# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Blake, A.' 'Lera, Manuel' 'Mascal, Mark' 'Wilson, Claire' _publ_contact_author_name 'Prof Mark Mascal' _publ_contact_author_address ; Chemistry and Biochemistry UCLA 405 Hilgard Ave. Los Angeles California 90095 UNITED STATES OF AMERICA ; _publ_contact_author_email 'MASCAL@CHEM.UCLA.EDU' _publ_section_title ; Azatriquinanes. 4. The Chemistry of Azatriquinenamine and its Bromination Products ; data_compound_7 _database_code_CSD 170513 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H14 Br N O' _chemical_formula_weight 232.12 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.5959(6) _cell_length_b 11.2333(10) _cell_length_c 10.9437(9) _cell_angle_alpha 90.00 _cell_angle_beta 99.459(2) _cell_angle_gamma 90.00 _cell_volume 921.10(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2891 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 28.74 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.674 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 4.414 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.407 _exptl_absorpt_correction_T_max 0.545 _exptl_absorpt_process_details 'SADABS, Bruker' _exptl_special_details ? _diffrn_ambient_temperature 150(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 'Bruker SMART CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'less than 1' _diffrn_reflns_number 5917 _diffrn_reflns_av_R_equivalents 0.028 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 28.95 _reflns_number_total 2170 _reflns_number_gt 1752 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0464P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment 'riding model, OH rigid rotating group' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2170 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0397 _refine_ls_R_factor_gt 0.0289 _refine_ls_wR_factor_ref 0.0731 _refine_ls_wR_factor_gt 0.0700 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.973 _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 Br Br 1.12995(3) 0.51986(2) 0.23286(2) 0.03275(10) Uani 1 1 d . . . O O 0.8160(2) 0.54952(14) 0.37384(15) 0.0247(4) Uani 1 1 d . . . H1A H 0.9079 0.5681 0.4239 0.037 Uiso 1 1 calc R . . N N 0.9246(2) 0.35593(16) 0.43956(15) 0.0193(4) Uani 1 1 d . . . C1 C 0.8284(3) 0.4303(2) 0.33800(19) 0.0212(4) Uani 1 1 d . . . C2 C 0.9277(3) 0.4096(2) 0.2283(2) 0.0240(5) Uani 1 1 d . . . H2A H 0.8440 0.4170 0.1480 0.036 Uiso 1 1 calc R . . C3 C 0.9965(3) 0.2830(2) 0.2468(2) 0.0262(5) Uani 1 1 d . . . H3A H 1.1010 0.2701 0.2051 0.039 Uiso 1 1 calc R . . H3B H 0.9024 0.2247 0.2150 0.039 Uiso 1 1 calc R . . C4 C 1.0485(3) 0.2737(2) 0.3877(2) 0.0232(5) Uani 1 1 d . . . H4 H 1.1753 0.2987 0.4144 0.035 Uiso 1 1 calc R . . C5 C 1.0157(3) 0.1517(2) 0.4408(2) 0.0277(5) Uani 1 1 d . . . H5A H 1.0424 0.0873 0.3850 0.041 Uiso 1 1 calc R . . H5B H 1.0894 0.1404 0.5233 0.041 Uiso 1 1 calc R . . C6 C 0.8187(3) 0.1544(2) 0.4498(2) 0.0271(5) Uani 1 1 d . . . H6A H 0.7900 0.0958 0.5112 0.041 Uiso 1 1 calc R . . H6B H 0.7444 0.1378 0.3685 0.041 Uiso 1 1 calc R . . C7 C 0.7910(3) 0.2820(2) 0.4920(2) 0.0232(5) Uani 1 1 d . . . H7 H 0.8138 0.2866 0.5846 0.035 Uiso 1 1 calc R . . C8 C 0.6108(3) 0.3372(2) 0.4412(2) 0.0280(5) Uani 1 1 d . . . H8A H 0.5831 0.4042 0.4937 0.042 Uiso 1 1 calc R . . H8B H 0.5140 0.2774 0.4352 0.042 Uiso 1 1 calc R . . C9 C 0.6369(3) 0.3807(2) 0.3128(2) 0.0254(5) Uani 1 1 d . . . H9A H 0.5496 0.4435 0.2816 0.038 Uiso 1 1 calc R . . H9B H 0.6262 0.3144 0.2525 0.038 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 Br 0.03052(15) 0.03339(16) 0.03733(16) -0.00456(11) 0.01439(10) -0.00821(11) O 0.0250(8) 0.0194(9) 0.0286(8) -0.0024(7) 0.0009(6) 0.0035(6) N 0.0190(8) 0.0195(10) 0.0194(9) -0.0002(7) 0.0035(7) 0.0026(7) C1 0.0201(10) 0.0200(11) 0.0232(11) -0.0006(9) 0.0023(8) 0.0021(9) C2 0.0238(10) 0.0268(13) 0.0219(11) -0.0014(9) 0.0050(9) -0.0039(9) C3 0.0294(11) 0.0262(13) 0.0246(11) -0.0049(10) 0.0094(9) 0.0004(10) C4 0.0213(10) 0.0223(12) 0.0261(11) -0.0041(9) 0.0045(8) 0.0062(9) C5 0.0338(12) 0.0214(13) 0.0272(12) -0.0009(10) 0.0033(9) 0.0084(10) C6 0.0340(12) 0.0218(13) 0.0259(12) 0.0024(10) 0.0063(9) -0.0006(10) C7 0.0241(10) 0.0229(12) 0.0237(11) 0.0000(9) 0.0074(8) -0.0001(9) C8 0.0236(11) 0.0280(13) 0.0338(13) 0.0011(10) 0.0094(9) -0.0003(10) C9 0.0181(10) 0.0271(13) 0.0300(12) 0.0013(10) 0.0010(9) -0.0002(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 Br C2 1.968(2) . ? O C1 1.404(3) . ? O H1A 0.8400 . ? N C1 1.483(3) . ? N C4 1.495(3) . ? N C7 1.497(3) . ? C1 C2 1.537(3) . ? C1 C9 1.539(3) . ? C2 C3 1.516(3) . ? C2 H2A 1.0000 . ? C3 C4 1.531(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.524(3) . ? C4 H4 1.0000 . ? C5 C6 1.516(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.531(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.522(3) . ? C7 H7 1.0000 . ? C8 C9 1.531(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? 