# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_20200529LI_ZNZ4932_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2019802'
loop_
_audit_author_name
_audit_author_address
'zheng jing'
;nanchang university
China
;
_audit_update_record             
;
2020-07-29 deposited with the CCDC.	2023-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 N O3 S'
_chemical_formula_weight         353.42

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'
Br Br -0.2901 2.4595 '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                   9.424(4)
_cell_length_b                   9.886(4)
_cell_length_c                   10.482(4)
_cell_angle_alpha                69.255(12)
_cell_angle_beta                 76.260(14)
_cell_angle_gamma                89.585(14)
_cell_volume                     884.0(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    4776
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      28.25

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.202
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.984
_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      193(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            8429
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.233
_diffrn_reflns_theta_max         28.311
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             4233
_reflns_number_gt                3610
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0778P)²+0.5926P] 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         4233
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1548
_refine_ls_wR_factor_gt          0.1469
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
C1 C 0.7581(2) 0.2153(2) 0.8101(2) 0.0355(4) Uani 1 1 d . . . . .
H1 H 0.712432 0.136841 0.798187 0.043 Uiso 1 1 calc R U . . .
C2 C 0.7798(3) 0.2000(3) 0.9404(2) 0.0443(5) Uani 1 1 d . . . . .
H2 H 0.746044 0.112190 1.018593 0.053 Uiso 1 1 calc R U . . .
C3 C 0.8511(3) 0.3133(3) 0.9571(2) 0.0463(6) Uani 1 1 d . . . . .
H3 H 0.865201 0.302735 1.046785 0.056 Uiso 1 1 calc R U . . .
C4 C 0.9018(3) 0.4418(3) 0.8429(2) 0.0410(5) Uani 1 1 d . . . . .
H4 H 0.953228 0.517551 0.853934 0.049 Uiso 1 1 calc R U . . .
C5 C 0.8771(2) 0.4591(2) 0.7129(2) 0.0341(4) Uani 1 1 d . . . . .
H5 H 0.910237 0.547489 0.635261 0.041 Uiso 1 1 calc R U . . .
C6 C 0.8035(2) 0.3466(2) 0.6957(2) 0.0291(4) Uani 1 1 d . . . . .
C7 C 0.7677(2) 0.3622(2) 0.5584(2) 0.0289(4) Uani 1 1 d . . . . .
C8 C 0.7367(2) 0.50356(19) 0.47559(19) 0.0290(4) Uani 1 1 d . . . . .
H8 H 0.752194 0.582952 0.503097 0.035 Uiso 1 1 calc R U . . .
C9 C 0.6854(2) 0.52866(18) 0.35789(19) 0.0261(3) Uani 1 1 d . . . . .
C10 C 0.7023(2) 0.79325(18) 0.28959(18) 0.0265(4) Uani 1 1 d . . . . .
C11 C 0.8517(2) 0.8321(2) 0.2618(2) 0.0321(4) Uani 1 1 d . . . . .
H11 H 0.922065 0.771568 0.234793 0.038 Uiso 1 1 calc R U . . .
C12 C 0.8974(2) 0.9599(2) 0.2736(2) 0.0358(4) Uani 1 1 d . . . . .
H12 H 0.999024 0.986408 0.255206 0.043 Uiso 1 1 calc R U . . .
C13 C 0.7939(3) 1.0486(2) 0.3125(2) 0.0345(4) Uani 1 1 d . . . . .
H13 H 0.824778 1.135627 0.321041 0.041 Uiso 1 1 calc R U . . .
C14 C 0.6457(3) 1.0098(2) 0.3388(2) 0.0369(4) Uani 1 1 d . . . . .
H14 H 0.575544 1.071166 0.364386 0.044 Uiso 1 1 calc R U . . .
C15 C 0.5982(2) 0.8813(2) 0.3280(2) 0.0324(4) Uani 1 1 d . . . . .
H15 H 0.496556 0.854815 0.346516 0.039 Uiso 1 1 calc R U . . .
C16 C 0.5548(3) 0.5165(2) 0.1740(2) 0.0388(5) Uani 1 1 d . . . . .
H16A H 0.573969 0.496839 0.085374 0.047 Uiso 1 1 calc R U . . .
H16B H 0.447574 0.505011 0.215303 0.047 Uiso 1 1 calc R U . . .
