# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Ma, Jun-An' _publ_contact_author_email 'majun an68@tju.edu.cn' _publ_section_title ; A Powerful Synergistic Effect for Highly Efficient Diastereo- and Enantioselective Phase-Transfer Catalyzed Conjugate Additions ; loop_ _publ_author_name 'Jun-An Ma' 'Ming-Qing Hua' 'Lian Wang' 'Han-Feng Cui' 'Jing Nie' 'Xiao-Ling Zhang' # Attachment '- 090726C.cif' data_090726c _database_code_depnum_ccdc_archive 'CCDC 742621' #TrackingRef '- 090726C.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 Br N2 O2' _chemical_formula_weight 400.29 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 18.2314(8) _cell_length_b 7.6297(3) _cell_length_c 18.9377(8) _cell_angle_alpha 90.00 _cell_angle_beta 112.7450(10) _cell_angle_gamma 90.00 _cell_volume 2429.38(18) _cell_formula_units_Z 5 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1025 _exptl_absorpt_coefficient_mu 2.129 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12488 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0781 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 25.03 _reflns_number_total 8232 _reflns_number_gt 6285 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1054P)^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 mixed _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 0.015(11) _refine_ls_number_reflns 8232 _refine_ls_number_parameters 599 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0742 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1829 _refine_ls_wR_factor_gt 0.1670 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 1.672 _refine_ls_shift/su_mean 0.035 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 0.92554(4) 0.34777(12) 0.97690(4) 0.0711(3) Uani 1 1 d . . . Br2 Br 0.19159(5) 0.15968(12) 0.22277(5) 0.0790(3) Uani 1 1 d . . . O1 O 0.6043(3) -0.0096(6) 0.9597(3) 0.0527(11) Uani 1 1 d . . . O2 O 0.7375(3) 0.0600(7) 0.8951(3) 0.0608(12) Uani 1 1 d . . . O3 O 0.8106(2) 0.0042(6) 1.0168(2) 0.0488(10) Uani 1 1 d . . . O4 O 0.2207(3) 0.3792(9) 0.7927(4) 0.0880(18) Uani 1 1 d . . . O5 O 0.2234(3) 0.2158(11) 0.7024(4) 0.100(2) Uani 1 1 d . . . O6 O 0.2034(3) 0.7084(6) 0.4801(3) 0.0697(15) Uani 1 1 d . . . O7 O 0.2955(3) 0.5341(8) 0.3726(3) 0.0747(16) Uani 1 1 d . . . O8 O 0.1699(3) 0.5723(6) 0.2931(2) 0.0570(12) Uani 1 1 d . . . O9 O 0.4523(3) 0.6896(8) 0.8753(3) 