# Electronic Supplementary Material (ESI) for Chemical Science. # This journal is © The Royal Society of Chemistry 2020 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 2002496' loop_ _audit_author_name _audit_author_address 'Gary Stephen Nichol' ;The University of Edinburgh United Kingdom ; _audit_update_record ; 2020-05-07 deposited with the CCDC. 2020-10-05 downloaded from the CCDC. ; # local name jg19012 _audit_creation_date 2020-05-04 _audit_creation_method ; Olex2 1.3-beta (compiled 2020.04.02 svn.r1fbe7b6f for OlexSys, GUI svn.r6076) ; _shelx_SHELXL_version_number 2018/3 loop_ _audit_author_email '' g.s.nichol@ed.ac.uk _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C51 H61 N2 Na O5, 2(C4 H8 O)' _chemical_formula_sum 'C59 H77 N2 Na O7' _chemical_formula_weight 949.21 _chemical_absolute_configuration ad _chemical_melting_point ? _chemical_oxdiff_formula 'C61 H79 N2 Na1 O5' _chemical_oxdiff_usercomment '@ 120 K ' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.1353 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _space_group_crystal_system tetragonal _space_group_IT_number 78 _space_group_name_H-M_alt 'P 43' _space_group_name_Hall 'P 4cw' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+3/4' 'y, -x, z+1/4' _cell_length_a 9.8142(4) _cell_length_b 9.8142(4) _cell_length_c 54.0271(12) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 5203.8(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 15205 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 74.8770 _cell_measurement_theta_min 4.4630 _shelx_estimated_absorpt_T_max ? _shelx_estimated_absorpt_T_min ? _exptl_absorpt_coefficient_mu 0.689 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.36699 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description plate _exptl_crystal_F_000 2048 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -2 -3 -27 0.0390 -6 1 14 0.0283 0 3 29 0.0523 6 0 -6 0.0147 -2 -6 8 0.0037 3 0 30 0.0521 2 6 -6 0.0323 _exptl_crystal_recrystallization_method 'The material was recrystallised from a mixture of THF and toluene by slow cooling' _exptl_crystal_size_max 0.122 _exptl_crystal_size_mid 0.062 _exptl_crystal_size_min 0.039 loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -2.2473 -3.3603 -27.1331 -0.2414 0.0328 0.9699 -5.7507 1.2211 13.5260 0.9780 -0.1279 0.1648 0.3456 3.4915 29.3031 0.5205 -0.0692 -0.8510 6.2870 -0.2378 -5.5189 -0.8909 0.1162 -0.4390 -1.7706 -5.9263 8.4151 -0.0224 -0.8982 0.4391 3.1298 0.3096 30.4946 -0.0130 -0.4640 -0.8857 1.9828 5.9450 -6.3365 0.0215 0.8662 -0.4992 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0622 _diffrn_reflns_av_unetI/netI 0.0721 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 64 _diffrn_reflns_limit_l_min -64 _diffrn_reflns_number 10795 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 68.239 _diffrn_reflns_theta_min 4.505 _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 120.0 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.1574 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.8095 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -75.00 34.00 1.00 25.00 -- -41.67 83.00-128.00 109 2 \w -12.00 75.00 1.00 25.00 -- 41.67 -83.00 111.00 87 3 \w 34.00 144.00 1.00 30.00 -- 111.00 -83.00 111.00 110 4 \w 100.00 178.00 1.00 30.00 -- 111.00 83.00-128.00 78 5 \w -68.00 28.00 1.00 25.00 -- -41.67 57.00 120.00 96 6 \w -112.00 -15.00 1.00 25.00 -- -41.67 -57.00 -30.00 97 7 \w -126.00 -37.00 1.00 25.00 -- -41.67 178.00 90.00 89 8 \w 10.00 42.00 1.00 25.00 -- 41.67 78.00 -72.37 32 9 \w 103.00 178.00 1.00 30.00 -- 111.00 77.00 -90.00 75 10 \w 40.00 135.00 1.00 30.00 -- 111.00 -45.00 90.00 95 11 \w 97.00 178.00 1.00 30.00 -- 111.00 125.00 60.00 81 12 \w 87.00 178.00 1.00 30.00 -- 111.00 30.00 60.00 91 13 \w 103.00 178.00 1.00 30.00 -- 111.00 77.00 0.00 75 14 \w 39.00 112.00 1.00 30.00 -- 111.00-125.00 -30.00 73 15 \w 39.00 112.00 1.00 30.00 -- 111.00-125.00 120.00 73 16 \w 97.00 178.00 1.00 30.00 -- 111.00 125.00 90.00 81 17 \w 39.00 112.00 1.00 30.00 -- 111.00-125.00-120.00 73 18 \w 39.00 112.00 1.00 30.00 -- 111.00-125.00-180.00 73 19 \w 39.00 112.00 1.00 30.00 -- 111.00-125.00 90.00 73 20 \w 39.00 112.00 1.00 30.00 -- 111.00-125.00 -60.00 73 21 \w 39.00 112.00 1.00 30.00 -- 111.00-125.00 0.00 73 22 \w 87.00 178.00 1.00 30.00 -- 111.00 45.00-180.00 91 23 \w 97.00 178.00 1.00 30.00 -- 111.00 125.00-180.00 81 24 \w 97.00 178.00 1.00 30.00 -- 111.00 125.00 120.00 81 25 \w -112.00 -15.00 1.00 25.00 -- -41.67 -57.00-120.00 97 26 \w -112.00 -15.00 1.00 25.00 -- -41.67 -57.00 150.00 97 27 \w -112.00 -15.00 1.00 25.00 -- -41.67 -57.00 60.00 97 28 \w -128.00 -39.00 1.00 25.00 -- -41.67-178.00-120.00 89 29 \w 10.00 42.00 1.00 25.00 -- 41.67 80.00 106.94 32 30 \w 83.00 167.00 1.00 30.00 -- 111.00 61.00 120.00 84 31 \w 83.00 178.00 1.00 30.00 -- 111.00 61.00 -30.00 95 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Rigaku Oxford Diffraction SuperNova' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.1287592000 _diffrn_orient_matrix_UB_12 0.0595515000 _diffrn_orient_matrix_UB_13 0.0121855000 _diffrn_orient_matrix_UB_21 0.0080028000 _diffrn_orient_matrix_UB_22 0.1245964000 _diffrn_orient_matrix_UB_23 -0.0173030000 _diffrn_orient_matrix_UB_31 -0.0894283000 _diffrn_orient_matrix_UB_32 -0.0745097000 _diffrn_orient_matrix_UB_33 -0.0191104000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _diffrn_special_details ? _reflns_Friedel_coverage 0.975 _reflns_Friedel_fraction_full 0.997 _reflns_Friedel_fraction_max 0.997 _reflns_number_gt 7788 _reflns_number_total 10795 _reflns_special_details ; _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. Completness statistics refer to single and composite reflections containing twin component 1 only. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)' _computing_molecular_graphics 'Olex2 1.3-beta (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3-beta (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _refine_diff_density_max 0.259 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.056 _refine_ls_abs_structure_details ; Classical Flack method preferred over Parsons because s.u. lower. ; _refine_ls_abs_structure_Flack -0.06(19) _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 626 _refine_ls_number_reflns 10795 _refine_ls_number_restraints 71 _refine_ls_R_factor_all 0.0928 _refine_ls_R_factor_gt 0.0690 _refine_ls_restrained_S_all 0.975 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1117P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1656 _refine_ls_wR_factor_ref 0.1760 _refine_special_details ;The O-bound H atoms were initially located from a difference Fourier map and controlled using the AFIX 147 restraint. The diffraction pattern was twinned. This was deconvoluted with CrysAlisPro. The measured data set is rather weak and was cut at a resolution of 0.83 A. #=============================================================================== The Following Improvement and Query ALERTS were generated - (Acta-Mode) <<< #=============================================================================== Format: alert-number_ALERT_alert-type_alert-level text340 _ALERT_3_B Low Bond Precision on C-C Bonds ............... 