# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_20190357
_database_code_depnum_ccdc_archive 'CCDC 2007793'
loop_
_audit_author_name
_audit_author_address
'Jian-Qiang Zhao'
;Chengdu University
China
;
_audit_update_record             
;
2020-06-03 deposited with the CCDC.	2020-08-28 downloaded from the CCDC.
;
_audit_creation_date             2019-03-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H21 N O5 S2'
_chemical_formula_sum            'C22 H21 N O5 S2'
_chemical_formula_weight         443.52
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4S2
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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.71695(13)
_cell_length_b                   13.36161(18)
_cell_length_c                   17.6913(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2060.55(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11357
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9570
_cell_measurement_theta_min      4.1410
_shelx_estimated_absorpt_T_max   0.778
_shelx_estimated_absorpt_T_min   0.692
_exptl_absorpt_coefficient_mu    2.645
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19546
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.065
_diffrn_reflns_theta_min         4.146
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -101.00  -37.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000   30.0000 128

#__ type_ start__ end____ width___ exp.time_
  2 omega -108.00  -83.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -150.0000 50

#__ type_ start__ end____ width___ exp.time_
  3 omega  -76.00  -43.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -150.0000 66

#__ type_ start__ end____ width___ exp.time_
  4 omega  -33.00   -6.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000   30.0000 54

#__ type_ start__ end____ width___ exp.time_
  5 omega -100.00  -41.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  150.0000 118

#__ type_ start__ end____ width___ exp.time_
  6 omega   74.00  100.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  120.0000 52

#__ type_ start__ end____ width___ exp.time_
  7 omega  -32.00   58.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000 -150.0000 180

#__ type_ start__ end____ width___ exp.time_
  8 omega   -9.00   16.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  108.0000  -20.8188 50

#__ type_ start__ end____ width___ exp.time_
  9 omega    9.00   59.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -90.0000 100

#__ type_ start__ end____ width___ exp.time_
 10 omega   14.00  106.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000  -30.0000 184

#__ type_ start__ end____ width___ exp.time_
 11 omega   37.00   70.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000   90.0000 66

#__ type_ start__ end____ width___ exp.time_
 12 omega   57.00  106.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 98

#__ type_ start__ end____ width___ exp.time_
 13 omega   -4.00   49.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000   60.0000 106

#__ type_ start__ end____ width___ exp.time_
 14 omega   -9.00   16.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  108.0000   52.3759 50

#__ type_ start__ end____ width___ exp.time_
 15 omega   26.00   52.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -120.0000 52

#__ type_ start__ end____ width___ exp.time_
 16 omega   31.00   57.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -60.0000 52

#__ type_ start__ end____ width___ exp.time_
 17 omega   69.00   96.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 54

#__ type_ start__ end____ width___ exp.time_
 18 omega    3.00   29.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000  120.0000 52

#__ type_ start__ end____ width___ exp.time_
 19 omega   29.00   90.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000    0.0000 122

#__ type_ start__ end____ width___ exp.time_
 20 omega   79.00  109.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 60

#__ type_ start__ end____ width___ exp.time_
 21 omega  107.00  177.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 140

#__ type_ start__ end____ width___ exp.time_
 22 omega   37.00   88.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 102

#__ type_ start__ end____ width___ exp.time_
 23 omega   60.00   88.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 56

#__ type_ start__ end____ width___ exp.time_
 24 omega   82.00  161.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   60.0000 158

#__ type_ start__ end____ width___ exp.time_
 25 omega   88.00  114.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 52

#__ type_ start__ end____ width___ exp.time_
 26 omega   82.00  108.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -60.0000 52

#__ type_ start__ end____ width___ exp.time_
 27 omega   90.00  119.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 58

#__ type_ start__ end____ width___ exp.time_
 28 omega  141.00  173.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 64

#__ type_ start__ end____ width___ exp.time_
 29 omega   82.00  114.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   30.0000 64

#__ type_ start__ end____ width___ exp.time_
 30 omega   83.00  115.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 64

#__ type_ start__ end____ width___ exp.time_
 31 omega  122.00  160.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 76

#__ type_ start__ end____ width___ exp.time_
 32 omega   87.00  113.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   65.0000  -75.2507 52

#__ type_ start__ end____ width___ exp.time_
 33 omega  122.00  175.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 106

#__ type_ start__ end____ width___ exp.time_
 34 omega   79.00  104.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 50

#__ type_ start__ end____ width___ exp.time_
 35 omega  148.00  175.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 54

