# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_DTST
_database_code_depnum_ccdc_archive 'CCDC 2312419'
loop_
_audit_author_name
_audit_author_address
DTST
;SYSU
China
;
_audit_update_record             
;
2023-12-06 deposited with the CCDC.	2024-09-20 downloaded from the CCDC.
;
_audit_creation_date             2023-12-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        DTST
_chemical_formula_moiety         'C22 H10 N2 O4 S2, 2(C2 H5 N)'
_chemical_formula_sum            'C26 H20 N4 O4 S2'
_chemical_formula_weight         516.58
_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           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                   16.7130(15)
_cell_length_b                   8.6188(10)
_cell_length_c                   9.3560(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.976(9)
_cell_angle_gamma                90
_cell_volume                     1307.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1822
_cell_measurement_temperature    240.00(10)
_cell_measurement_theta_max      60.8850
_cell_measurement_theta_min      5.7340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.171
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_preparation       1
_exptl_crystal_recrystallization_method 1
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.575
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2593
_diffrn_reflns_point_group_measured_fraction_full 0.575
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         50.382
_diffrn_reflns_theta_min         5.814
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      240.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6525
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.575
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  32.00   1.00    7.50    --    0.00 -77.00 -90.00   52
  2  ω    -33.00   1.00   1.00    7.50    --    0.00  77.00 150.00   34
  3  ω     11.00  42.00   1.00    7.50    --    0.00  77.00 150.00   31
  4  ω     46.00 112.00   1.00   13.40    --   80.51-125.00 -30.00   66
  5  ω     22.00 105.00   1.00   13.40    --   80.51 -61.00 120.00   83
  6  ω    103.00 153.00   1.00   13.40    --   80.51  77.00 120.00   50
  7  ω    111.00 154.00   1.00   13.40    --   80.51 125.00  90.00   43
  8  ω     54.00 151.00   1.00   13.40    --   80.51  61.00 -90.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0908953000
_diffrn_orient_matrix_UB_12      -0.0415939000
_diffrn_orient_matrix_UB_13      0.0099236000
_diffrn_orient_matrix_UB_21      -0.0221288000
_diffrn_orient_matrix_UB_22      -0.1737983000
_diffrn_orient_matrix_UB_23      -0.0075463000
_diffrn_orient_matrix_UB_31      -0.0165399000
_diffrn_orient_matrix_UB_32      0.0054153000
_diffrn_orient_matrix_UB_33      -0.1691367000
_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                1202
_reflns_number_total             1363
_reflns_odcompleteness_completeness 98.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_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 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1363
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0659P)²+0.7600P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1310
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C-HB
 0.96 with sigma of 0.02
 C-HA
 0.96 with sigma of 0.02
 C00I-H00E
 0.96 with sigma of 0.02
 C00I-H00A
 0.96 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C004(H004), C006(H006), C009(H009), C00B(H00B), C00C(H00C)
3.b Idealised Me refined as rotating group:
 C00I(H00A,H00D,H00E)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
S001 S 0.97765(5) 0.65764(13) 0.68560(10) 0.0711(5) Uani 1 1 d . . . . .
N002 N 0.8126(2) 0.3187(4) 1.1318(4) 0.0759(10) Uani 1 1 d . . . . .
C003 C 0.98641(19) 0.5699(4) 0.8592(3) 0.0480(8) Uani 1 1 d . . . . .
C004 C 0.92174(19) 0.5034(4) 0.9061(3) 0.0495(9) Uani 1 1 d . . . . .
H004 H 0.8684 0.5045 0.8439 0.059 Uiso 1 1 calc R U . . .
C005 C 0.93523(18) 0.4349(4) 1.0443(3) 0.0460(8) Uani 1 1 d . . . . .
C006 C 0.7628(2) 0.5236(5) 0.4193(4) 0.0648(10) Uani 1 1 d . . . . .
H006 H 0.7451 0.4485 0.3456 0.078 Uiso 1 1 calc R U . . .
C007 C 0.8660(2) 0.3693(4) 1.0909(4) 0.0547(9) Uani 1 1 d . . . . .
C008 C 0.8715(2) 0.6407(4) 0.6001(4) 0.0542(10) Uani 1 1 d . . . . .
