# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_Compound-1
_database_code_depnum_ccdc_archive 'CCDC 1915354'
loop_
_audit_author_name
_audit_author_address
'Yu Du'
;Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2019-05-10 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H24 Cl N3 O4 S'
_chemical_formula_weight         534.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   9.5954(4)
_cell_length_b                   12.6894(4)
_cell_length_c                   11.2412(4)
_cell_angle_alpha                90
_cell_angle_beta                 112.927(4)
_cell_angle_gamma                90
_cell_volume                     1260.60(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(3)
_cell_measurement_reflns_used    3534
_cell_measurement_theta_min      4.2330
_cell_measurement_theta_max      73.3850

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             556
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    2.456
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.60035
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(3)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            9033
_diffrn_reflns_av_unetI/netI     0.0716
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.270
_diffrn_reflns_theta_max         73.351
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4900
_reflns_number_gt                4420
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.885
_reflns_Friedel_fraction_max     0.955
_reflns_Friedel_fraction_full    0.997

_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0285P)²] 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_abs_structure_details 
;
 Flack x determined using 1845 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(13)
_chemical_absolute_configuration .
_refine_ls_number_reflns         4900
_refine_ls_number_parameters     336
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.0936
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_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 0.80627(13) 0.20816(8) 0.78914(9) 0.0288(2) Uani 1 1 d . . . . .
S1 S 0.23319(11) 0.37415(8) 0.16648(9) 0.0192(2) Uani 1 1 d . . . . .
O1 O 0.2419(3) 0.4810(2) 0.6487(3) 0.0260(7) Uani 1 1 d . . . . .
O2 O 0.5677(3) 0.6322(2) 0.4267(2) 0.0189(6) Uani 1 1 d . . . . .
O3 O 0.1892(3) 0.4640(3) 0.0818(3) 0.0260(6) Uani 1 1 d . . . . .
O4 O 0.2206(4) 0.2699(2) 0.1129(3) 0.0264(7) Uani 1 1 d . . . . .
N1 N 0.2049(4) 0.6414(3) 0.8138(3) 0.0193(7) Uani 1 1 d . . . . .
N2 N 0.3628(4) 0.7420(3) 0.7621(3) 0.0204(7) Uani 1 1 d . . . . .
N3 N 0.4089(4) 0.3857(3) 0.2677(3) 0.0181(6) Uani 1 1 d . . . . .
H3 H 0.462578 0.330476 0.299249 0.022 Uiso 1 1 calc R U . . .
C1 C 0.0975(5) 0.5581(4) 0.8102(4) 0.0272(9) Uani 1 1 d . . . . .
H1A H 0.024391 0.550011 0.723428 0.041 Uiso 1 1 calc R U . . .
H1B H 0.046815 0.576842 0.865867 0.041 Uiso 1 1 calc R U . . .
H1C H 0.151050 0.493038 0.839011 0.041 Uiso 1 1 calc R U . . .
C2 C 0.2293(5) 0.7288(3) 0.8864(4) 0.0238(9) Uani 1 1 d . . . . .
H2 H 0.188141 0.744536 0.946732 0.029 Uiso 1 1 calc R U . . .
C3 C 0.3268(5) 0.7905(3) 0.8543(4) 0.0244(9) Uani 1 1 d . . . . .
H3A H 0.362994 0.855951 0.890356 0.029 Uiso 1 1 calc R U . . .
C4 C 0.2868(4) 0.6512(3) 0.7389(4) 0.0172(8) Uani 1 1 d . . . . .
C5 C 0.2921(4) 0.5695(3) 0.6479(4) 0.0176(8) Uani 1 1 d . . . . .
C6 C 0.3574(5) 0.6002(3) 0.5494(4) 0.0195(8) Uani 1 1 d . . . . .
H6A H 0.422628 0.661120 0.580321 0.023 Uiso 1 1 calc R U . . .
H6AB H 0.275862 0.619176 0.468631 0.023 Uiso 1 1 calc R U . . .
C7 C 0.4484(5) 0.5088(3) 0.5260(3) 0.0177(8) Uani 1 1 d . . . . .
H7 H 0.380356 0.447996 0.498382 0.021 Uiso 1 1 calc R U . . .
C8 C 0.5822(4) 0.4763(3) 0.6483(4) 0.0165(7) Uani 1 1 d . . . . .
