00552 0.00716 0.00753 AFIX 43 H13 2 0.759000 0.805896 0.431150 11.00000 -1.20000 AFIX 0 C14 1 0.935371 0.364228 0.777079 11.00000 0.01756 0.02072 = 0.01734 0.00567 0.00174 0.00654 AFIX 43 H14 2 1.038944 0.404453 0.765689 11.00000 -1.20000 AFIX 0 C15 1 0.926785 0.329252 0.884285 11.00000 0.02336 0.02354 = 0.01700 0.00615 0.00067 0.00893 C16 1 1.080430 0.353142 0.981783 11.00000 0.02823 0.03837 = 0.02260 0.01189 -0.00295 0.01038 AFIX 137 H16A 2 1.124123 0.284856 0.964822 11.00000 -1.50000 H16B 2 1.055616 0.353512 1.058519 11.00000 -1.50000 H16C 2 1.161381 0.436579 0.985355 11.00000 -1.50000 AFIX 0 C17 1 0.774160 0.270823 0.900710 11.00000 0.02845 0.02859 = 0.01601 0.00875 0.00488 0.00888 AFIX 43 H17 2 0.767581 0.246270 0.973844 11.00000 -1.20000 AFIX 0 C18 1 0.526689 0.333664 0.229518 11.00000 0.01693 0.02715 = 0.01420 0.00484 0.00164 0.00401 C19 1 0.378432 0.341073 0.268076 11.00000 0.01490 0.06056 = 0.02267 0.00909 0.00236 0.00924 AFIX 137 H19A 2 0.280570 0.302095 0.199769 11.00000 -1.50000 H19B 2 0.393556 0.431379 0.297463 11.00000 -1.50000 H19C 2 0.365879 0.294506 0.331779 11.00000 -1.50000 AFIX 0 C20 1 0.546529 0.405176 0.128877 11.00000 0.02624 0.03979 = 0.01645 0.01064 0.00128 0.00644 AFIX 137 H20A 2 0.452152 0.361969 0.058590 11.00000 -1.50000 H20B 2 0.646131 0.405100 0.108304 11.00000 -1.50000 H20C 2 0.553973 0.494131 0.155463 11.00000 -1.50000 AFIX 0 C21 1 0.501969 0.191598 0.183117 11.00000 0.03987 0.02681 = 0.02419 -0.00122 -0.00327 0.00178 AFIX 137 H21A 2 0.486418 0.144510 0.246120 11.00000 -1.50000 H21B 2 0.598196 0.186301 0.160079 11.00000 -1.50000 H21C 2 0.405560 0.153571 0.113622 11.00000 -1.50000 AFIX 0 C22 1 0.934012 0.997380 0.695049 11.00000 0.02952 0.01673 = 0.03043 0.00195 0.01276 0.00763 AFIX 43 H22 2 0.945084 1.078691 0.739287 11.00000 -1.20000 AFIX 0 H1 2 0.891394 0.586095 0.550990 11.00000 0.02489 H2 2 0.892237 0.368054 0.561615 11.00000 0.02644 HKLF 4 REM DAMP_a.res in P-1 REM wR2 = 0.1052, GooF = S = 1.061, Restrained GooF = 1.061 for all data REM R1 = 0.0374 for 6514 Fo > 4sig(Fo) and 0.0402 for all 6992 data REM 241 parameters refined using 0 restraints END WGHT 0.0519 0.3659 REM Instructions for potential hydrogen bonds HTAB N1 N2 EQIV $1 -x+2, -y+1, -z+1 HTAB N2 N1_$1 REM Highest difference peak 0.486, deepest hole -0.324, 1-sigma level 0.047 Q1 1 0.5842 0.4575 0.3879 11.00000 0.05 0.49 Q2 1 0.8401 0.8954 0.5485 11.00000 0.05 0.45 Q3 1 0.7168 0.3133 0.6961 11.00000 0.05 0.42 Q4 1 0.8650 0.7952 0.5383 11.00000 0.05 0.40 Q5 1 0.7000 0.2577 0.8559 11.00000 0.05 0.40 Q6 1 0.9985 0.8614 0.7151 11.00000 