# 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_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_address ; Early Development, Solid State & Physical Chemistry/SBBG, B341:3, PAR&D M/S, AstraZeneca R&D, S-151 58 S\"odert\"alje, Sweden ; ; Pharmaceutical Development, AstraZeneca R&D Charnwood, Bakewell Road, Loughborough LE12 7GN, UK. Tel: +44(0)1509647363.Fax: +44(0)645588. E- ; ; Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK. ; ; Pharmaceutical Development, AstraZeneca R&D Charnwood, Bakewell Road, Loughborough LE12 7GN, UK. Tel: +44(0)1509647363. Fax: +44(0)645588. E- ; ; Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK ; ; Pharmaceutical Development, AstraZeneca R&D Charnwood, Bakewell Road, Loughborough LE12 7GN, UK. Tel: +44(0)1509647363.Fax: +44(0)645588. E- ; _publ_contact_author_address ; Medicines Evaluation, Phmarmaceutical Development, B341:3,, AstraZeneca R&D, S-151 58 S\"odert\"alje, Sweden ; _publ_contact_author_email Per.h.svensson@astrazeneca.com _publ_contact_author_fax '+46 8 553 289 07 ' _publ_contact_author_phone '+46 8 553 210 36 ' _publ_contact_author_name 'Per H. Svensson' #=============================================================================== #============================================================================== _publ_section_title ; Crystal and molecular structure ; loop_ _publ_author_name W.J.Kerr D.Gill # Attachment 'Benzyl-7-benzyl-8-(2-bromophenyl)-2-methoxy- #9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate.cif' #CIF-file for Benzyl-7-benzyl-8-(2-bromophenyl)-2-methoxy- #9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate #============================================================================== data_2 _database_code_depnum_ccdc_archive 'CCDC 835119' #Benzyl-7-benzyl-8-(2-bromophenyl)-2-methoxy-9-oxa- #3,7-diazabicyclo[3.3.1]nonane-3-carboxylate #TrackingRef 'Benzyl-7-benzyl-8-(2-bromophenyl)-2-methoxy- #9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate.cif' #============================================================================== _audit_creation_method 'maXus and PLATON' _publ_section_abstract ; ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All diagrams and calculations were performed using maXus (Bruker Nonius, Delft & MacScience, Japan). ; _publ_section_synopsis ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; _chemical_compound_source 'Local laboratory' _exptl_crystal_description 'Prismatic block' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _cell_measurement_temperature 298 _refine_ls_hydrogen_treatment constr _exptl_crystal_F_000 1112 _chemical_absolute_configuration ad _diffrn_measurement_device KappaCCD _computing_data_collection KappaCCD _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type X=UH _diffrn_orient_matrix_UB_11 -0.05941 _diffrn_orient_matrix_UB_12 0.00179 _diffrn_orient_matrix_UB_13 -0.04011 _diffrn_orient_matrix_UB_21 -0.11570 _diffrn_orient_matrix_UB_22 0.00158 _diffrn_orient_matrix_UB_23 0.02062 _diffrn_orient_matrix_UB_31 0.00440 _diffrn_orient_matrix_UB_32 0.06572 _diffrn_orient_matrix_UB_33 0.00060 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 537.43 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z '-X+ 1/2,-Y,+Z+ 1/2' '+X+ 1/2,-Y+ 1/2,-Z' '-X,+Y+ 1/2,-Z+ 1/2' _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_cell_setting Orthorhombic _chemical_formula_moiety 'C28 H29 Br N2 O4 ' _chemical_formula_sum 'C28 H29 Br N2 O4 ' _chemical_name_systematic ; (13S,16R,17R,18R)-benzyl-7-benzyl-8-(2-bromophenyl) -2-methoxy-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate. ; _cell_length_a 7.68450(10) _cell_length_b 15.2060(4) _cell_length_c 22.1725(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2590.87(10) _diffrn_reflns_number 5793 _diffrn_reflns_theta_max 27.46 _diffrn_reflns_theta_min 0.92 _diffrn_reflns_theta_full 27.46 _cell_measurement_reflns_used 3232 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 27.485 _diffrn_measurement_method CCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _exptl_absorpt_coefficient_mu 1.620 _reflns_number_total 5766 _reflns_number_gt 3706 _reflns_threshold_expression >2sigma(I) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0589P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _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 0.018(9) _refine_ls_number_reflns 5766 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0642 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.1015 _refine_ls_wR_factor_gt 0.0794 _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_restrained_S_all 0.963 _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 C1 C 0.3360(6) 0.8667(3) 0.3130(2) 0.0896(13) Uani 1 1 d . . . C2 C 0.3544(8) 0.8738(4) 0.2510(2) 0.1183(19) Uani 1 1 d . . . C3 C 0.3497(6) 0.9535(5) 0.2246(2) 0.1061(16) Uani 1 1 d . . . C4 C 0.3237(6) 1.0275(4) 0.2582(2) 0.1027(15) Uani 1 1 d . . . C5 C 0.2991(6) 1.0193(3) 0.3186(2) 0.0839(12) Uani 1 1 d . . . C6 C 0.3062(4) 0.9393(2) 0.34737(15) 0.0567(8) Uani 1 1 d . . . C7 C 0.2832(4) 0.9325(3) 0.41360(17) 0.0661(10) Uani 1 1 d . . . C9 C 0.5559(4) 0.8905(2) 0.45673(14) 0.0489(7) Uani 1 1 d . . . C12 C 0.8489(4) 0.8578(2) 0.49109(15) 0.0536(8) Uani 1 1 d . . . C13 C 0.9478(4) 0.89003(19) 0.54569(16) 0.0550(8) Uani 1 1 d . . . C14 C 0.8468(4) 0.8899(2) 0.60377(15) 0.0580(8) Uani 1 1 d . . . C16 C 0.7694(4) 1.04155(19) 0.58751(15) 0.0498(7) Uani 1 1 d . . . C17 C 0.8722(4) 1.03607(17) 0.52801(15) 0.0480(7) Uani 1 1 d . . . C18 C 0.7657(4) 1.01192(18) 0.47238(15) 0.0471(7) Uani 1 1 d . . . C20 C 0.8007(6) 1.0189(3) 