# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SS1_54
_database_code_depnum_ccdc_archive 'CCDC 2290032'
loop_
_audit_author_name
_audit_author_address
'Matteo Lusi'
;University of Limerick
Ireland
;
_audit_update_record             
;
2023-08-22 deposited with the CCDC.	2023-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'Chloropropamide Tolbutamide'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10.91 H15.28 Cl0.54 N2 O3 S'
_chemical_formula_weight         273.86

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   20.1171(17)
_cell_length_b                   7.5762(7)
_cell_length_c                   9.1129(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1388.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    342
_cell_measurement_theta_min      4
_cell_measurement_theta_max      40

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.338
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6901
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32127
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.873
_diffrn_reflns_theta_max         25.427
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2549
_reflns_number_gt                2218
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0477P)²+0.2142P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 948 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2549
_refine_ls_number_parameters     183
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0926
_refine_ls_wR_factor_gt          0.0869
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S01 S 0.39664(4) 0.33756(12) 0.46500(9) 0.0577(3) Uani 1 1 d . . . . .
Cl1 Cl 0.2354(3) 1.0306(7) 0.5804(7) 0.117(2) Uani 0.544(10) 1 d D . P A 1
O3 O 0.40527(13) 0.2434(4) 0.5986(3) 0.0695(7) Uani 1 1 d . . . . .
O1 O 0.50276(14) 0.5356(4) 0.6134(3) 0.0761(8) Uani 1 1 d . . . . .
O2 O 0.36696(15) 0.2492(4) 0.3433(3) 0.0695(8) Uani 1 1 d . . . . .
N2 N 0.54875(16) 0.6189(4) 0.3975(3) 0.0622(8) Uani 1 1 d . . . . .
H2 H 0.5514 0.5975 0.3050 0.075 Uiso 1 1 calc R U . . .
N1 N 0.46830(15) 0.4046(5) 0.4020(3) 0.0591(8) Uani 1 1 d . . . . .
C8 C 0.50774(16) 0.5240(5) 0.4788(3) 0.0567(8) Uani 1 1 d . . . . .
C5 C 0.35237(18) 0.5329(6) 0.5024(3) 0.0595(9) Uani 1 1 d . . . . .
C9 C 0.58944(19) 0.7587(5) 0.4600(5) 0.0710(10) Uani 1 1 d . . . . .
H9A H 0.6291 0.7726 0.4007 0.085 Uiso 1 1 calc R U . . .
H9B H 0.6033 0.7238 0.5577 0.085 Uiso 1 1 calc R U . . .
C6 C 0.3560(2) 0.6740(6) 0.4074(5) 0.0754(12) Uani 1 1 d . . . . .
H6 H 0.3823 0.6661 0.3237 0.091 Uiso 1 1 calc R U . . .
C7 C 0.3212(3) 0.8264(6) 0.4352(6) 0.0838(13) Uani 1 1 d . . . . .
H7 H 0.3238 0.9215 0.3709 0.101 Uiso 1 1 calc R U . . .
C2 C 0.2823(2) 0.8367(6) 0.5595(6) 0.0834(13) Uani 1 1 d D . . . .
C4 C 0.3138(2) 0.5430(7) 0.6266(5) 0.0850(13) Uani 1 1 d . . . . .
H4 H 0.3120 0.4488 0.6919 0.102 Uiso 1 1 calc R U . . .
C3 C 0.2781(3) 0.6937(8) 0.6530(6) 0.0986(17) Uani 1 1 d . . . . .
H3 H 0.2506 0.6998 0.7350 0.118 Uiso 1 1 calc R U . . .
C10 C 0.5541(4) 0.9336(7) 0.4693(10) 0.133(2) Uani 1 1 d . . . . .
H10A H 0.5407 0.9701 0.3717 0.159 Uiso 1 1 calc R U . . .
H10B H 0.5144 0.9206 0.5285 0.159 Uiso 1 1 calc R U . . .
C11 C 0.5978(7) 1.0737(11) 0.5357(15) 0.184(5) Uani 1 1 d . . . . .
H11A H 0.5710 1.1538 0.5938 0.221 Uiso 1 1 calc R U . A 2
H11B H 0.6303 1.0191 0.6001 0.221 Uiso 1 1 calc R U . A 2
H1 H 0.4718(19) 0.399(5) 0.315(5) 0.060(11) Uiso 1 1 d . . . . .
C12 C 0.625(2) 1.152(5) 0.445(6) 0.28(3) Uani 0.456(10) 1 d . . P A 2
H12A H 0.5935 1.1879 0.3714 0.426 Uiso 0.456(10) 1 calc R U P A 2
H12B H 0.6582 1.0779 0.4002 0.426 Uiso 0.456(10) 1 calc R U P A 2
H12C H 0.6458 1.2540 0.4864 0.426 Uiso 0.456(10) 1 calc R U P A 2
C1 C 0.2510(11) 1.021(3) 0.647(3) 0.088(6) Uani 0.456(10) 1 d D . P A 2
H1A H 0.2437 1.1134 0.5766 0.132 Uiso 0.456(10) 1 calc R U P A 2
H1B H 0.2823 1.0611 0.7197 0.132 Uiso 0.456(10) 1 calc R U P A 2
H1C H 0.2097 0.9921 0.6941 0.132 Uiso 0.456(10) 1 calc R U P A 2
H11 H 0.620(5) 1.136(18) 0.448(11) 0.05(3) Uiso 0.544(10) 1 d . . P A 1


_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
S01 O3 1.422(3) . ?
S01 O2 1.426(3) . ?
S01 N1 1.633(3) . ?
S01 C5 1.760(4) . ?
Cl1 C2 1.757(7) . ?
O1 C8 1.234(4) . ?
N2 C8 1.322(4) . ?
N2 C9 1.455(5) . ?
N2 H2 0.8600 . ?
N1 C8 1.392(5) . ?
N1 H1 0.80(4) . ?
C5 C4 1.375(5) . ?
C5 C6 1.378(5) . ?
C9 C10 1.506(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C6 C7 1.374(6) . ?
C6 H6 0.9300 . ?
C7 C2 1.379(7) . ?
C7 H7 0.9300 . ?
C2 C3 1.381(7) . ?
C2 C1 1.730(18) . ?
C4 C3 1.370(7) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C10 C11 1.505(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.16(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11 1.03(13) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S01 O2 118.78(16) . . ?
O3 S01 N1 110.46(17) . . ?
O2 S01 N1 104.00(16) . . ?
O3 S01 C5 108.55(17) . . ?
O2 S01 C5 109.45(18) . . ?
N1 S01 C5 104.67(18) . . ?
C8 N2 C9 121.8(3) . . ?
C8 N2 H2 119.1 . . ?
C9 N2 H2 119.1 . . ?
C8 N1 S01 121.9(2) . . ?
C8 N1 H1 119(3) . . ?
S01 N1 H1 114(3) . . ?
O1 C8 N2 124.7(3) . . ?
O1 C8 N1 120.0(3) . . ?
N2 C8 N1 115.3(3) . . ?
C4 C5 C6 120.3(4) . . ?
C4 C5 S01 119.5(3) . . ?
C6 C5 S01 120.3(3) . . ?
N2 C9 C10 113.4(4) . . ?
N2 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
N2 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C7 C6 C5 120.6(4) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C2 119.2(4) . . ?
C6 C7 H7 120.4 . . ?
C2 C7 H7 120.4 . . ?
C7 C2 C3 119.9(4) . . ?
C7 C2 C1 129.2(9) . . ?
C3 C2 C1 109.0(9) . . ?
C7 C2 Cl1 116.2(5) . . ?
C3 C2 Cl1 123.7(4) . . ?
C3 C4 C5 119.2(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C3 C2 120.8(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C11 C10 C9 111.6(6) . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C10 110(3) . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C10 C11 H11 105(7) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

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
O3 S01 N1 C8 -63.2(4) . . . . ?
O2 S01 N1 C8 168.3(3) . . . . ?
C5 S01 N1 C8 53.5(3) . . . . ?
C9 N2 C8 O1 -4.6(6) . . . . ?
C9 N2 C8 N1 175.2(3) . . . . ?
S01 N1 C8 O1 25.5(5) . . . . ?
S01 N1 C8 N2 -154.3(3) . . . . ?
O3 S01 C5 C4 -22.1(4) . . . . ?
O2 S01 C5 C4 108.9(3) . . . . ?
N1 S01 C5 C4 -140.1(3) . . . . ?
O3 S01 C5 C6 158.3(3) . . . . ?
O2 S01 C5 C6 -70.7(4) . . . . ?
N1 S01 C5 C6 40.3(4) . . . . ?
C8 N2 C9 C10 -85.9(6) . . . . ?
C4 C5 C6 C7 -0.1(7) . . . . ?
S01 C5 C6 C7 179.5(4) . . . . ?
C5 C6 C7 C2 -0.1(7) . . . . ?
C6 C7 C2 C3 -0.9(7) . . . . ?
C6 C7 C2 C1 161.6(10) . . . . ?
C6 C7 C2 Cl1 -176.1(5) . . . . ?
C6 C5 C4 C3 1.3(7) . . . . ?
S01 C5 C4 C3 -178.3(4) . . . . ?
C5 C4 C3 C2 -2.4(8) . . . . ?
C7 C2 C3 C4 2.2(8) . . . . ?
C1 C2 C3 C4 -163.5(9) . . . . ?
Cl1 C2 C3 C4 176.9(5) . . . . ?
N2 C9 C10 C11 179.6(8) . . . . ?
C9 C10 C11 C12 94(3) . . . . ?

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.049



# start Validation Reply Form
_vrf_PLAT234_SS1_54              
;
PROBLEM: Large Hirshfeld Difference C11      --C12      .       0.32 Ang.  
RESPONSE: this is expected in a disordered solid solution
;
_vrf_PLAT245_SS1_54              
;
PROBLEM: U(iso) H11       Smaller than U(eq) C11       by      0.134 Ang**2
RESPONSE: this is expected in a disordered solid solution
;
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_SS2_30
_database_code_depnum_ccdc_archive 'CCDC 2290033'
loop_
_audit_author_name
_audit_author_address
'Matteo Lusi'
;University of Limerick
Ireland
;
_audit_update_record             
;
2023-08-22 deposited with the CCDC.	2023-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'Chloropropamide Tolbutamide'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11.39 H16.49 Cl0.30 N2 O3 S'
_chemical_formula_weight         272.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   15.5366(7)
_cell_length_b                   9.3050(3)
_cell_length_c                   19.6476(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2840.4(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    125
_cell_measurement_theta_min      2
_cell_measurement_theta_max      40

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    2.577
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4693
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28137
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.501
_diffrn_reflns_theta_max         72.315
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2775
_reflns_number_gt                2211
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1320P)²+1.2494P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0078(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2775
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0862
_refine_ls_wR_factor_ref         0.2777
_refine_ls_wR_factor_gt          0.2662
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_refine_ls_shift/su_max          0.674
_refine_ls_shift/su_mean         0.024

