Supplementary Material (ESI) for Dalton Transactions This journal is (C) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _audit_creation_date 'January 28, 2008' _audit_creation_method 'from SHELXL97 CIF and IUCr SHELXL97-template' _audit_update_record ; compilation of CIF files ; _publ_contact_author_name 'Dr. Nathan D. Jones' _publ_contact_author_address ; Department of Chemistry The University of Western Ontario London, Ontario CANADA N6A 5B7 ; _publ_contact_author_phone '(519) 661-2111 ext. 84456' _publ_contact_author_fax '(519) 661-3022' _publ_contact_author_email njones26@uwo.ca _publ_requested_category ? _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _publ_section_title ; N-Heterocyclic phosphenium cations: Syntheses and cycloaddition reactions ; _publ_section_title_footnote ; ? ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Christine A. Caputo' ; ? ; ; Department of Chemistry The University of Western Ontario London, Ontario, N6A 5B7, CANADA ; 'Jacquelyn T. Price' ; ? ; ; Department of Chemistry The University of Western Ontario London, Ontario, N6A 5B7, CANADA ; 'Michael C. Jennings' ; ? ; ; Department of Chemistry The University of Western Ontario London, Ontario, N6A 5B7, CANADA ; 'Robert McDonald' ; ? ; ; Department of Chemistry The University of Alberta Edmonton, Alberta, T6G 2G2, CANADA ; 'Nathan D. Jones' ; ? ; ; Department of Chemistry The University of Western Ontario London, Ontario, N6A 5B7, CANADA ; data_1a _database_code_depnum_ccdc_archive 'CCDC 676351' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H14 F3 N2 O3 P S' _chemical_formula_weight 390.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F .0171 .0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P .1023 .0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.6619(3) _cell_length_b 19.3867(5) _cell_length_c 8.7282(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.851(2) _cell_angle_gamma 90.00 _cell_volume 1662.52(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 16997 _cell_measurement_theta_min 2.04 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.559 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.340 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8483 _exptl_absorpt_correction_T_max 0.9790 _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa-CCD' _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7349 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.62 _reflns_number_total 3830 _reflns_number_gt 3116 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Nonius, 1997-2001)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 2001)' _computing_publication_material SHELXTL/PC _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^)+(0.0491P)^2^+0.9418P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3830 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0527 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1081 _refine_ls_wR_factor_gt 0.1002 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.57662(5) 0.06771(2) 0.30708(6) 0.02677(13) Uani 1 1 d . . . N1 N 0.64088(16) 0.14526(7) 0.32259(19) 0.0263(3) Uani 1 1 d . . . C1 C 0.5700(2) 0.19297(9) 0.1837(2) 0.0304(4) Uani 1 1 d . . . H3A H 0.6291 0.2046 0.1237 0.036 Uiso 1 1 calc R . . H3B H 0.5455 0.2362 0.2260 0.036 Uiso 1 1 calc R . . C2 C 0.4421(2) 0.15576(9) 0.0684(2) 0.0302(4) Uani 1 1 d . . . H4A H 0.3599 0.1773 0.0741 0.036 Uiso 1 1 calc R . . H4B H 0.4352 0.1579 -0.0479 0.036 Uiso 1 1 calc R . . N2 N 0.45486(16) 0.08309(8) 0.12640(19) 0.0266(3) Uani 1 1 d . . . C11 C 0.35704(11) 0.03208(5) 0.03836(14) 0.0265(4) Uani 1 1 d G . . C12 C 0.35964(12) -0.03174(6) 0.11215(12) 0.0337(4) Uani 1 1 d G . . H12A H 0.4245 -0.0405 0.2212 0.040 Uiso 1 1 calc R . . C13 C 0.26735(14) -0.08267(5) 0.02632(16) 0.0379(5) Uani 1 1 d G . . H13A H 0.2691 -0.1263 0.0768 0.045 Uiso 1 1 calc R . . C14 C 0.17245(12) -0.06980(6) -0.13329(15) 0.0372(5) Uani 1 1 d G . . H14A H 0.1094 -0.1046 -0.1919 0.045 Uiso 1 1 calc R . . C15 C 0.16985(12) -0.00599(7) -0.20708(12) 0.0379(5) Uani 1 1 d G . . H15A H 0.1050 0.0028 -0.3162 0.045 Uiso 1 1 calc R . . C16 C 0.26214(13) 0.04495(5) -0.12126(14) 0.0317(4) Uani 1 1 d G . . H16A H 0.2604 0.0886 -0.1717 0.038 Uiso 1 1 calc R . . C21 C 0.76244(10) 0.16504(6) 0.45732(13) 0.0276(4) Uani 1 1 d G . . C22 C 0.81258(12) 0.12399(5) 0.59884(15) 0.0324(4) Uani 1 1 d G . . H22A H 0.7622 0.0850 0.6087 0.039 Uiso 1 1 calc R . . C23 C 0.93647(13) 0.13992(6) 0.72587(13) 0.0369(5) Uani 1 1 d G . . H23A H 0.9707 0.1119 0.8226 0.044 Uiso 1 1 calc R . . C24 C 1.01022(10) 0.19691(7) 0.71137(14) 0.0386(5) Uani 1 1 d G . . H24A H 1.0949 0.2078 0.7982 0.046 Uiso 1 1 calc R . . C25 C 0.96008(12) 0.23796(6) 0.56986(16) 0.0384(5) Uani 1 1 d G . . H25A H 1.0105 0.2769 0.5600 0.046 Uiso 1 1 calc R . . C26 C 0.83619(13) 0.22203(6) 0.44283(13) 0.0330(4) Uani 1 1 d G . . H26A H 0.8019 0.2501 0.3461 0.040 Uiso 1 1 calc R . . O1 O 0.46420(13) 0.07978(6) 0.46807(16) 0.0293(3) Uani 1 1 d . . . O2 O 0.39803(16) 0.19998(7) 0.40110(18) 0.0364(3) Uani 1 1 d . . . O3 O 0.39960(16) 0.14815(8) 0.65715(17) 0.0388(3) Uani 1 1 d . . . S34 S 0.38654(5) 0.13962(2) 0.48895(6) 0.02701(13) Uani 1 1 d . . . C35 C 0.2110(2) 0.11107(10) 0.3783(3) 0.0331(4) Uani 1 1 d . . . F3 F 0.18708(14) 0.05154(7) 0.43574(19) 0.0533(4) Uani 1 1 d . . . F1 F 0.12496(13) 0.15718(7) 0.39367(18) 0.0502(4) Uani 1 1 d . . . F2 F 0.18274(13) 0.10391(8) 0.21659(16) 0.0505(4) 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 0.0309(3) 0.0217(2) 0.0272(3) 0.00198(18) 0.0107(2) 0.00136(18) N1 0.0310(8) 0.0233(7) 0.0253(8) 0.0035(6) 0.0117(6) 0.0005(6) C1 0.0409(11) 0.0248(9) 0.0275(9) 0.0048(7) 0.0155(8) 0.0000(8) C2 0.0424(11) 0.0233(9) 0.0253(9) 0.0051(7) 0.0136(8) 0.0012(8) N2 0.0353(8) 0.0212(7) 0.0240(8) 0.0019(6) 0.0121(7) 0.0002(6) C11 0.0310(9) 0.0260(9) 0.0256(9) -0.0020(7) 0.0144(8) 0.0005(7) C12 0.0403(11) 0.0298(10) 0.0300(10) 0.0023(8) 0.0126(9) -0.0048(8) C13 0.0435(12) 0.0320(10) 0.0408(12) 0.0003(9) 0.0192(10) -0.0048(9) C14 0.0343(11) 0.0398(11) 0.0398(12) -0.0105(9) 0.0170(9) -0.0076(9) C15 0.0328(10) 0.0463(12) 0.0301(10) -0.0033(9) 0.0073(8) -0.0008(9) C16 0.0366(10) 0.0323(10) 0.0268(9) 0.0026(8) 0.0127(8) 0.0017(8) C21 0.0306(9) 0.0251(9) 0.0296(9) -0.0038(7) 0.0143(8) 0.0021(7) C22 0.0372(10) 0.0277(9) 0.0310(10) 0.0003(8) 0.0118(8) 0.0010(8) C23 0.0401(11) 0.0348(11) 0.0325(10) -0.0022(8) 0.0106(9) 0.0047(9) C24 0.0337(10) 0.0420(11) 