data_e _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 Br2 N4 O' _chemical_formula_weight 374.05 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)/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 14.851(3) _cell_length_b 6.8378(12) _cell_length_c 13.732(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.703(3) _cell_angle_gamma 90.00 _cell_volume 1312.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3863 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 31.15 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.892 _exptl_crystal_density_method 'none' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 6.168 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.5248 _exptl_absorpt_correction_T_max 0.5775 _exptl_absorpt_process_details ? _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9109 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_av_sigmaI/netI 0.0570 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2575 _reflns_number_gt 2058 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _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^)+(0.1163P)^2^+0.7390P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2575 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1694 _refine_ls_wR_factor_gt 0.1531 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 0.26389(4) 0.27296(9) 0.25636(4) 0.0379(2) Uani 1 1 d . . . Br2 Br 0.19705(5) 0.65893(9) 0.40870(6) 0.0575(3) Uani 1 1 d . . . C1 C 0.1241(4) 0.2758(8) 0.4209(4) 0.0325(12) Uani 1 1 d . . . C2 C 0.0992(4) 0.4694(9) 0.3955(4) 0.0398(13) Uani 1 1 d . . . C3 C 0.0064(5) 0.5314(11) 0.3630(5) 0.0497(16) Uani 1 1 d . . . H3 H -0.0080 0.6617 0.3452 0.060 Uiso 1 1 calc R . . C4 C -0.0666(4) 0.3990(12) 0.3565(5) 0.0542(17) Uani 1 1 d . . . H4 H -0.1299 0.4409 0.3341 0.065 Uiso 1 1 calc R . . C5 C -0.0456(5) 0.2083(11) 0.3829(6) 0.0551(17) Uani 1 1 d . . . H5 H -0.0941 0.1207 0.3808 0.066 Uiso 1 1 calc R . . C6 C 0.0498(4) 0.1449(10) 0.4134(5) 0.0410(13) Uani 1 1 d . . . H6 H 0.0638 0.0135 0.4288 0.049 Uiso 1 1 calc R . . C7 C 0.2218(3) 0.2010(7) 0.4491(4) 0.0258(10) Uani 1 1 d . . . C8 C 0.2825(4) 0.1830(7) 0.3891(4) 0.0275(10) Uani 1 1 d . . . C9 C 0.4268(4) -0.0316(8) 0.6193(4) 0.0328(11) Uani 1 1 d . . . H9A H 0.4869 -0.0169 0.6068 0.039 Uiso 1 1 calc R . . H9B H 0.4320 0.0391 0.6822 0.039 Uiso 1 1 calc R . . C10 C 0.4537(4) -0.3762(10) 0.5964(5) 0.0439(14) Uani 1 1 d . . . H10 H 0.4901 -0.3359 0.5567 0.053 Uiso 1 1 calc R . . C11 C 0.3513(6) -0.2882(11) 0.6955(6) 0.061(2) Uani 1 1 d . . . H11A H 0.3422 -0.4273 0.6934 0.092 Uiso 1 1 calc R . . H11B H 0.2904 -0.2245 0.6675 0.092 Uiso 1 1 calc R . . H11C H 0.3819 -0.2472 0.7658 0.092 Uiso 1 1 calc R . . N1 N 0.2669(3) 0.1163(6) 0.5407(3) 0.0280(9) Uani 1 1 d . . . N2 N 0.3504(3) 0.0545(6) 0.5334(3) 0.0295(9) Uani 1 1 d . . . N3 N 0.3620(3) 0.0922(6) 0.4439(3) 0.0282(9) Uani 1 1 d . . . N4 N 0.4113(3) -0.2359(7) 0.6342(4) 0.0374(11) Uani 1 1 d . . . O1 O 0.4486(4) -0.5510(7) 0.6095(4) 0.0670(14) 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 0.0465(4) 0.0396(4) 0.0310(3) 0.0047(2) 0.0177(3) 0.0010(2) Br2 0.0513(4) 0.0295(4) 0.0811(6) -0.0065(3) 0.0083(4) -0.0018(3) C1 0.034(3) 0.034(3) 0.031(3) 0.001(2) 0.014(2) 0.003(2) C2 0.047(3) 0.032(3) 0.037(3) -0.006(2) 0.009(2) 0.003(3) C3 0.047(3) 0.048(4) 0.052(4) 0.000(3) 0.015(3) 0.021(3) C4 0.028(3) 0.073(5) 0.058(4) 0.002(4) 0.010(3) 0.016(3) C5 0.039(3) 0.060(4) 0.070(5) 0.010(4) 0.022(3) 0.004(3) C6 0.035(3) 0.045(3) 0.048(3) 0.006(3) 