C009 C 0.7329(2) 0.7338(5) 0.5619(4) 0.0675(11) Uani 1 1 d . . . . .
H009 H 0.6947 0.8029 0.5863 0.081 Uiso 1 1 calc R U . . .
O00A O 0.5691(2) 0.7168(6) 0.3958(4) 0.1258(14) Uani 1 1 d . . . . .
C00B C 0.8450(2) 0.5306(4) 0.4918(4) 0.0590(10) Uani 1 1 d . . . . .
H00B H 0.8829 0.4608 0.4676 0.071 Uiso 1 1 calc R U . . .
C00C C 0.8148(2) 0.7428(5) 0.6352(4) 0.0632(10) Uani 1 1 d . . . . .
H00C H 0.8324 0.8180 0.7089 0.076 Uiso 1 1 calc R U . . .
C00D C 0.7063(2) 0.6245(5) 0.4531(4) 0.0611(10) Uani 1 1 d . . . . .
O00E O 0.5950(2) 0.5034(6) 0.2864(4) 0.1388(17) Uani 1 1 d . . . . .
C00F C 0.6158(3) 0.6136(8) 0.3710(5) 0.0920(16) Uani 1 1 d . . . . .
N00 N 0.4293(2) 0.5864(10) 0.1808(5) 0.186(3) Uani 1 1 d . . . . .
C C 0.4148(4) 0.6402(9) 0.0482(7) 0.128(2) Uani 1 1 d D . . . .
C00I C 0.3696(4) 0.5549(8) 0.2565(6) 0.151(3) Uani 1 1 d D . . . .
H00A H 0.3156 0.5576 0.1887 0.226 Uiso 1 1 calc DR U . . .
H00D H 0.3722 0.6321 0.3328 0.226 Uiso 1 1 calc R U . . .
H00E H 0.3792 0.4528 0.3010 0.226 Uiso 1 1 calc DR U . . .
HA H 0.3602(16) 0.638(6) -0.005(5) 0.123(18) Uiso 1 1 d D . . . .
HB H 0.461(2) 0.671(5) 0.024(5) 0.116(17) Uiso 1 1 d 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
S001 C003 1.765(3) . ?
S001 C008 1.768(4) . ?
N002 C007 1.139(4) . ?
C003 C004 1.385(4) . ?
C003 C005 1.400(4) 3_767 ?
C004 H004 0.9400 . ?
C004 C005 1.389(4) . ?
C005 C003 1.400(4) 3_767 ?
C005 C007 1.446(5) . ?
C006 H006 0.9400 . ?
C006 C00B 1.379(5) . ?
C006 C00D 1.376(5) . ?
C008 C00B 1.381(5) . ?
C008 C00C 1.389(5) . ?
C009 H009 0.9400 . ?
C009 C00C 1.378(5) . ?
C009 C00D 1.380(5) . ?
O00A C00F 1.241(6) . ?
C00B H00B 0.9400 . ?
C00C H00C 0.9400 . ?
C00D C00F 1.525(6) . ?
O00E C00F 1.231(6) . ?
N00 C 1.292(7) . ?
N00 C00I 1.382(7) . ?
C HA 0.93(2) . ?
C HB 0.90(2) . ?
C00I H00A 0.9700 . ?
C00I H00D 0.9700 . ?
C00I H00E 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C003 S001 C008 103.44(15) . . ?
C004 C003 S001 124.8(2) . . ?
C004 C003 C005 117.6(3) . 3_767 ?
C005 C003 S001 117.6(2) 3_767 . ?
C003 C004 H004 119.8 . . ?
C003 C004 C005 120.4(3) . . ?
C005 C004 H004 119.8 . . ?
C003 C005 C007 119.0(3) 3_767 . ?
C004 C005 C003 121.9(3) . 3_767 ?
C004 C005 C007 119.0(3) . . ?
C00B C006 H006 119.4 . . ?
C00D C006 H006 119.4 . . ?
C00D C006 C00B 121.1(4) . . ?
N002 C007 C005 178.0(4) . . ?
C00B C008 S001 119.8(3) . . ?
C00B C008 C00C 119.6(3) . . ?
C00C C008 S001 120.5(3) . . ?
C00C C009 H009 119.7 . . ?
