Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Willem van der Donk' _publ_contact_author_address ; Department of Chemistry University of Illinois - Urbana-Champaign 600 South Matthews Avenue Urbana Illinois 61801 UNITED STATES OF AMERICA ; _publ_contact_author_email VDDONK@UIUC.EDU _publ_section_title ; Model Studies of the CuB Site of Cytochrome c Oxidase Utilizing a Zn(II) Complex Containing an Imidazole-Phenol Cross-Linked Ligand ; loop_ _publ_author_name 'W.Van Der Donk' 'Jerry Jeffers' 'Russell Pesavento' 'Derek A. Pratt' # Attachment 'B516090A revised CIF.doc' data_f80tface _database_code_depnum_ccdc_archive 'CCDC 290020' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common BPAIP.4HBr _chemical_melting_point ? _chemical_formula_moiety '2(C25 H31 N5 O), C H4 O2, 2(C H4 O), 8(Br)' _chemical_formula_sum 'C53 H74 Br8 N10 O6' _chemical_formula_weight 1586.50 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' 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)/n _symmetry_space_group_name_Hall -P2yn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.088(7) _cell_length_b 7.523(4) _cell_length_c 34.712(17) _cell_angle_alpha 90.00 _cell_angle_beta 97.751(10) _cell_angle_gamma 90.00 _cell_volume 3645(3) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 866 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 21.36 _exptl_crystal_description platy _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1580 _exptl_absorpt_coefficient_mu 4.446 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.3603 _exptl_absorpt_correction_T_max 0.8811 _exptl_absorpt_process_details Face-Indexed _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 34095 _diffrn_reflns_av_R_equivalents 0.2790 _diffrn_reflns_av_sigmaI/netI 0.1992 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6388 _reflns_number_gt 3006 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1054P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6388 _refine_ls_number_parameters 365 _refine_ls_number_restraints 23 _refine_ls_R_factor_all 0.1896 _refine_ls_R_factor_gt 0.0866 _refine_ls_wR_factor_ref 0.2255 _refine_ls_wR_factor_gt 0.1898 _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_restrained_S_all 0.962 _refine_ls_shift/su_max 0.003 _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 O10 O 0.8855(7) 1.0013(10) 0.7092(2) 0.051(2) Uani 1 1 d . . . H10 H 0.9085 0.9528 0.6908 0.077 Uiso 1 1 calc R . . C11 C 0.6566(12) 1.2071(18) 0.7136(4) 0.064(4) Uani 1 1 d . . . H11 H 0.6231 1.2577 0.7329 