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
Cl1 Cl 0.1784(5) 0.0318(8) 0.90795(18) 0.234(5) Uani 0.304(16) 1 d . . P A 1
C1 C 0.1784(5) 0.0318(8) 0.90795(18) 0.234(5) Uani 0.696(16) 1 d . . P A 2
H1A H 0.1817 0.1190 0.9340 0.351 Uiso 0.696(16) 1 calc R U P A 2
H1B H 0.2326 -0.0174 0.9101 0.351 Uiso 0.696(16) 1 calc R U P A 2
H1C H 0.1341 -0.0287 0.9263 0.351 Uiso 0.696(16) 1 calc R U P A 2
C2 C 0.1557(4) 0.0708(9) 0.8279(3) 0.1350(19) Uani 1 1 d . . . . .
C3 C 0.1407(7) 0.2002(9) 0.8086(4) 0.182(3) Uani 1 1 d . . . . .
H3 H 0.1432 0.2744 0.8402 0.218 Uiso 1 1 calc R U . . .
C4 C 0.1209(6) 0.2311(8) 0.7413(4) 0.178(3) Uani 1 1 d . . . . .
H4 H 0.1030 0.3232 0.7297 0.214 Uiso 1 1 calc R U . . .
C5 C 0.1271(3) 0.1302(5) 0.6926(2) 0.0988(11) Uani 1 1 d . . . . .
C6 C 0.1487(6) -0.0041(6) 0.7129(3) 0.158(3) Uani 1 1 d . . . . .
H6 H 0.1531 -0.0772 0.6808 0.190 Uiso 1 1 calc R U . . .
C7 C 0.1644(7) -0.0344(8) 0.7810(3) 0.186(4) Uani 1 1 d . . . . .
H7 H 0.1808 -0.1264 0.7942 0.223 Uiso 1 1 calc R U . . .
S8 S 0.10474(7) 0.17089(11) 0.60665(6) 0.1003(6) Uani 1 1 d . . . . .
N9 N 0.1931(2) 0.2372(3) 0.57591(19) 0.1000(10) Uani 1 1 d . . . . .
H9 H 0.1927 0.3252 0.5625 0.120 Uiso 1 1 calc R U . . .
C10 C 0.2688(3) 0.1613(4) 0.56988(18) 0.0904(11) Uani 1 1 d . . . . .
N11 N 0.3376(3) 0.2400(4) 0.55685(18) 0.1034(11) Uani 1 1 d . . . . .
H11 H 0.3311 0.3314 0.5529 0.124 Uiso 1 1 calc R U . . .
C12 C 0.4229(4) 0.1818(6) 0.5489(3) 0.1259(17) Uani 1 1 d . . . . .
H12A H 0.4551 0.2415 0.5175 0.151 Uiso 1 1 calc R U . . .
H12B H 0.4189 0.0862 0.5294 0.151 Uiso 1 1 calc R U . . .
C13 C 0.4700(5) 0.1737(7) 0.6151(4) 0.162(3) Uani 1 1 d . . . . .
H13A H 0.4711 0.2690 0.6350 0.194 Uiso 1 1 calc R U . . .
H13B H 0.4376 0.1122 0.6456 0.194 Uiso 1 1 calc R U . . .
C14 C 0.5588(6) 0.1198(10) 0.6117(7) 0.206(4) Uani 1 1 d . . . . .
H14A H 0.5947 0.1892 0.5881 0.247 Uiso 1 1 calc R U . A 2
H14B H 0.5601 0.0307 0.5861 0.247 Uiso 1 1 calc R U . A 2
C15 C 0.5937(8) 0.0947(16) 0.6808(8) 0.200(13) Uani 0.696(16) 1 d . . P A 2
H15A H 0.6366 0.0205 0.6790 0.299 Uiso 0.696(16) 1 calc R U P A 2
H15B H 0.5479 0.0655 0.7106 0.299 Uiso 0.696(16) 1 calc R U P A 2
H15C H 0.6191 0.1817 0.6976 0.299 Uiso 0.696(16) 1 calc R U P A 2
O3 O 0.0457(2) 0.2883(4) 0.6040(2) 0.1336(13) Uani 1 1 d . . . . .
O2 O 0.0849(2) 0.0395(3) 0.57312(16) 0.1148(11) Uani 1 1 d . . . . .
O4 O 0.2703(2) 0.0298(3) 0.57565(17) 0.1087(10) Uani 1 1 d . . . . .
H15 H 0.5937(8) 0.0947(16) 0.6808(8) 0.3(3) Uiso 0.304(16) 1 d . . P A 1


_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
Cl1 C2 1.652(7) . ?
C2 C3 1.284(10) . ?
C2 C7 1.351(9) . ?
C3 C4 1.388(11) . ?
C4 C5 1.344(7) . ?
C5 C6 1.355(7) . ?
C5 S8 1.765(5) . ?
C6 C7 1.389(8) . ?
S8 O2 1.423(3) . ?
S8 O3 1.427(3) . ?
S8 N9 1.622(4) . ?
N9 C10 1.376(5) . ?
C10 O4 1.229(4) . ?
C10 N11 1.321(5) . ?
N11 C12 1.439(7) . ?
C12 C13 1.495(10) . ?
C13 C14 1.470(11) . ?
C14 C15 1.480(14) . ?

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
C3 C2 C7 119.7(6) . . ?
C3 C2 Cl1 121.7(6) . . ?
C7 C2 Cl1 118.0(7) . . ?
C2 C3 C4 121.1(6) . . ?
C5 C4 C3 121.2(7) . . ?
C4 C5 C6 116.9(5) . . ?
C4 C5 S8 121.2(5) . . ?
C6 C5 S8 121.9(3) . . ?
C5 C6 C7 121.0(6) . . ?
C2 C7 C6 119.5(7) . . ?
O2 S8 O3 120.1(2) . . ?
O2 S8 N9 109.8(2) . . ?
O3 S8 N9 103.8(2) . . ?
O2 S8 C5 107.6(2) . . ?
O3 S8 C5 109.0(2) . . ?
N9 S8 C5 105.7(2) . . ?
C10 N9 S8 124.1(3) . . ?
O4 C10 N11 123.6(4) . . ?
O4 C10 N9 121.3(4) . . ?
N11 C10 N9 115.1(3) . . ?
C10 N11 C12 123.9(4) . . ?
N11 C12 C13 112.0(5) . . ?
C14 C13 C12 116.0(8) . . ?
C13 C14 C15 110.8(10) . . ?

_refine_diff_density_max         0.289
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.051

_shelxl_version_number           2014-3



# start Validation Reply Form
_vrf_SHFSU01_SS2_30              
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.20
RESPONSE: The shift is due to the coordinates of the H atom of the terminal methyl group. 
;
_vrf_PLAT080_SS2_30              
;
PROBLEM: Maximum Shift/Error ............................       0.67 Why ? 
RESPONSE: The group is likely rotating and the electron density is expected lower than 1.
;
_vrf_PLAT242_SS2_30              
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         C2 Check 
RESPONSE: The atom is attached to either one of two disordered substituents.
;
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_SS3_39
_database_code_depnum_ccdc_archive 'CCDC 2290038'
loop_
_audit_author_name
_audit_author_address
'Matteo Lusi'
;University of Limerick
Ireland
;
_audit_update_record             
;
2023-08-22 deposited with the CCDC.	2023-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'Toluensulfonamide Chlorobenzylsulfonamide'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6.60 H7.81 Cl0.40 N O2 S'
_chemical_formula_weight         179.30

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   9.7280(14)
_cell_length_b                   9.9056(15)
_cell_length_c                   17.743(3)
_cell_angle_alpha                86.808(4)
_cell_angle_beta                 76.707(4)
_cell_angle_gamma                75.775(4)
_cell_volume                     1612.9(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    412
_cell_measurement_theta_min      2
_cell_measurement_theta_max      20

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_F_000             745
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.479
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7024
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31048
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.428
_diffrn_reflns_theta_max         25.418
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             11587
_reflns_number_gt                8681
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.968
_reflns_Friedel_fraction_max     0.958
_reflns_Friedel_fraction_full    0.962

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1138P)²+1.2654P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3639 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.020(18)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         11587
_refine_ls_number_parameters     809
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1950
_refine_ls_wR_factor_gt          0.1680
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.927
_refine_ls_shift/su_mean         0.020

