# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_c1bf4
_database_code_depnum_ccdc_archive 'CCDC 2152717'
loop_
_audit_author_name
_audit_author_address
'Shuqin Qin'
;Jinan University
China
;
_audit_update_record             
;
2022-02-17 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_audit_creation_date             2021-12-14
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 O6 S2, C10 H11 O2, 2(C H6 N3)'
_chemical_formula_sum            'C24 H31 N6 O8 S2'
_chemical_formula_weight         595.67
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2266(9)
_cell_length_b                   7.1344(7)
_cell_length_c                   14.1593(15)
_cell_angle_alpha                97.548(9)
_cell_angle_beta                 90.802(11)
_cell_angle_gamma                94.115(10)
_cell_volume                     621.77(13)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2138
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      28.6590
_cell_measurement_theta_min      2.8810
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.939
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.591
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             313
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2175
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         3.557
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  37.00   1.00    4.00    --   11.74 -57.00 -30.00   96
  2  ω    -16.00  79.00   1.00    4.00    --   11.74  77.00-120.00   95
  3  ω    -16.00  82.00   1.00    4.00    --   11.74  57.00 120.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1100039000
_diffrn_orient_matrix_UB_12      0.0103497000
_diffrn_orient_matrix_UB_13      0.0103010000
_diffrn_orient_matrix_UB_21      0.0188915000
_diffrn_orient_matrix_UB_22      -0.0207525000
_diffrn_orient_matrix_UB_23      0.0469113000
_diffrn_orient_matrix_UB_31      0.0243583000
_diffrn_orient_matrix_UB_32      0.0978552000
_diffrn_orient_matrix_UB_33      0.0157528000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1803
_reflns_number_total             2175
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.797
_refine_diff_density_min         -0.728
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         2175
_refine_ls_number_restraints     337
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0789
_refine_ls_restrained_S_all      1.054
_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)+(0.1184P)²+1.0201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2101
_refine_ls_wR_factor_ref         0.2220
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.673(12)
 0.327(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C5-O5 = O5-C10
 1.42 with sigma of 0.02
 C4-O4
 1.32 with sigma of 0.02
 C8-C9
 1.52 with sigma of 0.02
 C2-C1
 1.39 with sigma of 0.02
 C1-C7
 1.52 with sigma of 0.02
 C7-C8
 1.32 with sigma of 0.02
 C2-C7
 2.521 with sigma of 0.04
 C9-C7
 2.462 with sigma of 0.04
 C1-C8
 2.462 with sigma of 0.04
 C14A-C13 \\sim C15A-C14A \\sim C16-C15A \\sim C11A-C16 \\sim C12A-C11A \\sim
C12A-C13
 with sigma of 0.02
 C14-C13 \\sim C15-C14 \\sim C16-C15 \\sim C11-C16 \\sim C12-C11 \\sim C12-C13
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
O4 \\sim O5 \\sim C1 \\sim C6 \\sim C5 \\sim C4 \\sim C3 \\sim C2 \\sim C7
\\sim C8 \\sim C9 \\sim C10: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
Uanis(C1) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C7) \\sim
Ueq, Uanis(C6) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C3)
\\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(O4) \\sim Ueq,
Uanis(C10) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
5. Rigid body (RIGU) restrains
 O4, O5, C1, C6, C5, C4, C3, C2, C7, C8, C9, C10
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C11, C12, C13, C14, C15, C16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C11A, C12A, C13, C14A, C15A, C16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=
 Sof(H15A)=1-FVAR(1)
 Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=FVAR(1)
 Fixed Sof: O4(0.5) O5(0.5) C1(0.5) C6(0.5) H6(0.5) C5(0.5) C4(0.5) C3(0.5)
 H3(0.5) C2(0.5) H2(0.5) C7(0.5) H7(0.5) C8(0.5) H8(0.5) C9(0.5) H9A(0.5)
 H9B(0.5) H9C(0.5) C10(0.5) H10A(0.5) H10B(0.5) H10C(0.5)
7.a Riding coordinates:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
7.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C2(H2), C7(H7), C8(H8), C11(H11), C11A(H11A), C12(H12),
 C12A(H12A), C14(H14), C14A(H14A), C15(H15), C15A(H15A)
7.c Fitted hexagon refined as free rotating group:
 C1(C6,C5,C4,C3,C2)
7.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), N3(H3A,H3B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.83774(15) 0.24356(13) 0.85957(7) 0.0171(4) Uani 1 1 d . . . . .
O1 O 0.9472(5) 0.1252(4) 0.9181(2) 0.0240(7) Uani 1 1 d . . . . .
O2 O 0.6045(4) 0.2252(4) 0.8683(2) 0.0212(7) Uani 1 1 d . . . . .
O3 O 0.9220(5) 0.4400(4) 0.8746(2) 0.0232(7) Uani 1 1 d . . . . .
O4 O -0.295(4) 0.585(2) 0.6391(16) 0.168(5) Uani 0.5 1 d D U P A -1
O5 O -0.235(5) 0.441(4) 0.4240(17) 0.193(6) Uani 0.5 1 d D U P A -1
C1 C 0.317(3) 0.529(4) 0.531(2) 0.177(5) Uani 0.5 1 d DG U P A -1
C6 C 0.147(5) 0.496(4) 0.4655(15) 0.182(6) Uani 0.5 1 d G U P A -1
H6 H 0.172958 0.458769 0.401516 0.218 Uiso 0.5 1 calc R U P A -1
C5 C -0.063(4) 0.517(5) 0.495(2) 0.189(5) Uani 0.5 1 d DG U P A -1
C4 C -0.103(3) 0.573(4) 0.591(2) 0.179(6) Uani 0.5 1 d DG U P A -1
C3 C 0.068(5) 0.606(3) 0.6568(15) 0.176(5) Uani 0.5 1 d G U P A -1
H3 H 0.041397 0.643288 0.720741 0.211 Uiso 0.5 1 calc R U P A -1
C2 C 0.277(4) 0.585(3) 0.627(2) 0.169(5) Uani 0.5 1 d DG U P A -1
H2 H 0.391424 0.607279 0.671280 0.203 Uiso 0.5 1 calc R U P A -1
C7 C 0.533(4) 0.490(8) 0.490(3) 0.179(6) Uani 0.5 1 d D U P A -1
H7 H 0.547382 0.425563 0.429249 0.215 Uiso 0.5 1 calc R U P A -1
C8 C 0.695(5) 0.553(5) 0.545(3) 0.183(7) Uani 0.5 1 d D U P A -1
H8 H 0.658449 0.670910 0.573203 0.219 Uiso 0.5 1 calc R U P A -1
C9 C 0.906(6) 0.533(5) 0.585(2) 0.175(9) Uani 0.5 1 d D U P A -1
H9A H 0.934740 0.401843 0.570533 0.262 Uiso 0.5 1 d R U P A -1
H9B H 0.843210 0.554433 0.646243 0.262 Uiso 0.5 1 d R U P A -1
H9C H 1.037790 0.610933 0.584083 0.262 Uiso 0.5 1 d R U P A -1
C10 C -0.442(5) 0.418(4) 0.383(2) 0.172(8) Uani 0.5 1 d D U P A -1
H10A H -0.432497 0.399709 0.314569 0.259 Uiso 0.5 1 d R U P A -1
H10B H -0.516577 0.529379 0.402269 0.259 Uiso 0.5 1 d R U P A -1
H10C H -0.518257 0.309819 0.403329 0.259 Uiso 0.5 1 d R U P A -1
C11 C 1.1251(16) 0.032(2) 0.6256(6) 0.025(3) Uani 0.50(2) 1 d D . P B 1
H11 H 1.260438 -0.009413 0.610978 0.029 Uiso 0.50(2) 1 calc R U P B 1
C11A C 1.1461(14) 0.131(2) 0.6075(7) 0.025(3) Uani 0.50(2) 1 d D . P B 2
H11A H 1.281860 0.155232 0.583394 0.030 Uiso 0.50(2) 1 calc R U P B 2
C12 C 1.0831(16) 0.089(2) 0.7202(7) 0.028(3) Uani 0.50(2) 1 d D . P B 1
H12 H 1.183463 0.079897 0.768297 0.033 Uiso 0.50(2) 1 calc R U P B 1
C12A C 1.0991(14) 0.189(2) 0.7019(7) 0.027(3) Uani 0.50(2) 1 d D . P B 2
H12A H 1.208620 0.251152 0.742192 0.033 Uiso 0.50(2) 1 calc R U P B 2
C13 C 0.8905(6) 0.1587(6) 0.7398(3) 0.0193(8) Uani 1 1 d D . . . .
C14 C 0.7271(15) 0.156(2) 0.6755(6) 0.025(2) Uani 0.50(2) 1 d D . P B 1
H14 H 0.592000 0.194234 0.693216 0.029 Uiso 0.50(2) 1 calc R U P B 1
C14A C 0.7365(15) 0.063(2) 0.6762(6) 0.022(2) Uani 0.50(2) 1 d D . P B 2
H14A H 0.597607 0.040292 0.697573 0.026 Uiso 0.50(2) 1 calc R U P B 2
C15 C 0.7734(15) 0.094(2) 0.5820(7) 0.029(3) Uani 0.50(2) 1 d D . P B 1
H15 H 0.664423 0.091816 0.536154 0.034 Uiso 0.50(2) 1 calc R U P B 1
C15A C 0.7796(15) -0.002(2) 0.5826(7) 0.027(3) Uani 0.50(2) 1 d D . P B 2
H15A H 0.672572 -0.067844 0.542433 0.032 Uiso 0.50(2) 1 calc R U P B 2
C16 C 0.9774(6) 0.0329(6) 0.5508(3) 0.0227(9) Uani 1 1 d D . . . .
C17 C 0.4580(7) 0.7370(6) 0.9020(3) 0.0219(9) Uani 1 1 d . . . . .
N1 N 0.6710(6) 0.7601(5) 0.8987(3) 0.0309(10) Uani 1 1 d . . . . .
H1A H 0.746863 0.663710 0.897496 0.037 Uiso 1 1 calc R U . . .
H1B H 0.733243 0.871374 0.897759 0.037 Uiso 1 1 calc R U . . .
N2 N 0.3650(6) 0.5654(5) 0.9034(3) 0.0240(9) Uani 1 1 d . . . . .
H2A H 0.227100 0.548922 0.905660 0.029 Uiso 1 1 calc R U . . .
H2B H 0.442315 0.469920 0.902023 0.029 Uiso 1 1 calc R U . . .
N3 N 0.3425(6) 0.8859(5) 0.9040(3) 0.0284(9) Uani 1 1 d . . . . .
H3A H 0.204411 0.871759 0.906309 0.034 Uiso 1 1 calc R U . . .
H3B H 0.405457 0.996953 0.903080 0.034 Uiso 1 1 calc R U . . .


_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 O1 1.454(3) . ?
S1 O2 1.457(3) . ?
S1 O3 1.448(3) . ?
S1 C13 1.767(4) . ?
O4 C4 1.391(18) . ?
O5 C5 1.483(18) . ?
O5 C10 1.40(2) . ?
C1 C6 1.3900 . ?
C1 C2 1.3900 . ?
C1 C7 1.504(18) . ?
C6 H6 0.9300 . ?
C6 C5 1.3900 . ?
C5 C4 1.3900 . ?
C4 C3 1.3900 . ?
C3 H3 0.9300 . ?
C3 C2 1.3900 . ?
C2 H2 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.281(19) . ?
C8 H8 0.9300 . ?
C8 C9 1.446(18) . ?
C9 H9A 0.9601 . ?
C9 H9B 0.9602 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9598 . ?
C10 H10B 0.9601 . ?
C10 H10C 0.9601 . ?
C11 H11 0.9300 . ?
C11 C12 1.381(10) . ?
C11 C16 1.395(9) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.388(10) . ?
C11A C16 1.400(9) . ?
C12 H12 0.9300 . ?
C12 C13 1.350(8) . ?
C12A H12A 0.9300 . ?
C12A C13 1.426(8) . ?
C13 C14 1.353(9) . ?
C13 C14A 1.385(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(10) . ?
C14A H14A 0.9300 . ?
C14A C15A 1.381(10) . ?
C15 H15 0.9300 . ?
C15 C16 1.429(9) . ?
C15A H15A 0.9300 . ?
C15A C16 1.335(9) . ?
C16 C16 1.490(8) 2_756 ?
C17 N1 1.327(5) . ?
C17 N2 1.319(5) . ?
C17 N3 1.323(6) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?

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 S1 O2 112.63(17) . . ?
O1 S1 C13 106.50(18) . . ?
O2 S1 C13 106.24(18) . . ?
O3 S1 O1 113.00(18) . . ?
O3 S1 O2 111.79(17) . . ?
O3 S1 C13 106.06(18) . . ?
C10 O5 C5 157(3) . . ?
C6 C1 C2 120.0 . . ?
C6 C1 C7 114(2) . . ?
C2 C1 C7 126(2) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C5 O5 116(3) . . ?
C4 C5 O5 123(3) . . ?
C4 C5 C6 120.0 . . ?
C5 C4 O4 131(3) . . ?
C5 C4 C3 120.0 . . ?
C3 C4 O4 109(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C7 H7 122.6 . . ?
C8 C7 C1 115(3) . . ?
C8 C7 H7 122.6 . . ?
C7 C8 H8 104.3 . . ?
C7 C8 C9 151(4) . . ?
C9 C8 H8 104.3 . . ?
C8 C9 H9A 107.4 . . ?
C8 C9 H9B 87.2 . . ?
C8 C9 H9C 130.7 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O5 C10 H10A 109.7 . . ?
O5 C10 H10B 109.4 . . ?
O5 C10 H10C 109.2 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 H11 118.0 . . ?
C12 C11 C16 124.1(8) . . ?
C16 C11 H11 118.0 . . ?
C12A C11A H11A 121.9 . . ?
C12A C11A C16 116.2(7) . . ?
C16 C11A H11A 121.9 . . ?
C11 C12 H12 121.4 . . ?
C13 C12 C11 117.3(8) . . ?
C13 C12 H12 121.4 . . ?
C11A C12A H12A 118.5 . . ?
C11A C12A C13 122.9(8) . . ?
C13 C12A H12A 118.5 . . ?
C12 C13 S1 118.2(5) . . ?
C12 C13 C14 124.8(7) . . ?
C12A C13 S1 120.9(4) . . ?
C14 C13 S1 116.9(5) . . ?
C14A C13 S1 123.7(5) . . ?
C14A C13 C12A 115.3(6) . . ?
C13 C14 H14 122.0 . . ?
C13 C14 C15 115.9(8) . . ?
C15 C14 H14 122.0 . . ?
C13 C14A H14A 118.5 . . ?
C15A C14A C13 123.1(8) . . ?
C15A C14A H14A 118.5 . . ?
C14 C15 H15 117.8 . . ?
C14 C15 C16 124.5(8) . . ?
C16 C15 H15 117.8 . . ?
C14A C15A H15A 120.5 . . ?
C16 C15A C14A 118.9(8) . . ?
C16 C15A H15A 120.5 . . ?
C11 C16 C15 113.0(6) . . ?
C11 C16 C16 123.7(6) . 2_756 ?
C11A C16 C16 117.6(5) . 2_756 ?
C15 C16 C16 123.2(6) . 2_756 ?
C15A C16 C11A 123.5(7) . . ?
C15A C16 C16 118.9(6) . 2_756 ?
N2 C17 N1 119.3(4) . . ?
N2 C17 N3 121.1(4) . . ?
N3 C17 N1 119.7(4) . . ?
C17 N1 H1A 120.0 . . ?
C17 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C17 N2 H2A 120.0 . . ?
C17 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C17 N3 H3A 120.0 . . ?
C17 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?

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 C13 C14 C15 178.4(7) . . . . ?
S1 C13 C14A C15A 179.5(7) . . . . ?
O1 S1 C13 C12 -33.8(9) . . . . ?
O1 S1 C13 C12A -71.8(8) . . . . ?
O1 S1 C13 C14 141.7(8) . . . . ?
O1 S1 C13 C14A 109.4(8) . . . . ?
O2 S1 C13 C12 -154.1(9) . . . . ?
O2 S1 C13 C12A 167.9(8) . . . . ?
O2 S1 C13 C14 21.4(8) . . . . ?
O2 S1 C13 C14A -10.9(8) . . . . ?
O3 S1 C13 C12 86.8(9) . . . . ?
O3 S1 C13 C12A 48.9(8) . . . . ?
O3 S1 C13 C14 -97.7(8) . . . . ?
O3 S1 C13 C14A -130.0(8) . . . . ?
O4 C4 C3 C2 174(2) . . . . ?
O5 C5 C4 O4 -6(3) . . . . ?
O5 C5 C4 C3 167(3) . . . . ?
C1 C6 C5 O5 -168(3) . . . . ?
C1 C6 C5 C4 0.0 . . . . ?
C1 C7 C8 C9 140(7) . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C6 C1 C7 C8 168(4) . . . . ?
C6 C5 C4 O4 -173(3) . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C2 C1 C7 C8 -16(6) . . . . ?
C7 C1 C6 C5 177(3) . . . . ?
C7 C1 C2 C3 -176(3) . . . . ?
C10 O5 C5 C6 -162(6) . . . . ?
C10 O5 C5 C4 30(9) . . . . ?
C11 C12 C13 S1 -176.9(7) . . . . ?
C11 C12 C13 C14 8.0(14) . . . . ?
C11A C12A C13 S1 -177.8(8) . . . . ?
C11A C12A C13 C14A 1.2(13) . . . . ?
C12 C11 C16 C15 -1.7(13) . . . . ?
C12 C11 C16 C16 -178.6(8) . . . 2_756 ?
C12 C13 C14 C15 -6.5(13) . . . . ?
C12A C11A C16 C15A 1.3(13) . . . . ?
C12A C11A C16 C16 -179.7(8) . . . 2_756 ?
C12A C13 C14A C15A 0.6(13) . . . . ?
C13 C14 C15 C16 0.5(15) . . . . ?
C13 C14A C15A C16 -1.3(15) . . . . ?
C14 C15 C16 C11 3.3(14) . . . . ?
C14 C15 C16 C16 -179.8(8) . . . 2_756 ?
C14A C15A C16 C11A 0.3(13) . . . . ?
C14A C15A C16 C16 -178.7(8) . . . 2_756 ?
C16 C11 C12 C13 -3.5(15) . . . . ?
C16 C11A C12A C13 -2.0(15) . . . . ?

_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 1.712
_oxdiff_exptl_absorpt_empirical_full_min 0.614
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.673(12)
2 0.327(12)

####################################################################### 
# 
# 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-k_2
_database_code_depnum_ccdc_archive 'CCDC 2152718'
loop_
_audit_author_name
_audit_author_address
'Shuqin Qin'
;Jinan University
China
;
_audit_update_record             
;
2022-02-17 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_audit_creation_date             2021-12-13
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 O6 S2, C8 H8 O2, 2(C H6 N3)'
_chemical_formula_sum            'C22 H28 N6 O8 S2'
_chemical_formula_weight         568.62
_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 0.0181 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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4141(3)
_cell_length_b                   12.8303(7)
_cell_length_c                   15.1362(9)
_cell_angle_alpha                69.146(5)
_cell_angle_beta                 86.884(4)
_cell_angle_gamma                77.000(4)
_cell_volume                     1310.50(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5910
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.7840
_cell_measurement_theta_min      3.7600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.351
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.441
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8801
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.940
_diffrn_reflns_theta_min         3.126
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      9.00  49.00   1.00    1.00    --   40.73 -99.00 120.00   40
  2  ω     29.00 108.00   1.00    1.50    --  107.58 -94.00   0.00   79
  3  ω     65.00 138.00   1.00    1.50    --  107.58 -77.00  90.00   73
  4  ω     57.00 170.00   1.00    1.50    --  107.58  15.00  90.00  113
  5  ω    119.00 174.00   1.00    1.50    --  107.58 125.00  60.00   55
  6  ω     94.00 126.00   1.00    1.50    --  107.58 131.00  82.00   32
  7  ω     83.00 166.00   1.00    1.50    --  107.58  45.00 150.00   83
  8  ω     37.00  65.00   1.00    1.50    --  107.58 -94.00 150.00   28
  9  ω     32.00 114.00   1.00    1.50    --  107.58 -30.00 120.00   82
 10  ω     36.00 127.00   1.00    1.50    --  107.58 -61.00   0.00   91
 11  ω     47.00  96.00   1.00    1.00    --   40.73-125.00-150.00   49
 12  ω     36.00 118.00   1.00    1.50    --  107.58-125.00 -60.00   82
 13  ω    -25.00  51.00   1.00    1.00    --   40.73 -37.00 150.00   76
 14  ω    -28.00  -2.00   1.00    1.00    --  -40.73 125.00  30.00   26
 15  ω   -105.00 -30.00   1.00    1.00    --  -40.73 -37.00-120.00   75
 16  ω   -117.00 -15.00   1.00    1.00    --  -40.73 -77.00   0.00  102
 17  ω    108.00 133.00   1.00    1.50    --  107.58 125.00-120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0591068000
_diffrn_orient_matrix_UB_12      -0.1209776000
_diffrn_orient_matrix_UB_13      0.0744431000
_diffrn_orient_matrix_UB_21      -0.0550014000
_diffrn_orient_matrix_UB_22      0.0487534000
_diffrn_orient_matrix_UB_23      0.0794988000
_diffrn_orient_matrix_UB_31      -0.1974716000
_diffrn_orient_matrix_UB_32      -0.0184315000
_diffrn_orient_matrix_UB_33      -0.0031875000
_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'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4704
_reflns_number_total             5127
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.046
_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)+(0.0519P)²+0.4026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0953
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13),
 C14(H14), C16(H16), C17(H17), C19(H19), C20(H20)
2.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), N3(H3A,H3B), N4(H4A,H4B), N5(H5A,H5B), N6(H6A,H6B)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.66929(5) 0.64024(3) 0.87359(2) 0.01824(10) Uani 1 1 d . . . . .
S2 S 1.05996(5) 0.83749(3) 0.15773(2) 0.01846(10) Uani 1 1 d . . . . .
O1 O 0.50841(14) 0.59098(9) 0.87775(8) 0.0252(2) Uani 1 1 d . . . . .
O2 O 0.61954(14) 0.74993(8) 0.88804(7) 0.0214(2) Uani 1 1 d . . . . .
O3 O 0.82289(15) 0.56091(9) 0.93517(7) 0.0249(2) Uani 1 1 d . . . . .
O4 O 0.88817(14) 0.91169(9) 0.10859(7) 0.0232(2) Uani 1 1 d . . . . .
O5 O 1.21179(14) 0.89732(9) 0.14012(7) 0.0235(2) Uani 1 1 d . . . . .
O6 O 1.10700(14) 0.73036(9) 0.13955(7) 0.0222(2) Uani 1 1 d . . . . .
O7 O 0.53182(18) 0.05133(10) 0.61845(9) 0.0349(3) Uani 1 1 d . . . . .
O8 O 0.6746(2) 0.53449(12) 0.34276(11) 0.0485(4) Uani 1 1 d . . . . .
C1 C 0.5694(2) 0.14923(14) 0.55393(12) 0.0268(3) Uani 1 1 d . . . . .
C2 C 0.5603(2) 0.24939(14) 0.57274(12) 0.0279(3) Uani 1 1 d . . . . .
H2 H 0.526719 0.252732 0.631934 0.033 Uiso 1 1 calc R U . . .
C3 C 0.6020(2) 0.34320(14) 0.50194(12) 0.0293(3) Uani 1 1 d . . . . .
H3 H 0.597761 0.409795 0.514157 0.035 Uiso 1 1 calc R U . . .
C4 C 0.6504(2) 0.34003(14) 0.41272(12) 0.0288(3) Uani 1 1 d . . . . .
C5 C 0.6600(2) 0.23932(14) 0.39492(12) 0.0292(3) Uani 1 1 d . . . . .
H5 H 0.693997 0.236122 0.335729 0.035 Uiso 1 1 calc R U . . .
C6 C 0.6191(2) 0.14423(14) 0.46513(12) 0.0297(3) Uani 1 1 d . . . . .
H6 H 0.624784 0.077372 0.453100 0.036 Uiso 1 1 calc R U . . .
C7 C 0.6883(3) 0.44131(16) 0.33640(13) 0.0368(4) Uani 1 1 d . . . . .
H7 H 0.725554 0.433429 0.279011 0.044 Uiso 1 1 calc R U . . .
C8 C 0.4789(2) 0.05133(16) 0.71039(13) 0.0356(4) Uani 1 1 d . . . . .
H8A H 0.371352 0.111293 0.705102 0.053 Uiso 1 1 calc R U . . .
H8B H 0.578685 0.063718 0.740535 0.053 Uiso 1 1 calc R U . . .
H8C H 0.451165 -0.021023 0.747454 0.053 Uiso 1 1 calc R U . . .
C9 C 0.74899(19) 0.67109(12) 0.75664(10) 0.0188(3) Uani 1 1 d . . . . .
C10 C 0.7697(2) 0.78026(13) 0.70352(11) 0.0249(3) Uani 1 1 d . . . . .
H10 H 0.746580 0.836925 0.730116 0.030 Uiso 1 1 calc R U . . .
C11 C 0.8250(2) 0.80523(13) 0.61069(11) 0.0258(3) Uani 1 1 d . . . . .
H11 H 0.837741 0.878977 0.575343 0.031 Uiso 1 1 calc R U . . .
C12 C 0.86168(19) 0.72159(12) 0.56948(10) 0.0203(3) Uani 1 1 d . . . . .
C13 C 0.8438(2) 0.61141(13) 0.62545(11) 0.0261(3) Uani 1 1 d . . . . .
H13 H 0.870090 0.553878 0.599781 0.031 Uiso 1 1 calc R U . . .
C14 C 0.7881(2) 0.58575(13) 0.71804(11) 0.0258(3) Uani 1 1 d . . . . .
H14 H 0.777011 0.511863 0.754063 0.031 Uiso 1 1 calc R U . . .
C15 C 0.91461(19) 0.74957(12) 0.46880(10) 0.0201(3) Uani 1 1 d . . . . .
C16 C 0.9727(2) 0.85074(13) 0.41856(10) 0.0225(3) Uani 1 1 d . . . . .
H16 H 0.978867 0.901516 0.448850 0.027 Uiso 1 1 calc R U . . .
C17 C 1.0213(2) 0.87674(12) 0.32484(10) 0.0216(3) Uani 1 1 d . . . . .
H17 H 1.058641 0.944589 0.292445 0.026 Uiso 1 1 calc R U . . .
C18 C 1.01372(19) 0.80074(12) 0.27947(10) 0.0191(3) Uani 1 1 d . . . . .
C19 C 0.9549(2) 0.70045(12) 0.32720(10) 0.0231(3) Uani 1 1 d . . . . .
H19 H 0.948626 0.650135 0.296462 0.028 Uiso 1 1 calc R U . . .
C20 C 0.9054(2) 0.67555(13) 0.42088(11) 0.0241(3) Uani 1 1 d . . . . .
H20 H 0.865399 0.608419 0.452463 0.029 Uiso 1 1 calc R U . . .
C21 C 0.9086(2) 1.20256(12) 0.08876(10) 0.0212(3) Uani 1 1 d . . . . .
C22 C 0.3697(2) 0.31440(13) 0.88878(10) 0.0219(3) Uani 1 1 d . . . . .
N1 N 0.19525(18) 0.36873(11) 0.89322(9) 0.0242(3) Uani 1 1 d . . . . .
H1A H 0.105199 0.338261 0.889420 0.029 Uiso 1 1 calc R U . . .
H1B H 0.172909 0.434225 0.899893 0.029 Uiso 1 1 calc R U . . .
N2 N 0.50917(18) 0.36106(11) 0.89410(9) 0.0252(3) Uani 1 1 d . . . . .
H2A H 0.621282 0.325861 0.890881 0.030 Uiso 1 1 calc R U . . .
H2B H 0.487577 0.426530 0.900769 0.030 Uiso 1 1 calc R U . . .
N3 N 0.40390(18) 0.21359(11) 0.87852(10) 0.0291(3) Uani 1 1 d . . . . .
H3A H 0.516234 0.178698 0.875331 0.035 Uiso 1 1 calc R U . . .
H3B H 0.313811 0.182986 0.875035 0.035 Uiso 1 1 calc R U . . .
N4 N 0.77260(18) 1.14827(11) 0.09515(10) 0.0273(3) Uani 1 1 d . . . . .
H4A H 0.659368 1.183291 0.095883 0.033 Uiso 1 1 calc R U . . .
H4B H 0.797887 1.078145 0.098542 0.033 Uiso 1 1 calc R U . . .
N5 N 0.86853(19) 1.31057(11) 0.08356(10) 0.0288(3) Uani 1 1 d . . . . .
H5A H 0.956078 1.345713 0.080348 0.035 Uiso 1 1 calc R U . . .
H5B H 0.754987 1.345549 0.083395 0.035 Uiso 1 1 calc R U . . .
N6 N 1.08334(17) 1.14812(11) 0.08905(9) 0.0245(3) Uani 1 1 d . . . . .
H6A H 1.171322 1.182934 0.085848 0.029 Uiso 1 1 calc R U . . .
H6B H 1.108709 1.077996 0.092435 0.029 Uiso 1 1 calc R U . . .


