#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/16/2011667.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_2011667 loop_ _publ_author_name 'Paix\~ao, J. A.' 'Matos Beja, A.' 'Ramos Silva, M.' 'Alte da Veiga, L.' 'Serra, A.C.' _publ_section_title ; 2,4-Dibromo-3-methoxy-6-nitrobenzaldeyde: effect of substituents on ring geometry ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1501 _journal_page_last 1502 _journal_paper_doi 10.1107/S0108270100012853 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C8 H5 Br2 N1 O4' _chemical_formula_sum 'C8 H5 Br2 N O4' _chemical_formula_weight 338.95 _chemical_melting_point 384 _chemical_name_systematic ; 2,4-dibromo-3-methoxy-6-nitrobenzaldehyde ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 95.847(13) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.3048(10) _cell_length_b 18.108(3) _cell_length_c 13.3152(17) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 15.75 _cell_measurement_theta_min 9.27 _cell_volume 1032.5(3) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'HELENA (Spek, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _computing_structure_refinement SHELXL97 _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .948 _diffrn_measured_fraction_theta_max .948 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method 'profile data from \w-2\q scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .043 _diffrn_reflns_av_sigmaI/netI .061 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 2524 _diffrn_reflns_theta_full 27.47 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_min 3.08 _diffrn_standards_decay_% 4.7 _diffrn_standards_interval_time 180 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 7.843 _exptl_absorpt_correction_T_max .955 _exptl_absorpt_correction_T_min .486 _exptl_absorpt_correction_type \y-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 2.180 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 648 _exptl_crystal_size_max .44 _exptl_crystal_size_mid .22 _exptl_crystal_size_min .17 _refine_diff_density_max .43 _refine_diff_density_min -.58 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .981 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 137 _refine_ls_number_reflns 2255 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .981 _refine_ls_R_factor_all .113 _refine_ls_R_factor_gt .035 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0436P)^2^+1.3920P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .099 _reflns_number_gt 1238 _reflns_number_total 2255 _reflns_threshold_expression I>2\s(I) _cod_data_source_file sk1420.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_original_formula_sum 'C8 H5 Br2 N1 O4' _cod_database_code 2011667 _cod_database_fobs_code 2011667 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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Br1 .35548(13) .41099(3) .05964(4) .0580(2) Uani d . 1 . . Br Br2 -.11415(16) .25205(4) .37595(5) .0764(2) Uani d . 1 . . Br O1 .4495(9) .5668(2) .1683(3) .0725(12) Uani d . 1 . . O O2 .0279(11) .5964(2) .3504(4) .0887(14) Uani d . 1 . . O O3 -.2975(11) .5376(3) .4320(3) .0831(13) Uani d . 1 . . O O4 .1957(8) .28069(19) .1807(3) .0566(9) Uani d . 1 . . O N1 -.1103(11) .5408(3) .3706(3) .0566(11) Uani d . 1 . . N C1 .1137(11) .4779(3) .2296(3) .0410(11) Uani d . 1 . . C C2 .1789(10) .4115(3) .1844(3) .0393(10) Uani d . 1 . . C C3 .1095(11) .3429(3) .2252(4) .0410(11) Uani d . 