# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Cehpuri Ramana' _publ_contact_author_email VR.CHEPURI@NCL.RES.IN _publ_section_title ; "Click" Synthesis of Isomeric Compounds for Assessing the Efficiency of Bifurcated Br***NO2 Synthon ; loop_ _publ_author_name 'Cehpuri Ramana' 'Soumitra Chatterjee' 'Kulbhushan A. Durugkar' 'Rajesh G. Gonnade' # Attachment 'CIFS_B809985E.cif' data_8 _database_code_depnum_ccdc_archive 'CCDC 679556' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 N4 O2' _chemical_formula_sum 'C14 H10 N4 O2' _chemical_formula_weight 266.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 12.180(4) _cell_length_b 7.501(3) _cell_length_c 14.277(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.286(7) _cell_angle_gamma 90.00 _cell_volume 1283.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1175 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 24.79 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9596 _exptl_absorpt_correction_T_max 0.9753 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9605 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0432 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2513 _reflns_number_gt 1661 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0581P)^2^+0.0999P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2513 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0997 _refine_ls_R_factor_gt 0.0619 _refine_ls_wR_factor_ref 0.1475 _refine_ls_wR_factor_gt 0.1304 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.69082(19) 0.1782(3) 0.32451(17) 0.0801(7) Uani 1 1 d . . . O2 O 0.5724(2) 0.1838(3) 0.41958(16) 0.0791(7) Uani 1 1 d . . . N1 N 0.58043(17) 0.0134(3) 0.15993(14) 0.0460(5) Uani 1 1 d . . . N2 N 0.5140(2) 0.1600(3) 0.15057(17) 0.0620(7) Uani 1 1 d . . . N3 N 0.5440(2) 0.2568(3) 0.08300(17) 0.0618(7) Uani 1 1 d . . . N4 N 0.6154(2) 0.1130(3) 0.35831(16) 0.0539(6) Uani 1 1 d . . . C1 C 0.6509(2) 0.0187(4) 0.09837(18) 0.0473(7) Uani 1 1 d . . . C2 C 0.6286(2) 0.1748(3) 0.04925(18) 0.0465(6) Uani 1 1 d . . . C3 C 0.6822(2) 0.2531(3) -0.02445(17) 0.0459(6) Uani 1 1 d . . . C4 C 0.6785(3) 0.4383(4) -0.0400(2) 0.0552(8) Uani 1 1 d . . . C5 C 0.7313(3) 0.5140(5) -0.1078(2) 0.0645(8) Uani 1 1 d . . . C6 C 0.7896(3) 0.4089(5) -0.1604(2) 0.0697(9) Uani 1 1 d . . . C7 C 0.7943(3) 0.2263(5) -0.1464(2) 0.0662(9) Uani 1 1 d . . . C8 C 0.7402(3) 0.1501(4) -0.0793(2) 0.0575(7) Uani 1 1 d . . . C9 C 0.5700(2) -0.1157(3) 0.23118(18) 0.0433(6) Uani 1 1 d . . . C10 C 0.5469(2) -0.2919(3) 0.2055(2) 0.0516(7) Uani 1 1 d . . . C11 C 0.5307(3) -0.4134(4) 0.2742(2) 0.0598(8) Uani 1 1 d . . . C12 C 0.5345(3) -0.3625(4) 0.3666(2) 0.0638(8) Uani 1 1 d . . . C13 C 0.5575(2) -0.1863(4) 0.3937(2) 0.0552(7) Uani 1 1 d . . . C14 C 0.5776(2) -0.0674(3) 0.32556(18) 0.0435(6) Uani 1 1 d . . . H1 H 0.705(2) -0.068(4) 0.0924(18) 0.064(8) Uiso 1 1 d . . . H4 H 0.640(2) 0.504(4) -0.0042(19) 0.059(9) Uiso 1 1 d . . . H5 H 0.729(3) 0.648(4) -0.118(2) 0.084(10) Uiso 1 1 d . . . H6 H 0.826(2) 0.462(4) -0.204(2) 0.069(9) Uiso 1 1 d . . . H7 H 0.831(3) 0.148(5) -0.182(2) 0.095(12) Uiso 1 1 d . . . H8 H 0.742(2) 0.020(4) -0.0709(18) 0.060(8) Uiso 1 1 d . . . H10 H 0.5418(19) -0.323(3) 0.1398(18) 0.042(7) Uiso 1 1 d . . . H11 H 0.516(2) -0.535(4) 0.2523(19) 0.073(9) Uiso 1 1 d . . . H12 H 0.521(2) -0.440(4) 0.414(2) 0.071(9) Uiso 1 1 d . . . H13 H 0.562(2) -0.148(4) 0.459(2) 0.068(9) Uiso 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 O1 0.0829(16) 0.0606(14) 0.0989(17) -0.0118(12) 0.0216(14) -0.0320(12) O2 0.1145(19) 0.0518(13) 0.0734(15) -0.0139(11) 0.0233(14) 0.0035(12) N1 0.0514(13) 0.0359(12) 0.0508(13) 0.0055(10) 0.0092(10) 0.0075(10) N2 0.0686(16) 0.0499(14) 0.0718(16) 0.0165(12) 0.0248(13) 0.0225(12) N3 0.0711(16) 0.0519(14) 0.0665(16) 0.0163(13) 0.0235(13) 0.0206(12) N4 0.0623(15) 0.0411(13) 0.0551(14) -0.0022(11) 0.0022(12) -0.0028(12) C1 0.0530(16) 0.0404(15) 0.0496(16) 0.0035(12) 0.0120(13) 0.0116(13) C2 0.0516(16) 0.0425(15) 0.0446(15) 0.0012(12) 0.0062(12) 0.0091(12) C3 0.0487(15) 0.0436(15) 0.0425(15) 0.0003(12) 0.0001(12) 0.0053(12) C4 0.0627(19) 0.0493(18) 0.0525(17) 0.0050(14) 0.0070(15) 0.0064(14) C5 0.070(2) 0.058(2) 0.064(2) 0.0140(16) 0.0068(16) -0.0026(17) C6 0.068(2) 0.087(3) 0.0540(19) 0.0150(18) 0.0095(16) -0.0083(19) C7 0.0614(19) 0.084(3) 0.0532(19) -0.0052(18) 0.0112(16) 0.0060(18) C8 0.0651(19) 0.0536(18) 0.0523(17) -0.0042(15) 0.0066(14) 0.0033(15) C9 0.0416(14) 0.0383(14) 0.0488(15) 0.0047(12) 0.0044(11) 0.0028(11) C10 0.0591(18) 0.0419(16) 0.0515(17) -0.0063(13) 0.0040(14) -0.0023(12) C11 0.0658(19) 0.0398(16) 0.072(2) -0.0019(15) 0.0064(16) -0.0061(14) C12 0.075(2) 0.0452(17) 0.072(2) 0.0147(16) 0.0148(17) -0.0081(15) C13 0.0624(18) 0.0507(17) 0.0513(18) 0.0024(14) 0.0073(15) -0.0014(14) C14 0.0468(14) 0.0341(13) 0.0474(15) 0.0015(11) 0.0024(11) -0.0029(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N4 1.214(3) . ? O2 N4 1.219(3) . ? N1 C1 1.334(3) . ? N1 N2 1.358(3) . ? N1 C9 1.426(3) . ? N2 N3 1.310(3) . ? N3 C2 1.361(3) . ? N4 C14 1.478(3) . ? C1 C2 1.367(4) . ? C2 C3 1.458(3) . ? C3 C8 1.381(4) . ? C3 C4 1.406(4) . ? C4 C5 1.377(4) . ? C5 C6 1.371(4) . ? C6 C7 1.384(5) . ? C7 C8 1.379(4) . ? C9 C14 1.382(3) . ? C9 C10 1.387(4) . ? C10 C11 1.378(4) . ? C11 C12 1.367(4) . ? C12 C13 1.392(4) . ? C13 C14 1.373(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 C1 N1 N2 110.7(2) . . ? C1 N1 C9 129.8(2) . . ? N2 N1 C9 119.5(2) . . ? N3 N2 N1 106.4(2) . . ? N2 N3 C2 109.8(2) . . ? O1 N4 O2 124.2(2) . . ? O1 N4 C14 117.3(2) . . ? O2 N4 C14 118.4(2) . . ? N1 C1 C2 105.7(2) . . ? N3 C2 C1 107.4(2) . . ? N3 C2 C3 122.6(2) . . ? C1 C2 C3 130.0(2) . . ? C8 C3 C4 117.9(3) . . ? C8 C3 C2 121.6(3) . . ? C4 C3 C2 120.4(2) . . ? C5 C4 C3 120.8(3) . . ? C6 C5 C4 120.0(3) . . ? C5 C6 C7 120.1(3) . . ? C8 C7 C6 119.9(3) . . ? C7 C8 C3 121.2(3) . . ? C14 C9 C10 118.8(2) . . ? C14 C9 N1 121.2(2) . . ? C10 C9 N1 119.9(2) . . ? C11 C10 C9 119.4(3) . . ? C12 C11 C10 121.2(3) . . ? C11 C12 C13 120.3(3) . . ? C14 C13 C12 118.2(3) . . ? C13 C14 C9 122.0(2) . . ? C13 C14 N4 117.1(2) . . ? C9 C14 N4 120.7(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 C1 N1 N2 N3 -0.2(3) . . . . ? C9 N1 N2 N3 177.9(2) . . . . ? N1 N2 N3 C2 -0.2(3) . . . . ? N2 N1 C1 C2 0.5(3) . . . . ? C9 N1 C1 C2 -177.3(2) . . . . ? N2 N3 C2 C1 0.5(3) . . . . ? N2 N3 C2 C3 -178.0(2) . . . . ? N1 C1 C2 N3 -0.6(3) . . . . ? N1 C1 C2 C3 177.7(3) . . . . ? N3 C2 C3 C8 -158.7(3) . . . . ? C1 C2 C3 C8 23.2(4) . . . . ? N3 C2 C3 C4 23.0(4) . . . . ? C1 C2 C3 C4 -155.2(3) . . . . ? C8 C3 C4 C5 -0.1(4) . . . . ? C2 C3 C4 C5 178.3(3) . . . . ? C3 C4 C5 C6 -0.8(5) . . . . ? C4 C5 C6 C7 0.8(5) . . . . ? C5 C6 C7 C8 0.0(5) . . . . ? C6 C7 C8 C3 -0.9(5) . . . . ? C4 C3 C8 C7 0.9(4) . . . . ? C2 C3 C8 C7 -177.5(3) . . . . ? C1 N1 C9 C14 123.6(3) . . . . ? N2 N1 C9 C14 -54.1(3) . . . . ? C1 N1 C9 C10 -59.2(4) . . . . ? N2 N1 C9 C10 123.1(3) . . . . ? C14 C9 C10 C11 0.9(4) . . . . ? N1 C9 C10 C11 -176.3(2) . . . . ? C9 C10 C11 C12 1.4(5) . . . . ? C10 C11 C12 C13 -1.4(5) . . . . ? C11 C12 C13 C14 -0.9(5) . . . . ? C12 C13 C14 C9 3.3(4) . . . . ? C12 C13 C14 N4 -172.6(3) . . . . ? C10 C9 C14 C13 -3.4(4) . . . . ? N1 C9 C14 C13 173.8(2) . . . . ? C10 C9 C14 N4 172.5(2) . . . . ? N1 C9 C14 N4 -10.3(4) . . . . ? O1 N4 C14 C13 136.9(3) . . . . ? O2 N4 C14 C13 -40.4(3) . . . . ? O1 N4 C14 C9 -39.2(3) . . . . ? O2 N4 C14 C9 143.5(3) . . . . ? 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 C1 H1 O1 0.94(3) 2.47(3) 3.270(3) 143(2) 2_645 C11 H11 N2 0.97(3) 2.71(3) 3.642(4) 162(2) 1_545 C13 H13 O2 0.97(3) 2.59(3) 3.334(4) 133(2) 3_656 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.162 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.036 #===END data_9 _database_code_depnum_ccdc_archive 'CCDC 679557' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 Br N4 O2' _chemical_formula_sum 'C14 H9 Br N4 O2' _chemical_formula_weight 345.16 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 12.388(13) _cell_length_b 8.051(9) _cell_length_c 14.256(15) _cell_angle_alpha 90.00 _cell_angle_beta 103.305(18) _cell_angle_gamma 90.00 _cell_volume 1384(2) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1834 _cell_measurement_theta_min 2.95 _cell_measurement_theta_max 22.37 _exptl_crystal_description BLOCK _exptl_crystal_colour ORANGE _exptl_crystal_size_max 0.77 _exptl_crystal_size_mid 0.68 _exptl_crystal_size_min 0.54 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.657 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 2.981 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.2074 _exptl_absorpt_correction_T_max 0.2959 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6344 _diffrn_reflns_av_R_equivalents 0.0517 _diffrn_reflns_av_sigmaI/netI 0.0648 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2419 _reflns_number_gt 1685 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _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 SHELXTL _computing_publication_material 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^)+(0.0830P)^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 RIDING _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2419 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0699 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1376 _refine_ls_wR_factor_gt 0.1245 _refine_ls_goodness_of_fit_ref 0.960 _refine_ls_restrained_S_all 0.960 _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 0.78644(5) 1.01839(6) 0.43023(4) 0.0829(3) Uani 1 1 d . . . O1 O 0.6820(3) 0.8034(5) 0.8341(2) 0.0966(10) Uani 1 1 d . . . O2 O 0.5582(3) 0.8225(6) 0.9164(3) 0.1144(13) Uani 1 1 d . . . N1 N 0.5919(3) 0.9578(4) 0.6590(2) 0.0592(8) Uani 1 1 d . . . N2 N 0.5227(3) 0.8285(5) 0.6439(3) 0.0887(12) Uani 1 1 d . . . N3 N 0.5497(3) 0.7372(5) 0.5769(3) 0.0823(11) Uani 1 1 d . . . N4 N 0.6073(3) 0.8757(5) 0.8584(3) 0.0761(10) Uani 1 1 d . . . C1 C 0.6632(3) 0.9479(5) 0.6007(3) 0.0552(9) Uani 1 1 d . . . H1 H 0.7190 1.0231 0.5968 0.066 Uiso 1 1 calc R . . C2 C 0.6375(3) 0.8074(5) 0.5491(2) 0.0559(9) Uani 1 1 d . . . C3 C 0.6843(3) 0.7187(5) 0.4778(2) 0.0546(9) Uani 1 1 d . . . C4 C 0.6628(4) 0.5499(5) 0.4635(3) 0.0653(11) Uani 1 1 d . . . H4 H 0.6194 0.4973 0.4999 0.078 Uiso 1 1 calc R . . C5 C 0.7027(4) 0.4584(6) 0.3988(4) 0.0791(14) Uani 1 1 d . . . H5 H 0.6854 0.3462 0.3906 0.095 Uiso 1 1 calc R . . C6 C 0.7689(4) 0.5329(6) 0.3452(4) 0.0797(14) Uani 1 1 d . . . H6 H 0.7984 0.4704 0.3022 0.096 Uiso 1 1 calc R . . C7 C 0.7908(4) 0.6981(6) 0.3555(3) 0.0707(11) Uani 1 1 d . . . H7 H 0.8339 0.7494 0.3184 0.085 Uiso 1 1 calc R . . C8 C 0.7492(3) 0.7897(5) 0.4210(2) 0.0595(10) Uani 1 1 d . . . C9 C 0.5802(3) 1.0819(5) 0.7253(3) 0.0550(9) Uani 1 1 d . . . C10 C 0.5635(3) 1.2447(5) 0.6959(3) 0.0673(11) Uani 1 1 d . . . H10 H 0.5654 1.2735 0.6331 0.081 Uiso 1 1 calc R . . C11 C 0.5438(3) 1.3654(6) 0.7585(4) 0.0806(13) Uani 1 1 d . . . H11 H 0.5347 1.4754 0.7384 0.097 Uiso 1 1 calc R . . C12 C 0.5378(3) 1.3234(7) 0.8497(4) 0.0866(14) Uani 1 1 d . . . H12 H 0.5218 1.4047 0.8908 0.104 Uiso 1 1 calc R . . C13 C 0.5554(3) 1.1608(7) 0.8820(3) 0.0767(13) Uani 1 1 d . . . H13 H 0.5515 1.1327 0.9444 0.092 Uiso 1 1 calc R . . C14 C 0.5784(3) 1.0429(5) 0.8206(3) 0.0601(10) 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 0.1208(5) 0.0520(3) 0.0910(4) 0.0030(2) 0.0553(3) -0.0095(2) O1 0.096(2) 0.088(2) 0.115(2) 0.021(2) 0.043(2) 0.030(2) O2 0.120(3) 0.125(3) 0.112(3) 0.043(2) 0.056(2) 0.005(2) N1 0.061(2) 0.0584(19) 0.0606(19) -0.0055(16) 0.0198(16) -0.0110(16) N2 0.093(3) 0.088(3) 0.098(3) -0.028(2) 0.049(2) -0.042(2) N3 0.088(3) 0.076(3) 0.093(2) -0.025(2) 0.041(2) -0.033(2) N4 0.068(2) 0.091(3) 0.071(2) 0.018(2) 0.0191(19) 0.004(2) C1 0.059(2) 0.051(2) 0.059(2) -0.0020(18) 0.0211(18) -0.0072(18) C2 0.059(2) 0.051(2) 0.059(2) -0.0017(18) 0.0150(17) -0.0070(18) C3 0.057(2) 0.048(2) 0.055(2) -0.0024(17) 0.0053(17) -0.0016(18) C4 0.069(3) 0.050(2) 0.074(3) -0.001(2) 0.011(2) -0.0033(19) C5 0.086(3) 0.051(3) 0.094(3) -0.013(2) 0.006(3) 0.006(2) C6 0.088(3) 0.075(3) 0.074(3) -0.017(2) 0.014(3) 0.019(3) C7 0.081(3) 0.069(3) 0.063(2) -0.003(2) 0.019(2) 0.007(2) C8 0.071(2) 0.049(2) 0.060(2) 0.0041(18) 0.0166(19) 0.0043(19) C9 0.044(2) 0.063(2) 0.058(2) -0.0093(19) 0.0120(17) -0.0039(18) C10 0.065(3) 0.070(3) 0.066(2) 0.000(2) 0.0116(19) 0.001(2) C11 0.071(3) 0.066(3) 0.101(4) -0.007(3) 0.011(3) 0.011(2) C12 0.064(3) 0.095(4) 0.102(4) -0.030(3) 0.021(2) 0.010(3) C13 0.059(3) 0.110(4) 0.064(3) -0.012(3) 0.022(2) 0.006(3) C14 0.045(2) 0.071(3) 0.064(2) -0.003(2) 0.0112(18) 0.0003(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 Br1 C8 1.895(4) . ? O1 N4 1.209(4) . ? O2 N4 1.212(4) . ? N1 N2 1.334(5) . ? N1 C1 1.348(5) . ? N1 C9 1.405(5) . ? N2 N3 1.308(5) . ? N3 C2 1.363(5) . ? N4 C14 1.463(6) . ? C1 C2 1.347(5) . ? C2 C3 1.467(5) . ? C3 C8 1.388(5) . ? C3 C4 1.391(5) . ? C4 C5 1.359(6) . ? C5 C6 1.381(7) . ? C6 C7 1.358(6) . ? C7 C8 1.380(5) . ? C9 C10 1.377(6) . ? C9 C14 1.400(6) . ? C10 C11 1.378(6) . ? C11 C12 1.363(7) . ? C12 C13 1.388(7) . ? C13 C14 1.365(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 N2 N1 C1 110.0(3) . . ? N2 N1 C9 120.1(3) . . ? C1 N1 C9 129.8(3) . . ? N3 N2 N1 107.0(3) . . ? N2 N3 C2 109.6(3) . . ? O1 N4 O2 124.2(4) . . ? O1 N4 C14 118.4(4) . . ? O2 N4 C14 117.2(4) . . ? C2 C1 N1 106.3(3) . . ? C1 C2 N3 107.1(3) . . ? C1 C2 C3 134.9(4) . . ? N3 C2 C3 118.0(3) . . ? C8 C3 C4 115.7(4) . . ? C8 C3 C2 125.3(3) . . ? C4 C3 C2 119.0(4) . . ? C5 C4 C3 122.8(4) . . ? C4 C5 C6 119.7(5) . . ? C7 C6 C5 119.6(4) . . ? C6 C7 C8 120.0(4) . . ? C7 C8 C3 122.1(4) . . ? C7 C8 Br1 116.3(3) . . ? C3 C8 Br1 121.6(3) . . ? C10 C9 C14 118.3(4) . . ? C10 C9 N1 120.2(4) . . ? C14 C9 N1 121.4(4) . . ? C9 C10 C11 120.7(4) . . ? C12 C11 C10 120.0(5) . . ? C11 C12 C13 120.8(5) . . ? C14 C13 C12 118.9(4) . . ? C13 C14 C9 121.3(4) . . ? C13 C14 N4 118.3(4) . . ? C9 C14 N4 120.4(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 C5 H5 Br1 0.93 2.92 3.690(6) 141.1 1_545 C13 H13 O2 0.93 2.68 3.482(6) 145.4 3_677 C1 H1 O1 0.93 2.65 3.451(6) 145.0 2_656 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.923 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.073 #===END data_10 _database_code_depnum_ccdc_archive 'CCDC 679558' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 Br N4 O2' _chemical_formula_sum 'C14 H9 Br N4 O2' _chemical_formula_weight 345.