# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_platon #TrackingRef 'N-2 Hydroxylated product.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H11 N O2' _chemical_formula_weight 213.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.9246(10) _cell_length_b 7.0228(6) _cell_length_c 14.1338(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.645(6) _cell_angle_gamma 90.00 _cell_volume 1084.29(16) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.975 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_process_details SADBAS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 10387 _diffrn_reflns_av_R_equivalents 0.0527 _diffrn_reflns_av_sigmaI/netI 0.0557 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 27.22 _reflns_number_total 2385 _reflns_number_gt 1350 _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^)+(0.0798P)^2^+1.1887P] 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 2254 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1433 _refine_ls_R_factor_gt 0.0789 _refine_ls_wR_factor_ref 0.2512 _refine_ls_wR_factor_gt 0.2155 _refine_ls_goodness_of_fit_ref 1.174 _refine_ls_restrained_S_all 1.174 _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 O1 O 0.5429(3) 0.5962(4) 0.24874(16) 0.0601(9) Uani 1 1 d . . . O3 O 0.5256(3) 0.8089(4) -0.07195(17) 0.0693(10) Uani 1 1 d . . . H3A H 0.5360 0.8328 -0.1281 0.104 Uiso 1 1 d R . . N1 N 0.5048(3) 0.6714(4) 0.09635(18) 0.0502(9) Uani 1 1 d . . . H1 H 0.4469 0.6963 0.0565 0.060 Uiso 1 1 d R . . C1 C 0.4696(4) 0.6415(5) 0.1859(2) 0.0465(10) Uani 1 1 d . . . C2 C 0.3365(4) 0.6635(5) 0.2048(2) 0.0463(10) Uani 1 1 d . . . C3 C 0.2579(4) 0.7662(6) 0.1465(3) 0.0604(12) Uani 1 1 d . . . H3 H 0.2878 0.8240 0.0922 0.072 Uiso 1 1 calc R . . C4 C 0.1354(5) 0.7834(7) 0.1683(3) 0.0762(14) Uani 1 1 d . . . H4 H 0.0832 0.8535 0.1292 0.091 Uiso 1 1 calc R . . C5 C 0.0910(5) 0.6967(8) 0.2478(4) 0.0791(15) Uani 1 1 d . . . H5 H 0.0085 0.7074 0.2622 0.095 Uiso 1 1 calc R . . C6 C 0.1672(5) 0.5945(7) 0.3063(3) 0.0777(15) Uani 1 1 d . . . H6 H 0.1364 0.5361 0.3601 0.093 Uiso 1 1 calc R . . C7 C 0.2903(5) 0.5785(6) 0.2850(3) 0.0612(12) Uani 1 1 d . . . H7 H 0.3422 0.5100 0.3250 0.073 Uiso 1 1 calc R . . C8 C 0.6238(4) 0.6683(5) 0.0582(2) 0.0445(9) Uani 1 1 d . . . C9 C 0.6313(4) 0.7444(5) -0.0330(2) 0.0492(10) Uani 1 1 d . . . C10 C 0.7443(5) 0.7485(6) -0.0775(3) 0.0581(11) Uani 1 1 d . . . H10 H 0.7508 0.7991 -0.1381 0.070 Uiso 1 1 calc R . . C11 C 0.8460(5) 0.6782(7) -0.0320(3) 0.0701(13) Uani 1 1 d . . . H11 H 0.9215 0.6827 -0.0617 0.084 Uiso 1 1 calc R . . C12 C 0.8376(5) 0.6007(7) 0.0573(3) 0.0716(14) Uani 1 1 d . . . H12 H 0.9072 0.5527 0.0873 0.086 Uiso 1 1 calc R . . C13 C 0.7251(4) 0.5943(6) 