# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email wlin@email.unc.edu _publ_contact_author_name 'Wenbin Lin' loop_ _publ_author_name 'Wenbin Lin' 'Demin Liu' S.Kramer R.Huxford 'Shunzhi Wang' J.D.Rocca data_pna21 _database_code_depnum_ccdc_archive 'CCDC 856980' #TrackingRef 'web_deposit_cif_file_0_DeminLiu_1323120528.Ca_Pam.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H7 Ca N O9 P2' _chemical_formula_weight 303.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ca Ca 0.3641 1.2855 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna21 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' _cell_length_a 13.7486(3) _cell_length_b 10.6087(2) _cell_length_c 6.9230(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1009.75(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.994 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 8.811 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.0412 _exptl_absorpt_correction_T_max 0.8435 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3572 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0421 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 5.27 _diffrn_reflns_theta_max 69.30 _reflns_number_total 1472 _reflns_number_gt 1437 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0540P)^2^+1.3845P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.052(19) _refine_ls_number_reflns 1472 _refine_ls_number_parameters 154 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0960 _refine_ls_wR_factor_gt 0.0954 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.103 _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 Ca1 Ca -0.02351(6) 0.07730(7) 1.37438(15) 0.0095(2) Uani 1 1 d . . . P2 P -0.02291(7) 0.20366(9) 0.8755(2) 0.0086(3) Uani 1 1 d . . . P1 P 0.16584(7) 0.16170(10) 0.67406(19) 0.0104(3) Uani 1 1 d . . . C3 C 0.1517(3) 0.3064(5) 1.0072(8) 0.0164(10) Uani 1 1 d . . . H3A H 0.2188 0.3336 0.9765 0.020 Uiso 1 1 calc R . . H3B H 0.1556 0.2292 1.0872 0.020 Uiso 1 1 calc R . . O3 O 0.2730(2) 0.2133(3) 0.6597(6) 0.0160(7) Uani 1 1 d . . . O4 O 0.1641(2) 0.0355(3) 0.7760(5) 0.0140(7) Uani 1 1 d . . . O5 O 0.1267(2) 0.1661(3) 0.4694(5) 0.0157(8) Uani 1 1 d . . . O6 O -0.0505(2) 0.1201(3) 0.7052(5) 0.0102(6) Uani 1 1 d . . . O7 O -0.0981(2) 0.3083(3) 0.9129(5) 0.0122(7) Uani 1 1 d . . . O8 O -0.0029(2) 0.1213(3) 1.0494(5) 0.0113(7) Uani 1 1 d . . . C2 C 0.0979(3) 0.2774(4) 0.8220(7) 0.0121(10) Uani 1 1 d . . . O9 O -0.1167(3) 0.2646(3) 1.3314(6) 0.0247(9) Uani 1 1 d . . . O10 O 0.0832(3) 0.3899(3) 0.7092(6) 0.0208(8) Uani 1 1 d . . . H10 H 0.1182 0.4482 0.7530 0.031 Uiso 1 1 