0.01288 Ang. Not significant - relatively poor and twinned data #=============================================================================== 220_ALERT_2_C Non-Solvent Resd 1 C Ueq(max)/Ueq(min) Range 3.4 Ratio 234_ALERT_4_C Large Hirshfeld Difference C40 --C41 . 0.17 Ang. 243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors of O6 Check 243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors of O7 Check 244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors of C52 Check 244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors of C56 Check 244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors of C57 Check 244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors of C59 Check All pertains to solvent THF906_ALERT_3_C Large K Value in the Analysis of Variance ...... 2.271 Check 918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) . 4 Check #===============================================================================,Twin ; _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.500(3) 0.500(3) 2. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All O(H) groups At 1.5 times of: All C(H,H,H) groups 3. Uiso/Uaniso restraints and constraints O7 \\sim C56 \\sim C57 \\sim C58 \\sim C59: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A 4. Rigid body (RIGU) restrains O7, C56, C57, C58, C59 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 5. Same fragment restrains {O6, C52, C53, C54, C55} sigma for 1-2: 0.02, 1-3: 0.04 as in {O7, C56, C57, C58, C59} 6.a Ternary CH refined with riding coordinates: C2(H2), C27(H27) 6.b Secondary CH2 refined with riding coordinates: C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C18(H18A,H18B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B), C46(H46A,H46B), C47(H47A,H47B), C48(H48A,H48B), C49(H49A,H49B), C50(H50A, H50B), C51(H51A,H51B), C52(H52A,H52B), C53(H53A,H53B), C54(H54A,H54B), C55(H55A,H55B), C56(H56A,H56B), C57(H57A,H57B), C58(H58A,H58B), C59(H59A,H59B) 6.c Aromatic/amide H refined with riding coordinates: C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C21(H21), C23(H23), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42) 6.d Idealised Me refined as rotating group: C25(H25A,H25B,H25C) 6.e Idealised tetrahedral OH refined as rotating group: O1(H1), O3(H3) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary ? loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Na1 Na 0.6512(3) 0.0735(3) 0.54384(6) 0.0297(6) Uani 1 1 d . . . . . O1 O 0.5792(6) 0.0986(6) 0.50441(9) 0.0293(12) Uani 1 1 d . . . . . H1 H 0.526308 0.158444 0.509989 0.035 Uiso 1 1 calc R U . . . O2 O 0.4812(5) 0.2427(5) 0.54231(10) 0.0273(11) Uani 1 1 d . . . . . O3 O 0.6165(5) 0.1407(6) 0.58323(9) 0.0315(12) Uani 1 1 d . . . . . H3 H 0.546054 0.175684 0.577122 0.038 Uiso 1 1 calc R U . . . O4 O 0.5752(9) -0.1459(7) 0.54395(13) 0.0563(18) Uani 1 1 d . . . . . O5 O 0.8774(6) 0.1152(7) 0.54338(12) 0.0465(16) Uani 1 1 d . . . . . N1 N 0.4147(7) 0.2868(6) 0.48450(11) 0.0237(13) Uani 1 1 d . . . . . N2 N 0.4325(7) 0.3138(6) 0.60071(11) 0.0253(13) Uani 1 1 d . . . . . C1 C 0.5971(7) 0.1184(7) 0.47865(12) 0.0214(15) Uani 1 1 d . . . . . C2 C 0.4609(8) 0.1736(8) 0.46804(12) 0.0247(16) Uani 1 1 d . . . . . H2 H 0.391659 0.099001 0.468698 0.030 Uiso 1 1 calc R U . . . C3 C 0.4637(8) 0.2315(9) 0.44169(14) 0.0303(18) Uani 1 1 d . . . . . H3A H 0.379725 0.207005 0.432565 0.036 Uiso 1 1 calc R U . . . H3B H 0.543650 0.197280 0.432422 0.036 Uiso 1 1 calc R U . . . C4 C 0.4730(9) 0.3873(9) 0.44558(14) 0.0318(18) Uani 1 1 d . . . . . H4A H 0.435493 0.437717 0.431253 0.038 Uiso 1 1 calc R U . . . H4B H 0.568134 0.416685 0.448530 0.038 Uiso 1 1 calc R U . . . C5 C 0.3839(9) 0.4066(9) 0.46893(14) 0.0324(19) Uani 1 1 d . . . . . H5A H 0.407983 0.492081 0.477624 0.039 Uiso 1 1 calc R U . . . H5B H 0.286022 0.409195 0.464530 0.039 Uiso 1 1 calc R U . . . C6 C 0.6369(8) -0.0205(7) 0.46869(13) 0.0259(16) Uani 1 1 d . . . . . C7 C 0.5577(9) -0.0905(10) 0.45087(15) 0.038(2) Uani 1 1 d . . . . . H7 H 0.479467 -0.048370 0.443897 0.046 Uiso 1 1 calc R U . . . C8 C 0.5954(10) -0.2233(9) 0.44350(16) 0.038(2) Uani 1 1 d . . . . . H8 H 0.541985 -0.270312 0.431581 0.046 Uiso 1 1 calc R U . . . C9 C 0.7086(10) -0.2851(8) 0.45340(15) 0.0365(19) Uani 1 1 d . . . . . H9 H 0.732709 -0.374808 0.448468 0.044 Uiso 1 1 calc R U . . . C10 C 0.7884(9) -0.2154(8) 0.47076(16) 0.0350(19) Uani 1 1 d . . . . . H10 H 0.867289 -0.257750 0.477450 0.042 Uiso 1 1 calc R U . . . C11 C 0.7527(9) -0.0842(8) 0.47830(15) 0.0305(17) Uani 1 1 d . . . . . H11 H 0.807596 -0.037813 0.490070 0.037 Uiso 1 1 calc R U . . . C12 C 0.7158(8) 0.2200(7) 0.47412(13) 0.0244(16) Uani 1 1 d . . . . . C13 C 0.7398(9) 0.3282(8) 0.49105(15) 0.0330(18) Uani 1 1 d . . . . . H13 H 0.684292 0.337746 0.505344 0.040 Uiso 1 1 calc R U . . . C14 C 0.8432(10) 0.4184(9) 0.48670(16) 0.0385(19) Uani 1 1 d . . . . . H14 H 0.857527 0.490728 0.498084 0.046 Uiso 1 1 calc R U . . . C15 C 0.9288(9) 0.4078(9) 0.46599(16) 0.0341(19) Uani 1 1 d . . . . . H15 H 1.002150 0.469527 0.463573 0.041 Uiso 1 1 calc R U . . . C16 C 0.9027(8) 0.3039(9) 0.44911(16) 0.0361(19) Uani 1 1 d . . . . . H16 H 0.957607 0.296532 0.434683 0.043 Uiso 1 1 calc R U . . . C17 C 0.7984(8) 0.2110(9) 0.45288(15) 0.0320(18) Uani 1 1 d . . . . . H17 H 0.782654 0.140943 0.441096 0.038 Uiso 1 1 calc R U . . . C18 C 0.3011(8) 0.2507(8) 0.50090(13) 0.0249(15) Uani 1 1 d . . . . . H18A H 0.315531 0.157612 0.507476 0.030 Uiso 1 1 calc R U . . . H18B H 0.215148 0.250585 0.491316 0.030 Uiso 1 1 calc R U . . . C19 C 0.3869(7) 0.3369(7) 0.54203(14) 0.0227(14) Uani 1 1 d . . . . . C20 C 0.3727(8) 0.4336(8) 0.56187(12) 0.0236(16) Uani 1 1 d . . . . . C21 C 0.2711(8) 0.5304(7) 0.56146(15) 0.0276(17) Uani 1 1 d . . . . . H21 H 0.263892 0.590939 0.575123 0.033 Uiso 1 1 calc R U . . . C22 C 0.1782(8) 0.5445(8) 0.54212(16) 0.0281(16) Uani 1 1 d . . . . . C23 C 0.1902(8) 0.4485(7) 0.52294(14) 0.0258(16) Uani 1 1 d . . . . . H23 H 0.126252 0.452393 0.509755 0.031 Uiso 1 1 calc R U . . . C24 C 0.2889(8) 0.3494(8) 0.52215(13) 0.0262(16) Uani 1 1 d . . . . . C25 C 0.0655(11) 0.6487(11) 0.54199(18) 0.047(2) Uani 1 1 d . . . . . H25A H -0.022635 0.602322 0.540687 0.071 Uiso 1 1 calc R U . . . H25B H 0.077337 0.709984 0.527837 0.071 Uiso 1 1 calc R U . . . H25C