# Electronic Supplementary Material (ESI) for Chemical Science # 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_1 _database_code_depnum_ccdc_archive 'CCDC 882458' #TrackingRef '- 6-LXQ101210.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H16 Ca N O7 P, H O0.50, H O0.50' _chemical_formula_sum 'C7 H18 Ca N O8 P' _chemical_formula_weight 315.27 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 Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.8101(3) _cell_length_b 9.5015(4) _cell_length_c 21.2601(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1375.66(9) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 4738 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 26.92 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.522 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.602 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8495 _exptl_absorpt_correction_T_max 0.8689 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15188 _diffrn_reflns_av_R_equivalents 0.0551 _diffrn_reflns_av_sigmaI/netI 0.0812 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2711 _reflns_number_gt 2121 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+1.2200P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(7) _chemical_absolute_configuration unk _refine_ls_number_reflns 2711 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0720 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1072 _refine_ls_wR_factor_gt 0.1050 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 0.6408(8) 0.9219(5) 0.4315(2) 0.0316(10) Uani 1 1 d . . . C2 C 0.6125(6) 0.7760(5) 0.4048(2) 0.0302(10) Uani 1 1 d . . . H2 H 0.6894 0.7105 0.4305 0.036 Uiso 1 1 calc R . . C3 C 0.6841(7) 0.7634(5) 0.3370(2) 0.0344(11) Uani 1 1 d . . . H3A H 0.8228 0.7862 0.3350 0.041 Uiso 1 1 calc R . . H3B H 0.6137 0.8300 0.3108 0.041 Uiso 1 1 calc R . . C4 C 0.6512(8) 0.6144(5) 0.3123(2) 0.0369(12) Uani 1 1 d . . . H4A H 0.6921 0.6094 0.2687 0.044 Uiso 1 1 calc R . . H4B H 0.7311 0.5489 0.3362 0.044 Uiso 1 1 calc R . . C5 C 0.3978(6) 0.7321(4) 0.4090(2) 0.0291(10) Uani 1 1 d . . . H5A H 0.3542 0.7364 0.4524 0.035 Uiso 1 1 calc R . . H5B H 0.3176 0.7961 0.3844 0.035 Uiso 1 1 calc R . . C6 C 0.4407(7) 0.5731(5) 0.3174(2) 0.0314(11) Uani 1 1 d . . . H6A H 0.4239 0.4774 0.3025 0.038 Uiso 1 1 calc R . . H6B H 0.3613 0.6346 0.2913 0.038 Uiso 1 1 calc R . . C7 C 0.1641(8) 0.5315(5) 0.3917(2) 0.0352(10) Uani 1 1 d . . . H7A H 0.0874 0.5588 0.3552 0.042 Uiso 1 1 calc R . . H7B H 0.1054 0.5745 0.4286 0.042 Uiso 1 1 calc R . . Ca1 Ca -0.34730(13) 