0.05 0.40 Q7 1 0.9449 0.7769 0.6299 11.00000 0.05 0.39 Q8 1 0.8619 0.3456 0.7304 11.00000 0.05 0.39 Q9 1 0.9266 0.3369 0.8263 11.00000 0.05 0.37 Q10 1 0.6348 0.2635 0.7585 11.00000 0.05 0.37 Q11 1 0.9741 0.9591 0.7206 11.00000 0.05 0.35 Q12 1 1.0762 0.2792 1.0154 11.00000 0.05 0.34 ; _shelx_res_checksum 55284 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.72466(3) 0.40220(2) 0.35030(2) 0.01470(6) Uani 1 1 d . . . . . N1 N 0.88096(9) 0.63526(7) 0.50394(7) 0.01703(14) Uani 1 1 d . . . . . N2 N 0.80942(9) 0.37699(7) 0.57830(7) 0.01628(14) Uani 1 1 d . . . . . C1 C 1.11161(14) 0.96658(11) 0.87942(9) 0.0293(2) Uani 1 1 d . . . . . H1A H 1.046718 0.923898 0.928470 0.044 Uiso 1 1 calc GR . . . . H1B H 1.141833 1.060014 0.904445 0.044 Uiso 1 1 calc GR . . . . H1C H 1.210546 0.944868 0.889431 0.044 Uiso 1 1 calc GR . . . . C2 C 1.01265(12) 0.92189(9) 0.74996(9) 0.02170(18) Uani 1 1 d . . . . . C3 C 0.99447(11) 0.80231(9) 0.68524(8) 0.01855(16) Uani 1 1 d . . . . . H3 H 1.047837 0.750619 0.721985 0.022 Uiso 1 1 calc R . . . . C4 C 0.89808(10) 0.75746(8) 0.56628(8) 0.01655(15) Uani 1 1 d . . . . . C5 C 0.73706(11) 0.56977(9) 0.40132(8) 0.01850(16) Uani 1 1 d . . . . . H5A H 0.744715 0.615824 0.335854 0.022 Uiso 1 1 calc R . . . . H5B H 0.637590 0.569483 0.424108 0.022 Uiso 1 1 calc R . . . . C6 C 0.66511(10) 0.33722(9) 0.47627(8) 0.01758(16) Uani 1 1 d . . . . . H6A H 0.582595 0.370199 0.497633 0.021 Uiso 1 1 calc R . . . . H6B H 0.616843 0.242094 0.452778 0.021 Uiso 1 1 calc R . . . . C7 C 0.79342(11) 0.34111(8) 0.68520(7) 0.01595(15) Uani 1 1 d . . . . . C8 C 0.64203(11) 0.28389(9) 0.70385(8) 0.01919(16) Uani 1 1 d . . . . . H8 H 0.545012 0.269106 0.642788 0.023 Uiso 1 1 calc R . . . . C9 C 0.63178(12) 0.24813(10) 0.81147(8) 0.02281(18) Uani 1 1 d . . . . . C10 C 0.46725(14) 0.18278(14) 0.82819(10) 0.0351(3) Uani 1 1 d . . . . . H10A H 0.481531 0.159076 0.905763 0.053 Uiso 1 1 calc GR . . . . H10B H 0.406925 0.105113 0.764498 0.053 Uiso 1 1 calc GR . . . . H10C H 0.406191 0.241616 0.825181 0.053 Uiso 1 1 calc GR . . . . C11 C 0.75534(15) 1.03617(11) 0.51626(12) 0.0320(2) Uani 1 1 d . . . . . H11A H 0.757085 1.106472 0.576563 0.048 Uiso 1 1 calc GR . . . . H11B H 0.642093 0.982722 0.473031 0.048 Uiso 1 1 calc GR . . . . H11C H 0.811939 1.072031 0.460026 0.048 Uiso 1 1 calc GR . . . . C12 C 0.83977(12) 0.95506(9) 0.57651(10) 0.02320(18) Uani 1 1 d . . . . . C13 C 0.82262(11) 0.83506(9) 0.51232(9) 0.01933(16) Uani 1 1 d . . . . . H13 H 0.759000 0.805896 0.431150 0.023 Uiso 1 1 calc R . . . . C14 C 0.93537(11) 0.36423(9) 0.77708(8) 