Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 186 loop_ _publ_author_name _publ_author_address 'Hassfjell, Sindre' ; Department for Reservoir and Exploration Technology Institute for Energy Technology P.O. Box 40 N-2027 Kjeller, Norway ; 'Kongshaug, Kjell Ove' ; University of Oslo P.O. Box 1033 N-0315 Oslo, Norway ; 'Romming, Christian' ; University of Oslo P.O. Box 1033 N-0315 Oslo, Norway ; _publ_contact_author_name 'Dr Sindre Hassfjell' ; Department for Reservoir and Exploration Technology Institute for Energy Technology P.O. Box 40 N-2027 Kjeller, Norway ; _publ_contact_author_email sindre.hassfjell@ife.no _publ_contact_author_fax '+47 63 81 09 20' _publ_contact_author_phone '+47 63 80 61 84' _publ_contact_letter ? _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Synthesis, crystal structure and chemical stability of bismuth(III) complexed with H8DOTMP ; data_BiDOTMP _database_code_CSD 191713 _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bismuth 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetramethylene phosphonate ; _chemical_name_common 'Bi H4DOTMP' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H36 Bi N4 Na O16 P4' _chemical_formula_weight 848.30 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' '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' 'Bi' 'Bi' -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Na' 'Na' 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M P4/n _symmetry_Int_Tables_number 85 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 14.7168(3) _cell_length_b 14.7168(3) _cell_length_c 6.8864(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1491.49(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.889 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 836 _exptl_absorpt_coefficient_mu 6.211 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature '150(2) K' _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30660 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0161 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 40.28 _reflns_number_total 4647 _reflns_number_gt 4395 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0257P)^2^+0.2875P] 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 4647 _refine_ls_number_parameters 162 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0196 _refine_ls_R_factor_gt 0.0176 _refine_ls_wR_factor_ref 0.0456 _refine_ls_wR_factor_gt 0.0453 _refine_ls_goodness_of_fit_ref 1.151 _refine_ls_restrained_S_all 1.151 _refine_ls_shift/su_max 1.179 _refine_ls_shift/su_mean 0.042 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 Bi1 Bi 0.7500 0.7500 0.287474(11) 0.01117(2) Uani 1 4 d S . . P1 P 0.91713(2) 0.59146(2) 0.16565(5) 0.01476(5) Uani 1 1 d . . . O1 O 0.82140(7) 0.62164(7) 0.12061(15) 0.01862(16) Uani 1 1 d . . . O2 O 0.98982(7) 0.61247(7) 0.01644(16) 0.02050(17) Uani 1 1 d . . . O3 O 0.91722(8) 0.48622(7) 0.20697(16) 0.02179(18) Uani 1 1 d . . . H3C H 1.053(10) 0.421(10) 0.17(2) 0.18(6) Uiso 0.50 1 d P . . H3D H 0.963(3) 0.449(3) 0.139(8) 0.028(11) Uiso 0.50 1 d P . . N1 N 0.87079(7) 0.67232(7) 0.51381(15) 0.01539(16) Uani 1 1 d . . . C1 C 0.83176(9) 0.58781(9) 0.59883(19) 0.01779(19) Uani 1 1 d . . . H1A H 0.8703(18) 0.5662(18) 0.715(3) 0.019(5) Uiso 1 1 d . . . H1B H 0.8306(14) 0.5403(15) 0.494(4) 0.020(5) Uiso 1 1 d . . . C2 C 0.89921(9) 0.73581(10) 0.67100(19) 0.0186(2) Uani 1 1 d . . . H2A H 0.853(2) 0.737(2) 0.765(4) 0.028(7) Uiso 1 1 d . . . H2B H 0.958(2) 0.714(2) 0.730(3) 0.024(6) Uiso 1 1 d . . . C3 C 0.94993(8) 0.64829(9) 0.39079(19) 0.01764(19) Uani 1 1 d . . . H3A H 0.9828(16) 0.6974(16) 0.351(4) 0.024(5) Uiso 1 1 d . . . H3B H 0.990(2) 0.608(2) 0.458(5) 0.051(8) Uiso 1 1 d . . . Na1A Na 0.7500 0.2500 0.9601(10) 0.035(3) Uani 0.25 2 d SP . . Na1B Na 0.7500 0.2500 0.868(2) 0.070(4) Uani 0.25 2 d SP . . O4A O 0.7541(6) 0.3892(7) 1.117(3) 0.063(5) Uani 0.25 1 d P . . O4B O 0.7638(9) 0.3972(7) 1.008(5) 0.032(5) Uani 0.25 1 d P . . H4A H 0.752(2) 0.407(3) 1.013(7) 0.000(9) Uiso 1 1 d . . . H4B H 0.766(2) 0.404(3) 1.061(6) 0.000(10) Uiso 1 1 d . . . O4C O 0.7663(12) 0.4100(11) 0.957(3) 0.040(4) Uani 0.25 1 d P . . O5 O 0.7769(8) 0.3379(18) 0.558(2) 0.187(12) Uani 0.25 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 Bi1 0.01186(3) 0.01186(3) 0.00979(3) 0.000 0.000 0.000 P1 0.01502(12) 0.01463(12) 0.01463(12) -0.00079(9) 0.00161(9) 0.00187(9) O1 0.0173(4) 0.0201(4) 0.0184(4) -0.0043(3) -0.0019(3) 0.0033(3) O2 0.0220(4) 0.0184(4) 0.0211(4) 0.0016(3) 0.0073(3) 0.0021(3) O3 0.0256(5) 0.0160(4) 0.0237(5) 0.0012(3) 0.0074(4) 0.0017(3) N1 0.0164(4) 0.0168(4) 0.0130(4) -0.0001(3) -0.0007(3) 0.0003(3) C1 0.0198(5) 0.0180(5) 0.0156(5) 0.0031(4) -0.0011(4) 0.0006(4) C2 0.0220(5) 0.0214(5) 0.0123(4) -0.0003(4) -0.0037(4) 0.0004(4) C3 0.0151(4) 0.0196(5) 0.0182(5) -0.0010(4) -0.0007(4) 0.0013(4) Na1A 0.028(3) 0.021(2) 0.058(8) 0.000 0.000 -0.006(2) Na1B 0.040(3) 0.024(3) 0.146(12) 0.000 0.000 0.001(2) O4A 0.018(3) 0.022(4) 0.150(15) -0.022(6) 0.001(6) 0.003(2) O4B 0.010(3) 0.005(3) 0.082(16) -0.001(6) -0.010(5) 0.002(2) O4C 