#------------------------------------------------------------------------------ #$Date: 2019-12-19 03:54:56 +0200 (Thu, 19 Dec 2019) $ #$Revision: 245361 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125669.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7125669 loop_ _publ_author_name 'Gerken, James B.' 'Stamoulis, Alexios G.' 'Suh, Sung-Eun' 'Fischer, Nicholas Darren' 'Kim, Yeon Jung' 'Guzei, Ilia' 'Stahl, Shannon S.' _publ_section_title ; Efficient Electrochemical Synthesis of Robust, Densely Functionalized Water Soluble Quinones ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/C9CC08878D _journal_year 2020 _chemical_formula_moiety '0.25(C72 H168 Na16 O88 S32)' _chemical_formula_sum 'C18 H42 Na4 O22 S8' _chemical_formula_weight 958.95 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2019-07-11 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-09-04 deposited with the CCDC. 2019-12-18 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 108.517(8) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 35.431(11) _cell_length_b 5.4941(16) _cell_length_c 20.150(8) _cell_measurement_reflns_used 9980 _cell_measurement_temperature 100 _cell_measurement_theta_max 28.363 _cell_measurement_theta_min 2.425 _cell_volume 3719(2) _computing_cell_refinement 'SAINT+ Ver. 2018.1-0. (Bruker-AXS, 2018)' _computing_data_collection 'APEX3 Ver. 2018.1-0. (Bruker-AXS, 2018)' _computing_data_reduction 'SAINT+ Ver. 2018.1-0. (Bruker-AXS, 2018)' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material 'OLEX2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2015b)' _computing_structure_solution 'XT (Sheldrick, 2015a)' _diffrn_ambient_temperature 100.0 _diffrn_detector 'charge-coupled device (CCD) area detector' _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type 'Bruker APEX II' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker APEX II Quazar' _diffrn_measurement_method '0.5\% \w and 0.5\% \f scans' _diffrn_radiation_collimation 'focusing mirrors' _diffrn_radiation_detector 'Bruker APEX II' _diffrn_radiation_monochromator 'mirror optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_av_unetI/netI 0.0223 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 46 _diffrn_reflns_limit_h_min -46 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 30138 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 28.421 _diffrn_reflns_theta_min 1.212 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_type 'Incoatec I\ms' _exptl_absorpt_coefficient_mu 0.610 _exptl_absorpt_correction_T_max 0.9412 _exptl_absorpt_correction_T_min 0.9021 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.713 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1992 _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.453 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.060 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 271 _refine_ls_number_reflns 4670 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.060 _refine_ls_R_factor_all 0.0275 _refine_ls_R_factor_gt 0.0237 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0247P)^2^+5.6582P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0599 _refine_ls_wR_factor_ref 0.0619 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4231 _reflns_number_total 4670 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc08878d2.cif _cod_data_source_block stahl253 _cod_database_code 7125669 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.994 _shelx_estimated_absorpt_t_min 0.936 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H,H) groups 2.a Secondary CH2 refined with riding coordinates: C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C7(H7A,H7B), C8(H8C,H8D), C9(H9C,H9D) ; _shelx_res_file ; TITL stahl253_a.res in C2/c stahl253.res created by SHELXL-2018/3 at 15:57:39 on 11-Jul-2019 REM Old TITL stahl253 in C2/c REM SHELXT solution in C2/c REM R1 0.058, Rweak 0.001, Alpha 0.022, Orientation as input REM Formula found by SHELXT: C9 O11 Na2 S4 CELL 0.71073 35.4309 5.4941 20.1501 90 108.517 90 ZERR 4 0.0105 0.0016 0.0077 0 0.008 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H Na O S UNIT 72 168 16 88 32 EQIV $1 -0.5+X,-1.5+Y,+Z EQIV $2 0.5-X,1.5+Y,0.5-Z EQIV $3 -X,-Y,1-Z EQIV $4 0.5-X,1.5-Y,1-Z EQIV $5 0.5-X,0.5-Y,1-Z EQIV $6 0.5+X,1.5+Y,+Z EQIV $7 0.5-X,0.5+Y,0.5-Z L.S. 12 PLAN 5 SIZE 0.01 0.08 0.11 TEMP -173.15 HTAB O8 O6_$1 HTAB O8 O9_$3 HTAB O9 O5_$4 HTAB O9 O6_$5 HTAB O10 O2_$6 HTAB O10 O8_$4 HTAB O11 O1_$7 HTAB O11 O3_$2 HTAB O4 S3 CONN 5 Na2 BOND $H LIST 4 more -1 conf fmap 2 ACTA 50 REM REM REM WGHT 0.024700 5.658200 FVAR 0.05640 S1 5 0.067162 0.349223 0.330525 11.00000 0.00765 0.00580 = 0.00786 -0.00010 0.00278 -0.00007 S2 5 0.188500 0.895482 0.351795 11.00000 0.00785 0.01124 = 0.00864 0.00165 0.00143 -0.00035 S3 5 0.256211 0.471508 0.365892 11.00000 0.00904 0.00928 = 0.00950 -0.00194 0.00392 -0.00213 S4 5 0.371547 1.170197 0.375871 11.00000 0.00730 0.00747 = 0.00797 -0.00053 0.00282 -0.00110 NA1 3 0.018687 -0.129901 0.389197 11.00000 0.01029 0.00854 = 0.01089 -0.00041 0.00456 0.00010 NA2 3 0.424371 1.659458 0.329565 11.00000 0.01039 0.00970 = 0.01102 0.00008 0.00427 -0.00053 O1 4 0.072850 0.398532 0.262829 11.00000 0.01218 0.00900 = 0.00834 0.00043 0.00358 -0.00027 O2 4 0.040672 0.526077 0.347038 11.00000 0.01069 0.00828 = 0.01591 -0.00162 0.00644 0.00101 O3 4 0.054000 0.099160 0.335034 11.00000 0.01418 0.00730 = 0.01296 -0.00012 0.00622 -0.00148 O4 4 0.306876 0.393624 0.512845 11.00000 