# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_202304101_auto
_database_code_depnum_ccdc_archive 'CCDC 2287151'
loop_
_audit_author_name
_audit_author_address
'Mei guangjian'
;JiangSu normal universtiy
China
;
_audit_update_record             
;
2023-08-07 deposited with the CCDC.	2024-05-31 downloaded from the CCDC.
;
_audit_creation_date             2023-04-27
_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         'C35 H26 Cl N3 O2 S'
_chemical_formula_sum            'C35 H26 Cl N3 O2 S'
_chemical_formula_weight         588.10
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N1S1Cl1
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.41446(16)
_cell_length_b                   17.8154(4)
_cell_length_c                   29.7331(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3397.78(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4576
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.0690
_cell_measurement_theta_min      3.8670
_shelx_estimated_absorpt_T_max   0.839
_shelx_estimated_absorpt_T_min   0.759
_exptl_absorpt_coefficient_mu    1.825
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
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    1.150
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12228
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.446
_diffrn_reflns_theta_min         5.107
_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 0.997
_diffrn_measured_fraction_theta_max 0.987
_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  37.00   1.00    3.00    --  -33.50  37.00  90.00   93
  2  ω   -105.00  38.00   1.00    3.00    --  -33.50   0.00  90.00  143
  3  ω   -101.00 -44.00   1.00    3.00    --  -33.50 -57.00 150.00   57
  4  ω     66.00  94.00   1.00    3.00    --   36.47 178.00  60.00   28
  5  ω    105.00 167.00   1.00   15.00    --  108.00  77.00 -90.00   62
  6  ω     40.00 104.00   1.00   15.00    --  108.00-111.00   0.00   64
  7  ω     41.00 117.00   1.00   15.00    --  108.00 -61.00-150.00   76
  8  ω    111.00 164.00   1.00   15.00    --  108.00 111.00 -60.00   53
  9  ω     88.00 157.00   1.00   15.00    --  108.00  61.00  30.00   69
 10  ω     46.00 107.00   1.00   15.00    --  108.00 -94.00 150.00   61
 11  ω     51.00 135.00   1.00   15.00    --  108.00 -15.00-180.00   84
;
_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      0.0874098000
_diffrn_orient_matrix_UB_12      0.0638150000
_diffrn_orient_matrix_UB_13      -0.0294193000
_diffrn_orient_matrix_UB_21      -0.1655589000
_diffrn_orient_matrix_UB_22      -0.0170419000
_diffrn_orient_matrix_UB_23      -0.0361465000
_diffrn_orient_matrix_UB_31      -0.1503685000
_diffrn_orient_matrix_UB_32      0.0557842000
_diffrn_orient_matrix_UB_33      0.0226804000
_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         0.728
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                5347
_reflns_number_total             6339
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_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         0.151
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1931 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6339
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.003
_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)+(0.0596P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1176
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C29(H29A,H29B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C12(H12), C14(H14), C15(H15), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28),
  C31(H31), C32(H32), C33(H33), C34(H34), C35(H35)
;
_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 0.3402(3) -0.19104(7) 0.50767(5) 0.0997(5) Uani 1 1 d . . . . .
S1 S 0.10586(14) 0.05264(5) 0.60896(3) 0.0501(2) Uani 1 1 d . . . . .
O1 O -0.0469(4) 0.15752(17) 0.65668(10) 0.0653(7) Uani 1 1 d . . . . .
O2 O 0.0910(4) 0.25831(15) 0.68630(9) 0.0598(6) Uani 1 1 d . . . . .
N1 N 0.4811(5) 0.10250(15) 0.59242(9) 0.0470(6) Uani 1 1 d . . . . .
N2 N 0.2892(4) 0.18410(15) 0.63855(8) 0.0424(6) Uani 1 1 d . . . . .
N3 N 0.3792(6) 0.44282(17) 0.78413(10) 0.0576(7) Uani 1 1 d . . . . .
C1 C 0.2275(7) -0.0723(2) 0.55693(13) 0.0619(9) Uani 1 1 d . . . . .
H1 H 0.1001 -0.0961 0.5613 0.074 Uiso 1 1 calc R . . . .
C2 C 0.3828(8) -0.1031(2) 0.53191(14) 0.0689(11) Uani 1 1 d . . . . .
C3 C 0.5761(7) -0.0693(2) 0.52522(13) 0.0645(10) Uani 1 1 d . . . . .
H3 H 0.6769 -0.0927 0.5077 0.077 Uiso 1 1 calc R . . . .
C4 C 0.6168(7) -0.0002(2) 0.54507(12) 0.0589(9) Uani 1 1 d . . . . .
H4 H 0.7454 0.0231 0.5412 0.071 Uiso 1 1 calc R . . . .
C5 C 0.4622(6) 0.03360(18) 0.57077(11) 0.0470(7) Uani 1 1 d . . . . .
