# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_2 _database_code_depnum_ccdc_archive 'CCDC 930071' #TrackingRef '18670_web_deposit_cif_file_0_CalebMartin_1363713550.2.cif' _audit_creation_method SHELXL-2012 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C96 H112 N8 O8 P8, 4(C6 H6)' _chemical_formula_sum 'C120 H136 N8 O8 P8' _chemical_formula_weight 2066.12 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' _space_group_crystal_system monoclinic _space_group_IT_number 13 _space_group_name_H-M_alt 'P 2/c' _space_group_name_Hall '-P 2yc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 12.600(4) _cell_length_b 16.320(5) _cell_length_c 26.808(9) _cell_angle_alpha 90 _cell_angle_beta 92.213(11) _cell_angle_gamma 90 _cell_volume 5508(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8794 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 26.23 _exptl_crystal_description Rod _exptl_crystal_colour Red-Brown _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.246 _exptl_crystal_F_000 2192 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.210 _exptl_crystal_size_mid 0.110 _exptl_crystal_size_min 0.100 _exptl_absorpt_coefficient_mu 0.187 _shelx_estimated_absorpt_T_min 0.962 _shelx_estimated_absorpt_T_max 0.982 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.587851 _exptl_absorpt_correction_T_max 0.745372 _exptl_absorpt_process_details TWINABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean '512 x 512' _diffrn_reflns_number 15639 _diffrn_reflns_av_unetI/netI 0.0988 _diffrn_reflns_av_R_equivalents 0.0820 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.923 _diffrn_reflns_theta_max 26.781 _diffrn_reflns_theta_full 25.000 _diffrn_measured_fraction_theta_max 0.928 _diffrn_measured_fraction_theta_full 0.965 _diffrn_reflns_Laue_measured_fraction_max 0.928 _diffrn_reflns_Laue_measured_fraction_full 0.965 _diffrn_reflns_point_group_measured_fraction_max 0.928 _diffrn_reflns_point_group_measured_fraction_full 0.965 _reflns_number_total 15639 _reflns_number_gt 10943 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. These statistics refer to single and composite reflections containing twin component 1 only. ; _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-2012 (Sheldrick, 2012)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refined as a 2-component twin. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.1054P)^2^] 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 15639 _refine_ls_number_parameters 651 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1043 _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.1766 _refine_ls_wR_factor_gt 0.1524 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.42257(9) 0.45490(6) 0.17722(4) 0.0143(2) Uani 1 1 d . . . . . P2 P 0.53947(8) 0.53899(6) 0.21302(4) 0.0123(2) Uani 1 1 d . . . . . P3 P 0.44923(8) 0.65880(6) 0.21436(4) 0.0128(2) Uani 1 1 d . . . . . P4 P 0.55575(9) 0.74103(6) 0.17381(4) 0.0151(2) Uani 1 1 d . . . . . O1 O 0.7240(2) 0.33335(17) 0.07745(12) 0.0251(7) Uani 1 1 d . . . . . O2 O 0.4033(2) 0.19820(16) 0.08353(11) 0.0218(7) Uani 1 1 d . . . . . O3 O 0.2268(2) 0.86239(17) 0.08405(12) 0.0269(8) Uani 1 1 d . . . . . O4 O 0.5521(2) 0.99457(17) 0.07760(12) 0.0266(8) Uani 1 1 d . . . . . N1 N 0.5956(3) 0.38489(19) 0.12554(12) 0.0139(8) Uani 1 1 d . . . . . N2 N 0.4282(3) 0.32060(18) 0.12195(12) 0.0119(7) Uani 1 1 d . . . . . N3 N 0.3686(3) 0.81023(19) 0.12671(13) 0.0151(8) Uani 1 1 d . . . . . N4 N 0.5356(3) 0.87372(19) 0.11740(12) 0.0151(8) Uani 1 1 d . . . . . C1 C 0.4916(3) 0.3862(2) 0.14102(15) 0.0140(9) Uani 1 1 d . . . . . C2 C 0.6409(3) 0.3224(2) 0.09693(16) 0.0168(9) Uani 1 1 d . . . . . C3 C 0.5838(3) 0.2403(2) 0.09591(15) 0.0161(9) Uani 1 1 d . . . . . C4 C 0.4650(3) 0.2505(2) 0.09868(14) 0.0157(9) Uani 1 1 d . . . . . C5 C 0.6647(3) 0.4559(2) 0.13414(15) 0.0129(9) Uani 1 1 d . . . . . C6 C 0.6549(3) 0.5225(2) 0.10207(15) 0.0144(9) Uani 1 1 d . . . . . C7 C 0.7200(3) 0.5897(2) 0.11195(16) 0.0171(9) Uani 1 1 d . . . . . H7 H 0.7125 0.6370 0.0915 0.021 Uiso 1 1 calc R U . . . C8 C 0.7955(3) 0.5895(2) 0.15090(16) 0.0179(10) Uani 1 1 d . . . . . C9 C 0.8050(3) 0.5199(2) 0.18011(16) 0.0172(9) Uani 1 1 d . . . . . H9 H 0.8578 0.5187 0.2063 0.021 Uiso 1 1 calc R U . . . C10 C 0.7404(3) 0.4519(2) 0.17271(15) 0.0143(9) Uani 1 1 d . . . . . C11 C 0.4770(3) 0.8091(2) 0.13899(15) 0.0139(9) Uani 1 1 d . . . . . C12 C 0.3168(4) 0.8723(2) 0.09896(16) 0.0186(10) Uani 1 1 d . . . . . C13 C 0.3753(3) 0.9526(2) 0.09285(16) 0.0160(9) Uani 1 1 d . . . . . C14 C 0.4934(4) 0.9426(2) 0.09433(16) 0.0189(10) Uani 1 1 d . . . . . C15 C 0.3157(3) 0.3227(2) 0.12958(16) 0.0150(9) Uani 1 1 d . . . . . C16 C 0.2753(3) 0.2820(2) 0.17039(15) 0.0162(9) Uani 1 1 d . . . . . C17 C 0.1666(4) 0.2851(2) 0.17634(17) 0.0219(10) Uani 1 1 d . . . . . H17 H 0.1379 0.2591 0.2045 0.026 Uiso 1 1 calc R U . . . C18 C 0.0983(4) 0.3250(3) 0.14255(18) 0.0246(11) Uani 1 1 d . . . . . C19 C 0.1422(3) 0.3631(2) 0.10141(17) 0.0225(10) Uani 1 1 d . . . . . H19 H 0.0965 0.3902 0.0778 0.027 Uiso 1 1 calc R U . . . C20 C 0.2500(4) 0.3625(2) 0.09419(16) 0.0184(10) Uani 1 1 d . . . . . C21 C 0.6096(4) 0.1928(2) 0.04916(17) 0.0260(11) Uani 1 1 d . . . . . H21A H 0.6868 0.1903 0.0461 0.039 Uiso 1 1 calc R U . . . H21B H 0.5774 0.2203 0.0198 0.039 Uiso 1 1 calc R U . . . H21C H 0.5811 0.1370 0.0514 0.039 Uiso 1 1 calc R U . . . C22 C 0.6224(4) 0.1923(3) 0.14252(17) 0.0262(11) Uani 1 1 d . . . . . H22A H 0.6030 0.2222 0.1726 0.039 Uiso 1 1 calc R U . . . H22B H 0.6998 0.1862 0.1424 0.039 Uiso 1 1 calc R U . . . H22C H 0.5891 0.1381 0.1423 0.039 Uiso 1 1 calc R U . . . C23 C 0.5773(4) 0.5220(3) 0.05870(16) 0.0230(10) Uani 1 1 d . . . . . H23A H 0.5053 0.5150 0.0706 0.035 Uiso 1 1 calc R U . . . H23B H 0.5938 0.4767 0.0363 0.035 Uiso 1 1 calc R U . . . H23C H 0.5817 0.5740 0.0406 0.035 Uiso 1 1 calc R U . . . C24 C 0.8629(3) 0.6645(2) 0.16119(18) 0.0259(11) Uani 1 1 d . . . . . H24A H 0.8978 0.6806 0.1307 0.039 Uiso 1 1 calc R U . . . H24B H 0.9169 0.6520 0.1874 0.039 Uiso 1 1 calc R U . . . H24C H 0.8178 0.7094 0.1722 0.039 Uiso 1 1 calc R U . . . C25 C 0.7474(3) 0.3801(2) 0.20727(16) 0.0196(10) Uani 1 1 d . . . . . H25A H 0.6797 0.3735 0.2237 0.029 Uiso 1 1 calc R U . . . H25B H 0.8044 0.3892 0.2325 0.029 Uiso 1 1 calc R U . . . H25C H 0.7624 0.3304 0.1882 0.029 Uiso 1 1 calc R U . . . C26 C 0.3474(3) 0.2354(2) 0.20614(16) 0.0211(10) Uani 1 1 d . . . . . H26A H 0.3771 0.1881 0.1890 0.032 Uiso 1 1 calc R U . . . H26B H 0.3069 0.2165 0.2344 0.032 Uiso 1 1 calc R U . . . H26C H 0.4052 0.2712 0.2183 0.032 Uiso 1 1 calc R U . . . C27 C -0.0189(4) 0.3263(3) 0.1493(2) 0.0405(14) Uani 1 1 d . . . . . H27A H -0.0427 0.3830 0.1532 0.061 Uiso 1 1 calc R U . . . H27B H -0.0354 0.2948 0.1791 0.061 Uiso 1 1 calc R U . . . H27C H -0.0555 0.3019 0.1200 0.061 Uiso 1 1 calc R U . . . C28 C 0.2960(3) 0.4014(2) 0.04884(16) 0.0231(10) Uani 1 1 d . . . . . H28A H 0.3454 0.4450 0.0594 0.035 Uiso 1 1 calc R U . . . H28B H 0.2385 0.4245 0.0276 0.035 Uiso 1 1 calc R U . . . H28C H 0.3340 0.3598 0.0301 0.035 Uiso 1 1 calc R U . . . C29 C 0.3007(3) 0.7415(2) 0.13929(15) 0.0131(9) Uani 1 1 d . . . . . C30 C 0.2378(3) 0.7495(2) 0.18029(15) 0.0165(9) Uani 1 1 d . . . . . C31 C 0.1732(3) 0.6837(2) 0.19218(16) 0.0172(9) Uani 1 1 d . . . . . H31 