Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2003 data_global _audit_creation_method SHELXL-97 _journal_coden_Cambridge 222 _publ_contact_author_name 'Paul J. Dyson' _publ_contact_author_address ; Institut de Chimie Moléculaire et Biologique École Polytechnique Fédérale de Lausanne 1015 Lausanne Switzerland ; _publ_contact_author_email paul.dyson@epfl.ch _publ_contact_author_fax '+41 21 693 9885' _publ_contact_author_phone '+41 21 693 9854' _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Influence of the functional group on the synthesis of aminophosphines, diphosphinoamines and iminobiphosphines. ; loop_ _publ_author_name _publ_author_address 'Fei, Zhaofu' ; Institut de Chimie Moléculaire et Biologique École Polytechnique Fédérale de Lausanne 1015 Lausanne Switzerland ; 'Scopelliti, Rosario' ; Institut de Chimie Moléculaire et Biologique École Polytechnique Fédérale de Lausanne 1015 Lausanne Switzerland ; 'Dyson, Paul J.' ; Institut de Chimie Moléculaire et Biologique École Polytechnique Fédérale de Lausanne 1015 Lausanne Switzerland ; data_3b _database_code_CSD 207371 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H24 N2 P2' _chemical_formula_weight 486.46 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' 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 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 11.397(4) _cell_length_b 11.702(4) _cell_length_c 18.829(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.048(19) _cell_angle_gamma 90.00 _cell_volume 2510.7(12) _cell_formula_units_Z 4 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 2462 _cell_measurement_theta_min 1.78825 _cell_measurement_theta_max 21.13005 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.196 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; (See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166) ; _exptl_absorpt_correction_T_min 0.2490 _exptl_absorpt_correction_T_max 0.7060 _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'marresearch mar345 IPDS' _diffrn_measurement_method '60 images with deltaphi = 3 deg. and exp. time = 180 sec.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13933 _diffrn_reflns_av_R_equivalents 0.0668 _diffrn_reflns_av_sigmaI/netI 0.0498 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4318 _reflns_number_gt 3263 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'marresearch, mar345' _computing_cell_refinement 'Oxford Diffraction CrysAlis RED' _computing_data_reduction 'Oxford Diffraction CrysAlis RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1301P)^2^+0.7289P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.001(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4318 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0842 _refine_ls_R_factor_gt 0.0708 _refine_ls_wR_factor_ref 0.2181 _refine_ls_wR_factor_gt 0.2009 _refine_ls_goodness_of_fit_ref 1.165 _refine_ls_restrained_S_all 1.165 _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 0.28559(7) 0.31564(7) 0.05059(4) 0.0439(3) Uani 1 1 d . . . P2 P 0.23950(8) 0.17084(7) 0.17227(4) 0.0449(3) Uani 1 1 d . . . N1 N 0.2600(2) 0.1790(2) 0.08200(13) 0.0428(6) Uani 1 1 d . . . N2 N 0.2366(3) -0.2907(3) -0.13117(16) 0.0605(8) Uani 1 1 d . . . C1 C 0.2556(3) 0.0805(3) 0.03666(16) 0.0422(7) Uani 1 1 d . . . C2 C 0.3521(3) 0.0072(3) 0.03252(17) 0.0452(7) Uani 1 1 d . . . H2 H 0.4215 0.0232 0.0595 0.054 Uiso 1 1 calc R . . C3 C 0.3473(3) -0.0882(3) -0.01042(17) 0.0458(7) Uani 1 1 d . . . H3 H 0.4133 -0.1375 -0.0131 0.055 Uiso 1 1 calc R . . C4 C 0.2461(3) -0.1121(3) -0.04978(15) 0.0433(7) Uani 1 1 d . . . C5 C 0.1493(3) -0.0401(3) -0.04585(16) 0.0459(7) Uani 1 1 d . . . H5 H 0.0800 -0.0566 -0.0727 0.055 Uiso 1 1 calc R . . C6 C 0.1542(3) 0.0550(3) -0.00302(16) 0.0450(7) Uani 1 1 d . . . H6 H 0.0878 0.1039 -0.0004 0.054 Uiso 1 1 calc R . . C7 C 0.2407(3) -0.2115(3) -0.09499(18) 0.0487(8) Uani 1 1 d . . . C8 C 0.1606(3) 0.3449(3) -0.00935(16) 0.0465(7) Uani 1 1 d . . . C9 C 0.0478(3) 0.3215(3) 0.01318(18) 0.0491(8) Uani 1 1 d . . . H9 H 0.0371 0.2809 0.0563 0.059 Uiso 1 1 calc R . . C10 C -0.0495(3) 0.3567(3) -0.02648(19) 0.0534(8) Uani 1 1 d . . . H10 H -0.1261 0.3388 -0.0109 0.064 Uiso 1 1 calc R . . C11 C -0.0351(3) 0.4179(3) -0.08867(18) 0.0516(8) Uani 1 1 d . . . H11 H -0.1017 0.4417 -0.1158 0.062 Uiso 1 1 calc R . . C12 C 0.0762(3) 0.4441(3) -0.11107(17) 0.0515(8) Uani 1 1 d . . . H12 H 0.0863 0.4872 -0.1533 0.062 Uiso 1 1 calc R . . C13 C 0.1733(3) 0.4074(3) -0.07192(17) 0.0479(7) Uani 1 1 d . . . H13 H 0.2498 0.4250 -0.0879 0.058 Uiso 1 1 calc R . . C14 C 0.4050(3) 0.2993(3) -0.01265(17) 0.0455(7) Uani 1 1 d . . . C15 C 0.5077(3) 0.3601(3) 0.00337(19) 0.0501(8) Uani 1 1 d . . . H15 H 0.5142 0.4014 0.0467 0.060 Uiso 1 1 calc R . . C16 C 0.6007(3) 0.3606(3) -0.0437(2) 0.0590(9) Uani 1 1 d . . . H16 H 0.6698 0.4029 -0.0325 0.071 Uiso 1 1 calc R . . C17 C 0.5925(3) 0.2999(3) -0.1064(2) 0.0614(10) Uani 1 1 d . . . H17 H 0.6560 0.2999 -0.1384 0.074 Uiso 1 1 calc R . . C18 C 0.4913(3) 0.2388(3) -0.12259(19) 0.0597(9) Uani 1 1 d . . . H18 H 0.4858 0.1970 -0.1658 0.072 Uiso 1 1 calc R . . C19 C 0.3982(3) 0.2382(3) -0.07641(17) 0.0517(8) Uani 1 1 d . . . H19 H 0.3293 0.1959 -0.0881 0.062 Uiso 1 1 calc R . . C20 C 0.3635(3) 0.0851(3) 0.20582(16) 0.0467(7) Uani 1 1 d . . . C21 C 0.4772(3) 0.1170(3) 0.18659(17) 0.0508(8) Uani 1 1 d . . . H21 H 0.4873 0.1754 0.1522 0.061 Uiso 1 1 calc R . . C22 C 0.5746(3) 0.0649(4) 0.21674(19) 0.0588(9) Uani 1 1 d . . . H22 H 0.6508 0.0872 0.2025 0.071 Uiso 1 1 calc R . . C23 C 0.5623(3) -0.0201(3) 0.26772(18) 0.0575(9) Uani 1 1 d . . . H23 H 0.6292 -0.0562 0.2884 0.069 Uiso 1 1 calc R . . C24 C 0.4504(3) -0.0507(3) 0.28760(17) 0.0539(8) Uani 1 1 d . . . H24 H 0.4409 -0.1084 0.3225 0.065 Uiso 1 1 calc R . . C25 C 0.3524(3) 0.0010(3) 0.25780(16) 0.0479(8) Uani 1 1 d . . . H25 H 0.2765 -0.0209 0.2729 0.057 Uiso 1 1 calc R . . C26 C 0.1163(3) 0.0715(3) 0.18058(16) 0.0467(7) Uani 1 1 d . . . C27 C 0.1177(3) -0.0451(3) 0.16327(17) 0.0514(8) Uani 1 1 d . . . H27 H 0.1857 -0.0773 0.1427 0.062 Uiso 1 1 calc R . . C28 C 0.0207(3) -0.1145(3) 0.1759(2) 0.0599(9) Uani 1 1 d . . . H28 H 0.0223 -0.1932 0.1634 0.072 Uiso 1 1 calc R . . C29 C -0.0780(3) -0.0681(4) 0.20672(19) 0.0621(10) Uani 1 1 d . . . H29 H -0.1435 -0.1154 0.2164 0.075 Uiso 1 1 calc R . . C30 C -0.0813(3) 0.0461(4) 0.22327(17) 0.0588(9) Uani 1 1 d . . . H30 H -0.1496 0.0778 0.2438 0.071 Uiso 1 1 calc R . . C31 C 0.0149(3) 0.1159(3) 0.21016(16) 0.0510(8) Uani 1 1 d . . . H31 H 0.0113 0.1948 0.2216 0.061 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 0.0475(5) 0.0410(5) 0.0434(5) 0.0004(3) 0.0011(4) 0.0013(3) P2 0.0483(5) 0.0454(5) 0.0409(5) -0.0007(3) -0.0004(4) 0.0014(3) N1 0.0480(15) 0.0369(14) 0.0433(14) -0.0026(10) -0.0025(11) 0.0022(11) N2 0.065(2) 0.0554(19) 0.0613(18) -0.0099(14) 0.0067(15) -0.0032(15) C1 0.0407(16) 0.0428(17) 0.0431(15) 0.0021(12) 0.0035(12) 0.0007(13) C2 0.0398(16) 0.0464(17) 0.0492(16) 0.0037(13) -0.0021(13) 0.0003(13) C3 0.0468(17) 0.0410(17) 0.0498(17) 0.0028(12) 0.0043(13) -0.0003(13) C4 0.0440(16) 0.0445(17) 0.0413(15) -0.0013(12) 0.0014(12) -0.0016(13) C5 0.0434(17) 0.0505(19) 0.0439(16) -0.0003(13) -0.0002(13) -0.0005(13) C6 0.0411(16) 0.0475(18) 0.0466(16) 0.0005(13) 0.0021(13) 0.0035(13) C7 0.0474(18) 0.0491(19) 0.0500(17) -0.0014(14) 0.0074(14) -0.0028(14) C8 0.0507(19) 0.0431(17) 0.0456(16) -0.0017(13) 0.0036(14) 0.0028(14) C9 0.055(2) 0.0441(18) 0.0484(17) 0.0051(13) 0.0060(14) 0.0073(14) C10 0.051(2) 0.0500(19) 0.0592(19) -0.0012(15) 0.0043(15) 0.0054(15) C11 0.053(2) 0.0491(19) 0.0526(18) -0.0008(14) -0.0061(15) 0.0055(15) C12 0.058(2) 0.055(2) 0.0422(16) 0.0058(13) 0.0011(14) 0.0050(15) C13 0.0483(18) 0.0450(18) 0.0506(17) 0.0007(13) 0.0034(14) 0.0025(14) C14 0.0497(18) 0.0398(17) 0.0470(16) 0.0018(12) -0.0017(13) 0.0027(13) C15 0.0501(18) 0.0425(18) 0.0575(18) 0.0069(14) -0.0030(14) 0.0043(14) C16 0.049(2) 0.050(2) 0.078(2) 0.0143(17) 0.0071(17) 0.0025(15) C17 0.056(2) 0.060(2) 0.069(2) 0.0145(17) 0.0137(18) 0.0059(17) C18 0.069(2) 0.060(2) 0.0512(18) 0.0053(15) 0.0131(16) 0.0166(18) C19 0.056(2) 0.0475(19) 0.0516(17) 0.0026(14) 0.0014(15) 0.0017(15) C20 0.0476(18) 0.0499(19) 0.0425(16) -0.0007(13) -0.0013(13) -0.0035(14) C21 0.055(2) 0.055(2) 0.0422(16) 0.0062(14) -0.0036(14) -0.0075(15) C22 0.050(2) 0.072(2) 0.0538(19) 0.0067(17) -0.0062(15) -0.0088(17) C23 0.054(2) 0.068(2) 0.0502(18) 0.0028(16) -0.0077(15) 0.0059(17) C24 0.059(2) 0.056(2) 0.0461(17) 0.0071(14) -0.0004(15) -0.0003(16) C25 0.0486(18) 0.0534(19) 0.0418(15) 0.0029(13) 0.0022(13) -0.0005(14) C26 0.0498(18) 0.0504(19) 0.0398(15) 0.0041(13) -0.0031(13) 0.0021(14) C27 0.055(2) 0.0520(19) 0.0468(17) 0.0083(14) 0.0020(14) 0.0008(15) C28 0.061(2) 0.057(2) 0.060(2) 0.0115(16) -0.0048(17) -0.0113(17) C29 0.053(2) 0.080(3) 0.054(2) 0.0129(17) -0.0059(16) -0.0138(19) C30 0.0420(19) 0.089(3) 0.0448(17) 0.0010(17) -0.0027(14) -0.0003(17) C31 0.0488(19) 0.063(2) 0.0406(16) -0.0012(14) -0.0037(13) 0.0053(15) _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 N1 1.732(3) . ? P1 C8 1.834(4) . ? P1 C14 1.834(3) . ? P2 N1 1.723(3) . ? P2 C26 1.832(3) . ? P2 C20 1.835(3) . ? N1 C1 1.434(4) . ? N2 C7 1.151(5) . ? C1 C6 1.397(5) . ? C1 C2 1.399(4) . ? C2 C3 1.379(5) . ? C2 H2 0.9500 . ? C3 C4 1.389(5) . ? C3 H3 0.9500 . ? C4 C5 1.391(5) . ? C4 C7 1.441(5) . ? C5 C6 1.375(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C8 C9 1.388(5) . ? C8 C13 1.396(5) . ? C9 C10 1.388(5) . ? C9 H9 0.9500 . ? C10 C11 1.385(5) . ? C10 H10 0.9500 . ? C11 C12 1.378(5) . ? C11 H11 0.9500 . ? C12 C13 1.387(5) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.399(5) . ? C14 C19 1.399(5) . ? C15 C16 1.393(5) . ? C15 H15 0.9500 . ? C16 C17 1.380(6) . ? C16 H16 0.9500 . ? C17 C18 1.386(6) . ? C17 H17 0.9500 . ? C18 C19 1.385(5) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C25 1.395(4) . ? C20 C21 1.402(5) . ? C21 C22 1.380(5) . ? C21 H21 0.9500 . ? C22 C23 1.391(5) . ? C22 H22 0.9500 . ? C23 C24 1.382(5) . ? C23 H23 0.9500 . ? C24 C25 1.381(5) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C31 1.392(5) . ? C26 C27 1.404(5) . ? C27 C28 1.395(5) . ? C27 H27 0.9500 . ? C28 C29 1.387(6) . ? C28 H28 0.9500 . ? C29 C30 1.373(6) . ? C29 H29 0.9500 . ? C30 C31 1.392(5) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? 