0.021(3) 0.002(3) C7 0.029(2) 0.024(2) 0.028(2) 0.001(2) 0.014(2) 0.000(2) C8 0.027(2) 0.026(3) 0.032(2) -0.002(2) 0.013(2) -0.001(2) C9 0.030(3) 0.032(3) 0.036(3) 0.004(2) 0.010(2) 0.002(2) C10 0.039(3) 0.041(4) 0.053(3) -0.004(3) 0.017(3) 0.001(3) C11 0.068(5) 0.053(4) 0.078(5) 0.030(4) 0.043(4) 0.015(4) N1 0.026(2) 0.031(2) 0.028(2) 0.0025(18) 0.0100(17) 0.0035(18) N2 0.027(2) 0.029(2) 0.034(2) 0.0022(18) 0.0117(17) 0.0014(18) N3 0.026(2) 0.031(2) 0.029(2) -0.0002(18) 0.0107(17) -0.0008(18) N4 0.034(2) 0.032(3) 0.048(3) 0.008(2) 0.016(2) 0.001(2) O1 0.073(3) 0.034(3) 0.098(4) -0.003(3) 0.034(3) 0.004(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 C8 1.854(5) . ? Br2 C2 1.909(6) . ? C1 C2 1.386(8) . ? C1 C6 1.397(8) . ? C1 C7 1.462(7) . ? C2 C3 1.365(8) . ? C3 C4 1.392(10) . ? C3 H3 0.9300 . ? C4 C5 1.361(11) . ? C4 H4 0.9300 . ? C5 C6 1.404(8) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.341(6) . ? C7 C8 1.417(6) . ? C8 N3 1.322(7) . ? C9 N4 1.441(7) . ? C9 N2 1.458(7) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 O1 1.214(8) . ? C10 N4 1.344(8) . ? C10 H10 0.9300 . ? C11 N4 1.461(8) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? N1 N2 1.346(6) . ? N2 N3 1.322(6) . ? 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 117.2(5) . . ? C2 C1 C7 123.8(5) . . ? C6 C1 C7 118.9(5) . . ? C3 C2 C1 122.2(6) . . ? C3 C2 Br2 118.2(5) . . ? C1 C2 Br2 119.6(4) . . ? C2 C3 C4 119.8(6) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 120.2(6) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 119.5(7) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C1 C6 C5 121.1(6) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? N1 C7 C8 107.1(4) . . ? N1 C7 C1 122.5(4) . . ? C8 C7 C1 130.2(5) . . ? N3 C8 C7 109.3(4) . . ? N3 C8 Br1 121.6(4) . . ? C7 C8 Br1 129.1(4) . . ? N4 C9 N2 112.9(5) . . ? N4 C9 H9A 109.0 . . ? N2 C9 H9A 109.0 . . ? N4 C9 H9B 109.0 . . ? N2 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? O1 C10 N4 125.8(6) . . ? O1 C10 H10 117.1 . . ? N4 C10 H10 117.1 . . ? N4 C11 H11A 109.5 . . ? N4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C7 N1 N2 104.3(4) . . ? N3 N2 N1 114.8(4) . . ? N3 N2 C9 121.5(4) . . ? N1 N2 C9 123.5(4) . . ? C8 N3 N2 104.5(4) . . ? C10 N4 C9 121.3(5) . . ? C10 N4 C11 120.2(6) . . ? C9 N4 C11 118.4(5) . . ? 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 C6 C1 C2 C3 -0.9(8) . . . . ? C7 C1 C2 C3 175.6(5) . . . . ? C6 C1 C2 Br2 177.7(4) . . . . ? C7 C1 C2 Br2 -5.8(7) . . . . ? C1 C2 C3 C4 1.3(9) . . . . ? Br2 C2 C3 C4 -177.3(5) . . . . ? C2 C3 C4 C5 0.3(10) . . . . ? C3 C4 C5 C6 -2.1(11) . . . . ? C2 C1 C6 C5 -1.0(9) . . . . ? C7 C1 C6 C5 -177.7(6) . . . . ? C4 C5 C6 C1 2.5(10) . . . . ? C2 C1 C7 N1 120.5(6) . . . . ? C6 C1 C7 N1 -63.0(7) . . . . ? C2 C1 C7 C8 -66.3(8) . . . . ? C6 C1 C7 C8 110.2(7) . . . . ? N1 C7 C8 N3 -0.8(6) . . . . ? C1 C7 C8 N3 -174.7(5) . . . . ? N1 C7 C8 Br1 -178.7(4) . . . . ? C1 C7 C8 Br1 7.3(9) . . . . ? C8 C7 N1 N2 0.6(5) . . . . ? C1 C7 N1 N2 175.2(5) . . . . ? C7 N1 N2 N3 -0.4(6) . . . . ? C7 N1 N2 C9 174.3(5) . . . . ? N4 C9 N2 N3 -104.4(5) . . . . ? N4 C9 N2 N1 81.3(6) . . . . ? C7 C8 N3 N2 0.5(6) . . . . ? Br1 C8 N3 N2 178.7(4) . . . . ? N1 N2 N3 C8 -0.1(6) . . . . ? C9 N2 N3 C8 -174.9(5) . . . . ? O1 C10 N4 C9 176.1(6) . . . . ? O1 C10 N4 C11 -1.3(10) . . . . ? N2 C9 N4 C10 98.1(6) . . . . ? N2 C9 N4 C11 -84.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.712 _refine_diff_density_min -0.756 _refine_diff_density_rms 0.165