0.077 Uiso 1 1 calc R . . C12 C 0.6122(11) 1.2003(17) 0.6746(4) 0.057(4) Uani 1 1 d . . . H12 H 0.5491 1.2440 0.6671 0.069 Uiso 1 1 calc R . . C13 C 0.6663(12) 1.1251(18) 0.6471(3) 0.058(4) Uani 1 1 d . . . H13 H 0.6393 1.1203 0.6205 0.070 Uiso 1 1 calc R . . C14 C 0.7561(11) 1.0595(16) 0.6579(4) 0.048(4) Uani 1 1 d . . . H14 H 0.7895 1.0066 0.6389 0.058 Uiso 1 1 calc R . . C15 C 0.7998(10) 1.0685(15) 0.6963(3) 0.041(3) Uani 1 1 d . . . C16 C 0.7459(10) 1.1431(15) 0.7239(3) 0.040(3) Uani 1 1 d . . . N21 N 0.8210(8) 0.7320(13) 1.0382(3) 0.049(3) Uani 1 1 d . . . H21 H 0.7609 0.7487 1.0416 0.059 Uiso 1 1 calc R . . C22 C 0.8747(12) 0.6249(18) 1.0622(4) 0.057(4) Uani 1 1 d . . . H22 H 0.8482 0.5671 1.0826 0.069 Uiso 1 1 calc R . . C23 C 0.9679(13) 0.5976(19) 1.0575(4) 0.071(5) Uani 1 1 d . . . H23 H 1.0079 0.5231 1.0749 0.085 Uiso 1 1 calc R . . C24 C 1.0032(10) 0.6819(13) 1.0266(4) 0.054(4) Uani 1 1 d . . . H24 H 1.0678 0.6637 1.0225 0.065 Uiso 1 1 calc R . . C25 C 0.9456(9) 0.7898(15) 1.0023(3) 0.037(3) Uani 1 1 d . . . H25 H 0.9702 0.8449 0.9811 0.044 Uiso 1 1 calc R . . C26 C 0.8561(9) 0.8191(14) 1.0078(3) 0.033(3) Uani 1 1 d . . . N31 N 0.4609(7) 0.7453(11) 0.9549(3) 0.038(2) Uani 1 1 d . . . H31 H 0.5111 0.7244 0.9723 0.046 Uiso 1 1 calc R . . C32 C 0.3736(12) 0.7187(15) 0.9648(4) 0.055(4) Uani 1 1 d . . . H32 H 0.3680 0.6748 0.9901 0.066 Uiso 1 1 calc R . . C33 C 0.2928(10) 0.7523(17) 0.9401(4) 0.053(4) Uani 1 1 d . . . H33 H 0.2308 0.7360 0.9474 0.063 Uiso 1 1 calc R . . C34 C 0.3058(9) 0.8102(19) 0.9044(4) 0.057(4) Uani 1 1 d . . . H34 H 0.2502 0.8355 0.8865 0.069 Uiso 1 1 calc R . . C35 C 0.3920(10) 0.8350(17) 0.8921(4) 0.052(4) Uani 1 1 d . . . H35 H 0.3968 0.8724 0.8663 0.063 Uiso 1 1 calc R . . C36 C 0.4753(10) 0.8031(14) 0.9192(3) 0.042(3) Uani 1 1 d . . . N41 N 0.7927(8) 1.1608(12) 0.7631(2) 0.037(2) Uani 1 1 d . . . C42 C 0.8808(10) 1.2181(15) 0.7740(3) 0.048(4) Uani 1 1 d . . . H42 H 0.9239 1.2584 0.7571 0.058 Uiso 1 1 calc R . . N43 N 0.8991(7) 1.2101(12) 0.8120(2) 0.042(3) Uani 1 1 d . . . H43 H 0.9538 1.2389 0.8260 0.050 Uiso 1 1 calc R . . C44 C 0.8188(9) 1.1493(14) 0.8265(3) 0.034(3) Uani 1 1 d . . . C45 C 0.7520(8) 1.1200(12) 0.7961(3) 0.026(3) Uani 1 1 d . . . H45 H 0.6885 1.0789 0.7970 0.031 Uiso 1 1 calc R . . C51 C 0.8188(8) 1.1245(14) 0.8692(3) 0.032(3) Uani 1 1 d . . . H51A H 0.8722 1.0450 0.8796 0.038 Uiso 1 1 calc R . . H51B H 0.8286 1.2406 0.8825 0.038 Uiso 1 1 calc R . . C52 C 0.7261(8) 1.0458(15) 0.8770(3) 0.032(3) Uani 1 1 d . . . H52A H 0.7208 0.9237 