# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2021

####################################################################### 
# 
# 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_g22_0m
_audit_block_doi                 10.5517/ccdc.csd.cc21xj7r
_database_code_depnum_ccdc_archive 'CCDC 1904244'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C9NJ05612B 2020
loop_
_audit_author_name
_audit_author_address
'Hamilton Napolitano'
;State University of Goias
Brazil
;
_audit_update_record             
;
2019-03-19 deposited with the CCDC.	2021-03-08 downloaded from the CCDC.
;
_audit_creation_date             2019-03-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            'Sulfonamide chalcone'
_chemical_name_systematic        
(E)-3-(2-chlorophenyl)-1-(2-(phenylsulfonylamine)phenyl)prop-2-en-1-one
_chemical_formula_moiety         'C22 H19 N O4 S'
_chemical_formula_sum            'C22 H19 N O4 S'
_chemical_formula_weight         393.44
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   11.6707(12)
_cell_length_b                   12.5558(13)
_cell_length_c                   13.3311(14)
_cell_angle_alpha                90
_cell_angle_beta                 101.004(3)
_cell_angle_gamma                90
_cell_volume                     1917.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.25
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1418 before and 0.0524 after correction. The Ratio of minimum to maximum transmission is 0.8137. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.295
_exptl_crystal_size_min          0.254
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24455
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.532
_diffrn_reflns_theta_min         2.127
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3122
_reflns_number_total             3952
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3952
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0504
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0551P)²+1.1934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1389
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C16(H16), C2(H2), C22(H22), C18(H18), C13(H13), C5(H5),
 C21(H21), C4(H4), C3(H3), C20(H20), C19(H19), C15(H15), C14(H14)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.093
;
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 0.18240(5) 0.28506(5) 0.20173(5) 0.04068(18) Uani 1 1 d . . . . .
O1 O 0.37135(14) 0.50200(13) 0.11857(14) 0.0517(5) Uani 1 1 d . . . . .
O4 O 0.80349(15) 0.58507(13) 0.11639(15) 0.0523(5) Uani 1 1 d . . . . .
O3 O 0.15797(16) 0.17415(15) 0.19175(14) 0.0572(5) Uani 1 1 d . . . . .
O2 O 0.08812(14) 0.35940(16) 0.18367(14) 0.0571(5) Uani 1 1 d . . . . .
N1 N 0.26591(15) 0.32091(16) 0.12195(14) 0.0391(4) Uani 1 1 d . . . . .
H1 H 0.2462 0.3944 0.1137 0.047 Uiso 1 1 d R . . . .
C11 C 0.47102(18) 0.33836(17) 0.11025(16) 0.0349(5) Uani 1 1 d . . . . .
C17 C 0.26449(18) 0.30823(18) 0.32574(17) 0.0367(5) Uani 1 1 d . . . . .
C12 C 0.37412(18) 0.27308(17) 0.11573(16) 0.0356(5) Uani 1 1 d . . . . .
C10 C 0.46585(19) 0.45639(18) 0.11865(16) 0.0374(5) Uani 1 1 d . . . . .
C9 C 0.5729(2) 0.52042(18) 0.12760(17) 0.0397(5) Uani 1 1 d . . . . .
H9 H 0.6420 0.4881 0.1186 0.048 Uiso 1 1 calc R . . . .
C1 C 0.7762(2) 0.68698(18) 0.13505(16) 0.0378(5) Uani 1 1 d . . . . .
C6 C 0.6625(2) 0.70483(18) 0.15443(17) 0.0385(5) Uani 1 1 d . . . . .
C8 C 0.5719(2) 0.62418(19) 0.14840(17) 0.0412(5) Uani 1 1 d . . . . .
H8 H 0.5012 0.6494 0.1613 0.049 Uiso 1 1 calc R . . . .
C16 C 0.5734(2) 0.28720(19) 0.0952(2) 0.0468(6) Uani 1 1 d . . . . .
H16 H 0.6381 0.3284 0.0895 0.056 Uiso 1 1 calc R . . . .
C2 C 0.8522(2) 0.7718(2) 0.13470(18) 0.0468(6) Uani 1 1 d . . . . .