0.36556(17) 0.0834(12) Uani 1 1 d . . . C22 C 0.6266(5) 0.9550(2) 0.66590(15) 0.0631(8) Uani 1 1 d . . . C23 C 0.5295(5) 0.8713(2) 0.67999(16) 0.0593(8) Uani 1 1 d . . . C24 C 0.4043(5) 0.8389(2) 0.64188(18) 0.0724(10) Uani 1 1 d . . . C25 C 0.3082(5) 0.7655(3) 0.6564(2) 0.0874(12) Uani 1 1 d . . . C26 C 0.3360(6) 0.7233(3) 0.7098(2) 0.0919(13) Uani 1 1 d . . . C27 C 0.4625(6) 0.7536(3) 0.74856(19) 0.0896(12) Uani 1 1 d . . . C28 C 0.5594(6) 0.8270(2) 0.73347(17) 0.0737(10) Uani 1 1 d . . . C29 C 0.6257(4) 1.11027(18) 0.58197(14) 0.0487(7) Uani 1 1 d . . . C30 C 0.4587(4) 1.0863(2) 0.56635(16) 0.0575(8) Uani 1 1 d . . . C31 C 0.3287(4) 1.1487(2) 0.55822(17) 0.0664(9) Uani 1 1 d . . . C32 C 0.3676(4) 1.2370(2) 0.56546(17) 0.0683(9) Uani 1 1 d . . . C33 C 0.5322(4) 1.2633(2) 0.58112(16) 0.0605(8) Uani 1 1 d . . . C34 C 0.6591(4) 1.1998(2) 0.58912(14) 0.0502(7) Uani 1 1 d . . . N11 N 0.7143(3) 0.92067(14) 0.47411(12) 0.0457(6) Uani 1 1 d . . . N15 N 0.7027(3) 0.95407(15) 0.60481(12) 0.0509(6) Uani 1 1 d . . . O8 O 0.4465(3) 0.95679(15) 0.44379(10) 0.0588(6) Uani 1 1 d . . . O10 O 0.5169(3) 0.81357(15) 0.45431(12) 0.0696(7) Uani 1 1 d . . . O19 O 0.8788(3) 1.02952(13) 0.42246(10) 0.0571(5) Uani 1 1 d . . . O21 O 1.0166(2) 0.97692(13) 0.53430(11) 0.0564(5) Uani 1 1 d . . . Br35 Br 0.88466(4) 1.24121(2) 0.610864(19) 0.07047(14) Uani 1 1 d . . . H1 H 0.3440 0.8117 0.3312 0.108 Uiso 1 1 calc R . . H2 H 0.3701 0.8236 0.2276 0.142 Uiso 1 1 calc R . . H3 H 0.3642 0.9582 0.1831 0.127 Uiso 1 1 calc R . . H4 H 0.3228 1.0827 0.2401 0.123 Uiso 1 1 calc R . . H5 H 0.2767 1.0695 0.3413 0.101 Uiso 1 1 calc R . . H7A H 0.1905 0.9714 0.4266 0.079 Uiso 1 1 calc R . . H7B H 0.2514 0.8728 0.4244 0.079 Uiso 1 1 calc R . . H12A H 0.9287 0.8498 0.4577 0.064 Uiso 1 1 calc R . . H12B H 0.7958 0.8014 0.5000 0.064 Uiso 1 1 calc R . . H13 H 1.0474 0.8506 0.5512 0.066 Uiso 1 1 calc R . . H14A H 0.7998 0.8315 0.6104 0.070 Uiso 1 1 calc R . . H14B H 0.9257 0.9029 0.6367 0.070 Uiso 1 1 calc R . . H16 H 0.8497 1.0611 0.6191 0.060 Uiso 1 1 calc R . . H17 H 0.9211 1.0946 0.5207 0.058 Uiso 1 1 calc R . . H18 H 0.6623 1.0495 0.4699 0.057 Uiso 1 1 calc R . . H20A H 0.8843 1.0314 0.3346 0.125 Uiso 1 1 calc R . . H20B H 0.7040 1.0586 0.3619 0.125 Uiso 1 1 calc R . . H20C H 0.7603 0.9595 0.3613 0.125 Uiso 1 1 calc R . . H22A H 0.5475 1.0045 0.6693 0.076 Uiso 1 1 calc R . . H22B H 0.7188 0.9630 0.6953 0.076 Uiso 1 1 calc R . . H24 H 0.3839 0.8672 0.6054 0.087 Uiso 1 1 calc R . . H25 H 0.2242 0.7447 0.6298 0.105 Uiso 1 1 calc R . . H26 H 0.2699 0.6742 0.7200 0.110 Uiso 1 1 calc R . . H27 H 0.4828 0.7248 0.7849 0.108 Uiso 1 1 calc R . . H28 H 0.6457 0.8468 0.7596 0.088 Uiso 1 1 calc R . . H30 H 0.4325 1.0271 0.5611 0.069 Uiso 1 1 calc R . . H31 H 0.2165 1.1313 0.5480 0.080 Uiso 1 1 calc R . . H32 