#------------------------------------------------------------------------------ #$Date: 2020-06-30 07:22:57 +0300 (Tue, 30 Jun 2020) $ #$Revision: 253552 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/07/7240798.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7240798 loop_ _publ_author_name 'Olyshevets, Iryna' 'Ovchynnikov, Vladimir' 'Kariaka, Nataliia' 'Dyakonenko, Viktoriya' 'Shishkina, Svitlana' 'Sliva, Tatiana' 'Ostrowska, Ma\/lgorzata' 'Jedy\'nczuk, Aleksandra' 'Gumienna-Kontecka, El\.zbieta' 'Amirkhanov, Vladimir' _publ_section_title ; Lanthanide complexes based on a new bis-chelating carbacylamidophosphate (CAPh) scorpionate-like ligand ; _journal_issue 42 _journal_name_full 'RSC Advances' _journal_page_first 24808 _journal_paper_doi 10.1039/D0RA04714G _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C11 H18 N5 Na O8 P2, C3 H8 O' _chemical_formula_sum 'C14 H26 N5 Na O9 P2' _chemical_formula_weight 493.33 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2020-02-16 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-02-16 deposited with the CCDC. 2020-06-22 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 108.507(16) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.740(2) _cell_length_b 17.912(3) _cell_length_c 9.9299(15) _cell_measurement_reflns_used 837 _cell_measurement_temperature 294 _cell_measurement_theta_max 18.8020 _cell_measurement_theta_min 3.3830 _cell_volume 2317.5(7) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 294 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.1827 _diffrn_detector_type Sapphire3 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -23.00 3.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - -25.3583 -77.0000 150.0000 26 #__ type_ start__ end____ width___ exp.time_ 2 omega 0.00 77.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 26.7645 77.0000 120.0000 77 #__ type_ start__ end____ width___ exp.time_ 3 omega -42.00 14.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 26.7645 -57.0000 60.0000 56 #__ type_ start__ end____ width___ exp.time_ 4 omega 23.00 69.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 26.7645 -99.0000 0.0000 46 #__ type_ start__ end____ width___ exp.time_ 5 omega 19.00 96.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 26.7645 57.0000 -150.0000 77 #__ type_ start__ end____ width___ exp.time_ 6 omega -12.00 70.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 26.7645 19.0000 60.0000 82 #__ type_ start__ end____ width___ exp.time_ 7 omega 6.00 89.