_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 O1 1.4591(11) . ?
S1 O2 1.4634(10) . ?
S1 O3 1.4560(11) . ?
S1 C9 1.7697(14) . ?
S2 O4 1.4612(11) . ?
S2 O5 1.4622(10) . ?
S2 O6 1.4594(10) . ?
S2 C18 1.7665(14) . ?
O7 C1 1.365(2) . ?
O7 C8 1.425(2) . ?
O8 C7 1.215(2) . ?
C1 C2 1.399(2) . ?
C1 C6 1.394(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(2) . ?
C4 C5 1.397(2) . ?
C4 C7 1.471(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.383(2) . ?
C9 C14 1.385(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.393(2) . ?
C12 C13 1.397(2) . ?
C12 C15 1.488(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.401(2) . ?
C15 C20 1.399(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.384(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.390(2) . ?
C18 C19 1.387(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.386(2) . ?
C20 H20 0.9300 . ?
C21 N4 1.3298(19) . ?
C21 N5 1.3245(19) . ?
C21 N6 1.3259(19) . ?
C22 N1 1.335(2) . ?
C22 N2 1.3254(19) . ?
C22 N3 1.3238(19) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?

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 S1 O2 111.83(6) . . ?
O1 S1 C9 106.48(6) . . ?
O2 S1 C9 105.85(6) . . ?
O3 S1 O1 113.12(6) . . ?
O3 S1 O2 112.67(6) . . ?
O3 S1 C9 106.24(6) . . ?
O4 S2 O5 112.11(6) . . ?
O4 S2 C18 105.40(6) . . ?
O5 S2 C18 106.92(6) . . ?
O6 S2 O4 112.15(6) . . ?
O6 S2 O5 113.28(6) . . ?
O6 S2 C18 106.33(6) . . ?
C1 O7 C8 118.05(13) . . ?
O7 C1 C2 123.99(15) . . ?
O7 C1 C6 115.39(14) . . ?
C6 C1 C2 120.62(15) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.88(15) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.27(15) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 119.34(15) . . ?
C3 C4 C7 121.19(15) . . ?
C5 C4 C7 119.46(16) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.22(15) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.67(15) . . ?
C5 C6 H6 120.2 . . ?
O8 C7 C4 124.84(18) . . ?
O8 C7 H7 117.6 . . ?
C4 C7 H7 117.6 . . ?
O7 C8 H8A 109.5 . . ?
O7 C8 H8B 109.5 . . ?
O7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 S1 120.21(11) . . ?
C10 C9 C14 120.11(13) . . ?
C14 C9 S1 119.67(11) . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.04(14) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 121.04(14) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C13 117.71(13) . . ?
C11 C12 C15 120.94(13) . . ?
C13 C12 C15 121.34(13) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 C12 121.66(14) . . ?
C14 C13 H13 119.2 . . ?
C9 C14 H14 120.3 . . ?
C13 C14 C9 119.40(14) . . ?
C13 C14 H14 120.3 . . ?
C16 C15 C12 121.53(13) . . ?
C20 C15 C12 120.65(13) . . ?
C20 C15 C16 117.82(13) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.42(14) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.52(13) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 S2 119.87(11) . . ?
C19 C18 S2 119.60(11) . . ?
C19 C18 C17 120.31(13) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.72(14) . . ?
C20 C19 H19 120.1 . . ?
C15 C20 H20 119.4 . . ?
C19 C20 C15 121.21(14) . . ?
C19 C20 H20 119.4 . . ?
N5 C21 N4 119.65(13) . . ?
N5 C21 N6 120.31(13) . . ?
N6 C21 N4 120.03(13) . . ?
N2 C22 N1 120.37(14) . . ?
N3 C22 N1 119.95(13) . . ?
N3 C22 N2 119.68(14) . . ?
C22 N1 H1A 120.0 . . ?
C22 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C22 N2 H2A 120.0 . . ?
C22 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C22 N3 H3A 120.0 . . ?
C22 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C21 N4 H4A 120.0 . . ?
C21 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C21 N5 H5A 120.0 . . ?
C21 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C21 N6 H6A 120.0 . . ?
C21 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?

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 C9 C10 C11 -177.39(12) . . . . ?
S1 C9 C14 C13 177.64(12) . . . . ?
S2 C18 C19 C20 -175.26(11) . . . . ?
O1 S1 C9 C10 125.19(12) . . . . ?
O1 S1 C9 C14 -53.93(13) . . . . ?
O2 S1 C9 C10 6.03(14) . . . . ?
O2 S1 C9 C14 -173.08(12) . . . . ?
O3 S1 C9 C10 -113.97(12) . . . . ?
O3 S1 C9 C14 66.92(13) . . . . ?
O4 S2 C18 C17 -80.77(13) . . . . ?
O4 S2 C18 C19 93.79(12) . . . . ?
O5 S2 C18 C17 38.69(13) . . . . ?
O5 S2 C18 C19 -146.75(12) . . . . ?
O6 S2 C18 C17 160.00(11) . . . . ?
O6 S2 C18 C19 -25.44(13) . . . . ?
O7 C1 C2 C3 179.76(14) . . . . ?
O7 C1 C6 C5 -179.94(14) . . . . ?
C1 C2 C3 C4 0.8(2) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
C2 C3 C4 C5 -1.1(2) . . . . ?
C2 C3 C4 C7 177.80(15) . . . . ?
C3 C4 C5 C6 1.0(2) . . . . ?
C3 C4 C7 O8 -2.9(3) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C5 C4 C7 O8 176.05(17) . . . . ?
C6 C1 C2 C3 -0.2(2) . . . . ?
C7 C4 C5 C6 -178.00(15) . . . . ?
C8 O7 C1 C2 0.4(2) . . . . ?
C8 O7 C1 C6 -179.59(14) . . . . ?
C9 C10 C11 C12 -0.4(2) . . . . ?
C10 C9 C14 C13 -1.5(2) . . . . ?
C10 C11 C12 C13 -1.0(2) . . . . ?
C10 C11 C12 C15 177.85(14) . . . . ?
C11 C12 C13 C14 1.3(2) . . . . ?
C11 C12 C15 C16 15.6(2) . . . . ?
C11 C12 C15 C20 -163.59(14) . . . . ?
C12 C13 C14 C9 -0.1(2) . . . . ?
C12 C15 C16 C17 -179.77(13) . . . . ?
C12 C15 C20 C19 -179.80(13) . . . . ?
C13 C12 C15 C16 -165.54(14) . . . . ?
C13 C12 C15 C20 15.3(2) . . . . ?
C14 C9 C10 C11 1.7(2) . . . . ?
C15 C12 C13 C14 -177.59(14) . . . . ?
C15 C16 C17 C18 -0.5(2) . . . . ?
C16 C15 C20 C19 1.0(2) . . . . ?
C16 C17 C18 S2 175.66(11) . . . . ?
C16 C17 C18 C19 1.1(2) . . . . ?
C17 C18 C19 C20 -0.7(2) . . . . ?
C18 C19 C20 C15 -0.4(2) . . . . ?
C20 C15 C16 C17 -0.5(2) . . . . ?

_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 1.300
_oxdiff_exptl_absorpt_empirical_full_min 0.664
####################################################################### 
# 
# 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_c1b+i
_database_code_depnum_ccdc_archive 'CCDC 2152719'
loop_
_audit_author_name
_audit_author_address
'Shuqin Qin'
;Jinan University
China
;
_audit_update_record             
;
2022-02-17 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_audit_creation_date             2021-12-06
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 O6 S2, 3(C10 H12 O), 2(C H6 N3)'
_chemical_formula_sum            'C44 H56 N6 O9 S2'
_chemical_formula_weight         877.06
_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.6608(5)
_cell_length_b                   10.9150(7)
_cell_length_c                   27.573(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.659(7)
_cell_angle_gamma                90
_cell_volume                     2298.0(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3315
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      29.0820
_cell_measurement_theta_min      2.8310
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             932
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9072
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.383
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  82.00   1.00    5.00    --   11.74  37.00  60.00   88
  2  ω    -50.00  40.00   1.00    5.00    --   11.74 -57.00-120.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0325803000
_diffrn_orient_matrix_UB_12      -0.0602927000
_diffrn_orient_matrix_UB_13      -0.0024481000
_diffrn_orient_matrix_UB_21      0.0061518000
_diffrn_orient_matrix_UB_22      0.0101396000
_diffrn_orient_matrix_UB_23      -0.0252197000
_diffrn_orient_matrix_UB_31      0.0868251000
_diffrn_orient_matrix_UB_32      0.0218512000
_diffrn_orient_matrix_UB_33      0.0049701000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3409
_reflns_number_total             4031
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4031
_refine_ls_number_restraints     92
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0777
_refine_ls_restrained_S_all      1.179
_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)+(0.0301P)²+6.4266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1770
_refine_ls_wR_factor_ref         0.1823
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C4B-C8B
 1.5 with sigma of 0.02
 O1B-C7B
 1.45 with sigma of 0.02
 C8B-C9B
 1.33 with sigma of 0.02
 C9B-C10B
 1.52 with sigma of 0.02
 C1B-O1B
 1.48 with sigma of 0.02
 C5B-C4B \\sim C5B-C6B \\sim C6B-C1B \\sim C2B-C1B \\sim C2B-C3B \\sim C4B-C3B
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 O1B, C1B, C2B, C3B, C4B, C5B, C6B, C7B, C8B, C9B, C10B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Fixed Sof: O1B(0.5) C1B(0.5) C2B(0.5) H2B(0.5) C3B(0.5) H3B(0.5) C4B(0.5)
 C5B(0.5) H5B(0.5) C6B(0.5) H6B(0.5) C7B(0.5) H7BA(0.5) H7BB(0.5) H7BC(0.5)
 C8B(0.5) H8B(0.5) C9B(0.5) H9B(0.5) C10B(0.5) H10D(0.5) H10E(0.5) H10F(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C2A(H2A), C3A(H3A), C5A(H5A), C6A(H6A),
 C8A(H8A), C9A(H9A), C2B(H2B), C3B(H3B), C5B(H5B), C6B(H6B), C8B(H8B), C9B(H9B)
5.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2C,H2D), N3(H3C,H3D)
5.c Idealised Me refined as rotating group:
 C7A(H7AA,H7AB,H7AC), C10A(H10A,H10B,H10C), C7B(H7BA,H7BB,H7BC), C10B(H10D,
 H10E,H10F)
;
_atom_sites_solution_hydrogens   geom
_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 0.01830(12) -0.00701(9) 0.30806(3) 0.0212(3) Uani 1 1 d . . . . .
O1 O 0.1758(3) -0.0748(2) 0.29738(9) 0.0245(6) Uani 1 1 d . . . . .
O2 O 0.0171(4) 0.1187(3) 0.29048(10) 0.0282(7) Uani 1 1 d . . . . .
O3 O -0.1419(3) -0.0729(2) 0.29058(9) 0.0237(6) Uani 1 1 d . . . . .
O1A O 0.5921(4) 0.2989(3) 0.35140(11) 0.0404(8) Uani 1 1 d . . . . .
O1B O 0.0981(9) 0.5354(7) 0.3663(2) 0.0372(16) Uani 0.5 1 d D . P A -1
C1 C 0.0193(5) -0.0014(4) 0.37197(13) 0.0214(8) Uani 1 1 d . . . . .
C2 C -0.0671(7) 0.0913(4) 0.39419(16) 0.0441(13) Uani 1 1 d . . . . .
H2 H -0.120547 0.153736 0.375439 0.053 Uiso 1 1 calc R U . . .
C3 C -0.0748(7) 0.0921(4) 0.44380(16) 0.0459(14) Uani 1 1 d . . . . .
H3 H -0.132932 0.155719 0.458152 0.055 Uiso 1 1 calc R U . . .
C4 C 0.0028(5) -0.0007(4) 0.47320(13) 0.0226(8) Uani 1 1 d . . . . .
C5 C 0.0885(6) -0.0930(4) 0.44970(15) 0.0331(10) Uani 1 1 d . . . . .
H5 H 0.142237 -0.156096 0.468045 0.040 Uiso 1 1 calc R U . . .
C6 C 0.0958(6) -0.0934(4) 0.40026(15) 0.0332(10) Uani 1 1 d . . . . .
H6 H 0.153330 -0.156804 0.385626 0.040 Uiso 1 1 calc R U . . .
C7 C 0.5050(5) 0.1327(4) 0.25956(13) 0.0213(8) Uani 1 1 d . . . . .
C1A C 0.5616(6) 0.2817(4) 0.39936(16) 0.0318(10) Uani 1 1 d . . . . .
C2A C 0.4708(6) 0.1766(4) 0.41018(18) 0.0401(11) Uani 1 1 d . . . . .
H2A H 0.434193 0.122318 0.385426 0.048 Uiso 1 1 calc R U . . .
C3A C 0.4346(6) 0.1522(4) 0.45707(18) 0.0376(11) Uani 1 1 d . . . . .
H3A H 0.372849 0.081411 0.463460 0.045 Uiso 1 1 calc R U . . .
C4A C 0.4879(6) 0.2304(4) 0.49555(17) 0.0313(10) Uani 1 1 d . . . . .
C5A C 0.5793(5) 0.3344(4) 0.48460(15) 0.0276(9) Uani 1 1 d . . . . .
H5A H 0.616618 0.388036 0.509508 0.033 Uiso 1 1 calc R U . . .
C6A C 0.6174(5) 0.3611(4) 0.43686(15) 0.0289(9) Uani 1 1 d . . . . .
H6A H 0.679695 0.431545 0.430330 0.035 Uiso 1 1 calc R U . . .
C7A C 0.6866(7) 0.4047(5) 0.34006(17) 0.0496(14) Uani 1 1 d . . . . .
H7AA H 0.702080 0.405719 0.305864 0.074 Uiso 1 1 calc R U . . .
H7AB H 0.799100 0.404020 0.358155 0.074 Uiso 1 1 calc R U . . .
H7AC H 0.622956 0.476384 0.348462 0.074 Uiso 1 1 calc R U . . .
C8A C 0.4454(6) 0.2003(4) 0.54527(17) 0.0350(11) Uani 1 1 d . . . . .
H8A H 0.388380 0.126050 0.548841 0.042 Uiso 1 1 calc R U . . .
C9A C 0.4771(6) 0.2642(5) 0.58495(17) 0.0411(12) Uani 1 1 d . . . . .
H9A H 0.533217 0.339077 0.582100 0.049 Uiso 1 1 calc R U . . .
C10A C 0.4313(7) 0.2278(5) 0.63471(18) 0.0535(15) Uani 1 1 d . . . . .
H10A H 0.385943 0.145784 0.633750 0.080 Uiso 1 1 calc R U . . .
H10B H 0.344397 0.282843 0.645322 0.080 Uiso 1 1 calc R U . . .
H10C H 0.534280 0.231471 0.656963 0.080 Uiso 1 1 calc R U . . .
C1B C 0.0679(14) 0.5144(9) 0.4151(3) 0.0302(18) Uani 0.5 1 d D . P A -1
C2B C -0.0338(11) 0.6021(8) 0.4355(3) 0.0329(16) Uani 0.5 1 d D . P A -1
H2B H -0.077554 0.668482 0.417171 0.040 Uiso 0.5 1 calc R U P A -1
C3B C -0.0697(12) 0.5896(8) 0.4840(3) 0.0324(17) Uani 0.5 1 d D . P A -1
H3B H -0.134699 0.649863 0.498158 0.039 Uiso 0.5 1 calc R U P A -1
C4B C -0.0104(13) 0.4892(9) 0.5117(3) 0.0332(16) Uani 0.5 1 d D . P A -1
C5B C 0.0896(12) 0.4031(8) 0.4900(3) 0.0332(18) Uani 0.5 1 d D . P A -1
H5B H 0.130811 0.335681 0.508143 0.040 Uiso 0.5 1 calc R U P A -1
C6B C 0.1309(11) 0.4136(8) 0.4420(3) 0.0336(17) Uani 0.5 1 d D . P A -1
H6B H 0.199133 0.354639 0.428196 0.040 Uiso 0.5 1 calc R U P A -1
C7B C 0.197(2) 0.4414(14) 0.3435(4) 0.053(4) Uani 0.5 1 d D . P A -1
H7BA H 0.214373 0.465293 0.310669 0.079 Uiso 0.5 1 calc R U P A -1
H7BB H 0.134169 0.365385 0.343139 0.079 Uiso 0.5 1 calc R U P A -1
H7BC H 0.309077 0.431306 0.361424 0.079 Uiso 0.5 1 calc R U P A -1
C8B C -0.0476(14) 0.4719(11) 0.5636(4) 0.040(2) Uani 0.5 1 d D . P A -1
H8B H 0.000494 0.402708 0.579194 0.048 Uiso 0.5 1 calc R U P A -1
C9B C -0.1400(14) 0.5433(12) 0.5895(4) 0.049(2) Uani 0.5 1 d D . P A -1
H9B H -0.188848 0.613548 0.574972 0.059 Uiso 0.5 1 calc R U P A -1
C10B C -0.172(2) 0.5175(16) 0.6421(4) 0.060(4) Uani 0.5 1 d D . P A -1
H10D H -0.295016 0.506635 0.644802 0.090 Uiso 0.5 1 calc R U P A -1
H10E H -0.130270 0.585269 0.662022 0.090 Uiso 0.5 1 calc R U P A -1
H10F H -0.110445 0.444448 0.652729 0.090 Uiso 0.5 1 calc R U P A -1
N1 N 0.5118(4) 0.0274(3) 0.28393(12) 0.0288(8) Uani 1 1 d . . . . .
H1A H 0.417426 -0.004218 0.293348 0.035 Uiso 1 1 calc R U . . .
H1B H 0.610534 -0.009013 0.290275 0.035 Uiso 1 1 calc R U . . .
N2 N 0.6508(4) 0.1790(3) 0.24400(12) 0.0268(8) Uani 1 1 d . . . . .
H2C H 0.646799 0.245874 0.227462 0.032 Uiso 1 1 calc R U . . .
H2D H 0.749092 0.142103 0.250472 0.032 Uiso 1 1 calc R U . . .
N3 N 0.3530(4) 0.1888(3) 0.24978(12) 0.0260(8) Uani 1 1 d . . . . .
H3C H 0.348182 0.255737 0.233253 0.031 Uiso 1 1 calc R U . . .
H3D H 0.259030 0.158395 0.259949 0.031 Uiso 1 1 calc R U . . .


_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 O1 1.465(3) . ?
S1 O2 1.455(3) . ?
S1 O3 1.470(3) . ?
S1 C1 1.763(4) . ?
O1A C1A 1.374(5) . ?
O1A C7A 1.411(6) . ?
O1B C1B 1.401(10) . ?
O1B C7B 1.451(11) . ?
C1 C2 1.379(6) . ?
C1 C6 1.374(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.400(6) . ?
C4 C4 1.482(7) 3_556 ?
C4 C5 1.392(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.369(6) . ?
C6 H6 0.9300 . ?
C7 N1 1.330(5) . ?
C7 N2 1.329(5) . ?
C7 N3 1.324(5) . ?
C1A C2A 1.387(6) . ?
C1A C6A 1.390(6) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.370(7) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.397(6) . ?
C4A C5A 1.380(6) . ?
C4A C8A 1.472(6) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.402(6) . ?
C6A H6A 0.9300 . ?
C7A H7AA 0.9600 . ?
C7A H7AB 0.9600 . ?
C7A H7AC 0.9600 . ?
C8A H8A 0.9300 . ?
C8A C9A 1.303(7) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.497(6) . ?
C10A H10A 0.9600 . ?
C10A H10B 0.9600 . ?
C10A H10C 0.9600 . ?
C1B C2B 1.383(11) . ?
C1B C6B 1.391(10) . ?
C2B H2B 0.9300 . ?
C2B C3B 1.393(10) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.391(10) . ?
C4B C5B 1.379(10) . ?
C4B C8B 1.495(11) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.391(10) . ?
C6B H6B 0.9300 . ?
C7B H7BA 0.9600 . ?
C7B H7BB 0.9600 . ?
C7B H7BC 0.9600 . ?
C8B H8B 0.9300 . ?
C8B C9B 1.303(12) . ?
C9B H9B 0.9300 . ?
C9B C10B 1.516(13) . ?
C10B H10D 0.9600 . ?
C10B H10E 0.9600 . ?
C10B H10F 0.9600 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2C 0.8600 . ?
N2 H2D 0.8600 . ?
N3 H3C 0.8600 . ?
N3 H3D 0.8600 . ?

