# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Kei Takeda' _publ_contact_author_email takedak@hiroshima-u.ac.jp _publ_section_title ; Enantioselective Trapping of an a-Chiral Carbanion of Acyclic Nitrile by a Carbon Electrophile ; _publ_author_name K.Takeda # Attachment '- 1102kwh.cif' data_TMT-IV-685B _database_code_depnum_ccdc_archive 'CCDC 860190' #TrackingRef '- 1102kwh.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H15 Br N2 O4' _chemical_formula_weight 355.19 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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.4223(14) _cell_length_b 6.1123(11) _cell_length_c 14.743(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.455(2) _cell_angle_gamma 90.00 _cell_volume 752.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150 _cell_measurement_reflns_used 3076 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 25.86 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.567 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 2.748 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6095 _exptl_absorpt_correction_T_max 0.8101 _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _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 'Bruker SMART 1000 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 8516 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0643 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3402 _reflns_number_gt 2963 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINT _computing_structure_solution SHELXS-97 _computing_structure_refinement SHELXL-97 _computing_molecular_graphics 'ORTEP-3 for Windows' _computing_publication_material SHELXL-97 _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^)+(0.0171P)^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 ? _chemical_absolute_configuration ad _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.004(8) _refine_ls_number_reflns 3402 _refine_ls_number_parameters 196 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0723 _refine_ls_wR_factor_gt 0.0701 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.972 _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 C1 C 0.5898(3) -0.3939(5) -0.41638(18) 0.0203(6) Uani 1 1 d . . . C2 C 0.6709(3) -0.4651(4) -0.32063(18) 0.0181(5) Uani 1 1 d . . . C3 C 0.6907(3) -0.2648(4) -0.25712(18) 0.0215(6) Uani 1 1 d . . . H3A H 0.7440 -0.1456 -0.2871 0.026 Uiso 1 1 calc R . . H3B H 0.5839 -0.2120 -0.2457 0.026 Uiso 1 1 calc R . . C4 C 0.7907(4) -0.3229(5) -0.16571(19) 0.0309(7) Uani 1 1 d . . . H4A H 0.7575 -0.4690 -0.1461 0.037 Uiso 1 1 calc R . . H4B H 0.9047 -0.3324 -0.1752 0.037 Uiso 1 1 calc R . . C5 C 0.7750(3) -0.1606(6) -0.09006(17) 0.0244(6) Uani 1 1 d . . . C6 C 0.6907(3) -0.2191(5) -0.01838(19) 0.0288(7) Uani 1 1 d . . . H6 H 0.6402 -0.3582 -0.0196 0.035 Uiso 1 1 calc R . . C7 C 0.6787(4) -0.0804(5) 