# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_i17648
_database_code_depnum_ccdc_archive 'CCDC 1940044'
loop_
_audit_author_name
_audit_author_address
'Chieh-Kai Chan' 'Academia Sinica'
_audit_update_record             
;
2019-07-12 deposited with the CCDC.	2019-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H20 Br N O2 S'
_chemical_formula_sum            'C28 H20 Br N O2 S'
_chemical_formula_weight         514.42

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   10.2950(15)
_cell_length_b                   15.616(2)
_cell_length_c                   14.892(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.857(4)
_cell_angle_gamma                90
_cell_volume                     2265.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9888
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      26.56

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.419
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.224
_exptl_absorpt_coefficient_mu    1.933
_shelx_estimated_absorpt_T_min   0.498
_shelx_estimated_absorpt_T_max   0.671
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7425
_exptl_absorpt_correction_T_max  0.8879
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            56268
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.946
_diffrn_reflns_theta_max         27.091
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4986
_reflns_number_gt                4227
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 740)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²+3.1678P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4986
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0914
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Br1 Br 1.18686(3) 0.78797(2) 0.69558(2) 0.02421(9) Uani 1 1 d . . . . .
S1 S 0.79154(6) 0.60139(3) 0.28800(4) 0.01331(12) Uani 1 1 d . . . . .
O1 O 0.90520(17) 0.54683(10) 0.33694(12) 0.0190(4) Uani 1 1 d . . . . .
O2 O 0.73317(19) 0.59425(11) 0.18669(12) 0.0213(4) Uani 1 1 d . . . . .
N1 N 0.4190(2) 0.54412(12) 0.30740(13) 0.0148(4) Uani 1 1 d . . . . .
C1 C 0.5304(2) 0.54326(14) 0.28175(16) 0.0141(4) Uani 1 1 d . . . . .
C2 C 0.6551(2) 0.58516(14) 0.33721(16) 0.0125(4) Uani 1 1 d . . . . .
C3 C 0.6654(2) 0.61891(14) 0.42541(16) 0.0124(4) Uani 1 1 d . . . . .
C4 C 0.5464(2) 0.61629(14) 0.45521(16) 0.0132(4) Uani 1 1 d . . . . .
C5 C 0.5447(2) 0.64770(15) 0.54407(16) 0.0171(5) Uani 1 1 d . . . . .
H5 H 0.626517 0.669753 0.588216 0.020 Uiso 1 1 calc R U . . .
C6 C 0.4265(3) 0.64654(17) 0.56678(17) 0.0212(5) Uani 1 1 d . . . . .
H6 H 0.426252 0.668354 0.626277 0.025 Uiso 1 1 calc R U . . .
C7 C 0.3044(3) 0.61306(17) 0.50223(18) 0.0207(5) Uani 1 1 d . . . . .
H7 H 0.222431 0.612847 0.518519 0.025 Uiso 1 1 calc R U . . .
C8 C 0.3031(2) 0.58090(16) 0.41641(17) 0.0182(5) Uani 1 1 d . . . . .
H8 H 0.220605 0.558271 0.373629 0.022 Uiso 1 1 calc R U . . .
C9 C 0.4235(2) 0.58131(14) 0.39153(16) 0.0146(5) Uani 1 1 d . . . . .
C10 C 0.5150(2) 0.49085(15) 0.19513(16) 0.0155(5) Uani 1 1 d . . . . .
C11 C 0.4017(2) 0.50356(16) 0.11446(17) 0.0186(5) Uani 1 1 d . . . . .
H11 H 0.337772 0.547733 0.113459 0.022 Uiso 1 1 calc R U . . .
C12 C 0.3820(3) 0.45172(17) 0.03555(17) 0.0220(5) Uani 1 1 d . . . . .
H12 H 0.305427 0.461162 -0.019776 0.026 Uiso 1 1 calc R U . . .
C13 C 0.4733(3) 0.38644(16) 0.03692(18) 0.0228(5) Uani 1 1 d . . . . .
H13 H 0.460296 0.351924 -0.017820 0.027 Uiso 1 1 calc R U . . .
C14 C 0.5834(3) 0.37130(16) 0.11788(19) 0.0224(5) Uani 1 1 d . . . . .
H14 H 0.643984 0.324980 0.119650 0.027 Uiso 1 1 calc R U . . .
C15 C 0.6053(2) 0.42397(16) 0.19677(17) 0.0186(5) Uani 1 1 d . . . . .
H15 H 0.682155 0.414311 0.251900 0.022 Uiso 1 1 calc R U . . .
C16 C 0.8434(2) 0.70902(14) 0.31190(15) 0.0124(4) Uani 1 1 d . . . . .
C17 C 0.7486(2) 0.77436(15) 0.27562(16) 0.0154(5) Uani 1 1 d . . . . .
H17 H 0.655465 0.761055 0.242009 0.018 Uiso 1 1 calc R U . . .
C18 C 0.7915(3) 0.85871(16) 0.28905(17) 0.0200(5) Uani 1 1 d . . . . .
H18 H 0.726998 0.903346 0.264671 0.024 Uiso 1 1 calc R U . . .
C19 C 0.9285(3) 0.87927(16) 0.33804(17) 0.0190(5) Uani 1 1 d . . . . .
C20 C 1.0213(3) 0.81266(16) 0.37275(18) 0.0197(5) Uani 1 1 d . . . . .
H20 H 1.114732 0.825679 0.405741 0.024 Uiso 1 1 calc R U . . .
C21 C 0.9798(2) 0.72754(15) 0.36000(17) 0.0166(5) Uani 1 1 d . . . . .
H21 H 1.044034 0.682719 0.383968 0.020 Uiso 1 1 calc R U . . .
C22 C 0.9742(3) 0.97157(17) 0.3530(2) 0.0327(7) Uani 1 1 d . . . . .
H22A H 1.035574 0.984021 0.316253 0.049 Uiso 1 1 calc R U . . .
H22B H 1.022984 0.981417 0.420548 0.049 Uiso 1 1 calc R U . . .
H22C H 0.893800 1.009154 0.332022 0.049 Uiso 1 1 calc R U . . .
C23 C 0.7929(2) 0.65847(14) 0.49145(15) 0.0127(4) Uani 1 1 d . . . . .
C24 C 0.7971(2) 0.74717(15) 0.50737(17) 0.0157(5) Uani 1 1 d . . . . .
H24 H 0.719463 0.781296 0.475493 0.019 Uiso 1 1 calc R U . . .
C25 C 0.9130(2) 0.78550(15) 0.56897(17) 0.0171(5) Uani 1 1 d . . . . .
H25 H 0.916241 0.845686 0.578752 0.020 Uiso 1 1 calc R U . . .
C26 C 1.0242(2) 0.73437(15) 0.61612(16) 0.0157(5) Uani 1 1 d . . . . .
C27 C 1.0207(2) 0.64620(15) 0.60477(17) 0.0159(5) Uani 1 1 d . . . . .
H27 H 1.096471 0.612051 0.639805 0.019 Uiso 1 1 calc R U . . .
C28 C 0.9050(2) 0.60840(15) 0.54154(16) 0.0146(5) Uani 1 1 d . . . . .
H28 H 0.902175 0.548130 0.532398 0.017 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
Br1 C26 1.904(2) . ?
S1 O2 1.4366(17) . ?
S1 O1 1.4405(17) . ?
S1 C16 1.765(2) . ?
S1 C2 1.800(2) . ?
N1 C1 1.322(3) . ?
N1 C9 1.368(3) . ?
C1 C2 1.440(3) . ?
C1 C10 1.492(3) . ?
C2 C3 1.387(3) . ?
C3 C4 1.432(3) . ?
C3 C23 1.496(3) . ?
C4 C5 1.417(3) . ?
C4 C9 1.422(3) . ?
C5 C6 1.365(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.413(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.369(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.404(3) . ?
C8 H8 0.9500 . ?
C10 C11 1.392(3) . ?
C10 C15 1.394(3) . ?
C11 C12 1.387(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.385(3) . ?
C16 C17 1.395(3) . ?
C17 C18 1.383(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.400(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.394(4) . ?
C19 C22 1.510(3) . ?
C20 C21 1.390(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C28 1.394(3) . ?
C23 C24 1.404(3) . ?
C24 C25 1.384(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.386(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.386(3) . ?
C27 C28 1.389(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 118.75(11) . . ?
O2 S1 C16 106.41(10) . . ?
O1 S1 C16 108.53(11) . . ?
O2 S1 C2 107.46(11) . . ?
O1 S1 C2 108.90(10) . . ?
C16 S1 C2 106.09(10) . . ?
C1 N1 C9 119.5(2) . . ?
N1 C1 C2 121.7(2) . . ?
N1 C1 C10 113.3(2) . . ?
C2 C1 C10 124.9(2) . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 S1 120.09(17) . . ?
C1 C2 S1 119.92(17) . . ?
C2 C3 C4 118.1(2) . . ?
C2 C3 C23 124.2(2) . . ?
C4 C3 C23 117.70(19) . . ?
C5 C4 C9 118.6(2) . . ?
C5 C4 C3 123.4(2) . . ?
C9 C4 C3 118.0(2) . . ?
C6 C5 C4 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.3(2) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.1(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
N1 C9 C8 117.9(2) . . ?
N1 C9 C4 122.3(2) . . ?
C8 C9 C4 119.8(2) . . ?
C11 C10 C15 119.4(2) . . ?
C11 C10 C1 119.6(2) . . ?
C15 C10 C1 120.8(2) . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C15 119.9(2) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
C21 C16 C17 120.9(2) . . ?
C21 C16 S1 119.57(18) . . ?
C17 C16 S1 119.36(18) . . ?
C18 C17 C16 119.3(2) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 121.0(2) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 118.5(2) . . ?
C20 C19 C22 120.9(2) . . ?
C18 C19 C22 120.6(2) . . ?
C21 C20 C19 121.3(2) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C16 C21 C20 119.1(2) . . ?
C16 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C28 C23 C24 119.2(2) . . ?
C28 C23 C3 121.3(2) . . ?
C24 C23 C3 119.4(2) . . ?
C25 C24 C23 120.8(2) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C26 118.7(2) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 H25 120.6 . . ?
C27 C26 C25 121.7(2) . . ?
C27 C26 Br1 119.72(18) . . ?
C25 C26 Br1 118.57(18) . . ?
C26 C27 C28 119.2(2) . . ?
C26 C27 H27 120.4 . . ?
C28 C27 H27 120.4 . . ?
C27 C28 C23 120.3(2) . . ?
C27 C28 H28 119.9 . . ?
C23 C28 H28 119.9 . . ?

