#------------------------------------------------------------------------------
#$Date: 2019-12-19 03:54:56 +0200 (Thu, 19 Dec 2019) $
#$Revision: 245361 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125670.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_7125670
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(C56 H88 Na16 O68 S32)'
_chemical_formula_sum 'C14 H22 Na4 O17 S8'
_chemical_formula_weight 810.75
_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 2017-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2019-09-04 deposited with the CCDC. 2019-12-18 downloaded from the CCDC.
;
_cell_angle_alpha 90
_cell_angle_beta 96.888(13)
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 19.151(5)
_cell_length_b 5.1130(16)
_cell_length_c 29.210(7)
_cell_measurement_reflns_used 9956
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 30.5104
_cell_measurement_theta_min 2.4169
_cell_volume 2839.6(13)
_computing_cell_refinement 'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_collection 'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction 'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_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 100.01
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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_radiation_xray_symbol K-L~3~
_diffrn_reflns_av_R_equivalents 0.0364
_diffrn_reflns_av_unetI/netI 0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max 23
_diffrn_reflns_limit_h_min -23
_diffrn_reflns_limit_k_max 6
_diffrn_reflns_limit_k_min -6
_diffrn_reflns_limit_l_max 36
_diffrn_reflns_limit_l_min -36
_diffrn_reflns_number 30410
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full 25.000
_diffrn_reflns_theta_max 25.999
_diffrn_reflns_theta_min 1.404
_diffrn_source 'microfocus sealed X-ray tube'
_diffrn_source_type 'Incoatec I\ms'
_exptl_absorpt_coefficient_mu 0.767
_exptl_absorpt_correction_T_max 0.9848
_exptl_absorpt_correction_T_min 0.9325
_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 red
_exptl_crystal_colour_primary red
_exptl_crystal_density_diffrn 1.896
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description plate
_exptl_crystal_F_000 1656
_exptl_crystal_size_max 0.118
_exptl_crystal_size_mid 0.043
_exptl_crystal_size_min 0.036
_refine_diff_density_max 0.348
_refine_diff_density_min -0.360
_refine_diff_density_rms 0.071
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.076
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 205
_refine_ls_number_reflns 2785
_refine_ls_number_restraints 1
_refine_ls_restrained_S_all 1.076
_refine_ls_R_factor_all 0.0344
_refine_ls_R_factor_gt 0.0289
_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^)+(0.0373P)^2^+5.2934P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0723
_refine_ls_wR_factor_ref 0.0746
_reflns_Friedel_coverage 0.000
_reflns_number_gt 2438
_reflns_number_total 2785
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file c9cc08878d2.cif
_cod_data_source_block stahl230b
_cod_database_code 7125670
_shelx_shelxl_version_number 2016/6
_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 0.973
_shelx_estimated_absorpt_t_min 0.915
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H,H) groups
At 1.5 times of:
All O(H,H) groups
2. Restrained distances
O2-H2B \\sim O2-H2A
with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
C1(H1A,H1B), C2(H2C,H2D), C6(H6A,H6B), C7(H7A,H7B)
;
_shelx_res_file
;
TITL STAHL230B_A.RES IN C2/C
stahl230b.res
created by SHELXL-2016/6 at 11:29:47 on 11-Apr-2017
REM OLD TITL STAHL230B IN C2/C
REM SHELXT SOLUTION IN C2/C
REM R1 0.076, RWEAK 0.001, ALPHA 0.019, ORIENTATION AS INPUT
REM FORMULA FOUND BY SHELXT: C14 O17 NA4 S8
REM ============ UPDATED INSTRUCTIONS ============
REM ================================================
REM FCF_FILTER (MSL, UW-MADISON) INSERTED 16 OMIT INSTRUCTIONS
REM FOR OUTLIER REFLECTIONS WITH THE CUTOFF VALUE OF 4.65602.
REM
REM
REM
REM The weighting scheme has been updated.
