# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/442 data_global _audit_creation_method 'maXus' _publ_contact_author_name ' Alison Edwards' _publ_contact_author_email 'ajed@rsc.anu.edu.au' _publ_contact_author_fax ' australia + 2 6249 0750' _publ_contact_author_phone 'australia + 2 62494109' _publ_contact_author_address ; Research School of Chemistry, ANU, A.C.T., 0200 Australia ; _chemical_compound_source 'Local laboratory' _exptl_crystal_description 'prism' _exptl_crystal_colour 'Colourless' _cell_measurement_temperature 200 _refine_ls_hydrogen_treatment 'noref' # Submission details _publ_requested_journal 'test ' # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.010 0 0 -1 0.055 1 0 0 0.035 -1 0 0 0.070 0 1 0 0.100 -1 1 0 0.090 0 -1 0 0.055 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.748 _exptl_absorpt_correction_T_max 0.873 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_reflns_av_R_equivalents 0.048 _exptl_absorpt_coefficient_mu 2.11 _exptl_crystal_F_000 404 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 'Waasmaier & Kirfel, 1995' 'H ' 'H ' 0.0000 0.0000 'Waasmaier & Kirfel, 1995' 'Br' 'Br' -0.2901 2.4595 'Waasmaier & Kirfel, 1995' 'N ' 'N ' 0.0061 0.0033 'Waasmaier & Kirfel, 1995' 'O ' 'O ' 0.0106 0.0060 'Waasmaier & Kirfel, 1995' _diffrn_measurement_device 'KappaCCD' _computing_data_collection 'KappaCCD' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 384.358 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz '+X,+Y,+Z' '-X,+Y+ 1/2,-Z' _symmetry_space_group_name_H-M 'P 21 ' _symmetry_cell_setting 'Monoclinic' _chemical_formula_moiety 'C19 H30 Br N O2 ' _chemical_formula_sum 'C19 H30 Br N O2 ' _chemical_name_systematic ; ? ; _cell_length_a 8.4008(5) _cell_length_b 9.9077(6) _cell_length_c 11.8739(8) _cell_angle_alpha 90.00 _cell_angle_beta 97.278(4) _cell_angle_gamma 90.00 _cell_volume 980.3(5) _diffrn_reflns_number 9089 _diffrn_reflns_theta_max 25.03 _cell_measurement_reflns_used 9117 _cell_measurement_theta_min 2.546 _cell_measurement_theta_max 25.028 _reflns_number_total 3263 _reflns_number_gt 2453 _reflns_threshold_expression 'I> 3.00 sigma(I)' _reflns_d_resolution_low 1.79 _reflns_d_resolution_high 0.65 _reflns_limit_h_max 10 _reflns_limit_h_min -9 _reflns_limit_k_max 11 _reflns_limit_k_min 0 _reflns_limit_l_max 14 _reflns_limit_l_min -14 _reflns_Friedel_coverage 0.775 _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_matrix_type full _refine_ls_R_factor_all 0.062 _refine_ls_wR_factor_all 0.064 _refine_ls_R_factor_gt 0.042 _refine_ls_wR_factor_gt 0.045 _refine_ls_wR_factor_ref 0.063 _refine_ls_goodness_of_fit_gt 1.129 _refine_ls_goodness_of_fit_ref 1.129 _refine_ls_goodness_of_fit_all 1.179 _refine_ls_number_parameters 203 _refine_ls_number_reflns 2453 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_abs_structure_Rogers 1.03 _refine_ls_abs_structure_details ; 1425 Friedel equivalents measured clearly showing via the Rogers parameter that the absolute structure is as reported. This is in accord with the known absolute structure of the menthyl group used in the synthesis. ; _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme sigma _refine_ls_weighting_details ; w = 1 / ( s^2^(Fo^2^) + 0.03000 * Fo^2^) ; _refine_ls_extinction_method none _refine_ls_extinction_coef ? _computing_structure_refinement 'maxus(Mackay et al., 1999)' _computing_molecular_graphics 'Ortep (Johnson, 1976)' _computing_publication_material 'maxus(Mackay et al., 1999)' _atom_sites_solution_hydrogens geom _refine_diff_density_max 0.40 _refine_diff_density_min -0.44 _refine_diff_density_rms 0.06 #================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type Br1 1.20043(3) 0.360000 0.94106(3) 0.0958(3) 1.00 Uij O11 0.9555(2) 0.4716(2) 0.6576(1) 0.056(1) 1.00 Uij O22 0.8395(3) 0.6621(2) 0.7137(2) 0.070(1) 1.00 Uij N2 0.8304(3) 0.4667(3) 0.8133(2) 0.0537(6) 1.00 Uiso C13 1.1179(3) 0.4666(3) 0.5048(2) 0.055(2) 1.00 Uij C10 0.8735(3) 0.5448(3) 0.7269(2) 0.055(2) 1.00 Uij C12 0.9769(3) 0.5355(3) 0.5490(2) 0.054(2) 1.00 Uij C17 0.8224(3) 0.5209(3) 0.4701(2) 0.059(2) 1.00 Uij C18 1.2744(4) 0.4762(3) 0.5883(3) 0.069(2) 1.00 Uij C9 0.7262(4) 0.2405(3) 0.8384(3) 0.062(2) 1.00 Uij C4 0.6041(4) 0.4380(4) 0.9205(3) 0.072(2) 1.00 Uij C16 0.8363(4) 0.5731(3) 0.3505(2) 0.063(2) 1.00 Uij C15 0.9777(4) 0.5058(3) 0.3085(2) 0.067(2) 1.00 Uij C5 0.6441(4) 0.2887(4) 0.9385(3) 0.069(2) 1.00 Uij C1 0.8782(3) 0.3261(3) 0.8336(2) 0.056(2) 1.00 Uij C14 1.1315(4) 0.5225(3) 0.3848(3) 0.067(2) 1.00 Uij C8 0.9808(3) 0.3151(3) 0.9456(3) 0.057(1) 1.00 Uij C3 0.7423(4) 0.5275(3) 0.9004(3) 0.059(2) 1.00 Uij C21 0.6786(5) 0.5549(4) 0.2742(3) 0.091(2) 1.00 Uij C6 0.7543(4) 0.2602(3) 1.0480(3) 0.074(2) 1.00 Uij C19 1.4088(4) 0.3942(4) 0.5450(3) 0.095(2) 1.00 Uij C7 0.9287(4) 0.2854(3) 1.0412(3) 0.064(2) 1.00 Uij C20 1.3290(5) 0.6188(4) 0.6159(4) 0.102(3) 1.00 Uij H13 1.092994 0.372191 0.496855 0.065000 1.00 Uiso H12 1.000749 0.629390 0.562678 0.063884 1.00 Uiso H17A 0.739055 0.569384 0.501073 0.068709 1.00 Uiso H17B 0.796155 0.426584 0.465972 0.068709 1.00 Uiso H18 1.250293 0.437206 0.658231 0.078402 1.00 Uiso H9A 0.656766 0.248414 0.767981 0.071982 1.00 Uiso H9B 0.756966 0.147914 0.850781 0.071982 1.00 Uiso H16 0.858727 0.668064 0.354331 0.072102 1.00 Uiso H15A 0.987930 0.542597 0.234978 0.076976 1.00 Uiso H15B 0.952430 0.411498 0.301378 0.076976 1.00 Uiso H5 0.545282 0.240239 0.939176 0.079122 1.00 Uiso H1 0.937266 0.297572 0.773788 0.066459 1.00 Uiso H14A 1.215577 0.475872 0.353176 0.077358 1.00 Uiso H14B 1.156977 0.616772 0.391577 0.077358 1.00 Uiso H3A 0.701162 0.614073 0.874959 0.069610 1.00 Uiso H3B 0.812962 0.537873 0.969959 0.069610 1.00 Uiso H21A 0.595172 0.601367 0.306766 0.099781 1.00 Uiso H21B 0.652672 0.460667 0.267066 0.099781 1.00 Uiso H21C 0.688072 