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 O H1A 109.5 . . ? C1 N C4 109.08(16) . . ? C1 N C7 108.54(15) . . ? C4 N C7 108.13(16) . . ? O C1 N 112.04(17) . . ? O C1 C2 115.25(18) . . ? N C1 C2 104.80(17) . . ? O C1 C9 106.90(17) . . ? N C1 C9 105.39(17) . . ? C2 C1 C9 112.09(17) . . ? C3 C2 C1 103.87(18) . . ? C3 C2 Br 109.67(15) . . ? C1 C2 Br 111.49(15) . . ? C3 C2 H2A 110.5 . . ? C1 C2 H2A 110.5 . . ? Br C2 H2A 110.5 . . ? C2 C3 C4 103.02(17) . . ? C2 C3 H3A 111.2 . . ? C4 C3 H3A 111.2 . . ? C2 C3 H3B 111.2 . . ? C4 C3 H3B 111.2 . . ? H3A C3 H3B 109.1 . . ? N C4 C5 104.98(17) . . ? N C4 C3 105.39(17) . . ? C5 C4 C3 114.46(19) . . ? N C4 H4 110.6 . . ? C5 C4 H4 110.6 . . ? C3 C4 H4 110.6 . . ? C6 C5 C4 103.41(19) . . ? C6 C5 H5A 111.1 . . ? C4 C5 H5A 111.1 . . ? C6 C5 H5B 111.1 . . ? C4 C5 H5B 111.1 . . ? H5A C5 H5B 109.0 . . ? C5 C6 C7 102.97(19) . . ? C5 C6 H6A 111.2 . . ? C7 C6 H6A 111.2 . . ? C5 C6 H6B 111.2 . . ? C7 C6 H6B 111.2 . . ? H6A C6 H6B 109.1 . . ? N C7 C8 105.04(17) . . ? N C7 C6 105.53(17) . . ? C8 C7 C6 115.54(19) . . ? N C7 H7 110.1 . . ? C8 C7 H7 110.1 . . ? C6 C7 H7 110.1 . . ? C7 C8 C9 102.76(17) . . ? C7 C8 H8A 111.2 . . ? C9 C8 H8A 111.2 . . ? C7 C8 H8B 111.2 . . ? C9 C8 H8B 111.2 . . ? H8A C8 H8B 109.1 . . ? C8 C9 C1 102.25(17) . . ? C8 C9 H9A 111.3 . . ? C1 C9 H9A 111.3 . . ? C8 C9 H9B 111.3 . . ? C1 C9 H9B 111.3 . . ? H9A C9 H9B 109.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N C1 O -137.75(17) . . . . ? C7 N C1 O 104.65(19) . . . . ? C4 N C1 C2 -12.1(2) . . . . ? C7 N C1 C2 -129.69(17) . . . . ? C4 N C1 C9 106.35(19) . . . . ? C7 N C1 C9 -11.2(2) . . . . ? O C1 C2 C3 154.51(17) . . . . ? N C1 C2 C3 30.9(2) . . . . ? C9 C1 C2 C3 -82.9(2) . . . . ? O C1 C2 Br 36.5(2) . . . . ? N C1 C2 Br -87.15(18) . . . . ? C9 C1 C2 Br 159.06(16) . . . . ? C1 C2 C3 C4 -37.4(2) . . . . ? Br C2 C3 C4 81.90(17) . . . . ? C1 N C4 C5 -132.40(18) . . . . ? C7 N C4 C5 -14.5(2) . . . . ? C1 N C4 C3 -11.2(2) . . . . ? C7 N C4 C3 106.67(18) . . . . ? C2 C3 C4 N 30.1(2) . . . . ? C2 C3 C4 C5 144.94(19) . . . . ? N C4 C5 C6 33.2(2) . . . . ? C3 C4 C5 C6 -81.8(2) . . . . ? C4 C5 C6 C7 -38.8(2) . . . . ? C1 N C7 C8 -14.0(2) . . . . ? C4 N C7 C8 -132.19(17) . . . . ? C1 N C7 C6 108.56(19) . . . . ? C4 N C7 C6 -9.6(2) . . . . ? C5 C6 C7 N 30.0(2) . . . . ? C5 C6 C7 C8 145.58(19) . . . . ? N C7 C8 C9 33.6(2) . . . . ? C6 C7 C8 C9 -82.2(2) . . . . ? C7 C8 C9 C1 -39.9(2) . . . . ? O C1 C9 C8 -87.6(2) . . . . ? N C1 C9 C8 31.7(2) . . . . ? C2 C1 C9 C8 145.16(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O H1A N 0.84 1.99 2.803(2) 163.2 3_766 _diffrn_measured_fraction_theta_max 0.886 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.465 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.078 #===END data_compound_10 _database_code_CSD 170514 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H11 Br2 N O2' _chemical_formula_weight 325.01 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' '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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.9285(7) _cell_length_b 15.3908(13) _cell_length_c 8.6509(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.781(2) _cell_angle_gamma 90.00 _cell_volume 1054.39(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6037 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 28.45 _exptl_crystal_description Tablet _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.047 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 7.661 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.197 _exptl_absorpt_correction_T_max 0.356 _exptl_absorpt_process_details 'sadabs, Bruker' _exptl_special_details ; ; _diffrn_ambient_temperature 150(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 'Bruker SMART CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10838 _diffrn_reflns_av_R_equivalents 0.0490 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 28.77 _reflns_number_total 2518 _reflns_number_gt 2181 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0447P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geometrically placed, except OH from del-F' _refine_ls_hydrogen_treatment 'Riding on parent atom, except OH as rigid body' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2518 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0321 _refine_ls_R_factor_gt 0.0260 _refine_ls_wR_factor_ref 0.0675 _refine_ls_wR_factor_gt 0.0659 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 Br1 Br 0.19621(3) 0.347598(17) -0.01233(3) 0.02615(9) Uani 1 1 d . . . Br2 Br 0.24667(3) 0.227099(16) 0.27961(3) 0.02880(9) Uani 1 1 d . . . N N -0.1388(2) 0.46276(12) 0.3026(2) 0.0166(4) Uani 1 1 d . . . O1 O 0.1119(2) 0.53220(10) 0.26101(18) 0.0206(3) Uani 1 1 d . . . C1 C -0.0303(3) 0.53073(14) 0.3114(2) 0.0165(4) Uani 1 1 d . . . C2 C -0.1169(3) 0.60143(15) 0.3934(2) 0.0192(5) Uani 1 1 d . . . H2A H -0.0680 0.6557 0.4226 0.023 Uiso 1 1 calc R . . C3 C -0.2736(3) 0.57667(15) 0.4195(3) 0.0195(5) Uani 1 1 d . . . H3A H -0.3554 0.6117 0.4665 0.023 Uiso 1 1 calc R . . O4 O -0.3476(2) 0.42841(11) 0.48327(18) 0.0214(4) Uani 1 1 d . . . H4 H -0.2763 0.4322 0.5580 0.032 Uiso 1 1 calc R . . C4 C -0.3024(3) 0.48552(15) 0.3641(3) 0.0181(5) Uani 1 1 d . . . C5 C -0.4255(3) 0.46834(16) 0.2259(3) 0.0220(5) Uani 1 1 d . . . H5A H -0.5411 0.4571 0.2596 0.026 Uiso 1 1 calc R . . H5B H -0.4284 0.5176 0.1522 0.026 Uiso 1 1 calc R . . C6 C -0.3493(3) 0.38752(17) 0.1555(3) 0.0252(5) Uani 1 1 d . . . H6A H -0.3876 0.3814 0.0454 0.030 Uiso 1 1 calc R . . H6B H -0.3823 0.3347 0.2121 0.030 Uiso 1 1 calc R . . C7 C -0.1567(3) 0.40121(15) 0.1711(3) 0.0188(5) Uani 1 1 d . . . H7A H -0.1167 0.4292 0.0752 0.023 Uiso 1 1 calc R . . C8 C -0.0602(3) 0.31719(15) 0.2029(3) 0.0202(5) Uani 1 1 d . . . H8A H -0.0876 0.2951 0.3062 0.024 Uiso 1 1 calc R . . H8B H -0.0982 0.2732 0.1253 0.024 Uiso 1 1 calc R . . C9 C 0.1289(3) 