# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_7b
_database_code_depnum_ccdc_archive 'CCDC 2328883'
loop_
_audit_author_name
_audit_author_address
'Cosimo Cardellicchio'
;CNR ICCOM
Italy
;
_audit_update_record             
;
2024-01-27 deposited with the CCDC.	2024-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
2-Benzylsulfinyl-1-methyl-1H-benzo[d]imidazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 N2 O S'
_chemical_formula_sum            'C15 H14 N2 O S'
_chemical_formula_weight         270.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   4.7062(4)
_cell_length_b                   23.5001(18)
_cell_length_c                   6.3164(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.6410(10)
_cell_angle_gamma                90
_cell_volume                     665.72(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2581
_cell_measurement_theta_min      3.38
_cell_measurement_theta_max      24.54

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.236
_shelx_estimated_absorpt_T_min   0.871
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS, 2.05'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker SMART-APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.13
_diffrn_reflns_number            5272
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.733
_diffrn_reflns_theta_max         28.697
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3065
_reflns_number_gt                2831
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_max     0.848
_reflns_Friedel_fraction_full    0.983

_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       'SMART 5.6 (Bruker)'
_computing_cell_refinement       'SAINT 5.0 (Bruker)'
_computing_data_reduction        'SAINT 5.0 (Bruker)'
_computing_structure_solution    'SHELXTL-NT 6.1 (Bruker)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0686P)²+0.0053P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_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 1164 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3065
_refine_ls_number_parameters     173
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1142
_refine_ls_wR_factor_gt          0.1116
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3997(9) 0.06973(17) 0.6674(7) 0.0534(9) Uani 1 1 d . . . . .
H1A H 0.330498 0.084211 0.786942 0.064 Uiso 1 1 calc R U . . .
H1B H 0.227558 0.058860 0.544872 0.064 Uiso 1 1 calc R U . . .
S2 S 0.61553(16) 0.12416(3) 0.57769(13) 0.0437(2) Uani 1 1 d . . . . .
O2 O 0.6449(7) 0.10460(12) 0.3621(5) 0.0625(7) Uani 1 1 d . . . . .
C11 C 0.6002(8) 0.01935(14) 0.7459(6) 0.0467(8) Uani 1 1 d . . . . .
C12 C 0.7343(11) 0.00986(19) 0.9688(7) 0.0618(10) Uani 1 1 d . . . . .
H12 H 0.694254 0.034169 1.072463 0.074 Uiso 1 1 calc R U . . .
C13 C 0.9271(12) -0.0351(2) 1.0408(8) 0.0766(13) Uani 1 1 d . . . . .
H13 H 1.014901 -0.040948 1.192264 0.092 Uiso 1 1 calc R U . . .
C14 C 0.9904(12) -0.07115(19) 0.8924(9) 0.0712(12) Uani 1 1 d . . . . .
H14 H 1.121578 -0.101331 0.941770 0.085 Uiso 1 1 calc R U . . .
C15 C 0.8582(11) -0.06246(18) 0.6687(8) 0.0672(12) Uani 1 1 d . . . . .
H15 H 0.901071 -0.086809 0.566398 0.081 Uiso 1 1 calc R U . . .
C16 C 0.6629(9) -0.01798(17) 0.5952(6) 0.0546(9) Uani 1 1 d . . . . .
H16 H 0.572339 -0.012856 0.443715 0.066 Uiso 1 1 calc R U . . .
