# 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_z _database_code_depnum_ccdc_archive 'CCDC 903374' #TrackingRef 'web_deposit_cif_file_0_JunJiang_1357202919.Z.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H38 Br N2 O8 P' _chemical_formula_weight 725.55 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.9476(6) _cell_length_b 14.5627(5) _cell_length_c 15.6857(5) _cell_angle_alpha 90.00 _cell_angle_beta 116.6200(10) _cell_angle_gamma 90.00 _cell_volume 3460.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 1.287 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8109 _exptl_absorpt_correction_T_max 0.9503 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 39890 _diffrn_reflns_av_R_equivalents 0.0746 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 25.01 _reflns_number_total 6095 _reflns_number_gt 3424 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0889P)^2^+8.8222P] 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 6095 _refine_ls_number_parameters 424 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1357 _refine_ls_R_factor_gt 0.0752 _refine_ls_wR_factor_ref 0.2318 _refine_ls_wR_factor_gt 0.1901 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.38391(7) 0.08370(6) 0.05038(8) 0.1114(4) Uani 1 1 d . . . P1 P 0.18219(10) -0.27690(11) -0.25620(10) 0.0516(4) Uani 1 1 d . . . O1 O 0.1270(3) -0.2039(3) -0.2309(3) 0.0641(12) Uani 1 1 d . . . O2 O 0.1042(2) -0.3390(3) -0.3280(3) 0.0570(11) Uani 1 1 d . . . O3 O 0.2423(3) -0.2422(3) -0.2913(3) 0.0597(11) Uani 1 1 d . . . O4 O 0.2634(3) -0.4187(3) 0.0011(3) 0.0721(13) Uani 1 1 d . . . O5 O 0.4044(3) -0.3775(3) 0.0752(3) 0.0592(11) Uani 1 1 d . . . O6 O 0.3858(4) -0.5174(3) -0.0760(4) 0.108(2) Uani 1 1 d . . . O7 O 0.3469(4) -0.4887(3) -0.2261(3) 0.0806(14) Uani 1 1 d . . . O8 O 0.7052(4) -0.2978(4) -0.2333(4) 0.0960(17) Uani 1 1 d . . . N1 N 0.2306(3) -0.3368(3) -0.1582(3) 0.0520(12) Uani 1 1 d . . . H1A H 0.2007 -0.3805 -0.1498 0.062 Uiso 1 1 calc R . . N2 N 0.4757(3) -0.3404(3) -0.0687(3) 0.0562(13) Uani 1 1 d . . . H2A H 0.4980 -0.3339 -0.0078 0.067 Uiso 1 1 calc R . . C1 C 0.0999(4) -0.3544(5) -0.4830(4) 0.0646(18) Uani 1 1 d . . . C2 C 0.1040(5) -0.4147(7) -0.5496(5) 0.085(3) Uani 1 1 d . . . H2B H 0.0991 -0.3911 -0.6069 0.102 Uiso 1 1 calc R . . C3 C 0.1147(5) -0.5053(7) -0.5347(6) 0.092(3) Uani 1 1 d . . . H3B H 0.1183 -0.5429 -0.5808 0.110 Uiso 1 1 calc R . . C4 C 0.1206(5) -0.5434(6) -0.4517(6) 0.087(2) Uani 1 1 d . . . H4A H 0.1258 -0.6067 -0.4434 0.105 Uiso 1 1 calc R . . C5 