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 26.7645 57.0000 -60.0000 83 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0366633000 _diffrn_orient_matrix_UB_12 -0.0292764000 _diffrn_orient_matrix_UB_13 0.0156133000 _diffrn_orient_matrix_UB_21 0.0186185000 _diffrn_orient_matrix_UB_22 0.0127180000 _diffrn_orient_matrix_UB_23 -0.0548944000 _diffrn_orient_matrix_UB_31 0.0356096000 _diffrn_orient_matrix_UB_32 0.0234820000 _diffrn_orient_matrix_UB_33 0.0491756000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1295 _diffrn_reflns_av_unetI/netI 0.1453 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 20367 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.499 _diffrn_reflns_theta_min 3.127 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.260 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.34264 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.414 _exptl_crystal_description block _exptl_crystal_F_000 1032 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.363 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.067 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 287 _refine_ls_number_reflns 5320 _refine_ls_number_restraints 18 _refine_ls_restrained_S_all 1.057 _refine_ls_R_factor_all 0.2012 _refine_ls_R_factor_gt 0.0964 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0667P)^2^+1.1471P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1778 _refine_ls_wR_factor_ref 0.2182 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2506 _reflns_number_total 5320 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra04714g2.cif _cod_data_source_block k300a _cod_original_cell_volume 2317.5(6) _cod_database_code 7240798 _shelx_shelxl_version_number 2018/1 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.950 _shelx_estimated_absorpt_t_min 0.881 _reflns_odcompleteness_completeness 89.83 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 32.35 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2. Uiso/Uaniso restraints and constraints O9 \\sim C12 \\sim C13 \\sim C14: within 1.8A with sigma of 0.005 and sigma for terminal atoms of 0.01 3.a Ternary CH refined with riding coordinates: C12(H12) 3.b Aromatic/amide H refined with riding coordinates: N2(H2), N4(H4), N5(H5), C5(H5A), C6(H6), C7(H7) 3.c Idealised Me refined as rotating group: C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C) 3.d Idealised tetrahedral OH refined as rotating group: O9(H9) ; _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.72512(11) 0.50006(9) 0.60896(16) 0.0508(4) Uani 1 1 d . . . . . P2 P 0.43469(11) 0.65310(9) 0.05434(15) 0.0486(4) Uani 1 1 d . . . . . Na1 Na 0.51295(14) 0.57428(11) 0.3924(2) 0.0414(5) Uani 1 1 d . . . . . O1 O 0.7436(4) 0.5686(3) 0.7148(5) 0.0979(17) Uani 1 1 d . . . . . O2 O 0.7853(3) 0.4401(3) 0.7160(5) 0.0972(18) Uani 1 1 d . . . . . O3 O 0.6165(3) 0.4829(2) 0.5455(4) 0.0553(11) Uani 1 1 d . . . . . O4 O 0.6776(2) 0.60153(18) 0.3683(3) 0.0381(8) Uani 1 1 d . . . . . O5 O 0.5004(3) 0.8015(2) -0.0405(4) 0.0579(11) Uani 1 1 d . . . . . O6 O 0.3509(3) 0.7133(3) 0.0379(5) 0.0727(13) Uani 1 1 d . . . . . O7 O 0.4034(5) 0.6279(3) -0.1028(5) 0.112(2) Uani 1 1 d . . . . . O8 O 0.4418(3) 0.5935(2) 0.1559(4) 0.0506(10) Uani 1 1 d . . . . . N1 N 0.7931(3) 0.5176(2) 0.5088(4) 0.0455(11) Uani 1 1 d . . . . . N2 N 0.8267(3) 0.5737(2) 0.3257(4) 0.0431(11) Uani 1 1 d . . . . . H2 