# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_201912329
_database_code_depnum_ccdc_archive 'CCDC 2003750'
loop_
_audit_author_name
_audit_author_address
HanLiLi
;zhengzhou university
China
;
_audit_update_record             
;
2020-05-13 deposited with the CCDC.	2021-04-02 downloaded from the CCDC.
;
_audit_creation_date             2019-12-22
_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         'C20 H16 N2 O2 S'
_chemical_formula_sum            'C20 H16 N2 O2 S'
_chemical_formula_weight         348.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         C40H40O2N4S1
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                   9.2243(9)
_cell_length_b                   9.2775(13)
_cell_length_c                   11.9174(11)
_cell_angle_alpha                109.972(11)
_cell_angle_beta                 100.537(9)
_cell_angle_gamma                108.093(11)
_cell_volume                     862.17(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1533
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4950
_cell_measurement_theta_min      4.1570
_shelx_estimated_absorpt_T_max   0.870
_shelx_estimated_absorpt_T_min   0.775
_exptl_absorpt_coefficient_mu    1.794
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6330
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.921
_diffrn_reflns_theta_min         4.171
_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 0.995
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -15.00   1.00    1.00    --  -33.50 -57.00-180.00   87
  2  ω    -62.00  36.00   1.00    1.00    --  -33.50  77.00 -60.00   98
  3  ω     -4.00  77.00   1.00    1.00    --   36.47 -99.00  30.00   81
  4  ω     -4.00  77.00   1.00    1.00    --   36.47 -99.00 -90.00   81
  5  ω     14.00 107.00   1.00    1.00    --   36.47  37.00  90.00   93
  6  ω     -4.00  77.00   1.00    1.00    --   36.47 -99.00 150.00   81
  7  ω     22.00  76.00   1.00    1.00    --   36.47  57.00  90.00   54
  8  ω     20.00  84.00   1.00    1.00    --   36.47  57.00-120.00   64
  9  ω     58.00  96.00   1.00    1.00    --   36.47 178.00 120.00   38
 10  ω    -32.00  40.00   1.00    1.00    --   36.47 -37.00  90.00   72
 11  ω     92.00 122.00   1.00    2.50    --  108.00 -61.00 150.00   30
 12  ω     40.00  84.00   1.00    2.50    --  108.00 -61.00 150.00   44
 13  ω    122.00 177.00   1.00    2.50    --  108.00  30.00-180.00   55
 14  ω     79.00 136.00   1.00    2.50    --  108.00 -77.00 -30.00   57
 15  ω     41.00  72.00   1.00    2.50    --  108.00 -94.00  90.00   31
 16  ω     37.00 104.00   1.00    2.50    --  108.00-111.00 -90.00   67
 17  ω     39.00 112.00   1.00    2.50    --  108.00-111.00 -30.00   73
 18  ω     41.00 104.00   1.00    2.50    --  108.00 -94.00 150.00   63
 19  ω    128.00 173.00   1.00    2.50    --  108.00  61.00   0.00   45
 20  ω     61.00 126.00   1.00    2.50    --  108.00 -61.00 -90.00   65
 21  ω    126.00 164.00   1.00    2.50    --  108.00  61.00  90.00   38
 22  ω     88.00 119.00   1.00    2.50    --  108.00  61.00   0.00   31
 23  ω     88.00 121.00   1.00    2.50    --  108.00  61.00  90.00   33
 24  ω     68.00 109.00   1.00    2.50    --  108.00-111.00 120.00   41
 25  ω    130.00 176.00   1.00    2.50    --  108.00  45.00 120.00   46
 26  ω     89.00 173.00   1.00    2.50    --  108.00  45.00  60.00   84
 27  ω     45.00  71.00   1.00    2.50    --  108.00 -45.00 150.00   26
 28  ω    103.00 128.00   1.00    2.50    --  108.00 -45.00 150.00   25
 29  ω     37.00 104.00   1.00    2.50    --  108.00 -30.00  60.00   67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0823452000
_diffrn_orient_matrix_UB_12      -0.1236728000
_diffrn_orient_matrix_UB_13      -0.0252707000
_diffrn_orient_matrix_UB_21      0.1663626000
_diffrn_orient_matrix_UB_22      0.1483175000
_diffrn_orient_matrix_UB_23      0.0615356000
_diffrn_orient_matrix_UB_31      0.0044491000
_diffrn_orient_matrix_UB_32      -0.0021932000
_diffrn_orient_matrix_UB_33      0.1292478000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2455
_reflns_number_total             3249
_reflns_odcompleteness_completeness 99.58
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0098(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.035
_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)+(0.0588P)²+0.0977P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1408
_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.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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
S1 S 0.13811(8) 0.45815(9) 0.29924(6) 0.0539(2) Uani 1 1 d . . . . .
O1 O 0.0972(3) 0.4157(3) 0.39792(17) 0.0664(5) Uani 1 1 d . . . . .
O2 O 0.2601(2) 0.4173(3) 0.25461(18) 0.0675(6) Uani 1 1 d . . . . .
N1 N -0.1877(3) 0.3357(3) 0.1846(2) 0.0542(5) Uani 1 1 d . . . . .
N2 N -0.2274(3) 0.1924(3) -0.0211(2) 0.0574(6) Uani 1 1 d . . . . .
C1 C -0.2359(4) 0.3938(4) 0.2879(3) 0.0687(8) Uani 1 1 d . . . . .
H1 H -0.1605 0.4597 0.3681 0.082 Uiso 1 1 calc R . . . .
C2 C -0.3946(4) 0.3533(4) 0.2704(4) 0.0794(10) Uani 1 1 d . . . . .
H2 H -0.4280 0.3929 0.3396 0.095 Uiso 1 1 calc R . . . .
C3 C -0.5097(4) 0.2536(4) 0.1511(4) 0.0827(10) Uani 1 1 d . . . . .
H3 H -0.6183 0.2276 0.1415 0.099 Uiso 1 1 calc R . . . .
C4 C -0.4639(4) 0.1948(4) 0.0496(3) 0.0713(8) Uani 1 1 d . . . . .
H4 H -0.5407 0.1279 -0.0299 0.086 Uiso 1 1 calc R . . . .
C5 C -0.2991(3) 0.2352(3) 0.0649(3) 0.0581(7) Uani 1 1 d . . . . .
C6 C -0.0376(3) 0.3570(3) 0.1696(2) 0.0504(6) Uani 1 1 d . . . . .
C7 C -0.0678(3) 0.2674(3) 0.0412(2) 0.0505(6) Uani 1 1 d . . . . .
C8 C 0.0446(3) 0.2457(3) -0.0310(2) 0.0522(6) Uani 1 1 d . . . . .
C9 C 0.0155(4) 0.0857(4) -0.1158(3) 0.0621(7) Uani 1 1 d . . . . .
H9 H -0.0704 -0.0061 -0.1233 0.075 Uiso 1 1 calc R . . . .
C10 C 0.1137(4) 0.0621(4) -0.1895(3) 0.0716(8) Uani 1 1 d . . . . .
H10 H 0.0954 -0.0456 -0.2446 0.086 Uiso 1 1 calc R . . . .
C11 C 0.2382(4) 0.1981(4) -0.1811(3) 0.0713(9) Uani 1 1 d . . . . .
H11 H 0.3030 0.1825 -0.2315 0.086 Uiso 1 1 calc R . . . .
C12 C 0.2669(4) 0.3576(4) -0.0978(3) 0.0686(8) Uani 1 1 d . . . . .
H12 H 0.3515 0.4494 -0.0919 0.082 Uiso 1 1 calc R . . . .
C13 C 0.1709(4) 0.3814(4) -0.0236(3) 0.0615(7) Uani 1 1 d . . . . .
H13 H 0.1908 0.4894 0.0321 0.074 Uiso 1 1 calc R . . . .
C14 C 0.1937(3) 0.6760(3) 0.3516(2) 0.0536(6) Uani 1 1 d . . . . .
C15 C 0.2901(4) 0.7626(4) 0.3011(3) 0.0721(8) Uani 1 1 d . . . . .
H15 H 0.3270 0.7067 0.2394 0.087 Uiso 1 1 calc R . . . .
C16 C 0.3321(5) 0.9322(5) 0.3418(3) 0.0835(10) Uani 1 1 d . . . . .
H16 H 0.3975 0.9899 0.3070 0.100 Uiso 1 1 calc R . . . .
C17 C 0.2793(4) 1.0189(4) 0.4333(3) 0.0725(8) Uani 1 1 d . . . . .
C18 C 0.1826(4) 0.9290(4) 0.4814(3) 0.0764(9) Uani 1 1 d . . . . .
H18 H 0.1445 0.9846 0.5422 0.092 Uiso 1 1 calc R . . . .
C19 C 0.1397(4) 0.7596(4) 0.4433(3) 0.0680(8) Uani 1 1 d . . . . .
H19 H 0.0752 0.7023 0.4788 0.082 Uiso 1 1 calc R . . . .
C20 C 0.3251(5) 1.2053(5) 0.4774(4) 0.1042(13) Uani 1 1 d . . . . .
H20A H 0.2463 1.2348 0.5114 0.156 Uiso 1 1 calc GR . . . .
H20B H 0.3290 1.2337 0.4075 0.156 Uiso 1 1 calc GR . . . .
H20C H 0.4289 1.2656 0.5415 0.156 Uiso 1 1 calc GR . . . .


_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 1.4379(19) . ?
S1 O2 1.4282(19) . ?
S1 C6 1.744(3) . ?
S1 C14 1.765(3) . ?
N1 C1 1.378(3) . ?
N1 C5 1.386(3) . ?
N1 C6 1.391(3) . ?
N2 C5 1.334(3) . ?
N2 C7 1.347(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.350(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.394(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.348(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.408(4) . ?
C6 C7 1.393(3) . ?
C7 C8 1.482(3) . ?
C8 C9 1.387(4) . ?
C8 C13 1.387(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.387(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.375(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(4) . ?
C14 C19 1.380(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.376(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(5) . ?
C17 C18 1.368(5) . ?
C17 C20 1.513(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(4) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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 C6 106.97(12) . . ?
O1 S1 C14 107.23(12) . . ?
O2 S1 O1 119.34(12) . . ?
O2 S1 C6 106.78(12) . . ?
O2 S1 C14 108.43(13) . . ?
C6 S1 C14 107.58(12) . . ?
C1 N1 C5 121.2(2) . . ?
C1 N1 C6 133.1(3) . . ?
C5 N1 C6 105.7(2) . . ?
C5 N2 C7 106.3(2) . . ?
N1 C1 H1 120.6 . . ?
C2 C1 N1 118.7(3) . . ?
C2 C1 H1 120.6 . . ?
C1 C2 H2 119.2 . . ?
C1 C2 C3 121.5(3) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 118.8(3) . . ?
N2 C5 N1 111.5(2) . . ?
N2 C5 C4 129.7(3) . . ?
N1 C6 S1 121.45(18) . . ?
N1 C6 C7 105.8(2) . . ?
C7 C6 S1 132.3(2) . . ?
N2 C7 C6 110.6(2) . . ?
N2 C7 C8 118.8(2) . . ?
C6 C7 C8 130.5(2) . . ?
C9 C8 C7 118.9(2) . . ?
C9 C8 C13 118.9(3) . . ?
C13 C8 C7 122.0(3) . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.3(3) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C8 C13 H13 119.7 . . ?
C12 C13 C8 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C15 C14 S1 120.2(2) . . ?
C15 C14 C19 119.8(3) . . ?
C19 C14 S1 120.0(2) . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.9(3) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.3 . . ?
C15 C16 C17 121.5(3) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 C20 121.4(3) . . ?
C18 C17 C16 117.3(3) . . ?
C18 C17 C20 121.3(3) . . ?
C17 C18 H18 118.8 . . ?
C17 C18 C19 122.5(3) . . ?
C19 C18 H18 118.8 . . ?
C14 C19 H19 120.5 . . ?
C18 C19 C14 119.0(3) . . ?
C18 C19 H19 120.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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 C6 C7 N2 171.5(2) . . . . ?
S1 C6 C7 C8 -8.8(5) . . . . ?
S1 C14 C15 C16 179.6(3) . . . . ?
S1 C14 C19 C18 -179.1(2) . . . . ?
O1 S1 C6 N1 35.0(2) . . . . ?
O1 S1 C6 C7 -136.2(3) . . . . ?
O1 S1 C14 C15 157.2(2) . . . . ?
O1 S1 C14 C19 -23.1(3) . . . . ?
O2 S1 C6 N1 163.8(2) . . . . ?
O2 S1 C6 C7 -7.3(3) . . . . ?
O2 S1 C14 C15 27.1(3) . . . . ?
O2 S1 C14 C19 -153.2(2) . . . . ?
N1 C1 C2 C3 0.5(5) . . . . ?
N1 C6 C7 N2 -0.6(3) . . . . ?
N1 C6 C7 C8 179.1(2) . . . . ?
N2 C7 C8 C9 -48.3(4) . . . . ?
N2 C7 C8 C13 126.7(3) . . . . ?
C1 N1 C5 N2 -179.8(3) . . . . ?
C1 N1 C5 C4 0.9(4) . . . . ?
C1 N1 C6 S1 7.3(4) . . . . ?
C1 N1 C6 C7 -179.5(3) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 N1 -0.3(4) . . . . ?
