# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_exp_782 _database_code_depnum_ccdc_archive 'CCDC 878241' #TrackingRef 'exp_782.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H20 N P S' _chemical_formula_sum 'C20 H20 N P S' _chemical_formula_weight 337.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 41 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x, z+1/4' '-x, -y, z+1/2' 'y, -x, z+3/4' _cell_length_a 11.8572(2) _cell_length_b 11.8572(2) _cell_length_c 12.3816(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1740.77(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.73 _cell_measurement_theta_max 70.80 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 2.489 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.58 _exptl_absorpt_correction_T_max 0.74 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'supernova Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3803 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0484 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.73 _diffrn_reflns_theta_max 70.80 _reflns_number_total 2402 _reflns_number_gt 2316 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP III & Olex 2.1' _computing_publication_material WinGX _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^ > 2\s(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^)+(0.0419P)^2^+0.0426P] 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 0.01(2) _refine_ls_number_reflns 2402 _refine_ls_number_parameters 210 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0336 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0827 _refine_ls_wR_factor_gt 0.0811 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 1.04375(5) 0.54488(6) 0.14483(5) 0.03221(17) Uani 1 1 d . . . P1 P 0.95714(5) 0.50044(5) 0.01772(5) 0.02284(15) Uani 1 1 d . . . N1 N 1.02095(16) 0.53823(17) -0.09620(18) 0.0240(4) Uani 1 1 d . . . H1 H 0.9848 0.5284 -0.1557 0.029 Uiso 1 1 calc R . . C1 C 1.13206(19) 0.5861(2) -0.1025(2) 0.0233(5) Uani 1 1 d . . . C2 C 1.2237(2) 0.5144(2) -0.12177(18) 0.0265(5) Uani 1 1 d . . . C3 C 1.3303(2) 0.5633(3) -0.1346(2) 0.0325(6) Uani 1 1 d . . . H15 H 1.3925 0.5174 -0.1472 0.039 Uiso 1 1 calc R . . C4 C 1.3447(2) 0.6791(3) -0.1288(2) 0.0348(6) Uani 1 1 d . . . H19 H 1.4157 0.7104 -0.1390 0.042 Uiso 1 1 calc R . . C5 C 1.2533(2) 0.7477(2) -0.1078(2) 0.0343(6) Uani 1 1 d . . . H5 H 1.2639 0.8253 -0.1028 0.041 Uiso 1 1 calc R . . C6 C 1.1455(2) 0.7033(2) -0.0940(2) 0.0297(5) Uani 1 1 d . . . C7 C 1.2076(2) 0.3896(2) -0.1312(2) 0.0322(6) Uani 1 1 d . . . H14A H 1.1605 0.3734 -0.1924 0.048 Uiso 1 1 calc R . . H14B H 1.1723 0.3615 -0.0668 0.048 Uiso 1 1 calc R . . H14C H 1.2795 0.3538 -0.1406 0.048 Uiso 1 1 calc R . . C8 C 1.0473(3) 0.7808(2) -0.0727(3) 0.0430(7) Uani 1 1 d . . . H21A H 1.0218 0.7710 0.0003 0.065 Uiso 1 1 calc R . . H21B H 0.9870 0.7633 -0.1217 0.065 Uiso 1 1 calc R . . H21C H 1.0705 0.8576 -0.0832 0.065 Uiso 1 1 calc R . . C9 C 0.81737(19) 0.56176(19) 0.0115(2) 0.0241(5) Uani 1 1 d . . . C10 C 0.7451(2) 0.5429(2) 0.0984(2) 0.0285(5) Uani 1 1 d . . . H8 H 0.7686 0.4984 0.1561 0.034 Uiso 1 1 calc R . . C11 C 0.6378(2) 0.5905(2) 0.0990(2) 0.0322(6) Uani 1 1 d . . . H6 H 0.5899 0.5783 0.1572 0.039 Uiso 1 1 calc R . . C12 C 0.6025(2) 0.6560(2) 0.0128(2) 0.0330(6) Uani 1 1 d . . . H9 H 0.5312 0.6887 0.0137 0.040 Uiso 1 1 calc R . . C13 C 0.6732(2) 0.6730(2) -0.0750(2) 0.0311(6) Uani 1 1 d . . . H13 H 0.6487 0.7158 -0.1334 0.037 Uiso 1 1 calc R . . C14 C 0.7810(2) 0.6259(2) -0.0756(2) 0.0278(5) Uani 1 1 d . . . H3 H 0.8285 0.6375 -0.1343 0.033 Uiso 1 1 calc R . . C15 C 0.92739(19) 0.3500(2) 0.0103(2) 0.0262(5) Uani 1 1 d . . . C16 C 0.9346(2) 0.2832(2) 0.1026(3) 0.0350(6) Uani 1 1 d . . . H4 H 0.9589 0.3139 0.1676 0.042 Uiso 1 1 calc R . . C17 C 0.9048(3) 0.1692(3) 0.0962(3) 0.0447(8) Uani 1 1 d . . . H17 H 0.9097 0.1240 0.1574 0.054 Uiso 1 1 calc R . . C18 C 0.8687(2) 0.1237(2) 0.0007(3) 0.0435(8) Uani 1 1 d . . . H20 H 0.8494 0.0478 -0.0026 0.052 Uiso 1 1 calc R . . C19 C 0.8607(2) 0.1900(2) -0.0910(3) 0.0396(7) Uani 1 1 d . . . H11 H 0.8359 0.1588 -0.1557 0.048 Uiso 1 1 calc R . . C20 C 0.8900(2) 0.3031(2) -0.0860(2) 0.0335(6) Uani 1 1 d . . . H10 H 0.8845 0.3478 -0.1475 0.040 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 0.0275(3) 0.0493(4) 0.0198(3) -0.0005(3) -0.0026(3) -0.0074(3) P1 0.0211(3) 0.0272(3) 0.0202(3) 0.0016(3) -0.0002(3) -0.0027(2) N1 0.0214(9) 0.0316(11) 0.0192(9) -0.0010(9) -0.0001(8) -0.0054(8) C1 0.0220(11) 0.0297(12) 0.0183(9) 0.0032(10) 0.0003(9) -0.0048(9) C2 0.0282(12) 0.0340(13) 0.0173(11) -0.0001(10) -0.0010(10) -0.0013(10) C3 0.0229(12) 0.0479(16) 0.0267(13) 0.0007(12) -0.0007(10) 0.0015(11) C4 0.0290(13) 0.0517(17) 0.0237(12) 0.0051(12) -0.0030(11) -0.0130(13) C5 0.0422(15) 0.0312(13) 0.0296(11) 0.0035(12) -0.0006(13) -0.0131(11) C6 0.0346(13) 0.0298(13) 0.0248(12) 0.0025(11) 0.0009(11) -0.0039(11) C7 0.0341(14) 0.0324(13) 0.0300(14) -0.0001(11) -0.0011(11) 0.0057(11) C8 0.0486(17) 0.0267(14) 0.0537(19) -0.0044(13) 0.0067(16) -0.0007(12) C9 0.0225(11) 0.0247(11) 0.0250(11) -0.0036(11) 0.0009(11) -0.0035(9) C10 0.0307(13) 0.0301(13) 0.0248(12) 0.0002(11) -0.0003(11) -0.0014(11) C11 0.0258(13) 0.0376(14) 0.0332(14) -0.0066(12) 0.0032(11) 0.0003(11) C12 0.0264(12) 0.0379(13) 0.0347(13) -0.0102(13) -0.0001(12) 0.0045(10) C13 0.0356(14) 0.0305(13) 0.0272(13) 0.0006(11) -0.0055(11) 0.0061(11) C14 0.0270(12) 0.0302(13) 0.0263(13) 0.0014(10) 0.0008(11) -0.0004(10) C15 0.0189(10) 0.0283(11) 0.0313(12) 0.0050(12) 0.0013(11) 0.0011(9) C16 0.0280(13) 0.0385(15) 0.0384(15) 0.0082(13) -0.0023(12) 0.0009(12) C17 0.0353(16) 0.0372(15) 0.061(2) 0.0220(16) 0.0066(15) 0.0026(13) C18 0.0341(14) 0.0267(13) 0.070(2) 0.0036(15) 0.0119(16) -0.0020(10) C19 0.0349(14) 0.0363(14) 0.0475(17) -0.0059(14) 0.0084(14) -0.0062(12) C20 0.0339(14) 0.0307(13) 0.0360(15) 0.0029(12) 0.0012(12) -0.0054(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.9516(8) . ? P1 N1 1.662(2) . ? P1 C9 1.811(2) . ? P1 C15 1.821(2) . ? N1 C1 1.437(3) . ? N1 H1 0.8600 . ? C1 C2 1.400(3) . ? C1 C6 1.403(3) . ? C2 C3 1.400(4) . ? C2 C7 1.497(4) . ? C3 C4 1.385(4) . ? C3 H15 0.9300 . ? C4 C5 1.380(4) . ? C4 H19 0.9300 . ? C5 C6 1.393(4) . ? C5 H5 0.9300 . ? C6 C8 1.507(4) . ? C7 H14A 0.9600 . ? C7 H14B 0.9600 . ? C7 H14C 0.9600 . ? C8 H21A 0.9600 . ? C8 H21B 0.9600 . ? C8 H21C 0.9600 . ? C9 C14 1.388(4) . ? C9 C10 1.394(4) . ? C10 C11 1.392(4) . ? C10 H8 0.9300 . ? C11 C12 1.385(4) . ? C11 H6 0.9300 . ? C12 C13 1.387(4) . ? C12 H9 0.9300 . ? C13 C14 1.395(4) . ? C13 H13 0.9300 . ? C14 H3 0.9300 . ? C15 C20 1.388(4) . ? C15 C16 1.393(4) . ? C16 C17 1.398(4) . ? C16 H4 0.9300 . ? C17 C18 1.368(5) . ? C17 H17 0.9300 . ? C18 C19 1.385(5) . ? C18 H20 0.9300 . ? C19 C20 1.387(4) . ? C19 H11 0.9300 . ? C20 H10 0.9300 . ? 