# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 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_guoshq_0605
_database_code_depnum_ccdc_archive 'CCDC 2073620'
loop_
_audit_author_name
_audit_author_address
'shengqiang guo'
;Lanzhou University
China
;
_audit_update_record             
;
2021-03-27 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;
_audit_creation_date             2020-06-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 Cl F N4 O2 S'
_chemical_formula_sum            'C22 H19 Cl F N4 O2 S'
_chemical_formula_weight         457.92
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.17026(19)
_cell_length_b                   21.7971(5)
_cell_length_c                   13.6848(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.637(3)
_cell_angle_gamma                90
_cell_volume                     2114.56(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3105
_cell_measurement_temperature    293.1(2)
_cell_measurement_theta_max      69.5310
_cell_measurement_theta_min      6.9120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.837
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7622
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.592
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         3.845
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.1(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  16.00   1.00    1.00    --    0.00  57.00  30.00   25
  2  ω     30.00  68.00   1.00    1.00    --    0.00  57.00  90.00   38
  3  ω     25.00 121.00   1.00    1.00    --   54.00  19.00 -30.00   96
  4  ω     76.00 123.00   1.00    2.00    --  108.00 -38.00 -60.00   47
  5  ω    103.00 164.00   1.00    2.00    --  108.00  38.00-150.00   61
  6  ω     92.00 176.00   1.00    2.00    --  108.00  63.00-120.00   84
  7  ω    119.00 145.00   1.00    2.00    --  108.00 111.00   0.00   26
  8  ω     34.00 124.00   1.00    1.00    --   54.00  38.00-150.00   90
  9  ω     39.00  66.00   1.00    2.00    --  108.00 -38.00 -60.00   27
 10  ω     42.00 129.00   1.00    2.00    --  108.00 -77.00   0.00   87
 11  ω     38.00 124.00   1.00    2.00    --  108.00 -50.00  90.00   86
 12  ω     36.00  62.00   1.00    2.00    --  108.00-111.00 -30.00   26
 13  ω     31.00 111.00   1.00    1.00    --   54.00-125.00   0.00   80
 14  ω     53.00 116.00   1.00    2.00    --  108.00-111.00-180.00   63
 15  ω    -20.00  16.00   1.00    1.00    --    0.00  57.00-150.00   36
 16  ω     -1.00  25.00   1.00    1.00    --    0.00  57.00  90.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0605163000
_diffrn_orient_matrix_UB_12      -0.0373976000
_diffrn_orient_matrix_UB_13      0.0854728000
_diffrn_orient_matrix_UB_21      -0.2033764000
_diffrn_orient_matrix_UB_22      -0.0028331000
_diffrn_orient_matrix_UB_23      -0.0555167000
_diffrn_orient_matrix_UB_31      0.0474888000
_diffrn_orient_matrix_UB_32      -0.0598779000
_diffrn_orient_matrix_UB_33      -0.0507052000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3148
_reflns_number_total             3737
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3737
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0545
_refine_ls_restrained_S_all      1.040
_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)+(0.0829P)²+0.9638P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1552
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C19(H19), C2(H2), C20(H20), C10(H10), C6(H6), C21(H21), C5(H5),
 C13(H13), C11(H11), C12(H12), C18(H18)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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
Cl1 Cl 0.2310(3) 0.31771(4) 0.04428(7) 0.1404(7) Uani 1 1 d . . . . .
S1 S 0.30251(9) 0.07286(3) 0.01759(4) 0.0484(2) Uani 1 1 d . . . . .
F1 F -0.1615(5) 0.28428(16) 0.0692(2) 0.1676(17) Uani 1 1 d . . . . .
O2 O 0.4916(3) 0.08340(11) 0.06531(16) 0.0729(7) Uani 1 1 d . . . . .
O1 O 0.2064(4) 0.01995(10) 0.04749(16) 0.0803(7) Uani 1 1 d . . . . .
N1 N 0.0246(3) 0.11815(9) -0.18122(14) 0.0397(4) Uani 1 1 d . . . . .
N3 N -0.4244(3) 0.18159(12) -0.19622(19) 0.0592(6) Uani 1 1 d . . . . .
N2 N -0.2371(3) 0.17733(10) -0.20603(15) 0.0429(5) Uani 1 1 d . . . . .
N4 N -0.4673(3) 0.23909(13) -0.1897(2) 0.0672(7) Uani 1 1 d . . . . .
C1 C 0.1665(4) 0.13805(12) 0.03386(18) 0.0465(6) Uani 1 1 d . . . . .
C17 C -0.1595(3) 0.23482(11) -0.20495(16) 0.0417(5) Uani 1 1 d . . . . .
C14 C 0.1989(4) 0.08321(13) -0.3494(2) 0.0547(6) Uani 1 1 d . . . . .
H14 H 0.190912 0.124812 -0.335523 0.066 Uiso 1 1 calc R U . . .
C7 C 0.3127(3) 0.06680(11) -0.11059(17) 0.0405(5) Uani 1 1 d . . . . .
H7A H 0.374088 0.103293 -0.130937 0.049 Uiso 1 1 calc R U . . .
H7B H 0.392233 0.032066 -0.120630 0.049 Uiso 1 1 calc R U . . .
C3 C 0.1356(7) 0.24596(15) 0.0447(2) 0.0796(11) Uani 1 1 d . . . . .
C19 C 0.0374(5) 0.31968(14) -0.2172(2) 0.0620(7) Uani 1 1 d . . . . .
H19 H 0.153318 0.336514 -0.225217 0.074 Uiso 1 1 calc R U . . .
C2 C 0.2474(5) 0.19468(12) 0.03236(19) 0.0568(7) Uani 1 1 d . . . . .
H2 H 0.372752 0.199052 0.023426 0.068 Uiso 1 1 calc R U . . .
C20 C -0.1132(5) 0.35929(14) -0.2071(2) 0.0703(9) Uani 1 1 d . . . . .
H20 H -0.094191 0.401468 -0.208521 0.084 Uiso 1 1 calc R U . . .
C4 C -0.0498(7) 0.2363(2) 0.0572(2) 0.0892(14) Uani 1 1 d . . . . .
C10 C 0.1759(5) -0.02110(14) -0.3029(2) 0.0716(9) Uani 1 1 d . . . . .
H10 H 0.152316 -0.050556 -0.257149 0.086 Uiso 1 1 calc R U . . .
C6 C -0.0203(4) 0.12997(17) 0.0469(2) 0.0635(8) Uani 1 1 d . . . . .
H6 H -0.070998 0.090691 0.046757 0.076 Uiso 1 1 calc R U . . .
C21 C -0.2856(5) 0.33746(15) -0.1953(2) 0.0666(8) Uani 1 1 d . . . . .
H21 H -0.384301 0.363829 -0.187641 0.080 Uiso 1 1 calc R U . . .
C8 C 0.1248(3) 0.05911(10) -0.17877(17) 0.0393(5) Uani 1 1 d . . . . .
H8 H 0.049777 0.027202 -0.152507 0.047 Uiso 1 1 calc R U . . .
C5 C -0.1287(5) 0.1795(2) 0.0599(3) 0.0876(13) Uani 1 1 d . . . . .
H5 H -0.253139 0.174774 0.070307 0.105 Uiso 1 1 calc R U . . .
C15 C -0.1509(3) 0.11837(11) -0.20837(17) 0.0396(5) Uani 1 1 d . . . . .
C13 C 0.2443(5) 0.06456(19) -0.4395(2) 0.0721(9) Uani 1 1 d . . . . .
H13 H 0.268591 0.093711 -0.485599 0.087 Uiso 1 1 calc R U . . .
C9 C 0.1657(3) 0.04033(11) -0.28009(18) 0.0414(5) Uani 1 1 d . . . . .
C11 C 0.2210(6) -0.03918(18) -0.3932(3) 0.0895(13) Uani 1 1 d . . . . .
H11 H 0.229107 -0.080702 -0.407651 0.107 Uiso 1 1 calc R U . . .
C22 C -0.3091(4) 0.27385(13) -0.19527(19) 0.0525(6) Uani 1 1 d . . . . .
C12 C 0.2536(5) 0.0035(2) -0.4613(2) 0.0816(11) Uani 1 1 d . . . . .
H12 H 0.282081 -0.008772 -0.522404 0.098 Uiso 1 1 calc R U . . .
C18 C 0.0194(4) 0.25711(13) -0.21551(18) 0.0494(6) Uani 1 1 d . . . . .
H18 H 0.119923 0.231045 -0.221071 0.059 Uiso 1 1 calc R U . . .
C16 C -0.2798(4) 0.06685(13) -0.2451(2) 0.0550(7) Uani 1 1 d . . . . .
H16A H -0.217475 0.040026 -0.285478 0.082 Uiso 1 1 calc R U . . .