0.591667 0.200566 0.099781 1.00 Uiso H19A 1.372705 0.303798 0.527593 0.104944 1.00 Uiso H19B 1.500805 0.391998 0.601893 0.104944 1.00 Uiso H19C 1.437305 0.436399 0.477493 0.104944 1.00 Uiso H7 1.004186 0.279524 1.108853 0.073805 1.00 Uiso H20A 1.242406 0.666591 0.643539 0.110353 1.00 Uiso H20B 1.356906 0.662691 0.549139 0.110353 1.00 Uiso H20C 1.420406 0.618291 0.673439 0.110353 1.00 Uiso H6A 0.738483 0.167388 1.066918 0.085037 1.00 Uiso H6B 0.719683 0.317188 1.105718 0.085037 1.00 Uiso H4A 0.561355 0.467264 0.987627 0.081821 1.00 Uiso H4B 0.521855 0.443064 0.856627 0.081821 1.00 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br1 0.0547(2) 0.0866(2) 0.1440(3) -.0022(2) 0.0075(2) 0.0202(3) O11 0.073(1) 0.048(1) 0.049(1) 0.0076(9) 0.0222(9) 0.0094(9) O22 0.099(2) 0.048(1) 0.063(1) 0.011(1) 0.014(1) 0.006(1) C13 0.059(2) 0.053(2) 0.053(2) -.002(1) 0.013(1) 0.013(1) C10 0.058(2) 0.061(2) 0.043(2) -.001(1) 0.000(1) 0.001(1) C12 0.063(2) 0.046(2) 0.052(2) 0.001(1) 0.010(1) 0.010(1) C17 0.063(2) 0.055(2) 0.058(2) 0.005(1) 0.010(1) -.002(1) C18 0.059(2) 0.074(2) 0.073(2) -.005(2) 0.010(2) 0.016(2) C9 0.069(2) 0.061(2) 0.056(2) -.006(2) 0.007(2) -.017(2) C4 0.062(2) 0.078(3) 0.075(2) 0.003(2) 0.021(2) -.005(2) C16 0.078(2) 0.057(2) 0.051(2) 0.002(1) 0.003(2) -.002(2) C15 0.091(2) 0.063(2) 0.047(2) -.001(2) 0.015(2) 0.004(1) C5 0.064(2) 0.070(2) 0.073(2) -.010(2) 0.018(2) 0.000(2) C1 0.062(2) 0.058(2) 0.049(2) 0.007(1) 0.018(1) 0.003(1) C14 0.072(2) 0.072(2) 0.058(2) 0.001(2) 0.018(2) 0.009(2) C8 0.048(1) 0.051(2) 0.070(2) 0.002(1) 0.010(1) 0.008(1) C3 0.058(2) 0.059(2) 0.062(2) 0.009(1) 0.019(1) -.005(2) C21 0.104(3) 0.107(3) 0.059(2) 0.016(2) -.004(2) -.001(2) C6 0.092(2) 0.068(2) 0.065(2) 0.005(2) 0.040(2) 0.003(2) C19 0.069(2) 0.097(3) 0.119(3) 0.012(2) 0.015(2) 0.022(2) C7 0.075(2) 0.066(2) 0.050(2) 0.016(2) 0.006(2) 0.002(1) C20 0.092(3) 0.097(3) 0.112(3) -.014(2) -.022(2) 0.000(3) 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 C12 O11 C10 O22 -11.5(3) . . . . ? C12 O11 C10 N2 167.0(4) . . . . ? C10 O11 C12 C13 159.3(3) . . . . ? C10 O11 C12 C17 -78.5(3) . . . . ? C1 N2 C10 O11 4.8(3) . . . . ? C1 N2 C10 O22 -176.7(5) . . . . ? C10 N2 C1 C9 -125.8(4) . . . . ? C10 N2 C1 C8 116.2(4) . . . . ? C3 N2 C10 O11 178.8(4) . . . . ? C3 N2 C10 O22 -2.6(3) . . . . ? C10 N2 C3 C4 134.0(4) . . . . ? C3 N2 C1 C9 59.9(3) . . . . ? C1 N2 C3 C4 -51.5(3) . . . . ? C3 N2 C1 C8 -58.1(3) . . . . ? C18 C13 C12 O11 -58.2(3) . . . . ? C18 C13 C12 C17 -177.4(4) . . . . ? C12 C13 C18 C19 174.7(4) . . . . ? C12 C13 C18 C20 -59.7(4) . . . . ? C14 C13 C12 O11 174.3(3) . . . . ? C14 C13 C12 C17 55.1(3) . . . . ? C12 C13 C14 C15 -55.2(3) . . . . ? C18 C13 C14 C15 178.3(4) . . . . ? C14 C13 C18 C19 -61.2(3) . . . . ? C14 C13 C18 C20 64.4(4) . . . . ? O11 C12 C17 C16 -174.9(4) . . . . ? C13 C12 C17 C16 -56.2(3) . . . . ? C12 C17 C16 C15 53.1(3) . . . . ? C12 C17 C16 C21 179.4(4) . . . . ? C5 C9 C1 N2 -62.7(3) . . . . ? C1 C9 C5 C4 58.9(3) . . . . ? C5 C9 C1 C8 56.0(3) . . . . ? C1 C9 C5 C6 -64.7(3) . . . . ? C5 C4 C3 N2 48.2(3) . . . . ? C3 C4 C5 C9 -53.7(4) . . . . ? C3 C4 C5 C6 66.9(4) . . . . ? C17 C16 C15 C14 -55.2(3) . . . . ? C21 C16 C15 C14 -179.1(4) . . . . ? C16 C15 C14 C13 58.1(3) . . . . ? C9 C5 C6 C7 39.5(3) . . . . ? C4 C5 C6 C7 -80.7(4) . . . . ? N2 C1 C8 Br1 -82.2(3) . . . . ? N2 C1 C8 C7 94.0(4) . . . . ? C9 C1 C8 Br1 159.5(3) . . . . ? C9 C1 C8 C7 -24.2(3) . . . . ? Br1 C8 C7 C6 175.2(5) . . . . ? C1 C8 C7 C6 -0.7(3) . . . . ? C5 C6 C7 C8 -7.0(4) . . . . ? _geom_special_details ; All standard uncertainties (except dihedral angles between l.s. planes) are estimated using the full covariance matrix. The standard uncertainties in cell dimensions are are used in calculating the standard uncertainties of bond distances, angles and torsion angles. Angles between l.s. planes have standard uncertainties calculated from atomic positional standard uncertainties; the errors in cell dimensions are not used in this case. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C8 1.905(3) . . ? O11 C10 1.349(3) . . ? O11 C12 1.468(3) . . ? O22 C10 1.203(3) . . ? N2 C10 1.371(3) . . ? N2 C1 1.461(4) . . ? N2 C3 1.474(4) . . ? C13 C12 1.517(4) . . ? C13 C18 1.547(4) . . ? C13 C14 1.546(4) . . ? C12 C17 1.509(4) . . ? C17 C16 1.529(4) . . ? C18 C19 1.532(5) . . ? C18 C20 1.509(5) . . ? C9 C5 1.524(5) . . ? C9 C1 1.540(4) . . ? C4 C5 1.525(4) . . ? C4 C3 1.504(5) . . ? C16 C15 1.502(4) . . ? C16 C21 1.519(5) . . ? C15 C14 1.490(5) . . ? C5 C6 1.524(5) . . ? C1 C8 1.495(4) . . ? C8 C7 1.300(4) . . ? C6 C7 1.499(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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 O11 C12 115.6(2) . . . ? C10 N2 C1 124.7(3) . . . ? C10 N2 C3 119.9(3) . . . ? C1 N2 C3 115.2(3) . . . ? C12 C13 C18 112.8(3) . . . ? C12 C13 C14 108.0(3) . . . ? C18 C13 C14 114.4(3) . . . ? O11 C10 O22 124.9(3) . . . ? O11 C10 N2 110.9(3) . . . ? O22 C10 N2 124.2(3) . . . ? O11 C12 C13 107.3(2) . . . ? O11 C12 C17 108.2(3) . . . ? C13 C12 C17 113.0(3) . . . ? C12 C17 C16 112.5(3) . . . ? C13 C18 C19 110.8(3) . . . ? C13 C18 C20 114.1(3) . . . ? C19 C18 C20 110.7(3) . . . ? C5 C9 C1 108.4(3) . . . ? C5 C4 C3 115.6(4) . . . ? C17 C16 C15 108.4(3) . . . ? C17 C16 C21 110.5(3) . . . ? C15 C16 C21 114.6(3) . . . ? C16 C15 C14 114.2(3) . . . ? C9 C5 C4 108.0(4) . . . ? C9 C5 C6 108.7(3) . . . ? C4 C5 C6 113.5(4) . . . ? N2 C1 C9 108.6(3) . . . ? N2 C1 C8 109.3(3) . . . ? C9 C1 C8 108.3(3) . . . ? C13 C14 C15 111.2(3) . . . ? Br1 C8 C1 114.2(3) . . . ? Br1 C8 C7 120.8(3) . . . ? C1 C8 C7 124.9(3) . . . ? N2 C3 C4 109.7(3) . . . ? C5 C6 C7 114.5(3) . . . ? C8 C7 C6 121.7(3) . