# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2010 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Murugavel, Ramaswamy' _publ_contact_author_email rmv@chem.iitb.ac.in _publ_section_title ; One, Two, and Three Methylene Phosphonic Acid Groups (CH2PO3H2) on a Mesitylene Ring: Synthesis, Chracterization and Aspects of of Supramolecular Aggregation ; _publ_author_name R.Murugavel # Attachment '- murugavel_phosphonic.cif' data_newrm237 _database_code_depnum_ccdc_archive 'CCDC 755660' #TrackingRef '- murugavel_phosphonic.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H15 O3 P' _chemical_formula_weight 214.19 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 monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.055(4) _cell_length_b 4.6342(11) _cell_length_c 16.179(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.38(2) _cell_angle_gamma 90.00 _cell_volume 1049.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 863 _cell_measurement_theta_min 2.8783 _cell_measurement_theta_max 32.4897 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.241 _exptl_absorpt_correction_T_min 0.62785 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTIOM X CALIBUR-S' _diffrn_measurement_method 'omega(w)-q scan' _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8445 _diffrn_reflns_av_R_equivalents 0.2024 _diffrn_reflns_av_sigmaI/netI 0.2540 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1851 _reflns_number_gt 615 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0436P)^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 1851 _refine_ls_number_parameters 130 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1591 _refine_ls_R_factor_gt 0.0566 _refine_ls_wR_factor_ref 0.1255 _refine_ls_wR_factor_gt 0.1112 _refine_ls_goodness_of_fit_ref 0.673 _refine_ls_restrained_S_all 0.673 _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 0.87190(10) 0.1365(3) 0.79174(9) 0.0390(4) Uani 1 1 d . . . O2 O 0.9593(2) 0.2804(7) 0.8411(2) 0.0442(10) Uani 1 1 d . . . O1 O 0.8960(2) -0.1150(7) 0.73955(18) 0.0400(9) Uani 1 1 d . . . O3 O 0.8201(2) 0.3742(7) 0.73700(18) 0.0414(9) Uani 1 1 d . . . C1 C 0.7518(4) 0.2446(10) 0.9183(3) 0.0327(13) Uani 1 1 d . . . C2 C 0.6617(4) 0.3653(12) 0.8912(3) 0.0383(13) Uani 1 1 d . . . C3 C 0.6209(4) 0.5662(11) 0.9425(3) 0.0405(15) Uani 1 1 d . . . H3 H 0.5606 0.6475 0.9240 0.049 Uiso 1 1 calc R . . C4 C 0.6642(4) 0.6497(11) 1.0178(3) 0.0410(14) Uani 1 1 d . . . C5 C 0.7537(4) 0.5320(11) 1.0427(3) 0.0420(15) Uani 1 1 d . . . H5 H 0.7862 0.5886 1.0943 0.050 Uiso 1 1 calc R . . C6 C 0.7961(4) 0.3334(11) 0.9933(3) 0.0371(13) Uani 1 1 d . . . C7 C 0.6077(4) 0.2740(12) 0.8104(3) 0.0558(18) Uani 1 1 d . . . H7A H 0.6461 0.3165 0.7644 0.084 Uiso 1 1 calc R . . H7B H 0.5471 0.3797 0.8025 0.084 Uiso 1 1 calc R . . H7C H 0.5947 0.0663 0.8119 0.084 Uiso 1 1 calc R . . C8 C 0.6184(4) 0.8579(11) 1.0721(3) 0.0539(16) Uani 1 1 d . . . H8A H 0.6309 1.0554 1.0544 0.081 Uiso 1 1 calc R . . H8B H 0.6449 0.8313 1.1298 0.081 Uiso 1 1 calc R . . H8C H 0.5493 0.8238 1.0677 0.081 Uiso 1 1 calc R . . C9 C 0.8916(3) 0.2079(11) 1.0280(3) 0.0461(16) Uani 1 1 d . . . H9A H 0.8867 -0.0028 1.0306 0.069 Uiso 1 1 calc