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 N1 P1 C9 105.80(11) . . ? N1 P1 C15 108.02(12) . . ? C9 P1 C15 102.35(10) . . ? N1 P1 S1 111.84(8) . . ? C9 P1 S1 114.03(9) . . ? C15 P1 S1 114.03(10) . . ? C1 N1 P1 124.76(18) . . ? C1 N1 H1 117.6 . . ? P1 N1 H1 117.6 . . ? C2 C1 C6 121.7(2) . . ? C2 C1 N1 118.8(2) . . ? C6 C1 N1 119.4(2) . . ? C3 C2 C1 118.0(2) . . ? C3 C2 C7 121.1(2) . . ? C1 C2 C7 121.0(2) . . ? C4 C3 C2 121.0(3) . . ? C4 C3 H15 119.5 . . ? C2 C3 H15 119.5 . . ? C5 C4 C3 119.9(2) . . ? C5 C4 H19 120.1 . . ? C3 C4 H19 120.1 . . ? C4 C5 C6 121.3(2) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C5 C6 C1 118.0(2) . . ? C5 C6 C8 120.0(2) . . ? C1 C6 C8 122.0(2) . . ? C2 C7 H14A 109.5 . . ? C2 C7 H14B 109.5 . . ? H14A C7 H14B 109.5 . . ? C2 C7 H14C 109.5 . . ? H14A C7 H14C 109.5 . . ? H14B C7 H14C 109.5 . . ? C6 C8 H21A 109.5 . . ? C6 C8 H21B 109.5 . . ? H21A C8 H21B 109.5 . . ? C6 C8 H21C 109.5 . . ? H21A C8 H21C 109.5 . . ? H21B C8 H21C 109.5 . . ? C14 C9 C10 119.8(2) . . ? C14 C9 P1 122.49(19) . . ? C10 C9 P1 117.7(2) . . ? C11 C10 C9 120.0(3) . . ? C11 C10 H8 120.0 . . ? C9 C10 H8 120.0 . . ? C12 C11 C10 120.0(3) . . ? C12 C11 H6 120.0 . . ? C10 C11 H6 120.0 . . ? C11 C12 C13 120.2(2) . . ? C11 C12 H9 119.9 . . ? C13 C12 H9 119.9 . . ? C12 C13 C14 119.9(2) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C9 C14 C13 120.0(2) . . ? C9 C14 H3 120.0 . . ? C13 C14 H3 120.0 . . ? C20 C15 C16 119.7(2) . . ? C20 C15 P1 119.9(2) . . ? C16 C15 P1 120.3(2) . . ? C15 C16 C17 119.2(3) . . ? C15 C16 H4 120.4 . . ? C17 C16 H4 120.4 . . ? C18 C17 C16 120.6(3) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 120.4(3) . . ? C17 C18 H20 119.8 . . ? C19 C18 H20 119.8 . . ? C18 C19 C20 119.6(3) . . ? C18 C19 H11 120.2 . . ? C20 C19 H11 120.2 . . ? C19 C20 C15 120.4(3) . . ? C19 C20 H10 119.8 . . ? C15 C20 H10 119.8 . . ? 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 C9 P1 N1 C1 131.4(2) . . . . ? C15 P1 N1 C1 -119.6(2) . . . . ? S1 P1 N1 C1 6.7(2) . . . . ? P1 N1 C1 C2 94.8(3) . . . . ? P1 N1 C1 C6 -88.0(3) . . . . ? C6 C1 C2 C3 -1.3(4) . . . . ? N1 C1 C2 C3 176.0(2) . . . . ? C6 C1 C2 C7 -179.7(2) . . . . ? N1 C1 C2 C7 -2.5(4) . . . . ? C1 C2 C3 C4 -0.2(4) . . . . ? C7 C2 C3 C4 178.2(2) . . . . ? C2 C3 C4 C5 1.4(4) . . . . ? C3 C4 C5 C6 -1.1(4) . . . . ? C4 C5 C6 C1 -0.4(4) . . . . ? C4 C5 C6 C8 -179.1(3) . . . . ? C2 C1 C6 C5 1.5(4) . . . . ? N1 C1 C6 C5 -175.7(2) . . . . ? C2 C1 C6 C8 -179.7(3) . . . . ? N1 C1 C6 C8 3.1(4) . . . . ? N1 P1 C9 C14 0.0(2) . . . . ? C15 P1 C9 C14 -113.0(2) . . . . ? S1 P1 C9 C14 123.3(2) . . . . ? N1 P1 C9 C10 -179.93(18) . . . . ? C15 P1 C9 C10 67.0(2) . . . . ? S1 P1 C9 C10 -56.6(2) . . . . ? C14 C9 C10 C11 -1.6(4) . . . . ? P1 C9 C10 C11 178.3(2) . . . . ? C9 C10 C11 C12 0.5(4) . . . . ? C10 C11 C12 C13 0.9(4) . . . . ? C11 C12 C13 C14 -1.3(4) . . . . ? C10 C9 C14 C13 1.2(4) . . . . ? P1 C9 C14 C13 -178.7(2) . . . . ? C12 C13 C14 C9 0.2(4) . . . . ? N1 P1 C15 C20 -40.3(2) . . . . ? C9 P1 C15 C20 71.1(2) . . . . ? S1 P1 C15 C20 -165.27(18) . . . . ? N1 P1 C15 C16 144.1(2) . . . . ? C9 P1 C15 C16 -104.5(2) . . . . ? S1 P1 C15 C16 19.1(2) . . . . ? C20 C15 C16 C17 0.6(4) . . . . ? P1 C15 C16 C17 176.2(2) . . . . ? C15 C16 C17 C18 -0.2(4) . . . . ? C16 C17 C18 C19 -0.2(5) . . . . ? C17 C18 C19 C20 0.2(4) . . . . ? C18 C19 C20 C15 0.2(4) . . . . ? C16 C15 C20 C19 -0.6(4) . . . . ? P1 C15 C20 C19 -176.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 70.80 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.155 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.054 data_exp_308 _database_code_depnum_ccdc_archive 'CCDC 878242' #TrackingRef 'exp_308.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H20 N O P' _chemical_formula_sum 'C20 H20 N O P' _chemical_formula_weight 321.34 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.068(5) _cell_length_b 19.055(5) _cell_length_c 20.228(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.000(5) _cell_angle_gamma 90.000(5) _cell_volume 3495(2) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.47 _cell_measurement_theta_max 25.81 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 0.161 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'supernova Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8782 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 25.81 _reflns_number_total 5909 _reflns_number_gt 5677 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP III & Olex 2.1' _computing_publication_material WinGX _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^ > 2\s(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^)+(0.0590P)^2^+0.8279P] 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 -1.73(8) _refine_ls_number_reflns 5909 _refine_ls_number_parameters 419 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.1043 _refine_ls_wR_factor_gt 0.1023 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.020 _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 P2 P 0.73975(6) 0.03829(3) 0.59683(3) 0.02466(13) Uani 1 1 d . . . P1 P 0.82535(6) 0.06156(3) 0.33849(3) 0.02443(13) Uani 1 1 d . . . O2 O 0.67995(19) 0.00419(8) 0.65754(7) 0.0307(3) Uani 1 1 d . . . O1 O 0.80025(19) 0.05275(9) 0.41082(7) 0.0321(4) Uani 1 1 d . . . N1 N 0.7751(2) -0.00710(10) 0.29458(9) 0.0282(4) Uani 1 1 d . . . H1 H 0.7510 -0.0003 0.2540 0.034 Uiso 1 1 calc R . . C9 C 1.0179(3) 0.08007(11) 0.32296(11) 0.0285(5) Uani 1 1 d . . . N2 N 0.7151(2) -0.01060(10) 0.53055(9) 0.0274(4) Uani 1 1 d . . . H2 H 0.7017 0.0085 0.4925 0.033 Uiso 1 1 calc R . . C15 C 0.7255(2) 0.13471(11) 0.30487(11) 0.0281(5) Uani 1 1 d . . . C38 C 0.5145(3) 0.24989(14) 0.56248(15) 0.0455(7) Uani 1 1 d . . . H38 H 0.4677 0.2929 0.5570 0.055 Uiso 1 1 calc R . . C29 C 0.9335(3) 0.05841(12) 0.60664(11) 0.0294(5) Uani 1 1 d . . . C35 C 0.6544(3) 0.12161(12) 0.57868(11) 0.0283(5) Uani 1 1 d . . . C10 C 1.1183(3) 0.07313(13) 0.37476(12) 0.0358(5) Uani 1 1 d . . . H10 H 1.0858 0.0595 0.4164 0.043 Uiso 1 1 calc R . . C13 C 1.2168(3) 0.11354(15) 0.25091(14) 0.0444(6) Uani 1 1 d . . . H13 H 1.2505 0.1269 0.2093 0.053 Uiso 1 1 calc R . . C2 C 0.6428(3) -0.09907(13) 0.35466(11) 0.0331(5) Uani 1 1 d . . . C20 C 0.6922(3) 0.14228(13) 0.23725(12) 0.0339(5) Uani 1 1 d . . . H20 H 0.7221 0.1082 0.2072 0.041 Uiso 1 1 calc R . . C5 C 0.8672(4) -0.19447(15) 0.32634(13) 0.0454(7) Uani 1 1 d . . . H5 H 0.9402 -0.2269 0.3160 0.054 Uiso 1 1 calc R . . C21 C 0.7162(3) -0.08589(12) 0.53724(11) 0.0321(5) Uani 1 1 d . . . C8 C 0.5175(3) -0.04949(15) 0.36801(13) 0.0405(6) Uani 1 1 d . . . H8A H 0.4330 -0.0756 0.3826 0.061 Uiso 1 1 calc R . . H8B H 0.4935 -0.0245 0.3282 0.061 Uiso 1 1 calc R . . H8C H 0.5460 -0.0167 0.4017 0.061 Uiso 1 1 calc R . . C36 C 0.5724(3) 0.13487(13) 0.52226(13) 0.0357(5) Uani 1 1 d . . . H36 H 0.5639 0.1006 0.4897 0.043 Uiso 1 1 calc R . . C40 C 0.6666(3) 0.17351(13) 0.62721(14) 0.0414(6) Uani 1 1 d . . . H40 H 0.7227 0.1652 0.6649 0.050 Uiso 1 1 calc R . . C17 C 0.6011(3) 0.24425(14) 0.32643(14) 0.0417(6) Uani 1 1 d . . . H17 H 0.5699 0.2783 0.3562 0.050 Uiso 1 1 calc R . . C4 C 0.7452(4) -0.21569(13) 0.36180(13) 0.0475(7) Uani 1 1 d . . . H4 H 0.7377 -0.2619 0.3761 0.057 Uiso 1 1 calc R . . C1 C 0.7689(3) -0.07806(11) 0.31982(10) 0.0291(5) Uani 1 1 d . . . C33 C 1.1575(3) 0.10576(14) 0.56122(13) 0.0406(6) Uani 1 1 d . . . H33 H 1.2067 0.1284 0.5270 0.049 Uiso 1 1 calc R . . C39 C 0.5958(4) 0.23713(14) 0.61941(15) 0.0505(7) Uani 1 1 d . . . H39 H 0.6025 0.2713 0.6521 0.061 Uiso 1 1 calc R . . C19 C 0.6151(3) 0.20054(15) 0.21553(12) 0.0420(6) Uani 1 1 d . . . H19 H 0.5936 0.2054 0.1708 0.050 Uiso 1 1 calc R . . C18 C 0.5698(3) 0.25133(14) 0.25926(15) 0.0443(6) Uani 1 1 d . . . H18 H 0.5183 0.2904 0.2441 0.053 Uiso 1 1 calc R . . C32 C 1.2341(3) 0.08495(15) 0.61691(14) 0.0438(6) Uani 1 1 d . . . H32 H 1.3347 0.0938 0.6203 0.053 Uiso 1 1 calc R . . C16 C 0.6783(3) 0.18675(12) 0.34851(12) 0.0339(5) Uani 1 1 d . . . H16 H 0.6994 0.1825 0.3933 0.041 Uiso 1 1 calc R . . C12 C 1.3154(3) 0.10678(15) 0.30252(16) 0.0465(7) Uani 1 1 d . . . H12 H 1.4151 0.1158 0.2958 0.056 Uiso 1 1 calc R . . C26 C 0.8447(3) -0.12381(13) 0.52377(12) 0.0382(6) Uani 1 1 d . . . C30 C 1.0099(3) 0.03774(15) 0.66286(13) 0.0397(6) Uani 1 1 d . . . H30 H 0.9609 0.0152 0.6972 0.048 Uiso 1 1 calc R . . C34 C 1.0085(3) 0.09304(13) 0.55624(12) 0.0342(5) Uani 1 1 d . . . H34 H 0.9575 0.1077 0.5188 0.041 Uiso 1 1 calc R . . C7 C 1.0213(3) -0.10178(16) 0.27038(14) 0.0448(6) Uani 1 1 d . . . H7A H 1.0765 -0.0708 0.2985 0.067 Uiso 1 1 calc R . . H7B H 0.9951 -0.0777 0.2304 0.067 Uiso 1 1 calc R . . H7C H 1.0802 -0.1421 0.2598 0.067 Uiso 1 1 calc R . . C3 C 0.6341(3) -0.16857(14) 0.37617(12) 0.0414(6) Uani 1 1 d . . . H3 H 0.5527 -0.1833 0.4004 0.050 Uiso 1 1 calc R . . C25 C 0.8420(4) -0.19666(15) 0.53257(13) 0.0526(8) Uani 1 1 d . . . H25 H 0.9265 -0.2228 0.5240 0.063 Uiso 1 1 calc R . . C11 C 1.2659(3) 0.08652(14) 0.36418(15) 0.0446(6) Uani 1 1 d . . . H11 H 1.3325 0.0819 0.3988 0.054 Uiso 1 1 calc R . . C22 C 0.5855(3) -0.11902(14) 0.55608(12) 0.0413(6) Uani 1 1 d . . . C37 C 0.5026(3) 0.19937(15) 0.51413(14) 0.0423(6) Uani 1 1 d . . . H37 H 0.4481 0.2083 0.4761 0.051 Uiso 1 1 calc R . . C31 C 1.1613(3) 0.05116(16) 0.66724(14) 0.0468(6) Uani 1 1 d . . . H31 H 1.2132 0.0370 0.7046 0.056 Uiso 1 1 calc R . . C24 C 0.7168(5) -0.23004(15) 0.55366(15) 0.0627(10) Uani 1 1 d . . . H24 H 0.7174 -0.2783 0.5605 0.075 Uiso 1 1 calc R . . C6 C 0.8826(3) -0.12504(14) 0.30578(12) 0.0364(5) Uani 1 1 d . . . C27 C 0.9828(3) -0.08891(16) 0.49903(15) 0.0477(7) Uani 1 1 d . . . H27A H 0.9621 -0.0648 0.4584 0.072 Uiso 1 1 calc R . . H27B H 1.0574 -0.1238 0.4914 0.072 Uiso 1 1 calc R . . H27C H 1.0173 -0.0559 0.5314 0.072 Uiso 1 1 calc R . . C14 C 1.0687(3) 0.10059(14) 0.26057(13) 0.0371(6) Uani 1 1 d . . . H14 H 1.0027 0.1055 0.2257 0.045 Uiso 1 1 calc R . . C28 C 0.4451(3) -0.07947(18) 0.56578(15) 0.0524(8) Uani 1 1 d . . . H28A H 0.4495 -0.0539 0.6066 0.079 Uiso 1 1 calc R . . H28B H 0.3640 -0.1118 0.5671 0.079 Uiso 1 1 calc R . . H28C H 0.4314 -0.0472 0.5298 0.079 Uiso 1 1 calc R . . C23 C 0.5903(5) -0.19214(17) 0.56474(14) 0.0579(9) Uani 1 1 d . . . H23 H 0.5056 -0.2155 0.5784 0.069 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 P2 0.0285(3) 0.0275(2) 0.0180(2) 0.0012(2) 0.0006(2) -0.0004(2) P1 0.0263(3) 0.0292(3) 0.0178(2) 0.0008(2) 0.0006(2) -0.0026(2) O2 0.0387(9) 0.0337(8) 0.0196(7) 0.0014(6) 0.0017(7) -0.0042(7) O1 0.0382(9) 0.0379(8) 0.0201(7) 0.0005(6) 0.0012(7) -0.0031(7) N1 0.0350(11) 0.0302(9) 0.0192(8) 0.0029(7) -0.0034(8) -0.0032(8) C9 0.0298(11) 0.0278(10) 0.0280(11) -0.0012(9) -0.0013(9) -0.0014(9) N2 0.0354(11) 0.0300(9) 0.0169(8) 0.0032(7) -0.0001(8) 0.0004(8) C15 0.0256(11) 0.0339(11) 0.0247(10) 0.0013(9) -0.0007(9) -0.0027(9) C38 0.0514(16) 0.0337(12) 0.0515(17) 0.0089(12) 0.0125(15) 0.0123(12) C29 0.0307(11) 0.0310(10) 0.0265(10) -0.0037(9) -0.0016(9) 0.0017(9) C35 0.0289(11) 0.0303(10) 0.0256(10) 0.0026(9) 0.0044(9) 0.0019(9) C10 0.0363(13) 0.0397(13) 0.0315(12) -0.0037(10) -0.0035(11) 0.0018(10) C13 0.0378(15) 0.0496(15) 0.0458(15) 0.0038(12) 0.0111(12) -0.0018(12) C2 0.0390(13) 0.0380(12) 0.0224(10) -0.0009(9) -0.0042(10) -0.0074(10) C20 0.0383(13) 0.0396(12) 0.0238(11) -0.0004(10) 0.0003(10) 0.0036(11) C5 0.0606(18) 0.0404(13) 0.0351(13) -0.0003(11) -0.0098(13) 0.0110(13) C21 0.0448(15) 0.0316(11) 0.0199(10) 0.0013(8) -0.0023(10) -0.0064(10) C8 0.0341(12) 0.0517(15) 0.0358(13) 0.0009(12) 0.0048(11) -0.0086(12) C36 0.0365(13) 0.0396(13) 0.0310(12) 0.0007(10) 0.0039(11) 0.0024(11) C40 0.0514(15) 0.0352(12) 0.0376(13) -0.0017(11) -0.0032(13) 0.0015(12) C17 0.0499(16) 0.0364(12) 0.0388(14) -0.0094(11) -0.0024(13) 0.0044(11) C4 0.0732(19) 0.0316(12) 0.0379(13) 0.0050(10) -0.0105(16) -0.0069(14) C1 0.0365(12) 0.0300(10) 0.0208(9) 0.0000(8) -0.0046(10) -0.0045(9) C33 0.0398(14) 0.0476(14) 0.0343(13) -0.0014(11) 0.0065(11) -0.0080(12) C39 0.0681(19) 0.0341(13) 0.0493(16) -0.0049(12) 0.0018(16) 0.0051(13) C19 0.0489(15) 0.0500(15) 0.0271(12) 0.0082(11) -0.0016(12) 0.0051(13) C18 0.0524(17) 0.0358(13) 0.0446(15) 0.0031(11) -0.0039(14) 0.0099(12) C32 0.0297(12) 0.0551(15) 0.0466(15) -0.0044(12) -0.0038(12) -0.0014(12) C16 0.0368(12) 0.0378(12) 0.0271(11) -0.0034(9) -0.0025(11) -0.0007(10) C12 0.0273(12) 0.0485(14) 0.0637(18) -0.0059(14) 0.0040(14) -0.0034(11) C26 0.0498(16) 0.0374(13) 0.0273(11) -0.0037(10) -0.0081(12) 0.0052(11) C30 0.0386(13) 0.0503(14) 0.0302(12) 0.0064(12) -0.0025(11) -0.0012(12) C34 0.0380(13) 0.0394(12) 0.0251(11) 0.0014(10) -0.0020(11) -0.0034(11) C7 0.0391(14) 0.0516(15) 0.0436(15) -0.0022(13) 0.0027(13) 0.0103(13) C3 0.0547(16) 0.0424(13) 0.0271(11) 0.0045(10) -0.0044(12) -0.0170(12) C25 0.088(2) 0.0370(14) 0.0326(13) -0.0028(11) -0.0139(16) 0.0101(16) C11 0.0345(13) 0.0504(14) 0.0489(15) -0.0063(12) -0.0067(13) 0.0036(12) C22 0.0524(16) 0.0461(14) 0.0253(11) -0.0011(11) -0.0036(12) -0.0181(13) C37 0.0404(14) 0.0484(14) 0.0380(13) 0.0102(12) 0.0038(12) 0.0105(12) C31 0.0382(14) 0.0626(17) 0.0397(13) 0.0090(13) -0.0117(12) 0.0009(13) C24 0.119(3) 0.0303(13) 0.0390(15) -0.0010(12) -0.0163(19) -0.0110(18) C6 0.0421(14) 0.0431(13) 0.0241(11) -0.0019(10) -0.0051(11) 0.0030(11) C27 0.0452(16) 0.0505(16) 0.0475(16) -0.0074(13) -0.0005(13) 