# Electronic Supplementary Material (ESI) for RSC Advances # 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_COMP1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H9 O5 P' _chemical_formula_sum 'C8 H9 O5 P' _chemical_formula_weight 216.12 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 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.4760(11) _cell_length_b 5.2150(10) _cell_length_c 33.117(7) _cell_angle_alpha 90.00 _cell_angle_beta 94.12(1) _cell_angle_gamma 90.00 _cell_volume 943.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3845 _cell_measurement_theta_min 3.70 _cell_measurement_theta_max 28.91 _exptl_crystal_description paralellepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 1.52 _exptl_crystal_density_diffrn 1.522 _exptl_crystal_density_method floatation _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.284 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9261 _exptl_absorpt_correction_T_max 0.9692 _exptl_absorpt_process_details ; Oxford Diffraction Poland, CrysAlis Red, Version 171.32.6, 2008 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'KUMA KM-4 with area CCD detector' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11944 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 3.70 _diffrn_reflns_theta_max 28.91 _reflns_number_total 2479 _reflns_number_gt 1791 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; Oxford Diffraction Poland, CrysAlis CCD, Version 171.32.6, 2008 ; _computing_cell_refinement ; Oxford Diffraction Poland, CrysAlis Red, Version 171.32.6, 2008 ; _computing_data_reduction ; Oxford Diffraction Poland, CrysAlis Red, Version 171.32.6, 2008 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Brandenburg & Putz, DIAMOND Version 3.0, Crystal Impact GbR, Bonn, Germany, (2006) ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0403P)^2^+0.1514P] 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 2479 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0572 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0771 _refine_ls_wR_factor_gt 0.0696 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 0.01455(6) 0.51402(6) 0.211675(10) 0.02467(11) Uani 1 1 d . . . O1 O -0.03490(17) 0.36587(19) 0.24882(3) 0.0325(2) Uani 1 1 d . . . O2 O -0.0819(2) 0.79224(19) 0.21295(3) 0.0341(2) Uani 1 1 d . . . H2O H -0.212(3) 0.810(3) 0.2269(5) 0.051 Uiso 1 1 d . . . O3 O 0.29010(18) 0.5387(2) 0.20487(3) 0.0346(2) Uani 1 1 d . . . H3O H 0.370(3) 0.644(3) 0.2202(6) 0.052 Uiso 1 1 d . . . C1 C -0.1100(2) 0.5197(3) 0.12918(4) 0.0289(3) Uani 1 1 d . . . C2 C 0.0638(3) 0.4721(3) 0.10181(4) 0.0317(3) Uani 1 1 d . . . H2 H 0.1747 0.3386 0.1066 0.038 Uiso 1 1 calc R . . C3 C 0.0745(3) 0.6217(3) 0.06716(4) 0.0337(3) Uani 1 1 d . . . C4 C -0.2654(3) 0.8680(3) 0.08702(5) 0.0423(4) Uani 1 1 d . . . H4 H -0.3764 1.0013 0.0822 0.051 Uiso 1 1 calc R . . C5 C -0.0905(3) 0.8215(3) 0.06007(4) 0.0396(4) Uani 1 1 d . . . H5 H -0.0829 0.9237 0.0372 0.048 Uiso 1 1 calc R . . C6 C -0.2770(3) 0.7181(3) 0.12111(4) 0.0374(3) Uani 1 1 d . . . H6 H -0.3975 0.7496 0.1389 0.045 Uiso 1 1 calc R . . C7 C -0.1204(3) 0.3605(3) 0.16721(4) 0.0311(3) Uani 1 1 d . . . H7A H -0.0368 0.1992 0.1635 0.047 Uiso 1 1 calc R . . H7B H -0.2902 0.3220 0.1713 0.047 Uiso 1 1 calc R . . C8 C 0.2567(3) 0.5651(3) 0.03754(4) 0.0361(3) Uani 1 1 d . . . O4 O 0.3900(2) 0.3678(2) 0.04339(4) 0.0513(3) Uani 1 1 d . . . H4O H 0.512(4) 0.346(4) 0.0243(7) 0.077 Uiso 1 1 d . . . O5 O 0.2732(2) 0.7127(2) 0.00787(3) 0.0536(3) Uani 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 0.02500(18) 0.02571(19) 0.02408(17) 0.00069(13) 0.00711(12) -0.00055(15) O1 0.0314(5) 0.0376(6) 0.0293(5) 0.0080(4) 0.0078(4) 0.0032(4) O2 0.0404(6) 0.0277(5) 0.0361(5) 0.0012(4) 0.0147(4) 0.0024(5) O3 0.0267(5) 0.0420(6) 0.0360(5) -0.0084(5) 0.0093(4) -0.0047(4) C1 0.0333(7) 0.0269(7) 0.0260(6) -0.0016(5) -0.0017(5) -0.0035(6) C2 0.0376(8) 0.0287(7) 0.0282(7) 0.0002(6) -0.0002(6) 0.0026(6) C3 0.0420(9) 0.0327(8) 0.0261(7) -0.0009(6) 0.0009(6) 0.0017(6) C4 0.0474(10) 0.0403(9) 0.0387(8) 0.0033(7) -0.0009(7) 0.0155(7) C5 0.0496(10) 0.0380(9) 0.0310(7) 0.0070(6) 0.0009(6) 0.0075(7) C6 0.0373(9) 0.0429(9) 0.0321(7) -0.0018(6) 0.0037(6) 0.0044(7) C7 0.0357(8) 0.0283(8) 0.0295(7) -0.0002(6) 0.0033(6) -0.0061(6) C8 0.0438(9) 0.0373(8) 0.0274(7) 0.0038(6) 0.0034(6) 0.0044(7) O4 0.0634(8) 0.0497(7) 0.0430(6) 0.0123(5) 0.0199(6) 0.0220(6) O5 0.0681(8) 0.0564(8) 0.0381(6) 0.0174(5) 0.0163(5) 0.0181(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 P1 O1 1.4938(10) . ? P1 O2 1.5457(11) . ? P1 O3 1.5470(11) . ? P1 C7 1.7884(14) . ? O2 H2O 0.883(18) . ? O3 H3O 0.847(19) . ? C1 C2 1.383(2) . ? C1 C6 1.394(2) . ? C1 C7 1.5132(19) . ? C2 C3 1.3922(19) . ? C2 H2 0.9300 . ? C3 C5 1.388(2) . ? C3 C8 1.478(2) . ? C4 C5 1.377(2) . ? C4 C6 1.379(2) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 O5 1.2566(17) . ? C8 O4 1.2681(18) . ? O4 H4O 0.96(2) . ? 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 112.36(6) . . ? O1 P1 O3 113.54(6) . . ? O2 P1 O3 105.35(6) . . ? O1 P1 C7 110.97(6) . . ? O2 P1 C7 108.71(7) . . ? O3 P1 C7 105.49(7) . . ? P1 O2 H2O 113.9(12) . . ? P1 O3 H3O 115.6(12) . . ? C2 C1 C6 118.74(13) . . ? C2 C1 C7 121.06(13) . . ? C6 C1 C7 120.19(13) . . ? C1 C2 C3 120.74(13) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C5 C3 C2 119.66(14) . . ? C5 C3 C8 119.97(13) . . ? C2 C3 C8 120.36(13) . . ? C5 C4 C6 120.43(14) . . ? C5 C4 H4 119.8 . . ? C6 C4 H4 119.8 . . ? C4 C5 C3 119.79(14) . . ? C4 C5 H5 120.1 . . ? C3 C5 H5 120.1 . . ? C4 C6 C1 120.62(14) . . ? C4 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? C1 C7 P1 113.69(10) . . ? C1 C7 H7A 108.8 . . ? P1 C7 H7A 108.8 . . ? C1 C7 H7B 108.8 . . ? P1 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? O5 C8 O4 122.91(14) . . ? O5 C8 C3 119.11(13) . . ? O4 C8 C3 117.98(13) . . ? C8 O4 H4O 114.6(13) . . ? 