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M 'P 21/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 9.2835(11) _cell_length_b 7.2943(9) _cell_length_c 20.794(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.444(2) _cell_angle_gamma 90.00 _cell_volume 1396.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 2171 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 22.20 _exptl_crystal_description PLATE _exptl_crystal_colour ORANGE _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.642 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 2.954 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.3142 _exptl_absorpt_correction_T_max 0.7001 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8147 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2448 _reflns_number_gt 1881 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _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 SHELXTL _computing_publication_material 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^)+(0.0449P)^2^+0.6717P] 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 RIDING _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2448 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0942 _refine_ls_wR_factor_gt 0.0876 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 -0.35384(4) 0.67164(6) 0.017641(17) 0.08172(19) Uani 1 1 d . . . O1 O 0.3640(3) 0.8414(4) 0.31455(17) 0.1016(10) Uani 1 1 d . . . O2 O 0.4556(3) 0.8569(3) 0.41448(19) 0.0994(10) Uani 1 1 d . . . N1 N 0.0863(2) 0.6940(3) 0.31547(11) 0.0459(5) Uani 1 1 d . . . N2 N 0.0615(3) 0.8586(3) 0.34212(12) 0.0540(6) Uani 1 1 d . . . N3 N -0.0251(3) 0.9486(3) 0.29872(12) 0.0544(6) Uani 1 1 d . . . N4 N 0.3809(3) 0.7831(4) 0.36969(19) 0.0671(8) Uani 1 1 d . . . C1 C 0.0155(3) 0.6812(4) 0.25556(14) 0.0493(7) Uani 1 1 d . . . H1 H 0.0148 0.5822 0.2273 0.059 Uiso 1 1 calc R . . C2 C -0.0559(3) 0.8441(4) 0.24450(13) 0.0454(6) Uani 1 1 d . . . C3 C -0.1491(3) 0.9078(4) 0.18638(14) 0.0453(6) Uani 1 1 d . . . C4 C -0.1827(3) 1.0923(4) 0.17716(16) 0.0536(7) Uani 1 1 d . . . H4 H -0.1512 1.1769 0.2094 0.064 Uiso 1 1 calc R . . C5 C -0.2632(3) 1.1503(4) 0.11997(17) 0.0615(8) Uani 1 1 d . . . H5 H -0.2838 1.2744 0.1139 0.074 Uiso 1 1 calc R . . C6 C -0.3129(3) 1.0275(5) 0.07226(16) 0.0610(8) Uani 1 1 d . . . H6 H -0.3664 1.0674 0.0339 0.073 Uiso 1 1 calc R . . C7 C -0.2821(3) 0.8436(4) 0.08212(14) 0.0543(7) Uani 1 1 d . . . C8 C -0.2015(3) 0.7824(4) 0.13845(14) 0.0500(7) Uani 1 1 d . . . H8 H -0.1823 0.6580 0.1444 0.060 Uiso 1 1 calc R . . C9 C 0.1769(3) 0.5613(4) 0.35132(13) 0.0432(6) Uani 1 1 d . . . C10 C 0.1269(3) 0.3857(4) 0.35846(15) 0.0532(7) Uani 1 1 d . . . H10 H 0.0352 0.3524 0.3384 0.064 Uiso 1 1 calc R . . C11 C 0.2115(4) 0.2590(4) 0.39510(16) 0.0600(8) Uani 1 1 d . . . H11 H 0.1773 0.1403 0.3991 0.072 Uiso 1 1 calc R . . C12 C 0.3467(4) 0.3071(4) 0.42597(15) 0.0572(8) Uani 1 1 d . . . H12 H 0.4028 0.2218 0.4514 0.069 Uiso 1 1 calc R . . C13 C 0.3981(3) 0.4816(4) 0.41901(14) 0.0539(7) Uani 1 1 d . . . H13 H 0.4889 0.5153 0.4399 0.065 Uiso 1 1 calc R . . C14 C 0.3151(3) 0.6055(4) 0.38121(14) 0.0459(7) 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 0.0835(3) 0.0949(3) 0.0606(3) -0.01076(19) -0.01375(18) -0.0102(2) O1 0.0892(19) 0.087(2) 0.131(3) 0.0560(19) 0.0243(18) -0.0121(15) O2 0.0694(16) 0.0563(15) 0.166(3) -0.0103(17) -0.0101(18) -0.0141(13) N1 0.0507(13) 0.0410(13) 0.0449(13) -0.0024(10) 0.0021(11) 0.0048(10) N2 0.0674(16) 0.0403(14) 0.0510(14) -0.0065(11) -0.0047(12) 0.0053(12) N3 0.0660(16) 0.0416(13) 0.0528(14) -0.0048(12) -0.0024(12) 0.0058(12) N4 0.0447(15) 0.0482(16) 0.109(3) 0.0113(17) 0.0106(16) -0.0014(13) C1 0.0531(17) 0.0469(16) 0.0465(16) -0.0089(13) 0.0015(13) 0.0054(13) C2 0.0496(15) 0.0416(16) 0.0449(15) -0.0023(13) 0.0054(12) 0.0021(12) C3 0.0419(15) 0.0474(16) 0.0468(15) 0.0019(13) 0.0066(12) 0.0004(12) C4 0.0497(16) 0.0488(17) 0.0622(19) -0.0001(15) 0.0067(14) 0.0068(14) C5 0.0530(18) 0.0528(19) 0.079(2) 0.0144(17) 0.0103(17) 0.0092(15) C6 0.0468(17) 0.074(2) 0.0601(19) 0.0187(18) -0.0006(15) 0.0021(16) C7 0.0439(16) 0.065(2) 0.0523(17) 0.0034(15) 0.0008(13) -0.0048(14) C8 0.0517(17) 0.0476(17) 0.0496(17) 0.0029(13) 0.0023(13) 0.0014(13) C9 0.0463(15) 0.0409(15) 0.0425(14) -0.0002(12) 0.0067(12) 0.0012(12) C10 0.0557(18) 0.0456(17) 0.0570(18) -0.0069(14) 0.0023(14) -0.0070(14) C11 0.080(2) 0.0357(15) 0.065(2) 0.0023(15) 0.0124(18) -0.0027(15) C12 0.068(2) 0.0449(17) 0.0572(19) 0.0084(14) 0.0041(16) 0.0109(15) C13 0.0492(16) 0.0528(18) 0.0580(18) 0.0003(15) 0.0010(14) 0.0041(14) C14 0.0473(16) 0.0382(14) 0.0535(17) 0.0033(13) 0.0118(13) -0.0005(12) _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 C7 1.893(3) . ? O1 N4 1.214(4) . ? O2 N4 1.213(4) . ? N1 C1 1.335(4) . ? N1 N2 1.354(3) . ? N1 C9 1.427(3) . ? N2 N3 1.306(3) . ? N3 C2 1.360(3) . ? N4 C14 1.465(4) . ? C1 C2 1.366(4) . ? C2 C3 1.467(4) . ? C3 C4 1.389(4) . ? C3 C8 1.393(4) . ? C4 C5 1.386(4) . ? C5 C6 1.372(5) . ? C6 C7 1.381(4) . ? C7 C8 1.380(4) . ? C9 C10 1.378(4) . ? C9 C14 1.389(4) . ? C10 C11 1.377(4) . ? C11 C12 1.379(5) . ? C12 C13 1.374(4) . ? C13 C14 1.368(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 C1 N1 N2 110.8(2) . . ? C1 N1 C9 128.7(2) . . ? N2 N1 C9 120.5(2) . . ? N3 N2 N1 106.6(2) . . ? N2 N3 C2 109.6(2) . . ? O2 N4 O1 124.2(3) . . ? O2 N4 C14 118.4(3) . . ? O1 N4 C14 117.3(3) . . ? N1 C1 C2 105.4(2) . . ? N3 C2 C1 107.6(2) . . ? N3 C2 C3 122.9(2) . . ? C1 C2 C3 129.4(3) . . ? C4 C3 C8 119.0(3) . . ? C4 C3 C2 121.2(3) . . ? C8 C3 C2 119.7(3) . . ? C5 C4 C3 120.1(3) . . ? C6 C5 C4 121.0(3) . . ? C5 C6 C7 118.9(3) . . ? C8 C7 C6 121.3(3) . . ? C8 C7 Br1 119.3(2) . . ? C6 C7 Br1 119.4(2) . . ? C7 C8 C3 119.7(3) . . ? C10 C9 C14 118.2(3) . . ? C10 C9 N1 120.2(3) . . ? C14 C9 N1 121.6(2) . . ? C11 C10 C9 120.5(3) . . ? C10 C11 C12 120.5(3) . . ? C13 C12 C11 119.6(3) . . ? C14 C13 C12 119.7(3) . . ? C13 C14 C9 121.5(3) . . ? C13 C14 N4 117.6(3) . . ? C9 C14 N4 120.8(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 C1 N1 N2 N3 0.0(3) . . . . ? C9 N1 N2 N3 -179.4(2) . . . . ? N1 N2 N3 C2 -0.2(3) . . . . ? N2 N1 C1 C2 0.1(3) . . . . ? C9 N1 C1 C2 179.5(2) . . . . ? N2 N3 C2 C1 0.2(3) . . . . ? N2 N3 C2 C3 -179.1(3) . . . . ? N1 C1 C2 N3 -0.2(3) . . . . ? N1 C1 C2 C3 179.0(3) . . . . ? N3 C2 C3 C4 15.9(4) . . . . ? C1 C2 C3 C4 -163.3(3) . . . . ? N3 C2 C3 C8 -166.1(3) . . . . ? C1 C2 C3 C8 14.7(4) . . . . ? C8 C3 C4 C5 -2.2(4) . . . . ? C2 C3 C4 C5 175.8(3) . . . . ? C3 C4 C5 C6 1.1(5) . . . . ? C4 C5 C6 C7 0.3(5) . . . . ? C5 C6 C7 C8 -0.7(5) . . . . ? C5 C6 C7 Br1 178.5(2) . . . . ? C6 C7 C8 C3 -0.4(4) . . . . ? Br1 C7 C8 C3 -179.6(2) . . . . ? C4 C3 C8 C7 1.8(4) . . . . ? C2 C3 C8 C7 -176.2(3) . . . . ? C1 N1 C9 C10 -52.4(4) . . . . ? N2 N1 C9 C10 126.9(3) . . . . ? C1 N1 C9 C14 129.3(3) . . . . ? N2 N1 C9 C14 -51.3(4) . . . . ? C14 C9 C10 C11 0.9(4) . . . . ? N1 C9 C10 C11 -177.4(3) . . . . ? C9 C10 C11 C12 1.0(5) . . . . ? C10 C11 C12 C13 -1.3(5) . . . . ? C11 C12 C13 C14 -0.4(5) . . . . ? C12 C13 C14 C9 2.4(4) . . . . ? C12 C13 C14 N4 -173.6(3) . . . . ? C10 C9 C14 C13 -2.6(4) . . . . ? N1 C9 C14 C13 175.7(2) . . . . ? C10 C9 C14 N4 173.2(3) . . . . ? N1 C9 C14 N4 -8.5(4) . . . . ? O2 N4 C14 C13 -40.6(4) . . . . ? O1 N4 C14 C13 134.9(3) . . . . ? O2 N4 C14 C9 143.4(3) . . . . ? O1 N4 C14 C9 -41.1(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 C1 H1 O1 0.93 2.32 3.153(4) 149.6 2_545 C11 H11 N2 0.93 2.54 3.360(4) 147.3 1_545 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.568 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.051 #===END data_11 _database_code_depnum_ccdc_archive 'CCDC 679559' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 Br N4 O2' _chemical_formula_sum 'C14 H9 Br N4 O2' _chemical_formula_weight 345.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M 'P 21/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 5.4468(9) _cell_length_b 20.778(3) _cell_length_c 12.482(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.427(3) _cell_angle_gamma 90.00 _cell_volume 1379.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 2192 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 23.75 _exptl_crystal_description NEEDLE _exptl_crystal_colour ORANGE _exptl_crystal_size_max 0.68 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.662 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 2.989 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.2357 _exptl_absorpt_correction_T_max 0.5862 _exptl_absorpt_process_details "BRUKER'S SADABS" _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6843 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0249 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 24.98 _reflns_number_total 2427 _reflns_number_gt 1896 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _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 SHELXTL _computing_publication_material 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^)+(0.0368P)^2^+0.9060P] 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 REFALL _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2427 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0889 _refine_ls_wR_factor_gt 0.0823 _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 0.09857(8) 0.460922(19) 0.89370(3) 0.07820(18) Uani 1 1 d . . . O1 O 0.2517(5) 0.24496(15) 0.2699(2) 0.0882(9) Uani 1 1 d . . . O2 O 0.4529(5) 0.23384(14) 0.1406(2) 0.0833(8) Uani 1 1 d . . . N1 N 0.0340(4) 0.36601(12) 0.24565(18) 0.0468(6) Uani 1 1 d . . . N2 N 0.2754(5) 0.38603(15) 0.2731(2) 0.0631(8) Uani 1 1 d . . . N3 N 0.3146(5) 0.40533(15) 0.3749(2) 0.0615(7) Uani 1 1 d . . . N4 N 0.2784(5) 0.25457(13) 0.1766(2) 0.0579(7) Uani 1 1 d . . . C1 C -0.0786(6) 0.37326(15) 0.3307(2) 0.0444(7) Uani 1 1 d . . . C2 C 0.1012(5) 0.39805(14) 0.4135(2) 0.0441(7) Uani 1 1 d . . . C3 C 0.0951(5) 0.41362(14) 0.5281(2) 0.0448(7) Uani 1 1 d . . . C4 C 0.2834(7) 0.45110(15) 0.5900(3) 0.0526(8) Uani 1 1 d . . . C5 C 0.2856(7) 0.46510(15) 0.6988(3) 0.0558(8) Uani 1 1 d . . . C6 C 0.0962(6) 0.44130(14) 0.7446(2) 0.0510(7) Uani 1 1 d . . . C7 C -0.0926(7) 0.40371(17) 0.6852(3) 0.0575(8) Uani 1 1 d . . . C8 C -0.0930(6) 0.39040(17) 0.5770(3) 0.0537(8) Uani 1 1 d . . . C9 C -0.0557(5) 0.33853(14) 0.1399(2) 0.0450(7) Uani 1 1 d . . . C10 C -0.2678(6) 0.36273(16) 0.0705(3) 0.0540(8) Uani 1 1 d . . . C11 C -0.3401(7) 0.33877(18) -0.0347(3) 0.0622(9) Uani 1 1 d . . . C12 C -0.1981(7) 0.29362(18) -0.0729(3) 0.0640(9) Uani 1 1 d . . . C13 C 0.0114(7) 0.26863(17) -0.0047(3) 0.0564(8) Uani 1 1 d . . . C14 C 0.0771(5) 0.28958(14) 0.1022(2) 0.0459(7) Uani 1 1 d . . . H1 H -0.233(6) 0.3620(13) 0.325(2) 0.038(7) Uiso 1 1 d . . . H4 H 0.404(6) 0.4664(14) 0.560(3) 0.053(9) Uiso 1 1 d . . . H5 H 0.414(7) 0.4931(18) 0.740(3) 0.075(11) Uiso 1 1 d . . . H7 H -0.228(7) 0.3862(18) 0.718(3) 0.083(11) Uiso 1 1 d . . . H8 H -0.214(6) 0.3651(16) 0.541(3) 0.061(10) Uiso 1 1 d . . . H10 H -0.347(6) 0.3939(15) 0.095(2) 0.049(9) Uiso 1 1 d . . . H11 H -0.483(7) 0.3549(17) -0.077(3) 0.075(11) Uiso 1 1 d . . . H12 H -0.245(7) 0.2801(17) -0.147(3) 0.080(11) Uiso 1 1 d . . . H13 H 0.109(6) 0.2364(16) -0.027(3) 0.058(9) Uiso 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 0.1102(4) 0.0781(3) 0.0546(2) -0.01816(17) 0.0359(2) -0.0037(2) O1 0.0905(19) 0.121(2) 0.0513(15) 0.0271(14) 0.0114(13) 0.0327(17) O2 0.0668(16) 0.102(2) 0.0842(18) 0.0074(15) 0.0231(14) 0.0283(15) N1 0.0380(13) 0.0619(16) 0.0410(13) -0.0051(11) 0.0095(10) -0.0064(11) N2 0.0431(15) 0.100(2) 