CELL 0.71073 19.1509 5.113 29.2104 90 96.888 90
ZERR 4 0.0049 0.0016 0.007 0 0.013 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H Na O S
UNIT 56 88 16 68 32
EQIV $1 +X,1+Y,+Z
SADI O2 H2b O2 H2a
L.S. 12
PLAN 5
SIZE 0.036 0.043 0.118
TEMP -173.14
HTAB O2 O4_$1
CONN 6 Na2
CONN 4 O1
FREE S1 Na2
BOND $H
CONF
LIST 4
MORE -1
fmap 2 53
acta 50
OMIT 0 52
OMIT -6 0 24
OMIT 18 0 6
OMIT 9 3 3
OMIT 0 2 0
OMIT 12 0 0
OMIT -21 3 6
OMIT 5 1 7
OMIT 15 3 18
OMIT 24 0 8
OMIT 3 3 27
OMIT -3 1 14
OMIT 2 0 10
OMIT -7 1 1
OMIT -9 3 9
OMIT -2 2 9
OMIT -8 0 2
REM
REM
REM
WGHT 0.037300 5.293400
FVAR 0.16559
S1 5 0.556675 0.341129 0.638577 11.00000 0.01196 0.01212 =
0.01051 -0.00069 0.00216 0.00008
S2 5 0.594276 0.021684 0.504729 11.00000 0.01519 0.02870 =
0.01184 -0.00457 0.00207 -0.00219
S3 5 0.619196 0.452067 0.429839 11.00000 0.01435 0.02973 =
0.01000 -0.00167 0.00055 0.00740
S4 5 0.649251 0.133294 0.295561 11.00000 0.00998 0.01099 =
0.00963 -0.00037 0.00093 0.00056
NA1 3 0.527159 0.917969 0.701494 11.00000 0.01432 0.01409 =
0.01286 0.00043 0.00263 0.00090
NA2 3 0.683284 0.417442 0.723009 11.00000 0.01372 0.01443 =
0.01354 -0.00002 0.00131 -0.00082
O1 4 0.500000 1.266386 0.750000 10.50000 0.01121 0.01291 =
0.01492 0.00000 -0.00077 0.00000
O2 4 0.705221 0.750747 0.672337 11.00000 0.01301 0.01731 =
0.02165 0.00345 -0.00120 -0.00036
H2A 2 0.738942 0.843514 0.681720 11.00000 -1.50000
H2B 2 0.671824 0.851150 0.664377 11.00000 -1.50000
O3 4 0.555018 0.615247 0.650978 11.00000 0.02186 0.01326 =
0.01876 -0.00304 0.00551 -0.00031
O4 4 0.612279 0.197316 0.667437 11.00000 0.01361 0.01692 =
0.01262 -0.00053 -0.00044 0.00006
O5 4 0.489547 0.209069 0.638668 11.00000 0.01046 0.01854 =
0.01532 0.00196 0.00155 -0.00017
O6 4 0.767525 0.645830 0.444351 11.00000 0.02254 0.02299 =
0.01865 0.00210 0.00256 0.00030
O7 4 0.709628 0.286716 0.284461 11.00000 0.01095 0.01428 =
0.01437 0.00103 0.00341 0.00031
O8 4 0.653231 -0.139599 0.282449 11.00000 0.01569 0.01229 =
0.01602 -0.00216 0.00069 0.00213
O9 4 0.582536 0.254026 0.275594 11.00000 0.01082 0.01453 =
0.01283 -0.00090 -0.00122 0.00247
C1 1 0.578734 0.328343 0.581135 11.00000 0.01796 0.01783 =
0.00935 0.00190 0.00437 -0.00047
AFIX 23
H1A 2 0.542287 0.420453 0.560216 11.00000 -1.20000
H1B 2 0.624213 0.418024 0.579611 11.00000 -1.20000
AFIX 0
C2 1 0.584095 0.046065 0.565569 11.00000 0.01905 0.01779 =
0.01052 -0.00172 0.00452 -0.00019
AFIX 23
H2C 2 0.541171 -0.049549 0.571574 11.00000 -1.20000
H2D 2 0.624846 -0.038140 0.583870 11.00000 -1.20000
AFIX 0
C3 1 0.678438 0.158225 0.501707 11.00000 0.01380 0.02154 =
0.01345 -0.00567 0.00226 0.00128
C4 1 0.689591 0.328080 0.467864 11.00000 0.01434 0.02211 =