_refine_diff_density_max         0.589
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_i17707
_database_code_depnum_ccdc_archive 'CCDC 1951575'
loop_
_audit_author_name
_audit_author_address
'Chieh-Kai Chan' 'Academia Sinica'
_audit_update_record             
;
2019-09-05 deposited with the CCDC.	2019-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 Cl N O3 S'
_chemical_formula_sum            'C23 H18 Cl N O3 S'
_chemical_formula_weight         423.89

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.4998(8)
_cell_length_b                   13.3726(11)
_cell_length_c                   15.4288(12)
_cell_angle_alpha                79.550(2)
_cell_angle_beta                 70.858(2)
_cell_angle_gamma                76.176(2)
_cell_volume                     1974.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9887
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      27.18

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.383
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.233
_exptl_absorpt_coefficient_mu    0.325
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.928
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9579
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45589
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.992
_diffrn_reflns_theta_max         27.105
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8723
_reflns_number_gt                7758
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 740)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+1.1344P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8723
_refine_ls_number_parameters     527
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0882
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.95882(4) 0.41000(3) 0.39912(3) 0.02512(10) Uani 1 1 d . . . . .
Cl2 Cl 0.35317(4) 0.38930(3) 1.41894(3) 0.02661(10) Uani 1 1 d . . . . .
S1 S 0.52874(4) 0.85551(3) 0.13290(2) 0.01282(8) Uani 1 1 d . . . . .
S2 S 0.00256(3) 0.85450(3) 1.12588(2) 0.01229(8) Uani 1 1 d . . . . .
O1 O 0.42864(11) 0.83775(8) 0.09492(7) 0.0187(2) Uani 1 1 d . . . . .
O2 O 0.47746(12) 0.89519(8) 0.22085(7) 0.0209(2) Uani 1 1 d . . . . .
O3 O 0.75783(12) 0.87720(9) -0.30992(7) 0.0222(2) Uani 1 1 d . . . . .
O4 O -0.02417(11) 0.86157(8) 1.03903(7) 0.0174(2) Uani 1 1 d . . . . .
O5 O -0.11294(10) 0.84776(8) 1.20748(7) 0.0170(2) Uani 1 1 d . . . . .
O6 O 0.23317(13) 0.85438(9) 0.68738(7) 0.0251(3) Uani 1 1 d . . . . .
N1 N 0.85916(13) 0.62769(10) 0.05406(8) 0.0161(3) Uani 1 1 d . . . . .
N2 N 0.31436(13) 0.60840(9) 1.06007(8) 0.0151(2) Uani 1 1 d . . . . .
C1 C 0.99833(16) 0.50381(11) 0.13354(10) 0.0170(3) Uani 1 1 d . . . . .
H1 H 1.061750 0.486629 0.075778 0.020 Uiso 1 1 calc R U . . .
C2 C 1.02223(16) 0.45314(11) 0.21378(11) 0.0177(3) Uani 1 1 d . . . . .
H2 H 1.102767 0.401732 0.212051 0.021 Uiso 1 1 calc R U . . .
C3 C 0.92619(16) 0.47802(11) 0.29891(10) 0.0168(3) Uani 1 1 d . . . . .
C4 C 0.81006(15) 0.55251(11) 0.30476(10) 0.0155(3) Uani 1 1 d . . . . .
H4 H 0.746506 0.566866 0.363217 0.019 Uiso 1 1 calc R U . . .
C5 C 0.67180(14) 0.69206(11) 0.22223(9) 0.0125(3) Uani 1 1 d . . . . .
C6 C 0.65599(14) 0.73943(11) 0.13775(10) 0.0127(3) Uani 1 1 d . . . . .
C7 C 0.75104(15) 0.70215(11) 0.05345(10) 0.0141(3) Uani 1 1 d . . . . .
C8 C 0.87930(15) 0.58184(11) 0.13626(10) 0.0142(3) Uani 1 1 d . . . . .
C9 C 0.78553(15) 0.60828(11) 0.22224(10) 0.0133(3) Uani 1 1 d . . . . .
C10 C 0.57716(14) 0.71999(11) 0.31398(9) 0.0134(3) Uani 1 1 d . . . . .
C11 C 0.60662(16) 0.78430(12) 0.36365(10) 0.0175(3) Uani 1 1 d . . . . .
H11 H 0.687133 0.813306 0.338679 0.021 Uiso 1 1 calc R U . . .
C12 C 0.51703(17) 0.80547(12) 0.44996(11) 0.0216(3) Uani 1 1 d . . . . .
H12 H 0.535368 0.850629 0.483436 0.026 Uiso 1 1 calc R U . . .
C13 C 0.40130(17) 0.76152(14) 0.48779(11) 0.0252(4) Uani 1 1 d . . . . .
H13 H 0.340625 0.776360 0.546956 0.030 Uiso 1 1 calc R U . . .
C14 C 0.37438(17) 0.69603(14) 0.43919(12) 0.0275(4) Uani 1 1 d . . . . .
H14 H 0.295629 0.665028 0.465254 0.033 Uiso 1 1 calc R U . . .
C15 C 0.46209(16) 0.67544(13) 0.35243(11) 0.0220(3) Uani 1 1 d . . . . .
H15 H 0.443061 0.630439 0.319146 0.026 Uiso 1 1 calc R U . . .
C16 C 0.62428(15) 0.94528(11) 0.05679(10) 0.0166(3) Uani 1 1 d . . . . .
H16A H 0.647714 0.929353 -0.006784 0.025 Uiso 1 1 calc R U . . .
H16B H 0.708798 0.940774 0.072521 0.025 Uiso 1 1 calc R U . . .
H16C H 0.569369 1.015530 0.062387 0.025 Uiso 1 1 calc R U . . .
C17 C 0.74376(15) 0.74664(11) -0.04140(10) 0.0148(3) Uani 1 1 d . . . . .
C18 C 0.86053(15) 0.78010(11) -0.10381(10) 0.0163(3) Uani 1 1 d . . . . .
H18 H 0.939817 0.773266 -0.084742 0.020 Uiso 1 1 calc R U . . .
C19 C 0.86236(16) 0.82290(12) -0.19264(10) 0.0170(3) Uani 1 1 d . . . . .
H19 H 0.942296 0.845410 -0.234032 0.020 Uiso 1 1 calc R U . . .
C20 C 0.74667(16) 0.83298(11) -0.22140(10) 0.0169(3) Uani 1 1 d . . . . .
C21 C 0.63133(16) 0.79736(12) -0.16109(10) 0.0179(3) Uani 1 1 d . . . . .
H21 H 0.552954 0.802776 -0.180784 0.021 Uiso 1 1 calc R U . . .
C22 C 0.63065(16) 0.75371(12) -0.07172(10) 0.0171(3) Uani 1 1 d . . . . .
H22 H 0.552101 0.728571 -0.031158 0.021 Uiso 1 1 calc R U . . .
C23 C 0.63762(18) 0.89813(14) -0.33914(11) 0.0242(3) Uani 1 1 d . . . . .
H23A H 0.657099 0.933869 -0.402040 0.036 Uiso 1 1 calc R U . . .
H23B H 0.563096 0.942126 -0.297384 0.036 Uiso 1 1 calc R U . . .
H23C H 0.610055 0.832774 -0.338073 0.036 Uiso 1 1 calc R U . . .
C24 C 0.41828(16) 0.46882(12) 1.14932(11) 0.0197(3) Uani 1 1 d . . . . .
H24 H 0.477953 0.442213 1.093909 0.024 Uiso 1 1 calc R U . . .
C25 C 0.42732(16) 0.41773(12) 1.23272(11) 0.0205(3) Uani 1 1 d . . . . .
H25 H 0.493521 0.355809 1.235544 0.025 Uiso 1 1 calc R U . . .
C26 C 0.33807(16) 0.45725(12) 1.31452(11) 0.0181(3) Uani 1 1 d . . . . .
C27 C 0.24518(15) 0.54831(11) 1.31402(10) 0.0153(3) Uani 1 1 d . . . . .
H27 H 0.188032 0.574251 1.370298 0.018 Uiso 1 1 calc R U . . .
C28 C 0.14519(14) 0.70116(11) 1.22115(10) 0.0122(3) Uani 1 1 d . . . . .
C29 C 0.13515(14) 0.74338(11) 1.13405(10) 0.0122(3) Uani 1 1 d . . . . .
C30 C 0.22454(14) 0.69511(11) 1.05372(10) 0.0128(3) Uani 1 1 d . . . . .
C31 C 0.31993(15) 0.56158(11) 1.14525(10) 0.0147(3) Uani 1 1 d . . . . .
C32 C 0.23562(14) 0.60339(11) 1.22800(10) 0.0133(3) Uani 1 1 d . . . . .
C33 C 0.08008(15) 0.75594(11) 1.30613(10) 0.0134(3) Uani 1 1 d . . . . .
C34 C -0.03329(15) 0.72933(11) 1.37729(10) 0.0168(3) Uani 1 1 d . . . . .
H34 H -0.076821 0.677426 1.371240 0.020 Uiso 1 1 calc R U . . .
C35 C -0.08215(16) 0.77875(12) 1.45669(10) 0.0200(3) Uani 1 1 d . . . . .
H35 H -0.159872 0.760996 1.504640 0.024 Uiso 1 1 calc R U . . .
C36 C -0.01861(17) 0.85397(12) 1.46684(11) 0.0210(3) Uani 1 1 d . . . . .
H36 H -0.052375 0.887230 1.521627 0.025 Uiso 1 1 calc R U . . .
C37 C 0.09423(17) 0.88029(12) 1.39675(11) 0.0216(3) Uani 1 1 d . . . . .
H37 H 0.137661 0.932036 1.403213 0.026 Uiso 1 1 calc R U . . .
C38 C 0.14402(16) 0.83090(12) 1.31679(10) 0.0174(3) Uani 1 1 d . . . . .
H38 H 0.222170 0.848504 1.269190 0.021 Uiso 1 1 calc R U . . .
C39 C 0.07137(16) 0.96251(11) 1.12661(11) 0.0179(3) Uani 1 1 d . . . . .
H39A H 0.167985 0.952609 1.089072 0.027 Uiso 1 1 calc R U . . .
H39B H 0.064726 0.969502 1.190165 0.027 Uiso 1 1 calc R U . . .
H39C H 0.019580 1.025372 1.101000 0.027 Uiso 1 1 calc R U . . .
C40 C 0.23062(14) 0.73868(11) 0.95651(10) 0.0136(3) Uani 1 1 d . . . . .
C41 C 0.26238(16) 0.83542(12) 0.92106(10) 0.0180(3) Uani 1 1 d . . . . .
H41 H 0.281262 0.874498 0.959479 0.022 Uiso 1 1 calc R U . . .
C42 C 0.26751(16) 0.87724(12) 0.83079(10) 0.0187(3) Uani 1 1 d . . . . .
H42 H 0.289838 0.943735 0.807686 0.022 Uiso 1 1 calc R U . . .
C43 C 0.23931(15) 0.81977(12) 0.77521(10) 0.0174(3) Uani 1 1 d . . . . .
C44 C 0.21415(16) 0.71984(12) 0.80816(10) 0.0195(3) Uani 1 1 d . . . . .
H44 H 0.199812 0.679324 0.768837 0.023 Uiso 1 1 calc R U . . .
C45 C 0.21008(15) 0.67973(12) 0.89801(10) 0.0169(3) Uani 1 1 d . . . . .
H45 H 0.193191 0.611599 0.920067 0.020 Uiso 1 1 calc R U . . .
C46 C 0.25675(19) 0.95691(13) 0.65017(11) 0.0279(4) Uani 1 1 d . . . . .
H46A H 0.349774 0.961439 0.647520 0.042 Uiso 1 1 calc R U . . .
H46B H 0.189584 1.007105 0.689727 0.042 Uiso 1 1 calc R U . . .
H46C H 0.247023 0.972306 0.587837 0.042 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 1.7388(15) . ?
Cl2 C26 1.7362(15) . ?
S1 O2 1.4347(11) . ?
S1 O1 1.4415(11) . ?
S1 C16 1.7658(15) . ?
S1 C6 1.7980(15) . ?
S2 O4 1.4393(10) . ?
S2 O5 1.4400(11) . ?
S2 C39 1.7659(15) . ?
S2 C29 1.7946(14) . ?
O3 C20 1.3652(18) . ?
O3 C23 1.4259(19) . ?
O6 C43 1.3676(18) . ?
O6 C46 1.433(2) . ?
N1 C7 1.3205(19) . ?
N1 C8 1.3642(18) . ?
N2 C30 1.3193(19) . ?
N2 C31 1.3627(19) . ?
C1 C2 1.368(2) . ?
C1 C8 1.418(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.408(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.367(2) . ?
C4 C9 1.422(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3855(19) . ?
C5 C9 1.429(2) . ?
C5 C10 1.4909(19) . ?
C6 C7 1.4430(19) . ?
C7 C17 1.4958(19) . ?
C8 C9 1.415(2) . ?
C10 C15 1.383(2) . ?
C10 C11 1.394(2) . ?
C11 C12 1.388(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C22 1.390(2) . ?
C17 C18 1.401(2) . ?
C18 C19 1.382(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.394(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.391(2) . ?
C21 C22 1.395(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.364(2) . ?
C24 C31 1.418(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.407(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.367(2) . ?
C27 C32 1.418(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.3875(19) . ?
C28 C32 1.430(2) . ?
C28 C33 1.4981(19) . ?
C29 C30 1.4393(19) . ?
C30 C40 1.4936(19) . ?
C31 C32 1.417(2) . ?
C33 C38 1.392(2) . ?
C33 C34 1.397(2) . ?
C34 C35 1.386(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.388(2) . ?
C35 H35 0.9500 . ?
C36 C37 1.385(2) . ?
C36 H36 0.9500 . ?
C37 C38 1.392(2) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 C41 1.383(2) . ?
C40 C45 1.396(2) . ?
C41 C42 1.392(2) . ?
C41 H41 0.9500 . ?
C42 C43 1.389(2) . ?
C42 H42 0.9500 . ?
C43 C44 1.396(2) . ?
C44 C45 1.383(2) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?

