# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Francesca Fabbiani' 'Birger Dittrich' 'Alastair Florence' 'Thomas Gelbrich' 'Mike Hursthouse' 'Werner F. Kuhs' 'Norman Shankland' 'Heidrun Sowa' _publ_contact_author_name 'Francesca Fabbiani' _publ_contact_author_email FFABBIA@GWDG.DE _publ_section_title ; Crystal structures with a challenge: high-pressure crystallisation of ciprofloxacin sodium salts and their recovery to ambient pressure ; # Attachment 'Ciprofloxacin_Fabbiani.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 714344' #Cf anhydrous _chemical_name_common ciprofloxacin _chemical_melting_point ? _chemical_formula_moiety 'C17 H18 F N3 O3' _chemical_formula_structural ? _chemical_formula_sum 'C17 H18 F N3 O3' _chemical_formula_weight 331.34 _chemical_compound_source ; The compound was used as received from Sigma-Aldrich, Fancy Road, Poole, U.K. ; _exptl_crystal_description 'Polycrystalline powder' _exptl_crystal_colour Colourless _exptl_crystal_preparation ; A sample of ciprofloxacin was lightly ground and placed in a rotating 0.7 mm borosilicate glass capillary, mounted on Bruker AXS D8 Advance X-ray powder diffractometer. ; _cell_length_a 7.9606(2) _cell_length_b 8.5798(2) _cell_length_c 10.7739(3) _cell_angle_alpha 87.868(3) _cell_angle_beta 85.153(2) _cell_angle_gamma 88.212(1) _cell_volume 732.43(3) _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_formula_units_Z 2 _cell_measurement_temperature 298 _exptl_crystal_density_diffrn 1.502 _diffrn_ambient_temperature 298 _diffrn_radiation_type 'Cu K\a~1~' _diffrn_radiation_wavelength 1.54056 _diffrn_measurement_device_type ; Bruker-AXS D8 Advance X-ray powder diffractometer ; _refine_ls_hydrogen_treatment refxyz _refine_ls_number_parameters 210 _refine_ls_shift/su_max 0.005 _pd_proc_ls_prof_R_factor 0.037 _pd_proc_ls_prof_wR_factor 0.040 _pd_proc_ls_prof_wR_expected 0.016 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags F1 F Uiso 1.1709(5) 0.0353(4) -0.2543(3) 1.000 0.0168 . DT O1 O Uiso 1.3172(6) 0.4312(4) 0.4202(4) 1.000 0.0168 . DT O2 O Uiso 1.4388(6) 0.2001(5) 0.3903(5) 1.000 0.0168 . DT O3 O Uiso 1.4453(4) 0.1483(4) 0.1285(4) 1.000 0.0168 . DT N1 N Uiso 0.9569(3) 0.3208(2) 0.1835(2) 1.000 0.0168 . DT N2 N Uiso 0.8403(3) 0.1597(3) -0.2309(2) 1.000 0.0168 . DT N3 N Uiso 0.6177(3) 0.2257(3) -0.4274(2) 1.000 0.0168 . DT C1 C Uiso 0.7809(3) 0.3729(2) 0.2023(3) 1.000 0.0168 . DT C2 C Uiso 0.7328(3) 0.5112(3) 0.27919(19) 1.000 0.0168 . DT C3 C Uiso 0.7117(3) 0.5155(3) 0.1407(2) 1.000 0.0168 . DT C4 C Uiso 1.00754(16) 0.25113(13) 0.07328(17) 1.000 0.0168 . DT C5 C Uiso 1.0651(3) 0.3307(3) 0.2720(2) 1.000 0.0168 . DT C6 C Uiso 1.2284(3) 0.2745(3) 0.2598(2) 1.000 0.0168 . DT C7 C Uiso 1.3265(4) 0.3018(3) 0.3689(3) 1.000 0.0168 . DT C8 C Uiso 1.2955(3) 0.2006(3) 0.1476(2) 1.000 0.0168 . DT C9 C Uiso 1.1778(2) 0.18924(17) 0.05275(19) 1.000 0.0168 . DT C10 C Uiso 1.2294(3) 0.1181(3) -0.0602(2) 1.000 0.0168 . DT C11 C Uiso 1.1181(3) 0.1092(3) -0.1489(2) 1.000 0.0168 . DT C12 C Uiso 0.9474(3) 0.1687(3) -0.1341(2) 1.000 0.0168 . DT C13 C Uiso 0.6670(3) 0.2188(3) -0.2015(2) 1.000 0.0168 . DT C14 C Uiso 0.5514(3) 0.1768(3) -0.2994(2) 1.000 0.0168 . DT C15 C Uiso 0.7955(3) 0.1677(3) -0.4558(2) 1.000 0.0168 . DT C16 C Uiso 0.9049(3) 0.2213(3) -0.3570(2) 1.000 0.0168 . DT C17 C Uiso 0.8961(3) 0.2389(3) -0.0209(2) 1.000 0.0168 . DT H11 H Uiso 0.7022(11) 0.2846(11) 0.2135(9) 1.000 0.0201 . DT H21 H Uiso 0.8240(12) 0.5709(10) 0.3099(8) 1.000 0.0201 . DT H22 H Uiso 0.6301(12) 0.5037(11) 0.3373(8) 1.000 0.0201 . DT H31 H Uiso 0.7911(12) 0.5760(11) 0.0833(9) 1.000 0.0201 . DT H32 H Uiso 0.5951(12) 0.5106(13) 0.1143(8) 1.000 0.0201 . DT H51 H Uiso 1.0273(13) 0.3791(12) 0.3470(8) 1.000 0.0201 . DT H101 H Uiso 1.3416(12) 0.0768(11) -0.0747(9) 1.000 0.0201 . DT H131 H Uiso 0.6237(12) 0.1755(11) -0.1188(7) 1.000 0.0201 . DT H132 H Uiso 0.6676(12) 0.3328(11) -0.1964(8) 1.000 0.0201 . DT H141 H Uiso 0.5357(13) 0.0626(11) -0.2958(8) 1.000 0.0201 . DT H142 H Uiso 0.4405(12) 0.2286(11) -0.2807(8) 1.000 0.0201 . DT H151 H Uiso 0.8395(11) 0.2077(10) -0.5388(8) 1.000 0.0201 . DT H152 H Uiso 0.7992(12) 0.0520(12) -0.4572(9) 1.000 0.0201 . DT H161 H Uiso 1.0229(12) 0.1846(11) -0.3771(8) 1.000 0.0201 . DT H162 H Uiso 0.9040(11) 0.3369(12) -0.3581(8) 1.000 0.0201 . DT H171 H Uiso 0.7833(12) 0.2791(11) -0.0072(8) 1.000 0.0201 . DT H311 H Uiso 0.6164(12) 0.3253(10) -0.4355(8) 1.000 0.0201 . DT H312 H Uiso 0.5622(12) 0.1918(11) -0.4867(8) 1.000 0.0201 . DT loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F1 C11 1.351(4) O1 C7 1.256(5) O2 C7 1.259(5) O3 C8 1.264(4) N1 C1 1.457(3) N1 C4 1.374(3) N1 C5 1.345(3) N2 C12 1.407(3) N2 C13 1.468(3) N2 C16 1.495(3) N3 C14 1.485(3) N3 C15 1.496(3) N3 H311 0.856(9) N3 H312 0.870(9) C1 C3 1.483(3) C1 C2 1.494(3) C2 C3 1.515(3) C4 C17 1.412(3) C4 C9 1.443(2) C5 C6 1.370(3) C6 C8 1.441(3) C6 C7 1.495(4) C8 C9 1.451(3) C9 C10 1.406(3) C10 C11 1.363(3) C11 C12 1.435(3) C12 C17 1.404(3) C13 C14 1.517(3) C15 C16 1.524(3) C1 H11 0.996(9) C2 H21 0.988(10) C2 H22 0.989(9) C3 H31 0.991(10) C3 H32 0.996(10) C5 H51 0.945(9) C10 H101 0.953(10) C13 H131 0.991(8) C13 H132 0.982(10) C14 H141 0.991(10) C14 H142 0.985(10) C15 H151 0.986(9) C15 H152 0.993(11) C16 H161 0.990(10) C16 H162 0.991(11) C17 H171 0.954(10) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 N1 C4 117.3(2) C1 N1 C5 122.4(2) C4 N1 C5 120.2(2) C12 N2 C13 115.1(2) C12 N2 C16 117.1(2) C13 N2 C16 109.5(2) C14 N3 C15 111.5(2) C14 N3 H312 114.9(6) C15 N3 H311 107.9(7) C14 N3 H311 110.2(6) H311 N3 H312 106.8(9) C15 N3 H312 105.2(7) N1 C1 C3 123.4(2) N1 C1 C2 120.2(2) C2 C1 C3 61.15(14) C1 C2 C3 59.08(17) C1 C3 C2 59.77(17) C9 C4 C17 119.10(17) N1 C4 C17 121.28(16) N1 C4 C9 119.62(17) N1 C5 C6 123.7(2) C5 C6 C8 120.8(2) C5 C6 C7 114.3(2) C7 C6 C8 124.8(2) O1 C7 O2 122.2(4) O1 C7 C6 120.8(3) O2 C7 C6 115.8(3) O3 C8 C9 120.2(3) C6 C8 C9 115.2(2) O3 C8 C6 124.6(3) C4 C9 C8 120.39(17) C4 C9 C10 119.52(17) C8 C9 C10 120.09(17) C9 C10 C11 119.5(2) C10 C11 C12 123.6(2) F1 C11 C12 118.7(2) F1 C11 C10 117.7(3) N2 C12 C11 120.7(2) C11 C12 C17 116.7(2) N2 C12 C17 122.6(2) N2 C13 C14 111.82(19) N3 C14 C13 112.5(2) N3 C15 C16 109.60(19) N2 C16 C15 110.3(2) C4 C17 C12 121.6(2) N1 C1 H11 112.7(6) C2 C1 H11 115.5(6) C3 C1 H11 114.8(6) C1 C2 H21 118.1(6) C1 C2 H22 117.1(6) C3 C2 H21 118.9(5) C3 C2 H22 117.9(6) H21 C2 H22 114.6(8) C1 C3 H31 116.9(6) C1 C3 H32 116.9(7) C2 C3 H31 119.2(6) C2 C3 H32 117.7(5) H31 C3 H32 115.2(8) N1 C5 H51 118.7(7) C6 C5 H51 117.7(7) C9 C10 H101 120.2(6) C11 C10 H101 120.3(6) N2 C13 H131 109.2(6) N2 C13 H132 109.1(6) C14 C13 H131 109.8(6) C14 C13 H132 109.1(6) H131 C13 H132 107.7(8) N3 C14 H141 109.1(5) N3 C14 H142 108.7(5) C13 C14 H141 109.5(6) C13 C14 H142 108.7(6) H141 C14 H142 108.2(8) N3 C15 H151 110.0(5) N3 C15 H152 109.9(6) C16 C15 H151 109.9(5) C16 C15 H152 109.8(6) H151 C15 H152 107.7(8) N2 C16 H161 110.4(5) N2 C16 H162 109.8(5) C15 C16 H161 109.4(6) C15 C16 H162 109.4(5) H161 C16 H162 107.6(8) C4 C17 H171 119.2(6) C12 C17 H171 119.3(6) _exptl_special_details ; This structure is a laboratory X-ray powder structure determination. ; _refine_special_details ; The diffraction pattern indexed to a triclinic cell in TOPAS (Coelho, 2003) and space group P-1 was assigned from volume considerations. The data set was background subtracted and truncated to 46.8 \% 2\q for Pawley fitting (Pawley, 1981; \c^2^~Pawley~ = 5.6) and the structure solved using the simulated annealing (SA) global optimisation procedure implemented in the DASH computer program (David et al., 2006). The internal coordinate description (including hydrogen atoms) of the molecules were constructed using bond lengths, bond angles and bond torsions for the cirpoflixacin moiety in the crystal structure of ciprofloxacin phosphoric acid monohydrate (CSD refcode: JIRYAL). The structure was solved using data to 46.8\% 2\q, comprising 207 reflections. The SA structure solution involved the optimisation of one molecule of ciprofloxacin, totaling 9 degrees of freedom (3 positional, 3 orientational and 3 torsional). All degrees of freedom were assigned random values at the start of the simulated annealing. The best SA solution had a favourable \c^2^~SA~/\c^2^~Pawley~ ratio of ca. 10, a chemically reasonable packing arrangement and exhibited no significant misfit to the data. The solved structure was subsequently refined against data in the range 5.0 - 69.04 \% 2\q (1.369 \A resolution, 617 reflections) using a restrained Rietveld method (Rietveld, 1969) as implemented in Topas v4.1 (Coelho, 2003), with the R~wp~ falling to 0.0398 during the refinement. All atomic positions (including H-atoms) for the structure were refined, subject to a series of restraints on bond lengths, bond angles and planarity. The restraints were set such that bonds and angles did not deviate more than 0.01 \%A and 1 \% respectively, from their initial values during the refinement. Atoms C1, N1, C5, H51, C6, C7, C8, O3, C9, C10, H101, C11, F1, C12, C17, H171, C4 and N2 were restrained to be planar. A spherical harmonics (4th order) correction of intensities for preferred orientation was applied in the final refinement (J\"arvinen, 1993). The Uiso values for non-hydrogen atoms were constrained to be equal with the Uiso values of hydrogen atoms constrained to be 1.2 times the refined Uiso value for non-hydrogen atoms. As such, no s.u.s are available for the non-hydrogen and hydrogen Usio values. The observed and calculated diffraction patterns for the refined crystal structure are shown in Fig. x. The atomic co-ordinates and s.u.s for all atoms are taken from the software. ; #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 714345' #Cf hemi Na salt crystallised at 0.25 GPa _cell_length_a 9.452(3) _cell_length_b 9.591(4) _cell_length_c 11.233(6) _cell_angle_alpha 85.67(2) _cell_angle_beta 99.62(2) _cell_angle_gamma 93.74(2) _cell_volume 999.7(8) _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 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Na 0.0362 0.0249 4.7626 3.2850 3.1736 8.8422 1.2674 0.3136 1.1128 129.4240 0.6760 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 _chemical_formula_sum 'C17 H27.50 F1 N3 Na0.50 O8' _chemical_formula_moiety 'C17 H17.50 F1 N3 O3, Na0.50, 5(H2O)' _chemical_compound_source ; high-pressure crystallisation at 0.25 GPa ; _chemical_formula_weight 432.41 _cell_measurement_reflns_used 601 _cell_measurement_theta_min 2 _cell_measurement_theta_max 17 _cell_measurement_temperature 293 _exptl_crystal_description colourless _exptl_crystal_colour block _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_max 0.30 _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 458 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'based on symmetry-related measuraments' # SHADE (Parsons, 2004) # SADABS (Siemens, 1996) # The following data are from Sadabs: _exptl_absorpt_correction_T_min 0.54 _exptl_absorpt_correction_T_max 0.99 # Sheldrick geometric approximatio 0.99 0.99 _diffrn_measurement_device 'Bruker Apex2' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'Starting from fract. coordinates of 4' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003), PLATON, XCIF, ENCIFER' _computing_molecular_graphics MERCURY _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 293 _diffrn_reflns_number 5936 _reflns_number_total 513 _diffrn_reflns_av_R_equivalents 0.070 # Number of reflections with Friedels Law is 513 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1216 _diffrn_reflns_reduction_process ; Merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; _diffrn_reflns_theta_min 2.189 _diffrn_reflns_theta_max 17.246 _diffrn_measured_fraction_theta_max 0.423 _diffrn_reflns_theta_full 13.625 _diffrn_measured_fraction_theta_full 0.468 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 7 _reflns_limit_h_min -7 _reflns_limit_h_max 7 _reflns_limit_k_min -5 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 7 _atom_sites_solution_primary ; starting coordinates for cipro moiety taken from the structure of 4 ; _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.25 _refine_diff_density_max 0.32 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 498 _refine_ls_number_restraints 66 _refine_ls_number_parameters 121 _oxford_refine_ls_R_factor_ref 0.1299 _refine_ls_wR_factor_ref 0.2770 _refine_ls_goodness_of_fit_ref 0.9753 _refine_ls_shift/su_max 0.000049 # The values computed from all data _oxford_reflns_number_all 498 _refine_ls_R_factor_all 0.1299 _refine_ls_wR_factor_all 0.2770 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 356 _refine_ls_R_factor_gt 0.1031 _refine_ls_wR_factor_gt 0.2553 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.17P)^2^ + 8.57P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_special_details ; The Following ALERTS were generated by PLATON checkcif<<< 022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.42 023_ALERT_3_A Resolution (too) Low [sin(th)/Lambda < 0.6]..... 