0.01901(16) Uani 1 1 d . . . . . H14 H 1.038944 0.404453 0.765689 0.023 Uiso 1 1 calc R . . . . C15 C 0.92679(12) 0.32925(9) 0.88429(8) 0.02185(18) Uani 1 1 d . . . . . C16 C 1.08043(14) 0.35314(12) 0.98178(10) 0.0313(2) Uani 1 1 d . . . . . H16A H 1.124123 0.284856 0.964822 0.047 Uiso 1 1 calc GR . . . . H16B H 1.055616 0.353512 1.058519 0.047 Uiso 1 1 calc GR . . . . H16C H 1.161381 0.436579 0.985355 0.047 Uiso 1 1 calc GR . . . . C17 C 0.77416(13) 0.27082(10) 0.90071(8) 0.02450(19) Uani 1 1 d . . . . . H17 H 0.767581 0.246270 0.973844 0.029 Uiso 1 1 calc R . . . . C18 C 0.52669(11) 0.33366(10) 0.22952(8) 0.02082(17) Uani 1 1 d . . . . . C19 C 0.37843(12) 0.34107(14) 0.26808(10) 0.0343(3) Uani 1 1 d . . . . . H19A H 0.280570 0.302095 0.199769 0.051 Uiso 1 1 calc GR . . . . H19B H 0.393556 0.431379 0.297463 0.051 Uiso 1 1 calc GR . . . . H19C H 0.365879 0.294506 0.331779 0.051 Uiso 1 1 calc GR . . . . C20 C 0.54653(14) 0.40518(12) 0.12888(9) 0.0291(2) Uani 1 1 d . . . . . H20A H 0.452152 0.361969 0.058590 0.044 Uiso 1 1 calc GR . . . . H20B H 0.646131 0.405100 0.108304 0.044 Uiso 1 1 calc GR . . . . H20C H 0.553973 0.494131 0.155463 0.044 Uiso 1 1 calc GR . . . . C21 C 0.50197(16) 0.19160(11) 0.18312(10) 0.0356(3) Uani 1 1 d . . . . . H21A H 0.486418 0.144510 0.246120 0.053 Uiso 1 1 calc GR . . . . H21B H 0.598196 0.186301 0.160079 0.053 Uiso 1 1 calc GR . . . . H21C H 0.405560 0.153571 0.113622 0.053 Uiso 1 1 calc GR . . . . C22 C 0.93401(13) 0.99738(9) 0.69505(10) 0.02531(19) Uani 1 1 d . . . . . H22 H 0.945084 1.078691 0.739287 0.030 Uiso 1 1 calc R . . . . H1 H 0.8914(17) 0.5861(14) 0.5510(13) 0.025(3) Uiso 1 1 d . . . . . H2 H 0.8922(18) 0.3681(14) 0.5616(13) 0.026(3) Uiso 1 1 d . . . . . 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 0.01389(10) 0.01716(11) 0.01328(10) 0.00305(7) 0.00308(7) 0.00650(8) N1 0.0171(3) 0.0163(3) 0.0174(3) 0.0024(3) 0.0023(3) 0.0079(3) N2 0.0145(3) 0.0211(3) 0.0141(3) 0.0056(3) 0.0029(2) 0.0076(3) C1 0.0340(5) 0.0263(5) 0.0219(4) -0.0014(4) 0.0085(4) 0.0055(4) C2 0.0219(4) 0.0193(4) 0.0223(4) 0.0017(3) 0.0097(3) 0.0039(3) C3 0.0177(4) 0.0186(4) 0.0199(4) 0.0037(3) 0.0070(3) 0.0064(3) C4 0.0153(3) 0.0156(3) 0.0205(4) 0.0036(3) 0.0075(3) 0.0061(3) C5 0.0164(4) 0.0187(4) 0.0198(4) 0.0034(3) 0.0017(3) 0.0081(3) C6 0.0155(3) 0.0216(4) 0.0145(3) 0.0053(3) 0.0020(3) 0.0061(3) C7 0.0176(4) 0.0163(3) 0.0143(3) 0.0038(3) 0.0033(3) 0.0072(3) C8 0.0175(4) 0.0239(4) 0.0157(4) 0.0052(3) 0.0036(3) 0.0071(3) C9 0.0230(4) 0.0274(5) 0.0174(4) 0.0067(3) 0.0066(3) 0.0068(3) C10 0.0270(5) 0.0509(7) 0.0236(5) 0.0129(5) 