C00C C009 C00D 120.7(3) . . ?
C00D C009 H009 119.7 . . ?
C006 C00B C008 119.7(3) . . ?
C006 C00B H00B 120.1 . . ?
C008 C00B H00B 120.1 . . ?
C008 C00C H00C 120.0 . . ?
C009 C00C C008 119.9(4) . . ?
C009 C00C H00C 120.0 . . ?
C006 C00D C009 119.0(3) . . ?
C006 C00D C00F 119.8(4) . . ?
C009 C00D C00F 121.2(4) . . ?
O00A C00F C00D 116.9(5) . . ?
O00E C00F O00A 125.5(5) . . ?
O00E C00F C00D 117.6(5) . . ?
C N00 C00I 124.9(5) . . ?
N00 C HA 116(3) . . ?
N00 C HB 112(3) . . ?
HA C HB 132(4) . . ?
N00 C00I H00A 109.5 . . ?
N00 C00I H00D 109.5 . . ?
N00 C00I H00E 109.5 . . ?
H00A C00I H00D 109.5 . . ?
H00A C00I H00E 109.5 . . ?
H00D C00I H00E 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
S001 C003 C004 C005 179.0(2) . . . . ?
S001 C008 C00B C006 -176.3(3) . . . . ?
S001 C008 C00C C009 176.4(3) . . . . ?
C003 S001 C008 C00B -104.1(3) . . . . ?
C003 S001 C008 C00C 79.3(3) . . . . ?
C003 C004 C005 C003 -0.1(5) . . . 3_767 ?
C003 C004 C005 C007 178.8(3) . . . . ?
C005 C003 C004 C005 0.1(5) 3_767 . . . ?
C006 C00D C00F O00A -173.2(4) . . . . ?
C006 C00D C00F O00E 7.1(6) . . . . ?
C008 S001 C003 C004 1.3(3) . . . . ?
C008 S001 C003 C005 -179.8(3) . . . 3_767 ?
C009 C00D C00F O00A 7.2(6) . . . . ?
C009 C00D C00F O00E -172.6(4) . . . . ?
C00B C006 C00D C009 -0.3(5) . . . . ?
C00B C006 C00D C00F -179.9(3) . . . . ?
C00B C008 C00C C009 -0.1(5) . . . . ?
C00C C008 C00B C006 0.3(5) . . . . ?
C00C C009 C00D C006 0.4(5) . . . . ?
C00C C009 C00D C00F -179.9(3) . . . . ?
C00D C006 C00B C008 -0.1(5) . . . . ?
C00D C009 C00C C008 -0.2(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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.457
_oxdiff_exptl_absorpt_empirical_full_min 0.762
# start Validation Reply Form
_vrf_THETM01_DTST                
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: We have used Cu radiation, long exposure time, and best
crystal to obtain best data set.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_DPDA
_database_code_depnum_ccdc_archive 'CCDC 2312421'
loop_
_audit_author_name
_audit_author_address
DPDA
;SYSU
China
;
_audit_update_record             
;
2023-12-06 deposited with the CCDC.	2024-09-20 downloaded from the CCDC.