C3 C4 C5 N2 -179.5(3) . . . . ?
C5 N1 C1 C2 -1.1(4) . . . . ?
C5 N1 C6 S1 -173.30(19) . . . . ?
C5 N1 C6 C7 -0.1(3) . . . . ?
C5 N2 C7 C6 1.1(3) . . . . ?
C5 N2 C7 C8 -178.6(2) . . . . ?
C6 S1 C14 C15 -88.1(3) . . . . ?
C6 S1 C14 C19 91.6(2) . . . . ?
C6 N1 C1 C2 178.2(3) . . . . ?
C6 N1 C5 N2 0.8(3) . . . . ?
C6 N1 C5 C4 -178.5(3) . . . . ?
C6 C7 C8 C9 132.0(3) . . . . ?
C6 C7 C8 C13 -53.0(4) . . . . ?
C7 N2 C5 N1 -1.2(3) . . . . ?
C7 N2 C5 C4 178.0(3) . . . . ?
C7 C8 C9 C10 176.7(3) . . . . ?
C7 C8 C13 C12 -175.8(3) . . . . ?
C8 C9 C10 C11 -1.7(5) . . . . ?
C9 C8 C13 C12 -0.8(4) . . . . ?
C9 C10 C11 C12 1.1(5) . . . . ?
C10 C11 C12 C13 -0.3(5) . . . . ?
C11 C12 C13 C8 0.2(5) . . . . ?
C13 C8 C9 C10 1.6(4) . . . . ?
C14 S1 C6 N1 -79.9(2) . . . . ?
C14 S1 C6 C7 108.9(3) . . . . ?
C14 C15 C16 C17 0.0(6) . . . . ?
C15 C14 C19 C18 0.7(5) . . . . ?
C15 C16 C17 C18 -0.4(5) . . . . ?
C15 C16 C17 C20 -179.7(3) . . . . ?
C16 C17 C18 C19 0.9(5) . . . . ?
C17 C18 C19 C14 -1.0(5) . . . . ?
C19 C14 C15 C16 -0.2(5) . . . . ?
C20 C17 C18 C19 -179.7(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 1.365
_oxdiff_exptl_absorpt_empirical_full_min 0.777
####################################################################### 
# 
# 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_202007108
_database_code_depnum_ccdc_archive 'CCDC 2046840'
loop_
_audit_author_name
_audit_author_address
'Han LiLi'
;Zhengzhou University
China
;
_audit_update_record             
;
2020-11-27 deposited with the CCDC.	2021-04-02 downloaded from the CCDC.
;
_audit_creation_date             2020-07-23
_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         'C20 H15 F N2 O2 S'
_chemical_formula_sum            'C20 H15 F N2 O2 S'
_chemical_formula_weight         366.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H15N2O4S1F1
_chemical_oxdiff_usercomment     r
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'
F F 0.0727 0.0534 '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                   13.7672(3)
_cell_length_b                   12.5717(3)
_cell_length_c                   10.2914(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.758(2)
_cell_angle_gamma                90
_cell_volume                     1749.90(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2597
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8380
_cell_measurement_theta_min      4.7990
_shelx_estimated_absorpt_T_max   0.806
_shelx_estimated_absorpt_T_min   0.693
_exptl_absorpt_coefficient_mu    1.881
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6568
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.063
_diffrn_reflns_theta_max         67.063
_diffrn_reflns_theta_min         4.802
_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 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    -71.00 -37.00   1.00    1.00    --  -33.50 178.00   0.00   34
  2  ω    -82.00 -56.00   1.00    1.00    --  -33.50 -37.00 -30.00   26
  3  ω    -73.00 -34.00   1.00    1.00    --  -33.50 178.00 150.00   39
  4  ω    -51.00 -13.00   1.00    1.00    --  -33.50 -37.00 -30.00   38
  5  ω     32.00  57.00   1.00    1.00    --   36.47 -77.00 -30.00   25
  6  ω     70.00  96.00   1.00    1.00    --   36.47 178.00 -30.00   26
  7  ω     -8.00  18.00   1.00    1.00    --   36.47 -77.00 -30.00   26
  8  ω     -4.00  74.00   1.00    1.00    --   36.47 -99.00 150.00   78
  9  ω     79.00 105.00   1.00    1.00    --   36.47 178.00-150.00   26
 10  ω    -28.00  59.00   1.00    1.00    --   36.47 -37.00-120.00   87
 11  ω    101.00 167.00   1.00    4.00    --  108.00  30.00 -30.00   66
 12  ω     40.00 128.00   1.00    4.00    --  108.00 -61.00 150.00   88
 13  ω     41.00 121.00   1.00    4.00    --  108.00 -61.00   0.00   80
 14  ω     79.00 105.00   1.00    4.00    --  108.00  77.00 -69.00   26
 15  ω     88.00 128.00   1.00    4.00    --  108.00 -45.00 150.00   40
 16  ω    133.00 169.00   1.00    4.00    --  108.00  77.00 -69.00   36
 17  ω     41.00 100.00   1.00    4.00    --  108.00 -94.00   0.00   59
 18  ω     46.00 105.00   1.00    4.00    --  108.00 -45.00 -90.00   59
 19  ω     79.00 133.00   1.00    4.00    --  108.00 -30.00  90.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0711819000
_diffrn_orient_matrix_UB_12      0.0696396000
_diffrn_orient_matrix_UB_13      -0.0979816000
_diffrn_orient_matrix_UB_21      -0.0124124000
_diffrn_orient_matrix_UB_22      0.0754692000
_diffrn_orient_matrix_UB_23      0.1137049000
_diffrn_orient_matrix_UB_31      0.0880240000
_diffrn_orient_matrix_UB_32      0.0668766000
_diffrn_orient_matrix_UB_33      -0.0263748000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2623
_reflns_number_total             3126
_reflns_odcompleteness_completeness 99.94
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (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         0.297
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0436
_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)+(0.0655P)²+0.2648P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1252
_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. Uiso/Uaniso restraints and constraints
Uanis(C15) = Uanis(C15A)
Uanis(C16) = Uanis(C16A)
Uanis(C19) = Uanis(C19A)
Uanis(C18) = Uanis(C18A)
3. Others
 Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=
 Sof(H19A)=1-FVAR(1)
 Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C15A(H15A), C16A(H16A), C18A(H18A), C19A(H19A), C15(H15), C16(H16), C18(H18),
 C19(H19)
4.b Fitted hexagon refined as free rotating group:
 C14(C15A,C16A,C17,C18A,C19A)
4.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_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
S1 S 0.72662(4) 0.39611(4) 1.04068(5) 0.04172(18) Uani 1 1 d . . . . .
F1 F 0.88049(12) -0.00251(10) 0.96341(16) 0.0635(4) Uani 1 1 d . . . . .
O1 O 0.70702(13) 0.29608(14) 1.09774(18) 0.0580(4) Uani 1 1 d . . . . .
O2 O 0.75030(13) 0.48637(14) 1.12485(16) 0.0560(4) Uani 1 1 d . . . . .
N1 N 0.85661(12) 0.27722(13) 0.92116(16) 0.0354(4) Uani 1 1 d . . . . .
N2 N 0.91222(13) 0.39906(13) 0.79200(18) 0.0413(4) Uani 1 1 d . . . . .
C1 C 0.84601(16) 0.17661(17) 0.9698(2) 0.0422(5) Uani 1 1 d . . . . .
H1 H 0.8089 0.1645 1.0352 0.051 Uiso 1 1 calc R . . . .
C2 C 0.89172(17) 0.09676(16) 0.9186(2) 0.0455(5) Uani 1 1 d . . . . .
C3 C 0.94980(17) 0.10999(17) 0.8218(2) 0.0487(5) Uani 1 1 d . . . . .
H3 H 0.9803 0.0521 0.7900 0.058 Uiso 1 1 calc R . . . .
C4 C 0.96038(16) 0.20978(18) 0.7757(2) 0.0464(5) Uani 1 1 d . . . . .
H4 H 0.9991 0.2212 0.7120 0.056 Uiso 1 1 calc R . . . .
C5 C 0.91263(15) 0.29562(16) 0.8246(2) 0.0384(4) Uani 1 1 d . . . . .
C6 C 0.82105(15) 0.37608(15) 0.9510(2) 0.0375(4) Uani 1 1 d . . . . .
C7 C 0.85582(14) 0.44758(16) 0.86817(19) 0.0368(4) Uani 1 1 d . . . . .
C8 C 0.83223(15) 0.56237(16) 0.8507(2) 0.0403(4) Uani 1 1 d . . . . .
C9 C 0.86346(19) 0.63618(18) 0.9497(2) 0.0504(5) Uani 1 1 d . . . . .
H9 H 0.8985 0.6141 1.0314 0.060 Uiso 1 1 calc R . . . .
C10 C 0.8422(2) 0.7432(2) 0.9263(3) 0.0635(7) Uani 1 1 d . . . . .
H10 H 0.8652 0.7929 0.9918 0.076 Uiso 1 1 calc R . . . .
C11 C 0.7880(2) 0.7763(2) 0.8086(3) 0.0649(7) Uani 1 1 d . . . . .
H11 H 0.7730 0.8480 0.7945 0.078 Uiso 1 1 calc R . . . .
C12 C 0.7558(2) 0.7033(2) 0.7114(3) 0.0677(7) Uani 1 1 d . . . . .
H12 H 0.7178 0.7256 0.6317 0.081 Uiso 1 1 calc R . . . .
C13 C 0.7792(2) 0.59652(19) 0.7304(2) 0.0541(6) Uani 1 1 d . . . . .
H13 H 0.7593 0.5480 0.6625 0.065 Uiso 1 1 calc R . . . .
C14 C 0.62486(14) 0.43023(18) 0.91657(19) 0.0453(5) Uani 1 1 d . . . . .
C15A C 0.5702(6) 0.35079(15) 0.8424(9) 0.0759(18) Uani 0.35(2) 1 d G . P A 2
H15A H 0.5857 0.2797 0.8605 0.091 Uiso 0.35(2) 1 calc R . P A 2
C16A C 0.4923(6) 0.3777(2) 0.7412(9) 0.090(2) Uani 0.35(2) 1 d G . P A 2
H16A H 0.4557 0.3245 0.6915 0.108 Uiso 0.35(2) 1 calc R . P A 2
C17 C 0.46907(17) 0.4839(3) 0.7141(2) 0.0698(8) Uani 1 1 d G . . A .
C18A C 0.5237(6) 0.56338(19) 0.7883(8) 0.0595(14) Uani 0.35(2) 1 d G . P A 2
H18A H 0.5082 0.6345 0.7702 0.071 Uiso 0.35(2) 1 calc R . P A 2
C19A C 0.6016(6) 0.53652(16) 0.8895(8) 0.0493(13) Uani 0.35(2) 1 d G . P A 2
H19A H 0.6382 0.5897 0.9392 0.059 Uiso 0.35(2) 1 calc R . P A 2
C15 C 0.5905(7) 0.3562(4) 0.8175(9) 0.0759(18) Uani 0.65(2) 1 d . . P A 1
H15 H 0.6185 0.2888 0.8187 0.091 Uiso 0.65(2) 1 calc R . P A 1
C16 C 0.5142(8) 0.3859(5) 0.7181(9) 0.090(2) Uani 0.65(2) 1 d . . P A 1
H16 H 0.4920 0.3377 0.6505 0.108 Uiso 0.65(2) 1 calc R . P A 1
C18 C 0.5070(6) 0.5548(5) 0.8134(9) 0.0595(14) Uani 0.65(2) 1 d . . P A 1
H18 H 0.4790 0.6222 0.8125 0.071 Uiso 0.65(2) 1 calc R . P A 1
C19 C 0.5844(6) 0.5296(4) 0.9135(8) 0.0493(13) Uani 0.65(2) 1 d . . P A 1
H19 H 0.6089 0.5794 0.9782 0.059 Uiso 0.65(2) 1 calc R . P A 1
C20 C 0.3852(3) 0.5131(3) 0.6036(4) 0.1005(13) Uani 1 1 d . . . . .
H20A H 0.4043 0.4996 0.5200 0.151 Uiso 1 1 calc GR . . A .
H20B H 0.3697 0.5871 0.6099 0.151 Uiso 1 1 calc GR . . . .
H20C H 0.3281 0.4711 0.6104 0.151 Uiso 1 1 calc GR . . . .


_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 1.4348(17) . ?
S1 O2 1.4278(17) . ?
S1 C6 1.747(2) . ?
S1 C14 1.7636(17) . ?
F1 C2 1.349(2) . ?
N1 C1 1.378(3) . ?
N1 C5 1.386(3) . ?
N1 C6 1.391(2) . ?
N2 C5 1.343(3) . ?
N2 C7 1.348(3) . ?
C1 C2 1.344(3) . ?
C2 C3 1.398(3) . ?
C3 C4 1.359(3) . ?
C4 C5 1.405(3) . ?
C6 C7 1.384(3) . ?
C7 C8 1.483(3) . ?
C8 C9 1.386(3) . ?
C8 C13 1.383(3) . ?
C9 C10 1.388(3) . ?
C10 C11 1.364(4) . ?
C11 C12 1.369(4) . ?
C12 C13 1.386(3) . ?
C14 C15A 1.3900 . ?
C14 C19A 1.3900 . ?
C14 C15 1.396(6) . ?
C14 C19 1.365(5) . ?