H 0.068522 0.701523 0.557374 0.071 Uiso 1 1 calc R U . . . C26 C 0.6032(7) 0.1344(8) 0.60953(12) 0.0235(16) Uani 1 1 d . . . . . C27 C 0.5433(8) 0.2724(8) 0.61806(12) 0.0234(15) Uani 1 1 d . . . . . H27 H 0.617142 0.342481 0.617231 0.028 Uiso 1 1 calc R U . . . C28 C 0.4798(9) 0.2776(9) 0.64393(13) 0.0342(19) Uani 1 1 d . . . . . H28A H 0.513099 0.201505 0.654313 0.041 Uiso 1 1 calc R U . . . H28B H 0.501230 0.364883 0.652263 0.041 Uiso 1 1 calc R U . . . C29 C 0.3285(9) 0.2649(9) 0.63923(14) 0.0345(19) Uani 1 1 d . . . . . H29A H 0.274757 0.303917 0.653020 0.041 Uiso 1 1 calc R U . . . H29B H 0.301529 0.168621 0.636738 0.041 Uiso 1 1 calc R U . . . C30 C 0.3106(9) 0.3485(9) 0.61532(14) 0.0321(18) Uani 1 1 d . . . . . H30A H 0.226291 0.321989 0.606490 0.038 Uiso 1 1 calc R U . . . H30B H 0.307339 0.447311 0.618961 0.038 Uiso 1 1 calc R U . . . C31 C 0.5070(8) 0.0144(8) 0.61608(15) 0.0297(18) Uani 1 1 d . . . . . C32 C 0.4058(9) -0.0272(8) 0.60000(18) 0.039(2) Uani 1 1 d . . . . . H32 H 0.397198 0.015539 0.584303 0.047 Uiso 1 1 calc R U . . . C33 C 0.3155(10) -0.1317(12) 0.6066(2) 0.060(3) Uani 1 1 d . . . . . H33 H 0.244569 -0.157478 0.595590 0.071 Uiso 1 1 calc R U . . . C34 C 0.3300(11) -0.1990(11) 0.6296(3) 0.070(4) Uani 1 1 d . . . . . H34 H 0.271535 -0.272215 0.634085 0.084 Uiso 1 1 calc R U . . . C35 C 0.4290(10) -0.1562(10) 0.6451(2) 0.053(3) Uani 1 1 d . . . . . H35 H 0.437422 -0.199272 0.660786 0.063 Uiso 1 1 calc R U . . . C36 C 0.5195(10) -0.0517(10) 0.63916(17) 0.042(2) Uani 1 1 d . . . . . H36 H 0.588651 -0.025353 0.650497 0.051 Uiso 1 1 calc R U . . . C37 C 0.7447(7) 0.1053(8) 0.61979(14) 0.0267(17) Uani 1 1 d . . . . . C38 C 0.8164(9) -0.0043(10) 0.60990(16) 0.038(2) Uani 1 1 d . . . . . H38 H 0.776615 -0.057984 0.597167 0.045 Uiso 1 1 calc R U . . . C39 C 0.9476(9) -0.0359(10) 0.61871(19) 0.044(2) Uani 1 1 d . . . . . H39 H 0.995725 -0.110758 0.611784 0.053 Uiso 1 1 calc R U . . . C40 C 1.0071(9) 0.0395(10) 0.63713(18) 0.045(2) Uani 1 1 d . . . . . H40 H 1.096212 0.018559 0.642837 0.053 Uiso 1 1 calc R U . . . C41 C 0.9338(11) 0.1478(12) 0.6473(2) 0.056(3) Uani 1 1 d . . . . . H41 H 0.971852 0.199038 0.660549 0.067 Uiso 1 1 calc R U . . . C42 C 0.8039(10) 0.1816(11) 0.63815(17) 0.044(2) Uani 1 1 d . . . . . H42 H 0.756787 0.257973 0.644728 0.052 Uiso 1 1 calc R U . . . C43 C 0.4710(8) 0.4250(8) 0.58350(13) 0.0248(16) Uani 1 1 d . . . . . H43A H 0.564332 0.408649 0.577194 0.030 Uiso 1 1 calc R U . . . H43B H 0.471195 0.512795 0.592526 0.030 Uiso 1 1 calc R U . . . C44 C 0.4664(12) -0.1936(12) 0.5289(3) 0.067(3) Uani 1 1 d . . . . . H44A H 0.443951 -0.126299 0.515876 0.080 Uiso 1 1 calc R U . . . H44B H 0.384016 -0.210661 0.538999 0.080 Uiso 1 1 calc R U . . . C45 C 0.5174(12) -0.3234(11) 0.51763(18) 0.056(3) Uani 1 1 d . . . . . H45A H 0.543223 -0.309411 0.500100 0.068 Uiso 1 1 calc R U . . . H45B H 0.447118 -0.395606 0.518515 0.068 Uiso 1 1 calc R U . . . C46 C 0.6401(13) -0.3608(12) 0.5330(2) 0.061(3) Uani 1 1 d . . . . . H46A H 0.725197 -0.350800 0.523317 0.073 Uiso 1 1 calc R U . . . H46B H 0.633318 -0.455604 0.539122 0.073 Uiso 1 1 calc R U . . . C47 C 0.6351(16) -0.2583(12) 0.5545(2) 0.073(4) Uani 1 1 d . . . . . H47A H 0.579661 -0.293647 0.568355 0.087 Uiso 1 1 calc R U . . . H47B H 0.727775 -0.236895 0.560551 0.087 Uiso 1 1 calc R U . . . C48 C 0.9955(10) 0.0563(14) 0.5328(2) 0.060(3) Uani 1 1 d . . . . . H48A H 1.022107 0.104896 0.517502 0.073 Uiso 1 1 calc R U . . . H48B H 0.980104 -0.040969 0.528848 0.073 Uiso 1 1 calc R U . . . C49 C 1.1046(10) 0.0717(12) 0.5527(2) 0.055(3) Uani 1 1 d . . . . . H49A H 1.195131 0.087458 0.545127 0.066 Uiso 1 1 calc R U . . . H49B H 1.109210 -0.010750 0.563205 0.066 Uiso 1 1 calc R U . . . C50 C 1.0599(10) 0.1953(11) 0.56783(17) 0.049(3) Uani 1 1 d . . . . . H50A H 1.048552 0.171465 0.585517 0.059 Uiso 1 1 calc R U . . . H50B H 1.126411 0.270723 0.566371 0.059 Uiso 1 1 calc R U . . . C51 C 0.9258(12) 0.2325(11) 0.5562(2) 0.058(3) Uani 1 1 d . . . . . H51A H 0.859775 0.260233 0.569110 0.070 Uiso 1 1 calc R U . . . H51B H 0.937952 0.309386 0.544546 0.070 Uiso 1 1 calc R U . . . O6 O 0.1498(13) -0.3104(9) 0.4522(2) 0.107(4) Uani 1 1 d D . . . . C52 C 0.2192(13) -0.2618(12) 0.47269(19) 0.060(3) Uani 1 1 d D . . . . H52A H 0.318072 -0.256428 0.469218 0.073 Uiso 1 1 calc R U . . . H52B H 0.204927 -0.322980 0.487027 0.073 Uiso 1 1 calc R U . . . C53 C 0.1630(12) -0.1225(10) 0.47808(18) 0.054(3) Uani 1 1 d D . . . . H53A H 0.231648 -0.063877 0.486229 0.064 Uiso 1 1 calc R U . . . H53B H 0.080556 -0.127655 0.488606 0.064 Uiso 1 1 calc R U . . . C54 C 0.1290(12) -0.0713(11) 0.4523(2) 0.064(3) Uani 1 1 d D . . . . H54A H 0.040647 -0.022580 0.452146 0.077 Uiso 1 1 calc R U . . . H54B H 0.200834 -0.009137 0.446076 0.077 Uiso 1 1 calc R U . . . C55 C 0.1219(16) -0.1983(12) 0.4368(2) 0.071(3) Uani 1 1 d D . . . . H55A H 0.030071 -0.207647 0.429431 0.085 Uiso 1 1 calc R U . . . H55B H 0.189486 -0.193676 0.423230 0.085 Uiso 1 1 calc R U . . . O7 O 0.8759(17) 0.5973(15) 0.64367(17) 0.144(6) Uani 1 1 d D U . . . C56 C 0.7715(12) 0.6208(12) 0.6269(2) 0.064(3) Uani 1 1 d D U . . . H56A H 0.742137 0.717260 0.627516 0.077 Uiso 1 1 calc R U . . . H56B H 0.692134 0.561935 0.630617 0.077 Uiso 1 1 calc R U . . . C57 C 0.8314(11) 0.5863(12) 0.60184(18) 0.058(3) Uani 1 1 d D U . . . H57A H 0.764926 0.535529 0.591594 0.069 Uiso 1 1 calc R U . . . H57B H 0.858886 0.669990 0.592896 0.069 Uiso 1 1 calc R U . . . C58 C 0.9516(16) 0.5006(18) 0.6077(2) 0.089(5) Uani 1 1 d D U . . . H58A H 0.929152 0.402565 0.606282 0.107 Uiso 1 1 calc R U . . . H58B H 1.028511 0.521598 0.596452 0.107 Uiso 1 1 calc R U . . . C59 C 0.9851(16) 0.5370(17) 0.6334(3) 0.092(4) Uani 1 1 d D U . . . H59A H 1.009477 0.454133 0.642843 0.110 Uiso 1 1 calc R U . . . H59B H 1.063894 0.599931 0.633691 0.110 Uiso 1 1 calc R U . . . 