data_ih03 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C15 H33 N, Br' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C15 H33 Br N' _chemical_formula_weight 307.33 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.971(3) _cell_length_b 8.667(2) _cell_length_c 15.737(2) _cell_angle_alpha 80.810(10) _cell_angle_beta 88.21(2) _cell_angle_gamma 66.44(2) _cell_volume 859.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.187 _exptl_crystal_density_method ? _exptl_crystal_F_000 330 _exptl_absorpt_coefficient_mu 3.104 _exptl_absorpt_correction_type 'empirical method psi scan' _exptl_absorpt_correction_T_min 0.793 _exptl_absorpt_correction_T_max 0.998 _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2870 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 65.40 _reflns_number_total 2863 _reflns_number_observed 2655 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0923P)^2^+0.6343P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2862 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_obs 0.0471 _refine_ls_wR_factor_all 0.1442 _refine_ls_wR_factor_obs 0.1384 _refine_ls_goodness_of_fit_all 1.034 _refine_ls_goodness_of_fit_obs 1.043 _refine_ls_restrained_S_all 1.046 _refine_ls_restrained_S_obs 1.043 _refine_ls_shift/esd_max 0.002 _refine_ls_shift/esd_mean 0.001 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Br1 Br 0.38586(6) 0.77937(5) 0.39857(2) 0.0663(2) Uani 1 d . . N2 N 0.0666(4) 1.3006(3) 0.4456(2) 0.0445(6) Uani 1 d . . C3 C 0.1526(6) 1.1612(4) 0.5218(2) 0.0539(8) Uani 1 d . . H3A H 0.2458(6) 1.1858(4) 0.5557(2) 0.081 Uiso 1 calc R . H3B H 0.2274(6) 1.0544(4) 0.5021(2) 0.081 Uiso 1 calc R . H3C H 0.0393(6) 1.1544(4) 0.5564(2) 0.081 Uiso 1 calc R . C4 C -0.0782(6) 1.2555(4) 0.3949(2) 0.0588(8) Uani 1 d . . H4A H -0.1363(6) 1.3421(4) 0.3456(2) 0.088 Uiso 1 calc R . H4B H -0.1893(6) 1.2478(4) 0.4306(2) 0.088 Uiso 1 calc R . H4C H -0.0013(6) 1.1478(4) 0.3764(2) 0.088 Uiso 1 calc R . C5 C -0.0640(5) 1.4682(4) 0.4750(2) 0.0465(7) Uani 1 d . . H5A H -0.1733(5) 1.4544(4) 0.5111(2) 0.056 Uiso 1 calc R . H5B H -0.1310(5) 1.5531(4) 0.4251(2) 0.056 Uiso 1 calc R . C6 C 0.2492(5) 1.3049(4) 0.3918(2) 0.0497(7) Uani 1 d . . H6A H 0.3454(5) 1.3240(4) 0.4278(2) 0.060 Uiso 1 calc R . H6B H 0.3227(5) 1.1935(4) 0.3751(2) 0.060 Uiso 1 calc R . C7 C 0.1943(6) 1.4379(5) 0.3113(2) 0.0639(9) Uani 1 d . . H7A H 0.1076(6) 1.4152(5) 0.2721(2) 0.077 Uiso 1 calc R . H7B H 0.1154(6) 1.5500(5) 0.3263(2) 0.077 Uiso 1 calc R . C8 C 0.3889(6) 1.4347(5) 0.2682(3) 