0.1027(3) 0.0587(11) Uani 1 1 d . . . H13 H 0.7188 0.5403 0.1626 0.070 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.065(2) 0.0783(19) 0.0365(12) 0.0027(12) -0.0038(12) 0.0157(16) O3 0.082(3) 0.088(2) 0.0375(13) 0.0124(13) -0.0003(13) 0.0128(18) N1 0.054(2) 0.0614(19) 0.0353(14) 0.0035(12) -0.0041(14) 0.0026(16) C1 0.064(3) 0.0387(18) 0.0370(16) -0.0031(13) -0.0012(16) -0.0009(18) C2 0.054(3) 0.0415(18) 0.0434(18) -0.0048(14) 0.0035(17) -0.0019(18) C3 0.065(3) 0.057(2) 0.059(2) 0.0068(18) 0.005(2) 0.005(2) C4 0.074(4) 0.074(3) 0.081(3) 0.003(2) 0.001(3) 0.010(3) C5 0.066(4) 0.083(3) 0.089(3) -0.009(3) 0.016(3) -0.010(3) C6 0.085(4) 0.081(3) 0.067(3) 0.004(2) 0.019(3) -0.018(3) C7 0.074(4) 0.058(2) 0.052(2) 0.0042(17) 0.009(2) -0.006(2) C8 0.052(3) 0.0448(19) 0.0362(16) -0.0048(14) 0.0012(16) -0.0012(18) C9 0.065(3) 0.0454(19) 0.0371(17) -0.0032(14) -0.0015(17) 0.0013(19) C10 0.070(3) 0.055(2) 0.049(2) -0.0009(17) 0.013(2) 0.001(2) C11 0.068(4) 0.072(3) 0.071(3) -0.007(2) 0.015(2) 0.005(3) C12 0.065(4) 0.078(3) 0.071(3) -0.004(2) -0.006(2) 0.018(3) C13 0.066(3) 0.063(2) 0.047(2) 0.0021(17) -0.0010(19) 0.013(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.231(4) . ? O3 C9 1.352(5) . ? O3 H3A 0.8201 . ? N1 C1 1.343(4) . ? N1 C8 1.414(5) . ? N1 H1 0.8600 . ? C1 C2 1.489(6) . ? C2 C7 1.381(5) . ? C2 C3 1.387(5) . ? C3 C4 1.382(6) . ? C3 H3 0.9300 . ? C4 C5 1.372(7) . ? C4 H4 0.9300 . ? C5 C6 1.369(7) . ? C5 H5 0.9300 . ? C6 C7 1.387(7) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C13 1.369(6) . ? C8 C9 1.398(5) . ? C9 C10 1.392(6) . ? C10 C11 1.369(6) . ? C10 H10 0.9300 . ? C11 C12 1.379(6) . ? C11 H11 0.9300 . ? C12 C13 1.394(6) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? 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 C9 O3 H3A 109.6 . . ? C1 N1 C8 129.1(3) . . ? C1 N1 H1 115.6 . . ? C8 N1 H1 115.2 . . ? O1 C1 N1 122.0(4) . . ? O1 C1 C2 121.7(3) . . ? N1 C1 C2 116.3(3) . . ? C7 C2 C3 118.9(4) . . ? C7 C2 C1 118.0(4) . . ? C3 C2 C1 123.2(3) . . ? C4 C3 C2 120.5(4) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C5 C4 C3 119.7(5) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C6 C5 C4 120.7(5) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 119.7(4) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C2 C7 C6 120.5(4) . . ? C2 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C13 C8 C9 120.9(4) . . ? C13 C8 N1 124.9(3) . . ? C9 C8 N1 114.2(3) . . ? O3 C9 C10 124.5(3) . . ? O3 C9 C8 116.4(4) . . ? C10 C9 C8 119.1(4) . . ? C11 C10 C9 119.9(4) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 120.7(4) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C11 C12 C13 120.1(4) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C8 