#__ type_ start__ end____ width___ exp.time_
 36 omega   79.00  170.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 182

#__ type_ start__ end____ width___ exp.time_
 37 omega  102.00  178.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 152

#__ type_ start__ end____ width___ exp.time_
 38 omega   88.00  114.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 52

#__ type_ start__ end____ width___ exp.time_
 39 omega   79.00  104.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 50

#__ type_ start__ end____ width___ exp.time_
 40 omega   87.00  113.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 52

#__ type_ start__ end____ width___ exp.time_
 41 omega   79.00  105.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 52

#__ type_ start__ end____ width___ exp.time_
 42 omega   88.00  114.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 52

#__ type_ start__ end____ width___ exp.time_
 43 omega   88.00  114.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 52

#__ type_ start__ end____ width___ exp.time_
 44 omega   88.00  114.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 52

#__ type_ start__ end____ width___ exp.time_
 45 omega   88.00  114.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 52

#__ type_ start__ end____ width___ exp.time_
 46 omega   91.00  116.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -120.0000 50

#__ type_ start__ end____ width___ exp.time_
 47 omega   79.00  171.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 184

#__ type_ start__ end____ width___ exp.time_
 48 omega   89.00  114.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 50

#__ type_ start__ end____ width___ exp.time_
 49 omega  120.00  153.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 66

#__ type_ start__ end____ width___ exp.time_
 50 omega  116.00  157.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 82

#__ type_ start__ end____ width___ exp.time_
 51 omega  100.00  173.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 146