H 0.1290 0.6881 0.2200 0.021 Uiso 1 1 calc R U . . . C32 C 0.1715(3) 0.6117(2) 0.16441(16) 0.0174(9) Uani 1 1 d . . . . . C33 C 0.2334(3) 0.6082(2) 0.12280(16) 0.0184(10) Uani 1 1 d . . . . . H33 H 0.2321 0.5598 0.1031 0.022 Uiso 1 1 calc R U . . . C34 C 0.2974(3) 0.6732(2) 0.10880(15) 0.0160(9) Uani 1 1 d . . . . . C35 C 0.6504(3) 0.8728(2) 0.12279(16) 0.0151(9) Uani 1 1 d . . . . . C36 C 0.6982(3) 0.9137(2) 0.16352(16) 0.0173(10) Uani 1 1 d . . . . . C37 C 0.8083(4) 0.9134(2) 0.16714(18) 0.0252(11) Uani 1 1 d . . . . . H37 H 0.8432 0.9390 0.1950 0.030 Uiso 1 1 calc R U . . . C38 C 0.8693(4) 0.8767(3) 0.13112(19) 0.0249(11) Uani 1 1 d . . . . . C39 C 0.8177(3) 0.8410(3) 0.09000(17) 0.0236(11) Uani 1 1 d . . . . . H39 H 0.8586 0.8178 0.0645 0.028 Uiso 1 1 calc R U . . . C40 C 0.7083(3) 0.8382(2) 0.08525(17) 0.0193(10) Uani 1 1 d . . . . . C41 C 0.3474(4) 1.0073(3) 0.13789(16) 0.0255(11) Uani 1 1 d . . . . . H41A H 0.2701 1.0129 0.1391 0.038 Uiso 1 1 calc R U . . . H41B H 0.3795 1.0615 0.1342 0.038 Uiso 1 1 calc R U . . . H41C H 0.3751 0.9820 0.1689 0.038 Uiso 1 1 calc R U . . . C42 C 0.3389(4) 0.9950(2) 0.04406(16) 0.0221(10) Uani 1 1 d . . . . . H42A H 0.3631 0.9633 0.0156 0.033 Uiso 1 1 calc R U . . . H42B H 0.3691 1.0503 0.0431 0.033 Uiso 1 1 calc R U . . . H42C H 0.2612 0.9985 0.0423 0.033 Uiso 1 1 calc R U . . . C43 C 0.2417(3) 0.8246(2) 0.21285(16) 0.0218(10) Uani 1 1 d . . . . . H43A H 0.3148 0.8338 0.2254 0.033 Uiso 1 1 calc R U . . . H43B H 0.1956 0.8166 0.2411 0.033 Uiso 1 1 calc R U . . . H43C H 0.2172 0.8722 0.1933 0.033 Uiso 1 1 calc R U . . . C44 C 0.1057(3) 0.5386(2) 0.17920(17) 0.0246(11) Uani 1 1 d . . . . . H44A H 0.0586 0.5223 0.1510 0.037 Uiso 1 1 calc R U . . . H44B H 0.0631 0.5533 0.2077 0.037 Uiso 1 1 calc R U . . . H44C H 0.1529 0.4929 0.1885 0.037 Uiso 1 1 calc R U . . . C45 C 0.3579(4) 0.6694(3) 0.06160(16) 0.0249(11) Uani 1 1 d . . . . . H45A H 0.3530 0.6140 0.0476 0.037 Uiso 1 1 calc R U . . . H45B H 0.4326 0.6830 0.0690 0.037 Uiso 1 1 calc R U . . . H45C H 0.3276 0.7087 0.0374 0.037 Uiso 1 1 calc R U . . . C46 C 0.6329(3) 0.9573(2) 0.20092(16) 0.0251(11) Uani 1 1 d . . . . . H46A H 0.6795 0.9782 0.2281 0.038 Uiso 1 1 calc R U . . . H46B H 0.5814 0.9190 0.2144 0.038 Uiso 1 1 calc R U . . . H46C H 0.5951 1.0031 0.1846 0.038 Uiso 1 1 calc R U . . . C47 C 0.9885(4) 0.8739(3) 0.1373(2) 0.0381(14) Uani 1 1 d . . . . . H47A H 1.0100 0.8233 0.1546 0.057 Uiso 1 1 calc R U . . . H47B H 1.0134 0.9212 0.1571 0.057 Uiso 1 1 calc R U . . . H47C H 1.0198 0.8755 0.1044 0.057 Uiso 1 1 calc R U . . . C48 C 0.6539(3) 0.8002(3) 0.04014(16) 0.0248(11) Uani 1 1 d . . . . . H48A H 0.6109 0.8417 0.0223 0.037 Uiso 1 1 calc R U . . . H48B H 0.6079 0.7554 0.0506 0.037 Uiso 1 1 calc R U . . . H48C H 0.7073 0.7786 0.0180 0.037 Uiso 1 1 calc R U . . . C1S C 0.0549(5) 0.8123(3) -0.0122(2) 0.0563(18) Uani 1 1 d . . . . . H1S H 0.0942 0.7745 0.0081 0.068 Uiso 1 1 calc R U . . . C2S C -0.0456(4) 0.7930(3) -0.0297(2) 0.0460(15) Uani 1 1 d . . . . . H2S H -0.0755 0.7415 -0.0215 0.055 Uiso 1 1 calc R U . . . C3S C -0.1035(4) 0.8471(3) -0.05864(19) 0.0427(14) Uani 1 1 d . . . . . H3S H -0.1731 0.8334 -0.0708 0.051 Uiso 1 1 calc R U . . . C4S C -0.0596(4) 0.9211(4) -0.0698(2) 0.0550(17) Uani 1 1 d . . . . . H4S H -0.0996 0.9590 -0.0898 0.066 Uiso 1 1 calc R U . . . C5S C 0.0416(5) 0.9419(4) -0.0527(2) 0.0523(16) Uani 1 1 d . . . . . H5S H 0.0709 0.9938 -0.0606 0.063 Uiso 1 1 calc R U . . . C6S C 0.0988(4) 0.8867(4) -0.0242(2) 0.0498(16) Uani 1 1 d . . . . . H6S H 0.1690 0.8997 -0.0127 0.060 Uiso 1 1 calc R U . . . C7S C 0.0973(10) 0.0905(6) 0.2533(5) 0.048(3) Uani 0.5 1 d G . P A -1 H7S H 0.1710 0.0860 0.2617 0.058 Uiso 0.5 1 calc R U P A -1 C12S C 0.0629(10) 0.0976(6) 0.2036(5) 0.048(3) Uani 0.5 1 d G . P A -1 H12S H 0.1131 0.0980 0.1780 0.058 Uiso 0.5 1 calc R U P A -1 C11S C -0.0449(11) 0.1041(6) 0.1913(4) 0.048(3) Uani 0.5 1 d G . P A -1 H11S H -0.0684 0.1089 0.1573 0.058 Uiso 0.5 1 calc R U P A -1 C10S C -0.1183(10) 0.1035(6) 0.2286(5) 0.048(3) Uani 0.5 1 d G . P A -1 H10S H -0.1920 0.1079 0.2202 0.058 Uiso 0.5 1 calc R U P A -1 C9S C -0.0840(11) 0.0964(5) 0.2783(4) 0.048(3) Uani 0.5 1 d G . P A -1 H9S H -0.1342 0.0960 0.3039 0.058 Uiso 0.5 1 calc R U P A -1 C8S C 0.0239(11) 0.0899(6) 0.2907(4) 0.048(3) Uani 0.5 1 d G . P A -1 H8S H 0.0474 0.0850 0.3246 0.058 Uiso 0.5 1 calc R U P A -1 C13S C -0.0054(6) 0.5579(4) 0.0361(2) 0.0554(19) Uani 1 1 d . . . . . H13S H -0.0099 0.5988 0.0612 0.066 Uiso 1 1 calc R U . . . C14S C 0.0686(5) 0.5648(3) 0.0001(3) 0.0511(16) Uani 1 1 d . . . . . H14S H 0.1166 0.6097 0.0009 0.061 Uiso 1 1 calc R U . . . C15S C 0.0735(5) 0.5085(4) -0.0361(2) 0.0531(17) Uani 1 1 d . . . . . H15S H 0.1235 0.5141 -0.0615 0.064 Uiso 1 1 calc R U . . . 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 0.0131(6) 0.0124(5) 0.0174(6) -0.0031(4) 0.0016(5) -0.0007(5) P2 0.0112(6) 0.0118(5) 0.0141(5) -0.0008(4) 0.0018(4) 0.0008(4) P3 0.0123(6) 0.0109(5) 0.0152(6) 0.0007(4) 0.0000(4) -0.0002(4) P4 0.0125(6) 0.0132(5) 0.0196(6) 0.0040(4) 0.0001(5) -0.0011(5) O1 0.0205(18) 0.0199(15) 0.036(2) -0.0068(14) 0.0103(15) -0.0015(14) O2 0.0219(18) 0.0149(14) 0.0285(18) -0.0080(13) 0.0005(14) -0.0041(13) O3 0.0165(18) 0.0251(17) 0.038(2) 0.0117(14) -0.0089(15) -0.0033(14) O4 0.0198(19) 0.0221(16) 0.038(2) 0.0138(14) 0.0039(15) -0.0036(14) N1 0.012(2) 0.0131(16) 0.0166(19) -0.0026(14) 0.0008(15) 0.0005(15) N2 0.0102(19) 0.0114(16) 0.0142(18) -0.0008(13) 0.0007(14) -0.0020(14) N3 0.014(2) 0.0117(16) 0.019(2) 0.0046(14) -0.0019(15) -0.0004(15) N4 0.0110(19) 0.0141(16) 0.0198(19) 0.0058(14) -0.0027(16) -0.0027(15) C1 0.013(2) 0.0125(19) 0.016(2) 0.0017(16) -0.0019(18) -0.0032(17) C2 0.018(2) 0.015(2) 0.018(2) -0.0018(17) 0.0017(19) 0.0045(18) C3 0.016(2) 0.0107(19) 0.021(2) -0.0017(17) 0.0037(19) -0.0001(18) C4 0.020(2) 0.014(2) 0.013(2) 0.0020(17) 0.0033(18) 0.0015(19) C5 0.012(2) 0.0114(19) 0.016(2) -0.0045(17) 0.0038(17) -0.0010(17) C6 0.014(2) 0.014(2) 0.016(2) -0.0024(17) 0.0051(18) 0.0030(17) C7 0.018(2) 0.014(2) 0.020(2) 0.0035(17) 0.0069(19) 0.0022(18) C8 0.011(2) 0.015(2) 0.027(3) -0.0045(18) 0.0052(19) -0.0012(18) C9 0.012(2) 0.021(2) 0.018(2) -0.0041(18) 0.0003(18) 0.0015(18) C10 0.012(2) 0.016(2) 0.015(2) 0.0005(17) 0.0058(17) 0.0052(18) C11 0.012(2) 0.015(2) 0.015(2) -0.0013(16) 0.0029(18) -0.0006(18) C12 0.018(3) 0.018(2) 0.020(2) 0.0038(18) 0.000(2) 0.0012(19) C13 0.014(2) 0.012(2) 0.022(2) 0.0012(17) -0.0012(18) -0.0003(18) C14 0.023(3) 0.018(2) 0.016(2) 0.0036(17) -0.0002(19) -0.002(2) C15 0.009(2) 0.012(2) 0.025(3) -0.0074(17) 0.0009(19) -0.0018(17) C16 0.020(2) 0.010(2) 0.019(2) -0.0048(17) 0.0036(19) -0.0048(18) C17 0.022(3) 0.018(2) 0.026(3) -0.0033(19) 0.009(2) -0.006(2) C18 0.018(3) 0.020(2) 0.036(3) -0.007(2) 0.005(2) -0.005(2) C19 0.013(2) 0.018(2) 0.036(3) -0.007(2) -0.004(2) 0.0009(19) C20 0.018(3) 0.012(2) 0.026(3) -0.0043(18) -0.004(2) -0.0015(18) C21 0.029(3) 0.017(2) 0.032(3) -0.008(2) 0.010(2) -0.002(2) C22 0.025(3) 0.020(2) 0.034(3) 0.009(2) -0.001(2) 0.001(2) C23 0.024(3) 0.023(2) 0.021(3) 0.0039(18) 0.000(2) -0.004(2) C24 0.021(3) 0.020(2) 0.037(3) -0.006(2) 0.002(2) -0.004(2) C25 0.016(2) 0.021(2) 0.022(3) 0.0030(19) 0.0021(19) 0.0015(19) C26 0.024(3) 0.020(2) 0.020(2) 0.0013(19) 0.0040(19) -0.003(2) C27 0.018(3) 0.039(3) 0.065(4) 