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
Cl1A Cl -0.5191(8) 1.1223(5) 0.1551(4) 0.101(3) Uani 0.46(2) 1 d . . P A 1
C1A C -0.5191(8) 1.1223(5) 0.1551(4) 0.101(3) Uani 0.54(2) 1 d . . P A 2
H1A1 H -0.4304 1.1429 0.1605 0.151 Uiso 0.54(2) 1 calc R U P A 2
H1A2 H -0.5951 1.1568 0.1995 0.151 Uiso 0.54(2) 1 calc R U P A 2
H1A3 H -0.5456 1.1661 0.1092 0.151 Uiso 0.54(2) 1 calc R U P A 2
C2A C -0.4951(10) 0.9519(9) 0.1486(6) 0.050(2) Uani 1 1 d . . . . .
C3A C -0.4940(13) 0.8683(12) 0.2134(7) 0.074(3) Uani 1 1 d . . . . .
H3A H -0.5106 0.9083 0.2619 0.089 Uiso 1 1 calc R U . . .
C4A C -0.4681(12) 0.7247(10) 0.2065(6) 0.062(3) Uani 1 1 d . . . . .
H4A H -0.4652 0.6679 0.2500 0.074 Uiso 1 1 calc R U . . .
C5A C -0.4472(8) 0.6679(8) 0.1351(4) 0.0349(17) Uani 1 1 d . . . . .
C6A C -0.4454(12) 0.7475(10) 0.0712(6) 0.058(2) Uani 1 1 d . . . . .
H6A H -0.4280 0.7076 0.0227 0.069 Uiso 1 1 calc R U . . .
C7A C -0.4706(12) 0.8933(11) 0.0793(7) 0.066(3) Uani 1 1 d . . . . .
H7A H -0.4700 0.9495 0.0355 0.079 Uiso 1 1 calc R U . . .
S8A S -0.42864(19) 0.48658(19) 0.12674(11) 0.0317(5) Uani 1 1 d . . . . .
O9A O -0.3740(6) 0.4195(6) 0.1911(3) 0.0423(13) Uani 1 1 d . . . . .
O10A O -0.5643(6) 0.4644(6) 0.1172(3) 0.0451(14) Uani 1 1 d . . . . .
N11A N -0.3109(7) 0.4335(7) 0.0486(4) 0.0432(16) Uani 1 1 d . . . . .
H11A H -0.2308 0.3741 0.0508 0.052 Uiso 1 1 calc R U . . .
H11B H -0.3276 0.4644 0.0046 0.052 Uiso 1 1 calc R U . . .
Cl1B Cl 0.0043(7) 1.1377(5) 0.1455(3) 0.100(3) Uani 0.55(2) 1 d . . P B 1
C1B C 0.0043(7) 1.1377(5) 0.1455(3) 0.100(3) Uani 0.45(2) 1 d . . P B 2
H1B1 H -0.0444 1.1725 0.1965 0.151 Uiso 0.45(2) 1 calc R U P B 2
H1B2 H -0.0495 1.1849 0.1087 0.151 Uiso 0.45(2) 1 calc R U P B 2
H1B3 H 0.1004 1.1538 0.1329 0.151 Uiso 0.45(2) 1 calc R U P B 2
C1 C 0.0158(12) 0.9647(11) 0.1424(6) 0.058(3) Uani 1 1 d . . . . .
C2B C 0.1308(14) 0.8782(13) 0.1696(7) 0.083(4) Uani 1 1 d . . . . .
H2B H 0.1973 0.9127 0.1882 0.099 Uiso 1 1 calc R U . . .
C3B C 0.1382(13) 0.7364(12) 0.1667(7) 0.075(3) Uani 1 1 d . . . . .
H3B H 0.2106 0.6743 0.1858 0.090 Uiso 1 1 calc R U . . .
C4B C 0.0440(9) 0.6842(10) 0.1369(5) 0.0411(19) Uani 1 1 d . . . . .
C5B C -0.0699(12) 0.7788(11) 0.1118(6) 0.065(3) Uani 1 1 d . . . . .
H5B H -0.1382 0.7469 0.0933 0.078 Uiso 1 1 calc R U . . .
C6B C -0.0790(16) 0.9190(12) 0.1152(7) 0.083(4) Uani 1 1 d . . . . .
H6B H -0.1532 0.9823 0.0980 0.099 Uiso 1 1 calc R U . . .
S7B S 0.0608(2) 0.5020(2) 0.12961(12) 0.0354(5) Uani 1 1 d . . . . .
O8B O 0.1188(6) 0.4353(6) 0.1933(3) 0.0483(15) Uani 1 1 d . . . . .
O9B O -0.0763(6) 0.4817(7) 0.1225(4) 0.0496(15) Uani 1 1 d . . . . .
N10B N 0.1758(7) 0.4482(7) 0.0508(4) 0.0418(15) Uani 1 1 d . . . . .
H10A H 0.1485 0.4150 0.0145 0.050 Uiso 1 1 calc R U . . .
H10B H 0.2649 0.4525 0.0448 0.050 Uiso 1 1 calc R U . . .
Cl1C Cl 0.2222(11) -0.2345(8) 0.3953(6) 0.116(5) Uani 0.32(2) 1 d . . P C 1
C1C C 0.2222(11) -0.2345(8) 0.3953(6) 0.116(5) Uani 0.68(2) 1 d . . P C 2
H1C1 H 0.1720 -0.2561 0.3586 0.174 Uiso 0.68(2) 1 calc R U P C 2
H1C2 H 0.1761 -0.2582 0.4465 0.174 Uiso 0.68(2) 1 calc R U P C 2
H1C3 H 0.3216 -0.2869 0.3831 0.174 Uiso 0.68(2) 1 calc R U P C 2
C2C C 0.2169(12) -0.0715(11) 0.3917(6) 0.060(3) Uani 1 1 d . . . . .
C3C C 0.1226(13) 0.0195(12) 0.3572(7) 0.069(3) Uani 1 1 d . . . . .
H3C H 0.0576 -0.0136 0.3364 0.083 Uiso 1 1 calc R U . . .
C4C C 0.1188(12) 0.1611(10) 0.3514(6) 0.060(3) Uani 1 1 d . . . . .
H4C H 0.0537 0.2201 0.3261 0.071 Uiso 1 1 calc R U . . .
C5C C 0.2106(9) 0.2136(9) 0.3831(5) 0.0398(19) Uani 1 1 d . . . . .
C6C C 0.3098(13) 0.1203(12) 0.4174(6) 0.069(3) Uani 1 1 d . . . . .
H6C H 0.3770 0.1521 0.4369 0.083 Uiso 1 1 calc R U . . .
C7C C 0.3097(16) -0.0202(13) 0.4229(7) 0.087(4) Uani 1 1 d . . . . .
H7C H 0.3740 -0.0804 0.4482 0.105 Uiso 1 1 calc R U . . .
S8C S 0.1962(2) 0.3955(2) 0.38211(11) 0.0379(6) Uani 1 1 d . . . . .
O9C O 0.2455(7) 0.4263(7) 0.4480(3) 0.0533(16) Uani 1 1 d . . . . .
O10C O 0.0509(6) 0.4601(6) 0.3767(3) 0.0458(14) Uani 1 1 d . . . . .
N11C N 0.3040(8) 0.4334(9) 0.3062(4) 0.0516(19) Uani 1 1 d . . . . .
H11C H 0.2697 0.4851 0.2710 0.062 Uiso 1 1 calc R U . . .
H11D H 0.3964 0.4022 0.3004 0.062 Uiso 1 1 calc R U . . .
Cl1D Cl 0.7474(10) -0.2155(7) 0.3872(5) 0.112(4) Uani 0.37(2) 1 d . . P D 1
C1D C 0.7474(10) -0.2155(7) 0.3872(5) 0.112(4) Uani 0.63(2) 1 d . . P D 2
H1D1 H 0.8182 -0.2589 0.4163 0.168 Uiso 0.63(2) 1 calc R U P D 2
H1D2 H 0.7784 -0.2511 0.3352 0.168 Uiso 0.63(2) 1 calc R U P D 2
H1D3 H 0.6553 -0.2352 0.4110 0.168 Uiso 0.63(2) 1 calc R U P D 2
C2D C 0.7308(12) -0.0484(10) 0.3854(6) 0.059(3) Uani 1 1 d . . . . .
C3D C 0.7268(14) 0.0251(12) 0.4500(7) 0.074(3) Uani 1 1 d . . . . .
H3D H 0.7351 -0.0237 0.4957 0.089 Uiso 1 1 calc R U . . .
C4D C 0.7112(12) 0.1664(12) 0.4502(6) 0.066(3) Uani 1 1 d . . . . .
H4D H 0.7041 0.2126 0.4957 0.079 Uiso 1 1 calc R U . . .
C5D C 0.7061(9) 0.2387(8) 0.3821(5) 0.0374(18) Uani 1 1 d . . . . .
C6D C 0.7080(14) 0.1702(10) 0.3167(6) 0.069(3) Uani 1 1 d . . . . .
H6D H 0.6991 0.2192 0.2711 0.082 Uiso 1 1 calc R U . . .
C7D C 0.7234(15) 0.0276(11) 0.3192(7) 0.078(3) Uani 1 1 d . . . . .
H7D H 0.7289 -0.0184 0.2739 0.094 Uiso 1 1 calc R U . . .
S8D S 0.68703(18) 0.42105(19) 0.37988(10) 0.0309(5) Uani 1 1 d . . . . .
O9D O 0.7262(6) 0.4577(6) 0.4480(3) 0.0422(13) Uani 1 1 d . . . . .
O10D O 0.5441(6) 0.4830(6) 0.3690(3) 0.0430(13) Uani 1 1 d . . . . .
N11D N 0.8000(7) 0.4591(7) 0.3068(4) 0.0392(15) Uani 1 1 d . . . . .
H11E H 0.7692 0.5090 0.2700 0.047 Uiso 1 1 calc R U . . .
H11F H 0.8919 0.4297 0.3039 0.047 Uiso 1 1 calc R U . . .
Cl1E Cl 1.0414(9) -0.1157(6) 0.6558(4) 0.102(4) Uani 0.41(2) 1 d . . P E 1
C1E C 1.0414(9) -0.1157(6) 0.6558(4) 0.102(4) Uani 0.59(2) 1 d . . P E 2
H1E1 H 1.0441 -0.1602 0.6086 0.152 Uiso 0.59(2) 1 calc R U P E 2
H1E2 H 0.9777 -0.1500 0.6980 0.152 Uiso 0.59(2) 1 calc R U P E 2
H1E3 H 1.1375 -0.1358 0.6655 0.152 Uiso 0.59(2) 1 calc R U P E 2
C2E C 0.9808(10) 0.0547(10) 0.6479(6) 0.053(2) Uani 1 1 d . . . . .
C3E C 0.9379(14) 0.1400(11) 0.7135(7) 0.075(3) Uani 1 1 d . . . . .
H3E H 0.9408 0.0995 0.7619 0.091 Uiso 1 1 calc R U . . .
C4E C 0.8916(12) 0.2823(10) 0.7083(6) 0.061(3) Uani 1 1 d . . . . .
H4E H 0.8649 0.3385 0.7521 0.074 Uiso 1 1 calc R U . . .
C5E C 0.8861(8) 0.3392(9) 0.6357(4) 0.0356(18) Uani 1 1 d . . . . .
C6E C 0.9247(12) 0.2584(10) 0.5713(6) 0.058(2) Uani 1 1 d . . . . .
H6E H 0.9211 0.2981 0.5228 0.070 Uiso 1 1 calc R U . . .
C7E C 0.9697(12) 0.1145(11) 0.5797(7) 0.067(3) Uani 1 1 d . . . . .
H7E H 0.9927 0.0583 0.5361 0.081 Uiso 1 1 calc R U . . .
S8E S 0.81226(19) 0.51990(19) 0.62841(11) 0.0327(5) Uani 1 1 d . . . . .
O9E O 0.8329(6) 0.5866(6) 0.6931(3) 0.0440(14) Uani 1 1 d . . . . .
O10E O 0.6655(6) 0.5399(6) 0.6199(3) 0.0438(14) Uani 1 1 d . . . . .
N11E N 0.9044(7) 0.5727(7) 0.5503(4) 0.0432(16) Uani 1 1 d . . . . .
H11G H 0.9549 0.6319 0.5527 0.052 Uiso 1 1 calc R U . . .
H11H H 0.9032 0.5419 0.5062 0.052 Uiso 1 1 calc R U . . .
Cl1F Cl 1.5640(6) -0.1277(5) 0.6450(3) 0.092(3) Uani 0.55(2) 1 d . . P F 1
C1F C 1.5640(6) -0.1277(5) 0.6450(3) 0.092(3) Uani 0.45(2) 1 d . . P F 2
H1F1 H 1.6631 -0.1450 0.6497 0.138 Uiso 0.45(2) 1 calc R U P F 2
H1F2 H 1.5605 -0.1694 0.5981 0.138 Uiso 0.45(2) 1 calc R U P F 2
H1F3 H 1.5084 -0.1671 0.6886 0.138 Uiso 0.45(2) 1 calc R U P F 2
C2F C 1.4940(11) 0.0444(11) 0.6423(6) 0.056(2) Uani 1 1 d . . . . .
C3F C 1.5579(14) 0.1333(12) 0.6691(8) 0.083(4) Uani 1 1 d . . . . .
H3F H 1.6405 0.0997 0.6888 0.099 Uiso 1 1 calc R U . . .
C4F C 1.4985(11) 0.2744(11) 0.6664(6) 0.064(3) Uani 1 1 d . . . . .
H4F H 1.5408 0.3348 0.6864 0.076 Uiso 1 1 calc R U . . .
C5F C 1.3817(8) 0.3288(9) 0.6362(4) 0.0371(18) Uani 1 1 d . . . . .
C6F C 1.3135(12) 0.2338(11) 0.6107(6) 0.067(3) Uani 1 1 d . . . . .
H6F H 1.2301 0.2675 0.5916 0.080 Uiso 1 1 calc R U . . .
C7F C 1.3705(15) 0.0905(12) 0.6141(7) 0.079(3) Uani 1 1 d . . . . .
H7F H 1.3261 0.0279 0.5977 0.094 Uiso 1 1 calc R U . . .
S8F S 1.3099(2) 0.5086(2) 0.62819(12) 0.0351(5) Uani 1 1 d . . . . .
O9F O 1.3364(6) 0.5743(6) 0.6912(3) 0.0473(14) Uani 1 1 d . . . . .
O10F O 1.1619(6) 0.5309(6) 0.6209(4) 0.0480(15) Uani 1 1 d . . . . .
N11F N 1.4007(7) 0.5595(7) 0.5494(4) 0.0424(15) Uani 1 1 d . . . . .
H11I H 1.4534 0.6170 0.5509 0.051 Uiso 1 1 calc R U . . .
H11J H 1.3967 0.5294 0.5056 0.051 Uiso 1 1 calc R U . . .
Cl1G Cl 0.6122(12) 1.2326(7) 0.8972(6) 0.109(5) Uani 0.27(2) 1 d . . P G 1
C1G C 0.6122(12) 1.2326(7) 0.8972(6) 0.109(5) Uani 0.73(2) 1 d . . P G 2
H1G1 H 0.5554 1.2564 0.8586 0.164 Uiso 0.73(2) 1 calc R U P G 2
H1G2 H 0.6851 1.2853 0.8885 0.164 Uiso 0.73(2) 1 calc R U P G 2
H1G3 H 0.5499 1.2538 0.9476 0.164 Uiso 0.73(2) 1 calc R U P G 2
C2G C 0.6892(14) 1.0696(11) 0.8918(6) 0.065(3) Uani 1 1 d . . . . .
C3G C 0.8085(15) 1.0170(13) 0.9221(7) 0.079(3) Uani 1 1 d . . . . .
H3G H 0.8454 1.0764 0.9465 0.095 Uiso 1 1 calc R U . . .
C4G C 0.8749(12) 0.8768(12) 0.9170(6) 0.065(3) Uani 1 1 d . . . . .
H4G H 0.9567 0.8436 0.9374 0.078 Uiso 1 1 calc R U . . .
C5G C 0.8225(9) 0.7835(9) 0.8819(5) 0.0416(19) Uani 1 1 d . . . . .
C6G C 0.7014(12) 0.8388(10) 0.8510(6) 0.065(3) Uani 1 1 d . . . . .
H6G H 0.6640 0.7804 0.8263 0.078 Uiso 1 1 calc R U . . .
C7G C 0.6354(14) 0.9807(11) 0.8567(7) 0.072(3) Uani 1 1 d . . . . .
H7G H 0.5537 1.0155 0.8363 0.086 Uiso 1 1 calc R U . . .
S8G S 0.8943(2) 0.6014(2) 0.88077(11) 0.0376(5) Uani 1 1 d . . . . .
O9G O 0.9550(7) 0.5668(7) 0.9475(3) 0.0550(16) Uani 1 1 d . . . . .
O10G O 0.7827(6) 0.5371(6) 0.8725(4) 0.0472(14) Uani 1 1 d . . . . .
N11G N 1.0235(7) 0.5621(8) 0.8064(4) 0.0471(17) Uani 1 1 d . . . . .
H11K H 1.0163 0.5105 0.7708 0.057 Uiso 1 1 calc R U . . .
H11L H 1.1006 0.5924 0.8018 0.057 Uiso 1 1 calc R U . . .
Cl1H Cl 1.1389(13) 1.2294(8) 0.8828(7) 0.119(6) Uani 0.23(2) 1 d . . P H 1
C1H C 1.1389(13) 1.2294(8) 0.8828(7) 0.119(6) Uani 0.77(2) 1 d . . P H 2
H1H1 H 1.0997 1.2639 0.9347 0.179 Uiso 0.77(2) 1 calc R U P H 2
H1H2 H 1.0631 1.2491 0.8545 0.179 Uiso 0.77(2) 1 calc R U P H 2
H1H3 H 1.2145 1.2741 0.8579 0.179 Uiso 0.77(2) 1 calc R U P H 2
C2H C 1.2045(14) 1.0647(11) 0.8847(7) 0.069(3) Uani 1 1 d . . . . .
C3H C 1.2399(14) 0.9933(13) 0.9484(7) 0.086(4) Uani 1 1 d . . . . .
H3H H 1.2264 1.0429 0.9935 0.103 Uiso 1 1 calc R U . . .
C4H C 1.2946(13) 0.8516(12) 0.9488(6) 0.076(3) Uani 1 1 d . . . . .
H4H H 1.3133 0.8068 0.9941 0.091 Uiso 1 1 calc R U . . .
C5H C 1.3216(9) 0.7763(10) 0.8818(5) 0.0422(19) Uani 1 1 d . . . . .
C6H C 1.2866(12) 0.8407(10) 0.8160(6) 0.061(3) Uani 1 1 d . . . . .
H6H H 1.2984 0.7893 0.7717 0.073 Uiso 1 1 calc R U . . .
C7H C 1.2338(14) 0.9828(12) 0.8167(7) 0.079(3) Uani 1 1 d . . . . .
H7H H 1.2165 1.0273 0.7711 0.094 Uiso 1 1 calc R U . . .
S8H S 1.39187(19) 0.5948(2) 0.88101(11) 0.0365(5) Uani 1 1 d . . . . .
O9H O 1.4517(6) 0.5586(7) 0.9479(3) 0.0508(15) Uani 1 1 d . . . . .
O10H O 1.2794(6) 0.5323(7) 0.8721(4) 0.0525(16) Uani 1 1 d . . . . .
N11H N 1.5208(7) 0.5552(8) 0.8069(4) 0.0452(16) Uani 1 1 d . . . . .
H11M H 1.5131 0.5043 0.7711 0.054 Uiso 1 1 calc R U . . .
H11N H 1.5984 0.5845 0.8025 0.054 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1A C2A 1.653(10) . ?
C2A C7A 1.335(14) . ?
C2A C3A 1.379(15) . ?
C3A C4A 1.390(14) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.367(12) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.343(12) . ?
C5A S8A 1.771(8) . ?
C6A C7A 1.414(13) . ?
C6A H6A 0.9300 . ?
C7A H7A 0.9300 . ?
S8A O9A 1.431(5) . ?
S8A O10A 1.438(5) . ?
S8A N11A 1.601(7) . ?
N11A H11A 0.8600 . ?
N11A H11B 0.8600 . ?
Cl1B C1 1.693(11) . ?
C1 C6B 1.313(16) . ?
C1 C2B 1.395(17) . ?
C2B C3B 1.391(16) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.369(13) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.405(13) . ?
C4B S7B 1.781(9) . ?
C5B C6B 1.374(15) . ?
C5B H5B 0.9300 . ?
C6B H6B 0.9300 . ?
S7B O9B 1.431(6) . ?
S7B O8B 1.434(5) . ?
S7B N10B 1.600(7) . ?
N10B H10A 0.8600 . ?
N10B H10B 0.8600 . ?
Cl1C C2C 1.601(13) . ?
C2C C3C 1.349(15) . ?
C2C C7C 1.366(16) . ?
C3C C4C 1.392(15) . ?
C3C H3C 0.9300 . ?
C4C C5C 1.370(12) . ?
C4C H4C 0.9300 . ?
C5C C6C 1.387(13) . ?
C5C S8C 1.773(9) . ?
C6C C7C 1.390(16) . ?
C6C H6C 0.9300 . ?
C7C H7C 0.9300 . ?
S8C O10C 1.423(6) . ?
S8C O9C 1.436(6) . ?
S8C N11C 1.594(7) . ?
N11C H11C 0.8600 . ?
N11C H11D 0.8600 . ?
Cl1D C2D 1.622(11) . ?
C2D C7D 1.366(15) . ?
C2D C3D 1.380(15) . ?
C3D C4D 1.370(15) . ?
C3D H3D 0.9300 . ?
C4D C5D 1.374(12) . ?
C4D H4D 0.9300 . ?
C5D C6D 1.371(12) . ?
C5D S8D 1.769(8) . ?
C6D C7D 1.382(14) . ?
C6D H6D 0.9300 . ?
C7D H7D 0.9300 . ?
S8D O10D 1.428(5) . ?
S8D O9D 1.438(5) . ?
S8D N11D 1.590(6) . ?
N11D H11E 0.8600 . ?
N11D H11F 0.8600 . ?
Cl1E C2E 1.655(11) . ?
C2E C7E 1.333(14) . ?
C2E C3E 1.398(15) . ?
C3E C4E 1.375(14) . ?
C3E H3E 0.9300 . ?
C4E C5E 1.383(12) . ?
C4E H4E 0.9300 . ?
C5E C6E 1.358(12) . ?
C5E S8E 1.767(8) . ?
C6E C7E 1.395(13) . ?
C6E H6E 0.9300 . ?
C7E H7E 0.9300 . ?
S8E O9E 1.431(5) . ?
S8E O10E 1.434(5) . ?
S8E N11E 1.605(7) . ?
N11E H11G 0.8600 . ?
N11E H11H 0.8600 . ?
Cl1F C2F 1.675(11) . ?
C2F C3F 1.356(16) . ?
C2F C7F 1.373(16) . ?
C3F C4F 1.377(15) . ?
C3F H3F 0.9300 . ?
C4F C5F 1.348(12) . ?
C4F H4F 0.9300 . ?
C5F C6F 1.422(13) . ?
C5F S8F 1.757(9) . ?
C6F C7F 1.395(15) . ?
C6F H6F 0.9300 . ?
C7F H7F 0.9300 . ?
S8F O9F 1.428(5) . ?
S8F O10F 1.437(5) . ?
S8F N11F 1.600(7) . ?
N11F H11I 0.8600 . ?
N11F H11J 0.8600 . ?
Cl1G C2G 1.603(13) . ?
C2G C3G 1.366(17) . ?
C2G C7G 1.370(15) . ?
C3G C4G 1.378(16) . ?
C3G H3G 0.9300 . ?
C4G C5G 1.394(13) . ?
C4G H4G 0.9300 . ?
C5G C6G 1.391(12) . ?
C5G S8G 1.767(9) . ?
C6G C7G 1.393(14) . ?
C6G H6G 0.9300 . ?
C7G H7G 0.9300 . ?
S8G O10G 1.425(6) . ?
S8G O9G 1.429(6) . ?
S8G N11G 1.589(7) . ?
N11G H11K 0.8600 . ?
N11G H11L 0.8600 . ?
Cl1H C2H 1.601(13) . ?
C2H C3H 1.366(16) . ?
C2H C7H 1.425(16) . ?
C3H C4H 1.373(16) . ?
C3H H3H 0.9300 . ?
C4H C5H 1.378(12) . ?
C4H H4H 0.9300 . ?
C5H C6H 1.371(12) . ?
C5H S8H 1.758(10) . ?
C6H C7H 1.374(14) . ?
C6H H6H 0.9300 . ?
C7H H7H 0.9300 . ?
S8H O10H 1.424(6) . ?
S8H O9H 1.429(6) . ?
S8H N11H 1.585(7) . ?
N11H H11M 0.8600 . ?
N11H H11N 0.8600 . ?