0.01215 -0.00437 0.00032 0.00493
C5 1 0.760943 0.450874 0.467144 11.00000 0.01678 0.02200 =
0.01054 -0.00357 0.00190 0.00192
C6 1 0.650166 0.426436 0.373743 11.00000 0.01666 0.01610 =
0.00875 -0.00030 0.00110 0.00192
AFIX 23
H6A 2 0.619405 0.532547 0.351254 11.00000 -1.20000
H6B 2 0.698317 0.499303 0.375594 11.00000 -1.20000
AFIX 0
C7 1 0.650969 0.144275 0.356478 11.00000 0.01413 0.01428 =
0.00759 0.00080 0.00091 0.00128
AFIX 23
H7A 2 0.609620 0.049827 0.365515 11.00000 -1.20000
H7B 2 0.693854 0.055224 0.371100 11.00000 -1.20000
AFIX 0
H1 2 0.469821 1.360405 0.738483 11.00000 0.03346
HKLF 4
REM STAHL230B_A.RES IN C2/C
REM R1 = 0.0289 for 2438 Fo > 4sig(Fo) and 0.0344 for all 2785 data
REM 205 parameters refined using 1 restraints
END
WGHT 0.0376 5.7312
REM Highest difference peak 0.348, deepest hole -0.360, 1-sigma level 0.071
Q1 1 0.5568 0.5173 0.6424 11.00000 0.05 0.34
Q2 1 0.5588 0.6389 0.6415 11.00000 0.05 0.32
Q3 1 0.5644 0.3391 0.6016 11.00000 0.05 0.31
Q4 1 0.7332 0.6555 0.4251 11.00000 0.05 0.29
Q5 1 0.6449 0.1200 0.5032 11.00000 0.05 0.28
;
_shelx_res_checksum 27828
_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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
S1 S 0.55668(2) 0.34113(9) 0.63858(2) 0.01146(12) Uani 1 1 d . . .
S2 S 0.59428(3) 0.02168(11) 0.50473(2) 0.01854(13) Uani 1 1 d . . .
S3 S 0.61920(3) 0.45207(11) 0.42984(2) 0.01810(13) Uani 1 1 d . . .
S4 S 0.64925(2) 0.13329(9) 0.29556(2) 0.01022(12) Uani 1 1 d . . .
Na1 Na 0.52716(4) 0.91797(15) 0.70149(3) 0.01367(18) Uani 1 1 d . . .
Na2 Na 0.68328(4) 0.41744(15) 0.72301(3) 0.01392(18) Uani 1 1 d . . .
O1 O 0.500000 1.2664(4) 0.750000 0.0132(4) Uani 1 2 d S T P
O2 O 0.70522(7) 0.7507(3) 0.67234(5) 0.0176(3) Uani 1 1 d D . .
H2A H 0.7389(12) 0.844(5) 0.6817(9) 0.026 Uiso 1 1 d DR . .
H2B H 0.6718(11) 0.851(5) 0.6644(9) 0.026 Uiso 1 1 d DR . .
O3 O 0.55502(8) 0.6152(3) 0.65098(5) 0.0177(3) Uani 1 1 d . . .
O4 O 0.61228(7) 0.1973(3) 0.66744(4) 0.0145(3) Uani 1 1 d . . .
O5 O 0.48955(7) 0.2091(3) 0.63867(5) 0.0148(3) Uani 1 1 d . . .
O6 O 0.76752(8) 0.6458(3) 0.44435(5) 0.0214(3) Uani 1 1 d . . .
O7 O 0.70963(7) 0.2867(3) 0.28446(5) 0.0130(3) Uani 1 1 d . . .
O8 O 0.65323(7) -0.1396(3) 0.28245(5) 0.0148(3) Uani 1 1 d . . .
O9 O 0.58254(7) 0.2540(3) 0.27559(4) 0.0129(3) Uani 1 1 d . . .
C1 C 0.57873(10) 0.3283(4) 0.58113(6) 0.0148(4) Uani 1 1 d . . .
H1A H 0.542287 0.420453 0.560216 0.018 Uiso 1 1 calc R . .
H1B H 0.624213 0.418024 0.579611 0.018 Uiso 1 1 calc R . .
C2 C 0.58410(11) 0.0461(4) 0.56557(7) 0.0156(4) Uani 1 1 d . . .
H2C H 0.541171 -0.049549 0.571574 0.019 Uiso 1 1 calc R . .
H2D H 0.624846 -0.038140 0.583870 0.019 Uiso 1 1 calc R . .
