# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'RSC Advances' _journal_coden_cambridge 1500 #TrackingRef '2d1B.cif' #===================================================================== # SUBMISSION DETAILS _publ_contact_letter ; This is a file we would like to deposit with the CCDC. Corresponding publication is on the way. Best regards, Thierry Prange ; _publ_contact_author_name 'Prof. Thierry Prange' _publ_contact_author_address ; Laboratoire de cristallographie et RMN Biologique (UMR 8015-CNRS), 4 Av. de l'Observatoire, 75006 Paris, France ; _publ_contact_author_email thierry.prange@parisdescartes.fr _publ_contact_author_fax '33 1 53 73 96 63' _publ_contact_author_phone '33 1 53 73 99 25' _publ_section_title ; Naphthalene-dioxygenase catalysed cis-dihydroxylation of azaarenes: quinoline, isoquinoline and C-methyl derivatives ; _publ_section_title_footnote ; ? ; loop_ _publ_author_name _publ_author_footnote _publ_author_address C.Chopard . ; Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques (UMR CNRS 8601), 45 rue des Saints Peres, 75270 Paris cedex 06, France ; T.Prange . ; Laboratoire de Cristallographie et RMN Biologiques (UMR 8015-CNRS), 4 Ave de l'Observatoire 75270 Paris Cedex 6, France ; _publ_section_details ; Some "Alert A"s remain (resolution too low, etc... ) They are due to geometric limitations of the CCD detector we used ; #=============================================================== #== begin of cif file =========================================== #=============================================================== data_2D1B _database_code_depnum_ccdc_archive 'CCDC 815425' #TrackingRef '2d1B.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-bromophenylboronate derivative of [5R,6S]-2-methyl-5,6-dihydroquinoline-5,6-diol ; _chemical_name_common ; 2D1B ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H13 B Br N O2' _chemical_formula_weight 341.78 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 '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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 4.320(4) _cell_length_b 10.637(4) _cell_length_c 16.090(4) _cell_angle_alpha 90.000(5) _cell_angle_beta 94.110(5) _cell_angle_gamma 90.000(5) _cell_volume 737.5(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.540 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 2.789 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Brucker KAPPA CCD' _diffrn_measurement_method rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1500 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3017 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0542 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 21.96 _reflns_number_total 1799 _reflns_number_gt 1495 _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^)+(0.0259P)^2^+0.3076P] 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 0.064(14) _refine_ls_number_reflns 1799 _refine_ls_number_parameters 190 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0866 _refine_ls_wR_factor_gt 0.0802 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.019 _refine_ls_shift/su_mean 0.004 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 -0.18653(16) 0.27923(9) -0.25345(4) 0.0918(3) Uani 1 1 d . . . B1 B 0.4754(12) 0.2868(11) 0.1031(4) 0.0582(17) Uani 1 1 d . . . O1 O 0.4650(9) 0.1967(4) 0.1618(2) 0.0642(10) Uani 1 1 d . . . O2 O 0.6627(10) 0.3873(4) 0.1264(3) 0.0747(12) Uani 1 1 d . . . C11 C 0.3012(10) 0.2863(8) 0.0156(3) 0.0551(13) Uani 1 1 d . . . C12 C 0.3236(16) 0.3859(6) -0.0390(5) 0.0720(19) Uani 1 1 d . . . H12 H 0.4404 0.4557 -0.0216 0.086 Uiso 1 1 calc R . . C13 C 0.1810(18) 0.3853(6) -0.1173(5) 0.0736(19) Uani 1 1 d . . . H13 H 0.2024 0.4532 -0.1528 0.088 Uiso 1 1 calc R . . C14 C 0.0059(11) 0.2835(9) -0.1428(3) 0.0599(13) Uani 1 1 d . . . C15 C -0.0286(15) 0.1819(6) -0.0920(4) 0.0641(16) Uani 1 1 d . . . H15 H -0.1477 0.1130 -0.1101 0.077 Uiso 1 1 calc R . . C16 C 0.1212(14) 0.1851(6) -0.0119(4) 0.0607(16) Uani 1 1 d . . . H16 H 0.0991 0.1173 0.0237 0.073 Uiso 1 1 calc R . . C1 C 0.6806(14) 0.2332(6) 0.2329(4) 0.066(2) Uani 1 1 d . . . H1 H 0.8644 0.1790 0.2336 0.079 Uiso 1 1 calc R . . C2 C 0.7748(15) 0.3663(7) 0.2117(5) 0.068(2) Uani 1 1 d . . . H2 H 1.0019 0.3714 0.2156 0.082 Uiso 1 1 calc R . . C3 C 0.6513(14) 0.4677(6) 0.2649(4) 0.0697(18) Uani 1 1 d . . . H3 H 0.6832 0.5512 0.2505 0.084 Uiso 1 1 calc R . . C4 C 0.4975(16) 0.4429(7) 0.3319(5) 0.073(2) Uani 1 1 d . . . H4 H 0.4268 0.5099 0.3625 0.087 Uiso 1 1 calc R . . C5 C 0.4359(13) 0.3165(5) 0.3592(4) 0.0578(18) Uani 1 1 d . . . N6 N 0.2871(12) 0.3027(7) 0.4292(4) 0.0757(18) Uani 1 1 d . . . C7 C 0.2295(17) 0.1902(9) 0.4551(5) 0.076(2) Uani 1 1 d . . . C8 C 0.3151(17) 0.0847(8) 0.4142(5) 0.089(2) Uani 1 1 d . . . H8 H 0.2717 0.0054 0.4348 0.106 Uiso 1 1 calc R . . C9 C 0.4673(19) 0.0968(8) 0.3416(6) 0.081(2) Uani 1 1 d . . . H9 H 0.5287 0.0260 0.3131 0.097 Uiso 1 1 calc R . . C10 C 0.5250(13) 0.2140(6) 0.3128(4) 0.0619(17) Uani 1 1 d . . . C7M C 0.0588(19) 0.1826(9) 0.5352(4) 0.119(3) Uani 1 1 d . . . H7A H 0.0283 0.0960 0.5494 0.154 Uiso 1 1 calc R . . H7B H -0.1389 0.2236 0.5268 0.154 Uiso 1 1 calc R . . H7C H 0.1802 0.2233 0.5797 0.154 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 0.1169(5) 0.0925(5) 0.0654(4) 0.0019(6) 0.0019(3) 0.0208(6) B1 0.037(3) 0.063(5) 0.076(5) -0.015(7) 0.020(3) 0.001(5) O1 0.068(3) 0.058(3) 0.066(3) -0.004(2) -0.002(2) -0.006(2) O2 0.080(3) 0.081(3) 0.065(3) -0.007(2) 0.014(2) -0.022(3) C11 0.051(3) 0.050(4) 0.067(3) -0.011(5) 0.021(3) -0.001(4) C12 0.095(5) 0.053(4) 0.072(5) -0.014(4) 0.027(4) -0.016(4) C13 0.102(5) 0.053(4) 0.068(5) 0.004(4) 0.022(4) 0.000(4) C14 0.074(3) 0.060(4) 0.046(3) -0.004(5) 0.008(2) 0.013(5) C15 0.070(4) 0.055(4) 0.067(5) -0.002(4) 0.007(4) 0.006(3) C16 0.071(4) 0.048(4) 0.066(4) 0.002(3) 0.019(4) 0.007(3) C1 0.051(4) 0.079(6) 0.067(4) -0.015(3) 0.000(3) 0.003(3) C2 0.049(4) 0.076(5) 0.081(5) -0.013(4) 0.011(4) -0.009(3) C3 0.074(4) 0.053(4) 0.081(5) -0.019(4) 