0.030(5) 0.017(5) 0.073(9) 0.015(4) 0.008(4) 0.008(3) O5 0.051(6) 0.39(3) 0.120(13) 0.155(19) 0.013(7) 0.054(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 O1 2.4481(9) 4_565 ? Bi1 O1 2.4481(9) . ? Bi1 O1 2.4481(9) 2_665 ? Bi1 O1 2.4481(10) 3_655 ? Bi1 N1 2.6261(11) 3_655 ? Bi1 N1 2.6261(11) 4_565 ? Bi1 N1 2.6261(11) 2_665 ? Bi1 N1 2.6261(11) . ? P1 O1 1.5094(10) . ? P1 O2 1.5152(11) . ? P1 O3 1.5747(11) . ? P1 C3 1.8265(13) . ? O3 H3C 2.23(15) . ? O3 H3D 0.99(5) . ? N1 C3 1.4830(17) . ? N1 C1 1.4898(16) . ? N1 C2 1.4899(17) . ? C1 C2 1.5091(19) 4_565 ? C1 H1A 1.03(2) . ? C1 H1B 1.00(2) . ? C2 C1 1.5091(19) 3_655 ? C2 H2A 0.94(3) . ? C2 H2B 1.01(3) . ? C3 H3A 0.91(2) . ? C3 H3B 0.96(3) . ? Na1A Na1A 0.550(13) 7_667 ? Na1A Na1B 0.637(14) . ? Na1A Na1B 1.186(17) 7_667 ? Na1A O4A 2.118(11) 8_657 ? Na1A O4A 2.118(11) 7_667 ? Na1A O4B 2.187(12) 7_667 ? Na1A O4B 2.187(12) 8_657 ? Na1A O4B 2.201(10) . ? Na1A O4B 2.201(10) 2_655 ? Na1A O4A 2.318(13) . ? Na1A O4A 2.318(13) 2_655 ? Na1A O4C 2.367(16) 2_655 ? Na1A H4A 2.35(4) . ? Na1A H4B 2.39(4) . ? Na1B Na1A 1.186(17) 7_667 ? Na1B Na1B 1.82(3) 7_667 ? Na1B O4A 2.053(11) 7_667 ? Na1B O4A 2.053(11) 8_657 ? Na1B O4B 2.337(19) 7_667 ? Na1B O4B 2.337(19) 8_657 ? Na1B O4B 2.382(16) . ? Na1B O4B 2.382(16) 2_655 ? Na1B O4C 2.446(19) . ? Na1B O4C 2.446(19) 2_655 ? Na1B O5 2.525(18) 2_655 ? Na1B H4A 2.52(4) . ? Na1B H4B 2.64(4) . ? O4A O4B 0.77(4) . ? O4A O4C 1.16(2) . ? O4A Na1B 2.053(11) 7_667 ? O4A Na1A 2.118(11) 7_667 ? O4A H4A 0.76(6) . ? O4A H4B 0.48(5) . ? O4B Na1A 2.187(12) 7_667 ? O4B Na1B 2.337(19) 7_667 ? O4B H4A 0.23(3) . ? O4B H4B 0.38(5) . ? O4C Na1A 2.435(13) 7_667 ? O4C Na1B 2.657(13) 7_667 ? O4C H4A 0.44(4) . ? O4C H4B 0.72(5) . ? 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 Bi1 O1 77.27(2) 4_565 . ? O1 Bi1 O1 77.27(2) 4_565 2_665 ? O1 Bi1 O1 124.01(5) . 2_665 ? O1 Bi1 O1 124.01(5) 4_565 3_655 ? O1 Bi1 O1 77.27(2) . 3_655 ? O1 Bi1 O1 77.27(2) 2_665 3_655 ? O1 Bi1 N1 154.83(3) 4_565 3_655 ? O1 Bi1 N1 127.89(3) . 3_655 ? O1 Bi1 N1 86.74(3) 2_665 3_655 ? O1 Bi1 N1 69.64(3) 3_655 3_655 ? O1 Bi1 N1 69.64(3) 4_565 4_565 ? O1 Bi1 N1 86.74(3) . 4_565 ? O1 Bi1 N1 127.89(3) 2_665 4_565 ? O1 Bi1 N1 154.83(3) 3_655 4_565 ? N1 Bi1 N1 107.19(5) 3_655 4_565 ? O1 Bi1 N1 86.74(3) 4_565 2_665 ? O1 Bi1 N1 154.83(3) . 