C17 C 0.6169(2) 0.6700(2) 0.1452(2) 0.0348(4) Uani 1 1 d . . . . .
H17 H 0.539224 0.738682 0.127660 0.042 Uiso 1 1 calc R U . . .
C18 C 0.7505(2) 0.7224(2) 0.0212(2) 0.0389(5) Uani 1 1 d . . . . .
H18A H 0.803764 0.805763 0.025897 0.047 Uiso 1 1 calc R U . . .
H18B H 0.817123 0.643721 0.027397 0.047 Uiso 1 1 calc R U . . .
C19 C 0.7098(3) 0.7679(3) -0.1184(2) 0.0435(5) Uani 1 1 d . . . . .
C20 C 0.8078(4) 0.8528(3) -0.3632(3) 0.0601(8) Uani 1 1 d . . . . .
H20A H 0.733807 0.789221 -0.371320 0.090 Uiso 1 1 calc R U . . .
H20B H 0.900500 0.857136 -0.431641 0.090 Uiso 1 1 calc R U . . .
H20C H 0.774498 0.950462 -0.382145 0.090 Uiso 1 1 calc R U . . .
N1 N 0.65489(18) 0.66153(16) 0.27605(17) 0.0278(3) Uani 1 1 d . . . . .
O1 O 0.76208(18) 0.25315(15) 0.52599(16) 0.0392(4) Uani 1 1 d . . . . .
O2 O 0.5874(3) 0.7763(3) -0.1337(2) 0.0789(7) Uani 1 1 d . . . . .
O3 O 0.8292(2) 0.7962(2) -0.22322(17) 0.0525(5) Uani 1 1 d . . . . .
S1 S 0.64689(6) 0.39228(5) 0.29744(5) 0.03358(16) Uani 1 1 d . . . . .


_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
C1 C2 1.384(3) . ?
C1 C6 1.403(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.393(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.401(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.510(3) . ?
C7 O1 1.245(2) . ?
C7 C8 1.431(2) . ?
C8 C9 1.372(2) . ?
C8 H8 0.9500 . ?
C9 N1 1.363(2) . ?
C9 S1 1.7528(18) . ?
C10 C15 1.389(3) . ?
C10 C11 1.396(3) . ?
C10 N1 1.444(2) . ?
C11 C12 1.393(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.401(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.530(3) . ?
C16 S1 1.825(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N1 1.472(2) . ?
C17 C18 1.516(3) . ?
C17 H17 1.0000 . ?
C18 C19 1.513(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O2 1.200(3) . ?
C19 O3 1.324(3) . ?
C20 O3 1.437(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C2 C1 C6 120.1(2) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 119.41(18) . . ?
C5 C6 C7 122.35(17) . . ?
C1 C6 C7 118.23(18) . . ?
O1 C7 C8 123.99(17) . . ?
O1 C7 C6 119.32(16) . . ?
C8 C7 C6 116.65(16) . . ?
C9 C8 C7 122.42(17) . . ?
C9 C8 H8 118.8 . . ?
C7 C8 H8 118.8 . . ?
N1 C9 C8 124.22(16) . . ?
N1 C9 S1 111.92(13) . . ?
C8 C9 S1 123.85(14) . . ?
C15 C10 C11 120.74(17) . . ?
C15 C10 N1 119.39(17) . . ?
C11 C10 N1 119.86(16) . . ?
C12 C11 C10 119.84(18) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 119.88(19) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 119.89(17) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.84(18) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C10 C15 C14 118.81(19) . . ?
C10 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C17 C16 S1 106.55(13) . . ?
C17 C16 H16A 110.4 . . ?
S1 C16 H16A 110.4 . . ?
C17 C16 H16B 110.4 . . ?
S1 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
N1 C17 C18 110.62(17) . . ?
N1 C17 C16 105.04(16) . . ?
C18 C17 C16 113.00(18) . . ?
N1 C17 H17 109.4 . . ?
C18 C17 H17 109.4 . . ?
C16 C17 H17 109.4 . . ?
C19 C18 C17 112.05(18) . . ?
C19 C18 H18A 109.2 . . ?
C17 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
C17 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
O2 C19 O3 124.1(2) . . ?
O2 C19 C18 125.6(2) . . ?
O3 C19 C18 110.3(2) . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C9 N1 C10 121.61(15) . . ?
C9 N1 C17 116.28(15) . . ?
C10 N1 C17 119.13(14) . . ?
