# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email mshi@mail.sioc.ac.cn _publ_contact_author_name 'Min Shi' _publ_author_name 'Min Shi' data_cd201373 _database_code_depnum_ccdc_archive 'CCDC 783732' #TrackingRef 'cd201373.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 Br F2 N O2' _chemical_formula_weight 422.26 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' F F 0.0171 0.0103 '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.2224(14) _cell_length_b 10.4748(16) _cell_length_c 10.2384(16) _cell_angle_alpha 90.00 _cell_angle_beta 104.482(3) _cell_angle_gamma 90.00 _cell_volume 957.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1431 _cell_measurement_theta_min 4.562 _cell_measurement_theta_max 38.950 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.485 _exptl_crystal_size_mid 0.451 _exptl_crystal_size_min 0.397 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.464 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 2.178 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.1181 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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_% ? _diffrn_reflns_number 5612 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_sigmaI/netI 0.0855 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3850 _reflns_number_gt 1787 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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 [0.00000+1.00000exp(2.00(sin\q/\l)^2^)]/ [\s^2^(Fo^2^)+0.0000+0.0000*P+(0.0463P)^2^+0.0000sin\q/\l] where P = 0.33333Fo^2^ + 0.66667Fc^2^ ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0185(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.079(10) _chemical_absolute_configuration ad _refine_ls_number_reflns 3850 _refine_ls_number_parameters 241 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0920 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1005 _refine_ls_wR_factor_gt 0.0880 _refine_ls_goodness_of_fit_ref 0.887 _refine_ls_restrained_S_all 0.887 _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 Br Br 1.45695(6) 0.68877(8) 0.98916(6) 0.1147(3) Uani 1 1 d . . . F1 F 0.8816(3) 0.7582(3) 0.4378(3) 0.0900(9) Uani 1 1 d . . . F2 F 0.9529(3) 0.5689(3) 0.3978(3) 0.0837(8) Uani 1 1 d . . . O1 O 0.3513(5) 0.3971(4) 0.4245(4) 0.0984(12) Uani 1 1 d . . . O2 O 0.5194(3) 0.5531(3) 0.4745(3) 0.0663(8) Uani 1 1 d . . . N1 N 0.8160(4) 0.4571(3) 0.5824(3) 0.0501(8) Uani 1 1 d D . . C1 C 0.4504(6) 0.4536(6) 0.3955(5) 0.0703(13) Uani 1 1 d . . . C2 C 0.5240(7) 0.4370(6) 0.2878(5) 0.0862(16) Uani 1 1 d . . . H2 H 0.4985 0.3764 0.2196 0.103 Uiso 1 1 calc R . . C3 C 0.6320(6) 0.5205(7) 0.3010(5) 0.0902(18) Uani 1 1 d . . . H3 H 0.6943 0.5294 0.2428 0.108 Uiso 1 1 calc R . . C4 C 0.6398(5) 0.5982(4) 0.4222(5) 0.0675(13) Uani 1 1 d . . . H4 H 0.6230 0.6881 0.3964 0.081 Uiso 1 1 calc R . . C5 C 0.7848(4) 0.5858(4) 0.5357(4) 0.0518(10) Uani 1 1 d . . . H5 H 0.7702 0.6358 0.6123 0.062 Uiso 1 1 calc R . . C6 C 0.9204(6) 0.6408(4) 0.4975(4) 0.0634(13) Uani 1 1 d . . . C7 C 1.0551(5) 0.6557(4) 0.6125(4) 0.0574(12) Uani 1 1 d . . . C8 C 1.0498(5) 0.7384(4) 0.7154(5) 0.0704(13) Uani 1 1 d . . . H8 H 0.9658 0.7893 0.7095 0.084 Uiso 1 1 calc R . . C9 C 1.1698(6) 0.7460(5) 0.8282(5) 0.0796(14) Uani 1 1 d . . . H9 H 1.1642 0.7991 0.8995 0.095 Uiso 1 1 calc R . . C10 C 1.2943(5) 0.6769(6) 0.8347(5) 0.0734(12) Uani 1 1 d . . . C11 C 1.3036(5) 0.5968(5) 0.7325(6) 0.0784(14) Uani 1 1 d . . . H11 H 1.3906 0.5500 0.7375 0.094 Uiso 1 1 calc R . . C12 C 1.1835(6) 0.5852(5) 0.6214(5) 0.0727(13) Uani 1 1 d . . . H12 H 1.1891 0.5295 0.5521 0.087 Uiso 1 1 calc R . . C13 C 0.7654(5) 0.4167(4) 0.6992(4) 0.0550(11) Uani 1 1 d . . . H13 H 0.6702 0.4592 0.6969 0.066 Uiso 1 1 calc R . . C14 C 0.7385(6) 0.2715(4) 0.6886(5) 0.0783(14) Uani 1 1 d . . . H14A H 0.6649 0.2524 0.6065 0.117 Uiso 1 1 calc R . . H14B H 0.7033 0.2428 0.7643 0.117 Uiso 1 1 calc R . . H14C H 0.8306 0.2288 0.6885 0.117 Uiso 1 1 calc R . . C15 C 0.8766(5) 0.4518(4) 0.8287(4) 0.0545(11) Uani 1 1 d . . . C16 C 0.8357(7) 0.5284(5) 0.9238(5) 0.0858(15) Uani 1 1 d . . . H16 H 0.7400 0.5632 0.9062 0.103 Uiso 1 1 calc R . . C17 C 0.9396(11) 0.5532(6) 1.0468(6) 0.105(2) Uani 1 1 d . . . H17 H 0.9126 0.6037 1.1116 0.126 Uiso 1 1 calc R . . C18 C 1.0785(11) 0.5037(7) 1.0710(7) 0.108(2) Uani 1 1 d . . . H18 H 1.1466 0.5210 1.1527 0.130 Uiso 1 1 calc R . . C19 C 1.1209(7) 0.4299(7) 0.9796(6) 0.0917(17) Uani 1 1 d . . . H19 H 1.2172 0.3962 0.9980 0.110 Uiso 1 1 calc R . . C20 C 1.0195(6) 0.4048(4) 0.8582(5) 0.0676(13) Uani 1 1 d . . . H20 H 1.0493 0.3545 0.7947 0.081 Uiso 1 1 calc R . . H1 H 0.814(5) 0.407(4) 0.515(3) 0.084(17) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br 0.0881(4) 0.1653(7) 0.0842(4) 0.0109(5) 0.0090(3) 0.0035(5) F1 0.095(2) 0.079(2) 0.098(2) 0.0422(16) 0.0290(18) 0.0000(16) F2 0.0805(18) 0.114(2) 0.0661(16) -0.0105(16) 0.0363(14) -0.0050(17) O1 0.083(3) 0.098(3) 0.116(3) -0.014(2) 0.029(2) -0.012(2) O2 0.0557(18) 0.073(2) 0.071(2) 0.0088(17) 0.0172(16) 0.0143(16) N1 0.062(2) 0.050(2) 0.0406(19) 0.0042(18) 0.0167(17) 0.0080(17) C1 0.057(3) 0.080(4) 0.067(3) -0.002(3) 0.002(3) 0.012(3) C2 0.068(4) 0.122(5) 0.060(3) -0.015(3) 0.001(3) 0.022(3) C3 0.061(3) 0.166(6) 0.041(3) 0.013(3) 0.008(2) 0.020(4) C4 0.063(3) 0.068(3) 0.072(3) 0.026(3) 0.019(2) 0.014(2) C5 0.056(2) 0.051(3) 0.052(2) 0.0096(19) 0.018(2) 