# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Radoslaw Starosta' _publ_contact_author_email sta@wchuwr.pl _publ_section_title ; Chalcogenides of the aminomethylphosphines derived from 1-methylpiperazine, 1-ethylpiperazine and morpholine - NMR, DFT and structural studies for determination of electronic and steric properties of the phosphines. ; loop_ _publ_author_name 'Radoslaw Starosta' 'Wojciech Barszczewski' # Attachment '- 5_star14.cif' data_star14 _database_code_depnum_ccdc_archive 'CCDC 767990' #TrackingRef '- 5_star14.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '4,4',4''-phosphoryltris(methylene)tris(1-ethylpiperazine)' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H45 N6 O P' _chemical_formula_sum 'C21 H45 N6 O P' _chemical_formula_weight 428.60 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M 'R 3 c' _symmetry_space_group_name_Hall 'R 3 -2"c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-y, -x, z+1/2' '-x+y, y, z+1/2' 'x, x-y, z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' '-y+2/3, -x+1/3, z+5/6' '-x+y+2/3, y+1/3, z+5/6' 'x+2/3, x-y+1/3, z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-y+1/3, -x+2/3, z+7/6' '-x+y+1/3, y+2/3, z+7/6' 'x+1/3, x-y+2/3, z+7/6' _cell_length_a 20.591(3) _cell_length_b 20.591(3) _cell_length_c 10.134(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3721.1(17) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1650 _cell_measurement_theta_min 3.43 _cell_measurement_theta_max 28.75 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.148 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1416 _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.977 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details 'Oxford Diffraction, CrysAlis 1.171.30' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KM4-CCD _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10526 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.43 _diffrn_reflns_theta_max 28.75 _reflns_number_total 1991 _reflns_number_gt 1455 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, date)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, date)' _computing_data_reduction 'CrysAlis RED ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0740P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(15) _refine_ls_number_reflns 1991 _refine_ls_number_parameters 89 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0625 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1158 _refine_ls_wR_factor_gt 0.1063 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.984 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.3333 0.6667 0.08136(11) 0.0260(2) Uani 1 3 d S . . O1 O 0.3333 0.6667 -0.0617(4) 0.0637(10) Uani 1 3 d S . . C11 C 0.39802(12) 0.64245(13) 0.1601(2) 0.0280(5) Uani 1 1 d . . . H11A H 0.3926 0.6431 0.2551 0.034 Uiso 1 1 calc R . . H11B H 0.3846 0.5918 0.1348 0.034 Uiso 1 1 calc R . . N11 N 0.47643(10) 0.69332(10) 0.12507(17) 0.0263(4) Uani 1 1 d . . . C12 C 0.52708(13) 0.68462(13) 0.2157(2) 0.0303(5) Uani 1 1 d . . . H12A H 0.5176 0.6336 0.2109 0.036 Uiso 1 1 calc R . . H12B H 0.5173 0.6938 0.3053 0.036 Uiso 1 1 calc R . . C13 C 0.60761(13) 0.73805(13) 0.1819(2) 0.0331(5) Uani 1 1 d . . . H13A H 0.6178 0.7892 0.1910 0.040 Uiso 1 1 calc R . . H13B H 0.6399 0.7310 0.2428 0.040 Uiso 1 1 calc R . . N14 N 0.62432(10) 0.72573(11) 0.0455(2) 0.0295(4) Uani 1 1 d . . . C15 C 0.57414(12) 0.73573(13) -0.0432(2) 0.0302(5) Uani 1 1 d . . . H15A H 0.5842 0.7279 -0.1336 0.036 Uiso 1 1 calc R . . H15B H 0.5834 0.7866 -0.0357 0.036 Uiso 1 1 calc R . . C16 C 0.49314(13) 0.68114(14) -0.0101(2) 0.0309(5) Uani 1 1 d . . . H16A H 0.4607 0.6878 -0.0712 0.037 Uiso 1 1 calc R . . H16B H 0.4836 0.6302 -0.0191 0.037 Uiso 1 1 calc R . . C17 C 0.70317(14) 0.77760(14) 0.0130(3) 0.0389(6) Uani 1 1 d . . . H17A H 0.7343 0.7767 0.0840 0.047 Uiso 1 1 calc R . . H17B H 0.7110 0.8280 0.0078 0.047 Uiso 1 1 calc R . . C18 C 0.72810(15) 0.75960(16) -0.1147(3) 0.0509(7) Uani 1 1 d . . . H18A H 0.7140 0.7076 -0.1157 0.076 Uiso 1 1 calc R . . H18B H 0.7816 0.7899 -0.1226 0.076 Uiso 1 1 calc R . . H18C H 0.7046 0.7698 -0.1873 0.076 Uiso 1 1 calc R . . 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 0.0230(3) 0.0230(3) 0.0319(5) 0.000 0.000 0.01151(14) O1 0.0636(15) 0.0636(15) 0.064(3) 0.000 0.000 0.0318(8) C11 0.0269(11) 0.0266(12) 0.0321(13) 0.0038(9) 0.0035(9) 0.0146(9) N11 0.0227(10) 0.0265(9) 0.0289(10) 0.0019(8) -0.0002(8) 0.0117(8) C12 0.0309(12) 0.0328(12) 0.0303(12) 0.0013(9) -0.0035(10) 0.0183(10) C13 0.0306(13) 0.0344(12) 0.0350(13) -0.0044(10) -0.0069(10) 0.0167(11) N14 0.0228(9) 0.0287(10) 0.0374(12) -0.0027(8) 0.0001(8) 0.0131(8) C15 0.0280(12) 0.0315(12) 0.0332(13) -0.0001(10) 0.0025(9) 0.0164(10) C16 0.0266(12) 0.0349(12) 0.0298(13) -0.0032(10) -0.0025(10) 0.0144(10) C17 0.0264(13) 0.0329(13) 0.0549(17) -0.0028(11) -0.0003(11) 0.0128(11) C18 0.0263(13) 0.0476(17) 0.072(2) -0.0041(14) 0.0139(13) 0.0132(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 1.450(4) . ? P1 C11 1.823(2) 2_665 ? P1 C11 1.823(2) 3_565 ? P1 C11 1.823(2) . ? C11 N11 1.462(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? N11 C16 1.464(3) . ? N11 C12 1.466(3) . ? C12 C13 1.501(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 N14 1.477(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? N14 C15 1.459(3) . ? N14 C17 1.466(3) . ? C15 C16 1.511(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.506(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 C11 115.95(8) . 2_665 ? O1 P1 C11 115.95(8) . 3_565 ? C11 P1 C11 102.29(10) 2_665 3_565 ? O1 P1 C11 115.95(8) . . ? C11 P1 C11 102.29(10) 2_665 . ? C11 P1 C11 102.29(10) 3_565 . ? N11 C11 P1 113.19(15) . . ? N11 C11 H11A 108.9 . . ? P1 C11 H11A 108.9 . . ? N11 C11 H11B 108.9 . . ? P1 C11 H11B 108.9 . . ? H11A C11 H11B 107.8 . . ? C11 N11 C16 111.97(17) . . ? C11 N11 C12 111.01(17) . . ? C16 N11 C12 108.80(18) . . ? N11 C12 C13 111.12(18) . . ? N11 C12 H12A 109.4 . . ? C13 C12 H12A 109.4 . . ? N11 C12 H12B 109.4 . . ? C13 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? N14 C13 C12 110.76(19) . . ? N14 C13 H13A 109.5 . . ? C12 C13 H13A 109.5 . . ? N14 C13 H13B 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? C15 N14 C17 111.31(19) . . ? C15 N14 C13 108.05(17) . . ? C17 N14 C13 110.66(19) . . ? N14 C15 C16 110.76(18) . . ? N14 C15 H15A 109.5 . . ? C16 C15 H15A 109.5 . . ? N14 C15 H15B 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? N11 C16 C15 110.30(19) . . ? N11 C16 H16A 109.6 . . ? C15 C16 H16A 109.6 . . ? N11 C16 H16B 109.6 . . ? C15 C16 H16B 109.6 . . ? H16A C16 H16B 108.1 . . ? N14 C17 C18 113.8(2) . . ? N14 C17 H17A 108.8 . . ? C18 C17 H17A 108.8 . . ? N14 C17 H17B 108.8 . . ? C18 C17 H17B 108.8 . . ? H17A C17 H17B 107.7 . . ? 