17.25 Deg. 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 13.63 Deg. 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.47 088_ALERT_3_A Poor Data / Parameter Ratio .................... 4.12 340_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ... 27 061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.56 084_ALERT_2_C High R2 Value .................................. 0.28 These alerts are not uncommon for high-pressure data and indicate that the structure quality is not high. The geometry of the diamond-anvil cell severely restricts the amount of recirpocal space that can be accessed, resulting in a poor completeness. This is more evident for lower-symmetry crystal systems (triclinic in this case). The data is not only incomplete but also weak, as testified by diffraction to a maximum d of 1.2 A. The use of restraints, 66 in total, increases the data to parameter ratio to 4.7. Related to the use of restraints, we note tat the calculation of bond precision by the Checkcif procedure does not take into account the off diagonal terms of the variance-covariance matrix. 201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) ....... 25 210_ALERT_3_B No Anisotropic ADP's Found in CIF .............. ? 202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent ......... 4 All non-H-atoms were refined with isotropic thermal parameters 242_ALERT_2_A Check Low Ueq as Compared to Neighbors for Na1 Ueq for Na1 is within expected range. Ueq for O100 (water) is larger than expected and this atom is probably disordered but given the paucity of the data the model was kept as given. 306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O101 306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O102 306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O103 306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O104 430_ALERT_2_B Short Inter D...A Contact O1 .. O102 .. 2.74 Ang. 430_ALERT_2_B Short Inter D...A Contact O1 .. O101 .. 2.76 Ang. 430_ALERT_2_B Short Inter D...A Contact O2 .. O104 .. 2.73 Ang. 430_ALERT_2_B Short Inter D...A Contact O100 .. O103 .. 2.68 Ang. 430_ALERT_2_B Short Inter D...A Contact O103 .. O104 .. 2.84 Ang. 430_ALERT_2_C Short Inter D...A Contact O100 .. O102 .. 2.89 Ang. 430_ALERT_2_C Short Inter D...A Contact O103 .. O103 .. 2.85 Ang. No information could be inferred from the data about the position of water H-atoms and given the intricated network of H-bonding pattern, no water H-atoms were placed geometrically. 041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? 042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? 043_ALERT_1_C Check Reported Molecular Weight ................ 432.41 044_ALERT_1_C Calculated and Reported Dx Differ .............. ? 045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio 068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? The formulae given and derived properties are correct. Although no water H-atoms are present in the model, these were included for the calculation of formulae, molecular weight, density, mu and F000. 155_ALERT_4_C The Triclinic Unitcell is NOT Reduced .......... ? The cell was chose to facilitate comparision with the known structure of Cf hexahydrate, CSD ref. code COVPIN and the other structures presented in this work. 301_ALERT_3_C Main Residue Disorder ......................... 2.00 Perc. Na1 is disorderd over an inversion centre. 369_ALERT_2_C Long C(sp2)-C(sp2) Bond C6 - C7 ... 1.54 Ang. 731_ALERT_1_C Bond Calc 1.50(3), Rep 1.502(13) ...... 2.31 su-Ra C3 -C2 1.555 1.555 731_ALERT_1_C Bond Calc 1.39(3), Rep 1.388(14) ...... 2.14 su-Ra C4 -C9 1.555 1.555 731_ALERT_1_C Bond Calc 1.41(3), Rep 1.406(14) ...... 2.14 su-Ra C4 -C17 1.555 1.555 731_ALERT_1_C Bond Calc 1.37(3), Rep 1.369(13) ...... 2.31 su-Ra C5 -N1 1.555 1.555 731_ALERT_1_C Bond Calc 1.54(3), Rep 1.533(13) ...... 2.31 su-Ra C6 -C7 1.555 1.555 731_ALERT_1_C Bond Calc 1.24(3), Rep 1.246(13) ...... 2.31 su-Ra C7 -O2 1.555 1.555 731_ALERT_1_C Bond Calc 1.45(3), Rep 1.448(13) ...... 2.31 su-Ra C8 -C9 1.555 1.555 731_ALERT_1_C Bond Calc 1.35(3), Rep 1.351(13) ...... 2.31 su-Ra C10 -C11 1.555 1.555 731_ALERT_1_C Bond Calc 1.41(3), Rep 1.411(14) ...... 2.14 su-Ra C11 -C12 1.555 1.555 731_ALERT_1_C Bond Calc 1.41(3), Rep 1.408(12) ...... 2.50 su-Ra C12 -N2 1.555 1.555 731_ALERT_1_C Bond Calc 1.51(3), Rep 1.503(14) ...... 2.14 su-Ra C13 -C14 1.555 1.555 731_ALERT_1_C Bond Calc 1.51(3), Rep 1.506(14) ...... 2.14 su-Ra C15 -C16 1.555 1.555 732_ALERT_1_C Angle Calc 118.1(17), Rep 118.1(7) ...... 2.43 su-Ra C9 -C4 -N1 1.555 1.555 1.555 732_ALERT_1_C Angle Calc 120.7(17), Rep 120.8(8) ...... 2.13 su-Ra C17 -C4 -N1 1.555 1.555 1.555 732_ALERT_1_C Angle Calc 118.9(18), Rep 118.9(7) ...... 2.57 su-Ra C5 -C6 -C8 1.555 1.555 1.555 732_ALERT_1_C Angle Calc 126(2), Rep 125.5(9) ...... 2.22 su-Ra O1 -C7 -O2 1.555 1.555 1.555 732_ALERT_1_C Angle Calc 123.3(19), Rep 123.2(8) ...... 2.38 su-Ra C6 -C8 -O3 1.555 1.555 1.555 732_ALERT_1_C Angle Calc 118.4(17), Rep 118.5(8) ...... 2.13 su-Ra C8 -C9 -C10 1.555 1.555 1.555 732_ALERT_1_C Angle Calc 118.5(18), Rep 118.3(8) ...... 2.25 su-Ra C4 -C9 -C10 1.555 1.555 1.555 732_ALERT_1_C Angle Calc 119.4(17), Rep 119.7(8) ...... 2.13 su-Ra C9 -C10 -C11 1.555 1.555 1.555 732_ALERT_1_C Angle Calc 118.4(17), Rep 118.3(8) ...... 2.13 su-Ra C12 -C11 -F1 1.555 1.555 1.555 732_ALERT_1_C Angle Calc 116.4(17), Rep 116.3(8) ...... 2.13 su-Ra C11 -C12 -C17 1.555 1.555 1.555 779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 29.20 Deg. NA1 -O2 -NA1 2.567 1.555 1.555 779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 29.30 Deg. NA1 -O3 -NA1 2.567 1.555 1.555 860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 66 These alerts stem from the fact that PLATON calculates e.s.d.s using only the variances whereas CRYSTALS uses the full variance/covariance matrix. Soft restraints were used on all bond lengths and angles of the Cf moiety. 154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 2000 Deg. 790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 O 790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 4 O 790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 5 O Noted, no action taken. The centre of gravity of the main Cf moiety is within the unit cell. Water O-atoms were transformed to give a clear picture of the coordination environment of the Cf moiety. 199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K 200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K Data were collected at room temperature ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Sheldrick, G. M. (2008). Acta Cryst A64, 112-122. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens C1 C 0.2308(13) 0.3570(17) 0.4368(18) 0.044(6) 1.0000 Uiso D . . . . . . C2 C 0.3893(14) 0.347(2) 0.458(3) 0.060(7) 1.0000 Uiso D . . . . . . C3 C 0.2906(16) 0.224(2) 0.420(3) 0.051(6) 1.0000 Uiso D . . . . . . C4 C 0.0216(14) 0.296(2) 0.5406(19) 0.039(6) 1.0000 Uiso D . . . . . . C5 C 0.2125(13) 0.449(2) 0.632(2) 0.027(5) 1.0000 Uiso D . . . . . . C6 C 0.1477(13) 0.466(2) 0.7305(19) 0.034(6) 1.0000 Uiso D . . . . . . C7 C 0.2345(13) 0.547(2) 0.834(2) 0.041(6) 1.0000 Uiso D . . . . . . C8 C 0.0125(14) 0.393(2) 0.7391(19) 0.035(5) 1.0000 Uiso D . . . . . . C9 C -0.0496(14) 0.313(2) 0.6365(19) 0.040(6) 1.0000 Uiso D . . . . . . C10 C -0.1868(14) 0.247(2) 0.636(2) 0.032(5) 1.0000 Uiso D . . . . . . C11 C -0.2457(14) 0.170(2) 0.5424(19) 0.033(6) 1.0000 Uiso D . . . . . . C12 C -0.1779(13) 0.152(2) 0.4422(18) 0.035(6) 1.0000 Uiso D . . . . . . C13 C -0.1540(14) 0.028(2) 0.265(2) 0.042(6) 1.0000 Uiso D . . . . . . C14 C -0.2261(15) -0.089(2) 0.191(3) 0.053(7) 1.0000 Uiso D . . . . . . C15 C -0.4596(14) -0.022(2) 0.222(2) 0.051(6) 1.0000 Uiso D . . . . . . C16 C -0.3891(13) 0.097(2) 0.295(2) 0.039(6) 1.0000 Uiso D . . . . . . C17 C -0.0432(14) 0.218(2) 0.443(2) 0.030(5) 1.0000 Uiso D . . . . . . O1 O 0.3678(11) 0.5644(17) 0.831(2) 0.051(4) 1.0000 Uiso D . . . . . . O2 O 0.1688(12) 0.5997(19) 0.905(2) 0.065(5) 1.0000 Uiso D . . . . . . O3 O -0.0562(12) 0.4061(17) 0.822(2) 0.057(4) 1.0000 Uiso D . . . . . . N1 N 0.1552(11) 0.3674(17) 0.5391(17) 0.039(5) 1.0000 Uiso D . . . . . . N2 N -0.2433(10) 0.0609(15) 0.3537(17) 0.029(4) 1.0000 Uiso D . . . . . . N3 N -0.3697(13) -0.0502(18) 0.130(2) 0.046(5) 1.0000 Uiso D . . . . . . F1 F -0.3738(9) 0.0978(14) 0.5500(17) 0.044(3) 1.0000 Uiso D . . . . . . Na1 Na 0.0276(15) 0.451(2) 1.026(3) 0.061(6) 0.5000 Uiso . . . . . . . O100 O 0.152(3) 0.269(4) 1.125(5) 0.223(13) 1.0000 Uiso . . . . . . . O101 O 0.4297(19) 0.607(3) 1.219(4) 0.149(8) 1.0000 Uiso . . . . . . . O102 O 0.4125(14) 0.303(2) 1.021(3) 0.097(6) 1.0000 Uiso . . . . . . . O103 O 0.1059(19) -0.008(3) 1.106(4) 0.150(9) 1.0000 Uiso . . . . . . . O104 O -0.3014(13) 0.185(2) -0.034(3) 0.076(5) 1.0000 Uiso . . . . . . . H11 H 0.1925 0.4086 0.3644 0.0526 1.0000 Uiso . . . . . . . H21 H 0.4417 0.3479 0.5384 0.0718 1.0000 Uiso . . . . . . . H22 H 0.4456 0.3945 0.4037 0.0718 1.0000 Uiso . . . . . . . H31 H 0.2807 0.1458 0.4762 0.0602 1.0000 Uiso . . . . . . . H32 H 0.2846 0.1925 0.3415 0.0602 1.0000 Uiso . . . . . . . H51 H 0.3035 0.4958 0.6290 0.0326 1.0000 Uiso . . . . . . . H101 H -0.2380 0.2575 0.7001 0.0380 1.0000 Uiso . . . . . . . H171 H 0.0061 0.2106 0.3770 0.0352 1.0000 Uiso . . . . . . . H131 H -0.0630 0.0002 0.3062 0.0498 1.0000 Uiso . . . . . . . H132 H -0.1410 0.1086 0.2125 0.0498 1.0000 Uiso . . . . . . . H141 H -0.2356 -0.1710 0.2433 0.0628 1.0000 Uiso . . . . . . . H142 H -0.1694 -0.1075 0.1325 0.0628 1.0000 Uiso . . . . . . . H151 H -0.5523 0.0026 0.1828 0.0611 1.0000 Uiso . . . . . . . H152 H -0.4680 -0.1033 0.2748 0.0611 1.0000 Uiso . . . . . . . H161 H -0.4449 0.1137 0.3548 0.0471 1.0000 Uiso . . . . . . . H162 H -0.3830 0.1792 0.2425 0.0471 1.0000 Uiso . . . . . . . H311 H -0.4111 -0.1194 0.0871 0.0548 1.0000 Uiso . . . . . . . H312 H -0.3612 0.0254 0.0816 0.0548 0.5000 Uiso . . . . . . . _refine_ls_extinction_method None _oxford_refine_ls_scale 4.5(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.485(13) yes C1 . C3 . 1.466(11) yes C1 . N1 . 1.463(14) yes C1 . H11 . 0.949 no C2 . C3 . 1.502(13) yes C2 . H21 . 0.953 no C2 . H22 . 0.948 no C3 . H31 . 0.950 no C3 . H32 . 0.949 no C4 . C9 . 1.388(14) yes C4 . C17 . 1.406(14) yes C4 . N1 . 1.398(12) yes C5 . C6 . 1.373(15) yes C5 . N1 . 1.369(13) yes C5 . H51 . 0.950 no C6 . C7 . 1.533(13) yes C6 . C8 . 1.431(13) yes C7 . O1 . 1.265(11) yes C7 . O2 . 1.246(13) yes C8 . C9 . 1.448(13) yes C8 . O3 . 1.239(15) yes C9 . C10 . 1.404(13) yes C10 . C11 . 1.351(13) yes C10 . H101 . 0.950 no C11 . C12 . 1.411(14) yes C11 . F1 . 1.367(12) yes C12 . C17 . 1.385(13) yes C12 . N2 . 1.408(12) yes C13 . C14 . 1.503(14) yes C13 . N2 . 1.475(14) yes C13 . H131 . 0.951 no C13 . H132 . 0.949 no C14 . N3 . 1.474(16) yes C14 . H141 . 0.951 no C14 . H142 . 0.950 no C15 . C16 . 1.506(14) yes C15 . N3 . 1.498(15) yes C15 . H151 . 0.948 no C15 . H152 . 0.952 no C16 . N2 . 1.478(14) yes C16 . H161 . 0.951 no C16 . H162 . 0.948 no C17 . H171 . 0.950 no O2 . Na1 2_567 2.14(3) yes O2 . Na1 . 2.39(4) yes O3 . Na1 2_567 2.24(3) yes O3 . Na1 . 2.36(4) yes N3 . H311 . 0.881 no N3 . H312 . 0.879 no Na1 . O100 . 2.29(6) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C3 . C1 . C2 . 61.2(6) yes C3 . C1 . N1 . 119.3(11) yes C2 . C1 . N1 . 119.9(11) yes C3 . C1 . H11 . 115.4 no C2 . C1 . H11 . 115.3 no N1 . C1 . H11 . 115.2 no C1 . C3 . C2 . 60.1(6) yes C1 . C3 . H31 . 120.0 no C2 . C3 . H31 . 120.0 no C1 . C3 . H32 . 119.9 no C2 . C3 . H32 . 119.9 no H31 . C3 . H32 . 109.6 no C3 . C2 . C1 . 58.8(6) yes C3 . C2 . H21 . 120.1 no C1 . C2 . H21 . 120.1 no C3 . C2 . H22 . 120.4 no C1 . C2 . H22 . 120.3 no H21 . C2 . H22 . 109.4 no C9 . C4 . C17 . 121.0(8) yes C9 . C4 . N1 . 118.1(7) yes C17 . C4 . N1 . 120.8(8) yes C6 . C5 . N1 . 124.3(8) yes C6 . C5 . H51 . 117.8 no N1 . C5 . H51 . 117.8 no C5 . C6 . C7 . 117.5(8) yes C5 . C6 . C8 . 118.9(7) yes C7 . C6 . C8 . 123.1(9) yes C6 . C7 . O1 . 115.4(9) yes C6 . C7 . O2 . 118.7(8) yes O1 . C7 . O2 . 125.5(9) yes C6 . C8 . C9 . 115.7(8) yes C6 . C8 . O3 . 123.2(8) yes C9 . C8 . O3 . 120.7(8) yes C8 . C9 . C4 . 123.1(7) yes C8 . C9 . C10 . 118.5(8) yes C4 . C9 . C10 . 118.3(8) yes C9 . C10 . C11 . 119.7(8) yes C9 . C10 . H101 . 120.1 no C11 . C10 . H101 . 120.2 no C10 . C11 . C12 . 123.8(8) yes C10 . C11 . F1 . 117.7(9) yes C12 . C11 . F1 . 118.3(8) yes C11 . C12 . C17 . 116.3(8) yes C11 . C12 . N2 . 119.6(8) yes C17 . C12 . N2 . 123.9(8) yes C14 . C13 . N2 . 110.0(10) yes C14 . C13 . H131 . 109.2 no N2 . C13 . H131 . 