# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Prof A Nangia' _publ_contact_author_address ; School of Chemistry University of Hyderabad P O Central University Hyderabad 500 046 INDIA ; _publ_contact_author_email 'ASHWINI NANGIA@REDIFFMAIL.COM' _publ_section_title ; Helical water chains in aquapores of organic hexahost: remarkable halogen-substitution effect on the handedness of water helix ; loop_ _publ_author_name 'A. Nangia' 'Binoy K. Saha' data_an183_m _database_code_depnum_ccdc_archive 'CCDC 257771' _audit_creation_method SHELXL-97 _chemical_name_systematic ; tribromophloroglucinol, trihydrate ; _chemical_name_common 'tribromophloroglucinol, trihydrate' _chemical_melting_point ? _chemical_formula_moiety 'C6 H3 Br3 O3, 3(H2 O)' _chemical_formula_sum 'C6 H9 Br3 O6' _chemical_formula_weight 416.86 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 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.1076(5) _cell_length_b 9.1708(7) _cell_length_c 16.7599(12) _cell_angle_alpha 90.00 _cell_angle_beta 93.9930(10) _cell_angle_gamma 90.00 _cell_volume 1089.80(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6031 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 28.19 _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.541 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 11.110 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1409 _exptl_absorpt_correction_T_max 0.1757 _exptl_absorpt_process_details '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 8509 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0192 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2218 _reflns_number_gt 2083 _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. ; _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^)+(0.0244P)^2^+1.1952P] 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 2218 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0213 _refine_ls_R_factor_gt 0.0193 _refine_ls_wR_factor_ref 0.0490 _refine_ls_wR_factor_gt 0.0483 _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_restrained_S_all 1.127 _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 0.60342(4) 0.16886(3) 0.486294(14) 0.01022(8) Uani 1 1 d . . . Br3 Br 0.75550(4) 0.69830(3) 0.330155(14) 0.01090(8) Uani 1 1 d . . . C1 C 0.6888(3) 0.4447(3) 0.42037(14) 0.0070(5) Uani 1 1 d . . . C6 C 0.7533(3) 0.5877(3) 0.42442(13) 0.0072(5) Uani 1 1 d . . . C2 C 0.6842(3) 0.3645(3) 0.49061(15) 0.0073(5) Uani 1 1 d . . . O1 O 0.6259(3) 0.3816(2) 0.35042(11) 0.0100(4) Uani 1 1 d . . . O4 O 0.3019(3) 0.5954(3) 0.20790(13) 0.0177(4) Uani 1 1 d . . . O5 O -0.0259(3) 0.5138(2) 0.11337(13) 0.0145(4) Uani 1 1 d . . . C5 C 0.8169(3) 0.6515(3) 0.49716(15) 0.0075(5) Uani 1 1 d . . . C3 C 0.7393(3) 0.4264(3) 0.56442(14) 0.0075(5) Uani 1 1 d . . . C4 C 0.8071(3) 0.5690(3) 0.56651(14) 0.0074(5) Uani 1 1 d . . . O2 O 0.7289(3) 0.3452(2) 0.63137(11) 0.0112(4) Uani 1 1 d . . . O3 O 0.8838(3) 0.78884(19) 0.49543(11) 0.0100(4) Uani 1 1 d . . . Br2 Br 0.89210(4) 0.65026(3) 0.665817(14) 0.01111(8) Uani 1 1 d . . . O6 O 0.6433(4) 0.4405(3) 0.19067(14) 0.0186(5) Uani 1 1 d . . . H3 H 