# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'A. Nangia' _publ_contact_author_address ; School of Chemistry University of Hyderabad P O Central University Hyderabad 500046 Hyderabad INDIA ; _publ_contact_author_email 'ASHWINI NANGIA@REDIFFMAIL.COM' _publ_section_title ; First example of ice-like boat water hexamer tape structure in a supramolecular organic host ; loop_ _publ_author_name 'A. Nangia' 'Binoy K. Saha' # Attachment 'dbpg-100.cif' data_dbpg-100 _database_code_depnum_ccdc_archive 'CCDC 294904' _audit_creation_method SHELXL-97 _chemical_name_systematic ; dibromophloroglucinol, tetrahydrate ; _chemical_name_common 'dibromophloroglucinol, tetrahydrate' _chemical_melting_point ? _chemical_formula_moiety 'C6 H4 Br2 O3, 4(H2 O)' _chemical_formula_sum 'C6 H12 Br2 O7' _chemical_formula_weight 355.98 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.0309(12) _cell_length_b 10.6848(8) _cell_length_c 7.3246(5) _cell_angle_alpha 90.00 _cell_angle_beta 111.4500(10) _cell_angle_gamma 90.00 _cell_volume 1167.71(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2290 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 28.07 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.025 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 6.955 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2074 _exptl_absorpt_correction_T_max 0.4891 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3137 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0203 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 26.01 _reflns_number_total 1151 _reflns_number_gt 1071 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. H1 of O1 is disordered due to symmetry in two places and one H of O4 is disordered over two places (H4b and H4c) with occupancy 0.5 each. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0287P)^2^+1.0391P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1151 _refine_ls_number_parameters 98 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0218 _refine_ls_R_factor_gt 0.0198 _refine_ls_wR_factor_ref 0.0502 _refine_ls_wR_factor_gt 0.0493 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.179174(13) 0.366096(19) 1.02104(3) 0.01641(10) Uani 1 1 d . . . O1 O 0.0000 0.2615(2) 0.7500 0.0206(5) Uani 1 2 d S . . H1 H 0.024(3) 0.228(5) 0.825(7) 0.012(13) Uiso 0.50 1 d P . . O2 O 0.14984(11) 0.64388(15) 0.9896(2) 0.0151(3) Uani 1 1 d . . . H2 H 0.150(2) 0.713(3) 0.965(4) 0.030(8) Uiso 1 1 d . . . C1 C 0.0000 0.3881(3) 0.7500 0.0136(6) Uani 1 2 d S . . C2 C 0.07534(13) 0.4542(2) 0.8676(3) 0.0127(4) Uani 1 1 d . . . C3 C 0.07535(13) 0.5844(2) 0.8699(3) 0.0131(4) Uani 1 1 d . . . C4 C 0.0000 0.6495(3) 0.7500 0.0123(6) Uani 1 2 d S . . H4 H 0.0000 0.7365 0.7500 0.015 Uiso 1 2 calc SR . . O3 O 0.16424(13) 0.88365(16) 0.9033(3) 0.0194(4) Uani 1 1 d . . . H3A H 0.208(2) 0.888(2) 0.931(4) 0.013(8) Uiso 1 1 d . . . H3B H 0.143(3) 0.948(4) 0.944(6) 0.072(12) Uiso 1 1 d . . . O4 O 0.07508(13) 0.93092(18) 0.5121(3) 0.0206(4) Uani 1 1 d . . . H4A H 0.106(3) 0.924(4) 0.616(6) 0.063(13) Uiso 1 1 d . . . H4B H 0.025(4) 0.977(6) 0.486(9) 0.029(15) Uiso 0.50 1 d P . . H4C H 0.069(5) 0.887(6) 0.451(10) 0.02(2) Uiso 0.50 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.01104(14) 0.01266(14) 