# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_201118-heodc-ox-223k-
_database_code_depnum_ccdc_archive 'CCDC 2196210'
loop_
_audit_author_name
_audit_author_address
'Biao Zhou'
;Nihon University
Japan
;
_audit_update_record             
;
2023-02-15 deposited with the CCDC.	2023-02-20 downloaded from the CCDC.
;
_audit_creation_date             2023-02-02
_audit_creation_method           
;
Olex2 1.5-dev
(compiled 2023.01.20 svn.r024a95a1 for OlexSys, GUI svn.r6444)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H5 O6 S4, C2 H2 O4, 0.5(C8 H20 N)'
_chemical_formula_sum            'C16 H17 N0.50 O10 S4'
_chemical_formula_weight         504.54
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   22.5852(5)
_cell_length_b                   12.2019(3)
_cell_length_c                   7.3075(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.150(2)
_cell_angle_gamma                90
_cell_volume                     1988.19(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21634
_cell_measurement_temperature    223
_cell_measurement_theta_max      31.3340
_cell_measurement_theta_min      1.9530
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.924
_exptl_absorpt_coefficient_mu    0.535
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1042
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            33387
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         2.740
_diffrn_ambient_temperature      223.00
_diffrn_detector_area_resol_mean 7.1429
_diffrn_detector_type            'Rigaku Saturn724+ area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50    5.00    --  -20.00  45.00   0.00  360
  2  ω   -110.00  70.00   0.50    5.00    --  -20.00  45.00  90.00  360
  3  ω   -110.00  70.00   0.50    5.00    --  -20.00  45.00 180.00  360
  4  ω   -110.00  70.00   0.50    5.00    --  -20.00  45.00 270.00  360
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4133
_reflns_number_total             4923
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         4923
_refine_ls_number_restraints     141
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0292
_refine_ls_restrained_S_all      1.007
_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/[σ²(Fo²)+(0.0446P)²+0.5021P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0806
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N2-C13
 1.55 with sigma of 0.02
 N2-C15 = N2-C17 = C17-C18
 1.54 with sigma of 0.02
 N2-C19
 1.5 with sigma of 0.02
 C13-C14
 1.56 with sigma of 0.02
 C15-C16
 1.51 with sigma of 0.02
 C19-C1A
 1.49 with sigma of 0.02
 N2-C14
 2.62 with sigma of 0.04
 N2-C16
 2.58 with sigma of 0.04
 N2-C18
 2.56 with sigma of 0.04
 N2-C1A
 2.52 with sigma of 0.04
 N2-C13 \\sim N2-C19 \\sim N2-C15 \\sim N2-C17
 with sigma of 0.02
 C13-C14 \\sim C15-C16 \\sim C17-C18 \\sim C19-C1A
 with sigma of 0.02
 C13-C15 \\sim C15-C17 \\sim C17-C19 \\sim C19-C13
 with sigma of 0.04
 C14-C16 \\sim C16-C18 \\sim C18-C1A
 with sigma of 0.08
 N2-C14 \\sim N2-C16 \\sim N2-C18 \\sim N2-C1A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
N2 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim C18 \\sim C19 \\sim
C1A: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 N2, C13, C14, C15, C16, C17, C18, C19, C1A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N2, C13, C15, C17, C19, C14, C16, C18, C1A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O7, H7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: N2(0.5) C13(0.5) H13A(0.5) H13B(0.5) C14(0.5) H14A(0.5) H14B(0.5)
 H14C(0.5) C15(0.5) H15A(0.5) H15B(0.5) C16(0.5) H16A(0.5) H16B(0.5) H16C(0.5)
 C17(0.5) H17A(0.5) H17B(0.5) C18(0.5) H18A(0.5) H18B(0.5) H18C(0.5) C19(0.5)
 H19A(0.5) H19B(0.5) C1A(0.5) H1AA(0.5) H1AB(0.5) H1AC(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C9(H9A,H9B), C13(H13A,H13B), C15(H15A,H15B), C17(H17A,H17B),
 C19(H19A,H19B)
6.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C1A(H1AA,H1AB,
 H1AC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
S2 S 0.65115(2) 0.72818(2) 0.50067(4) 0.02542(8) Uani 1 1 d . . . . .
S4 S 0.51762(2) 0.72814(2) 0.27280(4) 0.02682(8) Uani 1 1 d . . . . .
S1 S 0.65157(2) 0.96928(2) 0.50318(5) 0.02967(9) Uani 1 1 d . . . . .
S3 S 0.51848(2) 0.97032(2) 0.26977(5) 0.03212(9) Uani 1 1 d . . . . .
O6 O 0.40415(4) 0.73216(8) 0.10523(14) 0.0336(2) Uani 1 1 d . . . . .
O5 O 0.40601(4) 0.96981(8) 0.10015(14) 0.0340(2) Uani 1 1 d . . . . .
