# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jian Wang' _publ_contact_author_email chmwangj@nus.edu.sg loop_ _publ_author_name 'Yaojun Gao' 'Lei Wang' 'Swee-Meng Ang' 'Ren Qiao' 'Jian Wang' data_a583 _database_code_depnum_ccdc_archive 'CCDC 800850' #TrackingRef 'web_deposit_cif_file_0_JianWang_1289641398.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H17 Br O6' _chemical_formula_weight 457.27 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' 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 Triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 7.9684(10) _cell_length_b 10.9755(14) _cell_length_c 12.0108(15) _cell_angle_alpha 72.528(2) _cell_angle_beta 72.231(2) _cell_angle_gamma 83.350(2) _cell_volume 953.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1013 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 27.29 _exptl_crystal_description BLOCK _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.592 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 2.193 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3894 _exptl_absorpt_correction_T_max 0.6682 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 12359 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0731 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 27.49 _reflns_number_total 8512 _reflns_number_gt 7821 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0000P)^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 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 0.016(5) _refine_ls_number_reflns 8512 _refine_ls_number_parameters 527 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0330 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0698 _refine_ls_wR_factor_gt 0.0683 _refine_ls_goodness_of_fit_ref 0.857 _refine_ls_restrained_S_all 0.857 _refine_ls_shift/su_max 0.002 _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 0.14105(3) 0.32633(2) 0.43454(2) 0.02258(7) Uani 1 1 d . . . Br2 Br 0.16069(3) 0.59137(2) 1.15685(2) 0.02573(8) Uani 1 1 d . . . O1 O 0.8020(2) 0.24785(18) 0.07491(16) 0.0178(4) Uani 1 1 d . . . O2 O 0.8805(3) 0.3022(2) 0.21993(18) 0.0211(4) Uani 1 1 d . . . H2 H 0.9801 0.2825 0.1788 0.032 Uiso 1 1 calc R . . O3 O 0.2141(2) 0.2639(2) 0.05751(18) 0.0238(4) Uani 1 1 d . . . O4 O 0.9087(2) 0.2392(2) -0.15141(18) 0.0223(4) Uani 1 1 d . . . O5 O 0.8002(3) 0.01296(19) 0.22764(19) 0.0305(5) Uani 1 1 d . . . O6 O 0.6813(2) 0.08592(17) 0.39150(16) 0.0214(4) Uani 1 1 d . . . O7 O -0.0376(2) 0.56179(18) 0.73552(17) 0.0214(4) Uani 1 1 d . . . O8 O -0.2782(2) 0.50904(18) 0.90038(18) 0.0238(4) Uani 1 1 d . . . H8 H -0.3520 0.5410 0.8617 0.036 Uiso 