# 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_a13864 _database_code_depnum_ccdc_archive 'CCDC 892806' #TrackingRef 'web_deposit_cif_file_0_UtpalDas_1342697118.D411.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H12 Br N O4' _chemical_formula_sum 'C17 H10 Br N O4' _chemical_formula_weight 372.17 _chemical_absolute_configuration ad 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 9.2201(4) _cell_length_b 5.4993(3) _cell_length_c 14.8584(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.833(3) _cell_angle_gamma 90.00 _cell_volume 751.70(7) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.74 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.644 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 2.754 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2351 _exptl_absorpt_correction_T_max 0.8746 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 4284 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0608 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -3 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 25.05 _reflns_number_total 1915 _reflns_number_gt 1594 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0000P)^2^+1.7054P] 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 0.020(15) _refine_ls_number_reflns 1915 _refine_ls_number_parameters 208 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0451 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0825 _refine_ls_wR_factor_gt 0.0564 _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_restrained_S_all 0.964 _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 C1 C 0.3340(6) 0.4970(12) 0.5760(4) 0.0290(17) Uani 1 1 d . . . C2 C 0.4462(6) 0.6566(11) 0.5717(4) 0.0284(15) Uani 1 1 d . . . H2 H 0.4343 0.8005 0.5366 0.034 Uiso 1 1 calc R . . C3 C 0.5785(6) 0.6079(14) 0.6190(3) 0.0283(15) Uani 1 1 d . . . H3 H 0.6567 0.7197 0.6169 0.034 Uiso 1 1 calc R . . C4 C 0.5959(6) 0.3959(11) 0.6691(3) 0.0214(13) Uani 1 1 d . . . C5 C 0.4809(6) 0.2363(11) 0.6710(4) 0.0240(14) Uani 1 1 d . . . H5 H 0.4924 0.0908 0.7052 0.029 Uiso 1 1 calc R . . C6 C 0.3495(6) 0.2828(12) 0.6242(4) 0.0267(14) Uani 1 1 d . . . H6 H 0.2715 0.1702 0.6251 0.032 Uiso 1 1 calc R . . C7 C 0.7348(6) 0.3310(12) 0.7211(3) 0.0240(14) Uani 1 1 d . . . H7 H 0.7580 0.1535 0.7191 0.029 Uiso 1 1 calc R . . C8 C 0.8654(6) 0.4881(11) 0.7297(3) 0.0271(15) Uani 1 1 d . . . H8 H 0.8562 0.6512 0.7001 0.033 Uiso 1 1 calc R . . C9 C 0.7826(6) 0.4537(11) 0.8135(4) 0.0224(14) Uani 1 1 d . . . C10 C 0.7008(6) 0.6608(11) 0.8498(4) 0.0257(15) Uani 1 1 d . . . C11 C 0.7019(6) 0.6176(13) 0.9488(3) 0.0241(15) Uani 1 1 d . . . C12 C 0.6384(7) 0.7616(13) 1.0122(4) 0.0336(16) Uani 1 1 d . . . H12 H 0.5854 0.9047 0.9955 0.040 Uiso 1 1 calc R . . C13 C 0.6566(7) 0.6846(13) 1.1013(4) 0.0391(18) Uani 1 1 d . . . H13 H 0.6156 0.7784 1.1469 0.047 Uiso 1 1 calc R . . C14 C 0.7324(7) 0.4760(14) 1.1255(4) 0.0399(19) Uani 1 1 d . . . H14 H 0.7412 0.4286 1.1871 0.048 Uiso 1 1 calc R . . C15 C 