0.8663 0.039 Uiso 1 1 calc R . . H52B H 0.6728 1.1167 0.8632 0.039 Uiso 1 1 calc R . . N53 N 0.7154(6) 1.0390(11) 0.9197(2) 0.028(2) Uani 1 1 d . . . H53 H 0.7307 1.1520 0.9294 0.034 Uiso 1 1 calc R . . C62 C 0.6139(8) 1.0072(14) 0.9256(3) 0.032(3) Uani 1 1 d . . . H62A H 0.5732 1.1004 0.9116 0.039 Uiso 1 1 calc R . . H62B H 0.6086 1.0189 0.9536 0.039 Uiso 1 1 calc R . . C61 C 0.5757(8) 0.8255(15) 0.9116(3) 0.034(3) Uani 1 1 d . . . H61A H 0.5786 0.8138 0.8833 0.041 Uiso 1 1 calc R . . H61B H 0.6162 0.7311 0.9252 0.041 Uiso 1 1 calc R . . C71 C 0.7878(9) 0.9417(16) 0.9857(3) 0.041(3) Uani 1 1 d . . . H71A H 0.8068 1.0655 0.9927 0.049 Uiso 1 1 calc R . . H71B H 0.7233 0.9217 0.9932 0.049 Uiso 1 1 calc R . . C72 C 0.7833(8) 0.9178(14) 0.9416(3) 0.029(3) Uani 1 1 d . . . H72A H 0.8478 0.9382 0.9342 0.035 Uiso 1 1 calc R . . H72B H 0.7646 0.7939 0.9347 0.035 Uiso 1 1 calc R . . C81 C 0.4499(14) 0.394(2) 0.8556(5) 0.125(8) Uani 1 1 d D . . H81A H 0.3918 0.3452 0.8406 0.187 Uiso 1 1 calc R . . H81B H 0.4512 0.5232 0.8519 0.187 Uiso 1 1 calc R . . H81C H 0.4503 0.3672 0.8832 0.187 Uiso 1 1 calc R . . O82 O 0.5328(6) 0.3161(12) 0.8422(3) 0.060(3) Uani 1 1 d D . . H82 H 0.5219 0.2086 0.8368 0.089 Uiso 1 1 calc R . . Br1 Br 0.73931(9) 0.43637(15) 0.95087(3) 0.0366(4) Uani 1 1 d . . . Br2 Br 0.40834(10) 0.24259(17) 0.96164(3) 0.0471(4) Uani 1 1 d . . . Br3 Br 0.04769(9) 0.88357(17) 0.91271(4) 0.0479(4) Uani 1 1 d . . . Br4 Br 0.49940(11) 0.9470(2) 0.79951(4) 0.0660(5) Uani 1 1 d . . . O83 O 1.0773(16) 1.349(4) 0.8404(6) 0.083(8) Uani 0.50 1 d PDU A 1 O84 O 1.0669(16) 1.225(3) 0.8542(7) 0.090(8) Uani 0.50 1 d PDU B 2 H84 H 1.0542 1.1706 0.8740 0.134 Uiso 0.50 1 calc PR B 2 C82 C 1.166(2) 1.203(5) 0.8507(11) 0.114(13) Uani 0.50 1 d PDU B 2 H82A H 1.1872 1.3025 0.8358 0.171 Uiso 0.50 1 calc PR B 2 H82B H 1.1748 1.0912 0.8372 0.171 Uiso 0.50 1 calc PR B 2 H82C H 1.2030 1.2006 0.8766 0.171 Uiso 0.50 1 calc PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O10 0.075(7) 0.059(6) 0.024(5) -0.002(4) 0.021(5) 0.002(5) C11 0.083(13) 0.051(10) 0.062(11) 0.017(8) 0.017(9) -0.011(9) C12 0.081(11) 0.055(9) 0.033(8) 0.007(7) -0.003(8) -0.022(8) C13 0.100(13) 0.058(9) 0.014(7) -0.008(6) -0.005(8) -0.034(9) C14 0.069(11) 0.045(8) 0.032(8) -0.011(6) 0.016(7) -0.025(8) C15 0.069(10) 0.032(7) 0.022(7) 0.002(6) 0.009(7) -0.010(7) C16 0.058(9) 0.035(7) 0.031(8) 0.005(6) 0.015(7) 0.002(7) N21 0.060(8) 0.056(7) 0.033(6) 0.013(6) 0.013(6) -0.006(6) C22 0.081(12) 0.054(9) 0.034(8) 0.017(7) -0.001(8) -0.009(9) C23 