1 1 calc R . . O9 O 0.5145(3) 0.63773(19) 0.76509(19) 0.0237(4) Uani 1 1 d . . . O10 O 0.1116(3) 0.5773(2) 0.50472(19) 0.0294(5) Uani 1 1 d . . . O11 O -0.1496(3) 0.80064(19) 0.72322(18) 0.0248(4) Uani 1 1 d . . . O12 O -0.2852(3) 0.75314(19) 0.92414(18) 0.0276(5) Uani 1 1 d . . . C1 C 0.7510(3) 0.2418(3) 0.2023(2) 0.0176(5) Uani 1 1 d . . . C2 C 0.5770(4) 0.3139(3) 0.2378(3) 0.0182(6) Uani 1 1 d . . . H2A H 0.5941 0.4062 0.1964 0.022 Uiso 1 1 calc R . . H2B H 0.5417 0.3025 0.3267 0.022 Uiso 1 1 calc R . . C3 C 0.4275(3) 0.2687(2) 0.2043(2) 0.0159(5) Uani 1 1 d . . . H3 H 0.3387 0.3409 0.1994 0.019 Uiso 1 1 calc R . . C4 C 0.4989(3) 0.2537(2) 0.0771(2) 0.0171(5) Uani 1 1 d . . . C5 C 0.6742(3) 0.2492(2) 0.0232(2) 0.0161(5) Uani 1 1 d . . . C6 C 0.7506(3) 0.2493(2) -0.1083(3) 0.0176(5) Uani 1 1 d . . . C7 C 0.6243(3) 0.2614(2) -0.1789(2) 0.0165(5) Uani 1 1 d . . . C8 C 0.4419(3) 0.2631(2) -0.1222(2) 0.0166(5) Uani 1 1 d . . . C9 C 0.3738(3) 0.2594(2) 0.0082(2) 0.0175(5) Uani 1 1 d . . . C10 C 0.6876(4) 0.2707(3) -0.3030(2) 0.0201(5) Uani 1 1 d . . . H10 H 0.8109 0.2704 -0.3413 0.024 Uiso 1 1 calc R . . C11 C 0.5706(4) 0.2802(3) -0.3704(3) 0.0245(6) Uani 1 1 d . . . H11 H 0.6135 0.2867 -0.4549 0.029 Uiso 1 1 calc R . . C12 C 0.3892(4) 0.2802(3) -0.3133(3) 0.0236(6) Uani 1 1 d . . . H12 H 0.3090 0.2858 -0.3592 0.028 Uiso 1 1 calc R . . C13 C 0.3255(4) 0.2721(3) -0.1906(2) 0.0193(5) Uani 1 1 d . . . H13 H 0.2020 0.2727 -0.1528 0.023 Uiso 1 1 calc R . . C14 C 0.3287(3) 0.1530(3) 0.2981(2) 0.0181(5) Uani 1 1 d . . . C15 C 0.1976(3) 0.1644(3) 0.4032(2) 0.0186(5) Uani 1 1 d . . . C16 C 0.1049(4) 0.0598(3) 0.4865(3) 0.0248(6) Uani 1 1 d . . . H16 H 0.0167 0.0703 0.5571 0.030 Uiso 1 1 calc R . . C17 C 0.1403(4) -0.0595(3) 0.4672(3) 0.0249(6) Uani 1 1 d . . . H17 H 0.0776 -0.1314 0.5246 0.030 Uiso 1 1 calc R . . C18 C 0.2687(4) -0.0732(3) 0.3629(3) 0.0260(6) Uani 1 1 d . . . H18 H 0.2931 -0.1547 0.3481 0.031 Uiso 1 1 calc R . . C19 C 0.3604(4) 0.0315(3) 0.2809(3) 0.0213(6) Uani 1 1 d . . . H19 H 0.4481 0.0204 0.2103 0.026 Uiso 1 1 calc R . . C20 C 0.7478(3) 0.0982(3) 0.2725(2) 0.0196(5) Uani 1 1 d . . . C21 C 0.6623(4) -0.0446(3) 0.4709(3) 0.0247(6) Uani 1 1 d . . . H21A H 0.7791 -0.0839 0.4756 0.030 Uiso 1 1 calc R . . H21B H 0.6048 -0.0972 0.4397 0.030 Uiso 1 1 calc R . . C22 C 0.5507(5) -0.0359(3) 0.5937(3) 0.0323(7) Uani 1 1 d . . . H22A H 0.6073 0.0189 0.6221 0.048 Uiso 1 1 calc R . . H22B H 0.5374 -0.1215 0.6513 0.048 Uiso 1 1 calc R . . H22C H 0.4344 0.0007 0.5881 0.048 Uiso 1 1 calc R . . C23 C -0.1305(3) 0.5836(3) 0.8529(2) 0.0193(6) Uani 1 1 d . . . C24 C -0.0184(3) 0.5415(3) 