R . . H9B H 0.9087 0.2845 1.0839 0.069 Uiso 1 1 calc R . . H9C H 0.9410 0.2612 0.9918 0.069 Uiso 1 1 calc R . . C10 C 0.7966(3) 0.0217(11) 0.8658(3) 0.0379(14) Uani 1 1 d . . . H10A H 0.7441 -0.0912 0.8363 0.045 Uiso 1 1 calc R . . H10B H 0.8336 -0.1127 0.9039 0.045 Uiso 1 1 calc R . . H2W H 1.0112 0.2157 0.8215 0.080 Uiso 1 1 d . . . H3W H 0.8591 0.5189 0.7325 0.080 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0380(9) 0.0393(9) 0.0398(8) 0.0020(9) 0.0043(7) -0.0003(9) O2 0.038(2) 0.051(2) 0.044(2) -0.0015(17) 0.0087(17) -0.0051(18) O1 0.049(2) 0.034(2) 0.039(2) 0.0002(19) 0.0128(16) 0.0080(19) O3 0.040(2) 0.041(2) 0.043(2) 0.006(2) 0.0002(16) 0.000(2) C1 0.041(4) 0.027(3) 0.030(3) -0.008(2) 0.007(3) -0.005(3) C2 0.035(3) 0.046(3) 0.034(3) 0.003(3) 0.001(3) -0.001(3) C3 0.029(3) 0.043(4) 0.049(4) 0.003(3) 0.003(3) 0.005(3) C4 0.052(4) 0.036(3) 0.037(3) -0.009(3) 0.016(3) 0.003(3) C5 0.045(4) 0.045(4) 0.036(3) -0.004(3) 0.002(3) -0.007(3) C6 0.048(4) 0.034(3) 0.031(3) -0.001(3) 0.011(3) 0.002(3) C7 0.051(4) 0.073(4) 0.043(4) 0.008(3) 0.003(3) -0.001(3) C8 0.053(4) 0.052(4) 0.058(4) -0.005(4) 0.010(3) 0.012(4) C9 0.039(4) 0.057(4) 0.042(3) 0.005(3) 0.002(3) 0.006(3) C10 0.030(3) 0.039(3) 0.043(3) 0.001(3) -0.003(3) 0.005(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 O1 1.496(3) . ? P1 O2 1.551(4) . ? P1 O3 1.552(3) . ? P1 C10 1.754(4) . ? O2 H2W 0.875 . ? O3 H3W 0.874 . ? C1 C6 1.374(6) . ? C1 C2 1.416(6) . ? C1 C10 1.512(6) . ? C2 C3 1.405(6) . ? C2 C7 1.509(7) . ? C3 C4 1.366(6) . ? C3 H3 0.9500 . ? C4 C5 1.395(6) . ? C4 C8 1.490(6) . ? C5 C6 1.390(6) . ? C5 H5 0.9500 . ? C6 C9 1.521(6) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? 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 P1 O2 114.54(19) . . ? O1 P1 O3 110.46(19) . . ? O2 P1 O3 107.15(19) . . ? O1 P1 C10 109.4(2) . . ? O2 P1 C10 106.2(2) . . ? O3 P1 C10 108.9(2) . . ? P1 O2 H2W 108.2 . . ? P1 O3 H3W 109.2 . . ? C6 C1 C2 118.2(4) . . ? C6 C1 C10 121.5(5) . . ? C2 C1 C10 120.2(5) . . ? C3 C2 C1 118.8(5) . . ? C3 C2 C7 119.8(5) . . ? C1 C2 C7 121.3(5) . . ? C4 C3 C2 122.8(5) . . ? C4 C3 H3 118.6 . . ? C2 C3 H3 118.6 . . ? C3 C4 C5 117.5(5) . . ? C3 C4 C8 121.8(5) . . ? C5 C4 C8 120.7(5) . . ? C6 C5 C4 121.1(5) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C1 C6 C5 121.6(5) . . ? C1 C6 C9 121.5(5) . . ? C5 C6 C9 116.9(5) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C1 C10 P1 119.1(4) . . ? C1 C10 H10A 107.5 . . ? P1 C10 H10A 107.5 . . ? C1 C10 H10B 107.5 . . ? P1 C10 H10B 107.5 . . ? H10A C10 H10B 107.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.0(7) . . . . ? C10 C1 C2 C3 178.4(4) . . . . ? C6 C1 C2 C7 -178.7(5) . . . . ? C10 C1 C2 C7 0.7(7) . . . . ? C1 C2 C3 C4 -0.3(7) . . . . ? C7 C2 C3 C4 177.4(5) . . . . ? C2 C3 C4 C5 1.4(7) . . . . ? C2 C3 C4 C8 -178.5(5) . . . . ? C3 C4 C5 C6 -1.1(7) . . . . ? C8 C4 C5 C6 178.7(4) . . . . ? C2 C1 C6 C5 1.3(7) . . . . ? C10 C1 C6 C5 -178.1(4) . . . . ? C2 C1 C6 C9 178.2(4) . . . . ? C10 C1 C6 C9 -1.2(7) . . . . ? C4 C5 C6 C1 -0.2(7) . . . . ? C4 C5 C6 C9 -177.3(5) . . . . ? C6 C1 C10 P1 -90.4(5) . . . . ? C2 C1 C10 P1 90.3(5) . . . . ? O1 P1 C10 C1 -171.9(4) . . . . ? O2 P1 C10 C1 64.1(4) . . . . ? O3 P1 C10 C1 -51.