C19 O3 C20 116.3(2) . . ?
C9 S1 C16 91.25(9) . . ?

_refine_diff_density_max         0.798
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_20200709LI_ZNZ5223_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2019886'
loop_
_audit_author_name
_audit_author_address
'zheng jing'
;nanchang university
China
;
_audit_update_record             
;
2020-07-29 deposited with the CCDC.	2023-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 N2 O3 S'
_chemical_formula_weight         380.45

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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   26.464(11)
_cell_length_b                   9.374(4)
_cell_length_c                   19.700(10)
_cell_angle_alpha                90
_cell_angle_beta                 130.263(13)
_cell_angle_gamma                90
_cell_volume                     3729(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    2183
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      27.49

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             1600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.198
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.984
_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      193(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            14077
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.395
_diffrn_reflns_theta_max         27.826
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             4284
_reflns_number_gt                3222
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0967P)²+12.3025P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4284
_refine_ls_number_parameters     318
_refine_ls_number_restraints     186
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0728
_refine_ls_wR_factor_ref         0.2074
_refine_ls_wR_factor_gt          0.1944
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.073
_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
C1 C 0.4353(3) 0.6993(7) 0.8144(5) 0.0441(18) Uani 0.483(5) 1 d D U P A 1
H1A H 0.410289 0.784725 0.788630 0.053 Uiso 0.483(5) 1 calc R U P A 1
C2 C 0.4999(4) 0.7077(9) 0.8856(5) 0.059(2) Uani 0.483(5) 1 d D U P A 1
H2A H 0.517395 0.798470 0.912500 0.071 Uiso 0.483(5) 1 calc R U P A 1
C3 C 0.5397(2) 0.6001(6) 0.9198(3) 0.0701(13) Uani 0.483(5) 1 d D U P A 1
H3A H 0.586445 0.611023 0.962922 0.084 Uiso 0.483(5) 1 calc R U P A 1
C4 C 0.5092(3) 0.4656(9) 0.8888(5) 0.060(2) Uani 0.483(5) 1 d D U P A 1
H4A H 0.534897 0.382330 0.918892 0.072 Uiso 0.483(5) 1 calc R U P A 1
C5 C 0.4433(3) 0.4516(8) 0.8164(5) 0.0477(19) Uani 0.483(5) 1 d D U P A 1
H5B H 0.423968 0.360571 0.792159 0.057 Uiso 0.483(5) 1 calc R U P A 1
C6 C 0.40575(15) 0.5764(4) 0.7795(2) 0.0360(7) Uani 0.483(5) 1 d D U P A 1
C7 C 0.29566(14) 0.5179(3) 0.70869(18) 0.0260(6) Uani 1 1 d . U . . .
C8 C 0.22166(13) 0.5146(3) 0.62834(17) 0.0228(5) Uani 1 1 d . U . . .
C9 C 0.18817(14) 0.5322(3) 0.66890(18) 0.0257(6) Uani 1 1 d . U . . .
H9A H 0.197666 0.631585 0.692759 0.031 Uiso 1 1 calc R U . . .
C10 C 0.22297(14) 0.4314(3) 0.74889(18) 0.0294(6) Uani 1 1 d . U . . .
H10A H 0.205869 0.332892 0.729304 0.035 Uiso 1 1 calc R U . . .
H10B H 0.216252 0.463285 0.790468 0.035 Uiso 1 1 calc R U . . .
C11 C 0.11393(14) 0.5153(4) 0.6041(2) 0.0338(7) Uani 1 1 d . U . . .
H11A H 0.095013 0.573654 0.550531 0.041 Uiso 1 1 calc R U . . .
H11B H 0.102689 0.414257 0.585291 0.041 Uiso 1 1 calc R U . . .
C12 C 0.08367(18) 0.5597(5) 0.6435(3) 0.0539(11) Uani 1 1 d . U . . .
O3 O 0.0270(4) 0.6546(9) 0.5734(5) 0.051(2) Uani 0.4 1 d . . P B 1
C13 C -0.0063(5) 0.7171(15) 0.6042(9) 0.076(4) Uani 0.4 1 d . U P B 1
H13A H -0.042745 0.772822 0.555926 0.114 Uiso 0.4 1 d R U P B 1
H13B H -0.022562 0.645200 0.620531 0.114 Uiso 0.4 1 d R U P B 1
H13C H 0.024172 0.777964 0.654287 0.114 Uiso 0.4 1 d R U P B 1
C15 C 0.20294(13) 0.6368(3) 0.56393(18) 0.0240(5) Uani 1 1 d . U . . .
