# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_y _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C0 H2 In N0 O6 P2' _chemical_formula_weight 274.78 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' In In -0.7276 1.3100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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 Trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 9.1367(2) _cell_length_b 9.1367(2) _cell_length_c 25.9692(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1877.45(9) _cell_formula_units_Z 9 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2790 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 28.29 _exptl_crystal_description ? _exptl_crystal_colour ? _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 2.187 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1161 _exptl_absorpt_coefficient_mu 3.186 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5278 _exptl_absorpt_correction_T_max 0.5978 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 5.0cm _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4650 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 28.29 _reflns_number_total 1046 _reflns_number_gt 955 _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^)+(0.0167P)^2^+0.8910P] 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 1046 _refine_ls_number_parameters 55 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0176 _refine_ls_R_factor_gt 0.0159 _refine_ls_wR_factor_ref 0.0388 _refine_ls_wR_factor_gt 0.0385 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.000 _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 In1 In 0.0000 0.0000 0.0000 0.01513(9) Uani 1 6 d S . . In2 In 0.6667 0.3333 0.145971(8) 0.01561(8) Uani 1 3 d S . . P1 P 0.29102(8) 0.11111(13) 0.09562(2) 0.0179(2) Uani 0.859(3) 1 d PDU . . P1' P 0.2883(5) 0.0214(8) 0.09308(14) 0.0182(13) Uani 0.141(3) 1 d PU . . O1 O 0.2128(2) 0.0378(2) 0.04431(6) 0.0373(4) Uani 1 1 d . . . O2 O 0.47438(17) 0.15048(18) 0.09660(5) 0.0223(3) Uani 1 1 d . . . O3 O 0.19103(18) -0.00280(19) 0.14079(5) 0.0260(3) Uani 1 1 d . . . H1P H 0.296(3) 0.2665(14) 0.0989(8) 0.031 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 In1 0.01805(11) 0.01805(11) 0.00929(14) 0.000 0.000 0.00903(6) In2 0.01737(9) 0.01737(9) 0.01208(12) 0.000 0.000 0.00868(5) P1 0.0166(3) 0.0222(5) 0.0143(3) -0.0011(2) -0.0011(2) 0.0093(3) P1' 0.0202(17) 0.018(3) 0.0154(16) -0.0020(13) 0.0008(12) 0.0086(14) O1 0.0289(9) 0.0596(12) 0.0227(8) -0.0030(8) -0.0096(6) 0.0217(8) O2 0.0168(7) 0.0268(8) 0.0202(7) -0.0051(6) -0.0019(5) 0.0086(6) O3 0.0237(7) 0.0281(8) 0.0246(7) -0.0003(6) 0.0063(6) 0.0117(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 In1 O1 2.1335(15) 11 ? In1 O1 2.1336(15) 12 ? In1 O1 2.1336(15) 10 ? In1 O1 2.1336(15) 3 ? In1 O1 2.1336(15) . ? In1 O1 2.1336(15) 2 ? In2 O3 2.1341(14) 14 ? In2 O3 2.1342(14) 15 ? In2 O3 2.1342(14) 13 ? In2 O2 2.1416(13) . ? In2 O2 2.1416(13) 3_665 ? In2 O2 2.1417(13) 2_655 ? P1 P1' 0.810(6) . ? P1 O1 1.5021(16) . ? P1 O2 1.5277(15) . ? P1 O3 1.5307(15) . ? P1 H1P 1.399(2) . ? P1' O3 1.476(4) . ? P1' O1 1.485(4) . ? P1' O2 1.511(4) . ? O3 In2 2.1342(14) 13 ? 