calc R . . C4 C 0.0985(4) 0.4133(5) 1.1243(9) 0.0264(13) Uani 1 1 d . . . H4A H 0.1001 0.4930 1.0498 0.032 Uiso 1 1 calc R . . H4B H 0.0296 0.3898 1.1447 0.032 Uiso 1 1 calc R . . N1 N 0.1469(3) 0.4321(5) 1.3142(7) 0.0258(11) Uani 1 1 d . . . H1A H 0.1977 0.3860 1.3457 0.031 Uiso 1 1 calc R . . H1B H 0.1247 0.4892 1.3952 0.031 Uiso 1 1 calc R . . O11 O 0.2602(3) 0.5123(4) 0.7153(8) 0.0384(11) Uani 1 1 d D . . H11 H 0.310(5) 0.560(7) 0.792(12) 0.06(3) Uiso 1 1 d D . . H11B H 0.200(4) 0.466(7) 0.679(15) 0.06(2) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ca1 0.0096(4) 0.0120(4) 0.0069(4) 0.0001(4) -0.0003(3) -0.0006(3) P2 0.0076(4) 0.0100(5) 0.0082(6) -0.0008(5) 0.0001(4) -0.0002(4) P1 0.0076(5) 0.0158(5) 0.0079(6) 0.0003(5) -0.0001(4) -0.0024(4) C3 0.009(2) 0.022(3) 0.018(3) 0.001(2) -0.003(2) -0.0052(17) O3 0.0118(15) 0.0244(17) 0.0119(17) 0.0003(15) 0.0007(14) -0.0045(11) O4 0.0096(14) 0.0163(16) 0.0161(19) 0.0011(14) 0.0007(12) -0.0003(11) O5 0.0115(15) 0.0257(19) 0.0100(19) -0.0009(14) 0.0017(14) -0.0050(12) O6 0.0085(13) 0.0127(14) 0.0095(18) -0.0013(13) 0.0030(13) -0.0006(11) O7 0.0130(15) 0.0127(14) 0.011(2) -0.0018(12) -0.0004(13) 0.0023(11) O8 0.0098(13) 0.0134(15) 0.0105(19) 0.0006(14) -0.0015(13) -0.0002(12) C2 0.0111(19) 0.012(2) 0.014(3) -0.0008(17) 0.0036(18) -0.0027(16) O9 0.0333(18) 0.0235(18) 0.017(2) 0.0014(15) 0.0074(17) 0.0118(15) O10 0.0224(17) 0.0158(16) 0.024(2) 0.0037(15) 0.0001(17) -0.0020(13) C4 0.020(2) 0.031(3) 0.028(4) -0.007(2) 0.001(2) -0.003(2) N1 0.026(2) 0.027(2) 0.024(3) -0.0053(18) 0.002(2) 0.0001(18) O11 0.029(2) 0.038(2) 0.049(3) -0.003(2) 0.001(2) -0.0091(17) _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 Ca1 O8 2.315(4) . ? Ca1 O5 2.364(3) 1_556 ? Ca1 O6 2.364(4) 1_556 ? Ca1 O4 2.373(3) 2 ? Ca1 O9 2.383(3) . ? Ca1 O8 2.458(3) 2 ? Ca1 O6 2.606(3) 2 ? Ca1 P2 3.0482(12) 2 ? Ca1 P1 3.4472(14) 1_556 ? Ca1 P1 3.4901(14) 2 ? Ca1 Ca1 3.8846(7) 2 ? Ca1 Ca1 3.8846(7) 2_554 ? P2 O8 1.513(4) . ? P2 O6 1.523(3) . ? P2 O7 1.539(3) . ? P2 C2 1.873(4) . ? P2 Ca1 3.0482(12) 2_554 ? P1 O4 1.513(3) . ? P1 O5 1.516(4) . ? P1 O3 1.575(3) . ? P1 C2 1.852(5) . ? P1 Ca1 3.4472(14) 1_554 ? P1 Ca1 3.4901(14) 2_554 ? C3 C2 1.511(7) . ? C3 C4 1.575(7) . ? O4 Ca1 2.373(3) 2_554 ? O5 Ca1 2.364(3) 1_554 ? O6 Ca1 2.364(4) 1_554 ? O6 Ca1 2.606(3) 2_554 ? O8 Ca1 2.458(3) 2_554 ? C2 O10 1.440(6) . ? C4 N1 1.487(8) . ? 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 O8 Ca1 O5 94.76(12) . 1_556 ? O8 Ca1 O6 157.19(10) . 1_556 ? O5 Ca1 O6 77.94(12) 1_556 1_556 ? O8 Ca1 O4 85.56(13) . 