H 0.874043 0.540365 0.341695 0.052 Uiso 1 1 calc R . . . . N3 N 0.7478(3) 0.6708(2) 0.1735(4) 0.0400(10) Uani 1 1 d . . . . . N4 N 0.6650(3) 0.7669(2) 0.0246(5) 0.0492(12) Uani 1 1 d . . . . . H4 H 0.675434 0.807511 -0.015015 0.059 Uiso 1 1 calc R . . . . N5 N 0.5463(3) 0.6952(2) 0.0907(4) 0.0436(11) Uani 1 1 d . . . . . H5 H 0.596150 0.677195 0.159099 0.052 Uiso 1 1 calc R . . . . C1 C 0.6943(9) 0.5758(6) 0.8165(9) 0.152(5) Uani 1 1 d . . . . . H1A H 0.622835 0.586110 0.770548 0.227 Uiso 1 1 calc GR . . . . H1B H 0.724703 0.615951 0.879791 0.227 Uiso 1 1 calc GR . . . . H1C H 0.701182 0.530120 0.869417 0.227 Uiso 1 1 calc GR . . . . C2 C 0.7800(8) 0.3662(5) 0.6801(12) 0.152(5) Uani 1 1 d . . . . . H2A H 0.711157 0.354131 0.623063 0.229 Uiso 1 1 calc GR . . . . H2B H 0.798830 0.336400 0.764851 0.229 Uiso 1 1 calc GR . . . . H2C H 0.826158 0.356196 0.627310 0.229 Uiso 1 1 calc GR . . . . C3 C 0.7593(3) 0.5659(3) 0.4029(5) 0.0317(11) Uani 1 1 d . . . . . C4 C 0.8292(4) 0.6275(3) 0.2266(5) 0.0405(12) Uani 1 1 d . . . . . C5 C 0.9162(4) 0.6348(4) 0.1880(7) 0.0634(18) Uani 1 1 d . . . . . H5A H 0.971824 0.602937 0.224723 0.076 Uiso 1 1 calc R . . . . C6 C 0.9192(5) 0.6898(4) 0.0945(7) 0.077(2) Uani 1 1 d . . . . . H6 H 0.978323 0.696978 0.069702 0.092 Uiso 1 1 calc R . . . . C7 C 0.8360(4) 0.7344(4) 0.0372(7) 0.0649(18) Uani 1 1 d . . . . . H7 H 0.836295 0.770997 -0.028989 0.078 Uiso 1 1 calc R . . . . C8 C 0.7514(4) 0.7233(3) 0.0805(6) 0.0453(13) Uani 1 1 d . . . . . C9 C 0.5670(4) 0.7566(3) 0.0215(6) 0.0457(13) Uani 1 1 d . . . . . C10 C 0.3574(6) 0.7658(6) 0.1474(9) 0.116(3) Uani 1 1 d . . . . . H10A H 0.401869 0.806000 0.141050 0.174 Uiso 1 1 calc GR . . . . H10B H 0.384397 0.741736 0.238067 0.174 Uiso 1 1 calc GR . . . . H10C H 0.290224 0.785057 0.137139 0.174 Uiso 1 1 calc GR . . . . C11 C 0.3973(7) 0.5579(4) -0.1542(8) 0.112(3) Uani 1 1 d . . . . . H11A H 0.374598 0.559485 -0.256150 0.169 Uiso 1 1 calc GR . . . . H11B H 0.349313 0.529690 -0.122568 0.169 Uiso 1 1 calc GR . . . . H11C H 0.463640 0.534757 -0.120689 0.169 Uiso 1 1 calc GR . . . . O9 O 1.0059(3) 0.5267(3) 0.6588(5) 0.0755(13) Uani 1 1 d . U . . . H9 H 0.945144 0.521644 0.612428 0.113 Uiso 1 1 calc GR . . . . C12 C 1.0209(6) 0.5970(5) 0.7255(11) 0.115(3) Uani 1 1 d . U . . . H12 H 0.955526 0.622361 0.713757 0.138 Uiso 1 1 calc R . . . . C13 C 1.0867(8) 0.6403(6) 0.6558(12) 0.157(4) Uani 1 1 d . U . . . H13A H 1.152689 0.616858 0.677222 0.235 Uiso 1 1 calc GR . . . . H13B H 1.095156 0.690579 0.691200 0.235 Uiso 1 1 calc GR . . . . H13C H 1.053938 0.640958 0.554829 0.235 Uiso 1 1 calc GR . . . . C14 C 1.0767(9) 0.5826(7) 0.8754(13) 0.188(4) Uani 1 1 d . U . . . H14A H 1.039047 0.547296 0.912336 0.282 Uiso 1 1 calc GR . . . . H14B H 1.084225 0.628378 0.927989 0.282 Uiso 1 1 calc GR . . . . H14C H 1.143233 0.562639 0.884143 0.282 Uiso 1 1 calc GR . . . . 