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 Na1 0.0296(17) 0.0330(18) 0.0265(14) -0.0004(14) 0.0002(13) -0.0012(12) O1 0.031(3) 0.036(3) 0.021(2) -0.004(2) 0.000(2) 0.009(2) O2 0.031(3) 0.026(3) 0.025(2) -0.001(2) 0.002(2) 0.005(2) O3 0.030(3) 0.044(3) 0.021(2) -0.002(2) -0.005(2) 0.014(3) O4 0.089(5) 0.037(4) 0.043(3) 0.004(3) -0.004(4) -0.006(4) O5 0.042(4) 0.051(4) 0.047(3) -0.015(3) 0.003(3) -0.013(3) N1 0.027(3) 0.020(3) 0.024(3) 0.003(2) 0.001(3) 0.008(3) N2 0.023(3) 0.026(3) 0.026(3) 0.003(3) 0.002(3) 0.001(3) C1 0.020(3) 0.026(4) 0.019(3) -0.004(3) -0.001(3) -0.004(3) C2 0.024(4) 0.027(4) 0.023(4) -0.009(3) 0.002(3) -0.006(3) C3 0.029(4) 0.039(5) 0.023(4) -0.005(3) -0.002(3) 0.000(4) C4 0.032(4) 0.037(5) 0.026(4) 0.007(3) 0.003(3) -0.001(4) C5 0.042(5) 0.028(4) 0.027(4) 0.011(3) 0.005(4) 0.010(4) C6 0.039(4) 0.015(3) 0.024(4) 0.001(3) 0.006(3) -0.007(3) C7 0.046(5) 0.041(5) 0.028(4) -0.011(4) -0.004(4) 0.002(4) C8 0.050(5) 0.030(4) 0.035(4) -0.012(4) -0.005(4) 0.004(4) C9 0.051(6) 0.023(4) 0.036(4) -0.007(3) 0.003(4) -0.007(4) C10 0.032(5) 0.024(4) 0.049(5) 0.000(4) 0.001(4) 0.001(3) C11 0.037(5) 0.017(4) 0.037(4) -0.004(3) 0.003(4) -0.001(3) C12 0.034(4) 0.018(4) 0.022(4) -0.001(3) -0.003(3) -0.004(3) C13 0.036(5) 0.025(4) 0.038(4) -0.006(3) -0.007(4) -0.005(3) C14 0.043(5) 0.026(4) 0.047(5) -0.004(4) -0.006(4) -0.005(4) C15 0.031(4) 0.024(4) 0.047(5) -0.007(4) -0.004(4) -0.011(4) C16 0.028(4) 0.036(5) 0.044(5) 0.004(4) 0.001(4) -0.008(4) C17 0.032(4) 0.032(4) 0.032(4) -0.003(3) -0.002(3) -0.010(3) C18 0.025(4) 0.028(4) 0.022(3) -0.003(3) 0.001(3) -0.006(3) C19 0.021(4) 0.021(4) 0.025(3) -0.003(3) 0.000(3) 0.003(3) C20 0.026(4) 0.027(4) 0.018(3) -0.004(3) -0.005(3) -0.005(3) C21 0.037(5) 0.013(3) 0.033(4) -0.002(3) 0.001(3) 0.001(3) C22 0.035(4) 0.020(4) 0.030(4) 0.001(3) 0.002(4) 0.006(3) C23 0.027(4) 0.021(4) 0.029(4) 0.001(3) -0.001(3) 0.006(3) C24 0.031(4) 0.033(4) 0.015(3) -0.002(3) 0.002(3) 0.001(4) C25 0.053(6) 0.051(6) 0.037(4) -0.006(5) -0.003(4) 0.032(4) C26 0.016(4) 0.037(4) 0.017(3) -0.002(3) -0.005(3) 0.005(3) C27 0.029(4) 0.020(4) 0.021(3) 0.002(3) -0.004(3) 0.003(3) C28 0.050(5) 0.038(5) 0.014(4) -0.003(3) -0.001(3) 0.002(4) C29 0.036(5) 0.041(5) 0.027(4) -0.002(4) 0.002(3) 0.003(4) C30 0.034(5) 0.035(5) 0.027(4) 0.001(3) 0.008(3) 0.008(4) C31 0.022(4) 0.022(4) 0.045(5) -0.005(4) 0.000(3) 0.001(3) C32 0.025(4) 0.028(4) 0.064(6) -0.011(4) -0.001(4) -0.012(3) C33 0.031(5) 0.055(7) 0.093(8) -0.029(6) 0.010(5) -0.017(5) C34 0.040(6) 0.036(6) 0.134(11) -0.013(7) 0.021(7) 0.003(5) C35 0.040(6) 0.033(5) 0.086(8) 0.012(5) 0.009(5) 0.003(4) C36 0.034(5) 0.043(5) 0.051(5) 0.010(4) 0.003(4) 0.000(4) C37 0.018(4) 0.031(4) 0.031(4) 0.005(3) -0.004(3) -0.002(3) C38 0.026(4) 0.045(5) 0.042(5) 0.003(4) -0.002(4) 0.003(4) C39 0.027(5) 0.038(5) 0.067(6) 0.012(5) 0.004(4) 0.005(4) C40 0.022(4) 0.045(6) 0.067(6) 0.019(5) -0.011(4) 0.005(4) C41 0.046(6) 0.058(7) 0.063(6) 0.014(5) -0.029(5) -0.011(5) C42 0.036(5) 0.052(6) 0.043(5) -0.001(4) -0.017(4) -0.001(4) C43 0.028(4) 0.023(4) 0.023(4) 0.001(3) -0.006(3) -0.004(3) C44 0.043(6) 0.046(7) 0.112(10) 0.010(6) -0.008(6) -0.010(5) C45 0.070(7) 0.060(7) 0.039(5) 0.005(5) 0.007(5) -0.043(6) C46 0.065(7) 0.052(7) 0.066(7) 0.009(5) 0.017(6) 0.006(5) C47 0.110(11) 0.047(7) 0.061(7) 0.000(6) -0.019(7) -0.008(7) C48 0.027(5) 0.102(10) 0.052(6) -0.032(6) -0.002(4) 0.011(5) C49 0.028(5) 0.064(7) 0.072(7) 0.013(6) -0.003(5) -0.018(5) C50 0.047(6) 0.057(7) 0.043(5) -0.004(5) 0.006(4) -0.029(5) C51 0.056(7) 0.040(6) 0.078(7) -0.017(5) 0.004(6) -0.023(5) O6 0.154(11) 0.046(5) 0.121(8) -0.021(5) -0.044(8) 0.019(6) C52 0.064(7) 0.062(7) 0.055(6) 0.008(5) -0.002(6) 0.013(6) C53 0.069(7) 0.045(6) 0.047(5) -0.002(5) -0.007(5) -0.011(5) C54 0.056(7) 0.039(6) 0.096(9) 0.018(6) -0.024(7) -0.011(5) C55 0.100(10) 0.055(7) 0.057(7) -0.008(6) -0.015(7) 0.013(7) O7 0.217(14) 0.159(12) 0.054(5) -0.004(6) -0.015(7) 0.092(11) C56 0.064(7) 0.049(6) 0.080(7) -0.011(5) 0.022(5) -0.008(5) C57 0.055(6) 0.072(7) 0.046(5) 0.007(5) -0.006(4) -0.011(5) C58 0.091(10) 0.124(12) 0.052(6) 0.021(7) 0.002(6) 0.043(8) C59 0.100(10) 0.087(10) 0.089(9) 0.001(8) -0.040(8) -0.001(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Na1 O1 2.258(6) . ? Na1 O2 2.355(5) . ? Na1 O3 2.254(6) . ? Na1 O4 2.278(7) . ? Na1 O5 2.258(7) . ? O1 H1 0.8400 . ? O1 C1 1.416(8) . ? O2 C19 1.308(8) . ? O3 H3 0.8400 . ? O3 C26 1.428(8) . ? O4 C44 1.422(14) . ? O4 C47 1.372(13) . ? O5 C48 1.415(11) . ? O5 C51 1.426(11) . ? N1 C2 1.494(9) . ? N1 C5 1.476(9) . ? N1 C18 1.468(10) . ? N2 C27 1.492(9) . ? N2 C30 1.473(10) . ? N2 C43 1.483(10) . ? C1 C2 1.552(10) . ? C1 C6 1.517(10) . ? C1 C12 1.552(10) . ? C2 H2 1.0000 . ? C2 C3 1.533(10) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C3 C4 1.545(12) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4 C5 1.547(11) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.415(11) . ? C6 C11 1.397(12) . ? C7 H7 0.9500 . ? C7 C8 1.411(12) . ? C8 H8 0.9500 . ? C8 C9 1.374(13) . ? C9 H9 0.9500 . ? C9 C10 1.400(12) . ? C10 H10 0.9500 . ? C10 C11 1.395(11) . ? C11 H11 0.9500 . ? C12 C13 1.421(10) . ? C12 C17 1.408(11) . ? C13 H13 0.9500 . ? C13 C14 1.366(12) . ? C14 H14 0.9500 . ? C14 C15 1.403(13) . ? C15 H15 0.9500 . ? C15 C16 1.392(12) . ? C16 H16 0.9500 . ? C16 C17 1.386(11) . ? C17 H17 0.9500 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C18 C24 1.507(10) . ? C19 C20 1.438(10) . ? C19 C24 1.447(10) . ? C20 C21 1.378(11) . ? C20 C43 1.518(10) . ? C21 H21 0.9500 . ? C21 C22 1.393(12) . ? C22 C23 1.405(11) . ? C22 C25 1.507(10) . ? C23 H23 0.9500 . ? C23 C24 1.374(10) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C27 1.547(11) . ? C26 C31 1.550(11) . ? C26 C37 1.522(10) . ? C27 H27 1.0000 . ? C27 C28 1.531(10) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C28 C29 1.512(12) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C29 C30 1.540(11) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C32 1.382(12) . ? C31 C36 1.411(12) . ? C32 H32 0.9500 . ? C32 C33 1.401(13) . ? C33 H33 0.9500 . ? C33 C34 1.417(19) . ? C34 H34 0.9500 . ? C34 C35 1.348(17) . ? C35 H35 0.9500 . ? C35 C36 1.395(14) . ? C36 H36 0.9500 . ? C37 C38 1.392(12) . ? C37 C42 1.372(12) . ? C38 H38 0.9500 . ? C38 C39 1.408(12) . ? C39 H39 0.9500 . ? C39 C40 1.371(14) . ? C40 H40 0.9500 . ? C40 C41 1.397(16) . ? C41 H41 0.9500 . ? C41 C42 1.407(13) . ? C42 H42 0.9500 . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C44 C45 1.498(17) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C45 C46 1.507(16) . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ? C46 C47 1.537(16) . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? C48 C49 1.524(13) . ? C49 H49A 0.9900 . ? C49 H49B 0.9900 . ? C49 C50 1.527(16) . ? C50 H50A 0.9900 . ? C50 H50B 0.9900 . ? C50 C51 1.503(16) . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? O6 C52 1.386(13) . ? O6 C55 1.405(13) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C52 C53 1.502(15) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C53 C54 1.520(14) . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? C54 C55 1.502(14) . ? C55 H55A 0.9900 . ? C55 H55B 0.9900 . ? O7 C56 1.386(15) . ? O7 C59 1.344(17) . ? C56 H56A 0.9900 . ? C56 H56B 0.9900 . ? C56 C57 1.516(14) . ? C57 H57A 0.9900 . ? C57 H57B 0.9900 . ? C57 C58 1.483(16) . ? C58 H58A 0.9900 . ? C58 H58B 0.9900 . ? C58 C59 1.471(16) . ? C59 H59A 0.9900 . ? C59 H59B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Na1 O2 70.6(2) . . ? O1 Na1 O4 90.2(3) . . ? O3 Na1 O1 144.3(2) . . ? O3 Na1 O2 73.7(2) . . ? O3 Na1 O4 103.0(3) . . ? O3 Na1 O5 96.1(2) . . ? O4 Na1 O2 115.7(3) . . ? O5 Na1 O1 106.1(3) . . ? O5 Na1 O2 124.6(3) . . ? O5 Na1 O4 119.6(3) . . ? Na1 O1 H1 86.0 . . ? C1 O1 Na1 154.6(5) . . ? C1 O1 H1 109.5 . . ? C19 O2 Na1 178.6(5) . . ? Na1 O3 H3 82.7 . . ? C26 O3 Na1 160.1(5) . . ? C26 O3 H3 109.5 . . ? C44 O4 Na1 123.8(6) . . ? C47 O4 Na1 128.3(8) . . ? C47 O4 C44 107.0(9) . . ? C48 O5 Na1 137.4(6) . . ? C48 O5 C51 104.7(8) . . ? C51 O5 Na1 118.0(6) . . ? C5 N1 C2 108.4(5) . . ? C18 N1 C2 114.2(6) . . ? C18 N1 C5 112.4(6) . . ? C30 N2 C27 108.5(6) . . ? C30 N2 C43 111.9(6) . . ? C43 N2 C27 114.1(6) . . ? O1 C1 C2 107.7(6) . . ? O1 C1 C6 104.9(6) . . ? O1 C1 C12 109.7(5) . . ? C2 C1 C12 111.3(6) . . ? C6 C1 C2 113.8(6) . . ? C6 C1 C12 109.2(6) . . ? N1 C2 C1 107.5(5) . . ? N1 C2 H2 108.5 . . ? N1 C2 C3 106.4(6) . . ? C1 C2 H2 108.5 . . ? C3 C2 C1 117.2(6) . . ? C3 C2 H2 108.5 . . ? C2 C3 H3A 111.0 . . ? C2 C3 H3B 111.0 . . ? C2 C3 C4 104.0(6) . . ? H3A C3 H3B 109.0 . . ? C4 C3 H3A 111.0 . . ? C4 C3 H3B 111.0 . . ? C3 C4 H4A 111.5 . . ? C3 C4 H4B 111.5 . . ? C3 C4 C5 101.5(7) . . ? H4A C4 H4B 109.3 . . ? C5 C4 H4A 111.5 . . ? C5 C4 H4B 111.5 . . ? N1 C5 C4 104.6(6) . . ? N1 C5 H5A 110.8 . . ? N1 C5 H5B 110.8 . . ? C4 C5 H5A 110.8 . . ? C4 C5 H5B 110.8 . . ? H5A C5 H5B 108.9 . . ? C7 C6 C1 122.5(7) . . ? C11 C6 C1 118.7(6) . . ? C11 C6 C7 118.8(7) . . ? C6 C7 H7 120.1 . . ? C8 C7 C6 119.7(8) . . ? C8 C7 H7 120.1 . . ? C7 C8 H8 119.7 . . ? C9 C8 C7 120.6(8) . . ? C9 C8 H8 119.7 . . ? C8 C9 H9 120.1 . . ? C8 C9 C10 119.8(8) . . ? C10 C9 H9 120.1 . . ? C9 C10 H10 119.8 . . ? C11 C10 C9 120.4(8) . . ? C11 C10 H10 119.8 . . ? C6 C11 H11 119.7 . . ? C10 C11 C6 120.6(7) . . ? C10 C11 H11 119.7 . . ? C13 C12 C1 120.2(7) . . ? C17 C12 C1 121.3(6) . . ? C17 C12 C13 118.4(7) . . ? C12 C13 H13 120.1 . . ? C14 C13 C12 119.8(8) . . ? C14 C13 H13 120.1 . . ? C13 C14 H14 118.9 . . ? C13 C14 C15 122.3(8) . . ? C15 C14 H14 118.9 . . ? C14 C15 H15 121.1 . . ? C16 C15 C14 117.8(8) . . ? C16 C15 H15 121.1 . . ? C15 C16 H16 119.3 . . ? C17 C16 C15 121.4(8) . . ? C17 C16 H16 119.3 . . ? C12 C17 H17 119.9 . . ? C16 C17 C12 120.3(8) . . ? C16 C17 H17 119.9 . . ? N1 C18 H18A 109.3 . . ? N1 C18 H18B 109.3 . . ? N1 C18 C24 111.4(6) . . ? H18A C18 H18B 108.0 . . ? C24 C18 H18A 109.3 . . ? C24 C18 H18B 109.3 . . ? O2 C19 C20 121.8(7) . . ? O2 C19 C24 122.6(7) . . ? C20 C19 C24 115.7(6) . . ? C19 C20 C43 118.4(7) . . ? C21 C20 C19 120.9(7) . . ? C21 C20 C43 120.7(7) . . ? C20 C21 H21 118.2 . . ? C20 C21 C22 123.6(7) . . ? C22 C21 H21 118.2 . . ? C21 C22 C23 115.6(6) . . ? C21 C22 C25 123.4(8) . . ? C23 C22 C25 120.9(8) . . ? C22 C23 H23 118.1 . . ? C24 C23 C22 123.8(7) . . ? C24 C23 H23 118.1 . . ? C19 C24 C18 117.3(6) . . ? C23 C24 C18 122.4(7) . . ? C23 C24 C19 120.4(7) . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25B 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O3 C26 C27 107.1(6) . . ? O3 C26 C31 108.4(6) . . ? O3 C26 C37 106.7(6) . . ? C27 C26 C31 111.4(6) . . ? C37 C26 C27 113.8(6) . . ? C37 C26 C31 109.3(6) . . ? N2 C27 C26 109.2(6) . . ? N2 C27 H27 108.2 . . ? N2 C27 C28 105.5(6) . . ? C26 C27 H27 108.2 . . ? C28 C27 C26 117.1(6) . . ? C28 C27 H27 108.2 . . ? C27 C28 H28A 110.9 . . ? C27 C28 H28B 110.9 . . ? H28A C28 H28B 109.0 . . ? C29 C28 C27 104.1(6) . . ? C29 C28 H28A 110.9 . . ? C29 C28 H28B 110.9 . . ? C28 C29 H29A 111.4 . . ? C28 C29 H29B 111.4 . . ? C28 C29 C30 102.0(7) . . ? H29A C29 H29B 109.2 . . ? C30 C29 H29A 111.4 . . ? C30 C29 H29B 111.4 . . ? N2 C30 C29 103.5(6) . . ? N2 C30 H30A 111.1 . . ? N2 C30 H30B 111.1 . . ? C29 C30 H30A 111.1 . . ? C29 C30 H30B 111.1 . . ? H30A C30 H30B 109.0 . . ? C32 C31 C26 121.3(7) . . ? C32 C31 C36 118.8(8) . . ? C36 C31 C26 119.9(7) . . ? C31 C32 H32 119.6 . . ? C31 C32 C33 120.8(10) . . ? C33 C32 H32 119.6 . . ? C32 C33 H33 119.9 . . ? C32 C33 C34 120.1(10) . . ? C34 C33 H33 119.9 . . ? C33 C34 H34 120.9 . . ? C35 C34 C33 118.1(11) . . ? C35 C34 H34 120.9 . . ? C34 C35 H35 118.5 . . ? C34 C35 C36 123.0(11) . . ? C36 C35 H35 118.5 . . ? C31 C36 H36 120.4 . . ? C35 C36 C31 119.1(9) . . ? C35 C36 H36 120.4 . . ? C38 C37 C26 117.8(7) . . ? C42 C37 C26 123.2(8) . . ? C42 C37 C38 119.0(8) . . ? C37 C38 H38 119.9 . . ? C37 C38 C39 120.2(9) . . ? C39 C38 H38 119.9 . . ? C38 C39 H39 119.5 . . ? C40 C39 C38 121.1(9) . . ? C40 C39 H39 119.5 . . ? C39 C40 H40 120.7 . . ? C39 C40 C41 118.6(8) . . ? C41 C40 H40 120.7 . . ? C40 C41 H41 119.8 . . ? C40 C41 C42 120.4(10) . . ? C42 C41 H41 119.8 . . ? C37 C42 C41 120.7(10) . . ? C37 C42 H42 119.7 . . ? C41 C42 H42 119.7 . . ? N2 C43 C20 111.2(6) . . ? N2 C43 H43A 109.4 . . ? N2 C43 H43B 109.4 . . ? C20 C43 H43A 109.4 . . ? C20 C43 H43B 109.4 . . ? H43A C43 H43B 108.0 . . ? O4 C44 H44A 110.7 . . ? O4 C44 H44B 110.7 . . ? O4 C44 C45 105.2(9) . . ? H44A C44 H44B 108.8 . . ? C45 C44 H44A 110.7 . . ? C45 C44 H44B 110.7 . . ? C44 C45 H45A 110.9 . . ? C44 C45 H45B 110.9 . . ? C44 C45 C46 104.5(9) . . ? H45A C45 H45B 108.9 . . ? C46 C45 H45A 110.9 . . ? C46 C45 H45B 110.9 . . ? C45 C46 H46A 111.1 . . ? C45 C46 H46B 111.1 . . ? C45 C46 C47 103.3(10) . . ? H46A C46 H46B 109.1 . . ? C47 C46 H46A 111.1 . . ? C47 C46 H46B 111.1 . . ? O4 C47 C46 103.2(9) . . ? O4 C47 H47A 111.1 . . ? O4 C47 H47B 111.1 . . ? C46 C47 H47A 111.1 . . ? C46 C47 H47B 111.1 . . ? H47A C47 H47B 109.1 . . ? O5 C48 H48A 110.8 . . ? O5 C48 H48B 110.8 . . ? O5 C48 C49 104.5(8) . . ? H48A C48 H48B 108.9 . . ? C49 C48 H48A 110.8 . . ? C49 C48 H48B 110.8 . . ? C48 C49 H49A 110.8 . . ? C48 C49 H49B 110.8 . . ? C48 C49 C50 104.8(9) . . ? H49A C49 H49B 108.9 . . ? C50 C49 H49A 110.8 . . ? C50 C49 H49B 110.8 . . ? C49 C50 H50A 111.2 . . ? C49 C50 H50B 111.2 . . ? H50A C50 H50B 109.1 . . ? C51 C50 C49 102.8(8) . . ? C51 C50 H50A 111.2 . . ? C51 C50 H50B 111.2 . . ? O5 C51 C50 107.4(9) . . ? O5 C51 H51A 110.2 . . ? O5 C51 H51B 110.2 . . ? C50 C51 H51A 110.2 . . ? C50 C51 H51B 110.2 . . ? H51A C51 H51B 108.5 . . ? C52 O6 C55 107.4(9) . . ? O6 C52 H52A 110.4 . . ? O6 C52 H52B 110.4 . . ? O6 C52 C53 106.7(9) . . ? H52A C52 H52B 108.6 . . ? C53 C52 H52A 110.4 . . ? C53 C52 H52B 110.4 . . ? C52 C53 H53A 111.4 . . ? C52 C53 H53B 111.4 . . ? C52 C53 C54 101.8(8) . . ? H53A C53 H53B 109.3 . . ? C54 C53 H53A 111.4 . . ? C54 C53 H53B 111.4 . . ? C53 C54 H54A 110.9 . . ? C53 C54 H54B 110.9 . . ? H54A C54 H54B 108.9 . . ? C55 C54 C53 104.2(8) . . ? C55 C54 H54A 110.9 . . ? C55 C54 H54B 110.9 . . ? O6 C55 C54 108.3(9) . . ? O6 C55 H55A 110.0 . . ? O6 C55 H55B 110.0 . . ? C54 C55 H55A 110.0 . . ? C54 C55 H55B 110.0 . . ? H55A C55 H55B 108.4 . . ? C59 O7 C56 113.1(10) . . ? O7 C56 H56A 110.7 . . ? O7 C56 H56B 110.7 . . ? O7 C56 C57 105.1(9) . . ? H56A C56 H56B 108.8 . . ? C57 C56 H56A 110.7 . . ? C57 C56 H56B 110.7 . . ? C56 C57 H57A 110.9 . . ? C56 C57 H57B 110.9 . . ? H57A C57 