2 ? O5 Ca1 O4 173.03(12) 1_556 2 ? O6 Ca1 O4 104.31(12) 1_556 2 ? O8 Ca1 O9 77.07(13) . . ? O5 Ca1 O9 99.92(13) 1_556 . ? O6 Ca1 O9 82.90(13) 1_556 . ? O4 Ca1 O9 86.95(13) 2 . ? O8 Ca1 O8 129.35(10) . 2 ? O5 Ca1 O8 94.33(12) 1_556 2 ? O6 Ca1 O8 73.16(11) 1_556 2 ? O4 Ca1 O8 80.18(12) 2 2 ? O9 Ca1 O8 148.86(13) . 2 ? O8 Ca1 O6 71.21(11) . 2 ? O5 Ca1 O6 95.98(11) 1_556 2 ? O6 Ca1 O6 130.61(10) 1_556 2 ? O4 Ca1 O6 77.50(10) 2 2 ? O9 Ca1 O6 145.47(13) . 2 ? O8 Ca1 O6 58.32(10) 2 2 ? O8 Ca1 P2 100.04(8) . 2 ? O5 Ca1 P2 101.90(9) 1_556 2 ? O6 Ca1 P2 102.60(8) 1_556 2 ? O4 Ca1 P2 71.22(8) 2 2 ? O9 Ca1 P2 158.16(10) . 2 ? O8 Ca1 P2 29.48(9) 2 2 ? O6 Ca1 P2 29.96(8) 2 2 ? O8 Ca1 P1 116.11(9) . 1_556 ? O5 Ca1 P1 21.42(9) 1_556 1_556 ? O6 Ca1 P1 59.04(8) 1_556 1_556 ? O4 Ca1 P1 156.74(10) 2 1_556 ? O9 Ca1 P1 105.35(11) . 1_556 ? O8 Ca1 P1 79.30(9) 2 1_556 ? O6 Ca1 P1 100.62(8) 2 1_556 ? P2 Ca1 P1 95.41(4) 2 1_556 ? O8 Ca1 P1 80.16(8) . 2 ? O5 Ca1 P1 152.89(9) 1_556 2 ? O6 Ca1 P1 115.89(8) 1_556 2 ? O4 Ca1 P1 20.44(8) 2 2 ? O9 Ca1 P1 104.75(10) . 2 ? O8 Ca1 P1 69.88(8) 2 2 ? O6 Ca1 P1 57.08(7) 2 2 ? P2 Ca1 P1 53.70(3) 2 2 ? P1 Ca1 P1 148.35(3) 1_556 2 ? O8 Ca1 Ca1 158.56(9) . 2 ? O5 Ca1 Ca1 77.00(9) 1_556 2 ? O6 Ca1 Ca1 40.89(7) 1_556 2 ? O4 Ca1 Ca1 100.27(10) 2 2 ? O9 Ca1 Ca1 123.56(10) . 2 ? O8 Ca1 Ca1 34.31(9) 2 2 ? O6 Ca1 Ca1 89.77(8) 2 2 ? P2 Ca1 Ca1 63.26(4) 2 2 ? P1 Ca1 Ca1 56.47(3) 1_556 2 ? P1 Ca1 Ca1 98.09(4) 2 2 ? O8 Ca1 Ca1 36.77(8) . 2_554 ? O5 Ca1 Ca1 105.71(9) 1_556 2_554 ? O6 Ca1 Ca1 166.04(8) 1_556 2_554 ? O4 Ca1 Ca1 70.54(9) 2 2_554 ? O9 Ca1 Ca1 109.29(11) . 2_554 ? O8 Ca1 Ca1 93.03(9) 2 2_554 ? O6 Ca1 Ca1 36.43(8) 2 2_554 ? P2 Ca1 Ca1 63.55(4) 2 2_554 ? P1 Ca1 Ca1 121.35(4) 1_556 2_554 ? P1 Ca1 Ca1 55.42(3) 2 2_554 ? Ca1 Ca1 Ca1 126.02(4) 2 2_554 ? O8 P2 O6 109.00(17) . . ? O8 P2 O7 113.9(2) . . ? O6 P2 O7 112.50(19) . . ? O8 P2 C2 103.7(2) . . ? O6 P2 C2 108.1(2) . . ? O7 P2 C2 109.12(18) . . ? O8 P2 Ca1 53.09(13) . 2_554 ? O6 P2 Ca1 58.74(12) . 2_554 ? O7 P2 Ca1 147.84(13) . 2_554 ? C2 P2 Ca1 102.84(14) . 2_554 ? O4 P1 O5 117.2(2) . . ? O4 P1 O3 110.58(18) . . ? O5 P1 O3 105.2(2) . . ? O4 P1 C2 108.7(2) . . ? O5 P1 C2 108.5(2) . . ? O3 P1 C2 106.05(19) . . ? O4 P1 Ca1 92.23(13) . 1_554 ? O5 P1 Ca1 34.70(13) . 1_554 ? O3 P1 Ca1 139.35(16) . 1_554 ? C2 P1 Ca1 97.15(15) . 1_554 ? O4 P1 Ca1 33.20(12) . 2_554 ? O5 P1 Ca1 101.25(13) . 2_554 ? O3 P1 Ca1 143.32(14) . 2_554 ? C2 P1 Ca1 88.81(14) . 2_554 ? Ca1 P1 Ca1 68.10(2) 1_554 2_554 ? C2 C3 C4 110.8(4) . . ? P1 O4 Ca1 126.36(18) . 2_554 ? P1 O5 Ca1 123.87(19) . 1_554 ? P2 O6 Ca1 145.36(18) . 1_554 ? P2 O6 Ca1 91.30(16) . 