C3 C 0.67844(10) 0.1582(4) 0.50171(7) 0.0162(4) Uani 1 1 d . . .
C4 C 0.68959(10) 0.3281(4) 0.46786(7) 0.0163(4) Uani 1 1 d . . .
C5 C 0.76094(10) 0.4509(4) 0.46714(7) 0.0164(4) Uani 1 1 d . . .
C6 C 0.65017(10) 0.4264(4) 0.37374(6) 0.0139(4) Uani 1 1 d . . .
H6A H 0.619405 0.532547 0.351254 0.017 Uiso 1 1 calc R . .
H6B H 0.698317 0.499303 0.375594 0.017 Uiso 1 1 calc R . .
C7 C 0.65097(10) 0.1443(4) 0.35648(6) 0.0120(4) Uani 1 1 d . . .
H7A H 0.609620 0.049827 0.365515 0.014 Uiso 1 1 calc R . .
H7B H 0.693854 0.055224 0.371100 0.014 Uiso 1 1 calc R . .
H1 H 0.4698(13) 1.360(6) 0.7385(9) 0.033(8) 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 0.0120(2) 0.0121(2) 0.0105(2) -0.00069(17) 0.00216(17) 0.00008(18)
S2 0.0152(3) 0.0287(3) 0.0118(2) -0.0046(2) 0.00207(19) -0.0022(2)
S3 0.0144(3) 0.0297(3) 0.0100(2) -0.0017(2) 0.00055(18) 0.0074(2)
S4 0.0100(2) 0.0110(2) 0.0096(2) -0.00037(17) 0.00093(17) 0.00056(17)
Na1 0.0143(4) 0.0141(4) 0.0129(4) 0.0004(3) 0.0026(3) 0.0009(3)
Na2 0.0137(4) 0.0144(4) 0.0135(4) 0.0000(3) 0.0013(3) -0.0008(3)
O1 0.0112(10) 0.0129(10) 0.0149(10) 0.000 -0.0008(8) 0.000
O2 0.0130(7) 0.0173(8) 0.0217(8) 0.0035(6) -0.0012(6) -0.0004(6)
O3 0.0219(8) 0.0133(7) 0.0188(7) -0.0030(6) 0.0055(6) -0.0003(6)
O4 0.0136(7) 0.0169(7) 0.0126(7) -0.0005(6) -0.0004(5) 0.0001(6)
O5 0.0105(7) 0.0185(7) 0.0153(7) 0.0020(6) 0.0015(5) -0.0002(6)
O6 0.0225(8) 0.0230(8) 0.0187(7) 0.0021(6) 0.0026(6) 0.0003(6)
O7 0.0110(7) 0.0143(7) 0.0144(7) 0.0010(5) 0.0034(5) 0.0003(5)
O8 0.0157(7) 0.0123(7) 0.0160(7) -0.0022(5) 0.0007(6) 0.0021(5)
O9 0.0108(7) 0.0145(7) 0.0128(7) -0.0009(5) -0.0012(5) 0.0025(5)
C1 0.0180(10) 0.0178(10) 0.0093(9) 0.0019(8) 0.0044(7) -0.0005(8)
C2 0.0190(10) 0.0178(10) 0.0105(9) -0.0017(8) 0.0045(8) -0.0002(8)
C3 0.0138(9) 0.0215(11) 0.0134(10) -0.0057(8) 0.0023(8) 0.0013(8)
C4 0.0143(10) 0.0221(11) 0.0122(9) -0.0044(8) 0.0003(7) 0.0049(8)
C5 0.0168(10) 0.0220(11) 0.0105(9) -0.0036(8) 0.0019(8) 0.0019(8)
C6 0.0167(10) 0.0161(10) 0.0087(9) -0.0003(7) 0.0011(7) 0.0019(8)
C7 0.0141(9) 0.0143(10) 0.0076(9) 0.0008(7) 0.0009(7) 0.0013(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O3 S1 Na1 122.99(6) . 1_545
O3 S1 O4 112.07(9) . .
O3 S1 O5 113.79(9) . .
O3 S1 C1 106.62(9) . .
O4 S1 Na1 56.93(6) . 1_545
O4 S1 C1 106.51(9) . .
