# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Enrico Dalcanale' _publ_contact_author_email ENRICO.DALCANALE@UNIPR.IT _publ_section_title ; Formation of tetrameric water clusters driven by a cavitand template ; loop_ _publ_author_name 'Enrico Dalcanale' 'Chiara Massera' 'Monica Melegari' 'Franco Ugozzoli' # Attachment 'total_revised.cif' data_tpoiw4 _database_code_depnum_ccdc_archive 'CCDC 737537' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H44 O16 P4' _chemical_formula_weight 856.59 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M P4/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y+1/2, x, z' 'y, -x+1/2, z' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y-1/2, -x, -z' '-y, x-1/2, -z' _cell_length_a 14.396(8) _cell_length_b 14.396(8) _cell_length_c 9.799(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2030.8(19) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2256 _cell_measurement_theta_min 1.41 _cell_measurement_theta_max 27.57 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.256 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.791071 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details 'Bruker AXS SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS Smart 1000' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean '8.192 pixel/mm' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11151 _diffrn_reflns_av_R_equivalents 0.0994 _diffrn_reflns_av_sigmaI/netI 0.1207 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 27.57 _reflns_number_total 2354 _reflns_number_gt 1187 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement ? _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SIR97 (Giacovazzo et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. Restraints on the water molecules were added in the last cycle of refinement to prevent the oscillations of the maximum shift value. ; _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^)+(0.0180P)^2^+0.0000P] 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 0.0034(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2354 _refine_ls_number_parameters 140 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1166 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.0846 _refine_ls_wR_factor_gt 0.0765 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.009 _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 P1 P 0.16715(8) 0.56848(7) 0.71546(10) 0.0424(3) Uani 1 1 d . . . O3 O 0.18539(18) 0.5049(2) 0.6039(3) 0.0594(9) Uani 1 1 d . . . O1 O 0.25348(17) 0.58656(16) 0.8124(2) 0.0411(7) Uani 1 1 d . . . O2 O 0.08402(17) 0.53965(17) 0.8131(3) 0.0424(7) Uani 1 1 d . . . C1 C 0.0927(3) 0.3415(3) 1.0439(3) 0.0373(10) Uani 1 1 d . . . H1 H 0.1227 0.3239 1.1239 0.020(9) Uiso 1 1 calc R . . C2 C 0.0279(2) 0.2812(3) 0.9864(4) 0.0368(9) Uani 1 1 d . . . C3 C -0.0146(3) 0.3093(3) 0.8673(4) 0.0380(10) Uani 1 1 d . . . C4 C 0.0029(3) 0.3938(3) 0.8015(4) 0.0369(9) Uani 1 1 d . . . C5 C 0.0691(3) 0.4502(2) 0.8678(4) 0.0353(9) Uani 1 1 d . . . C6 C 0.1138(3) 0.4263(3) 0.9865(4) 0.0363(9) Uani 1 1 d . . . C7 C -0.0429(3) 0.4230(3) 0.6719(4) 0.0511(12) Uani 1 1 d . . . H7A H -0.0623 0.4866 0.6792 0.097(7) Uiso 1 1 calc R . . H7B H -0.0962 0.3844 0.6555 0.097(7) Uiso 1 1 calc R . . H7C H 0.0001 0.4167 0.5976 0.097(7) Uiso 1 1 calc R . . C8 C 0.1878(3) 0.4885(3) 1.0501(4) 0.0415(11) Uani 1 1 d . . . H8A H 0.1704 0.5531 1.0379 0.031(6) Uiso 1 1 calc R . . H8B H 0.1914 0.4763 1.1473 0.031(6) Uiso 1 1 calc R . . C9 C 0.1344(3) 0.6830(3) 0.6728(4) 0.0598(13) Uani 1 1 d . . . H9A H 0.1778 0.7080 0.6081 0.097(7) Uiso 1 1 calc R . . H9B H 0.1344 0.7207 0.7536 0.097(7) Uiso 1 1 calc R . . H9C H 0.0733 0.6825 0.6336 0.097(7) Uiso 1 1 calc R . . O1W O 0.2212(3) 0.3874(3) 0.3823(3) 0.0895(12) Uani 1 1 d D . . H1W H 0.193(3) 0.425(3) 0.456(3) 0.134 Uiso 1 1 d D . . H2W H 0.2845(15) 0.375(4) 0.413(4) 0.134 Uiso 1 1 d 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 P1 0.0410(7) 0.0349(7) 0.0512(6) 0.0014(6) 0.0011(6) 0.0021(6) O3 0.057(2) 0.066(2) 0.0548(18) -0.0197(17) 0.0047(16) 0.0012(17) O1 0.0375(16) 0.0334(16) 0.0523(18) 0.0008(13) -0.0029(14) 0.0034(12) O2 0.0363(16) 0.0323(16) 0.0586(19) 0.0035(13) 0.0064(14) 0.0020(13) C1 0.037(3) 0.044(3) 0.031(2) -0.003(2) 0.0028(19) 0.005(2) C2 0.031(2) 0.041(3) 0.039(2) 0.002(2) 0.007(2) 0.0048(19) C3 0.033(2) 0.038(3) 0.043(3) -0.005(2) 0.007(2) 0.004(2) C4 0.033(2) 0.038(3) 0.040(3) -0.001(2) 0.007(2) 0.0048(19) C5 0.033(2) 0.030(3) 