H16B H -0.392056 0.083057 -0.283509 0.082 Uiso 1 1 calc R U . . .
H16C H -0.312921 0.044338 -0.189880 0.082 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C3 1.707(4) . ?
S1 O2 1.432(2) . ?
S1 O1 1.434(2) . ?
S1 C1 1.756(2) . ?
S1 C7 1.771(2) . ?
F1 C4 1.342(4) . ?
N1 C8 1.472(3) . ?
N1 C15 1.257(3) . ?
N3 N2 1.372(3) . ?
N3 N4 1.297(4) . ?
N2 C17 1.370(3) . ?
N2 C15 1.429(3) . ?
N4 C22 1.376(4) . ?
C1 C2 1.365(4) . ?
C1 C6 1.389(4) . ?
C17 C22 1.391(3) . ?
C17 C18 1.399(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.383(4) . ?
C14 C9 1.378(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.528(3) . ?
C3 C2 1.400(4) . ?
C3 C4 1.382(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.405(5) . ?
C19 C18 1.371(4) . ?
C2 H2 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.357(5) . ?
C4 C5 1.365(6) . ?
C10 H10 0.9300 . ?
C10 C9 1.379(4) . ?
C10 C11 1.381(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.357(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.397(4) . ?
C8 H8 0.9800 . ?
C8 C9 1.516(3) . ?
C5 H5 0.9300 . ?
C15 C16 1.493(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.367(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.362(6) . ?
C12 H12 0.9300 . ?
C18 H18 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
O2 S1 O1 117.47(15) . . ?
O2 S1 C1 108.54(13) . . ?
O2 S1 C7 106.65(13) . . ?
O1 S1 C1 108.34(14) . . ?
O1 S1 C7 108.39(13) . . ?
C1 S1 C7 106.98(11) . . ?
C15 N1 C8 118.3(2) . . ?
N4 N3 N2 108.6(2) . . ?
N3 N2 C15 119.8(2) . . ?
C17 N2 N3 109.8(2) . . ?
C17 N2 C15 130.28(19) . . ?
N3 N4 C22 108.8(2) . . ?
C2 C1 S1 119.0(2) . . ?
C2 C1 C6 122.5(3) . . ?
C6 C1 S1 118.6(2) . . ?
N2 C17 C22 104.0(2) . . ?
N2 C17 C18 133.9(2) . . ?
C22 C17 C18 122.0(3) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
C9 C14 C13 120.2(3) . . ?
S1 C7 H7A 108.1 . . ?
S1 C7 H7B 108.1 . . ?
H7A C7 H7B 107.3 . . ?
C8 C7 S1 116.68(16) . . ?
C8 C7 H7A 108.1 . . ?
C8 C7 H7B 108.1 . . ?
C2 C3 Cl1 119.6(4) . . ?
C4 C3 Cl1 122.2(3) . . ?
C4 C3 C2 118.2(3) . . ?
C20 C19 H19 118.9 . . ?
C18 C19 H19 118.9 . . ?
C18 C19 C20 122.3(3) . . ?
C1 C2 C3 117.9(3) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.6(3) . . ?
C21 C20 H20 119.2 . . ?
F1 C4 C3 119.9(5) . . ?
F1 C4 C5 116.5(5) . . ?
C5 C4 C3 123.5(3) . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.5(3) . . ?
C11 C10 H10 119.8 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 119.9(4) . . ?
C5 C6 H6 120.0 . . ?
C20 C21 H21 121.3 . . ?
C20 C21 C22 117.4(3) . . ?
C22 C21 H21 121.3 . . ?
N1 C8 C7 107.49(18) . . ?
N1 C8 H8 109.6 . . ?
N1 C8 C9 112.09(18) . . ?
C7 C8 H8 109.6 . . ?
C9 C8 C7 108.31(18) . . ?
C9 C8 H8 109.6 . . ?
C4 C5 H5 121.0 . . ?
C6 C5 C4 118.1(4) . . ?
C6 C5 H5 121.0 . . ?
N1 C15 N2 114.5(2) . . ?
N1 C15 C16 129.7(2) . . ?
N2 C15 C16 115.8(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 C14 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C9 C10 118.8(3) . . ?
C14 C9 C8 121.6(2) . . ?
C10 C9 C8 119.6(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.9 . . ?
N4 C22 C17 108.8(2) . . ?
N4 C22 C21 130.3(3) . . ?
C17 C22 C21 120.8(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 C13 119.8(3) . . ?
C11 C12 H12 120.1 . . ?
C17 C18 H18 122.0 . . ?
C19 C18 C17 115.9(3) . . ?
C19 C18 H18 122.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
Cl1 C3 C2 C1 179.5(2) . . . . ?
Cl1 C3 C4 F1 0.2(4) . . . . ?
Cl1 C3 C4 C5 -178.6(3) . . . . ?
S1 C1 C2 C3 179.49(19) . . . . ?
S1 C1 C6 C5 179.8(2) . . . . ?
S1 C7 C8 N1 71.5(2) . . . . ?
S1 C7 C8 C9 -167.18(16) . . . . ?
F1 C4 C5 C6 179.3(3) . . . . ?
O2 S1 C1 C2 36.4(2) . . . . ?
O2 S1 C1 C6 -144.1(2) . . . . ?
O2 S1 C7 C8 -176.54(17) . . . . ?
O1 S1 C1 C2 165.0(2) . . . . ?
O1 S1 C1 C6 -15.5(2) . . . . ?
O1 S1 C7 C8 56.1(2) . . . . ?
N1 C8 C9 C14 31.7(3) . . . . ?
N1 C8 C9 C10 -150.4(2) . . . . ?
N3 N2 C17 C22 -0.7(3) . . . . ?
N3 N2 C17 C18 -177.4(3) . . . . ?
N3 N2 C15 N1 -155.0(2) . . . . ?
N3 N2 C15 C16 26.7(3) . . . . ?
N3 N4 C22 C17 -0.6(3) . . . . ?
N3 N4 C22 C21 177.4(3) . . . . ?
N2 N3 N4 C22 0.1(3) . . . . ?
N2 C17 C22 N4 0.8(3) . . . . ?
N2 C17 C22 C21 -177.4(2) . . . . ?
N2 C17 C18 C19 175.3(3) . . . . ?
N4 N3 N2 C17 0.4(3) . . . . ?
N4 N3 N2 C15 176.0(2) . . . . ?
C1 S1 C7 C8 -60.5(2) . . . . ?
C1 C6 C5 C4 1.6(5) . . . . ?
C17 N2 C15 N1 19.6(3) . . . . ?
C17 N2 C15 C16 -158.7(2) . . . . ?
C14 C13 C12 C11 -1.1(5) . . . . ?
C7 S1 C1 C2 -78.3(2) . . . . ?
C7 S1 C1 C6 101.1(2) . . . . ?
C7 C8 C9 C14 -86.7(3) . . . . ?
C7 C8 C9 C10 91.2(3) . . . . ?
C3 C4 C5 C6 -1.8(5) . . . . ?
C19 C20 C21 C22 -1.1(5) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
C2 C3 C4 F1 -180.0(3) . . . . ?
C2 C3 C4 C5 1.2(5) . . . . ?
C20 C19 C18 C17 1.1(4) . . . . ?
C20 C21 C22 N4 -176.6(3) . . . . ?
C20 C21 C22 C17 1.2(4) . . . . ?
C4 C3 C2 C1 -0.3(4) . . . . ?
C10 C11 C12 C13 0.9(6) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
C8 N1 C15 N2 178.44(19) . . . . ?
C8 N1 C15 C16 -3.5(4) . . . . ?
C15 N1 C8 C7 -159.9(2) . . . . ?
C15 N1 C8 C9 81.2(3) . . . . ?
C15 N2 C17 C22 -175.7(2) . . . . ?
C15 N2 C17 C18 7.6(4) . . . . ?
C13 C14 C9 C10 -0.9(4) . . . . ?
C13 C14 C9 C8 177.1(3) . . . . ?
C9 C14 C13 C12 1.0(5) . . . . ?
C9 C10 C11 C12 -0.8(6) . . . . ?
C11 C10 C9 C14 0.8(5) . . . . ?
C11 C10 C9 C8 -177.2(3) . . . . ?
C22 C17 C18 C19 -0.9(4) . . . . ?
C18 C17 C22 N4 178.0(2) . . . . ?
C18 C17 C22 C21 -0.3(4) . . . . ?
C18 C19 C20 C21 -0.1(5) . . . . ?

