# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_sh2998 _database_code_depnum_ccdc_archive 'CCDC 831581' #TrackingRef 'web_deposit_cif_file_0_HardeshK.Maurya_1324060683.4. #X-Ray 17a (sh2998).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H24 N2 O3 S' _chemical_formula_weight 456.54 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' S S 0.1246 0.1234 '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 7.7227(6) _cell_length_b 11.4586(9) _cell_length_c 13.0552(11) _cell_angle_alpha 78.782(4) _cell_angle_beta 81.895(4) _cell_angle_gamma 80.857(4) _cell_volume 1111.55(15) _cell_formula_units_Z 2 _cell_measurement_temperature 132(2) _cell_measurement_reflns_used 4730 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 26.36 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 1.364 _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.179 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9094 _exptl_absorpt_correction_T_max 0.9911 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 132(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15809 _diffrn_reflns_av_R_equivalents 0.0949 _diffrn_reflns_av_sigmaI/netI 0.0919 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 26.40 _reflns_number_total 4535 _reflns_number_gt 3379 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0700P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4535 _refine_ls_number_parameters 394 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0929 _refine_ls_R_factor_gt 0.0653 _refine_ls_wR_factor_ref 0.1666 _refine_ls_wR_factor_gt 0.1539 _refine_ls_goodness_of_fit_ref 1.181 _refine_ls_restrained_S_all 1.181 _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 S1 S 1.25548(9) 0.73090(7) 0.50864(5) 0.0198(2) Uani 1 1 d . . . O1 O 0.9910(3) 0.95314(18) 0.86375(15) 0.0237(5) Uani 1 1 d . . . O2 O 1.4004(3) 0.20729(18) 0.84892(16) 0.0264(5) Uani 1 1 d . . . O3 O 0.6095(2) 0.54973(19) 0.63287(15) 0.0247(5) Uani 1 1 d . . . N1 N 0.7234(3) 0.4356(2) 0.97090(19) 0.0274(6) Uani 1 1 d . . . N2 N 1.1620(3) 0.4100(2) 0.77446(17) 0.0150(5) Uani 1 1 d . . . C1 C 0.7747(3) 0.6457(2) 0.72811(19) 0.0120(6) Uani 1 1 d . . . C2 C 0.8733(3) 0.5369(2) 0.79508(19) 0.0124(6) Uani 1 1 d . . . C3 C 1.0307(3) 0.4986(2) 0.74110(19) 0.0121(6) Uani 1 1 d . . . C4 C 1.0504(3) 0.5798(2) 0.6388(2) 0.0128(6) Uani 1 1 d . . . C5 C 1.2084(4) 0.5783(3) 0.5573(2) 0.0156(6) Uani 1 1 d . . . C6 C 1.0428(4) 0.8030(2) 0.4829(2) 0.0161(6) Uani 1 1 d . . . C7 C 1.0306(4) 0.9044(3) 0.4043(2) 0.0226(7) Uani 1 1 d . . . C8 C 0.8674(4) 0.9680(3) 0.3839(2) 0.0239(7) Uani 1 1 d . . . C9 C 0.7147(4) 0.9293(3) 0.4409(2) 0.0243(7) Uani 1 1 d . . . C10 C 0.7260(4) 0.8302(3) 0.5205(2) 0.0200(6) Uani 1 1 d . . . C11 C 0.8892(4) 0.7655(2) 0.5436(2) 0.0152(6) Uani 1 1 d . . . C12 C 0.9069(3) 0.6643(2) 0.63036(19) 0.0120(6) Uani 1 1 d . . . C13 C 0.6064(3) 0.6016(2) 0.7053(2) 0.0158(6) Uani 1 1 d . . . C14 C 0.4443(4) 0.6275(3) 0.7801(2) 0.0178(6) Uani 1 1 d . . . C15 C 0.4035(4) 0.7621(3) 0.7780(2) 0.0202(6) Uani 1 1 d . . . C16 C 0.5584(3) 0.8136(2) 0.7996(2) 0.0158(6) Uani 1 1 d . . . C17 C 0.5332(4) 0.9195(3) 0.8410(2) 0.0216(7) Uani 1 1 d . . . C18 C 0.6727(4) 0.9693(3) 0.8628(2) 0.0212(7) Uani 1 1 d . . . C19 C 0.8429(4) 0.9117(2) 0.8448(2) 0.0160(6) Uani 1 1 d . . . C20 C 0.8725(4) 0.8065(2) 0.8037(2) 0.0159(6) Uani 1 1 d . . . C21 C 0.7324(3) 0.7575(2) 0.78024(19) 0.0132(6) Uani 1 1 d . . . C22 C 1.1580(4) 0.3606(3) 0.8872(2) 0.0165(6) Uani 1 1 d . . . C23 C 1.3391(4) 0.2993(3) 0.9106(2) 0.0223(7) Uani 1 1 d . . . C24 C 1.4136(4) 0.2595(3) 0.7397(2) 0.0233(7) Uani 1 1 d . . . C25 C 1.2360(4) 0.3195(3) 0.7082(2) 0.0192(6) Uani 1 1 d . . . C26 C 0.7923(3) 0.4805(2) 0.8929(2) 0.0156(6) Uani 1 1 d . . . C27 C 0.9692(5) 1.0743(3) 0.8816(3) 0.0320(8) Uani 1 1 d . . . H1 H 1.322(4) 0.530(3) 0.585(2) 0.023(8) Uiso 1 1 d . . . H2 H 1.194(4) 0.539(3) 0.503(2) 0.021(8) Uiso 1 1 d . . . H3 H 1.142(4) 0.934(3) 0.363(2) 0.020(8) Uiso 1 1 d . . . H4 H 0.864(4) 1.032(3) 0.332(2) 0.013(7) Uiso 1 1 d . . . H5 H 0.600(4) 0.977(3) 0.424(2) 0.026(8) Uiso 1 1 d . . . H6 H 0.618(4) 0.808(3) 0.559(2) 0.019(8) Uiso 1 1 d . . . H7 H 0.465(4) 0.591(3) 0.852(3) 0.032(9) Uiso 1 1 d . . . H8 H 0.348(4) 0.594(3) 0.762(2) 0.021(8) Uiso 1 1 d . . . H9 H 0.309(5) 0.781(3) 0.826(3) 0.047(11) Uiso 1 1 d . . . H10 H 0.364(4) 0.801(3) 0.710(3) 0.025(8) Uiso 1 1 d . . . H11 H 0.412(4) 0.953(3) 0.861(2) 0.017(7) Uiso 1 1 d . . . H12 H 0.654(4) 1.040(3) 0.891(2) 0.028(8) Uiso 1 1 d . . . H13 H 0.993(4) 0.766(3) 0.790(2) 0.023(8) Uiso 1 1 d . . . H14 H 1.115(4) 0.425(3) 0.929(2) 0.017(7) Uiso 1 1 d . . . H15 H 1.081(4) 0.303(3) 0.912(2) 0.017(7) Uiso 1 1 d . . . H16 H 1.424(4) 0.360(3) 0.894(2) 0.025(8) Uiso 1 1 d . . . H17 H 1.340(4) 0.261(3) 0.982(2) 0.018(7) Uiso 1 1 d . . . H18 H 1.496(4) 0.321(3) 0.725(2) 0.027(8) Uiso 1 1 d . . . H19 H 1.463(4) 0.198(3) 0.700(2) 0.025(8) Uiso 1 1 d . . . H20 H 1.154(4) 0.262(3) 0.711(2) 0.033(9) Uiso 1 1 d . . . H21 H 1.252(4) 0.358(3) 0.630(3) 0.034(9) Uiso 1 1 d . . . H22 H 0.906(4) 1.133(3) 0.822(3) 0.036(9) Uiso 1 1 d . . . H23 H 0.892(5) 1.089(3) 0.948(3) 0.045(10) Uiso 1 1 d . . . H24 H 1.092(6) 1.094(4) 0.881(3) 0.056(12) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0143(4) 0.0231(4) 0.0191(4) 0.0033(3) 0.0008(3) -0.0045(3) O1 0.0294(12) 0.0184(11) 0.0261(11) -0.0070(9) -0.0020(9) -0.0089(9) O2 0.0299(12) 0.0168(11) 0.0257(12) 0.0008(9) -0.0006(9) 0.0096(9) O3 0.0181(11) 0.0338(13) 0.0265(12) -0.0159(10) 0.0000(8) -0.0056(9) N1 0.0236(14) 0.0316(16) 0.0218(14) 0.0045(12) 0.0015(11) -0.0027(11) N2 0.0168(12) 0.0129(12) 0.0143(12) -0.0022(9) -0.0018(9) 0.0003(9) C1 0.0096(12) 0.0136(14) 0.0121(13) -0.0004(11) -0.0002(10) -0.0020(10) C2 0.0149(13) 0.0105(13) 0.0116(13) -0.0011(11) -0.0012(10) -0.0023(10) C3 0.0155(13) 0.0095(13) 0.0118(13) -0.0015(11) -0.0022(10) -0.0032(10) C4 0.0123(13) 0.0147(14) 0.0137(13) -0.0057(11) -0.0010(10) -0.0054(11) C5 