0.011(2) C6 0.082(4) 0.057(3) 0.060(3) 0.013(2) 0.034(3) 0.013(2) C7 0.060(3) 0.061(3) 0.059(3) 0.006(2) 0.029(2) 0.002(2) C8 0.058(3) 0.069(3) 0.088(3) -0.001(3) 0.026(3) 0.009(2) C9 0.078(4) 0.080(4) 0.085(4) -0.011(3) 0.029(3) -0.002(3) C10 0.067(3) 0.083(3) 0.077(3) 0.002(3) 0.031(2) -0.002(3) C11 0.060(3) 0.090(4) 0.089(4) 0.014(3) 0.025(3) 0.016(3) C12 0.075(3) 0.081(3) 0.072(3) -0.014(3) 0.037(3) 0.007(3) C13 0.050(3) 0.064(3) 0.055(3) 0.012(2) 0.022(2) 0.008(2) C14 0.087(3) 0.069(3) 0.069(3) 0.013(2) 0.002(2) -0.031(3) C15 0.072(3) 0.048(2) 0.046(2) 0.002(2) 0.019(2) -0.002(2) C16 0.117(4) 0.077(4) 0.074(4) 0.006(3) 0.044(3) 0.006(3) C17 0.182(7) 0.081(4) 0.068(4) -0.031(3) 0.061(5) -0.041(5) C18 0.146(7) 0.107(6) 0.066(4) -0.008(4) 0.015(4) -0.059(5) C19 0.092(4) 0.097(4) 0.074(4) 0.003(3) -0.003(3) -0.018(3) C20 0.074(4) 0.062(3) 0.057(3) -0.002(2) -0.001(3) 0.003(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 Br C10 1.892(5) . ? F1 C6 1.379(5) . ? F2 C6 1.361(5) . ? O1 C1 1.187(6) . ? O2 C1 1.374(6) . ? O2 C4 1.428(5) . ? N1 C5 1.436(5) . ? N1 C13 1.450(5) . ? N1 H1 0.858(19) . ? C1 C2 1.442(7) . ? C2 C3 1.307(8) . ? C2 H2 0.9300 . ? C3 C4 1.470(7) . ? C3 H3 0.9300 . ? C4 C5 1.542(6) . ? C4 H4 0.9800 . ? C5 C6 1.514(6) . ? C5 H5 0.9800 . ? C6 C7 1.491(6) . ? C7 C8 1.374(6) . ? C7 C12 1.379(6) . ? C8 C9 1.387(7) . ? C8 H8 0.9300 . ? C9 C10 1.344(6) . ? C9 H9 0.9300 . ? C10 C11 1.360(7) . ? C11 C12 1.381(7) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C15 1.505(6) . ? C13 C14 1.541(6) . ? C13 H13 0.9800 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C20 1.368(6) . ? C15 C16 1.385(6) . ? C16 C17 1.403(9) . ? C16 H16 0.9300 . ? C17 C18 1.346(9) . ? C17 H17 0.9300 . ? C18 C19 1.345(9) . ? C18 H18 0.9300 . ? C19 C20 1.381(7) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? 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 O2 C4 108.6(4) . . ? C5 N1 C13 118.0(3) . . ? C5 N1 H1 110(3) . . ? C13 N1 H1 122(3) . . ? O1 C1 O2 120.2(5) . . ? O1 C1 C2 132.1(6) . . ? O2 C1 C2 107.7(5) . . ? C3 C2 C1 109.4(5) . . ? C3 C2 H2 125.3 . . ? C1 C2 H2 125.3 . . ? C2 C3 C4 109.5(5) . . ? C2 C3 H3 125.3 . . ? C4 C3 H3 125.3 . . ? O2 C4 C3 104.7(4) . . ? O2 C4 C5 107.4(3) . . ? C3 C4 C5 116.1(4) . . ? O2 C4 H4 109.5 . . ? C3 C4 H4 109.5 . . ? C5 C4 H4 109.5 . . ? N1 C5 C6 109.5(3) . . ? N1 C5 C4 113.2(3) . . ? C6 C5 C4 112.9(3) . . ? N1 C5 H5 106.9 . . ? C6 C5 H5 106.9 . . ? C4 C5 H5 106.9 . . ? F2 C6 F1 104.0(3) . . ? F2 C6 C7 110.7(4) . . ? F1 C6 C7 109.3(4) . . ? F2 C6 C5 109.5(4) . . ? F1 C6 C5 108.3(4) . . ? C7 C6 C5 114.5(3) . . ? C8 C7 C12 118.8(4) . . ? C8 C7 C6 119.3(4) . . ? C12 C7 C6 121.9(4) . . ? C7 C8 C9 120.0(4) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 120.3(5) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 120.8(4) . . ? C9 C10 Br 119.7(4) . . ? C11 C10 Br 119.6(4) . . ? C10 C11 C12 119.7(4) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C7 C12 C11 120.4(5) . . ? C7 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? N1 C13 C15 111.5(3) . . ? N1 C13 C14 108.0(3) . . ? C15 C13 C14 111.4(3) . . ? N1 C13 H13 108.6 . . ? C15 C13 H13 108.6 . . ? C14 C13 H13 108.6 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C20 C15 C16 118.0(4) . . ? C20 C15 C13 120.9(4) . . ? C16 C15 C13 121.0(4) . . ? C15 C16 C17 119.6(6) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C18 C17 C16 119.9(6) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C19 C18 C17 121.5(6) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C18 C19 C20 119.1(6) . . ? C18 C19 H19 120.5 . . ? C20 C19 H19 120.5 . . ? C15 C20 C19 121.9(5) . . ? C15 C20 H20 119.0 . . ? C19 C20 H20 119.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 O2 C1 O1 176.2(5) . . . . ? C4 O2 C1 C2 -2.0(5) . . . . ? O1 C1 C2 C3 -177.4(6) . . . . ? O2 C1 C2 C3 0.5(6) . . . . ? C1 C2 C3 C4 1.1(6) . . . . ? C1 O2 C4 C3 2.6(4) . . . . ? C1 O2 C4 C5 -121.4(4) . . . . ? C2 C3 C4 O2 -2.3(5) . . . . ? C2 C3 C4 C5 115.9(5) . . . . ? C13 N1 C5 C6 138.5(4) . . . . ? C13 N1 C5 C4 -94.5(4) . . . . ? O2 C4 C5 N1 59.6(4) . . . . ? C3 C4 C5 N1 -57.1(5) . . . . ? O2 C4 C5 C6 -175.2(3) . . . . ? C3 C4 C5 C6 68.1(5) . . . . ? N1 C5 C6 F2 60.0(5) . . . . ? C4 C5 C6 F2 -67.2(4) . . . . ? N1 C5 C6 F1 172.8(3) . . . . ? C4 C5 C6 F1 45.6(5) . . . . ? N1 C5 C6 C7 -65.0(5) . . . . ? C4 C5 C6 C7 167.8(4) . . . . ? F2 C6 C7 C8 171.8(4) . . . . ? F1 C6 C7 C8 57.9(5) . . . . ? C5 C6 C7 C8 -63.8(5) . . . . ? F2 C6 C7 C12 -10.6(6) . . . . ? F1 C6 C7 C12 -124.6(4) . . . . ? C5 C6 C7 C12 113.7(5) . . . . ? C12 C7 C8 C9 -2.7(6) . . . . ? C6 C7 C8 C9 174.9(4) . . . . ? C7 C8 C9 C10 3.0(7) . . . . ? C8 C9 C10 C11 -1.3(8) . . . . ? C8 C9 C10 Br 179.9(4) . . . . ? C9 C10 C11 C12 -0.7(8) . . . . ? Br C10 C11 C12 178.2(4) . . . . ? C8 C7 C12 C11 0.7(7) . . . . ? C6 C7 C12 C11 -176.8(4) . . . . ? C10 C11 C12 C7 0.9(8) . . . . ? C5 N1 C13 C15 -85.0(5) . . . . ? C5 N1 C13 C14 152.3(4) . . . . ? N1 C13 C15 C20 -60.6(5) . . . . ? C14 C13 C15 C20 60.1(5) . . . . ? N1 C13 C15 C16 121.9(4) . . . . ? C14 C13 C15 C16 -117.3(5) . . . . ? C20 C15 C16 C17 -1.2(7) . . . . ? C13 C15 C16 C17 176.3(4) . . . . ? C15 C16 C17 C18 0.7(8) . . . . ? C16 C17 C18 C19 -0.2(10) . . . . ? C17 C18 C19 C20 0.2(9) . . . . ? C16 C15 C20 C19 1.2(7) . . . . ? C13 C15 C20 C19 -176.3(5) . . . . ? C18 C19 C20 C15 -0.7(8) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.294 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.042 data_cd201634 _database_code_depnum_ccdc_archive 'CCDC 805801' #TrackingRef 'cd201634.