#__ type_ start__ end____ width___ exp.time_
 52 omega   79.00  105.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   26.0000  -71.9268 52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0558471000
_diffrn_orient_matrix_UB_12      -0.0964207000
_diffrn_orient_matrix_UB_13      0.0389073000
_diffrn_orient_matrix_UB_21      0.0399668000
_diffrn_orient_matrix_UB_22      0.0452475000
_diffrn_orient_matrix_UB_23      0.0777097000
_diffrn_orient_matrix_UB_31      -0.1628260000
_diffrn_orient_matrix_UB_32      0.0441364000
_diffrn_orient_matrix_UB_33      0.0056937000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                3862
_reflns_number_total             3953
_reflns_odcompleteness_completeness 99.91
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1569 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.013(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3953
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.090
_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)+(0.0634P)²+0.1988P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.0996
_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, All O(H) groups
2.a Riding coordinates:
 O3(H3A)
2.b Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C9(H9)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C14(H14), C15(H15), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
C1 C 0.2853(5) 0.1341(3) 0.3781(2) 0.0624(10) Uani 1 1 d . . . . .
H1 H 0.3555 0.1783 0.3568 0.075 Uiso 1 1 calc R . . . .
C2 C 0.1944(7) 0.0745(4) 0.3326(3) 0.0773(14) Uani 1 1 d . . . . .
H2 H 0.2041 0.0787 0.2803 0.093 Uiso 1 1 calc R . . . .
C3 C 0.0888(6) 0.0087(4) 0.3635(3) 0.0766(15) Uani 1 1 d . . . . .
H3 H 0.0278 -0.0299 0.3317 0.092 Uiso 1 1 calc R . . . .
C4 C 0.0728(5) -0.0006(3) 0.4414(3) 0.0664(11) Uani 1 1 d . . . . .
H4 H 0.0031 -0.0451 0.4628 0.080 Uiso 1 1 calc R . . . .
C5 C 0.1657(4) 0.0594(2) 0.4857(2) 0.0489(7) Uani 1 1 d . . . . .
C6 C 0.2702(4) 0.1270(2) 0.45565(19) 0.0453(7) Uani 1 1 d . . . . .
C7 C 0.3590(3) 0.1864(2) 0.51390(17) 0.0406(6) Uani 1 1 d . . . . .
H7 H 0.4643 0.1964 0.4960 0.049 Uiso 1 1 calc R . . . .
C8 C 0.3612(4) 0.1219(2) 0.58473(19) 0.0439(6) Uani 1 1 d . . . . .
H8 H 0.4360 0.0687 0.5749 0.053 Uiso 1 1 calc R . . . .
C9 C 0.4065(4) 0.1677(2) 0.6605(2) 0.0521(8) Uani 1 1 d . . . . .
H9 H 0.3666 0.1243 0.7006 0.062 Uiso 1 1 calc R . . . .
C10 C 0.3411(3) 0.2693(2) 0.67179(17) 0.0390(6) Uani 1 1 d . . . . .
C11 C 0.2759(3) 0.32853(19) 0.61888(14) 0.0335(5) Uani 1 1 d . . . . .
C12 C 0.3327(3) 0.3209(2) 0.74266(16) 0.0409(6) Uani 1 1 d . . . . .
C13 C 0.2536(4) 0.4110(2) 0.73137(15) 0.0373(5) Uani 1 1 d . . . . .
C14 C 0.2191(4) 0.4755(2) 0.79081(17) 0.0487(7) Uani 1 1 d . . . . .
H14 H 0.1610 0.5330 0.7835 0.058 Uiso 1 1 calc R . . . .
C15 C 0.2758(5) 0.4496(3) 0.86158(18) 0.0588(9) Uani 1 1 d . . . . .
H15 H 0.2556 0.4911 0.9026 0.071 Uiso 1 1 calc R . . . .
C16 C 0.3618(5) 0.3634(3) 0.8724(2) 0.0638(10) Uani 1 1 d . . . . .
H16 H 0.4017 0.3498 0.9201 0.077 Uiso 1 1 calc R . . . .
C17 C 0.3892(4) 0.2978(3) 0.8142(2) 0.0545(8) Uani 1 1 d . . . . .
H17 H 0.4443 0.2392 0.8224 0.065 Uiso 1 1 calc R . . . .
C18 C 0.1585(3) 0.4963(2) 0.61234(16) 0.0360(6) Uani 1 1 d . . . . .
C19 C 0.0868(4) 0.6722(2) 0.62877(18) 0.0447(7) Uani 1 1 d . . . . .
C20 C -0.0642(5) 0.6645(3) 0.5863(3) 0.0674(10) Uani 1 1 d . . . . .
H20A H -0.0988 0.7303 0.5728 0.101 Uiso 1 1 calc GR . . . .
H20B H -0.1394 0.6328 0.6179 0.101 Uiso 1 1 calc GR . . . .
H20C H -0.0497 0.6254 0.5413 0.101 Uiso 1 1 calc GR . . . .
C21 C 0.2153(5) 0.7125(3) 0.5798(2) 0.0606(9) Uani 1 1 d . . . . .
H21A H 0.1926 0.7802 0.5655 0.091 Uiso 1 1 calc GR . . . .
H21B H 0.2249 0.6719 0.5353 0.091 Uiso 1 1 calc GR . . . .
H21C H 0.3098 0.7109 0.6076 0.091 Uiso 1 1 calc GR . . . .
C22 C 0.0731(7) 0.7332(3) 0.7008(2) 0.0741(13) Uani 1 1 d . . . . .
H22A H 0.1689 0.7316 0.7276 0.111 Uiso 1 1 calc GR . . . .
H22B H -0.0062 0.7055 0.7321 0.111 Uiso 1 1 calc GR . . . .
H22C H 0.0480 0.8012 0.6883 0.111 Uiso 1 1 calc GR . . . .
N1 N 0.2188(3) 0.41597(16) 0.65306(13) 0.0347(5) Uani 1 1 d . . . . .
O1 O 0.0599(3) 0.1271(2) 0.61655(17) 0.0621(7) Uani 1 1 d . . . . .
O2 O 0.1862(5) -0.0377(2) 0.6159(2) 0.0841(10) Uani 1 1 d . . . . .
O3 O 0.5663(4) 0.1724(3) 0.6683(2) 0.0841(10) Uani 1 1 d . . . . .
H3A H 0.6244 0.1581 0.6210 0.126 Uiso 1 1 d R . . . .
O4 O 0.1365(3) 0.49241(17) 0.54519(12) 0.0493(5) Uani 1 1 d . . . . .
O5 O 0.1329(3) 0.57255(17) 0.65783(12) 0.0516(6) Uani 1 1 d . . . . .
S1 S 0.17478(10) 0.06135(6) 0.58548(5) 0.0503(2) Uani 1 1 d . . . . .
S2 S 0.26194(8) 0.30883(5) 0.52148(3) 0.03640(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
C1 H1 0.9300 . ?
C1 C2 1.381(7) . ?
C1 C6 1.382(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(5) . ?
C5 C6 1.388(5) . ?
C5 S1 1.768(4) . ?
C6 C7 1.513(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.521(4) . ?
C7 S2 1.847(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.525(5) . ?
C8 S1 1.815(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.487(4) . ?
C9 O3 1.401(5) . ?
C10 C11 1.351(4) . ?
C10 C12 1.432(4) . ?
C11 N1 1.407(3) . ?
C11 S2 1.747(3) . ?
C12 C13 1.402(4) . ?
C12 C17 1.392(4) . ?
C13 C14 1.392(4) . ?
C13 N1 1.420(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.389(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.388(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.373(6) . ?
C17 H17 0.9300 . ?
C18 N1 1.396(4) . ?
C18 O4 1.205(4) . ?
C18 O5 1.317(4) . ?
C19 C20 1.519(5) . ?
C19 C21 1.515(5) . ?
C19 C22 1.518(5) . ?
C19 O5 1.483(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O1 S1 1.441(3) . ?
O2 S1 1.432(3) . ?
O3 H3A 0.9962 . ?