C9 C 0.6557(5) 0.5465(3) 0.7476(4) 0.0200(8) Uani 1 1 d . . . . .
H9 H 0.624710 0.616541 0.739842 0.024 Uiso 1 1 calc R U . . .
C10 C 0.7752(5) 0.5136(3) 0.8586(4) 0.0222(9) Uani 1 1 d . . . . .
H10 H 0.822753 0.561502 0.924628 0.027 Uiso 1 1 calc R U . . .
C11 C 0.8241(5) 0.4093(3) 0.8717(4) 0.0203(8) Uani 1 1 d . . . . .
H11 H 0.904945 0.386982 0.945221 0.024 Uiso 1 1 calc R U . . .
C12 C 0.7496(5) 0.3398(3) 0.7727(4) 0.0194(8) Uani 1 1 d . . . . .
C13 C 0.6295(4) 0.3707(3) 0.6616(3) 0.0193(7) Uani 1 1 d . . . . .
H13 H 0.580863 0.322077 0.596660 0.023 Uiso 1 1 calc R U . . .
C14 C 0.4949(4) 0.5361(3) 0.4167(4) 0.0170(8) Uani 1 1 d . . . . .
C15 C 0.4726(4) 0.4884(3) 0.3035(4) 0.0171(7) Uani 1 1 d . . . . .
C16 C 0.5305(4) 0.5576(3) 0.2317(4) 0.0187(8) Uani 1 1 d . . . . .
C17 C 0.5359(5) 0.5579(3) 0.1086(4) 0.0216(8) Uani 1 1 d . . . . .
H17 H 0.494637 0.502764 0.051087 0.026 Uiso 1 1 calc R U . . .
C18 C 0.6042(5) 0.6422(4) 0.0752(4) 0.0243(9) Uani 1 1 d . . . . .
H18 H 0.609746 0.643057 -0.005567 0.029 Uiso 1 1 calc R U . . .
C19 C 0.6657(5) 0.7269(4) 0.1603(4) 0.0263(9) Uani 1 1 d . . . . .
H19 H 0.713320 0.781555 0.135667 0.032 Uiso 1 1 calc R U . . .
C20 C 0.6564(5) 0.7305(3) 0.2810(4) 0.0234(9) Uani 1 1 d . . . . .
H20 H 0.692426 0.787252 0.336912 0.028 Uiso 1 1 calc R U . . .
C21 C 0.5895(5) 0.6432(3) 0.3120(4) 0.0185(8) Uani 1 1 d . . . . .
C22 C 0.1263(4) 0.3784(4) 0.2631(3) 0.0198(7) Uani 1 1 d . . . . .
C23 C 0.0345(5) 0.4651(4) 0.2557(4) 0.0255(9) Uani 1 1 d . . . . .
H23 H 0.028939 0.520365 0.199777 0.031 Uiso 1 1 calc R U . . .
C24 C -0.0492(5) 0.4681(4) 0.3332(4) 0.0296(10) Uani 1 1 d . . . . .
H24 H -0.110533 0.525967 0.328813 0.035 Uiso 1 1 calc R U . . .
C25 C -0.0416(5) 0.3858(4) 0.4166(4) 0.0297(10) Uani 1 1 d . . . . .
C26 C 0.0480(5) 0.2987(4) 0.4199(4) 0.0277(10) Uani 1 1 d . . . . .
H26 H 0.051260 0.242514 0.474024 0.033 Uiso 1 1 calc R U . . .
C27 C 0.1328(5) 0.2941(3) 0.3439(4) 0.0234(9) Uani 1 1 d . . . . .
H27 H 0.192776 0.235713 0.347192 0.028 Uiso 1 1 calc R U . . .
C28 C -0.1316(6) 0.3882(5) 0.5005(5) 0.0434(14) Uani 1 1 d . . . . .
H28A H -0.168671 0.458327 0.501645 0.065 Uiso 1 1 calc R U . . .
H28B H -0.068007 0.367487 0.586798 0.065 Uiso 1 1 calc R U . . .
H28C H -0.215436 0.340428 0.466486 0.065 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 C12 1.744(4) . ?
S1 O3 1.439(3) . ?
S1 O4 1.440(3) . ?
S1 N3 1.632(3) . ?
S1 C22 1.762(4) . ?
O1 C5 1.224(5) . ?
O2 C14 1.388(5) . ?
O2 C21 1.391(4) . ?