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 N2 O6' _chemical_formula_weight 330.29 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 14.2927(11) _cell_length_b 6.5471(5) _cell_length_c 16.4441(14) _cell_angle_alpha 90.00 _cell_angle_beta 93.366(2) _cell_angle_gamma 90.00 _cell_volume 1536.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2734 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 26.80 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.609402 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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_% ? _diffrn_reflns_number 7746 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2853 _reflns_number_gt 2219 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1149P)^2^+0.2658P] 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 2853 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0653 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1751 _refine_ls_wR_factor_gt 0.1648 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _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 N1 N 0.75462(10) -0.0673(2) 0.37207(10) 0.0351(4) Uani 1 1 d . . . N2 N 0.76901(15) 0.2214(3) 0.50799(12) 0.0520(5) Uani 1 1 d . . . O1 O 0.77976(11) -0.3499(2) 0.45150(12) 0.0656(5) Uani 1 1 d . . . O2 O 0.69757(10) 0.1709(2) 0.28061(10) 0.0533(4) Uani 1 1 d . . . O3 O 0.47144(15) 0.1706(4) 0.24775(18) 0.1173(10) Uani 1 1 d . . . O4 O 0.40272(14) 0.1628(3) 0.36562(16) 0.0961(8) Uani 1 1 d . . . O5 O 0.78557(16) 0.2707(4) 0.57812(12) 0.0876(7) Uani 1 1 d . . . O6 O 0.68969(12) 0.2127(3) 0.47527(12) 0.0689(5) Uani 1 1 d . . . C1 C 0.68884(12) 0.0104(3) 0.31499(12) 0.0371(5) Uani 1 1 d . . . C2 C 0.60919(13) -0.1409(3) 0.30623(13) 0.0409(5) Uani 1 1 d . . . H2 H 0.5957 -0.1792 0.2491 0.049 Uiso 1 1 calc R . . C3 C 0.52158(13) -0.0722(3) 0.34556(14) 0.0466(5) Uani 1 1 d . . . C4 C 0.50005(15) -0.1944(4) 0.40566(16) 0.0561(6) Uani 1 1 d . . . H4 H 0.4488 -0.1735 0.4370 0.067 Uiso 1 1 calc R . . C5 C 0.56603(16) -0.3689(4) 0.41807(18) 0.0600(7) Uani 1 1 d . . . H5A H 0.5348 -0.4977 0.4058 0.072 Uiso 1 1 calc R . . H5B H 0.5927 -0.3724 0.4737 0.072 Uiso 1 1 calc R . . C6 C 0.64197(14) -0.3262(3) 0.35794(13) 0.0422(5) Uani 1 1 d . . . H6A H 0.6515 -0.4455 0.3234 0.051 Uiso 1 1 calc R . . C7 C 0.73283(13) -0.2595(3) 0.40053(13) 0.0407(5) Uani 1 1 d . . . C8 C 0.46447(16) 0.0995(4) 0.3137(2) 0.0663(8) Uani 1 1 d . . . C9 C 0.3370(2) 0.3217(6) 0.3384(4) 0.1241(17) Uani 1 1 d . . . H9A H 0.3366 0.4277 0.3795 0.149 Uiso 1 1 calc R . . H9B H 0.3580 0.3827 0.2889 0.149 Uiso 1 1 calc R . . C10 C 0.2482(2) 0.2500(6) 0.3238(3) 0.1209(16) Uani 1 1 d . . . H10A H 0.2459 0.1627 0.2768 0.181 Uiso 1 1 calc R . . H10B H 0.2060 0.3627 0.3141 0.181 Uiso 1 1 calc R . . H10C H 0.2299 0.1740 0.3702 0.181 Uiso 1 1 calc R . . C11 C 0.84027(12) 0.0339(3) 0.39583(12) 0.0355(5) Uani 1 1 d . . . C12 C 0.84854(14) 0.1725(3) 0.45953(13) 0.0410(5) Uani 1 1 d . . . C13 C 0.93379(16) 0.2628(3) 0.48089(16) 0.0537(6) Uani 1 1 d . . . H13 H 0.9393 0.3541 0.5242 0.064 Uiso 1 1 calc R . . C14 C 1.01045(16) 0.2168(4) 0.43760(17) 0.0578(7) Uani 1 1 d . . . H14 H 1.0674 0.2813 0.4503 0.069 Uiso 1 1 calc R . . C15 C 1.00334(14) 0.0767(4) 0.37598(16) 0.0531(6) Uani 1 1 d . . . H15 H 1.0560 0.0433 0.3481 0.064 Uiso 1 1 calc R . . C16 C 0.91855(13) -0.0155(3) 0.35492(13) 0.0435(5) Uani 1 1 d . . . H16 H 0.9142 -0.1111 0.3130 0.052 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 0.0284(8) 0.0356(8) 0.0413(9) 0.0016(7) 0.0018(6) -0.0015(6) N2 0.0607(13) 0.0396(10) 0.0567(13) -0.0040(9) 0.0120(10) 0.0011(9) O1 0.0524(10) 0.0531(10) 0.0886(13) 0.0291(9) -0.0192(9) -0.0099(7) O2 0.0402(9) 0.0562(9) 0.0631(10) 0.0234(8) -0.0012(7) -0.0039(7) O3 0.0631(14) 0.139(2) 0.152(2) 0.090(2) 0.0224(14) 0.0276(13) O4 0.0592(12) 0.0848(15) 0.147(2) 0.0302(14) 0.0311(13) 0.0349(10) O5 0.1116(18) 0.0963(16) 0.0553(12) -0.0187(11) 0.0075(11) 0.0170(13) O6 0.0481(11) 0.0736(12) 0.0873(13) -0.0194(10) 0.0229(9) -0.0037(8) C1 0.0295(10) 0.0439(11) 0.0383(10) 0.0034(9) 0.0059(8) 0.0017(8) C2 0.0321(10) 0.0469(11) 0.0434(11) -0.0015(9) 0.0003(8) -0.0042(8) C3 0.0277(10) 0.0500(12) 0.0623(14) 0.0055(10) 0.0039(9) -0.0031(9) C4 0.0351(11) 0.0614(14) 0.0731(16) 0.0088(12) 0.0149(11) -0.0025(10) C5 0.0402(12) 0.0581(14) 0.0822(17) 0.0215(13) 0.0098(11) -0.0042(10) C6 0.0339(10) 0.0370(10) 0.0557(13) -0.0034(9) 0.0024(9) -0.0035(8) C7 0.0336(10) 0.0367(10) 0.0519(12) 0.0040(9) 0.0028(9) -0.0014(8) C8 0.0300(12) 0.0645(15) 0.105(2) 0.0299(16) 0.0066(13) -0.0018(11) C9 0.0551(19) 0.087(2) 0.231(5) 0.043(3) 0.020(2) 0.0324(17) C10 0.064(2) 0.085(2) 0.209(5) 0.014(3) -0.033(3) 0.0009(18) C11 0.0297(9) 0.0331(9) 0.0434(11) 0.0053(8) -0.0004(8) -0.0018(7) C12 0.0404(11) 0.0318(10) 0.0506(12) 0.0043(9) 0.0011(9) 0.0014(8) C13 0.0547(14) 0.0354(11) 0.0693(16) -0.0036(11) -0.0107(12) -0.0056(10) C14 0.0351(12) 0.0454(12) 0.0910(19) 0.0080(12) -0.0117(12) -0.0089(9) C15 0.0317(11) 0.0558(13) 0.0717(15) 0.0081(12) 0.0031(10) -0.0007(9) C16 0.0334(10) 0.0479(12) 0.0494(12) 0.0015(9) 0.0028(9) 0.0014(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C7 1.384(3) . ? N1 C1 1.386(2) . ? N1 C11 1.426(2) . ? N2 O5 1.207(3) . ? N2 O6 1.227(3) . ? N2 C12 1.462(3) . ? O1 C7 1.198(2) . ? O2 C1 1.203(2) . ? O3 C8 1.189(3) . ? O4 C8 1.330(4) . ? O4 C9 1.455(4) . ? C1 C2 1.510(3) . ? C2 C3 1.511(3) . ? C2 C6 1.539(3) . ? C2 H2 0.9800 . ? C3 C4 1.322(3) . ? C3 C8 1.468(3) . ? C4 C5 1.487(3) . ? C4 H4 0.9300 . ? C5 C6 1.536(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.504(3) . ? C6 H6A 0.9800 . ? C9 C10 1.362(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C16 1.377(3) . ? C11 C12 1.386(3) . ? C12 C13 1.381(3) . ? C13 C14 1.375(4) . ? C13 H13 0.9300 . ? C14 C15 1.366(4) . ? C14 H14 0.9300 . ? C15 C16 1.380(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? 