H2 H 0.9258 0.7600 0.1198 0.056 Uiso 1 1 calc R . . . .
C22 C 0.2909(2) 0.2263(2) 0.3946(2) 0.0482(6) Uani 1 1 d . . . . .
H22 H 0.2671 0.1570 0.3768 0.058 Uiso 1 1 calc R . . . .
C18 C 0.3003(2) 0.4113(2) 0.3516(2) 0.0499(6) Uani 1 1 d . . . . .
H18 H 0.2824 0.4661 0.3042 0.060 Uiso 1 1 calc R . . . .
C13 C 0.3831(2) 0.1633(2) 0.1091(2) 0.0489(6) Uani 1 1 d . . . . .
H13 H 0.3187 0.1207 0.1127 0.059 Uiso 1 1 calc R . . . .
C5 C 0.6343(2) 0.8090(2) 0.1769(2) 0.0488(6) Uani 1 1 d . . . . .
H5 H 0.5607 0.8227 0.1910 0.059 Uiso 1 1 calc R . . . .
C21 C 0.3541(2) 0.2493(3) 0.4916(2) 0.0597(7) Uani 1 1 d . . . . .
H21 H 0.3722 0.1949 0.5394 0.072 Uiso 1 1 calc R . . . .
C4 C 0.7113(3) 0.8923(2) 0.1790(2) 0.0549(7) Uani 1 1 d . . . . .
H4 H 0.6904 0.9606 0.1956 0.066 Uiso 1 1 calc R . . . .
C3 C 0.8196(2) 0.8731(2) 0.15622(19) 0.0517(6) Uani 1 1 d . . . . .
H3 H 0.8713 0.9293 0.1554 0.062 Uiso 1 1 calc R . . . .
C20 C 0.3898(2) 0.3512(3) 0.5173(2) 0.0603(7) Uani 1 1 d . . . . .
H20 H 0.4327 0.3655 0.5821 0.072 Uiso 1 1 calc R . . . .
C19 C 0.3625(3) 0.4321(2) 0.4480(2) 0.0602(7) Uani 1 1 d . . . . .
H19 H 0.3862 0.5014 0.4661 0.072 Uiso 1 1 calc R . . . .
C15 C 0.5812(2) 0.1789(2) 0.0886(2) 0.0575(7) Uani 1 1 d . . . . .
H15 H 0.6501 0.1472 0.0782 0.069 Uiso 1 1 calc R . . . .
C14 C 0.4861(3) 0.1170(2) 0.0974(2) 0.0582(7) Uani 1 1 d . . . . .
H14 H 0.4918 0.0432 0.0953 0.070 Uiso 1 1 calc R . . . .
C7 C 0.9185(2) 0.5633(2) 0.0999(3) 0.0685(8) Uani 1 1 d . . . . .
H7A H 0.9310 0.6001 0.0398 0.103 Uiso 1 1 calc GR . . . .
H7B H 0.9273 0.4881 0.0910 0.103 Uiso 1 1 calc GR . . . .
H7C H 0.9746 0.5871 0.1579 0.103 Uiso 1 1 calc GR . . . .


_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 1.4225(19) . ?
S1 O2 1.4279(18) . ?
S1 N1 1.6369(18) . ?
S1 C17 1.769(2) . ?
O1 C10 1.243(3) . ?
O4 C1 1.353(3) . ?
O4 C7 1.427(3) . ?
N1 C12 1.415(3) . ?
C11 C12 1.410(3) . ?
C11 C10 1.488(3) . ?
C11 C16 1.405(3) . ?
C17 C22 1.374(3) . ?
C17 C18 1.384(3) . ?
C12 C13 1.387(3) . ?
C10 C9 1.471(3) . ?
C9 C8 1.333(3) . ?
C1 C6 1.418(3) . ?
C1 C2 1.386(3) . ?
C6 C8 1.454(3) . ?
C6 C5 1.395(3) . ?
C16 C15 1.367(4) . ?
C2 C3 1.374(4) . ?
C22 C21 1.390(4) . ?
C18 C19 1.375(4) . ?
C13 C14 1.371(4) . ?
C5 C4 1.375(4) . ?
C21 C20 1.369(4) . ?
C4 C3 1.377(4) . ?