0.042(2) 0.0014(19) 0.011(2) 0.003(2) C6 0.035(2) 0.036(3) 0.038(3) -0.010(2) 0.006(2) 0.006(2) C7 0.040(3) 0.051(3) 0.061(3) 0.007(3) -0.010(2) 0.001(2) C8 0.047(3) 0.037(3) 0.040(3) -0.008(2) 0.005(2) 0.004(2) C9 0.053(3) 0.040(3) 0.087(3) 0.029(2) -0.005(2) -0.001(2) O1W 0.110(3) 0.080(3) 0.078(3) -0.007(2) 0.006(2) 0.012(3) _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 P1 O3 1.449(3) . ? P1 O1 1.586(3) . ? P1 O2 1.587(3) . ? P1 C9 1.764(4) . ? O1 C3 1.417(4) 4 ? O2 C5 1.412(4) . ? C1 C6 1.379(5) . ? C1 C2 1.393(5) . ? C1 H1 0.9300 . ? C2 C3 1.378(5) . ? C2 C8 1.501(4) 3 ? C3 C4 1.400(5) . ? C3 O1 1.417(4) 3 ? C4 C5 1.411(5) . ? C4 C7 1.491(5) . ? C5 C6 1.372(4) . ? C6 C8 1.526(5) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C2 1.501(4) 4 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? O1W H1W 0.993(10) . ? O1W H2W 0.975(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 O3 P1 O1 114.41(16) . . ? O3 P1 O2 115.20(16) . . ? O1 P1 O2 105.83(14) . . ? O3 P1 C9 117.38(18) . . ? O1 P1 C9 101.41(17) . . ? O2 P1 C9 100.69(18) . . ? C3 O1 P1 123.5(2) 4 . ? C5 O2 P1 125.6(2) . . ? C6 C1 C2 122.2(4) . . ? C6 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? C3 C2 C1 117.3(4) . . ? C3 C2 C8 123.0(3) . 3 ? C1 C2 C8 119.6(4) . 3 ? C2 C3 C4 124.4(4) . . ? C2 C3 O1 118.7(3) . 3 ? C4 C3 O1 116.7(3) . 3 ? C3 C4 C5 114.2(3) . . ? C3 C4 C7 123.9(3) . . ? C5 C4 C7 122.0(3) . . ? C6 C5 C4 124.3(4) . . ? C6 C5 O2 118.6(3) . . ? C4 C5 O2 116.9(3) . . ? C5 C6 C1 117.7(4) . . ? C5 C6 C8 121.8(4) . . ? C1 C6 C8 120.5(3) . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C2 C8 C6 111.3(3) 4 . ? C2 C8 H8A 109.4 4 . ? C6 C8 H8A 109.4 . . ? C2 C8 H8B 109.4 4 . ? C6 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? P1 C9 H9A 109.5 . . ? P1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? P1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? H1W O1W H2W 104.9(14) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.423 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.057 #Data for compound 2 data_tpometaq _database_code_depnum_ccdc_archive 'CCDC 737538' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H48 O17 P4' _chemical_formula_weight 888.63 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M P4/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y+1/2, x, z' 'y, -x+1/2, z' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y-1/2, -x, -z' '-y, x-1/2, -z' _cell_length_a 14.352(2) _cell_length_b 14.352(2) _cell_length_c 9.8218(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2023.2(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2045 _cell_measurement_theta_min 2.01 _cell_measurement_theta_max 29.03 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 932 _exptl_absorpt_coefficient_mu 0.262 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.782580 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details 'Bruker AXS SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER AXS SMART 1000' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean '8.192 pixels/mm' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12598 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 29.03 _reflns_number_total 2626 _reflns_number_gt 1836 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement ? _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SIR97 (Giacovazzo et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1008P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2626 _refine_ls_number_parameters 144 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0657 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1509 _refine_ls_wR_factor_gt 0.1417 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 P1 P 0.43165(3) -0.16861(3) 0.71664(6) 0.0448(2) Uani 1 1 d . . . O1 O 0.45877(9) -0.08494(9) 0.81278(15) 0.0472(3) Uani 1 1 d . . . O2 O 0.41318(9) -0.25606(9) 0.81200(16) 0.0472(3) Uani 1 1 d . . . O3 O 0.49896(12) -0.18675(12) 0.60892(17) 0.0666(5) Uani 1 1 d . . . C1 C 0.65755(13) -0.09328(13) 1.0433(2) 0.0434(4) Uani 1 1 d . . . H1 H 0.6758 -0.1232 1.1230 0.050(6) Uiso 1 1 calc R . . C2 C 0.57193(13) -0.11510(12) 0.9863(2) 0.0416(4) Uani 1 1 d . . . C3 C 0.54816(12) -0.06912(12) 0.8670(2) 0.0415(4) Uani 1 1 d . . . C4 C 0.60366(13) -0.00350(12) 0.8032(2) 0.0423(4) Uani 1 1 d . . . C5 C 0.68829(13) 0.01501(12) 0.8667(2) 0.0413(4) Uani 1 1 d . . . C6 C 0.71681(13) -0.02825(13) 0.98542(19) 0.0425(4) Uani 1 1 d . . . C7 C 0.57420(15) 