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 C7 N1 C1 113.94(15) . . ? C7 N1 C11 122.43(15) . . ? C1 N1 C11 123.51(15) . . ? O5 N2 O6 123.7(2) . . ? O5 N2 C12 117.7(2) . . ? O6 N2 C12 118.6(2) . . ? C8 O4 C9 117.8(3) . . ? O2 C1 N1 123.66(17) . . ? O2 C1 C2 128.81(18) . . ? N1 C1 C2 107.53(16) . . ? C1 C2 C3 113.77(17) . . ? C1 C2 C6 105.15(15) . . ? C3 C2 C6 103.37(17) . . ? C1 C2 H2 111.4 . . ? C3 C2 H2 111.4 . . ? C6 C2 H2 111.4 . . ? C4 C3 C8 125.6(2) . . ? C4 C3 C2 112.03(19) . . ? C8 C3 C2 122.2(2) . . ? C3 C4 C5 113.2(2) . . ? C3 C4 H4 123.4 . . ? C5 C4 H4 123.4 . . ? C4 C5 C6 103.80(19) . . ? C4 C5 H5A 111.0 . . ? C6 C5 H5A 111.0 . . ? C4 C5 H5B 111.0 . . ? C6 C5 H5B 111.0 . . ? H5A C5 H5B 109.0 . . ? C7 C6 C5 112.12(19) . . ? C7 C6 C2 104.78(16) . . ? C5 C6 C2 107.17(17) . . ? C7 C6 H6A 110.9 . . ? C5 C6 H6A 110.9 . . ? C2 C6 H6A 110.9 . . ? O1 C7 N1 123.87(18) . . ? O1 C7 C6 127.95(19) . . ? N1 C7 C6 108.17(16) . . ? O3 C8 O4 123.9(2) . . ? O3 C8 C3 123.4(3) . . ? O4 C8 C3 112.7(2) . . ? C10 C9 O4 112.7(3) . . ? C10 C9 H9A 109.0 . . ? O4 C9 H9A 109.0 . . ? C10 C9 H9B 109.0 . . ? O4 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 119.15(18) . . ? C16 C11 N1 117.77(18) . . ? C12 C11 N1 123.03(17) . . ? C13 C12 C11 120.5(2) . . ? C13 C12 N2 118.0(2) . . ? C11 C12 N2 121.41(18) . . ? C14 C13 C12 119.5(2) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C15 C14 C13 120.3(2) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 120.4(2) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C11 C16 C15 120.1(2) . . ? C11 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? 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 C7 N1 C1 O2 -176.52(19) . . . . ? C11 N1 C1 O2 -0.5(3) . . . . ? C7 N1 C1 C2 3.5(2) . . . . ? C11 N1 C1 C2 179.53(17) . . . . ? O2 C1 C2 C3 -73.7(3) . . . . ? N1 C1 C2 C3 106.26(18) . . . . ? O2 C1 C2 C6 173.9(2) . . . . ? N1 C1 C2 C6 -6.1(2) . . . . ? C1 C2 C3 C4 -116.8(2) . . . . ? C6 C2 C3 C4 -3.3(2) . . . . ? C1 C2 C3 C8 68.6(3) . . . . ? C6 C2 C3 C8 -178.0(2) . . . . ? C8 C3 C4 C5 173.4(2) . . . . ? C2 C3 C4 C5 -1.0(3) . . . . ? C3 C4 C5 C6 4.9(3) . . . . ? C4 C5 C6 C7 107.8(2) . . . . ? C4 C5 C6 C2 -6.7(2) . . . . ? C1 C2 C6 C7 6.4(2) . . . . ? C3 C2 C6 C7 -113.16(18) . . . . ? C1 C2 C6 C5 125.69(19) . . . . ? C3 C2 C6 C5 6.1(2) . . . . ? C1 N1 C7 O1 -178.1(2) . . . . ? C11 N1 C7 O1 5.9(3) . . . . ? C1 N1 C7 C6 0.8(2) . . . . ? C11 N1 C7 C6 -175.27(17) . . . . ? C5 C6 C7 O1 58.3(3) . . . . ? C2 C6 C7 O1 174.2(2) . . . . ? C5 C6 C7 N1 -120.50(19) . . . . ? C2 C6 C7 N1 -4.6(2) . . . . ? C9 O4 C8 O3 3.1(5) . . . . ? C9 O4 C8 C3 -175.2(3) . . . . ? C4 C3 C8 O3 -159.0(3) . . . . ? C2 C3 C8 O3 14.9(4) . . . . ? C4 C3 C8 O4 19.4(4) . . . . ? C2 C3 C8 O4 -166.7(2) . . . . ? C8 O4 C9 C10 107.6(5) . . . . ? C7 N1 C11 C16 82.9(2) . . . . ? C1 N1 C11 C16 -92.8(2) . . . . ? C7 N1 C11 C12 -94.7(2) . . . . ? C1 N1 C11 C12 89.6(2) . . . . ? C16 C11 C12 C13 1.1(3) . . . . ? N1 C11 C12 C13 178.70(18) . . . . ? C16 C11 C12 N2 -176.43(18) . . . . ? N1 C11 C12 N2 1.1(3) . . . . ? O5 N2 C12 C13 -27.1(3) . . . . ? O6 N2 C12 C13 152.1(2) . . . . ? O5 N2 C12 C11 150.6(2) . . . . ? O6 N2 C12 C11 -30.3(3) . . . . ? C11 C12 C13 C14 1.0(3) . . . . ? N2 C12 C13 C14 178.7(2) . . . . ? C12 C13 C14 C15 -2.6(4) . . . . ? C13 C14 C15 C16 2.0(4) . . . . ? C12 C11 C16 C15 -1.8(3) . . . . ? N1 C11 C16 C15 -179.45(18) . . . . ? C14 C15 C16 C11 0.2(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.320 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.046 data_cd211381 _database_code_depnum_ccdc_archive 'CCDC 844461' #TrackingRef 'cd211381.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H25 Br N2 O3' _chemical_formula_weight 433.34 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)/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 8.960(7) _cell_length_b 21.905(17) _cell_length_c 20.488(16) _cell_angle_alpha 90.00 _cell_angle_beta 98.968(17) _cell_angle_gamma 90.00 _cell_volume 3972(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2095 _cell_measurement_theta_min 4.960 _cell_measurement_theta_max 43.149 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.265 _exptl_crystal_size_mid 0.071 _exptl_crystal_size_min 0.063 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1792 _exptl_absorpt_coefficient_mu 2.093 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2635 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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_% ? _diffrn_reflns_number 16455 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_sigmaI/netI 0.0789 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.50 _reflns_number_total 7349 _reflns_number_gt 