0.7964(6) 0.3330(13) 1.0616(4) 0.0312(15) Uani 1 1 d . . . H15 H 0.8495 0.1900 1.0782 0.037 Uiso 1 1 calc R . . C16 C 0.7789(6) 0.4096(11) 0.9727(3) 0.0241(14) Uani 1 1 d . . . C17 C 0.8361(6) 0.2949(12) 0.8920(4) 0.0260(14) Uani 1 1 d . . . N1 N 1.0099(6) 0.3712(13) 0.7296(3) 0.0369(15) Uani 1 1 d . . . O1 O 1.0208(5) 0.1686(10) 0.6986(3) 0.0474(14) Uani 1 1 d . . . O2 O 1.1126(4) 0.4927(9) 0.7598(3) 0.0512(16) Uani 1 1 d . . . O3 O 0.6459(4) 0.8292(8) 0.8081(2) 0.0333(11) Uani 1 1 d . . . O4 O 0.9091(4) 0.1142(10) 0.8884(2) 0.0395(13) Uani 1 1 d . . . Br1 Br 0.15425(6) 0.56664(16) 0.51021(4) 0.0501(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.019(3) 0.042(5) 0.025(3) 0.000(3) -0.004(2) 0.009(3) C2 0.037(4) 0.024(4) 0.023(3) 0.006(3) -0.002(3) 0.006(3) C3 0.030(3) 0.029(4) 0.024(3) 0.007(3) -0.005(2) -0.001(3) C4 0.027(3) 0.021(4) 0.016(3) 0.000(2) 0.000(2) 0.005(3) C5 0.025(3) 0.023(4) 0.024(3) 0.003(3) -0.001(2) 0.001(3) C6 0.023(3) 0.028(4) 0.029(3) 0.005(3) 0.005(3) 0.002(3) C7 0.025(3) 0.024(4) 0.023(3) -0.003(3) 0.000(2) 0.000(3) C8 0.025(3) 0.035(4) 0.020(3) -0.002(3) -0.006(2) 0.002(3) C9 0.016(3) 0.027(4) 0.024(3) 0.002(3) -0.003(2) 0.003(3) C10 0.018(3) 0.029(4) 0.028(3) -0.001(3) -0.006(3) -0.006(3) C11 0.021(3) 0.029(5) 0.023(3) 0.003(3) 0.001(2) -0.003(3) C12 0.037(4) 0.033(4) 0.031(3) 0.001(3) 0.003(3) -0.003(3) C13 0.045(4) 0.044(5) 0.029(4) -0.008(3) 0.003(3) -0.006(4) C14 0.050(4) 0.053(5) 0.016(3) 0.003(3) -0.004(3) -0.006(4) C15 0.028(3) 0.036(4) 0.028(3) 0.005(3) -0.006(3) -0.006(3) C16 0.020(3) 0.033(4) 0.019(3) 0.000(3) -0.003(2) -0.004(3) C17 0.022(3) 0.030(4) 0.026(3) 0.000(3) -0.003(2) 0.000(3) N1 0.027(3) 0.057(5) 0.027(3) 0.001(3) 0.003(2) 0.004(3) O1 0.034(3) 0.062(4) 0.047(3) -0.004(3) 0.006(2) 0.011(2) O2 0.027(2) 0.076(5) 0.049(3) -0.014(3) -0.004(2) -0.006(3) O3 0.047(3) 0.024(3) 0.028(2) 0.005(2) -0.005(2) 0.006(2) O4 0.037(2) 0.045(4) 0.036(2) 0.006(2) -0.0020(17) 0.019(3) Br1 0.0290(3) 0.0664(5) 0.0528(4) 0.0169(5) -0.0121(3) 0.0072(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.362(8) . ? C1 C6 1.381(8) . ? C1 Br1 1.905(5) . ? C2 C3 1.392(7) . ? C2 H2 0.9500 . ? C3 C4 1.387(8) . ? C3 H3 0.9500 . ? C4 C5 1.379(8) . ? C4 C7 1.493(7) . ? C5 C6 1.380(7) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.481(8) . ? C7 C9 1.566(7) . ? C7 H7 1.0000 . ? C8 N1 1.479(7) . ? C8 C9 1.515(8) . ? C8 H8 1.0000 . ? C9 C10 1.487(8) . ? C9 C17 1.513(8) . ? C10 O3 1.207(6) . ? C10 C11 1.489(7) . ? C11 C16 1.381(9) . ? C11 C12 1.390(8) . ? C12 C13 1.390(8) . ? C12 H12 0.9500 . ? C13 C14 1.378(9) . ? C13 H13 0.9500 . ? C14 C15 1.394(9) . ? C14 H14 0.9500 . ? C15 C16 1.386(7) . ? C15 H15 0.9500 . ? C16 C17 1.483(8) . ? C17 O4 1.203(7) . ? N1 O1 1.212(7) . ? N1 O2 1.220(7) . ? 