# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2006 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_ohj82 _database_code_depnum_ccdc_archive 'CCDC 608269' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H19 B Br2 O2' _chemical_formula_weight 437.96 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' B B 0.0013 0.0007 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.074(2) _cell_length_b 11.835(2) _cell_length_c 15.537(3) _cell_angle_alpha 87.05(3) _cell_angle_beta 86.80(3) _cell_angle_gamma 63.69(3) _cell_volume 1821.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 14363 _cell_measurement_theta_min 4.823 _cell_measurement_theta_max 54.121 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.597 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 4.455 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5010 _exptl_absorpt_correction_T_max 0.8419 _exptl_absorpt_process_details sadabs _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 'Bruker Smart' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 47002 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 27.97 _reflns_number_total 8635 _reflns_number_gt 6590 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _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^)+(0.0228P)^2^+0.4198P] 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_number_reflns 8635 _refine_ls_number_parameters 423 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0301 _refine_ls_wR_factor_ref 0.0577 _refine_ls_wR_factor_gt 0.0532 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 B1 B 0.6027(3) 0.8677(2) 0.33290(16) 0.0188(6) Uani 1 1 d . . . Br1 Br 0.35406(2) 0.72000(2) 0.605190(14) 0.02516(6) Uani 1 1 d . . . Br2 Br 0.06251(2) 1.09586(2) 0.360957(15) 0.02763(7) Uani 1 1 d . . . O1 O 0.72921(14) 0.77102(12) 0.33564(9) 0.0195(3) Uani 1 1 d . . . O2 O 0.59221(14) 0.96317(13) 0.27547(9) 0.0223(3) Uani 1 1 d . . . C1 C 0.3607(2) 0.71581(19) 0.21012(13) 0.0196(5) Uani 1 1 d . . . C2 C 0.2451(2) 0.82508(19) 0.19466(14) 0.0213(5) Uani 1 1 d . . . H2 H 0.1723 0.8546 0.2361 0.026 Uiso 1 1 calc R . . C3 C 0.2378(2) 0.89051(19) 0.11736(14) 0.0211(5) Uani 1 1 d . . . C4 C 0.3431(2) 0.84874(19) 0.05660(14) 0.0201(5) Uani 1 1 d . . . H4 H 0.3351 0.8948 0.0036 0.024 Uiso 1 1 calc R . . C5 C 0.4611(2) 0.73938(18) 0.07253(13) 0.0169(5) Uani 1 1 d . . . C6 C 0.4711(2) 0.67024(18) 0.15100(13) 0.0178(5) Uani 1 1 d . . . C7 C 0.5941(2) 0.55132(19) 0.16885(13) 0.0188(5) Uani 1 1 d . . . C8 C 0.6300(2) 0.44749(19) 0.11771(14) 0.0214(5) Uani 1 1 d . . . H8 H 0.5752 0.4526 0.0713 0.026 Uiso 1 1 calc R . . C9 C 0.7442(2) 0.3371(2) 0.13348(15) 0.0258(5) Uani 1 1 d . . . H9 H 0.7669 0.2665 0.0984 0.031 Uiso 1 1 calc R . . C10 C 0.8255(2) 0.3289(2) 0.20002(15) 0.0267(6) Uani 1 1 d . . . H10 H 0.9047 0.2531 0.2104 0.032 Uiso 1 1 calc R . . C11 C 0.7914(2) 0.4315(2) 0.25167(15) 0.0264(5) Uani 1 1 d . . . H11 H 0.8471 0.4261 0.2975 0.032 Uiso 1 1 calc R . . C12 C 0.6761(2) 0.5417(2) 0.23650(14) 0.0233(5) Uani 1 1 d . . . H12 H 0.6526 0.6115 0.2725 0.028 Uiso 1 1 calc R . . C13 C 0.7595(2) 0.6079(2) -0.08865(13) 0.0217(5) Uani 1 1 d . . . C14 C 0.6528(2) 0.7226(2) -0.13840(14) 0.0204(5) Uani 1 1 d . . . C15 C 0.7612(2) 0.4827(2) -0.10983(15) 0.0300(6) Uani 1 1 d . . . H15A H 0.8167 0.4169 -0.0687 0.045 Uiso 1 1 calc R . . H15B H 0.7989 0.4597 -0.1685 0.045 Uiso 1 1 calc R . . H15C H 0.6690 0.4911 -0.1059 0.045 Uiso 1 1 calc R . . C16 C 0.9002(2) 0.6002(2) -0.09612(15) 