0.04328(15) 0.6736(2) 0.0550(5) Uani 1 1 d . . . H7A H 0.5908 0.0048 0.5975 0.103(4) Uiso 1 1 calc R . . H7B H 0.6050 0.1024 0.6659 0.103(4) Uiso 1 1 calc R . . H7C H 0.5080 0.0526 0.6745 0.103(4) Uiso 1 1 calc R . . C8 C 0.51020(13) -0.18863(13) 1.0484(2) 0.0458(4) Uani 1 1 d . . . H8A H 0.4454 -0.1717 1.0346 0.048(4) Uiso 1 1 calc R . . H8B H 0.5215 -0.1918 1.1456 0.048(4) Uiso 1 1 calc R . . C9 C 0.31783(16) -0.13599(17) 0.6698(3) 0.0665(7) Uani 1 1 d . . . H9A H 0.3179 -0.0724 0.6393 0.103(4) Uiso 1 1 calc R . . H9B H 0.2772 -0.1421 0.7468 0.103(4) Uiso 1 1 calc R . . H9C H 0.2964 -0.1756 0.5975 0.103(4) Uiso 1 1 calc R . . O1W O 0.60799(19) -0.2282(2) 0.3796(3) 0.1259(10) Uani 1 1 d . . . C1S C 0.7500 -0.2500 0.7423(9) 0.111(2) Uani 1 4 d SD . . O1S O 0.7025(13) -0.216(2) 0.6279(9) 0.158(6) Uani 0.25 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 P1 0.0389(3) 0.0468(3) 0.0486(3) -0.0029(2) 0.0002(2) 0.00226(19) O1 0.0377(7) 0.0459(7) 0.0579(8) -0.0062(6) -0.0009(6) 0.0037(5) O2 0.0366(6) 0.0475(7) 0.0575(8) 0.0003(6) 0.0023(6) 0.0018(5) O3 0.0753(11) 0.0679(10) 0.0568(10) -0.0058(8) 0.0178(8) 0.0003(8) C1 0.0499(10) 0.0457(9) 0.0345(8) -0.0072(8) 0.0026(8) 0.0050(8) C2 0.0445(9) 0.0420(9) 0.0384(9) -0.0093(7) 0.0082(7) 0.0038(7) C3 0.0371(8) 0.0412(9) 0.0461(10) -0.0092(8) 0.0010(7) 0.0045(7) C4 0.0453(9) 0.0372(8) 0.0444(10) -0.0052(7) -0.0009(8) 0.0045(7) C5 0.0445(9) 0.0341(8) 0.0452(10) -0.0074(7) 0.0013(8) 0.0005(7) C6 0.0465(10) 0.0419(9) 0.0393(9) -0.0124(8) 0.0021(8) 0.0024(7) C7 0.0583(12) 0.0499(11) 0.0567(13) 0.0058(10) -0.0074(10) -0.0018(9) C8 0.0471(10) 0.0515(10) 0.0386(9) -0.0055(8) 0.0109(8) 0.0018(8) C9 0.0518(12) 0.0641(14) 0.0835(18) 0.0039(12) -0.0205(12) -0.0015(10) O1W 0.119(2) 0.180(3) 0.0780(16) 0.0085(17) 0.0128(15) 0.0401(18) C1S 0.118(4) 0.118(4) 0.097(5) 0.000 0.000 0.000 O1S 0.114(11) 0.193(17) 0.166(11) 0.070(13) 0.054(10) 0.060(8) _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 P1 O3 1.4562(16) . ? P1 O1 1.5765(14) . ? P1 O2 1.5883(15) . ? P1 C9 1.761(2) . ? O1 C3 1.408(2) . ? O2 C5 1.410(2) 3_545 ? C1 C6 1.385(3) . ? C1 C2 1.386(3) . ? C1 H1 0.9300 . ? C2 C3 1.387(3) . ? C2 C8 1.507(3) . ? C3 C4 1.383(3) . ? C4 C5 1.391(3) . ? C4 C7 1.500(3) . ? C5 C6 1.383(3) . ? C5 O2 1.410(2) 4_655 ? C6 C8 1.514(3) 4_655 ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C6 1.514(3) 3_545 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C1S O1S 1.3994(10) 3_545 ? C1S O1S 1.3994(10) . ? C1S O1S 1.3994(10) 4_655 ? C1S O1S 1.3994(10) 2_645 ? O1S O1S 1.180(14) 3_545 ? O1S O1S 1.180(14) 4_655 ? O1S O1S 1.669(19) 2_645 ? 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 O3 P1 O1 114.06(9) . . ? O3 P1 O2 113.45(9) . . ? O1 P1 O2 106.86(8) . . ? O3 P1 C9 118.23(13) . . ? O1 P1 C9 100.55(10) . . ? O2 P1 C9 102.09(10) . . ? C3 O1 P1 125.07(11) . . ? C5 O2 P1 123.39(11) 3_545 . ? C6 C1 C2 122.05(19) . . ? C6 C1 H1 119.0 . . ? C2 C1 H1 119.0 . . ? C1 C2 C3 116.86(18) . . ? C1 C2 C8 121.08(18) . . ? C3 C2 C8 122.01(17) . . ? C4 C3 C2 124.37(18) . . ? C4 C3 O1 117.59(17) . . ? C2 C3 O1 117.85(17) . . ? C3 C4 C5 115.46(18) . . ? C3 C4 C7 121.78(18) . . ? C5 C4 C7 122.75(18) . . ? C6 C5 C4 123.41(18) . . ? C6 C5 O2 118.80(17) . 4_655 ? C4 C5 O2 117.61(17) . 4_655 ? C5 C6 C1 117.85(18) . . ? C5 C6 C8 122.20(18) . 4_655 ? C1 C6 C8 119.88(18) . 4_655 ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C2 C8 C6 111.24(15) . 3_545 ? C2 C8 H8A 109.4 . . ? C6 C8 H8A 109.4 3_545 . ? C2 C8 H8B 109.4 . . ? C6 C8 H8B 109.4 3_545 . ? H8A C8 H8B 108.0 . . ? P1 C9 H9A 109.5 . . ? P1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? P1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O1S C1S O1S 49.9(6) 3_545 . ? O1S C1S O1S 73.2(10) 3_545 4_655 ? O1S C1S O1S 49.9(6) . 4_655 ? O1S C1S O1S 49.9(6) 3_545 2_645 ? O1S C1S O1S 73.2(10) . 2_645 ? O1S C1S O1S 49.9(6) 4_655 2_645 ? O1S O1S O1S 90.000(3) 3_545 4_655 ? O1S O1S C1S 65.1(3) 3_545 . ? O1S O1S C1S 65.1(3) 4_655 . ? O1S O1S O1S 45.000(2) 3_545 2_645 ? O1S O1S O1S 45.000(2) 4_655 2_645 ? C1S O1S O1S 53.4(5) . 