0.0666(10) Uani 1 d . . H8A H 0.4670(6) 1.3206(5) 0.2555(3) 0.080 Uiso 1 calc R . H8B H 0.4738(6) 1.4556(5) 0.3089(3) 0.080 Uiso 1 calc R . C9 C 0.3633(8) 1.5581(7) 0.1867(3) 0.0830(13) Uani 1 d . . H9A H 0.2960(8) 1.5271(7) 0.1432(3) 0.100 Uiso 1 calc R . H9B H 0.2690(8) 1.6706(7) 0.1972(3) 0.100 Uiso 1 calc R . C10 C 0.5555(7) 1.5697(6) 0.1513(3) 0.0795(12) Uani 1 d . . H10A H 0.6173(7) 1.6054(6) 0.1947(3) 0.095 Uiso 1 calc R . H10B H 0.6517(7) 1.4548(6) 0.1454(3) 0.095 Uiso 1 calc R . C11 C 0.5518(9) 1.6784(9) 0.0700(3) 0.102(2) Uani 1 d . . H11A H 0.4981(9) 1.6383(9) 0.0259(3) 0.122 Uiso 1 calc R . H11B H 0.4496(9) 1.7920(9) 0.0745(3) 0.122 Uiso 1 calc R . C12 C 0.7395(8) 1.6958(6) 0.0382(3) 0.0845(13) Uani 1 d . . H12A H 0.8416(8) 1.5811(6) 0.0357(3) 0.101 Uiso 1 calc R . H12B H 0.7909(8) 1.7367(6) 0.0827(3) 0.101 Uiso 1 calc R . C13 C 0.7507(10) 1.7992(9) -0.0428(3) 0.109(2) Uani 1 d . . H13A H 0.7112(10) 1.7528(9) -0.0883(3) 0.131 Uiso 1 calc R . H13B H 0.6422(10) 1.9123(9) -0.0427(3) 0.131 Uiso 1 calc R . C14 C 0.9389(8) 1.8215(6) -0.0686(3) 0.0866(13) Uani 1 d . . H14A H 1.0461(8) 1.7076(6) -0.0680(3) 0.104 Uiso 1 calc R . H14B H 0.9775(8) 1.8664(6) -0.0223(3) 0.104 Uiso 1 calc R . C15 C 0.9631(9) 1.9220(9) -0.1476(3) 0.101(2) Uani 1 d . . H15A H 0.9340(9) 1.8727(9) -0.1943(3) 0.122 Uiso 1 calc R . H15B H 0.8511(9) 2.0344(9) -0.1503(3) 0.122 Uiso 1 calc R . C16 C 1.1474(10) 1.9482(8) -0.1686(4) 0.103(2) Uani 1 d . . H16A H 1.2588(10) 1.8356(8) -0.1665(4) 0.124 Uiso 1 calc R . H16B H 1.1773(10) 1.9959(8) -0.1214(4) 0.124 Uiso 1 calc R . C17 C 1.1732(10) 2.0498(8) -0.2469(4) 0.104(2) Uani 1 d . . H17A H 1.3113(10) 2.0489(8) -0.2465(4) 0.156 Uiso 1 calc R . H17B H 1.0712(10) 2.1649(8) -0.2504(4) 0.156 Uiso 1 calc R . H17C H 1.1543(10) 2.0030(8) -0.2957(4) 0.156 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 Br1 0.0566(3) 0.0720(3) 0.0751(3) -0.0182(2) 0.0064(2) -0.0285(2) N2 0.0451(14) 0.0414(12) 0.0475(13) -0.0053(10) 0.0041(10) -0.0189(10) C3 0.064(2) 0.0421(15) 0.054(2) 0.0027(13) 0.0048(15) -0.0230(14) C4 0.064(2) 0.058(2) 0.062(2) -0.010(2) -0.001(2) -0.032(2) C5 0.043(2) 0.0419(14) 0.053(2) -0.0074(12) 0.0053(13) -0.0155(12) C6 0.050(2) 0.045(2) 0.051(2) -0.0072(13) 0.0114(13) -0.0173(13) C7 0.064(2) 0.072(2) 0.053(2) 0.004(2) 0.005(2) -0.030(2) C8 0.070(2) 0.057(2) 0.067(2) -0.004(2) 0.022(2) -0.022(2) C9 0.089(3) 0.101(3) 0.060(2) 0.010(2) 0.007(2) -0.048(3) C10 0.076(3) 0.074(3) 0.077(3) 0.005(2) 0.023(2) -0.026(2) C11 0.094(4) 0.137(5) 