# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_cheny21 _database_code_depnum_ccdc_archive 'CCDC 812056' #TrackingRef 'CHENY21.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H20 Br N O' _chemical_formula_weight 394.30 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 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.7061(5) _cell_length_b 17.0480(15) _cell_length_c 18.4614(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1795.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 100 _cell_measurement_theta_min 5 _cell_measurement_theta_max 85 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 3.178 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.760 _exptl_absorpt_correction_T_max 0.770 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_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 10032 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0298 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 65.94 _reflns_number_total 2984 _reflns_number_gt 2936 _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^)+(0.0374P)^2^+0.5036P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.004(15) _refine_ls_number_reflns 2984 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0231 _refine_ls_R_factor_gt 0.0228 _refine_ls_wR_factor_ref 0.0640 _refine_ls_wR_factor_gt 0.0637 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 1.00758(4) 0.715336(11) 0.666051(10) 0.02731(9) Uani 1 1 d . . . O1 O 0.4097(2) 0.09888(8) 0.43471(7) 0.0190(3) Uani 1 1 d . . . N1 N 0.8193(3) 0.40603(10) 0.29892(9) 0.0196(4) Uani 1 1 d . . . H1A H 0.8667 0.3603 0.2824 0.024 Uiso 1 1 calc R . . C1 C 0.9437(3) 0.47336(12) 0.28166(10) 0.0181(4) Uani 1 1 d . . . C2 C 1.1094(4) 0.47076(13) 0.22522(11) 0.0218(4) Uani 1 1 d . . . H2A H 1.1306 0.4233 0.1990 0.026 Uiso 1 1 calc R . . C3 C 1.2412(4) 0.53527(14) 0.20724(11) 0.0252(5) Uani 1 1 d . . . H3A H 1.3522 0.5321 0.1690 0.030 Uiso 1 1 calc R . . C4 C 1.2123(4) 0.60523(14) 0.24490(11) 0.0264(5) Uani 1 1 d . . . H4A H 1.3021 0.6502 0.2325 0.032 Uiso 1 1 calc R . . C5 C 1.0503(4) 0.60839(13) 0.30100(11) 0.0245(5) Uani 1 1 d . . . H5A H 1.0312 0.6561 0.3269 0.029 Uiso 1 1 calc R . . C6 C 0.9145(3) 0.54339(12) 0.32040(10) 0.0181(4) Uani 1 1 d . . . C7 C 0.7323(4) 0.54868(12) 0.38055(11) 0.0183(4) Uani 1 1 d . . . H7A H 0.5893 0.5744 0.3602 0.022 Uiso 1 1 calc R . . C8 C 0.8104(4) 0.59560(11) 0.44613(11) 0.0176(4) Uani 1 1 d . . . C9 C 1.0247(4) 0.58031(11) 0.47958(10) 0.0204(4) Uani 1 1 d . . . H9A H 1.1315 0.5448 0.4575 0.025 Uiso 1 1 calc R . . C10 C 1.0849(4) 0.61613(12) 0.54468(10) 0.0202(4) Uani 1 1 d . . . H10A H 1.2309 0.6053 0.5672 0.024 Uiso 1 1 calc R . . C11 C 0.9285(4) 0.66765(11) 0.57581(10) 0.0201(4) Uani 1 1 d . . . C12 C 0.7159(4) 0.68537(12) 0.54382(11) 0.0216(4) Uani 1 1 d . . . H12A H 0.6114 0.7218 0.5656 0.026 Uiso 1 1 calc R . . C13 C 0.6589(4) 0.64866(12) 0.47898(11) 0.0199(4) Uani 1 1 d . . . H13A H 0.5130 0.6601 0.4566 0.024 Uiso 1 1 calc R . . C14 C 0.6625(3) 0.46605(12) 0.40672(10) 0.0182(4) Uani 1 1 d . . . H14A H 0.7917 0.4440 0.4362 0.022 Uiso 1 1 calc R . . H14B H 0.5225 0.4702 0.4381 0.022 Uiso 1 1 calc R . . C15 C 0.6095(4) 0.41042(12) 0.34446(10) 0.0179(4) Uani 1 1 d . . . H15A H 0.4766 0.4319 0.3153 0.021 Uiso 1 1 calc R . . C16 C 0.5482(3) 0.32873(11) 0.36985(10) 0.0166(4) Uani 1 1 d . . . C17 C 0.3386(4) 0.29313(12) 0.34926(11) 0.0184(4) Uani 1 1 d . . . H17A H 0.2296 0.3218 0.3208 0.022 Uiso 1 1 calc R . . C18 C 0.2854(3) 0.21661(12) 0.36942(11) 0.0190(4) Uani 1 1 d . . . H18A H 0.1433 0.1929 0.3539 0.023 Uiso 1 1 calc R . . C19 C 0.4423(3) 0.17500(11) 0.41257(10) 0.0160(4) Uani 1 1 d . . . C20 C 0.6495(3) 0.21036(12) 0.43581(10) 0.0184(4) Uani 1 1 d . . . H20A H 0.7542 0.1826 0.4665 0.022 Uiso 1 1 calc R . . C21 C 0.7022(3) 0.28612(12) 0.41399(10) 0.0188(4) Uani 1 1 d . . . H21A H 0.8450 0.3095 0.4292 0.023 Uiso 1 1 calc R . . C22 C 0.2125(4) 0.05884(12) 0.40403(12) 0.0222(4) Uani 1 1 d . . . H22A H 0.2158 0.0036 0.4187 0.033 Uiso 1 1 calc R . . H22B H 0.2194 0.0623 0.3511 0.033 Uiso 1 1 calc R . . H22C H 0.0673 0.0832 0.4213 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.03955(15) 0.02417(13) 0.01822(13) -0.00176(7) -0.00058(11) -0.00105(12) O1 0.0218(7) 0.0170(7) 0.0182(6) 0.0013(5) -0.0016(6) -0.0022(5) N1 0.0240(9) 0.0164(8) 0.0184(8) -0.0007(7) 0.0042(7) 0.0001(7) C1 0.0162(10) 0.0221(10) 0.0161(9) 0.0040(7) -0.0030(8) 0.0021(8) C2 0.0215(10) 0.0267(11) 0.0172(10) 0.0022(8) -0.0005(9) 0.0039(9) C3 0.0187(10) 0.0401(13) 0.0169(10) 0.0049(9) -0.0002(8) 0.0003(10) C4 0.0269(12) 0.0312(12) 0.0211(11) 0.0066(9) -0.0017(9) -0.0111(10) C5 0.0274(13) 0.0262(11) 0.0199(10) 0.0030(8) -0.0022(9) -0.0058(9) C6 0.0184(9) 0.0214(10) 0.0145(9) 0.0019(8) -0.0034(8) 0.0002(8) C7 0.0182(10) 0.0188(10) 0.0178(10) 0.0022(8) -0.0004(9) 0.0004(8) C8 0.0213(10) 0.0142(9) 0.0172(10) 0.0035(8) 0.0013(8) -0.0023(8) C9 0.0198(10) 0.0205(9) 0.0211(9) -0.0006(7) 0.0021(9) 0.0004(9) C10 0.0199(10) 0.0218(10) 0.0188(10) 0.0030(8) -0.0015(8) -0.0035(8) C11 0.0281(11) 0.0164(9) 0.0158(9) 0.0015(8) 0.0009(8) -0.0055(8) C12 0.0255(11) 0.0155(10) 0.0237(10) 0.0006(8) 0.0057(9) 0.0026(8) C13 0.0194(10) 0.0184(9) 0.0220(10) 0.0043(8) 0.0006(8) 0.0013(8) C14 0.0182(9) 0.0194(10) 0.0169(9) 0.0002(8) 0.0025(8) 0.0001(9) C15 0.0173(9) 0.0192(10) 0.0172(9) 0.0014(8) -0.0024(8) 0.0003(8) C16 0.0192(10) 0.0176(9) 0.0132(8) -0.0006(7) 0.0014(8) -0.0005(8) C17 0.0161(9) 0.0228(10) 0.0162(9) 0.0023(8) -0.0019(7) 0.0017(9) C18 0.0160(9) 0.0228(10) 0.0183(10) -0.0025(8) -0.0003(8) -0.0013(9) C19 0.0182(10) 0.0174(9) 0.0123(8) -0.0011(7) 