# 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_mjr18054_0m
_database_code_depnum_ccdc_archive 'CCDC 1842217'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2018-05-09 deposited with the CCDC.	2019-12-09 downloaded from the CCDC.
;
_audit_creation_date             2018-05-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H21 N O3 S'
_chemical_formula_sum            'C25 H21 N O3 S'
_chemical_formula_weight         415.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2924 0.4247 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.23890(10)
_cell_length_b                   9.9067(2)
_cell_length_c                   12.3018(2)
_cell_angle_alpha                70.3440(10)
_cell_angle_beta                 77.1870(10)
_cell_angle_gamma                80.7730(10)
_cell_volume                     1029.42(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8166
_cell_measurement_temperature    274(2)
_cell_measurement_theta_max      54.856
_cell_measurement_theta_min      4.142
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.921
_exptl_absorpt_coefficient_mu    1.047
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0669 before and 0.0440 after correction. The Ratio of minimum to maximum transmission is 0.8571. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10821
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.868
_diffrn_reflns_theta_min         4.141
_diffrn_ambient_temperature      274.11
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3519
_reflns_number_total             3823
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3823
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0521P)²+0.3316P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1076
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16), C17(H17),
 C20(H20), C21(H21), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.22473(4) 0.20405(4) 0.08925(3) 0.03726(14) Uani 1 1 d . . . . .
O1 O 0.03698(13) 0.09438(17) 0.31917(11) 0.0616(4) Uani 1 1 d . . . . .
O2 O 0.09923(14) 0.14544(13) 0.08011(11) 0.0521(3) Uani 1 1 d . . . . .
O3 O 0.35649(14) 0.20828(13) 0.00296(10) 0.0504(3) Uani 1 1 d . . . . .
N1 N 0.27859(13) 0.10598(13) 0.21960(10) 0.0343(3) Uani 1 1 d . . . . .
C1 C 0.16937(17) 0.07398(17) 0.32192(14) 0.0404(4) Uani 1 1 d . . . . .
C2 C 0.22904(18) 0.02943(18) 0.43365(13) 0.0423(4) Uani 1 1 d . . . . .
H2A H 0.319535 -0.035090 0.429980 0.051 Uiso 1 1 calc R . . . .
H2B H 0.156048 -0.017236 0.500329 0.051 Uiso 1 1 calc R . . . .
C3 C 0.25987(18) 0.17097(18) 0.44066(13) 0.0421(4) Uani 1 1 d . . . . .
C4 C 0.1432(2) 0.2426(2) 0.51459(17) 0.0602(5) Uani 1 1 d . . . . .
H4A H 0.098011 0.169812 0.583442 0.072 Uiso 1 1 calc R . . . .
H4B H 0.065725 0.294286 0.470171 0.072 Uiso 1 1 calc R . . . .
C5 C 0.2077(3) 0.3458(3) 0.55256(19) 0.0722(6) Uani 1 1 d . . . . .
H5A H 0.263651 0.291610 0.614186 0.087 Uiso 1 1 calc R . . . .
H5B H 0.127082 0.404959 0.584734 0.087 Uiso 1 1 calc R . . . .
C6 C 0.3088(2) 0.4419(2) 0.45278(17) 0.0585(5) Uani 1 1 d . . . . .
C7 C 0.3223(3) 0.5809(2) 0.4480(2) 0.0784(7) Uani 1 1 d . . . . .
H7 H 0.263720 0.617853 0.505267 0.094 Uiso 1 1 calc R . . . .
C8 C 0.4205(3) 0.6656(2) 0.3604(2) 0.0805(7) Uani 1 1 d . . . . .
H8 H 0.428534 0.758504 0.359251 0.097 Uiso 1 1 calc R . . . .
C9 C 0.5067(3) 0.6127(2) 0.27443(18) 0.0672(6) Uani 1 1 d . . . . .
H9 H 0.572830 0.669816 0.214744 0.081 Uiso 1 1 calc R . . . .
C10 C 0.4946(2) 0.47463(19) 0.27718(15) 0.0527(4) Uani 1 1 d . . . . .
H10 H 0.553105 0.439570 0.218743 0.063 Uiso 1 1 calc R . . . .
C11 C 0.3966(2) 0.38632(18) 0.36566(14) 0.0452(4) Uani 1 1 d . . . . .
C12 C 0.37712(17) 0.23954(17) 0.36920(13) 0.0390(3) Uani 1 1 d . . . . .
C13 C 0.48312(16) 0.16686(16) 0.29167(13) 0.0368(3) Uani 1 1 d . . . . .
C14 C 0.63699(18) 0.1559(2) 0.28781(15) 0.0480(4) Uani 1 1 d . . . . .
H14 H 0.673046 0.200125 0.330855 0.058 Uiso 1 1 calc R . . . .
C15 C 0.73661(19) 0.0814(2) 0.22212(17) 0.0551(5) Uani 1 1 d . . . . .
H15 H 0.838389 0.077629 0.220011 0.066 Uiso 1 1 calc R . . . .
C16 C 0.68559(19) 0.0123(2) 0.15943(17) 0.0519(4) Uani 1 1 d . . . . .
H16 H 0.752727 -0.038797 0.115692 0.062 Uiso 1 1 calc R . . . .
C17 C 0.53514(18) 0.01931(17) 0.16192(14) 0.0422(4) Uani 1 1 d . . . . .
H17 H 0.500545 -0.028700 0.120890 0.051 Uiso 1 1 calc R . . . .