H 0.2811 1.2789 0.5596 0.082 Uiso 1 1 calc R . . H33 H 0.5580 1.3226 0.5863 0.073 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 C1 0.118(4) 0.070(3) 0.081(3) -0.009(2) 0.012(3) -0.011(2) C2 0.142(5) 0.115(4) 0.098(4) -0.033(3) 0.029(4) -0.017(4) C3 0.089(3) 0.157(5) 0.071(3) 0.011(3) 0.002(3) -0.019(4) C4 0.097(3) 0.107(4) 0.105(4) 0.033(3) -0.010(3) 0.003(3) C5 0.087(3) 0.075(3) 0.090(3) -0.001(2) -0.008(2) 0.014(2) C6 0.0421(15) 0.061(2) 0.067(2) -0.0044(18) -0.0027(16) -0.0027(14) C7 0.0421(17) 0.079(3) 0.077(3) -0.015(2) -0.0029(17) -0.0037(16) C9 0.0520(16) 0.0452(18) 0.0494(18) 0.0013(14) 0.0072(14) -0.0044(14) C12 0.0537(18) 0.0361(16) 0.071(2) -0.0006(14) 0.0001(16) 0.0046(13) C13 0.0543(17) 0.0350(15) 0.076(2) -0.0010(15) -0.0075(17) 0.0079(13) C14 0.0652(19) 0.0431(16) 0.066(2) 0.0007(15) -0.0106(18) 0.0084(13) C16 0.0496(16) 0.0378(15) 0.062(2) -0.0034(14) -0.0034(15) 0.0010(13) C17 0.0410(14) 0.0323(13) 0.0707(19) -0.0021(13) -0.0006(16) 0.0020(13) C18 0.0461(15) 0.0333(15) 0.062(2) 0.0028(14) 0.0027(15) -0.0021(12) C20 0.087(3) 0.097(3) 0.066(3) 0.010(2) 0.005(2) -0.019(2) C22 0.079(2) 0.0520(18) 0.059(2) -0.0041(15) 0.001(2) -0.0050(19) C23 0.071(2) 0.0548(19) 0.052(2) -0.0041(16) 0.0086(17) -0.0018(16) C24 0.086(2) 0.068(2) 0.064(2) 0.0023(18) -0.005(2) -0.012(2) C25 0.095(3) 0.082(3) 0.086(3) -0.011(2) 0.003(2) -0.025(2) C26 0.112(3) 0.066(3) 0.098(3) 0.000(2) 0.027(3) -0.020(2) C27 0.118(3) 0.082(3) 0.069(2) 0.017(2) 0.013(2) -0.011(3) C28 0.092(3) 0.065(2) 0.065(2) 0.0030(19) 0.001(2) -0.001(2) C29 0.0485(15) 0.0409(15) 0.0567(17) -0.0046(13) -0.0015(16) 0.0021(14) C30 0.0541(16) 0.0451(17) 0.073(2) -0.0029(16) 0.0019(17) -0.0001(15) C31 0.0478(17) 0.067(2) 0.084(2) 0.0000(19) -0.0019(17) 0.0050(16) C32 0.0617(19) 0.0560(19) 0.087(2) 0.0043(18) -0.0006(18) 0.017(2) C33 0.0637(18) 0.0429(18) 0.075(2) -0.0020(16) 0.0015(17) 0.0081(16) C34 0.0499(16) 0.0429(16) 0.0579(19) -0.0060(14) 0.0004(14) 0.0006(13) N11 0.0462(13) 0.0303(12) 0.0604(16) 0.0004(11) 0.0008(13) -0.0037(10) N15 0.0577(14) 0.0367(12) 0.0584(16) -0.0018(12) 0.0034(14) 0.0018(10) O8 0.0480(11) 0.0544(13) 0.0740(15) -0.0109(11) -0.0057(11) 0.0012(10) O10 0.0691(14) 0.0438(13) 0.0961(19) -0.0019(12) 0.0004(13) -0.0170(11) O19 0.0577(11) 0.0497(11) 0.0639(14) 0.0058(10) 0.0092(12) -0.0069(11) O21 0.0443(10) 0.0425(12) 0.0824(16) -0.0033(11) -0.0043(11) 0.0049(9) Br35 0.06214(19) 0.04889(18) 0.1004(3) -0.01667(18) -0.01174(18) -0.00338(16) # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br35 C34 1.906(3) . . yes O8 C7 1.470(4) . . yes O8 C9 1.344(4) . . yes O10 C9 1.209(4) . . yes O19 C18 1.433(4) . . yes O19 C20 1.406(5) . . yes O21 C13 1.445(4) . . yes O21 C17 1.435(3) . . yes N11 C9 1.357(4) . . yes N11 C12 1.458(4) . . yes N11 C18 1.443(3) . . yes N15 