2_645 ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 29.03 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.549 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.063 #Data for compound 3 data_tglicole _database_code_depnum_ccdc_archive 'CCDC 737539' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H54 Cl4 O18 P4' _chemical_formula_weight 1088.51 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' P P 0.1023 0.0942 '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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3676(4) _cell_length_b 13.1307(5) _cell_length_c 19.1132(8) _cell_angle_alpha 69.9800(10) _cell_angle_beta 88.7130(10) _cell_angle_gamma 82.9350(10) _cell_volume 2425.63(17) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10405 _cell_measurement_theta_min 1.13 _cell_measurement_theta_max 28.98 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1132 _exptl_absorpt_coefficient_mu 0.448 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.747528 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details 'Bruker AXS SADABS' _exptl_special_details ; The calculated molar mass, density and absorption coefficient include two disordered dicholomethane molecules per cell which do not appear in the final files because of the refinements carried out with data subjected to SQUEEZE. See "_refine_special_details" below. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER AXS SMART 1000' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean '8.192 pixels/mm' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 25175 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0627 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.13 _diffrn_reflns_theta_max 28.98 _reflns_number_total 11553 _reflns_number_gt 7160 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement ? _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SIR97 (Giacovazzo et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. In view of the presence of a disordered dichloromethane molecule which could not be properly modelled, the structure was subjected to SQUEEZE (P. v.d. Sluis and A. L. Spek, Acta Crystallogr., Sect A 1990, 46, 194-201). The program calculated a void volume of 247.7 A^3^ and 80 electrons per unit cell, which correspond to two dichloromethane molecules per unit cell. some restraints on the water molecule were added in the last cycle of refinement to prevent the oscillations of the maximum shift value. ; _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^)+(0.0671P)^2^+0.0000P] 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 11553 _refine_ls_number_parameters 611 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0802 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.1368 _refine_ls_wR_factor_gt 0.1288 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _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 P1A P 0.17467(6) -0.21698(6) 0.52194(4) 0.03230(17) Uani 1 1 d . . . O1A O 0.11421(17) -0.32609(15) 0.53226(9) 0.0326(4) Uani 1 1 d . . . O2A O 0.06368(16) -0.11787(15) 0.48627(9) 0.0333(4) Uani 1 1 d . . . O3A O 0.29551(17) -0.20711(17) 0.48046(10) 0.0400(5) Uani 1 1 d . . . C1A C -0.0316(2) -0.3837(2) 0.37923(13) 0.0277(5) Uani 1 1 d . . . H1A H -0.1050 -0.3596 0.3481 0.027(3) Uiso 1 1 calc R . . C2A C -0.0116(2) -0.3322(2) 0.42998(13) 0.0275(5) Uani 1 1 d . . . C3A C 0.0989(2) -0.3700(2) 0.47518(13) 0.0282(5) Uani 1 1 d . . . C4A C 0.1918(2) -0.4541(2) 0.47163(13) 0.0293(5) Uani 1 1 d . . . C5A C 0.1645(2) -0.5018(2) 0.41962(13) 0.0282(5) Uani 1 1 d . . . C6A C 0.0549(2) -0.4701(2) 0.37356(13) 0.0267(5) Uani 1 1 d . . . C7A C 0.3114(3) -0.4923(2) 0.52079(15) 0.0385(6) Uani 1 1 d . . . H7A1 H 0.3284 -0.5704 0.5366 0.068(2) Uiso 1 1 calc R . . H7A2 H 0.2982 -0.4701 0.5636 0.068(2) Uiso 1 1 calc R . . H7A3 H 0.3841 -0.4606 0.4937 0.068(2) Uiso 1 1 calc R . . C8A C -0.1052(2) -0.2368(2) 0.43384(13) 0.0305(6) Uani 1 1 d . . . H8A1 H -0.1105 -0.2380 0.4849 0.041(2) Uiso 1 1 calc R . . H8A2 H -0.1912 -0.2421 0.4175 0.041(2) Uiso 1 1 calc R . . C9A C 0.1817(3) -0.2201(3) 0.61543(15) 0.0444(7) Uani 1 1 d . . . H9A1 H 0.2333 -0.2860 0.6453 0.068(2) Uiso 1 1 calc R . . H9A2 H 0.0954 -0.2180 0.6346 0.068(2) Uiso 1 1 calc R . . H9A3 H 0.2203 -0.1581 0.6170 0.068(2) Uiso 1 1 calc R . . P1B P 0.19277(7) 0.15057(6) 0.18607(4) 0.03109(16) Uani 1 1 d . . . O1B O 0.07810(17) 0.15281(14) 0.24237(9) 0.0329(4) Uani 1 1 d . . . O2B O 0.13070(16) 0.14611(13) 0.11220(9) 0.0305(4) Uani 1 1 d . . . O3B O 0.29813(17) 0.06337(16) 0.21880(11) 0.0408(5) Uani 1 1 d . . . C1B C -0.0969(2) -0.0875(2) 0.31001(13) 0.0277(5) Uani 1 1 d . . . H1B H -0.1545 -0.1220 0.2920 0.027(3) Uiso 1 1 calc R . . C2B C -0.0519(2) 0.0057(2) 0.26134(13) 0.0271(5) Uani 1 1 d . . . C3B C 0.0353(2) 0.0543(2) 0.28986(14) 0.0288(5) Uani 1 1 d . . . C4B C 0.0786(2) 0.0152(2) 