C21 C 0.3444(7) 0.17946(13) 0.5324(5) 0.0386(7) Uani 1 1 d . . . . .
N22 N 0.1340(6) 0.19254(12) 0.3388(4) 0.0398(6) Uani 1 1 d . . . . .
C22 C 0.0676(9) 0.16470(18) 0.1211(5) 0.0531(9) Uani 1 1 d . . . . .
H22A H 0.221641 0.173524 0.055549 0.080 Uiso 1 1 calc R U . . .
H22B H -0.120523 0.178107 0.026075 0.080 Uiso 1 1 calc R U . . .
H22C H 0.058397 0.124250 0.139341 0.080 Uiso 1 1 calc R U . . .
C23 C -0.0199(7) 0.23817(13) 0.3848(5) 0.0388(6) Uani 1 1 d . . . . .
C24 C -0.2595(8) 0.26913(16) 0.2526(6) 0.0510(8) Uani 1 1 d . . . . .
H24 H -0.344096 0.261051 0.102511 0.061 Uiso 1 1 calc R U . . .
C25 C -0.3649(9) 0.31215(16) 0.3543(7) 0.0586(10) Uani 1 1 d . . . . .
H25 H -0.527343 0.333465 0.271904 0.070 Uiso 1 1 calc R U . . .
C26 C -0.2335(9) 0.32480(16) 0.5797(7) 0.0576(10) Uani 1 1 d . . . . .
H26 H -0.308965 0.354764 0.642629 0.069 Uiso 1 1 calc R U . . .
C27 C 0.0035(9) 0.29415(16) 0.7102(6) 0.0520(8) Uani 1 1 d . . . . .
H27 H 0.088402 0.302683 0.859913 0.062 Uiso 1 1 calc R U . . .
C28 C 0.1118(7) 0.24996(13) 0.6107(5) 0.0399(7) Uani 1 1 d . . . . .
N29 N 0.3455(6) 0.21239(12) 0.6999(4) 0.0430(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C11 1.501(5) . ?
C1 S2 1.827(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
S2 O2 1.483(3) . ?
S2 C21 1.783(3) . ?
C11 C12 1.375(6) . ?
C11 C16 1.391(5) . ?
C12 C13 1.378(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.361(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 N29 1.309(4) . ?
C21 N22 1.355(4) . ?
N22 C23 1.374(4) . ?
N22 C22 1.468(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.388(5) . ?
C23 C28 1.400(4) . ?
C24 C25 1.369(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.402(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.373(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.388(5) . ?
C27 H27 0.9300 . ?
C28 N29 1.390(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C1 S2 107.6(2) . . ?
C11 C1 H1A 110.2 . . ?
S2 C1 H1A 110.2 . . ?
C11 C1 H1B 110.2 . . ?
S2 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
O2 S2 C21 109.88(16) . . ?
O2 S2 C1 106.45(18) . . ?
C21 S2 C1 97.01(15) . . ?
C12 C11 C16 118.1(4) . . ?
C12 C11 C1 120.9(3) . . ?
C16 C11 C1 120.9(3) . . ?
C11 C12 C13 120.9(4) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 120.6(4) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 119.3(4) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C16 120.5(4) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.5(4) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
N29 C21 N22 114.7(3) . . ?
N29 C21 S2 118.3(2) . . ?
N22 C21 S2 127.0(2) . . ?
C21 N22 C23 105.9(2) . . ?
C21 N22 C22 129.3(3) . . ?
C23 N22 C22 124.7(3) . . ?
N22 C22 H22A 109.5 . . ?
N22 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N22 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N22 C23 C24 131.8(3) . . ?
N22 C23 C28 105.7(3) . . ?
C24 C23 C28 122.5(3) . . ?
C25 C24 C23 116.7(3) . . ?
C25 C24 H24 121.7 . . ?
C23 C24 H24 121.7 . . ?
C24 C25 C26 121.5(4) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
C27 C26 C25 121.8(4) . . ?
C27 C26 H26 119.1 . . ?
C25 C26 H26 119.1 . . ?
C26 C27 C28 117.6(4) . . ?
C26 C27 H27 121.2 . . ?
C28 C27 H27 121.2 . . ?
C27 C28 N29 130.2(3) . . ?
C27 C28 C23 120.0(3) . . ?
N29 C28 C23 109.8(3) . . ?
C21 N29 C28 103.9(3) . . ?