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
C2 C1 H1 120.5 . . ?
C2 C1 C6 119.0(4) . . ?
C6 C1 H1 120.5 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.1(4) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.0(4) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 121.6 . . ?
C5 C4 C3 116.7(4) . . ?
C5 C4 H4 121.6 . . ?
C4 C5 C6 123.1(4) . . ?
C4 C5 S1 126.8(3) . . ?
C6 C5 S1 110.1(2) . . ?
C1 C6 C5 119.1(3) . . ?
C1 C6 C7 126.3(3) . . ?
C5 C6 C7 114.6(3) . . ?
C6 C7 H7 109.3 . . ?
C6 C7 C8 105.7(3) . . ?
C6 C7 S2 106.25(19) . . ?
C8 C7 H7 109.3 . . ?
C8 C7 S2 116.6(2) . . ?
S2 C7 H7 109.3 . . ?
C7 C8 H8 105.9 . . ?
C7 C8 C9 120.0(3) . . ?
C7 C8 S1 104.3(2) . . ?
C9 C8 H8 105.9 . . ?
C9 C8 S1 113.8(3) . . ?
S1 C8 H8 105.9 . . ?
C8 C9 H9 107.9 . . ?
C10 C9 C8 112.7(3) . . ?
C10 C9 H9 107.9 . . ?
O3 C9 C8 111.2(3) . . ?
O3 C9 H9 107.9 . . ?
O3 C9 C10 109.1(3) . . ?
C11 C10 C9 127.1(3) . . ?
C11 C10 C12 107.7(3) . . ?
C12 C10 C9 125.2(3) . . ?
C10 C11 N1 109.7(2) . . ?
C10 C11 S2 128.6(2) . . ?
N1 C11 S2 121.63(19) . . ?
C13 C12 C10 108.3(2) . . ?
C17 C12 C10 132.2(3) . . ?
C17 C12 C13 119.6(3) . . ?
C12 C13 N1 106.5(2) . . ?
C14 C13 C12 122.0(3) . . ?
C14 C13 N1 131.4(3) . . ?
C13 C14 H14 121.6 . . ?
C15 C14 C13 116.8(3) . . ?
C15 C14 H14 121.6 . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.5(3) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.3(3) . . ?
C17 C16 H16 119.3 . . ?
C12 C17 H17 120.7 . . ?
C16 C17 C12 118.6(4) . . ?
C16 C17 H17 120.7 . . ?
O4 C18 N1 122.4(3) . . ?
O4 C18 O5 127.5(3) . . ?
O5 C18 N1 110.1(2) . . ?
C21 C19 C20 112.4(3) . . ?
C21 C19 C22 110.3(3) . . ?
C22 C19 C20 112.6(3) . . ?
O5 C19 C20 110.2(3) . . ?
O5 C19 C21 108.5(3) . . ?
O5 C19 C22 102.3(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C11 N1 C13 107.8(2) . . ?
C18 N1 C11 123.4(2) . . ?
C18 N1 C13 128.3(2) . . ?
C9 O3 H3A 114.5 . . ?
C18 O5 C19 121.9(2) . . ?
C5 S1 C8 92.23(16) . . ?
O1 S1 C5 111.03(17) . . ?
O1 S1 C8 110.69(15) . . ?
O2 S1 C5 111.4(2) . . ?
O2 S1 C8 110.6(2) . . ?
O2 S1 O1 117.9(2) . . ?
C11 S2 C7 99.97(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A S2 1.00 2.83 3.774(5) 159.1 3_556