3819 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0899P)^2^+0.6925P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7349 _refine_ls_number_parameters 495 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1320 _refine_ls_R_factor_gt 0.0646 _refine_ls_wR_factor_ref 0.1916 _refine_ls_wR_factor_gt 0.1571 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 Br1 Br 0.35016(9) 0.28722(4) 0.43181(4) 0.1016(3) Uani 1 1 d . . . Br2 Br -0.09345(11) 0.76762(4) 0.45661(4) 0.1073(4) Uani 1 1 d . . . N1 N 0.6899(5) 0.1569(2) 0.30032(19) 0.0443(11) Uani 1 1 d . . . N2 N 0.3711(4) 0.05035(19) 0.1189(2) 0.0498(11) Uani 1 1 d . . . N3 N -0.1774(5) 0.6659(2) 0.2290(2) 0.0522(12) Uani 1 1 d . . . N4 N 0.0453(4) 0.48746(18) 0.1371(2) 0.0457(10) Uani 1 1 d . . . O1 O 0.4711(3) 0.17484(17) 0.23119(16) 0.0570(10) Uani 1 1 d . . . O2 O 0.4298(4) 0.04097(19) 0.22981(18) 0.0681(11) Uani 1 1 d . . . O3 O 0.3795(4) 0.06083(19) 0.01002(18) 0.0741(12) Uani 1 1 d . . . O4 O -0.0158(4) 0.64755(19) 0.1581(2) 0.0750(12) Uani 1 1 d . . . O5 O 0.0675(4) 0.5376(2) 0.2346(2) 0.0817(14) Uani 1 1 d . . . O6 O -0.0440(4) 0.44080(19) 0.0407(2) 0.0714(11) Uani 1 1 d . . . C1 C 0.6033(5) 0.1567(2) 0.2407(2) 0.0444(12) Uani 1 1 d . . . C2 C 0.6763(5) 0.1322(2) 0.1861(2) 0.0438(12) Uani 1 1 d . . . H2 H 0.7861 0.1321 0.1998 0.053 Uiso 1 1 calc R . . C3 C 0.6378(6) 0.1700(3) 0.1232(2) 0.0561(14) Uani 1 1 d . . . H3A H 0.5321 0.1817 0.1159 0.067 Uiso 1 1 calc R . . H3B H 0.6997 0.2065 0.1251 0.067 Uiso 1 1 calc R . . C4 C 0.6721(6) 0.1278(3) 0.0702(2) 0.0595(15) Uani 1 1 d . . . H4A H 0.7799 0.1259 0.0692 0.071 Uiso 1 1 calc R . . H4B H 0.6209 0.1406 0.0271 0.071 Uiso 1 1 calc R . . C5 C 0.6121(5) 0.0662(2) 0.0900(2) 0.0504(13) Uani 1 1 d . . . H5 H 0.6695 0.0322 0.0751 0.061 Uiso 1 1 calc R . . C6 C 0.6241(5) 0.0671(2) 0.1647(2) 0.0415(12) Uani 1 1 d . . . H6 H 0.6977 0.0368 0.1848 0.050 Uiso 1 1 calc R . . C7 C 0.4687(5) 0.0513(2) 0.1776(2) 0.0461(12) Uani 1 1 d . . . C8 C 0.4438(6) 0.0594(2) 0.0655(3) 0.0523(13) Uani 1 1 d . . . C9 C 0.2089(5) 0.0388(3) 0.1141(3) 0.0592(15) Uani 1 1 d . . . H9A H 0.1589 0.0541 0.0718 0.071 Uiso 1 1 calc R . . H9B H 0.1710 0.0620 0.1484 0.071 Uiso 1 1 calc R . . C10 C 0.1661(6) -0.0258(3) 0.1201(4) 0.079(2) Uani 1 1 d . . . H10 H 0.1972 -0.0349 0.1671 0.095 Uiso 1 1 calc R . . C11 C -0.0066(6) -0.0324(3) 0.1099(4) 0.085(2) Uani 1 1 d . . . H11A H -0.0478 -0.0213 0.0649 0.103 Uiso 1 1 calc R . . H11B H -0.0480 -0.0047 0.1394 0.103 Uiso 1 1 calc R . . C12 C -0.0542(9) -0.0983(5) 0.1234(5) 0.143(4) Uani 1 1 d . . . H12A H -0.0253 -0.1074 0.1699 0.171 Uiso 1 1 calc R . . H12B H -0.1632 -0.1017 0.1128 0.171 Uiso 1 1 calc R . . C13 C 0.0123(9) -0.1407(4) 0.0862(5) 0.124(3) Uani 1 1 d . . . H13A H -0.0233 -0.1336 0.0397 0.149 Uiso 1 1 calc R . . H13B H -0.0188 -0.1814 0.0969 0.149 Uiso 1 1 calc R . . C14 C 0.1855(8) -0.1370(3) 0.0990(4) 0.091(2) Uani 1 1 d . . . H14A H 0.2273 -0.1640 0.0689 0.109 Uiso 1 1 calc R . . H14B H 0.2233 -0.1497 0.1438 0.109 Uiso 1 1 calc R . . C15 C 0.2340(8) -0.0707(4) 0.0883(5) 0.120(3) Uani 1 1 d . . . H15A H 0.3423 -0.0679 0.1024 0.144 Uiso 1 1 calc R . . H15B H 0.2148 -0.0622 0.0413 0.144 Uiso 1 1 calc R . . C16 C 0.6472(5) 0.1737(2) 0.3599(2) 0.0414(12) Uani 1 1 d . . . C17 C 0.7260(6) 0.1470(3) 0.4170(3) 0.0568(14) Uani 1 1 d . . . H17 H 0.8017 0.1185 0.4142 0.068 Uiso 1 1 calc R . . C18 C 0.6909(6) 0.1630(3) 0.4762(3) 0.0671(17) Uani 1 1 d . . . H18 H 0.7443 0.1457 0.5143 0.080 Uiso 1 1 calc R . . C19 C 0.5777(6) 0.2044(3) 0.4817(3) 0.0619(15) Uani 1 1 d . . . H19 H 0.5530 0.2144 0.5228 0.074 Uiso 1 1 calc R . . C20 C 0.5031(6) 0.2301(2) 0.4255(3) 0.0516(13) Uani 1 1 d . . . C21 C 0.5346(5) 0.2149(2) 0.3649(2) 0.0441(12) Uani 1 1 d . . . H21 H 0.4802 0.2323 0.3271 0.053 Uiso 1 1 calc R . . C22 C -0.1340(5) 0.6370(3) 0.1781(3) 0.0536(14) Uani 1 1 d . . . C23 C -0.2377(5) 0.5865(2) 0.1481(2) 0.0463(12) Uani 1 1 d . . . H23 H -0.3372 0.5923 0.1615 0.056 Uiso 1 1 calc R . . C24 C -0.2571(6) 0.5843(3) 0.0732(3) 0.0600(15) Uani 1 1 d . . . H24A H -0.3295 0.6147 0.0537 0.072 Uiso 1 1 calc R . . H24B H -0.1616 0.5913 0.0577 0.072 Uiso 1 1 calc R . . C25 C -0.3142(5) 0.5210(3) 0.0562(3) 0.0585(15) Uani 1 1 d . . . H25A H -0.2998 0.5098 0.0118 0.070 Uiso 1 1 calc R . . H25B H -0.4204 0.5173 0.0599 0.070 Uiso 1 1 calc R . . C26 C -0.2173(5) 0.4824(2) 0.1074(2) 0.0475(13) Uani 1 1 d . . . H26 H -0.2714 0.4453 0.1169 0.057 Uiso 1 1 calc R . . C27 C -0.1794(5) 0.5216(2) 0.1693(2) 0.0470(13) Uani 1 1 d . . . H27 H -0.2289 0.5059 0.2053 0.056 Uiso 1 1 calc R . . C28 C -0.0092(5) 0.5176(3) 0.1867(3) 0.0532(14) Uani 1 1 d . . . C29 C -0.0671(6) 0.4666(2) 0.0887(3) 0.0486(13) Uani 1 1 d . . . C30 C 0.2065(5) 0.4806(2) 0.1333(3) 0.0551(14) Uani 1 1 d . . . H30A H 0.2624 0.5116 0.1607 0.066 Uiso 1 1 calc R . . H30B H 0.2219 0.4876 0.0881 0.066 Uiso 1 1 calc R . . C31 C 0.2698(5) 0.4190(2) 0.1550(3) 0.0489(13) Uani 1 1 d . . . H31 H 0.2006 0.3876 0.1340 0.059 Uiso 1 1 calc R . . C32 C 0.4231(6) 0.4100(3) 0.1329(3) 0.0635(16) Uani 1 1 d . . . H32A H 0.4106 0.4123 0.0851 0.076 Uiso 1 1 calc R . . H32B H 0.4900 0.4428 0.1506 0.076 Uiso 1 1 calc R . . C33 C 0.4956(7) 0.3497(3) 0.1549(3) 0.0735(18) Uani 1 1 d . . . H33A H 0.5934 0.3467 0.1405 0.088 Uiso 1 1 calc R . . H33B H 0.4329 0.3165 0.1348 0.088 Uiso 1 1 calc R . . C34 C 0.5148(6) 0.3443(3) 0.2293(3) 