0.000(3) 0.010(3) 0.001(2) C28 0.024(3) 0.021(2) 0.023(3) 0.0003(19) -0.003(2) 0.001(2) C29 0.011(2) 0.012(2) 0.016(2) 0.0042(17) -0.0030(17) -0.0012(17) C30 0.012(2) 0.016(2) 0.021(2) 0.0029(18) -0.0055(18) -0.0007(18) C31 0.011(2) 0.021(2) 0.020(2) 0.0025(18) 0.0007(18) -0.0008(18) C32 0.010(2) 0.022(2) 0.020(2) 0.0045(18) -0.0022(18) -0.0004(18) C33 0.014(2) 0.016(2) 0.025(3) 0.0004(18) -0.0064(19) -0.0020(18) C34 0.015(2) 0.017(2) 0.015(2) 0.0027(17) -0.0023(18) 0.0027(18) C35 0.010(2) 0.016(2) 0.019(2) 0.0073(18) 0.0004(19) -0.0036(18) C36 0.018(3) 0.013(2) 0.021(2) 0.0071(18) 0.0011(19) -0.0018(18) C37 0.021(3) 0.018(2) 0.037(3) 0.007(2) -0.007(2) -0.008(2) C38 0.015(3) 0.019(2) 0.040(3) 0.008(2) -0.004(2) -0.005(2) C39 0.018(3) 0.023(2) 0.030(3) 0.009(2) 0.005(2) -0.002(2) C40 0.018(3) 0.015(2) 0.025(3) 0.0072(18) 0.0033(19) -0.0050(19) C41 0.030(3) 0.022(2) 0.025(3) -0.0021(19) 0.001(2) 0.002(2) C42 0.022(3) 0.019(2) 0.025(3) 0.0077(19) -0.004(2) 0.002(2) C43 0.018(2) 0.022(2) 0.026(3) -0.0015(19) 0.003(2) 0.0003(19) C44 0.021(3) 0.020(2) 0.033(3) 0.005(2) 0.003(2) -0.007(2) C45 0.028(3) 0.023(2) 0.024(3) -0.0014(19) 0.004(2) -0.005(2) C46 0.027(3) 0.019(2) 0.028(3) 0.000(2) -0.006(2) -0.001(2) C47 0.017(3) 0.037(3) 0.060(4) 0.007(3) -0.001(3) -0.006(2) C48 0.024(3) 0.028(2) 0.023(3) 0.001(2) 0.006(2) 0.000(2) C1S 0.057(4) 0.033(3) 0.076(5) -0.012(3) -0.027(4) 0.008(3) C2S 0.047(4) 0.037(3) 0.053(4) -0.016(3) -0.011(3) 0.001(3) C3S 0.028(3) 0.066(4) 0.034(3) -0.006(3) -0.001(2) 0.000(3) C4S 0.026(3) 0.083(5) 0.056(4) 0.026(3) -0.002(3) -0.001(3) C5S 0.036(4) 0.057(4) 0.063(4) 0.017(3) -0.004(3) -0.003(3) C6S 0.034(4) 0.054(4) 0.060(4) -0.022(3) -0.014(3) 0.008(3) C7S 0.056(5) 0.023(2) 0.066(8) 0.001(2) 0.007(5) 0.000(3) C12S 0.056(5) 0.023(2) 0.066(8) 0.001(2) 0.007(5) 0.000(3) C11S 0.056(5) 0.023(2) 0.066(8) 0.001(2) 0.007(5) 0.000(3) C10S 0.056(5) 0.023(2) 0.066(8) 0.001(2) 0.007(5) 0.000(3) C9S 0.056(5) 0.023(2) 0.066(8) 0.001(2) 0.007(5) 0.000(3) C8S 0.056(5) 0.023(2) 0.066(8) 0.001(2) 0.007(5) 0.000(3) C13S 0.076(5) 0.058(4) 0.029(3) -0.017(3) -0.022(3) 0.042(4) C14S 0.036(4) 0.047(3) 0.068(5) 0.010(3) -0.026(3) 0.006(3) C15S 0.038(4) 0.081(5) 0.041(4) 0.020(3) 0.009(3) 0.037(4) _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 C1 1.738(4) . ? P1 P2 2.2056(15) . ? P2 P2 2.252(2) 2_655 ? P2 P3 2.2628(14) . ? P3 P4 2.2128(15) . ? P3 P3 2.258(2) 2_655 ? P4 C11 1.737(4) . ? O1 C2 1.201(5) . ? O2 C4 1.214(5) . ? O3 C12 1.199(5) . ? O4 C14 1.222(5) . ? N1 C1 1.390(5) . ? N1 C2 1.410(5) . ? N1 C5 1.462(5) . ? N2 C4 1.392(5) . ? N2 C1 1.420(5) . ? N2 C15 1.440(5) . ? N3 C11 1.393(5) . ? N3 C12 1.403(5) . ? N3 C29 1.458(5) . ? N4 C14 1.380(5) . ? N4 C11 1.424(5) . ? N4 C35 1.448(5) . ? C2 C3 1.521(5) . ? C3 C4 1.510(5) . ? C3 C21 1.520(6) . ? C3 C22 1.537(6) . ? C5 C10 1.381(5) . ? C5 C6 1.389(5) . ? C6 C7 1.388(5) . ? C6 C23 1.490(6) . ? C7 C8 1.386(6) . ? C7 H7 0.9500 . ? C8 C9 1.382(6) . ? C8 C24 1.508(5) . ? C9 C10 1.386(5) . ? C9 H9 0.9500 . ? C10 C25 1.495(5) . ? C12 C13 1.516(6) . ? C13 C14 1.495(6) . ? C13 C42 1.534(6) . ? C13 C41 1.552(6) . ? C15 C16 1.393(6) . ? C15 C20 1.395(6) . ? C16 C17 1.386(5) . ? C16 C26 1.502(6) . ? C17 C18 1.387(6) . ? C17 H17 0.9500 . ? C18 C19 1.399(6) . ? C18 C27 1.495(6) . ? C19 C20 1.379(5) . ? C19 H19 0.9500 . ? C20 C28 1.507(6) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 C34 1.382(5) . ? C29 C30 1.386(5) . ? C30 C31 1.392(5) . ? C30 C43 1.504(5) . ? C31 C32 1.391(5) . ? C31 H31 0.9500 . ? C32 C33 1.387(6) . ? C32 C44 1.514(5) . ? C33 C34 1.393(5) . ? C33 H33 0.9500 . ? C34 C45 1.503(6) . ? C35 C40 1.386(6) . ? C35 C36 1.396(6) . ? C36 C37 1.387(6) . ? C36 C46 1.501(6) . ? C37 C38 1.393(6) . ? C37 H37 0.9500 . ? C38 C39 1.386(6) . ? C38 C47 1.507(6) . ? C39 C40 1.380(5) . ? C39 H39 0.9500 . ? C40 C48 1.501(6) . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C48 H48C 0.9800 . ? C1S C2S 1.369(7) . ? C1S C6S 1.377(8) . ? C1S H1S 0.9500 . ? C2S C3S 1.368(7) . ? C2S H2S 0.9500 . ? C3S C4S 1.366(7) . ? C3S H3S 0.9500 . ? C4S C5S 1.381(7) . ? C4S H4S 0.9500 . ? C5S C6S 1.369(7) . ? C5S H5S 0.9500 . ? C6S H6S 0.9500 . ? C7S C12S 1.3900 . ? C7S C8S 1.3900 . ? C7S H7S 0.9500 . ? C12S C11S 1.3900 . ? C12S H12S 0.9500 . ? C11S C10S 1.3900 . ? C11S H11S 0.9500 . ? C10S C9S 1.3900 . ? C10S H10S 0.9500 . ? C9S C8S 1.3900 . ? C9S H9S 0.9500 . ? C8S H8S 0.9500 . ? C13S C14S 1.373(8) . ? C13S C15S 1.381(8) 3_565 ? C13S H13S 0.9500 . ? C14S C15S 1.339(8) . ? C14S H14S 0.9500 . ? C15S C13S 1.381(8) 3_565 ? C15S H15S 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 P1 P2 107.69(14) . . ? P1 P2 P2 94.18(6) . 2_655 ? P1 P2 P3 102.54(6) . . ? P2 P2 P3 75.34(4) 2_655 . ? P4 P3 P3 94.66(6) . 2_655 ? P4 P3 P2 101.63(6) . . ? P3 P3 P2 75.22(4) 2_655 . ? C11 P4 P3 107.89(14) . . ? C1 N1 C2 125.5(3) . . ? C1 N1 C5 120.2(3) . . ? C2 N1 C5 114.1(3) . . ? C4 N2 C1 126.1(3) . . ? C4 N2 C15 115.5(3) . . ? C1 N2 C15 118.3(3) . . ? C11 N3 C12 124.6(3) . . ? C11 N3 C29 120.9(3) . . ? C12 N3 C29 114.4(3) . . ? C14 N4 C11 126.1(3) . . ? C14 N4 C35 114.8(3) . . ? C11 N4 C35 118.9(3) . . ? N1 C1 N2 113.9(3) . . ? N1 C1 P1 132.4(3) . . ? N2 C1 P1 113.6(3) . . ? O1 C2 N1 120.5(4) . . ? O1 C2 C3 122.9(4) . . ? N1 C2 C3 116.4(4) . . ? C4 C3 C21 109.9(3) . . ? C4 C3 C2 111.8(3) . . ? C21 C3 C2 110.4(3) . . ? C4 C3 C22 107.4(3) . . ? C21 C3 C22 109.8(3) . . ? C2 C3 C22 107.4(3) . . ? O2 C4 N2 120.5(4) . . ? O2 C4 C3 122.0(4) . . ? N2 C4 C3 117.4(3) . . ? C10 C5 C6 122.9(4) . . ? C10 C5 N1 118.0(3) . . ? C6 C5 N1 119.0(4) . . ? C7 C6 C5 117.5(4) . . ? C7 C6 C23 121.2(4) . . ? C5 C6 C23 121.2(4) . . ? C8 C7 C6 121.7(4) . . ? C8 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? C9 C8 C7 118.0(4) . . ? C9 C8 C24 121.8(4) . . ? C7 C8 C24 120.1(4) . . ? C8 C9 C10 122.7(4) . . ? C8 C9 H9 118.7 . . ? C10 C9 H9 118.7 . . ? C5 C10 C9 117.0(4) . . ? C5 C10 C25 121.6(4) . . ? C9 C10 C25 121.3(4) . . ? N3 C11 N4 114.4(3) . . ? N3 C11 P4 132.1(3) . . ? N4 C11 P4 113.5(3) . . ? O3 C12 N3 119.6(4) . . ? O3 C12 C13 122.6(4) . . ? N3 C12 C13 117.6(4) . . ? C14 C13 C12 113.0(3) . . ? C14 C13 C42 109.6(4) . . ? C12 C13 C42 110.6(3) . . ? C14 C13 C41 107.3(3) . . ? C12 C13 C41 106.7(3) . . ? C42 C13 C41 109.6(3) . . ? O4 C14 N4 120.1(4) . . ? O4 C14 C13 122.0(4) . . ? N4 C14 C13 117.8(4) . . ? C16 C15 C20 122.0(4) . . ? C16 C15 N2 119.5(4) . . ? C20 C15 N2 118.4(4) . . ? C17 C16 C15 117.8(4) . . ? C17 C16 C26 121.4(4) . . ? C15 C16 C26 120.8(4) . . ? C16 C17 C18 122.2(4) . . ? C16 C17 H17 118.9 . . ? C18 C17 H17 118.9 . . ? C17 C18 C19 118.0(4) . . ? C17 C18 C27 121.2(4) . . ? C19 C18 C27 120.8(4) . . ? C20 C19 C18 121.9(4) . . ? C20 C19 H19 119.0 . . ? C18 C19 H19 119.0 . . ? C19 C20 C15 118.0(4) . . ? C19 C20 C28 121.4(4) . . ? C15 C20 C28 120.5(4) . . ? C3 C21 H21A 109.5 . . ? C3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C3 C22 H22A 109.5 . . ? C3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C6 C23 H23A 109.5 . . ? C6 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C6 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C8 C24 H24A 109.5 . . ? C8 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C8 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C10 C25 H25A 109.5 . . ? C10 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C10 