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.310 _refine_diff_density_min -0.312 _refine_diff_density_rms 0.074 data_newrm265 _database_code_depnum_ccdc_archive 'CCDC 755661' #TrackingRef '- murugavel_phosphonic.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H24 O7 P2' _chemical_formula_weight 354.26 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 13.687(5) _cell_length_b 21.666(5) _cell_length_c 7.258(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2152.3(18) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1464 _cell_measurement_theta_min 2.9457 _cell_measurement_theta_max 32.4859 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.093 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.225 _exptl_absorpt_correction_T_min 0.18105 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTIOM X CALIBUR-S' _diffrn_measurement_method 'omega(w)-q scan' _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17950 _diffrn_reflns_av_R_equivalents 0.1083 _diffrn_reflns_av_sigmaI/netI 0.1836 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3768 _reflns_number_gt 1232 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1602P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.4(3) _refine_ls_number_reflns 3768 _refine_ls_number_parameters 205 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1886 _refine_ls_R_factor_gt 0.0977 _refine_ls_wR_factor_ref 0.2652 _refine_ls_wR_factor_gt 0.2464 _refine_ls_goodness_of_fit_ref 0.756 _refine_ls_restrained_S_all 0.756 _refine_ls_shift/su_max 0.067 _refine_ls_shift/su_mean 0.012 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 -0.0120(2) 0.79135(14) 0.2768(4) 0.0925(10) Uani 1 1 d . . . P2 P 0.44551(19) 0.82389(12) 0.2621(5) 0.0886(9) Uani 1 1 d . . . O1 O 0.0640(5) 0.7490(3) 0.3556(9) 0.096(2) Uani 1 1 d . . . O2 O -0.0273(5) 0.7826(3) 0.0705(9) 0.097(2) Uani 1 1 d . . . O3 O -0.1096(4) 0.7848(3) 0.3746(9) 0.107(2) Uani 1 1 d . . . O4 O 0.4732(5) 0.8230(3) 0.0638(9) 0.107(2) Uani 1 1 d . . . O5 O 0.5406(4) 0.8250(3) 0.3811(10) 0.104(2) Uani 1 1 d . . . O6 O 0.3796(4) 0.7732(3) 0.3249(9) 0.096(2) Uani 1 1 d . . . C1 C 0.2844(9) 0.9340(4) 0.0483(18) 0.097(3) Uani 1 1 d . . . C2 C 0.1885(9) 0.9404(4) -0.0427(14) 0.081(3) Uani 1 1 d . . . H2A H 0.1850 0.9573 -0.1604 0.097 Uiso 1 1 calc R . . C3 C 0.1087(9) 0.9228(4) 0.0400(15) 0.087(3) Uani 1 1 d . . . C4 C 0.1162(7) 0.8919(4) 0.2203(14) 0.078(3) Uani 1 1 d . . . C5 C 0.2023(7) 0.8861(4) 0.3043(12) 0.073(2) Uani 1 1 d . . . C6 C 0.2883(7) 0.9070(4) 0.2182(14) 0.080(3) Uani 1 1 d . . . C7 C 0.3773(7) 0.9562(5) -0.0630(15) 0.108(3) Uani 1 1 d . . . H7A H 0.3581 0.9866 -0.1523 0.161 Uiso 1 1 calc R . . H7B H 0.4064 0.9216 -0.1247 0.161 Uiso 1 1 calc R . . H7C H 0.4238 0.9740 0.0205 0.161 Uiso 1 1 calc R . . C8 C 0.0097(9) 0.9253(5) -0.0565(16) 0.124(4) Uani 1 1 d . . . H8A H -0.0240 0.8869 -0.0388 0.185 Uiso 1 1 calc R . . H8B H 0.0192 0.9323 -0.1859 0.185 Uiso 1 1 calc R . . H8C H -0.0285 0.9583 -0.0056 0.185 Uiso 1 1 calc R . . C9 C 0.0193(6) 0.8692(5) 0.3136(13) 0.091(3) Uani 1 1 d . . . H9A H -0.0339 0.8947 0.2694 0.109 Uiso 1 1 calc R . . H9B H 0.0248 0.8759 0.4453 0.109 