_refine_diff_density_max         0.453
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.050



####################################################################### 
# 
# 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_6B
_database_code_depnum_ccdc_archive 'CCDC 2328886'
loop_
_audit_author_name
_audit_author_address
'Cosimo Cardellicchio'
;CNR ICCOM
Italy
;
_audit_update_record             
;
2024-01-27 deposited with the CCDC.	2024-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
(2,3,4,5,6-pentafluorobenzylsulfinyl)-1H-benzo[d]imidazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H7 F5 N2 O S'
_chemical_formula_weight         346.28

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'
F F 0.0171 0.0103 '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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   8.1880(4)
_cell_length_b                   7.0323(4)
_cell_length_c                   12.3527(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.82(3)
_cell_angle_gamma                90
_cell_volume                     693.55(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6450
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      28.38

_exptl_crystal_description       table
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.296
_shelx_estimated_absorpt_T_min   0.847
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS, 2.05'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker SMART-APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.13
_diffrn_reflns_number            5473
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0107
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.691
_diffrn_reflns_theta_max         28.509
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             3134
_reflns_number_gt                3016
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_max     0.821
_reflns_Friedel_fraction_full    0.955

_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       'SMART 5.6 (Bruker)'
_computing_cell_refinement       'SAINT 5.0 (Bruker)'
_computing_data_reduction        'SAINT 5.0 (Bruker)'
_computing_structure_solution    'SHELXTL-NT 6.1 (Bruker)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0676P)²+0.0526P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_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 1255 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.065(19)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3134
_refine_ls_number_parameters     212
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0976
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2386(4) 0.5097(5) 0.4322(2) 0.0635(8) Uani 1 1 d . . . . .
H1A H 0.359733 0.519326 0.451174 0.076 Uiso 1 1 calc R U . . .
H1B H 0.208647 0.378831 0.412099 0.076 Uiso 1 1 calc R U . . .
O2 O -0.0262(2) 0.5170(3) 0.52113(17) 0.0570(5) Uani 1 1 d . . . . .
S2 S 0.15282(7) 0.57998(9) 0.55061(5) 0.04557(17) Uani 1 1 d . . . . .
C11 C 0.1681(3) 0.6389(5) 0.3366(2) 0.0590(7) Uani 1 1 d . . . . .
C12 C 0.2288(4) 0.8206(7) 0.3334(3) 0.0709(10) Uani 1 1 d . . . . .
C13 C 0.1652(6) 0.9453(8) 0.2482(4) 0.1028(18) Uani 1 1 d . . . . .
C14 C 0.0379(7) 0.8828(13) 0.1634(4) 0.125(3) Uani 1 1 d . . . . .
C15 C -0.0262(5) 0.7069(13) 0.1641(3) 0.110(2) Uani 1 1 d . . . . .
C16 C 0.0393(4) 0.5812(9) 0.2507(3) 0.0815(11) Uani 1 1 d . . . . .