0.075(13) 0.073(12) 0.053(10) 0.007(8) -0.034(10) 0.010(10) C24 0.037(9) 0.064(10) 0.061(10) -0.030(8) 0.001(8) 0.004(8) C25 0.037(8) 0.034(7) 0.040(8) -0.001(6) 0.007(6) 0.014(6) C26 0.048(9) 0.030(7) 0.021(6) 0.001(5) 0.009(6) 0.002(6) N31 0.045(7) 0.033(6) 0.037(6) -0.003(5) 0.008(5) -0.006(5) C32 0.080(12) 0.033(8) 0.067(10) -0.024(7) 0.062(10) -0.014(8) C33 0.042(9) 0.052(9) 0.068(11) -0.027(8) 0.024(8) -0.007(7) C34 0.027(8) 0.087(11) 0.061(10) -0.023(8) 0.015(7) -0.006(8) C35 0.052(10) 0.063(9) 0.036(8) -0.011(7) -0.015(8) -0.007(8) C36 0.076(10) 0.027(7) 0.029(7) -0.015(5) 0.031(7) -0.016(7) N41 0.058(7) 0.043(6) 0.011(5) 0.001(4) 0.014(5) -0.007(6) C42 0.069(10) 0.054(9) 0.026(8) -0.006(6) 0.025(7) -0.012(8) N43 0.052(7) 0.063(7) 0.011(5) -0.004(5) 0.013(5) -0.006(6) C44 0.039(8) 0.028(7) 0.036(8) -0.002(6) 0.009(7) 0.001(6) C45 0.042(7) 0.019(6) 0.020(6) -0.002(5) 0.017(6) -0.001(5) C51 0.041(7) 0.037(7) 0.022(6) -0.008(5) 0.022(5) -0.002(6) C52 0.038(7) 0.040(7) 0.021(6) -0.004(5) 0.015(5) -0.004(6) N53 0.041(6) 0.027(5) 0.022(5) -0.006(4) 0.020(4) 0.000(5) C62 0.042(8) 0.037(7) 0.019(6) -0.007(5) 0.010(6) 0.008(6) C61 0.036(8) 0.040(7) 0.029(7) -0.006(6) 0.014(6) 0.007(6) C71 0.054(9) 0.054(8) 0.018(6) -0.001(6) 0.021(6) 0.015(7) C72 0.046(8) 0.026(6) 0.018(6) 0.000(5) 0.017(5) 0.012(6) C81 0.18(2) 0.118(17) 0.097(14) -0.007(12) 0.078(14) 0.045(15) O82 0.079(7) 0.056(6) 0.053(6) 0.017(5) 0.044(5) 0.006(5) Br1 0.0544(8) 0.0311(7) 0.0273(7) 0.0013(5) 0.0164(6) -0.0005(6) Br2 0.0556(9) 0.0545(8) 0.0360(8) -0.0050(6) 0.0231(6) 0.0030(7) Br3 0.0444(9) 0.0523(9) 0.0483(8) -0.0055(6) 0.0111(7) 0.0004(7) Br4 0.0833(12) 0.0755(11) 0.0459(9) -0.0165(8) 0.0327(8) -0.0022(9) O83 0.077(17) 0.13(2) 0.033(12) 0.006(13) -0.006(11) -0.023(16) O84 0.071(17) 0.13(2) 0.070(17) 0.012(15) 0.012(13) -0.035(16) C82 0.109(15) 0.122(16) 0.115(15) -0.003(10) 0.028(10) 0.001(10) _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 O10 C15 1.330(14) . ? O10 H10 0.8400 . ? C11 C16 1.350(17) . ? C11 C12 1.414(17) . ? C11 H11 0.9500 . ? C12 C13 1.416(18) . ? C12 H12 0.9500 . ? C13 C14 1.362(18) . ? C13 H13 0.9500 . ? C14 C15 1.391(16) . ? C14 H14 0.9500 . ? C15 C16 1.416(16) . ? C16 N41 1.438(14) . ? N21 C22 1.321(15) . ? N21 C26 1.388(14) . ? N21 H21 0.8800 . ? C22 C23 1.360(19) . ? C22 H22 0.9500 . ? C23 C24 1.394(19) . ? C23 H23 0.9500 . ? C24 C25 1.358(16) . ? C24 H24 0.9500 . ? C25 C26 1.319(15) . ? C25 H25 0.9500 . ? C26 C71 1.471(15) . ? N31 C32 1.336(15) . ? N31 C36 1.353(13) . ? N31 