0.075(3) 0.022(3) 0.009(2) -0.062(3) C12 0.083(3) 0.080(3) 0.080(3) 0.008(2) 0.021(2) -0.031(2) C13 0.100(4) 0.150(5) 0.078(3) 0.026(3) 0.011(3) -0.069(4) C14 0.084(3) 0.084(3) 0.083(3) 0.007(2) 0.021(2) -0.033(2) C15 0.092(4) 0.133(5) 0.076(3) 0.026(3) 0.004(2) -0.058(3) C16 0.102(4) 0.108(4) 0.088(3) 0.015(3) 0.021(3) -0.043(3) C17 0.106(4) 0.115(4) 0.087(3) 0.015(3) 0.021(3) -0.052(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N2 C3 1.504(4) . ? N2 C4 1.508(4) . ? N2 C5 1.512(4) . ? N2 C6 1.516(4) . ? C5 C5 1.514(6) 2_586 ? C6 C7 1.515(4) . ? C7 C8 1.490(5) . ? C8 C9 1.497(5) . ? C9 C10 1.469(6) . ? C10 C11 1.457(6) . ? C11 C12 1.441(7) . ? C12 C13 1.456(6) . ? C13 C14 1.438(7) . ? C14 C15 1.446(6) . ? C15 C16 1.412(8) . ? C16 C17 1.447(6) . ? 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 C3 N2 C4 107.2(2) . . ? C3 N2 C5 110.5(2) . . ? C4 N2 C5 107.0(2) . . ? C3 N2 C6 107.9(2) . . ? C4 N2 C6 110.3(2) . . ? C5 N2 C6 113.7(2) . . ? N2 C5 C5 112.7(3) . 2_586 ? C7 C6 N2 116.0(3) . . ? C8 C7 C6 110.1(3) . . ? C7 C8 C9 117.2(4) . . ? C10 C9 C8 116.5(4) . . ? C11 C10 C9 121.6(4) . . ? C12 C11 C10 121.0(5) . . ? C11 C12 C13 124.6(5) . . ? C14 C13 C12 122.3(5) . . ? C13 C14 C15 125.8(5) . . ? C16 C15 C14 124.1(5) . . ? C15 C16 C17 124.7(6) . . ? 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 C3 N2 C5 C5 65.3(4) . . . 2_586 ? C4 N2 C5 C5 -178.3(3) . . . 2_586 ? C6 N2 C5 C5 -56.2(4) . . . 2_586 ? C3 N2 C6 C7 179.9(3) . . . . ? C4 N2 C6 C7 63.1(4) . . . . ? C5 N2 C6 C7 -57.2(4) . . . . ? N2 C6 C7 C8 176.4(3) . . . . ? C6 C7 C8 C9 179.6(4) . . . . ? C7 C8 C9 C10 172.0(4) . . . . ? C8 C9 C10 C11 176.7(5) . . . . ? C9 C10 C11 C12 176.6(6) . . . . ? C10 C11 C12 C13 178.9(6) . . . . ? C11 C12 C13 C14 175.6(6) . . . . ? C12 C13 C14 C15 -179.8(6) . . . . ? C13 C14 C15 C16 176.5(7) . . . . ? C14 C15 C16 C17 -179.3(7) . . . . ? _refine_diff_density_max 0.645 _refine_diff_density_min -0.596 _refine_diff_density_rms 0.071 #===END data_ih129a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H37 Br N2 O3' _chemical_formula_weight 397.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2410(10) _cell_length_b 9.3560(10) _cell_length_c 14.2810(10) _cell_angle_alpha 74.423(10) _cell_angle_beta 85.333(10) _cell_angle_gamma 71.042(10) _cell_volume 1003.11(18) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 2.852 _exptl_absorpt_correction_type 'empirical method psi scan' _exptl_absorpt_correction_T_min 0.4816 _exptl_absorpt_correction_T_max 0.8475 