C14 1.476(4) . . yes N15 C16 1.476(4) . . yes N15 C22 1.476(4) . . yes C1 C2 1.386(6) . . no C1 C6 1.361(6) . . no C2 C3 1.346(9) . . no C3 C4 1.364(9) . . no C4 C5 1.358(6) . . no C5 C6 1.375(5) . . no C6 C7 1.483(5) . . no C12 C13 1.511(5) . . no C13 C14 1.504(5) . . no C16 C17 1.540(5) . . no C16 C29 1.525(4) . . no C17 C18 1.525(5) . . no C22 C23 1.508(5) . . no C23 C24 1.372(5) . . no C23 C28 1.383(5) . . no C24 C25 1.377(5) . . no C25 C26 1.364(6) . . no C26 C27 1.377(6) . . no C27 C28 1.383(6) . . no C29 C30 1.378(4) . . no C29 C34 1.394(4) . . no C30 C31 1.390(4) . . no C31 C32 1.385(4) . . no C32 C33 1.371(4) . . no C33 C34 1.384(4) . . no C1 H1 0.9306 . . no C2 H2 0.9308 . . no C3 H3 0.9297 . . no C4 H4 0.9304 . . no C5 H5 0.9304 . . no C7 H7A 0.9698 . . no C7 H7B 0.9701 . . no C12 H12A 0.9690 . . no C12 H12B 0.9701 . . no C13 H13 0.9799 . . no C14 H14A 0.9699 . . no C14 H14B 0.9695 . . no C16 H16 0.9797 . . no C17 H17 0.9796 . . no C18 H18 0.9803 . . no C20 H20A 0.9592 . . no C20 H20B 0.9609 . . no C20 H20C 0.9598 . . no C22 H22A 0.9704 . . no C22 H22B 0.9705 . . no C24 H24 0.9295 . . no C25 H25 0.9299 . . no C26 H26 0.9309 . . no C27 H27 0.9303 . . no C28 H28 0.9307 . . no C30 H30 0.9298 . . no C31 H31 0.9300 . . no C32 H32 0.9299 . . no C33 H33 0.9304 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O8 C9 116.3(3) . . . yes C18 O19 C20 114.4(3) . . . yes C13 O21 C17 107.88(19) . . . yes C9 N11 C12 119.2(2) . . . yes C9 N11 C18 124.3(2) . . . yes C12 N11 C18 116.3(2) . . . yes C14 N15 C16 109.3(2) . . . yes C14 N15 C22 108.5(2) . . . yes C16 N15 C22 111.6(2) . . . yes C2 C1 C6 120.6(4) . . . no C1 C2 C3 119.9(5) . . . no C2 C3 C4 120.6(4) . . . no C3 C4 C5 118.9(5) . . . no C4 C5 C6 122.2(4) . . . no C1 C6 C5 117.7(4) . . . no C1 C6 C7 121.2(3) . . . no C5 C6 C7 121.1(3) . . . no O8 C7 C6 109.4(3) . . . yes O8 C9 O10 124.2(3) . . . yes O8 C9 N11 111.6(3) . . . yes O10 C9 N11 124.2(3) . . . yes N11 C12 C13 110.6(2) . . . yes O21 C13 C12 109.9(3) . . . yes O21 C13 C14 109.9(2) . . . yes C12 C13 C14 115.2(3) . . . no N15 C14 C13 113.6(3) . . . yes N15 C16 C17 110.6(2) . . . yes N15 C16 C29 112.8(2) . . . yes C17 C16 C29 109.9(3) . . . no O21 C17 C16 110.3(2) . . . yes O21 C17 C18 110.0(2) . . . yes C16 C17 C18 115.5(3) . . . no O19 C18 N11 111.5(2) . . . yes O19 C18 C17 104.7(2) . . . yes N11 C18 C17 110.9(2) . . . yes N15 C22 C23 112.2(3) . . . yes C22 C23 C24 121.5(3) . . . no C22 C23 C28 120.4(3) . . . no C24 C23 C28 118.0(3) . . . no C23 C24 C25 121.6(4) . . . no C24 C25 C26 120.0(4) . . . no C25 C26 C27 119.7(4) . . . no C26 C27 C28 120.0(4) . . . no C23 C28 C27 120.7(4) . . . no C16 C29 C30 120.9(3) . . . no C16 C29 C34 121.8(3) . . . no C30 C29 C34 117.3(3) . . . no C29 C30 C31 121.4(3) . . . no C30 C31 C32 119.5(3) . . . no