0.0315(6) Uani 1 1 d . . . H16D H 0.9001 0.6731 -0.0688 0.047 Uiso 1 1 calc R . . H16E H 0.9279 0.6002 -0.1571 0.047 Uiso 1 1 calc R . . H16F H 0.9634 0.5224 -0.0672 0.047 Uiso 1 1 calc R . . C17 C 0.6790(2) 0.8385(2) -0.13980(15) 0.0282(6) Uani 1 1 d . . . H17A H 0.5994 0.9123 -0.1601 0.042 Uiso 1 1 calc R . . H17B H 0.7566 0.8254 -0.1787 0.042 Uiso 1 1 calc R . . H17C H 0.6980 0.8526 -0.0815 0.042 Uiso 1 1 calc R . . C18 C 0.6262(2) 0.6967(2) -0.22780(14) 0.0324(6) Uani 1 1 d . . . H18D H 0.5926 0.6325 -0.2241 0.049 Uiso 1 1 calc R . . H18E H 0.7100 0.6661 -0.2632 0.049 Uiso 1 1 calc R . . H18F H 0.5586 0.7745 -0.2541 0.049 Uiso 1 1 calc R . . B1' B 0.5717(2) 0.7040(2) -0.00297(16) 0.0179(5) Uani 1 1 d . . . Br1' Br 0.35843(2) 0.62378(2) 0.314212(14) 0.02650(7) Uani 1 1 d . . . Br2' Br 0.07883(2) 1.03929(2) 0.093138(15) 0.02871(7) Uani 1 1 d . . . O1' O 0.70686(14) 0.63174(13) 0.00143(9) 0.0209(3) Uani 1 1 d . . . O2' O 0.53044(14) 0.75159(13) -0.08369(9) 0.0200(3) Uani 1 1 d . . . C1' C 0.3571(2) 0.81553(19) 0.50286(13) 0.0183(5) Uani 1 1 d . . . C2' C 0.2337(2) 0.90214(19) 0.47362(13) 0.0200(5) Uani 1 1 d . . . H2' H 0.1522 0.9111 0.5024 0.024 Uiso 1 1 calc R . . C3' C 0.2322(2) 0.97537(19) 0.40131(14) 0.0201(5) Uani 1 1 d . . . C4' C 0.3503(2) 0.96359(19) 0.35835(14) 0.0196(5) Uani 1 1 d . . . H4' H 0.3460 1.0159 0.3090 0.024 Uiso 1 1 calc R . . C5' C 0.4754(2) 0.87515(19) 0.38724(13) 0.0177(5) Uani 1 1 d . . . C6' C 0.4797(2) 0.79888(19) 0.46140(13) 0.0171(5) Uani 1 1 d . . . C7' C 0.6107(2) 0.70278(19) 0.49456(13) 0.0188(5) Uani 1 1 d . . . C8' C 0.6513(2) 0.5748(2) 0.48241(14) 0.0232(5) Uani 1 1 d . . . H8' H 0.5947 0.5486 0.4540 0.028 Uiso 1 1 calc R . . C9' C 0.7741(2) 0.4863(2) 0.51180(15) 0.0299(6) Uani 1 1 d . . . H9' H 0.8017 0.3992 0.5036 0.036 Uiso 1 1 calc R . . C10' C 0.8565(2) 0.5240(2) 0.55301(15) 0.0321(6) Uani 1 1 d . . . H10' H 0.9407 0.4627 0.5731 0.038 Uiso 1 1 calc R . . C11' C 0.8175(2) 0.6504(2) 0.56532(15) 0.0321(6) Uani 1 1 d . . . H11' H 0.8745 0.6758 0.5940 0.039 Uiso 1 1 calc R . . C12' C 0.6953(2) 0.7399(2) 0.53576(14) 0.0248(5) Uani 1 1 d . . . H12' H 0.6690 0.8268 0.5436 0.030 Uiso 1 1 calc R . . C13' C 0.8187(2) 0.81526(19) 0.28563(14) 0.0201(5) Uani 1 1 d . . . C14' C 0.7200(2) 0.91910(19) 0.22472(14) 0.0207(5) Uani 1 1 d . . . C15' C 0.9294(2) 0.7040(2) 0.24034(15) 0.0296(6) Uani 1 1 d . . . H15D H 0.9884 0.6445 0.2833 0.044 Uiso 1 1 calc R . . H15E H 0.9822 0.7339 0.2011 0.044 Uiso 1 1 calc R . . H15F H 0.8891 0.6618 0.2074 0.044 Uiso 1 1 calc R . . C16' C 0.8780(2) 0.8661(2) 0.35123(16) 0.0329(6) Uani 1 1 d . . . H16A H 0.8054 0.9383 0.3796 0.049 Uiso 1 1 calc R . . H16B H 0.9420 0.8930 0.3218 0.049 Uiso 1 1 calc R . . H16C H 0.9249 0.7999 0.3945 0.049 Uiso 1 1 calc R . . C17' C 0.7515(2) 1.0301(2) 0.20359(16) 0.0306(6) Uani 1 1 d . . . H17D H 0.6824 1.0915 0.1664 0.046 Uiso 1 1 calc R . . H17E H 0.8400 1.0003 0.1737 0.046 Uiso 1 1 calc R . . H17F H 0.7525 1.0701 0.2571 0.046 Uiso 1 1 calc R . . C18' C 0.6987(2) 0.8673(2) 0.14234(14) 0.0306(6) Uani 1 1 d . . . H18A H 0.6783 0.7958 0.1567 0.046 Uiso 1 1 calc R . . H18B H 0.7807 0.8392 0.1053 0.046 Uiso 1 1 calc R . . H18C H 0.6233 0.9335 0.1119 0.046 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 B1 0.0236(14) 0.0192(13) 0.0145(13) -0.0016(10) -0.0010(11) -0.0104(11) Br1 0.02825(13) 0.02785(13) 0.01788(12) 0.00398(10) 0.00598(10) -0.01228(10) Br2 0.01900(13) 0.02869(13) 0.02901(14) 0.00402(10) 0.00104(10) -0.00565(10) O1 