0.908(5) 0.820(4) 0.538(2) 0.027(10) Uiso 1 1 d . . . H2 H 0.741(6) 0.396(5) 0.663(2) 0.034(12) Uiso 1 1 d . . . H1 H 0.635(6) 0.420(5) 0.314(2) 0.039(13) Uiso 1 1 d . . . H5A H -0.015(5) 0.457(4) 0.090(2) 0.024(12) Uiso 1 1 d . . . H4B H 0.321(6) 0.661(5) 0.191(2) 0.028(12) Uiso 1 1 d . . . H6A H 0.639(7) 0.388(5) 0.174(3) 0.028(15) Uiso 1 1 d . . . H4A H 0.384(5) 0.555(4) 0.197(2) 0.018(10) Uiso 1 1 d . . . H6B H 0.736(6) 0.476(4) 0.172(2) 0.030(11) Uiso 1 1 d . . . H5B H 0.062(6) 0.528(4) 0.143(3) 0.034(11) Uiso 1 1 d . . . 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 0.01613(14) 0.00561(13) 0.00918(13) -0.00026(9) 0.00269(9) -0.00281(9) Br3 0.01683(14) 0.00870(14) 0.00719(13) 0.00217(9) 0.00085(9) -0.00281(9) C1 0.0060(11) 0.0079(12) 0.0074(11) -0.0020(9) 0.0023(9) 0.0011(9) C6 0.0085(12) 0.0083(12) 0.0052(11) 0.0029(9) 0.0033(9) -0.0004(9) C2 0.0101(12) 0.0021(11) 0.0100(12) -0.0004(9) 0.0032(9) -0.0019(9) O1 0.0164(10) 0.0088(9) 0.0047(9) -0.0007(7) 0.0010(7) -0.0029(7) O4 0.0213(12) 0.0117(12) 0.0194(11) -0.0015(9) -0.0033(9) 0.0018(10) O5 0.0204(11) 0.0094(10) 0.0135(10) -0.0043(8) -0.0015(8) 0.0018(8) C5 0.0062(12) 0.0052(12) 0.0114(12) -0.0005(9) 0.0032(9) 0.0000(9) C3 0.0071(11) 0.0088(12) 0.0067(11) 0.0016(9) 0.0025(9) 0.0011(9) C4 0.0095(12) 0.0072(12) 0.0058(11) -0.0030(9) 0.0010(9) -0.0012(9) O2 0.0206(10) 0.0086(9) 0.0046(9) 0.0010(7) 0.0022(7) -0.0034(7) O3 0.0174(10) 0.0060(9) 0.0066(9) -0.0013(7) 0.0021(7) -0.0039(7) Br2 0.01691(14) 0.01004(14) 0.00652(13) -0.00212(9) 0.00177(9) -0.00334(9) O6 0.0250(13) 0.0116(12) 0.0191(11) 0.0006(10) 0.0012(9) -0.0041(9) _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 1.884(2) . ? Br3 C6 1.879(2) . ? C1 O1 1.355(3) . ? C1 C6 1.389(3) . ? C1 C2 1.390(3) . ? C6 C5 1.399(3) . ? C2 C3 1.392(3) . ? O1 H1 0.71(4) . ? O4 H4B 0.68(4) . ? O4 H4A 0.73(4) . ? O5 H5A 0.65(4) . ? O5 H5B 0.78(4) . ? C5 O3 1.348(3) . ? C5 C4 1.393(3) . ? C3 O2 1.353(3) . ? C3 C4 1.393(3) . ? C4 Br2 1.884(2) . ? O2 H2 0.70(4) . ? O3 H3 0.78(4) . ? O6 H6A 0.55(4) . ? O6 H6B 0.81(4) . ? 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 O1 C1 C6 122.2(2) . . ? O1 C1 C2 118.8(2) . . ? C6 C1 C2 119.0(2) . . ? C1 C6 C5 121.5(2) . . ? C1 C6 Br3 119.39(18) . . ? C5 C6 Br3 119.08(18) . . ? C1 C2 C3 121.0(2) . . ? C1 C2 Br1 119.75(18) . . ? C3 C2 Br1 119.25(18) . . ? C1 O1 H1 119(4) . . ? H4B O4 H4A 99(4) . . ? H5A O5 H5B 113(4) . . ? O3 C5 C4 124.3(2) . . ? O3 C5 C6 117.7(2) . . ? C4 C5 C6 117.9(2) . . ? O2 C3 C2 119.0(2) . . ? O2 C3 C4 122.3(2) . . ? C2 C3 C4 118.7(2) . . ? C5 C4 C3 121.7(2) . . ? C5 C4 Br2 119.39(18) . . ? C3 C4 Br2 118.85(18) . . ? C3 O2 H2 104(3) . . ? C5 O3 H3 112(3) . . ? H6A O6 H6B 100(5) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.470 _refine_diff_density_min -0.840 _refine_diff_density_rms 0.155 data_an119_m _database_code_depnum_ccdc_archive 'CCDC 257772' _audit_creation_method SHELXL-97 _chemical_name_systematic ; trichlorophloroglucinol, trihydrate ; _chemical_name_common 'trichlorophloroglucinol, trihydrate' _chemical_melting_point ? _chemical_formula_moiety 'C6 H3 Cl3 O3, 3(H2 O)' _chemical_formula_sum 'C6 H9 Cl3 O6' _chemical_formula_weight 283.48 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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' _cell_length_a 6.9261(10) _cell_length_b 16.057(2) _cell_length_c 9.9510(15) _cell_angle_alpha 90.00 _cell_angle_beta 109.923(2) _cell_angle_gamma 90.00 _cell_volume 1040.