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C16 C26 H26A 109.5 . . ? C16 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C16 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C18 C27 H27A 109.5 . . ? C18 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C18 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C20 C28 H28A 109.5 . . ? C20 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C20 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C34 C29 C30 122.7(4) . . ? C34 C29 N3 119.2(4) . . ? C30 C29 N3 118.0(3) . . ? C29 C30 C31 117.8(4) . . ? C29 C30 C43 122.0(4) . . ? C31 C30 C43 120.1(4) . . ? C32 C31 C30 121.7(4) . . ? C32 C31 H31 119.1 . . ? C30 C31 H31 119.1 . . ? C33 C32 C31 117.9(4) . . ? C33 C32 C44 120.6(4) . . ? C31 C32 C44 121.5(4) . . ? C32 C33 C34 122.3(4) . . ? C32 C33 H33 118.8 . . ? C34 C33 H33 118.8 . . ? C29 C34 C33 117.3(4) . . ? C29 C34 C45 121.8(4) . . ? C33 C34 C45 120.9(4) . . ? C40 C35 C36 122.6(4) . . ? C40 C35 N4 118.9(4) . . ? C36 C35 N4 118.2(4) . . ? C37 C36 C35 116.9(4) . . ? C37 C36 C46 121.9(4) . . ? C35 C36 C46 121.2(4) . . ? C36 C37 C38 122.0(4) . . ? C36 C37 H37 119.0 . . ? C38 C37 H37 119.0 . . ? C39 C38 C37 118.5(4) . . ? C39 C38 C47 120.7(4) . . ? C37 C38 C47 120.7(4) . . ? C40 C39 C38 121.5(4) . . ? C40 C39 H39 119.2 . . ? C38 C39 H39 119.2 . . ? C39 C40 C35 118.1(4) . . ? C39 C40 C48 120.7(4) . . ? C35 C40 C48 121.1(4) . . ? C13 C41 H41A 109.5 . . ? C13 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C13 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C13 C42 H42A 109.5 . . ? C13 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C13 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C30 C43 H43A 109.5 . . ? C30 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C30 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C32 C44 H44A 109.5 . . ? C32 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C32 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C34 C45 H45A 109.5 . . ? C34 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C34 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C36 C46 H46A 109.5 . . ? C36 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C36 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C38 C47 H47A 109.5 . . ? C38 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C38 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C40 C48 H48A 109.5 . . ? C40 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C40 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C2S C1S C6S 119.9(5) . . ? C2S C1S H1S 120.1 . . ? C6S C1S H1S 120.1 . . ? C3S C2S C1S 120.7(5) . . ? C3S C2S H2S 119.6 . . ? C1S C2S H2S 119.6 . . ? C4S C3S C2S 118.9(5) . . ? C4S C3S H3S 120.6 . . ? C2S C3S H3S 120.6 . . ? C3S C4S C5S 121.5(5) . . ? C3S C4S H4S 119.3 . . ? C5S C4S H4S 119.3 . . ? C6S C5S C4S 118.9(5) . . ? C6S C5S H5S 120.6 . . ? C4S C5S H5S 120.6 . . ? C5S C6S C1S 120.2(5) . . ? C5S C6S H6S 119.9 . . ? C1S C6S H6S 119.9 . . ? C12S C7S C8S 120.0 . . ? C12S C7S H7S 120.0 . . ? C8S C7S H7S 120.0 . . ? C7S C12S C11S 120.0 . . ? C7S C12S H12S 120.0 . . ? C11S C12S H12S 120.0 . . ? C12S C11S C10S 120.0 . . ? C12S C11S H11S 120.0 . . ? C10S C11S H11S 120.0 . . ? C9S C10S C11S 120.0 . . ? C9S C10S H10S 120.0 . . ? C11S C10S H10S 120.0 . . ? C10S C9S C8S 120.0 . . ? C10S C9S H9S 120.0 . . ? C8S C9S H9S 120.0 . . ? C9S C8S C7S 120.0 . . ? C9S C8S H8S 120.0 . . ? C7S C8S H8S 120.0 . . ? C14S C13S C15S 120.2(5) . 3_565 ? C14S C13S H13S 119.9 . . ? C15S C13S H13S 119.9 3_565 . ? C15S C14S C13S 120.3(6) . . ? C15S C14S H14S 119.9 . . ? C13S C14S H14S 119.9 . . ? C14S C15S C13S 119.5(6) . 3_565 ? C14S C15S H15S 120.2 . . ? C13S C15S H15S 120.2 3_565 . ? _refine_diff_density_max 0.439 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.085 data_gbcm2 _database_code_depnum_ccdc_archive 'CCDC 930072' #TrackingRef '18671_web_deposit_cif_file_1_CalebMartin_1363713550.3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C92 H140 N4 P8, C6 H6' _chemical_formula_sum 'C98 H146 N4 P8' _chemical_formula_weight 1628.0482 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fddd _symmetry_space_group_name_Hall '-F 2uv 2vw' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y+1/4, -z+1/4' '-x+1/4, y, -z+1/4' '-x+1/4, -y+1/4, z' 'x, y+1/2, z+1/2' 'x, -y+3/4, -z+3/4' '-x+1/4, y+1/2, -z+3/4' '-x+1/4, -y+3/4, z+1/2' 'x+1/2, y, z+1/2' 'x+1/2, -y+1/4, -z+3/4' '-x+3/4, y, -z+3/4' '-x+3/4, -y+1/4, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+3/4, -z+1/4' '-x+3/4, y+1/2, -z+1/4' '-x+3/4, -y+3/4, z' '-x, -y, -z' '-x, y-1/4, z-1/4' 'x-1/4, -y, z-1/4' 'x-1/4, y-1/4, -z' '-x, -y+1/2, -z+1/2' '-x, y+1/4, z+1/4' 'x-1/4, -y+1/2, z+1/4' 'x-1/4, y+1/4, -z+1/2' '-x+1/2, -y, -z+1/2' '-x+1/2, y-1/4, z+1/4' 'x+1/4, -y, z+1/4' 'x+1/4, y-1/4, -z+1/2' '-x+1/2, -y+1/2, -z' '-x+1/2, y+1/4, z-1/4' 'x+1/4, -y+1/2, z-1/4' 'x+1/4, y+1/4, -z' _cell_length_a 12.0923(12) _cell_length_b 29.578(3) _cell_length_c 53.934(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 19290(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 50814 _cell_measurement_theta_min 1.51 _cell_measurement_theta_max 26.48 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.121 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 7056 _exptl_absorpt_coefficient_mu 0.190 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9721 _exptl_absorpt_correction_T_max 0.9776 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean '512 x 512' _diffrn_reflns_number 48349 _diffrn_reflns_av_R_equivalents 0.1266 _diffrn_reflns_av_sigmaI/netI 0.0652 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -67 _diffrn_reflns_limit_l_max 67 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 26.44 _reflns_number_total 4945 _reflns_number_gt 3539 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'BRUKER SHELXTL' _computing_publication_material 'BRUKER SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0368P)^2^+45.6038P] 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 4945 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0756 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1067 _refine_ls_wR_factor_gt 0.0934 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 N1 N 0.77547(13) 0.50309(5) 0.05021(3) 0.0134(4) Uani 1 1 d . . . P2 P 0.59718(4) 0.588994(17) 0.105030(9) 0.01428(14) Uani 1 1 d . . . P1 P 0.74554(5) 0.565335(19) 0.085373(10) 0.01893(15) Uani 1 1 d . . . C21 C 0.88358(16) 0.52269(7) 0.04653(4) 0.0148(4) Uani 1 1 d . . . C26A C 0.9877(2) 0.49118(9) 0.10600(4) 0.0362(6) Uani 1 1 d . . . H26A H 0.9408 0.5177 0.1088 0.054 Uiso 1 1 calc R . . H26B H 1.0656 0.5003 0.1063 0.054 Uiso 1 1 calc R . . H26C H 0.9741 0.4688 0.1190 0.054 Uiso 1 1 calc R . . C1 C 0.70377(16) 0.51952(6) 0.06752(4) 0.0134(4) Uani 1 1 d . . . C22A C 0.7859(2) 0.63004(7) 0.02666(5) 0.0318(6) Uani 1 1 d . . . H22A H 0.7761 0.6291 0.0447 0.048 Uiso 1 1 calc R . . H22B H 0.7202 0.6435 0.0190 0.048 Uiso 1 1 calc R . . H22C H 0.8511 0.6483 0.0226 0.048 Uiso 1 1 calc R . . C14 C 0.39513(18) 0.48834(8) 0.05533(4) 0.0278(5) Uani 1 1 d . . . H14A H 0.3336 0.5071 0.0489 0.033 Uiso 1 1 calc R . . H14B H 0.4046 0.4622 0.0441 0.033 Uiso 1 1 calc R . . C26 C 0.97296(17) 0.50576(7) 0.06044(4) 0.0189(5) Uani 1 1 d . . . C22C C 0.8172(2) 0.58270(8) -0.01137(4) 