;
_audit_creation_date             2023-12-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        DPDA
_chemical_formula_moiety         'C22 H12 N2 O6, C3 H6 N O'
_chemical_formula_sum            'C25 H18 N3 O7'
_chemical_formula_weight         472.42
_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'

_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.5890(5)
_cell_length_b                   13.1840(8)
_cell_length_c                   39.0756(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4424.9(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1629
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      40.6270
_cell_measurement_theta_min      2.2410
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.887
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear whiteish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1960
_exptl_crystal_preparation       1
_exptl_crystal_recrystallization_method 1
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_Laue_measured_fraction_full 0.344
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            6322
_diffrn_reflns_point_group_measured_fraction_full 0.344
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         41.083
_diffrn_reflns_theta_min         2.261
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.344
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     46.00  72.00   0.50    5.00    --   32.09-178.00 150.00   52
  2  ω     81.00 106.00   0.50    5.00    --   32.09-178.00 150.00   50
  3  ω     31.00  57.00   0.50    5.00    --   32.09 -82.00-164.00   52
  4  ω    -21.00  10.00   0.50    5.00    --   32.09 -82.00-164.00   62
  5  ω     18.00 105.00   0.50    5.00    --   32.09  38.00 -60.00  174
  6  ω    -24.00  43.00   0.50    5.00    --  -32.41  19.00-120.00  134
  7  ω     -4.00  37.00   0.50    5.00    --  -32.41  82.00 -43.00   82
  8  ω    -54.00 -10.00   0.50    5.00    --  -32.41  82.00 -43.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0152945000
_diffrn_orient_matrix_UB_12      0.0237500000
_diffrn_orient_matrix_UB_13      0.0384448000
_diffrn_orient_matrix_UB_21      0.0869486000
_diffrn_orient_matrix_UB_22      0.0989920000
_diffrn_orient_matrix_UB_23      -0.0086216000
_diffrn_orient_matrix_UB_31      -0.1561989000
_diffrn_orient_matrix_UB_32      0.0573562000
_diffrn_orient_matrix_UB_33      -0.0010487000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_special_details          1
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1051
_reflns_number_total             1380
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         1380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.042
_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)+(0.0938P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1362
_refine_special_details          1
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H33A,H33B,H33C} of C33, H16 of O16
 At 1.5 times of:
  {H34A,H34B,H34C} of C34, H25 of O25
2.a Riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C9(H9), C22(H22), C13(H13), C12(H12), C5(H5), C19(H19), C20(H20),
 C10(H10)
2.c Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C33(H33A,H33B,H33C)
2.d Idealised tetrahedral OH refined as rotating group:
 O25(H25)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O17 O 0.2218(4) 0.4623(3) 0.43490(13) 0.0281(12) Uani 1 1 d . . . . .
O15 O 0.0825(5) 0.1542(4) 0.67807(10) 0.0428(14) Uani 1 1 d . . . . .
N28 N 0.5014(6) 0.6979(4) 0.54836(13) 0.0345(17) Uani 1 1 d . . . . .
O7 O 0.2469(4) 0.5148(3) 0.57516(14) 0.0284(12) Uani 1 1 d . . . . .
C11 C 0.0924(8) 0.3154(6) 0.65022(19) 0.0229(17) Uani 1 1 d . . . . .
C8 C 0.1924(9) 0.4453(7) 0.59861(19) 0.0304(17) Uani 1 1 d . . . . .
C23 C 0.2398(7) 0.6338(7) 0.41337(17) 0.0303(18) Uani 1 1 d . . . . .
H23 H 0.1741 0.6577 0.4312 0.036 Uiso 1 1 calc R U . . .
C9 C 0.2424(7) 0.3454(7) 0.59917(18) 0.0307(17) Uani 1 1 d . . . . .
H9 H 0.3121 0.3213 0.5821 0.037 Uiso 1 1 calc R U . . .
C22 C 0.2941(8) 0.7006(5) 0.3884(2) 0.0271(18) Uani 1 1 d . . . . .
H22 H 0.2693 0.7707 0.3898 0.032 Uiso 1 1 calc R U . . .
C13 C 0.0943(8) 0.4814(5) 0.6239(2) 0.0282(18) Uani 1 1 d . . . . .
H13 H 0.0611 0.5502 0.6237 0.034 Uiso 1 1 calc R U . . .
C12 C 0.0447(7) 0.4160(7) 0.64951(17) 0.0299(17) Uani 1 1 d . . . . .
H12 H -0.0229 0.4406 0.6669 0.036 Uiso 1 1 calc R U . . .
C21 C 0.3845(8) 0.6649(6) 0.36150(18) 0.0214(17) Uani 1 1 d . . . . .
C5 C 0.3235(7) 0.5533(5) 0.4849(2) 0.0231(16) Uani 1 1 d . . . . .
H5 H 0.3836 0.5985 0.4713 0.028 Uiso 1 1 calc R U . . .
C29 C 0.0553(9) 0.3357(6) 0.47468(17) 0.028(2) Uani 1 1 d . . . . .
C3 C 0.1486(8) 0.4136(5) 0.4901(2) 0.0240(17) Uani 1 1 d . . . . .
C2 C 0.1486(7) 0.4216(5) 0.5257(2) 0.0281(17) Uani 1 1 d . . . . .