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
C1 C2 C3 C4 -1.0(7) . . . . ?
C1 C6 C7 C8 -153.7(3) . . . . ?
C1 C6 C7 S2 81.8(4) . . . . ?
C2 C1 C6 C5 0.8(5) . . . . ?
C2 C1 C6 C7 -179.6(3) . . . . ?
C2 C3 C4 C5 0.7(6) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C3 C4 C5 S1 -178.0(3) . . . . ?
C4 C5 C6 C1 -1.2(5) . . . . ?
C4 C5 C6 C7 179.2(3) . . . . ?
C4 C5 S1 C8 160.8(3) . . . . ?
C4 C5 S1 O1 -86.0(3) . . . . ?
C4 C5 S1 O2 47.6(4) . . . . ?
C5 C6 C7 C8 25.9(3) . . . . ?
C5 C6 C7 S2 -98.7(3) . . . . ?
C6 C1 C2 C3 0.3(6) . . . . ?
C6 C5 S1 C8 -17.8(2) . . . . ?
C6 C5 S1 O1 95.4(3) . . . . ?
C6 C5 S1 O2 -131.0(3) . . . . ?
C6 C7 C8 C9 -165.1(3) . . . . ?
C6 C7 C8 S1 -36.2(3) . . . . ?
C6 C7 S2 C11 141.3(2) . . . . ?
C7 C8 C9 C10 40.9(4) . . . . ?
C7 C8 C9 O3 -82.0(4) . . . . ?
C7 C8 S1 C5 31.6(2) . . . . ?
C7 C8 S1 O1 -81.9(2) . . . . ?
C7 C8 S1 O2 145.4(2) . . . . ?
C8 C7 S2 C11 23.8(2) . . . . ?
C8 C9 C10 C11 -13.6(5) . . . . ?
C8 C9 C10 C12 164.5(3) . . . . ?
C9 C8 S1 C5 164.1(2) . . . . ?
C9 C8 S1 O1 50.6(3) . . . . ?
C9 C8 S1 O2 -82.0(3) . . . . ?
C9 C10 C11 N1 175.9(3) . . . . ?
C9 C10 C11 S2 -5.5(5) . . . . ?
C9 C10 C12 C13 -175.6(3) . . . . ?
C9 C10 C12 C17 5.9(6) . . . . ?
C10 C11 N1 C13 1.2(3) . . . . ?
C10 C11 N1 C18 173.4(3) . . . . ?
C10 C11 S2 C7 0.4(3) . . . . ?
C10 C12 C13 C14 176.3(3) . . . . ?
C10 C12 C13 N1 -2.1(3) . . . . ?
C10 C12 C17 C16 -179.9(3) . . . . ?
C11 C10 C12 C13 2.8(3) . . . . ?
C11 C10 C12 C17 -175.7(3) . . . . ?
C12 C10 C11 N1 -2.4(3) . . . . ?
C12 C10 C11 S2 176.1(2) . . . . ?
C12 C13 C14 C15 4.2(5) . . . . ?
C12 C13 N1 C11 0.6(3) . . . . ?
C12 C13 N1 C18 -171.2(3) . . . . ?
C13 C12 C17 C16 1.8(5) . . . . ?
C13 C14 C15 C16 -0.4(5) . . . . ?
C14 C13 N1 C11 -177.5(3) . . . . ?
C14 C13 N1 C18 10.7(5) . . . . ?
C14 C15 C16 C17 -2.7(6) . . . . ?
C15 C16 C17 C12 2.0(6) . . . . ?
C17 C12 C13 C14 -5.0(5) . . . . ?
C17 C12 C13 N1 176.7(3) . . . . ?
C20 C19 O5 C18 60.7(4) . . . . ?
C21 C19 O5 C18 -62.8(4) . . . . ?
C22 C19 O5 C18 -179.4(3) . . . . ?
N1 C11 S2 C7 178.8(2) . . . . ?
N1 C13 C14 C15 -177.9(3) . . . . ?
N1 C18 O5 C19 172.4(3) . . . . ?
O3 C9 C10 C11 110.5(4) . . . . ?
O3 C9 C10 C12 -71.4(4) . . . . ?
O4 C18 N1 C11 7.8(4) . . . . ?
O4 C18 N1 C13 178.4(3) . . . . ?
O4 C18 O5 C19 -7.1(5) . . . . ?
O5 C18 N1 C11 -171.7(3) . . . . ?
O5 C18 N1 C13 -1.1(4) . . . . ?
S1 C5 C6 C1 177.5(3) . . . . ?
S1 C5 C6 C7 -2.1(3) . . . . ?
S1 C8 C9 C10 -83.7(3) . . . . ?
S1 C8 C9 O3 153.5(3) . . . . ?
S2 C7 C8 C9 -47.4(4) . . . . ?
S2 C7 C8 S1 81.6(2) . . . . ?
S2 C11 N1 C13 -177.5(2) . . . . ?
S2 C11 N1 C18 -5.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_201906159
_database_code_depnum_ccdc_archive 'CCDC 2007795'
loop_
_audit_author_name
_audit_author_address
'Jian-Qiang Zhao'
;Chengdu University
China
;
_audit_update_record             
;
2020-06-03 deposited with the CCDC.	2020-08-28 downloaded from the CCDC.
;
_audit_creation_date             2019-06-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 O3 S2'
_chemical_formula_sum            'C15 H12 O3 S2'
_chemical_formula_weight         304.37
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O1S1P1
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'
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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.8266(4)
_cell_length_b                   13.1360(6)
_cell_length_c                   13.1894(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1356.00(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2088
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3430
_cell_measurement_theta_min      3.3530
_shelx_estimated_absorpt_T_max   0.715
_shelx_estimated_absorpt_T_min   0.533
_exptl_absorpt_coefficient_mu    3.601
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.491
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4921
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.060
_diffrn_reflns_theta_max         67.060
_diffrn_reflns_theta_min         4.751
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -108.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000    0.0000 76