0.0341(6) Uani 1 1 d . . . H22D H 0.8274 0.5517 -0.0174 0.051 Uiso 1 1 calc R . . H22E H 0.8825 0.6008 -0.0155 0.051 Uiso 1 1 calc R . . H22F H 0.7517 0.5960 -0.0192 0.051 Uiso 1 1 calc R . . C12 C 0.46237(19) 0.44542(8) 0.09259(4) 0.0278(5) Uani 1 1 d . . . H12A H 0.4426 0.4362 0.1097 0.033 Uiso 1 1 calc R . . H12B H 0.4765 0.4177 0.0828 0.033 Uiso 1 1 calc R . . C26C C 1.0337(2) 0.42894(8) 0.07627(5) 0.0335(6) Uani 1 1 d . . . H26D H 1.0162 0.4157 0.0601 0.050 Uiso 1 1 calc R . . H26E H 1.0202 0.4065 0.0893 0.050 Uiso 1 1 calc R . . H26F H 1.1117 0.4380 0.0766 0.050 Uiso 1 1 calc R . . C24 C 1.09242(19) 0.55886(8) 0.03960(4) 0.0280(5) Uani 1 1 d . . . H24A H 1.1644 0.5707 0.0368 0.034 Uiso 1 1 calc R . . C13 C 0.36635(19) 0.47142(9) 0.08114(5) 0.0335(6) Uani 1 1 d . . . H13A H 0.3007 0.4515 0.0802 0.040 Uiso 1 1 calc R . . H13B H 0.3475 0.4975 0.0919 0.040 Uiso 1 1 calc R . . C26B C 0.96040(19) 0.47050(8) 0.08071(4) 0.0241(5) Uani 1 1 d . . . H26G H 0.8815 0.4603 0.0810 0.029 Uiso 1 1 calc R . . C11 C 0.56654(17) 0.47418(7) 0.09324(4) 0.0174(4) Uani 1 1 d . . . H11A H 0.6279 0.4563 0.1004 0.021 Uiso 1 1 calc R . . H11B H 0.5540 0.5008 0.1040 0.021 Uiso 1 1 calc R . . C22 C 0.89680(18) 0.55899(7) 0.03001(4) 0.0182(5) Uani 1 1 d . . . C4 C 0.73252(17) 0.46480(7) 0.03502(4) 0.0168(4) Uani 1 1 d . . . C22B C 0.80176(19) 0.58203(7) 0.01679(4) 0.0224(5) Uani 1 1 d . . . H22G H 0.7329 0.5646 0.0205 0.027 Uiso 1 1 calc R . . C23 C 1.00367(19) 0.57612(7) 0.02682(4) 0.0239(5) Uani 1 1 d . . . H23A H 1.0152 0.6003 0.0155 0.029 Uiso 1 1 calc R . . C6 C 0.69594(19) 0.48019(7) 0.00922(4) 0.0231(5) Uani 1 1 d . . . H6A H 0.7608 0.4896 -0.0004 0.035 Uiso 1 1 calc R . . H6B H 0.6447 0.5057 0.0108 0.035 Uiso 1 1 calc R . . H6C H 0.6589 0.4551 0.0007 0.035 Uiso 1 1 calc R . . C2 C 0.59931(16) 0.49028(6) 0.06716(4) 0.0136(4) Uani 1 1 d . . . C3 C 0.63513(17) 0.44957(7) 0.05108(4) 0.0174(5) Uani 1 1 d . . . H3A H 0.6575 0.4240 0.0618 0.021 Uiso 1 1 calc R . . H3B H 0.5730 0.4396 0.0405 0.021 Uiso 1 1 calc R . . C25 C 1.07707(18) 0.52447(8) 0.05640(4) 0.0252(5) Uani 1 1 d . . . H25A H 1.1387 0.5132 0.0654 0.030 Uiso 1 1 calc R . . C15 C 0.50108(16) 0.51625(7) 0.05566(4) 0.0178(5) Uani 1 1 d . . . H15A H 0.4882 0.5443 0.0653 0.021 Uiso 1 1 calc R . . H15B H 0.5202 0.5251 0.0385 0.021 Uiso 1 1 calc R . . C5 C 0.81885(18) 0.42802(7) 0.03197(4) 0.0242(5) Uani 1 1 d . . . H5A H 0.8794 0.4392 0.0216 0.036 Uiso 1 1 calc R . . H5B H 0.7851 0.4016 0.0241 0.036 Uiso 1 1 calc R . . H5C H 0.8478 0.4195 0.0483 0.036 Uiso 1 1 calc R . . C101 C 0.7388(5) 0.1250 0.1250 0.0739(15) Uani 1 2 d S . . H10A H 0.8173 0.1250 0.1250 0.089 Uiso 1 2 calc SR . . C100 C 0.6826(3) 0.12503(14) 0.10304(7) 0.0776(11) Uani 1 1 d . . . H10B H 0.7219 0.1251 0.0878 0.093 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 N1 0.0138(9) 0.0130(8) 0.0135(9) -0.0031(6) 0.0027(7) -0.0026(7) P2 0.0156(3) 0.0152(3) 0.0120(3) -0.0022(2) 0.0021(2) -0.0009(2) P1 0.0165(3) 0.0214(3) 0.0188(3) -0.0092(2) 0.0060(2) -0.0054(2) C21 0.0135(10) 0.0173(10) 0.0134(10) -0.0061(8) 0.0054(8) -0.0019(8) C26A 0.0333(14) 0.0502(16) 0.0250(14) 0.0047(12) -0.0066(11) -0.0012(13) C1 0.0136(10) 0.0155(10) 0.0110(10) 0.0011(8) 0.0007(8) -0.0001(8) C22A 0.0353(14) 0.0200(12) 0.0401(15) 0.0041(10) 0.0078(12) -0.0007(11) C14 0.0140(11) 0.0410(14) 0.0284(13) -0.0017(11) -0.0036(10) -0.0015(10) C26 0.0168(11) 0.0217(11) 0.0181(11) -0.0050(9) 0.0045(9) -0.0012(9) C22C 0.0430(16) 0.0335(14) 0.0259(14) 0.0078(11) -0.0011(11) -0.0111(12) C12 0.0255(12) 0.0289(13) 0.0291(13) 0.0053(10) 0.0074(10) -0.0077(10) C26C 0.0216(12) 0.0373(14) 0.0418(16) 0.0074(12) 0.0015(11) 0.0056(11) C24 0.0183(12) 0.0307(13) 0.0349(14) -0.0046(11) 0.0108(10) -0.0088(10) C13 0.0152(11) 0.0484(16) 0.0369(15) 0.0035(12) 0.0023(10) -0.0094(11) C26B 0.0183(11) 0.0309(13) 0.0230(12) 0.0031(10) 0.0006(9) -0.0002(10) C11 0.0185(11) 0.0170(10) 0.0168(11) 0.0019(8) 0.0013(8) -0.0002(9) C22 0.0208(11) 0.0164(10) 0.0174(11) -0.0068(8) 0.0038(9) -0.0021(9) C4 0.0187(11) 0.0139(10) 0.0179(11) -0.0063(8) 0.0009(9) -0.0037(9) C22B 0.0242(12) 0.0197(11) 0.0233(12) 0.0029(9) 0.0021(10) -0.0029(10) C23 0.0271(12) 0.0203(11) 0.0242(12) -0.0018(9) 0.0104(10) -0.0077(10) C6 0.0279(12) 0.0248(12) 0.0167(11) -0.0071(9) -0.0005(9) -0.0059(10) C2 0.0132(10) 0.0147(10) 0.0129(10) -0.0016(8) -0.0007(8) -0.0004(8) C3 0.0178(11) 0.0157(10) 0.0188(11) -0.0026(8) 0.0003(9) -0.0040(9) C25 0.0129(11) 0.0338(13) 0.0287(13) -0.0035(10) 0.0012(9) -0.0009(10) C15 0.0148(10) 0.0246(11) 0.0140(11) 0.0003(9) -0.0020(8) 0.0028(9) C5 0.0238(12) 0.0192(11) 0.0297(13) -0.0101(9) 0.0034(10) -0.0006(10) C101 0.068(4) 0.073(3) 0.081(4) 0.030(3) 0.000 0.000 C100 0.088(3) 0.087(3) 0.057(2) 0.013(2) 0.0100(19) 0.005(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.364(2) . ? N1 C21 1.444(2) . ? N1 C4 1.491(2) . ? P2 P1 2.1982(8) . ? P2 P2 2.2337(10) 4_665 ? P2 P2 2.2570(11) 3_655 ? P1 C1 1.737(2) . ? C21 C22 1.404(3) . ? C21 C26 1.408(3) . ? C26A C26B 1.531(3) . ? C26A H26A 0.9800 . ? C26A H26B 0.9800 . ? C26A H26C 0.9800 . ? C1 C2 1.531(3) . ? C22A C22B 1.529(3) . ? C22A H22A 0.9800 . ? C22A H22B 0.9800 . ? C22A H22C 0.9800 . ? C14 C13 1.519(3) . ? C14 C15 1.524(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C26 C25 1.392(3) . ? C26 C26B 1.519(3) . ? C22C C22B 1.530(3) . ? C22C H22D 0.9800 . ? C22C H22E 0.9800 . ? C22C H22F 0.9800 . ? C12 C11 1.520(3) . ? C12 C13 1.524(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C26C C26B 1.535(3) . ? C26C H26D 0.9800 . ? C26C H26E 0.9800 . ? C26C H26F 0.9800 . ? C24 C23 1.374(3) . ? C24 C25 1.375(3) . ? C24 H24A 0.9500 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C26B H26G 1.0000 . ? C11 C2 1.537(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C22 C23 1.399(3) . ? C22 C22B 1.515(3) . ? C4 C5 1.517(3) . ? C4 C6 1.530(3) . ? C4 C3 1.530(3) . ? C22B H22G 1.0000 . ? C23 H23A 0.9500 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C2 C15 1.545(3) . ? C2 C3 1.546(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C25 H25A 0.9500 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C101 C100 1.365(4) 2 ? C101 C100 1.365(4) . ? C101 H10A 0.9500 . ? C100 C100 1.392(8) 4_655 ? C100 H10B 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C21 121.77(16) . . ? C1 N1 C4 115.17(16) . . ? C21 N1 C4 123.03(15) . . ? P1 P2 P2 93.31(3) . 4_665 ? P1 P2 P2 102.54(4) . 