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 C2 C1 C6 121.4(5) . . ? C2 C1 Br1 118.9(4) . . ? C6 C1 Br1 119.6(5) . . ? C1 C2 C3 119.7(5) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 120.0(6) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 118.9(5) . . ? C5 C4 C7 118.1(5) . . ? C3 C4 C7 122.9(5) . . ? C6 C5 C4 121.5(6) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C5 C6 C1 118.5(6) . . ? C5 C6 H6 120.8 . . ? C1 C6 H6 120.8 . . ? C8 C7 C4 124.7(5) . . ? C8 C7 C9 59.6(4) . . ? C4 C7 C9 122.1(5) . . ? C8 C7 H7 113.4 . . ? C4 C7 H7 113.4 . . ? C9 C7 H7 113.4 . . ? N1 C8 C7 118.3(6) . . ? N1 C8 C9 116.7(4) . . ? C7 C8 C9 63.0(4) . . ? N1 C8 H8 116.1 . . ? C7 C8 H8 116.1 . . ? C9 C8 H8 116.1 . . ? C10 C9 C17 108.0(5) . . ? C10 C9 C8 119.9(5) . . ? C17 C9 C8 123.3(5) . . ? C10 C9 C7 121.9(4) . . ? C17 C9 C7 119.0(5) . . ? C8 C9 C7 57.4(3) . . ? O3 C10 C11 127.2(6) . . ? O3 C10 C9 127.3(5) . . ? C11 C10 C9 105.5(5) . . ? C16 C11 C12 122.0(5) . . ? C16 C11 C10 110.8(5) . . ? C12 C11 C10 127.1(6) . . ? C11 C12 C13 116.3(6) . . ? C11 C12 H12 121.9 . . ? C13 C12 H12 121.9 . . ? C14 C13 C12 121.9(7) . . ? C14 C13 H13 119.0 . . ? C12 C13 H13 119.0 . . ? C13 C14 C15 121.5(6) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C16 C15 C14 116.8(6) . . ? C16 C15 H15 121.6 . . ? C14 C15 H15 121.6 . . ? C11 C16 C15 121.5(6) . . ? C11 C16 C17 110.4(5) . . ? C15 C16 C17 128.1(6) . . ? O4 C17 C16 128.1(5) . . ? O4 C17 C9 126.6(5) . . ? C16 C17 C9 105.2(5) . . ? O1 N1 O2 124.2(6) . . ? O1 N1 C8 119.8(5) . . ? O2 N1 C8 116.0(6) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.289 _refine_diff_density_min -0.397 _refine_diff_density_rms 0.078 data_a13901 _database_code_depnum_ccdc_archive 'CCDC 892808' #TrackingRef 'web_deposit_cif_file_2_UtpalDas_1342697118.D451.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H12 Br N O4' _chemical_formula_sum 'C18 H12 Br N O4' _chemical_formula_weight 386.20 _chemical_absolute_configuration ad 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 8.8074(11) _cell_length_b 9.7518(15) _cell_length_c 9.7363(14) _cell_angle_alpha 90.00 _cell_angle_beta 93.785(5) _cell_angle_gamma 90.00 _cell_volume 834.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.69 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 2.484 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2790 _exptl_absorpt_correction_T_max 0.9292 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 5722 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0642 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2477 _reflns_number_gt 1966 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0155P)^2^+0.0595P] 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 0.006(10) _refine_ls_number_reflns 2477 _refine_ls_number_parameters 217 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.0731 _refine_ls_wR_factor_gt 0.0670 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8889(5) 0.0995(4) -0.3740(4) 0.0438(10) Uani 1 1 d . . . C2 C 0.7635(4) 0.1594(5) -0.3236(3) 0.0427(9) Uani 1 1 d . . . H2 H 0.7173 0.2372 -0.3675 0.051 Uiso 1 1 calc R . . C3 C 0.7051(5) 0.1035(4) -0.2064(4) 0.0383(10) Uani 1 1 d . . . H3 H 0.6170 0.1425 -0.1709 