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 In1 O1 93.65(6) 11 12 ? O1 In1 O1 93.65(6) 11 10 ? O1 In1 O1 93.65(6) 12 10 ? O1 In1 O1 86.35(6) 11 3 ? O1 In1 O1 180.00(6) 12 3 ? O1 In1 O1 86.35(6) 10 3 ? O1 In1 O1 86.35(6) 11 . ? O1 In1 O1 86.35(6) 12 . ? O1 In1 O1 180.0 10 . ? O1 In1 O1 93.65(6) 3 . ? O1 In1 O1 180.0 11 2 ? O1 In1 O1 86.35(6) 12 2 ? O1 In1 O1 86.35(6) 10 2 ? O1 In1 O1 93.65(6) 3 2 ? O1 In1 O1 93.65(6) . 2 ? O3 In2 O3 91.04(6) 14 15 ? O3 In2 O3 91.04(6) 14 13 ? O3 In2 O3 91.04(6) 15 13 ? O3 In2 O2 91.56(5) 14 . ? O3 In2 O2 177.33(5) 15 . ? O3 In2 O2 89.53(5) 13 . ? O3 In2 O2 177.33(5) 14 3_665 ? O3 In2 O2 89.53(5) 15 3_665 ? O3 In2 O2 91.56(5) 13 3_665 ? O2 In2 O2 87.84(5) . 3_665 ? O3 In2 O2 89.53(5) 14 2_655 ? O3 In2 O2 91.56(5) 15 2_655 ? O3 In2 O2 177.32(5) 13 2_655 ? O2 In2 O2 87.84(5) . 2_655 ? O2 In2 O2 87.84(5) 3_665 2_655 ? P1' P1 O1 73.1(3) . . ? P1' P1 O2 73.4(3) . . ? O1 P1 O2 109.94(9) . . ? P1' P1 O3 70.7(3) . . ? O1 P1 O3 112.80(10) . . ? O2 P1 O3 111.03(9) . . ? P1' P1 H1P 178.8(9) . . ? O1 P1 H1P 105.9(9) . . ? O2 P1 H1P 106.5(9) . . ? O3 P1 H1P 110.4(9) . . ? P1 P1' O3 78.2(3) . . ? P1 P1' O1 75.4(4) . . ? O3 P1' O1 117.1(3) . . ? P1 P1' O2 75.7(3) . . ? O3 P1' O2 115.1(3) . . ? O1 P1' O2 111.8(3) . . ? P1' O1 P1 31.5(2) . . ? P1' O1 In1 151.08(18) . . ? P1 O1 In1 137.95(11) . . ? P1' O2 P1 30.9(2) . . ? P1' O2 In2 143.98(18) . . ? P1 O2 In2 124.67(8) . . ? P1' O3 P1 31.2(2) . . ? P1' O3 In2 155.4(2) . 13 ? P1 O3 In2 129.78(9) . 13 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.511 _refine_diff_density_min -0.520 _refine_diff_density_rms 0.079 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.143 -0.063 0.370 655 233 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 961207' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_y _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H14 F In N2 O6 P2' _chemical_formula_weight 369.92 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' In In -0.7276 1.3100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.4121(10) _cell_length_b 10.2340(18) _cell_length_c 10.5108(19) _cell_angle_alpha 113.234(2) _cell_angle_beta 95.522(3) _cell_angle_gamma 92.534(2) _cell_volume 530.32(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1943 _cell_measurement_theta_min 3.60 _cell_measurement_theta_max 28.36 _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 2.557 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5909 _exptl_absorpt_correction_T_max 0.7490 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 5.0cm _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3305 _diffrn_reflns_av_R_equivalents 0.0179 _diffrn_reflns_av_sigmaI/netI 