0.01356 0.01608 = 0.01118 -0.00059 0.00297 0.00718 O5 4 0.364908 1.260761 0.439460 11.00000 0.01225 0.01318 = 0.00972 -0.00260 0.00467 -0.00117 O6 4 0.403183 0.983986 0.391614 11.00000 0.00851 0.01022 = 0.01555 -0.00119 0.00350 0.00054 O7 4 0.378427 1.364080 0.331921 11.00000 0.01401 0.01082 = 0.01274 0.00186 0.00499 -0.00397 O8 4 -0.024642 -0.239804 0.456171 11.00000 0.01160 0.01139 = 0.01244 -0.00193 0.00355 -0.00171 O9 4 0.072056 -0.113468 0.504090 11.00000 0.01189 0.01218 = 0.01500 0.00102 0.00207 -0.00066 O10 4 0.487959 1.770019 0.400039 11.00000 0.01200 0.01213 = 0.01095 -0.00134 0.00427 -0.00240 O11 4 0.459811 1.353624 0.291999 11.00000 0.01485 0.00859 = 0.01005 -0.00077 0.00386 -0.00097 C1 1 0.113941 0.374981 0.395822 11.00000 0.00928 0.01415 = 0.00937 0.00252 0.00158 -0.00097 AFIX 23 H1A 2 0.110381 0.347245 0.442015 11.00000 -1.20000 H1B 2 0.131547 0.244753 0.388583 11.00000 -1.20000 AFIX 0 C2 1 0.134667 0.619952 0.397480 11.00000 0.01044 0.01554 = 0.00975 -0.00195 0.00329 -0.00379 AFIX 23 H2A 2 0.114866 0.752362 0.390951 11.00000 -1.20000 H2B 2 0.154984 0.642068 0.443897 11.00000 -1.20000 AFIX 0 C3 1 0.154621 0.638361 0.340705 11.00000 0.00837 0.01361 = 0.01061 -0.00145 0.00303 -0.00281 AFIX 23 H3A 2 0.133734 0.652301 0.294593 11.00000 -1.20000 H3B 2 0.169582 0.486295 0.340543 11.00000 -1.20000 AFIX 0 C4 1 0.223538 0.815570 0.433906 11.00000 0.00759 0.00953 = 0.00796 0.00097 0.00187 -0.00194 C5 1 0.252029 0.632904 0.439586 11.00000 0.00793 0.00902 = 0.00886 -0.00169 0.00350 -0.00275 C6 1 0.278353 0.566542 0.505458 11.00000 0.00647 0.00881 = 0.01220 0.00045 0.00307 -0.00019 C7 1 0.276235 0.704366 0.322090 11.00000 0.00980 0.01294 = 0.00955 0.00090 0.00314 -0.00240 AFIX 23 H7A 2 0.281833 0.629582 0.281501 11.00000 -1.20000 H7B 2 0.255683 0.831105 0.303870 11.00000 -1.20000 AFIX 0 C8 1 0.314097 0.825853 0.368451 11.00000 0.00969 0.01063 = 0.01122 0.00007 0.00308 -0.00287 AFIX 23 H8C 2 0.335339 0.702573 0.385754 11.00000 -1.20000 H8D 2 0.309059 0.901884 0.409382 11.00000 -1.20000 AFIX 0 C9 1 0.327338 1.019262 0.326281 11.00000 0.00903 0.01142 = 0.00904 -0.00040 0.00226 -0.00176 AFIX 23 H9C 2 0.305808 1.140789 0.309024 11.00000 -1.20000 H9D 2 0.331788 0.941640 0.285052 11.00000 -1.20000 AFIX 0 H10A 2 0.500987 1.849444 0.381980 11.00000 0.02397 H11A 2 0.460584 1.415811 0.255787 11.00000 0.02406 H8A 2 -0.038182 -0.129529 0.463822 11.00000 0.02987 H8B 2 -0.040982 -0.337070 0.435881 11.00000 0.03573 H4 2 0.308418 0.359320 0.472864 11.00000 0.02556 H11B 2 0.451136 1.217541 0.281726 11.00000 0.03129 H10B 2 0.496131 1.794006 0.439559 11.00000 0.03441 H9A 2 0.079809 -0.234552 0.527950 11.00000 0.03210 H9B 2 0.091899 -0.031796 0.511638 11.00000 0.04419 HKLF 4 REM stahl253_a.res in C2/c REM wR2 = 