0.0388(11) -0.0121(9) 0.0125(9) -0.0003(9) C25 0.0418(11) 0.0375(11) 0.0405(12) -0.0093(9) 0.0208(10) -0.0088(9) C26 0.0390(11) 0.0292(9) 0.0336(10) -0.0024(8) 0.0173(9) -0.0033(8) O1 0.0327(7) 0.0258(6) 0.0310(7) 0.0032(5) 0.0142(6) 0.0037(5) O2 0.0548(9) 0.0233(6) 0.0380(8) 0.0028(6) 0.0256(7) 0.0005(6) O3 0.0514(9) 0.0434(8) 0.0241(7) -0.0042(6) 0.0174(7) -0.0028(7) S34 0.0355(3) 0.0236(2) 0.0235(2) -0.00077(17) 0.01321(19) 0.00014(18) C35 0.0360(10) 0.0306(10) 0.0334(10) 0.0014(8) 0.0142(8) 0.0069(8) F3 0.0425(7) 0.0406(7) 0.0702(10) 0.0108(7) 0.0145(7) -0.0080(6) F1 0.0413(7) 0.0513(8) 0.0594(9) -0.0038(7) 0.0211(7) 0.0160(6) F2 0.0410(7) 0.0713(10) 0.0325(7) -0.0116(6) 0.0068(6) 0.0031(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 N2 1.6344(16) . ? P1 N1 1.6357(15) . ? P1 O1 2.1850(14) . ? N1 C21 1.4233(17) . ? N1 C1 1.478(2) . ? C1 C2 1.525(3) . ? C1 H3A 0.9900 . ? C1 H3B 0.9900 . ? C2 N2 1.485(2) . ? C2 H4A 0.9900 . ? C2 H4B 0.9900 . ? N2 C11 1.4262(17) . ? C11 C12 1.3900 . ? C11 C16 1.3900 . ? C12 C13 1.3900 . ? C12 H12A 0.9500 . ? C13 C14 1.3900 . ? C13 H13A 0.9500 . ? C14 C15 1.3900 . ? C14 H14A 0.9500 . ? C15 C16 1.3900 . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C21 C22 1.3900 . ? C21 C26 1.3900 . ? C22 C23 1.3900 . ? C22 H22A 0.9500 . ? C23 C24 1.3900 . ? C23 H23A 0.9500 . ? C24 C25 1.3900 . ? C24 H24A 0.9500 . ? C25 C26 1.3900 . ? C25 H25A 0.9500 . ? C26 H26A 0.9500 . ? O1 S34 1.4772(13) . ? O2 S34 1.4301(14) . ? O3 S34 1.4294(14) . ? S34 C35 1.827(2) . ? C35 F3 1.322(2) . ? C35 F1 1.325(2) . ? C35 F2 1.331(2) . ? 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 N2 P1 N1 93.58(8) . . ? N2 P1 O1 99.93(7) . . ? N1 P1 O1 99.50(7) . . ? C21 N1 C1 121.37(13) . . ? C21 N1 P1 122.26(11) . . ? C1 N1 P1 116.28(12) . . ? N1 C1 C2 106.66(14) . . ? N1 C1 H3A 110.4 . . ? C2 C1 H3A 110.4 . . ? N1 C1 H3B 110.4 . . ? C2 C1 H3B 110.4 . . ? H3A C1 H3B 108.6 . . ? N2 C2 C1 106.49(15) . . ? N2 C2 H4A 110.4 . . ? C1 C2 H4A 110.4 . . ? N2 C2 H4B 110.4 . . ? C1 C2 H4B 110.4 . . ? H4A C2 H4B 108.6 . . ? C11 N2 C2 121.55(14) . . ? C11 N2 P1 122.28(11) . . ? C2 N2 P1 115.79(12) . . ? C12 C11 C16 120.0 . . ? C12 C11 N2 119.26(9) . . ? C16 C11 N2 120.72(9) . . ? C11 C12 C13 120.0 . . ? C11 C12 H12A 120.0 . . ? C13 C12 H12A 120.0 . . ? C12 C13 C14 120.0 . . ? C12 C13 H13A 120.0 . . ? C14 C13 H13A 120.0 . . ? C13 C14 C15 120.0 . . ? C13 C14 H14A 120.0 . . ? C15 C14 H14A 120.0 . . ? C16 C15 C14 120.0 . . ? C16 C15 H15A 120.0 . . ? C14 C15 H15A 120.0 . . ? C15 C16 C11 120.0 . . ? C15 C16 H16A 120.0 . . ? C11 C16 H16A 120.0 . . ? C22 C21 C26 120.0 . . ? C22 C21 N1 119.50(9) . . ? C26 C21 N1 120.32(10) . . ? C23 C22 C21 120.0 . . ? C23 C22 H22A 120.0 . . ? C21 C22 H22A 120.0 . . ? C24 C23 C22 120.0 . . ? C24 C23 H23A 120.0 . . ? C22 C23 H23A 120.0 . . ? C23 C24 C25 120.0 . . ? C23 C24 H24A 120.0 . . ? C25 C24 H24A 120.0 . . ? C26 C25 C24 120.0 . . ? C26 C25 H25A 120.0 . . ? C24 C25 H25A 120.0 . . ? C25 C26 C21 120.0 . . ? C25 C26 H26A 120.0 . . ? C21 C26 H26A 120.0 . . ? S34 O1 P1 129.58(8) . . ? O3 S34 O2 117.49(9) . . ? O3 S34 O1 112.44(8) . . ? O2 S34 O1 114.06(8) . . ? O3 S34 C35 104.43(9) . . ? O2 S34 C35 104.35(9) . . ? O1 S34 C35 101.83(8) . . ? F3 C35 F1 107.90(17) . . ? F3 C35 F2 108.28(17) . . ? F1 C35 F2 107.31(16) . . ? F3 C35 S34 111.89(14) . . ? F1 C35 S34 110.45(14) . . ? F2 C35 S34 110.85(14) . . ? 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 N2 P1 N1 C21 -176.01(13) . . . . ? O1 P1 N1 C21 83.30(13) . . . . ? N2 P1 N1 C1 0.69(14) . . . . ? O1 P1 N1 C1 -100.01(13) . . . . ? C21 N1 C1 C2 -177.46(14) . . . . ? P1 N1 C1 C2 5.8(2) . . . . ? N1 C1 C2 N2 -10.1(2) . . . . ? C1 C2 N2 C11 -175.22(14) . . . . ? C1 C2 N2 P1 11.7(2) . . . . ? N1 P1 N2 C11 179.40(13) . . . . ? O1 P1 N2 C11 -80.30(13) . . . . ? N1 P1 N2 C2 -7.58(15) . . . . ? O1 P1 N2 C2 92.72(14) . . . . ? C2 N2 C11 C12 -168.71(13) . . . . ? P1 N2 C11 C12 3.92(17) . . . . ? C2 N2 C11 C16 13.0(2) . . . . ? P1 N2 C11 C16 -174.37(9) . . . . ? C16 C11 C12 C13 0.0 . . . . ? N2 C11 C12 C13 -178.30(13) . . . . ? C11 C12 C13 C14 0.0 . . . . ? C12 C13 C14 C15 0.0 . . . . ? C13 C14 C15 C16 0.0 . . . . ? C14 C15 C16 C11 0.0 . . . . ? C12 C11 C16 C15 0.0 . . . . ? N2 C11 C16 C15 178.28(13) . . . . ? C1 N1 C21 C22 168.60(13) . . . . ? P1 N1 C21 C22 -14.87(17) . . . . ? C1 N1 C21 C26 -16.3(2) . . . . ? P1 N1 C21 C26 160.25(9) . . . . ? C26 C21 C22 C23 0.0 . . . . ? N1 C21 C22 C23 175.13(13) . . . . ? C21 C22 C23 C24 0.0 . . . . ? C22 C23 C24 C25 0.0 . . . . ? C23 C24 C25 C26 0.0 . . . . ? C24 C25 C26 C21 0.0 . . . . ? C22 C21 C26 C25 0.0 . . . . ? N1 C21 C26 C25 -175.09(13) . . . . ? N2 P1 O1 S34 -57.55(12) . . . . ? N1 P1 O1 S34 37.82(12) . . . . ? P1 O1 S34 O3 -143.24(10) . . . . ? P1 O1 S34 O2 -6.23(14) . . . . ? P1 O1 S34 C35 105.53(11) . . . . ? O3 S34 C35 F3 -61.73(16) . . . . ? O2 S34 C35 F3 174.36(14) . . . . ? O1 S34 C35 F3 55.44(16) . . . . ? O3 S34 C35 F1 58.48(16) . . . . ? O2 S34 C35 F1 -65.43(16) . . . . ? O1 S34 C35 F1 175.65(13) . . . . ? O3 S34 C35 F2 177.29(13) . . . . ? O2 S34 C35 F2 53.38(15) . . . . ? O1 S34 C35 F2 -65.54(15) . . . . ? _diffrn_measured_fraction_theta_max .992 _diffrn_reflns_theta_full 27.62 _diffrn_measured_fraction_theta_full .992 _refine_diff_density_max .428 _refine_diff_density_min -.371 _refine_diff_density_rms .055 data_3b _database_code_depnum_ccdc_archive 'CCDC 676352' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 Cl N2 O2 P' _chemical_formula_sum 'C16 H18 Cl N2 O2 P' _chemical_formula_weight 336.