0.22604(9) 0.45601(4) 0.0243(2) Uani 1 1 d . . . N1 N 0.3741(6) 0.5832(4) 0.38420(16) 0.0269(8) Uani 1 1 d . . . H1 H 0.4527 0.5264 0.4077 0.032 Uiso 1 1 d R . . O1 O -0.0357(5) 0.3042(3) 0.42935(15) 0.0310(8) Uani 1 1 d . . . O2 O 0.3247(5) 0.3126(3) 0.44639(14) 0.0338(8) Uani 1 1 d . . . O3 O 0.1973(4) 0.2737(4) 0.33600(14) 0.0314(7) Uani 1 1 d . . . O4 O 0.4966(5) 0.9877(3) 0.45447(15) 0.0348(8) Uani 1 1 d . . . O5 O 0.8098(5) 0.9764(3) 0.42919(15) 0.0350(8) Uani 1 1 d . . . O1W O -0.4008(5) 0.2258(4) 0.34524(14) 0.0348(8) Uani 1 1 d . . . H1X H -0.2802 0.2028 0.3242 0.042 Uiso 1 1 d R . . H1Y H -0.5351 0.2493 0.3365 0.042 Uiso 1 1 d R . . O2W O -0.3620(6) 0.4752(3) 0.49148(13) 0.0320(7) Uani 1 1 d . . . H2X H -0.4843 0.4919 0.5127 0.038 Uiso 1 1 d R . . H2Y H -0.2552 0.4935 0.5198 0.038 Uiso 1 1 d R . . O3W O 0.8954(9) 0.4846(6) 0.1626(3) 0.0249(14) Uani 0.50 1 d P . . H3X H 0.9332 0.5680 0.1577 0.030 Uiso 0.50 1 d PR . . H3Y H 0.8805 0.4671 0.2018 0.030 Uiso 0.50 1 d PR . . O4W O 0.8780(8) 0.2908(6) 0.2561(2) 0.0240(13) Uani 0.50 1 d P . . H4X H 0.8534 0.3545 0.2291 0.029 Uiso 0.50 1 d PR . . H4Y H 0.9761 0.3136 0.2786 0.029 Uiso 0.50 1 d PR . . P2 P 0.1602(2) 0.33803(12) 0.40007(6) 0.0297(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 C1 0.030(2) 0.030(2) 0.035(2) -0.0017(19) 0.007(2) 0.002(2) C2 0.029(2) 0.031(2) 0.031(2) -0.007(2) 0.0045(19) 0.003(2) C3 0.034(3) 0.031(2) 0.038(2) -0.019(2) 0.012(2) -0.012(2) C4 0.040(3) 0.037(3) 0.034(3) -0.014(2) 0.014(3) -0.013(3) C5 0.027(2) 0.020(2) 0.040(3) -0.010(2) 0.0119(19) -0.0100(18) C6 0.044(3) 0.023(2) 0.028(2) 0.0084(19) 0.006(2) -0.004(2) C7 0.029(2) 0.037(2) 0.040(3) -0.002(2) -0.001(2) 0.002(2) Ca1 0.0254(4) 0.0210(4) 0.0264(4) 0.0001(4) -0.0016(4) -0.0013(4) N1 0.024(2) 0.0253(18) 0.031(2) 0.0029(14) -0.0023(17) 0.0020(17) O1 0.0319(18) 0.0273(18) 0.0338(17) 0.0009(14) 0.0073(14) -0.0043(14) O2 0.0339(18) 0.0356(18) 0.0317(17) -0.0017(13) 0.0018(15) 0.0028(15) O3 0.0290(18) 0.0354(17) 0.0297(16) -0.0011(14) 0.0023(13) 0.0010(15) O4 0.0374(18) 0.0317(18) 0.0352(18) -0.0058(17) 0.0209(16) -0.0104(14) O5 0.038(2) 0.0358(18) 0.0310(16) -0.0096(15) 0.0046(15) -0.0030(16) O1W 0.0317(18) 0.0382(18) 0.0345(17) 0.0001(16) 0.0072(14) 0.0088(15) O2W 0.0345(19) 0.0292(16) 0.0324(17) -0.0006(13) 0.0028(15) 0.0051(17) O3W 0.031(4) 0.016(3) 0.028(3) 0.006(2) -0.001(3) 0.005(2) O4W 0.021(3) 0.029(3) 0.022(3) 0.018(2) 0.002(2) -0.001(3) P2 0.0258(6) 0.0294(6) 0.0339(6) -0.0015(5) 0.0009(6) -0.0025(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 C1 O4 1.262(6) . ? C1 