# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Wen-Jing Xiao' _publ_contact_author_email WXIAO@MAIL.CCNU.EDU.CN _publ_section_title ; Highly Enantioselective Organocatalytic Michael Addition of Nitroalkanes to 4-Oxo-Enoates ; loop_ _publ_author_name 'Wen-Jing Xiao.' 'Hai-Hua Lu.' 'Xu-Fan Wang.' 'Hong Wu.' 'Chang-Jiang Yao.' ; Jian-Ming Zhang ; # Attachment 't.cif' data_t _database_code_depnum_ccdc_archive 'CCDC 712054' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 Br N O5' _chemical_formula_sum 'C18 H16 Br N O5' _chemical_formula_weight 406.23 _chemical_absolute_configuration ad 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 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.6235(8) _cell_length_b 39.442(6) _cell_length_c 8.0098(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.031(1) _cell_angle_gamma 90.00 _cell_volume 1776.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 2736 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 22.24 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 2.341 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine focus sealed Siemens Mo tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Apex CCD area-detector' _diffrn_measurement_method '0.3\% wide \w exposures' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8715 _diffrn_reflns_av_R_equivalents 0.0852 _diffrn_reflns_av_sigmaI/netI 0.0783 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -43 _diffrn_reflns_limit_k_max 48 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 25.99 _reflns_number_total 5418 _reflns_number_gt 3237 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker Version 5.628, 2001' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'SAINT+, Bruker Version 6.45, 2001' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material PLATON _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^)+(0.0813P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(2) _refine_ls_number_reflns 5418 _refine_ls_number_parameters 404 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0835 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1457 _refine_ls_wR_factor_gt 0.1200 _refine_ls_goodness_of_fit_ref 0.918 _refine_ls_restrained_S_all 0.918 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 Br2 Br 0.5464(3) 0.68796(2) 0.95895(17) 0.0972(4) Uani 1 1 d . . . Br1 Br 0.8237(2) 0.71613(3) 0.48268(18) 0.1011(5) Uani 1 1 d . . . C1 C 0.5169(9) 0.82043(11) 0.6494(8) 0.055(2) Uani 1 1 d G . . C2 C 0.7355(9) 0.81889(12) 0.5688(8) 0.058(2) Uani 1 1 d G . . H2 H 0.8208 0.8387 0.5487 0.070 Uiso 1 1 calc R . . C3 C 0.8265(8) 0.78778(14) 