#__ type_ start__ end____ width___ exp.time_
  2 omega  -62.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000 -180.0000 98

#__ type_ start__ end____ width___ exp.time_
  3 omega  -57.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega -101.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -150.0000 85

#__ type_ start__ end____ width___ exp.time_
  5 omega   47.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000  -90.0000 31

#__ type_ start__ end____ width___ exp.time_
  6 omega  -22.00    8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
  7 omega    0.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000  -90.0000 31

#__ type_ start__ end____ width___ exp.time_
  8 omega   76.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
  9 omega   28.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000  -30.0000 37

#__ type_ start__ end____ width___ exp.time_
 10 omega   65.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 44

#__ type_ start__ end____ width___ exp.time_
 11 omega   45.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 49

#__ type_ start__ end____ width___ exp.time_
 12 omega   44.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 47

#__ type_ start__ end____ width___ exp.time_
 13 omega   62.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   49.00   74.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 15 omega   60.00   99.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 39

#__ type_ start__ end____ width___ exp.time_
 16 omega   39.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 70

#__ type_ start__ end____ width___ exp.time_
 17 omega   88.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   46.00  153.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  -30.0000 107
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0158641000
_diffrn_orient_matrix_UB_12      0.1132950000
_diffrn_orient_matrix_UB_13      0.0287258000
_diffrn_orient_matrix_UB_21      0.0045044000
_diffrn_orient_matrix_UB_22      -0.0287840000
_diffrn_orient_matrix_UB_23      0.1131721000
_diffrn_orient_matrix_UB_31      0.1961672000
_diffrn_orient_matrix_UB_32      0.0098306000
_diffrn_orient_matrix_UB_33      -0.0001550000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2210
_reflns_number_total             2433
_reflns_odcompleteness_completeness 99.93
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 
;
 Flack x determined using 852 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.010(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.063
_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)+(0.0574P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1030
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C13(H13), C14(H14), C15(H15)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;
_atom_sites_solution_hydrogens   geom
_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
C1 C -0.0535(7) 0.5015(4) 0.1329(4) 0.0548(12) Uani 1 1 d . . . . .
H1 H -0.0001 0.5057 0.0700 0.066 Uiso 1 1 calc R . . . .
C2 C -0.2190(7) 0.4659(4) 0.1404(4) 0.0624(14) Uani 1 1 d . . . . .
H2 H -0.2770 0.4463 0.0820 0.075 Uiso 1 1 calc R . . . .
C3 C -0.3003(7) 0.4587(4) 0.2338(4) 0.0578(13) Uani 1 1 d . . . . .
H3 H -0.4125 0.4356 0.2371 0.069 Uiso 1 1 calc R . . . .
C4 C -0.2169(6) 0.4852(3) 0.3204(4) 0.0512(12) Uani 1 1 d . . . . .
H4 H -0.2695 0.4792 0.3834 0.061 Uiso 1 1 calc R . . . .
C5 C -0.0509(6) 0.5213(3) 0.3118(3) 0.0397(9) Uani 1 1 d . . . . .
C6 C 0.0321(6) 0.5310(3) 0.2197(3) 0.0395(9) Uani 1 1 d . . . . .
C7 C 0.2098(5) 0.5732(3) 0.2228(3) 0.0360(8) Uani 1 1 d . . . . .