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 116.94(7) . . ?
O2 S1 C16 105.75(7) . . ?
O1 S1 C16 110.11(7) . . ?
O2 S1 C6 109.62(6) . . ?
O1 S1 C6 109.99(6) . . ?
C16 S1 C6 103.53(7) . . ?
O4 S2 O5 116.23(6) . . ?
O4 S2 C39 109.09(7) . . ?
O5 S2 C39 108.41(7) . . ?
O4 S2 C29 108.72(6) . . ?
O5 S2 C29 108.31(6) . . ?
C39 S2 C29 105.56(7) . . ?
C20 O3 C23 117.31(12) . . ?
C43 O6 C46 117.98(12) . . ?
C7 N1 C8 119.55(12) . . ?
C30 N2 C31 119.06(12) . . ?
C2 C1 C8 120.28(14) . . ?
C2 C1 H1 119.9 . . ?
C8 C1 H1 119.9 . . ?
C1 C2 C3 119.30(14) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 122.38(14) . . ?
C4 C3 Cl1 119.81(12) . . ?
C2 C3 Cl1 117.81(12) . . ?
C3 C4 C9 119.17(13) . . ?
C3 C4 H4 120.4 . . ?
C9 C4 H4 120.4 . . ?
C6 C5 C9 117.96(13) . . ?
C6 C5 C10 125.07(13) . . ?
C9 C5 C10 116.95(12) . . ?
C5 C6 C7 119.92(13) . . ?
C5 C6 S1 119.81(11) . . ?
C7 C6 S1 119.94(10) . . ?
N1 C7 C6 121.56(13) . . ?
N1 C7 C17 113.67(12) . . ?
C6 C7 C17 124.65(13) . . ?
N1 C8 C9 122.46(13) . . ?
N1 C8 C1 117.61(13) . . ?
C9 C8 C1 119.92(13) . . ?
C8 C9 C4 118.90(13) . . ?
C8 C9 C5 118.27(13) . . ?
C4 C9 C5 122.82(13) . . ?
C15 C10 C11 119.78(14) . . ?
C15 C10 C5 118.52(13) . . ?
C11 C10 C5 121.58(13) . . ?
C12 C11 C10 119.28(14) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C13 C12 C11 120.72(15) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 119.71(15) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.07(16) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C10 C15 C14 120.41(15) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
S1 C16 H16A 109.5 . . ?
S1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
S1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C17 C18 118.53(13) . . ?
C22 C17 C7 124.14(13) . . ?
C18 C17 C7 117.30(13) . . ?
C19 C18 C17 121.13(14) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 119.89(14) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
O3 C20 C21 124.77(14) . . ?
O3 C20 C19 115.57(13) . . ?
C21 C20 C19 119.65(14) . . ?
C20 C21 C22 120.07(14) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 120.66(14) . . ?
C17 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C31 120.08(14) . . ?
C25 C24 H24 120.0 . . ?
C31 C24 H24 120.0 . . ?
C24 C25 C26 119.66(14) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C27 C26 C25 122.33(14) . . ?
C27 C26 Cl2 119.66(12) . . ?
C25 C26 Cl2 117.95(12) . . ?
C26 C27 C32 118.83(14) . . ?
C26 C27 H27 120.6 . . ?
C32 C27 H27 120.6 . . ?
C29 C28 C32 117.36(13) . . ?
C29 C28 C33 124.44(13) . . ?
C32 C28 C33 117.86(12) . . ?
C28 C29 C30 120.21(13) . . ?
C28 C29 S2 118.09(11) . . ?
C30 C29 S2 121.61(10) . . ?
N2 C30 C29 121.88(13) . . ?
N2 C30 C40 113.47(12) . . ?
C29 C30 C40 124.60(13) . . ?
N2 C31 C32 122.86(13) . . ?
N2 C31 C24 117.46(13) . . ?
C32 C31 C24 119.64(13) . . ?
C31 C32 C27 119.31(13) . . ?
C31 C32 C28 118.23(13) . . ?
C27 C32 C28 122.44(13) . . ?
C38 C33 C34 119.28(13) . . ?
C38 C33 C28 117.32(13) . . ?
C34 C33 C28 123.18(13) . . ?
C35 C34 C33 119.92(14) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C34 C35 C36 120.63(14) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C37 C36 C35 119.71(14) . . ?
C37 C36 H36 120.1 . . ?
C35 C36 H36 120.1 . . ?
C36 C37 C38 120.00(15) . . ?
C36 C37 H37 120.0 . . ?
C38 C37 H37 120.0 . . ?
C33 C38 C37 120.45(14) . . ?
C33 C38 H38 119.8 . . ?
C37 C38 H38 119.8 . . ?
S2 C39 H39A 109.5 . . ?
S2 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
S2 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C41 C40 C45 118.48(13) . . ?
C41 C40 C30 121.39(13) . . ?
C45 C40 C30 120.07(13) . . ?
C40 C41 C42 121.98(14) . . ?
C40 C41 H41 119.0 . . ?
C42 C41 H41 119.0 . . ?
C43 C42 C41 118.64(14) . . ?
C43 C42 H42 120.7 . . ?
C41 C42 H42 120.7 . . ?
O6 C43 C42 124.34(14) . . ?
O6 C43 C44 115.49(13) . . ?
C42 C43 C44 120.18(14) . . ?
C45 C44 C43 120.08(14) . . ?
C45 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?
C44 C45 C40 120.46(14) . . ?
C44 C45 H45 119.8 . . ?
C40 C45 H45 119.8 . . ?
O6 C46 H46A 109.5 . . ?
O6 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
O6 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?

