#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/04/2200474.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_2200474 loop_ _publ_author_name 'Duclos, S\'everine' 'Therrien, Bruno' 'Ward, Thomas R.' _publ_section_title ; 5-Bromo-2-hydroxybenzene-1,3-dicarbaldehyde ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o884 _journal_page_last o885 _journal_paper_doi 10.1107/S1600536801013630 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C8 H5 Br O3' _chemical_formula_moiety 'C8 H5 Br O3' _chemical_formula_sum 'C8 H5 Br O3' _chemical_formula_weight 229.03 _chemical_name_systematic ; 5-bromo-2-hydroxybenzene-1,3-dicarbaldehyde ; _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-97 _cell_angle_alpha 90.00 _cell_angle_beta 96.84(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.5206(15) _cell_length_b 3.9367(8) _cell_length_c 25.881(5) _cell_measurement_reflns_used 3595 _cell_measurement_temperature 203(2) _cell_measurement_theta_max 26.78 _cell_measurement_theta_min 1.58 _cell_volume 760.8(3) _computing_cell_refinement 'SAINT (Siemens 1994-1996)' _computing_data_collection 'SMART (Siemens 1994-1996)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Siemens, 1996)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 203(2) _diffrn_measured_fraction_theta_full .000 _diffrn_measured_fraction_theta_max .917 _diffrn_measurement_device_type 'Siemens SMART CCD' _diffrn_measurement_method ; \w scans, 1271 frames, 0.30\%, 10 s, detector distance 5.5 cm, detector angle 23.0\% ; _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 .1075 _diffrn_reflns_av_sigmaI/netI .0804 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 3595 _diffrn_reflns_theta_full .50 _diffrn_reflns_theta_max 26.78 _diffrn_reflns_theta_min 1.58 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 5.359 _exptl_absorpt_correction_T_max .807 _exptl_absorpt_correction_T_min .528 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Blessing, 1995)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 2.000 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 448 _exptl_crystal_size_max .15 _exptl_crystal_size_mid .06 _exptl_crystal_size_min .04 _refine_diff_density_max .620 _refine_diff_density_min -.773 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 125 _refine_ls_number_reflns 1476 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.149 _refine_ls_R_factor_all .0532 _refine_ls_R_factor_gt .0449 _refine_ls_shift/su_max .021 _refine_ls_shift/su_mean .002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0504P)^2^+1.1160P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1223 _reflns_number_gt 1280 _reflns_number_total 1476 _reflns_threshold_expression I>2\s(I) _cod_data_source_file cv6044.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2200474 _cod_database_fobs_code 2200474 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 Br .22223(5) .23808(10) .015353(16) .0332(2) Uani d . 1 . . Br O4 .6948(4) -.1580(9) .20916(12) .0318(7) Uani d . 1 . . O H4 .627(9) -.282(13) .228(3) .040(6) Uiso d . 1 . . H O7 .9031(4) .4441(9) .10756(14) .0433(8) Uani d . 1 . . O O8 .4140(4) -.4438(8) .24075(12) .0352(7) Uani d . 1 . . O C1 .3673(5) .1103(10) .07678(16) .0254(8) Uani d . 