0.0542(2) 0.0311(7) Uani 1 1 d . . . H7 H 0.6213 -0.1237 0.1026 0.037 Uiso 1 1 calc R . . C8 C 0.7518(3) 0.1236(5) 0.05563(19) 0.0244(6) Uani 1 1 d . . . C9 C 0.8362(3) 0.1873(5) -0.01486(19) 0.0251(6) Uani 1 1 d . . . H9 H 0.8862 0.3268 -0.0134 0.030 Uiso 1 1 calc R . . C10 C 0.8471(3) 0.0460(5) -0.08732(19) 0.0254(6) Uani 1 1 d . . . H10 H 0.9042 0.0900 -0.1357 0.031 Uiso 1 1 calc R . . C11 C 0.5757(3) -0.6345(4) -0.27970(18) 0.0201(6) Uani 1 1 d . . . C12 C 0.8375(3) -0.7322(4) -0.37586(17) 0.0196(6) Uani 1 1 d . . . C13 C 1.0158(4) -1.0089(5) -0.4203(2) 0.0353(8) Uani 1 1 d . . . H13A H 0.9138 -1.0665 -0.4504 0.053 Uiso 1 1 calc R . . H13B H 1.0646 -1.1155 -0.3754 0.053 Uiso 1 1 calc R . . H13C H 1.0881 -0.9820 -0.4661 0.053 Uiso 1 1 calc R . . C14 C 1.1273(3) -0.6900(7) -0.32618(19) 0.0342(6) Uani 1 1 d . . . H14A H 1.1065 -0.5322 -0.3264 0.051 Uiso 1 1 calc R . . H14B H 1.2210 -0.7194 -0.3574 0.051 Uiso 1 1 calc R . . H14C H 1.1479 -0.7422 -0.2629 0.051 Uiso 1 1 calc R . . N1 N 0.5055(3) -0.7580(4) -0.24269(17) 0.0286(6) Uani 1 1 d . . . N2 N 0.9875(3) -0.8039(4) -0.37383(16) 0.0236(5) Uani 1 1 d . . . O1 O 0.4327(2) -0.3826(4) -0.41697(14) 0.0280(5) Uani 1 1 d . . . O2 O 0.6634(2) -0.3518(4) -0.47739(14) 0.0305(5) Uani 1 1 d . . . O3 O 0.8294(2) -0.5445(3) -0.32673(13) 0.0209(4) Uani 1 1 d . . . O4 O 0.7173(2) -0.8213(3) -0.41510(13) 0.0251(4) Uani 1 1 d . . . Br1 Br 0.73350(3) 0.31640(6) 0.154364(18) 0.03755(10) Uani 1 1 d . . . H1 H 0.400(4) -0.355(7) -0.466(3) 0.046(11) 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 C1 0.0195(14) 0.0226(14) 0.0178(13) 0.0005(11) -0.0017(11) 0.0016(11) C2 0.0133(12) 0.0216(14) 0.0193(13) 0.0007(11) 0.0016(10) 0.0016(11) C3 0.0202(13) 0.0231(14) 0.0206(13) -0.0023(11) 0.0005(11) 0.0017(10) C4 0.0319(17) 0.0313(17) 0.0258(16) -0.0067(13) -0.0095(13) 0.0079(13) C5 0.0216(12) 0.0254(16) 0.0240(12) -0.0037(14) -0.0059(10) 0.0058(15) C6 0.0245(13) 0.024(2) 0.0358(15) -0.0011(13) -0.0024(11) 0.0016(12) C7 0.0274(16) 0.0360(17) 0.0304(16) 0.0035(13) 0.0060(13) -0.0012(13) C8 0.0224(15) 0.0263(16) 0.0234(15) -0.0022(12) -0.0012(12) 0.0068(12) C9 0.0251(15) 0.0222(15) 0.0259(15) -0.0008(12) -0.0046(12) -0.0010(12) C10 0.0253(15) 0.0305(16) 0.0195(14) 0.0008(12) -0.0007(11) 0.0045(12) C11 0.0205(13) 0.0196(17) 0.0191(13) -0.0009(10) -0.0015(10) 0.0045(10) C12 0.0174(12) 0.0237(18) 0.0175(12) -0.0001(10) 0.0020(10) 0.0016(10) C13 0.0285(17) 0.0324(18) 0.047(2) -0.0075(15) 0.0121(14) 0.0040(14) C14 0.0162(12) 0.0382(16) 0.0465(16) -0.003(2) -0.0027(11) -0.0071(19) N1 0.0262(13) 0.0324(14) 0.0270(13) 0.0042(10) 0.0036(10) 0.0008(10) N2 0.0159(11) 0.0258(13) 0.0283(13) -0.0023(10) 0.0006(9) -0.0002(10) O1 0.0185(10) 0.0455(13) 0.0189(11) 0.0058(10) -0.0018(8) 0.0045(9) O2 0.0258(11) 0.0444(13) 0.0218(11) 0.0090(9) 0.0053(9) 0.0017(10) O3 0.0152(10) 0.0230(10) 