O5 S1 Na1 54.52(6) . 1_545
O5 S1 O4 110.25(8) . .
O5 S1 C1 107.15(9) . .
C1 S1 Na1 130.39(7) . 1_545
C3 S2 C2 103.14(9) . .
C4 S3 C6 103.63(9) . .
Na2 S4 Na2 71.06(2) 6_565 7_656
O7 S4 Na2 37.24(6) . 7_656
O7 S4 Na2 41.47(6) . 6_565
O7 S4 O9 110.95(8) . .
O7 S4 C7 106.52(9) . .
O8 S4 Na2 119.16(6) . 6_565
O8 S4 Na2 78.45(6) . 7_656
O8 S4 O7 112.86(8) . .
O8 S4 O9 111.62(8) . .
O8 S4 C7 107.43(9) . .
O9 S4 Na2 71.20(6) . 6_565
O9 S4 Na2 140.77(6) . 7_656
O9 S4 C7 107.10(8) . .
C7 S4 Na2 105.27(7) . 7_656
C7 S4 Na2 130.61(7) . 6_565
S1 Na1 Na1 132.49(2) 1_565 2_656
S1 Na1 Na2 54.61(2) 1_565 1_565
S1 Na1 Na2 112.34(3) 1_565 .
Na1 Na1 Na2 100.62(3) 2_656 1_565
Na1 Na1 Na2 100.61(3) 2_656 .
Na2 Na1 Na2 81.24(3) 1_565 .
O1 Na1 S1 83.86(5) . 1_565
O1 Na1 Na1 48.67(4) . 2_656
O1 Na1 Na2 68.48(3) . 1_565
O1 Na1 Na2 127.65(3) . .
O1 Na1 O4 90.51(5) . 1_565
O1 Na1 O5 85.64(5) . 1_565
O1 Na1 O9 81.08(5) . 6_566
O1 Na1 O9 81.34(5) . 5_666
O3 Na1 S1 91.02(5) . 1_565
O3 Na1 Na1 136.45(4) . 2_656
O3 Na1 Na2 54.56(4) . .
O3 Na1 Na2 108.49(5) . 1_565
O3 Na1 O1 174.88(6) . .
O3 Na1 O4 85.04(6) . 1_565
O3 Na1 O5 89.90(6) . 1_565
O3 Na1 O9 102.75(6) . 6_566
O3 Na1 O9 102.22(6) . 5_666
O4 Na1 S1 30.05(3) 1_565 1_565
O4 Na1 Na1 132.24(4) 1_565 2_656
O4 Na1 Na2 85.10(4) 1_565 .
O4 Na1 Na2 32.82(4) 1_565 1_565
O5 Na1 S1 29.45(4) 1_565 1_565
O5 Na1 Na1 126.05(5) 1_565 2_656
O5 Na1 Na2 82.66(4) 1_565 1_565
O5 Na1 Na2 132.67(4) 1_565 .
O5 Na1 O4 59.04(5) 1_565 1_565
O5 Na1 O9 104.07(5) 1_565 5_666
O5 Na1 O9 162.20(6) 1_565 6_566
O9 Na1 S1 136.05(5) 6_566 1_565
O9 Na1 S1 132.28(4) 5_666 1_565
O9 Na1 Na1 50.42(4) 5_666 2_656
O9 Na1 Na1 50.07(4) 6_566 2_656
O9 Na1 Na2 81.47(4) 6_566 1_565
O9 Na1 Na2 148.61(4) 5_666 1_565
O9 Na1 Na2 112.61(4) 5_666 .
O9 Na1 Na2 52.11(4) 6_566 .
O9 Na1 O4 161.97(6) 5_666 1_565
O9 Na1 O4 109.06(5) 6_566 1_565
O9 Na1 O9 85.66(6) 5_666 6_566
O2 Na2 S4 87.87(5) . 6_566
O2 Na2 O7 88.62(6) . 6_566
O2 Na2 O7 92.31(6) . 7_656
O2 Na2 O8 169.68(6) . 6_556
O4 Na2 S4 131.59(5) . 6_566
O4 Na2 O2 92.65(6) . .
