# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Michael Shipman' 'Paul J. Dransfield' 'Paul M. Gore' 'Ivan Prokes' 'Alexandra M. Z. Slawin' _publ_contact_author_name 'Dr Michael Shipman' _publ_contact_author_address ; School of Chemistry University of Exeter Stocker Road Exeter Devon EX4 4UU UNITED KINGDOM ; _publ_contact_author_email M.SHIPMAN@EXETER.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Preparation and Reactivity of Imino Glycals: Stereocontrolled, Divergent Approach to Imino Sugars ; data_16 _database_code_CSD 208078 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H15 Br N O4.Cl' _chemical_formula_sum 'C10 H15 Br Cl N O4' _chemical_formula_weight 328.59 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' Cl Cl 0.1484 0.1585 '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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.9448(5) _cell_length_b 20.8400(15) _cell_length_c 30.325(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4388.9(5) _cell_formula_units_Z 12 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 140 _cell_measurement_theta_min 12 _cell_measurement_theta_max 168 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .1 _exptl_crystal_size_mid .05 _exptl_crystal_size_min .05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1992 _exptl_absorpt_coefficient_mu 2.994 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.780642 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 0.9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22127 _diffrn_reflns_av_R_equivalents 0.0656 _diffrn_reflns_av_sigmaI/netI 0.1022 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 23.26 _reflns_number_total 6249 _reflns_number_gt 3699 _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^)+(0.0272P)^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 SHELXL _refine_ls_extinction_coef 0.00026(8) _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 -0.002(8) _refine_ls_number_reflns 6249 _refine_ls_number_parameters 485 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0810 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0606 _refine_ls_wR_factor_gt 0.0530 _refine_ls_goodness_of_fit_ref 0.733 _refine_ls_restrained_S_all 0.732 _refine_ls_shift/su_max 0.120 _refine_ls_shift/su_mean 0.008 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 Cl1 Cl 0.04949(18) 0.63395(7) 1.14973(5) 0.0683(5) Uani 1 1 d . . . N1 