0.0488(15) -0.0197(14) 0.0155(11) -0.0188(14) N3 0.0468(15) 0.094(2) 0.0459(14) -0.0185(14) 0.0140(12) -0.0165(14) N4 0.0549(17) 0.0620(17) 0.0544(17) 0.0028(13) 0.0061(13) 0.0047(14) C1 0.0334(16) 0.0532(18) 0.0480(16) 0.0003(13) 0.0120(13) 0.0000(14) C2 0.0392(16) 0.0501(17) 0.0443(16) -0.0014(13) 0.0116(13) 0.0006(13) C3 0.0457(17) 0.0453(16) 0.0453(16) -0.0016(13) 0.0139(13) 0.0059(13) C4 0.055(2) 0.0550(19) 0.0518(18) -0.0048(14) 0.0204(16) -0.0097(16) C5 0.066(2) 0.0532(18) 0.0492(18) -0.0125(15) 0.0143(16) -0.0072(17) C6 0.064(2) 0.0475(17) 0.0460(16) -0.0043(13) 0.0209(15) 0.0089(15) C7 0.059(2) 0.065(2) 0.0542(19) -0.0026(16) 0.0259(16) -0.0006(17) C8 0.0475(19) 0.064(2) 0.0505(18) -0.0076(15) 0.0137(15) -0.0063(16) C9 0.0425(16) 0.0527(18) 0.0388(15) -0.0009(13) 0.0067(12) -0.0076(14) C10 0.053(2) 0.052(2) 0.0554(19) 0.0001(15) 0.0065(15) 0.0029(16) C11 0.057(2) 0.065(2) 0.054(2) 0.0074(17) -0.0095(17) -0.0036(18) C12 0.078(2) 0.066(2) 0.0418(18) -0.0013(16) -0.0009(17) -0.0072(19) C13 0.066(2) 0.055(2) 0.0483(18) -0.0056(15) 0.0123(16) -0.0039(17) C14 0.0425(16) 0.0505(17) 0.0432(15) 0.0017(13) 0.0060(12) -0.0056(14) _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 C6 1.903(3) . ? O1 N4 1.220(3) . ? O2 N4 1.215(3) . ? N1 C1 1.344(4) . ? N1 N2 1.351(3) . ? N1 C9 1.425(3) . ? N2 N3 1.306(3) . ? N3 C2 1.359(4) . ? N4 C14 1.469(4) . ? C1 C2 1.362(4) . ? C2 C3 1.475(4) . ? C3 C4 1.383(4) . ? C3 C8 1.387(4) . ? C4 C5 1.386(4) . ? C5 C6 1.374(5) . ? C6 C7 1.374(5) . ? C7 C8 1.378(4) . ? C9 C10 1.381(4) . ? C9 C14 1.387(4) . ? C10 C11 1.380(5) . ? C11 C12 1.365(5) . ? C12 C13 1.370(5) . ? C13 C14 1.376(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 C1 N1 N2 110.5(2) . . ? C1 N1 C9 130.8(3) . . ? N2 N1 C9 118.6(2) . . ? N3 N2 N1 106.7(2) . . ? N2 N3 C2 109.7(2) . . ? O2 N4 O1 124.0(3) . . ? O2 N4 C14 118.6(3) . . ? O1 N4 C14 117.3(3) . . ? N1 C1 C2 105.4(3) . . ? N3 C2 C1 107.7(3) . . ? N3 C2 C3 121.2(2) . . ? C1 C2 C3 131.0(3) . . ? C4 C3 C8 118.6(3) . . ? C4 C3 C2 119.8(3) . . ? C8 C3 C2 121.6(3) . . ? C3 C4 C5 120.9(3) . . ? C6 C5 C4 118.9(3) . . ? C5 C6 C7 121.5(3) . . ? C5 C6 Br1 118.8(2) . . ? C7 C6 Br1 119.7(2) . . ? C6 C7 C8 119.0(3) . . ? C7 C8 C3 121.0(3) . . ? C10 C9 C14 118.7(3) . . ? C10 C9 N1 120.6(3) . . ? C14 C9 N1 120.5(2) . . ? C11 C10 C9 119.7(3) . . ? C12 C11 C10 120.8(3) . . ? C11 C12 C13 120.2(3) . . ? C12 C13 C14 119.3(3) . . ? C13 C14 C9 121.0(3) . . ? C13 C14 N4 117.4(3) . . ? C9 C14 N4 121.4(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 C1 N1 N2 N3 0.4(4) . . . . ? C9 N1 N2 N3 -176.2(3) . . . . ? N1 N2 N3 C2 -0.1(4) . . . . ? N2 N1 C1 C2 -0.6(3) . . . . ? C9 N1 C1 C2 175.5(3) . . . . ? N2 N3 C2 C1 -0.3(4) . . . . ? N2 N3 C2 C3 177.4(3) . . . . ? N1 C1 C2 N3 0.5(3) . . . . ? N1 C1 C2 C3 -176.9(3) . . . . ? N3 C2 C3 C4 16.8(4) . . . . ? C1 C2 C3 C4 -166.1(3) . . . . ? N3 C2 C3 C8 -161.8(3) . . . . ? C1 C2 C3 C8 15.2(5) . . . . ? C8 C3 C4 C5 0.3(5) . . . . ? C2 C3 C4 C5 -178.4(3) . . . . ? C3 C4 C5 C6 -0.3(5) . . . . ? C4 C5 C6 C7 0.6(5) . . . . ? C4 C5 C6 Br1 -179.7(2) . . . . ? C5 C6 C7 C8 -0.9(5) . . . . ? Br1 C6 C7 C8 179.4(2) . . . . ? C6 C7 C8 C3 0.8(5) . . . . ? C4 C3 C8 C7 -0.6(5) . . . . ? C2 C3 C8 C7 178.1(3) . . . . ? C1 N1 C9 C10 58.6(4) . . . . ? N2 N1 C9 C10 -125.6(3) . . . . ? C1 N1 C9 C14 -125.4(3) . . . . ? N2 N1 C9 C14 50.4(4) . . . . ? C14 C9 C10 C11 -1.2(5) . . . . ? N1 C9 C10 C11 174.9(3) . . . . ? C9 C10 C11 C12 -3.2(5) . . . . ? C10 C11 C12 C13 3.9(6) . . . . ? C11 C12 C13 C14 -0.1(5) . . . . ? C12 C13 C14 C9 -4.3(5) . . . . ? C12 C13 C14 N4 170.7(3) . . . . ? C10 C9 C14 C13 4.9(4) . . . . ? N1 C9 C14 C13 -171.2(3) . . . . ? C10 C9 C14 N4 -169.9(3) . . . . ? N1 C9 C14 N4 14.0(4) . . . . ? O2 N4 C14 C13 36.0(4) . . . . ? O1 N4 C14 C13 -139.9(3) . . . . ? O2 N4 C14 C9 -149.0(3) . . . . ? O1 N4 C14 C9 35.1(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 C1 H1 N2 0.86(3) 2.66(3) 3.447(4) 152(2) 1_455 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.657 _refine_diff_density_min -0.506 _refine_diff_density_rms 0.052 #===END data_12 _database_code_depnum_ccdc_archive 'CCDC 679560' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 N4 O2' _chemical_formula_sum 'C14 H10 N4 O2' _chemical_formula_weight 266.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 8.502(3) _cell_length_b 5.3559(18) _cell_length_c 27.363(9) _cell_angle_alpha 90.00 _cell_angle_beta 95.564(6) _cell_angle_gamma 90.00 _cell_volume 1240.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 2172 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 27.44 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9696 _exptl_absorpt_correction_T_max 0.9802 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5402 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0408 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2170 _reflns_number_gt 1779 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0564P)^2^+0.4985P] 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_number_reflns 2170 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0655 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1328 _refine_ls_wR_factor_gt 0.1260 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0029(2) 1.0378(3) 0.44121(6) 0.0626(5) Uani 1 1 d . . . O2 O 0.0521(2) 0.9861(4) 0.36626(7) 0.0679(5) Uani 1 1 d . . . N1 N 0.2947(2) 0.3584(3) 0.53720(7) 0.0434(5) Uani 1 1 d . . . N2 N 0.3655(2) 0.1365(4) 0.54893(8) 0.0573(6) Uani 1 1 d . . . N3 N 0.3657(2) 0.1069(4) 0.59611(8) 0.0573(6) Uani 1 1 d . . . N4 N 0.0679(2) 0.9265(4) 0.40952(7) 0.0464(5) Uani 1 1 d . . . C1 C 0.2507(2) 0.4711(4) 0.57811(8) 0.0421(5) Uani 1 1 d . . . H1 H 0.2004 0.6245 0.5801 0.051 Uiso 1 1 calc R . . C2 C 0.2963(2) 0.3098(4) 0.61595(8) 0.0438(5) Uani 1 1 d . . . C3 C 0.2794(2) 0.3287(4) 0.66883(8) 0.0451(5) Uani 1 1 d . . . C4 C 0.3532(3) 0.1575(5) 0.70171(10) 0.0612(7) Uani 1 1 d . . . H4 H 0.4150 0.0316 0.6901 0.073 Uiso 1 1 calc R . . C5 C 0.3365(4) 0.1709(6) 0.75107(10) 0.0730(8) Uani 1 1 d . . . H5 H 0.3870 0.0548 0.7724 0.088 Uiso 1 1 calc R . . C6 C 0.2456(3) 0.3548(6) 0.76895(10) 0.0671(7) Uani 1 1 d . . . H6 H 0.2339 0.3632 0.8024 0.081 Uiso 1 1 calc R . . C7 C 0.1716(3) 0.5273(6) 0.73707(10) 0.0693(8) Uani 1 1 d . . . H7 H 0.1101 0.6526 0.7491 0.083 Uiso 1 1 calc R . . C8 C 0.1885(3) 0.5148(5) 0.68750(10) 0.0614(7) Uani 1 1 d . . . H8 H 0.1384 0.6322 0.6663 0.074 Uiso 1 1 calc R . . C9 C 0.2794(2) 0.4419(4) 0.48744(8) 0.0403(5) Uani 1 1 d . . . C10 C 0.3627(2) 0.3174(4) 0.45310(9) 0.0474(6) Uani 1 1 d . . . H10 H 0.4283 0.1836 0.4628 0.057 Uiso 1 1 calc R . . C11 C 0.3468(3) 0.3946(5) 0.40495(9) 0.0527(6) Uani 1 1 d . . . H11 H 0.4023 0.3118 0.3822 0.063 Uiso 1 1 calc R . . C12 C 0.2501(3) 0.5929(5) 0.38968(8) 0.0496(6) Uani 1 1 d . . . H12 H 0.2392 0.6438 0.3570 0.060 Uiso 1 1 calc R . . C13 C 0.1700(2) 0.7130(4) 0.42458(8) 0.0403(5) Uani 1 1 d . . . C14 C 0.1825(2) 0.6417(4) 0.47330(8) 0.0413(5) Uani 1 1 d . . . H14 H 0.1273 0.7259 0.4960 0.050 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0678(11) 0.0604(11) 0.0605(11) -0.0035(9) 0.0108(8) 0.0239(9) O2 0.0785(12) 0.0732(13) 0.0518(11) 0.0149(9) 0.0061(9) 0.0130(10) N1 0.0439(10) 0.0358(10) 0.0503(12) -0.0029(8) 0.0043(8) 0.0077(8) N2 0.0692(13) 0.0461(12) 0.0568(14) -0.0006(10) 0.0073(10) 0.0208(10) N3 0.0709(13) 0.0457(11) 0.0554(13) 0.0013(10) 0.0068(10) 0.0178(10) N4 0.0449(10) 0.0450(11) 0.0491(12) 0.0010(9) 0.0035(9) 0.0010(8) C1 0.0441(11) 0.0344(11) 0.0475(13) -0.0066(10) 0.0031(9) 0.0039(9) C2 0.0411(11) 0.0385(11) 0.0515(14) -0.0033(10) 0.0025(9) 0.0028(9) C3 0.0429(11) 0.0413(12) 0.0505(14) -0.0004(10) 0.0018(10) -0.0034(9) C4 0.0702(16) 0.0551(15) 0.0582(17) 0.0031(12) 0.0053(12) 0.0142(13) C5 0.092(2) 0.0701(19) 0.0560(18) 0.0119(14) 0.0023(14) 0.0126(16) C6 0.0759(18) 0.0753(19) 0.0502(16) 0.0002(14) 0.0060(13) -0.0019(15) C7 0.0761(18) 0.0736(19) 0.0589(17) -0.0132(15) 0.0109(13) 0.0144(15) C8 0.0694(16) 0.0559(15) 0.0577(16) -0.0007(12) -0.0005(12) 0.0161(13) C9 0.0368(10) 0.0380(11) 0.0454(13) -0.0062(10) 0.0005(9) 0.0001(9) C10 0.0413(11) 0.0451(13) 0.0554(15) -0.0093(11) 0.0033(10) 0.0058(10) C11 0.0489(13) 0.0575(15) 0.0530(15) -0.0163(12) 0.0119(10) 0.0067(11) C12 0.0520(13) 0.0551(14) 0.0425(13) -0.0070(11) 0.0079(10) -0.0011(11) C13 0.0349(10) 0.0401(11) 0.0456(13) -0.0032(10) 0.0022(9) -0.0002(9) C14 0.0381(10) 0.0415(12) 0.0449(13) -0.0083(10) 0.0067(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 O1 N4 1.227(2) . ? O2 N4 1.221(2) . ? N1 C1 1.356(3) . ? N1 N2 1.357(3) . ? N1 C9 1.427(3) . ? N2 N3 1.300(3) . ? N3 C2 1.373(3) . ? N4 C13 1.471(3) . ? C1 C2 1.375(3) . ? C2 C3 1.471(3) . ? C3 C8 1.389(3) . ? C3 C4 1.391(3) . ? C4 C5 1.374(4) . ? C5 C6 1.371(4) . ? C6 C7 1.380(4) . ? C7 C8 1.379(4) . ? C9 C14 1.383(3) . ? C9 C10 1.399(3) . ? C10 C11 1.375(3) . ? C11 C12 1.383(3) . ? C12 C13 1.384(3) . ? C13 C14 1.381(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 N1 N2 110.26(18) . . ? C1 N1 C9 129.89(18) . . ? N2 N1 C9 119.84(17) . . ? N3 N2 N1 107.42(18) . . ? N2 N3 C2 109.69(19) . . ? O2 N4 O1 122.9(2) . . ? O2 N4 C13 118.79(18) . . ? O1 N4 C13 118.28(19) . . ? N1 C1 C2 105.18(19) . . ? N3 C2 C1 107.45(19) . . ? N3 C2 C3 122.0(2) . . ? C1 C2 C3 130.5(2) . . ? C8 C3 C4 117.9(2) . . ? C8 C3 C2 121.5(2) . . ? C4 C3 C2 120.7(2) . . ? C5 C4 C3 121.2(2) . . ? C6 C5 C4 120.3(3) . . ? C5 C6 C7 119.6(3) . . ? C8 C7 C6 120.3(3) . . ? C7 C8 C3 120.7(2) . . ? C14 C9 C10 120.5(2) . . ? C14 C9 N1 120.41(18) . . ? C10 C9 N1 119.08(19) . . ? C11 C10 C9 119.4(2) . . ? C10 C11 C12 121.4(2) . . ? C11 C12 C13 117.8(2) . . ? C14 C13 C12 122.7(2) . . ? C14 C13 N4 118.28(18) . . ? C12 C13 N4 119.0(2) . . ? C13 C14 C9 118.17(19) . . ? 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 C1 N1 N2 N3 0.5(2) . . . . ? C9 N1 N2 N3 179.24(18) . . . . ? N1 N2 N3 C2 -0.5(3) . . . . ? N2 N1 C1 C2 -0.3(2) . . . . ? C9 N1 C1 C2 -178.86(19) . . . . ? N2 N3 C2 C1 0.3(3) . . . . ? N2 N3 C2 C3 179.92(19) . . . . ? N1 C1 C2 N3 0.0(2) . . . . ? N1 C1 C2 C3 -179.6(2) . . . . ? N3 C2 C3 C8 -170.1(2) . . . . ? C1 C2 C3 C8 9.4(4) . . . . ? N3 C2 C3 C4 9.1(3) . . . . ? C1 C2 C3 C4 -171.4(2) . . . . ? C8 C3 C4 C5 0.2(4) . . . . ? C2 C3 C4 C5 -179.0(2) . . . . ? C3 C4 C5 C6 0.1(4) . . . . ? C4 C5 C6 C7 -0.3(4) . . . . ? C5 C6 C7 C8 0.2(4) . . . . ? C6 C7 C8 C3 0.2(4) . . . . ? C4 C3 C8 C7 -0.4(4) . . . . ? C2 C3 C8 C7 178.8(2) . . . . ? C1 N1 C9 C14 -13.8(3) . . . . ? N2 N1 C9 C14 167.76(19) . . . . ? C1 N1 C9 C10 166.8(2) . . . . ? N2 N1 C9 C10 -11.7(3) . . . . ? C14 C9 C10 C11 -0.3(3) . . . . ? N1 C9 C10 C11 179.08(19) . . . . ? C9 C10 C11 C12 0.0(3) . . . . ? C10 C11 C12 C13 0.4(3) . . . . ? C11 C12 C13 C14 -0.4(3) . . . . ? C11 C12 C13 N4 179.20(19) . . . . ? O2 N4 C13 C14 -177.73(19) . . . . ? O1 N4 C13 C14 2.6(3) . . . . ? O2 N4 C13 C12 2.7(3) . . . . ? O1 N4 C13 C12 -176.9(2) . . . . ? C12 C13 C14 C9 0.0(3) . . . . ? N4 C13 C14 C9 -179.58(18) . . . . ? C10 C9 C14 C13 0.4(3) . . . . ? N1 C9 C14 C13 -179.05(18) . . . . ? 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 C1 H1 O1 0.93 2.53 3.409(3) 157.6 3_576 C14 H14 O1 0.93 2.48 3.408(3) 176.2 3_576 C8 H8 O2 0.93 2.70 3.593(3) 160.1 3_576 C6 H6 O2 0.93 2.57 3.372(3) 144.2 4_576 C10 H10 N2 0.93 2.50 3.358(3) 154.4 3_656 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.171 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.038 #===END data_13 _database_code_depnum_ccdc_archive 'CCDC 679561' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 Br N4 O2' _chemical_formula_sum 'C14 H9 Br N4 O2' _chemical_formula_weight 345.