0.0115(13) C14 0.0323(12) 0.0466(14) 0.0325(13) 0.0040(11) 0.0020(11) -0.0001(11) C28 0.0425(16) 0.077(2) 0.0382(15) -0.0016(14) 0.0037(13) -0.0231(15) C23 0.092(3) 0.0520(17) 0.0295(13) 0.0045(13) -0.0058(16) -0.0375(18) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 P2 O2 1.4914(16) . ? P2 N2 1.6478(19) . ? P2 C35 1.804(2) . ? P2 C29 1.809(3) . ? P1 O1 1.4901(16) . ? P1 N1 1.6455(19) . ? P1 C15 1.796(2) . ? P1 C9 1.809(3) . ? N1 C1 1.446(3) . ? N1 H1 0.8600 . ? C9 C10 1.394(3) . ? C9 C14 1.399(3) . ? N2 C21 1.441(3) . ? N2 H2 0.8600 . ? C15 C16 1.395(3) . ? C15 C20 1.408(3) . ? C38 C37 1.377(4) . ? C38 C39 1.389(4) . ? C38 H38 0.9300 . ? C29 C30 1.389(3) . ? C29 C34 1.392(3) . ? C35 C36 1.386(4) . ? C35 C40 1.398(3) . ? C10 C11 1.379(4) . ? C10 H10 0.9300 . ? C13 C14 1.380(4) . ? C13 C12 1.381(4) . ? C13 H13 0.9300 . ? C2 C3 1.396(4) . ? C2 C1 1.402(3) . ? C2 C8 1.502(4) . ? C20 C19 1.384(4) . ? C20 H20 0.9300 . ? C5 C4 1.379(4) . ? C5 C6 1.394(4) . ? C5 H5 0.9300 . ? C21 C22 1.396(4) . ? C21 C26 1.398(4) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C36 C37 1.392(4) . ? C36 H36 0.9300 . ? C40 C39 1.381(4) . ? C40 H40 0.9300 . ? C17 C16 1.374(4) . ? C17 C18 1.395(4) . ? C17 H17 0.9300 . ? C4 C3 1.380(4) . ? C4 H4 0.9300 . ? C1 C6 1.395(4) . ? C33 C34 1.376(4) . ? C33 C32 1.382(4) . ? C33 H33 0.9300 . ? C39 H39 0.9300 . ? C19 C18 1.374(4) . ? C19 H19 0.9300 . ? C18 H18 0.9300 . ? C32 C31 1.374(4) . ? C32 H32 0.9300 . ? C16 H16 0.9300 . ? C12 C11 1.381(4) . ? C12 H12 0.9300 . ? C26 C25 1.400(4) . ? C26 C27 1.504(4) . ? C30 C31 1.400(4) . ? C30 H30 0.9300 . ? C34 H34 0.9300 . ? C7 C6 1.513(4) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C3 H3 0.9300 . ? C25 C24 1.370(5) . ? C25 H25 0.9300 . ? C11 H11 0.9300 . ? C22 C23 1.405(4) . ? C22 C28 1.493(4) . ? C37 H37 0.9300 . ? C31 H31 0.9300 . ? C24 C23 1.374(5) . ? C24 H24 0.9300 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C14 H14 0.9300 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C23 H23 0.9300 . ? 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 O2 P2 N2 111.98(9) . . ? O2 P2 C35 113.26(10) . . ? N2 P2 C35 105.89(10) . . ? O2 P2 C29 110.80(11) . . ? N2 P2 C29 109.93(10) . . ? C35 P2 C29 104.62(11) . . ? O1 P1 N1 113.46(10) . . ? O1 P1 C15 112.47(10) . . ? N1 P1 C15 105.85(10) . . ? O1 P1 C9 109.87(10) . . ? N1 P1 C9 109.17(10) . . ? C15 P1 C9 105.65(11) . . ? C1 N1 P1 124.30(14) . . ? C1 N1 H1 117.8 . . ? P1 N1 H1 117.8 . . ? C10 C9 C14 119.3(2) . . ? C10 C9 P1 118.76(18) . . ? C14 C9 P1 121.92(19) . . ? C21 N2 P2 119.04(15) . . ? C21 N2 H2 120.5 . . ? P2 N2 H2 120.5 . . ? C16 C15 C20 118.4(2) . . ? C16 C15 P1 117.82(18) . . ? C20 C15 P1 123.73(18) . . ? C37 C38 C39 120.5(2) . . ? C37 C38 H38 119.7 . . ? C39 C38 H38 119.7 . . ? C30 C29 C34 119.4(2) . . ? C30 C29 P2 120.94(19) . . ? C34 C29 P2 119.66(18) . . ? C36 C35 C40 119.5(2) . . ? C36 C35 P2 123.95(19) . . ? C40 C35 P2 116.47(18) . . ? C11 C10 C9 120.0(3) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C14 C13 C12 120.4(3) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C3 C2 C1 118.3(2) . . ? C3 C2 C8 119.9(2) . . ? C1 C2 C8 121.9(2) . . ? C19 C20 C15 119.9(2) . . ? C19 C20 H20 120.0 . . ? C15 C20 H20 120.0 . . ? C4 C5 C6 120.9(3) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C22 C21 C26 121.8(2) . . ? C22 C21 N2 118.0(2) . . ? C26 C21 N2 120.2(2) . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C35 C36 C37 120.2(2) . . ? C35 C36 H36 119.9 . . ? C37 C36 H36 119.9 . . ? C39 C40 C35 120.3(3) . . ? C39 C40 H40 119.9 . . ? C35 C40 H40 119.9 . . ? C16 C17 C18 119.8(2) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C5 C4 C3 120.3(2) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C6 C1 C2 121.5(2) . . ? C6 C1 N1 120.0(2) . . ? C2 C1 N1 118.4(2) . . ? C34 C33 C32 120.2(3) . . ? C34 C33 H33 119.9 . . ? C32 C33 H33 119.9 . . ? C40 C39 C38 119.7(3) . . ? C40 C39 H39 120.2 . . ? C38 C39 H39 120.2 . . ? C18 C19 C20 120.8(2) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? C19 C18 C17 119.9(2) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C31 C32 C33 119.8(2) . . ? C31 C32 H32 120.1 . . ? C33 C32 H32 120.1 . . ? C17 C16 C15 121.1(2) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C11 C12 C13 119.9(2) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C21 C26 C25 118.3(3) . . ? C21 C26 C27 122.0(2) . . ? C25 C26 C27 119.7(3) . . ? C29 C30 C31 119.3(2) . . ? C29 C30 H30 120.3 . . ? C31 C30 H30 120.3 . . ? C33 C34 C29 120.6(2) . . ? C33 C34 H34 119.7 . . ? C29 C34 H34 119.7 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C3 C2 120.7(3) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C24 C25 C26 121.0(3) . . ? C24 C25 H25 119.5 . . ? C26 C25 H25 119.5 . . ? C10 C11 C12 120.5(3) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C21 C22 C23 117.1(3) . . ? C21 C22 C28 122.1(2) . . ? C23 C22 C28 120.7(3) . . ? C38 C37 C36 119.9(3) . . ? C38 C37 H37 120.1 . . ? C36 C37 H37 120.1 . . ? C32 C31 C30 120.7(3) . . ? C32 C31 H31 119.7 . . ? C30 C31 H31 119.7 . . ? C25 C24 C23 119.9(3) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C5 C6 C1 118.3(3) . . ? C5 C6 C7 120.2(3) . . ? C1 C6 C7 121.5(2) . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C13 C14 C9 119.9(3) . . ? C13 C14 H14 120.1 . . ? C9 C14 H14 120.1 . . ? C22 C28 H28A 109.5 . . ? C22 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C22 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C24 C23 C22 121.8(3) . . ? C24 C23 H23 119.1 . . ? C22 C23 H23 119.1 . . ? 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 N1 C1 -25.8(2) . . . . ? C15 P1 N1 C1 -149.62(19) . . . . ? C9 P1 N1 C1 97.1(2) . . . . ? O1 P1 C9 C10 9.8(2) . . . . ? N1 P1 C9 C10 -115.23(19) . . . . ? C15 P1 C9 C10 131.34(19) . . . . ? O1 P1 C9 C14 -170.6(2) . . . . ? N1 P1 C9 C14 64.3(2) . . . . ? C15 P1 C9 C14 -49.1(2) . . . . ? O2 P2 N2 C21 -31.7(2) . . . . ? C35 P2 N2 C21 -155.55(19) . . . . ? C29 P2 N2 C21 92.0(2) . . . . ? O1 P1 C15 C16 20.3(2) . . . . ? N1 P1 C15 C16 144.71(18) . . . . ? C9 P1 C15 C16 -99.6(2) . . . . ? O1 P1 C15 C20 -159.6(2) . . . . ? N1 P1 C15 C20 -35.2(2) . . . . ? C9 P1 C15 C20 80.5(2) . . . . ? O2 P2 C29 C30 4.7(2) . . . . ? N2 P2 C29 C30 -119.6(2) . . . . ? C35 P2 C29 C30 127.1(2) . . . . ? O2 P2 C29 C34 -177.48(18) . . . . ? N2 P2 C29 C34 58.2(2) . . . . ? C35 P2 C29 C34 -55.1(2) . . . . ? O2 P2 C35 C36 -116.6(2) . . . . ? N2 P2 C35 C36 6.4(2) . . . . ? C29 P2 C35 C36 122.6(2) . . . . ? O2 P2 C35 C40 59.5(2) . . . . ? N2 P2 C35 C40 -177.40(19) . . . . ? C29 P2 C35 C40 -61.3(2) . . . . ? C14 C9 C10 C11 0.0(4) . . . . ? P1 C9 C10 C11 179.6(2) . . . . ? C16 C15 C20 C19 0.3(4) . . . . ? P1 C15 C20 C19 -179.8(2) . . . . ? P2 