0.0729(14) Uani 1 1 d . . . H9 H 0.4743 0.6706 0.8456 0.109 Uiso 1 1 calc R . . O10 O 0.3426(3) 0.8092(9) 0.8679(3) 0.0768(16) Uani 1 1 d . . . H10 H 0.2957 0.7817 0.8460 0.115 Uiso 1 1 calc R . . N1 N 0.6371(2) 0.2682(6) 0.9443(3) 0.0350(10) Uani 1 1 d . . . N2 N 0.2541(3) 0.2830(9) 0.7655(4) 0.0632(17) Uani 1 1 d . . . N3 N 0.2392(3) 0.4280(6) 0.4860(3) 0.0372(11) Uani 1 1 d . . . N4 N 0.3827(3) 0.7300(7) 0.8389(3) 0.0491(12) Uani 1 1 d . . . C1 C 0.9115(3) 0.4332(8) 1.0659(4) 0.0448(14) Uani 1 1 d . . . C2 C 0.9796(4) 0.4786(10) 1.1284(4) 0.0611(18) Uani 1 1 d . . . H2 H 1.0293 0.4700 1.1256 0.073 Uiso 1 1 calc R . . C3 C 0.9733(5) 0.5347(11) 1.1928(5) 0.073(2) Uani 1 1 d . . . H3 H 1.0188 0.5678 1.2343 0.088 Uiso 1 1 calc R . . C4 C 0.8992(4) 0.5439(13) 1.1983(5) 0.079(2) Uani 1 1 d . . . H4 H 0.8953 0.5785 1.2438 0.095 Uiso 1 1 calc R . . C5 C 0.8316(4) 0.5008(10) 1.1353(4) 0.0596(18) Uani 1 1 d . . . H5 H 0.7822 0.5087 1.1387 0.072 Uiso 1 1 calc R . . C6 C 0.8359(3) 0.4453(8) 1.0660(3) 0.0413(13) Uani 1 1 d . . . C7 C 0.7599(3) 0.4126(7) 0.9955(3) 0.0357(12) Uani 1 1 d . . . H7 H 0.7727 0.4231 0.9500 0.043 Uiso 1 1 calc R . . C8 C 0.7214(3) 0.2330(7) 0.9933(3) 0.0316(11) Uani 1 1 d . . . H8 H 0.7260 0.2004 1.0449 0.038 Uiso 1 1 calc R . . C9 C 0.6205(3) 0.4556(7) 0.9231(3) 0.0372(12) Uani 1 1 d . . . H9A H 0.5715 0.4909 0.9290 0.045 Uiso 1 1 calc R . . C10 C 0.6928(3) 0.5401(7) 0.9872(3) 0.0405(13) Uani 1 1 d . . . H10A H 0.7039 0.6557 0.9724 0.049 Uiso 1 1 calc R . . H10B H 0.6842 0.5494 1.0345 0.049 Uiso 1 1 calc R . . C11 C 0.7551(3) 0.0906(7) 0.9607(3) 0.0375(12) Uani 1 1 d . . . C12 C 0.8565(4) -0.1251(10) 0.9930(5) 0.069(2) Uani 1 1 d . . . H12A H 0.8207 -0.2019 0.9552 0.104 Uiso 1 1 calc R . . H12B H 0.8893 -0.1924 1.0367 0.104 Uiso 1 1 calc R . . H12C H 0.8895 -0.0653 0.9717 0.104 Uiso 1 1 calc R . . C13 C 0.5826(3) 0.1384(8) 0.9340(3) 0.0398(13) Uani 1 1 d . . . C14 C 0.4981(3) 0.1803(7) 0.8902(3) 0.0376(12) Uani 1 1 d . . . C15 C 0.4624(4) 0.1255(9) 0.8147(3) 0.0486(15) Uani 1 1 d . . . H15 H 0.4922 0.0675 0.7917 0.058 Uiso 1 1 calc R . . C16 C 0.3814(4) 0.1579(10) 0.7734(4) 0.0530(15) Uani 1 1 d . . . H16 H 0.3566 0.1211 0.7228 0.064 Uiso 1 1 calc R . . C17 C 0.3391(3) 0.2453(8) 0.8089(3) 0.0437(14) Uani 1 1 d . . . C18 C 0.3725(4) 0.2977(8) 0.8837(4) 0.0476(15) Uani 1 1 d . . . H18 H 0.3422 