_olex2_date_sample_data_collection 2020-06-05
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.122
_oxdiff_exptl_absorpt_empirical_full_min 0.545
####################################################################### 
# 
# 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_guoshq_0910
_database_code_depnum_ccdc_archive 'CCDC 2073712'
loop_
_audit_author_name
_audit_author_address
'guo suan'
;LanZhou University
China
;
_audit_update_record             
;
2021-03-28 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;
_audit_creation_date             2020-09-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 Cl N O4 S'
_chemical_formula_sum            'C23 H20 Cl N O4 S'
_chemical_formula_weight         441.91
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   12.7213(3)
_cell_length_b                   10.0584(3)
_cell_length_c                   17.2909(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.273(3)
_cell_angle_gamma                90
_cell_volume                     2123.83(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3180
_cell_measurement_temperature    292.4(4)
_cell_measurement_theta_max      69.8100
_cell_measurement_theta_min      9.6830
_shelx_estimated_absorpt_T_max   0.874
_shelx_estimated_absorpt_T_min   0.751
_exptl_absorpt_coefficient_mu    2.765
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7861
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         3.619
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.4(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     87.00 176.00   1.00    1.00    --  108.00  63.00 -30.00   89
  2  ω    135.00 161.00   1.00    1.00    --  108.00  63.00 -60.00   26
  3  ω    101.00 127.00   1.00    1.00    --  108.00  63.00 -60.00   26
  4  ω     92.00 118.00   1.00    1.00    --   54.00  57.00-150.00   26
  5  ω     33.00 112.00   1.00    1.00    --   54.00  57.00-180.00   79
  6  ω     38.00 130.00   1.00    1.00    --  108.00 -50.00-180.00   92
  7  ω     59.00 138.00   1.00    1.00    --  108.00 -91.00-180.00   79
  8  ω     36.00 115.00   1.00    1.00    --  108.00-111.00   0.00   79
  9  ω     99.00 173.00   1.00    1.00    --  108.00 -12.00  90.00   74
 10  ω     37.00 100.00   1.00    1.00    --   54.00-125.00  90.00   63
 11  ω    -12.00  16.00   1.00    1.00    --    0.00 -57.00  60.00   28
 12  ω    -62.00 -37.00   1.00    1.00    --    0.00 -57.00  60.00   25
 13  ω    -17.00  80.00   1.00    1.00    --   54.00 -38.00-120.00   97
 14  ω     29.00  60.00   1.00    1.00    --   54.00 -77.00-180.00   31
 15  ω     36.00 104.00   1.00    1.00    --  108.00-111.00-180.00   68
 16  ω    -20.00   5.00   1.00    1.00    --    0.00  57.00-150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1166793000
_diffrn_orient_matrix_UB_12      0.0496070000
_diffrn_orient_matrix_UB_13      -0.0416672000
_diffrn_orient_matrix_UB_21      0.0424123000
_diffrn_orient_matrix_UB_22      0.1441930000
_diffrn_orient_matrix_UB_23      0.0058870000
_diffrn_orient_matrix_UB_31      0.0221615000
_diffrn_orient_matrix_UB_32      -0.0147092000
_diffrn_orient_matrix_UB_33      -0.0827350000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3133
_reflns_number_total             3741
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0037(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3741
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.048
_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)+(0.0528P)²+0.6113P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1139
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C20(H20), C22(H22), C26(H26), C30(H30)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_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
Cl1 Cl 0.90805(5) 0.08451(9) 0.37720(5) 0.0987(3) Uani 1 1 d . . . . .
S1 S 0.41427(4) 0.06960(6) 0.18652(3) 0.05713(19) Uani 1 1 d . . . . .
O1 O 0.11801(12) 0.02123(19) 0.08657(10) 0.0705(5) Uani 1 1 d . . . . .
O2 O 0.37156(10) 0.03726(17) -0.05106(9) 0.0607(4) Uani 1 1 d . . . . .
O3 O 0.38390(17) 0.19090(17) 0.14325(12) 0.0945(7) Uani 1 1 d . . . . .
O4 O 0.35287(13) 0.0269(2) 0.24021(10) 0.0829(6) Uani 1 1 d . . . . .
N1 N 0.24111(11) 0.01518(16) 0.01404(9) 0.0409(4) Uani 1 1 d . . . . .
C1 C 0.41398(15) -0.0595(2) 0.11685(11) 0.0455(4) Uani 1 1 d . . . . .
H1A H 0.458602 -0.032352 0.082415 0.055 Uiso 1 1 calc R U . . .
H1B H 0.447681 -0.137765 0.146354 0.055 Uiso 1 1 calc R U . . .
C2 C 0.30009(14) -0.09680(19) 0.06391(11) 0.0424(4) Uani 1 1 d . . . . .
H2 H 0.256927 -0.121395 0.100599 0.051 Uiso 1 1 calc R U . . .
C3 C 0.30125(16) -0.21760(19) 0.01177(11) 0.0460(4) Uani 1 1 d . . . . .
C4 C 0.20225(19) -0.2778(2) -0.02567(14) 0.0650(6) Uani 1 1 d . . . . .
H4 H 0.137782 -0.242973 -0.018749 0.078 Uiso 1 1 calc R U . . .
C5 C 0.1981(3) -0.3895(3) -0.07334(17) 0.0874(9) Uani 1 1 d . . . . .
H5 H 0.131136 -0.429548 -0.097756 0.105 Uiso 1 1 calc R U . . .
C6 C 0.2927(3) -0.4410(3) -0.08463(17) 0.0908(10) Uani 1 1 d . . . . .
H6 H 0.289894 -0.515741 -0.116843 0.109 Uiso 1 1 calc R U . . .
C7 C 0.3904(3) -0.3824(3) -0.04848(15) 0.0766(7) Uani 1 1 d . . . . .
H7 H 0.454441 -0.417566 -0.056068 0.092 Uiso 1 1 calc R U . . .
C8 C 0.39580(19) -0.2709(2) -0.00046(13) 0.0569(5) Uani 1 1 d . . . . .
H8 H 0.463190 -0.231621 0.023694 0.068 Uiso 1 1 calc R U . . .
C9 C 0.27738(14) 0.05606(19) -0.05169(11) 0.0420(4) Uani 1 1 d . . . . .
C10 C 0.19602(14) 0.11002(18) -0.12399(10) 0.0405(4) Uani 1 1 d . . . . .
C11 C 0.23041(17) 0.2033(2) -0.17085(12) 0.0507(5) Uani 1 1 d . . . . .
H11 H 0.303002 0.231254 -0.156378 0.061 Uiso 1 1 calc R U . . .
C12 C 0.1571(2) 0.2546(2) -0.23883(13) 0.0616(6) Uani 1 1 d . . . . .
H12 H 0.179879 0.318655 -0.269472 0.074 Uiso 1 1 calc R U . . .
C13 C 0.0500(2) 0.2108(3) -0.26130(13) 0.0649(6) Uani 1 1 d . . . . .
H13 H 0.000378 0.246218 -0.306726 0.078 Uiso 1 1 calc R U . . .
C14 C 0.01647(17) 0.1149(2) -0.21674(12) 0.0584(5) Uani 1 1 d . . . . .
H14 H -0.055231 0.083792 -0.233071 0.070 Uiso 1 1 calc R U . . .
C15 C 0.08856(15) 0.0645(2) -0.14799(11) 0.0469(4) Uani 1 1 d . . . . .
H15 H 0.065379 0.000255 -0.117728 0.056 Uiso 1 1 calc R U . . .
C16 C 0.15797(14) 0.0776(2) 0.04024(11) 0.0486(5) Uani 1 1 d . . . . .
C17 C 0.12749(19) 0.2179(2) 0.01586(14) 0.0647(6) Uani 1 1 d . . . . .
H17A H 0.183224 0.257310 -0.004401 0.097 Uiso 1 1 calc R U . . .
H17B H 0.120741 0.267417 0.061700 0.097 Uiso 1 1 calc R U . . .
H17C H 0.058903 0.219273 -0.025402 0.097 Uiso 1 1 calc R U . . .
C18 C 0.77039(18) 0.0836(2) 0.32462(14) 0.0598(6) Uani 1 1 d . . . . .
C19 C 0.55382(17) 0.07819(19) 0.24124(11) 0.0483(5) Uani 1 1 d . . . . .
C20 C 0.59094(18) 0.0008(2) 0.30840(13) 0.0628(6) Uani 1 1 d . . . . .
H20 H 0.542709 -0.053218 0.325752 0.075 Uiso 1 1 calc R U . . .
C22 C 0.6245(2) 0.1596(3) 0.21619(15) 0.0765(7) Uani 1 1 d . . . . .
H22 H 0.598678 0.212758 0.170811 0.092 Uiso 1 1 calc R U . . .
C26 C 0.7333(2) 0.1623(3) 0.25827(17) 0.0799(8) Uani 1 1 d . . . . .
H26 H 0.781473 0.217503 0.241677 0.096 Uiso 1 1 calc R U . . .
C30 C 0.7004(2) 0.0036(3) 0.35009(15) 0.0722(7) Uani 1 1 d . . . . .