C15A C16A 1.3900 . ?
C16A C17 1.3900 . ?
C17 C18A 1.3900 . ?
C17 C16 1.377(7) . ?
C17 C18 1.383(7) . ?
C17 C20 1.507(4) . ?
C18A C19A 1.3900 . ?
C15 C16 1.375(7) . ?
C18 C19 1.374(6) . ?

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 C6 107.77(9) . . ?
O1 S1 C14 108.96(11) . . ?
O2 S1 O1 119.17(11) . . ?
O2 S1 C6 109.08(10) . . ?
O2 S1 C14 107.86(11) . . ?
C6 S1 C14 102.78(10) . . ?
C1 N1 C5 121.63(17) . . ?
C1 N1 C6 132.40(18) . . ?
C5 N1 C6 105.97(16) . . ?
C5 N2 C7 105.60(17) . . ?
C2 C1 N1 117.0(2) . . ?
F1 C2 C3 118.1(2) . . ?
C1 C2 F1 117.7(2) . . ?
C1 C2 C3 124.2(2) . . ?
C4 C3 C2 118.12(19) . . ?
C3 C4 C5 119.8(2) . . ?
N1 C5 C4 119.25(19) . . ?
N2 C5 N1 111.33(18) . . ?
N2 C5 C4 129.4(2) . . ?
N1 C6 S1 124.94(15) . . ?
C7 C6 S1 127.49(15) . . ?
C7 C6 N1 105.52(17) . . ?
N2 C7 C6 111.55(18) . . ?
N2 C7 C8 120.45(18) . . ?
C6 C7 C8 127.84(18) . . ?
C9 C8 C7 122.1(2) . . ?
C13 C8 C7 118.5(2) . . ?
C13 C8 C9 119.3(2) . . ?
C8 C9 C10 119.7(2) . . ?
C11 C10 C9 120.8(2) . . ?
C10 C11 C12 119.5(2) . . ?
C11 C12 C13 120.8(3) . . ?
C8 C13 C12 119.8(2) . . ?
C15A C14 S1 119.90(14) . . ?
C15A C14 C19A 120.0 . . ?
C19A C14 S1 120.05(14) . . ?
C15 C14 S1 118.8(3) . . ?
C19 C14 S1 120.3(2) . . ?
C19 C14 C15 120.8(3) . . ?
C14 C15A C16A 120.0 . . ?
C17 C16A C15A 120.0 . . ?
C16A C17 C20 120.0(3) . . ?
C18A C17 C16A 120.0 . . ?
C18A C17 C20 120.0(3) . . ?
C16 C17 C18 116.7(3) . . ?
C16 C17 C20 121.2(4) . . ?
C18 C17 C20 122.1(3) . . ?
C17 C18A C19A 120.0 . . ?
C18A C19A C14 120.0 . . ?
C16 C15 C14 118.0(4) . . ?
C15 C16 C17 122.9(5) . . ?
C19 C18 C17 122.6(4) . . ?
C14 C19 C18 119.0(4) . . ?

_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 1.179
_oxdiff_exptl_absorpt_empirical_full_min 0.887
####################################################################### 
# 
# 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_202007110
_database_code_depnum_ccdc_archive 'CCDC 2046849'
loop_
_audit_author_name
_audit_author_address
'Han LiLi'
;Zhengzhou University
China
;
_audit_update_record             
;
2020-11-27 deposited with the CCDC.	2021-04-02 downloaded from the CCDC.
;
_audit_creation_date             2020-07-23
_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         'C23 H22 N2 O2 S'
_chemical_formula_sum            'C23 H22 N2 O2 S'
_chemical_formula_weight         390.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H15N2O4S1
_chemical_oxdiff_usercomment     r
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                   17.5438(7)
_cell_length_b                   18.4815(6)
_cell_length_c                   13.4134(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.063(4)
_cell_angle_gamma                90
_cell_volume                     4157.6(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3796
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8540
_cell_measurement_theta_min      4.1840
_shelx_estimated_absorpt_T_max   0.861
_shelx_estimated_absorpt_T_min   0.728
_exptl_absorpt_coefficient_mu    1.541
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17564
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         3.559
_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 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    -56.00 -15.00   1.00    1.50    --  -33.50 -57.00  30.00   41
  2  ω    -51.00 -18.00   1.00    1.50    --  -33.50 -57.00   0.00   33
  3  ω    -25.00  24.00   1.00    1.50    --  -33.50  37.00 150.00   49
  4  ω    -44.00  -5.00   1.00    1.50    --  -33.50 -77.00 -90.00   39
  5  ω    -76.00 -49.00   1.00    1.50    --  -33.50 -77.00 -90.00   27
  6  ω    -81.00 -54.00   1.00    1.50    --  -33.50 -57.00   0.00   27
  7  ω    -87.00 -60.00   1.00    1.50    --  -33.50 -57.00  30.00   27
  8  ω     19.00 104.00   1.00    1.50    --   36.47  57.00 -90.00   85
  9  ω     19.00 105.00   1.00    1.50    --   36.47  57.00  30.00   86
 10  ω     80.00 105.00   1.00    1.50    --   36.47  57.00  90.00   25
 11  ω     25.00  52.00   1.00    1.50    --   36.47  57.00  90.00   27
 12  ω     67.00 100.00   1.00    1.50    --   36.47 178.00 -90.00   33
 13  ω    105.00 131.00   1.00    7.50    --  108.00 111.00 -90.00   26
 14  ω    152.00 178.00   1.00    7.50    --  108.00  45.00   0.00   26
 15  ω     95.00 122.00   1.00    7.50    --  108.00  45.00   0.00   27
 16  ω     40.00 123.00   1.00    7.50    --  108.00 -30.00-150.00   83
 17  ω     83.00 109.00   1.00    7.50    --  108.00 -94.00  60.00   26
 18  ω     72.00 121.00   1.00    7.50    --  108.00 -61.00   0.00   49
 19  ω    102.00 149.00   1.00    7.50    --  108.00 111.00 -60.00   47
 20  ω     41.00 126.00   1.00    7.50    --  108.00 -61.00-150.00   85
 21  ω    153.00 178.00   1.00    7.50    --  108.00 111.00 -90.00   25
 22  ω     91.00 176.00   1.00    7.50    --  108.00  45.00  30.00   85
 23  ω     71.00 153.00   1.00    7.50    --  108.00 -15.00 -30.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0452279000
_diffrn_orient_matrix_UB_12      -0.0210287000
_diffrn_orient_matrix_UB_13      0.1130211000
_diffrn_orient_matrix_UB_21      0.0647483000
_diffrn_orient_matrix_UB_22      0.0564827000
_diffrn_orient_matrix_UB_23      0.0005176000
_diffrn_orient_matrix_UB_31      -0.0469084000
_diffrn_orient_matrix_UB_32      0.0575445000
_diffrn_orient_matrix_UB_33      0.0407763000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5149
_reflns_number_total             7412
_reflns_odcompleteness_completeness 99.90
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (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         0.498
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     536
_refine_ls_number_reflns         7412
_refine_ls_number_restraints     108
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0541
_refine_ls_restrained_S_all      1.037
_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)+(0.0786P)²+1.0512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1675
_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
 C21'-C23' \\sim C21'-C22' \\sim C23'-C22' \\sim C1A-C1B \\sim C1A-C1C \\sim
C1B-C1C
 with sigma of 0.04
 C20'-C17' \\sim C20'-C21' \\sim C20'-C23' \\sim C20'-C22' \\sim C20'-C1A \\sim
C20'-C1B \\sim C20'-C1C
 with sigma of 0.02
 C22-C23 \\sim C22-C21 \\sim C23-C21 \\sim C23A-C22A \\sim C23A-C21A \\sim
C22A-C21A
 with sigma of 0.04
 C20-C17 \\sim C20-C22 \\sim C20-C23 \\sim C20-C21 \\sim C20-C23A \\sim
C20-C22A \\sim C20-C21A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C21') \\sim Ueq, Uanis(C1B) \\sim Ueq, Uanis(C1C) \\sim Ueq, Uanis(C22')
\\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C23') \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C23) = Uanis(C23A)
Uanis(C22) = Uanis(C22A)
Uanis(C21) = Uanis(C21A)
Uanis(C22') = Uanis(C1A)
Uanis(C23') = Uanis(C1B)
Uanis(C21') = Uanis(C1C)
4. Others
 Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(C22A)=Sof(H22D)=Sof(H22E)=
 Sof(H22F)=Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=1-FVAR(1)
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=
 Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=FVAR(1)
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=
 Sof(C1C)=Sof(H1CA)=Sof(H1CB)=Sof(H1CC)=1-FVAR(2)
 Sof(C21')=Sof(H21G)=Sof(H21H)=Sof(H21I)=Sof(C22')=Sof(H22G)=Sof(H22H)=
 Sof(H22I)=Sof(C23')=Sof(H23G)=Sof(H23H)=Sof(H23I)=FVAR(2)
5.a Riding coordinates:
 C1A(H1AA,H1AB,H1AC)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C18(H18), C19(H19), C1'(H1'), C2'(H2'), C3'(H3'),
  C4'(H4'), C9'(H9'), C10'(H10'), C11'(H11'), C12'(H12'), C13'(H13'),
 C15'(H15'), C16'(H16'), C18'(H18'), C19'(H19')
5.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C21A(H21D,H21E,H21F), C22(H22A,H22B,H22C), C22A(H22D,
 H22E,H22F), C23(H23A,H23B,H23C), C23A(H23D,H23E,H23F), C1B(H1BA,H1BB,H1BC),
 C1C(H1CA,H1CB,H1CC), C21'(H21G,H21H,H21I), C22'(H22G,H22H,H22I), C23'(H23G,
 H23H,H23I)
;
_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
S1 S 0.54594(4) 0.20620(4) 0.33258(6) 0.05068(19) Uani 1 1 d . . . . .
O1 O 0.57102(14) 0.17168(12) 0.25175(17) 0.0626(6) Uani 1 1 d . . . . .
O2 O 0.51660(13) 0.27869(11) 0.31711(17) 0.0608(5) Uani 1 1 d . . . . .
N1 N 0.47309(14) 0.07775(13) 0.35335(17) 0.0493(5) Uani 1 1 d . . . . .
N2 N 0.37604(16) 0.10968(16) 0.4234(2) 0.0632(7) Uani 1 1 d . . . . .
C1 C 0.5213(2) 0.02939(17) 0.3213(2) 0.0578(7) Uani 1 1 d . . . . .
H1 H 0.5626 0.0459 0.2967 0.069 Uiso 1 1 calc R . . . .
C2 C 0.5076(2) -0.04212(18) 0.3261(3) 0.0666(9) Uani 1 1 d . . . . .
H2 H 0.5397 -0.0751 0.3046 0.080 Uiso 1 1 calc R . . . .
C3 C 0.4452(3) -0.06754(19) 0.3634(3) 0.0768(11) Uani 1 1 d . . . . .
H3 H 0.4362 -0.1170 0.3660 0.092 Uiso 1 1 calc R . . . .
C4 C 0.3985(2) -0.0205(2) 0.3953(3) 0.0714(10) Uani 1 1 d . . . . .
H4 H 0.3571 -0.0376 0.4190 0.086 Uiso 1 1 calc R . . . .
C5 C 0.41227(19) 0.05420(18) 0.3928(2) 0.0580(8) Uani 1 1 d . . . . .
C6 C 0.47239(17) 0.15281(15) 0.3591(2) 0.0487(6) Uani 1 1 d . . . . .
C7 C 0.41266(17) 0.17054(17) 0.4038(2) 0.0531(7) Uani 1 1 d . . . . .
C8 C 0.38947(17) 0.24205(18) 0.4339(2) 0.0557(7) Uani 1 1 d . . . . .
C9 C 0.3639(2) 0.2976(2) 0.3629(3) 0.0731(9) Uani 1 1 d . . . . .
H9 H 0.3610 0.2903 0.2933 0.088 Uiso 1 1 calc R . . . .
C10 C 0.3424(3) 0.3638(2) 0.3942(4) 0.0926(13) Uani 1 1 d . . . . .
H10 H 0.3254 0.4008 0.3457 0.111 Uiso 1 1 calc R . . . .
C11 C 0.3462(3) 0.3754(3) 0.4965(4) 0.0937(13) Uani 1 1 d . . . . .
H11 H 0.3319 0.4200 0.5176 0.112 Uiso 1 1 calc R . . . .
C12 C 0.3712(3) 0.3204(3) 0.5674(4) 0.0912(13) Uani 1 1 d . . . . .
H12 H 0.3735 0.3280 0.6368 0.109 Uiso 1 1 calc R . . . .
C13 C 0.3929(2) 0.2538(2) 0.5370(3) 0.0745(10) Uani 1 1 d . . . . .
H13 H 0.4098 0.2171 0.5858 0.089 Uiso 1 1 calc R . . . .
C14 C 0.62551(17) 0.20287(15) 0.4485(2) 0.0479(6) Uani 1 1 d . . . . .
C15 C 0.69101(19) 0.16000(17) 0.4548(2) 0.0558(7) Uani 1 1 d . . . . .
H15 H 0.6939 0.1329 0.3976 0.067 Uiso 1 1 calc R . . . .
C16 C 0.75248(19) 0.15764(18) 0.5472(2) 0.0588(8) Uani 1 1 d . . . . .