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 C8 104.42(14) . . ? N1 P1 C14 104.90(14) . . ? C8 P1 C14 101.36(14) . . ? N1 P2 C26 103.72(14) . . ? N1 P2 C20 104.62(13) . . ? C26 P2 C20 102.14(15) . . ? C1 N1 P2 122.6(2) . . ? C1 N1 P1 122.9(2) . . ? P2 N1 P1 114.49(14) . . ? C6 C1 C2 118.9(3) . . ? C6 C1 N1 120.6(3) . . ? C2 C1 N1 120.5(3) . . ? C3 C2 C1 120.4(3) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 120.0(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 120.1(3) . . ? C3 C4 C7 120.2(3) . . ? C5 C4 C7 119.7(3) . . ? C6 C5 C4 119.9(3) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C1 120.7(3) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? N2 C7 C4 179.9(5) . . ? C9 C8 C13 118.2(3) . . ? C9 C8 P1 119.2(2) . . ? C13 C8 P1 121.7(3) . . ? C10 C9 C8 120.8(3) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C11 C10 C9 120.2(3) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C12 C11 C10 119.8(3) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C13 119.9(3) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C13 C8 121.1(3) . . ? C12 C13 H13 119.5 . . ? C8 C13 H13 119.5 . . ? C15 C14 C19 118.6(3) . . ? C15 C14 P1 115.8(2) . . ? C19 C14 P1 125.5(3) . . ? C16 C15 C14 120.6(3) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C17 C16 C15 120.1(4) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 119.8(3) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C19 C18 C17 120.6(4) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C18 C19 C14 120.4(3) . . ? C18 C19 H19 119.8 . . ? C14 C19 H19 119.8 . . ? C25 C20 C21 117.7(3) . . ? C25 C20 P2 123.2(2) . . ? C21 C20 P2 118.4(2) . . ? C22 C21 C20 121.1(3) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C21 C22 C23 120.6(3) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C24 C23 C22 118.5(3) . . ? C24 C23 H23 120.7 . . ? C22 C23 H23 120.7 . . ? C25 C24 C23 121.3(3) . . ? C25 C24 H24 119.3 . . ? C23 C24 H24 119.3 . . ? C24 C25 C20 120.7(3) . . ? C24 C25 H25 119.6 . . ? C20 C25 H25 119.6 . . ? C31 C26 C27 117.9(3) . . ? C31 C26 P2 116.2(3) . . ? C27 C26 P2 125.8(3) . . ? C28 C27 C26 120.9(3) . . ? C28 C27 H27 119.5 . . ? C26 C27 H27 119.5 . . ? C29 C28 C27 119.6(4) . . ? C29 C28 H28 120.2 . . ? C27 C28 H28 120.2 . . ? C30 C29 C28 120.1(3) . . ? C30 C29 H29 119.9 . . ? C28 C29 H29 119.9 . . ? C29 C30 C31 120.4(4) . . ? C29 C30 H30 119.8 . . ? C31 C30 H30 119.8 . . ? C26 C31 C30 121.0(4) . . ? C26 C31 H31 119.5 . . ? C30 C31 H31 119.5 . . ? 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 C26 P2 N1 C1 -42.3(3) . . . . ? C20 P2 N1 C1 64.4(3) . . . . ? C26 P2 N1 P1 137.42(17) . . . . ? C20 P2 N1 P1 -115.87(17) . . . . ? C8 P1 N1 C1 63.0(3) . . . . ? C14 P1 N1 C1 -43.2(3) . . . . ? C8 P1 N1 P2 -116.74(17) . . . . ? C14 P1 N1 P2 137.06(17) . . . . ? P2 N1 C1 C6 99.1(3) . . . . ? P1 N1 C1 C6 -80.6(3) . . . . ? P2 N1 C1 C2 -79.6(3) . . . . ? P1 N1 C1 C2 100.7(3) . . . . ? C6 C1 C2 C3 0.5(5) . . . . ? N1 C1 C2 C3 179.2(3) . . . . ? C1 C2 C3 C4 -0.2(5) . . . . ? C2 C3 C4 C5 -0.1(5) . . . . ? C2 C3 C4 C7 179.7(3) . . . . ? C3 C4 C5 C6 0.1(5) . . . . ? C7 C4 C5 C6 -179.7(3) . . . . ? C4 C5 C6 C1 0.2(5) . . . . ? C2 C1 C6 C5 -0.5(5) . . . . ? N1 C1 C6 C5 -179.2(3) . . . . ? C3 C4 C7 N2 -78(100) . . . . ? C5 C4 C7 N2 102(100) . . . . ? N1 P1 C8 C9 47.5(3) . . . . ? C14 P1 C8 C9 156.3(3) . . . . ? N1 P1 C8 C13 -143.4(3) . . . . ? C14 P1 C8 C13 -34.6(3) . . . . ? C13 C8 C9 C10 1.6(5) . . . . ? P1 C8 C9 C10 171.2(3) . . . . ? C8 C9 C10 C11 -1.2(5) . . . . ? C9 C10 C11 C12 -0.2(5) . . . . ? C10 C11 C12 C13 1.1(5) . . . . ? C11 C12 C13 C8 -0.7(5) . . . . ? C9 C8 C13 C12 -0.7(5) . . . . ? P1 C8 C13 C12 -169.9(3) . . . . ? N1 P1 C14 C15 -119.6(3) . . . . ? C8 P1 C14 C15 132.0(3) . . . . ? N1 P1 C14 C19 64.7(3) . . . . ? C8 P1 C14 C19 -43.7(3) . . . . ? C19 C14 C15 C16 0.7(5) . . . . ? P1 C14 C15 C16 -175.2(3) . . . . ? C14 C15 C16 C17 -0.7(5) . . . . ? C15 C16 C17 C18 0.3(6) . . . . ? C16 C17 C18 C19 0.0(6) . . . . ? C17 C18 C19 C14 0.0(5) . . . . ? C15 C14 C19 C18 -0.4(5) . . . . ? P1 C14 C19 C18 175.1(3) . . . . ? N1 P2 C20 C25 -138.7(3) . . . . ? C26 P2 C20 C25 -30.9(3) . . . . ? N1 P2 C20 C21 51.4(3) . . . . ? C26 P2 C20 C21 159.2(3) . . . . ? C25 C20 C21 C22 1.6(5) . . . . ? P2 C20 C21 C22 172.1(3) . . . . ? C20 C21 C22 C23 -0.7(6) . . . . ? C21 C22 C23 C24 -0.2(6) . . . . ? C22 C23 C24 C25 0.2(6) . . . . ? C23 C24 C25 C20 0.8(5) . . . . ? C21 C20 C25 C24 -1.7(5) . . . . ? P2 C20 C25 C24 -171.7(3) . . . . ? N1 P2 C26 C31 -117.2(2) . . . . ? C20 P2 C26 C31 134.3(2) . . . . ? N1 P2 C26 C27 66.3(3) . . . . ? C20 P2 C26 C27 -42.3(3) . . . . ? C31 C26 C27 C28 -0.5(5) . . . . ? P2 C26 C27 C28 176.0(3) . . . . ? C26 C27 C28 C29 -0.8(5) . . . . ? C27 C28 C29 C30 1.5(5) . . . . ? C28 C29 C30 C31 -0.9(5) . . . . ? C27 C26 C31 C30 1.1(5) . . . . ? P2 C26 C31 C30 -175.7(2) . . . . ? C29 C30 C31 C26 -0.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.501 _refine_diff_density_min -0.434 _refine_diff_density_rms 0.083 data_3c _database_code_CSD 207372 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H24 N2 P2' _chemical_formula_weight 486.46 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' 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 Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 16.8591(16) _cell_length_b 17.3905(12) _cell_length_c 8.7547(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2566.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 3565 _cell_measurement_theta_min 2.445 _cell_measurement_theta_max 23.8991 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.192 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(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 'Oxford Diffraction KM4/Sapphire CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14985 _diffrn_reflns_av_R_equivalents 0.0770 _diffrn_reflns_av_sigmaI/netI 0.0467 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2343 _reflns_number_gt 1999 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Oxford Diffraction CrysAlis CCD' _computing_cell_refinement 'Oxford Diffraction CrysAlis RED' _computing_data_reduction 'Oxford Diffraction CrysAlis RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0259P)^2^+4.6775P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2343 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0962 _refine_ls_R_factor_gt 0.0784 _refine_ls_wR_factor_ref 0.1488 _refine_ls_wR_factor_gt 0.1419 _refine_ls_goodness_of_fit_ref 1.292 _refine_ls_restrained_S_all 1.292 _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 0.18801(6) -0.16646(5) 0.15427(10) 0.0257(3) Uani 1 1 d . . . N1 N 0.2085(3) -0.2500 0.0510(4) 0.0240(10) Uani 1 2 d S . . N2 N -0.0005(4) -0.2500 -0.4913(6) 0.0498(14) Uani 1 2 d S . . C1 C 0.2072(3) -0.2500 -0.1144(5) 0.0228(12) Uani 1 2 d S . . C2 C 0.1355(3) -0.2500 -0.1922(6) 0.0262(12) Uani 1 2 d S . . H2 H 0.0870 -0.2500 -0.1369 0.031 Uiso 1 2 calc SR . . C3 C 0.1345(3) -0.2500 -0.3519(6) 0.0278(12) Uani 1 2 d S . . C4 C 0.2051(4) -0.2500 -0.4345(6) 0.0351(14) Uani 1 2 d S . . H4 H 0.2043 -0.2500 -0.5430 0.042 Uiso 1 2 calc SR . . C5 C 0.2764(4) -0.2500 -0.3569(6) 0.0337(13) Uani 1 2 d S . . H5 H 0.3248 -0.2500 -0.4123 0.040 Uiso 1 2 calc SR . . C6 C 0.2776(3) -0.2500 -0.1973(6) 0.0286(13) Uani 1 2 d S . . H6 H 0.3269 -0.2500 -0.1449 0.034 Uiso 1 2 calc SR . . C7 C 0.0588(4) -0.2500 -0.4292(6) 0.0367(14) Uani 1 2 d S . . C8 C 0.2631(2) -0.0996(2) 0.0848(4) 0.0282(9) Uani 1 1 d . . . C9 C 0.3404(2) -0.1229(2) 0.0546(4) 0.0333(10) Uani 1 1 d . . . H9 H 0.3541 -0.1755 0.0673 0.040 Uiso 1 1 calc R . . C10 C 0.3976(3) -0.0718(3) 0.0068(5) 0.0491(12) Uani 1 1 d . . . H10 H 0.4495 -0.0898 -0.0156 0.059 Uiso 1 1 calc R . . C11 C 0.3799(3) 0.0054(3) -0.0088(6) 0.0541(13) Uani 1 1 d . . . H11 H 0.4190 0.0406 -0.0440 0.065 Uiso 1 1 calc R . . C12 C 0.3052(3) 0.0306(3) 0.0272(6) 0.0562(14) Uani 1 1 d . . . H12 H 0.2929 0.0837 0.0193 0.067 Uiso 1 1 calc R . . C13 C 0.2476(3) -0.0207(2) 0.0748(5) 0.0430(11) Uani 1 1 d . . . H13 H 0.1965 -0.0020 0.1014 0.052 Uiso 1 1 calc R . . C14 C 0.0978(2) -0.1291(2) 0.0632(4) 0.0270(9) Uani 1 1 d . . . C15 C 0.0263(2) -0.1481(2) 0.1348(5) 0.0351(10) Uani 1 1 d . . . H15 H 0.0270 -0.1718 0.2326 0.042 Uiso 1 1 calc R . . C16 C -0.0462(3) -0.1327(3) 0.0639(6) 0.0456(12) Uani 1 1 d . . . H16 H -0.0945 -0.1464 0.1127 0.055 Uiso 1 1 calc R . . C17 C -0.0472(3) -0.0975(3) -0.0779(6) 0.0454(12) Uani 1 1 d . . . H17 H -0.0963 -0.0884 -0.1281 0.054 Uiso 1 1 calc R . . C18 C 0.0224(3) -0.0758(2) -0.1459(5) 0.0395(10) Uani 1 1 d . . . H18 H 0.0210 -0.0496 -0.2410 0.047 Uiso 1 1 calc R . . C19 C 0.0944(2) -0.0916(2) -0.0779(4) 0.0315(9) Uani 1 1 d . . . H19 H 0.1422 -0.0768 -0.1275 0.038 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 0.0367(5) 0.0226(5) 0.0177(4) -0.0011(4) -0.0007(4) 0.0003(4) N1 0.036(3) 0.021(2) 0.015(2) 0.000 -0.0013(18) 0.000 N2 0.063(4) 0.049(3) 0.038(3) 0.000 -0.017(3) 0.000 C1 0.036(3) 0.016(2) 0.017(2) 0.000 -0.003(2) 0.000 C2 0.038(3) 0.018(3) 0.022(3) 0.000 0.000(2) 0.000 C3 0.046(3) 0.017(3) 0.021(3) 0.000 -0.007(3) 