# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/479 data_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H25 N O3 Si' _chemical_formula_weight 283.44 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' 'Si' 'Si' 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.150(9) _cell_length_b 9.834(11) _cell_length_c 12.116(13) _cell_angle_alpha 90.00 _cell_angle_beta 94.660(10) _cell_angle_gamma 90.00 _cell_volume 849.1(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.109 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.142 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Marresearch Image Plate' _diffrn_measurement_method '95 frames at 2^o intervals, counting time 2 min.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2961 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 25.87 _reflns_number_total 2837 _reflns_number_gt 2127 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XDS (Kabsch, 1991)' _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'PLATON(Spek,1994)' _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 w=1/[\s^2^(Fo^2^)+(0.0743P)^2^+0.3267P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.027(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(3) _refine_ls_number_reflns 2837 _refine_ls_number_parameters 179 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0964 _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.1650 _refine_ls_wR_factor_gt 0.1513 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Si10 Si 0.53447(15) 0.25942(14) 0.21995(9) 0.0604(3) Uani 1 d . . . O1 O 0.4327(4) 0.2667(4) 0.3375(2) 0.0724(8) Uani 1 d . . . C2 C 0.3624(6) 0.1570(5) 0.3987(3) 0.0624(11) Uani 1 d . . . H2 H 0.3598 0.0713 0.3574 0.075 Uiso 1 calc R . . C9 C 0.4761(6) 0.1461(5) 0.5101(4) 0.0655(11) Uani 1 d . . . H9A H 0.4579 0.0582 0.5439 0.079 Uiso 1 calc R . . H9B H 0.6088 0.1591 0.5021 0.079 Uiso 1 calc R . . C8 C 0.3995(5) 0.2591(6) 0.5782(3) 0.0631(10) Uani 1 d . . . C7 C 0.1963(5) 0.2860(4) 0.5330(3) 0.0536(10) Uani 1 d . . . H7 H 0.1700 0.3827 0.5195 0.064 Uiso 1 calc R . . C6 C 0.0628(5) 0.2209(5) 0.6061(3) 0.0606(11) Uani 1 d . . . N5 N -0.0053(5) 0.1093(5) 0.5681(3) 0.0769(11) Uani 1 d . . . O4 O 0.0651(5) 0.0822(4) 0.4632(3) 0.0866(11) Uani 1 d . . . C3 C 0.1669(6) 0.1998(5) 0.4289(3) 0.0651(11) Uani 1 d . . . H3 H 0.0974 0.2490 0.3683 0.078 Uiso 1 calc R . . C101 C 0.3533(6) 0.2425(6) 0.0991(4) 0.0757(13) Uani 1 d . . . C102 C 0.7008(7) 0.1142(7) 0.2226(5) 0.0854(16) Uani 1 d . . . H12A H 0.6317 0.0304 0.2186 0.102 Uiso 1 calc R . . H12B H 0.7811 0.1166 0.2900 0.102 Uiso 1 calc R . . H12C H 0.7755 0.1205 0.1604 0.102 Uiso 1 calc R . . C103 C 0.6612(9) 0.4226(7) 0.2152(5) 0.097(2) Uani 1 d . . . H13A H 0.7567 0.4267 0.2756 0.117 Uiso 1 calc R . . H13B H 0.5747 0.4964 0.2212 0.117 Uiso 1 calc R . . H13C H 0.7182 0.4296 0.1464 0.117 Uiso 1 calc R . . C104 C 0.4536(9) 0.2418(9) -0.0089(4) 0.109(2) Uani 1 d . . . H14A H 0.3630 0.2538 -0.0710 0.131 Uiso 1 calc R . . H14B H 0.5172 0.1566 -0.0157 0.131 Uiso 1 calc R . . H14C H 0.5432 0.3147 -0.0071 0.131 Uiso 1 calc R . . C105 C 0.2428(9) 0.1089(7) 0.1072(5) 0.098(2) Uani 1 d . . . H15A H 0.1616 0.0965 0.0409 0.117 Uiso 1 calc R . . H15B H 0.1691 0.1129 0.1699 0.117 Uiso 1 calc R . . H15C H 0.3290 0.0340 0.1159 0.117 Uiso 1 calc R . . C106 C 0.2150(11) 0.3596(8) 0.0963(6) 0.119(3) Uani 1 d . . . H16A H 0.1525 0.3602 0.1635 0.143 Uiso 1 calc R . . H16B H 0.1240 0.3490 0.0342 0.143 Uiso 1 calc R . . H16C H 0.2810 0.4438 0.0895 0.143 