0.046 Uiso 1 1 calc R . . C4 C 0.7743(4) -0.0082(3) -0.1414(4) 0.0340(9) Uani 1 1 d . . . C5 C 0.9025(6) -0.0632(4) -0.1943(4) 0.0503(12) Uani 1 1 d . . . H5 H 0.9514 -0.1396 -0.1499 0.060 Uiso 1 1 calc R . . C6 C 0.9604(5) -0.0093(4) -0.3102(4) 0.0547(12) Uani 1 1 d . . . H6 H 1.0492 -0.0474 -0.3455 0.066 Uiso 1 1 calc R . . C7 C 0.7007(5) -0.0753(4) -0.0248(4) 0.0406(10) Uani 1 1 d . . . H7 H 0.6148 -0.1376 -0.0552 0.049 Uiso 1 1 calc R . . C8 C 0.7860(5) -0.1208(4) 0.1030(4) 0.0395(10) Uani 1 1 d . . . C9 C 0.9523(5) -0.1062(4) 0.1378(4) 0.0523(12) Uani 1 1 d . . . H9A H 0.9777 -0.1445 0.2295 0.079 Uiso 1 1 calc R . . H9B H 0.9800 -0.0089 0.1371 0.079 Uiso 1 1 calc R . . H9C H 1.0086 -0.1555 0.0697 0.079 Uiso 1 1 calc R . . C10 C 0.6762(5) 0.0001(3) 0.1091(4) 0.0353(9) Uani 1 1 d . . . C11 C 0.5264(5) -0.0123(4) 0.1769(5) 0.0497(12) Uani 1 1 d . . . C12 C 0.5050(5) 0.1161(4) 0.2526(4) 0.0485(12) Uani 1 1 d . . . C13 C 0.3899(5) 0.1511(6) 0.3393(4) 0.0651(14) Uani 1 1 d . . . H13 H 0.3096 0.0895 0.3558 0.078 Uiso 1 1 calc R . . C14 C 0.3990(8) 0.2806(8) 0.4000(5) 0.085(2) Uani 1 1 d . . . H14 H 0.3252 0.3065 0.4620 0.102 Uiso 1 1 calc R . . C15 C 0.5118(8) 0.3716(6) 0.3725(5) 0.0743(18) Uani 1 1 d . . . H15 H 0.5128 0.4601 0.4134 0.089 Uiso 1 1 calc R . . C16 C 0.6228(6) 0.3369(5) 0.2870(5) 0.0550(12) Uani 1 1 d . . . H16 H 0.7002 0.4005 0.2676 0.066 Uiso 1 1 calc R . . C17 C 0.6197(5) 0.2077(4) 0.2297(4) 0.0392(11) Uani 1 1 d . . . C18 C 0.7321(5) 0.1433(4) 0.1408(3) 0.0362(10) Uani 1 1 d . . . N1 N 0.7259(5) -0.2520(4) 0.1636(4) 0.0563(11) Uani 1 1 d . . . O1 O 0.6845(4) -0.3431(4) 0.0850(3) 0.0838(10) Uani 1 1 d . . . O2 O 0.7297(5) -0.2598(3) 0.2874(4) 0.0802(12) Uani 1 1 d . . . O3 O 0.4432(4) -0.1103(3) 0.1669(4) 0.0866(13) Uani 1 1 d . . . O4 O 0.8464(3) 0.1960(3) 0.1022(2) 0.0482(7) Uani 1 1 d . . . Br1 Br 0.96743(5) 0.16995(7) -0.53772(4) 0.0737(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.044(3) 0.055(3) 0.032(2) 0.0001(19) -0.0005(19) 0.001(2) C2 0.044(2) 0.038(2) 0.045(2) 0.006(2) -0.0047(18) 0.008(2) C3 0.038(3) 0.037(2) 0.040(2) -0.0028(17) 0.0015(19) 0.0085(17) C4 0.037(3) 0.030(2) 0.034(2) 0.0009(17) -0.0041(18) 0.0054(18) C5 0.062(4) 0.046(2) 0.042(3) 0.001(2) -0.002(2) 0.019(2) C6 0.049(3) 0.070(3) 0.046(3) -0.009(2) 0.003(2) 0.027(2) C7 0.042(3) 0.033(2) 0.046(3) -0.0020(18) -0.007(2) -0.0006(18) C8 0.044(3) 0.034(2) 0.041(2) 0.0014(18) 0.002(2) 0.000(2) C9 0.048(3) 0.067(3) 0.040(2) -0.002(2) -0.012(2) 0.015(2) C10 0.031(2) 0.031(2) 0.043(2) -0.0014(18) 0.0040(18) -0.0016(17) C11 0.051(3) 0.038(3) 0.061(3) 0.021(2) 0.013(2) -0.001(2) C12 0.047(3) 0.057(3) 0.043(2) 0.0175(19) 0.013(2) 0.010(2) C13 0.055(3) 0.086(4) 0.056(3) 0.031(3) 0.021(2) 0.024(3) C14 0.093(6) 0.128(6) 0.036(3) 0.002(3) 0.009(3) 0.065(5) C15 0.088(5) 0.082(4) 0.049(3) -0.020(3) -0.025(3) 0.048(4) C16 0.058(4) 0.054(3) 0.050(3) -0.015(2) -0.018(3) 0.012(2) C17 0.041(3) 0.045(3) 0.0306(19) 0.0055(18) -0.0057(18) 0.008(2) C18 