C16 C 0.15985(18) 0.6610(4) 0.4091(2) 0.0428(8) Uani 1 1 d . U . . .
H16A H 0.145767 0.596512 0.360499 0.064 Uiso 1 1 calc R U . . .
H16B H 0.122839 0.723060 0.389794 0.064 Uiso 1 1 calc R U . . .
H16C H 0.196942 0.719568 0.425388 0.064 Uiso 1 1 calc R U . . .
C17 C 0.18011(14) 0.4279(3) 0.48895(18) 0.0268(6) Uani 1 1 d . U . . .
C18 C 0.16034(16) 0.3326(4) 0.4225(2) 0.0367(7) Uani 1 1 d . U . . .
H18A H 0.144085 0.364502 0.365712 0.044 Uiso 1 1 calc R U . . .
C19 C 0.16512(17) 0.1874(4) 0.4417(2) 0.0407(8) Uani 1 1 d . U . . .
H19A H 0.151933 0.119169 0.397285 0.049 Uiso 1 1 calc R U . . .
C20 C 0.18851(16) 0.1415(4) 0.5237(2) 0.0384(7) Uani 1 1 d . U . . .
H20A H 0.191300 0.042177 0.535298 0.046 Uiso 1 1 calc R U . . .
C21 C 0.20820(15) 0.2394(3) 0.5900(2) 0.0315(6) Uani 1 1 d . U . . .
H21A H 0.224688 0.207483 0.646812 0.038 Uiso 1 1 calc R U . . .
C1' C 0.4307(4) 0.6230(9) 0.8643(5) 0.0498(19) Uani 0.517(5) 1 d . U P A 2
H1'A H 0.401429 0.643876 0.875365 0.060 Uiso 0.517(5) 1 calc R U P A 2
C2' C 0.4993(4) 0.6380(10) 0.9318(5) 0.055(2) Uani 0.517(5) 1 d . U P A 2
H2'A H 0.516251 0.676913 0.987546 0.066 Uiso 0.517(5) 1 calc R U P A 2
C3' C 0.5397(2) 0.6001(6) 0.9198(3) 0.0701(13) Uani 0.517(5) 1 d . U P A 2
H3'A H 0.584888 0.582485 0.969645 0.084 Uiso 0.517(5) 1 calc R U P A 2
C4' C 0.5169(4) 0.5844(9) 0.8314(5) 0.0510(19) Uani 0.517(5) 1 d . U P A 2
H4'A H 0.546847 0.584776 0.820190 0.061 Uiso 0.517(5) 1 calc R U P A 2
C5' C 0.4494(3) 0.5687(8) 0.7631(5) 0.0421(16) Uani 0.517(5) 1 d . U P A 2
H5'A H 0.432674 0.552490 0.704146 0.051 Uiso 0.517(5) 1 calc R U P A 2
C6' C 0.40575(15) 0.5764(4) 0.7795(2) 0.0360(7) Uani 0.517(5) 1 d . U P A 2
O3' O 0.0244(3) 0.4987(10) 0.6012(4) 0.0439(16) Uani 0.4 1 d . . P B 2
C13' C -0.0045(6) 0.5074(16) 0.6426(8) 0.058(3) Uani 0.4 1 d . U P B 2
H13D H -0.047401 0.463252 0.604608 0.087 Uiso 0.4 1 d R U P B 2
H13E H 0.023719 0.456892 0.698109 0.087 Uiso 0.4 1 d R U P B 2
H13F H -0.008771 0.604742 0.653368 0.087 Uiso 0.4 1 d R U P B 2
C22 C 0.20344(13) 0.3835(3) 0.57195(17) 0.0239(6) Uani 1 1 d . U . . .
N1 N 0.18063(12) 0.5779(3) 0.48572(15) 0.0282(5) Uani 1 1 d . . . . .
N2 N 0.33728(12) 0.5688(3) 0.70347(17) 0.0320(6) Uani 1 1 d . . . . .
O2 O 0.20601(11) 0.7639(2) 0.57887(14) 0.0316(5) Uani 1 1 d . . . . .
O1 O 0.11077(18) 0.5797(5) 0.7189(2) 0.0807(11) Uani 1 1 d . . . . .
