# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_mo_zthso2a_0m
_database_code_depnum_ccdc_archive 'CCDC 1862564'
_audit_update_record             
;
2018-08-17 deposited with the CCDC.
2018-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H21 N O3 S'
_chemical_formula_weight         391.47

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'I a'
_space_group_name_Hall           'I -2ya'

_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, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   8.3257(7)
_cell_length_b                   15.1988(12)
_cell_length_c                   16.3404(13)
_cell_angle_alpha                90
_cell_angle_beta                 95.005(4)
_cell_angle_gamma                90
_cell_volume                     2059.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    303(2)
_cell_measurement_reflns_used    9824
_cell_measurement_theta_min      3.90
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.101
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.180
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      303(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            13021
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.895
_diffrn_reflns_theta_max         27.542
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             4422
_reflns_number_gt                4077
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_max     0.970
_reflns_Friedel_fraction_full    0.964

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1155P)²+0.1598P] 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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.17(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4422
_refine_ls_number_parameters     255
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1373
_refine_ls_wR_factor_gt          0.1310
_refine_ls_goodness_of_fit_ref   0.898
_refine_ls_restrained_S_all      0.898
_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
S1 S 1.23320(9) 0.25175(5) 0.52901(6) 0.0568(2) Uani 1 1 d . . . . .
O1 O 0.6824(4) 0.47750(17) 0.5567(2) 0.0856(9) Uani 1 1 d . . . . .
O2 O 1.3543(4) 0.2852(3) 0.47883(17) 0.0933(11) Uani 1 1 d . . . . .
O3 O 1.1923(4) 0.15987(18) 0.5269(2) 0.0914(11) Uani 1 1 d . . . . .
N2 N 0.7897(3) 0.36180(15) 0.49485(16) 0.0515(5) Uani 1 1 d . . . . .
C1 C 1.2952(3) 0.27913(19) 0.63219(18) 0.0503(6) Uani 1 1 d . . . . .
C2 C 1.3970(5) 0.3497(2) 0.6488(2) 0.0631(7) Uani 1 1 d . . . . .
H2 H 1.4336 0.3829 0.6064 0.076 Uiso 1 1 calc R U . . .
C3 C 1.4440(6) 0.3700(3) 0.7305(3) 0.0839(11) Uani 1 1 d . . . . .
H3 H 1.5142 0.4167 0.7430 0.101 Uiso 1 1 calc R U . . .
C4 C 1.3866(7) 0.3211(3) 0.7931(2) 0.0933(15) Uani 1 1 d . . . . .
H4 H 1.4168 0.3356 0.8475 0.112 Uiso 1 1 calc R U . . .
C5 C 1.2875(9) 0.2527(4) 0.7757(3) 0.0991(19) Uani 1 1 d . . . . .
H5 H 1.2505 0.2201 0.8184 0.119 Uiso 1 1 calc R U . . .
C6 C 1.2394(6) 0.2299(3) 0.6953(3) 0.0779(10) Uani 1 1 d . . . . .
H6 H 1.1709 0.1823 0.6837 0.093 Uiso 1 1 calc R U . . .
C7 C 1.0637(3) 0.31907(17) 0.50847(17) 0.0478(5) Uani 1 1 d . . . . .
H7 H 1.0835 0.3793 0.5090 0.057 Uiso 1 1 calc R U . . .
C8 C 0.9099(3) 0.29527(15) 0.49216(16) 0.0444(5) Uani 1 1 d . . . . .