0.0329 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2060 _reflns_number_gt 1877 _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^)+(0.0263P)^2^+0.4281P] 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 2060 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0285 _refine_ls_R_factor_gt 0.0247 _refine_ls_wR_factor_ref 0.0592 _refine_ls_wR_factor_gt 0.0562 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 In1 In 0.72419(4) 0.26768(2) 0.40045(3) 0.01570(9) Uani 1 1 d . . . P1 P 0.28195(16) 0.38944(9) 0.60928(9) 0.01494(19) Uani 1 1 d . . . P2 P 0.17538(17) 0.24367(10) 0.19658(10) 0.0183(2) Uani 1 1 d . . . F1 F 0.7031(4) 0.0552(2) 0.3889(2) 0.0228(5) Uani 1 1 d . . . O1 O 0.1902(6) 0.2026(4) 0.0449(3) 0.0453(9) Uani 1 1 d . . . O2 O 0.3825(4) 0.1829(3) 0.2612(3) 0.0207(6) Uani 1 1 d . . . O3 O 0.5238(4) 0.3205(3) 0.5755(3) 0.0237(6) Uani 1 1 d . . . O4 O 0.2712(6) 0.5275(3) 0.5942(4) 0.0480(10) Uani 1 1 d . . . O5 O 0.0559(5) 0.2857(3) 0.5326(3) 0.0246(6) Uani 1 1 d . . . O6 O 0.9189(5) 0.1960(3) 0.2208(3) 0.0278(6) Uani 1 1 d . . . N1 N 0.1796(6) 0.9786(3) 0.3630(3) 0.0254(7) Uani 1 1 d . . . H1A H 0.2918 0.9672 0.4246 0.031 Uiso 1 1 d R . . H1B H 0.0403 1.0043 0.4013 0.031 Uiso 1 1 d R . . H1C H 0.2396 1.0461 0.3379 0.031 Uiso 1 1 d R . . N2 N 0.3901(6) 0.8832(3) 0.0753(3) 0.0269(7) Uani 1 1 d . . . H2A H 0.5298 0.8620 0.0361 0.032 Uiso 1 1 d R . . H2B H 0.4030 0.9754 0.1319 0.032 Uiso 1 1 d R . . H2C H 0.2620 0.8647 0.0091 0.032 Uiso 1 1 d R . . C1 C 0.1280(8) 0.8419(4) 0.2397(5) 0.0321(10) Uani 1 1 d . . . H1D H -0.0100 0.8503 0.1781 0.038 Uiso 1 1 calc R . . H1E H 0.0761 0.7681 0.2701 0.038 Uiso 1 1 calc R . . C2 C 0.3466(7) 0.7955(4) 0.1580(4) 0.0262(9) Uani 1 1 d . . . H2 H 0.4965 0.8069 0.2230 0.031 Uiso 1 1 calc R . . C3 C 0.2976(10) 0.6399(4) 0.0575(5) 0.0450(12) Uani 1 1 d . . . H3A H 0.1460 0.6272 -0.0032 0.067 Uiso 1 1 calc R . . H3B H 0.2822 0.5814 0.1092 0.067 Uiso 1 1 calc R . . H3C H 0.4336 0.6128 0.0030 0.067 Uiso 1 1 calc R . . H1P H 0.2728 0.4290 0.7435 0.067 Uiso 1 1 d R . . H2P H 0.2037 0.3927 0.2456 0.067 Uiso 1 1 d R . . 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 In1 0.00976(13) 0.01527(13) 0.02243(15) 0.00795(10) 0.00174(9) 0.00153(9) P1 0.0124(4) 0.0161(4) 0.0160(5) 0.0058(3) 0.0028(3) 0.0019(3) P2 0.0149(4) 0.0247(5) 0.0173(5) 0.0097(4) 0.0038(4) 0.0056(4) F1 0.0178(10) 0.0181(10) 0.0332(13) 0.0117(9) -0.0001(9) 0.0018(8) O1 0.0398(18) 0.084(3) 0.0233(17) 0.0298(16) 0.0140(14) 0.0250(18) O2 0.0131(12) 0.0235(13) 0.0258(14) 0.0113(11) -0.0021(10) 0.0021(10) O3 0.0145(12) 0.0335(15) 0.0259(15) 0.0136(12) 0.0055(11) 0.0079(11) O4 0.0340(18) 0.0276(16) 0.094(3) 0.0350(18) 0.0120(18) 0.0072(14) O5 0.0159(13) 0.0257(13) 0.0327(16) 0.0138(12) -0.0031(11) -0.0008(11) O6 0.0142(13) 0.0388(16) 0.0270(16) 0.0095(12) 0.0028(11) 0.0014(11) N1 0.0209(16) 0.0292(17) 0.0301(19) 0.0135(14) 0.0125(14) 