N1 C2 1.343(5) . ?
N1 C4 1.363(5) . ?
N1 C1 1.465(5) . ?
N2 C4 1.334(5) . ?
N2 C3 1.361(5) . ?
N3 C15 1.430(5) . ?
C2 C3 1.371(6) . ?
C4 C5 1.472(5) . ?
C5 C6 1.520(5) . ?
C6 C7 1.534(5) . ?
C7 C14 1.503(5) . ?
C7 C8 1.527(5) . ?
C8 C9 1.388(6) . ?
C8 C13 1.405(6) . ?
C9 C10 1.390(6) . ?
C10 C11 1.393(6) . ?
C11 C12 1.381(6) . ?
C12 C13 1.386(6) . ?
C14 C15 1.348(6) . ?
C15 C16 1.442(6) . ?
C16 C21 1.385(6) . ?
C16 C17 1.405(6) . ?
C17 C18 1.381(6) . ?
C18 C19 1.407(6) . ?
C19 C20 1.394(6) . ?
C20 C21 1.390(6) . ?
C22 C27 1.389(6) . ?
C22 C23 1.391(6) . ?
C23 C24 1.396(6) . ?
C24 C25 1.387(7) . ?
C25 C26 1.391(7) . ?
C25 C28 1.507(6) . ?
C26 C27 1.393(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O4 119.76(18) . . ?
O3 S1 N3 110.32(18) . . ?
O4 S1 N3 105.64(18) . . ?
O3 S1 C22 107.0(2) . . ?
O4 S1 C22 108.2(2) . . ?
N3 S1 C22 104.98(17) . . ?
C14 O2 C21 105.4(3) . . ?
C2 N1 C4 107.1(3) . . ?
C2 N1 C1 124.5(3) . . ?
C4 N1 C1 128.1(3) . . ?
C4 N2 C3 104.9(3) . . ?
C15 N3 S1 119.4(3) . . ?
N1 C2 C3 106.7(3) . . ?
N2 C3 C2 110.1(4) . . ?
N2 C4 N1 111.2(3) . . ?
N2 C4 C5 125.4(3) . . ?
N1 C4 C5 123.4(4) . . ?
O1 C5 C4 121.4(3) . . ?
O1 C5 C6 121.1(4) . . ?
C4 C5 C6 117.5(3) . . ?
C5 C6 C7 110.8(3) . . ?
C14 C7 C8 112.7(3) . . ?
C14 C7 C6 109.6(3) . . ?
C8 C7 C6 112.6(3) . . ?
C9 C8 C13 119.0(4) . . ?
C9 C8 C7 122.5(4) . . ?
C13 C8 C7 118.5(3) . . ?
C8 C9 C10 120.8(4) . . ?
C9 C10 C11 120.5(4) . . ?
C12 C11 C10 118.3(4) . . ?
C11 C12 C13 122.3(4) . . ?
C11 C12 Cl1 118.9(3) . . ?
C13 C12 Cl1 118.8(3) . . ?
C12 C13 C8 119.1(4) . . ?
C15 C14 O2 111.2(3) . . ?
C15 C14 C7 132.8(4) . . ?
O2 C14 C7 115.9(3) . . ?
C14 C15 N3 124.6(4) . . ?
C14 C15 C16 107.5(4) . . ?
N3 C15 C16 127.8(3) . . ?
C21 C16 C17 118.5(4) . . ?
C21 C16 C15 105.2(3) . . ?
C17 C16 C15 136.3(4) . . ?
C18 C17 C16 118.3(4) . . ?
C17 C18 C19 121.7(4) . . ?
C20 C19 C18 121.2(4) . . ?
C21 C20 C19 115.4(4) . . ?
C16 C21 C20 125.0(3) . . ?
C16 C21 O2 110.7(3) . . ?
C20 C21 O2 124.3(4) . . ?
C27 C22 C23 121.0(4) . . ?
C27 C22 S1 119.4(3) . . ?
C23 C22 S1 119.6(3) . . ?
C22 C23 C24 119.3(4) . . ?
C25 C24 C23 120.6(4) . . ?
C24 C25 C26 119.0(4) . . ?
C24 C25 C28 121.1(5) . . ?
C26 C25 C28 119.9(5) . . ?
C25 C26 C27 121.3(4) . . ?
C22 C27 C26 118.7(4) . . ?

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.051