Uiso 1 calc R . . O81 O 0.4790(5) 0.3170(4) 0.6552(3) 0.0988(13) Uani 1 d . . . C61 C 0.0130(8) 0.2838(8) 0.7138(4) 0.0898(18) Uani 1 d . . . H61A H 0.1283 0.3080 0.7572 0.108 Uiso 1 calc R . . H61B H -0.0562 0.3672 0.6972 0.108 Uiso 1 calc R . . C62 C -0.0996(8) 0.1959(7) 0.7820(5) 0.0987(19) Uani 1 d . . . H62A H -0.0423 0.1077 0.7894 0.118 Uiso 1 calc R . . H62B H -0.2242 0.1870 0.7468 0.118 Uiso 1 calc R . . H62C H -0.1053 0.2358 0.8539 0.118 Uiso 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 Si10 0.0640(6) 0.0637(7) 0.0547(6) 0.0017(6) 0.0124(4) -0.0046(7) O1 0.0912(19) 0.0651(18) 0.0647(17) -0.0017(19) 0.0291(14) 0.007(2) C2 0.072(3) 0.058(2) 0.058(2) 0.003(2) 0.014(2) -0.001(2) C9 0.061(2) 0.076(3) 0.061(3) 0.007(2) 0.0131(19) 0.016(2) C8 0.059(2) 0.070(2) 0.061(2) 0.006(3) 0.0085(17) -0.015(3) C7 0.053(2) 0.049(2) 0.060(2) 0.0034(18) 0.0041(16) 0.0042(18) C6 0.0499(19) 0.067(3) 0.066(2) 0.000(2) 0.0105(18) -0.005(2) N5 0.065(2) 0.086(3) 0.082(3) -0.004(2) 0.016(2) -0.015(2) O4 0.088(2) 0.095(3) 0.079(2) -0.0240(19) 0.0163(18) -0.034(2) C3 0.063(2) 0.078(3) 0.054(2) 0.007(2) -0.0014(18) -0.005(2) C101 0.078(3) 0.082(4) 0.066(3) -0.011(3) 0.001(2) 0.010(3) C102 0.064(3) 0.102(4) 0.092(4) 0.002(3) 0.013(3) 0.014(3) C103 0.105(5) 0.105(5) 0.083(4) -0.006(3) 0.018(3) -0.024(4) C104 0.143(5) 0.131(6) 0.053(3) 0.003(4) 0.012(3) -0.009(5) C105 0.090(4) 0.113(5) 0.089(4) -0.029(4) -0.005(3) -0.023(4) C106 0.120(5) 0.120(6) 0.111(5) -0.004(4) -0.025(4) 0.036(5) O81 0.082(2) 0.116(3) 0.096(3) -0.040(2) -0.012(2) -0.011(2) C61 0.094(3) 0.102(5) 0.078(3) -0.004(3) 0.029(3) -0.009(3) C62 0.090(3) 0.122(5) 0.086(4) 0.025(3) 0.021(3) -0.005(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 Si10 O1 1.653(3) . ? Si10 C103 1.846(7) . ? Si10 C102 1.857(6) . ? Si10 C101 1.882(5) . ? O1 C2 1.423(6) . ? C2 C9 1.522(6) . ? C2 C3 1.533(6) . ? C9 C8 1.513(7) . ? C8 O81 1.196(5) . ? C8 C7 1.534(6) . ? C7 C6 1.498(6) . ? C7 C3 1.520(6) . ? C6 N5 1.272(6) . ? C6 C61 1.512(7) . ? N5 O4 1.429(5) . ? O4 C3 1.445(6) . ? C101 C106 1.517(9) . ? C101 C104 1.542(7) . ? C101 C105 1.540(8) . ? C61 C62 1.478(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Si10 C103 103.9(2) . . ? O1 Si10 C102 110.2(2) . . ? C103 Si10 C102 110.7(3) . . ? O1 Si10 C101 110.5(2) . . ? C103 Si10 C101 111.2(3) . . ? C102 Si10 C101 110.1(3) . . ? C2 O1 Si10 128.0(3) . . ? O1 C2 C9 109.3(4) . . ? O1 C2 C3 106.5(3) . . ? C9 C2 C3 103.8(3) . . ? C8 C9 C2 104.0(4) . . ? O81 C8 C9 127.2(4) . . ? O81 C8 C7 124.9(5) . . ? C9 C8 C7 107.8(4) . . ? C6 C7 C3 101.6(3) . . ? C6 C7 C8 110.2(3) . . ? C3 C7 C8 105.3(3) . . ? N5 C6 C7 113.4(4) . . ? N5 C6 C61 123.8(4) . . ? C7 C6 C61 122.8(4) . . ? C6 N5 O4 109.4(4) . . ? N5 O4 C3 109.2(3) . . ? O4 C3 C7 104.3(3) . . ? O4 C3 C2 109.8(4) . . ? C7 C3 C2 106.5(3) . . ? C106 C101 C104 109.4(5) . . ? C106 C101 C105 108.2(5) . . ? C104 C101 C105 109.1(5) . . ? C106 C101 Si10 110.9(4) . . ? C104 C101 Si10 108.8(3) . . ? C105 C101 Si10 110.5(4) . . ? C62 C61 C6 114.8(6) . . ? _refine_diff_density_max 0.164 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.036 _publ_section_references ; Kabsch, W. (1988), J.Appl.Cryst 21 916-932. Sheldrick, G.M. (1990) SHELX86, Acta Cryst. A46 467-480. Sheldrick, G.M. (1993) SHELXL program for crystallography refinement. University of Gottingen, Germany. Spek, A.L., (1994) PLATON-94 program, Utrecht University, The Netherlands ; #===END data_7b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H24 Br N