0.0029(7) 0.0013(8) C20 0.0187(9) 0.0216(10) 0.0148(9) 0.0005(8) -0.0011(8) 0.0019(9) C21 0.0169(9) 0.0220(10) 0.0176(9) -0.0024(8) -0.0003(8) 0.0004(9) C22 0.0222(11) 0.0194(10) 0.0251(11) -0.0007(8) -0.0014(9) -0.0044(9) _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 Br1 C11 1.908(2) . ? O1 C19 1.373(2) . ? O1 C22 1.433(3) . ? N1 C1 1.387(3) . ? N1 C15 1.464(3) . ? C1 C6 1.402(3) . ? C1 C2 1.408(3) . ? C2 C3 1.373(3) . ? C3 C4 1.390(3) . ? C4 C5 1.389(3) . ? C5 C6 1.399(3) . ? C6 C7 1.524(3) . ? C7 C8 1.518(3) . ? C7 C14 1.542(3) . ? C8 C13 1.390(3) . ? C8 C9 1.394(3) . ? C9 C10 1.391(3) . ? C10 C11 1.378(3) . ? C11 C12 1.383(3) . ? C12 C13 1.389(3) . ? C14 C15 1.520(3) . ? C15 C16 1.511(3) . ? C16 C17 1.394(3) . ? C16 C21 1.401(3) . ? C17 C18 1.390(3) . ? C18 C19 1.393(3) . ? C19 C20 1.394(3) . ? C20 C21 1.386(3) . ? 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 C19 O1 C22 116.05(15) . . ? C1 N1 C15 120.53(16) . . ? N1 C1 C6 121.79(17) . . ? N1 C1 C2 119.20(18) . . ? C6 C1 C2 118.97(19) . . ? C3 C2 C1 121.4(2) . . ? C2 C3 C4 120.1(2) . . ? C5 C4 C3 119.0(2) . . ? C4 C5 C6 121.9(2) . . ? C5 C6 C1 118.57(18) . . ? C5 C6 C7 121.17(18) . . ? C1 C6 C7 120.23(18) . . ? C8 C7 C6 114.33(17) . . ? C8 C7 C14 107.91(15) . . ? C6 C7 C14 110.51(16) . . ? C13 C8 C9 118.28(18) . . ? C13 C8 C7 120.53(18) . . ? C9 C8 C7 120.81(18) . . ? C10 C9 C8 121.12(19) . . ? C11 C10 C9 118.73(19) . . ? C10 C11 C12 121.95(19) . . ? C10 C11 Br1 118.88(15) . . ? C12 C11 Br1 119.17(15) . . ? C11 C12 C13 118.37(19) . . ? C12 C13 C8 121.55(19) . . ? C15 C14 C7 112.61(16) . . ? N1 C15 C16 108.69(16) . . ? N1 C15 C14 107.66(16) . . ? C16 C15 C14 112.74(16) . . ? C17 C16 C21 118.09(18) . . ? C17 C16 C15 121.05(18) . . ? C21 C16 C15 120.85(18) . . ? C18 C17 C16 121.54(19) . . ? C17 C18 C19 119.38(18) . . ? O1 C19 C18 124.35(18) . . ? O1 C19 C20 115.60(17) . . ? C18 C19 C20 120.05(18) . . ? C21 C20 C19 119.83(18) . . ? C20 C21 C16 121.05(18) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 65.94 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.328 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.052 data_cheny26 _database_code_depnum_ccdc_archive 'CCDC 812057' #TrackingRef 'CHENY26.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H16 Br N O' _chemical_formula_weight 330.22 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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.4384(3) _cell_length_b 5.3564(2) _cell_length_c 16.3563(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.619(2) _cell_angle_gamma 90.00 _cell_volume 737.82(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 112 _cell_measurement_theta_min 4 _cell_measurement_theta_max 85 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 3.745 