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.9575(6) _cell_length_b 6.3256(4) _cell_length_c 28.149(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.7496(10) _cell_angle_gamma 90.00 _cell_volume 1580.39(18) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 6620 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 27.37 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.351 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8989 _exptl_absorpt_correction_T_max 0.9395 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13207 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.46 _reflns_number_total 3577 _reflns_number_gt 3022 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'DIRDIF-96 (Beurskens et al., 1996)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1997)' _computing_publication_material 'Bruker SHELXTL (Bruker, 1997)' _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^)+(0.0428P)^2^+0.5756P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3577 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0910 _refine_ls_wR_factor_gt 0.0867 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 Cl Cl -0.13668(5) 0.39872(6) 0.140016(15) 0.04321(13) Uani 1 1 d . . . P P 0.00827(5) 0.28876(6) 0.087882(14) 0.03128(11) Uani 1 1 d . . . O1 O -0.54161(14) 0.23858(19) -0.09415(4) 0.0440(3) Uani 1 1 d . . . O2 O 0.57972(13) 0.39533(18) 0.26118(4) 0.0405(3) Uani 1 1 d . . . N1 N -0.09138(15) 0.09201(19) 0.05976(5) 0.0320(3) Uani 1 1 d . . . N2 N 0.12089(14) 0.11836(19) 0.12074(5) 0.0319(3) Uani 1 1 d . . . C1 C -0.04699(18) -0.1226(2) 0.07672(6) 0.0330(3) Uani 1 1 d . . . H1A H 0.0097 -0.1950 0.0536 0.040 Uiso 1 1 calc R . . H1B H -0.1369 -0.2082 0.0808 0.040 Uiso 1 1 calc R . . C2 C 0.05163(18) -0.0913(2) 0.12445(6) 0.0345(3) Uani 1 1 d . . . H2A H -0.0096 -0.0946 0.1512 0.041 Uiso 1 1 calc R . . H2B H 0.1298 -0.2026 0.1297 0.041 Uiso 1 1 calc R . . C11 C -0.20565(17) 0.1226(2) 0.02052(5) 0.0300(3) Uani 1 1 d . . . C12 C -0.26516(19) 0.3246(2) 0.01004(6) 0.0368(4) Uani 1 1 d . . . H12 H -0.2299 0.4407 0.0298 0.044 Uiso 1 1 calc R . . C13 C -0.3745(2) 0.3566(3) -0.02869(6) 0.0383(4) Uani 1 1 d . . . H13 H -0.4120 0.4952 -0.0357 0.046 Uiso 1 1 calc R . . C14 C -0.43035(18) 0.1889(3) -0.05751(5) 0.0337(3) Uani 1 1 d . . . C15 C -0.37408(18) -0.0122(2) -0.04694(6) 0.0346(3) Uani 1 1 d . . . H15 H -0.4122 -0.1287 -0.0662 0.041 Uiso 1 1 calc R . . C16 C -0.26245(18) -0.0443(2) -0.00847(6) 0.0336(3) Uani 1 1 d . . . H16 H -0.2242 -0.1827 -0.0018 0.040 Uiso 1 1 calc R . . C17 C -0.6022(2) 0.0716(3) -0.12465(6) 0.0431(4) Uani 1 1 d . . . H17A H -0.6815 0.1274 -0.1488 0.052 Uiso 1 1 calc R . . H17B H -0.6448 -0.0368 -0.1055 0.052 Uiso 1 1 calc R . . H17C H -0.5222 0.0091 -0.1406 0.052 Uiso 1 1 calc R . . C21 C 0.23688(17) 0.1898(2) 0.15649(5) 0.0308(3) Uani 1 1 d . . . C22 C 0.31790(18) 0.3712(2) 0.14850(6) 0.0343(3) Uani 1 1 d . . . H22 H 0.2941 0.4463 0.1192 0.041 Uiso 1 1 calc R . . C23 C 0.43275(19) 0.4441(3) 0.18253(6) 0.0364(4) Uani 1 1 d . . . H23 H 0.4863 0.5689 0.1766 0.044 Uiso 1 1 calc R . . C24 C 0.46929(17) 0.3346(3) 0.22515(5) 0.0328(3) Uani 1 1 d . . . C25 C 0.39076(19) 0.1514(3) 0.23316(6) 0.0361(4) Uani 1 1 d . . . H25 H 0.4166 0.0745 0.2621 0.043 Uiso 1 1 calc R . . C26 C 0.27513(18) 0.0801(3) 0.19934(6) 0.0354(4) Uani 1 1 d . . . H26 H 0.2215 -0.0445 0.2054 0.042 Uiso 1 1 calc R . . C27 C 0.6641(2) 0.5802(3) 0.25262(6) 0.0453(4) Uani 1 1 d . . . H27A H 0.7403 0.6069 0.2804 0.054 Uiso 1 1 calc R . . H27B H 0.5960 0.7018 0.2476 0.054 Uiso 1 1 calc R . . H27C H 0.7138 0.5587 0.2240 0.054 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 Cl 0.0549(3) 0.0328(2) 0.0441(2) -0.00269(17) 0.01454(19) 0.00694(17) P 0.0380(2) 0.02208(19) 0.0343(2) 0.00348(15) 0.00699(16) -0.00184(15) O1 0.0530(7) 0.0373(7) 0.0391(6) 0.0025(5) -0.0027(5) 0.0013(5) O2 0.0463(7) 0.0400(7) 0.0345(6) 0.0012(5) 0.0030(5) -0.0027(5) N1 0.0407(7) 0.0204(6) 0.0351(7) 0.0008(5) 0.0058(6) 0.0006(5) N2 0.0351(7) 0.0238(6) 0.0375(7) 0.0041(5) 0.0078(5) -0.0005(5) C1 0.0411(8) 0.0196(7) 0.0392(8) 0.0013(6) 0.0089(7) 0.0020(6) C2 0.0397(8) 0.0214(7) 0.0430(9) 0.0050(6) 0.0084(7) 0.0011(6) C11 0.0362(8) 0.0259(7) 0.0297(7) 0.0005(6) 0.0116(6) -0.0005(6) C12 0.0514(10) 0.0230(7) 0.0356(8) -0.0018(6) 0.0047(7) -0.0002(7) C13 0.0522(10) 0.0246(8) 0.0386(9) 0.0032(6) 0.0070(7) 0.0047(7) C14 0.0396(8) 0.0323(8) 0.0306(8) 0.0030(6) 0.0098(6) -0.0007(7) C15 0.0441(9) 0.0272(8) 0.0336(8) -0.0028(6) 0.0097(7) -0.0030(6) C16 0.0428(9) 0.0228(7) 0.0368(8) -0.0006(6) 0.0113(7) 0.0018(6) C17 0.0414(9) 0.0485(10) 0.0393(9) -0.0033(8) 0.0052(7) -0.0028(8) C21 0.0325(8) 0.0273(7) 0.0340(8) 0.0011(6) 0.0099(6) 0.0028(6) C22 0.0412(9) 0.0295(8) 0.0329(8) 0.0065(6) 0.0070(6) -0.0001(6) C23 0.0420(9) 0.0291(8) 0.0391(9) 0.0025(6) 0.0093(7) -0.0037(7) C24 0.0349(8) 0.0330(8) 0.0317(8) -0.0016(6) 0.0086(6) 0.0031(6) C25 0.0431(9) 0.0340(8) 0.0328(8) 0.0065(6) 0.0110(7) 0.0048(7) C26 0.0389(8) 0.0301(8) 0.0393(9) 0.0067(6) 0.0131(7) -0.0012(6) C27 0.0536(11) 0.0393(10) 0.0408(10) -0.0036(7) -0.0012(8) -0.0076(8) _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 Cl P 2.1993(6) . ? P N1 1.6678(13) . ? P N2 1.6684(13) . ? O1 C14 1.3706(19) . ? O1 C17 1.422(2) . ? O2 C24 1.3726(19) . ? O2 C27 1.431(2) . ? N1 C11 1.4143(19) . ? N1 C1 1.4758(18) . ? N2 C21 1.419(2) . ? N2 C2 1.4735(18) . ? C1 C2 1.518(2) . ? C11 C16 1.388(2) . ? C11 C12 1.400(2) . ? C12 C13 1.379(2) . ? C13 C14 1.387(2) . ? C14 C15 1.386(2) . ? C15 C16 1.386(2) . ? C21 C22 1.392(2) . ? C21 C26 1.394(2) . ? C22 C23 1.387(2) . ? C23 C24 1.386(2) . ? C24 C25 1.390(2) . ? C25 C26 1.384(2) . ? 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 P N2 91.49(6) . . ? N1 P Cl 103.09(5) . . ? N2 P Cl 101.63(5) . . ? C14 O1 C17 117.63(13) . . ? C24 O2 C27 116.68(13) . . ? C11 N1 C1 120.90(12) . . ? C11 N1 P 123.59(10) . . ? C1 N1 P 115.42(10) . . ? C21 N2 C2 120.75(12) . . ? C21 N2 P 121.17(10) . . ? C2 N2 P 113.06(10) . . ? N1 C1 C2 105.38(12) . . ? N2 C2 C1 104.79(12) . . ? C16 C11 C12 118.09(14) . . ? C16 C11 N1 121.62(14) . . ? C12 C11 N1 120.28(14) . . ? C13 C12 C11 120.68(15) . . ? C12 C13 C14 120.79(15) . . ? O1 C14 C15 125.35(15) . . ? O1 C14 C13 115.66(14) . . ? C15 C14 C13 118.97(15) . . ? C14 C15 C16 120.34(15) . . ? C15 C16 C11 121.10(14) . . ? C22 C21 C26 118.54(15) . . ? C22 C21 N2 119.70(13) . . ? C26 C21 N2 121.74(14) . . ? C23 C22 C21 121.12(14) . . ? C24 C23 C22 119.89(15) . . ? O2 C24 C23 124.21(15) . . ? O2 C24 C25 116.33(14) . . ? C23 C24 C25 119.46(15) . . ? C26 C25 C24 120.55(15) . . ? C25 C26 C21 120.44(15) . . ? 