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 7.228(7) _cell_length_b 13.308(13) _cell_length_c 14.521(15) _cell_angle_alpha 90.00 _cell_angle_beta 93.675(19) _cell_angle_gamma 90.00 _cell_volume 1394(2) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1537 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 19.18 _exptl_crystal_description 'thin needle' _exptl_crystal_colour ornage _exptl_crystal_size_max 0.76 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 2.959 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2120 _exptl_absorpt_correction_T_max 0.8518 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9670 _diffrn_reflns_av_R_equivalents 0.0571 _diffrn_reflns_av_sigmaI/netI 0.0538 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2455 _reflns_number_gt 1522 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _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 SHELXTL _computing_publication_material 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^)+(0.1525P)^2^+25.1020P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2455 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1755 _refine_ls_R_factor_gt 0.1357 _refine_ls_wR_factor_ref 0.4175 _refine_ls_wR_factor_gt 0.3958 _refine_ls_goodness_of_fit_ref 1.141 _refine_ls_restrained_S_all 1.141 _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 1.1266(3) 0.89950(16) 0.35563(13) 0.0868(10) Uani 1 1 d . . . O1 O 0.557(2) 1.1992(11) -0.1824(8) 0.084(4) Uani 1 1 d . . . O2 O 0.566(2) 1.3534(12) -0.1436(9) 0.098(5) Uani 1 1 d . . . N1 N 0.8338(16) 1.0121(9) 0.0898(7) 0.046(3) Uani 1 1 d . . . N2 N 0.760(2) 0.9408(11) 0.0332(9) 0.073(4) Uani 1 1 d . . . N3 N 0.797(2) 0.8547(11) 0.0711(10) 0.076(5) Uani 1 1 d . . . N4 N 0.600(2) 1.2663(12) -0.1288(9) 0.065(4) Uani 1 1 d . . . C1 C 0.916(2) 0.9677(12) 0.1646(10) 0.057(4) Uani 1 1 d . . . H1 H 0.9757 1.0001 0.2149 0.069 Uiso 1 1 calc R . . C2 C 0.898(2) 0.8693(12) 0.1539(10) 0.054(4) Uani 1 1 d . . . C3 C 0.958(2) 0.7779(12) 0.2068(11) 0.057(4) Uani 1 1 d . . . C4 C 0.916(3) 0.6844(13) 0.1694(13) 0.070(5) Uani 1 1 d . . . H4 H 0.8520 0.6805 0.1119 0.084 Uiso 1 1 calc R . . C5 C 0.968(3) 0.5947(15) 0.2162(16) 0.084(6) Uani 1 1 d . . . H5 H 0.9323 0.5330 0.1908 0.100 Uiso 1 1 calc R . . C6 C 1.068(3) 0.5986(19) 0.2973(17) 0.094(7) Uani 1 1 d . . . H6 H 1.1106 0.5396 0.3257 0.113 Uiso 1 1 calc R . . C7 C 1.108(3) 0.6921(18) 0.3392(14) 0.087(6) Uani 1 1 d . . . H7 H 1.1692 0.6954 0.3974 0.104 Uiso 1 1 calc R . . C8 C 1.055(2) 0.7773(13) 0.2936(11) 0.062(4) Uani 1 1 d . . . C9 C 0.811(2) 1.1167(12) 0.0654(10) 0.052(4) Uani 1 1 d . . . C10 C 0.887(2) 1.1892(13) 0.1246(11) 0.066(5) Uani 1 1 d . . . H10 H 0.9516 1.1711 0.1796 0.079 Uiso 1 1 calc R . . C11 C 0.866(3) 1.2886(14) 0.1005(11) 0.069(5) Uani 1 1 d . . . H11 H 0.9137 1.3382 0.1404 0.083 Uiso 1 1 calc R . . C12 C 0.772(2) 1.3166(13) 0.0157(11) 0.063(4) Uani 1 1 d . . . H12 H 0.7607 1.3835 -0.0021 0.076 Uiso 1 1 calc R . . C13 C 0.700(2) 1.2408(12) -0.0388(9) 0.053(4) Uani 1 1 d . . . C14 C 0.718(2) 1.1411(13) -0.0173(10) 0.054(4) Uani 1 1 d . . . H14 H 0.6696 1.0917 -0.0571 0.065 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 0.1128(19) 0.0814(15) 0.0616(12) 0.0131(10) -0.0309(11) -0.0123(12) O1 0.110(11) 0.095(10) 0.042(6) 0.001(6) -0.034(7) 0.000(8) O2 0.120(12) 0.090(11) 0.078(9) 0.032(8) -0.032(8) 0.008(9) N1 0.054(7) 0.048(7) 0.034(6) 0.002(5) -0.003(5) -0.002(6) N2 0.111(12) 0.062(9) 0.042(7) -0.002(7) -0.019(8) -0.002(8) N3 0.118(13) 0.048(8) 0.057(8) 0.000(7) -0.034(9) 0.002(8) N4 0.074(10) 0.076(11) 0.045(8) 0.023(8) -0.001(7) 0.020(8) C1 0.078(11) 0.058(10) 0.035(7) -0.001(7) -0.015(7) 0.005(8) C2 0.057(10) 0.059(10) 0.044(8) -0.005(7) -0.003(7) -0.001(8) C3 0.056(10) 0.051(10) 0.062(10) 0.008(8) -0.010(8) 0.003(8) C4 0.088(13) 0.057(11) 0.065(11) 0.007(9) 0.003(9) 0.009(9) C5 0.101(16) 0.060(12) 0.094(15) 0.000(11) 0.030(13) 0.000(11) C6 0.089(15) 0.100(18) 0.095(16) 0.038(14) 0.012(13) 0.040(14) C7 0.100(16) 0.089(16) 0.070(12) 0.023(11) -0.003(11) -0.011(13) C8 0.066(11) 0.065(11) 0.056(9) 0.017(8) 0.006(8) 0.006(9) C9 0.056(9) 0.059(10) 0.039(7) -0.007(7) -0.012(7) -0.003(7) C10 0.087(13) 0.060(11) 0.047(9) 0.002(7) -0.025(8) 0.013(9) C11 0.089(13) 0.062(11) 0.052(9) -0.006(8) -0.023(9) -0.004(10) C12 0.083(12) 0.052(9) 0.055(9) 0.012(8) 0.002(9) -0.003(9) C13 0.062(10) 0.060(10) 0.035(7) 0.007(7) -0.009(7) 0.001(8) C14 0.062(10) 0.062(10) 0.037(7) 0.002(7) -0.004(7) -0.003(8) _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 1.913(18) . ? O1 N4 1.211(19) . ? O2 N4 1.20(2) . ? N1 N2 1.341(17) . ? N1 C1 1.343(18) . ? N1 C9 1.443(19) . ? N2 N3 1.29(2) . ? N3 C2 1.379(19) . ? N4 C13 1.493(18) . ? C1 C2 1.32(2) . ? C2 C3 1.49(2) . ? C3 C4 1.38(2) . ? C3 C8 1.41(2) . ? C4 C5 1.41(3) . ? C5 C6 1.34(3) . ? C6 C7 1.41(3) . ? C7 C8 1.35(3) . ? C9 C14 1.37(2) . ? C9 C10 1.38(2) . ? C10 C11 1.37(2) . ? C11 C12 1.42(2) . ? C12 C13 1.36(2) . ? C13 C14 1.37(2) . ? 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 N2 N1 C1 108.7(12) . . ? N2 N1 C9 119.8(11) . . ? C1 N1 C9 131.4(12) . . ? N3 N2 N1 107.8(12) . . ? N2 N3 C2 109.2(14) . . ? O2 N4 O1 123.7(15) . . ? O2 N4 C13 117.2(16) . . ? O1 N4 C13 119.1(14) . . ? C2 C1 N1 107.7(13) . . ? C1 C2 N3 106.5(14) . . ? C1 C2 C3 136.4(14) . . ? N3 C2 C3 117.1(14) . . ? C4 C3 C8 115.5(15) . . ? C4 C3 C2 119.0(14) . . ? C8 C3 C2 125.5(15) . . ? C3 C4 C5 121.9(18) . . ? C6 C5 C4 120(2) . . ? C5 C6 C7 119.8(19) . . ? C8 C7 C6 119.1(19) . . ? C7 C8 C3 123.5(18) . . ? C7 C8 Br1 115.0(14) . . ? C3 C8 Br1 121.5(12) . . ? C14 C9 C10 122.0(15) . . ? C14 C9 N1 119.0(13) . . ? C10 C9 N1 119.0(13) . . ? C11 C10 C9 118.6(14) . . ? C10 C11 C12 120.9(15) . . ? C13 C12 C11 117.0(15) . . ? C12 C13 C14 123.9(14) . . ? C12 C13 N4 119.1(14) . . ? C14 C13 N4 116.9(14) . . ? C13 C14 C9 117.5(15) . . ? 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 C1 N1 N2 N3 0(2) . . . . ? C9 N1 N2 N3 -178.7(14) . . . . ? N1 N2 N3 C2 -1(2) . . . . ? N2 N1 C1 C2 1.3(19) . . . . ? C9 N1 C1 C2 179.3(15) . . . . ? N1 C1 C2 N3 -2(2) . . . . ? N1 C1 C2 C3 178.1(18) . . . . ? N2 N3 C2 C1 1(2) . . . . ? N2 N3 C2 C3 -178.4(15) . . . . ? C1 C2 C3 C4 -177(2) . . . . ? N3 C2 C3 C4 2(2) . . . . ? C1 C2 C3 C8 3(3) . . . . ? N3 C2 C3 C8 -177.6(17) . . . . ? C8 C3 C4 C5 0(3) . . . . ? C2 C3 C4 C5 -179.7(17) . . . . ? C3 C4 C5 C6 -3(3) . . . . ? C4 C5 C6 C7 5(3) . . . . ? C5 C6 C7 C8 -5(3) . . . . ? C6 C7 C8 C3 2(3) . . . . ? C6 C7 C8 Br1 -177.6(16) . . . . ? C4 C3 C8 C7 0(3) . . . . ? C2 C3 C8 C7 -179.7(18) . . . . ? C4 C3 C8 Br1 179.6(13) . . . . ? C2 C3 C8 Br1 0(2) . . . . ? N2 N1 C9 C14 -2(2) . . . . ? C1 N1 C9 C14 -179.9(16) . . . . ? N2 N1 C9 C10 179.9(16) . . . . ? C1 N1 C9 C10 2(3) . . . . ? C14 C9 C10 C11 1(3) . . . . ? N1 C9 C10 C11 179.4(16) . . . . ? C9 C10 C11 C12 -2(3) . . . . ? C10 C11 C12 C13 2(3) . . . . ? C11 C12 C13 C14 -2(3) . . . . ? C11 C12 C13 N4 179.8(15) . . . . ? O2 N4 C13 C12 -9(2) . . . . ? O1 N4 C13 C12 170.6(17) . . . . ? O2 N4 C13 C14 172.2(16) . . . . ? O1 N4 C13 C14 -8(2) . . . . ? C12 C13 C14 C9 2(3) . . . . ? N4 C13 C14 C9 179.9(14) . . . . ? C10 C9 C14 C13 -1(3) . . . . ? N1 C9 C14 C13 -179.3(14) . . . . ? 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 C7 H7 N3 0.93 2.71 3.61(2) 161.3 4_676 C10 H10 O2 0.93 2.67 3.57(2) 165.0 4_686 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.445 _refine_diff_density_min -0.631 _refine_diff_density_rms 0.188 #===END data_14 _database_code_depnum_ccdc_archive 'CCDC 679562' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 Br N4 O2' _chemical_formula_sum 'C14 H9 Br N4 O2' _chemical_formula_weight 345.16 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 7.4402(6) _cell_length_b 12.4535(10) _cell_length_c 14.6016(12) _cell_angle_alpha 91.2720(10) _cell_angle_beta 98.9940(10) _cell_angle_gamma 96.3090(10) _cell_volume 1327.14(19) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 3070 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 22.83 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.727 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 3.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4270 _exptl_absorpt_correction_T_max 0.7673 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12926 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0337 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4654 _reflns_number_gt 3565 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _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 SHELXTL _computing_publication_material 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^)+(0.0437P)^2^+0.1079P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4654 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0847 _refine_ls_wR_factor_gt 0.0785 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.002 _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 0.92978(5) 0.14785(3) 1.41562(2) 0.06378(13) Uani 1 1 d . . . N1 N 0.7855(3) 0.06145(17) 0.90669(15) 0.0416(5) Uani 1 1 d . . . N2 N 0.8915(4) 0.15037(19) 0.94790(17) 0.0542(7) Uani 1 1 d . . . N3 N 0.8994(4) 0.1414(2) 1.03725(17) 0.0555(7) Uani 1 1 d . . . N4 N 0.5601(3) -0.1641(2) 0.62607(18) 0.0527(6) Uani 1 1 d . . . O1 O 0.5054(3) -0.23470(17) 0.67432(16) 0.0698(6) Uani 1 1 d . . . O2 O 0.5451(4) -0.1736(2) 0.54156(17) 0.0807(7) Uani 1 1 d . . . C1 C 0.7270(4) -0.0028(2) 0.97081(19) 0.0447(7) Uani 1 1 d . . . H1 H 0.6524 -0.0683 0.9604 0.054 Uiso 1 1 calc R . . C2 C 0.7991(4) 0.0474(2) 1.05452(19) 0.0424(7) Uani 1 1 d . . . C3 C 0.7835(4) 0.0136(2) 1.14885(19) 0.0424(7) Uani 1 1 d . . . C4 C 0.7112(4) -0.0917(2) 1.1636(2) 0.0530(8) Uani 1 1 d . . . H4 H 0.6687 -0.1399 1.1134 0.064 Uiso 1 1 calc R . . C5 C 0.7028(4) -0.1241(3) 1.2530(2) 0.0583(8) Uani 1 1 d . . . H5 H 0.6532 -0.1942 1.2622 0.070 Uiso 1 1 calc R . . C6 C 0.7667(4) -0.0545(3) 1.3287(2) 0.0569(8) Uani 1 1 d . . . H6 H 0.7622 -0.0773 1.3886 0.068 Uiso 1 1 calc R . . C7 C 0.8371(4) 0.0490(2) 1.31376(19) 0.0482(7) Uani 1 1 d . . . C8 C 0.8457(4) 0.0843(2) 1.22476(19) 0.0461(7) Uani 1 1 d . . . H8 H 0.8929 0.1550 1.2161 0.055 Uiso 1 1 calc R . . C9 C 0.7548(4) 0.0469(2) 0.80784(18) 0.0400(6) Uani 1 1 d . . . C10 C 0.8066(4) 0.1312(2) 0.7547(2) 0.0504(7) Uani 1 1 d . . . H10 H 0.8587 0.1973 0.7832 0.060 Uiso 1 1 calc R . . C11 C 0.7813(4) 0.1180(2) 0.6590(2) 0.0549(8) Uani 1 1 d . . . H11 H 0.8188 0.1748 0.6235 0.066 Uiso 1 1 calc R . . C12 C 0.7011(4) 0.0214(2) 0.6163(2) 0.0488(7) Uani 1 1 d . . . H12 H 0.6830 0.0117 0.5521 0.059 Uiso 1 1 calc R . . C13 C 0.6484(4) -0.0603(2) 0.67122(19) 0.0411(6) Uani 1 1 d . . . C14 C 0.6732(4) -0.0511(2) 0.76674(19) 0.0433(7) Uani 1 1 d . . . H14 H 0.6366 -0.1084 0.8020 0.052 Uiso 1 1 calc R . . Br1' Br 0.15469(5) 0.34673(3) 0.17677(2) 0.05838(12) Uani 1 1 d . . . O1' O 0.4704(3) 0.75528(18) 0.91475(17) 0.0750(7) Uani 1 1 d . . . O2' O 0.4251(4) 0.6924(2) 1.04611(17) 0.0841(8) Uani 1 1 d . . . N1' N 0.2094(3) 0.45830(18) 0.67869(14) 0.0402(5) Uani 1 1 d . . . N2' N 0.1364(4) 0.35989(19) 0.63845(17) 0.0540(7) Uani 1 1 d . . . N3' N 0.1432(4) 0.36546(19) 0.55021(17) 0.0544(7) Uani 1 1 d . . . N4' N 0.4116(4) 0.6848(2) 0.96165(19) 0.0555(7) Uani 1 1 d . . . C1' C 0.2621(4) 0.5246(2) 0.61428(18) 0.0441(7) Uani 1 1 d . . . H1' H 0.3157 0.5958 0.6237 0.053 Uiso 1 1 calc R . . C2' C 0.2211(4) 0.4662(2) 0.53211(18) 0.0412(6) Uani 1 1 d . . . C3' C 0.2521(4) 0.4954(2) 0.43892(19) 0.0421(6) Uani 1 1 d . . . C4' C 0.3368(4) 0.5970(2) 0.4237(2) 0.0491(7) Uani 1 1 d . . . H4' H 0.3724 0.6475 0.4729 0.059 Uiso 1 1 calc R . . C5' C 0.3684(4) 0.6234(3) 0.3361(2) 0.0549(8) Uani 1 1 d . . . H5' H 0.4266 0.6915 0.3270 0.066 Uiso 1 1 calc R . . C6' C 0.3154(4) 0.5509(3) 0.2614(2) 0.0514(8) Uani 1 1 d . . . H6' H 0.3354 0.5693 0.2022 0.062 Uiso 1 1 calc R . . C7' C 0.2317(4) 0.4501(2) 0.27730(19) 0.0445(7) Uani 1 1 d . . . C8' C 0.2000(4) 0.4213(2) 0.36454(18) 0.0431(7) Uani 1 1 d . . . H8' H 0.1442 0.3526 0.3735 0.052 Uiso 1 1 calc R . . C9' C 0.2234(4) 0.4759(2) 0.77687(18) 0.0408(6) Uani 1 1 d . . . C10' C 0.1478(4) 0.3952(2) 0.8276(2) 0.0542(8) Uani 1 1 d . . . H10' H 0.0902 0.3309 0.7979 0.065 Uiso 1 1 calc R . . C11' C 0.1575(5) 0.4100(3) 0.9222(2) 0.0616(9) Uani 1 1 d . . . H11' H 0.1064 0.3558 0.9563 0.074 Uiso 1 1 calc R . . C12' C 0.2433(4) 0.5054(3) 0.9662(2) 0.0552(8) Uani 1 1 d . . . H12' H 0.2498 0.5166 1.0298 0.066 Uiso 1 1 calc R . . C13' C 0.3182(4) 0.5829(2) 0.91445(19) 0.0436(7) Uani 1 1 d . . . C14' C 0.3108(4) 0.5717(2) 0.81978(19) 0.0426(7) Uani 1 1 d . . . H14' H 0.3623 0.6263 0.7862 0.051 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 0.0746(2) 0.0754(3) 0.03967(19) -0.00511(16) 0.01179(15) -0.00119(18) N1 0.0483(14) 0.0360(13) 0.0379(13) -0.0018(10) 0.0056(10) -0.0046(11) N2 0.0700(17) 0.0435(15) 0.0453(15) -0.0048(12) 0.0115(13) -0.0126(13) N3 0.0692(17) 0.0475(15) 0.0455(15) -0.0066(12) 0.0100(13) -0.0116(13) N4 0.0557(16) 0.0512(16) 0.0464(16) -0.0049(13) -0.0022(12) 0.0017(13) O1 0.0931(17) 0.0443(13) 0.0625(15) 0.0058(11) -0.0034(13) -0.0120(12) O2 0.109(2) 0.0729(17) 0.0499(15) -0.0141(12) 0.0030(13) -0.0189(14) C1 0.0494(17) 0.0363(16) 0.0458(17) 0.0001(13) 0.0079(13) -0.0066(13) C2 0.0441(16) 0.0396(16) 0.0429(16) -0.0020(13) 0.0085(13) 0.0005(13) C3 0.0383(15) 0.0447(17) 0.0426(16) 0.0003(13) 0.0054(12) -0.0002(13) C4 0.0546(18) 0.0491(19) 0.0526(19) 0.0018(15) 0.0067(14) -0.0033(15) C5 0.058(2) 0.0499(19) 0.066(2) 0.0053(17) 0.0133(16) -0.0050(15) C6 0.0558(19) 0.065(2) 0.0518(19) 0.0136(17) 0.0140(15) 0.0043(16) C7 0.0478(17) 0.0559(19) 0.0399(17) 0.0025(14) 0.0074(13) 0.0014(14) C8 0.0461(16) 0.0434(17) 0.0471(17) -0.0002(14) 0.0093(13) -0.0039(13) C9 0.0400(15) 0.0389(16) 0.0400(16) -0.0018(12) 0.0062(12) 0.0008(12) C10 0.0574(19) 0.0376(16) 0.0536(19) 0.0009(14) 0.0097(14) -0.0074(14) C11 0.070(2) 0.0497(19) 0.0457(18) 0.0111(15) 0.0174(15) -0.0049(16) C12 0.0522(18) 0.0574(19) 0.0358(16) 0.0023(14) 0.0063(13) 0.0025(15) C13 0.0441(16) 0.0376(16) 0.0398(16) -0.0018(13) 0.0019(12) 0.0049(13) C14 0.0467(16) 0.0377(16) 0.0442(16) 0.0049(13) 0.0057(13) 0.0008(13) Br1' 0.0737(2) 0.0643(2) 0.03626(18) -0.00251(15) 0.00844(15) 0.00530(17) O1' 0.0969(18) 0.0511(14) 0.0748(17) -0.0140(13) 0.0290(14) -0.0200(13) O2' 0.116(2) 0.0752(17) 0.0521(15) -0.0174(13) 0.0038(14) -0.0098(15) N1' 0.0476(13) 0.0374(13) 0.0335(12) 0.0004(10) 