C6 C 0.2728(6) -0.00205(19) 0.57573(11) 0.0503(8) Uani 1 1 d . . . . .
C7 C 0.3106(5) 0.11839(16) 0.61324(11) 0.0416(6) Uani 1 1 d . . . . .
C8 C 0.1061(5) 0.1969(2) 0.66002(11) 0.0495(7) Uani 1 1 d . . . . .
C9 C 0.4689(5) 0.23715(18) 0.63678(11) 0.0433(7) Uani 1 1 d . . . . .
H9 H 0.5973 0.2082 0.6410 0.052 Uiso 1 1 calc R . . . .
C10 C 0.4500(5) 0.29219(18) 0.67503(10) 0.0436(7) Uani 1 1 d . . . . .
C11 C 0.2666(5) 0.30070(19) 0.69758(12) 0.0475(7) Uani 1 1 d . . . . .
C12 C 0.2366(6) 0.34966(19) 0.73316(12) 0.0495(7) Uani 1 1 d . . . . .
H12 H 0.1081 0.3521 0.7476 0.059 Uiso 1 1 calc R . . . .
C13 C 0.4010(6) 0.39543(18) 0.74726(11) 0.0494(7) Uani 1 1 d . . . . .
C14 C 0.5880(6) 0.3894(2) 0.72321(12) 0.0537(8) Uani 1 1 d . . . . .
H14 H 0.6994 0.4202 0.7309 0.064 Uiso 1 1 calc R . . . .
C15 C 0.6111(6) 0.33891(19) 0.68841(11) 0.0515(7) Uani 1 1 d . . . . .
H15 H 0.7384 0.3362 0.6735 0.062 Uiso 1 1 calc R . . . .
C16 C 0.4812(6) 0.27634(19) 0.59139(12) 0.0492(7) Uani 1 1 d . . . . .
C17 C 0.6606(8) 0.2730(3) 0.56633(16) 0.0739(12) Uani 1 1 d . . . . .
H17 H 0.7731 0.2450 0.5767 0.089 Uiso 1 1 calc R . . . .
C18 C 0.6764(11) 0.3108(3) 0.52563(18) 0.0996(19) Uani 1 1 d . . . . .
H18 H 0.7994 0.3085 0.5091 0.120 Uiso 1 1 calc R . . . .
C19 C 0.5116(13) 0.3514(4) 0.5098(2) 0.114(2) Uani 1 1 d . . . . .
H19 H 0.5214 0.3761 0.4823 0.137 Uiso 1 1 calc R . . . .
C20 C 0.3292(11) 0.3559(3) 0.5349(2) 0.105(2) Uani 1 1 d . . . . .
H20 H 0.2166 0.3841 0.5247 0.126 Uiso 1 1 calc R . . . .
C21 C 0.3186(8) 0.3174(3) 0.57540(16) 0.0782(13) Uani 1 1 d . . . . .
H21 H 0.1963 0.3198 0.5922 0.094 Uiso 1 1 calc R . . . .
C22 C 0.5380(7) 0.4988(2) 0.79495(13) 0.0589(9) Uani 1 1 d . . . . .
H22A H 0.6733 0.4745 0.7939 0.071 Uiso 1 1 calc R . . . .
H22B H 0.5156 0.5155 0.8256 0.071 Uiso 1 1 calc R . . . .
C23 C 0.5451(6) 0.5666(2) 0.76521(13) 0.0575(9) Uani 1 1 d . . . . .
C24 C 0.7260(8) 0.5875(3) 0.7442(2) 0.0856(14) Uani 1 1 d . . . . .
H24 H 0.8463 0.5592 0.7482 0.103 Uiso 1 1 calc R . . . .
C25 C 0.7311(12) 0.6505(4) 0.7171(2) 0.108(2) Uani 1 1 d . . . . .
H25 H 0.8535 0.6630 0.7021 0.130 Uiso 1 1 calc R . . . .
C26 C 0.5588(12) 0.6944(3) 0.7121(2) 0.1001(19) Uani 1 1 d . . . . .
H26 H 0.5631 0.7373 0.6942 0.120 Uiso 1 1 calc R . . . .
C27 C 0.3829(12) 0.6747(3) 0.7334(2) 0.1030(18) Uani 1 1 d . . . . .
H27 H 0.2641 0.7041 0.7301 0.124 Uiso 1 1 calc R . . . .
C28 C 0.3747(9) 0.6114(2) 0.76037(19) 0.0813(13) Uani 1 1 d . . . . .
H28 H 0.2517 0.5993 0.7753 0.098 Uiso 1 1 calc R . . . .
C29 C 0.1814(6) 0.44546(19) 0.80753(12) 0.0586(9) Uani 1 1 d . . . . .
H29A H 0.0708 0.4499 0.7854 0.070 Uiso 1 1 calc R . . . .
H29B H 0.1781 0.4903 0.8260 0.070 Uiso 1 1 calc R . . . .