0.5181(7) 0.063(2) Uani 1 1 d G . . H3 H 0.9728 0.7868 0.4642 0.076 Uiso 1 1 calc R . . C4 C 0.6990(11) 0.75822(11) 0.5482(8) 0.063(2) Uani 1 1 d G . . C5 C 0.4804(10) 0.75976(12) 0.6288(8) 0.069(3) Uani 1 1 d G . . H5 H 0.3951 0.7400 0.6489 0.083 Uiso 1 1 calc R . . C6 C 0.3893(8) 0.79087(15) 0.6795(7) 0.058(2) Uani 1 1 d G . . H6 H 0.2431 0.7919 0.7334 0.070 Uiso 1 1 calc R . . C7 C 0.4061(17) 0.8530(2) 0.7027(11) 0.053(2) Uani 1 1 d . . . C8 C 0.5647(19) 0.8832(2) 0.7351(12) 0.062(2) Uani 1 1 d . . . H8A H 0.6982 0.8762 0.8038 0.074 Uiso 1 1 calc R . . H8B H 0.6270 0.8915 0.6300 0.074 Uiso 1 1 calc R . . C9 C 0.4321(17) 0.9110(2) 0.8214(13) 0.065(3) Uani 1 1 d . . . H9 H 0.3099 0.9195 0.7448 0.077 Uiso 1 1 calc R . . C10 C 0.598(2) 0.9402(2) 0.8626(14) 0.068(3) Uani 1 1 d . . . H10A H 0.6961 0.9337 0.9571 0.081 Uiso 1 1 calc R . . H10B H 0.7032 0.9439 0.7683 0.081 Uiso 1 1 calc R . . C11 C 0.3091(18) 0.8991(2) 0.9803(10) 0.053(2) Uani 1 1 d . . . C12 C 0.309(3) 0.8588(3) 1.2023(17) 0.115(6) Uani 1 1 d . . . H12A H 0.4264 0.8569 1.2903 0.138 Uiso 1 1 calc R . . H12B H 0.1827 0.8736 1.2414 0.138 Uiso 1 1 calc R . . C13 C 0.2113(16) 0.82565(17) 1.1664(11) 0.074(3) Uani 1 1 d G . . C14 C 0.3412(11) 0.7965(2) 1.2013(9) 0.079(3) Uani 1 1 d G . . H14 H 0.4851 0.7981 1.2580 0.095 Uiso 1 1 calc R . . C15 C 0.2561(19) 0.76502(18) 1.1515(11) 0.099(4) Uani 1 1 d G . . H15 H 0.3430 0.7455 1.1749 0.118 Uiso 1 1 calc R . . C16 C 0.041(2) 0.7627(3) 1.0668(10) 0.112(5) Uani 1 1 d G . . H16 H -0.0160 0.7416 1.0334 0.135 Uiso 1 1 calc R . . C17 C -0.0889(13) 0.7918(4) 1.0318(9) 0.124(6) Uani 1 1 d G . . H17 H -0.2328 0.7902 0.9751 0.149 Uiso 1 1 calc R . . C18 C -0.0038(15) 0.8233(3) 1.0817(11) 0.115(5) Uani 1 1 d G . . H18 H -0.0907 0.8428 1.0583 0.138 Uiso 1 1 calc R . . C25 C 0.9252(16) 0.5499(2) 0.7300(9) 0.044(2) Uani 1 1 d . . . C19 C 0.6586(10) 0.64593(10) 0.8877(8) 0.063(3) Uani 1 1 d G . . C20 C 0.8755(10) 0.64359(11) 0.8053(7) 0.062(3) Uani 1 1 d G . . H20 H 0.9633 0.6631 0.7836 0.074 Uiso 1 1 calc R . . C21 C 0.9611(8) 0.61214(13) 0.7552(6) 0.051(2) Uani 1 1 d G . . H21 H 1.1062 0.6106 0.7000 0.061 Uiso 1 1 calc R . . C22 C 0.8298(9) 0.58301(10) 0.7876(6) 0.0427(19) Uani 1 1 d G . . C23 C 0.6130(8) 0.58534(11) 0.8701(7) 0.054(2) Uani 1 1 d G . . H23 H 0.5251 0.5659 0.8917 0.064 Uiso 1 1 calc R . . C24 C 0.5274(8) 0.61680(14) 0.9201(7) 0.057(2) Uani 1 1 d G . . H24 H 0.3823 0.6184 0.9753 0.068 Uiso 1 1 calc R . . C26 C 0.7624(16) 0.5223(2) 0.6824(11) 0.052(2) Uani 1 1 d . . . H26A H 0.6383 0.5315 0.6115 0.062 Uiso 1 1 calc R . . H26B H 0.6872 0.5135 0.7824 0.062 Uiso 1 1 calc R . . C27 C 0.8848(16) 0.4929(2) 0.5900(10) 0.051(2) Uani 1 1 d . . . H27 H 0.7595 0.4790 0.5394 0.061 Uiso 1 1 calc R . . C28 C 1.026(2) 0.4703(2) 0.7031(11) 0.064(2) Uani 1 1 d . . . H28A H 1.1628 0.4828 0.7437 0.076 Uiso 1 1 calc R . . H28B H 0.9287 0.4645 0.7989 0.076 Uiso 1 1 calc R . . C29 C 1.044(2) 0.5060(3) 0.4470(13) 0.070(3) Uani 1 1 d . . . C30 C 1.058(3) 0.5479(3) 0.2283(13) 0.109(5) Uani 1 1 d . . . H30A H 0.9485 0.5510 0.1361 0.131 Uiso 1 1 calc R . . H30B H 1.1866 0.5334 0.1907 0.131 Uiso 1 1 calc R . . C31 C 1.1561(15) 0.58160(14) 0.2817(9) 0.067(3) Uani 1 1 d G . . C32 C 1.3686(14) 0.5856(3) 0.3680(10) 0.104(5) Uani 1 1 d G . . H32 H 1.4597 0.5668 0.3955 0.125 Uiso 1 1 calc R . . C33 C 1.4450(12) 0.6179(3) 0.4134(9) 0.131(7) Uani 1 1 d G . . H33 H 1.5872 0.6205 0.4711 0.157 Uiso 1 1 calc R . . C34 C 1.3088(18) 0.6461(2) 0.3724(9) 0.114(6) Uani 1 1 d G . . H34 H 1.3599 0.6676 0.4027 0.137 Uiso 1 1 calc R . . C35 C 1.0963(16) 0.64204(14) 0.2860(9) 0.082(3) Uani 1 1 d G . . H35 H 1.0051 0.6609 0.2586 0.098 Uiso 1 1 calc R . . C36 C 1.0199(10) 0.60981(17) 0.2407(7) 0.060(2) Uani 1 1 d G . . H36 H 0.8777 0.6071 0.1829 0.072 Uiso 1 1 calc R . . N1 N 0.479(2) 0.9722(2) 0.9024(11) 0.069(3) Uani 1 1 d . . . N2 N 1.110(2) 0.4387(2) 0.6243(12) 0.082(3) Uani 1 1 d . . . O1 O 0.1970(14) 0.85518(19) 0.7201(10) 0.078(2) Uani 1 1 d . . . O2 O 0.5809(18) 0.9919(2) 0.9952(11) 0.101(3) Uani 1 1 d . . . O3 O 0.287(2) 0.9787(3) 0.8416(15) 0.122(4) Uani 1 1 d . . . O4 O 0.4220(14) 0.87392(17) 1.0487(9) 0.0757(19) Uani 1 1 d . . . O5 O 0.1353(16) 0.9123(2) 1.0384(10) 0.102(3) Uani 1 1 d . . . O6 O 1.1413(12) 0.54614(17) 0.7212(9) 0.072(2) Uani 1 1 d . . . O7 O 0.989(2) 0.4244(2) 0.5213(11) 0.105(3) Uani 1 1 d . . . O9 O 0.9362(17) 0.53210(17) 0.3663(8) 0.082(2) Uani 1 1 d . . . O10 O 1.2313(15) 0.49447(19) 0.4085(9) 0.084(2) Uani 1 1 d . . . O8 O 1.301(2) 0.4271(3) 0.6703(12) 0.124(4) Uani 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 Br2 0.1148(9) 0.0598(6) 0.1169(10) -0.0073(7) 0.0237(8) 0.0164(6) Br1 0.1158(9) 0.0610(6) 0.1264(11) -0.0098(7) 0.0201(9) 0.0149(6) C1 0.045(5) 0.059(6) 0.062(6) 0.002(4) 0.000(5) -0.001(5) C2 0.046(5) 0.064(6) 0.065(6) -0.003(5) 0.007(4) -0.008(4) C3 0.058(5) 0.066(6) 0.065(6) 0.001(5) -0.005(5) -0.006(5) C4 0.062(6) 0.053(5) 0.074(6) -0.007(5) -0.007(6) 0.013(5) C5 0.069(7) 0.077(7) 0.062(6) 0.006(5) 0.014(6) -0.019(6) C6 0.059(6) 0.052(5) 0.063(6) -0.007(5) 0.006(5) -0.004(5) C7 0.039(5) 0.061(6) 0.058(6) -0.003(4) -0.002(4) -0.003(4) C8 0.072(6) 0.051(5) 0.062(6) 0.010(4) 0.022(5) -0.001(5) C9 0.053(5) 0.039(5) 0.102(7) 0.018(5) 0.013(5) 