F12 F 0.3522(3) 0.8817(4) 0.4161(2) 0.0893(7) Uani 1 1 d . . . . .
F13 F 0.2290(5) 1.1197(6) 0.2473(4) 0.1540(17) Uani 1 1 d . . . . .
F14 F -0.0254(5) 1.0015(9) 0.0798(3) 0.195(3) Uani 1 1 d . . . . .
F15 F -0.1490(3) 0.6464(9) 0.08141(19) 0.165(2) Uani 1 1 d . . . . .
F16 F -0.0250(3) 0.4067(6) 0.2501(3) 0.1129(10) Uani 1 1 d . . . . .
C21 C 0.2675(3) 0.4142(3) 0.6455(2) 0.0428(5) Uani 1 1 d . . . . .
N22 N 0.3660(3) 0.4774(3) 0.73652(18) 0.0450(4) Uani 1 1 d . . . . .
C23 C 0.4392(3) 0.3149(4) 0.78831(18) 0.0414(5) Uani 1 1 d . . . . .
C24 C 0.5556(3) 0.2935(5) 0.8890(2) 0.0541(6) Uani 1 1 d . . . . .
H24 H 0.596824 0.397874 0.932879 0.065 Uiso 1 1 calc R U . . .
C25 C 0.6069(4) 0.1102(6) 0.9208(2) 0.0680(9) Uani 1 1 d . . . . .
H25 H 0.683559 0.092057 0.987785 0.082 Uiso 1 1 calc R U . . .
C26 C 0.5488(4) -0.0451(5) 0.8571(3) 0.0671(8) Uani 1 1 d . . . . .
H26 H 0.588291 -0.164932 0.881952 0.080 Uiso 1 1 calc R U . . .
C27 C 0.4333(4) -0.0305(4) 0.7569(3) 0.0562(6) Uani 1 1 d . . . . .
H27 H 0.393650 -0.136447 0.714101 0.067 Uiso 1 1 calc R U . . .
C28 C 0.3801(3) 0.1540(4) 0.7243(2) 0.0421(5) Uani 1 1 d . . . . .
N29 N 0.2693(3) 0.2227(3) 0.63168(18) 0.0455(5) Uani 1 1 d . . . . .
H29 H 0.209(5) 0.163(6) 0.588(3) 0.065(10) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C11 1.500(4) . ?
C1 S2 1.826(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
O2 S2 1.4966(18) . ?
S2 C21 1.768(2) . ?
C11 C12 1.375(6) . ?
C11 C16 1.380(5) . ?
C12 F12 1.338(5) . ?
C12 C13 1.381(5) . ?
C13 F13 1.334(7) . ?
C13 C14 1.376(10) . ?
C14 F14 1.339(5) . ?
C14 C15 1.344(11) . ?
C15 F15 1.334(6) . ?
C15 C16 1.400(7) . ?
C16 F16 1.335(7) . ?
C21 N22 1.308(3) . ?
C21 N29 1.358(3) . ?
N22 C23 1.380(3) . ?
C23 C24 1.397(3) . ?
C23 C28 1.404(3) . ?
C24 C25 1.385(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.369(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.384(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.399(4) . ?
C27 H27 0.9300 . ?
C28 N29 1.380(3) . ?
N29 H29 0.77(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C1 S2 108.5(2) . . ?
C11 C1 H1A 110.0 . . ?
S2 C1 H1A 110.0 . . ?
C11 C1 H1B 110.0 . . ?
S2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
O2 S2 C21 108.27(11) . . ?
O2 S2 C1 104.76(14) . . ?
C21 S2 C1 96.35(12) . . ?
C12 C11 C16 118.1(4) . . ?
C12 C11 C1 120.5(3) . . ?
C16 C11 C1 121.5(4) . . ?
F12 C12 C11 119.6(3) . . ?
F12 C12 C13 118.1(5) . . ?
C11 C12 C13 122.3(4) . . ?
F13 C13 C14 121.3(5) . . ?
F13 C13 C12 120.5(6) . . ?
C14 C13 C12 118.1(5) . . ?
F14 C14 C15 119.6(7) . . ?
F14 C14 C13 119.1(8) . . ?
C15 C14 C13 121.3(4) . . ?
F15 C15 C14 121.2(5) . . ?
F15 C15 C16 118.7(7) . . ?
C14 C15 C16 120.1(5) . . ?
F16 C16 C11 120.5(4) . . ?
F16 C16 C15 119.5(5) . . ?
C11 C16 C15 120.0(6) . . ?
N22 C21 N29 115.0(2) . . ?
N22 C21 S2 118.80(19) . . ?
N29 C21 S2 126.13(19) . . ?
C21 N22 C23 103.8(2) . . ?
N22 C23 C24 130.0(2) . . ?
N22 C23 C28 110.3(2) . . ?
C24 C23 C28 119.8(2) . . ?
C25 C24 C23 117.2(3) . . ?
C25 C24 H24 121.4 . . ?
C23 C24 H24 121.4 . . ?
C26 C25 C24 122.3(2) . . ?
C26 C25 H25 118.8 . . ?
C24 C25 H25 118.8 . . ?
C25 C26 C27 122.4(3) . . ?
C25 C26 H26 118.8 . . ?
C27 C26 H26 118.8 . . ?
C26 C27 C28 115.7(3) . . ?
C26 C27 H27 122.1 . . ?
C28 C27 H27 122.1 . . ?
N29 C28 C27 132.0(2) . . ?
N29 C28 C23 105.4(2) . . ?
C27 C28 C23 122.6(2) . . ?
C21 N29 C28 105.5(2) . . ?
C21 N29 H29 127(3) . . ?
C28 N29 H29 126(3) . . ?