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 N2 P N1 C11 -173.19(12) . . . . ? Cl P N1 C11 84.51(12) . . . . ? N2 P N1 C1 3.45(11) . . . . ? Cl P N1 C1 -98.86(11) . . . . ? N1 P N2 C21 -177.29(12) . . . . ? Cl P N2 C21 -73.61(11) . . . . ? N1 P N2 C2 -22.22(11) . . . . ? Cl P N2 C2 81.47(11) . . . . ? C11 N1 C1 C2 -168.43(13) . . . . ? P N1 C1 C2 14.83(16) . . . . ? C21 N2 C2 C1 -171.38(12) . . . . ? P N2 C2 C1 33.43(15) . . . . ? N1 C1 C2 N2 -28.31(16) . . . . ? C1 N1 C11 C16 -11.0(2) . . . . ? P N1 C11 C16 165.46(12) . . . . ? C1 N1 C11 C12 168.75(14) . . . . ? P N1 C11 C12 -14.8(2) . . . . ? C16 C11 C12 C13 -1.5(2) . . . . ? N1 C11 C12 C13 178.72(14) . . . . ? C11 C12 C13 C14 1.4(3) . . . . ? C17 O1 C14 C15 -1.6(2) . . . . ? C17 O1 C14 C13 179.95(14) . . . . ? C12 C13 C14 O1 178.25(15) . . . . ? C12 C13 C14 C15 -0.3(2) . . . . ? O1 C14 C15 C16 -179.14(14) . . . . ? C13 C14 C15 C16 -0.7(2) . . . . ? C14 C15 C16 C11 0.6(2) . . . . ? C12 C11 C16 C15 0.5(2) . . . . ? N1 C11 C16 C15 -179.76(14) . . . . ? C2 N2 C21 C22 169.26(14) . . . . ? P N2 C21 C22 -37.56(18) . . . . ? C2 N2 C21 C26 -9.1(2) . . . . ? P N2 C21 C26 144.04(13) . . . . ? C26 C21 C22 C23 -1.0(2) . . . . ? N2 C21 C22 C23 -179.45(14) . . . . ? C21 C22 C23 C24 0.6(2) . . . . ? C27 O2 C24 C23 -2.1(2) . . . . ? C27 O2 C24 C25 178.20(14) . . . . ? C22 C23 C24 O2 -179.23(14) . . . . ? C22 C23 C24 C25 0.4(2) . . . . ? O2 C24 C25 C26 178.59(14) . . . . ? C23 C24 C25 C26 -1.1(2) . . . . ? C24 C25 C26 C21 0.7(2) . . . . ? C22 C21 C26 C25 0.3(2) . . . . ? N2 C21 C26 C25 178.75(14) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.363 _refine_diff_density_min -0.138 _refine_diff_density_rms 0.056 data_4 _database_code_depnum_ccdc_archive 'CCDC 676353' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H45 Cl11 N2' _chemical_formula_weight 811.62 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' Cl Cl 0.1484 0.1585 '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)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.0405(6) _cell_length_b 12.2573(3) _cell_length_c 21.8456(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.1020(10) _cell_angle_gamma 90.00 _cell_volume 4027.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 21533 _cell_measurement_theta_min 2.04 _cell_measurement_theta_max 25.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.781 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6963 _exptl_absorpt_correction_T_max 0.7855 _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa-CCD' _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13161 _diffrn_reflns_av_R_equivalents 0.0397 _diffrn_reflns_av_sigmaI/netI 0.0599 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 25.03 _reflns_number_total 7018 _reflns_number_gt 5133 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1997-2001)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 2001)' _computing_publication_material SHELXTL/PC _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^)+(0.0876P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7018 _refine_ls_number_parameters 364 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0825 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1466 _refine_ls_wR_factor_gt 0.1307 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.004 _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 Cl1 Cl 0.93501(8) 0.27671(7) 1.09734(5) 0.0333(3) Uani 1 1 d . . . Cl2 Cl 0.94770(8) 0.25530(7) 0.90987(5) 0.0328(3) Uani 1 1 d . . . C11 C 0.9860(3) 0.0407(3) 1.02463(18) 0.0262(9) Uani 1 1 d . . . H11A H 0.9831 0.0035 1.0648 0.039 Uiso 1 1 calc R . . H11B H 1.0306 0.0999 1.0275 0.039 Uiso 1 1 calc R . . N12 N 0.8971(2) 0.0877(2) 1.00911(15) 0.0236(7) Uani 1 1 d . . . H12A H 0.8843 0.1419 1.0369 0.035 Uiso 1 1 calc R . . H12B H 0.9006 0.1196 0.9711 0.035 Uiso 1 1 calc R . . C13 C 0.82362(14) 0.01001(17) 1.00870(12) 0.0240(9) Uani 1 1 d G . . C14 C 0.78755(17) -0.0227(2) 1.06429(9) 0.0282(10) Uani 1 1 d G . . C15 C 0.71927(17) -0.0991(2) 1.06547(10) 0.0367(11) Uani 1 1 d G . . H15A H 0.6946 -0.1214 1.1035 0.044 Uiso 1 1 calc R . . C16 C 0.68704(15) -0.14275(19) 1.01106(13) 0.0410(12) Uani 1 1 d G . . H16A H 0.6404 -0.1949 1.0119 0.049 Uiso 1 1 calc R . . C17 C 0.72310(18) -0.1100(2) 0.95547(10) 0.0357(11) Uani 1 1 d G . . H17A H 0.7011 -0.1399 0.9183 0.043 Uiso 1 1 calc R . . C18 C 0.79139(17) -0.0337(2) 0.95429(9) 0.0286(10) Uani 1 1 d G . . C19 C 0.8187(3) 0.0226(3) 1.12614(19) 0.0315(10) Uani 1 1 d . . . H19A H 0.8693 0.0737 1.1183 0.038 Uiso 1 1 calc R . . C20 C 0.7446(3) 0.0871(4) 1.1579(2) 0.0411(11) Uani 1 1 d . . . H20A H 0.7256 0.1473 1.1315 0.062 Uiso 1 1 calc R . . H20B H 0.7668 0.1164 1.1968 0.062 Uiso 1 1 calc R . . H20C H 0.6940 0.0387 1.1658 0.062 Uiso 1 1 calc R . . C21 C 0.8526(3) -0.0688(4) 1.1687(2) 0.0419(12) Uani 1 1 d . . . H21A H 0.8030 -0.1168 1.1796 0.063 Uiso 1 1 calc R . . H21B H 0.8778 -0.0365 1.2059 0.063 Uiso 1 1 calc R . . H21C H 0.8985 -0.1112 1.1475 0.063 Uiso 1 1 calc R . . C22 C 0.8258(3) 0.0010(3) 0.89038(19) 0.0307(10) Uani 1 1 d . . . H22A H 0.8794 0.0480 0.8965 0.037 Uiso 1 1 calc R . . C23 C 0.7549(4) 0.0692(4) 0.8566(2) 0.0442(12) Uani 1 1 d . . . H23A H 0.7784 0.0926 0.8169 0.066 Uiso 1 1 calc R . . H23B H 0.7398 0.1334 0.8812 0.066 Uiso 1 1 calc R . . H23C H 0.7015 0.0248 0.8502 0.066 Uiso 1 1 calc R . . C24 C 0.8535(3) -0.0983(4) 0.8520(2) 0.0420(12) Uani 1 1 d . . . H24A H 0.8981 -0.1408 0.8745 0.063 Uiso 1 1 calc R . . H24B H 0.8788 -0.0734 0.8131 0.063 Uiso 1 1 calc R . . H24C H 0.8013 -0.1440 0.8439 0.063 Uiso 1 1 calc R . . C31 C 0.9558(2) 0.5279(3) 0.9973(2) 0.0276(9) Uani 1 1 d . . . H31A H 0.9533 0.5703 0.9588 0.041 Uiso 1 1 calc R . . H31B H 0.9480 0.5791 1.0320 0.041 Uiso 1 1 calc R . . N32 N 0.88256(19) 0.4444(2) 0.99790(16) 0.0247(7) Uani 1 1 d . . . H32A H 0.8897 0.3986 0.9649 0.037 Uiso 1 1 calc R . . H32B H 0.8876 0.4030 1.0329 0.037 Uiso 1 1 calc R . . C33 C 0.79454(13) 0.49128(19) 0.99552(13) 0.0261(9) Uani 1 1 d G . . C34 C 0.75072(18) 0.5173(2) 1.04955(11) 0.0342(10) Uani 1 1 d G . . C35 C 0.66446(18) 0.5578(2) 1.04761(12) 0.0418(12) Uani 1 1 d G . . H35A H 0.6345 0.5756 1.0845 0.050 Uiso 1 1 calc R . . C36 C 0.62202(13) 0.5724(2) 0.99164(15) 0.0466(13) Uani 1 1 d G . . H36A H 0.5631 0.6001 0.9903 0.056 Uiso 1 1 calc R . . C37 C 0.66584(18) 0.5464(2) 0.93760(12) 0.0414(12) Uani 1 1 d G . . H37A H 0.6368 0.5564 0.8993 0.050 Uiso 1 1 calc R . . C38 C 0.75210(18) 0.5059(2) 0.93954(11) 0.0339(11) Uani 1 1 d G . . C39 C 0.7954(3) 0.5116(3) 1.1131(2) 0.0390(11) Uani 1 1 d . . . H39A H 0.8547 0.4758 1.1078 0.047 Uiso 1 1 calc R . . C40 C 0.8115(4) 0.6258(4) 1.1395(2) 0.0533(14) Uani 1 1 d . . . H40A H 0.8444 0.6698 1.1097 0.080 Uiso 1 1 calc R . . H40B H 0.8461 0.6199 1.1774 0.080 Uiso 1 1 calc R . . H40C H 0.7542 0.6606 1.1482 0.080 Uiso 1 1 calc R . . C41 C 0.7420(4) 0.4433(4) 1.1584(2) 0.0572(14) Uani 1 1 d . . . H41A H 0.6861 0.4806 1.1679 0.086 Uiso 1 1 calc R . . H41B H 0.7765 0.4336 1.1962 0.086 Uiso 1 1 calc R . . H41C H 0.7292 0.3717 1.1404 0.086 Uiso 1 1 calc R . . C42 C 0.7980(3) 0.4834(3) 0.8779(2) 0.0411(12) Uani 1 1 d . . . H42A H 0.8573 0.4500 0.8867 0.049 Uiso 1 1 calc R . . C43 C 0.8133(4) 