0.0064(10) -0.0041(10) N2' 0.0752(18) 0.0420(14) 0.0405(14) -0.0008(11) 0.0079(12) -0.0101(13) N3' 0.0778(18) 0.0421(14) 0.0395(14) -0.0023(11) 0.0092(12) -0.0093(13) N4' 0.0632(17) 0.0531(17) 0.0494(17) -0.0097(14) 0.0107(13) 0.0031(13) C1' 0.0517(17) 0.0389(16) 0.0400(16) 0.0016(13) 0.0090(13) -0.0045(13) C2' 0.0447(16) 0.0403(16) 0.0368(15) 0.0009(12) 0.0042(12) -0.0001(13) C3' 0.0430(16) 0.0437(16) 0.0392(16) 0.0035(13) 0.0065(12) 0.0031(13) C4' 0.0553(18) 0.0427(17) 0.0482(18) 0.0010(14) 0.0110(14) -0.0024(14) C5' 0.062(2) 0.0465(18) 0.056(2) 0.0107(15) 0.0155(16) -0.0019(15) C6' 0.0539(18) 0.060(2) 0.0420(17) 0.0140(15) 0.0111(14) 0.0074(15) C7' 0.0485(17) 0.0455(17) 0.0393(16) 0.0015(13) 0.0072(13) 0.0048(14) C8' 0.0496(17) 0.0416(16) 0.0377(15) 0.0021(13) 0.0093(12) -0.0002(13) C9' 0.0428(15) 0.0413(16) 0.0370(15) 0.0009(12) 0.0064(12) -0.0007(13) C10' 0.064(2) 0.0475(18) 0.0464(18) 0.0027(14) 0.0080(15) -0.0140(15) C11' 0.083(2) 0.057(2) 0.0412(18) 0.0105(15) 0.0146(16) -0.0162(17) C12' 0.068(2) 0.060(2) 0.0349(16) 0.0004(15) 0.0074(14) -0.0018(17) C13' 0.0441(16) 0.0434(17) 0.0412(16) -0.0052(13) 0.0059(13) -0.0019(13) C14' 0.0434(16) 0.0405(16) 0.0440(17) 0.0039(13) 0.0102(13) -0.0003(13) _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 C7 1.901(3) . ? N1 C1 1.338(3) . ? N1 N2 1.357(3) . ? N1 C9 1.430(3) . ? N2 N3 1.305(3) . ? N3 C2 1.368(4) . ? N4 O1 1.214(3) . ? N4 O2 1.223(3) . ? N4 C13 1.475(4) . ? C1 C2 1.364(4) . ? C2 C3 1.467(4) . ? C3 C8 1.387(4) . ? C3 C4 1.396(4) . ? C4 C5 1.384(4) . ? C5 C6 1.379(4) . ? C6 C7 1.373(4) . ? C7 C8 1.390(4) . ? C9 C10 1.376(4) . ? C9 C14 1.381(4) . ? C10 C11 1.384(4) . ? C11 C12 1.373(4) . ? C12 C13 1.370(4) . ? C13 C14 1.379(4) . ? Br1' C7' 1.906(3) . ? O1' N4' 1.211(3) . ? O2' N4' 1.222(3) . ? N1' C1' 1.341(3) . ? N1' N2' 1.365(3) . ? N1' C9' 1.431(3) . ? N2' N3' 1.300(3) . ? N3' C2' 1.372(3) . ? N4' C13' 1.479(4) . ? C1' C2' 1.364(4) . ? C2' C3' 1.462(4) . ? C3' C8' 1.388(4) . ? C3' C4' 1.390(4) . ? C4' C5' 1.377(4) . ? C5' C6' 1.380(4) . ? C6' C7' 1.379(4) . ? C7' C8' 1.380(4) . ? C9' C14' 1.381(4) . ? C9' C10' 1.383(4) . ? C10' C11' 1.379(4) . ? C11' C12' 1.379(4) . ? C12' C13' 1.363(4) . ? C13' C14' 1.378(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 C1 N1 N2 110.3(2) . . ? C1 N1 C9 129.7(2) . . ? N2 N1 C9 120.0(2) . . ? N3 N2 N1 106.9(2) . . ? N2 N3 C2 109.6(2) . . ? O1 N4 O2 123.7(3) . . ? O1 N4 C13 118.5(2) . . ? O2 N4 C13 117.7(3) . . ? N1 C1 C2 105.9(2) . . ? C1 C2 N3 107.3(2) . . ? C1 C2 C3 130.1(3) . . ? N3 C2 C3 122.6(2) . . ? C8 C3 C4 119.0(3) . . ? C8 C3 C2 120.7(2) . . ? C4 C3 C2 120.2(3) . . ? C5 C4 C3 119.9(3) . . ? C6 C5 C4 121.2(3) . . ? C7 C6 C5 118.6(3) . . ? C6 C7 C8 121.5(3) . . ? C6 C7 Br1 120.4(2) . . ? C8 C7 Br1 118.1(2) . . ? C3 C8 C7 119.7(3) . . ? C10 C9 C14 120.8(3) . . ? C10 C9 N1 119.4(2) . . ? C14 C9 N1 119.9(2) . . ? C9 C10 C11 120.2(3) . . ? C12 C11 C10 120.2(3) . . ? C13 C12 C11 118.0(3) . . ? C12 C13 C14 123.6(3) . . ? C12 C13 N4 118.5(2) . . ? C14 C13 N4 117.9(3) . . ? C13 C14 C9 117.1(3) . . ? C1' N1' N2' 110.1(2) . . ? C1' N1' C9' 130.2(2) . . ? N2' N1' C9' 119.7(2) . . ? N3' N2' N1' 106.9(2) . . ? N2' N3' C2' 109.7(2) . . ? O1' N4' O2' 124.0(3) . . ? O1' N4' C13' 118.4(2) . . ? O2' N4' C13' 117.6(3) . . ? N1' C1' C2' 106.0(2) . . ? C1' C2' N3' 107.4(2) . . ? C1' C2' C3' 130.5(2) . . ? N3' C2' C3' 122.1(2) . . ? C8' C3' C4' 119.0(3) . . ? C8' C3' C2' 120.5(2) . . ? C4' C3' C2' 120.5(3) . . ? C5' C4' C3' 120.3(3) . . ? C4' C5' C6' 121.2(3) . . ? C7' C6' C5' 118.0(3) . . ? C6' C7' C8' 121.9(3) . . ? C6' C7' Br1' 119.8(2) . . ? C8' C7' Br1' 118.2(2) . . ? C7' C8' C3' 119.6(3) . . ? C14' C9' C10' 120.9(3) . . ? C14' C9' N1' 120.4(2) . . ? C10' C9' N1' 118.7(2) . . ? C11' C10' C9' 120.1(3) . . ? C10' C11' C12' 119.8(3) . . ? C13' C12' C11' 118.7(3) . . ? C12' C13' C14' 123.4(3) . . ? C12' C13' N4' 118.7(3) . . ? C14' C13' N4' 117.9(3) . . ? C13' C14' C9' 117.1(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 C1 N1 N2 N3 0.2(3) . . . . ? C9 N1 N2 N3 -178.5(2) . . . . ? N1 N2 N3 C2 -0.1(3) . . . . ? N2 N1 C1 C2 -0.2(3) . . . . ? C9 N1 C1 C2 178.3(3) . . . . ? N1 C1 C2 N3 0.1(3) . . . . ? N1 C1 C2 C3 -178.9(3) . . . . ? N2 N3 C2 C1 0.0(3) . . . . ? N2 N3 C2 C3 179.1(3) . . . . ? C1 C2 C3 C8 -170.5(3) . . . . ? N3 C2 C3 C8 10.7(4) . . . . ? C1 C2 C3 C4 11.7(5) . . . . ? N3 C2 C3 C4 -167.2(3) . . . . ? C8 C3 C4 C5 -0.2(4) . . . . ? C2 C3 C4 C5 177.8(3) . . . . ? C3 C4 C5 C6 -0.7(5) . . . . ? C4 C5 C6 C7 0.9(5) . . . . ? C5 C6 C7 C8 -0.3(5) . . . . ? C5 C6 C7 Br1 -179.2(2) . . . . ? C4 C3 C8 C7 0.8(4) . . . . ? C2 C3 C8 C7 -177.1(3) . . . . ? C6 C7 C8 C3 -0.6(4) . . . . ? Br1 C7 C8 C3 178.4(2) . . . . ? C1 N1 C9 C10 170.6(3) . . . . ? N2 N1 C9 C10 -11.0(4) . . . . ? C1 N1 C9 C14 -9.1(4) . . . . ? N2 N1 C9 C14 169.2(3) . . . . ? C14 C9 C10 C11 -1.5(4) . . . . ? N1 C9 C10 C11 178.7(3) . . . . ? C9 C10 C11 C12 1.3(5) . . . . ? C10 C11 C12 C13 -0.2(4) . . . . ? C11 C12 C13 C14 -0.7(4) . . . . ? C11 C12 C13 N4 179.3(3) . . . . ? O1 N4 C13 C12 -176.5(3) . . . . ? O2 N4 C13 C12 3.0(4) . . . . ? O1 N4 C13 C14 3.5(4) . . . . ? O2 N4 C13 C14 -177.0(3) . . . . ? C12 C13 C14 C9 0.5(4) . . . . ? N4 C13 C14 C9 -179.5(2) . . . . ? C10 C9 C14 C13 0.7(4) . . . . ? N1 C9 C14 C13 -179.6(2) . . . . ? C1' N1' N2' N3' -0.3(3) . . . . ? C9' N1' N2' N3' -178.8(2) . . . . ? N1' N2' N3' C2' 0.5(3) . . . . ? N2' N1' C1' C2' 0.0(3) . . . . ? C9' N1' C1' C2' 178.3(2) . . . . ? N1' C1' C2' N3' 0.3(3) . . . . ? N1' C1' C2' C3' -178.2(3) . . . . ? N2' N3' C2' C1' -0.5(3) . . . . ? N2' N3' C2' C3' 178.1(3) . . . . ? C1' C2' C3' C8' 179.2(3) . . . . ? N3' C2' C3' C8' 1.0(4) . . . . ? C1' C2' C3' C4' 0.3(5) . . . . ? N3' C2' C3' C4' -177.9(3) . . . . ? C8' C3' C4' C5' 0.0(4) . . . . ? C2' C3' C4' C5' 178.9(3) . . . . ? C3' C4' C5' C6' 0.8(5) . . . . ? C4' C5' C6' C7' -0.9(5) . . . . ? C5' C6' C7' C8' 0.3(4) . . . . ? C5' C6' C7' Br1' 179.8(2) . . . . ? C6' C7' C8' C3' 0.5(4) . . . . ? Br1' C7' C8' C3' -179.0(2) . . . . ? C4' C3' C8' C7' -0.6(4) . . . . ? C2' C3' C8' C7' -179.5(2) . . . . ? C1' N1' C9' C14' -3.7(4) . . . . ? N2' N1' C9' C14' 174.5(3) . . . . ? C1' N1' C9' C10' 176.3(3) . . . . ? N2' N1' C9' C10' -5.6(4) . . . . ? C14' C9' C10' C11' 0.5(5) . . . . ? N1' C9' C10' C11' -179.4(3) . . . . ? C9' C10' C11' C12' -0.1(5) . . . . ? C10' C11' C12' C13' -0.6(5) . . . . ? C11' C12' C13' C14' 0.9(5) . . . . ? C11' C12' C13' N4' -179.5(3) . . . . ? O1' N4' C13' C12' -176.6(3) . . . . ? O2' N4' C13' C12' 3.6(4) . . . . ? O1' N4' C13' C14' 3.0(4) . . . . ? O2' N4' C13' C14' -176.8(3) . . . . ? C12' C13' C14' C9' -0.6(4) . . . . ? N4' C13' C14' C9' 179.8(2) . . . . ? C10' C9' C14' C13' -0.2(4) . . . . ? N1' C9' C14' C13' 179.8(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 C8' H8' Br1 0.93 2.98 3.908(3) 172.1 1_454 C8 H8 Br1' 0.93 3.04 3.926(3) 160.8 1_656 C14' H14' O1 0.93 2.66 3.584(4) 173.4 1_565 C4' H4' O2 0.93 2.55 3.391(4) 150.9 1_565 C1' H1' O1 0.93 2.44 3.351(4) 167.1 1_565 C4 H4 O2' 0.93 2.67 3.478(4) 145.8 1_545 C1 H1 O1' 0.93 2.47 3.395(3) 172.8 1_545 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.436 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.058 #===END data_15 _database_code_depnum_ccdc_archive 'CCDC 679563' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 Br N4 O2' _chemical_formula_sum 'C14 H9 Br N4 O2' _chemical_formula_weight 345.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M 'P 21/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 8.667(3) _cell_length_b 5.2323(18) _cell_length_c 30.304(11) _cell_angle_alpha 90.00 _cell_angle_beta 96.248(6) _cell_angle_gamma 90.00 _cell_volume 1366.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1536 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 22.18 _exptl_crystal_description PLATE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.678 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 3.019 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.4013 _exptl_absorpt_correction_T_max 0.9149 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6524 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2403 _reflns_number_gt 1718 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _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 SHELXTL _computing_publication_material 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^)+(0.0536P)^2^+0.8225P] 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 REFALL _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2403 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0675 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1186 _refine_ls_wR_factor_gt 0.1064 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 0.41429(6) 0.60503(13) 0.198319(15) 0.1014(3) Uani 1 1 d . . . O1 O 0.5458(3) -0.0305(5) 0.55246(9) 0.0634(7) Uani 1 1 d . . . O2 O 0.6556(3) 0.0169(6) 0.61895(9) 0.0702(8) Uani 1 1 d . . . N1 N 0.7654(3) 0.6420(5) 0.46216(9) 0.0449(7) Uani 1 1 d . . . N2 N 0.8255(4) 0.8674(5) 0.45012(11) 0.0584(8) Uani 1 1 d . . . N3 N 0.7884(4) 0.8931(6) 0.40738(10) 0.0590(8) Uani 1 1 d . . . N4 N 0.6364(3) 0.0780(5) 0.58010(10) 0.0507(7) Uani 1 1 d . . . C1 C 0.6902(4) 0.5279(7) 0.42642(11) 0.0453(8) Uani 1 1 d . . . C2 C 0.7042(4) 0.6861(6) 0.39176(12) 0.0471(8) Uani 1 1 d . . . C3 C 0.6396(4) 0.6623(6) 0.34477(11) 0.0477(8) Uani 1 1 d . . . C4 C 0.5360(6) 0.4728(9) 0.33145(14) 0.0710(13) Uani 1 1 d . . . C5 C 0.4709(6) 0.4555(11) 0.28808(15) 0.0783(13) Uani 1 1 d . . . C6 C 0.5083(5) 0.6278(9) 0.25769(13) 0.0637(11) Uani 1 1 d . . . C7 C 0.6127(6) 0.8163(10) 0.26996(16) 0.0788(14) Uani 1 1 d . . . C8 C 0.6777(6) 0.8330(9) 0.31329(15) 0.0706(12) Uani 1 1 d . . . C9 C 0.7879(4) 0.5634(6) 0.50744(11) 0.0438(8) Uani 1 1 d . . . C10 C 0.8956(4) 0.6891(7) 0.53709(12) 0.0491(9) Uani 1 1 d . . . C11 C 0.9149(4) 0.6146(7) 0.58101(13) 0.0543(10) Uani 1 1 d . . . C12 C 0.8314(4) 0.4153(7) 0.59597(13) 0.0513(9) Uani 1 1 d . . . C13 C 0.7270(4) 0.2922(6) 0.56537(11) 0.0430(8) Uani 1 1 d . . . C14 C 0.7023(4) 0.3623(6) 0.52129(11) 0.0416(8) Uani 1 1 d . . . H1 H 0.644(4) 0.376(6) 0.4279(10) 0.041(9) Uiso 1 1 d . . . H4 H 0.514(5) 0.367(7) 0.3514(14) 0.068(13) Uiso 1 1 d . . . H5 H 0.408(7) 0.319(11) 0.2822(19) 0.13(2) Uiso 1 1 d . . . H7 H 0.638(5) 0.927(9) 0.2500(16) 0.089(16) Uiso 1 1 d . . . H8 H 0.740(4) 0.955(7) 0.3218(12) 0.055(11) Uiso 1 1 d . . . H10 H 0.948(4) 0.830(7) 0.5272(11) 0.049(10) Uiso 1 1 d . . . H11 H 0.986(4) 0.699(7) 0.5991(12) 0.055(10) Uiso 1 1 d . . . H12 H 0.844(4) 0.361(6) 0.6247(13) 0.055(10) Uiso 1 1 d . . . H14 H 0.633(4) 0.276(6) 0.5017(11) 0.049(9) Uiso 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 0.0942(4) 0.1524(6) 0.0535(3) -0.0074(3) -0.0107(2) 0.0228(3) O1 0.0676(17) 0.0635(16) 0.0569(16) -0.0029(14) -0.0037(13) -0.0266(14) O2 0.0805(19) 0.0779(19) 0.0502(17) 0.0164(15) -0.0014(14) -0.0155(16) N1 0.0476(16) 0.0382(15) 0.0483(17) -0.0022(13) 0.0023(13) -0.0084(13) N2 0.068(2) 0.0460(18) 0.060(2) -0.0022(15) 0.0003(16) -0.0216(15) N3 0.071(2) 0.0497(18) 0.0549(19) 0.0016(15) 0.0007(16) -0.0184(15) N4 0.0515(18) 0.0491(18) 0.0513(19) -0.0011(15) 0.0051(14) -0.0013(14) C1 0.050(2) 0.0366(19) 0.048(2) -0.0045(17) -0.0009(16) -0.0104(17) C2 0.049(2) 0.0381(18) 0.054(2) 0.0009(17) 0.0079(16) -0.0028(16) C3 0.050(2) 0.046(2) 0.047(2) 0.0018(17) 0.0042(15) -0.0035(17) C4 0.092(3) 0.070(3) 0.050(2) 0.006(2) 0.006(2) -0.031(3) C5 0.083(3) 0.093(4) 0.058(3) -0.004(3) 0.001(2) -0.026(3) C6 0.061(2) 0.082(3) 0.048(2) -0.002(2) 0.0031(18) 0.010(2) C7 0.100(4) 0.080(3) 0.055(3) 0.017(3) 0.007(2) -0.008(3) C8 0.081(3) 0.063(3) 0.066(3) 0.006(2) 0.001(2) -0.023(2) C9 0.0403(18) 0.0419(19) 0.049(2) -0.0073(16) 0.0034(15) 0.0002(15) C10 0.045(2) 0.045(2) 0.057(2) -0.0074(18) 0.0036(17) -0.0082(17) C11 0.051(2) 0.055(2) 0.054(2) -0.0149(19) -0.0065(18) -0.0097(19) C12 0.053(2) 0.057(2) 0.043(2) -0.0022(18) -0.0013(16) -0.0037(18) C13 0.0411(18) 0.0392(18) 0.048(2) -0.0043(16) 0.0032(14) -0.0022(15) C14 0.0386(17) 0.0414(19) 0.0435(19) -0.0075(16) -0.0019(15) -0.0041(15) _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 C6 1.896(4) . ? O1 N4 1.224(4) . ? O2 N4 1.214(4) . ? N1 C1 1.342(4) . ? N1 N2 1.356(4) . ? N1 C9 1.425(4) . ? N2 N3 1.307(4) . ? N3 C2 1.362(4) . ? N4 C13 1.465(4) . ? C1 C2 1.353(5) . ? C2 C3 1.478(5) . ? C3 C4 1.369(5) . ? C3 C8 1.373(5) . ? C4 C5 1.376(6) . ? C5 C6 1.353(6) . ? C6 C7 1.363(6) . ? C7 C8 1.374(6) . ? C9 C14 1.379(5) . ? C9 C10 1.389(5) . ? C10 C11 1.380(5) . ? C11 C12 1.374(5) . ? C12 C13 1.382(5) . ? C13 C14 1.379(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 N1 N2 109.7(3) . . ? C1 N1 C9 130.7(3) . . ? N2 N1 C9 119.6(3) . . ? N3 N2 N1 107.2(3) . . ? N2 N3 C2 109.1(3) . . ? O2 N4 O1 123.5(3) . . ? O2 N4 C13 118.4(3) . . ? O1 N4 C13 118.1(3) . . ? N1 C1 C2 106.1(3) . . ? C1 C2 N3 107.9(3) . . ? C1 C2 C3 129.8(3) . . ? N3 C2 C3 122.3(3) . . ? C4 C3 C8 117.8(4) . . ? C4 C3 C2 120.8(3) . . ? C8 C3 C2 121.4(3) . . ? C3 C4 C5 121.1(4) . . ? C6 C5 C4 120.2(4) . . ? C5 C6 C7 119.9(4) . . ? C5 C6 Br1 119.6(3) . . ? C7 C6 Br1 120.5(3) . . ? C6 C7 C8 119.9(4) . . ? C3 C8 C7 121.2(4) . . ? C14 C9 C10 120.7(3) . . ? C14 C9 N1 119.4(3) . . ? C10 C9 N1 119.9(3) . . ? C11 C10 C9 119.5(4) . . ? C12 C11 C10 121.3(4) . . ? C11 C12 C13 117.5(4) . . ? C14 C13 C12 123.1(3) . . ? C14 C13 N4 117.8(3) . . ? C12 C13 N4 119.0(3) . . ? C9 C14 C13 117.8(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 C1 N1 N2 N3 -0.1(4) . . . . ? C9 N1 N2 N3 -179.9(3) . . . . ? N1 N2 N3 C2 0.2(4) . . . . ? N2 N1 C1 C2 0.0(4) . . . . ? C9 N1 C1 C2 179.7(3) . . . . ? N1 C1 C2 N3 0.2(4) . . . . ? N1 C1 C2 C3 -177.5(3) . . . . ? N2 N3 C2 C1 -0.2(4) . . . . ? N2 N3 C2 C3 177.6(3) . . . . ? C1 C2 C3 C4 7.6(6) . . . . ? N3 C2 C3 C4 -169.8(4) . . . . ? C1 C2 C3 C8 -174.3(4) . . . . ? N3 C2 C3 C8 8.3(6) . . . . ? C8 C3 C4 C5 -0.7(7) . . . . ? C2 C3 C4 C5 177.5(4) . . . . ? C3 C4 C5 C6 -0.2(8) . . . . ? C4 C5 C6 C7 1.1(7) . . . . ? C4 C5 C6 Br1 -178.8(4) . . . . ? C5 C6 C7 C8 -1.0(7) . . . . ? Br1 C6 C7 C8 178.8(4) . . . . ? C4 C3 C8 C7 0.8(7) . . . . ? C2 C3 C8 C7 -177.4(4) . . . . ? C6 C7 C8 C3 0.1(7) . . . . ? C1 N1 C9 C14 -12.5(5) . . . . ? N2 N1 C9 C14 167.2(3) . . . . ? C1 N1 C9 C10 167.3(3) . . . . ? N2 N1 C9 C10 -12.9(5) . . . . ? C14 C9 C10 C11 -1.2(5) . . . . ? N1 C9 C10 C11 179.0(3) . . . . ? C9 C10 C11 C12 1.1(6) . . . . ? C10 C11 C12 C13 -0.1(5) . . . . ? C11 C12 C13 C14 -0.8(5) . . . . ? C11 C12 C13 N4 179.7(3) . . . . ? O2 N4 C13 C14 -179.0(3) . . . . ? O1 N4 C13 C14 1.3(4) . . . . ? O2 N4 C13 C12 0.5(5) . . . . ? O1 N4 C13 C12 -179.2(3) . . . . ? C10 C9 C14 C13 0.3(5) . . . . ? N1 C9 C14 C13 -179.8(3) . . . . ? C12 C13 C14 C9 0.7(5) . . . . ? N4 C13 C14 C9 -179.8(3) . . . . ? 