C31 C32 C33 120.7(3) . . . no C32 C33 C34 118.6(3) . . . no Br35 C34 C29 121.2(2) . . . yes Br35 C34 C33 116.3(2) . . . yes C29 C34 C33 122.5(3) . . . no C2 C1 H1 119.56 . . . no C6 C1 H1 119.82 . . . no C1 C2 H2 120.14 . . . no C3 C2 H2 119.95 . . . no C2 C3 H3 119.76 . . . no C4 C3 H3 119.65 . . . no C3 C4 H4 120.64 . . . no C5 C4 H4 120.47 . . . no C4 C5 H5 118.94 . . . no C6 C5 H5 118.84 . . . no O8 C7 H7A 109.79 . . . no O8 C7 H7B 109.75 . . . no C6 C7 H7A 109.84 . . . no C6 C7 H7B 109.86 . . . no H7A C7 H7B 108.20 . . . no N11 C12 H12A 109.51 . . . no N11 C12 H12B 109.50 . . . no C13 C12 H12A 109.54 . . . no C13 C12 H12B 109.58 . . . no H12A C12 H12B 108.11 . . . no O21 C13 H13 107.18 . . . no C12 C13 H13 107.12 . . . no C14 C13 H13 107.19 . . . no N15 C14 H14A 108.87 . . . no N15 C14 H14B 108.82 . . . no C13 C14 H14A 108.86 . . . no C13 C14 H14B 108.78 . . . no H14A C14 H14B 107.79 . . . no N15 C16 H16 107.84 . . . no C17 C16 H16 107.80 . . . no C29 C16 H16 107.80 . . . no O21 C17 H17 106.79 . . . no C16 C17 H17 106.82 . . . no C18 C17 H17 106.91 . . . no O19 C18 H18 109.85 . . . no N11 C18 H18 109.88 . . . no C17 C18 H18 109.88 . . . no O19 C20 H20A 109.47 . . . no O19 C20 H20B 109.49 . . . no O19 C20 H20C 109.54 . . . no H20A C20 H20B 109.46 . . . no H20A C20 H20C 109.43 . . . no H20B C20 H20C 109.44 . . . no N15 C22 H22A 109.09 . . . no N15 C22 H22B 109.18 . . . no C23 C22 H22A 109.18 . . . no C23 C22 H22B 109.14 . . . no H22A C22 H22B 107.94 . . . no C23 C24 H24 119.21 . . . no C25 C24 H24 119.24 . . . no C24 C25 H25 119.99 . . . no C26 C25 H25 119.97 . . . no C25 C26 H26 120.19 . . . no C27 C26 H26 120.13 . . . no C26 C27 H27 120.10 . . . no C28 C27 H27 119.95 . . . no C23 C28 H28 119.64 . . . no C27 C28 H28 119.62 . . . no C29 C30 H30 119.28 . . . no C31 C30 H30 119.29 . . . no C30 C31 H31 120.26 . . . no C32 C31 H31 120.28 . . . no C31 C32 H32 119.59 . . . no C33 C32 H32 119.67 . . . no C32 C33 H33 120.70 . . . no C34 C33 H33 120.68 . . . no 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 C9 O8 C7 C6 -92.9(4) . . . . no C7 O8 C9 O10 -12.6(4) . . . . no C7 O8 C9 N11 168.7(3) . . . . no C20 O19 C18 C17 -174.7(3) . . . . no C20 O19 C18 N11 65.3(3) . . . . no C13 O21 C17 C18 -64.8(3) . . . . no C17 O21 C13 C12 65.7(3) . . . . no C13 O21 C17 C16 63.8(3) . . . . no C17 O21 C13 C14 -62.1(3) . . . . no C12 N11 C18 C17 -45.2(4) . . . . no C9 N11 C18 C17 140.0(3) . . . . no C18 N11 C12 C13 45.9(4) . . . . no C9 N11 C12 C13 -139.0(3) . . . . no C12 N11 C18 O19 71.1(3) . . . . no C9 N11 C18 O19 -103.7(3) . . . . no C18 N11 C9 O10 174.8(3) . . . . no C12 N11 C9 O10 0.2(5) . . . . no C18 N11 C9 O8 -6.6(4) . . . . no C12 N11 C9 O8 178.8(3) . . . . no C16 N15 C22 C23 169.7(3) . . . . no C14 N15 C22 C23 -69.8(3) . . . . no C14 N15 C16 C17 