0.5870(4) 0.8408(3) 0.0595(15) Uani 1 1 d . . . H43A H 0.7562 0.6231 0.8332 0.089 Uiso 1 1 calc R . . H43B H 0.8411 0.5682 0.8017 0.089 Uiso 1 1 calc R . . H43C H 0.8524 0.6363 0.8637 0.089 Uiso 1 1 calc R . . C44 C 0.7432(4) 0.4004(4) 0.8398(2) 0.0570(15) Uani 1 1 d . . . H44A H 0.6848 0.4315 0.8304 0.086 Uiso 1 1 calc R . . H44B H 0.7357 0.3330 0.8634 0.086 Uiso 1 1 calc R . . H44C H 0.7747 0.3842 0.8016 0.086 Uiso 1 1 calc R . . C70 C 0.4744(3) 0.1953(4) 0.7520(2) 0.0457(12) Uani 1 1 d D . . H70A H 0.4716 0.2065 0.7067 0.055 Uiso 1 1 calc R . . Cl71 Cl 0.57370(10) 0.25041(11) 0.77972(7) 0.0658(4) Uani 1 1 d D . . Cl72 Cl 0.47279(12) 0.05418(12) 0.76765(9) 0.0814(5) Uani 1 1 d D . . Cl73 Cl 0.38233(13) 0.25617(15) 0.78547(9) 0.0901(6) Uani 1 1 d D . . C80 C 0.9694(3) 0.2214(4) 0.7434(2) 0.0513(13) Uani 1 1 d D . . H80A H 0.9639 0.2314 0.7886 0.062 Uiso 1 1 calc R . . Cl81 Cl 1.07470(9) 0.26305(10) 0.72049(7) 0.0535(4) Uani 1 1 d D . . Cl82 Cl 0.95472(12) 0.08277(12) 0.72566(8) 0.0833(5) Uani 1 1 d D . . Cl83 Cl 0.88732(11) 0.29907(14) 0.70669(8) 0.0797(5) Uani 1 1 d D . . C90 C 0.6012(3) 0.1492(4) 1.0013(2) 0.0454(11) Uani 1 1 d D . . H90A H 0.6330 0.0775 1.0001 0.054 Uiso 1 1 calc R . . Cl91 Cl 0.53123(11) 0.14872(18) 1.06378(7) 0.0938(6) Uani 1 1 d D . . Cl92 Cl 0.54159(12) 0.1630(2) 0.93369(8) 0.1120(8) Uani 1 1 d D . . Cl93 Cl 0.68094(12) 0.25214(11) 1.00699(9) 0.0836(5) Uani 1 1 d 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 Cl1 0.0461(7) 0.0260(5) 0.0277(6) 0.0004(4) -0.0051(5) -0.0001(4) Cl2 0.0420(6) 0.0279(5) 0.0286(6) -0.0025(4) 0.0032(5) -0.0036(4) C11 0.021(2) 0.028(2) 0.029(2) -0.0061(16) -0.0029(18) -0.0008(16) N12 0.0217(16) 0.0208(16) 0.028(2) -0.0004(14) 0.0007(15) -0.0002(12) C13 0.020(2) 0.0220(19) 0.030(2) 0.0001(16) -0.0022(19) -0.0002(15) C14 0.023(2) 0.027(2) 0.035(3) 0.0028(18) -0.006(2) 0.0012(16) C15 0.032(3) 0.038(2) 0.040(3) 0.014(2) -0.002(2) -0.0048(19) C16 0.034(3) 0.038(2) 0.051(3) 0.008(2) -0.007(2) -0.0126(19) C17 0.030(3) 0.036(2) 0.041(3) -0.003(2) -0.012(2) -0.0038(19) C18 0.025(2) 0.026(2) 0.034(3) -0.0007(18) -0.006(2) 0.0037(17) C19 0.033(3) 0.036(2) 0.026(2) 0.0053(18) 0.007(2) 0.0025(19) C20 0.034(3) 0.051(3) 0.038(3) -0.005(2) 0.004(2) 0.010(2) C21 0.049(3) 0.046(3) 0.030(3) 0.003(2) -0.007(2) 0.007(2) C22 0.029(2) 0.035(2) 0.028(3) -0.0106(18) -0.005(2) 0.0005(18) C23 0.052(3) 0.045(3) 0.035(3) 0.003(2) -0.005(3) 0.005(2) C24 0.044(3) 0.042(3) 0.040(3) -0.011(2) -0.001(2) 0.001(2) C31 0.022(2) 0.0247(19) 0.037(2) -0.0013(18) 0.001(2) -0.0043(15) N32 0.0226(17) 0.0233(15) 0.0283(18) 0.0012(15) -0.0033(17) -0.0029(13) C33 0.023(2) 0.0204(19) 0.035(3) -0.0014(18) -0.005(2) -0.0018(15) C34 0.028(2) 0.029(2) 0.046(3) -0.0024(19) 0.000(2) -0.0022(18) C35 0.035(3) 0.038(2) 0.052(3) -0.007(2) 0.005(2) 0.002(2) C36 0.028(2) 0.043(3) 0.069(4) -0.005(3) -0.010(3) 0.0023(19) C37 0.031(3) 0.045(2) 0.048(3) -0.005(2) -0.016(2) 0.000(2) C38 0.034(3) 0.028(2) 0.039(3) -0.0007(18) -0.009(2) -0.0036(19) C39 0.040(3) 0.043(3) 0.034(3) -0.002(2) 0.005(2) 0.005(2) C40 0.056(4) 0.050(3) 0.055(4) -0.020(2) -0.003(3) 0.003(3) C41 0.055(4) 0.069(3) 0.048(3) 0.004(3) 0.008(3) 0.002(3) C42 0.036(3) 0.043(3) 0.044(3) 0.006(2) -0.014(2) -0.001(2) C43 0.052(3) 0.064(3) 0.062(4) 0.024(3) -0.004(3) -0.009(3) C44 0.066(4) 0.053(3) 0.052(4) -0.010(3) -0.017(3) 0.001(3) C70 0.045(3) 0.056(3) 0.036(3) 0.002(2) -0.005(2) 0.001(2) Cl71 0.0693(11) 0.0772(10) 0.0509(9) 0.0050(7) -0.0067(8) -0.0255(7) Cl72 0.0813(11) 0.0538(8) 0.1090(13) 0.0077(8) 0.0052(10) -0.0153(7) Cl73 0.0806(13) 0.1114(14) 0.0783(13) -0.0012(10) 0.0141(10) 0.0323(10) C80 0.047(3) 0.073(3) 0.034(3) 0.006(2) -0.012(2) -0.016(3) Cl81 0.0454(8) 0.0602(7) 0.0550(9) 0.0131(6) -0.0037(7) -0.0099(6) Cl82 0.0871(12) 0.0703(9) 0.0924(12) 0.0173(8) -0.0400(10) -0.0331(8) Cl83 0.0550(9) 0.1087(12) 0.0754(12) 0.0023(9) -0.0149(8) 0.0201(9) C90 0.043(3) 0.048(3) 0.046(3) 0.002(2) -0.007(3) 0.001(2) Cl91 0.0479(9) 0.1919(19) 0.0416(9) 0.0206(10) -0.0012(8) 0.0050(10) Cl92 0.0543(10) 0.242(2) 0.0392(9) -0.0073(12) -0.0065(8) 0.0103(13) Cl93 0.0918(12) 0.0514(8) 0.1075(14) 0.0023(8) -0.0065(12) -0.0237(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C11 N12 1.495(5) . ? C11 C11 1.527(7) 3_757 ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? N12 C13 1.458(3) . ? N12 H12A 0.9200 . ? N12 H12B 0.9200 . ? C13 C14 1.3900 . ? C13 C18 1.3900 . ? C14 C15 1.3900 . ? C14 C19 1.533(5) . ? C15 C16 1.3900 . ? C15 H15A 0.9500 . ? C16 C17 1.3900 . ? C16 H16A 0.9500 . ? C17 C18 1.3900 . ? C17 H17A 0.9500 . ? C18 C22 1.549(5) . ? C19 C20 1.534(6) . ? C19 C21 1.541(6) . ? C19 H19A 1.0000 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C24 1.536(6) . ? C22 C23 1.541(6) . ? C22 H22A 1.0000 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C31 C31 1.498(7) 3_767 ? C31 N32 1.504(4) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? N32 C33 1.444(3) . ? N32 H32A 0.9200 . ? N32 H32B 0.9200 . ? C33 C34 1.3900 . ? C33 C38 1.3900 . ? C34 C35 1.3900 . ? C34 C39 1.543(5) . ? C35 C36 1.3900 . ? C35 H35A 0.9500 . ? C36 C37 1.3900 . ? C36 H36A 0.9500 . ? C37 C38 1.3900 . ? C37 H37A 0.9500 . ? C38 C42 1.539(6) . ? C39 C41 1.527(7) . ? C39 C40 1.532(6) . ? C39 H39A 1.0000 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C42 C43 1.524(6) . ? C42 C44 1.551(7) . ? C42 H42A 1.0000 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C70 Cl73 1.736(5) . ? C70 Cl71 1.746(5) . ? C70 Cl72 1.764(5) . ? C70 H70A 1.0000 . ? C80 Cl81 1.738(5) . ? C80 Cl83 1.752(5) . ? C80 Cl82 1.757(5) . ? C80 H80A 1.0000 . ? C90 Cl91 1.725(5) . ? C90 Cl92 1.735(5) . ? C90 Cl93 1.745(4) . ? C90 H90A 1.0000 . ? 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 N12 C11 C11 109.8(4) . 