0.0192(8) 0.0180(8) 0.0177(8) 0.0013(6) 0.0054(6) -0.0059(6) O2 0.0177(8) 0.0218(8) 0.0225(9) 0.0042(7) 0.0077(7) -0.0059(7) C1 0.0286(13) 0.0201(11) 0.0142(12) -0.0029(9) 0.0049(10) -0.0147(10) C2 0.0209(12) 0.0240(12) 0.0218(13) -0.0091(10) 0.0081(10) -0.0125(10) C3 0.0176(12) 0.0180(11) 0.0264(13) -0.0042(10) 0.0030(10) -0.0069(9) C4 0.0219(12) 0.0208(12) 0.0178(12) -0.0010(9) 0.0014(10) -0.0098(10) C5 0.0195(12) 0.0157(11) 0.0173(12) -0.0015(9) 0.0018(9) -0.0096(9) C6 0.0226(12) 0.0177(11) 0.0157(12) -0.0044(9) 0.0037(9) -0.0115(10) C7 0.0221(12) 0.0188(11) 0.0169(12) -0.0001(9) 0.0068(10) -0.0114(10) C8 0.0256(13) 0.0217(12) 0.0190(12) -0.0011(10) 0.0031(10) -0.0129(10) C9 0.0299(14) 0.0205(12) 0.0258(14) -0.0037(10) 0.0064(11) -0.0106(11) C10 0.0259(13) 0.0204(12) 0.0265(14) 0.0078(10) 0.0063(11) -0.0054(10) C11 0.0287(14) 0.0323(14) 0.0188(13) 0.0060(11) -0.0024(10) -0.0146(11) C12 0.0318(14) 0.0229(12) 0.0179(12) -0.0007(10) 0.0059(10) -0.0153(11) C13 0.0182(12) 0.0271(12) 0.0151(12) -0.0012(10) 0.0069(9) -0.0066(10) C14 0.0145(11) 0.0274(12) 0.0161(12) -0.0004(10) 0.0068(9) -0.0073(10) C15 0.0292(14) 0.0245(13) 0.0295(14) -0.0053(11) 0.0112(11) -0.0065(11) C16 0.0210(13) 0.0426(15) 0.0246(14) 0.0044(11) 0.0028(11) -0.0094(11) C17 0.0260(13) 0.0309(13) 0.0259(14) 0.0086(11) 0.0018(11) -0.0122(11) C18 0.0285(14) 0.0440(15) 0.0177(13) -0.0039(11) 0.0030(11) -0.0098(12) B1' 0.0232(14) 0.0125(12) 0.0191(14) -0.0040(10) 0.0042(11) -0.0091(11) Br1' 0.03484(14) 0.02991(13) 0.01687(12) -0.00180(10) 0.00858(10) -0.01719(11) Br2' 0.01768(13) 0.02938(13) 0.03262(15) -0.00441(11) 0.00282(10) -0.00462(10) O1' 0.0205(8) 0.0226(8) 0.0142(8) 0.0009(6) 0.0040(6) -0.0052(7) O2' 0.0166(8) 0.0248(8) 0.0159(8) -0.0011(7) 0.0053(6) -0.0073(7) C1' 0.0261(13) 0.0176(11) 0.0133(11) -0.0013(9) 0.0040(10) -0.0119(10) C2' 0.0194(12) 0.0223(12) 0.0194(12) -0.0051(10) 0.0059(10) -0.0106(10) C3' 0.0194(12) 0.0178(11) 0.0192(12) -0.0021(9) 0.0026(10) -0.0047(9) C4' 0.0244(13) 0.0185(11) 0.0163(12) 0.0008(9) 0.0031(10) -0.0103(10) C5' 0.0207(12) 0.0174(11) 0.0158(12) -0.0020(9) 0.0039(9) -0.0096(10) C6' 0.0209(12) 0.0180(11) 0.0143(11) -0.0050(9) 0.0033(9) -0.0101(9) C7' 0.0208(12) 0.0230(12) 0.0106(11) 0.0016(9) 0.0059(9) -0.0089(10) C8' 0.0250(13) 0.0232(12) 0.0213(13) 0.0000(10) 0.0031(10) -0.0110(10) C9' 0.0281(14) 0.0231(13) 0.0286(14) 0.0061(11) 0.0065(11) -0.0040(11) C10' 0.0194(13) 0.0445(16) 0.0224(14) 0.0121(12) 0.0030(11) -0.0069(12) C11' 0.0266(14) 0.0516(17) 0.0200(13) 0.0021(12) -0.0007(11) -0.0193(13) C12' 0.0278(14) 0.0294(13) 0.0181(12) -0.0037(10) 0.0053(10) -0.0139(11) C13' 0.0182(12) 0.0222(12) 0.0198(12) -0.0020(10) 0.0072(10) -0.0094(10) C14' 0.0166(12) 0.0224(12) 0.0201(12) 0.0002(10) 0.0075(10) -0.0069(10) C15' 0.0237(13) 0.0258(13) 0.0294(14) -0.0006(11) 0.0094(11) -0.0031(10) C16' 0.0262(14) 0.0428(15) 0.0317(15) -0.0059(12) 0.0017(11) -0.0168(12) C17' 0.0280(14) 0.0250(13) 0.0371(15) 0.0017(11) 0.0129(12) -0.0120(11) C18' 0.0319(14) 0.0395(15) 0.0215(13) 0.0017(11) 0.0016(11) -0.0173(12) _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 B1 O1 1.362(3) . ? B1 O2 1.370(3) . ? B1 C5' 1.572(3) . ? Br1 C1' 1.910(2) . ? Br2 C3' 1.903(2) . ? O1 C13' 1.480(2) . ? O2 C14' 1.469(2) . ? C1 C2 1.380(3) . ? C1 C6 1.404(3) . ? C1 Br1' 1.908(2) . ? C2 C3 1.381(3) . ? C2 H2 0.9500 . ? C3 C4 1.382(3) . ? C3 Br2' 1.897(2) . ? C4 C5 1.396(3) . ? C4 H4 0.9500 . ? C5 C6 1.414(3) . ? C5 B1' 1.577(3) . ? C6 C7 