N -0.0137(7) 0.7707(2) 1.11543(13) 0.0437(10) Uani 1 1 d D . . H1A H 0.013(8) 0.7385(16) 1.1381(11) 0.084(19) Uiso 1 1 d D . . H1B H -0.1515(17) 0.779(2) 1.1194(13) 0.053(15) Uiso 1 1 d D . . C2 C 0.0797(7) 0.8338(3) 1.12521(16) 0.0434(14) Uani 1 1 d . . . H2A H 0.2115 0.8318 1.1138 0.052 Uiso 1 1 calc R . . C3 C -0.0260(8) 0.8837(2) 1.09883(15) 0.0450(14) Uani 1 1 d . . . H3A H -0.1567 0.8894 1.1104 0.054 Uiso 1 1 calc R . . O3 O 0.0833(5) 0.9426(2) 1.10402(10) 0.0561(10) Uani 1 1 d . . . C4 C -0.0334(7) 0.8647(3) 1.05138(15) 0.0469(14) Uani 1 1 d . . . H4A H -0.0560 0.8962 1.0302 0.056 Uiso 1 1 calc R . . C5 C -0.0094(8) 0.8057(3) 1.03867(14) 0.0395(13) Uani 1 1 d . . . Br5 Br 0.00405(9) 0.78248(3) 0.978240(15) 0.05391(17) Uani 1 1 d . . . C6 C 0.0146(8) 0.7498(2) 1.06895(14) 0.0486(14) Uani 1 1 d . . . H6A H -0.0786 0.7168 1.0616 0.058 Uiso 1 1 calc R . . H6B H 0.1425 0.7318 1.0655 0.058 Uiso 1 1 calc R . . C7 C 0.0932(8) 0.8449(3) 1.17398(18) 0.063(2) Uani 1 1 d . . . H7A H 0.1619 0.8099 1.1880 0.076 Uiso 1 1 calc R . . H7B H 0.1611 0.8846 1.1800 0.076 Uiso 1 1 calc R . . O7 O -0.1017(6) 0.8484(2) 1.19033(14) 0.0738(14) Uani 1 1 d . . . C8 C -0.1208(14) 0.8433(4) 1.2345(3) 0.100(3) Uani 1 1 d . . . O8 O 0.0195(11) 0.8382(3) 1.25716(15) 0.161(3) Uani 1 1 d . . . C9 C -0.3263(12) 0.8471(3) 1.2480(2) 0.123(3) Uani 1 1 d . . . H9A H -0.3358 0.8423 1.2794 0.184 Uiso 1 1 calc R . . H9B H -0.3977 0.8134 1.2338 0.184 Uiso 1 1 calc R . . H9C H -0.3783 0.8879 1.2395 0.184 Uiso 1 1 calc R . . C10 C -0.0117(11) 0.9980(3) 1.09321(19) 0.0625(16) Uani 1 1 d . . . O10 O -0.1754(7) 0.9977(2) 1.08189(15) 0.0868(15) Uani 1 1 d . . . C11 C 0.1122(9) 1.0551(3) 1.0994(2) 0.099(2) Uani 1 1 d . . . H11A H 0.0418 1.0930 1.0914 0.148 Uiso 1 1 calc R . . H11B H 0.2245 1.0514 1.0811 0.148 Uiso 1 1 calc R . . H11C H 0.1506 1.0580 1.1298 0.148 Uiso 1 1 calc R . . Cl21 Cl -0.46097(18) 0.76723(7) 1.12575(4) 0.0539(4) Uani 1 1 d . . . N21 N -0.3961(7) 0.6274(3) 1.15670(17) 0.0562(13) Uani 1 1 d D . . H21A H -0.417(6) 0.6713(8) 1.1465(13) 0.050(16) Uiso 1 1 d D . . H21B H -0.258(2) 0.632(4) 1.151(2) 0.17(3) Uiso 1 1 d D . . C22 C -0.4888(9) 0.6104(3) 1.19965(17) 0.0558(15) Uani 1 1 d . . . H22A H -0.6265 0.6035 1.1944 0.067 Uiso 1 1 calc R . . C23 C -0.4014(8) 0.5477(3) 1.2153(2) 0.0621(17) Uani 1 1 d . . . H23A H -0.2696 0.5550 1.2256 0.074 Uiso 1 1 calc R . . O23 O -0.5202(7) 0.5287(2) 