0.32807(14) 0.1978(2) 0.0184(5) Uani 1 1 d . . . H9A H 0.1636 0.3796 0.2623 0.022 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 0.02372(15) 0.03314(16) 0.02212(14) 0.00639(9) 0.00635(9) 0.00460(10) Br2 0.03345(16) 0.02558(15) 0.02742(15) 0.00601(10) 0.00189(10) 0.01211(11) N 0.0121(9) 0.0167(9) 0.0211(9) -0.0022(7) 0.0014(7) 0.0009(7) O1 0.0155(8) 0.0215(9) 0.0252(8) -0.0009(6) 0.0038(6) -0.0025(6) C1 0.0157(11) 0.0162(11) 0.0173(10) 0.0026(8) -0.0010(8) 0.0008(8) C2 0.0215(12) 0.0156(11) 0.0203(11) 0.0002(9) 0.0002(9) 0.0003(9) C3 0.0204(12) 0.0178(12) 0.0202(11) 0.0002(8) 0.0017(9) 0.0023(9) O4 0.0181(8) 0.0224(9) 0.0236(8) 0.0033(7) 0.0011(6) -0.0046(7) C4 0.0133(11) 0.0197(12) 0.0214(11) -0.0001(9) 0.0022(8) -0.0011(9) C5 0.0147(11) 0.0283(13) 0.0230(11) 0.0004(9) -0.0005(9) -0.0008(10) C6 0.0181(12) 0.0295(13) 0.0278(12) -0.0090(10) -0.0006(9) -0.0024(10) C7 0.0185(11) 0.0187(12) 0.0192(11) -0.0041(9) 0.0007(8) -0.0011(9) C8 0.0200(12) 0.0166(12) 0.0241(12) -0.0023(9) 0.0031(9) -0.0002(9) C9 0.0220(12) 0.0158(11) 0.0175(10) -0.0006(8) 0.0018(9) 0.0031(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 C9 1.943(2) . ? Br2 C9 1.930(2) . ? N C1 1.354(3) . ? N C4 1.468(3) . ? N C7 1.482(3) . ? O1 C1 1.228(3) . ? C1 C2 1.485(3) . ? C2 C3 1.330(3) . ? C3 C4 1.497(3) . ? O4 C4 1.414(3) . ? C4 C5 1.529(3) . ? C5 C6 1.523(3) . ? C6 C7 1.541(3) . ? C7 C8 1.520(3) . ? C8 C9 1.512(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 C1 N C4 111.43(18) . . ? C1 N C7 125.03(19) . . ? C4 N C7 112.16(17) . . ? O1 C1 N 125.8(2) . . ? O1 C1 C2 127.6(2) . . ? N C1 C2 106.60(19) . . ? C3 C2 C1 109.2(2) . . ? C2 C3 C4 110.1(2) . . ? O4 C4 N 112.05(18) . . ? O4 C4 C3 112.91(18) . . ? N C4 C3 102.47(17) . . ? O4 C4 C5 106.73(18) . . ? N C4 C5 102.54(17) . . ? C3 C4 C5 119.6(2) . . ? C6 C5 C4 101.74(19) . . ? C5 C6 C7 105.30(19) . . ? N C7 C8 112.11(18) . . ? N C7 C6 102.26(17) . . ? C8 C7 C6 112.8(2) . . ? C9 C8 C7 113.04(19) . . ? C8 C9 Br2 111.30(16) . . ? C8 C9 Br1 111.25(16) . . ? Br2 C9 Br1 108.52(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N C1 O1 -175.7(2) . . . . ? C7 N C1 O1 -35.4(3) . . . . ? C4 N C1 C2 4.5(2) . . . . ? C7 N C1 C2 144.9(2) . . . . ? O1 C1 C2 C3 175.6(2) . . . . ? N C1 C2 C3 -4.6(2) . . . . ? C1 C2 C3 C4 2.8(2) . . . . ? C1 N C4 O4 -124.2(2) . . . . ? C7 N C4 O4 90.2(2) . . . . ? C1 N C4 C3 -2.9(2) . . . . ? C7 N C4 C3 -148.53(18) . . . . ? C1 N C4 C5 121.71(19) . . . . ? C7 N C4 C5 -23.9(2) . . . . ? C2 C3 C4 O4 120.6(2) . . . . ? C2 C3 C4 N -0.1(2) . . . . ? C2 C3 C4 C5 -112.6(2) . . . . ? O4 C4 C5 C6 -80.5(2) . . . . ? N C4 C5 C6 37.5(2) . . . . ? C3 C4 C5 C6 149.9(2) . . . . ? C4 C5 C6 C7 -38.6(2) . . . . ? C1 N C7 C8 99.0(2) . . . . ? C4 N C7 C8 -120.9(2) . . . . ? C1 N C7 C6 -140.0(2) . . . . ? C4 N C7 C6 0.1(2) . . . . ? C5 C6 C7 N 24.1(2) . . . . ? C5 C6 C7 C8 144.7(2) . . . . ? N C7 C8 C9 -72.7(2) . . . . ? C6 C7 C8 C9 172.56(18) . . . . ? C7 C8 C9 Br2 168.18(15) . . . . ? C7 C8 C9 Br1 -70.7(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4 O1 0.84 2.06 2.890(2) 168.4 3_566 _diffrn_measured_fraction_theta_max 0.915 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.656 _refine_diff_density_min -0.559 _refine_diff_density_rms 0.099 #===END data_compound_11 _database_code_CSD 170515 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H8 Br N O' _chemical_formula_sum 'C9 H8 Br N O' _chemical_formula_weight 226.07 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.471(3) _cell_length_b 7.526(4) _cell_length_c 9.411(4) _cell_angle_alpha 70.19(3) _cell_angle_beta 68.20(3) _cell_angle_gamma 62.54(3) _cell_volume 426.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 16 _cell_measurement_theta_min 15 _cell_measurement_theta_max 16 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.759 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 4.761 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.270 _exptl_absorpt_correction_T_max 0.721 _exptl_absorpt_process_details 'X-RED (Stoe & Cie, 1997b)' _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 'Stoe Stadi-4 four-circle' _diffrn_measurement_method omega/theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 'random variation +-5.1' _diffrn_reflns_number 2857 _diffrn_reflns_av_R_equivalents 0.047 _diffrn_reflns_av_sigmaI/netI 0.048 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1658 _reflns_number_gt 1360 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STADI4 (Stoe & Cie, 1997a)' _computing_cell_refinement STADI4 _computing_data_reduction 'X-RED (Stoe & Cie, 1997b)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1994)' _computing_publication_material 'SHELXL-97; PLATON (Spek, 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^)+(0.027P)^2^+0.515P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens 'geometrically placed' _refine_ls_hydrogen_treatment 'riding model' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef ? _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1658 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0578 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.0986 _refine_ls_wR_factor_gt 0.0891 _refine_ls_goodness_of_fit_ref 1.18 _refine_ls_restrained_S_all 1.18 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N N 0.8043(5) 0.0828(5) 0.1806(4) 0.0379(8) Uani 1 1 d . . . C1 C 0.5488(7) 0.3949(7) 0.2514(6) 0.0434(10) Uani 1 1 d . . . O1 O 0.4116(5) 