C30 C 0.1365(7) 0.37798(19) 0.83715(11) 0.0548(9) Uani 1 1 d . . . . .
C31 C 0.2831(8) 0.3522(3) 0.86707(14) 0.0718(11) Uani 1 1 d . . . . .
H31 H 0.4117 0.3761 0.8687 0.086 Uiso 1 1 calc R . . . .
C32 C 0.2437(10) 0.2917(3) 0.89469(16) 0.0854(14) Uani 1 1 d . . . . .
H32 H 0.3445 0.2752 0.9149 0.102 Uiso 1 1 calc R . . . .
C33 C 0.0540(10) 0.2560(2) 0.89211(16) 0.0829(14) Uani 1 1 d . . . . .
H33 H 0.0268 0.2148 0.9104 0.099 Uiso 1 1 calc R . . . .
C34 C -0.0936(9) 0.2805(3) 0.86295(16) 0.0784(12) Uani 1 1 d . . . . .
H34 H -0.2221 0.2564 0.8614 0.094 Uiso 1 1 calc R . . . .
C35 C -0.0524(8) 0.3414(2) 0.83558(14) 0.0677(11) Uani 1 1 d . . . . .
H35 H -0.1544 0.3581 0.8157 0.081 Uiso 1 1 calc R . . . .


_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 C2 1.746(4) . ?
S1 C6 1.753(4) . ?
S1 C7 1.764(3) . ?
O1 C8 1.210(4) . ?
O2 C8 1.348(4) . ?
O2 C11 1.397(4) . ?
N1 C5 1.391(4) . ?
N1 C7 1.288(4) . ?
N2 C7 1.399(4) . ?
N2 C8 1.356(4) . ?
N2 C9 1.491(4) . ?
N3 C13 1.391(4) . ?
N3 C22 1.461(5) . ?
N3 C29 1.448(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.359(6) . ?
C1 C6 1.401(5) . ?
C2 C3 1.392(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(5) . ?
C5 C6 1.379(5) . ?
C9 H9 0.9800 . ?
C9 C10 1.506(4) . ?
C9 C16 1.522(5) . ?
C10 C11 1.363(5) . ?
C10 C15 1.386(5) . ?
C11 C12 1.384(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.398(5) . ?
C13 C14 1.400(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(6) . ?
C16 C21 1.361(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.364(9) . ?
C19 H19 0.9300 . ?
C19 C20 1.390(9) . ?
C20 H20 0.9300 . ?
C20 C21 1.387(7) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.498(5) . ?
C23 C24 1.370(7) . ?
C23 C28 1.361(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.381(7) . ?
C25 H25 0.9300 . ?
C25 C26 1.363(9) . ?
C26 H26 0.9300 . ?
C26 C27 1.342(9) . ?
C27 H27 0.9300 . ?
C27 C28 1.384(7) . ?
C28 H28 0.9300 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.518(5) . ?
C30 C31 1.373(6) . ?
C30 C35 1.376(6) . ?
C31 H31 0.9300 . ?
C31 C32 1.378(6) . ?
C32 H32 0.9300 . ?
C32 C33 1.376(8) . ?
C33 H33 0.9300 . ?
C33 C34 1.356(7) . ?
C34 H34 0.9300 . ?
C34 C35 1.382(6) . ?
C35 H35 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
C6 S1 C7 87.42(16) . . ?
C8 O2 C11 121.4(3) . . ?
C7 N1 C5 110.0(3) . . ?
C7 N2 C9 115.8(2) . . ?
C8 N2 C7 118.6(3) . . ?
C8 N2 C9 125.4(3) . . ?
C13 N3 C22 121.2(3) . . ?
C13 N3 C29 119.1(3) . . ?
C29 N3 C22 118.9(3) . . ?
C2 C1 H1 122.4 . . ?
C2 C1 C6 115.3(4) . . ?
C6 C1 H1 122.4 . . ?
C1 C2 Cl1 118.3(4) . . ?
C1 C2 C3 123.8(4) . . ?
C3 C2 Cl1 117.9(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.3(4) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.9(4) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 N1 125.1(3) . . ?
C6 C5 N1 115.7(3) . . ?
C6 C5 C4 119.2(3) . . ?
C1 C6 S1 126.5(3) . . ?
C5 C6 S1 110.0(3) . . ?
C5 C6 C1 123.5(4) . . ?
N1 C7 S1 116.8(2) . . ?
N1 C7 N2 121.7(3) . . ?
N2 C7 S1 121.4(2) . . ?
O1 C8 O2 117.4(3) . . ?
O1 C8 N2 124.5(3) . . ?
O2 C8 N2 118.1(3) . . ?
N2 C9 H9 108.2 . . ?
N2 C9 C10 108.9(3) . . ?
N2 C9 C16 111.2(3) . . ?
C10 C9 H9 108.2 . . ?