O4 O 0.74796(4) 0.61426(8) 0.67524(15) 0.0401(2) Uani 1 1 d . . . . .
O1 O 0.74939(4) 1.08089(8) 0.69606(16) 0.0430(3) Uani 1 1 d . . . . .
O3 O 0.80855(4) 0.74614(8) 0.80342(16) 0.0430(3) Uani 1 1 d . . . . .
O2 O 0.80983(5) 0.94473(9) 0.80321(17) 0.0463(3) Uani 1 1 d . . . . .
O9 O 0.76176(5) 0.33716(8) 0.74205(19) 0.0485(3) Uani 1 1 d . . . . .
O10 O 0.82803(5) 0.47263(8) 0.81900(18) 0.0494(3) Uani 1 1 d . . . . .
O7 O 0.84422(5) 0.18914(9) 0.8948(2) 0.0541(3) Uani 1 1 d . . . . .
H7 H 0.8097(11) 0.1785(19) 0.821(3) 0.081 Uiso 1 1 d . U . . .
O8 O 0.90865(5) 0.32332(10) 0.9686(2) 0.0645(4) Uani 1 1 d . . . . .
C8 C 0.45239(5) 0.79492(10) 0.17243(18) 0.0269(2) Uani 1 1 d . . . . .
C7 C 0.45270(5) 0.90542(10) 0.17154(18) 0.0277(3) Uani 1 1 d . . . . .
C3 C 0.71489(5) 0.90407(10) 0.61986(17) 0.0257(2) Uani 1 1 d . . . . .
C5 C 0.61309(6) 0.84902(9) 0.43402(17) 0.0252(2) Uani 1 1 d . . . . .
C2 C 0.76138(6) 0.71195(11) 0.70543(19) 0.0300(3) Uani 1 1 d . . . . .
C4 C 0.71483(5) 0.79279(10) 0.61807(17) 0.0251(2) Uani 1 1 d . . . . .
C10 C 0.34975(6) 0.79875(12) 0.0882(2) 0.0363(3) Uani 1 1 d . . . . .
H10A H 0.339914 0.813658 0.211691 0.044 Uiso 1 1 calc R U . . .
H10B H 0.316183 0.758493 0.017176 0.044 Uiso 1 1 calc R U . . .
C6 C 0.55632(6) 0.84909(9) 0.33495(18) 0.0254(2) Uani 1 1 d . . . . .
C1 C 0.76135(6) 0.98269(11) 0.7123(2) 0.0317(3) Uani 1 1 d . . . . .
C12 C 0.81014(6) 0.37091(11) 0.8088(2) 0.0346(3) Uani 1 1 d . . . . .
C9 C 0.35869(6) 0.90534(12) -0.0079(2) 0.0364(3) Uani 1 1 d . . . . .
H9A H 0.369208 0.890241 -0.130426 0.044 Uiso 1 1 calc R U . . .
H9B H 0.321187 0.947225 -0.025198 0.044 Uiso 1 1 calc R U . . .
C11 C 0.85982(6) 0.29313(12) 0.8991(2) 0.0410(3) Uani 1 1 d . . . . .
H10 H 0.7973(11) 0.520(2) 0.764(3) 0.090(8) Uiso 1 1 d . . . . .
H3 H 0.8092(12) 0.854(2) 0.806(4) 0.107(9) Uiso 1 1 d . . . . .