0.0719(17) Uani 1 1 d . . . H34A H 0.5837 0.3755 0.2494 0.086 Uiso 1 1 calc R . . H34B H 0.5574 0.3047 0.2429 0.086 Uiso 1 1 calc R . . C35 C 0.3623(7) 0.3515(3) 0.2522(3) 0.0797(19) Uani 1 1 d . . . H35A H 0.2972 0.3178 0.2355 0.096 Uiso 1 1 calc R . . H35B H 0.3761 0.3502 0.3001 0.096 Uiso 1 1 calc R . . C36 C 0.2879(6) 0.4105(3) 0.2288(3) 0.0629(15) Uani 1 1 d . . . H36A H 0.3475 0.4441 0.2501 0.075 Uiso 1 1 calc R . . H36B H 0.1891 0.4123 0.2424 0.075 Uiso 1 1 calc R . . C37 C -0.0957(5) 0.7103(2) 0.2679(3) 0.0493(13) Uani 1 1 d . . . C38 C -0.1234(6) 0.7153(2) 0.3309(3) 0.0566(14) Uani 1 1 d . . . H38 H -0.1916 0.6893 0.3467 0.068 Uiso 1 1 calc R . . C39 C -0.0489(7) 0.7596(3) 0.3710(3) 0.0630(15) Uani 1 1 d . . . C40 C 0.0495(7) 0.7988(3) 0.3499(3) 0.0665(16) Uani 1 1 d . . . H40 H 0.0969 0.8288 0.3779 0.080 Uiso 1 1 calc R . . C41 C 0.0781(6) 0.7937(3) 0.2868(3) 0.0678(16) Uani 1 1 d . . . H41 H 0.1468 0.8199 0.2716 0.081 Uiso 1 1 calc R . . C42 C 0.0052(6) 0.7496(3) 0.2454(3) 0.0577(14) Uani 1 1 d . . . H42 H 0.0243 0.7464 0.2022 0.069 Uiso 1 1 calc R . . H1 H 0.778(5) 0.150(2) 0.300(2) 0.037(14) Uiso 1 1 d . . . H3 H -0.263(6) 0.656(2) 0.238(2) 0.051(15) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.1156(6) 0.1210(7) 0.0761(5) 0.0070(4) 0.0394(4) 0.0664(5) Br2 0.1518(8) 0.1136(7) 0.0571(4) -0.0091(4) 0.0186(5) -0.0143(5) N1 0.028(2) 0.068(3) 0.038(2) -0.005(2) 0.0045(19) 0.008(2) N2 0.042(2) 0.056(3) 0.049(3) -0.005(2) 0.000(2) -0.011(2) N3 0.034(2) 0.064(3) 0.060(3) -0.013(2) 0.011(2) -0.007(2) N4 0.033(2) 0.054(3) 0.049(3) -0.006(2) 0.0039(19) -0.0001(19) O1 0.0347(18) 0.088(3) 0.046(2) -0.008(2) -0.0001(15) 0.0121(18) O2 0.065(2) 0.097(3) 0.046(2) -0.003(2) 0.0181(19) -0.024(2) O3 0.085(3) 0.092(3) 0.039(2) 0.001(2) -0.010(2) -0.015(2) O4 0.0372(19) 0.104(3) 0.090(3) -0.033(3) 0.028(2) -0.016(2) O5 0.058(2) 0.115(4) 0.064(3) -0.040(3) -0.018(2) 0.017(2) O6 0.070(2) 0.089(3) 0.057(2) -0.023(2) 0.014(2) 0.004(2) C1 0.033(3) 0.059(3) 0.041(3) -0.004(3) 0.006(2) -0.001(2) C2 0.033(2) 0.059(3) 0.039(3) -0.003(3) 0.003(2) -0.002(2) C3 0.060(3) 0.060(4) 0.048(3) 0.002(3) 0.009(3) -0.016(3) C4 0.061(3) 0.081(4) 0.039(3) 0.000(3) 0.014(3) -0.015(3) C5 0.048(3) 0.064(4) 0.041(3) -0.012(3) 0.014(2) 0.002(3) C6 0.040(3) 0.052(3) 0.033(3) 0.001(2) 0.006(2) 0.000(2) C7 0.048(3) 0.055(3) 0.035(3) -0.006(3) 0.005(2) -0.014(2) C8 0.061(3) 0.052(3) 0.044(3) -0.005(3) 0.008(3) -0.005(3) C9 0.046(3) 0.067(4) 0.063(4) -0.009(3) 0.000(3) -0.003(3) C10 0.048(3) 0.075(5) 0.112(6) -0.012(4) 0.005(4) -0.010(3) C11 0.043(3) 0.084(5) 0.124(6) 0.003(4) -0.003(4) -0.016(3) C12 0.086(6) 0.173(10) 0.174(10) -0.024(8) 0.034(6) -0.067(6) C13 0.103(6) 0.130(7) 0.153(8) -0.086(6) 0.067(6) -0.068(5) C14 0.092(5) 0.067(5) 0.119(6) -0.010(4) 0.036(4) -0.015(4) C15 0.081(5) 0.090(6) 0.204(10) -0.030(6) 0.068(6) -0.026(4) C16 0.035(2) 0.048(3) 0.040(3) -0.007(2) 0.002(2) -0.001(2) C17 0.050(3) 0.070(4) 0.048(3) -0.004(3) -0.001(3) 0.014(3) C18 0.067(4) 0.090(5) 0.040(3) 0.002(3) -0.006(3) 0.015(3) C19 0.076(4) 0.072(4) 0.037(3) -0.012(3) 0.008(3) 0.007(3) C20 0.056(3) 0.052(3) 0.050(3) 0.000(3) 0.015(3) 0.008(3) C21 0.047(3) 0.047(3) 0.037(3) 0.003(2) 0.003(2) 0.008(2) C22 0.032(3) 0.073(4) 0.054(3) -0.008(3) 0.002(2) 0.000(3) C23 0.029(2) 0.060(3) 0.049(3) -0.009(3) 0.006(2) 0.002(2) C24 0.046(3) 0.081(4) 0.050(3) 0.005(3) -0.001(3) 0.012(3) C25 0.045(3) 0.078(4) 0.050(3) -0.012(3) -0.002(3) -0.005(3) C26 0.037(3) 0.056(3) 0.047(3) -0.005(3) -0.001(2) -0.014(2) C27 0.037(3) 0.061(3) 0.045(3) -0.003(3) 0.010(2) -0.004(2) C28 0.040(3) 0.071(4) 0.046(3) -0.008(3) 0.000(3) 0.002(3) C29 0.053(3) 0.051(3) 0.042(3) 0.000(3) 0.009(3) -0.002(3) C30 0.042(3) 0.060(4) 0.066(4) 0.007(3) 0.017(3) 0.002(2) C31 0.041(3) 0.048(3) 0.060(3) 0.002(3) 0.015(2) 0.000(2) C32 0.050(3) 0.085(4) 0.060(4) 0.013(3) 0.022(3) 0.019(3) C33 0.060(3) 0.083(5) 0.079(4) 0.010(4) 0.019(3) 0.019(3) C34 0.057(3) 0.077(4) 0.080(4) 0.012(4) 0.005(3) 0.007(3) C35 0.086(4) 0.085(5) 0.072(4) 0.026(4) 0.022(4) 0.008(4) C36 0.063(3) 0.070(4) 0.059(4) 0.003(3) 0.020(3) 0.008(3) C37 0.036(3) 0.051(3) 0.060(3) -0.002(3) 0.006(2) 0.003(2) C38 0.051(3) 0.054(4) 0.065(4) -0.001(3) 0.010(3) 0.001(3) C39 0.068(4) 0.066(4) 0.053(3) 0.003(3) 0.006(3) 0.003(3) C40 0.061(4) 0.063(4) 0.070(4) -0.005(3) -0.009(3) 0.000(3) C41 0.054(3) 0.061(4) 0.089(5) 0.001(4) 0.014(3) -0.012(3) C42 0.049(3) 0.064(4) 0.062(4) -0.007(3) 0.014(3) -0.003(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 Br1 C20 1.875(5) . ? Br2 C39 1.867(6) . ? N1 C1 1.341(6) . ? N1 C16 1.385(6) . ? N1 H1 0.80(4) . ? N2 C7 1.372(6) . ? N2 C8 1.372(7) . ? N2 C9 1.463(6) . ? N3 C22 1.329(7) . ? N3 C37 1.390(6) . ? N3 H3 0.85(5) . ? N4 C28 1.365(6) . ? N4 C29 1.377(6) . ? N4 C30 1.467(6) . ? O1 C1 1.236(5) . ? O2 C7 1.198(6) . ? O3 C8 1.192(6) . ? O4 C22 1.215(6) . ? O5 C28 1.192(6) . ? O6 C29 1.179(6) . ? C1 C2 1.482(7) . ? C2 C3 1.527(7) . ? C2 C6 1.542(7) . ? C2 H2 0.9800 . ? C3 C4 1.493(7) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.531(7) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.518(6) . ? C5 C8 1.520(7) . ? C5 H5 0.9800 . ? C6 C7 1.498(7) . ? C6 H6 0.9800 . ? C9 C10 1.477(8) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C15 1.373(9) . ? C10 C11 1.536(8) . ? C10 H10 0.9800 . ? C11 C12 