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
C7A C2A C3A 119.3(9) . . ?
C7A C2A Cl1A 119.6(8) . . ?
C3A C2A Cl1A 120.9(8) . . ?
C2A C3A C4A 120.2(10) . . ?
C2A C3A H3A 119.9 . . ?
C4A C3A H3A 119.9 . . ?
C5A C4A C3A 119.1(9) . . ?
C5A C4A H4A 120.4 . . ?
C3A C4A H4A 120.4 . . ?
C6A C5A C4A 121.3(8) . . ?
C6A C5A S8A 119.2(7) . . ?
C4A C5A S8A 119.4(7) . . ?
C5A C6A C7A 118.7(9) . . ?
C5A C6A H6A 120.7 . . ?
C7A C6A H6A 120.6 . . ?
C2A C7A C6A 121.2(9) . . ?
C2A C7A H7A 119.4 . . ?
C6A C7A H7A 119.4 . . ?
O9A S8A O10A 117.1(3) . . ?
O9A S8A N11A 108.6(4) . . ?
O10A S8A N11A 106.5(4) . . ?
O9A S8A C5A 107.9(4) . . ?
O10A S8A C5A 108.6(4) . . ?
N11A S8A C5A 107.9(4) . . ?
S8A N11A H11A 120.0 . . ?
S8A N11A H11B 120.0 . . ?
H11A N11A H11B 120.0 . . ?
C6B C1 C2B 123.9(11) . . ?
C6B C1 Cl1B 120.3(9) . . ?
C2B C1 Cl1B 115.8(9) . . ?
C3B C2B C1 114.9(10) . . ?
C3B C2B H2B 122.5 . . ?
C1 C2B H2B 122.5 . . ?
C4B C3B C2B 123.1(11) . . ?
C4B C3B H3B 118.5 . . ?
C2B C3B H3B 118.4 . . ?
C3B C4B C5B 118.2(10) . . ?
C3B C4B S7B 122.3(8) . . ?
C5B C4B S7B 119.5(7) . . ?
C6B C5B C4B 119.0(10) . . ?
C6B C5B H5B 120.5 . . ?
C4B C5B H5B 120.5 . . ?
C1 C6B C5B 120.8(11) . . ?
C1 C6B H6B 119.6 . . ?
C5B C6B H6B 119.6 . . ?
O9B S7B O8B 117.4(3) . . ?
O9B S7B N10B 107.1(4) . . ?
O8B S7B N10B 108.4(4) . . ?
O9B S7B C4B 108.1(4) . . ?
O8B S7B C4B 107.8(4) . . ?
N10B S7B C4B 107.7(4) . . ?
S7B N10B H10A 120.0 . . ?
S7B N10B H10B 120.0 . . ?
H10A N10B H10B 120.0 . . ?
C3C C2C C7C 117.7(10) . . ?
C3C C2C Cl1C 121.5(10) . . ?
C7C C2C Cl1C 120.7(10) . . ?
C2C C3C C4C 122.5(10) . . ?
C2C C3C H3C 118.8 . . ?
C4C C3C H3C 118.7 . . ?
C5C C4C C3C 120.1(9) . . ?
C5C C4C H4C 119.9 . . ?
C3C C4C H4C 119.9 . . ?
C4C C5C C6C 117.7(9) . . ?
C4C C5C S8C 120.0(7) . . ?
C6C C5C S8C 122.3(7) . . ?
C5C C6C C7C 120.7(10) . . ?
C5C C6C H6C 119.7 . . ?
C7C C6C H6C 119.7 . . ?
C2C C7C C6C 121.2(10) . . ?
C2C C7C H7C 119.4 . . ?
C6C C7C H7C 119.4 . . ?
O10C S8C O9C 118.5(4) . . ?
O10C S8C N11C 108.3(4) . . ?
O9C S8C N11C 107.8(4) . . ?
O10C S8C C5C 106.2(4) . . ?
O9C S8C C5C 106.9(4) . . ?
N11C S8C C5C 108.8(4) . . ?
S8C N11C H11C 120.0 . . ?
S8C N11C H11D 120.0 . . ?
H11C N11C H11D 120.0 . . ?
C7D C2D C3D 115.9(9) . . ?
C7D C2D Cl1D 121.9(9) . . ?
C3D C2D Cl1D 122.1(9) . . ?
C4D C3D C2D 123.3(9) . . ?
C4D C3D H3D 118.4 . . ?
C2D C3D H3D 118.4 . . ?
C3D C4D C5D 118.9(10) . . ?
C3D C4D H4D 120.6 . . ?
C5D C4D H4D 120.5 . . ?
C6D C5D C4D 119.7(9) . . ?
C6D C5D S8D 119.9(7) . . ?
C4D C5D S8D 120.3(7) . . ?
C5D C6D C7D 119.3(9) . . ?
C5D C6D H6D 120.4 . . ?
C7D C6D H6D 120.3 . . ?
C2D C7D C6D 122.7(10) . . ?
C2D C7D H7D 118.7 . . ?
C6D C7D H7D 118.6 . . ?
O10D S8D O9D 118.3(3) . . ?
O10D S8D N11D 107.8(3) . . ?
O9D S8D N11D 107.6(3) . . ?
O10D S8D C5D 106.8(4) . . ?
O9D S8D C5D 107.3(4) . . ?
N11D S8D C5D 108.9(4) . . ?
S8D N11D H11E 120.0 . . ?
S8D N11D H11F 120.0 . . ?
H11E N11D H11F 120.0 . . ?
C7E C2E C3E 118.1(9) . . ?
C7E C2E Cl1E 121.5(8) . . ?
C3E C2E Cl1E 120.4(8) . . ?
C4E C3E C2E 121.7(9) . . ?
C4E C3E H3E 119.2 . . ?
C2E C3E H3E 119.2 . . ?
C3E C4E C5E 117.8(9) . . ?
C3E C4E H4E 121.1 . . ?
C5E C4E H4E 121.1 . . ?
C6E C5E C4E 121.7(8) . . ?
C6E C5E S8E 119.4(6) . . ?
C4E C5E S8E 118.7(7) . . ?
C5E C6E C7E 118.3(9) . . ?
C5E C6E H6E 120.8 . . ?
C7E C6E H6E 120.8 . . ?
C2E C7E C6E 122.3(9) . . ?
C2E C7E H7E 118.8 . . ?
C6E C7E H7E 118.8 . . ?
O9E S8E O10E 116.8(3) . . ?
O9E S8E N11E 108.7(4) . . ?
O10E S8E N11E 107.8(4) . . ?
O9E S8E C5E 107.8(4) . . ?
O10E S8E C5E 108.2(3) . . ?
N11E S8E C5E 107.1(4) . . ?
S8E N11E H11G 120.0 . . ?
S8E N11E H11H 120.0 . . ?
H11G N11E H11H 120.0 . . ?
C3F C2F C7F 122.1(10) . . ?
C3F C2F Cl1F 119.9(9) . . ?
C7F C2F Cl1F 118.1(9) . . ?
C2F C3F C4F 118.9(10) . . ?
C2F C3F H3F 120.6 . . ?
C4F C3F H3F 120.5 . . ?
C5F C4F C3F 122.9(10) . . ?
C5F C4F H4F 118.5 . . ?
C3F C4F H4F 118.5 . . ?
C4F C5F C6F 117.3(9) . . ?
C4F C5F S8F 123.4(7) . . ?
C6F C5F S8F 119.3(6) . . ?
C7F C6F C5F 120.6(9) . . ?
C7F C6F H6F 119.7 . . ?
C5F C6F H6F 119.7 . . ?
C2F C7F C6F 118.1(10) . . ?
C2F C7F H7F 120.9 . . ?
C6F C7F H7F 120.9 . . ?
O9F S8F O10F 117.8(3) . . ?
O9F S8F N11F 108.1(4) . . ?
O10F S8F N11F 107.6(4) . . ?
O9F S8F C5F 107.2(4) . . ?
O10F S8F C5F 108.5(4) . . ?
N11F S8F C5F 107.2(4) . . ?
S8F N11F H11I 120.0 . . ?
S8F N11F H11J 120.0 . . ?
H11I N11F H11J 120.0 . . ?
C3G C2G C7G 119.0(11) . . ?
C3G C2G Cl1G 120.9(9) . . ?
C7G C2G Cl1G 120.0(11) . . ?
C2G C3G C4G 120.7(10) . . ?
C2G C3G H3G 119.7 . . ?
C4G C3G H3G 119.7 . . ?
C3G C4G C5G 121.7(10) . . ?
C3G C4G H4G 119.1 . . ?
C5G C4G H4G 119.1 . . ?
C6G C5G C4G 116.9(9) . . ?
C6G C5G S8G 119.6(7) . . ?
C4G C5G S8G 123.4(7) . . ?
C5G C6G C7G 120.8(10) . . ?
C5G C6G H6G 119.6 . . ?
C7G C6G H6G 119.6 . . ?
C2G C7G C6G 120.9(11) . . ?
C2G C7G H7G 119.6 . . ?
C6G C7G H7G 119.6 . . ?
O10G S8G O9G 117.9(4) . . ?
O10G S8G N11G 107.4(4) . . ?
O9G S8G N11G 107.6(4) . . ?
O10G S8G C5G 107.6(4) . . ?
O9G S8G C5G 107.4(4) . . ?
N11G S8G C5G 108.6(4) . . ?
S8G N11G H11K 120.0 . . ?
S8G N11G H11L 120.0 . . ?
H11K N11G H11L 120.0 . . ?
C3H C2H C7H 115.4(10) . . ?
C3H C2H Cl1H 124.2(10) . . ?
C7H C2H Cl1H 120.4(10) . . ?
C2H C3H C4H 123.1(10) . . ?
C2H C3H H3H 118.5 . . ?
C4H C3H H3H 118.5 . . ?
C3H C4H C5H 119.7(10) . . ?
C3H C4H H4H 120.2 . . ?
C5H C4H H4H 120.2 . . ?
C6H C5H C4H 120.4(9) . . ?
C6H C5H S8H 119.1(7) . . ?
C4H C5H S8H 120.5(7) . . ?
C5H C6H C7H 118.7(9) . . ?
C5H C6H H6H 120.6 . . ?
C7H C6H H6H 120.7 . . ?
C6H C7H C2H 122.6(10) . . ?
C6H C7H H7H 118.7 . . ?
C2H C7H H7H 118.7 . . ?
O10H S8H O9H 117.8(4) . . ?
O10H S8H N11H 107.3(4) . . ?
O9H S8H N11H 107.7(4) . . ?
O10H S8H C5H 107.2(4) . . ?
O9H S8H C5H 108.0(4) . . ?
N11H S8H C5H 108.5(4) . . ?
S8H N11H H11M 120.0 . . ?
S8H N11H H11N 120.0 . . ?
H11M N11H H11N 120.0 . . ?