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.042



####################################################################### 
# 
# 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_9B
_database_code_depnum_ccdc_archive 'CCDC 2328884'
loop_
_audit_author_name
_audit_author_address
'Cosimo Cardellicchio'
;CNR ICCOM
Italy
;
_audit_update_record             
;
2024-01-27 deposited with the CCDC.	2024-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
2-(2,3,4,5,6-pentafluorobenzylsulfinyl)thiophene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H5 F5 O S2'
_chemical_formula_weight         312.27

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.4947(11)
_cell_length_b                   9.2154(18)
_cell_length_c                   23.473(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1188.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7177
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      28.51

_exptl_crystal_description       table
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.520
_exptl_crystal_size_min          0.270
_exptl_absorpt_coefficient_mu    0.499
_shelx_estimated_absorpt_T_min   0.691
_shelx_estimated_absorpt_T_max   0.877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS, 2.05'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker SMART-APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.13
_diffrn_reflns_number            9421
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_av_R_equivalents  0.0126
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.735
_diffrn_reflns_theta_max         28.709
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2891
_reflns_number_gt                2783
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_max     0.902
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SMART 5.6 (Bruker)'
_computing_cell_refinement       'SAINT 5.0 (Bruker)'
_computing_data_reduction        'SAINT 5.0 (Bruker)'
_computing_structure_solution    'SHELXTL-NT 6.1 (Bruker)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0907P)²+0.1207P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_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 1072 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.023(16)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2891
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1236
_refine_ls_wR_factor_gt          0.1218
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4658(7) 0.7019(4) 0.92131(14) 0.0552(7) Uani 1 1 d . . . . .
H1A H 0.444406 0.802158 0.932901 0.066 Uiso 1 1 calc R U . . .
H1B H 0.638452 0.680216 0.922885 0.066 Uiso 1 1 calc R U . . .
S2 S 0.30481(15) 0.58388(9) 0.97189(3) 0.0515(2) Uani 1 1 d . . . . .
O2 O 0.0393(5) 0.6077(3) 0.96317(12) 0.0644(6) Uani 1 1 d . . . . .
C11 C 0.3800(5) 0.6853(3) 0.86136(13) 0.0454(6) Uani 1 1 d . . . . .
C12 C 0.1712(6) 0.7544(3) 0.84129(14) 0.0500(6) Uani 1 1 d . . . . .
C13 C 0.0895(6) 0.7365(3) 0.78653(15) 0.0520(7) Uani 1 1 d . . . . .
C14 C 0.2153(6) 0.6464(3) 0.74940(13) 0.0526(7) Uani 1 1 d . . . . .
