# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_ug1_2020
_database_code_depnum_ccdc_archive 'CCDC 2067554'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Kazimierczuk'
;Gdansk University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2021-03-02 deposited with the CCDC.	2021-07-23 downloaded from the CCDC.
;

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2020-12-21
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic


#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
_chemical_name_systematic        
;
 4-Amino-N-(2-methoxyphenyl)benzenesulfonamide
;
_chemical_formula_moiety         'C13  H14  N2  O3  S'
_chemical_formula_sum            'C13 H14 N2 O3 S'
_chemical_formula_weight         278.32
_chemical_absolute_configuration unk


#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.7740(9)
_cell_length_b                   12.4266(12)
_cell_length_c                   17.269(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2526.6(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2737
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      26.87
_cell_measurement_wavelength     0.71073
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_F_000             1168

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#


_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.1126
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_number            23827
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.359
_diffrn_reflns_theta_max         29.25
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_Friedel_coverage         0
_reflns_number_total             3403
_reflns_number_gt                2642
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'


#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1066P)²+1.0725P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0037(14)
_refine_ls_number_reflns         3403
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.1682
_refine_ls_wR_factor_gt          0.152
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.106

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.56447(16) 0.76259(15) 0.65725(12) 0.0241(4) Uani 1 1 d . . . . .
C2 C 0.67614(17) 0.75769(16) 0.63035(12) 0.0265(4) Uani 1 1 d . . . . .
H2 H 0.703022 0.809813 0.59452 0.032 Uiso 1 1 calc R U . . .
C3 C 0.74747(18) 0.67699(16) 0.65590(12) 0.0266(4) Uani 1 1 d . . . . .
H3 H 0.823628 0.674208 0.637848 0.032 Uiso 1 1 calc R U . . .
C4 C 0.70827(16) 0.59869(16) 0.70854(12) 0.0251(4) Uani 1 1 d . . . . .
C5 C 0.59654(18) 0.60712(16) 0.73641(12) 0.0283(4) Uani 1 1 d . . . . .
H5 H 0.57002 0.557065 0.773848 0.034 Uiso 1 1 calc R U . . .
C6 C 0.52475(17) 0.68693(16) 0.71027(12) 0.0262(4) Uani 1 1 d . . . . .
H6 H 0.448615 0.690307 0.728327 0.031 Uiso 1 1 calc R U . . .
C7 C 0.38177(16) 0.71828(15) 0.52357(12) 0.0253(4) Uani 1 1 d . . . . .
C8 C 0.28779(18) 0.68649(18) 0.56618(13) 0.0296(4) Uani 1 1 d . . . . .
H8 H 0.256842 0.733424 0.604131 0.036 Uiso 1 1 calc R U . . .
C9 C 0.23866(19) 0.58638(19) 0.55368(13) 0.0332(5) Uani 1 1 d . . . . .
H9 H 0.174311 0.56503 0.583103 0.04 Uiso 1 1 calc R U . . .
C10 C 0.28334(18) 0.51763(17) 0.49838(13) 0.0312(5) Uani 1 1 d . . . . .
H10 H 0.250167 0.44885 0.490314 0.037 Uiso 1 1 calc R U . . .
C11 C 0.37719(18) 0.54940(17) 0.45445(13) 0.0294(4) Uani 1 1 d . . . . .
H11 H 0.407347 0.502521 0.416173 0.035 Uiso 1 1 calc R U . . .
C12 C 0.42627(16) 0.64934(16) 0.46674(12) 0.0255(4) Uani 1 1 d . . . . .
C13 C 0.5524(2) 0.62797(19) 0.36023(14) 0.0341(5) Uani 1 1 d . . . . .
H13A H 0.487901 0.615491 0.325522 0.051 Uiso 1 1 calc R U . . .
H13B H 0.582631 0.55873 0.377944 0.051 Uiso 1 1 calc R U . . .
H13C H 0.611849 0.667456 0.332449 0.051 Uiso 1 1 calc R U . . .
N1 N 0.77832(16) 0.51754(15) 0.73254(12) 0.0316(4) Uani 1 1 d . . . . .
N2 N 0.43293(15) 0.82222(14) 0.53358(11) 0.0261(4) Uani 1 1 d . . . . .
O1 O 0.37459(12) 0.86391(11) 0.66920(9) 0.0286(3) Uani 1 1 d . . . . .
O2 O 0.53541(12) 0.95932(11) 0.60763(9) 0.0290(3) Uani 1 1 d . . . . .
O3 O 0.51581(13) 0.68956(12) 0.42551(9) 0.0308(4) Uani 1 1 d . . . . .
S1 S 0.47361(4) 0.86095(4) 0.62063(3) 0.02397(17) Uani 1 1 d . . . . .
H1A H 0.841(3) 0.499(2) 0.698(2) 0.055(9) Uiso 1 1 d . . . . .
H1B H 0.744(2) 0.472(2) 0.7585(17) 0.036(7) Uiso 1 1 d . . . . .
H2A H 0.485(3) 0.838(3) 0.5047(19) 0.051(9) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.393(3) . ?
C1 C2 1.396(3) . ?
C1 S1 1.743(2) . ?
C2 C3 1.380(3) . ?
C2 H2 0.95 . ?
C3 C4 1.409(3) . ?
C3 H3 0.95 . ?
C4 N1 1.367(3) . ?
C4 C5 1.405(3) . ?
C5 C6 1.379(3) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.386(3) . ?
C7 C12 1.404(3) . ?
C7 N2 1.436(2) . ?
C8 C9 1.389(3) . ?
C8 H8 0.95 . ?
C9 C10 1.385(3) . ?
C9 H9 0.95 . ?
C10 C11 1.397(3) . ?
C10 H10 0.95 . ?
C11 C12 1.386(3) . ?
C11 H11 0.95 . ?
C12 O3 1.367(2) . ?
C13 O3 1.429(3) . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
N1 H1A 0.97(3) . ?
N1 H1B 0.82(3) . ?
N2 S1 1.6494(19) . ?
N2 H2A 0.81(3) . ?
O1 S1 1.4368(15) . ?
O2 S1 1.4401(15) . ?

