#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/60/2006078.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_2006078 loop_ _publ_author_name 'Matos Beja, A.' 'Paix\~ao, J. A.' 'Ramos Silva, M.' 'Alte da Veiga, L.' 'd Rocha Gonsalves, A. M.' 'Pereira, M. M.' 'Serra, A. C.' _publ_section_title ; 2,4-Dibromo-5-hydroxybenzaldehyde ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 494 _journal_page_last 496 _journal_volume 53 _journal_year 1997 _chemical_formula_moiety 'C7 H4 Br2 O2' _chemical_formula_structural 'C7 H4 Br2 O2' _chemical_formula_sum 'C7 H4 Br2 O2' _chemical_formula_weight 279.92 _chemical_melting_point 411.0(10) _chemical_name_systematic ; 2,4-dibromo-5-hydroxybenzaldehyde ; _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 SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 93.20(1) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 3.9851(5) _cell_length_b 16.547(3) _cell_length_c 11.841(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 16.62 _cell_measurement_theta_min 8.33 _cell_volume 779.6(2) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf Nonius, 1989)' _computing_data_reduction 'SDP-Plus (Frenz, 1985)' _computing_molecular_graphics 'ORTEPII (Jonhson, 1976)' _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'MULTAN11/82 (Main et al., 1982)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Enraf Nonius CAD-4' _diffrn_measurement_method 'profile data from \w-2\q' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0858 _diffrn_reflns_av_sigmaI/netI 0.0899 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 5148 _diffrn_reflns_theta_max 29.97 _diffrn_reflns_theta_min 3.01 _diffrn_standards_decay_% 2.7 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 10.337 _exptl_absorpt_correction_T_max 0.356 _exptl_absorpt_correction_T_min 0.237 _exptl_absorpt_correction_type '\y scan (North, Phillips & Mathews, 1968)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 2.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_description parallelepiped _exptl_crystal_F_000 528 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _refine_diff_density_max .479 _refine_diff_density_min -.920 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.013 _refine_ls_goodness_of_fit_obs 1.018 _refine_ls_hydrogen_treatment 'H atoms riding' _refine_ls_matrix_type full _refine_ls_number_parameters 101 _refine_ls_number_reflns 1800 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.013 _refine_ls_restrained_S_obs 1.018 _refine_ls_R_factor_all 0.1112 _refine_ls_R_factor_obs 0.0279 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w = 1/[\s^2^(Fo^2^)+(0.023P)^2^+0.4639P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_all 0.0681 _refine_ls_wR_factor_obs 0.0507 _reflns_number_observed 1031 _reflns_number_total 1800 _reflns_observed_criterion >2sigma(I) _[local]_cod_data_source_file na1276.cif _[local]_cod_data_source_block acs _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_database_code 2006078 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_occupancy _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_type_symbol