H30 H 0.726459 -0.049198 0.395609 0.087 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C18 1.732(2) . ?
S1 O3 1.4267(18) . ?
S1 O4 1.4361(18) . ?
S1 C1 1.7706(19) . ?
S1 C19 1.764(2) . ?
O1 C16 1.204(2) . ?
O2 C9 1.210(2) . ?
N1 C2 1.488(2) . ?
N1 C9 1.403(2) . ?
N1 C16 1.410(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.528(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.516(3) . ?
C3 C4 1.384(3) . ?
C3 C8 1.386(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.374(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.360(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.386(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.484(3) . ?
C10 C11 1.388(3) . ?
C10 C15 1.390(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.493(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C26 1.365(4) . ?
C18 C30 1.362(3) . ?
C19 C20 1.368(3) . ?
C19 C22 1.373(3) . ?
C20 H20 0.9300 . ?
C20 C30 1.377(3) . ?
C22 H22 0.9300 . ?
C22 C26 1.371(4) . ?
C26 H26 0.9300 . ?
C30 H30 0.9300 . ?

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
O3 S1 O4 118.56(13) . . ?
O3 S1 C1 108.77(11) . . ?
O3 S1 C19 108.86(11) . . ?
O4 S1 C1 108.83(11) . . ?
O4 S1 C19 108.40(10) . . ?
C19 S1 C1 102.16(9) . . ?
C9 N1 C2 117.69(14) . . ?
C9 N1 C16 125.23(16) . . ?
C16 N1 C2 116.93(14) . . ?
S1 C1 H1A 108.7 . . ?
S1 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C2 C1 S1 114.11(13) . . ?
C2 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
N1 C2 C1 113.65(15) . . ?
N1 C2 H2 106.5 . . ?
N1 C2 C3 110.47(14) . . ?
C1 C2 H2 106.5 . . ?
C3 C2 C1 112.80(15) . . ?
C3 C2 H2 106.5 . . ?
C4 C3 C2 118.03(19) . . ?
C4 C3 C8 118.3(2) . . ?
C8 C3 C2 123.67(18) . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.7(3) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.7(3) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.8(3) . . ?
C8 C7 H7 119.6 . . ?
C3 C8 H8 119.8 . . ?
C7 C8 C3 120.4(2) . . ?
C7 C8 H8 119.8 . . ?
O2 C9 N1 119.78(17) . . ?
O2 C9 C10 121.31(16) . . ?
N1 C9 C10 118.65(15) . . ?
C11 C10 C9 118.64(16) . . ?
C11 C10 C15 119.52(18) . . ?
C15 C10 C9 121.75(16) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.14(19) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.9(2) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.3(2) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 120.1 . . ?
C14 C15 C10 119.84(18) . . ?
C14 C15 H15 120.1 . . ?
O1 C16 N1 119.92(19) . . ?
O1 C16 C17 120.56(18) . . ?
N1 C16 C17 119.29(18) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C26 C18 Cl1 119.93(19) . . ?
C30 C18 Cl1 119.3(2) . . ?
C30 C18 C26 120.7(2) . . ?
C20 C19 S1 118.93(16) . . ?
C20 C19 C22 120.4(2) . . ?
C22 C19 S1 120.63(17) . . ?
C19 C20 H20 120.3 . . ?
C19 C20 C30 119.4(2) . . ?
C30 C20 H20 120.3 . . ?
C19 C22 H22 120.1 . . ?
C26 C22 C19 119.8(2) . . ?
C26 C22 H22 120.1 . . ?
C18 C26 C22 119.6(2) . . ?
C18 C26 H26 120.2 . . ?
C22 C26 H26 120.2 . . ?
C18 C30 C20 120.0(2) . . ?
C18 C30 H30 120.0 . . ?
C20 C30 H30 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C18 C26 C22 179.0(2) . . . . ?
Cl1 C18 C30 C20 -179.3(2) . . . . ?
S1 C1 C2 N1 59.82(18) . . . . ?
S1 C1 C2 C3 -173.44(13) . . . . ?
S1 C19 C20 C30 178.0(2) . . . . ?
S1 C19 C22 C26 -178.3(2) . . . . ?
O2 C9 C10 C11 -35.4(3) . . . . ?
O2 C9 C10 C15 141.2(2) . . . . ?
O3 S1 C1 C2 -69.14(17) . . . . ?
O3 S1 C19 C20 155.56(19) . . . . ?
O3 S1 C19 C22 -25.5(2) . . . . ?
O4 S1 C1 C2 61.36(16) . . . . ?
O4 S1 C19 C20 25.3(2) . . . . ?
O4 S1 C19 C22 -155.7(2) . . . . ?
N1 C2 C3 C4 -65.0(2) . . . . ?
N1 C2 C3 C8 114.95(19) . . . . ?
N1 C9 C10 C11 150.49(18) . . . . ?
N1 C9 C10 C15 -32.9(3) . . . . ?
C1 S1 C19 C20 -89.51(19) . . . . ?
C1 S1 C19 C22 89.5(2) . . . . ?
C1 C2 C3 C4 166.56(17) . . . . ?
C1 C2 C3 C8 -13.5(3) . . . . ?
C2 N1 C9 O2 -25.9(3) . . . . ?
C2 N1 C9 C10 148.38(16) . . . . ?
C2 N1 C16 O1 -19.2(3) . . . . ?
C2 N1 C16 C17 155.39(18) . . . . ?
C2 C3 C4 C5 -179.3(2) . . . . ?
C2 C3 C8 C7 179.44(19) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C3 C8 C7 -0.6(3) . . . . ?
C4 C5 C6 C7 0.3(4) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C6 C7 C8 C3 0.3(4) . . . . ?
C8 C3 C4 C5 0.8(3) . . . . ?
C9 N1 C2 C1 72.4(2) . . . . ?
C9 N1 C2 C3 -55.5(2) . . . . ?
C9 N1 C16 O1 165.49(19) . . . . ?
C9 N1 C16 C17 -19.9(3) . . . . ?
C9 C10 C11 C12 179.44(19) . . . . ?
C9 C10 C15 C14 -178.27(19) . . . . ?
C10 C11 C12 C13 -1.5(3) . . . . ?
C11 C10 C15 C14 -1.7(3) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
C12 C13 C14 C15 1.9(4) . . . . ?
C13 C14 C15 C10 -0.6(3) . . . . ?
C15 C10 C11 C12 2.8(3) . . . . ?
C16 N1 C2 C1 -103.26(18) . . . . ?
C16 N1 C2 C3 128.79(17) . . . . ?
C16 N1 C9 O2 149.4(2) . . . . ?
C16 N1 C9 C10 -36.3(3) . . . . ?
C19 S1 C1 C2 175.87(14) . . . . ?
C19 C20 C30 C18 0.5(4) . . . . ?
C19 C22 C26 C18 0.2(4) . . . . ?
C20 C19 C22 C26 0.7(4) . . . . ?
C22 C19 C20 C30 -1.0(4) . . . . ?
C26 C18 C30 C20 0.5(4) . . . . ?
C30 C18 C26 C22 -0.8(4) . . . . ?