0.36441(13) 0.0295(5) Uani 1 1 d . . . C5B C 0.0287(2) -0.0779(2) 0.40964(13) 0.0293(5) Uani 1 1 d . . . C6B C -0.0592(2) -0.1311(2) 0.38466(13) 0.0280(5) Uani 1 1 d . . . C7B C 0.1740(3) 0.0697(2) 0.39296(15) 0.0376(6) Uani 1 1 d . . . H7B1 H 0.1462 0.0743 0.4402 0.068(2) Uiso 1 1 calc R . . H7B2 H 0.1786 0.1419 0.3581 0.068(2) Uiso 1 1 calc R . . H7B3 H 0.2583 0.0279 0.3989 0.068(2) Uiso 1 1 calc R . . C8B C -0.0948(2) 0.0499(2) 0.17974(13) 0.0286(5) Uani 1 1 d . . . H8B1 H -0.1820 0.0329 0.1753 0.041(2) Uiso 1 1 calc R . . H8B2 H -0.0971 0.1288 0.1612 0.041(2) Uiso 1 1 calc R . . C9B C 0.2301(3) 0.2862(2) 0.15755(17) 0.0460(7) Uani 1 1 d . . . H9B1 H 0.2707 0.2981 0.1982 0.068(2) Uiso 1 1 calc R . . H9B2 H 0.1516 0.3358 0.1424 0.068(2) Uiso 1 1 calc R . . H9B3 H 0.2882 0.2984 0.1165 0.068(2) Uiso 1 1 calc R . . P1C P 0.35030(6) -0.22562(6) 0.02107(4) 0.02970(16) Uani 1 1 d . . . O1C O 0.23927(16) -0.12562(14) -0.00262(9) 0.0285(4) Uani 1 1 d . . . O2C O 0.28070(16) -0.33341(14) 0.04430(9) 0.0309(4) Uani 1 1 d . . . O3C O 0.44250(18) -0.22460(16) 0.07732(10) 0.0412(5) Uani 1 1 d . . . C1C C -0.0288(2) -0.09078(19) 0.11863(12) 0.0244(5) Uani 1 1 d . . . H1C H -0.1020 -0.1235 0.1389 0.027(3) Uiso 1 1 calc R . . C2C C 0.0521(2) -0.13629(19) 0.07504(12) 0.0242(5) Uani 1 1 d . . . C3C C 0.1612(2) -0.08542(19) 0.04618(12) 0.0253(5) Uani 1 1 d . . . C4C C 0.1932(2) 0.0067(2) 0.05854(13) 0.0260(5) Uani 1 1 d . . . C5C C 0.1075(2) 0.04754(19) 0.10256(12) 0.0244(5) Uani 1 1 d . . . C6C C -0.0037(2) 0.0015(2) 0.13278(12) 0.0254(5) Uani 1 1 d . . . C7C C 0.3107(3) 0.0597(2) 0.02470(15) 0.0362(6) Uani 1 1 d . . . H7C1 H 0.3875 0.0169 0.0514 0.068(2) Uiso 1 1 calc R . . H7C2 H 0.3040 0.1318 0.0276 0.068(2) Uiso 1 1 calc R . . H7C3 H 0.3158 0.0645 -0.0265 0.068(2) Uiso 1 1 calc R . . C8C C 0.0229(2) -0.23920(19) 0.06260(13) 0.0271(5) Uani 1 1 d . . . H8C1 H -0.0700 -0.2432 0.0653 0.041(2) Uiso 1 1 calc R . . H8C2 H 0.0508 -0.2377 0.0135 0.041(2) Uiso 1 1 calc R . . C9C C 0.4123(3) -0.2216(3) -0.06665(15) 0.0444(7) Uani 1 1 d . . . H9C1 H 0.4475 -0.1540 -0.0900 0.068(2) Uiso 1 1 calc R . . H9C2 H 0.3436 -0.2270 -0.0975 0.068(2) Uiso 1 1 calc R . . H9C3 H 0.4795 -0.2815 -0.0600 0.068(2) Uiso 1 1 calc R . . P1D P 0.35958(6) -0.59529(6) 0.36058(4) 0.02997(16) Uani 1 1 d . . . O1D O 0.28959(16) -0.60400(13) 0.28966(9) 0.0301(4) Uani 1 1 d . . . O2D O 0.24904(16) -0.59472(14) 0.41916(9) 0.0310(4) Uani 1 1 d . . . O3D O 0.43421(18) -0.50261(16) 0.34203(10) 0.0419(5) Uani 1 1 d . . . C1D C 0.0341(2) -0.38822(19) 0.18827(13) 0.0253(5) Uani 1 1 d . . . H1D H -0.0512 -0.3623 0.1949 0.027(3) Uiso 1 1 calc R . . C2D C 0.0975(2) -0.4755(2) 0.24538(13) 0.0257(5) Uani 1 1 d . . . C3D C 0.2256(2) -0.51076(19) 0.23410(13) 0.0262(5) Uani 1 1 d . . . C4D C 0.2916(2) -0.4653(2) 0.16855(13) 0.0277(5) Uani 1 1 d . . . C5D C 0.2212(2) -0.3781(2) 0.11366(13) 0.0274(5) Uani 1 1 d . . . C6D C 0.0935(2) -0.33825(19) 0.12159(13) 0.0251(5) Uani 1 1 d . . . C7D C 0.4291(2) -0.5061(2) 0.15728(15) 0.0355(6) Uani 1 1 d . . . H7D1 H 0.4383 -0.5056 0.1071 0.068(2) Uiso 1 1 calc R . . H7D2 H 0.4505 -0.5792 0.1914 0.068(2) Uiso 1 1 calc R . . H7D3 H 0.4865 -0.4596 0.1662 0.068(2) Uiso 1 1 calc R . . C8D C 0.0303(2) -0.5254(2) 0.31816(13) 0.0270(5) Uani 1 1 d . . . H8D1 H 0.0618 -0.6026 0.3392 0.041(2) Uiso 1 1 calc R . . H8D2 H -0.0625 -0.5185 0.3088 0.041(2) Uiso 1 1 calc R . . C9D C 0.4420(3) -0.7284(2) 0.40065(16) 0.0454(7) Uani 1 1 d . . . H9D1 H 0.5020 -0.7439 0.3656 0.068(2) Uiso 1 1 calc R . . H9D2 H 0.3802 -0.7803 0.4134 0.068(2) Uiso 1 1 calc R . . H9D3 H 0.4887 -0.7333 0.4448 0.068(2) Uiso 1 1 calc R . . C1S C 0.3397(3) -0.2161(3) 0.23396(16) 0.0468(7) Uani 1 1 d . . . H1S1 H 0.3996 -0.2806 0.2376 0.041(2) Uiso 1 1 calc R . . H1S2 H 0.2665 -0.2141 0.2026 0.041(2) Uiso 1 1 calc R . . C2S C 0.2927(3) -0.2240(3) 0.30921(18) 0.0505(8) Uani 1 1 d . . . H2S1 H 0.2313 -0.1604 0.3060 0.041(2) Uiso 1 1 calc R . . H2S2 H 0.2487 -0.2885 0.3299 0.041(2) Uiso 1 1 calc R . . O1S O 0.4040(2) -0.12038(19) 0.19982(13) 0.0586(6) Uani 1 1 d D . . O2S O 0.4001(3) -0.2301(3) 0.35626(14) 0.0832(9) Uani 1 1 d D . . O1W O 0.6768(2) -0.4476(2) 0.28135(14) 0.0599(6) Uani 1 1 d D . . O2W O 0.6530(2) -0.2613(2) 0.32460(15) 0.0676(7) Uani 1 1 d D . . O3W O 0.6586(3) -0.1179(3) 0.1805(2) 0.0920(9) Uani 1 1 d D . . O4W O 0.6906(2) -0.3039(3) 0.13591(15) 0.0776(8) Uani 1 1 d D . . C3S C 0.5577(3) 0.0069(3) 0.32272(18) 0.0527(8) Uani 1 1 d . . . H3S1 