H7 H 0.2863 0.5270 0.1862 0.043 Uiso 1 1 calc R . . . .
C8 C 0.2693(5) 0.5807(3) 0.3346(3) 0.0337(8) Uani 1 1 d . . . . .
H8 H 0.3441 0.5225 0.3484 0.040 Uiso 1 1 calc R . . . .
C9 C 0.3658(6) 0.6777(3) 0.3645(3) 0.0371(9) Uani 1 1 d . . . . .
H9 H 0.2820 0.7320 0.3757 0.044 Uiso 1 1 calc R . . . .
C10 C 0.4889(6) 0.7126(3) 0.2839(3) 0.0393(9) Uani 1 1 d . . . . .
C11 C 0.4272(6) 0.7272(3) 0.1852(3) 0.0410(9) Uani 1 1 d . . . . .
C12 C 0.5338(7) 0.7660(4) 0.1104(4) 0.0553(12) Uani 1 1 d . . . . .
H12 H 0.4940 0.7737 0.0444 0.066 Uiso 1 1 calc R . . . .
C13 C 0.6985(7) 0.7929(4) 0.1345(4) 0.0593(13) Uani 1 1 d . . . . .
H13 H 0.7690 0.8207 0.0850 0.071 Uiso 1 1 calc R . . . .
C14 C 0.7602(6) 0.7791(4) 0.2312(5) 0.0609(14) Uani 1 1 d . . . . .
H14 H 0.8721 0.7973 0.2465 0.073 Uiso 1 1 calc R . . . .
C15 C 0.6567(6) 0.7385(4) 0.3055(4) 0.0488(11) Uani 1 1 d . . . . .
H15 H 0.6998 0.7285 0.3705 0.059 Uiso 1 1 calc R . . . .
O1 O 0.0995(4) 0.4905(3) 0.4892(3) 0.0597(9) Uani 1 1 d . . . . .
O2 O 0.0129(5) 0.6645(3) 0.4423(3) 0.0573(9) Uani 1 1 d . . . . .
O3 O 0.4429(6) 0.6544(2) 0.4581(2) 0.0603(10) Uani 1 1 d . . . . .
H3A H 0.4677 0.7073 0.4876 0.090 Uiso 1 1 calc GR . . . .
S1 S 0.07724(13) 0.56598(8) 0.41139(7) 0.0397(3) Uani 1 1 d . . . . .
S2 S 0.21131(15) 0.69758(9) 0.16023(8) 0.0456(3) 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
C1 H1 0.9300 . ?
C1 C2 1.381(7) . ?
C1 C6 1.382(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.361(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(7) . ?
C5 C6 1.383(6) . ?
C5 S1 1.753(4) . ?
C6 C7 1.498(6) . ?
C7 H7 0.9800 . ?
C7 C8 1.549(5) . ?
C7 S2 1.831(4) . ?
C8 H8 0.9800 . ?
C8 C9 1.533(5) . ?
C8 S1 1.823(4) . ?
C9 H9 0.9800 . ?
C9 C10 1.506(6) . ?
C9 O3 1.408(5) . ?
C10 C11 1.402(6) . ?
C10 C15 1.387(6) . ?
C11 C12 1.389(6) . ?
C11 S2 1.765(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.374(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(8) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(7) . ?
C15 H15 0.9300 . ?
O1 S1 1.438(3) . ?
O2 S1 1.447(3) . ?
O3 H3A 0.8200 . ?

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
C2 C1 H1 120.3 . . ?
C2 C1 C6 119.3(5) . . ?
C6 C1 H1 120.3 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.0(5) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.5(5) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 121.1 . . ?
C3 C4 C5 117.9(5) . . ?
C5 C4 H4 121.1 . . ?
C4 C5 S1 126.1(4) . . ?
C6 C5 C4 122.9(4) . . ?
C6 C5 S1 111.0(3) . . ?
C1 C6 C5 118.3(4) . . ?
C1 C6 C7 125.2(4) . . ?
C5 C6 C7 116.5(4) . . ?
C6 C7 H7 109.0 . . ?
C6 C7 C8 109.2(3) . . ?
C6 C7 S2 108.9(3) . . ?
C8 C7 H7 109.0 . . ?
C8 C7 S2 111.7(3) . . ?
S2 C7 H7 109.0 . . ?
C7 C8 H8 107.8 . . ?
C7 C8 S1 105.9(3) . . ?
C9 C8 C7 116.5(3) . . ?
C9 C8 H8 107.8 . . ?
C9 C8 S1 110.6(3) . . ?
S1 C8 H8 107.8 . . ?
C8 C9 H9 108.3 . . ?
C10 C9 C8 112.7(3) . . ?
C10 C9 H9 108.3 . . ?
O3 C9 C8 104.8(3) . . ?
O3 C9 H9 108.3 . . ?
O3 C9 C10 114.3(4) . . ?
C11 C10 C9 118.5(4) . . ?
C15 C10 C9 122.4(4) . . ?
C15 C10 C11 118.9(4) . . ?
C10 C11 S2 118.2(3) . . ?
C12 C11 C10 120.2(4) . . ?
C12 C11 S2 121.6(4) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.5(5) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.7(5) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.3(5) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.4(5) . . ?
C14 C15 H15 119.8 . . ?
C9 O3 H3A 109.5 . . ?
C5 S1 C8 95.24(19) . . ?
O1 S1 C5 111.9(2) . . ?
O1 S1 C8 111.73(19) . . ?
O1 S1 O2 117.2(2) . . ?
O2 S1 C5 108.1(2) . . ?
O2 S1 C8 110.4(2) . . ?
C11 S2 C7 96.8(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A O2 0.82 1.95 2.772(4) 176.7 3_566