_refine_diff_density_max         0.430
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_i17706
_database_code_depnum_ccdc_archive 'CCDC 1951573'
loop_
_audit_author_name
_audit_author_address
'Chieh-Kai Chan' 'Academia Sinica'
_audit_update_record             
;
2019-09-05 deposited with the CCDC.	2019-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 Cl N O2 S'
_chemical_formula_sum            'C23 H18 Cl N O2 S'
_chemical_formula_weight         407.89

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.2987(11)
_cell_length_b                   12.768(3)
_cell_length_c                   14.845(3)
_cell_angle_alpha                88.429(5)
_cell_angle_beta                 82.358(6)
_cell_angle_gamma                86.330(6)
_cell_volume                     993.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    4939
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      26.97

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.534
_exptl_crystal_size_mid          0.394
_exptl_crystal_size_min          0.118
_exptl_absorpt_coefficient_mu    0.316
_shelx_estimated_absorpt_T_min   0.849
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8255
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25425
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_av_R_equivalents  0.0819
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.598
_diffrn_reflns_theta_max         27.090
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4363
_reflns_number_gt                3366
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 740)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0420P)²+0.4667P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4363
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1102
_refine_ls_wR_factor_gt          0.1000
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.23015(15) 0.42130(5) 0.90169(4) 0.0461(2) Uani 1 1 d . . . . .
S1 S 0.99413(9) 0.87357(4) 0.63247(3) 0.01498(13) Uani 1 1 d . . . . .
O1 O 1.0798(3) 0.89233(11) 0.71763(9) 0.0240(3) Uani 1 1 d . . . . .
O2 O 1.1831(3) 0.87039(11) 0.55378(10) 0.0243(3) Uani 1 1 d . . . . .
N1 N 0.6347(3) 0.62709(13) 0.55944(11) 0.0185(4) Uani 1 1 d . . . . .
C1 C 0.3720(4) 0.50214(16) 0.64073(15) 0.0229(5) Uani 1 1 d . . . . .
H1 H 0.329392 0.479165 0.584628 0.028 Uiso 1 1 calc R U . . .
C2 C 0.2746(4) 0.45507(16) 0.71975(15) 0.0260(5) Uani 1 1 d . . . . .
H2 H 0.160277 0.400780 0.719275 0.031 Uiso 1 1 calc R U . . .
C3 C 0.3446(4) 0.48751(16) 0.80252(15) 0.0262(5) Uani 1 1 d . . . . .
C4 C 0.4965(4) 0.56900(15) 0.80638(14) 0.0210(4) Uani 1 1 d . . . . .
H4 H 0.538792 0.590104 0.863110 0.025 Uiso 1 1 calc R U . . .
C5 C 0.7318(4) 0.71382(14) 0.72367(13) 0.0146(4) Uani 1 1 d . . . . .
C6 C 0.8304(4) 0.75429(15) 0.63985(13) 0.0155(4) Uani 1 1 d . . . . .
C7 C 0.7816(4) 0.70650(15) 0.55767(13) 0.0153(4) Uani 1 1 d . . . . .
C8 C 0.5364(4) 0.58515(15) 0.64126(13) 0.0176(4) Uani 1 1 d . . . . .
C9 C 0.5908(4) 0.62198(14) 0.72485(13) 0.0162(4) Uani 1 1 d . . . . .
C10 C 0.7429(4) 0.76258(14) 0.81333(13) 0.0152(4) Uani 1 1 d . . . . .
C11 C 0.9327(4) 0.73160(16) 0.86596(14) 0.0213(4) Uani 1 1 d . . . . .
H11 H 1.063195 0.680657 0.843904 0.026 Uiso 1 1 calc R U . . .
C12 C 0.9328(4) 0.77458(17) 0.95057(14) 0.0245(5) Uani 1 1 d . . . . .
H12 H 1.064558 0.753791 0.986114 0.029 Uiso 1 1 calc R U . . .
C13 C 0.7413(4) 0.84777(18) 0.98334(14) 0.0272(5) Uani 1 1 d . . . . .
H13 H 0.741732 0.877540 1.041270 0.033 Uiso 1 1 calc R U . . .
C14 C 0.5493(4) 0.87753(17) 0.93175(15) 0.0264(5) Uani 1 1 d . . . . .
H14 H 0.417055 0.927384 0.954561 0.032 Uiso 1 1 calc R U . . .
C15 C 0.5486(4) 0.83502(16) 0.84676(14) 0.0196(4) Uani 1 1 d . . . . .
H15 H 0.415709 0.855369 0.811592 0.024 Uiso 1 1 calc R U . . .
C16 C 0.7494(4) 0.96790(15) 0.61559(14) 0.0217(5) Uani 1 1 d . . . . .
H16A H 0.818745 1.037406 0.608117 0.033 Uiso 1 1 calc R U . . .
H16B H 0.616757 0.967666 0.668320 0.033 Uiso 1 1 calc R U . . .
H16C H 0.675663 0.951442 0.560893 0.033 Uiso 1 1 calc R U . . .
C17 C 0.8810(4) 0.74253(15) 0.46339(13) 0.0154(4) Uani 1 1 d . . . . .
C18 C 0.7299(4) 0.80932(15) 0.41485(13) 0.0184(4) Uani 1 1 d . . . . .
H18 H 0.566616 0.835057 0.442584 0.022 Uiso 1 1 calc R U . . .
C19 C 0.8158(4) 0.83884(16) 0.32594(13) 0.0201(4) Uani 1 1 d . . . . .
H19 H 0.710238 0.884971 0.293700 0.024 Uiso 1 1 calc R U . . .
C20 C 1.0529(4) 0.80231(16) 0.28315(13) 0.0188(4) Uani 1 1 d . . . . .
C21 C 1.2002(4) 0.73367(16) 0.33181(14) 0.0213(4) Uani 1 1 d . . . . .
H21 H 1.361625 0.706530 0.303510 0.026 Uiso 1 1 calc R U . . .
C22 C 1.1172(4) 0.70381(16) 0.42076(14) 0.0207(4) Uani 1 1 d . . . . .
H22 H 1.221651 0.656841 0.452695 0.025 Uiso 1 1 calc R U . . .
C23 C 1.1482(5) 0.83602(19) 0.18725(14) 0.0304(5) Uani 1 1 d . . . . .
H23A H 1.051754 0.803157 0.144885 0.046 Uiso 1 1 calc R U . . .
H23B H 1.329670 0.814289 0.173252 0.046 Uiso 1 1 calc R U . . .
H23C H 1.125286 0.912552 0.181245 0.046 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 1.735(2) . ?
S1 O1 1.4300(14) . ?
S1 O2 1.4336(15) . ?
S1 C16 1.751(2) . ?
S1 C6 1.794(2) . ?
N1 C7 1.315(2) . ?
N1 C8 1.366(2) . ?
C1 C2 1.358(3) . ?
C1 C8 1.415(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.410(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.363(3) . ?
C4 C9 1.418(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(3) . ?
C5 C9 1.429(3) . ?
C5 C10 1.495(3) . ?
C6 C7 1.440(3) . ?
C7 C17 1.499(3) . ?
C8 C9 1.410(3) . ?
C10 C11 1.385(3) . ?
C10 C15 1.389(3) . ?
C11 C12 1.385(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.386(3) . ?
C17 C22 1.392(3) . ?
C18 C19 1.388(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(3) . ?
C20 C23 1.507(3) . ?
C21 C22 1.386(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 116.95(9) . . ?
O1 S1 C16 108.51(10) . . ?
O2 S1 C16 109.66(10) . . ?
O1 S1 C6 109.81(9) . . ?
O2 S1 C6 108.88(9) . . ?
C16 S1 C6 101.99(10) . . ?
C7 N1 C8 119.32(17) . . ?
C2 C1 C8 120.55(19) . . ?
C2 C1 H1 119.7 . . ?
C8 C1 H1 119.7 . . ?
C1 C2 C3 119.39(19) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 121.9(2) . . ?
C4 C3 Cl1 119.77(17) . . ?
C2 C3 Cl1 118.29(16) . . ?
C3 C4 C9 119.31(19) . . ?
C3 C4 H4 120.3 . . ?
C9 C4 H4 120.3 . . ?
C6 C5 C9 117.63(17) . . ?
C6 C5 C10 125.49(17) . . ?
C9 C5 C10 116.70(16) . . ?
C5 C6 C7 120.14(17) . . ?
C5 C6 S1 120.27(14) . . ?
C7 C6 S1 119.33(14) . . ?
N1 C7 C6 121.67(17) . . ?
N1 C7 C17 113.46(16) . . ?
C6 C7 C17 124.84(17) . . ?
N1 C8 C9 122.61(18) . . ?
N1 C8 C1 117.81(18) . . ?
C9 C8 C1 119.58(18) . . ?
C8 C9 C4 119.00(18) . . ?
C8 C9 C5 118.18(17) . . ?
C4 C9 C5 122.79(18) . . ?
C11 C10 C15 119.73(18) . . ?
C11 C10 C5 121.25(17) . . ?
C15 C10 C5 118.87(17) . . ?
C12 C11 C10 120.26(19) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 120.0(2) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 119.9(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.4(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 119.7(2) . . ?
C14 C15 H15 120.1 . . ?
C10 C15 H15 120.1 . . ?
S1 C16 H16A 109.5 . . ?
S1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
S1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 118.87(18) . . ?
C18 C17 C7 120.07(17) . . ?
C22 C17 C7 120.89(17) . . ?
C17 C18 C19 120.37(19) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C20 121.35(19) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C21 C20 C19 117.75(18) . . ?
C21 C20 C23 120.91(19) . . ?
C19 C20 C23 121.34(19) . . ?
C22 C21 C20 121.50(19) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C17 120.13(19) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_i17722
_database_code_depnum_ccdc_archive 'CCDC 1954575'
loop_
_audit_author_name
_audit_author_address
'Chieh-Kai Chan' 'Academia Sinica'
_audit_update_record             
;
2019-09-19 deposited with the CCDC.	2019-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H18 Cl N O'
_chemical_formula_sum            'C28 H18 Cl N O'
_chemical_formula_weight         419.88

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6174(7)
_cell_length_b                   10.1886(7)
_cell_length_c                   11.7888(9)
_cell_angle_alpha                95.003(2)
_cell_angle_beta                 107.482(2)
_cell_angle_gamma                111.455(2)
_cell_volume                     999.86(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9890
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      27.1