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_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 C11 N11 59.86(17) . . . . ? C11 P1 C11 N11 -67.3(2) 2_665 . . . ? C11 P1 C11 N11 -172.98(14) 3_565 . . . ? P1 C11 N11 C16 -73.4(2) . . . . ? P1 C11 N11 C12 164.77(16) . . . . ? C11 N11 C12 C13 -178.67(19) . . . . ? C16 N11 C12 C13 57.7(2) . . . . ? N11 C12 C13 N14 -58.8(2) . . . . ? C12 C13 N14 C15 58.3(2) . . . . ? C12 C13 N14 C17 -179.6(2) . . . . ? C17 N14 C15 C16 179.1(2) . . . . ? C13 N14 C15 C16 -59.2(2) . . . . ? C11 N11 C16 C15 178.88(19) . . . . ? C12 N11 C16 C15 -58.0(2) . . . . ? N14 C15 C16 N11 60.6(2) . . . . ? C15 N14 C17 C18 -70.2(3) . . . . ? C13 N14 C17 C18 169.6(2) . . . . ? 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 C16 H16A O1 0.97 2.44 3.195(3) 135 . C11 H11A O1 0.97 2.40 3.261(4) 148 4_665 _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.251 _refine_diff_density_min -0.480 _refine_diff_density_rms 0.053 # start Validation Reply Form _vrf_PLAT230_ALERT_2_B ; PROBLEM: _Hirshfeld Test Diff for P1 -- O1 .. 16.05 su RESPONSE: this is the most probably caused by a certain disorder around O1 atom, resulting from the short contacts with six hydrogen atoms around oxygen atom atop the three-fold axis ; _vrf_PLAT242_ALERT_2_C ; PROBLEM: Check Low Ueq as Compared to Neighbors for P1 RESPONSE: this is the most probably caused by a certain disorder around O1 atom... ; # end Validation Reply Form # Attachment '- 6_star12dc.cif' data_star12dc _database_code_depnum_ccdc_archive 'CCDC 767991' #TrackingRef '- 6_star12dc.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '4,4',4''-phosphoryltris(methylene)trimorpholine' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H30 N3 O4 P' _chemical_formula_sum 'C15 H30 N3 O4 P' _chemical_formula_weight 347.39 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.168(3) _cell_length_b 16.493(3) _cell_length_c 9.919(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.96(2) _cell_angle_gamma 90.00 _cell_volume 1822.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3150 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 25.08 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.173 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.567 _exptl_absorpt_correction_T_max 0.789 _exptl_absorpt_process_details 'Oxford Diffraction, CrysAlis 1.171.30' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KM4-CCD _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17280 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.08 _reflns_number_total 3223 _reflns_number_gt 2529 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, date)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, date)' _computing_data_reduction 'CrysAlis RED ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0372P)^2^+0.4381P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3223 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0773 _refine_ls_wR_factor_gt 0.0715 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.50027(4) 0.71059(2) 0.24279(4) 0.01483(11) Uani 1 1 d . . . O1 O 0.50894(9) 0.69503(6) 0.09592(10) 0.0196(3) Uani 1 1 d . . . C11 C 0.42702(14) 0.63015(9) 0.33394(15) 0.0180(3) Uani 1 1 d . . . H11A H 0.4892 0.5968 0.3835 0.022 Uiso 1 1 calc R . . H11B H 0.3768 0.6550 0.4012 0.022 Uiso 1 1 calc R . . N11 N 0.35189(11) 0.57775(7) 0.24424(12) 0.0169(3) Uani 1 1 d . . . C12 C 0.42468(15) 0.51476(9) 0.18556(16) 0.0204(4) Uani 1 1 d . . . H12A H 0.4660 0.4823 0.2588 0.025 Uiso 1 1 calc R . . H12B H 0.4866 0.5403 0.1327 0.025 Uiso 1 1 calc R . . C13 C 0.34649(15) 0.46004(10) 0.09486(16) 0.0238(4) Uani 1 1 d . . . H13A H 0.3097 0.4921 0.0184 0.029 Uiso 1 1 calc R . . H13B H 0.3967 0.4173 0.0573 0.029 Uiso 1 1 calc R . . O14 O 0.25416(10) 0.42317(6) 0.16597(11) 0.0259(3) Uani 1 1 d . . . C15 C 0.18222(15) 0.48427(10) 0.22276(18) 0.0253(4) Uani 1 1 d . . . H15A H 0.1192 0.4581 0.2732 0.030 Uiso 1 1 calc R . . H15B H 0.1421 0.5169 0.1491 0.030 Uiso 1 1 calc R . . C16 C 0.25699(15) 0.53936(10) 0.31693(16) 0.0218(4) Uani 1 1 d . . . H16A H 0.2051 0.5816 0.3533 0.026 Uiso 1 1 calc R . . H16B H 0.2933 0.5075 0.3938 0.026 Uiso 1 1 calc R . . C21 C 0.64274(14) 0.72576(9) 0.33898(15) 0.0177(3) Uani 1 1 d . . . H21A H 0.6782 0.7778 0.3121 0.021 Uiso 1 1 calc R . . H21B H 0.6289 0.7290 0.4364 0.021 Uiso 1 1 calc R . . N21 N 0.72722(11) 0.65989(7) 0.31708(12) 0.0162(3) Uani 1 1 d . . . C22 C 0.81480(15) 0.65122(10) 0.43329(16) 0.0223(4) Uani 1 1 d . . . H22A H 0.7725 0.6392 0.5155 0.027 Uiso 1 1 calc R . . H22B H 0.8594 0.7027 0.4483 0.027 Uiso 1 1 calc R . . C23 C 0.90162(16) 0.58347(11) 0.40798(17) 0.0279(4) Uani 1 1 d . . . H23A H 0.9602 0.5780 0.4870 0.033 Uiso 1 1 calc R . . H23B H 0.8570 0.5317 0.3970 0.033 Uiso 1 1 calc R . . O24 O 0.96413(10) 0.59868(7) 0.28993(12) 0.0282(3) Uani 1 1 d . . . C25 C 0.87994(15) 0.60721(10) 0.17598(17) 0.0257(4) Uani 1 1 d . . . H25A H 0.8353 0.5558 0.1612 0.031 Uiso 1 1 calc R . . H25B H 0.9236 0.6183 0.0944 0.031 Uiso 1 1 calc R . . C26 C 0.79216(15) 0.67514(10) 0.19576(16) 0.0205(4) Uani 1 1 d . . . H26A H 0.8359 0.7273 0.2055 0.025 Uiso 1 1 calc R . . H26B H 0.7344 0.6790 0.1157 0.025 Uiso 1 1 calc R . . C31 C 0.42087(14) 0.80285(9) 0.28233(15) 0.0176(3) Uani 1 1 d . . . H31A H 0.4497 0.8207 0.3742 0.021 Uiso 1 1 calc R . . H31B H 0.4423 0.8456 0.2183 0.021 Uiso 1 1 calc R . . N31 N 0.29024(11) 0.79636(8) 0.27717(12) 0.0172(3) Uani 1 1 d . . . C32 C 0.23786(15) 0.78907(12) 0.13891(17) 0.0301(4) Uani 1 1 d . . . H32A H 0.2691 0.7398 0.0965 0.036 Uiso 1 1 calc R . . H32B H 0.2606 0.8366 0.0855 0.036 Uiso 1 1 calc R . . C33 C 0.10296(17) 0.78410(13) 0.1391(2) 0.0451(6) Uani 1 1 d . . . H33A H 0.0681 0.7785 0.0451 0.054 Uiso 1 1 calc R . . H33B H 0.0806 0.7354 0.1901 0.054 Uiso 1 1 calc R . . O34 O 0.05469(11) 0.85468(8) 0.19906(12) 0.0330(3) Uani 1 1 d . . . C35 C 0.10467(16) 0.86271(11) 0.33430(17) 0.0295(4) Uani 1 1 d . . . H35A H 0.0810 0.8155 0.3880 0.035 Uiso 1 1 calc R . . H35B H 0.0722 0.9121 0.3752 0.035 Uiso 1 1 calc R . . C36 C 0.23957(15) 0.86805(10) 0.33944(16) 0.0223(4) Uani 1 1 d . . . H36A H 0.2635 0.9174 0.2911 0.027 Uiso 1 1 calc R . . H36B H 0.2719 0.8724 0.4347 0.027 Uiso 1 1 calc R . . 