O3 Si' _chemical_formula_weight 410.38 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' 'Si' 'Si' 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.091(9) _cell_length_b 25.43(3) _cell_length_c 11.529(14) _cell_angle_alpha 90.00 _cell_angle_beta 96.490(10) _cell_angle_gamma 90.00 _cell_volume 2065(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 2.062 _exptl_absorpt_correction_type 'DIFABS (Walker and Stuart, 1983)' _exptl_absorpt_correction_T_min 0.168 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Marresearch Image Plate' _diffrn_measurement_method '95 frames at 2^o intervals, counting time 2 min.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2619 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1236 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 25.96 _reflns_number_total 2619 _reflns_number_gt 969 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XDS (Kabsch, 1991)' _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'PLATON(Spek,1994)' _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 w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.000(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2619 _refine_ls_number_parameters 204 _refine_ls_number_restraints 31 _refine_ls_R_factor_all 0.2598 _refine_ls_R_factor_gt 0.1249 _refine_ls_wR_factor_ref 0.3912 _refine_ls_wR_factor_gt 0.3276 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.130 _refine_ls_shift/su_max 1.907 _refine_ls_shift/su_mean 0.100 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C6 C 0.321(3) 0.0167(6) 0.2412(13) 0.089(5) Uani 1 d . . . N5 N 0.153(2) -0.0048(5) 0.2205(12) 0.102(4) Uani 1 d . . . O4 O 0.0273(14) 0.0287(6) 0.1533(12) 0.122(4) Uani 1 d . . . C3 C 0.114(2) 0.0780(7) 0.1355(15) 0.092(5) Uani 1 d . . . H3 H 0.0552 0.1066 0.1758 0.111 Uiso 1 calc R . . C2 C 0.112(2) 0.0886(7) 0.0097(17) 0.100(5) Uani 1 d . . . H2 H -0.0043 0.0758 -0.0354 0.120 Uiso 1 calc R . . C9 C 0.288(3) 0.0628(7) -0.0284(19) 0.118(6) Uani 1 d . . . H9A H 0.2641 0.0261 -0.0478 0.141 Uiso 1 calc R . . H9B H 0.3285 0.0806 -0.0956 0.141 Uiso 1 calc R . . C8 C 0.428(3) 0.0680(7) 0.073(2) 0.117(7) Uani 1 d . . . C7 C 0.330(2) 0.0689(6) 0.1861(13) 0.089(5) Uani 1 d . . . H7 H 0.3793 0.0963 0.2410 0.107 Uiso 1 calc R . . O81 O 0.602(2) 0.0722(5) 0.0755(13) 0.145(5) Uani 1 d . . . O1 O 0.1357(15) 0.1452(5) -0.0036(9) 0.114(4) Uani 1 d D . . Si10 Si 0.0041(10) 0.1833(3) -0.0920(7) 0.160(3) Uani 1 d D . . C101 C -0.243(3) 0.1715(14) -0.120(4) 0.36(3) Uiso 1 d D . . H11A H -0.2705 0.1539 -0.1935 0.433 Uiso 1 calc R . . H11B H -0.3104 0.2044 -0.1221 0.433 Uiso 1 calc R . . H11C H -0.2836 0.1499 -0.0590 0.433 Uiso 1 calc R . . C102 C 0.079(6) 0.1621(15) -0.242(2) 0.36(2) Uiso 1 d D . . H12A H 0.1074 0.1928 -0.2852 0.429 Uiso 1 calc R . . H12B H -0.0236 0.1431 -0.2848 0.429 Uiso 1 calc R . . H12C H 0.1887 0.1400 -0.2299 0.429 Uiso 1 calc R . . C103 C 0.100(3) 0.2504(6) -0.085(2) 0.187(10) Uiso 0.48(2) d PD A 1 C104 C -0.003(8) 0.2744(18) 0.023(4) 0.203(10) Uiso 0.48(2) d PD A 1 H14A H 0.0596 0.2616 0.0956 0.243 Uiso 0.48(2) calc PR A 1 H14B H -0.1339 0.2637 0.0153 0.243 Uiso 0.48(2) calc PR A 1 H14C H 0.0037 0.3121 0.0217 0.243 Uiso 0.48(2) calc PR A 1 C105 C 0.309(4) 0.257(2) -0.034(5) 0.203(10) Uiso 0.48(2) d PD A 1 H15A H 0.3892 0.2422 -0.0871 0.243 Uiso 0.48(2) calc PR A 1 H15B H 0.3300 0.2390 0.0396 0.243 Uiso 0.48(2) calc PR A 1 H15C H 0.3371 0.2936 -0.0228 0.243 Uiso 0.48(2) calc PR A 1 C106 C 0.046(7) 0.2889(18) -0.186(4) 