H16 H 0.7967 0.1287 0.5512 0.071 Uiso 1 1 calc R . . . .
C17 C 0.74988(18) 0.19750(16) 0.6343(2) 0.0521(7) Uani 1 1 d D . . . .
C18 C 0.68268(19) 0.23967(17) 0.6259(2) 0.0558(7) Uani 1 1 d . . . . .
H18 H 0.6794 0.2666 0.6830 0.067 Uiso 1 1 calc R . . . .
C19 C 0.62086(19) 0.24250(16) 0.5345(2) 0.0541(7) Uani 1 1 d . . . . .
H19 H 0.5762 0.2708 0.5305 0.065 Uiso 1 1 calc R . . . .
C20 C 0.8181(2) 0.19413(19) 0.7358(3) 0.0652(8) Uani 1 1 d D . . . .
C21 C 0.8945(3) 0.2140(5) 0.7127(5) 0.101(2) Uani 0.673(4) 1 d D . P A 1
H21A H 0.9032 0.1814 0.6613 0.152 Uiso 0.673(4) 1 calc GR . P A 1
H21B H 0.9382 0.2105 0.7754 0.152 Uiso 0.673(4) 1 calc GR . P A 1
H21C H 0.8908 0.2626 0.6866 0.152 Uiso 0.673(4) 1 calc GR . P A 1
C21A C 0.8499(8) 0.2723(6) 0.7720(11) 0.101(2) Uani 0.327(4) 1 d D . P A 2
H21D H 0.8688 0.2946 0.7190 0.152 Uiso 0.327(4) 1 calc GR . P A 2
H21E H 0.8928 0.2692 0.8357 0.152 Uiso 0.327(4) 1 calc GR . P A 2
H21F H 0.8075 0.3009 0.7833 0.152 Uiso 0.327(4) 1 calc GR . P A 2
C22 C 0.8244(5) 0.1142(4) 0.7726(5) 0.0971(19) Uani 0.673(4) 1 d D . P A 1
H22A H 0.7737 0.0985 0.7784 0.146 Uiso 0.673(4) 1 calc GR . P A 1
H22B H 0.8638 0.1103 0.8393 0.146 Uiso 0.673(4) 1 calc GR . P A 1
H22C H 0.8395 0.0844 0.7229 0.146 Uiso 0.673(4) 1 calc GR . P A 1
C22A C 0.8921(8) 0.1512(8) 0.7330(10) 0.0971(19) Uani 0.327(4) 1 d D . P A 2
H22D H 0.8820 0.1004 0.7372 0.146 Uiso 0.327(4) 1 calc GR . P A 2
H22E H 0.9364 0.1651 0.7911 0.146 Uiso 0.327(4) 1 calc GR . P A 2
H22F H 0.9042 0.1613 0.6691 0.146 Uiso 0.327(4) 1 calc GR . P A 2
C23 C 0.8034(4) 0.2397(5) 0.8222(5) 0.103(2) Uani 0.673(4) 1 d D . P A 1
H23A H 0.7985 0.2896 0.8015 0.154 Uiso 0.673(4) 1 calc GR . P A 1
H23B H 0.8472 0.2342 0.8844 0.154 Uiso 0.673(4) 1 calc GR . P A 1
H23C H 0.7551 0.2241 0.8355 0.154 Uiso 0.673(4) 1 calc GR . P A 1
C23A C 0.7883(8) 0.1639(8) 0.8229(9) 0.103(2) Uani 0.327(4) 1 d D . P A 2
H23D H 0.7480 0.1953 0.8341 0.154 Uiso 0.327(4) 1 calc GR . P A 2
H23E H 0.8318 0.1607 0.8858 0.154 Uiso 0.327(4) 1 calc GR . P A 2
H23F H 0.7661 0.1166 0.8038 0.154 Uiso 0.327(4) 1 calc GR . P A 2
S1' S 0.11263(5) 0.54245(5) 0.34330(6) 0.0658(3) Uani 1 1 d . . . . .
O1' O 0.10395(17) 0.60452(15) 0.4045(2) 0.0857(8) Uani 1 1 d . . . . .
O2' O 0.05450(14) 0.5304(2) 0.24560(19) 0.0990(11) Uani 1 1 d . . . . .
N1' N 0.27308(14) 0.56120(14) 0.40518(18) 0.0518(6) Uani 1 1 d . . . . .
N2' N 0.31493(14) 0.53696(14) 0.26608(18) 0.0513(6) Uani 1 1 d . . . . .
C1' C 0.2824(2) 0.5784(2) 0.5075(2) 0.0664(9) Uani 1 1 d . . . . .
H1' H 0.2382 0.5837 0.5317 0.080 Uiso 1 1 calc R . . . .
C1A C 0.145(2) 0.2096(14) 0.561(3) 0.161(4) Uani 0.184(7) 1 d D U P B 2
H1AA H 0.1031 0.1890 0.5044 0.241 Uiso 0.184(7) 1 d R . P B 2
H1AB H 0.1634 0.1740 0.6144 0.241 Uiso 0.184(7) 1 d R . P B 2
H1AC H 0.1878 0.2248 0.5353 0.241 Uiso 0.184(7) 1 d R . P B 2
C1B C 0.1749(17) 0.2910(17) 0.7120(17) 0.147(3) Uani 0.184(7) 1 d D U P B 2
H1BA H 0.2262 0.2988 0.7020 0.220 Uiso 0.184(7) 1 calc GR . P B 2
H1BB H 0.1778 0.2508 0.7583 0.220 Uiso 0.184(7) 1 calc GR . P B 2
H1BC H 0.1591 0.3336 0.7418 0.220 Uiso 0.184(7) 1 calc GR . P B 2
C1C C 0.0335(12) 0.2621(19) 0.621(3) 0.143(3) Uani 0.184(7) 1 d D U P B 2
H1CA H 0.0265 0.2953 0.6731 0.214 Uiso 0.184(7) 1 calc GR . P B 2
H1CB H 0.0307 0.2133 0.6448 0.214 Uiso 0.184(7) 1 calc GR . P B 2
H1CC H -0.0077 0.2697 0.5570 0.214 Uiso 0.184(7) 1 calc GR . P B 2
C2' C 0.3567(2) 0.5873(2) 0.5723(3) 0.0711(9) Uani 1 1 d . . . . .
H2' H 0.3633 0.5985 0.6420 0.085 Uiso 1 1 calc R . . . .
C3' C 0.4241(2) 0.58012(19) 0.5371(3) 0.0672(9) Uani 1 1 d . . . . .
H3' H 0.4748 0.5860 0.5834 0.081 Uiso 1 1 calc R . . . .
C4' C 0.41519(19) 0.56457(18) 0.4358(2) 0.0596(8) Uani 1 1 d . . . . .
H4' H 0.4596 0.5606 0.4117 0.071 Uiso 1 1 calc R . . . .
C5' C 0.33785(17) 0.55441(16) 0.3669(2) 0.0506(7) Uani 1 1 d . . . . .
C6' C 0.20579(17) 0.54708(18) 0.3214(2) 0.0536(7) Uani 1 1 d . . . . .
C7' C 0.23472(17) 0.53168(16) 0.2372(2) 0.0488(6) Uani 1 1 d . . . . .
C8' C 0.19327(16) 0.51241(17) 0.1272(2) 0.0515(7) Uani 1 1 d . . . . .
C9' C 0.12044(18) 0.54151(19) 0.0702(2) 0.0588(8) Uani 1 1 d . . . . .
H9' H 0.0946 0.5747 0.1013 0.071 Uiso 1 1 calc R . . . .
C10' C 0.08614(19) 0.5212(2) -0.0331(2) 0.0675(9) Uani 1 1 d . . . . .
H10' H 0.0368 0.5399 -0.0703 0.081 Uiso 1 1 calc R . . . .
C11' C 0.1244(2) 0.4738(2) -0.0801(3) 0.0736(10) Uani 1 1 d . . . . .
H11' H 0.1008 0.4600 -0.1489 0.088 Uiso 1 1 calc R . . . .
C12' C 0.1978(2) 0.4467(2) -0.0262(3) 0.0772(10) Uani 1 1 d . . . . .
H12' H 0.2243 0.4154 -0.0590 0.093 Uiso 1 1 calc R . . . .
C13' C 0.2324(2) 0.4657(2) 0.0773(3) 0.0656(8) Uani 1 1 d . . . . .
H13' H 0.2821 0.4472 0.1136 0.079 Uiso 1 1 calc R . . . .
C14' C 0.11742(18) 0.46491(19) 0.4216(2) 0.0557(7) Uani 1 1 d . . . . .
C15' C 0.1039(3) 0.4712(2) 0.5167(3) 0.0881(13) Uani 1 1 d . . . . .
H15' H 0.0960 0.5166 0.5420 0.106 Uiso 1 1 calc R . . . .
C16' C 0.1019(3) 0.4102(2) 0.5746(3) 0.0911(13) Uani 1 1 d . . . . .
H16' H 0.0913 0.4151 0.6382 0.109 Uiso 1 1 calc R . . . .
C17' C 0.1150(2) 0.3425(2) 0.5420(3) 0.0719(9) Uani 1 1 d D . . . .
C18' C 0.1288(3) 0.3379(2) 0.4460(4) 0.1031(16) Uani 1 1 d . . . . .
H18' H 0.1377 0.2927 0.4209 0.124 Uiso 1 1 calc R . . . .
C19' C 0.1299(3) 0.3981(2) 0.3866(3) 0.0913(13) Uani 1 1 d . . . . .
H19' H 0.1391 0.3933 0.3221 0.110 Uiso 1 1 calc R . . . .
C20' C 0.1125(3) 0.2744(2) 0.6049(4) 0.0954(14) Uani 1 1 d D . . . .
C21' C 0.0925(6) 0.2901(4) 0.7060(6) 0.143(3) Uani 0.816(7) 1 d D U P B 1
H21G H 0.1373 0.3128 0.7549 0.214 Uiso 0.816(7) 1 calc GR . P B 1
H21H H 0.0803 0.2456 0.7350 0.214 Uiso 0.816(7) 1 calc GR . P B 1
H21I H 0.0472 0.3218 0.6919 0.214 Uiso 0.816(7) 1 calc GR . P B 1
C22' C 0.0440(5) 0.2246(5) 0.5423(7) 0.161(4) Uani 0.816(7) 1 d D U P B 1
H22G H -0.0056 0.2505 0.5260 0.241 Uiso 0.816(7) 1 calc GR . P B 1
H22H H 0.0409 0.1827 0.5833 0.241 Uiso 0.816(7) 1 calc GR . P B 1
H22I H 0.0542 0.2096 0.4789 0.241 Uiso 0.816(7) 1 calc GR . P B 1
C23' C 0.1901(5) 0.2341(5) 0.6252(8) 0.147(3) Uani 0.816(7) 1 d D U P B 1
H23G H 0.2055 0.2321 0.5623 0.220 Uiso 0.816(7) 1 calc GR . P B 1
H23H H 0.1837 0.1859 0.6481 0.220 Uiso 0.816(7) 1 calc GR . P B 1
H23I H 0.2306 0.2587 0.6783 0.220 Uiso 0.816(7) 1 calc GR . P B 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.434(2) . ?
S1 O2 1.428(2) . ?
S1 C6 1.742(3) . ?
S1 C14 1.760(3) . ?
N1 C1 1.384(4) . ?
N1 C5 1.393(4) . ?
N1 C6 1.390(4) . ?
N2 C5 1.333(4) . ?
N2 C7 1.358(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.348(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.412(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.346(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.404(5) . ?
C6 C7 1.391(4) . ?
C7 C8 1.473(4) . ?
C8 C9 1.382(5) . ?
C8 C13 1.384(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.370(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.372(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.385(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(4) . ?
C14 C19 1.389(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.393(4) . ?
C17 C18 1.390(4) . ?
C17 C20 1.528(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.378(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.506(6) . ?
C20 C21A 1.573(11) . ?
C20 C22 1.551(7) . ?
C20 C22A 1.530(10) . ?
C20 C23 1.515(6) . ?
C20 C23A 1.520(11) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C21A H21D 0.9600 . ?
C21A H21E 0.9600 . ?
C21A H21F 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22A H22D 0.9600 . ?
C22A H22E 0.9600 . ?
C22A H22F 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C23A H23D 0.9600 . ?
C23A H23E 0.9600 . ?
C23A H23F 0.9600 . ?
S1' O1' 1.445(3) . ?
S1' O2' 1.422(3) . ?
S1' C6' 1.745(3) . ?
S1' C14' 1.764(3) . ?
N1' C1' 1.371(4) . ?
N1' C5' 1.383(4) . ?
N1' C6' 1.395(4) . ?
N2' C5' 1.333(4) . ?
N2' C7' 1.349(4) . ?
C1' H1' 0.9300 . ?
C1' C2' 1.348(5) . ?
C1A H1AA 0.9599 . ?
C1A H1AB 0.9599 . ?
C1A H1AC 0.9600 . ?
C1A C20' 1.517(14) . ?
C1B H1BA 0.9600 . ?
C1B H1BB 0.9600 . ?
C1B H1BC 0.9600 . ?
C1B C20' 1.560(14) . ?
C1C H1CA 0.9600 . ?
C1C H1CB 0.9600 . ?
C1C H1CC 0.9600 . ?
C1C C20' 1.485(14) . ?
C2' H2' 0.9300 . ?