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 S1 O3 111.48(16) . . ?
O1 S1 C1 106.37(17) . . ?
O2 S1 O1 113.10(16) . . ?
O2 S1 O3 111.70(17) . . ?
O2 S1 C1 107.43(17) . . ?
O3 S1 C1 106.29(16) . . ?
C1A O1A C7A 117.1(3) . . ?
C1B O1B C7B 115.8(8) . . ?
C2 C1 S1 120.4(3) . . ?
C6 C1 S1 120.6(3) . . ?
C6 C1 C2 118.8(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.4(4) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C4 121.7(4) . 3_556 ?
C5 C4 C3 116.7(4) . . ?
C5 C4 C4 121.6(4) . 3_556 ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.6(4) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.9(4) . . ?
C5 C6 H6 119.6 . . ?
N2 C7 N1 119.5(4) . . ?
N3 C7 N1 120.0(4) . . ?
N3 C7 N2 120.4(3) . . ?
O1A C1A C2A 116.6(4) . . ?
O1A C1A C6A 124.4(4) . . ?
C2A C1A C6A 119.0(4) . . ?
C1A C2A H2A 119.7 . . ?
C3A C2A C1A 120.5(4) . . ?
C3A C2A H2A 119.7 . . ?
C2A C3A H3A 119.0 . . ?
C2A C3A C4A 121.9(4) . . ?
C4A C3A H3A 119.0 . . ?
C3A C4A C8A 119.9(4) . . ?
C5A C4A C3A 117.3(4) . . ?
C5A C4A C8A 122.8(4) . . ?
C4A C5A H5A 119.2 . . ?
C4A C5A C6A 121.7(4) . . ?
C6A C5A H5A 119.2 . . ?
C1A C6A C5A 119.6(4) . . ?
C1A C6A H6A 120.2 . . ?
C5A C6A H6A 120.2 . . ?
O1A C7A H7AA 109.5 . . ?
O1A C7A H7AB 109.5 . . ?
O1A C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
C4A C8A H8A 115.7 . . ?
C9A C8A C4A 128.5(4) . . ?
C9A C8A H8A 115.7 . . ?
C8A C9A H9A 117.1 . . ?
C8A C9A C10A 125.9(5) . . ?
C10A C9A H9A 117.1 . . ?
C9A C10A H10A 109.5 . . ?
C9A C10A H10B 109.5 . . ?
C9A C10A H10C 109.5 . . ?
H10A C10A H10B 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C2B C1B O1B 114.8(7) . . ?
C2B C1B C6B 120.8(9) . . ?
C6B C1B O1B 124.3(9) . . ?
C1B C2B H2B 120.5 . . ?
C1B C2B C3B 119.0(9) . . ?
C3B C2B H2B 120.5 . . ?
C2B C3B H3B 119.2 . . ?
C4B C3B C2B 121.5(9) . . ?
C4B C3B H3B 119.2 . . ?
C3B C4B C8B 123.1(9) . . ?
C5B C4B C3B 117.9(7) . . ?
C5B C4B C8B 119.0(8) . . ?
C4B C5B H5B 118.9 . . ?
C4B C5B C6B 122.2(8) . . ?
C6B C5B H5B 118.9 . . ?
C1B C6B C5B 118.5(8) . . ?
C1B C6B H6B 120.7 . . ?
C5B C6B H6B 120.7 . . ?
O1B C7B H7BA 109.5 . . ?
O1B C7B H7BB 109.5 . . ?
O1B C7B H7BC 109.5 . . ?
H7BA C7B H7BB 109.5 . . ?
H7BA C7B H7BC 109.5 . . ?
H7BB C7B H7BC 109.5 . . ?
C4B C8B H8B 116.4 . . ?
C9B C8B C4B 127.1(10) . . ?
C9B C8B H8B 116.4 . . ?
C8B C9B H9B 118.3 . . ?
C8B C9B C10B 123.4(12) . . ?
C10B C9B H9B 118.3 . . ?
C9B C10B H10D 109.5 . . ?
C9B C10B H10E 109.5 . . ?
C9B C10B H10F 109.5 . . ?
H10D C10B H10E 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C7 N1 H1A 120.0 . . ?
C7 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C7 N2 H2C 120.0 . . ?
C7 N2 H2D 120.0 . . ?
H2C N2 H2D 120.0 . . ?
C7 N3 H3C 120.0 . . ?
C7 N3 H3D 120.0 . . ?
H3C N3 H3D 120.0 . . ?

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 C1 C2 C3 176.3(4) . . . . ?
S1 C1 C6 C5 -176.3(4) . . . . ?
O1 S1 C1 C2 154.9(4) . . . . ?
O1 S1 C1 C6 -29.5(4) . . . . ?
O2 S1 C1 C2 33.5(4) . . . . ?
O2 S1 C1 C6 -150.9(3) . . . . ?
O3 S1 C1 C2 -86.2(4) . . . . ?
O3 S1 C1 C6 89.4(4) . . . . ?
O1A C1A C2A C3A -180.0(4) . . . . ?
O1A C1A C6A C5A -179.9(4) . . . . ?
O1B C1B C2B C3B -179.4(8) . . . . ?
O1B C1B C6B C5B -179.3(9) . . . . ?
C1 C2 C3 C4 -0.5(9) . . . . ?
C2 C1 C6 C5 -0.7(7) . . . . ?
C2 C3 C4 C4 179.1(5) . . . 3_556 ?
C2 C3 C4 C5 0.3(8) . . . . ?
C3 C4 C5 C6 -0.3(7) . . . . ?
C4 C4 C5 C6 -179.1(5) 3_556 . . . ?
C4 C5 C6 C1 0.5(7) . . . . ?
C6 C1 C2 C3 0.7(8) . . . . ?
C1A C2A C3A C4A -0.4(7) . . . . ?
C2A C1A C6A C5A -0.7(6) . . . . ?
C2A C3A C4A C5A 0.0(7) . . . . ?
C2A C3A C4A C8A 179.8(4) . . . . ?
C3A C4A C5A C6A 0.1(6) . . . . ?
C3A C4A C8A C9A -176.7(5) . . . . ?
C4A C5A C6A C1A 0.3(6) . . . . ?
C4A C8A C9A C10A -179.5(5) . . . . ?
C5A C4A C8A C9A 3.1(7) . . . . ?
C6A C1A C2A C3A 0.8(7) . . . . ?
C7A O1A C1A C2A -179.1(4) . . . . ?
C7A O1A C1A C6A 0.0(7) . . . . ?
C8A C4A C5A C6A -179.7(4) . . . . ?
C1B C2B C3B C4B -2.1(15) . . . . ?
C2B C1B C6B C5B -0.1(14) . . . . ?
C2B C3B C4B C5B 1.7(16) . . . . ?
C2B C3B C4B C8B -179.4(10) . . . . ?
C3B C4B C5B C6B -0.4(17) . . . . ?
C3B C4B C8B C9B 1.6(19) . . . . ?
C4B C5B C6B C1B -0.4(15) . . . . ?
C4B C8B C9B C10B 179.5(12) . . . . ?
C5B C4B C8B C9B -179.5(11) . . . . ?
C6B C1B C2B C3B 1.3(14) . . . . ?
C7B O1B C1B C2B -177.1(11) . . . . ?
C7B O1B C1B C6B 2.1(16) . . . . ?
C8B C4B C5B C6B -179.4(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.726
_oxdiff_exptl_absorpt_empirical_full_min 0.473
####################################################################### 
# 
# 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-l_3_sq
_database_code_depnum_ccdc_archive 'CCDC 2152722'
loop_
_audit_author_name
_audit_author_address
'Shuqin Qin'
;Jinan University
China
;
_audit_update_record             
;
2022-02-17 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_audit_creation_date             2021-12-13
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C6 H4 O3 S), C10 H18 O, 2(C H6 N3)'
_chemical_formula_sum            'C24 H39 N6 O7 S2'
_chemical_formula_weight         587.73
_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 0.0181 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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   39.275(9)
_cell_length_b                   12.1367(13)
_cell_length_c                   7.3230(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3490.7(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1287
_cell_measurement_temperature    99.97(14)
_cell_measurement_theta_max      62.5290
_cell_measurement_theta_min      3.7770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.752
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.118
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1252
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.1166
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8655
_diffrn_reflns_point_group_measured_fraction_full 0.904
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.356
_diffrn_reflns_theta_min         3.812
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  69.00   1.00    8.00    --   40.73 -57.00  30.00   90
  2  ω     29.00  82.00   1.00    8.00    --   40.73 -99.00 -30.00   53
  3  ω     76.00 127.00   1.00   10.00    --  107.58 -45.00   0.00   51
  4  ω     79.00 158.00   1.00   10.00    --  107.58  30.00-120.00   79
  5  ω     37.00 111.00   1.00   10.00    --  107.58-125.00 -60.00   74
  6  ω    111.00 176.00   1.00   10.00    --  107.58  45.00 150.00   65
  7  ω    -74.00 -40.00   1.00    8.00    --  -40.73 125.00 120.00   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1879210000
_diffrn_orient_matrix_UB_12      -0.0115214000
_diffrn_orient_matrix_UB_13      0.0431439000
_diffrn_orient_matrix_UB_21      -0.0417272000
_diffrn_orient_matrix_UB_22      0.0367358000
_diffrn_orient_matrix_UB_23      0.0366782000
_diffrn_orient_matrix_UB_31      -0.0849510000
_diffrn_orient_matrix_UB_32      0.0074606000
_diffrn_orient_matrix_UB_33      -0.1135997000
_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'
_reflns_Friedel_coverage         0.559
_reflns_Friedel_fraction_full    0.779
_reflns_Friedel_fraction_max     0.712
_reflns_number_gt                4200
_reflns_number_total             6067
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.897
_refine_diff_density_rms         0.142
_refine_ls_abs_structure_details 
;
 Flack x determined using 828 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         6067
_refine_ls_number_restraints     88
_refine_ls_R_factor_all          0.1755
_refine_ls_R_factor_gt           0.1514
_refine_ls_restrained_S_all      1.062
_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)+(0.1680P)²+26.7792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3810
_refine_ls_wR_factor_ref         0.4012
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid bond restraints
 C19, C20
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C23, C22
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C7, C8
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 S1, O2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C23 \\sim C22: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
C7 \\sim C8: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
C19 \\sim C20: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
S1 \\sim O2: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
Uanis(C19) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C16)
\\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C11) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C3) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C21) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(O4) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(N4) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C15) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
4.a Rotating group:
 N5(H5C,H5D)
4.b Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C1(H1)
4.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B)
4.d Aromatic/amide H refined with riding coordinates:
 C24(H24), C23(H23), C21(H21), C20(H20), C15(H15), C14(H14), C18(H18), C17(H17)
4.e X=CH2 refined with riding coordinates:
 C8(H8A,H8B), N1(H1A,H1B), N2(H2A,H2B), N3(H3C,H3D), N4(H4A,H4B), N6(H6C,H6D)
4.f Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C9(H9A,H9B,H9C)
4.g Idealised tetrahedral OH refined as rotating group:
 O7(H7)
;
_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 0.39257(13) 0.2384(3) -0.1054(5) 0.0566(12) Uani 1 1 d . U . . .
S2 S 0.38051(11) 0.6994(3) 0.4315(4) 0.0410(9) Uani 1 1 d . . . . .
O1 O 0.3954(3) 0.1682(9) -0.2688(17) 0.058(3) Uani 1 1 d . . . . .
O2 O 0.3622(3) 0.3066(8) -0.1055(14) 0.057(2) Uani 1 1 d . U . . .
O3 O 0.3953(3) 0.1737(8) 0.0579(15) 0.057(3) Uani 1 1 d . . . . .
O4 O 0.3591(3) 0.6679(8) 0.2780(13) 0.040(2) Uani 1 1 d . U . . .
O5 O 0.3674(3) 0.6577(9) 0.6083(13) 0.047(3) Uani 1 1 d . . . . .
O6 O 0.3869(3) 0.8190(8) 0.4353(16) 0.053(3) Uani 1 1 d . . . . .
O7 O 0.2985(3) 0.5675(10) 0.3717(17) 0.057(3) Uani 1 1 d . . . . .
H7 H 0.312592 0.606100 0.319257 0.086 Uiso 1 1 calc R U . . .
C19 C 0.4274(5) 0.3284(15) -0.108(3) 0.061(3) Uani 1 1 d . U . . .
C24 C 0.4231(5) 0.4356(17) -0.157(3) 0.067(5) Uani 1 1 d . U . . .
H24 H 0.401930 0.462697 -0.191381 0.080 Uiso 1 1 calc R U . . .
C23 C 0.4527(5) 0.5057(17) -0.152(3) 0.064(3) Uani 1 1 d . U . . .
H23 H 0.450122 0.580313 -0.177691 0.077 Uiso 1 1 calc R U . . .
C22 C 0.4846(5) 0.4660(16) -0.112(3) 0.064(3) Uani 1 1 d . U . . .
C21 C 0.4885(5) 0.3526(16) -0.064(3) 0.064(5) Uani 1 1 d . U . . .
H21 H 0.509948 0.324266 -0.037246 0.077 Uiso 1 1 calc R U . . .
C20 C 0.4595(5) 0.2844(16) -0.059(3) 0.061(3) Uani 1 1 d . U . . .
H20 H 0.461463 0.211127 -0.023071 0.073 Uiso 1 1 calc R U . . .
C15 C 0.4532(4) 0.4763(14) 0.344(2) 0.045(4) Uani 1 1 d . U . . .
H15 H 0.454090 0.403210 0.305792 0.054 Uiso 1 1 calc R U . . .
C14 C 0.4221(4) 0.5260(12) 0.3577(19) 0.043(4) Uani 1 1 d . . . . .
H14 H 0.402271 0.486500 0.335259 0.052 Uiso 1 1 calc R U . . .
C13 C 0.4206(4) 0.6393(14) 0.407(2) 0.052(4) Uani 1 1 d . . . . .
C18 C 0.4503(4) 0.6936(11) 0.4395(19) 0.042(3) Uani 1 1 d . . . . .
H18 H 0.449723 0.768898 0.462416 0.050 Uiso 1 1 calc R U . . .
C17 C 0.4816(5) 0.6392(13) 0.439(2) 0.050(4) Uani 1 1 d . . . . .
H17 H 0.501239 0.675702 0.475783 0.060 Uiso 1 1 calc R U . . .
C16 C 0.4830(3) 0.5290(11) 0.3830(19) 0.037(3) Uani 1 1 d . U . . .
C11 C 0.3451(4) 0.3411(14) 0.399(3) 0.052(4) Uani 1 1 d . U . . .
C12 C 0.3834(4) 0.8778(11) 0.930(2) 0.043(3) Uani 1 1 d . . . . .
C2 C 0.2652(4) 0.6103(13) 0.340(2) 0.044(4) Uiso 1 1 d . . . . .
H2 H 0.264959 0.689060 0.369688 0.053 Uiso 1 1 calc R U . . .
C3 C 0.2417(4) 0.5487(14) 0.472(2) 0.049(4) Uani 1 1 d . U . . .
H3A H 0.245072 0.470070 0.455976 0.059 Uiso 1 1 calc R U . . .
H3B H 0.247932 0.567287 0.595908 0.059 Uiso 1 1 calc R U . . .
C4 C 0.2046(5) 0.5748(16) 0.444(3) 0.072(6) Uani 1 1 d . . . . .
H4 H 0.201825 0.651846 0.480655 0.087 Uiso 1 1 calc R U . . .
C10 C 0.1808(5) 0.5089(16) 0.566(3) 0.069(5) Uani 1 1 d . . . . .
H10A H 0.184041 0.431619 0.544308 0.104 Uiso 1 1 calc R U . . .
H10B H 0.157640 0.528464 0.540075 0.104 Uiso 1 1 calc R U . . .
H10C H 0.185781 0.525074 0.691792 0.104 Uiso 1 1 calc R U . . .
C5 C 0.1945(5) 0.5708(15) 0.240(3) 0.058(5) Uani 1 1 d . . . . .
H5A H 0.194213 0.494580 0.199678 0.070 Uiso 1 1 calc R U . . .
H5B H 0.171605 0.599767 0.226195 0.070 Uiso 1 1 calc R U . . .
C6 C 0.2178(5) 0.6342(18) 0.121(4) 0.084(7) Uani 1 1 d . . . . .
H6A H 0.215970 0.711995 0.149411 0.101 Uiso 1 1 calc R U . . .
H6B H 0.211383 0.623904 -0.005748 0.101 Uiso 1 1 calc R U . . .
C1 C 0.2554(4) 0.5954(15) 0.1495(19) 0.051(4) Uani 1 1 d . . . . .
H1 H 0.255973 0.516046 0.124791 0.061 Uiso 1 1 calc R U . . .
C7 C 0.2796(6) 0.651(2) 0.009(2) 0.081(5) Uani 1 1 d . U . . .
C8 C 0.2974(6) 0.587(2) -0.105(2) 0.083(5) Uani 1 1 d . U . . .
H8A H 0.314344 0.617992 -0.178156 0.099 Uiso 1 1 calc R U . . .
H8B H 0.292941 0.512214 -0.111264 0.099 Uiso 1 1 calc R U . . .
C9 C 0.2843(7) 0.776(2) 0.032(5) 0.137(14) Uani 1 1 d . . . . .
H9A H 0.262440 0.810947 0.036985 0.205 Uiso 1 1 calc R U . . .
H9B H 0.297025 0.804383 -0.069334 0.205 Uiso 1 1 calc R U . . .
H9C H 0.296465 0.790000 0.143389 0.205 Uiso 1 1 calc R U . . .
N1 N 0.3337(4) 0.3782(11) 0.2320(18) 0.056(4) Uani 1 1 d . . . . .
H1A H 0.318571 0.429216 0.226648 0.067 Uiso 1 1 calc R U . . .
H1B H 0.341810 0.350326 0.133131 0.067 Uiso 1 1 calc R U . . .
N2 N 0.3676(4) 0.2582(9) 0.4006(16) 0.061(4) Uani 1 1 d . . . . .
H2A H 0.374404 0.231120 0.502740 0.073 Uiso 1 1 calc R U . . .
H2B H 0.375195 0.232015 0.299380 0.073 Uiso 1 1 calc R U . . .
N3 N 0.3329(4) 0.3832(12) 0.5509(17) 0.062(4) Uani 1 1 d . . . . .
H3C H 0.339302 0.357569 0.654744 0.075 Uiso 1 1 calc R U . . .
H3D H 0.318435 0.436463 0.546326 0.075 Uiso 1 1 calc R U . . .
N4 N 0.3888(3) 0.9322(10) 0.7747(17) 0.044(3) Uani 1 1 d . U . . .
H4A H 0.389326 0.897076 0.672719 0.053 Uiso 1 1 calc R U . . .
H4B H 0.391752 1.002420 0.776277 0.053 Uiso 1 1 calc R U . . .
N5 N 0.3843(4) 0.9349(10) 1.0907(14) 0.059(4) Uani 1 1 d . . . . .
H5C H 0.377334 1.001626 1.072961 0.071 Uiso 1 1 d R U . . .
H5D H 0.371125 0.903400 1.169298 0.071 Uiso 1 1 d R U . . .
N6 N 0.3787(4) 0.7710(7) 0.9408(16) 0.049(3) Uani 1 1 d . . . . .
H6C H 0.378913 0.731593 0.843219 0.059 Uiso 1 1 calc R U . . .
H6D H 0.375286 0.740445 1.045164 0.059 Uiso 1 1 calc R U . . .


_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 O1 1.473(12) . ?
S1 O2 1.451(13) . ?
S1 O3 1.435(12) . ?
S1 C19 1.749(19) . ?
S2 O4 1.455(10) . ?
S2 O5 1.482(9) . ?
S2 O6 1.473(10) . ?
S2 C13 1.744(17) . ?
O7 H7 0.8200 . ?
O7 C2 1.425(19) . ?
C19 C24 1.36(3) . ?
C19 C20 1.42(3) . ?
C24 H24 0.9300 . ?
C24 C23 1.44(3) . ?
C23 H23 0.9300 . ?
C23 C22 1.37(3) . ?
C22 C22 1.47(4) 2_665 ?
C22 C21 1.43(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.41(2) . ?
C20 H20 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.37(2) . ?
C15 C16 1.36(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.42(2) . ?
C13 C18 1.36(2) . ?
C18 H18 0.9300 . ?
C18 C17 1.39(2) . ?
C17 H17 0.9300 . ?
C17 C16 1.40(2) . ?
C16 C16 1.51(3) 2_665 ?
C11 N1 1.38(2) . ?
C11 N2 1.34(2) . ?
C11 N3 1.31(2) . ?
C12 N4 1.335(19) . ?
C12 N5 1.364(19) . ?
C12 N6 1.311(16) . ?
C2 H2 0.9800 . ?
C2 C3 1.53(2) . ?
C2 C1 1.46(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.51(3) . ?
C4 H4 0.9800 . ?
C4 C10 1.52(2) . ?
C4 C5 1.55(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.48(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C1 1.56(3) . ?
C1 H1 0.9800 . ?
C1 C7 1.56(3) . ?
C7 C8 1.34(3) . ?
C7 C9 1.53(3) . ?
C8 H8A 0.9300 . ?
C8 H8B 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 H3C 0.8600 . ?
N3 H3D 0.8600 . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 H5C 0.8641 . ?
N5 H5D 0.8630 . ?
N6 H6C 0.8600 . ?
N6 H6D 0.8600 . ?

