# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Maria Rosario Diaz' _publ_contact_author_email mrdf@uniovi.es loop_ _publ_author_name _publ_author_address 'Javier Ruiz' ; Departamento de Qu\'imica Org\'anica e Inorg\'anica. Universidad de Oviedo 33006-Oviedo Spain ; "Marta P\'erez Gonzalo" ; Departamento de Qu\'imica Org\'anica e Inorg\'anica. Universidad de Oviedo 33006-Oviedo Spain ; "Maril\'in Vivanco" ; Departamento de Qu\'imica Org\'anica e Inorg\'anica. Universidad de Oviedo 33006-Oviedo Spain ; "Mar\'ia Rosario D\'iaz" ; Departamento de Qu\'imica F\'isica y Anal\'itica Universidad de Oviedo 33006-Oviedo Spain ; "Santiago Garc\'ia-Granda" ; Departamento de Qu\'imica F\'isica y Anal\'itica Universidad de Oviedo 33006-Oviedo Spain ; _publ_section_title ; Three-component reaction involving isocyanide, phosphine and ketenimine functionalities ; #========================================================================== data_3a _database_code_depnum_ccdc_archive 'CCDC 801483' #TrackingRef '- 3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C37 H36 N2 O P2, C H2 Cl2' _chemical_formula_sum 'C38 H38 Cl2 N2 O P2' _chemical_formula_weight 671.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 11.6478(6) _cell_length_b 18.9850(14) _cell_length_c 16.1788(11) _cell_angle_alpha 90.00 _cell_angle_beta 99.847(4) _cell_angle_gamma 90.00 _cell_volume 3525.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6504 _cell_measurement_theta_min 3 _cell_measurement_theta_max 70 _exptl_crystal_description Prismatic _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_correction_type refdelf _exptl_absorpt_coefficient_mu 2.761 _exptl_absorpt_process_details ; Parkin S,Moezzi B & Hope H, (1995) J. Appl. Cryst. 28, 53-56 Cubic fit to sin(theta)/lambda - 24 parameters ; _exptl_absorpt_correction_T_min 0.765 _exptl_absorpt_correction_T_max 0.804 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.0500854 _diffrn_orient_matrix_ub_12 -0.0398698 _diffrn_orient_matrix_ub_13 -0.0253853 _diffrn_orient_matrix_ub_21 0.0085169 _diffrn_orient_matrix_ub_22 0.0165258 _diffrn_orient_matrix_ub_23 -0.057328 _diffrn_orient_matrix_ub_31 0.0707938 _diffrn_orient_matrix_ub_32 -0.0301954 _diffrn_orient_matrix_ub_33 0.0021431 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6543 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 69.63 _reflns_number_total 6543 _reflns_number_gt 5204 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 