0.5655(5) 0.2443(5) 0.0584(9) Uani 1 1 d . . . C2 C 0.6725(7) 0.2801(7) 0.3631(6) 0.0504(12) Uani 1 1 d . . . H2 H 0.6643 0.3244 0.4472 0.060 Uiso 1 1 calc R . . C3 C 0.8029(7) 0.0962(7) 0.3240(5) 0.0428(10) Uani 1 1 d . . . C4 C 0.9207(8) -0.1107(8) 0.4034(6) 0.0580(13) Uani 1 1 d . . . H4A H 0.8760 -0.1246 0.5161 0.070 Uiso 1 1 calc R . . H4B H 1.0698 -0.1431 0.3681 0.070 Uiso 1 1 calc R . . C5 C 0.8620(9) -0.2452(8) 0.3519(6) 0.0603(13) Uani 1 1 d . . . H5A H 0.7467 -0.2764 0.4307 0.072 Uiso 1 1 calc R . . H5B H 0.9799 -0.3724 0.3347 0.072 Uiso 1 1 calc R . . C6 C 0.7981(7) -0.1181(7) 0.1979(6) 0.0458(11) Uani 1 1 d . . . H6 H 0.8968 -0.1827 0.1094 0.055 Uiso 1 1 calc R . . C7 C 0.5770(7) -0.0555(7) 0.1960(5) 0.0465(11) Uani 1 1 d . . . H7 H 0.5142 -0.1462 0.2158 0.056 Uiso 1 1 calc R . . C8 C 0.4840(7) 0.1446(7) 0.1627(5) 0.0400(10) Uani 1 1 d . . . Br Br 0.20954(8) 0.29222(8) 0.13938(6) 0.0543(2) Uani 1 1 d . . . C9 C 0.6207(6) 0.2546(6) 0.1372(5) 0.0385(9) Uani 1 1 d . . . H9 H 0.6547 0.3246 0.0280 0.046 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 N 0.0317(18) 0.045(2) 0.0342(18) -0.0098(15) -0.0022(15) -0.0163(16) C1 0.038(2) 0.040(3) 0.055(3) -0.011(2) -0.006(2) -0.021(2) O1 0.054(2) 0.0421(19) 0.077(2) -0.0165(17) -0.0172(18) -0.0129(17) C2 0.044(3) 0.057(3) 0.060(3) -0.024(2) -0.019(2) -0.015(2) C3 0.035(2) 0.053(3) 0.043(2) -0.014(2) -0.0100(19) -0.016(2) C4 0.054(3) 0.061(3) 0.049(3) -0.013(2) -0.022(2) -0.006(3) C5 0.056(3) 0.046(3) 0.061(3) -0.004(2) -0.016(3) -0.010(2) C6 0.044(3) 0.039(2) 0.050(3) -0.016(2) -0.007(2) -0.011(2) C7 0.055(3) 0.045(3) 0.051(3) -0.014(2) -0.013(2) -0.025(2) C8 0.039(2) 0.049(3) 0.037(2) -0.009(2) -0.0107(19) -0.020(2) Br 0.0415(3) 0.0684(4) 0.0584(4) -0.0161(2) -0.0152(2) -0.0216(2) C9 0.035(2) 0.042(2) 0.037(2) -0.0053(18) -0.0046(18) -0.0189(19) _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 N C3 1.383(5) . Yes N C6 1.486(5) . Yes N C9 1.464(6) . Yes C1 O1 1.218(5) . Yes C1 C2 1.440(7) . ? C1 C9 1.542(6) . ? C2 C3 1.355(6) . ? C3 C4 1.481(7) . ? C4 C5 1.533(7) . ? C5 C6 1.548(7) . ? C6 C7 1.500(7) . ? C7 C8 1.314(6) . Yes C8 C9 1.499(6) . ? C8 Br 1.886(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N C6 108.1(4) . . Yes C3 N C9 106.8(3) . . Yes C6 N C9 112.3(3) . . Yes O1 C1 C2 129.6(4) . . ? O1 C1 C9 124.6(4) . . ? C2 C1 C9 105.9(4) . . ? C3 C2 C1 107.9(4) . . ? C2 C3 N 113.6(4) . . ? C2 C3 C4 137.1(4) . . Yes N C3 C4 108.3(4) . . ? C3 C4 C5 101.5(4) . . ? C4 C5 C6 105.5(4) . . ? N C6 C7 101.3(3) . . ? N C6 C5 104.0(4) . . ? C7 C6 C5 117.9(4) . . ? C6 C7 C8 110.9(4) . . Yes C7 C8 C9 113.6(4) . . ? C7 C8 Br 125.9(3) . . ? C9 C8 Br 120.5(3) . . ? N C9 C8 100.5(3) . . ? N C9 C1 103.6(3) . . ? C8 C9 C1 116.5(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 179.1(5) . . . . ? C9 C1 C2 C3 0.3(5) . . . . ? C1 C2 C3 N 9.3(6) . . . . ? C1 C2 C3 C4 -157.4(6) . . . . ? C9 N C3 C2 -15.2(5) . . . . ? C6 N C3 C2 -136.2(4) . . . . ? C9 N C3 C4 155.3(4) . . . . ? C6 N C3 C4 34.3(5) . . . . ? C2 C3 C4 C5 131.2(6) . . . . ? N C3 C4 C5 -36.0(5) . . . . ? C3 C4 C5 C6 23.7(5) . . . . ? C3 N C6 C7 105.8(4) . . . . ? C9 N C6 C7 -11.8(4) . . . . ? C3 N C6 C5 -17.1(5) . . . . ? C9 N C6 C5 -134.6(4) . . . . ? C4 C5 C6 N -5.3(5) . . . . ? C4 C5 C6 C7 -116.5(5) . . . . ? N C6 C7 C8 7.2(5) . . . . ? C5 C6 C7 C8 119.9(5) . . . . ? C6 C7 C8 C9 -0.4(5) . . . . ? C6 C7 C8 Br 177.4(3) . . . . ? C3 N C9 C8 -106.9(4) . . . . ? C6 N C9 C8 11.4(4) . . . . ? C3 N C9 C1 13.9(4) . . . . ? C6 N C9 C1 132.2(4) . . . . ? C7 C8 C9 N -6.7(5) . . . . ? Br C8 C9 N 175.4(3) . . . . ? C7 C8 C9 C1 -117.8(5) . . . . ? Br C8 C9 C1 64.3(5) . . . . ? O1 C1 C9 N 172.4(4) . . . . ? C2 C1 C9 N -8.7(5) . . . . ? O1 C1 C9 C8 -78.3(6) . . . . ? C2 C1 C9 C8 100.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.58 _refine_diff_density_min -0.44 _refine_diff_density_rms 0.08 #===END data_compound_12 _database_code_CSD 170516 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H11 Br2 N O2' _chemical_formula_sum 'C9 H11 Br2 N O2' _chemical_formula_weight 325.01 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.5196(9) _cell_length_b 8.2050(10) _cell_length_c 10.465(2) _cell_angle_alpha 100.683(2) _cell_angle_beta 97.512(3) _cell_angle_gamma 112.135(3) _cell_volume 497.04(13) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1726 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 28.1 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.172 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 8.126 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.311 _exptl_absorpt_correction_T_max 0.483 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ; _diffrn_ambient_temperature 150(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 'Bruker SMART CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 3156 _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_av_sigmaI/netI 0.034 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.96 _reflns_number_total 1885 _reflns_number_gt 1574 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART version 5.054 (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT version 6.01 (Bruker, 1999)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC version 5.03 (Sheldrick, 1994)' _computing_publication_material 'SHELXL-97; PLATON (Spek, 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^)+(0.0922P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens 'O-H from circular delta-F synthesis, others placed geometrically' _refine_ls_hydrogen_treatment 'O-H as part of rigid rotating group, others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1885 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.125 _refine_ls_wR_factor_gt 0.120 _refine_ls_goodness_of_fit_ref 1.02 _refine_ls_restrained_S_all 1.02 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N N 0.3544(7) -0.0453(5) 0.1419(4) 0.0160(9) Uani 1 1 d . . . C1 C 0.5722(8) 0.1056(7) 0.2166(5) 0.0175(10) Uani 1 1 d . . . O1 O 0.7446(6) 0.1384(5) 0.1461(3) 0.0210(8) Uani 1 1 d . . . H1O H 0.6903 0.1264 0.0659 0.031 Uiso 1 1 calc R . . C2 C 0.6515(9) 0.0332(8) 0.3345(5) 0.0238(12) Uani 1 1 d . . . O2 O 0.8262(7) 0.1162(6) 0.4166(4) 0.0311(10) Uani 1 1 d . . . C3 C 0.4783(10) -0.1559(8) 0.3218(5) 0.0259(12) Uani 1 1 d . . . H3A H 0.3840 -0.1552 0.3886 0.031 Uiso 1 1 calc R . . H3B H 0.5530 -0.2386 0.3342 0.031 Uiso 1 1 calc R . . C4 C 0.3354(10) -0.2144(7) 0.1818(6) 0.0266(12) Uani 1 1 d . . . H4 H 0.3963 -0.2838 0.1201 0.032 Uiso 1 1 calc R . . C5 C 0.0818(10) -0.3209(8) 0.1624(6) 0.0293(13) Uani 1 1 d . . . H5A H 0.0478 -0.4168 0.2115 0.035 Uiso 1 1 calc R . . H5B H 0.0082 -0.3772 0.0669 0.035 Uiso 1 1 calc R . . C6 C 0.0060(9) -0.1726(7) 0.2211(5) 0.0206(11) Uani 1 1 d . . . H6A H -0.1552 -0.2058 0.1812 0.025 Uiso 1 1 calc R . . H6B H 0.0259 -0.1523 0.3190 0.025 Uiso 1 1 calc R . . C7 C 0.1622(8) -0.0032(7) 0.1846(5) 0.0191(10) Uani 1 1 d . . . H7 H 0.0762 0.0188 0.1081 0.023 Uiso 1 1 calc R . . C8 C 0.2769(8) 0.1721(7) 0.2966(5) 0.0185(10) Uani 1 1 d . . . H8A H 0.1892 0.2478 0.2960 0.022 Uiso 1 1 calc R . . H8B H 0.2953 0.1456 0.3849 0.022 Uiso 1 1 calc R . . C9 C 0.5023(8) 0.2638(7) 0.2634(5) 0.0184(10) Uani 1 1 d . . . Br1 Br 0.45711(9) 0.36554(7) 0.11168(5) 0.0251(2) Uani 1 1 d . . . Br2 Br 0.72899(9) 0.46132(7) 0.40535(5) 0.0272(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 N 0.019(2) 0.012(2) 0.021(2) 0.0087(17) 0.0110(17) 0.0070(17) C1 0.012(2) 0.022(3) 0.018(2) 0.005(2) 0.0028(19) 0.006(2) O1 0.0136(18) 0.032(2) 0.0186(17) 0.0083(16) 0.0058(14) 0.0095(16) C2 0.030(3) 0.036(3) 0.023(3) 0.014(2) 0.016(2) 0.026(3) O2 0.028(2) 0.048(3) 0.022(2) 0.0074(19) 0.0009(17) 0.022(2) C3 0.033(3) 0.030(3) 0.027(3) 0.016(2) 0.016(2) 0.020(3) C4 0.038(3) 0.017(3) 0.035(3) 0.014(2) 0.019(3) 0.016(2) C5 0.029(3) 0.020(3) 0.036(3) 0.005(2) 0.015(3) 0.006(2) C6 0.018(3) 0.015(3) 0.022(3) 0.003(2) 0.001(2) 0.003(2) C7 0.015(2) 0.021(3) 0.025(3) 0.009(2) 0.005(2) 0.008(2) C8 0.016(3) 0.020(3) 0.022(3) 0.005(2) 0.005(2) 0.009(2) C9 0.019(3) 0.019(3) 0.019(2) 0.008(2) 0.004(2) 0.008(2) Br1 0.0306(4) 0.0219(3) 0.0279(3) 0.0131(2) 0.0080(2) 0.0127(3) Br2 0.0246(3) 0.0225(3) 0.0262(3) 0.0010(2) 0.0038(2) 0.0040(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 N C1 1.478(6) . ? N C4 1.488(6) . ? N C7 1.518(6) . ? C1 O1 1.393(6) . ? C1 C9 1.550(7) . ? C1 C2 1.575(7) . ? C2 O2 1.201(7) . ? C2 C3 1.504(8) . ? C3 C4 1.513(8) . ? C4 C5 1.515(8) . ? C5 C6 1.536(7) . ? C6 C7 1.532(7) . ? C7 C8 1.529(7) . ? C8 C9 1.498(7) . ? C9 Br1 1.965(5) . ? C9 Br2 1.935(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 C1 N C4 109.3(4) . . ? C1 N C7 108.5(4) . . ? C4 N C7 105.7(4) . . ? O1 C1 N 114.0(4) . . ? O1 C1 C9 117.3(4) . . ? N C1 C9 103.0(4) . . ? O1 C1 C2 104.9(4) . . ? N C1 C2 103.9(4) . . ? C9 C1 C2 113.1(4) . . ? O2 C2 C3 127.2(5) . . ? O2 C2 C1 124.2(5) . . ? C3 C2 C1 108.6(4) . . ? C2 C3 C4 104.7(4) . . ? N C4 C3 106.8(4) . . ? N C4 C5 103.6(4) . . ? C3 C4 C5 117.4(5) . . ? C4 C5 C6 102.2(4) . . ? C7 C6 C5 103.9(4) . . ? N C7 C8 105.5(4) . . ? N C7 C6 106.4(4) . . ? C8 C7 C6 116.6(4) . . ? C9 C8 C7 102.7(4) . . ? C8 C9 C1 103.8(4) . . ? C8 C9 Br2 115.3(3) . . ? C1 C9 Br2 113.6(3) . . ? C8 C9 Br1 108.5(3) . . ? C1 C9 Br1 108.3(3) . . ? Br2 C9 Br1 107.0(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N C1 O1 97.3(5) . . . . ? C7 N C1 O1 -147.9(4) . . . . ? C4 N C1 C9 -134.6(4) . . . . ? C7 N C1 C9 -19.7(5) . . . . ? C4 N C1 C2 -16.3(5) . . . . ? C7 N C1 C2 98.5(4) . . . . ? O1 C1 C2 O2 58.4(6) . . . . ? N C1 C2 O2 178.3(4) . . . . ? C9 C1 C2 O2 -70.7(6) . . . . ? O1 C1 C2 C3 -119.3(4) . . . . ? N C1 C2 C3 0.6(5) . . . . ? C9 C1 C2 C3 111.6(5) . . . . ? O2 C2 C3 C4 -162.9(5) . . . . ? C1 C2 C3 C4 14.7(5) . . . . ? C1 N C4 C3 26.3(5) . . . . ? C7 N C4 C3 -90.2(5) . . . . ? C1 N C4 C5 150.9(4) . . . . ? C7 N C4 C5 34.3(5) . . . . ? C2 C3 C4 N -24.7(5) . . . . ? C2 C3 C4 C5 -140.3(4) . . . . ? N C4 C5 C6 -43.1(5) . . . . ? C3 C4 C5 C6 74.3(6) . . . . ? C4 C5 C6 C7 35.1(5) . . . . ? C1 N C7 C8 -4.6(5) . . . . ? C4 N C7 C8 112.5(4) . . . . ? C1 N C7 C6 -129.1(4) . . . . ? C4 N C7 C6 -12.0(5) . . . . ? C5 C6 C7 N -14.6(5) . . . . ? C5 C6 C7 C8 -131.9(5) . . . . ? N C7 C8 C9 27.9(5) . . . . ? C6 C7 C8 C9 145.7(4) . . . . ? C7 C8 C9 C1 -40.2(5) . . . . ? C7 C8 C9 Br2 -165.1(3) . . . . ? C7 C8 C9 Br1 74.9(4) . . . . ? O1 C1 C9 C8 163.6(4) . . . . ? N C1 C9 C8 37.5(5) . . . . ? C2 C1 C9 C8 -74.1(5) . . . . ? O1 C1 C9 Br2 -70.5(5) . . . . ? N C1 C9 Br2 163.5(3) . . . . ? C2 C1 C9 Br2 51.9(5) . . . . ? O1 C1 C9 Br1 48.4(5) . . . . ? N C1 C9 Br1 -77.7(4) . . . . ? C2 C1 C9 Br1 170.