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 S1 C19 106.9(9) . . ?
O2 S1 O1 113.1(7) . . ?
O2 S1 C19 106.6(8) . . ?
O3 S1 O1 110.8(6) . . ?
O3 S1 O2 111.9(7) . . ?
O3 S1 C19 107.1(9) . . ?
O4 S2 O5 112.7(6) . . ?
O4 S2 O6 111.9(7) . . ?
O4 S2 C13 109.4(7) . . ?
O5 S2 C13 105.0(7) . . ?
O6 S2 O5 112.3(6) . . ?
O6 S2 C13 105.1(8) . . ?
C2 O7 H7 109.5 . . ?
C24 C19 S1 120.4(15) . . ?
C24 C19 C20 122.4(18) . . ?
C20 C19 S1 117.2(14) . . ?
C19 C24 H24 121.3 . . ?
C19 C24 C23 117.5(19) . . ?
C23 C24 H24 121.3 . . ?
C24 C23 H23 118.9 . . ?
C22 C23 C24 122.2(19) . . ?
C22 C23 H23 118.9 . . ?
C23 C22 C22 124(2) . 2_665 ?
C23 C22 C21 119.3(18) . . ?
C21 C22 C22 117(2) . 2_665 ?
C22 C21 H21 120.5 . . ?
C20 C21 C22 119.0(18) . . ?
C20 C21 H21 120.5 . . ?
C19 C20 H20 120.3 . . ?
C21 C20 C19 119.4(17) . . ?
C21 C20 H20 120.3 . . ?
C14 C15 H15 118.5 . . ?
C16 C15 H15 118.5 . . ?
C16 C15 C14 122.9(15) . . ?
C15 C14 H14 120.5 . . ?
C15 C14 C13 119.0(15) . . ?
C13 C14 H14 120.5 . . ?
C14 C13 S2 118.0(13) . . ?
C18 C13 S2 123.6(13) . . ?
C18 C13 C14 118.4(15) . . ?
C13 C18 H18 119.1 . . ?
C13 C18 C17 121.8(14) . . ?
C17 C18 H18 119.1 . . ?
C18 C17 H17 120.4 . . ?
C18 C17 C16 119.1(14) . . ?
C16 C17 H17 120.4 . . ?
C15 C16 C17 118.5(14) . . ?
C15 C16 C16 122.8(16) . 2_665 ?
C17 C16 C16 118.6(15) . 2_665 ?
N2 C11 N1 117.8(16) . . ?
N3 C11 N1 120.4(15) . . ?
N3 C11 N2 121.7(16) . . ?
N4 C12 N5 118.7(11) . . ?
N6 C12 N4 124.1(14) . . ?
N6 C12 N5 117.1(13) . . ?
O7 C2 H2 109.3 . . ?
O7 C2 C3 105.9(13) . . ?
O7 C2 C1 110.7(13) . . ?
C3 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
C1 C2 C3 112.4(13) . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 C2 113.4(15) . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C3 C4 H4 105.7 . . ?
C3 C4 C10 113.7(19) . . ?
C3 C4 C5 111.9(14) . . ?
C10 C4 H4 105.7 . . ?
C10 C4 C5 113.3(16) . . ?
C5 C4 H4 105.7 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C5 H5A 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 C4 113.1(17) . . ?
C6 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C5 C6 C1 110.5(18) . . ?
H6A C6 H6B 108.1 . . ?
C1 C6 H6A 109.6 . . ?
C1 C6 H6B 109.6 . . ?
C2 C1 C6 109.9(16) . . ?
C2 C1 H1 107.0 . . ?
C2 C1 C7 114.7(15) . . ?
C6 C1 H1 107.0 . . ?
C7 C1 C6 110.8(16) . . ?
C7 C1 H1 107.0 . . ?
C8 C7 C1 119(2) . . ?
C8 C7 C9 125(2) . . ?
C9 C7 C1 116(2) . . ?
C7 C8 H8A 120.0 . . ?
C7 C8 H8B 120.0 . . ?
H8A C8 H8B 120.0 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 N1 H1A 120.0 . . ?
C11 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C11 N2 H2A 120.0 . . ?
C11 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C11 N3 H3C 120.0 . . ?
C11 N3 H3D 120.0 . . ?
H3C N3 H3D 120.0 . . ?
C12 N4 H4A 120.0 . . ?
C12 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C12 N5 H5C 109.8 . . ?
C12 N5 H5D 109.4 . . ?
H5C N5 H5D 109.1 . . ?
C12 N6 H6C 120.0 . . ?
C12 N6 H6D 120.0 . . ?
H6C N6 H6D 120.0 . . ?

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 C19 C24 C23 178.6(14) . . . . ?
S1 C19 C20 C21 178.2(15) . . . . ?
S2 C13 C18 C17 172.3(12) . . . . ?
O1 S1 C19 C24 104.4(18) . . . . ?
O1 S1 C19 C20 -75.6(17) . . . . ?
O2 S1 C19 C24 -16.9(19) . . . . ?
O2 S1 C19 C20 163.1(14) . . . . ?
O3 S1 C19 C24 -136.8(17) . . . . ?
O3 S1 C19 C20 43.2(17) . . . . ?
O4 S2 C13 C14 -45.8(15) . . . . ?
O4 S2 C13 C18 136.9(14) . . . . ?
O5 S2 C13 C14 75.4(14) . . . . ?
O5 S2 C13 C18 -101.9(15) . . . . ?
O6 S2 C13 C14 -166.0(13) . . . . ?
O6 S2 C13 C18 16.7(17) . . . . ?
O7 C2 C3 C4 -173.9(13) . . . . ?
O7 C2 C1 C6 175.5(14) . . . . ?
O7 C2 C1 C7 -59(2) . . . . ?
C19 C24 C23 C22 4(3) . . . . ?
C24 C19 C20 C21 -2(3) . . . . ?
C24 C23 C22 C22 177.9(14) . . . 2_665 ?
C24 C23 C22 C21 -3(3) . . . . ?
C23 C22 C21 C20 0(3) . . . . ?
C22 C22 C21 C20 178.8(14) 2_665 . . . ?
C22 C21 C20 C19 3(3) . . . . ?
C20 C19 C24 C23 -1(3) . . . . ?
C15 C14 C13 S2 -177.8(12) . . . . ?
C15 C14 C13 C18 0(2) . . . . ?
C14 C15 C16 C17 0(2) . . . . ?
C14 C15 C16 C16 174.6(11) . . . 2_665 ?
C14 C13 C18 C17 -5(2) . . . . ?
C13 C18 C17 C16 8(2) . . . . ?
C18 C17 C16 C15 -5(2) . . . . ?
C18 C17 C16 C16 179.9(11) . . . 2_665 ?
C16 C15 C14 C13 3(2) . . . . ?
C2 C3 C4 C10 176.7(15) . . . . ?
C2 C3 C4 C5 47(2) . . . . ?
C2 C1 C7 C8 114(2) . . . . ?
C2 C1 C7 C9 -57(3) . . . . ?
C3 C2 C1 C6 57.3(19) . . . . ?
C3 C2 C1 C7 -177.1(16) . . . . ?
C3 C4 C5 C6 -49(2) . . . . ?
C4 C5 C6 C1 55(2) . . . . ?
C10 C4 C5 C6 -179.5(17) . . . . ?
C5 C6 C1 C2 -59(2) . . . . ?
C5 C6 C1 C7 173.1(18) . . . . ?
C6 C1 C7 C8 -121(2) . . . . ?
C6 C1 C7 C9 68(2) . . . . ?
C1 C2 C3 C4 -52.9(19) . . . . ?

_platon_squeeze_details          ?
_platon_squeeze_special_details  ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.500 -0.085 263 72 '4 MeOH'
2 0.500 0.000 0.010 263 71 '4 MeOH'
3 0.261 0.281 0.315 17 1 '2 H2O'
4 0.739 0.719 0.315 18 1 ' '
5 0.239 0.781 0.684 17 0 '2 H2O'
6 0.761 0.218 0.684 17 0 '2 H2O'

_platon_squeeze_void_probe_radius 1.20
_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 1.335
_oxdiff_exptl_absorpt_empirical_full_min 0.760
####################################################################### 
# 
# 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_b-bpdsg
_database_code_depnum_ccdc_archive 'CCDC 2152720'
loop_
_audit_author_name
_audit_author_address
'Shuqin Qin'
;Jinan University
China
;
_audit_update_record             
;
2022-02-17 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_audit_creation_date             2021-12-09
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 O6 S2, 2(C H4 O), 2(C H6 N3)'
_chemical_formula_sum            'C16 H28 N6 O8 S2'
_chemical_formula_weight         496.56
_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                   11.9900(9)
_cell_length_b                   26.883(2)
_cell_length_c                   7.3973(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.394(7)
_cell_angle_gamma                90
_cell_volume                     2382.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2646
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      25.8520
_cell_measurement_theta_min      2.3010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0709
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10587
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.277
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  28.00   1.00    4.00    --  -11.27 -99.00 120.00   47
  2  ω     -8.00  82.00   1.00    4.00    --   11.90  77.00-150.00   90
  3  ω    -19.00  41.00   1.00    4.00    --   11.90 -77.00 -30.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0374482000
_diffrn_orient_matrix_UB_12      -0.0088386000
_diffrn_orient_matrix_UB_13      -0.0643978000
_diffrn_orient_matrix_UB_21      -0.0284603000
_diffrn_orient_matrix_UB_22      -0.0231073000
_diffrn_orient_matrix_UB_23      -0.0034138000
_diffrn_orient_matrix_UB_31      -0.0359622000
_diffrn_orient_matrix_UB_32      0.0091161000
_diffrn_orient_matrix_UB_33      -0.0711813000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3136
_reflns_number_total             4195
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0613
_refine_ls_restrained_S_all      1.050
_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)+(0.0526P)²+3.2184P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1364
_refine_ls_wR_factor_ref         0.1501
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12)
2.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), N3(H3A,H3B), N4(H4A,H4B), N5(H5A,H5B), N6(H6A,H6B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
2.d Idealised tetrahedral OH refined as rotating group:
 O7(H7), O8(H8A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.60195(8) 0.43052(4) 0.50357(11) 0.0226(3) Uani 1 1 d . . . . .
S2 S 1.05150(8) 0.09086(4) 0.46404(12) 0.0224(2) Uani 1 1 d . . . . .
O1 O 0.6841(2) 0.47055(9) 0.5115(3) 0.0245(6) Uani 1 1 d . . . . .
O2 O 0.5353(2) 0.42931(10) 0.6639(3) 0.0273(6) Uani 1 1 d . . . . .
O3 O 0.5332(2) 0.43107(10) 0.3362(3) 0.0274(6) Uani 1 1 d . . . . .
O4 O 1.0145(2) 0.06813(10) 0.2926(3) 0.0273(6) Uani 1 1 d . . . . .
O5 O 1.0189(2) 0.06136(10) 0.6186(3) 0.0274(6) Uani 1 1 d . . . . .
O6 O 1.1704(2) 0.10284(10) 0.4709(3) 0.0263(6) Uani 1 1 d . . . . .
O7 O 1.3713(4) 0.2843(2) 0.3394(9) 0.120(2) Uani 1 1 d . . . . .
H7 H 1.392963 0.255413 0.345493 0.180 Uiso 1 1 calc R U . . .
O8 O 0.4621(4) 0.20773(17) 0.5208(7) 0.0940(14) Uani 1 1 d . . . . .
H8A H 0.406465 0.210253 0.580982 0.141 Uiso 1 1 calc R U . . .
C1 C 0.6790(3) 0.37440(14) 0.5011(4) 0.0217(8) Uani 1 1 d . . . . .
C2 C 0.6230(3) 0.32974(15) 0.4684(5) 0.0302(9) Uani 1 1 d . . . . .
H2 H 0.545921 0.329605 0.448394 0.036 Uiso 1 1 calc R U . . .
C3 C 0.6816(3) 0.28581(15) 0.4658(5) 0.0282(9) Uani 1 1 d . . . . .
H3 H 0.643384 0.256135 0.444982 0.034 Uiso 1 1 calc R U . . .
C4 C 0.7972(3) 0.28490(14) 0.4938(4) 0.0229(8) Uani 1 1 d . . . . .
C5 C 0.8522(3) 0.32952(15) 0.5289(5) 0.0258(9) Uani 1 1 d . . . . .
H5 H 0.929102 0.329533 0.551014 0.031 Uiso 1 1 calc R U . . .
C6 C 0.7939(3) 0.37414(15) 0.5317(5) 0.0255(9) Uani 1 1 d . . . . .
H6 H 0.831944 0.403810 0.554025 0.031 Uiso 1 1 calc R U . . .
C7 C 0.8603(3) 0.23751(14) 0.4863(4) 0.0226(8) Uani 1 1 d . . . . .
C8 C 0.8119(3) 0.19270(14) 0.5385(5) 0.0273(9) Uani 1 1 d . . . . .
H8 H 0.738936 0.192653 0.576472 0.033 Uiso 1 1 calc R U . . .
C9 C 0.8703(3) 0.14867(15) 0.5348(5) 0.0258(9) Uani 1 1 d . . . . .
H9 H 0.836686 0.119271 0.570307 0.031 Uiso 1 1 calc R U . . .
C10 C 0.9793(3) 0.14799(14) 0.4780(4) 0.0213(8) Uani 1 1 d . . . . .
C11 C 1.0283(3) 0.19209(15) 0.4255(5) 0.0273(9) Uani 1 1 d . . . . .
H11 H 1.101314 0.191950 0.387552 0.033 Uiso 1 1 calc R U . . .
C12 C 0.9696(3) 0.23621(14) 0.4291(5) 0.0252(9) Uani 1 1 d . . . . .
H12 H 1.003422 0.265494 0.392842 0.030 Uiso 1 1 calc R U . . .
C13 C 1.2550(6) 0.2854(3) 0.3432(14) 0.128(3) Uani 1 1 d . . . . .
H13A H 1.226877 0.312829 0.271838 0.192 Uiso 1 1 calc R U . . .
H13B H 1.233156 0.289223 0.465781 0.192 Uiso 1 1 calc R U . . .
H13C H 1.225048 0.254858 0.294519 0.192 Uiso 1 1 calc R U . . .
C14 C 0.4756(7) 0.1566(3) 0.4665(9) 0.107(3) Uani 1 1 d . . . . .
H14A H 0.499050 0.155502 0.344075 0.161 Uiso 1 1 calc R U . . .
H14B H 0.405864 0.139414 0.474588 0.161 Uiso 1 1 calc R U . . .
H14C H 0.530997 0.140953 0.544833 0.161 Uiso 1 1 calc R U . . .
C15 C 1.2396(3) 0.41362(14) 0.4744(5) 0.0258(9) Uani 1 1 d . . . . .
C16 C 0.7373(3) 0.02186(13) 0.5160(5) 0.0220(8) Uani 1 1 d . . . . .
N1 N 1.1288(3) 0.41224(14) 0.4656(4) 0.0378(9) Uani 1 1 d . . . . .
H1A H 1.092534 0.410670 0.563352 0.045 Uiso 1 1 calc R U . . .
H1B H 1.093255 0.412905 0.362202 0.045 Uiso 1 1 calc R U . . .
N2 N 1.2950(3) 0.41484(12) 0.3238(4) 0.0273(8) Uani 1 1 d . . . . .
H2A H 1.366794 0.414967 0.329092 0.033 Uiso 1 1 calc R U . . .
H2B H 1.259320 0.415510 0.220565 0.033 Uiso 1 1 calc R U . . .
N3 N 1.2938(3) 0.41259(12) 0.6330(4) 0.0273(8) Uani 1 1 d . . . . .
H3A H 1.365595 0.412715 0.638832 0.033 Uiso 1 1 calc R U . . .
H3B H 1.257417 0.411802 0.730735 0.033 Uiso 1 1 calc R U . . .
N4 N 0.6263(3) 0.02377(14) 0.5087(4) 0.0347(9) Uani 1 1 d . . . . .
H4A H 0.590501 0.024029 0.607081 0.042 Uiso 1 1 calc R U . . .
H4B H 0.590363 0.024752 0.405723 0.042 Uiso 1 1 calc R U . . .
N5 N 0.7910(3) 0.02121(11) 0.3641(4) 0.0255(7) Uani 1 1 d . . . . .
H5A H 0.862759 0.019796 0.367469 0.031 Uiso 1 1 calc R U . . .
H5B H 0.754406 0.022200 0.261739 0.031 Uiso 1 1 calc R U . . .
N6 N 0.7930(3) 0.02035(11) 0.6731(4) 0.0263(8) Uani 1 1 d . . . . .
H6A H 0.864679 0.018936 0.676999 0.032 Uiso 1 1 calc R U . . .
H6B H 0.757607 0.020783 0.771907 0.032 Uiso 1 1 calc R U . . .


_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 O1 1.458(3) . ?
S1 O2 1.458(2) . ?
S1 O3 1.458(3) . ?
S1 C1 1.769(4) . ?
S2 O4 1.460(3) . ?
S2 O5 1.458(3) . ?
S2 O6 1.460(3) . ?
S2 C10 1.768(4) . ?
O7 H7 0.8200 . ?
O7 C13 1.396(8) . ?
O8 H8A 0.8200 . ?
O8 C14 1.442(8) . ?
C1 C2 1.392(5) . ?
C1 C6 1.388(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(5) . ?
C4 C5 1.388(5) . ?
C4 C7 1.484(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.399(5) . ?
C7 C12 1.394(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.376(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.390(5) . ?
C10 C11 1.386(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.380(5) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N1 1.328(5) . ?
C15 N2 1.321(4) . ?
C15 N3 1.318(5) . ?
C16 N4 1.331(5) . ?
C16 N5 1.318(4) . ?
C16 N6 1.317(5) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?

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 S1 O3 112.54(15) . . ?
O1 S1 C1 106.13(17) . . ?
O2 S1 O1 112.08(15) . . ?
O2 S1 O3 112.41(15) . . ?
O2 S1 C1 107.07(16) . . ?
O3 S1 C1 106.05(16) . . ?
O4 S2 O6 112.53(14) . . ?
O4 S2 C10 106.42(16) . . ?
O5 S2 O4 111.82(16) . . ?
O5 S2 O6 112.72(15) . . ?
O5 S2 C10 106.18(15) . . ?
O6 S2 C10 106.61(17) . . ?
C13 O7 H7 109.5 . . ?
C14 O8 H8A 109.5 . . ?
C2 C1 S1 119.3(3) . . ?
C6 C1 S1 121.2(3) . . ?
C6 C1 C2 119.5(4) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.3(4) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C7 121.0(3) . . ?
C5 C4 C3 118.3(4) . . ?
C5 C4 C7 120.7(3) . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.0(4) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 119.9(4) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C4 120.8(3) . . ?
C12 C7 C4 121.3(3) . . ?
C12 C7 C8 117.9(3) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.2(3) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.2(4) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 S2 119.9(3) . . ?
C11 C10 S2 120.8(3) . . ?
C11 C10 C9 119.3(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 120.9(4) . . ?
C11 C12 H12 119.5 . . ?
O7 C13 H13A 109.5 . . ?
O7 C13 H13B 109.5 . . ?
O7 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O8 C14 H14A 109.5 . . ?
O8 C14 H14B 109.5 . . ?
O8 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 N1 119.8(3) . . ?
N3 C15 N1 119.9(3) . . ?
N3 C15 N2 120.3(3) . . ?
N5 C16 N4 119.3(3) . . ?
N6 C16 N4 120.4(3) . . ?
N6 C16 N5 120.3(3) . . ?
C15 N1 H1A 120.0 . . ?
C15 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C15 N2 H2A 120.0 . . ?
C15 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C15 N3 H3A 120.0 . . ?
C15 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C16 N4 H4A 120.0 . . ?
C16 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C16 N5 H5A 120.0 . . ?
C16 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C16 N6 H6A 120.0 . . ?
C16 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?

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 C1 C2 C3 179.9(3) . . . . ?
S1 C1 C6 C5 180.0(3) . . . . ?
S2 C10 C11 C12 177.1(3) . . . . ?
O1 S1 C1 C2 -171.1(3) . . . . ?
O1 S1 C1 C6 9.1(3) . . . . ?
O2 S1 C1 C2 69.0(3) . . . . ?
O2 S1 C1 C6 -110.8(3) . . . . ?
O3 S1 C1 C2 -51.2(3) . . . . ?
O3 S1 C1 C6 129.0(3) . . . . ?
O4 S2 C10 C9 81.1(3) . . . . ?
O4 S2 C10 C11 -96.0(3) . . . . ?
O5 S2 C10 C9 -38.2(3) . . . . ?
O5 S2 C10 C11 144.7(3) . . . . ?
O6 S2 C10 C9 -158.6(3) . . . . ?
O6 S2 C10 C11 24.3(3) . . . . ?
C1 C2 C3 C4 -0.6(6) . . . . ?
C2 C1 C6 C5 0.2(5) . . . . ?
C2 C3 C4 C5 1.5(5) . . . . ?
C2 C3 C4 C7 -178.5(3) . . . . ?
C3 C4 C5 C6 -1.6(5) . . . . ?
C3 C4 C7 C8 -31.4(5) . . . . ?
C3 C4 C7 C12 149.3(4) . . . . ?
C4 C5 C6 C1 0.8(5) . . . . ?
C4 C7 C8 C9 -179.0(3) . . . . ?
C4 C7 C12 C11 178.9(3) . . . . ?
C5 C4 C7 C8 148.6(4) . . . . ?
C5 C4 C7 C12 -30.7(5) . . . . ?
C6 C1 C2 C3 -0.3(5) . . . . ?
C7 C4 C5 C6 178.4(3) . . . . ?
C7 C8 C9 C10 -0.2(6) . . . . ?
C8 C7 C12 C11 -0.5(5) . . . . ?
C8 C9 C10 S2 -177.2(3) . . . . ?
C8 C9 C10 C11 0.0(5) . . . . ?
C9 C10 C11 C12 -0.1(5) . . . . ?
C10 C11 C12 C7 0.3(6) . . . . ?
C12 C7 C8 C9 0.4(5) . . . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.084
_oxdiff_exptl_absorpt_empirical_full_min 0.881
####################################################################### 
# 
# 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_12345
_database_code_depnum_ccdc_archive 'CCDC 2152721'
loop_
_audit_author_name
_audit_author_address
'Shuqin Qin'
;Jinan University
China
;
_audit_update_record             
;
2022-02-17 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_audit_creation_date             2021-12-13
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 O6 S2, C11 H14 O2, 2(C H6 N3)'
_chemical_formula_sum            'C25 H34 N6 O8 S2'
_chemical_formula_weight         610.70
_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 0.0181 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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1959(3)
_cell_length_b                   7.1931(3)
_cell_length_c                   14.6132(6)
_cell_angle_alpha                101.192(4)
_cell_angle_beta                 90.032(4)
_cell_angle_gamma                93.056(4)
_cell_volume                     637.94(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4375
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.6390
_cell_measurement_theta_min      6.1570
_shelx_estimated_absorpt_T_max   0.791
_shelx_estimated_absorpt_T_min   0.757
_exptl_absorpt_coefficient_mu    2.458
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             322
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5959
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.737
_diffrn_reflns_theta_min         3.083
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       multi-scan
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5306
_reflns_number_total             5959
_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 > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         1.393
_refine_diff_density_min         -0.981
_refine_diff_density_rms         0.153
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.331
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5959
_refine_ls_number_restraints     278
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0959
_refine_ls_restrained_S_all      1.400
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2744
_refine_ls_wR_factor_ref         0.2836
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.403(3)
 0.597(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C2-O4
 1.38 with sigma of 0.02
 C4-C7
 1.5 with sigma of 0.02
 O5-C1
 1.38 with sigma of 0.02
 O4-C11
 1.4 with sigma of 0.02
 C6-O5
 2.3 with sigma of 0.02
 O4-C3
 2.3 with sigma of 0.02
 O5-C10
 1.4 with sigma of 0.02
 C8-C9
 1.55 with sigma of 0.02
 C7-C9
 2.5 with sigma of 0.02
 C7-C8
 1.37 with sigma of 0.02
 C11-C3
 2.4 with sigma of 0.02
 C6B-C1A \\sim C6B-C5B \\sim C5B-C4A \\sim C3B-C4A \\sim C3B-C2B \\sim C2B-C1A
 with sigma of 0.02
 C2A-C1A \\sim C2A-C3A \\sim C3A-C4A \\sim C5A-C4A \\sim C6A-C5A \\sim C6A-C1A
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C3) \\sim Ueq, Uanis(O4) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C11) \\sim
Ueq, Uanis(C1) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(O5)
\\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C10) \\sim Ueq,
Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C1A, C2B, C3B, C4A, C5B, C6B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C1A, C2A, C3A, C4A, C5A, C6A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O4, O5, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Sof(C2B)=Sof(H2B)=Sof(C3B)=Sof(H3B)=Sof(C5B)=Sof(H5B)=Sof(C6B)=Sof(H6B)=1-
 FVAR(1)
 Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=FVAR(1)
 Fixed Sof: O4(0.5) O5(0.5) C3(0.5) H3(0.5) C4(0.5) C5(0.5) H5(0.5) C6(0.5)
 H6(0.5) C1(0.5) C2(0.5) C7(0.5) H7(0.5) C8(0.5) H8(0.5) C9(0.5) H9A(0.5)
 H9B(0.5) H9C(0.5) C10(0.5) H10A(0.5) H10B(0.5) H10C(0.5) C11(0.5) H11A(0.5)
 H11B(0.5) H11C(0.5)
7.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C2A(H2A), C2B(H2B), C3A(H3A),
 C3B(H3B), C5A(H5A), C5B(H5B), C6A(H6A), C6B(H6B)
7.b Fitted hexagon refined as free rotating group:
 C3(C4,C5,C6,C1,C2)
7.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2C,H2D), N3(H3C,H3D)
7.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_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 0.66055(11) 1.28104(10) 0.13979(5) 0.0204(4) Uani 1 1 d . . . . .
O1 O 0.8951(4) 1.2954(3) 0.13072(17) 0.0246(6) Uani 1 1 d . . . . .
O2 O 0.5747(4) 1.0852(3) 0.11618(18) 0.0265(6) Uani 1 1 d . . . . .
O3 O 0.5515(4) 1.4058(4) 0.08947(18) 0.0291(7) Uani 1 1 d . . . . .
O4 O 0.184(4) 0.913(5) 0.3569(15) 0.204(8) Uani 0.5 1 d D U P A -1
O5 O 0.485(3) 1.0650(18) 0.5984(11) 0.123(4) Uani 0.5 1 d D U P A -1
C3 C -0.063(3) 0.984(2) 0.4562(10) 0.125(4) Uani 0.5 1 d DG U P A -1
H3 H -0.136688 0.953125 0.397643 0.150 Uiso 0.5 1 calc R U P A -1
C4 C -0.1806(19) 1.028(3) 0.5380(14) 0.189(8) Uani 0.5 1 d DG U P A -1
C5 C -0.073(3) 1.073(3) 0.6236(11) 0.139(5) Uani 0.5 1 d G U P A -1
H5 H -0.153514 1.102681 0.679513 0.167 Uiso 0.5 1 calc R U P A -1
C6 C 0.151(3) 1.075(3) 0.6275(10) 0.177(7) Uani 0.5 1 d DG U P A -1
H6 H 0.224079 1.106321 0.686095 0.213 Uiso 0.5 1 calc R U P A -1
C1 C 0.268(2) 1.032(3) 0.5458(13) 0.133(5) Uani 0.5 1 d DG U P A -1
C2 C 0.161(3) 0.986(2) 0.4601(10) 0.169(7) Uani 0.5 1 d DG U P A -1
C7 C -0.417(5) 0.965(6) 0.518(3) 0.200(10) Uani 0.5 1 d D U P A -1
H7 H -0.444646 0.906868 0.570441 0.240 Uiso 0.5 1 calc R U P A -1
C8 C -0.615(6) 0.935(6) 0.478(3) 0.204(12) Uani 0.5 1 d D U P A -1
H8 H -0.734281 0.940325 0.519042 0.245 Uiso 0.5 1 calc R U P A -1
C9 C -0.669(5) 0.893(5) 0.376(2) 0.171(11) Uani 0.5 1 d D U P A -1
H9A H -0.820180 0.846549 0.366673 0.257 Uiso 0.5 1 calc R U P A -1
H9B H -0.575024 0.796753 0.343583 0.257 Uiso 0.5 1 calc R U P A -1
H9C H -0.646293 1.009701 0.350942 0.257 Uiso 0.5 1 calc R U P A -1
C10 C 0.577(2) 1.128(3) 0.6924(12) 0.091(4) Uani 0.5 1 d D U P A -1
H10A H 0.462011 1.172504 0.735869 0.137 Uiso 0.5 1 calc R U P A -1
H10B H 0.685747 1.232406 0.692083 0.137 Uiso 0.5 1 calc R U P A -1
H10C H 0.645272 1.022416 0.712091 0.137 Uiso 0.5 1 calc R U P A -1
C11 C -0.019(5) 0.880(4) 0.2990(16) 0.157(9) Uani 0.5 1 d D U P A -1
H11A H -0.086101 1.000865 0.301204 0.235 Uiso 0.5 1 calc R U P A -1
H11B H -0.119268 0.792168 0.323616 0.235 Uiso 0.5 1 calc R U P A -1
H11C H 0.016150 0.825072 0.234361 0.235 Uiso 0.5 1 calc R U P A -1
C12 C 1.0373(6) 1.7766(5) 0.0939(3) 0.0253(8) Uani 1 1 d . . . . .
C1A C 0.6074(5) 1.3586(5) 0.2597(2) 0.0256(8) Uani 1 1 d D . . . .
C2A C 0.4064(14) 1.423(2) 0.2830(6) 0.034(3) Uani 0.48(2) 1 d D . P B 1
H2A H 0.299779 1.429614 0.237161 0.041 Uiso 0.48(2) 1 calc R U P B 1
C2B C 0.4007(13) 1.326(3) 0.2966(6) 0.039(3) Uani 0.52(2) 1 d D . P B 2
H2B H 0.288917 1.262131 0.255967 0.047 Uiso 0.52(2) 1 calc R U P B 2
C3A C 0.3683(16) 1.479(2) 0.3783(6) 0.035(3) Uani 0.48(2) 1 d D . P B 1
H3A H 0.230720 1.524058 0.396756 0.042 Uiso 0.48(2) 1 calc R U P B 1
C3B C 0.3571(14) 1.385(3) 0.3907(7) 0.042(3) Uani 0.52(2) 1 d D . P B 2
H3B H 0.216279 1.366169 0.414110 0.051 Uiso 0.52(2) 1 calc R U P B 2
C4A C 0.5221(6) 1.4711(6) 0.4492(3) 0.0337(9) Uani 1 1 d D . . . .
C5A C 0.7229(16) 1.406(3) 0.4149(7) 0.048(4) Uani 0.48(2) 1 d D . P B 1
H5A H 0.834571 1.399611 0.458576 0.057 Uiso 0.48(2) 1 calc R U P B 1
C5B C 0.7232(15) 1.507(2) 0.4193(7) 0.039(3) Uani 0.52(2) 1 d D . P B 2
H5B H 0.832872 1.569481 0.461458 0.046 Uiso 0.52(2) 1 calc R U P B 2
C6A C 0.7662(17) 1.350(3) 0.3199(6) 0.045(4) Uani 0.48(2) 1 d D . P B 1
H6A H 0.903590 1.307274 0.299130 0.054 Uiso 0.48(2) 1 calc R U P B 1
C6B C 0.7654(15) 1.449(2) 0.3239(6) 0.034(2) Uani 0.52(2) 1 d D . P B 2
H6B H 0.906923 1.471620 0.302076 0.041 Uiso 0.52(2) 1 calc R U P B 2
N1 N 1.1525(5) 1.6257(4) 0.0941(2) 0.0320(8) Uani 1 1 d . . . . .
H1A H 1.086649 1.514511 0.094706 0.038 Uiso 1 1 calc R U . . .
H1B H 1.294623 1.637159 0.093632 0.038 Uiso 1 1 calc R U . . .
N2 N 0.8243(5) 1.7576(4) 0.0946(3) 0.0346(8) Uani 1 1 d . . . . .
H2C H 0.746991 1.856947 0.095138 0.042 Uiso 1 1 calc R U . . .
H2D H 0.759635 1.645646 0.094460 0.042 Uiso 1 1 calc R U . . .
N3 N 1.1332(5) 1.9459(4) 0.0940(2) 0.0285(7) Uani 1 1 d . . . . .
H3C H 1.054836 2.044669 0.094608 0.034 Uiso 1 1 calc R U . . .
H3D H 1.275133 1.959599 0.093571 0.034 Uiso 1 1 calc R U . . .