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 0.0125(2) 0.0149(2) 0.0169(2) 0.00004(16) 0.00020(15) -0.00045(17) O1 0.0179(6) 0.0240(6) 0.0171(6) -0.0007(4) 0.0015(5) -0.0014(5) C11 0.0180(9) 0.0175(8) 0.0186(8) -0.0004(6) 0.0019(7) -0.0005(7) N11 0.0134(7) 0.0158(7) 0.0218(7) -0.0016(5) 0.0034(5) -0.0008(5) C12 0.0178(9) 0.0167(8) 0.0271(9) -0.0012(6) 0.0045(7) 0.0026(7) C13 0.0264(10) 0.0183(8) 0.0269(9) -0.0015(7) 0.0030(7) 0.0013(7) O14 0.0257(7) 0.0161(6) 0.0363(7) -0.0027(5) 0.0039(5) -0.0033(5) C15 0.0183(9) 0.0226(9) 0.0352(10) -0.0010(7) 0.0040(8) -0.0027(7) C16 0.0184(9) 0.0209(8) 0.0268(9) 0.0002(7) 0.0060(7) -0.0011(7) C21 0.0158(9) 0.0180(8) 0.0190(8) -0.0019(6) 0.0001(7) -0.0004(6) N21 0.0130(7) 0.0180(7) 0.0174(7) -0.0011(5) -0.0005(5) 0.0018(5) C22 0.0208(9) 0.0242(9) 0.0212(8) -0.0010(7) -0.0038(7) 0.0022(7) C23 0.0242(10) 0.0284(10) 0.0303(10) -0.0012(7) -0.0039(8) 0.0063(8) O24 0.0164(6) 0.0333(7) 0.0348(7) -0.0044(5) 0.0001(5) 0.0065(5) C25 0.0209(9) 0.0281(9) 0.0280(9) -0.0053(7) 0.0019(7) 0.0017(8) C26 0.0173(9) 0.0229(8) 0.0215(8) -0.0010(7) 0.0022(7) 0.0003(7) C31 0.0165(9) 0.0154(8) 0.0203(8) -0.0005(6) -0.0020(6) 0.0001(7) N31 0.0144(7) 0.0168(7) 0.0201(7) -0.0020(5) 0.0006(5) 0.0022(6) C32 0.0216(10) 0.0407(11) 0.0270(9) -0.0155(8) -0.0055(7) 0.0114(8) C33 0.0222(11) 0.0493(13) 0.0616(14) -0.0305(11) -0.0135(9) 0.0133(9) O34 0.0210(7) 0.0399(7) 0.0372(7) -0.0081(6) -0.0040(5) 0.0123(6) C35 0.0291(11) 0.0325(10) 0.0277(9) 0.0040(8) 0.0071(8) 0.0114(8) C36 0.0259(10) 0.0201(8) 0.0206(8) -0.0026(7) 0.0005(7) 0.0077(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 1.4889(11) . ? P1 C21 1.8152(16) . ? P1 C31 1.8175(16) . ? P1 C11 1.8301(16) . ? C11 N11 1.4626(19) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? N11 C12 1.464(2) . ? N11 C16 1.466(2) . ? C12 C13 1.509(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 O14 1.425(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? O14 C15 1.429(2) . ? C15 C16 1.513(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C21 N21 1.4649(19) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? N21 C22 1.4664(19) . ? N21 C26 1.469(2) . ? C22 C23 1.512(2) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 O24 1.426(2) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? O24 C25 1.426(2) . ? C25 C26 1.511(2) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C31 N31 1.460(2) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? N31 C32 1.458(2) . ? N31 C36 1.4656(19) . ? C32 C33 1.509(3) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 O34 1.430(2) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? O34 C35 1.423(2) . ? C35 C36 1.506(2) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? 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 C21 115.10(7) . . ? O1 P1 C31 114.91(7) . . ? C21 P1 C31 101.20(7) . . ? O1 P1 C11 114.83(7) . . ? C21 P1 C11 104.22(7) . . ? C31 P1 C11 105.01(8) . . ? N11 C11 P1 112.64(10) . . ? N11 C11 H11A 109.1 . . ? P1 C11 H11A 109.1 . . ? N11 C11 H11B 109.1 . . ? P1 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? C11 N11 C12 110.49(12) . . ? C11 N11 C16 111.09(12) . . ? C12 N11 C16 109.22(12) . . ? N11 C12 C13 110.30(13) . . ? N11 C12 H12A 109.6 . . ? C13 C12 H12A 109.6 . . ? N11 C12 H12B 109.6 . . ? C13 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? O14 C13 C12 111.64(13) . . ? O14 C13 H13A 109.3 . . ? C12 C13 H13A 109.3 . . ? O14 C13 H13B 109.3 . . ? C12 C13 H13B 109.3 . . ? H13A C13 H13B 108.0 . . ? C13 O14 C15 109.88(12) . . ? O14 C15 C16 111.45(14) . . ? O14 C15 H15A 109.3 . . ? C16 C15 H15A 109.3 . . ? O14 C15 H15B 109.3 . . ? C16 C15 H15B 109.3 . . ? H15A C15 H15B 108.0 . . ? N11 C16 C15 110.05(13) . . ? N11 C16 H16A 109.7 . . ? C15 C16 H16A 109.7 . . ? N11 C16 H16B 109.7 . . ? C15 C16 H16B 109.7 . . ? H16A C16 H16B 108.2 . . ? N21 C21 P1 111.72(10) . . ? N21 C21 H21A 109.3 . . ? P1 C21 H21A 109.3 . . ? N21 C21 H21B 109.3 . . ? P1 C21 H21B 109.3 . . ? H21A C21 H21B 107.9 . . ? C21 N21 C22 110.93(11) . . ? C21 N21 C26 110.73(12) . . ? C22 N21 C26 108.69(13) . . ? N21 C22 C23 110.01(13) . . ? N21 C22 H22A 109.7 . . ? C23 C22 H22A 109.7 . . ? N21 C22 H22B 109.7 . . ? C23 C22 H22B 109.7 . . ? H22A C22 H22B 108.2 . . ? O24 C23 C22 111.24(14) . . ? O24 C23 H23A 109.4 . . ? C22 C23 H23A 109.4 . . ? O24 C23 H23B 109.4 . . ? C22 C23 H23B 109.4 . . ? H23A C23 H23B 108.0 . . ? C23 O24 C25 109.55(13) . . ? O24 C25 C26 111.62(13) . . ? O24 C25 H25A 109.3 . . ? C26 C25 H25A 109.3 . . ? O24 C25 H25B 109.3 . . ? C26 C25 H25B 109.3 . . ? H25A C25 H25B 108.0 . . ? N21 C26 C25 109.93(13) . . ? N21 C26 H26A 109.7 . . ? C25 C26 H26A 109.7 . . ? N21 C26 H26B 109.7 . . ? C25 C26 H26B 109.7 . . ? H26A C26 H26B 108.2 . . ? N31 C31 P1 115.61(10) . . ? N31 C31 H31A 108.4 . . ? P1 C31 H31A 108.4 . . ? N31 C31 H31B 108.4 . . ? P1 C31 H31B 108.4 . . ? H31A C31 H31B 107.4 . . ? C32 N31 C31 111.96(13) . . ? C32 N31 C36 108.75(12) . . ? C31 N31 C36 109.88(12) . . ? N31 C32 C33 109.82(15) . . ? N31 C32 H32A 109.7 . . ? C33 C32 H32A 109.7 . . ? N31 C32 H32B 109.7 . . ? C33 C32 H32B 109.7 . . ? H32A C32 H32B 108.2 . . ? O34 C33 C32 111.19(15) . . ? O34 C33 H33A 109.4 . . ? C32 C33 H33A 109.4 . . ? O34 C33 H33B 109.4 . . ? C32 C33 H33B 109.4 . . ? H33A C33 H33B 108.0 . . ? C35 O34 C33 109.47(13) . . ? O34 C35 C36 111.32(14) . . ? O34 C35 H35A 109.4 . . ? C36 C35 H35A 109.4 . . ? O34 C35 H35B 109.4 . . ? C36 C35 H35B 109.4 . . ? H35A C35 H35B 108.0 . . ? N31 C36 C35 110.66(14) . . ? N31 C36 H36A 109.5 . . ? C35 C36 H36A 109.5 . . ? N31 C36 H36B 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 108.1 . . ? 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 C11 N11 -20.35(13) . . . . ? C21 P1 C11 N11 -147.18(11) . . . . ? C31 P1 C11 N11 106.84(11) . . . . ? P1 C11 N11 C12 83.61(14) . . . . ? P1 C11 N11 C16 -155.01(11) . . . . ? C11 N11 C12 C13 179.09(13) . . . . ? C16 N11 C12 C13 56.61(16) . . . . ? N11 C12 C13 O14 -57.97(17) . . . . ? C12 C13 O14 C15 57.93(17) . . . . ? C13 O14 C15 C16 -58.10(17) . . . . ? C11 N11 C16 C15 -178.86(13) . . . . ? C12 N11 C16 C15 -56.74(16) . . . . ? O14 C15 C16 N11 58.25(18) . . . . ? O1 P1 C21 N21 -52.17(13) . . . . ? C31 P1 C21 N21 -176.70(11) . . . . ? C11 P1 C21 N21 74.49(12) . . . . ? P1 C21 N21 C22 -154.08(11) . . . . ? P1 C21 N21 C26 85.14(13) . . . . ? C21 N21 C22 C23 -179.51(13) . . . . ? C26 N21 C22 C23 -57.54(17) . . . . ? N21 C22 C23 O24 59.17(18) . . . . ? C22 C23 O24 C25 -58.59(17) . . . . ? C23 O24 C25 C26 58.45(17) . . . . ? C21 N21 C26 C25 179.23(12) . . . . ? C22 N21 C26 C25 57.14(16) . . . . ? O24 C25 C26 N21 -58.55(17) . . . . ? O1 P1 C31 N31 83.22(12) . . . . ? C21 P1 C31 N31 -152.13(11) . . . . ? C11 P1 C31 N31 -43.92(13) . . . . ? P1 C31 N31 C32 -71.62(15) . . . . ? P1 C31 N31 C36 167.43(10) . . . . ? C31 N31 C32 C33 -178.98(14) . . . . ? C36 N31 C32 C33 -57.37(19) . . . . ? N31 C32 C33 O34 59.7(2) . . . . ? C32 C33 O34 C35 -59.1(2) . . . . ? C33 O34 C35 C36 58.08(19) . . . . ? C32 N31 C36 C35 56.79(17) . . . . ? C31 N31 C36 C35 179.65(13) . . . . ? O34 C35 C36 N31 -57.92(18) . . . . ? 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 C12 H12B O1 0.99 2.59 3.261(2) 125 . C26 H26B O1 0.99 2.53 3.266(2) 132 . C21 H21A O14 0.99 2.52 3.455(2) 158 2_655 C21 H21B O1 0.99 2.48 3.311(2) 141 4_576 C23 H23A O34 0.99 2.54 3.4083(17) 146 4_676 C31 H31A O1 0.99 2.27 3.197(2) 156 4_576 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.327 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.041 # Attachment '- 9_star7dc.cif' data_star7dc _database_code_depnum_ccdc_archive 'CCDC 767992' #TrackingRef '- 9_star7dc.