H57B 108.9 . . ? C58 C57 C56 104.1(9) . . ? C58 C57 H57A 110.9 . . ? C58 C57 H57B 110.9 . . ? C57 C58 H58A 111.0 . . ? C57 C58 H58B 111.0 . . ? H58A C58 H58B 109.0 . . ? C59 C58 C57 103.9(11) . . ? C59 C58 H58A 111.0 . . ? C59 C58 H58B 111.0 . . ? O7 C59 C58 108.6(12) . . ? O7 C59 H59A 110.0 . . ? O7 C59 H59B 110.0 . . ? C58 C59 H59A 110.0 . . ? C58 C59 H59B 110.0 . . ? H59A C59 H59B 108.3 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O1 H1 O2 0.84 1.98 2.668(7) 138.2 . yes O3 H3 O2 0.84 2.09 2.767(7) 137.1 . yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Na1 O1 C1 C2 -159.0(9) . . . . ? Na1 O1 C1 C6 79.5(12) . . . . ? Na1 O1 C1 C12 -37.7(14) . . . . ? Na1 O3 C26 C27 -169.3(11) . . . . ? Na1 O3 C26 C31 -48.9(15) . . . . ? Na1 O3 C26 C37 68.6(15) . . . . ? Na1 O4 C44 C45 133.1(7) . . . . ? Na1 O4 C47 C46 -127.5(8) . . . . ? Na1 O5 C48 C49 -142.0(8) . . . . ? Na1 O5 C51 C50 142.9(7) . . . . ? O1 C1 C2 N1 47.6(7) . . . . ? O1 C1 C2 C3 167.3(6) . . . . ? O1 C1 C6 C7 119.0(8) . . . . ? O1 C1 C6 C11 -58.1(8) . . . . ? O1 C1 C12 C13 -33.6(10) . . . . ? O1 C1 C12 C17 148.9(7) . . . . ? O2 C19 C20 C21 -178.7(7) . . . . ? O2 C19 C20 C43 0.3(12) . . . . ? O2 C19 C24 C18 -1.7(12) . . . . ? O2 C19 C24 C23 178.7(8) . . . . ? O3 C26 C27 N2 42.4(7) . . . . ? O3 C26 C27 C28 162.2(6) . . . . ? O3 C26 C31 C32 -28.8(10) . . . . ? O3 C26 C31 C36 153.1(7) . . . . ? O3 C26 C37 C38 -51.4(9) . . . . ? O3 C26 C37 C42 128.6(8) . . . . ? O4 C44 C45 C46 15.6(11) . . . . ? O5 C48 C49 C50 -26.3(12) . . . . ? N1 C2 C3 C4 21.4(8) . . . . ? N1 C18 C24 C19 -75.8(9) . . . . ? N1 C18 C24 C23 103.8(8) . . . . ? N2 C27 C28 C29 22.4(9) . . . . ? C1 C2 C3 C4 -98.9(8) . . . . ? C1 C6 C7 C8 -176.0(7) . . . . ? C1 C6 C11 C10 176.2(7) . . . . ? C1 C12 C13 C14 -179.0(8) . . . . ? C1 C12 C17 C16 179.2(7) . . . . ? C2 N1 C5 C4 -25.7(8) . . . . ? C2 N1 C18 C24 161.7(6) . . . . ? C2 C1 C6 C7 1.6(10) . . . . ? C2 C1 C6 C11 -175.5(6) . . . . ? C2 C1 C12 C13 85.5(8) . . . . ? C2 C1 C12 C17 -92.0(9) . . . . ? C2 C3 C4 C5 -36.0(8) . . . . ? C3 C4 C5 N1 38.0(8) . . . . ? C5 N1 C2 C1 129.0(7) . . . . ? C5 N1 C2 C3 2.6(8) . . . . ? C5 N1 C18 C24 -74.3(8) . . . . ? C6 C1 C2 N1 163.5(6) . . . . ? C6 C1 C2 C3 -76.8(8) . . . . ? C6 C1 C12 C13 -148.0(7) . . . . ? C6 C1 C12 C17 34.5(10) . . . . ? C6 C7 C8 C9 -0.2(13) . . . . ? C7 C6 C11 C10 -1.0(11) . . . . ? C7 C8 C9 C10 -0.7(13) . . . . ? C8 C9 C10 C11 0.8(13) . . . . ? C9 C10 C11 C6 0.1(12) . . . . ? C11 C6 C7 C8 1.1(12) . . . . ? C12 C1 C2 N1 -72.6(7) . . . . ? C12 C1 C2 C3 47.1(8) . . . . ? C12 C1 C6 C7 -123.5(8) . . . . ? C12 C1 C6 C11 59.4(8) . . . . ? C12 C13 C14 C15 -0.6(14) . . . . ? C13 C12 C17 C16 1.6(12) . . . . ? C13 C14 C15 C16 2.3(14) . . . . ? C14 C15 C16 C17 -2.0(13) . . . . ? C15 C16 C17 C12 0.0(13) . . . . ? C17 C12 C13 C14 -1.3(12) . . . . ? C18 N1 C2 C1 -104.8(7) . . . . ? C18 N1 C2 C3 128.8(6) . . . . ? C18 N1 C5 C4 -152.9(6) . . . . ? C19 C20 C21 C22 -1.5(12) . . . . ? C19 C20 C43 N2 -78.4(9) . . . . ? C20 C19 C24 C18 179.5(6) . . . . ? C20 C19 C24 C23 -0.1(11) . . . . ? C20 C21 C22 C23 2.6(13) . . . . ? C20 C21 C22 C25 178.7(9) . . . . ? C21 C20 C43 N2 100.7(8) . . . . ? C21 C22 C23 C24 -2.6(13) . . . . ? C22 C23 C24 C18 -178.2(8) . . . . ? C22 C23 C24 C19 1.4(12) . . . . ? C24 C19 C20 C21 0.1(12) . . . . ? C24 C19 C20 C43 179.2(6) . . . . ? C25 C22 C23 C24 -178.8(9) . . . . ? C26 C27 C28 C29 -99.3(8) . . . . ? C26 C31 C32 C33 -177.1(8) . . . . ? C26 C31 C36 C35 177.7(8) . . . . ? C26 C37 C38 C39 -179.9(8) . . . . ? C26 C37 C42 C41 178.4(8) . . . . ? C27 N2 C30 C29 -25.9(8) . . . . ? C27 N2 C43 C20 163.2(6) . . . . ? C27 C26 C31 C32 88.7(9) . . . . ? C27 C26 C31 C36 -89.3(8) . . . . ? C27 C26 C37 C38 -169.2(7) . . . . ? C27 C26 C37 C42 10.8(11) . . . . ? C27 C28 C29 C30 -37.6(8) . . . . ? C28 C29 C30 N2 39.2(8) . . . . ? C30 N2 C27 C26 129.2(7) . . . . ? C30 N2 C27 C28 2.6(8) . . . . ? C30 N2 C43 C20 -73.1(8) . . . . ? C31 C26 C27 N2 -75.9(7) . . . . ? C31 C26 C27 C28 43.8(9) . . . . ? C31 C26 C37 C38 65.5(9) . . . . ? C31 C26 C37 C42 -114.5(8) . . . . ? C31 C32 C33 C34 -1.9(15) . . . . ? C32 C31 C36 C35 -0.4(13) . . . . ? C32 C33 C34 C35 2.3(16) . . . . ? C33 C34 C35 C36 -1.8(16) . . . . ? C34 C35 C36 C31 0.8(15) . . . . ? C36 C31 C32 C33 1.0(13) . . . . ? C37 C26 C27 N2 160.0(6) . . . . ? C37 C26 C27 C28 -80.2(8) . . . . ? C37 C26 C31 C32 -144.7(8) . . . . ? C37 C26 C31 C36 37.3(10) . . . . ? C37 C38 C39 C40 0.2(14) . . . . ? C38 C37 C42 C41 -1.6(13) . . . . ? C38 C39 C40 C41 0.9(14) . . . . ? C39 C40 C41 C42 -2.5(15) . . . . ? C40 C41 C42 C37 2.8(15) . . . . ? C42 C37 C38 C39 0.1(13) . . . . ? C43 N2 C27 C26 -105.3(7) . . . . ? C43 N2 C27 C28 128.1(7) . . . . ? C43 N2 C30 C29 -152.7(6) . . . . ? C43 C20 C21 C22 179.5(7) . . . . ? C44 O4 C47 C46 42.1(13) . . . . ? C44 C45 C46 C47 8.3(11) . . . . ? C45 C46 C47 O4 -30.4(12) . . . . ? C47 O4 C44 C45 -37.2(12) . . . . ? C48 O5 C51 C50 -38.4(11) . . . . ? C48 C49 C50 C51 3.5(11) . . . . ? C49 C50 C51 O5 20.5(11) . . . . ? C51 O5 C48 C49 39.7(11) . . . . ? O6 C52 C53 C54 -32.9(13) . . . . ? C52 O6 C55 C54 -20.9(16) . . . . ? C52 C53 C54 C55 19.3(13) . . . . ? C53 C54 C55 O6 -0.4(15) . . . . ? C55 O6 C52 C53 34.2(14) . . . . ? O7 C56 C57 C58 19.1(15) . . . . ? C56 O7 C59 C58 -6(2) . . . . ? C56 C57 C58 C59 -22.3(16) . . . . ? C57 C58 C59 O7 18.4(19) . . . . ? C59 O7 C56 C57 -8.2(18) . . . . ? _shelx_res_file ; TITL 1_reint_smar_a.res in P4(3) 1.res created by SHELXL-2018/3 at 15:29:09 on 19-Dec-2019 REM Old TITL 1_reint_smar in P4(3) REM SHELXT solution in P4(3): R1 0.241, Rweak 0.214, Alpha 0.036 REM 0.836 for 48 systematic absences, Orientation as input REM Flack x = 0.482 ( 0.028 ) from 3587 Parsons' quotients REM Formula found by SHELXT: C48 N16 O4 Na CELL 1.54184 9.814211 9.814211 54.027124 90 90 90 ZERR 4 0.000387 0.000387 0.001216 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM -Y,+X,0.75+Z SYMM +Y,-X,0.25+Z SFAC C H N Na O UNIT 236 308 8 4 28 SIMU O7 > C59 RIGU O7 > C59 L.S. 16 PLAN 20 TEMP -153.15 CONF HTAB O1 O2 HTAB O3 O2 FREE Na1 H3 FREE Na1 H1 BOND list 7 list 4 MORE -1 BOND $H fmap 2 53 acta htab SHEL 0.83 999 OMIT 1 4 1 OMIT -1 -2 1 OMIT 6 -9 -9 OMIT -6 7 40 OMIT 0 4 1 OMIT 1 3 7 REM REM REM WGHT 0.111700 BASF 0.50033 FVAR 1.63686 NA1 4 0.651192 0.073475 0.543842 11.00000 0.02956 0.03304 = 0.02655 -0.00037 0.00022 -0.00118 O1 5 0.579201 0.098579 0.504407 11.00000 0.03092 0.03573 = 0.02114 -0.00437 0.00010 0.00906 AFIX 147 H1 2 0.526308 0.158444 0.509989 11.00000 -1.20000 AFIX 0 O2 5 0.481186 0.242658 0.542313 11.00000 0.03071 0.02571 = 0.02546 -0.00082 0.00178 0.00519 O3 5 0.616549 0.140694 0.583233 11.00000 0.02979 0.04415 = 0.02064 -0.00220 -0.00458 0.01397 AFIX 147 H3 2 0.546054 0.175684 0.577122 11.00000 -1.20000 