0.203(10) Uiso 0.48(2) d PD A 1 H16A H 0.0765 0.3241 -0.1609 0.243 Uiso 0.48(2) calc PR A 1 H16B H -0.0882 0.2865 -0.2104 0.243 Uiso 0.48(2) calc PR A 1 H16C H 0.1146 0.2801 -0.2504 0.243 Uiso 0.48(2) calc PR A 1 C103 C 0.100(3) 0.2504(6) -0.085(2) 0.187(10) Uiso 0.52(2) d PD A 2 C107 C 0.296(5) 0.2488(18) -0.137(5) 0.203(10) Uiso 0.52(2) d PD A 2 H17A H 0.3198 0.2823 -0.1700 0.243 Uiso 0.52(2) calc PR A 2 H17B H 0.2917 0.2221 -0.1959 0.243 Uiso 0.52(2) calc PR A 2 H17C H 0.3952 0.2408 -0.0756 0.243 Uiso 0.52(2) calc PR A 2 C108 C -0.031(6) 0.2886(16) -0.161(4) 0.203(10) Uiso 0.52(2) d PD A 2 H18A H 0.0133 0.3240 -0.1475 0.243 Uiso 0.52(2) calc PR A 2 H18B H -0.1584 0.2858 -0.1398 0.243 Uiso 0.52(2) calc PR A 2 H18C H -0.0306 0.2797 -0.2414 0.243 Uiso 0.52(2) calc PR A 2 C109 C 0.193(8) 0.2734(18) 0.029(3) 0.203(10) Uiso 0.52(2) d PD A 2 H19A H 0.2730 0.3022 0.0119 0.243 Uiso 0.52(2) calc PR A 2 H19B H 0.2676 0.2468 0.0713 0.243 Uiso 0.52(2) calc PR A 2 H19C H 0.0968 0.2857 0.0743 0.243 Uiso 0.52(2) calc PR A 2 C61 C 0.469(2) -0.0122(6) 0.3127(14) 0.086(4) Uani 1 d . . . C62 C 0.417(2) -0.0554(7) 0.3724(17) 0.107(5) Uani 1 d . . . H62 H 0.2915 -0.0671 0.3654 0.128 Uiso 1 calc R . . C63 C 0.563(3) -0.0820(8) 0.4463(16) 0.110(5) Uani 1 d . . . H63 H 0.5328 -0.1084 0.4968 0.132 Uiso 1 calc R . . C64 C 0.750(2) -0.0677(8) 0.4414(15) 0.106(6) Uani 1 d . . . C65 C 0.657(2) 0.0020(7) 0.3205(14) 0.094(5) Uani 1 d . . . H65 H 0.6905 0.0313 0.2789 0.112 Uiso 1 calc R . . C66 C 0.795(2) -0.0244(6) 0.3854(15) 0.090(5) Uani 1 d . . . H66 H 0.9204 -0.0127 0.3911 0.108 Uiso 1 calc R . . Br64 Br 0.9397(3) -0.10614(9) 0.54085(19) 0.1365(14) Uani 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 C6 0.110(13) 0.086(13) 0.081(11) -0.004(9) 0.055(10) -0.020(10) N5 0.085(9) 0.095(10) 0.133(12) 0.027(9) 0.043(9) 0.002(8) O4 0.075(7) 0.130(11) 0.164(11) 0.020(9) 0.018(8) -0.005(7) C3 0.097(12) 0.094(13) 0.095(14) 0.004(9) 0.050(10) 0.032(9) C2 0.092(11) 0.080(13) 0.128(17) 0.002(10) 0.005(10) 0.024(8) C9 0.157(18) 0.072(12) 0.134(17) 0.024(10) 0.060(15) 0.012(11) C8 0.085(13) 0.089(13) 0.18(2) 0.052(12) 0.007(15) 0.031(10) C7 0.116(12) 0.068(11) 0.093(12) 0.008(8) 0.058(10) -0.001(8) O81 0.115(10) 0.140(11) 0.190(14) 0.074(10) 0.058(10) 0.016(8) O1 0.112(8) 0.111(10) 0.113(9) 0.006(7) -0.013(6) 0.018(7) Si10 0.156(6) 0.117(5) 0.192(7) 0.027(5) -0.044(5) -0.003(4) C61 0.083(11) 0.072(11) 0.107(12) 0.017(9) 0.028(10) 0.014(9) C62 0.079(11) 0.089(13) 0.156(16) 0.010(12) 0.033(12) -0.019(9) C63 0.101(14) 0.119(14) 0.112(15) -0.003(11) 0.021(12) 0.008(11) C64 0.092(12) 0.118(16) 0.115(14) 0.029(11) 0.041(11) 0.036(9) C65 0.060(10) 0.120(14) 0.103(12) 0.002(10) 0.017(9) -0.008(9) C66 0.085(11) 0.083(12) 0.103(12) 0.012(10) 0.009(10) 0.006(9) Br64 0.1337(19) 0.141(2) 0.135(2) 0.0251(13) 0.0162(13) 0.0272(13) _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 C6 N5 1.305(18) . ? C6 C61 1.46(2) . ? C6 C7 1.476(19) . ? N5 O4 1.402(16) . ? O4 C3 1.418(19) . ? C3 C2 1.47(2) . ? C3 C7 1.59(2) . ? C2 O1 1.459(19) . ? C2 C9 1.52(2) . ? C9 C8 1.45(2) . ? C8 O81 1.235(19) . ? C8 C7 1.55(2) . ? O1 Si10 1.623(12) . ? Si10 C101 1.775(17) . ? Si10 C103 1.834(12) . ? Si10 C103 1.834(12) . ? Si10 C102 1.939(18) . ? C103 C106 1.541(19) . ? C103 C105 1.539(19) . ? C103 C104 1.627(19) . ? C103 C109 1.511(19) . ? C103 C108 1.545(19) . ? C103 C107 1.577(19) . ? C61 C65 1.376(19) . ? C61 C62 1.37(2) . ? C62 C63 1.44(2) . ? C63 C64 1.38(2) . ? C64 C66 1.33(2) . ? C64 Br64 1.929(16) . ? C65 C66 1.343(19) . ? 