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 O2 H2O O1 0.883(18) 1.676(19) 2.5563(15) 175.4(18) 2_455 O3 H3O O1 0.847(19) 1.754(19) 2.6008(15) 179.1(18) 2 O4 H4O O5 0.96(2) 1.67(2) 2.6288(17) 176(2) 3_665 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.91 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.261 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.046 _database_code_depnum_ccdc_archive 'CCDC 945965' ####################################################################### # # 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_COMP2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H22 Ca O13 P2' _chemical_formula_sum 'C16 H22 Ca O13 P2' _chemical_formula_weight 524.36 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' Ca Ca 0.2262 0.3064 '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 2/c' _symmetry_space_group_name_Hall '-P 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 16.6389(22) _cell_length_b 7.1141(12) _cell_length_c 9.1040(17) _cell_angle_alpha 90.00 _cell_angle_beta 95.46(1) _cell_angle_gamma 90.00 _cell_volume 1072.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2521 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 28.42 _exptl_crystal_description paralellepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 1.62 _exptl_crystal_density_diffrn 1.623 _exptl_crystal_density_method floatation _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.509 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8411 _exptl_absorpt_correction_T_max 0.9353 _exptl_absorpt_process_details ; CrysAlis Red, Ver. 171.32.6, Oxford Diffraction, 2008 ; _exptl_special_details ; ; _diffrn_ambient_temperature 295(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 'KUMA KM-4 with area CCD detector' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13864 _diffrn_reflns_av_R_equivalents 0.0772 _diffrn_reflns_av_sigmaI/netI 0.0886 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 28.42 _reflns_number_total 2682 _reflns_number_gt 1604 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlis CCD, Ver. 171.32.6, Oxford Diffraction, 2008 ; _computing_cell_refinement ; CrysAlis Red, Ver. 171.32.6, Oxford Diffraction, 2008 ; _computing_data_reduction ; CrysAlis Red, Ver. 171.32.6, Oxford Diffraction, 2008 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Diamond Version 3.0, (Brandenburg & Putz, 2006) ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^] 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 2682 _refine_ls_number_parameters 161 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0961 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.0689 _refine_ls_wR_factor_gt 0.0586 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ca Ca 0.5000 0.26281(8) 0.2500 0.01955(16) Uani 1 2 d S . . P1 P 0.37205(3) 0.09504(7) 0.51845(6) 0.01886(14) Uani 1 1 d . . . O1 O 0.35048(9) -0.0647(2) 0.40162(14) 0.0268(4) Uani 1 1 d . . . H1O1 H 0.3696(13) -0.045(3) 0.326(2) 0.040 Uiso 1 1 d . . . O2 O 0.42066(8) 0.24433(18) 0.45100(14) 0.0230(3) Uani 1 1 d . . . O3 O 0.41227(8) 0.00568(19) 0.65703(13) 0.0236(3) Uani 1 1 d . . . C1 C 0.27725(12) 0.1891(3) 0.5646(2) 0.0277(5) Uani 1 1 d . . . H1A H 0.2468 0.0876 0.6040 0.042 Uiso 1 1 calc R . . H1B H 0.2885 0.2803 0.6432 0.042 Uiso 1 1 calc R . . C2 C 0.22404(12) 0.2822(3) 0.4426(2) 0.0273(5) Uani 1 1 d . . . C3 C 0.17695(13) 0.1778(3) 0.3396(2) 0.0295(5) Uani 1 1 d . . . H3 H 0.1808 0.0474 0.3417 0.035 Uiso 1 1 calc R . . C4 C 0.12399(13) 0.2631(3) 0.2328(2) 0.0317(5) Uani 1 1 d . . . C5 C 0.11762(14) 0.4572(3) 0.2285(3) 0.0394(6) Uani 1 1 d . . . H5 H 0.0819 0.5154 0.1579 0.047 Uiso 1 1 calc R . . C6 C 0.16481(15) 0.5636(3) 0.3304(3) 0.0396(6) Uani 1 1 d . . . H6 H 0.1611 0.6940 0.3282 0.048 Uiso 1 1 calc R . . C7 C 0.21720(13) 0.4766(3) 0.4350(2) 0.0344(6) Uani 1 1 d . . . H7 H 0.2489 0.5499 0.5024 0.041 Uiso 1 1 calc R . . C8 C 0.07154(14) 0.1477(4) 0.1282(3) 0.0373(6) Uani 1 1 d . . . O4 O 0.02260(11) 0.2276(3) 0.03461(19) 0.0568(5) Uani 1 1 d . . . O5 O 0.07846(12) -0.0290(3) 0.1379(2) 0.0581(6) Uani 1 1 d . . . H1O5 H 0.0472(18) -0.084(4) 0.079(3) 0.087 Uiso 1 1 d . . . O6 O 0.40379(10) 0.3881(2) 0.06122(17) 0.0361(5) Uani 1 1 d . . . H1O6 H 0.4050(15) 0.493(4) 0.011(3) 0.054 Uiso 1 1 d . . . H2O6 H 0.3845(15) 0.315(4) 0.005(3) 0.054 Uiso 1 1 d . . . O7 O 0.5000 0.6076(3) 0.2500 0.0551(8) Uani 1 2 d S . . H1O7 H 0.512(2) 0.680(4) 0.310(3) 0.083 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 Ca 0.0224(3) 0.0202(3) 0.0162(3) 0.000 0.0027(3) 0.000 P1 0.0216(3) 0.0208(3) 0.0141(3) -0.0006(2) 0.0014(2) -0.0004(2) O1 0.0407(10) 0.0267(8) 0.0134(7) -0.0030(7) 0.0051(7) -0.0096(7) O2 0.0291(8) 0.0200(7) 0.0209(7) -0.0011(6) 0.0071(6) -0.0020(7) O3 0.0292(9) 0.0263(8) 0.0151(7) 0.0002(6) 0.0002(7) 0.0043(6) C1 0.0245(13) 0.0366(13) 0.0218(12) 0.0017(10) 0.0013(10) 0.0046(10) C2 0.0171(12) 0.0395(14) 0.0259(12) 0.0001(11) 0.0058(10) 0.0028(10) C3 0.0254(13) 0.0343(13) 0.0283(13) 0.0025(11) -0.0003(11) 0.0051(10) C4 0.0236(13) 0.0426(15) 0.0289(13) 0.0016(12) 0.0027(10) -0.0018(12) C5 0.0321(15) 0.0492(17) 0.0367(14) 0.0140(13) 0.0015(12) 0.0098(12) C6 0.0421(16) 0.0343(14) 0.0426(15) 0.0057(13) 0.0043(13) 0.0014(12) C7 0.0277(14) 0.0396(15) 0.0355(13) -0.0016(12) 0.0012(11) -0.0011(11) C8 0.0292(15) 0.0495(17) 0.0319(14) 0.0019(13) -0.0033(12) 0.0034(13) O4 0.0497(12) 0.0638(12) 0.0516(11) 0.0072(10) -0.0226(10) 0.0055(10) O5 0.0572(14) 0.0512(13) 0.0598(13) -0.0107(11) -0.0266(10) 0.0026(10) O6 0.0450(11) 0.0203(9) 0.0399(11) -0.0001(7) -0.0129(9) -0.0026(8) O7 0.080(2) 0.0238(14) 0.0544(19) 0.000 -0.0284(16) 0.000 _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 Ca O2 2.3597(14) 2_655 ? Ca O2 2.3597(14) . ? Ca O6 2.4057(17) 2_655 ? Ca O6 2.4057(17) . ? Ca O7 2.453(2) . ? Ca O3 2.5022(14) 4 ? Ca O3 2.5022(14) 3_656 ? P1 O2 1.5013(14) . ? P1 O3 1.5109(14) . ? P1 O1 1.5743(15) . ? P1 C1 1.800(2) . ? O1 H1O1 0.80(2) . ? O3 Ca 2.5022(14) 3_656 ? C1 C2 1.506(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.380(3) . ? C2 C7 1.389(3) . ? C3 C4 1.388(3) . ? C3 H3 0.9300 . ? C4 C5 1.385(3) . ? C4 C8 1.478(3) . ? C5 C6 1.382(3) . ? C5 H5 0.9300 . ? C6 C7 1.375(3) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 O4 1.257(3) . ? C8 O5 1.265(3) . ? O5 H1O5 0.81(3) . ? O6 H1O6 0.88(3) . ? O6 H2O6 0.77(2) . ? O7 H1O7 0.76(2) . ? 