3_655 ? P2 P2 P2 84.855(15) 4_665 3_655 ? C1 P1 P2 106.16(7) . . ? C22 C21 C26 121.51(19) . . ? C22 C21 N1 119.82(18) . . ? C26 C21 N1 118.63(17) . . ? C26B C26A H26A 109.5 . . ? C26B C26A H26B 109.5 . . ? H26A C26A H26B 109.5 . . ? C26B C26A H26C 109.5 . . ? H26A C26A H26C 109.5 . . ? H26B C26A H26C 109.5 . . ? N1 C1 C2 108.33(16) . . ? N1 C1 P1 118.21(14) . . ? C2 C1 P1 133.43(15) . . ? C22B C22A H22A 109.5 . . ? C22B C22A H22B 109.5 . . ? H22A C22A H22B 109.5 . . ? C22B C22A H22C 109.5 . . ? H22A C22A H22C 109.5 . . ? H22B C22A H22C 109.5 . . ? C13 C14 C15 111.12(18) . . ? C13 C14 H14A 109.4 . . ? C15 C14 H14A 109.4 . . ? C13 C14 H14B 109.4 . . ? C15 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? C25 C26 C21 118.0(2) . . ? C25 C26 C26B 118.4(2) . . ? C21 C26 C26B 123.44(18) . . ? C22B C22C H22D 109.5 . . ? C22B C22C H22E 109.5 . . ? H22D C22C H22E 109.5 . . ? C22B C22C H22F 109.5 . . ? H22D C22C H22F 109.5 . . ? H22E C22C H22F 109.5 . . ? C11 C12 C13 110.99(18) . . ? C11 C12 H12A 109.4 . . ? C13 C12 H12A 109.4 . . ? C11 C12 H12B 109.4 . . ? C13 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C26B C26C H26D 109.5 . . ? C26B C26C H26E 109.5 . . ? H26D C26C H26E 109.5 . . ? C26B C26C H26F 109.5 . . ? H26D C26C H26F 109.5 . . ? H26E C26C H26F 109.5 . . ? C23 C24 C25 120.0(2) . . ? C23 C24 H24A 120.0 . . ? C25 C24 H24A 120.0 . . ? C14 C13 C12 111.29(19) . . ? C14 C13 H13A 109.4 . . ? C12 C13 H13A 109.4 . . ? C14 C13 H13B 109.4 . . ? C12 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? C26 C26B C26A 110.20(19) . . ? C26 C26B C26C 112.33(18) . . ? C26A C26B C26C 109.54(19) . . ? C26 C26B H26G 108.2 . . ? C26A C26B H26G 108.2 . . ? C26C C26B H26G 108.2 . . ? C12 C11 C2 111.48(17) . . ? C12 C11 H11A 109.3 . . ? C2 C11 H11A 109.3 . . ? C12 C11 H11B 109.3 . . ? C2 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C23 C22 C21 117.4(2) . . ? C23 C22 C22B 118.70(19) . . ? C21 C22 C22B 123.81(19) . . ? N1 C4 C5 111.38(17) . . ? N1 C4 C6 112.00(16) . . ? C5 C4 C6 108.29(17) . . ? N1 C4 C3 100.42(15) . . ? C5 C4 C3 112.33(17) . . ? C6 C4 C3 112.34(17) . . ? C22 C22B C22A 110.45(19) . . ? C22 C22B C22C 112.37(19) . . ? C22A C22B C22C 110.42(19) . . ? C22 C22B H22G 107.8 . . ? C22A C22B H22G 107.8 . . ? C22C C22B H22G 107.8 . . ? C24 C23 C22 121.7(2) . . ? C24 C23 H23A 119.1 . . ? C22 C23 H23A 119.1 . . ? 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 . . ? C1 C2 C11 112.11(16) . . ? C1 C2 C15 111.00(16) . . ? C11 C2 C15 108.86(16) . . ? C1 C2 C3 102.47(16) . . ? C11 C2 C3 110.15(16) . . ? C15 C2 C3 112.19(16) . . ? C4 C3 C2 107.70(16) . . ? C4 C3 H3A 110.2 . . ? C2 C3 H3A 110.2 . . ? C4 C3 H3B 110.2 . . ? C2 C3 H3B 110.2 . . ? H3A C3 H3B 108.5 . . ? C24 C25 C26 121.3(2) . . ? C24 C25 H25A 119.4 . . ? C26 C25 H25A 119.4 . . ? C14 C15 C2 112.43(17) . . ? C14 C15 H15A 109.1 . . ? C2 C15 H15A 109.1 . . ? C14 C15 H15B 109.1 . . ? C2 C15 H15B 109.1 . . ? H15A C15 H15B 107.8 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C100 C101 C100 120.3(5) 2 . ? C100 C101 H10A 119.8 2 . ? C100 C101 H10A 119.8 . . ? C101 C100 C100 119.8(3) . 4_655 ? C101 C100 H10B 120.1 . . ? C100 C100 H10B 120.1 4_655 . ? 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 P2 P2 P1 C1 -148.22(7) 4_665 . . . ? P2 P2 P1 C1 126.32(7) 3_655 . . . ? C1 N1 C21 C22 -87.9(2) . . . . ? C4 N1 C21 C22 90.1(2) . . . . ? C1 N1 C21 C26 89.8(2) . . . . ? C4 N1 C21 C26 -92.2(2) . . . . ? C21 N1 C1 C2 -178.12(16) . . . . ? C4 N1 C1 C2 3.8(2) . . . . ? C21 N1 C1 P1 0.1(2) . . . . ? C4 N1 C1 P1 -178.01(14) . . . . ? P2 P1 C1 N1 169.04(13) . . . . ? P2 P1 C1 C2 -13.3(2) . . . . ? C22 C21 C26 C25 -3.4(3) . . . . ? N1 C21 C26 C25 178.94(18) . . . . ? C22 C21 C26 C26B 172.42(19) . . . . ? N1 C21 C26 C26B -5.2(3) . . . . ? C15 C14 C13 C12 -54.7(3) . . . . ? C11 C12 C13 C14 56.2(3) . . . . ? C25 C26 C26B C26A 62.7(3) . . . . ? C21 C26 C26B C26A -113.1(2) . . . . ? C25 C26 C26B C26C -59.8(3) . . . . ? C21 C26 C26B C26C 124.4(2) . . . . ? C13 C12 C11 C2 -57.9(2) . . . . ? C26 C21 C22 C23 3.5(3) . . . . ? N1 C21 C22 C23 -178.84(17) . . . . ? C26 C21 C22 C22B -172.80(19) . . . . ? N1 C21 C22 C22B 4.8(3) . . . . ? C1 N1 C4 C5 -136.62(18) . . . . ? C21 N1 C4 C5 45.3(3) . . . . ? C1 N1 C4 C6 101.9(2) . . . . ? C21 N1 C4 C6 -76.1(2) . . . . ? C1 N1 C4 C3 -17.5(2) . . . . ? C21 N1 C4 C3 164.48(17) . . . . ? C23 C22 C22B C22A -65.2(2) . . . . ? C21 C22 C22B C22A 111.1(2) . . . . ? C23 C22 C22B C22C 58.6(3) . . . . ? C21 C22 C22B C22C -125.1(2) . . . . ? C25 C24 C23 C22 -1.3(3) . . . . ? C21 C22 C23 C24 -1.2(3) . . . . ? C22B C22 C23 C24 175.4(2) . . . . ? N1 C1 C2 C11 129.69(17) . . . . ? P1 C1 C2 C11 -48.1(3) . . . . ? N1 C1 C2 C15 -108.33(18) . . . . ? P1 C1 C2 C15 73.9(2) . . . . ? N1 C1 C2 C3 11.6(2) . . . . ? P1 C1 C2 C3 -166.17(17) . . . . ? C12 C11 C2 C1 179.68(17) . . . . ? C12 C11 C2 C15 56.5(2) . . . . ? C12 C11 C2 C3 -66.9(2) . . . . ? N1 C4 C3 C2 23.8(2) . . . . ? C5 C4 C3 C2 142.26(17) . . . . ? C6 C4 C3 C2 -95.35(19) . . . . ? C1 C2 C3 C4 -22.4(2) . . . . ? C11 C2 C3 C4 -141.84(17) . . . . ? C15 C2 C3 C4 96.73(19) . . . . ? C23 C24 C25 C26 1.5(3) . . . . ? C21 C26 C25 C24 0.9(3) . . . . ? C26B C26 C25 C24 -175.2(2) . . . . ? C13 C14 C15 C2 55.1(2) . . . . ? C1 C2 C15 C14 -179.22(17) . . . . ? C11 C2 C15 C14 -55.4(2) . . . . ? C3 C2 C15 C14 66.8(2) . . . . ? C100 C101 C100 C100 -0.1(4) 2 . . 4_655 ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.44 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.287 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.056 data_gbcm6 _database_code_depnum_ccdc_archive 'CCDC 930073' #TrackingRef '18672_web_deposit_cif_file_2_CalebMartin_1363713550.4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H26 N2 O2 P4, 1/3(C H Cl3)' _chemical_formula_sum 'C27.33 H26.33 Cl N2 O2 P4' _chemical_formula_weight 534.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M R-3 _symmetry_space_group_name_Hall '-R 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 34.4341(10) _cell_length_b 34.4341(10) _cell_length_c 11.4555(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 11763.1(6) _cell_formula_units_Z 18 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 38590 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 26.41 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5004 _exptl_absorpt_coefficient_mu 0.421 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9452 _exptl_absorpt_correction_T_max 0.9600 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean '512 x 512' _diffrn_reflns_number 38581 _diffrn_reflns_av_R_equivalents 0.1185 _diffrn_reflns_av_sigmaI/netI 0.0823 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 43 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 26.37 _reflns_number_total 5356 _reflns_number_gt 3775 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'BRUKER SHELXTL' _computing_publication_material 'BRUKER SHELXTL' _refine_special_details ; SQUEEZE found 3 voids containing 2 disordered molecules of chloroform in each. Their formula was added to the formula for the unit cell and the electron density removed. 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^)+(0.0701P)^2^+22.8677P] 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 5356 _refine_ls_number_parameters 322 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1090 _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.1495 _refine_ls_wR_factor_gt 0.1355 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 -0.004 355 109 '2 Molecules of Chloroform' 2 0.333 0.667 0.311 354 109 '2 Molecules of Chloroform' 3 0.667 0.333 -0.023 354 109 '2 Molecules of Chloroform' _platon_squeeze_details ; SQUEEZE found 3 voids containing 2 disordered molecules of chloroform in each. Their formula was added to the formula for the unit cell and the electron density removed. ; 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 -0.03594(3) -0.18746(3) -0.05890(8) 0.0182(2) Uani 1 1 d . . . P2 P 0.04649(3) -0.11175(3) -0.09068(8) 0.0181(2) Uani 1 1 d . . . P3 P -0.01772(3) -0.11595(3) -0.04166(9) 0.0235(3) Uani 1 1 d . . . P4 P 0.01168(3) -0.14371(3) 0.07672(8) 0.0225(2) Uani 1 1 d . . . O1 O 0.02187(8) -0.13616(8) -0.4608(2) 0.0235(6) Uani 1 1 d . . . O2 O 