C10 C9 C16 112.0(3) . . ?
C16 C9 H9 108.2 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 C15 115.8(3) . . ?
C15 C10 C9 123.2(3) . . ?
C10 C11 O2 121.2(3) . . ?
C10 C11 C12 124.5(3) . . ?
C12 C11 O2 114.3(3) . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.5(3) . . ?
C13 C12 H12 120.3 . . ?
N3 C13 C12 121.0(3) . . ?
N3 C13 C14 122.4(3) . . ?
C12 C13 C14 116.6(3) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 C13 121.7(4) . . ?
C15 C14 H14 119.1 . . ?
C10 C15 H15 119.1 . . ?
C14 C15 C10 121.8(3) . . ?
C14 C15 H15 119.1 . . ?
C17 C16 C9 120.4(4) . . ?
C21 C16 C9 121.1(3) . . ?
C21 C16 C17 118.5(4) . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.9(5) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.1(5) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.9(5) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 120.7 . . ?
C21 C20 C19 118.6(6) . . ?
C21 C20 H20 120.7 . . ?
C16 C21 C20 122.1(5) . . ?
C16 C21 H21 118.9 . . ?
C20 C21 H21 118.9 . . ?
N3 C22 H22A 108.2 . . ?
N3 C22 H22B 108.2 . . ?
N3 C22 C23 116.2(3) . . ?
H22A C22 H22B 107.4 . . ?
C23 C22 H22A 108.2 . . ?
C23 C22 H22B 108.2 . . ?
C24 C23 C22 121.0(4) . . ?
C28 C23 C22 120.7(4) . . ?
C28 C23 C24 118.2(4) . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.5(5) . . ?
C25 C24 H24 119.7 . . ?
C24 C25 H25 119.6 . . ?
C26 C25 C24 120.7(6) . . ?
C26 C25 H25 119.6 . . ?
C25 C26 H26 120.7 . . ?
C27 C26 C25 118.7(5) . . ?
C27 C26 H26 120.7 . . ?
C26 C27 H27 119.3 . . ?
C26 C27 C28 121.3(6) . . ?
C28 C27 H27 119.3 . . ?
C23 C28 C27 120.5(6) . . ?
C23 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
N3 C29 H29A 108.6 . . ?
N3 C29 H29B 108.6 . . ?
N3 C29 C30 114.8(3) . . ?
H29A C29 H29B 107.5 . . ?
C30 C29 H29A 108.6 . . ?
C30 C29 H29B 108.6 . . ?
C31 C30 C29 120.7(4) . . ?
C31 C30 C35 117.8(4) . . ?
C35 C30 C29 121.5(4) . . ?
C30 C31 H31 119.3 . . ?
C30 C31 C32 121.4(5) . . ?
C32 C31 H31 119.3 . . ?
C31 C32 H32 120.3 . . ?
C33 C32 C31 119.4(5) . . ?
C33 C32 H32 120.3 . . ?
C32 C33 H33 119.9 . . ?
C34 C33 C32 120.2(4) . . ?
C34 C33 H33 119.9 . . ?
C33 C34 H34 120.1 . . ?
C33 C34 C35 119.7(5) . . ?
C35 C34 H34 120.1 . . ?
C30 C35 C34 121.3(4) . . ?
C30 C35 H35 119.3 . . ?
C34 C35 H35 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C2 C3 C4 -178.3(3) . . . . ?
O2 C11 C12 C13 -179.5(3) . . . . ?
N1 C5 C6 S1 0.3(4) . . . . ?
N1 C5 C6 C1 -178.9(3) . . . . ?
N2 C9 C10 C11 -16.1(4) . . . . ?
N2 C9 C10 C15 166.5(3) . . . . ?
N2 C9 C16 C17 -124.6(4) . . . . ?
N2 C9 C16 C21 57.7(5) . . . . ?
N3 C13 C14 C15 176.1(3) . . . . ?
N3 C22 C23 C24 -125.7(4) . . . . ?
N3 C22 C23 C28 58.0(5) . . . . ?
N3 C29 C30 C31 48.9(5) . . . . ?
N3 C29 C30 C35 -132.3(4) . . . . ?
C1 C2 C3 C4 0.3(7) . . . . ?
C2 C1 C6 S1 179.2(3) . . . . ?
C2 C1 C6 C5 -1.7(6) . . . . ?
C2 C3 C4 C5 -0.6(6) . . . . ?
C3 C4 C5 N1 -179.9(3) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 S1 -179.3(3) . . . . ?
C4 C5 C6 C1 1.5(5) . . . . ?
C5 N1 C7 S1 -0.5(4) . . . . ?
C5 N1 C7 N2 178.7(3) . . . . ?
C6 S1 C7 N1 0.5(3) . . . . ?
C6 S1 C7 N2 -178.7(3) . . . . ?
C6 C1 C2 Cl1 179.4(3) . . . . ?