1.25096(15) 0.0902(13) Uani 1 1 d . . . C24 C -0.4021(8) 0.4977(3) 1.1797(2) 0.0680(18) Uani 1 1 d . . . H24A H -0.3853 0.4548 1.1872 0.082 Uiso 1 1 calc R . . C25 C -0.4260(7) 0.5135(3) 1.1384(2) 0.0591(17) Uani 1 1 d . . . Br25 Br -0.42688(9) 0.45137(4) 1.09235(2) 0.0822(2) Uani 1 1 d . . . C26 C -0.4452(9) 0.5807(3) 1.12174(18) 0.0654(18) Uani 1 1 d . . . H26A H -0.3602 0.5868 1.0967 0.078 Uiso 1 1 calc R . . H26B H -0.5763 0.5880 1.1119 0.078 Uiso 1 1 calc R . . C27 C -0.4669(9) 0.6659(3) 1.23193(18) 0.0722(18) Uani 1 1 d . . . H27A H -0.5292 0.7039 1.2202 0.087 Uiso 1 1 calc R . . H27B H -0.5279 0.6551 1.2597 0.087 Uiso 1 1 calc R . . O27 O -0.2649(6) 0.6785(2) 1.23893(14) 0.0798(13) Uani 1 1 d . . . C28 C -0.1879(12) 0.6626(4) 1.2783(3) 0.087(2) Uani 1 1 d . . . O28 O -0.2805(8) 0.6424(3) 1.30728(18) 0.122(2) Uani 1 1 d . . . C29 C 0.0268(10) 0.6730(4) 1.2786(2) 0.130(3) Uani 1 1 d . . . H29A H 0.0773 0.6622 1.3072 0.195 Uiso 1 1 calc R . . H29B H 0.0542 0.7172 1.2723 0.195 Uiso 1 1 calc R . . H29C H 0.0856 0.6462 1.2567 0.195 Uiso 1 1 calc R . . C30 C -0.4376(17) 0.5022(5) 1.2871(3) 0.111(4) Uani 1 1 d . . . O30 O -0.2678(12) 0.4887(4) 1.2861(2) 0.151(3) Uani 1 1 d . . . C31 C -0.5691(13) 0.4935(4) 1.3243(2) 0.150(4) Uani 1 1 d . . . H31A H -0.5010 0.4741 1.3485 0.225 Uiso 1 1 calc R . . H31B H -0.6737 0.4662 1.3156 0.225 Uiso 1 1 calc R . . H31C H -0.6187 0.5344 1.3334 0.225 Uiso 1 1 calc R . . Cl41 Cl -0.45685(17) 0.32726(6) 1.01385(4) 0.0554(4) Uani 1 1 d . . . N41 N -0.8957(6) 0.3137(2) 1.01451(15) 0.0408(11) Uani 1 1 d D . . H41A H -0.7546(10) 0.315(2) 1.0143(15) 0.063(16) Uiso 1 1 d D . . H41B H -0.908(8) 0.2758(15) 0.9956(14) 0.10(2) Uiso 1 1 d D . . C42 C -0.9644(7) 0.3720(2) 0.99157(15) 0.0400(13) Uani 1 1 d . . . H42A H -1.1056 0.3725 0.9916 0.048 Uiso 1 1 calc R . . C43 C -0.8907(7) 0.4298(3) 1.01673(18) 0.0510(16) Uani 1 1 d . . . H43A H -0.7542 0.4365 1.0099 0.061 Uiso 1 1 calc R . . O43 O -1.0029(5) 0.48332(19) 0.99977(10) 0.0560(9) Uani 1 1 d . . . C44 C -0.9157(7) 0.4224(3) 1.06604(18) 0.0539(16) Uani 1 1 d . . . H44A H -0.9039 0.4583 1.0840 0.065 Uiso 1 1 calc R . . C45 C -0.9532(7) 0.3670(3) 1.08390(16) 0.0508(16) Uani 1 1 d . . . Br45 Br -0.98492(11) 0.35987(3) 1.145790(18) 0.0812(2) Uani 1 1 d . . . C46 C -0.9718(8) 0.3057(2) 1.05961(15) 0.0489(15) Uani 1 1 d . . . H46A H -0.9007 0.2723 1.0748 0.059 Uiso 1 1 calc R . . H46B H -1.1061 0.2931 1.0583 0.059 Uiso 1 1 calc R . . C47 C -0.8929(7) 0.3719(3) 0.94427(16) 0.0506(16) Uani 1 1 d . . . H47A H -0.9302 0.4112 0.9294 0.061 Uiso 1 1 calc R . . H47B H -0.7537 0.3683 0.9434 0.061 Uiso 1 1 calc R . . O47 O -0.9807(6) 0.31756(17) 0.92355(11) 0.0577(10) Uani 1 1 d . . . C48 C -0.9024(10) 0.2987(3) 0.8857(2) 0.071(2) Uani 1 1 d . . . O48 O -0.7757(8) 0.3272(3) 0.87006(17) 0.163(3) Uani 1 1 d . . . C49 C -1.0012(10) 0.2413(3) 0.86651(17) 0.087(2) Uani 1 1 d . . . H49A H -0.9385 0.2292 0.8395 0.130 Uiso 1 1 calc R . . H49B H -1.1335 0.2515 0.8606 0.130 Uiso 1 1 calc R . . H49C H -0.9949 0.2064 0.8871 0.130 Uiso 1 1 calc R . . C50 C -0.9202(11) 0.5428(3) 1.0048(2) 0.0666(19) Uani 1 1 d . . . O50 O -0.7749(6) 0.5514(2) 1.02405(14) 0.0781(13) Uani 1 1 d . . . C51 C -1.0437(11) 0.5922(3) 0.9835(2) 0.113(3) Uani 1 1 d . . . H51A H -0.9868 0.6338 0.9874 0.170 Uiso 1 1 calc R . . H51B H -1.1693 0.5916 0.9967 0.170 Uiso 1 1 calc R . . H51C H -1.0548 0.5830 0.9526 0.170 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 Cl1 0.0386(8) 0.0701(11) 0.0962(11) 0.0339(9) -0.0025(8) 0.0088(8) N1 0.044(3) 0.049(3) 0.038(3) 0.006(2) -0.001(3) 0.007(3) C2 0.043(3) 0.050(4) 0.037(3) -0.007(3) -0.006(3) 0.007(3) C3 0.049(3) 0.048(4) 0.038(3) -0.001(3) 0.004(3) 0.003(3) O3 0.061(2) 0.049(3) 0.059(3) -0.007(2) -0.0059(19) 0.005(2) C4 0.045(3) 0.058(4) 0.038(3) 0.014(3) 0.000(3) 0.015(4) C5 0.031(3) 0.042(4) 0.045(3) -0.002(3) -0.007(3) 0.005(3) Br5 0.0518(3) 0.0711(4) 0.0388(3) -0.0029(3) 0.0023(3) 0.0013(4) C6 0.055(3) 0.045(4) 0.046(3) -0.001(3) 0.005(3) 0.010(3) C7 0.070(4) 0.073(5) 0.048(5) -0.003(4) -0.006(3) 0.000(4) O7 0.093(3) 0.095(4) 0.034(3) -0.002(2) 0.008(2) 0.014(3) C8 0.138(8) 0.118(7) 0.044(6) 0.003(5) 0.011(5) 0.032(6) O8 0.180(6) 0.256(7) 0.048(3) 0.008(4) -0.016(4) 0.061(7) C9 0.184(9) 0.109(7) 0.075(6) 0.006(5) 0.054(6) 0.033(6) C10 0.076(5) 0.050(5) 0.061(4) -0.007(4) 0.002(5) 0.007(5) O10 0.086(3) 0.071(4) 0.103(4) -0.002(3) -0.016(3) 0.021(3) C11 0.123(6) 0.067(5) 0.106(6) -0.004(5) -0.022(5) -0.018(5) Cl21 0.0439(8) 0.0648(11) 0.0531(8) 0.0060(7) 0.0004(7) 0.0133(8) N21 0.059(3) 0.047(4) 0.062(4) 0.017(3) 0.005(3) 0.009(3) C22 0.048(3) 0.061(4) 0.058(4) 0.000(3) -0.013(4) 0.006(4) C23 0.053(4) 0.066(5) 0.068(5) 0.019(4) 0.004(3) -0.016(4) O23 0.102(3) 0.104(4) 0.065(3) 0.022(3) 0.008(3) -0.028(3) C24 0.068(4) 0.055(5) 0.081(5) 0.016(5) 