0.9394(2) 0.0195(5) Uani 1 1 d . . . H24A H 0.0007 0.4477 0.9578 0.023 Uiso 1 1 calc R . . H24B H -0.0832 0.5614 1.0168 0.023 Uiso 1 1 calc R . . C25 C 0.1603(3) 0.6046(2) 0.8902(2) 0.0180(5) Uani 1 1 d . . . H25 H 0.2405 0.5473 0.9345 0.022 Uiso 1 1 calc R . . C26 C 0.2341(4) 0.6080(2) 0.7583(2) 0.0176(5) Uani 1 1 d . . . C27 C 0.1344(3) 0.5865(2) 0.6930(2) 0.0177(5) Uani 1 1 d . . . C28 C 0.2086(3) 0.5862(3) 0.5621(2) 0.0191(5) Uani 1 1 d . . . C29 C 0.4016(4) 0.5985(3) 0.5088(3) 0.0199(5) Uani 1 1 d . . . C30 C 0.5067(4) 0.6166(3) 0.5765(3) 0.0193(5) Uani 1 1 d . . . C31 C 0.4245(4) 0.6226(3) 0.7035(3) 0.0187(5) Uani 1 1 d . . . C32 C 0.4798(4) 0.5908(3) 0.3907(3) 0.0267(7) Uani 1 1 d . . . H32 H 0.4095 0.5796 0.3434 0.032 Uiso 1 1 calc R . . C33 C 0.6616(4) 0.5997(3) 0.3421(3) 0.0315(8) Uani 1 1 d . . . H33 H 0.7151 0.5941 0.2614 0.038 Uiso 1 1 calc R . . C34 C 0.7654(4) 0.6163(3) 0.4090(3) 0.0278(6) Uani 1 1 d . . . H34 H 0.8894 0.6224 0.3744 0.033 Uiso 1 1 calc R . . C35 C 0.6886(4) 0.6241(3) 0.5277(3) 0.0237(6) Uani 1 1 d . . . H35 H 0.7598 0.6344 0.5747 0.028 Uiso 1 1 calc R . . C36 C 0.1525(3) 0.7338(3) 0.9150(2) 0.0174(5) Uani 1 1 d . . . C37 C 0.1403(4) 0.7421(3) 1.0306(2) 0.0202(6) Uani 1 1 d . . . C38 C 0.1132(4) 0.8571(3) 1.0603(3) 0.0248(6) Uani 1 1 d . . . H38 H 0.1013 0.8587 1.1410 0.030 Uiso 1 1 calc R . . C39 C 0.1036(4) 0.9699(3) 0.9701(3) 0.0270(6) Uani 1 1 d . . . H39 H 0.0828 1.0493 0.9890 0.032 Uiso 1 1 calc R . . C40 C 0.1244(4) 0.9658(3) 0.8528(3) 0.0258(6) Uani 1 1 d . . . H40 H 0.1226 1.0429 0.7902 0.031 Uiso 1 1 calc R . . C41 C 0.1477(3) 0.8499(3) 0.8262(3) 0.0204(6) Uani 1 1 d . . . H41 H 0.1609 0.8490 0.7452 0.025 Uiso 1 1 calc R . . C42 C -0.1870(3) 0.7272(3) 0.8230(3) 0.0205(6) Uani 1 1 d . . . C43 C -0.3627(4) 0.8817(3) 0.9095(3) 0.0319(7) Uani 1 1 d . . . H43A H -0.4632 0.8901 0.8753 0.038 Uiso 1 1 calc R . . H43B H -0.2741 0.9454 0.8537 0.038 Uiso 1 1 calc R . . C44 C -0.4235(5) 0.9028(3) 1.0321(3) 0.0387(8) Uani 1 1 d . . . H44A H -0.5036 0.8351 1.0881 0.058 Uiso 1 1 calc R . . H44B H -0.4855 0.9859 1.0271 0.058 Uiso 1 1 calc R . . H44C H -0.3216 0.9014 1.0620 0.058 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 0.02156(14) 0.02772(16) 0.01653(14) -0.00869(12) -0.00137(11) 0.00244(12) Br2 0.03297(17) 0.02509(16) 0.01609(15) -0.00405(12) -0.00630(12) 0.00465(13) O1 0.0118(9) 0.0254(10) 0.0148(9) -0.0061(8) -0.0018(7) 0.0000(7) O2 0.0194(10) 0.0274(11) 0.0172(10) -0.0070(8) -0.0035(8) -0.0056(9) O3 0.0131(9) 0.0314(11) 0.0244(11) -0.0061(9) -0.0036(8) 0.0000(8) O4 0.0136(10) 0.0317(11) 0.0202(10) -0.0082(9) -0.0024(8) 0.0009(8) O5 