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Br1 C4 3.516(4) 1_555 1_655 ? Br1 C5 3.797(4) 1_555 1_655 ? Br1 C3 3.795(3) 1_555 2_747 ? O22 C7 3.511(4) 1_555 2_757 ? O22 H7 2.611(2) 1_555 2_757 ? C10 C7 3.857(4) 1_555 2_757 ? C10 H7 3.125(3) 1_555 2_757 ? C17 C19 3.901(4) 1_555 1_455 ? C9 C15 3.967(4) 1_555 2_746 ? C9 C14 3.731(4) 1_555 2_746 ? C9 C21 3.947(5) 1_555 2_646 ? C15 C1 3.860(4) 1_555 2_756 ? C15 C7 3.832(4) 1_555 1_554 ? C15 H1 3.162(3) 1_555 2_756 ? C1 C14 3.965(4) 1_555 2_746 ? C1 H15A 3.170(3) 1_555 2_746 ? C8 C3 3.975(4) 1_555 2_747 ? C3 C7 3.764(4) 1_555 2_757 ? C21 H6B 3.137(4) 1_555 1_554 ? Br1 C4 3.516(4) 1_555 1_655 ? Br1 C5 3.797(4) 1_555 1_655 ? Br1 C3 3.795(3) 1_555 2_747 ? O22 C7 3.511(4) 1_555 2_757 ? O22 H7 2.611(2) 1_555 2_757 ? C10 C7 3.857(4) 1_555 2_757 ? C10 H7 3.125(3) 1_555 2_757 ? C17 C19 3.901(4) 1_555 1_455 ? C9 C15 3.967(4) 1_555 2_746 ? C9 C14 3.731(4) 1_555 2_746 ? C9 C21 3.947(5) 1_555 2_646 ? C15 C1 3.860(4) 1_555 2_756 ? C15 C7 3.832(4) 1_555 1_554 ? C15 H1 3.162(3) 1_555 2_756 ? C1 C14 3.965(4) 1_555 2_746 ? C1 H15A 3.170(3) 1_555 2_746 ? C8 C3 3.975(4) 1_555 2_747 ? C3 C7 3.764(4) 1_555 2_757 ? C21 H6B 3.137(4) 1_555 1_554 ? #=================================================== _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Waasmaier, D. & Kirfel, A. (1995). Acta Cryst. A51, 416-431. Coppens, P. (1970). In Crystallographic Computing, edited by F.R. Ahmed, S.R.Hall & C.P.Huber, pp 255-270. Copenhagen: Munksgaard. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. ; data_mgb60_Cu #------------------------------------------------------------------------------ _audit_creation_date '2000-03-08' _audit_creation_method 'by teXsan v1.8' _audit_update_record ; Original title was 5-jeh-44g_copper_radiation 2000-03-08 cif compiled by acw 2000-03-08 passes checkcif with alerts ; #------------------------------------------------------------------------------ _publ_requested_journal ' test ' _publ_requested_category ' CHOOSE FI FM FO CI CM CO or AD' _publ_contact_author_name ' Anthony C. Willis ' _publ_contact_author_address ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name 'Alison J. Edwards, ajed@rsc.anu.edu.au' _publ_contact_author_phone ' 61 2 6249 4109 ' _publ_contact_author_fax ' 61 2 6249 0750 ' loop_ _publ_author_name _publ_author_footnote _publ_author_address ' FIRST AUTHORS NAME ' ; FIRST AUTHORS FOOTNOTES ; ; FIRST AUTHORS ADDRESS ; _publ_section_title ; mgb60_Cu ; _publ_section_title_footnote ' ENTER ANY FOOTNOTES TO TITLE ' _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_exptl_refinement ; ENTER EXPERIMENTAL SECTION ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. de Meulenaer, J. & Tompa, H. (1965), Acta Cryst. 19, 1014. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1994) ; _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #------------------------------------------------------------------------------ _cell_length_a 9.591(2) _cell_length_b 12.8947(9) _cell_length_c 14.871(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1839.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 193.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 52.6 _cell_measurement_theta_max 54.4 #------------------------------------------------------------------------------ _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_Int_Tables_number 19 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x, -y,1/2+z' '1/2+x,1/2-y, -z' ' -x,1/2+y,1/2-z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'plate' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.14 _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 390.32 _chemical_formula_analytical ? _chemical_formula_sum 'C20 H24 Br N O2 ' _chemical_formula_moiety 'C20 H24 Br N O2 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 808.00 _exptl_absorpt_coefficient_mu 3.138 # units are mm-1 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; analytical (de Meulenaer & Tompa, 1965) ; _exptl_absorpt_correction_T_max 0.661 _exptl_absorpt_correction_T_min 0.394 _exptl_special_details ; The scan width was (1.20+0.30tan\q)\% with an \w scan speed of 16\% per minute (up to 5 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. Data can only be collected to 2theta 120 deg on a AFC6R diffractometer when the evacuated beam tunnel in used. ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 193.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type 'Rigaku AFC6R' _diffrn_measurement_device_details ; Rigaku AFC6R diffractometer with extended arm and evacuated collimator and beam tunnel. Data cannot be collected beyond \y 60 deg in this configuration. ; _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -2.88 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? ? ? ? ? ? ? _diffrn_reflns_number 5862 _reflns_number_total 2738 _reflns_number_gt 2682 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.03673 _diffrn_reflns_av_sigmaI/netI 0.020 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _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 2.97 _diffrn_reflns_theta_max 60.05 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.02782 _diffrn_orient_matrix_UB_12 0.06324 _diffrn_orient_matrix_UB_13 0.03453 _diffrn_orient_matrix_UB_21 -0.04755 _diffrn_orient_matrix_UB_22 -0.04469 _diffrn_orient_matrix_UB_23 0.04560 _diffrn_orient_matrix_UB_31 0.08852 _diffrn_orient_matrix_UB_32 -0.00413 _diffrn_orient_matrix_UB_33 0.03535 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 80 0.017 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 96 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; Br 0 4 -0.767 1.283 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; N 0 4 0.029 0.018 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 8 0.047 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom Br(1) 0.60228(2) 0.50955(1) 0.43078(1) 0.04901(6) 