# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_171115a_a
_database_code_depnum_ccdc_archive 'CCDC 1586556'
_audit_update_record             
;
2017-11-20 deposited with the CCDC.
2018-01-09 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         ?
_chemical_formula_sum            'C22 H17 N O2 S'
_chemical_formula_weight         359.42

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'
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                   7.3596(8)
_cell_length_b                   10.4885(12)
_cell_length_c                   23.677(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.831(4)
_cell_angle_gamma                90
_cell_volume                     1814.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      27.52

_exptl_crystal_description       sheet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   0.6761
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.194
_shelx_estimated_absorpt_T_min   0.918
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23471
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.103
_diffrn_reflns_theta_max         27.100
_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             4014
_reflns_number_gt                3072
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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+0.9536P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0196(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4014
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1170
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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 0.38173(7) 0.67483(5) 0.69178(2) 0.04853(17) Uani 1 1 d . . . . .
O1 O 0.56733(18) 0.71857(16) 0.69516(7) 0.0620(4) Uani 1 1 d . . . . .
O2 O 0.3376(2) 0.58080(16) 0.73224(7) 0.0671(5) Uani 1 1 d . . . . .
N1 N 0.2579(3) 0.40727(17) 0.57516(10) 0.0632(5) Uani 1 1 d . . . . .
C1 C 0.2494(3) 0.47201(19) 0.52486(10) 0.0533(5) Uani 1 1 d . . . . .
C2 C 0.2163(3) 0.4017(2) 0.47406(13) 0.0687(7) Uani 1 1 d . . . . .
H2 H 0.199932 0.313860 0.475641 0.082 Uiso 1 1 calc R U . . .
C3 C 0.2080(3) 0.4603(3) 0.42306(13) 0.0725(8) Uani 1 1 d . . . . .
H3 H 0.188290 0.411490 0.390103 0.087 Uiso 1 1 calc R U . . .
C4 C 0.2285(3) 0.5934(3) 0.41831(10) 0.0634(6) Uani 1 1 d . . . . .
C5 C 0.2608(3) 0.6634(2) 0.46736(9) 0.0529(5) Uani 1 1 d . . . . .
H5 H 0.275453 0.751235 0.464838 0.063 Uiso 1 1 calc R U . . .
C6 C 0.2726(3) 0.60599(18) 0.52158(9) 0.0445(5) Uani 1 1 d . . . . .
C7 C 0.2152(5) 0.6557(3) 0.36077(11) 0.0949(10) Uani 1 1 d . . . . .
H7A H 0.251287 0.596000 0.333466 0.142 Uiso 1 1 calc R U . . .
H7B H 0.294513 0.728631 0.362522 0.142 Uiso 1 1 calc R U . . .
H7C H 0.091314 0.682279 0.349586 0.142 Uiso 1 1 calc R U . . .
C8 C 0.3116(2) 0.67528(17) 0.57318(8) 0.0402(4) Uani 1 1 d . . . . .
C9 C 0.3380(3) 0.81690(17) 0.57139(7) 0.0402(4) Uani 1 1 d . . . . .
C10 C 0.1880(3) 0.89651(19) 0.55977(8) 0.0518(5) Uani 1 1 d . . . . .
H10 H 0.071099 0.862105 0.552291 0.062 Uiso 1 1 calc R U . . .
C11 C 0.2124(4) 1.0275(2) 0.55933(10) 0.0633(6) Uani 1 1 d . . . . .
H11 H 0.111522 1.080949 0.551868 0.076 Uiso 1 1 calc R U . . .
C12 C 0.3848(4) 1.0790(2) 0.56986(10) 0.0658(7) Uani 1 1 d . . . . .
H12 H 0.400394 1.166944 0.569932 0.079 Uiso 1 1 calc R U . . .
C13 C 0.5335(4) 1.0004(2) 0.58023(10) 0.0612(6) Uani 1 1 d . . . . .