_olex2_date_sample_data_collection 2020-09-10
_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 1.240
_oxdiff_exptl_absorpt_empirical_full_min 0.779
####################################################################### 
# 
# 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_guoshq_1229
_database_code_depnum_ccdc_archive 'CCDC 2073716'
loop_
_audit_author_name
_audit_author_address
'guo bmesuan'
;LanZhou University
China
;
_audit_update_record             
;
2021-03-28 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;
_audit_creation_date             2020-12-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H25 N O4 S'
_chemical_formula_sum            'C25 H25 N O4 S'
_chemical_formula_weight         435.52
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   19.8661(3)
_cell_length_b                   9.09317(15)
_cell_length_c                   25.7813(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.6714(18)
_cell_angle_gamma                90
_cell_volume                     4385.48(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8979
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      75.5340
_cell_measurement_theta_min      3.6380
_shelx_estimated_absorpt_T_max   0.898
_shelx_estimated_absorpt_T_min   0.810
_exptl_absorpt_coefficient_mu    1.573
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.07487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            13779
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.911
_diffrn_reflns_theta_min         3.641
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  21.00   1.00    0.10    --   43.05 -19.00 -60.00   35
  2  ω    -26.00   7.00   1.00    0.10    --   43.05 -37.00 -60.00   33
  3  ω     -2.00  76.00   1.00    0.10    --   43.05-103.00  58.00   78
  4  ω     63.00 107.00   1.00    0.10    --  109.26-103.00  58.00   44
  5  ω     77.00 102.00   1.00    0.10    --  109.26 -77.00  90.00   25
  6  ω     37.00  67.00   1.00    0.10    --  109.26 -61.00 120.00   30
  7  ω     40.00  68.00   1.00    0.10    --  109.26 -77.00  90.00   28
  8  ω     35.00  60.00   1.00    0.10    --  109.26 -61.00  60.00   25
  9  ω     36.00  64.00   1.00    0.10    --  109.26 -61.00 -60.00   28
 10  ω     35.00  68.00   1.00    0.10    --  109.26 -61.00-120.00   33
 11  ω     37.00  63.00   1.00    0.10    --  109.26 -61.00 -90.00   26
 12  ω     42.00  68.00   1.00    0.10    --  109.26 -61.00-150.00   26
 13  ω     35.00  66.00   1.00    0.10    --  109.26 -61.00-180.00   31
 14  ω     26.00 112.00   1.00    0.10    --   43.05  57.00-120.00   86
 15  ω     87.00 166.00   1.00    0.10    --  109.26 103.00 160.00   79
 16  ω    -49.00 -24.00   1.00    0.10    -- -100.00  45.00 150.00   25
 17  ω    -52.00 -25.00   1.00    0.10    -- -100.00  45.00  90.00   27
 18  ω    -50.00 -25.00   1.00    0.10    -- -100.00  45.00  30.00   25
 19  ω    -50.00 -24.00   1.00    0.10    -- -100.00  45.00 -30.00   26
 20  ω    -54.00 -29.00   1.00    0.10    -- -100.00  45.00   0.00   25
 21  ω    -67.00 -39.00   1.00    0.10    -- -100.00  61.00 -60.00   28
 22  ω    -54.00 -27.00   1.00    0.10    -- -100.00  45.00 -90.00   27
 23  ω    -73.00 -44.00   1.00    0.10    -- -100.00  61.00   0.00   29
 24  ω    -73.00 -33.00   1.00    0.10    -- -100.00  61.00 120.00   40
 25  ω    -74.00 -49.00   1.00    0.10    -- -100.00  61.00 150.00   25
 26  ω    -70.00  -3.00   1.00    0.10    --  -43.05 103.00 160.00   67
 27  ω   -106.00 -51.00   1.00    0.10    -- -100.00 103.00 160.00   55
 28  ω   -149.00 -90.00   1.00    0.10    -- -100.00 -94.00  90.00   59
 29  ω   -152.00-108.00   1.00    0.10    -- -100.00-103.00  58.00   44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0289302000
_diffrn_orient_matrix_UB_12      -0.0556424000
_diffrn_orient_matrix_UB_13      0.0599084000
_diffrn_orient_matrix_UB_21      -0.0121411000
_diffrn_orient_matrix_UB_22      0.1533416000
_diffrn_orient_matrix_UB_23      0.0206439000
_diffrn_orient_matrix_UB_31      -0.0761133000
_diffrn_orient_matrix_UB_32      -0.0457305000
_diffrn_orient_matrix_UB_33      -0.0035850000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3926
_reflns_number_total             4342
_reflns_odcompleteness_completeness 99.83
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4342
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.063
_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)+(0.0776P)²+1.9746P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1279
_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 Ternary CH refined with riding coordinates:
 C10(H10), C17(H17)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C20(H20), C21(H21), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C18(H18A,H18B,H18C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.52182(2) 1.05650(5) 0.67961(2) 0.03583(14) Uani 1 1 d . . . . .
O1 O 0.43231(6) 0.58674(13) 0.61018(5) 0.0376(3) Uani 1 1 d . . . . .
O2 O 0.41758(6) 0.97620(13) 0.49780(5) 0.0352(3) Uani 1 1 d . . . . .
O3 O 0.59421(6) 1.04502(17) 0.71688(6) 0.0504(4) Uani 1 1 d . . . . .
O4 O 0.50440(8) 1.17095(15) 0.63845(5) 0.0490(3) Uani 1 1 d . . . . .
N1 N 0.41600(6) 0.78524(14) 0.55396(5) 0.0282(3) Uani 1 1 d . . . . .
C1 C 0.36643(7) 0.53999(16) 0.51688(6) 0.0266(3) Uani 1 1 d . . . . .
C2 C 0.37885(8) 0.38964(18) 0.52142(6) 0.0311(3) Uani 1 1 d . . . . .
H2 H 0.414654 0.351932 0.551902 0.037 Uiso 1 1 calc R U . . .
C3 C 0.33815(9) 0.29566(19) 0.48077(7) 0.0386(4) Uani 1 1 d . . . . .
H3 H 0.347190 0.195095 0.483505 0.046 Uiso 1 1 calc R U . . .
C4 C 0.28367(9) 0.3519(2) 0.43578(7) 0.0394(4) Uani 1 1 d . . . . .
H4 H 0.256162 0.288712 0.408504 0.047 Uiso 1 1 calc R U . . .
C5 C 0.27025(8) 0.5006(2) 0.43140(7) 0.0347(4) Uani 1 1 d . . . . .
H5 H 0.233453 0.537541 0.401381 0.042 Uiso 1 1 calc R U . . .
C6 C 0.31159(8) 0.59577(18) 0.47175(6) 0.0298(3) Uani 1 1 d . . . . .
H6 H 0.302708 0.696377 0.468681 0.036 Uiso 1 1 calc R U . . .
C7 C 0.40880(7) 0.63481(17) 0.56350(6) 0.0286(3) Uani 1 1 d . . . . .
C8 C 0.42485(7) 0.84548(18) 0.50636(6) 0.0284(3) Uani 1 1 d . . . . .
C9 C 0.44944(9) 0.7483(2) 0.46918(7) 0.0375(4) Uani 1 1 d . . . . .
H9A H 0.410584 0.732066 0.435466 0.056 Uiso 1 1 calc R U . . .
H9B H 0.465236 0.655768 0.487068 0.056 Uiso 1 1 calc R U . . .
H9C H 0.488232 0.794913 0.461245 0.056 Uiso 1 1 calc R U . . .
C10 C 0.42299(8) 0.88874(17) 0.60043(6) 0.0277(3) Uani 1 1 d . . . . .
H10 H 0.418811 0.987652 0.584561 0.033 Uiso 1 1 calc R U . . .
C11 C 0.35998(7) 0.87243(17) 0.62113(6) 0.0273(3) Uani 1 1 d . . . . .
C12 C 0.36143(8) 0.78934(17) 0.66668(6) 0.0299(3) Uani 1 1 d . . . . .
H12 H 0.402480 0.736930 0.685844 0.036 Uiso 1 1 calc R U . . .
C13 C 0.30241(8) 0.78342(19) 0.68403(7) 0.0342(3) Uani 1 1 d . . . . .
H13 H 0.304375 0.728338 0.714900 0.041 Uiso 1 1 calc R U . . .
C14 C 0.24032(8) 0.8599(2) 0.65525(7) 0.0370(4) Uani 1 1 d . . . . .
H14 H 0.200729 0.855996 0.666745 0.044 Uiso 1 1 calc R U . . .
C15 C 0.23798(8) 0.94163(19) 0.60944(7) 0.0360(4) Uani 1 1 d . . . . .
H15 H 0.196545 0.992455 0.589958 0.043 Uiso 1 1 calc R U . . .
C16 C 0.29711(8) 0.94820(18) 0.59240(6) 0.0314(3) Uani 1 1 d . . . . .
H16 H 0.294977 1.003538 0.561549 0.038 Uiso 1 1 calc R U . . .
C17 C 0.49911(8) 0.88093(18) 0.64453(6) 0.0300(3) Uani 1 1 d . . . . .
H17 H 0.499974 0.804250 0.671460 0.036 Uiso 1 1 calc R U . . .
C18 C 0.55758(8) 0.8496(2) 0.61953(7) 0.0370(4) Uani 1 1 d . . . . .
H18A H 0.552411 0.915867 0.589437 0.056 Uiso 1 1 calc R U . . .
H18B H 0.553255 0.750116 0.606371 0.056 Uiso 1 1 calc R U . . .
H18C H 0.603678 0.863290 0.647117 0.056 Uiso 1 1 calc R U . . .
C19 C 0.46508(8) 1.07376(18) 0.71877(6) 0.0312(3) Uani 1 1 d . . . . .
C20 C 0.47960(8) 0.99388(19) 0.76722(6) 0.0338(3) Uani 1 1 d . . . . .
H20 H 0.522011 0.941157 0.781134 0.041 Uiso 1 1 calc R U . . .
C21 C 0.43076(9) 0.9933(2) 0.79453(7) 0.0377(4) Uani 1 1 d . . . . .
H21 H 0.440372 0.939447 0.826882 0.045 Uiso 1 1 calc R U . . .
C22 C 0.36723(9) 1.0722(2) 0.77435(8) 0.0408(4) Uani 1 1 d . . . . .
C23 C 0.35539(9) 1.1570(2) 0.72724(8) 0.0439(4) Uani 1 1 d . . . . .