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
C7A C2A C3A C4A -0.3(16) . . . . ?
Cl1A C2A C3A C4A -177.5(9) . . . . ?
C2A C3A C4A C5A -1.4(16) . . . . ?
C3A C4A C5A C6A 2.6(15) . . . . ?
C3A C4A C5A S8A -175.0(8) . . . . ?
C4A C5A C6A C7A -2.0(15) . . . . ?
S8A C5A C6A C7A 175.6(8) . . . . ?
C3A C2A C7A C6A 0.9(16) . . . . ?
Cl1A C2A C7A C6A 178.1(9) . . . . ?
C5A C6A C7A C2A 0.3(16) . . . . ?
C6A C5A S8A O9A 156.3(7) . . . . ?
C4A C5A S8A O9A -26.0(8) . . . . ?
C6A C5A S8A O10A -75.9(8) . . . . ?
C4A C5A S8A O10A 101.7(8) . . . . ?
C6A C5A S8A N11A 39.2(8) . . . . ?
C4A C5A S8A N11A -143.2(7) . . . . ?
C6B C1 C2B C3B -0.6(18) . . . . ?
Cl1B C1 C2B C3B 179.9(9) . . . . ?
C1 C2B C3B C4B 2.4(17) . . . . ?
C2B C3B C4B C5B -3.4(17) . . . . ?
C2B C3B C4B S7B 177.0(9) . . . . ?
C3B C4B C5B C6B 2.6(16) . . . . ?
S7B C4B C5B C6B -177.8(9) . . . . ?
C2B C1 C6B C5B 0(2) . . . . ?
Cl1B C1 C6B C5B 179.4(10) . . . . ?
C4B C5B C6B C1 -1.0(19) . . . . ?
C3B C4B S7B O9B 160.2(8) . . . . ?
C5B C4B S7B O9B -19.4(9) . . . . ?
C3B C4B S7B O8B 32.4(9) . . . . ?
C5B C4B S7B O8B -147.2(8) . . . . ?
C3B C4B S7B N10B -84.4(9) . . . . ?
C5B C4B S7B N10B 96.1(8) . . . . ?
C7C C2C C3C C4C 1.1(18) . . . . ?
Cl1C C2C C3C C4C -178.2(10) . . . . ?
C2C C3C C4C C5C -1.6(17) . . . . ?
C3C C4C C5C C6C 2.7(15) . . . . ?
C3C C4C C5C S8C -175.3(8) . . . . ?
C4C C5C C6C C7C -3.4(16) . . . . ?
S8C C5C C6C C7C 174.5(9) . . . . ?
C3C C2C C7C C6C -1.8(19) . . . . ?
Cl1C C2C C7C C6C 177.5(11) . . . . ?
C5C C6C C7C C2C 3(2) . . . . ?
C4C C5C S8C O10C 24.1(9) . . . . ?
C6C C5C S8C O10C -153.8(8) . . . . ?
C4C C5C S8C O9C 151.5(8) . . . . ?
C6C C5C S8C O9C -26.4(9) . . . . ?
C4C C5C S8C N11C -92.3(8) . . . . ?
C6C C5C S8C N11C 89.8(9) . . . . ?
C7D C2D C3D C4D 2.3(19) . . . . ?
Cl1D C2D C3D C4D -179.2(10) . . . . ?
C2D C3D C4D C5D -3.2(18) . . . . ?
C3D C4D C5D C6D 3.9(16) . . . . ?
C3D C4D C5D S8D -179.7(8) . . . . ?
C4D C5D C6D C7D -3.7(17) . . . . ?
S8D C5D C6D C7D 179.8(9) . . . . ?
C3D C2D C7D C6D -2.0(19) . . . . ?
Cl1D C2D C7D C6D 179.4(11) . . . . ?
C5D C6D C7D C2D 2.8(19) . . . . ?
C6D C5D S8D O10D 66.9(9) . . . . ?
C4D C5D S8D O10D -109.5(8) . . . . ?
C6D C5D S8D O9D -165.3(8) . . . . ?
C4D C5D S8D O9D 18.2(9) . . . . ?
C6D C5D S8D N11D -49.2(9) . . . . ?
C4D C5D S8D N11D 134.3(8) . . . . ?
C7E C2E C3E C4E -2.9(17) . . . . ?
Cl1E C2E C3E C4E 177.9(9) . . . . ?
C2E C3E C4E C5E 1.1(17) . . . . ?
C3E C4E C5E C6E 0.1(15) . . . . ?
C3E C4E C5E S8E 174.6(8) . . . . ?
C4E C5E C6E C7E 0.4(15) . . . . ?
S8E C5E C6E C7E -174.0(8) . . . . ?
C3E C2E C7E C6E 3.5(17) . . . . ?
Cl1E C2E C7E C6E -177.2(9) . . . . ?
C5E C6E C7E C2E -2.4(17) . . . . ?
C6E C5E S8E O9E -158.3(7) . . . . ?
C4E C5E S8E O9E 27.1(8) . . . . ?
C6E C5E S8E O10E 74.5(8) . . . . ?
C4E C5E S8E O10E -100.1(8) . . . . ?
C6E C5E S8E N11E -41.4(8) . . . . ?
C4E C5E S8E N11E 144.0(7) . . . . ?
C7F C2F C3F C4F -1.2(18) . . . . ?
Cl1F C2F C3F C4F -179.9(9) . . . . ?
C2F C3F C4F C5F -2.1(19) . . . . ?
C3F C4F C5F C6F 4.0(16) . . . . ?
C3F C4F C5F S8F -176.9(9) . . . . ?
C4F C5F C6F C7F -2.8(15) . . . . ?
S8F C5F C6F C7F 178.1(9) . . . . ?
C3F C2F C7F C6F 2.3(18) . . . . ?
Cl1F C2F C7F C6F -179.0(9) . . . . ?
C5F C6F C7F C2F -0.3(17) . . . . ?
C4F C5F S8F O9F -31.1(9) . . . . ?
C6F C5F S8F O9F 148.0(7) . . . . ?
C4F C5F S8F O10F -159.3(8) . . . . ?
C6F C5F S8F O10F 19.8(8) . . . . ?
C4F C5F S8F N11F 84.7(9) . . . . ?
C6F C5F S8F N11F -96.2(8) . . . . ?
C7G C2G C3G C4G 0.6(18) . . . . ?
Cl1G C2G C3G C4G -179.6(10) . . . . ?
C2G C3G C4G C5G -0.8(18) . . . . ?
C3G C4G C5G C6G 1.1(16) . . . . ?
C3G C4G C5G S8G -174.6(9) . . . . ?
C4G C5G C6G C7G -1.1(16) . . . . ?
S8G C5G C6G C7G 174.8(9) . . . . ?
C3G C2G C7G C6G -0.6(18) . . . . ?
Cl1G C2G C7G C6G 179.6(10) . . . . ?
C5G C6G C7G C2G 0.9(18) . . . . ?
C6G C5G S8G O10G -20.7(9) . . . . ?
C4G C5G S8G O10G 154.9(8) . . . . ?
C6G C5G S8G O9G -148.5(8) . . . . ?
C4G C5G S8G O9G 27.1(9) . . . . ?
C6G C5G S8G N11G 95.4(8) . . . . ?
C4G C5G S8G N11G -89.0(9) . . . . ?
C7H C2H C3H C4H -3(2) . . . . ?
Cl1H C2H C3H C4H 179.3(12) . . . . ?
C2H C3H C4H C5H 3(2) . . . . ?
C3H C4H C5H C6H -3.7(17) . . . . ?
C3H C4H C5H S8H 179.9(10) . . . . ?
C4H C5H C6H C7H 4.5(16) . . . . ?
S8H C5H C6H C7H -179.0(9) . . . . ?
C5H C6H C7H C2H -4.4(18) . . . . ?
C3H C2H C7H C6H 3.4(19) . . . . ?
Cl1H C2H C7H C6H -178.3(11) . . . . ?
C6H C5H S8H O10H -66.0(9) . . . . ?
C4H C5H S8H O10H 110.5(9) . . . . ?
C6H C5H S8H O9H 166.1(8) . . . . ?
C4H C5H S8H O9H -17.4(10) . . . . ?
C6H C5H S8H N11H 49.6(9) . . . . ?
C4H C5H S8H N11H -133.9(9) . . . . ?