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 O2 Ca O2 173.61(7) 2_655 . ? O2 Ca O6 101.03(5) 2_655 2_655 ? O2 Ca O6 81.38(5) . 2_655 ? O2 Ca O6 81.38(5) 2_655 . ? O2 Ca O6 101.03(5) . . ? O6 Ca O6 136.51(8) 2_655 . ? O2 Ca O7 93.20(3) 2_655 . ? O2 Ca O7 93.20(3) . . ? O6 Ca O7 68.26(4) 2_655 . ? O6 Ca O7 68.26(4) . . ? O2 Ca O3 92.67(5) 2_655 4 ? O2 Ca O3 82.43(5) . 4 ? O6 Ca O3 148.39(5) 2_655 4 ? O6 Ca O3 73.38(5) . 4 ? O7 Ca O3 139.76(3) . 4 ? O2 Ca O3 82.43(5) 2_655 3_656 ? O2 Ca O3 92.67(5) . 3_656 ? O6 Ca O3 73.38(5) 2_655 3_656 ? O6 Ca O3 148.39(5) . 3_656 ? O7 Ca O3 139.76(3) . 3_656 ? O3 Ca O3 80.48(7) 4 3_656 ? O2 P1 O3 115.22(8) . . ? O2 P1 O1 109.34(8) . . ? O3 P1 O1 108.36(8) . . ? O2 P1 C1 110.53(9) . . ? O3 P1 C1 106.85(9) . . ? O1 P1 C1 106.12(10) . . ? P1 O1 H1O1 111.9(17) . . ? P1 O2 Ca 136.02(8) . . ? P1 O3 Ca 143.27(8) . 3_656 ? C2 C1 P1 117.24(14) . . ? C2 C1 H1A 108.0 . . ? P1 C1 H1A 108.0 . . ? C2 C1 H1B 108.0 . . ? P1 C1 H1B 108.0 . . ? H1A C1 H1B 107.2 . . ? C3 C2 C7 117.6(2) . . ? C3 C2 C1 121.4(2) . . ? C7 C2 C1 120.9(2) . . ? C2 C3 C4 121.5(2) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C5 C4 C3 119.8(2) . . ? C5 C4 C8 119.8(2) . . ? C3 C4 C8 120.3(2) . . ? C6 C5 C4 119.3(2) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C7 C6 C5 120.0(2) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C2 121.7(2) . . ? C6 C7 H7 119.1 . . ? C2 C7 H7 119.1 . . ? O4 C8 O5 123.1(2) . . ? O4 C8 C4 119.4(2) . . ? O5 C8 C4 117.6(2) . . ? C8 O5 H1O5 112(2) . . ? Ca O6 H1O6 130.0(16) . . ? Ca O6 H2O6 115.3(19) . . ? H1O6 O6 H2O6 105(2) . . ? Ca O7 H1O7 132(2) . . ? 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 _geom_hbond_publ_flag O1 H1O1 O3 0.80(2) 1.77(2) 2.574(2) 179(3) 4 y O5 H1O5 O4 0.81(3) 1.80(3) 2.606(2) 173(3) 3 y O6 H1O6 O2 0.88(3) 1.97(3) 2.824(2) 164(2) 4_565 y O6 H2O6 O1 0.77(2) 2.07(3) 2.819(2) 163(3) 4 y O7 H1O7 O2 0.76(2) 2.41(3) 3.0950(16) 150(3) 3_666 y O7 H1O7 O3 0.76(2) 2.57(3) 3.191(3) 139(3) 3_666 y _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.41 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.297 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.068 _database_code_depnum_ccdc_archive 'CCDC 945966' ####################################################################### # # 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_COMP3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H20 Ca O12 P2' _chemical_formula_sum 'C16 H20 Ca O12 P2' _chemical_formula_weight 506.34 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' Ca Ca 0.2262 0.3064 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.3149(11) _cell_length_b 5.7684(12) _cell_length_c 16.702(3) _cell_angle_alpha 92.08(1) _cell_angle_beta 90.42(1) _cell_angle_gamma 93.12(2) _cell_volume 510.95(18) _cell_formula_units_Z 1 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1520 _cell_measurement_theta_min 3.54 _cell_measurement_theta_max 28.11 _exptl_crystal_description paralellepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 1.64 _exptl_crystal_density_diffrn 1.646 _exptl_crystal_density_method floatation _exptl_crystal_F_000 262 _exptl_absorpt_coefficient_mu 0.528 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8804 _exptl_absorpt_correction_T_max 0.9312 _exptl_absorpt_process_details ; Oxford Diffraction Poland, CrysAlis Red, Version 171.32.6, 2008 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'KUMA KM-4 with area CCD detector' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6897 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0568 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 28.11 _reflns_number_total 2473 _reflns_number_gt 1749 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; Oxford Diffraction Poland, CrysAlis CCD, Version 171.32.6, 2008 ; _computing_cell_refinement ; Oxford Diffraction Poland, CrysAlis Red, Version 171.32.6, 2008 ; _computing_data_reduction ; Oxford Diffraction Poland, CrysAlis Red, Version 171.32.6, 2008 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Brandenburg & Putz, DIAMOND Version 3.0, Crystal Impact GbR, Bonn, Germany, (2006) ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0290P)^2^] 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 2473 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0622 _refine_ls_wR_factor_gt 0.0583 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ca Ca 0.5000 0.5000 0.5000 0.01700(12) Uani 1 2 d S . . P1 P 0.80024(7) 0.01632(7) 0.40244(2) 0.01662(11) Uani 1 1 d . . . O1 O 0.7473(2) 0.26554(17) 0.42070(6) 0.0218(3) Uani 1 1 d . . . O2 O 0.70896(19) -0.15458(17) 0.46367(6) 0.0214(3) Uani 1 1 d . . . O3 O 1.0972(2) -0.00127(18) 0.39288(6) 0.0217(3) Uani 1 1 d . . . H13 H 1.170(3) 0.038(3) 0.4347(6) 0.033 Uiso 1 1 d . . . C1 C 0.7657(3) 0.0740(3) 0.23836(9) 0.0230(4) Uani 1 1 d . . . C2 C 0.9608(3) 0.0166(3) 0.18853(9) 0.0258(4) Uani 1 1 d . . . H2 H 1.0458 -0.1170 0.1974 0.031 Uiso 1 1 calc R . . C3 C 1.0320(3) 0.1555(3) 0.12535(9) 0.0275(4) Uani 1 1 d . . . C4 C 0.9072(4) 0.3572(3) 0.11295(10) 0.0343(4) Uani 1 1 d . . . H4 H 0.9550 0.4524 0.0713 0.041 Uiso 1 1 calc R . . C5 C 0.7124(4) 0.4155(3) 0.16268(10) 0.0355(5) Uani 1 1 d . . . H5 H 0.6284 0.5500 0.1544 0.043 Uiso 1 1 calc R . . C6 C 0.6422(3) 0.2750(3) 0.22459(10) 0.0298(4) Uani 1 1 d . . . H6 H 0.5101 0.3153 0.2576 0.036 Uiso 1 1 calc R . . C7 C 0.6838(3) -0.0808(3) 0.30570(9) 0.0243(4) Uani 1 1 d . . . H7A H 0.7400 -0.2355 0.2941 0.036 Uiso 1 1 calc R . . H7B H 0.5011 -0.0920 0.3071 0.036 Uiso 1 1 calc R . . C8 C 1.2352(3) 0.0857(3) 0.07060(10) 0.0301(4) Uani 1 1 d . . . O4 O 1.2872(3) 0.2162(3) 0.01299(8) 0.0466(4) Uani 1 1 d . . . H14 H 1.410(3) 0.180(4) -0.0131(12) 0.070 Uiso 1 1 d . . . O5 O 1.3429(2) -0.0992(2) 0.08265(7) 0.0428(3) Uani 1 1 d . . . O6 O 0.2100(2) 0.5249(2) 0.39226(8) 0.0309(3) Uani 1 1 d . . . H16 H 0.179(4) 0.6602(14) 0.3842(12) 0.046 Uiso 1 1 d . . . H26 H 0.081(2) 0.441(3) 0.3951(12) 0.046 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 