C13 C12 119.2(4) . . ? C8 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.22 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.259 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.064 _database_code_depnum_ccdc_archive 'CCDC 919286' ####################################################################### # # 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_n-1_Benzoxazoles #TrackingRef 'N-1-benzoxazoles.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H10 Br N O' _chemical_formula_weight 288.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.3512(8) _cell_length_b 14.0265(11) _cell_length_c 12.8571(10) _cell_angle_alpha 90.00 _cell_angle_beta 105.177(5) _cell_angle_gamma 90.00 _cell_volume 1801.6(2) _cell_formula_units_Z 6 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.52 _cell_measurement_theta_max 21.24 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.593 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 3.403 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details SADBAS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 21797 _diffrn_reflns_av_R_equivalents 0.0833 _diffrn_reflns_av_sigmaI/netI 0.1461 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 28.54 _reflns_number_total 7274 _reflns_number_gt 3248 _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^)+(0.1030P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0029(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.57(2) _refine_ls_number_reflns 7274 _refine_ls_number_parameters 464 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1695 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1897 _refine_ls_wR_factor_gt 0.1374 _refine_ls_goodness_of_fit_ref 0.890 _refine_ls_restrained_S_all 0.890 _refine_ls_shift/su_max 0.868 _refine_ls_shift/su_mean 0.039 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 1.09315(11) 0.00619(7) 0.23184(10) 0.0674(4) Uani 1 1 d . . . Br2 Br 0.41203(11) 0.74593(8) 0.26484(9) 0.0644(4) Uani 1 1 d . . . Br3 Br 1.07244(10) 0.69171(9) 0.22284(9) 0.0709(4) Uani 1 1 d . . . C4 C 0.5812(10) 0.7096(8) 0.3548(10) 0.050(3) Uani 1 1 d . . . C5 C 0.6586(11) 0.6439(7) 0.3194(9) 0.041(3) Uani 1 1 d . . . C6 C 0.7798(11) 0.6170(7) 0.3872(10) 0.047(3) Uani 1 1 d . . . C3 C 0.6292(11) 0.7492(9) 0.4561(10) 0.052(3) Uani 1 1 d . . . H3 H 0.5780 0.7950 0.4792 0.063 Uiso 1 1 calc R . . C1 C 0.8319(12) 0.6547(8) 0.4913(11) 0.056(3) Uani 1 1 d . . . H1 H 0.9142 0.6357 0.5353 0.067 Uiso 1 1 calc R . . C2 C 0.7515(12) 0.7228(8) 0.5243(9) 0.053(3) Uani 1 1 d . . . C7 C 0.7786(11) 0.4735(6) 0.1630(9) 0.048(3) Uani 1 1 d . . . C12 C 0.8980(12) 0.4240(8) 0.1883(9) 0.059(3) Uani 1 1 d . . . H12 H 0.9609 0.4332 0.2540 