H13 H 0.650427 1.035095 0.586678 0.073 Uiso 1 1 calc R U . . .
C14 C 0.5104(3) 0.86965(19) 0.58114(9) 0.0492(5) Uani 1 1 d . . . . .
H14 H 0.612059 0.816847 0.588395 0.059 Uiso 1 1 calc R U . . .
C15 C 0.3215(3) 0.60723(18) 0.62327(9) 0.0448(5) Uani 1 1 d . . . . .
C16 C 0.2916(3) 0.4736(2) 0.62187(11) 0.0587(6) Uani 1 1 d . . . . .
H16 H 0.296295 0.430665 0.656368 0.070 Uiso 1 1 calc R U . . .
C17 C 0.2370(2) 0.80656(19) 0.69670(7) 0.0417(4) Uani 1 1 d . . . . .
C18 C 0.3109(3) 0.9267(2) 0.70362(8) 0.0501(5) Uani 1 1 d . . . . .
H18 H 0.436634 0.938823 0.705266 0.060 Uiso 1 1 calc R U . . .
C19 C 0.1960(3) 1.0289(2) 0.70808(10) 0.0602(6) Uani 1 1 d . . . . .
H19 H 0.244249 1.110659 0.712804 0.072 Uiso 1 1 calc R U . . .
C20 C 0.0104(3) 1.0104(2) 0.70558(10) 0.0625(6) Uani 1 1 d . . . . .
H20 H -0.066504 1.080076 0.707967 0.075 Uiso 1 1 calc R U . . .
C21 C -0.0626(3) 0.8895(2) 0.69956(10) 0.0600(6) Uani 1 1 d . . . . .
H21 H -0.188244 0.877734 0.698453 0.072 Uiso 1 1 calc R U . . .
C22 C 0.0498(3) 0.7864(2) 0.69520(9) 0.0508(5) Uani 1 1 d . . . . .
H22 H 0.001501 0.704517 0.691315 0.061 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 O1 1.4341(15) . ?
S1 O2 1.4387(15) . ?
S1 C17 1.757(2) . ?
S1 C15 1.777(2) . ?
N1 C16 1.305(3) . ?
N1 C1 1.366(3) . ?
C1 C2 1.407(3) . ?
C1 C6 1.419(3) . ?
C2 C3 1.350(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.410(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(3) . ?
C4 C7 1.504(4) . ?
C5 C6 1.411(3) . ?
C5 H5 0.9300 . ?
C6 C8 1.421(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C15 1.378(3) . ?
C8 C9 1.499(2) . ?
C9 C14 1.379(3) . ?
C9 C10 1.386(3) . ?
C10 C11 1.386(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.418(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(3) . ?
C17 C22 1.390(3) . ?
C18 C19 1.377(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.374(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.373(3) . ?
C21 H21 0.9300 . ?
C22 H22 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
O1 S1 O2 118.09(9) . . ?
O1 S1 C17 109.01(10) . . ?
O2 S1 C17 107.96(9) . . ?
O1 S1 C15 108.12(9) . . ?
O2 S1 C15 106.43(10) . . ?
C17 S1 C15 106.67(9) . . ?
C16 N1 C1 117.26(18) . . ?
N1 C1 C2 118.0(2) . . ?
N1 C1 C6 123.1(2) . . ?
C2 C1 C6 118.8(2) . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 121.9(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 118.2(2) . . ?
C5 C4 C7 121.4(2) . . ?
C3 C4 C7 120.4(2) . . ?
C4 C5 C6 121.8(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 118.54(19) . . ?
C5 C6 C8 123.23(18) . . ?
C1 C6 C8 118.21(19) . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C15 C8 C6 117.35(17) . . ?
C15 C8 C9 122.93(17) . . ?
C6 C8 C9 119.72(17) . . ?
C14 C9 C10 119.18(18) . . ?
C14 C9 C8 120.83(17) . . ?
C10 C9 C8 120.00(18) . . ?