H 0.4679 0.0009 0.3133 0.041(2) Uiso 1 1 calc R . . H3S2 H 0.6122 -0.0491 0.3096 0.041(2) Uiso 1 1 calc R . . Cl1 Cl 0.58006(10) -0.01544(8) 0.41722(5) 0.0679(3) Uani 1 1 d . . . Cl2 Cl 0.59571(9) 0.13545(8) 0.26634(4) 0.0629(2) Uani 1 1 d . . . H1S H 0.359(5) -0.060(3) 0.211(3) 0.150 Uiso 1 1 d D . . H2S H 0.373(5) -0.238(5) 0.4057(13) 0.150 Uiso 1 1 d D . . H3W H 0.654(3) -0.217(3) 0.2762(9) 0.123 Uiso 1 1 d D . . H1W H 0.604(2) -0.481(3) 0.295(2) 0.095 Uiso 1 1 d D . . H5W H 0.5715(13) -0.095(5) 0.175(3) 0.150 Uiso 1 1 d D . . H7W H 0.6070(15) -0.277(4) 0.122(3) 0.150 Uiso 1 1 d D . . H8W H 0.691(4) -0.363(3) 0.1779(18) 0.150 Uiso 1 1 d D . . H4W H 0.5682(12) -0.257(3) 0.3381(18) 0.086(13) Uiso 1 1 d D . . H6W H 0.667(5) -0.178(3) 0.167(3) 0.130 Uiso 1 1 d D . . H2W H 0.674(4) -0.396(3) 0.303(3) 0.14(2) Uiso 1 1 d 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 P1A 0.0333(3) 0.0437(4) 0.0225(3) -0.0138(3) 0.0028(3) -0.0079(3) O1A 0.0378(10) 0.0399(11) 0.0205(8) -0.0100(8) 0.0035(7) -0.0079(8) O2A 0.0355(9) 0.0431(11) 0.0242(9) -0.0155(8) 0.0033(7) -0.0048(8) O3A 0.0345(10) 0.0539(13) 0.0335(10) -0.0163(9) 0.0044(8) -0.0092(9) C1A 0.0260(12) 0.0335(14) 0.0210(12) -0.0042(10) 0.0015(9) -0.0089(10) C2A 0.0259(12) 0.0323(14) 0.0212(11) -0.0038(10) 0.0081(9) -0.0095(10) C3A 0.0320(13) 0.0336(14) 0.0192(11) -0.0077(10) 0.0052(9) -0.0105(11) C4A 0.0312(13) 0.0346(15) 0.0196(11) -0.0038(10) 0.0037(9) -0.0105(11) C5A 0.0307(12) 0.0282(14) 0.0226(12) -0.0037(10) 0.0057(9) -0.0073(10) C6A 0.0275(12) 0.0261(13) 0.0236(12) -0.0029(10) 0.0058(9) -0.0105(10) C7A 0.0387(15) 0.0424(17) 0.0323(14) -0.0103(12) -0.0045(11) -0.0033(13) C8A 0.0258(12) 0.0404(16) 0.0261(12) -0.0120(11) 0.0055(10) -0.0061(11) C9A 0.0504(17) 0.058(2) 0.0291(14) -0.0205(14) -0.0017(12) -0.0074(15) P1B 0.0373(4) 0.0257(4) 0.0330(4) -0.0123(3) 0.0007(3) -0.0077(3) O1B 0.0415(10) 0.0264(10) 0.0331(10) -0.0125(8) 0.0030(8) -0.0059(8) O2B 0.0397(10) 0.0219(9) 0.0285(9) -0.0068(7) -0.0002(7) -0.0039(8) O3B 0.0373(10) 0.0406(12) 0.0476(11) -0.0196(9) -0.0080(9) -0.0018(9) C1B 0.0215(11) 0.0327(14) 0.0319(13) -0.0155(11) 0.0038(9) -0.0018(10) C2B 0.0265(12) 0.0283(14) 0.0274(12) -0.0123(11) 0.0029(9) 0.0011(10) C3B 0.0310(13) 0.0262(14) 0.0300(13) -0.0110(11) 0.0061(10) -0.0034(10) C4B 0.0292(12) 0.0342(15) 0.0303(13) -0.0176(11) 0.0032(10) -0.0045(11) C5B 0.0311(13) 0.0346(15) 0.0251(12) -0.0149(11) 0.0035(10) -0.0014(11) C6B 0.0237(11) 0.0316(14) 0.0302(13) -0.0138(11) 0.0053(9) 0.0002(10) C7B 0.0448(15) 0.0416(17) 0.0322(14) -0.0179(13) 0.0042(12) -0.0125(13) C8B 0.0258(12) 0.0279(14) 0.0306(13) -0.0092(11) -0.0011(10) -0.0005(10) C9B 0.065(2) 0.0347(17) 0.0455(17) -0.0177(14) 0.0132(15) -0.0226(15) P1C 0.0307(3) 0.0324(4) 0.0243(3) -0.0081(3) 0.0039(3) -0.0026(3) O1C 0.0334(9) 0.0304(10) 0.0205(8) -0.0081(7) 0.0036(7) -0.0024(7) O2C 0.0368(9) 0.0300(10) 0.0239(9) -0.0083(7) 0.0070(7) -0.0009(8) O3C 0.0375(10) 0.0465(12) 0.0369(10) -0.0108(9) -0.0034(8) -0.0045(9) C1C 0.0230(11) 0.0262(13) 0.0203(11) -0.0028(10) -0.0036(9) -0.0033(10) C2C 0.0286(12) 0.0213(12) 0.0202(11) -0.0045(9) -0.0069(9) 0.0004(10) C3C 0.0295(12) 0.0255(13) 0.0181(11) -0.0047(10) -0.0005(9) -0.0003(10) C4C 0.0256(12) 0.0268(13) 0.0227(12) -0.0055(10) -0.0026(9) -0.0008(10) C5C 0.0312(12) 0.0195(12) 0.0195(11) -0.0030(9) -0.0049(9) -0.0014(10) C6C 0.0246(12) 0.0263(13) 0.0224(12) -0.0057(10) -0.0039(9) 0.0010(10) C7C 0.0376(14) 0.0350(16) 0.0356(14) -0.0091(12) 0.0055(11) -0.0122(12) C8C 0.0292(12) 0.0252(13) 0.0268(12) -0.0087(10) -0.0030(10) -0.0034(10) C9C 0.0512(17) 0.0458(18) 0.0354(15) -0.0138(14) 0.0173(13) -0.0063(14) P1D 0.0309(3) 0.0281(4) 0.0291(3) -0.0075(3) -0.0010(3) -0.0032(3) O1D 0.0357(9) 0.0229(9) 0.0282(9) -0.0050(7) -0.0030(7) -0.0009(7) O2D 0.0350(9) 0.0260(10) 0.0279(9) -0.0048(7) 0.0008(7) -0.0016(8) O3D 0.0402(10) 0.0461(12) 0.0420(11) -0.0147(9) 0.0030(8) -0.0160(9) C1D 0.0256(12) 0.0253(13) 0.0286(12) -0.0129(10) -0.0011(9) -0.0059(10) C2D 0.0320(12) 0.0242(13) 0.0241(12) -0.0102(10) 0.0007(9) -0.0099(10) C3D 0.0332(13) 0.0192(12) 0.0263(12) -0.0076(10) -0.0055(10) -0.0025(10) C4D 0.0309(13) 0.0247(13) 0.0288(13) -0.0111(10) 0.0011(10) -0.0035(10) C5D 0.0349(13) 0.0257(13) 0.0230(12) -0.0091(10) 0.0037(10) -0.0068(11) C6D 0.0290(12) 0.0246(13) 0.0246(12) -0.0113(10) -0.0016(9) -0.0050(10) C7D 0.0334(14) 0.0323(15) 0.0392(15) -0.0116(12) 0.0047(11) -0.0007(12) C8D 0.0284(12) 0.0254(13) 0.0267(12) -0.0069(10) 