_refine_diff_density_max         0.675
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.100

_shelxl_version_number           2014-3



# start Validation Reply Form
_vrf_SHFSU01_SS3_39              
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.20
RESPONSE: the shift is caused by the retaton of the methyl hydrogen atoms
;
_vrf_PLAT080_SS3_39              
;
PROBLEM: Maximum Shift/Error ............................       0.93 Why ? 
RESPONSE: the electron density on the hydrogen atoms is lower than 1 preventing a stable refinment
;
_vrf_PLAT340_SS3_39              
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01554 Ang.  
RESPONSE: this is due to the occupancy disorder and the use of the EXYZ command
;
_vrf_PLAT919_SS3_39              
;
PROBLEM: Reflection # Likely Affected by the Beamstop ...          1 Check 
RESPONSE: the reflection was outside the beamstop
;
_exptl_crystal_recrystallization_method 'Vapour deposition'
_chemical_properties_physical    metastable
####################################################################### 
# 
# 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_SS2_40
_database_code_depnum_ccdc_archive 'CCDC 2290035'
loop_
_audit_author_name
_audit_author_address
'Matteo Lusi'
;University of Limerick
Ireland
;
_audit_update_record             
;
2023-08-22 deposited with the CCDC.	2023-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'Chloropropamide Tolbutamide'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11.18 H15.96 Cl0.41 N2 O3 S'
_chemical_formula_weight         272.97

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   15.2433(8)
_cell_length_b                   9.3138(5)
_cell_length_c                   19.5618(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2777.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    452
_cell_measurement_theta_min      2
_cell_measurement_theta_max      40

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.312
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            63177
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.474
_diffrn_reflns_theta_max         25.475
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2567
_reflns_number_gt                1664
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1441P)²+3.2372P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.054(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2567
_refine_ls_number_parameters     168
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1460
_refine_ls_R_factor_gt           0.1048
_refine_ls_wR_factor_ref         0.3244
_refine_ls_wR_factor_gt          0.2836
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          4.886
_refine_ls_shift/su_mean         0.132

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
Cl1 Cl 0.1808(4) 0.0240(7) 0.91370(19) 0.182(4) Uani 0.420(15) 1 d . . P A 1
C1 C 0.1808(4) 0.0240(7) 0.91370(19) 0.182(4) Uani 0.580(15) 1 d . . P A 2
H1A H 0.2432 0.0205 0.9204 0.273 Uiso 0.580(15) 1 calc R U P A 2
H1B H 0.1558 -0.0680 0.9243 0.273 Uiso 0.580(15) 1 calc R U P A 2
H1C H 0.1559 0.0956 0.9432 0.273 Uiso 0.580(15) 1 calc R U P A 2
C2 C 0.1589(6) 0.0659(11) 0.8315(3) 0.118(2) Uani 1 1 d . . . . .
C3 C 0.1416(8) 0.1993(12) 0.8124(5) 0.154(4) Uani 1 1 d . . . . .
H3 H 0.1419 0.2719 0.8450 0.184 Uiso 1 1 calc R U . . .
C4 C 0.1231(8) 0.2340(9) 0.7443(5) 0.153(4) Uani 1 1 d . . . . .
H4 H 0.1085 0.3277 0.7324 0.183 Uiso 1 1 calc R U . . .
C5 C 0.1263(4) 0.1320(6) 0.6963(3) 0.0884(17) Uani 1 1 d . . . . .
C6 C 0.1425(7) -0.0049(8) 0.7163(4) 0.137(3) Uani 1 1 d . . . . .
H6 H 0.1436 -0.0779 0.6838 0.164 Uiso 1 1 calc R U . . .
C7 C 0.1571(8) -0.0371(10) 0.7837(4) 0.163(4) Uani 1 1 d . . . . .
H7 H 0.1660 -0.1321 0.7964 0.196 Uiso 1 1 calc R U . . .
S8 S 0.10348(11) 0.17175(16) 0.61018(9) 0.0928(8) Uani 1 1 d . . . . .
N9 N 0.1941(4) 0.2379(5) 0.5792(3) 0.0919(15) Uani 1 1 d . . . . .
H9 H 0.1940 0.3258 0.5658 0.110 Uiso 1 1 calc R U . . .
C10 C 0.2716(4) 0.1601(6) 0.5733(3) 0.0809(16) Uani 1 1 d . . . . .
N11 N 0.3415(4) 0.2389(5) 0.5599(3) 0.0961(17) Uani 1 1 d . . . . .
H11 H 0.3351 0.3303 0.5562 0.115 Uiso 1 1 calc R U . . .
C12 C 0.4287(6) 0.1787(8) 0.5512(5) 0.120(3) Uani 1 1 d . . . . .
H12A H 0.4610 0.2359 0.5183 0.144 Uiso 1 1 calc R U . . .
H12B H 0.4238 0.0820 0.5332 0.144 Uiso 1 1 calc R U . . .
C13 C 0.4789(8) 0.1750(11) 0.6184(7) 0.179(5) Uani 1 1 d . . . . .
H13A H 0.4833 0.2716 0.6366 0.215 Uiso 1 1 calc R U . . .
H13B H 0.4470 0.1168 0.6512 0.215 Uiso 1 1 calc R U . . .
C14 C 0.5660(10) 0.1166(16) 0.6095(10) 0.218(7) Uani 1 1 d . . . . .
H14A H 0.6045 0.1836 0.5862 0.261 Uiso 1 1 calc R U . A 2
H14B H 0.5649 0.0264 0.5847 0.261 Uiso 1 1 calc R U . A 2
C15 C 0.5921(11) 0.096(2) 0.6820(11) 0.157(13) Uani 0.580(15) 1 d . U P A 2
H15A H 0.5447 0.1245 0.7113 0.235 Uiso 0.580(15) 1 calc R U P A 2
H15B H 0.6428 0.1535 0.6917 0.235 Uiso 0.580(15) 1 calc R U P A 2
H15C H 0.6056 -0.0034 0.6898 0.235 Uiso 0.580(15) 1 calc R U P A 2
O3 O 0.0436(3) 0.2895(5) 0.6077(3) 0.1238(18) Uani 1 1 d . . . . .
O2 O 0.0818(3) 0.0423(5) 0.5757(2) 0.1069(15) Uani 1 1 d . . . . .
O4 O 0.2713(3) 0.0307(4) 0.5798(2) 0.1020(15) Uani 1 1 d . . . . .
H15 H 0.5921(11) 0.096(2) 0.6820(11) 0.3(3) Uiso 0.420(15) 1 d . . P A 1


_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
Cl1 C2 1.688(9) . ?
C1 C2 1.688(9) . ?
C2 C3 1.324(12) . ?
C2 C7 1.341(11) . ?
C3 C4 1.399(13) . ?
C4 C5 1.336(9) . ?
C5 C6 1.356(10) . ?
C5 S8 1.760(6) . ?
C6 C7 1.370(10) . ?
S8 O2 1.420(4) . ?
S8 O3 1.427(5) . ?
S8 N9 1.629(6) . ?
N9 C10 1.390(8) . ?
C10 O4 1.212(6) . ?
C10 N11 1.320(7) . ?
N11 C12 1.453(9) . ?
C12 C13 1.521(14) . ?
C13 C14 1.445(16) . ?
C14 C15 1.49(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C2 C7 118.0(8) . . ?
C3 C2 C1 121.7(7) . . ?
C7 C2 C1 120.2(8) . . ?
C3 C2 Cl1 121.7(7) . . ?
C7 C2 Cl1 120.2(8) . . ?
C2 C3 C4 121.7(7) . . ?
C5 C4 C3 119.8(8) . . ?
C4 C5 C6 118.3(7) . . ?
C4 C5 S8 121.0(6) . . ?
C6 C5 S8 120.6(5) . . ?
C5 C6 C7 120.8(8) . . ?
C2 C7 C6 121.2(9) . . ?
O2 S8 O3 119.2(3) . . ?
O2 S8 N9 110.0(3) . . ?
O3 S8 N9 103.8(3) . . ?
O2 S8 C5 108.8(3) . . ?
O3 S8 C5 108.7(3) . . ?
N9 S8 C5 105.5(3) . . ?
C10 N9 S8 123.7(4) . . ?
O4 C10 N11 125.2(6) . . ?
O4 C10 N9 120.5(6) . . ?
N11 C10 N9 114.4(5) . . ?
C10 N11 C12 123.2(5) . . ?
N11 C12 C13 111.6(7) . . ?
C14 C13 C12 111.5(12) . . ?
C13 C14 C15 100.3(14) . . ?

_refine_diff_density_max         0.688
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.164



# start Validation Reply Form
_vrf_SHFSU01_SS2_40              
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.20
RESPONSE: That is referred to the position of a H atom on a terminal methyl group.
;
_vrf_PLAT080_SS2_40              
;
PROBLEM: Maximum Shift/Error ............................       4.89 Why ? 
RESPONSE: The position of the H atom cannot be defined by X-ray
;
_vrf_PLAT242_SS2_40              
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         C2 Check 
RESPONSE: The atom is attached to a disordered group
;
_vrf_PLAT340_SS2_40              
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01338 Ang.  
RESPONSE: This is expected in case of disordered structures
;
_vrf_PLAT919_SS2_40              
;
PROBLEM: Reflection # Likely Affected by the Beamstop ...          1 Check 
RESPONSE: The reflection is not affected by the beam stopper
;
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_SS4_60
_database_code_depnum_ccdc_archive 'CCDC 2290039'
loop_
_audit_author_name
_audit_author_address
'Matteo Lusi'
;University of Limerick
Ireland
;
_audit_update_record             
;
2023-08-22 deposited with the CCDC.	2023-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'Toluensulfonamide Chlorobenzylsulfonamide'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6.39 H7.16 Cl0.61 N O2 S'
_chemical_formula_weight         183.71

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.6126(6)
_cell_length_b                   16.3343(17)
_cell_length_c                   7.6345(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.933(3)
_cell_angle_gamma                90
_cell_volume                     823.54(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    126
_cell_measurement_theta_min      2
_cell_measurement_theta_max      20

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.539
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7030
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23369
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_av_R_equivalents  0.1449
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.494
_diffrn_reflns_theta_max         25.453
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1517
_reflns_number_gt                869
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1009P)²+0.2012P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.046(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1517
_refine_ls_number_parameters     103
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1357
_refine_ls_R_factor_gt           0.0634
_refine_ls_wR_factor_ref         0.2057
_refine_ls_wR_factor_gt          0.1485
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          1.485
_refine_ls_shift/su_mean         0.014

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
Cl1 Cl 0.2379(5) 0.59739(17) 0.1671(4) 0.1098(18) Uani 0.611(12) 1 d . . P A 2
S1 S 0.73030(18) 0.28180(9) 0.35360(17) 0.0501(6) Uani 1 1 d . . . . .
O1 O 0.9256(5) 0.3037(3) 0.4277(5) 0.0670(12) Uani 1 1 d . . . . .
N1 N 0.7668(6) 0.2354(3) 0.1748(6) 0.0572(13) Uani 1 1 d . . . . .
H1A H 0.8880 0.2284 0.1419 0.069 Uiso 1 1 calc R U . . .
H1B H 0.6654 0.2174 0.1111 0.069 Uiso 1 1 calc R U . . .
C1 C 0.2379(5) 0.59739(17) 0.1671(4) 0.1098(18) Uani 0.389(12) 1 d . . P A 1
H1C H 0.3243 0.6437 0.1508 0.165 Uiso 0.389(12) 1 calc R U P A 1
H1D H 0.1504 0.6085 0.2607 0.165 Uiso 0.389(12) 1 calc R U P A 1
H1E H 0.1577 0.5873 0.0609 0.165 Uiso 0.389(12) 1 calc R U P A 1
O2 O 0.6014(5) 0.2304(2) 0.4507(5) 0.0646(12) Uani 1 1 d . . . . .
C2 C 0.3826(10) 0.5133(4) 0.2182(7) 0.0649(16) Uani 1 1 d . . . . .
C3 C 0.5823(11) 0.5182(4) 0.2749(8) 0.0715(18) Uani 1 1 d . . . . .
H3 H 0.6457 0.5689 0.2839 0.086 Uiso 1 1 calc R U . . .
C4 C 0.6894(8) 0.4482(4) 0.3183(7) 0.0615(16) Uani 1 1 d . . . . .
H4 H 0.8250 0.4517 0.3564 0.074 Uiso 1 1 calc R U . . .
C5 C 0.5948(7) 0.3725(3) 0.3052(6) 0.0459(13) Uani 1 1 d . . . . .
C6 C 0.3936(7) 0.3670(4) 0.2490(7) 0.0585(15) Uani 1 1 d . . . . .
H6 H 0.3292 0.3164 0.2408 0.070 Uiso 1 1 calc R U . . .
C7 C 0.2899(8) 0.4379(4) 0.2053(8) 0.0640(16) Uani 1 1 d . . . . .
H7 H 0.1546 0.4348 0.1663 0.077 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.708(6) . ?
S1 O1 1.429(3) . ?
S1 O2 1.431(4) . ?
S1 N1 1.590(4) . ?
S1 C5 1.761(5) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C2 C3 1.371(9) . ?
C2 C7 1.377(8) . ?
C3 C4 1.375(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(7) . ?
C6 C7 1.378(8) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?

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
O1 S1 O2 119.5(2) . . ?
O1 S1 N1 106.6(2) . . ?
O2 S1 N1 106.6(2) . . ?
O1 S1 C5 108.2(2) . . ?
O2 S1 C5 107.0(2) . . ?
N1 S1 C5 108.6(2) . . ?
S1 N1 H1A 120.0 . . ?
S1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C3 C2 C7 119.5(5) . . ?
C3 C2 Cl1 123.0(5) . . ?
C7 C2 Cl1 117.4(5) . . ?
C2 C3 C4 120.2(6) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 119.9(5) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.3(5) . . ?
C6 C5 S1 118.9(4) . . ?
C4 C5 S1 120.8(4) . . ?
C7 C6 C5 118.7(5) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C2 C7 C6 121.4(5) . . ?
C2 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?