0.0238(10) -0.0040(8) -0.0001(8) -0.0002(8) O4 0.0185(10) 0.0309(11) 0.0245(10) -0.0058(8) -0.0025(8) -0.0032(9) Br1 0.04702(18) 0.03944(17) 0.02655(15) -0.00978(16) 0.00609(11) 0.00418(19) _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 C1 O2 1.185(3) . ? C1 O1 1.324(3) . ? C1 C2 1.549(4) . ? C2 O3 1.435(3) . ? C2 C11 1.485(4) . ? C2 C3 1.537(4) . ? C3 C4 1.535(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.511(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.394(4) . ? C5 C10 1.400(5) . ? C6 C7 1.380(4) . ? C6 H6 0.9500 . ? C7 C8 1.390(4) . ? C7 H7 0.9500 . ? C8 C9 1.389(4) . ? C8 Br1 1.895(3) . ? C9 C10 1.386(4) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 N1 1.140(3) . ? C12 O4 1.226(3) . ? C12 N2 1.334(3) . ? C12 O3 1.363(3) . ? C13 N2 1.462(4) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 N2 1.466(4) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? O1 H1 0.75(4) . ? 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 O2 C1 O1 127.2(3) . . ? O2 C1 C2 122.7(2) . . ? O1 C1 C2 110.0(2) . . ? O3 C2 C11 110.2(2) . . ? O3 C2 C3 106.2(2) . . ? C11 C2 C3 109.2(2) . . ? O3 C2 C1 110.0(2) . . ? C11 C2 C1 111.7(2) . . ? C3 C2 C1 109.4(2) . . ? C4 C3 C2 110.8(2) . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C5 C4 C3 113.9(2) . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4B 108.8 . . ? C3 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C6 C5 C10 118.1(3) . . ? C6 C5 C4 119.5(3) . . ? C10 C5 C4 122.3(3) . . ? C7 C6 C5 121.8(3) . . ? C7 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? C6 C7 C8 119.1(3) . . ? C6 C7 H7 120.5 . . ? C8 C7 H7 120.5 . . ? C9 C8 C7 120.6(3) . . ? C9 C8 Br1 120.1(2) . . ? C7 C8 Br1 119.3(2) . . ? C10 C9 C8 119.6(3) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C9 C10 C5 120.8(3) . . ? C9 C10 H10 119.6 . . ? C5 C10 H10 119.6 . . ? N1 C11 C2 175.4(3) . . ? O4 C12 N2 125.9(2) . . ? O4 C12 O3 122.0(2) . . ? N2 C12 O3 112.1(2) . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N2 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 N2 C13 118.9(2) . . ? C12 N2 C14 123.6(3) . . ? C13 N2 C14 117.5(3) . . ? C1 O1 H1 105(3) . . ? C12 O3 C2 115.4(2) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.406 _refine_diff_density_min -0.445 _refine_diff_density_rms 0.067 # Attachment '- 1116kwh.cif' data_TMT-IV-714D _database_code_depnum_ccdc_archive 'CCDC 860191' #TrackingRef '- 1116kwh.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H19 Br N2 O3' _chemical_formula_weight 415.28 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 C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 16.499(7) _cell_length_b 6.349(3) _cell_length_c 18.273(8) _cell_angle_alpha 90.00 _cell_angle_beta 98.851(6) _cell_angle_gamma 90.00 _cell_volume 1891.4(15) _cell_formula_units_Z 4 _cell_measurement_temperature 120 _cell_measurement_reflns_used 2242 