1.489(3) . ? C7 C8 1.390(3) . ? C7 C12 1.395(3) . ? C8 C9 1.380(3) . ? C8 H8 0.9500 . ? C9 C10 1.381(3) . ? C9 H9 0.9500 . ? C10 C11 1.386(3) . ? C10 H10 0.9500 . ? C11 C12 1.383(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 O1' 1.477(2) . ? C13 C16 1.518(3) . ? C13 C15 1.526(3) . ? C13 C14 1.552(3) . ? C14 O2' 1.472(2) . ? C14 C18 1.510(3) . ? C14 C17 1.522(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16D 0.9800 . ? C16 H16E 0.9800 . ? C16 H16F 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18D 0.9800 . ? C18 H18E 0.9800 . ? C18 H18F 0.9800 . ? B1' O1' 1.359(3) . ? B1' O2' 1.364(3) . ? C1' C2' 1.380(3) . ? C1' C6' 1.405(3) . ? C2' C3' 1.379(3) . ? C2' H2' 0.9500 . ? C3' C4' 1.387(3) . ? C4' C5' 1.398(3) . ? C4' H4' 0.9500 . ? C5' C6' 1.416(3) . ? C6' C7' 1.491(3) . ? C7' C12' 1.393(3) . ? C7' C8' 1.395(3) . ? C8' C9' 1.383(3) . ? C8' H8' 0.9500 . ? C9' C10' 1.378(3) . ? C9' H9' 0.9500 . ? C10' C11' 1.381(3) . ? C10' H10' 0.9500 . ? C11' C12' 1.383(3) . ? C11' H11' 0.9500 . ? C12' H12' 0.9500 . ? C13' C15' 1.516(3) . ? C13' C16' 1.524(3) . ? C13' C14' 1.551(3) . ? C14' C17' 1.518(3) . ? C14' C18' 1.521(3) . ? C15' H15D 0.9800 . ? C15' H15E 0.9800 . ? C15' H15F 0.9800 . ? C16' H16A 0.9800 . ? C16' H16B 0.9800 . ? C16' H16C 0.9800 . ? C17' H17D 0.9800 . ? C17' H17E 0.9800 . ? C17' H17F 0.9800 . ? C18' H18A 0.9800 . ? C18' H18B 0.9800 . ? C18' H18C 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 O1 B1 O2 113.6(2) . . ? O1 B1 C5' 126.0(2) . . ? O2 B1 C5' 120.4(2) . . ? B1 O1 C13' 106.34(16) . . ? B1 O2 C14' 107.29(16) . . ? C2 C1 C6 122.5(2) . . ? C2 C1 Br1' 116.02(16) . . ? C6 C1 Br1' 121.39(16) . . ? C1 C2 C3 118.35(19) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C2 C3 C4 121.4(2) . . ? C2 C3 Br2' 119.40(16) . . ? C4 C3 Br2' 119.22(17) . . ? C3 C4 C5 120.5(2) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C5 C6 119.33(19) . . ? C4 C5 B1' 114.45(19) . . ? C6 C5 B1' 126.21(19) . . ? C1 C6 C5 117.95(19) . . ? C1 C6 C7 121.42(19) . . ? C5 C6 C7 120.61(18) . . ? C8 C7 C12 118.6(2) . . ? C8 C7 C6 120.4(2) . . ? C12 C7 C6 121.01(18) . . ? C9 C8 C7 120.8(2) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 120.2(2) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C9 C10 C11 119.8(2) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 120.0(2) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C7 120.6(2) . . ? C11 C12 H12 119.7 . . ? C7 C12 H12 119.7 . . ? O1' C13 C16 109.84(18) . . ? O1' C13 C15 105.52(17) . . ? C16 C13 C15 111.29(18) . . ? O1' C13 C14 102.31(15) . . ? C16 C13 C14 113.86(18) . . ? C15 C13 C14 113.25(19) . . ? O2' C14 C18 108.17(17) . . ? O2' C14 C17 106.75(17) . . ? C18 C14 C17 110.77(19) . . ? O2' C14 C13 101.70(16) . . ? C18 C14 C13 115.49(18) . . ? C17 C14 C13 113.07(18) . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16D 109.5 . . ? C13 C16 H16E 109.5 . . ? H16D C16 H16E 109.5 . . ? C13 C16 H16F 109.5 . . ? H16D C16 H16F 109.5 . . ? H16E C16 H16F 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18D 109.5 . . ? C14 C18 H18E 109.5 . . ? H18D C18 H18E 109.5 . . ? C14 C18 H18F 109.5 . . ? H18D C18 H18F 109.5 . . ? H18E C18 H18F 109.5 . . ? O1' B1' O2' 113.97(19) . . ? O1' B1' C5 128.2(2) . . ? O2' B1' C5 117.82(19) . . ? B1' O1' C13 106.08(17) . . ? B1' O2' C14 106.97(16) . . ? C2' C1' C6' 122.5(2) . . ? C2' C1' Br1 116.49(16) . . ? C6' C1' Br1 120.96(16) . . ? C3' C2' C1' 118.1(2) . . ? C3' C2' H2' 121.0 . . ? C1' C2' H2' 121.0 . . ? C2' C3' C4' 