# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_exp_4416
_database_code_depnum_ccdc_archive 'CCDC 1844331'
_audit_update_record             
;
2018-05-21 deposited with the CCDC.
2018-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 N O4 S'
_chemical_formula_weight         383.45

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      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                   5.2634(5)
_cell_length_b                   12.909(2)
_cell_length_c                   14.964(2)
_cell_angle_alpha                73.896(14)
_cell_angle_beta                 89.385(10)
_cell_angle_gamma                80.113(11)
_cell_volume                     961.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1617
_cell_measurement_theta_min      3.6550
_cell_measurement_theta_max      25.4220

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.195
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6090
_diffrn_reflns_av_unetI/netI     0.0891
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.860
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_full        25.047
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3376
_reflns_number_gt                2129
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+3.2000P] 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         3376
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_gt           0.0786
_refine_ls_wR_factor_ref         0.1960
_refine_ls_wR_factor_gt          0.1430
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_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
S10 S 0.7594(3) 0.80340(12) 0.35469(10) 0.0482(4) Uani 1 1 d . . . . .
O15 O 0.4512(7) 0.9505(3) 0.4137(3) 0.0560(11) Uani 1 1 d . . . . .
O14 O 1.1404(7) 0.7496(3) 0.4871(3) 0.0585(11) Uani 1 1 d . . . . .
N12 N 0.8128(8) 0.8795(3) 0.5027(3) 0.0419(10) Uani 1 1 d . . . . .
H12 H 0.7596 0.9233 0.5357 0.050 Uiso 1 1 calc R U . . .
O17 O 0.7425(9) 0.8144(4) 0.0526(3) 0.0733(14) Uani 1 1 d . . . . .
O19 O 0.7336(11) 0.9505(4) 0.1176(3) 0.0873(17) Uani 1 1 d . . . . .
C20 C 1.1706(10) 0.8131(4) 0.6199(4) 0.0435(13) Uani 1 1 d . . . . .
C11 C 0.6546(10) 0.8877(4) 0.4273(4) 0.0423(12) Uani 1 1 d . . . . .
C13 C 1.0434(10) 0.8111(4) 0.5320(4) 0.0446(13) Uani 1 1 d . . . . .
C6 C 0.3513(11) 0.6040(5) 0.3448(4) 0.0530(15) Uani 1 1 d . . . . .
H6 H 0.4657 0.6355 0.3713 0.064 Uiso 1 1 calc R U . . .
C21 C 1.0747(11) 0.8851(5) 0.6710(4) 0.0548(15) Uani 1 1 d . . . . .
H21 H 0.9227 0.9350 0.6512 0.066 Uiso 1 1 calc R U . . .
C9 C 0.4773(10) 0.8483(5) 0.2747(4) 0.0464(13) Uani 1 1 d . . . . .
H9A H 0.3275 0.8244 0.3068 0.056 Uiso 1 1 calc R U . . .
H9B H 0.4427 0.9276 0.2524 0.056 Uiso 1 1 calc R U . . .
C7 C 0.4420(11) 0.7135(5) 0.1841(4) 0.0557(16) Uani 1 1 d . . . . .
H7 H 0.4758 0.6991 0.1272 0.067 Uiso 1 1 calc R U . . .
C8 C 0.5276(10) 0.7998(5) 0.1927(4) 0.0487(14) Uani 1 1 d . . . . .
C25 C 1.3934(11) 0.7385(5) 0.6520(5) 0.0611(17) Uani 1 1 d . . . . .
H25 H 1.4585 0.6899 0.6183 0.073 Uiso 1 1 calc R U . . .
C1 C 0.3026(10) 0.6347(5) 0.2470(4) 0.0472(13) Uani 1 1 d . . . . .
C16 C 0.6762(12) 0.8621(6) 0.1178(4) 0.0604(17) Uani 1 1 d . . . . .
C5 C 0.2221(12) 0.5251(5) 0.3996(5) 0.0638(18) Uani 1 1 d . . . . .
H5 H 0.2610 0.5002 0.4633 0.077 Uiso 1 1 calc R U . . .
C4 C 0.0402(12) 0.4829(5) 0.3632(5) 0.0640(18) Uani 1 1 d . . . . .
H4 H -0.0502 0.4336 0.4022 0.077 Uiso 1 1 calc R U . . .
C22 C 1.2047(12) 0.8825(5) 0.7510(4) 0.0606(16) Uani 1 1 d . . . . .
H22 H 1.1426 0.9321 0.7842 0.073 Uiso 1 1 calc R U . . .
C2 C 0.1218(12) 0.5911(5) 0.2120(5) 0.0640(17) Uani 1 1 d . . . . .
H2 H 0.0842 0.6138 0.1482 0.077 Uiso 1 1 calc R U . . .
C3 C -0.0088(12) 0.5138(5) 0.2684(5) 0.0680(19) Uani 1 1 d . . . . .
H3 H -0.1273 0.4835 0.2425 0.082 Uiso 1 1 calc R U . . .
C24 C 1.5204(13) 0.7346(6) 0.7323(5) 0.076(2) Uani 1 1 d . . . . .
H24 H 1.6698 0.6835 0.7534 0.091 Uiso 1 1 calc R U . . .
C23 C 1.4238(13) 0.8078(6) 0.7821(5) 0.0699(19) Uani 1 1 d . . . . .
H23 H 1.5087 0.8059 0.8369 0.084 Uiso 1 1 calc R U . . .
C18 C 0.8925(15) 0.8701(7) -0.0213(5) 0.094(3) Uani 1 1 d . . . . .
H18A H 0.9183 0.8307 -0.0674 0.140 Uiso 1 1 calc R U . . .
H18B H 1.0569 0.8734 0.0040 0.140 Uiso 1 1 calc R U . . .
H18C H 0.8019 0.9430 -0.0494 0.140 Uiso 1 1 calc R U . . .
C10 C 0.3650(17) 0.5302(7) 0.9802(6) 0.106(3) Uani 1 1 d . . . . .
H10A H 0.3652 0.5463 0.9129 0.127 Uiso 1 1 calc R U . . .
H10B H 0.3313 0.5995 0.9953 0.127 Uiso 1 1 calc R U . . .
C12 C 0.1405(17) 0.4672(7) 1.0156(6) 0.108(3) Uani 1 1 d . . . . .
H12A H 0.1530 0.4437 1.0831 0.129 Uiso 1 1 calc R U . . .
H12B H 0.1645 0.4018 0.9944 0.129 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
S10 C11 1.763(5) . ?
S10 C9 1.825(5) . ?
O15 C11 1.208(6) . ?
O14 C13 1.221(6) . ?
N12 C13 1.369(6) . ?
N12 C11 1.378(6) . ?
N12 H12 0.8600 . ?
O17 C16 1.306(8) . ?
O17 C18 1.448(7) . ?
O19 C16 1.229(7) . ?
C20 C25 1.379(8) . ?
C20 C21 1.388(8) . ?
C20 C13 1.491(8) . ?
C6 C5 1.391(8) . ?
C6 C1 1.420(8) . ?
C6 H6 0.9300 . ?
C21 C22 1.375(8) . ?
C21 H21 0.9300 . ?
C9 C8 1.527(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C7 C8 1.309(8) . ?
C7 C1 1.472(7) . ?
C7 H7 0.9300 . ?
C8 C16 1.486(7) . ?
C25 C24 1.366(9) . ?
C25 H25 0.9300 . ?
C1 C2 1.362(8) . ?
C5 C4 1.365(9) . ?
C5 H5 0.9300 . ?
C4 C3 1.377(9) . ?
C4 H4 0.9300 . ?
C22 C23 1.362(9) . ?
C22 H22 0.9300 . ?
C2 C3 1.391(8) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C24 C23 1.387(10) . ?
C24 H24 0.9300 . ?
C23 H23 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C10 C10 1.536(17) 2_667 ?
C10 C12 1.554(12) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 C12 1.577(17) 2_567 ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