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '4,4',4''-phosphorothioyltris(methylene)trimorpholine' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H30 N3 O3 P S' _chemical_formula_sum 'C15 H30 N3 O3 P S' _chemical_formula_weight 363.46 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_space_group_name_Hall 'C -2yc' loop_ _symmetry_equiv_pos_as_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' _cell_length_a 6.117(3) _cell_length_b 19.103(2) _cell_length_c 15.751(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.22(3) _cell_angle_gamma 90.00 _cell_volume 1840.1(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5150 _cell_measurement_theta_min 3.35 _cell_measurement_theta_max 36.81 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.280 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.967 _exptl_absorpt_correction_T_max 0.972 _exptl_absorpt_process_details 'Oxford Diffraction, CrysAlis 1.171.30' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KM4-CCD _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10015 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0390 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 36.81 _reflns_number_total 5318 _reflns_number_gt 4462 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, date)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, date)' _computing_data_reduction 'CrysAlis RED ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0437P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.06(5) _refine_ls_number_reflns 5318 _refine_ls_number_parameters 208 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0429 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0747 _refine_ls_wR_factor_gt 0.0710 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.60599(5) 0.22633(2) 0.06961(3) 0.01891(10) Uani 1 1 d . . . P1 P 0.28638(5) 0.228357(19) 0.06508(3) 0.01341(9) Uani 1 1 d . . . C11 C 0.1588(3) 0.22492(8) 0.16850(10) 0.0158(3) Uani 1 1 d . . . H11A H 0.2186 0.2628 0.2051 0.019 Uiso 1 1 calc R . . H11B H -0.0007 0.2324 0.1614 0.019 Uiso 1 1 calc R . . N11 N 0.1990(2) 0.15722(7) 0.20928(9) 0.0160(3) Uani 1 1 d . . . C12 C 0.0021(3) 0.12797(8) 0.24640(11) 0.0198(3) Uani 1 1 d . . . H12B H -0.1147 0.1237 0.2022 0.024 Uiso 1 1 calc R . . H12A H -0.0507 0.1595 0.2915 0.024 Uiso 1 1 calc R . . C13 C 0.0538(3) 0.05659(9) 0.28350(12) 0.0232(4) Uani 1 1 d . . . H13B H -0.0793 0.0369 0.3091 0.028 Uiso 1 1 calc R . . H13A H 0.0993 0.0247 0.2376 0.028 Uiso 1 1 calc R . . O14 O 0.2235(2) 0.06093(6) 0.34650(8) 0.0236(3) Uani 1 1 d . . . C15 C 0.4155(3) 0.08835(10) 0.30895(12) 0.0241(4) Uani 1 1 d . . . H15A H 0.4623 0.0567 0.2630 0.029 Uiso 1 1 calc R . . H15B H 0.5350 0.0905 0.3523 0.029 Uiso 1 1 calc R . . C16 C 0.3751(3) 0.16067(9) 0.27301(12) 0.0221(4) Uani 1 1 d . . . H16A H 0.3345 0.1931 0.3191 0.027 Uiso 1 1 calc R . . H16B H 0.5100 0.1785 0.2469 0.027 Uiso 1 1 calc R . . C21 C 0.1601(3) 0.15572(8) 0.00742(10) 0.0162(3) Uani 1 1 d . . . H21A H 0.2041 0.1110 0.0345 0.019 Uiso 1 1 calc R . . H21B H -0.0010 0.1597 0.0099 0.019 Uiso 1 1 calc R . . N21 N 0.2267(2) 0.15596(7) -0.08128(9) 0.0159(3) Uani 1 1 d . . . C22 C 0.4068(3) 0.10702(9) -0.09598(11) 0.0193(3) Uani 1 1 d . . . H22A H 0.3588 0.0585 -0.0844 0.023 Uiso 1 1 calc R . . H22B H 0.5318 0.1181 -0.0573 0.023 Uiso 1 1 calc R . . C23 C 0.4759(3) 0.11325(10) -0.18699(12) 0.0237(4) Uani 1 1 d . . . H23A H 0.5317 0.1611 -0.1969 0.028 Uiso 1 1 calc R . . H23B H 0.5966 0.0800 -0.1971 0.028 Uiso 1 1 calc R . . O24 O 0.3012(2) 0.09928(7) -0.24548(8) 0.0252(3) Uani 1 1 d . . . C25 C 0.1237(3) 0.14579(10) -0.23054(11) 0.0263(4) Uani 1 1 d . . . H25B H 0.0009 0.1347 -0.2702 0.032 Uiso 1 1 calc R . . H25A H 0.1704 0.1945 -0.2415 0.032 Uiso 1 1 calc R . . C26 C 0.0471(3) 0.13973(9) -0.13998(12) 0.0208(3) Uani 1 1 d . . . H26B H -0.0754 0.1726 -0.1309 0.025 Uiso 1 1 calc R . . H26A H -0.0059 0.0916 -0.1295 0.025 Uiso 1 1 calc R . . C31 C 0.1618(3) 0.30537(8) 0.01571(11) 0.0173(3) Uani 1 1 d . . . H31A H 0.1963 0.3060 -0.0454 0.021 Uiso 1 1 calc R . . H31B H 0.0009 0.3024 0.0204 0.021 Uiso 1 1 calc R . . N31 N 0.2391(2) 0.37070(6) 0.05525(10) 0.0164(3) Uani 1 1 d . . . C32 C 0.4199(3) 0.40011(8) 0.00765(11) 0.0186(3) Uani 1 1 d . . . H32A H 0.3709 0.4094 -0.0516 0.022 Uiso 1 1 calc R . . H32B H 0.5416 0.3660 0.0064 0.022 Uiso 1 1 calc R . . C33 C 0.4989(3) 0.46759(8) 0.04851(12) 0.0224(4) Uani 1 1 d . . . H33A H 0.5581 0.4574 0.1062 0.027 Uiso 1 1 calc R . . H33B H 0.6187 0.4874 0.0147 0.027 Uiso 1 1 calc R . . O34 O 0.3288(2) 0.51760(6) 0.05417(9) 0.0276(3) Uani 1 1 d . . . C35 C 0.1529(3) 0.48921(9) 0.10112(12) 0.0242(4) Uani 1 1 d . . . H35B H 0.0339 0.5242 0.1038 0.029 Uiso 1 1 calc R . . H35A H 0.2044 0.4794 0.1599 0.029 Uiso 1 1 calc R . . C36 C 0.0641(3) 0.42255(8) 0.06176(12) 0.0203(3) Uani 1 1 d . . . H36B H -0.0541 0.4037 0.0971 0.024 Uiso 1 1 calc R . . H36A H 0.0018 0.4327 0.0045 0.024 Uiso 1 1 calc R . . 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 S1 0.01157(19) 0.0230(2) 0.0222(2) -0.00178(17) 0.00031(16) -0.00007(15) P1 0.01163(18) 0.01461(17) 0.0140(2) -0.00073(17) 0.00012(15) -0.00101(15) C11 0.0151(7) 0.0180(6) 0.0142(8) -0.0004(6) 0.0002(6) 0.0021(5) N11 0.0139(6) 0.0202(6) 0.0140(7) 0.0033(5) -0.0009(5) 0.0018(5) C12 0.0160(8) 0.0220(7) 0.0215(9) 0.0013(6) 0.0012(7) 0.0009(6) C13 0.0259(9) 0.0225(7) 0.0214(9) 0.0013(7) 0.0017(7) -0.0020(6) O14 0.0272(7) 0.0265(6) 0.0171(6) 0.0035(5) 0.0015(5) 0.0037(5) C15 0.0191(8) 0.0342(9) 0.0189(10) 0.0024(7) -0.0026(7) 0.0044(7) C16 0.0168(8) 0.0296(8) 0.0198(9) 0.0025(7) -0.0024(7) 0.0004(6) C21 0.0164(7) 0.0157(6) 0.0167(8) -0.0029(6) 0.0014(6) -0.0048(5) N21 0.0159(6) 0.0176(6) 0.0141(7) -0.0014(5) 0.0012(5) -0.0008(5) C22 0.0185(8) 0.0204(7) 0.0190(9) -0.0015(6) 0.0014(7) 0.0009(6) C23 0.0213(9) 0.0305(8) 0.0197(10) -0.0055(8) 0.0061(7) -0.0031(7) O24 0.0268(7) 0.0316(6) 0.0172(6) -0.0054(5) 0.0018(5) -0.0006(5) C25 0.0300(10) 0.0315(9) 0.0172(9) 0.0004(7) -0.0051(8) 0.0031(7) C26 0.0185(8) 0.0233(7) 0.0207(9) -0.0024(7) -0.0019(7) 0.0017(6) C31 0.0145(7) 0.0169(7) 0.0204(9) 0.0024(6) -0.0029(6) -0.0034(5) N31 0.0142(6) 0.0147(5) 0.0204(7) -0.0008(5) 0.0020(6) -0.0011(4) C32 0.0163(7) 0.0175(7) 0.0220(9) -0.0004(6) 0.0054(6) -0.0013(5) C33 0.0189(9) 0.0188(7) 0.0298(11) -0.0023(7) 0.0031(7) -0.0031(6) O34 0.0252(7) 0.0185(5) 0.0394(9) 0.0004(5) 0.0062(6) 0.0007(5) C35 0.0255(9) 0.0220(8) 0.0253(10) -0.0044(7) 0.0035(7) 0.0053(6) C36 0.0168(8) 0.0255(7) 0.0188(9) 0.0005(7) 0.0049(7) 0.0025(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 S1 P1 1.9553(11) . ? P1 C21 1.8213(16) . ? P1 C11 1.8223(17) . ? P1 C31 1.8234(16) . ? C11 N11 1.4624(19) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? N11 C16 1.458(2) . ? N11 C12 1.461(2) . ? C12 C13 1.514(2) . ? C12 H12B 0.9900 . ? C12 H12A 0.9900 . ? C13 O14 1.423(2) . ? C13 H13B 0.9900 . ? C13 H13A 0.9900 . ? O14 C15 1.426(2) . ? C15 C16 1.511(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C21 N21 1.464(2) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? N21 C26 1.454(2) . ? N21 C22 1.467(2) . ? C22 C23 1.508(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 O24 1.421(2) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? O24 C25 1.427(2) . ? C25 C26 1.515(3) . ? C25 H25B 0.9900 . ? C25 H25A 0.9900 . ? C26 H26B 0.9900 . ? C26 H26A 0.9900 . ? C31 N31 1.469(2) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? N31 C32 1.462(2) . ? N31 C36 1.464(2) . ? C32 C33 1.515(2) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 O34 1.417(2) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? O34 C35 1.426(2) . ? C35 C36 1.512(2) . ? C35 H35B 0.9900 . ? C35 H35A 0.9900 . ? C36 H36B 0.9900 . ? C36 H36A 0.9900 . ? 