2_665 ? O1 Bi1 N1 69.64(3) 2_665 2_665 ? O1 Bi1 N1 127.89(3) 3_655 2_665 ? N1 Bi1 N1 69.37(2) 3_655 2_665 ? N1 Bi1 N1 69.37(2) 4_565 2_665 ? O1 Bi1 N1 127.89(3) 4_565 . ? O1 Bi1 N1 69.64(3) . . ? O1 Bi1 N1 154.83(3) 2_665 . ? O1 Bi1 N1 86.74(3) 3_655 . ? N1 Bi1 N1 69.37(2) 3_655 . ? N1 Bi1 N1 69.37(2) 4_565 . ? N1 Bi1 N1 107.19(5) 2_665 . ? O1 P1 O2 117.36(6) . . ? O1 P1 O3 109.11(6) . . ? O2 P1 O3 108.82(6) . . ? O1 P1 C3 106.64(6) . . ? O2 P1 C3 107.19(6) . . ? O3 P1 C3 107.26(6) . . ? P1 O1 Bi1 122.09(5) . . ? P1 O3 H3C 114(4) . . ? P1 O3 H3D 118(3) . . ? H3C O3 H3D 25(5) . . ? C3 N1 C1 109.16(10) . . ? C3 N1 C2 110.13(10) . . ? C1 N1 C2 110.26(10) . . ? C3 N1 Bi1 107.24(7) . . ? C1 N1 Bi1 109.61(7) . . ? C2 N1 Bi1 110.38(7) . . ? N1 C1 C2 112.61(11) . 4_565 ? N1 C1 H1A 110.5(15) . . ? C2 C1 H1A 107.3(14) 4_565 . ? N1 C1 H1B 107.9(13) . . ? C2 C1 H1B 107.9(12) 4_565 . ? H1A C1 H1B 110.6(19) . . ? N1 C2 C1 112.52(10) . 3_655 ? N1 C2 H2A 108.0(18) . . ? C1 C2 H2A 107.6(19) 3_655 . ? N1 C2 H2B 109.6(15) . . ? C1 C2 H2B 108.8(16) 3_655 . ? H2A C2 H2B 110(2) . . ? N1 C3 P1 112.74(8) . . ? N1 C3 H3A 113.5(16) . . ? P1 C3 H3A 104.4(17) . . ? N1 C3 H3B 111(2) . . ? P1 C3 H3B 107(2) . . ? H3A C3 H3B 108(2) . . ? Na1A Na1A Na1B 180.000(19) 7_667 . ? Na1A Na1A Na1B 0.000(5) 7_667 7_667 ? Na1B Na1A Na1B 180.000(5) . 7_667 ? Na1A Na1A O4A 104.6(6) 7_667 8_657 ? Na1B Na1A O4A 75.4(6) . 8_657 ? Na1B Na1A O4A 104.6(6) 7_667 8_657 ? Na1A Na1A O4A 104.6(6) 7_667 7_667 ? Na1B Na1A O4A 75.4(6) . 7_667 ? Na1B Na1A O4A 104.6(6) 7_667 7_667 ? O4A Na1A O4A 150.9(12) 8_657 7_667 ? Na1A Na1A O4B 84.3(10) 7_667 7_667 ? Na1B Na1A O4B 95.7(10) . 7_667 ? Na1B Na1A O4B 84.3(10) 7_667 7_667 ? O4A Na1A O4B 170.4(11) 8_657 7_667 ? O4A Na1A O4B 20.6(10) 7_667 7_667 ? Na1A Na1A O4B 84.3(10) 7_667 8_657 ? Na1B Na1A O4B 95.7(10) . 8_657 ? Na1B Na1A O4B 84.3(10) 7_667 8_657 ? O4A Na1A O4B 20.6(10) 8_657 8_657 ? O4A Na1A O4B 170.4(11) 7_667 8_657 ? O4B Na1A O4B 168.6(19) 7_667 8_657 ? Na1A Na1A O4B 81.3(10) 7_667 . ? Na1B Na1A O4B 98.7(10) . . ? Na1B Na1A O4B 81.3(10) 7_667 . ? O4A Na1A O4B 95.7(4) 8_657 . ? O4A Na1A O4B 88.6(6) 7_667 . ? O4B Na1A O4B 89.14(6) 7_667 . ? O4B Na1A O4B 89.14(7) 8_657 . ? Na1A Na1A O4B 81.3(10) 7_667 2_655 ? Na1B Na1A O4B 98.7(10) . 2_655 ? Na1B Na1A O4B 81.3(10) 7_667 2_655 ? O4A Na1A O4B 88.6(6) 8_657 2_655 ? O4A Na1A O4B 95.7(4) 7_667 2_655 ? O4B Na1A O4B 89.14(7) 7_667 2_655 ? O4B Na1A O4B 89.14(6) 8_657 2_655 ? O4B Na1A O4B 162.6(19) . 2_655 ? Na1A Na1A O4A 62.2(5) 7_667 . ? Na1B Na1A O4A 117.8(5) . . ? Na1B Na1A O4A 62.2(5) 7_667 . ? O4A Na1A O4A 96.7(4) 8_657 . ? O4A Na1A O4A 96.7(4) 7_667 . ? O4B Na1A O4A 90.6(5) 7_667 . ? O4B Na1A O4A 84.1(7) 8_657 . ? O4B Na1A O4A 19.4(10) . . ? O4B Na1A O4A 143.3(12) 2_655 . ? Na1A Na1A O4A 62.2(5) 7_667 2_655 ? Na1B Na1A O4A 117.8(5) . 