109.3 no C14 . C13 . H132 . 109.3 no N2 . C13 . H132 . 109.5 no H131 . C13 . H132 . 109.5 no C13 . C14 . N3 . 110.2(14) yes C13 . C14 . H141 . 109.4 no N3 . C14 . H141 . 109.3 no C13 . C14 . H142 . 109.4 no N3 . C14 . H142 . 109.3 no H141 . C14 . H142 . 109.3 no C16 . C15 . N3 . 109.4(10) yes C16 . C15 . H151 . 109.7 no N3 . C15 . H151 . 109.5 no C16 . C15 . H152 . 109.5 no N3 . C15 . H152 . 109.3 no H151 . C15 . H152 . 109.4 no C15 . C16 . N2 . 109.6(10) yes C15 . C16 . H161 . 109.3 no N2 . C16 . H161 . 109.4 no C15 . C16 . H162 . 109.4 no N2 . C16 . H162 . 109.5 no H161 . C16 . H162 . 109.6 no C4 . C17 . C12 . 120.9(9) yes C4 . C17 . H171 . 119.5 no C12 . C17 . H171 . 119.6 no Na1 2_567 O2 . C7 . 135.3(10) yes Na1 2_567 O2 . Na1 . 29.2(13) yes C7 . O2 . Na1 . 119.4(15) yes Na1 2_567 O3 . C8 . 133.3(11) yes Na1 2_567 O3 . Na1 . 29.3(13) yes C8 . O3 . Na1 . 129.7(10) yes C1 . N1 . C4 . 119.8(8) yes C1 . N1 . C5 . 120.7(8) yes C4 . N1 . C5 . 119.6(8) yes C16 . N2 . C13 . 111.7(11) yes C16 . N2 . C12 . 114.5(9) yes C13 . N2 . C12 . 115.9(8) yes C15 . N3 . C14 . 109.4(11) yes C15 . N3 . H311 . 109.5 no C14 . N3 . H311 . 109.5 no C15 . N3 . H312 . 109.5 no C14 . N3 . H312 . 109.5 no H311 . N3 . H312 . 109.5 no O3 . Na1 . O3 2_567 150.7(13) yes O3 . Na1 . O2 . 72.6(12) yes O3 2_567 Na1 . O2 . 94.7(9) yes O3 . Na1 . O2 2_567 98.3(10) yes O3 2_567 Na1 . O2 2_567 79.8(10) yes O2 . Na1 . O2 2_567 150.8(13) yes O3 . Na1 . O100 . 110.9(12) yes O3 2_567 Na1 . O100 . 98.4(18) yes O2 . Na1 . O100 . 112.3(11) yes O2 2_567 Na1 . O100 . 96.9(18) yes #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 714346' #Cf hemi Na recovered to ambient pressure _cell_length_a 9.391(8) _cell_length_b 9.570(8) _cell_length_c 11.095(9) _cell_angle_alpha 85.247(14) _cell_angle_beta 99.498(13) _cell_angle_gamma 93.272(14) _cell_volume 979.2(14) _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 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Na 0.0362 0.0249 4.7626 3.2850 3.1736 8.8422 1.2674 0.3136 1.1128 129.4240 0.6760 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 _chemical_formula_sum 'C17 H27.50 F1 N3 Na0.50 O8' _chemical_formula_moiety 'C17 H17.50 F1 N3 O3, Na0.50, 5(H2O)' _chemical_compound_source ; recovery of 2 to ambient pressure ; _chemical_formula_weight 432.41 _cell_measurement_reflns_used 1144 _cell_measurement_theta_min 2 _cell_measurement_theta_max 20 _cell_measurement_temperature 100 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.04 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_max 0.28 _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 458 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'based on symmetry-related measuraments' # SADABS (Siemens, 1996) # The following data are from Sadabs: _exptl_absorpt_correction_T_min 0.72 _exptl_absorpt_correction_T_max 0.99 # Sheldrick geometric approximatio 0.99 0.99 _diffrn_measurement_device 'Bruker Apex2' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'Starting from fract. coordinates of 2' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003), PLATON, XCIF, ENCIFER' _computing_molecular_graphics MERCURY _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 100 _diffrn_reflns_number 6358 _reflns_number_total 1773 _diffrn_reflns_av_R_equivalents 0.103 # Number of reflections with Friedels Law is 1773 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1780 _diffrn_reflns_theta_min 1.866 _diffrn_reflns_theta_max 19.816 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 19.420 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min -8 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 10 _oxford_diffrn_Wilson_B_factor 1.56 _oxford_diffrn_Wilson_scale 5.37 _atom_sites_solution_primary ; starting coordinates for cipro moiety taken from the structure of 4 ; # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.54 _refine_diff_density_max 0.91 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 1772 _refine_ls_number_restraints 331 _refine_ls_number_parameters 270 _oxford_refine_ls_R_factor_ref 0.1286 _refine_ls_wR_factor_ref 0.2300 _refine_ls_goodness_of_fit_ref 0.8956 _refine_ls_shift/su_max 0.000103 # The values computed from all data _oxford_reflns_number_all 1772 _refine_ls_R_factor_all 0.1286 _refine_ls_wR_factor_all 0.2300 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1061 _refine_ls_R_factor_gt 0.0790 _refine_ls_wR_factor_gt 0.1971 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.12P)^2^ + 3.51P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_special_details ; The Following ALERTS were generated by PLATON checkcif<<< 023_ALERT_3_A Resolution (too) Low [sin(th)/Lambda < 0.6]..... 19.82 Deg. 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 19.42 Deg. 911_ALERT_3_B # Missing FCF Refl Between THmin & STh/L= 15 020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10 340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 10 250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.87 The data were cut to 1.05 A for integration as no significan scattering was observed for this small crystal at higher resolution. The dataset is complete to 1.05 A as shown below: #=============================================================================== Resolution & Completeness Statistics (Cumulative) #=============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------- 19.82 0.477 0.992 1788 1773 15 #------------------------------------------------------------------------------- These alerts also indicate that the structure quality is not ideal. However, this is the best structure we could obtain from the data collected on this small, weakly diffracting crystal recovered at ambient pressure. Data were collected at low temperature, with high counting time and with a laboratory X-ray source. The low crystal quality was also reflected in the broad and at times split reflection profiles. Related to the use of restraints, see below, we note tat the calculation of bond precision by the Checkcif procedure does not take into account the off diagonal terms of the variance-covariance matrix. 088_ALERT_3_B Poor Data / Parameter Ratio .................... 6.56 The use of restraints (bond distances and angles as well as thermal vibration and similarity for refinement of ADPs), a total of 332, increases the number of observations to 2104 and gives a data to parameter ratio of 7.8. 097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.91 e/A**3 The largest peak is in the vicinity of the disorderd O-atoms 202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent ......... 1 The disordered O-atoms were refined with isotropic thermal parameters 306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O101 306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O102 306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O103 306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O104 430_ALERT_2_A Short Inter D...A Contact O101 .. O1001 .. 2.50 Ang. 430_ALERT_2_A Short Inter D...A Contact O102 .. O1001 .. 2.46 Ang. 430_ALERT_2_B Short Inter D...A Contact O1 .. O102 .. 2.71 Ang. 430_ALERT_2_B Short Inter D...A Contact O1 .. O101 .. 2.76 Ang. 430_ALERT_2_B Short Inter D...A Contact O1000 .. O103 .. 2.67 Ang. 430_ALERT_2_B Short Inter D...A Contact O1000 .. O102 .. 2.78 Ang. 430_ALERT_2_B Short Inter D...A Contact O2 .. O1001 .. 2.70 Ang. 430_ALERT_2_B Short Inter D...A Contact O2 .. O104 .. 2.72 Ang. 430_ALERT_2_B Short Inter D...A Contact O3 .. O1001 .. 2.56 Ang. 430_ALERT_2_B Short Inter D...A Contact O101 .. O104 .. 2.83 Ang. 430_ALERT_2_B Short Inter D...A Contact O103 .. O103 .. 2.74 Ang. 430_ALERT_2_B Short Inter D...A Contact O103 .. O104 .. 2.78 Ang. No information could be inferred from the data about the position of water H-atoms and given the intricated network of H-bonding pattern as well as the presence of disorder, no water H-atoms were placed geometrically. 061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.75 Sadabs corrects for all systematic errors that lead to disparities in the intensities of equivalent data. It is possible that the larger than expected range of transmission is accounted for by crystal decay or absorption by the mounting fibre. 041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? 042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? 045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio The formulae given and derived properties are correct. Although no water H-atoms are present in the model, these were included for the calculation of formulae, molecular weight, density, mu and F000. 155_ALERT_4_C The Triclinic Unitcell is NOT Reduced .......... ? The cell was chose to facilitate comparision with the known structure of Cf hexahydrate, CSD ref. code COVPIN and the other structures presented in this work. 302_ALERT_4_C Anion/Solvent Disorder ......................... 21.00 Perc. 311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ..... >O1000 311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ..... Apex2, Version 2 User Manual, M86-E01078, Madison, WI. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens C1 C 0.2323(7) 0.3557(7) 0.4339(7) 0.0350 1.0000 Uani D U . . . . . C2 C 0.3936(7) 0.3431(8) 0.4579(8) 0.0427 1.0000 Uani D U . . . . . C3 C 0.2945(8) 0.2203(7) 0.4216(8) 0.0371 1.0000 Uani D U . . . . . C4 C 0.0211(7) 0.2988(7) 0.5381(6) 0.0265 1.0000 Uani D U . . . . . C5 C 0.2145(7) 0.4472(8) 0.6305(7) 0.0361 1.0000 Uani D U . . . . . C6 C 0.1497(7) 0.4667(7) 0.7283(6) 0.0330 1.0000 Uani D U . . . . . C7 C 0.2346(8) 0.5538(8) 0.8245(7) 0.0464 1.0000 Uani D U . . . . . C8 C 0.0108(7) 0.3992(8) 0.7374(7) 0.0375 1.0000 Uani D U . . . . . C9 C -0.0513(7) 0.3151(7) 0.6360(6) 0.0317 1.0000 Uani D U . . . . . C10 C -0.1855(7) 0.2464(8) 0.6373(7) 0.0321 1.0000 Uani D U . . . . . C11 C -0.2452(7) 0.1672(7) 0.5445(6) 0.0300 1.0000 Uani D U . . . . . C12 C -0.1754(6) 0.1490(7) 0.4431(6) 0.0276 1.0000 Uani D U . . . . . C13 C -0.1502(7) 0.0248(8) 0.2646(7) 0.0314 1.0000 Uani D U . . . . . C14 C -0.2235(8) -0.0919(8) 0.1921(7) 0.0362 1.0000 Uani D U . . . . . C15 C -0.4578(7) -0.0180(8) 0.2160(7) 0.0384 1.0000 Uani D U . . . . . C16 C -0.3856(7) 0.0993(8) 0.2900(7) 0.0318 1.0000 Uani D U . . . . . C17 C -0.0418(7) 0.2178(7) 0.4426(6) 0.0271 1.0000 Uani D U . . . . . O1 O 0.3697(6) 0.5655(6) 0.8300(6) 0.0613 1.0000 Uani D U . . . . . O2 O 0.1653(6) 0.6112(7) 0.8933(5) 0.0631 1.0000 Uani D U . . . . . O3 O -0.0583(6) 0.4079(6) 0.8255(5) 0.0572 1.0000 Uani D U . . . . . N1 N 0.1569(6) 0.3677(6) 0.5373(5) 0.0319 1.0000 Uani D U . . . . . N2 N -0.2409(5) 0.0609(6) 0.3535(5) 0.0290 1.0000 Uani D U . . . . . N3 N -0.3667(6) -0.0510(7) 0.1250(5) 0.0381 1.0000 Uani D U . . . . . F1 F -0.3733(4) 0.0959(4) 0.5514(4) 0.0398 1.0000 Uani D U . . . . . Na1 Na 0.0263(7) 0.4396(7) 1.0329(6) 0.0532 0.5000 Uani . U . . . . . O1000 O 0.1532(11) 0.2679(11) 1.1163(10) 0.109(3) 0.8000 Uiso . . . 1 1 . . O1001 O 0.249(3) 0.452(3) 1.103(3) 0.065(9) 0.2000 Uiso . . . 1 2 . . O101 O 0.4310(11) 0.6159(11) 1.2161(8) 0.1400 1.0000 Uani . . . 2 1 . . O102 O 0.4125(8) 0.3021(8) 1.0249(7) 0.0939 1.0000 Uani . . . . . . . O103 O 0.1049(8) -0.0086(10) 1.1015(8) 0.1107 1.0000 Uani . . . . . . . O104 O -0.2985(6) 0.1854(6) -0.0353(5) 0.0541 1.0000 Uani . . . . . . . H11 H 0.1941 0.4064 0.3594 0.0444 1.0000 Uiso . . . . . . . H21 H 0.4451 0.3447 0.5390 0.0533 1.0000 Uiso . . . . . . . H22 H 0.4513 0.3880 0.4021 0.0533 1.0000 Uiso . . . . . . . H31 H 0.2836 0.1433 0.4798 0.0467 1.0000 Uiso . . . . . . . H32 H 0.2899 0.1867 0.3428 0.0467 1.0000 Uiso . . . . . . . H51 H 0.3066 0.4925 0.6271 0.0436 1.0000 Uiso . . . . . . . H101 H -0.2358 0.2549 0.7038 0.0409 1.0000 Uiso . . . . . . . H171 H 0.0081 0.2098 0.3759 0.0343 1.0000 Uiso . . . . . . . H131 H -0.0593 -0.0044 0.3074 0.0395 1.0000 Uiso . . . . . . . H132 H -0.1359 0.1048 0.2106 0.0395 1.0000 Uiso . . . . . . . H141 H -0.2360 -0.1722 0.2463 0.0458 1.0000 Uiso . . . . . . . H142 H -0.1648 -0.1137 0.1348 0.0458 1.0000 Uiso . . . . . . . H151 H -0.5494 0.0101 0.1741 0.0481 1.0000 Uiso . . . . . . . H152 H -0.4702 -0.0991 0.2693 0.0481 1.0000 Uiso . . . . . . . H161 H -0.4433 0.1177 0.3490 0.0394 1.0000 Uiso . . . . . . . H162 H -0.3763 0.1811 0.2367 0.0394 1.0000 Uiso . . . . . . . H311 H -0.4081 -0.1206 0.0831 0.0473 1.0000 Uiso . . . . . . . H312 H -0.3562 0.0235 0.0746 0.0473 0.5000 Uiso . . . . . . . 