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_F_000             436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.436
_exptl_crystal_size_mid          0.277
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.213
_shelx_estimated_absorpt_T_min   0.913
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9595
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33249
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.857
_diffrn_reflns_theta_max         27.125
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4417
_reflns_number_gt                3832
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 740)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0342P)²+0.5930P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4417
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0864
_refine_ls_wR_factor_gt          0.0810
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.91784(4) 0.17916(3) 0.22979(3) 0.01934(9) Uani 1 1 d . . . . .
O1 O 0.72835(11) 0.92346(9) 0.46729(8) 0.0170(2) Uani 1 1 d . . . . .
N1 N 0.73967(12) 0.53334(11) 0.53326(9) 0.0128(2) Uani 1 1 d . . . . .
C1 C 0.79985(15) 0.33071(14) 0.49271(12) 0.0149(3) Uani 1 1 d . . . . .
H1 H 0.783999 0.304696 0.564759 0.018 Uiso 1 1 calc R U . . .
C2 C 0.83973(15) 0.24698(13) 0.42248(12) 0.0154(3) Uani 1 1 d . . . . .
H2 H 0.849916 0.162604 0.444662 0.018 Uiso 1 1 calc R U . . .
C3 C 0.86545(15) 0.28723(14) 0.31710(12) 0.0146(3) Uani 1 1 d . . . . .
C4 C 0.85203(15) 0.40783(13) 0.28173(11) 0.0138(2) Uani 1 1 d . . . . .
H4 H 0.871603 0.433064 0.210564 0.017 Uiso 1 1 calc R U . . .
C5 C 0.79180(14) 0.62205(13) 0.32264(11) 0.0124(2) Uani 1 1 d . . . . .
C6 C 0.71206(16) 0.82603(13) 0.36248(11) 0.0142(3) Uani 1 1 d . . . . .
H6 H 0.795243 0.881494 0.329814 0.017 Uiso 1 1 calc R U . . .
C7 C 0.62959(16) 0.94901(14) 0.62376(12) 0.0172(3) Uani 1 1 d . . . . .
H7 H 0.631025 1.038728 0.606436 0.021 Uiso 1 1 calc R U . . .
C8 C 0.58346(16) 0.90049(15) 0.71837(12) 0.0182(3) Uani 1 1 d . . . . .
H8 H 0.553284 0.957287 0.766284 0.022 Uiso 1 1 calc R U . . .
C9 C 0.58110(16) 0.76879(15) 0.74361(12) 0.0177(3) Uani 1 1 d . . . . .
H9 H 0.549431 0.735946 0.808625 0.021 Uiso 1 1 calc R U . . .
C10 C 0.62505(15) 0.68566(14) 0.67371(11) 0.0146(3) Uani 1 1 d . . . . .
H10 H 0.623463 0.596046 0.691410 0.018 Uiso 1 1 calc R U . . .
C11 C 0.78172(14) 0.45574(13) 0.45993(11) 0.0126(2) Uani 1 1 d . . . . .
C12 C 0.80845(14) 0.49466(13) 0.35286(11) 0.0121(2) Uani 1 1 d . . . . .
C13 C 0.74561(15) 0.69710(13) 0.39602(11) 0.0126(2) Uani 1 1 d . . . . .
C14 C 0.67375(15) 0.86510(13) 0.55443(11) 0.0139(2) Uani 1 1 d . . . . .
C15 C 0.67173(15) 0.73224(13) 0.57735(11) 0.0131(2) Uani 1 1 d . . . . .
C16 C 0.72066(14) 0.64863(13) 0.50118(11) 0.0124(2) Uani 1 1 d . . . . .
C17 C 0.82271(15) 0.67118(13) 0.21347(11) 0.0137(3) Uani 1 1 d . . . . .
C18 C 0.72106(16) 0.59058(14) 0.09621(12) 0.0174(3) Uani 1 1 d . . . . .
H18 H 0.632997 0.502186 0.085543 0.021 Uiso 1 1 calc R U . . .
C19 C 0.74779(18) 0.63874(16) -0.00494(13) 0.0219(3) Uani 1 1 d . . . . .
H19 H 0.678278 0.583096 -0.084572 0.026 Uiso 1 1 calc R U . . .
C20 C 0.87576(18) 0.76795(17) 0.00985(13) 0.0237(3) Uani 1 1 d . . . . .
H20 H 0.892727 0.801430 -0.059642 0.028 Uiso 1 1 calc R U . . .
C21 C 0.97889(17) 0.84825(16) 0.12591(14) 0.0220(3) Uani 1 1 d . . . . .
H21 H 1.067156 0.936258 0.136023 0.026 Uiso 1 1 calc R U . . .
C22 C 0.95291(16) 0.79970(14) 0.22767(12) 0.0171(3) Uani 1 1 d . . . . .
H22 H 1.024213 0.854373 0.307180 0.020 Uiso 1 1 calc R U . . .
C23 C 0.55040(16) 0.78201(14) 0.26200(12) 0.0152(3) Uani 1 1 d . . . . .
C24 C 0.40814(17) 0.69894(14) 0.27724(12) 0.0185(3) Uani 1 1 d . . . . .
H24 H 0.411299 0.665512 0.350334 0.022 Uiso 1 1 calc R U . . .
C25 C 0.26160(18) 0.66500(16) 0.18547(13) 0.0241(3) Uani 1 1 d . . . . .
H25 H 0.164943 0.609859 0.196731 0.029 Uiso 1 1 calc R U . . .
C26 C 0.25618(19) 0.71140(17) 0.07761(13) 0.0260(3) Uani 1 1 d . . . . .
H26 H 0.155961 0.688905 0.015523 0.031 Uiso 1 1 calc R U . . .
C27 C 0.39685(19) 0.79042(16) 0.06060(13) 0.0245(3) Uani 1 1 d . . . . .
H27 H 0.393236 0.820186 -0.013996 0.029 Uiso 1 1 calc R U . . .
C28 C 0.54362(18) 0.82637(15) 0.15256(12) 0.0197(3) Uani 1 1 d . . . . .
H28 H 0.639870 0.881507 0.140753 0.024 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 1.7452(13) . ?
O1 C14 1.3736(15) . ?
O1 C6 1.4466(15) . ?
N1 C16 1.3226(16) . ?
N1 C11 1.3641(16) . ?
C1 C2 1.3665(18) . ?
C1 C11 1.4179(17) . ?
C1 H1 0.9500 . ?
C2 C3 1.4042(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3687(18) . ?
C4 C12 1.4193(17) . ?
C4 H4 0.9500 . ?
C5 C13 1.3763(17) . ?
C5 C12 1.4268(17) . ?
C5 C17 1.4928(17) . ?
C6 C13 1.5199(17) . ?
C6 C23 1.5207(18) . ?
C6 H6 1.0000 . ?
C7 C8 1.3850(19) . ?
C7 C14 1.3898(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.3932(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.3873(18) . ?
C9 H9 0.9500 . ?
C10 C15 1.4005(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.4227(17) . ?
C13 C16 1.4272(17) . ?
C14 C15 1.3977(18) . ?
C15 C16 1.4722(17) . ?
C17 C18 1.3943(18) . ?
C17 C22 1.3953(18) . ?
C18 C19 1.3865(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.387(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.3927(19) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C28 1.3949(18) . ?
C23 C24 1.3955(19) . ?
C24 C25 1.392(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.388(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.383(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.391(2) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O1 C6 118.34(9) . . ?
C16 N1 C11 117.79(11) . . ?
C2 C1 C11 121.16(12) . . ?
C2 C1 H1 119.4 . . ?
C11 C1 H1 119.4 . . ?
C1 C2 C3 119.16(12) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 122.37(12) . . ?
C4 C3 Cl1 119.43(10) . . ?
C2 C3 Cl1 118.20(10) . . ?
C3 C4 C12 119.07(12) . . ?
C3 C4 H4 120.5 . . ?
C12 C4 H4 120.5 . . ?
C13 C5 C12 118.30(11) . . ?
C13 C5 C17 121.24(11) . . ?
C12 C5 C17 120.46(11) . . ?
O1 C6 C13 112.40(10) . . ?
O1 C6 C23 110.72(10) . . ?
C13 C6 C23 112.80(10) . . ?
O1 C6 H6 106.8 . . ?
C13 C6 H6 106.8 . . ?
C23 C6 H6 106.8 . . ?
C8 C7 C14 119.32(12) . . ?
C8 C7 H7 120.3 . . ?
C14 C7 H7 120.3 . . ?
C7 C8 C9 120.32(12) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 119.92(12) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C15 120.82(12) . . ?
C9 C10 H10 119.6 . . ?
C15 C10 H10 119.6 . . ?
N1 C11 C1 118.11(11) . . ?
N1 C11 C12 123.12(11) . . ?
C1 C11 C12 118.77(11) . . ?
C4 C12 C11 119.46(11) . . ?
C4 C12 C5 122.75(11) . . ?
C11 C12 C5 117.78(11) . . ?
C5 C13 C16 119.61(11) . . ?
C5 C13 C6 120.69(11) . . ?
C16 C13 C6 119.61(11) . . ?
O1 C14 C7 116.50(11) . . ?
O1 C14 C15 121.83(11) . . ?
C7 C14 C15 121.56(12) . . ?
C14 C15 C10 118.06(12) . . ?
C14 C15 C16 119.04(11) . . ?
C10 C15 C16 122.89(11) . . ?
N1 C16 C13 123.34(11) . . ?
N1 C16 C15 118.81(11) . . ?
C13 C16 C15 117.86(11) . . ?
C18 C17 C22 119.14(12) . . ?
C18 C17 C5 120.60(11) . . ?
C22 C17 C5 120.25(11) . . ?
C19 C18 C17 120.36(13) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 120.17(13) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 120.07(13) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 119.88(13) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C21 C22 C17 120.36(13) . . ?
C21 C22 H22 119.8 . . ?
C17 C22 H22 119.8 . . ?
C28 C23 C24 119.15(13) . . ?
C28 C23 C6 119.48(12) . . ?
C24 C23 C6 121.37(12) . . ?
C25 C24 C23 120.09(13) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C26 C25 C24 120.26(14) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C27 C26 C25 119.92(14) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C28 120.11(13) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C27 C28 C23 120.44(14) . . ?
C27 C28 H28 119.8 . . ?
C23 C28 H28 119.8 . . ?

_refine_diff_density_max         0.336
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_i17681
_database_code_depnum_ccdc_archive 'CCDC 1943320'
loop_
_audit_author_name
_audit_author_address
'Chieh-Kai Chan' 'Academia Sinica'
_audit_update_record             
;
2019-07-26 deposited with the CCDC.	2019-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H22 Cl N O2 S'
_chemical_formula_sum            'C29 H22 Cl N O2 S'
_chemical_formula_weight         483.98

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   16.3487(18)
_cell_length_b                   9.1325(10)
_cell_length_c                   16.747(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.046(3)
_cell_angle_gamma                90
_cell_volume                     2403.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9600
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      27.11