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
C11 S10 C9 96.8(2) . . ?
C13 N12 C11 128.7(5) . . ?
C13 N12 H12 115.6 . . ?
C11 N12 H12 115.6 . . ?
C16 O17 C18 116.9(6) . . ?
C25 C20 C21 118.8(6) . . ?
C25 C20 C13 117.8(5) . . ?
C21 C20 C13 123.4(5) . . ?
O15 C11 N12 119.8(5) . . ?
O15 C11 S10 122.5(4) . . ?
N12 C11 S10 117.6(4) . . ?
O14 C13 N12 120.3(5) . . ?
O14 C13 C20 121.2(5) . . ?
N12 C13 C20 118.4(5) . . ?
C5 C6 C1 117.8(6) . . ?
C5 C6 H6 121.1 . . ?
C1 C6 H6 121.1 . . ?
C22 C21 C20 119.9(5) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C8 C9 S10 109.4(4) . . ?
C8 C9 H9A 109.8 . . ?
S10 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
S10 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
C8 C7 C1 132.5(6) . . ?
C8 C7 H7 113.7 . . ?
C1 C7 H7 113.7 . . ?
C7 C8 C16 120.7(6) . . ?
C7 C8 C9 124.8(5) . . ?
C16 C8 C9 114.4(5) . . ?
C24 C25 C20 121.4(7) . . ?
C24 C25 H25 119.3 . . ?
C20 C25 H25 119.3 . . ?
C2 C1 C6 118.8(5) . . ?
C2 C1 C7 120.2(6) . . ?
C6 C1 C7 120.9(5) . . ?
O19 C16 O17 122.8(6) . . ?
O19 C16 C8 123.0(6) . . ?
O17 C16 C8 114.3(6) . . ?
C4 C5 C6 122.3(6) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C5 C4 C3 119.7(6) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C23 C22 C21 120.6(6) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C1 C2 C3 122.3(6) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C2 118.9(6) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C25 C24 C23 119.2(6) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C22 C23 C24 120.2(6) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
O17 C18 H18A 109.5 . . ?
O17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C10 C12 115.3(9) 2_667 . ?
C10 C10 H10A 108.5 2_667 . ?
C12 C10 H10A 108.5 . . ?
C10 C10 H10B 108.5 2_667 . ?
C12 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C10 C12 C12 116.0(9) . 2_567 ?
C10 C12 H12A 108.3 . . ?
C12 C12 H12A 108.3 2_567 . ?
C10 C12 H12B 108.3 . . ?
C12 C12 H12B 108.3 2_567 . ?
H12A C12 H12B 107.4 . . ?

_refine_diff_density_max         0.608
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.102