C18 C 0.43443(16) 0.09765(15) 0.22530(12) 0.0337(3) Uani 1 1 d . . . . .
C19 C 0.17578(17) 0.37638(16) 0.10274(13) 0.0383(3) Uani 1 1 d . . . . .
C20 C 0.2855(2) 0.46971(19) 0.06693(18) 0.0544(5) Uani 1 1 d . . . . .
H20 H 0.381265 0.442479 0.033028 0.065 Uiso 1 1 calc R . . . .
C21 C 0.2516(2) 0.6042(2) 0.0820(2) 0.0634(5) Uani 1 1 d . . . . .
H21 H 0.325359 0.667269 0.057880 0.076 Uiso 1 1 calc R . . . .
C22 C 0.1101(2) 0.64655(19) 0.13224(17) 0.0559(5) Uani 1 1 d . . . . .
C23 C 0.0008(2) 0.5524(2) 0.16365(18) 0.0597(5) Uani 1 1 d . . . . .
H23 H -0.095839 0.580900 0.194934 0.072 Uiso 1 1 calc R . . . .
C24 C 0.03181(19) 0.4176(2) 0.14969(16) 0.0504(4) Uani 1 1 d . . . . .
H24 H -0.042673 0.355653 0.171430 0.061 Uiso 1 1 calc R . . . .
C25 C 0.0762(3) 0.7913(2) 0.1505(2) 0.0839(8) Uani 1 1 d . . . . .
H25A H -0.020751 0.796537 0.198293 0.126 Uiso 1 1 calc GR . . . .
H25B H 0.077802 0.865036 0.075963 0.126 Uiso 1 1 calc GR . . . .
H25C H 0.149701 0.805172 0.189073 0.126 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4184(12) . ?
S1 O3 1.4226(12) . ?
S1 N1 1.7069(13) . ?
S1 C19 1.7483(16) . ?
O1 C1 1.213(2) . ?
N1 C1 1.4049(19) . ?
N1 C18 1.4448(18) . ?
C1 C2 1.496(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.508(2) . ?
C3 C4 1.499(2) . ?
C3 C12 1.349(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.502(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.509(3) . ?
C6 C7 1.383(3) . ?
C6 C11 1.406(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.375(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.376(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.395(2) . ?
C11 C12 1.479(2) . ?
C12 C13 1.486(2) . ?
C13 C14 1.400(2) . ?
C13 C18 1.406(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.380(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.375(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(2) . ?
C19 C20 1.380(2) . ?
C19 C24 1.383(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.384(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.381(3) . ?
C22 C23 1.387(3) . ?
C22 C25 1.499(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.380(3) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 119.35(8) . . ?
O2 S1 N1 108.30(7) . . ?
O2 S1 C19 111.02(8) . . ?
O3 S1 N1 105.24(7) . . ?
O3 S1 C19 108.30(7) . . ?
N1 S1 C19 103.30(7) . . ?
C1 N1 S1 118.76(10) . . ?
C1 N1 C18 121.30(12) . . ?
C18 N1 S1 117.28(9) . . ?
O1 C1 N1 122.35(15) . . ?
O1 C1 C2 122.83(14) . . ?
N1 C1 C2 114.45(13) . . ?
C1 C2 H2A 111.2 . . ?
C1 C2 H2B 111.2 . . ?
C1 C2 C3 102.63(13) . . ?
H2A C2 H2B 109.2 . . ?
C3 C2 H2A 111.2 . . ?
C3 C2 H2B 111.2 . . ?
C4 C3 C2 117.48(14) . . ?
C12 C3 C2 120.42(14) . . ?
C12 C3 C4 121.36(16) . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C3 C4 C5 111.68(16) . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
C4 C5 C6 112.36(16) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C7 C6 C5 121.56(18) . . ?
C7 C6 C11 119.26(18) . . ?
C11 C6 C5 119.10(17) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.5(2) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.82(19) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.70(19) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.48(18) . . ?
C11 C10 H10 119.3 . . ?
C6 C11 C12 118.77(15) . . ?
C10 C11 C6 118.26(16) . . ?
C10 C11 C12 122.93(15) . . ?
C3 C12 C11 120.35(15) . . ?
C3 C12 C13 118.83(14) . . ?
C11 C12 C13 120.79(13) . . ?
C14 C13 C12 120.96(14) . . ?
C14 C13 C18 116.77(14) . . ?
C18 C13 C12 122.13(13) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 C13 121.92(16) . . ?
C15 C14 H14 119.0 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.10(16) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.73(16) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.44(16) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 N1 121.51(13) . . ?
C17 C18 N1 117.49(13) . . ?
C17 C18 C13 121.00(14) . . ?
C20 C19 S1 118.13(12) . . ?
C20 C19 C24 120.79(16) . . ?
C24 C19 S1 121.08(13) . . ?
C19 C20 H20 120.3 . . ?
C19 C20 C21 119.31(17) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 H21 119.4 . . ?
C22 C21 C20 121.17(18) . . ?
C22 C21 H21 119.4 . . ?
C21 C22 C23 118.21(17) . . ?
C21 C22 C25 120.5(2) . . ?
C23 C22 C25 121.3(2) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 C22 121.72(18) . . ?
C24 C23 H23 119.1 . . ?
C19 C24 H24 120.6 . . ?
C23 C24 C19 118.72(17) . . ?
C23 C24 H24 120.6 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