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1614 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1393 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 5.17 _diffrn_reflns_theta_max 45.65 _reflns_number_total 1614 _reflns_number_gt 864 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.1885P)^2^+3.3813P] 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 0.0000(11) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1614 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2056 _refine_ls_R_factor_gt 0.1121 _refine_ls_wR_factor_ref 0.3217 _refine_ls_wR_factor_gt 0.2584 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.810 _refine_ls_shift/su_mean 0.005 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 0.751(3) 0.545(2) 0.2002(16) 0.131(9) Uani 1 1 d . . . H1A H 0.7443 0.4856 0.2634 0.157 Uiso 1 1 calc R . . H1B H 0.6894 0.6506 0.1825 0.157 Uiso 1 1 calc R . . C2 C 0.841(2) 0.4816(17) 0.1395(14) 0.080(5) Uani 1 1 d . . . H2 H 0.8439 0.5441 0.0770 0.096 Uiso 1 1 calc R . . C3 C 0.944(3) 0.313(2) 0.1596(18) 0.104(7) Uani 1 1 d . . . O4 O 0.947(2) 0.2222(15) 0.2369(12) 0.128(6) Uani 1 1 d . . . O5 O 1.0309(15) 0.2677(11) 0.0833(8) 0.090(4) Uani 1 1 d . . . C6 C 1.129(2) 0.1077(17) 0.0942(13) 0.089(6) Uani 1 1 d . . . H6A H 1.0556 0.0426 0.1178 0.107 Uiso 1 1 calc R . . H6B H 1.2199 0.0774 0.1413 0.107 Uiso 1 1 calc R . . C7 C 1.202(2) 0.0846(19) -0.0001(11) 0.098(6) Uani 1 1 d . . . H7A H 1.2764 0.1488 -0.0226 0.117 Uiso 1 1 calc R . . H7B H 1.1102 0.1188 -0.0473 0.117 Uiso 1 1 calc R . . C8 C 1.307(2) -0.0892(16) 0.0059(11) 0.088(6) Uani 1 1 d . . . H8A H 1.3981 -0.1234 0.0537 0.106 Uiso 1 1 calc R . . H8B H 1.2324 -0.1530 0.0281 0.106 Uiso 1 1 calc R . . C9 C 1.386(3) -0.1154(19) -0.0910(12) 0.102(7) Uani 1 1 d . . . H9A H 1.4601 -0.0514 -0.1132 0.123 Uiso 1 1 calc R . . H9B H 1.2945 -0.0812 -0.1387 0.123 Uiso 1 1 calc R . . C10 C 1.489(2) -0.2866(16) -0.0851(11) 0.083(6) Uani 1 1 d . . . H10A H 1.5812 -0.3203 -0.0380 0.099 Uiso 1 1 calc R . . H10B H 1.4151 -0.3508 -0.0620 0.099 Uiso 1 1 calc R . . C11 C 1.565(2) -0.3132(16) -0.1807(12) 0.084(6) Uani 1 1 d . . . H11A H 1.6322 -0.2435 -0.2062 0.101 Uiso 1 1 calc R . . H11B H 1.4724 -0.2868 -0.2265 0.101 Uiso 1 1 calc R . . C12 C 1.679(3) -0.4815(17) -0.1732(12) 0.103(7) Uani 1 1 d . . . H12A H 1.6096 -0.5505 -0.1511 0.124 Uiso 1 1 calc R . . H12B H 1.7671 -0.5096 -0.1247 0.124 Uiso 1 1 calc R . . C13 C 1.766(2) -0.5080(15) -0.2715(11) 0.075(5) Uani 1 1 d . . . H13A H 1.6771 -0.4870 -0.3184 