C20 C19 1.370(4) . ?
C15 C14 1.379(4) . ?

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 119.33(11) . . ?
O3 S1 N1 110.00(11) . . ?
O3 S1 C17 108.15(11) . . ?
O2 S1 N1 104.23(10) . . ?
O2 S1 C17 108.20(11) . . ?
N1 S1 C17 106.17(10) . . ?
C1 O4 C7 118.1(2) . . ?
C12 N1 S1 124.76(15) . . ?
C12 C11 C10 122.04(19) . . ?
C16 C11 C12 117.0(2) . . ?
C16 C11 C10 120.9(2) . . ?
C22 C17 S1 120.92(19) . . ?
C22 C17 C18 121.0(2) . . ?
C18 C17 S1 118.06(18) . . ?
C11 C12 N1 119.35(19) . . ?
C13 C12 N1 120.3(2) . . ?
C13 C12 C11 120.3(2) . . ?
O1 C10 C11 120.5(2) . . ?
O1 C10 C9 119.2(2) . . ?
C9 C10 C11 120.28(19) . . ?
C8 C9 C10 120.7(2) . . ?
O4 C1 C6 116.38(19) . . ?
O4 C1 C2 123.5(2) . . ?
C2 C1 C6 120.1(2) . . ?
C1 C6 C8 125.1(2) . . ?
C5 C6 C1 117.0(2) . . ?
C5 C6 C8 117.8(2) . . ?
C9 C8 C6 131.1(2) . . ?
C15 C16 C11 122.2(2) . . ?
C3 C2 C1 120.5(2) . . ?
C17 C22 C21 118.5(2) . . ?
C19 C18 C17 119.4(2) . . ?
C14 C13 C12 120.5(2) . . ?
C4 C5 C6 122.5(2) . . ?
C20 C21 C22 120.6(3) . . ?
C5 C4 C3 119.1(2) . . ?
C2 C3 C4 120.7(2) . . ?
C21 C20 C19 120.3(3) . . ?
C20 C19 C18 120.2(3) . . ?
C16 C15 C14 119.4(2) . . ?
C13 C14 C15 120.6(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.95 1.98 2.590(2) 119.7 .
C22 H22 O1 0.93 2.54 3.380(3) 150.6 2_545
C18 H18 O3 0.93 2.70 3.401(3) 132.7 2
C5 H5 O2 0.93 2.67 3.526(3) 153.5 2
C7 H7B O2 0.96 2.60 3.298(4) 129.5 1_655

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_g32_1_0m
_audit_block_doi                 10.5517/ccdc.csd.cc21xj8s
_database_code_depnum_ccdc_archive 'CCDC 1904245'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1007/s00044-019-02384-8 2019
2 10.1039/C9NJ05612B 2020
loop_
_audit_author_name
_audit_author_address
'Hamilton Napolitano'
;State University of Goias
Brazil
;
_audit_update_record             
;
2019-03-19 deposited with the CCDC.	2021-03-08 downloaded from the CCDC.
;
_vrf_mo_g32_1_0m                 
;
RESPONSE: The atom O4 does not vibrate along S1-O4 bond.
;
_audit_creation_date             2019-03-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            'Sulfonamide chalcone'
_chemical_name_systematic        
(E)-3-(2-methoxyphenyl)-1-(2-(phenylsulfonylamine)phenyl)prop-2-en-1-one
_chemical_formula_moiety         'C21 H16 N2 O5 S'
_chemical_formula_sum            'C21 H16 N2 O5 S'
_chemical_formula_weight         408.42
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.0149(16)
_cell_length_b                   7.6562(9)
_cell_length_c                   18.380(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.242(4)
_cell_angle_gamma                90
_cell_volume                     1934.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9812
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.50
_cell_measurement_theta_min      2.26
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.912
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1361 before and 0.0592 after correction. The Ratio of minimum to maximum transmission is 0.8599. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.462
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.095
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            30977
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.829
_diffrn_reflns_theta_min         1.481
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2976
_reflns_number_total             3950
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3950
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0528
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0502P)²+0.7905P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1193
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
C16 \\sim C21 \\sim C20 \\sim C19 \\sim C18 \\sim C17: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08
O4 \\sim S1 \\sim O5: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C7(H7), C8(H8), C14(H14), C13(H13), C12(H12), C4(H4),
 C17(H17), C21(H21), C18(H18), C20(H20), C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.31610(3) 0.19620(9) 0.14857(2) 0.05280(19) Uani 1 1 d . U . . .