2_655 ? Na1B Na1A O4A 62.2(5) 7_667 2_655 ? O4A Na1A O4A 96.7(4) 8_657 2_655 ? O4A Na1A O4A 96.7(4) 7_667 2_655 ? O4B Na1A O4A 84.1(7) 7_667 2_655 ? O4B Na1A O4A 90.6(5) 8_657 2_655 ? O4B Na1A O4A 143.3(12) . 2_655 ? O4B Na1A O4A 19.4(10) 2_655 2_655 ? O4A Na1A O4A 124.3(10) . 2_655 ? Na1A Na1A O4C 90.5(5) 7_667 2_655 ? Na1B Na1A O4C 89.5(5) . 2_655 ? Na1B Na1A O4C 90.5(5) 7_667 2_655 ? O4A Na1A O4C 85.9(6) 8_657 2_655 ? O4A Na1A O4C 93.9(5) 7_667 2_655 ? O4B Na1A O4C 90.5(7) 7_667 2_655 ? O4B Na1A O4C 89.6(7) 8_657 2_655 ? O4B Na1A O4C 171.8(10) . 2_655 ? O4B Na1A O4C 9.2(12) 2_655 2_655 ? O4A Na1A O4C 152.4(8) . 2_655 ? O4A Na1A O4C 28.6(6) 2_655 2_655 ? Na1A Na1A H4A 81.0(12) 7_667 . ? Na1B Na1A H4A 99.0(12) . . ? Na1B Na1A H4A 81.0(12) 7_667 . ? O4A Na1A H4A 91.3(9) 8_657 . ? O4A Na1A H4A 93.2(9) 7_667 . ? O4B Na1A H4A 93.7(8) 7_667 . ? O4B Na1A H4A 84.5(9) 8_657 . ? O4B Na1A H4A 4.7(9) . . ? O4B Na1A H4A 161.7(9) 2_655 . ? O4A Na1A H4A 18.8(14) . . ? O4A Na1A H4A 143.1(12) 2_655 . ? O4C Na1A H4A 170.0(12) 2_655 . ? Na1A Na1A H4B 73.0(10) 7_667 . ? Na1B Na1A H4B 107.0(10) . . ? Na1B Na1A H4B 73.0(10) 7_667 . ? O4A Na1A H4B 98.0(9) 8_657 . ? O4A Na1A H4B 90.4(9) 7_667 . ? O4B Na1A H4B 88.0(10) 7_667 . ? O4B Na1A H4B 88.7(10) 8_657 . ? O4B Na1A H4B 8.3(16) . . ? O4B Na1A H4B 154.3(12) 2_655 . ? O4A Na1A H4B 11.5(12) . . ? O4A Na1A H4B 135.0(11) 2_655 . ? O4C Na1A H4B 163.5(11) 2_655 . ? H4A Na1A H4B 9.4(13) . . ? Na1A Na1B Na1A 0.000(5) . 7_667 ? Na1A Na1B Na1B 0.000(6) . 7_667 ? Na1A Na1B Na1B 0.000(2) 7_667 7_667 ? Na1A Na1B O4A 87.1(7) . 7_667 ? Na1A Na1B O4A 87.1(7) 7_667 7_667 ? Na1B Na1B O4A 87.1(7) 7_667 7_667 ? Na1A Na1B O4A 87.1(7) . 8_657 ? Na1A Na1B O4A 87.1(7) 7_667 8_657 ? Na1B Na1B O4A 87.1(7) 7_667 8_657 ? O4A Na1B O4A 174.2(14) 7_667 8_657 ? Na1A Na1B O4B 68.6(9) . 7_667 ? Na1A Na1B O4B 68.6(9) 7_667 7_667 ? Na1B Na1B O4B 68.6(9) 7_667 7_667 ? O4A Na1B O4B 18.9(10) 7_667 7_667 ? O4A Na1B O4B 155.4(12) 8_657 7_667 ? Na1A Na1B O4B 68.6(9) . 8_657 ? Na1A Na1B O4B 68.6(9) 7_667 8_657 ? Na1B Na1B O4B 68.6(9) 7_667 8_657 ? O4A Na1B O4B 155.4(12) 7_667 8_657 ? O4A Na1B O4B 18.9(10) 8_657 8_657 ? O4B Na1B O4B 137.2(17) 7_667 8_657 ? Na1A Na1B O4B 66.0(9) . . ? Na1A Na1B O4B 66.0(9) 7_667 . ? Na1B Na1B O4B 66.0(9) 7_667 . ? O4A Na1B O4B 85.4(5) 7_667 . ? O4A Na1B O4B 92.2(5) 8_657 . ? O4B Na1B O4B 81.5(2) 7_667 . ? O4B Na1B O4B 81.5(2) 8_657 . ? Na1A Na1B O4B 66.0(9) . 