1.000 . Uani d ? O(10) 0.4454(1) 0.30398(8) 0.31321(8) 0.0337(3) 1.000 . Uani d ? O(23) 0.4592(1) 0.13023(9) 0.33957(8) 0.0409(3) 1.000 . Uani d ? N(6) 0.4260(1) 0.2457(1) 0.45223(9) 0.0318(4) 1.000 . Uani d ? C(1) 0.4242(2) 0.2416(2) 0.6107(1) 0.0382(5) 1.000 . Uani d ? C(2) 0.5634(2) 0.2886(1) 0.6409(1) 0.0398(5) 1.000 . Uani d ? C(3) 0.6140(2) 0.3733(1) 0.5798(1) 0.0367(4) 1.000 . Uani d ? C(4) 0.5402(2) 0.4017(1) 0.5093(1) 0.0334(4) 1.000 . Uani d ? C(5) 0.4031(2) 0.3515(1) 0.4866(1) 0.0317(4) 1.000 . Uani d ? C(7) 0.4413(2) 0.1714(1) 0.5272(1) 0.0359(5) 1.000 . Uani d ? C(8) 0.3283(2) 0.3273(2) 0.5752(1) 0.0395(5) 1.000 . Uani d ? C(9) 0.4453(2) 0.2188(1) 0.3662(1) 0.0302(4) 1.000 . Uani d ? C(11) 0.4635(2) 0.2898(1) 0.2176(1) 0.0349(4) 1.000 . Uani d ? C(12) 0.4090(2) 0.3897(1) 0.1740(1) 0.0379(4) 1.000 . Uani d ? C(13) 0.4316(3) 0.3821(2) 0.0721(1) 0.0564(6) 1.000 . Uani d ? C(14) 0.5823(3) 0.3646(2) 0.0492(1) 0.0617(6) 1.000 . Uani d ? C(15) 0.6384(3) 0.2684(2) 0.0945(2) 0.0603(7) 1.000 . Uani d ? C(16) 0.6151(2) 0.2719(2) 0.1959(1) 0.0474(5) 1.000 . Uani d ? C(17) 0.2615(2) 0.4162(1) 0.2016(1) 0.0401(5) 1.000 . Uani d ? C(18) 0.2387(2) 0.4834(2) 0.2724(1) 0.0471(5) 1.000 . Uani d ? C(19) 0.1058(2) 0.5101(2) 0.3000(2) 0.0610(6) 1.000 . Uani d ? C(20) -0.0081(3) 0.4709(2) 0.2558(2) 0.0695(7) 1.000 . Uani d ? C(21) 0.0112(2) 0.4042(2) 0.1856(2) 0.0655(7) 1.000 . Uani d ? C(22) 0.1447(2) 0.3758(2) 0.1580(1) 0.0533(6) 1.000 . Uani d ? H(1) 0.3810 0.2048 0.6586 0.046 1.000 . Uiso c ? H(2) 0.5520 0.3164 0.6996 0.048 1.000 . Uiso c ? H(3) 0.6315 0.2351 0.6423 0.048 1.000 . Uiso c ? H(4) 0.7002 0.4068 0.5922 0.044 1.000 . Uiso c ? H(5) 0.3481 0.3925 0.4472 0.038 1.000 . Uiso c ? H(6) 0.3709 0.1197 0.5252 0.043 1.000 . Uiso c ? H(7) 0.5304 0.1394 0.5264 0.043 1.000 . Uiso c ? H(8) 0.3263 0.3857 0.6141 0.047 1.000 . Uiso c ? H(9) 0.2360 0.3031 0.5655 0.047 1.000 . Uiso c ? H(10) 0.4097 0.2324 0.1978 0.042 1.000 . Uiso c ? H(11) 0.4667 0.4445 0.1949 0.045 1.000 . Uiso c ? H(12) 0.4014 0.4449 0.0449 0.068 1.000 . Uiso c ? H(13) 0.3781 0.3259 0.0494 0.068 1.000 . Uiso c ? H(14) 0.5911 0.3570 -0.0141 0.074 1.000 . Uiso c ? H(15) 0.6351 0.4229 0.0684 0.074 1.000 . Uiso c ? H(16) 0.5923 0.2094 0.0706 0.072 1.000 . Uiso c ? H(17) 0.7356 0.2633 0.0829 0.072 1.000 . Uiso c ? H(18) 0.6437 0.2078 0.2215 0.057 1.000 . Uiso c ? H(19) 0.6690 0.3266 0.2209 0.057 1.000 . Uiso c ? H(20) 0.3166 0.5122 0.3030 0.057 1.000 . Uiso c ? H(21) 0.0934 0.5555 0.3496 0.073 1.000 . Uiso c ? H(22) -0.0996 0.4900 0.2738 0.083 1.000 . Uiso c ? H(23) -0.0675 0.3766 0.1551 0.079 1.000 . Uiso c ? H(24) 0.1562 0.3288 0.1094 0.064 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br(1) 0.0501(1) 0.0390(1) 0.0580(1) -0.00694(9) -0.00882(9) 0.01163(9) O(10) 0.0471(7) 0.0278(6) 0.0262(5) 0.0010(5) 0.0003(5) 0.0002(4) O(23) 0.0518(8) 0.0284(6) 0.0425(7) 0.0010(6) 0.0059(6) -0.0016(5) N(6) 0.0370(8) 0.0288(7) 0.0297(6) 0.0015(6) -0.0007(6) 0.0031(5) C(1) 0.037(1) 0.047(1) 0.0304(9) 0.0053(8) 0.0042(8) 0.0084(7) C(2) 0.042(1) 0.046(1) 0.0309(9) 0.0124(8) -0.0058(8) -0.0005(7) C(3) 0.0345(9) 0.0381(9) 0.0376(9) 0.0063(7) -0.0057(8) -0.0064(7) C(4) 0.0355(9) 0.0305(8) 0.0340(8) 0.0039(7) 0.0013(7) -0.0015(6) C(5) 0.0316(8) 0.0320(8) 0.0316(8) 0.0079(8) -0.0016(7) -0.0003(6) C(7) 0.040(1) 0.0319(9) 0.0362(9) -0.0016(8) -0.0002(8) 0.0081(6) C(8) 0.0315(9) 0.051(1) 0.036(1) 0.0099(8) 0.0033(8) 0.0005(8) C(9) 0.0269(8) 0.0300(8) 0.0337(8) -0.0008(7) -0.0008(7) 0.0010(6) C(11) 0.0443(9) 0.0325(8) 0.0281(8) -0.0087(8) 0.0050(8) -0.0044(7) C(12) 0.0468(9) 0.0360(9) 0.0309(8) -0.0112(9) -0.0004(8) 0.0036(7) C(13) 0.073(1) 0.064(1) 0.0319(9) -0.019(1) 0.005(1) 0.0084(9) C(14) 0.076(1) 0.069(1) 0.041(1) -0.026(1) 0.022(1) -0.0026(9) C(15) 0.064(2) 0.062(1) 0.055(1) -0.019(1) 0.025(1) -0.0181(9) C(16) 0.047(1) 0.045(1) 0.050(1) -0.002(1) 0.012(1) -0.0060(9) C(17) 0.046(1) 0.042(1) 0.0329(8) -0.0038(8) -0.0032(8) 0.0164(7) C(18) 0.058(1) 0.043(1) 0.0407(9) 0.004(1) -0.0017(9) 0.0134(8) C(19) 0.069(1) 0.055(1) 0.060(1) 0.017(1) 0.014(1) 0.021(1) C(20) 0.056(1) 0.069(2) 0.084(2) 0.012(1) 0.015(1) 0.040(1) C(21) 0.045(1) 0.075(2) 0.077(1) -0.011(1) -0.012(1) 0.038(1) C(22) 0.056(1) 0.059(1) 0.045(1) -0.016(1) -0.0075(9) 0.017(1) #------------------------------------------------------------------------------ _refine_special_details ; Hydrogen atoms were included at geometrically determined positions which were periodically recalculated but were not refined. ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'w = 1/[\s^2^(Fo) + 0.00022|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ; Absolute configuration by refinement of Flack parameter ; _refine_ls_abs_structure_Flack -.05(5) _refine_ls_number_reflns 2682 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0205 _refine_ls_R_factor_gt 0.0198 _refine_ls_wR_factor_all 0.0266 _refine_ls_wR_factor_ref 0.0264 _refine_ls_goodness_of_fit_all 1.163 _refine_ls_goodness_of_fit_ref 1.166 _refine_ls_shift/su_max 0.0130 _refine_ls_shift/su_mean 0.2030 _refine_diff_density_min -0.38 _refine_diff_density_max 0.20 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br(1) C(4) 1.912(2) . . yes O(10) C(9) 1.352(2) . . yes O(10) C(11) 1.444(2) . . yes O(23) C(9) 1.216(2) . . yes N(6) C(5) 1.473(2) . . yes N(6) C(7) 1.477(2) . . yes N(6) C(9) 1.338(2) . . yes C(1) C(2) 1.534(3) . . yes C(1) C(7) 1.544(3) . . yes C(1) C(8) 1.532(3) . . yes C(1) H(1) 0.95 . . no C(2) C(3) 1.502(3) . . yes C(2) H(2) 0.95 . . no C(2) H(3) 0.95 . . no C(3) C(4) 1.317(3) . . yes C(3) H(4) 0.95 . . no C(4) C(5) 1.504(3) . . yes C(5) C(8) 1.531(3) . . yes C(5) H(5) 0.95 . . no C(7) H(6) 0.95 . . no C(7) H(7) 0.95 . . no C(8) H(8) 0.95 . . no C(8) H(9) 0.95 . . no C(11) C(12) 1.533(3) . . yes C(11) C(16) 1.507(3) . . yes