Uiso 1 1 calc R . . C10 C 0.2112(9) 0.8557(5) 0.5052(13) 0.111(4) Uani 1 1 d . . . H10A H 0.2340 0.8862 0.5912 0.167 Uiso 1 1 calc R . . H10B H 0.2566 0.8220 0.5010 0.167 Uiso 1 1 calc R . . H10C H 0.1484 0.8408 0.5436 0.167 Uiso 1 1 calc R . . C11 C 0.3880(7) 0.8976(4) 0.3117(14) 0.090(3) Uani 1 1 d . . . H11A H 0.3795 0.9013 0.4440 0.107 Uiso 1 1 calc R . . H11B H 0.4316 0.9304 0.2727 0.107 Uiso 1 1 calc R . . O7 O 0.2151(8) 0.7628(6) -0.0579(12) 0.194(5) Uani 1 1 d D . . H7 H 0.2512 0.7930 -0.0598 0.291 Uiso 1 1 calc R . . C13 C 0.2253(6) 0.7316(4) 0.1145(11) 0.052(2) Uani 1 1 d D . . H13A H 0.1653 0.7364 0.1841 0.063 Uiso 1 1 calc R . . H13B H 0.2773 0.7510 0.1842 0.063 Uiso 1 1 calc R . . C12 C 0.2473(10) 0.6641(4) 0.096(2) 0.170(6) Uani 1 1 d D . . H12A H 0.2264 0.6499 -0.0229 0.255 Uiso 1 1 calc R . . H12B H 0.2133 0.6416 0.1903 0.255 Uiso 1 1 calc R . . H12C H 0.3164 0.6576 0.1089 0.255 Uiso 1 1 calc 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 P1 0.0797(18) 0.106(2) 0.092(2) 0.0011(18) 0.0130(17) -0.0036(15) P2 0.0850(17) 0.0824(17) 0.098(2) 0.0058(17) -0.0085(17) -0.0076(15) O1 0.079(4) 0.105(5) 0.105(5) 0.013(4) 0.005(4) -0.001(4) O2 0.129(6) 0.094(5) 0.070(4) 0.018(4) 0.001(4) -0.001(4) O3 0.067(4) 0.148(6) 0.105(5) 0.036(4) -0.008(4) -0.005(4) O4 0.134(6) 0.118(5) 0.068(5) 0.014(4) 0.005(4) -0.004(5) O5 0.071(4) 0.109(5) 0.130(6) 0.020(4) -0.031(4) -0.019(4) O6 0.096(4) 0.088(4) 0.104(5) 0.023(4) -0.023(4) -0.023(4) C1 0.103(9) 0.064(7) 0.122(10) 0.017(6) 0.000(8) -0.014(6) C2 0.109(8) 0.067(6) 0.066(6) 0.019(5) 0.021(7) -0.008(6) C3 0.113(9) 0.078(7) 0.072(8) -0.003(5) -0.006(7) 0.018(6) C4 0.085(7) 0.072(6) 0.079(7) 0.002(5) -0.001(6) -0.002(5) C5 0.081(7) 0.077(6) 0.061(6) -0.015(5) -0.017(6) 0.004(5) C6 0.087(7) 0.085(7) 0.070(7) 0.010(6) 0.001(6) -0.019(5) C7 0.108(8) 0.112(8) 0.103(8) 0.029(7) 0.000(7) -0.013(7) C8 0.146(10) 0.125(9) 0.101(8) -0.006(7) -0.055(9) 0.055(8) C9 0.078(6) 0.122(9) 0.074(7) -0.013(6) 0.010(6) 0.026(6) C10 0.134(9) 0.129(9) 0.070(7) -0.005(6) 0.001(7) 0.006(7) C11 0.097(7) 0.086(7) 0.086(7) -0.001(6) -0.026(6) -0.027(5) O7 0.165(10) 0.273(15) 0.143(8) -0.041(10) 0.014(8) -0.008(8) C13 0.056(4) 0.048(5) 0.052(5) 0.000(4) -0.003(4) 0.002(4) C12 0.153(11) 0.157(15) 0.200(16) 0.025(11) -0.043(10) -0.063(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 P1 O1 1.500(7) . ? P1 O3 1.520(6) . ? P1 O2 1.523(7) . ? P1 C9 1.761(11) . ? P2 O4 1.488(7) . ? P2 O6 1.493(6) . ? P2 O5 1.562(6) . ? P2 C11 1.817(9) . ? C1 C6 1.365(13) . ? C1 C2 1.476(14) . ? C1 C7 1.582(14) . ? C2 C3 1.304(13) . ? C2 H2A 0.9300 . ? C3 C4 1.473(14) . ? C3 C8 1.526(13) . ? C4 C5 1.333(12) . ? C4 C9 1.567(12) . ? C5 C6 1.408(11) . ? C5 C10 1.605(14) . ? C6 C11 1.538(13) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? O7 C13 1.430(2) . ? O7 H7 0.8200 . ? C13 C12 1.499(2) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 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 O1 P1 O3 112.0(4) . . ? O1 P1 O2 113.2(4) . . ? O3 P1 O2 109.1(4) . . ? O1 P1 C9 111.0(4) . . ? O3 P1 C9 103.5(4) . . ? O2 P1 C9 107.5(4) . . ? O4 P2 O6 116.1(4) . . ? O4 P2 O5 108.8(4) . . ? O6 P2 O5 110.2(4) . . ? O4 P2 C11 