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.760 _exptl_absorpt_correction_T_max 0.770 _exptl_absorpt_process_details SADABS _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_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 8916 _diffrn_reflns_av_R_equivalents 0.0492 _diffrn_reflns_av_sigmaI/netI 0.0456 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 65.65 _reflns_number_total 2324 _reflns_number_gt 1836 _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^)+(0.0591P)^2^+0.1621P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(4) _refine_ls_number_reflns 2324 _refine_ls_number_parameters 182 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1189 _refine_ls_wR_factor_gt 0.1099 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.28003(7) 0.46862(19) -0.11814(3) 0.0950(3) Uani 1 1 d . . . O1 O 0.5187(5) 0.3324(7) 0.3605(4) 0.0824(13) Uani 1 1 d . . . N1 N 0.2255(4) 0.9288(9) 0.2170(3) 0.0715(11) Uani 1 1 d . . . H1A H 0.1838 1.0747 0.2205 0.086 Uiso 1 1 calc R . . C1 C 0.2415(5) 0.8266(9) 0.1407(4) 0.0618(13) Uani 1 1 d . . . C2 C 0.1650(5) 0.9349(12) 0.0703(4) 0.0716(14) Uani 1 1 d . . . H2A H 0.1048 1.0787 0.0757 0.086 Uiso 1 1 calc R . . C3 C 0.1775(6) 0.8330(10) -0.0060(4) 0.0725(15) Uani 1 1 d . . . H3A H 0.1256 0.9057 -0.0519 0.087 Uiso 1 1 calc R . . C4 C 0.2674(5) 0.6226(10) -0.0135(3) 0.0683(14) Uani 1 1 d . . . C5 C 0.3488(5) 0.5130(10) 0.0535(3) 0.0629(13) Uani 1 1 d . . . H5A H 0.4116 0.3728 0.0467 0.075 Uiso 1 1 calc R . . C6 C 0.3354(5) 0.6146(9) 0.1307(3) 0.0576(11) Uani 1 1 d . . . C7 C 0.4246(5) 0.5019(9) 0.2047(3) 0.0616(12) Uani 1 1 d . . . H7A H 0.5296 0.4521 0.1898 0.074 Uiso 1 1 calc R . . H7B H 0.3694 0.3531 0.2211 0.074 Uiso 1 1 calc R . . C8 C 0.4412(5) 0.6801(8) 0.2764(3) 0.0596(12) Uani 1 1 d . . . H8A H 0.5117 0.8156 0.2612 0.072 Uiso 1 1 calc R . . C9 C 0.2766(5) 0.7986(8) 0.2914(3) 0.0618(12) Uani 1 1 d . . . H9A H 0.2939 0.9241 0.3346 0.074 Uiso 1 1 calc R . . C10 C 0.1557(5) 0.6129(10) 0.3200(4) 0.0619(12) Uani 1 1 d . . . C11 C 0.0337(5) 0.5218(10) 0.2684(3) 0.0710(15) Uani 1 1 d . . . H11A H 0.0253 0.5737 0.2141 0.085 Uiso 1 1 calc R . . C12 C -0.0749(7) 0.3575(12) 0.2952(5) 0.0883(19) Uani 1 1 d . . . H12A H -0.1572 0.3011 0.2594 0.106 Uiso 1 1 calc R . . C13 C -0.0632(7) 0.2749(13) 0.3747(5) 0.095(2) Uani 1 1 d . . . H13A H -0.1358 0.1604 0.3931 0.114 Uiso 1 1 calc R . . C14 C 0.0581(7) 0.3649(13) 0.4269(5) 0.093(2) Uani 1 1 d . . . H14A H 0.0684 0.3109 0.4810 0.111 Uiso 1 1 calc R . . C15 C 0.1634(6) 0.5340(11) 0.3988(4) 0.0798(18) Uani 1 1 d . . . H15A H 0.2429 0.5968 0.4351 0.096 Uiso 1 1 calc R . . C16 C 0.5171(6) 0.5574(10) 0.3534(5) 0.0643(15) Uani 1 1 d . . . C17 C 0.5944(7) 0.7201(11) 0.4166(4) 0.0887(18) Uani 1 1 d . . . H17A H 0.6028 0.6333 0.4680 0.133 Uiso 1 1 calc R . . H17B H 0.5322 