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^)+(0.0776P)^2^+0.5906P] 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 6543 _refine_ls_number_parameters 546 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0606 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1388 _refine_ls_wR_factor_gt 0.1293 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.66311(4) 0.13474(3) 0.17981(3) 0.04708(16) Uani 1 1 d . . . P2 P 0.69395(4) 0.25705(3) 0.29878(3) 0.04527(16) Uani 1 1 d . . . O1 O 0.63608(13) 0.19372(8) 0.11912(8) 0.0572(4) Uani 1 1 d . . . N1 N 0.71248(14) 0.25406(9) 0.40273(10) 0.0489(4) Uani 1 1 d . . . N2 N 0.70831(16) 0.06326(9) 0.36788(10) 0.0562(4) Uani 1 1 d . . . C1 C 0.68770(17) 0.16744(11) 0.28240(12) 0.0488(5) Uani 1 1 d . . . C2 C 0.70580(16) 0.13114(11) 0.36038(12) 0.0478(4) Uani 1 1 d . . . C3 C 0.7274(2) 0.18172(12) 0.43373(14) 0.0562(5) Uani 1 1 d . . . C4 C 0.75535(19) 0.31213(12) 0.46397(13) 0.0559(5) Uani 1 1 d . . . C5 C 0.7101(3) 0.29770(17) 0.54575(16) 0.0766(8) Uani 1 1 d . . . C6 C 0.7074(3) 0.38241(13) 0.43000(16) 0.0740(7) Uani 1 1 d . . . H6A H 0.6238 0.3807 0.4199 0.111 Uiso 1 1 calc R . . H6B H 0.7345 0.3923 0.3784 0.111 Uiso 1 1 calc R . . H6C H 0.7335 0.4187 0.4701 0.111 Uiso 1 1 calc R . . C7 C 0.8877(3) 0.3135(2) 0.4805(3) 0.0851(9) Uani 1 1 d . . . C11 C 0.54593(17) 0.07101(11) 0.17026(12) 0.0501(5) Uani 1 1 d . . . C12 C 0.5421(2) 0.01315(13) 0.11752(15) 0.0631(6) Uani 1 1 d . . . C13 C 0.4447(2) -0.02985(15) 0.10312(19) 0.0755(7) Uani 1 1 d . . . C14 C 0.3510(2) -0.01566(17) 0.14035(18) 0.0770(7) Uani 1 1 d . . . C15 C 0.3538(2) 0.04088(19) 0.19312(17) 0.0810(8) Uani 1 1 d . . . C16 C 0.4505(2) 0.08427(16) 0.20853(15) 0.0679(6) Uani 1 1 d . . . C21 C 0.79153(17) 0.08827(11) 0.15884(13) 0.0525(5) Uani 1 1 d . . . C22 C 0.8602(2) 0.04564(15) 0.21695(17) 0.0694(6) Uani 1 1 d . . . C23 C 0.9628(3) 0.01776(18) 0.1994(2) 0.0880(9) Uani 1 1 d . . . C24 C 0.9974(3) 0.03146(19) 0.1246(3) 0.0944(10) Uani 1 1 d . . . C25 C 0.9291(3) 0.07305(18) 0.0658(2) 0.0914(9) Uani 1 1 d . . . C26 C 0.8263(2) 0.10093(15) 0.08233(18) 0.0709(7) Uani 1 1 d . . . C31 C 0.81178(17) 0.29876(11) 0.25717(12) 0.0506(5) Uani 1 1 d . . . C32 C 0.90803(19) 0.25713(14) 0.25021(15) 0.0609(6) Uani 1 1 d . . . C33 C 1.0023(2) 0.28598(18) 0.22017(18) 0.0763(7) Uani 1 1 d . . . C34 C 1.0004(2) 0.35565(17) 0.19667(19) 0.0793(8) Uani 1 1 d . . . C35 C 0.9063(2) 0.39758(15) 