0.3543 0.9066 0.057 Uiso 1 1 calc R . . C19 C 0.4545(3) 0.2637(8) 0.9254(3) 0.0433(14) Uani 1 1 d . . . H19 H 0.4787 0.2977 0.9764 0.052 Uiso 1 1 calc R . . C20 C 0.6144(3) 0.5007(8) 0.8428(3) 0.0419(13) Uani 1 1 d . . . C21 C 0.6125(3) 0.3778(9) 0.7895(3) 0.0495(15) Uani 1 1 d . . . H21 H 0.6159 0.2595 0.8022 0.059 Uiso 1 1 calc R . . C22 C 0.6055(5) 0.4278(11) 0.7164(4) 0.0649(19) Uani 1 1 d . . . H22 H 0.6050 0.3439 0.6806 0.078 Uiso 1 1 calc R . . C23 C 0.5992(4) 0.6048(13) 0.6977(5) 0.077(3) Uani 1 1 d . . . H23 H 0.5926 0.6394 0.6485 0.092 Uiso 1 1 calc R . . C24 C 0.6027(4) 0.7279(11) 0.7509(4) 0.0647(19) Uani 1 1 d . . . H24 H 0.6004 0.8462 0.7384 0.078 Uiso 1 1 calc R . . C25 C 0.6097(4) 0.6783(9) 0.8234(4) 0.0537(16) Uani 1 1 d . . . H25 H 0.6113 0.7631 0.8592 0.064 Uiso 1 1 calc R . . C26 C 0.1006(4) 0.1274(9) 0.2484(4) 0.0537(16) Uani 1 1 d . . . C27 C 0.0315(5) 0.0740(10) 0.1911(4) 0.0656(19) Uani 1 1 d . . . H27 H 0.0306 0.0491 0.1427 0.079 Uiso 1 1 calc R . . C28 C -0.0367(5) 0.0572(12) 0.2056(5) 0.081(3) Uani 1 1 d . . . H28 H -0.0838 0.0231 0.1664 0.097 Uiso 1 1 calc R . . C29 C -0.0357(4) 0.0898(15) 0.2760(5) 0.084(3) Uani 1 1 d . . . H29 H -0.0817 0.0760 0.2856 0.101 Uiso 1 1 calc R . . C30 C 0.0347(4) 0.1442(13) 0.3341(4) 0.072(2) Uani 1 1 d . . . H30 H 0.0350 0.1692 0.3823 0.086 Uiso 1 1 calc R . . C31 C 0.1057(3) 0.1624(9) 0.3214(4) 0.0473(14) Uani 1 1 d . . . C32 C 0.1836(3) 0.2155(8) 0.3880(3) 0.0441(14) Uani 1 1 d . . . H32 H 0.2288 0.1783 0.3758 0.053 Uiso 1 1 calc R . . C33 C 0.1900(3) 0.4139(8) 0.4036(3) 0.0389(13) Uani 1 1 d . . . H33 H 0.1370 0.4615 0.3935 0.047 Uiso 1 1 calc R . . C34 C 0.2573(3) 0.2528(7) 0.5234(3) 0.0368(12) Uani 1 1 d . . . H34 H 0.2490 0.2572 0.5715 0.044 Uiso 1 1 calc R . . C35 C 0.1938(4) 0.1397(8) 0.4671(4) 0.0468(14) Uani 1 1 d . . . H35A H 0.1446 0.1477 0.4753 0.056 Uiso 1 1 calc R . . H35B H 0.2105 0.0181 0.4716 0.056 Uiso 1 1 calc R . . C36 C 0.2269(4) 0.5128(8) 0.3564(3) 0.0460(14) Uani 1 1 d . . . C37 C 0.1986(5) 0.6643(15) 0.2409(4) 0.087(3) Uani 1 1 d . . . H37A H 0.2337 0.7573 0.2679 0.131 Uiso 1 1 calc R . . H37B H 0.1543 0.7123 0.1990 0.131 Uiso 1 1 calc R . . H37C H 0.2268 0.5836 0.2215 0.131 Uiso 1 1 calc R . . C38 C 0.2369(4) 0.5831(8) 0.5202(4) 0.0457(14) Uani 1 1 d . . . C39 C 0.2755(3) 0.6039(7) 0.6046(3) 0.0423(14) Uani 1 1 d . . . C40 C 0.2327(4) 