C 0.1187(4) -0.4883(5) -0.3805(5) 0.0646(17) Uani 1 1 d . . . C6 C 0.1106(4) -0.3955(5) -0.3972(4) 0.0580(16) Uani 1 1 d . . . C7 C 0.1193(5) -0.5291(5) -0.2924(5) 0.085(2) Uani 1 1 d . . . H7A H 0.1185 -0.4807 -0.2512 0.128 Uiso 1 1 calc R . . H7B H 0.1715 -0.5655 -0.2598 0.128 Uiso 1 1 calc R . . H7C H 0.0681 -0.5671 -0.3099 0.128 Uiso 1 1 calc R . . C8 C 0.0819(5) -0.2551(6) -0.5034(5) 0.089(2) Uani 1 1 d . . . H8A H 0.0788 -0.2413 -0.5646 0.134 Uiso 1 1 calc R . . H8B H 0.1284 -0.2199 -0.4552 0.134 Uiso 1 1 calc R . . H8C H 0.0268 -0.2398 -0.5034 0.134 Uiso 1 1 calc R . . C9 C 0.0911(8) -0.0598(7) -0.3164(6) 0.105(3) Uani 1 1 d . . . C10 C 0.0231(11) -0.0023(9) -0.3796(8) 0.153(5) Uani 1 1 d . . . H10A H 0.0356 0.0551 -0.3966 0.184 Uiso 1 1 calc R . . C11 C -0.0628(12) -0.0339(17) -0.4156(10) 0.187(11) Uani 1 1 d . . . H11A H -0.1057 0.0030 -0.4615 0.225 Uiso 1 1 calc R . . C12 C -0.0911(12) -0.1084(15) -0.3932(10) 0.167(8) Uani 1 1 d . . . H12A H -0.1510 -0.1208 -0.4161 0.200 Uiso 1 1 calc R . . C13 C -0.0234(6) -0.1718(9) -0.3300(6) 0.115(4) Uani 1 1 d . . . C14 C 0.0619(5) -0.1438(7) -0.2980(5) 0.080(2) Uani 1 1 d . . . C15 C 0.1844(8) -0.0332(7) -0.2730(9) 0.138(4) Uani 1 1 d . . . H15A H 0.2195 -0.0816 -0.2320 0.207 Uiso 1 1 calc R . . H15B H 0.1925 0.0219 -0.2364 0.207 Uiso 1 1 calc R . . H15C H 0.2024 -0.0225 -0.3221 0.207 Uiso 1 1 calc R . . C16 C -0.0511(6) -0.2594(10) -0.3006(9) 0.151(6) Uani 1 1 d . . . H16A H 0.0003 -0.2919 -0.2564 0.227 Uiso 1 1 calc R . . H16B H -0.0830 -0.2970 -0.3558 0.227 Uiso 1 1 calc R . . H16C H -0.0883 -0.2455 -0.2708 0.227 Uiso 1 1 calc R . . C17 C 0.3657(4) -0.0409(5) 0.0095(5) 0.0686(18) Uani 1 1 d . . . C18 C 0.3248(4) -0.0989(4) 0.0442(5) 0.0650(17) Uani 1 1 d . . . H18A H 0.3053 -0.0781 0.0875 0.078 Uiso 1 1 calc R . . C19 C 0.3126(4) -0.1891(4) 0.0147(4) 0.0559(15) Uani 1 1 d . . . H19A H 0.2849 -0.2288 0.0392 0.067 Uiso 1 1 calc R . . C20 C 0.3399(3) -0.2224(4) -0.0496(4) 0.0458(13) Uani 1 1 d . . . C21 C 0.3807(4) -0.1615(4) -0.0846(5) 0.0603(16) Uani 1 1 d . . . H21A H 0.3996 -0.1815 -0.1288 0.072 Uiso 1 1 calc R . . C22 C 0.3939(5) -0.0708(4) -0.0544(5) 0.0722(19) Uani 1 1 d . . . H22A H 0.4220 -0.0304 -0.0779 0.087 Uiso 1 1 calc R . . C23 C 0.5300(4) -0.3311(4) -0.1157(4) 0.0513(14) Uani 1 1 d . . . C24 C 0.4983(4) -0.3228(5) -0.2112(5) 0.0686(18) Uani 1 1 d . . . H24A H 0.4376 -0.3245 -0.2493 0.082 Uiso 1 1 calc R . . C25 C 0.5543(5) -0.3116(5) -0.2543(5) 0.080(2) Uani 1 1 d . . . H25A H 0.5307 -0.3059 -0.3202 