Ca 0.0175(3) 0.0126(2) 0.0210(2) 0.00073(18) 0.00624(19) 0.00081(18) P1 0.0177(2) 0.0138(2) 0.0183(2) -0.00054(16) 0.00608(17) 0.00064(16) O1 0.0245(6) 0.0163(6) 0.0250(6) -0.0002(4) 0.0089(5) 0.0030(5) O2 0.0232(6) 0.0179(6) 0.0230(6) 0.0021(4) 0.0075(5) -0.0015(5) O3 0.0176(6) 0.0212(6) 0.0264(6) -0.0006(5) 0.0046(5) 0.0007(5) C1 0.0242(9) 0.0277(9) 0.0165(8) -0.0027(7) 0.0006(7) -0.0030(7) C2 0.0275(10) 0.0269(9) 0.0230(8) 0.0001(7) 0.0010(7) 0.0019(7) C3 0.0292(10) 0.0331(10) 0.0199(8) -0.0001(7) 0.0033(7) -0.0013(8) C4 0.0448(12) 0.0353(10) 0.0232(9) 0.0065(8) 0.0042(8) 0.0019(9) C5 0.0454(13) 0.0327(11) 0.0295(10) 0.0026(8) 0.0023(9) 0.0102(9) C6 0.0294(10) 0.0350(10) 0.0249(9) -0.0024(8) 0.0031(8) 0.0044(8) C7 0.0254(10) 0.0240(9) 0.0227(8) -0.0025(7) 0.0041(7) -0.0036(7) C8 0.0303(11) 0.0369(11) 0.0225(9) 0.0020(8) 0.0043(8) -0.0034(9) O4 0.0489(10) 0.0611(10) 0.0321(7) 0.0156(7) 0.0215(6) 0.0123(8) O5 0.0450(9) 0.0479(9) 0.0377(7) 0.0095(6) 0.0161(6) 0.0142(7) O6 0.0286(7) 0.0183(6) 0.0456(7) 0.0028(6) -0.0044(6) 0.0005(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ca O1 2.3236(12) . ? Ca O1 2.3236(12) 2_666 ? Ca O2 2.3300(12) 1_565 ? Ca O2 2.3300(12) 2_656 ? Ca O6 2.3741(14) 2_666 ? Ca O6 2.3741(14) . ? Ca H16 2.783(16) . ? P1 O1 1.5008(11) . ? P1 O2 1.5104(11) . ? P1 O3 1.5958(12) . ? P1 C7 1.7859(17) . ? O2 Ca 2.3300(12) 1_545 ? O3 H13 0.815(12) . ? C1 C2 1.381(2) . ? C1 C6 1.389(2) . ? C1 C7 1.513(2) . ? C2 C3 1.391(2) . ? C2 H2 0.9300 . ? C3 C4 1.391(2) . ? C3 C8 1.483(2) . ? C4 C5 1.380(2) . ? C4 H4 0.9300 . ? C5 C6 1.378(2) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 O5 1.260(2) . ? C8 O4 1.266(2) . ? O4 H14 0.820(18) . ? O6 H16 0.821(11) . ? O6 H26 0.820(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 Ca O1 180.00(4) . 2_666 ? O1 Ca O2 94.34(4) . 1_565 ? O1 Ca O2 85.66(4) 2_666 1_565 ? O1 Ca O2 85.66(4) . 2_656 ? O1 Ca O2 94.34(4) 2_666 2_656 ? O2 Ca O2 180.0 1_565 2_656 ? O1 Ca O6 89.59(5) . 2_666 ? O1 Ca O6 90.41(5) 2_666 2_666 ? O2 Ca O6 89.65(5) 1_565 2_666 ? O2 Ca O6 90.35(5) 2_656 2_666 ? O1 Ca O6 90.41(5) . . ? O1 Ca O6 89.59(5) 2_666 . ? O2 Ca O6 90.35(5) 1_565 . ? O2 Ca O6 89.65(5) 2_656 . ? O6 Ca O6 180.0 2_666 . ? O1 Ca H16 100.4(4) . . ? O1 Ca H16 79.6(4) 2_666 . ? O2 Ca H16 77.4(3) 1_565 . ? O2 Ca H16 102.6(3) 2_656 . ? O6 Ca H16 164.1(3) 2_666 . ? O6 Ca H16 15.9(3) . . ? O1 P1 O2 115.75(6) . . ? O1 P1 O3 108.46(7) . . ? O2 P1 O3 108.41(6) . . ? O1 P1 C7 111.80(7) . . ? O2 P1 C7 109.18(7) . . ? O3 P1 C7 102.33(7) . . ? P1 O1 Ca 142.41(6) . . ? P1 O2 Ca 152.36(7) . 1_545 ? P1 O3 H13 110.4(12) . . ? C2 C1 C6 118.69(15) . . ? C2 C1 C7 120.94(15) . . ? C6 C1 C7 120.36(15) . . ? C1 C2 C3 120.99(15) . . ? C1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? C2 C3 C4 119.45(16) . . ? C2 C3 C8 120.11(15) . . ? C4 C3 C8 120.43(15) . . ? C5 C4 C3 119.76(16) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C6 C5 C4 120.17(16) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C1 120.93(16) . . ? C5 C6 H6 119.5 . . ? C1 C6 H6 119.5 . . ? C1 C7 P1 114.51(11) . . ? C1 C7 H7A 108.6 . . ? P1 C7 H7A 108.6 . . ? C1 C7 H7B 108.6 . . ? P1 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? O5 C8 O4 123.71(16) . . ? O5 C8 C3 119.10(15) . . ? O4 C8 C3 117.18(16) . . ? C8 O4 H14 114.5(16) . . ? Ca O6 H16 111.6(14) . . ? Ca O6 H26 115.2(14) . . ? H16 O6 H26 112(2) . . ? 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 _geom_hbond_publ_flag O3 H13 O2 0.815(13) 1.898(11) 2.7050(17) 170.7(17) 2_756 y O4 H14 O5 0.820(18) 1.828(18) 2.6430(19) 173(2) 2_855 y O6 H16 O3 0.821(11) 2.025(11) 2.8294(17) 167(2) 1_465 y O6 H26 O1 0.820(13) 2.049(13) 2.8605(18) 170(2) 1_455 y _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.11 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.318 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 945967' ####################################################################### # # 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_COMP4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H24 Ca O14 P2, C10 H8 N2' _chemical_formula_sum 'C26 H32 Ca N2 O14 P2' _chemical_formula_weight 698.56 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' Ca Ca 0.2262 0.3064 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.9848(10) _cell_length_b 6.5942(13) _cell_length_c 22.857(5) _cell_angle_alpha 85.39(1) _cell_angle_beta 84.54(1) _cell_angle_gamma 85.06(2) _cell_volume 743.2(3) _cell_formula_units_Z 1 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 525 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 28.22 _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 1.56 _exptl_crystal_density_diffrn 1.561 _exptl_crystal_density_method floatation _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.393 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9061 _exptl_absorpt_correction_T_max 0.9422 _exptl_absorpt_process_details ; Oxford Diffraction Poland, CrysAlis Red, Version 171.32.6, 2008 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'KUMA KM-4 with area CCD detector' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9903 _diffrn_reflns_av_R_equivalents 0.0519 _diffrn_reflns_av_sigmaI/netI 0.1854 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 28.22 _reflns_number_total 3646 _reflns_number_gt 1929 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; Oxford Diffraction Poland, CrysAlis CCD, Version 171.32.6, 2008 ; _computing_cell_refinement ; Oxford Diffraction Poland, CrysAlis Red, Version 171.32.6, 2008 ; _computing_data_reduction ; Oxford Diffraction Poland, CrysAlis Red, Version 171.32.6, 2008 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Brandenburg & Putz, DIAMOND Version 3.0, Crystal Impact GbR, Bonn, Germany, (2006) ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0800P)^2^] 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 0.062(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3646 _refine_ls_number_parameters 224 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1539 _refine_ls_R_factor_gt 0.0795 _refine_ls_wR_factor_ref 0.1689 _refine_ls_wR_factor_gt 0.1531 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ca Ca 0.0000 0.0000 0.0000 0.0240(3) Uani 1 2 d S . . O1W O 0.2687(6) -0.1503(4) 0.07413(13) 0.0414(7) Uani 1 1 d D . . H1W1 H 0.411(5) -0.089(7) 0.071(2) 0.062 Uiso 1 1 d D . . H2W1 H 0.320(10) -0.2753(19) 0.075(2) 0.062 Uiso 1 1 d D . . O2W O -0.2028(6) -0.3059(4) 0.00856(12) 0.0385(7) Uani 1 1 d D . . H1W2 H -0.168(9) -0.352(7) 0.0426(9) 0.058 Uiso 1 1 d D . . H2W2 H -0.185(10) -0.361(7) -0.0237(11) 0.058 Uiso 1 1 d D . . P1 P -0.41107(18) 0.27961(15) 0.11450(4) 0.0231(3) Uani 1 1 d . . . O1 O -0.3071(5) 0.1114(4) 0.07651(10) 0.0307(6) Uani 1 1 d . . . O2 O -0.6536(5) 0.4089(4) 0.09444(11) 0.0290(6) Uani 1 1 d . . . O3 O -0.1905(5) 0.4354(4) 0.11842(11) 0.0277(6) Uani 1 1 d D . . H3 H -0.039(4) 0.385(6) 0.1050(16) 0.042 Uiso 1 1 d D . . C7 C -0.5082(8) 0.1788(6) 0.18827(15) 0.0335(9) Uani 1 1 d . . . H7A H -0.5670 0.2921 0.2122 0.050 Uiso 1 1 calc R . . H7B H -0.6619 0.0989 0.1872 0.050 Uiso 1 1 calc R . . C1 C -0.2918(7) 0.0483(6) 0.21771(15) 0.0244(8) Uani 1 1 d . . . C2 C -0.1548(7) 0.1143(5) 0.26046(17) 0.0307(9) Uani 1 1 d . . . H2 H -0.1865 0.2501 0.2692 0.037 Uiso 1 1 calc R . . C3 C 0.0281(7) -0.0092(6) 0.29143(15) 0.0314(9) Uani 1 1 d . . . C4 C 0.0879(8) -0.2109(6) 0.27842(18) 0.0366(10) Uani 1 1 d . . . H4 H 0.2111 -0.2972 0.2986 0.044 Uiso 1 1 calc R . . C5 C -0.0439(10) -0.2765(8) 0.23426(19) 0.0535(13) Uani 1 1 d . . . H5 H -0.0014 -0.4101 0.2242 0.064 Uiso 1 1 calc R . . C6 C -0.2347(9) -0.1594(7) 0.20369(18) 0.0465(12) Uani 1 1 d . . . H6 H -0.3228 -0.2133 0.1751 0.056 Uiso 1 1 calc R . . C8 C 0.1816(8) 0.0721(7) 0.33726(18) 0.0406(11) Uani 1 1 d . . . O4 O 0.2102(5) 0.2682(4) 0.32938(12) 0.0333(7) Uani 1 1 d D . . H4O H 0.341(6) 0.296(7) 0.3471(17) 0.050 Uiso 1 1 d D . . O5 O 0.2793(7) -0.0401(5) 0.37650(13) 0.0557(9) Uani 1 1 d . . . C11 C 0.9056(7) 0.4734(6) 0.47933(16) 0.0307(9) Uani 1 1 d . . . C12 C 0.8471(9) 0.6016(7) 0.43081(18) 0.0454(11) Uani 1 1 d . . . H12 H 0.9252 0.7252 0.4230 0.055 Uiso 1 1 calc R . . C13 C 0.6673(10) 0.5405(8) 0.3938(2) 0.0541(13) Uani 1 1 d . . . H13 H 0.6254 0.6295 0.3617 0.065 Uiso 1 1 calc R . . N14 N 0.5527(7) 0.3682(6) 0.40056(14) 0.0417(9) Uani 1 1 d . . . C15 C 0.6216(9) 0.2463(7) 0.44546(18) 0.0488(12) Uani 1 1 d . . . H15 H 0.5473 0.1208 0.4510 0.059 Uiso 1 1 calc R . . C16 C 0.7906(9) 0.2878(7) 0.48413(18) 0.0457(12) Uani 1 1 d . . . H16 H 0.8315 0.1913 0.5146 0.055 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 Ca 0.0278(6) 0.0183(6) 0.0253(5) -0.0028(4) 0.0032(4) -0.0024(5) O1W 0.0459(18) 0.0311(17) 0.0505(17) 0.0044(15) -0.0164(14) -0.0155(15) O2W 0.0518(17) 0.0280(16) 0.0377(16) -0.0036(13) -0.0015(14) -0.0164(14) P1 0.0246(5) 0.0211(5) 0.0236(5) -0.0015(4) -0.0034(3) -0.0006(4) O1 0.0399(15) 0.0265(14) 0.0248(12) -0.0083(11) 0.0058(11) -0.0007(12) O2 0.0246(14) 0.0199(14) 0.0403(14) 0.0024(12) 0.0001(11) 0.0028(11) O3 0.0207(13) 0.0215(14) 0.0407(15) -0.0113(12) 0.0015(10) 0.0037(11) C7 0.035(2) 0.041(2) 0.0220(17) 0.0017(17) 0.0015(15) 0.0028(19) C1 0.0207(19) 0.023(2) 0.0302(18) -0.0019(16) -0.0063(14) -0.0041(16) C2 0.035(2) 0.0131(19) 0.045(2) -0.0030(17) -0.0080(17) -0.0014(17) C3 0.033(2) 0.033(2) 0.0278(18) 0.0144(17) -0.0107(15) -0.0086(19) C4 0.038(2) 0.020(2) 0.052(2) 0.0039(19) -0.0160(19) 0.0077(18) C5 0.072(3) 0.050(3) 0.038(2) -0.007(2) -0.018(2) 0.013(3) C6 0.041(3) 0.048(3) 0.058(2) -0.016(2) -0.013(2) -0.008(2) C8 0.038(2) 0.044(3) 0.042(2) -0.008(2) -0.0070(17) -0.006(2) O4 0.0322(16) 0.0271(16) 0.0433(16) -0.0038(12) -0.0109(12) -0.0075(13) O5 0.073(2) 0.056(2) 0.0443(17) 0.0163(16) -0.0360(16) -0.0248(19) C11 0.0208(19) 0.036(2) 0.036(2) -0.0008(18) -0.0020(15) -0.0086(18) C12 0.050(3) 0.050(3) 0.041(2) 0.003(2) -0.019(2) -0.019(2) C13 0.057(3) 0.051(3) 0.054(3) 0.020(2) -0.023(2) -0.008(3) N14 0.044(2) 0.046(2) 0.040(2) 0.0067(17) -0.0199(16) -0.0285(19) C15 0.065(3) 0.047(3) 0.038(2) 0.011(2) -0.015(2) -0.029(3) C16 0.056(3) 0.044(3) 0.039(2) 0.016(2) -0.017(2) -0.021(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 Ca O2W 2.319(3) . ? Ca O2W 2.319(3) 2 ? Ca O1 2.333(2) . ? Ca O1 2.333(2) 2 ? Ca O1W 2.362(3) . ? Ca O1W 2.362(3) 2 ? Ca H1W2 2.62(4) . ? Ca H2W2 2.74(4) . ? O1W H1W1 0.840(2) . ? O1W H2W1 0.840(2) . ? O2W H1W2 0.840(2) . ? O2W H2W2 0.840(2) . ? P1 O1 1.491(3) . ? P1 O2 1.505(2) . ? P1 O3 1.581(3) . ? P1 C7 1.800(4) . ? O3 H3 0.840(2) . ? C7 C1 1.498(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C1 C2 1.363(5) . ? C1 C6 1.430(6) . ? C2 C3 1.378(5) . ? C2 H2 0.9300 . ? C3 C4 1.387(5) . ? C3 C8 1.511(5) . ? C4 C5 1.372(5) . ? C4 H4 0.9300 . ? C5 C6 1.379(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C8 O5 1.226(5) . ? C8 O4 1.309(5) . ? O4 H4O 0.840(2) . ? C11 C12 1.378(6) . ? C11 C16 1.388(6) . ? C11 C11 1.477(7) 2_766 ? C12 C13 1.394(6) . ? C12 H12 0.9300 . ? C13 N14 1.306(6) . ? C13 H13 0.9300 . ? N14 C15 1.305(5) . ? C15 C16 1.337(6) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? 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 O2W Ca O2W 180.00(6) . 2 ? O2W Ca O1 88.50(10) . . ? O2W Ca O1 91.50(10) 2 . ? O2W Ca O1 91.50(10) . 2 ? O2W Ca O1 88.50(10) 2 2 ? O1 Ca O1 180.00(13) . 2 ? O2W Ca O1W 85.79(10) . . ? O2W Ca O1W 94.21(10) 2 . ? O1 Ca O1W 86.50(10) . . ? O1 Ca O1W 93.50(10) 2 . ? O2W Ca O1W 94.21(10) . 2 ? O2W Ca O1W 85.79(10) 2 2 ? O1 Ca O1W 93.50(10) . 2 ? O1 Ca O1W 86.50(10) 2 2 ? O1W Ca O1W 180.00(17) . 