0.016(4) C10 0.078(7) 0.047(5) 0.079(7) 0.007(4) 0.014(6) 0.007(5) C11 0.087(7) 0.030(4) 0.042(5) -0.001(4) 0.018(5) -0.001(4) C12 0.190(16) 0.068(8) 0.088(9) -0.010(7) 0.057(10) 0.013(10) C13 0.071(7) 0.086(8) 0.065(7) 0.029(5) 0.009(6) -0.004(6) C14 0.062(7) 0.081(8) 0.094(8) 0.015(6) 0.002(6) 0.010(6) C15 0.120(12) 0.076(9) 0.100(10) -0.002(7) 0.015(9) 0.029(8) C16 0.119(12) 0.158(15) 0.061(8) -0.004(8) 0.023(8) -0.074(11) C17 0.059(7) 0.25(2) 0.060(8) 0.030(12) 0.006(6) -0.037(11) C18 0.074(9) 0.136(14) 0.135(12) 0.045(10) -0.010(9) 0.000(8) C25 0.048(5) 0.062(5) 0.021(4) 0.005(3) -0.001(4) -0.002(4) C19 0.065(6) 0.067(6) 0.058(6) 0.007(5) 0.000(5) 0.017(5) C20 0.056(6) 0.036(5) 0.093(7) 0.015(4) 0.003(5) -0.002(4) C21 0.044(4) 0.062(5) 0.046(5) 0.011(4) -0.006(4) 0.003(5) C22 0.042(5) 0.055(5) 0.032(4) -0.001(3) -0.001(4) -0.006(4) C23 0.042(5) 0.053(5) 0.066(6) 0.003(4) -0.008(5) -0.006(4) C24 0.042(5) 0.057(6) 0.072(6) -0.008(4) 0.014(5) 0.004(4) C26 0.050(5) 0.054(5) 0.050(5) 0.006(4) 0.006(4) -0.014(4) C27 0.056(5) 0.056(5) 0.041(5) 0.009(4) -0.007(4) 0.005(4) C28 0.084(6) 0.042(5) 0.065(5) 0.000(4) -0.002(6) 0.003(5) C29 0.086(8) 0.065(7) 0.059(6) -0.019(5) 0.008(6) -0.009(6) C30 0.190(16) 0.090(9) 0.049(6) 0.029(6) 0.003(8) 0.012(10) C31 0.079(7) 0.052(6) 0.071(6) 0.020(5) 0.010(6) 0.017(5) C32 0.059(8) 0.161(15) 0.092(9) 0.060(9) 0.010(7) 0.046(9) C33 0.057(7) 0.24(2) 0.094(10) 0.047(13) -0.022(7) -0.025(12) C34 0.137(13) 0.162(15) 0.043(7) 0.008(7) 0.019(8) -0.083(12) C35 0.089(8) 0.075(8) 0.082(8) 0.013(6) 0.016(7) 0.011(7) C36 0.066(6) 0.060(6) 0.055(5) -0.001(4) 0.011(5) -0.008(5) N1 0.104(7) 0.041(4) 0.063(5) 0.013(4) 0.016(5) 0.008(5) N2 0.133(10) 0.070(6) 0.043(5) 0.018(4) 0.013(6) 0.012(6) O1 0.053(4) 0.077(5) 0.104(6) -0.013(4) -0.017(4) 0.002(4) O2 0.139(7) 0.077(5) 0.088(5) -0.017(5) 0.006(6) -0.005(5) O3 0.121(8) 0.090(7) 0.154(9) 0.002(6) -0.024(7) 0.043(6) O4 0.096(5) 0.068(4) 0.063(4) 0.011(3) 0.005(4) 0.006(4) O5 0.129(7) 0.082(5) 0.096(6) 0.018(5) 0.049(6) 0.035(5) O6 0.051(4) 0.060(4) 0.105(6) -0.023(4) 0.003(4) 0.002(3) O7 0.180(10) 0.061(5) 0.074(5) -0.019(4) -0.006(6) 0.015(6) O9 0.142(7) 0.045(3) 0.059(4) 0.018(3) 0.002(4) 0.007(4) O10 0.095(6) 0.080(5) 0.076(5) -0.018(4) 0.044(5) -0.001(4) O8 0.141(9) 0.134(9) 0.097(7) -0.017(6) -0.013(6) 0.072(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 Br2 C19 1.863(4) . no Br1 C4 1.877(4) . no C1 C2 1.3900 . no C1 C6 1.3900 . no C1 C7 1.489(10) . no C2 C3 1.3900 . no C2 H2 0.9300 . no C3 C4 1.3900 . no C3 H3 0.9300 . no C4 C5 1.3900 . no C5 C6 1.3900 . no C5 H5 0.9300 . no C6 H6 0.9300 . no