0.096 Uiso 1 1 calc R . . C26 C 0.6437(5) -0.3089(4) -0.1993(5) 0.0655(18) Uani 1 1 d . . . C27 C 0.6747(5) -0.3163(5) -0.1031(5) 0.0690(18) Uani 1 1 d . . . H27A H 0.7352 -0.3138 -0.0644 0.083 Uiso 1 1 calc R . . C28 C 0.6193(4) -0.3271(5) -0.0619(5) 0.0648(17) Uani 1 1 d . . . H28A H 0.6430 -0.3319 0.0041 0.078 Uiso 1 1 calc R . . C29 C 0.6778(8) -0.3159(8) -0.3284(9) 0.146(4) Uani 1 1 d . . . H29A H 0.7258 -0.3054 -0.3439 0.219 Uiso 1 1 calc R . . H29B H 0.6295 -0.2762 -0.3661 0.219 Uiso 1 1 calc R . . H29C H 0.6591 -0.3787 -0.3415 0.219 Uiso 1 1 calc R . . C30 C 0.3838(4) -0.3606(4) -0.1229(4) 0.0478(14) Uani 1 1 d . . . H30A H 0.3650 -0.3329 -0.1860 0.057 Uiso 1 1 calc R . . C31 C 0.3718(4) -0.4640(4) -0.1378(5) 0.0591(16) Uani 1 1 d . . . C32 C 0.3376(7) -0.5875(5) -0.2429(6) 0.103(3) Uani 1 1 d . . . H32A H 0.3179 -0.5995 -0.3096 0.154 Uiso 1 1 calc R . . H32B H 0.2952 -0.6111 -0.2237 0.154 Uiso 1 1 calc R . . H32C H 0.3935 -0.6168 -0.2067 0.154 Uiso 1 1 calc R . . C33 C 0.3217(3) -0.3223(4) -0.0826(4) 0.0467(13) Uani 1 1 d . . . C34 C 0.3250(4) -0.3801(4) 0.0013(4) 0.0536(15) Uani 1 1 d . . . C35 C 0.4121(5) -0.4237(5) 0.1605(4) 0.079(2) Uani 1 1 d . . . H35A H 0.4715 -0.4183 0.2099 0.118 Uiso 1 1 calc R . . H35B H 0.3974 -0.4875 0.1467 0.118 Uiso 1 1 calc R . . H35C H 0.3723 -0.3961 0.1814 0.118 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 Br1 0.1359(9) 0.0596(5) 0.1598(10) -0.0325(5) 0.0852(8) -0.0203(5) P1 0.0459(9) 0.0613(10) 0.0406(8) 0.0020(7) 0.0133(7) 0.0009(7) O1 0.054(2) 0.080(3) 0.047(2) -0.002(2) 0.012(2) 0.015(2) O2 0.043(2) 0.083(3) 0.041(2) -0.005(2) 0.0152(18) -0.005(2) O3 0.052(2) 0.069(3) 0.052(2) 0.009(2) 0.019(2) -0.002(2) O4 0.064(3) 0.080(3) 0.062(3) 0.013(2) 0.020(2) -0.022(3) O5 0.057(3) 0.070(3) 0.038(2) 0.010(2) 0.010(2) -0.001(2) O6 0.177(6) 0.053(3) 0.075(3) 0.018(3) 0.040(4) 0.008(3) O7 0.115(4) 0.052(3) 0.076(3) -0.013(2) 0.044(3) -0.010(3) O8 0.118(4) 0.099(4) 0.101(4) 0.013(3) 0.076(4) -0.005(3) N1 0.046(3) 0.055(3) 0.042(3) 0.004(2) 0.008(2) -0.008(2) N2 0.047(3) 0.070(3) 0.044(3) -0.001(2) 0.013(2) 0.003(2) C1 0.051(4) 0.095(5) 0.043(4) -0.003(4) 0.016(3) -0.015(4) C2 0.076(5) 0.129(8) 0.052(4) -0.021(5) 0.031(4) -0.037(5) C3 0.091(6) 0.120(8) 0.077(6) -0.042(5) 0.049(5) -0.037(5) C4 0.086(6) 0.084(5) 0.094(6) -0.033(5) 0.042(5) -0.031(4) C5 0.059(4) 0.071(5) 0.060(4) -0.012(4) 0.023(3) -0.020(3) C6 0.041(3) 0.085(5) 0.045(3) -0.013(3) 0.016(3) -0.017(3) C7 0.088(5) 0.084(5) 0.073(5) 0.002(4) 0.026(4) -0.028(4) C8 0.085(5) 