0.0149(14) 0.0164(15) 0.0144(14) -0.0027(12) 0.0005(11) -0.0011(11) C6 0.0181(14) 0.0182(15) 0.0114(13) -0.0028(11) -0.0006(11) -0.0016(11) C7 0.0258(16) 0.0229(17) 0.0165(15) 0.0004(12) 0.0003(12) -0.0029(13) C8 0.0301(17) 0.0211(17) 0.0138(14) 0.0051(13) 0.0014(12) 0.0028(13) C9 0.0267(17) 0.0261(17) 0.0157(15) -0.0005(13) -0.0047(12) 0.0076(14) C10 0.0210(15) 0.0212(16) 0.0151(14) -0.0011(12) -0.0008(12) 0.0015(12) C11 0.0191(14) 0.0154(14) 0.0115(13) -0.0036(11) -0.0015(11) -0.0023(11) C12 0.0141(13) 0.0118(14) 0.0101(13) -0.0009(11) -0.0004(10) -0.0040(10) C13 0.0150(14) 0.0138(14) 0.0166(14) 0.0015(12) -0.0031(11) -0.0002(11) C14 0.0130(14) 0.0237(16) 0.0164(15) -0.0021(12) -0.0004(11) -0.0045(12) C15 0.0123(14) 0.0253(17) 0.0217(16) -0.0040(13) -0.0022(12) 0.0015(12) C16 0.0171(14) 0.0162(15) 0.0114(13) 0.0014(11) -0.0012(11) 0.0008(11) C17 0.0213(16) 0.0186(16) 0.0215(15) -0.0015(13) -0.0009(12) 0.0042(12) C18 0.0288(17) 0.0142(15) 0.0202(15) -0.0054(13) -0.0017(12) 0.0004(13) C19 0.0191(14) 0.0148(14) 0.0127(13) 0.0014(11) 0.0014(11) -0.0054(11) C20 0.0169(15) 0.0154(15) 0.0133(14) 0.0005(11) 0.0024(11) -0.0032(12) C21 0.0174(14) 0.0117(14) 0.0085(13) 0.0020(11) -0.0013(10) -0.0011(11) C22 0.0183(15) 0.0121(14) 0.0169(14) 0.0003(12) -0.0013(11) 0.0003(12) C23 0.0248(17) 0.0194(16) 0.0196(16) 0.0008(13) -0.0031(13) 0.0017(13) C24 0.0256(16) 0.0163(16) 0.0232(16) -0.0034(13) 0.0046(13) 0.0047(13) C25 0.0215(15) 0.0143(15) 0.0199(16) -0.0056(12) 0.0038(12) 0.0010(12) C26 0.0129(13) 0.0148(15) 0.0176(15) -0.0016(12) -0.0024(11) 0.0013(11) C27 0.048(2) 0.0193(17) 0.0323(19) -0.0058(15) -0.0054(17) -0.0124(16) _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 S1 C6 1.764(3) . ? S1 C5 1.816(3) . ? O1 C19 1.376(3) . ? O1 C27 1.432(4) . ? O2 C24 1.431(3) . ? O2 C23 1.431(4) . ? O3 C13 1.207(3) . ? N1 C26 1.148(3) . ? N2 C3 1.369(3) . ? N2 C22 1.469(3) . ? N2 C25 1.474(3) . ? C1 C12 1.520(3) . ? C1 C21 1.534(4) . ? C1 C2 1.537(4) . ? C1 C13 1.552(4) . ? C2 C3 1.369(4) . ? C2 C26 1.421(4) . ? C3 C4 1.475(4) . ? C4 C12 1.353(4) . ? C4 C5 1.502(4) . ? C6 C7 1.393(4) . ? C6 C11 1.409(4) . ? C7 C8 1.385(4) . ? C8 C9 1.389(4) . ? C9 C10 1.383(4) . ? C10 C11 1.398(4) . ? C11 C12 1.458(4) . ? C13 C14 1.503(4) . ? C14 C15 1.519(4) . ? C15 C16 1.498(4) . ? C16 C17 1.397(4) . ? C16 C21 1.406(4) . ? C17 C18 1.383(4) . ? C18 C19 1.384(4) . ? C19 C20 1.387(4) . ? C20 C21 1.391(4) . ? C22 C23 1.505(4) . ? C24 C25 1.507(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 C6 S1 C5 100.17(13) . . ? C19 O1 C27 116.7(2) . . ? C24 O2 C23 109.5(2) . . ? C3 N2 C22 118.8(2) . . ? C3 N2 C25 119.4(2) . . ? C22 N2 C25 112.6(2) . . ? C12 C1 C21 111.8(2) . . ? C12 C1 C2 101.0(2) . . ? C21 C1 C2 113.6(2) . . ? C12 C1 C13 111.8(2) . . ? C21 C1 C13 112.6(2) . . ? C2 C1 C13 105.3(2) . . ? C3 C2 C26 128.0(2) . . ? C3 C2 C1 110.4(2) . . ? C26 C2 C1 121.2(2) . . ? C2 C3 N2 129.0(2) . . ? C2 C3 C4 108.2(2) . . ? N2 C3 C4 122.5(2) . . ? C12 