3_757 ? N12 C11 H11A 109.7 . . ? C11 C11 H11A 109.7 3_757 . ? N12 C11 H11B 109.7 . . ? C11 C11 H11B 109.7 3_757 . ? H11A C11 H11B 108.2 . . ? C13 N12 C11 115.3(2) . . ? C13 N12 H12A 108.4 . . ? C11 N12 H12A 108.4 . . ? C13 N12 H12B 108.4 . . ? C11 N12 H12B 108.4 . . ? H12A N12 H12B 107.5 . . ? C14 C13 C18 120.0 . . ? C14 C13 N12 118.7(2) . . ? C18 C13 N12 121.3(2) . . ? C13 C14 C15 120.0 . . ? C13 C14 C19 123.1(2) . . ? C15 C14 C19 116.9(2) . . ? C14 C15 C16 120.0 . . ? C14 C15 H15A 120.0 . . ? C16 C15 H15A 120.0 . . ? C17 C16 C15 120.0 . . ? C17 C16 H16A 120.0 . . ? C15 C16 H16A 120.0 . . ? C16 C17 C18 120.0 . . ? C16 C17 H17A 120.0 . . ? C18 C17 H17A 120.0 . . ? C17 C18 C13 120.0 . . ? C17 C18 C22 116.7(2) . . ? C13 C18 C22 123.3(2) . . ? C14 C19 C20 111.3(3) . . ? C14 C19 C21 111.6(3) . . ? C20 C19 C21 110.0(4) . . ? C14 C19 H19A 107.9 . . ? C20 C19 H19A 107.9 . . ? C21 C19 H19A 107.9 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C24 C22 C23 110.9(4) . . ? C24 C22 C18 111.5(3) . . ? C23 C22 C18 110.4(3) . . ? C24 C22 H22A 108.0 . . ? C23 C22 H22A 108.0 . . ? C18 C22 H22A 108.0 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C31 C31 N32 109.8(3) 3_767 . ? C31 C31 H31A 109.7 3_767 . ? N32 C31 H31A 109.7 . . ? C31 C31 H31B 109.7 3_767 . ? N32 C31 H31B 109.7 . . ? H31A C31 H31B 108.2 . . ? C33 N32 C31 113.6(2) . . ? C33 N32 H32A 108.8 . . ? C31 N32 H32A 108.8 . . ? C33 N32 H32B 108.8 . . ? C31 N32 H32B 108.8 . . ? H32A N32 H32B 107.7 . . ? C34 C33 C38 120.0 . . ? C34 C33 N32 119.8(2) . . ? C38 C33 N32 120.2(2) . . ? C35 C34 C33 120.0 . . ? C35 C34 C39 116.7(3) . . ? C33 C34 C39 123.2(3) . . ? C34 C35 C36 120.0 . . ? C34 C35 H35A 120.0 . . ? C36 C35 H35A 120.0 . . ? C37 C36 C35 120.0 . . ? C37 C36 H36A 120.0 . . ? C35 C36 H36A 120.0 . . ? C36 C37 C38 120.0 . . ? C36 C37 H37A 120.0 . . ? C38 C37 H37A 120.0 . . ? C37 C38 C33 120.0 . . ? C37 C38 C42 117.2(2) . . ? C33 C38 C42 122.7(2) . . ? C41 C39 C40 109.8(4) . . ? C41 C39 C34 112.3(4) . . ? C40 C39 C34 111.4(4) . . ? C41 C39 H39A 107.7 . . ? C40 C39 H39A 107.7 . . ? C34 C39 H39A 107.7 . . ? C39 C40 H40A 109.5 . . ? C39 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C39 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C39 C41 H41A 109.5 . . ? C39 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C39 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C43 C42 C38 112.6(4) . . ? C43 C42 C44 110.0(4) . . ? C38 C42 C44 110.4(4) . . ? C43 C42 H42A 107.9 . . ? C38 C42 H42A 107.9 . . ? C44 C42 H42A 107.9 . . ? C42 C43 H43A 109.5 . . ? C42 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C42 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C42 C44 H44A 109.5 . . ? C42 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C42 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? Cl73 C70 Cl71 111.7(3) . . ? Cl73 C70 Cl72 109.2(3) . . ? Cl71 C70 Cl72 108.9(2) . . ? Cl73 C70 H70A 109.0 . . ? Cl71 C70 H70A 109.0 . . ? Cl72 C70 H70A 109.0 . . ? Cl81 C80 Cl83 110.5(3) . . ? Cl81 C80 Cl82 109.6(3) . . ? Cl83 C80 Cl82 109.7(3) . . ? Cl81 C80 H80A 109.0 . . ? Cl83 C80 H80A 109.0 . . ? Cl82 C80 H80A 109.0 . . ? Cl91 C90 Cl92 111.0(2) . . ? Cl91 C90 Cl93 111.5(3) . . ? Cl92 C90 Cl93 110.1(3) . . ? Cl91 C90 H90A 108.0 . . ? Cl92 C90 H90A 108.0 . . ? Cl93 C90 H90A 108.0 . . ? 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 C11 C11 N12 C13 64.5(5) 3_757 . . . ? C11 N12 C13 C14 78.1(3) . . . . ? C11 N12 C13 C18 -100.0(3) . . . . ? C18 C13 C14 C15 0.0 . . . . ? N12 C13 C14 C15 -178.1(2) . . . . ? C18 C13 C14 C19 -179.3(3) . . . . ? N12 C13 C14 C19 2.6(3) . . . . ? C13 C14 C15 C16 0.0 . . . . ? C19 C14 C15 C16 179.3(3) . . . . ? C14 C15 C16 C17 0.0 . . . . ? C15 C16 C17 C18 0.0 . . . . ? C16 C17 C18 C13 0.0 . . . . ? C16 C17 C18 C22 -178.1(3) . . . . ? C14 C13 C18 C17 0.0 . . . . ? N12 C13 C18 C17 178.0(2) . . . . ? C14 C13 C18 C22 178.0(3) . . . . ? N12 C13 C18 C22 -4.0(3) . . . . ? C13 C14 C19 C20 115.3(3) . . . . ? C15 C14 C19 C20 -64.1(4) . . . . ? C13 C14 C19 C21 -121.4(3) . . . . ? C15 C14 C19 C21 59.2(4) . . . . ? C17 C18 C22 C24 -54.2(4) . . . . ? C13 C18 C22 C24 127.8(3) . . . . ? C17 C18 C22 C23 69.5(3) . . . . ? C13 C18 C22 C23 -108.5(3) . . . . ? C31 C31 N32 C33 177.6(4) 3_767 . . . ? C31 N32 C33 C34 -90.0(3) . . . . ? C31 N32 C33 C38 92.9(3) . . . . ? C38 C33 C34 C35 0.0 . . . . ? N32 C33 C34 C35 -177.1(2) . . . . ? C38 C33 C34 C39 -175.3(3) . . . . ? N32 C33 C34 C39 7.6(3) . . . . ? C33 C34 C35 C36 0.0 . . . . ? C39 C34 C35 C36 175.6(3) . . . . ? C34 C35 C36 C37 0.0 . . . . ? C35 C36 C37 C38 0.0 . . . . ? C36 C37 C38 C33 0.0 . . . . ? C36 C37 C38 C42 -177.5(3) . . . . ? C34 C33 C38 C37 0.0 . . . . ? N32 C33 C38 C37 177.1(2) . . . . ? C34 C33 C38 C42 177.3(3) . . . . ? N32 C33 C38 C42 -5.6(3) . . . . ? C35 C34 C39 C41 57.3(4) . . . . ? C33 C34 C39 C41 -127.2(4) . . . . ? C35 C34 C39 C40 -66.4(4) . . . . ? C33 C34 C39 C40 109.0(4) . . . . ? C37 C38 C42 C43 64.9(4) . . . . ? C33 C38 C42 C43 -112.5(4) . . . . ? C37 C38 C42 C44 -58.5(4) . . . . ? C33 C38 C42 C44 124.1(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N12 H12A Cl1 0.92 2.25 3.067(3) 147.9 . N12 H12B Cl2 0.92 2.25 3.084(3) 150.4 . N32 H32B Cl1 0.92 2.21 3.092(3) 160.2 . N32 H32A Cl2 0.92 2.30 3.168(3) 156.9 . _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.655 _refine_diff_density_min -0.466 _refine_diff_density_rms 0.072 data_5 _database_code_depnum_ccdc_archive 'CCDC 676354' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H38 Cl4 N2 P2' _chemical_formula_sum 'C26 H38 Cl4 N2 P2' _chemical_formula_weight 582.32 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' Cl Cl 0.1484 0.1585 '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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.4412(5) _cell_length_b 9.6026(2) _cell_length_c 19.6484(5) _cell_angle_alpha 90.00 _cell_angle_beta 105.678(2) _cell_angle_gamma 90.00 _cell_volume 2986.64(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 14144 _cell_measurement_theta_min 2.04 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 0.522 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7449 _exptl_absorpt_correction_T_max 0.8699 _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa-CCD' _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28460 _diffrn_reflns_av_R_equivalents 0.0630 _diffrn_reflns_av_sigmaI/netI 0.0528 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 25.03 _reflns_number_total 5278 _reflns_number_gt 3903 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Nonius, 1997-2001)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 2001)' _computing_publication_material SHELXTL/PC _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^)+(0.0466P)^2^+0.4694P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5278 _refine_ls_number_parameters 283 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.0988 _refine_ls_wR_factor_gt 0.0908 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 0.28099(4) 0.57162(7) 0.43458(3) 0.02539(17) Uani 1 1 d . . . Cl11 Cl 0.25135(4) 0.35878(7) 0.42849(4) 0.03917(19) Uani 1 1 d . . . Cl12 Cl 0.15669(4) 0.64166(7) 0.40775(4) 