H2 H 0.1648 0.3621 0.5352 0.034 Uiso 1 1 d R U . . .
C18 C 0.2817(8) 0.5333(7) 0.4121(2) 0.0265(17) Uani 1 1 d . . . . .
C1 C 0.2403(9) 0.4962(6) 0.5406(2) 0.0220(16) Uani 1 1 d . . . . .
C6 C 0.3265(8) 0.5605(5) 0.5203(2) 0.0210(16) Uani 1 1 d . . . . .
C19 C 0.3754(8) 0.4970(5) 0.3862(2) 0.0313(18) Uani 1 1 d . . . . .
H19 H 0.4056 0.4277 0.3858 0.038 Uiso 1 1 calc R U . . .
C20 C 0.4253(7) 0.5628(7) 0.36065(16) 0.0281(17) Uani 1 1 d . . . . .
H20 H 0.4878 0.5378 0.3425 0.034 Uiso 1 1 calc R U . . .
C4 C 0.2325(8) 0.4800(6) 0.4695(2) 0.0235(16) Uani 1 1 d . . . . .
O26 O 0.4310(5) 0.8284(4) 0.33828(9) 0.0373(13) Uani 1 1 d . . . . .
O30 O 0.0863(5) 0.6825(4) 0.74037(9) 0.0405(13) Uani 1 1 d . . . . .
O16 O -0.0399(6) 0.2871(3) 0.70172(13) 0.0443(14) Uani 1 1 d . . . . .
H16 H -0.056(7) 0.255(4) 0.7208(16) 0.053 Uiso 1 1 d . U . . .
C34 C 0.2214(7) 0.5345(4) 0.78284(16) 0.0446(19) Uani 1 1 d . . . . .
H34A H 0.3186 0.5671 0.7900 0.067 Uiso 1 1 calc R U . . .
H34B H 0.2187 0.4648 0.7915 0.067 Uiso 1 1 calc R U . . .
H34C H 0.1327 0.5725 0.7921 0.067 Uiso 1 1 calc R U . . .
N32 N 0.2126(6) 0.5331(4) 0.74537(12) 0.0306(14) Uani 1 1 d . . . . .
C31 C 0.1480(8) 0.6056(6) 0.72698(18) 0.039(2) Uani 1 1 d . . . . .
O25 O 0.4881(5) 0.6919(3) 0.30681(11) 0.0424(13) Uani 1 1 d . . . . .
H25 H 0.5104 0.7360 0.2921 0.064 Uiso 1 1 calc R U . . .
C27 C 0.4220(8) 0.6371(6) 0.53608(17) 0.027(2) Uani 1 1 d . . . . .
C C 0.0470(8) 0.2437(6) 0.67751(17) 0.0317(19) Uani 1 1 d . . . . .
C24 C 0.4372(7) 0.7371(6) 0.33509(18) 0.0299(18) Uani 1 1 d . . . . .
C33 C 0.2921(7) 0.4481(5) 0.72910(15) 0.047(2) Uani 1 1 d . . . . .
H33A H 0.2814 0.4535 0.7042 0.057 Uiso 1 1 calc R U . . .
H33B H 0.2457 0.3843 0.7369 0.057 Uiso 1 1 calc R U . . .
H33C H 0.4027 0.4495 0.7352 0.057 Uiso 1 1 calc R U . . .
C10 C 0.1899(8) 0.2801(5) 0.6249(2) 0.0288(18) Uani 1 1 d . . . . .
H10 H 0.2217 0.2111 0.6250 0.035 Uiso 1 1 calc R U . . .
N1 N -0.0197(7) 0.2722(4) 0.46244(13) 0.0352(17) 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
O17 C18 1.392(7) . ?
O17 C4 1.377(7) . ?
O15 C 1.218(7) . ?
N28 C27 1.156(8) . ?
O7 C8 1.378(7) . ?
O7 C1 1.374(7) . ?
C11 C12 1.389(7) . ?
C11 C 1.477(9) . ?
C11 C10 1.376(7) . ?
C8 C9 1.386(8) . ?
C8 C13 1.382(8) . ?
C23 H23 0.9500 . ?
C23 C22 1.394(7) . ?
C23 C18 1.374(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.399(8) . ?