0.000 C4 0.064(4) 0.024(3) 0.017(3) 0.000 0.003(3) 0.000 C5 0.046(4) 0.032(3) 0.023(3) 0.000 0.007(3) 0.000 C6 0.038(3) 0.026(3) 0.023(3) 0.000 -0.003(2) 0.000 C7 0.056(4) 0.029(3) 0.025(3) 0.000 -0.014(3) 0.000 C8 0.038(2) 0.024(2) 0.0228(18) -0.0031(17) -0.0051(17) -0.0006(17) C9 0.038(2) 0.028(2) 0.033(2) -0.0040(19) -0.0054(18) -0.0035(18) C10 0.041(3) 0.054(3) 0.052(3) -0.009(2) -0.002(2) -0.009(2) C11 0.052(3) 0.055(3) 0.056(3) 0.008(3) -0.010(2) -0.026(3) C12 0.065(4) 0.025(2) 0.078(4) 0.008(2) -0.021(3) -0.012(2) C13 0.042(3) 0.026(2) 0.061(3) -0.002(2) -0.005(2) 0.001(2) C14 0.034(2) 0.022(2) 0.0250(19) -0.0061(16) 0.0018(17) 0.0001(17) C15 0.044(2) 0.031(2) 0.030(2) -0.0023(18) 0.0069(19) 0.0000(18) C16 0.034(2) 0.048(3) 0.056(3) -0.009(2) 0.004(2) 0.004(2) C17 0.040(3) 0.040(3) 0.056(3) -0.014(2) -0.010(2) 0.013(2) C18 0.053(3) 0.029(2) 0.037(2) -0.002(2) -0.010(2) 0.008(2) C19 0.042(2) 0.022(2) 0.031(2) -0.0021(17) -0.0023(18) 0.0010(18) _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 N1 1.746(2) . ? P1 C8 1.823(4) . ? P1 C14 1.836(4) . ? N1 C1 1.449(6) . ? N1 P1 1.746(2) 7 ? N2 C7 1.138(8) . ? C1 C2 1.387(7) . ? C1 C6 1.391(7) . ? C2 C3 1.398(7) . ? C2 H2 0.9500 . ? C3 C4 1.394(8) . ? C3 C7 1.444(8) . ? C4 C5 1.380(8) . ? C4 H4 0.9500 . ? C5 C6 1.397(7) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C8 C9 1.390(5) . ? C8 C13 1.400(5) . ? C9 C10 1.377(6) . ? C9 H9 0.9500 . ? C10 C11 1.383(7) . ? C10 H10 0.9500 . ? C11 C12 1.370(7) . ? C11 H11 0.9500 . ? C12 C13 1.383(6) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.398(5) . ? C14 C19 1.399(5) . ? C15 C16 1.396(6) . ? C15 H15 0.9500 . ? C16 C17 1.384(7) . ? C16 H16 0.9500 . ? C17 C18 1.369(6) . ? C17 H17 0.9500 . ? C18 C19 1.380(6) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? 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 C8 102.72(18) . . ? N1 P1 C14 103.51(18) . . ? C8 P1 C14 101.83(17) . . ? C1 N1 P1 120.97(14) . 7 ? C1 N1 P1 120.97(14) . . ? P1 N1 P1 112.7(2) 7 . ? C2 C1 C6 119.2(4) . . ? C2 C1 N1 120.3(5) . . ? C6 C1 N1 120.5(5) . . ? C1 C2 C3 120.1(5) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 120.5(5) . . ? C4 C3 C7 120.8(5) . . ? C2 C3 C7 118.7(5) . . ? C5 C4 C3 119.2(5) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 120.3(5) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 120.6(5) . . ? C1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? N2 C7 C3 179.4(7) . . ? C9 C8 C13 116.7(4) . . ? C9 C8 P1 121.9(3) . . ? C13 C8 P1 121.1(3) . . ? C10 C9 C8 121.8(4) . . ? C10 C9 H9 119.1 . . ? C8 C9 H9 119.1 . . ? C9 C10 C11 120.4(5) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 119.0(4) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C11 C12 C13 120.6(4) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C8 121.4(4) . . ? C12 C13 H13 119.3 . . ? C8 C13 H13 119.3 . . ? C15 C14 C19 118.1(4) . . ? C15 C14 P1 115.9(3) . . ? C19 C14 P1 125.6(3) . . ? C16 C15 C14 120.6(4) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C17 C16 C15 119.7(4) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C18 C17 C16 120.1(4) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C18 C19 120.8(4) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? C18 C19 C14 120.6(4) . . ? C18 C19 H19 119.7 . . ? C14 C19 H19 119.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 P1 N1 C1 -58.6(4) . . . . ? C14 P1 N1 C1 47.1(4) . . . . ? C8 P1 N1 P1 147.1(2) . . . 7 ? C14 P1 N1 P1 -107.2(2) . . . 7 ? P1 N1 C1 C2 76.1(3) 7 . . . ? P1 N1 C1 C2 -76.1(3) . . . . ? P1 N1 C1 C6 -103.9(3) 7 . . . ? P1 N1 C1 C6 103.9(3) . . . . ? C6 C1 C2 C3 0.0 . . . . ? N1 C1 C2 C3 180.0 . . . . ? C1 C2 C3 C4 0.0 . . . . ? C1 C2 C3 C7 180.0 . . . . ? C2 C3 C4 C5 0.0 . . . . ? C7 C3 C4 C5 180.0 . . . . ? C3 C4 C5 C6 0.0 . . . . ? C2 C1 C6 C5 0.0 . . . . ? N1 C1 C6 C5 180.0 . . . . ? C4 C5 C6 C1 0.0 . . . . ? C4 C3 C7 N2 0.00(9) . . . . ? C2 C3 C7 N2 180.00(9) . . . . ? N1 P1 C8 C9 -39.0(4) . . . . ? C14 P1 C8 C9 -146.0(3) . . . . ? N1 P1 C8 C13 147.8(3) . . . . ? C14 P1 C8 C13 40.9(4) . . . . ? C13 C8 C9 C10 -4.5(6) . . . . ? P1 C8 C9 C10 -177.9(3) . . . . ? C8 C9 C10 C11 1.7(7) . . . . ? C9 C10 C11 C12 1.4(7) . . . . ? C10 C11 C12 C13 -1.6(8) . . . . ? C11 C12 C13 C8 -1.4(8) . . . . ? C9 C8 C13 C12 4.3(6) . . . . ? P1 C8 C13 C12 177.8(4) . . . . ? N1 P1 C14 C15 96.8(3) . . . . ? C8 P1 C14 C15 -156.8(3) . . . . ? N1 P1 C14 C19 -75.6(3) . . . . ? C8 P1 C14 C19 30.8(4) . . . . ? C19 C14 C15 C16 2.6(5) . . . . ? P1 C14 C15 C16 -170.5(3) . . . . ? C14 C15 C16 C17 -0.7(6) . . . . ? C15 C16 C17 C18 -2.0(6) . . . . ? C16 C17 C18 C19 2.9(6) . . . . ? C17 C18 C19 C14 -1.0(6) . . . . ? C15 C14 C19 C18 -1.8(5) . . . . ? P1 C14 C19 C18 170.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.332 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.064 data_4b _database_code_CSD 207373 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H24 N2 P2' _chemical_formula_weight 486.46 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' 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 Cc 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 15.778(3) _cell_length_b 11.6783(16) _cell_length_c 15.070(2) _cell_angle_alpha 90.00 _cell_angle_beta 112.375(15) _cell_angle_gamma 90.00 _cell_volume 2567.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 2177 _cell_measurement_theta_min 2.38915 _cell_measurement_theta_max 21.27605 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.192 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; (See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166) ; _exptl_absorpt_correction_T_min 0.2600 _exptl_absorpt_correction_T_max 0.7140 _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(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 'Oxford Diffraction KM4/Sapphire CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7264 _diffrn_reflns_av_R_equivalents 0.0690 _diffrn_reflns_av_sigmaI/netI 0.0695 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.78 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3951 _reflns_number_gt 2905 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Oxford Diffraction CrysAlis CCD' _computing_cell_refinement 'Oxford Diffraction CrysAlis RED' _computing_data_reduction 'Oxford Diffraction CrysAlis RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1146P)^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 mixed _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 0.29(16) _refine_ls_number_reflns 3951 _refine_ls_number_parameters 317 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0810 _refine_ls_R_factor_gt 0.0663 _refine_ls_wR_factor_ref 0.1787 _refine_ls_wR_factor_gt 0.1643 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.973 _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 -0.03388(8) 0.22835(12) 0.30746(8) 0.0433(4) Uani 1 1 d . . . P2 P 0.10170(9) 0.24918(13) 0.29290(9) 0.0474(4) Uani 1 1 d . . . N1 N -0.0909(3) 0.1146(4) 0.2773(3) 0.0454(11) Uani 1 1 d . . . N2 N -0.3470(4) -0.1183(5) -0.1542(4) 0.0787(17) Uani 1 1 d . . . C1 C -0.1413(3) 0.0691(5) 0.1880(4) 0.0460(12) Uani 1 1 d . . . C2 C -0.1486(3) 0.1196(5) 0.1006(3) 0.0445(12) Uani 1 1 d . . . H2 H -0.1177 0.1894 0.1004 0.053 Uiso 1 1 calc R . . C3 C -0.2013(4) 0.0668(5) 0.0142(4) 0.0500(13) Uani 1 1 d . . . H3 H -0.2053 0.1013 -0.0443 0.060 Uiso 1 1 calc R . . C4 C -0.2475(4) -0.0333(5) 0.0112(4) 0.0507(13) Uani 1 1 d . . . C5 C -0.2402(4) -0.0867(5) 0.0970(4) 0.0529(14) Uani 1 1 d . . . H5 H -0.2709 -0.1570 0.0955 0.063 Uiso 1 1 calc R . . C6 C -0.1887(4) -0.0373(5) 0.1828(4) 0.0517(14) Uani 1 1 d . . . H6 H -0.1841 -0.0743 0.2406 0.062 Uiso 1 1 calc R . . C7 C -0.0958(3) 0.3567(5) 0.2569(4) 0.0433(12) Uani 1 1 d . . . C8 C -0.0537(4) 0.4626(5) 0.2637(4) 0.0542(15) Uani 1 1 d . . . H8 H 0.0109 0.4686 0.2954 0.065 Uiso 1 1 calc R . . C9 C -0.1069(4) 0.5630(6) 0.2231(4) 0.0613(16) Uani 1 1 d . . . H9 H -0.0786 0.6358 0.2283 0.074 Uiso 1 1 calc R . . C10 C -0.2011(5) 0.5502(6) 0.1759(4) 0.0628(17) Uani 1 1 d . . . H10 H -0.2374 0.6155 0.1482 0.075 Uiso 1 1 calc R . . C11 C -0.2432(4) 0.4443(6) 0.1684(4) 0.0588(16) Uani 1 1 d . . . H11 H -0.3077 0.4376 0.1355 0.071 Uiso 1 1 calc R . . C12 C -0.1917(4) 0.3490(5) 0.2084(4) 0.0521(14) Uani 1 1 d . . . H12 H -0.2211 0.2770 0.2034 0.063 Uiso 1 1 calc R . . C13 C 0.0004(4) 0.2382(4) 0.4372(4) 0.0422(13) Uani 1 1 d . . . C14 C -0.0417(3) 0.1659(5) 0.4819(4) 0.0487(13) Uani 1 1 d . . . H14 H -0.0854 0.1109 0.4454 0.058 Uiso 1 1 calc R . . C15 C -0.0194(4) 0.1749(6) 0.5810(4) 0.0603(16) Uani 1 1 d . . . H15 H -0.0476 0.1260 0.6121 0.072 Uiso 1 1 calc R . . C16 C 0.0444(5) 0.2562(5) 0.6333(4) 0.0558(16) Uani 1 1 d . . . H16 H 0.0593 0.2628 0.7004 0.067 Uiso 1 1 calc R . . C17 C 0.0865(4) 0.3275(5) 0.5894(4) 0.0576(16) Uani 1 1 d . . . H17 H 0.1305 0.3821 0.6261 0.069 Uiso 1 1 calc R . . C18 C 0.0635(4) 0.3188(5) 0.4900(4) 0.0508(13) Uani 1 1 d . . . H18 H 0.0914 0.3683 0.4590 0.061 Uiso 1 1 calc R . . C19 C 0.0676(3) 0.2373(5) 0.1619(4) 0.0404(13) Uani 1 1 d . . . C20 C 0.0647(4) 0.1377(5) 0.1131(4) 0.0526(14) Uani 1 1 d . . . H20 H 0.0814 0.0677 0.1475 0.063 Uiso 1 1 calc R . . C21 C 0.0375(5) 0.1373(6) 0.0127(4) 0.0654(17) Uani 1 1 d . . . H21 H 0.0354 0.0677 -0.0206 0.079 Uiso 1 1 calc R . . C22 C 0.0139(5) 0.2385(6) -0.0364(5) 0.0626(18) Uani 1 1 d . . . H22 H -0.0059 0.2384 -0.1043 0.075 Uiso 1 1 calc R . . C23 C 0.0184(5) 0.3392(7) 0.0106(5) 0.0726(19) Uani 1 1 d . . . H23 H 0.0034 0.4090 -0.0243 0.087 Uiso 1 1 calc R . . C24 C 0.0450(4) 0.3396(6) 0.1091(4) 0.0587(15) Uani 1 1 d . . . H24 H 0.0479 0.4101 0.1417 0.070 Uiso 1 1 calc R . . C25 C 0.1571(3) 0.1118(4) 0.3418(4) 0.0411(12) Uani 1 1 d . . . C26 C 0.1159(4) 0.0054(5) 