0.20326(16) 0.0691(6) Uani 1 1 d . . . C36 C 0.8124(2) 0.36943(13) 0.23363(14) 0.0577(5) Uani 1 1 d . . . C41 C 0.56159(17) 0.30369(11) 0.25708(13) 0.0508(5) Uani 1 1 d . . . C42 C 0.4715(2) 0.30308(14) 0.30323(18) 0.0694(6) Uani 1 1 d . . . C43 C 0.3647(2) 0.33318(17) 0.2704(2) 0.0873(9) Uani 1 1 d . . . C44 C 0.3483(2) 0.36465(15) 0.1937(2) 0.0842(9) Uani 1 1 d . . . C45 C 0.4353(2) 0.36441(14) 0.14685(19) 0.0739(7) Uani 1 1 d . . . C46 C 0.5419(2) 0.33341(12) 0.17763(14) 0.0596(5) Uani 1 1 d . . . C51 C 0.73106(19) 0.03098(11) 0.44764(13) 0.0547(5) Uani 1 1 d . . . C52 C 0.6507(2) 0.02986(13) 0.50200(15) 0.0660(6) Uani 1 1 d . . . C53 C 0.6734(3) -0.00687(15) 0.57643(16) 0.0770(7) Uani 1 1 d . . . C54 C 0.7764(3) -0.04276(15) 0.59943(17) 0.0795(8) Uani 1 1 d . . . C55 C 0.8560(3) -0.04211(16) 0.54641(18) 0.0805(8) Uani 1 1 d . . . C56 C 0.8339(2) -0.00614(14) 0.47102(17) 0.0686(6) Uani 1 1 d . . . Cl1 Cl 0.16953(10) 0.23736(7) 0.42001(7) 0.1319(4) Uani 1 1 d . . . Cl2 Cl 0.40800(9) 0.20776(8) 0.48680(7) 0.1431(5) Uani 1 1 d . . . C8 C 0.2663(3) 0.2077(2) 0.5066(2) 0.0900(9) Uani 1 1 d . . . H3A H 0.804(2) 0.1742(13) 0.4632(15) 0.067(7) Uiso 1 1 d . . . H3B H 0.678(2) 0.1739(15) 0.4733(19) 0.088(9) Uiso 1 1 d . . . H5A H 0.621(3) 0.2981(15) 0.5344(17) 0.080(8) Uiso 1 1 d . . . H5B H 0.732(2) 0.3383(17) 0.5830(19) 0.089(8) Uiso 1 1 d . . . H5C H 0.732(3) 0.254(2) 0.570(2) 0.110(12) Uiso 1 1 d . . . H7A H 0.920(3) 0.2678(19) 0.499(2) 0.095(10) Uiso 1 1 d . . . H7B H 0.917(3) 0.322(2) 0.433(3) 0.121(14) Uiso 1 1 d . . . H7C H 0.908(3) 0.348(2) 0.520(2) 0.109(11) Uiso 1 1 d . . . H8A H 0.266(3) 0.236(2) 0.551(3) 0.128(14) Uiso 1 1 d . . . H8B H 0.250(3) 0.1572(18) 0.5188(19) 0.095(9) Uiso 1 1 d . . . H12 H 0.613(2) 0.0053(12) 0.0904(14) 0.061(6) Uiso 1 1 d . . . H13 H 0.447(3) -0.0665(17) 0.0667(19) 0.093(10) Uiso 1 1 d . . . H14 H 0.281(3) -0.0465(17) 0.1266(18) 0.096(9) Uiso 1 1 d . . . H15 H 0.284(3) 0.0599(17) 0.2180(19) 0.102(9) Uiso 1 1 d . . . H16 H 0.454(2) 0.1224(14) 0.2451(16) 0.069(7) Uiso 1 1 d . . . H22 H 0.837(2) 0.0371(15) 0.2702(18) 0.079(8) Uiso 1 1 d . . . H23 H 1.003(3) -0.0072(18) 0.245(2) 0.104(11) Uiso 1 1 d . . . H24 H 1.076(3) 0.0112(18) 0.109(2) 0.108(10) Uiso 1 1 d . . . H25 H 0.956(3) 0.0835(17) 0.013(2) 0.107(10) Uiso 1 1 d . . . H26 H 0.782(2) 0.1276(16) 0.0435(18) 0.082(9) Uiso 1 1 d . . . H32 H 0.906(2) 0.2075(14) 0.2622(16) 0.067(7) Uiso 1 1 d . . . H33 H 1.062(3) 0.2598(18) 