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
C1 C2 C3 C4 -1.1(8) . . . . ?
C1 C6 C7 C8 -171.2(4) . . . . ?
C1 C6 C7 S2 66.6(5) . . . . ?
C2 C1 C6 C5 1.5(7) . . . . ?
C2 C1 C6 C7 -178.6(5) . . . . ?
C2 C3 C4 C5 1.4(7) . . . . ?
C3 C4 C5 C6 -0.2(7) . . . . ?
C3 C4 C5 S1 176.5(4) . . . . ?
C4 C5 C6 C1 -1.2(7) . . . . ?
C4 C5 C6 C7 178.8(4) . . . . ?
C4 C5 S1 C8 173.6(4) . . . . ?
C4 C5 S1 O1 57.7(5) . . . . ?
C4 C5 S1 O2 -72.9(5) . . . . ?
C5 C6 C7 C8 8.8(5) . . . . ?
C5 C6 C7 S2 -113.4(4) . . . . ?
C6 C1 C2 C3 -0.3(8) . . . . ?
C6 C5 S1 C8 -9.3(3) . . . . ?
C6 C5 S1 O1 -125.2(3) . . . . ?
C6 C5 S1 O2 104.2(3) . . . . ?
C6 C7 C8 C9 -137.7(4) . . . . ?
C6 C7 C8 S1 -14.3(4) . . . . ?
C6 C7 S2 C11 176.1(3) . . . . ?
C7 C8 C9 C10 -40.0(5) . . . . ?
C7 C8 C9 O3 -164.9(3) . . . . ?
C7 C8 S1 C5 13.6(3) . . . . ?
C7 C8 S1 O1 129.7(3) . . . . ?
C7 C8 S1 O2 -98.0(3) . . . . ?
C8 C7 S2 C11 55.4(3) . . . . ?
C8 C9 C10 C11 53.8(5) . . . . ?
C8 C9 C10 C15 -131.5(4) . . . . ?
C9 C8 S1 C5 140.6(3) . . . . ?
C9 C8 S1 O1 -103.3(3) . . . . ?
C9 C8 S1 O2 29.0(3) . . . . ?
C9 C10 C11 C12 175.6(4) . . . . ?
C9 C10 C11 S2 -3.1(5) . . . . ?
C9 C10 C15 C14 -173.9(4) . . . . ?
C10 C11 C12 C13 -2.0(7) . . . . ?
C10 C11 S2 C7 -47.2(4) . . . . ?
C11 C10 C15 C14 0.8(7) . . . . ?
C11 C12 C13 C14 1.8(8) . . . . ?
C12 C11 S2 C7 134.2(4) . . . . ?
C12 C13 C14 C15 -0.4(8) . . . . ?
C13 C14 C15 C10 -0.9(7) . . . . ?
C15 C10 C11 C12 0.7(7) . . . . ?
C15 C10 C11 S2 -178.0(3) . . . . ?
O3 C9 C10 C11 173.3(4) . . . . ?
O3 C9 C10 C15 -12.0(6) . . . . ?
S1 C5 C6 C1 -178.4(4) . . . . ?
S1 C5 C6 C7 1.6(5) . . . . ?
S1 C8 C9 C10 -161.0(3) . . . . ?
S1 C8 C9 O3 74.2(4) . . . . ?
S2 C7 C8 C9 -17.2(4) . . . . ?
S2 C7 C8 S1 106.2(3) . . . . ?
S2 C11 C12 C13 176.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