C9 C10 C11 119.9(2) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 119.9(2) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 120.5(2) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C8 C15 C16 120.0(2) . . ?
C8 C15 S1 124.09(15) . . ?
C16 C15 S1 115.88(16) . . ?
N1 C16 C15 124.1(2) . . ?
N1 C16 H16 118.0 . . ?
C15 C16 H16 118.0 . . ?
C18 C17 C22 121.28(19) . . ?
C18 C17 S1 119.62(15) . . ?
C22 C17 S1 119.06(16) . . ?
C17 C18 C19 118.98(19) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C20 C19 C18 120.3(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.5(2) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 120.1(2) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C17 118.9(2) . . ?
C21 C22 H22 120.6 . . ?
C17 C22 H22 120.6 . . ?

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
C16 N1 C1 C2 178.9(2) . . . . ?
C16 N1 C1 C6 -0.9(3) . . . . ?
N1 C1 C2 C3 -179.4(2) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C2 C3 C4 C7 -178.9(2) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C7 C4 C5 C6 179.6(2) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C4 C5 C6 C8 177.95(19) . . . . ?
N1 C1 C6 C5 -179.91(19) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
N1 C1 C6 C8 1.8(3) . . . . ?
C2 C1 C6 C8 -178.05(18) . . . . ?
C5 C6 C8 C15 -179.17(18) . . . . ?
C1 C6 C8 C15 -1.0(3) . . . . ?
C5 C6 C8 C9 1.5(3) . . . . ?
C1 C6 C8 C9 179.67(17) . . . . ?
C15 C8 C9 C14 76.5(2) . . . . ?
C6 C8 C9 C14 -104.2(2) . . . . ?
C15 C8 C9 C10 -103.5(2) . . . . ?
C6 C8 C9 C10 75.7(2) . . . . ?
C14 C9 C10 C11 -1.4(3) . . . . ?
C8 C9 C10 C11 178.63(19) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C10 C11 C12 C13 0.7(4) . . . . ?
C11 C12 C13 C14 -1.2(4) . . . . ?
C10 C9 C14 C13 1.0(3) . . . . ?
C8 C9 C14 C13 -179.06(19) . . . . ?
C12 C13 C14 C9 0.3(3) . . . . ?
C6 C8 C15 C16 -0.5(3) . . . . ?
C9 C8 C15 C16 178.76(18) . . . . ?
C6 C8 C15 S1 176.21(14) . . . . ?
C9 C8 C15 S1 -4.5(3) . . . . ?
O1 S1 C15 C8 -64.46(18) . . . . ?
O2 S1 C15 C8 167.73(16) . . . . ?
C17 S1 C15 C8 52.65(18) . . . . ?
O1 S1 C15 C16 112.39(16) . . . . ?
O2 S1 C15 C16 -15.41(18) . . . . ?
C17 S1 C15 C16 -130.49(16) . . . . ?
C1 N1 C16 C15 -0.8(3) . . . . ?
C8 C15 C16 N1 1.5(3) . . . . ?
S1 C15 C16 N1 -175.48(18) . . . . ?
O1 S1 C17 C18 -1.00(18) . . . . ?
O2 S1 C17 C18 128.44(17) . . . . ?
C15 S1 C17 C18 -117.52(16) . . . . ?
O1 S1 C17 C22 -179.08(15) . . . . ?
O2 S1 C17 C22 -49.65(18) . . . . ?
C15 S1 C17 C22 64.39(17) . . . . ?
C22 C17 C18 C19 -1.2(3) . . . . ?
S1 C17 C18 C19 -179.25(16) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C18 C19 C20 C21 1.1(4) . . . . ?
C19 C20 C21 C22 -0.9(4) . . . . ?
C20 C21 C22 C17 -0.3(3) . . . . ?
C18 C17 C22 C21 1.4(3) . . . . ?
S1 C17 C22 C21 179.43(16) . . . . ?

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.044