2_655 ? Na1A Na1B O4B 66.0(9) 7_667 2_655 ? Na1B Na1B O4B 66.0(9) 7_667 2_655 ? O4A Na1B O4B 92.2(5) 7_667 2_655 ? O4A Na1B O4B 85.4(5) 8_657 2_655 ? O4B Na1B O4B 81.5(2) 7_667 2_655 ? O4B Na1B O4B 81.5(2) 8_657 2_655 ? O4B Na1B O4B 132.0(18) . 2_655 ? Na1A Na1B O4C 75.4(5) . . ? Na1A Na1B O4C 75.4(5) 7_667 . ? Na1B Na1B O4C 75.4(5) 7_667 . ? O4A Na1B O4C 85.3(6) 7_667 . ? O4A Na1B O4C 93.3(6) 8_657 . ? O4B Na1B O4C 84.3(6) 7_667 . ? O4B Na1B O4C 85.1(8) 8_657 . ? O4B Na1B O4C 9.4(10) . . ? O4B Na1B O4C 141.4(11) 2_655 . ? Na1A Na1B O4C 75.4(5) . 2_655 ? Na1A Na1B O4C 75.4(5) 7_667 2_655 ? Na1B Na1B O4C 75.4(5) 7_667 2_655 ? O4A Na1B O4C 93.3(6) 7_667 2_655 ? O4A Na1B O4C 85.3(6) 8_657 2_655 ? O4B Na1B O4C 85.1(8) 7_667 2_655 ? O4B Na1B O4C 84.3(6) 8_657 2_655 ? O4B Na1B O4C 141.4(11) . 2_655 ? O4B Na1B O4C 9.4(10) 2_655 2_655 ? O4C Na1B O4C 150.8(10) . 2_655 ? Na1A Na1B O5 147.6(7) . 2_655 ? Na1A Na1B O5 147.6(7) 7_667 2_655 ? Na1B Na1B O5 147.6(7) 7_667 2_655 ? O4A Na1B O5 100.6(7) 7_667 2_655 ? O4A Na1B O5 84.3(6) 8_657 2_655 ? O4B Na1B O5 114.2(7) 7_667 2_655 ? O4B Na1B O5 102.0(8) 8_657 2_655 ? O4B Na1B O5 145.4(12) . 2_655 ? O4B Na1B O5 82.2(11) 2_655 2_655 ? O4C Na1B O5 136.2(9) . 2_655 ? O4C Na1B O5 72.8(8) 2_655 2_655 ? Na1A Na1B H4A 66.6(12) . . ? Na1A Na1B H4A 66.6(12) 7_667 . ? Na1B Na1B H4A 66.6(12) 7_667 . ? O4A Na1B H4A 89.8(8) 7_667 . ? O4A Na1B H4A 87.9(8) 8_657 . ? O4B Na1B H4A 85.7(9) 7_667 . ? O4B Na1B H4A 77.6(10) 8_657 . ? O4B Na1B H4A 4.3(7) . . ? O4B Na1B H4A 132.3(11) 2_655 . ? O4C Na1B H4A 10.1(10) . . ? O4C Na1B H4A 141.6(14) 2_655 . ? O5 Na1B H4A 143.9(14) 2_655 . ? Na1A Na1B H4B 59.7(10) . . ? Na1A Na1B H4B 59.7(10) 7_667 . ? Na1B Na1B H4B 59.7(10) 7_667 . ? O4A Na1B H4B 85.0(9) 7_667 . ? O4A Na1B H4B 92.0(9) 8_657 . ? O4B Na1B H4B 79.1(10) 7_667 . ? O4B Na1B H4B 79.7(11) 8_657 . ? O4B Na1B H4B 6.3(15) . . ? O4B Na1B H4B 125.7(11) 2_655 . ? O4C Na1B H4B 15.7(11) . . ? O4C Na1B H4B 135.1(11) 2_655 . ? O5 Na1B H4B 151.6(12) 2_655 . ? H4A Na1B H4B 8.2(13) . . ? O4B O4A O4C 6.8(16) . . ? O4B O4A Na1B 101.9(15) . 7_667 ? O4C O4A Na1B 108.5(14) . 7_667 ? O4B O4A Na1A 84.7(14) . 7_667 ? O4C O4A Na1A 91.2(13) . 7_667 ? Na1B O4A Na1A 17.5(4) 7_667 7_667 ? O4B O4A Na1A 71.7(14) . . ? O4C O4A Na1A 78.1(12) . . ? Na1B O4A Na1A 30.7(5) 7_667 . ? Na1A O4A Na1A 13.3(3) 7_667 . ? O4B O4A Na1B 59.8(13) . . ? O4C O4A Na1B 66.1(12) . . ? Na1B O4A Na1B 42.9(7) 7_667 . ? Na1A O4A Na1B 25.4(4) 7_667 . ? Na1A O4A Na1B 12.2(3) . . ? O4B O4A H4A 18(3) . . ? O4C O4A H4A 12(3) . . ? Na1B O4A H4A 113(3) 7_667 . ? Na1A O4A H4A 96(3) 7_667 . ? Na1A O4A H4A 83(3) . . ? Na1B O4A H4A 70(3) . . ? O4B O4A H4B 23(4) . . ? O4C O4A H4B 18(5) . . ? Na1B O4A H4B 121(6) 7_667 . ? Na1A O4A H4B 105(5) 7_667 . ? Na1A O4A H4B 92(5) . . ? Na1B O4A H4B 81(5) . . ? H4A O4A H4B 25(5) . . ? O4A O4B Na1A 74.7(12) . 