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 0.022(3) 0.032(4) 0.057(5) -0.007(4) 0.019(3) 0.006(3) C2 0.021(3) 0.043(5) 0.070(6) -0.019(5) 0.014(4) 0.005(3) C3 0.027(5) 0.037(4) 0.053(5) -0.018(4) 0.012(4) 0.008(3) C4 0.019(3) 0.027(5) 0.035(4) -0.003(3) 0.006(3) 0.008(3) C5 0.023(4) 0.034(5) 0.051(5) -0.010(4) 0.002(3) 0.008(3) C6 0.035(4) 0.019(4) 0.045(4) -0.005(3) 0.002(3) 0.011(3) C7 0.046(3) 0.035(5) 0.061(5) -0.021(3) 0.006(3) 0.003(4) C8 0.032(4) 0.037(5) 0.046(4) -0.015(3) 0.007(3) 0.011(3) C9 0.026(4) 0.030(5) 0.043(4) -0.013(3) 0.011(3) 0.010(3) C10 0.027(4) 0.034(5) 0.042(5) -0.012(3) 0.015(3) 0.010(3) C11 0.019(4) 0.032(5) 0.043(4) -0.010(3) 0.011(3) 0.011(3) C12 0.018(3) 0.029(5) 0.039(4) -0.011(3) 0.007(2) 0.011(3) C13 0.021(4) 0.039(5) 0.038(5) -0.012(3) 0.011(3) 0.009(4) C14 0.032(4) 0.040(5) 0.043(5) -0.016(3) 0.014(3) 0.010(3) C15 0.025(4) 0.044(5) 0.051(5) -0.021(4) 0.012(3) 0.002(4) C16 0.016(3) 0.038(5) 0.043(5) -0.013(3) 0.006(3) 0.006(3) C17 0.023(4) 0.027(5) 0.036(4) -0.008(3) 0.013(3) 0.008(3) O1 0.042(3) 0.051(4) 0.090(5) -0.034(4) -0.005(3) 0.007(3) O2 0.068(3) 0.067(4) 0.063(4) -0.037(3) 0.020(3) -0.007(3) O3 0.053(4) 0.071(4) 0.054(3) -0.034(3) 0.018(2) -0.003(3) N1 0.018(3) 0.035(4) 0.046(4) -0.009(3) 0.009(2) 0.009(2) N2 0.018(3) 0.034(4) 0.038(4) -0.012(3) 0.009(2) 0.010(3) N3 0.030(3) 0.045(4) 0.043(4) -0.018(3) 0.010(2) 0.004(3) F1 0.024(2) 0.046(3) 0.056(3) -0.018(2) 0.018(2) 0.0039(19) Na1 0.056(4) 0.058(4) 0.051(3) -0.025(3) 0.011(3) 0.012(3) O101 0.176(9) 0.169(9) 0.099(7) 0.039(6) 0.084(7) 0.105(8) O102 0.085(6) 0.086(6) 0.109(6) -0.040(5) -0.012(5) 0.017(4) O103 0.084(6) 0.157(8) 0.107(7) 0.007(6) 0.057(5) 0.046(6) O104 0.047(4) 0.055(4) 0.062(4) -0.024(3) 0.003(3) 0.008(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.544(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.504(9) yes C1 . C3 . 1.477(8) yes C1 . N1 . 1.460(8) yes C1 . H11 . 0.950 no C2 . C3 . 1.497(9) yes C2 . H21 . 0.950 no C2 . H22 . 0.950 no C3 . H31 . 0.950 no C3 . H32 . 0.950 no C4 . C9 . 1.396(8) yes C4 . C17 . 1.396(8) yes C4 . N1 . 1.402(8) yes C5 . C6 . 1.359(9) yes C5 . N1 . 1.356(8) yes C5 . H51 . 0.950 no C6 . C7 . 1.503(8) yes C6 . C8 . 1.438(8) yes C7 . O1 . 1.259(8) yes C7 . O2 . 1.257(8) yes C8 . C9 . 1.461(8) yes C8 . O3 . 1.270(8) yes C9 . C10 . 1.390(8) yes C10 . C11 . 1.356(8) yes C10 . H101 . 0.950 no C11 . C12 . 1.419(8) yes C11 . F1 . 1.359(7) yes C12 . C17 . 1.384(8) yes C12 . N2 . 1.399(7) yes C13 . C14 . 1.498(9) yes C13 . N2 . 1.478(8) yes C13 . H131 . 0.950 no C13 . H132 . 0.950 no C14 . N3 . 1.483(8) yes C14 . H141 . 0.950 no C14 . H142 . 0.950 no C15 . C16 . 1.508(9) yes C15 . N3 . 1.489(8) yes C15 . H151 . 0.950 no C15 . H152 . 0.950 no C16 . N2 . 1.475(8) yes C16 . H161 . 0.950 no C16 . H162 . 0.950 no C17 . H171 . 0.950 no O2 . Na1 2_567 2.114(9) yes O2 . Na1 . 2.608(10) yes O3 . Na1 2_567 2.205(8) yes O3 . Na1 . 2.346(9) yes N3 . H311 . 0.880 no N3 . H312 . 0.880 no Na1 . O1000 . 2.141(12) yes Na1 . O1001 . 2.11(3) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C3 . C1 . C2 . 60.3(4) yes C3 . C1 . N1 . 118.4(6) yes C2 . C1 . N1 . 118.9(6) yes C3 . C1 . H11 . 115.9 no C2 . C1 . H11 . 116.0 no N1 . C1 . H11 . 116.0 no C1 . C3 . C2 . 60.7(4) yes C1 . C3 . H31 . 119.9 no C2 . C3 . H31 . 119.9 no C1 . C3 . H32 . 119.9 no C2 . C3 . H32 . 119.9 no H31 . C3 . H32 . 109.5 no C1 . C2 . C3 . 59.0(4) yes C1 . C2 . H21 . 120.2 no C3 . C2 . H21 . 120.2 no C1 . C2 . H22 . 120.2 no C3 . C2 . H22 . 120.2 no H21 . C2 . H22 . 109.5 no C9 . C4 . C17 . 120.5(5) yes C9 . C4 . N1 . 118.3(5) yes C17 . C4 . N1 . 121.1(5) yes C6 . C5 . N1 . 124.6(6) yes C6 . C5 . H51 . 117.7 no N1 . C5 . H51 . 117.7 no C5 . C6 . C7 . 116.3(5) yes C5 . C6 . C8 . 119.5(5) yes C7 . C6 . C8 . 124.1(5) yes C6 . C7 . O1 . 117.9(6) yes C6 . C7 . O2 . 117.6(6) yes O1 . C7 . O2 . 124.5(6) yes C6 . C8 . C9 . 115.6(5) yes C6 . C8 . O3 . 124.9(6) yes C9 . C8 . O3 . 119.6(6) yes C8 . C9 . C4 . 122.2(5) yes C8 . C9 . C10 . 119.4(5) yes C4 . C9 . C10 . 118.5(5) yes C9 . C10 . C11 . 120.5(5) yes C9 . C10 . H101 . 119.8 no C11 . C10 . H101 . 119.8 no C10 . C11 . C12 . 122.7(5) yes C10 . C11 . F1 . 119.0(5) yes C12 . C11 . F1 . 118.2(5) yes C11 . C12 . C17 . 116.4(5) yes C11 . C12 . N2 . 119.4(5) yes C17 . C12 . N2 . 124.1(5) yes C14 . C13 . N2 . 109.8(5) yes C14 . C13 . H131 . 109.4 no N2 . C13 . H131 . 109.4 no C14 . C13 . H132 . 109.4 no N2 . C13 . H132 . 109.4 no H131 . C13 . H132 . 109.5 no C13 . C14 . N3 . 111.0(6) yes C13 . C14 . H141 . 109.1 no N3 . C14 . H141 . 109.0 no C13 . C14 . H142 . 109.1 no N3 . C14 . H142 . 109.1 no H141 . C14 . H142 . 109.5 no C16 . C15 . N3 . 109.9(6) yes C16 . C15 . H151 . 109.4 no N3 . C15 . H151 . 109.4 no C16 . C15 . H152 . 109.4 no N3 . C15 . H152 . 109.3 no H151 . C15 . H152 . 109.5 no C15 . C16 . N2 . 110.9(5) yes C15 . C16 . H161 . 109.1 no N2 . C16 . H161 . 109.1 no C15 . C16 . H162 . 109.1 no N2 . C16 . H162 . 109.1 no H161 . C16 . H162 . 109.5 no C4 . C17 . C12 . 121.4(5) yes C4 . C17 . H171 . 119.3 no C12 . C17 . H171 . 119.3 no Na1 2_567 O2 . C7 . 135.3(5) yes C7 . O2 . Na1 . 115.4(6) yes Na1 2_567 O3 . C8 . 129.0(5) yes C8 . O3 . Na1 . 130.2(5) yes C1 . N1 . C4 . 119.2(5) yes C1 . N1 . C5 . 120.9(5) yes C4 . N1 . C5 . 119.9(5) yes C13 . N2 . C16 . 110.6(5) yes C13 . N2 . C12 . 116.3(5) yes C16 . N2 . C12 . 115.8(5) yes C15 . N3 . C14 . 108.5(5) yes C15 . N3 . H311 . 109.7 no C14 . N3 . H311 . 109.7 no C15 . N3 . H312 . 109.7 no C14 . N3 . H312 . 109.7 no H311 . N3 . H312 . 109.5 no O3 . Na1 . O3 2_567 144.7(3) yes O3 . Na1 . O2 2_567 100.0(3) yes O3 2_567 Na1 . O2 2_567 81.9(3) yes O3 . Na1 . O2 . 69.5(3) yes O3 2_567 Na1 . O2 . 90.2(3) yes O2 2_567 Na1 . O2 . 148.0(3) yes O3 . Na1 . O1000 . 110.6(4) yes O3 2_567 Na1 . O1000 . 103.6(4) yes O2 2_567 Na1 . O1000 . 99.6(4) yes O2 . Na1 . O1000 . 112.4(4) yes O3 . Na1 . O3 2_567 144.7(3) yes O3 . Na1 . O2 2_567 100.0(3) yes O3 2_567 Na1 . O2 2_567 81.9(3) yes O3 . Na1 . O2 . 69.5(3) yes O3 2_567 Na1 . O2 . 90.2(3) yes O2 2_567 Na1 . O2 . 148.0(3) yes O3 . Na1 . O1001 . 121.6(9) yes O3 2_567 Na1 . O1001 . 72.8(9) yes O2 2_567 Na1 . O1001 . 135.7(9) yes O2 . Na1 . O1001 . 68.9(9) yes #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 714347' #Cf Na crysatllised at 0.6 GPa, data collected at 0.2 GPa _cell_length_a 9.547(7) _cell_length_b 9.870(7) _cell_length_c 11.109(12) _cell_angle_alpha 88.79(4) _cell_angle_beta 101.42(4) _cell_angle_gamma 90.25(2) _cell_volume 1025.8(15) _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 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Na 0.0362 0.0249 4.7626 3.2850 3.1736 8.8422 1.2674 0.3136 1.1128 129.4240 0.6760 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 _chemical_formula_sum 'C17 H27 F1 N3 Na1 O8' _chemical_formula_moiety 'C17 H17 F N3 O3, 5(H2 O), NA' _chemical_compound_source ; high-pressure crystallisation at 0.6 GPa ; _chemical_formula_weight 443.40 _cell_measurement_reflns_used 1126 _cell_measurement_theta_min 3 _cell_measurement_theta_max 16 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_max 0.25 _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.137 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'based on symmetry-related measuraments' # SHADE (Parsons, 2004) # SADABS (Siemens, 1996) # The following data are from Sadabs: _exptl_absorpt_correction_T_min 0.77 _exptl_absorpt_correction_T_max 0.99 # Sheldrick geometric approximatio 0.99 0.99 _diffrn_measurement_device 'Bruker Apex2' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution SHELXM _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003), PLATON, XCIF, ENCIFER' _computing_molecular_graphics MERCURY _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 293 _diffrn_reflns_number 5367 _reflns_number_total 701 _diffrn_reflns_av_R_equivalents 0.0402 # Number of reflections with Friedels Law is 701 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1815 _diffrn_reflns_theta_min 2.064 _diffrn_reflns_theta_max 19.631 _diffrn_measured_fraction_theta_max 0.387 _diffrn_reflns_theta_full 14.723 _diffrn_measured_fraction_theta_full 0.555 _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #_diffrn_reflns_limit_h_max 8 #_diffrn_reflns_limit_h_min -8 #_diffrn_reflns_limit_k_max 9 #_diffrn_reflns_limit_k_min -8 #_diffrn_reflns_limit_l_max 7 #_diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 7 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min -8 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 7 _oxford_diffrn_Wilson_B_factor 3.21 _oxford_diffrn_Wilson_scale 2.22 _atom_sites_solution_primary 'molecular replacement' _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.46 _refine_diff_density_max 0.44 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 698 _refine_ls_number_restraints 66 _refine_ls_number_parameters 121 _oxford_refine_ls_R_factor_ref 0.0960 _refine_ls_wR_factor_ref 0.1830 _refine_ls_goodness_of_fit_ref 1.0043 _refine_ls_shift/su_max 0.000079 # The values computed from all data _oxford_reflns_number_all 698 _refine_ls_R_factor_all 0.0960 _refine_ls_wR_factor_all 0.1830 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 548 _refine_ls_R_factor_gt 0.0780 _refine_ls_wR_factor_gt 0.1741 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.06P)^2^ +10.98P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_special_details ; The Following ALERTS were generated by PLATON checkcif<<< 022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.39 023_ALERT_3_A Resolution (too) Low [sin(th)/Lambda < 0.6]..... 19.63 Deg. 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 14.72 Deg. 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.56 088_ALERT_3_A Poor Data / Parameter Ratio .................... 5.77 340_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ... 15 148_ALERT_3_B su on the c - Axis is Too Large (x 1000) . 12 Ang. 061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.80 These alerts are not uncommon for high-pressure data and indicate that the structure quality is not high. The geometry of the diamond-anvil cell severely restricts the amount of recirpocal space that can be accessed, resulting in a poor completeness. This is more evident for lower-symmetry crystal systems (triclinic in this case). The data is not only incomplete but also weak, as testified by diffraction to a maximum d of 1.0 A. The use of restraints, 66 in total, increases the data to parameter ratio to 6.3. Related to the use of restraints, we note tat the calculation of bond precision by the Checkcif procedure does not take into account the off diagonal terms of the variance-covariance matrix. 201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) ....... 28 210_ALERT_3_B No Anisotropic ADP's Found in CIF .............. ? 202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent ......... 2 All non-H-atoms were refined with isotropic thermal parameters 306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O103 306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O104 430_ALERT_2_B Short Inter D...A Contact O1 .. O101 .. 2.77 Ang. 430_ALERT_2_B Short Inter D...A Contact O1 .. O102 .. 2.78 Ang. 430_ALERT_2_B Short Inter D...A Contact O2 .. O104 .. 2.67 Ang. 430_ALERT_2_B Short Inter D...A Contact O103 .. O104 .. 2.78 Ang. 430_ALERT_2_C Short Inter D...A Contact O100 .. O103 .. 2.87 Ang. No information could be inferred from the data about the position of water H-atoms and given the intricated network of H-bonding pattern, no water H-atoms were placed geometrically. 041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? 042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? 043_ALERT_1_C Check Reported Molecular Weight ................ 443.40 044_ALERT_1_C Calculated and Reported Dx Differ .............. ? 045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio 068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? The formulae given and derived properties are correct. Although no water H-atoms are present in the model, these were included for the calculation of formulae, molecular weight, density, mu and F000. 155_ALERT_4_C The Triclinic Unitcell is NOT Reduced .......... ? The cell was chose to facilitate comparision with the known structure of Cf hexahydrate, CSD ref. code COVPIN and the other structures presented in this work. 731_ALERT_1_C Bond Calc 1.457(14), Rep 1.457(6) ...... 2.33 su-Ra C1 -C3 1.555 1.555 731_ALERT_1_C Bond Calc 1.500(17), Rep 1.500(8) ...... 2.13 su-Ra C3 -C2 1.555 1.555 860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 66 These alerts stem from the fact that PLATON calculates e.s.d.s using only the variances whereas CRYSTALS uses the full variance/covariance matrix. Soft restraints were used on all bond lengths and angles of the Cf moiety. 790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 O 790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 O Noted, no action taken. The centre of gravity of the main Cf moiety is within the unit cell. Water O-atoms were transformed to give a clear picture of the coordination environment of the Cf moiety. 