O4 Na2 O7 155.86(6) . 6_566
O4 Na2 O7 99.67(6) . 7_656
O4 Na2 O8 92.82(6) . 6_556
O7 Na2 S4 128.70(5) 7_656 6_566
O7 Na2 S4 24.33(3) 6_566 6_566
O7 Na2 O7 104.37(4) 7_656 6_566
O7 Na2 O8 82.82(6) 6_566 6_556
O7 Na2 O8 95.38(6) 7_656 6_556
O8 Na2 S4 81.96(5) 6_556 6_566
Na1 O1 Na1 82.66(8) 2_656 .
Na1 O1 H1 114(2) 2_656 2_656
Na1 O1 H1 120(2) . 2_656
Na1 O1 H1 114(2) . .
Na1 O1 H1 120(2) 2_656 .
H1 O1 H1 106(4) . 2_656
Na2 O2 H2A 113.9(18) . .
Na2 O2 H2B 116.0(18) . .
H2A O2 H2B 107(3) . .
S1 O3 Na1 147.65(9) . .
S1 O4 Na1 93.01(7) . 1_545
S1 O4 Na2 119.24(8) . .
Na2 O4 Na1 111.39(6) . 1_545
S1 O5 Na1 96.02(7) . 1_545
S4 O7 Na2 120.44(8) . 7_656
S4 O7 Na2 114.20(8) . 6_565
Na2 O7 Na2 109.04(6) 7_656 6_565
S4 O8 Na2 142.71(9) . 6
S4 O9 Na1 117.43(8) . 6_565
S4 O9 Na1 118.26(8) . 5_666
Na1 O9 Na1 79.51(5) 5_666 6_565
S1 C1 H1A 109.6 . .
S1 C1 H1B 109.6 . .
H1A C1 H1B 108.1 . .
C2 C1 S1 110.42(13) . .
C2 C1 H1A 109.6 . .
C2 C1 H1B 109.6 . .
S2 C2 H2C 109.2 . .
S2 C2 H2D 109.2 . .
C1 C2 S2 112.15(14) . .
C1 C2 H2C 109.2 . .
C1 C2 H2D 109.2 . .
H2C C2 H2D 107.9 . .
C4 C3 S2 121.00(16) . .
C4 C3 C5 120.38(18) . 7_656
C5 C3 S2 117.93(16) 7_656 .
C3 C4 S3 121.13(16) . .
C3 C4 C5 120.07(18) . .
C5 C4 S3 117.96(15) . .
O6 C5 C3 121.09(19) . 7_656
O6 C5 C4 120.27(18) . .
C3 C5 C4 118.40(18) 7_656 .
S3 C6 H6A 109.1 . .
S3 C6 H6B 109.1 . .
H6A C6 H6B 107.8 . .
C7 C6 S3 112.56(13) . .
C7 C6 H6A 109.1 . .
C7 C6 H6B 109.1 . .
S4 C7 H7A 109.4 . .
S4 C7 H7B 109.4 . .
C6 C7 S4 111.13(13) . .
C6 C7 H7A 109.4 . .
C6 C7 H7B 109.4 . .
H7A C7 H7B 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 Na1 2.9373(11) 1_545
S1 O3 1.4489(15) .
S1 O4 1.4731(14) .
S1 O5 1.4524(14) .
S1 C1 1.7799(19) .
S2 C2 1.815(2) .
S2 C3 1.768(2) .
S3 C4 1.759(2) .
S3 C6 1.813(2) .
S4 Na2 3.2441(11) 6_565
S4 Na2 3.3262(12) 7_656
S4 O7 1.4654(14) .
S4 O8 1.4513(15) .
S4 O9 1.4747(14) .
S4 C7 1.7766(19) .
Na1 Na1 3.1336(16) 2_656
Na1 Na2 3.9251(13) 1_565
Na1 Na2 3.9285(13) .
Na1 O1 2.3724(18) .
Na1 O3 2.2464(16) .
Na1 O4 2.4649(16) 1_565
Na1 O5 2.4052(16) 1_565
Na1 O9 2.4437(16) 5_666
Na1 O9 2.4561(16) 6_566
Na2 O2 2.3282(17) .
Na2 O4 2.2850(16) .
Na2 O7 2.3346(16) 7_656
Na2 O7 2.3554(16) 6_566
Na2 O8 2.3672(16) 6_556
O1 H1 0.79(3) 2_656
O1 H1 0.79(3) .
O2 H2A 0.82(2) .