0.03721(18) Uani 1 1 d . . . P2 P 0.23204(4) 0.68385(7) 0.10380(3) 0.02494(17) Uani 1 1 d . . . Cl21 Cl 0.25926(4) 0.89732(6) 0.11662(3) 0.03456(18) Uani 1 1 d . . . Cl22 Cl 0.35561(4) 0.61670(7) 0.14614(3) 0.03519(18) Uani 1 1 d . . . N1 N 0.30724(11) 0.60136(18) 0.36103(9) 0.0187(4) Uani 1 1 d . . . C2 C 0.25951(14) 0.5590(2) 0.28917(11) 0.0214(5) Uani 1 1 d . . . H2A H 0.2114 0.4994 0.2919 0.026 Uiso 1 1 calc R . . H2B H 0.2966 0.5040 0.2672 0.026 Uiso 1 1 calc R . . C3 C 0.22674(14) 0.6864(2) 0.24371(11) 0.0205(5) Uani 1 1 d . . . H3A H 0.1830 0.7331 0.2617 0.025 Uiso 1 1 calc R . . H3B H 0.2737 0.7530 0.2474 0.025 Uiso 1 1 calc R . . N4 N 0.19051(11) 0.64863(19) 0.16901(9) 0.0199(4) Uani 1 1 d . . . C11 C 0.39034(7) 0.65825(14) 0.37018(8) 0.0192(5) Uani 1 1 d G . . C12 C 0.40359(8) 0.80069(13) 0.37986(8) 0.0213(5) Uani 1 1 d G . . C13 C 0.48411(9) 0.85560(11) 0.38931(8) 0.0298(6) Uani 1 1 d G . . H13A H 0.4932 0.9530 0.3959 0.036 Uiso 1 1 calc R . . C14 C 0.55137(7) 0.76808(16) 0.38908(9) 0.0336(6) Uani 1 1 d G . . H14A H 0.6064 0.8056 0.3955 0.040 Uiso 1 1 calc R . . C15 C 0.53812(7) 0.62564(15) 0.37940(9) 0.0307(6) Uani 1 1 d G . . H15A H 0.5841 0.5658 0.3792 0.037 Uiso 1 1 calc R . . C16 C 0.45760(9) 0.57073(11) 0.36995(8) 0.0223(5) Uani 1 1 d G . . C17 C 0.33237(16) 0.9021(2) 0.38212(12) 0.0262(6) Uani 1 1 d . . . H17A H 0.2780 0.8492 0.3680 0.031 Uiso 1 1 calc R . . C18 C 0.32508(18) 1.0243(3) 0.33081(13) 0.0428(8) Uani 1 1 d . . . H18A H 0.3185 0.9886 0.2829 0.064 Uiso 1 1 calc R . . H18B H 0.3763 1.0814 0.3450 0.064 Uiso 1 1 calc R . . H18C H 0.2759 1.0811 0.3317 0.064 Uiso 1 1 calc R . . C19 C 0.34313(18) 0.9564(3) 0.45723(13) 0.0418(7) Uani 1 1 d . . . H19A H 0.3481 0.8776 0.4898 0.063 Uiso 1 1 calc R . . H19B H 0.2939 1.0129 0.4586 0.063 Uiso 1 1 calc R . . H19C H 0.3943 1.0136 0.4715 0.063 Uiso 1 1 calc R . . C20 C 0.44665(15) 0.4120(2) 0.36114(12) 0.0245(6) Uani 1 1 d . . . H20A H 0.3857 0.3898 0.3550 0.029 Uiso 1 1 calc R . . C21 C 0.47060(17) 0.3603(3) 0.29544(13) 0.0366(7) Uani 1 1 d . . . H21A H 0.4622 0.2593 0.2910 0.055 Uiso 1 1 calc R . . H21B H 0.5300 0.3822 0.2998 0.055 Uiso 1 1 calc R . . H21C H 0.4349 0.4063 0.2534 0.055 Uiso 1 1 calc R . . C22 C 0.49828(16) 0.3360(3) 0.42741(12) 0.0323(6) Uani 1 1 d . . . H22A H 0.4900 0.2353 0.4209 0.048 Uiso 1 1 calc R . . H22B H 0.4795 0.3659 0.4684 0.048 Uiso 1 1 calc R . . H22C H 0.5583 0.3582 0.4353 0.048 Uiso 1 1 calc R . . C31 C 0.10699(7) 0.58942(14) 0.14754(8) 0.0215(5) Uani 1 1 d G . . C32 C 0.09610(8) 0.44815(13) 0.13239(8) 0.0250(6) Uani 1 1 d G . . C33 C 0.01520(10) 0.39298(11) 0.10866(9) 0.0342(7) Uani 1 1 d G . . H33A H 0.0078 0.2964 0.0983 0.041 Uiso 1 1 calc R . . C34 C -0.05481(7) 0.47907(16) 0.10008(9) 0.0395(7) Uani 1 1 d G . . H34A H -0.1101 0.4414 0.0839 0.047 Uiso 1 1 calc R . . C35 C -0.04392(8) 0.62034(15) 0.11523(9) 0.0357(7) Uani 1 1 d G . . H35A H -0.0918 0.6792 0.1094 0.043 Uiso 1 1 calc R . . C36 C 0.03698(9) 0.67552(11) 0.13896(8) 0.0251(6) Uani 1 1 d G . . C37 C 0.17125(15) 0.3479(2) 0.14155(12) 0.0262(6) Uani 1 1 d . . . H37A H 0.2239 0.4021 0.1628 0.031 Uiso 1 1 calc R . . C38 C 0.17748(18) 0.2921(3) 0.07056(13) 0.0431(7) Uani 1 1 d . . . H38A H 0.1801 0.3701 0.0391 0.065 Uiso 1 1 calc R . . H38B H 0.1277 0.2349 0.0493 0.065 Uiso 1 1 calc R . . H38C H 0.2286 0.2352 0.0776 0.065 Uiso 1 1 calc R . . C39 C 0.16776(18) 0.2277(3) 0.19210(14) 0.0388(7) Uani 1 1 d . . . H39A H 0.1645 0.2654 0.2376 0.058 Uiso 1 1 calc R . . H39B H 0.2188 0.1705 0.1992 0.058 Uiso 1 1 calc R . . H39C H 0.1178 0.1703 0.1718 0.058 Uiso 1 1 calc R . . C40 C 0.04581(15) 0.8335(2) 0.15094(12) 0.0259(6) Uani 1 1 d . . . H40A H 0.1072 0.8546 0.1711 0.031 Uiso 1 1 calc R . . C41 C -0.00077(18) 0.8849(3) 0.20350(14) 0.0406(7) Uani 1 1 d . . . H41A H 0.0071 0.9857 0.2099 0.061 Uiso 1 1 calc R . . H41B H 0.0218 0.8380 0.2490 0.061 Uiso 1 1 calc R . . H41C H -0.0611 0.8641 0.1854 0.061 Uiso 1 1 calc R . . C42 C 0.01600(16) 0.9096(2) 0.07980(12) 0.0324(6) Uani 1 1 d . . . H42A H 0.0219 1.0103 0.0876 0.049 Uiso 1 1 calc R . . H42B H -0.0434 0.8870 0.0577 0.049 Uiso 1 1 calc R . . H42C H 0.0504 0.8801 0.0487 0.049 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 0.0223(4) 0.0330(4) 0.0215(3) -0.0007(3) 0.0071(3) -0.0039(3) Cl11 0.0407(4) 0.0312(4) 0.0491(4) 0.0132(3) 0.0182(3) -0.0015(3) Cl12 0.0244(4) 0.0385(4) 0.0525(4) -0.0045(3) 0.0169(3) 0.0014(3) P2 0.0274(4) 0.0265(4) 0.0214(3) 0.0004(3) 0.0073(3) -0.0021(3) Cl21 0.0403(4) 0.0262(3) 0.0408(4) 0.0041(3) 0.0170(3) -0.0049(3) Cl22 0.0260(4) 0.0405(4) 0.0425(4) 0.0046(3) 0.0151(3) 0.0038(3) N1 0.0156(10) 0.0222(11) 0.0167(10) -0.0006(8) 0.0014(8) -0.0017(8) C2 0.0197(13) 0.0247(13) 0.0174(12) -0.0022(10) 0.0010(9) -0.0016(10) C3 0.0232(13) 0.0205(13) 0.0168(12) -0.0022(9) 0.0033(10) 0.0002(10) N4 0.0192(11) 0.0229(11) 0.0160(10) -0.0009(8) 0.0019(8) -0.0042(8) C11 0.0191(13) 0.0237(13) 0.0145(12) 0.0005(9) 0.0041(10) -0.0024(10) C12 0.0256(14) 0.0212(13) 0.0152(12) 0.0007(9) 0.0021(10) -0.0028(11) C13 0.0341(16) 0.0250(14) 0.0288(14) 0.0021(11) 0.0059(11) -0.0072(12) C14 0.0245(15) 0.0422(17) 0.0348(15) 0.0009(12) 0.0088(12) -0.0116(13) C15 0.0218(14) 0.0399(16) 0.0323(15) 0.0009(12) 0.0104(11) 0.0013(12) C16 0.0203(13) 0.0290(14) 0.0170(12) 0.0008(10) 0.0039(10) -0.0011(11) C17 0.0293(14) 0.0188(13) 0.0272(14) -0.0023(10) 0.0022(11) -0.0011(11) C18 0.059(2) 0.0252(15) 0.0364(16) 0.0055(12) -0.0010(14) 0.0062(14) C19 0.0532(19) 0.0381(17) 0.0332(16) -0.0072(13) 0.0102(14) 0.0084(14) C20 0.0238(14) 0.0232(13) 0.0251(13) -0.0001(10) 0.0042(10) 0.0040(11) C21 0.0457(18) 0.0348(16) 0.0277(15) -0.0027(12) 0.0074(12) 0.0124(13) C22 0.0351(16) 0.0322(15) 0.0267(14) 0.0029(11) 0.0034(12) 0.0046(12) C31 0.0214(13) 0.0231(13) 0.0176(12) 0.0037(10) 0.0012(10) -0.0022(11) C32 0.0268(14) 0.0239(14) 0.0212(13) 0.0022(10) 0.0011(10) -0.0019(11) C33 0.0331(16) 0.0246(15) 0.0397(16) 0.0044(12) 0.0007(12) -0.0078(12) C34 0.0228(15) 0.0356(16) 0.0526(18) 0.0064(13) -0.0026(13) -0.0118(13) C35 0.0205(15) 0.0362(16) 0.0455(17) 0.0077(13) 0.0007(12) 0.0026(12) C36 0.0250(14) 0.0262(14) 0.0222(13) 0.0048(10) 0.0034(10) -0.0028(11) C37 0.0308(15) 0.0200(13) 0.0255(13) -0.0040(10) 0.0037(11) -0.0006(11) C38 0.0530(19) 0.0411(18) 0.0341(16) -0.0078(13) 0.0100(14) 0.0019(15) C39 0.0500(19) 0.0254(15) 0.0379(16) 0.0025(12) 0.0064(13) 0.0065(13) C40 0.0234(14) 0.0233(14) 0.0285(14) 0.0013(10) 0.0028(11) 0.0030(11) C41 0.0451(18) 