199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K 200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K Data were collected at room temperature ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens C1 C 0.2304(10) 0.3520(9) 0.4305(11) 0.031(4) 1.0000 Uiso D . . . . . . C3 C 0.2947(13) 0.2217(9) 0.4145(18) 0.042(5) 1.0000 Uiso D . . . . . . C2 C 0.3895(10) 0.3422(12) 0.4481(19) 0.050(5) 1.0000 Uiso D . . . . . . C4 C 0.0380(9) 0.3090(10) 0.5479(10) 0.019(4) 1.0000 Uiso D . . . . . . C5 C 0.2319(10) 0.4533(11) 0.6300(11) 0.026(4) 1.0000 Uiso D . . . . . . C6 C 0.1826(9) 0.4789(10) 0.7359(10) 0.029(4) 1.0000 Uiso D . . . . . . C7 C 0.2697(9) 0.5730(11) 0.8277(11) 0.031(4) 1.0000 Uiso D . . . . . . C8 C 0.0545(10) 0.4121(11) 0.7563(9) 0.030(4) 1.0000 Uiso D . . . . . . C9 C -0.0184(9) 0.3304(10) 0.6536(10) 0.021(4) 1.0000 Uiso D . . . . . . C10 C -0.1473(11) 0.2647(11) 0.6633(11) 0.036(4) 1.0000 Uiso D . . . . . . C11 C -0.2111(9) 0.1821(11) 0.5714(10) 0.027(4) 1.0000 Uiso D . . . . . . C12 C -0.1576(9) 0.1583(10) 0.4635(10) 0.026(4) 1.0000 Uiso D . . . . . . C13 C -0.1484(11) 0.0277(11) 0.2813(13) 0.035(4) 1.0000 Uiso D . . . . . . C14 C -0.2238(11) -0.0887(12) 0.2075(14) 0.043(5) 1.0000 Uiso D . . . . . . C15 C -0.4491(11) -0.0160(12) 0.2489(14) 0.047(5) 1.0000 Uiso D . . . . . . C16 C -0.3766(10) 0.1003(11) 0.3224(14) 0.043(5) 1.0000 Uiso D . . . . . . C17 C -0.0314(10) 0.2242(11) 0.4539(11) 0.027(4) 1.0000 Uiso D . . . . . . O1 O 0.3993(9) 0.5885(8) 0.8208(13) 0.043(3) 1.0000 Uiso D . . . . . . O2 O 0.2088(9) 0.6334(8) 0.9022(12) 0.046(3) 1.0000 Uiso D . . . . . . O3 O 0.0061(9) 0.4222(8) 0.8535(11) 0.042(3) 1.0000 Uiso D . . . . . . N1 N 0.1672(8) 0.3717(9) 0.5386(9) 0.030(3) 1.0000 Uiso D . . . . . . N2 N -0.2269(8) 0.0662(8) 0.3768(10) 0.031(3) 1.0000 Uiso D . . . . . . N3 N -0.3713(10) -0.0482(10) 0.1494(12) 0.041(4) 1.0000 Uiso D . . . . . . F1 F -0.3303(7) 0.1133(7) 0.5881(11) 0.050(3) 1.0000 Uiso D . . . . . . Na1 Na 0.1775(6) 0.4749(5) 1.0602(9) 0.0453(19) 1.0000 Uiso . . . . . . . O100 O 0.0760(10) 0.2833(10) 1.1441(17) 0.057(3) 1.0000 Uiso . . . . . . . O101 O 0.3882(11) 0.5985(10) 1.1899(17) 0.061(3) 1.0000 Uiso . . . . . . . O102 O 0.3578(11) 0.3069(10) 1.0301(18) 0.068(4) 1.0000 Uiso . . . . . . . O103 O 0.1240(14) 0.0022(13) 1.106(2) 0.100(4) 1.0000 Uiso . . . . . . . O104 O -0.3291(10) 0.1526(9) -0.0256(16) 0.051(3) 1.0000 Uiso . . . . . . . H11 H 0.1852 0.3979 0.3577 0.0398 1.0000 Uiso . . . . . . . H21 H 0.4480 0.3468 0.5288 0.0630 1.0000 Uiso . . . . . . . H22 H 0.4395 0.3825 0.3909 0.0630 1.0000 Uiso . . . . . . . H31 H 0.2925 0.1501 0.4722 0.0510 1.0000 Uiso . . . . . . . H32 H 0.2840 0.1858 0.3343 0.0510 1.0000 Uiso . . . . . . . H51 H 0.3183 0.4966 0.6201 0.0335 1.0000 Uiso . . . . . . . H101 H -0.1886 0.2775 0.7331 0.0482 1.0000 Uiso . . . . . . . H171 H 0.0097 0.2108 0.3835 0.0333 1.0000 Uiso . . . . . . . H131 H -0.0543 0.0015 0.3186 0.0449 1.0000 Uiso . . . . . . . H132 H -0.1450 0.1037 0.2277 0.0449 1.0000 Uiso . . . . . . . H141 H -0.2267 -0.1650 0.2612 0.0576 1.0000 Uiso . . . . . . . H142 H -0.1726 -0.1122 0.1460 0.0576 1.0000 Uiso . . . . . . . H151 H -0.5448 0.0084 0.2139 0.0611 1.0000 Uiso . . . . . . . H152 H -0.4490 -0.0932 0.3017 0.0611 1.0000 Uiso . . . . . . . H161 H -0.4265 0.1194 0.3866 0.0561 1.0000 Uiso . . . . . . . H162 H -0.3787 0.1779 0.2704 0.0561 1.0000 Uiso . . . . . . . H311 H -0.4146 -0.1155 0.1061 0.0529 1.0000 Uiso . . . . . . . _refine_ls_extinction_coef 64.740 _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 1.90(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.496(8) yes C1 . C3 . 1.457(6) yes C1 . N1 . 1.463(9) yes C1 . H11 . 0.946 no C2 . C3 . 1.500(8) yes C2 . H21 . 0.960 no C2 . H22 . 0.947 no C3 . H31 . 0.947 no C3 . H32 . 0.952 no C4 . C9 . 1.406(8) yes C4 . C17 . 1.410(9) yes C4 . N1 . 1.399(7) yes C5 . C6 . 1.380(9) yes C5 . N1 . 1.358(9) yes C5 . H51 . 0.951 no C6 . C7 . 1.514(9) yes C6 . C8 . 1.441(8) yes C7 . O1 . 1.263(7) yes C7 . O2 . 1.262(8) yes C8 . C9 . 1.468(8) yes C8 . O3 . 1.262(8) yes C9 . C10 . 1.411(8) yes C10 . C11 . 1.364(9) yes C10 . H101 . 0.949 no C11 . C12 . 1.418(8) yes C11 . F1 . 1.364(7) yes C12 . C17 . 1.388(8) yes C12 . N2 . 1.403(8) yes C13 . C14 . 1.519(9) yes C13 . N2 . 1.471(9) yes C13 . H131 . 0.946 no C13 . H132 . 0.953 no C14 . N3 . 1.481(9) yes C14 . H141 . 0.955 no C14 . H142 . 0.947 no C15 . C16 . 1.508(9) yes C15 . N3 . 1.489(9) yes C15 . H151 . 0.949 no C15 . H152 . 0.952 no C16 . N2 . 1.475(8) yes C16 . H161 . 0.954 no C16 . H162 . 0.947 no C17 . H171 . 0.954 no O2 . Na1 . 2.389(12) yes O3 . Na1 2_567 2.397(10) yes O3 . Na1 . 2.603(16) yes N3 . H311 . 0.882 no Na1 . O100 . 2.377(10) yes Na1 . O101 . 2.552(18) yes Na1 . O102 . 2.470(11) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C3 . C1 . C2 . 61.0(4) yes C3 . C1 . N1 . 119.1(8) yes C2 . C1 . N1 . 118.4(8) yes C3 . C1 . H11 . 116.0 no C2 . C1 . H11 . 115.0 no N1 . C1 . H11 . 116.1 no C1 . C3 . C2 . 60.8(4) yes C1 . C3 . H31 . 120.1 no C2 . C3 . H31 . 120.4 no C1 . C3 . H32 . 119.4 no C2 . C3 . H32 . 119.4 no H31 . C3 . H32 . 109.5 no C3 . C2 . C1 . 58.2(4) yes C3 . C2 . H21 . 119.7 no C1 . C2 . H21 . 120.4 no C3 . C2 . H22 . 120.9 no C1 . C2 . H22 . 121.3 no H21 . C2 . H22 . 108.8 no C9 . C4 . C17 . 121.3(5) yes C9 . C4 . N1 . 118.5(5) yes C17 . C4 . N1 . 120.2(6) yes C6 . C5 . N1 . 125.3(6) yes C6 . C5 . H51 . 117.3 no N1 . C5 . H51 . 117.3 no C5 . C6 . C7 . 117.8(6) yes C5 . C6 . C8 . 119.1(6) yes C7 . C6 . C8 . 123.1(5) yes C6 . C7 . O1 . 116.5(6) yes C6 . C7 . O2 . 119.0(6) yes O1 . C7 . O2 . 124.5(7) yes C6 . C8 . C9 . 114.7(5) yes C6 . C8 . O3 . 123.8(6) yes C9 . C8 . O3 . 121.5(6) yes C8 . C9 . C4 . 122.9(5) yes C8 . C9 . C10 . 118.9(6) yes C4 . C9 . C10 . 118.1(6) yes C9 . C10 . C11 . 119.2(6) yes C9 . C10 . H101 . 120.2 no C11 . C10 . H101 . 120.6 no C10 . C11 . C12 . 124.3(5) yes C10 . C11 . F1 . 117.4(6) yes C12 . C11 . F1 . 118.3(6) yes C11 . C12 . C17 . 116.3(6) yes C11 . C12 . N2 . 120.2(5) yes C17 . C12 . N2 . 123.5(6) yes C14 . C13 . N2 . 110.2(7) yes C14 . C13 . H131 . 109.8 no N2 . C13 . H131 . 109.4 no C14 . C13 . H132 . 109.0 no N2 . C13 . H132 . 108.8 no H131 . C13 . H132 . 109.5 no C13 . C14 . N3 . 109.9(9) yes C13 . C14 . H141 . 109.0 no N3 . C14 . H141 . 109.6 no C13 . C14 . H142 . 109.5 no N3 . C14 . H142 . 109.7 no H141 . C14 . H142 . 109.3 no C16 . C15 . N3 . 109.7(7) yes C16 . C15 . H151 . 109.3 no N3 . C15 . H151 . 109.6 no C16 . C15 . H152 . 109.2 no N3 . C15 . H152 . 109.6 no H151 . C15 . H152 . 109.4 no C15 . C16 . N2 . 110.7(7) yes C15 . C16 . H161 . 109.1 no N2 . C16 . H161 . 109.2 no C15 . C16 . H162 . 109.3 no N2 . C16 . H162 . 109.3 no H161 . C16 . H162 . 109.3 no C4 . C17 . C12 . 120.8(6) yes C4 . C17 . H171 . 119.6 no C12 . C17 . H171 . 119.6 no C7 . O2 . Na1 . 108.1(8) yes Na1 2_567 O3 . C8 . 143.7(9) yes Na1 2_567 O3 . Na1 . 86.3(4) yes C8 . O3 . Na1 . 120.2(6) yes C1 . N1 . C4 . 120.5(6) yes C1 . N1 . C5 . 120.3(6) yes C4 . N1 . C5 . 119.2(6) yes C16 . N2 . C13 . 110.9(7) yes C16 . N2 . C12 . 114.8(6) yes C13 . N2 . C12 . 116.0(6) yes C15 . N3 . C14 . 108.0(7) yes C15 . N3 . H311 . 109.5 no C14 . N3 . H311 . 109.7 no O2 . Na1 . O3 2_567 102.9(3) yes O2 . Na1 . O3 . 68.8(4) yes O3 2_567 Na1 . O3 . 93.7(4) yes O2 . Na1 . O100 . 155.5(7) yes O3 2_567 Na1 . O100 . 78.4(4) yes O3 . Na1 . O100 . 86.7(5) yes O2 . Na1 . O101 . 84.5(4) yes O3 2_567 Na1 . O101 . 96.9(5) yes O3 . Na1 . O101 . 152.9(5) yes O100 . Na1 . O101 . 119.8(6) yes O2 . Na1 . O102 . 98.1(5) yes O3 2_567 Na1 . O102 . 159.0(5) yes O3 . Na1 . O102 . 93.9(6) yes O100 . Na1 . O102 . 82.5(4) yes O101 . Na1 . O102 . 85.0(5) yes #===END data_5 _database_code_depnum_ccdc_archive 'CCDC 714348' #Cf Na salt recovered to ambient pressure and #measure a first time at 100 K _cell_length_a 11.065(10) _cell_length_b 13.155(12) _cell_length_c 13.879(12) _cell_angle_alpha 90.983(14) _cell_angle_beta 98.941(14) _cell_angle_gamma 93.181(14) _cell_volume 1992(3) _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 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Na 0.0362 0.0249 4.7626 3.2850 3.1736 8.8422 1.2674 0.3136 1.1128 129.4240 0.6760 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 _chemical_formula_sum 'C34 H54 F2 N6 Na2 O16' _chemical_formula_moiety '2(C17 H17 F N3 O3), 10(H2 O), 2(Na)' _chemical_compound_source ; recovery of 4 to ambient pressure, first 100 K data collection ; _chemical_formula_weight 858.65 _cell_measurement_reflns_used 937 _cell_measurement_theta_min 3 _cell_measurement_theta_max 19 _cell_measurement_temperature 100 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_max 0.15 _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.140 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'based on symmetry-related measuraments' # SADABS (Siemens, 1996) # The following data are from Sadabs: _exptl_absorpt_correction_T_min 0.52 _exptl_absorpt_correction_T_max 0.99 # Sheldrick geometric approximatio 0.99 0.99 _diffrn_measurement_device 'Bruker Apex2' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'Starting from fract. coordinates of 4' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003), PLATON, XCIF, ENCIFER' _computing_molecular_graphics MERCURY _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 100 _diffrn_reflns_number 7961 _reflns_number_total 3173 _diffrn_reflns_av_R_equivalents 0.109 # Number of reflections with Friedels Law is 3173 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3239 _diffrn_reflns_theta_min 1.486 _diffrn_reflns_theta_max 19.063 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 18.682 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _reflns_limit_h_min -10 _reflns_limit_h_max 9 _reflns_limit_k_min -11 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 12 _oxford_diffrn_Wilson_B_factor 1.56 _oxford_diffrn_Wilson_scale 30.15 _atom_sites_solution_primary ; 'Starting from fract. coordinates of 4' ; # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.90 _refine_diff_density_max 1.22 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 3164 _refine_ls_number_restraints 200 _refine_ls_number_parameters 273 _oxford_refine_ls_R_factor_ref 0.1919 _refine_ls_wR_factor_ref 0.3717 _refine_ls_goodness_of_fit_ref 0.9484 _refine_ls_shift/su_max 0.000385 # The values computed from all data _oxford_reflns_number_all 3164 _refine_ls_R_factor_all 0.1919 _refine_ls_wR_factor_all 0.3717 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1608 _refine_ls_R_factor_gt 0.1206 _refine_ls_wR_factor_gt 0.3214 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.17P)^2^ +28.92P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_special_details ; The Following ALERTS were generated by PLATON checkcif<<< 023_ALERT_3_A Resolution (too) Low [sin(th)/Lambda < 0.6]..... 19.06 Deg. 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 18.68 Deg. 061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.53 084_ALERT_2_B High R2 Value .................................. 0.37 097_ALERT_2_B Maximum (Positive) Residual Density ............ 1.22 e/A** 201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ....... 1 202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent ......... 1 020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11 082_ALERT_2_C High R1 Value .................................. 0.12 098_ALERT_2_C Minimum (Negative) Residual Density ............ -0.90 e/A** These alerts indicate that the structure quality is low. However, this is the best structure we could obtain from the data collected on this small, weakly diffracting crystal recovered at ambient pressure. Data were collected at low temperature, with high counting time and with a laboratory X-ray source. The low crystal quality was also reflected in the broad and split reflection profiles. In addition, the supercell reflections were weak. This is not surprising given that the structure has a high degree of pseudo symmetry in that the Cf moieties are related by an inversion centre. The data were cut to 1.1 A for integration as no significan scattering was observed for this small crystal at higher resolution. The dataset is essentially complete to 1.1 A as shown below: #=============================================================================== Resolution & Completeness Statistics (Cumulative) #=============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------- 19.06 0.460 0.982 3232 3173 59 #------------------------------------------------------------------------------- 213_ALERT_2_C Atom Na1 has ADP max/min Ratio ............. 4.00 prola 213_ALERT_2_C Atom Na2 has ADP max/min Ratio ............. 3.70 prola 213_ALERT_2_C Atom C25 has ADP max/min Ratio ............. 3.30 prola 250_ALERT_2_B Large U3/U1 Ratio for Average U(i,j) Tensor .... 