0.6906(10) 0.6398(4) 0.0571(17) Uani 1 1 d . . . H40 H 0.1801 0.7222 0.6117 0.069 Uiso 1 1 calc R . . C41 C 0.2672(4) 0.7307(10) 0.7162(4) 0.0570(17) Uani 1 1 d . . . H41 H 0.2380 0.7879 0.7402 0.068 Uiso 1 1 calc R . . C42 C 0.3461(3) 0.6852(8) 0.7576(3) 0.0435(14) Uani 1 1 d . . . C43 C 0.3899(4) 0.6017(8) 0.7239(4) 0.0464(15) Uani 1 1 d . . . H43 H 0.4429 0.5737 0.7522 0.056 Uiso 1 1 calc R . . C44 C 0.3548(4) 0.5589(8) 0.6470(3) 0.0475(14) Uani 1 1 d . . . H44 H 0.3841 0.5001 0.6236 0.057 Uiso 1 1 calc R . . C45 C 0.3414(3) 0.1887(7) 0.5399(3) 0.0358(12) Uani 1 1 d . . . C46 C 0.3640(4) 0.0323(8) 0.5801(4) 0.0479(15) Uani 1 1 d . . . H46 H 0.3277 -0.0286 0.5944 0.058 Uiso 1 1 calc R . . C47 C 0.4400(4) -0.0336(9) 0.5992(4) 0.0611(18) Uani 1 1 d . . . H47 H 0.4542 -0.1394 0.6253 0.073 Uiso 1 1 calc R . . C48 C 0.4941(4) 0.0561(10) 0.5797(4) 0.0558(17) Uani 1 1 d . . . H48 H 0.5456 0.0136 0.5940 0.067 Uiso 1 1 calc R . . C49 C 0.4722(4) 0.2092(9) 0.5390(3) 0.0510(16) Uani 1 1 d . . . H49 H 0.5086 0.2694 0.5246 0.061 Uiso 1 1 calc R . . C50 C 0.3951(4) 0.2748(8) 0.5190(3) 0.0453(14) Uani 1 1 d . . . H50 H 0.3805 0.3784 0.4912 0.054 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0469(4) 0.1012(6) 0.0758(5) 0.0020(4) 0.0354(3) -0.0017(4) Br2 0.0749(5) 0.0964(6) 0.0753(5) -0.0188(5) 0.0395(4) -0.0039(5) O1 0.048(2) 0.041(2) 0.065(3) 0.012(2) 0.017(2) -0.002(2) O2 0.062(3) 0.071(3) 0.048(3) -0.006(2) 0.019(2) 0.018(2) O3 0.043(2) 0.044(2) 0.056(2) 0.005(2) 0.016(2) 0.0133(19) O4 0.043(3) 0.094(5) 0.116(5) 0.018(4) 0.019(3) 0.016(3) O5 0.047(3) 0.148(6) 0.073(4) 0.016(4) -0.013(3) -0.012(4) O6 0.091(4) 0.035(2) 0.055(3) 0.006(2) -0.003(3) 0.011(2) O7 0.033(2) 0.118(4) 0.065(3) 0.037(3) 0.011(2) -0.009(3) O8 0.048(2) 0.066(3) 0.049(2) 0.018(2) 0.009(2) -0.009(2) O9 0.072(4) 0.085(4) 0.049(3) -0.009(3) 0.010(3) 0.009(3) O10 0.074(3) 0.107(5) 0.055(3) -0.008(3) 0.032(3) 0.004(3) N1 0.024(2) 0.038(3) 0.039(2) 0.0041(19) 0.0082(19) 0.0001(19) N2 0.035(3) 0.074(4) 0.070(4) 0.024(3) 0.010(3) -0.003(3) N3 0.034(2) 0.036(3) 0.034(2) 0.007(2) 0.006(2) 0.001(2) N4 0.057(3) 0.045(3) 0.046(3) -0.002(2) 0.021(3) -0.009(3) C1 0.030(3) 0.042(3) 0.058(4) 0.011(3) 0.013(3) 0.002(2) C2 0.036(3) 0.060(4) 0.071(5) 0.008(4) 0.002(3) 0.001(3) C3 0.051(4) 0.071(5) 0.070(5) -0.012(4) -0.007(4) 0.001(4) C4 0.055(5) 0.097(6) 