0.0049(14) N2 0.0306(18) 0.0282(17) 0.0214(18) 0.0089(14) 0.0053(14) 0.0028(14) C1 0.025(2) 0.035(2) 0.035(2) 0.0138(19) 0.0046(18) -0.0052(18) C2 0.027(2) 0.0247(19) 0.029(2) 0.0122(17) 0.0026(17) 0.0056(16) C3 0.059(3) 0.026(2) 0.046(3) 0.011(2) 0.001(2) 0.008(2) _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 In1 O4 2.074(3) 2_666 ? In1 O5 2.116(2) 1_655 ? In1 O3 2.122(3) . ? In1 F1 2.127(2) . ? In1 O6 2.138(3) . ? In1 O2 2.156(2) . ? P1 O4 1.485(3) . ? P1 O5 1.514(2) . ? P1 O3 1.520(3) . ? P1 H1P 1.3118 . ? P2 O1 1.492(3) . ? P2 O6 1.529(3) 1_455 ? P2 O2 1.534(2) . ? P2 H2P 1.3999 . ? O4 In1 2.074(3) 2_666 ? O5 In1 2.116(2) 1_455 ? O6 P2 1.529(3) 1_655 ? N1 C1 1.476(5) . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? N2 C2 1.502(5) . ? N2 H2A 0.8900 . ? N2 H2B 0.8900 . ? N2 H2C 0.8900 . ? C1 C2 1.512(6) . ? C1 H1D 0.9700 . ? C1 H1E 0.9700 . ? C2 C3 1.517(5) . ? C2 H2 0.9800 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? 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 O4 In1 O5 100.82(11) 2_666 1_655 ? O4 In1 O3 92.90(12) 2_666 . ? O5 In1 O3 89.08(10) 1_655 . ? O4 In1 F1 177.30(10) 2_666 . ? O5 In1 F1 81.88(9) 1_655 . ? O3 In1 F1 87.02(9) . . ? O4 In1 O6 91.79(13) 2_666 . ? O5 In1 O6 91.17(10) 1_655 . ? O3 In1 O6 175.16(10) . . ? F1 In1 O6 88.23(10) . . ? O4 In1 O2 96.81(11) 2_666 . ? O5 In1 O2 162.36(9) 1_655 . ? O3 In1 O2 90.46(10) . . ? F1 In1 O2 80.49(8) . . ? O6 In1 O2 87.84(10) . . ? O4 P1 O5 112.70(16) . . ? O4 P1 O3 114.28(17) . . ? O5 P1 O3 111.84(15) . . ? O4 P1 H1P 101.8 . . ? O5 P1 H1P 107.7 . . ? O3 P1 H1P 107.7 . . ? O1 P2 O6 110.98(17) . 1_455 ? O1 P2 O2 111.03(17) . . ? O6 P2 O2 110.91(16) 1_455 . ? O1 P2 H2P 100.7 . . ? O6 P2 H2P 109.6 1_455 . ? O2 P2 H2P 113.2 . . ? P2 O2 In1 136.12(15) . . ? P1 O3 In1 133.01(16) . . ? P1 O4 In1 172.7(2) . 2_666 ? P1 O5 In1 140.55(16) . 1_455 ? P2 O6 In1 131.73(15) 1_655 . ? C1 N1 H1A 108.6 . . ? C1 N1 H1B 110.0 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1C 109.8 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C2 N2 H2A 110.0 . . ? C2 N2 H2B 109.1 . . ? H2A N2 H2B 109.5 . . ? C2 N2 H2C 109.2 . . ? H2A N2 H2C 109.5 . . ? H2B N2 H2C 109.5 . . ? N1 C1 C2 114.4(3) . . ? N1 C1 H1D 108.7 . . ? C2 C1 H1D 108.7 . . ? N1 C1 H1E 108.7 . . ? C2 C1 H1E 108.7 . . ? H1D C1 H1E 107.6 . . ? N2 C2 C1 111.1(3) . . ? N2 C2 C3 108.3(4) . . ? C1 C2 C3 110.1(4) . . ? N2 C2 H2 109.1 . . ? C1 C2 H2 109.1 . . ? C3 C2 H2 109.1 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2C O1 0.89 2.46 3.217(5) 142.9 2_565 N2 H2C O6 0.89 2.34 3.167(4) 153.9 2_665 N2 H2B O2 0.89 2.04 2.920(4) 172.4 1_565 N2 H2A O1 0.89 1.83 2.716(5) 173.2 2_665 N1 H1C O2 0.89 2.03 2.918(4) 173.9 1_565 N1 H1B O5 0.89 2.65 3.082(4) 110.9 1_565 N1 H1B F1 0.89 1.93 2.735(4) 150.4 1_465 N1 H1A F1 0.89 2.06 2.781(4) 137.5 2_666 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.824 _refine_diff_density_min -0.786 _refine_diff_density_rms 