N2 N 0.9987(4) 1.0030(8) 1.0052(13) 0.0375(6) Uani 0.5 1 d D U P A -1
C13 C 0.99573(16) 0.8867(3) 1.0787(6) 0.0561(9) Uani 0.5 1 d D U P A -1
H13A H 1.028578 0.876194 1.182184 0.067 Uiso 0.5 1 calc R U P A -1
H13B H 1.001747 0.834980 0.980647 0.067 Uiso 0.5 1 calc R U P A -1
C14 C 0.9366(5) 0.8601(9) 1.144(2) 0.090(4) Uani 0.5 1 d D U P A -1
H14A H 0.904586 0.858504 1.038621 0.135 Uiso 0.5 1 calc R U P A -1
H14B H 0.927976 0.915825 1.231036 0.135 Uiso 0.5 1 calc R U P A -1
H14C H 0.939520 0.789163 1.204848 0.135 Uiso 0.5 1 calc R U P A -1
C15 C 0.94834(13) 1.0219(3) 0.8448(5) 0.0473(8) Uani 0.5 1 d D U P A -1
H15A H 0.910240 1.020473 0.892939 0.057 Uiso 0.5 1 calc R U P A -1
H15B H 0.952936 1.095630 0.795626 0.057 Uiso 0.5 1 calc R U P A -1
C16 C 0.9443(3) 0.9414(9) 0.6866(12) 0.0644(18) Uani 0.5 1 d D U P A -1
H16A H 0.911969 0.962802 0.589315 0.097 Uiso 0.5 1 calc R U P A -1
H16B H 0.936431 0.868691 0.730646 0.097 Uiso 0.5 1 calc R U P A -1
H16C H 0.981841 0.941022 0.638072 0.097 Uiso 0.5 1 calc R U P A -1
C17 C 1.05924(13) 1.0141(3) 0.9428(5) 0.0485(8) Uani 0.5 1 d D U P A -1
H17A H 1.061949 0.959951 0.845433 0.058 Uiso 0.5 1 calc R U P A -1
H17B H 1.090663 0.997108 1.047592 0.058 Uiso 0.5 1 calc R U P A -1
C18 C 1.0710(5) 1.1272(7) 0.8695(15) 0.062(2) Uani 0.5 1 d D U P A -1
H18A H 1.041708 1.142871 0.760554 0.092 Uiso 0.5 1 calc R U P A -1
H18B H 1.110988 1.129400 0.836939 0.092 Uiso 0.5 1 calc R U P A -1
H18C H 1.067859 1.181626 0.964278 0.092 Uiso 0.5 1 calc R U P A -1
C19 C 0.99089(15) 1.0852(3) 1.1532(5) 0.0485(7) Uani 0.5 1 d D U P A -1
H19A H 0.951260 1.074436 1.188835 0.058 Uiso 0.5 1 calc R U P A -1
H19B H 0.991672 1.158918 1.100513 0.058 Uiso 0.5 1 calc R U P A -1
C1A C 1.0376(3) 1.0792(9) 1.3254(12) 0.0668(18) Uani 0.5 1 d D U P A -1
H1AA H 1.076598 1.097009 1.294131 0.100 Uiso 0.5 1 calc R U P A -1
H1AB H 1.038451 1.005648 1.376205 0.100 Uiso 0.5 1 calc R U P A -1
H1AC H 1.027620 1.131012 1.416443 0.100 Uiso 0.5 1 calc R U P A -1


_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
S2 C5 1.7370(12) . ?
S2 C4 1.7417(13) . ?
S4 C8 1.7403(13) . ?
S4 C6 1.7383(12) . ?
S1 C3 1.7371(12) . ?
S1 C5 1.7391(12) . ?
S3 C7 1.7351(13) . ?
S3 C6 1.7367(12) . ?
O6 C8 1.3582(15) . ?
O6 C10 1.4616(16) . ?
O5 C7 1.3514(14) . ?
O5 C9 1.4546(16) . ?
O4 C2 1.2411(16) . ?
O1 C1 1.2299(16) . ?
O3 C2 1.2565(17) . ?
O3 H3 1.31(3) . ?
O2 C1 1.2742(17) . ?
O2 H3 1.11(3) . ?
O9 C12 1.1967(17) . ?
O10 C12 1.3037(17) . ?
O10 H10 0.94(3) . ?
O7 H7 0.88(2) . ?
O7 C11 1.3159(18) . ?
O8 C11 1.1965(18) . ?
C8 C7 1.3483(18) . ?
C3 C4 1.3579(17) . ?
C3 C1 1.5008(17) . ?
C5 C6 1.3685(19) . ?
C2 C4 1.5075(17) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 C9 1.507(2) . ?
C12 C11 1.5363(19) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
N2 C13 1.523(10) . ?
N2 C15 1.515(10) . ?
N2 C17 1.515(9) . ?
N2 C19 1.505(9) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 C14 1.524(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 C16 1.509(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 C18 1.519(9) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 C1A 1.509(7) . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
C1A H1AC 0.9700 . ?

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
C5 S2 C4 94.99(6) . . ?
C6 S4 C8 93.98(6) . . ?
C3 S1 C5 95.19(6) . . ?
C7 S3 C6 94.38(6) . . ?
C8 O6 C10 109.42(10) . . ?
C7 O5 C9 110.85(10) . . ?
C2 O3 H3 110.2(12) . . ?
C1 O2 H3 111.1(15) . . ?
C12 O10 H10 111.1(15) . . ?
C11 O7 H7 111.3(15) . . ?
O6 C8 S4 117.71(9) . . ?
C7 C8 S4 117.75(9) . . ?
C7 C8 O6 124.51(11) . . ?
O5 C7 S3 117.29(9) . . ?
C8 C7 S3 117.33(9) . . ?
C8 C7 O5 125.38(11) . . ?
C4 C3 S1 116.99(9) . . ?
C4 C3 C1 130.02(11) . . ?
C1 C3 S1 112.97(9) . . ?
S2 C5 S1 115.63(7) . . ?
C6 C5 S2 121.94(9) . . ?
C6 C5 S1 122.42(9) . . ?
O4 C2 O3 125.53(12) . . ?
O4 C2 C4 114.77(12) . . ?