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 0.0469(8) 0.0597(11) 0.0458(9) 0.0122(8) 0.0149(7) -0.0070(8) P2 0.0520(9) 0.0444(9) 0.0459(9) 0.0010(7) 0.0107(7) -0.0115(8) Na1 0.0423(11) 0.0344(11) 0.0498(12) 0.0028(9) 0.0178(9) -0.0043(9) O1 0.112(4) 0.117(5) 0.079(3) -0.037(3) 0.050(3) -0.052(3) O2 0.074(3) 0.117(5) 0.095(4) 0.055(4) 0.018(3) -0.008(3) O3 0.042(2) 0.059(3) 0.064(3) 0.014(2) 0.0147(18) -0.0102(19) O4 0.0323(17) 0.035(2) 0.051(2) 0.0048(17) 0.0192(15) 0.0042(16) O5 0.047(2) 0.041(2) 0.085(3) 0.025(2) 0.019(2) 0.0059(19) O6 0.045(2) 0.068(3) 0.096(3) 0.019(3) 0.009(2) -0.001(2) O7 0.212(6) 0.059(3) 0.054(3) -0.010(2) 0.029(3) -0.057(4) O8 0.051(2) 0.048(2) 0.052(2) 0.0076(19) 0.0150(17) -0.0120(19) N1 0.038(2) 0.047(3) 0.053(3) 0.019(2) 0.015(2) 0.003(2) N2 0.040(2) 0.037(3) 0.059(3) 0.015(2) 0.026(2) 0.015(2) N3 0.036(2) 0.038(3) 0.047(3) 0.007(2) 0.0157(19) 0.003(2) N4 0.043(2) 0.034(3) 0.075(3) 0.024(2) 0.024(2) 0.001(2) N5 0.037(2) 0.035(3) 0.055(3) 0.012(2) 0.010(2) -0.002(2) C1 0.223(11) 0.168(11) 0.106(7) -0.066(7) 0.112(8) -0.077(9) C2 0.137(9) 0.071(7) 0.224(12) 0.008(8) 0.021(8) -0.008(7) C3 0.033(3) 0.026(3) 0.039(3) 0.001(2) 0.016(2) -0.001(2) C4 0.040(3) 0.034(3) 0.050(3) 0.003(3) 0.018(2) 0.002(2) C5 0.042(3) 0.061(4) 0.098(5) 0.029(4) 0.037(3) 0.019(3) C6 0.059(4) 0.072(5) 0.116(6) 0.038(4) 0.052(4) 0.013(4) C7 0.059(4) 0.059(4) 0.089(5) 0.034(4) 0.040(3) 0.008(3) C8 0.044(3) 0.038(3) 0.056(3) 0.009(3) 0.018(3) -0.001(3) C9 0.040(3) 0.040(3) 0.058(4) 0.001(3) 0.017(3) -0.008(3) C10 0.111(6) 0.139(9) 0.112(7) -0.002(6) 0.055(5) 0.044(6) C11 0.170(9) 0.070(6) 0.090(6) -0.018(5) 0.030(6) 0.008(6) O9 0.039(2) 0.068(3) 0.111(4) -0.012(3) 0.012(2) 0.013(2) C12 0.080(5) 0.096(5) 0.157(6) -0.025(5) 0.022(4) -0.004(4) C13 0.140(7) 0.109(7) 0.216(9) -0.005(7) 0.049(6) -0.008(6) C14 0.200(9) 0.167(8) 0.174(8) -0.046(8) 0.027(7) 0.000(7) 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' Na Na 0.0362 0.0249 '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' 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 Na1 92.4(2) . . ? O1 P1 N1 105.0(3) . . ? O2 P1 Na1 153.21(19) . . ? O2 P1 O1 98.3(3) . . ? O2 P1 N1 105.8(3) . . ? O3 P1 Na1 39.79(15) . . ? O3 P1 O1 112.1(3) . . ? O3 P1 O2 113.6(2) . . ? O3 P1 N1 119.6(2) . . ? N1 P1 Na1 94.88(15) . . ? O6 P2 O7 97.9(3) . . ? O6 P2 N5 108.3(2) . . ? O7 P2 N5 107.2(3) . . ? O8 P2 O6 118.0(2) . . ? O8 P2 O7 115.0(2) . . ? O8 P2 N5 109.5(2) . . ? P1 Na1 Na1 62.38(6) . 3_666 ? O3 Na1 P1 23.13(9) . . ? O3 Na1 P1 104.10(11) 3_666 . ? O3 Na1 Na1 42.31(10) 3_666 3_666 ? O3 Na1 Na1 40.69(9) . 3_666 ? O3 Na1 O3 83.00(14) 3_666 . ? O3 Na1 O4 79.16(13) . . ? O3 Na1 O4 162.01(15) 3_666 . ? O3 Na1 O5 102.35(15) 3_666 4_576 ? O4 Na1 P1 58.77(9) . . ? O4 Na1 Na1 119.82(12) . 3_666 ? O5 Na1 P1 109.05(11) 4_576 . ? O5 Na1 Na1 121.13(14) 4_576 3_666 ? O5 Na1 O3 123.73(16) 4_576 . ? O5 Na1 O4 89.54(14) 4_576 . ? O8 Na1 P1 137.51(12) . . ? O8 Na1 Na1 130.85(13) . 3_666 ? O8 Na1 O3 137.90(16) . . ? O8 Na1 O3 103.28(14) . 