_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 O1 1.459(2) . ?
S1 O2 1.455(2) . ?
S1 O3 1.457(2) . ?
S1 C1A 1.770(3) . ?
O4 C2 1.51(2) . ?
O4 C11 1.49(2) . ?
O5 C1 1.535(17) . ?
O5 C10 1.465(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.3900 . ?
C3 C2 1.3900 . ?
C4 C5 1.3900 . ?
C4 C7 1.52(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.3900 . ?
C6 H6 0.9500 . ?
C6 C1 1.3900 . ?
C1 C2 1.3900 . ?
C7 H7 0.9500 . ?
C7 C8 1.35(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.49(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N1 1.331(5) . ?
C12 N2 1.319(4) . ?
C12 N3 1.326(5) . ?
C1A C2A 1.372(8) . ?
C1A C2B 1.416(8) . ?
C1A C6A 1.331(10) . ?
C1A C6B 1.397(9) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.395(11) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.390(11) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.418(9) . ?
C3B H3B 0.9500 . ?
C3B C4A 1.373(9) . ?
C4A C4A 1.491(7) 2_686 ?
C4A C5A 1.411(10) . ?
C4A C5B 1.349(9) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.398(12) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.405(11) . ?
C6A H6A 0.9500 . ?
C6B H6B 0.9500 . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 H2C 0.8800 . ?
N2 H2D 0.8800 . ?
N3 H3C 0.8800 . ?
N3 H3D 0.8800 . ?

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 S1 C1A 106.11(15) . . ?
O2 S1 O1 111.83(14) . . ?
O2 S1 O3 112.69(15) . . ?
O2 S1 C1A 105.94(16) . . ?
O3 S1 O1 112.66(15) . . ?
O3 S1 C1A 107.02(16) . . ?
C11 O4 C2 117.3(18) . . ?
C10 O5 C1 141.4(15) . . ?
C4 C3 H3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 C7 110(2) . . ?
C5 C4 C7 128(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C1 120.0 . . ?
C1 C6 H6 120.0 . . ?
C6 C1 O5 92.7(12) . . ?
C2 C1 O5 147.3(12) . . ?
C2 C1 C6 120.0 . . ?
C3 C2 O4 94.2(13) . . ?
C1 C2 O4 145.5(13) . . ?
C1 C2 C3 120.0 . . ?
C4 C7 H7 98.8 . . ?
C8 C7 C4 162(4) . . ?
C8 C7 H7 98.8 . . ?
C7 C8 H8 116.2 . . ?
C7 C8 C9 128(3) . . ?
C9 C8 H8 116.2 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O5 C10 H10A 109.5 . . ?
O5 C10 H10B 109.5 . . ?
O5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 N1 119.4(3) . . ?
N2 C12 N3 119.5(3) . . ?
N3 C12 N1 121.0(3) . . ?
C2A C1A S1 117.4(4) . . ?
C2B C1A S1 121.0(4) . . ?
C6A C1A S1 117.2(5) . . ?
C6A C1A C2A 125.4(7) . . ?
C6B C1A S1 122.9(5) . . ?
C6B C1A C2B 116.1(6) . . ?
C1A C2A H2A 122.1 . . ?
C1A C2A C3A 115.8(7) . . ?
C3A C2A H2A 122.1 . . ?
C1A C2B H2B 119.2 . . ?
C3B C2B C1A 121.6(7) . . ?
C3B C2B H2B 119.2 . . ?
C2A C3A H3A 117.9 . . ?
C2A C3A C4A 124.1(7) . . ?
C4A C3A H3A 117.9 . . ?
C2B C3B H3B 120.7 . . ?
C4A C3B C2B 118.6(7) . . ?
C4A C3B H3B 120.7 . . ?
C3A C4A C4A 123.4(5) . 2_686 ?
C3B C4A C4A 118.7(5) . 2_686 ?
C5A C4A C3A 113.7(6) . . ?
C5A C4A C4A 122.8(6) . 2_686 ?
C5B C4A C3B 123.2(7) . . ?
C5B C4A C4A 118.1(6) . 2_686 ?
C4A C5A H5A 118.3 . . ?
C6A C5A C4A 123.5(8) . . ?
C6A C5A H5A 118.3 . . ?
C4A C5B H5B 121.1 . . ?
C4A C5B C6B 117.9(8) . . ?
C6B C5B H5B 121.1 . . ?
C1A C6A C5A 117.4(8) . . ?
C1A C6A H6A 121.3 . . ?
C5A C6A H6A 121.3 . . ?
C1A C6B C5B 122.6(8) . . ?
C1A C6B H6B 118.7 . . ?
C5B C6B H6B 118.7 . . ?
C12 N1 H1A 120.0 . . ?
C12 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C12 N2 H2C 120.0 . . ?
C12 N2 H2D 120.0 . . ?
H2C N2 H2D 120.0 . . ?
C12 N3 H3C 120.0 . . ?
C12 N3 H3D 120.0 . . ?
H3C N3 H3D 120.0 . . ?

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 C1A C2A C3A 178.4(7) . . . . ?
S1 C1A C2B C3B 179.6(8) . . . . ?
S1 C1A C6A C5A -178.2(9) . . . . ?
S1 C1A C6B C5B -178.8(7) . . . . ?
O1 S1 C1A C2A 157.3(9) . . . . ?
O1 S1 C1A C2B -166.5(10) . . . . ?
O1 S1 C1A C6A -22.6(12) . . . . ?
O1 S1 C1A C6B 11.3(8) . . . . ?
O2 S1 C1A C2A -83.7(9) . . . . ?
O2 S1 C1A C2B -47.5(10) . . . . ?
O2 S1 C1A C6A 96.5(12) . . . . ?
O2 S1 C1A C6B 130.3(8) . . . . ?
O3 S1 C1A C2A 36.8(9) . . . . ?
O3 S1 C1A C2B 73.0(10) . . . . ?
O3 S1 C1A C6A -143.1(12) . . . . ?
O3 S1 C1A C6B -109.2(8) . . . . ?
O5 C1 C2 O4 12(4) . . . . ?
O5 C1 C2 C3 -177(2) . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C3 C4 C7 C8 -45(13) . . . . ?
C4 C3 C2 O4 175(2) . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C4 C7 C8 C9 35(15) . . . . ?
C5 C4 C7 C8 152(11) . . . . ?
C5 C6 C1 O5 178.6(13) . . . . ?
C5 C6 C1 C2 0.0 . . . . ?
C6 C1 C2 O4 -171(3) . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C2 C3 C4 C7 -165(2) . . . . ?
C7 C4 C5 C6 162(3) . . . . ?
C10 O5 C1 C6 -4(2) . . . . ?
C10 O5 C1 C2 173.6(16) . . . . ?
C11 O4 C2 C3 2(3) . . . . ?
C11 O4 C2 C1 174.5(17) . . . . ?
C1A C2A C3A C4A -0.1(15) . . . . ?
C1A C2B C3B C4A -2.3(16) . . . . ?
C2A C1A C6A C5A 2.0(17) . . . . ?
C2A C3A C4A C4A -179.3(9) . . . 2_686 ?
C2A C3A C4A C5A 1.4(15) . . . . ?
C2B C1A C6B C5B -0.9(13) . . . . ?
C2B C3B C4A C4A -178.0(8) . . . 2_686 ?
C2B C3B C4A C5B 2.2(15) . . . . ?
C3A C4A C5A C6A -1.2(17) . . . . ?
C3B C4A C5B C6B -1.5(14) . . . . ?
C4A C4A C5A C6A 179.5(10) 2_686 . . . ?
C4A C4A C5B C6B 178.7(8) 2_686 . . . ?
C4A C5A C6A C1A -0.4(19) . . . . ?
C4A C5B C6B C1A 0.8(15) . . . . ?
C6A C1A C2A C3A -1.7(15) . . . . ?
C6B C1A C2B C3B 1.6(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.403(3)
2 0.597(3)

####################################################################### 
# 
# 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_gb_h
_database_code_depnum_ccdc_archive 'CCDC 2152723'
loop_
_audit_author_name
_audit_author_address
'Shuqin Qin'
;Jinan University
China
;
_audit_update_record             
;
2022-02-17 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_audit_creation_date             2021-12-14
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 O6 S2, C8 H11 N, 2(C H6 N3), 2(H2 O)'
_chemical_formula_sum            'C22 H35 N7 O8 S2'
_chemical_formula_weight         589.69
_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 0.0181 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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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           9
_space_group_name_H-M_alt        'I 1 a 1'
_space_group_name_Hall           'I -2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   8.3016(2)
_cell_length_b                   11.7965(3)
_cell_length_c                   30.4956(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.177(2)
_cell_angle_gamma                90
_cell_volume                     2974.25(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4411
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.5090
_cell_measurement_theta_min      4.0020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            5609
_diffrn_reflns_point_group_measured_fraction_full 0.584
_diffrn_reflns_point_group_measured_fraction_max 0.560
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.947
_diffrn_reflns_theta_min         2.910
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  39.00   1.00    1.00    --  -41.11  19.00 120.00  108
  2  ω     20.00  65.00   1.00    1.00    --   41.11 -99.00  60.00   45
  3  ω     35.00 133.00   1.00    2.00    --  107.58 -45.00  60.00   98
  4  ω     41.00 109.00   1.00    2.00    --  107.58 -94.00  60.00   68
  5  ω     30.00 105.00   1.00    2.00    --  107.58 -94.00-120.00   75
  6  ω     30.00  92.00   1.00    1.00    --   41.11-125.00-150.00   62
  7  ω    123.00 149.00   1.00    2.00    --  107.58  45.00-180.00   26
  8  ω    123.00 177.00   1.00    2.00    --  107.58  61.00-150.00   54
  9  ω    144.00 169.00   1.00    2.00    --  107.58 125.00 -90.00   25
 10  ω     96.00 176.00   1.00    2.00    --  107.58 125.00 150.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0749775000
_diffrn_orient_matrix_UB_12      0.0317481000
_diffrn_orient_matrix_UB_13      0.0464422000
_diffrn_orient_matrix_UB_21      -0.0200843000
_diffrn_orient_matrix_UB_22      -0.1233888000
_diffrn_orient_matrix_UB_23      0.0151287000
_diffrn_orient_matrix_UB_31      0.1693538000
_diffrn_orient_matrix_UB_32      -0.0287265000
_diffrn_orient_matrix_UB_33      -0.0137125000
_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'
_reflns_Friedel_coverage         0.157
_reflns_Friedel_fraction_full    0.167
_reflns_Friedel_fraction_max     0.153
_reflns_number_gt                3288
_reflns_number_total             3382
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.28(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         3382
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0712P)²+0.8828P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1066
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.72(3)
 0.28(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
3.a Riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), N3(H3A,H3B), N4(H4A,H4B), N5(H5A,H5B), N6(H6A,H6B),
 N7(H7D,H7E), O1W(H1WA,H1WB)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16),
 C17(H17), C19(H19), C20(H20)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.62494(9) -0.34780(6) 0.08342(2) 0.02344(19) Uani 1 1 d . . . . .
S2 S 0.38107(8) -0.34660(6) 0.41737(2) 0.02192(18) Uani 1 1 d . . . . .
O1 O 0.7608(3) -0.4226(2) 0.07872(9) 0.0308(5) Uani 1 1 d . . . . .
O2 O 0.4814(3) -0.3779(3) 0.05472(9) 0.0340(6) Uani 1 1 d . . . . .
O3 O 0.6655(3) -0.2281(2) 0.07895(9) 0.0333(6) Uani 1 1 d . . . . .
O4 O 0.3501(3) -0.2262(2) 0.42343(9) 0.0330(6) Uani 1 1 d . . . . .
O5 O 0.2437(3) -0.4163(2) 0.42656(8) 0.0292(5) Uani 1 1 d . . . . .
O6 O 0.5312(3) -0.3848(2) 0.44117(8) 0.0300(5) Uani 1 1 d . . . . .
C1 C 0.5213(6) 0.0576(4) 0.2526(2) 0.0543(10) Uani 1 1 d . . . . .
C2 C 0.4957(9) 0.1239(7) 0.2156(2) 0.079(2) Uani 1 1 d . . . . .
C3 C 0.4261(9) 0.2282(7) 0.2196(4) 0.100(3) Uani 1 1 d . . . . .
H3 H 0.405224 0.274051 0.194100 0.120 Uiso 1 1 calc R U . . .
C4 C 0.3861(7) 0.2680(5) 0.2590(4) 0.089(3) Uani 1 1 d . . . . .
H4 H 0.339758 0.341314 0.260739 0.107 Uiso 1 1 calc R U . . .
C5 C 0.4129(7) 0.2010(7) 0.2975(3) 0.093(3) Uani 1 1 d . . . . .
H5 H 0.382890 0.227831 0.324958 0.112 Uiso 1 1 calc R U . . .
C6 C 0.4862(6) 0.0921(5) 0.2940(2) 0.0633(15) Uani 1 1 d . . . . .
C7 C 0.5371(15) 0.0812(12) 0.1722(3) 0.147(5) Uani 1 1 d . . . . .
H7A H 0.501658 0.136118 0.149217 0.221 Uiso 1 1 calc R U . . .
H7B H 0.482557 0.008545 0.165831 0.221 Uiso 1 1 calc R U . . .
H7C H 0.654386 0.070573 0.172883 0.221 Uiso 1 1 calc R U . . .
C8 C 0.5135(11) 0.0188(10) 0.3344(3) 0.116(3) Uani 1 1 d . . . . .
H8A H 0.462658 -0.055282 0.328569 0.174 Uiso 1 1 calc R U . . .
H8B H 0.465582 0.055328 0.359015 0.174 Uiso 1 1 calc R U . . .
H8C H 0.629845 0.008768 0.341925 0.174 Uiso 1 1 calc R U . . .
C9 C 0.5689(4) -0.3628(3) 0.13767(11) 0.0241(7) Uani 1 1 d . . . . .
C10 C 0.4747(5) -0.2782(3) 0.15415(11) 0.0349(7) Uani 1 1 d . . . . .
H10 H 0.439663 -0.215717 0.136066 0.042 Uiso 1 1 calc R U . . .
C11 C 0.4320(5) -0.2849(3) 0.19691(11) 0.0342(7) Uani 1 1 d . . . . .
H11 H 0.367978 -0.226806 0.208150 0.041 Uiso 1 1 calc R U . . .
C12 C 0.4827(4) -0.3772(3) 0.22372(11) 0.0272(7) Uani 1 1 d . . . . .
C13 C 0.5699(5) -0.4628(3) 0.20593(11) 0.0323(7) Uani 1 1 d . . . . .
H13 H 0.600044 -0.527520 0.223311 0.039 Uiso 1 1 calc R U . . .
C14 C 0.6146(4) -0.4563(3) 0.16300(11) 0.0312(7) Uani 1 1 d . . . . .
H14 H 0.675697 -0.515439 0.151347 0.037 Uiso 1 1 calc R U . . .
C15 C 0.4487(4) -0.3770(3) 0.27091(11) 0.0282(7) Uani 1 1 d . . . . .
C16 C 0.3254(4) -0.3109(3) 0.28608(11) 0.0307(7) Uani 1 1 d . . . . .
H16 H 0.254356 -0.270743 0.265423 0.037 Uiso 1 1 calc R U . . .
C17 C 0.3045(4) -0.3026(3) 0.33042(11) 0.0308(7) Uani 1 1 d . . . . .
H17 H 0.220218 -0.257030 0.340072 0.037 Uiso 1 1 calc R U . . .
C18 C 0.4080(4) -0.3618(3) 0.36083(11) 0.0243(7) Uani 1 1 d . . . . .
C19 C 0.5265(5) -0.4314(3) 0.34670(11) 0.0336(7) Uani 1 1 d . . . . .
H19 H 0.593741 -0.474365 0.367388 0.040 Uiso 1 1 calc R U . . .
C20 C 0.5468(5) -0.4384(3) 0.30224(12) 0.0348(7) Uani 1 1 d . . . . .
H20 H 0.629252 -0.486007 0.292757 0.042 Uiso 1 1 calc R U . . .
C21 C 0.6087(4) -0.7397(3) 0.55372(12) 0.0276(7) Uani 1 1 d . . . . .
C22 C 0.3972(4) -0.7425(3) -0.05332(12) 0.0282(7) Uani 1 1 d . . . . .
N1 N 0.4032(4) -0.8504(3) -0.06438(14) 0.0343(7) Uani 1 1 d . . . . .
H1A H 0.316764 -0.890933 -0.066095 0.041 Uiso 1 1 d R U . . .
H1B H 0.493764 -0.880213 -0.069855 0.041 Uiso 1 1 d R U . . .
N2 N 0.5294(4) -0.6792(3) -0.05190(12) 0.0347(7) Uani 1 1 d . . . . .
H2A H 0.523837 -0.608523 -0.045384 0.042 Uiso 1 1 d R U . . .
H2B H 0.620347 -0.708483 -0.057374 0.042 Uiso 1 1 d R U . . .
N3 N 0.2586(4) -0.6954(3) -0.04420(13) 0.0386(8) Uani 1 1 d . . . . .
H3A H 0.171419 -0.735159 -0.045877 0.046 Uiso 1 1 d R U . . .
H3B H 0.255779 -0.624979 -0.036997 0.046 Uiso 1 1 d R U . . .
N4 N 0.7476(4) -0.6963(3) 0.54323(12) 0.0353(7) Uani 1 1 d . . . . .
H4A H 0.752111 -0.626158 0.535760 0.042 Uiso 1 1 d R U . . .
H4B H 0.832601 -0.738058 0.543710 0.042 Uiso 1 1 d R U . . .
N5 N 0.6004(5) -0.8490(3) 0.56547(13) 0.0339(7) Uani 1 1 d . . . . .
H5A H 0.510555 -0.876537 0.572644 0.041 Uiso 1 1 d R U . . .
H5B H 0.684895 -0.891247 0.566024 0.041 Uiso 1 1 d R U . . .
N6 N 0.4798(4) -0.6750(3) 0.55235(12) 0.0344(7) Uani 1 1 d . . . . .
H6A H 0.485390 -0.604936 0.544807 0.041 Uiso 1 1 d R U . . .
H6B H 0.389820 -0.702716 0.559307 0.041 Uiso 1 1 d R U . . .
N7 N 0.5845(6) -0.0508(4) 0.2484(3) 0.0912(19) Uani 1 1 d . . . . .
H7D H 0.611140 -0.090676 0.271475 0.109 Uiso 1 1 d R U . . .
H7E H 0.603380 -0.075716 0.222825 0.109 Uiso 1 1 d R U . . .
O1W O 0.4009(4) -0.4687(2) -0.02768(9) 0.0444(7) Uani 1 1 d . . . . .
H1WA H 0.414149 -0.539359 -0.023180 0.067 Uiso 1 1 d R U . . .
H1WB H 0.395469 -0.435019 -0.003230 0.067 Uiso 1 1 d R U . . .
O2W O 0.6022(4) -0.4647(3) 0.52699(10) 0.0438(8) Uani 1 1 d . . . . .
H2WA H 0.603(6) -0.409(5) 0.5415(16) 0.036(11) Uiso 1 1 d . . . . .
H2WB H 0.563(7) -0.449(5) 0.505(2) 0.065(18) Uiso 1 1 d . . . . .