0.070 Uiso 1 1 calc R . . C8 C 0.6842(13) 0.4578(8) 0.0630(10) 0.061(3) Uani 1 1 d . . . H8 H 0.6032 0.4905 0.0449 0.073 Uiso 1 1 calc R . . C11 C 0.9223(15) 0.3579(10) 0.1103(13) 0.075(4) Uani 1 1 d . . . H11 H 1.0018 0.3234 0.1274 0.090 Uiso 1 1 calc R . . C10 C 0.8366(16) 0.3436(12) 0.0149(12) 0.074(4) Uani 1 1 d . . . H10 H 0.8576 0.3022 -0.0348 0.089 Uiso 1 1 calc R . . C9 C 0.7166(17) 0.3909(10) -0.0090(12) 0.077(5) Uani 1 1 d . . . H9 H 0.6546 0.3789 -0.0744 0.093 Uiso 1 1 calc R . . C13 C 0.7504(12) 0.5421(7) 0.2422(10) 0.057(3) Uani 1 1 d . . . C14 C 0.7367(11) 0.2854(7) 0.3439(9) 0.045(3) Uani 1 1 d . . . C19 C 0.6224(12) 0.3380(10) 0.3225(10) 0.060(3) Uani 1 1 d . . . H19 H 0.5624 0.3321 0.2549 0.072 Uiso 1 1 calc R . . C15 C 0.8273(13) 0.2956(9) 0.4426(11) 0.065(3) Uani 1 1 d . . . H15 H 0.9063 0.2606 0.4582 0.078 Uiso 1 1 calc R . . C18 C 0.5916(14) 0.3976(9) 0.3931(11) 0.065(4) Uani 1 1 d . . . H18 H 0.5112 0.4311 0.3765 0.078 Uiso 1 1 calc R . . C16 C 0.8030(14) 0.3562(11) 0.5181(9) 0.069(4) Uani 1 1 d . . . H16 H 0.8645 0.3626 0.5849 0.082 Uiso 1 1 calc R . . C17 C 0.6846(14) 0.4081(9) 0.4933(12) 0.066(4) Uani 1 1 d . . . H17 H 0.6670 0.4502 0.5438 0.079 Uiso 1 1 calc R . . C24 C 0.9257(11) 0.0458(8) 0.1430(9) 0.048(3) Uani 1 1 d . . . C25 C 0.8495(12) 0.1140(8) 0.1814(10) 0.053(3) Uani 1 1 d . . . C20 C 0.7275(12) 0.1396(8) 0.1129(11) 0.056(3) Uani 1 1 d . . . C22 C 0.8751(13) 0.0064(9) 0.0427(10) 0.057(3) Uani 1 1 d . . . H22 H 0.9244 -0.0401 0.0185 0.069 Uiso 1 1 calc R . . C26 C 0.7633(11) 0.2173(7) 0.2663(9) 0.044(3) Uani 1 1 d . . . C21 C 0.6743(13) 0.1023(8) 0.0112(11) 0.053(3) Uani 1 1 d . . . H21 H 0.5912 0.1218 -0.0311 0.064 Uiso 1 1 calc R . . C23 C 0.7495(14) 0.0350(8) -0.0249(10) 0.062(4) Uani 1 1 d . . . O1 O 0.6385(10) 0.5931(6) 0.2265(8) 0.078(3) Uani 1 1 d . . . N1 N 0.8406(7) 0.5520(6) 0.3375(6) 0.0307(18) Uani 1 1 d . . . C30 C 0.9002(10) 0.7266(8) 0.1426(10) 0.050(3) Uani 1 1 d . . . C31 C 0.8252(11) 0.7931(7) 0.1806(9) 0.046(3) Uani 1 1 d . . . C28 C 0.7154(12) 0.7110(8) -0.0213(9) 0.053(3) Uani 1 1 d . . . C27 C 0.6409(12) 0.7775(7) 0.0184(9) 0.057(3) Uani 1 1 d . . . H27 H 0.5559 0.7958 -0.0211 0.068 Uiso 1 1 calc R . . C32 C 0.6992(11) 0.8157(7) 0.1198(9) 0.048(3) Uani 1 1 d . . . C29 C 0.8435(11) 0.6859(9) 0.0422(10) 0.055(3) Uani 1 1 d . . . H29 H 0.8922 0.6403 0.0161 0.065 Uiso 1 1 calc R . . O2 O 0.6733(7) 0.2070(5) 0.1682(6) 0.0536(19) Uani 1 1 d . . . C36 C 0.5933(13) 1.0058(10) 0.3340(10) 0.067(4) Uani 1 1 d . . . H36 H 0.5259 0.9947 0.2715 0.080 Uiso 1 1 calc R . . C37 C 0.7174(12) 0.9610(8) 0.3489(9) 0.052(3) Uani 1 1 d . . . C33 C 0.7940(18) 1.0398(11) 0.5192(12) 0.091(5) Uani 1 1 d . . . H33 H 0.8619 1.0520 