2 ? O2W Ca H1W2 18.3(5) . . ? O2W Ca H1W2 161.7(5) 2 . ? O1 Ca H1W2 80.8(10) . . ? O1 Ca H1W2 99.2(10) 2 . ? O1W Ca H1W2 68.9(6) . . ? O1W Ca H1W2 111.1(6) 2 . ? O2W Ca H2W2 16.7(6) . . ? O2W Ca H2W2 163.3(6) 2 . ? O1 Ca H2W2 103.3(7) . . ? O1 Ca H2W2 76.7(7) 2 . ? O1W Ca H2W2 94.3(9) . . ? O1W Ca H2W2 85.7(9) 2 . ? H1W2 Ca H2W2 33.1(9) . . ? Ca O1W H1W1 107(3) . . ? Ca O1W H2W1 120(3) . . ? H1W1 O1W H2W1 106(5) . . ? Ca O2W H1W2 102(3) . . ? Ca O2W H2W2 111(3) . . ? H1W2 O2W H2W2 131(5) . . ? O1 P1 O2 115.39(14) . . ? O1 P1 O3 111.73(14) . . ? O2 P1 O3 104.87(14) . . ? O1 P1 C7 110.55(17) . . ? O2 P1 C7 106.16(16) . . ? O3 P1 C7 107.66(16) . . ? P1 O1 Ca 147.75(16) . . ? P1 O3 H3 110(3) . . ? C1 C7 P1 115.2(3) . . ? C1 C7 H7A 108.5 . . ? P1 C7 H7A 108.5 . . ? C1 C7 H7B 108.5 . . ? P1 C7 H7B 108.5 . . ? H7A C7 H7B 107.5 . . ? C2 C1 C6 117.4(3) . . ? C2 C1 C7 122.9(3) . . ? C6 C1 C7 119.5(3) . . ? C1 C2 C3 123.5(3) . . ? C1 C2 H2 118.2 . . ? C3 C2 H2 118.2 . . ? C2 C3 C4 120.1(3) . . ? C2 C3 C8 121.7(4) . . ? C4 C3 C8 118.1(3) . . ? C5 C4 C3 116.6(4) . . ? C5 C4 H4 121.7 . . ? C3 C4 H4 121.7 . . ? C4 C5 C6 125.0(4) . . ? C4 C5 H5 117.5 . . ? C6 C5 H5 117.5 . . ? C5 C6 C1 117.3(3) . . ? C5 C6 H6 121.3 . . ? C1 C6 H6 121.3 . . ? O5 C8 O4 123.9(4) . . ? O5 C8 C3 121.9(4) . . ? O4 C8 C3 114.1(4) . . ? C8 O4 H4O 109(3) . . ? C12 C11 C16 115.6(3) . . ? C12 C11 C11 121.3(5) . 2_766 ? C16 C11 C11 122.9(4) . 2_766 ? C11 C12 C13 117.9(4) . . ? C11 C12 H12 121.0 . . ? C13 C12 H12 121.0 . . ? N14 C13 C12 125.3(4) . . ? N14 C13 H13 117.4 . . ? C12 C13 H13 117.4 . . ? C13 N14 C15 115.2(3) . . ? N14 C15 C16 125.1(4) . . ? N14 C15 H15 117.5 . . ? C16 C15 H15 117.5 . . ? C15 C16 C11 120.7(4) . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? 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 O1W H1W1 O1 0.840(2) 2.029(13) 2.849(4) 165(5) 1_655 O1W H1W1 O2W 0.840(2) 2.67(5) 3.044(4) 108(4) 1_655 O1W H2W1 O2 0.840(2) 2.091(16) 2.905(4) 163(5) 1_645 O2W H1W2 O3 0.840(2) 2.14(2) 2.922(4) 155(4) 1_545 O2W H2W2 O2 0.840(2) 1.93(3) 2.679(4) 147(5) 2_455 O3 H3 O2 0.840(2) 1.93(2) 2.674(3) 147(4) 1_655 O4 H4O N14 0.840(2) 1.806(12) 2.625(4) 165(4) . _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.22 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.698 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.096 _database_code_depnum_ccdc_archive 'CCDC 945968' ####################################################################### # # 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_COMP5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H8 O5 P, 0.5(C10 H10 N2)' _chemical_formula_sum 'C13 H13 N O5 P' _chemical_formula_weight 294.21 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' 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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 17.908(4) _cell_length_b 4.7119(9) _cell_length_c 17.201(3) _cell_angle_alpha 90.00 _cell_angle_beta 115.94(1) _cell_angle_gamma 90.00 _cell_volume 1305.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1220 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 28.55 _exptl_crystal_description parellelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 1.49 _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method floatation _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 0.230 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8952 _exptl_absorpt_correction_T_max 0.9333 _exptl_absorpt_process_details ; Oxford Diffraction Poland, CrysAlis Red, Version 171.32.6, 2008 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'KUMA KM-4 with area CCD detector' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16768 _diffrn_reflns_av_R_equivalents 0.0857 _diffrn_reflns_av_sigmaI/netI 0.1876 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 28.55 _reflns_number_total 3293 _reflns_number_gt 1926 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; Oxford Diffraction Poland, CrysAlis CCD, Version 171.32.6, 2008 ; _computing_cell_refinement ; Oxford Diffraction Poland, CrysAlis Red, Version 171.32.6, 2008 ; _computing_data_reduction ; Oxford Diffraction Poland, CrysAlis Red, Version 171.32.6, 2008 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Brandenburg & Putz, DIAMOND Version 3.0, Crystal Impact GbR, Bonn, Germany, (2006) ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0120P)^2^] 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 3293 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1461 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.0589 _refine_ls_wR_factor_gt 0.0533 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.002 _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 0.19985(4) 0.52494(14) 0.35740(4) 0.03667(18) Uani 1 1 d . . . O1 O 0.21123(9) 0.7864(3) 0.41170(9) 0.0400(4) Uani 1 1 d . . . O2 O 0.14465(8) 0.5749(3) 0.26247(8) 0.0453(5) Uani 1 1 d . . . O3 O 0.15991(11) 0.2887(3) 0.39088(11) 0.0505(5) Uani 1 1 d . . . H3O H 0.1789(15) 0.121(5) 0.3956(15) 0.076 Uiso 1 1 d . . . C1 C 0.29811(12) 0.3853(5) 0.37236(13) 0.0394(6) Uani 1 1 d . . . H1A H 0.3317 0.3498 0.4335 0.059 Uiso 1 1 calc R . . H1B H 0.2892 0.2049 0.3424 0.059 Uiso 1 1 calc R . . C2 C 0.34517(15) 0.5791(5) 0.34000(15) 0.0366(6) Uani 1 1 d . . . C3 C 0.32217(13) 0.6078(5) 0.25285(15) 0.0393(7) Uani 1 1 d . . . H3 H 0.2766 0.5066 0.2138 0.047 Uiso 1 1 calc R . . C4 C 0.36531(15) 0.7847(5) 0.22151(16) 0.0390(6) Uani 1 1 d . . . C5 C 0.43310(15) 0.9315(5) 0.28039(17) 0.0505(7) Uani 1 1 d . . . H5 H 0.4629 1.0503 0.2610 0.061 Uiso 1 1 calc R . . C6 C 0.45684(15) 0.9031(6) 0.36764(18) 0.0615(9) Uani 1 1 d . . . H6 H 0.5026 1.0033 0.4068 0.074 Uiso 1 1 calc R . . C7 C 0.41361(15) 0.7279(5) 0.39746(15) 0.0487(7) Uani 1 1 d . . . H7 H 0.4305 0.7095 0.4566 0.058 Uiso 1 1 calc R . . C8 C 0.34184(18) 0.8129(6) 0.12760(18) 0.0530(8) Uani 1 1 d . . . O4 O 0.38215(12) 0.9299(5) 0.09785(11) 0.0929(8) Uani 1 1 d . . . O5 O 0.26951(12) 0.6941(4) 0.07931(10) 0.0655(6) Uani 1 1 d . . . H5O H 0.2582(16) 0.690(6) 0.0259(17) 0.098 Uiso 1 1 d . . . N1 N 0.09114(13) -0.0056(4) 0.16223(11) 0.0396(5) Uani 1 1 d . . . H1N H 0.1137(12) -0.150(3) 0.1989(10) 0.047 Uiso 1 1 d . . . C9 C 0.01775(15) 0.1012(5) 0.14687(15) 0.0512(8) Uani 1 1 d . . . H9 H -0.0090 0.0407 0.1797 0.061 Uiso 1 1 calc R . . C10 C -0.01959(14) 0.2998(5) 0.08333(14) 0.0453(7) Uani 1 1 d . . . H10 H -0.0717 0.3701 0.0727 0.054 Uiso 1 1 calc R . . C11 C 0.01981(14) 0.3958(4) 0.03506(12) 0.0312(6) Uani 1 1 d . . . C12 C 0.09648(14) 0.2825(5) 0.05375(14) 0.0435(7) Uani 1 1 d . . . H12 H 0.1254 0.3415 0.0230 0.052 Uiso 1 1 calc R . . C13 C 0.13033(15) 0.0841(5) 0.11724(15) 0.0500(8) Uani 1 1 d . . . H13 