0.3270(4) 0.0528(14) Uani 1 1 d . . . H26 H 0.0522 -0.0004 0.2892 0.063 Uiso 1 1 calc R . . C27 C 0.1647(4) -0.0930(6) 0.3656(4) 0.0564(15) Uani 1 1 d . . . H27 H 0.1353 -0.1656 0.3530 0.068 Uiso 1 1 calc R . . C28 C 0.2563(5) -0.0845(6) 0.4227(4) 0.0640(18) Uani 1 1 d . . . H28 H 0.2903 -0.1516 0.4498 0.077 Uiso 1 1 calc R . . C29 C 0.2986(5) 0.0192(7) 0.4406(5) 0.080(2) Uani 1 1 d . . . H29 H 0.3618 0.0242 0.4804 0.096 Uiso 1 1 calc R . . C30 C 0.2496(4) 0.1181(5) 0.4007(4) 0.0586(16) Uani 1 1 d . . . H30 H 0.2795 0.1903 0.4137 0.070 Uiso 1 1 calc R . . C31 C -0.3029(4) -0.0811(6) -0.0812(5) 0.0627(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0431(7) 0.0518(9) 0.0358(7) -0.0048(7) 0.0160(6) -0.0052(7) P2 0.0449(7) 0.0550(9) 0.0440(8) -0.0015(6) 0.0189(6) 0.0022(6) N1 0.047(2) 0.044(3) 0.048(2) -0.011(2) 0.021(2) -0.007(2) N2 0.074(4) 0.078(4) 0.062(3) -0.013(3) 0.001(3) -0.002(3) C1 0.044(3) 0.048(3) 0.047(3) -0.007(2) 0.018(2) -0.002(2) C2 0.036(2) 0.044(3) 0.052(3) -0.003(2) 0.015(2) 0.001(2) C3 0.052(3) 0.048(4) 0.047(3) -0.009(3) 0.017(2) -0.002(3) C4 0.050(3) 0.046(4) 0.050(3) -0.013(3) 0.012(2) 0.003(3) C5 0.051(3) 0.045(3) 0.062(3) -0.008(3) 0.020(3) -0.004(3) C6 0.048(3) 0.054(4) 0.051(3) -0.002(3) 0.016(3) -0.002(3) C7 0.042(3) 0.058(4) 0.038(3) -0.006(2) 0.023(2) -0.002(2) C8 0.051(3) 0.063(4) 0.052(3) -0.009(3) 0.025(3) -0.006(3) C9 0.067(4) 0.058(4) 0.065(4) 0.001(3) 0.032(3) 0.002(3) C10 0.068(4) 0.071(5) 0.051(3) 0.007(3) 0.024(3) 0.019(4) C11 0.054(3) 0.058(5) 0.059(4) -0.002(3) 0.016(3) 0.014(3) C12 0.052(3) 0.060(4) 0.044(3) -0.014(3) 0.016(2) -0.006(3) C13 0.046(3) 0.039(3) 0.042(3) -0.003(2) 0.017(3) 0.009(2) C14 0.044(3) 0.058(4) 0.043(3) -0.002(3) 0.016(2) -0.010(3) C15 0.061(3) 0.078(5) 0.042(3) 0.003(3) 0.020(3) 0.000(3) C16 0.068(4) 0.061(4) 0.035(3) -0.007(3) 0.016(3) 0.003(3) C17 0.061(3) 0.061(4) 0.041(3) -0.011(3) 0.009(3) 0.005(3) C18 0.058(3) 0.047(3) 0.048(3) -0.010(3) 0.020(2) -0.013(3) C19 0.034(3) 0.049(3) 0.044(3) 0.006(2) 0.021(2) 0.004(2) C20 0.068(3) 0.054(4) 0.042(3) 0.007(3) 0.028(3) 0.011(3) C21 0.078(4) 0.080(5) 0.045(3) -0.005(3) 0.031(3) 0.003(4) C22 0.061(4) 0.082(5) 0.050(4) 0.018(3) 0.027(3) 0.018(3) C23 0.086(5) 0.079(5) 0.064(4) 0.031(4) 0.042(4) 0.027(4) C24 0.071(4) 0.058(4) 0.058(4) 0.007(3) 0.036(3) 0.006(3) C25 0.047(3) 0.039(3) 0.042(3) -0.001(2) 0.023(2) 0.003(2) C26 0.050(3) 0.063(4) 0.047(3) 0.005(3) 0.021(3) -0.001(3) C27 0.056(3) 0.069(4) 0.046(3) -0.001(3) 0.021(3) 0.006(3) C28 0.076(4) 0.070(5) 0.048(3) 0.009(3) 0.026(3) 0.010(4) C29 0.057(4) 0.087(6) 0.079(5) 0.007(4) 0.007(4) 0.009(4) C30 0.059(3) 0.048(4) 0.060(4) -0.004(3) 0.013(3) 0.003(3) C31 0.056(3) 0.052(4) 0.069(4) -0.023(3) 0.012(3) -0.002(3) _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 N1 1.572(5) . ? P1 C7 1.793(6) . ? P1 C13 1.823(5) . ? P1 P2 2.2451(16) . ? P2 C25 1.841(5) . ? P2 C19 1.843(5) . ? N1 C1 1.382(7) . ? N2 C31 1.140(7) . ? C1 C2 1.408(7) . ? C1 C6 1.437(8) . ? C2 C3 1.393(7) . ? C2 H2 0.9500 . ? C3 C4 1.369(8) . ? C3 H3 0.9500 . ? C4 C5 1.400(8) . ? C4 C31 1.446(8) . ? C5 C6 1.366(7) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.389(8) . ? C7 C12 1.410(7) . ? C8 C9 1.437(9) . ? C8 H8 0.9500 . ? C9 C10 1.389(9) . ? C9 H9 0.9500 . ? C10 C11 1.389(9) . ? C10 H10 0.9500 . ? C11 C12 1.374(8) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C18 1.381(8) . ? C13 C14 1.396(7) . ? C14 C15 1.401(7) . ? C14 H14 0.9500 . ? C15 C16 1.390(9) . ? C15 H15 0.9500 . ? C16 C17 1.381(9) . ? C16 H16 0.9500 . ? C17 C18 1.405(7) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.368(8) . ? C19 C24 1.405(8) . ? C20 C21 1.407(7) . ? C20 H20 0.9500 . ? C21 C22 1.368(9) . ? C21 H21 0.9500 . ? C22 C23 1.361(10) . ? C22 H22 0.9500 . ? C23 C24 1.381(9) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C26 1.381(8) . ? C25 C30 1.392(8) . ? C26 C27 1.382(8) . ? C26 H26 0.9500 . ? C27 C28 1.377(9) . ? C27 H27 0.9500 . ? C28 C29 1.359(10) . ? C28 H28 0.9500 . ? C29 C30 1.393(10) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? 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 C7 115.1(3) . . ? N1 P1 C13 105.5(2) . . ? C7 P1 C13 107.1(2) . . ? N1 P1 P2 121.68(17) . . ? C7 P1 P2 104.68(17) . . ? C13 P1 P2 101.16(19) . . ? C25 P2 C19 105.3(2) . . ? C25 P2 P1 101.02(17) . . ? C19 P2 P1 101.32(17) . . ? C1 N1 P1 131.3(4) . . ? N1 C1 C2 124.2(5) . . ? N1 C1 C6 118.7(5) . . ? C2 C1 C6 117.1(5) . . ? C3 C2 C1 119.7(5) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C4 C3 C2 122.0(5) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C3 C4 C5 119.6(5) . . ? C3 C4 C31 118.7(6) . . ? C5 C4 C31 121.6(6) . . ? C6 C5 C4 119.8(5) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C1 121.8(5) . . ? C5 C6 H6 119.1 . . ? C1 C6 H6 119.1 . . ? C8 C7 C12 118.9(5) . . ? C8 C7 P1 123.0(4) . . ? C12 C7 P1 118.1(4) . . ? C7 C8 C9 120.6(5) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C10 C9 C8 117.9(6) . . ? C10 C9 H9 121.0 . . ? C8 C9 H9 121.0 . . ? C9 C10 C11 121.5(6) . . ? C9 C10 H10 119.2 . . ? C11 C10 H10 119.2 . . ? C12 C11 C10 120.0(6) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C7 121.0(6) . . ? C11 C12 H12 119.5 . . ? C7 C12 H12 119.5 . . ? C18 C13 C14 120.3(5) . . ? C18 C13 P1 121.0(4) . . ? C14 C13 P1 118.6(4) . . ? C13 C14 C15 119.8(5) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C16 C15 C14 119.3(6) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C17 C16 C15 121.1(5) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C16 C17 C18 119.4(6) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C13 C18 C17 120.0(5) . . ? C13 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C20 C19 C24 118.1(5) . . ? C20 C19 P2 125.2(4) . . ? C24 C19 P2 116.7(4) . . ? C19 C20 C21 121.0(5) . . ? C19 C20 H20 119.5 . . ? C21 C20 H20 119.5 . . ? C22 C21 C20 119.2(6) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? C23 C22 C21 121.1(6) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C22 C23 C24 119.8(6) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C23 C24 C19 120.9(6) . . ? C23 C24 H24 119.6 . . ? C19 C24 H24 119.6 . . ? C26 C25 C30 117.7(5) . . ? C26 C25 P2 126.7(4) . . ? C30 C25 P2 115.6(4) . . ? C25 C26 C27 121.9(5) . . ? C25 C26 H26 119.0 . . ? C27 C26 H26 119.0 . . ? C28 C27 C26 119.1(6) . . ? C28 C27 H27 120.4 . . ? C26 C27 H27 120.4 . . ? C29 C28 C27 120.6(6) . . ? C29 C28 H28 119.7 . . ? C27 C28 H28 119.7 . . ? C28 C29 C30 120.2(6) . . ? C28 C29 H29 119.9 . . ? C30 C29 H29 119.9 . . ? C25 C30 C29 120.5(6) . . ? C25 C30 H30 119.8 . . ? C29 C30 H30 119.8 . . ? N2 C31 C4 179.5(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 P1 P2 C25 -45.2(2) . . . . ? C7 P1 P2 C25 -177.8(3) . . . . ? C13 P1 P2 C25 71.0(2) . . . . ? N1 P1 P2 C19 63.1(3) . . . . ? C7 P1 P2 C19 -69.5(2) . . . . ? C13 P1 P2 C19 179.2(2) . . . . ? C7 P1 N1 C1 54.9(6) . . . . ? C13 P1 N1 C1 172.7(5) . . . . ? P2 P1 N1 C1 -73.3(5) . . . . ? P1 N1 C1 C2 2.3(8) . . . . ? P1 N1 C1 C6 -178.6(4) . . . . ? N1 C1 C2 C3 -180.0(5) . . . . ? C6 C1 C2 C3 0.9(7) . . . . ? C1 C2 C3 C4 0.5(8) . . . . ? C2 C3 C4 C5 -1.7(8) . . . . ? C2 C3 C4 C31 178.3(5) . . . . ? C3 C4 C5 C6 1.4(8) . . . . ? C31 C4 C5 C6 -178.6(5) . . . . ? C4 C5 C6 C1 0.1(8) . . . . ? N1 C1 C6 C5 179.6(5) . . . . ? C2 C1 C6 C5 -1.3(7) . . . . ? N1 P1 C7 C8 -170.0(4) . . . . ? C13 P1 C7 C8 73.1(5) . . . . ? P2 P1 C7 C8 -33.8(5) . . . . ? N1 P1 C7 C12 10.2(5) . . . . ? C13 P1 C7 C12 -106.7(4) . . . . ? P2 P1 C7 C12 146.4(4) . . . . ? C12 C7 C8 C9 0.8(8) . . . . ? P1 C7 C8 C9 -179.0(4) . . . . ? C7 C8 C9 C10 -1.0(8) . . . . ? C8 C9 C10 C11 0.4(9) . . . . ? C9 C10 C11 C12 0.3(9) . . . . ? C10 C11 C12 C7 -0.5(8) . . . . ? C8 C7 C12 C11 -0.1(8) . . . . ? P1 C7 C12 C11 179.7(4) . . . . ? N1 P1 C13 C18 169.9(5) . . . . ? C7 P1 C13 C18 -67.1(5) . . . . ? P2 P1 C13 C18 42.3(5) . . . . ? N1 P1 C13 C14 -13.1(5) . . . . ? C7 P1 C13 C14 110.0(4) . . . . ? P2 P1 C13 C14 -140.7(4) . . . . ? C18 C13 C14 C15 -0.3(8) . . . . ? P1 C13 C14 C15 -177.4(4) . . . . ? C13 C14 C15 C16 0.2(9) . . . . ? C14 C15 C16 C17 -0.5(9) . . . . ? C15 C16 C17 C18 0.8(9) . . . . ? C14 C13 C18 C17 0.7(8) . . . . ? P1 C13 C18 C17 177.7(4) . . . . ? C16 C17 C18 C13 -1.0(9) . . . . ? C25 P2 C19 C20 14.2(5) . . . . ? P1 P2 C19 C20 -90.7(5) . . . . ? C25 P2 C19 C24 -164.3(4) . . . . ? P1 P2 C19 C24 90.8(4) . . . . ? C24 C19 C20 C21 -1.7(8) . . . . ? P2 C19 C20 C21 179.8(4) . . . . ? C19 C20 C21 C22 0.3(9) . . . . ? C20 C21 C22 C23 1.4(10) . . . . ? C21 C22 C23 C24 -1.6(11) . . . . ? C22 C23 C24 C19 0.1(10) . . . . ? C20 C19 C24 C23 1.5(9) . . . . ? P2 C19 C24 C23 -179.9(5) . . . . ? C19 P2 C25 C26 -65.1(5) . . . . ? P1 P2 C25 C26 40.0(5) . . . . ? C19 P2 C25 C30 115.9(4) . . . . ? P1 P2 C25 C30 -139.0(4) . . . . ? C30 C25 C26 C27 -2.5(8) . . . . ? P2 C25 C26 C27 178.5(4) . . . . ? C25 C26 C27 C28 1.8(8) . . . . ? C26 C27 C28 C29 -0.3(9) . . . . ? C27 C28 C29 C30 -0.5(11) . . . . ? C26 C25 C30 C29 1.7(9) . . . . ? P2 C25 C30 C29 -179.2(5) . . . . ? C28 C29 C30 C25 -0.3(11) . . . . ? C3 C4 C31 N2 -69(100) . . . . ? C5 C4 C31 N2 111(100) . . . . ? _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.948 _refine_diff_density_max 0.500 _refine_diff_density_min -0.406 _refine_diff_density_rms 0.070 data_4e _database_code_CSD 207374 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H20 F5 N P2' _chemical_formula_weight 551.41 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' F F 0.0171 0.0103 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.322(6) _cell_length_b 10.871(4) _cell_length_c 13.079(6) _cell_angle_alpha 108.49(4) _cell_angle_beta 95.79(4) _cell_angle_gamma 110.44(4) _cell_volume 1266.7(10) _cell_formula_units_Z 2 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 908 _cell_measurement_theta_min 2.1166 _cell_measurement_theta_max 19.0011 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 0.230 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; (See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166) ; _exptl_absorpt_correction_T_min 0.1980 _exptl_absorpt_correction_T_max 0.6670 _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'marresearch mar345 IPDS' _diffrn_measurement_method '60 images with deltaphi = 3 deg. and exp. time = 180 sec.