2_554 ? Ca1 O6 Ca1 102.68(11) 1_554 2_554 ? P2 O8 Ca1 150.2(2) . . ? P2 O8 Ca1 97.43(18) . 2_554 ? Ca1 O8 Ca1 108.92(12) . 2_554 ? O10 C2 C3 111.1(4) . . ? O10 C2 P1 108.7(3) . . ? C3 C2 P1 110.9(3) . . ? O10 C2 P2 109.2(3) . . ? C3 C2 P2 110.5(3) . . ? P1 C2 P2 106.2(2) . . ? N1 C4 C3 110.1(5) . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 69.30 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.626 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.110 # Attachment 'web_deposit_cif_file_1_DeminLiu_1323120528.Ca_Zol.cif' data_ca_zol _database_code_depnum_ccdc_archive 'CCDC 856981' #TrackingRef 'web_deposit_cif_file_1_DeminLiu_1323120528.Ca_Zol.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6.67 H8 Ca1.33 N2.67 O10.67 P2.67' _chemical_formula_weight 432.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ca Ca 0.3641 1.2855 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pna2(1) ' 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' _cell_length_a 13.4828(9) _cell_length_b 12.6963(7) _cell_length_c 6.7635(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1157.79(13) _cell_formula_units_Z 3 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.860 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 7.701 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5131 _exptl_absorpt_correction_T_max 0.9270 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4056 _diffrn_reflns_av_R_equivalents 0.0841 _diffrn_reflns_av_sigmaI/netI 0.0820 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 4.78 _diffrn_reflns_theta_max 54.06 _reflns_number_total 1107 _reflns_number_gt 916 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0949P)^2^+1.0320P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(4) _refine_ls_number_reflns 1107 _refine_ls_number_parameters 164 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0776 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.1518 _refine_ls_wR_factor_gt 0.1434 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.083 _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 Ca1 Ca -0.03772(14) 0.05477(16) 0.7367(4) 0.0170(6) Uani 1 1 d . . . P2 P 0.06046(19) -0.1613(2) 0.7353(5) 0.0164(7) Uani 1 1 d . . . P3 P 0.1358(2) 0.1768(2) 1.0226(5) 0.0181(8) Uani 1 1 d . . . O2 O -0.0192(5) 0.1029(6) 0.4142(12) 0.0160(18) Uani 1 1 d . . . O5 O -0.0759(5) 0.0854(6) 1.0643(12) 0.017(2) Uani 1 1 d . . . O1 O 0.0976(5) 0.1639(6) 0.8170(11) 0.022(2) Uani 1 1 d . . . O3 O -0.1564(6) -0.0752(6) 0.6367(12) 0.019(2) Uani 1 1 d . . . O4 O -0.1594(7) 0.1901(6) 0.6947(13) 0.033(2) Uani 1 1 d . . . O6 O 0.2318(5) 0.2474(6) 1.0161(13) 