_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 O1 1.449(3) . ?
S1 O2 1.458(3) . ?
S1 O3 1.461(3) . ?
S1 C9 1.767(3) . ?
S2 O4 1.459(3) . ?
S2 O5 1.454(3) . ?
S2 O6 1.456(3) . ?
S2 C18 1.767(3) . ?
C1 C2 1.374(9) . ?
C1 C6 1.384(9) . ?
C1 N7 1.391(6) . ?
C2 C3 1.369(12) . ?
C2 C7 1.485(12) . ?
C3 H3 0.9500 . ?
C3 C4 1.359(13) . ?
C4 H4 0.9500 . ?
C4 C5 1.415(12) . ?
C5 H5 0.9500 . ?
C5 C6 1.430(10) . ?
C6 C8 1.506(11) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.390(5) . ?
C9 C14 1.380(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.403(5) . ?
C12 C13 1.382(5) . ?
C12 C15 1.491(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.395(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.398(5) . ?
C15 C20 1.400(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.382(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.393(5) . ?
C18 C19 1.381(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.384(5) . ?
C20 H20 0.9500 . ?
C21 N4 1.326(5) . ?
C21 N5 1.341(5) . ?
C21 N6 1.312(5) . ?
C22 N1 1.319(5) . ?
C22 N2 1.325(5) . ?
C22 N3 1.330(5) . ?
N1 H1A 0.8598 . ?
N1 H1B 0.8599 . ?
N2 H2A 0.8598 . ?
N2 H2B 0.8599 . ?
N3 H3A 0.8599 . ?
N3 H3B 0.8600 . ?
N4 H4A 0.8603 . ?
N4 H4B 0.8597 . ?
N5 H5A 0.8598 . ?
N5 H5B 0.8597 . ?
N6 H6A 0.8603 . ?
N6 H6B 0.8595 . ?
N7 H7D 0.8597 . ?
N7 H7E 0.8601 . ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.8498 . ?
O2W H2WA 0.80(5) . ?
O2W H2WB 0.74(7) . ?

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 S1 O2 113.21(16) . . ?
O1 S1 O3 113.00(17) . . ?
O1 S1 C9 107.74(16) . . ?
O2 S1 O3 111.25(17) . . ?
O2 S1 C9 105.53(17) . . ?
O3 S1 C9 105.45(16) . . ?
O4 S2 C18 105.17(16) . . ?
O5 S2 O4 112.11(17) . . ?
O5 S2 O6 112.32(16) . . ?
O5 S2 C18 107.52(16) . . ?
O6 S2 O4 113.02(17) . . ?
O6 S2 C18 106.09(16) . . ?
C2 C1 C6 123.5(6) . . ?
C2 C1 N7 118.7(7) . . ?
C6 C1 N7 117.8(6) . . ?
C1 C2 C7 120.4(9) . . ?
C3 C2 C1 118.3(8) . . ?
C3 C2 C7 121.2(9) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.9(7) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.5(6) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.4(7) . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C5 117.3(6) . . ?
C1 C6 C8 123.4(7) . . ?
C5 C6 C8 119.3(7) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 S1 118.1(3) . . ?
C14 C9 S1 121.4(3) . . ?
C14 C9 C10 120.5(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C15 119.2(3) . . ?
C13 C12 C11 118.6(3) . . ?
C13 C12 C15 122.1(3) . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.4(3) . . ?
C14 C13 H13 119.3 . . ?
C9 C14 C13 119.1(3) . . ?
C9 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C16 C15 C12 121.9(3) . . ?
C16 C15 C20 117.4(3) . . ?
C20 C15 C12 120.6(3) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.6(3) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 120.3 . . ?
C16 C17 C18 119.4(3) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 S2 118.3(3) . . ?
C19 C18 S2 121.4(3) . . ?
C19 C18 C17 120.3(3) . . ?
C18 C19 H19 120.2 . . ?
C18 C19 C20 119.7(3) . . ?
C20 C19 H19 120.2 . . ?
C15 C20 H20 119.2 . . ?
C19 C20 C15 121.5(3) . . ?
C19 C20 H20 119.2 . . ?
N4 C21 N5 120.2(4) . . ?
N6 C21 N4 119.4(3) . . ?
N6 C21 N5 120.4(3) . . ?
N1 C22 N2 120.1(3) . . ?
N1 C22 N3 120.7(4) . . ?
N2 C22 N3 119.2(3) . . ?
C22 N1 H1A 120.1 . . ?
C22 N1 H1B 119.9 . . ?
H1A N1 H1B 120.0 . . ?
C22 N2 H2A 119.5 . . ?
C22 N2 H2B 120.5 . . ?
H2A N2 H2B 120.0 . . ?
C22 N3 H3A 119.9 . . ?
C22 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C21 N4 H4A 119.7 . . ?
C21 N4 H4B 120.3 . . ?
H4A N4 H4B 120.0 . . ?
C21 N5 H5A 119.9 . . ?
C21 N5 H5B 120.1 . . ?
H5A N5 H5B 120.0 . . ?
C21 N6 H6A 120.3 . . ?
C21 N6 H6B 119.7 . . ?
H6A N6 H6B 120.0 . . ?
C1 N7 H7D 119.9 . . ?
C1 N7 H7E 119.9 . . ?
H7D N7 H7E 120.0 . . ?
H1WA O1W H1WB 109.5 . . ?
H2WA O2W H2WB 106(6) . . ?

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 C9 C10 C11 -178.2(3) . . . . ?
S1 C9 C14 C13 178.7(3) . . . . ?
S2 C18 C19 C20 -178.1(3) . . . . ?
O1 S1 C9 C10 161.7(3) . . . . ?
O1 S1 C9 C14 -19.3(3) . . . . ?
O2 S1 C9 C10 -77.1(3) . . . . ?
O2 S1 C9 C14 102.0(3) . . . . ?
O3 S1 C9 C10 40.8(3) . . . . ?
O3 S1 C9 C14 -140.2(3) . . . . ?
O4 S2 C18 C17 -41.9(3) . . . . ?
O4 S2 C18 C19 139.0(3) . . . . ?
O5 S2 C18 C17 77.7(3) . . . . ?
O5 S2 C18 C19 -101.3(3) . . . . ?
O6 S2 C18 C17 -161.9(3) . . . . ?
O6 S2 C18 C19 19.0(3) . . . . ?
C1 C2 C3 C4 1.6(9) . . . . ?
C2 C1 C6 C5 2.8(8) . . . . ?
C2 C1 C6 C8 179.6(6) . . . . ?
C2 C3 C4 C5 -1.1(10) . . . . ?
C3 C4 C5 C6 1.4(8) . . . . ?
C4 C5 C6 C1 -2.2(8) . . . . ?
C4 C5 C6 C8 -179.1(5) . . . . ?
C6 C1 C2 C3 -2.5(9) . . . . ?
C6 C1 C2 C7 179.7(7) . . . . ?
C7 C2 C3 C4 179.3(7) . . . . ?
C9 C10 C11 C12 -0.3(6) . . . . ?
C10 C9 C14 C13 -2.3(5) . . . . ?
C10 C11 C12 C13 -2.7(6) . . . . ?
C10 C11 C12 C15 174.2(4) . . . . ?
C11 C12 C13 C14 3.3(5) . . . . ?
C11 C12 C15 C16 21.8(5) . . . . ?
C11 C12 C15 C20 -154.2(3) . . . . ?
C12 C13 C14 C9 -0.8(5) . . . . ?
C12 C15 C16 C17 -173.7(3) . . . . ?
C12 C15 C20 C19 174.1(4) . . . . ?
C13 C12 C15 C16 -161.4(3) . . . . ?
C13 C12 C15 C20 22.6(6) . . . . ?
C14 C9 C10 C11 2.8(6) . . . . ?
C15 C12 C13 C14 -173.5(3) . . . . ?
C15 C16 C17 C18 -0.3(5) . . . . ?
C16 C15 C20 C19 -2.1(6) . . . . ?
C16 C17 C18 S2 178.5(3) . . . . ?
C16 C17 C18 C19 -2.5(5) . . . . ?
C17 C18 C19 C20 2.9(6) . . . . ?
C18 C19 C20 C15 -0.6(6) . . . . ?
C20 C15 C16 C17 2.5(5) . . . . ?
N7 C1 C2 C3 176.8(5) . . . . ?
N7 C1 C2 C7 -0.9(9) . . . . ?
N7 C1 C6 C5 -176.6(5) . . . . ?
N7 C1 C6 C8 0.2(8) . . . . ?

_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 1.314
_oxdiff_exptl_absorpt_empirical_full_min 0.565
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.72(3)
2 0.28(3)

####################################################################### 
# 
# 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_exp_2670
_database_code_depnum_ccdc_archive 'CCDC 2152724'
loop_
_audit_author_name
_audit_author_address
'Shuqin Qin'
;Jinan University
China
;
_audit_update_record             
;
2022-02-17 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_audit_creation_date             2021-11-27
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C12 H8 O6 S2), C H6 N3, C12 H14 O3'
_chemical_formula_sum            'C19 H24 N3 O6 S'
_chemical_formula_weight         422.47
_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 0.0181 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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   12.5276(8)
_cell_length_b                   24.5907(16)
_cell_length_c                   28.4358(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8760.0(10)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    3997
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      72.9460
_cell_measurement_theta_min      3.8870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.651
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3568
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_unetI/netI     0.0760
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21675
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.073
_diffrn_reflns_theta_min         3.108
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  30.00   1.00    8.00    --  -40.73  57.00 120.00   27
  2  ω    -51.00 -24.00   1.00    8.00    --  -40.73  57.00 120.00   27
  3  ω     15.00  82.00   1.00    8.00    --   40.73 -99.00-120.00   67
  4  ω     47.00 108.00   1.00    8.00    --  107.58 -95.00-120.00   61
  5  ω     78.00 172.00   1.00    8.00    --  107.58  15.00 -90.00   94
  6  ω    108.00 168.00   1.00    8.00    --  107.58  45.00-180.00   60
  7  ω     25.00 100.00   1.00    8.00    --  107.58 -95.00  60.00   75
  8  ω   -113.00 -63.00   1.00    8.00    --  -40.73 -38.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1180460000
_diffrn_orient_matrix_UB_12      -0.0173809000
_diffrn_orient_matrix_UB_13      0.0013842000
_diffrn_orient_matrix_UB_21      0.0320092000
_diffrn_orient_matrix_UB_22      0.0579159000
_diffrn_orient_matrix_UB_23      0.0152685000
_diffrn_orient_matrix_UB_31      -0.0126767000
_diffrn_orient_matrix_UB_32      -0.0162952000
_diffrn_orient_matrix_UB_33      0.0519884000
_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'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5383
_reflns_number_total             8611
_reflns_odcompleteness_completeness 99.08
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     536
_refine_ls_number_reflns         8611
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0688
_refine_ls_restrained_S_all      1.055
_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)+(0.0707P)²+2.7977P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1618
_refine_ls_wR_factor_ref         0.1961
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C11A-H11C = C11A-H11D
 0.96 with sigma of 0.02
3.a Rotating group:
 N6(H6A,H6B)
3.b Secondary CH2 refined with riding coordinates:
 C9A(H9AA,H9AB), C9B(H9BA,H9BB)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C2A(H2A),
 C3A(H3A), C5A(H5A), C10A(H10A), C2B(H2B), C3B(H3B), C5B(H5B), C10B(H10B)
3.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2C,H2D), N3(H3C,H3D), N4(H4A,H4B), N5(H5C,H5D), C11B(H11A,
 H11B)
3.e Idealised Me refined as rotating group:
 C8A(H8AA,H8AB,H8AC), C12A(H12D,H12E,H12F), C8B(H8BA,H8BB,H8BC), C12B(H12A,
 H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.58500(7) 0.62058(3) 0.31931(3) 0.0411(2) Uani 1 1 d . . . . .
S2 S 0.73984(7) 0.62891(4) 0.68469(3) 0.0435(2) Uani 1 1 d . . . . .
O1 O 0.67153(18) 0.59126(10) 0.29607(8) 0.0456(6) Uani 1 1 d . . . . .
O2 O 0.48246(19) 0.59322(10) 0.31463(8) 0.0471(6) Uani 1 1 d . . . . .
O3 O 0.57796(19) 0.67739(10) 0.30504(8) 0.0474(6) Uani 1 1 d . . . . .
O4 O 0.6560(2) 0.66196(10) 0.70596(8) 0.0492(6) Uani 1 1 d . . . . .
O5 O 0.7348(2) 0.57233(10) 0.70035(9) 0.0508(6) Uani 1 1 d . . . . .
O6 O 0.84572(19) 0.65198(10) 0.69089(8) 0.0483(6) Uani 1 1 d . . . . .
C1 C 0.6148(3) 0.62104(13) 0.37971(12) 0.0404(8) Uani 1 1 d . . . . .
C2 C 0.5546(3) 0.65431(14) 0.40923(12) 0.0434(8) Uani 1 1 d . . . . .
H2 H 0.501510 0.676435 0.396741 0.052 Uiso 1 1 calc R U . . .
C3 C 0.5739(3) 0.65441(15) 0.45694(12) 0.0446(8) Uani 1 1 d . . . . .
H3 H 0.534523 0.677254 0.476388 0.054 Uiso 1 1 calc R U . . .
C4 C 0.6517(3) 0.62072(13) 0.47644(12) 0.0404(8) Uani 1 1 d . . . . .
C5 C 0.7101(3) 0.58722(14) 0.44644(12) 0.0423(8) Uani 1 1 d . . . . .
H5 H 0.762251 0.564514 0.458972 0.051 Uiso 1 1 calc R U . . .
C6 C 0.6924(3) 0.58701(14) 0.39861(13) 0.0445(8) Uani 1 1 d . . . . .
H6 H 0.731990 0.564298 0.379125 0.053 Uiso 1 1 calc R U . . .
C7 C 0.6727(3) 0.62172(13) 0.52777(12) 0.0392(7) Uani 1 1 d . . . . .
C8 C 0.5917(3) 0.63542(15) 0.55929(13) 0.0467(8) Uani 1 1 d . . . . .
H8 H 0.523317 0.642603 0.548159 0.056 Uiso 1 1 calc R U . . .
C9 C 0.6124(3) 0.63838(16) 0.60696(13) 0.0480(9) Uani 1 1 d . . . . .
H9 H 0.558172 0.648084 0.627632 0.058 Uiso 1 1 calc R U . . .
C10 C 0.7130(3) 0.62704(13) 0.62412(12) 0.0415(8) Uani 1 1 d . . . . .
C11 C 0.7941(3) 0.61214(14) 0.59310(13) 0.0445(8) Uani 1 1 d . . . . .
H11 H 0.861779 0.603736 0.604345 0.053 Uiso 1 1 calc R U . . .
C12 C 0.7728(3) 0.60999(14) 0.54569(12) 0.0425(8) Uani 1 1 d . . . . .
H12 H 0.827282 0.600384 0.525074 0.051 Uiso 1 1 calc R U . . .
C13 C 0.4573(3) 0.54597(15) 0.72184(12) 0.0454(8) Uani 1 1 d . . . . .
C14 C 0.3021(3) 0.70476(15) 0.27477(13) 0.0490(9) Uani 1 1 d . . . . .
N1 N 0.3189(3) 0.65337(13) 0.26240(11) 0.0589(9) Uani 1 1 d . . . . .
H1A H 0.375826 0.636880 0.271525 0.071 Uiso 1 1 calc R U . . .
H1B H 0.272953 0.636596 0.245258 0.071 Uiso 1 1 calc R U . . .
N2 N 0.2144(3) 0.73002(13) 0.26126(12) 0.0605(9) Uani 1 1 d . . . . .
H2C H 0.203357 0.763168 0.269591 0.073 Uiso 1 1 calc R U . . .
H2D H 0.168285 0.713345 0.244118 0.073 Uiso 1 1 calc R U . . .
N3 N 0.3728(3) 0.73028(13) 0.30102(11) 0.0573(9) Uani 1 1 d . . . . .
H3C H 0.361774 0.763422 0.309359 0.069 Uiso 1 1 calc R U . . .
H3D H 0.429946 0.713795 0.309813 0.069 Uiso 1 1 calc R U . . .
N4 N 0.5294(2) 0.52218(12) 0.69466(10) 0.0485(7) Uani 1 1 d . . . . .
H4A H 0.517639 0.490157 0.683649 0.058 Uiso 1 1 calc R U . . .
H4B H 0.587923 0.538753 0.688033 0.058 Uiso 1 1 calc R U . . .
N5 N 0.3675(2) 0.52060(13) 0.73202(10) 0.0499(8) Uani 1 1 d . . . . .
H5C H 0.355665 0.488578 0.721026 0.060 Uiso 1 1 calc R U . . .
H5D H 0.320702 0.536069 0.749663 0.060 Uiso 1 1 calc R U . . .
N6 N 0.4738(3) 0.59649(12) 0.73751(11) 0.0545(8) Uani 1 1 d . . . . .
H6A H 0.520915 0.611735 0.719925 0.065 Uiso 1 1 d R U . . .
H6B H 0.415084 0.614585 0.735991 0.065 Uiso 1 1 d R U . . .
O1A O 0.7744(2) 0.45664(10) 0.45799(9) 0.0527(6) Uani 1 1 d . . . . .
O2A O 0.7090(2) 0.37172(11) 0.46021(10) 0.0613(7) Uani 1 1 d . . . . .
O3A O 0.6294(2) 0.47135(12) 0.52584(9) 0.0583(7) Uani 1 1 d . . . . .
C1A C 0.8060(3) 0.45344(16) 0.50545(14) 0.0507(9) Uani 1 1 d . . . . .
C2A C 0.9106(3) 0.44509(19) 0.51591(16) 0.0649(11) Uani 1 1 d . . . . .
H2A H 0.959495 0.438620 0.491958 0.078 Uiso 1 1 calc R U . . .
C3A C 0.9444(4) 0.4462(2) 0.56259(17) 0.0761(14) Uani 1 1 d . . . . .
H3A H 1.016080 0.441057 0.569758 0.091 Uiso 1 1 calc R U . . .
C4A C 0.8712(4) 0.4550(2) 0.59829(16) 0.0683(12) Uani 1 1 d . . . . .
C5A C 0.7652(3) 0.46256(17) 0.58699(15) 0.0585(10) Uani 1 1 d . . . . .
H5A H 0.715679 0.467991 0.610913 0.070 Uiso 1 1 calc R U . . .
C6A C 0.7309(3) 0.46217(15) 0.54057(14) 0.0497(9) Uani 1 1 d . . . . .
C7A C 0.7226(3) 0.41328(16) 0.43939(14) 0.0500(9) Uani 1 1 d . . . . .
C8A C 0.6870(3) 0.42552(18) 0.39057(14) 0.0620(11) Uani 1 1 d . . . . .
H8AA H 0.631679 0.452524 0.391389 0.093 Uiso 1 1 calc R U . . .
H8AB H 0.660043 0.392967 0.376205 0.093 Uiso 1 1 calc R U . . .
H8AC H 0.746301 0.438967 0.372631 0.093 Uiso 1 1 calc R U . . .
C9A C 0.9051(4) 0.4543(3) 0.65017(17) 0.0916(17) Uani 1 1 d . . . . .
H9AA H 0.846127 0.467131 0.669270 0.110 Uiso 1 1 calc R U . . .
H9AB H 0.920120 0.417068 0.659345 0.110 Uiso 1 1 calc R U . . .
C10A C 0.9991(4) 0.4877(2) 0.65994(18) 0.0857(15) Uani 1 1 d . . . . .
H10A H 0.997669 0.523314 0.648834 0.103 Uiso 1 1 calc R U . . .
C11A C 1.0846(5) 0.4728(4) 0.6826(2) 0.100(2) Uani 1 1 d D . . . .
H11C H 1.083(6) 0.4336(11) 0.690(3) 0.16(3) Uiso 1 1 d D . . . .
H11D H 1.145(3) 0.495(2) 0.6922(18) 0.11(2) Uiso 1 1 d D . . . .
C12A C 0.5524(3) 0.48417(19) 0.56113(15) 0.0623(11) Uani 1 1 d . . . . .
H12D H 0.483843 0.489405 0.546700 0.093 Uiso 1 1 calc R U . . .
H12E H 0.573234 0.516885 0.577093 0.093 Uiso 1 1 calc R U . . .
H12F H 0.548187 0.454843 0.583339 0.093 Uiso 1 1 calc R U . . .
O1B O 1.0299(2) 0.71272(10) 0.59961(9) 0.0569(7) Uani 1 1 d . . . . .
O2B O 1.0594(2) 0.62245(11) 0.60201(9) 0.0523(6) Uani 1 1 d . . . . .
O3B O 0.8412(2) 0.75764(12) 0.59210(10) 0.0615(7) Uani 1 1 d . . . . .
C1B C 0.9816(3) 0.71125(15) 0.55528(14) 0.0500(9) Uani 1 1 d . . . . .
C2B C 1.0313(3) 0.69025(17) 0.51661(15) 0.0566(10) Uani 1 1 d . . . . .
H2B H 1.097026 0.673054 0.519601 0.068 Uiso 1 1 calc R U . . .
C3B C 0.9828(4) 0.69470(19) 0.47240(15) 0.0645(11) Uani 1 1 d . . . . .
H3B H 1.015880 0.679845 0.446106 0.077 Uiso 1 1 calc R U . . .
C4B C 0.8859(3) 0.72106(18) 0.46766(16) 0.0594(11) Uani 1 1 d . . . . .
C5B C 0.8373(3) 0.74235(17) 0.50696(16) 0.0598(11) Uani 1 1 d . . . . .
H5B H 0.772197 0.760136 0.503780 0.072 Uiso 1 1 calc R U . . .
C6B C 0.8834(3) 0.73789(15) 0.55153(15) 0.0516(9) Uani 1 1 d . . . . .
C7B C 1.0673(3) 0.66637(16) 0.61938(14) 0.0481(9) Uani 1 1 d . . . . .
C8B C 1.1173(3) 0.67898(18) 0.66563(14) 0.0616(11) Uani 1 1 d . . . . .
H8BA H 1.135700 0.645699 0.681300 0.092 Uiso 1 1 calc R U . . .
H8BB H 1.067835 0.699122 0.684638 0.092 Uiso 1 1 calc R U . . .
H8BC H 1.180599 0.700257 0.660755 0.092 Uiso 1 1 calc R U . . .
C9B C 0.8329(4) 0.7268(2) 0.41995(17) 0.0783(14) Uani 1 1 d . . . . .
H9BA H 0.810306 0.691032 0.409675 0.094 Uiso 1 1 calc R U . . .
H9BB H 0.769031 0.748733 0.423816 0.094 Uiso 1 1 calc R U . . .
C10B C 0.8939(5) 0.7498(4) 0.3845(2) 0.125(3) Uani 1 1 d . . . . .
H10B H 0.919770 0.784386 0.391209 0.150 Uiso 1 1 calc R U . . .
C11B C 0.9207(6) 0.7312(5) 0.3440(2) 0.184(5) Uani 1 1 d . . . . .
H11A H 0.898074 0.696845 0.334661 0.221 Uiso 1 1 calc R U . . .
H11B H 0.962822 0.752088 0.324032 0.221 Uiso 1 1 calc R U . . .
C12B C 0.7410(4) 0.7854(2) 0.5887(2) 0.0880(16) Uani 1 1 d . . . . .
H12A H 0.749558 0.817652 0.570088 0.132 Uiso 1 1 calc R U . . .
H12B H 0.717032 0.795212 0.619660 0.132 Uiso 1 1 calc R U . . .
H12C H 0.689366 0.761966 0.574227 0.132 Uiso 1 1 calc R U . . .