1 . . C C4 -.0362(12) .3428(3) .3149(4) .0490(13) Uani d . 1 . . C C5 -.1129(11) .4072(3) .3600(3) .0495(12) Uani d . 1 . . C H5 -.2152 .4064 .4183 .059 Uiso calc R 1 . . H C6 -.0364(11) .4724(3) .3179(4) .0448(12) Uani d . 1 . . C C7 .1899(13) .5503(3) .1842(4) .0531(13) Uani d . 1 . . C H7 .0292 .5838 .1676 .064 Uiso calc R 1 . . H C8 -.0426(14) .2390(3) .1242(5) .0749(18) Uani d . 1 . . C H8A -.2197 .2347 .1622 .112 Uiso calc R 1 . . H H8B .0353 .1907 .1109 .112 Uiso calc R 1 . . H H8C -.1041 .2637 .0615 .112 Uiso calc R 1 . . H 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 .0590(3) .0597(4) .0588(3) -.0008(3) .0234(2) .0022(3) Br2 .0922(5) .0586(4) .0783(4) -.0171(3) .0079(3) .0285(3) O1 .057(2) .052(2) .111(3) -.009(2) .022(2) .011(2) O2 .083(3) .055(3) .131(4) -.010(3) .027(3) -.025(3) O3 .099(3) .082(3) .073(3) .012(3) .029(3) -.013(2) O4 .051(2) .0405(19) .080(3) .0027(18) .0135(19) -.0077(19) N1 .052(3) .056(3) .061(3) .000(2) .002(2) -.007(2) C1 .037(3) .038(3) .048(3) -.001(2) .002(2) .006(2) C2 .033(2) .042(3) .044(2) .002(2) .0070(18) .003(2) C3 .032(2) .038(3) .052(3) .001(2) -.002(2) .003(2) C4 .047(3) .047(3) .052(3) -.009(2) .002(2) .014(2) C5 .056(3) .051(3) .042(3) -.010(3) .008(2) .002(2) C6 .038(3) .049(3) .047(3) .002(2) .002(2) -.005(2) C7 .047(3) .044(3) .068(4) -.003(3) .005(3) .007(3) C8 .055(4) .063(4) .106(5) .003(3) .006(3) -.032(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C3 O4 C8 117.4(4) ? O3 N1 O2 124.4(5) ? O3 N1 C6 118.3(5) ? O2 N1 C6 117.2(5) ? C2 C1 C6 115.8(4) yes C2 C1 C7 121.5(4) ? C6 C1 C7 122.7(5) ? C1 C2 C3 122.7(4) yes C1 C2 Br1 120.2(3) ? C3 C2 Br1 117.1(3) ? O4 C3 C2 119.5(4) ? O4 C3 C4 122.9(4) ? C2 C3 C4 117.5(4) yes C5 C4 C3 121.5(4) yes C5 C4 Br2 119.6(4) ? C3 C4 Br2 118.9(4) ? C6 C5 C4 118.6(4) yes C6 C5 H5 120.7 ? C4 C5 H5 120.7 ? C5 C6 C1 123.9(5) yes C5 C6 N1 117.4(4) ? C1 C6 N1 118.7(5) ? O1 C7 C1 122.6(5) ? O1 C7 H7 118.7 ? C1 C7 H7 118.7 ? O4 C8 H8A 109.5 ? O4 C8 H8B 109.5 ? H8A C8 H8B 109.5 ? O4 C8 H8C 109.5 ? H8A C8 H8C 109.5 ? H8B C8 H8C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Br1 C2 . 1.896(4) ? Br2 C4 . 1.879(5) ? O1 C7 . 1.196(6) ? O2 N1 . 1.214(6) ? O3 N1 . 1.207(6) ? O4 C3 . 1.342(6) ? O4 C8 . 1.425(7) ? N1 C6 . 1.473(7) ? C1 C2 . 1.386(6) yes C1 C6 . 1.401(6) ? C1 C7 . 1.495(7) ? C2 C3 . 1.402(6) yes C3 C4 . 1.404(7) yes C4 C5 . 1.367(7) yes C5 C6 . 1.363(7) yes C5 H5 . .9300 ? C7 H7 . .9300 ? C8 H8A . .9600 ? C8 H8B . .9600 ? C8 H8C . .9600 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA C7 H7 O1 1_455 .93 2.52 3.187(6) 129.3 C8 H8A Br2 . .96 2.85 3.406(7) 117.5 C8 H8B O2 2_545 .96 2.55 3.397(8) 146.8 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 C6 C1 C2 C3 -2.0(6) ? C7 C1 C2 C3 -179.9(5) ? C6 C1 C2 Br1 175.7(3) ? C7 C1 C2 Br1 -2.2(6) ? C8 O4 C3 C2 -105.6(6) ? C8 O4 C3 C4 77.5(7) yes C1 C2 C3 O4 -176.1(4) ? Br1 C2 C3 O4 6.2(6) ? C1 C2 C3 C4 1.0(7) ? Br1 C2 C3 C4 -176.8(3) ? O4 C3 C4 C5 178.1(5) ? C2 C3 C4 C5 1.1(7) ? O4 C3 C4 Br2 .2(7) ? C2 C3 C4 Br2 -176.8(3) ? C3 C4 C5 C6 -2.0(7) ? Br2 C4 C5 C6 175.9(4) ? C4 C5 C6 C1 .9(7) ? C4 C5 C6 N1 -177.5(4) ? C2 C1 C6 C5 1.1(7) ? C7 C1 C6 C5 178.9(5) ? C2 C1 C6 N1 179.4(4) ? C7 C1 C6 N1 -2.7(7) ? O3 N1 C6 C5 -17.9(7) yes O2 N1 C6 C5 160.6(5) ? O3 N1 C6 C1 163.6(5) ? O2 N1 C6 C1 -17.9(7) ? C2 C1 C7 O1 -58.5(7) yes C6 C1 C7 O1 123.7(6) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21105818 2 PubChem 102016519