0.038(3) 0.038(3) 0.0314(18) 0.0024(17) -0.0023(17) -0.002(2) N1 0.072(3) 0.042(2) 0.056(3) 0.012(2) 0.007(2) 0.004(2) O1 0.131(3) 0.0392(18) 0.081(2) 0.006(2) 0.007(2) -0.016(3) O2 0.117(4) 0.067(2) 0.058(2) 0.0204(17) 0.014(2) 0.0078(19) O3 0.062(3) 0.052(2) 0.149(4) 0.018(2) 0.036(2) -0.0182(18) O4 0.0430(17) 0.053(2) 0.0487(14) -0.0047(15) 0.0053(13) -0.0178(16) Br1 0.0605(3) 0.1159(4) 0.0451(2) 0.0176(4) 0.0066(2) 0.0029(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.362(6) . ? C1 C2 1.369(5) . ? C1 Br1 1.907(4) . ? C2 C3 1.393(5) . ? C2 H2 0.9500 . ? C3 C4 1.380(5) . ? C3 H3 0.9500 . ? C4 C5 1.380(5) . ? C4 C7 1.495(5) . ? C5 C6 1.373(6) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.479(5) . ? C7 C10 1.524(5) . ? C7 H7 1.0000 . ? C8 C9 1.488(6) . ? C8 N1 1.519(5) . ? C8 C10 1.529(5) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C18 1.506(5) . ? C10 C11 1.519(6) . ? C11 O3 1.205(5) . ? C11 C12 1.471(6) . ? C12 C17 1.378(5) . ? C12 C13 1.403(6) . ? C13 C14 1.395(8) . ? C13 H13 0.9500 . ? C14 C15 1.372(8) . ? C14 H14 0.9500 . ? C15 C16 1.368(7) . ? C15 H15 0.9500 . ? C16 C17 1.378(6) . ? C16 H16 0.9500 . ? C17 C18 1.495(5) . ? C18 O4 1.212(4) . ? N1 O2 1.206(4) . ? N1 O1 1.213(5) . ? 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 C6 C1 C2 121.9(4) . . ? C6 C1 Br1 118.6(3) . . ? C2 C1 Br1 119.5(3) . . ? C1 C2 C3 118.5(4) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C4 C3 C2 120.6(4) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 118.9(3) . . ? C3 C4 C7 119.5(3) . . ? C5 C4 C7 121.3(3) . . ? C6 C5 C4 121.0(4) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C1 C6 C5 119.2(4) . . ? C1 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C8 C7 C4 123.3(4) . . ? C8 C7 C10 61.2(3) . . ? C4 C7 C10 122.1(3) . . ? C8 C7 H7 113.5 . . ? C4 C7 H7 113.5 . . ? C10 C7 H7 113.5 . . ? C7 C8 C9 126.9(3) . . ? C7 C8 N1 114.1(3) . . ? C9 C8 N1 110.8(3) . . ? C7 C8 C10 60.9(3) . . ? C9 C8 C10 122.2(3) . . ? N1 C8 C10 113.4(3) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C18 C10 C11 105.4(3) . . ? C18 C10 C7 124.1(3) . . ? C11 C10 C7 120.7(4) . . ? C18 C10 C8 121.6(3) . . ? C11 C10 C8 121.7(3) . . ? C7 C10 C8 57.9(2) . . ? O3 C11 C12 128.2(4) . . ? O3 C11 C10 124.7(4) . . ? C12 C11 C10 107.1(4) . . ? C17 C12 C13 120.4(4) . . ? C17 C12 C11 110.5(3) . . ? C13 C12 C11 129.1(4) . . ? C14 C13 C12 116.9(5) . . ? C14 C13 H13 121.6 . . ? C12 C13 H13 121.6 . . ? C15 C14 C13 121.7(5) . . ? C15 C14 H14 119.2 . . ? C13 C14 H14 119.2 . . ? C16 C15 C14 121.0(5) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C17 118.5(5) . . ? C15 C16 H16 120.7 . . ? C17 C16 H16 120.7 . . ? C12 C17 C16 121.5(4) . . ? C12 C17 C18 110.0(3) . . ? C16 C17 C18 128.5(4) . . ? O4 C18 C17 126.6(4) . . ? O4 C18 C10 126.6(3) . . ? C17 C18 C10 106.7(3) . . ? O2 N1 O1 124.9(4) . . ? O2 N1 C8 117.0(4) . . ? O1 N1 C8 118.0(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.286 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.046