0.216(2) 0.105(11) Uiso 1 1 d . . . H34 H 1.066(3) 0.373(2) 0.176(2) 0.127(12) Uiso 1 1 d . . . H35 H 0.907(2) 0.4464(16) 0.1893(16) 0.078(8) Uiso 1 1 d . . . H36 H 0.750(2) 0.3959(15) 0.2396(16) 0.077(8) Uiso 1 1 d . . . H42 H 0.480(2) 0.2797(14) 0.3587(18) 0.075(7) Uiso 1 1 d . . . H43 H 0.307(3) 0.3310(16) 0.3074(19) 0.094(9) Uiso 1 1 d . . . H44 H 0.272(3) 0.3858(17) 0.1718(19) 0.096(9) Uiso 1 1 d . . . H45 H 0.427(2) 0.3851(16) 0.0925(19) 0.087(8) Uiso 1 1 d . . . H46 H 0.605(2) 0.3343(14) 0.1428(16) 0.078(8) Uiso 1 1 d . . . H52 H 0.580(2) 0.0523(14) 0.4868(15) 0.068(7) Uiso 1 1 d . . . H53 H 0.616(3) -0.0074(18) 0.611(2) 0.108(11) Uiso 1 1 d . . . H54 H 0.798(2) -0.0715(16) 0.6547(19) 0.087(8) Uiso 1 1 d . . . H55 H 0.922(3) -0.0674(18) 0.559(2) 0.103(11) Uiso 1 1 d . . . H56 H 0.886(2) -0.0048(13) 0.4323(16) 0.071(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0500(3) 0.0486(3) 0.0420(3) 0.0002(2) 0.0061(2) 0.0025(2) P2 0.0451(3) 0.0458(3) 0.0434(3) 0.0023(2) 0.0035(2) 0.0029(2) O1 0.0658(9) 0.0578(9) 0.0477(8) 0.0062(6) 0.0086(6) 0.0040(7) N1 0.0539(9) 0.0458(9) 0.0448(9) 0.0000(7) 0.0023(7) -0.0007(7) N2 0.0698(11) 0.0482(10) 0.0488(9) 0.0033(8) 0.0049(8) -0.0027(8) C1 0.0538(11) 0.0459(11) 0.0456(10) 0.0016(8) 0.0053(8) 0.0015(9) C2 0.0483(10) 0.0476(12) 0.0459(10) 0.0019(8) 0.0042(8) 0.0013(8) C3 0.0707(14) 0.0490(12) 0.0458(11) 0.0045(9) 0.0008(10) 0.0025(10) C4 0.0650(13) 0.0525(12) 0.0485(11) -0.0067(9) 0.0050(9) -0.0041(10) C5 0.112(2) 0.0687(18) 0.0500(13) -0.0096(12) 0.0162(14) -0.0086(16) C6 0.1036(19) 0.0524(14) 0.0653(15) -0.0068(11) 0.0121(13) -0.0020(13) C7 0.0677(17) 0.090(2) 0.091(2) -0.0214(19) -0.0041(16) -0.0142(16) C11 0.0496(11) 0.0541(12) 0.0447(10) 0.0043(9) 0.0023(8) 0.0019(9) C12 0.0573(13) 0.0596(14) 0.0704(14) -0.0064(11) 0.0048(11) 0.0015(11) C13 0.0699(16) 0.0627(16) 0.0878(18) -0.0088(14) -0.0032(13) -0.0070(12) C14 0.0637(15) 0.0834(19) 0.0799(17) 0.0102(15) 0.0009(13) -0.0174(14) C15 0.0575(14) 0.117(2) 0.0707(16) 0.0030(16) 0.0177(12) -0.0100(15) C16 0.0611(14) 0.0853(18) 0.0585(13) -0.0085(13) 0.0136(11) -0.0024(12) C21 0.0516(11) 0.0493(12) 0.0568(12) -0.0063(9) 0.0100(9) -0.0032(9) C22 0.0661(14) 0.0723(16) 0.0685(15) -0.0024(12) 0.0074(12) 0.0147(12) C23 0.0707(17) 0.090(2) 0.099(2) -0.0163(18) 0.0004(16) 0.0227(15) C24 0.0610(16) 0.095(2) 0.132(3) -0.031(2) 0.0297(18) 0.0035(15) C25 0.089(2) 0.090(2) 0.108(2) -0.0094(18) 0.0544(19) -0.0024(17) C26 