C2' C3' 1.403(5) . ?
C3' H3' 0.9300 . ?
C3' C4' 1.353(5) . ?
C4' H4' 0.9300 . ?
C4' C5' 1.412(4) . ?
C6' C7' 1.398(4) . ?
C7' C8' 1.484(4) . ?
C8' C9' 1.390(4) . ?
C8' C13' 1.390(5) . ?
C9' H9' 0.9300 . ?
C9' C10' 1.391(4) . ?
C10' H10' 0.9300 . ?
C10' C11' 1.365(5) . ?
C11' H11' 0.9300 . ?
C11' C12' 1.373(5) . ?
C12' H12' 0.9300 . ?
C12' C13' 1.388(5) . ?
C13' H13' 0.9300 . ?
C14' C15' 1.370(5) . ?
C14' C19' 1.360(5) . ?
C15' H15' 0.9300 . ?
C15' C16' 1.376(5) . ?
C16' H16' 0.9300 . ?
C16' C17' 1.365(6) . ?
C17' C18' 1.382(5) . ?
C17' C20' 1.522(5) . ?
C18' H18' 0.9300 . ?
C18' C19' 1.372(6) . ?
C19' H19' 0.9300 . ?
C20' C21' 1.526(7) . ?
C20' C22' 1.551(8) . ?
C20' C23' 1.504(7) . ?
C21' H21G 0.9600 . ?
C21' H21H 0.9600 . ?
C21' H21I 0.9600 . ?
C22' H22G 0.9600 . ?
C22' H22H 0.9600 . ?
C22' H22I 0.9600 . ?
C23' H23G 0.9600 . ?
C23' H23H 0.9600 . ?
C23' H23I 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 C6 108.21(13) . . ?
O1 S1 C14 108.23(14) . . ?
O2 S1 O1 119.01(13) . . ?
O2 S1 C6 107.70(14) . . ?
O2 S1 C14 108.64(13) . . ?
C6 S1 C14 104.05(13) . . ?
C1 N1 C5 121.6(3) . . ?
C1 N1 C6 132.7(2) . . ?
C6 N1 C5 105.7(2) . . ?
C5 N2 C7 106.4(3) . . ?
N1 C1 H1 120.5 . . ?
C2 C1 N1 118.9(3) . . ?
C2 C1 H1 120.5 . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.8(3) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 118.2(3) . . ?
N2 C5 N1 111.4(3) . . ?
N2 C5 C4 130.4(3) . . ?
N1 C6 S1 122.3(2) . . ?
N1 C6 C7 106.2(2) . . ?
C7 C6 S1 130.7(2) . . ?
N2 C7 C6 110.3(3) . . ?
N2 C7 C8 120.4(3) . . ?
C6 C7 C8 129.2(3) . . ?
C9 C8 C7 122.6(3) . . ?
C9 C8 C13 118.8(3) . . ?
C13 C8 C7 118.7(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.7(4) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.3(4) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.4(4) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.9(4) . . ?
C13 C12 H12 119.6 . . ?
C8 C13 C12 119.9(4) . . ?
C8 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 S1 120.3(2) . . ?
C15 C14 C19 120.2(3) . . ?
C19 C14 S1 119.4(2) . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.3(3) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 119.2 . . ?
C15 C16 C17 121.7(3) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 C20 121.0(3) . . ?
C18 C17 C16 117.6(3) . . ?
C18 C17 C20 121.3(3) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 C17 121.4(3) . . ?
C19 C18 H18 119.3 . . ?
C14 C19 H19 120.1 . . ?
C18 C19 C14 119.7(3) . . ?
C18 C19 H19 120.1 . . ?
C17 C20 C21A 110.6(5) . . ?
C17 C20 C22 106.6(4) . . ?
C17 C20 C22A 116.6(6) . . ?
C21 C20 C17 108.6(3) . . ?
C21 C20 C22 108.2(5) . . ?
C21 C20 C23 112.6(5) . . ?
C22A C20 C21A 104.9(8) . . ?
C23 C20 C17 113.2(4) . . ?
C23 C20 C22 107.3(5) . . ?
C23A C20 C17 110.0(6) . . ?
C23A C20 C21A 105.7(8) . . ?
C23A C20 C22A 108.3(8) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C21A H21D 109.5 . . ?
C20 C21A H21E 109.5 . . ?
C20 C21A H21F 109.5 . . ?
H21D C21A H21E 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C22A H22D 109.5 . . ?
C20 C22A H22E 109.5 . . ?
C20 C22A H22F 109.5 . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C23A H23D 109.5 . . ?
C20 C23A H23E 109.5 . . ?
C20 C23A H23F 109.5 . . ?
H23D C23A H23E 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
O1' S1' C6' 108.47(16) . . ?
O1' S1' C14' 107.54(15) . . ?
O2' S1' O1' 118.8(2) . . ?
O2' S1' C6' 107.85(15) . . ?
O2' S1' C14' 108.50(18) . . ?
C6' S1' C14' 104.86(15) . . ?
C1' N1' C5' 121.5(3) . . ?
C1' N1' C6' 132.4(3) . . ?
C5' N1' C6' 106.1(2) . . ?
C5' N2' C7' 106.7(2) . . ?
N1' C1' H1' 120.5 . . ?
C2' C1' N1' 118.9(3) . . ?
C2' C1' H1' 120.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
C20' C1A H1AA 109.8 . . ?
C20' C1A H1AB 109.4 . . ?
C20' C1A H1AC 109.2 . . ?
H1BA C1B H1BB 109.5 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 109.5 . . ?
C20' C1B H1BA 109.5 . . ?
C20' C1B H1BB 109.5 . . ?
C20' C1B H1BC 109.5 . . ?
H1CA C1C H1CB 109.5 . . ?
H1CA C1C H1CC 109.5 . . ?
H1CB C1C H1CC 109.5 . . ?
C20' C1C H1CA 109.5 . . ?
C20' C1C H1CB 109.5 . . ?
C20' C1C H1CC 109.5 . . ?
C1' C2' H2' 119.3 . . ?
C1' C2' C3' 121.5(3) . . ?
C3' C2' H2' 119.3 . . ?
C2' C3' H3' 120.0 . . ?
C4' C3' C2' 119.9(3) . . ?
C4' C3' H3' 120.0 . . ?
C3' C4' H4' 120.3 . . ?
C3' C4' C5' 119.4(3) . . ?
C5' C4' H4' 120.3 . . ?
N1' C5' C4' 118.8(3) . . ?
N2' C5' N1' 111.3(3) . . ?
N2' C5' C4' 129.9(3) . . ?
N1' C6' S1' 119.1(2) . . ?
N1' C6' C7' 105.5(2) . . ?
C7' C6' S1' 134.9(2) . . ?
N2' C7' C6' 110.4(2) . . ?
N2' C7' C8' 118.0(2) . . ?
C6' C7' C8' 131.6(3) . . ?
C9' C8' C7' 123.8(3) . . ?
C13' C8' C7' 117.4(3) . . ?
C13' C8' C9' 118.6(3) . . ?
C8' C9' H9' 119.9 . . ?
C8' C9' C10' 120.2(3) . . ?
C10' C9' H9' 119.9 . . ?
C9' C10' H10' 119.8 . . ?
C11' C10' C9' 120.4(3) . . ?
C11' C10' H10' 119.8 . . ?
C10' C11' H11' 119.9 . . ?
C10' C11' C12' 120.2(3) . . ?
C12' C11' H11' 119.9 . . ?
C11' C12' H12' 119.9 . . ?
C11' C12' C13' 120.1(4) . . ?
C13' C12' H12' 119.9 . . ?
C8' C13' H13' 119.8 . . ?
C12' C13' C8' 120.4(3) . . ?
C12' C13' H13' 119.8 . . ?
C15' C14' S1' 119.6(3) . . ?
C19' C14' S1' 121.1(3) . . ?
C19' C14' C15' 119.2(3) . . ?
C14' C15' H15' 120.1 . . ?
C14' C15' C16' 119.7(4) . . ?
C16' C15' H15' 120.1 . . ?
C15' C16' H16' 118.8 . . ?
C17' C16' C15' 122.4(4) . . ?
C17' C16' H16' 118.8 . . ?
C16' C17' C18' 116.6(4) . . ?
C16' C17' C20' 123.0(4) . . ?
C18' C17' C20' 120.4(4) . . ?
C17' C18' H18' 119.1 . . ?
C19' C18' C17' 121.7(4) . . ?
C19' C18' H18' 119.1 . . ?
C14' C19' C18' 120.4(3) . . ?
C14' C19' H19' 119.8 . . ?
C18' C19' H19' 119.8 . . ?
C1A C20' C1B 106.0(15) . . ?
C1A C20' C17' 111.3(15) . . ?
C1C C20' C1A 114.0(16) . . ?
C1C C20' C1B 109.0(15) . . ?
C1C C20' C17' 112.9(12) . . ?
C17' C20' C1B 102.8(12) . . ?
C17' C20' C21' 112.7(4) . . ?
C17' C20' C22' 109.6(5) . . ?
C21' C20' C22' 104.4(5) . . ?
C23' C20' C17' 109.8(4) . . ?
C23' C20' C21' 111.4(6) . . ?
C23' C20' C22' 108.7(6) . . ?
C20' C21' H21G 109.5 . . ?
C20' C21' H21H 109.5 . . ?
C20' C21' H21I 109.5 . . ?
H21G C21' H21H 109.5 . . ?
H21G C21' H21I 109.5 . . ?
H21H C21' H21I 109.5 . . ?
C20' C22' H22G 109.5 . . ?
C20' C22' H22H 109.5 . . ?
C20' C22' H22I 109.5 . . ?
H22G C22' H22H 109.5 . . ?
H22G C22' H22I 109.5 . . ?
H22H C22' H22I 109.5 . . ?
C20' C23' H23G 109.5 . . ?
C20' C23' H23H 109.5 . . ?
C20' C23' H23I 109.5 . . ?
H23G C23' H23H 109.5 . . ?
H23G C23' H23I 109.5 . . ?
H23H C23' H23I 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 C6 C7 N2 -171.1(2) . . . . ?
S1 C6 C7 C8 6.1(5) . . . . ?
S1 C14 C15 C16 -179.3(2) . . . . ?
S1 C14 C19 C18 179.5(2) . . . . ?
O1 S1 C6 N1 34.3(3) . . . . ?
O1 S1 C6 C7 -157.3(3) . . . . ?
O1 S1 C14 C15 -11.6(3) . . . . ?
O1 S1 C14 C19 170.0(2) . . . . ?
O2 S1 C6 N1 164.2(2) . . . . ?
O2 S1 C6 C7 -27.4(3) . . . . ?
O2 S1 C14 C15 -142.1(2) . . . . ?
O2 S1 C14 C19 39.5(3) . . . . ?
N1 C1 C2 C3 -0.1(5) . . . . ?
N1 C6 C7 N2 -1.3(3) . . . . ?
N1 C6 C7 C8 175.9(3) . . . . ?
N2 C7 C8 C9 -123.3(4) . . . . ?
N2 C7 C8 C13 56.2(4) . . . . ?
C1 N1 C5 N2 177.0(3) . . . . ?
C1 N1 C5 C4 -2.7(4) . . . . ?
C1 N1 C6 S1 -5.5(4) . . . . ?
C1 N1 C6 C7 -176.4(3) . . . . ?
C1 C2 C3 C4 -0.3(6) . . . . ?
C2 C3 C4 C5 -0.8(6) . . . . ?
C3 C4 C5 N1 2.2(5) . . . . ?
C3 C4 C5 N2 -177.4(4) . . . . ?
C5 N1 C1 C2 1.6(4) . . . . ?
C5 N1 C6 S1 172.2(2) . . . . ?
C5 N1 C6 C7 1.4(3) . . . . ?
C5 N2 C7 C6 0.7(4) . . . . ?
C5 N2 C7 C8 -176.8(3) . . . . ?
C6 S1 C14 C15 103.4(2) . . . . ?
C6 S1 C14 C19 -75.1(3) . . . . ?
C6 N1 C1 C2 179.1(3) . . . . ?
C6 N1 C5 N2 -1.0(3) . . . . ?
C6 N1 C5 C4 179.3(3) . . . . ?
C6 C7 C8 C9 59.8(5) . . . . ?
C6 C7 C8 C13 -120.7(4) . . . . ?
C7 N2 C5 N1 0.2(4) . . . . ?
C7 N2 C5 C4 179.9(3) . . . . ?
C7 C8 C9 C10 179.8(4) . . . . ?
C7 C8 C13 C12 -179.7(3) . . . . ?
C8 C9 C10 C11 -0.1(7) . . . . ?
C9 C8 C13 C12 -0.2(5) . . . . ?
C9 C10 C11 C12 -0.2(7) . . . . ?
C10 C11 C12 C13 0.3(7) . . . . ?
C11 C12 C13 C8 -0.1(7) . . . . ?
C13 C8 C9 C10 0.3(6) . . . . ?
C14 S1 C6 N1 -80.6(3) . . . . ?
C14 S1 C6 C7 87.8(3) . . . . ?
C14 C15 C16 C17 0.1(5) . . . . ?
C15 C14 C19 C18 1.0(4) . . . . ?
C15 C16 C17 C18 0.5(5) . . . . ?
C15 C16 C17 C20 179.8(3) . . . . ?