0.0011(9) -0.0081(10) C9D 0.0446(16) 0.0427(18) 0.0419(16) -0.0098(14) -0.0094(13) 0.0097(14) C1S 0.0595(19) 0.0424(18) 0.0375(16) -0.0133(14) -0.0043(14) -0.0023(15) C2S 0.0463(17) 0.054(2) 0.0527(19) -0.0201(16) 0.0071(15) -0.0073(15) O1S 0.0654(15) 0.0456(14) 0.0628(15) -0.0173(12) 0.0128(12) -0.0050(12) O2S 0.0638(16) 0.153(3) 0.0494(14) -0.0531(18) 0.0083(12) -0.0232(17) O1W 0.0462(13) 0.0771(18) 0.0585(15) -0.0243(14) 0.0052(11) -0.0127(12) O2W 0.0435(14) 0.083(2) 0.0829(18) -0.0363(16) 0.0000(12) -0.0099(13) O3W 0.0708(18) 0.112(3) 0.099(2) -0.037(2) 0.0135(18) -0.0321(19) O4W 0.0464(13) 0.095(2) 0.0698(18) -0.0026(15) -0.0031(12) -0.0037(14) C3S 0.0458(17) 0.056(2) 0.066(2) -0.0367(18) -0.0045(15) 0.0033(15) Cl1 0.0832(6) 0.0643(6) 0.0473(5) -0.0082(4) -0.0011(4) -0.0066(5) Cl2 0.0733(6) 0.0810(7) 0.0371(4) -0.0217(4) 0.0044(4) -0.0155(5) _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 P1A O3A 1.4628(19) . ? P1A O1A 1.5832(19) . ? P1A O2A 1.5944(19) . ? P1A C9A 1.776(3) . ? O1A C3A 1.418(3) . ? O2A C5B 1.415(3) . ? C1A C2A 1.391(3) . ? C1A C6A 1.390(3) . ? C1A H1A 0.9300 . ? C2A C3A 1.384(3) . ? C2A C8A 1.510(3) . ? C3A C4A 1.392(4) . ? C4A C5A 1.393(3) . ? C4A C7A 1.499(3) . ? C5A C6A 1.385(3) . ? C5A O2D 1.415(3) . ? C6A C8D 1.516(3) . ? C7A H7A1 0.9600 . ? C7A H7A2 0.9600 . ? C7A H7A3 0.9600 . ? C8A C6B 1.512(4) . ? C8A H8A1 0.9700 . ? C8A H8A2 0.9700 . ? C9A H9A1 0.9600 . ? C9A H9A2 0.9600 . ? C9A H9A3 0.9600 . ? P1B O3B 1.4587(19) . ? P1B O2B 1.5869(17) . ? P1B O1B 1.5898(18) . ? P1B C9B 1.764(3) . ? O1B C3B 1.419(3) . ? O2B C5C 1.417(3) . ? C1B C2B 1.386(3) . ? C1B C6B 1.388(3) . ? C1B H1B 0.9300 . ? C2B C3B 1.388(3) . ? C2B C8B 1.522(3) . ? C3B C4B 1.402(3) . ? C4B C5B 1.386(4) . ? C4B C7B 1.502(3) . ? C5B C6B 1.397(3) . ? C7B H7B1 0.9600 . ? C7B H7B2 0.9600 . ? C7B H7B3 0.9600 . ? C8B C6C 1.519(3) . ? C8B H8B1 0.9700 . ? C8B H8B2 0.9700 . ? C9B H9B1 0.9600 . ? C9B H9B2 0.9600 . ? C9B H9B3 0.9600 . ? P1C O3C 1.4590(19) . ? P1C O1C 1.5807(18) . ? P1C O2C 1.5899(19) . ? P1C C9C 1.768(3) . ? O1C C3C 1.415(3) . ? O2C C5D 1.415(3) . ? C1C C6C 1.384(3) . ? C1C C2C 1.393(3) . ? C1C H1C 0.9300 . ? C2C C3C 1.391(3) . ? C2C C8C 1.516(3) . ? C3C C4C 1.388(3) . ? C4C C5C 1.394(3) . ? C4C C7C 1.501(3) . ? C5C C6C 1.389(3) . ? C7C H7C1 0.9600 . ? C7C H7C2 0.9600 . ? C7C H7C3 0.9600 . ? C8C C6D 1.516(3) . ? C8C H8C1 0.9700 . ? C8C H8C2 0.9700 . ? C9C H9C1 0.9600 . ? C9C H9C2 0.9600 . ? C9C H9C3 0.9600 . ? P1D O3D 1.4592(19) . ? P1D O2D 1.5853(18) . ? P1D O1D 1.5961(17) . ? P1D C9D 1.765(3) . ? O1D C3D 1.417(3) . ? C1D C6D 1.388(3) . ? C1D C2D 1.388(3) . ? C1D H1D 0.9300 . ? C2D C3D 1.389(3) . ? C2D C8D 1.515(3) . ? C3D C4D 1.394(3) . ? C4D C5D 1.396(3) . ? C4D C7D 1.497(3) . ? C5D C6D 1.387(3) . ? C7D H7D1 0.9600 . ? C7D H7D2 0.9600 . ? C7D H7D3 0.9600 . ? C8D H8D1 0.9700 . ? C8D H8D2 0.9700 . ? C9D H9D1 0.9600 . ? C9D H9D2 0.9600 . ? C9D H9D3 0.9600 . ? C1S O1S 1.440(4) . ? C1S C2S 1.482(4) . ? C1S H1S1 0.9700 . ? C1S H1S2 0.9700 . ? C2S O2S 1.424(4) . ? C2S H2S1 0.9700 . ? C2S H2S2 0.9700 . ? O1S H1S 0.956(10) . ? O2S H2S 0.953(10) . ? O1W H1W 0.903(5) . ? O1W H2W 0.904(5) . ? O2W H3W 0.909(5) . ? O2W H4W 0.912(5) . ? O3W H5W 0.911(5) . ? O3W H6W 0.907(5) . ? O4W H7W 0.903(5) . ? O4W H8W 0.902(5) . ? C3S Cl1 1.744(3) . ? C3S Cl2 1.751(4) . ? C3S H3S1 0.9700 . ? C3S H3S2 0.9700 . ? 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 O3A P1A O1A 114.05(11) . . ? O3A P1A O2A 113.56(11) . . ? O1A P1A O2A 107.25(10) . . ? O3A P1A C9A 117.42(13) . . ? O1A P1A C9A 101.24(12) . . ? O2A P1A C9A 101.81(12) . . ? C3A O1A P1A 125.22(15) . . ? C5B O2A P1A 123.19(15) . . ? C2A C1A C6A 122.0(2) . . ? C2A C1A H1A 119.0 . . ? C6A C1A H1A 119.0 . . ? C3A C2A C1A 117.4(2) . . ? C3A C2A C8A 121.6(2) . . ? C1A C2A C8A 121.0(2) . . ? C2A C3A C4A 124.1(2) . . ? C2A C3A O1A 118.1(2) . . ? C4A C3A O1A 117.6(2) . . ? C3A C4A C5A 115.0(2) . . ? C3A C4A C7A 122.8(2) . . ? C5A C4A C7A 122.2(2) . . ? C6A C5A C4A 124.3(2) . . ? C6A C5A O2D 118.4(2) . . ? C4A C5A O2D 117.1(2) . . ? C5A C6A C1A 117.2(2) . . ? C5A C6A C8D 121.9(2) . . ? C1A C6A C8D 121.0(2) . . ? C4A C7A H7A1 109.5 . . ? C4A C7A H7A2 109.5 . . ? H7A1 C7A H7A2 109.5 . . ? C4A C7A H7A3 109.5 . . ? H7A1 C7A H7A3 109.5 . . ? H7A2 C7A H7A3 109.5 . . ? C2A C8A C6B 109.63(19) . . ? C2A C8A H8A1 109.7 . . ? C6B C8A H8A1 109.7 . . ? C2A C8A H8A2 109.7 . . ? C6B C8A H8A2 109.7 . . ? H8A1 C8A H8A2 108.2 . . ? P1A C9A H9A1 109.5 . . ? P1A C9A H9A2 