0.090 Uiso 1 1 calc R . . H13B H 1.8274 -0.4330 -0.2960 0.090 Uiso 1 1 calc R . . C14 C 1.888(2) -0.6689(17) -0.2643(11) 0.077(5) Uani 1 1 d . . . H14A H 1.8300 -0.7443 -0.2336 0.092 Uiso 1 1 calc R . . H14B H 1.9832 -0.6858 -0.2224 0.092 Uiso 1 1 calc R . . C15 C 1.959(2) -0.6997(18) -0.3601(10) 0.083(5) Uani 1 1 d . . . H15A H 1.8652 -0.6881 -0.4012 0.100 Uiso 1 1 calc R . . H15B H 2.0141 -0.6224 -0.3923 0.100 Uiso 1 1 calc R . . C16 C 2.086(2) -0.8601(16) -0.3486(10) 0.088(6) Uani 1 1 d . . . H16A H 2.0436 -0.9323 -0.2989 0.106 Uiso 1 1 calc R . . H16B H 2.1923 -0.8596 -0.3239 0.106 Uiso 1 1 calc R . . N17 N 2.131(2) -0.9267(14) -0.4381(9) 0.083(5) Uani 1 1 d . . . C18 C 2.177(2) -0.8062(19) -0.5199(13) 0.095(6) Uani 1 1 d . . . H18A H 2.2755 -0.7862 -0.5012 0.142 Uiso 1 1 calc R . . H18B H 2.0823 -0.7110 -0.5334 0.142 Uiso 1 1 calc R . . H18C H 2.2037 -0.8448 -0.5770 0.142 Uiso 1 1 calc R . . C19 C 2.295(2) -1.0672(18) -0.4155(12) 0.084(6) Uani 1 1 d . . . H19A H 2.3871 -1.0335 -0.4020 0.127 Uiso 1 1 calc R . . H19B H 2.3245 -1.1112 -0.4704 0.127 Uiso 1 1 calc R . . H19C H 2.2769 -1.1448 -0.3599 0.127 Uiso 1 1 calc R . . C20 C 1.980(2) -0.9654(18) -0.4600(11) 0.072(5) Uani 1 1 d . . . H20A H 1.9515 -1.0376 -0.4036 0.086 Uiso 1 1 calc R . . H20B H 1.8819 -0.8713 -0.4760 0.086 Uiso 1 1 calc R . . Br21 Br 2.5416(3) -0.8136(3) -0.35259(17) 0.1239(16) Uani 1 1 d . . . O22 O 2.320(3) -0.430(2) -0.4402(12) 0.174(9) Uani 0.85 1 d P . . 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 0.16(2) 0.099(15) 0.131(18) -0.066(15) 0.045(16) -0.021(14) C2 0.106(14) 0.047(11) 0.110(14) -0.033(10) 0.013(12) -0.049(10) C3 0.150(19) 0.077(16) 0.096(17) -0.028(14) 0.059(15) -0.056(13) O4 0.207(16) 0.063(8) 0.102(11) -0.018(8) 0.053(11) -0.042(9) O5 0.131(10) 0.051(7) 0.074(8) -0.010(6) 0.016(7) -0.019(7) C6 0.114(15) 0.060(12) 0.103(15) -0.031(10) 0.028(12) -0.039(11) C7 0.140(17) 0.091(14) 0.062(11) -0.021(10) 0.017(12) -0.039(12) C8 0.133(16) 0.051(10) 0.075(12) -0.020(8) -0.003(11) -0.019(10) C9 0.141(17) 0.091(14) 0.070(12) -0.032(10) 0.019(11) -0.026(12) C10 0.103(14) 0.068(11) 0.065(11) -0.018(9) 0.021(10) -0.016(10) C11 0.118(14) 0.056(10) 0.085(13) -0.025(9) -0.018(11) -0.025(10) C12 0.169(19) 0.062(11) 0.083(13) -0.026(10) 0.024(13) -0.042(11) C13 0.110(13) 0.052(10) 0.073(12) -0.020(8) 0.002(10) -0.034(10) C14 0.111(14) 0.071(12) 0.076(12) -0.025(9) 0.017(10) -0.064(11) C15 0.122(15) 0.081(12) 0.043(10) -0.016(9) 0.014(10) -0.033(11) C16 0.166(17) 0.048(10) 