0.09382(8) -0.20695(8) -0.2038(2) 0.0235(6) Uani 1 1 d . . . N1 N 0.00240(9) -0.16995(9) -0.2838(2) 0.0143(6) Uani 1 1 d . . . N2 N 0.03691(9) -0.19628(9) -0.1442(2) 0.0144(6) Uani 1 1 d . . . C1 C 0.01403(11) -0.16985(11) -0.1616(3) 0.0131(7) Uani 1 1 d . . . C2 C 0.03323(11) -0.14123(11) -0.3636(3) 0.0169(8) Uani 1 1 d . . . C3 C 0.07624(11) -0.18374(11) -0.2056(3) 0.0176(8) Uani 1 1 d . . . C101 C 0.08076(11) -0.11723(11) -0.3260(3) 0.0179(8) Uani 1 1 d . . . C102 C 0.10756(12) -0.07348(12) -0.3671(3) 0.0216(8) Uani 1 1 d . . . H10A H 0.0946 -0.0600 -0.4135 0.026 Uiso 1 1 calc R . . C103 C 0.15267(12) -0.04963(12) -0.3408(3) 0.0250(9) Uani 1 1 d . . . H10B H 0.1705 -0.0194 -0.3655 0.030 Uiso 1 1 calc R . . C104 C 0.17177(13) -0.07009(13) -0.2781(3) 0.0279(9) Uani 1 1 d . . . H10D H 0.2029 -0.0538 -0.2607 0.033 Uiso 1 1 calc R . . C105 C 0.14628(11) -0.11392(13) -0.2404(3) 0.0225(8) Uani 1 1 d . . . H10C H 0.1602 -0.1279 -0.2001 0.027 Uiso 1 1 calc R . . C106 C 0.09985(11) -0.13795(11) -0.2612(3) 0.0162(7) Uani 1 1 d . . . C201 C -0.04213(11) -0.20135(11) -0.3291(3) 0.0150(7) Uani 1 1 d . . . C202 C -0.07560(11) -0.18978(11) -0.3299(3) 0.0168(8) Uani 1 1 d . . . C203 C -0.11834(12) -0.22195(12) -0.3665(3) 0.0202(8) Uani 1 1 d . . . H20E H -0.1421 -0.2156 -0.3607 0.024 Uiso 1 1 calc R . . C204 C -0.12712(12) -0.26304(12) -0.4111(3) 0.0198(8) Uani 1 1 d . . . C205 C -0.09162(12) -0.27114(12) -0.4209(3) 0.0197(8) Uani 1 1 d . . . H20A H -0.0968 -0.2984 -0.4557 0.024 Uiso 1 1 calc R . . C206 C -0.04905(12) -0.24107(11) -0.3818(3) 0.0165(8) Uani 1 1 d . . . C207 C -0.06606(12) -0.14275(12) -0.3074(3) 0.0231(8) Uani 1 1 d . . . H20F H -0.0800 -0.1339 -0.3687 0.035 Uiso 1 1 calc R . . H20G H -0.0336 -0.1222 -0.3077 0.035 Uiso 1 1 calc R . . H20H H -0.0784 -0.1415 -0.2313 0.035 Uiso 1 1 calc R . . C208 C -0.01037(12) -0.24883(12) -0.4060(3) 0.0215(8) Uani 1 1 d . . . H20B H -0.0216 -0.2779 -0.4443 0.032 Uiso 1 1 calc R . . H20C H 0.0042 -0.2485 -0.3323 0.032 Uiso 1 1 calc R . . H20D H 0.0113 -0.2250 -0.4571 0.032 Uiso 1 1 calc R . . C209 C -0.17316(11) -0.29666(12) -0.4551(3) 0.0203(8) Uani 1 1 d . . . H20I H -0.1713 -0.3030 -0.5377 0.030 Uiso 1 1 calc R . . H20J H -0.1933 -0.2844 -0.4462 0.030 Uiso 1 1 calc R . . H20K H -0.1848 -0.3245 -0.4100 0.030 Uiso 1 1 calc R . . C301 C 0.02870(11) -0.22329(11) -0.0399(3) 0.0157(7) Uani 1 1 d . . . C302 C -0.01143(12) -0.26416(11) -0.0267(3) 0.0179(8) Uani 1 1 d . . . C303 C -0.01967(12) -0.28661(12) 0.0804(3) 0.0203(8) Uani 1 1 d . . . H30A H -0.0470 -0.3140 0.0905 0.024 Uiso 1 1 calc R . . C304 C 0.01054(13) -0.27032(12) 0.1715(3) 0.0216(8) Uani 1 1 d . . . C305 C 0.05042(12) -0.23059(13) 0.1552(3) 0.0216(8) Uani 1 1 d . . . H30E H 0.0715 -0.2193 0.2173 0.026 Uiso 1 1 calc R . . C306 C 0.06080(12) -0.20656(12) 0.0511(3) 0.0186(8) Uani 1 1 d . . . C307 C -0.04526(12) -0.28657(12) -0.1224(3) 0.0241(9) Uani 1 1 d . . . H30F H -0.0738 -0.3093 -0.0887 0.036 Uiso 1 1 calc R . . H30G H -0.0344 -0.3009 -0.1772 0.036 Uiso 1 1 calc R . . H30H H -0.0496 -0.2641 -0.1639 0.036 Uiso 1 1 calc R . . C308 C 0.00056(14) -0.29509(14) 0.2849(3) 0.0300(9) Uani 1 1 d . . . H30I H 0.0151 -0.2737 0.3487 0.045 Uiso 1 1 calc R . . H30J H 0.0120 -0.3161 0.2824 0.045 Uiso 1 1 calc R . . H30K H -0.0319 -0.3118 0.2977 0.045 Uiso 1 1 calc R . . C309 C 0.10538(12) -0.16445(12) 0.0412(3) 0.0240(9) Uani 1 1 d . . . H30B H 0.1166 -0.1526 0.1193 0.036 Uiso 1 1 calc R . . H30C H 0.1020 -0.1422 -0.0042 0.036 Uiso 1 1 calc R . . H30D H 0.1267 -0.1711 0.0019 0.036 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 0.0127(5) 0.0193(5) 0.0183(5) 0.0007(4) 0.0024(4) 0.0047(4) P2 0.0151(5) 0.0158(5) 0.0192(5) -0.0024(4) 0.0018(4) 0.0046(4) P3 0.0204(5) 0.0228(5) 0.0275(6) -0.0013(4) 0.0039(4) 0.0109(4) P4 0.0203(5) 0.0250(5) 0.0173(5) -0.0037(4) 0.0007(4) 0.0077(4) O1 0.0204(14) 0.0281(15) 0.0175(13) 0.0068(11) 0.0007(11) 0.0088(12) O2 0.0219(14) 0.0228(14) 0.0294(15) -0.0031(11) -0.0019(11) 0.0140(12) N1 0.0109(14) 0.0131(15) 0.0164(15) 0.0007(12) -0.0012(12) 0.0041(12) N2 0.0104(14) 0.0148(15) 0.0162(15) 0.0012(12) -0.0003(12) 0.0050(12) C1 0.0124(17) 0.0136(17) 0.0104(17) -0.0018(14) -0.0002(14) 0.0042(14) C2 0.0168(18) 0.0133(18) 0.0176(19) 0.0000(14) 0.0011(15) 0.0053(15) C3 0.0138(18) 0.0195(19) 0.0166(18) -0.0063(15) -0.0063(15) 0.0061(16) C101 0.0179(19) 0.0170(18) 0.0147(18) -0.0028(15) 0.0041(14) 0.0058(15) C102 0.022(2) 0.021(2) 0.0182(19) -0.0012(16) 0.0038(16) 0.0081(17) C103 0.024(2) 0.019(2) 0.0181(19) -0.0023(16) 0.0048(16) 0.0003(17) C104 0.017(2) 0.028(2) 0.022(2) -0.0030(17) 0.0019(16) -0.0010(17) C105 0.0131(18) 0.032(2) 0.0187(19) -0.0052(17) -0.0014(15) 0.0088(17) C106 0.0139(17) 0.0169(18) 0.0145(17) -0.0032(14) 0.0023(14) 0.0053(15) C201 0.0116(17) 0.0143(17) 0.0143(18) 0.0014(14) 0.0000(14) 0.0029(15) C202 0.0148(18) 0.0171(18) 0.0170(18) 0.0011(15) -0.0002(14) 0.0068(15) C203 0.0167(18) 0.026(2) 0.0187(19) 0.0074(16) 0.0033(15) 0.0117(17) C204 0.0178(19) 0.0209(19) 0.0132(18) 0.0043(15) -0.0013(15) 0.0041(16) C205 0.024(2) 0.0142(18) 0.0148(18) 0.0000(15) -0.0005(15) 0.0054(16) C206 0.0220(19) 0.0162(18) 0.0122(17) 0.0027(14) 0.0007(15) 0.0103(16) C207 0.022(2) 0.024(2) 0.026(2) -0.0038(16) -0.0018(16) 0.0131(17) C208 0.024(2) 0.0170(19) 0.023(2) -0.0039(15) 0.0013(16) 0.0099(16) C209 0.0147(18) 0.0171(19) 0.0194(19) 0.0031(15) -0.0037(15) 0.0007(15) C301 0.0157(18) 0.0138(17) 0.0174(18) 0.0009(14) 0.0007(14) 0.0072(15) C302 0.0184(18) 0.0161(18) 0.0199(19) -0.0022(15) -0.0015(15) 0.0090(15) C303 0.0192(19) 0.0173(19) 0.025(2) 0.0026(16) 0.0055(16) 0.0094(16) C304 0.029(2) 0.027(2) 0.0203(19) 0.0027(16) 0.0030(17) 0.0229(18) C305 0.024(2) 0.030(2) 0.0182(19) -0.0012(16) -0.0037(16) 0.0183(18) C306 0.0181(19) 0.0192(19) 0.023(2) -0.0031(15) -0.0024(15) 0.0126(16) C307 0.0191(19) 0.020(2) 0.024(2) 0.0003(16) -0.0023(16) 0.0020(16) C308 0.034(2) 0.037(2) 0.026(2) 0.0096(19) 0.0055(18) 0.023(2) C309 0.021(2) 0.026(2) 0.022(2) -0.0047(17) -0.0090(16) 0.0099(17) _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 C1 1.916(3) . ? P1 P4 2.2140(13) . ? P1 P3 2.2252(14) . ? P2 C1 1.917(3) . ? P2 P3 2.2147(13) . ? P2 P4 2.2374(13) . ? P3 P4 2.1784(15) . ? O1 C2 1.221(4) . ? O2 C3 1.220(4) . ? N1 C2 1.375(4) . ? N1 C1 1.456(4) . ? N1 C201 1.460(4) . ? N2 C3 1.389(4) . ? N2 C301 1.452(4) . ? N2 C1 1.485(4) . ? C2 C101 1.481(5) . ? C3 C106 1.507(5) . ? C101 C102 1.397(5) . ? C101 C106 1.400(5) . ? C102 C103 1.379(5) . ? C102 H10A 0.9500 . ? C103 C104 1.381(6) . ? C103 H10B 0.9500 . ? C104 C105 1.383(5) . ? C104 H10D 0.9500 . ? C105 C106 1.405(5) . ? C105 H10C 0.9500 . ? C201 C202 1.395(5) . ? C201 C206 1.402(5) . ? C202 C203 1.392(5) . ? C202 C207 1.505(5) . ? C203 C204 1.388(5) . ? C203 H20E 0.9500 . ? C204 C205 1.388(5) . ? C204 C209 1.507(5) . ? C205 C206 1.380(5) . ? C205 H20A 0.9500 . ? C206 C208 1.509(5) . ? C207 H20F 0.9800 . ? C207 H20G 0.9800 . ? C207 H20H 0.9800 . ? C208 H20B 0.9800 . ? C208 H20C 0.9800 . ? C208 H20D 0.9800 . ? C209 H20I 0.9800 . ? C209 H20J 0.9800 . ? C209 H20K 0.9800 . ? C301 C302 1.403(5) . ? C301 C306 1.415(5) . ? C302 C303 1.400(5) . ? C302 C307 1.502(5) . ? C303 C304 1.380(5) . ? C303 H30A 0.9500 . ? C304 C305 1.383(5) . ? C304 C308 1.496(5) . ? C305 C306 1.392(5) . ? C305 H30E 0.9500 . ? C306 C309 1.499(5) . ? C307 H30F 