C9 C 0.8481(3) 0.20648(16) 0.46740(19) 0.0518(6) Uani 1 1 d . . . . .
C10 C 0.7168(5) 0.1717(3) 0.5038(3) 0.0734(9) Uani 1 1 d . . . . .
H10 H 0.6640 0.2045 0.5414 0.088 Uiso 1 1 calc R U . . .
C11 C 0.6659(7) 0.0856(4) 0.4825(4) 0.1006(18) Uani 1 1 d . . . . .
H11 H 0.5812 0.0608 0.5079 0.121 Uiso 1 1 calc R U . . .
C12 C 0.7372(7) 0.0386(3) 0.4260(4) 0.1009(19) Uani 1 1 d . . . . .
H12 H 0.7032 -0.0186 0.4139 0.121 Uiso 1 1 calc R U . . .
C13 C 0.8592(6) 0.0746(2) 0.3866(3) 0.0840(13) Uani 1 1 d . . . . .
H13 H 0.9047 0.0427 0.3459 0.101 Uiso 1 1 calc R U . . .
C14 C 0.9164(4) 0.1591(2) 0.4070(2) 0.0636(8) Uani 1 1 d . . . . .
H14 H 0.9999 0.1832 0.3801 0.076 Uiso 1 1 calc R U . . .
C15 C 0.7776(4) 0.41647(18) 0.5612(2) 0.0587(7) Uani 1 1 d . . . . .
C16 C 0.8779(6) 0.3973(3) 0.6404(2) 0.0730(9) Uani 1 1 d . . . . .
H16A H 0.9834 0.4221 0.6383 0.109 Uiso 1 1 calc R U . . .
H16B H 0.8868 0.3348 0.6480 0.109 Uiso 1 1 calc R U . . .
H16C H 0.8273 0.4227 0.6855 0.109 Uiso 1 1 calc R U . . .
C17 C 0.6769(4) 0.3726(2) 0.4203(2) 0.0622(7) Uani 1 1 d . . . . .
H17A H 0.5949 0.4152 0.4315 0.075 Uiso 1 1 calc R U . . .
H17B H 0.6234 0.3169 0.4076 0.075 Uiso 1 1 calc R U . . .
C18 C 0.7589(3) 0.4025(2) 0.3470(2) 0.0569(7) Uani 1 1 d . . . . .
C19 C 0.7703(6) 0.3460(3) 0.2817(3) 0.0859(13) Uani 1 1 d . . . . .
H19 H 0.7295 0.2892 0.2840 0.103 Uiso 1 1 calc R U . . .
C20 C 0.8428(10) 0.3736(5) 0.2126(4) 0.114(2) Uani 1 1 d . . . . .
H20 H 0.8522 0.3348 0.1693 0.137 Uiso 1 1 calc R U . . .
C21 C 0.8988(8) 0.4555(6) 0.2082(4) 0.125(3) Uani 1 1 d . . . . .
H21 H 0.9440 0.4741 0.1610 0.150 Uiso 1 1 calc R U . . .
C22 C 0.8903(7) 0.5132(4) 0.2736(4) 0.1068(19) Uani 1 1 d . . . . .
H22 H 0.9314 0.5699 0.2707 0.128 Uiso 1 1 calc R U . . .
C23 C 0.8203(5) 0.4860(3) 0.3429(3) 0.0774(10) Uani 1 1 d . . . . .
H23 H 0.8148 0.5244 0.3869 0.093 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.437(3) . ?
S1 O2 1.446(3) . ?
S1 C7 1.752(3) . ?
S1 C1 1.769(3) . ?
O1 C15 1.219(4) . ?
N2 C15 1.377(4) . ?
N2 C8 1.426(3) . ?
N2 C17 1.481(4) . ?
C1 C2 1.379(5) . ?
C1 C6 1.386(5) . ?
C2 C3 1.393(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.341(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.335(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.488(3) . ?
C9 C14 1.384(5) . ?
C9 C10 1.393(5) . ?
C10 C11 1.409(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.344(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.400(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.506(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.500(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C23 1.373(5) . ?
C18 C19 1.379(6) . ?
C19 C20 1.392(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.333(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.390(11) . ?
C21 H21 0.9300 . ?
C22 C23 1.381(8) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O2 120.2(2) . . ?
O3 S1 C7 112.19(15) . . ?
O2 S1 C7 106.03(19) . . ?
O3 S1 C1 107.47(18) . . ?
O2 S1 C1 107.32(17) . . ?
C7 S1 C1 102.03(13) . . ?
C15 N2 C8 123.5(3) . . ?
C15 N2 C17 119.8(3) . . ?
C8 N2 C17 116.7(2) . . ?
C2 C1 C6 120.9(3) . . ?
C2 C1 S1 119.6(2) . . ?
C6 C1 S1 119.5(3) . . ?