O3 C2 C4 119.68(11) . . ?
C3 C4 S2 117.18(9) . . ?
C3 C4 C2 130.59(11) . . ?
C2 C4 S2 112.22(9) . . ?
O6 C10 H10A 109.6 . . ?
O6 C10 H10B 109.6 . . ?
O6 C10 C9 110.28(11) . . ?
H10A C10 H10B 108.1 . . ?
C9 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
S3 C6 S4 116.52(7) . . ?
C5 C6 S4 121.84(9) . . ?
C5 C6 S3 121.63(9) . . ?
O1 C1 O2 124.19(13) . . ?
O1 C1 C3 116.88(12) . . ?
O2 C1 C3 118.93(11) . . ?
O9 C12 O10 127.27(13) . . ?
O9 C12 C11 121.31(13) . . ?
O10 C12 C11 111.41(12) . . ?
O5 C9 C10 110.81(11) . . ?
O5 C9 H9A 109.5 . . ?
O5 C9 H9B 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
O7 C11 C12 114.26(12) . . ?
O8 C11 O7 122.17(13) . . ?
O8 C11 C12 123.57(13) . . ?
C15 N2 C13 110.2(6) . . ?
C17 N2 C13 106.4(6) . . ?
C17 N2 C15 110.8(6) . . ?
C19 N2 C13 110.6(6) . . ?
C19 N2 C15 107.2(7) . . ?
C19 N2 C17 111.8(6) . . ?
N2 C13 H13A 108.9 . . ?
N2 C13 H13B 108.9 . . ?
N2 C13 C14 113.5(6) . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 H15A 108.3 . . ?
N2 C15 H15B 108.3 . . ?
H15A C15 H15B 107.4 . . ?
C16 C15 N2 116.1(5) . . ?
C16 C15 H15A 108.3 . . ?
C16 C15 H15B 108.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 H17A 108.8 . . ?
N2 C17 H17B 108.8 . . ?
N2 C17 C18 113.8(5) . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 H19A 108.5 . . ?
N2 C19 H19B 108.5 . . ?
N2 C19 C1A 114.9(5) . . ?
H19A C19 H19B 107.5 . . ?
C1A C19 H19A 108.5 . . ?
C1A C19 H19B 108.5 . . ?
C19 C1A H1AA 109.5 . . ?
C19 C1A H1AB 109.5 . . ?
C19 C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?

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
S2 C5 C6 S4 1.35(17) . . . . ?
S2 C5 C6 S3 179.72(7) . . . . ?
S4 C8 C7 S3 0.35(15) . . . . ?
S4 C8 C7 O5 -179.76(10) . . . . ?
S1 C3 C4 S2 -0.47(14) . . . . ?
S1 C3 C4 C2 -179.31(11) . . . . ?
S1 C3 C1 O1 0.41(16) . . . . ?
S1 C3 C1 O2 179.68(11) . . . . ?
S1 C5 C6 S4 -178.06(7) . . . . ?
S1 C5 C6 S3 0.31(17) . . . . ?
O6 C8 C7 S3 178.34(10) . . . . ?
O6 C8 C7 O5 -1.8(2) . . . . ?
O6 C10 C9 O5 -62.58(15) . . . . ?
O4 C2 C4 S2 2.19(15) . . . . ?
O4 C2 C4 C3 -178.93(13) . . . . ?
O3 C2 C4 S2 -176.19(11) . . . . ?
O3 C2 C4 C3 2.7(2) . . . . ?
O9 C12 C11 O7 0.3(2) . . . . ?
O9 C12 C11 O8 -179.46(18) . . . . ?
O10 C12 C11 O7 179.36(15) . . . . ?
O10 C12 C11 O8 -0.4(2) . . . . ?
C8 S4 C6 S3 -2.11(9) . . . . ?
C8 S4 C6 C5 176.34(12) . . . . ?
C8 O6 C10 C9 47.94(15) . . . . ?
C7 S3 C6 S4 2.26(9) . . . . ?
C7 S3 C6 C5 -176.19(12) . . . . ?
C7 O5 C9 C10 41.51(15) . . . . ?
C3 S1 C5 S2 -1.07(8) . . . . ?
C3 S1 C5 C6 178.37(12) . . . . ?
C5 S2 C4 C3 -0.25(11) . . . . ?
C5 S2 C4 C2 178.80(9) . . . . ?
C5 S1 C3 C4 0.92(11) . . . . ?
C5 S1 C3 C1 -177.72(9) . . . . ?
C4 S2 C5 S1 0.88(8) . . . . ?
C4 S2 C5 C6 -178.57(12) . . . . ?
C4 C3 C1 O1 -178.01(13) . . . . ?
C4 C3 C1 O2 1.3(2) . . . . ?
C10 O6 C8 S4 160.14(9) . . . . ?