0.061943, GooF = S = 1.06020, Restrained GooF = 1.06020 for all data REM R1 = 0.023746 for 4231 Fo > 4sig(Fo) and 0.027533 for all 4670 data REM 271 parameters refined using 0 restraints END WGHT 0.0247 5.6582 REM Highest difference peak 0.453, deepest hole -0.382, 1-sigma level 0.060 Q1 1 0.1450 0.6387 0.3691 11.00000 0.05 0.45 Q2 1 0.3494 1.0859 0.3506 11.00000 0.05 0.45 Q3 1 0.3209 0.9243 0.3478 11.00000 0.05 0.44 Q4 1 0.0910 0.3697 0.3658 11.00000 0.05 0.43 Q5 1 0.2215 0.8545 0.4652 11.00000 0.05 0.42 ; _shelx_res_checksum 34588 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn S1 S 0.06716(2) 0.34922(6) 0.33053(2) 0.00703(7) Uani 1 1 d . S2 S 0.18850(2) 0.89548(6) 0.35179(2) 0.00952(7) Uani 1 1 d . S3 S 0.25621(2) 0.47151(6) 0.36589(2) 0.00905(7) Uani 1 1 d . S4 S 0.37155(2) 1.17020(6) 0.37587(2) 0.00749(7) Uani 1 1 d . Na1 Na 0.01869(2) -0.12990(10) 0.38920(3) 0.00963(11) Uani 1 1 d . Na2 Na 0.42437(2) 1.65946(10) 0.32956(3) 0.01017(11) Uani 1 1 d . O1 O 0.07285(3) 0.39853(18) 0.26283(5) 0.00977(19) Uani 1 1 d . O2 O 0.04067(3) 0.52608(18) 0.34704(5) 0.01111(19) Uani 1 1 d . O3 O 0.05400(3) 0.09916(18) 0.33503(5) 0.01103(19) Uani 1 1 d . O4 O 0.30688(3) 0.39362(19) 0.51284(5) 0.0138(2) Uani 1 1 d . O5 O 0.36491(3) 1.26076(18) 0.43946(5) 0.01144(19) Uani 1 1 d . O6 O 0.40318(3) 0.98399(18) 0.39161(5) 0.01150(19) Uani 1 1 d . O7 O 0.37843(3) 1.36408(18) 0.33192(5) 0.0123(2) Uani 1 1 d . O8 O -0.02464(3) -0.2398(2) 0.45617(5) 0.0119(2) Uani 1 1 d . O9 O 0.07206(3) -0.1135(2) 0.50409(5) 0.0135(2) Uani 1 1 d . O10 O 0.48796(3) 1.77002(19) 0.40004(5) 0.01154(19) Uani 1 1 d . O11 O 0.45981(3) 1.35362(19) 0.29200(5) 0.01118(19) Uani 1 1 d . C1 C 0.11394(4) 0.3750(3) 0.39582(7) 0.0113(3) Uani 1 1 d . H1A H 0.110381 0.347245 0.442015 0.014 Uiso 1 1 calc R H1B H 0.131547 0.244753 0.388583 0.014 Uiso 1 1 calc R C2 C 0.13467(4) 0.6200(3) 0.39748(7) 0.0119(3) Uani 1 1 d . H2A H 0.114866 0.752362 0.390951 0.014 Uiso 1 1 calc R H2B H 0.154984 0.642068 0.443897 0.014 Uiso 1 1 calc R C3 C 0.15462(4) 0.6384(3) 0.34070(7) 0.0109(3) Uani 1 1 d . H3A H 0.133734 0.652301 0.294593 0.013 Uiso 1 1 calc R H3B H 0.169582 0.486295 0.340543 0.013 Uiso 1 1 calc R C4 C 0.22354(4) 0.8156(2) 0.43391(6) 0.0085(2) Uani 1 1 d . C5 C 0.25203(4) 0.6329(2) 0.43959(7) 0.0084(2) Uani 1 1 d . C6 C 0.27835(4) 0.5665(2) 0.50546(7) 0.0091(2) Uani 1 1 d . C7 C 0.27624(4) 0.7044(3) 0.32209(7) 0.0107(3) Uani 1 1 d . H7A H 0.281833 0.629582 0.281501 0.013 Uiso 1 1 calc R H7B H 0.255683 0.831105 0.303870 0.013 Uiso 1 1 calc R C8 C 0.31410(4) 0.8259(3) 0.36845(7) 0.0106(3) Uani 1 1 d . H8C H 0.335339 0.702573 0.385754 0.013 Uiso 1 1 calc R H8D H 0.309059 0.901884 0.409382 0.013 Uiso 1 1 calc R C9 C 0.32734(4) 1.0193(3) 0.32628(7) 