S1 S 0.31103(4) 0.43994(9) 0.80207(5) 0.0326(2) Uani 1 1 d . . . . .
O3A O 0.0219(11) 0.585(3) 0.5868(15) 0.061(6) Uani 0.2 1 d . U P B 3
C13A C -0.007(2) 0.592(5) 0.637(3) 0.122(15) Uani 0.2 1 d . U P B 3
H13G H -0.054349 0.595903 0.588723 0.183 Uiso 0.2 1 d R U P B 3
H13H H 0.001301 0.540953 0.685973 0.183 Uiso 0.2 1 d R U P B 3
H13I H 0.009491 0.687783 0.655923 0.183 Uiso 0.2 1 d R U P B 3


_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
C1 C6 1.310(6) . ?
C1 C2 1.340(7) . ?
C1 H1A 0.9500 . ?
C2 C3 1.290(7) . ?
C2 H2A 0.9500 . ?
C3 C4 1.406(8) . ?
C3 H3A 0.9500 . ?
C4 C5 1.370(7) . ?
C4 H4A 0.9500 . ?
C5 C6 1.397(7) . ?
C5 H5B 0.9500 . ?
C6 N2 1.422(4) . ?
C7 N2 1.264(4) . ?
C7 C8 1.528(4) . ?
C7 S1 1.765(3) . ?
C8 C22 1.511(4) . ?
C8 C15 1.535(4) . ?
C8 C9 1.538(4) . ?
C9 C11 1.508(4) . ?
C9 C10 1.532(4) . ?
C9 H9A 1.0000 . ?
C10 S1 1.838(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.491(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O1 1.173(5) . ?
C12 O3A 1.27(2) . ?
C12 O3' 1.339(7) . ?
C12 O3 1.507(9) . ?
O3 C13 1.477(13) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 O2 1.217(4) . ?
C15 N1 1.360(4) . ?
C16 N1 1.454(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.379(4) . ?
C17 C22 1.387(4) . ?
C17 N1 1.408(4) . ?
C18 C19 1.397(5) . ?
C18 H18A 0.9500 . ?
C19 C20 1.372(5) . ?
C19 H19A 0.9500 . ?
C20 C21 1.392(4) . ?
C20 H20A 0.9500 . ?
C21 C22 1.382(4) . ?
C21 H21A 0.9500 . ?
C1' C2' 1.402(10) . ?
C1' C6' 1.412(8) . ?
C1' H1'A 0.9500 . ?
C2' C3' 1.287(10) . ?
C2' H2'A 0.9500 . ?
C3' C4' 1.436(9) . ?
C3' H3'A 0.9500 . ?
C4' C5' 1.385(9) . ?
C4' H4'A 0.9500 . ?
C5' C6' 1.387(7) . ?
C5' H5'A 0.9500 . ?
C6' N2 1.422(4) . ?
O3' C13' 1.437(12) . ?
C13' H13D 0.9600 . ?
C13' H13E 0.9601 . ?
C13' H13F 0.9599 . ?
O3A C13A 1.61(5) . ?
C13A H13G 0.9600 . ?
C13A H13H 0.9600 . ?
C13A H13I 0.9600 . ?

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
C6 C1 C2 121.7(7) . . ?
C6 C1 H1A 119.1 . . ?
C2 C1 H1A 119.1 . . ?
C3 C2 C1 124.1(7) . . ?
C3 C2 H2A 118.0 . . ?
C1 C2 H2A 118.0 . . ?
C2 C3 C4 115.3(6) . . ?
C2 C3 H3A 122.4 . . ?
C4 C3 H3A 122.4 . . ?
C5 C4 C3 121.7(7) . . ?
C5 C4 H4A 119.1 . . ?
C3 C4 H4A 119.1 . . ?
C4 C5 C6 117.4(7) . . ?
C4 C5 H5B 121.3 . . ?
C6 C5 H5B 121.3 . . ?
C1 C6 C5 118.7(5) . . ?
C1 C6 N2 121.3(4) . . ?
C5 C6 N2 120.0(4) . . ?
N2 C7 C8 121.6(3) . . ?
N2 C7 S1 128.0(2) . . ?
C8 C7 S1 110.4(2) . . ?
C22 C8 C7 111.4(2) . . ?
C22 C8 C15 102.7(2) . . ?