0.111 _database_code_depnum_ccdc_archive 'CCDC 961208' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_y _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'H3 In2 O9 P3' _chemical_formula_weight 469.57 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' In In -0.7276 1.3100 '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 Hexagonal _symmetry_space_group_name_H-M 'P6(3)/m ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x-y, x, z+1/2' '-y, x-y, z' '-x, -y, z+1/2' '-x+y, -x, z' 'y, -x+y, z+1/2' '-x, -y, -z' '-x+y, -x, -z-1/2' 'y, -x+y, -z' 'x, y, -z-1/2' 'x-y, x, -z' '-y, x-y, -z-1/2' _cell_length_a 8.2519(3) _cell_length_b 8.2519(3) _cell_length_c 7.6934(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 453.69(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2215 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 28.20 _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 5.636 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3572 _exptl_absorpt_correction_T_max 0.4140 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 5.0cm _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3308 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0151 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 28.20 _reflns_number_total 398 _reflns_number_gt 390 _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^)+(0.0239P)^2^+0.2635P] 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 0.043(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 398 _refine_ls_number_parameters 26 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0180 _refine_ls_R_factor_gt 0.0175 _refine_ls_wR_factor_ref 0.0437 _refine_ls_wR_factor_gt 0.0433 _refine_ls_goodness_of_fit_ref 1.233 _refine_ls_restrained_S_all 1.233 _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 In1 In 0.6667 0.3333 -0.04272(3) 0.01329(16) Uani 1 3 d S . . P1 P 0.34648(11) 0.04089(11) 0.2500 0.0118(2) Uani 1 2 d S . . O1 O 0.4212(2) 0.1513(2) 0.0846(2) 0.0213(4) Uani 1 1 d . . . O2 O 0.3727(3) -0.1317(3) 0.2500 0.0161(5) Uani 1 2 d S . . H1P H 0.1686 -0.0137 0.2500 0.024 Uiso 1 2 d 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 In1 0.01633(17) 0.01633(17) 0.00720(19) 0.000 0.000 0.00817(9) P1 0.0114(4) 0.0135(4) 0.0098(4) 0.000 0.000 0.0057(3) O1 0.0223(8) 0.0230(8) 0.0178(9) 0.0092(7) 0.0053(7) 0.0108(7) O2 0.0255(12) 0.0146(10) 0.0099(10) 0.000 0.000 0.0112(10) _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 In1 O1 2.0680(17) . ? In1 O1 2.0680(17) 3_655 ? In1 O1 2.0680(17) 5_665 ? In1 O2 2.2082(16) 9_665 ? In1 O2 2.2082(16) 7_655 ? In1 O2 2.2082(16) 2_554 ? In1 In1 3.1894(5) 8_665 ? P1 O1 1.5059(18) 10_556 ? P1 O1 1.5059(18) . ? P1 O2 1.544(2) . ? P1 H1P 1.3027 . ? O2 In1 2.2082(16) 7_655 ? O2 In1 2.2082(16) 2_545 ? 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 In1 O1 99.42(7) . 3_655 ? O1 In1 O1 99.42(7) . 5_665 ? O1 In1 O1 99.42(7) 3_655 5_665 ? O1 In1 O2 161.78(7) . 