0.0100(2) Uani 1 1 d . H9C H 0.305808 1.140789 0.309024 0.012 Uiso 1 1 calc R H9D H 0.331788 0.941640 0.285052 0.012 Uiso 1 1 calc R H10A H 0.5010(6) 1.849(4) 0.3820(11) 0.024(5) Uiso 1 1 d . H11A H 0.4606(6) 1.416(4) 0.2558(11) 0.024(5) Uiso 1 1 d . H8A H -0.0382(7) -0.130(4) 0.4638(11) 0.030(6) Uiso 1 1 d . H8B H -0.0410(7) -0.337(4) 0.4359(12) 0.036(6) Uiso 1 1 d . H4 H 0.3084(6) 0.359(4) 0.4729(11) 0.026(5) Uiso 1 1 d . H11B H 0.4511(7) 1.218(4) 0.2817(11) 0.031(6) Uiso 1 1 d . H10B H 0.4961(7) 1.794(4) 0.4396(12) 0.034(6) Uiso 1 1 d . H9A H 0.0798(6) -0.235(4) 0.5280(12) 0.032(6) Uiso 1 1 d . H9B H 0.0919(8) -0.032(5) 0.5116(12) 0.044(7) Uiso 1 1 d . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.00765(15) 0.00580(15) 0.00786(14) -0.00010(11) 0.00278(11) -0.00007(11) S2 0.00785(15) 0.01124(16) 0.00864(14) 0.00165(11) 0.00143(11) -0.00035(12) S3 0.00904(15) 0.00928(15) 0.00950(14) -0.00194(11) 0.00392(11) -0.00213(12) S4 0.00730(15) 0.00747(15) 0.00797(14) -0.00053(11) 0.00282(11) -0.00110(11) Na1 0.0103(3) 0.0085(3) 0.0109(2) -0.00041(19) 0.0046(2) 0.0001(2) Na2 0.0104(3) 0.0097(3) 0.0110(2) 0.0001(2) 0.0043(2) -0.0005(2) O1 0.0122(5) 0.0090(5) 0.0083(4) 0.0004(3) 0.0036(4) -0.0003(4) O2 0.0107(5) 0.0083(5) 0.0159(4) -0.0016(4) 0.0064(4) 0.0010(4) O3 0.0142(5) 0.0073(4) 0.0130(4) -0.0001(4) 0.0062(4) -0.0015(4) O4 0.0136(5) 0.0161(5) 0.0112(4) -0.0006(4) 0.0030(4) 0.0072(4) O5 0.0122(5) 0.0132(5) 0.0097(4) -0.0026(4) 0.0047(4) -0.0012(4) O6 0.0085(4) 0.0102(5) 0.0156(4) -0.0012(4) 0.0035(4) 0.0005(4) O7 0.0140(5) 0.0108(5) 0.0127(4) 0.0019(4) 0.0050(4) -0.0040(4) O8 0.0116(5) 0.0114(5) 0.0124(4) -0.0019(4) 0.0035(4) -0.0017(4) O9 0.0119(5) 0.0122(5) 0.0150(5) 0.0010(4) 0.0021(4) -0.0007(4) O10 0.0120(5) 0.0121(5) 0.0109(5) -0.0013(4) 0.0043(4) -0.0024(4) O11 0.0148(5) 0.0086(5) 0.0100(4) -0.0008(4) 0.0039(4) -0.0010(4) C1 0.0093(6) 0.0141(7) 0.0094(6) 0.0025(5) 0.0016(5) -0.0010(5) C2 0.0104(6) 0.0155(7) 0.0097(6) -0.0019(5) 0.0033(5) -0.0038(5) C3 0.0084(6) 0.0136(7) 0.0106(6) -0.0014(5) 0.0030(5) -0.0028(5) C4 0.0076(6) 0.0095(6) 0.0080(5) 0.0010(5) 0.0019(5) -0.0019(5) C5 0.0079(6) 0.0090(6) 0.0089(5) -0.0017(5) 0.0035(5) -0.0028(5) C6 0.0065(6) 0.0088(6) 0.0122(6) 0.0005(5) 0.0031(5) -0.0002(5) C7 0.0098(6) 0.0129(6) 0.0095(6) 0.0009(5) 0.0031(5) -0.0024(5) C8 0.0097(6) 0.0106(6) 0.0112(6) 0.0001(5) 0.0031(5) -0.0029(5) C9 0.0090(6) 0.0114(6) 0.0090(5) -0.0004(5) 0.0023(5) -0.0018(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 O1 S1 C1 107.75(6) . . O2 S1 O1 112.16(6) . . O2 S1 O3 111.71(6) . . O2 S1 C1 107.22(7) . . O3 S1 O1 111.84(6) . . O3 S1 C1 105.75(6) . . C4 S2 C3 99.25(6) . . C5 S3 C7 101.73(7) . . O5 S4 O6 111.73(6) . . O5 S4 C9 107.09(6) . . O6 S4 C9 105.76(7) . . O7 S4 O5 112.91(6) . . O7 S4 O6 112.08(6) . . O7 S4 C9 106.75(6) . . O2 Na1 Na2 129.37(3) 1_545 3_435 O2 Na1 O8 110.43(4) 1_545 . O2 Na1 O9 97.29(4) 1_545 . O2 Na1 O10 164.28(4) 1_545 3_435 O2 Na1 O11 88.62(4) 1_545 3_435 O3 Na1 Na2 101.03(4) . 