0.0104(4) 0.0046(5) C11 0.0360(6) 0.0212(4) 0.0444(6) 0.0104(4) 0.0114(5) 0.0164(4) C12 0.0248(4) 0.0170(4) 0.0320(5) 0.0072(3) 0.0118(4) 0.0095(3) C13 0.0185(4) 0.0173(4) 0.0239(4) 0.0055(3) 0.0072(3) 0.0075(3) C14 0.0176(4) 0.0207(4) 0.0173(4) 0.0057(3) 0.0017(3) 0.0065(3) C15 0.0234(4) 0.0235(4) 0.0170(4) 0.0062(3) 0.0007(3) 0.0089(3) C16 0.0282(5) 0.0384(6) 0.0226(5) 0.0119(4) -0.0029(4) 0.0104(4) C17 0.0285(5) 0.0286(5) 0.0160(4) 0.0087(3) 0.0049(3) 0.0089(4) C18 0.0169(4) 0.0272(4) 0.0142(4) 0.0048(3) 0.0016(3) 0.0040(3) C19 0.0149(4) 0.0606(8) 0.0227(5) 0.0091(5) 0.0024(3) 0.0092(4) C20 0.0262(5) 0.0398(6) 0.0164(4) 0.0106(4) 0.0013(3) 0.0064(4) C21 0.0399(6) 0.0268(5) 0.0242(5) -0.0012(4) -0.0033(4) 0.0018(4) C22 0.0295(5) 0.0167(4) 0.0304(5) 0.0019(3) 0.0128(4) 0.0076(3) 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' 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 C5 P1 C6 98.13(4) . . ? C5 P1 C18 102.10(4) . . ? C6 P1 C18 101.56(4) . . ? C4 N1 C5 117.51(7) . . ? C4 N1 H1 111.2(10) . . ? C5 N1 H1 110.7(10) . . ? C6 N2 H2 114.4(10) . . ? C7 N2 C6 119.15(7) . . ? C7 N2 H2 111.8(10) . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? C3 C2 C1 119.85(9) . . ? C3 C2 C22 119.33(9) . . ? C22 C2 C1 120.79(9) . . ? C2 C3 H3 119.7 . . ? C2 C3 C4 120.52(9) . . ? C4 C3 H3 119.7 . . ? C3 C4 N1 118.94(8) . . ? C13 C4 N1 121.71(8) . . ? C13 C4 C3 119.35(8) . . ? P1 C5 H5A 109.8 . . ? P1 C5 H5B 109.8 . . ? N1 C5 P1 109.23(6) . . ? N1 C5 H5A 109.8 . . ? N1 C5 H5B 109.8 . . ? H5A C5 H5B 108.3 . . ? P1 C6 H6A 109.9 . . ? P1 C6 H6B 109.9 . . ? N2 C6 P1 108.91(6) . . ? N2 C6 H6A 109.9 . . ? N2 C6 H6B 109.9 . . ? H6A C6 H6B 108.3 . . ? N2 C7 C14 118.52(8) . . ? C8 C7 N2 122.56(8) . . ? C8 C7 C14 118.91(8) . . ? C7 C8 H8 119.7 . . ? C7 C8 C9 120.64(8) . . ? C9 C8 H8 119.7 . . ? C8 C9 C10 119.72(9) . . ? C17 C9 C8 119.38(9) . . ? C17 C9 C10 120.88(9) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? C12 C11 H11C 109.5 . . ? C13 C12 C11 119.40(10) . . ? C22 C12 C11 121.27(9) . . ? C22 C12 C13 119.33(9) . . ? C4 C13 H13 119.7 . . ? C12 C13 C4 120.58(9) . . ? C12 C13 H13 119.7 . . ? C7 C14 H14 119.5 . . ? C15 C14 C7 120.98(9) . . ? C15 C14 H14 119.5 . . ? C14 C15 C16 120.44(9) . . ? C14 C15 C17 119.23(9) . . ? C17 C15 C16 120.33(9) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C9 C17 C15 120.85(9) . . ? C9 C17 H17 119.6 . . ? C15 C17 H17 119.6 . . ? C19 C18 P1 115.11(7) . . ? C19 C18 C20 109.92(9) . . ? C19 C18 C21 109.22(10) . . ? C20 C18 P1 107.35(7) . . ? C20 C18 C21 108.79(9) . . ? C21 C18 P1 106.25(7) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21B 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C2 C22 H22 119.6 . . ? C12 C22 C2 120.87(9) . . ? C12 C22 H22 119.6 . . ? 