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.558
_exptl_crystal_size_mid          0.492
_exptl_crystal_size_min          0.343
_exptl_absorpt_coefficient_mu    0.273
_shelx_estimated_absorpt_T_min   0.862
_shelx_estimated_absorpt_T_max   0.912
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9559
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            60495
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.046
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5299
_reflns_number_gt                4674
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 740)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²+1.6570P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5299
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0905
_refine_ls_wR_factor_gt          0.0853
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.32678(2) 0.21340(5) 0.51029(3) 0.03105(11) Uani 1 1 d . . . . .
S1 S 0.82323(2) 0.31425(4) 0.56837(2) 0.01546(9) Uani 1 1 d . . . . .
O1 O 0.86284(6) 0.45670(12) 0.58206(6) 0.0217(2) Uani 1 1 d . . . . .
O2 O 0.82668(7) 0.22360(13) 0.63975(6) 0.0231(2) Uani 1 1 d . . . . .
N1 N 0.61277(7) 0.35914(13) 0.37457(7) 0.0179(2) Uani 1 1 d . . . . .
C1 C 0.69159(9) 0.36989(15) 0.42263(8) 0.0160(3) Uani 1 1 d . . . . .
C2 C 0.71313(8) 0.33450(15) 0.51007(8) 0.0145(3) Uani 1 1 d . . . . .
C3 C 0.64900(9) 0.30313(14) 0.54716(8) 0.0151(3) Uani 1 1 d . . . . .
C4 C 0.49208(9) 0.27004(16) 0.52659(9) 0.0192(3) Uani 1 1 d . . . . .
H4 H 0.499460 0.261602 0.584701 0.023 Uiso 1 1 calc R U . . .
C5 C 0.41333(9) 0.25377(16) 0.47194(9) 0.0202(3) Uani 1 1 d . . . . .
C6 C 0.39893(9) 0.26763(16) 0.38516(9) 0.0199(3) Uani 1 1 d . . . . .
H6 H 0.343790 0.252131 0.348598 0.024 Uiso 1 1 calc R U . . .
C7 C 0.46593(9) 0.30387(16) 0.35452(9) 0.0198(3) Uani 1 1 d . . . . .
H7 H 0.456625 0.317291 0.296435 0.024 Uiso 1 1 calc R U . . .
C8 C 0.54886(9) 0.32144(15) 0.40872(9) 0.0168(3) Uani 1 1 d . . . . .
C9 C 0.56297(9) 0.29983(15) 0.49526(9) 0.0162(3) Uani 1 1 d . . . . .
C10 C 0.75460(8) 0.41268(16) 0.37704(8) 0.0165(3) Uani 1 1 d . . . . .
C11 C 0.75857(9) 0.32816(16) 0.30875(9) 0.0189(3) Uani 1 1 d . . . . .
H11 H 0.721734 0.246407 0.292824 0.023 Uiso 1 1 calc R U . . .
C12 C 0.81578(9) 0.36238(17) 0.26390(9) 0.0215(3) Uani 1 1 d . . . . .
H12 H 0.818605 0.302366 0.218399 0.026 Uiso 1 1 calc R U . . .
C13 C 0.86925(9) 0.48387(17) 0.28479(9) 0.0221(3) Uani 1 1 d . . . . .
C14 C 0.86288(9) 0.57050(16) 0.35121(10) 0.0224(3) Uani 1 1 d . . . . .
H14 H 0.897738 0.655066 0.365283 0.027 Uiso 1 1 calc R U . . .
C15 C 0.80664(9) 0.53614(16) 0.39751(9) 0.0191(3) Uani 1 1 d . . . . .
H15 H 0.803675 0.596449 0.442842 0.023 Uiso 1 1 calc R U . . .
C16 C 0.93282(11) 0.5186(2) 0.23699(12) 0.0344(4) Uani 1 1 d . . . . .
H16A H 0.964711 0.429859 0.231880 0.052 Uiso 1 1 calc R U . . .
H16B H 0.972316 0.594032 0.266575 0.052 Uiso 1 1 calc R U . . .
H16C H 0.902669 0.554385 0.181490 0.052 Uiso 1 1 calc R U . . .
C17 C 0.86876(8) 0.21424(15) 0.50100(8) 0.0151(3) Uani 1 1 d . . . . .
C18 C 0.83507(9) 0.07817(16) 0.47170(9) 0.0189(3) Uani 1 1 d . . . . .
H18 H 0.789332 0.037510 0.489110 0.023 Uiso 1 1 calc R U . . .
C19 C 0.86947(9) 0.00303(16) 0.41662(9) 0.0214(3) Uani 1 1 d . . . . .
H19 H 0.846351 -0.089175 0.395576 0.026 Uiso 1 1 calc R U . . .
C20 C 0.93778(9) 0.06105(17) 0.39156(9) 0.0198(3) Uani 1 1 d . . . . .
C21 C 0.97219(9) 0.19510(16) 0.42435(9) 0.0188(3) Uani 1 1 d . . . . .
H21 H 1.019860 0.233731 0.409392 0.023 Uiso 1 1 calc R U . . .
C22 C 0.93763(9) 0.27311(16) 0.47874(8) 0.0166(3) Uani 1 1 d . . . . .
H22 H 0.960792 0.365044 0.500229 0.020 Uiso 1 1 calc R U . . .
C23 C 0.97223(11) -0.01834(19) 0.32860(10) 0.0277(3) Uani 1 1 d . . . . .
H23A H 0.926111 -0.034612 0.277771 0.041 Uiso 1 1 calc R U . . .
H23B H 0.996016 -0.112811 0.351514 0.041 Uiso 1 1 calc R U . . .
H23C H 1.016898 0.040925 0.315683 0.041 Uiso 1 1 calc R U . . .
C24 C 0.66084(8) 0.27212(15) 0.63720(8) 0.0148(3) Uani 1 1 d . . . . .
C25 C 0.67841(9) 0.38592(15) 0.69460(9) 0.0170(3) Uani 1 1 d . . . . .
H25 H 0.690152 0.481120 0.677742 0.020 Uiso 1 1 calc R U . . .
C26 C 0.67884(9) 0.36068(17) 0.77688(9) 0.0197(3) Uani 1 1 d . . . . .
H26 H 0.690202 0.438805 0.815849 0.024 Uiso 1 1 calc R U . . .
C27 C 0.66260(9) 0.22089(17) 0.80172(9) 0.0196(3) Uani 1 1 d . . . . .
H27 H 0.662571 0.203638 0.857657 0.023 Uiso 1 1 calc R U . . .
C28 C 0.64638(9) 0.10624(16) 0.74475(9) 0.0189(3) Uani 1 1 d . . . . .
H28 H 0.636549 0.010405 0.762128 0.023 Uiso 1 1 calc R U . . .
C29 C 0.64455(9) 0.13176(16) 0.66252(9) 0.0180(3) Uani 1 1 d . . . . .
H29 H 0.632228 0.053821 0.623446 0.022 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 C5 1.7473(15) . ?
S1 O2 1.4423(11) . ?
S1 O1 1.4431(11) . ?
S1 C17 1.7678(14) . ?
S1 C2 1.8044(14) . ?
N1 C1 1.3208(18) . ?
N1 C8 1.3666(18) . ?
C1 C2 1.4450(18) . ?
C1 C10 1.4937(18) . ?
C2 C3 1.3881(19) . ?
C3 C9 1.4349(19) . ?
C3 C24 1.4932(18) . ?
C4 C5 1.366(2) . ?
C4 C9 1.4244(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.412(2) . ?
C6 C7 1.372(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.417(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.4169(19) . ?
C10 C11 1.396(2) . ?
C10 C15 1.397(2) . ?
C11 C12 1.387(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.396(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(2) . ?
C13 C16 1.510(2) . ?
C14 C15 1.393(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C22 1.3885(19) . ?
C17 C18 1.393(2) . ?
C18 C19 1.387(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.401(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.395(2) . ?
C20 C23 1.511(2) . ?
C21 C22 1.3932(19) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.3908(19) . ?
C24 C29 1.3987(19) . ?
C25 C26 1.3951(19) . ?
C25 H25 0.9500 . ?
C26 C27 1.391(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.392(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.3887(19) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 118.21(7) . . ?
O2 S1 C17 107.79(7) . . ?
O1 S1 C17 108.51(6) . . ?
O2 S1 C2 108.17(6) . . ?
O1 S1 C2 109.29(6) . . ?
C17 S1 C2 103.93(6) . . ?
C1 N1 C8 119.59(12) . . ?
N1 C1 C2 121.62(12) . . ?
N1 C1 C10 113.74(12) . . ?
C2 C1 C10 124.55(12) . . ?
C3 C2 C1 119.80(12) . . ?
C3 C2 S1 120.04(10) . . ?
C1 C2 S1 119.90(10) . . ?
C2 C3 C9 117.93(12) . . ?
C2 C3 C24 126.00(12) . . ?
C9 C3 C24 116.07(12) . . ?
C5 C4 C9 119.08(13) . . ?
C5 C4 H4 120.5 . . ?
C9 C4 H4 120.5 . . ?
C4 C5 C6 122.54(13) . . ?
C4 C5 Cl1 119.06(12) . . ?
C6 C5 Cl1 118.40(11) . . ?
C7 C6 C5 118.89(13) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C6 C7 C8 120.60(13) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
N1 C8 C9 122.41(13) . . ?
N1 C8 C7 117.86(13) . . ?
C9 C8 C7 119.73(13) . . ?
C8 C9 C4 118.98(13) . . ?
C8 C9 C3 118.15(12) . . ?
C4 C9 C3 122.82(13) . . ?
C11 C10 C15 118.95(13) . . ?
C11 C10 C1 117.96(13) . . ?
C15 C10 C1 123.03(13) . . ?
C12 C11 C10 120.66(14) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.83(14) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 118.16(13) . . ?
C14 C13 C16 121.24(15) . . ?
C12 C13 C16 120.59(15) . . ?
C13 C14 C15 121.57(14) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C14 C15 C10 119.76(14) . . ?
C14 C15 H15 120.1 . . ?
C10 C15 H15 120.1 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C17 C18 121.47(13) . . ?
C22 C17 S1 119.15(11) . . ?
C18 C17 S1 119.38(11) . . ?
C19 C18 C17 118.83(13) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C18 C19 C20 121.02(14) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C21 C20 C19 118.82(13) . . ?
C21 C20 C23 120.55(14) . . ?
C19 C20 C23 120.62(14) . . ?
C22 C21 C20 120.92(13) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C17 C22 C21 118.89(13) . . ?
C17 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C29 119.70(12) . . ?
C25 C24 C3 120.04(12) . . ?
C29 C24 C3 119.84(12) . . ?
C24 C25 C26 120.20(13) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C27 C26 C25 119.86(13) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C26 C27 C28 120.09(13) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C29 C28 C27 120.09(13) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C24 120.05(13) . . ?
C28 C29 H29 120.0 . . ?
C24 C29 H29 120.0 . . ?