0.0225(18) Uani 1 1 d . . . O7 O 0.1506(5) -0.2297(5) 0.7877(11) 0.0160(19) Uani 1 1 d . . . C1 C 0.0423(9) 0.2498(9) 1.1664(19) 0.024(3) Uani 1 1 d . . . O9 O 0.0899(7) 0.2839(8) 1.3579(15) 0.046(3) Uani 1 1 d . . . H9 H 0.0827 0.3492 1.3723 0.069 Uiso 1 1 calc R . . C3 C 0.0042(11) 0.3417(11) 1.059(3) 0.055(3) Uani 1 1 d U . . H3A H -0.0526 0.3718 1.1321 0.066 Uiso 1 1 calc R . . H3B H -0.0201 0.3188 0.9274 0.066 Uiso 1 1 calc R . . N1 N 0.0860(9) 0.4295(10) 1.030(2) 0.055(3) Uani 1 1 d U . . C4 C 0.1312(12) 0.4871(11) 1.167(3) 0.056(5) Uani 1 1 d . . . H4 H 0.1153 0.4905 1.3037 0.068 Uiso 1 1 calc R . . C5 C 0.1282(11) 0.4383(11) 0.843(3) 0.049(5) Uani 1 1 d . . . H5 H 0.1105 0.4026 0.7242 0.059 Uiso 1 1 calc R . . N2 N 0.2028(9) 0.5129(10) 0.873(2) 0.059(4) Uani 1 1 d . . . C6 C 0.2053(11) 0.5405(12) 1.072(3) 0.055(5) Uani 1 1 d . . . H6 H 0.2506 0.5883 1.1310 0.066 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 Ca1 0.0161(10) 0.0190(13) 0.0158(13) 0.0005(12) -0.0015(13) 0.0009(9) P2 0.0188(15) 0.0166(15) 0.0138(17) 0.0010(16) 0.0027(15) -0.0002(11) P3 0.0161(14) 0.0195(17) 0.0186(19) -0.0001(15) 0.0003(14) -0.0050(13) O2 0.017(4) 0.015(4) 0.016(5) 0.006(4) 0.001(4) 0.002(4) O5 0.015(4) 0.017(5) 0.020(5) -0.001(4) -0.004(4) -0.005(3) O1 0.017(4) 0.038(5) 0.011(5) -0.002(4) 0.002(3) -0.008(4) O3 0.022(4) 0.018(5) 0.017(5) -0.013(4) -0.004(4) 0.000(3) O4 0.050(5) 0.028(5) 0.020(6) -0.002(4) 0.009(4) 0.017(4) O6 0.018(4) 0.026(5) 0.024(5) 0.003(4) 0.005(4) -0.003(3) O7 0.021(4) 0.011(4) 0.016(5) 0.002(3) 0.003(4) 0.008(3) C1 0.040(8) 0.010(7) 0.022(8) -0.004(5) 0.008(6) 0.004(6) O9 0.051(6) 0.045(6) 0.042(7) -0.030(5) 0.005(5) -0.009(6) C3 0.048(6) 0.058(7) 0.059(8) 0.024(6) 0.031(6) 0.010(5) N1 0.048(6) 0.058(7) 0.059(8) 0.023(6) 0.031(6) 0.009(5) C4 0.068(11) 0.052(11) 0.049(12) -0.041(9) 0.022(9) -0.023(9) C5 0.043(10) 0.043(10) 0.061(13) 0.000(8) -0.010(8) 0.022(8) N2 0.057(9) 0.033(8) 0.088(14) 0.011(8) -0.001(8) 0.002(6) C6 0.048(10) 0.048(11) 0.068(14) -0.024(9) 0.029(9) -0.026(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ca1 O2 2.279(8) . ? Ca1 O5 2.308(9) . ? Ca1 O1 2.355(8) . ? Ca1 O4 2.393(8) . ? Ca1 O3 2.395(8) . ? Ca1 O2 2.457(8) 2 ? Ca1 O5 2.622(8) 2_554 ? Ca1 P3 3.535(4) 2_554 ? Ca1 Ca1 3.7954(18) 2 ? Ca1 Ca1 3.7954(18) 2_554 ? P2 O5 1.520(8) 2_554 ? P2 O2 1.525(8) 2 ? P2 O7 1.535(7) . ? P2 C1 1.843(12) 2_554 ? P3 O1 1.492(8) . ? P3 O3 1.529(8) 2 ? P3 O6 1.575(7) . ? P3 C1 1.842(13) . ? P3 Ca1 3.535(4) 2 ? O2 P2 1.525(8) 2_554 ? O2 Ca1 2.457(8) 2_554 ? O5 P2 1.520(8) 2 ? O5 Ca1 2.622(8) 2 ? O3 P3 1.529(8) 2_554 ? C1 C3 