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 26.45 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 2.195 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.3526 _exptl_absorpt_correction_T_max 0.9574 _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120 _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 'Bruker SMART 1000 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 10342 _diffrn_reflns_av_R_equivalents 0.0767 _diffrn_reflns_av_sigmaI/netI 0.1391 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.13 _diffrn_reflns_theta_max 27.61 _reflns_number_total 4274 _reflns_number_gt 2386 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINT _computing_structure_solution SHELXS-97 _computing_structure_refinement SHELXL-97 _computing_molecular_graphics 'ORTEP-3 for Windows' _computing_publication_material SHELXL-97 _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^)+(0.0692P)^2^+5.1157P] 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 SHELXL _refine_ls_extinction_coef 0.0047(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _chemical_absolute_configuration ad _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(2) _refine_ls_number_reflns 4274 _refine_ls_number_parameters 238 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1310 _refine_ls_R_factor_gt 0.0749 _refine_ls_wR_factor_ref 0.1971 _refine_ls_wR_factor_gt 0.1627 _refine_ls_goodness_of_fit_ref 1.126 _refine_ls_restrained_S_all 1.126 _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 C1 C 0.7683(5) 0.7861(13) 0.2898(4) 0.0248(18) Uani 1 1 d . . . C2 C 0.7873(4) 0.5712(13) 0.2693(3) 0.0205(15) Uani 1 1 d . . . C3 C 0.8346(4) 0.4568(12) 0.3381(4) 0.0234(17) Uani 1 1 d . . . H3A H 0.8505 0.3148 0.3231 0.028 Uiso 1 1 calc R . . H3B H 0.8855 0.5358 0.3558 0.028 Uiso 1 1 calc R . . C4 C 0.7849(4) 0.4349(13) 0.4019(4) 0.0247(17) Uani 1 1 d . . . H4A H 0.7637 0.5747 0.4136 0.030 Uiso 1 1 calc R . . H4B H 0.7374 0.3411 0.3866 0.030 Uiso 1 1 calc R . . C5 C 0.8371(5) 0.3452(12) 0.4706(4) 0.0238(17) Uani 1 1 d . . . C6 C 0.8643(5) 0.1332(12) 0.4712(5) 0.033(2) Uani 1 1 d . . . H6 H 0.8499 0.0474 0.4286 0.039 Uiso 1 1 calc R . . C7 C 0.9118(4) 0.0509(18) 0.5341(4) 0.042(2) Uani 1 1 d . . . H7 H 0.9303 -0.0908 0.5346 0.050 Uiso 1 1 calc R . . C8 C 0.9320(6) 0.1770(16) 0.5959(5) 0.043(2) Uani 1 1 d . . . C9 C 0.9060(6) 0.3842(19) 0.5972(5) 0.047(3) Uani 1 1 d . . . H9 H 0.9211 0.4691 0.6399 0.056 Uiso 1 1 calc R . . C10 C 0.8574(5) 0.4653(15) 0.5347(4) 0.036(2) Uani 1 1 d . . . H10 H 0.8375 0.6055 0.5357 0.043 Uiso 1 1 calc R . . C11 C 0.8419(4) 0.5817(14) 0.2083(4) 0.0262(17) Uani 1 1 d . . . C12 C 0.8380(4) 0.4221(12) 0.1488(4) 0.0228(17) Uani 1 1 d . . . C13 C 0.8073(5) 0.2180(13) 0.1543(4) 0.0266(18) Uani 1 1 d . . . H13 H 0.7905 0.1735 0.1993 0.032 Uiso 1 1 calc R . . C14 C 0.8011(4) 0.0798(15) 0.0948(4) 