108.3(5) . . ? O6 P2 C11 109.0(4) . . ? O5 P2 C11 103.8(4) . . ? C6 C1 C2 118.6(10) . . ? C6 C1 C7 124.1(11) . . ? C2 C1 C7 117.2(10) . . ? C3 C2 C1 120.8(9) . . ? C3 C2 H2A 119.6 . . ? C1 C2 H2A 119.6 . . ? C2 C3 C4 118.9(10) . . ? C2 C3 C8 121.5(11) . . ? C4 C3 C8 119.1(11) . . ? C5 C4 C3 120.7(10) . . ? C5 C4 C9 121.3(9) . . ? C3 C4 C9 117.9(9) . . ? C4 C5 C6 120.4(9) . . ? C4 C5 C10 121.5(10) . . ? C6 C5 C10 118.1(9) . . ? C1 C6 C5 120.4(10) . . ? C1 C6 C11 119.3(10) . . ? C5 C6 C11 120.2(9) . . ? C1 C7 H7A 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C4 C9 P1 116.2(6) . . ? C4 C9 H9A 108.2 . . ? P1 C9 H9A 108.2 . . ? C4 C9 H9B 108.2 . . ? P1 C9 H9B 108.2 . . ? H9A C9 H9B 107.4 . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C6 C11 P2 114.4(6) . . ? C6 C11 H11A 108.7 . . ? P2 C11 H11A 108.7 . . ? C6 C11 H11B 108.6 . . ? P2 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C13 O7 H7 109.5 . . ? O7 C13 C12 113.8(9) . . ? O7 C13 H13A 108.8 . . ? C12 C13 H13A 108.8 . . ? O7 C13 H13B 108.8 . . ? C12 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? C13 C12 H12A 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C13 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 2.4(15) . . . . ? C7 C1 C2 C3 179.7(9) . . . . ? C1 C2 C3 C4 -4.6(14) . . . . ? C1 C2 C3 C8 -176.0(9) . . . . ? C2 C3 C4 C5 5.0(13) . . . . ? C8 C3 C4 C5 176.7(8) . . . . ? C2 C3 C4 C9 -178.0(8) . . . . ? C8 C3 C4 C9 -6.3(12) . . . . ? C3 C4 C5 C6 -2.9(12) . . . . ? C9 C4 C5 C6 -179.8(8) . . . . ? C3 C4 C5 C10 176.9(8) . . . . ? C9 C4 C5 C10 0.0(12) . . . . ? C2 C1 C6 C5 -0.2(14) . . . . ? C7 C1 C6 C5 -177.3(8) . . . . ? C2 C1 C6 C11 177.6(8) . . . . ? C7 C1 C6 C11 0.6(14) . . . . ? C4 C5 C6 C1 0.6(13) . . . . ? C10 C5 C6 C1 -179.2(9) . . . . ? C4 C5 C6 C11 -177.2(8) . . . . ? C10 C5 C6 C11 3.0(12) . . . . ? C5 C4 C9 P1 -87.4(9) . . . . ? C3 C4 C9 P1 95.5(8) . . . . ? O1 P1 C9 C4 62.4(8) . . . . ? O3 P1 C9 C4 -177.3(7) . . . . ? O2 P1 C9 C4 -61.9(8) . . . . ? C1 C6 C11 P2 -90.8(10) . . . . ? C5 C6 C11 P2 87.1(10) . . . . ? O4 P2 C11 C6 67.7(8) . . . . ? O6 P2 C11 C6 -59.4(8) . . . . ? O5 P2 C11 C6 -176.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.498 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.091 data_newrm089relab _database_code_depnum_ccdc_archive 'CCDC 755662' #TrackingRef '- murugavel_phosphonic.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H23 O10 P3' _chemical_formula_sum 'C12 H23 O10 P3' _chemical_formula_weight 420.21 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 monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.7623(7) _cell_length_b 17.876(2) _cell_length_c 10.4978(8) _cell_angle_alpha 90.00 _cell_angle_beta 107.936(9) _cell_angle_gamma 90.00 _cell_volume 1743.