0.02255(15) 0.00169(8) 0.00263(10) 0.00194(7) O1 0.0229(13) 0.0090(12) 0.0221(14) 0.000 -0.0011(11) 0.000 O2 0.0095(7) 0.0110(8) 0.0212(8) -0.0009(6) 0.0013(6) -0.0019(6) C1 0.0144(14) 0.0098(14) 0.0181(15) 0.000 0.0078(12) 0.000 C2 0.0090(9) 0.0131(10) 0.0153(10) 0.0020(8) 0.0035(8) 0.0038(8) C3 0.0096(10) 0.0152(11) 0.0162(10) -0.0015(8) 0.0068(8) -0.0019(8) C4 0.0096(14) 0.0077(14) 0.0198(15) 0.000 0.0055(12) 0.000 O3 0.0091(9) 0.0141(9) 0.0319(10) -0.0013(7) 0.0038(7) -0.0015(7) O4 0.0182(9) 0.0157(10) 0.0244(10) -0.0004(9) 0.0036(8) 0.0011(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C2 1.8846(19) . ? O1 C1 1.353(4) . ? O1 H1 0.65(5) . ? O2 C3 1.354(3) . ? O2 H2 0.76(3) . ? C1 C2 1.392(3) 2_556 ? C1 C2 1.392(3) . ? C2 C3 1.391(3) . ? C3 C4 1.392(2) . ? C4 C3 1.392(2) 2_556 ? C4 H4 0.9300 . ? O3 H3A 0.66(3) . ? O3 H3B 0.87(4) . ? O4 H4A 0.74(4) . ? O4 H4B 0.90(5) . ? O4 H4C 0.63(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 123(5) . . ? C3 O2 H2 112(2) . . ? O1 C1 C2 120.48(13) . 2_556 ? O1 C1 C2 120.47(13) . . ? C2 C1 C2 119.0(3) 2_556 . ? C3 C2 C1 120.72(19) . . ? C3 C2 Br1 119.74(15) . . ? C1 C2 Br1 119.53(17) . . ? O2 C3 C2 118.25(18) . . ? O2 C3 C4 122.0(2) . . ? C2 C3 C4 119.72(19) . . ? C3 C4 C3 120.1(3) 2_556 . ? C3 C4 H4 120.0 2_556 . ? C3 C4 H4 120.0 . . ? H3A O3 H3B 111(3) . . ? H4A O4 H4B 119(5) . . ? H4A O4 H4C 121(7) . . ? H4B O4 H4C 111(7) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.471 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.094 # Attachment 'dbpg-rt1.cif' data_dbpg-rt1 _database_code_depnum_ccdc_archive 'CCDC 294905' _audit_creation_method SHELXL-97 _chemical_name_systematic ; dibromophloroglucinol, tetrahydrate ; _chemical_name_common 'dibromophloroglucinol, tetrahydrate' _chemical_melting_point ? _chemical_formula_moiety 'C6 H4 Br2 O3, 4(H2 O)' _chemical_formula_sum 'C6 H12 Br2 O7' _chemical_formula_weight 355.98 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.135(4) _cell_length_b 10.740(2) _cell_length_c 7.4390(17) _cell_angle_alpha 90.00 _cell_angle_beta 111.354(3) _cell_angle_gamma 90.00 _cell_volume 1200.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2727 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 27.72 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.970 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 6.765 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1239 _exptl_absorpt_correction_T_max 0.4734 _exptl_absorpt_process_details 'Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5188 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 25.50 _reflns_number_total 1117 _reflns_number_gt 992 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The seven restraints are due to the fixing of seven O-H distances at 0.82 A in water as well as phenol and four restraints are due to fixing four HOH angle at 105 degree of water molecules. H1 of O1 is disordered due to symmetry in two places and one H of O4 is disordered over two places (H4b and H4c) with occupeancy 0.5 each. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0384P)^2^+0.8381P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1117 _refine_ls_number_parameters 98 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.0301 _refine_ls_R_factor_gt 0.0253 _refine_ls_wR_factor_ref 0.0667 _refine_ls_wR_factor_gt 0.0632 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.178049(19) 0.36720(2) 1.01279(4) 0.04616(15) Uani 1 1 d . . . O1 O 0.0000 0.2631(2) 0.7500 0.0487(7) Uani 1 2 d SD . . H1 H 0.028(4) 0.233(6) 0.855(5) 0.06(2) Uiso 0.50 1 d PD . . O2 O 0.14911(15) 0.64330(16) 0.9812(3) 0.0417(5) Uani 1 1 d D . . H2 H 0.146(3) 0.7158(14) 0.947(5) 0.069(11) Uiso 1 1 d D . . C1 C 0.0000 0.3897(3) 0.7500 0.0339(8) Uani 1 2 d S . . C2 C 0.07474(16) 0.4545(2) 0.8637(4) 0.0330(5) Uani 1 1 d . . . C3 C 0.07496(16) 0.5836(2) 0.8654(4) 0.0318(5) Uani 1 1 d . . . C4 C 0.0000 0.6481(3) 0.7500 0.0348(8) Uani 1 2 d S . . H4 H 0.0000 0.7347 0.7500 0.042 Uiso 1 2 calc SR . . O3 O 0.16414(16) 0.88345(19) 0.8979(4) 0.0535(6) Uani 1 1 d D . . H3A H 0.2167(9) 0.894(3) 0.920(5) 0.066(12) Uiso 1 1 d D . . H3B H 0.149(2) 0.942(3) 0.951(6) 0.105(17) Uiso 1 1 d D . . O4 O 0.07524(17) 0.9315(2) 0.5089(4) 0.0555(6) Uani 1 1 d D . . H4A H 0.109(2) 0.935(5) 0.621(3) 0.12(2) Uiso 1 1 d D . . H4B H 0.032(2) 0.972(5) 0.502(7) 0.039(17) Uiso 0.50 1 d PD . . H4C H 0.057(4) 0.860(2) 0.495(9) 0.17(6) Uiso 0.50 1 d PD . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0299(2) 0.0340(2) 0.0640(2) 0.00495(11) 0.00461(14) 0.00593(10) O1 0.0473(19) 0.0216(14) 0.061(2) 0.000 0.0000(16) 0.000 O2 0.0270(10) 0.0292(10) 0.0576(12) -0.0018(8) 0.0021(9) -0.0041(8) C1 0.032(2) 0.0220(17) 0.047(2) 0.000 0.0138(16) 0.000 C2 0.0226(13) 0.0286(12) 0.0444(14) 0.0023(10) 0.0083(11) 0.0044(10) C3 0.0242(13) 0.0286(13) 0.0419(13) -0.0017(10) 0.0110(11) -0.0011(10) C4 0.026(2) 0.0245(17) 0.050(2) 0.000 0.0099(16) 0.000 O3 0.0311(13) 0.0343(12) 0.0840(17) -0.0028(10) 0.0079(11) -0.0035(9) O4 0.0484(14) 0.0381(13) 0.0707(16) -0.0038(10) 0.0106(12) 0.0014(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C2 1.882(2) . ? O1 C1 1.360(4) . ? O1 H1 0.814(10) . ? O2 C3 1.354(3) . ? O2 H2 0.815(10) . ? C1 C2 1.382(3) . ? C1 C2 1.382(3) 2_556 ? C2 C3 1.387(4) . ? C3 C4 1.387(3) . ? C4 C3 1.387(3) 2_556 ? C4 H4 0.9300 . ? O3 H3A 0.811(10) . ? O3 H3B 0.819(10) . ? O4 H4A 0.812(10) . ? O4 H4B 0.815(10) . ? O4 H4C 0.818(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 114(5) . . ? C3 O2 H2 108(3) . . ? O1 C1 C2 120.22(16) . . ? O1 C1 C2 120.22(16) . 2_556 ? C2 C1 C2 119.6(3) . 2_556 ? C1 C2 C3 120.5(2) . . ? C1 C2 Br1 119.9(2) . . ? C3 C2 Br1 119.61(19) . . ? O2 C3 C2 118.5(2) . . ? O2 C3 C4 121.8(2) . . ? C2 C3 C4 119.7(2) . . ? C3 C4 C3 120.1(3) 2_556 . ? C3 C4 H4 120.0 2_556 . ? C3 C4 H4 120.0 . . ? H3A O3 H3B 105.3(16) . . ? H4A O4 H4B 105.7(17) . . ? H4A O4 H4C 104.4(17) . . ? H4B O4 H4C 104.1(18) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.313 _refine_diff_density_min -0.518 _refine_diff_density_rms 0.116 # Attachment 'dbpg-anh.cif' data_an344m _database_code_depnum_ccdc_archive 'CCDC 294906' _audit_creation_method SHELXL-97 _chemical_name_systematic ; dibromophloroglucinol ; _chemical_name_common dibromophloroglucinol _chemical_melting_point ? _chemical_formula_moiety 'C6 H4 Br2 O3' _chemical_formula_sum 'C6 H4 Br2 O3' _chemical_formula_weight 283.91 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 5.4011(5) _cell_length_b 12.8974(13) _cell_length_c 