0.5813 0.109 Uiso 1 1 calc R . . C35 C 0.5701(15) 1.0673(10) 0.4127(12) 0.076(4) Uani 1 1 d . . . H35 H 0.4873 1.0968 0.4027 0.091 Uiso 1 1 calc R . . C34 C 0.670(2) 1.0839(11) 0.5043(14) 0.096(5) Uani 1 1 d . . . H34 H 0.6542 1.1247 0.5569 0.115 Uiso 1 1 calc R . . C38 C 0.8163(14) 0.9790(8) 0.4431(10) 0.071(4) Uani 1 1 d . . . H38 H 0.8990 0.9492 0.4543 0.085 Uiso 1 1 calc R . . C39 C 0.7433(13) 0.8960(7) 0.2685(11) 0.058(4) Uani 1 1 d . . . O3 O 0.8517(9) 0.8433(7) 0.2783(7) 0.077(2) Uani 1 1 d . . . N2 N 0.6469(8) 0.8831(5) 0.1763(6) 0.034(2) Uani 1 1 d . . . N3 N 0.8727(10) 0.1649(6) 0.2792(7) 0.051(2) Uani 1 1 d . . . C40 C 0.6981(12) -0.0099(9) -0.1343(9) 0.078(4) Uani 1 1 d . . . H40A H 0.6032 -0.0001 -0.1593 0.117 Uiso 1 1 calc R . . H40B H 0.7168 -0.0771 -0.1294 0.117 Uiso 1 1 calc R . . H40C H 0.7416 0.0188 -0.1839 0.117 Uiso 1 1 calc R . . C41 C 0.6576(11) 0.6635(8) -0.1293(9) 0.070(3) Uani 1 1 d . . . H41A H 0.5634 0.6766 -0.1532 0.105 Uiso 1 1 calc R . . H41B H 0.6713 0.5959 -0.1221 0.105 Uiso 1 1 calc R . . H41C H 0.7013 0.6878 -0.1810 0.105 Uiso 1 1 calc R . . C42 C 0.7994(13) 0.7694(9) 0.6327(10) 0.078(4) Uani 1 1 d . . . H42A H 0.8478 0.8264 0.6260 0.117 Uiso 1 1 calc R . . H42B H 0.8570 0.7263 0.6817 0.117 Uiso 1 1 calc R . . H42C H 0.7238 0.7851 0.6596 0.117 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 0.0535(8) 0.0674(6) 0.0772(9) 0.0125(7) 0.0098(7) 0.0066(6) Br2 0.0479(8) 0.0722(7) 0.0672(8) 0.0108(7) 0.0047(6) 0.0063(6) Br3 0.0495(7) 0.0782(7) 0.0798(9) 0.0148(7) 0.0080(6) 0.0105(6) C4 0.036(6) 0.050(8) 0.062(9) 0.019(6) 0.011(6) -0.008(5) C5 0.040(7) 0.046(6) 0.033(7) -0.004(5) 0.003(6) -0.012(5) C6 0.045(7) 0.039(6) 0.048(8) 0.019(6) -0.003(6) -0.007(5) C3 0.045(7) 0.054(6) 0.057(8) 0.018(7) 0.011(6) 0.005(6) C1 0.047(8) 0.051(7) 0.062(9) 0.003(7) 0.000(7) 0.003(6) C2 0.053(8) 0.053(9) 0.048(8) 0.014(5) 0.003(6) -0.009(6) C7 0.049(7) 0.032(6) 0.062(8) 0.000(5) 0.010(7) 0.001(5) C12 0.072(9) 0.056(7) 0.044(8) 0.002(6) 0.009(7) 0.000(7) C8 0.068(9) 0.057(8) 0.055(8) -0.005(7) 0.012(7) -0.009(6) C11 0.082(11) 0.056(8) 0.104(12) -0.010(9) 0.056(10) -0.003(8) C10 0.087(11) 0.069(8) 0.075(10) -0.018(9) 0.036(9) -0.005(9) C9 0.088(12) 0.083(11) 0.065(10) -0.017(8) 0.028(9) -0.021(9) C13 0.062(10) 0.049(7) 0.064(10) 0.007(7) 0.026(8) 0.000(6) C14 0.035(7) 0.061(7) 0.036(7) 0.008(5) 0.006(6) -0.003(5) C19 0.057(8) 0.064(8) 0.054(8) -0.005(7) 0.006(7) -0.021(7) C15 0.058(9) 0.065(7) 0.068(9) -0.005(7) 0.010(8) 0.006(6) C18 0.065(10) 0.066(9) 0.061(10) 0.004(7) 0.011(8) 0.005(6) C16 0.087(10) 0.060(8) 0.047(8) -0.009(7) -0.004(7) -0.006(8) C17 0.069(9) 0.054(8) 0.080(10) -0.002(7) 0.029(9) -0.003(7) C24 0.046(7) 0.040(6) 0.053(8) 