H31 0.8800 . ? C32 C33 1.353(18) . ? C32 H32 0.9500 . ? C33 C34 1.350(18) . ? C33 H33 0.9500 . ? C34 C35 1.354(17) . ? C34 H34 0.9500 . ? C35 C36 1.423(16) . ? C35 H35 0.9500 . ? C36 C61 1.483(15) . ? N41 C42 1.320(14) . ? N41 C45 1.383(12) . ? C42 N43 1.311(12) . ? C42 H42 0.9500 . ? N43 C44 1.376(14) . ? N43 H43 0.8800 . ? C44 C45 1.334(14) . ? C44 C51 1.493(14) . ? C45 H45 0.9500 . ? C51 C52 1.491(14) . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? C52 N53 1.511(12) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? N53 C72 1.460(12) . ? N53 C62 1.490(13) . ? N53 H53 0.9300 . ? C62 C61 1.525(15) . ? C62 H62A 0.9900 . ? C62 H62B 0.9900 . ? C61 H61A 0.9900 . ? C61 H61B 0.9900 . ? C71 C72 1.534(13) . ? C71 H71A 0.9900 . ? C71 H71B 0.9900 . ? C72 H72A 0.9900 . ? C72 H72B 0.9900 . ? C81 O82 1.438(16) . ? C81 H81A 0.9800 . ? C81 H81B 0.9800 . ? C81 H81C 0.9800 . ? O82 H82 0.8400 . ? O84 C82 1.42(2) . ? O84 H84 0.8400 . ? C82 H82A 0.9800 . ? C82 H82B 0.9800 . ? C82 H82C 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 C15 O10 H10 109.5 . . ? C16 C11 C12 121.2(14) . . ? C16 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? C11 C12 C13 116.7(14) . . ? C11 C12 H12 121.6 . . ? C13 C12 H12 121.6 . . ? C14 C13 C12 121.6(12) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C15 121.4(13) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? O10 C15 C14 124.8(12) . . ? O10 C15 C16 117.8(11) . . ? C14 C15 C16 117.2(13) . . ? C11 C16 C15 121.9(13) . . ? C11 C16 N41 120.6(12) . . ? C15 C16 N41 117.3(12) . . ? C22 N21 C26 122.4(12) . . ? C22 N21 H21 118.8 . . ? C26 N21 H21 118.8 . . ? N21 C22 C23 119.9(13) . . ? N21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? C22 C23 C24 118.2(13) . . ? C22 C23 H23 120.9 . . ? C24 C23 H23 120.9 . . ? C25 C24 C23 120.3(13) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C26 C25 C24 120.9(12) . . ? C26 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? C25 C26 N21 118.3(11) . . ? C25 C26 C71 127.0(11) . . ? N21 C26 C71 114.6(10) . . ? C32 N31 C36 122.8(12) . . ? C32 N31 H31 118.6 . . ? C36 N31 H31 118.6 . . ? N31 C32 C33 122.2(13) . . ? N31 C32 H32 118.9 . . ? C33 C32 H32 118.9 . . ? C34 C33 C32 115.9(13) . . ? C34 C33 H33 122.1 . . ? C32 C33 H33 122.1 . . ? C33 C34 C35 125.0(14) . . ? C33 C34 H34 117.5 . . ? C35 C34 H34 117.5 . . ? C34 C35 C36 117.5(13) . . ? C34 C35 H35 121.2 . . ? C36 C35 H35 121.2 . . ? N31 C36 C35 116.6(11) . . ? N31 C36 C61 117.7(12) . . ? C35 C36 C61 125.6(11) . . ? C42 N41 C45 108.4(9) . . ? C42 N41 