C22 H22 0.9500 . ?
C22 C21 1.389(7) . ?
C13 H13 0.9500 . ?
C13 C12 1.389(7) . ?
C12 H12 0.9500 . ?
C21 C20 1.391(7) . ?
C21 C24 1.475(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(7) . ?
C5 C4 1.380(8) . ?
C29 C3 1.435(10) . ?
C29 N1 1.160(8) . ?
C3 C2 1.395(7) . ?
C3 C4 1.389(8) . ?
C2 H2 0.8795 . ?
C2 C1 1.388(8) . ?
C18 C19 1.379(8) . ?
C1 C6 1.378(8) . ?
C6 C27 1.440(9) . ?
C19 H19 0.9500 . ?
C19 C20 1.390(8) . ?
C20 H20 0.9500 . ?
O26 C24 1.211(7) . ?
O30 C31 1.258(7) . ?
O16 H16 0.87(6) . ?
O16 C 1.334(8) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C34 N32 1.466(7) . ?
N32 C31 1.319(7) . ?
N32 C33 1.458(7) . ?
O25 H25 0.8400 . ?
O25 C24 1.330(7) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C10 H10 0.9500 . ?

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
C4 O17 C18 119.3(5) . . ?
C1 O7 C8 121.4(5) . . ?
C12 C11 C 123.2(8) . . ?
C10 C11 C12 119.2(6) . . ?
C10 C11 C 117.6(8) . . ?
O7 C8 C9 122.5(8) . . ?
O7 C8 C13 116.9(8) . . ?
C13 C8 C9 120.3(7) . . ?
C22 C23 H23 120.1 . . ?
C18 C23 H23 120.1 . . ?
C18 C23 C22 119.8(6) . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.7(6) . . ?
C10 C9 H9 120.1 . . ?
C23 C22 H22 119.9 . . ?
C21 C22 C23 120.1(6) . . ?
C21 C22 H22 119.9 . . ?
C8 C13 H13 120.4 . . ?
C8 C13 C12 119.2(6) . . ?
C12 C13 H13 120.4 . . ?
C11 C12 C13 121.1(6) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C22 C21 C20 119.1(6) . . ?
C22 C21 C24 118.8(7) . . ?
C20 C21 C24 122.0(8) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.4(6) . . ?
N1 C29 C3 179.4(8) . . ?
C2 C3 C29 118.2(9) . . ?
C4 C3 C29 119.8(8) . . ?
C4 C3 C2 122.0(6) . . ?
C3 C2 H2 110.9 . . ?
C1 C2 C3 118.1(6) . . ?
C1 C2 H2 111.3 . . ?
C23 C18 O17 122.0(8) . . ?
C23 C18 C19 121.0(6) . . ?
C19 C18 O17 116.8(8) . . ?
O7 C1 C2 124.2(8) . . ?
O7 C1 C6 115.7(8) . . ?
C6 C1 C2 120.0(6) . . ?
C5 C6 C27 119.1(8) . . ?
C1 C6 C5 121.5(6) . . ?
C1 C6 C27 119.4(8) . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.3(6) . . ?
C20 C19 H19 120.3 . . ?
C21 C20 H20 119.7 . . ?
C19 C20 C21 120.6(6) . . ?
C19 C20 H20 119.7 . . ?
O17 C4 C5 125.7(8) . . ?
O17 C4 C3 115.3(8) . . ?
C5 C4 C3 118.9(6) . . ?
C O16 H16 119(4) . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N32 C34 H34A 109.5 . . ?
N32 C34 H34B 109.5 . . ?
N32 C34 H34C 109.5 . . ?
C31 N32 C34 123.8(5) . . ?
C31 N32 C33 121.1(6) . . ?
C33 N32 C34 114.9(5) . . ?
O30 C31 N32 122.3(6) . . ?
C24 O25 H25 109.5 . . ?
N28 C27 C6 178.5(7) . . ?
O15 C C11 124.5(7) . . ?
O15 C O16 122.9(6) . . ?
O16 C C11 112.6(7) . . ?
O26 C24 C21 123.8(6) . . ?
O26 C24 O25 123.1(6) . . ?
O25 C24 C21 113.1(6) . . ?
