# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_936
_database_code_depnum_ccdc_archive 'CCDC 1998433'
loop_
_audit_author_name
_audit_author_address
'Long-Wu Ye'
;Xiamen University
China
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2020-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 N O3 S'
_chemical_formula_weight         377.44

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'
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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.15686(13)
_cell_length_b                   13.9511(2)
_cell_length_c                   14.2096(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.1253(14)
_cell_angle_gamma                90
_cell_volume                     1781.13(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8750
_cell_measurement_theta_min      4.4450
_cell_measurement_theta_max      75.3450

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.807
_shelx_estimated_absorpt_T_min   0.840
_shelx_estimated_absorpt_T_max   0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85052
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11842
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.483
_diffrn_reflns_theta_max         67.052
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3171
_reflns_number_gt                3015
_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-2013 (Sheldrick, 2013)'
_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)+(0.0315P)²+1.7059P]
 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         3171
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0822
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_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 0.50535(5) 0.78577(3) 0.25132(3) 0.01723(13) Uani 1 1 d . . . . .
O1 O 0.80898(13) 0.79491(9) 0.44774(9) 0.0207(3) Uani 1 1 d . . . . .
H1 H 0.7701 0.8324 0.4058 0.031 Uiso 1 1 calc R U . . .
O2 O 0.57391(14) 0.86043(9) 0.31308(9) 0.0236(3) Uani 1 1 d . . . . .
O3 O 0.51561(14) 0.78723(9) 0.15244(9) 0.0229(3) Uani 1 1 d . . . . .
N1 N 0.57979(16) 0.68260(10) 0.29584(10) 0.0168(3) Uani 1 1 d . . . . .
C1 C 0.3167(2) 0.77762(14) 0.25969(14) 0.0236(4) Uani 1 1 d . . . . .
H1A H 0.2658 0.8350 0.2346 0.035 Uiso 1 1 calc R U . . .
H1B H 0.3088 0.7700 0.3257 0.035 Uiso 1 1 calc R U . . .
H1C H 0.2724 0.7234 0.2234 0.035 Uiso 1 1 calc R U . . .
C2 C 0.55203(18) 0.59503(12) 0.24486(12) 0.0157(3) Uani 1 1 d . . . . .
C3 C 0.48493(19) 0.57745(13) 0.14967(12) 0.0187(4) Uani 1 1 d . . . . .
H3 H 0.4546 0.6273 0.1069 0.022 Uiso 1 1 calc R U . . .
C4 C 0.46552(19) 0.48226(13) 0.12180(12) 0.0204(4) Uani 1 1 d . . . . .
H4 H 0.4193 0.4681 0.0592 0.024 Uiso 1 1 calc R U . . .
C5 C 0.51358(19) 0.40706(13) 0.18535(12) 0.0194(4) Uani 1 1 d . . . . .
H5 H 0.4980 0.3440 0.1646 0.023 Uiso 1 1 calc R U . . .
C6 C 0.58389(19) 0.42550(12) 0.27855(12) 0.0179(4) Uani 1 1 d . . . . .
H6 H 0.6183 0.3755 0.3202 0.021 Uiso 1 1 calc R U . . .
C7 C 0.60245(18) 0.52098(12) 0.30918(12) 0.0152(3) Uani 1 1 d . . . . .
C8 C 0.66100(18) 0.56313(12) 0.40147(12) 0.0154(3) Uani 1 1 d . . . . .
C9 C 0.73284(18) 0.50861(12) 0.48718(12) 0.0155(3) Uani 1 1 d . . . . .
C10 C 0.69522(19) 0.52164(12) 0.57716(12) 0.0179(4) Uani 1 1 d . . . . .
H10 H 0.6203 0.5646 0.5839 0.021 Uiso 1 1 calc R U . . .
C11 C 0.7685(2) 0.47109(13) 0.65642(12) 0.0197(4) Uani 1 1 d . . . . .
H11 H 0.7433 0.4809 0.7160 0.024 Uiso 1 1 calc R U . . .
C12 C 0.8794(2) 0.40591(13) 0.64698(13) 0.0208(4) Uani 1 1 d . . . . .
H12 H 0.9300 0.3731 0.7004 0.025 Uiso 1 1 calc R U . . .
C13 C 0.91454(19) 0.38989(12) 0.55751(13) 0.0201(4) Uani 1 1 d . . . . .
H13 H 0.9867 0.3449 0.5506 0.024 Uiso 1 1 calc R U . . .
C14 C 0.84228(18) 0.44085(12) 0.47844(12) 0.0173(4) Uani 1 1 d . . . . .
H14 H 0.8667 0.4299 0.4188 0.021 Uiso 1 1 calc R U . . .
C15 C 0.64394(18) 0.66012(12) 0.39370(12) 0.0153(3) Uani 1 1 d . . . . .
C16 C 0.69861(19) 0.73268(12) 0.47157(12) 0.0173(4) Uani 1 1 d . . . . .
H16 H 0.7508 0.6947 0.5258 0.021 Uiso 1 1 calc R U . . .
C17 C 0.57667(19) 0.78580(12) 0.51067(12) 0.0158(3) Uani 1 1 d . . . . .
C18 C 0.60506(19) 0.87699(12) 0.54981(12) 0.0194(4) Uani 1 1 d . . . . .
H18 H 0.6950 0.9070 0.5473 0.023 Uiso 1 1 calc R U . . .
C19 C 0.5008(2) 0.92370(13) 0.59247(13) 0.0218(4) Uani 1 1 d . . . . .
H19 H 0.5219 0.9843 0.6189 0.026 Uiso 1 1 calc R U . . .
C20 C 0.3659(2) 0.88081(13) 0.59587(13) 0.0220(4) Uani 1 1 d . . . . .
H20 H 0.2963 0.9122 0.6246 0.026 Uiso 1 1 calc R U . . .
C21 C 0.3353(2) 0.79070(13) 0.55612(13) 0.0217(4) Uani 1 1 d . . . . .
H21 H 0.2443 0.7617 0.5576 0.026 Uiso 1 1 calc R U . . .
C22 C 0.44001(19) 0.74314(13) 0.51389(12) 0.0184(4) Uani 1 1 d . . . . .
H22 H 0.4186 0.6825 0.4877 0.022 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 1.4263(13) . ?
S1 O2 1.4271(13) . ?
S1 N1 1.6644(14) . ?
S1 C1 1.7580(18) . ?
O1 C16 1.422(2) . ?
N1 C2 1.418(2) . ?
N1 C15 1.436(2) . ?
C2 C3 1.395(2) . ?
C2 C7 1.397(2) . ?
C3 C4 1.387(3) . ?
C4 C5 1.399(3) . ?
C5 C6 1.380(2) . ?
C6 C7 1.402(2) . ?
C7 C8 1.443(2) . ?
C8 C15 1.364(2) . ?
C8 C9 1.478(2) . ?
C9 C10 1.399(2) . ?
C9 C14 1.400(2) . ?
C10 C11 1.387(2) . ?
C11 C12 1.389(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.385(3) . ?
C15 C16 1.512(2) . ?
C16 C17 1.531(2) . ?
C17 C18 1.393(2) . ?
C17 C22 1.394(2) . ?
C18 C19 1.388(3) . ?
C19 C20 1.382(3) . ?
C20 C21 1.384(3) . ?
C21 C22 1.394(2) . ?