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
C7 C2 C3 C4 0.0(9) . . . . ?
Cl1 C2 C3 C4 178.3(4) . . . . ?
C2 C3 C4 C5 -0.2(9) . . . . ?
C3 C4 C5 C6 -0.1(8) . . . . ?
C3 C4 C5 S1 178.1(4) . . . . ?
O1 S1 C5 C6 -173.3(4) . . . . ?
O2 S1 C5 C6 -43.4(5) . . . . ?
N1 S1 C5 C6 71.4(4) . . . . ?
O1 S1 C5 C4 8.5(5) . . . . ?
O2 S1 C5 C4 138.5(4) . . . . ?
N1 S1 C5 C4 -106.8(4) . . . . ?
C4 C5 C6 C7 0.4(8) . . . . ?
S1 C5 C6 C7 -177.7(4) . . . . ?
C3 C2 C7 C6 0.3(9) . . . . ?
Cl1 C2 C7 C6 -178.1(4) . . . . ?
C5 C6 C7 C2 -0.6(8) . . . . ?

_refine_diff_density_max         0.431
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.115

_shelxl_version_number           2014-3



# start Validation Reply Form
_vrf_SHFSU01_SS4_60              
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.20
RESPONSE: the shift is caused by the retaton of the methyl hydrogen atoms
;
_vrf_PLAT080_SS4_60              
;
PROBLEM: Maximum Shift/Error ............................       1.49 Why ? 
RESPONSE: the electron density on the hydrogen atoms is lower than 1 preventing a stable refinment
;
_vrf_PLAT919_SS4_60              
;
PROBLEM: Reflection # Likely Affected by the Beamstop ...          1 Check 
RESPONSE: the reflection was outside the beamstop
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# 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_SS2_46
_database_code_depnum_ccdc_archive 'CCDC 2290036'
loop_
_audit_author_name
_audit_author_address
'Matteo Lusi'
;University of Limerick
Ireland
;
_audit_update_record             
;
2023-08-22 deposited with the CCDC.	2023-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'Chloropropamide Tolbutamide'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11.07 H15.66 Cl0.47 N2 O3 S'
_chemical_formula_weight         273.35

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   15.1745(11)
_cell_length_b                   9.3155(5)
_cell_length_c                   19.5240(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2759.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    543
_cell_measurement_theta_min      2
_cell_measurement_theta_max      40

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.325
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6732
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33581
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.481
_diffrn_reflns_theta_max         25.378
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2530
_reflns_number_gt                1562
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1449P)²+2.4113P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.039(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2530
_refine_ls_number_parameters     168
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1423
_refine_ls_R_factor_gt           0.0937
_refine_ls_wR_factor_ref         0.3051
_refine_ls_wR_factor_gt          0.2588
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          4.541
_refine_ls_shift/su_mean         0.112

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
Cl1 Cl 0.1820(4) 0.0226(6) 0.91517(16) 0.170(3) Uani 0.469(14) 1 d . . P A 1
C1 C 0.1820(4) 0.0226(6) 0.91517(16) 0.170(3) Uani 0.531(14) 1 d . . P A 2
H1A H 0.1283 0.0219 0.9412 0.256 Uiso 0.531(14) 1 calc R U P A 2
H1B H 0.2216 0.0924 0.9341 0.256 Uiso 0.531(14) 1 calc R U P A 2
H1C H 0.2088 -0.0706 0.9170 0.256 Uiso 0.531(14) 1 calc R U P A 2
C2 C 0.1595(5) 0.0654(10) 0.8327(3) 0.112(2) Uani 1 1 d . . . . .
C3 C 0.1432(7) 0.1993(10) 0.8134(5) 0.148(3) Uani 1 1 d . . . . .
H3 H 0.1432 0.2717 0.8462 0.177 Uiso 1 1 calc R U . . .
C4 C 0.1261(7) 0.2348(8) 0.7448(4) 0.140(3) Uani 1 1 d . . . . .
H4 H 0.1147 0.3295 0.7326 0.169 Uiso 1 1 calc R U . . .
C5 C 0.1260(4) 0.1319(6) 0.6972(3) 0.0835(15) Uani 1 1 d . . . . .
C6 C 0.1408(6) -0.0047(8) 0.7173(3) 0.130(3) Uani 1 1 d . . . . .
H6 H 0.1410 -0.0777 0.6848 0.156 Uiso 1 1 calc R U . . .
C7 C 0.1555(7) -0.0378(9) 0.7846(4) 0.153(4) Uani 1 1 d . . . . .
H7 H 0.1628 -0.1333 0.7973 0.184 Uiso 1 1 calc R U . . .
S8 S 0.10312(11) 0.17254(15) 0.61095(8) 0.0893(7) Uani 1 1 d . . . . .
N9 N 0.1943(3) 0.2382(4) 0.5800(2) 0.0872(14) Uani 1 1 d . . . . .
H9 H 0.1943 0.3262 0.5666 0.105 Uiso 1 1 calc R U . . .
C10 C 0.2721(4) 0.1599(5) 0.5741(2) 0.0788(15) Uani 1 1 d . . . . .
N11 N 0.3426(4) 0.2389(5) 0.5605(2) 0.0937(16) Uani 1 1 d . . . . .
H11 H 0.3362 0.3303 0.5567 0.112 Uiso 1 1 calc R U . . .
C12 C 0.4297(5) 0.1786(8) 0.5516(4) 0.116(2) Uani 1 1 d . . . . .
H12A H 0.4618 0.2348 0.5180 0.139 Uiso 1 1 calc R U . . .
H12B H 0.4245 0.0814 0.5343 0.139 Uiso 1 1 calc R U . . .
C13 C 0.4808(7) 0.1766(10) 0.6177(7) 0.177(5) Uani 1 1 d . . . . .
H13A H 0.4853 0.2738 0.6351 0.213 Uiso 1 1 calc R U . . .
H13B H 0.4486 0.1202 0.6512 0.213 Uiso 1 1 calc R U . . .
C14 C 0.5683(9) 0.1176(14) 0.6103(9) 0.217(7) Uani 1 1 d . . . . .
H14A H 0.6080 0.1843 0.5878 0.260 Uiso 1 1 calc R U . A 2
H14B H 0.5679 0.0273 0.5856 0.260 Uiso 1 1 calc R U . A 2
C15 C 0.5914(11) 0.097(2) 0.6853(10) 0.152(11) Uani 0.531(14) 1 d . U P A 2
H15A H 0.5419 0.1241 0.7132 0.228 Uiso 0.531(14) 1 calc R U P A 2
H15B H 0.6411 0.1563 0.6967 0.228 Uiso 0.531(14) 1 calc R U P A 2
H15C H 0.6057 -0.0017 0.6935 0.228 Uiso 0.531(14) 1 calc R U P A 2
O3 O 0.0434(3) 0.2904(5) 0.6090(3) 0.1189(16) Uani 1 1 d . . . . .
O2 O 0.0814(3) 0.0431(4) 0.5763(2) 0.1030(14) Uani 1 1 d . . . . .
O4 O 0.2718(3) 0.0306(4) 0.5808(2) 0.0985(14) Uani 1 1 d . . . . .
H15 H 0.5914(11) 0.097(2) 0.6853(10) 0.3(2) Uiso 0.469(14) 1 d . . P A 1


_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
Cl1 C2 1.693(8) . ?
C2 C3 1.326(11) . ?
C2 C7 1.346(10) . ?
C3 C4 1.403(12) . ?
C4 C5 1.335(8) . ?
C5 C6 1.350(9) . ?
C5 S8 1.762(6) . ?
C6 C7 1.367(9) . ?
S8 O2 1.421(4) . ?
S8 O3 1.424(4) . ?
S8 N9 1.629(5) . ?
N9 C10 1.394(7) . ?
C10 O4 1.211(6) . ?
C10 N11 1.325(7) . ?
N11 C12 1.447(8) . ?
C12 C13 1.505(13) . ?
C13 C14 1.445(15) . ?
C14 C15 1.518(19) . ?

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
C3 C2 C7 117.7(7) . . ?
C3 C2 Cl1 122.0(6) . . ?
C7 C2 Cl1 120.3(7) . . ?
C2 C3 C4 121.9(7) . . ?
C5 C4 C3 119.6(7) . . ?
C4 C5 C6 118.3(6) . . ?
C4 C5 S8 120.7(5) . . ?
C6 C5 S8 120.9(4) . . ?
C5 C6 C7 121.2(7) . . ?
C2 C7 C6 121.1(8) . . ?
O2 S8 O3 119.6(3) . . ?
O2 S8 N9 109.8(3) . . ?
O3 S8 N9 103.9(3) . . ?
O2 S8 C5 108.6(3) . . ?
O3 S8 C5 108.5(3) . . ?
N9 S8 C5 105.5(3) . . ?
C10 N9 S8 123.6(3) . . ?
O4 C10 N11 125.2(6) . . ?
O4 C10 N9 120.6(5) . . ?
N11 C10 N9 114.2(4) . . ?
C10 N11 C12 123.1(5) . . ?
N11 C12 C13 111.9(7) . . ?
C14 C13 C12 113.1(11) . . ?
C13 C14 C15 99.4(13) . . ?

_refine_diff_density_max         0.709
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.153

_shelxl_version_number           2014-3



# start Validation Reply Form
_vrf_SHFSU01_SS2_46              
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.20
RESPONSE: The shift is due to the coordinates of the H atom of the terminal methyl group.
;
_vrf_PLAT080_SS2_46              
;
PROBLEM: Maximum Shift/Error ............................       4.54 Why ? 
RESPONSE: The group is likely rotating and the electron density is expected lower than 1.
;
_vrf_PLAT241_SS2_46              
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of        C14 Check 
RESPONSE: depending on the molecule C14 is either a terminal carbon or a bridging one therfore an unusual behaviour is expected 
;
_vrf_PLAT340_SS2_46              
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01225 Ang.  
RESPONSE: This is due to the disorder in the structure
;
_vrf_PLAT919_SS2_46              
;
PROBLEM: Reflection # Likely Affected by the Beamstop ...          1 Check 
RESPONSE: this was checked and the reflection is fully visble
;
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_SS2_34
_database_code_depnum_ccdc_archive 'CCDC 2290034'
loop_
_audit_author_name
_audit_author_address
'Matteo Lusi'
;University of Limerick
Ireland
;
_audit_update_record             
;
2023-08-22 deposited with the CCDC.	2023-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'Chloropropamide Tolbutamide'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11.32 H16.31 Cl0.34 N2 O3 S'
_chemical_formula_weight         272.52

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   15.2556(11)
_cell_length_b                   9.3161(7)
_cell_length_c                   19.5590(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2779.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    523
_cell_measurement_theta_min      2
_cell_measurement_theta_max      40

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.299
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6966
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53341
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_av_R_equivalents  0.0951
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.562
_diffrn_reflns_theta_max         25.367
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2546
_reflns_number_gt                1296
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1681P)²+1.8640P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.022(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2546
_refine_ls_number_parameters     168
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1733
_refine_ls_R_factor_gt           0.1098
_refine_ls_wR_factor_ref         0.3390
_refine_ls_wR_factor_gt          0.2811
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          2.500
_refine_ls_shift/su_mean         0.077