1.541(10) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.392(11) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.535(10) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.541(9) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C21 1.369(6) . ? C16 C17 1.398(7) . ? C17 C18 1.345(7) . ? C17 H17 0.9300 . ? C18 C19 1.378(7) . ? C18 H18 0.9300 . ? C19 C20 1.361(7) . ? C19 H19 0.9300 . ? C20 C21 1.357(7) . ? C21 H21 0.9300 . ? C22 C23 1.511(7) . ? C23 C24 1.519(7) . ? C23 C27 1.554(7) . ? C23 H23 0.9800 . ? C24 C25 1.500(8) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.513(7) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C29 1.495(7) . ? C26 C27 1.526(7) . ? C26 H26 0.9800 . ? C27 C28 1.514(7) . ? C27 H27 0.9800 . ? C30 C31 1.503(7) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C36 1.507(7) . ? C31 C32 1.524(7) . ? C31 H31 0.9800 . ? C32 C33 1.509(8) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C34 1.511(8) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.521(8) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36 1.498(8) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 C38 1.357(8) . ? C37 C42 1.380(7) . ? C38 C39 1.375(8) . ? C38 H38 0.9300 . ? C39 C40 1.350(8) . ? C40 C41 1.360(8) . ? C40 H40 0.9300 . ? C41 C42 1.381(8) . ? C41 H41 0.9300 . ? C42 H42 0.9300 . ? 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 C16 127.1(4) . . ? C1 N1 H1 115(3) . . ? C16 N1 H1 117(3) . . ? C7 N2 C8 112.3(4) . . ? C7 N2 C9 123.6(4) . . ? C8 N2 C9 124.1(4) . . ? C22 N3 C37 126.2(5) . . ? C22 N3 H3 116(3) . . ? C37 N3 H3 118(3) . . ? C28 N4 C29 113.0(4) . . ? C28 N4 C30 124.0(4) . . ? C29 N4 C30 123.0(4) . . ? O1 C1 N1 123.1(5) . . ? O1 C1 C2 121.5(4) . . ? N1 C1 C2 115.3(4) . . ? C1 C2 C3 111.9(4) . . ? C1 C2 C6 113.5(4) . . ? C3 C2 C6 104.0(4) . . ? C1 C2 H2 109.1 . . ? C3 C2 H2 109.1 . . ? C6 C2 H2 109.1 . . ? C4 C3 C2 103.5(4) . . ? C4 C3 H3A 111.1 . . ? C2 C3 H3A 111.1 . . ? C4 C3 H3B 111.1 . . ? C2 C3 H3B 111.1 . . ? H3A C3 H3B 109.0 . . ? C3 C4 C5 103.4(4) . . ? C3 C4 H4A 111.1 . . ? C5 C4 H4A 111.1 . . ? C3 C4 H4B 111.1 . . ? C5 C4 H4B 111.1 . . ? H4A C4 H4B 109.0 . . ? C6 C5 C8 104.2(4) . . ? C6 C5 C4 106.4(4) . . ? C8 C5 C4 111.8(5) . . ? C6 C5 H5 111.4 . . ? C8 C5 H5 111.4 . . ? C4 C5 H5 111.4 . . ? C7 C6 C5 104.6(4) . . ? C7 C6 C2 114.4(4) . . ? C5 C6 C2 105.6(4) . . ? C7 C6 H6 110.6 . . ? C5 C6 H6 110.6 . . ? C2 C6 H6 110.6 . . ? O2 C7 N2 123.0(5) . . ? O2 C7 C6 127.5(4) . . ? N2 C7 C6 109.4(4) . . ? O3 C8 N2 123.1(5) . . ? O3 C8 C5 128.2(5) . . ? N2 C8 C5 108.7(4) . . ? N2 C9 C10 115.3(4) . . ? N2 C9 H9A 108.4 . . ? C10 C9 H9A 108.4 . . ? N2 C9 H9B 108.4 . . ? C10 C9 H9B 108.4 . . ? H9A C9 H9B 107.5 . . ? C15 C10 C9 120.5(6) . . ? C15 C10 C11 112.3(6) . . ? C9 C10 C11 110.4(5) . . ? C15 C10 H10 103.9 . . ? C9 C10 H10 103.9 . . ? C11 C10 H10 103.9 . . ? C10 C11 C12 111.4(6) . . ? C10 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? C10 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C13 C12 C11 111.9(8) . . ? C13 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? C13 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C12 C13 C14 112.3(6) . . ? C12 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? C12 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.9 . . ? C13 C14 C15 109.0(6) . . ? C13 C14 H14A 109.9 . . ? C15 C14 H14A 109.9 . . ? C13 C14 H14B 109.9 . . ? C15 C14 H14B 109.9 . . ? H14A C14 H14B 108.3 . . ? C10 C15 C14 116.9(7) . . ? C10 C15 H15A 108.1 . . ? C14 C15 H15A 108.1 . . ? C10 C15 H15B 108.1 . . ? C14 C15 H15B 108.1 . . ? H15A C15 H15B 107.3 . . ? C21 C16 N1 123.3(4) . . ? C21 C16 C17 119.7(5) . . ? N1 C16 C17 117.0(4) . . ? C18 C17 C16 119.1(5) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C17 C18 C19 121.6(5) . . ? C17 C18 H18 119.2 . . ? C19 C18 H18 119.2 . . ? C20 C19 C18 118.4(5) . . ? C20 C19 H19 120.8 . . ? C18 C19 H19 120.8 . . ? C21 C20 C19 121.8(5) . . ? C21 C20 Br1 119.1(4) . . ? C19 C20 Br1 119.1(4) . . ? C20 C21 C16 119.4(4) . . ? C20 C21 H21 120.3 . . ? C16 C21 H21 120.3 . . ? O4 C22 N3 123.4(5) . . ? O4 C22 C23 121.0(5) . . ? N3 C22 C23 115.5(5) . . ? C22 C23 C24 113.6(4) . . ? C22 C23 C27 113.4(4) . . ? C24 C23 C27 103.5(4) . . ? C22 C23 H23 108.7 . . ? C24 C23 H23 108.7 . . ? C27 C23 H23 108.7 . . ? C25 C24 C23 104.2(4) . . ? C25 C24 H24A 110.9 . . ? C23 C24 H24A 110.9 . . ? C25 C24 H24B 110.9 . . ? C23 C24 H24B 110.9 . . ? H24A C24 H24B 108.9 . . ? C24 C25 C26 102.6(4) . . ? C24 C25 H25A 111.2 . . ? C26 C25 H25A 111.2 . . ? C24 C25 H25B 111.2 . . ? C26 C25 H25B 111.2 . . ? H25A C25 H25B 109.2 . . ? C29 C26 C25 113.1(4) . . ? C29 C26 C27 104.6(4) . . ? C25 C26 C27 106.9(4) . . ? C29 C26 H26 110.7 . . ? C25 C26 H26 110.7 . . ? C27 C26 H26 110.7 . . ? C28 C27 C26 104.4(4) . . ? C28 C27 C23 113.7(4) . . ? C26 C27 C23 105.2(4) . . ? C28 C27 H27 111.1 . . ? C26 C27 H27 111.1 . . ? C23 C27 H27 111.1 . . ? O5 C28 N4 124.4(5) . . ? O5 C28 C27 127.1(5) . . ? N4 C28 C27 108.5(4) . . ? O6 C29 N4 123.7(5) . . ? O6 C29 C26 127.3(5) . . ? N4 C29 C26 109.0(4) . . ? N4 C30 C31 114.0(4) . . ? N4 C30 H30A 108.8 . . ? C31 C30 H30A 108.8 . . ? N4 C30 H30B 108.8 . . ? C31 C30 H30B 108.8 . . ? H30A C30 H30B 107.7 . . ? C30 C31 C36 112.6(5) . . ? C30 C31 C32 110.2(4) . . ? C36 C31 C32 108.7(4) . . ? C30 C31 H31 108.4 . . ? C36 C31 H31 108.4 . . ? C32 C31 H31 108.4 . . ? C33 C32 C31 113.0(5) . . ? C33 C32 H32A 109.0 . . ? C31 C32 H32A 