10.9478(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 762.63(13) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2154 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 25.86 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.473 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 10.579 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1946 _exptl_absorpt_correction_T_max 0.2518 _exptl_absorpt_process_details 'Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3093 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 25.89 _reflns_number_total 741 _reflns_number_gt 664 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Three restraints are due to the fixing of three O-H distances at 0.82 A. H1 of O1 is disordered over two places for symmetry and H of O2 is also disoredred over two places with 0.5 occupancy each. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0346P)^2^+2.4325P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0105(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 741 _refine_ls_number_parameters 65 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0794 _refine_ls_wR_factor_gt 0.0771 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.113 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.10193(8) 0.20004(3) 0.58217(4) 0.0317(2) Uani 1 1 d . . . O1 O 0.5000 0.2872(3) 0.7500 0.0322(10) Uani 1 2 d SD . . H1 H 0.429(13) 0.312(6) 0.693(5) 0.01(2) Uiso 0.50 1 d PD . . O2 O 0.1659(8) -0.0334(3) 0.6100(4) 0.0499(10) Uani 1 1 d D . . H2A H 0.12(2) -0.006(11) 0.547(7) 0.07(5) Uiso 0.50 1 d PD . . H2B H 0.145(16) -0.095(2) 0.622(8) 0.02(2) Uiso 0.50 1 d PD . . C1 C 0.5000 0.1816(4) 0.7500 0.0226(11) Uani 1 2 d S . . C2 C 0.3342(7) 0.1272(3) 0.6782(4) 0.0244(8) Uani 1 1 d . . . C3 C 0.3332(9) 0.0206(3) 0.6774(4) 0.0318(10) Uani 1 1 d . . . C4 C 0.5000 -0.0328(5) 0.7500 0.0405(16) Uani 1 2 d S . . H4 H 0.5000 -0.1049 0.7500 0.049 Uiso 1 2 calc SR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0317(3) 0.0281(3) 0.0352(3) 0.00351(17) -0.00797(17) 0.00027(16) O1 0.049(3) 0.015(2) 0.033(2) 0.000 -0.011(2) 0.000 O2 0.065(2) 0.028(2) 0.057(2) 0.0046(18) -0.032(2) -0.0182(18) C1 0.023(3) 0.017(3) 0.027(3) 0.000 0.002(2) 0.000 C2 0.0248(18) 0.022(2) 0.0262(19) 0.0043(16) -0.0035(16) 0.0009(16) C3 0.036(2) 0.021(2) 0.038(2) -0.0014(18) -0.0080(19) -0.0052(18) C4 0.052(4) 0.018(3) 0.051(4) 0.000 -0.023(3) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C2 1.887(4) . ? O1 C1 1.362(7) . ? O1 H1 0.80(2) . ? O2 C3 1.359(5) . ? O2 H2A 0.81(2) . ? O2 H2B 0.81(2) . ? C1 C2 1.383(5) 3_656 ? C1 C2 1.383(5) . ? C2 C3 1.375(6) . ? C3 C4 1.385(5) . ? C4 C3 1.385(5) 3_656 ? C4 H4 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 114(6) . . ? C3 O2 H2A 116(10) . . ? C3 O2 H2B 120(6) . . ? H2A O2 H2B 121(10) . . ? O1 C1 C2 120.5(3) . 3_656 ? O1 C1 C2 120.5(3) . . ? C2 C1 C2 119.0(5) 3_656 . ? C3 C2 C1 120.9(4) . . ? C3 C2 Br1 119.5(3) . . ? C1 C2 Br1 119.6(3) . . ? O2 C3 C2 121.2(4) . . ? O2 C3 C4 119.3(4) . . ? C2 C3 C4 119.4(4) . . ? C3 C4 C3 120.4(6) . 3_656 ? C3 C4 H4 119.8 . . ? C3 C4 H4 119.8 3_656 . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.89 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.642 _refine_diff_density_min -0.523 _refine_diff_density_rms 0.106