1 . . C C2 .5444(6) .2136(10) .08367(18) .0262(9) Uani d . 1 . . C H2 .597(8) .342(13) .056(2) .040(6) Uiso d . 1 . . H C3 .6543(5) .1263(11) .12867(15) .0244(8) Uani d . 1 . . C C4 .5851(5) -.0690(10) .16694(14) .0231(8) Uani d . 1 . . C C5 .4035(5) -.1650(10) .15984(16) .0238(8) Uani d . 1 . . C C6 .2966(5) -.0769(10) .11430(16) .0249(8) Uani d . 1 . . C H6 .178(8) -.164(14) .112(2) .040(6) Uiso d . 1 . . H C7 .8420(6) .2418(11) .13658(19) .0302(10) Uani d . 1 . . C H7 .909(8) .151(13) .166(2) .040(6) Uiso d . 1 . . H C8 .3281(6) -.3607(11) .19971(16) .0267(8) Uani d . 1 . . C H8 .205(7) -.432(13) .192(2) .040(6) Uiso d . 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 Br .0287(3) .0403(3) .0275(3) -.00088(17) -.00899(19) .00215(17) O4 .0237(14) .0465(17) .0230(15) -.0047(14) -.0067(12) .0032(14) O7 .0262(15) .054(2) .049(2) -.0078(15) .0019(14) .0066(17) O8 .0300(15) .0456(19) .0296(16) -.0030(14) .0017(12) .0026(14) C1 .0211(19) .026(2) .027(2) .0020(16) -.0032(15) -.0027(17) C2 .0214(19) .029(2) .029(2) -.0001(16) .0022(16) -.0035(17) C3 .0196(18) .0301(19) .023(2) -.0011(16) -.0006(14) -.0065(17) C4 .0191(17) .029(2) .0202(18) .0041(15) -.0034(14) -.0060(16) C5 .0232(19) .0253(19) .023(2) -.0019(15) .0023(16) -.0049(16) C6 .0151(18) .029(2) .029(2) .0020(15) -.0036(15) -.0046(17) C7 .0180(19) .042(3) .031(2) .0002(17) .0029(17) .0015(19) C8 .0222(19) .032(2) .025(2) -.0014(17) .0015(16) -.0050(18) 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' O O .0106 .0060 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C4 O4 H4 105(4) C6 C1 C2 120.9(4) C6 C1 Br 120.3(3) C2 C1 Br 118.8(3) C1 C2 C3 120.2(4) C1 C2 H2 121(3) C3 C2 H2 119(3) C2 C3 C4 119.7(4) C2 C3 C7 120.3(4) C4 C3 C7 120.0(4) O4 C4 C3 118.5(3) O4 C4 C5 122.1(4) C3 C4 C5 119.4(3) C6 C5 C4 119.9(4) C6 C5 C8 119.9(4) C4 C5 C8 120.2(4) C1 C6 C5 120.0(4) C1 C6 H6 126(3) C5 C6 H6 114(3) O7 C7 C3 122.7(4) O7 C7 H7 123(3) C3 C7 H7 114(3) O8 C8 C5 123.3(4) O8 C8 H8 120(3) C5 C8 H8 116(3) 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 Br C1 . 1.886(4) ? O4 C4 . 1.335(5) ? O4 H4 . .89(6) ? O7 C7 . 1.221(6) ? O8 C8 . 1.220(5) ? C1 C6 . 1.376(6) ? C1 C2 . 1.384(6) ? C2 C3 . 1.388(6) ? C2 H2 . 1.00(6) ? C3 C4 . 1.402(6) ? C3 C7 . 1.474(6) ? C4 C5 . 1.408(5) ? C5 C6 . 1.389(6) ? C5 C8 . 1.456(6) ? C6 H6 . .95(6) ? C7 H7 . .94(6) ? C8 H8 . .96(5) ? 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 _geom_hbond_publ_flag O4 H4 O8 . .891 1.791 2.608(7) 151.47 yes O4 H4 O4 2_645 .891 2.474 2.935(7) 112.69 yes C2 H2 Br 3_665 1.001 2.927 3.921(5) 172.68 yes C6 H6 O7 1_445 .954 2.569 3.495(9) 164.28 yes C7 H7 O4 . .941 2.395 2.779(8) 104.17 yes 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 C6 C1 C2 C3 .6(6) Br C1 C2 C3 179.4(3) C1 C2 C3 C4 .4(6) C1 C2 C3 C7 -178.8(4) C2 C3 C4 O4 178.1(4) C7 C3 C4 O4 -2.7(6) C2 C3 C4 C5 -1.9(6) C7 C3 C4 C5 177.3(4) O4 C4 C5 C6 -177.6(4) C3 C4 C5 C6 2.5(6) O4 C4 C5 C8 1.5(6) C3 C4 C5 C8 -178.5(4) C2 C1 C6 C5 -.1(6) Br C1 C6 C5 -178.9(3) C4 C5 C6 C1 -1.5(6) C8 C5 C6 C1 179.5(4) C2 C3 C7 O7 7.9(7) C4 C3 C7 O7 -171.3(4) C6 C5 C8 O8 -179.3(4) C4 C5 C8 O8 1.6(6) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 4425351 2 PubChem 5260206