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 119.38(8) . . ?
O3 S1 N1 106.66(7) . . ?
O2 S1 N1 107.35(7) . . ?
O3 S1 C1 108.66(9) . . ?
O2 S1 C1 109.10(9) . . ?
N1 S1 C1 104.72(8) . . ?
C2 N1 C15 107.82(13) . . ?
C2 N1 S1 122.08(12) . . ?
C15 N1 S1 128.16(12) . . ?
C3 C2 C7 122.15(16) . . ?
C3 C2 N1 130.45(16) . . ?
C7 C2 N1 107.38(14) . . ?
C4 C3 C2 116.95(16) . . ?
C3 C4 C5 121.78(16) . . ?
C6 C5 C4 120.67(16) . . ?
C5 C6 C7 118.76(16) . . ?
C2 C7 C6 119.64(15) . . ?
C2 C7 C8 108.13(15) . . ?
C6 C7 C8 132.15(16) . . ?
C15 C8 C7 108.30(15) . . ?
C15 C8 C9 127.07(15) . . ?
C7 C8 C9 124.57(15) . . ?
C10 C9 C14 118.39(16) . . ?
C10 C9 C8 122.49(15) . . ?
C14 C9 C8 119.11(15) . . ?
C11 C10 C9 120.67(16) . . ?
C10 C11 C12 120.18(16) . . ?
C13 C12 C11 119.78(16) . . ?
C14 C13 C12 120.10(16) . . ?
C13 C14 C9 120.83(16) . . ?
C8 C15 N1 108.31(14) . . ?
C8 C15 C16 126.04(15) . . ?
N1 C15 C16 125.33(15) . . ?
O1 C16 C15 112.63(14) . . ?
O1 C16 C17 113.12(14) . . ?
C15 C16 C17 115.34(14) . . ?
C18 C17 C22 118.45(16) . . ?
C18 C17 C16 119.60(15) . . ?
C22 C17 C16 121.83(15) . . ?
C19 C18 C17 120.80(17) . . ?
C20 C19 C18 120.45(17) . . ?
C19 C20 C21 119.39(16) . . ?
C20 C21 C22 120.40(17) . . ?
C21 C22 C17 120.49(16) . . ?

_refine_diff_density_max         0.326
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.055

_shelxl_version_number           2013-2


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and ethyl acetate'