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 120.37(18) . . ?
C6 C1 S1 120.37(15) . . ?
C2 C1 S1 119.21(15) . . ?
C3 C2 C1 119.89(18) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 120.57(19) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
N1 C4 C5 121.08(19) . . ?
N1 C4 C3 120.48(18) . . ?
C5 C4 C3 118.43(18) . . ?
C6 C5 C4 121.04(19) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 119.65(18) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C8 C7 C12 119.66(19) . . ?
C8 C7 N2 121.83(19) . . ?
C12 C7 N2 118.46(18) . . ?
C7 C8 C9 120.4(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 120 . . ?
C8 C9 H9 120 . . ?
C9 C10 C11 120.02(19) . . ?
C9 C10 H10 120 . . ?
C11 C10 H10 120 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120 . . ?
C10 C11 H11 120 . . ?
O3 C12 C11 124.72(19) . . ?
O3 C12 C7 115.39(17) . . ?
C11 C12 C7 119.87(19) . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 N1 H1A 116.5(19) . . ?
C4 N1 H1B 112(2) . . ?
H1A N1 H1B 123(3) . . ?
C7 N2 S1 119.61(14) . . ?
C7 N2 H2A 117(2) . . ?
S1 N2 H2A 106(2) . . ?
C12 O3 C13 116.60(17) . . ?
O1 S1 O2 118.63(9) . . ?
O1 S1 N2 107.69(9) . . ?
O2 S1 N2 104.62(9) . . ?
O1 S1 C1 107.71(9) . . ?
O2 S1 C1 109.98(9) . . ?
N2 S1 C1 107.71(9) . . ?

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
C6 C1 C2 C3 0.5(3) . . . . ?
S1 C1 C2 C3 -176.78(16) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 N1 178.64(19) . . . . ?
C2 C3 C4 C5 -2.3(3) . . . . ?
N1 C4 C5 C6 -177.9(2) . . . . ?
C3 C4 C5 C6 3.1(3) . . . . ?
C4 C5 C6 C1 -2.1(3) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
S1 C1 C6 C5 177.51(16) . . . . ?
C12 C7 C8 C9 0.9(3) . . . . ?
N2 C7 C8 C9 178.38(19) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C10 C11 C12 O3 -177.90(19) . . . . ?
C10 C11 C12 C7 0.3(3) . . . . ?
C8 C7 C12 O3 177.29(18) . . . . ?
N2 C7 C12 O3 -0.2(3) . . . . ?
C8 C7 C12 C11 -1.0(3) . . . . ?
N2 C7 C12 C11 -178.56(18) . . . . ?
C8 C7 N2 S1 54.5(2) . . . . ?
C12 C7 N2 S1 -128.06(17) . . . . ?
C11 C12 O3 C13 6.9(3) . . . . ?
C7 C12 O3 C13 -171.36(18) . . . . ?
C7 N2 S1 O1 -61.34(17) . . . . ?
C7 N2 S1 O2 171.57(15) . . . . ?
C7 N2 S1 C1 54.57(17) . . . . ?
C6 C1 S1 O1 15.33(19) . . . . ?
C2 C1 S1 O1 -167.37(16) . . . . ?
C6 C1 S1 O2 145.97(17) . . . . ?
C2 C1 S1 O2 -36.72(19) . . . . ?
C6 C1 S1 N2 -100.57(18) . . . . ?
C2 C1 S1 N2 76.73(18) . . . . ?

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
C8 H8 O1 0.95 2.41 3.012(3) 120.9 .
N1 H1A O2 0.97(3) 2.20(3) 3.160(3) 172(3) 8_755
N1 H1B O1 0.82(3) 2.31(3) 3.125(2) 171(3) 3_646


# END of CIF

####################################################################### 
# 
# 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_ug1_2021
_database_code_depnum_ccdc_archive 'CCDC 2067556'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Kazimierczuk'
;Gdansk University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2021-03-15 deposited with the CCDC.	2021-07-23 downloaded from the CCDC.
;
#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2021-02-25
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic


#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 N-(4-(N-(3-methoxyphenyl)sulfamoyl)phenyl)acetamide
;
_chemical_formula_moiety         'C15 H16 N2 O4 S'
_chemical_formula_sum            'C15 H16 N2 O4 S'
_chemical_formula_weight         320.36
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'