C6 C1 C2 C3 0.8(6) . . . . ?
C7 S1 C6 C1 178.7(3) . . . . ?
C7 S1 C6 C5 -0.4(3) . . . . ?
C7 N1 C5 C4 179.7(3) . . . . ?
C7 N1 C5 C6 0.1(4) . . . . ?
C7 N2 C8 O1 -4.8(5) . . . . ?
C7 N2 C8 O2 176.4(3) . . . . ?
C7 N2 C9 C10 -163.8(3) . . . . ?
C7 N2 C9 C16 72.2(3) . . . . ?
C8 O2 C11 C10 14.7(5) . . . . ?
C8 O2 C11 C12 -164.5(3) . . . . ?
C8 N2 C7 S1 -0.1(4) . . . . ?
C8 N2 C7 N1 -179.3(3) . . . . ?
C8 N2 C9 C10 20.6(4) . . . . ?
C8 N2 C9 C16 -103.4(4) . . . . ?
C9 N2 C7 S1 -176.0(2) . . . . ?
C9 N2 C7 N1 4.8(4) . . . . ?
C9 N2 C8 O1 170.6(3) . . . . ?
C9 N2 C8 O2 -8.1(5) . . . . ?
C9 C10 C11 O2 0.6(5) . . . . ?
C9 C10 C11 C12 179.7(3) . . . . ?
C9 C10 C15 C14 179.2(3) . . . . ?
C9 C16 C17 C18 -177.6(5) . . . . ?
C9 C16 C21 C20 177.6(5) . . . . ?
C10 C9 C16 C17 113.3(4) . . . . ?
C10 C9 C16 C21 -64.5(5) . . . . ?
C10 C11 C12 C13 1.3(5) . . . . ?
C11 O2 C8 O1 170.3(3) . . . . ?
C11 O2 C8 N2 -10.9(5) . . . . ?
C11 C10 C15 C14 1.7(5) . . . . ?
C11 C12 C13 N3 -177.1(3) . . . . ?
C11 C12 C13 C14 1.2(5) . . . . ?
C12 C13 C14 C15 -2.2(5) . . . . ?
C13 N3 C22 C23 74.3(5) . . . . ?
C13 N3 C29 C30 74.8(4) . . . . ?
C13 C14 C15 C10 0.8(6) . . . . ?
C15 C10 C11 O2 178.2(3) . . . . ?
C15 C10 C11 C12 -2.7(5) . . . . ?
C16 C9 C10 C11 107.4(4) . . . . ?
C16 C9 C10 C15 -70.0(4) . . . . ?
C16 C17 C18 C19 -0.6(9) . . . . ?
C17 C16 C21 C20 -0.2(8) . . . . ?
C17 C18 C19 C20 1.1(11) . . . . ?
C18 C19 C20 C21 -1.1(11) . . . . ?
C19 C20 C21 C16 0.6(10) . . . . ?
C21 C16 C17 C18 0.2(7) . . . . ?
C22 N3 C13 C12 -170.6(3) . . . . ?
C22 N3 C13 C14 11.1(5) . . . . ?
C22 N3 C29 C30 -115.5(4) . . . . ?
C22 C23 C24 C25 -179.6(5) . . . . ?
C22 C23 C28 C27 178.9(4) . . . . ?
C23 C24 C25 C26 2.5(9) . . . . ?
C24 C23 C28 C27 2.5(8) . . . . ?
C24 C25 C26 C27 -1.1(10) . . . . ?
C25 C26 C27 C28 0.5(10) . . . . ?
C26 C27 C28 C23 -1.2(9) . . . . ?
C28 C23 C24 C25 -3.1(8) . . . . ?
C29 N3 C13 C12 -1.2(5) . . . . ?
C29 N3 C13 C14 -179.4(3) . . . . ?
C29 N3 C22 C23 -95.2(4) . . . . ?
C29 C30 C31 C32 179.0(4) . . . . ?
C29 C30 C35 C34 -179.3(4) . . . . ?
C30 C31 C32 C33 0.4(7) . . . . ?
C31 C30 C35 C34 -0.4(6) . . . . ?
C31 C32 C33 C34 -0.7(8) . . . . ?
C32 C33 C34 C35 0.4(8) . . . . ?
C33 C34 C35 C30 0.1(7) . . . . ?
C35 C30 C31 C32 0.1(6) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.899 -0.034 0.393 191.4 50.6 ?
2 -0.433 0.034 0.893 191.4 51.1 ?
3 -0.803 0.466 0.107 191.4 50.0 ?
4 -0.932 0.534 0.607 191.4 50.1 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.446
_oxdiff_exptl_absorpt_empirical_full_min 0.845
####################################################################### 
# 
# 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_230508_wqangz_047965_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2287152'
loop_
_audit_author_name
_audit_author_address
'Mei guangjian'
;JiangSu normal universtiy
China
;
_audit_update_record             
;
2023-08-07 deposited with the CCDC.	2024-05-31 downloaded from the CCDC.