H 0.1824 0.0099 0.1292 0.060 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 0.0452(4) 0.0316(4) 0.0378(3) 0.0060(4) 0.0224(3) 0.0059(4) O1 0.0516(11) 0.0317(10) 0.0418(9) 0.0005(8) 0.0265(9) 0.0072(9) O2 0.0486(10) 0.0424(12) 0.0360(9) 0.0061(8) 0.0097(8) 0.0021(9) O3 0.0646(12) 0.0472(11) 0.0734(12) 0.0202(11) 0.0543(11) 0.0093(10) C1 0.0482(16) 0.0338(15) 0.0431(14) 0.0068(12) 0.0264(13) 0.0087(13) C2 0.0365(15) 0.0392(18) 0.0372(14) 0.0027(14) 0.0189(13) 0.0066(14) C3 0.0361(15) 0.0387(17) 0.0474(16) 0.0011(14) 0.0222(14) 0.0010(14) C4 0.0381(15) 0.0432(18) 0.0422(15) 0.0006(14) 0.0236(14) 0.0015(15) C5 0.0459(17) 0.053(2) 0.0653(18) -0.0017(17) 0.0362(16) -0.0070(16) C6 0.0488(18) 0.068(2) 0.064(2) -0.0220(18) 0.0219(17) -0.0161(17) C7 0.0490(17) 0.058(2) 0.0400(15) -0.0037(16) 0.0198(15) 0.0060(17) C8 0.052(2) 0.059(2) 0.0562(19) 0.0003(17) 0.0310(18) 0.0011(17) O4 0.0849(15) 0.144(2) 0.0618(12) 0.0083(13) 0.0432(11) -0.0461(15) O5 0.0658(13) 0.0959(16) 0.0387(12) 0.0017(12) 0.0265(13) -0.0219(12) N1 0.0497(15) 0.0291(14) 0.0326(11) 0.0045(11) 0.0113(12) 0.0030(14) C9 0.0454(17) 0.056(2) 0.0576(17) 0.0110(16) 0.0274(16) 0.0030(16) C10 0.0368(15) 0.0491(19) 0.0508(17) 0.0138(15) 0.0198(15) 0.0121(15) C11 0.0339(15) 0.0255(17) 0.0331(14) -0.0055(11) 0.0136(13) -0.0014(13) C12 0.0493(17) 0.0460(18) 0.0470(15) 0.0143(14) 0.0321(14) 0.0118(15) C13 0.0457(17) 0.055(2) 0.0566(18) -0.0001(16) 0.0288(15) 0.0103(15) _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 1.5051(14) . ? P1 O2 1.5122(14) . ? P1 O3 1.5629(16) . ? P1 C1 1.789(2) . ? O3 H3O 0.85(2) . ? C1 C2 1.505(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.377(3) . ? C2 C7 1.382(3) . ? C3 C4 1.395(3) . ? C3 H3 0.9300 . ? C4 C5 1.379(3) . ? C4 C8 1.486(3) . ? C5 C6 1.376(3) . ? C5 H5 0.9300 . ? C6 C7 1.375(3) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 O4 1.188(3) . ? C8 O5 1.319(3) . ? O5 H5O 0.85(3) . ? N1 C13 1.321(3) . ? N1 C9 1.322(3) . ? N1 H1N 0.89(2) . ? C9 C10 1.370(3) . ? C9 H9 0.9300 . ? C10 C11 1.380(3) . ? C10 H10 0.9300 . ? C11 C12 1.374(3) . ? C11 C11 1.474(4) 3_565 ? C12 C13 1.362(3) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? 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 112.94(9) . . ? O1 P1 O3 108.30(9) . . ? O2 P1 O3 108.69(10) . . ? O1 P1 C1 110.74(10) . . ? O2 P1 C1 110.48(10) . . ? O3 P1 C1 105.36(10) . . ? P1 O3 H3O 117.9(17) . . ? C2 C1 P1 113.47(15) . . ? C2 C1 H1A 108.9 . . ? P1 C1 H1A 108.9 . . ? C2 C1 H1B 108.9 . . ? P1 C1 H1B 108.9 . . ? H1A C1 H1B 107.7 . . ? C3 C2 C7 118.6(2) . . ? C3 C2 C1 120.9(2) . . ? C7 C2 C1 120.6(2) . . ? C2 C3 C4 121.8(2) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C5 C4 C3 118.3(2) . . ? C5 C4 C8 119.5(2) . . ? C3 C4 C8 122.2(2) . . ? C6 C5 C4 120.3(2) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C7 C6 C5 120.6(2) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C2 120.4(2) . . ? C6 C7 H7 119.8 . . ? C2 C7 H7 119.8 . . ? O4 C8 O5 122.7(3) . . ? O4 C8 C4 125.0(3) . . ? O5 C8 C4 112.3(2) . . ? C8 O5 H5O 113.2(19) . . ? C13 N1 C9 119.8(2) . . ? C13 N1 H1N 117.7(14) . . ? C9 N1 H1N 122.2(14) . . ? N1 C9 C10 121.0(2) . . ? N1 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C9 C10 C11 120.3(2) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C12 C11 C10 117.0(2) . . ? C12 C11 C11 121.6(3) . 3_565 ? C10 C11 C11 121.4(3) . 3_565 ? C13 C12 C11 120.2(2) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? N1 C13 C12 121.7(2) . . ? N1 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? 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 O3 H3O O1 0.85(2) 1.66(2) 2.507(2) 174(2) 1_545 N1 H1N O2 0.89(2) 1.63(2) 2.520(2) 174(2) 1_545 O5 H5O O1 0.85(3) 1.77(3) 2.603(2) 166(3) 4_575 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.55 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.264 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.047 _database_code_depnum_ccdc_archive 'CCDC 945969' ####################################################################### # # 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_COMP6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H8 O5 P, 0.5(C10 H10 N2)' _chemical_formula_sum 'C13 H13 N O5 P' _chemical_formula_weight 294.21 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' 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 monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.995(5) _cell_length_b 11.763(2) _cell_length_c 9.2980(19) _cell_angle_alpha 90.00 _cell_angle_beta 96.14(1) _cell_angle_gamma 90.00 _cell_volume 2500.6(9) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1282 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 29.04 _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas 1.56 _exptl_crystal_density_diffrn 1.563 _exptl_crystal_density_method floatation _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 0.240 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9208 _exptl_absorpt_correction_T_max 0.9558 _exptl_absorpt_process_details ; CrysAlis Red, Version 171.32.6, Oxford Diffraction Poland, 2008 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'KUMA KM-4 with area CCD detector' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16883 _diffrn_reflns_av_R_equivalents 0.0211 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 29.04 _reflns_number_total 3221 _reflns_number_gt 2597 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlis CCD, Version 171.32.6, Oxford Diffraction Poland, 2008 ; _computing_cell_refinement ; CrysAlis Red, Version 171.32.6, Oxford Diffraction Poland, 2008 ; _computing_data_reduction ; CrysAlis Red, Version 171.32.6, Oxford Diffraction Poland, 2008 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Brandenburg & Putz (2006). Diamond 3.0. Crystal and Molecular Structure Visualisation, University of Bonn, Germany ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0488P)^2^+1.8994P] 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 0.0030(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3221 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0473 