C10 O6 C8 C7 -17.85(17) . . . . ?
C6 S4 C8 O6 -177.08(10) . . . . ?
C6 S4 C8 C7 1.05(12) . . . . ?
C6 S3 C7 O5 178.56(10) . . . . ?
C6 S3 C7 C8 -1.55(11) . . . . ?
C1 C3 C4 S2 177.90(11) . . . . ?
C1 C3 C4 C2 -0.9(2) . . . . ?
C9 O5 C7 S3 168.95(9) . . . . ?
C9 O5 C7 C8 -10.94(18) . . . . ?
C13 N2 C15 C16 -54.5(9) . . . . ?
C13 N2 C17 C18 -178.4(6) . . . . ?
C13 N2 C19 C1A 60.1(9) . . . . ?
C15 N2 C13 C14 -58.5(10) . . . . ?
C15 N2 C17 C18 61.9(8) . . . . ?
C15 N2 C19 C1A -179.7(7) . . . . ?
C17 N2 C13 C14 -178.7(8) . . . . ?
C17 N2 C15 C16 63.0(9) . . . . ?
C17 N2 C19 C1A -58.1(9) . . . . ?
C19 N2 C13 C14 59.7(10) . . . . ?
C19 N2 C15 C16 -174.8(6) . . . . ?
C19 N2 C17 C18 -57.6(9) . . . . ?

_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
- Detector area scaling
;
####################################################################### 
# 
# 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_191001-eodc-tma-173k-
_database_code_depnum_ccdc_archive 'CCDC 2196211'
loop_
_audit_author_name
_audit_author_address
'Biao Zhou'
;Nihon University
Japan
;
_audit_update_record             
;
2023-02-15 deposited with the CCDC.	2023-02-20 downloaded from the CCDC.
;
_audit_creation_date             2023-02-02
_audit_creation_method           
;
Olex2 1.5-dev
(compiled 2023.01.20 svn.r024a95a1 for OlexSys, GUI svn.r6444)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H5 O6 S4, C4 H12 N'
_chemical_formula_sum            'C14 H17 N O6 S4'
_chemical_formula_weight         423.52
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.8601(2)
_cell_length_b                   13.4801(4)
_cell_length_c                   19.2445(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1779.63(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15035
_cell_measurement_temperature    173
_cell_measurement_theta_max      30.7130
_cell_measurement_theta_min      2.1590
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.946
_exptl_absorpt_coefficient_mu    0.565
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orangish
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18774
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.153
_diffrn_ambient_temperature      173.00
_diffrn_detector_area_resol_mean 7.1429
_diffrn_detector_type            'Rigaku Saturn724+ area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -100.00  80.00   0.50    1.50    --  -10.00  45.00   0.00  360
  2  ω   -100.00  80.00   0.50    1.50    --  -10.00  45.00  90.00  360
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3358
_reflns_number_total             3630
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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 > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.23(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         3630
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0293
_refine_ls_restrained_S_all      1.032
_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/[σ²(Fo²)+(0.0454P)²+0.1896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0739
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.77(9)
 0.23(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 O5-C9 \\sim O5-C9A
 with sigma of 0.02
 O6-C10 \\sim O6-C10A
 with sigma of 0.02
 C9-C10 \\sim C9A-C10A
 with sigma of 0.02
 O5-C10 \\sim O5-C10A
 with sigma of 0.04
 O6-C9 \\sim O6-C9A
 with sigma of 0.04
 O5-C9 \\sim O5-C9A \\sim O6-C10A \\sim O6-C10
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C10A) \\sim Ueq, Uanis(C9A) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.01
5. Rigid body (RIGU) restrains
 O3, H3, O2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(C10A)=Sof(H10C)=Sof(H10D)=1-FVAR(1)
 Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C10)=Sof(H10A)=Sof(H10B)=FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C9A(H9AA,H9AB), C10A(H10C,H10D)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
S1 S 0.41012(11) 0.12687(4) 0.53794(3) 0.02517(16) Uani 1 1 d . . . . .
S2 S 0.40575(11) 0.28040(5) 0.42837(3) 0.02406(16) Uani 1 1 d . . . . .
S4 S 0.41513(10) 0.45117(5) 0.54714(3) 0.02315(16) Uani 1 1 d . . . . .
S3 S 0.41168(11) 0.29456(5) 0.65630(3) 0.02771(17) Uani 1 1 d . . . . .
O5 O 0.4543(3) 0.43501(17) 0.75237(11) 0.0412(6) Uani 1 1 d D . . . .
O6 O 0.4493(3) 0.58811(15) 0.64590(10) 0.0359(5) Uani 1 1 d D . . . .
O4 O 0.4059(3) 0.22451(18) 0.28988(11) 0.0457(6) Uani 1 1 d . . . . .
O1 O 0.4267(4) -0.07155(15) 0.50146(13) 0.0466(6) Uani 1 1 d . . . . .