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
Cl1 Cl 0.1804(5) 0.0244(7) 0.9132(2) 0.172(4) Uani 0.345(15) 1 d . . P A 1
C1 C 0.1804(5) 0.0244(7) 0.9132(2) 0.172(4) Uani 0.655(15) 1 d . . P A 2
H1A H 0.1473 0.0853 0.9432 0.258 Uiso 0.655(15) 1 calc R U P A 2
H1B H 0.2419 0.0377 0.9214 0.258 Uiso 0.655(15) 1 calc R U P A 2
H1C H 0.1650 -0.0740 0.9214 0.258 Uiso 0.655(15) 1 calc R U P A 2
C2 C 0.1573(6) 0.0670(11) 0.8311(4) 0.121(3) Uani 1 1 d . . . . .
C3 C 0.1411(9) 0.1983(13) 0.8122(5) 0.160(4) Uani 1 1 d . . . . .
H3 H 0.1414 0.2706 0.8450 0.192 Uiso 1 1 calc R U . . .
C4 C 0.1234(8) 0.2342(9) 0.7443(5) 0.156(4) Uani 1 1 d . . . . .
H4 H 0.1096 0.3282 0.7323 0.187 Uiso 1 1 calc R U . . .
C5 C 0.1265(4) 0.1317(7) 0.6968(3) 0.0906(19) Uani 1 1 d . . . . .
C6 C 0.1422(7) -0.0051(8) 0.7161(4) 0.139(4) Uani 1 1 d . . . . .
H6 H 0.1413 -0.0780 0.6836 0.167 Uiso 1 1 calc R U . . .
C7 C 0.1595(8) -0.0378(10) 0.7834(5) 0.164(4) Uani 1 1 d . . . . .
H7 H 0.1728 -0.1316 0.7959 0.197 Uiso 1 1 calc R U . . .
S8 S 0.10371(13) 0.17161(16) 0.61003(9) 0.0949(8) Uani 1 1 d . . . . .
N9 N 0.1940(4) 0.2380(5) 0.5790(3) 0.0938(17) Uani 1 1 d . . . . .
H9 H 0.1936 0.3257 0.5653 0.113 Uiso 1 1 calc R U . . .
C10 C 0.2721(5) 0.1609(6) 0.5732(3) 0.0823(18) Uani 1 1 d . . . . .
N11 N 0.3411(4) 0.2388(5) 0.5601(3) 0.0985(18) Uani 1 1 d . . . . .
H11 H 0.3352 0.3303 0.5570 0.118 Uiso 1 1 calc R U . . .
C12 C 0.4271(6) 0.1769(8) 0.5504(5) 0.122(3) Uani 1 1 d . . . . .
H12A H 0.4589 0.2319 0.5164 0.146 Uiso 1 1 calc R U . . .
H12B H 0.4212 0.0794 0.5337 0.146 Uiso 1 1 calc R U . . .
C13 C 0.4785(8) 0.1759(11) 0.6167(7) 0.175(5) Uani 1 1 d . . . . .
H13A H 0.4829 0.2737 0.6333 0.210 Uiso 1 1 calc R U . . .
H13B H 0.4457 0.1214 0.6503 0.210 Uiso 1 1 calc R U . . .
C14 C 0.5665(10) 0.1160(15) 0.6122(10) 0.214(6) Uani 1 1 d . . . . .
H14A H 0.6065 0.1813 0.5893 0.256 Uiso 1 1 calc R U . A 2
H14B H 0.5666 0.0244 0.5886 0.256 Uiso 1 1 calc R U . A 2
C15 C 0.5885(12) 0.099(2) 0.6843(10) 0.178(17) Uani 0.655(15) 1 d . U P A 2
H15A H 0.6318 0.1694 0.6969 0.267 Uiso 0.655(15) 1 calc R U P A 2
H15B H 0.6114 0.0048 0.6921 0.267 Uiso 0.655(15) 1 calc R U P A 2
H15C H 0.5368 0.1131 0.7115 0.267 Uiso 0.655(15) 1 calc R U P A 2
O3 O 0.0442(3) 0.2901(5) 0.6082(3) 0.1269(19) Uani 1 1 d . . . . .
O2 O 0.0824(3) 0.0423(5) 0.5755(2) 0.1078(16) Uani 1 1 d . . . . .
O4 O 0.2715(3) 0.0301(4) 0.5797(2) 0.1034(16) Uani 1 1 d . . . . .
H15 H 0.5885(12) 0.099(2) 0.6843(10) 0.3(4) Uiso 0.345(15) 1 d . . P A 1


_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
Cl1 C2 1.691(9) . ?
C2 C3 1.301(12) . ?
C2 C7 1.351(12) . ?
C3 C4 1.396(13) . ?
C4 C5 1.332(9) . ?
C5 C6 1.351(10) . ?
C5 S8 1.772(7) . ?
C6 C7 1.377(11) . ?
S8 O2 1.419(4) . ?
S8 O3 1.430(5) . ?
S8 N9 1.628(6) . ?
N9 C10 1.396(8) . ?
C10 O4 1.225(7) . ?
C10 N11 1.303(8) . ?
N11 C12 1.446(9) . ?
C12 C13 1.515(14) . ?
C13 C14 1.456(16) . ?
C14 C15 1.459(18) . ?

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
C3 C2 C7 119.2(8) . . ?
C3 C2 Cl1 122.0(8) . . ?
C7 C2 Cl1 118.7(8) . . ?
C2 C3 C4 122.1(8) . . ?
C5 C4 C3 119.0(9) . . ?
C4 C5 C6 119.2(8) . . ?
C4 C5 S8 120.7(7) . . ?
C6 C5 S8 120.0(5) . . ?
C5 C6 C7 120.6(8) . . ?
C2 C7 C6 119.7(9) . . ?
O2 S8 O3 119.9(3) . . ?
O2 S8 N9 109.8(3) . . ?
O3 S8 N9 103.6(3) . . ?
O2 S8 C5 108.8(3) . . ?
O3 S8 C5 108.0(3) . . ?
N9 S8 C5 105.7(3) . . ?
C10 N9 S8 123.9(4) . . ?
O4 C10 N11 125.5(7) . . ?
O4 C10 N9 119.8(6) . . ?
N11 C10 N9 114.7(5) . . ?
C10 N11 C12 122.4(6) . . ?
N11 C12 C13 111.2(8) . . ?
C14 C13 C12 115.3(12) . . ?
C13 C14 C15 101.2(14) . . ?

_refine_diff_density_max         0.580
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.164

_shelxl_version_number           2014-3



# start Validation Reply Form
_vrf_SHFSU01_SS2_34              
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.20
RESPONSE: The shift is due to the coordinates of the H atom of the terminal methyl group
;
_vrf_PLAT080_SS2_34              
;
PROBLEM: Maximum Shift/Error ............................       2.50 Why ? 
RESPONSE: The group is likely rotating and the electron density is expected lower than 1
;
_vrf_PLAT340_SS2_34              
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.014 Ang.  
RESPONSE: ...
;
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_SS2_69
_database_code_depnum_ccdc_archive 'CCDC 2290037'
loop_
_audit_author_name
_audit_author_address
'Matteo Lusi'
;University of Limerick
Ireland
;
_audit_update_record             
;
2023-08-22 deposited with the CCDC.	2023-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'Chloropropamide Tolbutamide'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10.61 H14.52 Cl0.70 N2 O3 S'
_chemical_formula_weight         274.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   14.9416(4)
_cell_length_b                   9.3109(3)
_cell_length_c                   19.3930(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2697.95(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    234
_cell_measurement_theta_min      2
_cell_measurement_theta_max      40

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    3.421
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.3407
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8156
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.560
_diffrn_reflns_theta_max         72.136
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             2560
_reflns_number_gt                1832
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1354P)²+0.9311P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2560
_refine_ls_number_parameters     168
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0763
_refine_ls_wR_factor_ref         0.2525
_refine_ls_wR_factor_gt          0.2286
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          2.546
_refine_ls_shift/su_mean         0.085

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
Cl1 Cl 0.18334(19) 0.0177(3) 0.91945(8) 0.1546(14) Uani 0.696(10) 1 d . . P A 1
C1 C 0.18334(19) 0.0177(3) 0.91945(8) 0.1546(14) Uani 0.304(10) 1 d . . P A 2
H1A H 0.1313 0.0357 0.9472 0.232 Uiso 0.304(10) 1 calc R U P A 2
H1B H 0.2325 0.0740 0.9364 0.232 Uiso 0.304(10) 1 calc R U P A 2
H1C H 0.1985 -0.0824 0.9218 0.232 Uiso 0.304(10) 1 calc R U P A 2
C2 C 0.1614(3) 0.0639(6) 0.8357(2) 0.1030(13) Uani 1 1 d . . . . .
C3 C 0.1473(5) 0.2005(7) 0.8180(3) 0.1305(19) Uani 1 1 d . . . . .
H3 H 0.1496 0.2718 0.8515 0.157 Uiso 1 1 calc R U . . .
C4 C 0.1289(4) 0.2376(5) 0.7492(3) 0.1232(17) Uani 1 1 d . . . . .
H4 H 0.1190 0.3330 0.7371 0.148 Uiso 1 1 calc R U . . .
C5 C 0.1258(3) 0.1328(4) 0.70056(19) 0.0831(10) Uani 1 1 d . . . . .
C6 C 0.1374(4) -0.0069(5) 0.7191(2) 0.1109(16) Uani 1 1 d . . . . .
H6 H 0.1332 -0.0789 0.6861 0.133 Uiso 1 1 calc R U . . .
C7 C 0.1555(5) -0.0421(6) 0.7873(2) 0.130(2) Uani 1 1 d . . . . .
H7 H 0.1635 -0.1376 0.8000 0.156 Uiso 1 1 calc R U . . .
S8 S 0.10186(7) 0.17694(11) 0.61434(5) 0.0886(5) Uani 1 1 d . . . . .
N9 N 0.1944(2) 0.2430(3) 0.58343(17) 0.0879(10) Uani 1 1 d . . . . .
H9 H 0.1947 0.3311 0.5702 0.105 Uiso 1 1 calc R U . . .
C10 C 0.2726(3) 0.1645(4) 0.57744(16) 0.0779(10) Uani 1 1 d . . . . .
N11 N 0.3445(2) 0.2420(4) 0.56339(16) 0.0900(10) Uani 1 1 d . . . . .
H11 H 0.3389 0.3336 0.5600 0.108 Uiso 1 1 calc R U . . .
C12 C 0.4325(4) 0.1793(6) 0.5534(3) 0.1151(16) Uani 1 1 d . . . . .
H12A H 0.4640 0.2326 0.5179 0.138 Uiso 1 1 calc R U . . .
H12B H 0.4258 0.0811 0.5375 0.138 Uiso 1 1 calc R U . . .
C13 C 0.4888(5) 0.1804(7) 0.6203(4) 0.169(3) Uani 1 1 d . . . . .
H13A H 0.4970 0.2791 0.6350 0.203 Uiso 1 1 calc R U . . .
H13B H 0.4557 0.1309 0.6562 0.203 Uiso 1 1 calc R U . . .
C14 C 0.5767(6) 0.1131(9) 0.6133(7) 0.213(5) Uani 1 1 d . . . . .
H14A H 0.5712 0.0193 0.5919 0.255 Uiso 1 1 calc R U . A 2
H14B H 0.6158 0.1721 0.5851 0.255 Uiso 1 1 calc R U . A 2
C15 C 0.6104(15) 0.100(2) 0.6795(10) 0.147(12) Uani 0.304(10) 1 d . U P A 2
H15A H 0.6531 0.1756 0.6876 0.220 Uiso 0.304(10) 1 calc R U P A 2
H15B H 0.6390 0.0088 0.6846 0.220 Uiso 0.304(10) 1 calc R U P A 2
H15C H 0.5623 0.1084 0.7121 0.220 Uiso 0.304(10) 1 calc R U P A 2
O3 O 0.0423(2) 0.2956(4) 0.61286(19) 0.1143(11) Uani 1 1 d . . . . .
O2 O 0.0796(2) 0.0482(3) 0.57889(15) 0.1031(10) Uani 1 1 d . . . . .
O4 O 0.2719(2) 0.0333(3) 0.58457(15) 0.0978(9) Uani 1 1 d . . . . .
H15 H 0.6104(15) 0.100(2) 0.6795(10) 0.25(11) Uiso 0.696(10) 1 d . . P A 1


_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
Cl1 C2 1.712(5) . ?
C1 C2 1.712(5) . ?
C2 C3 1.334(8) . ?
C2 C7 1.364(7) . ?
C3 C4 1.405(8) . ?
C4 C5 1.358(6) . ?
C5 C6 1.360(6) . ?
C5 S8 1.758(4) . ?
C6 C7 1.389(6) . ?
S8 O3 1.419(3) . ?
S8 O2 1.421(3) . ?
S8 N9 1.627(4) . ?
N9 C10 1.383(5) . ?
C10 O4 1.230(4) . ?
C10 N11 1.323(5) . ?
N11 C12 1.451(6) . ?
C12 C13 1.547(9) . ?
C13 C14 1.461(10) . ?
C14 C15 1.384(18) . ?

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
C3 C2 C7 120.2(5) . . ?
C3 C2 C1 120.9(4) . . ?
C7 C2 C1 118.9(4) . . ?
C3 C2 Cl1 120.9(4) . . ?
C7 C2 Cl1 118.9(4) . . ?
C2 C3 C4 120.7(4) . . ?
C5 C4 C3 119.3(5) . . ?
C4 C5 C6 119.9(4) . . ?
C4 C5 S8 120.0(4) . . ?
C6 C5 S8 120.1(3) . . ?
C5 C6 C7 120.2(4) . . ?
C2 C7 C6 119.7(5) . . ?
O3 S8 O2 120.0(2) . . ?
O3 S8 N9 103.35(19) . . ?
O2 S8 N9 109.9(2) . . ?
O3 S8 C5 109.2(2) . . ?
O2 S8 C5 108.09(18) . . ?
N9 S8 C5 105.42(18) . . ?
C10 N9 S8 123.3(3) . . ?
O4 C10 N11 124.9(4) . . ?
O4 C10 N9 120.5(4) . . ?
N11 C10 N9 114.6(3) . . ?
C10 N11 C12 123.0(4) . . ?
N11 C12 C13 112.2(4) . . ?
C14 C13 C12 114.0(8) . . ?
C15 C14 C13 106.0(13) . . ?

_refine_diff_density_max         0.335
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.055



# start Validation Reply Form
_vrf_SHFSU01_SS2_69              
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.20
RESPONSE: The shift refers to the position of H atom on the terminal methyl group, which is invisible to X-ray and added for aestetic reasons. 
;
_vrf_PLAT080_SS2_69              
;
PROBLEM: Maximum Shift/Error ............................       2.55 Why ? 
RESPONSE: The shift refers to the position of H atom on the terminal methyl group, which is invisible to X-ray and added for aestetic reasons. 
;
_vrf_PLAT241_SS2_69              
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of        C14 Check 
RESPONSE: this is the disordered carbon in the solid solution
;
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