0.060(11) -0.023(8) 0.017(11) -0.044(10) N17 0.150(15) 0.051(8) 0.044(9) -0.004(7) 0.010(9) -0.033(9) C18 0.130(16) 0.079(13) 0.086(14) -0.036(11) 0.005(12) -0.036(11) C19 0.080(13) 0.069(11) 0.098(13) -0.027(9) 0.006(10) -0.013(10) C20 0.101(14) 0.077(11) 0.049(11) -0.014(8) 0.001(10) -0.046(10) Br21 0.138(2) 0.141(2) 0.129(2) -0.0853(17) 0.0315(15) -0.0580(15) O22 0.22(2) 0.141(15) 0.120(14) -0.012(12) -0.008(14) -0.022(14) _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 C1 C2 1.24(2) . ? C2 C3 1.49(2) . ? C3 O4 1.193(19) . ? C3 O5 1.34(2) . ? O5 C6 1.423(17) . ? C6 C7 1.47(2) . ? C7 C8 1.56(2) . ? C8 C9 1.53(2) . ? C9 C10 1.53(2) . ? C10 C11 1.50(2) . ? C11 C12 1.528(19) . ? C12 C13 1.57(2) . ? C13 C14 1.497(19) . ? C14 C15 1.506(19) . ? C15 C16 1.50(2) . ? C16 N17 1.536(18) . ? N17 C20 1.48(2) . ? N17 C18 1.51(2) . ? N17 C19 1.535(19) . ? C20 C20 1.43(3) 2_934 ? 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 C1 C2 C3 125(2) . . ? O4 C3 O5 121.8(17) . . ? O4 C3 C2 123.1(17) . . ? O5 C3 C2 115(2) . . ? C3 O5 C6 119.4(13) . . ? O5 C6 C7 109.6(14) . . ? C6 C7 C8 112.4(14) . . ? C9 C8 C7 113.2(13) . . ? C8 C9 C10 113.2(13) . . ? C11 C10 C9 113.3(12) . . ? C10 C11 C12 113.2(13) . . ? C11 C12 C13 113.5(13) . . ? C14 C13 C12 114.5(12) . . ? C13 C14 C15 114.7(13) . . ? C16 C15 C14 112.6(12) . . ? C15 C16 N17 118.5(12) . . ? C20 N17 C18 113.6(13) . . ? C20 N17 C19 114.1(13) . . ? C18 N17 C19 105.3(14) . . ? C20 N17 C16 107.4(14) . . ? C18 N17 C16 108.1(12) . . ? C19 N17 C16 108.2(12) . . ? C20 C20 N17 108.8(19) 2_934 . ? 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 C1 C2 C3 O4 1(3) . . . . ? C1 C2 C3 O5 179(2) . . . . ? O4 C3 O5 C6 0(3) . . . . ? C2 C3 O5 C6 -177.8(16) . . . . ? C3 O5 C6 C7 176.2(18) . . . . ? O5 C6 C7 C8 -178.5(15) . . . . ? C6 C7 C8 C9 -179.6(18) . . . . ? C7 C8 C9 C10 179.9(17) . . . . ? C8 C9 C10 C11 179.2(18) . . . . ? C9 C10 C11 C12 175.8(17) . . . . ? C10 C11 C12 C13 -176.9(16) . . . . ? C11 C12 C13 C14 175.7(15) . . . . ? C12 C13 C14 C15 174.2(16) . . . . ? C13 C14 C15 C16 177.6(15) . . . . ? C14 C15 C16 N17 162.7(16) . . . . ? C15 C16 N17 C20 -71.9(19) . . . . ? C15 C16 N17 C18 51(2) . . . . ? C15 C16 N17 C19 164.5(16) . . . . ? C18 N17 C20 C20 63(2) . . . 2_934 ? C19 N17 C20 C20 -57(2) . . . 2_934 ? C16 N17 C20 C20 -177.2(15) . . . 2_934 ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 45.65 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.871 _refine_diff_density_min -0.425 _refine_diff_density_rms 0.097 #===END