0.003(4) -0.015(3) C4 0.071(5) 0.071(6) 0.076(6) -0.023(4) 0.008(5) -0.006(4) C5 0.057(3) 0.058(5) 0.057(4) -0.004(3) -0.008(3) -0.005(3) N6 0.067(3) 0.098(6) 0.062(4) 0.002(4) 0.002(3) 0.004(4) C7 0.075(4) 0.084(6) 0.068(5) 0.012(5) -0.011(4) 0.001(4) C8 0.098(5) 0.073(5) 0.093(6) 0.026(5) -0.002(5) -0.010(4) C9 0.100(6) 0.055(5) 0.086(7) -0.002(4) -0.003(5) -0.001(4) C10 0.051(3) 0.064(5) 0.068(5) -0.005(4) -0.010(3) 0.008(3) C7M 0.100(5) 0.168(8) 0.089(5) 0.052(6) 0.015(5) -0.004(6) _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 C14 1.911(5) . ? B1 O1 1.349(9) . ? B1 O2 1.376(10) . ? B1 C11 1.547(8) . ? O1 C1 1.474(7) . ? O2 C2 1.439(9) . ? C11 C16 1.382(10) . ? C11 C12 1.384(10) . ? C12 C13 1.362(9) . ? C13 C14 1.367(10) . ? C14 C15 1.369(9) . ? C15 C16 1.400(8) . ? C1 C10 1.507(8) . ? C1 C2 1.519(9) . ? C2 C3 1.498(9) . ? C3 C4 1.333(10) . ? C4 C5 1.445(10) . ? C5 N6 1.345(8) . ? C5 C10 1.391(7) . ? N6 C7 1.296(10) . ? C7 C8 1.365(11) . ? C7 C7M 1.533(10) . ? C8 C9 1.387(11) . ? C9 C10 1.359(10) . ? 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 O1 B1 O2 114.2(5) . . ? O1 B1 C11 126.5(7) . . ? O2 B1 C11 119.3(8) . . ? B1 O1 C1 107.8(5) . . ? B1 O2 C2 106.9(5) . . ? C16 C11 C12 117.1(5) . . ? C16 C11 B1 121.3(7) . . ? C12 C11 B1 121.5(7) . . ? C13 C12 C11 122.4(6) . . ? C12 C13 C14 119.0(6) . . ? C13 C14 C15 121.9(5) . . ? C13 C14 Br1 119.5(6) . . ? C15 C14 Br1 118.6(6) . . ? C14 C15 C16 117.8(6) . . ? C11 C16 C15 121.7(6) . . ? O1 C1 C10 109.3(5) . . ? O1 C1 C2 103.7(6) . . ? C10 C1 C2 117.4(5) . . ? O2 C2 C3 108.9(6) . . ? O2 C2 C1 106.3(6) . . ? C3 C2 C1 115.5(5) . . ? C4 C3 C2 122.5(7) . . ? C3 C4 C5 122.9(7) . . ? N6 C5 C10 122.1(6) . . ? N6 C5 C4 117.8(6) . . ? C10 C5 C4 120.1(6) . . ? C7 N6 C5 118.9(7) . . ? N6 C7 C8 122.7(7) . . ? N6 C7 C7M 115.7(8) . . ? C8 C7 C7M 121.6(8) . . ? C7 C8 C9 119.3(7) . . ? C10 C9 C8 118.9(8) . . ? C9 C10 C5 118.1(6) . . ? C9 C10 C1 121.3(7) . . ? C5 C10 C1 120.7(6) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 21.96 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.173 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.045 # Attachment '7d2B.cif' data_claude7d2B _database_code_depnum_ccdc_archive 'CCDC 815426' #TrackingRef '7d2B.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-bromophenylboronate derivative of [7S,8R]-1-methyl- 7,8-dihydroisoquinoline-7,8-diol ; _chemical_name_common 7d2B _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H13 B Br N1 O2' _chemical_formula_weight 341.98 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 '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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.683(2) _cell_length_b 4.267(2) _cell_length_c 14.339(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.93(5) _cell_angle_gamma 90.00 _cell_volume 738.3(4) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 5.562 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.92000 _diffrn_radiation_type ? _diffrn_radiation_source