O1 O 0.50851(10) 0.2684(3) 0.33653(8) 0.0774(6) Uani 1 1 d . . . . .
O2 O 0.97082(12) 0.5115(3) 0.68939(11) 0.1051(8) Uani 1 1 d . . . . .
O5 O 0.39704(10) 0.2487(3) 0.11688(8) 0.0789(6) Uani 1 1 d . U . . .
O3 O 0.94477(11) 0.5197(3) 0.57105(11) 0.0845(6) Uani 1 1 d . . . . .
N2 N 0.35547(11) 0.2128(3) 0.23723(8) 0.0599(5) Uani 1 1 d . . . . .
H2 H 0.4132 0.2546 0.2506 0.072 Uiso 1 1 calc R . . . .
N1 N 0.91853(12) 0.4908(3) 0.62902(11) 0.0627(5) Uani 1 1 d . . . . .
C2 C 0.81829(13) 0.4271(3) 0.62611(11) 0.0474(5) Uani 1 1 d . . . . .
C1 C 0.75894(13) 0.4051(3) 0.55750(10) 0.0442(5) Uani 1 1 d . . . . .
H1 H 0.7817 0.4315 0.5145 0.053 Uiso 1 1 calc R . . . .
C6 C 0.66458(13) 0.3431(3) 0.55325(10) 0.0417(4) Uani 1 1 d . . . . .
C7 C 0.60336(13) 0.3163(3) 0.47994(10) 0.0466(5) Uani 1 1 d . . . . .
H7 H 0.6312 0.3455 0.4396 0.056 Uiso 1 1 calc R . . . .
C8 C 0.51384(13) 0.2560(3) 0.46413(10) 0.0486(5) Uani 1 1 d . . . . .
H8 H 0.4824 0.2244 0.5023 0.058 Uiso 1 1 calc R . . . .
C9 C 0.46300(13) 0.2381(3) 0.38617(10) 0.0470(5) Uani 1 1 d . . . . .
C10 C 0.35922(12) 0.1836(3) 0.36874(9) 0.0396(4) Uani 1 1 d . . . . .
C15 C 0.30787(12) 0.1680(3) 0.29507(9) 0.0425(5) Uani 1 1 d . . . . .
C14 C 0.21151(13) 0.1114(3) 0.28101(10) 0.0517(5) Uani 1 1 d . . . . .
H14 H 0.1781 0.0990 0.2323 0.062 Uiso 1 1 calc R . . . .
C13 C 0.16546(14) 0.0738(3) 0.33904(11) 0.0548(6) Uani 1 1 d . . . . .
H13 H 0.1009 0.0373 0.3291 0.066 Uiso 1 1 calc R . . . .
C12 C 0.21385(14) 0.0898(3) 0.41136(11) 0.0557(6) Uani 1 1 d . . . . .
H12 H 0.1823 0.0647 0.4502 0.067 Uiso 1 1 calc R . . . .
C11 C 0.30950(14) 0.1431(3) 0.42577(10) 0.0485(5) Uani 1 1 d . . . . .
H11 H 0.3422(15) 0.152(3) 0.4767(12) 0.058 Uiso 1 1 d R . . . .
C5 C 0.63325(15) 0.3062(3) 0.61916(11) 0.0525(5) Uani 1 1 d . . . . .
H5 H 0.5700(17) 0.262(3) 0.6183(12) 0.063 Uiso 1 1 d R . . . .
C4 C 0.69435(16) 0.3296(4) 0.68682(12) 0.0673(7) Uani 1 1 d . . . . .
H4 H 0.6723 0.3039 0.7302 0.081 Uiso 1 1 calc R . . . .
C3 C 0.78816(16) 0.3908(4) 0.69106(12) 0.0622(6) Uani 1 1 d . . . . .
H3 H 0.8343(17) 0.408(3) 0.7384(13) 0.075 Uiso 1 1 d R . . . .