C(11) H(10) 0.95 . . no C(12) C(13) 1.534(3) . . yes C(12) C(17) 1.512(3) . . yes C(12) H(11) 0.95 . . no C(13) C(14) 1.503(4) . . yes C(13) H(12) 0.95 . . no C(13) H(13) 0.95 . . no C(14) C(15) 1.510(4) . . yes C(14) H(14) 0.95 . . no C(14) H(15) 0.95 . . no C(15) C(16) 1.526(3) . . yes C(15) H(16) 0.95 . . no C(15) H(17) 0.95 . . no C(16) H(18) 0.95 . . no C(16) H(19) 0.95 . . no C(17) C(18) 1.382(3) . . yes C(17) C(22) 1.395(3) . . yes C(18) C(19) 1.383(3) . . yes C(18) H(20) 0.95 . . no C(19) C(20) 1.372(4) . . yes C(19) H(21) 0.95 . . no C(20) C(21) 1.365(4) . . yes C(20) H(22) 0.95 . . no C(21) C(22) 1.393(4) . . yes C(21) H(23) 0.95 . . no C(22) H(24) 0.95 . . no #------------------------------------------------------------------------------ loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(9) O(10) C(11) 118.1(1) . . . yes C(5) N(6) C(7) 110.6(1) . . . yes C(5) N(6) C(9) 126.4(1) . . . yes C(7) N(6) C(9) 122.7(2) . . . yes C(2) C(1) C(7) 112.0(2) . . . yes C(2) C(1) C(8) 109.7(2) . . . yes C(2) C(1) H(1) 110.9 . . . no C(7) C(1) C(8) 102.1(2) . . . yes C(7) C(1) H(1) 110.9 . . . no C(8) C(1) H(1) 110.9 . . . no C(1) C(2) C(3) 113.1(2) . . . yes C(1) C(2) H(2) 108.6 . . . no C(1) C(2) H(3) 108.6 . . . no C(3) C(2) H(2) 108.6 . . . no C(3) C(2) H(3) 108.6 . . . no H(2) C(2) H(3) 109.5 . . . no C(2) C(3) C(4) 120.6(2) . . . yes C(2) C(3) H(4) 119.7 . . . no C(4) C(3) H(4) 119.7 . . . no Br(1) C(4) C(3) 121.4(2) . . . yes Br(1) C(4) C(5) 116.6(1) . . . yes C(3) C(4) C(5) 122.0(2) . . . yes N(6) C(5) C(4) 110.2(1) . . . yes N(6) C(5) C(8) 100.4(1) . . . yes N(6) C(5) H(5) 112.6 . . . no C(4) C(5) C(8) 107.7(2) . . . yes C(4) C(5) H(5) 112.6 . . . no C(8) C(5) H(5) 112.6 . . . no N(6) C(7) C(1) 102.5(1) . . . yes N(6) C(7) H(6) 111.2 . . . no N(6) C(7) H(7) 111.2 . . . no C(1) C(7) H(6) 111.2 . . . no C(1) C(7) H(7) 111.2 . . . no H(6) C(7) H(7) 109.5 . . . no C(1) C(8) C(5) 99.4(1) . . . yes C(1) C(8) H(8) 111.9 . . . no C(1) C(8) H(9) 111.9 . . . no C(5) C(8) H(8) 111.9 . . . no C(5) C(8) H(9) 111.9 . . . no H(8) C(8) H(9) 109.5 . . . no O(10) C(9) O(23) 124.9(2) . . . yes O(10) C(9) N(6) 110.3(1) . . . yes O(23) C(9) N(6) 124.8(2) . . . yes O(10) C(11) C(12) 105.6(2) . . . yes O(10) C(11) C(16) 110.2(2) . . . yes O(10) C(11) H(10) 109.8 . . . no C(12) C(11) C(16) 111.6(2) . . . yes C(12) C(11) H(10) 109.8 . . . no C(16) C(11) H(10) 109.8 . . . no C(11) C(12) C(13) 108.4(2) . . . yes C(11) C(12) C(17) 113.2(2) . . . yes C(11) C(12) H(11) 106.7 . . . no C(13) C(12) C(17) 114.5(2) . . . yes C(13) C(12) H(11) 106.7 . . . no C(17) C(12) H(11) 106.7 . . . no C(12) C(13) C(14) 111.7(2) . . . yes C(12) C(13) H(12) 108.9 . . . no C(12) C(13) H(13) 108.9 . . . no C(14) C(13) H(12) 108.9 . . . no C(14) C(13) H(13) 108.9 . . . no H(12) C(13) H(13) 109.5 . . . no C(13) C(14) C(15) 111.4(2) . . . yes C(13) C(14) H(14) 109.0 . . . no C(13) C(14) H(15) 109.0 . . . no C(15) C(14) H(14) 109.0 . . . no C(15) C(14) H(15) 109.0 . . . no H(14) C(14) H(15) 109.5 . . . no C(14) C(15) C(16) 111.4(2) . . . yes C(14) C(15) H(16) 109.0 . . . no C(14) C(15) H(17) 109.0 . . . no C(16) C(15) H(16) 109.0 . . . no C(16) C(15) H(17) 109.0 . . . no H(16) C(15) H(17) 109.5 . . . no C(11) C(16) C(15) 110.9(2) . . . yes C(11) C(16) H(18) 109.1 . . . no C(11) C(16) H(19) 109.1 . . . no C(15) C(16) H(18) 109.1 . . . no C(15) C(16) H(19) 109.1 . . . no H(18) C(16) H(19) 109.5 . . . no C(12) C(17) C(18) 119.8(2) . . . yes C(12) C(17) C(22) 122.8(2) . . . yes C(18) C(17) C(22) 117.5(2) . . . yes C(17) C(18) C(19) 121.9(2) . . . yes C(17) C(18) H(20) 119.1 . . . no C(19) C(18) H(20) 119.1 . . . no C(18) C(19) C(20) 120.1(2) . . . yes C(18) C(19) H(21) 120.0 . . . no C(20) C(19) H(21) 120.0 . . . no C(19) C(20) C(21) 119.3(2) . . . yes C(19) C(20) H(22) 120.3 . . . no C(21) C(20) H(22) 120.3 . . . no C(20) C(21) C(22) 121.0(3) . . . yes C(20) C(21) H(23) 119.5 . . . no C(22) C(21) H(23) 119.5 . . . no C(17) C(22) C(21) 120.2(3) . . . yes C(17) C(22) H(24) 119.9 . . . no C(21) C(22) H(24) 119.9 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(23) C(12) 3.356(2) . 4_645 no O(23) C(3) 3.521(2) . 3_456 no N(6) C(3) 3.396(2) . 3_456 no C(1) C(20) 3.445(3) . 3_556 no C(2) C(20) 3.580(3) . 2_565 no C(3) C(20) 3.451(3) . 2_565 no C(3) C(9) 3.486(3) . 3_556 no C(3) C(21) 3.486(3) . 2_565 no C(3) C(7) 3.566(3) . 3_556 no #------------------------------------------------------------------------------ loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag Br(1) C(4) C(3) C(2) . . . . 179.8(1) no Br(1) C(4) C(5) N(6) . . . . 108.1(1) no Br(1) C(4) C(5) C(8) . . . . -143.3(1) no O(10) C(9) N(6) C(5) . . . . 1.9(3) no O(10) C(9) N(6) C(7) . . . . -170.9(2) no O(10) C(11) C(12) C(13) . . . . 177.3(2) no O(10) C(11) C(12) C(17) . . . . -54.5(2) no O(10) C(11) C(16) C(15) . . . . -173.9(2) no O(23) C(9) O(10) C(11) . . . . -0.1(3) no O(23) C(9) N(6) C(5) . . . . -177.3(2) no O(23) C(9) N(6) C(7) . . . . 9.9(3) no N(6) C(5) C(4) C(3) . . . . -72.2(2) no N(6) C(5) C(8) C(1) . . . . 46.6(2) no N(6) C(7) C(1) C(2) . . . . -88.1(2) no N(6) C(7) C(1) C(8) . . . . 29.2(2) no N(6) C(9) O(10) C(11) . . . . -179.3(2) no C(1) C(2) C(3) C(4) . . . . 1.0(3) no C(1) C(7) N(6) C(5) . . . . 0.5(2) no C(1) C(7) N(6) C(9) . . . . 174.3(2) no C(1) C(8) C(5) C(4) . . . . -68.8(2) no C(2) C(1) C(8) C(5) . . . . 71.7(2) no C(2) C(3) C(4) C(5) . . . . 0.1(3) no C(3) C(2) C(1) C(7) . . . . 73.6(2) no C(3) C(2) C(1) C(8) . . . . -39.0(2) no C(3) C(4) C(5) C(8) . . . . 36.4(2) no C(4) C(5) N(6) C(7) . . . . 83.5(2) no C(4) C(5) N(6) C(9) . . . . -90.0(2) no C(5) C(8) C(1) C(7) . . . . -47.2(2) no C(7) N(6) C(5) C(8) . . . . -29.9(2) no C(8) C(5) N(6) C(9) . . . . 156.6(2) no C(9) O(10) C(11) C(12) . . . . 