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2451 _cell_measurement_theta_min 3.0527 _cell_measurement_theta_max 32.252 _exptl_crystal_description block _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.601 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.392 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTIOM X CALIBUR-S' _diffrn_measurement_method 'omega(w)-q scan' _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5382 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2956 _reflns_number_gt 2365 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; ? ; _computing_cell_refinement ; ? ; _computing_data_reduction ; ? ; _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0652P)^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 2956 _refine_ls_number_parameters 261 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.1055 _refine_ls_wR_factor_gt 0.1009 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_restrained_S_all 1.136 _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 C1 C 0.8784(3) -0.11044(12) 0.6704(2) 0.0166(5) Uani 1 1 d . . . H1A H 0.7782 -0.1251 0.6618 0.020 Uiso 1 1 calc R . . H1B H 0.9433 -0.1502 0.7208 0.020 Uiso 1 1 calc R . . C2 C 0.6499(2) -0.00722(13) 0.6580(2) 0.0170(5) Uani 1 1 d . . . H2A H 0.6266 -0.0541 0.6953 0.025 Uiso 1 1 calc R . . H2B H 0.6394 -0.0142 0.5629 0.025 Uiso 1 1 calc R . . H2C H 0.5843 0.0322 0.6679 0.025 Uiso 1 1 calc R . . C3 C 0.7191(3) 0.14517(13) 0.7711(2) 0.0168(5) Uani 1 1 d . . . H3A H 0.7511 0.1810 0.8464 0.020 Uiso 1 1 calc R . . H3B H 0.6309 0.1204 0.7778 0.020 Uiso 1 1 calc R . . C4 C 1.0148(3) 0.18198(13) 0.9195(2) 0.0213(6) Uani 1 1 d . . . H4A H 0.9598 0.2190 0.8551 0.032 Uiso 1 1 calc R . . H4B H 1.1180 0.1914 0.9382 0.032 Uiso 1 1 calc R . . H4C H 0.9898 0.1858 1.0028 0.032 Uiso 1 1 calc R . . C5 C 1.2392(2) 0.06700(14) 0.9728(2) 0.0179(5) Uani 1 1 d . . . H5A H 1.2835 0.0204 1.0182 0.021 Uiso 1 1 calc R . . H5B H 1.2333 0.1028 1.0430 0.021 Uiso 1 1 calc R . . C6 C 1.1697(3) -0.08135(14) 0.8508(2) 0.0195(5) Uani 1 1 d . . . H6A H 1.1269 -0.1282 0.8084 0.029 Uiso 1 1 calc R . . H6B H 1.2119 -0.0891 0.9474 0.029 Uiso 1 1 calc R . . H6C H 1.2450 -0.0654 0.8129 0.029 Uiso 1 1 calc R . . C7 C 0.9137(2) -0.03744(12) 0.7462(2) 0.0131(5) Uani 1 1 d . . . C8 C 0.8027(2) 0.01486(12) 0.7318(2) 0.0125(5) Uani 1 1 d . . . C9 C 0.8362(3) 0.08581(13) 0.7877(2) 0.0151(5) Uani 1 1 d . . . C10 C 0.9792(3) 0.10418(12) 0.8615(2) 0.0152(5) Uani 1 1 d . . . C11 C 1.0864(2) 0.04935(13) 0.8834(2) 0.0138(5) Uani 1 1 d . . . C12 C 1.0554(2) -0.02204(13) 0.8258(2) 0.0143(5) Uani 1 1 d . . . O1 O 1.0640(2) -0.10113(11) 0.52080(18) 0.0201(4) Uani 1 1 d . . . O2 O 0.8418(2) -0.17499(9) 0.43320(16) 0.0230(4) Uani 1 1 d . . . O3 O 0.82638(18) -0.03255(9) 0.43476(14) 0.0181(4) Uani 1 1 d . . . O4 O 0.81843(19) 0.21841(10) 0.58804(17) 0.0241(4) Uani 1 1 d . . . O5 O 0.5915(2) 0.14193(10) 0.50709(17) 0.0266(5) Uani 1 1 d . . . O6 O 0.59553(18) 0.26685(9) 0.62601(16) 0.0219(4) Uani 1 1 d . . . O7 O 1.50477(18) 0.11533(11) 0.98763(17) 0.0219(4) Uani 1 1 d . . . O8 O 1.38249(18) 0.04526(10) 0.79049(17) 0.0208(4) Uani 1 1 d . . . O9 O 1.29278(17) 0.17615(9) 0.81273(15) 0.0189(4) Uani 1 1 d . . . O10 O 0.4393(2) 0.19708(10) 0.29010(17) 0.0217(4) Uani 1 1 d . . . P1 P 0.89894(7) -0.10149(3) 0.50610(6) 0.01526(18) Uani 1 1 d . . . P2 P 0.67428(7) 0.19671(4) 0.61668(6) 0.01742(19) Uani 1 1 d . . . P3 P 1.35396(7) 0.10555(3) 0.88574(6) 0.01551(19) Uani 1 1 d . . . H1 H 0.808(4) -0.167(2) 0.349(4) 0.064(11) Uiso 1 1 d . . . H2 H 1.092(5) -0.068(3) 0.526(5) 0.092(19) Uiso 1 1 d . . . H4 H 0.861(3) 