C7 C8 C15 110.7(2) . . ?
C22 C8 C9 116.8(2) . . ?
C7 C8 C9 104.0(2) . . ?
C15 C8 C9 111.3(2) . . ?
C11 C9 C10 113.2(2) . . ?
C11 C9 C8 114.9(2) . . ?
C10 C9 C8 107.7(2) . . ?
C11 C9 H9A 106.8 . . ?
C10 C9 H9A 106.8 . . ?
C8 C9 H9A 106.8 . . ?
C9 C10 S1 104.89(19) . . ?
C9 C10 H10A 110.8 . . ?
S1 C10 H10A 110.8 . . ?
C9 C10 H10B 110.8 . . ?
S1 C10 H10B 110.8 . . ?
H10A C10 H10B 108.8 . . ?
C12 C11 C9 112.0(3) . . ?
C12 C11 H11A 109.2 . . ?
C9 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C9 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
O1 C12 O3A 118.0(10) . . ?
O1 C12 O3' 111.6(5) . . ?
O1 C12 C11 127.5(4) . . ?
O3A C12 C11 114.3(10) . . ?
O3' C12 C11 111.3(4) . . ?
O1 C12 O3 119.9(5) . . ?
C11 C12 O3 103.8(5) . . ?
C13 O3 C12 111.2(8) . . ?
O3 C13 H13A 107.0 . . ?
O3 C13 H13B 112.1 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.3 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C15 N1 125.7(3) . . ?
O2 C15 C8 126.5(3) . . ?
N1 C15 C8 107.8(2) . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 122.2(3) . . ?
C18 C17 N1 127.8(3) . . ?
C22 C17 N1 110.0(2) . . ?
C17 C18 C19 117.4(3) . . ?
C17 C18 H18A 121.3 . . ?
C19 C18 H18A 121.3 . . ?
C20 C19 C18 121.2(3) . . ?
C20 C19 H19A 119.4 . . ?
C18 C19 H19A 119.4 . . ?
C19 C20 C21 120.5(3) . . ?
C19 C20 H20A 119.8 . . ?
C21 C20 H20A 119.8 . . ?
C22 C21 C20 119.1(3) . . ?
C22 C21 H21A 120.4 . . ?
C20 C21 H21A 120.4 . . ?
C2' C1' C6' 118.8(7) . . ?
C2' C1' H1'A 120.6 . . ?
C6' C1' H1'A 120.6 . . ?
C3' C2' C1' 121.3(7) . . ?
C3' C2' H2'A 119.4 . . ?
C1' C2' H2'A 119.4 . . ?
C2' C3' C4' 120.2(5) . . ?
C2' C3' H3'A 119.9 . . ?
C4' C3' H3'A 119.9 . . ?
C5' C4' C3' 117.2(6) . . ?
C5' C4' H4'A 121.4 . . ?
C3' C4' H4'A 121.4 . . ?
C4' C5' C6' 120.9(6) . . ?
C4' C5' H5'A 119.5 . . ?
C6' C5' H5'A 119.5 . . ?
C5' C6' C1' 118.0(5) . . ?
C5' C6' N2 116.0(4) . . ?
C1' C6' N2 124.3(4) . . ?
C12 O3' C13' 117.5(7) . . ?
O3' C13' H13D 109.1 . . ?
O3' C13' H13E 108.1 . . ?
H13D C13' H13E 109.5 . . ?
O3' C13' H13F 111.2 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 109.5 . . ?
C21 C22 C17 119.5(3) . . ?
C21 C22 C8 132.3(3) . . ?
C17 C22 C8 108.1(2) . . ?
C15 N1 C17 111.3(2) . . ?
C15 N1 C16 123.7(3) . . ?
C17 N1 C16 125.0(3) . . ?
C7 N2 C6' 121.2(3) . . ?
C7 N2 C6 121.2(3) . . ?
C7 S1 C10 94.06(13) . . ?
C12 O3A C13A 109(2) . . ?
O3A C13A H13G 102.5 . . ?
O3A C13A H13H 133.9 . . ?
H13G C13A H13H 109.5 . . ?
O3A C13A H13I 89.2 . . ?
H13G C13A H13I 109.5 . . ?
H13H C13A H13I 109.5 . . ?

_refine_diff_density_max         0.705
_refine_diff_density_min         -0.601
_refine_diff_density_rms         0.074