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 N5 C6 C61 118.4(14) . . ? N5 C6 C7 112.4(16) . . ? C61 C6 C7 129.1(15) . . ? C6 N5 O4 110.8(13) . . ? N5 O4 C3 111.1(11) . . ? O4 C3 C2 110.4(15) . . ? O4 C3 C7 103.4(12) . . ? C2 C3 C7 106.7(11) . . ? O1 C2 C3 107.2(14) . . ? O1 C2 C9 106.8(13) . . ? C3 C2 C9 106.9(14) . . ? C8 C9 C2 103.9(16) . . ? O81 C8 C9 129(2) . . ? O81 C8 C7 121(2) . . ? C9 C8 C7 110.2(15) . . ? C6 C7 C8 113.3(12) . . ? C6 C7 C3 101.5(13) . . ? C8 C7 C3 101.4(13) . . ? C2 O1 Si10 126.2(10) . . ? O1 Si10 C101 120.0(14) . . ? O1 Si10 C103 110.1(8) . . ? C101 Si10 C103 121.2(13) . . ? O1 Si10 C103 110.1(8) . . ? C101 Si10 C103 121.2(13) . . ? C103 Si10 C103 0.0(19) . . ? O1 Si10 C102 101.4(13) . . ? C101 Si10 C102 98.9(16) . . ? C103 Si10 C102 99.4(12) . . ? C103 Si10 C102 99.4(12) . . ? C106 C103 C105 111(2) . . ? C106 C103 C104 104(2) . . ? C105 C103 C104 100(2) . . ? C106 C103 Si10 120(2) . . ? C105 C103 Si10 117(2) . . ? C104 C103 Si10 100.9(19) . . ? C109 C103 C108 115(2) . . ? C109 C103 C107 91(3) . . ? C108 C103 C107 108(2) . . ? C109 C103 Si10 122(2) . . ? C108 C103 Si10 111(2) . . ? C107 C103 Si10 107.1(19) . . ? C65 C61 C62 119.5(15) . . ? C65 C61 C6 122.5(15) . . ? C62 C61 C6 117.9(15) . . ? C61 C62 C63 117.2(14) . . ? C64 C63 C62 119.1(17) . . ? C66 C64 C63 121.3(16) . . ? C66 C64 Br64 121.2(15) . . ? C63 C64 Br64 116.7(15) . . ? C66 C65 C61 123.1(16) . . ? C64 C66 C65 118.9(16) . . ? _refine_diff_density_max 0.958 _refine_diff_density_min -0.532 _refine_diff_density_rms 0.114 _publ_section_references ; Kabsch, W. (1988), J.Appl.Cryst 21 916-932. Sheldrick, G.M. (1990) SHELX86, Acta Cryst. A46 467-480. Sheldrick, G.M. (1993) SHELXL program for crystallography refinement. University of Gottingen, Germany. Spek, A.L., (1994) PLATON-94 program, Utrecht University, The Netherlands Walker, N. and Stuart, D., Acta Crystl 1983 A39 158. ; #===END data_12 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H26 Br2 N4 O6' _chemical_formula_weight 698.37 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 monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.513(8) _cell_length_b 49.82(6) _cell_length_c 10.840(14) _cell_angle_alpha 90.00 _cell_angle_beta 103.710(10) _cell_angle_gamma 90.00 _cell_volume 2892(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.604 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 2.854 _exptl_absorpt_correction_type 'DIFABS(Walker and Stuart, 1983)' _exptl_absorpt_correction_T_min 0.242 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Marresearch Image Plate' _diffrn_measurement_method '95 frames at 2^o intervals, counting time 2 min.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8977 _diffrn_reflns_av_R_equivalents 0.0684 _diffrn_reflns_av_sigmaI/netI 0.1013 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -61 _diffrn_reflns_limit_k_max 61 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 26.07 _reflns_number_total 5394 _reflns_number_gt 2935 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XDS (Kabsch, 1991)' _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'PLATON(Spek,1994)' _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 w=1/[\s^2^(Fo^2^)+(0.0886P)^2^+15.4553P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0028(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5394 _refine_ls_number_parameters 382 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2013 _refine_ls_R_factor_gt 0.1080 _refine_ls_wR_factor_ref 0.2893 _refine_ls_wR_factor_gt 0.2553 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.061 _refine_ls_shift/su_mean 0.014 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2A C 0.4386(17) 0.1064(2) 0.2073(9) 0.057(2) Uani 1 d . . . H2A H 0.3495 0.0984 0.1268 0.068 Uiso 1 calc R . . O1A O 0.7059(11) 0.09842(16) 0.2416(6) 0.068(2) Uani 1 d . . . N11A N 0.7395(15) 0.07898(18) 0.3381(8) 0.067(2) Uani 1 d . . . C10A C 0.5435(15) 0.07703(18) 0.3817(8) 0.045(2) Uani 1 d . . . C9A C 0.3394(16) 0.09627(19) 0.3185(8) 0.051(2) Uani 1 d . . . H9A H 0.1773 0.0873 0.2905 0.061 Uiso 1 calc R . . C8A C 0.3248(18) 0.12143(19) 0.4004(10) 0.057(3) Uani 1 d . . . O81A O 0.2579(16) 0.12159(15) 0.4979(7) 0.080(2) Uani 1 d . . . C7A C 0.3978(16) 0.14614(18) 0.3330(7) 0.047(2) Uani 1 d . . . H7A H 0.5511 0.1546 0.3819 0.056 Uiso 1 calc R . . N5A N 0.0739(16) 0.16431(17) 0.1788(7) 0.064(2) Uani 1 d . . . O4A O 0.1949(13) 0.14470(16) 0.1174(6) 0.077(2) Uani 1 d . . . C3A C 0.4238(16) 0.1364(2) 0.2037(8) 0.055(3) Uani 1 d . . . H3A H 0.5700 0.1443 0.1810 0.066 Uiso 1 calc R . . C6A C 0.1879(17) 0.16571(19) 0.2960(9) 0.054(2) Uani 1 d . . . C61A C 0.118(2) 0.1843(2) 0.3890(11) 0.074(3) Uani 1 d . . . H61A H 0.2627 0.1950 0.4284 0.089 Uiso 1 calc R . . H61B H 0.0720 0.1738 0.4553 0.089 Uiso 1 calc R . . C62A C -0.100(3) 0.2034(3) 0.3314(13) 0.101(4) Uani 1 d . . . H62A H -0.2432 0.1931 0.2904 0.121 Uiso 1 calc R . . H62B H -0.0514 0.2150 0.2702 0.121 Uiso 1 calc R . . H62C H -0.1393 0.2141 0.3975 0.121 Uiso 1 calc R . . C13 C 0.710(2) 0.0189(2) 0.6109(12) 0.080(3) Uani 1 d . . . H13 H 0.8300 0.0055 0.6314 0.096 Uiso 1 calc R . . C12A C 0.713(2) 0.0369(2) 0.5134(11) 0.068(3) Uani 1 d . . . H12A H 0.8326 0.0352 0.4660 0.082 Uiso 1 calc R . . C11A C 0.5359(15) 0.05764(19) 0.4861(9) 0.052(2) Uani 1 d . . . C16A C 0.3521(17) 0.0592(2) 0.5499(10) 0.059(3) Uani 1 d . . . H16A H 0.2287 0.0722 0.5278 0.071 Uiso 1 calc R . . C15A C 0.3475(19) 0.04143(19) 0.6481(9) 0.059(3) Uani 1 d . . . H15A H 0.2254 0.0430 0.6940 0.071 Uiso 1 calc R . . C14A C 0.526(2) 0.0214(2) 0.6770(10) 0.065(3) Uani 1 d . . . BR14A Br 0.5087(3) -0.00338(3) 0.80771(14) 0.1077(6) Uani 1 d . . . C14B C 0.788(2) -0.22560(19) 0.0597(11) 0.065(3) Uani 1 d . . . C13B C 0.841(2) -0.2234(2) 0.1892(11) 0.068(3) Uani 1 d . . . H13B H 0.9738 -0.2329 0.2390 0.082 Uiso 1 calc R . . C12B C 0.695(2) -0.2070(2) 0.2458(10) 0.065(3) Uani 1 d . . . H12B H 0.7311 -0.2058 0.3339 0.078 Uiso 1 calc R . . C11B C 0.4975(18) -0.19226(18) 0.1738(9) 0.053(2) Uani 1 d . . . C10B C 0.3395(16) -0.17499(19) 0.2347(8) 0.048(2) Uani 1 d . . . C16B C 0.4486(19) -0.1943(2) 0.0433(8) 0.061(3) Uani 1 d . . . H16B H 0.3168 -0.1847 -0.0072 0.073 Uiso 1 calc R . . C15B C 0.597(2) -0.2105(2) -0.0119(10) 0.072(3) Uani 1 d . . . H15B H 0.5664 -0.2113 -0.1000 0.086 Uiso 1 calc R . . BR14B Br 0.9718(3) -0.24858(3) -0.02273(16) 0.0987(6) Uani 1 d . . . C9B C 0.1609(15) -0.15380(18) 0.1683(8) 0.049(2) Uani 1 d . . . H9B H 0.0325 -0.1610 0.0976 0.058 Uiso 1 calc R . . C8B C 0.3043(17) -0.13008(18) 0.1286(8) 0.048(2) Uani 1 d . . . C2B C 0.0544(17) -0.1440(2) 0.2777(8) 0.052(2) Uani 1 d . . . H2B H -0.1255 -0.1475 0.2599 0.063 Uiso 1 calc R . . O1B O 0.1839(12) -0.15871(15) 0.3894(6) 0.0678(19) Uani 1 d . . . N11B N 0.3558(16) -0.17677(18) 0.3549(9) 0.067(2) Uani 1 d . . . C3B C 0.1055(16) -0.1138(2) 0.2967(9) 0.056(3) Uani 1 d . . . H3B H 0.1841 -0.1097 0.3857 0.067 Uiso 1 calc R . . C7B C 0.2758(14) -0.10558(18) 0.2091(8) 