4.35 The TLS formalism was used to constrain anisotropic thermal parameters. The use of this formalism for curing of ill-defined anisotropic thermal parameters is well known. The poor quality of the data (small crysta, reflection splitting, weak supercell reflections, low resolution) will contribute to the tensors distortions, though these are considerably less prominent than in a full independent refinement of anisotropic thermal parameters. Large values of the U3/U1 ratio can also indicate possible systematic errors in the data that have not been corrected for and the need for a better absorption correction. We have processed the data to the best of our knowledge. 306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O104 306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O107 306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O108 306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O109 430_ALERT_2_A Short Inter D...A Contact O1031 .. O1031 .. 2.47 Ang. 430_ALERT_2_A Short Inter D...A Contact O1050 .. O104 .. 2.48 Ang. 430_ALERT_2_A Short Inter D...A Contact O1051 .. O108 .. 2.43 Ang 430_ALERT_2_B Short Inter D...A Contact O1 .. O108 .. 2.66 Ang. 430_ALERT_2_B Short Inter D...A Contact O1 .. O106 .. 2.73 Ang. 430_ALERT_2_B Short Inter D...A Contact O2 .. O107 .. 2.75 Ang. 430_ALERT_2_B Short Inter D...A Contact O1031 .. O107 .. 2.68 Ang. 430_ALERT_2_B Short Inter D...A Contact O4 .. O101 .. 2.78 Ang. 430_ALERT_2_B Short Inter D...A Contact O4 .. O102 .. 2.81 Ang. 430_ALERT_2_B Short Inter D...A Contact O5 .. O109 .. 2.78 Ang. 430_ALERT_2_B Short Inter D...A Contact O100 .. O1030 .. 2.68 Ang. 430_ALERT_2_B Short Inter D...A Contact O104 .. O109 .. 2.76 Ang. 430_ALERT_2_B Short Inter D...A Contact O106 .. O107 .. 2.70 Ang. 430_ALERT_2_B Short Inter D...A Contact O107 .. O1030 .. 2.61 Ang. 430_ALERT_2_C Short Inter D...A Contact O1031 .. O100 .. 2.87 Ang. 311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ..... >O1031 311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ..... Apex2, Version 2 User Manual, M86-E01078, Madison, WI. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens N1 N 0.5363(7) 0.7582(5) 0.3990(7) 0.0334 1.0000 Uani D . . . . . . N2 N 0.3626(6) 0.4101(5) 0.3459(5) 0.0380 1.0000 Uani D . . . . . . N3 N 0.1311(7) 0.2938(8) 0.3327(7) 0.0387 1.0000 Uani D . . . . . . C1 C 0.4305(7) 0.7881(7) 0.4419(6) 0.0416 1.0000 Uani D . . . . . . C2 C 0.4473(10) 0.8636(9) 0.5246(9) 0.0422 1.0000 Uani D . . . . . . C3 C 0.4181(12) 0.7529(9) 0.5402(8) 0.0439 1.0000 Uani D . . . . . . C4 C 0.5430(8) 0.6586(6) 0.3638(9) 0.0268 1.0000 Uani D . . . . . . C5 C 0.6275(10) 0.8286(6) 0.3887(10) 0.0345 1.0000 Uani D . . . . . . C6 C 0.7313(8) 0.8090(6) 0.3495(9) 0.0323 1.0000 Uani D . . . . . . C7 C 0.8269(10) 0.8966(7) 0.3516(9) 0.0455 1.0000 Uani D . . . . . . C8 C 0.7432(8) 0.7097(6) 0.3088(10) 0.0317 1.0000 Uani D . . . . . . C9 C 0.6425(8) 0.6347(6) 0.3181(9) 0.0271 1.0000 Uani D . . . . . . C10 C 0.6474(9) 0.5349(7) 0.2822(10) 0.0311 1.0000 Uani D . . . . . . C11 C 0.5561(8) 0.4636(6) 0.2939(10) 0.0289 1.0000 Uani D . . . . . . C12 C 0.4520(7) 0.4869(5) 0.3365(8) 0.0259 1.0000 Uani D . . . . . . C13 C 0.2691(9) 0.4364(7) 0.4070(8) 0.0384 1.0000 Uani D . . . . . . C14 C 0.1941(10) 0.3417(8) 0.4249(6) 0.0388 1.0000 Uani D . . . . . . C15 C 0.2252(10) 0.2637(7) 0.2745(8) 0.0383 1.0000 Uani D . . . . . . C16 C 0.3039(9) 0.3557(9) 0.2532(6) 0.0379 1.0000 Uani D . . . . . . C17 C 0.4475(8) 0.5857(7) 0.3707(9) 0.0276 1.0000 Uani D . . . . . . O1 O 0.8220(9) 0.9679(8) 0.4132(8) 0.0566 1.0000 Uani D . . . . . . O2 O 0.9023(10) 0.8950(7) 0.2926(8) 0.0566 1.0000 Uani D . . . . . . O3 O 0.8332(8) 0.6829(6) 0.2717(7) 0.0415 1.0000 Uani D . . . . . . F1 F 0.5672(7) 0.3671(6) 0.2623(6) 0.0399 1.0000 Uani D . . . . . . N4 N 1.4687(8) 0.7413(6) 0.1090(7) 0.0360 1.0000 Uani D . . . . . . N5 N 1.6582(7) 1.0906(6) 0.1472(6) 0.0370 1.0000 Uani D . . . . . . N6 N 1.8806(8) 1.2140(8) 0.1381(8) 0.0401 1.0000 Uani D . . . . . . C18 C 1.5684(8) 0.7067(7) 0.0633(7) 0.0419 1.0000 Uani D . . . . . . C19 C 1.5430(11) 0.6329(9) -0.0211(10) 0.0443 1.0000 Uani D . . . . . . C20 C 1.5803(12) 0.7427(9) -0.0352(8) 0.0401 1.0000 Uani D . . . . . . C21 C 1.4687(9) 0.8431(6) 0.1431(10) 0.0339 1.0000 Uani D . . . . . . C22 C 1.3744(10) 0.6753(7) 0.1213(10) 0.0379 1.0000 Uani D . . . . . . C23 C 1.2769(8) 0.6992(7) 0.1664(9) 0.0377 1.0000 Uani D . . . . . . C24 C 1.1740(9) 0.6150(7) 0.1656(9) 0.0393 1.0000 Uani D . . . . . . C25 C 1.2717(9) 0.8004(6) 0.2042(10) 0.0395 1.0000 Uani D . . . . . . C26 C 1.3751(9) 0.8720(6) 0.1892(10) 0.0357 1.0000 Uani D . . . . . . C27 C 1.3765(10) 0.9735(8) 0.2229(10) 0.0386 1.0000 Uani D . . . . . . C28 C 1.4704(9) 1.0415(7) 0.2076(10) 0.0379 1.0000 Uani D . . . . . . C29 C 1.5673(8) 1.0143(6) 0.1630(8) 0.0340 1.0000 Uani D . . . . . . C30 C 1.7402(10) 1.0642(7) 0.0784(8) 0.0345 1.0000 Uani D . . . . . . C31 C 1.8082(11) 1.1609(9) 0.0510(7) 0.0378 1.0000 Uani D . . . . . . C32 C 1.7951(11) 1.2387(7) 0.2080(8) 0.0410 1.0000 Uani D . . . . . . C33 C 1.7266(10) 1.1434(9) 0.2348(7) 0.0389 1.0000 Uani D . . . . . . C34 C 1.5661(9) 0.9139(8) 0.1299(10) 0.0329 1.0000 Uani D . . . . . . O4 O 1.1812(8) 0.5360(8) 0.1124(7) 0.0439 1.0000 Uani D . . . . . . O5 O 1.0909(8) 0.6281(7) 0.2153(7) 0.0431 1.0000 Uani D . . . . . . O6 O 1.1872(10) 0.8318(7) 0.2452(8) 0.0547 1.0000 Uani D . . . . . . F2 F 1.4649(7) 1.1408(6) 0.2379(6) 0.0428 1.0000 Uani D . . . . . . O100 O 0.8596(9) 0.8130(9) 0.1038(8) 0.0536 1.0000 Uani . . . . . . . O101 O 0.7994(9) 0.4825(8) 0.0841(8) 0.042(3) 1.0000 Uiso . . . . . . . O102 O 0.9518(11) 0.6474(10) -0.0474(8) 0.0617 1.0000 Uani . . . . . . . O1030 O 0.888(4) 0.894(3) -0.068(3) 0.082(13) 0.4000 Uiso . . . 1 1 . . O1031 O 0.911(2) 0.9499(19) -0.0456(16) 0.064(7) 0.6000 Uiso . . . 1 2 . . O104 O 0.8957(13) 0.4519(14) 0.4335(12) 0.1169 1.0000 Uani . . . . . . . O1050 O 1.106(2) 0.707(2) 0.4727(16) 0.040(7) 0.5000 Uiso . . . . . . . O1051 O 1.0916(19) 0.762(2) 0.4737(15) 0.032(7) 0.5000 Uiso . . . . . . . O106 O 0.225(3) 0.009(2) 0.400(2) 0.094(10) 0.5000 Uiso . . . . . . . O107 O 0.0693(13) 0.0350(11) 0.2350(9) 0.0898 1.0000 Uani . . . . . . . O108 O 0.9998(16) 0.8856(12) 0.5679(10) 0.1120 1.0000 Uani . . . . . . . O109 O 0.9767(10) 0.4434(9) 0.2555(8) 0.0510 1.0000 Uani . . . . . . . Na1 Na 1.0336(5) 0.7546(5) 0.3086(5) 0.0513 1.0000 Uani . . . . . . . Na2 Na 0.9021(5) 0.6438(5) 0.1104(4) 0.0421 1.0000 Uani . . . . . . . H11 H 0.3560 0.7904 0.3977 0.0509 1.0000 Uiso . . . . . . . H21 H 0.5265 0.8937 0.5488 0.0512 1.0000 Uiso . . . . . . . H22 H 0.3876 0.9119 0.5290 0.0512 1.0000 Uiso . . . . . . . H31 H 0.4787 0.7128 0.5745 0.0513 1.0000 Uiso . . . . . . . H32 H 0.3398 0.7310 0.5548 0.0513 1.0000 Uiso . . . . . . . H51 H 0.6192 0.8965 0.4101 0.0414 1.0000 Uiso . . . . . . . H101 H 0.7134 0.5169 0.2502 0.0374 1.0000 Uiso . . . . . . . H131 H 0.3090 0.4654 0.4676 0.0460 1.0000 Uiso . . . . . . . H132 H 0.2170 0.4841 0.3741 0.0460 1.0000 Uiso . . . . . . . H141 H 0.1347 0.3592 0.4639 0.0465 1.0000 Uiso . . . . . . . H142 H 0.2466 0.2947 0.4583 0.0465 1.0000 Uiso . . . . . . . H151 H 0.2756 0.2166 0.3100 0.0458 1.0000 Uiso . . . . . . . H152 H 0.1858 0.2326 0.2147 0.0458 1.0000 Uiso . . . . . . . H161 H 0.2542 0.4010 0.2144 0.0453 1.0000 Uiso . . . . . . . H162 H 0.3660 0.3342 0.2186 0.0453 1.0000 Uiso . . . . . . . H171 H 0.3790 0.6044 0.3993 0.0327 1.0000 Uiso . . . . . . . H181 H 1.6434 0.6999 0.1058 0.0511 1.0000 Uiso . . . . . . . H191 H 1.5981 0.5813 -0.0278 0.0535 1.0000 Uiso . . . . . . . H192 H 1.4615 0.6072 -0.0440 0.0535 1.0000 Uiso . . . . . . . H201 H 1.6591 0.7605 -0.0512 0.0466 1.0000 Uiso . . . . . . . H202 H 1.5224 0.7864 -0.0675 0.0466 1.0000 Uiso . . . . . . . H221 H 1.3756 0.6075 0.0970 0.0437 1.0000 Uiso . . . . . . . H271 H 1.3131 0.9951 0.2560 0.0468 1.0000 Uiso . . . . . . . H301 H 1.7977 1.0185 0.1081 0.0414 1.0000 Uiso . . . . . . . H302 H 1.6936 1.0326 0.0215 0.0414 1.0000 Uiso . . . . . . . H311 H 1.8620 1.1433 0.0071 0.0457 1.0000 Uiso . . . . . . . H312 H 1.7502 1.2054 0.0201 0.0457 1.0000 Uiso . . . . . . . H321 H 1.8410 1.2698 0.2655 0.0496 1.0000 Uiso . . . . . . . H322 H 1.7378 1.2845 0.1784 0.0496 1.0000 Uiso . . . . . . . H331 H 1.7835 1.0991 0.2674 0.0469 1.0000 Uiso . . . . . . . H332 H 1.6707 1.1614 0.2769 0.0469 1.0000 Uiso . . . . . . . H341 H 1.6308 0.8925 0.0982 0.0391 1.0000 Uiso . . . . . . . H3111 H 0.0862 0.2397 0.3450 0.0464 1.0000 Uiso . . . . . . . H6111 H 1.9167 1.2705 0.1207 0.0484 1.0000 Uiso . . . . . . . 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 N1 0.0338(11) 0.0437(11) 0.0233(11) 0.0072(11) 0.0103(11) -0.0127(11) N2 0.0247(14) 0.0553(14) 0.0336(14) 0.0091(14) 0.0092(14) -0.0174(14) N3 0.0250(14) 0.0559(14) 0.0350(14) 0.0093(14) 0.0099(14) -0.0177(14) C1 0.037(2) 0.059(2) 0.031(2) 0.001(2) 0.015(2) -0.003(2) C2 0.028(2) 0.049(2) 0.052(2) -0.001(2) 0.018(2) -0.016(2) C3 0.041(2) 0.056(2) 0.031(2) 0.014(2) -0.003(2) -0.007(2) C4 0.0214(11) 0.0428(11) 0.0148(11) 0.0100(11) 0.0024(11) -0.0109(11) C5 0.0395(11) 0.0432(11) 0.0207(11) 0.0096(11) 0.0094(11) -0.0152(11) C6 0.0326(11) 0.0449(11) 0.0179(11) 0.0133(11) 0.0043(11) -0.0165(11) C7 0.0351(18) 0.0500(18) 0.0501(18) 0.0043(18) 0.0140(18) -0.0288(18) C8 0.0237(11) 0.0456(11) 0.0249(11) 0.0132(11) 0.0051(11) -0.0137(11) C9 0.0187(11) 0.0429(11) 0.0184(11) 0.0122(11) 0.0021(11) -0.0106(11) C10 0.0192(11) 0.0437(11) 0.0306(11) 0.0100(11) 0.0078(11) -0.0100(11) C11 0.0186(11) 0.0430(11) 0.0247(11) 0.0086(11) 0.0053(11) -0.0104(11) C12 0.0166(11) 0.0445(11) 0.0149(11) 0.0078(11) 0.0010(11) -0.0117(11) C13 0.0252(14) 0.0558(14) 0.0339(14) 0.0092(14) 0.0097(14) -0.0174(14) C14 0.0255(14) 0.0561(14) 0.0346(14) 0.0094(14) 0.0100(14) -0.0176(14) C15 0.0245(14) 0.0554(14) 0.0346(14) 0.0092(14) 0.0094(14) -0.0177(14) C16 0.0241(14) 0.0551(14) 0.0339(14) 0.0090(14) 0.0091(14) -0.0175(14) C17 0.0195(11) 0.0451(11) 0.0173(11) 0.0071(11) 0.0037(11) -0.0112(11) O1 0.0462(18) 0.0580(18) 0.0646(18) -0.0079(18) 0.0212(18) -0.0381(18) O2 0.0536(18) 0.0535(18) 0.0665(18) 0.0084(18) 0.0316(18) -0.0277(18) O3 0.023(7) 0.064(8) 0.037(7) 0.017(6) 0.006(5) -0.003(6) F1 0.039(6) 0.041(6) 0.042(6) 0.010(5) 0.017(5) -0.012(5) N4 0.0212(12) 0.0614(12) 0.0223(12) 0.0026(12) 0.0000(12) -0.0147(12) N5 0.0242(14) 0.0540(14) 0.0336(14) 0.0098(14) 0.0122(14) -0.0145(14) N6 0.0301(14) 0.0567(14) 0.0341(14) 0.0142(14) 0.0128(14) -0.0190(14) C18 0.037(2) 0.059(2) 0.032(2) 0.000(2) 0.014(2) -0.005(2) C19 0.029(2) 0.051(2) 0.054(2) -0.003(2) 0.017(2) -0.017(2) C20 0.037(2) 0.052(2) 0.027(2) 0.013(2) -0.005(2) -0.008(2) C21 0.0215(12) 0.0601(12) 0.0189(12) 0.0059(12) 0.0040(12) -0.0137(12) C22 0.0212(12) 0.0630(12) 0.0252(12) 0.0041(12) -0.0037(12) -0.0166(12) C23 0.0211(12) 0.0657(12) 0.0225(12) 0.0099(12) -0.0024(12) -0.0173(12) C24 0.0231(17) 0.0669(17) 0.0259(17) 0.0169(17) 0.0033(17) -0.0176(17) C25 0.0261(12) 0.0757(12) 0.0167(12) 0.0125(12) 0.0083(12) -0.0149(12) C26 0.0238(12) 0.0626(12) 0.0204(12) 0.0074(12) 0.0073(12) -0.0143(12) C27 0.0276(12) 0.0634(12) 0.0261(12) 0.0063(12) 0.0129(12) -0.0128(12) C28 0.0268(12) 0.0595(12) 0.0283(12) 0.0068(12) 0.0117(12) -0.0113(12) C29 0.0223(12) 0.0572(12) 0.0224(12) 0.0094(12) 0.0068(12) -0.0109(12) C30 0.0164(14) 0.0553(14) 0.0318(14) 0.0113(14) 0.0064(14) -0.0098(14) C31 0.0205(14) 0.0605(14) 0.0333(14) 0.0147(14) 0.0100(14) -0.0116(14) C32 0.0323(14) 0.0528(14) 0.0389(14) 0.0103(14) 0.0145(14) -0.0178(14) C33 0.0271(14) 0.0553(14) 0.0349(14) 0.0087(14) 0.0136(14) -0.0192(14) C34 0.0206(12) 0.0586(12) 0.0185(12) 0.0074(12) 0.0046(12) -0.0118(12) O4 0.0247(17) 0.0718(17) 0.0327(17) 0.0097(17) 0.0051(17) -0.0223(17) O5 0.0200(17) 0.0719(17) 0.0356(17) 0.0134(17) 0.0046(17) -0.0174(17) O6 0.058(9) 0.068(9) 0.043(8) 0.021(6) 0.027(6) -0.005(7) F2 0.028(6) 0.055(7) 0.046(6) -0.001(5) 0.015(5) -0.016(5) O100 0.031(7) 0.060(9) 0.068(9) 0.018(7) 0.006(6) -0.014(6) O102 0.057(9) 0.085(10) 0.043(8) 0.010(7) 0.013(6) -0.021(7) O104 0.060(10) 0.170(17) 0.117(13) -0.083(13) 0.009(9) 0.010(10) O107 0.084(11) 0.113(12) 0.057(9) 0.050(8) -0.021(8) -0.049(9) O108 0.138(15) 0.120(13) 0.068(11) 0.028(9) 0.010(10) -0.073(12) O109 0.046(8) 0.064(9) 0.044(8) 0.002(6) 0.018(6) -0.021(7) Na1 0.021(4) 0.089(6) 0.043(4) 0.016(4) 0.010(3) -0.026(4) Na2 0.021(4) 0.063(5) 0.040(4) 0.014(3) 0.007(3) -0.024(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2477(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C1 . 1.463(9) yes N1 . C4 . 1.400(8) yes N1 . C5 . 1.357(9) yes N2 . C12 . 1.397(8) yes N2 . C13 . 1.486(9) yes N2 . C16 . 1.498(10) yes N3 . C14 . 1.471(10) yes N3 . C15 . 1.480(10) yes N3 . H3111 . 0.880 no C1 . C3 . 1.472(7) yes C1 . C2 . 1.487(7) yes C1 . H11 . 0.950 no C2 . C3 . 1.501(8) yes C2 . H21 . 