0.109(7) 0.060(4) 0.022(4) 0.020(4) -0.003(5) C9 0.134(9) 0.101(7) 0.082(6) 0.033(5) 0.050(6) 0.068(7) C10 0.204(14) 0.176(12) 0.099(8) 0.058(8) 0.086(9) 0.114(11) C11 0.121(14) 0.36(3) 0.064(7) 0.007(12) 0.028(8) 0.143(18) C12 0.111(11) 0.30(2) 0.075(9) -0.041(12) 0.033(7) 0.081(14) C13 0.061(6) 0.203(12) 0.068(5) -0.051(7) 0.018(5) 0.038(7) C14 0.064(5) 0.120(7) 0.042(4) -0.010(4) 0.012(3) 0.036(5) C15 0.149(11) 0.079(7) 0.191(12) 0.036(7) 0.080(9) 0.027(7) C16 0.059(6) 0.242(16) 0.158(10) -0.107(11) 0.053(6) -0.036(8) C17 0.060(4) 0.054(4) 0.092(5) -0.019(4) 0.034(4) -0.009(3) C18 0.062(4) 0.062(4) 0.074(4) -0.009(3) 0.033(4) 0.002(3) C19 0.053(4) 0.059(4) 0.060(4) -0.003(3) 0.028(3) -0.006(3) C20 0.034(3) 0.047(3) 0.047(3) 0.004(3) 0.009(3) 0.001(2) C21 0.062(4) 0.053(4) 0.070(4) 0.003(3) 0.033(3) -0.001(3) C22 0.078(5) 0.051(4) 0.096(5) 0.000(4) 0.047(4) -0.010(3) C23 0.053(4) 0.044(3) 0.051(3) 0.004(3) 0.019(3) 0.004(3) C24 0.055(4) 0.083(5) 0.061(4) 0.007(4) 0.020(3) -0.009(4) C25 0.098(6) 0.085(5) 0.060(4) 0.008(4) 0.037(4) -0.010(4) C26 0.075(5) 0.048(4) 0.086(5) 0.004(3) 0.048(4) -0.001(3) C27 0.057(4) 0.070(4) 0.077(5) 0.012(4) 0.027(4) 0.011(3) C28 0.061(4) 0.071(4) 0.060(4) 0.006(3) 0.025(3) 0.004(3) C29 0.190(12) 0.125(9) 0.175(12) 0.020(8) 0.128(11) 0.011(8) C30 0.047(3) 0.046(3) 0.042(3) 0.002(3) 0.012(3) 0.001(3) C31 0.061(4) 0.050(4) 0.060(4) -0.001(3) 0.022(3) 0.003(3) C32 0.147(8) 0.055(4) 0.110(7) -0.023(4) 0.060(6) -0.011(5) C33 0.042(3) 0.049(3) 0.042(3) 0.000(3) 0.013(3) -0.002(3) C34 0.057(4) 0.048(3) 0.046(3) 0.004(3) 0.014(3) 0.000(3) C35 0.085(5) 0.094(5) 0.041(4) 0.014(4) 0.013(3) -0.001(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 Br1 C17 1.903(7) . ? P1 O3 1.449(4) . ? P1 O1 1.579(4) . ? P1 O2 1.581(4) . ? P1 N1 1.633(5) . ? O1 C14 1.433(8) . ? O2 C6 1.404(7) . ? O4 C34 1.184(7) . ? O5 C34 1.327(7) . ? O5 C35 1.451(7) . ? O6 C31 1.180(7) . ? O7 C31 1.305(7) . ? O7 C32 1.458(8) . ? O8 C29 1.374(12) . ? O8 C26 1.376(8) . ? N1 C33 1.481(7) . ? N1 H1A 0.8600 . ? N2 C23 1.421(7) . ? N2 C30 1.431(7) . ? N2 H2A 0.8600 . ? C1 C2 1.390(10) . ? C1 C6 1.409(9) . ? C1 C8 1.483(10) . ? C2 C3 1.339(12) . ? C2 H2B 0.9300 . ? C3 C4 1.377(11) . ? C3 H3B 0.9300 . ? C4 C5 1.387(10) . ? C4 H4A 0.9300 . ? C5 C6 1.372(9) . ? C5 C7 1.499(9) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C14 1.398(13) . ? C9 C10 1.410(13) . ? C9 C15 1.466(14) . ? C10 C11 1.38(2) . ? C10 H10A 0.9300 . ? C11 C12 1.30(3) . ? C11 H11A 0.9300 . ? C12 C13 1.461(19) . ? C12 H12A 0.9300 . ? C13 C14 1.362(12) . ? C13 C16 1.502(16) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.351(9) . ? C17 C22 1.361(9) . ? C18 C19 1.377(9) . ? C18 H18A 0.9300 . ? C19 C20 1.372(8) . ? C19 H19A 0.9300 . ? C20 C21 1.382(8) . ? C20 C33 1.529(8) . ? C21 C22 1.388(9) . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? C23 C24 1.351(8) . ? C23 C28 1.364(8) . ? C24 C25 1.399(9) . ? C24 H24A 0.9300 . ? C25 C26 1.368(10) . ? C25 H25A 0.9300 . ? C26 C27 1.361(9) . ? C27 C28 1.366(9) . ? C27 H27A 0.9300 . ? C28 H28A 0.9300 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 C31 1.524(8) . ? C30 C33 1.553(8) . ? C30 H30A 0.9800 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.543(8) . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? 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 O3 P1 O1 117.2(3) . . ? O3 P1 O2 115.8(2) . . ? O1 P1 O2 99.4(2) . . ? O3 P1 N1 113.7(2) . . ? O1 P1 N1 103.2(2) . . ? O2 P1 N1 105.8(2) . . ? C14 O1 P1 125.1(4) . . ? C6 O2 P1 123.8(3) . . ? C34 O5 C35 115.4(5) . . ? C31 O7 C32 114.9(6) . . ? C29 O8 C26 116.9(7) . . ? C33 N1 P1 125.6(4) . . ? C33 N1 H1A 117.2 . . ? P1 N1 H1A 117.2 . . ? C23 N2 C30 119.8(5) . . ? C23 N2 H2A 120.1 . . ? C30 N2 H2A 120.1 . . ? C2 C1 C6 115.0(7) . . ? C2 C1 C8 121.9(7) . . ? C6 C1 C8 123.1(6) . . ? C3 C2 C1 122.6(7) . . ? C3 C2 H2B 118.7 . . ? C1 C2 H2B 118.7 . . ? C2 C3 C4 120.6(8) . . ? C2 C3 H3B 119.7 . . ? C4 C3 H3B 119.7 . . ? C3 C4 C5 120.7(8) . . ? C3 C4 H4A 119.7 . . ? C5 C4 H4A 119.7 . . ? C6 C5 C4 116.9(7) . . ? C6 C5 C7 121.6(6) . . ? C4 C5 C7 121.4(7) . . ? C5 C6 O2 117.8(6) . . ? C5 C6 C1 124.0(6) . . ? O2 C6 C1 117.9(6) . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C1 C8 H8A 109.5 . . ? C1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C9 C10 114.3(12) . . ? C14 C9 C15 122.9(7) . . ? C10 C9 C15 122.8(12) . . ? C11 C10 C9 118.0(15) . . ? C11 C10 H10A 121.0 . . ? C9 C10 H10A 121.0 . . ? C12 C11 C10 128.1(19) . . ? C12 C11 H11A 116.0 . . ? C10 C11 H11A 116.0 . . ? C11 C12 C13 116.1(19) . . ? C11 C12 H12A 121.9 . . ? C13 C12 H12A 121.9 . . ? C14 C13 C12 116.2(14) . . ? C14 C13 C16 124.6(10) . . ? C12 C13 C16 119.1(12) . . ? C13 C14 C9 127.0(9) . . ? C13 C14 O1 115.4(9) . . ? C9 C14 O1 117.3(7) . . ? C9 C15 H15A 109.5 . . ? C9 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C9 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C22 120.6(6) . . ? C18 C17 Br1 119.7(5) . . ? C22 C17 Br1 119.7(5) . . ? C17 C18 C19 119.2(6) . . ? C17 C18 H18A 120.4 . . ? C19 