;
_audit_creation_date             2023-05-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C35 H26 Cl N3 O2 S'
_chemical_formula_sum            'C35 H26 Cl N3 O2 S'
_chemical_formula_weight         588.10
_chemical_absolute_configuration AD
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.3743(3)
_cell_length_b                   17.8083(8)
_cell_length_c                   29.5159(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3350.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6527
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.75
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1153 before and 0.0605 after correction.
The Ratio of minimum to maximum transmission is 0.9153.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            28414
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.380
_diffrn_reflns_theta_min         1.792
_diffrn_ambient_temperature      193.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                5152
_reflns_number_total             6840
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1739 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6840
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      0.976
_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)+(0.0584P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1115
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C29(H29A,H29B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26),
  C31(H31), C32(H32), C33(H33), C34(H34), C35(H35)
;
_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
Cl1 Cl 0.3580(2) 1.19438(6) 0.50799(4) 0.0606(3) Uani 1 1 d . . . . .
S1 S 0.11607(14) 0.95012(5) 0.60892(3) 0.0327(2) Uani 1 1 d . . . . .
O1 O -0.0423(4) 0.84483(15) 0.65551(9) 0.0426(7) Uani 1 1 d . . . . .
O2 O 0.0904(4) 0.74261(13) 0.68490(8) 0.0382(6) Uani 1 1 d . . . . .
N1 N 0.4929(5) 0.89892(15) 0.59189(10) 0.0292(7) Uani 1 1 d . . . . .
N2 N 0.2957(4) 0.81718(15) 0.63779(9) 0.0282(6) Uani 1 1 d . . . . .
N3 N 0.3701(5) 0.55586(16) 0.78312(10) 0.0363(7) Uani 1 1 d . . . . .
C1 C 0.4004(7) 1.1066(2) 0.53209(13) 0.0433(10) Uani 1 1 d . . . . .
C2 C 0.5915(7) 1.0716(2) 0.52523(13) 0.0410(9) Uani 1 1 d . . . . .
H2 H 0.695563 1.095137 0.507107 0.049 Uiso 1 1 calc R . . . .
C3 C 0.6319(6) 1.00196(19) 0.54477(11) 0.0364(9) Uani 1 1 d . . . . .
H3 H 0.763786 0.978071 0.540630 0.044 Uiso 1 1 calc R . . . .
C4 C 0.4751(6) 0.96792(18) 0.57055(11) 0.0282(8) Uani 1 1 d . . . . .
C5 C 0.2834(6) 1.00400(19) 0.57643(11) 0.0314(8) Uani 1 1 d . . . . .
C6 C 0.2416(7) 1.0746(2) 0.55727(12) 0.0380(9) Uani 1 1 d . . . . .
H6 H 0.110599 1.099062 0.561446 0.046 Uiso 1 1 calc R . . . .
C7 C 0.3183(5) 0.88338(18) 0.61267(11) 0.0294(8) Uani 1 1 d . . . . .
C8 C 0.4761(5) 0.76313(18) 0.63610(11) 0.0276(7) Uani 1 1 d . . . . .
H8 H 0.608904 0.791956 0.640831 0.033 Uiso 1 1 calc R . . . .
C9 C 0.4877(6) 0.72475(19) 0.59035(12) 0.0320(8) Uani 1 1 d . . . . .
C10 C 0.6693(6) 0.7281(2) 0.56547(13) 0.0457(10) Uani 1 1 d . . . . .
H10 H 0.784569 0.756740 0.576303 0.055 Uiso 1 1 calc R . . . .
C11 C 0.6862(8) 0.6896(2) 0.52423(15) 0.0593(13) Uani 1 1 d . . . . .
H11 H 0.813063 0.691709 0.507398 0.071 Uiso 1 1 calc R . . . .
C12 C 0.5195(8) 0.6488(3) 0.50815(16) 0.0635(13) Uani 1 1 d . . . . .
H12 H 0.531330 0.622486 0.480266 0.076 Uiso 1 1 calc R . . . .
C13 C 0.3337(8) 0.6459(2) 0.53253(15) 0.0589(12) Uani 1 1 d . . . . .
H13 H 0.216840 0.618645 0.521236 0.071 Uiso 1 1 calc R . . . .
C14 C 0.3208(6) 0.6834(2) 0.57359(14) 0.0456(10) Uani 1 1 d . . . . .
H14 H 0.194562 0.680669 0.590632 0.055 Uiso 1 1 calc R . . . .
C15 C 0.4527(5) 0.70762(19) 0.67442(11) 0.0281(8) Uani 1 1 d . . . . .
C16 C 0.6135(6) 0.66024(19) 0.68773(12) 0.0344(8) Uani 1 1 d . . . . .
H16 H 0.745033 0.662984 0.672687 0.041 Uiso 1 1 calc R . . . .
