# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_c:\Users\zhoumi\Desktop\struct\ZM20161217_a
_database_code_depnum_ccdc_archive 'CCDC 1523303'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-07-25 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 H28 N2 O3 S'
_chemical_formula_weight         388.51

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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'

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

_cell_length_a                   8.62560(10)
_cell_length_b                   22.3286(3)
_cell_length_c                   10.6389(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2049.03(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9873
_cell_measurement_theta_min      4.5850
_cell_measurement_theta_max      73.1270

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.588
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86851
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadbas
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            14970
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.960
_diffrn_reflns_theta_max         73.377
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4061
_reflns_number_gt                3988
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    1.000

_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)+(0.0381P)²+0.3939P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1664 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(4)
_chemical_absolute_configuration s''s
_refine_ls_number_reflns         4061
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0231
_refine_ls_wR_factor_ref         0.0624
_refine_ls_wR_factor_gt          0.0619
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.21014(5) 0.63324(2) 0.71521(4) 0.01710(10) Uani 1 1 d . . . . .
O3 O 0.04074(14) 0.64200(5) 0.74159(11) 0.0228(3) Uani 1 1 d . . . . .
O2 O 0.55861(14) 0.58158(6) 0.50926(12) 0.0232(3) Uani 1 1 d . . . . .
N1 N 0.46612(16) 0.66487(6) 0.40697(13) 0.0174(3) Uani 1 1 d . . . . .
O1 O 0.84396(19) 0.55296(6) 0.62703(17) 0.0376(4) Uani 1 1 d . . . . .
H31 H 0.897(3) 0.5805(13) 0.657(2) 0.045 Uiso 1 1 d . U . . .
H32 H 0.767(3) 0.5692(13) 0.601(3) 0.045 Uiso 1 1 d . U . . .
N2 N 0.23527(17) 0.58035(6) 0.61006(13) 0.0182(3) Uani 1 1 d . . . . .
H2 H 0.2239 0.5424 0.6307 0.022 Uiso 1 1 calc R U . . .
C15 C 0.4518(2) 0.61234(7) 0.47070(15) 0.0175(3) Uani 1 1 d . . . . .
C8 C 0.32021(19) 0.69118(7) 0.38468(15) 0.0167(3) Uani 1 1 d . . . . .
C18 C 0.2885(2) 0.59586(7) 0.85653(16) 0.0216(3) Uani 1 1 d . . . . .
C10 C 0.1333(2) 0.76278(7) 0.32183(16) 0.0209(4) Uani 1 1 d . . . . .
H10 H 0.1072 0.8000 0.2841 0.025 Uiso 1 1 calc R U . . .
C7 C 0.6157(2) 0.69091(8) 0.37215(16) 0.0195(3) Uani 1 1 d . . . . .
H7A H 0.6945 0.6783 0.4344 0.023 Uiso 1 1 calc R U . . .
H7B H 0.6076 0.7351 0.3761 0.023 Uiso 1 1 calc R U . . .
C11 C 0.0160(2) 0.72670(8) 0.36767(16) 0.0209(4) Uani 1 1 d . . . . .
H11 H -0.0887 0.7395 0.3614 0.025 Uiso 1 1 calc R U . . .
C5 C 0.67012(19) 0.67307(8) 0.24205(17) 0.0208(4) Uani 1 1 d . . . . .
C9 C 0.2891(2) 0.74603(7) 0.32950(15) 0.0191(3) Uani 1 1 d . . . . .
H9 H 0.3696 0.7710 0.2984 0.023 Uiso 1 1 calc R U . . .
C12 C 0.0500(2) 0.67146(8) 0.42314(16) 0.0191(3) Uani 1 1 d . . . . .
H12 H -0.0304 0.6464 0.4541 0.023 Uiso 1 1 calc R U . . .
C14 C 0.2768(2) 0.59719(7) 0.48171(15) 0.0168(3) Uani 1 1 d . . . . .
C13 C 0.2036(2) 0.65422(7) 0.43175(14) 0.0168(3) Uani 1 1 d . . . . .
C16 C 0.2437(2) 0.54246(7) 0.39713(16) 0.0231(4) Uani 1 1 d . . . . .
H16A H 0.3043 0.5079 0.4286 0.028 Uiso 1 1 calc R U . . .
H16B H 0.1325 0.5320 0.4041 0.028 Uiso 1 1 calc R U . . .
C20 C 0.1907(2) 0.54096(8) 0.88832(18) 0.0277(4) Uani 1 1 d . . . . .
H20A H 0.2022 0.5109 0.8218 0.042 Uiso 1 1 calc R U . . .
H20B H 0.0815 0.5527 0.8952 0.042 Uiso 1 1 calc R U . . .
H20C H 0.2256 0.5240 0.9684 0.042 Uiso 1 1 calc R U . . .
C4 C 0.6464(2) 0.71068(9) 0.13963(17) 0.0254(4) Uani 1 1 d . . . . .
H4 H 0.5886 0.7466 0.1498 0.030 Uiso 1 1 calc R U . . .
C2 C 0.7068(3) 0.69602(9) 0.02215(18) 0.0321(4) Uani 1 1 d . . . . .