N32 C33 H33A 109.5 . . ?
N32 C33 H33B 109.5 . . ?
N32 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C11 C10 C9 120.4(6) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?

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
O17 C18 C19 C20 173.4(5) . . . . ?
O7 C8 C9 C10 176.1(5) . . . . ?
O7 C8 C13 C12 -175.5(5) . . . . ?
O7 C1 C6 C5 -176.6(5) . . . . ?
O7 C1 C6 C27 3.4(8) . . . . ?
C8 O7 C1 C2 16.1(8) . . . . ?
C8 O7 C1 C6 -167.0(5) . . . . ?
C8 C9 C10 C11 -1.8(8) . . . . ?
C8 C13 C12 C11 0.1(8) . . . . ?
C23 C22 C21 C20 -2.8(8) . . . . ?
C23 C22 C21 C24 178.6(5) . . . . ?
C23 C18 C19 C20 -1.4(8) . . . . ?
C9 C8 C13 C12 -0.9(8) . . . . ?
C22 C23 C18 O17 -175.3(5) . . . . ?
C22 C23 C18 C19 -0.8(8) . . . . ?
C22 C21 C20 C19 0.5(8) . . . . ?
C22 C21 C24 O26 13.8(9) . . . . ?
C22 C21 C24 O25 -164.3(5) . . . . ?
C13 C8 C9 C10 1.7(8) . . . . ?
C12 C11 C O15 177.2(5) . . . . ?
C12 C11 C O16 -2.0(8) . . . . ?
C12 C11 C10 C9 1.1(8) . . . . ?
C29 C3 C2 C1 179.3(5) . . . . ?
C29 C3 C4 O17 -2.1(7) . . . . ?
C29 C3 C4 C5 -178.9(5) . . . . ?
C3 C2 C1 O7 177.6(5) . . . . ?
C3 C2 C1 C6 0.8(8) . . . . ?
C2 C3 C4 O17 179.6(5) . . . . ?
C2 C3 C4 C5 2.8(8) . . . . ?
C2 C1 C6 C5 0.5(8) . . . . ?
C2 C1 C6 C27 -179.6(5) . . . . ?
C18 O17 C4 C5 -13.1(8) . . . . ?
C18 O17 C4 C3 170.3(5) . . . . ?
C18 C23 C22 C21 2.9(8) . . . . ?
C18 C19 C20 C21 1.5(8) . . . . ?
C1 O7 C8 C9 54.2(7) . . . . ?
C1 O7 C8 C13 -131.3(5) . . . . ?
C6 C5 C4 O17 -177.9(5) . . . . ?
C6 C5 C4 C3 -1.5(8) . . . . ?
C20 C21 C24 O26 -164.8(5) . . . . ?
C20 C21 C24 O25 17.1(8) . . . . ?
C4 O17 C18 C23 -53.3(7) . . . . ?
C4 O17 C18 C19 132.0(5) . . . . ?
C4 C5 C6 C1 -0.1(8) . . . . ?
C4 C5 C6 C27 179.9(5) . . . . ?
C4 C3 C2 C1 -2.4(8) . . . . ?
C34 N32 C31 O30 -0.8(9) . . . . ?
C C11 C12 C13 178.0(5) . . . . ?
C C11 C10 C9 -177.3(5) . . . . ?
C24 C21 C20 C19 179.1(5) . . . . ?
C33 N32 C31 O30 -176.0(5) . . . . ?
C10 C11 C12 C13 -0.2(8) . . . . ?
C10 C11 C O15 -4.5(9) . . . . ?
C10 C11 C O16 176.3(5) . . . . ?

_olex2_exptl_crystal_mounting_method 1
_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 1.447
_oxdiff_exptl_absorpt_empirical_full_min 0.713
# start Validation Reply Form
_vrf_THETM01_DPDA                
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: We have used Cu radiation, long exposure time, and best
crystal to obtain best data set.
;
_vrf_PLAT088_DPDA                
;
PROBLEM: Poor Data / Parameter Ratio ....................       4.29 Note  
RESPONSE: We have used Cu radiation, long exposure time, and best
crystal to obtain best data set, there is not diffraction points observed when t
resolution high than 1.2.
;
# end Validation Reply Form