121.8(2) . . ? C2' C3' Br2 118.35(16) . . ? C4' C3' Br2 119.87(17) . . ? C3' C4' C5' 120.4(2) . . ? C3' C4' H4' 119.8 . . ? C5' C4' H4' 119.8 . . ? C4' C5' C6' 118.97(19) . . ? C4' C5' B1 116.25(19) . . ? C6' C5' B1 124.77(19) . . ? C1' C6' C5' 118.29(19) . . ? C1' C6' C7' 120.70(19) . . ? C5' C6' C7' 121.01(18) . . ? C12' C7' C8' 119.4(2) . . ? C12' C7' C6' 120.44(19) . . ? C8' C7' C6' 120.2(2) . . ? C9' C8' C7' 119.9(2) . . ? C9' C8' H8' 120.0 . . ? C7' C8' H8' 120.0 . . ? C10' C9' C8' 120.2(2) . . ? C10' C9' H9' 119.9 . . ? C8' C9' H9' 119.9 . . ? C9' C10' C11' 120.4(2) . . ? C9' C10' H10' 119.8 . . ? C11' C10' H10' 119.8 . . ? C10' C11' C12' 119.9(2) . . ? C10' C11' H11' 120.0 . . ? C12' C11' H11' 120.0 . . ? C11' C12' C7' 120.2(2) . . ? C11' C12' H12' 119.9 . . ? C7' C12' H12' 119.9 . . ? O1 C13' C15' 108.71(16) . . ? O1 C13' C16' 106.02(17) . . ? C15' C13' C16' 110.45(19) . . ? O1 C13' C14' 102.64(16) . . ? C15' C13' C14' 114.86(18) . . ? C16' C13' C14' 113.40(18) . . ? O2 C14' C17' 108.97(16) . . ? O2 C14' C18' 106.49(17) . . ? C17' C14' C18' 110.18(19) . . ? O2 C14' C13' 101.88(16) . . ? C17' C14' C13' 115.50(19) . . ? C18' C14' C13' 113.05(18) . . ? C13' C15' H15D 109.5 . . ? C13' C15' H15E 109.5 . . ? H15D C15' H15E 109.5 . . ? C13' C15' H15F 109.5 . . ? H15D C15' H15F 109.5 . . ? H15E C15' H15F 109.5 . . ? C13' C16' H16A 109.5 . . ? C13' C16' H16B 109.5 . . ? H16A C16' H16B 109.5 . . ? C13' C16' H16C 109.5 . . ? H16A C16' H16C 109.5 . . ? H16B C16' H16C 109.5 . . ? C14' C17' H17D 109.5 . . ? C14' C17' H17E 109.5 . . ? H17D C17' H17E 109.5 . . ? C14' C17' H17F 109.5 . . ? H17D C17' H17F 109.5 . . ? H17E C17' H17F 109.5 . . ? C14' C18' H18A 109.5 . . ? C14' C18' H18B 109.5 . . ? H18A C18' H18B 109.5 . . ? C14' C18' H18C 109.5 . . ? H18A C18' H18C 109.5 . . ? H18B C18' H18C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.97 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.526 _refine_diff_density_min -0.490 _refine_diff_density_rms 0.082 data_ohj87 _database_code_depnum_ccdc_archive 'CCDC 608270' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 B Br O4' _chemical_formula_weight 417.10 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.0909(5) _cell_length_b 21.9946(12) _cell_length_c 11.5867(7) _cell_angle_alpha 90.00 _cell_angle_beta 106.399(3) _cell_angle_gamma 90.00 _cell_volume 1978.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7760 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 26.90 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 2.099 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.5910 _exptl_absorpt_correction_T_max 0.9207 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 36671 _diffrn_reflns_av_R_equivalents 0.0475 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4548 _reflns_number_gt 3641 _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^+11.7368P] 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_number_reflns 4548 _refine_ls_number_parameters 309 _refine_ls_number_restraints 178 _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_gt 0.0627 _refine_ls_wR_factor_ref 0.1546 _refine_ls_wR_factor_gt 0.1490 _refine_ls_goodness_of_fit_ref 1.209 _refine_ls_restrained_S_all 1.191 _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 Br1 Br 0.11051(8) 0.71101(2) 0.29096(6) 0.04328(18) Uani 1 1 d . . . B1 B 0.3198(7) 0.9350(2) 0.1750(5) 0.0235(10) Uani 1 1 d . . . O1 O 0.2029(13) 0.9704(4) 0.2115(8) 0.0278(17) Uani 0.489(5) 1 d PU A 1 O2 O 