O5 1.263(6) . ? C1 C2 1.510(6) . ? C1 Ca1 2.937(4) 1_665 ? C2 C5 1.523(6) . ? C2 C3 1.526(6) . ? C2 H2 0.9800 . ? C3 C4 1.527(6) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C6 1.491(7) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N1 1.518(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N1 1.494(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N1 1.521(6) . ? C7 P2 1.847(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? Ca1 O1 2.319(3) . ? Ca1 O1W 2.383(3) . ? Ca1 O2 2.389(4) 1_455 ? Ca1 O2 2.411(3) 4_456 ? Ca1 O2W 2.487(3) . ? Ca1 O4 2.502(3) 1_445 ? Ca1 O5 2.664(3) 1_445 ? Ca1 O1 2.769(3) 4_456 ? Ca1 C1 2.937(4) 1_445 ? Ca1 P2 3.1202(14) 4_456 ? Ca1 Ca1 3.9117(8) 4_556 ? Ca1 Ca1 3.9117(8) 4_456 ? N1 H1 0.9100 . ? O1 P2 1.506(3) . ? O1 Ca1 2.769(3) 4_556 ? O2 P2 1.511(4) . ? O2 Ca1 2.389(4) 1_655 ? O2 Ca1 2.411(3) 4_556 ? O3 P2 1.514(3) . ? O4 Ca1 2.502(3) 1_665 ? O5 Ca1 2.664(3) 1_665 ? O1W H1X 0.9601 . ? O1W H1Y 0.9600 . ? O2W H2X 0.9601 . ? O2W H2Y 0.9600 . ? O3W H3X 0.8395 . ? O3W H3Y 0.8560 . ? O4W H4X 0.8500 . ? O4W H4Y 0.8500 . ? P2 Ca1 3.1202(14) 4_556 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 C1 O5 121.4(4) . . ? O4 C1 C2 120.0(5) . . ? O5 C1 C2 118.6(4) . . ? O4 C1 Ca1 57.7(2) . 1_665 ? O5 C1 Ca1 65.1(2) . 1_665 ? C2 C1 Ca1 166.7(3) . 1_665 ? C1 C2 C5 110.6(4) . . ? C1 C2 C3 112.7(4) . . ? C5 C2 C3 109.9(4) . . ? C1 C2 H2 107.8 . . ? C5 C2 H2 107.8 . . ? C3 C2 H2 107.8 . . ? C2 C3 C4 110.5(4) . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C6 C4 C3 111.1(4) . . ? C6 C4 H4A 109.4 . . ? C3 C4 H4A 109.4 . . ? C6 C4 H4B 109.4 . . ? C3 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? N1 C5 C2 109.7(3) . . ? N1 C5 H5A 109.7 . . ? C2 C5 H5A 109.7 . . ? N1 C5 H5B 109.7 . . ? C2 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? C4 C6 N1 110.1(4) . . ? C4 C6 H6A 109.6 . . ? N1 C6 H6A 109.6 . . ? C4 C6 H6B 109.6 . . ? N1 C6 H6B 109.6 . . ? H6A C6 H6B 108.2 . . ? N1 C7 P2 110.2(3) . . ? N1 C7 H7A 109.6 . . ? P2 C7 H7A 109.6 . . ? N1 C7 H7B 109.6 . . ? P2 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? O1 Ca1 O1W 84.18(11) . . ? O1 Ca1 O2 136.43(11) . 1_455 ? O1W Ca1 O2 76.88(11) . 1_455 ? O1 Ca1 O2 79.31(12) . 4_456 ? O1W Ca1 O2 157.61(11) . 4_456 ? O2 Ca1 O2 125.47(9) 1_455 4_456 ? O1 Ca1 O2W 78.82(12) . . ? O1W Ca1 O2W 107.13(11) . . ? O2 Ca1 O2W 70.15(12) 1_455 . ? O2 Ca1 O2W 84.47(10) 4_456 . ? O1 Ca1 O4 132.50(11) . 1_445 ? O1W Ca1 O4 85.48(12) . 1_445 ? O2 Ca1 O4 85.03(11) 1_455 1_445 ? O2 Ca1 O4 94.58(11) 4_456 1_445 ? O2W Ca1 O4 148.06(12) . 