N1 N 0.5295(3) 0.16199(18) 0.10456(12) 0.0300(6) Uani 1 1 d . . . . .
O3 O 0.4437(3) 0.0615(2) 0.29625(13) 0.0459(6) Uani 1 1 d . . . . .
H3 H 0.449(6) 0.013(3) 0.330(2) 0.071(14) Uiso 1 1 d . . . . .
O2 O 0.4508(3) -0.06312(17) 0.38634(14) 0.0494(6) Uani 1 1 d . . . . .
C12 C 0.6890(5) 0.2091(3) 0.14640(19) 0.0389(7) Uani 1 1 d . . . . .
H12A H 0.694(6) 0.277(3) 0.136(2) 0.058 Uiso 1 1 d . U . . .
H12B H 0.657(5) 0.204(3) 0.197(2) 0.058 Uiso 1 1 d . U . . .
H12C H 0.808(6) 0.176(3) 0.131(2) 0.058 Uiso 1 1 d . U . . .
C11 C 0.3379(4) 0.2077(3) 0.12377(18) 0.0392(7) Uani 1 1 d . . . . .
H11A H 0.313(5) 0.198(3) 0.172(2) 0.059 Uiso 1 1 d . U . . .
H11B H 0.344(5) 0.282(3) 0.116(2) 0.059 Uiso 1 1 d . U . . .
H11C H 0.240(6) 0.171(3) 0.0941(19) 0.059 Uiso 1 1 d . U . . .
C3 C 0.4218(4) 0.08662(19) 0.45185(14) 0.0250(5) Uani 1 1 d . . . . .
C5 C 0.4110(4) 0.25350(18) 0.51752(12) 0.0209(5) Uani 1 1 d . . . . .
C7 C 0.4418(4) 0.4182(2) 0.68235(14) 0.0283(6) Uani 1 1 d . . . . .
C4 C 0.4192(4) 0.15679(19) 0.40195(13) 0.0240(5) Uani 1 1 d . . . . .
C13 C 0.5663(6) 0.1789(2) 0.02895(15) 0.0378(7) Uani 1 1 d . . . . .
H13A H 0.576(6) 0.253(3) 0.0215(18) 0.057 Uiso 1 1 d . U . . .
H13B H 0.695(6) 0.150(3) 0.0178(19) 0.057 Uiso 1 1 d . U . . .
H13C H 0.468(6) 0.151(3) 0.004(2) 0.057 Uiso 1 1 d . U . . .
C6 C 0.4146(4) 0.32372(18) 0.56703(12) 0.0213(5) Uani 1 1 d . . . . .
C8 C 0.4413(4) 0.4879(2) 0.63394(14) 0.0258(6) Uani 1 1 d . . . . .
C14 C 0.5248(6) 0.0531(3) 0.12010(19) 0.0455(9) Uani 1 1 d . . . . .
H14A H 0.655(6) 0.026(3) 0.106(2) 0.068 Uiso 1 1 d . U . . .
H14B H 0.502(5) 0.046(3) 0.169(2) 0.068 Uiso 1 1 d . U . . .
H14C H 0.423(6) 0.029(3) 0.093(2) 0.068 Uiso 1 1 d . U . . .
C1 C 0.4330(4) -0.0246(2) 0.44665(18) 0.0356(7) Uani 1 1 d . . . . .
C2 C 0.4221(4) 0.1484(2) 0.32378(15) 0.0342(7) Uani 1 1 d . . . . .
C9 C 0.5168(10) 0.5358(4) 0.7656(3) 0.042(2) Uani 0.690(16) 1 d D . P A 1
H9A H 0.671414 0.544159 0.753625 0.050 Uiso 0.690(16) 1 calc R U P A 1
H9B H 0.493784 0.554953 0.820034 0.050 Uiso 0.690(16) 1 calc R U P A 1
C10 C 0.3964(11) 0.6019(5) 0.7194(3) 0.041(2) Uani 0.690(16) 1 d D . P A 1
H10A H 0.242227 0.584781 0.726483 0.049 Uiso 0.690(16) 1 calc R U P A 1
H10B H 0.419436 0.679169 0.734016 0.049 Uiso 0.690(16) 1 calc R U P A 1
C9A C 0.407(3) 0.5412(6) 0.7627(7) 0.069(8) Uani 0.310(16) 1 d D U P A 2
H9AA H 0.248988 0.549092 0.758559 0.083 Uiso 0.310(16) 1 calc R U P A 2
H9AB H 0.446770 0.560707 0.815803 0.083 Uiso 0.310(16) 1 calc R U P A 2
C10A C 0.495(4) 0.6142(12) 0.7166(5) 0.061(6) Uani 0.310(16) 1 d D U P A 2
H10C H 0.438817 0.687993 0.728380 0.074 Uiso 0.310(16) 1 calc R U P A 2
H10D H 0.652928 0.615111 0.723890 0.074 Uiso 0.310(16) 1 calc R U P A 2


_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
S1 C3 1.745(3) . ?