0.047(2) Uani 1 d . . . H7B H 0.4377 -0.0989 0.2573 0.056 Uiso 1 calc R . . O4B O -0.1208(12) -0.09852(16) 0.2531(8) 0.081(2) Uani 1 d . . . C6B C 0.1247(17) -0.08403(19) 0.1313(9) 0.052(2) Uani 1 d . . . N5B N -0.0898(14) -0.08058(17) 0.1547(8) 0.063(2) Uani 1 d . . . C61B C 0.207(2) -0.0681(2) 0.0314(11) 0.073(3) Uani 1 d . . . H61C H 0.3661 -0.0597 0.0696 0.088 Uiso 1 calc R . . H61D H 0.2343 -0.0803 -0.0337 0.088 Uiso 1 calc R . . C62B C 0.028(3) -0.0466(3) -0.0309(13) 0.096(4) Uani 1 d . . . H62D H 0.0370 -0.0317 0.0260 0.116 Uiso 1 calc R . . H62E H -0.1391 -0.0537 -0.0509 0.116 Uiso 1 calc R . . H62F H 0.0702 -0.0408 -0.1075 0.116 Uiso 1 calc R . . O81B O 0.4134(16) -0.13045(14) 0.0454(7) 0.078(2) Uani 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 C2A 0.044(6) 0.080(7) 0.044(6) 0.005(5) 0.005(4) -0.006(5) O1A 0.038(4) 0.110(6) 0.062(5) 0.016(4) 0.022(3) 0.011(4) N11A 0.048(5) 0.077(6) 0.075(6) 0.015(5) 0.013(4) 0.010(4) C10A 0.030(5) 0.060(5) 0.043(5) -0.007(4) 0.004(4) -0.003(4) C9A 0.035(5) 0.069(6) 0.047(6) -0.006(4) 0.005(4) 0.001(4) C8A 0.052(6) 0.065(6) 0.054(7) 0.015(5) 0.011(5) 0.016(5) O81A 0.126(7) 0.081(5) 0.047(4) 0.012(4) 0.048(5) 0.019(4) C7A 0.038(5) 0.073(6) 0.027(5) 0.005(4) 0.003(4) -0.004(4) N5A 0.077(6) 0.086(6) 0.031(5) 0.003(4) 0.018(4) 0.016(5) O4A 0.072(5) 0.114(6) 0.038(4) 0.002(4) -0.001(3) 0.033(4) C3A 0.032(5) 0.096(8) 0.038(5) 0.006(5) 0.009(4) 0.009(5) C6A 0.052(6) 0.070(6) 0.042(6) 0.000(5) 0.018(5) -0.008(5) C61A 0.080(8) 0.072(7) 0.067(8) 0.003(6) 0.013(6) 0.004(6) C62A 0.117(11) 0.090(9) 0.097(10) 0.003(8) 0.027(8) 0.019(8) C13 0.056(7) 0.083(8) 0.100(9) 0.020(7) 0.013(6) 0.025(6) C12A 0.058(7) 0.069(7) 0.079(8) 0.003(6) 0.017(6) 0.000(5) C11A 0.023(4) 0.056(5) 0.074(7) 0.000(5) 0.010(4) 0.001(4) C16A 0.036(5) 0.066(6) 0.070(7) 0.003(5) 0.003(5) 0.012(5) C15A 0.060(6) 0.056(6) 0.055(6) 0.008(5) 0.001(5) 0.005(5) C14A 0.062(7) 0.055(6) 0.073(7) 0.006(5) 0.005(5) -0.012(5) BR14A 0.1240(13) 0.0934(10) 0.0975(11) 0.0380(8) 0.0095(8) 0.0005(8) C14B 0.065(7) 0.048(6) 0.085(9) -0.001(5) 0.025(6) 0.002(5) C13B 0.066(7) 0.071(7) 0.063(8) 0.003(5) 0.004(5) 0.011(6) C12B 0.069(7) 0.065(6) 0.054(7) 0.005(5) 0.002(5) 0.003(6) C11B 0.053(6) 0.053(5) 0.050(6) 0.010(4) 0.008(5) -0.003(5) C10B 0.035(5) 0.067(6) 0.037(5) 0.012(4) 0.000(4) -0.001(4) C16B 0.067(7) 0.078(7) 0.032(5) 0.003(5) 0.000(5) 0.020(5) C15B 0.089(8) 0.067(7) 0.053(7) 0.008(5) 0.005(6) 0.007(6) BR14B 0.0999(11) 0.0841(9) 0.1236(13) -0.0036(8) 0.0494(9) 0.0151(7) C9B 0.033(5) 0.070(6) 0.041(5) -0.004(4) 0.004(4) -0.010(4) C8B 0.048(5) 0.055(5) 0.038(5) 0.006(4) 0.003(4) 0.013(4) C2B 0.040(5) 0.081(7) 0.032(5) 0.008(4) 0.002(4) -0.008(5) O1B 0.065(4) 0.107(5) 0.033(4) 0.011(4) 0.015(3) 0.017(4) N11B 0.062(6) 0.078(6) 0.059(6) 0.009(4) 0.008(4) 0.007(5) C3B 0.037(5) 0.092(7) 0.040(6) -0.002(5) 0.012(4) 0.004(5) C7B 0.021(4) 0.071(6) 0.044(5) -0.001(4) 0.000(4) 0.007(4) O4B 0.051(4) 0.098(6) 0.102(6) 0.028(5) 0.037(4) 0.025(4) C6B 0.047(6) 0.067(6) 0.044(6) -0.002(4) 0.015(4) 0.002(5) N5B 0.045(5) 0.074(6) 0.065(6) 0.007(4) 0.004(4) 0.012(4) C61B 0.078(8) 0.079(7) 0.071(8) 0.014(6) 0.034(6) 0.017(6) C62B 0.101(10) 0.083(9) 0.102(11) 0.021(7) 0.018(8) 0.001(7) O81B 0.112(6) 0.072(5) 0.069(5) 0.002(4) 0.056(5) 0.007(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 C2A O1A 1.486(11) . ? C2A C3A 1.496(14) . ? C2A C9A 1.522(13) . ? O1A N11A 1.405(10) . ? N11A C10A 1.281(11) . ? C10A C9A 1.513(12) . ? C10A C11A 1.496(13) . ? C9A C8A 