H2A H 0.6907 0.7221 -0.0472 0.038 Uiso 1 1 calc R U . . .
C6 C 0.7523(2) 0.61983(8) 0.22488(19) 0.0261(4) Uani 1 1 d . . . . .
H6 H 0.7670 0.5933 0.2936 0.031 Uiso 1 1 calc R U . . .
C21 C 0.4573(2) 0.58029(9) 0.83003(19) 0.0289(4) Uani 1 1 d . . . . .
H21A H 0.5028 0.5611 0.9042 0.043 Uiso 1 1 calc R U . . .
H21B H 0.5149 0.6170 0.8104 0.043 Uiso 1 1 calc R U . . .
H21C H 0.4628 0.5528 0.7584 0.043 Uiso 1 1 calc R U . . .
C3 C 0.8125(2) 0.60556(9) 0.1072(2) 0.0312(4) Uani 1 1 d . . . . .
H3 H 0.8693 0.5695 0.0963 0.037 Uiso 1 1 calc R U . . .
C1 C 0.7903(3) 0.64359(9) 0.00619(19) 0.0336(5) Uani 1 1 d . . . . .
H1 H 0.8321 0.6338 -0.0738 0.040 Uiso 1 1 calc R U . . .
C17 C 0.2831(3) 0.55248(8) 0.25885(17) 0.0329(4) Uani 1 1 d . . . . .
H17A H 0.2189 0.5850 0.2253 0.049 Uiso 1 1 calc R U . . .
H17B H 0.2629 0.5157 0.2115 0.049 Uiso 1 1 calc R U . . .
H17C H 0.3928 0.5632 0.2510 0.049 Uiso 1 1 calc R U . . .
C19 C 0.2773(3) 0.64344(8) 0.95957(17) 0.0304(4) Uani 1 1 d . . . . .
H19A H 0.1680 0.6514 0.9783 0.046 Uiso 1 1 calc R U . . .
H19B H 0.3273 0.6804 0.9308 0.046 Uiso 1 1 calc R U . . .
H19C H 0.3294 0.6290 1.0356 0.046 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 1.5007(13) . ?
S1 N2 1.6409(14) . ?
S1 C18 1.8477(17) . ?
O2 C15 1.220(2) . ?
N1 C15 1.361(2) . ?
N1 C8 1.409(2) . ?
N1 C7 1.463(2) . ?
O1 H31 0.83(3) . ?
O1 H32 0.81(3) . ?
N2 C14 1.461(2) . ?
N2 H2 0.8800 . ?
C15 C14 1.551(2) . ?
C8 C9 1.384(2) . ?
C8 C13 1.394(2) . ?
C18 C21 1.523(3) . ?
C18 C20 1.526(2) . ?
C18 C19 1.530(2) . ?
C10 C11 1.382(3) . ?
C10 C9 1.398(2) . ?
C10 H10 0.9500 . ?
C7 C5 1.515(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C11 C12 1.399(2) . ?
C11 H11 0.9500 . ?
C5 C4 1.391(3) . ?
C5 C6 1.396(3) . ?
C9 H9 0.9500 . ?
C12 C13 1.382(2) . ?
C12 H12 0.9500 . ?
C14 C13 1.517(2) . ?
C14 C16 1.544(2) . ?
C16 C17 1.526(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C4 C2 1.393(3) . ?
C4 H4 0.9500 . ?
C2 C1 1.385(3) . ?
C2 H2A 0.9500 . ?
C6 C3 1.392(3) . ?
C6 H6 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C3 C1 1.383(3) . ?
C3 H3 0.9500 . ?
C1 H1 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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 N2 110.48(7) . . ?
O3 S1 C18 105.24(8) . . ?
N2 S1 C18 100.45(7) . . ?
C15 N1 C8 111.22(13) . . ?
C15 N1 C7 123.31(14) . . ?
C8 N1 C7 125.42(14) . . ?
H31 O1 H32 105(3) . . ?
C14 N2 S1 118.97(11) . . ?
C14 N2 H2 120.5 . . ?
S1 N2 H2 120.5 . . ?
O2 C15 N1 125.73(16) . . ?
O2 C15 C14 125.93(15) . . ?
N1 C15 C14 108.31(13) . . ?
C9 C8 C13 122.42(16) . . ?
C9 C8 N1 127.83(15) . . ?
C13 C8 N1 109.71(14) . . ?
C21 C18 C20 112.72(15) . . ?
C21 C18 C19 110.60(16) . . ?
C20 C18 C19 111.34(15) . . ?
C21 C18 S1 107.59(12) . . ?
C20 C18 S1 109.93(13) . . ?
C19 C18 S1 104.26(11) . . ?
C11 C10 C9 121.83(15) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
N1 C7 C5 113.58(14) . . ?
N1 C7 H7A 108.8 . . ?
C5 C7 H7A 108.8 . . ?
N1 C7 H7B 108.8 . . ?
C5 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C10 C11 C12 120.60(16) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C4 C5 C6 119.11(17) . . ?
C4 C5 C7 120.75(16) . . ?
C6 C5 C7 120.06(16) . . ?
C8 C9 C10 116.61(15) . . ?
C8 C9 H9 121.7 . . ?
C10 C9 H9 121.7 . . ?
C13 C12 C11 118.35(16) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
N2 C14 C13 116.18(14) . . ?
N2 C14 C16 107.19(13) . . ?
C13 C14 C16 112.52(13) . . ?
N2 C14 C15 111.43(13) . . ?
C13 C14 C15 101.28(13) . . ?
C16 C14 C15 107.97(13) . . ?
C12 C13 C8 120.18(15) . . ?
C12 C13 C14 130.97(15) . . ?
C8 C13 C14 108.80(15) . . ?
C17 C16 C14 113.85(14) . . ?
C17 C16 H16A 108.8 . . ?
C14 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C14 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C5 C4 C2 120.38(18) . . ?
C5 C4 H4 119.8 . . ?
C2 C4 H4 119.8 . . ?
C1 C2 C4 120.21(19) . . ?
C1 C2 H2A 119.9 . . ?
C4 C2 H2A 119.9 . . ?
C3 C6 C5 120.14(19) . . ?
C3 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 C3 C6 120.42(18) . . ?
C1 C3 H3 119.8 . . ?
C6 C3 H3 119.8 . . ?
C3 C1 C2 119.72(17) . . ?
C3 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.033