AFIX 0 O4 5 0.575233 -0.145882 0.543950 11.00000 0.08906 0.03683 = 0.04294 0.00398 -0.00357 -0.00637 O5 5 0.877414 0.115202 0.543376 11.00000 0.04172 0.05094 = 0.04671 -0.01500 0.00319 -0.01339 N1 3 0.414666 0.286840 0.484495 11.00000 0.02707 0.02041 = 0.02363 0.00276 0.00097 0.00755 N2 3 0.432478 0.313760 0.600706 11.00000 0.02329 0.02634 = 0.02622 0.00295 0.00187 0.00111 C1 1 0.597138 0.118440 0.478654 11.00000 0.01962 0.02597 = 0.01850 -0.00402 -0.00095 -0.00394 C2 1 0.460939 0.173627 0.468036 11.00000 0.02416 0.02664 = 0.02323 -0.00918 0.00206 -0.00572 AFIX 13 H2 2 0.391659 0.099001 0.468698 11.00000 -1.20000 AFIX 0 C3 1 0.463677 0.231550 0.441694 11.00000 0.02865 0.03929 = 0.02294 -0.00546 -0.00222 0.00000 AFIX 23 H3A 2 0.379725 0.207005 0.432565 11.00000 -1.20000 H3B 2 0.543650 0.197280 0.432422 11.00000 -1.20000 AFIX 0 C4 1 0.473018 0.387271 0.445582 11.00000 0.03196 0.03718 = 0.02639 0.00692 0.00261 -0.00061 AFIX 23 H4A 2 0.435493 0.437717 0.431253 11.00000 -1.20000 H4B 2 0.568134 0.416685 0.448530 11.00000 -1.20000 AFIX 0 C5 1 0.383905 0.406599 0.468934 11.00000 0.04223 0.02775 = 0.02733 0.01087 0.00500 0.00995 AFIX 23 H5A 2 0.407983 0.492081 0.477624 11.00000 -1.20000 H5B 2 0.286022 0.409195 0.464530 11.00000 -1.20000 AFIX 0 C6 1 0.636856 -0.020516 0.468693 11.00000 0.03881 0.01546 = 0.02356 0.00069 0.00578 -0.00739 C7 1 0.557685 -0.090537 0.450871 11.00000 0.04628 0.04084 = 0.02829 -0.01087 -0.00368 0.00248 AFIX 43 H7 2 0.479467 -0.048370 0.443897 11.00000 -1.20000 AFIX 0 C8 1 0.595387 -0.223257 0.443498 11.00000 0.05036 0.02999 = 0.03452 -0.01212 -0.00466 0.00391 AFIX 43 H8 2 0.541985 -0.270312 0.431581 11.00000 -1.20000 AFIX 0 C9 1 0.708627 -0.285065 0.453397 11.00000 0.05124 0.02251 = 0.03588 -0.00652 0.00268 -0.00728 AFIX 43 H9 2 0.732709 -0.374808 0.448468 11.00000 -1.20000 AFIX 0 C10 1 0.788399 -0.215432 0.470762 11.00000 0.03242 0.02385 = 0.04864 0.00046 0.00051 0.00095 AFIX 43 H10 2 0.867289 -0.257750 0.477450 11.00000 -1.20000 AFIX 0 C11 1 0.752680 -0.084241 0.478300 11.00000 0.03701 0.01722 = 0.03717 -0.00381 0.00341 -0.00102 AFIX 43 H11 2 0.807596 -0.037813 0.490070 11.00000 -1.20000 AFIX 0 C12 1 0.715802 0.220029 0.474123 11.00000 0.03402 0.01761 = 0.02161 -0.00097 -0.00294 -0.00397 C13 1 0.739849 0.328176 0.491050 11.00000 0.03613 0.02530 = 0.03767 -0.00587 -0.00705 -0.00450 AFIX 43 H13 2 0.684292 0.337746 0.505344 11.00000 -1.20000 AFIX 0 C14 1 0.843172 0.418374 0.486698 11.00000 0.04296 0.02568 = 0.04683 -0.00363 -0.00646 -0.00483 AFIX 43 H14 2 0.857527 0.490728 0.498084 11.00000 -1.20000 AFIX 0 C15 1 0.928788 0.407795 0.465990 11.00000 0.03135 0.02448 = 0.04660 -0.00705 -0.00420 -0.01051 AFIX 43 H15 2 1.002150 0.469527 0.463573 11.00000 -1.20000 AFIX 0 C16 1 0.902733 0.303913 0.449106 11.00000 0.02768 0.03617 = 0.04445 0.00350 0.00070 -0.00798 AFIX 43 H16 2 0.957607 0.296532 0.434683 11.00000 -1.20000 AFIX 0 C17 1 0.798445 0.211006 0.452885 11.00000 0.03229 0.03218 = 0.03153 -0.00348 -0.00171 -0.01029 AFIX 43 H17 2 0.782654 0.140943 0.441096 11.00000 -1.20000 AFIX 0 C18 1 0.301114 0.250665 0.500903 11.00000 0.02526 0.02790 = 0.02159 -0.00286 0.00149 -0.00575 AFIX 23 H18A 2 0.315531 0.157612 0.507476 11.00000 -1.20000 H18B 2 0.215148 0.250585 0.491316 11.00000 -1.20000 AFIX 0 C19 1 0.386927 0.336917 0.542033 11.00000 0.02131 0.02138 = 0.02532 -0.00348 0.00024 0.00295 C20 1 0.372729 0.433583 0.561870 11.00000 0.02565 0.02712 = 0.01802 -0.00363 -0.00501 -0.00482 C21 1 0.271067 0.530421 0.561461 11.00000 0.03678 0.01264 = 0.03349 -0.00187 0.00063 0.00132 AFIX 43 H21 2 0.263892 0.590939 0.575123 11.00000 -1.20000 AFIX 0 C22 1 0.178224 0.544473 0.542118 11.00000 0.03533 0.01956 = 0.02951 0.00055 0.00169 0.00599 C23 1 0.190172 0.448504 0.522940 11.00000 0.02746 0.02099 = 0.02890 0.00056 -0.00102 0.00638 AFIX 43 H23 2 0.126252 0.452393 0.509755 11.00000 -1.20000 AFIX 0 C24 1 0.288902 0.349386 0.522149 11.00000 0.03093 0.03279 = 0.01503 -0.00235 0.00155 0.00104 C25 1 0.065514 0.648680 0.541993 11.00000 0.05284 0.05133 = 0.03748 -0.00552 -0.00306 0.03156 AFIX 137 H25A 2 -0.022635 0.602322 0.540687 11.00000 -1.50000 H25B 2 0.077337 0.709984 0.527837 11.00000 -1.50000 H25C 2 0.068522 0.701523 0.557374 11.00000 -1.50000 AFIX 0 C26 1 0.603232 0.134406 0.609535 11.00000 0.01648 0.03721 = 0.01681 -0.00241 -0.00523 0.00489 C27 1 0.543296 0.272424 0.618061 11.00000 0.02916 0.02041 = 0.02063 0.00248 -0.00350 0.00283 AFIX 13 H27 2 0.617142 0.342481 0.617231 11.00000 -1.20000 AFIX 0 C28 1 0.479759 0.277645 0.643930 11.00000 0.05030 0.03776 = 0.01441 -0.00295 -0.00126 0.00172 AFIX 23 H28A 2 0.513099 0.201505 0.654313 11.00000 -1.20000 H28B 2 0.501230 0.364883 0.652263 11.00000 -1.20000 AFIX 0 C29 1 0.328462 0.264864 0.639226 11.00000 0.03615 0.04076 = 0.02652 -0.00184 0.00199 0.00274 AFIX 23 H29A 2 0.274757 0.303917 0.653020 11.00000 -1.20000 H29B 2 0.301529 0.168621 0.636738 11.00000 -1.20000 AFIX 0 C30 1 0.310599 0.348497 0.615324 11.00000 0.03419 0.03452 = 0.02748 0.00094 0.00780 0.00798 AFIX 23 H30A 2 0.226291 0.321989 0.606490 11.00000 -1.20000 H30B 2 0.307339 0.447311 0.618961 11.00000 -1.20000 AFIX 0 C31 1 0.507031 0.014430 0.616078 11.00000 0.02158 0.02236 = 0.04505 -0.00507 -0.00001 0.00105 C32 1 0.405752 -0.027195 0.600003 11.00000 0.02500 0.02846 = 0.06393 -0.01065 -0.00128 -0.01207 AFIX 43 H32 2 0.397198 0.015539 0.584303 11.00000 -1.20000 AFIX 0 C33 1 0.315531 -0.131700 0.606594 11.00000 0.03070 0.05471 = 0.09316 -0.02850 0.01047 -0.01660 AFIX 43 H33 2 0.244569 -0.157478 0.595590 11.00000 -1.20000 AFIX 0 C34 1 0.329962 -0.199005 0.629648 11.00000 0.03959 0.03575 = 0.13394 -0.01298 0.02100 0.00276 AFIX 43 H34 2 0.271535 -0.272215 0.634085 11.00000 -1.20000 AFIX 0 C35 1 0.428955 -0.156224 0.645112 11.00000 0.03991 0.03259 = 0.08606 0.01202 0.00943 0.00283 AFIX 43 H35 2 0.437422 -0.199272 0.660786 11.00000 -1.20000 AFIX 0 C36 1 0.519501 -0.051689 0.639160 11.00000 0.03356 0.04307 = 0.05058 0.01042 0.00263 -0.00009 AFIX 43 H36 2 0.588651 -0.025353 0.650497 11.00000 -1.20000 AFIX 0 C37 1 0.744719 0.105260 0.619787 11.00000 0.01765 0.03112 = 0.03146 0.00502 -0.00445 -0.00183 C38 1 0.816371 -0.004347 0.609899 11.00000 0.02634 0.04510 = 0.04160 0.00266 -0.00227 0.00332 AFIX 43 H38 2 0.776615 -0.057984 0.597167 11.00000 -1.20000 AFIX 0 C39 1 0.947597 -0.035934 0.618714 11.00000 0.02699 0.03808 = 0.06708 0.01196 0.00380 0.00544 AFIX 43 H39 2 0.995725 -0.110758 0.611784 11.00000 -1.20000 AFIX 0 C40 1 1.007078 0.039497 0.637132 11.00000 0.02166 0.04535 = 0.06656 0.01870 -0.01099 0.00541 AFIX 43 H40 2 1.096212 0.018559 0.642837 11.00000 -1.20000 AFIX 0 C41 1 0.933778 0.147821 0.647328 11.00000 0.04601 0.05823 = 0.06324 0.01406 -0.02877 -0.01147 AFIX 43 H41 2 0.971852 0.199038 0.660549 11.00000 -1.20000 AFIX 0 