C16 C17 C18 C19 -0.4(5) . . . . ?
C16 C17 C20 C21 55.6(5) . . . . ?
C16 C17 C20 C21A 125.6(7) . . . . ?
C16 C17 C20 C22 -60.8(4) . . . . ?
C16 C17 C20 C22A 5.9(8) . . . . ?
C16 C17 C20 C23 -178.5(5) . . . . ?
C16 C17 C20 C23A -117.9(7) . . . . ?
C17 C18 C19 C14 -0.4(5) . . . . ?
C18 C17 C20 C21 -125.1(5) . . . . ?
C18 C17 C20 C21A -55.1(7) . . . . ?
C18 C17 C20 C22 118.5(4) . . . . ?
C18 C17 C20 C22A -174.8(7) . . . . ?
C18 C17 C20 C23 0.7(6) . . . . ?
C18 C17 C20 C23A 61.3(7) . . . . ?
C19 C14 C15 C16 -0.9(4) . . . . ?
C20 C17 C18 C19 -179.7(3) . . . . ?
S1' C6' C7' N2' -172.8(3) . . . . ?
S1' C6' C7' C8' 7.9(6) . . . . ?
S1' C14' C15' C16' 175.4(4) . . . . ?
S1' C14' C19' C18' -176.2(4) . . . . ?
O1' S1' C6' N1' 47.9(3) . . . . ?
O1' S1' C6' C7' -141.0(3) . . . . ?
O1' S1' C14' C15' 7.3(4) . . . . ?
O1' S1' C14' C19' -176.5(3) . . . . ?
O2' S1' C6' N1' 177.8(3) . . . . ?
O2' S1' C6' C7' -11.1(4) . . . . ?
O2' S1' C14' C15' -122.4(3) . . . . ?
O2' S1' C14' C19' 53.8(4) . . . . ?
N1' C1' C2' C3' 0.6(6) . . . . ?
N1' C6' C7' N2' -0.9(3) . . . . ?
N1' C6' C7' C8' 179.9(3) . . . . ?
N2' C7' C8' C9' -142.5(3) . . . . ?
N2' C7' C8' C13' 33.6(4) . . . . ?
C1' N1' C5' N2' 179.5(3) . . . . ?
C1' N1' C5' C4' 0.8(4) . . . . ?
C1' N1' C6' S1' -5.5(5) . . . . ?
C1' N1' C6' C7' -179.0(3) . . . . ?
C1' C2' C3' C4' 0.6(6) . . . . ?
C2' C3' C4' C5' -1.2(5) . . . . ?
C3' C4' C5' N1' 0.4(5) . . . . ?
C3' C4' C5' N2' -177.9(3) . . . . ?
C5' N1' C1' C2' -1.4(5) . . . . ?
C5' N1' C6' S1' 174.1(2) . . . . ?
C5' N1' C6' C7' 0.7(3) . . . . ?
C5' N2' C7' C6' 0.8(3) . . . . ?
C5' N2' C7' C8' -179.9(3) . . . . ?
C6' S1' C14' C15' 122.6(3) . . . . ?
C6' S1' C14' C19' -61.2(4) . . . . ?
C6' N1' C1' C2' 178.2(3) . . . . ?
C6' N1' C5' N2' -0.2(3) . . . . ?
C6' N1' C5' C4' -178.9(3) . . . . ?
C6' C7' C8' C9' 36.7(5) . . . . ?
C6' C7' C8' C13' -147.2(3) . . . . ?
C7' N2' C5' N1' -0.3(3) . . . . ?
C7' N2' C5' C4' 178.1(3) . . . . ?
C7' C8' C9' C10' 179.1(3) . . . . ?
C7' C8' C13' C12' -178.7(3) . . . . ?
C8' C9' C10' C11' -1.5(5) . . . . ?
C9' C8' C13' C12' -2.4(5) . . . . ?
C9' C10' C11' C12' -0.9(6) . . . . ?
C10' C11' C12' C13' 1.7(6) . . . . ?
C11' C12' C13' C8' 0.0(6) . . . . ?
C13' C8' C9' C10' 3.1(5) . . . . ?
C14' S1' C6' N1' -66.7(3) . . . . ?
C14' S1' C6' C7' 104.4(3) . . . . ?
C14' C15' C16' C17' 1.6(8) . . . . ?
C15' C14' C19' C18' 0.0(7) . . . . ?
C15' C16' C17' C18' -1.3(7) . . . . ?
C15' C16' C17' C20' -179.6(5) . . . . ?
C16' C17' C18' C19' 0.4(8) . . . . ?
C16' C17' C20' C1A -169.1(16) . . . . ?
C16' C17' C20' C1B -56.0(15) . . . . ?
C16' C17' C20' C1C 61.3(17) . . . . ?
C16' C17' C20' C21' 1.1(7) . . . . ?
C16' C17' C20' C22' 116.9(6) . . . . ?
C16' C17' C20' C23' -123.8(6) . . . . ?
C17' C18' C19' C14' 0.3(8) . . . . ?
C18' C17' C20' C1A 12.7(17) . . . . ?
C18' C17' C20' C1B 125.7(14) . . . . ?
C18' C17' C20' C1C -117.0(17) . . . . ?
C18' C17' C20' C21' -177.1(6) . . . . ?
C18' C17' C20' C22' -61.3(7) . . . . ?
C18' C17' C20' C23' 58.0(7) . . . . ?
C19' C14' C15' C16' -0.9(7) . . . . ?
C20' C17' C18' C19' 178.7(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 1.695
_oxdiff_exptl_absorpt_empirical_full_min 0.819
####################################################################### 
# 
# 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_202007107
_database_code_depnum_ccdc_archive 'CCDC 2046836'
loop_
_audit_author_name
_audit_author_address
'Han LiLi'
;Zhengzhou University
China
;
_audit_update_record             
;
2020-11-27 deposited with the CCDC.	2021-04-02 downloaded from the CCDC.
;
_audit_creation_date             2020-07-23
_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         'C21 H18 N2 O3 S'
_chemical_formula_sum            'C21 H18 N2 O3 S'
_chemical_formula_weight         378.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H15N2O4S1
_chemical_oxdiff_usercomment     r
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                   8.29236(19)
_cell_length_b                   14.5610(4)
_cell_length_c                   15.4305(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.003(2)
_cell_angle_gamma                90
_cell_volume                     1862.87(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2379
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3070
_cell_measurement_theta_min      4.1540
_shelx_estimated_absorpt_T_max   0.845
_shelx_estimated_absorpt_T_min   0.722
_exptl_absorpt_coefficient_mu    1.745
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6802
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         4.175
_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 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    -50.00 -23.00   1.00    1.25    --  -33.50  37.00 -30.00   27
  2  ω     -4.00  26.00   1.00    1.25    --  -33.50  37.00 -30.00   30
  3  ω   -105.00 -63.00   1.00    1.25    --  -33.50 178.00  60.00   42
  4  ω     58.00 102.00   1.00    1.25    --   36.47 178.00 -60.00   44
  5  ω     59.00 110.00   1.00    1.25    --   36.47 178.00   0.00   51
  6  ω     39.00  65.00   1.00    1.25    --   36.47  57.00 -60.00   26
  7  ω    -32.00  57.00   1.00    1.25    --   36.47 -77.00   0.00   89
  8  ω    -32.00  11.00   1.00    1.25    --   36.47 -57.00 120.00   43
  9  ω     59.00 103.00   1.00    1.25    --   36.47 178.00-180.00   44
 10  ω    100.00 128.00   1.00    4.00    --  108.00 -30.00   0.00   28
 11  ω     60.00  96.00   1.00    4.00    --  108.00 -30.00   0.00   36
 12  ω     42.00 122.00   1.00    4.00    --  108.00 -30.00  90.00   80
 13  ω     42.00 127.00   1.00    4.00    --  108.00 -61.00   0.00   85
 14  ω     43.00 111.00   1.00    4.00    --  108.00-111.00  30.00   68
 15  ω     83.00 142.00   1.00    4.00    --  108.00  30.00 -90.00   59
 16  ω    100.00 158.00   1.00    4.00    --  108.00 111.00  90.00   58
 17  ω     38.00 113.00   1.00    4.00    --  108.00 -15.00 -60.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1599830000
_diffrn_orient_matrix_UB_12      -0.0535575000
_diffrn_orient_matrix_UB_13      -0.0039863000
_diffrn_orient_matrix_UB_21      -0.0870983000
_diffrn_orient_matrix_UB_22      -0.0789033000
_diffrn_orient_matrix_UB_23      -0.0480815000
_diffrn_orient_matrix_UB_31      0.0368716000
_diffrn_orient_matrix_UB_32      0.0457567000
_diffrn_orient_matrix_UB_33      -0.0874304000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2660
_reflns_number_total             3322
_reflns_odcompleteness_completeness 99.88
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (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         0.318
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.036
_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)+(0.0669P)²+0.2248P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1319
_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. Uiso/Uaniso restraints and constraints
Uanis(C19) = Uanis(C19A)
Uanis(C18) = Uanis(C18A)
Uanis(C16) = Uanis(C16A)
Uanis(C15) = Uanis(C15A)
3. Others
 Sof(C19A)=Sof(H19A)=Sof(C18A)=Sof(H18A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=
 Sof(H16A)=1-FVAR(1)
 Sof(C16)=Sof(H16)=Sof(C15)=Sof(H15)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C19A(H19A), C18A(H18A), C16(H16), C15(H15), C15A(H15A), C16A(H16A), C18(H18),
 C19(H19)
4.b Fitted hexagon refined as free rotating group:
 C14(C19A,C18A,C17,C16,C15)
4.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_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
S1 S 0.98090(6) 0.40059(4) 0.24267(3) 0.04701(19) Uani 1 1 d . . . . .
O1 O 1.1380(2) 0.43622(13) 0.26416(11) 0.0611(5) Uani 1 1 d . . . . .
O2 O 0.9632(2) 0.30533(12) 0.22170(11) 0.0579(4) Uani 1 1 d . . . . .
O3 O 1.1116(3) 0.68878(13) 0.47331(12) 0.0709(5) Uani 1 1 d . . . . .
N1 N 0.8732(2) 0.50366(13) 0.37923(11) 0.0465(4) Uani 1 1 d . . . . .
N2 N 0.6297(2) 0.44373(15) 0.40599(12) 0.0521(5) Uani 1 1 d . . . . .
C1 C 1.0025(3) 0.56286(17) 0.39138(14) 0.0522(6) Uani 1 1 d . . . . .
H1 H 1.0946 0.5574 0.3582 0.063 Uiso 1 1 calc R . . . .
C2 C 0.9910(3) 0.62902(18) 0.45298(16) 0.0586(6) Uani 1 1 d . . . . .
C3 C 0.8499(4) 0.63707(19) 0.50244(17) 0.0645(7) Uani 1 1 d . . . . .
H3 H 0.8445 0.6821 0.5450 0.077 Uiso 1 1 calc R . . . .
C4 C 0.7228(4) 0.58070(19) 0.48902(16) 0.0621(7) Uani 1 1 d . . . . .
H4 H 0.6295 0.5876 0.5209 0.075 Uiso 1 1 calc R . . . .
C5 C 0.7336(3) 0.51101(17) 0.42582(15) 0.0508(6) Uani 1 1 d . . . . .
C6 C 0.8541(3) 0.42473(16) 0.32865(14) 0.0464(5) Uani 1 1 d . . . . .
C7 C 0.7030(3) 0.39005(16) 0.34699(13) 0.0454(5) Uani 1 1 d . . . . .
C8 C 0.6218(3) 0.30587(17) 0.31609(14) 0.0481(5) Uani 1 1 d . . . . .
C9 C 0.6939(3) 0.22026(18) 0.32537(18) 0.0593(6) Uani 1 1 d . . . . .
H9 H 0.7981 0.2158 0.3483 0.071 Uiso 1 1 calc R . . . .
C10 C 0.6117(4) 0.1415(2) 0.3008(2) 0.0694(7) Uani 1 1 d . . . . .
H10 H 0.6607 0.0844 0.3072 0.083 Uiso 1 1 calc R . . . .
C11 C 0.4574(4) 0.1475(2) 0.2669(2) 0.0773(8) Uani 1 1 d . . . . .
H11 H 0.4030 0.0946 0.2496 0.093 Uiso 1 1 calc R . . . .
C12 C 0.3836(4) 0.2318(2) 0.2585(2) 0.0832(9) Uani 1 1 d . . . . .
H12 H 0.2788 0.2358 0.2364 0.100 Uiso 1 1 calc R . . . .
C13 C 0.4655(3) 0.3101(2) 0.2830(2) 0.0664(7) Uani 1 1 d . . . . .
H13 H 0.4151 0.3669 0.2773 0.080 Uiso 1 1 calc R . . . .
C14 C 0.9016(3) 0.46593(14) 0.15602(12) 0.0468(5) Uani 1 1 d . . . . .
C19A C 0.7716(6) 0.4330(3) 0.1072(3) 0.0872(13) Uani 0.335(12) 1 d G . P A 2
H19A H 0.7268 0.3762 0.1201 0.105 Uiso 0.335(12) 1 calc R . P A 2
C18A C 0.7086(6) 0.4850(3) 0.0391(3) 0.0906(15) Uani 0.335(12) 1 d G . P A 2
H18A H 0.6216 0.4630 0.0064 0.109 Uiso 0.335(12) 1 calc R . P A 2
C17 C 0.7756(3) 0.56996(18) 0.01981(13) 0.0639(7) Uani 1 1 d G . . A .