0.0754(16) 0.0710(17) 0.0713(16) -0.0010(13) 0.0263(13) 0.0060(13) C31 0.0486(11) 0.0543(12) 0.0474(10) 0.0021(9) 0.0038(8) 0.0011(9) C32 0.0524(12) 0.0608(15) 0.0683(14) 0.0025(11) 0.0069(10) 0.0018(10) C33 0.0506(13) 0.094(2) 0.0857(18) 0.0001(15) 0.0158(12) 0.0054(13) C34 0.0642(15) 0.091(2) 0.0856(18) 0.0073(15) 0.0194(13) -0.0156(15) C35 0.0748(16) 0.0666(16) 0.0651(14) 0.0076(12) 0.0100(12) -0.0146(13) C36 0.0591(13) 0.0566(14) 0.0567(12) 0.0025(10) 0.0076(10) -0.0006(11) C41 0.0498(10) 0.0456(11) 0.0546(11) 0.0009(9) 0.0023(9) 0.0023(8) C42 0.0539(13) 0.0733(16) 0.0820(17) 0.0122(13) 0.0144(11) 0.0041(11) C43 0.0492(13) 0.091(2) 0.124(2) 0.0108(19) 0.0205(15) 0.0090(13) C44 0.0515(14) 0.0726(18) 0.119(2) 0.0095(16) -0.0113(15) 0.0080(12) C45 0.0719(16) 0.0639(16) 0.0747(16) 0.0070(13) -0.0199(13) 0.0051(12) C46 0.0625(13) 0.0568(13) 0.0552(12) 0.0006(10) -0.0025(10) 0.0072(10) C51 0.0667(13) 0.0442(11) 0.0507(11) 0.0012(9) 0.0033(9) -0.0066(9) C52 0.0753(16) 0.0609(14) 0.0617(14) 0.0055(11) 0.0112(12) -0.0005(12) C53 0.101(2) 0.0716(17) 0.0607(14) 0.0045(13) 0.0209(14) -0.0115(15) C54 0.109(2) 0.0662(16) 0.0590(15) 0.0123(12) 0.0007(14) -0.0065(15) C55 0.0827(18) 0.0741(18) 0.0772(17) 0.0156(14) -0.0077(15) 0.0028(15) C56 0.0662(14) 0.0652(15) 0.0729(15) 0.0142(12) 0.0081(12) -0.0020(12) Cl1 0.1354(8) 0.1478(9) 0.1104(7) 0.0083(6) 0.0153(6) 0.0393(7) Cl2 0.1085(7) 0.2041(13) 0.1201(8) 0.0457(8) 0.0293(6) -0.0208(7) C8 0.120(3) 0.084(2) 0.0717(18) -0.0026(16) 0.0304(17) -0.0023(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 O1 1.4871(15) . ? P1 C1 1.749(2) . ? P1 C11 1.811(2) . ? P1 C21 1.818(2) . ? P2 N1 1.6595(17) . ? P2 C1 1.721(2) . ? P2 C41 1.806(2) . ? P2 C31 1.811(2) . ? N1 C3 1.462(3) . ? N1 C4 1.509(3) . ? N2 C2 1.294(3) . ? N2 C51 1.412(3) . ? C1 C2 1.421(3) . ? C2 C3 1.514(3) . ? C3 H3A 0.95(3) . ? C3 H3B 0.94(3) . ? C4 C6 1.513(3) . ? C4 C7 1.519(4) . ? C4 C5 1.531(3) . ? C5 H5A 1.02(3) . ? C5 H5B 0.99(3) . ? C5 H5C 0.93(4) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.97(4) . ? C7 H7B 0.91(4) . ? C7 H7C 0.92(4) . ? C11 C16 1.384(3) . ? C11 C12 1.387(3) . ? C12 C13 1.385(3) . ? C12 H12 1.01(2) . ? C13 C14 1.361(4) . ? C13 H13 0.91(3) . ? C14 C15 1.368(4) . ? C14 H14 0.99(3) . ? C15 C16 1.384(4) . ? C15 H15 1.03(3) . ? C16 H16 0.93(3) . ? C21 C22 1.386(3) . ? C21 C26 1.387(3) . ? C22 C23 1.380(4) . ? C22 H22 0.96(3) . ? C23 C24 1.365(5) . ? C23 H23 0.93(3) . ? C24 