0.0433(18) 0.0358(16) -0.0013(13) 0.0149(13) 0.0043(14) C42 0.0362(16) 0.0275(15) 0.0314(15) 0.0043(11) 0.0058(12) 0.0041(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 N1 1.6411(19) . ? P1 Cl12 2.0795(9) . ? P1 Cl11 2.0970(9) . ? P2 N4 1.6417(19) . ? P2 Cl22 2.0788(9) . ? P2 Cl21 2.0988(9) . ? N1 C11 1.437(2) . ? N1 C2 1.475(3) . ? C2 C3 1.525(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N4 1.473(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? N4 C31 1.440(2) . ? C11 C12 1.3900 . ? C11 C16 1.3900 . ? C12 C13 1.3900 . ? C12 C17 1.533(3) . ? C13 C14 1.3900 . ? C13 H13A 0.9500 . ? C14 C15 1.3900 . ? C14 H14A 0.9500 . ? C15 C16 1.3900 . ? C15 H15A 0.9500 . ? C16 C20 1.539(2) . ? C17 C19 1.530(3) . ? C17 C18 1.531(3) . ? C17 H17A 1.0000 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.531(3) . ? C20 C22 1.533(3) . ? C20 H20A 1.0000 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C31 C32 1.3900 . ? C31 C36 1.3900 . ? C32 C33 1.3900 . ? C32 C37 1.538(3) . ? C33 C34 1.3900 . ? C33 H33A 0.9500 . ? C34 C35 1.3900 . ? C34 H34A 0.9500 . ? C35 C36 1.3900 . ? C35 H35A 0.9500 . ? C36 C40 1.537(2) . ? C37 C38 1.524(3) . ? C37 C39 1.534(3) . ? C37 H37A 1.0000 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 C41 1.524(3) . ? C40 C42 1.536(3) . ? C40 H40A 1.0000 . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? 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 Cl12 101.23(7) . . ? N1 P1 Cl11 103.40(7) . . ? Cl12 P1 Cl11 95.94(4) . . ? N4 P2 Cl22 101.03(7) . . ? N4 P2 Cl21 103.16(7) . . ? Cl22 P2 Cl21 95.81(4) . . ? C11 N1 C2 117.80(17) . . ? C11 N1 P1 115.05(12) . . ? C2 N1 P1 126.62(15) . . ? N1 C2 C3 110.61(18) . . ? N1 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? N4 C3 C2 111.71(17) . . ? N4 C3 H3A 109.3 . . ? C2 C3 H3A 109.3 . . ? N4 C3 H3B 109.3 . . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 107.9 . . ? C31 N4 C3 119.09(17) . . ? C31 N4 P2 114.67(12) . . ? C3 N4 P2 125.85(15) . . ? C12 C11 C16 120.0 . . ? C12 C11 N1 119.99(11) . . ? C16 C11 N1 120.01(11) . . ? C11 C12 C13 120.0 . . ? C11 C12 C17 122.43(13) . . ? C13 C12 C17 117.55(13) . . ? C14 C13 C12 120.0 . . ? C14 C13 H13A 120.0 . . ? C12 C13 H13A 120.0 . . ? C13 C14 C15 120.0 . . ? C13 C14 H14A 120.0 . . ? C15 C14 H14A 120.0 . . ? C16 C15 C14 120.0 . . ? C16 C15 H15A 120.0 . . ? C14 C15 H15A 120.0 . . ? C15 C16 C11 120.0 . . ? C15 C16 C20 117.97(12) . . ? C11 C16 C20 122.02(13) . . ? C19 C17 C18 110.0(2) . . ? C19 C17 C12 110.76(18) . . ? C18 C17 C12 113.1(2) . . ? C19 C17 H17A 107.6 . . ? C18 C17 H17A 107.6 . . ? C12 C17 H17A 107.6 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C22 110.63(19) . . ? C21 C20 C16 111.53(18) . . ? C22 C20 C16 110.78(17) . . ? C21 C20 H20A 107.9 . . ? C22 C20 H20A 107.9 . . ? C16 C20 H20A 107.9 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C32 C31 C36 120.0 . . ? C32 C31 N4 120.36(12) . . ? C36 C31 N4 119.57(12) . . ? C31 C32 C33 120.0 . . ? C31 C32 C37 122.19(12) . . ? C33 C32 C37 117.80(12) . . ? C34 C33 C32 120.0 . . ? C34 C33 H33A 120.0 . . ? C32 C33 H33A 120.0 . . ? C33 C34 C35 120.0 . . ? C33 C34 H34A 120.0 . . ? C35 C34 H34A 120.0 . . ? C36 C35 C34 120.0 . . ? C36 C35 H35A 120.0 . . ? C34 C35 H35A 120.0 . . ? C35 C36 C31 120.0 . . ? C35 C36 C40 118.04(13) . . ? C31 C36 C40 121.87(13) . . ? C38 C37 C39 110.6(2) . . ? C38 C37 C32 111.34(18) . . ? C39 C37 C32 112.2(2) . . ? C38 C37 H37A 107.5 . . ? C39 C37 H37A 107.5 . . ? C32 C37 H37A 107.5 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C37 C39 H39A 109.5 . . ? C37 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C37 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C41 C40 C42 111.6(2) . . ? C41 C40 C36 112.31(19) . . ? C42 C40 C36 109.67(18) . . ? C41 C40 H40A 107.7 . . ? C42 C40 H40A 107.7 . . ? C36 C40 H40A 107.7 . . ? C40 C41 H41A 109.5 . . ? C40 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C40 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C40 C42 H42A 109.5 . . ? C40 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C40 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl12 P1 N1 C11 138.19(12) . . . . ? Cl11 P1 N1 C11 -122.85(12) . . . . ? Cl12 P1 N1 C2 -50.40(18) . . . . ? Cl11 P1 N1 C2 48.56(18) . . . . ? C11 N1 C2 C3 -74.4(2) . . . . ? P1 N1 C2 C3 114.4(2) . . . . ? N1 C2 C3 N4 171.08(18) . . . . ? C2 C3 N4 C31 78.1(2) . . . . ? C2 C3 N4 P2 -109.4(2) . . . . ? Cl22 P2 N4 C31 -138.33(12) . . . . ? Cl21 P2 N4 C31 122.95(12) . . . . ? Cl22 P2 N4 C3 48.91(18) . . . . ? Cl21 P2 N4 C3 -49.80(18) . . . . ? C2 N1 C11 C12 104.53(17) . . . . ? P1 N1 C11 C12 -83.26(14) . . . . ? C2 N1 C11 C16 -76.02(19) . . . . ? P1 N1 C11 C16 96.19(14) . . . . ? C16 C11 C12 C13 0.0 . . . . ? N1 C11 C12 C13 179.45(14) . . . . ? C16 C11 C12 C17 -178.74(16) . . . . ? N1 C11 C12 C17 0.71(18) . . . . ? C11 C12 C13 C14 0.0 . . . . ? C17 C12 C13 C14 178.80(15) . . . . ? C12 C13 C14 C15 0.0 . . . . ? C13 C14 C15 C16 0.0 . . . . ? C14 C15 C16 C11 0.0 . . . . ? C14 C15 C16 C20 -178.63(15) . . . . ? C12 C11 C16 C15 0.0 . . . . ? N1 C11 C16 C15 -179.45(14) . . . . ? C12 C11 C16 C20 178.57(16) . . . . ? N1 C11 C16 C20 -0.87(17) . . . . ? C11 C12 C17 C19 108.51(19) . . . . ? C13 C12 C17 C19 -70.3(2) . . . . ? C11 C12 C17 C18 -127.49(17) . . . . ? C13 C12 C17 C18 53.7(2) . . . . ? C15 C16 C20 C21 -61.7(2) . . . . ? C11 C16 C20 C21 119.68(17) . . . . ? C15 C16 C20 C22 62.0(2) . . . . ? C11 C16 C20 C22 -116.63(18) . . . . ? C3 N4 C31 C32 -105.56(18) . . . . ? P2 N4 C31 C32 81.16(15) . . . . ? C3 N4 C31 C36 77.31(19) . . . . ? P2 N4 C31 C36 -95.97(14) . . . . ? C36 C31 C32 C33 0.0 . . . . ? N4 C31 C32 C33 -177.13(15) . . . . ? C36 C31 C32 C37 -179.44(16) . . . . ? N4 C31 C32 C37 3.43(18) . . . . ? C31 C32 C33 C34 0.0 . . . . ? C37 C32 C33 C34 179.47(16) . . . . ? C32 C33 C34 C35 0.0 . . . . ? C33 C34 C35 C36 0.0 . . . . ? C34 C35 C36 C31 0.0 . . . . ? C34 C35 C36 C40 176.59(16) . . . . ? C32 C31 C36 C35 0.0 . . . . ? N4 C31 C36 C35 177.15(15) . . . . ? C32 C31 C36 C40 -176.45(16) . . . . ? N4 C31 C36 C40 0.70(18) . . . . ? C31 C32 C37 C38 -113.10(19) . . . . ? C33 C32 C37 C38 67.4(2) . . . . ? C31 C32 C37 C39 122.41(18) . . . . ? C33 C32 C37 C39 -57.0(2) . . . . ? C35 C36 C40 C41 57.5(2) . . . . ? C31 C36 C40 C41 -125.93(18) . . . . ? C35 C36 C40 C42 -67.1(2) . . . . ? C31 C36 C40 C42 109.41(18) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.445 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.056