C16 C 0.9056(6) 0.6029(2) 0.0687(3) 0.0695(16) Uani 0.665(12) 1 d G . P A 1
H16 H 0.9504 0.6597 0.0558 0.083 Uiso 0.665(12) 1 calc R . P A 1
C15 C 0.9686(6) 0.5509(3) 0.1368(3) 0.0600(14) Uani 0.665(12) 1 d G . P A 1
H15 H 1.0556 0.5729 0.1694 0.072 Uiso 0.665(12) 1 calc R . P A 1
C15A C 0.9219(14) 0.5586(7) 0.1573(8) 0.0600(14) Uani 0.335(12) 1 d . . P A 2
H15A H 0.9780 0.5878 0.2022 0.072 Uiso 0.335(12) 1 calc R . P A 2
C16A C 0.8569(15) 0.6058(9) 0.0905(8) 0.0695(16) Uani 0.335(12) 1 d . . P A 2
H16A H 0.8681 0.6694 0.0922 0.083 Uiso 0.335(12) 1 calc R . P A 2
C18 C 0.7348(11) 0.4811(4) 0.0318(4) 0.0906(15) Uani 0.665(12) 1 d . . P A 1
H18 H 0.6634 0.4540 -0.0077 0.109 Uiso 0.665(12) 1 calc R . P A 1
C19 C 0.7935(10) 0.4289(4) 0.0994(4) 0.0872(13) Uani 0.665(12) 1 d . . P A 1
H19 H 0.7593 0.3685 0.1062 0.105 Uiso 0.665(12) 1 calc R . P A 1
C20 C 0.7054(5) 0.6270(3) -0.0534(2) 0.0911(11) Uani 1 1 d . . . . .
H20A H 0.6261 0.6683 -0.0310 0.137 Uiso 1 1 calc GR . . A .
H20B H 0.6556 0.5873 -0.0957 0.137 Uiso 1 1 calc GR . . . .
H20C H 0.7898 0.6616 -0.0799 0.137 Uiso 1 1 calc GR . . . .
C21 C 1.2572(4) 0.6816(2) 0.42642(19) 0.0739(8) Uani 1 1 d . . . . .
H21A H 1.2372 0.6985 0.3670 0.111 Uiso 1 1 calc GR . . . .
H21B H 1.2959 0.6196 0.4291 0.111 Uiso 1 1 calc GR . . . .
H21C H 1.3367 0.7221 0.4515 0.111 Uiso 1 1 calc GR . . . .


_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 1.4356(18) . ?
S1 O2 1.4313(18) . ?
S1 C6 1.743(2) . ?
S1 C14 1.7590(17) . ?
O3 C2 1.358(3) . ?
O3 C21 1.422(4) . ?
N1 C1 1.386(3) . ?
N1 C5 1.378(3) . ?
N1 C6 1.397(3) . ?
N2 C5 1.337(3) . ?
N2 C7 1.352(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.358(4) . ?
C2 C3 1.414(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.348(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.411(3) . ?
C6 C7 1.385(3) . ?
C7 C8 1.474(3) . ?
C8 C9 1.389(3) . ?
C8 C13 1.386(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.384(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.376(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.375(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(4) . ?
C13 H13 0.9300 . ?
C14 C19A 1.3900 . ?
C14 C15 1.3900 . ?
C14 C15A 1.360(12) . ?
C14 C19 1.353(5) . ?
C19A H19A 0.9300 . ?
C19A C18A 1.3900 . ?
C18A H18A 0.9300 . ?
C18A C17 1.3900 . ?
C17 C16 1.3900 . ?
C17 C16A 1.375(14) . ?
C17 C18 1.351(6) . ?
C17 C20 1.510(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.3900 . ?
C15 H15 0.9300 . ?
C15A H15A 0.9300 . ?
C15A C16A 1.345(14) . ?
C16A H16A 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.373(6) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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 C6 107.96(11) . . ?
O1 S1 C14 107.79(11) . . ?
O2 S1 O1 119.45(11) . . ?
O2 S1 C6 107.86(11) . . ?
O2 S1 C14 108.47(11) . . ?
C6 S1 C14 104.31(10) . . ?
C2 O3 C21 117.6(2) . . ?
C1 N1 C6 131.9(2) . . ?
C5 N1 C1 122.4(2) . . ?
C5 N1 C6 105.5(2) . . ?
C5 N2 C7 106.4(2) . . ?
N1 C1 H1 120.9 . . ?
C2 C1 N1 118.2(2) . . ?
C2 C1 H1 120.9 . . ?
O3 C2 C3 115.8(2) . . ?
C1 C2 O3 123.8(3) . . ?
C1 C2 C3 120.4(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.2(2) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 118.7(2) . . ?
N2 C5 N1 111.6(2) . . ?
N2 C5 C4 129.6(2) . . ?
N1 C6 S1 121.82(17) . . ?
C7 C6 S1 129.94(18) . . ?
C7 C6 N1 106.27(19) . . ?
N2 C7 C6 110.2(2) . . ?
N2 C7 C8 119.4(2) . . ?
C6 C7 C8 130.3(2) . . ?
C9 C8 C7 121.3(2) . . ?
C13 C8 C7 120.0(2) . . ?
C13 C8 C9 118.4(2) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C8 C13 H13 119.4 . . ?
C12 C13 C8 121.1(3) . . ?
C12 C13 H13 119.4 . . ?
C19A C14 S1 120.11(14) . . ?
C15 C14 S1 119.89(14) . . ?
C15A C14 S1 118.7(5) . . ?
C15A C14 C19A 116.4(5) . . ?
C19 C14 S1 120.7(2) . . ?
C19 C14 C15 118.6(2) . . ?
C14 C19A H19A 120.0 . . ?
C14 C19A C18A 120.0 . . ?
C18A C19A H19A 120.0 . . ?
C19A C18A H18A 120.0 . . ?
C17 C18A C19A 120.0 . . ?
C17 C18A H18A 120.0 . . ?
C18A C17 C20 119.9(2) . . ?
C16 C17 C20 120.1(2) . . ?
C16A C17 C18A 111.2(5) . . ?
C16A C17 C20 124.1(6) . . ?
C18 C17 C16 116.7(3) . . ?
C18 C17 C20 122.3(3) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15A H15A 121.7 . . ?
C16A C15A C14 116.6(10) . . ?
C16A C15A H15A 121.7 . . ?
C17 C16A H16A 116.6 . . ?
C15A C16A C17 126.7(11) . . ?
C15A C16A H16A 116.6 . . ?
C17 C18 H18 118.4 . . ?
C17 C18 C19 123.2(4) . . ?
C19 C18 H18 118.4 . . ?
C14 C19 C18 119.5(4) . . ?
C14 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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 C6 C7 N2 -163.92(17) . . . . ?
S1 C6 C7 C8 19.4(4) . . . . ?
S1 C14 C19A C18A 179.61(14) . . . . ?
S1 C14 C15 C16 -179.61(14) . . . . ?
S1 C14 C15A C16A -178.9(7) . . . . ?
S1 C14 C19 C18 -179.3(5) . . . . ?
O1 S1 C6 N1 32.4(2) . . . . ?
O1 S1 C6 C7 -165.9(2) . . . . ?
O1 S1 C14 C19A 163.3(4) . . . . ?
O1 S1 C14 C15 -17.1(4) . . . . ?
O1 S1 C14 C15A -42.0(6) . . . . ?
O1 S1 C14 C19 152.4(5) . . . . ?
O2 S1 C6 N1 162.73(17) . . . . ?
O2 S1 C6 C7 -35.5(2) . . . . ?
O2 S1 C14 C19A 32.6(4) . . . . ?
O2 S1 C14 C15 -147.8(4) . . . . ?
O2 S1 C14 C15A -172.6(6) . . . . ?
O2 S1 C14 C19 21.7(6) . . . . ?
O3 C2 C3 C4 -179.1(2) . . . . ?
N1 C1 C2 O3 177.3(2) . . . . ?
N1 C1 C2 C3 -0.5(3) . . . . ?
N1 C6 C7 N2 0.0(2) . . . . ?
N1 C6 C7 C8 -176.7(2) . . . . ?
N2 C7 C8 C9 -121.8(2) . . . . ?
N2 C7 C8 C13 53.2(3) . . . . ?
C1 N1 C5 N2 -176.85(19) . . . . ?
C1 N1 C5 C4 -0.9(3) . . . . ?
C1 N1 C6 S1 -18.8(3) . . . . ?
C1 N1 C6 C7 175.7(2) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C2 C3 C4 C5 1.7(4) . . . . ?
C3 C4 C5 N1 -0.7(4) . . . . ?
C3 C4 C5 N2 174.4(2) . . . . ?
C5 N1 C1 C2 1.5(3) . . . . ?
C5 N1 C6 S1 166.32(16) . . . . ?
C5 N1 C6 C7 0.8(2) . . . . ?
C5 N2 C7 C6 -0.8(3) . . . . ?
C5 N2 C7 C8 176.27(19) . . . . ?
C6 S1 C14 C19A -82.2(4) . . . . ?
C6 S1 C14 C15 97.4(4) . . . . ?
C6 S1 C14 C15A 72.6(6) . . . . ?
C6 S1 C14 C19 -93.1(5) . . . . ?
C6 N1 C1 C2 -172.7(2) . . . . ?
C6 N1 C5 N2 -1.4(2) . . . . ?
C6 N1 C5 C4 174.6(2) . . . . ?
C6 C7 C8 C9 54.6(3) . . . . ?
C6 C7 C8 C13 -130.4(3) . . . . ?
C7 N2 C5 N1 1.4(3) . . . . ?
C7 N2 C5 C4 -174.1(2) . . . . ?
C7 C8 C9 C10 176.0(2) . . . . ?
C7 C8 C13 C12 -176.1(3) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C9 C8 C13 C12 -1.0(4) . . . . ?
C9 C10 C11 C12 -1.0(5) . . . . ?
C10 C11 C12 C13 1.0(5) . . . . ?
C11 C12 C13 C8 0.1(5) . . . . ?
C13 C8 C9 C10 1.0(4) . . . . ?
C14 S1 C6 N1 -82.08(19) . . . . ?
C14 S1 C6 C7 79.7(2) . . . . ?
C14 C19A C18A C17 0.0 . . . . ?
C14 C15A C16A C17 -1.8(15) . . . . ?
C19A C14 C15A C16A -23.2(11) . . . . ?
C19A C18A C17 C16A -22.6(5) . . . . ?
C19A C18A C17 C20 -179.1(3) . . . . ?
C18A C17 C16A C15A 24.8(12) . . . . ?
C17 C16 C15 C14 0.0 . . . . ?
C17 C18 C19 C14 -2.2(10) . . . . ?
C16 C17 C18 C19 12.6(11) . . . . ?
C15 C14 C19 C18 -9.7(10) . . . . ?
C15A C14 C19A C18A 24.3(5) . . . . ?
C18 C17 C16 C15 -11.3(8) . . . . ?
C19 C14 C15 C16 10.7(8) . . . . ?
C20 C17 C16 C15 179.1(3) . . . . ?
C20 C17 C16A C15A -179.9(8) . . . . ?
C20 C17 C18 C19 -178.0(5) . . . . ?
C21 O3 C2 C1 0.6(4) . . . . ?
C21 O3 C2 C3 178.6(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 1.312
_oxdiff_exptl_absorpt_empirical_full_min 0.883
####################################################################### 
# 
# 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_202007109
_database_code_depnum_ccdc_archive 'CCDC 2046841'
loop_
_audit_author_name
_audit_author_address
'Han LiLi'
;Zhengzhou University
China
;
_audit_update_record             
;
2020-11-27 deposited with the CCDC.	2021-04-02 downloaded from the CCDC.