C25 1.379(5) . ? C24 H24 1.07(3) . ? C25 C26 1.377(4) . ? C25 H25 0.99(4) . ? C26 H26 0.90(3) . ? C31 C32 1.392(3) . ? C31 C36 1.395(3) . ? C32 C33 1.387(4) . ? C32 H32 0.96(3) . ? C33 C34 1.375(4) . ? C33 H33 0.87(3) . ? C34 C35 1.373(4) . ? C34 H34 0.94(4) . ? C35 C36 1.381(3) . ? C35 H35 0.95(3) . ? C36 H36 0.90(3) . ? C41 C46 1.387(3) . ? C41 C42 1.388(3) . ? C42 C43 1.389(4) . ? C42 H42 0.99(3) . ? C43 C44 1.360(5) . ? C43 H43 0.97(3) . ? C44 C45 1.366(4) . ? C44 H44 0.98(3) . ? C45 C46 1.387(3) . ? C45 H45 0.95(3) . ? C46 H46 1.00(3) . ? C51 C56 1.386(3) . ? C51 C52 1.390(3) . ? C52 C53 1.377(4) . ? C52 H52 0.92(3) . ? C53 C54 1.375(4) . ? C53 H53 0.93(3) . ? C54 C55 1.366(4) . ? C54 H54 1.04(3) . ? C55 C56 1.383(4) . ? C55 H55 0.90(3) . ? C56 H56 0.95(3) . ? Cl1 C8 1.735(4) . ? Cl2 C8 1.734(4) . ? C8 H8A 0.90(4) . ? C8 H8B 1.00(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 C1 109.94(9) . . ? O1 P1 C11 112.05(9) . . ? C1 P1 C11 108.47(9) . . ? O1 P1 C21 109.29(9) . . ? C1 P1 C21 110.06(9) . . ? C11 P1 C21 106.99(10) . . ? N1 P2 C1 96.72(9) . . ? N1 P2 C41 110.50(9) . . ? C1 P2 C41 114.60(9) . . ? N1 P2 C31 114.59(9) . . ? C1 P2 C31 112.93(10) . . ? C41 P2 C31 107.43(9) . . ? C3 N1 C4 117.02(16) . . ? C3 N1 P2 111.53(13) . . ? C4 N1 P2 127.70(14) . . ? C2 N2 C51 121.04(18) . . ? C2 C1 P2 110.28(14) . . ? C2 C1 P1 130.21(16) . . ? P2 C1 P1 119.51(11) . . ? N2 C2 C1 124.30(19) . . ? N2 C2 C3 124.06(18) . . ? C1 C2 C3 111.58(18) . . ? N1 C3 C2 109.44(17) . . ? N1 C3 H3A 111.2(16) . . ? C2 C3 H3A 108.4(15) . . ? N1 C3 H3B 109.4(18) . . ? C2 C3 H3B 113.3(18) . . ? H3A C3 H3B 105(2) . . ? N1 C4 C6 110.22(17) . . ? N1 C4 C7 109.9(2) . . ? C6 C4 C7 110.5(2) . . ? N1 C4 C5 108.21(19) . . ? C6 C4 C5 108.1(2) . . ? C7 C4 C5 109.9(3) . . ? C4 C5 H5A 109.4(16) . . ? C4 C5 H5B 107.1(17) . . ? H5A C5 H5B 105(2) . . ? C4 C5 H5C 114(2) . . ? H5A C5 H5C 106(3) . . ? H5B C5 H5C 115(3) . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 H7A 111.3(18) . . ? C4 C7 H7B 112(2) . . ? H7A C7 H7B 104(3) . . ? C4 C7 H7C 105(2) . . ? H7A C7 H7C 112(3) . . ? H7B C7 H7C 112(3) . . ? C16 C11 C12 118.4(2) . . ? C16 C11 P1 119.43(18) . . ? C12 C11 P1 121.74(16) . . ? C13 C12 C11 120.6(2) . . ? C13 C12 H12 123.1(13) . . ? C11 C12 H12 116.3(13) . . ? C14 C13 C12 120.3(3) . . ? C14 C13 H13 123.4(19) . . ? C12 C13 H13 116.2(19) . . ? C13 C14 C15 119.7(3) . . ? C13 C14 H14 118.1(17) . . ? C15 C14 H14 122.2(17) . . ? C14 