C42 1 0.803930 0.181581 0.638149 11.00000 0.03643 0.05180 = 0.04283 -0.00065 -0.01725 -0.00054 AFIX 43 H42 2 0.756787 0.257973 0.644728 11.00000 -1.20000 AFIX 0 C43 1 0.471038 0.425016 0.583497 11.00000 0.02813 0.02336 = 0.02291 0.00104 -0.00554 -0.00414 AFIX 23 H43A 2 0.564332 0.408649 0.577194 11.00000 -1.20000 H43B 2 0.471195 0.512795 0.592526 11.00000 -1.20000 AFIX 0 C44 1 0.466424 -0.193645 0.528893 11.00000 0.04307 0.04613 = 0.11202 0.01039 -0.00761 -0.01010 AFIX 23 H44A 2 0.443951 -0.126299 0.515876 11.00000 -1.20000 H44B 2 0.384016 -0.210661 0.538999 11.00000 -1.20000 AFIX 0 C45 1 0.517424 -0.323432 0.517630 11.00000 0.06973 0.06017 = 0.03909 0.00526 0.00749 -0.04331 AFIX 23 H45A 2 0.543223 -0.309411 0.500100 11.00000 -1.20000 H45B 2 0.447118 -0.395606 0.518515 11.00000 -1.20000 AFIX 0 C46 1 0.640062 -0.360814 0.532976 11.00000 0.06459 0.05153 = 0.06617 0.00949 0.01678 0.00577 AFIX 23 H46A 2 0.725197 -0.350800 0.523317 11.00000 -1.20000 H46B 2 0.633318 -0.455604 0.539122 11.00000 -1.20000 AFIX 0 C47 1 0.635072 -0.258265 0.554457 11.00000 0.11027 0.04675 = 0.06124 -0.00004 -0.01882 -0.00818 AFIX 23 H47A 2 0.579661 -0.293647 0.568355 11.00000 -1.20000 H47B 2 0.727775 -0.236895 0.560551 11.00000 -1.20000 AFIX 0 C48 1 0.995527 0.056296 0.532816 11.00000 0.02721 0.10227 = 0.05186 -0.03211 -0.00183 0.01114 AFIX 23 H48A 2 1.022107 0.104896 0.517502 11.00000 -1.20000 H48B 2 0.980104 -0.040969 0.528848 11.00000 -1.20000 AFIX 0 C49 1 1.104606 0.071738 0.552691 11.00000 0.02775 0.06399 = 0.07208 0.01297 -0.00293 -0.01842 AFIX 23 H49A 2 1.195131 0.087458 0.545127 11.00000 -1.20000 H49B 2 1.109210 -0.010750 0.563205 11.00000 -1.20000 AFIX 0 C50 1 1.059926 0.195287 0.567831 11.00000 0.04705 0.05745 = 0.04252 -0.00387 0.00617 -0.02889 AFIX 23 H50A 2 1.048552 0.171465 0.585517 11.00000 -1.20000 H50B 2 1.126411 0.270723 0.566371 11.00000 -1.20000 AFIX 0 C51 1 0.925833 0.232529 0.556208 11.00000 0.05554 0.04016 = 0.07830 -0.01684 0.00377 -0.02332 AFIX 23 H51A 2 0.859775 0.260233 0.569110 11.00000 -1.20000 H51B 2 0.937952 0.309386 0.544546 11.00000 -1.20000 AFIX 0 O6 5 0.149849 -0.310399 0.452163 11.00000 0.15437 0.04585 = 0.12143 -0.02084 -0.04386 0.01894 C52 1 0.219169 -0.261808 0.472688 11.00000 0.06442 0.06155 = 0.05532 0.00766 -0.00202 0.01284 AFIX 23 H52A 2 0.318072 -0.256428 0.469218 11.00000 -1.20000 H52B 2 0.204927 -0.322980 0.487027 11.00000 -1.20000 AFIX 0 C53 1 0.162950 -0.122540 0.478075 11.00000 0.06897 0.04505 = 0.04689 -0.00239 -0.00678 -0.01127 AFIX 23 H53A 2 0.231648 -0.063877 0.486229 11.00000 -1.20000 H53B 2 0.080556 -0.127655 0.488606 11.00000 -1.20000 AFIX 0 C54 1 0.128995 -0.071261 0.452251 11.00000 0.05591 0.03918 = 0.09638 0.01761 -0.02415 -0.01106 AFIX 23 H54A 2 0.040647 -0.022580 0.452146 11.00000 -1.20000 H54B 2 0.200834 -0.009137 0.446076 11.00000 -1.20000 AFIX 0 C55 1 0.121927 -0.198293 0.436811 11.00000 0.09983 0.05489 = 0.05700 -0.00771 -0.01507 0.01286 AFIX 23 H55A 2 0.030071 -0.207647 0.429431 11.00000 -1.20000 H55B 2 0.189486 -0.193676 0.423230 11.00000 -1.20000 AFIX 0 SAME 0.02 0.04 O6 > C55 O7 5 0.875948 0.597311 0.643675 11.00000 0.21746 0.15930 = 0.05418 -0.00416 -0.01505 0.09208 C56 1 0.771509 0.620808 0.626943 11.00000 0.06443 0.04880 = 0.07972 -0.01116 0.02176 -0.00776 AFIX 23 H56A 2 0.742137 0.717260 0.627516 11.00000 -1.20000 H56B 2 0.692134 0.561935 0.630617 11.00000 -1.20000 AFIX 0 C57 1 0.831365 0.586348 0.601836 11.00000 0.05495 0.07169 = 0.04639 0.00659 -0.00580 -0.01053 AFIX 23 H57A 2 0.764926 0.535529 0.591594 11.00000 -1.20000 H57B 2 0.858886 0.669990 0.592896 11.00000 -1.20000 AFIX 0 C58 1 0.951613 0.500604 0.607682 11.00000 0.09145 0.12399 = 0.05215 0.02055 0.00162 0.04264 AFIX 23 H58A 2 0.929152 0.402565 0.606282 11.00000 -1.20000 H58B 2 1.028511 0.521598 0.596452 11.00000 -1.20000 AFIX 0 C59 1 0.985056 0.537024 0.633390 11.00000 0.09972 0.08724 = 0.08900 0.00142 -0.03984 -0.00095 AFIX 23 H59A 2 1.009477 0.454133 0.642843 11.00000 -1.20000 H59B 2 1.063894 0.599931 0.633691 11.00000 -1.20000 AFIX 0 HKLF 5 REM 1_reint_smar_a.res in P4(3) REM wR2 = 0.1760, GooF = S = 0.972, Restrained GooF = 0.975 for all data REM R1 = 0.0690 for 7788 Fo > 4sig(Fo) and 0.0928 for all 10795 data REM 626 parameters refined using 71 restraints END WGHT 0.1117 0.0000 REM Instructions for potential hydrogen bonds HTAB O1 O2 HTAB O1 N1 HTAB O3 O2 HTAB O3 N2 HTAB C44 O1 REM Highest difference peak 0.259, deepest hole -0.265, 1-sigma level 0.056 Q1 1 0.6558 -0.0184 0.6192 11.00000 0.05 0.26 Q2 1 0.2408 0.3873 0.5523 11.00000 0.05 0.26 Q3 1 1.0539 0.5978 0.6164 11.00000 0.05 0.24 Q4 1 0.9643 0.0568 0.5702 11.00000 0.05 0.23 Q5 1 0.7258 -0.2397 0.5392 11.00000 0.05 0.23 Q6 1 1.1002 0.0607 0.5810 11.00000 0.05 0.23 Q7 1 0.6471 0.0220 0.6274 11.00000 0.05 0.23 Q8 1 0.7539 0.1991 0.5425 11.00000 0.05 0.23 Q9 1 0.5216 0.0383 0.5910 11.00000 0.05 0.22 Q10 1 0.5429 0.1324 0.5318 11.00000 0.05 0.22 Q11 1 0.5349 0.2560 0.5893 11.00000 0.05 0.22 Q12 1 0.7743 0.0606 0.4704 11.00000 0.05 0.21 Q13 1 0.5040 0.0439 0.4750 11.00000 0.05 0.20 Q14 1 0.2333 -0.0328 0.4399 11.00000 0.05 0.20 Q15 1 0.4208 0.2399 0.5210 11.00000 0.05 0.19 Q16 1 1.0201 0.6040 0.6096 11.00000 0.05 0.19 Q17 1 0.6265 -0.3881 0.5074 11.00000 0.05 0.19 Q18 1 0.6394 -0.0197 0.4848 11.00000 0.05 0.19 Q19 1 0.2333 -0.2335 0.4503 11.00000 0.05 0.19 Q20 1 0.5043 -0.0212 0.5386 11.00000 0.05 0.19 ; _shelx_res_checksum 24080 _olex2_date_sample_data_collection 2019-12-02 _olex2_date_sample_submission 2019-11-20 _olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+' _olex2_exptl_crystal_mounting_method 'The crystal was mounted on a MITIGEN holder in Paratone oil.' _olex2_submission_original_sample_id WG-03-37 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.705 _oxdiff_exptl_absorpt_empirical_full_min 0.559 _oxdiff_twin_integration_method simultaneous _oxdiff_twin_items 2 loop_ _twin_individual_id _twin_individual_mass_fraction_refined _oxdiff_twin_reflns_isolated _oxdiff_twin_reflns_overlapped _twin_individual_twin_lattice_type _twin_individual_twin_matrix_11 _twin_individual_twin_matrix_12 _twin_individual_twin_matrix_13 _twin_individual_twin_matrix_21 _twin_individual_twin_matrix_22 _twin_individual_twin_matrix_23 _twin_individual_twin_matrix_31 _twin_individual_twin_matrix_32 _twin_individual_twin_matrix_33 1 0.500(3) 880 82908 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000 1.0000 2 0.500(3) 709 82908 nmt 0.9994 0.0008 -0.0002 -0.0006 -1.0004 0.0009 -0.0087 -0.0532 -1.0005 _twin_special_details ; Component 2 rotated by -179.4464\% around [1.00 -0.00 -0.00] (reciprocal) or [1.00 -0.00 -0.00] (direct) ; _vrf_PLAT340_1 ; PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01288 Ang. RESPONSE: relatively poor, weak and twinned data ;