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7700 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4197 _reflns_number_gt 2862 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'marresearch, mar345' _computing_cell_refinement 'Oxford Diffraction CrysAlis RED' _computing_data_reduction 'Oxford Diffraction CrysAlis RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0789P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0030(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4197 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1373 _refine_ls_wR_factor_gt 0.1250 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 0.12933(8) -0.04345(7) 0.18982(6) 0.0372(2) Uani 1 1 d . . . P2 P 0.22370(8) -0.01737(8) 0.36104(6) 0.0395(2) Uani 1 1 d . . . F1 F -0.07641(19) 0.13600(18) 0.20201(17) 0.0561(5) Uani 1 1 d . . . F2 F -0.0754(2) 0.3947(2) 0.27451(19) 0.0660(6) Uani 1 1 d . . . F3 F 0.1671(2) 0.62790(18) 0.31933(18) 0.0628(6) Uani 1 1 d . . . F4 F 0.4122(2) 0.59336(17) 0.28241(18) 0.0613(6) Uani 1 1 d . . . F5 F 0.41424(18) 0.33617(17) 0.21076(16) 0.0509(5) Uani 1 1 d . . . N1 N 0.1733(3) 0.0922(2) 0.1598(2) 0.0410(6) Uani 1 1 d . . . C1 C 0.1682(3) 0.2225(3) 0.2032(2) 0.0388(6) Uani 1 1 d . . . C2 C 0.0471(3) 0.2466(3) 0.2203(3) 0.0437(7) Uani 1 1 d . . . C3 C 0.0454(4) 0.3800(3) 0.2575(3) 0.0487(8) Uani 1 1 d . . . C4 C 0.1680(4) 0.4977(3) 0.2791(3) 0.0465(8) Uani 1 1 d . . . C5 C 0.2907(3) 0.4803(3) 0.2618(3) 0.0463(8) Uani 1 1 d . . . C6 C 0.2901(3) 0.3460(3) 0.2248(3) 0.0417(7) Uani 1 1 d . . . C7 C -0.0599(3) -0.1501(3) 0.1666(2) 0.0401(7) Uani 1 1 d . . . C8 C -0.1137(3) -0.2272(3) 0.2316(3) 0.0420(7) Uani 1 1 d . . . H8 H -0.0509 -0.2242 0.2916 0.050 Uiso 1 1 calc R . . C9 C -0.2581(3) -0.3076(3) 0.2087(3) 0.0468(7) Uani 1 1 d . . . H9 H -0.2941 -0.3599 0.2530 0.056 Uiso 1 1 calc R . . C10 C -0.3501(3) -0.3125(3) 0.1224(3) 0.0486(8) Uani 1 1 d . . . H10 H -0.4494 -0.3666 0.1078 0.058 Uiso 1 1 calc R . . C11 C -0.2970(3) -0.2380(3) 0.0568(3) 0.0499(8) Uani 1 1 d . . . H11 H -0.3603 -0.2425 -0.0036 0.060 Uiso 1 1 calc R . . C12 C -0.1529(3) -0.1574(3) 0.0781(2) 0.0447(7) Uani 1 1 d . . . H12 H -0.1175 -0.1070 0.0324 0.054 Uiso 1 1 calc R . . C13 C 0.1951(3) -0.1589(3) 0.0987(2) 0.0399(7) Uani 1 1 d . . . C14 C 0.2909(3) -0.1069(3) 0.0403(3) 0.0479(8) Uani 1 1 d . . . H14 H 0.3196 -0.0114 0.0462 0.057 Uiso 1 1 calc R . . C15 C 0.3449(4) -0.1938(4) -0.0266(3) 0.0554(9) Uani 1 1 d . . . H15 H 0.4095 -0.1579 -0.0673 0.067 Uiso 1 1 calc R . . C16 C 0.3059(4) -0.3314(3) -0.0347(3) 0.0551(9) Uani 1 1 d . . . H16 H 0.3451 -0.3899 -0.0794 0.066 Uiso 1 1 calc R . . C17 C 0.2101(4) -0.3842(3) 0.0221(3) 0.0539(8) Uani 1 1 d . . . H17 H 0.1820 -0.4800 0.0153 0.065 Uiso 1 1 calc R . . C18 C 0.1536(3) -0.2993(3) 0.0893(3) 0.0471(7) Uani 1 1 d . . . H18 H 0.0873 -0.3366 0.1284 0.057 Uiso 1 1 calc R . . C19 C 0.2162(3) 0.1539(3) 0.4332(2) 0.0416(7) Uani 1 1 d . . . C20 C 0.3331(4) 0.2825(3) 0.4797(3) 0.0480(8) Uani 1 1 d . . . H20 H 0.4254 0.2857 0.4751 0.058 Uiso 1 1 calc R . . C21 C 0.3169(4) 0.4071(4) 0.5332(3) 0.0591(9) Uani 1 1 d . . . H21 H 0.3982 0.4945 0.5653 0.071 Uiso 1 1 calc R . . C22 C 0.1836(5) 0.4045(4) 0.5400(3) 0.0635(10) Uani 1 1 d . . . H22 H 0.1724 0.4902 0.5742 0.076 Uiso 1 1 calc R . . C23 C 0.0649(4) 0.2746(4) 0.4960(3) 0.0569(9) Uani 1 1 d . . . H23 H -0.0271 0.2714 0.5022 0.068 Uiso 1 1 calc R . . C24 C 0.0821(3) 0.1509(3) 0.4435(3) 0.0483(8) Uani 1 1 d . . . H24 H 0.0014 0.0628 0.4141 0.058 Uiso 1 1 calc R . . C25 C 0.4057(3) 0.0165(3) 0.3472(2) 0.0401(7) Uani 1 1 d . . . C26 C 0.4910(3) 0.1203(3) 0.3125(3) 0.0475(8) Uani 1 1 d . . . H26 H 0.4567 0.1846 0.2973 0.057 Uiso 1 1 calc R . . C27 C 0.6249(4) 0.1289(4) 0.3006(3) 0.0536(8) Uani 1 1 d . . . H27 H 0.6833 0.2009 0.2789 0.064 Uiso 1 1 calc R . . C28 C 0.6746(3) 0.0339(4) 0.3199(3) 0.0518(8) Uani 1 1 d . . . H28 H 0.7659 0.0389 0.3096 0.062 Uiso 1 1 calc R . . C29 C 0.5919(3) -0.0679(3) 0.3542(3) 0.0473(7) Uani 1 1 d . . . H29 H 0.6268 -0.1323 0.3687 0.057 Uiso 1 1 calc R . . C30 C 0.4585(3) -0.0772(3) 0.3676(2) 0.0417(7) Uani 1 1 d . . . H30 H 0.4021 -0.1483 0.3910 0.050 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 0.0383(4) 0.0366(4) 0.0371(4) 0.0149(3) 0.0088(3) 0.0147(3) P2 0.0389(4) 0.0413(4) 0.0396(4) 0.0174(3) 0.0087(3) 0.0159(3) F1 0.0467(10) 0.0466(10) 0.0757(13) 0.0234(9) 0.0249(9) 0.0164(8) F2 0.0585(12) 0.0571(11) 0.0936(16) 0.0272(11) 0.0359(11) 0.0324(10) F3 0.0724(13) 0.0432(10) 0.0784(14) 0.0217(10) 0.0235(11) 0.0291(9) F4 0.0518(11) 0.0399(9) 0.0842(14) 0.0229(9) 0.0120(10) 0.0111(8) F5 0.0438(10) 0.0469(9) 0.0659(12) 0.0253(9) 0.0124(9) 0.0193(8) N1 0.0464(14) 0.0404(13) 0.0394(13) 0.0165(11) 0.0125(11) 0.0193(11) C1 0.0459(16) 0.0403(15) 0.0330(14) 0.0163(12) 0.0102(12) 0.0182(13) C2 0.0447(17) 0.0430(16) 0.0445(16) 0.0183(13) 0.0145(13) 0.0162(13) C3 0.0502(18) 0.0526(18) 0.0539(18) 0.0225(15) 0.0210(15) 0.0281(15) C4 0.057(2) 0.0375(15) 0.0503(18) 0.0189(13) 0.0150(15) 0.0219(14) C5 0.0466(18) 0.0407(16) 0.0477(17) 0.0190(14) 0.0071(14) 0.0123(13) C6 0.0407(16) 0.0441(16) 0.0439(16) 0.0186(13) 0.0100(13) 0.0195(13) C7 0.0454(16) 0.0367(14) 0.0370(15) 0.0122(12) 0.0091(13) 0.0168(12) C8 0.0414(16) 0.0454(16) 0.0409(15) 0.0198(13) 0.0107(12) 0.0161(13) C9 0.0480(18) 0.0444(16) 0.0477(17) 0.0194(14) 0.0156(14) 0.0153(13) C10 0.0393(16) 0.0476(17) 0.0503(18) 0.0130(15) 0.0101(14) 0.0131(13) C11 0.0463(18) 0.0538(19) 0.0447(17) 0.0137(15) 0.0044(14) 0.0209(15) C12 0.0523(18) 0.0449(16) 0.0390(16) 0.0168(13) 0.0134(14) 0.0207(14) C13 0.0376(15) 0.0388(14) 0.0413(15) 0.0142(12) 0.0073(12) 0.0145(12) C14 0.0511(18) 0.0433(16) 0.0505(18) 0.0178(14) 0.0170(15) 0.0189(14) C15 0.059(2) 0.0580(19) 0.055(2) 0.0202(16) 0.0255(16) 0.0277(16) C16 0.0532(19) 0.0528(18) 0.054(2) 0.0087(16) 0.0128(16) 0.0256(15) C17 0.059(2) 0.0429(17) 0.060(2) 0.0150(15) 0.0139(17) 0.0246(15) C18 0.0437(17) 0.0433(16) 0.0543(18) 0.0195(14) 0.0133(14) 0.0161(13) C19 0.0450(17) 0.0479(16) 0.0316(14) 0.0152(12) 0.0060(12) 0.0191(13) C20 0.0525(18) 0.0480(17) 0.0423(17) 0.0169(14) 0.0106(14) 0.0192(14) C21 0.078(3) 0.0461(18) 0.0484(19) 0.0147(15) 0.0147(17) 0.0220(17) C22 0.093(3) 0.063(2) 0.0476(19) 0.0190(17) 0.0214(19) 0.048(2) C23 0.069(2) 0.070(2) 0.0468(18) 0.0238(17) 0.0206(17) 0.0415(19) C24 0.0483(18) 0.0574(19) 0.0409(16) 0.0167(14) 0.0107(14) 0.0249(15) C25 0.0405(16) 0.0432(15) 0.0345(14) 0.0133(12) 0.0066(12) 0.0163(12) C26 0.0448(18) 0.0495(17) 0.0508(18) 0.0254(15) 0.0082(14) 0.0174(14) C27 0.0434(18) 0.063(2) 0.056(2) 0.0304(17) 0.0135(15) 0.0164(15) C28 0.0408(17) 0.069(2) 0.0490(18) 0.0238(16) 0.0124(14) 0.0244(16) C29 0.0472(18) 0.0538(18) 0.0446(17) 0.0170(14) 0.0075(14) 0.0270(14) C30 0.0458(17) 0.0414(15) 0.0371(15) 0.0129(13) 0.0088(13) 0.0189(13) _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 N1 1.571(3) . ? P1 C13 1.807(3) . ? P1 C7 1.824(3) . ? P1 P2 2.2379(16) . ? P2 C25 1.824(3) . ? P2 C19 1.834(3) . ? F1 C2 1.347(3) . ? F2 C3 1.343(4) . ? F3 C4 1.348(3) . ? F4 C5 1.342(4) . ? F5 C6 1.348(4) . ? N1 C1 1.371(4) . ? C1 C2 1.390(4) . ? C1 C6 1.405(4) . ? C2 C3 1.382(4) . ? C3 C4 1.373(4) . ? C4 C5 1.375(5) . ? C5 C6 1.382(4) . ? C7 C12 1.390(4) . ? C7 C8 1.398(4) . ? C8 C9 1.382(4) . ? C8 H8 0.9500 . ? C9 C10 1.375(5) . ? C9 H9 0.9500 . ? C10 C11 1.385(5) . ? C10 H10 0.9500 . ? C11 C12 1.382(5) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.385(4) . ? C13 C18 1.393(4) . ? C14 C15 1.382(5) . ? C14 H14 0.9500 . ? C15 C16 1.372(5) . ? C15 H15 0.9500 . ? C16 C17 1.372(5) . ? C16 H16 0.9500 . ? C17 C18 1.389(5) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.383(4) . ? C19 C24 1.395(4) . ? C20 C21 1.389(5) . ? C20 H20 0.9500 . ? C21 C22 1.380(6) . ? C21 H21 0.9500 . ? C22 C23 1.400(5) . ? C22 H22 0.9500 . ? C23 C24 1.385(5) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C30 1.391(4) . ? C25 C26 1.401(4) . ? C26 C27 1.380(5) . ? C26 H26 0.9500 . ? C27 C28 1.380(5) . ? C27 H27 0.9500 . ? C28 C29 1.373(5) . ? C28 H28 0.9500 . ? C29 C30 1.378(4) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? 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 C13 105.16(14) . . ? N1 P1 C7 118.17(14) . . ? C13 P1 C7 105.21(14) . . ? N1 P1 P2 117.82(11) . . ? C13 P1 P2 104.91(11) . . ? C7 P1 P2 104.19(11) . . ? C25 P2 C19 107.85(14) . . ? C25 P2 P1 97.95(11) . . ? C19 P2 P1 96.40(11) . . ? C1 N1 P1 135.2(2) . . ? N1 C1 C2 125.8(3) . . ? N1 C1 C6 119.9(3) . . ? C2 C1 C6 114.1(3) . . ? F1 C2 C3 116.9(3) . . ? F1 C2 C1 119.5(3) . . ? C3 C2 C1 123.7(3) . . ? F2 C3 C4 120.0(3) . . ? F2 C3 C2 120.0(3) . . ? C4 C3 C2 120.0(3) . . ? F3 C4 C3 119.8(3) . . ? F3 C4 C5 121.2(3) . . ? C3 C4 C5 119.0(3) . . ? F4 C5 C4 120.3(3) . . ? F4 C5 C6 119.6(3) . . ? C4 C5 C6 120.1(3) . . ? F5 C6 C5 117.2(3) . . ? F5 C6 C1 119.7(2) . . ? C5 C6 C1 123.2(3) . . ? C12 C7 C8 119.3(3) . . ? C12 C7 P1 117.8(2) . . ? C8 C7 P1 122.9(2) . . ? C9 C8 C7 120.0(3) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C10 C9 C8 120.5(3) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 119.6(3) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C12 C11 C10 120.7(3) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C7 119.8(3) . . ? C11 C12 H12 120.1 . . ? C7 C12 H12 120.1 . . ? C14 C13 C18 119.5(3) . . ? C14 C13 P1 120.0(2) . . ? C18 C13 P1 120.5(2) . . ? C15 C14 C13 120.1(3) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C16 C15 C14 120.5(3) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C17 C16 C15 119.7(3) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 120.8(3) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C17 C18 C13 119.3(3) . . ? C17 C18 H18 120.3 . . ? C13 C18 H18 120.3 . . ? C20 C19 C24 118.8(3) . . ? C20 C19 P2 124.8(3) . . ? C24 C19 P2 116.3(2) . . ? C19 C20 C21 120.7(3) . . ? C19 C20 H20 119.6 . . ? C21 C20 H20 119.6 . . ? C22 C21 C20 120.4(3) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 C23 119.4(3) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? C24 C23 C22 119.7(4) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C23 C24 C19 120.8(3) . . ? C23 C24 H24 119.6 . . ? C19 C24 H24 119.6 . . ? C30 C25 C26 118.5(3) . . ? C30 C25 P2 114.9(2) . . ? C26 C25 P2 126.4(2) . . ? C27 C26 C25 120.0(3) . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C28 C27 C26 120.6(3) . . ? C28 C27 H27 119.7 . . ? C26 C27 H27 119.7 . . ? C29 C28 C27 119.8(3) . . ? C29 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? C28 C29 C30 120.3(3) . . ? C28 C29 H29 119.8 . . ? C30 C29 H29 119.8 . . ? C29 C30 C25 120.7(3) . . ? C29 C30 H30 119.6 . . ? C25 C30 H30 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 P1 P2 C25 -70.45(15) . . . . ? C13 P1 P2 C25 46.07(14) . . . . ? C7 P1 P2 C25 156.40(13) . . . . ? N1 P1 P2 C19 38.65(15) . . . . ? C13 P1 P2 C19 155.17(14) . . . . ? C7 P1 P2 C19 -94.51(14) . . . . ? C13 P1 N1 C1 -172.8(3) . . . . ? C7 P1 N1 C1 70.2(3) . . . . ? P2 P1 N1 C1 -56.4(3) . . . . ? P1 N1 C1 C2 -55.8(4) . . . . ? P1 N1 C1 C6 130.2(3) . . . . ? N1 C1 C2 F1 5.5(5) . . . . ? C6 C1 C2 F1 179.9(3) . . . . ? N1 C1 C2 C3 -175.5(3) . . . . ? C6 C1 C2 C3 -1.2(4) . . . . ? F1 C2 C3 F2 0.6(5) . . . . ? C1 C2 C3 F2 -178.4(3) . . . . ? F1 C2 C3 C4 179.2(3) . . . . ? C1 C2 C3 C4 0.2(5) . . . . ? F2 C3 C4 F3 1.2(5) . . . . ? C2 C3 C4 F3 -177.5(3) . . . . ? F2 C3 C4 C5 179.6(3) . . . . ? C2 C3 C4 C5 0.9(5) . . . . ? F3 C4 C5 F4 -1.5(5) . . . . ? C3 C4 C5 F4 -179.9(3) . . . . ? F3 C4 C5 C6 177.3(3) . . . . ? C3 C4 C5 C6 -1.1(5) . . . . ? F4 C5 C6 F5 -0.4(4) . . . . ? C4 C5 C6 F5 -179.2(3) . . . . ? F4 C5 C6 C1 178.9(3) . . . . ? C4 C5 C6 C1 0.0(5) . . . . ? N1 C1 C6 F5 -5.0(4) . . . . ? C2 C1 C6 F5 -179.7(3) . . . . ? N1 C1 C6 C5 175.7(3) . . . . ? C2 C1 C6 C5 1.0(4) . . . . ? N1 P1 C7 C12 32.5(3) . . . . ? C13 P1 C7 C12 -84.5(3) . . . . ? P2 P1 C7 C12 165.4(2) . . . . ? N1 P1 C7 C8 -149.5(2) . . . . ? C13 P1 C7 C8 93.5(3) . . . . ? P2 P1 C7 C8 -16.6(3) . . . . ? C12 C7 C8 C9 -1.1(4) . . . . ? P1 C7 C8 C9 -179.0(2) . . . . ? C7 C8 C9 C10 -0.1(5) . . . . ? C8 C9 C10 C11 1.1(5) . . . . ? C9 C10 C11 C12 -0.9(5) . . . . ? C10 C11 C12 C7 -0.3(5) . . . . ? C8 C7 C12 C11 1.3(4) . . . . ? P1 C7 C12 C11 179.3(2) . . . . ? N1 P1 C13 C14 13.2(3) . . . . ? C7 P1 C13 C14 138.7(3) . . . . ? P2 P1 C13 C14 -111.7(3) . . . . ? N1 P1 C13 C18 -168.8(2) . . . . ? C7 P1 C13 C18 -43.3(3) . . . . ? P2 P1 C13 C18 66.2(3) . . . . ? C18 C13 C14 C15 -0.1(5) . . . . ? P1 C13 C14 C15 177.9(3) . . . . ? C13 C14 C15 C16 -0.9(5) . . . . ? C14 C15 C16 C17 1.5(5) . . . . ? C15 C16 C17 C18 -1.1(5) . . . . ? C16 C17 C18 C13 0.1(5) . . . . ? C14 C13 C18 C17 0.5(5) . . . . ? P1 C13 C18 C17 -177.5(3) . . . . ? C25 P2 C19 C20 -7.1(3) . . . . ? P1 P2 C19 C20 -107.6(3) . . . . ? C25 P2 C19 C24 174.8(2) . . . . ? P1 P2 C19 C24 74.3(2) . . . . ? C24 C19 C20 C21 -1.7(5) . . . . ? P2 C19 C20 C21 -179.8(3) . . . . ? C19 C20 C21 C22 -0.5(5) . . . . ? C20 C21 C22 C23 2.3(5) . . . . ? C21 C22 C23 C24 -1.9(5) . . . . ? C22 C23 C24 C19 -0.4(5) . . . . ? C20 C19 C24 C23 2.1(5) . . . . ? P2 C19 C24 C23 -179.6(3) . . . . ? C19 P2 C25 C30 138.2(2) . . . . ? P1 P2 C25 C30 -122.4(2) . . . . ? C19 P2 C25 C26 -45.7(3) . . . . ? P1 P2 C25 C26 53.7(3) . . . . ? C30 C25 C26 C27 -0.8(4) . . . . ? P2 C25 C26 C27 -176.7(2) . . . . ? C25 C26 C27 C28 1.6(5) . . . . ? C26 C27 C28 C29 -1.7(5) . . . . ? C27 C28 C29 C30 1.1(5) . . . . ? C28 C29 C30 C25 -0.3(4) . . . . ? C26 C25 C30 C29 0.1(4) . . . . ? P2 C25 C30 C29 176.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 0.403 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.064 data_4f _database_code_CSD 207375 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H24 F3 N P2, C H2 Cl2' _chemical_formula_sum 'C32 H26 Cl2 F3 N P2' _chemical_formula_weight 614.38 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' F F 0.0171 0.0103 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.087(2) _cell_length_b 10.647(5) _cell_length_c 15.187(7) _cell_angle_alpha 82.05(4) _cell_angle_beta 74.46(3) _cell_angle_gamma 67.64(3) _cell_volume 1452.0(10) _cell_formula_units_Z 2 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 1234 _cell_measurement_theta_min 1.42405 _cell_measurement_theta_max 19.3078 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.405 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.377 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; (See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166) ; _exptl_absorpt_correction_T_min 0.288 _exptl_absorpt_correction_T_max 0.733 _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'marresearch mar345 IPDS' _diffrn_measurement_method '60 images with deltaphi = 3 deg. and exp. time = 180 sec.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9435 _diffrn_reflns_av_R_equivalents 0.0739 _diffrn_reflns_av_sigmaI/netI 0.0794 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4805 _reflns_number_gt 3330 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'marresearch, mar345' _computing_cell_refinement 'Oxford Diffraction CrysAlis RED' _computing_data_reduction 'Oxford Diffraction CrysAlis RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1430P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4805 _refine_ls_number_parameters 390 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0933 _refine_ls_R_factor_gt 0.0748 _refine_ls_wR_factor_ref 0.2295 _refine_ls_wR_factor_gt 0.2041 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.098 _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 0.27732(10) 0.26235(9) 0.24090(7) 0.0406(3) Uani 1 1 d . . . P2 P 0.21160(10) 0.12337(9) 0.35521(7) 0.0428(3) Uani 1 1 d . . . F1 F 0.1020(3) 0.8198(2) 0.1414(2) 0.0685(7) Uani 1 1 d . . . F2 F 0.2074(3) 0.6158(3) 0.09403(17) 0.0593(6) Uani 1 1 d . . . F3 F -0.0040(2) 0.6737(2) 0.19063(18) 0.0574(6) Uani 1 1 d . . . N1 N 0.2089(3) 0.4221(3) 0.2460(2) 0.0444(7) Uani 1 1 d . . . C1 C 0.2451(4) 0.5131(4) 0.2831(3) 0.0408(8) Uani 1 1 d . . . C2 C 0.2050(4) 0.6489(4) 0.2470(3) 0.0422(8) Uani 1 1 d . . . C3 C 0.2321(4) 0.7471(4) 0.2840(3) 0.0500(9) Uani 1 1 d . . . H3 H 0.2029 0.8379 0.2594 0.060 Uiso 1 1 calc R . . C4 C 0.3012(4) 0.7142(4) 0.3560(3) 0.0525(10) Uani 1 1 d . . . H4 H 0.3200 0.7815 0.3805 0.063 Uiso 1 1 calc R . . C5 C 0.3421(4) 0.5826(4) 0.3915(3) 0.0520(10) Uani 1 1 d . . . H5 H 0.3881 0.5596 0.4415 0.062 Uiso 1 1 calc R . . C6 C 0.3169(4) 0.4830(4) 0.3554(3) 0.0454(9) Uani 1 1 d . . . H6 H 0.3489 0.3924 0.3801 0.054 Uiso 1 1 calc R . . C7 C 0.4783(4) 0.1929(4) 0.2139(3) 0.0424(8) Uani 1 1 d . . . C8 C 0.5510(4) 0.2786(4) 0.1655(3) 0.0477(9) Uani 1 1 d . . . H8 H 0.4955 0.3697 0.1503 0.057 Uiso 1 1 calc R . . C9 C 0.7051(4) 0.2310(4) 0.1393(3) 0.0547(10) Uani 1 1 d . . . H9 H 0.7540 0.2892 0.1053 0.066 Uiso 1 1 calc R . . C10 C 0.7858(5) 0.0996(5) 0.1630(3) 0.0561(10) Uani 1 1 d . . . H10 H 0.8905 0.0680 0.1468 0.067 Uiso 1 1 calc R . . C11 C 0.7142(4) 0.0135(4) 0.2104(3) 0.0557(10) Uani 1 1 d . . . H11 H 0.7705 -0.0777 0.2251 0.067 Uiso 1 1 calc R . . C12 C 0.5612(4) 0.0587(4) 0.2367(3) 0.0468(9) Uani 1 1 d . . . H12 H 0.5132 -0.0008 0.2697 0.056 Uiso 1 1 calc R . . C13 C 0.2192(4) 0.2197(4) 0.1498(3) 0.0451(8) Uani 1 1 d . . . C14 C 0.2779(4) 0.0880(4) 0.1184(3) 0.0487(9) Uani 1 1 d . . . H14 H 0.3512 0.0191 0.1443 0.058 Uiso 1 1 calc R . . C15 C 0.2297(5) 0.0565(5) 0.0490(3) 0.0568(10) Uani 1 1 d . . . H15 H 0.2704 -0.0332 0.0276 0.068 Uiso 1 1 calc R . . C16 C 0.1227(5) 0.1567(5) 0.0117(3) 0.0551(10) Uani 1 1 d . . . H16 H 0.0896 0.1351 -0.0352 0.066 Uiso 1 1 calc R . . C17 C 0.0628(4) 0.2887(5) 0.0419(3) 0.0532(10) Uani 1 1 d . . . H17 H -0.0106 0.3568 0.0157 0.064 Uiso 1 1 calc R . . C18 C 0.1109(4) 0.3207(4) 0.1107(3) 0.0483(9) Uani 1 1 d . . . H18 H 0.0705 0.4109 0.1313 0.058 Uiso 1 1 calc R . . C19 C 0.2242(4) 0.1994(4) 0.4524(3) 0.0421(8) Uani 1 1 d . . . C20 C 0.3631(4) 0.1551(4) 0.4738(3) 0.0453(8) Uani 1 1 d . . . H20 H 0.4451 0.0883 0.4380 0.054 Uiso 1 1 calc R . . C21 C 0.3818(4) 0.2079(4) 0.5468(3) 0.0488(9) Uani 1 1 d . . . H21 H 0.4766 0.1795 0.5592 0.059 Uiso 1 1 calc R . . C22 C 0.2621(5) 0.3016(4) 0.6010(3) 0.0552(10) Uani 1 1 d . . . H22 H 0.2747 0.3368 0.6511 0.066 Uiso 1 1 calc R . . C23 C 0.1234(4) 0.3445(4) 0.5827(3) 0.0524(10) Uani 1 1 d . . . H23 H 0.0416 0.4086 0.6206 0.063 Uiso 1 1 calc R . . C24 C 0.1037(4) 0.2942(4) 0.5092(3) 0.0476(9) Uani 1 1 d . . . H24 H 0.0084 0.3240 0.4973 0.057 Uiso 1 1 calc R . . C25 C 0.0123(4) 0.1778(4) 0.3630(3) 0.0415(8) Uani 1 1 d . . . C26 C -0.0467(4) 0.0750(4) 0.3903(3) 0.0484(9) Uani 1 1 d . . . H26 H 0.0154 -0.0147 0.4032 0.058 Uiso 1 1 calc R . . C27 C -0.1971(5) 0.1043(5) 0.3986(3) 0.0576(11) Uani 1 1 d . . . H27 H -0.2372 0.0346 0.4170 0.069 Uiso 1 1 calc R . . C28 C -0.2858(5) 0.2336(5) 0.3799(3) 0.0553(10) Uani 1 1 d . . . H28 H -0.3878 0.2532 0.3857 0.066 Uiso 1 1 calc R . . C29 C -0.2298(4) 0.3360(4) 0.3530(3) 0.0518(10) Uani 1 1 d . . . H29 H -0.2930 