0.063(5) -0.023(5) -0.002(4) 0.010(4) C5 0.039(3) 0.080(5) 0.051(4) -0.019(4) 0.008(3) 0.006(3) C6 0.032(3) 0.035(3) 0.046(3) 0.001(3) 0.003(2) 0.001(2) C7 0.027(3) 0.038(3) 0.038(3) 0.002(2) 0.007(2) 0.003(2) C8 0.026(3) 0.033(3) 0.031(3) 0.000(2) 0.007(2) 0.001(2) C9 0.037(3) 0.033(3) 0.040(3) 0.004(2) 0.012(2) 0.003(2) C10 0.031(3) 0.034(3) 0.051(3) -0.001(3) 0.009(3) 0.001(2) C11 0.033(3) 0.038(3) 0.039(3) 0.002(2) 0.012(3) 0.004(2) C12 0.061(4) 0.048(4) 0.112(6) 0.002(4) 0.048(4) 0.018(4) C13 0.041(3) 0.044(3) 0.037(3) 0.001(3) 0.018(2) -0.001(3) C14 0.028(3) 0.035(3) 0.046(3) 0.000(3) 0.011(2) -0.006(2) C15 0.044(3) 0.058(4) 0.047(3) -0.007(3) 0.022(3) -0.008(3) C16 0.047(4) 0.057(4) 0.044(3) 0.000(3) 0.005(3) -0.012(3) C17 0.029(3) 0.049(3) 0.045(3) 0.011(3) 0.006(3) -0.008(3) C18 0.042(3) 0.044(4) 0.060(4) 0.004(3) 0.022(3) -0.002(3) C19 0.038(3) 0.051(3) 0.040(3) -0.004(3) 0.014(3) -0.007(3) C20 0.027(3) 0.046(3) 0.045(3) 0.006(3) 0.005(2) 0.004(2) C21 0.045(3) 0.056(4) 0.039(3) 0.007(3) 0.007(3) 0.002(3) C22 0.069(5) 0.074(5) 0.044(4) 0.000(4) 0.013(3) 0.004(4) C23 0.054(4) 0.104(7) 0.060(5) 0.044(5) 0.009(4) 0.010(4) C24 0.063(4) 0.060(4) 0.063(4) 0.022(4) 0.016(4) 0.005(4) C25 0.049(4) 0.049(4) 0.056(4) 0.013(3) 0.012(3) 0.007(3) C26 0.049(4) 0.052(4) 0.052(4) -0.010(3) 0.011(3) 0.002(3) C27 0.063(5) 0.062(4) 0.059(4) -0.014(4) 0.010(4) 0.000(4) C28 0.055(5) 0.074(5) 0.079(6) -0.014(5) -0.011(4) -0.010(4) C29 0.041(4) 0.125(8) 0.077(5) -0.011(5) 0.012(4) -0.021(4) C30 0.046(4) 0.101(6) 0.059(4) -0.006(4) 0.010(3) -0.013(4) C31 0.037(3) 0.044(3) 0.055(4) -0.005(3) 0.011(3) -0.004(3) C32 0.036(3) 0.049(4) 0.042(3) 0.000(3) 0.009(3) 0.000(3) C33 0.033(3) 0.041(3) 0.040(3) 0.008(2) 0.010(2) -0.001(2) C34 0.043(3) 0.028(3) 0.039(3) 0.005(2) 0.015(3) 0.003(2) C35 0.040(3) 0.037(3) 0.059(3) 0.002(3) 0.014(3) -0.005(3) C36 0.042(3) 0.046(4) 0.040(3) 0.007(3) 0.005(3) -0.004(3) C37 0.089(6) 0.110(7) 0.058(4) 0.043(5) 0.023(4) -0.010(5) C38 0.048(4) 0.033(3) 0.050(3) 0.003(3) 0.012(3) -0.002(3) C39 0.042(3) 0.031(3) 0.044(3) -0.001(2) 0.007(3) -0.005(2) C40 0.040(3) 0.062(4) 0.057(4) -0.003(3) 0.005(3) 0.006(3) C41 0.052(4) 0.059(4) 0.064(4) -0.011(3) 0.027(3) 0.002(3) C42 0.049(3) 0.042(3) 0.038(3) -0.004(3) 0.014(3) -0.003(3) C43 0.040(3) 0.045(4) 0.048(3) 0.000(3) 0.010(3) -0.001(3) C44 0.049(4) 0.044(3) 0.046(3) -0.001(3) 