9_665 ? O1 In1 O2 94.18(7) 3_655 9_665 ? O1 In1 O2 90.18(8) 5_665 9_665 ? O1 In1 O2 94.18(8) . 7_655 ? O1 In1 O2 90.18(8) 3_655 7_655 ? O1 In1 O2 161.78(7) 5_665 7_655 ? O2 In1 O2 73.60(7) 9_665 7_655 ? O1 In1 O2 90.18(8) . 2_554 ? O1 In1 O2 161.78(7) 3_655 2_554 ? O1 In1 O2 94.18(7) 5_665 2_554 ? O2 In1 O2 73.60(7) 9_665 2_554 ? O2 In1 O2 73.60(7) 7_655 2_554 ? O1 In1 In1 118.26(5) . 8_665 ? O1 In1 In1 118.26(5) 3_655 8_665 ? O1 In1 In1 118.26(5) 5_665 8_665 ? O2 In1 In1 43.77(4) 9_665 8_665 ? O2 In1 In1 43.77(4) 7_655 8_665 ? O2 In1 In1 43.77(4) 2_554 8_665 ? O1 P1 O1 115.38(15) 10_556 . ? O1 P1 O2 110.74(9) 10_556 . ? O1 P1 O2 110.74(9) . . ? O1 P1 H1P 105.0 10_556 . ? O1 P1 H1P 105.0 . . ? O2 P1 H1P 109.6 . . ? P1 O1 In1 142.72(12) . . ? P1 O2 In1 131.25(6) . 7_655 ? P1 O2 In1 131.25(6) . 2_545 ? In1 O2 In1 92.47(9) 7_655 2_545 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.20 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.654 _refine_diff_density_min -1.279 _refine_diff_density_rms 0.136 _database_code_depnum_ccdc_archive 'CCDC 961209' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_y _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C0 H7 In4 N0 O24 P7' _chemical_formula_weight 1067.13 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' In In -0.7276 1.3100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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 Trigonal _symmetry_space_group_name_H-M P-3c1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'y, x, -z+1/2' '-x, -x+y, -z+1/2' 'x-y, -y, -z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-y, -x, z-1/2' 'x, x-y, z-1/2' '-x+y, y, z-1/2' _cell_length_a 13.8148(18) _cell_length_b 13.8148(18) _cell_length_c 18.612(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3076.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2849 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 28.10 _exptl_crystal_description ? _exptl_crystal_colour ? _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 2.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2000 _exptl_absorpt_coefficient_mu 3.403 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.5082 _exptl_absorpt_correction_T_max 0.5794 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 5.0cm _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17881 _diffrn_reflns_av_R_equivalents 0.0778 _diffrn_reflns_av_sigmaI/netI 0.0412 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 26.22 _reflns_number_total 2075 _reflns_number_gt 1695 _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^)+(0.0721P)^2^+6.6015P] 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 0.00011(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2075 _refine_ls_number_parameters 119 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1247 _refine_ls_wR_factor_gt 0.1198 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.181 _refine_ls_shift/su_mean 0.021 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 In1 In 1.0000 1.0000 0.2500 0.01995(10) Uani 1 6 d S . . In2 In 1.0000 1.0000 0.0000 0.01993(10) Uani 1 6 d S . . In3 In 0.560684(13) 0.706546(13) 0.039802(11) 0.02580(5) Uani 1 1 d . . . P1 P 0.50646(5) 0.87606(4) -0.05820(3) 0.02476(19) Uani 1 1 d D . . P2 P 0.80836(5) 0.83998(4) 0.12813(4) 0.02342(18) Uani 1 1 d D . . P3 P 0.3333 0.6667 0.14317(4) 0.0213(3) Uani 0.852(3) 3 d SPDU . . P3' P 0.3333 0.6667 0.1217(4) 0.0218(4) Uani 0.148(3) 3 d SPU . . O1 O 0.56736(15) 0.85479(14) 0.00202(13) 0.0394(7) Uani 1 1 d . . . O2 O 0.69127(14) 0.74460(14) -0.04385(10) 0.0309(6) Uani 1 1 d . . . O3 O 0.44158(15) 0.67514(17) 0.12007(12) 0.0439(7) Uani 1 1 d . . . O4 O 0.85451(14) 0.93179(15) 0.18472(10) 0.0302(6) Uani 1 1 d . . . O5 O 0.88393(14) 0.86104(14) 0.06363(10) 0.0289(6) Uani 1 1 d . . . O6 O 0.69326(15) 0.81806(16) 0.10719(12) 0.0423(7) Uani 1 1 d . . . O7 O 0.38529(14) 0.83273(15) -0.04247(12) 0.0374(6) Uani 1 1 d . . . O8 O 0.56642(15) 0.99818(15) -0.07807(11) 0.0363(6) Uani 1 1 d . . . H3P H 0.3333 0.6667 0.22111(4) 0.054 Uiso 1 3 d SD . . H1P H 0.5043(2) 0.81012(10) -0.11945(6) 0.054 Uiso 1 1 d D . . H2P H 0.79395(17) 0.73612(7) 0.15708(14) 0.054 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 In1 0.01798(12) 0.01798(12) 0.02389(19) 0.000 0.000 0.00899(6) In2 0.01583(12) 0.01583(12) 0.0281(2) 0.000 0.000 0.00792(6) In3 0.01550(6) 0.01666(7) 0.04453(11) -0.00291(7) -0.00321(7) 0.00751(5) P1 0.0182(2) 0.0154(2) 0.0395(4) -0.0040(2) 0.0036(2) 0.00755(17) P2 0.0155(2) 0.0180(2) 0.0321(3) 0.0018(2) 0.0001(2) 0.00485(18) P3 0.0201(3) 0.0201(3) 0.0237(5) 0.000 0.000 0.01006(16) P3' 0.0202(5) 0.0202(5) 0.0250(8) 0.000 0.000 0.0101(3) O1 0.0322(8) 0.0209(8) 0.0655(14) -0.0036(8) -0.0117(9) 0.0135(6) O2 0.0244(7) 0.0274(7) 0.0426(11) 0.0004(7) 0.0029(7) 0.0142(5) O3 0.0278(8) 0.0451(9) 0.0640(14) -0.0042(9) 0.0067(9) 0.0222(6) O4 0.0238(7) 0.0317(8) 0.0324(9) -0.0091(7) -0.0069(7) 0.0117(6) O5 0.0261(7) 0.0216(7) 0.0329(9) -0.0010(7) 0.0022(7) 0.0074(6) O6 0.0209(8) 0.0432(9) 0.0597(13) -0.0191(9) -0.0071(8) 0.0137(6) O7 0.0195(7) 0.0326(8) 0.0609(13) -0.0118(8) 0.0002(8) 0.0135(6) O8 0.0349(9) 0.0216(8) 0.0442(11) 0.0029(8) -0.0036(9) 0.0081(6) _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 In1 O4 2.1237(18) . ? In1 O4 2.1237(18) 5_765 ? In1 O4 2.1237(18) 4 ? In1 O4 2.1237(18) 6_675 ? In1 O4 2.1237(18) 2_765 ? In1 O4 2.1237(18) 3_675 ? In2 O5 2.1402(16) 9_655 ? In2 O5 2.1402(16) 2_765 ? In2 O5 2.1403(16) 7_775 ? In2 O5 2.1403(16) . ? In2 O5 2.1403(16) 8_565 ? In2 O5 2.1403(16) 3_675 ? In3 O3 2.101(2) . ? In3 O7 2.102(2) 3_565 ? In3 O8 2.1137(16) 9_655 ? In3 O6 2.1164(18) . ? In3 O1 2.123(2) . ? In3 O2 2.2376(19) . ? P1 O7 1.4980(19) . ? P1 O8 1.5071(19) . ? P1 O1 1.516(2) . ? P1 H1P 1.4501(14) . ? P2 O5 1.520(2) . ? P2 O4 1.5218(19) . ? P2 O6 1.513(2) . ? P2 H2P 1.4503(13) . ? P3 O3 1.503(2) 2_665 ? P3 O3 1.503(2) 3_565 ? P3 O3 1.503(2) . ? P3 H3P 1.4506(11) . ? P3' O3 1.441(2) 2_665 ? P3' O3 1.441(2) 3_565 ? P3' O3 1.441(2) . ? P3' H3P 1.850(8) . ? O7 In3 2.102(2) 2_665 ? O8 In3 2.1137(16) 8_565 ? 