0.4255 0.3405 0.062 Uiso 1 1 calc R . . C30 C -0.0796(4) 0.3081(4) 0.3440(3) 0.0479(9) Uani 1 1 d . . . H30 H -0.0407 0.3785 0.3249 0.057 Uiso 1 1 calc R . . C31 C 0.1281(5) 0.6886(4) 0.1696(3) 0.0515(10) Uani 1 1 d . . . Cl1A Cl 0.2703(2) 0.4212(2) -0.16275(13) 0.0790(7) Uani 0.763(5) 1 d PD A 1 Cl2A Cl 0.4811(5) 0.3217(6) -0.0493(3) 0.130(2) Uani 0.763(5) 1 d PD A 1 C32A C 0.4122(7) 0.2830(7) -0.1265(6) 0.077(2) Uani 0.763(5) 1 d PD A 1 H32A H 0.3735 0.2100 -0.0998 0.092 Uiso 0.763(5) 1 calc PR A 1 H32B H 0.4933 0.2469 -0.1806 0.092 Uiso 0.763(5) 1 calc PR A 1 Cl1B Cl 0.3653(11) 0.2690(11) -0.1809(5) 0.119(4) Uani 0.237(5) 1 d PD A 2 Cl2B Cl 0.4464(17) 0.3787(16) -0.0467(9) 0.109(6) Uani 0.237(5) 1 d PD A 2 C32B C 0.385(4) 0.409(2) -0.1468(16) 0.121(13) Uani 0.237(5) 1 d PD A 2 H32C H 0.2882 0.4848 -0.1377 0.145 Uiso 0.237(5) 1 calc PR A 2 H32D H 0.4550 0.4375 -0.1964 0.145 Uiso 0.237(5) 1 calc PR A 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 P1 0.0405(5) 0.0366(5) 0.0482(6) -0.0036(4) -0.0110(4) -0.0168(4) P2 0.0422(5) 0.0386(5) 0.0507(6) -0.0019(4) -0.0102(4) -0.0183(4) F1 0.0849(18) 0.0470(13) 0.087(2) 0.0188(13) -0.0440(15) -0.0300(12) F2 0.0651(15) 0.0663(15) 0.0511(14) -0.0004(12) -0.0159(11) -0.0279(12) F3 0.0515(13) 0.0567(14) 0.0723(17) 0.0033(12) -0.0248(11) -0.0237(11) N1 0.0419(16) 0.0390(16) 0.056(2) -0.0024(14) -0.0127(13) -0.0174(13) C1 0.0357(18) 0.0370(18) 0.052(2) -0.0025(16) -0.0090(14) -0.0161(14) C2 0.0381(18) 0.0391(18) 0.050(2) -0.0057(16) -0.0094(15) -0.0133(15) C3 0.052(2) 0.039(2) 0.063(3) -0.0047(18) -0.0124(18) -0.0208(17) C4 0.053(2) 0.050(2) 0.065(3) -0.0142(19) -0.0142(18) -0.0250(18) C5 0.050(2) 0.054(2) 0.058(3) -0.0069(19) -0.0143(17) -0.0234(18) C6 0.043(2) 0.0379(18) 0.058(2) -0.0031(17) -0.0164(16) -0.0141(15) C7 0.0395(19) 0.0418(19) 0.049(2) -0.0041(16) -0.0102(14) -0.0169(15) C8 0.045(2) 0.045(2) 0.054(2) -0.0022(17) -0.0108(16) -0.0184(16) C9 0.054(2) 0.056(2) 0.058(3) -0.008(2) -0.0027(18) -0.030(2) C10 0.045(2) 0.064(3) 0.061(3) -0.012(2) -0.0064(17) -0.0222(19) C11 0.047(2) 0.048(2) 0.065(3) -0.009(2) -0.0125(19) -0.0081(17) C12 0.041(2) 0.045(2) 0.054(2) -0.0048(17) -0.0070(16) -0.0168(16) C13 0.049(2) 0.047(2) 0.045(2) -0.0016(16) -0.0084(16) -0.0249(16) C14 0.057(2) 0.043(2) 0.053(2) 0.0027(17) -0.0149(17) -0.0252(18) C15 0.070(3) 0.057(2) 0.054(3) -0.009(2) -0.011(2) -0.034(2) C16 0.058(2) 0.067(3) 0.055(2) -0.007(2) -0.0153(19) -0.035(2) C17 0.046(2) 0.060(2) 0.058(3) -0.005(2) -0.0123(17) -0.0239(19) C18 0.043(2) 0.046(2) 0.057(2) -0.0073(18) -0.0115(16) -0.0167(16) C19 0.0440(19) 0.0373(18) 0.050(2) 0.0022(15) -0.0101(15) -0.0220(15) C20 0.046(2) 0.0397(19) 0.051(2) 0.0025(16) -0.0117(16) -0.0180(15) C21 0.052(2) 0.045(2) 0.057(2) 0.0031(18) -0.0201(18) -0.0233(17) C22 0.064(3) 0.058(2) 0.052(2) -0.0074(19) -0.0115(19) -0.031(2) C23 0.048(2) 0.055(2) 0.054(2) -0.0120(19) -0.0002(17) -0.0230(18) C24 0.0413(19) 0.048(2) 0.053(2) -0.0050(17) -0.0031(16) -0.0196(16) C25 0.0399(19) 0.0396(19) 0.047(2) -0.0085(15) -0.0057(14) -0.0169(15) C26 0.054(2) 0.042(2) 0.055(2) 0.0000(17) -0.0171(17) -0.0226(17) C27 0.062(3) 0.069(3) 0.058(3) 0.003(2) -0.016(2) -0.040(2) C28 0.050(2) 0.066(3) 0.062(3) 0.003(2) -0.0202(18) -0.031(2) C29 0.044(2) 0.052(2) 0.060(3) -0.0011(19) -0.0112(17) -0.0179(17) C30 0.044(2) 0.049(2) 0.055(2) -0.0014(17) -0.0097(16) -0.0226(17) C31 0.056(2) 0.044(2) 0.062(3) 0.0041(18) -0.0188(19) -0.0243(17) Cl1A 0.0812(13) 0.0853(14) 0.0739(12) 0.0057(9) -0.0326(9) -0.0270(10) Cl2A 0.0728(16) 0.239(6) 0.0746(19) 0.023(3) -0.0255(12) -0.057(3) C32A 0.059(4) 0.065(4) 0.096(6) -0.002(4) -0.003(3) -0.022(3) Cl1B 0.153(7) 0.183(10) 0.079(5) -0.001(5) -0.026(4) -0.127(8) Cl2B 0.159(13) 0.173(12) 0.077(5) 0.010(6) -0.045(7) -0.142(12) C32B 0.17(3) 0.10(2) 0.13(3) -0.019(19) 0.00(2) -0.11(2) _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 N1 1.578(3) . ? P1 C13 1.809(4) . ? P1 C7 1.823(4) . ? P1 P2 2.2498(18) . ? P2 C19 1.833(4) . ? P2 C25 1.843(4) . ? F1 C31 1.349(5) . ? F2 C31 1.357(5) . ? F3 C31 1.349(5) . ? N1 C1 1.385(5) . ? C1 C6 1.410(5) . ? C1 C2 1.417(5) . ? C2 C3 1.395(5) . ? C2 C31 1.505(6) . ? C3 C4 1.386(6) . ? C3 H3 0.9500 . ? C4 C5 1.377(6) . ? C4 H4 0.9500 . ? C5 C6 1.389(5) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.394(5) . ? C7 C12 1.404(5) . ? C8 C9 1.399(6) . ? C8 H8 0.9500 . ? C9 C10 1.378(6) . ? C9 H9 0.9500 . ? C10 C11 1.387(6) . ? C10 H10 0.9500 . ? C11 C12 1.389(5) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.395(5) . ? C13 C18 1.407(5) . ? C14 C15 1.398(6) . ? C14 H14 0.9500 . ? C15 C16 1.381(6) . ? C15 H15 0.9500 . ? C16 C17 1.391(6) . ? C16 H16 0.9500 . ? C17 C18 1.393(6) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C24 1.410(5) . ? C19 C20 1.411(5) . ? C20 C21 1.395(6) . ? C20 H20 0.9500 . ? C21 C22 1.381(6) . ? C21 H21 0.9500 . ? C22 C23 1.389(6) . ? C22 H22 0.9500 . ? C23 C24 1.392(6) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C30 1.386(5) . ? C25 C26 1.400(5) . ? C26 C27 1.402(6) . ? C26 H26 0.9500 . ? C27 C28 1.366(6) . ? C27 H27 0.9500 . ? C28 C29 1.377(6) . ? C28 H28 0.9500 . ? C29 C30 1.400(5) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? Cl1A C32A 1.764(7) . ? Cl2A C32A 1.678(9) . ? C32A H32A 0.9900 . ? C32A H32B 0.9900 . ? Cl1B C32B 1.734(16) . ? Cl2B C32B 1.738(19) . ? C32B H32C 0.9900 . ? C32B H32D 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 N1 P1 C13 106.76(18) . . ? N1 P1 C7 113.98(17) . . ? C13 P1 C7 107.47(18) . . ? N1 P1 P2 122.49(14) . . ? C13 P1 P2 100.60(13) . . ? C7 P1 P2 104.03(13) . . ? C19 P2 C25 104.80(17) . . ? C19 P2 P1 99.70(13) . . ? C25 P2 P1 101.46(13) . . ? C1 N1 P1 132.2(3) . . ? N1 C1 C6 125.5(3) . . ? N1 C1 C2 118.0(3) . . ? C6 C1 C2 116.5(3) . . ? C3 C2 C1 120.9(4) . . ? C3 C2 C31 119.5(3) . . ? C1 C2 C31 119.5(3) . . ? C4 C3 C2 121.0(4) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C5 C4 C3 119.0(4) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 121.0(4) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C1 121.6(4) . . ? C5 C6 H6 119.2 . . ? C1 C6 H6 119.2 . . ? C8 C7 C12 119.4(3) . . ? C8 C7 P1 117.0(3) . . ? C12 C7 P1 123.6(3) . . ? C7 C8 C9 120.3(4) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C10 C9 C8 119.9(4) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 120.0(4) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C12 120.9(4) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C11 C12 C7 119.4(4) . . ? C11 C12 H12 120.3 . . ? C7 C12 H12 120.3 . . ? C14 C13 C18 119.2(4) . . ? C14 C13 P1 121.4(3) . . ? C18 C13 P1 119.4(3) . . ? C13 C14 C15 120.5(4) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C16 C15 C14 119.6(4) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 120.8(4) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C16 C17 C18 119.8(4) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C17 C18 C13 120.1(4) . . ? C17 C18 H18 120.0 . . ? C13 C18 H18 120.0 . . ? C24 C19 C20 118.1(4) . . ? C24 C19 P2 124.5(3) . . ? C20 C19 P2 117.4(3) . . ? C21 C20 C19 120.9(4) . . ? C21 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C22 C21 C20 119.9(4) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C21 C22 C23 120.4(4) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C22 C23 C24 120.3(4) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C23 C24 C19 120.4(4) . . ? C23 C24 H24 119.8 . . ? C19 C24 H24 119.8 . . ? C30 C25 C26 119.2(3) . . ? C30 C25 P2 125.8(3) . . ? C26 C25 P2 115.0(3) . . ? C25 C26 C27 120.1(4) . . ? C25 C26 H26 119.9 . . ? C27 C26 H26 119.9 . . ? C28 C27 C26 119.7(4) . . ? C28 C27 H27 120.2 . . ? C26 C27 H27 120.2 . . ? C27 C28 C29 121.0(4) . . ? C27 C28 H28 119.5 . . ? C29 C28 H28 119.5 . . ? C28 C29 C30 119.9(4) . . ? C28 C29 H29 120.0 . . ? C30 C29 H29 120.0 . . ? C25 C30 C29 120.0(4) . . ? C25 C30 H30 120.0 . . ? C29 C30 H30 120.0 . . ? F1 C31 F3 105.9(3) . . ? F1 C31 F2 105.3(3) . . ? F3 C31 F2 105.7(3) . . ? F1 C31 C2 112.1(3) . . ? F3 C31 C2 113.9(3) . . ? F2 C31 C2 113.2(3) . . ? Cl2A C32A Cl1A 114.2(5) . . ? Cl2A C32A H32A 108.7 . . ? Cl1A C32A H32A 108.7 . . ? Cl2A C32A H32B 108.7 . . ? Cl1A C32A H32B 108.7 . . ? H32A C32A H32B 107.6 . . ? Cl1B C32B Cl2B 113.8(13) . . ? Cl1B C32B H32C 108.8 . . ? Cl2B C32B H32C 108.8 . . ? Cl1B C32B H32D 108.8 . . ? Cl2B C32B H32D 108.8 . . ? H32C C32B H32D 107.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 P1 P2 C19 -47.62(19) . . . . ? C13 P1 P2 C19 -165.45(17) . . . . ? C7 P1 P2 C19 83.35(18) . . . . ? N1 P1 P2 C25 59.78(19) . . . . ? C13 P1 P2 C25 -58.06(18) . . . . ? C7 P1 P2 C25 -169.25(17) . . . . ? C13 P1 N1 C1 -160.0(4) . . . . ? C7 P1 N1 C1 -41.5(4) . . . . ? P2 P1 N1 C1 85.2(4) . . . . ? P1 N1 C1 C6 -25.9(6) . . . . ? P1 N1 C1 C2 155.3(3) . . . . ? N1 C1 C2 C3 177.1(3) . . . . ? C6 C1 C2 C3 -1.9(5) . . . . ? N1 C1 C2 C31 -1.1(5) . . . . ? C6 C1 C2 C31 179.9(3) . . . . ? C1 C2 C3 C4 1.0(6) . . . . ? C31 C2 C3 C4 179.2(4) . . . . ? C2 C3 C4 C5 -0.5(6) . . . . ? C3 C4 C5 C6 0.9(6) . . . . ? C4 C5 C6 C1 -1.9(6) . . . . ? N1 C1 C6 C5 -176.6(4) . . . . ? C2 C1 C6 C5 2.3(6) . . . . ? N1 P1 C7 C8 -25.4(4) . . . . ? C13 P1 C7 C8 92.7(3) . . . . ? P2 P1 C7 C8 -161.2(3) . . . . ? N1 P1 C7 C12 156.6(3) . . . . ? C13 P1 C7 C12 -85.3(4) . . . . ? P2 P1 C7 C12 20.8(4) . . . . ? C12 C7 C8 C9 0.5(6) . . . . ? P1 C7 C8 C9 -177.6(3) . . . . ? C7 C8 C9 C10 -1.3(6) . . . . ? C8 C9 C10 C11 1.9(7) . . . . ? C9 C10 C11 C12 -1.6(7) . . . . ? C10 C11 C12 C7 0.7(6) . . . . ? C8 C7 C12 C11 -0.2(6) . . . . ? P1 C7 C12 C11 177.8(3) . . . . ? N1 P1 C13 C14 170.6(3) . . . . ? C7 P1 C13 C14 48.0(4) . . . . ? P2 P1 C13 C14 -60.5(3) . . . . ? N1 P1 C13 C18 -10.4(4) . . . . ? C7 P1 C13 C18 -133.1(3) . . . . ? P2 P1 C13 C18 118.4(3) . . . . ? C18 C13 C14 C15 -0.1(6) . . . . ? P1 C13 C14 C15 178.9(3) . . . . ? C13 C14 C15 C16 -0.3(6) . . . . ? C14 C15 C16 C17 0.4(6) . . . . ? C15 C16 C17 C18 -0.1(6) . . . . ? C16 C17 C18 C13 -0.3(6) . . . . ? C14 C13 C18 C17 0.3(6) . . . . ? P1 C13 C18 C17 -178.7(3) . . . . ? C25 P2 C19 C24 -8.4(4) . . . . ? P1 P2 C19 C24 96.3(3) . . . . ? C25 P2 C19 C20 168.8(3) . . . . ? P1 P2 C19 C20 -86.5(3) . . . . ? C24 C19 C20 C21 -2.6(5) . . . . ? P2 C19 C20 C21 -180.0(3) . . . . ? C19 C20 C21 C22 2.1(6) . . . . ? C20 C21 C22 C23 -0.6(6) . . . . ? C21 C22 C23 C24 -0.4(7) . . . . ? C22 C23 C24 C19 -0.1(6) . . . . ? C20 C19 C24 C23 1.6(6) . . . . ? P2 C19 C24 C23 178.7(3) . . . . ? C19 P2 C25 C30 72.0(4) . . . . ? P1 P2 C25 C30 -31.3(4) . . . . ? C19 P2 C25 C26 -108.3(3) . . . . ? P1 P2 C25 C26 148.3(3) . . . . ? C30 C25 C26 C27 -0.3(6) . . . . ? P2 C25 C26 C27 -180.0(3) . . . . ? C25 C26 C27 C28 0.0(7) . . . . ? C26 C27 C28 C29 0.1(7) . . . . ? C27 C28 C29 C30 0.2(7) . . . . ? C26 C25 C30 C29 0.6(6) . . . . ? P2 C25 C30 C29 -179.8(3) . . . . ? C28 C29 C30 C25 -0.6(6) . . . . ? C3 C2 C31 F1 3.8(5) . . . . ? C1 C2 C31 F1 -178.0(3) . . . . ? C3 C2 C31 F3 -116.4(4) . . . . ? C1 C2 C31 F3 61.8(5) . . . . ? C3 C2 C31 F2 122.8(4) . . . . ? C1 C2 C31 F2 -59.