C16 C 0.22328(14) 0.3525(3) 0.12498(9) 0.0467(5) Uani 1 1 d . U . . .
C17 C 0.12758(14) 0.2970(3) 0.10536(12) 0.0556(6) Uani 1 1 d . U . . .
H17 H 0.1131 0.1784 0.1039 0.067 Uiso 1 1 calc R . . . .
C21 C 0.2454(2) 0.5280(4) 0.12535(11) 0.0686(7) Uani 1 1 d . U . . .
H21 H 0.3096 0.5657 0.1372 0.082 Uiso 1 1 calc R . . . .
C18 C 0.05424(18) 0.4178(4) 0.08802(14) 0.0760(8) Uani 1 1 d . U . . .
H18 H -0.0100 0.3808 0.0750 0.091 Uiso 1 1 calc R . . . .
C20 C 0.1693(3) 0.6478(4) 0.10747(14) 0.0850(9) Uani 1 1 d . U . . .
H20 H 0.1825 0.7669 0.1075 0.102 Uiso 1 1 calc R . . . .
C19 C 0.0752(2) 0.5898(5) 0.08989(16) 0.0860(9) Uani 1 1 d . U . . .
H19 H 0.0248 0.6705 0.0791 0.103 Uiso 1 1 calc R . . . .
O4 O 0.27246(11) 0.0286(2) 0.13122(8) 0.0662(4) Uani 1 1 d . 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 O5 1.4300(15) . ?
S1 N2 1.6205(16) . ?
S1 C16 1.759(2) . ?
S1 O4 1.4303(18) . ?
O1 C9 1.233(2) . ?
O2 N1 1.215(2) . ?
O3 N1 1.213(2) . ?
N2 C15 1.403(2) . ?
N1 C2 1.478(2) . ?
C2 C1 1.379(2) . ?
C2 C3 1.370(3) . ?
C1 C6 1.393(2) . ?
C6 C7 1.464(2) . ?
C6 C5 1.395(3) . ?
C7 C8 1.315(3) . ?
C8 C9 1.477(3) . ?
C9 C10 1.487(2) . ?
C10 C15 1.409(2) . ?
C10 C11 1.402(2) . ?
C15 C14 1.393(2) . ?
C14 C13 1.380(3) . ?
C13 C12 1.375(3) . ?
C12 C11 1.377(3) . ?
C5 C4 1.377(3) . ?
C4 C3 1.384(3) . ?
C16 C17 1.386(3) . ?
C16 C21 1.378(3) . ?
C17 C18 1.373(3) . ?
C21 C20 1.397(4) . ?
C18 C19 1.348(4) . ?
C20 C19 1.369(4) . ?

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
O5 S1 N2 104.24(8) . . ?
O5 S1 C16 108.40(11) . . ?
O5 S1 O4 120.00(11) . . ?
N2 S1 C16 106.56(9) . . ?
O4 S1 N2 109.97(10) . . ?
O4 S1 C16 106.97(10) . . ?
C15 N2 S1 128.59(13) . . ?
O2 N1 C2 118.4(2) . . ?
O3 N1 O2 123.09(19) . . ?
O3 N1 C2 118.49(18) . . ?
C1 C2 N1 118.23(18) . . ?
C3 C2 N1 119.18(18) . . ?
C3 C2 C1 122.58(18) . . ?
C2 C1 C6 119.33(17) . . ?
C1 C6 C7 118.62(16) . . ?
C1 C6 C5 118.44(17) . . ?
C5 C6 C7 122.92(17) . . ?
C8 C7 C6 127.97(18) . . ?
C7 C8 C9 120.39(17) . . ?
O1 C9 C8 118.64(17) . . ?
O1 C9 C10 121.25(16) . . ?
C8 C9 C10 120.11(16) . . ?
C15 C10 C9 121.72(15) . . ?
C11 C10 C9 120.59(16) . . ?
C11 C10 C15 117.69(16) . . ?
N2 C15 C10 118.56(15) . . ?
C14 C15 N2 121.47(16) . . ?
C14 C15 C10 119.96(16) . . ?
C13 C14 C15 120.24(17) . . ?
C12 C13 C14 120.79(17) . . ?
C13 C12 C11 119.37(17) . . ?