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.96 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.98 _refine_diff_density_min -1.01 _refine_diff_density_rms 0.18 #===END data_compound_14 _database_code_CSD 170517 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 Br3 N O' _chemical_formula_weight 387.91 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0950(14) _cell_length_b 7.9444(16) _cell_length_c 10.663(2) _cell_angle_alpha 77.401(4) _cell_angle_beta 79.163(3) _cell_angle_gamma 66.936(3) _cell_volume 536.15(18) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2238 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 28.4 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 11.251 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.060 _exptl_absorpt_correction_T_max 0.132 _exptl_absorpt_process_details ? _exptl_special_details ; ; _diffrn_ambient_temperature 150(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 'Bruker SMART CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3336 _diffrn_reflns_av_R_equivalents 0.0027 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 28.56 _reflns_number_total 2337 _reflns_number_gt 2039 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0896P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens ; geometrically placed, except OH from Fourier synthesis ; _refine_ls_hydrogen_treatment 'riding model, except OH refined as rigid body' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.017(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2337 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1151 _refine_ls_wR_factor_gt 0.1123 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 0.31178(8) -0.37679(6) 0.88127(5) 0.02280(19) Uani 1 1 d . . . Br2 Br 0.41575(7) -0.29691(6) 0.58122(5) 0.02068(18) Uani 1 1 d . . . Br3 Br -0.21839(7) -0.22766(7) 0.93647(5) 0.02196(18) Uani 1 1 d . . . N N 0.0098(6) 0.1035(5) 0.6359(4) 0.0139(8) Uani 1 1 d . . . O1 O -0.0411(5) -0.1813(4) 0.6348(3) 0.0159(6) Uani 1 1 d . . . H1 H -0.0027 -0.1574 0.5557 0.024 Uiso 1 1 calc R . . C2 C -0.1388(7) -0.0444(6) 0.8221(4) 0.0172(9) Uani 1 1 d . . . C8 C 0.3161(8) -0.0256(6) 0.7423(5) 0.0189(10) Uani 1 1 d . . . H8A H 0.4677 -0.0610 0.7265 0.023 Uiso 1 1 calc R . . H8B H 0.2661 0.0147 0.8280 0.023 Uiso 1 1 calc R . . C3 C -0.2392(8) 0.1354(7) 0.8211(5) 0.0216(10) Uani 1 1 d . . . H3A H -0.3503 0.1872 0.8836 0.026 Uiso 1 1 calc R . . C9 C 0.2529(7) -0.1819(6) 0.7325(4) 0.0160(9) Uani 1 1 d . . . C1 C 0.0187(7) -0.0855(6) 0.7040(4) 0.0140(9) Uani 1 1 d . . . C7 C 0.2095(7) 0.1241(6) 0.6352(5) 0.0171(9) Uani 1 1 d . . . H7A H 0.2948 0.1040 0.5499 0.020 Uiso 1 1 calc R . . C6 C 0.1505(8) 0.3246(6) 0.6554(5) 0.0220(10) Uani 1 1 d . . . H6A H 0.2580 0.3370 0.6959 0.026 Uiso 1 1 calc R . . H6B H 0.1307 0.4104 0.5722 0.026 Uiso 1 1 calc R . . C4 C -0.1564(7) 0.2470(6) 0.7096(5) 0.0185(10) Uani 1 1 d . . . H4A H -0.2676 0.3274 0.6538 0.022 Uiso 1 1 calc R . . C5 C -0.0518(8) 0.3638(7) 0.7453(5) 0.0241(11) Uani 1 1 d . . . H5A H -0.1389 0.4972 0.7308 0.029 Uiso 1 1 calc R . . H5B H -0.0251 0.3262 0.8371 0.029 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 0.0278(3) 0.0169(3) 0.0201(3) 0.00352(19) -0.0068(2) -0.0059(2) Br2 0.0209(3) 0.0180(3) 0.0211(3) -0.00772(19) 0.00250(19) -0.00483(19) Br3 0.0273(3) 0.0240(3) 0.0166(3) -0.00138(19) 0.00182(19) -0.0144(2) N 0.0186(18) 0.0096(17) 0.0136(19) -0.0018(14) -0.0016(15) -0.0055(14) O1 0.0228(16) 0.0159(15) 0.0113(16) -0.0020(12) -0.0027(13) -0.0094(13) C2 0.021(2) 0.018(2) 0.013(2) -0.0032(18) 0.0017(17) -0.0086(18) C8 0.026(2) 0.014(2) 0.019(2) -0.0008(17) -0.0037(19) -0.0102(18) C3 0.022(2) 0.022(2) 0.019(2) -0.0057(19) 0.0029(19) -0.0075(19) C9 0.020(2) 0.014(2) 0.013(2) -0.0027(16) -0.0006(17) -0.0060(17) C1 0.017(2) 0.012(2) 0.012(2) -0.0028(16) -0.0008(16) -0.0040(16) C7 0.023(2) 0.012(2) 0.019(2) -0.0026(17) -0.0041(18) -0.0090(17) C6 0.029(2) 0.014(2) 0.027(3) -0.0043(19) -0.006(2) -0.0095(19) C4 0.024(2) 0.011(2) 0.018(2) -0.0053(18) -0.0031(19) -0.0023(18) C5 0.032(3) 0.017(2) 0.027(3) -0.007(2) -0.004(2) -0.010(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 Br1 C9 1.939(5) . ? Br2 C9 1.971(5) . ? Br3 C2 1.881(4) . ? N C7 1.488(6) . ? N C1 1.501(5) . ? N C4 1.515(6) . ? O1 C1 1.386(5) . ? C2 C3 1.322(7) . ? C2 C1 1.519(6) . ? C8 C9 1.505(6) . ? C8 C7 1.523(6) . ? C3 C4 1.494(7) . ? C9 C1 1.591(6) . ? C7 C6 1.533(6) . ? C6 C5 1.530(7) . ? C4 C5 1.535(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 C7 N C1 110.1(3) . . ? C7 N C4 107.9(3) . . ? C1 N C4 108.5(3) . . ? C3 C2 C1 112.2(4) . . ? C3 C2 Br3 123.7(4) . . ? C1 C2 Br3 123.0(3) . . ? C9 C8 C7 101.7(4) . . ? C2 C3 C4 111.6(4) . . ? C8 C9 C1 105.1(4) . . ? C8 C9 Br1 112.2(3) . . ? C1 C9 Br1 116.6(3) . . ? C8 C9 Br2 108.8(3) . . ? C1 C9 Br2 107.8(3) . . ? Br1 C9 Br2 106.2(2) . . ? O1 C1 N 114.6(4) . . ? O1 C1 C2 107.5(4) . . ? N C1 C2 103.2(3) . . ? O1 C1 C9 114.0(3) . . ? N C1 C9 101.8(3) . . ? C2 C1 C9 115.4(4) . . ? N C7 C8 105.4(4) . . ? N C7 C6 104.9(4) . . ? C8 C7 C6 115.8(4) . . ? C5 C6 C7 104.1(4) . . ? C3 C4 N 104.2(4) . . ? C3 C4 C5 115.5(4) . . ? N C4 C5 106.6(4) . . ? C6 C5 C4 104.5(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N 0.84 2.00 2.801(5) 159.4 2_556 _diffrn_measured_fraction_theta_max 0.853 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.931 _refine_diff_density_max 1.087 _refine_diff_density_min -1.228 _refine_diff_density_rms 0.221 #===END data_compound_15 _database_code_CSD 170518 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H9 Br2 N O' _chemical_formula_weight 306.99 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' 