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 C5 1.8526(9) . ? P1 C6 1.8556(9) . ? P1 C18 1.8708(9) . ? N1 C4 1.4079(11) . ? N1 C5 1.4631(11) . ? N1 H1 0.845(15) . ? N2 C6 1.4569(11) . ? N2 C7 1.3999(11) . ? N2 H2 0.843(15) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C1 C2 1.5089(15) . ? C2 C3 1.3902(13) . ? C2 C22 1.3974(15) . ? C3 H3 0.9500 . ? C3 C4 1.4006(12) . ? C4 C13 1.3956(12) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.3956(12) . ? C7 C14 1.4025(12) . ? C8 H8 0.9500 . ? C8 C9 1.3972(13) . ? C9 C10 1.5054(15) . ? C9 C17 1.3895(14) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C11 C12 1.5074(14) . ? C12 C13 1.3947(13) . ? C12 C22 1.3906(15) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C14 C15 1.3864(13) . ? C15 C16 1.5083(14) . ? C15 C17 1.3963(14) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17 0.9500 . ? C18 C19 1.5247(14) . ? C18 C20 1.5345(14) . ? C18 C21 1.5399(16) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22 0.9500 . ? 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 N1 C4 C13 C12 179.16(8) . . . . ? N2 C7 C8 C9 179.19(9) . . . . ? N2 C7 C14 C15 -179.21(8) . . . . ? C1 C2 C3 C4 177.64(9) . . . . ? C1 C2 C22 C12 -178.55(9) . . . . ? C2 C3 C4 N1 -179.28(8) . . . . ? C2 C3 C4 C13 1.20(13) . . . . ? C3 C2 C22 C12 -0.76(15) . . . . ? C3 C4 C13 C12 -1.34(13) . . . . ? C4 N1 C5 P1 -170.83(6) . . . . ? C5 P1 C6 N2 -78.49(6) . . . . ? C5 P1 C18 C19 -57.31(9) . . . . ? C5 P1 C18 C20 65.40(8) . . . . ? C5 P1 C18 C21 -178.33(7) . . . . ? C5 N1 C4 C3 156.84(8) . . . . ? C5 N1 C4 C13 -23.65(12) . . . . ? C6 P1 C5 N1 71.72(7) . . . . ? C6 P1 C18 C19 43.72(9) . . . . ? C6 P1 C18 C20 166.44(7) . . . . ? C6 P1 C18 C21 -77.29(8) . . . . ? C6 N2 C7 C8 -9.04(13) . . . . ? C6 N2 C7 C14 171.23(8) . . . . ? C7 N2 C6 P1 178.72(6) . . . . ? C7 C8 C9 C10 -178.09(10) . . . . ? C7 C8 C9 C17 0.43(15) . . . . ? C7 C14 C15 C16 179.22(9) . . . . ? C7 C14 C15 C17 -0.36(14) . . . . ? C8 C7 C14 C15 1.05(14) . . . . ? C8 C9 C17 C15 0.28(16) . . . . ? C10 C9 C17 C15 178.78(10) . . . . ? C11 C12 C13 C4 -179.34(9) . . . . ? C11 C12 C22 C2 -179.61(10) . . . . ? C13 C12 C22 C2 0.63(15) . . . . ? C14 C7 C8 C9 -1.09(14) . . . . ? C14 C15 C17 C9 -0.31(15) . . . . ? C16 C15 C17 C9 -179.89(10) . . . . ? C18 P1 C5 N1 175.47(6) . . . . ? C18 P1 C6 N2 177.31(6) . . . . ? C22 C2 C3 C4 -0.16(14) . . . . ? C22 C12 C13 C4 0.43(14) . . . . ?