C7 O1 1.187(11) . no C7 C8 1.510(14) . no C8 C9 1.497(13) . no C8 H8A 0.9700 . no C8 H8B 0.9700 . no C9 C10 1.517(15) . no C9 C11 1.524(13) . no C9 H9 0.9800 . no C10 N1 1.466(12) . no C10 H10A 0.9700 . no C10 H10B 0.9700 . no C11 O5 1.201(11) . no C11 O4 1.298(11) . no C12 C13 1.446(16) . no C12 O4 1.508(15) . no C12 H12A 0.9700 . no C12 H12B 0.9700 . no C13 C14 1.3900 . no C13 C18 1.3900 . no C14 C15 1.3900 . no C14 H14 0.9300 . no C15 C16 1.3900 . no C15 H15 0.9300 . no C16 C17 1.3900 . no C16 H16 0.9300 . no C17 C18 1.3900 . no C17 H17 0.9300 . no C18 H18 0.9300 . no C25 O6 1.227(11) . no C25 C26 1.473(12) . no C25 C22 1.485(10) . no C19 C20 1.3900 . no C19 C24 1.3900 . no C20 C21 1.3900 . no C20 H20 0.9300 . no C21 C22 1.3900 . no C21 H21 0.9300 . no C22 C23 1.3900 . no C23 C24 1.3900 . no C23 H23 0.9300 . no C24 H24 0.9300 . no C26 C27 1.538(13) . no C26 H26A 0.9700 . no C26 H26B 0.9700 . no C27 C28 1.500(12) . no C27 C29 1.544(14) . no C27 H27 0.9800 . no C28 N2 1.475(13) . no C28 H28A 0.9700 . no C28 H28B 0.9700 . no C29 O10 1.187(13) . no C29 O9 1.358(14) . no C30 O9 1.442(14) . no C30 C31 1.501(15) . no C30 H30A 0.9700 . no C30 H30B 0.9700 . no C31 C32 1.3900 . no C31 C36 1.3900 . no C32 C33 1.3900 . no C32 H32 0.9300 . no C33 C34 1.3900 . no C33 H33 0.9300 . no C34 C35 1.3900 . no C34 H34 0.9300 . no C35 C36 1.3900 . no C35 H35 0.9300 . no C36 H36 0.9300 . no N1 O3 1.210(14) . no N1 O2 1.219(12) . no N2 O7 1.209(13) . no N2 O8 1.224(14) . no 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 C2 C1 C6 120.0 . . no C2 C1 C7 122.8(5) . . no C6 C1 C7 117.2(5) . . no C3 C2 C1 120.0 . . no C3 C2 H2 120.0 . . no C1 C2 H2 120.0 . . no C4 C3 C2 120.0 . . no C4 C3 H3 120.0 . . no C2 C3 H3 120.0 . . no C3 C4 C5 120.0 . . no C3 C4 Br1 120.1(3) . . no C5 C4 Br1 119.9(3) . . no C4 C5 C6 120.0 . . no C4 C5 H5 120.0 . . no C6 C5 H5 120.0 . . no C5 C6 C1 120.0 . . no C5 C6 H6 120.0 . . no C1 C6 H6 120.0 . . no O1 C7 C1 120.8(8) . . no O1 C7 C8 120.4(9) . . no C1 C7 C8 118.8(7) . . no C9 C8 C7 111.4(8) . . no C9 C8 H8A 109.4 . . no C7 C8 H8A 109.4 . . no C9 C8 H8B 109.4 . . no C7 C8 H8B 109.4 . . no H8A C8 H8B 108.0 . . no C8 C9 C10 110.5(8) . . no C8 C9 C11 112.6(7) . . no C10 C9 C11 109.4(8) . . no C8 C9 H9 108.1 . . no C10 C9 H9 108.1 . . no C11 C9 H9 108.1 . . no N1 C10 C9 114.8(9) . . no N1 C10 H10A 108.6 . . no C9 C10 H10A 108.6 . . no N1 C10 H10B 108.6 . . no C9 C10 H10B 108.6 . . no H10A C10 H10B 107.6 . . no O5 C11 O4 124.4(8) . . no O5 C11 C9 123.9(8) . . no O4 C11 C9 111.5(8) . . no C13 C12 O4 110.8(9) . . no C13 C12 H12A 109.5 . . no O4 C12 H12A 109.5 . . no C13 