'Br' 'Br' -0.2901 2.4595 '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 P2(1)/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 11.049(3) _cell_length_b 14.876(4) _cell_length_c 13.085(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.177(5) _cell_angle_gamma 90.00 _cell_volume 2031.4(9) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4330 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 28.13 _exptl_crystal_description column _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.008 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 7.940 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.269 _exptl_absorpt_correction_T_max 0.506 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ; _diffrn_ambient_temperature 150(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 'Bruker SMART CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14686 _diffrn_reflns_av_R_equivalents 0.070 _diffrn_reflns_av_sigmaI/netI 0.0558 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 28.83 _reflns_number_total 4806 _reflns_number_gt 3269 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0180P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geometrically placed, OH from deltaF' _refine_ls_hydrogen_treatment 'riding model, OH rigid rotating group' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4806 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0603 _refine_ls_wR_factor_gt 0.0571 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 Br1 Br 0.35764(4) 0.20396(3) 0.12537(3) 0.03383(11) Uani 1 1 d . . . O1 O 0.0429(2) 0.20956(16) 0.02762(18) 0.0237(6) Uani 1 1 d . . . H1 H -0.0326 0.1987 -0.0120 0.036 Uiso 1 1 calc R . . N1 N 0.0442(3) 0.34248(18) -0.0789(2) 0.0195(6) Uani 1 1 d . . . C1 C 0.1074(3) 0.2556(2) -0.0323(3) 0.0194(8) Uani 1 1 d . . . Br2 Br 0.15538(4) 0.08468(3) -0.12869(3) 0.04282(12) Uani 1 1 d . . . C2 C 0.2359(3) 0.2865(2) 0.0438(3) 0.0227(8) Uani 1 1 d . . . C3 C 0.2459(3) 0.3741(2) 0.0506(3) 0.0268(8) Uani 1 1 d . . . H3A H 0.3195 0.4053 0.0947 0.032 Uiso 1 1 calc R . . C4 C 0.1263(3) 0.4188(2) -0.0202(3) 0.0250(8) Uani 1 1 d . . . H4A H 0.0831 0.4512 0.0252 0.030 Uiso 1 1 calc R . . C5 C 0.1408(4) 0.4815(2) -0.1085(3) 0.0292(9) Uani 1 1 d . . . H5A H 0.0693 0.5251 -0.1319 0.035 Uiso 1 1 calc R . . H5B H 0.2229 0.5148 -0.0829 0.035 Uiso 1 1 calc R . . C6 C 0.1380(3) 0.4174(2) -0.1997(3) 0.0263(8) Uani 1 1 d . . . H6A H 0.2228 0.3891 -0.1870 0.032 Uiso 1 1 calc R . . H6B H 0.1119 0.4488 -0.2703 0.032 Uiso 1 1 calc R . . C7 C 0.0382(3) 0.3478(2) -0.1955(3) 0.0204(8) Uani 1 1 d . . . H7A H -0.0491 0.3671 -0.2423 0.025 Uiso 1 1 calc R . . C8 C 0.0644(3) 0.2549(2) -0.2221(3) 0.0231(8) Uani 1 1 d . . . H8A H 0.0526 0.2335 -0.2931 0.028 Uiso 1 1 calc R . . C9 C 0.1061(3) 0.2063(2) -0.1340(3) 0.0235(8) Uani 1 1 d . . . Br1A Br 0.32475(4) -0.42425(2) 0.27083(3) 0.03155(10) Uani 1 1 d . . . O1A O 0.1864(2) -0.33927(16) 0.03123(19) 0.0257(6) Uani 1 1 d . . . H1A H 0.1195 -0.3477 0.0471 0.039 Uiso 1 1 calc R . . N1A N 0.2193(3) -0.18736(17) 0.1000(2) 0.0195(6) Uani 1 1 d . . . C1A C 0.2677(3) -0.2817(2) 0.1065(3) 0.0191(8) Uani 1 1 d . . . Br2A Br 0.48956(4) -0.37115(3) 0.06979(3) 0.03704(11) Uani 1 1 d . . . C2A C 0.2856(3) -0.3054(2) 0.2229(3) 0.0211(8) Uani 1 1 d . . . C3A C 0.2654(3) -0.2375(2) 0.2792(3) 0.0218(8) Uani 1 1 d . . . H3AA H 0.2671 -0.2411 0.3522 0.026 Uiso 1 1 calc R . . C4A C 0.2394(3) -0.1541(2) 0.2129(3) 0.0223(8) Uani 1 1 d . . . H4AA H 0.1607 -0.1234 0.2170 0.027 Uiso 1 1 calc R . . C5A C 0.3518(3) -0.0881(2) 0.2383(3) 0.0302(9) Uani 1 1 d . . . H5AA H 0.4350 -0.1195 0.2680 0.036 Uiso 1 1 calc R . . H5AB H 0.3453 -0.0412 0.2900 0.036 Uiso 1 1 calc R . . C6A C 0.3348(4) -0.0478(2) 0.1262(3) 0.0344(10) Uani 1 1 d . . . H6AA H 0.2668 -0.0014 0.1067 0.041 Uiso 1 1 calc R . . H6AB H 0.4158 -0.0209 0.1236 0.041 Uiso 1 1 calc R . . C7A C 0.2969(3) -0.1287(2) 0.0519(3) 0.0273(9) Uani 1 1 d . . . H7AA H 0.2443 -0.1094 -0.0227 0.033 Uiso 1 1 calc R . . C8A C 0.4040(3) -0.1887(3) 0.0476(3) 0.0299(9) Uani 1 1 d . . . H8AA H 0.4741 -0.1696 0.0263 0.036 Uiso 1 1 calc R . . C9A C 0.3886(3) -0.2705(2) 0.0770(3) 0.0243(8) 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 Br1 0.0218(2) 0.0386(2) 0.0335(2) 0.00677(18) -0.00118(17) 0.00525(18) O1 0.0159(13) 0.0329(15) 0.0193(13) 0.0043(11) 0.0016(11) -0.0025(11) N1 0.0164(16) 0.0231(16) 0.0172(16) 0.0012(12) 0.0032(13) 0.0012(12) C1 0.018(2) 0.0236(19) 0.0151(19) 0.0012(14) 0.0035(16) -0.0020(15) Br2 0.0587(3) 0.0260(2) 0.0375(3) -0.00461(19) 0.0073(2) 0.0109(2) C2 0.0172(19) 0.030(2) 0.0188(19) 0.0026(16) 0.0032(16) 0.0042(16) C3 0.019(2) 0.033(2) 0.026(2) -0.0071(17) 0.0038(17) -0.0039(17) C4 0.026(2) 0.024(2) 0.024(2) -0.0056(16) 0.0064(17) 0.0013(17) C5 0.032(2) 0.020(2) 0.036(2) 0.0037(17) 0.0122(19) 0.0001(17) C6 0.024(2) 0.027(2) 0.030(2) 0.0035(17) 0.0116(18) 0.0008(16) C7 0.0168(19) 0.024(2) 0.0186(19) 0.0034(15) 0.0029(16) 0.0015(15) C8 0.025(2) 0.028(2) 0.0155(19) -0.0036(16) 0.0048(17) -0.0066(16) C9 0.025(2) 0.0203(19) 0.023(2) -0.0016(16) 0.0049(17) 0.0018(16) Br1A 0.0358(2) 0.0239(2) 0.0348(2) 0.00530(17) 0.01145(19) 0.00389(17) O1A 0.0168(14) 0.0305(15) 0.0278(15) -0.0111(11) 0.0044(12) -0.0026(11) N1A 0.0197(16) 0.0219(16) 0.0144(15) -0.0014(12) 0.0023(13) -0.0014(12) C1A 0.0154(18) 0.027(2) 0.0133(18) -0.0013(15) 0.0020(15) -0.0001(15) Br2A 0.0231(2) 0.0501(3) 0.0388(3) -0.0038(2) 0.01132(19) 