1.468(18) . ? C1 O9 1.509(15) . ? C1 P2 1.843(12) 2 ? C3 N1 1.580(19) . ? N1 C4 1.33(2) . ? N1 C5 1.39(2) . ? C4 C6 1.37(2) . ? C5 N2 1.397(19) . ? N2 C6 1.39(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 Ca1 O5 153.9(3) . . ? O2 Ca1 O1 88.8(3) . . ? O5 Ca1 O1 81.5(3) . . ? O2 Ca1 O4 76.7(3) . . ? O5 Ca1 O4 80.8(3) . . ? O1 Ca1 O4 97.8(3) . . ? O2 Ca1 O3 89.3(3) . . ? O5 Ca1 O3 103.8(3) . . ? O1 Ca1 O3 171.1(3) . . ? O4 Ca1 O3 90.2(3) . . ? O2 Ca1 O2 130.7(2) . 2 ? O5 Ca1 O2 74.8(3) . 2 ? O1 Ca1 O2 97.1(3) . 2 ? O4 Ca1 O2 149.0(3) . 2 ? O3 Ca1 O2 77.6(3) . 2 ? O2 Ca1 O5 72.1(3) . 2_554 ? O5 Ca1 O5 132.2(3) . 2_554 ? O1 Ca1 O5 92.8(2) . 2_554 ? O4 Ca1 O5 146.7(3) . 2_554 ? O3 Ca1 O5 78.3(2) . 2_554 ? O2 Ca1 O5 58.8(2) 2 2_554 ? O2 Ca1 P3 82.6(2) . 2_554 ? O5 Ca1 P3 116.7(2) . 2_554 ? O1 Ca1 P3 150.9(2) . 2_554 ? O4 Ca1 P3 107.0(2) . 2_554 ? O3 Ca1 P3 20.19(19) . 2_554 ? O2 Ca1 P3 68.87(19) 2 2_554 ? O5 Ca1 P3 58.12(17) 2_554 2_554 ? O2 Ca1 Ca1 157.2(2) . 2 ? O5 Ca1 Ca1 42.78(19) . 2 ? O1 Ca1 Ca1 78.6(2) . 2 ? O4 Ca1 Ca1 123.5(2) . 2 ? O3 Ca1 Ca1 100.3(2) . 2 ? O2 Ca1 Ca1 35.15(19) 2 2 ? O5 Ca1 Ca1 89.5(2) 2_554 2 ? P3 Ca1 Ca1 99.24(10) 2_554 2 ? O2 Ca1 Ca1 38.37(18) . 2_554 ? O5 Ca1 Ca1 167.7(2) . 2_554 ? O1 Ca1 Ca1 102.3(2) . 2_554 ? O4 Ca1 Ca1 110.0(2) . 2_554 ? O3 Ca1 Ca1 71.0(2) . 2_554 ? O2 Ca1 Ca1 93.1(2) 2 2_554 ? O5 Ca1 Ca1 36.71(19) 2_554 2_554 ? P3 Ca1 Ca1 55.28(8) 2_554 2_554 ? Ca1 Ca1 Ca1 126.00(10) 2 2_554 ? O5 P2 O2 110.2(4) 2_554 2 ? O5 P2 O7 115.2(4) 2_554 . ? O2 P2 O7 112.4(5) 2 . ? O5 P2 C1 107.3(5) 2_554 2_554 ? O2 P2 C1 102.9(5) 2 2_554 ? O7 P2 C1 108.0(5) . 2_554 ? O1 P3 O3 116.1(5) . 2 ? O1 P3 O6 108.7(5) . . ? O3 P3 O6 110.2(4) 2 . ? O1 P3 C1 108.1(5) . . ? O3 P3 C1 106.3(5) 2 . ? O6 P3 C1 106.9(5) . . ? O1 P3 Ca1 99.3(3) . 2 ? O3 P3 Ca1 32.7(3) 2 2 ? O6 P3 Ca1 142.4(3) . 2 ? C1 P3 Ca1 86.9(4) . 2 ? P2 O2 Ca1 148.2(5) 2_554 . ? P2 O2 Ca1 97.0(4) 2_554 2_554 ? Ca1 O2 Ca1 106.5(3) . 2_554 ? P2 O5 Ca1 143.8(5) 2 . ? P2 O5 Ca1 90.7(4) 2 2 ? Ca1 O5 Ca1 100.5(3) . 2 ? P3 O1 Ca1 123.2(4) . . ? P3 O3 Ca1 127.1(5) 2_554 . ? C3 C1 O9 110.3(11) . . ? C3 C1 P2 110.3(10) . 2 ? O9 C1 P2 106.1(8) . 2 ? C3 C1 P3 112.1(10) . . ? O9 C1 P3 107.8(8) . . ? P2 C1 P3 110.0(6) 2 . ? C1 C3 N1 112.2(12) . . ? C4 N1 C5 113.8(14) . . ? C4 N1 C3 128.6(15) . . ? C5 N1 C3 116.9(15) . . ? N1 C4 C6 106.2(14) . . ? N1 C5 N2 102.4(14) . . ? C6 N2 C5 109.2(14) . . ? C4 C6 N2 108.3(14) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 54.06 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.666 _refine_diff_density_min -0.476 _refine_diff_density_rms 0.121