#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/05/2200508.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2200508 loop_ _publ_author_name 'H\"okelek, Tuncer' 'K\?il\?i\,c, Emine' 'Din\,cer, Sebla' _publ_section_title ; 2-Bromobenzo[c]cinnoline 6-oxide ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o645 _journal_page_last o647 _journal_paper_doi 10.1107/S1600536801010236 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C12 H7 Br N2 O' _chemical_formula_moiety 'C12 H7 Br N2 O' _chemical_formula_sum 'C12 H7 Br N2 O' _chemical_formula_weight 275.10 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 1 21/a 1' _atom_type_scat_source IntTabIV _cell_angle_alpha 90 _cell_angle_beta 98.59(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.446(3) _cell_length_b 3.9630(10) _cell_length_c 17.807(7) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298 _cell_measurement_theta_max 11 _cell_measurement_theta_min 10 _cell_volume 1008.0(5) _computing_cell_refinement MolEN _computing_data_collection 'MolEN (Fair, 1990)' _computing_data_reduction MolEN _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material MolEN _computing_structure_refinement MolEN _computing_structure_solution 'SHELX86 (Sheldrick, 1990)' _diffrn_measured_fraction_theta_full .990 _diffrn_measured_fraction_theta_max .990 _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .014 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2420 _diffrn_reflns_theta_full 26.3 _diffrn_reflns_theta_max 26.3 _diffrn_standards_decay_% 1 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 4.053 _exptl_absorpt_correction_T_max .667 _exptl_absorpt_correction_T_min .621 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details '(Fair, 1990)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.813 _exptl_crystal_density_method none _exptl_crystal_description rod-shaped _exptl_crystal_F_000 544 _exptl_crystal_size_max .30 _exptl_crystal_size_mid .10 _exptl_crystal_size_min .10 _refine_diff_density_max .46 _refine_diff_density_min -.51 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.12 _refine_ls_hydrogen_treatment constr _refine_ls_number_parameters 145 _refine_ls_number_reflns 1764 _refine_ls_R_factor_gt .058 _refine_ls_shift/su_max .01 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'calc w = 1 / [\s(F)^2^ + (0.02 F)^2^ + 1.0] ' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .051 _reflns_number_gt 1764 _reflns_number_total 2031 _reflns_threshold_expression F>0 _cod_data_source_file ob6057.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/a' _cod_database_code 2200508 _cod_database_fobs_code 2200508 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,y+1/2,-z -x,-y,-z x+1/2,-y+1/2,z loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br1 .0526(3) .0628(3) .0505(2) -.0129(3) -.0008(2) -.0069(3) O1 .0260(10) .093(3) .083(2) .004(2) -.003(2) -.010(2) C1 .030(2) .041(2) .038(2) .000(2) .007(2) .005(2) C2 .044(2) .036(2) .039(2) -.006(2) .009(2) .007(2) C3 .056(2) .047(3) .042(2) .000(2) .014(2) -.003(2) C4 .043(2) .048(3) .052(2) .006(2) .019(2) .001(2) C5 .035(2) .036(2) .039(2) .003(2) .013(2) .007(2) N5 .028(2) .057(2) .055(2) .007(2) .010(2) .002(2) N6 .024(2) .052(2) .057(2) .000(2) .006(2) .011(2) C6 .029(2) .042(3) .045(2) -.001(2) .005(2) .010(2) C7 .034(2) .045(3) .048(2) -.008(2) -.006(2) .005(2) C8 .054(3) .049(3) .039(2) -.006(2) .004(2) -.001(2) C9 .041(2) .044(3) .043(2) -.004(2) .012(2) -.001(2) C10 .028(2) .040(2) .039(2) .001(2) .009(2) .007(2) C11 .028(2) .030(2) .035(2) -.001(2) .003(2) .010(2) C12 .031(2) .030(2) .035(2) .002(2) .009(2) .008(2) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv Br1 .59995(4) .45330(10) .06961(3) .0558(3) O1 1.0726(2) .9170(10) .3468(2) .0683(4) C1 .7222(3) .7180(10) .1946(2) .0360(3) C2 .7178(3) .5560(10) .1263(2) .0394(4) C3 .7983(3) .4580(10) .0970(3) .0482(4) C4 .8832(3) .5230(10) .1385(3) .0469(3) C5 .8906(3) .6870(10) .2083(2) .0359(3) N5 .9804(2) .7310(10) .2456(2) .0467(3) N6 .9907(2) .8820(10) .3109(2) .0445(3) C6 .9150(3) 1.0120(10) .3455(2) .0385(3) C7 .9343(3) 1.1710(10) .4156(3) .0436(3) C8 .8623(3) 1.2900(10) .4496(3) .0482(4) C9 .7710(3) 1.2540(10) .4137(2) .0421(5) C10 .7512(3) 1.0960(10) .3448(2) .0356(4) C11 .8234(3) .9660(10) .3086(2) .0309(4) C12 .8100(3) .7930(10) .2368(2) .0313(3) H1 .666 .783 .213 .0431 H3 .793 .346 .049 .0571 H4 .938 .454 .119 .0583 H71 .997 1.197 .440 .0659 H81 .875 1.397 .498 .0659 H91 .721 1.340 .437 .0659 H101 .688 1.075 .321 .0659 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2 C1 C12 119.6(4) no C2 C1 H1 120.1 no C12 C1 H1 120.3 no Br1 C2 C1 119.9(3) ? Br1 C2 C3 118.1(3) ? C1 C2 C3 122.0(4) ? C2 C3 C4 118.7(4) ? C2 C3 H3 120.3 no C4 C3 H3 121.0 no C3 C4 C5 121.1(4) ? C3 C4 H4 119.2 no C5 C4 H4 119.7 no C4 C5 N5 115.6(4) ? C4 C5 C12 120.2(3) no N6 C6 C11 118.7(4) ? C7 C6 C11 122.2(4) ? C6 C7 C8 119.5(4) no C6 C7 H71 119.7 no C8 C7 H71 120.8 no C7 C8 C9 119.7(4) no C7 C8 H81 120.5 no C9 C8 H81 119.9 no C8 C9 C10 121.3(4) no C8 C9 H91 119.5 no C10 C9 H91 119.1 no C9 C10 C11 120.6(3) no C9 C10 H101 119.9 no C11 C10 H101 119.5 no N5 C5 C12 124.2(4) ? C5 N5 N6 117.6(3) ? N5 N6 C6 124.1(3) ? N5 N6 O1 118.5(3) ? C6 N6 O1 117.4(4) ? N6 C6 C7 119.1(3) ? C6 C11 C10 116.7(3) ? C6 C11 C12 118.4(4) ? C10 C11 C12 124.9(3) ? C1 C12 C5 118.5(4) ? C1 C12 C11 124.6(4) ? C5 C12 C11 116.9(3) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Br1 C2 . . 1.892(4) yes N6 O1 . . 1.268(4) yes C12 C5 . . 1.401(6) no C12 C11 . . 1.438(5) no C12 C1 . . 1.404(5) no C5 N5 . . 1.377(5) yes C4 C5 . . 1.393(6) no N5 N6 . . 1.298(5) yes C6 C11 . . 1.397(5) no C6 C7 . . 1.389(6) yes C6 N6 . . 1.426(5) yes C11 C10 . . 1.402(6) no C3 C4 . . 1.359(6) yes C4 H4 . . .950 no C7 C8 . . 1.358(7) yes C7 H71 . . .950 no C1 C2 . . 1.368(6) yes C2 C3 . . 1.396(6) no C3 H3 . . .950 no C9 C10 . . 1.367(6) yes C8 H81 . . .950 no C8 C9 . . 1.386(6) no C1 H1 . . .950 no C10 H101 . . .950 no C9 H91 . . .950 no 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_publ_flag C12 C1 C2 Br1 179.7(3) ? C12 C1 C2 C3 .8(7) no C2 C1 C12 C5 -2.3(6) no C2 C1 C12 C11 179.0(4) no Br1 C2 C3 C4 -178.1(4) ? C1 C2 C3 C4 .9(7) no C2 C3 C4 C5 -.9(7) no C3 C4 C5 N5 178.6(4) no C3 C4 C5 C12 -.7(7) no C4 C5 N5 N6 -179.9(4) no C12 C5 N5 N6 -.7(7) no C4 C5 C12 C1 2.2(6) no C4 C5 C12 C11 -179.0(4) ? N5 C5 C12 C1 -176.9(4) ? N5 C5 C12 C11 1.9(6) no C5 N5 N6 C6 -1.5(6) no C5 N5 N6 O1 178.4(4) ? N5 N6 C6 C7 -179.8(4) no N5 N6 C6 C11 2.4(6) no O1 N6 C6 C7 .3(6) no O1 N6 C6 C11 -177.6(4) ? N6 C6 C7 C8 -178.7(4) no C11 C6 C7 C8 -.9(7) no N6 C6 C11 C10 179.7(4) ? N6 C6 C11 C12 -1.0(6) no C7 C6 C11 C10 1.8(6) no C7 C6 C11 C12 -178.8(4) ? C6 C7 C8 C9 -.5(7) no C7 C8 C9 C10 .8(7) no C8 C9 C10 C11 .1(7) no C9 C10 C11 C6 -1.4(6) no C9 C10 C11 C12 179.3(4) no C6 C11 C12 C1 177.8(4) no C6 C11 C12 C5 -.9(6) no C10 C11 C12 C1 -2.9(7) no C10 C11 C12 C5 178.4(4) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 86111710