N2 C21 C22 84.1(3) . . . . ? P2 N2 C21 C26 -97.1(2) . . . . ? C40 C35 C36 C37 -0.1(4) . . . . ? P2 C35 C36 C37 176.0(2) . . . . ? C36 C35 C40 C39 0.9(4) . . . . ? P2 C35 C40 C39 -175.4(2) . . . . ? C6 C5 C4 C3 1.6(4) . . . . ? C3 C2 C1 C6 1.0(3) . . . . ? C8 C2 C1 C6 -177.9(2) . . . . ? C3 C2 C1 N1 177.0(2) . . . . ? C8 C2 C1 N1 -1.9(3) . . . . ? P1 N1 C1 C6 -100.8(2) . . . . ? P1 N1 C1 C2 83.1(3) . . . . ? C35 C40 C39 C38 -1.2(4) . . . . ? C37 C38 C39 C40 0.7(5) . . . . ? C15 C20 C19 C18 -0.2(4) . . . . ? C20 C19 C18 C17 -0.2(5) . . . . ? C16 C17 C18 C19 0.5(5) . . . . ? C34 C33 C32 C31 0.3(4) . . . . ? C18 C17 C16 C15 -0.4(4) . . . . ? C20 C15 C16 C17 0.0(4) . . . . ? P1 C15 C16 C17 -179.9(2) . . . . ? C14 C13 C12 C11 0.4(4) . . . . ? C22 C21 C26 C25 -2.9(4) . . . . ? N2 C21 C26 C25 178.4(2) . . . . ? C22 C21 C26 C27 175.8(2) . . . . ? N2 C21 C26 C27 -3.0(4) . . . . ? C34 C29 C30 C31 -1.0(4) . . . . ? P2 C29 C30 C31 176.8(2) . . . . ? C32 C33 C34 C29 -0.8(4) . . . . ? C30 C29 C34 C33 1.1(4) . . . . ? P2 C29 C34 C33 -176.7(2) . . . . ? C5 C4 C3 C2 0.6(4) . . . . ? C1 C2 C3 C4 -1.8(4) . . . . ? C8 C2 C3 C4 177.1(2) . . . . ? C21 C26 C25 C24 0.2(4) . . . . ? C27 C26 C25 C24 -178.6(3) . . . . ? C9 C10 C11 C12 0.0(4) . . . . ? C13 C12 C11 C10 -0.2(4) . . . . ? C26 C21 C22 C23 3.6(4) . . . . ? N2 C21 C22 C23 -177.7(2) . . . . ? C26 C21 C22 C28 -175.5(2) . . . . ? N2 C21 C22 C28 3.3(4) . . . . ? C39 C38 C37 C36 0.1(4) . . . . ? C35 C36 C37 C38 -0.4(4) . . . . ? C33 C32 C31 C30 -0.2(5) . . . . ? C29 C30 C31 C32 0.6(5) . . . . ? C26 C25 C24 C23 1.8(4) . . . . ? C4 C5 C6 C1 -2.4(4) . . . . ? C4 C5 C6 C7 176.5(3) . . . . ? C2 C1 C6 C5 1.1(4) . . . . ? N1 C1 C6 C5 -174.9(2) . . . . ? C2 C1 C6 C7 -177.7(2) . . . . ? N1 C1 C6 C7 6.3(3) . . . . ? C12 C13 C14 C9 -0.4(4) . . . . ? C10 C9 C14 C13 0.2(4) . . . . ? P1 C9 C14 C13 -179.4(2) . . . . ? C25 C24 C23 C22 -1.1(5) . . . . ? C21 C22 C23 C24 -1.6(4) . . . . ? C28 C22 C23 C24 177.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.81 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.274 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.044 data_exp_804-2 _database_code_depnum_ccdc_archive 'CCDC 893244' #TrackingRef 'exp_804-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '4(C30 H29 Cl N P Zr), C28 H32, 4(C7 H8)' _chemical_formula_sum 'C176 H180 Cl4 N4 P4 Zr4' _chemical_formula_weight 2981.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zr Zr -0.1862 2.2449 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n m a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 14.2392(12) _cell_length_b 14.6310(18) _cell_length_c 18.0321(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3756.7(7) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.89 _cell_measurement_theta_max 70.85 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 3.682 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.42 _exptl_absorpt_correction_T_max 0.60 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'supernova Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10002 _diffrn_reflns_av_R_equivalents 0.0491 _diffrn_reflns_av_sigmaI/netI 0.0552 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.89 _diffrn_reflns_theta_max 70.85 _reflns_number_total 3695 _reflns_number_gt 2930 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP III & Olex 2.1' _computing_publication_material WinGX _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^ > 2\s(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^)+(0.0581P)^2^+4.6503P] 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 3695 _refine_ls_number_parameters 320 _refine_ls_number_restraints 260 _refine_ls_R_factor_all 0.0674 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1304 _refine_ls_wR_factor_gt 0.1186 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.045 _refine_ls_shift/su_mean 0.003 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 Zr1 Zr 0.81432(3) 0.7500 0.30788(2) 0.02506(15) Uani 1 2 d S . . P1 P 0.81726(9) 0.7500 0.45392(7) 0.0264(3) Uani 1 2 d S . . Cl2 Cl 0.65920(9) 0.7500 0.23976(8) 0.0490(4) Uani 1 2 d S . . N1 N 0.7204(3) 0.7500 0.4048(2) 0.0279(10) Uani 1 2 d S . . C4 C 0.8292(2) 0.6560(3) 0.5195(2) 0.0295(8) Uani 1 1 d . . . C1 C 0.8561(3) 0.5848(3) 0.3371(2) 0.0380(9) Uani 1 1 d . . . H1 H 0.8427 0.5614 0.3839 0.046 Uiso 1 1 calc R . . C2 C 0.7966(3) 0.5830(3) 0.2747(2) 0.0402(10) Uani 1 1 d . . . H2 H 0.7362 0.5590 0.2732 0.048 Uiso 1 1 calc R . . C3 C 0.9337(3) 0.6491(3) 0.2394(2) 0.0386(10) Uani 1 1 d . . . H3 H 0.9808 0.6750 0.2104 0.046 Uiso 1 1 calc R . . C5 C 0.9399(3) 0.6288(3) 0.3152(2) 0.0386(10) Uani 1 1 d . . . H5 H 0.9906 0.6421 0.3458 0.046 Uiso 1 1 calc R . . C6 C 0.8444(3) 0.6237(3) 0.2151(2) 0.0400(10) Uani 1 1 d . . . H6 H 0.8206 0.6322 0.1675 0.048 Uiso 1 1 calc R . . C7 C 0.5744(3) 0.6676(4) 0.4334(2) 0.0493(13) Uani 1 1 d . . . C8 C 0.7578(3) 0.6313(3) 0.5681(2) 0.0411(10) Uani 1 1 d . . . H8 H 0.6998 0.6601 0.5650 0.049 Uiso 1 1 calc R . . C9 C 0.4789(3) 0.6687(5) 0.4530(2) 0.0649(17) Uani 1 1 d . . . H9 H 0.4468 0.6139 0.4594 0.078 Uiso 1 1 calc R . . C10 C 0.6227(4) 0.7500 0.4260(3) 0.0381(14) Uani 1 2 d S . . C11 C 0.4328(5) 0.7500 0.4627(4) 0.071(3) Uani 1 2 d S . . H11 H 0.3697 0.7500 0.4760 0.085 Uiso 1 2 calc SR . . C12 C 0.7722(3) 0.5641(3) 0.6213(2) 0.0495(12) Uani 1 1 d . . . H12 H 0.7238 0.5481 0.6534 0.059 Uiso 1 1 calc R . . C13 C 0.6200(4) 0.5765(4) 0.4190(3) 0.0615(15) Uani 1 1 d . . . H13A H 0.5840 0.5291 0.4424 0.092 Uiso 1 1 calc R . . H13B H 0.6825 0.5767 0.4389 0.092 Uiso 1 1 calc R . . H13C H 0.6227 0.5656 0.3665 0.092 Uiso 1 1 calc R . . C15 C 0.9154(3) 0.6135(3) 0.5265(2) 0.0489(12) Uani 1 1 d . . . H15 H 0.9645 0.6298 0.4952 0.059 Uiso 1 1 calc R . . C16 C 0.8576(3) 0.5211(3) 0.6265(2) 0.0515(12) Uani 1 1 d . . . H16 H 0.8669 0.4751 0.6613 0.062 Uiso 1 1 calc R . . C20 C 0.9293(4) 0.5467(4) 0.5800(3) 0.0615(15) Uani 1 1 d . . . H20 H 0.9878 0.5189 0.5844 0.074 Uiso 1 1 calc R . . C3S C 0.1790(15) 0.8068(18) 0.4639(10) 0.050(3) Uani 0.25 1 d PGU A -1 H3S H 0.1627 0.8340 0.4191 0.060 Uiso 0.25 1 calc PR A -1 C2S C 0.2126(17) 0.8599(13) 0.5219(14) 0.056(3) Uani 0.25 1 d PGU A -1 H2S H 0.2188 0.9228 0.5160 0.068 Uiso 0.25 1 calc PR A -1 C1S C 0.2370(17) 0.8192(11) 0.5889(11) 0.060(3) Uani 0.25 1 d PGDU A -1 H1S H 0.2595 0.8547 0.6277 0.071 Uiso 0.25 1 calc PR A -1 C6S C 0.2277(16) 0.7252(11) 0.5977(7) 0.058(3) Uani 0.25 1 d PGDU A -1 C5S C 0.1940(17) 0.6720(11) 0.5396(9) 0.056(3) Uani 0.25 1 d PGDU A -1 H5S H 0.1878 0.6092 0.5455 0.067 Uiso 0.25 1 calc PR A -1 C4S C 0.1697(15) 0.7128(17) 0.4727(7) 0.052(3) Uani 0.25 1 d PGU A -1 H4S H 0.1472 0.6772 0.4338 0.062 Uiso 0.25 1 calc PR A -1 C6T C 0.5213(5) 0.7991(4) 0.7034(4) 0.060(2) Uani 0.50 1 d PGDU B -1 C1T C 0.5206(5) 0.7667(5) 0.7758(3) 0.070(3) Uani 0.50 1 d PGU B -1 H1T H 0.5187 0.8076 0.8153 0.084 Uiso 0.50 1 calc PR B -1 C2T C 0.5227(5) 0.6732(5) 0.7893(3) 0.079(3) Uani 0.50 1 d PGU B -1 H2T H 0.5222 0.6515 0.8378 0.095 Uiso 0.50 1 calc PR B -1 C3T C 0.5255(7) 0.6120(4) 0.7304(5) 0.072(3) Uani 0.50 1 d PGU B -1 H3T H 0.5269 0.5495 0.7394 0.086 Uiso 0.50 1 calc PR B -1 C4T C 0.5262(6) 0.6444(5) 0.6579(4) 0.066(2) Uani 0.50 1 d PGU B -1 H4T H 0.5281 0.6035 0.6184 0.079 Uiso 0.50 1 calc PR B -1 C5T C 0.5241(4) 0.7379(6) 0.6444(3) 0.057(2) Uani 0.50 1 d PGU B -1 H5T H 0.5246 0.7596 0.5959 0.068 Uiso 0.50 1 calc PR B -1 C7T C 0.5172(13) 0.9006(7) 0.6885(8) 0.089(4) Uani 0.50 1 d PDU B -1 H7TA H 0.4533 0.9210 0.6915 0.134 Uiso 0.50 1 calc PR B -1 H7TB H 0.5415 0.9130 0.6399 0.134 Uiso 0.50 1 calc PR B -1 H7TC H 0.5543 0.9323 0.7248 0.134 Uiso 0.50 1 calc PR B -1 C7S C 0.2598(19) 0.6790(16) 0.6704(10) 0.068(5) Uani 0.25 1 d PDU A -1 H7SD H 0.3272 0.6788 0.6726 0.103 Uiso 0.25 1 calc PR A -1 H7SE H 0.2371 0.6172 0.6717 0.103 Uiso 0.25 1 calc PR A -1 H7SF H 0.2352 0.7121 0.7120 0.103 Uiso 0.25 1 calc PR A -1 C6S' C 0.2319(14) 0.7393(15) 0.6203(8) 0.058(3) Uani 0.25 1 d PGDU C -2 C1S' C 0.2269(18) 0.8307(13) 0.5996(12) 0.059(3) Uani 0.25 1 d PGDU C -2 H1S' H 0.2438 0.8762 0.6330 0.071 Uiso 0.25 1 calc PR C -2 C2S' C 0.1965(19) 0.8541(10) 0.5288(13) 0.056(3) Uani 0.25 1 d PGU C -2 H2S' H 0.1931 0.9153 0.5149 0.067 Uiso 0.25 1 calc PR C -2 C3S' C 0.1712(16) 0.7862(12) 0.4788(10) 0.054(3) Uani 0.25 1 d PGU C -2 H3S' H 0.1509 0.8018 0.4314 0.064 Uiso 0.25 1 calc PR C -2 C4S' C 0.1763(15) 0.6948(11) 0.4995(8) 0.057(3) Uani 0.25 1 d PGU C -2 H4S' H 0.1593 0.6493 0.4660 0.068 Uiso 0.25 1 calc PR C -2 C5S' C 0.2067(14) 0.6714(11) 0.5702(8) 0.061(3) Uani 0.25 1 d PGDU C -2 H5S' H 0.2101 0.6102 0.5841 0.073 Uiso 0.25 1 calc PR C -2 C7S' C 0.268(2) 0.726(2) 0.6998(10) 0.098(13) Uani 0.25 1 d PDU C -2 H7SA H 0.2870 0.7837 0.7199 0.146 Uiso 0.25 1 calc PR C -2 H7SB H 0.3202 0.6847 0.6995 0.146 Uiso 0.25 1 calc PR C -2 H7SC H 0.2184 0.7009 0.7299 0.146 Uiso 0.25 1 calc PR C -2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zr1 0.0171(2) 0.0321(3) 0.0259(2) 0.000 -0.00022(16) 0.000 P1 0.0206(6) 0.0330(8) 0.0255(6) 0.000 0.0001(5) 0.000 Cl2 0.0203(6) 0.0912(13) 0.0355(7) 0.000 -0.0042(5) 0.000 N1 0.018(2) 0.037(3) 0.028(2) 0.000 -0.0022(17) 0.000 C4 0.0291(19) 0.034(2) 0.0256(18) 0.0019(16) 0.0002(15) 0.0013(16) C1 0.049(2) 0.028(2) 0.037(2) -0.0006(17) 0.0046(19) 0.0059(19) C2 0.045(2) 0.036(2) 0.039(2) -0.0057(19) 0.0037(19) -0.010(2) C3 0.035(2) 0.036(2) 0.044(2) -0.0032(19) 0.0103(18) 0.0003(19) C5 0.033(2) 0.035(2) 0.048(2) -0.0040(19) -0.0004(18) 0.0115(18) C6 0.047(2) 0.038(2) 0.036(2) -0.0064(19) 0.0021(19) -0.002(2) C7 0.027(2) 0.088(4) 0.033(2) -0.002(2) 0.0009(17) -0.019(2) C8 0.033(2) 0.044(3) 0.046(2) 0.013(2) 0.0079(18) 0.0041(19) C9 0.029(2) 0.129(5) 0.037(2) 0.005(3) -0.0011(19) -0.028(3) C10 0.018(2) 0.069(4) 0.027(3) 0.000 0.003(2) 0.000 C11 0.021(3) 0.155(9) 0.036(4) 0.000 -0.003(3) 0.000 C12 0.048(3) 0.052(3) 0.048(3) 0.020(2) 0.012(2) 0.002(2) C13 0.050(3) 0.076(4) 0.059(3) 0.001(3) 0.007(2) -0.030(3) C15 0.036(2) 0.068(3) 0.042(2) 0.021(2) 0.0097(19) 0.017(2) C16 0.060(3) 0.052(3) 0.042(2) 0.014(2) 0.008(2) 0.015(2) C20 0.054(3) 0.076(4) 0.055(3) 0.024(3) 0.010(2) 0.034(3) C3S 0.037(5) 0.067(7) 0.048(6) 0.009(5) 0.012(5) -0.004(6) C2S 0.045(6) 0.073(6) 0.052(6) 0.001(5) 0.012(5) 0.000(5) C1S 0.050(5) 0.075(6) 0.054(6) 0.002(5) 0.008(5) 0.000(5) C6S 0.048(5) 0.072(7) 0.053(7) 0.007(5) 0.010(6) -0.001(5) C5S 0.042(6) 0.070(7) 0.055(8) 0.013(6) 0.006(6) -0.007(6) C4S 0.035(5) 0.068(7) 0.053(7) 0.011(6) 0.007(6) -0.006(6) C6T 0.057(5) 0.060(5) 0.064(5) 0.003(4) 0.002(4) -0.004(4) C1T 0.084(5) 0.073(7) 0.052(4) -0.006(4) 0.009(4) -0.012(5) C2T 0.092(6) 0.084(7) 0.062(5) 0.018(4) 0.003(5) -0.011(6) C3T 0.075(6) 0.064(6) 0.076(6) 0.016(4) 0.008(6) 0.005(5) C4T 0.064(5) 0.071(5) 0.063(5) 0.002(5) 0.010(5) 0.001(5) C5T 0.052(4) 0.074(5) 0.045(3) 0.010(5) -0.004(3) -0.003(6) C7T 0.102(10) 0.072(6) 0.094(10) -0.001(7) 0.013(9) 0.002(8) C7S 0.060(10) 0.086(12) 0.059(10) 0.015(8) 0.001(9) -0.012(10) C6S' 0.046(5) 0.073(7) 0.056(7) 0.007(5) 0.011(5) -0.002(5) C1S' 0.051(6) 0.075(6) 0.052(6) 0.002(5) 0.010(6) 0.000(5) C2S' 0.044(6) 0.073(6) 0.050(6) 0.002(5) 0.012(5) -0.001(5) C3S' 0.037(5) 0.070(7) 0.053(7) 0.004(5) 0.008(5) -0.002(6) C4S' 0.040(5) 0.070(7) 0.060(8) 0.007(6) 0.005(6) -0.008(6) C5S' 0.049(6) 0.072(6) 0.062(8) 0.009(6) 0.006(6) -0.009(6) C7S' 0.10(2) 0.12(4) 0.072(12) 0.023(14) -0.013(13) -0.01(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Zr1 N1 2.201(4) . ? Zr1 C5 2.522(4) 8_575 ? Zr1 C5 2.522(4) . ? Zr1 Cl2 2.5273(14) . ? Zr1 C2 2.528(4) 8_575 ? Zr1 C2 2.528(4) . ? Zr1 C6 2.529(4) 8_575 ? Zr1 C6 2.529(4) . ? Zr1 C1 2.544(4) 8_575 ? Zr1 C1 2.544(4) . ? Zr1 C3 2.568(4) 8_575 ? Zr1 C3 2.568(4) . ? P1 N1 1.640(4) . ? P1 C4 1.823(4) . ? P1 C4 1.823(4) 8_575 ? N1 C10 1.442(6) . ? C4 C15 1.381(5) . ? C4 C8 1.390(5) . ? C1 C2 1.408(6) . ? C1 C5 1.413(6) . ? C2 C6 1.405(6) . ? C3 C6 1.396(6) . ? C3 C5 1.401(6) . ? C7 C10 1.394(5) . ? C7 C9 1.406(6) . ? C7 C13 1.505(7) . ? C8 C12 1.388(6) . ? C9 C11 1.370(7) . ? C10 C7 1.394(5) 8_575 ? C11 C9 1.370(7) 8_575 ? C12 C16 1.372(6) . ? C15 C20 1.387(6) . ? C16 C20 1.374(6) . ? C3S C2S 1.3900 . ? C3S C4S 1.3900 . ? C2S C1S 1.3900 . ? C1S C6S 1.3900 . ? C6S C5S 1.3900 . ? C6S C7S 1.544(9) . ? C5S C4S 1.3900 . ? C6T C1T 1.3900 . ? C6T C5T 1.3900 . ? C6T C7T 1.510(8) . ? C1T C2T 1.3900 . ? C2T C3T 1.3900 . ? C3T C4T 1.3900 . ? C4T C5T 1.3900 . ? C6S' C1S' 1.3900 . ? C6S' C5S' 1.3900 . ? C6S' C7S' 1.535(9) . ? C1S' C2S' 1.3900 . ? C2S' C3S' 1.3900 . ? C3S' C4S' 1.3900 . ? C4S' C5S' 1.3900 . ? 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 N1 Zr1 C5 112.93(12) . 8_575 ? N1 Zr1 C5 112.93(12) . . ? C5 Zr1 C5 89.4(2) 8_575 . ? N1 Zr1 Cl2 81.64(11) . . ? C5 Zr1 Cl2 130.18(10) 8_575 . ? C5 Zr1 Cl2 130.18(10) . . ? N1 Zr1 C2 97.31(10) . 8_575 ? C5 Zr1 C2 53.37(14) 8_575 8_575 ? C5 Zr1 C2 139.69(14) . 8_575 ? Cl2 Zr1 C2 78.35(10) . 8_575 ? N1 Zr1 C2 97.31(10) . . ? C5 Zr1 C2 139.69(14) 8_575 . ? C5 Zr1 C2 53.37(14) . . ? Cl2 Zr1 C2 78.35(10) . . ? C2 Zr1 C2 150.3(2) 8_575 . ? N1 Zr1 C6 128.92(11) . 8_575 ? C5 Zr1 C6 53.20(14) 8_575 8_575 ? C5 Zr1 C6 115.35(14) . 8_575 ? Cl2 Zr1 C6 80.00(10) . 8_575 ? C2 Zr1 C6 32.25(13) 8_575 8_575 ? C2 Zr1 C6 124.50(14) . 8_575 ? N1 Zr1 C6 128.92(11) . . ? C5 Zr1 C6 115.35(14) 8_575 . ? C5 Zr1 C6 53.20(14) . . ? Cl2 Zr1 C6 80.00(10) . . ? C2 Zr1 C6 124.50(14) 8_575 . ? C2 Zr1 C6 32.25(13) . . ? C6 Zr1 C6 93.9(2) 8_575 . ? N1 Zr1 C1 88.70(10) . 