_cell_length_a                   12.7104(7)
_cell_length_b                   10.0355(5)
_cell_length_c                   23.7593(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3030.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    18544
_cell_measurement_theta_min      1.76
_cell_measurement_theta_max      27.01
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_number            49198
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.347
_diffrn_reflns_theta_max         29.237
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_Friedel_coverage         0
_reflns_number_total             4090
_reflns_number_gt                3438
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0437P)²+1.2662P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0007(3)
_refine_ls_number_reflns         4090
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.09
_refine_ls_wR_factor_gt          0.0856
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_restrained_S_all      1.06
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.047

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.38490(9) 0.55864(11) 0.59574(5) 0.0198(2) Uani 1 1 d . . . . .
C2 C 0.43393(10) 0.43574(11) 0.59958(6) 0.0240(2) Uani 1 1 d . . . . .
H2 H 0.396846 0.360672 0.613714 0.029 Uiso 1 1 calc R U . . .
C3 C 0.53770(10) 0.42365(12) 0.58257(6) 0.0254(3) Uani 1 1 d . . . . .
H3 H 0.571929 0.339729 0.58521 0.031 Uiso 1 1 calc R U . . .
C4 C 0.59241(9) 0.53313(11) 0.56164(5) 0.0204(2) Uani 1 1 d . . . . .
C5 C 0.54167(10) 0.65587(12) 0.55676(6) 0.0259(3) Uani 1 1 d . . . . .
H5 H 0.577816 0.730434 0.541503 0.031 Uiso 1 1 calc R U . . .
C6 C 0.43816(10) 0.66823(12) 0.57433(6) 0.0266(3) Uani 1 1 d . . . . .
H6 H 0.403574 0.751919 0.571714 0.032 Uiso 1 1 calc R U . . .
C7 C 0.77499(9) 0.60501(12) 0.54012(5) 0.0207(2) Uani 1 1 d . . . . .
C8 C 0.88223(10) 0.54811(13) 0.52857(5) 0.0250(2) Uani 1 1 d . . . . .
H8A H 0.93276 0.620906 0.523541 0.038 Uiso 1 1 calc R U . . .
H8B H 0.879751 0.493927 0.494282 0.038 Uiso 1 1 calc R U . . .
H8C H 0.90411 0.492401 0.560362 0.038 Uiso 1 1 calc R U . . .
C9 C 0.33618(9) 0.65359(12) 0.72000(5) 0.0225(2) Uani 1 1 d . . . . .
C10 C 0.41707(10) 0.74296(14) 0.72998(6) 0.0300(3) Uani 1 1 d . . . . .
H10 H 0.427711 0.817119 0.705786 0.036 Uiso 1 1 calc R U . . .
C11 C 0.48264(12) 0.72201(15) 0.77624(6) 0.0358(3) Uani 1 1 d . . . . .
H11 H 0.537508 0.783635 0.783973 0.043 Uiso 1 1 calc R U . . .
C12 C 0.46898(11) 0.61325(15) 0.81089(6) 0.0329(3) Uani 1 1 d . . . . .
H12 H 0.514468 0.599652 0.842086 0.039 Uiso 1 1 calc R U . . .
C13 C 0.38795(10) 0.52327(13) 0.79985(5) 0.0266(3) Uani 1 1 d . . . . .
C14 C 0.32013(10) 0.54325(12) 0.75466(5) 0.0237(2) Uani 1 1 d . . . . .
H14 H 0.264042 0.482986 0.74755 0.028 Uiso 1 1 calc R U . . .
C15 C 0.30272(14) 0.32021(17) 0.82491(7) 0.0446(4) Uani 1 1 d . . . . .
H15A H 0.314211 0.283823 0.787134 0.067 Uiso 1 1 calc R U . . .
H15B H 0.232643 0.360676 0.82687 0.067 Uiso 1 1 calc R U . . .
H15C H 0.307845 0.248366 0.852715 0.067 Uiso 1 1 calc R U . . .
N1 N 0.69775(8) 0.51196(10) 0.54576(5) 0.0230(2) Uani 1 1 d . . . . .
N2 N 0.26393(8) 0.68000(10) 0.67488(5) 0.0218(2) Uani 1 1 d . . . . .
O1 O 0.19370(7) 0.65023(9) 0.58032(4) 0.02531(19) Uani 1 1 d . . . . .
O2 O 0.21910(7) 0.45228(8) 0.64032(4) 0.02484(19) Uani 1 1 d . . . . .
O3 O 0.38051(8) 0.41882(10) 0.83659(4) 0.0340(2) Uani 1 1 d . . . . .
O4 O 0.75922(7) 0.72493(9) 0.54499(4) 0.0281(2) Uani 1 1 d . . . . .
S1 S 0.25593(2) 0.57951(3) 0.62068(2) 0.01942(9) Uani 1 1 d . . . . .
H1 H 0.7159(13) 0.4264(17) 0.5426(7) 0.029(4) Uiso 1 1 d . . . . .
H2A H 0.2684(13) 0.7578(18) 0.6619(7) 0.032(4) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.3849(16) . ?
C1 C6 1.3880(16) . ?
C1 S1 1.7557(12) . ?
C2 C3 1.3848(17) . ?
C2 H2 0.95 . ?
C3 C4 1.3920(16) . ?
C3 H3 0.95 . ?
C4 C5 1.3952(16) . ?
C4 N1 1.4072(15) . ?
C5 C6 1.3858(17) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 O4 1.2255(15) . ?
C7 N1 1.3616(15) . ?
C7 C8 1.5031(17) . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 C10 1.3848(17) . ?
C9 C14 1.3949(17) . ?
C9 N2 1.4362(16) . ?
C10 C11 1.395(2) . ?
C10 H10 0.95 . ?
C11 C12 1.378(2) . ?
C11 H11 0.95 . ?
C12 C13 1.3946(19) . ?
C12 H12 0.95 . ?
C13 O3 1.3672(16) . ?
C13 C14 1.3916(17) . ?
C14 H14 0.95 . ?
C15 O3 1.4261(18) . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
N1 H1 0.892(17) . ?
N2 S1 1.6388(11) . ?
N2 H2A 0.842(18) . ?
O1 S1 1.4314(9) . ?
O2 S1 1.4377(9) . ?