0.4729(9) 0.9676(3) 0.2097(7) 0.0245(13) Uani 0.489(5) 1 d PU A 1 C13 C 0.4225(13) 1.0307(4) 0.2267(9) 0.0275(10) Uani 0.489(5) 1 d PU A 1 C14 C 0.2318(14) 1.0313(4) 0.1512(11) 0.0288(11) Uani 0.489(5) 1 d PU A 1 C15 C 0.2098(16) 1.0506(6) 0.0204(11) 0.0331(17) Uani 0.489(5) 1 d PU A 1 H15A H 0.2404 1.0936 0.0180 0.050 Uiso 0.489(5) 1 calc PR A 1 H15B H 0.0897 1.0446 -0.0267 0.050 Uiso 0.489(5) 1 calc PR A 1 H15C H 0.2852 1.0258 -0.0137 0.050 Uiso 0.489(5) 1 calc PR A 1 C17 C 0.4497(16) 1.0385(6) 0.3598(12) 0.0299(18) Uani 0.489(5) 1 d PU A 1 H17A H 0.5733 1.0374 0.4013 0.045 Uiso 0.489(5) 1 calc PR A 1 H17B H 0.3914 1.0056 0.3898 0.045 Uiso 0.489(5) 1 calc PR A 1 H17C H 0.4020 1.0777 0.3749 0.045 Uiso 0.489(5) 1 calc PR A 1 C16 C 0.538(3) 1.0741(9) 0.1877(14) 0.0288(19) Uani 0.489(5) 1 d PU A 1 H16A H 0.6557 1.0702 0.2409 0.043 Uiso 0.489(5) 1 calc PR A 1 H16B H 0.4971 1.1158 0.1918 0.043 Uiso 0.489(5) 1 calc PR A 1 H16C H 0.5376 1.0649 0.1049 0.043 Uiso 0.489(5) 1 calc PR A 1 C18 C 0.1386(19) 1.0769(7) 0.2157(13) 0.0335(18) Uani 0.489(5) 1 d PU A 1 H18A H 0.1524 1.0632 0.2984 0.050 Uiso 0.489(5) 1 calc PR A 1 H18B H 0.0158 1.0785 0.1721 0.050 Uiso 0.489(5) 1 calc PR A 1 H18C H 0.1893 1.1174 0.2168 0.050 Uiso 0.489(5) 1 calc PR A 1 O1' O 0.1794(13) 0.9678(4) 0.1512(8) 0.0291(17) Uani 0.511(5) 1 d PU A 2 O2' O 0.4296(9) 0.9681(3) 0.1294(7) 0.0234(12) Uani 0.511(5) 1 d PU A 2 C13' C 0.3803(13) 1.0327(4) 0.1307(9) 0.0279(10) Uani 0.511(5) 1 d PU A 2 C14' C 0.2735(14) 1.0324(4) 0.2227(10) 0.0287(10) Uani 0.511(5) 1 d PU A 2 C16' C 0.547(3) 1.0697(9) 0.1624(13) 0.0302(19) Uani 0.511(5) 1 d PU A 2 H16D H 0.6019 1.0661 0.0974 0.045 Uiso 0.511(5) 1 calc PR A 2 H16E H 0.6253 1.0542 0.2373 0.045 Uiso 0.511(5) 1 calc PR A 2 H16F H 0.5208 1.1125 0.1728 0.045 Uiso 0.511(5) 1 calc PR A 2 C18' C 0.1010(18) 1.0699(7) 0.1865(13) 0.0343(18) Uani 0.511(5) 1 d PU A 2 H18D H 0.1224 1.1110 0.2201 0.051 Uiso 0.511(5) 1 calc PR A 2 H18E H 0.0150 1.0498 0.2182 0.051 Uiso 0.511(5) 1 calc PR A 2 H18F H 0.0580 1.0724 0.0986 0.051 Uiso 0.511(5) 1 calc PR A 2 C17' C 0.3790(16) 1.0374(6) 0.3521(12) 0.0338(18) Uani 0.511(5) 1 d PU A 2 H17D H 0.4175 1.0795 0.3697 0.051 Uiso 0.511(5) 1 calc PR A 2 H17E H 0.4796 1.0106 0.3661 0.051 Uiso 0.511(5) 1 calc PR A 2 H17F H 0.3088 1.0252 0.4046 0.051 Uiso 0.511(5) 1 calc PR A 2 C15' C 0.2740(15) 1.0475(5) 0.0027(10) 0.0305(17) Uani 0.511(5) 1 d PU A 2 H15D H 0.1666 1.0240 -0.0170 0.046 Uiso 0.511(5) 1 calc PR A 2 H15E H 0.3399 1.0368 -0.0536 0.046 Uiso 0.511(5) 1 calc PR A 2 H15F H 0.2472 1.0910 -0.0037 0.046 Uiso 0.511(5) 1 calc PR A 2 O3 O 0.5844(6) 0.68761(16) 0.0461(4) 0.0488(11) Uani 1 1 d . A . O4 O 0.6441(6) 0.78111(16) -0.0058(4) 0.0443(10) Uani 1 1 d . A . C1 C 0.2391(6) 0.7639(2) 0.2180(5) 0.0265(10) Uani 1 1 d . A . C2 C 0.3449(6) 0.7366(2) 0.1587(5) 0.0284(10) Uani 1 1 d . . . H2 H 0.3497 0.6935 0.1539 0.034 Uiso 1 1 calc R . . C3 C 0.4447(6) 0.77273(19) 0.1060(4) 0.0252(10) Uani 1 1 d . A . C4 C 0.4325(6) 0.8357(2) 0.1126(4) 0.0264(10) Uani 1 1 d . . . H4 H 0.5000 0.8605 0.0761 0.032 Uiso 1 1 calc R A . C5 C 0.3238(6) 0.86354(19) 0.1713(4) 0.0227(9) Uani 1 1 d . A . C6 C 0.2256(6) 0.8270(2) 0.2278(4) 0.0223(9) Uani 1 1 d . . . C7 C 0.1188(7) 0.8550(2) 0.2990(5) 0.0281(10) Uani 1 1 d . A . C8 C 0.1953(8) 0.8793(3) 0.4096(5) 0.0465(15) Uani 1 1 d . . . H8 H 0.3167 0.8764 0.4425 0.056 Uiso 1 1 calc R A . C9 C 0.0974(10) 0.9083(4) 0.4748(6) 0.070(2) Uani 1 1 d . A . H9 H 0.1521 0.9241 0.5525 