0.0345(12) 0.0257(11) 0.0269(11) -0.0102(9) -0.0015(9) 0.0047(9) O6 0.0256(10) 0.0189(10) 0.0159(9) -0.0017(8) -0.0036(8) -0.0011(8) O7 0.0175(9) 0.0274(10) 0.0204(10) -0.0089(8) -0.0049(8) -0.0003(8) O8 0.0179(9) 0.0211(10) 0.0276(11) -0.0001(8) -0.0051(8) -0.0042(8) O9 0.0226(11) 0.0268(11) 0.0251(11) -0.0082(9) -0.0100(9) -0.0024(8) O10 0.0229(11) 0.0448(14) 0.0276(11) -0.0206(10) -0.0090(9) 0.0039(9) O11 0.0236(10) 0.0239(10) 0.0201(10) 0.0012(8) -0.0028(8) -0.0029(8) O12 0.0341(12) 0.0207(10) 0.0209(10) -0.0044(8) -0.0012(9) 0.0049(9) C1 0.0136(12) 0.0248(14) 0.0135(12) -0.0063(11) -0.0012(10) -0.0015(10) C2 0.0165(14) 0.0175(13) 0.0183(14) -0.0055(11) -0.0006(11) -0.0018(11) C3 0.0138(12) 0.0174(13) 0.0138(12) -0.0045(10) -0.0006(10) 0.0009(10) C4 0.0175(13) 0.0140(12) 0.0169(13) -0.0020(10) -0.0037(10) 0.0013(10) C5 0.0170(13) 0.0135(12) 0.0154(13) -0.0008(10) -0.0039(10) -0.0024(10) C6 0.0178(13) 0.0143(13) 0.0198(14) -0.0041(11) -0.0049(11) 0.0004(10) C7 0.0157(12) 0.0145(12) 0.0182(13) -0.0036(10) -0.0039(10) -0.0012(10) C8 0.0167(13) 0.0138(12) 0.0189(13) -0.0033(10) -0.0054(10) -0.0008(10) C9 0.0150(12) 0.0119(12) 0.0221(14) -0.0016(10) -0.0034(10) -0.0007(9) C10 0.0190(13) 0.0238(14) 0.0166(13) -0.0051(11) -0.0039(11) -0.0020(11) C11 0.0329(16) 0.0234(15) 0.0172(14) -0.0050(11) -0.0076(12) -0.0020(12) C12 0.0297(15) 0.0202(14) 0.0250(15) -0.0042(11) -0.0157(13) -0.0015(12) C13 0.0164(13) 0.0178(13) 0.0234(14) -0.0034(11) -0.0066(11) -0.0026(10) C14 0.0141(12) 0.0239(14) 0.0144(12) -0.0018(10) -0.0044(10) -0.0012(10) C15 0.0168(13) 0.0229(14) 0.0150(13) -0.0042(11) -0.0048(10) 0.0011(10) C16 0.0192(14) 0.0332(16) 0.0160(14) -0.0015(12) -0.0008(11) -0.0034(12) C17 0.0225(14) 0.0268(15) 0.0183(13) 0.0052(11) -0.0050(11) -0.0058(11) C18 0.0262(15) 0.0198(14) 0.0287(16) -0.0029(12) -0.0066(12) -0.0012(11) C19 0.0208(14) 0.0243(14) 0.0168(13) -0.0056(11) -0.0025(11) -0.0006(11) C20 0.0155(12) 0.0223(14) 0.0184(13) -0.0023(11) -0.0041(10) -0.0010(10) C21 0.0259(15) 0.0197(14) 0.0229(14) 0.0009(11) -0.0062(12) 0.0003(11) C22 0.0402(18) 0.0260(16) 0.0226(15) 0.0027(12) -0.0063(14) -0.0016(14) C23 0.0172(13) 0.0215(14) 0.0184(13) -0.0053(11) -0.0039(11) -0.0007(11) C24 0.0209(13) 0.0162(13) 0.0181(13) -0.0014(10) -0.0042(11) -0.0006(10) C25 0.0183(13) 0.0149(12) 0.0175(13) -0.0010(10) -0.0034(11) -0.0014(10) C26 0.0207(13) 0.0135(12) 0.0184(13) -0.0049(10) -0.0053(11) 0.0004(10) C27 0.0155(12) 0.0167(12) 0.0193(13) -0.0044(11) -0.0042(10) 0.0022(10) C28 0.0179(13) 0.0192(13) 0.0210(14) -0.0085(11) -0.0051(11) 0.0028(10) C29 0.0197(13) 0.0198(13) 0.0206(14) -0.0089(11) -0.0045(11) 