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 120.68(11) . . ?
C2 C1 S1 120.27(9) . . ?
C6 C1 S1 118.99(9) . . ?
C3 C2 C1 119.17(11) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 120.72(11) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 119.71(11) . . ?
C3 C4 N1 116.87(10) . . ?
C5 C4 N1 123.42(11) . . ?
C6 C5 C4 119.53(11) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 120.17(11) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O4 C7 N1 123.11(11) . . ?
O4 C7 C8 122.59(11) . . ?
N1 C7 C8 114.29(10) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 121.45(12) . . ?
C10 C9 N2 118.88(11) . . ?
C14 C9 N2 119.57(11) . . ?
C9 C10 C11 118.73(13) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C12 C11 C10 120.97(13) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 119.59(13) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
O3 C13 C14 124.07(12) . . ?
O3 C13 C12 115.31(12) . . ?
C14 C13 C12 120.61(12) . . ?
C13 C14 C9 118.64(12) . . ?
C13 C14 H14 120.7 . . ?
C9 C14 H14 120.7 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 N1 C4 127.52(10) . . ?
C7 N1 H1 117.7(11) . . ?
C4 N1 H1 114.4(11) . . ?
C9 N2 S1 120.84(8) . . ?
C9 N2 H2A 113.6(12) . . ?
S1 N2 H2A 106.7(12) . . ?
C13 O3 C15 117.12(11) . . ?
O1 S1 O2 118.54(6) . . ?
O1 S1 N2 104.81(5) . . ?
O2 S1 N2 108.16(6) . . ?
O1 S1 C1 110.42(6) . . ?
O2 S1 C1 107.92(5) . . ?
N2 S1 C1 106.31(5) . . ?

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
C6 C1 C2 C3 0.98(19) . . . . ?
S1 C1 C2 C3 -176.34(10) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C2 C3 C4 C5 -1.2(2) . . . . ?
C2 C3 C4 N1 179.52(12) . . . . ?
C3 C4 C5 C6 1.8(2) . . . . ?
N1 C4 C5 C6 -178.93(12) . . . . ?
C4 C5 C6 C1 -1.1(2) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
S1 C1 C6 C5 177.03(10) . . . . ?
C14 C9 C10 C11 -0.8(2) . . . . ?
N2 C9 C10 C11 175.55(12) . . . . ?
C9 C10 C11 C12 1.3(2) . . . . ?
C10 C11 C12 C13 -0.5(2) . . . . ?
C11 C12 C13 O3 -179.85(13) . . . . ?
C11 C12 C13 C14 -0.8(2) . . . . ?
O3 C13 C14 C9 -179.76(12) . . . . ?
C12 C13 C14 C9 1.27(19) . . . . ?
C10 C9 C14 C13 -0.47(19) . . . . ?
N2 C9 C14 C13 -176.78(11) . . . . ?
O4 C7 N1 C4 -5.1(2) . . . . ?
C8 C7 N1 C4 173.72(11) . . . . ?
C3 C4 N1 C7 -159.19(12) . . . . ?
C5 C4 N1 C7 21.5(2) . . . . ?
C10 C9 N2 S1 116.17(12) . . . . ?
C14 C9 N2 S1 -67.42(14) . . . . ?
C14 C13 O3 C15 4.6(2) . . . . ?
C12 C13 O3 C15 -176.36(14) . . . . ?
C9 N2 S1 O1 -168.64(9) . . . . ?
C9 N2 S1 O2 64.00(10) . . . . ?
C9 N2 S1 C1 -51.68(11) . . . . ?
C2 C1 S1 O1 -133.64(10) . . . . ?
C6 C1 S1 O1 48.99(12) . . . . ?
C2 C1 S1 O2 -2.63(12) . . . . ?
C6 C1 S1 O2 180.00(10) . . . . ?
C2 C1 S1 N2 113.21(11) . . . . ?
C6 C1 S1 N2 -64.16(11) . . . . ?