C12 C11 C10 121.94(18) . . ?
C4 C5 C6 120.81(19) . . ?
C5 C4 C3 120.8(2) . . ?
C2 C3 C4 118.07(19) . . ?
C17 C16 S1 119.16(18) . . ?
C21 C16 S1 120.47(18) . . ?
C21 C16 C17 120.4(2) . . ?
C18 C17 C16 119.8(2) . . ?
C16 C21 C20 118.6(2) . . ?
C19 C18 C17 120.2(3) . . ?
C19 C20 C21 119.9(3) . . ?
C18 C19 C20 121.2(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.86 1.86 2.566(2) 138.0 .
C8 H8 O5 0.93 2.63 3.515(2) 160.3 4_566
C11 H11 O5 0.96(2) 2.65(2) 3.585(2) 163.6(17) 4_566
C5 H5 O5 0.95(2) 2.42(2) 3.329(2) 160.9(19) 4_566
C20 H20 O4 0.93 2.36 3.246(4) 158.5 1_565
C19 H19 O3 0.93 2.62 3.486(4) 156.0 4_475

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
S1 N2 C15 C10 175.95(17) . . . . ?
S1 N2 C15 C14 -5.0(3) . . . . ?
S1 C16 C17 C18 178.91(17) . . . . ?
S1 C16 C21 C20 -178.93(16) . . . . ?
O1 C9 C10 C15 -1.5(3) . . . . ?
O1 C9 C10 C11 177.5(2) . . . . ?
O2 N1 C2 C1 179.5(2) . . . . ?
O2 N1 C2 C3 -1.1(3) . . . . ?
O5 S1 N2 C15 -176.0(2) . . . . ?
O5 S1 C16 C17 139.54(16) . . . . ?
O5 S1 C16 C21 -39.87(18) . . . . ?
O3 N1 C2 C1 -0.6(3) . . . . ?
O3 N1 C2 C3 178.8(2) . . . . ?
N2 S1 C16 C17 -108.78(16) . . . . ?
N2 S1 C16 C21 71.81(17) . . . . ?
N2 C15 C14 C13 -177.8(2) . . . . ?
N1 C2 C1 C6 179.15(19) . . . . ?
N1 C2 C3 C4 -179.3(2) . . . . ?
C2 C1 C6 C7 -178.47(19) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C1 C6 C7 C8 178.5(2) . . . . ?
C1 C6 C5 C4 -0.4(3) . . . . ?
C6 C7 C8 C9 179.9(2) . . . . ?
C6 C5 C4 C3 0.3(4) . . . . ?
C7 C6 C5 C4 178.4(2) . . . . ?
C7 C8 C9 O1 5.3(3) . . . . ?
C7 C8 C9 C10 -175.1(2) . . . . ?
C8 C9 C10 C15 178.9(2) . . . . ?
C8 C9 C10 C11 -2.1(3) . . . . ?
C9 C10 C15 N2 -2.8(3) . . . . ?
C9 C10 C15 C14 178.1(2) . . . . ?
C9 C10 C11 C12 -179.1(2) . . . . ?
C10 C15 C14 C13 1.3(3) . . . . ?
C15 C10 C11 C12 0.0(3) . . . . ?
C15 C14 C13 C12 -0.6(4) . . . . ?
C14 C13 C12 C11 -0.3(4) . . . . ?
C13 C12 C11 C10 0.6(4) . . . . ?
C11 C10 C15 N2 178.16(19) . . . . ?
C11 C10 C15 C14 -0.9(3) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C5 C4 C3 C2 -0.1(4) . . . . ?
C3 C2 C1 C6 -0.2(3) . . . . ?
C16 S1 N2 C15 69.5(2) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
C16 C21 C20 C19 -0.2(4) . . . . ?
C17 C16 C21 C20 1.7(3) . . . . ?
C17 C18 C19 C20 1.3(4) . . . . ?
C21 C16 C17 C18 -1.7(3) . . . . ?
C21 C20 C19 C18 -1.3(4) . . . . ?
O4 S1 N2 C15 -46.1(2) . . . . ?
O4 S1 C16 C17 8.82(17) . . . . ?
O4 S1 C16 C21 -170.60(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