0.0023(10) C30 0.0225(14) 0.0156(13) 0.0197(14) -0.0066(11) -0.0049(11) 0.0006(11) C31 0.0183(13) 0.0148(13) 0.0204(14) -0.0038(11) -0.0034(11) 0.0008(10) C32 0.0284(17) 0.0319(17) 0.0224(16) -0.0117(13) -0.0072(13) 0.0006(13) C33 0.0289(18) 0.0406(19) 0.0227(16) -0.0138(14) 0.0005(14) -0.0004(15) C34 0.0174(14) 0.0349(17) 0.0295(17) -0.0127(14) -0.0002(13) -0.0016(12) C35 0.0186(14) 0.0275(16) 0.0252(15) -0.0088(12) -0.0048(12) -0.0017(12) C36 0.0144(12) 0.0181(13) 0.0185(13) -0.0067(10) -0.0018(10) 0.0006(10) C37 0.0213(13) 0.0193(13) 0.0148(13) -0.0009(11) -0.0015(11) -0.0010(11) C38 0.0274(15) 0.0288(16) 0.0181(14) -0.0100(12) -0.0024(12) -0.0017(12) C39 0.0291(16) 0.0227(14) 0.0307(16) -0.0150(13) -0.0040(13) 0.0012(12) C40 0.0290(15) 0.0175(14) 0.0261(16) -0.0015(12) -0.0051(13) -0.0022(12) C41 0.0191(13) 0.0212(14) 0.0173(13) -0.0046(11) 0.0007(11) -0.0044(11) C42 0.0150(13) 0.0212(14) 0.0230(14) -0.0053(11) -0.0024(11) -0.0017(10) C43 0.0378(18) 0.0260(16) 0.0290(17) -0.0087(13) -0.0069(14) 0.0068(13) C44 0.048(2) 0.0347(18) 0.0340(19) -0.0169(15) -0.0081(16) 0.0084(15) _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 C15 1.901(3) . ? Br2 C37 1.910(3) . ? O1 C5 1.341(3) . ? O1 C1 1.440(3) . ? O2 C1 1.388(3) . ? O3 C9 1.232(3) . ? O4 C6 1.213(3) . ? O5 C20 1.189(3) . ? O6 C20 1.334(3) . ? O6 C21 1.458(3) . ? O7 C27 1.337(3) . ? O7 C23 1.455(3) . ? O8 C23 1.383(3) . ? O9 C31 1.230(3) . ? O10 C28 1.210(3) . ? O11 C42 1.197(3) . ? O12 C42 1.321(3) . ? O12 C43 1.456(4) . ? C1 C2 1.522(4) . ? C1 C20 1.547(4) . ? C2 C3 1.542(4) . ? C3 C4 1.511(4) . ? C3 C14 1.527(4) . ? C4 C5 1.351(4) . ? C4 C9 1.462(4) . ? C5 C6 1.509(4) . ? C6 C7 1.473(4) . ? C7 C10 1.396(4) . ? C7 C8 1.405(4) . ? C8 C13 1.393(4) . ? C8 C9 1.482(4) . ? C10 C11 1.386(4) . ? C11 C12 1.398(4) . ? C12 C13 1.383(4) . ? C14 C19 1.393(4) . ? C14 C15 1.401(4) . ? C15 C16 1.385(4) . ? C16 C17 1.380(4) . ? C17 C18 1.391(4) . ? C18 C19 1.378(4) . ? C21 C22 1.496(4) . ? C23 C24 1.508(4) . ? C23 C42 1.553(4) . ? C24 C25 1.525(4) . ? C25 C26 1.503(4) . ? C25 C36 1.525(4) . ? C26 C27 1.355(4) . ? C26 C31 1.464(4) . ? C27 C28 1.503(4) . ? C28 C29 1.480(4) . ? C29 C32 1.389(4) . ? C29 C30 1.398(4) . ? C30 C35 1.389(4) . ? C30 C31 1.484(4) . ? C32 C33 1.390(5) . ? C33 C34 1.376(5) . ? C34 C35 1.394(4) . ? C36 C37 1.391(4) . ? C36 C41 1.400(4) . ? C37 C38 1.388(4) . ? C38 C39 1.391(4) . ? C39 C40 1.381(4) . ? C40 C41 1.380(4) . ? C43 C44 1.483(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 C5 O1 C1 118.06(19) . . ? C20 O6 C21 116.0(2) . . ? C27 O7 C23 116.6(2) . . ? C42 O12 C43 115.8(2) . . ? O2 C1 O1 