0.9800 . ? C307 H30G 0.9800 . ? C307 H30H 0.9800 . ? C308 H30I 0.9800 . ? C308 H30J 0.9800 . ? C308 H30K 0.9800 . ? C309 H30B 0.9800 . ? C309 H30C 0.9800 . ? C309 H30D 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 C1 P1 P4 88.46(10) . . ? C1 P1 P3 89.57(11) . . ? P4 P1 P3 58.78(4) . . ? C1 P2 P3 89.85(10) . . ? C1 P2 P4 87.74(10) . . ? P3 P2 P4 58.59(4) . . ? P4 P3 P2 61.23(4) . . ? P4 P3 P1 60.35(4) . . ? P2 P3 P1 76.68(4) . . ? P3 P4 P1 60.87(4) . . ? P3 P4 P2 60.19(4) . . ? P1 P4 P2 76.45(4) . . ? C2 N1 C1 121.7(3) . . ? C2 N1 C201 116.4(3) . . ? C1 N1 C201 121.9(3) . . ? C3 N2 C301 117.6(3) . . ? C3 N2 C1 118.3(3) . . ? C301 N2 C1 120.7(3) . . ? N1 C1 N2 111.0(3) . . ? N1 C1 P1 112.8(2) . . ? N2 C1 P1 113.0(2) . . ? N1 C1 P2 115.2(2) . . ? N2 C1 P2 111.8(2) . . ? P1 C1 P2 91.87(14) . . ? O1 C2 N1 121.4(3) . . ? O1 C2 C101 121.9(3) . . ? N1 C2 C101 116.7(3) . . ? O2 C3 N2 120.9(3) . . ? O2 C3 C106 120.5(3) . . ? N2 C3 C106 118.1(3) . . ? C102 C101 C106 120.2(3) . . ? C102 C101 C2 117.0(3) . . ? C106 C101 C2 122.6(3) . . ? C103 C102 C101 120.6(4) . . ? C103 C102 H10A 119.7 . . ? C101 C102 H10A 119.7 . . ? C102 C103 C104 119.4(4) . . ? C102 C103 H10B 120.3 . . ? C104 C103 H10B 120.3 . . ? C103 C104 C105 121.0(4) . . ? C103 C104 H10D 119.5 . . ? C105 C104 H10D 119.5 . . ? C104 C105 C106 120.3(4) . . ? C104 C105 H10C 119.9 . . ? C106 C105 H10C 119.9 . . ? C101 C106 C105 118.4(3) . . ? C101 C106 C3 127.7(3) . . ? C105 C106 C3 113.8(3) . . ? C202 C201 C206 120.9(3) . . ? C202 C201 N1 120.2(3) . . ? C206 C201 N1 118.6(3) . . ? C203 C202 C201 118.0(3) . . ? C203 C202 C207 118.9(3) . . ? C201 C202 C207 122.6(3) . . ? C204 C203 C202 121.8(3) . . ? C204 C203 H20E 119.1 . . ? C202 C203 H20E 119.1 . . ? C205 C204 C203 118.0(3) . . ? C205 C204 C209 120.8(3) . . ? C203 C204 C209 121.0(3) . . ? C206 C205 C204 122.4(3) . . ? C206 C205 H20A 118.8 . . ? C204 C205 H20A 118.8 . . ? C205 C206 C201 118.1(3) . . ? C205 C206 C208 120.5(3) . . ? C201 C206 C208 121.1(3) . . ? C202 C207 H20F 109.5 . . ? C202 C207 H20G 109.5 . . ? H20F C207 H20G 109.5 . . ? C202 C207 H20H 109.5 . . ? H20F C207 H20H 109.5 . . ? H20G C207 H20H 109.5 . . ? C206 C208 H20B 109.5 . . ? C206 C208 H20C 109.5 . . ? H20B C208 H20C 109.5 . . ? C206 C208 H20D 109.5 . . ? H20B C208 H20D 109.5 . . ? H20C C208 H20D 109.5 . . ? C204 C209 H20I 109.5 . . ? C204 C209 H20J 109.5 . . ? H20I C209 H20J 109.5 . . ? C204 C209 H20K 109.5 . . ? H20I C209 H20K 109.5 . . ? H20J C209 H20K 109.5 . . ? C302 C301 C306 120.4(3) . . ? C302 C301 N2 120.7(3) . . ? C306 C301 N2 118.9(3) . . ? C303 C302 C301 118.3(3) . . ? C303 C302 C307 117.7(3) . . ? C301 C302 C307 123.9(3) . . ? C304 C303 C302 122.3(3) . . ? C304 C303 H30A 118.8 . . ? C302 C303 H30A 118.8 . . ? C303 C304 C305 118.2(3) . . ? C303 C304 C308 120.9(3) . . ? C305 C304 C308 120.9(3) . . ? C304 C305 C306 122.5(3) . . ? C304 C305 H30E 118.8 . . ? C306 C305 H30E 118.8 . . ? C305 C306 C301 118.2(3) . . ? C305 C306 C309 118.3(3) . . ? C301 C306 C309 123.5(3) . . ? C302 C307 H30F 109.5 . . ? C302 C307 H30G 109.5 . . ? H30F C307 H30G 109.5 . . ? C302 C307 H30H 109.5 . . ? H30F C307 H30H 109.5 . . ? H30G C307 H30H 109.5 . . ? C304 C308 H30I 109.5 . . ? C304 C308 H30J 109.5 . . ? H30I C308 H30J 109.5 . . ? C304 C308 H30K 109.5 . . ? H30I C308 H30K 109.5 . . ? H30J C308 H30K 109.5 . . ? C306 C309 H30B 109.5 . . ? C306 C309 H30C 109.5 . . ? H30B C309 H30C 109.5 . . ? C306 C309 H30D 109.5 . . ? H30B C309 H30D 109.5 . . ? H30C C309 H30D 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 C1 P2 P3 P4 87.45(11) . . . . ? C1 P2 P3 P1 24.19(10) . . . . ? P4 P2 P3 P1 -63.26(4) . . . . ? C1 P1 P3 P4 -88.46(11) . . . . ? C1 P1 P3 P2 -24.21(10) . . . . ? P4 P1 P3 P2 64.25(4) . . . . ? P2 P3 P4 P1 -90.58(5) . . . . ? P1 P3 P4 P2 90.58(5) . . . . ? C1 P1 P4 P3 90.43(11) . . . . ? C1 P1 P4 P2 27.25(11) . . . . ? P3 P1 P4 P2 -63.18(4) . . . . ? C1 P2 P4 P3 -91.20(11) . . . . ? C1 P2 P4 P1 -27.24(10) . . . . ? P3 P2 P4 P1 63.96(5) . . . . ? C2 N1 C1 N2 -81.8(4) . . . . ? C201 N1 C1 N2 96.3(3) . . . . ? C2 N1 C1 P1 150.2(3) . . . . ? C201 N1 C1 P1 -31.7(4) . . . . ? C2 N1 C1 P2 46.5(4) . . . . ? C201 N1 C1 P2 -135.4(3) . . . . ? C3 N2 C1 N1 58.3(4) . . . . ? C301 N2 C1 N1 -143.1(3) . . . . ? C3 N2 C1 P1 -173.8(2) . . . . ? C301 N2 C1 P1 -15.2(4) . . . . ? C3 N2 C1 P2 -71.8(3) . . . . ? C301 N2 C1 P2 86.8(3) . . . . ? P4 P1 C1 N1 -149.8(2) . . . . ? P3 P1 C1 N1 -91.0(2) . . . . ? P4 P1 C1 N2 83.4(2) . . . . ? P3 P1 C1 N2 142.1(2) . . . . ? P4 P1 C1 P2 -31.32(11) . . . . ? P3 P1 C1 P2 27.46(11) . . . . ? P3 P2 C1 N1 88.7(2) . . . . ? P4 P2 C1 N1 147.3(2) . . . . ? P3 P2 C1 N2 -143.3(2) . . . . ? P4 P2 C1 N2 -84.8(2) . . . . ? P3 P2 C1 P1 -27.60(11) . . . . ? P4 P2 C1 P1 30.97(11) . . . . ? C1 N1 C2 O1 -167.9(3) . . . . ? C201 N1 C2 O1 13.8(5) . . . . ? C1 N1 C2 C101 12.7(4) . . . . ? C201 N1 C2 C101 -165.6(3) . . . . ? C301 N2 C3 O2 28.3(5) . . . . ? C1 N2 C3 O2 -172.4(3) . . . . ? C301 N2 C3 C106 -143.7(3) . . . . ? C1 N2 C3 C106 15.6(4) . . . . ? O1 C2 C101 C102 35.6(5) . . . . ? N1 C2 C101 C102 -144.9(3) . . . . ? O1 C2 C101 C106 -138.6(4) . . . . ? N1 C2 C101 C106 40.8(5) . . . . ? C106 C101 C102 C103 -2.4(5) . . . . ? C2 C101 C102 C103 -176.8(3) . . . . ? C101 C102 C103 C104 3.2(5) . . . . ? C102 C103 C104 C105 -0.7(6) . . . . ? C103 C104 C105 C106 -2.6(6) . . . . ? C102 C101 C106 C105 -0.8(5) . . . . ? C2 C101 C106 C105 173.3(3) . . . . ? C102 C101 C106 C3 177.1(3) . . . . ? C2 C101 C106 C3 -8.9(5) . . . . ? C104 C105 C106 C101 3.3(5) . . . . ? C104 C105 C106 C3 -174.9(3) . . . . ? O2 C3 C106 C101 143.1(4) . . . . ? N2 C3 C106 C101 -44.8(5) . . . . ? O2 C3 C106 C105 -38.9(5) . . . . ? N2 C3 C106 C105 133.1(3) . . . . ? C2 N1 C201 C202 -91.3(4) . . . . ? C1 N1 C201 C202 90.4(4) . . . . ? C2 N1 C201 C206 82.4(4) . . . . ? C1 N1 C201 C206 -95.8(4) . . . . ? C206 C201 C202 C203 10.7(5) . . . . ? N1 C201 C202 C203 -175.7(3) . . . . ? C206 C201 C202 C207 -161.6(3) . . . . ? N1 C201 C202 C207 12.0(5) . . . . ? C201 C202 C203 C204 -5.8(5) . . . . ? C207 C202 C203 C204 166.8(3) . . . . ? C202 C203 C204 C205 -1.3(5) . . . . ? C202 C203 C204 C209 -177.3(3) . . . . ? C203 C204 C205 C206 3.8(5) . . . . ? C209 C204 C205 C206 179.8(3) . . . . ? C204 C205 C206 C201 0.9(5) . . . . ? C204 C205 C206 C208 -173.2(3) . . . . ? C202 C201 C206 C205 -8.3(5) . . . . ? N1 C201 C206 C205 178.0(3) . . . . ? C202 C201 C206 C208 165.8(3) . . . . ? N1 C201 C206 C208 -7.9(5) . . . . ? C3 N2 C301 C302 -126.0(3) . . . . ? C1 N2 C301 C302 75.2(4) . . . . ? C3 N2 C301 C306 57.4(4) . . . . ? C1 N2 C301 C306 -101.4(4) . . . . ? C306 C301 C302 C303 3.0(5) . . . . ? N2 C301 C302 C303 -173.5(3) . . . . ? C306 C301 C302 C307 -173.9(3) . . . . ? N2 C301 C302 C307 9.6(5) . . . . ? C301 C302 C303 C304 -1.2(5) . . . . ? C307 C302 C303 C304 175.9(3) . . . . ? C302 C303 C304 C305 -0.6(5) . . . . ? C302 C303 C304 C308 179.8(3) . . . . ? C303 C304 C305 C306 0.6(5) . . . . ? C308 C304 C305 C306 -179.8(3) . . . . ? C304 C305 C306 C301 1.3(5) . . . . ? C304 C305 C306 C309 -178.6(3) . . . . ? C302 C301 C306 C305 -3.1(5) . . . . ? N2 C301 C306 C305 173.6(3) . . . . ? C302 C301 C306 C309 176.7(3) . . . . ? N2 C301 C306 C309 -6.6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.572 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.122