C18 H18A 120.4 . . ? C20 C19 C18 122.3(6) . . ? C20 C19 H19A 118.9 . . ? C18 C19 H19A 118.9 . . ? C19 C20 C21 117.4(5) . . ? C19 C20 C33 120.2(5) . . ? C21 C20 C33 122.4(5) . . ? C20 C21 C22 120.5(6) . . ? C20 C21 H21A 119.7 . . ? C22 C21 H21A 119.7 . . ? C17 C22 C21 120.0(6) . . ? C17 C22 H22A 120.0 . . ? C21 C22 H22A 120.0 . . ? C24 C23 C28 117.5(6) . . ? C24 C23 N2 123.8(6) . . ? C28 C23 N2 118.7(5) . . ? C23 C24 C25 121.8(6) . . ? C23 C24 H24A 119.1 . . ? C25 C24 H24A 119.1 . . ? C26 C25 C24 119.9(7) . . ? C26 C25 H25A 120.1 . . ? C24 C25 H25A 120.1 . . ? C27 C26 C25 117.7(7) . . ? C27 C26 O8 117.1(7) . . ? C25 C26 O8 125.2(7) . . ? C26 C27 C28 121.9(7) . . ? C26 C27 H27A 119.1 . . ? C28 C27 H27A 119.1 . . ? C23 C28 C27 121.2(6) . . ? C23 C28 H28A 119.4 . . ? C27 C28 H28A 119.4 . . ? O8 C29 H29A 109.5 . . ? O8 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? O8 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N2 C30 C31 109.2(5) . . ? N2 C30 C33 116.1(4) . . ? C31 C30 C33 110.4(5) . . ? N2 C30 H30A 106.9 . . ? C31 C30 H30A 106.9 . . ? C33 C30 H30A 106.9 . . ? O6 C31 O7 122.7(6) . . ? O6 C31 C30 124.1(6) . . ? O7 C31 C30 113.1(6) . . ? O7 C32 H32A 109.5 . . ? O7 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? O7 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? N1 C33 C20 112.7(4) . . ? N1 C33 C34 103.4(4) . . ? C20 C33 C34 107.7(4) . . ? N1 C33 C30 106.1(4) . . ? C20 C33 C30 114.1(4) . . ? C34 C33 C30 112.3(5) . . ? O4 C34 O5 124.4(5) . . ? O4 C34 C33 124.2(5) . . ? O5 C34 C33 111.4(5) . . ? O5 C35 H35A 109.5 . . ? O5 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? O5 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 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 O3 P1 O1 C14 64.6(6) . . . . ? O2 P1 O1 C14 -61.0(6) . . . . ? N1 P1 O1 C14 -169.8(6) . . . . ? O3 P1 O2 C6 30.9(5) . . . . ? O1 P1 O2 C6 157.4(5) . . . . ? N1 P1 O2 C6 -95.9(5) . . . . ? O3 P1 N1 C33 31.2(5) . . . . ? O1 P1 N1 C33 -96.7(5) . . . . ? O2 P1 N1 C33 159.3(4) . . . . ? C6 C1 C2 C3 1.9(10) . . . . ? C8 C1 C2 C3 -175.7(8) . . . . ? C1 C2 C3 C4 1.2(13) . . . . ? C2 C3 C4 C5 -2.4(12) . . . . ? C3 C4 C5 C6 0.2(10) . . . . ? C3 C4 C5 C7 176.1(7) . . . . ? C4 C5 C6 O2 176.9(5) . . . . ? C7 C5 C6 O2 1.0(9) . . . . ? C4 C5 C6 C1 3.2(10) . . . . ? C7 C5 C6 C1 -172.7(6) . . . . ? P1 O2 C6 C5 104.9(6) . . . . ? P1 O2 C6 C1 -81.1(6) . . . . ? C2 C1 C6 C5 -4.2(9) . . . . ? C8 C1 C6 C5 173.3(6) . . . . ? C2 C1 C6 O2 -177.9(5) . . . . ? C8 C1 C6 O2 -0.3(9) . . . . ? C14 