data_2203186 loop_ _publ_author_name 'Kirsop, Peter' 'Storey, John M. D.' 'Harrison, William T. A.' _publ_section_title ; 1,3,5-Tribromo-2,6-dihydroxybenzene ; _journal_issue 2 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o222 _journal_page_last o224 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C6 H3 Br3 O2' _chemical_formula_moiety 'C6 H3 Br3 O2' _chemical_formula_sum 'C6 H3 Br3 O2' _chemical_formula_weight 346.81 _chemical_melting_point 280 _chemical_name_common tribromoresorcinol _chemical_name_systematic ; ; _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens 'difmap (O-H) and geom (C-H)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.1071(3) _cell_length_b 12.8550(10) _cell_length_c 15.2960(10) _cell_measurement_reflns_used 12216 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.91 _cell_volume 807.60(10) _computing_cell_refinement 'HKL SCALEPACK (Otwinowski & Minor 1997)' _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_data_reduction 'HKL DENZO and SCALEPACK (Otwinowski & Minor 1997) and SORTAV (Blessing, 1995)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Enraf-Nonius KappaCCD' _diffrn_measurement_method '\w and \f' _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 0.0659 _diffrn_reflns_av_sigmaI/netI 0.0797 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 7322 _diffrn_reflns_theta_full 27.44 _diffrn_reflns_theta_max 27.44 _diffrn_reflns_theta_min 3.10 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _exptl_absorpt_coefficient_mu 14.927 _exptl_absorpt_correction_T_max 0.636 _exptl_absorpt_correction_T_min 0.067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 2.853 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 640 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.725 _refine_diff_density_min -0.625 _refine_ls_abs_structure_details 'Flack H D (1983), 727 Friedel pairs' _refine_ls_abs_structure_Flack 0.04(3) _refine_ls_extinction_coef 0.0021(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 107 _refine_ls_number_reflns 1820 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.997 _refine_ls_R_factor_all 0.0658 _refine_ls_R_factor_gt 0.0375 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0143P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.0564 _reflns_number_gt 1390 _reflns_number_total 1820 _reflns_threshold_expression I>2\s(I) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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 C1 0.7209(15) -0.0499(4) 0.4241(4) 0.0172(14) Uani d . 1 . . C C2 0.6566(14) 0.0039(4) 0.3483(4) 0.0167(15) Uani d . 1 . . C C3 0.4764(15) 0.0959(4) 0.3527(4) 0.0172(15) Uani d . 1 . . C C4 0.3643(14) 0.1321(5) 0.4326(4) 0.0192(14) Uani d . 1 . . C H4 0.2428 0.1949 0.4357 0.023 Uiso calc R 1 . . H C5 0.4303(15) 0.0766(4) 0.5075(4) 0.0148(14) Uani d . 1 . . C C6 0.6087(15) -0.0159(4) 0.5058(4) 0.0176(14) Uani d . 1 . . C O1 0.7570(11) -0.0285(3) 0.2683(3) 0.0237(11) Uani d . 1 . . O H1 0.849(14) -0.085(4) 0.270(4) 0.028 Uiso d . 1 . . H O2 0.6795(11) -0.0752(3) 0.5767(3) 0.0219(12) Uani d . 1 . . O H2 0.634(16) -0.043(5) 0.617(4) 0.026 Uiso d . 1 . . H Br1 0.95355(16) -0.17647(5) 0.41737(4) 0.02168(17) Uani d . 1 . . Br Br2 0.38328(13) 0.17109(5) 0.24986(4) 0.02274(18) Uani d . 1 . . Br Br3 0.26244(16) 0.12500(5) 0.61575(4) 0.02241(18) Uani d . 1 . . Br 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 C1 0.022(3) 0.012(3) 0.018(4) 0.004(3) -0.003(3) -0.003(3) C2 0.017(4) 0.021(3) 0.013(4) -0.008(3) 0.002(3) -0.003(3) C3 0.019(3) 0.017(3) 0.015(4) 0.001(3) -0.006(3) 0.003(3) C4 0.021(4) 0.015(3) 0.022(4) -0.001(3) -0.006(3) 0.001(3) C5 0.017(3) 0.019(3) 0.008(3) -0.002(3) 0.003(3) -0.002(3) C6 0.024(3) 0.016(3) 0.013(4) -0.006(3) -0.006(3) 0.005(3) O1 0.033(2) 0.020(2) 0.018(3) 0.004(2) 0.005(2) -0.003(2) O2 0.031(3) 0.020(2) 0.015(3) 0.000(2) 0.001(2) 0.0017(19) Br1 0.0239(3) 0.0182(3) 0.0230(4) 0.0023(3) -0.0018(3) -0.0014(3) Br2 0.0281(3) 0.0229(3) 0.0173(4) 0.0016(3) -0.0019(3) 0.0025(3) Br3 0.0245(3) 0.0252(3) 0.0175(3) 0.0024(3) 0.0016(3) -0.0007(3) 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' 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 C1 C6 . . 122.1(5) ? C2 C1 Br1 . . 119.0(5) ? C6 C1 Br1 . . 118.9(4) ? O1 C2 C1 . . 123.2(5) ? O1 C2 C3 . . 117.7(5) ? C1 C2 C3 . . 119.2(5) ? C4 C3 C2 . . 120.2(5) ? C4 C3 Br2 . . 119.7(4) ? C2 C3 Br2 . . 120.1(5) ? C5 C4 C3 . . 119.6(5) ? C5 C4 H4 . . 120.2 ? C3 C4 H4 . . 120.2 ? C4 C5 C6 . . 121.9(5) ? C4 C5 Br3 . . 118.9(5) ? C6 C5 Br3 . . 119.1(4) ? O2 C6 C5 . . 125.1(5) ? O2 C6 C1 . . 117.9(5) ? C5 C6 C1 . . 117.1(5) ? C2 O1 H1 . . 112(5) ? C6 O2 H2 . . 107(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 C1 C2 . 1.376(8) ? C1 C6 . 1.401(8) ? C1 Br1 . 1.890(5) ? C2 O1 . 1.358(7) ? C2 C3 . 1.396(7) ? C3 C4 . 1.387(8) ? C3 Br2 . 1.886(6) ? C4 C5 . 1.377(8) ? C4 H4 . 0.9500 ? C5 C6 . 1.397(8) ? C5 Br3 . 1.898(6) ? C6 O2 . 1.358(7) ? O1 H1 . 0.82(5) ? O2 H2 . 0.77(6) ? 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 O1 H1 Br1 . 0.82(5) 2.57(6) 3.078(4) 121(5) yes O1 H1 Br3 2_654 0.82(5) 2.90(6) 3.298(4) 112(5) yes O2 H2 O1 2_655 0.77(6) 2.52(6) 3.229(6) 153(6) yes O2 H2 Br3 . 0.77(6) 2.64(6) 3.148(4) 125(6) yes