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
_geom_hbond_publ_flag

N1 H1 O4 0.892(17) 2.047(17) 2.9320(14) 171.1(15) 8_755 yes
N2 H2A O2 0.842(18) 2.024(18) 2.8614(14) 173.2(17) 8_665 yes


# END of CIF
####################################################################### 
# 
# 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_ug2_2020
_database_code_depnum_ccdc_archive 'CCDC 2067555'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Kazimierczuk'
;Gdansk University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2021-03-02 deposited with the CCDC.	2021-07-23 downloaded from the CCDC.
;

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2020-12-21
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic


#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
_chemical_name_systematic        
;
 4-Amino-N-(3-methoxyphenyl)benzenesulfonamide
;

_chemical_formula_moiety         'C13  H14  N2  O3  S'
_chemical_formula_sum            'C13 H14 N2 O3 S'
_chemical_formula_weight         278.32
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'


_cell_length_a                   6.0734(4)
_cell_length_b                   15.4472(10)
_cell_length_c                   27.066(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2539.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4620
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      27.95
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0111
_diffrn_reflns_number            32247
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.637
_diffrn_reflns_theta_max         29.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_reflns_Friedel_coverage         0
_reflns_number_total             3418
_reflns_number_gt                3073
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0431P)²+1.4252P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3418
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0852
_refine_ls_wR_factor_gt          0.0816
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_restrained_S_all      1.03
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.05

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.43254(18) 0.43963(7) 0.67788(4) 0.0165(2) Uani 1 1 d . . . . .
C2 C 0.63898(18) 0.45165(7) 0.69955(4) 0.0187(2) Uani 1 1 d . . . . .
H2 H 0.72038 0.403359 0.711338 0.022 Uiso 1 1 calc R U . . .
C3 C 0.72400(19) 0.53437(7) 0.70373(4) 0.0195(2) Uani 1 1 d . . . . .
H3 H 0.86383 0.542804 0.718703 0.023 Uiso 1 1 calc R U . . .
C4 C 0.60546(19) 0.60606(7) 0.68603(4) 0.0175(2) Uani 1 1 d . . . . .
C5 C 0.39949(19) 0.59271(7) 0.66376(4) 0.0194(2) Uani 1 1 d . . . . .
H5 H 0.318724 0.64067 0.651345 0.023 Uiso 1 1 calc R U . . .
C6 C 0.31327(18) 0.50985(7) 0.65980(4) 0.0184(2) Uani 1 1 d . . . . .
H6 H 0.173571 0.501033 0.644835 0.022 Uiso 1 1 calc R U . . .
C7 C 0.48780(18) 0.31609(7) 0.58195(4) 0.0168(2) Uani 1 1 d . . . . .
C8 C 0.68924(18) 0.30012(8) 0.55874(4) 0.0200(2) Uani 1 1 d . . . . .
H8 H 0.803347 0.270309 0.575676 0.024 Uiso 1 1 calc R U . . .
C9 C 0.7201(2) 0.32845(8) 0.51060(4) 0.0215(2) Uani 1 1 d . . . . .
H9 H 0.85589 0.316803 0.494486 0.026 Uiso 1 1 calc R U . . .
C10 C 0.5565(2) 0.37361(8) 0.48537(4) 0.0211(2) Uani 1 1 d . . . . .
H10 H 0.580142 0.393148 0.452519 0.025 Uiso 1 1 calc R U . . .
C11 C 0.35770(19) 0.38953(7) 0.50925(4) 0.0189(2) Uani 1 1 d . . . . .
C12 C 0.32156(18) 0.36014(7) 0.55754(4) 0.0181(2) Uani 1 1 d . . . . .
H12 H 0.184409 0.370316 0.573384 0.022 Uiso 1 1 calc R U . . .
C13 C 0.1990(2) 0.45896(9) 0.43883(4) 0.0272(3) Uani 1 1 d . . . . .
H13A H 0.219034 0.408049 0.417703 0.041 Uiso 1 1 calc R U . . .
H13B H 0.325176 0.497935 0.434938 0.041 Uiso 1 1 calc R U . . .
H13C H 0.063811 0.489268 0.429285 0.041 Uiso 1 1 calc R U . . .
N1 N 0.69409(18) 0.68914(7) 0.68928(4) 0.0215(2) Uani 1 1 d . . . . .
N2 N 0.45733(17) 0.28289(6) 0.63075(4) 0.01806(19) Uani 1 1 d . . . . .
O1 O 0.37532(15) 0.28789(5) 0.71848(3) 0.02276(18) Uani 1 1 d . . . . .
O2 O 0.09681(14) 0.34242(5) 0.65946(3) 0.02137(18) Uani 1 1 d . . . . .
O3 O 0.18315(14) 0.43224(6) 0.48916(3) 0.02447(19) Uani 1 1 d . . . . .
S1 S 0.32378(4) 0.33486(2) 0.67398(2) 0.01650(8) Uani 1 1 d . . . . .
H1B H 0.786(3) 0.6968(12) 0.7152(7) 0.037(5) Uiso 1 1 d . . . . .
H2A H 0.568(3) 0.2545(11) 0.6427(6) 0.030(4) Uiso 1 1 d . . . . .
H1A H 0.601(3) 0.7303(12) 0.6872(6) 0.032(4) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.3931(15) . ?
C1 C2 1.3967(15) . ?
C1 S1 1.7511(11) . ?
C2 C3 1.3828(16) . ?
C2 H2 0.95 . ?
C3 C4 1.4051(16) . ?
C3 H3 0.95 . ?
C4 N1 1.3944(15) . ?
C4 C5 1.4038(16) . ?
C5 C6 1.3870(16) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C12 1.3853(15) . ?
C7 C8 1.3972(15) . ?
C7 N2 1.4289(14) . ?
C8 C9 1.3872(16) . ?
C8 H8 0.95 . ?
C9 C10 1.3931(17) . ?
C9 H9 0.95 . ?
C10 C11 1.3913(16) . ?
C10 H10 0.95 . ?
C11 O3 1.3618(14) . ?
C11 C12 1.4008(15) . ?
C12 H12 0.95 . ?
C13 O3 1.4267(14) . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
N1 H1B 0.904(19) . ?
N1 H1A 0.853(19) . ?
N2 S1 1.6344(10) . ?
N2 H2A 0.865(18) . ?
O1 S1 1.4405(9) . ?
O2 S1 1.4382(9) . ?