0.950 no C2 . H22 . 0.950 no C3 . H31 . 0.950 no C3 . H32 . 0.950 no C4 . C9 . 1.400(8) yes C4 . C17 . 1.403(9) yes C5 . C6 . 1.381(9) yes C5 . H51 . 0.950 no C6 . C7 . 1.516(8) yes C6 . C8 . 1.434(8) yes C7 . O1 . 1.267(9) yes C7 . O2 . 1.258(9) yes C8 . C9 . 1.469(8) yes C8 . O3 . 1.255(9) yes C9 . C10 . 1.404(9) yes C10 . C11 . 1.370(9) yes C10 . H101 . 0.950 no C11 . C12 . 1.420(8) yes C11 . F1 . 1.354(8) yes C12 . C17 . 1.382(9) yes C13 . C14 . 1.504(10) yes C13 . H131 . 0.950 no C13 . H132 . 0.950 no C14 . H141 . 0.950 no C14 . H142 . 0.950 no C15 . C16 . 1.512(10) yes C15 . H151 . 0.950 no C15 . H152 . 0.951 no C16 . H161 . 0.950 no C16 . H162 . 0.950 no C17 . H171 . 0.950 no O2 . Na1 . 2.405(14) yes O3 . Na1 . 2.338(10) yes O3 . Na2 . 2.529(11) yes N4 . C18 . 1.446(11) yes N4 . C21 . 1.413(10) yes N4 . C22 . 1.353(10) yes N5 . C29 . 1.426(9) yes N5 . C30 . 1.465(11) yes N5 . C33 . 1.470(12) yes N6 . C31 . 1.483(12) yes N6 . C32 . 1.500(12) yes N6 . H6111 . 0.880 no C18 . C20 . 1.477(9) yes C18 . C19 . 1.490(9) yes C18 . H181 . 0.950 no C19 . C20 . 1.505(10) yes C19 . H191 . 0.950 no C19 . H192 . 0.950 no C20 . H201 . 0.950 no C20 . H202 . 0.950 no C21 . C26 . 1.366(9) yes C21 . C34 . 1.421(10) yes C22 . C23 . 1.376(11) yes C22 . H221 . 0.950 no C23 . C24 . 1.543(9) yes C23 . C25 . 1.430(10) yes C24 . O4 . 1.278(11) yes C24 . O5 . 1.249(10) yes C25 . C26 . 1.484(9) yes C25 . O6 . 1.252(11) yes C26 . C27 . 1.407(11) yes C27 . C28 . 1.377(10) yes C27 . H271 . 0.950 no C28 . C29 . 1.379(9) yes C28 . F2 . 1.373(10) yes C29 . C34 . 1.389(11) yes C30 . C31 . 1.527(12) yes C30 . H301 . 0.950 no C30 . H302 . 0.950 no C31 . H311 . 0.950 no C31 . H312 . 0.950 no C32 . C33 . 1.511(12) yes C32 . H321 . 0.950 no C32 . H322 . 0.950 no C33 . H331 . 0.950 no C33 . H332 . 0.950 no C34 . H341 . 0.950 no O5 . Na1 . 2.268(12) yes O5 . Na2 . 2.374(11) yes O6 . Na1 . 2.236(10) yes O100 . Na2 . 2.301(13) yes O101 . Na2 . 2.346(12) yes O102 . Na2 . 2.339(12) yes O1050 . Na1 . 2.40(2) yes O1051 . Na1 . 2.28(2) yes Na1 . Na2 . 3.192(9) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . N1 . C4 . 121.1(2) yes C1 . N1 . C5 . 120.0(2) yes C4 . N1 . C5 . 118.9(2) yes C12 . N2 . C13 . 116.0(3) yes C12 . N2 . C16 . 116.0(3) yes C13 . N2 . C16 . 111.0(3) yes C14 . N3 . C15 . 108.2(3) yes C14 . N3 . H3111 . 109.8 no C15 . N3 . H3111 . 109.8 no N1 . C1 . C3 . 118.3(3) yes N1 . C1 . C2 . 120.1(3) yes C3 . C1 . C2 . 61.0(2) yes N1 . C1 . H11 . 115.6 no C3 . C1 . H11 . 115.5 no C2 . C1 . H11 . 115.5 no C1 . C3 . C2 . 60.0(2) yes C1 . C3 . H31 . 120.0 no C2 . C3 . H31 . 120.0 no C1 . C3 . H32 . 120.0 no C2 . C3 . H32 . 120.0 no H31 . C3 . H32 . 109.5 no C3 . C2 . C1 . 59.0(2) yes C3 . C2 . H21 . 120.1 no C1 . C2 . H21 . 120.2 no C3 . C2 . H22 . 120.2 no C1 . C2 . H22 . 120.2 no H21 . C2 . H22 . 109.5 no N1 . C4 . C9 . 119.3(2) yes N1 . C4 . C17 . 119.6(2) yes C9 . C4 . C17 . 121.0(2) yes N1 . C5 . C6 . 124.9(2) yes N1 . C5 . H51 . 117.5 no C6 . C5 . H51 . 117.6 no C5 . C6 . C7 . 116.6(2) yes C5 . C6 . C8 . 119.6(2) yes C7 . C6 . C8 . 123.8(2) yes C6 . C7 . O1 . 115.9(2) yes C6 . C7 . O2 . 119.1(2) yes O1 . C7 . O2 . 125.0(2) yes C6 . C8 . C9 . 114.9(2) yes C6 . C8 . O3 . 125.3(2) yes C9 . C8 . O3 . 119.7(2) yes C8 . C9 . C4 . 122.3(2) yes C8 . C9 . C10 . 119.0(2) yes C4 . C9 . C10 . 118.7(2) yes C9 . C10 . C11 . 119.3(2) yes C9 . C10 . H101 . 120.3 no C11 . C10 . H101 . 120.3 no C10 . C11 . C12 . 123.0(2) yes C10 . C11 . F1 . 117.4(2) yes C12 . C11 . F1 . 119.6(2) yes C11 . C12 . N2 . 119.7(2) yes C11 . C12 . C17 . 117.2(2) yes N2 . C12 . C17 . 123.1(2) yes N2 . C13 . C14 . 109.6(3) yes N2 . C13 . H131 . 109.4 no C14 . C13 . H131 . 109.5 no N2 . C13 . H132 . 109.5 no C14 . C13 . H132 . 109.4 no H131 . C13 . H132 . 109.5 no C13 . C14 . N3 . 111.3(3) yes C13 . C14 . H141 . 109.0 no N3 . C14 . H141 . 109.0 no C13 . C14 . H142 . 109.0 no N3 . C14 . H142 . 109.0 no H141 . C14 . H142 . 109.4 no N3 . C15 . C16 . 110.6(3) yes N3 . C15 . H151 . 109.2 no C16 . C15 . H151 . 109.2 no N3 . C15 . H152 . 109.2 no C16 . C15 . H152 . 109.2 no H151 . C15 . H152 . 109.5 no C15 . C16 . N2 . 110.8(3) yes C15 . C16 . H161 . 109.2 no N2 . C16 . H161 . 109.1 no C15 . C16 . H162 . 109.1 no N2 . C16 . H162 . 109.2 no H161 . C16 . H162 . 109.4 no C4 . C17 . C12 . 120.7(2) yes C4 . C17 . H171 . 119.7 no C12 . C17 . H171 . 119.6 no C7 . O2 . Na1 . 115.2(9) yes C8 . O3 . Na1 . 125.7(6) yes C8 . O3 . Na2 . 142.8(9) yes Na1 . O3 . Na2 . 81.9(3) yes C18 . N4 . C21 . 121.1(2) yes C18 . N4 . C22 . 120.0(2) yes C21 . N4 . C22 . 118.9(2) yes C29 . N5 . C30 . 116.7(3) yes C29 . N5 . C33 . 116.3(3) yes C30 . N5 . C33 . 111.1(3) yes C31 . N6 . C32 . 108.4(3) yes C31 . N6 . H6111 . 109.7 no C32 . N6 . H6111 . 109.7 no N4 . C18 . C20 . 118.3(3) yes N4 . C18 . C19 . 120.1(3) yes C20 . C18 . C19 . 60.9(2) yes N4 . C18 . H181 . 115.5 no C20 . C18 . H181 . 115.5 no C19 . C18 . H181 . 115.5 no C18 . C20 . C19 . 60.0(2) yes C18 . C20 . H201 . 120.0 no C19 . C20 . H201 . 120.0 no C18 . C20 . H202 . 120.0 no C19 . C20 . H202 . 120.0 no H201 . C20 . H202 . 109.5 no C20 . C19 . C18 . 59.1(2) yes C20 . C19 . H191 . 120.2 no C18 . C19 . H191 . 120.1 no C20 . C19 . H192 . 120.2 no C18 . C19 . H192 . 120.1 no H191 . C19 . H192 . 109.5 no N4 . C21 . C26 . 119.4(2) yes N4 . C21 . C34 . 119.8(2) yes C26 . C21 . C34 . 120.8(2) yes N4 . C22 . C23 . 124.8(2) yes N4 . C22 . H221 . 117.6 no C23 . C22 . H221 . 117.6 no C22 . C23 . C24 . 116.5(2) yes C22 . C23 . C25 . 119.4(2) yes C24 . C23 . C25 . 123.8(2) yes C23 . C24 . O4 . 115.9(2) yes C23 . C24 . O5 . 119.1(2) yes O4 . C24 . O5 . 125.0(2) yes C23 . C25 . C26 . 115.0(2) yes C23 . C25 . O6 . 125.5(2) yes C26 . C25 . O6 . 119.5(2) yes C25 . C26 . C21 . 122.4(2) yes C25 . C26 . C27 . 118.9(2) yes C21 . C26 . C27 . 118.7(2) yes C26 . C27 . C28 . 119.6(2) yes C26 . C27 . H271 . 120.2 no C28 . C27 . H271 . 120.2 no C27 . C28 . C29 . 123.1(2) yes C27 . C28 . F2 . 117.4(2) yes C29 . C28 . F2 . 119.5(2) yes N5 . C29 . C28 . 119.2(2) yes N5 . C29 . C34 . 123.4(2) yes C28 . C29 . C34 . 117.3(2) yes N5 . C30 . C31 . 109.3(3) yes N5 . C30 . H301 . 109.5 no C31 . C30 . H301 . 109.5 no N5 . C30 . H302 . 109.5 no C31 . C30 . H302 . 109.6 no H301 . C30 . H302 . 109.4 no C30 . C31 . N6 . 111.5(3) yes C30 . C31 . H311 . 109.0 no N6 . C31 . H311 . 109.0 no C30 . C31 . H312 . 109.0 no N6 . C31 . H312 . 109.0 no H311 . C31 . H312 . 109.5 no N6 . C32 . C33 . 110.8(3) yes N6 . C32 . H321 . 109.2 no C33 . C32 . H321 . 109.1 no N6 . C32 . H322 . 109.1 no C33 . C32 . H322 . 109.1 no H321 . C32 . H322 . 109.5 no C32 . C33 . N5 . 110.8(3) yes C32 . C33 . H331 . 109.2 no N5 . C33 . H331 . 109.2 no C32 . C33 . H332 . 109.1 no N5 . C33 . H332 . 109.1 no H331 . C33 . H332 . 109.5 no C21 . C34 . C29 . 120.5(2) yes C21 . C34 . H341 . 119.8 no C29 . C34 . H341 . 119.8 no C24 . O5 . Na1 . 137.3(4) yes C24 . O5 . Na2 . 109.7(9) yes Na1 . O5 . Na2 . 86.8(4) yes C25 . O6 . Na1 . 133.8(5) yes O3 . Na1 . O1051 . 109.3(6) yes O3 . Na1 . O5 . 87.6(4) yes O1051 . Na1 . O5 . 121.4(8) yes O3 . Na1 . O6 . 144.1(5) yes O1051 . Na1 . O6 . 106.3(6) yes O5 . Na1 . O6 . 77.8(4) yes O3 . Na1 . O1050 . 105.6(6) yes O1051 . Na1 . O1050 . 18.2(7) yes O5 . Na1 . O1050 . 103.9(7) yes O6 . Na1 . O1050 . 109.6(6) yes O3 . Na1 . O2 . 73.8(4) yes O1051 . Na1 . O2 . 99.0(7) yes O5 . Na1 . O2 . 139.4(5) yes O6 . Na1 . O2 . 96.4(4) yes O1050 . Na1 . O2 . 115.7(7) yes O3 . Na1 . Na2 . 51.7(3) yes O1051 . Na1 . Na2 . 152.6(7) yes O5 . Na1 . Na2 . 48.0(3) yes O6 . Na1 . Na2 . 96.1(3) yes O1050 . Na1 . Na2 . 137.2(7) yes O2 . Na1 . Na2 . 93.9(3) yes O100 . Na2 . O102 . 91.0(5) yes O100 . Na2 . O101 . 139.5(5) yes O102 . Na2 . O101 . 93.1(4) yes O100 . Na2 . O5 . 108.8(4) yes O102 . Na2 . O5 . 105.4(4) yes O101 . Na2 . O5 . 108.9(4) yes O100 . Na2 . Na1 . 71.9(3) yes O102 . Na2 . Na1 . 130.9(4) yes O101 . Na2 . Na1 . 129.9(4) yes O5 . Na2 . Na1 . 45.2(3) yes O100 . Na2 . O3 . 75.3(4) yes O102 . Na2 . O3 . 166.2(5) yes O101 . Na2 . O3 . 96.4(4) yes O5 . Na2 . O3 . 81.1(4) yes Na1 . Na2 . O3 . 46.5(2) yes #===END data_6 _database_code_depnum_ccdc_archive 'CCDC 714349' #Cf Na salt recovered to ambient pressure and #remeasured a second time at 100 K _cell_length_a 9.624(3) _cell_length_b 9.493(3) _cell_length_c 11.471(4) _cell_angle_alpha 89.643(6) _cell_angle_beta 103.304(6) _cell_angle_gamma 88.861(6) _cell_volume 1019.6(6) _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 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Na 0.0362 0.0249 4.7626 3.2850 3.1736 8.8422 1.2674 0.3136 1.1128 129.4240 0.6760 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C17 H17 F1 N3 Na1 O8 # Dc = 1.41 Fooo = 466.00 Mu = 1.36 M = 433.33 # Found Formula = C17 H26 F1 N3 Na1 O8 # Dc = 1.44 FOOO = 466.00 Mu = 1.37 M = 442.40 _chemical_formula_sum 'C17 H27 F1 N3 Na1 O8' _chemical_formula_moiety 'C17 H17 F N3 O3, 5(H2 O), NA' _chemical_compound_source ; recovery of 4 to ambient pressure, second 100 K data collection ; _chemical_formula_weight 443.40 _cell_measurement_reflns_used 1718 _cell_measurement_theta_min 2 _cell_measurement_theta_max 21 _cell_measurement_temperature 100 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_max 0.15 _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.137 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'based on symmetry-related measuraments' # SADABS (Siemens, 1996) # The following data are from Sadabs: _exptl_absorpt_correction_T_min 0.83 _exptl_absorpt_correction_T_max 0.99 # Sheldrick geometric approximatio 0.99 0.99 _diffrn_measurement_device 'Bruker Apex2' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'Starting from fract. coordinates of 4' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003), PLATON, XCIF, ENCIFER' _computing_molecular_graphics MERCURY _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 100 _diffrn_reflns_number 7265 _reflns_number_total 2130 _diffrn_reflns_av_R_equivalents 0.051 # Number of reflections with Friedels Law is 2130 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2140 _diffrn_reflns_theta_min 1.824 _diffrn_reflns_theta_max 20.831 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 20.206 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min -9 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 11 _oxford_diffrn_Wilson_B_factor 1.10 _oxford_diffrn_Wilson_scale 3.21 _atom_sites_solution_primary ; 'Starting from fract. coordinates of 4' ; # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom+difmap _refine_diff_density_min -0.45 _refine_diff_density_max 0.52 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 2119 _refine_ls_number_restraints 66 _refine_ls_number_parameters 270 _oxford_refine_ls_R_factor_ref 0.0798 _refine_ls_wR_factor_ref 0.1360 _refine_ls_goodness_of_fit_ref 1.0012 _refine_ls_shift/su_max 0.000142 # The values computed from all data _oxford_reflns_number_all 2119 _refine_ls_R_factor_all 0.0798 _refine_ls_wR_factor_all 0.1360 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1572 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_gt 0.1242 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 4.81P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_special_details ; The Following ALERTS were generated by PLATON checkcif<<< 023_ALERT_3_A Resolution (too) Low [sin(th)/Lambda < 0.6]..... 20.83 Deg. 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 20.21 Deg. 340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7 These alerts indicate that the structure quality is not ideal. However, this is the best structure we could obtain from the data collected on this small, weakly diffracting crystal recovered at ambient pressure. Data were collected at low temperature, with high counting time and with a laboratory X-ray source. The low crystal quality was also reflected in the broad and at times split reflection profiles. The data were cut to 1.0 A for integration as no significan scattering was observed for this small crystal at higher resolution. The dataset is complete to 1.0 A as shown below: #=============================================================================== Resolution & Completeness Statistics (Cumulative) #=============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------- 20.82 0.500 0.993 2144 2128 16 20.83 0.500 0.991 2149 2130 19 088_ALERT_3_B Poor Data / Parameter Ratio .................... 7.85 The use of restraints bond distances and angles for a total of 332, increases the data to parameter ratio to 8.1. All bond lengths and ADPs are well behaved. 417_ALERT_2_B Short Inter D-H..H-D H1001 .. H1031 .. 1.91 Ang. 417_ALERT_2_B Short Inter D-H..H-D H1011 .. H1041 .. 2.09 Ang. 420_ALERT_2_B D-H Without Acceptor O102 - H1021 ... ? 