0.014(3) 0.001(3) C45 0.035(3) 0.036(3) 0.031(3) 0.001(2) 0.006(2) 0.004(2) C46 0.040(3) 0.044(4) 0.059(4) 0.012(3) 0.018(3) 0.004(3) C47 0.065(4) 0.041(4) 0.071(5) 0.011(3) 0.019(4) 0.013(3) C48 0.044(4) 0.065(4) 0.058(4) -0.007(3) 0.019(3) 0.011(3) C49 0.045(3) 0.061(4) 0.049(3) 0.002(3) 0.020(3) -0.003(3) C50 0.043(3) 0.051(4) 0.036(3) 0.007(3) 0.010(3) 0.001(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 C1 1.914(7) . ? Br2 C26 1.917(7) . ? O1 C13 1.232(8) . ? O2 C11 1.179(7) . ? O3 C11 1.325(7) . ? O3 C12 1.473(8) . ? O4 N2 1.190(9) . ? O5 N2 1.221(9) . ? O6 C38 1.226(7) . ? O7 C36 1.178(7) . ? O8 C36 1.326(7) . ? O8 C37 1.463(8) . ? O9 N4 1.226(7) . ? O10 N4 1.229(7) . ? N1 C13 1.362(7) . ? N1 C8 1.481(6) . ? N1 C9 1.484(7) . ? N2 C17 1.474(8) . ? N3 C38 1.357(8) . ? N3 C33 1.473(7) . ? N3 C34 1.488(7) . ? N4 C42 1.462(8) . ? C1 C6 1.383(8) . ? C1 C2 1.388(9) . ? C2 C3 1.338(11) . ? C3 C4 1.397(12) . ? C4 C5 1.383(9) . ? C5 C6 1.409(9) . ? C6 C7 1.527(7) . ? C7 C10 1.523(8) . ? C7 C8 1.532(8) . ? C8 C11 1.494(8) . ? C9 C20 1.521(8) . ? C9 C10 1.546(8) . ? C13 C14 1.476(8) . ? C14 C19 1.374(8) . ? C14 C15 1.387(8) . ? C15 C16 1.401(9) . ? C16 C17 1.376(9) . ? C17 C18 1.368(9) . ? C18 C19 1.420(8) . ? C20 C21 1.368(9) . ? C20 C25 1.398(9) . ? C21 C22 1.395(9) . ? C22 C23 1.389(13) . ? C23 C24 1.360(12) . ? C24 C25 1.381(10) . ? C26 C27 1.368(9) . ? C26 C31 1.374(9) . ? C27 C28 1.379(12) . ? C28 C29 1.350(13) . ? C29 C30 1.393(11) . ? C30 C31 1.412(9) . ? C31 C32 1.545(8) . ? C32 C33 1.538(9) . ? C32 C35 1.549(9) . ? C33 C36 1.512(8) . ? C34 C35 1.504(8) . ? C34 C45 1.523(8) . ? C38 C39 1.485(9) . ? C39 C40 1.377(9) . ? C39 C44 1.399(9) . ? C40 C41 1.371(10) . ? C41 C42 1.390(9) . ? C42 C43 1.359(8) . ? C43 C44 1.384(9) . ? C45 C50 1.359(8) . ? C45 C46 1.389(8) . ? C46 C47 1.384(9) . ? C47 C48 1.363(10) . ? C48 C49 1.371(10) . ? C49 C50 1.400(9) . ? 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 C11 O3 C12 115.8(5) . . ? C36 O8 C37 114.5(5) . . ? C13 N1 C8 118.7(4) . . ? C13 N1 C9 126.9(5) . . ? C8 N1 C9 113.4(4) . . ? O4 N2 O5 124.4(7) . . ? O4 N2 C17 118.9(7) . . ? O5 N2 C17 116.7(7) . . ? C38 N3 C33 116.8(5) . . ? C38 N3 C34 126.8(4) . . ? C33 N3 C34 111.7(4) . . ? O9 N4 O10 122.5(5) . . ? O9 N4 C42 119.0(5) . . ? O10 N4 C42 118.4(5) . . ? C6 C1 C2 123.0(6) . . ? C6 C1 Br1 119.8(4) . . ? C2 