3_435 O3 Na1 O2 88.58(4) . 1_545 O3 Na1 O8 160.98(4) . . O3 Na1 O9 93.15(5) . . O3 Na1 O10 82.93(4) . 3_435 O3 Na1 O11 95.64(5) . 3_435 O8 Na1 Na2 66.71(3) . 3_435 O8 Na1 O9 85.37(5) . . O8 Na1 O10 78.40(4) . 3_435 O9 Na1 Na2 131.00(3) . 3_435 O9 Na1 O10 96.36(4) . 3_435 O10 Na1 Na2 40.89(3) 3_435 3_435 O11 Na1 Na2 41.32(3) 3_435 3_435 O11 Na1 O8 84.46(5) 3_435 . O11 Na1 O9 169.52(4) 3_435 . O11 Na1 O10 79.13(4) 3_435 3_435 O1 Na2 O6 95.56(5) 4_565 1_565 O1 Na2 O7 128.89(4) 4_565 . O1 Na2 O10 93.59(4) 4_565 . O1 Na2 O11 89.03(4) 4_565 . O1 Na2 H11A 71.3(5) 4_565 . O6 Na2 H11A 162.6(5) 1_565 . O7 Na2 O6 99.80(4) . 1_565 O7 Na2 O10 136.22(4) . . O7 Na2 O11 87.51(5) . . O7 Na2 H11A 97.4(5) . . O10 Na2 O6 83.80(4) . 1_565 O10 Na2 O11 82.60(4) . . O10 Na2 H11A 85.8(4) . . O11 Na2 O6 165.89(4) . 1_565 O11 Na2 H11A 17.9(5) . . S1 O1 Na2 134.40(6) . 4_535 S1 O2 Na1 160.97(7) . 1_565 S1 O3 Na1 141.41(6) . . C6 O4 H4 108.8(14) . . S4 O6 Na2 137.38(6) . 1_545 S4 O7 Na2 141.50(6) . . Na1 O8 H8A 115.8(15) . . Na1 O8 H8B 111.5(16) . . H8A O8 H8B 103(2) . . Na1 O9 H9A 122.3(16) . . Na1 O9 H9B 123.8(17) . . H9A O9 H9B 103(2) . . Na1 O10 H10A 96.3(15) 3_565 . Na1 O10 H10B 102.2(17) 3_565 . Na2 O10 Na1 94.68(4) . 3_565 Na2 O10 H10A 116.7(15) . . Na2 O10 H10B 130.6(17) . . H10A O10 H10B 107(2) . . Na1 O11 H11A 117.0(14) 3_565 . Na1 O11 H11B 114.2(15) 3_565 . Na2 O11 Na1 97.25(4) . 3_565 Na2 O11 H11A 99.3(14) . . Na2 O11 H11B 122.8(15) . . H11A O11 H11B 106(2) . . S1 C1 H1A 108.6 . . S1 C1 H1B 108.6 . . H1A C1 H1B 107.6 . . C2 C1 S1 114.70(10) . . C2 C1 H1A 108.6 . . C2 C1 H1B 108.6 . . C1 C2 H2A 109.2 . . C1 C2 H2B 109.2 . . H2A C2 H2B 107.9 . . C3 C2 C1 112.05(11) . . C3 C2 H2A 109.2 . . C3 C2 H2B 109.2 . . S2 C3 H3A 108.8 . . S2 C3 H3B 108.8 . . C2 C3 S2 113.79(9) . . C2 C3 H3A 108.8 . . C2 C3 H3B 108.8 . . H3A C3 H3B 107.7 . . C5 C4 S2 121.60(10) . . C5 C4 C6 119.44(12) . 7_566 C6 C4 S2 118.92(10) 7_566 . C4 C5 S3 122.57(10) . . C4 C5 C6 120.47(11) . . C6 C5 S3 116.96(10) . . O4 C6 C4 117.80(12) . 7_566 O4 C6 C5 122.09(12) . . C4 C6 C5 120.09(12) 7_566 . S3 C7 H7A 108.7 . . S3 C7 H7B 108.7 . . H7A C7 H7B 107.6 . . C8 C7 S3 114.41(9) . . C8 C7 H7A 108.7 . . C8 C7 H7B 108.7 . . C7 C8 H8C 109.8 . . C7 C8 H8D 109.8 . . C7 C8 C9 109.29(11) . . H8C C8 H8D 108.3 . . C9 C8 H8C 109.8 . . C9 C8 H8D 109.8 . . S4 C9 H9C 109.1 . . S4 C9 H9D 109.1 . . C8 C9 S4 112.64(9) . . C8 C9 H9C 109.1 . . C8 C9 H9D 109.1 . . H9C C9 H9D 107.8 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 