160.7(2) no C(9) O(10) C(11) C(16) . . . . -78.7(2) no C(11) C(12) C(13) C(14) . . . . -57.4(2) no C(11) C(12) C(17) C(18) . . . . 94.6(2) no C(11) C(12) C(17) C(22) . . . . -85.8(2) no C(11) C(16) C(15) C(14) . . . . 54.5(3) no C(12) C(11) C(16) C(15) . . . . -56.9(2) no C(12) C(13) C(14) C(15) . . . . 56.9(3) no C(12) C(17) C(18) C(19) . . . . 179.9(2) no C(12) C(17) C(22) C(21) . . . . -179.1(2) no C(13) C(12) C(11) C(16) . . . . 57.6(2) no C(13) C(12) C(17) C(18) . . . . -140.5(2) no C(13) C(12) C(17) C(22) . . . . 39.2(3) no C(13) C(14) C(15) C(16) . . . . -54.5(3) no C(14) C(13) C(12) C(17) . . . . 175.2(2) no C(16) C(11) C(12) C(17) . . . . -174.3(2) no C(17) C(18) C(19) C(20) . . . . -1.2(3) no C(17) C(22) C(21) C(20) . . . . -0.5(4) no C(18) C(17) C(22) C(21) . . . . 0.6(3) no C(18) C(19) C(20) C(21) . . . . 1.2(4) no C(19) C(18) C(17) C(22) . . . . 0.3(3) no C(19) C(20) C(21) C(22) . . . . -0.4(4) no #------------------------------------------------------------------------------ #===END data_MGB46 #------------------------------------------------------------------------------ _audit_creation_date '2000-03-09' _audit_creation_method 'by teXsan v1.8' _audit_update_record ; 1999 data collection and refinement by dcrh 2000-03-09 cif compiled by acwillis 2000-03-09 passes checkcif with alerts ; #------------------------------------------------------------------------------ _publ_requested_journal ' test ' _publ_requested_category ' CHOOSE FI FM FO CI CM CO or AD' _publ_contact_author_name ' David C. R. Hockless ' _publ_contact_author_address ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ' Dr Alison Edwards' _publ_contact_author_phone ' 61 2 6249 4109 ' _publ_contact_author_fax ' 61 2 6249 0750 ' _publ_contact_author_email ' ajed@rsc.anu.edu.au ' loop_ _publ_author_name _publ_author_footnote _publ_author_address ' FIRST AUTHORS NAME ' ; FIRST AUTHORS FOOTNOTES ; ; FIRST AUTHORS ADDRESS ; _publ_section_title ; mgb64 ; _publ_section_title_footnote ' ENTER ANY FOOTNOTES TO TITLE ' _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_exptl_refinement ; ENTER EXPERIMENTAL SECTION ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1994) ; _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #------------------------------------------------------------------------------ _cell_length_a 7.080(3) _cell_length_b 9.637(1) _cell_length_c 29.064(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1982.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 193.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 47.7 _cell_measurement_theta_max 49.9 #------------------------------------------------------------------------------ _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_Int_Tables_number 19 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x, -y,1/2+z' '1/2+x,1/2-y, -z' ' -x,1/2+y,1/2-z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 451.24 _chemical_formula_analytical ? _chemical_formula_sum 'C18 H29 Br2 N O2 ' _chemical_formula_moiety 'C18 H29 Br2 N O2 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 920.00 _exptl_absorpt_coefficient_mu 5.294 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max .853 _exptl_absorpt_correction_T_min .666 _exptl_special_details ; The scan width was (1.30+0.30tan\q)\% with an \w scan speed of 16\% per minute (up to 5 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 193.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type 'Rigaku AFC6R' _diffrn_measurement_device_details ; Rigaku AFC6R diffractometer with extended arm and evacuated collimator and beam tunnel. Data cannot be collected beyond \y 60 deg in this configuration. ; _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -4.76 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 1 1 0 4 0 0 0 8 _diffrn_reflns_number 1730 _reflns_number_total 1730 _reflns_number_gt 1605 _reflns_threshold_expression I>3.00\s(I) _diffrn_reflns_av_R_equivalents 0.00000 _diffrn_reflns_av_sigmaI/netI 0.020 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 59.96 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.07276 _diffrn_orient_matrix_UB_12 0.05433 _diffrn_orient_matrix_UB_13 0.02335 _diffrn_orient_matrix_UB_21 0.11765 _diffrn_orient_matrix_UB_22 0.01234 _diffrn_orient_matrix_UB_23 0.01860 _diffrn_orient_matrix_UB_31 0.02857 _diffrn_orient_matrix_UB_32 0.08754 _diffrn_orient_matrix_UB_33 -0.01711 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 72 0.017 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 116 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; Br 0 8 -0.767 1.283 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; N 0 4 0.029 0.018 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 8 0.047 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom Br(1) 0.5301(1) 0.77159(8) 0.45959(2) 0.0685(2) 1.000 . Uani d ? Br(2) 0.6195(1) 1.05310(8) 0.40897(3) 0.0716(3) 1.000 . Uani d ? O(1) 1.0406(6) 0.7766(4) 0.2275(1) 0.043(1) 1.000 . Uani d ? O(2) 0.9642(6) 0.9772(3) 0.1910(1) 0.038(1) 1.000 . Uani d ? N(1) 1.0664(7) 0.9873(5) 0.2622(1) 0.038(1) 1.000 . Uani d ? C(1) 0.741(1) 0.7764(6) 0.3746(2) 0.049(2) 1.000 . Uani d ? C(1') 0.8925(9) 0.9038(5) 0.1505(2) 0.039(2) 1.000 . Uani d ? C(2) 0.804(1) 0.8442(7) 0.3309(2) 0.054(2) 1.000 . Uani d ? C(2') 0.7035(8) 0.9699(6) 0.1378(2) 0.042(2) 1.000 . Uani d ? C(3) 0.971(1) 0.9436(6) 0.3421(2) 0.046(2) 1.000 . Uani d ? C(3') 0.6378(9) 0.9110(7) 0.0920(2) 0.055(2) 1.000 . Uani d ? C(4) 1.038(1) 0.8994(7) 0.3912(2) 0.053(2) 1.000 . Uani d ? C(4') 0.784(1) 0.9267(7) 0.0544(2) 0.058(2) 1.000 . Uani d ? C(5) 0.885(1) 0.8125(6) 0.4119(2) 0.051(2) 1.000 . Uani d ? C(5') 0.972(1) 0.8559(6) 0.0670(2) 0.049(2) 1.000 . Uani d ? C(6) 0.692(1) 0.8595(6) 0.4148(2) 0.052(2) 1.000 . Uani d ? C(6') 1.0394(9) 0.9119(5) 0.1137(2) 0.039(2) 