1.550(13) . ? C8A O81A 1.199(11) . ? C8A C7A 1.534(13) . ? C7A C6A 1.494(13) . ? C7A C3A 1.521(12) . ? N5A C6A 1.278(12) . ? N5A O4A 1.433(10) . ? O4A C3A 1.442(11) . ? C6A C61A 1.487(14) . ? C61A C62A 1.542(16) . ? C13 C12A 1.388(15) . ? C13 C14A 1.382(15) . ? C12A C11A 1.405(14) . ? C11A C16A 1.358(13) . ? C16A C15A 1.389(13) . ? C15A C14A 1.381(14) . ? C14A BR14A 1.899(10) . ? C14B C13B 1.368(15) . ? C14B C15B 1.374(15) . ? C14B BR14B 1.888(10) . ? C13B C12B 1.386(14) . ? C12B C11B 1.391(13) . ? C11B C16B 1.379(13) . ? C11B C10B 1.486(13) . ? C10B N11B 1.288(12) . ? C10B C9B 1.505(12) . ? C16B C15B 1.384(14) . ? C9B C2B 1.523(12) . ? C9B C8B 1.539(13) . ? C8B O81B 1.196(11) . ? C8B C7B 1.530(12) . ? C2B O1B 1.452(11) . ? C2B C3B 1.534(14) . ? O1B N11B 1.420(11) . ? C3B O4B 1.442(11) . ? C3B C7B 1.540(12) . ? C7B C6B 1.492(13) . ? O4B N5B 1.432(11) . ? C6B N5B 1.278(11) . ? C6B C61B 1.499(13) . ? C61B C62B 1.504(16) . ? 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 O1A C2A C3A 108.5(7) . . ? O1A C2A C9A 103.6(7) . . ? C3A C2A C9A 108.9(8) . . ? N11A O1A C2A 108.6(6) . . ? C10A N11A O1A 110.6(7) . . ? N11A C10A C9A 112.8(8) . . ? N11A C10A C11A 120.3(8) . . ? C9A C10A C11A 126.9(7) . . ? C10A C9A C2A 101.5(7) . . ? C10A C9A C8A 112.8(7) . . ? C2A C9A C8A 105.2(8) . . ? O81A C8A C7A 125.8(9) . . ? O81A C8A C9A 125.4(9) . . ? C7A C8A C9A 108.7(8) . . ? C6A C7A C3A 101.4(7) . . ? C6A C7A C8A 112.2(7) . . ? C3A C7A C8A 106.0(8) . . ? C6A N5A O4A 109.0(8) . . ? C3A O4A N5A 109.1(7) . . ? O4A C3A C2A 109.7(8) . . ? O4A C3A C7A 104.3(7) . . ? C2A C3A C7A 108.2(8) . . ? N5A C6A C61A 124.2(9) . . ? N5A C6A C7A 113.5(8) . . ? C61A C6A C7A 122.3(8) . . ? C6A C61A C62A 114.3(10) . . ? C12A C13 C14A 118.7(10) . . ? C13 C12A C11A 120.1(10) . . ? C16A C11A C12A 120.0(9) . . ? C16A C11A C10A 120.5(8) . . ? C12A C11A C10A 119.4(8) . . ? C11A C16A C15A 120.4(9) . . ? C14A C15A C16A 119.5(10) . . ? C15A C14A C13 121.2(10) . . ? C15A C14A BR14A 118.7(8) . . ? C13 C14A BR14A 120.0(8) . . ? C13B C14B C15B 118.9(10) . . ? C13B C14B BR14B 121.8(8) . . ? C15B C14B BR14B 119.3(9) . . ? C14B C13B C12B 119.8(10) . . ? C13B C12B C11B 121.4(10) . . ? C16B C11B C12B 118.3(9) . . ? C16B C11B C10B 120.3(8) . . ? C12B C11B C10B 121.3(9) . . ? N11B C10B C11B 120.1(8) . . ? N11B C10B C9B 114.4(8) . . ? C11B C10B C9B 125.4(8) . . ? C15B C16B C11B 119.6(9) . . ? C16B C15B C14B 121.9(10) . . ? C10B C9B C2B 100.5(7) . . ? C10B C9B C8B 110.6(7) . . ? C2B C9B C8B 106.8(7) . . ? O81B C8B C7B 125.4(9) . . ? O81B C8B C9B 125.7(8) . . ? C7B C8B C9B 108.9(7) . . ? O1B C2B C9B 106.4(7) . . ? O1B C2B C3B 110.2(7) . . ? C9B C2B C3B 109.1(7) . . ? N11B O1B C2B 109.2(7) . . ? C10B N11B O1B 109.4(8) . . ? O4B C3B C2B 110.8(8) . . ? O4B C3B C7B 105.3(7) . . ? C2B C3B C7B 107.3(7) . . ? C6B C7B C8B 111.7(7) . . ? C6B C7B C3B 101.5(7) . . ? C8B C7B C3B 107.5(8) . . ? N5B O4B C3B 109.1(6) . . ? N5B C6B C7B 113.8(8) . . ? N5B C6B C61B 121.7(9) . . ? C7B C6B C61B 124.5(8) . . ? C6B N5B O4B 110.1(7) . . ? C62B C61B C6B 114.9(9) . . ? _refine_diff_density_max 0.513 _refine_diff_density_min -0.536 _refine_diff_density_rms 0.088 _publ_section_references ; Kabsch, W. (1988), J.Appl.Cryst 21 916-932. Sheldrick, G.M. (1990) SHELX86, Acta Cryst. A46 467-480. Sheldrick, G.M. (1993) SHELXL program for crystallography refinement. University of Gottingen, Germany. Spek, A.L., (1994) PLATON-94 program, Utrecht University, The Netherlands Walker, N. and Stuart, D., Acta Crystl 1983 A39 158. ;