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0913 _refine_ls_wR_factor_gt 0.0790 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 0.23576(6) 0.03715(12) 0.80415(14) 0.0276(3) Uani 1 1 d . . . C2 C 0.26456(6) -0.05024(11) 0.88450(14) 0.0250(3) Uani 1 1 d . . . H2 H 0.2523 -0.1251 0.8694 0.030 Uiso 1 1 calc R . . C3 C 0.31136(6) -0.02603(11) 0.98675(14) 0.0251(3) Uani 1 1 d . . . C4 C 0.32989(7) 0.08592(12) 1.00938(17) 0.0343(3) Uani 1 1 d . . . H4 H 0.3614 0.1021 1.0777 0.041 Uiso 1 1 calc R . . C5 C 0.30168(7) 0.17237(13) 0.9308(2) 0.0438(4) Uani 1 1 d . . . H5 H 0.3141 0.2471 0.9455 0.053 Uiso 1 1 calc R . . C6 C 0.25499(7) 0.14806(13) 0.83020(18) 0.0383(4) Uani 1 1 d . . . H6 H 0.2358 0.2072 0.7784 0.046 Uiso 1 1 calc R . . C7 C 0.18638(6) 0.01451(14) 0.68813(15) 0.0331(3) Uani 1 1 d . . . H7A H 0.1979 -0.0484 0.6299 0.050 Uiso 1 1 calc R . . H7B H 0.1823 0.0808 0.6258 0.050 Uiso 1 1 calc R . . P1 P 0.115027(15) -0.01815(3) 0.74237(3) 0.02305(11) Uani 1 1 d . . . O1 O 0.11245(5) -0.13389(8) 0.80689(12) 0.0371(3) Uani 1 1 d . . . O2 O 0.07283(4) 0.00156(8) 0.60755(10) 0.0275(2) Uani 1 1 d . . . O3 O 0.10308(5) 0.07667(8) 0.85622(11) 0.0310(2) Uani 1 1 d . . . H3O H 0.0933(8) 0.0500(17) 0.932(2) 0.046 Uiso 1 1 d . . . C8 C 0.34413(6) -0.11616(11) 1.07354(14) 0.0266(3) Uani 1 1 d . . . O4 O 0.38460(5) -0.09384(9) 1.16354(12) 0.0393(3) Uani 1 1 d . . . O5 O 0.32681(5) -0.22091(9) 1.04161(12) 0.0365(3) Uani 1 1 d . . . H5O H 0.3480(9) -0.2695(18) 1.098(2) 0.055 Uiso 1 1 d . . . C9 C 0.00671(5) 0.43861(10) 0.51419(14) 0.0217(3) Uani 1 1 d . . . C10 C 0.04862(6) 0.40534(11) 0.62591(15) 0.0282(3) Uani 1 1 d . . . H10 H 0.0681 0.4597 0.6858 0.034 Uiso 1 1 calc R . . C11 C 0.06105(6) 0.29189(12) 0.64712(15) 0.0315(3) Uani 1 1 d . . . H11 H 0.0890 0.2701 0.7217 0.038 Uiso 1 1 calc R . . N1 N 0.03369(5) 0.21246(9) 0.56279(13) 0.0295(3) Uani 1 1 d . . . H1N H 0.0450(7) 0.1380(15) 0.5801(18) 0.035 Uiso 1 1 d . . . C12 C -0.00687(6) 0.24054(12) 0.45564(17) 0.0330(3) Uani 1 1 d . . . H12 H -0.0254 0.1840 0.3977 0.040 Uiso 1 1 calc R . . C13 C -0.02160(6) 0.35313(11) 0.42994(15) 0.0300(3) Uani 1 1 d . . . H13 H -0.0505 0.3719 0.3561 0.036 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 C1 0.0254(6) 0.0318(7) 0.0254(6) 0.0040(5) 0.0020(5) 0.0042(5) C2 0.0256(6) 0.0224(6) 0.0261(6) 0.0006(5) -0.0018(5) 0.0002(5) C3 0.0235(6) 0.0242(6) 0.0271(6) 0.0013(5) 0.0003(5) 0.0003(5) C4 0.0339(7) 0.0272(7) 0.0398(8) -0.0013(6) -0.0051(6) -0.0043(6) C5 0.0490(9) 0.0283(7) 0.0525(11) 0.0036(7) -0.0016(8) -0.0039(7) C6 0.0404(8) 0.0278(7) 0.0457(9) 0.0113(6) -0.0002(7) 0.0073(6) C7 0.0295(7) 0.0440(8) 0.0247(7) 0.0071(6) -0.0019(5) 0.0063(6) P1 0.02809(18) 0.01897(16) 0.02061(17) 0.00337(12) -0.00421(12) 0.00461(12) O1 0.0480(6) 0.0230(5) 0.0382(6) 0.0092(4) -0.0046(5) 0.0058(4) O2 0.0307(5) 0.0254(5) 0.0241(5) 0.0015(4) -0.0079(4) 0.0044(4) O3 0.0435(6) 0.0237(5) 0.0254(5) 0.0008(4) 0.0024(4) 0.0023(4) C8 0.0240(6) 0.0282(7) 0.0265(7) 0.0018(5) -0.0023(5) -0.0003(5) O4 0.0355(6) 0.0385(6) 0.0395(6) 0.0033(5) -0.0166(5) -0.0016(4) O5 0.0379(6) 0.0246(5) 0.0432(6) 0.0049(4) -0.0139(5) 0.0017(4) C9 0.0214(6) 0.0184(6) 0.0248(6) 0.0017(5) 0.0001(5) 0.0023(5) C10 0.0317(7) 0.0215(6) 0.0290(7) -0.0007(5) -0.0080(5) 0.0021(5) C11 0.0342(7) 0.0254(7) 0.0322(7) 0.0031(5) -0.0082(6) 0.0056(5) N1 0.0318(6) 0.0211(5) 0.0345(7) 0.0021(5) -0.0010(5) 0.0043(4) C12 0.0351(7) 0.0248(6) 0.0367(8) -0.0026(6) -0.0075(6) -0.0006(5) C13 0.0297(7) 0.0237(6) 0.0334(7) 0.0001(5) -0.0111(6) 0.0020(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.391(2) . ? C1 C2 1.3956(18) . ? C1 C7 1.5039(19) . ? C2 C3 1.3872(18) . ? C2 H2 0.9300 . ? C3 C4 1.3931(19) . ? C3 C8 1.4876(18) . ? C4 C5 1.374(2) . ? C4 H4 0.9300 . ? C5 C6 1.376(2) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 P1 1.8087(15) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? P1 O1 1.4915(10) . ? P1 O2 1.5186(10) . ? P1 O3 1.5819(10) . ? O3 H3O 0.83(2) . ? C8 O4 1.2118(16) . ? C8 O5 1.3191(17) . ? O5 H5O 0.88(2) . ? C9 C13 1.3925(18) . ? C9 C10 1.3953(18) . ? C9 C9 1.494(2) 5_566 ? C10 C11 1.3746(18) . ? C10 H10 0.9300 . ? C11 N1 1.3335(18) . ? C11 H11 0.9300 . ? N1 C12 1.3314(19) . ? N1 H1N 0.923(18) . ? C12 C13 1.3815(19) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? 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 C6 C1 C2 118.29(13) . . ? C6 C1 C7 119.52(13) . . ? C2 C1 C7 122.16(13) . . ? C3 C2 C1 120.31(12) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 119.99(12) . . ? C2 C3 C8 122.44(12) . . ? C4 C3 C8 117.56(12) . . ? C5 C4 C3 119.99(14) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 119.82(14) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C1 121.59(13) . . ? C5 C6 H6 119.2 . . ? C1 C6 H6 119.2 . . ? C1 C7 P1 118.39(10) . . ? C1 C7 H7A 107.7 . . ? P1 C7 H7A 107.7 . . ? C1 C7 H7B 107.7 . . ? P1 C7 H7B 107.7 . . ? H7A C7 H7B 107.1 . . ? O1 P1 O2 114.96(6) . . ? O1 P1 O3 110.93(6) . . ? O2 P1 O3 107.66(6) . . ? O1 P1 C7 112.48(7) . . ? O2 P1 C7 104.83(6) . . ? O3 P1 C7 105.33(7) . . ? P1 O3 H3O 112.8(14) . . ? O4 C8 O5 123.29(12) . . ? O4 C8 C3 121.82(13) . . ? O5 C8 C3 114.86(11) . . ? C8 O5 H5O 109.7(13) . . ? C13 C9 C10 117.41(11) . . ? C13 C9 C9 121.55(14) . 5_566 ? C10 C9 C9 121.04(14) . 5_566 ? C11 C10 C9 119.71(12) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? N1 C11 C10 121.21(12) . . ? N1 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C12 N1 C11 120.98(12) . . ? C12 N1 H1N 121.9(11) . . ? C11 N1 H1N 117.1(11) . . ? N1 C12 C13 120.43(13) . . ? N1 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C12 C13 C9 120.25(12) . . ? C12 C13 H13 119.9 . . ? C9 C13 H13 119.9 . . ? 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 N1 H1N O2 0.923(18) 1.736(18) 2.6566(15) 174.5(16) . O3 H3O O2 0.83(2) 1.85(2) 2.6720(15) 177(2) 6_556 O5 H5O O1 0.88(2) 1.65(2) 2.5360(15) 176(2) 7_547 _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.290 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.047 _database_code_depnum_ccdc_archive 'CCDC 945970'