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 C10 H10 N2 0.93(4) 2.56(4) 3.342(5) 142(3) 3_776 C4 H4 O2 0.86(4) 2.70(4) 3.482(5) 153(3) 3_656 C14 H14 O1 0.92(3) 2.49(3) 3.404(4) 177(3) 3_656 C1 H1 O1 0.89(3) 2.56(3) 3.413(5) 161(3) 3_656 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.645 _refine_diff_density_min -0.540 _refine_diff_density_rms 0.057 #===END data_16 _database_code_depnum_ccdc_archive 'CCDC 679564' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 N4 O2' _chemical_formula_sum 'C14 H10 N4 O2' _chemical_formula_weight 266.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.757(2) _cell_length_b 7.198(3) _cell_length_c 14.862(6) _cell_angle_alpha 101.081(6) _cell_angle_beta 99.217(6) _cell_angle_gamma 90.859(6) _cell_volume 595.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 2295 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 27.74 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.69 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9315 _exptl_absorpt_correction_T_max 0.9917 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4652 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_sigmaI/netI 0.0227 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2296 _reflns_number_gt 2006 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0543P)^2^+0.1231P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2296 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0414 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.1042 _refine_ls_wR_factor_gt 0.0996 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0476(2) -0.2112(2) 0.00540(8) 0.0689(4) Uani 1 1 d . . . O2 O -0.2953(2) -0.1897(2) 0.04544(8) 0.0776(4) Uani 1 1 d . . . N1 N 0.32113(18) 0.18190(15) 0.42594(7) 0.0320(3) Uani 1 1 d . . . N2 N 0.55834(19) 0.19502(17) 0.45150(8) 0.0393(3) Uani 1 1 d . . . N3 N 0.60249(19) 0.27687(17) 0.53911(8) 0.0391(3) Uani 1 1 d . . . N4 N -0.0818(2) -0.16618(18) 0.06263(8) 0.0465(3) Uani 1 1 d . . . C1 C 0.2148(2) 0.25638(18) 0.49866(9) 0.0329(3) Uani 1 1 d . . . C2 C 0.3947(2) 0.31752(17) 0.57052(9) 0.0312(3) Uani 1 1 d . . . C3 C 0.3868(2) 0.40877(17) 0.66732(8) 0.0312(3) Uani 1 1 d . . . C4 C 0.5798(2) 0.40535(19) 0.73656(9) 0.0358(3) Uani 1 1 d . . . C5 C 0.5715(3) 0.4882(2) 0.82794(10) 0.0413(3) Uani 1 1 d . . . C6 C 0.3714(3) 0.5752(2) 0.85153(10) 0.0421(3) Uani 1 1 d . . . C7 C 0.1791(2) 0.5797(2) 0.78347(10) 0.0403(3) Uani 1 1 d . . . C8 C 0.1858(2) 0.49702(19) 0.69168(10) 0.0361(3) Uani 1 1 d . . . C9 C 0.2188(2) 0.09372(17) 0.33377(8) 0.0308(3) Uani 1 1 d . . . C10 C -0.0036(2) 0.00526(19) 0.31776(9) 0.0352(3) Uani 1 1 d . . . C11 C -0.1025(2) -0.07915(19) 0.22806(9) 0.0361(3) Uani 1 1 d . . . C12 C 0.0256(2) -0.07538(18) 0.15746(9) 0.0348(3) Uani 1 1 d . . . C13 C 0.2481(2) 0.01044(19) 0.17242(9) 0.0373(3) Uani 1 1 d . . . C14 C 0.3444(2) 0.09852(19) 0.26166(9) 0.0348(3) Uani 1 1 d . . . H1 H 0.050(3) 0.2583(19) 0.4931(10) 0.038(4) Uiso 1 1 d . . . H4 H 0.722(3) 0.344(2) 0.7209(10) 0.038(4) Uiso 1 1 d . . . H5 H 0.708(3) 0.486(2) 0.8741(12) 0.049(4) Uiso 1 1 d . . . H6 H 0.361(3) 0.631(2) 0.9145(12) 0.052(4) Uiso 1 1 d . . . H7 H 0.036(3) 0.643(2) 0.7998(11) 0.046(4) Uiso 1 1 d . . . H8 H 0.049(3) 0.499(2) 0.6445(11) 0.039(4) Uiso 1 1 d . . . H10 H -0.090(3) 0.001(2) 0.3681(11) 0.046(4) Uiso 1 1 d . . . H11 H -0.257(3) -0.141(2) 0.2156(11) 0.045(4) Uiso 1 1 d . . . H13 H 0.334(3) 0.012(2) 0.1211(11) 0.048(4) Uiso 1 1 d . . . H14 H 0.498(3) 0.163(2) 0.2743(11) 0.043(4) Uiso 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 O1 0.0747(8) 0.0883(9) 0.0353(6) -0.0129(6) 0.0136(6) 0.0074(7) O2 0.0543(8) 0.1229(12) 0.0427(7) -0.0025(7) -0.0047(6) -0.0254(7) N1 0.0307(5) 0.0361(6) 0.0274(5) 0.0019(4) 0.0051(4) 0.0000(4) N2 0.0317(6) 0.0509(7) 0.0328(6) 0.0017(5) 0.0058(5) -0.0004(5) N3 0.0347(6) 0.0490(7) 0.0308(6) 0.0013(5) 0.0052(5) -0.0009(5) N4 0.0543(8) 0.0501(7) 0.0308(6) 0.0012(5) 0.0026(6) -0.0037(6) C1 0.0303(7) 0.0363(7) 0.0307(7) 0.0019(5) 0.0067(5) 0.0008(5) C2 0.0323(6) 0.0307(6) 0.0305(7) 0.0051(5) 0.0059(5) -0.0004(5) C3 0.0333(6) 0.0297(6) 0.0293(7) 0.0030(5) 0.0051(5) -0.0040(5) C4 0.0326(7) 0.0382(7) 0.0344(7) 0.0027(5) 0.0045(5) 0.0005(5) C5 0.0396(7) 0.0476(8) 0.0320(7) 0.0025(6) -0.0011(6) -0.0035(6) C6 0.0474(8) 0.0442(8) 0.0307(7) -0.0042(6) 0.0096(6) -0.0059(6) C7 0.0379(7) 0.0387(7) 0.0421(8) -0.0016(6) 0.0114(6) 0.0005(6) C8 0.0335(7) 0.0372(7) 0.0353(7) 0.0038(5) 0.0031(6) 0.0006(5) C9 0.0333(6) 0.0298(6) 0.0279(6) 0.0027(5) 0.0048(5) 0.0021(5) C10 0.0357(7) 0.0396(7) 0.0307(7) 0.0047(5) 0.0098(5) -0.0013(5) C11 0.0338(7) 0.0371(7) 0.0355(7) 0.0037(6) 0.0045(5) -0.0033(5) C12 0.0400(7) 0.0346(6) 0.0277(7) 0.0021(5) 0.0040(5) 0.0024(5) C13 0.0398(7) 0.0428(7) 0.0302(7) 0.0051(6) 0.0112(6) 0.0020(6) C14 0.0332(7) 0.0380(7) 0.0329(7) 0.0040(5) 0.0080(5) -0.0022(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 O1 N4 1.2195(17) . ? O2 N4 1.2172(18) . ? N1 C1 1.3524(16) . ? N1 N2 1.3542(16) . ? N1 C9 1.4221(16) . ? N2 N3 1.3045(16) . ? N3 C2 1.3680(17) . ? N4 C12 1.4663(18) . ? C1 C2 1.3631(18) . ? C2 C3 1.4704(18) . ? C3 C4 1.3925(19) . ? C3 C8 1.3931(18) . ? C4 C5 1.383(2) . ? C5 C6 1.382(2) . ? C6 C7 1.380(2) . ? C7 C8 1.386(2) . ? C9 C10 1.3862(18) . ? C9 C14 1.3905(18) . ? C10 C11 1.3804(19) . ? C11 C12 1.3795(19) . ? C12 C13 1.380(2) . ? C13 C14 1.3781(19) . ? 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 N1 N2 110.54(10) . . ? C1 N1 C9 129.40(11) . . ? N2 N1 C9 120.03(10) . . ? N3 N2 N1 107.05(10) . . ? N2 N3 C2 109.30(11) . . ? O2 N4 O1 123.90(13) . . ? O2 N4 C12 117.94(12) . . ? O1 N4 C12 118.15(13) . . ? N1 C1 C2 104.96(11) . . ? C1 C2 N3 108.14(11) . . ? C1 C2 C3 129.73(12) . . ? N3 C2 C3 122.12(11) . . ? C4 C3 C8 118.91(12) . . ? C4 C3 C2 120.23(12) . . ? C8 C3 C2 120.86(12) . . ? C5 C4 C3 120.39(13) . . ? C6 C5 C4 120.34(13) . . ? C7 C6 C5 119.78(13) . . ? C6 C7 C8 120.29(13) . . ? C7 C8 C3 120.30(13) . . ? C10 C9 C14 121.49(12) . . ? C10 C9 N1 119.35(11) . . ? C14 C9 N1 119.16(11) . . ? C11 C10 C9 119.06(12) . . ? C12 C11 C10 118.75(13) . . ? C11 C12 C13 122.86(12) . . ? C11 C12 N4 118.04(12) . . ? C13 C12 N4 119.11(12) . . ? C14 C13 C12 118.35(12) . . ? C13 C14 C9 119.46(12) . . ? 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 C1 N1 N2 N3 -0.10(14) . . . . ? C9 N1 N2 N3 -178.47(10) . . . . ? N1 N2 N3 C2 -0.18(14) . . . . ? N2 N1 C1 C2 0.33(14) . . . . ? C9 N1 C1 C2 178.50(12) . . . . ? N1 C1 C2 N3 -0.43(14) . . . . ? N1 C1 C2 C3 -179.28(12) . . . . ? N2 N3 C2 C1 0.39(15) . . . . ? N2 N3 C2 C3 179.34(11) . . . . ? C1 C2 C3 C4 159.14(13) . . . . ? N3 C2 C3 C4 -19.57(18) . . . . ? C1 C2 C3 C8 -19.8(2) . . . . ? N3 C2 C3 C8 161.51(12) . . . . ? C8 C3 C4 C5 0.0(2) . . . . ? C2 C3 C4 C5 -178.90(12) . . . . ? C3 C4 C5 C6 0.0(2) . . . . ? C4 C5 C6 C7 -0.1(2) . . . . ? C5 C6 C7 C8 0.1(2) . . . . ? C6 C7 C8 C3 0.0(2) . . . . ? C4 C3 C8 C7 0.0(2) . . . . ? C2 C3 C8 C7 178.89(12) . . . . ? C1 N1 C9 C10 -26.69(19) . . . . ? N2 N1 C9 C10 151.33(12) . . . . ? C1 N1 C9 C14 153.21(13) . . . . ? N2 N1 C9 C14 -28.76(17) . . . . ? C14 C9 C10 C11 -0.3(2) . . . . ? N1 C9 C10 C11 179.64(11) . . . . ? C9 C10 C11 C12 1.1(2) . . . . ? C10 C11 C12 C13 -0.5(2) . . . . ? C10 C11 C12 N4 179.83(12) . . . . ? O2 N4 C12 C11 21.4(2) . . . . ? O1 N4 C12 C11 -159.63(14) . . . . ? O2 N4 C12 C13 -158.33(15) . . . . ? O1 N4 C12 C13 20.7(2) . . . . ? C11 C12 C13 C14 -1.0(2) . . . . ? N4 C12 C13 C14 178.67(12) . . . . ? C12 C13 C14 C9 1.8(2) . . . . ? C10 C9 C14 C13 -1.2(2) . . . . ? N1 C9 C14 C13 178.85(11) . . . . ? 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 C6 H6 O1 0.956(17) 2.575(17) 3.342(2) 137.3(13) 1_566 C6 H6 O2 0.956(17) 2.660(17) 3.333(2) 127.7(12) 1_666 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.195 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.035 #===END data_17 _database_code_depnum_ccdc_archive 'CCDC 679565' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 Br N4 O2' _chemical_formula_sum 'C14 H9 Br N4 O2' _chemical_formula_weight 345.16 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.52(2) _cell_length_b 7.057(5) _cell_length_c 13.022(9) _cell_angle_alpha 90.00 _cell_angle_beta 97.405(12) _cell_angle_gamma 90.00 _cell_volume 2690(3) _cell_formula_units_Z 8 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1795 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 23.17 _exptl_crystal_description needle _exptl_crystal_colour ? _exptl_crystal_size_max 0.68 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas red _exptl_crystal_density_diffrn 1.705 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 3.066 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2296 _exptl_absorpt_correction_T_max 0.5791 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6468 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0458 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2377 _reflns_number_gt 1764 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0577P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2377 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0556 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.1037 _refine_ls_wR_factor_gt 0.0953 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 0.43035(6) 0.18927(18) 0.27418(14) 0.0710(3) Uani 0.80 1 d P A 1 Br1' Br 0.4353(3) 0.2702(9) 0.2774(6) 0.103(2) Uani 0.20 1 d P A 2 O1 O 0.09916(9) 0.3109(4) 0.0456(2) 0.0885(8) Uani 1 1 d . . . O2 O 0.14396(9) 0.3681(4) -0.06779(19) 0.0954(8) Uani 1 1 d . . . N1 N 0.28795(7) 0.3591(3) 0.33043(15) 0.0413(5) Uani 1 1 d . . . N2 N 0.28230(8) 0.3975(4) 0.42944(16) 0.0541(6) Uani 1 1 d . . . N3 N 0.32249(8) 0.3865(4) 0.48381(16) 0.0577(6) Uani 1 1 d . . . N4 N 0.13677(9) 0.3428(4) 0.0213(2) 0.0625(7) Uani 1 1 d . . . C1 C 0.33215(9) 0.3245(4) 0.32299(19) 0.0451(7) Uani 1 1 d . . . H1 H 0.3448 0.2952 0.2631 0.054 Uiso 1 1 calc R . . C2 C 0.35481(9) 0.3409(4) 0.42078(19) 0.0442(6) Uani 1 1 d . . . C3 C 0.40237(10) 0.3166(4) 0.4678(2) 0.0495(7) Uani 1 1 d . A . C4 C 0.41215(12) 0.3527(5) 0.5733(2) 0.0776(11) Uani 1 1 d . . . H4 H 0.3889 0.3934 0.6099 0.093 Uiso 1 1 calc R . . C5 C 0.45566(15) 0.3295(6) 0.6251(3) 0.0989(14) Uani 1 1 d . . . H5 H 0.4613 0.3552 0.6956 0.119 Uiso 1 1 calc R . . C6 C 0.49054(13) 0.2691(6) 0.5733(3) 0.0886(12) Uani 1 1 d . . . H6 H 0.5196 0.2504 0.6089 0.106 Uiso 1 1 calc R . . C7 C 0.48234(12) 0.2365(5) 0.4692(3) 0.0727(10) Uani 1 1 d . A . H7 H 0.5061 0.1997 0.4330 0.087 Uiso 1 1 calc R . . C8 C 0.43861(11) 0.2584(4) 0.4175(2) 0.0556(7) Uani 1 1 d . . . C9 C 0.24925(8) 0.3599(4) 0.25256(18) 0.0387(6) Uani 1 1 d . . . C10 C 0.25549(9) 0.3902(4) 0.15035(18) 0.0455(6) Uani 1 1 d . . . H10 H 0.2845 0.4127 0.1326 0.055 Uiso 1 1 calc R . . C11 C 0.21827(9) 0.3867(4) 0.07559(19) 0.0477(7) Uani 1 1 d . . . H11 H 0.2218 0.4076 0.0066 0.057 Uiso 1 1 calc R . . C12 C 0.17576(9) 0.3522(4) 0.1033(2) 0.0471(7) Uani 1 1 d . . . C13 C 0.16879(9) 0.3252(4) 0.2052(2) 0.0502(7) Uani 1 1 d . . . H13 H 0.1396 0.3051 0.2226 0.060 Uiso 1 1 calc R . . C14 C 0.20610(9) 0.3286(4) 0.2802(2) 0.0469(7) Uani 1 1 d . . . H14 H 0.2024 0.3101 0.3494 0.056 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 0.0519(5) 0.1101(8) 