C15 C16 120.7(3) . . ? C14 C15 H15 125.7(18) . . ? C16 C15 H15 113.0(18) . . ? C15 C16 C11 120.2(3) . . ? C15 C16 H16 121.3(15) . . ? C11 C16 H16 118.5(15) . . ? C22 C21 C26 118.9(2) . . ? C22 C21 P1 123.68(18) . . ? C26 C21 P1 117.21(18) . . ? C23 C22 C21 120.3(3) . . ? C23 C22 H22 120.3(16) . . ? C21 C22 H22 119.4(16) . . ? C24 C23 C22 120.4(3) . . ? C24 C23 H23 128(2) . . ? C22 C23 H23 112(2) . . ? C23 C24 C25 119.8(3) . . ? C23 C24 H24 122.7(18) . . ? C25 C24 H24 117.5(18) . . ? C26 C25 C24 120.4(3) . . ? C26 C25 H25 121(2) . . ? C24 C25 H25 118.9(19) . . ? C25 C26 C21 120.2(3) . . ? C25 C26 H26 119.9(18) . . ? C21 C26 H26 119.9(18) . . ? C32 C31 C36 118.8(2) . . ? C32 C31 P2 116.99(17) . . ? C36 C31 P2 124.18(16) . . ? C33 C32 C31 120.0(2) . . ? C33 C32 H32 120.1(15) . . ? C31 C32 H32 119.7(14) . . ? C34 C33 C32 120.0(3) . . ? C34 C33 H33 120(2) . . ? C32 C33 H33 120(2) . . ? C35 C34 C33 120.7(3) . . ? C35 C34 H34 122(2) . . ? C33 C34 H34 118(2) . . ? C34 C35 C36 119.6(3) . . ? C34 C35 H35 120.6(16) . . ? C36 C35 H35 119.8(16) . . ? C35 C36 C31 120.7(2) . . ? C35 C36 H36 121.6(17) . . ? C31 C36 H36 117.7(17) . . ? C46 C41 C42 118.8(2) . . ? C46 C41 P2 122.77(17) . . ? C42 C41 P2 118.07(17) . . ? C41 C42 C43 120.0(3) . . ? C41 C42 H42 121.4(15) . . ? C43 C42 H42 118.5(15) . . ? C44 C43 C42 120.5(3) . . ? C44 C43 H43 125.2(18) . . ? C42 C43 H43 114.3(18) . . ? C43 C44 C45 120.2(2) . . ? C43 C44 H44 119.2(18) . . ? C45 C44 H44 120.6(18) . . ? C44 C45 C46 120.4(3) . . ? C44 C45 H45 122.6(17) . . ? C46 C45 H45 117.0(17) . . ? C41 C46 C45 120.1(2) . . ? C41 C46 H46 120.4(15) . . ? C45 C46 H46 119.4(15) . . ? C56 C51 C52 117.6(2) . . ? C56 C51 N2 119.2(2) . . ? C52 C51 N2 122.9(2) . . ? C53 C52 C51 120.8(3) . . ? C53 C52 H52 119.8(16) . . ? C51 C52 H52 119.4(16) . . ? C54 C53 C52 121.0(3) . . ? C54 C53 H53 121(2) . . ? C52 C53 H53 118(2) . . ? C55 C54 C53 118.7(3) . . ? C55 C54 H54 117.2(15) . . ? C53 C54 H54 124.0(15) . . ? C54 C55 C56 121.0(3) . . ? C54 C55 H55 120(2) . . ? C56 C55 H55 119(2) . . ? C55 C56 C51 120.9(3) . . ? C55 C56 H56 123.7(16) . . ? C51 C56 H56 115.4(16) . . ? Cl2 C8 Cl1 110.99(18) . . ? Cl2 C8 H8A 106(3) . . ? Cl1 C8 H8A 111(3) . . ? Cl2 C8 H8B 105.0(17) . . ? Cl1 C8 H8B 110.5(18) . . ? H8A C8 H8B 113(3) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 69.63 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.308 _refine_diff_density_min -0.410 _refine_diff_density_rms 0.040