1_445 ? O1 Ca1 O5 82.25(11) . 1_445 ? O1W Ca1 O5 81.31(11) . 1_445 ? O2 Ca1 O5 131.60(11) 1_455 1_445 ? O2 Ca1 O5 81.57(10) 4_456 1_445 ? O2W Ca1 O5 158.25(12) . 1_445 ? O4 Ca1 O5 50.35(10) 1_445 1_445 ? O1 Ca1 O1 132.24(9) . 4_456 ? O1W Ca1 O1 143.03(11) . 4_456 ? O2 Ca1 O1 71.22(9) 1_455 4_456 ? O2 Ca1 O1 56.75(10) 4_456 4_456 ? O2W Ca1 O1 79.23(10) . 4_456 ? O4 Ca1 O1 73.79(10) 1_445 4_456 ? O5 Ca1 O1 106.38(10) 1_445 4_456 ? O1 Ca1 C1 107.27(13) . 1_445 ? O1W Ca1 C1 79.60(13) . 1_445 ? O2 Ca1 C1 107.33(13) 1_455 1_445 ? O2 Ca1 C1 90.92(12) 4_456 1_445 ? O2W Ca1 C1 171.60(12) . 1_445 ? O4 Ca1 C1 25.25(12) 1_445 1_445 ? O5 Ca1 C1 25.47(12) 1_445 1_445 ? O1 Ca1 C1 92.37(11) 4_456 1_445 ? O1 Ca1 P2 106.70(9) . 4_456 ? O1W Ca1 P2 166.27(9) . 4_456 ? O2 Ca1 P2 99.57(8) 1_455 4_456 ? O2 Ca1 P2 28.16(9) 4_456 4_456 ? O2W Ca1 P2 83.63(7) . 4_456 ? O4 Ca1 P2 80.98(8) 1_445 4_456 ? O5 Ca1 P2 91.70(8) 1_445 4_456 ? O1 Ca1 P2 28.86(7) 4_456 4_456 ? C1 Ca1 P2 88.99(9) 1_445 4_456 ? O1 Ca1 Ca1 44.18(8) . 4_556 ? O1W Ca1 Ca1 127.28(8) . 4_556 ? O2 Ca1 Ca1 144.55(8) 1_455 4_556 ? O2 Ca1 Ca1 35.24(8) 4_456 4_556 ? O2W Ca1 Ca1 77.25(9) . 4_556 ? O4 Ca1 Ca1 118.78(9) 1_445 4_556 ? O5 Ca1 Ca1 81.74(8) 1_445 4_556 ? O1 Ca1 Ca1 89.68(7) 4_456 4_556 ? C1 Ca1 Ca1 102.90(11) 1_445 4_556 ? P2 Ca1 Ca1 62.59(4) 4_456 4_556 ? O1 Ca1 Ca1 151.20(9) . 4_456 ? O1W Ca1 Ca1 109.86(8) . 4_456 ? O2 Ca1 Ca1 35.61(7) 1_455 4_456 ? O2 Ca1 Ca1 91.66(9) 4_456 4_456 ? O2W Ca1 Ca1 73.08(9) . 4_456 ? O4 Ca1 Ca1 75.04(8) 1_445 4_456 ? O5 Ca1 Ca1 123.76(8) 1_445 4_456 ? O1 Ca1 Ca1 35.70(7) 4_456 4_456 ? C1 Ca1 Ca1 100.10(10) 1_445 4_456 ? P2 Ca1 Ca1 64.40(4) 4_456 4_456 ? Ca1 Ca1 Ca1 121.03(4) 4_556 4_456 ? C6 N1 C5 111.0(3) . . ? C6 N1 C7 111.4(4) . . ? C5 N1 C7 111.4(3) . . ? C6 N1 H1 107.8 . . ? C5 N1 H1 107.5 . . ? C7 N1 H1 107.7 . . ? P2 O1 Ca1 168.4(2) . . ? P2 O1 Ca1 88.61(15) . 4_556 ? Ca1 O1 Ca1 100.11(11) . 4_556 ? P2 O2 Ca1 143.52(18) . 1_655 ? P2 O2 Ca1 103.00(17) . 4_556 ? Ca1 O2 Ca1 109.15(12) 1_655 4_556 ? C1 O4 Ca1 97.0(3) . 1_665 ? C1 O5 Ca1 89.5(3) . 1_665 ? Ca1 O1W H1X 109.3 . . ? Ca1 O1W H1Y 109.7 . . ? H1X O1W H1Y 141.0 . . ? Ca1 O2W H2X 109.5 . . ? Ca1 O2W H2Y 109.4 . . ? H2X O2W H2Y 109.5 . . ? H3X O3W H3Y 109.9 . . ? H4X O4W H4Y 110.7 . . ? O1 P2 O2 110.68(18) . . ? O1 P2 O3 115.68(18) . . ? O2 P2 O3 113.44(18) . . ? O1 P2 C7 105.4(2) . . ? O2 P2 C7 102.2(2) . . ? O3 P2 C7 108.2(2) . . ? O1 P2 Ca1 62.53(13) . 4_556 ? O2 P2 Ca1 48.84(13) . 4_556 ? O3 P2 Ca1 143.71(14) . 4_556 ? C7 P2 Ca1 106.79(16) . 