C12 H12B 109.5 . . no O4 C12 H12B 109.5 . . no H12A C12 H12B 108.1 . . no C14 C13 C18 120.0 . . no C14 C13 C12 120.6(10) . . no C18 C13 C12 119.1(10) . . no C15 C14 C13 120.0 . . no C15 C14 H14 120.0 . . no C13 C14 H14 120.0 . . no C14 C15 C16 120.0 . . no C14 C15 H15 120.0 . . no C16 C15 H15 120.0 . . no C17 C16 C15 120.0 . . no C17 C16 H16 120.0 . . no C15 C16 H16 120.0 . . no C16 C17 C18 120.0 . . no C16 C17 H17 120.0 . . no C18 C17 H17 120.0 . . no C17 C18 C13 120.0 . . no C17 C18 H18 120.0 . . no C13 C18 H18 120.0 . . no O6 C25 C26 120.7(8) . . no O6 C25 C22 118.9(8) . . no C26 C25 C22 120.4(7) . . no C20 C19 C24 120.0 . . no C20 C19 Br2 120.1(3) . . no C24 C19 Br2 119.9(3) . . no C19 C20 C21 120.0 . . no C19 C20 H20 120.0 . . no C21 C20 H20 120.0 . . no C20 C21 C22 120.0 . . no C20 C21 H21 120.0 . . no C22 C21 H21 120.0 . . no C23 C22 C21 120.0 . . no C23 C22 C25 121.5(5) . . no C21 C22 C25 118.5(5) . . no C22 C23 C24 120.0 . . no C22 C23 H23 120.0 . . no C24 C23 H23 120.0 . . no C23 C24 C19 120.0 . . no C23 C24 H24 120.0 . . no C19 C24 H24 120.0 . . no C25 C26 C27 113.8(7) . . no C25 C26 H26A 108.8 . . no C27 C26 H26A 108.8 . . no C25 C26 H26B 108.8 . . no C27 C26 H26B 108.8 . . no H26A C26 H26B 107.7 . . no C28 C27 C26 113.3(7) . . no C28 C27 C29 109.9(8) . . no C26 C27 C29 111.4(7) . . no C28 C27 H27 107.4 . . no C26 C27 H27 107.4 . . no C29 C27 H27 107.4 . . no N2 C28 C27 114.5(8) . . no N2 C28 H28A 108.6 . . no C27 C28 H28A 108.6 . . no N2 C28 H28B 108.6 . . no C27 C28 H28B 108.6 . . no H28A C28 H28B 107.6 . . no O10 C29 O9 124.4(11) . . no O10 C29 C27 125.3(11) . . no O9 C29 C27 110.3(10) . . no O9 C30 C31 109.8(8) . . no O9 C30 H30A 109.7 . . no C31 C30 H30A 109.7 . . no O9 C30 H30B 109.7 . . no C31 C30 H30B 109.7 . . no H30A C30 H30B 108.2 . . no C32 C31 C36 120.0 . . no C32 C31 C30 124.0(9) . . no C36 C31 C30 116.0(9) . . no C33 C32 C31 120.0 . . no C33 C32 H32 120.0 . . no C31 C32 H32 120.0 . . no C32 C33 C34 120.0 . . no C32 C33 H33 120.0 . . no C34 C33 H33 120.0 . . no C35 C34 C33 120.0 . . no C35 C34 H34 120.0 . . no C33 C34 H34 120.0 . . no C36 C35 C34 120.0 . . no C36 C35 H35 120.0 . . no C34 C35 H35 120.0 . . no C35 C36 C31 120.0 . . no C35 C36 H36 120.0 . . no C31 C36 H36 120.0 . . no O3 N1 O2 122.0(10) . . no O3 N1 C10 120.2(11) . . no O2 N1 C10 117.8(11) . . no O7 N2 O8 121.9(12) . . no O7 N2 C28 120.3(12) . . no O8 N2 C28 117.8(12) . . no C11 O4 C12 116.0(9) . . no C29 O9 C30 118.6(10) . . no 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 C6 C1 C2 C3 0.0 . . . . no C7 C1 C2 C3 -178.3(7) . . . . no C1 C2 C3 C4 0.0 . . . . no C2 C3 C4 C5 