0.001(4) -0.005(4) C25 0.040(3) 0.065(5) 0.073(5) -0.001(4) 0.003(3) 0.003(3) Br25 0.0638(4) 0.0896(6) 0.0930(5) -0.0195(5) -0.0114(4) 0.0108(4) C26 0.063(4) 0.075(5) 0.057(4) 0.001(4) 0.004(3) 0.008(4) C27 0.064(5) 0.085(5) 0.068(4) 0.005(4) -0.001(4) 0.014(4) O27 0.072(3) 0.104(4) 0.063(3) 0.000(3) -0.020(2) -0.004(3) C28 0.098(7) 0.092(7) 0.072(7) -0.009(5) -0.016(5) 0.011(5) O28 0.130(5) 0.161(6) 0.075(4) 0.013(4) -0.007(3) 0.004(4) C29 0.092(6) 0.169(8) 0.129(6) -0.016(6) -0.062(6) -0.016(6) C30 0.190(11) 0.070(6) 0.072(6) 0.008(5) 0.033(9) -0.034(8) O30 0.227(8) 0.146(6) 0.080(4) 0.054(4) 0.007(5) 0.042(6) C31 0.232(11) 0.155(8) 0.062(5) 0.024(5) 0.041(6) -0.041(8) Cl41 0.0351(8) 0.0497(9) 0.0815(10) -0.0040(8) -0.0009(8) 0.0001(7) N41 0.036(3) 0.044(3) 0.042(3) -0.003(3) 0.003(2) -0.001(2) C42 0.034(3) 0.033(3) 0.053(3) 0.000(3) -0.005(3) 0.000(3) C43 0.036(3) 0.058(4) 0.059(4) 0.002(4) 0.002(3) 0.005(3) O43 0.047(2) 0.052(3) 0.069(2) 0.008(2) 0.003(2) 0.010(3) C44 0.042(3) 0.072(5) 0.047(4) -0.022(4) 0.004(3) -0.003(3) C45 0.032(3) 0.082(5) 0.039(3) 0.012(4) 0.000(3) 0.002(4) Br45 0.0844(5) 0.1132(6) 0.0461(3) 0.0034(4) 0.0021(4) 0.0139(5) C46 0.047(4) 0.058(4) 0.042(3) 0.010(3) -0.011(3) -0.011(3) C47 0.051(3) 0.048(4) 0.054(4) -0.002(3) -0.002(3) -0.003(3) O47 0.067(2) 0.063(3) 0.043(2) -0.0035(19) 0.006(2) -0.010(3) C48 0.077(5) 0.078(6) 0.057(5) -0.007(4) 0.009(4) -0.017(4) O48 0.158(5) 0.219(7) 0.112(5) -0.083(4) 0.084(4) -0.114(5) C49 0.121(6) 0.069(5) 0.070(4) -0.013(3) -0.015(5) -0.020(5) C50 0.074(5) 0.050(5) 0.076(5) -0.007(4) 0.014(4) -0.005(5) O50 0.092(3) 0.060(3) 0.082(3) -0.001(3) -0.010(3) -0.021(3) C51 0.124(7) 0.057(5) 0.159(7) 0.012(5) -0.022(6) 0.025(5) _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 C6 1.488(5) . ? N1 C2 1.495(6) . ? C2 C7 1.500(6) . ? C2 C3 1.504(6) . ? C3 O3 1.451(6) . ? C3 C4 1.493(6) . ? O3 C10 1.369(7) . ? C4 C5 1.299(6) . ? C5 C6 1.493(6) . ? C5 Br5 1.898(4) . ? C7 O7 1.443(6) . ? O7 C8 1.351(8) . ? C8 O8 1.197(8) . ? C8 C9 1.487(10) . ? C10 O10 1.188(7) . ? C10 C11 1.481(8) . ? N21 C26 1.479(7) . ? N21 C22 1.496(6) . ? C22 C27 1.522(7) . ? C22 C23 1.517(7) . ? C23 O23 1.418(6) . ? C23 C24 1.500(8) . ? O23 C30 1.355(10) . ? C24 C25 1.307(7) . ? C25 C26 1.495(7) . ? C25 Br25 1.903(6) . ? C27 O27 1.443(7) . ? O27 C28 1.350(8) . ? C28 O28 1.166(8) . ? C28 C29 1.507(9) . ? C30 O30 1.213(10) . ? C30 C31 1.464(11) . ? N41 C46 1.475(6) . ? N41 C42 1.480(6) . ? C42 C43 1.514(6) . ? C42 C47 1.518(6) . ? C43 O43 1.455(5) . ? C43 C44 1.513(7) . ? O43 C50 1.375(7) . ? C44 C45 1.301(7) . ? C45 C46 1.480(7) . ? C45 Br45 1.896(5) . ? C47 O47 1.432(5) . ? O47 C48 1.331(6) . ? C48 O48 1.161(7) . ? C48 C49 1.497(7) . ? C50 O50 1.179(7) . ? C50 C51 1.487(8) . ? 