109.0 . . ? C33 C32 H32B 109.0 . . ? C31 C32 H32B 109.0 . . ? H32A C32 H32B 107.8 . . ? C32 C33 C34 110.3(5) . . ? C32 C33 H33A 109.6 . . ? C34 C33 H33A 109.6 . . ? C32 C33 H33B 109.6 . . ? C34 C33 H33B 109.6 . . ? H33A C33 H33B 108.1 . . ? C33 C34 C35 109.7(5) . . ? C33 C34 H34A 109.7 . . ? C35 C34 H34A 109.7 . . ? C33 C34 H34B 109.7 . . ? C35 C34 H34B 109.7 . . ? H34A C34 H34B 108.2 . . ? C36 C35 C34 111.6(5) . . ? C36 C35 H35A 109.3 . . ? C34 C35 H35A 109.3 . . ? C36 C35 H35B 109.3 . . ? C34 C35 H35B 109.3 . . ? H35A C35 H35B 108.0 . . ? C35 C36 C31 113.6(5) . . ? C35 C36 H36A 108.8 . . ? C31 C36 H36A 108.8 . . ? C35 C36 H36B 108.8 . . ? C31 C36 H36B 108.8 . . ? H36A C36 H36B 107.7 . . ? C38 C37 C42 119.6(5) . . ? C38 C37 N3 116.4(5) . . ? C42 C37 N3 124.0(5) . . ? C37 C38 C39 118.8(6) . . ? C37 C38 H38 120.6 . . ? C39 C38 H38 120.6 . . ? C40 C39 C38 122.6(6) . . ? C40 C39 Br2 119.1(5) . . ? C38 C39 Br2 118.2(5) . . ? C39 C40 C41 118.7(6) . . ? C39 C40 H40 120.6 . . ? C41 C40 H40 120.6 . . ? C40 C41 C42 120.1(6) . . ? C40 C41 H41 120.0 . . ? C42 C41 H41 120.0 . . ? C37 C42 C41 120.2(6) . . ? C37 C42 H42 119.9 . . ? C41 C42 H42 119.9 . . ? 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 C16 N1 C1 O1 3.4(8) . . . . ? C16 N1 C1 C2 -175.8(5) . . . . ? O1 C1 C2 C3 42.0(6) . . . . ? N1 C1 C2 C3 -138.7(4) . . . . ? O1 C1 C2 C6 -75.4(6) . . . . ? N1 C1 C2 C6 103.8(5) . . . . ? C1 C2 C3 C4 -160.6(4) . . . . ? C6 C2 C3 C4 -37.6(5) . . . . ? C2 C3 C4 C5 41.0(5) . . . . ? C3 C4 C5 C6 -29.0(5) . . . . ? C3 C4 C5 C8 84.2(5) . . . . ? C8 C5 C6 C7 8.3(5) . . . . ? C4 C5 C6 C7 126.6(4) . . . . ? C8 C5 C6 C2 -112.7(4) . . . . ? C4 C5 C6 C2 5.6(5) . . . . ? C1 C2 C6 C7 26.7(5) . . . . ? C3 C2 C6 C7 -95.2(5) . . . . ? C1 C2 C6 C5 141.2(4) . . . . ? C3 C2 C6 C5 19.3(5) . . . . ? C8 N2 C7 O2 -175.7(5) . . . . ? C9 N2 C7 O2 2.3(8) . . . . ? C8 N2 C7 C6 4.5(6) . . . . ? C9 N2 C7 C6 -177.5(5) . . . . ? C5 C6 C7 O2 172.0(6) . . . . ? C2 C6 C7 O2 -72.9(7) . . . . ? C5 C6 C7 N2 -8.2(5) . . . . ? C2 C6 C7 N2 106.9(5) . . . . ? C7 N2 C8 O3 -179.2(5) . . . . ? C9 N2 C8 O3 2.9(8) . . . . ? C7 N2 C8 C5 1.2(6) . . . . ? C9 N2 C8 C5 -176.8(5) . . . . ? C6 C5 C8 O3 174.2(5) . . . . ? C4 C5 C8 O3 59.7(7) . . . . ? C6 C5 C8 N2 -6.2(6) . . . . ? C4 C5 C8 N2 -120.7(5) . . . . ? C7 N2 C9 C10 -78.0(7) . . . . ? C8 N2 C9 C10 99.7(7) . . . . ? N2 C9 C10 C15 -42.9(9) . . . . ? N2 C9 C10 C11 -176.5(5) . . . . ? C15 C10 C11 C12 48.6(10) . . . . ? C9 C10 C11 C12 -173.9(7) . . . . ? C10 C11 C12 C13 -54.1(10) . . . . ? C11 C12 C13 C14 57.6(11) . . . . ? C12 C13 C14 C15 -53.5(11) . . . . ? C9 C10 C15 C14 178.4(6) . . . . ? C11 C10 C15 C14 -48.9(11) . . . . ? C13 C14 C15 C10 50.1(10) . . . . ? C1 N1 C16 C21 -27.7(8) . . . . ? C1 N1 C16 C17 152.9(5) . . . . ? C21 C16 C17 C18 -0.9(8) . . . . ? N1 C16 C17 C18 178.5(5) . . . . ? C16 C17 C18 C19 1.0(9) . . . . ? C17 C18 C19 C20 -1.4(9) . . . . ? C18 C19 C20 C21 1.7(9) . . . . ? C18 C19 C20 Br1 -179.3(4) . . . . ? C19 C20 C21 C16 -1.7(8) . . . . ? Br1 C20 C21 C16 179.3(4) . . . . ? N1 C16 C21 C20 -178.1(5) . . . . ? C17 C16 C21 C20 1.3(7) . . . . ? C37 N3 C22 O4 -2.0(9) . . . . ? C37 N3 C22 C23 174.5(5) . . . . ? O4 C22 C23 C24 -43.3(7) . . . . ? N3 C22 C23 C24 140.2(5) . . . . ? O4 C22 C23 C27 74.5(7) . . . . ? N3 C22 C23 C27 -102.0(5) . . . . ? C22 C23 C24 C25 160.6(4) . . . . ? C27 C23 C24 C25 37.2(5) . . . . ? C23 C24 C25 C26 -42.3(5) . . . . ? C24 C25 C26 C29 -83.6(5) . . . . ? C24 C25 C26 C27 31.0(5) . . . . ? C29 C26 C27 C28 -7.9(5) . . . . ? C25 C26 C27 C28 -128.1(4) . . . . ? C29 C26 C27 C23 112.0(4) . . . . ? C25 C26 C27 C23 -8.2(5) . . . . ? C22 C23 C27 C28 -27.4(6) . . . . ? C24 C23 C27 C28 96.1(5) . . . . ? C22 C23 C27 C26 -141.0(4) . . . . ? C24 C23 C27 C26 -17.4(5) . . . . ? C29 N4 C28 O5 177.4(6) . . . . ? C30 N4 C28 O5 -5.7(9) . . . . ? C29 N4 C28 C27 -3.6(6) . . . . ? C30 N4 C28 C27 173.3(4) . . . . ? C26 C27 C28 O5 -173.9(6) . . . . ? C23 C27 C28 O5 72.1(7) . . . . ? C26 C27 C28 N4 7.3(6) . . . . ? C23 C27 C28 N4 -106.8(5) . . . . ? C28 N4 C29 O6 178.1(5) . . . . ? C30 N4 C29 O6 1.2(8) . . . . ? C28 N4 C29 C26 -1.7(6) . . . . ? C30 N4 C29 C26 -178.7(4) . . . . ? C25 C26 C29 O6 -57.7(7) . . . . ? C27 C26 C29 O6 -173.6(5) . . . . ? C25 C26 C29 N4 122.2(4) . . . . ? C27 C26 C29 N4 6.2(5) . . . . ? C28 N4 C30 C31 101.3(6) . . . . ? C29 N4 C30 C31 -82.1(6) . . . . ? N4 C30 C31 C36 -73.2(6) . . . . ? N4 C30 C31 C32 165.2(4) . . . . ? C30 C31 C32 C33 178.2(5) . . . . ? C36 C31 C32 C33 54.4(6) . . . . ? C31 C32 C33 C34 -58.0(7) . . . . ? C32 C33 C34 C35 56.9(7) . . . . ? C33 C34 C35 C36 -56.0(7) . . . . ? C34 C35 C36 C31 55.5(7) . . . . ? C30 C31 C36 C35 -175.4(5) . . . . ? C32 C31 C36 C35 -53.0(6) . . . . ? C22 N3 C37 C38 -152.7(5) . . . . ? C22 N3 C37 C42 29.6(8) . . . . ? C42 C37 C38 C39 -0.3(8) . . . . ? N3 C37 C38 C39 -178.2(5) . . . . ? C37 C38 C39 C40 0.8(8) . . . . ? C37 C38 C39 Br2 177.9(4) . . . . ? C38 C39 C40 C41 -1.1(9) . . . . ? Br2 C39 C40 C41 -178.2(4) . . . . ? C39 C40 C41 C42 1.0(9) . . . . ? C38 C37 C42 C41 0.2(8) . . . . ? N3 C37 C42 C41 177.9(5) . . . . ? C40 C41 C42 C37 -0.6(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3 O1 0.85(5) 2.10(5) 2.881(6) 153(5) 2 N1 H1 O4 0.80(4) 2.17(4) 2.919(6) 155(4) 2_645 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.673 _refine_diff_density_min -0.644 _refine_diff_density_rms 0.069