C1 C2 C3 118.5(4) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.4(4) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 121.1(4) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 118.9(4) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
C8 C7 S1 128.5(2) . . ?
C8 C7 H7 115.7 . . ?
S1 C7 H7 115.7 . . ?
C7 C8 N2 117.7(2) . . ?
C7 C8 C9 127.1(2) . . ?
N2 C8 C9 115.1(2) . . ?
C14 C9 C10 119.5(3) . . ?
C14 C9 C8 120.8(3) . . ?
C10 C9 C8 119.6(3) . . ?
C9 C10 C11 118.5(5) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
C12 C11 C10 121.4(5) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 120.2(4) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C14 120.4(4) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C13 119.7(4) . . ?
C9 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
O1 C15 N2 120.2(3) . . ?
O1 C15 C16 120.6(3) . . ?
N2 C15 C16 119.1(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 C18 113.0(3) . . ?
N2 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
N2 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C23 C18 C19 119.1(4) . . ?
C23 C18 C17 121.1(4) . . ?
C19 C18 C17 119.8(3) . . ?
C18 C19 C20 120.3(5) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 120.3(6) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C20 120.4(5) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 119.7(5) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C18 C23 C22 120.2(5) . . ?
C18 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 S1 C1 C2 155.1(3) . . . . ?
O2 S1 C1 C2 24.5(3) . . . . ?
C7 S1 C1 C2 -86.8(3) . . . . ?
O3 S1 C1 C6 -25.5(3) . . . . ?
O2 S1 C1 C6 -156.2(3) . . . . ?
C7 S1 C1 C6 92.6(3) . . . . ?
C6 C1 C2 C3 0.5(6) . . . . ?
S1 C1 C2 C3 179.9(3) . . . . ?
C1 C2 C3 C4 -1.2(6) . . . . ?
C2 C3 C4 C5 1.1(8) . . . . ?
C3 C4 C5 C6 -0.5(9) . . . . ?
C4 C5 C6 C1 -0.1(8) . . . . ?
C2 C1 C6 C5 0.1(7) . . . . ?
S1 C1 C6 C5 -179.3(4) . . . . ?
O3 S1 C7 C8 0.1(3) . . . . ?
O2 S1 C7 C8 133.1(3) . . . . ?
C1 S1 C7 C8 -114.6(3) . . . . ?
S1 C7 C8 N2 166.8(2) . . . . ?
S1 C7 C8 C9 -16.2(4) . . . . ?
C15 N2 C8 C7 -53.2(4) . . . . ?
C17 N2 C8 C7 125.0(3) . . . . ?
C15 N2 C8 C9 129.5(3) . . . . ?
C17 N2 C8 C9 -52.4(3) . . . . ?
C7 C8 C9 C14 -46.4(4) . . . . ?
N2 C8 C9 C14 130.7(3) . . . . ?
C7 C8 C9 C10 135.4(3) . . . . ?
N2 C8 C9 C10 -47.5(4) . . . . ?
C14 C9 C10 C11 5.1(6) . . . . ?
C8 C9 C10 C11 -176.7(4) . . . . ?
C9 C10 C11 C12 -2.5(7) . . . . ?
C10 C11 C12 C13 -1.5(8) . . . . ?
C11 C12 C13 C14 2.9(7) . . . . ?
C10 C9 C14 C13 -3.8(5) . . . . ?
C8 C9 C14 C13 178.1(3) . . . . ?
C12 C13 C14 C9 -0.3(5) . . . . ?
C8 N2 C15 O1 172.8(3) . . . . ?
C17 N2 C15 O1 -5.3(5) . . . . ?
C8 N2 C15 C16 -10.0(4) . . . . ?
C17 N2 C15 C16 171.9(3) . . . . ?
C15 N2 C17 C18 113.8(3) . . . . ?
C8 N2 C17 C18 -64.4(4) . . . . ?
N2 C17 C18 C23 -69.9(4) . . . . ?
N2 C17 C18 C19 111.4(4) . . . . ?
C23 C18 C19 C20 -0.2(6) . . . . ?
C17 C18 C19 C20 178.5(5) . . . . ?
C18 C19 C20 C21 -1.3(9) . . . . ?
C19 C20 C21 C22 2.1(10) . . . . ?
C20 C21 C22 C23 -1.3(9) . . . . ?
C19 C18 C23 C22 1.0(6) . . . . ?
C17 C18 C23 C22 -177.7(4) . . . . ?
C21 C22 C23 C18 -0.3(7) . . . . ?

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.029

_shelxl_version_number           2014-3