C9 C10 C11 0.1(14) . . . . ? C15 C9 C10 C11 -179.2(11) . . . . ? C9 C10 C11 C12 6(3) . . . . ? C10 C11 C12 C13 -7(3) . . . . ? C11 C12 C13 C14 2.8(19) . . . . ? C11 C12 C13 C16 179.7(14) . . . . ? C12 C13 C14 C9 2.6(12) . . . . ? C16 C13 C14 C9 -174.1(8) . . . . ? C12 C13 C14 O1 175.8(8) . . . . ? C16 C13 C14 O1 -0.9(11) . . . . ? C10 C9 C14 C13 -4.0(12) . . . . ? C15 C9 C14 C13 175.4(9) . . . . ? C10 C9 C14 O1 -177.1(7) . . . . ? C15 C9 C14 O1 2.3(12) . . . . ? P1 O1 C14 C13 98.5(7) . . . . ? P1 O1 C14 C9 -87.6(7) . . . . ? C22 C17 C18 C19 0.5(11) . . . . ? Br1 C17 C18 C19 -179.5(5) . . . . ? C17 C18 C19 C20 -0.5(10) . . . . ? C18 C19 C20 C21 -0.1(9) . . . . ? C18 C19 C20 C33 -177.8(5) . . . . ? C19 C20 C21 C22 0.7(9) . . . . ? C33 C20 C21 C22 178.3(6) . . . . ? C18 C17 C22 C21 0.1(11) . . . . ? Br1 C17 C22 C21 -179.9(5) . . . . ? C20 C21 C22 C17 -0.7(10) . . . . ? C30 N2 C23 C24 13.1(9) . . . . ? C30 N2 C23 C28 -169.2(6) . . . . ? C28 C23 C24 C25 0.7(10) . . . . ? N2 C23 C24 C25 178.5(6) . . . . ? C23 C24 C25 C26 0.1(11) . . . . ? C24 C25 C26 C27 -0.9(11) . . . . ? C24 C25 C26 O8 -179.6(7) . . . . ? C29 O8 C26 C27 162.3(8) . . . . ? C29 O8 C26 C25 -18.9(11) . . . . ? C25 C26 C27 C28 0.9(11) . . . . ? O8 C26 C27 C28 179.7(6) . . . . ? C24 C23 C28 C27 -0.8(10) . . . . ? N2 C23 C28 C27 -178.6(6) . . . . ? C26 C27 C28 C23 0.0(11) . . . . ? C23 N2 C30 C31 84.7(6) . . . . ? C23 N2 C30 C33 -149.7(5) . . . . ? C32 O7 C31 O6 0.0(11) . . . . ? C32 O7 C31 C30 178.0(6) . . . . ? N2 C30 C31 O6 67.3(9) . . . . ? C33 C30 C31 O6 -61.5(8) . . . . ? N2 C30 C31 O7 -110.7(6) . . . . ? C33 C30 C31 O7 120.5(6) . . . . ? P1 N1 C33 C20 50.8(6) . . . . ? P1 N1 C33 C34 166.9(4) . . . . ? P1 N1 C33 C30 -74.8(5) . . . . ? C19 C20 C33 N1 80.7(6) . . . . ? C21 C20 C33 N1 -96.9(6) . . . . ? C19 C20 C33 C34 -32.8(7) . . . . ? C21 C20 C33 C34 149.7(5) . . . . ? C19 C20 C33 C30 -158.2(5) . . . . ? C21 C20 C33 C30 24.2(7) . . . . ? N2 C30 C33 N1 169.9(4) . . . . ? C31 C30 C33 N1 -65.1(6) . . . . ? N2 C30 C33 C20 45.2(6) . . . . ? C31 C30 C33 C20 170.2(5) . . . . ? N2 C30 C33 C34 -77.8(6) . . . . ? C31 C30 C33 C34 47.2(6) . . . . ? C35 O5 C34 O4 -2.0(9) . . . . ? C35 O5 C34 C33 175.2(5) . . . . ? N1 C33 C34 O4 -5.2(8) . . . . ? C20 C33 C34 O4 114.4(6) . . . . ? C30 C33 C34 O4 -119.1(7) . . . . ? N1 C33 C34 O5 177.7(5) . . . . ? C20 C33 C34 O5 -62.8(6) . . . . ? C30 C33 C34 O5 63.8(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.826 _refine_diff_density_min -1.293 _refine_diff_density_rms 0.072