S1 C5 1.752(2) . ?
S2 C5 1.754(2) . ?
S2 C4 1.745(3) . ?
S4 C6 1.760(2) . ?
S4 C8 1.751(3) . ?
S3 C7 1.753(3) . ?
S3 C6 1.762(2) . ?
O5 C7 1.369(3) . ?
O5 C9 1.447(5) . ?
O5 C9A 1.481(9) . ?
O6 C8 1.372(3) . ?
O6 C10 1.471(5) . ?
O6 C10A 1.440(8) . ?
O4 C2 1.221(4) . ?
O1 C1 1.231(4) . ?
N1 C12 1.500(4) . ?
N1 C11 1.498(4) . ?
N1 C13 1.494(4) . ?
N1 C14 1.499(4) . ?
O3 H3 0.92(5) . ?
O3 C2 1.294(4) . ?
O2 C1 1.277(4) . ?
C12 H12A 0.93(4) . ?
C12 H12B 1.01(4) . ?
C12 H12C 0.98(4) . ?
C11 H11A 0.95(4) . ?
C11 H11B 1.01(4) . ?
C11 H11C 1.01(4) . ?
C3 C4 1.348(4) . ?
C3 C1 1.505(4) . ?
C5 C6 1.343(3) . ?
C7 C8 1.323(4) . ?
C4 C2 1.509(4) . ?
C13 H13A 1.02(4) . ?
C13 H13B 0.99(4) . ?
C13 H13C 0.91(4) . ?
C14 H14A 1.00(4) . ?
C14 H14B 0.96(5) . ?
C14 H14C 0.92(4) . ?
C9 H9A 1.0910 . ?
C9 H9B 1.0910 . ?
C9 C10 1.505(8) . ?
C10 H10A 1.0910 . ?
C10 H10B 1.0910 . ?
C9A H9AA 1.0910 . ?
C9A H9AB 1.0910 . ?
C9A C10A 1.457(18) . ?
C10A H10C 1.0910 . ?
C10A H10D 1.0910 . ?

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
C3 S1 C5 95.16(11) . . ?
C4 S2 C5 94.97(12) . . ?
C8 S4 C6 93.93(12) . . ?
C7 S3 C6 93.75(12) . . ?
C7 O5 C9 110.3(3) . . ?
C7 O5 C9A 106.1(6) . . ?
C8 O6 C10 106.0(3) . . ?
C8 O6 C10A 114.1(7) . . ?
C11 N1 C12 109.5(2) . . ?
C11 N1 C14 109.6(3) . . ?
C13 N1 C12 109.6(3) . . ?
C13 N1 C11 109.0(2) . . ?
C13 N1 C14 110.3(2) . . ?
C14 N1 C12 108.9(3) . . ?
C2 O3 H3 110(3) . . ?
N1 C12 H12A 109(2) . . ?
N1 C12 H12B 109(2) . . ?
N1 C12 H12C 105(2) . . ?
H12A C12 H12B 106(3) . . ?
H12A C12 H12C 111(3) . . ?
H12B C12 H12C 116(3) . . ?
N1 C11 H11A 110(2) . . ?
N1 C11 H11B 110(2) . . ?
N1 C11 H11C 104(2) . . ?
H11A C11 H11B 107(3) . . ?
H11A C11 H11C 111(3) . . ?
H11B C11 H11C 115(3) . . ?
C4 C3 S1 117.22(19) . . ?
C4 C3 C1 130.7(3) . . ?
C1 C3 S1 112.0(2) . . ?
S1 C5 S2 114.88(13) . . ?
C6 C5 S1 121.85(19) . . ?
C6 C5 S2 123.26(19) . . ?
O5 C7 S3 116.5(2) . . ?
C8 C7 S3 118.3(2) . . ?
C8 C7 O5 125.1(3) . . ?
C3 C4 S2 117.60(19) . . ?
C3 C4 C2 131.1(3) . . ?
C2 C4 S2 111.3(2) . . ?
N1 C13 H13A 107(2) . . ?
N1 C13 H13B 108(2) . . ?
N1 C13 H13C 109(3) . . ?
H13A C13 H13B 108(3) . . ?
H13A C13 H13C 112(3) . . ?
H13B C13 H13C 112(3) . . ?
S4 C6 S3 115.45(14) . . ?
C5 C6 S4 122.26(19) . . ?
C5 C6 S3 122.27(19) . . ?
O6 C8 S4 116.2(2) . . ?
C7 C8 S4 118.1(2) . . ?
C7 C8 O6 125.5(3) . . ?
N1 C14 H14A 106(2) . . ?