S1 O1 1.4661(10) . S1 O2 1.4609(10) . S1 O3 1.4629(11) . S1 C1 1.7644(15) . S2 C3 1.8210(15) . S2 C4 1.7796(14) . S3 C5 1.7757(14) . S3 C7 1.8212(14) . S4 O5 1.4616(10) . S4 O6 1.4757(11) . S4 O7 1.4545(10) . S4 C9 1.7736(14) . Na1 Na2 3.5479(12) 3_435 Na1 O2 2.3068(12) 1_545 Na1 O3 2.2820(11) . Na1 O8 2.4204(13) . Na1 O9 2.4825(14) . Na1 O10 2.4923(13) 3_435 Na1 O11 2.3666(13) 3_435 Na2 O1 2.3060(12) 4_565 Na2 O6 2.4294(12) 1_565 Na2 O7 2.3097(12) . Na2 O10 2.3301(13) . Na2 O11 2.3615(12) . Na2 H11A 2.62(2) . O4 C6 1.3603(16) . O4 H4 0.85(2) . O8 H8A 0.82(2) . O8 H8B 0.80(3) . O9 H9A 0.82(2) . O9 H9B 0.81(3) . O10 H10A 0.80(2) . O10 H10B 0.77(2) . O11 H11A 0.81(2) . O11 H11B 0.81(2) . C1 H1A 0.9900 . C1 H1B 0.9900 . C1 C2 1.5285(19) . C2 H2A 0.9900 . C2 H2B 0.9900 . C2 C3 1.5273(18) . C3 H3A 0.9900 . C3 H3B 0.9900 . C4 C5 1.4021(19) . C4 C6 1.4031(18) 7_566 C5 C6 1.4065(18) . C7 H7A 0.9900 . C7 H7B 0.9900 . C7 C8 1.5237(19) . C8 H8C 0.9900 . C8 H8D 0.9900 . C8 C9 1.5246(18) . C9 H9C 0.9900 . C9 H9D 0.9900 . 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 O10 H10A O2 0.80(2) 2.01(2) 2.8062(15) 172(2) 3_565 yes O11 H11A O3 0.81(2) 2.01(2) 2.7957(16) 163(2) 4_565 yes O8 H8A O9 0.82(2) 2.03(2) 2.8434(16) 171(2) 5_556 yes O8 H8B O6 0.80(3) 2.13(3) 2.9020(16) 161(2) 3_435 yes O4 H4 S3 0.85(2) 2.43(2) 2.9660(14) 121.8(17) . yes O11 H11B O1 0.81(2) 2.03(2) 2.8283(16) 169(2) 4 yes O10 H10B O8 0.77(2) 2.04(2) 2.7784(18) 160(2) 7_566 yes O9 H9A O6 0.82(2) 2.06(2) 2.8564(16) 165(2) 7_556 yes O9 H9B O5 0.81(3) 2.14(3) 2.9023(16) 158(2) 7_566 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_4 S1 C1 C2 C3 -78.94(13) . . S2 C4 C5 S3 1.29(16) . . S2 C4 C5 C6 -177.45(10) . . S3 C5 C6 O4 2.52(17) . . S3 C5 C6 C4 -179.29(10) . 7_566 S3 C7 C8 C9 -178.96(9) . . O1 S1 O2 Na1 -89.4(2) . 1_565 O1 S1 O3 Na1 -152.67(9) . . O1 S1 C1 C2 56.56(11) . . O2 S1 O1 Na2 -138.31(8) . 4_535 O2 S1 O3 Na1 -26.02(12) . . O2 S1 C1 C2 -64.36(11) . . O3 S1 O1 Na2 -11.90(10) . 4_535 O3 S1 O2 Na1 144.10(18) . 1_565 O3 S1 C1 C2 176.30(9) . . O5 S4 O6 Na2 159.89(8) . 1_545 O5 S4 O7 Na2 67.97(11) . . O5 S4 C9 C8 -53.23(11) . . O6 S4 O7 Na2 -59.27(11) . . O6 S4 C9 C8 66.07(11) . . O7 S4 O6 Na2 -72.24(10) . 1_545 O7 S4 C9 C8 -174.41(9) . . C1 S1 O1 Na2 103.91(9) . 4_535 C1 S1 O2 Na1 28.7(2) . 1_565 C1 S1 O3 Na1 90.31(11) . . C1 C2 C3 S2 -167.42(9) . . C3 S2 C4 C5 76.23(12) . . C3 S2 C4 C6 -101.71(12) . 7_566 C4 S2 C3 C2 61.90(11) . . C4 C5 C6 O4 -178.67(12) . . C4 C5 C6 C4 -0.5(2) . 7_566 C5 S3 C7 C8 53.97(11) . . C6 C4 C5 S3 179.22(10) 7_566 . C6 C4 C5 C6 0.5(2) 7_566 . C7 S3 C5 C4 70.85(12) . . C7 S3 C5 C6 -110.36(11) . . C7 C8 C9 S4 -179.65(9) . . C9 S4 O6 Na2 43.71(10) . 1_545 C9 S4 O7 Na2 -174.62(9) . .