C16 126.4(9) . . ? C45 N41 C16 125.2(11) . . ? N43 C42 N41 108.8(10) . . ? N43 C42 H42 125.6 . . ? N41 C42 H42 125.6 . . ? C42 N43 C44 108.8(10) . . ? C42 N43 H43 125.6 . . ? C44 N43 H43 125.6 . . ? C45 C44 N43 107.1(10) . . ? C45 C44 C51 132.0(11) . . ? N43 C44 C51 120.9(10) . . ? C44 C45 N41 106.9(10) . . ? C44 C45 H45 126.6 . . ? N41 C45 H45 126.6 . . ? C52 C51 C44 110.3(9) . . ? C52 C51 H51A 109.6 . . ? C44 C51 H51A 109.6 . . ? C52 C51 H51B 109.6 . . ? C44 C51 H51B 109.6 . . ? H51A C51 H51B 108.1 . . ? C51 C52 N53 113.5(8) . . ? C51 C52 H52A 108.9 . . ? N53 C52 H52A 108.9 . . ? C51 C52 H52B 108.9 . . ? N53 C52 H52B 108.9 . . ? H52A C52 H52B 107.7 . . ? C72 N53 C62 113.7(8) . . ? C72 N53 C52 112.9(7) . . ? C62 N53 C52 111.4(8) . . ? C72 N53 H53 106.1 . . ? C62 N53 H53 106.1 . . ? C52 N53 H53 106.1 . . ? N53 C62 C61 113.8(8) . . ? N53 C62 H62A 108.8 . . ? C61 C62 H62A 108.8 . . ? N53 C62 H62B 108.8 . . ? C61 C62 H62B 108.8 . . ? H62A C62 H62B 107.7 . . ? C36 C61 C62 110.4(9) . . ? C36 C61 H61A 109.6 . . ? C62 C61 H61A 109.6 . . ? C36 C61 H61B 109.6 . . ? C62 C61 H61B 109.6 . . ? H61A C61 H61B 108.1 . . ? C26 C71 C72 112.5(9) . . ? C26 C71 H71A 109.1 . . ? C72 C71 H71A 109.1 . . ? C26 C71 H71B 109.1 . . ? C72 C71 H71B 109.1 . . ? H71A C71 H71B 107.8 . . ? N53 C72 C71 112.6(8) . . ? N53 C72 H72A 109.1 . . ? C71 C72 H72A 109.1 . . ? N53 C72 H72B 109.1 . . ? C71 C72 H72B 109.1 . . ? H72A C72 H72B 107.8 . . ? O82 C81 H81A 109.5 . . ? O82 C81 H81B 109.5 . . ? H81A C81 H81B 109.5 . . ? O82 C81 H81C 109.5 . . ? H81A C81 H81C 109.5 . . ? H81B C81 H81C 109.5 . . ? C81 O82 H82 109.5 . . ? C82 O84 H84 109.5 . . ? O84 C82 H82A 109.5 . . ? O84 C82 H82B 109.5 . . ? H82A C82 H82B 109.5 . . ? O84 C82 H82C 109.5 . . ? H82A C82 H82C 109.5 . . ? H82B C82 H82C 109.5 . . ? loop_ _geom_hbond_atom_site_label_d _geom_hbond_atom_site_label_h _geom_hbond_distance_dh _geom_hbond_distance_ha _geom_hbond_angle_dha _geom_hbond_distance_da _geom_hbond_atom_site_label_a _geom_hbond_site_symmetry_a _geom_hbond_publ_flag O10 H10 0.840 1.819 168.91 2.65(1) O82 2_656 Y N21 H21 0.880 2.373 167.69 3.24(1) Br2 3_667 Y N31 H31 0.880 2.431 149.18 3.22(1) Br2 3_667 Y N43 H43 0.880 1.757 162.33 2.61(2) O84 1_555 Y N43 H43 0.880 1.933 159.82 2.78(2) O83 1_555 Y N53 H53 0.930 2.263 169.63 3.182(9) Br1 1_565 Y O82 H82 0.840 2.353 159.37 3.153(9) Br4 1_545 Y O84 H84 0.840 2.552 150.46 3.31(1) Br3 1_655 Y _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.240 _refine_diff_density_min -0.987 _refine_diff_density_rms 0.192