C17 C 0.5868(6) 0.60902(19) 0.72245(12) 0.0342(9) Uani 1 1 d . . . . .
H17 H 0.699690 0.576842 0.730473 0.041 Uiso 1 1 calc R . . . .
C18 C 0.3963(6) 0.60354(18) 0.74611(11) 0.0317(8) Uani 1 1 d . . . . .
C19 C 0.2317(6) 0.65044(19) 0.73183(12) 0.0335(8) Uani 1 1 d . . . . .
H19 H 0.098821 0.648194 0.746350 0.040 Uiso 1 1 calc R . . . .
C20 C 0.2649(5) 0.69948(19) 0.69674(12) 0.0304(8) Uani 1 1 d . . . . .
C21 C 0.1084(6) 0.8049(2) 0.65915(12) 0.0327(8) Uani 1 1 d . . . . .
C22 C 0.3662(7) 0.3864(2) 0.76068(14) 0.0489(10) Uani 1 1 d . . . . .
H22 H 0.238469 0.399268 0.775304 0.059 Uiso 1 1 calc R . . . .
C23 C 0.3767(9) 0.3224(2) 0.73442(16) 0.0601(12) Uani 1 1 d . . . . .
H23 H 0.255615 0.291754 0.731294 0.072 Uiso 1 1 calc R . . . .
C24 C 0.5572(9) 0.3024(3) 0.71285(16) 0.0627(14) Uani 1 1 d . . . . .
H24 H 0.562450 0.258598 0.694515 0.075 Uiso 1 1 calc R . . . .
C25 C 0.7317(9) 0.3470(3) 0.71820(17) 0.0669(14) Uani 1 1 d . . . . .
H25 H 0.859363 0.333493 0.703718 0.080 Uiso 1 1 calc R . . . .
C26 C 0.7233(7) 0.4115(2) 0.74454(15) 0.0533(12) Uani 1 1 d . . . . .
H26 H 0.844817 0.441920 0.747863 0.064 Uiso 1 1 calc R . . . .
C27 C 0.5397(6) 0.4316(2) 0.76586(12) 0.0351(9) Uani 1 1 d . . . . .
C28 C 0.5295(6) 0.50064(19) 0.79560(12) 0.0367(9) Uani 1 1 d . . . . .
H28A H 0.503033 0.484373 0.827161 0.044 Uiso 1 1 calc R . . . .
H28B H 0.668341 0.525537 0.795012 0.044 Uiso 1 1 calc R . . . .
C29 C 0.1686(6) 0.55332(19) 0.80638(12) 0.0368(9) Uani 1 1 d . . . . .
H29A H 0.163811 0.507611 0.825448 0.044 Uiso 1 1 calc R . . . .
H29B H 0.055817 0.549076 0.783476 0.044 Uiso 1 1 calc R . . . .
C30 C 0.1250(7) 0.62101(19) 0.83597(12) 0.0352(8) Uani 1 1 d . . . . .
C31 C 0.2735(7) 0.6464(2) 0.86630(13) 0.0435(10) Uani 1 1 d . . . . .
H31 H 0.405676 0.621931 0.868224 0.052 Uiso 1 1 calc R . . . .
C32 C 0.2310(8) 0.7076(2) 0.89406(15) 0.0538(11) Uani 1 1 d . . . . .
H32 H 0.334677 0.724833 0.914704 0.065 Uiso 1 1 calc R . . . .
C33 C 0.0403(8) 0.7433(2) 0.89191(14) 0.0528(11) Uani 1 1 d . . . . .
H33 H 0.011813 0.784806 0.911198 0.063 Uiso 1 1 calc R . . . .
C34 C -0.1099(7) 0.7188(2) 0.86158(14) 0.0482(10) Uani 1 1 d . . . . .
H34 H -0.241496 0.743598 0.859558 0.058 Uiso 1 1 calc R . . . .
C35 C -0.0671(7) 0.6582(2) 0.83443(13) 0.0417(10) Uani 1 1 d . . . . .
H35 H -0.171675 0.641086 0.813952 0.050 Uiso 1 1 calc R . . . .


_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 C1 1.739(4) . ?
S1 C5 1.726(4) . ?
S1 C7 1.757(3) . ?
O1 C21 1.200(4) . ?
O2 C20 1.396(4) . ?
O2 C21 1.349(4) . ?
N1 C4 1.385(4) . ?
N1 C7 1.300(4) . ?
N2 C7 1.400(4) . ?
N2 C8 1.500(4) . ?
N2 C21 1.368(4) . ?
N3 C18 1.394(4) . ?
N3 C28 1.461(4) . ?
N3 C29 1.457(4) . ?
C1 C2 1.383(6) . ?
C1 C6 1.379(5) . ?
C2 C3 1.391(5) . ?
C3 C4 1.395(5) . ?
C4 C5 1.392(5) . ?
C5 C6 1.404(5) . ?