106.8(2) . . ? O2 C1 C2 107.8(2) . . ? O1 C1 C2 111.2(2) . . ? O2 C1 C20 110.5(2) . . ? O1 C1 C20 106.2(2) . . ? C2 C1 C20 114.1(2) . . ? C1 C2 C3 112.9(2) . . ? C4 C3 C14 114.0(2) . . ? C4 C3 C2 108.6(2) . . ? C14 C3 C2 115.3(2) . . ? C5 C4 C9 120.4(2) . . ? C5 C4 C3 121.0(2) . . ? C9 C4 C3 118.2(2) . . ? O1 C5 C4 126.2(2) . . ? O1 C5 C6 111.1(2) . . ? C4 C5 C6 122.6(2) . . ? O4 C6 C7 122.9(3) . . ? O4 C6 C5 120.4(2) . . ? C7 C6 C5 116.7(2) . . ? C10 C7 C8 120.1(2) . . ? C10 C7 C6 119.4(2) . . ? C8 C7 C6 120.6(2) . . ? C13 C8 C7 119.4(2) . . ? C13 C8 C9 120.2(2) . . ? C7 C8 C9 120.4(2) . . ? O3 C9 C4 120.2(2) . . ? O3 C9 C8 120.6(2) . . ? C4 C9 C8 119.2(2) . . ? C11 C10 C7 120.1(2) . . ? C10 C11 C12 119.6(3) . . ? C13 C12 C11 120.6(3) . . ? C12 C13 C8 120.2(3) . . ? C19 C14 C15 116.7(2) . . ? C19 C14 C3 121.5(2) . . ? C15 C14 C3 121.8(2) . . ? C16 C15 C14 121.6(3) . . ? C16 C15 Br1 118.1(2) . . ? C14 C15 Br1 120.2(2) . . ? C17 C16 C15 120.3(3) . . ? C16 C17 C18 119.3(3) . . ? C19 C18 C17 119.9(3) . . ? C18 C19 C14 122.2(3) . . ? O5 C20 O6 125.6(3) . . ? O5 C20 C1 125.4(2) . . ? O6 C20 C1 109.0(2) . . ? O6 C21 C22 106.4(2) . . ? O8 C23 O7 106.7(2) . . ? O8 C23 C24 108.3(2) . . ? O7 C23 C24 111.0(2) . . ? O8 C23 C42 109.8(2) . . ? O7 C23 C42 105.0(2) . . ? C24 C23 C42 115.7(2) . . ? C23 C24 C25 113.6(2) . . ? C26 C25 C24 108.4(2) . . ? C26 C25 C36 114.4(2) . . ? C24 C25 C36 112.7(2) . . ? C27 C26 C31 119.5(2) . . ? C27 C26 C25 122.5(2) . . ? C31 C26 C25 117.7(2) . . ? O7 C27 C26 125.3(2) . . ? O7 C27 C28 112.0(2) . . ? C26 C27 C28 122.7(2) . . ? O10 C28 C29 122.9(2) . . ? O10 C28 C27 120.2(2) . . ? C29 C28 C27 116.9(2) . . ? C32 C29 C30 119.5(3) . . ? C32 C29 C28 119.7(3) . . ? C30 C29 C28 120.7(2) . . ? C35 C30 C29 120.6(3) . . ? C35 C30 C31 119.5(3) . . ? C29 C30 C31 119.8(2) . . ? O9 C31 C26 119.0(2) . . ? O9 C31 C30 120.9(2) . . ? C26 C31 C30 120.1(2) . . ? C29 C32 C33 119.5(3) . . ? C34 C33 C32 121.1(3) . . ? C33 C34 C35 120.0(3) . . ? C30 C35 C34 119.3(3) . . ? C37 C36 C41 116.1(2) . . ? C37 C36 C25 121.1(2) . . ? C41 C36 C25 122.7(2) . . ? C38 C37 C36 122.9(2) . . ? C38 C37 Br2 116.9(2) . . ? C36 C37 Br2 120.2(2) . . ? C37 C38 C39 118.9(3) . . ? C40 C39 C38 119.7(3) . . ? C41 C40 C39 120.2(3) . . ? C40 C41 C36 122.1(3) . . ? O11 C42 O12 126.3(3) . . ? O11 C42 C23 124.6(3) . . ? O12 C42 C23 109.1(2) . . ? O12 C43 C44 107.0(3) . . ? 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 O8 H8 O9 0.84 1.83 2.661(3) 168.8 1_455 O2 H2 O3 0.84 2.02 2.849(3) 169.9 1_655 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.654 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.069