0.084 Uiso 1 1 calc R . . C10 C -0.0777(9) 0.9141(3) 0.4273(6) 0.0546(18) Uani 1 1 d . . . H10 H -0.1439 0.9342 0.4717 0.066 Uiso 1 1 calc R A . C11 C -0.1574(7) 0.8907(3) 0.3147(6) 0.0412(13) Uani 1 1 d . A . H11 H -0.2783 0.8951 0.2813 0.049 Uiso 1 1 calc R . . C12 C -0.0614(7) 0.8607(2) 0.2505(5) 0.0322(11) Uani 1 1 d . . . H12 H -0.1168 0.8440 0.1738 0.039 Uiso 1 1 calc R A . C19 C 0.5623(7) 0.7419(2) 0.0465(5) 0.0310(11) Uani 1 1 d . . . C20 C 0.7632(10) 0.7540(3) -0.0636(7) 0.060(2) Uani 1 1 d . . . H20A H 0.8548 0.7329 -0.0033 0.090 Uiso 1 1 calc R A . H20B H 0.8139 0.7859 -0.1019 0.090 Uiso 1 1 calc R . . H20C H 0.7016 0.7249 -0.1247 0.090 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 0.0503(3) 0.0233(2) 0.0694(4) 0.0084(3) 0.0383(3) -0.0051(2) B1 0.027(3) 0.021(2) 0.025(3) 0.002(2) 0.011(2) -0.001(2) O1 0.031(3) 0.019(2) 0.040(5) 0.004(4) 0.019(5) 0.003(2) O2 0.027(3) 0.015(2) 0.034(3) 0.001(3) 0.012(3) 0.001(2) C13 0.034(2) 0.0191(19) 0.030(2) -0.0025(19) 0.010(2) -0.0006(18) C14 0.035(2) 0.0195(19) 0.032(2) -0.003(2) 0.009(2) 0.0006(19) C15 0.037(4) 0.025(3) 0.035(3) 0.005(3) 0.007(3) 0.002(3) C17 0.035(4) 0.027(3) 0.028(3) -0.003(3) 0.008(3) -0.004(4) C16 0.035(3) 0.021(3) 0.031(4) -0.004(3) 0.011(3) -0.004(3) C18 0.036(4) 0.024(3) 0.036(4) -0.010(3) 0.004(3) 0.005(3) O1' 0.031(3) 0.019(2) 0.041(5) 0.003(4) 0.015(5) 0.002(2) O2' 0.027(3) 0.015(2) 0.031(3) 0.001(3) 0.014(3) 0.001(2) C13' 0.034(2) 0.0189(19) 0.031(2) -0.0019(19) 0.010(2) 0.0000(18) C14' 0.035(2) 0.0202(19) 0.032(2) -0.003(2) 0.010(2) 0.0008(19) C16' 0.037(3) 0.021(3) 0.033(4) -0.003(3) 0.011(3) -0.005(3) C18' 0.036(4) 0.025(3) 0.039(4) -0.010(3) 0.007(3) 0.005(3) C17' 0.042(4) 0.027(3) 0.031(3) -0.002(3) 0.009(3) 0.001(4) C15' 0.035(4) 0.025(3) 0.033(3) 0.007(3) 0.012(3) 0.004(4) O3 0.056(3) 0.0206(18) 0.085(3) -0.0053(19) 0.044(3) 0.0017(17) O4 0.065(3) 0.0252(18) 0.063(3) 0.0024(18) 0.051(2) 0.0028(18) C1 0.028(2) 0.019(2) 0.035(3) 0.0026(19) 0.014(2) -0.0041(18) C2 0.031(3) 0.015(2) 0.042(3) 0.0021(19) 0.015(2) -0.0023(18) C3 0.032(3) 0.017(2) 0.031(3) 0.0003(18) 0.016(2) -0.0007(18) C4 0.032(3) 0.018(2) 0.032(3) 0.0020(19) 0.015(2) -0.0029(19) C5 0.027(2) 0.018(2) 0.024(2) 0.0025(17) 0.0087(19) -0.0003(17) C6 0.021(2) 0.020(2) 0.027(2) 0.0025(17) 0.0068(19) -0.0005(17) C7 0.034(3) 0.020(2) 0.033(3) 0.006(2) 0.014(2) 0.000(2) C8 0.037(3) 0.061(4) 0.037(3) -0.009(3) 0.004(3) 0.020(3) C9 0.070(5) 0.098(6) 0.035(4) -0.017(4) 0.003(3) 0.037(5) C10 0.057(4) 0.065(4) 0.050(4) 0.000(3) 0.028(3) 0.026(3) C11 0.029(3) 0.045(3) 0.053(4) 0.007(3) 0.018(3) 0.007(2) C12 0.031(3) 0.030(3) 0.039(3) 0.002(2) 0.015(2) -0.002(2) C19 0.036(3) 0.019(2) 0.041(3) -0.002(2) 0.016(2) -0.003(2) C20 0.082(5) 0.042(3) 0.082(5) 0.003(3) 0.067(5) 0.007(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 1.911(4) . ? B1 O1' 1.307(11) . ? B1 O2' 1.364(8) . ? B1 O1 1.381(11) . ? B1 O2 1.389(9) . ? B1 C5 1.573(6) . ? O1 C14 1.559(14) . ? O2 C13 1.476(11) . ? C13 C16 1.49(2) . ? C13 C17 1.505(17) . ? C13 C14 1.544(15) . ? C14 C15 1.536(17) . ? C14 C18 1.564(19) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? O1' C14' 1.712(14) . ? O2' C13' 1.477(10) . ? C13' C15' 1.525(15) . ? C13' C16' 1.53(2) . ? C13' C14' 1.550(14) . ? C14' C17' 1.505(17) . ? C14' C18' 1.573(18) . ? C16' H16D 0.9800 . ? C16' H16E 0.9800 . ? C16' H16F 0.9800 . ? C18' H18D 0.9800 . ? C18' H18E 0.9800 . ? C18' H18F 0.9800 . ? C17' H17D 0.9800 . ? C17' H17E 0.9800 . ? C17' H17F 0.9800 . ? C15' H15D 0.9800 . ? C15' H15E 0.9800 . ? C15' H15F 0.9800 . ? O3 C19 1.207(6) . ? O4 C19 1.333(6) . ? O4 C20 1.448(6) . ? C1 C2 1.378(7) . ? C1 C6 1.398(6) . ? C2 C3 1.391(6) . ? C2 H2 0.9500 . ? C3 C4 1.393(6) . ? C3 C19 1.487(7) . ? C4 C5 1.395(6) . ? C4 H4 0.9500 . ? C5 C6 1.415(6) . ? C6 C7 1.485(7) . ? C7 C8 1.365(8) . ? C7 C12 1.412(7) . ? C8 C9 1.395(8) . ? C8 H8 0.9500 . ? C9 C10 1.374(10) . ? C9 H9 0.9500 . ? C10 C11 1.381(9) . ? C10 H10 0.9500 . ? C11 C12 1.384(7) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? 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 O1' B1 O2' 104.3(6) . . ? O1' B1 O1 28.8(4) . . ? O2' B1 O1 113.2(6) . . ? O1' B1 O2 115.3(6) . . ? O2' B1 O2 38.0(4) . . ? O1 B1 O2 104.6(6) . . ? O1' B1 C5 124.7(6) . . ? O2' B1 C5 120.1(5) . . ? O1 B1 C5 126.4(6) . . ? O2 B1 C5 120.0(5) . . ? B1 O1 C14 98.3(7) . . ? B1 O2 C13 105.5(6) . . ? O2 C13 C16 109.9(10) . . ? O2 C13 C17 106.2(9) . . ? C16 C13 C17 108.3(10) . . ? O2 C13 C14 101.7(7) . . ? C16 C13 C14 115.7(11) . . ? C17 C13 C14 114.4(9) . . ? C15 C14 C13 112.4(9) . . ? C15 C14 O1 133.5(9) . . ? C13 C14 O1 89.5(8) . . ? C15 C14 C18 111.0(10) . . ? C13 C14 C18 106.0(9) . . ? O1 C14 C18 100.6(10) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? B1 O1' C14' 96.6(7) . . ? B1 O2' C13' 107.6(6) . . ? O2' C13' C15' 105.9(8) . . ? O2' C13' C16' 107.0(10) . . ? C15' C13' C16' 109.7(10) . . ? O2' C13' C14' 102.0(7) . . ? C15' C13' C14' 113.5(9) . . ? C16' C13' C14' 117.5(9) . . ? C17' C14' C13' 114.5(9) . . ? C17' C14' C18' 116.1(10) . . ? C13' C14' C18' 116.1(10) . . ? C17' C14' O1' 126.2(9) . . ? C13' C14' O1' 85.9(7) . . ? C18' C14' O1' 93.8(8) . . ? C13' C16' H16D 109.5 . . ? C13' C16' H16E 109.5 . . ? H16D C16' H16E 109.5 . . ? C13' C16' H16F 109.5 . . ? H16D C16' H16F 109.5 . . ? H16E C16' H16F 109.5 . . ? C14' C18' H18D 109.5 . . ? C14' C18' H18E 109.5 . . ? H18D C18' H18E 109.5 . . ? C14' C18' H18F 109.5 . . ? H18D C18' H18F 109.5 . . ? H18E C18' H18F 109.5 . . ? C14' C17' H17D 109.5 . . ? C14' C17' H17E 109.5 . . ? H17D C17' H17E 109.5 . . ? C14' C17' H17F 109.5 . . ? H17D C17' H17F 109.5 . . ? H17E C17' H17F 109.5 . . ? C13' C15' H15D 109.5 . . ? C13' C15' H15E 109.5 . . ? H15D C15' H15E 109.5 . . ? C13' C15' H15F 109.5 . . ? H15D C15' H15F 109.5 . . ? H15E C15' H15F 109.5 . . ? C19 O4 C20 115.1(4) . . ? C2 C1 C6 123.2(4) . . ? C2 C1 Br1 116.5(3) . . ? C6 C1 Br1 120.2(4) . . ? C1 C2 C3 119.2(4) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C2 C3 C4 119.1(4) . . ? C2 C3 C19 118.0(4) . . ? C4 C3 C19 122.9(4) . . ? C3 C4 C5 121.8(4) . . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.1 . . ? C4 C5 C6 119.4(4) . . ? C4 C5 B1 118.2(4) . . ? C6 C5 B1 122.5(4) . . ? C1 C6 C5 117.3(4) . . ? C1 C6 C7 121.8(4) . . ? C5 C6 C7 120.8(4) . . ? C8 C7 C12 118.8(5) . . ? C8 C7 C6 120.2(5) . . ? C12 C7 C6 120.9(5) . . ? C7 C8 C9 120.8(6) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C10 C9 C8 120.3(6) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 119.9(6) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C12 120.1(5) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C7 120.1(5) . . ? C11 C12 H12 119.9 . . ? C7 C12 H12 119.9 . . ? O3 C19 O4 123.1(5) . . ? O3 C19 C3 124.6(5) . . ? O4 C19 C3 112.3(4) . . ? O4 C20 H20A 109.5 . . ? O4 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O4 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.435 _refine_diff_density_min -0.808 _refine_diff_density_rms 0.100