C8 C9 1.515(5) . ?
C8 C15 1.509(4) . ?
C9 C10 1.372(5) . ?
C9 C14 1.385(5) . ?
C10 C11 1.402(6) . ?
C11 C12 1.372(6) . ?
C12 C13 1.387(6) . ?
C13 C14 1.386(5) . ?
C15 C16 1.384(5) . ?
C15 C20 1.374(5) . ?
C16 C17 1.382(5) . ?
C17 C18 1.404(5) . ?
C18 C19 1.406(5) . ?
C19 C20 1.371(5) . ?
C22 C23 1.379(6) . ?
C22 C27 1.376(5) . ?
C23 C24 1.363(7) . ?
C24 C25 1.376(7) . ?
C25 C26 1.388(6) . ?
C26 C27 1.376(5) . ?
C27 C28 1.513(5) . ?
C29 C30 1.515(5) . ?
C30 C31 1.379(5) . ?
C30 C35 1.393(6) . ?
C31 C32 1.390(5) . ?
C32 C33 1.373(6) . ?
C33 C34 1.382(6) . ?
C34 C35 1.371(5) . ?

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
C5 S1 C7 87.57(17) . . ?
C21 O2 C20 121.7(3) . . ?
C7 N1 C4 109.5(3) . . ?
C7 N2 C8 116.3(3) . . ?
C21 N2 C7 118.0(3) . . ?
C21 N2 C8 125.5(3) . . ?
C18 N3 C28 121.6(3) . . ?
C18 N3 C29 119.6(3) . . ?
C29 N3 C28 118.2(3) . . ?
C2 C1 Cl1 118.8(3) . . ?
C2 C1 C6 122.6(3) . . ?
C6 C1 Cl1 118.5(3) . . ?
C1 C2 C3 120.3(4) . . ?
C2 C3 C4 118.7(4) . . ?
N1 C4 C3 125.1(3) . . ?
N1 C4 C5 115.1(3) . . ?
C5 C4 C3 119.8(3) . . ?
C4 C5 S1 110.8(2) . . ?
C4 C5 C6 122.0(3) . . ?
C6 C5 S1 127.2(3) . . ?
C1 C6 C5 116.6(4) . . ?
N1 C7 S1 117.0(3) . . ?
N1 C7 N2 121.2(3) . . ?
N2 C7 S1 121.8(3) . . ?
N2 C8 C9 110.9(3) . . ?
N2 C8 C15 108.6(3) . . ?
C15 C8 C9 112.2(3) . . ?
C10 C9 C8 119.9(3) . . ?
C10 C9 C14 118.7(3) . . ?
C14 C9 C8 121.4(3) . . ?
C9 C10 C11 120.6(4) . . ?
C12 C11 C10 120.0(4) . . ?
C11 C12 C13 120.1(4) . . ?
C12 C13 C14 119.1(4) . . ?
C9 C14 C13 121.5(4) . . ?
C16 C15 C8 122.6(3) . . ?
C20 C15 C8 120.9(3) . . ?
C20 C15 C16 116.4(3) . . ?
C17 C16 C15 121.4(3) . . ?
C16 C17 C18 121.4(3) . . ?
N3 C18 C17 122.4(3) . . ?
N3 C18 C19 120.5(3) . . ?
C17 C18 C19 117.1(3) . . ?
C20 C19 C18 119.3(3) . . ?
C15 C20 O2 121.1(3) . . ?
C19 C20 O2 114.6(3) . . ?
C19 C20 C15 124.3(3) . . ?
O1 C21 O2 118.0(3) . . ?
O1 C21 N2 124.2(3) . . ?
O2 C21 N2 117.8(3) . . ?
C23 C22 C27 120.4(4) . . ?
C24 C23 C22 121.3(5) . . ?
C23 C24 C25 118.6(4) . . ?
C24 C25 C26 120.7(4) . . ?
C27 C26 C25 120.2(4) . . ?
C22 C27 C28 120.4(3) . . ?
C26 C27 C22 118.7(4) . . ?
C26 C27 C28 120.9(4) . . ?
N3 C28 C27 115.5(3) . . ?
N3 C29 C30 114.1(3) . . ?
C31 C30 C29 120.6(4) . . ?
C31 C30 C35 118.0(3) . . ?
C35 C30 C29 121.4(3) . . ?
C30 C31 C32 120.4(4) . . ?
C33 C32 C31 120.6(4) . . ?
C32 C33 C34 119.8(4) . . ?
C35 C34 C33 119.3(4) . . ?
C34 C35 C30 122.0(4) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.975 0.034 0.393 187.9 44.5 ?
2 0.068 -0.034 0.893 187.9 44.5 ?
3 -0.632 0.466 0.607 187.9 44.3 ?
4 0.101 0.534 0.107 187.9 44.4 ?

_olex2_submission_special_instructions 'No special instructions were received'