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3319 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 28.21 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.810 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.886 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7239 _exptl_absorpt_correction_T_max 0.9406 _exptl_absorpt_process_details '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 8941 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 25.50 _reflns_number_total 1926 _reflns_number_gt 1769 _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 phenolic OH groups and water molecules are disordered.The hydrogens have beenrefined isotropically with occupancies H1A 0.73, H1B 0.23, H 2A 0.60, H2B 0.40, H3A 0.60, H 3B 0.40, H4A 1.0, H4B 0.73, H4C 0.23, H5A 1.0, H5B 0.60, H5C 0.40, H6A 1.0, H6B 0.60 and H6C 0.40. ; _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^)+(0.0397P)^2^+0.4083P] 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 1926 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0329 _refine_ls_R_factor_gt 0.0289 _refine_ls_wR_factor_ref 0.0725 _refine_ls_wR_factor_gt 0.0698 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 1.094 _refine_ls_shift/su_mean 0.006 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 Cl2 Cl 0.78587(7) 0.65285(3) 0.34999(5) 0.01643(15) Uani 1 1 d . . . Cl3 Cl 0.63331(8) 0.32224(3) 0.32674(5) 0.01924(15) Uani 1 1 d . . . Cl1 Cl 0.83285(8) 0.48510(3) 0.82855(5) 0.01894(15) Uani 1 1 d . . . O2 O 0.8538(2) 0.63121(9) 0.65694(18) 0.0174(3) Uani 1 1 d . . . O1 O 0.6819(2) 0.48496(11) 0.21232(15) 0.0169(3) Uani 1 1 d . . . O3 O 0.7143(2) 0.34197(10) 0.6376(2) 0.0167(3) Uani 1 1 d . . . C1 C 0.7139(3) 0.48745(11) 0.3538(2) 0.0134(4) Uani 1 1 d . . . C3 C 0.8019(3) 0.56056(11) 0.5801(2) 0.0134(4) Uani 1 1 d . . . C2 C 0.7648(3) 0.56027(11) 0.4334(2) 0.0130(4) Uani 1 1 d . . . C6 C 0.6980(3) 0.41382(11) 0.4231(2) 0.0142(4) Uani 1 1 d . . . C5 C 0.7313(3) 0.41246(11) 0.5690(2) 0.0132(4) Uani 1 1 d . . . C4 C 0.7855(3) 0.48614(11) 0.64607(19) 0.0136(4) Uani 1 1 d . . . O6 O 0.8947(3) 0.68233(14) 0.9341(2) 0.0243(4) Uani 1 1 d . . . O5 O 0.6942(3) 0.29788(15) 0.9029(2) 0.0248(4) Uani 1 1 d . . . O4 O 0.5870(3) 0.60907(11) 0.0158(2) 0.0221(4) Uani 1 1 d . . . H1A H 0.674(5) 0.528(2) 0.175(4) 0.034(11) Uiso 0.73 1 d P . . H1B H 0.60(2) 0.448(9) 0.169(15) 0.08(5) Uiso 0.27 1 d P . . H2A H 0.833(6) 0.676(3) 0.613(4) 0.021(11) Uiso 0.60 1 d P . . H2B H 0.867(8) 0.630(3) 0.727(6) 0.005(15) Uiso 0.40 1 d P . . H3A H 0.679(6) 0.310(3) 0.598(4) 0.006(12) Uiso 0.60 1 d P . . H3B H 0.708(8) 0.345(3) 0.710(7) 0.017(17) Uiso 0.40 1 d P . . H4A H 0.683(4) 0.6343(17) 0.000(3) 0.031(7) Uiso 1 1 d . . . H4B H 0.519(5) 0.591(2) -0.051(4) 0.011(9) Uiso 0.73 1 d