3_666 ? O8 Na1 O4 88.63(13) . . ? O8 Na1 O5 95.97(15) . 4_576 ? C1 O1 P1 122.8(5) . . ? C2 O2 P1 121.3(6) . . ? P1 O3 Na1 117.1(2) . . ? P1 O3 Na1 138.7(2) . 3_666 ? Na1 O3 Na1 97.00(14) 3_666 . ? C3 O4 Na1 131.8(3) . . ? C9 O5 Na1 130.8(3) . 4_575 ? C10 O6 P2 121.2(4) . . ? C11 O7 P2 128.1(5) . . ? P2 O8 Na1 138.1(2) . . ? C3 N1 P1 119.7(3) . . ? C3 N2 H2 115.3 . . ? C3 N2 C4 129.4(4) . . ? C4 N2 H2 115.3 . . ? C4 N3 C8 118.6(4) . . ? C8 N4 H4 114.5 . . ? C9 N4 H4 114.5 . . ? C9 N4 C8 130.9(5) . . ? P2 N5 H5 117.1 . . ? C9 N5 P2 125.8(4) . . ? C9 N5 H5 117.1 . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 H2A 109.5 . . ? O2 C2 H2B 109.5 . . ? O2 C2 H2C 109.5 . . ? H2A C2 H2B 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? O4 C3 N1 127.8(4) . . ? O4 C3 N2 120.0(4) . . ? N1 C3 N2 112.1(4) . . ? N3 C4 N2 118.8(4) . . ? N3 C4 C5 122.2(5) . . ? C5 C4 N2 118.9(5) . . ? C4 C5 H5A 120.8 . . ? C6 C5 C4 118.4(5) . . ? C6 C5 H5A 120.8 . . ? C5 C6 H6 119.8 . . ? C7 C6 C5 120.4(5) . . ? C7 C6 H6 119.8 . . ? C6 C7 H7 121.1 . . ? C6 C7 C8 117.8(5) . . ? C8 C7 H7 121.1 . . ? N3 C8 N4 117.6(4) . . ? N3 C8 C7 122.7(5) . . ? C7 C8 N4 119.8(5) . . ? O5 C9 N4 120.1(5) . . ? O5 C9 N5 122.3(5) . . ? N4 C9 N5 117.6(5) . . ? O6 C10 H10A 109.5 . . ? O6 C10 H10B 109.5 . . ? O6 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O7 C11 H11A 109.5 . . ? O7 C11 H11B 109.5 . . ? O7 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C12 O9 H9 109.5 . . ? O9 C12 H12 111.5 . . ? O9 C12 C13 105.3(8) . . ? O9 C12 C14 105.7(9) . . ? C13 C12 H12 111.5 . . ? C14 C12 H12 111.5 . . ? C14 C12 C13 111.1(9) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? 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 Na1 3.303(2) . ? P1 O1 1.584(5) . ? P1 O2 1.552(5) . ? P1 O3 1.457(4) . ? P1 N1 1.597(4) . ? P2 O6 1.547(5) . ? P2 O7 1.549(5) . ? P2 O8 1.451(4) . ? P2 N5 1.643(4) . ? Na1 Na1 3.501(4) 3_666 ? Na1 O3 2.374(4) . ? Na1 O3 2.300(4) 3_666 ? Na1 O4 2.399(3) . ? Na1 O5 2.345(4) 4_576 ? Na1 O8 2.265(4) . ? O1 C1 1.389(8) . ? O2 C2 1.367(10) . ? O4 C3 1.241(5) . ? O5 C9 1.227(6) . ? O6 C10 1.418(8) . ? O7 C11 1.346(8) . ? N1 C3 1.327(6) . ? N2 H2 0.8600 . ? N2 C3 1.385(6) . ? N2 C4 1.385(6) . ? N3 C4 1.324(6) . ? N3 C8 1.330(6) . ? N4 H4 0.8600 . ? N4 C8 1.382(6) . ? N4 C9 1.350(6) . ? N5 H5 0.8600 . ? N5 C9 1.373(6) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C4 C5 1.373(7) . ? C5 H5A 0.9300 . ? C5 C6 1.364(8) . ? C6 H6 0.9300 . ? C6 C7 1.362(8) . ? C7 H7 0.9300 . ? C7 C8 1.375(7) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? O9 H9 0.8200 . ? O9 C12 1.408(9) . ? C12 H12 0.9800 . ? C12 C13 1.514(12) . ? C12 C14 1.465(13) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? 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 N2 H2 O9 0.86 2.04 2.885(5) 166.5 3_766 yes N4 H4 O4 0.86 2.00 2.857(5) 170.6 4_575 yes N5 H5 N3 0.86 2.05 2.663(5) 127.9 . yes O9 H9 N1 0.82 2.02 2.834(5) 174.6 . yes