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 0.682 _refine_diff_density_min -0.575 _refine_diff_density_rms 0.087 data_5 _database_code_CSD 207376 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H25 N P2' _chemical_formula_weight 461.45 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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' '-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 18.5448(16) _cell_length_b 12.7369(11) _cell_length_c 10.4063(8) _cell_angle_alpha 90.00 _cell_angle_beta 100.092(7) _cell_angle_gamma 90.00 _cell_volume 2420.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 3389 _cell_measurement_theta_min 2.26535 _cell_measurement_theta_max 28.3701 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; (See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166) ; _exptl_absorpt_correction_T_min 0.6550 _exptl_absorpt_correction_T_max 0.8990 _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(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 'Oxford Diffraction KM4/Sapphire CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6712 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0262 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.71 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2017 _reflns_number_gt 1745 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Oxford Diffraction CrysAlis CCD' _computing_cell_refinement 'Oxford Diffraction CrysAlis RED' _computing_data_reduction 'Oxford Diffraction CrysAlis RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0229P)^2^+5.3918P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2017 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0460 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.0959 _refine_ls_wR_factor_gt 0.0934 _refine_ls_goodness_of_fit_ref 1.147 _refine_ls_restrained_S_all 1.147 _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 0.07026(3) 0.09634(4) 0.20760(6) 0.01766(17) Uani 1 1 d . . . N1 N 0.0000 0.1710(2) 0.2500 0.0189(6) Uani 1 2 d S . . C1 C 0.0000 0.2853(2) 0.2500 0.0194(7) Uani 1 2 d S . . C2 C 0.03288(12) 0.34045(18) 0.3602(2) 0.0256(6) Uani 1 1 d . . . H2 H 0.0552 0.3034 0.4361 0.031 Uiso 1 1 calc R . . C3 C 0.03322(13) 0.45020(19) 0.3595(3) 0.0325(6) Uani 1 1 d . . . H3 H 0.0563 0.4876 0.4346 0.039 Uiso 1 1 calc R . . C4 C 0.0000 0.5044(3) 0.2500 0.0350(9) Uani 1 2 d S . . H4 H 0.0000 0.5790 0.2500 0.042 Uiso 1 2 calc SR . . C5 C 0.09935(11) 0.17501(17) 0.0782(2) 0.0196(5) Uani 1 1 d . . . C6 C 0.14563(12) 0.26276(18) 0.0995(2) 0.0244(5) Uani 1 1 d . . . H6 H 0.1640 0.2850 0.1862 0.029 Uiso 1 1 calc R . . C7 C 0.16484(13) 0.3174(2) -0.0047(3) 0.0312(6) Uani 1 1 d . . . H7 H 0.1965 0.3764 0.0108 0.037 Uiso 1 1 calc R . . C8 C 0.13784(13) 0.2860(2) -0.1315(3) 0.0335(6) Uani 1 1 d . . . H8 H 0.1508 0.3238 -0.2028 0.040 Uiso 1 1 calc R . . C9 C 0.09187(13) 0.1995(2) -0.1545(3) 0.0309(6) Uani 1 1 d . . . H9 H 0.0733 0.1782 -0.2415 0.037 Uiso 1 1 calc R . . C10 C 0.07312(12) 0.14418(19) -0.0504(2) 0.0237(5) Uani 1 1 d . . . H10 H 0.0421 0.0846 -0.0667 0.028 Uiso 1 1 calc R . . C11 C 0.14780(11) 0.11144(16) 0.3434(2) 0.0179(5) Uani 1 1 d . . . C12 C 0.13695(12) 0.11830(17) 0.4722(2) 0.0227(5) Uani 1 1 d . . . H12 H 0.0886 0.1258 0.4897 0.027 Uiso 1 1 calc R . . C13 C 0.19584(13) 0.11436(18) 0.5760(2) 0.0246(5) Uani 1 1 d . . . H13 H 0.1875 0.1199 0.6633 0.030 Uiso 1 1 calc R . . C14 C 0.26654(12) 0.10242(18) 0.5516(2) 0.0265(6) Uani 1 1 d . . . H14 H 0.3067 0.0999 0.6221 0.032 Uiso 1 1 calc R . . C15 C 0.27848(12) 0.09425(18) 0.4246(2) 0.0251(5) Uani 1 1 d . . . H15 H 0.3269 0.0858 0.4080 0.030 Uiso 1 1 calc R . . C16 C 0.21979(11) 0.09827(17) 0.3205(2) 0.0217(5) Uani 1 1 d . . . H16 H 0.2285 0.0921 0.2336 0.026 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 0.0158(3) 0.0167(3) 0.0202(3) -0.0004(2) 0.0025(2) 0.0000(2) N1 0.0167(12) 0.0160(13) 0.0239(16) 0.000 0.0036(11) 0.000 C1 0.0141(14) 0.0177(15) 0.0264(19) 0.000 0.0037(12) 0.000 C2 0.0229(12) 0.0230(12) 0.0291(15) -0.0012(10) -0.0001(10) 0.0013(9) C3 0.0273(13) 0.0245(13) 0.0435(18) -0.0099(12) -0.0001(11) -0.0015(10) C4 0.0256(17) 0.0191(17) 0.058(3) 0.000 0.0022(17) 0.000 C5 0.0169(10) 0.0186(11) 0.0234(13) 0.0000(9) 0.0039(9) 0.0035(9) C6 0.0266(12) 0.0209(12) 0.0253(14) -0.0026(10) 0.0032(10) -0.0012(9) C7 0.0289(13) 0.0244(13) 0.0416(17) 0.0055(11) 0.0095(12) -0.0027(10) C8 0.0289(13) 0.0404(15) 0.0330(17) 0.0143(12) 0.0105(11) 0.0045(11) C9 0.0252(12) 0.0465(16) 0.0207(15) 0.0010(12) 0.0032(10) 0.0029(11) C10 0.0172(11) 0.0279(12) 0.0252(14) -0.0025(10) 0.0020(9) 0.0003(9) C11 0.0185(10) 0.0143(11) 0.0205(13) 0.0008(9) 0.0025(9) 0.0006(8) C12 0.0211(11) 0.0201(12) 0.0275(15) 0.0015(10) 0.0058(9) 0.0025(9) C13 0.0321(13) 0.0235(12) 0.0178(13) 0.0002(10) 0.0033(10) 0.0035(10) C14 0.0250(12) 0.0249(12) 0.0258(15) 0.0012(10) -0.0057(10) 0.0003(10) C15 0.0173(11) 0.0271(12) 0.0307(15) 0.0022(11) 0.0041(9) 0.0013(10) C16 0.0215(11) 0.0223(11) 0.0216(13) 0.0002(10) 0.0047(9) 0.0004(9) _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 N1 1.7315(15) . ? P1 C5 1.834(2) . ? P1 C11 1.841(2) . ? N1 C1 1.455(4) . ? N1 P1 1.7315(15) 2 ? C1 C2 1.391(3) . ? C1 C2 1.391(3) 2 ? C2 C3 1.398(3) . ? C2 H2 0.9500 . ? C3 C4 1.382(3) . ? C3 H3 0.9500 . ? C4 C3 1.382(3) 2 ? C4 H4 0.9500 . ? C5 C10 1.398(3) . ? C5 C6 1.403(3) . ? C6 C7 1.387(3) . ? C6 H6 0.9500 . ? C7 C8 1.386(4) . ? C7 H7 0.9500 . ? C8 C9 1.388(4) . ? C8 H8 0.9500 . ? C9 C10 1.387(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.392(3) . ? C11 C16 1.407(3) . ? C12 C13 1.396(3) . ? C12 H12 0.9500 . ? C13 C14 1.387(3) . ? C13 H13 0.9500 . ? C14 C15 1.382(4) . ? C14 H14 0.9500 . ? C15 C16 1.395(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? 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 C5 102.62(9) . . ? N1 P1 C11 105.56(8) . . ? C5 P1 C11 102.48(10) . . ? C1 N1 P1 123.31(7) . 2 ? C1 N1 P1 123.31(7) . . ? P1 N1 P1 113.37(14) 2 . ? C2 C1 C2 119.3(3) . 2 ? C2 C1 N1 120.34(15) . . ? C2 C1 N1 120.34(15) 2 . ? C1 C2 C3 120.2(2) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 120.1(3) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C3 120.0(3) 2 . ? C3 C4 H4 120.0 2 . ? C3 C4 H4 120.0 . . ? C10 C5 C6 118.4(2) . . ? C10 C5 P1 116.86(17) . . ? C6 C5 P1 124.72(18) . . ? C7 C6 C5 120.7(2) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C8 C7 C6 120.0(2) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 120.1(2) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C10 C9 C8 119.9(2) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C5 120.8(2) . . ? C9 C10 H10 119.6 . . ? C5 C10 H10 119.6 . . ? C12 C11 C16 118.2(2) . . ? C12 C11 P1 121.36(16) . . ? C16 C11 P1 119.61(18) . . ? C11 C12 C13 121.2(2) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C14 C13 C12 119.9(2) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C15 C14 C13 119.9(2) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 120.4(2) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C11 120.5(2) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 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 C5 P1 N1 C1 -35.21(8) . . . . ? C11 P1 N1 C1 71.77(8) . . . . ? C5 P1 N1 P1 144.79(8) . . . 2 ? C11 P1 N1 P1 -108.23(8) . . . 2 ? P1 N1 C1 C2 92.44(11) 2 . . . ? P1 N1 C1 C2 -87.56(11) . . . . ? P1 N1 C1 C2 -87.56(11) 2 . . 2 ? P1 N1 C1 C2 92.44(11) . . . 2 ? C2 C1 C2 C3 -0.44(17) 2 . . . ? N1 C1 C2 C3 179.56(17) . . . . ? C1 C2 C3 C4 0.9(3) . . . . ? C2 C3 C4 C3 -0.44(17) . . . 2 ? N1 P1 C5 C10 -99.82(17) . . . . ? C11 P1 C5 C10 150.85(17) . . . . ? N1 P1 C5 C6 80.27(19) . . . . ? C11 P1 C5 C6 -29.1(2) . . . . ? C10 C5 C6 C7 0.0(3) . . . . ? P1 C5 C6 C7 179.86(18) . . . . ? C5 C6 C7 C8 0.5(4) . . . . ? C6 C7 C8 C9 -0.4(4) . . . . ? C7 C8 C9 C10 -0.2(4) . . . . ? C8 C9 C10 C5 0.7(4) . . . . ? C6 C5 C10 C9 -0.5(3) . . . . ? P1 C5 C10 C9 179.54(18) . . . . ? N1 P1 C11 C12 36.5(2) . . . . ? C5 P1 C11 C12 143.57(18) . . . . ? N1 P1 C11 C16 -154.35(17) . . . . ? C5 P1 C11 C16 -47.26(19) . . . . ? C16 C11 C12 C13 1.3(3) . . . . ? P1 C11 C12 C13 170.58(17) . . . . ? C11 C12 C13 C14 -0.6(3) . . . . ? C12 C13 C14 C15 -0.1(4) . . . . ? C13 C14 C15 C16 0.2(4) . . . . ? C14 C15 C16 C11 0.5(4) . . . . ? C12 C11 C16 C15 -1.2(3) . . . . ? P1 C11 C16 C15 -170.69(17) . . . . ? _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.943 _refine_diff_density_max 0.271 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.046