109.5 . . ? H9A1 C9A H9A2 109.5 . . ? P1A C9A H9A3 109.5 . . ? H9A1 C9A H9A3 109.5 . . ? H9A2 C9A H9A3 109.5 . . ? O3B P1B O2B 113.93(10) . . ? O3B P1B O1B 112.67(11) . . ? O2B P1B O1B 107.61(9) . . ? O3B P1B C9B 117.43(14) . . ? O2B P1B C9B 101.98(12) . . ? O1B P1B C9B 101.91(12) . . ? C3B O1B P1B 120.69(15) . . ? C5C O2B P1B 123.29(14) . . ? C2B C1B C6B 122.5(2) . . ? C2B C1B H1B 118.7 . . ? C6B C1B H1B 118.7 . . ? C1B C2B C3B 117.2(2) . . ? C1B C2B C8B 120.7(2) . . ? C3B C2B C8B 122.1(2) . . ? C2B C3B C4B 123.8(2) . . ? C2B C3B O1B 118.5(2) . . ? C4B C3B O1B 117.6(2) . . ? C5B C4B C3B 115.5(2) . . ? C5B C4B C7B 122.3(2) . . ? C3B C4B C7B 122.1(2) . . ? C4B C5B C6B 123.7(2) . . ? C4B C5B O2A 118.0(2) . . ? C6B C5B O2A 118.2(2) . . ? C1B C6B C5B 117.2(2) . . ? C1B C6B C8A 120.0(2) . . ? C5B C6B C8A 122.7(2) . . ? C4B C7B H7B1 109.5 . . ? C4B C7B H7B2 109.5 . . ? H7B1 C7B H7B2 109.5 . . ? C4B C7B H7B3 109.5 . . ? H7B1 C7B H7B3 109.5 . . ? H7B2 C7B H7B3 109.5 . . ? C6C C8B C2B 111.53(19) . . ? C6C C8B H8B1 109.3 . . ? C2B C8B H8B1 109.3 . . ? C6C C8B H8B2 109.3 . . ? C2B C8B H8B2 109.3 . . ? H8B1 C8B H8B2 108.0 . . ? P1B C9B H9B1 109.5 . . ? P1B C9B H9B2 109.5 . . ? H9B1 C9B H9B2 109.5 . . ? P1B C9B H9B3 109.5 . . ? H9B1 C9B H9B3 109.5 . . ? H9B2 C9B H9B3 109.5 . . ? O3C P1C O1C 114.97(10) . . ? O3C P1C O2C 113.52(10) . . ? O1C P1C O2C 106.89(9) . . ? O3C P1C C9C 117.43(13) . . ? O1C P1C C9C 101.13(12) . . ? O2C P1C C9C 101.20(12) . . ? C3C O1C P1C 126.12(14) . . ? C5D O2C P1C 124.22(15) . . ? C6C C1C C2C 122.2(2) . . ? C6C C1C H1C 118.9 . . ? C2C C1C H1C 118.9 . . ? C3C C2C C1C 117.2(2) . . ? C3C C2C C8C 122.3(2) . . ? C1C C2C C8C 120.4(2) . . ? C4C C3C C2C 123.9(2) . . ? C4C C3C O1C 118.0(2) . . ? C2C C3C O1C 118.0(2) . . ? C3C C4C C5C 115.6(2) . . ? C3C C4C C7C 121.7(2) . . ? C5C C4C C7C 122.7(2) . . ? C6C C5C C4C 123.7(2) . . ? C6C C5C O2B 118.4(2) . . ? C4C C5C O2B 117.7(2) . . ? C1C C6C C5C 117.5(2) . . ? C1C C6C C8B 120.8(2) . . ? C5C C6C C8B 121.7(2) . . ? C4C C7C H7C1 109.5 . . ? C4C C7C H7C2 109.5 . . ? H7C1 C7C H7C2 109.5 . . ? C4C C7C H7C3 109.5 . . ? H7C1 C7C H7C3 109.5 . . ? H7C2 C7C H7C3 109.5 . . ? C6D C8C C2C 109.49(18) . . ? C6D C8C H8C1 109.8 . . ? C2C C8C H8C1 109.8 . . ? C6D C8C H8C2 109.8 . . ? C2C C8C H8C2 109.8 . . ? H8C1 C8C H8C2 108.2 . . ? P1C C9C H9C1 109.5 . . ? P1C C9C H9C2 109.5 . . ? H9C1 C9C H9C2 109.5 . . ? P1C C9C H9C3 109.5 . . ? H9C1 C9C H9C3 109.5 . . ? H9C2 C9C H9C3 109.5 . . ? O3D P1D O2D 114.28(11) . . ? O3D P1D O1D 112.96(10) . . ? O2D P1D O1D 106.11(9) . . ? O3D P1D C9D 118.71(14) . . ? O2D P1D C9D 101.41(12) . . ? O1D P1D C9D 101.71(12) . . ? C3D O1D P1D 121.79(14) . . ? C5A O2D P1D 125.30(15) . . ? C6D C1D C2D 122.3(2) . . ? C6D C1D H1D 118.8 . . ? C2D C1D H1D 118.8 . . ? C3D C2D C1D 117.3(2) . . ? C3D C2D C8D 122.1(2) . . ? C1D C2D C8D 120.6(2) . . ? C2D C3D C4D 123.7(2) . . ? C2D C3D O1D 118.2(2) . . ? C4D C3D O1D 117.8(2) . . ? C3D C4D C5D 115.6(2) . . ? C3D C4D C7D 122.7(2) . . ? C5D C4D C7D 121.8(2) . . ? C6D C5D C4D 123.6(2) . . ? C6D C5D O2C 118.3(2) . . ? C4D C5D O2C 117.9(2) . . ? C1D C6D C5D 117.4(2) . . ? C1D C6D C8C 120.4(2) . . ? C5D C6D C8C 122.1(2) . . ? C4D C7D H7D1 109.5 . . ? C4D C7D H7D2 109.5 . . ? H7D1 C7D H7D2 109.5 . . ? C4D C7D H7D3 109.5 . . ? H7D1 C7D H7D3 109.5 . . ? H7D2 C7D H7D3 109.5 . . ? C2D C8D C6A 111.37(19) . . ? C2D C8D H8D1 109.4 . . ? C6A C8D H8D1 109.4 . . ? C2D C8D H8D2 109.4 . . ? C6A C8D H8D2 109.4 . . ? H8D1 C8D H8D2 108.0 . . ? P1D C9D H9D1 109.5 . . ? P1D C9D H9D2 109.5 . . ? H9D1 C9D H9D2 109.5 . . ? P1D C9D H9D3 109.5 . . ? H9D1 C9D H9D3 109.5 . . ? H9D2 C9D H9D3 109.5 . . ? O1S C1S C2S 112.2(3) . . ? O1S C1S H1S1 109.2 . . ? C2S C1S H1S1 109.2 . . ? O1S C1S H1S2 109.2 . . ? C2S C1S H1S2 109.2 . . ? H1S1 C1S H1S2 107.9 . . ? O2S C2S C1S 109.5(3) . . ? O2S C2S H2S1 109.8 . . ? C1S C2S H2S1 109.8 . . ? O2S C2S H2S2 109.8 . . ? C1S C2S H2S2 109.8 . . ? H2S1 C2S H2S2 108.2 . . ? C1S O1S H1S 110(3) . . ? C2S O2S H2S 112(3) . . ? H1W O1W H2W 107.6(8) . . ? H3W O2W H4W 106.0(8) . . ? H5W O3W H6W 103(5) . . ? H7W O4W H8W 108.1(8) . . ? Cl1 C3S Cl2 112.22(17) . . ? Cl1 C3S H3S1 109.2 . . ? Cl2 C3S H3S1 109.2 . . ? Cl1 C3S H3S2 109.2 . . ? Cl2 C3S H3S2 109.2 . . ? H3S1 C3S H3S2 107.9 . . ? _diffrn_measured_fraction_theta_max 0.898 _diffrn_reflns_theta_full 28.98 _diffrn_measured_fraction_theta_full 0.898 _refine_diff_density_max 0.709 _refine_diff_density_min -0.415 _refine_diff_density_rms 0.071