7_667 ? O4A O4B Na1A 88.9(12) . . ? Na1A O4B Na1A 14.4(4) 7_667 . ? O4A O4B Na1B 59.2(11) . 7_667 ? Na1A O4B Na1B 15.7(4) 7_667 7_667 ? Na1A O4B Na1B 30.1(5) . 7_667 ? O4A O4B Na1B 104.0(12) . . ? Na1A O4B Na1B 29.7(4) 7_667 . ? Na1A O4B Na1B 15.3(3) . . ? Na1B O4B Na1B 45.4(7) 7_667 . ? O4A O4B H4A 79(10) . . ? Na1A O4B H4A 123(10) 7_667 . ? Na1A O4B H4A 126(10) . . ? Na1B O4B H4A 118(10) 7_667 . ? Na1B O4B H4A 125(10) . . ? O4A O4B H4B 29(8) . . ? Na1A O4B H4B 101(9) 7_667 . ? Na1A O4B H4B 115(9) . . ? Na1B O4B H4B 85(9) 7_667 . ? Na1B O4B H4B 130(9) . . ? H4A O4B H4B 74(10) . . ? O4A O4C Na1A 73.3(9) . . ? O4A O4C Na1A 60.4(9) . 7_667 ? Na1A O4C Na1A 13.0(3) . 7_667 ? O4A O4C Na1B 88.3(11) . . ? Na1A O4C Na1B 15.1(3) . . ? Na1A O4C Na1B 28.1(4) 7_667 . ? O4A O4C Na1B 47.1(9) . 7_667 ? Na1A O4C Na1B 26.5(4) . 7_667 ? Na1A O4C Na1B 13.5(3) 7_667 7_667 ? Na1B O4C Na1B 41.6(6) . 7_667 ? O4A O4C H4A 22(6) . . ? Na1A O4C H4A 82(6) . . ? Na1A O4C H4A 70(6) 7_667 . ? Na1B O4C H4A 95(6) . . ? Na1B O4C H4A 59(7) 7_667 . ? O4A O4C H4B 12(3) . . ? Na1A O4C H4B 83(4) . . ? Na1A O4C H4B 70(4) 7_667 . ? Na1B O4C H4B 98(4) . . ? Na1B O4C H4B 56(4) 7_667 . ? H4A O4C H4B 28(6) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 40.28 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.210 _refine_diff_density_min -2.284 _refine_diff_density_rms 0.106 data_BiDOTMPOx _database_code_CSD 191714 _audit_creation_date ? _audit_creation_method ? _audit_update_record ? _publ_section_abstract ? _publ_section_comment ? _publ_section_acknowledgements ? _publ_section_references ? _publ_section_figure_captions ? _publ_section_exptl_prep ? _publ_section_exptl_refinement ? _refine_ls_shift/esd_max 1.05 _refine_ls_shift/esd_mean 0.18 _computing_structure_refinement GSAS _refine_ls_number_parameters 66 _refine_ls_goodness_of_fit_all 2.10 _refine_ls_number_restraints 8 _pd_proc_ls_prof_R_factor 0.0369 _pd_proc_ls_prof_wR_factor 0.0484 _pd_proc_ls_prof_F2_factor 0.0501 _cell_length_a 13.24204(8) _cell_length_b 13.24204 _cell_length_c 6.89488(6) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_volume 1209.02(2) _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 2.170 _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 