H23 H 0.314324 1.214321 0.714555 0.053 Uiso 1 1 calc R U . . .
C24 C 0.40316(9) 1.15792(19) 0.69886(7) 0.0381(4) Uani 1 1 d . . . . .
H24 H 0.394161 1.213767 0.667016 0.046 Uiso 1 1 calc R U . . .
C25 C 0.31202(12) 1.0639(3) 0.80246(11) 0.0609(6) Uani 1 1 d . . . . .
H25A H 0.327457 0.995210 0.832441 0.091 Uiso 1 1 calc R U . . .
H25B H 0.267293 1.031821 0.776525 0.091 Uiso 1 1 calc R U . . .
H25C H 0.306141 1.159220 0.816330 0.091 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4394(13) . ?
S1 O4 1.4429(14) . ?
S1 C17 1.8153(17) . ?
S1 C19 1.7553(16) . ?
O1 C7 1.2162(19) . ?
O2 C8 1.209(2) . ?
N1 C7 1.406(2) . ?
N1 C8 1.4079(19) . ?
N1 C10 1.4930(19) . ?
C1 C2 1.387(2) . ?
C1 C6 1.394(2) . ?
C1 C7 1.488(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(2) . ?
C6 H6 0.9300 . ?
C8 C9 1.501(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9800 . ?
C10 C11 1.524(2) . ?
C10 C17 1.5579(19) . ?
C11 C12 1.388(2) . ?
C11 C16 1.400(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.390(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.393(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.387(2) . ?
C16 H16 0.9300 . ?
C17 H17 0.9800 . ?
C17 C18 1.533(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.389(2) . ?
C19 C24 1.392(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.377(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.392(3) . ?
C22 C23 1.390(3) . ?
C22 C25 1.506(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.380(3) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
O3 S1 O4 118.79(9) . . ?
O3 S1 C17 107.08(8) . . ?
O3 S1 C19 108.26(8) . . ?
O4 S1 C17 108.06(7) . . ?
O4 S1 C19 108.49(8) . . ?
C19 S1 C17 105.38(7) . . ?
C7 N1 C8 125.53(13) . . ?
C7 N1 C10 117.42(12) . . ?
C8 N1 C10 116.69(12) . . ?
C2 C1 C6 119.71(14) . . ?
C2 C1 C7 117.81(13) . . ?
C6 C1 C7 122.26(14) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.21(15) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.81(16) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.35(16) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.08(15) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.82(15) . . ?
C5 C6 H6 120.1 . . ?
O1 C7 N1 119.68(14) . . ?
O1 C7 C1 121.02(14) . . ?
N1 C7 C1 119.05(13) . . ?
O2 C8 N1 119.96(14) . . ?
O2 C8 C9 120.46(14) . . ?
N1 C8 C9 119.37(14) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 H10 105.8 . . ?
N1 C10 C11 110.75(12) . . ?
N1 C10 C17 111.23(12) . . ?
C11 C10 H10 105.8 . . ?
C11 C10 C17 116.74(12) . . ?
C17 C10 H10 105.8 . . ?
C12 C11 C10 124.28(13) . . ?
C12 C11 C16 118.44(14) . . ?
C16 C11 C10 117.27(14) . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 120.91(14) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.07(15) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.52(15) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.32(15) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.73(15) . . ?
C15 C16 H16 119.6 . . ?
S1 C17 H17 109.3 . . ?
C10 C17 S1 109.93(11) . . ?
C10 C17 H17 109.3 . . ?
C18 C17 S1 106.04(11) . . ?
C18 C17 C10 112.85(12) . . ?
C18 C17 H17 109.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 S1 119.43(12) . . ?
C20 C19 C24 120.64(16) . . ?
C24 C19 S1 119.73(13) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.53(15) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 119.6 . . ?
C20 C21 C22 120.88(17) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C25 120.65(19) . . ?
C23 C22 C21 118.55(17) . . ?
C23 C22 C25 120.80(18) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 C22 121.51(16) . . ?
C24 C23 H23 119.2 . . ?
C19 C24 H24 120.6 . . ?
C23 C24 C19 118.76(16) . . ?
C23 C24 H24 120.6 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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 C19 C20 C21 -172.21(13) . . . . ?
S1 C19 C24 C23 172.92(13) . . . . ?
O3 S1 C17 C10 -176.12(10) . . . . ?
O3 S1 C17 C18 -53.84(13) . . . . ?
O3 S1 C19 C20 -38.12(15) . . . . ?
O3 S1 C19 C24 146.93(13) . . . . ?
O4 S1 C17 C10 -47.06(12) . . . . ?
O4 S1 C17 C18 75.23(12) . . . . ?
O4 S1 C19 C20 -168.29(12) . . . . ?
O4 S1 C19 C24 16.76(15) . . . . ?
N1 C10 C11 C12 97.89(16) . . . . ?
N1 C10 C11 C16 -82.95(17) . . . . ?
N1 C10 C17 S1 151.65(10) . . . . ?
N1 C10 C17 C18 33.49(18) . . . . ?
C1 C2 C3 C4 -1.3(2) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C2 C1 C7 O1 -26.9(2) . . . . ?
C2 C1 C7 N1 158.96(13) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C6 C1 C2 C3 1.5(2) . . . . ?
C6 C1 C7 O1 147.78(15) . . . . ?
C6 C1 C7 N1 -26.4(2) . . . . ?
C7 N1 C8 O2 166.57(13) . . . . ?
C7 N1 C8 C9 -18.7(2) . . . . ?
C7 N1 C10 C11 -56.09(16) . . . . ?
C7 N1 C10 C17 75.45(16) . . . . ?
C7 C1 C2 C3 176.28(14) . . . . ?
C7 C1 C6 C5 -175.18(14) . . . . ?
C8 N1 C7 O1 147.40(15) . . . . ?
C8 N1 C7 C1 -38.3(2) . . . . ?
C8 N1 C10 C11 130.45(13) . . . . ?
C8 N1 C10 C17 -98.00(14) . . . . ?
C10 N1 C7 O1 -25.4(2) . . . . ?
C10 N1 C7 C1 148.86(13) . . . . ?
C10 N1 C8 O2 -20.58(19) . . . . ?
C10 N1 C8 C9 154.19(13) . . . . ?
C10 C11 C12 C13 178.02(14) . . . . ?
C10 C11 C16 C15 -178.51(14) . . . . ?
C11 C10 C17 S1 -79.95(15) . . . . ?
C11 C10 C17 C18 161.89(14) . . . . ?
C11 C12 C13 C14 0.8(2) . . . . ?
C12 C11 C16 C15 0.7(2) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C14 C15 C16 C11 0.0(2) . . . . ?
C16 C11 C12 C13 -1.1(2) . . . . ?
C17 S1 C19 C20 76.18(14) . . . . ?
C17 S1 C19 C24 -98.77(14) . . . . ?
C17 C10 C11 C12 -30.7(2) . . . . ?
C17 C10 C11 C16 148.42(14) . . . . ?
C19 S1 C17 C10 68.77(12) . . . . ?
C19 S1 C17 C18 -168.95(11) . . . . ?
C19 C20 C21 C22 -0.3(3) . . . . ?
C20 C19 C24 C23 -2.0(2) . . . . ?
C20 C21 C22 C23 -2.7(3) . . . . ?
C20 C21 C22 C25 176.27(17) . . . . ?
C21 C22 C23 C24 3.5(3) . . . . ?
C22 C23 C24 C19 -1.2(3) . . . . ?
C24 C19 C20 C21 2.7(2) . . . . ?
C25 C22 C23 C24 -175.52(18) . . . . ?