420_ALERT_2_C D-H Without Acceptor N3 - H312 ... ? The first short contact arises because of disorder, the second might arise because of misplaced H-atoms. Though the positions of water H-atoms were inferred from the data and the H-bonding pattern is plausible and self consistent, the data quality does not allow definitive conclusions to be drawn. According to the proposed pattern, O102-H1021 forms a long H-bond to N3. It is not quite so rare for N-H not to be involved in H-bonding. We also cannot rule the presence of H disorder. 041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? 042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? 045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio The formulae given and derived properties are correct. Two water H-atoms are missing in the model, attached to O1032, but these were included for the calculation of formulae, molecular weight, density, mu and F000. 061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.85 Sadabs corrects for all systematic errors that lead to disparities in the intensities of equivalent data. It is possible that the larger than expected range of transmission is accounted for by crystal decay or absorption by the mounting fibre. 155_ALERT_4_C The Triclinic Unitcell is NOT Reduced .......... ? 156_ALERT_4_C Axial System Input Cell not Standard ........... ? The cell was chose to facilitate comparision with the known structure of Cf hexahydrate, CSD ref. code COVPIN and the other structures presented in this work. 302_ALERT_4_C Anion/Solvent Disorder ......................... 33.00 Perc. 313_ALERT_2_C Oxygen with three covalent bonds (rare) ........ O1031 One water O-atom was found to be disordered over two sites. O1031 does not have three covalent bonds. This alert arises because the disordered counterpart, O1032, has been counted in addition to two H-atoms atached to O1031. 720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 12 154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 600 Deg. 860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 66 Noted, no action taken. 790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 H2 O Noted, no action taken. The centre of gravity of the main Cf moiety is within the unit cell. Water O-atoms were transformed to give a clear picture of the coordination environment of the Cf moiety. ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens C1 C 0.2285(5) 0.3691(5) 0.4612(4) 0.0215 1.0000 Uani D . . . . . . C2 C 0.3851(5) 0.3526(6) 0.4728(5) 0.0231 1.0000 Uani D . . . . . . C3 C 0.2882(5) 0.2324(5) 0.4334(5) 0.0208 1.0000 Uani D . . . . . . C4 C 0.0460(5) 0.3132(5) 0.5752(4) 0.0184 1.0000 Uani D . . . . . . C5 C 0.2396(5) 0.4594(5) 0.6614(5) 0.0192 1.0000 Uani D . . . . . . C6 C 0.1963(5) 0.4783(5) 0.7670(4) 0.0181 1.0000 Uani D . . . . . . C7 C 0.2845(5) 0.5734(5) 0.8569(4) 0.0201 1.0000 Uani D . . . . . . C8 C 0.0717(5) 0.4067(5) 0.7839(4) 0.0173 1.0000 Uani D . . . . . . C9 C -0.0035(5) 0.3251(5) 0.6802(4) 0.0175 1.0000 Uani D . . . . . . C10 C -0.1265(6) 0.2506(6) 0.6878(5) 0.0210 1.0000 Uani D . . . . . . C11 C -0.1969(5) 0.1762(5) 0.5928(5) 0.0212 1.0000 Uani D . . . . . . C12 C -0.1529(5) 0.1657(5) 0.4846(4) 0.0201 1.0000 Uani D . . . . . . C13 C -0.1646(6) 0.0548(6) 0.2908(5) 0.0255 1.0000 Uani D . . . . . . C14 C -0.2493(6) -0.0568(6) 0.2090(5) 0.0290 1.0000 Uani D . . . . . . C15 C -0.4651(5) 0.0168(6) 0.2656(5) 0.0250 1.0000 Uani D . . . . . . C16 C -0.3843(6) 0.1288(6) 0.3462(5) 0.0289 1.0000 Uani D . . . . . . C17 C -0.0297(5) 0.2365(5) 0.4779(5) 0.0204 1.0000 Uani D . . . . . . O1 O 0.4107(4) 0.5955(4) 0.8488(3) 0.0273 1.0000 Uani D . . . . . . O2 O 0.2260(4) 0.6307(4) 0.9331(3) 0.0251 1.0000 Uani D . . . . . . O3 O 0.0260(4) 0.4108(4) 0.8776(3) 0.0255 1.0000 Uani D . . . . . . N1 N 0.1721(4) 0.3804(4) 0.5688(4) 0.0170 1.0000 Uani D . . . . . . N2 N -0.2314(4) 0.0830(4) 0.3910(4) 0.0208 1.0000 Uani D . . . . . . N3 N -0.4018(5) -0.0189(5) 0.1637(4) 0.0265 1.0000 Uani D . . . . . . F1 F -0.3115(3) 0.1004(3) 0.6058(3) 0.0296 1.0000 Uani D . . . . . . Na1 Na 0.1723(2) 0.4563(2) 1.07331(18) 0.0270 1.0000 Uani . . . . . . . O100 O 0.0613(4) 0.2838(4) 1.1679(3) 0.0326 1.0000 Uani . . . . . . . O101 O 0.3701(4) 0.5497(4) 1.2209(3) 0.0275 1.0000 Uani . . . . . . . O102 O 0.3483(4) 0.2866(4) 1.0248(3) 0.0325 1.0000 Uani . . . . . . . O1031 O 0.1730(8) 0.0607(8) 1.0772(6) 0.0247(19) 0.5000 Uiso . . . 1 1 . . O1032 O 0.0911(9) -0.0004(9) 1.0804(8) 0.043(2) 0.5000 Uiso . . . 1 2 . . O104 O -0.3425(4) 0.1816(4) -0.0976(4) 0.0327 1.0000 Uani . . . . . . . H11 H 0.1785 0.4229 0.3940 0.0255 1.0000 Uiso . . . . . . . H21 H 0.4483 0.3507 0.5499 0.0274 1.0000 Uiso . . . . . . . H22 H 0.4294 0.3984 0.4175 0.0274 1.0000 Uiso . . . . . . . H31 H 0.2899 0.1537 0.4853 0.0249 1.0000 Uiso . . . . . . . H32 H 0.2709 0.2014 0.3529 0.0249 1.0000 Uiso . . . . . . . H51 H 0.3236 0.5056 0.6531 0.0224 1.0000 Uiso . . . . . . . H101 H -0.1600 0.2526 0.7596 0.0261 1.0000 Uiso . . . . . . . H131 H -0.0693 0.0212 0.3210 0.0300 1.0000 Uiso . . . . . . . H132 H -0.1637 0.1394 0.2462 0.0300 1.0000 Uiso . . . . . . . H141 H -0.2428 -0.1428 0.2529 0.0351 1.0000 Uiso . . . . . . . H142 H -0.2075 -0.0696 0.1423 0.0351 1.0000 Uiso . . . . . . . H151 H -0.5603 0.0503 0.2350 0.0292 1.0000 Uiso . . . . . . . H152 H -0.4659 -0.0661 0.3121 0.0292 1.0000 Uiso . . . . . . . H161 H -0.4267 0.1429 0.4123 0.0355 1.0000 Uiso . . . . . . . H162 H -0.3887 0.2145 0.3021 0.0355 1.0000 Uiso . . . . . . . H171 H 0.0036 0.2327 0.4062 0.0253 1.0000 Uiso . . . . . . . H312 H -0.4101 0.0542 0.1148 0.0305 1.0000 Uiso . . . . . . . H1001 H 0.0920 0.2079 1.1428 0.0497 1.0000 Uiso . . . . . . . H1002 H -0.0170 0.3158 1.1310 0.0493 1.0000 Uiso . . . . . . . H1011 H 0.3844 0.6279 1.1915 0.0434 1.0000 Uiso . . . . . . . H1012 H 0.4366 0.5107 1.1962 0.0434 1.0000 Uiso . . . . . . . H1021 H 0.3671 0.2561 0.9620 0.0494 1.0000 Uiso . . . . . . . H1022 H 0.4264 0.3255 1.0496 0.0492 1.0000 Uiso . . . . . . . H1031 H 0.2299 0.1241 1.0676 0.0408 0.5000 Uiso . . . 1 1 . . H1032 H 0.1963 -0.0225 1.0737 0.0410 0.5000 Uiso . . . 1 1 . . H1041 H -0.3324 0.2382 -0.0418 0.0529 1.0000 Uiso . . . . . . . H1042 H -0.4185 0.1442 -0.0888 0.0529 1.0000 Uiso . . . . . . . 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 0.021(3) 0.026(3) 0.017(3) 0.001(3) 0.003(3) -0.002(3) C2 0.017(3) 0.032(4) 0.019(3) -0.001(3) 0.001(3) -0.002(3) C3 0.020(3) 0.026(3) 0.016(3) -0.004(3) 0.003(3) 0.000(3) C4 0.015(3) 0.015(3) 0.023(4) 0.000(3) -0.001(3) 0.002(3) C5 0.020(3) 0.017(3) 0.019(4) -0.004(3) 0.001(3) 0.001(3) C6 0.018(3) 0.022(3) 0.013(3) -0.003(3) 0.001(3) 0.004(3) C7 0.020(4) 0.024(3) 0.015(3) 0.003(3) 0.001(3) 0.008(3) C8 0.019(3) 0.023(3) 0.009(3) -0.004(3) 0.002(3) 0.011(3) C9 0.021(3) 0.016(3) 0.017(3) 0.000(3) 0.006(3) 0.008(3) C10 0.024(3) 0.021(3) 0.020(3) -0.003(3) 0.010(3) 0.005(3) C11 0.019(3) 0.016(3) 0.031(4) 0.002(3) 0.011(3) 0.000(3) C12 0.021(3) 0.015(3) 0.023(4) -0.002(3) 0.004(3) 0.004(3) C13 0.022(3) 0.024(3) 0.028(4) 0.000(3) 0.001(3) -0.003(3) C14 0.029(4) 0.026(4) 0.033(4) -0.005(3) 0.009(3) -0.001(3) C15 0.018(3) 0.028(3) 0.026(4) -0.004(3) 0.000(3) 0.001(3) C16 0.024(4) 0.025(3) 0.039(4) -0.004(3) 0.010(3) 0.000(3) C17 0.022(3) 0.020(3) 0.022(3) -0.001(3) 0.009(3) 0.002(3) O1 0.021(2) 0.035(2) 0.025(2) -0.0082(19) 0.0022(19) -0.0009(19) O2 0.025(2) 0.028(2) 0.022(2) -0.0062(19) 0.0049(19) 0.0039(18) O3 0.024(2) 0.034(2) 0.018(2) -0.0056(19) 0.0025(19) 0.0022(19) N1 0.017(3) 0.016(3) 0.018(3) -0.001(2) 0.005(2) 0.006(2) N2 0.017(3) 0.020(3) 0.026(3) -0.005(2) 0.007(2) 0.004(2) N3 0.023(3) 0.027(3) 0.027(3) 0.007(2) -0.001(2) 0.000(2) F1 0.0284(19) 0.0278(19) 0.036(2) -0.0059(15) 0.0134(16) -0.0070(16) Na1 0.0219(12) 0.0389(14) 0.0196(13) -0.0060(10) 0.0030(10) -0.0055(10) O100 0.020(2) 0.042(3) 0.033(2) 0.003(2) 0.0015(19) 0.0068(19) O101 0.026(2) 0.027(2) 0.030(2) -0.0014(18) 0.0063(19) 0.0025(18) O102 0.026(2) 0.039(3) 0.031(2) -0.014(2) 0.0016(19) -0.0048(19) O104 0.036(2) 0.028(2) 0.036(3) -0.009(2) 0.011(2) -0.002(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.5109(16) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C3 . 1.474(6) yes C1 . C2 . 1.487(7) yes C1 . N1 . 1.461(6) yes C1 . H11 . 0.950 no C2 . C3 . 1.494(7) yes C2 . H21 . 0.951 no C2 . H22 . 0.950 no C3 . H31 . 0.950 no C3 . H32 . 0.950 no C4 . C9 . 1.397(7) yes C4 . C17 . 1.402(7) yes C4 . N1 . 1.399(6) yes C5 . C6 . 1.380(7) yes C5 . N1 . 1.351(6) yes C5 . H51 . 0.950 no C6 . C7 . 1.496(7) yes C6 . C8 . 1.441(6) yes C7 . O1 . 1.261(6) yes C7 . O2 . 1.264(6) yes C8 . C9 . 1.475(6) yes C8 . O3 . 1.252(5) yes C9 . C10 . 1.411(7) yes C10 . C11 . 1.355(7) yes C10 . H101 . 0.950 no C11 . C12 . 1.404(7) yes C11 . F1 . 1.365(5) yes C12 . C17 . 1.391(7) yes C12 . N2 . 1.415(6) yes C13 . C14 . 1.538(7) yes C13 . N2 . 1.464(7) yes C13 . H131 . 0.950 no C13 . H132 . 0.950 no C14 . N3 . 1.476(7) yes C14 . H141 . 0.950 no C14 . H142 . 0.950 no C15 . C16 . 1.518(7) yes C15 . N3 . 1.474(7) yes C15 . H151 . 0.951 no C15 . H152 . 0.949 no C16 . N2 . 1.497(6) yes C16 . H161 . 0.950 no C16 . H162 . 0.950 no C17 . H171 . 0.950 no O2 . Na1 . 2.445(4) yes O3 . Na1 2_567 2.442(4) yes O3 . Na1 . 2.406(4) yes N3 . H312 . 0.881 no Na1 . O100 . 2.362(4) yes Na1 . O101 . 2.425(4) yes Na1 . O102 . 2.472(4) yes O100 . H1001 . 0.851 no O100 . H1002 . 0.826 no O101 . H1011 . 0.840 no O101 . H1012 . 0.838 no O102 . H1021 . 0.835 no O102 . H1022 . 0.834 no O1031 . H1031 . 0.845 no O1031 . H1032 . 0.820 no O104 . H1041 . 0.828 no O104 . H1042 . 0.846 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C3 . C1 . C2 . 60.6(3) yes C3 . C1 . N1 . 118.9(4) yes C2 . C1 . N1 . 119.8(4) yes C3 . C1 . H11 . 115.5 no C2 . C1 . H11 . 115.5 no N1 . C1 . H11 . 115.5 no C1 . C3 . C2 . 60.1(3) yes C1 . C3 . H31 . 120.0 no C2 . C3 . H31 . 120.0 no C1 . C3 . H32 . 120.0 no C2 . C3 . H32 . 120.0 no H31 . C3 . H32 . 109.5 no C3 . C2 . C1 . 59.3(3) yes C3 . C2 . H21 . 120.1 no C1 . C2 . H21 . 120.1 no C3 . C2 . H22 . 120.2 no C1 . C2 . H22 . 120.2 no H21 . C2 . H22 . 109.4 no C9 . C4 . C17 . 120.7(4) yes C9 . C4 . N1 . 118.7(4) yes C17 . C4 . N1 . 120.6(4) yes C6 . C5 . N1 . 125.2(4) yes C6 . C5 . H51 . 117.4 no N1 . C5 . H51 . 117.4 no C5 . C6 . C7 . 116.6(4) yes C5 . C6 . C8 . 118.9(4) yes C7 . C6 . C8 . 124.5(4) yes C6 . C7 . O1 . 117.8(4) yes C6 . C7 . O2 . 118.0(4) yes O1 . C7 . O2 . 124.1(4) yes C6 . C8 . C9 . 115.1(4) yes C6 . C8 . O3 . 124.7(4) yes C9 . C8 . O3 . 120.3(4) yes C8 . C9 . C4 . 122.4(4) yes C8 . C9 . C10 . 119.5(4) yes C4 . C9 . C10 . 118.0(4) yes C9 . C10 . C11 . 119.9(4) yes C9 . C10 . H101 . 120.0 no C11 . C10 . H101 . 120.1 no C10 . C11 . C12 . 123.5(4) yes C10 . C11 . F1 . 118.0(4) yes C12 . C11 . F1 . 118.3(4) yes C11 . C12 . C17 . 116.6(4) yes C11 . C12 . N2 . 119.6(4) yes C17 . C12 . N2 . 123.8(4) yes C14 . C13 . N2 . 109.8(4) yes C14 . C13 . H131 . 109.4 no N2 . C13 . H131 . 109.4 no C14 . C13 . H132 . 109.4 no N2 . C13 . H132 . 109.4 no H131 . C13 . H132 . 109.5 no C13 . C14 . N3 . 113.8(4) yes C13 . C14 . H141 . 108.4 no N3 . C14 . H141 . 108.3 no C13 . C14 . H142 . 108.4 no N3 . C14 . H142 . 108.4 no H141 . C14 . H142 . 109.5 no C16 . C15 . N3 . 113.4(4) yes C16 . C15 . H151 . 108.4 no N3 . C15 . H151 . 108.5 no C16 . C15 . H152 . 108.5 no N3 . C15 . H152 . 108.5 no H151 . C15 . H152 . 109.5 no C15 . C16 . N2 . 110.0(4) yes C15 . C16 . H161 . 109.4 no N2 . C16 . H161 . 109.3 no C15 . C16 . H162 . 109.4 no N2 . C16 . H162 . 109.3 no H161 . C16 . H162 . 109.5 no C4 . C17 . C12 . 121.1(4) yes C4 . C17 . H171 . 119.5 no C12 . C17 . H171 . 119.4 no C7 . O2 . Na1 . 111.2(3) yes Na1 2_567 O3 . C8 . 131.3(3) yes Na1 2_567 O3 . Na1 . 90.37(14) yes C8 . O3 . Na1 . 124.1(3) yes C1 . N1 . C4 . 120.4(4) yes C1 . N1 . C5 . 120.0(4) yes C4 . N1 . C5 . 119.6(4) yes C16 . N2 . C13 . 110.7(4) yes C16 . N2 . C12 . 114.7(4) yes C13 . N2 . C12 . 116.3(4) yes C14 . N3 . C15 . 109.3(4) yes C14 . N3 . H312 . 109.5 no C15 . N3 . H312 . 109.5 no O3 . Na1 . O3 2_567 89.63(15) yes O3 . Na1 . O2 . 71.75(13) yes O3 2_567 Na1 . O2 . 96.07(15) yes O3 . Na1 . O100 . 93.53(14) yes O3 2_567 Na1 . O100 . 77.61(14) yes O2 . Na1 . O100 . 164.18(15) yes O3 . Na1 . O101 . 157.51(15) yes O3 2_567 Na1 . O101 . 100.06(14) yes O2 . Na1 . O101 . 86.97(14) yes O100 . Na1 . O101 . 108.31(15) yes O3 . Na1 . O102 . 87.03(14) yes O3 2_567 Na1 . O102 . 170.35(15) yes O2 . Na1 . O102 . 91.49(15) yes O100 . Na1 . O102 . 93.55(15) yes O101 . Na1 . O102 . 86.30(14) yes Na1 . O100 . H1001 . 101.8 no Na1 . O100 . H1002 . 88.7 no H1001 . O100 . H1002 . 117.7 no Na1 . O101 . H1011 . 103.6 no Na1 . O101 . H1012 . 97.8 no H1011 . O101 . H1012 . 92.0 no Na1 . O102 . H1021 . 135.4 no Na1 . O102 . H1022 . 103.7 no H1021 . O102 . H1022 . 95.6 no H1031 . O1031 . H1032 . 119.7 no H1041 . O104 . H1042 . 98.3 no