51.4(3) . . . . no C22 N15 C16 C17 171.5(3) . . . . no C14 N15 C16 C29 174.9(3) . . . . no C22 N15 C14 C13 -173.7(3) . . . . no C16 N15 C14 C13 -51.8(3) . . . . no C22 N15 C16 C29 -65.1(3) . . . . no C2 C1 C6 C5 -1.4(6) . . . . no C2 C1 C6 C7 178.9(4) . . . . no C6 C1 C2 C3 2.6(8) . . . . no C1 C2 C3 C4 -1.2(8) . . . . no C2 C3 C4 C5 -1.3(7) . . . . no C3 C4 C5 C6 2.6(7) . . . . no C4 C5 C6 C1 -1.2(6) . . . . no C4 C5 C6 C7 178.5(4) . . . . no C5 C6 C7 O8 -79.4(4) . . . . no C1 C6 C7 O8 100.2(4) . . . . no N11 C12 C13 O21 -55.0(3) . . . . no N11 C12 C13 C14 69.7(3) . . . . no C12 C13 C14 N15 -67.2(3) . . . . no O21 C13 C14 N15 57.5(3) . . . . no C17 C16 C29 C30 95.3(3) . . . . no C17 C16 C29 C34 -81.2(4) . . . . no N15 C16 C29 C30 -28.6(4) . . . . no N15 C16 C17 C18 65.9(3) . . . . no C29 C16 C17 C18 -59.2(3) . . . . no N15 C16 C29 C34 155.0(3) . . . . no N15 C16 C17 O21 -59.6(3) . . . . no C29 C16 C17 O21 175.3(2) . . . . no C16 C17 C18 N11 -71.7(3) . . . . no C16 C17 C18 O19 167.9(2) . . . . no O21 C17 C18 N11 54.0(3) . . . . no O21 C17 C18 O19 -66.4(3) . . . . no N15 C22 C23 C24 -51.8(5) . . . . no N15 C22 C23 C28 131.1(3) . . . . no C22 C23 C28 C27 175.6(4) . . . . no C28 C23 C24 C25 1.2(6) . . . . no C22 C23 C24 C25 -176.0(4) . . . . no C24 C23 C28 C27 -1.6(6) . . . . no C23 C24 C25 C26 0.2(6) . . . . no C24 C25 C26 C27 -1.1(7) . . . . no C25 C26 C27 C28 0.6(7) . . . . no C26 C27 C28 C23 0.8(6) . . . . no C30 C29 C34 Br35 179.8(2) . . . . no C30 C29 C34 C33 0.0(5) . . . . no C16 C29 C34 C33 176.5(3) . . . . no C16 C29 C34 Br35 -3.6(4) . . . . no C34 C29 C30 C31 -0.2(5) . . . . no C16 C29 C30 C31 -176.8(3) . . . . no C29 C30 C31 C32 0.5(5) . . . . no C30 C31 C32 C33 -0.7(6) . . . . no C31 C32 C33 C34 0.5(5) . . . . no C32 C33 C34 C29 -0.1(5) . . . . no C32 C33 C34 Br35 -180.0(3) . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Br35 C17 3.621(3) . . no Br35 H16 2.7580 . . no Br35 H17 3.0075 . . no Br35 H5 3.1778 . 3_576 no O8 C20 3.363(5) . . no O8 C30 3.357(4) . . no O10 C12 3.150(4) . 3_466 no O10 C13 3.141(4) . 3_466 no O19 C33 3.365(4) . 3_576 no O19 O21 2.813(3) . . no O21 N11 2.813(3) . . no O21 N15 2.896(3) . . no O21 O19 2.813(3) . . no O8 H30 2.8143 . . no O8 H18 2.2523 . . no O10 H12B 2.3779 . . no O10 H7B 2.3268 . . no O10 H13 2.5103 . 3_466 no O10 H12B 2.6400 . 3_466 no O10 H25 2.6079 . 3_566 no O19 H7A 2.5549 . 1_655 no O19 H12A 2.8681 . . no O19 H33 2.6440 . 3_576 no O21 H7A 2.7378 . 1_655 no O21 H31 2.8219 . 1_655 no N11 O21 2.813(3) . . no N11 N15 2.944(4) . . no N15 O21 2.896(3) . . no N15 N11 2.944(4) . . no N11 H20C 2.5943 . . no N15 H24 2.7834 . . no N15 H30 2.5464 . . no C2 C27 3.581(8) . 3_466 no C4 C23 3.570(6) . 2_574 no C9 C20 3.382(5) . . no C12 O10 3.150(4) . 3_566 no C12 C16 3.571(4) . . no C13 O10 3.141(4) . 