_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 9.271
_oxdiff_exptl_absorpt_empirical_full_min 0.440
####################################################################### 
# 
# 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_guoshq_0603
_database_code_depnum_ccdc_archive 'CCDC 2073707'
loop_
_audit_author_name
_audit_author_address
guo
;LanZhou University
China
;
_audit_update_record             
;
2021-03-28 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;
_audit_creation_date             2020-06-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H22 N4 O2 S'
_chemical_formula_sum            'C23 H22 N4 O2 S'
_chemical_formula_weight         418.50
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.65981(14)
_cell_length_b                   17.7339(2)
_cell_length_c                   27.7046(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4254.66(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3580
_cell_measurement_temperature    293.41(10)
_cell_measurement_theta_max      69.6750
_cell_measurement_theta_min      8.0040
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.570
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9603
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         4.988
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.41(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_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    -20.00  18.00   1.00    1.00    --    0.00 -57.00   0.00   38
  2  ω     23.00 111.00   1.00    1.00    --   54.00-125.00   0.00   88
  3  ω     39.00 105.00   1.00    2.00    --  108.00-111.00 -60.00   66
  4  ω     41.00  71.00   1.00    2.00    --  108.00-111.00 120.00   30
  5  ω     55.00 113.00   1.00    2.00    --  108.00-111.00 150.00   58
  6  ω     76.00 150.00   1.00    2.00    --  108.00  25.00  60.00   74
  7  ω     66.00 125.00   1.00    1.00    --   54.00  38.00 -60.00   59
  8  ω     39.00 107.00   1.00    1.00    --   54.00  57.00-120.00   68
  9  ω     66.00 133.00   1.00    2.00    --  108.00 178.00  60.00   67
 10  ω    -66.00 -23.00   1.00    1.00    --    0.00 -57.00   0.00   43
 11  ω    -68.00 -42.00   1.00    1.00    --    0.00 169.00  81.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0511451000
_diffrn_orient_matrix_UB_12      0.0398865000
_diffrn_orient_matrix_UB_13      -0.0467508000
_diffrn_orient_matrix_UB_21      0.1678643000
_diffrn_orient_matrix_UB_22      0.0013109000
_diffrn_orient_matrix_UB_23      0.0183982000
_diffrn_orient_matrix_UB_31      0.0293374000
_diffrn_orient_matrix_UB_32      -0.0771461000
_diffrn_orient_matrix_UB_33      -0.0238379000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3091
_reflns_number_total             3766
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.00149(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3766
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.037
_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)+(0.0554P)²+1.0068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1142
_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 Ternary CH refined with riding coordinates:
 C11(H11), C20(H20)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C10(H10), C13(H13), C17(H17), C19(H19), C21(H21), C22(H22), C23(H23),
 C24(H24), C25(H25), C26(H26), C27(H27), C29(H29), C30(H30)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C28(H28A,H28B,H28C)
;
_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 0.11114(7) 0.16542(3) 0.51834(2) 0.05565(18) Uani 1 1 d . . . . .
N2 N 0.06786(17) 0.10973(7) 0.63103(5) 0.0382(3) Uani 1 1 d . . . . .
N3 N 0.15763(17) -0.00093(7) 0.66020(5) 0.0381(3) Uani 1 1 d . . . . .
C4 C 0.3747(2) 0.09090(10) 0.68059(7) 0.0479(5) Uani 1 1 d . . . . .
H4 H 0.328185 0.135672 0.670907 0.057 Uiso 1 1 calc R U . . .
C5 C 0.3698(2) -0.04510(10) 0.69165(6) 0.0453(4) Uani 1 1 d . . . . .
C6 C 0.0387(2) 0.04058(9) 0.63733(6) 0.0395(4) Uani 1 1 d . . . . .
C7 C -0.1386(2) 0.20337(9) 0.64258(7) 0.0407(4) Uani 1 1 d . . . . .
C8 C 0.2996(2) 0.02179(9) 0.67662(6) 0.0374(4) Uani 1 1 d . . . . .
N9 N 0.1433(2) -0.07797(8) 0.66563(6) 0.0518(4) Uani 1 1 d . . . . .
C10 C -0.0994(2) 0.20943(11) 0.69085(7) 0.0484(5) Uani 1 1 d . . . . .
H10 H -0.012415 0.184574 0.702463 0.058 Uiso 1 1 calc R U . . .
C11 C -0.0442(2) 0.15774(9) 0.60649(6) 0.0400(4) Uani 1 1 d . . . . .
H11 H -0.113973 0.126091 0.587393 0.048 Uiso 1 1 calc R U . . .
N12 N 0.2686(2) -0.10381(8) 0.68434(7) 0.0569(5) Uani 1 1 d . . . . .
C13 C -0.2693(2) 0.24078(10) 0.62633(8) 0.0533(5) Uani 1 1 d . . . . .
H13 H -0.297901 0.236964 0.594067 0.064 Uiso 1 1 calc R U . . .
O14 O 0.1793(3) 0.22342(10) 0.48892(6) 0.0895(6) Uani 1 1 d . . . . .
C15 C 0.2590(2) 0.10218(11) 0.53450(7) 0.0474(4) Uani 1 1 d . . . . .
O16 O -0.0151(2) 0.12259(11) 0.49907(6) 0.0805(5) Uani 1 1 d . . . . .
C17 C -0.1889(3) 0.25231(12) 0.72209(8) 0.0586(5) Uani 1 1 d . . . . .
H17 H -0.161828 0.255755 0.754500 0.070 Uiso 1 1 calc R U . . .
C18 C 0.1695(3) 0.25767(11) 0.59624(8) 0.0625(6) Uani 1 1 d . . . . .
H18A H 0.246372 0.224417 0.609292 0.094 Uiso 1 1 calc R U . . .
H18B H 0.125918 0.287467 0.621759 0.094 Uiso 1 1 calc R U . . .
H18C H 0.216199 0.290278 0.572746 0.094 Uiso 1 1 calc R U . . .
C19 C 0.2250(3) 0.02631(11) 0.53815(7) 0.0564(5) Uani 1 1 d . . . . .
H19 H 0.126368 0.008619 0.531249 0.068 Uiso 1 1 calc R U . . .
C20 C 0.0433(3) 0.21164(9) 0.57244(7) 0.0474(5) Uani 1 1 d . . . . .
H20 H -0.033723 0.248383 0.561522 0.057 Uiso 1 1 calc R U . . .
C21 C 0.5188(3) -0.04506(13) 0.71076(8) 0.0614(6) Uani 1 1 d . . . . .
H21 H 0.565827 -0.089497 0.720828 0.074 Uiso 1 1 calc R U . . .
C22 C -0.3575(3) 0.28369(12) 0.65758(10) 0.0631(6) Uani 1 1 d . . . . .
H22 H -0.444641 0.308642 0.646175 0.076 Uiso 1 1 calc R U . . .
C23 C 0.5207(3) 0.08946(13) 0.69951(8) 0.0606(6) Uani 1 1 d . . . . .
H23 H 0.574080 0.134677 0.702775 0.073 Uiso 1 1 calc R U . . .
C24 C 0.4062(3) 0.12819(14) 0.54330(9) 0.0637(6) Uani 1 1 d . . . . .
H24 H 0.429438 0.179108 0.539868 0.076 Uiso 1 1 calc R U . . .
C25 C -0.3170(3) 0.28966(11) 0.70541(9) 0.0619(6) Uani 1 1 d . . . . .
H25 H -0.376135 0.318803 0.726330 0.074 Uiso 1 1 calc R U . . .
C26 C 0.5928(3) 0.02259(14) 0.71415(8) 0.0644(6) Uani 1 1 d . . . . .
H26 H 0.692729 0.024348 0.726366 0.077 Uiso 1 1 calc R U . . .
C27 C 0.3406(4) -0.02289(14) 0.55227(9) 0.0731(7) Uani 1 1 d . . . . .
H27 H 0.319493 -0.074149 0.554913 0.088 Uiso 1 1 calc R U . . .
C28 C -0.0999(3) -0.00461(12) 0.62300(11) 0.0705(7) Uani 1 1 d . . . . .
H28A H -0.186611 0.028422 0.618731 0.106 Uiso 1 1 calc R U . . .
H28B H -0.122789 -0.040728 0.647794 0.106 Uiso 1 1 calc R U . . .
H28C H -0.079042 -0.030518 0.593276 0.106 Uiso 1 1 calc R U . . .
C29 C 0.5190(3) 0.07745(18) 0.55732(10) 0.0832(8) Uani 1 1 d . . . . .
H29 H 0.618895 0.094245 0.563376 0.100 Uiso 1 1 calc R U . . .
C30 C 0.4841(4) 0.00305(17) 0.56228(10) 0.0830(8) Uani 1 1 d . . . . .
H30 H 0.559842 -0.030414 0.572667 0.100 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O14 1.4390(18) . ?
S1 C15 1.760(2) . ?
S1 O16 1.4343(19) . ?
S1 C20 1.8067(19) . ?
N2 C6 1.264(2) . ?
N2 C11 1.459(2) . ?
N3 C6 1.416(2) . ?
N3 C8 1.372(2) . ?
N3 N9 1.3801(18) . ?
C4 H4 0.9300 . ?
C4 C8 1.392(2) . ?
C4 C23 1.369(3) . ?
C5 C8 1.396(2) . ?
C5 N12 1.376(3) . ?
C5 C21 1.394(3) . ?
C6 C28 1.497(3) . ?
C7 C10 1.384(3) . ?
C7 C11 1.524(2) . ?
C7 C13 1.387(3) . ?
N9 N12 1.287(2) . ?
C10 H10 0.9300 . ?
C10 C17 1.389(3) . ?
C11 H11 0.9800 . ?
C11 C20 1.542(3) . ?
C13 H13 0.9300 . ?
C13 C22 1.383(3) . ?
C15 C19 1.381(3) . ?
C15 C24 1.377(3) . ?
C17 H17 0.9300 . ?