0.000(6) 0.000(6) 0.004(5) C25 0.064(9) 0.039(6) 0.051(8) 0.017(6) 0.010(7) 0.001(6) C20 0.059(8) 0.055(7) 0.055(9) 0.006(7) 0.019(7) 0.002(6) C22 0.071(9) 0.045(6) 0.054(8) -0.017(7) 0.012(7) -0.003(7) C26 0.049(7) 0.045(6) 0.032(7) -0.005(5) -0.001(6) -0.013(5) C21 0.059(8) 0.054(7) 0.039(8) 0.004(6) 0.001(6) -0.006(6) C23 0.083(10) 0.046(8) 0.056(9) -0.010(6) 0.016(8) -0.003(6) O1 0.068(6) 0.071(6) 0.090(8) 0.003(5) 0.012(6) -0.004(5) N1 0.027(5) 0.040(4) 0.019(5) 0.001(4) -0.004(4) 0.002(4) C30 0.036(6) 0.060(8) 0.052(8) 0.016(6) 0.007(6) 0.004(5) C31 0.050(7) 0.044(6) 0.047(7) 0.003(5) 0.018(6) -0.006(5) C28 0.056(7) 0.055(8) 0.049(8) -0.006(6) 0.017(6) 0.007(6) C27 0.056(8) 0.060(7) 0.055(8) 0.011(6) 0.017(7) 0.004(6) C32 0.044(7) 0.058(7) 0.038(7) -0.006(5) 0.003(6) 0.000(5) C29 0.057(7) 0.047(6) 0.071(9) -0.005(7) 0.036(7) 0.003(6) O2 0.051(5) 0.049(5) 0.057(5) -0.004(4) 0.009(4) 0.000(4) C36 0.071(9) 0.063(7) 0.072(9) 0.001(7) 0.029(7) -0.014(7) C37 0.061(8) 0.042(6) 0.053(8) -0.002(6) 0.013(7) -0.007(6) C33 0.110(14) 0.078(12) 0.073(12) -0.029(9) 0.004(10) -0.009(10) C35 0.093(11) 0.063(8) 0.080(11) -0.012(8) 0.036(9) -0.014(8) C34 0.123(15) 0.085(11) 0.091(13) -0.023(9) 0.050(12) -0.011(10) C38 0.091(11) 0.052(8) 0.058(9) -0.002(7) -0.002(8) -0.005(6) C39 0.048(8) 0.046(7) 0.080(11) 0.015(7) 0.015(8) -0.003(6) O3 0.073(6) 0.075(5) 0.080(7) 0.007(6) 0.016(5) -0.014(6) N2 0.029(5) 0.038(4) 0.030(5) 0.001(4) 0.001(4) 0.005(3) N3 0.057(6) 0.044(5) 0.047(6) -0.004(4) 0.007(5) -0.009(4) C40 0.098(11) 0.063(8) 0.067(9) 0.001(7) 0.012(8) 0.018(7) C41 0.065(8) 0.080(9) 0.058(8) -0.016(6) 0.006(6) 0.012(6) C42 0.075(9) 0.078(10) 0.074(10) -0.016(8) 0.006(8) -0.008(7) _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 C24 1.892(10) . ? Br2 C4 1.898(11) . ? Br3 C30 1.876(10) . ? C4 C5 1.374(15) . ? C4 C3 1.383(15) . ? C5 O1 1.360(13) . ? C5 C6 1.380(14) . ? C6 N1 1.359(13) . ? C6 C1 1.408(16) . ? C3 C2 1.388(14) . ? C1 C2 1.403(15) . ? C2 C42 1.501(16) . ? C7 C8 1.414(15) . ? C7 C12 1.380(14) . ? C7 C13 1.485(14) . ? C12 C11 1.436(17) . ? C8 C9 1.418(17) . ? C11 C10 1.328(17) . ? C10 C9 1.371(19) . ? C13 O1 1.331(12) . ? C13 N1 1.338(13) . ? C14 C19 1.361(15) . ? C14 C15 1.374(16) . ? C14 C26 1.458(15) . ? C19 C18 1.333(16) . ? C15 C16 1.361(17) . ? C18 C17 1.400(17) . ? C16 C17 1.389(19) . ? C24 C22 1.375(15) . ? C24 C25 1.410(15) . ? C25 C20 1.385(15) . ? C25 N3 1.410(14) . ? C20 O2 1.387(13) . ? C20 C21 1.382(17) . ? C22 C23 1.420(16) . ? C26 N3 1.324(12) . ? C26 O2 1.366(12) . ? C21 C23 1.379(16) . ? C23 C40 1.505(16) . ? C30 C31 1.382(15) . ? C30 C29 1.392(15) . ? C31 C32 1.371(14) . ? C31 O3 1.403(13) . ? C28 C27 1.390(14) . ? C28 C29 1.408(15) . ? C28 C41 1.515(14) . ? C27 C32 1.392(14) . ? C32 N2 1.387(12) . ? C36 C37 1.397(16) . ? C36 C35 1.396(17) . ? C37 C38 1.389(15) . ? C37 C39 1.455(15) . ? C33 C38 1.363(17) . ? C33 C34 1.40(2) . ? C35 C34 1.367(19) . ? C39 O3 1.323(13) . ? C39 N2 1.347(14) . ? 