C1 Br1 117.2(5) . . ? C3 C2 C1 119.6(7) . . ? C2 C3 C4 120.7(7) . . ? C5 C4 C3 119.2(7) . . ? C4 C5 C6 121.5(6) . . ? C1 C6 C5 115.9(5) . . ? C1 C6 C7 123.7(5) . . ? C5 C6 C7 120.3(5) . . ? C10 C7 C6 114.0(5) . . ? C10 C7 C8 103.1(4) . . ? C6 C7 C8 114.9(4) . . ? N1 C8 C11 111.5(4) . . ? N1 C8 C7 102.0(4) . . ? C11 C8 C7 113.9(4) . . ? N1 C9 C20 114.6(5) . . ? N1 C9 C10 99.6(4) . . ? C20 C9 C10 113.6(5) . . ? C7 C10 C9 102.8(4) . . ? O2 C11 O3 124.0(5) . . ? O2 C11 C8 126.2(5) . . ? O3 C11 C8 109.8(5) . . ? O1 C13 N1 120.3(5) . . ? O1 C13 C14 121.7(5) . . ? N1 C13 C14 117.9(5) . . ? C19 C14 C15 120.8(5) . . ? C19 C14 C13 120.1(5) . . ? C15 C14 C13 119.0(5) . . ? C14 C15 C16 119.7(6) . . ? C17 C16 C15 118.8(6) . . ? C18 C17 C16 122.6(5) . . ? C18 C17 N2 118.1(6) . . ? C16 C17 N2 119.3(6) . . ? C17 C18 C19 118.3(6) . . ? C14 C19 C18 119.8(5) . . ? C21 C20 C25 119.2(6) . . ? C21 C20 C9 123.6(5) . . ? C25 C20 C9 117.1(6) . . ? C20 C21 C22 120.8(7) . . ? C23 C22 C21 119.0(8) . . ? C24 C23 C22 120.5(7) . . ? C23 C24 C25 120.4(7) . . ? C24 C25 C20 120.0(7) . . ? C27 C26 C31 122.7(7) . . ? C27 C26 Br2 117.2(5) . . ? C31 C26 Br2 120.0(5) . . ? C26 C27 C28 119.5(7) . . ? C29 C28 C27 120.8(7) . . ? C28 C29 C30 119.4(8) . . ? C29 C30 C31 121.4(7) . . ? C26 C31 C30 116.2(6) . . ? C26 C31 C32 123.8(5) . . ? C30 C31 C32 120.0(6) . . ? C33 C32 C31 113.1(5) . . ? C33 C32 C35 102.1(5) . . ? C31 C32 C35 114.9(5) . . ? N3 C33 C36 111.3(5) . . ? N3 C33 C32 104.2(4) . . ? C36 C33 C32 113.3(5) . . ? N3 C34 C35 102.1(4) . . ? N3 C34 C45 114.0(5) . . ? C35 C34 C45 113.5(5) . . ? C34 C35 C32 104.1(5) . . ? O7 C36 O8 124.8(6) . . ? O7 C36 C33 125.7(5) . . ? O8 C36 C33 109.5(5) . . ? O6 C38 N3 119.0(5) . . ? O6 C38 C39 119.9(5) . . ? N3 C38 C39 121.1(5) . . ? C40 C39 C44 119.6(6) . . ? C40 C39 C38 116.8(5) . . ? C44 C39 C38 123.1(6) . . ? C39 C40 C41 120.3(6) . . ? C40 C41 C42 119.5(6) . . ? C43 C42 C41 121.4(5) . . ? C43 C42 N4 119.4(5) . . ? C41 C42 N4 119.2(5) . . ? C42 C43 C44 119.2(6) . . ? C43 C44 C39 120.1(6) . . ? C50 C45 C46 118.8(5) . . ? C50 C45 C34 124.5(5) . . ? C46 C45 C34 116.7(5) . . ? C47 C46 C45 120.6(6) . . ? C48 C47 C46 120.2(6) . . ? C47 C48 C49 119.8(6) . . ? C48 C49 C50 120.0(6) . . ? C45 C50 C49 120.6(6) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.262 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.145