0.0 . . . . no C2 C3 C4 Br1 -179.1(5) . . . . no C3 C4 C5 C6 0.0 . . . . no Br1 C4 C5 C6 179.1(5) . . . . no C4 C5 C6 C1 0.0 . . . . no C2 C1 C6 C5 0.0 . . . . no C7 C1 C6 C5 178.4(7) . . . . no C2 C1 C7 O1 155.4(8) . . . . no C6 C1 C7 O1 -22.9(12) . . . . no C2 C1 C7 C8 -24.9(10) . . . . no C6 C1 C7 C8 156.8(6) . . . . no O1 C7 C8 C9 11.8(13) . . . . no C1 C7 C8 C9 -167.9(8) . . . . no C7 C8 C9 C10 176.4(8) . . . . no C7 C8 C9 C11 53.7(11) . . . . no C8 C9 C10 N1 163.3(9) . . . . no C11 C9 C10 N1 -72.2(10) . . . . no C8 C9 C11 O5 -153.9(10) . . . . no C10 C9 C11 O5 82.8(12) . . . . no C8 C9 C11 O4 29.1(12) . . . . no C10 C9 C11 O4 -94.2(9) . . . . no O4 C12 C13 C14 96.3(12) . . . . no O4 C12 C13 C18 -77.5(13) . . . . no C18 C13 C14 C15 0.0 . . . . no C12 C13 C14 C15 -173.7(9) . . . . no C13 C14 C15 C16 0.0 . . . . no C14 C15 C16 C17 0.0 . . . . no C15 C16 C17 C18 0.0 . . . . no C16 C17 C18 C13 0.0 . . . . no C14 C13 C18 C17 0.0 . . . . no C12 C13 C18 C17 173.8(9) . . . . no C24 C19 C20 C21 0.0 . . . . no Br2 C19 C20 C21 178.7(4) . . . . no C19 C20 C21 C22 0.0 . . . . no C20 C21 C22 C23 0.0 . . . . no C20 C21 C22 C25 179.1(6) . . . . no O6 C25 C22 C23 -150.9(7) . . . . no C26 C25 C22 C23 29.8(9) . . . . no O6 C25 C22 C21 30.0(9) . . . . no C26 C25 C22 C21 -149.3(6) . . . . no C21 C22 C23 C24 0.0 . . . . no C25 C22 C23 C24 -179.0(6) . . . . no C22 C23 C24 C19 0.0 . . . . no C20 C19 C24 C23 0.0 . . . . no Br2 C19 C24 C23 -178.7(4) . . . . no O6 C25 C26 C27 -12.0(11) . . . . no C22 C25 C26 C27 167.2(6) . . . . no C25 C26 C27 C28 75.9(9) . . . . no C25 C26 C27 C29 -48.6(10) . . . . no C26 C27 C28 N2 169.7(8) . . . . no C29 C27 C28 N2 -65.1(12) . . . . no C28 C27 C29 O10 15.9(13) . . . . no C26 C27 C29 O10 142.2(10) . . . . no C28 C27 C29 O9 -166.4(8) . . . . no C26 C27 C29 O9 -40.1(10) . . . . no O9 C30 C31 C32 81.7(13) . . . . no O9 C30 C31 C36 -97.9(10) . . . . no C36 C31 C32 C33 0.0 . . . . no C30 C31 C32 C33 -179.6(8) . . . . no C31 C32 C33 C34 0.0 . . . . no C32 C33 C34 C35 0.0 . . . . no C33 C34 C35 C36 0.0 . . . . no C34 C35 C36 C31 0.0 . . . . no C32 C31 C36 C35 0.0 . . . . no C30 C31 C36 C35 179.6(8) . . . . no C9 C10 N1 O3 -29.1(13) . . . . no C9 C10 N1 O2 152.2(9) . . . . no C27 C28 N2 O7 -35.1(14) . . . . no C27 C28 N2 O8 147.0(10) . . . . no O5 C11 O4 C12 6.1(15) . . . . no C9 C11 O4 C12 -176.9(10) . . . . no C13 C12 O4 C11 108.5(12) . . . . no O10 C29 O9 C30 -2.4(16) . . . . no C27 C29 O9 C30 179.9(9) . . . . no C31 C30 O9 C29 -104.6(11) . . . . no _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.455 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.067