C4 C3 109.7(2) . . ? C12 C4 C5 123.3(2) . . ? C3 C4 C5 126.9(2) . . ? C4 C5 S1 109.32(19) . . ? C7 C6 C11 120.2(3) . . ? C7 C6 S1 117.8(2) . . ? C11 C6 S1 121.8(2) . . ? C8 C7 C6 120.3(3) . . ? C7 C8 C9 119.9(3) . . ? C10 C9 C8 120.1(3) . . ? C9 C10 C11 121.2(3) . . ? C10 C11 C6 118.3(3) . . ? C10 C11 C12 122.7(2) . . ? C6 C11 C12 119.0(2) . . ? C4 C12 C11 124.3(2) . . ? C4 C12 C1 110.7(2) . . ? C11 C12 C1 124.8(2) . . ? O3 C13 C14 123.7(2) . . ? O3 C13 C1 121.3(2) . . ? C14 C13 C1 115.0(2) . . ? C13 C14 C15 109.3(2) . . ? C16 C15 C14 112.0(2) . . ? C17 C16 C21 117.9(3) . . ? C17 C16 C15 120.5(2) . . ? C21 C16 C15 121.7(2) . . ? C18 C17 C16 122.1(3) . . ? C17 C18 C19 119.2(3) . . ? O1 C19 C18 124.0(2) . . ? O1 C19 C20 115.8(2) . . ? C18 C19 C20 120.1(3) . . ? C19 C20 C21 120.7(2) . . ? C20 C21 C16 120.0(2) . . ? C20 C21 C1 118.1(2) . . ? C16 C21 C1 121.8(2) . . ? N2 C22 C23 109.4(2) . . ? O2 C23 C22 111.2(2) . . ? O2 C24 C25 110.9(2) . . ? N2 C25 C24 109.7(2) . . ? N1 C26 C2 178.5(3) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.448 _refine_diff_density_min -0.455 _refine_diff_density_rms 0.100 data_rp-vjr-123b _database_code_depnum_ccdc_archive 'CCDC 841513' #TrackingRef 'web_deposit_cif_file_0_HardeshK.Maurya_1324060279.3. #X-Ray 11d (rp-vjr-123b).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C53 H48 Br2 N4 O4' _chemical_formula_weight 964.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.883(5) _cell_length_b 11.024(5) _cell_length_c 14.736(5) _cell_angle_alpha 110.363(5) _cell_angle_beta 96.456(5) _cell_angle_gamma 104.041(5) _cell_volume 1137.1(10) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2888 _cell_measurement_theta_min 2.992 _cell_measurement_theta_max 29.2455 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 1.833 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.46684 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _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 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9853 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10794 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0634 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 29.31 _reflns_number_total 5276 _reflns_number_gt 3141 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0990P)^2^+0.5861P] 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 5276 _refine_ls_number_parameters 283 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1261 _refine_ls_R_factor_gt 0.0714 _refine_ls_wR_factor_ref 0.2021 _refine_ls_wR_factor_gt 0.1698 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 O1 O 0.1409(4) 0.4025(3) 0.8924(2) 0.0535(8) Uani 1 1 d . . . N1 N 0.7049(4) 0.5364(3) 0.7810(2) 0.0390(7) Uani 1 1 d . . . C10 C 0.2928(5) 0.2831(4) 0.7758(2) 0.0328(8) Uani 1 1 d . . . C7 C 0.5667(5) 0.4496(4) 0.7940(2) 0.0339(8) Uani 1 1 d . . . C23 C 0.2392(5) 0.1373(4) 0.6977(2) 0.0341(8) Uani 1 1 d . . . C9 C 0.4312(5) 0.3059(4) 0.8654(2) 