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 120.72(10) . . ?
C6 C1 S1 120.15(9) . . ?
C2 C1 S1 119.13(8) . . ?
C3 C2 C1 119.49(10) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.61(11) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
N1 C4 C5 120.42(10) . . ?
N1 C4 C3 120.40(11) . . ?
C5 C4 C3 119.15(10) . . ?
C6 C5 C4 120.35(10) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 119.67(10) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C12 C7 C8 120.69(10) . . ?
C12 C7 N2 121.52(10) . . ?
C8 C7 N2 117.75(10) . . ?
C9 C8 C7 119.02(11) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 121.46(11) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C11 C10 C9 118.68(11) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
O3 C11 C10 125.14(10) . . ?
O3 C11 C12 114.05(10) . . ?
C10 C11 C12 120.80(11) . . ?
C7 C12 C11 119.34(10) . . ?
C7 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 N1 H1B 114.1(12) . . ?
C4 N1 H1A 115.1(12) . . ?
H1B N1 H1A 111.4(17) . . ?
C7 N2 S1 123.34(8) . . ?
C7 N2 H2A 115.4(11) . . ?
S1 N2 H2A 111.5(11) . . ?
C11 O3 C13 117.96(10) . . ?
O2 S1 O1 118.53(5) . . ?
O2 S1 N2 108.66(5) . . ?
O1 S1 N2 104.08(5) . . ?
O2 S1 C1 107.64(5) . . ?
O1 S1 C1 109.46(5) . . ?
N2 S1 C1 108.05(5) . . ?

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
C6 C1 C2 C3 0.97(16) . . . . ?
S1 C1 C2 C3 -178.63(9) . . . . ?
C1 C2 C3 C4 -0.52(17) . . . . ?
C2 C3 C4 N1 -178.51(10) . . . . ?
C2 C3 C4 C5 -0.30(17) . . . . ?
N1 C4 C5 C6 178.90(11) . . . . ?
C3 C4 C5 C6 0.69(16) . . . . ?
C4 C5 C6 C1 -0.25(17) . . . . ?
C2 C1 C6 C5 -0.59(17) . . . . ?
S1 C1 C6 C5 179.01(9) . . . . ?
C12 C7 C8 C9 -0.51(17) . . . . ?
N2 C7 C8 C9 177.35(10) . . . . ?
C7 C8 C9 C10 1.13(17) . . . . ?
C8 C9 C10 C11 -0.59(17) . . . . ?
C9 C10 C11 O3 -179.59(11) . . . . ?
C9 C10 C11 C12 -0.58(17) . . . . ?
C8 C7 C12 C11 -0.62(16) . . . . ?
N2 C7 C12 C11 -178.40(10) . . . . ?
O3 C11 C12 C7 -179.70(10) . . . . ?
C10 C11 C12 C7 1.18(17) . . . . ?
C12 C7 N2 S1 -39.58(15) . . . . ?
C8 C7 N2 S1 142.58(9) . . . . ?
C10 C11 O3 C13 3.58(17) . . . . ?
C12 C11 O3 C13 -175.50(10) . . . . ?
C7 N2 S1 O2 65.08(10) . . . . ?
C7 N2 S1 O1 -167.73(9) . . . . ?
C7 N2 S1 C1 -51.43(10) . . . . ?
C6 C1 S1 O2 -10.68(11) . . . . ?
C2 C1 S1 O2 168.93(8) . . . . ?
C6 C1 S1 O1 -140.77(9) . . . . ?
C2 C1 S1 O1 38.84(10) . . . . ?
C6 C1 S1 N2 106.50(10) . . . . ?
C2 C1 S1 N2 -73.90(10) . . . . ?

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
C12 H12 O2 0.95 2.43 3.0899(14) 126.6 .
N1 H1B O1 0.904(19) 2.484(19) 2.9559(13) 113.0(14) 3_656
N1 H1B O1 0.904(19) 2.493(19) 3.1289(14) 127.7(15) 8_765
N2 H2A N1 0.865(18) 2.167(18) 3.0148(15) 166.4(16) 8_755
N1 H1A O2 0.853(19) 2.237(19) 3.0626(14) 162.8(16) 8_665
C12 H12 O2 0.95 2.43 3.0899(14) 126.6 .
N1 H1B O1 0.904(19) 2.484(19) 2.9559(13) 113.0(14) 3_656
N1 H1B O1 0.904(19) 2.493(19) 3.1289(14) 127.7(15) 8_765
N2 H2A N1 0.865(18) 2.167(18) 3.0148(15) 166.4(16) 8_755
N1 H1A O2 0.853(19) 2.237(19) 3.0626(14) 162.8(16) 8_665


# END of CIF
####################################################################### 
# 
# 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_ug2_2021
_database_code_depnum_ccdc_archive 'CCDC 2067557'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Kazimierczuk'
;Gdansk University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2021-03-15 deposited with the CCDC.	2021-07-23 downloaded from the CCDC.
;
#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2021-02-25
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic


#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 N-(4-(N-(2-methoxyphenyl)sulfamoyl)phenyl)acetamide
;
_chemical_formula_moiety         'C15  H16  N2  O4  S1'
_chemical_formula_sum            'C15 H16 N2 O4 S'
_chemical_formula_weight         320.36
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'



_cell_length_a                   15.6551(11)
_cell_length_b                   11.7852(7)
_cell_length_c                   16.3034(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3008.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    18333
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.01
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#


_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_number            24544
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.498
_diffrn_reflns_theta_max         29.256
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_reflns_Friedel_coverage         0
_reflns_number_total             4030
_reflns_number_gt                3665
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0435P)²+1.3967P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4030
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.086
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.05

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.48748(6) 0.31362(9) 0.36072(6) 0.01576(19) Uani 1 1 d . . . . .
C2 C 0.50590(7) 0.23699(9) 0.29818(7) 0.0195(2) Uani 1 1 d . . . . .
H2 H 0.5611 0.235048 0.274019 0.023 Uiso 1 1 calc R U . . .
C3 C 0.44254(7) 0.16370(10) 0.27176(7) 0.0209(2) Uani 1 1 d . . . . .
H3 H 0.454537 0.110956 0.229229 0.025 Uiso 1 1 calc R U . . .
C4 C 0.36102(7) 0.16635(9) 0.30694(6) 0.01707(19) Uani 1 1 d . . . . .
C5 C 0.34369(7) 0.24234(10) 0.37088(7) 0.0212(2) Uani 1 1 d . . . . .
H5 H 0.288843 0.243753 0.395784 0.025 Uiso 1 1 calc R U . . .
C6 C 0.40726(7) 0.31544(10) 0.39748(7) 0.0208(2) Uani 1 1 d . . . . .
H6 H 0.396037 0.366986 0.440967 0.025 Uiso 1 1 calc R U . . .
C7 C 0.21364(7) 0.08959(10) 0.28795(7) 0.0225(2) Uani 1 1 d . . . . .
C8 C 0.16736(8) 0.00040(11) 0.23891(8) 0.0270(2) Uani 1 1 d . . . . .
H8A H 0.111142 -0.013573 0.263359 0.04 Uiso 1 1 calc R U . . .
H8B H 0.200625 -0.070042 0.239152 0.04 Uiso 1 1 calc R U . . .
H8C H 0.160187 0.026776 0.182324 0.04 Uiso 1 1 calc R U . . .
C9 C 0.64154(7) 0.25612(9) 0.48366(6) 0.0173(2) Uani 1 1 d . . . . .
C10 C 0.60064(7) 0.17335(9) 0.53114(7) 0.0212(2) Uani 1 1 d . . . . .
C11 C 0.63835(9) 0.06680(10) 0.54020(8) 0.0310(3) Uani 1 1 d . . . . .
H11 H 0.611837 0.010571 0.573289 0.037 Uiso 1 1 calc R U . . .
C12 C 0.71497(10) 0.04343(11) 0.50050(9) 0.0349(3) Uani 1 1 d . . . . .
H12 H 0.740766 -0.028987 0.506952 0.042 Uiso 1 1 calc R U . . .
C13 C 0.75406(8) 0.12397(12) 0.45188(8) 0.0311(3) Uani 1 1 d . . . . .
H13 H 0.805533 0.106182 0.423822 0.037 Uiso 1 1 calc R U . . .
C14 C 0.71779(7) 0.23171(10) 0.44398(7) 0.0231(2) Uani 1 1 d . . . . .
H14 H 0.745185 0.287997 0.411617 0.028 Uiso 1 1 calc R U . . .
C15 C 0.48023(11) 0.12420(12) 0.61287(9) 0.0382(3) Uani 1 1 d . . . . .
H15A H 0.467784 0.057721 0.578795 0.057 Uiso 1 1 calc R U . . .
H15B H 0.426573 0.157319 0.632515 0.057 Uiso 1 1 calc R U . . .
H15C H 0.515197 0.101216 0.659875 0.057 Uiso 1 1 calc R U . . .
N1 N 0.30034(6) 0.09026(8) 0.27560(6) 0.01955(19) Uani 1 1 d . . . . .
N2 N 0.60465(6) 0.36736(7) 0.47985(5) 0.01589(17) Uani 1 1 d . . . . .
O1 O 0.52525(5) 0.51846(6) 0.41012(5) 0.01994(16) Uani 1 1 d . . . . .
O2 O 0.63300(5) 0.40844(6) 0.33288(5) 0.02025(16) Uani 1 1 d . . . . .
O3 O 0.52549(5) 0.20615(7) 0.56549(5) 0.02563(18) Uani 1 1 d . . . . .
O4 O 0.17660(6) 0.15546(10) 0.33283(7) 0.0416(3) Uani 1 1 d . . . . .
S1 S 0.56527(2) 0.41115(2) 0.39271(2) 0.01489(8) Uani 1 1 d . . . . .
H1 H 0.3198(10) 0.0424(14) 0.2431(10) 0.030(4) Uiso 1 1 d . . . . .
H2A H 0.5718(10) 0.3851(14) 0.5206(10) 0.027(4) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.3916(14) . ?
C1 C2 1.3922(14) . ?
C1 S1 1.7538(10) . ?
C2 C3 1.3840(15) . ?
C2 H2 0.95 . ?
C3 C4 1.3995(14) . ?
C3 H3 0.95 . ?
C4 C5 1.4008(15) . ?
C4 N1 1.4028(13) . ?
C5 C6 1.3859(15) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 O4 1.2142(15) . ?
C7 N1 1.3721(14) . ?
C7 C8 1.5065(16) . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 C14 1.3879(15) . ?
C9 C10 1.4002(15) . ?
C9 N2 1.4339(13) . ?
C10 O3 1.3592(14) . ?
C10 C11 1.3954(16) . ?
C11 C12 1.391(2) . ?
C11 H11 0.95 . ?
C12 C13 1.380(2) . ?
C12 H12 0.95 . ?
C13 C14 1.3968(17) . ?
C13 H13 0.95 . ?
C14 H14 0.95 . ?
C15 O3 1.4254(15) . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
N1 H1 0.832(17) . ?
N2 S1 1.6325(9) . ?
N2 H2A 0.866(16) . ?
O1 S1 1.4397(8) . ?
O2 S1 1.4411(8) . ?