0.1762(18) 0.567(3) 0.042(9) Uiso 1 1 d . . . H5 H 0.548(4) 0.163(2) 0.440(4) 0.067(13) Uiso 1 1 d . . . H7 H 1.517(3) 0.1567(19) 1.027(3) 0.041(9) Uiso 1 1 d . . . H8 H 1.315(4) 0.0380(18) 0.716(3) 0.053(10) Uiso 1 1 d . . . H10A H 0.497(5) 0.208(2) 0.234(4) 0.080(13) Uiso 1 1 d . . . H10B H 0.386(3) 0.2349(18) 0.299(3) 0.036(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0175(12) 0.0140(13) 0.0186(11) 0.0021(9) 0.0062(10) 0.0016(10) C2 0.0125(12) 0.0163(13) 0.0209(11) -0.0029(10) 0.0034(10) -0.0032(10) C3 0.0152(11) 0.0159(13) 0.0203(11) -0.0001(10) 0.0071(10) 0.0006(10) C4 0.0164(12) 0.0183(13) 0.0292(13) -0.0065(10) 0.0071(10) -0.0012(10) C5 0.0148(12) 0.0223(13) 0.0162(11) -0.0012(10) 0.0044(9) -0.0035(11) C6 0.0158(12) 0.0217(13) 0.0195(12) 0.0010(10) 0.0030(10) 0.0041(11) C7 0.0150(12) 0.0123(12) 0.0142(10) 0.0006(9) 0.0079(9) -0.0025(10) C8 0.0126(12) 0.0132(12) 0.0115(10) 0.0007(9) 0.0036(9) -0.0008(10) C9 0.0145(12) 0.0175(13) 0.0153(11) 0.0031(9) 0.0076(10) 0.0026(10) C10 0.0157(12) 0.0172(13) 0.0152(11) -0.0017(9) 0.0085(10) -0.0013(10) C11 0.0118(11) 0.0182(13) 0.0125(10) 0.0000(9) 0.0055(9) -0.0023(10) C12 0.0138(12) 0.0177(13) 0.0131(10) 0.0022(9) 0.0067(9) 0.0002(10) O1 0.0221(10) 0.0168(11) 0.0229(9) -0.0002(7) 0.0092(8) 0.0031(8) O2 0.0327(11) 0.0152(9) 0.0173(9) -0.0009(7) 0.0022(8) -0.0018(8) O3 0.0216(9) 0.0154(9) 0.0167(8) -0.0010(7) 0.0051(7) -0.0017(7) O4 0.0254(10) 0.0201(10) 0.0337(10) 0.0035(8) 0.0191(8) 0.0035(8) O5 0.0347(11) 0.0188(11) 0.0219(9) 0.0004(8) 0.0024(8) 0.0004(9) O6 0.0230(9) 0.0195(9) 0.0247(8) 0.0033(7) 0.0097(7) 0.0064(8) O7 0.0143(9) 0.0222(11) 0.0256(9) -0.0046(8) 0.0009(8) -0.0024(8) O8 0.0156(9) 0.0252(10) 0.0211(9) -0.0028(7) 0.0051(7) 0.0025(8) O9 0.0168(9) 0.0195(9) 0.0192(8) 0.0000(7) 0.0037(7) -0.0026(8) O10 0.0242(10) 0.0176(10) 0.0245(9) 0.0004(7) 0.0094(8) 0.0036(8) P1 0.0179(3) 0.0124(3) 0.0150(3) -0.0005(2) 0.0044(3) 0.0004(3) P2 0.0177(3) 0.0161(4) 0.0194(3) 0.0015(2) 0.0072(3) 0.0023(3) P3 0.0115(3) 0.0187(4) 0.0157(3) -0.0013(2) 0.0033(3) -0.0008(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 C1 C7 1.512(3) . ? C1 P1 1.803(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C8 1.507(3) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C9 1.530(3) . ? C3 P2 1.798(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C10 1.515(3) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C11 1.531(3) . ? C5 P3 1.788(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C12 1.503(3) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.403(3) . ? C7 C12 1.405(3) . ? C8 C9 1.394(3) . ? C9 C10 1.411(3) . ? C10 C11 1.400(3) . ? C11 C12 1.405(3) . ? O1 P1 1.571(2) . ? O1 H2 0.65(5) . ? O2 P1 1.5364(17) . ? O2 H1 0.86(4) . ? O3 P1 1.5015(17) . ? O4 P2 1.5753(19) . ? O4 H4 0.92(3) . ? O5 P2 1.5370(18) . ? O5 H5 0.79(4) . ? O6 P2 1.4897(17) . ? O7 P3 1.5403(17) . ? O7 H7 0.84(3) . ? O8 P3 1.5526(17) . ? O8 H8 0.87(3) . ? O9 P3 1.5016(16) . ? O10 H10A 0.95(5) . ? O10 H10B 0.88(3) . ? 