0.0532(3) -0.0097(5) 0.0148(3) 0.0054(5) Br1' 0.0545(18) 0.201(7) 0.0552(15) -0.012(4) 0.0148(11) -0.004(4) O1 0.0478(15) 0.123(2) 0.0924(19) -0.0035(15) -0.0009(13) -0.0046(14) O2 0.0789(18) 0.147(2) 0.0548(14) 0.0024(15) -0.0117(13) -0.0035(17) N1 0.0425(13) 0.0469(14) 0.0361(11) -0.0010(9) 0.0113(9) -0.0005(10) N2 0.0535(15) 0.0724(17) 0.0384(12) -0.0064(11) 0.0137(11) 0.0036(13) N3 0.0518(16) 0.0792(18) 0.0422(13) -0.0059(12) 0.0065(11) 0.0052(13) N4 0.0530(18) 0.0662(18) 0.0658(18) -0.0051(13) -0.0017(13) 0.0054(13) C1 0.0431(16) 0.0526(18) 0.0416(14) -0.0023(12) 0.0129(12) 0.0038(13) C2 0.0487(16) 0.0443(16) 0.0405(14) 0.0016(11) 0.0096(12) 0.0009(12) C3 0.0511(17) 0.0515(18) 0.0452(15) 0.0023(13) 0.0031(13) 0.0027(14) C4 0.062(2) 0.115(3) 0.0520(18) -0.0137(18) -0.0046(15) 0.020(2) C5 0.079(3) 0.150(4) 0.061(2) -0.019(2) -0.016(2) 0.019(3) C6 0.055(2) 0.125(3) 0.080(3) -0.009(2) -0.0141(19) 0.018(2) C7 0.051(2) 0.090(3) 0.076(2) -0.0021(19) 0.0019(17) 0.0081(18) C8 0.0498(18) 0.0627(19) 0.0543(17) 0.0033(14) 0.0064(13) 0.0008(14) C9 0.0403(15) 0.0365(14) 0.0402(13) 0.0001(10) 0.0090(11) -0.0001(11) C10 0.0450(15) 0.0508(16) 0.0422(14) 0.0002(12) 0.0119(12) -0.0045(13) C11 0.0515(17) 0.0532(17) 0.0392(14) -0.0011(12) 0.0093(12) 0.0010(13) C12 0.0442(16) 0.0465(17) 0.0495(15) -0.0036(12) 0.0021(12) 0.0029(13) C13 0.0401(15) 0.0554(19) 0.0578(17) 0.0028(13) 0.0162(13) 0.0017(13) C14 0.0474(16) 0.0525(18) 0.0428(14) 0.0059(12) 0.0139(12) 0.0029(13) _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 1.914(4) . ? Br1' C8 1.817(8) . ? O1 N4 1.214(4) . ? O2 N4 1.219(3) . ? N1 C1 1.343(3) . ? N1 N2 1.349(3) . ? N1 C9 1.426(3) . ? N2 N3 1.303(3) . ? N3 C2 1.374(3) . ? N4 C12 1.467(4) . ? C1 C2 1.365(4) . ? C2 C3 1.467(4) . ? C3 C8 1.387(4) . ? C3 C4 1.391(4) . ? C4 C5 1.381(5) . ? C5 C6 1.369(6) . ? C6 C7 1.366(5) . ? C7 C8 1.385(5) . ? C9 C10 1.384(3) . ? C9 C14 1.385(4) . ? C10 C11 1.371(4) . ? C11 C12 1.371(4) . ? C12 C13 1.382(4) . ? C13 C14 1.375(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 C1 N1 N2 110.3(2) . . ? C1 N1 C9 130.2(2) . . ? N2 N1 C9 119.5(2) . . ? N3 N2 N1 106.9(2) . . ? N2 N3 C2 110.0(2) . . ? O1 N4 O2 123.5(3) . . ? O1 N4 C12 118.5(3) . . ? O2 N4 C12 118.0(3) . . ? N1 C1 C2 106.3(2) . . ? C1 C2 N3 106.4(2) . . ? C1 C2 C3 135.0(2) . . ? N3 C2 C3 118.6(2) . . ? C8 C3 C4 116.5(3) . . ? C8 C3 C2 126.3(3) . . ? C4 C3 C2 117.2(3) . . ? C5 C4 C3 121.5(3) . . ? C6 C5 C4 120.5(4) . . ? C7 C6 C5 119.5(3) . . ? C6 C7 C8 119.9(3) . . ? C7 C8 C3 122.1(3) . . ? C7 C8 Br1' 114.8(4) . . ? C3 C8 Br1' 121.0(3) . . ? C7 C8 Br1 116.0(3) . . ? C3 C8 Br1 121.8(2) . . ? Br1' C8 Br1 17.9(2) . . ? C10 C9 C14 121.0(2) . . ? C10 C9 N1 119.4(2) . . ? C14 C9 N1 119.6(2) . . ? C11 C10 C9 119.1(2) . . ? C10 C11 C12 119.5(2) . . ? C11 C12 C13 122.1(3) . . ? C11 C12 N4 118.4(3) . . ? C13 C12 N4 119.5(3) . . ? C14 C13 C12 118.4(3) . . ? C13 C14 C9 119.8(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 C1 N1 N2 N3 -0.2(3) . . . . ? C9 N1 N2 N3 179.7(2) . . . . ? N1 N2 N3 C2 0.0(3) . . . . ? N2 N1 C1 C2 0.3(3) . . . . ? C9 N1 C1 C2 -179.6(3) . . . . ? N1 C1 C2 N3 -0.3(3) . . . . ? N1 C1 C2 C3 177.9(3) . . . . ? N2 N3 C2 C1 0.1(3) . . . . ? N2 N3 C2 C3 -178.4(2) . . . . ? C1 C2 C3 C8 -2.7(5) . . . . ? N3 C2 C3 C8 175.3(3) . . . . ? C1 C2 C3 C4 178.3(3) . . . . ? N3 C2 C3 C4 -3.7(4) . . . . ? C8 C3 C4 C5 -0.7(5) . . . . ? C2 C3 C4 C5 178.5(4) . . . . ? C3 C4 C5 C6 -0.3(7) . . . . ? C4 C5 C6 C7 1.8(7) . . . . ? C5 C6 C7 C8 -2.3(6) . . . . ? C6 C7 C8 C3 1.3(5) . . . . ? C6 C7 C8 Br1' 165.0(4) . . . . ? C6 C7 C8 Br1 -175.2(3) . . . . ? C4 C3 C8 C7 0.2(5) . . . . ? C2 C3 C8 C7 -178.9(3) . . . . ? C4 C3 C8 Br1' -162.5(3) . . . . ? C2 C3 C8 Br1' 18.4(5) . . . . ? C4 C3 C8 Br1 176.4(2) . . . . ? C2 C3 C8 Br1 -2.6(4) . . . . ? C1 N1 C9 C10 -23.7(4) . . . . ? N2 N1 C9 C10 156.4(2) . . . . ? C1 N1 C9 C14 155.8(3) . . . . ? N2 N1 C9 C14 -24.2(4) . . . . ? C14 C9 C10 C11 -0.8(4) . . . . ? N1 C9 C10 C11 178.6(2) . . . . ? C9 C10 C11 C12 -0.4(4) . . . . ? C10 C11 C12 C13 1.6(4) . . . . ? C10 C11 C12 N4 -177.9(2) . . . . ? O1 N4 C12 C11 179.5(3) . . . . ? O2 N4 C12 C11 -0.7(4) . . . . ? O1 N4 C12 C13 -0.1(4) . . . . ? O2 N4 C12 C13 179.7(3) . . . . ? C11 C12 C13 C14 -1.6(4) . . . . ? N4 C12 C13 C14 177.9(2) . . . . ? C12 C13 C14 C9 0.4(4) . . . . ? C10 C9 C14 C13 0.8(4) . . . . ? N1 C9 C14 C13 -178.6(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 C11 H11 N2 0.93 2.56 3.231(4) 129.5 6_565 C6 H6 O1 0.93 2.62 3.321(5) 132.3 8_556 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.314 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.068 #===END data_18 _database_code_depnum_ccdc_archive 'CCDC 679566' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 Br N4 O2' _chemical_formula_sum 'C14 H9 Br N4 O2' _chemical_formula_weight 345.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'p 21/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 7.5222(8) _cell_length_b 14.1697(15) _cell_length_c 13.0479(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.391(2) _cell_angle_gamma 90.00 _cell_volume 1390.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 2112 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 23.88 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.88 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 2.965 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1800 _exptl_absorpt_correction_T_max 0.7888 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7835 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2434 _reflns_number_gt 1859 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0487P)^2^+0.6891P] 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_number_reflns 2434 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0547 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1033 _refine_ls_wR_factor_gt 0.0958 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 0.73011(7) 0.08413(3) 0.54878(3) 0.0877(2) Uani 1 1 d . . . O1 O 0.9805(4) 0.95279(19) 0.6997(2) 0.0882(8) Uani 1 1 d . . . O2 O 1.0472(3) 0.85450(18) 0.81932(18) 0.0741(7) Uani 1 1 d . . . N1 N 0.7483(3) 0.57385(15) 0.48822(17) 0.0396(5) Uani 1 1 d . . . N2 N 0.6644(4) 0.59087(17) 0.39803(18) 0.0534(7) Uani 1 1 d . . . N3 N 0.6213(3) 0.50940(18) 0.35888(18) 0.0544(6) Uani 1 1 d . . . N4 N 0.9887(4) 0.8730(2) 0.7343(2) 0.0594(7) Uani 1 1 d . . . C1 C 0.7567(4) 0.48031(19) 0.5053(2) 0.0424(6) Uani 1 1 d . . . H1 H 0.8071 0.4502 0.5618 0.051 Uiso 1 1 calc R . . C2 C 0.6765(4) 0.43896(19) 0.4234(2) 0.0408(6) Uani 1 1 d . . . C3 C 0.6475(3) 0.3385(2) 0.4005(2) 0.0432(7) Uani 1 1 d . . . C4 C 0.5778(4) 0.3104(2) 0.3063(2) 0.0555(8) Uani 1 1 d . . . H4 H 0.5481 0.3554 0.2573 0.067 Uiso 1 1 calc R . . C5 C 0.5527(4) 0.2157(3) 0.2855(3) 0.0646(9) Uani 1 1 d . . . H5 H 0.5058 0.1977 0.2223 0.078 Uiso 1 1 calc R . . C6 C 0.5955(4) 0.1476(2) 0.3562(3) 0.0624(9) Uani 1 1 d . . . H6 H 0.5785 0.0840 0.3417 0.075 Uiso 1 1 calc R . . C7 C 0.6645(4) 0.1759(2) 0.4497(2) 0.0548(8) Uani 1 1 d . . . C8 C 0.6896(4) 0.2702(2) 0.4726(2) 0.0465(7) Uani 1 1 d . . . H8 H 0.7347 0.2877 0.5364 0.056 Uiso 1 1 calc R . . C9 C 0.8093(3) 0.64938(18) 0.55042(19) 0.0388(6) Uani 1 1 d . . . C10 C 0.8796(4) 0.6309(2) 0.6466(2) 0.0465(7) Uani 1 1 d . . . H10 H 0.8867 0.5691 0.6705 0.056 Uiso 1 1 calc R . . C11 C 0.9392(4) 0.7045(2) 0.7071(2) 0.0502(7) Uani 1 1 d . . . H11 H 0.9880 0.6931 0.7716 0.060 Uiso 1 1 calc R . . C12 C 0.9251(4) 0.7948(2) 0.6701(2) 0.0460(7) Uani 1 1 d . . . C13 C 0.8557(4) 0.8144(2) 0.5744(2) 0.0518(7) Uani 1 1 d . . . H13 H 0.8484 0.8763 0.5510 0.062 Uiso 1 1 calc R . . C14 C 0.7978(4) 0.7414(2) 0.5145(2) 0.0471(7) Uani 1 1 d . . . H14 H 0.7506 0.7533 0.4497 0.057 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 0.1329(4) 0.0404(2) 0.0898(3) 0.00560(17) -0.0015(3) -0.0011(2) O1 0.129(2) 0.0466(15) 0.0888(18) -0.0172(14) -0.0241(16) -0.0047(15) O2 0.0840(17) 0.0776(18) 0.0603(15) -0.0237(12) -0.0214(13) -0.0003(13) N1 0.0447(13) 0.0380(13) 0.0360(12) 0.0022(10) -0.0081(9) -0.0005(10) N2 0.0711(17) 0.0446(15) 0.0443(14) 0.0051(11) -0.0208(12) -0.0032(12) N3 0.0682(16) 0.0478(15) 0.0468(14) 0.0007(12) -0.0177(12) -0.0033(13) N4 0.0600(16) 0.0555(18) 0.0625(18) -0.0196(14) -0.0053(13) 0.0004(14) C1 0.0492(16) 0.0329(15) 0.0450(15) 0.0004(12) -0.0100(12) 0.0025(12) C2 0.0385(15) 0.0422(16) 0.0415(15) -0.0013(12) -0.0067(12) 0.0016(12) C3 0.0392(15) 0.0434(17) 0.0470(16) -0.0106(13) -0.0012(12) -0.0018(12) C4 0.0571(19) 0.057(2) 0.0522(17) -0.0105(15) -0.0108(14) -0.0011(15) C5 0.064(2) 0.069(2) 0.060(2) -0.0284(18) -0.0101(16) -0.0059(17) C6 0.062(2) 0.0490(19) 0.076(2) -0.0230(18) 0.0018(17) -0.0100(16) C7 0.0591(19) 0.0402(17) 0.065(2) -0.0073(15) 0.0032(15) -0.0024(14) C8 0.0512(17) 0.0404(17) 0.0477(16) -0.0064(13) -0.0044(13) -0.0036(13) C9 0.0402(15) 0.0348(14) 0.0413(14) -0.0017(12) -0.0061(11) 0.0011(12) C10 0.0554(17) 0.0382(16) 0.0457(16) 0.0013(13) -0.0100(13) 0.0017(13) C11 0.0545(18) 0.0529(19) 0.0430(15) -0.0049(14) -0.0121(13) 0.0039(14) C12 0.0472(16) 0.0406(17) 0.0503(17) -0.0111(13) -0.0033(13) 0.0014(13) C13 0.0646(19) 0.0373(16) 0.0533(17) -0.0014(14) -0.0065(14) 0.0023(14) C14 0.0597(18) 0.0384(16) 0.0432(15) 0.0019(13) -0.0130(13) 0.0008(14) _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 C7 1.897(3) . ? O1 N4 1.218(4) . ? O2 N4 1.220(3) . ? N1 C1 1.346(3) . ? N1 N2 1.353(3) . ? N1 C9 1.418(3) . ? N2 N3 1.303(3) . ? N3 C2 1.368(4) . ? N4 C12 1.467(4) . ? C1 C2 1.357(4) . ? C2 C3 1.470(4) . ? C3 C8 1.386(4) . ? C3 C4 1.391(4) . ? C4 C5 1.382(5) . ? C5 C6 1.372(5) . ? C6 C7 1.382(4) . ? C7 C8 1.381(4) . ? C9 C10 1.384(4) . ? C9 C14 1.388(4) . ? C10 C11 1.381(4) . ? C11 C12 1.372(4) . ? C12 C13 1.378(4) . ? C13 C14 1.366(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 C1 N1 N2 109.9(2) . . ? C1 N1 C9 129.3(2) . . ? N2 N1 C9 120.7(2) . . ? N3 N2 N1 107.3(2) . . ? N2 N3 C2 109.4(2) . . ? O1 N4 O2 123.6(3) . . ? O1 N4 C12 118.3(3) . . ? O2 N4 C12 118.1(3) . . ? N1 C1 C2 105.9(2) . . ? C1 C2 N3 107.5(2) . . ? C1 C2 C3 130.0(2) . . ? N3 C2 C3 122.5(2) . . ? C8 C3 C4 118.8(3) . . ? C8 C3 C2 120.4(2) . . ? C4 C3 C2 120.8(3) . . ? C5 C4 C3 120.2(3) . . ? C6 C5 C4 121.3(3) . . ? C5 C6 C7 118.3(3) . . ? C8 C7 C6 121.5(3) . . ? C8 C7 Br1 118.7(2) . . ? C6 C7 Br1 119.8(2) . . ? C7 C8 C3 119.9(3) . . ? C10 C9 C14 120.5(2) . . ? C10 C9 N1 119.8(2) . . ? C14 C9 N1 119.8(2) . . ? C11 C10 C9 119.7(3) . . ? C12 C11 C10 118.7(3) . . ? C11 C12 C13 122.3(3) . . ? C11 C12 N4 118.7(3) . . ? C13 C12 N4 119.0(3) . . ? C14 C13 C12 118.9(3) . . ? C13 C14 C9 119.9(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 C1 N1 N2 N3 -0.2(3) . . . . ? C9 N1 N2 N3 -178.9(2) . . . . ? N1 N2 N3 C2 0.1(3) . . . . ? N2 N1 C1 C2 0.2(3) . . . . ? C9 N1 C1 C2 178.8(3) . . . . ? N1 C1 C2 N3 -0.2(3) . . . . ? N1 C1 C2 C3 179.8(3) . . . . ? N2 N3 C2 C1 0.1(3) . . . . ? N2 N3 C2 C3 -179.9(3) . . . . ? C1 C2 C3 C8 6.5(5) . . . . ? N3 C2 C3 C8 -173.5(3) . . . . ? C1 C2 C3 C4 -173.3(3) . . . . ? N3 C2 C3 C4 6.7(4) . . . . ? C8 C3 C4 C5 -0.4(4) . . . . ? C2 C3 C4 C5 179.4(3) . . . . ? C3 C4 C5 C6 -0.1(5) . . . . ? C4 C5 C6 C7 0.2(5) . . . . ? C5 C6 C7 C8 0.3(5) . . . . ? C5 C6 C7 Br1 -178.7(2) . . . . ? C6 C7 C8 C3 -0.9(5) . . . . ? Br1 C7 C8 C3 178.2(2) . . . . ? C4 C3 C8 C7 0.9(4) . . . . ? C2 C3 C8 C7 -178.9(3) . . . . ? C1 N1 C9 C10 -4.5(4) . . . . ? N2 N1 C9 C10 173.9(3) . . . . ? C1 N1 C9 C14 175.6(3) . . . . ? N2 N1 C9 C14 -5.9(4) . . . . ? C14 C9 C10 C11 -0.2(4) . . . . ? N1 C9 C10 C11 179.9(3) . . . . ? C9 C10 C11 C12 0.7(4) . . . . ? C10 C11 C12 C13 -0.9(4) . . . . ? C10 C11 C12 N4 -179.9(3) . . . . ? O1 N4 C12 C11 177.9(3) . . . . ? O2 N4 C12 C11 -2.0(4) . . . . ? O1 N4 C12 C13 -1.2(4) . . . . ? O2 N4 C12 C13 178.9(3) . . . . ? C11 C12 C13 C14 0.5(5) . . . . ? N4 C12 C13 C14 179.5(3) . . . . ? C12 C13 C14 C9 0.0(5) . . . . ? C10 C9 C14 C13 -0.1(5) . . . . ? N1 C9 C14 C13 179.7(3) . . . . ? 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 C5 H5 N2 0.93 2.52 3.387(4) 154.6 2_645 C1 H1 O2 0.93 2.33 3.247(3) 169.3 2_746 C8 H8 O2 0.93 2.66 3.556(4) 161.2 2_746 C10 H10 O1 0.93 2.56 3.387(4) 148.0 2_746 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.489 _refine_diff_density_min -0.444 _refine_diff_density_rms 0.057 #===END data_19 _database_code_depnum_ccdc_archive 'CCDC 679567' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 Br N4 O2' _chemical_formula_sum 'C14 H9 Br N4 O2' _chemical_formula_weight 345.16 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 9.6141(15) _cell_length_b 12.0915(19) _cell_length_c 12.900(2) _cell_angle_alpha 87.535(2) _cell_angle_beta 71.407(2) _cell_angle_gamma 76.183(2) _cell_volume 1379.