synchrotron _diffrn_radiation_monochromator Si(111) _diffrn_measurement_device_type 'ADSC Quantum' _diffrn_measurement_method rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1500 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 1632 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0154 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 28.03 _reflns_number_total 1632 _reflns_number_gt 1629 _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^)+(0.1000P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.027(12) _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 0.02(20) _refine_ls_number_reflns 1632 _refine_ls_number_parameters 188 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0830 _refine_ls_R_factor_gt 0.0829 _refine_ls_wR_factor_ref 0.2514 _refine_ls_wR_factor_gt 0.2513 _refine_ls_goodness_of_fit_ref 2.689 _refine_ls_restrained_S_all 2.688 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.068 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 0.48079(9) 0.0729(4) 0.68101(8) 0.0938(9) Uani 1 1 d . . . C1 C 0.6108(5) -0.1264(18) 0.6799(5) 0.0318(18) Uani 1 1 d . . . C2 C 0.6864(7) -0.231(2) 0.7673(5) 0.047(2) Uani 1 1 d . . . H2 H 0.6730 -0.1998 0.8268 0.056 Uiso 1 1 calc R . . C3 C 0.7818(6) -0.382(2) 0.7639(5) 0.048(2) Uani 1 1 d . . . H3 H 0.8310 -0.4560 0.8222 0.057 Uiso 1 1 calc R . . C4 C 0.8071(5) -0.4288(16) 0.6779(4) 0.0212(14) Uani 1 1 d . . . C5 C 0.7317(6) -0.3182(17) 0.5914(5) 0.0339(19) Uani 1 1 d . . . H5 H 0.7470 -0.3494 0.5327 0.041 Uiso 1 1 calc R . . C6 C 0.6385(7) -0.1693(19) 0.5895(5) 0.042(2) Uani 1 1 d . . . H6 H 0.5914 -0.0932 0.5306 0.050 Uiso 1 1 calc R . . B1 B 0.9150(7) -0.6077(18) 0.6803(5) 0.030(2) Uani 1 1 d . . . O1 O 0.9823(4) -0.7251(11) 0.7654(3) 0.0309(13) Uani 1 1 d . . . O2 O 0.9506(4) -0.6520(12) 0.6030(3) 0.0348(12) Uani 1 1 d . . . C1A C 1.0711(6) -0.8935(15) 0.7437(4) 0.0282(17) Uani 1 1 d . . . H1A H 1.0599 -1.1189 0.7496 0.034 Uiso 1 1 calc . . . C2A C 1.0589(6) -0.816(2) 0.6359(5) 0.0377(19) Uani 1 1 d . . . H2A H 1.0550 -1.0106 0.5985 0.045 Uiso 1 1 calc . . . C3A C 1.1431(6) -0.6112(19) 0.6200(5) 0.0331(18) Uani 1 1 d . . . H3A H 1.1307 -0.5308 0.5573 0.040 Uiso 1 1 calc R . . C4A C 1.2360(6) -0.5296(19) 0.6876(5) 0.0371(19) Uani 1 1 d . . . H4A H 1.2872 -0.4048 0.6704 0.044 Uiso 1 1 calc R . . C5A C 1.2590(6) -0.6334(17) 0.7889(4) 0.0263(16) Uani 1 1 d . . . C6A C 1.3544(7) -0.548(2) 0.8593(7) 0.053(3) Uani 1 1 d . . . H6A H 1.4086 -0.4316 0.8436 0.063 Uiso 1 1 calc R . . C7A C 1.3680(8) -0.641(2) 0.9557(6) 0.054(2) Uani 1 1 d . . . H7A H 1.4328 -0.5816 1.0036 0.065 Uiso 1 1 calc R . . N8A N 1.2969(6) -0.8040(17) 0.9828(4) 0.0455(18) Uani 1 1 d . . . C9A C 1.2026(7) -0.8892(16) 0.9177(4) 0.0362(18) Uani 1 1 d . . . C10A C 1.1814(6) -0.8009(15) 0.8160(4) 0.0267(16) Uani 1 1 d . . . C11A C 1.1216(8) -1.075(2) 0.9512(5) 0.052(2) Uani 1 1 d . . . H11A H 1.0573 -1.1175 0.8964 0.068 Uiso 1 1 calc R . . H11B H 1.1004 -0.9584 0.9998 0.068 Uiso 1 1 calc R . . H11C H 1.1551 -1.2693 0.9790 0.068 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 0.0721(12) 0.1012(12) 0.1163(13) 0.0060(8) 0.0410(8) 0.0117(7) C1 0.015(4) 0.049(4) 0.031(4) -0.006(4) 0.007(3) -0.001(3) C2 0.037(5) 0.086(6) 0.019(3) -0.001(4) 0.011(3) 0.006(5) C3 0.023(4) 0.083(6) 0.026(4) -0.007(4) -0.009(3) 0.009(5) C4 0.011(3) 0.034(3) 0.016(3) -0.005(3) 0.001(2) -0.004(3) C5 0.024(4) 0.052(4) 0.022(4) 0.001(3) 0.003(3) 0.006(3) C6 0.052(5) 0.056(4) 0.021(4) 0.008(3) 0.016(3) 0.003(4) B1 0.039(5) 0.031(4) 0.014(4) -0.005(3) -0.001(3) -0.022(4) O1 0.019(3) 0.049(3) 0.018(2) 0.003(2) -0.006(2) 0.005(2) O2 0.019(2) 0.059(3) 0.018 -0.005(2) -0.0070(18) 0.014(2) C1A 0.027(4) 0.028(3) 0.020(3) -0.008(3) -0.007(3) 0.002(3) C2A 0.029(4) 0.059(5) 0.020(3) -0.013(3) -0.001(3) 0.017(4) C3A 0.024(4) 0.055(4) 0.022(4) 0.005(3) 0.010(3) 0.016(4) C4A 0.019(4) 0.053(4) 0.048(4) 0.002(3) 0.022(4) 0.006(3) C5A 0.018(4) 0.044(3) 0.011(3) -0.005(3) -0.004(3) 0.012(3) C6A 0.026(4) 0.066(6) 0.065(6) -0.016(4) 0.014(4) 0.010(4) C7A 0.048(5) 0.063(6) 0.039(5) -0.011(4) -0.007(4) 0.010(5) N8A 0.043(4) 0.056(4) 0.021 -0.012(3) -0.013(3) 0.011 C9A 0.057(5) 0.036(4) 0.009(3) -0.003(3) 0.000(3) 0.015(4) C10A 0.035(4) 0.032(3) 0.006(3) -0.008(3) -0.002(3) 0.014(3) C11A 0.072(6) 0.056(4) 0.026(4) 0.007(4) 0.011(4) -0.004(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 Br1 C1 1.859(7) . ? C1 C2 1.397(12) . ? C1 C6 1.455(10) . ? C2 C3 1.385(11) . ? C3 C4 1.380(9) . ? C4 C5 1.395(10) . ? C4 B1 1.559(11) . ? C5 C6 1.335(11) . ? B1 O2 1.331(9) . ? B1 O1 1.352(9) . ? O1 C1A 1.449(8) . ? O2 C2A 1.484(9) . ? C1A C10A 1.514(10) . ? C1A C2A 1.541(9) . ? C2A C3A 1.452(12) . ? C3A C4A 1.320(11) . ? C4A C5A 1.459(10) . ? C5A C10A 1.366(11) . ? C5A C6A 1.365(12) . ? C6A C7A 1.396(13) . ? C7A N8A 1.290(12) . ? N8A C9A 1.321(11) . ? C9A C10A 1.449(9) . ? C9A C11A 1.490(12) . ? 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 118.1(7) . . ? C2 C1 Br1 120.3(5) . . ? C6 C1 Br1 121.5(5) . . ? C3 C2 C1 118.9(6) . . ? C4 C3 C2 122.9(6) . . ? C3 C4 C5 117.5(6) . . ? C3 C4 B1 119.7(5) . . ? C5 C4 B1 122.8(5) . . ? C6 C5 C4 122.6(6) . . ? C5 C6 C1 119.8(6) . . ? O2 B1 O1 114.7(7) . . ? O2 B1 C4 124.9(6) . . ? O1 B1 C4 120.4(6) . . ? B1 O1 C1A 107.8(5) . . ? B1 O2 C2A 108.7(5) . . ? O1 C1A C10A 109.8(4) . . ? O1 C1A C2A 105.4(5) . . ? C10A C1A C2A 114.7(6) . . ? C3A C2A O2 108.6(7) . . ? C3A C2A C1A 115.7(6) . . ? O2 C2A C1A 102.5(5) . . ? C4A C3A C2A 125.2(6) . . ? C3A C4A C5A 120.7(7) . . ? C10A C5A C6A 118.7(7) . . ? C10A C5A C4A 120.1(6) . . ? C6A C5A C4A 121.0(8) . . ? C5A C6A C7A 117.9(9) . . ? N8A C7A C6A 124.5(8) . . ? C7A N8A C9A 120.0(6) . . ? N8A C9A C10A 119.1(7) . . ? N8A C9A C11A 118.8(6) . . ? C10A C9A C11A 122.0(7) . . ? C5A C10A C9A 119.7(6) . . ? C5A C10A C1A 122.4(5) . . ? C9A C10A C1A 117.9(6) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 28.03 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.881 _refine_diff_density_min -0.683 _refine_diff_density_rms 0.147