3_566 no C14 C24 3.589(5) . . no C14 C18 3.510(5) . . no C16 C12 3.571(4) . . no C17 Br35 3.621(3) . . no C18 C14 3.510(5) . . no C18 C30 3.345(5) . . no C20 O8 3.363(5) . . no C20 C9 3.382(5) . . no C22 C30 3.244(5) . . no C23 C4 3.570(6) . 2_575 no C24 C14 3.589(5) . . no C27 C2 3.581(8) . 3_566 no C30 O8 3.357(4) . . no C30 C18 3.345(5) . . no C30 C22 3.244(5) . . no C33 O19 3.365(4) . 3_476 no C9 H25 3.0952 . 3_566 no C9 H20C 2.8365 . . no C17 H31 3.0487 . 1_655 no C22 H30 2.9710 . . no C23 H14A 2.6575 . . no C23 H4 3.0977 . 2_575 no C24 H4 3.0348 . 2_575 no C29 H22A 2.5879 . . no C29 H18 2.6661 . . no C30 H18 2.7083 . . no C30 H22A 2.6877 . . no C33 H27 3.0301 . 4_656 no C34 H17 2.9857 . . no C34 H27 3.0227 . 4_656 no H1 H7B 2.3749 . . no H1 H14A 2.5561 . 3_466 no H4 C23 3.0977 . 2_574 no H4 C24 3.0348 . 2_574 no H5 H7A 2.4983 . . no H5 Br35 3.1778 . 3_476 no H7A O19 2.5549 . 1_455 no H7A O21 2.7378 . 1_455 no H7A H5 2.4983 . . no H7B O10 2.3268 . . no H7B H1 2.3749 . . no H12A O19 2.8681 . . no H12B O10 2.3779 . . no H12B H14A 2.4905 . . no H12B O10 2.6400 . 3_566 no H13 O10 2.5103 . 3_566 no H14A C23 2.6575 . . no H14A H12B 2.4905 . . no H14A H1 2.5561 . 3_566 no H14B H16 2.5060 . . no H14B H22B 2.2476 . . no H16 Br35 2.7580 . . no H16 H14B 2.5060 . . no H16 H22B 2.4682 . . no H17 Br35 3.0075 . . no H17 C34 2.9857 . . no H17 H31 2.4148 . 1_655 no H18 O8 2.2523 . . no H18 C29 2.6661 . . no H18 C30 2.7083 . . no H18 H20B 2.4200 . . no H20A H28 2.4998 . 2_674 no H20B H18 2.4200 . . no H20C N11 2.5943 . . no H20C C9 2.8365 . . no H22A C29 2.5879 . . no H22A C30 2.6877 . . no H22A H30 2.5797 . . no H22B H14B 2.2476 . . no H22B H16 2.4682 . . no H22B H28 2.3389 . . no H24 N15 2.7834 . . no H25 O10 2.6079 . 3_466 no H25 C9 3.0952 . 3_466 no H27 C33 3.0301 . 4_646 no H27 C34 3.0227 . 4_646 no H28 H22B 2.3389 . . no H28 H20A 2.4998 . 2_675 no H30 O8 2.8143 . . no H30 N15 2.5464 . . no H30 C22 2.9710 . . no H30 H22A 2.5797 . . no H31 O21 2.8219 . 1_455 no H31 C17 3.0487 . 1_455 no H31 H17 2.4148 . 1_455 no H33 O19 2.6440 . 3_476 no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # C7 H7A O19 0.9700 2.5500 3.446(4) 153.00 1_455 yes C7 H7B O10 0.9700 2.3300 2.704(5) 102.00 . yes C12 H12B O10 0.9700 2.3800 2.762(4) 103.00 . yes C13 H13 O10 0.9800 2.5100 3.141(4) 122.00 3_566 yes C16 H16 Br35 0.9800 2.7600 3.205(3) 108.00 . yes C18 H18 O8 0.9800 2.2500 2.669(4) 104.00 . yes C30 H30 N15 0.9300 2.5500 2.879(4) 101.00 . yes _diffrn_measured_fraction_theta_max 0.993 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.328 _refine_diff_density_min -0.424 _refine_diff_density_rms 0.177 _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Sheldrick, G. M. (1997). SHELXL97. Program for the Refinement of Crystal Structures. University of G\"ottingen, Germany. ;