0.0325(18) Uani 1 1 d . . . H14 H 0.7785 -0.0566 0.0988 0.039 Uiso 1 1 calc R . . C15 C 0.8277(5) 0.1405(12) 0.0294(4) 0.0287(19) Uani 1 1 d . . . H15 H 0.8237 0.0460 -0.0113 0.034 Uiso 1 1 calc R . . C16 C 0.8604(5) 0.3412(13) 0.0241(5) 0.0317(19) Uani 1 1 d . . . H16 H 0.8785 0.3844 -0.0205 0.038 Uiso 1 1 calc R . . C17 C 0.8666(5) 0.4763(12) 0.0831(4) 0.0258(18) Uani 1 1 d . . . H17 H 0.8910 0.6107 0.0794 0.031 Uiso 1 1 calc R . . C18 C 0.6623(4) 0.5214(12) 0.1877(4) 0.0186(15) Uani 1 1 d . . . C19 C 0.5921(5) 0.1834(12) 0.1970(5) 0.0300(19) Uani 1 1 d . . . H19A H 0.6381 0.1588 0.2369 0.045 Uiso 1 1 calc R . . H19B H 0.5925 0.0761 0.1586 0.045 Uiso 1 1 calc R . . H19C H 0.5404 0.1755 0.2171 0.045 Uiso 1 1 calc R . . C20 C 0.5357(5) 0.4564(15) 0.1058(4) 0.038(2) Uani 1 1 d . . . H20A H 0.4830 0.4588 0.1242 0.057 Uiso 1 1 calc R . . H20B H 0.5329 0.3566 0.0646 0.057 Uiso 1 1 calc R . . H20C H 0.5480 0.5974 0.0887 0.057 Uiso 1 1 calc R . . N1 N 0.7547(4) 0.9496(11) 0.3106(4) 0.0298(16) Uani 1 1 d . . . N2 N 0.6002(4) 0.3914(10) 0.1652(3) 0.0260(15) Uani 1 1 d . . . O1 O 0.7132(3) 0.4487(8) 0.2488(3) 0.0235(12) Uani 1 1 d . . . O2 O 0.6759(3) 0.6912(8) 0.1582(3) 0.0282(13) Uani 1 1 d . . . O3 O 0.8883(3) 0.7305(8) 0.2112(3) 0.0260(13) Uani 1 1 d . . . Br1 Br 0.99601(6) 0.0547(2) 0.68054(6) 0.0709(5) 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 C1 0.026(4) 0.025(5) 0.023(4) 0.005(3) 0.003(3) 0.006(4) C2 0.019(3) 0.020(4) 0.022(3) -0.003(4) 0.002(3) -0.003(4) C3 0.019(4) 0.029(4) 0.022(4) 0.000(3) 0.003(3) 0.006(3) C4 0.025(4) 0.031(4) 0.018(4) 0.003(3) 0.002(3) 0.001(3) C5 0.026(4) 0.035(5) 0.012(4) 0.004(3) 0.006(3) -0.004(3) C6 0.025(4) 0.032(5) 0.040(5) 0.003(4) -0.001(4) 0.006(4) C7 0.022(4) 0.049(6) 0.051(5) 0.018(6) -0.004(4) -0.013(5) C8 0.038(5) 0.059(7) 0.035(5) -0.003(5) 0.015(4) -0.023(5) C9 0.037(5) 0.088(8) 0.015(4) -0.008(5) 0.006(4) -0.004(5) C10 0.038(5) 0.050(6) 0.019(4) 0.001(4) 0.004(4) 0.002(4) C11 0.024(4) 0.030(4) 0.023(4) -0.005(4) 0.001(3) 0.007(4) C12 0.021(4) 0.031(4) 0.015(4) -0.001(3) 0.000(3) -0.002(3) C13 0.025(4) 0.030(4) 0.025(4) 0.008(4) 0.004(3) 0.003(4) C14 0.034(4) 0.029(4) 0.033(4) -0.007(4) 0.001(3) -0.002(4) C15 0.036(5) 0.031(5) 0.020(4) -0.006(3) 0.003(3) 0.003(4) C16 0.034(5) 0.032(5) 0.029(5) 0.004(4) 0.006(4) 0.001(4) C17 0.031(4) 0.028(5) 0.019(4) -0.003(3) 0.005(3) -0.003(3) C18 0.015(3) 0.021(4) 0.019(4) 0.006(3) -0.001(3) -0.006(3) C19 0.031(5) 0.021(4) 0.036(5) 0.007(4) 0.000(4) -0.014(4) C20 0.027(4) 0.054(6) 0.030(5) 0.003(4) -0.005(4) -0.010(4) N1 0.027(4) 0.035(4) 0.026(4) -0.001(3) -0.001(3) -0.002(3) N2 0.025(4) 0.026(4) 0.026(4) 0.004(3) -0.001(3) -0.004(3) O1 0.021(3) 0.026(3) 0.023(3) 0.001(2) 0.000(2) 0.000(2) O2 0.030(3) 0.028(3) 0.025(3) 0.007(2) 0.001(2) -0.001(3) O3 0.027(3) 0.026(3) 0.024(3) -0.008(2) 0.003(2) -0.012(3) Br1 0.0389(5) 