O2 H2B 0.83(2) .
O6 C5 1.214(3) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C1 C2 1.520(3) .
C2 H2C 0.9900 .
C2 H2D 0.9900 .
C3 C4 1.352(3) .
C3 C5 1.494(3) 7_656
C4 C5 1.506(3) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C6 C7 1.529(3) .
C7 H7A 0.9900 .
C7 H7B 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
O2 H2B O4 0.83(2) 2.11(2) 2.888(2) 155(2) 1_565
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 S2 171.93(10) . .
S2 C3 C4 S3 8.1(3) . .
S2 C3 C4 C5 177.36(14) . .
S3 C4 C5 O6 7.3(3) . .
S3 C4 C5 C3 -178.18(14) . 7_656
S3 C6 C7 S4 158.31(10) . .
Na1 S1 O3 Na1 -10.0(2) 1_545 .
Na1 S1 O4 Na2 -116.62(9) 1_545 .
Na1 S1 C1 C2 -2.02(18) 1_545 .
Na2 S4 O7 Na2 132.75(12) 7_656 6_565
Na2 S4 O7 Na2 -132.75(12) 6_565 7_656
Na2 S4 O8 Na2 -56.09(12) 7_656 6
Na2 S4 O8 Na2 4.35(15) 6_565 6
Na2 S4 O9 Na1 177.57(8) 6_565 5_666
Na2 S4 O9 Na1 84.92(7) 6_565 6_565
Na2 S4 O9 Na1 68.50(12) 7_656 6_565
Na2 S4 O9 Na1 161.15(4) 7_656 5_666
Na2 S4 C7 C6 17.20(18) 6_565 .
Na2 S4 C7 C6 95.13(13) 7_656 .
O3 S1 O4 Na1 115.92(8) . 1_545
O3 S1 O4 Na2 -0.70(12) . .
O3 S1 O5 Na1 -114.62(8) . 1_545
O3 S1 C1 C2 178.15(14) . .
O4 S1 O3 Na1 -73.95(19) . .
O4 S1 O5 Na1 12.28(9) . 1_545
O4 S1 C1 C2 58.31(16) . .
O5 S1 O3 Na1 52.0(2) . .
O5 S1 O4 Na1 -11.93(9) . 1_545
O5 S1 O4 Na2 -128.54(9) . .
O5 S1 C1 C2 -59.67(16) . .
O7 S4 O8 Na2 -41.55(16) . 6
O7 S4 O9 Na1 -170.37(8) . 5_666
O7 S4 O9 Na1 96.98(9) . 6_565
O7 S4 C7 C6 56.38(15) . .
O8 S4 O7 Na2 -23.99(11) . 7_656
O8 S4 O7 Na2 108.76(9) . 6_565
O8 S4 O9 Na1 -29.83(11) . 6_565
O8 S4 O9 Na1 62.82(10) . 5_666
O8 S4 C7 C6 177.56(13) . .
O9 S4 O7 Na2 -17.37(10) . 6_565
O9 S4 O7 Na2 -150.12(8) . 7_656
O9 S4 O8 Na2 84.22(15) . 6
O9 S4 C7 C6 -62.40(15) . .
C1 S1 O3 Na1 169.88(16) . .
C1 S1 O4 Na1 -127.85(8) . 1_545
C1 S1 O4 Na2 115.54(10) . .
C1 S1 O5 Na1 127.80(8) . 1_545
C2 S2 C3 C4 -135.92(18) . .
C2 S2 C3 C5 53.64(17) . 7_656
C3 S2 C2 C1 67.11(16) . .
C3 C4 C5 O6 -162.31(19) . .
C3 C4 C5 C3 12.2(3) . 7_656
C4 S3 C6 C7 73.20(16) . .
C5 C3 C4 S3 178.27(15) 7_656 .
C5 C3 C4 C5 -12.4(3) 7_656 .
C6 S3 C4 C3 -135.18(17) . .
C6 S3 C4 C5 55.30(17) . .
C7 S4 O7 Na2 93.66(10) . 7_656
C7 S4 O7 Na2 -133.60(9) . 6_565
C7 S4 O8 Na2 -158.66(13) . 6
C7 S4 O9 Na1 -54.50(10) . 5_666
C7 S4 O9 Na1 -147.15(9) . 6_565