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 C6 N1 C2 112.8(4) . . ? N1 C2 C7 111.0(4) . . ? N1 C2 C3 106.9(4) . . ? C7 C2 C3 116.6(5) . . ? O3 C3 C4 110.3(4) . . ? O3 C3 C2 105.8(4) . . ? C4 C3 C2 110.2(4) . . ? C10 O3 C3 115.7(4) . . ? C5 C4 C3 122.2(5) . . ? C4 C5 C6 124.8(4) . . ? C4 C5 Br5 122.3(4) . . ? C6 C5 Br5 112.9(3) . . ? N1 C6 C5 109.8(4) . . ? O7 C7 C2 106.7(4) . . ? C8 O7 C7 115.4(5) . . ? O8 C8 O7 119.8(8) . . ? O8 C8 C9 128.9(8) . . ? O7 C8 C9 111.3(7) . . ? O10 C10 O3 121.8(6) . . ? O10 C10 C11 126.6(7) . . ? O3 C10 C11 111.5(6) . . ? C26 N21 C22 111.7(5) . . ? N21 C22 C27 109.7(5) . . ? N21 C22 C23 107.6(5) . . ? C27 C22 C23 114.4(5) . . ? O23 C23 C24 110.7(5) . . ? O23 C23 C22 104.2(5) . . ? C24 C23 C22 111.9(5) . . ? C30 O23 C23 119.0(7) . . ? C25 C24 C23 121.0(6) . . ? C24 C25 C26 124.8(6) . . ? C24 C25 Br25 122.2(6) . . ? C26 C25 Br25 113.0(5) . . ? N21 C26 C25 110.8(5) . . ? O27 C27 C22 109.3(5) . . ? C28 O27 C27 118.0(5) . . ? O28 C28 O27 122.4(8) . . ? O28 C28 C29 126.3(8) . . ? O27 C28 C29 111.2(7) . . ? O30 C30 O23 119.1(10) . . ? O30 C30 C31 126.6(11) . . ? O23 C30 C31 114.3(10) . . ? C46 N41 C42 114.3(4) . . ? N41 C42 C43 107.9(4) . . ? N41 C42 C47 109.7(4) . . ? C43 C42 C47 111.5(4) . . ? O43 C43 C44 111.5(4) . . ? O43 C43 C42 104.5(4) . . ? C44 C43 C42 112.2(5) . . ? C50 O43 C43 115.4(5) . . ? C45 C44 C43 121.6(5) . . ? C44 C45 C46 125.2(5) . . ? C44 C45 Br45 120.3(5) . . ? C46 C45 Br45 114.5(4) . . ? N41 C46 C45 109.5(4) . . ? O47 C47 C42 106.1(4) . . ? C48 O47 C47 116.0(5) . . ? O48 C48 O47 120.7(7) . . ? O48 C48 C49 126.7(7) . . ? O47 C48 C49 112.5(6) . . ? O50 C50 O43 123.4(7) . . ? O50 C50 C51 127.1(7) . . ? O43 C50 C51 109.5(6) . . ? 