_refine_diff_density_max         0.372
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_i17657
_database_code_depnum_ccdc_archive 'CCDC 1940046'
loop_
_audit_author_name
_audit_author_address
'Chieh-Kai Chan' 'Academia Sinica'
_audit_update_record             
;
2019-07-12 deposited with the CCDC.	2019-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H20 Cl N O2 S'
_chemical_formula_sum            'C28 H20 Cl N O2 S'
_chemical_formula_weight         469.96

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   10.2889(9)
_cell_length_b                   15.5258(12)
_cell_length_c                   14.8833(12)
_cell_angle_alpha                90
_cell_angle_beta                 108.961(2)
_cell_angle_gamma                90
_cell_volume                     2248.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9936
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      26.31

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.226
_exptl_absorpt_coefficient_mu    0.290
_shelx_estimated_absorpt_T_min   0.919
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9629
_exptl_absorpt_correction_T_max  0.9969
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            58128
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.953
_diffrn_reflns_theta_max         27.126
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4964
_reflns_number_gt                4116
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 740)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0321P)²+1.5291P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4964
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0899
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 1.17665(4) 0.78043(3) 0.69558(3) 0.02604(11) Uani 1 1 d . . . . .
S1 S 0.79217(4) 0.60330(2) 0.28882(3) 0.01454(10) Uani 1 1 d . . . . .
O1 O 0.90657(12) 0.54888(7) 0.33792(9) 0.0206(3) Uani 1 1 d . . . . .
O2 O 0.73358(13) 0.59582(8) 0.18741(8) 0.0226(3) Uani 1 1 d . . . . .
N1 N 0.41916(14) 0.54643(9) 0.30738(9) 0.0169(3) Uani 1 1 d . . . . .
C1 C 0.53096(16) 0.54510(10) 0.28229(11) 0.0158(3) Uani 1 1 d . . . . .
C2 C 0.65577(16) 0.58700(10) 0.33780(11) 0.0142(3) Uani 1 1 d . . . . .
C3 C 0.66642(16) 0.62053(10) 0.42645(11) 0.0146(3) Uani 1 1 d . . . . .
C4 C 0.54564(17) 0.64950(11) 0.54487(11) 0.0192(3) Uani 1 1 d . . . . .
H4 H 0.627656 0.671242 0.589463 0.023 Uiso 1 1 calc R U . . .
C5 C 0.42660(18) 0.64854(12) 0.56697(12) 0.0228(4) Uani 1 1 d . . . . .
H5 H 0.426446 0.670366 0.626571 0.027 Uiso 1 1 calc R U . . .
C6 C 0.30413(18) 0.61557(12) 0.50238(13) 0.0233(4) Uani 1 1 d . . . . .
H6 H 0.222178 0.615303 0.518660 0.028 Uiso 1 1 calc R U . . .
C7 C 0.30291(17) 0.58388(11) 0.41609(12) 0.0207(4) Uani 1 1 d . . . . .
H7 H 0.220040 0.561897 0.372711 0.025 Uiso 1 1 calc R U . . .
C8 C 0.42416(17) 0.58380(10) 0.39157(11) 0.0164(3) Uani 1 1 d . . . . .
C9 C 0.54728(16) 0.61813(10) 0.45556(11) 0.0150(3) Uani 1 1 d . . . . .
C10 C 0.51581(17) 0.49211(10) 0.19585(11) 0.0166(3) Uani 1 1 d . . . . .
C11 C 0.60563(18) 0.42454(11) 0.19852(12) 0.0202(4) Uani 1 1 d . . . . .
H11 H 0.682124 0.414923 0.254075 0.024 Uiso 1 1 calc R U . . .
C12 C 0.58381(19) 0.37095(11) 0.12009(13) 0.0242(4) Uani 1 1 d . . . . .
H12 H 0.644323 0.324129 0.122601 0.029 Uiso 1 1 calc R U . . .
C13 C 0.47415(19) 0.38579(11) 0.03850(13) 0.0241(4) Uani 1 1 d . . . . .
H13 H 0.461233 0.350413 -0.015794 0.029 Uiso 1 1 calc R U . . .
C14 C 0.38298(18) 0.45226(12) 0.03584(12) 0.0231(4) Uani 1 1 d . . . . .
H14 H 0.307025 0.461905 -0.020038 0.028 Uiso 1 1 calc R U . . .
C15 C 0.40240(17) 0.50470(11) 0.11452(12) 0.0196(3) Uani 1 1 d . . . . .
H15 H 0.338440 0.549235 0.113067 0.024 Uiso 1 1 calc R U . . .
C16 C 0.84304(16) 0.71174(10) 0.31243(11) 0.0138(3) Uani 1 1 d . . . . .
C17 C 0.74739(17) 0.77673(11) 0.27692(11) 0.0168(3) Uani 1 1 d . . . . .
H17 H 0.654005 0.762953 0.244122 0.020 Uiso 1 1 calc R U . . .
C18 C 0.78952(18) 0.86175(11) 0.28980(12) 0.0204(4) Uani 1 1 d . . . . .
H18 H 0.724418 0.906466 0.265862 0.024 Uiso 1 1 calc R U . . .
C19 C 0.92648(19) 0.88256(11) 0.33754(12) 0.0207(4) Uani 1 1 d . . . . .
C20 C 1.02049(18) 0.81613(11) 0.37189(12) 0.0213(4) Uani 1 1 d . . . . .
H20 H 1.114077 0.829645 0.404369 0.026 Uiso 1 1 calc R U . . .
C21 C 0.97984(17) 0.73060(11) 0.35949(12) 0.0179(3) Uani 1 1 d . . . . .
H21 H 1.044761 0.685692 0.382891 0.021 Uiso 1 1 calc R U . . .
C22 C 0.9713(2) 0.97565(12) 0.35183(15) 0.0328(5) Uani 1 1 d . . . . .
H22A H 1.026132 0.989502 0.310838 0.049 Uiso 1 1 calc R U . . .
H22B H 1.026752 0.984906 0.418395 0.049 Uiso 1 1 calc R U . . .
H22C H 0.890075 1.012929 0.335520 0.049 Uiso 1 1 calc R U . . .
C23 C 0.79447(16) 0.65950(10) 0.49273(10) 0.0136(3) Uani 1 1 d . . . . .
C24 C 0.80105(17) 0.74804(10) 0.50974(11) 0.0168(3) Uani 1 1 d . . . . .
H24 H 0.724422 0.783169 0.477642 0.020 Uiso 1 1 calc R U . . .
C25 C 0.91716(17) 0.78561(10) 0.57253(11) 0.0179(3) Uani 1 1 d . . . . .
H25 H 0.921250 0.846031 0.583140 0.021 Uiso 1 1 calc R U . . .
C26 C 1.02733(17) 0.73326(11) 0.61959(11) 0.0173(3) Uani 1 1 d . . . . .
C27 C 1.02155(17) 0.64489(11) 0.60680(11) 0.0178(3) Uani 1 1 d . . . . .
H27 H 1.096506 0.609694 0.641663 0.021 Uiso 1 1 calc R U . . .
C28 C 0.90552(16) 0.60816(10) 0.54273(11) 0.0154(3) Uani 1 1 d . . . . .
H28 H 0.901647 0.547634 0.532821 0.018 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 C26 1.7455(16) . ?
S1 O2 1.4364(12) . ?
S1 O1 1.4403(12) . ?
S1 C16 1.7641(16) . ?
S1 C2 1.7972(16) . ?
N1 C1 1.320(2) . ?
N1 C8 1.367(2) . ?
C1 C2 1.437(2) . ?
C1 C10 1.492(2) . ?
C2 C3 1.389(2) . ?
C3 C9 1.427(2) . ?
C3 C23 1.493(2) . ?
C4 C5 1.368(2) . ?
C4 C9 1.421(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.410(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.372(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.409(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.418(2) . ?
C10 C11 1.390(2) . ?
C10 C15 1.395(2) . ?
C11 C12 1.391(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.384(2) . ?
C16 C17 1.389(2) . ?
C17 C18 1.383(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.394(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.393(3) . ?
C19 C22 1.511(2) . ?
C20 C21 1.386(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C28 1.394(2) . ?
C23 C24 1.396(2) . ?
C24 C25 1.384(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.386(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.384(2) . ?
C27 C28 1.386(2) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 118.72(7) . . ?
O2 S1 C16 106.41(7) . . ?
O1 S1 C16 108.55(7) . . ?
O2 S1 C2 107.36(7) . . ?
O1 S1 C2 109.19(7) . . ?
C16 S1 C2 105.89(7) . . ?
C1 N1 C8 119.30(14) . . ?
N1 C1 C2 121.90(14) . . ?
N1 C1 C10 113.33(14) . . ?
C2 C1 C10 124.66(14) . . ?
C3 C2 C1 119.71(14) . . ?
C3 C2 S1 120.10(12) . . ?
C1 C2 S1 120.02(12) . . ?
C2 C3 C9 117.91(14) . . ?
C2 C3 C23 124.03(14) . . ?
C9 C3 C23 118.07(13) . . ?
C5 C4 C9 120.34(16) . . ?
C5 C4 H4 119.8 . . ?
C9 C4 H4 119.8 . . ?
C4 C5 C6 120.79(16) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 120.21(16) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.22(16) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
N1 C8 C7 117.72(15) . . ?
N1 C8 C9 122.31(15) . . ?
C7 C8 C9 119.91(15) . . ?
C8 C9 C4 118.51(15) . . ?
C8 C9 C3 118.29(14) . . ?
C4 C9 C3 123.19(15) . . ?
C11 C10 C15 119.43(15) . . ?
C11 C10 C1 120.62(15) . . ?
C15 C10 C1 119.63(15) . . ?
C10 C11 C12 120.19(16) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.05(17) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.04(16) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.17(16) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C10 120.06(16) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
C21 C16 C17 121.14(15) . . ?
C21 C16 S1 119.32(12) . . ?
C17 C16 S1 119.34(12) . . ?
C18 C17 C16 119.30(15) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 120.74(16) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C20 C19 C18 118.80(15) . . ?
C20 C19 C22 120.86(17) . . ?
C18 C19 C22 120.33(17) . . ?
C21 C20 C19 121.13(16) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C16 C21 C20 118.89(15) . . ?
C16 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C28 C23 C24 118.92(14) . . ?
C28 C23 C3 121.02(14) . . ?
C24 C23 C3 119.95(14) . . ?
C25 C24 C23 121.20(15) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C24 C25 C26 118.62(15) . . ?
C24 C25 H25 120.7 . . ?
C26 C25 H25 120.7 . . ?
C27 C26 C25 121.37(15) . . ?
C27 C26 Cl1 119.64(13) . . ?
C25 C26 Cl1 118.99(13) . . ?
C26 C27 C28 119.44(15) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
C27 C28 C23 120.38(15) . . ?
C27 C28 H28 119.8 . . ?
C23 C28 H28 119.8 . . ?