_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 O1 1.460(2) . ?
S1 O2 1.456(2) . ?
S1 O3 1.457(2) . ?
S1 C1 1.758(4) . ?
S2 O4 1.460(3) . ?
S2 O5 1.462(3) . ?
S2 O6 1.453(2) . ?
S2 C10 1.755(4) . ?
C1 C2 1.393(5) . ?
C1 C6 1.391(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.394(5) . ?
C4 C5 1.394(5) . ?
C4 C7 1.483(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.396(5) . ?
C7 C12 1.384(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.382(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.380(5) . ?
C10 C11 1.394(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.375(5) . ?
C12 H12 0.9300 . ?
C13 N4 1.325(4) . ?
C13 N5 1.319(4) . ?
C13 N6 1.336(4) . ?
C14 N1 1.329(5) . ?
C14 N2 1.319(5) . ?
C14 N3 1.317(5) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 H2C 0.8600 . ?
N2 H2D 0.8600 . ?
N3 H3C 0.8600 . ?
N3 H3D 0.8600 . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 H5C 0.8600 . ?
N5 H5D 0.8600 . ?
N6 H6A 0.8595 . ?
N6 H6B 0.8611 . ?
O1A C1A 1.409(4) . ?
O1A C7A 1.356(5) . ?
O2A C7A 1.193(5) . ?
O3A C6A 1.358(4) . ?
O3A C12A 1.427(4) . ?
C1A C2A 1.358(6) . ?
C1A C6A 1.389(5) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.393(6) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.385(6) . ?
C4A C5A 1.380(6) . ?
C4A C9A 1.535(6) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.388(5) . ?
C7A C8A 1.489(5) . ?
C8A H8AA 0.9600 . ?
C8A H8AB 0.9600 . ?
C8A H8AC 0.9600 . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C9A C10A 1.463(7) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.302(8) . ?
C11A H11C 0.99(2) . ?
C11A H11D 0.97(2) . ?
C12A H12D 0.9600 . ?
C12A H12E 0.9600 . ?
C12A H12F 0.9600 . ?
O1B C1B 1.399(4) . ?
O1B C7B 1.354(4) . ?
O2B C7B 1.192(4) . ?
O3B C6B 1.359(5) . ?
O3B C12B 1.432(5) . ?
C1B C2B 1.365(6) . ?
C1B C6B 1.398(5) . ?
C2B H2B 0.9300 . ?
C2B C3B 1.400(5) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.382(6) . ?
C4B C5B 1.376(6) . ?
C4B C9B 1.517(6) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.397(5) . ?
C7B C8B 1.489(5) . ?
C8B H8BA 0.9600 . ?
C8B H8BB 0.9600 . ?
C8B H8BC 0.9600 . ?
C9B H9BA 0.9700 . ?
C9B H9BB 0.9700 . ?
C9B C10B 1.384(7) . ?
C10B H10B 0.9300 . ?
C10B C11B 1.285(9) . ?
C11B H11A 0.9300 . ?
C11B H11B 0.9300 . ?
C12B H12A 0.9600 . ?
C12B H12B 0.9600 . ?
C12B H12C 0.9600 . ?

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 S1 C1 106.73(15) . . ?
O2 S1 O1 112.67(14) . . ?
O2 S1 O3 111.35(15) . . ?
O2 S1 C1 106.22(15) . . ?
O3 S1 O1 113.11(14) . . ?
O3 S1 C1 106.18(15) . . ?
O4 S2 O5 111.86(15) . . ?
O4 S2 C10 106.45(15) . . ?
O5 S2 C10 105.40(16) . . ?
O6 S2 O4 112.92(15) . . ?
O6 S2 O5 111.98(15) . . ?
O6 S2 C10 107.69(15) . . ?
C2 C1 S1 118.5(3) . . ?
C6 C1 S1 121.5(3) . . ?
C6 C1 C2 119.9(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.9(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C7 120.4(3) . . ?
C5 C4 C3 118.4(3) . . ?
C5 C4 C7 121.3(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 H6 120.3 . . ?
C8 C7 C4 120.5(3) . . ?
C12 C7 C4 121.3(3) . . ?
C12 C7 C8 118.2(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.5(3) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 S2 121.1(3) . . ?
C9 C10 C11 119.6(3) . . ?
C11 C10 S2 119.2(3) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.3(3) . . ?
C12 C11 H11 120.3 . . ?
C7 C12 H12 119.1 . . ?
C11 C12 C7 121.9(3) . . ?
C11 C12 H12 119.1 . . ?
N4 C13 N6 120.0(3) . . ?
N5 C13 N4 120.1(3) . . ?
N5 C13 N6 119.9(3) . . ?
N2 C14 N1 120.2(3) . . ?
N3 C14 N1 119.8(3) . . ?
N3 C14 N2 120.0(3) . . ?
C14 N1 H1A 120.0 . . ?
C14 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C14 N2 H2C 120.0 . . ?
C14 N2 H2D 120.0 . . ?
H2C N2 H2D 120.0 . . ?
C14 N3 H3C 120.0 . . ?
C14 N3 H3D 120.0 . . ?
H3C N3 H3D 120.0 . . ?
C13 N4 H4A 120.0 . . ?
C13 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C13 N5 H5C 120.0 . . ?
C13 N5 H5D 120.0 . . ?
H5C N5 H5D 120.0 . . ?
C13 N6 H6A 108.5 . . ?
C13 N6 H6B 109.3 . . ?
H6A N6 H6B 109.4 . . ?
C7A O1A C1A 117.7(3) . . ?
C6A O3A C12A 116.9(3) . . ?
C2A C1A O1A 119.3(4) . . ?
C2A C1A C6A 121.3(4) . . ?
C6A C1A O1A 119.3(4) . . ?
C1A C2A H2A 120.1 . . ?
C1A C2A C3A 119.9(4) . . ?
C3A C2A H2A 120.1 . . ?
C2A C3A H3A 120.0 . . ?
C4A C3A C2A 120.0(4) . . ?
C4A C3A H3A 120.0 . . ?
C3A C4A C9A 121.3(4) . . ?
C5A C4A C3A 119.2(4) . . ?
C5A C4A C9A 119.5(4) . . ?
C4A C5A H5A 119.4 . . ?
C4A C5A C6A 121.2(4) . . ?
C6A C5A H5A 119.4 . . ?
O3A C6A C1A 116.0(4) . . ?
O3A C6A C5A 125.5(4) . . ?
C5A C6A C1A 118.4(4) . . ?
O1A C7A C8A 110.4(3) . . ?
O2A C7A O1A 123.2(4) . . ?
O2A C7A C8A 126.4(4) . . ?
C7A C8A H8AA 109.5 . . ?
C7A C8A H8AB 109.5 . . ?
C7A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
C4A C9A H9AA 108.9 . . ?
C4A C9A H9AB 108.9 . . ?
H9AA C9A H9AB 107.7 . . ?
C10A C9A C4A 113.5(5) . . ?
C10A C9A H9AA 108.9 . . ?
C10A C9A H9AB 108.9 . . ?
C9A C10A H10A 116.7 . . ?
C11A C10A C9A 126.7(7) . . ?
C11A C10A H10A 116.7 . . ?
C10A C11A H11C 111(5) . . ?
C10A C11A H11D 128(4) . . ?
H11C C11A H11D 121(6) . . ?
O3A C12A H12D 109.5 . . ?
O3A C12A H12E 109.5 . . ?
O3A C12A H12F 109.5 . . ?
H12D C12A H12E 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
C7B O1B C1B 120.1(3) . . ?
C6B O3B C12B 117.1(3) . . ?
C2B C1B O1B 122.6(3) . . ?
C2B C1B C6B 121.1(4) . . ?
C6B C1B O1B 116.0(4) . . ?
C1B C2B H2B 120.1 . . ?
C1B C2B C3B 119.7(4) . . ?
C3B C2B H2B 120.1 . . ?
C2B C3B H3B 119.8 . . ?
C4B C3B C2B 120.3(4) . . ?
C4B C3B H3B 119.8 . . ?
C3B C4B C9B 121.0(4) . . ?
C5B C4B C3B 119.2(4) . . ?
C5B C4B C9B 119.8(4) . . ?
C4B C5B H5B 119.2 . . ?
C4B C5B C6B 121.6(4) . . ?
C6B C5B H5B 119.2 . . ?
O3B C6B C1B 116.4(3) . . ?
O3B C6B C5B 125.5(4) . . ?
C5B C6B C1B 118.0(4) . . ?
O1B C7B C8B 109.7(3) . . ?
O2B C7B O1B 124.2(4) . . ?
O2B C7B C8B 126.2(4) . . ?
C7B C8B H8BA 109.5 . . ?
C7B C8B H8BB 109.5 . . ?
C7B C8B H8BC 109.5 . . ?
H8BA C8B H8BB 109.5 . . ?
H8BA C8B H8BC 109.5 . . ?
H8BB C8B H8BC 109.5 . . ?
C4B C9B H9BA 108.2 . . ?
C4B C9B H9BB 108.2 . . ?
H9BA C9B H9BB 107.3 . . ?
C10B C9B C4B 116.5(4) . . ?
C10B C9B H9BA 108.2 . . ?
C10B C9B H9BB 108.2 . . ?
C9B C10B H10B 114.7 . . ?
C11B C10B C9B 130.7(9) . . ?
C11B C10B H10B 114.7 . . ?
C10B C11B H11A 120.0 . . ?
C10B C11B H11B 120.0 . . ?
H11A C11B H11B 120.0 . . ?
O3B C12B H12A 109.5 . . ?
O3B C12B H12B 109.5 . . ?
O3B C12B H12C 109.5 . . ?
H12A C12B H12B 109.5 . . ?
H12A C12B H12C 109.5 . . ?
H12B C12B H12C 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
S1 C1 C2 C3 178.1(3) . . . . ?
S1 C1 C6 C5 -177.5(3) . . . . ?
S2 C10 C11 C12 179.2(3) . . . . ?
O1 S1 C1 C2 169.2(3) . . . . ?
O1 S1 C1 C6 -14.3(3) . . . . ?
O2 S1 C1 C2 -70.3(3) . . . . ?
O2 S1 C1 C6 106.2(3) . . . . ?
O3 S1 C1 C2 48.3(3) . . . . ?
O3 S1 C1 C6 -135.2(3) . . . . ?
O4 S2 C10 C9 -20.4(3) . . . . ?
O4 S2 C10 C11 161.7(3) . . . . ?
O5 S2 C10 C9 98.6(3) . . . . ?
O5 S2 C10 C11 -79.4(3) . . . . ?
O6 S2 C10 C9 -141.7(3) . . . . ?
O6 S2 C10 C11 40.3(3) . . . . ?
C1 C2 C3 C4 -1.3(5) . . . . ?
C2 C1 C6 C5 -1.0(5) . . . . ?
C2 C3 C4 C5 0.5(5) . . . . ?
C2 C3 C4 C7 179.2(3) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C3 C4 C7 C8 28.6(5) . . . . ?
C3 C4 C7 C12 -150.4(3) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
C4 C7 C8 C9 -177.5(3) . . . . ?
C4 C7 C12 C11 178.3(3) . . . . ?
C5 C4 C7 C8 -152.7(3) . . . . ?
C5 C4 C7 C12 28.3(5) . . . . ?
C6 C1 C2 C3 1.6(5) . . . . ?
C7 C4 C5 C6 -178.6(3) . . . . ?
C7 C8 C9 C10 -1.0(6) . . . . ?
C8 C7 C12 C11 -0.8(5) . . . . ?
C8 C9 C10 S2 -178.3(3) . . . . ?
C8 C9 C10 C11 -0.4(5) . . . . ?
C9 C10 C11 C12 1.2(5) . . . . ?
C10 C11 C12 C7 -0.6(5) . . . . ?
C12 C7 C8 C9 1.6(5) . . . . ?
O1A C1A C2A C3A 174.8(4) . . . . ?
O1A C1A C6A O3A 2.4(5) . . . . ?
O1A C1A C6A C5A -175.6(3) . . . . ?
C1A O1A C7A O2A -5.1(5) . . . . ?
C1A O1A C7A C8A 175.1(3) . . . . ?
C1A C2A C3A C4A 1.0(8) . . . . ?
C2A C1A C6A O3A 178.5(4) . . . . ?
C2A C1A C6A C5A 0.4(6) . . . . ?
C2A C3A C4A C5A 0.1(8) . . . . ?
C2A C3A C4A C9A 177.5(5) . . . . ?
C3A C4A C5A C6A -0.9(7) . . . . ?
C3A C4A C9A C10A 49.2(7) . . . . ?
C4A C5A C6A O3A -177.2(4) . . . . ?
C4A C5A C6A C1A 0.6(6) . . . . ?
C4A C9A C10A C11A -129.5(6) . . . . ?
C5A C4A C9A C10A -133.3(5) . . . . ?
C6A C1A C2A C3A -1.2(7) . . . . ?
C7A O1A C1A C2A 105.0(4) . . . . ?
C7A O1A C1A C6A -78.8(4) . . . . ?
C9A C4A C5A C6A -178.4(4) . . . . ?
C12A O3A C6A C1A -175.7(3) . . . . ?
C12A O3A C6A C5A 2.1(6) . . . . ?
O1B C1B C2B C3B -173.9(3) . . . . ?
O1B C1B C6B O3B -6.1(5) . . . . ?
O1B C1B C6B C5B 173.6(3) . . . . ?
C1B O1B C7B O2B -2.4(6) . . . . ?
C1B O1B C7B C8B 178.5(3) . . . . ?
C1B C2B C3B C4B 1.1(6) . . . . ?
C2B C1B C6B O3B -179.5(3) . . . . ?
C2B C1B C6B C5B 0.1(5) . . . . ?
C2B C3B C4B C5B -0.7(6) . . . . ?
C2B C3B C4B C9B 179.3(4) . . . . ?
C3B C4B C5B C6B -0.1(6) . . . . ?
C3B C4B C9B C10B -53.8(8) . . . . ?
C4B C5B C6B O3B 180.0(4) . . . . ?
C4B C5B C6B C1B 0.4(6) . . . . ?
C4B C9B C10B C11B 122.4(8) . . . . ?
C5B C4B C9B C10B 126.2(6) . . . . ?
C6B C1B C2B C3B -0.9(6) . . . . ?
C7B O1B C1B C2B -55.6(5) . . . . ?
C7B O1B C1B C6B 131.1(4) . . . . ?
C9B C4B C5B C6B 180.0(4) . . . . ?
C12B O3B C6B C1B 179.5(4) . . . . ?
C12B O3B C6B C5B -0.1(6) . . . . ?

_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 1.878
_oxdiff_exptl_absorpt_empirical_full_min 0.542
####################################################################### 
# 
# 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_ysbhz_2
_database_code_depnum_ccdc_archive 'CCDC 2152725'
loop_
_audit_author_name
_audit_author_address
'Shuqin Qin'
;Jinan University
China
;
_audit_update_record             
;
2022-02-17 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_audit_creation_date             2021-10-21
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C12 H8 O6 S2), C12 H22 O2, C H6 N3'
_chemical_formula_sum            'C19 H32 N3 O5 S'
_chemical_formula_weight         414.53
_chemical_absolute_configuration -0.003(12)
_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 0.0181 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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   12.4527(2)
_cell_length_b                   13.4693(3)
_cell_length_c                   26.9148(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4514.40(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    15446
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.6310
_cell_measurement_theta_min      3.6480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.548
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1784
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            32043
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.834
_diffrn_reflns_theta_min         3.284
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  67.00   1.00    2.00    --   41.11 -99.00  30.00   66
  2  ω     23.00  65.00   1.00    2.00    --   41.11-125.00 -30.00   42
  3  ω     35.00 110.00   1.00    3.00    --  107.58 -61.00 -30.00   75
  4  ω     74.00 100.00   1.00    3.00    --  107.58 -94.00 -60.00   26
  5  ω     74.00 122.00   1.00    3.00    --  107.58-125.00-120.00   48
  6  ω     47.00 130.00   1.00    3.00    --  107.58 -61.00-150.00   83
  7  ω     80.00 177.00   1.00    3.00    --  107.58  30.00 -60.00   97
  8  ω    133.00 173.00   1.00    3.00    --  107.58  45.00-150.00   40
  9  ω    101.00 171.00   1.00    3.00    --  107.58 125.00-150.00   70
 10  ω     91.00 119.00   1.00    3.00    --  107.58  45.00-150.00   28
 11  ω     36.00 128.00   1.00    3.00    --  107.58 -15.00 -90.00   92
 12  ω     85.00 119.00   1.00    3.00    --  107.58-125.00  60.00   34
 13  ω     67.00 108.00   1.00    3.00    --  107.58 -94.00 120.00   41
 14  ω     53.00 132.00   1.00    3.00    --  107.58 -45.00 120.00   79
 15  ω     58.00  97.00   1.00    2.00    --   41.11-125.00 120.00   39
 16  ω     38.00  84.00   1.00    3.00    --  107.58 -45.00  60.00   46
 17  ω     25.00  61.00   1.00    3.00    --  107.58 -94.00-180.00   36
 18  ω    -36.00  -8.00   1.00    2.00    --  -41.11 125.00-150.00   28
 19  ω    -90.00 -54.00   1.00    2.00    --  -41.11 125.00-150.00   36
 20  ω   -114.00 -17.00   1.00    2.00    --  -41.11 -38.00  60.00   97
 21  ω   -118.00  -4.00   1.00    2.00    --  -41.11 -19.00 120.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0782330000
_diffrn_orient_matrix_UB_12      0.0551196000
_diffrn_orient_matrix_UB_13      -0.0347160000
_diffrn_orient_matrix_UB_21      0.0273452000
_diffrn_orient_matrix_UB_22      -0.0986796000
_diffrn_orient_matrix_UB_23      -0.0260553000
_diffrn_orient_matrix_UB_31      -0.0917675000
_diffrn_orient_matrix_UB_32      0.0174025000
_diffrn_orient_matrix_UB_33      -0.0373710000
_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'
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                8307
_reflns_number_total             8998
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 3355 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     513
_refine_ls_number_reflns         8998
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.067
_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)+(0.0606P)²+1.1082P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1139
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3A(H3A), C6A(H6A), C1A(H1A), C10A(H10A), C6B(H6B), C3B(H3B), C10B(H10B),
 C1B(H1B)
2.b Secondary CH2 refined with riding coordinates:
 C4A(H4AA,H4AB), C5A(H5AA,H5AB), C2A(H2AA,H2AB), C5B(H5BA,H5BB), C4B(H4BA,
 H4BB), C2B(H2BA,H2BB)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12)
2.d X=CH2 refined with riding coordinates:
 N1(H1C,H1D), N2(H2A,H2B), N3(H3C,H3D), N4(H4A,H4B), N5(H5A,H5B), N6(H6C,H6D)
2.e Idealised Me refined as rotating group:
 C9A(H9AA,H9AB,H9AC), C11A(H11A,H11B,H11C), C12A(H12A,H12B,H12C), C8A(H8AA,
 H8AB,H8AC), C9B(H9BA,H9BB,H9BC), C11B(H11D,H11E,H11F), C12B(H12D,H12E,H12F),
 C8B(H8BA,H8BB,H8BC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.75527(6) 0.83395(5) 0.57901(3) 0.02625(16) Uani 1 1 d . . . . .
S2 S 0.75137(6) 0.63758(5) 0.96048(3) 0.02672(16) Uani 1 1 d . . . . .
O1 O 0.86756(18) 0.83694(18) 0.56359(9) 0.0323(5) Uani 1 1 d . . . . .
O2 O 0.69577(18) 0.75565(17) 0.55378(9) 0.0317(5) Uani 1 1 d . . . . .
O3 O 0.70214(19) 0.93041(17) 0.57538(9) 0.0321(5) Uani 1 1 d . . . . .
O4 O 0.80645(19) 0.71619(18) 0.98727(9) 0.0327(5) Uani 1 1 d . . . . .
O5 O 0.80702(18) 0.54227(17) 0.96368(9) 0.0310(5) Uani 1 1 d . . . . .
O6 O 0.63876(18) 0.62968(18) 0.97481(9) 0.0315(5) Uani 1 1 d . . . . .
C1 C 0.7553(3) 0.8035(2) 0.64279(11) 0.0256(6) Uani 1 1 d . . . . .
C2 C 0.8411(3) 0.7540(2) 0.66369(12) 0.0303(7) Uani 1 1 d . . . . .
H2 H 0.899741 0.736641 0.644119 0.036 Uiso 1 1 calc R U . . .
C3 C 0.8403(3) 0.7301(3) 0.71352(13) 0.0315(7) Uani 1 1 d . . . . .
H3 H 0.898604 0.696672 0.727176 0.038 Uiso 1 1 calc R U . . .
C4 C 0.7538(3) 0.7550(2) 0.74368(11) 0.0273(6) Uani 1 1 d . . . . .
C5 C 0.6666(3) 0.8049(3) 0.72234(13) 0.0319(7) Uani 1 1 d . . . . .
H5 H 0.607900 0.821923 0.741904 0.038 Uiso 1 1 calc R U . . .
C6 C 0.6672(3) 0.8291(3) 0.67210(12) 0.0314(7) Uani 1 1 d . . . . .
H6 H 0.609021 0.862234 0.658112 0.038 Uiso 1 1 calc R U . . .
C7 C 0.7537(3) 0.7274(2) 0.79699(11) 0.0269(6) Uani 1 1 d . . . . .
C8 C 0.8009(3) 0.6389(2) 0.81241(12) 0.0307(7) Uani 1 1 d . . . . .
H8 H 0.833345 0.597742 0.789066 0.037 Uiso 1 1 calc R U . . .
C9 C 0.8003(3) 0.6110(2) 0.86225(12) 0.0292(7) Uani 1 1 d . . . . .
H9 H 0.831930 0.551584 0.872007 0.035 Uiso 1 1 calc R U . . .
C10 C 0.7525(3) 0.6720(2) 0.89718(11) 0.0264(6) Uani 1 1 d . . . . .
C11 C 0.7061(3) 0.7611(3) 0.88272(13) 0.0315(7) Uani 1 1 d . . . . .
H11 H 0.674566 0.802326 0.906298 0.038 Uiso 1 1 calc R U . . .
C12 C 0.7067(3) 0.7886(2) 0.83298(12) 0.0304(7) Uani 1 1 d . . . . .
H12 H 0.675429 0.848357 0.823460 0.036 Uiso 1 1 calc R U . . .
O2A O 0.5929(2) 0.1537(2) 0.59375(14) 0.0601(9) Uani 1 1 d . . . . .
O1A O 0.6077(2) 0.25979(19) 0.65819(10) 0.0398(6) Uani 1 1 d . . . . .
C9A C 0.9921(3) 0.3078(4) 0.63111(19) 0.0568(11) Uani 1 1 d . . . . .
H9AA H 1.046846 0.343017 0.613224 0.085 Uiso 1 1 calc R U . . .
H9AB H 0.996169 0.238394 0.623299 0.085 Uiso 1 1 calc R U . . .
H9AC H 1.002452 0.317008 0.666151 0.085 Uiso 1 1 calc R U . . .
C3A C 0.8822(3) 0.3476(3) 0.61628(14) 0.0388(8) Uani 1 1 d . . . . .
H3A H 0.875487 0.342976 0.580073 0.047 Uiso 1 1 calc R U . . .
C4A C 0.8673(3) 0.4562(3) 0.63137(17) 0.0459(9) Uani 1 1 d . . . . .
H4AA H 0.882590 0.463377 0.666518 0.055 Uiso 1 1 calc R U . . .
H4AB H 0.917810 0.497138 0.613148 0.055 Uiso 1 1 calc R U . . .
C5A C 0.7533(3) 0.4919(3) 0.62092(15) 0.0406(8) Uani 1 1 d . . . . .
H5AA H 0.739892 0.489146 0.585445 0.049 Uiso 1 1 calc R U . . .
H5AB H 0.746368 0.560482 0.631418 0.049 Uiso 1 1 calc R U . . .
C6A C 0.6693(3) 0.4288(3) 0.64798(13) 0.0326(7) Uani 1 1 d . . . . .
H6A H 0.688261 0.429466 0.683319 0.039 Uiso 1 1 calc R U . . .
C1A C 0.6819(3) 0.3220(2) 0.63005(12) 0.0303(7) Uani 1 1 d . . . . .
H1A H 0.665485 0.317819 0.594501 0.036 Uiso 1 1 calc R U . . .
C2A C 0.7946(3) 0.2837(3) 0.63977(13) 0.0342(7) Uani 1 1 d . . . . .
H2AA H 0.800360 0.216677 0.626894 0.041 Uiso 1 1 calc R U . . .
H2AB H 0.806326 0.280844 0.675366 0.041 Uiso 1 1 calc R U . . .
C10A C 0.5541(3) 0.4682(3) 0.64392(17) 0.0452(9) Uani 1 1 d . . . . .
H10A H 0.506652 0.418389 0.658789 0.054 Uiso 1 1 calc R U . . .
C11A C 0.5408(5) 0.5636(4) 0.6737(2) 0.0736(16) Uani 1 1 d . . . . .
H11A H 0.576373 0.617054 0.656793 0.110 Uiso 1 1 calc R U . . .
H11B H 0.571867 0.555098 0.706056 0.110 Uiso 1 1 calc R U . . .
H11C H 0.465813 0.578700 0.676981 0.110 Uiso 1 1 calc R U . . .
C12A C 0.5173(4) 0.4839(5) 0.5912(2) 0.0797(18) Uani 1 1 d . . . . .
H12A H 0.442815 0.502106 0.591050 0.120 Uiso 1 1 calc R U . . .
H12B H 0.526840 0.423599 0.572675 0.120 Uiso 1 1 calc R U . . .
H12C H 0.558938 0.535917 0.576228 0.120 Uiso 1 1 calc R U . . .
C7A C 0.5747(3) 0.1745(3) 0.63623(18) 0.0456(10) Uani 1 1 d . . . . .
C8A C 0.5146(4) 0.1107(3) 0.6724(2) 0.0673(15) Uani 1 1 d . . . . .
H8AA H 0.559569 0.056617 0.682764 0.101 Uiso 1 1 calc R U . . .
H8AB H 0.451221 0.084904 0.656702 0.101 Uiso 1 1 calc R U . . .
H8AC H 0.494604 0.149597 0.700765 0.101 Uiso 1 1 calc R U . . .
O2B O 0.9779(2) 0.0653(2) 0.75775(11) 0.0480(7) Uani 1 1 d . . . . .
O1B O 0.80544(19) 0.10903(18) 0.76795(8) 0.0314(5) Uani 1 1 d . . . . .
C6B C 0.7514(3) 0.2297(2) 0.82944(12) 0.0317(6) Uani 1 1 d . . . . .
H6B H 0.679664 0.199901 0.830062 0.038 Uiso 1 1 calc R U . . .
C5B C 0.7748(3) 0.2662(3) 0.88239(14) 0.0427(9) Uani 1 1 d . . . . .
H5BA H 0.846241 0.294881 0.883426 0.051 Uiso 1 1 calc R U . . .
H5BB H 0.723878 0.317813 0.891053 0.051 Uiso 1 1 calc R U . . .
C4B C 0.7677(3) 0.1835(3) 0.92021(13) 0.0451(9) Uani 1 1 d . . . . .
H4BA H 0.694408 0.159324 0.921604 0.054 Uiso 1 1 calc R U . . .
H4BB H 0.786022 0.209456 0.952742 0.054 Uiso 1 1 calc R U . . .
C3B C 0.8427(3) 0.0973(3) 0.90777(13) 0.0416(9) Uani 1 1 d . . . . .
H3B H 0.916739 0.121512 0.909840 0.050 Uiso 1 1 calc R U . . .
C9B C 0.8302(5) 0.0123(4) 0.94459(15) 0.0591(12) Uani 1 1 d . . . . .
H9BA H 0.838230 0.037106 0.977808 0.089 Uiso 1 1 calc R U . . .
H9BB H 0.884182 -0.037031 0.938261 0.089 Uiso 1 1 calc R U . . .
H9BC H 0.760316 -0.016929 0.940906 0.089 Uiso 1 1 calc R U . . .
C2B C 0.8227(3) 0.0619(3) 0.85448(13) 0.0359(8) Uani 1 1 d . . . . .
H2BA H 0.875235 0.011528 0.845940 0.043 Uiso 1 1 calc R U . . .
H2BB H 0.751995 0.032016 0.852408 0.043 Uiso 1 1 calc R U . . .
C10B C 0.7488(3) 0.3122(2) 0.78972(13) 0.0378(7) Uani 1 1 d . . . . .
H10B H 0.732585 0.280409 0.757846 0.045 Uiso 1 1 calc R U . . .
C11B C 0.8559(4) 0.3657(3) 0.78383(17) 0.0484(10) Uani 1 1 d . . . . .
H11D H 0.874820 0.397088 0.814620 0.073 Uiso 1 1 calc R U . . .
H11E H 0.849861 0.415004 0.758239 0.073 Uiso 1 1 calc R U . . .
H11F H 0.910465 0.318580 0.774909 0.073 Uiso 1 1 calc R U . . .
C12B C 0.6586(4) 0.3866(3) 0.80023(17) 0.0510(10) Uani 1 1 d . . . . .
H12D H 0.591784 0.351717 0.803687 0.077 Uiso 1 1 calc R U . . .
H12E H 0.653452 0.432866 0.773203 0.077 Uiso 1 1 calc R U . . .
H12F H 0.673983 0.421866 0.830404 0.077 Uiso 1 1 calc R U . . .
C1B C 0.8301(3) 0.1464(2) 0.81769(12) 0.0300(7) Uani 1 1 d . . . . .
H1B H 0.903378 0.173038 0.817941 0.036 Uiso 1 1 calc R U . . .
C7B C 0.8872(3) 0.0694(2) 0.74218(13) 0.0322(7) Uani 1 1 d . . . . .
C8B C 0.8521(4) 0.0295(3) 0.69319(14) 0.0436(9) Uani 1 1 d . . . . .
H8BA H 0.850998 -0.041713 0.694472 0.065 Uiso 1 1 calc R U . . .
H8BB H 0.901341 0.050784 0.667877 0.065 Uiso 1 1 calc R U . . .
H8BC H 0.781492 0.053711 0.685644 0.065 Uiso 1 1 calc R U . . .
N1 N 0.8014(2) 0.1161(2) 0.53547(12) 0.0340(6) Uani 1 1 d . . . . .
H1C H 0.768142 0.066753 0.548646 0.041 Uiso 1 1 calc R U . . .
H1D H 0.765943 0.167015 0.525314 0.041 Uiso 1 1 calc R U . . .
N2 N 0.9591(2) 0.1900(2) 0.51097(11) 0.0338(6) Uani 1 1 d . . . . .
H2A H 1.027847 0.188431 0.508279 0.041 Uiso 1 1 calc R U . . .
H2B H 0.923861 0.240992 0.500774 0.041 Uiso 1 1 calc R U . . .
N3 N 0.9621(2) 0.0355(2) 0.54640(12) 0.0361(7) Uani 1 1 d . . . . .
H3C H 1.030844 0.034378 0.543622 0.043 Uiso 1 1 calc R U . . .
H3D H 0.928843 -0.014148 0.559308 0.043 Uiso 1 1 calc R U . . .
C14 C 0.9073(3) 0.1138(2) 0.53080(12) 0.0293(7) Uani 1 1 d . . . . .
N4 N 0.9823(2) 0.7121(2) 0.48869(12) 0.0370(7) Uani 1 1 d . . . . .
H4A H 0.953256 0.757703 0.506559 0.044 Uiso 1 1 calc R U . . .
H4B H 1.044435 0.721799 0.475568 0.044 Uiso 1 1 calc R U . . .
N5 N 0.8356(2) 0.6122(2) 0.50171(11) 0.0345(6) Uani 1 1 d . . . . .
H5A H 0.802014 0.557355 0.496712 0.041 Uiso 1 1 calc R U . . .
H5B H 0.807209 0.657657 0.519898 0.041 Uiso 1 1 calc R U . . .
N6 N 0.9750(2) 0.5565(2) 0.45334(11) 0.0346(6) Uani 1 1 d . . . . .
H6C H 0.941247 0.501670 0.448389 0.042 Uiso 1 1 calc R U . . .
H6D H 1.037102 0.565724 0.440113 0.042 Uiso 1 1 calc R U . . .
C13 C 0.9314(3) 0.6267(2) 0.48137(12) 0.0292(7) Uani 1 1 d . . . . .