0.00962(19) C2A 0.0147(19) 0.021(2) 0.026(2) 0.0030(15) 0.0047(16) -0.0018(15) C3A 0.020(2) 0.028(2) 0.0166(19) -0.0019(15) 0.0050(16) -0.0030(16) C4A 0.023(2) 0.022(2) 0.020(2) -0.0041(15) 0.0047(16) 0.0014(15) C5A 0.029(2) 0.026(2) 0.030(2) -0.0039(17) 0.0025(18) -0.0021(17) C6A 0.033(2) 0.031(2) 0.040(3) 0.0029(19) 0.012(2) -0.0069(18) C7A 0.027(2) 0.030(2) 0.024(2) 0.0050(17) 0.0061(17) -0.0047(17) C8A 0.020(2) 0.045(3) 0.024(2) -0.0028(18) 0.0073(18) -0.0068(18) C9A 0.0153(19) 0.035(2) 0.021(2) -0.0076(16) 0.0035(16) -0.0015(16) _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 C2 1.874(3) . ? O1 C1 1.400(4) . ? N1 C1 1.500(4) . ? N1 C4 1.498(4) . ? N1 C7 1.508(4) . ? C1 C2 1.514(4) . ? C1 C9 1.515(4) . ? Br2 C9 1.885(3) . ? C2 C3 1.308(5) . ? C3 C4 1.497(5) . ? C4 C5 1.534(4) . ? C5 C6 1.520(5) . ? C6 C7 1.526(4) . ? C7 C8 1.477(4) . ? C8 C9 1.309(4) . ? Br1A C2A 1.879(3) . ? O1A C1A 1.389(4) . ? N1A C1A 1.494(4) . ? N1A C4A 1.503(4) . ? N1A C7A 1.499(4) . ? C1A C2A 1.512(4) . ? C1A C9A 1.516(4) . ? Br2A C9A 1.888(4) . ? C2A C3A 1.312(4) . ? C3A C4A 1.487(4) . ? C4A C5A 1.531(5) . ? C5A C6A 1.538(5) . ? C6A C7A 1.517(5) . ? C7A C8A 1.498(5) . ? C8A C9A 1.303(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 C4 N1 C1 108.8(3) . . ? C4 N1 C7 107.2(2) . . ? C1 N1 C7 108.4(2) . . ? O1 C1 N1 113.2(3) . . ? O1 C1 C2 108.6(3) . . ? N1 C1 C2 102.5(3) . . ? O1 C1 C9 113.3(3) . . ? N1 C1 C9 101.0(3) . . ? C2 C1 C9 117.5(3) . . ? C3 C2 C1 112.7(3) . . ? C3 C2 Br1 125.8(3) . . ? C1 C2 Br1 121.2(2) . . ? C2 C3 C4 111.3(3) . . ? C3 C4 N1 104.1(3) . . ? C3 C4 C5 116.5(3) . . ? N1 C4 C5 105.7(3) . . ? C6 C5 C4 103.3(3) . . ? C5 C6 C7 103.0(3) . . ? C8 C7 N1 104.0(3) . . ? C8 C7 C6 115.2(3) . . ? N1 C7 C6 106.3(3) . . ? C9 C8 C7 110.4(3) . . ? C8 C9 C1 113.9(3) . . ? C8 C9 Br2 125.2(3) . . ? C1 C9 Br2 120.8(2) . . ? C1A N1A C7A 109.1(2) . . ? C1A N1A C4A 108.6(2) . . ? C7A N1A C4A 107.5(2) . . ? O1A C1A N1A 113.8(3) . . ? O1A C1A C2A 114.2(3) . . ? N1A C1A C2A 101.6(2) . . ? O1A C1A C9A 107.8(3) . . ? N1A C1A C9A 102.2(3) . . ? C2A C1A C9A 116.6(3) . . ? C3A C2A C1A 113.4(3) . . ? C3A C2A Br1A 126.9(3) . . ? C1A C2A Br1A 119.7(2) . . ? C2A C3A C4A 110.5(3) . . ? C3A C4A N1A 103.7(3) . . ? C3A C4A C5A 114.9(3) . . ? N1A C4A C5A 105.8(3) . . ? C4A C5A C6A 101.9(3) . . ? C7A C6A C5A 103.0(3) . . ? C8A C7A N1A 103.7(3) . . ? C8A C7A C6A 116.2(3) . . ? N1A C7A C6A 105.6(3) . . ? C9A C8A C7A 111.4(3) . . ? C8A C9A C1A 112.9(3) . . ? C8A C9A Br2A 126.1(3) . . ? C1A C9A Br2A 120.7(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 O1 109.5(3) . . . . ? C7 N1 C1 O1 -134.2(3) . . . . ? C4 N1 C1 C2 -7.3(3) . . . . ? C7 N1 C1 C2 109.0(3) . . . . ? C4 N1 C1 C9 -129.0(3) . . . . ? C7 N1 C1 C9 -12.6(3) . . . . ? O1 C1 C2 C3 -115.3(3) . . . . ? N1 C1 C2 C3 4.8(4) . . . . ? C9 C1 C2 C3 114.5(4) . . . . ? O1 C1 C2 Br1 60.2(3) . . . . ? N1 C1 C2 Br1 -179.8(2) . . . . ? C9 C1 C2 Br1 -70.1(4) . . . . ? C1 C2 C3 C4 -0.3(4) . . . . ? Br1 C2 C3 C4 -175.5(2) . . . . ? C2 C3 C4 N1 -4.4(4) . . . . ? C2 C3 C4 C5 -120.2(3) . . . . ? C1 N1 C4 C3 7.3(3) . . . . ? C7 N1 C4 C3 -109.8(3) . . . . ? C1 N1 C4 C5 130.6(3) . . . . ? C7 N1 C4 C5 13.5(3) . . . . ? C3 C4 C5 C6 82.8(4) . . . . ? N1 C4 C5 C6 -32.2(3) . . . . ? C4 C5 C6 C7 38.0(3) . . . . ? C4 N1 C7 C8 132.5(3) . . . . ? C1 N1 C7 C8 15.1(3) . . . . ? C4 N1 C7 C6 10.4(3) . . . . ? C1 N1 C7 C6 -106.9(3) . . . . ? C5 C6 C7 C8 -144.9(3) . . . . ? C5 C6 C7 N1 -30.3(3) . . . . ? N1 C7 C8 C9 -11.7(4) . . . . ? C6 C7 C8 C9 104.2(4) . . . . ? C7 C8 C9 C1 3.9(4) . . . . ? C7 C8 C9 Br2 -178.4(2) . . . . ? O1 C1 C9 C8 127.1(3) . . . . ? N1 C1 C9 C8 5.6(4) . . . . ? C2 C1 C9 C8 -104.9(4) . . . . ? O1 C1 C9 Br2 -50.7(4) . . . . ? N1 C1 C9 Br2 -172.1(2) . . . . ? C2 C1 C9 Br2 77.4(4) . . . . ? C7A N1A C1A O1A -107.2(3) . . . . ? C4A N1A C1A O1A 136.0(3) . . . . ? C7A N1A C1A C2A 129.5(3) . . . . ? C4A N1A C1A C2A 12.7(3) . . . . ? C7A N1A C1A C9A 8.8(3) . . . . ? C4A N1A C1A C9A -108.1(3) . . . . ? O1A C1A C2A C3A -128.5(3) . . . . ? N1A C1A C2A C3A -5.5(4) . . . . ? C9A C1A C2A C3A 104.6(4) . . . . ? O1A C1A C2A Br1A 48.7(4) . . . . ? N1A C1A C2A Br1A 171.6(2) . . . . ? C9A C1A C2A Br1A -78.2(3) . . . . ? C1A C2A C3A C4A -4.1(4) . . . . ? Br1A C2A C3A C4A 179.0(2) . . . . ? C2A C3A C4A N1A 11.9(4) . . . . ? C2A C3A C4A C5A -103.2(3) . . . . ? C1A N1A C4A C3A -15.2(3) . . . . ? C7A N1A C4A C3A -133.0(3) . . . . ? C1A N1A C4A C5A 106.1(3) . . . . ? C7A N1A C4A C5A -11.7(3) . . . . ? C3A C4A C5A C6A 145.9(3) . . . . ? N1A C4A C5A C6A 32.1(3) . . . . ? C4A C5A C6A C7A -40.2(3) . . . . ? C1A N1A C7A C8A -8.8(3) . . . . ? C4A N1A C7A C8A 108.7(3) . . . . ? C1A N1A C7A C6A -131.4(3) . . . . ? C4A N1A C7A C6A -13.9(4) . . . . ? C5A C6A C7A C8A -80.4(4) . . . . ? C5A C6A C7A N1A 33.8(4) . . . . ? N1A C7A C8A C9A 5.3(4) . . . . ? C6A C7A C8A C9A 120.6(3) . . . . ? C7A C8A C9A C1A 0.2(4) . . . . ? C7A C8A C9A Br2A 173.0(2) . . . . ? O1A C1A C9A C8A 114.5(3) . . . . ? N1A C1A C9A C8A -5.6(4) . . . . ? C2A C1A C9A C8A -115.5(4) . . . . ? O1A C1A C9A Br2A -58.7(3) . . . . ? N1A C1A C9A Br2A -178.9(2) . . . . ? C2A C1A C9A Br2A 71.3(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N1A 0.84 2.01 2.848(3) 172.8 3 O1A H1A N1 0.84 1.99 2.815(4) 169.0 3 _diffrn_measured_fraction_theta_max 0.905 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.550 _refine_diff_density_min -0.563 _refine_diff_density_rms 0.108 #===END