1.000 . Uani d ? C(7) 1.1281(9) 0.9381(6) 0.3072(2) 0.045(2) 1.000 . Uani d ? C(7') 0.5450(9) 0.9568(7) 0.1746(2) 0.051(2) 1.000 . Uani d ? C(8') 0.535(1) 0.8113(7) 0.1963(3) 0.064(2) 1.000 . Uani d ? C(9') 0.554(1) 1.0675(8) 0.2119(2) 0.063(2) 1.000 . Uani d ? C(10') 1.120(1) 0.8746(8) 0.0308(2) 0.068(2) 1.000 . Uani d ? C(11') 1.0263(9) 0.9021(6) 0.2272(2) 0.036(2) 1.000 . Uani d ? H(1) 0.6634 0.6733 0.3755 0.098 1.000 . Uiso c ? H(1') 0.8722 0.8092 0.1583 0.046 1.000 . Uiso c ? H(01) 1.0361 1.0959 0.2569 0.098 1.000 . Uiso c ? H(2a) 0.7029 0.8954 0.3179 0.065 1.000 . Uiso c ? H(2') 0.7259 1.0661 0.1333 0.050 1.000 . Uiso c ? H(2b) 0.8450 0.7754 0.3096 0.065 1.000 . Uiso c ? H(3'a) 0.5881 0.8303 0.0971 0.098 1.000 . Uiso c ? H(3'b) 0.5096 0.9345 0.0809 0.098 1.000 . Uiso c ? H(3) 0.9241 1.0359 0.3436 0.055 1.000 . Uiso c ? H(4b) 1.1517 0.8472 0.3891 0.063 1.000 . Uiso c ? H(4'a) 0.8068 1.0227 0.0494 0.070 1.000 . Uiso c ? H(4'b) 0.7368 0.8860 0.0269 0.070 1.000 . Uiso c ? H(4a) 1.0593 0.9793 0.4097 0.063 1.000 . Uiso c ? H(5') 0.9443 0.7677 0.0740 0.098 1.000 . Uiso c ? H(5) 0.9255 0.7466 0.4375 0.098 1.000 . Uiso c ? H(6'b) 1.1549 0.8588 0.1206 0.098 1.000 . Uiso c ? H(6'a) 1.0737 1.0147 0.1083 0.098 1.000 . Uiso c ? H(7a) 1.1624 0.8381 0.3081 0.098 1.000 . Uiso c ? H(7') 0.4133 1.0006 0.1551 0.098 1.000 . Uiso c ? H(7b) 1.2358 0.9745 0.3218 0.098 1.000 . Uiso c ? H(8'b) 0.6454 0.7950 0.2139 0.077 1.000 . Uiso c ? H(8'c) 0.5255 0.7435 0.1726 0.077 1.000 . Uiso c ? H(8'a) 0.4269 0.8056 0.2156 0.077 1.000 . Uiso c ? H(9'b) 0.4461 1.0603 0.2311 0.076 1.000 . Uiso c ? H(9'c) 0.5572 1.1568 0.1980 0.076 1.000 . Uiso c ? H(9'a) 0.6651 1.0545 0.2298 0.076 1.000 . Uiso c ? H(10'b) 1.0651 0.8611 0.0013 0.081 1.000 . Uiso c ? H(10'c) 1.2181 0.8089 0.0353 0.081 1.000 . Uiso c ? H(10'a) 1.1703 0.9658 0.0327 0.081 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br(1) 0.1030(6) 0.0603(4) 0.0423(4) -0.0130(5) 0.0126(4) 0.0035(3) Br(2) 0.1042(7) 0.0435(4) 0.0671(5) 0.0158(5) 0.0229(5) 0.0018(4) O(1) 0.055(2) 0.029(2) 0.045(2) 0.002(2) -0.001(2) 0.004(2) O(2) 0.054(2) 0.026(2) 0.034(2) -0.006(2) -0.006(2) 0.000(2) N(1) 0.044(3) 0.035(2) 0.035(2) -0.004(2) -0.001(2) 0.000(2) C(1) 0.070(4) 0.035(3) 0.041(3) -0.002(4) -0.005(3) 0.003(3) C(1') 0.046(3) 0.030(3) 0.041(3) -0.005(3) -0.007(3) 0.001(2) C(2) 0.057(4) 0.066(4) 0.038(3) -0.008(4) -0.003(3) -0.010(3) C(2') 0.046(3) 0.027(3) 0.053(3) 0.003(3) -0.010(3) 0.001(3) C(3) 0.062(4) 0.044(3) 0.031(3) -0.002(4) -0.007(3) -0.003(2) C(3') 0.045(4) 0.058(4) 0.062(4) -0.009(3) -0.022(4) 0.014(3) C(4) 0.067(4) 0.054(4) 0.037(3) -0.004(4) -0.014(3) -0.003(3) C(4') 0.077(5) 0.047(4) 0.050(4) -0.002(4) -0.027(4) 0.001(3) C(5) 0.074(5) 0.044(3) 0.036(3) 0.006(4) -0.013(3) 0.000(3) C(5') 0.072(4) 0.035(3) 0.042(3) 0.005(3) -0.010(3) -0.001(3) C(6) 0.084(5) 0.038(3) 0.036(3) -0.006(4) 0.002(4) 0.003(3) C(6') 0.046(3) 0.029(3) 0.043(3) -0.003(3) -0.005(3) 0.001(2) C(7) 0.049(4) 0.045(3) 0.042(3) -0.002(3) -0.009(3) 0.000(3) C(7') 0.042(3) 0.043(3) 0.067(4) 0.005(3) -0.002(3) 0.010(3) C(8') 0.053(4) 0.057(4) 0.081(5) -0.007(4) 0.007(4) 0.017(4) C(9') 0.053(4) 0.065(4) 0.071(4) -0.001(4) 0.005(4) -0.004(4) C(10') 0.096(6) 0.064(4) 0.042(4) 0.016(5) -0.008(4) -0.003(3) C(11') 0.037(3) 0.036(3) 0.036(3) 0.001(3) 0.002(3) 0.004(2) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'w = 1/[\s^2^(Fo) + 0.00008|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ; Absolute configuration assigned by comparative refinement. After refinement with coordinates transformed by (-x,-y,-z), R = 0.0392, Rw = 0.0493, GOF = 3.06. ; _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1605 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0360 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_all 0.0416 _refine_ls_wR_factor_ref 0.0412 _refine_ls_goodness_of_fit_all 2.480 _refine_ls_goodness_of_fit_ref 2.562 _refine_ls_shift/su_max 0.0250 _refine_ls_shift/su_mean 0.0006 _refine_diff_density_min -0.38 _refine_diff_density_max 0.52 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br(1) C(6) 1.929(7) . . yes Br(2) C(6) 1.941(6) . . yes O(1) C(11') 1.214(6) . . yes O(2) C(1') 1.462(6) . . yes O(2) C(11') 1.352(6) . . yes N(1) C(7) 1.457(7) . . yes N(1) C(11') 1.337(7) . . yes N(1) H(01) 1.08 . . no C(1) C(2) 1.497(8) . . yes C(1) C(5) 1.528(8) . . yes C(1) C(6) 1.460(8) . . yes C(1) H(1) 1.14 . . no C(1') C(2') 1.527(8) . . yes C(1') C(6') 1.494(8) . . yes C(1') H(1') 0.95 . . no C(2) C(3) 1.555(9) . . yes C(2) H(2a) 0.95 . . no C(2) H(2b) 0.95 . . no C(2') C(3') 1.521(8) . . yes C(2') C(7') 1.554(8) . . yes C(2') H(2') 0.95 . . no C(3) C(4) 1.563(7) . . yes C(3) C(7) 1.507(9) . . yes C(3) H(3) 0.95 . . no C(3') C(4') 1.51(1) . . yes C(3') H(3'a) 0.87 . . no C(3') H(3'b) 0.99 . . no C(4) C(5) 1.494(9) . . yes C(4) H(4b) 0.95 . . no C(4) H(4a) 0.95 . . no C(4') C(5') 1.54(1) . . yes C(4') H(4'a) 0.95 . . no C(4') H(4'b) 0.95 . . no C(5) C(6) 1.45(1) . . yes C(5) H(5) 1.02 . . no C(5') C(6') 1.538(7) . . yes C(5') C(10') 1.49(1) . . yes C(5') H(5') 0.90 . . no C(6') H(6'b) 0.99 . . no C(6') H(6'a) 1.03 . . no C(7) H(7a) 0.99 . . no C(7) H(7b) 0.94 . . no C(7') C(8') 1.540(9) . . yes C(7') C(9') 1.523(9) . . yes C(7') H(7') 1.17 . . no C(8') H(8'b) 0.95 . . no C(8') H(8'c) 0.95 . . no C(8') H(8'a) 0.95 . . no C(9') H(9'b) 0.95 . . no C(9') H(9'c) 0.95 . . no C(9') H(9'a) 0.95 . . no C(10') H(10'b 0.95 . . no C(10') H(10'c 0.95 . . no C(10') H(10'a 0.95 . . no #------------------------------------------------------------------------------ loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(1') O(2) C(11') 118.7(4) . . . yes C(7) N(1) C(11') 123.1(5) . . . yes C(7) N(1) H(01) 120.3 . . . no C(11') N(1) H(01) 116.3 . . . no C(2) C(1) C(5) 107.6(5) . . . yes