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 C21 P1 C11 103.48(7) . . ? C21 P1 C31 103.47(8) . . ? C11 P1 C31 103.13(7) . . ? C21 P1 S1 114.60(6) . . ? C11 P1 S1 114.43(6) . . ? C31 P1 S1 116.11(6) . . ? N11 C11 P1 110.69(10) . . ? N11 C11 H11A 109.5 . . ? P1 C11 H11A 109.5 . . ? N11 C11 H11B 109.5 . . ? P1 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C16 N11 C12 110.20(14) . . ? C16 N11 C11 112.16(13) . . ? C12 N11 C11 112.43(12) . . ? N11 C12 C13 109.36(13) . . ? N11 C12 H12B 109.8 . . ? C13 C12 H12B 109.8 . . ? N11 C12 H12A 109.8 . . ? C13 C12 H12A 109.8 . . ? H12B C12 H12A 108.2 . . ? O14 C13 C12 111.09(14) . . ? O14 C13 H13B 109.4 . . ? C12 C13 H13B 109.4 . . ? O14 C13 H13A 109.4 . . ? C12 C13 H13A 109.4 . . ? H13B C13 H13A 108.0 . . ? C13 O14 C15 109.12(14) . . ? O14 C15 C16 111.20(15) . . ? O14 C15 H15A 109.4 . . ? C16 C15 H15A 109.4 . . ? O14 C15 H15B 109.4 . . ? C16 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? N11 C16 C15 109.21(15) . . ? N11 C16 H16A 109.8 . . ? C15 C16 H16A 109.8 . . ? N11 C16 H16B 109.8 . . ? C15 C16 H16B 109.8 . . ? H16A C16 H16B 108.3 . . ? N21 C21 P1 110.48(10) . . ? N21 C21 H21A 109.6 . . ? P1 C21 H21A 109.6 . . ? N21 C21 H21B 109.6 . . ? P1 C21 H21B 109.6 . . ? H21A C21 H21B 108.1 . . ? C26 N21 C21 112.61(13) . . ? C26 N21 C22 108.88(13) . . ? C21 N21 C22 111.96(13) . . ? N21 C22 C23 109.05(15) . . ? N21 C22 H22A 109.9 . . ? C23 C22 H22A 109.9 . . ? N21 C22 H22B 109.9 . . ? C23 C22 H22B 109.9 . . ? H22A C22 H22B 108.3 . . ? O24 C23 C22 112.30(14) . . ? O24 C23 H23A 109.1 . . ? C22 C23 H23A 109.1 . . ? O24 C23 H23B 109.1 . . ? C22 C23 H23B 109.1 . . ? H23A C23 H23B 107.9 . . ? C23 O24 C25 109.92(13) . . ? O24 C25 C26 111.06(15) . . ? O24 C25 H25B 109.4 . . ? C26 C25 H25B 109.4 . . ? O24 C25 H25A 109.4 . . ? C26 C25 H25A 109.4 . . ? H25B C25 H25A 108.0 . . ? N21 C26 C25 109.76(15) . . ? N21 C26 H26B 109.7 . . ? C25 C26 H26B 109.7 . . ? N21 C26 H26A 109.7 . . ? C25 C26 H26A 109.7 . . ? H26B C26 H26A 108.2 . . ? N31 C31 P1 112.14(11) . . ? N31 C31 H31A 109.2 . . ? P1 C31 H31A 109.2 . . ? N31 C31 H31B 109.2 . . ? P1 C31 H31B 109.2 . . ? H31A C31 H31B 107.9 . . ? C32 N31 C36 109.79(12) . . ? C32 N31 C31 110.45(13) . . ? C36 N31 C31 112.04(13) . . ? N31 C32 C33 110.31(14) . . ? N31 C32 H32A 109.6 . . ? C33 C32 H32A 109.6 . . ? N31 C32 H32B 109.6 . . ? C33 C32 H32B 109.6 . . ? H32A C32 H32B 108.1 . . ? O34 C33 C32 111.84(14) . . ? O34 C33 H33A 109.2 . . ? C32 C33 H33A 109.2 . . ? O34 C33 H33B 109.2 . . ? C32 C33 H33B 109.2 . . ? H33A C33 H33B 107.9 . . ? C33 O34 C35 109.86(12) . . ? O34 C35 C36 112.09(14) . . ? O34 C35 H35B 109.2 . . ? C36 C35 H35B 109.2 . . ? O34 C35 H35A 109.2 . . ? C36 C35 H35A 109.2 . . ? H35B C35 H35A 107.9 . . ? N31 C36 C35 109.97(14) . . ? N31 C36 H36B 109.7 . . ? C35 C36 H36B 109.7 . . ? N31 C36 H36A 109.7 . . ? C35 C36 H36A 109.7 . . ? H36B C36 H36A 108.2 . . ? 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 C32 H32B S1 0.99 2.87 3.636(2) 135 . C11 H11B S1 0.99 2.78 3.693(3) 153 1_455 _diffrn_measured_fraction_theta_max 0.699 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.456 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.058 # Attachment '- 12_star11dc.cif' data_star11dc _database_code_depnum_ccdc_archive 'CCDC 767993' #TrackingRef '- 12_star11dc.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '4,4',4''-phosphoroselenoyltris(methylene)trimorpholine ' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H30 N3 O3 P Se' _chemical_formula_sum 'C15 H30 N3 O3 P Se' _chemical_formula_weight 410.35 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.833(3) _cell_length_b 16.484(3) _cell_length_c 19.729(5) _cell_angle_alpha 90.00 _cell_angle_beta 112.196(19) _cell_angle_gamma 90.00 _cell_volume 3864.2(15) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6150 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 25.11 _exptl_crystal_description palte _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1712 _exptl_absorpt_coefficient_mu 2.043 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.631 _exptl_absorpt_correction_T_max 0.910 _exptl_absorpt_process_details 'Oxford Diffraction, CrysAlis 1.171.30' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KM4-CCD _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26730 _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_sigmaI/netI 0.0515 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 25.11 _reflns_number_total 6846 _reflns_number_gt 4887 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, date)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, date)' _computing_data_reduction 'CrysAlis RED ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material SHELXL-97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0326P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6846 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0551 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0655 _refine_ls_wR_factor_gt 0.0582 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 0.962 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1A Se 0.68165(2) 0.358787(16) 0.318962(15) 0.02536(8) Uani 1 1 d . . . P1A P 0.78181(6) 0.29377(4) 0.41312(4) 0.01892(16) Uani 1 1 d . . . O14A O 0.89740(15) 0.57411(10) 0.58341(10) 0.0280(5) Uani 1 1 d . . . O24A O 1.02138(16) 0.16513(11) 0.25780(10) 0.0290(5) Uani 1 1 d . . . O34A O 0.79874(15) 0.00675(11) 0.56885(10) 0.0304(5) Uani 1 1 d . . . N11A N 0.86232(17) 0.41679(12) 0.51602(11) 0.0185(5) Uani 1 1 d . . . N21A N 0.92401(17) 0.22337(12) 0.35693(11) 0.0193(5) Uani 1 1 d . . . N31A N 0.77478(18) 0.14295(12) 0.47487(11) 0.0213(5) Uani 1 1 d . . . C11A C 0.8052(2) 0.33804(14) 0.50253(14) 0.0192(6) Uani 1 1 d . . . H11A H 0.7315 0.3444 0.5072 0.023 Uiso 1 1 calc R . . H11B H 0.8505 0.2996 0.5409 0.023 Uiso 1 1 calc R . . C12A C 0.7805(2) 0.48319(14) 0.48917(14) 0.0218(6) Uani 1 1 d . . . H12A H 0.7243 0.4796 0.5123 0.026 Uiso 1 1 calc R . . H12B H 0.7402 0.4781 0.4355 0.026 Uiso 1 1 calc R . . C13A C 0.8395(2) 0.56426(16) 0.50690(14) 0.0283(7) Uani 1 1 d . . . H13A H 0.8938 0.5684 0.4823 0.034 Uiso 1 1 calc R . . H13B H 0.7835 0.6083 0.4879 0.034 Uiso 1 1 calc R . . C15A C 0.9789(2) 0.51070(17) 0.61061(15) 