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 3651 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 23.53 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.82 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.662 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 2.990 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1930 _exptl_absorpt_correction_T_max 0.7155 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13109 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4834 _reflns_number_gt 3401 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0748P)^2^+0.1560P] 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_number_reflns 4834 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0674 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1284 _refine_ls_wR_factor_gt 0.1159 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 -0.29941(5) 0.01074(4) 0.49306(4) 0.0885(2) Uani 1 1 d . . . O1 O 0.9720(4) 0.2627(3) -0.3609(3) 0.1067(11) Uani 1 1 d . . . O2 O 1.0098(4) 0.2847(3) -0.2122(3) 0.1015(10) Uani 1 1 d . . . N1 N 0.3989(3) 0.1325(2) -0.0348(2) 0.0492(7) Uani 1 1 d . . . N2 N 0.3133(4) 0.1042(3) -0.0900(3) 0.0741(9) Uani 1 1 d . . . N3 N 0.1946(4) 0.0827(3) -0.0175(3) 0.0742(9) Uani 1 1 d . . . N4 N 0.9383(4) 0.2610(3) -0.2660(4) 0.0756(9) Uani 1 1 d . . . C1 C 0.3311(4) 0.1288(3) 0.0732(3) 0.0508(8) Uani 1 1 d . . . H1 H 0.3661 0.1448 0.1289 0.061 Uiso 1 1 calc R . . C2 C 0.2003(4) 0.0968(3) 0.0848(3) 0.0484(8) Uani 1 1 d . . . C3 C 0.0807(4) 0.0786(3) 0.1831(3) 0.0496(8) Uani 1 1 d . . . C4 C -0.0345(4) 0.0315(3) 0.1737(3) 0.0631(10) Uani 1 1 d . . . H4 H -0.0357 0.0133 0.1047 0.076 Uiso 1 1 calc R . . C5 C -0.1463(4) 0.0116(3) 0.2658(3) 0.0681(10) Uani 1 1 d . . . H5 H -0.2221 -0.0201 0.2588 0.082 Uiso 1 1 calc R . . C6 C -0.1455(4) 0.0388(3) 0.3675(3) 0.0598(9) Uani 1 1 d . . . C7 C -0.0329(4) 0.0867(3) 0.3791(3) 0.0613(9) Uani 1 1 d . . . H7 H -0.0328 0.1059 0.4481 0.074 Uiso 1 1 calc R . . C8 C 0.0779(4) 0.1051(3) 0.2869(3) 0.0574(9) Uani 1 1 d . . . H8 H 0.1536 0.1366 0.2946 0.069 Uiso 1 1 calc R . . C9 C 0.5361(4) 0.1631(3) -0.0929(3) 0.0482(8) Uani 1 1 d . . . C10 C 0.6137(4) 0.2037(3) -0.0358(3) 0.0597(9) Uani 1 1 d . . . H10 H 0.5774 0.2099 0.0402 0.072 Uiso 1 1 calc R . . C11 C 0.7466(4) 0.2354(3) -0.0926(3) 0.0656(10) Uani 1 1 d . . . H11 H 0.8004 0.2624 -0.0551 0.079 Uiso 1 1 calc R . . C12 C 0.7970(4) 0.2264(3) -0.2037(3) 0.0605(9) Uani 1 1 d . . . C13 C 0.7203(4) 0.1851(3) -0.2625(3) 0.0594(9) Uani 1 1 d . . . H13 H 0.7566 0.1795 -0.3385 0.071 Uiso 1 1 calc R . . C14 C 0.5894(4) 0.1526(3) -0.2057(3) 0.0572(9) Uani 1 1 d . . . H14 H 0.5371 0.1236 -0.2433 0.069 Uiso 1 1 calc R . . Br1' Br -0.00865(5) 0.41132(4) 1.38440(3) 0.08024(19) Uani 1 1 d . . . O1' O 0.6719(4) 0.2692(3) 0.2096(3) 0.0960(10) Uani 1 1 d . . . O2' O 0.4691(5) 0.2081(4) 0.2520(3) 0.1208(13) Uani 1 1 d . . . N1' N 0.4036(3) 0.3961(2) 0.7148(2) 0.0498(7) Uani 1 1 d . . . N2' N 0.4932(4) 0.4508(3) 0.7460(3) 0.0654(8) Uani 1 1 d . . . N3' N 0.4374(4) 0.4659(3) 0.8520(3) 0.0649(8) Uani 1 1 d . . . N4' N 0.5546(5) 0.2550(3) 0.2756(3) 0.0793(10) Uani 1 1 d . . . C1' C 0.2920(4) 0.3770(3) 0.8026(3) 0.0520(8) Uani 1 1 d . . . H1' H 0.2163 0.3411 0.8031 0.062 Uiso 1 1 calc R . . C2' C 0.3126(4) 0.4211(3) 0.8908(3) 0.0501(8) Uani 1 1 d . . . C3' C 0.2313(4) 0.4204(3) 1.0084(3) 0.0497(8) Uani 1 1 d . . . C4' C 0.2924(4) 0.4509(3) 1.0841(3) 0.0590(9) Uani 1 1 d . . . H4' H 0.3831 0.4734 1.0595 0.071 Uiso 1 1 calc R . . C5' C 0.2213(4) 0.4484(3) 1.1943(3) 0.0638(10) Uani 1 1 d . . . H5' H 0.2633 0.4695 1.2440 0.077 Uiso 1 1 calc R . . C6' C 0.0873(4) 0.4146(3) 1.2312(3) 0.0564(9) Uani 1 1 d . . . C7' C 0.0237(4) 0.3837(3) 1.1571(3) 0.0559(9) Uani 1 1 d . . . H7' H -0.0672 0.3615 1.1821 0.067 Uiso 1 1 calc R . . C8' C 0.0962(4) 0.3863(3) 1.0472(3) 0.0542(8) Uani 1 1 d . . . H8' H 0.0544 0.3648 0.9977 0.065 Uiso 1 1 calc R . . C9' C 0.4415(4) 0.3622(3) 0.6034(3) 0.0513(8) Uani 1 1 d . . . C10' C 0.3370(4) 0.3260(3) 0.5685(3) 0.0649(10) Uani 1 1 d . . . H10' H 0.2422 0.3253 0.6173 0.078 Uiso 1 1 calc R . . C11' C 0.3750(5) 0.2908(4) 0.4604(3) 0.0692(10) Uani 1 1 d . . . H11' H 0.3060 0.2663 0.4359 0.083 Uiso 1 1 calc R . . C12' C 0.5151(4) 0.2925(3) 0.3899(3) 0.0626(9) Uani 1 1 d . . . C13' C 0.6193(4) 0.3297(3) 0.4226(3) 0.0619(9) Uani 1 1 d . . . H13' H 0.7129 0.3322 0.3729 0.074 Uiso 1 1 calc R . . C14' C 0.5825(4) 0.3634(3) 0.5310(3) 0.0609(9) Uani 1 1 d . . . H14' H 0.6525 0.3868 0.5553 0.073 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 0.0715(3) 0.1130(4) 0.0831(3) 0.0106(3) -0.0107(2) -0.0458(3) O1 0.083(2) 0.143(3) 0.091(3) 0.024(2) -0.0042(19) -0.058(2) O2 0.0651(19) 0.127(3) 0.122(3) 0.000(2) -0.0228(19) -0.0492(19) N1 0.0471(16) 0.0589(17) 0.0492(17) -0.0013(12) -0.0199(13) -0.0196(13) N2 0.075(2) 0.117(3) 0.0553(19) 0.0022(17) -0.0268(17) -0.060(2) N3 0.075(2) 0.109(3) 0.061(2) 0.0042(17) -0.0297(17) -0.055(2) N4 0.056(2) 0.076(2) 0.096(3) 0.001(2) -0.022(2) -0.0207(18) C1 0.051(2) 0.058(2) 0.052(2) 0.0009(15) -0.0229(16) -0.0191(16) C2 0.053(2) 0.0494(18) 0.054(2) 0.0035(14) -0.0252(16) -0.0224(15) C3 0.0487(19) 0.0495(18) 0.059(2) 0.0032(15) -0.0247(16) -0.0181(15) C4 0.059(2) 0.079(2) 0.065(2) 0.0020(19) -0.0275(19) -0.030(2) C5 0.059(2) 0.079(3) 0.080(3) 0.007(2) -0.029(2) -0.034(2) C6 0.050(2) 0.062(2) 0.070(2) 0.0084(18) -0.0170(18) -0.0210(17) C7 0.061(2) 0.072(2) 0.057(2) 0.0003(18) -0.0201(18) -0.0256(19) C8 0.054(2) 0.064(2) 0.066(2) 0.0037(17) -0.0251(18) -0.0296(18) C9 0.0425(18) 0.0518(19) 0.054(2) 0.0014(15) -0.0172(15) -0.0147(15) C10 0.059(2) 0.075(2) 0.055(2) -0.0021(18) -0.0230(17) -0.0272(19) C11 0.058(2) 0.076(3) 0.075(3) -0.004(2) -0.028(2) -0.028(2) C12 0.046(2) 0.062(2) 0.076(3) 0.0061(18) -0.0164(18) -0.0202(17) C13 0.057(2) 0.068(2) 0.050(2) -0.0004(17) -0.0129(17) -0.0150(18) C14 0.054(2) 0.064(2) 0.059(2) -0.0032(17) -0.0231(17) -0.0176(17) Br1' 0.0744(3) 0.1052(4) 0.0573(3) -0.0180(2) -0.0039(2) -0.0338(2) O1' 0.093(2) 0.123(3) 0.0634(19) -0.0051(17) -0.0146(17) -0.021(2) O2' 0.126(3) 0.186(4) 0.077(2) -0.020(2) -0.042(2) -0.069(3) N1' 0.0447(15) 0.0607(17) 0.0542(17) 0.0061(13) -0.0211(13) -0.0251(13) N2' 0.071(2) 0.085(2) 0.0575(19) 0.0086(15) -0.0247(16) -0.0481(18) N3' 0.070(2) 0.081(2) 0.061(2) 0.0074(16) -0.0245(16) -0.0448(17) N4' 0.084(3) 0.096(3) 0.062(2) -0.0009(19) -0.033(2) -0.016(2) C1' 0.0414(18) 0.064(2) 0.061(2) 0.0041(17) -0.0237(16) -0.0225(16) C2' 0.0443(18) 0.0536(19) 0.058(2) 0.0052(15) -0.0211(16) -0.0158(15) C3' 0.0454(19) 0.0483(18) 0.059(2) 0.0020(15) -0.0201(16) -0.0123(15) C4' 0.051(2) 0.074(2) 0.061(2) -0.0058(17) -0.0184(18) -0.0290(18) C5' 0.059(2) 0.074(2) 0.064(2) -0.0136(19) -0.0199(19) -0.0233(19) C6' 0.054(2) 0.058(2) 0.055(2) -0.0088(16) -0.0125(17) -0.0134(17) C7' 0.0418(19) 0.063(2) 0.064(2) 0.0038(17) -0.0144(17) -0.0185(16) C8' 0.048(2) 0.060(2) 0.062(2) 0.0012(16) -0.0265(17) -0.0157(16) C9' 0.0497(19) 0.060(2) 0.053(2) 0.0114(16) -0.0237(16) -0.0209(16) C10' 0.053(2) 0.089(3) 0.065(3) 0.009(2) -0.0256(19) -0.031(2) C11' 0.067(3) 0.092(3) 0.064(3) 0.004(2) -0.035(2) -0.029(2) C12' 0.068(2) 0.072(2) 0.052(2) 0.0065(17) -0.0267(19) -0.016(2) C13' 0.052(2) 0.081(3) 0.058(2) 0.0053(18) -0.0169(17) -0.0266(19) C14' 0.054(2) 0.078(2) 0.064(2) 0.0090(19) -0.0272(18) -0.0315(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 Br1 C6 1.895(4) . ? O1 N4 1.163(5) . ? O2 N4 1.206(5) . ? N1 C1 1.340(4) . ? N1 N2 1.353(4) . ? N1 C9 1.421(4) . ? N2 N3 1.299(4) . ? N3 C2 1.357(4) . ? N4 C12 1.488(5) . ? C1 C2 1.365(4) . ? C2 C3 1.465(5) . ? C3 C8 1.380(5) . ? C3 C4 1.400(5) . ? C4 C5 1.383(5) . ? C5 C6 1.369(6) . ? C6 C7 1.394(5) . ? C7 C8 1.371(5) . ? C9 C10 1.376(5) . ? C9 C14 1.380(5) . ? C10 C11 1.389(5) . ? C11 C12 1.359(5) . ? C12 C13 1.389(5) . ? C13 C14 1.377(5) . ? Br1' C6' 1.898(4) . ? O1' N4' 1.222(5) . ? O2' N4' 1.219(5) . ? N1' C1' 1.345(4) . ? N1' N2' 1.363(4) . ? N1' C9' 1.419(4) . ? N2' N3' 1.303(4) . ? N3' C2' 1.375(4) . ? N4' C12' 1.464(5) . ? C1' C2' 1.365(5) . ? C2' C3' 1.469(5) . ? C3' C8' 1.390(5) . ? C3' C4' 1.392(5) . ? C4' C5' 1.369(5) . ? C5' C6' 1.378(5) . ? C6' C7' 1.393(5) . ? C7' C8' 1.368(5) . ? C9' C14' 1.382(5) . ? C9' C10' 1.385(5) . ? C10' C11' 1.382(5) . ? C11' C12' 1.369(5) . ? C12' C13' 1.373(5) . ? C13' C14' 1.382(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 N1 N2 109.8(3) . . ? C1 N1 C9 130.1(3) . . ? N2 N1 C9 120.0(3) . . ? N3 N2 N1 107.0(3) . . ? N2 N3 C2 110.1(3) . . ? O1 N4 O2 125.2(4) . . ? O1 N4 C12 118.9(4) . . ? O2 N4 C12 116.0(4) . . ? N1 C1 C2 106.1(3) . . ? N3 C2 C1 107.0(3) . . ? N3 C2 C3 122.2(3) . . ? C1 C2 C3 130.8(3) . . ? C8 C3 C4 117.9(3) . . ? C8 C3 C2 122.1(3) . . ? C4 C3 C2 120.0(3) . . ? C5 C4 C3 120.6(4) . . ? C6 C5 C4 119.9(4) . . ? C5 C6 C7 120.5(3) . . ? C5 C6 Br1 119.4(3) . . ? C7 C6 Br1 120.1(3) . . ? C8 C7 C6 118.8(3) . . ? C7 C8 C3 122.2(3) . . ? C10 C9 C14 120.9(3) . . ? C10 C9 N1 119.4(3) . . ? C14 C9 N1 119.7(3) . . ? C9 C10 C11 119.5(4) . . ? C12 C11 C10 119.2(3) . . ? C11 C12 C13 121.9(3) . . ? C11 C12 N4 120.0(4) . . ? C13 C12 N4 118.1(4) . . ? C14 C13 C12 118.6(3) . . ? C13 C14 C9 119.8(3) . . ? C1' N1' N2' 110.3(3) . . ? C1' N1' C9' 129.8(3) . . ? N2' N1' C9' 119.8(3) . . ? N3' N2' N1' 106.8(3) . . ? N2' N3' C2' 109.9(3) . . ? O2' N4' O1' 123.4(4) . . ? O2' N4' C12' 117.5(4) . . ? O1' N4' C12' 119.2(4) . . ? N1' C1' C2' 105.9(3) . . ? C1' C2' N3' 107.2(3) . . ? C1' C2' C3' 130.9(3) . . ? N3' C2' C3' 121.8(3) . . ? C8' C3' C4' 118.3(3) . . ? C8' C3' C2' 121.9(3) . . ? C4' C3' C2' 119.7(3) . . ? C5' C4' C3' 121.2(3) . . ? C4' C5' C6' 119.6(3) . . ? C5' C6' C7' 120.3(3) . . ? C5' C6' Br1' 118.8(3) . . ? C7' C6' Br1' 120.9(3) . . ? C8' C7' C6' 119.4(3) . . ? C7' C8' C3' 121.2(3) . . ? C14' C9' C10' 120.5(3) . . ? C14' C9' N1' 120.1(3) . . ? C10' C9' N1' 119.4(3) . . ? C11' C10' C9' 119.4(4) . . ? C12' C11' C10' 119.4(4) . . ? C11' C12' C13' 122.1(4) . . ? C11' C12' N4' 119.1(4) . . ? C13' C12' N4' 118.9(4) . . ? C12' C13' C14' 118.7(3) . . ? C9' C14' C13' 120.0(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 C1 N1 N2 N3 -0.4(4) . . . . ? C9 N1 N2 N3 -178.7(3) . . . . ? N1 N2 N3 C2 0.3(4) . . . . ? N2 N1 C1 C2 0.3(4) . . . . ? C9 N1 C1 C2 178.4(3) . . . . ? N2 N3 C2 C1 -0.1(4) . . . . ? N2 N3 C2 C3 179.8(3) . . . . ? N1 C1 C2 N3 -0.1(4) . . . . ? N1 C1 C2 C3 180.0(3) . . . . ? N3 C2 C3 C8 -172.6(3) . . . . ? C1 C2 C3 C8 7.3(6) . . . . ? N3 C2 C3 C4 8.3(5) . . . . ? C1 C2 C3 C4 -171.9(4) . . . . ? C8 C3 C4 C5 -0.5(5) . . . . ? C2 C3 C4 C5 178.7(3) . . . . ? C3 C4 C5 C6 0.4(6) . . . . ? C4 C5 C6 C7 0.2(6) . . . . ? C4 C5 C6 Br1 -179.8(3) . . . . ? C5 C6 C7 C8 -0.6(6) . . . . ? Br1 C6 C7 C8 179.4(3) . . . . ? C6 C7 C8 C3 0.5(5) . . . . ? C4 C3 C8 C7 0.1(5) . . . . ? C2 C3 C8 C7 -179.1(3) . . . . ? C1 N1 C9 C10 -5.1(5) . . . . ? N2 N1 C9 C10 172.9(3) . . . . ? C1 N1 C9 C14 175.3(3) . . . . ? N2 N1 C9 C14 -6.7(5) . . . . ? C14 C9 C10 C11 0.6(5) . . . . ? N1 C9 C10 C11 -179.0(3) . . . . ? C9 C10 C11 C12 0.4(6) . . . . ? C10 C11 C12 C13 -0.7(6) . . . . ? C10 C11 C12 N4 179.4(3) . . . . ? O1 N4 C12 C11 -172.9(4) . . . . ? O2 N4 C12 C11 7.6(5) . . . . ? O1 N4 C12 C13 7.2(6) . . . . ? O2 N4 C12 C13 -172.3(4) . . . . ? C11 C12 C13 C14 0.0(6) . . . . ? N4 C12 C13 C14 179.9(3) . . . . ? C12 C13 C14 C9 1.0(5) . . . . ? C10 C9 C14 C13 -1.3(5) . . . . ? N1 C9 C14 C13 178.3(3) . . . . ? C1' N1' N2' N3' -0.3(4) . . . . ? C9' N1' N2' N3' -176.5(3) . . . . ? N1' N2' N3' C2' 0.4(4) . . . . ? N2' N1' C1' C2' 0.1(4) . . . . ? C9' N1' C1' C2' 175.8(3) . . . . ? N1' C1' C2' N3' 0.2(4) . . . . ? N1' C1' C2' C3' -176.4(3) . . . . ? N2' N3' C2' C1' -0.4(4) . . . . ? N2' N3' C2' C3' 176.6(3) . . . . ? C1' C2' C3' C8' -10.8(5) . . . . ? N3' C2' C3' C8' 173.1(3) . . . . ? C1' C2' C3' C4' 167.0(3) . . . . ? N3' C2' C3' C4' -9.1(5) . . . . ? C8' C3' C4' C5' -0.5(5) . . . . ? C2' C3' C4' C5' -178.4(3) . . . . ? C3' C4' C5' C6' 0.3(6) . . . . ? C4' C5' C6' C7' -0.4(5) . . . . ? C4' C5' C6' Br1' 179.8(3) . . . . ? C5' C6' C7' C8' 0.6(5) . . . . ? Br1' C6' C7' C8' -179.6(3) . . . . ? C6' C7' C8' C3' -0.7(5) . . . . ? C4' C3' C8' C7' 0.7(5) . . . . ? C2' C3' C8' C7' 178.5(3) . . . . ? C1' N1' C9' C14' -162.4(3) . . . . ? N2' N1' C9' C14' 12.9(5) . . . . ? C1' N1' C9' C10' 16.4(5) . . . . ? N2' N1' C9' C10' -168.2(3) . . . . ? C14' C9' C10' C11' 0.1(6) . . . . ? N1' C9' C10' C11' -178.8(3) . . . . ? C9' C10' C11' C12' -0.1(6) . . . . ? C10' C11' C12' C13' -0.9(6) . . . . ? C10' C11' C12' N4' 179.9(3) . . . . ? O2' N4' C12' C11' -10.5(6) . . . . ? O1' N4' C12' C11' 171.2(4) . . . . ? O2' N4' C12' C13' 170.3(4) . . . . ? O1' N4' C12' C13' -8.0(6) . . . . ? C11' C12' C13' C14' 1.8(6) . . . . ? N4' C12' C13' C14' -179.0(3) . . . . ? C10' C9' C14' C13' 0.9(5) . . . . ? N1' C9' C14' C13' 179.7(3) . . . . ? C12' C13' C14' C9' -1.8(6) . . . . ? 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 C1 H1 O2' 0.93 2.36 3.279(5) 170.9 . C10 H10 O2' 0.93 2.60 3.523(5) 174.4 . C4 H4 N3 0.93 2.65 3.401(5) 138.8 2 C1' H1' O2 0.93 2.31 3.230(5) 168.4 1_456 C10' H10' O2 0.93 2.71 3.620(5) 164.7 1_456 C4' H4' N3' 0.93 2.60 3.334(5) 136.5 2_667 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.856 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.065 #===END