0.0313(8) Uani 1 1 d . . . C19 C 0.1305(5) 0.3254(4) 0.8087(3) 0.0398(9) Uani 1 1 d . . . C26 C 0.3330(6) -0.0540(4) 0.6050(3) 0.0477(10) Uani 1 1 d . . . C22 C 0.0599(5) 0.0600(4) 0.6549(3) 0.0394(9) Uani 1 1 d . . . C8 C 0.5817(5) 0.3996(4) 0.8732(2) 0.0339(8) Uani 1 1 d . . . H8 H 0.6837 0.4294 0.9230 0.041 Uiso 1 1 calc R . . C11 C 0.3928(5) 0.3857(4) 0.7376(2) 0.0319(8) Uani 1 1 d . . . C13 C 0.4002(5) 0.2340(4) 0.9320(2) 0.0328(8) Uani 1 1 d . . . C28 C 0.3735(5) 0.0799(4) 0.6702(3) 0.0420(9) Uani 1 1 d . . . H28 H 0.4927 0.1322 0.6962 0.050 Uiso 1 1 calc R . . C5 C 0.8564(8) 0.6107(6) 0.6640(4) 0.019 Uiso 0.50 1 d P . . H5A H 0.8403 0.6461 0.6130 0.023 Uiso 0.50 1 calc PR . . H5B H 0.8859 0.5269 0.6352 0.023 Uiso 0.50 1 calc PR . . C20 C -0.0372(6) 0.2688(5) 0.7287(3) 0.0535(11) Uani 1 1 d . . . H20A H -0.1335 0.2972 0.7568 0.064 Uiso 1 1 calc R . . H20B H -0.0171 0.3046 0.6780 0.064 Uiso 1 1 calc R . . C2 C 1.0288(5) 0.6570(5) 0.8284(3) 0.0486(10) Uani 1 1 d . . . H2A H 1.0639 0.5752 0.8025 0.058 Uiso 1 1 calc R . . H2B H 1.1231 0.7231 0.8841 0.058 Uiso 1 1 calc R . . C21 C -0.0909(5) 0.1169(5) 0.6827(3) 0.0526(11) Uani 1 1 d . . . H21A H -0.1844 0.0851 0.6237 0.063 Uiso 1 1 calc R . . H21B H -0.1410 0.0815 0.7289 0.063 Uiso 1 1 calc R . . N2 N 0.2275(6) 0.4117(5) 0.5906(3) 0.0699(12) Uani 1 1 d . . . C14 C 0.5179(5) 0.2815(5) 1.0227(3) 0.0420(9) Uani 1 1 d . . . H14 H 0.6138 0.3599 1.0411 0.050 Uiso 1 1 calc R . . C18 C 0.2577(6) 0.1187(4) 0.9079(3) 0.0456(10) Uani 1 1 d . . . H18 H 0.1752 0.0862 0.8481 0.055 Uiso 1 1 calc R . . C25 C 0.1564(6) -0.1305(4) 0.5640(3) 0.0511(11) Uani 1 1 d . . . H25 H 0.1278 -0.2206 0.5203 0.061 Uiso 1 1 calc R . . C24 C 0.0235(6) -0.0731(4) 0.5879(3) 0.0475(10) Uani 1 1 d . . . H24 H -0.0951 -0.1248 0.5584 0.057 Uiso 1 1 calc R . . C3 C 0.8587(5) 0.6252(4) 0.8633(3) 0.0426(9) Uani 1 1 d . . . H3A H 0.8736 0.5812 0.9091 0.051 Uiso 1 1 calc R . . H3B H 0.8343 0.7092 0.8989 0.051 Uiso 1 1 calc R . . C4 C 0.6856(6) 0.5823(5) 0.6996(3) 0.0532(11) Uani 1 1 d . . . H4A H 0.6497 0.6642 0.7216 0.064 Uiso 1 1 calc R . . H4B H 0.5919 0.5133 0.6450 0.064 Uiso 1 1 calc R . . C12 C 0.3075(5) 0.4034(4) 0.6565(3) 0.0419(9) Uani 1 1 d . . . C1 C 1.0083(6) 0.7125(6) 0.7491(4) 0.0660(14) Uani 1 1 d . . . H1A H 1.1187 0.7283 0.7257 0.079 Uiso 1 1 calc R . . H1B H 0.9826 0.7982 0.7758 0.079 Uiso 1 1 calc R . . C17 C 0.2353(7) 0.0512(5) 0.9700(3) 0.0534(11) Uani 1 1 d . . . H17 H 0.1391 -0.0267 0.9522 0.064 Uiso 1 1 calc R . . C15 C 0.4953(6) 0.2145(5) 1.0864(3) 0.0534(12) Uani 1 1 d . . . H15 H 0.5742 0.2474 1.1474 0.064 Uiso 1 1 calc R . . C16 C 0.3540(6) 0.0983(5) 1.0577(3) 0.0485(11) Uani 1 1 d . . . Br1 Br 0.32374(9) 0.00819(7) 1.14565(5) 0.0908(3) Uani 1 1 d . . . O2 O 0.4761(5) -0.1005(4) 0.5860(3) 0.0742(11) Uani 1 1 d . . . C27 C 0.4422(9) -0.2385(6) 0.5236(5) 0.105(3) Uani 1 1 d . . . H27A H 0.5538 -0.2573 0.5166 0.157 Uiso 1 1 calc R . . H27B H 0.3742 -0.2564 0.4596 0.157 Uiso 