C(2) C(1) C(6) 120.8(5) . . . yes C(2) C(1) H(1) 123.2 . . . no C(5) C(1) C(6) 57.9(4) . . . yes C(5) C(1) H(1) 120.3 . . . no C(6) C(1) H(1) 110.0 . . . no O(2) C(1') C(2') 107.3(4) . . . yes O(2) C(1') C(6') 108.0(4) . . . yes O(2) C(1') H(1') 109.0 . . . no C(2') C(1') C(6') 114.5(4) . . . yes C(2') C(1') H(1') 109.0 . . . no C(6') C(1') H(1') 109.0 . . . no C(1) C(2) C(3) 108.5(5) . . . yes C(1) C(2) H(2a) 109.7 . . . no C(1) C(2) H(2b) 109.7 . . . no C(3) C(2) H(2a) 109.7 . . . no C(3) C(2) H(2b) 109.7 . . . no H(2a) C(2) H(2b) 109.5 . . . no C(1') C(2') C(3') 109.0(5) . . . yes C(1') C(2') C(7') 115.6(5) . . . yes C(1') C(2') H(2') 107.1 . . . no C(3') C(2') C(7') 110.6(5) . . . yes C(3') C(2') H(2') 107.1 . . . no C(7') C(2') H(2') 107.1 . . . no C(2) C(3) C(4) 104.8(5) . . . yes C(2) C(3) C(7) 113.3(4) . . . yes C(2) C(3) H(3) 108.7 . . . no C(4) C(3) C(7) 112.4(5) . . . yes C(4) C(3) H(3) 108.7 . . . no C(7) C(3) H(3) 108.7 . . . no C(2') C(3') C(4') 112.7(5) . . . yes C(2') C(3') H(3'a) 107.9 . . . no C(2') C(3') H(3'b) 118.7 . . . no C(4') C(3') H(3'a) 119.5 . . . no C(4') C(3') H(3'b) 111.7 . . . no H(3'a) C(3') H(3'b) 83.7 . . . no C(3) C(4) C(5) 107.4(5) . . . yes C(3) C(4) H(4b) 110.0 . . . no C(3) C(4) H(4a) 110.0 . . . no C(5) C(4) H(4b) 110.0 . . . no C(5) C(4) H(4a) 110.0 . . . no H(4b) C(4) H(4a) 109.5 . . . no C(3') C(4') C(5') 112.1(5) . . . yes C(3') C(4') H(4'a) 108.8 . . . no C(3') C(4') H(4'b) 108.8 . . . no C(5') C(4') H(4'a) 108.8 . . . no C(5') C(4') H(4'b) 108.8 . . . no H(4'a) C(4') H(4'b) 109.5 . . . no C(1) C(5) C(4) 109.1(5) . . . yes C(1) C(5) C(6) 58.7(4) . . . yes C(1) C(5) H(5) 124.2 . . . no C(4) C(5) C(6) 122.3(6) . . . yes C(4) C(5) H(5) 116.1 . . . no C(6) C(5) H(5) 114.6 . . . no C(4') C(5') C(6') 108.8(5) . . . yes C(4') C(5') C(10') 112.6(5) . . . yes C(4') C(5') H(5') 106.6 . . . no C(6') C(5') C(10') 111.3(6) . . . yes C(6') C(5') H(5') 101.6 . . . no C(10') C(5') H(5') 115.3 . . . no Br(1) C(6) Br(2) 109.0(4) . . . yes Br(1) C(6) C(1) 116.2(4) . . . yes Br(1) C(6) C(5) 117.7(5) . . . yes Br(2) C(6) C(1) 121.3(4) . . . yes Br(2) C(6) C(5) 123.0(5) . . . yes C(1) C(6) C(5) 63.4(5) . . . yes C(1') C(6') C(5') 113.5(5) . . . yes C(1') C(6') H(6'b) 113.9 . . . no C(1') C(6') H(6'a) 108.9 . . . no C(5') C(6') H(6'b) 104.7 . . . no C(5') C(6') H(6'a) 105.9 . . . no H(6'b) C(6') H(6'a) 109.5 . . . no N(1) C(7) C(3) 111.9(5) . . . yes N(1) C(7) H(7a) 114.4 . . . no N(1) C(7) H(7b) 121.8 . . . no C(3) C(7) H(7a) 101.3 . . . no C(3) C(7) H(7b) 106.2 . . . no H(7a) C(7) H(7b) 98.7 . . . no C(2') C(7') C(8') 112.9(5) . . . yes C(2') C(7') C(9') 113.7(5) . . . yes C(2') C(7') H(7') 102.3 . . . no C(8') C(7') C(9') 110.4(6) . . . yes C(8') C(7') H(7') 119.3 . . . no C(9') C(7') H(7') 97.3 . . . no C(7') C(8') H(8'b) 109.5 . . . no C(7') C(8') H(8'c) 109.5 . . . no C(7') C(8') H(8'a) 109.5 . . . no H(8'b) C(8') H(8'c) 109.5 . . . no H(8'b) C(8') H(8'a) 109.5 . . . no H(8'c) C(8') H(8'a) 109.5 . . . no C(7') C(9') H(9'b) 109.5 . . . no C(7') C(9') H(9'c) 109.5 . . . no C(7') C(9') H(9'a) 109.5 . . . no H(9'b) C(9') H(9'c) 109.5 . . . no H(9'b) C(9') H(9'a) 109.5 . . . no H(9'c) C(9') H(9'a) 109.5 . . . no C(5') C(10') H(10'b 109.5 . . . no C(5') C(10') H(10'c 109.5 . . . no C(5') C(10') H(10'a 109.5 . . . no H(10'b C(10') H(10'c 109.5 . . . no H(10'b C(10') H(10'a 109.5 . . . no H(10'c C(10') H(10'a 109.5 . . . no O(1) C(11') O(2) 124.4(5) . . . yes O(1) C(11') N(1) 126.1(5) . . . yes O(2) C(11') N(1) 109.5(5) . . . yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(1) N(1) 2.905(6) . 4_745 no #------------------------------------------------------------------------------ loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag Br(1) C(6) C(1) C(2) . . . . 158.2(5) no Br(1) C(6) C(1) C(5) . . . . -109.4(6) no Br(1) C(6) C(5) C(1) . . . . 107.2(5) no Br(1) C(6) C(5) C(4) . . . . -158.9(4) no Br(2) C(6) C(1) C(2) . . . . 22(1) no Br(2) C(6) C(1) C(5) . . . . 114.1(6) no Br(2) C(6) C(5) C(1) . . . . -111.6(5) no Br(2) C(6) C(5) C(4) . . . . -17.7(8) no O(1) C(11') O(2) C(1') . . . . 6.0(9) no O(1) C(11') N(1) C(7) . . . . -2(1) no O(2) C(1') C(2') C(3') . . . . 171.8(4) no O(2) C(1') C(2') C(7') . . . . -63.0(6) no O(2) C(1') C(6') C(5') . . . . -172.2(4) no O(2) C(11') N(1) C(7) . . . . 176.9(5) no N(1) C(7) C(3) C(2) . . . . 64.8(7) no N(1) C(7) C(3) C(4) . . . . -176.6(5) no N(1) C(11') O(2) C(1') . . . . -173.4(5) no C(1) C(2) C(3) C(4) . . . . 15.6(7) no C(1) C(2) C(3) C(7) . . . . 138.5(6) no C(1) C(5) C(4) C(3) . . . . 10.9(7) no C(1) C(6) C(5) C(4) . . . . 93.9(6) no C(1') C(2') C(3') C(4') . . . . -54.3(6) no C(1') C(2') C(7') C(8') . . . . -43.2(7) no C(1') C(2') C(7') C(9') . . . . 83.6(6) no C(1') C(6') C(5') C(4') . . . . 51.8(6) no C(1') C(6') C(5') C(10') . . . . 176.4(5) no C(2) C(1) C(5) C(4) . . . . -1.1(7) no C(2) C(1) C(5) C(6) . . . . 115.8(6) no C(2) C(1) C(6) C(5) . . . . -92.4(7) no C(2) C(3) C(4) C(5) . . . . -16.1(6) no C(2') C(1') O(2) C(11') . . . . 131.4(5) no C(2') C(1') C(6') C(5') . . . . -52.8(6) no C(2') C(3') C(4') C(5') . . . . 58.0(7) no C(3) C(2) C(1) C(5) . . . . -9.3(7) no C(3) C(2) C(1) C(6) . . . . 53.3(8) no C(3) C(4) C(5) C(6) . . . . -53.5(7) no C(3) C(7) N(1) C(11') . . . . -102.9(6) no C(3') C(2') C(1') C(6') . . . . 52.0(6) no C(3') C(2') C(7') C(8') . . . . 81.2(7) no C(3') C(2') C(7') C(9') . . . . -152.0(5) no C(3') C(4') C(5') C(6') . . . . -54.3(7) no C(3') C(4') C(5') C(10') . . . . -178.1(5) no C(4) C(5) C(1) C(6) . . . . -116.9(6) no C(4') C(3') C(2') C(7') . . . . 177.6(5) no C(5) C(4) C(3) C(7) . . . . -139.6(5) no C(6') C(1') O(2) C(11') . . . . -104.7(5) no C(6') C(1') C(2') C(7') . . . . 177.2(5) no #------------------------------------------------------------------------------