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 N1 C2 C7 -165.2(5) . . . . ? C6 N1 C2 C3 66.6(5) . . . . ? N1 C2 C3 O3 -172.2(4) . . . . ? C7 C2 C3 O3 62.9(6) . . . . ? N1 C2 C3 C4 -53.0(5) . . . . ? C7 C2 C3 C4 -177.9(5) . . . . ? C4 C3 O3 C10 78.1(5) . . . . ? C2 C3 O3 C10 -162.7(4) . . . . ? O3 C3 C4 C5 137.0(5) . . . . ? C2 C3 C4 C5 20.5(8) . . . . ? C3 C4 C5 C6 4.3(9) . . . . ? C3 C4 C5 Br5 -174.3(4) . . . . ? C2 N1 C6 C5 -41.7(6) . . . . ? C4 C5 C6 N1 5.9(8) . . . . ? Br5 C5 C6 N1 -175.3(4) . . . . ? N1 C2 C7 O7 -63.6(6) . . . . ? C3 C2 C7 O7 59.2(7) . . . . ? C2 C7 O7 C8 165.2(5) . . . . ? C7 O7 C8 O8 2.1(12) . . . . ? C7 O7 C8 C9 -179.7(6) . . . . ? C3 O3 C10 O10 2.7(8) . . . . ? C3 O3 C10 C11 -179.7(4) . . . . ? C26 N21 C22 C27 -169.1(5) . . . . ? C26 N21 C22 C23 65.8(6) . . . . ? N21 C22 C23 O23 -169.2(4) . . . . ? C27 C22 C23 O23 68.6(6) . . . . ? N21 C22 C23 C24 -49.6(6) . . . . ? C27 C22 C23 C24 -171.8(5) . . . . ? C24 C23 O23 C30 99.0(7) . . . . ? C22 C23 O23 C30 -140.5(6) . . . . ? O23 C23 C24 C25 133.0(6) . . . . ? C22 C23 C24 C25 17.2(8) . . . . ? C23 C24 C25 C26 3.0(9) . . . . ? C23 C24 C25 Br25 179.8(4) . . . . ? C22 N21 C26 C25 -45.6(6) . . . . ? C24 C25 C26 N21 11.0(8) . . . . ? Br25 C25 C26 N21 -166.0(4) . . . . ? N21 C22 C27 O27 -59.9(6) . . . . ? C23 C22 C27 O27 61.1(6) . . . . ? C22 C27 O27 C28 -108.6(6) . . . . ? C27 O27 C28 O28 -4.1(11) . . . . ? C27 O27 C28 C29 174.5(6) . . . . ? C23 O23 C30 O30 -8.2(14) . . . . ? C23 O23 C30 C31 171.2(6) . . . . ? C46 N41 C42 C43 63.8(5) . . . . ? C46 N41 C42 C47 -174.6(4) . . . . ? N41 C42 C43 O43 -165.5(4) . . . . ? C47 C42 C43 O43 73.9(5) . . . . ? N41 C42 C43 C44 -44.6(5) . . . . ? C47 C42 C43 C44 -165.2(4) . . . . ? C44 C43 O43 C50 81.3(5) . . . . ? C42 C43 O43 C50 -157.3(4) . . . . ? O43 C43 C44 C45 131.8(5) . . . . ? C42 C43 C44 C45 15.0(7) . . . . ? C43 C44 C45 C46 1.4(8) . . . . ? C43 C44 C45 Br45 -179.7(3) . . . . ? C42 N41 C46 C45 -47.2(6) . . . . ? C44 C45 C46 N41 13.7(7) . . . . ? Br45 C45 C46 N41 -165.3(3) . . . . ? N41 C42 C47 O47 63.8(5) . . . . ? C43 C42 C47 O47 -176.8(4) . . . . ? C42 C47 O47 C48 -163.7(4) . . . . ? C47 O47 C48 O48 -3.1(9) . . . . ? C47 O47 C48 C49 179.4(5) . . . . ? C43 O43 C50 O50 -4.9(8) . . . . ? C43 O43 C50 C51 176.2(5) . . . . ? 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 N1 H1A Cl1 0.978(5) 2.22(3) 3.066(5) 144(4) . N1 H1B Cl21 0.980(5) 2.171(15) 3.123(5) 163(4) . N21 H21A Cl21 0.978(5) 2.117(8) 3.095(5) 179(4) . N21 H21B Cl1 0.980(5) 2.135(14) 3.105(5) 170(6) . N41 H41A Cl41 0.980(5) 2.084(8) 3.061(4) 174(4) . N41 H41B Cl41 0.980(5) 2.19(3) 3.090(5) 152(4) 4_457 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.253 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.045