C17 C25 1.373(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C18 C20 1.515(3) . ?
C19 H19 0.9300 . ?
C19 C27 1.384(3) . ?
C20 H20 0.9800 . ?
C21 H21 0.9300 . ?
C21 C26 1.363(3) . ?
C22 H22 0.9300 . ?
C22 C25 1.375(3) . ?
C23 H23 0.9300 . ?
C23 C26 1.400(3) . ?
C24 H24 0.9300 . ?
C24 C29 1.384(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C27 C30 1.354(4) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29 0.9300 . ?
C29 C30 1.360(4) . ?
C30 H30 0.9300 . ?

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
O14 S1 C15 107.51(12) . . ?
O14 S1 C20 106.21(10) . . ?
C15 S1 C20 108.34(9) . . ?
O16 S1 O14 118.73(13) . . ?
O16 S1 C15 108.17(11) . . ?
O16 S1 C20 107.52(11) . . ?
C6 N2 C11 119.84(16) . . ?
C8 N3 C6 130.38(13) . . ?
C8 N3 N9 109.58(14) . . ?
N9 N3 C6 119.89(15) . . ?
C8 C4 H4 121.8 . . ?
C23 C4 H4 121.8 . . ?
C23 C4 C8 116.45(19) . . ?
N12 C5 C8 108.78(17) . . ?
N12 C5 C21 130.20(18) . . ?
C21 C5 C8 121.02(19) . . ?
N2 C6 N3 114.89(16) . . ?
N2 C6 C28 130.02(17) . . ?
N3 C6 C28 115.06(15) . . ?
C10 C7 C11 122.93(16) . . ?
C10 C7 C13 118.46(18) . . ?
C13 C7 C11 118.61(17) . . ?
N3 C8 C4 134.73(16) . . ?
N3 C8 C5 103.85(15) . . ?
C4 C8 C5 121.41(18) . . ?
N12 N9 N3 108.70(16) . . ?
C7 C10 H10 119.7 . . ?
C7 C10 C17 120.53(19) . . ?
C17 C10 H10 119.7 . . ?
N2 C11 C7 111.16(14) . . ?
N2 C11 H11 109.1 . . ?
N2 C11 C20 108.68(15) . . ?
C7 C11 H11 109.1 . . ?
C7 C11 C20 109.61(13) . . ?
C20 C11 H11 109.1 . . ?
N9 N12 C5 109.08(14) . . ?
C7 C13 H13 119.6 . . ?
C22 C13 C7 120.7(2) . . ?
C22 C13 H13 119.6 . . ?
C19 C15 S1 118.95(17) . . ?
C24 C15 S1 120.33(17) . . ?
C24 C15 C19 120.7(2) . . ?
C10 C17 H17 119.8 . . ?
C25 C17 C10 120.4(2) . . ?
C25 C17 H17 119.8 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C18 H18A 109.5 . . ?
C20 C18 H18B 109.5 . . ?
C20 C18 H18C 109.5 . . ?
C15 C19 H19 120.6 . . ?
C15 C19 C27 118.7(2) . . ?
C27 C19 H19 120.6 . . ?
S1 C20 H20 105.5 . . ?
C11 C20 S1 112.72(12) . . ?
C11 C20 H20 105.5 . . ?
C18 C20 S1 111.76(15) . . ?
C18 C20 C11 114.96(16) . . ?
C18 C20 H20 105.5 . . ?
C5 C21 H21 121.3 . . ?
C26 C21 C5 117.48(19) . . ?
C26 C21 H21 121.3 . . ?
C13 C22 H22 119.8 . . ?
C25 C22 C13 120.3(2) . . ?
C25 C22 H22 119.8 . . ?
C4 C23 H23 118.7 . . ?
C4 C23 C26 122.6(2) . . ?
C26 C23 H23 118.7 . . ?
C15 C24 H24 120.5 . . ?
C15 C24 C29 119.0(2) . . ?
C29 C24 H24 120.5 . . ?
C17 C25 C22 119.6(2) . . ?
C17 C25 H25 120.2 . . ?
C22 C25 H25 120.2 . . ?
C21 C26 C23 121.1(2) . . ?
C21 C26 H26 119.5 . . ?
C23 C26 H26 119.5 . . ?
C19 C27 H27 119.8 . . ?
C30 C27 C19 120.5(2) . . ?
C30 C27 H27 119.8 . . ?
C6 C28 H28A 109.5 . . ?
C6 C28 H28B 109.5 . . ?
C6 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C24 C29 H29 119.9 . . ?
C30 C29 C24 120.1(3) . . ?
C30 C29 H29 119.9 . . ?
C27 C30 C29 120.8(3) . . ?
C27 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C15 C19 C27 -178.10(16) . . . . ?
S1 C15 C24 C29 178.12(19) . . . . ?
N2 C11 C20 S1 75.53(17) . . . . ?
N2 C11 C20 C18 -54.1(2) . . . . ?
N3 N9 N12 C5 -0.3(2) . . . . ?
C4 C23 C26 C21 -0.9(4) . . . . ?
C5 C21 C26 C23 0.8(3) . . . . ?
C6 N2 C11 C7 99.81(19) . . . . ?
C6 N2 C11 C20 -139.47(17) . . . . ?
C6 N3 C8 C4 5.6(3) . . . . ?
C6 N3 C8 C5 -174.93(17) . . . . ?
C6 N3 N9 N12 175.85(16) . . . . ?
C7 C10 C17 C25 -0.4(3) . . . . ?
C7 C11 C20 S1 -162.80(13) . . . . ?
C7 C11 C20 C18 67.6(2) . . . . ?
C7 C13 C22 C25 -0.2(3) . . . . ?
C8 N3 C6 N2 -0.1(3) . . . . ?
C8 N3 C6 C28 178.14(19) . . . . ?
C8 N3 N9 N12 -0.2(2) . . . . ?
C8 C4 C23 C26 0.2(3) . . . . ?
C8 C5 N12 N9 0.6(2) . . . . ?
C8 C5 C21 C26 0.0(3) . . . . ?
N9 N3 C6 N2 -175.11(16) . . . . ?
N9 N3 C6 C28 3.1(3) . . . . ?
N9 N3 C8 C4 -179.0(2) . . . . ?
N9 N3 C8 C5 0.52(18) . . . . ?
C10 C7 C11 N2 12.5(2) . . . . ?
C10 C7 C11 C20 -107.7(2) . . . . ?
C10 C7 C13 C22 0.6(3) . . . . ?
C10 C17 C25 C22 0.7(3) . . . . ?
C11 N2 C6 N3 178.14(14) . . . . ?
C11 N2 C6 C28 0.3(3) . . . . ?
C11 C7 C10 C17 179.45(18) . . . . ?
C11 C7 C13 C22 -179.15(18) . . . . ?
N12 C5 C8 N3 -0.70(19) . . . . ?
N12 C5 C8 C4 178.88(17) . . . . ?
N12 C5 C21 C26 -179.5(2) . . . . ?
C13 C7 C10 C17 -0.3(3) . . . . ?
C13 C7 C11 N2 -167.80(16) . . . . ?
C13 C7 C11 C20 72.0(2) . . . . ?
C13 C22 C25 C17 -0.4(3) . . . . ?
O14 S1 C15 C19 -144.54(17) . . . . ?
O14 S1 C15 C24 35.4(2) . . . . ?
O14 S1 C20 C11 175.84(15) . . . . ?
O14 S1 C20 C18 -52.89(17) . . . . ?
C15 S1 C20 C11 -68.92(16) . . . . ?
C15 S1 C20 C18 62.35(15) . . . . ?
C15 C19 C27 C30 0.0(3) . . . . ?
C15 C24 C29 C30 0.0(4) . . . . ?
O16 S1 C15 C19 -15.19(19) . . . . ?
O16 S1 C15 C24 164.75(18) . . . . ?
O16 S1 C20 C11 47.77(17) . . . . ?
O16 S1 C20 C18 179.04(14) . . . . ?
C19 C15 C24 C29 -1.9(3) . . . . ?
C19 C27 C30 C29 -1.9(4) . . . . ?
C20 S1 C15 C19 101.08(17) . . . . ?
C20 S1 C15 C24 -78.98(19) . . . . ?
C21 C5 C8 N3 179.74(17) . . . . ?
C21 C5 C8 C4 -0.7(3) . . . . ?
C21 C5 N12 N9 -179.9(2) . . . . ?
C23 C4 C8 N3 180.00(19) . . . . ?
C23 C4 C8 C5 0.6(3) . . . . ?
C24 C15 C19 C27 2.0(3) . . . . ?
C24 C29 C30 C27 2.0(4) . . . . ?

_olex2_date_sample_data_collection 2020-06-03
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.723
_oxdiff_exptl_absorpt_empirical_full_min 0.558