0.8686 0.4218 0.133 Uiso 1 1 calc R . . H17C H 0.6985 0.7645 0.4010 0.133 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0903(4) 0.1095(5) 0.0864(4) 0.0080(5) 0.0156(3) -0.0037(5) O1 0.081(3) 0.054(3) 0.112(4) 0.010(2) -0.004(2) 0.008(2) N1 0.071(2) 0.038(2) 0.105(3) -0.002(3) -0.001(2) 0.012(2) C1 0.044(2) 0.043(2) 0.098(4) 0.006(3) 0.002(2) -0.003(2) C2 0.051(2) 0.051(3) 0.112(4) 0.016(4) -0.003(2) 0.009(3) C3 0.053(3) 0.063(3) 0.100(4) 0.026(3) -0.006(3) -0.008(2) C4 0.046(3) 0.064(3) 0.094(4) 0.020(3) -0.001(2) -0.010(2) C5 0.043(2) 0.056(4) 0.090(3) 0.007(3) 0.0106(19) 0.002(2) C6 0.045(2) 0.039(2) 0.088(3) 0.005(2) 0.003(2) 0.0013(19) C7 0.052(2) 0.043(3) 0.089(3) 0.000(3) 0.004(2) 0.008(2) C8 0.046(2) 0.041(3) 0.092(3) 0.002(2) 0.003(2) -0.0050(19) C9 0.056(3) 0.040(2) 0.090(4) -0.009(2) 0.002(2) -0.003(2) C10 0.044(2) 0.052(2) 0.090(4) -0.018(3) 0.009(2) 0.006(2) C11 0.047(2) 0.072(4) 0.094(3) -0.010(3) 0.006(2) -0.006(2) C12 0.056(3) 0.096(5) 0.113(5) -0.027(4) 0.008(3) -0.018(3) C13 0.066(4) 0.089(4) 0.132(6) -0.007(4) 0.023(4) -0.021(3) C14 0.064(3) 0.105(5) 0.110(5) 0.014(3) 0.012(3) -0.014(3) C15 0.050(3) 0.086(5) 0.104(4) -0.008(3) 0.006(3) -0.008(3) C16 0.045(3) 0.057(4) 0.091(4) 0.001(3) -0.001(3) 0.002(2) C17 0.086(4) 0.066(3) 0.111(5) -0.001(3) -0.023(4) -0.011(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 Br1 C4 1.908(6) . ? O1 C16 1.211(6) . ? N1 C1 1.378(7) . ? N1 C9 1.445(7) . ? C1 C6 1.400(7) . ? C1 C2 1.409(8) . ? C2 C3 1.372(8) . ? C3 C4 1.368(8) . ? C4 C5 1.387(7) . ? C5 C6 1.387(7) . ? C6 C7 1.510(6) . ? C7 C8 1.512(7) . ? C8 C16 1.526(8) . ? C8 C9 1.561(6) . ? C9 C10 1.520(7) . ? C10 C15 1.354(8) . ? C10 C11 1.379(7) . ? C11 C12 1.362(8) . ? C12 C13 1.372(10) . ? C13 C14 1.378(10) . ? C14 C15 1.368(8) . ? C16 C17 1.472(9) . ? 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 N1 C9 122.0(4) . . ? N1 C1 C6 121.1(5) . . ? N1 C1 C2 120.7(5) . . ? C6 C1 C2 118.2(6) . . ? C3 C2 C1 121.5(5) . . ? C4 C3 C2 119.0(5) . . ? C3 C4 C5 121.8(6) . . ? C3 C4 Br1 120.0(4) . . ? C5 C4 Br1 118.2(4) . . ? C6 C5 C4 119.3(5) . . ? C5 C6 C1 120.2(5) . . ? C5 C6 C7 120.5(4) . . ? C1 C6 C7 119.3(5) . . ? C6 C7 C8 112.7(4) . . ? C7 C8 C16 112.5(4) . . ? C7 C8 C9 109.8(4) . . ? C16 C8 C9 112.1(5) . . ? N1 C9 C10 113.9(4) . . ? N1 C9 C8 106.5(4) . . ? C10 C9 C8 113.8(4) . . ? C15 C10 C11 117.5(5) . . ? C15 C10 C9 120.3(5) . . ? C11 C10 C9 122.2(5) . . ? C12 C11 C10 121.5(6) . . ? C11 C12 C13 120.3(6) . . ? C12 C13 C14 118.7(6) . . ? C15 C14 C13 119.8(7) . . ? C10 C15 C14 122.2(6) . . ? O1 C16 C17 121.4(8) . . ? O1 C16 C8 120.6(7) . . ? C17 C16 C8 118.0(5) . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 65.65 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.470 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.053