1 1 calc R . . H27C H 0.3756 -0.2954 0.5523 0.157 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 O1 0.0522(18) 0.061(2) 0.0439(16) 0.0123(15) 0.0130(13) 0.0224(15) N1 0.0327(17) 0.0434(19) 0.0346(15) 0.0174(14) 0.0032(13) -0.0011(15) C10 0.0298(19) 0.031(2) 0.0315(17) 0.0090(15) 0.0028(14) 0.0039(15) C7 0.034(2) 0.036(2) 0.0285(16) 0.0105(15) 0.0065(15) 0.0079(17) C23 0.033(2) 0.033(2) 0.0292(17) 0.0101(15) 0.0028(15) 0.0021(17) C9 0.032(2) 0.032(2) 0.0268(16) 0.0088(14) 0.0044(14) 0.0096(17) C19 0.032(2) 0.038(2) 0.044(2) 0.0159(18) 0.0074(17) 0.0034(17) C26 0.051(3) 0.044(3) 0.040(2) 0.0088(18) 0.0082(19) 0.015(2) C22 0.034(2) 0.043(2) 0.0313(17) 0.0143(16) -0.0020(15) -0.0011(18) C8 0.0291(19) 0.038(2) 0.0302(17) 0.0138(15) 0.0014(14) 0.0037(17) C11 0.0309(19) 0.0306(19) 0.0294(16) 0.0110(14) 0.0023(14) 0.0039(16) C13 0.0307(19) 0.034(2) 0.0337(17) 0.0131(15) 0.0087(15) 0.0099(16) C28 0.032(2) 0.037(2) 0.042(2) 0.0060(17) 0.0021(17) -0.0005(17) C20 0.035(2) 0.063(3) 0.057(3) 0.019(2) 0.009(2) 0.014(2) C2 0.034(2) 0.045(3) 0.065(3) 0.025(2) 0.0096(19) 0.0059(19) C21 0.034(2) 0.062(3) 0.049(2) 0.017(2) 0.0056(19) 0.003(2) N2 0.056(3) 0.091(3) 0.062(2) 0.045(2) -0.005(2) 0.005(2) C14 0.033(2) 0.056(3) 0.044(2) 0.0276(19) 0.0072(17) 0.0120(19) C18 0.051(3) 0.037(2) 0.040(2) 0.0146(17) 0.0077(18) 0.000(2) C25 0.059(3) 0.035(2) 0.038(2) 0.0025(17) -0.003(2) 0.002(2) C24 0.040(2) 0.042(2) 0.042(2) 0.0101(19) -0.0039(18) -0.0044(19) C3 0.032(2) 0.045(2) 0.0389(19) 0.0127(18) 0.0011(16) -0.0012(18) C4 0.048(3) 0.061(3) 0.043(2) 0.028(2) -0.0018(19) -0.002(2) C12 0.037(2) 0.047(2) 0.0360(19) 0.0173(17) 0.0008(17) 0.0037(19) C1 0.046(3) 0.078(4) 0.071(3) 0.045(3) 0.007(2) -0.008(2) C17 0.065(3) 0.040(2) 0.057(3) 0.021(2) 0.024(2) 0.010(2) C15 0.041(2) 0.089(4) 0.048(2) 0.039(2) 0.0132(19) 0.029(3) C16 0.056(3) 0.057(3) 0.057(3) 0.038(2) 0.029(2) 0.028(2) Br1 0.1162(6) 0.1190(6) 0.1091(5) 0.0943(5) 0.0664(4) 0.0680(5) O2 0.060(2) 0.055(2) 0.078(2) -0.0090(18) 0.0096(18) 0.0211(17) C27 0.090(4) 0.069(4) 0.121(5) -0.012(4) 0.015(4) 0.041(4) _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 O1 C19 1.210(5) . ? N1 C7 1.344(5) . ? N1 C4 1.462(5) . ? N1 C3 1.472(5) . ? C10 C9 1.520(5) . ? C10 C11 1.526(5) . ? C10 C19 1.536(5) . ? C10 C23 1.537(5) . ? C7 C11 1.390(5) . ? C7 C8 1.459(5) . ? C23 C28 1.388(5) . ? C23 C22 1.401(5) . ? C9 C8 1.334(5) . ? C9 C13 1.467(5) . ? C19 C20 1.505(6) . ? C26 O2 1.365(5) . ? C26 C25 1.379(6) . ? C26 C28 1.386(6) . ? C22 C24 1.391(6) . ? C22 C21 1.506(6) . ? C8 H8 0.9300 . ? C11 C12 1.401(5) . ? C13 C18 1.381(6) . ? C13 C14 1.386(5) . ? C28 H28 0.9300 . ? C5 C4 1.501(7) . ? C5 C1 1.515(8) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C20 C21 1.498(7) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C2 C3 1.496(6) . ? C2 C1 1.507(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? N2 C12 1.141(5) . ? C14 C15 1.385(6) . ? C14 H14 0.9300 . ? C18 C17 1.367(6) . ? C18 H18 0.9300 . ? C25 C24 1.369(6) . ? C25 H25 0.9300 . ? C24 H24 0.9300 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C17 C16 1.356(6) . ? C17 H17 0.9300 . ? C15 C16 1.372(7) . ? C15 H15 0.9300 . ? C16 Br1 1.891(4) . ? O2 C27 1.416(6) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? 