4/n' loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -y+1/2,+x,+z -x+1/2,-y+1/2,+z +y,-x+1/2,+z -x,-y,-z +y+1/2,-x,-z +x+1/2,+y+1/2,-z -y,+x+1/2,-z loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_thermal_displace_type _atom_site_U_iso_or_equiv _atom_site_symmetry_multiplicity BI 0.25 0.25 0.80416(11) 1.0 Uiso 0.0107(4) 2 P 0.50438(22) 0.20745(22) 0.9150(4) 1.0 Uiso 0.0212(12) 8 O1 0.4108(4) 0.2667(5) 0.9746(7) 1.0 Uiso 0.0074(13) 8 O2 0.5907(4) 0.2798(4) 0.8741(8) 1.0 Uiso 0.0074(13) 8 O3 0.6288(4) 0.4633(5) 0.9348(8) 1.0 Uiso 0.0074(13) 8 N 0.4073(5) 0.1943(4) 0.5569(10) 1.0 Uiso 0.0051(16) 8 C1 0.3611(6) 0.1254(6) 0.4127(9) 1.0 Uiso 0.0051(16) 8 C3 0.4713(6) 0.1370(5) 0.6954(8) 1.0 Uiso 0.0051(16) 8 C2 0.2878(4) 0.0438(6) 0.4795(12) 1.0 Uiso 0.0051(16) 8 O4 0.75 0.25 0.6743(14) 1.0 Uiso 0.0657(31) 4 loop_ _atom_type_symbol _atom_type_number_in_cell BI 2.0 P 8.0 O 28.0 N 8.0 C 24.0 _chemical_formula_sum 'C 12 H 33 N 4 Bi 1 O 14 P 4' _chemical_formula_weight 790.28 _diffrn_ambient_temperature 298 _diffrn_ambient_environment 'air' _diffrn_ambient_pressure '1 atm' _diffrn_radiation_source Cu _diffrn_radiation_detector 'Braun linear PSD' _pd_instr_radiation_probe x-ray _diffrn_radiation_polarisn_ratio 0.83 _diffrn_radiation_wavelength 1.540598 _diffrn_radiation_type 'Cu K\a~1~' _pd_proc_info_datetime 'Aug 14 09:01:31 2001' _pd_calc_method 'Rietveld Refinement' _pd_meas_2theta_range_min 8.000 _pd_meas_2theta_range_max 89.72576 _pd_meas_2theta_range_inc 0.0155517 _pd_proc_2theta_range_min 8.0000 _pd_proc_2theta_range_max 89.72576 _pd_proc_2theta_range_inc 0.0155517 _reflns_number_observed 513 _reflns_limit_h_min 0 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 6 _reflns_d_resolution_high 1.095 _reflns_d_resolution_low 9.364 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance BI O1 2.443(5) BI O1 2.443(5) BI O1 2.443(5) BI O1 2.443(5) BI N 2.791(6) BI N 2.791(6) BI N 2.791(6) BI N 2.791(6) P O1 1.5226(34) P O2 1.5176(32) P O3 1.530(7) P C3 1.8312(25) N BI 2.791(6) N C1 1.4814(26) N C3 1.4853(26) N C2 1.496(10) C1 N 1.4814(26) C1 C2 1.5231(26) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O1 BI O1 76.61(10) O1 BI O1 122.47(23) O1 BI O1 76.61(10) O1 BI O1 76.61(10) O1 BI O1 122.47(23) O1 BI O1 76.61(10) O1 P O2 109.8(4) O1 P O3 113.3(4) O1 P C3 106.9(4) O2 P O3 110.2(4) O2 P C3 110.4(4) O3 P C3 106.3(4) BI O1 P 122.20(34) C1 N C3 110.6(5) C1 N C2 116.7(7) C3 N C2 113.9(8) N C1 C2 119.8(7) P C3 N 114.1(5) N C2 C1 109.1(7) N Bi N 104.7(5) N Bi N 68.1(2)