N1 C14 H14B 108(3) . . ?
N1 C14 H14C 104(3) . . ?
H14A C14 H14B 112(3) . . ?
H14A C14 H14C 113(3) . . ?
H14B C14 H14C 113(3) . . ?
O1 C1 O2 125.0(3) . . ?
O1 C1 C3 117.0(3) . . ?
O2 C1 C3 118.0(3) . . ?
O4 C2 O3 123.5(3) . . ?
O4 C2 C4 117.9(3) . . ?
O3 C2 C4 118.6(3) . . ?
O5 C9 H9A 110.4 . . ?
O5 C9 H9B 110.4 . . ?
O5 C9 C10 106.8(5) . . ?
H9A C9 H9B 108.6 . . ?
C10 C9 H9A 110.4 . . ?
C10 C9 H9B 110.4 . . ?
O6 C10 C9 111.0(5) . . ?
O6 C10 H10A 109.4 . . ?
O6 C10 H10B 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O5 C9A H9AA 107.6 . . ?
O5 C9A H9AB 107.6 . . ?
H9AA C9A H9AB 107.1 . . ?
C10A C9A O5 118.7(14) . . ?
C10A C9A H9AA 107.6 . . ?
C10A C9A H9AB 107.6 . . ?
O6 C10A C9A 108.6(12) . . ?
O6 C10A H10C 110.0 . . ?
O6 C10A H10D 110.0 . . ?
C9A C10A H10C 110.0 . . ?
C9A C10A H10D 110.0 . . ?
H10C C10A H10D 108.4 . . ?

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
S1 C3 C4 S2 0.3(3) . . . . ?
S1 C3 C4 C2 -178.3(3) . . . . ?
S1 C3 C1 O1 2.1(3) . . . . ?
S1 C3 C1 O2 -177.0(2) . . . . ?
S1 C5 C6 S4 -179.91(17) . . . . ?
S1 C5 C6 S3 -1.9(4) . . . . ?
S2 C5 C6 S4 -0.2(4) . . . . ?
S2 C5 C6 S3 177.86(17) . . . . ?
S2 C4 C2 O4 -3.4(4) . . . . ?
S2 C4 C2 O3 175.9(2) . . . . ?
S3 C7 C8 S4 -1.2(3) . . . . ?
S3 C7 C8 O6 175.1(2) . . . . ?
O5 C7 C8 S4 -177.7(2) . . . . ?
O5 C7 C8 O6 -1.3(5) . . . . ?
O5 C9 C10 O6 -69.2(8) . . . . ?
O5 C9A C10A O6 56(3) . . . . ?
C3 S1 C5 S2 4.04(18) . . . . ?
C3 S1 C5 C6 -176.2(2) . . . . ?
C3 C4 C2 O4 175.3(3) . . . . ?
C3 C4 C2 O3 -5.4(5) . . . . ?
C5 S1 C3 C4 -2.7(2) . . . . ?
C5 S1 C3 C1 177.5(2) . . . . ?
C5 S2 C4 C3 2.2(3) . . . . ?
C5 S2 C4 C2 -178.9(2) . . . . ?
C7 S3 C6 S4 -7.01(18) . . . . ?
C7 S3 C6 C5 174.8(2) . . . . ?
C7 O5 C9 C10 46.5(6) . . . . ?
C7 O5 C9A C10A -45(2) . . . . ?
C4 S2 C5 S1 -3.9(2) . . . . ?
C4 S2 C5 C6 176.3(2) . . . . ?
C4 C3 C1 O1 -177.8(3) . . . . ?
C4 C3 C1 O2 3.2(5) . . . . ?
C6 S4 C8 O6 -179.9(2) . . . . ?
C6 S4 C8 C7 -3.2(3) . . . . ?
C6 S3 C7 O5 -178.3(2) . . . . ?
C6 S3 C7 C8 5.0(2) . . . . ?
C8 S4 C6 S3 6.54(18) . . . . ?
C8 S4 C6 C5 -175.3(2) . . . . ?
C8 O6 C10 C9 51.4(6) . . . . ?
C8 O6 C10A C9A -35(2) . . . . ?
C1 C3 C4 S2 -179.8(2) . . . . ?
C1 C3 C4 C2 1.5(5) . . . . ?
C9 O5 C7 S3 168.7(3) . . . . ?
C9 O5 C7 C8 -14.7(5) . . . . ?
C10 O6 C8 S4 159.0(3) . . . . ?
C10 O6 C8 C7 -17.4(4) . . . . ?
C9A O5 C7 S3 -159.9(9) . . . . ?
C9A O5 C7 C8 16.7(9) . . . . ?
C10A O6 C8 S4 -172.6(12) . . . . ?
C10A O6 C8 C7 11.0(12) . . . . ?

_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
- Detector area scaling
;
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.77(9)
2 0.23(9)