0.1210(11) 0.0465(6) 0.0512(7) -0.0130(4) -0.0308(7) _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 C1 N1 1.140(9) . ? C1 C2 1.461(12) . ? C2 O1 1.449(8) . ? C2 C11 1.540(9) . ? C2 C3 1.554(10) . ? C3 C4 1.531(10) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.520(10) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C10 1.394(11) . ? C5 C6 1.418(10) . ? C6 C7 1.389(11) . ? C6 H6 0.9500 . ? C7 C8 1.383(13) . ? C7 H7 0.9500 . ? C8 C9 1.385(15) . ? C8 Br1 1.900(10) . ? C9 C10 1.389(12) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 O3 1.212(9) . ? C11 C12 1.480(10) . ? C12 C17 1.398(10) . ? C12 C13 1.401(11) . ? C13 C14 1.389(11) . ? C13 H13 0.9500 . ? C14 C15 1.390(11) . ? C14 H14 0.9500 . ? C15 C16 1.393(11) . ? C15 H15 0.9500 . ? C16 C17 1.370(11) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 O2 1.241(9) . ? C18 N2 1.331(9) . ? C18 O1 1.370(8) . ? C19 N2 1.457(9) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 N2 1.458(10) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 175.4(8) . . ? O1 C2 C1 111.3(6) . . ? O1 C2 C11 113.6(5) . . ? C1 C2 C11 108.5(6) . . ? O1 C2 C3 104.9(6) . . ? C1 C2 C3 109.2(6) . . ? C11 C2 C3 109.2(5) . . ? C4 C3 C2 113.4(6) . . ? C4 C3 H3A 108.9 . . ? C2 C3 H3A 108.9 . . ? C4 C3 H3B 108.9 . . ? C2 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C5 C4 C3 111.2(6) . . ? C5 C4 H4A 109.4 . . ? C3 C4 H4A 109.4 . . ? C5 C4 H4B 109.4 . . ? C3 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C10 C5 C6 118.6(7) . . ? C10 C5 C4 121.4(7) . . ? C6 C5 C4 120.0(7) . . ? C7 C6 C5 120.0(8) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C8 C7 C6 119.5(10) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C7 C8 C9 121.8(9) . . ? C7 C8 Br1 117.5(8) . . ? C9 C8 Br1 120.6(7) . . ? C8 C9 C10 118.6(9) . . ? C8 C9 H9 120.7 . . ? C10 C9 H9 120.7 . . ? C9 C10 C5 121.4(9) . . ? C9 C10 H10 119.3 . . ? C5 C10 H10 119.3 . . ? O3 C11 C12 121.5(7) . . ? O3 C11 C2 116.0(7) . . ? C12 C11 C2 122.5(7) . . ? C17 C12 C13 117.6(7) . . ? C17 C12 C11 118.6(7) . . ? C13 C12 C11 123.8(7) . . ? C14 C13 C12 120.8(7) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 120.2(8) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C14 C15 C16 119.4(7) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C17 C16 C15 120.1(7) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C12 121.8(7) . . ? C16 C17 H17 119.1 . . ? C12 C17 H17 119.1 . . ? O2 C18 N2 126.0(7) . . ? O2 C18 O1 121.2(6) . . ? N2 C18 O1 112.8(6) . . ? N2 C19 H19A 109.5 . . ? N2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N2 C20 H20A 109.5 . . ? N2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 N2 C19 123.5(6) . . ? C18 N2 C20 119.5(6) . . ? C19 N2 C20 117.0(7) . . ? C18 O1 C2 114.7(5) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.602 _refine_diff_density_min -1.211 _refine_diff_density_rms 0.137