Br1 1 0.77362(13) 0.69805(3) 0.30888(4) 0.0427(2) Uani d . Br Br2 1 0.69311(13) 0.36890(3) 0.41705(4) 0.0423(2) Uani d . Br O1 1 0.1178(11) 0.6344(2) 0.0098(3) 0.0598(10) Uani d . O O2 1 0.3008(9) 0.3601(2) 0.1920(3) 0.0434(8) Uani d . O H2 1 0.2075(140) 0.3577(7) 0.1286(21) 0.065 Uiso calc R H C1 1 0.4172(11) 0.5804(2) 0.1701(3) 0.0310(10) Uani d . C C2 1 0.6101(11) 0.5938(2) 0.2687(3) 0.0307(9) Uani d . C C3 1 0.6934(11) 0.5306(2) 0.3422(3) 0.0322(10) Uani d . C H3 1 0.8197(11) 0.5401(2) 0.4093(3) 0.048 Uiso calc R H C4 1 0.5862(11) 0.4534(2) 0.3143(3) 0.0309(10) Uani d . C C5 1 0.3963(11) 0.4374(2) 0.2144(4) 0.0312(9) Uani d . C C6 1 0.3164(12) 0.5015(3) 0.1434(4) 0.0339(10) Uani d . C H6 1 0.1920(12) 0.4919(3) 0.0759(4) 0.051 Uiso calc R H C7 1 0.3032(12) 0.6460(3) 0.0921(4) 0.0405(11) Uani d . C H7 1 0.3778(12) 0.7004(3) 0.0966(4) 0.061 Uiso d R H 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 . 1.895(4) yes Br2 C4 . 1.887(4) yes O1 C7 . 1.205(6) yes O2 C5 . 1.356(5) yes O2 H2 . 0.82 no C1 C2 . 1.380(6) no C1 C6 . 1.397(6) no C1 C7 . 1.479(6) yes C2 C3 . 1.389(6) no C3 C4 . 1.380(6) no C3 H3 . 0.93 no C4 C5 . 1.394(6) no C5 C6 . 1.380(6) no C6 H6 . 0.93 no C7 H7 . 0.95 no loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 Br1 0.0477(3) -0.0039(2) -0.0112(2) 0.0279(2) -0.0040(2) 0.0509(3) Br2 0.0556(3) 0.0057(2) -0.0081(2) 0.0340(2) 0.0037(2) 0.0361(2) O1 0.084(3) -0.009(2) -0.028(2) 0.046(2) 0.011(2) 0.046(2) O2 0.061(2) -0.0053(15) -0.013(2) 0.028(2) -0.0029(14) 0.040(2) C1 0.031(2) 0.001(2) 0.000(2) 0.030(2) 0.000(2) 0.032(2) C2 0.034(2) -0.003(2) 0.000(2) 0.024(2) -0.004(2) 0.034(2) C3 0.029(2) 0.002(2) -0.005(2) 0.037(2) -0.005(2) 0.030(2) C4 0.036(3) 0.008(2) 0.000(2) 0.032(2) 0.002(2) 0.025(2) C5 0.032(2) -0.001(2) 0.001(2) 0.029(2) -0.003(2) 0.033(2) C6 0.041(2) -0.004(2) -0.006(2) 0.031(2) -0.001(2) 0.029(2) C7 0.046(3) -0.003(2) -0.007(2) 0.033(2) 0.006(2) 0.041(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Br Br -.2901 2.4595 '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' 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' 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 C5 O2 H2 109.5(2) no C2 C1 C6 118.7(4) yes C2 C1 C7 123.2(4) yes C6 C1 C7 118.0(4) yes C1 C2 C3 120.8(4) yes C1 C2 Br1 121.7(3) yes C3 C2 Br1 117.5(3) yes C4 C3 C2 119.1(3) yes C4 C3 H3 120.4(2) no C2 C3 H3 120.4(2) no C3 C4 C5 121.7(4) yes C3 C4 Br2 118.4(3) yes C5 C4 Br2 119.9(3) yes O2 C5 C6 123.6(4) yes O2 C5 C4 118.6(4) yes C6 C5 C4 117.8(4) yes C5 C6 C1 121.8(4) yes C5 C6 H6 119.1(2) no C1 C6 H6 119.1(2) no O1 C7 C1 122.7(4) yes O1 C7 H7 111.9(3) no C1 C7 H7 125.2(2) 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 C6 C1 C2 C3 -2.1(7) no C7 C1 C2 C3 176.1(4) no C6 C1 C2 Br1 177.4(3) no C7 C1 C2 Br1 -4.3(6) no C1 C2 C3 C4 1.3(7) no Br1 C2 C3 C4 -178.3(3) no C2 C3 C4 C5 -0.1(7) no C2 C3 C4 Br2 -178.5(3) no C3 C4 C5 O2 179.7(4) no Br2 C4 C5 O2 -1.9(6) no C3 C4 C5 C6 -0.2(7) no Br2 C4 C5 C6 178.2(3) no O2 C5 C6 C1 179.4(5) no C4 C5 C6 C1 -0.7(7) no C2 C1 C6 C5 1.9(7) no C7 C1 C6 C5 -176.5(4) no C2 C1 C7 O1 -175.3(5) no C6 C1 C7 O1 3.0(8) no