_refine_diff_density_max         0.369
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_i17677
_database_code_depnum_ccdc_archive 'CCDC 1942499'
loop_
_audit_author_name
_audit_author_address
'Chieh-Kai Chan' 'Academia Sinica'
_audit_update_record             
;
2019-07-23 deposited with the CCDC.	2019-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H23 N O2 S'
_chemical_formula_sum            'C29 H23 N O2 S'
_chemical_formula_weight         449.54

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   10.1684(6)
_cell_length_b                   15.8049(10)
_cell_length_c                   15.0030(12)
_cell_angle_alpha                90
_cell_angle_beta                 109.404(2)
_cell_angle_gamma                90
_cell_volume                     2274.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9925
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      27.1

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.397
_exptl_crystal_size_mid          0.362
_exptl_crystal_size_min          0.296
_exptl_absorpt_coefficient_mu    0.170
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9576
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54947
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.932
_diffrn_reflns_theta_max         27.111
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5003
_reflns_number_gt                4308
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 740)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0362P)²+1.7726P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5003
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0937
_refine_ls_wR_factor_gt          0.0869
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.20759(4) 0.39707(2) 0.71211(2) 0.01439(9) Uani 1 1 d . . . . .
O1 O 0.09087(11) 0.45030(6) 0.66318(8) 0.0205(2) Uani 1 1 d . . . . .
O2 O 0.26716(12) 0.40402(7) 0.81308(7) 0.0222(2) Uani 1 1 d . . . . .
N1 N 0.58473(12) 0.45690(8) 0.69566(8) 0.0165(3) Uani 1 1 d . . . . .
C1 C 0.47172(15) 0.45649(9) 0.72027(10) 0.0153(3) Uani 1 1 d . . . . .
C2 C 0.34586(14) 0.41426(9) 0.66444(10) 0.0141(3) Uani 1 1 d . . . . .
C3 C 0.33578(15) 0.38157(9) 0.57656(10) 0.0142(3) Uani 1 1 d . . . . .
C4 C 0.45774(16) 0.35645(10) 0.45887(10) 0.0192(3) Uani 1 1 d . . . . .
H4 H 0.375259 0.333574 0.414834 0.023 Uiso 1 1 calc R U . . .
C5 C 0.57733(16) 0.36084(10) 0.43623(11) 0.0223(3) Uani 1 1 d . . . . .
H5 H 0.577252 0.340881 0.376482 0.027 Uiso 1 1 calc R U . . .
C6 C 0.70080(16) 0.39474(10) 0.50077(11) 0.0222(3) Uani 1 1 d . . . . .
H6 H 0.783182 0.397102 0.484242 0.027 Uiso 1 1 calc R U . . .
C7 C 0.70272(15) 0.42423(10) 0.58693(11) 0.0203(3) Uani 1 1 d . . . . .
H7 H 0.786317 0.446759 0.630060 0.024 Uiso 1 1 calc R U . . .
C8 C 0.58013(15) 0.42117(9) 0.61186(10) 0.0158(3) Uani 1 1 d . . . . .
C9 C 0.45660(15) 0.38599(9) 0.54802(10) 0.0152(3) Uani 1 1 d . . . . .
C10 C 0.48615(15) 0.50790(9) 0.80659(10) 0.0164(3) Uani 1 1 d . . . . .
C11 C 0.60330(16) 0.49728(10) 0.88699(10) 0.0191(3) Uani 1 1 d . . . . .
H11 H 0.670128 0.455026 0.887797 0.023 Uiso 1 1 calc R U . . .
C12 C 0.62271(16) 0.54804(10) 0.96568(11) 0.0222(3) Uani 1 1 d . . . . .
H12 H 0.701286 0.539464 1.020857 0.027 Uiso 1 1 calc R U . . .
C13 C 0.52740(17) 0.61136(10) 0.96387(11) 0.0238(3) Uani 1 1 d . . . . .
H13 H 0.540303 0.645874 1.017955 0.029 Uiso 1 1 calc R U . . .
C14 C 0.41336(17) 0.62427(10) 0.88313(11) 0.0233(3) Uani 1 1 d . . . . .
H14 H 0.349776 0.668840 0.881171 0.028 Uiso 1 1 calc R U . . .
C15 C 0.39192(16) 0.57210(10) 0.80506(11) 0.0197(3) Uani 1 1 d . . . . .
H15 H 0.312482 0.580319 0.750348 0.024 Uiso 1 1 calc R U . . .
C16 C 0.15689(15) 0.29044(9) 0.68812(10) 0.0141(3) Uani 1 1 d . . . . .
C17 C 0.25306(15) 0.22672(9) 0.72767(10) 0.0177(3) Uani 1 1 d . . . . .
H17 H 0.346612 0.240453 0.763684 0.021 Uiso 1 1 calc R U . . .
C18 C 0.21068(16) 0.14298(10) 0.71387(11) 0.0205(3) Uani 1 1 d . . . . .
H18 H 0.276123 0.099178 0.739996 0.025 Uiso 1 1 calc R U . . .
C19 C 0.07312(17) 0.12224(10) 0.66209(11) 0.0211(3) Uani 1 1 d . . . . .
C20 C -0.02086(16) 0.18723(10) 0.62387(11) 0.0206(3) Uani 1 1 d . . . . .
H20 H -0.114777 0.173725 0.588484 0.025 Uiso 1 1 calc R U . . .
C21 C 0.01982(15) 0.27146(9) 0.63637(10) 0.0176(3) Uani 1 1 d . . . . .
H21 H -0.045299 0.315331 0.609868 0.021 Uiso 1 1 calc R U . . .
C22 C 0.0279(2) 0.03094(11) 0.64802(13) 0.0325(4) Uani 1 1 d . . . . .
H22A H -0.024637 0.021030 0.581135 0.049 Uiso 1 1 calc R U . . .
H22B H -0.031415 0.018179 0.686146 0.049 Uiso 1 1 calc R U . . .
H22C H 0.110242 -0.005738 0.667617 0.049 Uiso 1 1 calc R U . . .
C23 C 0.20754(14) 0.34150(9) 0.51027(9) 0.0141(3) Uani 1 1 d . . . . .
C24 C 0.20514(15) 0.25457(9) 0.49371(10) 0.0175(3) Uani 1 1 d . . . . .
H24 H 0.284074 0.221126 0.526369 0.021 Uiso 1 1 calc R U . . .
C25 C 0.08911(16) 0.21653(9) 0.43026(10) 0.0187(3) Uani 1 1 d . . . . .
H25 H 0.088854 0.157097 0.420763 0.022 Uiso 1 1 calc R U . . .
C26 C -0.02731(15) 0.26400(10) 0.38010(10) 0.0179(3) Uani 1 1 d . . . . .
C27 C -0.02217(15) 0.35136(9) 0.39455(10) 0.0175(3) Uani 1 1 d . . . . .
H27 H -0.099189 0.385137 0.359350 0.021 Uiso 1 1 calc R U . . .
C28 C 0.09292(15) 0.39008(9) 0.45920(10) 0.0158(3) Uani 1 1 d . . . . .
H28 H 0.093455 0.449543 0.468562 0.019 Uiso 1 1 calc R U . . .
C29 C -0.15563(17) 0.22187(11) 0.31361(12) 0.0264(4) Uani 1 1 d . . . . .
H29A H -0.207983 0.262703 0.265813 0.040 Uiso 1 1 calc R U . . .
H29B H -0.214452 0.201626 0.349333 0.040 Uiso 1 1 calc R U . . .
H29C H -0.127819 0.173908 0.282479 0.040 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 O2 1.4367(11) . ?
S1 O1 1.4410(11) . ?
S1 C16 1.7641(14) . ?
S1 C2 1.7972(14) . ?
N1 C1 1.3186(19) . ?
N1 C8 1.3648(18) . ?
C1 C2 1.440(2) . ?
C1 C10 1.494(2) . ?
C2 C3 1.3877(19) . ?
C3 C9 1.431(2) . ?
C3 C23 1.4929(19) . ?
C4 C5 1.369(2) . ?
C4 C9 1.420(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.412(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.368(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.416(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.416(2) . ?
C10 C15 1.390(2) . ?
C10 C11 1.395(2) . ?
C11 C12 1.386(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.384(2) . ?
C16 C17 1.392(2) . ?
C17 C18 1.386(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.395(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(2) . ?
C19 C22 1.508(2) . ?
C20 C21 1.388(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C28 1.394(2) . ?
C23 C24 1.395(2) . ?
C24 C25 1.383(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.392(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.396(2) . ?
C26 C29 1.509(2) . ?
C27 C28 1.389(2) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?

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 118.68(7) . . ?
O2 S1 C16 106.28(7) . . ?
O1 S1 C16 108.56(7) . . ?
O2 S1 C2 107.25(7) . . ?
O1 S1 C2 109.26(6) . . ?
C16 S1 C2 106.11(7) . . ?
C1 N1 C8 119.31(12) . . ?
N1 C1 C2 121.89(13) . . ?
N1 C1 C10 113.35(12) . . ?
C2 C1 C10 124.66(13) . . ?
C3 C2 C1 119.74(13) . . ?
C3 C2 S1 120.08(11) . . ?
C1 C2 S1 120.02(10) . . ?
C2 C3 C9 117.80(13) . . ?
C2 C3 C23 124.29(13) . . ?
C9 C3 C23 117.91(12) . . ?
C5 C4 C9 120.20(14) . . ?
C5 C4 H4 119.9 . . ?
C9 C4 H4 119.9 . . ?
C4 C5 C6 120.66(14) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 120.50(14) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.02(14) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
N1 C8 C9 122.47(13) . . ?
N1 C8 C7 117.73(13) . . ?
C9 C8 C7 119.72(13) . . ?
C8 C9 C4 118.89(13) . . ?
C8 C9 C3 118.28(13) . . ?
C4 C9 C3 122.84(13) . . ?
C15 C10 C11 119.19(14) . . ?
C15 C10 C1 120.91(13) . . ?
C11 C10 C1 119.58(13) . . ?
C12 C11 C10 120.38(15) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.00(15) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 119.98(14) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.07(15) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 120.32(14) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C21 C16 C17 121.07(13) . . ?
C21 C16 S1 119.54(11) . . ?
C17 C16 S1 119.21(11) . . ?
C18 C17 C16 119.19(14) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 C18 C19 120.81(14) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C20 C19 C18 118.74(14) . . ?
C20 C19 C22 120.88(15) . . ?
C18 C19 C22 120.38(15) . . ?
C21 C20 C19 121.31(14) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C16 C21 C20 118.88(14) . . ?
C16 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C28 C23 C24 118.87(13) . . ?
C28 C23 C3 121.23(12) . . ?
C24 C23 C3 119.75(13) . . ?
C25 C24 C23 120.74(14) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C26 121.02(14) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C25 C26 C27 117.89(14) . . ?
C25 C26 C29 120.85(14) . . ?
C27 C26 C29 121.25(14) . . ?
C28 C27 C26 121.57(14) . . ?
C28 C27 H27 119.2 . . ?
C26 C27 H27 119.2 . . ?
C27 C28 C23 119.85(13) . . ?
C27 C28 H28 120.1 . . ?
C23 C28 H28 120.1 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

_refine_diff_density_max         0.415
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.049