_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 O1 1.459(2) . ?
S1 O2 1.457(2) . ?
S1 O3 1.461(2) . ?
S1 C1 1.765(3) . ?
S2 O4 1.453(2) . ?
S2 O5 1.461(2) . ?
S2 O6 1.458(2) . ?
S2 C10 1.766(3) . ?
C1 C2 1.380(4) . ?
C1 C6 1.395(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(5) . ?
C4 C5 1.400(5) . ?
C4 C7 1.482(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.391(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.393(4) . ?
C7 C12 1.400(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.393(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(4) . ?
C10 C11 1.388(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.389(5) . ?
C12 H12 0.9300 . ?
O2A C7A 1.199(6) . ?
O1A C1A 1.459(4) . ?
O1A C7A 1.356(5) . ?
C9A H9AA 0.9600 . ?
C9A H9AB 0.9600 . ?
C9A H9AC 0.9600 . ?
C9A C3A 1.523(5) . ?
C3A H3A 0.9800 . ?
C3A C4A 1.529(6) . ?
C3A C2A 1.527(5) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4A C5A 1.525(6) . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C5A C6A 1.532(5) . ?
C6A H6A 0.9800 . ?
C6A C1A 1.525(5) . ?
C6A C10A 1.533(5) . ?
C1A H1A 0.9800 . ?
C1A C2A 1.517(5) . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C10A H10A 0.9800 . ?
C10A C11A 1.523(6) . ?
C10A C12A 1.506(7) . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C7A C8A 1.498(6) . ?
C8A H8AA 0.9600 . ?
C8A H8AB 0.9600 . ?
C8A H8AC 0.9600 . ?
O2B C7B 1.206(5) . ?
O1B C1B 1.463(4) . ?
O1B C7B 1.343(4) . ?
C6B H6B 0.9800 . ?
C6B C5B 1.535(5) . ?
C6B C10B 1.542(5) . ?
C6B C1B 1.523(5) . ?
C5B H5BA 0.9700 . ?
C5B H5BB 0.9700 . ?
C5B C4B 1.511(6) . ?
C4B H4BA 0.9700 . ?
C4B H4BB 0.9700 . ?
C4B C3B 1.527(6) . ?
C3B H3B 0.9800 . ?
C3B C9B 1.522(6) . ?
C3B C2B 1.532(5) . ?
C9B H9BA 0.9600 . ?
C9B H9BB 0.9600 . ?
C9B H9BC 0.9600 . ?
C2B H2BA 0.9700 . ?
C2B H2BB 0.9700 . ?
C2B C1B 1.512(5) . ?
C10B H10B 0.9800 . ?
C10B C11B 1.523(6) . ?
C10B C12B 1.532(5) . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?
C1B H1B 0.9800 . ?
C7B C8B 1.489(5) . ?
C8B H8BA 0.9600 . ?
C8B H8BB 0.9600 . ?
C8B H8BC 0.9600 . ?
N1 H1C 0.8600 . ?
N1 H1D 0.8600 . ?
N1 C14 1.325(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C14 1.324(4) . ?
N3 H3C 0.8600 . ?
N3 H3D 0.8600 . ?
N3 C14 1.323(4) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C13 1.328(4) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N5 C13 1.327(4) . ?
N6 H6C 0.8600 . ?
N6 H6D 0.8600 . ?
N6 C13 1.327(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
_geom_angle_publ_flag
O1 S1 O3 112.97(14) . . ?
O1 S1 C1 106.43(15) . . ?
O2 S1 O1 112.01(14) . . ?
O2 S1 O3 112.47(14) . . ?
O2 S1 C1 106.57(14) . . ?
O3 S1 C1 105.78(14) . . ?
O4 S2 O5 112.78(14) . . ?
O4 S2 O6 112.08(14) . . ?
O4 S2 C10 106.48(14) . . ?
O5 S2 C10 106.47(14) . . ?
O6 S2 O5 112.10(14) . . ?
O6 S2 C10 106.38(15) . . ?
C2 C1 S1 120.6(2) . . ?
C2 C1 C6 119.9(3) . . ?
C6 C1 S1 119.5(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 118.5(3) . . ?
C3 C4 C7 120.4(3) . . ?
C5 C4 C7 121.1(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 H6 120.2 . . ?
C8 C7 C4 120.2(3) . . ?
C8 C7 C12 118.3(3) . . ?
C12 C7 C4 121.5(3) . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C9 121.0(3) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 S2 120.2(2) . . ?
C9 C10 C11 120.2(3) . . ?
C11 C10 S2 119.6(2) . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.9(3) . . ?
C12 C11 H11 120.1 . . ?
C7 C12 H12 119.6 . . ?
C11 C12 C7 120.8(3) . . ?
C11 C12 H12 119.6 . . ?
C7A O1A C1A 116.9(3) . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C3A C9A H9AA 109.5 . . ?
C3A C9A H9AB 109.5 . . ?
C3A C9A H9AC 109.5 . . ?
C9A C3A H3A 108.4 . . ?
C9A C3A C4A 112.1(4) . . ?
C9A C3A C2A 109.6(3) . . ?
C4A C3A H3A 108.4 . . ?
C2A C3A H3A 108.4 . . ?
C2A C3A C4A 110.0(3) . . ?
C3A C4A H4AA 109.3 . . ?
C3A C4A H4AB 109.3 . . ?
H4AA C4A H4AB 108.0 . . ?
C5A C4A C3A 111.5(3) . . ?
C5A C4A H4AA 109.3 . . ?
C5A C4A H4AB 109.3 . . ?
C4A C5A H5AA 109.2 . . ?
C4A C5A H5AB 109.2 . . ?
C4A C5A C6A 111.9(3) . . ?
H5AA C5A H5AB 107.9 . . ?
C6A C5A H5AA 109.2 . . ?
C6A C5A H5AB 109.2 . . ?
C5A C6A H6A 106.9 . . ?
C5A C6A C10A 114.3(3) . . ?
C1A C6A C5A 107.6(3) . . ?
C1A C6A H6A 106.9 . . ?
C1A C6A C10A 113.6(3) . . ?
C10A C6A H6A 106.9 . . ?
O1A C1A C6A 108.2(3) . . ?
O1A C1A H1A 110.0 . . ?
O1A C1A C2A 107.5(3) . . ?
C6A C1A H1A 110.0 . . ?
C2A C1A C6A 111.2(3) . . ?
C2A C1A H1A 110.0 . . ?
C3A C2A H2AA 108.9 . . ?
C3A C2A H2AB 108.9 . . ?
C1A C2A C3A 113.5(3) . . ?
C1A C2A H2AA 108.9 . . ?
C1A C2A H2AB 108.9 . . ?
H2AA C2A H2AB 107.7 . . ?
C6A C10A H10A 107.3 . . ?
C11A C10A C6A 110.9(4) . . ?
C11A C10A H10A 107.3 . . ?
C12A C10A C6A 113.6(4) . . ?
C12A C10A H10A 107.3 . . ?
C12A C10A C11A 110.2(4) . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11B 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C10A C12A H12A 109.5 . . ?
C10A C12A H12B 109.5 . . ?
C10A C12A H12C 109.5 . . ?
H12A C12A H12B 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
O2A C7A O1A 123.8(4) . . ?
O2A C7A C8A 125.4(4) . . ?
O1A C7A C8A 110.8(4) . . ?
C7A C8A H8AA 109.5 . . ?
C7A C8A H8AB 109.5 . . ?
C7A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
C7B O1B C1B 116.8(3) . . ?
C5B C6B H6B 106.8 . . ?
C5B C6B C10B 114.7(3) . . ?
C10B C6B H6B 106.8 . . ?
C1B C6B H6B 106.8 . . ?
C1B C6B C5B 107.8(3) . . ?
C1B C6B C10B 113.6(3) . . ?
C6B C5B H5BA 109.2 . . ?
C6B C5B H5BB 109.2 . . ?
H5BA C5B H5BB 107.9 . . ?
C4B C5B C6B 112.2(3) . . ?
C4B C5B H5BA 109.2 . . ?
C4B C5B H5BB 109.2 . . ?
C5B C4B H4BA 109.2 . . ?
C5B C4B H4BB 109.2 . . ?
C5B C4B C3B 112.1(3) . . ?
H4BA C4B H4BB 107.9 . . ?
C3B C4B H4BA 109.2 . . ?
C3B C4B H4BB 109.2 . . ?
C4B C3B H3B 108.0 . . ?
C4B C3B C2B 110.0(3) . . ?
C9B C3B C4B 111.5(3) . . ?
C9B C3B H3B 108.0 . . ?
C9B C3B C2B 111.0(3) . . ?
C2B C3B H3B 108.0 . . ?
C3B C9B H9BA 109.5 . . ?
C3B C9B H9BB 109.5 . . ?
C3B C9B H9BC 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
C3B C2B H2BA 109.3 . . ?
C3B C2B H2BB 109.3 . . ?
H2BA C2B H2BB 107.9 . . ?
C1B C2B C3B 111.7(3) . . ?
C1B C2B H2BA 109.3 . . ?
C1B C2B H2BB 109.3 . . ?
C6B C10B H10B 107.2 . . ?
C11B C10B C6B 113.2(3) . . ?
C11B C10B H10B 107.2 . . ?
C11B C10B C12B 110.6(3) . . ?
C12B C10B C6B 111.0(3) . . ?
C12B C10B H10B 107.2 . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11E 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C10B C12B H12D 109.5 . . ?
C10B C12B H12E 109.5 . . ?
C10B C12B H12F 109.5 . . ?
H12D C12B H12E 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
O1B C1B C6B 108.0(3) . . ?
O1B C1B C2B 109.1(3) . . ?
O1B C1B H1B 109.1 . . ?
C6B C1B H1B 109.1 . . ?
C2B C1B C6B 112.3(3) . . ?
C2B C1B H1B 109.1 . . ?
O2B C7B O1B 123.3(3) . . ?
O2B C7B C8B 124.4(3) . . ?
O1B C7B C8B 112.2(3) . . ?
C7B C8B H8BA 109.5 . . ?
C7B C8B H8BB 109.5 . . ?
C7B C8B H8BC 109.5 . . ?
H8BA C8B H8BB 109.5 . . ?
H8BA C8B H8BC 109.5 . . ?
H8BB C8B H8BC 109.5 . . ?
H1C N1 H1D 120.0 . . ?
C14 N1 H1C 120.0 . . ?
C14 N1 H1D 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C14 N2 H2A 120.0 . . ?
C14 N2 H2B 120.0 . . ?
H3C N3 H3D 120.0 . . ?
C14 N3 H3C 120.0 . . ?
C14 N3 H3D 120.0 . . ?
N2 C14 N1 120.3(3) . . ?
N3 C14 N1 120.1(3) . . ?
N3 C14 N2 119.6(3) . . ?
H4A N4 H4B 120.0 . . ?
C13 N4 H4A 120.0 . . ?
C13 N4 H4B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C13 N5 H5A 120.0 . . ?
C13 N5 H5B 120.0 . . ?
H6C N6 H6D 120.0 . . ?
C13 N6 H6C 120.0 . . ?
C13 N6 H6D 120.0 . . ?
N5 C13 N4 119.7(3) . . ?
N5 C13 N6 119.8(3) . . ?
N6 C13 N4 120.4(3) . . ?

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 C1 C2 C3 -179.7(3) . . . . ?
S1 C1 C6 C5 179.7(3) . . . . ?
S2 C10 C11 C12 -180.0(3) . . . . ?
O1 S1 C1 C2 -23.5(3) . . . . ?
O1 S1 C1 C6 157.0(3) . . . . ?
O2 S1 C1 C2 96.2(3) . . . . ?
O2 S1 C1 C6 -83.3(3) . . . . ?
O3 S1 C1 C2 -143.9(3) . . . . ?
O3 S1 C1 C6 36.6(3) . . . . ?
O4 S2 C10 C9 120.8(3) . . . . ?
O4 S2 C10 C11 -58.6(3) . . . . ?
O5 S2 C10 C9 0.2(3) . . . . ?
O5 S2 C10 C11 -179.2(3) . . . . ?
O6 S2 C10 C9 -119.5(3) . . . . ?
O6 S2 C10 C11 61.1(3) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C2 C1 C6 C5 0.3(5) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C2 C3 C4 C7 179.1(3) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C3 C4 C7 C8 -34.6(5) . . . . ?
C3 C4 C7 C12 145.5(3) . . . . ?
C4 C5 C6 C1 0.0(5) . . . . ?
C4 C7 C8 C9 -179.1(3) . . . . ?
C4 C7 C12 C11 179.2(3) . . . . ?
C5 C4 C7 C8 144.2(3) . . . . ?
C5 C4 C7 C12 -35.6(5) . . . . ?
C6 C1 C2 C3 -0.3(5) . . . . ?
C7 C4 C5 C6 -179.1(3) . . . . ?
C7 C8 C9 C10 -0.2(5) . . . . ?
C8 C7 C12 C11 -0.7(5) . . . . ?
C8 C9 C10 S2 -179.9(3) . . . . ?
C8 C9 C10 C11 -0.5(5) . . . . ?
C9 C10 C11 C12 0.6(5) . . . . ?
C10 C11 C12 C7 0.0(5) . . . . ?
C12 C7 C8 C9 0.8(5) . . . . ?
O1A C1A C2A C3A -174.9(3) . . . . ?
C9A C3A C4A C5A -174.4(4) . . . . ?
C9A C3A C2A C1A 175.9(3) . . . . ?
C3A C4A C5A C6A 58.0(5) . . . . ?
C4A C3A C2A C1A 52.3(4) . . . . ?
C4A C5A C6A C1A -59.6(4) . . . . ?
C4A C5A C6A C10A 173.2(3) . . . . ?
C5A C6A C1A O1A 175.9(3) . . . . ?
C5A C6A C1A C2A 58.1(4) . . . . ?
C5A C6A C10A C11A -70.0(5) . . . . ?
C5A C6A C10A C12A 54.7(5) . . . . ?
C6A C1A C2A C3A -56.6(4) . . . . ?
C1A O1A C7A O2A -8.9(5) . . . . ?
C1A O1A C7A C8A 170.4(3) . . . . ?
C1A C6A C10A C11A 165.9(4) . . . . ?
C1A C6A C10A C12A -69.4(5) . . . . ?
C2A C3A C4A C5A -52.2(5) . . . . ?
C10A C6A C1A O1A -56.4(4) . . . . ?
C10A C6A C1A C2A -174.3(3) . . . . ?
C7A O1A C1A C6A 154.5(3) . . . . ?
C7A O1A C1A C2A -85.4(4) . . . . ?
C6B C5B C4B C3B 56.5(4) . . . . ?
C5B C6B C10B C11B 62.5(4) . . . . ?
C5B C6B C10B C12B -62.6(4) . . . . ?
C5B C6B C1B O1B 177.9(3) . . . . ?
C5B C6B C1B C2B 57.6(4) . . . . ?
C5B C4B C3B C9B -176.9(4) . . . . ?
C5B C4B C3B C2B -53.2(4) . . . . ?
C4B C3B C2B C1B 53.6(4) . . . . ?
C3B C2B C1B O1B -177.4(3) . . . . ?
C3B C2B C1B C6B -57.7(4) . . . . ?
C9B C3B C2B C1B 177.6(4) . . . . ?
C10B C6B C5B C4B 175.5(3) . . . . ?
C10B C6B C1B O1B -53.9(4) . . . . ?
C10B C6B C1B C2B -174.2(3) . . . . ?
C1B O1B C7B O2B -1.3(5) . . . . ?
C1B O1B C7B C8B 177.3(3) . . . . ?
C1B C6B C5B C4B -56.9(4) . . . . ?
C1B C6B C10B C11B -62.1(4) . . . . ?
C1B C6B C10B C12B 172.8(3) . . . . ?
C7B O1B C1B C6B 151.9(3) . . . . ?
C7B O1B C1B C2B -85.8(3) . . . . ?

_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 1.432
_oxdiff_exptl_absorpt_empirical_full_min 0.583