;
_audit_creation_date             2020-07-24
_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         'C21 H18 N2 O2 S'
_chemical_formula_sum            'C21 H18 N2 O2 S'
_chemical_formula_weight         362.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H15N2O4S1
_chemical_oxdiff_usercomment     r
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/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                   9.3338(3)
_cell_length_b                   15.3970(4)
_cell_length_c                   12.9510(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.887(3)
_cell_angle_gamma                90
_cell_volume                     1856.95(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2285
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7390
_cell_measurement_theta_min      5.5340
_shelx_estimated_absorpt_T_max   0.836
_shelx_estimated_absorpt_T_min   0.740
_exptl_absorpt_coefficient_mu    1.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6984
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.066
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         4.467
_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 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   -100.00 -43.00   1.00    1.00    --  -33.50 178.00  60.00   57
  2  ω     40.00  66.00   1.00    1.00    --   36.47 -99.00-180.00   26
  3  ω     63.00  89.00   1.00    1.00    --   36.47  37.00 -60.00   26
  4  ω     -4.00  46.00   1.00    1.00    --   36.47 -99.00  90.00   50
  5  ω     21.00 103.00   1.00    1.00    --   36.47  57.00   0.00   82
  6  ω     54.00 105.00   1.00    1.00    --   36.47  57.00 120.00   51
  7  ω    -13.00  59.00   1.00    1.00    --   36.47 -37.00-180.00   72
  8  ω    124.00 171.00   1.00    3.50    --  108.00  45.00-120.00   47
  9  ω     89.00 129.00   1.00    3.50    --  108.00  30.00  30.00   40
 10  ω     43.00  69.00   1.00    3.50    --  108.00 -94.00-120.00   26
 11  ω     40.00 117.00   1.00    3.50    --  108.00 -61.00-180.00   77
 12  ω     38.00 133.00   1.00    3.50    --  108.00 -30.00  60.00   95
 13  ω    140.00 173.00   1.00    3.50    --  108.00  30.00  30.00   33
 14  ω     45.00  95.00   1.00    3.50    --  108.00 -94.00 120.00   50
 15  ω     46.00 110.00   1.00    3.50    --  108.00 -94.00 -30.00   64
 16  ω     70.00 105.00   1.00    3.50    --  108.00 -94.00-120.00   35
 17  ω     63.00 126.00   1.00    3.50    --  108.00 -30.00-150.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1158113000
_diffrn_orient_matrix_UB_12      -0.0563632000
_diffrn_orient_matrix_UB_13      0.0579916000
_diffrn_orient_matrix_UB_21      -0.0863597000
_diffrn_orient_matrix_UB_22      0.0017143000
_diffrn_orient_matrix_UB_23      0.0971543000
_diffrn_orient_matrix_UB_31      -0.0805787000
_diffrn_orient_matrix_UB_32      -0.0827347000
_diffrn_orient_matrix_UB_33      -0.0373671000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2670
_reflns_number_total             3308
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (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         0.190
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0484
_refine_ls_restrained_S_all      1.043
_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)+(0.0721P)²+0.2037P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1360
_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.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C12(H12), C13(H13),
 C15(H15), C16(H16), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_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
S1 S 0.29767(7) 0.81142(4) 0.38001(4) 0.05055(19) Uani 1 1 d . . . . .
O1 O 0.1459(2) 0.79509(14) 0.36708(15) 0.0699(6) Uani 1 1 d . . . . .
O2 O 0.3466(3) 0.89359(12) 0.41881(14) 0.0729(6) Uani 1 1 d . . . . .
N1 N 0.33624(19) 0.72292(12) 0.20225(13) 0.0421(4) Uani 1 1 d . . . . .
N2 N 0.47349(19) 0.80829(12) 0.10927(13) 0.0428(4) Uani 1 1 d . . . . .
C1 C 0.2512(3) 0.65224(16) 0.2191(2) 0.0558(6) Uani 1 1 d . . . . .
H1 H 0.2015 0.6486 0.2789 0.067 Uiso 1 1 calc R . . . .
C2 C 0.2407(3) 0.58832(17) 0.1482(2) 0.0632(7) Uani 1 1 d . . . . .
H2 H 0.1837 0.5401 0.1591 0.076 Uiso 1 1 calc R . . . .
C3 C 0.3150(3) 0.59388(17) 0.0577(2) 0.0628(7) Uani 1 1 d . . . . .
H3 H 0.3095 0.5483 0.0105 0.075 Uiso 1 1 calc R . . . .
C4 C 0.3947(3) 0.66465(17) 0.03834(18) 0.0551(6) Uani 1 1 d . . . . .
H4 H 0.4421 0.6684 -0.0224 0.066 Uiso 1 1 calc R . . . .
C5 C 0.4048(2) 0.73278(14) 0.11147(16) 0.0421(5) Uani 1 1 d . . . . .
C6 C 0.3694(2) 0.79702(14) 0.26030(16) 0.0417(5) Uani 1 1 d . . . . .
C7 C 0.4544(2) 0.84831(14) 0.20084(15) 0.0400(4) Uani 1 1 d . . . . .
C8 C 0.5168(2) 0.93534(14) 0.21873(16) 0.0424(5) Uani 1 1 d . . . . .
C9 C 0.5995(3) 0.95849(17) 0.3073(2) 0.0630(7) Uani 1 1 d . . . . .
H9 H 0.6133 0.9188 0.3612 0.076 Uiso 1 1 calc R . . . .
C10 C 0.6614(4) 1.0396(2) 0.3164(2) 0.0721(8) Uani 1 1 d . . . . .
H10 H 0.7164 1.0535 0.3768 0.087 Uiso 1 1 calc R . . . .
C11 C 0.6443(3) 1.10082(17) 0.2387(2) 0.0596(6) Uani 1 1 d . . . . .
C12 C 0.5617(3) 1.07775(15) 0.15026(18) 0.0496(5) Uani 1 1 d . . . . .
H12 H 0.5483 1.1175 0.0964 0.059 Uiso 1 1 calc R . . . .
C13 C 0.4988(2) 0.99694(14) 0.14047(16) 0.0439(5) Uani 1 1 d . . . . .
H13 H 0.4431 0.9834 0.0803 0.053 Uiso 1 1 calc R . . . .
C14 C 0.3751(2) 0.72807(14) 0.45938(16) 0.0439(5) Uani 1 1 d . . . . .
C15 C 0.2866(3) 0.67077(18) 0.50636(19) 0.0540(6) Uani 1 1 d . . . . .
H15 H 0.1874 0.6743 0.4943 0.065 Uiso 1 1 calc R . . . .
C16 C 0.3476(3) 0.60777(17) 0.5719(2) 0.0585(6) Uani 1 1 d . . . . .
H16 H 0.2881 0.5696 0.6045 0.070 Uiso 1 1 calc R . . . .
C17 C 0.4945(3) 0.60025(16) 0.59004(18) 0.0541(6) Uani 1 1 d . . . . .
C18 C 0.5801(3) 0.65765(19) 0.5403(2) 0.0656(7) Uani 1 1 d . . . . .
H18 H 0.6794 0.6529 0.5504 0.079 Uiso 1 1 calc R . . . .
C19 C 0.5228(3) 0.72131(18) 0.4765(2) 0.0610(7) Uani 1 1 d . . . . .
H19 H 0.5827 0.7599 0.4448 0.073 Uiso 1 1 calc R . . . .
C20 C 0.5588(4) 0.5315(2) 0.6620(2) 0.0765(9) Uani 1 1 d . . . . .
H20A H 0.5501 0.5491 0.7324 0.115 Uiso 1 1 calc GR . . . .
H20B H 0.6584 0.5240 0.6500 0.115 Uiso 1 1 calc GR . . . .
H20C H 0.5089 0.4776 0.6495 0.115 Uiso 1 1 calc GR . . . .
C21 C 0.7110(5) 1.1899(2) 0.2505(3) 0.0919(12) Uani 1 1 d . . . . .
H21A H 0.7901 1.1943 0.2070 0.138 Uiso 1 1 calc GR . . . .
H21B H 0.7449 1.1988 0.3213 0.138 Uiso 1 1 calc GR . . . .
H21C H 0.6405 1.2332 0.2305 0.138 Uiso 1 1 calc GR . . . .


_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 1.437(2) . ?
S1 O2 1.425(2) . ?
S1 C6 1.744(2) . ?
S1 C14 1.768(2) . ?
N1 C1 1.373(3) . ?
N1 C5 1.384(3) . ?
N1 C6 1.390(3) . ?
N2 C5 1.329(3) . ?
N2 C7 1.359(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.346(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.405(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.352(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.412(3) . ?
C6 C7 1.389(3) . ?
C7 C8 1.473(3) . ?
C8 C9 1.385(3) . ?
C8 C13 1.390(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.378(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.381(4) . ?
C11 C12 1.383(3) . ?
C11 C21 1.510(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(3) . ?
C14 C19 1.385(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.380(4) . ?
C17 C18 1.380(4) . ?
C17 C20 1.508(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.367(4) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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 C6 107.99(11) . . ?
O1 S1 C14 107.57(11) . . ?
O2 S1 O1 119.10(13) . . ?
O2 S1 C6 107.04(11) . . ?
O2 S1 C14 109.31(12) . . ?
C6 S1 C14 104.96(10) . . ?
C1 N1 C5 121.85(19) . . ?
C1 N1 C6 132.41(19) . . ?
C5 N1 C6 105.70(17) . . ?
C5 N2 C7 106.62(17) . . ?
N1 C1 H1 120.4 . . ?
C2 C1 N1 119.1(2) . . ?
C2 C1 H1 120.4 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.5(2) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.2(2) . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 118.3(2) . . ?
N2 C5 N1 111.45(18) . . ?
N2 C5 C4 130.2(2) . . ?
N1 C6 S1 120.02(16) . . ?
C7 C6 S1 133.54(17) . . ?
C7 C6 N1 106.35(18) . . ?
N2 C7 C6 109.85(19) . . ?
N2 C7 C8 118.42(18) . . ?
C6 C7 C8 131.65(19) . . ?
C9 C8 C7 123.8(2) . . ?
C9 C8 C13 117.5(2) . . ?
C13 C8 C7 118.62(19) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.0 . . ?
C9 C10 C11 121.9(2) . . ?
C11 C10 H10 119.0 . . ?
C10 C11 C12 117.3(2) . . ?
C10 C11 C21 121.4(3) . . ?
C12 C11 C21 121.3(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.2(2) . . ?
C13 C12 H12 119.4 . . ?
C8 C13 H13 119.4 . . ?
C12 C13 C8 121.3(2) . . ?
C12 C13 H13 119.4 . . ?
C15 C14 S1 119.17(18) . . ?
C15 C14 C19 120.1(2) . . ?
C19 C14 S1 120.74(17) . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 119.0(2) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.7(2) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 C18 117.8(2) . . ?
C16 C17 C20 120.9(2) . . ?
C18 C17 C20 121.3(3) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 C17 121.7(2) . . ?
C19 C18 H18 119.1 . . ?
C14 C19 H19 120.2 . . ?
C18 C19 C14 119.7(2) . . ?
C18 C19 H19 120.2 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C11 C21 H21A 109.5 . . ?
C11 C21 H21B 109.5 . . ?
C11 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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 C6 C7 N2 -176.25(17) . . . . ?
S1 C6 C7 C8 0.5(4) . . . . ?
S1 C14 C15 C16 -177.4(2) . . . . ?
S1 C14 C19 C18 178.4(2) . . . . ?
O1 S1 C6 N1 -48.8(2) . . . . ?
O1 S1 C6 C7 127.3(2) . . . . ?
O1 S1 C14 C15 -8.5(2) . . . . ?
O1 S1 C14 C19 173.1(2) . . . . ?
O2 S1 C6 N1 -178.12(18) . . . . ?
O2 S1 C6 C7 -2.1(3) . . . . ?
O2 S1 C14 C15 122.2(2) . . . . ?
O2 S1 C14 C19 -56.3(2) . . . . ?
N1 C1 C2 C3 -0.3(4) . . . . ?
N1 C6 C7 N2 0.2(2) . . . . ?
N1 C6 C7 C8 177.0(2) . . . . ?
N2 C7 C8 C9 -130.7(2) . . . . ?
N2 C7 C8 C13 45.8(3) . . . . ?
C1 N1 C5 N2 176.0(2) . . . . ?
C1 N1 C5 C4 -4.8(3) . . . . ?
C1 N1 C6 S1 0.5(3) . . . . ?
C1 N1 C6 C7 -176.5(2) . . . . ?
C1 C2 C3 C4 -2.2(4) . . . . ?
C2 C3 C4 C5 1.3(4) . . . . ?
C3 C4 C5 N1 2.2(3) . . . . ?
C3 C4 C5 N2 -178.8(2) . . . . ?
C5 N1 C1 C2 3.9(4) . . . . ?
C5 N1 C6 S1 177.90(15) . . . . ?
C5 N1 C6 C7 0.9(2) . . . . ?
C5 N2 C7 C6 -1.2(2) . . . . ?
C5 N2 C7 C8 -178.48(18) . . . . ?
C6 S1 C14 C15 -123.3(2) . . . . ?
C6 S1 C14 C19 58.3(2) . . . . ?
C6 N1 C1 C2 -179.1(2) . . . . ?
C6 N1 C5 N2 -1.7(2) . . . . ?
C6 N1 C5 C4 177.5(2) . . . . ?
C6 C7 C8 C9 52.8(4) . . . . ?
C6 C7 C8 C13 -130.8(2) . . . . ?
C7 N2 C5 N1 1.8(2) . . . . ?
C7 N2 C5 C4 -177.2(2) . . . . ?
C7 C8 C9 C10 176.2(3) . . . . ?
C7 C8 C13 C12 -176.2(2) . . . . ?
C8 C9 C10 C11 0.0(5) . . . . ?
C9 C8 C13 C12 0.5(3) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C9 C10 C11 C21 179.1(3) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C11 C12 C13 C8 -0.5(4) . . . . ?
C13 C8 C9 C10 -0.3(4) . . . . ?
C14 S1 C6 N1 65.78(19) . . . . ?
C14 S1 C6 C7 -118.2(2) . . . . ?
C14 C15 C16 C17 -0.9(4) . . . . ?
C15 C14 C19 C18 -0.1(4) . . . . ?
C15 C16 C17 C18 -0.2(4) . . . . ?
C15 C16 C17 C20 179.7(3) . . . . ?
C16 C17 C18 C19 1.3(4) . . . . ?
C17 C18 C19 C14 -1.2(5) . . . . ?
C19 C14 C15 C16 1.1(4) . . . . ?
C20 C17 C18 C19 -178.6(3) . . . . ?
C21 C11 C12 C13 -178.8(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 1.146
_oxdiff_exptl_absorpt_empirical_full_min 0.906