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 C7 N1 C4 121.5(3) . . ? C7 N1 C3 121.1(3) . . ? C4 N1 C3 114.1(3) . . ? C9 C10 C11 101.6(3) . . ? C9 C10 C19 110.3(3) . . ? C11 C10 C19 107.8(3) . . ? C9 C10 C23 112.4(3) . . ? C11 C10 C23 111.6(3) . . ? C19 C10 C23 112.5(3) . . ? N1 C7 C11 130.0(3) . . ? N1 C7 C8 123.0(3) . . ? C11 C7 C8 106.9(3) . . ? C28 C23 C22 119.2(3) . . ? C28 C23 C10 118.6(3) . . ? C22 C23 C10 122.1(3) . . ? C8 C9 C13 126.2(3) . . ? C8 C9 C10 109.8(3) . . ? C13 C9 C10 124.0(3) . . ? O1 C19 C20 123.2(4) . . ? O1 C19 C10 121.6(3) . . ? C20 C19 C10 115.2(3) . . ? O2 C26 C25 124.6(4) . . ? O2 C26 C28 115.9(4) . . ? C25 C26 C28 119.5(4) . . ? C24 C22 C23 118.3(4) . . ? C24 C22 C21 120.3(4) . . ? C23 C22 C21 121.4(4) . . ? C9 C8 C7 111.7(3) . . ? C9 C8 H8 124.1 . . ? C7 C8 H8 124.1 . . ? C7 C11 C12 129.7(3) . . ? C7 C11 C10 109.9(3) . . ? C12 C11 C10 120.4(3) . . ? C18 C13 C14 117.8(4) . . ? C18 C13 C9 122.7(3) . . ? C14 C13 C9 119.5(3) . . ? C26 C28 C23 121.2(4) . . ? C26 C28 H28 119.4 . . ? C23 C28 H28 119.4 . . ? C4 C5 C1 110.5(4) . . ? C4 C5 H5A 109.5 . . ? C1 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? C1 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? C21 C20 C19 111.1(4) . . ? C21 C20 H20A 109.4 . . ? C19 C20 H20A 109.4 . . ? C21 C20 H20B 109.4 . . ? C19 C20 H20B 109.4 . . ? H20A C20 H20B 108.0 . . ? C3 C2 C1 111.7(4) . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? C20 C21 C22 114.3(3) . . ? C20 C21 H21A 108.7 . . ? C22 C21 H21A 108.7 . . ? C20 C21 H21B 108.7 . . ? C22 C21 H21B 108.7 . . ? H21A C21 H21B 107.6 . . ? C15 C14 C13 121.2(4) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C17 C18 C13 121.4(4) . . ? C17 C18 H18 119.3 . . ? C13 C18 H18 119.3 . . ? C24 C25 C26 119.6(4) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? C25 C24 C22 122.1(4) . . ? C25 C24 H24 118.9 . . ? C22 C24 H24 118.9 . . ? N1 C3 C2 112.3(3) . . ? N1 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? N1 C3 H3B 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.9 . . ? N1 C4 C5 112.1(4) . . ? N1 C4 H4A 109.2 . . ? C5 C4 H4A 109.2 . . ? N1 C4 H4B 109.2 . . ? C5 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? N2 C12 C11 175.3(4) . . ? C2 C1 C5 108.8(4) . . ? C2 C1 H1A 109.9 . . ? C5 C1 H1A 109.9 . . ? C2 C1 H1B 109.9 . . ? C5 C1 H1B 109.9 . . ? H1A C1 H1B 108.3 . . ? C16 C17 C18 119.8(4) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C16 C15 C14 118.6(4) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C17 C16 C15 121.2(4) . . ? C17 C16 Br1 120.5(4) . . ? C15 C16 Br1 118.2(3) . . ? C26 O2 C27 118.2(4) . . ? O2 C27 H27A 109.5 . . ? O2 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O2 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? 