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 C5 C4 C3 119.0(10) . . ? C5 C4 Br2 120.2(9) . . ? C3 C4 Br2 120.8(9) . . ? O1 C5 C6 108.4(10) . . ? O1 C5 C4 132.4(11) . . ? C6 C5 C4 119.1(11) . . ? N1 C6 C5 110.0(10) . . ? N1 C6 C1 126.1(10) . . ? C5 C6 C1 123.8(11) . . ? C2 C3 C4 122.1(12) . . ? C2 C1 C6 115.6(11) . . ? C3 C2 C1 120.4(12) . . ? C3 C2 C42 119.7(12) . . ? C1 C2 C42 119.9(11) . . ? C8 C7 C12 120.0(11) . . ? C8 C7 C13 120.8(10) . . ? C12 C7 C13 119.2(11) . . ? C7 C12 C11 118.0(11) . . ? C7 C8 C9 118.1(13) . . ? C10 C11 C12 123.1(14) . . ? C9 C10 C11 118.7(15) . . ? C10 C9 C8 122.0(14) . . ? O1 C13 N1 117.0(11) . . ? O1 C13 C7 124.3(12) . . ? N1 C13 C7 118.7(11) . . ? C19 C14 C15 118.5(11) . . ? C19 C14 C26 121.8(11) . . ? C15 C14 C26 119.7(10) . . ? C14 C19 C18 123.5(12) . . ? C16 C15 C14 121.0(12) . . ? C19 C18 C17 117.6(12) . . ? C15 C16 C17 118.7(12) . . ? C16 C17 C18 120.6(13) . . ? C22 C24 C25 119.4(11) . . ? C22 C24 Br1 120.8(9) . . ? C25 C24 Br1 119.7(9) . . ? C20 C25 C24 117.0(11) . . ? C20 C25 N3 110.5(10) . . ? C24 C25 N3 132.5(11) . . ? O2 C20 C25 105.9(11) . . ? O2 C20 C21 129.0(12) . . ? C25 C20 C21 125.1(11) . . ? C24 C22 C23 121.6(11) . . ? N3 C26 O2 114.3(10) . . ? N3 C26 C14 125.9(10) . . ? O2 C26 C14 119.7(10) . . ? C23 C21 C20 117.3(12) . . ? C21 C23 C22 119.7(11) . . ? C21 C23 C40 120.6(12) . . ? C22 C23 C40 119.8(11) . . ? C13 O1 C5 102.8(10) . . ? C6 N1 C13 101.7(9) . . ? C31 C30 C29 117.7(10) . . ? C31 C30 Br3 121.5(9) . . ? C29 C30 Br3 120.8(9) . . ? C32 C31 C30 119.5(11) . . ? C32 C31 O3 109.2(10) . . ? C30 C31 O3 131.3(11) . . ? C27 C28 C29 118.9(11) . . ? C27 C28 C41 120.5(10) . . ? C29 C28 C41 120.5(10) . . ? C28 C27 C32 117.1(11) . . ? C31 C32 N2 107.6(9) . . ? C31 C32 C27 124.0(10) . . ? N2 C32 C27 128.3(10) . . ? C30 C29 C28 122.7(10) . . ? C26 O2 C20 106.0(9) . . ? C37 C36 C35 120.3(13) . . ? C36 C37 C38 118.6(12) . . ? C36 C37 C39 121.2(12) . . ? C38 C37 C39 120.2(12) . . ? C38 C33 C34 120.1(14) . . ? C34 C35 C36 119.7(14) . . ? C35 C34 C33 120.1(15) . . ? C33 C38 C37 121.0(14) . . ? O3 C39 N2 115.0(10) . . ? O3 C39 C37 126.4(12) . . ? N2 C39 C37 118.5(11) . . ? C39 O3 C31 103.5(9) . . ? C39 N2 C32 104.6(8) . . ? C26 N3 C25 103.2(9) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.54 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.411 _refine_diff_density_min -0.625 _refine_diff_density_rms 0.093 _database_code_depnum_ccdc_archive 'CCDC 919285'