4_556 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 C1 C2 C5 1.7(6) . . . . ? O5 C1 C2 C5 -177.1(4) . . . . ? Ca1 C1 C2 C5 -74.6(15) 1_665 . . . ? O4 C1 C2 C3 125.1(5) . . . . ? O5 C1 C2 C3 -53.7(6) . . . . ? Ca1 C1 C2 C3 48.8(17) 1_665 . . . ? C1 C2 C3 C4 -179.7(4) . . . . ? C5 C2 C3 C4 -55.9(5) . . . . ? C2 C3 C4 C6 56.6(6) . . . . ? C1 C2 C5 N1 -177.9(3) . . . . ? C3 C2 C5 N1 57.0(5) . . . . ? C3 C4 C6 N1 -57.9(5) . . . . ? C4 C6 N1 C5 59.5(5) . . . . ? C4 C6 N1 C7 -175.8(4) . . . . ? C2 C5 N1 C6 -59.2(5) . . . . ? C2 C5 N1 C7 176.1(4) . . . . ? P2 C7 N1 C6 83.8(4) . . . . ? P2 C7 N1 C5 -151.7(3) . . . . ? O1W Ca1 O1 P2 -29.7(10) . . . . ? O2 Ca1 O1 P2 -93.8(10) 1_455 . . . ? O2 Ca1 O1 P2 135.1(10) 4_456 . . . ? O2W Ca1 O1 P2 -138.5(11) . . . . ? O4 Ca1 O1 P2 48.7(11) 1_445 . . . ? O5 Ca1 O1 P2 52.2(10) 1_445 . . . ? O1 Ca1 O1 P2 157.4(10) 4_456 . . . ? C1 Ca1 O1 P2 47.4(11) 1_445 . . . ? P2 Ca1 O1 P2 141.7(10) 4_456 . . . ? Ca1 Ca1 O1 P2 138.3(11) 4_556 . . . ? Ca1 Ca1 O1 P2 -151.3(9) 4_456 . . . ? O1W Ca1 O1 Ca1 -168.09(12) . . . 4_556 ? O2 Ca1 O1 Ca1 127.90(14) 1_455 . . 4_556 ? O2 Ca1 O1 Ca1 -3.27(11) 4_456 . . 4_556 ? O2W Ca1 O1 Ca1 83.13(10) . . . 4_556 ? O4 Ca1 O1 Ca1 -89.67(16) 1_445 . . 4_556 ? O5 Ca1 O1 Ca1 -86.10(11) 1_445 . . 4_556 ? O1 Ca1 O1 Ca1 19.03(11) 4_456 . . 4_556 ? C1 Ca1 O1 Ca1 -90.90(13) 1_445 . . 4_556 ? P2 Ca1 O1 Ca1 3.35(11) 4_456 . . 4_556 ? Ca1 Ca1 O1 Ca1 70.3(2) 4_456 . . 4_556 ? O5 C1 O4 Ca1 14.1(5) . . . 1_665 ? C2 C1 O4 Ca1 -164.7(4) . . . 1_665 ? O4 C1 O5 Ca1 -13.1(5) . . . 1_665 ? C2 C1 O5 Ca1 165.6(4) . . . 1_665 ? Ca1 O1 P2 O2 -130.6(10) . . . . ? Ca1 O1 P2 O2 8.50(16) 4_556 . . . ? Ca1 O1 P2 O3 0.2(11) . . . . ? Ca1 O1 P2 O3 139.29(16) 4_556 . . . ? Ca1 O1 P2 C7 119.7(10) . . . . ? Ca1 O1 P2 C7 -101.23(18) 4_556 . . . ? Ca1 O1 P2 Ca1 -139.1(11) . . . 4_556 ? Ca1 O2 P2 O1 141.4(3) 1_655 . . . ? Ca1 O2 P2 O1 -10.04(19) 4_556 . . . ? Ca1 O2 P2 O3 9.5(4) 1_655 . . . ? Ca1 O2 P2 O3 -141.99(17) 4_556 . . . ? Ca1 O2 P2 C7 -106.8(3) 1_655 . . . ? Ca1 O2 P2 C7 101.8(2) 4_556 . . . ? Ca1 O2 P2 Ca1 151.5(4) 1_655 . . 4_556 ? N1 C7 P2 O1 160.6(3) . . . . ? N1 C7 P2 O2 44.9(3) . . . . ? N1 C7 P2 O3 -75.1(3) . . . . ? N1 C7 P2 Ca1 95.2(3) . . . 4_556 ? 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 H1 O2W 0.91 2.24 3.080(5) 153.9 1_655 N1 H1 O2 0.91 2.36 2.911(5) 119.0 . O1W H1Y O3 0.96 1.84 2.782(4) 167.4 1_455 O2W H2X O5 0.96 1.89 2.837(5) 167.2 4_366 O2W H2Y O4 0.96 1.81 2.722(5) 157.8 4_466 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.392 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.077