0.0317(7) Uani 1 1 d . . . H15A H 1.0191 0.5173 0.6641 0.038 Uiso 1 1 calc R . . H15B H 1.0349 0.5148 0.5874 0.038 Uiso 1 1 calc R . . C16A C 0.9239(2) 0.42806(16) 0.59494(14) 0.0247(6) Uani 1 1 d . . . H16A H 0.9822 0.3855 0.6136 0.030 Uiso 1 1 calc R . . H16B H 0.8713 0.4226 0.6206 0.030 Uiso 1 1 calc R . . C21A C 0.9239(2) 0.26787(16) 0.42132(14) 0.0211(6) Uani 1 1 d . . . H21A H 0.9686 0.3182 0.4272 0.025 Uiso 1 1 calc R . . H21B H 0.9601 0.2342 0.4656 0.025 Uiso 1 1 calc R . . C22A C 0.9421(2) 0.27695(16) 0.30308(14) 0.0232(6) Uani 1 1 d . . . H22A H 1.0160 0.3042 0.3255 0.028 Uiso 1 1 calc R . . H22B H 0.8829 0.3192 0.2875 0.028 Uiso 1 1 calc R . . C23A C 0.9386(2) 0.22832(16) 0.23747(14) 0.0264(7) Uani 1 1 d . . . H23A H 0.8629 0.2041 0.2134 0.032 Uiso 1 1 calc R . . H23B H 0.9521 0.2648 0.2018 0.032 Uiso 1 1 calc R . . C25A C 1.0050(2) 0.11340(16) 0.31108(15) 0.0298(7) Uani 1 1 d . . . H25A H 1.0634 0.0706 0.3255 0.036 Uiso 1 1 calc R . . H25B H 0.9306 0.0866 0.2892 0.036 Uiso 1 1 calc R . . C26A C 1.0107(2) 0.15992(15) 0.37794(14) 0.0229(6) Uani 1 1 d . . . H26A H 0.9987 0.1226 0.4136 0.027 Uiso 1 1 calc R . . H26B H 1.0860 0.1849 0.4014 0.027 Uiso 1 1 calc R . . C31A C 0.7138(2) 0.19622(15) 0.41309(15) 0.0254(6) Uani 1 1 d . . . H31A H 0.6379 0.2066 0.4133 0.030 Uiso 1 1 calc R . . H31B H 0.7039 0.1674 0.3671 0.030 Uiso 1 1 calc R . . C32A C 0.7244(2) 0.14140(16) 0.53036(15) 0.0291(7) Uani 1 1 d . . . H32A H 0.6464 0.1207 0.5083 0.035 Uiso 1 1 calc R . . H32B H 0.7218 0.1971 0.5484 0.035 Uiso 1 1 calc R . . C33A C 0.7930(2) 0.08753(16) 0.59346(16) 0.0305(7) Uani 1 1 d . . . H33A H 0.8701 0.1098 0.6168 0.037 Uiso 1 1 calc R . . H33B H 0.7584 0.0867 0.6306 0.037 Uiso 1 1 calc R . . C35A C 0.8483(2) 0.00841(16) 0.51506(15) 0.0286(7) Uani 1 1 d . . . H35A H 0.8532 -0.0476 0.4984 0.034 Uiso 1 1 calc R . . H35B H 0.9257 0.0303 0.5373 0.034 Uiso 1 1 calc R . . C36A C 0.7810(2) 0.05960(15) 0.45039(15) 0.0249(6) Uani 1 1 d . . . H36A H 0.8170 0.0595 0.4140 0.030 Uiso 1 1 calc R . . H36B H 0.7042 0.0370 0.4268 0.030 Uiso 1 1 calc R . . Se1B Se 0.10133(2) 0.337159(17) 0.117156(15) 0.02627(8) Uani 1 1 d . . . P1B P 0.24922(6) 0.28424(4) 0.19450(4) 0.01824(16) Uani 1 1 d . . . O14B O 0.38564(16) 0.54275(11) 0.38649(11) 0.0349(5) Uani 1 1 d . . . O24B O 0.45832(15) 0.26890(11) -0.00455(10) 0.0269(5) Uani 1 1 d . . . O34B O 0.45508(15) 0.00331(10) 0.33821(10) 0.0284(5) Uani 1 1 d . . . N11B N 0.33399(17) 0.39352(12) 0.30709(11) 0.0180(5) Uani 1 1 d . . . N21B N 0.38802(17) 0.26829(12) 0.11703(11) 0.0174(5) Uani 1 1 d . . . N31B N 0.32883(17) 0.13517(12) 0.25205(11) 0.0182(5) Uani 1 1 d . . . C11B C 0.2830(2) 0.31310(15) 0.29003(13) 0.0189(6) Uani 1 1 d . . . H11C H 0.2133 0.3122 0.3003 0.023 Uiso 1 1 calc R . . H11D H 0.3355 0.2726 0.3223 0.023 Uiso 1 1 calc R . . C12B C 0.2489(2) 0.45768(15) 0.29417(16) 0.0260(7) Uani 1 1 d . . . H12C H 0.2042 0.4478 0.3247 0.031 Uiso 1 1 calc R . . H12D H 0.1970 0.4573 0.2422 0.031 Uiso 1 1 calc R . . C13B C 0.3069(2) 0.53921(17) 0.31325(17) 0.0348(8) Uani 1 1 d . . . H13C H 0.3462 0.5504 0.2797 0.042 Uiso 1 1 calc R . . H13D H 0.2494 0.5820 0.3058 0.042 Uiso 1 1 calc R . . C15B C 0.4671(2) 0.47980(16) 0.39884(16) 0.0289(7) Uani 1 1 d . . . H15C H 0.5210 0.4820 0.4503 0.035 Uiso 1 1 calc R . . H15D H 0.5097 0.4885 0.3668 0.035 Uiso 1 1 calc R . . C16B C 0.4123(2) 0.39770(16) 0.38350(13) 0.0237(6) Uani 1 1 d . . . H14D H 0.4706 0.3552 0.3930 0.028 Uiso 1 1 calc R . . H16C H 0.3712 0.3880 0.4163 0.028 Uiso 1 1 calc R . . C21B C 0.3836(2) 0.30191(16) 0.18454(14) 0.0205(6) Uani 1 1 d . . . H21C H 0.3975 0.3611 0.1856 0.025 Uiso 1 1 calc R . . H21D H 0.4448 0.2775 0.2269 0.025 Uiso 1 1 calc R . . C22B C 0.3405(2) 0.32475(16) 0.05539(13) 0.0231(6) Uani 1 1 d . . . H22C H 0.3835 0.3762 0.0665 0.028 Uiso 1 1 calc R . . H22D H 0.2614 0.3371 0.0479 0.028 Uiso 1 1 calc R . . C23B C 0.3452(2) 0.28799(17) -0.01316(14) 0.0272(7) Uani 1 1 d . . . H23C H 0.2992 0.2380 -0.0254 0.033 Uiso 1 1 calc R . . H23D H 0.3129 0.3266 -0.0543 0.033 Uiso 1 1 calc R . . C25B C 0.5049(2) 0.21498(16) 0.05566(14) 0.0257(7) Uani 1 1 d . . . H25C H 0.5831 0.2015 0.0617 0.031 Uiso 1 1 calc R . . H25D H 0.4609 0.1640 0.0451 0.031 Uiso 1 1 calc R . . C26B C 0.5051(2) 0.25084(16) 0.12599(14) 0.0230(6) Uani 1 1 d . . . H26C H 0.5393 0.2121 0.1668 0.028 Uiso 1 1 calc R . . H26D H 0.5500 0.3014 0.1376 0.028 Uiso 1 1 calc R . . C31B C 0.2333(2) 0.17423(15) 0.19496(14) 0.0221(6) Uani 1 1 d . . . H31C H 0.1634 0.1610 0.2028 0.027 Uiso 1 1 calc R . . H31D H 0.2260 0.1523 0.1466 0.027 Uiso 1 1 calc R . . C32B C 0.2960(2) 0.09404(16) 0.30650(14) 0.0241(6) Uani 1 1 d . . . H32C H 0.2437 0.0491 0.2831 0.029 Uiso 1 1 calc R . . H32D H 0.2569 0.1326 0.3273 0.029 Uiso 1 1 calc R . . C33B C 0.3997(2) 0.06105(17) 0.36688(14) 0.0261(7) Uani 1 1 d . . . H33C H 0.4519 0.1062 0.3902 0.031 Uiso 1 1 calc R . . H33D H 0.3778 0.0349 0.4047 0.031 Uiso 1 1 calc R . . C35B C 0.4859(2) 0.04027(16) 0.28340(14) 0.0261(7) Uani 1 1 d . . . H35C H 0.5220 -0.0008 0.2628 0.031 Uiso 1 1 calc R . . H35D H 0.5420 0.0834 0.3062 0.031 Uiso 1 1 calc R . . C36B C 0.3864(2) 0.07676(15) 0.22179(14) 0.0226(6) Uani 1 1 d . . . H36C H 0.4127 0.1045 0.1866 0.027 Uiso 1 1 calc R . . H36D H 0.3334 0.0333 0.1953 0.027 Uiso 1 1 calc R . . 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 Se1A 0.02716(17) 0.01992(15) 0.02221(15) 0.00117(12) 0.00162(13) 0.00540(12) P1A 0.0187(4) 0.0142(4) 0.0214(4) 0.0011(3) 0.0048(3) 0.0004(3) O14A 0.0342(12) 0.0232(11) 0.0280(11) -0.0080(9) 0.0133(10) -0.0069(9) O24A 0.0333(12) 0.0304(11) 0.0246(11) 0.0017(9) 0.0125(9) 0.0091(9) O34A 0.0337(12) 0.0201(10) 0.0354(12) 0.0065(9) 0.0109(10) -0.0050(9) N11A 0.0217(13) 0.0176(12) 0.0158(11) -0.0001(9) 0.0067(10) -0.0006(10) N21A 0.0209(12) 0.0178(12) 0.0179(12) 0.0019(10) 0.0059(10) 0.0029(9) N31A 0.0244(13) 0.0130(11) 0.0257(12) 0.0032(10) 0.0084(11) 0.0017(10) C11A 0.0193(15) 0.0166(14) 0.0224(14) 0.0042(12) 0.0086(12) 0.0020(11) C12A 0.0272(16) 0.0182(14) 0.0189(14) -0.0009(12) 0.0075(13) 0.0018(12) C13A 0.0389(19) 0.0238(16) 0.0250(16) -0.0012(13) 0.0152(15) -0.0006(13) C15A 0.0319(18) 0.0372(18) 0.0229(16) -0.0078(14) 0.0069(14) -0.0063(14) C16A 0.0245(16) 0.0277(16) 0.0197(15) 0.0012(13) 0.0059(13) 0.0009(12) C21A 0.0205(15) 0.0228(15) 0.0182(14) 0.0023(12) 0.0053(12) 0.0015(12) C22A 0.0270(16) 0.0203(15) 0.0226(15) 0.0020(12) 0.0096(13) -0.0015(12) C23A 0.0319(17) 0.0237(15) 0.0210(15) 0.0042(13) 0.0072(13) 0.0050(13) C25A 0.0327(18) 0.0214(16) 0.0330(17) 0.0019(13) 0.0100(15) 0.0073(13) C26A 0.0193(15) 0.0226(15) 0.0251(15) 0.0037(12) 0.0067(13) 0.0045(12) C31A 0.0230(16) 0.0191(15) 0.0306(16) 0.0015(13) 0.0062(13) -0.0032(12) C32A 0.0318(17) 0.0187(15) 0.0419(18) 0.0008(14) 0.0198(15) -0.0021(13) C33A 0.0351(18) 0.0230(16) 0.0360(18) 0.0026(14) 0.0163(15) -0.0038(14) C35A 0.0236(16) 0.0196(15) 0.0372(18) 0.0006(13) 0.0054(14) 0.0020(12) C36A 