8_575 ? C5 Zr1 C1 32.40(13) 8_575 8_575 ? C5 Zr1 C1 119.44(15) . 8_575 ? Cl2 Zr1 C1 107.75(10) . 8_575 ? C2 Zr1 C1 32.23(14) 8_575 8_575 ? C2 Zr1 C1 172.08(14) . 8_575 ? C6 Zr1 C1 53.39(14) 8_575 8_575 ? C6 Zr1 C1 142.34(14) . 8_575 ? N1 Zr1 C1 88.70(10) . . ? C5 Zr1 C1 119.44(15) 8_575 . ? C5 Zr1 C1 32.40(13) . . ? Cl2 Zr1 C1 107.75(10) . . ? C2 Zr1 C1 172.08(14) 8_575 . ? C2 Zr1 C1 32.23(14) . . ? C6 Zr1 C1 142.34(14) 8_575 . ? C6 Zr1 C1 53.39(14) . . ? C1 Zr1 C1 143.6(2) 8_575 . ? N1 Zr1 C3 141.66(10) . 8_575 ? C5 Zr1 C3 31.94(13) 8_575 8_575 ? C5 Zr1 C3 87.69(14) . 8_575 ? Cl2 Zr1 C3 110.18(10) . 8_575 ? C2 Zr1 C3 52.89(13) 8_575 8_575 ? C2 Zr1 C3 120.51(14) . 8_575 ? C6 Zr1 C3 31.78(13) 8_575 8_575 ? C6 Zr1 C3 89.41(14) . 8_575 ? C1 Zr1 C3 53.06(13) 8_575 8_575 ? C1 Zr1 C3 119.41(14) . 8_575 ? N1 Zr1 C3 141.66(10) . . ? C5 Zr1 C3 87.69(14) 8_575 . ? C5 Zr1 C3 31.94(13) . . ? Cl2 Zr1 C3 110.18(10) . . ? C2 Zr1 C3 120.51(14) 8_575 . ? C2 Zr1 C3 52.89(13) . . ? C6 Zr1 C3 89.41(14) 8_575 . ? C6 Zr1 C3 31.78(13) . . ? C1 Zr1 C3 119.41(14) 8_575 . ? C1 Zr1 C3 53.06(13) . . ? C3 Zr1 C3 70.16(19) 8_575 . ? N1 P1 C4 115.43(15) . . ? N1 P1 C4 115.43(15) . 8_575 ? C4 P1 C4 98.0(2) . 8_575 ? N1 P1 Zr1 56.39(15) . . ? C4 P1 Zr1 130.58(12) . . ? C4 P1 Zr1 130.58(12) 8_575 . ? C10 N1 P1 132.0(4) . . ? C10 N1 Zr1 142.8(3) . . ? P1 N1 Zr1 85.26(18) . . ? C15 C4 C8 118.4(4) . . ? C15 C4 P1 118.8(3) . . ? C8 C4 P1 122.5(3) . . ? C2 C1 C5 107.0(4) . . ? C2 C1 Zr1 73.2(2) . . ? C5 C1 Zr1 72.9(2) . . ? C6 C2 C1 108.3(4) . . ? C6 C2 Zr1 73.9(2) . . ? C1 C2 Zr1 74.5(2) . . ? C6 C3 C5 107.9(4) . . ? C6 C3 Zr1 72.6(2) . . ? C5 C3 Zr1 72.2(2) . . ? C3 C5 C1 108.5(4) . . ? C3 C5 Zr1 75.8(2) . . ? C1 C5 Zr1 74.7(2) . . ? C3 C6 C2 108.3(4) . . ? C3 C6 Zr1 75.6(2) . . ? C2 C6 Zr1 73.8(2) . . ? C10 C7 C9 119.5(5) . . ? C10 C7 C13 122.4(4) . . ? C9 C7 C13 118.1(5) . . ? C12 C8 C4 120.7(4) . . ? C11 C9 C7 120.3(6) . . ? C7 C10 C7 119.7(5) 8_575 . ? C7 C10 N1 120.1(3) 8_575 . ? C7 C10 N1 120.1(3) . . ? C9 C11 C9 120.6(6) 8_575 . ? C16 C12 C8 120.2(4) . . ? C4 C15 C20 120.5(4) . . ? C20 C16 C12 119.4(4) . . ? C16 C20 C15 120.7(4) . . ? C2S C3S C4S 120.0 . . ? C3S C2S C1S 120.0 . . ? C6S C1S C2S 120.0 . . ? C1S C6S C5S 120.0 . . ? C1S C6S C7S 120.2(7) . . ? C5S C6S C7S 119.8(7) . . ? C4S C5S C6S 120.0 . . ? C5S C4S C3S 120.0 . . ? C1T C6T C5T 120.0 . . ? C1T C6T C7T 120.1(9) . . ? C5T C6T C7T 119.9(9) . . ? C2T C1T C6T 120.0 . . ? C1T C2T C3T 120.0 . . ? C4T C3T C2T 120.0 . . ? C5T C4T C3T 120.0 . . ? C4T C5T C6T 120.0 . . ? C1S' C6S' C5S' 120.0 . . ? C1S' C6S' C7S' 113.1(12) . . ? C5S' C6S' C7S' 126.9(12) . . ? C2S' C1S' C6S' 120.0 . . ? C1S' C2S' C3S' 120.0 . . ? C2S' C3S' C4S' 120.0 . . ? C3S' C4S' C5S' 120.0 . . ? C4S' C5S' C6S' 120.0 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 70.85 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.505 _refine_diff_density_min -1.291 _refine_diff_density_rms 0.090 data_exp_854 _database_code_depnum_ccdc_archive 'CCDC 893245' #TrackingRef 'exp_854.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H20 N P Se' _chemical_formula_sum 'C20 H20 N P Se' _chemical_formula_weight 384.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 43' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x, z+3/4' '-x, -y, z+1/2' 'y, -x, z+1/4' _cell_length_a 11.8869(2) _cell_length_b 11.8869(2) _cell_length_c 12.6006(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1780.44(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.72 _cell_measurement_theta_max 70.80 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 3.676 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.470 _exptl_absorpt_correction_T_max 0.599 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'supernova Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3497 _diffrn_reflns_av_R_equivalents 0.0169 _diffrn_reflns_av_sigmaI/netI 0.0258 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.72 _diffrn_reflns_theta_max 70.80 _reflns_number_total 2336 _reflns_number_gt 2302 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP III & Olex 2.1' _computing_publication_material WinGX _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^ > 2\s(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^)+(0.0607P)^2^+0.1363P] 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 -0.04(2) _refine_ls_number_reflns 2336 _refine_ls_number_parameters 210 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0296 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0786 _refine_ls_wR_factor_gt 0.0783 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 Se1 Se 0.05285(2) 0.45036(3) 0.88278(3) 0.03235(13) Uani 1 1 d . . . P1 P -0.04182(6) 0.50170(6) 0.75048(7) 0.02173(17) Uani 1 1 d . . . N1 N 0.0208(2) 0.4657(2) 0.6381(2) 0.0245(5) Uani 1 1 d . . . H8BA H -0.0159 0.4763 0.5801 0.029 Uiso 1 1 calc R . . C1 C 0.1319(2) 0.4181(2) 0.6296(3) 0.0228(6) Uani 1 1 d . . . C2 C 0.1459(3) 0.3011(3) 0.6365(3) 0.0293(6) Uani 1 1 d . . . C3 C 0.2530(3) 0.2570(3) 0.6212(3) 0.0344(7) Uani 1 1 d . . . H17 H 0.2634 0.1795 0.6237 0.041 Uiso 1 1 calc R . . C4 C 0.3443(3) 0.3261(3) 0.6021(3) 0.0357(8) Uani 1 1 d . . . H23 H 0.4153 0.2951 0.5917 0.043 Uiso 1 1 calc R . . C5 C 0.3295(3) 0.4423(3) 0.5985(3) 0.0322(7) Uani 1 1 d . . . H20 H 0.3914 0.4887 0.5874 0.039 Uiso 1 1 calc R . . C6 C 0.2238(3) 0.4896(3) 0.6111(3) 0.0263(7) Uani 1 1 d . . . C7 C 0.2070(3) 0.6155(3) 0.6033(3) 0.0327(8) Uani 1 1 d . . . H19A H 0.1639 0.6327 0.5410 0.049 Uiso 1 1 calc R . . H19B H 0.2789 0.6520 0.5991 0.049 Uiso 1 1 calc R . . H19C H 0.1676 0.6418 0.6651 0.049 Uiso 1 1 calc R . . C8 C 0.0476(3) 0.2242(3) 0.6560(4) 0.0423(10) Uani 1 1 d . . . H18A H 0.0724 0.1474 0.6530 0.063 Uiso 1 1 calc R . . H18B H -0.0087 0.2366 0.6027 0.063 Uiso 1 1 calc R . . H18C H 0.0163 0.2393 0.7248 0.063 Uiso 1 1 calc R . . C9 C -0.1812(2) 0.4407(2) 0.7444(3) 0.0232(6) Uani 1 1 d . . . C10 C -0.2189(3) 0.3815(3) 0.6563(3) 0.0278(7) Uani 1 1 d . . . H8 H -0.1723 0.3724 0.5976 0.033 Uiso 1 1 calc R . . C11 C -0.3272(3) 0.3358(3) 0.6565(3) 0.0321(8) Uani 1 1 d . . . H14 H -0.3528 0.2961 0.5977 0.039 Uiso 1 1 calc R . . C12 C -0.3963(3) 0.3492(3) 0.7433(3) 0.0311(7) Uani 1 1 d . . . H21 H -0.4680 0.3178 0.7431 0.037 Uiso 1 1 calc R . . C13 C -0.3594(3) 0.4096(3) 0.8312(3) 0.0315(7) Uani 1 1 d . . . H13 H -0.4065 0.4187 0.8896 0.038 Uiso 1 1 calc R . . C14 C -0.2521(3) 0.4562(3) 0.8318(3) 0.0281(7) Uani 1 1 d . . . H7 H -0.2276 0.4975 0.8900 0.034 Uiso 1 1 calc R . . C15 C -0.0717(2) 0.6520(2) 0.7459(3) 0.0264(6) Uani 1 1 d . . . C16 C -0.1128(3) 0.6986(3) 0.6521(3) 0.0336(8) Uani 1 1 d . . . H10 H -0.1206 0.6540 