P . . H4C H 0.596(12) 0.570(6) 0.057(9) 0.01(2) Uiso 0.27 1 d P . . H5A H 0.607(5) 0.3212(18) 0.931(3) 0.051(9) Uiso 1 1 d . . . H5B H 0.684(6) 0.314(2) 0.827(5) 0.018(11) Uiso 0.60 1 d P . . H5C H 0.689(9) 0.262(4) 0.901(6) 0.000(19) Uiso 0.40 1 d P . . H6A H 1.010(5) 0.6809(17) 0.976(3) 0.035(9) Uiso 1 1 d . . . H6B H 0.890(6) 0.663(2) 0.865(5) 0.019(12) Uiso 0.60 1 d P . . H6C H 0.863(11) 0.721(5) 0.923(7) 0.03(3) Uiso 0.40 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 Cl2 0.0210(3) 0.0114(3) 0.0158(3) 0.00242(18) 0.0048(2) -0.00038(18) Cl3 0.0287(3) 0.0121(3) 0.0155(3) -0.00253(18) 0.0058(2) -0.00358(19) Cl1 0.0299(3) 0.0146(3) 0.0127(3) -0.00035(18) 0.0077(2) -0.0021(2) O2 0.0279(9) 0.0108(8) 0.0125(8) -0.0006(7) 0.0058(7) -0.0013(6) O1 0.0228(8) 0.0139(8) 0.0119(7) 0.0007(6) 0.0032(6) -0.0023(6) O3 0.0251(9) 0.0111(8) 0.0142(9) -0.0006(7) 0.0070(7) -0.0036(7) C1 0.0092(9) 0.0156(10) 0.0139(10) 0.0011(8) 0.0019(8) 0.0026(8) C3 0.0105(9) 0.0126(10) 0.0167(10) -0.0030(8) 0.0043(8) 0.0002(7) C2 0.0124(9) 0.0112(10) 0.0149(10) 0.0046(7) 0.0040(8) 0.0022(7) C6 0.0142(10) 0.0100(9) 0.0175(10) -0.0021(8) 0.0041(8) -0.0003(8) C5 0.0097(9) 0.0130(10) 0.0168(10) 0.0024(8) 0.0044(8) 0.0007(8) C4 0.0143(10) 0.0160(10) 0.0100(10) -0.0004(7) 0.0036(8) 0.0013(8) O6 0.0253(11) 0.0224(11) 0.0202(10) 0.0037(8) 0.0012(8) -0.0017(8) O5 0.0290(10) 0.0219(12) 0.0206(11) -0.0036(9) 0.0049(7) 0.0064(9) O4 0.0311(10) 0.0178(9) 0.0179(10) -0.0012(8) 0.0090(8) -0.0039(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 Cl2 C2 1.7329(18) . ? Cl3 C6 1.7291(19) . ? Cl1 C4 1.7319(18) . ? O2 C3 1.347(2) . ? O2 H2A 0.83(4) . ? O2 H2B 0.67(5) . ? O1 C1 1.349(2) . ? O1 H1A 0.78(4) . ? O1 H1B 0.83(16) . ? O3 C5 1.348(2) . ? O3 H3A 0.65(4) . ? O3 H3B 0.74(6) . ? C1 C2 1.389(3) . ? C1 C6 1.392(3) . ? C3 C4 1.387(3) . ? C3 C2 1.393(3) . ? C6 C5 1.390(3) . ? C5 C4 1.390(3) . ? O6 H6A 0.76(3) . ? O6 H6B 0.75(4) . ? O6 H6C 0.65(8) . ? O5 H5A 0.84(3) . ? O5 H5B 0.78(4) . ? O5 H5C 0.58(6) . ? O4 H4A 0.84(3) . ? O4 H4B 0.73(4) . ? O4 H4C 0.74(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 C3 O2 H2A 118(3) . . ? C3 O2 H2B 119(5) . . ? H2A O2 H2B 120(5) . . ? C1 O1 H1A 115(3) . . ? C1 O1 H1B 114(9) . . ? H1A O1 H1B 117(9) . . ? C5 O3 H3A 116(3) . . ? C5 O3 H3B 119(4) . . ? H3A O3 H3B 121(5) . . ? O1 C1 C2 122.65(17) . . ? O1 C1 C6 118.65(17) . . ? C2 C1 C6 118.69(17) . . ? O2 C3 C4 120.39(17) . . ? O2 C3 C2 121.08(17) . . ? C4 C3 C2 118.53(17) . . ? C1 C2 C3 121.38(16) . . ? C1 C2 Cl2 119.71(14) . . ? C3 C2 Cl2 118.91(14) . . ? C5 C6 C1 121.18(17) . . ? C5 C6 Cl3 119.04(14) . . ? C1 C6 Cl3 119.78(15) . . ? O3 C5 C6 122.04(18) . . ? O3 C5 C4 119.24(18) . . ? C6 C5 C4 118.72(16) . . ? C3 C4 C5 121.48(17) . . ? C3 C4 Cl1 119.22(14) . . ? C5 C4 Cl1 119.31(14) . . ? H6A O6 H6B 101(4) . . ? H6A O6 H6C 111(7) . . ? H6B O6 H6C 110(7) . . ? H5A O5 H5B 110(3) . . ? H5A O5 H5C 114(6) . . ? H5B O5 H5C 109(7) . . ? H4A O4 H4B 109(3) . . ? H4A O4 H4C 126(6) . . ? H4B O4 H4C 95(7) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.354 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.067