0.0236(16) 0.0170(14) 0.0310(16) 0.0000(13) 0.0070(13) -0.0009(12) Se1B 0.02238(16) 0.03391(17) 0.02132(15) 0.00592(13) 0.00688(13) 0.00788(13) P1B 0.0189(4) 0.0196(4) 0.0162(4) -0.0007(3) 0.0066(3) 0.0020(3) O14B 0.0316(12) 0.0270(11) 0.0492(13) -0.0159(10) 0.0187(11) -0.0060(9) O24B 0.0320(12) 0.0294(11) 0.0252(10) 0.0055(9) 0.0174(9) 0.0038(9) O34B 0.0360(12) 0.0206(10) 0.0290(11) 0.0044(9) 0.0128(10) 0.0047(9) N11B 0.0217(13) 0.0162(12) 0.0150(12) -0.0012(9) 0.0055(10) 0.0021(9) N21B 0.0185(12) 0.0213(12) 0.0145(11) 0.0013(9) 0.0087(10) 0.0043(10) N31B 0.0202(12) 0.0168(11) 0.0163(11) -0.0030(10) 0.0053(10) 0.0013(10) C11B 0.0241(16) 0.0162(14) 0.0181(14) -0.0005(11) 0.0097(12) 0.0017(11) C12B 0.0249(16) 0.0220(15) 0.0344(17) -0.0045(13) 0.0150(14) 0.0019(12) C13B 0.0291(18) 0.0240(17) 0.052(2) -0.0034(15) 0.0159(17) 0.0044(13) C15B 0.0257(17) 0.0312(17) 0.0300(17) -0.0060(13) 0.0109(14) -0.0051(13) C16B 0.0275(17) 0.0273(16) 0.0172(14) -0.0008(13) 0.0096(13) 0.0001(13) C21B 0.0177(15) 0.0247(15) 0.0186(14) -0.0019(12) 0.0062(12) -0.0002(12) C22B 0.0266(16) 0.0224(15) 0.0218(15) 0.0080(12) 0.0107(13) 0.0073(12) C23B 0.0269(17) 0.0340(17) 0.0215(15) 0.0068(13) 0.0101(13) 0.0051(13) C25B 0.0289(17) 0.0246(16) 0.0289(16) 0.0037(13) 0.0171(14) 0.0031(13) C26B 0.0207(16) 0.0269(16) 0.0213(15) 0.0025(13) 0.0077(13) 0.0021(12) C31B 0.0215(15) 0.0221(15) 0.0177(14) -0.0053(12) 0.0017(12) -0.0003(12) C32B 0.0241(16) 0.0283(16) 0.0197(15) -0.0060(13) 0.0080(13) -0.0045(13) C33B 0.0289(17) 0.0290(16) 0.0211(15) -0.0002(13) 0.0102(14) -0.0018(13) C35B 0.0287(17) 0.0245(16) 0.0275(16) -0.0013(13) 0.0133(14) 0.0056(13) C36B 0.0304(16) 0.0188(15) 0.0197(14) -0.0026(12) 0.0106(13) 0.0032(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Se1A P1A 2.1088(9) . ? P1A C21A 1.820(3) . ? P1A C11A 1.826(3) . ? P1A C31A 1.830(3) . ? O14A C13A 1.417(3) . ? O14A C15A 1.432(3) . ? O24A C25A 1.430(3) . ? O24A C23A 1.433(3) . ? O34A C35A 1.428(3) . ? O34A C33A 1.429(3) . ? N11A C11A 1.465(3) . ? N11A C16A 1.467(3) . ? N11A C12A 1.470(3) . ? N21A C22A 1.466(3) . ? N21A C21A 1.467(3) . ? N21A C26A 1.468(3) . ? N31A C31A 1.466(3) . ? N31A C32A 1.467(3) . ? N31A C36A 1.468(3) . ? C11A H11A 0.9900 . ? C11A H11B 0.9900 . ? C12A C13A 1.511(4) . ? C12A H12A 0.9900 . ? C12A H12B 0.9900 . ? C13A H13A 0.9900 . ? C13A H13B 0.9900 . ? C15A C16A 1.512(4) . ? C15A H15A 0.9900 . ? C15A H15B 0.9900 . ? C16A H16A 0.9900 . ? C16A H16B 0.9900 . ? C21A H21A 0.9900 . ? C21A H21B 0.9900 . ? C22A C23A 1.509(3) . ? C22A H22A 0.9900 . ? C22A H22B 0.9900 . ? C23A H23A 0.9900 . ? C23A H23B 0.9900 . ? C25A C26A 1.503(4) . ? C25A H25A 0.9900 . ? C25A H25B 0.9900 . ? C26A H26A 0.9900 . ? C26A H26B 0.9900 . ? C31A H31A 0.9900 . ? C31A H31B 0.9900 . ? C32A C33A 1.512(4) . ? C32A H32A 0.9900 . ? C32A H32B 0.9900 . ? C33A H33A 0.9900 . ? C33A H33B 0.9900 . ? C35A C36A 1.501(4) . ? C35A H35A 0.9900 . ? C35A H35B 0.9900 . ? C36A H36A 0.9900 . ? C36A H36B 0.9900 . ? Se1B P1B 2.1220(9) . ? P1B C31B 1.825(3) . ? P1B C11B 1.830(2) . ? P1B C21B 1.832(3) . ? O14B C13B 1.418(3) . ? O14B C15B 1.427(3) . ? O24B C25B 1.422(3) . ? O24B C23B 1.431(3) . ? O34B C35B 1.421(3) . ? O34B C33B 1.426(3) . ? N11B C11B 1.460(3) . ? N11B C16B 1.464(3) . ? N11B C12B 1.472(3) . ? N21B C21B 1.463(3) . ? N21B C22B 1.469(3) . ? N21B C26B 1.474(3) . ? N31B C32B 1.460(3) . ? N31B C31B 1.464(3) . ? N31B C36B 1.471(3) . ? C11B H11C 0.9900 . ? C11B H11D 0.9900 . ? C12B C13B 1.513(4) . ? C12B H12C 0.9900 . ? C12B H12D 0.9900 . ? C13B H13C 0.9900 . ? C13B H13D 0.9900 . ? C15B C16B 1.502(4) . ? C15B H15C 0.9900 . ? C15B H15D 0.9900 . ? C16B H14D 0.9900 . ? C16B H16C 0.9900 . ? C21B H21C 0.9900 . ? C21B H21D 0.9900 . ? C22B C23B 1.504(3) . ? C22B H22C 0.9900 . ? C22B H22D 0.9900 . ? C23B H23C 0.9900 . ? C23B H23D 0.9900 . ? C25B C26B 1.507(3) . ? C25B H25C 0.9900 . ? C25B H25D 0.9900 . ? C26B H26C 0.9900 . ? C26B H26D 0.9900 . ? C31B H31C 0.9900 . ? C31B H31D 0.9900 . ? C32B C33B 1.512(4) . ? C32B H32C 0.9900 . ? C32B H32D 0.9900 . ? C33B H33C 0.9900 . ? C33B H33D 0.9900 . ? C35B C36B 1.516(3) . ? C35B H35C 0.9900 . ? C35B H35D 0.9900 . ? C36B H36C 0.9900 . ? C36B H36D 0.9900 . ? 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 C21A P1A C11A 102.38(12) . . ? C21A P1A C31A 104.82(12) . . ? C11A P1A C31A 104.82(12) . . ? C21A P1A Se1A 117.03(9) . . ? C11A P1A Se1A 118.10(9) . . ? C31A P1A Se1A 108.32(9) . . ? C13A O14A C15A 109.3(2) . . ? C25A O24A C23A 109.87(19) . . ? C35A O34A C33A 109.2(2) . . ? C11A N11A C16A 109.70(19) . . ? C11A N11A C12A 110.72(19) . . ? C16A N11A C12A 108.2(2) . . ? C22A N21A C21A 112.2(2) . . ? C22A N21A C26A 108.9(2) . . ? C21A N21A C26A 111.1(2) . . ? C31A N31A C32A 112.6(2) . . ? C31A N31A C36A 111.4(2) . . ? C32A N31A C36A 108.9(2) . . ? N11A C11A P1A 114.72(17) . . ? N11A C11A H11A 108.6 . . ? P1A C11A H11A 108.6 . . ? N11A C11A H11B 108.6 . . ? P1A C11A H11B 108.6 . . ? H11A C11A H11B 107.6 . . ? N11A C12A C13A 110.3(2) . . ? N11A C12A H12A 109.6 . . ? C13A C12A H12A 109.6 . . ? N11A C12A H12B 109.6 . . ? C13A C12A H12B 109.6 . . ? H12A C12A H12B 108.1 . . ? O14A C13A C12A 111.3(2) . . ? O14A C13A H13A 109.4 . . ? C12A C13A H13A 109.4 . . ? O14A C13A H13B 109.4 . . ? C12A C13A H13B 109.4 . . ? H13A C13A H13B 108.0 . . ? O14A C15A C16A 111.2(2) . . ? O14A C15A H15A 109.4 . . ? C16A C15A H15A 109.4 . . ? O14A C15A H15B 109.4 . . ? C16A C15A H15B 109.4 . . ? H15A C15A H15B 108.0 . . ? N11A C16A C15A 110.7(2) . . ? N11A C16A H16A 109.5 . . ? C15A C16A H16A 109.5 . . ? N11A C16A H16B 109.5 . . ? C15A C16A H16B 109.5 . . ? H16A C16A H16B 108.1 . . ? N21A C21A P1A 111.65(17) . . ? N21A C21A H21A 109.3 . . ? P1A C21A H21A 109.3 . . ? N21A C21A H21B 109.3 . . ? P1A C21A H21B 109.3 . . ? H21A C21A H21B 108.0 . . ? N21A C22A C23A 109.9(2) . . ? N21A C22A H22A 109.7 . . ? C23A C22A H22A 109.7 . . ? N21A C22A H22B 109.7 . . ? C23A C22A H22B 109.7 . . ? H22A C22A H22B 108.2 . . ? O24A C23A C22A 111.6(2) . . ? O24A C23A H23A 109.3 . . ? C22A C23A H23A 109.3 . . ? O24A C23A H23B 109.3 . . ? C22A C23A H23B 109.3 . . ? H23A C23A H23B 108.0 . . ? O24A C25A C26A 111.6(2) . . ? O24A C25A H25A 109.3 . . ? C26A C25A H25A 109.3 . . ? O24A C25A H25B 109.3 . . ? C26A C25A H25B 109.3 . . ? H25A C25A H25B 108.0 . . ? N21A C26A C25A 109.6(2) . . ? N21A C26A H26A 109.8 . . ? C25A C26A H26A 109.8 . . ? N21A C26A H26B 109.8 . . ? C25A C26A H26B 109.8 . . ? H26A C26A H26B 108.2 . . ? N31A C31A P1A 114.92(18) . . ? N31A C31A H31A 108.5 . . ? P1A C31A H31A 108.5 . . ? N31A C31A H31B 108.5 . . ? P1A C31A H31B 108.5 . . ? H31A C31A H31B 107.5 . . ? N31A C32A C33A 109.9(2) . . ? N31A C32A H32A 109.7 . . ? C33A C32A H32A 109.7 . . ? N31A C32A H32B 109.7 . . ? C33A C32A H32B 109.7 . . ? H32A C32A H32B 108.2 . . ? O34A C33A C32A 110.9(2) . . ? O34A C33A H33A 109.5 . . ? C32A C33A H33A 109.5 . . ? O34A C33A H33B 109.5 . . ? C32A C33A H33B 109.5 . . ? H33A C33A H33B 108.1 . . ? O34A C35A C36A 111.6(2) . . ? O34A C35A H35A 109.3 . . ? C36A C35A H35A 109.3 . . ? O34A C35A H35B 109.3 . . ? C36A C35A H35B 109.3 . . ? H35A C35A H35B 108.0 . . ? N31A C36A C35A 109.4(2) . . ? N31A C36A H36A 109.8 . . ? C35A C36A H36A 109.8 . . ? N31A C36A H36B 109.8 . . ? C35A C36A H36B 109.8 . . ? H36A C36A H36B 108.2 . . ? C31B P1B C11B 103.69(12) . . ? C31B P1B C21B 105.66(12) . . ? C11B P1B C21B 101.69(12) . . ? C31B P1B Se1B 109.92(9) . . ? C11B P1B Se1B 115.69(9) . . ? C21B P1B Se1B 118.70(9) . . ? C13B O14B C15B 109.8(2) . . ? C25B O24B C23B 108.92(19) . . ? C35B O34B C33B 109.84(19) . . ? C11B N11B C16B 110.7(2) . . ? C11B N11B C12B 112.0(2) . . ? C16B N11B C12B 108.7(2) . . ? C21B N21B C22B 111.52(19) . . ? C21B N21B C26B 110.67(19) . . ? C22B N21B C26B 107.99(19) . . ? C32B N31B C31B 112.4(2) . . ? C32B N31B C36B 108.86(19) . . ? C31B N31B C36B 112.24(19) . . ? N11B C11B P1B 112.63(17) . . ? N11B C11B H11C 109.1 . . ? P1B C11B H11C 109.1 . . ? N11B C11B H11D 109.1 . . ? P1B C11B H11D 109.1 . . ? H11C C11B H11D 107.8 . . ? N11B C12B C13B 109.4(2) . . ? N11B C12B H12C 109.8 . . ? C13B C12B H12C 109.8 . . ? N11B C12B H12D 109.8 . . ? C13B C12B H12D 109.8 . . ? H12C C12B H12D 108.2 . . ? O14B C13B C12B 112.6(2) . . ? O14B C13B H13C 109.1 . . ? C12B C13B H13C 109.1 . . ? O14B C13B H13D 109.1 . . ? C12B C13B H13D 109.1 . . ? H13C C13B H13D 107.8 . . ? O14B C15B C16B 111.3(2) . . ? O14B C15B H15C 109.4 . . ? C16B C15B H15C 109.4 . . ? O14B C15B H15D 109.4 . . ? C16B C15B H15D 109.4 . . ? H15C C15B H15D 108.0 . . ? N11B C16B C15B 109.7(2) . . ? N11B C16B H14D 109.7 . . ? C15B C16B H14D 109.7 . . ? N11B C16B H16C 109.7 . . ? C15B C16B H16C 109.7 . . ? H14D C16B H16C 108.2 . . ? N21B C21B P1B 113.52(17) . . ? N21B C21B H21C 108.9 . . ? P1B C21B H21C 108.9 . . ? N21B C21B H21D 108.9 . . ? P1B C21B H21D 108.9 . . ? H21C C21B H21D 107.7 . . ? N21B C22B C23B 110.1(2) . . ? N21B C22B H22C 109.6 . . ? C23B C22B H22C 109.6 . . ? N21B C22B H22D 109.6 . . ? C23B C22B H22D 109.6 . . ? H22C C22B H22D 108.2 . . ? O24B C23B C22B 111.5(2) . . ? O24B C23B H23C 109.3 . . ? C22B C23B H23C 109.3 . . ? O24B C23B H23D 109.3 . . ? C22B C23B H23D 109.3 . . ? H23C C23B H23D 108.0 . . ? O24B C25B C26B 112.2(2) . . ? O24B C25B H25C 109.2 . . ? C26B C25B H25C 109.2 . . ? O24B C25B H25D 109.2 . . ? C26B C25B H25D 109.2 . . ? H25C C25B H25D 107.9 . . ? N21B C26B C25B 108.6(2) . . ? N21B C26B H26C 110.0 . . ? C25B C26B H26C 110.0 . . ? N21B C26B H26D 110.0 . . ? C25B C26B H26D 110.0 . . ? H26C C26B H26D 108.3 . . ? N31B C31B P1B 112.22(17) . . ? N31B C31B H31C 109.2 . . ? P1B C31B H31C 109.2 . . ? N31B C31B H31D 109.2 . . ? P1B C31B H31D 109.2 . . ? H31C C31B H31D 107.9 . . ? N31B C32B C33B 109.5(2) . . ? N31B C32B H32C 109.8 . . ? C33B C32B H32C 109.8 . . ? N31B C32B H32D 109.8 . . ? C33B C32B H32D 109.8 . . ? H32C C32B H32D 108.2 . . ? O34B C33B C32B 110.4(2) . . ? O34B C33B H33C 109.6 . . ? C32B C33B H33C 109.6 . . ? O34B C33B H33D 109.6 . . ? C32B C33B H33D 109.6 . . ? H33C C33B H33D 108.1 . . ? O34B C35B C36B 112.8(2) . . ? O34B C35B H35C 109.0 . . ? C36B C35B H35C 109.0 . . ? O34B C35B H35D 109.0 . . ? C36B C35B H35D 109.0 . . ? H35C C35B H35D 107.8 . . ? N31B C36B C35B 109.6(2) . . ? N31B C36B H36C 109.8 . . ? C35B C36B H36C 109.8 . . ? N31B C36B H36D 109.8 . . ? C35B C36B H36D 109.8 . . ? H36C C36B H36D 108.2 . . ? 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 C16A N11A C11A P1A -152.81(18) . . . . ? C12A N11A C11A P1A 87.8(2) . . . . ? C21A P1A C11A N11A 69.3(2) . . . . ? C31A P1A C11A N11A 178.51(18) . . . . ? Se1A P1A C11A N11A -60.8(2) . . . . ? C11A N11A C12A C13A 177.0(2) . . . . ? C16A N11A C12A C13A 56.7(3) . . . . ? C15A O14A C13A C12A 59.5(3) . . . . ? N11A C12A C13A O14A -59.8(3) . . . . ? C13A O14A C15A C16A -58.7(3) . . . . ? C11A N11A C16A C15A -177.2(2) . . . . ? C12A N11A C16A C15A -56.3(3) . . . . ? O14A C15A C16A N11A 58.3(3) . . . . ? C22A N21A C21A P1A 95.5(2) . . . . ? C26A N21A C21A P1A -142.36(18) . . . . ? C11A P1A C21A N21A 174.36(17) . . . . ? C31A P1A C21A N21A 65.2(2) . . . . ? Se1A P1A C21A N21A -54.86(19) . . . . ? C21A N21A C22A C23A -178.7(2) . . . . ? C26A N21A C22A C23A 57.9(3) . . . . ? C25A O24A C23A C22A 57.2(3) . . . . ? N21A C22A C23A O24A -58.1(3) . . . . ? C23A O24A C25A C26A -57.9(3) . . . . ? C22A N21A C26A C25A -58.3(3) . . . . ? C21A N21A C26A C25A 177.6(2) . . . . ? O24A C25A C26A N21A 59.1(3) . . . . ? C32A N31A C31A P1A 103.7(2) . . . . ? C36A N31A C31A P1A -133.7(2) . . . . ? C21A P1A C31A N31A 53.2(2) . . . . ? C11A P1A C31A N31A -54.2(2) . . . . ? Se1A P1A C31A N31A 178.88(16) . . . . ? C31A N31A C32A C33A -178.3(2) . . . . ? C36A N31A C32A C33A 57.7(3) . . . . ? C35A O34A C33A C32A 58.9(3) . . . . ? N31A C32A C33A O34A -59.0(3) . . . . ? C33A O34A C35A C36A -59.7(3) . . . . ? C31A N31A C36A C35A 177.6(2) . . . . ? C32A N31A C36A C35A -57.7(3) . . . . ? O34A C35A C36A N31A 59.7(3) . . . . ? C16B N11B C11B P1B -149.03(18) . . . . ? C12B N11B C11B P1B 89.5(2) . . . . ? C31B P1B C11B N11B 161.61(18) . . . . ? C21B P1B C11B N11B 52.1(2) . . . . ? Se1B P1B C11B N11B -77.97(18) . . . . ? C11B N11B C12B C13B 179.7(2) . . . . ? C16B N11B C12B C13B 57.0(3) . . . . ? C15B O14B C13B C12B 57.0(3) . . . . ? N11B C12B C13B O14B -57.3(3) . . . . ? C13B O14B C15B C16B -58.0(3) . . . . ? C11B N11B C16B C15B 177.7(2) . . . . ? C12B N11B C16B C15B -58.9(3) . . . . ? O14B C15B C16B N11B 60.0(3) . . . . ? C22B N21B C21B P1B 85.3(2) . . . . ? C26B N21B C21B P1B -154.49(17) . . . . ? C31B P1B C21B N21B 60.3(2) . . . . ? C11B P1B C21B N21B 168.35(18) . . . . ? Se1B P1B C21B N21B -63.5(2) . . . . ? C21B N21B C22B C23B -179.4(2) . . . . ? C26B N21B C22B C23B 58.8(3) . . . . ? C25B O24B C23B C22B 57.7(3) . . . . ? N21B C22B C23B O24B -59.1(3) . . . . ? C23B O24B C25B C26B -59.0(3) . . . . ? C21B N21B C26B C25B 179.0(2) . . . . ? C22B N21B C26B C25B -58.7(3) . . . . ? O24B C25B C26B N21B 60.6(3) . . . . ? C32B N31B C31B P1B 116.7(2) . . . . ? C36B N31B C31B P1B -120.22(19) . . . . ? C11B P1B C31B N31B -50.5(2) . . . . ? C21B P1B C31B N31B 56.0(2) . . . . ? Se1B P1B C31B N31B -174.78(15) . . . . ? C31B N31B C32B C33B -175.4(2) . . . . ? C36B N31B C32B C33B 59.6(3) . . . . ? C35B O34B C33B C32B 58.8(3) . . . . ? N31B C32B C33B O34B -61.3(3) . . . . ? C33B O34B C35B C36B -56.9(3) . . . . ? C32B N31B C36B C35B -56.5(3) . . . . ? C31B N31B C36B C35B 178.5(2) . . . . ? O34B C35B C36B N31B 56.1(3) . . . . ? 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 C12A H12B Se1A 0.99 2.90 3.725(3) 141 . C22A H22B Se1A 0.99 2.95 3.726(3) 136 . C22B H22D Se1B 0.99 2.86 3.711(3) 144 . C21A H21A O14A 0.99 2.53 3.495(3) 163 3_766 C25A H25A O34A 0.99 2.51 3.372(3) 145 3_756 C31B H31C O24A 0.99 2.45 3.393(3) 159 1_455 C36B H36D Se1A 0.99 2.89 3.713(3) 141 2_645 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.373 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.067