0.5919 0.040 Uiso 1 1 calc R . . C17 C -0.1420(3) 0.8118(3) 0.6483(4) 0.0423(9) Uani 1 1 d . . . H16 H -0.1702 0.8429 0.5860 0.051 Uiso 1 1 calc R . . C18 C -0.1290(3) 0.8778(3) 0.7379(4) 0.0469(11) Uani 1 1 d . . . H22 H -0.1469 0.9539 0.7350 0.056 Uiso 1 1 calc R . . C19 C -0.0900(3) 0.8323(3) 0.8311(4) 0.0469(11) Uani 1 1 d . . . H15 H -0.0826 0.8772 0.8911 0.056 Uiso 1 1 calc R . . C20 C -0.0614(3) 0.7181(3) 0.8356(4) 0.0370(8) Uani 1 1 d . . . H9 H -0.0356 0.6869 0.8987 0.044 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 Se1 0.02565(17) 0.0526(2) 0.01883(19) 0.00033(16) -0.00186(15) 0.00879(13) P1 0.0198(3) 0.0273(4) 0.0181(4) -0.0019(3) -0.0012(3) 0.0023(3) N1 0.0221(12) 0.0340(12) 0.0174(13) 0.0012(12) -0.0030(11) 0.0042(9) C1 0.0253(13) 0.0271(13) 0.0160(13) -0.0012(13) -0.0013(12) 0.0025(10) C2 0.0338(16) 0.0307(14) 0.0234(15) -0.0021(15) 0.0004(15) 0.0044(12) C3 0.0419(18) 0.0337(15) 0.0276(17) -0.0043(16) -0.0023(16) 0.0122(12) C4 0.0312(16) 0.0477(19) 0.0281(19) -0.0064(16) -0.0022(14) 0.0153(14) C5 0.0232(14) 0.0491(19) 0.0242(17) -0.0022(16) 0.0002(13) 0.0003(13) C6 0.0295(14) 0.0318(15) 0.0175(17) -0.0012(13) -0.0003(12) 0.0011(11) C7 0.0357(16) 0.0317(16) 0.0306(19) -0.0025(15) -0.0032(15) -0.0058(13) C8 0.049(2) 0.0270(15) 0.051(3) 0.0032(16) 0.0053(19) -0.0002(14) C9 0.0223(13) 0.0236(12) 0.0238(15) 0.0063(13) 0.0016(13) 0.0015(10) C10 0.0268(15) 0.0306(14) 0.0260(19) 0.0018(13) 0.0000(13) 0.0019(11) C11 0.0340(17) 0.0317(15) 0.031(2) -0.0016(14) -0.0056(14) -0.0057(12) C12 0.0259(14) 0.0334(15) 0.0340(19) 0.0051(15) -0.0002(14) -0.0053(11) C13 0.0261(15) 0.0382(16) 0.0301(18) 0.0047(15) 0.0046(14) -0.0007(13) C14 0.0275(15) 0.0320(15) 0.0247(17) -0.0031(14) -0.0017(14) -0.0001(12) C15 0.0203(12) 0.0270(14) 0.0320(17) -0.0050(15) 0.0025(13) 0.0004(11) C16 0.0334(16) 0.0298(15) 0.038(2) -0.0037(15) 0.0034(15) 0.0054(12) C17 0.0408(19) 0.0353(17) 0.051(3) 0.0075(19) 0.0120(18) 0.0092(14) C18 0.0351(17) 0.0263(16) 0.079(3) -0.006(2) 0.011(2) 0.0014(13) C19 0.0370(18) 0.0342(18) 0.069(3) -0.026(2) 0.003(2) -0.0016(14) C20 0.0274(15) 0.0426(19) 0.041(2) -0.0123(17) -0.0028(15) 0.0024(13) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Se1 P1 2.1019(8) . ? P1 N1 1.656(3) . ? P1 C9 1.811(3) . ? P1 C15 1.822(3) . ? N1 C1 1.441(4) . ? N1 H8BA 0.8600 . ? C1 C2 1.403(4) . ? C1 C6 1.403(4) . ? C2 C3 1.391(5) . ? C2 C8 1.505(5) . ? C3 C4 1.382(5) . ? C3 H17 0.9300 . ? C4 C5 1.393(5) . ? C4 H23 0.9300 . ? C5 C6 1.386(4) . ? C5 H20 0.9300 . ? C6 C7 1.513(4) . ? C7 H19A 0.9600 . ? C7 H19B 0.9600 . ? C7 H19C 0.9600 . ? C8 H18A 0.9600 . ? C8 H18B 0.9600 . ? C8 H18C 0.9600 . ? C9 C10 1.389(5) . ? C9 C14 1.398(5) . ? C10 C11 1.398(5) . ? C10 H8 0.9300 . ? C11 C12 1.377(5) . ? C11 H14 0.9300 . ? C12 C13 1.391(5) . ? C12 H21 0.9300 . ? C13 C14 1.391(5) . ? C13 H13 0.9300 . ? C14 H7 0.9300 . ? C15 C20 1.382(5) . ? C15 C16 1.394(5) . ? C16 C17 1.390(5) . ? C16 H10 0.9300 . ? C17 C18 1.384(7) . ? C17 H16 0.9300 . ? C18 C19 1.373(8) . ? C18 H22 0.9300 . ? C19 C20 1.401(5) . ? C19 H15 0.9300 . ? C20 H9 0.9300 . ? 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 N1 P1 C9 105.78(15) . . ? N1 P1 C15 108.29(15) . . ? C9 P1 C15 102.28(13) . . ? N1 P1 Se1 111.27(10) . . ? C9 P1 Se1 114.02(11) . . ? C15 P1 Se1 114.47(12) . . ? C1 N1 P1 125.2(2) . . ? C1 N1 H8BA 117.4 . . ? P1 N1 H8BA 117.4 . . ? C2 C1 C6 121.2(3) . . ? C2 C1 N1 119.6(3) . . ? C6 C1 N1 119.2(3) . . ? C3 C2 C1 118.3(3) . . ? C3 C2 C8 120.3(3) . . ? C1 C2 C8 121.4(3) . . ? C4 C3 C2 121.3(3) . . ? C4 C3 H17 119.4 . . ? C2 C3 H17 119.4 . . ? C3 C4 C5 119.8(3) . . ? C3 C4 H23 120.1 . . ? C5 C4 H23 120.1 . . ? C6 C5 C4 120.8(3) . . ? C6 C5 H20 119.6 . . ? C4 C5 H20 119.6 . . ? C5 C6 C1 118.6(3) . . ? C5 C6 C7 120.9(3) . . ? C1 C6 C7 120.5(3) . . ? C6 C7 H19A 109.5 . . ? C6 C7 H19B 109.5 . . ? H19A C7 H19B 109.5 . . ? C6 C7 H19C 109.5 . . ? H19A C7 H19C 109.5 . . ? H19B C7 H19C 109.5 . . ? C2 C8 H18A 109.5 . . ? C2 C8 H18B 109.5 . . ? H18A C8 H18B 109.5 . . ? C2 C8 H18C 109.5 . . ? H18A C8 H18C 109.5 . . ? H18B C8 H18C 109.5 . . ? C10 C9 C14 120.2(3) . . ? C10 C9 P1 122.1(2) . . ? C14 C9 P1 117.7(2) . . ? C9 C10 C11 119.5(3) . . ? C9 C10 H8 120.3 . . ? C11 C10 H8 120.3 . . ? C12 C11 C10 120.4(3) . . ? C12 C11 H14 119.8 . . ? C10 C11 H14 119.8 . . ? C11 C12 C13 120.3(3) . . ? C11 C12 H21 119.9 . . ? C13 C12 H21 119.9 . . ? C12 C13 C14 119.9(3) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C9 119.7(3) . . ? C13 C14 H7 120.1 . . ? C9 C14 H7 120.1 . . ? C20 C15 C16 119.9(3) . . ? C20 C15 P1 120.9(3) . . ? C16 C15 P1 119.0(3) . . ? C17 C16 C15 120.1(4) . . ? C17 C16 H10 120.0 . . ? C15 C16 H10 120.0 . . ? C18 C17 C16 119.6(4) . . ? C18 C17 H16 120.2 . . ? C16 C17 H16 120.2 . . ? C19 C18 C17 120.8(3) . . ? C19 C18 H22 119.6 . . ? C17 C18 H22 119.6 . . ? C18 C19 C20 119.9(4) . . ? C18 C19 H15 120.1 . . ? C20 C19 H15 120.1 . . ? C15 C20 C19 119.8(4) . . ? C15 C20 H9 120.1 . . ? C19 C20 H9 120.1 . . ? 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 C9 P1 N1 C1 -131.6(2) . . . . ? C15 P1 N1 C1 119.4(2) . . . . ? Se1 P1 N1 C1 -7.2(3) . . . . ? P1 N1 C1 C2 87.7(4) . . . . ? P1 N1 C1 C6 -94.4(3) . . . . ? C6 C1 C2 C3 -2.0(6) . . . . ? N1 C1 C2 C3 175.8(3) . . . . ? C6 C1 C2 C8 -179.8(3) . . . . ? N1 C1 C2 C8 -1.9(6) . . . . ? C1 C2 C3 C4 1.5(6) . . . . ? C8 C2 C3 C4 179.3(4) . . . . ? C2 C3 C4 C5 0.2(6) . . . . ? C3 C4 C5 C6 -1.6(6) . . . . ? C4 C5 C6 C1 1.2(5) . . . . ? C4 C5 C6 C7 -177.8(3) . . . . ? C2 C1 C6 C5 0.7(5) . . . . ? N1 C1 C6 C5 -177.2(3) . . . . ? C2 C1 C6 C7 179.7(3) . . . . ? N1 C1 C6 C7 1.8(5) . . . . ? N1 P1 C9 C10 -2.4(3) . . . . ? C15 P1 C9 C10 110.9(3) . . . . ? Se1 P1 C9 C10 -125.0(2) . . . . ? N1 P1 C9 C14 178.5(2) . . . . ? C15 P1 C9 C14 -68.2(3) . . . . ? Se1 P1 C9 C14 55.9(2) . . . . ? C14 C9 C10 C11 -1.3(5) . . . . ? P1 C9 C10 C11 179.7(2) . . . . ? C9 C10 C11 C12 0.1(5) . . . . ? C10 C11 C12 C13 0.7(5) . . . . ? C11 C12 C13 C14 -0.3(5) . . . . ? C12 C13 C14 C9 -0.9(5) . . . . ? C10 C9 C14 C13 1.7(5) . . . . ? P1 C9 C14 C13 -179.2(2) . . . . ? N1 P1 C15 C20 -142.4(3) . . . . ? C9 P1 C15 C20 106.2(3) . . . . ? Se1 P1 C15 C20 -17.6(3) . . . . ? N1 P1 C15 C16 41.9(3) . . . . ? C9 P1 C15 C16 -69.5(3) . . . . ? Se1 P1 C15 C16 166.7(2) . . . . ? C20 C15 C16 C17 0.7(5) . . . . ? P1 C15 C16 C17 176.5(3) . . . . ? C15 C16 C17 C18 0.7(5) . . . . ? C16 C17 C18 C19 -1.5(6) . . . . ? C17 C18 C19 C20 0.9(6) . . . . ? C16 C15 C20 C19 -1.3(5) . . . . ? P1 C15 C20 C19 -177.0(3) . . . . ? C18 C19 C20 C15 0.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 70.80 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.579 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.063