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 O4 In1 O4 176.62(12) . 5_765 ? O4 In1 O4 91.93(10) . 4 ? O4 In1 O4 90.51(7) 5_765 4 ? O4 In1 O4 87.14(12) . 6_675 ? O4 In1 O4 90.51(7) 5_765 6_675 ? O4 In1 O4 90.51(7) 4 6_675 ? O4 In1 O4 90.52(7) . 2_765 ? O4 In1 O4 91.93(10) 5_765 2_765 ? O4 In1 O4 87.14(12) 4 2_765 ? O4 In1 O4 176.62(12) 6_675 2_765 ? O4 In1 O4 90.52(7) . 3_675 ? O4 In1 O4 87.14(12) 5_765 3_675 ? O4 In1 O4 176.62(12) 4 3_675 ? O4 In1 O4 91.93(10) 6_675 3_675 ? O4 In1 O4 90.52(7) 2_765 3_675 ? O5 In2 O5 87.67(7) 9_655 2_765 ? O5 In2 O5 92.33(7) 9_655 7_775 ? O5 In2 O5 87.67(7) 2_765 7_775 ? O5 In2 O5 87.67(7) 9_655 . ? O5 In2 O5 92.33(7) 2_765 . ? O5 In2 O5 180.0 7_775 . ? O5 In2 O5 92.33(7) 9_655 8_565 ? O5 In2 O5 180.0 2_765 8_565 ? O5 In2 O5 92.33(7) 7_775 8_565 ? O5 In2 O5 87.67(7) . 8_565 ? O5 In2 O5 180.0 9_655 3_675 ? O5 In2 O5 92.33(7) 2_765 3_675 ? O5 In2 O5 87.67(7) 7_775 3_675 ? O5 In2 O5 92.33(7) . 3_675 ? O5 In2 O5 87.67(7) 8_565 3_675 ? O3 In3 O7 97.10(8) . 3_565 ? O3 In3 O8 87.91(9) . 9_655 ? O7 In3 O8 93.17(7) 3_565 9_655 ? O3 In3 O6 91.85(8) . . ? O7 In3 O6 169.50(8) 3_565 . ? O8 In3 O6 92.63(9) 9_655 . ? O3 In3 O1 94.96(9) . . ? O7 In3 O1 90.07(7) 3_565 . ? O8 In3 O1 175.38(8) 9_655 . ? O6 In3 O1 83.67(8) . . ? O3 In3 O2 178.27(7) . . ? O7 In3 O2 84.51(8) 3_565 . ? O8 In3 O2 92.66(8) 9_655 . ? O6 In3 O2 86.49(7) . . ? O1 In3 O2 84.37(8) . . ? O7 P1 O8 111.98(13) . . ? O7 P1 O1 113.31(12) . . ? O8 P1 O1 110.53(10) . . ? O7 P1 H1P 103.55(13) . . ? O8 P1 H1P 109.72(10) . . ? O1 P1 H1P 107.39(14) . . ? O5 P2 O4 115.19(9) . . ? O5 P2 O6 112.79(12) . . ? O4 P2 O6 107.78(13) . . ? O5 P2 H2P 102.95(14) . . ? O4 P2 H2P 111.12(13) . . ? O6 P2 H2P 106.67(12) . . ? O3 P3 O3 112.17(8) 2_665 3_565 ? O3 P3 O3 112.16(8) 2_665 . ? O3 P3 O3 112.16(8) 3_565 . ? O3 P3 H3P 106.62(9) 2_665 . ? O3 P3 H3P 106.62(9) 3_565 . ? O3 P3 H3P 106.62(9) . . ? O3 P3' O3 119.96(3) 2_665 3_565 ? O3 P3' O3 119.95(3) 2_665 . ? O3 P3' O3 119.95(3) 3_565 . ? O3 P3' H3P 91.2(3) 2_665 . ? O3 P3' H3P 91.2(3) 3_565 . ? O3 P3' H3P 91.2(3) . . ? P1 O1 In3 132.16(10) . . ? P3' O3 P3 15.4(3) . . ? P3' O3 In3 134.9(3) . . ? P3 O3 In3 149.93(15) . . ? P2 O4 In1 132.45(14) . . ? P2 O5 In2 138.01(12) . . ? P2 O6 In3 137.61(15) . . ? P1 O7 In3 135.95(12) . 2_665 ? P1 O8 In3 136.33(13) . 8_565 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.22 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 3.330 _refine_diff_density_min -0.801 _refine_diff_density_rms 0.195 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.047 0.363 0.750 446 171 ' ' 2 -0.026 0.353 0.250 446 171 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 961210'