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 C4 N1 C7 C11 2.3(6) . . . . ? C3 N1 C7 C11 160.6(4) . . . . ? C4 N1 C7 C8 178.9(4) . . . . ? C3 N1 C7 C8 -22.9(5) . . . . ? C9 C10 C23 C28 -46.9(4) . . . . ? C11 C10 C23 C28 66.5(4) . . . . ? C19 C10 C23 C28 -172.2(3) . . . . ? C9 C10 C23 C22 131.9(4) . . . . ? C11 C10 C23 C22 -114.8(4) . . . . ? C19 C10 C23 C22 6.6(5) . . . . ? C11 C10 C9 C8 -2.0(4) . . . . ? C19 C10 C9 C8 -116.1(3) . . . . ? C23 C10 C9 C8 117.5(3) . . . . ? C11 C10 C9 C13 178.1(3) . . . . ? C19 C10 C9 C13 64.0(4) . . . . ? C23 C10 C9 C13 -62.4(4) . . . . ? C9 C10 C19 O1 20.8(5) . . . . ? C11 C10 C19 O1 -89.3(4) . . . . ? C23 C10 C19 O1 147.2(4) . . . . ? C9 C10 C19 C20 -161.7(4) . . . . ? C11 C10 C19 C20 88.3(4) . . . . ? C23 C10 C19 C20 -35.3(5) . . . . ? C28 C23 C22 C24 1.5(5) . . . . ? C10 C23 C22 C24 -177.3(4) . . . . ? C28 C23 C22 C21 179.4(4) . . . . ? C10 C23 C22 C21 0.6(6) . . . . ? C13 C9 C8 C7 179.6(3) . . . . ? C10 C9 C8 C7 -0.3(4) . . . . ? N1 C7 C8 C9 -174.5(3) . . . . ? C11 C7 C8 C9 2.7(4) . . . . ? N1 C7 C11 C12 -6.7(7) . . . . ? C8 C7 C11 C12 176.3(4) . . . . ? N1 C7 C11 C10 173.0(4) . . . . ? C8 C7 C11 C10 -3.9(4) . . . . ? C9 C10 C11 C7 3.7(4) . . . . ? C19 C10 C11 C7 119.6(3) . . . . ? C23 C10 C11 C7 -116.3(3) . . . . ? C9 C10 C11 C12 -176.6(3) . . . . ? C19 C10 C11 C12 -60.6(4) . . . . ? C23 C10 C11 C12 63.4(4) . . . . ? C8 C9 C13 C18 -165.4(4) . . . . ? C10 C9 C13 C18 14.5(5) . . . . ? C8 C9 C13 C14 14.0(5) . . . . ? C10 C9 C13 C14 -166.1(3) . . . . ? O2 C26 C28 C23 -177.9(4) . . . . ? C25 C26 C28 C23 2.1(6) . . . . ? C22 C23 C28 C26 -3.0(6) . . . . ? C10 C23 C28 C26 175.8(4) . . . . ? O1 C19 C20 C21 -126.1(4) . . . . ? C10 C19 C20 C21 56.5(5) . . . . ? C19 C20 C21 C22 -47.5(5) . . . . ? C24 C22 C21 C20 -161.9(4) . . . . ? C23 C22 C21 C20 20.3(6) . . . . ? C18 C13 C14 C15 1.0(6) . . . . ? C9 C13 C14 C15 -178.4(4) . . . . ? C14 C13 C18 C17 -1.6(6) . . . . ? C9 C13 C18 C17 177.8(4) . . . . ? O2 C26 C25 C24 -179.7(4) . . . . ? C28 C26 C25 C24 0.3(7) . . . . ? C26 C25 C24 C22 -1.8(7) . . . . ? C23 C22 C24 C25 0.9(6) . . . . ? C21 C22 C24 C25 -177.1(4) . . . . ? C7 N1 C3 C2 150.3(4) . . . . ? C4 N1 C3 C2 -50.0(5) . . . . ? C1 C2 C3 N1 53.0(5) . . . . ? C7 N1 C4 C5 -148.7(4) . . . . ? C3 N1 C4 C5 51.6(5) . . . . ? C1 C5 C4 N1 -55.7(6) . . . . ? C7 C11 C12 N2 -175(5) . . . . ? C10 C11 C12 N2 5(6) . . . . ? C3 C2 C1 C5 -57.0(6) . . . . ? C4 C5 C1 C2 58.0(6) . . . . ? C13 C18 C17 C16 0.5(7) . . . . ? C13 C14 C15 C16 0.6(6) . . . . ? C18 C17 C16 C15 1.2(6) . . . . ? C18 C17 C16 Br1 179.1(3) . . . . ? C14 C15 C16 C17 -1.7(6) . . . . ? C14 C15 C16 Br1 -179.6(3) . . . . ? C25 C26 O2 C27 -3.1(8) . . . . ? C28 C26 O2 C27 176.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.847 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 1.250 _refine_diff_density_min -0.422 _refine_diff_density_rms 0.077