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 120.82(10) . . ?
C6 C1 S1 119.23(8) . . ?
C2 C1 S1 119.93(8) . . ?
C3 C2 C1 118.97(10) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 120.80(10) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 119.72(10) . . ?
C3 C4 N1 117.01(9) . . ?
C5 C4 N1 123.27(10) . . ?
C6 C5 C4 119.42(10) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 120.24(10) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O4 C7 N1 123.87(11) . . ?
O4 C7 C8 122.42(11) . . ?
N1 C7 C8 113.70(10) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 120.43(10) . . ?
C14 C9 N2 121.05(10) . . ?
C10 C9 N2 118.47(9) . . ?
O3 C10 C11 125.35(11) . . ?
O3 C10 C9 115.18(9) . . ?
C11 C10 C9 119.47(11) . . ?
C12 C11 C10 119.60(13) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C13 C12 C11 120.91(11) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 119.87(12) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C9 C14 C13 119.68(12) . . ?
C9 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 N1 C4 128.32(10) . . ?
C7 N1 H1 116.9(11) . . ?
C4 N1 H1 114.7(11) . . ?
C9 N2 S1 118.61(7) . . ?
C9 N2 H2A 115.3(11) . . ?
S1 N2 H2A 111.5(10) . . ?
C10 O3 C15 117.45(10) . . ?
O1 S1 O2 118.23(5) . . ?
O1 S1 N2 105.69(5) . . ?
O2 S1 N2 107.71(5) . . ?
O1 S1 C1 109.40(5) . . ?
O2 S1 C1 107.16(5) . . ?
N2 S1 C1 108.29(5) . . ?

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
C6 C1 C2 C3 1.26(17) . . . . ?
S1 C1 C2 C3 -177.55(8) . . . . ?
C1 C2 C3 C4 0.18(17) . . . . ?
C2 C3 C4 C5 -1.38(17) . . . . ?
C2 C3 C4 N1 179.06(10) . . . . ?
C3 C4 C5 C6 1.15(17) . . . . ?
N1 C4 C5 C6 -179.33(11) . . . . ?
C4 C5 C6 C1 0.27(18) . . . . ?
C2 C1 C6 C5 -1.49(17) . . . . ?
S1 C1 C6 C5 177.33(9) . . . . ?
C14 C9 C10 O3 -178.56(10) . . . . ?
N2 C9 C10 O3 3.94(14) . . . . ?
C14 C9 C10 C11 1.76(16) . . . . ?
N2 C9 C10 C11 -175.74(10) . . . . ?
O3 C10 C11 C12 178.92(11) . . . . ?
C9 C10 C11 C12 -1.44(17) . . . . ?
C10 C11 C12 C13 -0.35(19) . . . . ?
C11 C12 C13 C14 1.83(18) . . . . ?
C10 C9 C14 C13 -0.30(16) . . . . ?
N2 C9 C14 C13 177.14(10) . . . . ?
C12 C13 C14 C9 -1.49(17) . . . . ?
O4 C7 N1 C4 -3.4(2) . . . . ?
C8 C7 N1 C4 175.30(11) . . . . ?
C3 C4 N1 C7 -166.78(11) . . . . ?
C5 C4 N1 C7 13.68(18) . . . . ?
C14 C9 N2 S1 69.60(12) . . . . ?
C10 C9 N2 S1 -112.91(10) . . . . ?
C11 C10 O3 C15 -1.79(17) . . . . ?
C9 C10 O3 C15 178.56(10) . . . . ?
C9 N2 S1 O1 173.91(8) . . . . ?
C9 N2 S1 O2 -58.82(9) . . . . ?
C9 N2 S1 C1 56.76(9) . . . . ?
C6 C1 S1 O1 -37.45(10) . . . . ?
C2 C1 S1 O1 141.38(9) . . . . ?
C6 C1 S1 O2 -166.78(9) . . . . ?
C2 C1 S1 O2 12.05(10) . . . . ?
C6 C1 S1 N2 77.28(10) . . . . ?
C2 C1 S1 N2 -103.89(9) . . . . ?

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
_geom_hbond_publ_flag

N1 H1 O2 0.832(17) 2.138(17) 2.9679(12) 175.0(16) 3_645 yes
N2 H2A O1 0.866(16) 2.208(16) 3.0272(12) 157.7(15) 5_666 yes


# END of CIF