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 C7 C1 P1 110.64(16) . . ? C7 C1 H1A 109.5 . . ? P1 C1 H1A 109.5 . . ? C7 C1 H1B 109.5 . . ? P1 C1 H1B 109.5 . . ? H1A C1 H1B 108.1 . . ? C8 C2 H2A 109.5 . . ? C8 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C8 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C9 C3 P2 115.10(16) . . ? C9 C3 H3A 108.5 . . ? P2 C3 H3A 108.5 . . ? C9 C3 H3B 108.5 . . ? P2 C3 H3B 108.5 . . ? H3A C3 H3B 107.5 . . ? C10 C4 H4A 109.5 . . ? C10 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C10 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C11 C5 P3 114.30(15) . . ? C11 C5 H5A 108.7 . . ? P3 C5 H5A 108.7 . . ? C11 C5 H5B 108.7 . . ? P3 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? C12 C6 H6A 109.5 . . ? C12 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C12 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C12 121.3(2) . . ? C8 C7 C1 118.4(2) . . ? C12 C7 C1 120.3(2) . . ? C9 C8 C7 119.2(2) . . ? C9 C8 C2 121.4(2) . . ? C7 C8 C2 119.4(2) . . ? C8 C9 C10 120.5(2) . . ? C8 C9 C3 120.9(2) . . ? C10 C9 C3 118.6(2) . . ? C11 C10 C9 119.4(2) . . ? C11 C10 C4 120.6(2) . . ? C9 C10 C4 120.0(2) . . ? C10 C11 C12 121.0(2) . . ? C10 C11 C5 119.6(2) . . ? C12 C11 C5 119.4(2) . . ? C11 C12 C7 118.4(2) . . ? C11 C12 C6 121.0(2) . . ? C7 C12 C6 120.5(2) . . ? P1 O1 H2 114(5) . . ? P1 O2 H1 110(2) . . ? P2 O4 H4 110(2) . . ? P2 O5 H5 113(3) . . ? P3 O7 H7 114(2) . . ? P3 O8 H8 117(2) . . ? H10A O10 H10B 113(3) . . ? O3 P1 O2 114.23(9) . . ? O3 P1 O1 110.96(10) . . ? O2 P1 O1 104.86(11) . . ? O3 P1 C1 112.06(10) . . ? O2 P1 C1 105.68(10) . . ? O1 P1 C1 108.60(11) . . ? O6 P2 O5 115.00(10) . . ? O6 P2 O4 108.34(10) . . ? O5 P2 O4 107.97(10) . . ? O6 P2 C3 111.05(10) . . ? O5 P2 C3 105.93(11) . . ? O4 P2 C3 108.34(10) . . ? O9 P3 O7 113.83(10) . . ? O9 P3 O8 112.13(9) . . ? O7 P3 O8 101.73(10) . . ? O9 P3 C5 111.82(11) . . ? O7 P3 C5 107.70(10) . . ? O8 P3 C5 109.07(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag P1 C1 C7 C8 88.6(2) . . . . ? P1 C1 C7 C12 -89.6(2) . . . . ? C12 C7 C8 C9 5.8(3) . . . . ? C1 C7 C8 C9 -172.40(19) . . . . ? C12 C7 C8 C2 -173.32(19) . . . . ? C1 C7 C8 C2 8.5(3) . . . . ? C7 C8 C9 C10 -1.9(3) . . . . ? C2 C8 C9 C10 177.2(2) . . . . ? C7 C8 C9 C3 178.32(19) . . . . ? C2 C8 C9 C3 -2.6(3) . . . . ? P2 C3 C9 C8 -83.2(2) . . . . ? P2 C3 C9 C10 97.0(2) . . . . ? C8 C9 C10 C11 -3.0(3) . . . . ? C3 C9 C10 C11 176.8(2) . . . . ? C8 C9 C10 C4 178.8(2) . . . . ? C3 C9 C10 C4 -1.5(3) . . . . ? C9 C10 C11 C12 4.2(3) . . . . ? C4 C10 C11 C12 -177.6(2) . . . . ? C9 C10 C11 C5 -175.0(2) . . . . ? C4 C10 C11 C5 3.2(3) . . . . ? P3 C5 C11 C10 -89.8(2) . . . . ? P3 C5 C11 C12 91.0(2) . . . . ? C10 C11 C12 C7 -0.5(3) . . . . ? C5 C11 C12 C7 178.76(19) . . . . ? C10 C11 C12 C6 -179.1(2) . . . . ? C5 C11 C12 C6 0.1(3) . . . . ? C8 C7 C12 C11 -4.6(3) . . . . ? C1 C7 C12 C11 173.56(19) . . . . ? C8 C7 C12 C6 174.1(2) . . . . ? C1 C7 C12 C6 -7.8(3) . . . . ? C7 C1 P1 O3 -47.83(19) . . . . ? C7 C1 P1 O2 -172.83(16) . . . . ? C7 C1 P1 O1 75.10(18) . . . . ? C9 C3 P2 O6 -162.64(16) . . . . ? C9 C3 P2 O5 71.86(19) . . . . ? C9 C3 P2 O4 -43.8(2) . . . . ? C11 C5 P3 O9 57.7(2) . . . . ? C11 C5 P3 O7 -176.51(17) . . . . ? C11 C5 P3 O8 -66.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.411 _refine_diff_density_min -0.462 _refine_diff_density_rms 0.066