C15 C 0.4190(6) 0.5780(3) 0.76764(13) 0.0501(6) Uani 1 1 d . . . . .
C16 C 0.4977(5) 0.5961(3) 0.82293(13) 0.0469(6) Uani 1 1 d . . . . .
F12 F 0.0489(5) 0.8454(2) 0.87512(11) 0.0738(6) Uani 1 1 d . . . . .
F13 F -0.1112(4) 0.8049(3) 0.76810(12) 0.0778(7) Uani 1 1 d . . . . .
F14 F 0.1338(5) 0.6280(3) 0.69606(9) 0.0764(7) Uani 1 1 d . . . . .
F15 F 0.5436(5) 0.4919(3) 0.73188(10) 0.0729(6) Uani 1 1 d . . . . .
F16 F 0.7016(4) 0.5264(3) 0.83850(10) 0.0670(6) Uani 1 1 d . . . . .
C21 C 0.3728(5) 0.4128(3) 0.94187(11) 0.0437(5) Uani 1 1 d . . . . .
C22 C 0.5785(5) 0.3259(3) 0.95618(12) 0.0458(6) Uani 1 1 d . . . . .
H22 H 0.701194 0.349256 0.981890 0.055 Uiso 1 1 calc R U . . .
C23 C 0.5592(8) 0.1947(4) 0.92300(16) 0.0645(9) Uani 1 1 d . . . . .
H23 H 0.675955 0.121727 0.924129 0.077 Uiso 1 1 calc R U . . .
C24 C 0.3574(7) 0.1863(4) 0.89007(17) 0.0628(8) Uani 1 1 d . . . . .
H24 H 0.321304 0.106774 0.867179 0.075 Uiso 1 1 calc R U . . .
S25 S 0.17790(16) 0.33423(10) 0.89465(4) 0.0596(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C11 1.492(4) . ?
C1 S2 1.837(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
S2 O2 1.489(3) . ?
S2 C21 1.767(3) . ?
C11 C16 1.382(4) . ?
C11 C12 1.394(4) . ?
C12 F12 1.336(4) . ?
C12 C13 1.371(5) . ?
C13 F13 1.342(4) . ?
C13 C14 1.388(5) . ?
C14 F14 1.340(4) . ?
C14 C15 1.354(5) . ?
C15 F15 1.343(4) . ?
C15 C16 1.378(4) . ?
C16 F16 1.342(3) . ?
C21 C22 1.425(4) . ?
C21 S25 1.703(3) . ?
C22 C23 1.442(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.354(6) . ?
C23 H23 0.9300 . ?
C24 S25 1.686(4) . ?
C24 H24 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
C11 C1 S2 113.3(2) . . ?
C11 C1 H1A 108.9 . . ?
S2 C1 H1A 108.9 . . ?
C11 C1 H1B 108.9 . . ?
S2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
O2 S2 C21 106.48(15) . . ?
O2 S2 C1 107.20(17) . . ?
C21 S2 C1 99.73(15) . . ?
C16 C11 C12 115.9(3) . . ?
C16 C11 C1 121.9(3) . . ?
C12 C11 C1 122.1(3) . . ?
F12 C12 C13 117.9(3) . . ?
F12 C12 C11 120.0(3) . . ?
C13 C12 C11 122.1(3) . . ?
F13 C13 C12 121.0(3) . . ?
F13 C13 C14 119.2(3) . . ?
C12 C13 C14 119.8(3) . . ?
F14 C14 C15 120.8(3) . . ?
F14 C14 C13 119.7(3) . . ?
C15 C14 C13 119.4(3) . . ?
F15 C15 C14 119.9(3) . . ?
F15 C15 C16 120.0(3) . . ?
C14 C15 C16 120.1(3) . . ?
F16 C16 C15 117.4(3) . . ?
F16 C16 C11 119.9(3) . . ?
C15 C16 C11 122.7(3) . . ?
C22 C21 S25 114.4(2) . . ?
C22 C21 S2 125.1(2) . . ?
S25 C21 S2 120.39(17) . . ?
C21 C22 C23 106.6(3) . . ?
C21 C22 H22 126.7 . . ?
C23 C22 H22 126.7 . . ?
C24 C23 C22 114.6(3) . . ?
C24 C23 H23 122.7 . . ?
C22 C23 H23 122.7 . . ?
C23 C24 S25 113.3(3) . . ?
C23 C24 H24 123.3 . . ?
S25 C24 H24 123.3 . . ?
C24 S25 C21 91.00(18) . . ?

_refine_diff_density_max         0.534
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.071



####################################################################### 
# 
# 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_3B
_database_code_depnum_ccdc_archive 'CCDC 2328885'
loop_
_audit_author_name
_audit_author_address
'Cosimo Cardellicchio'
;CNR ICCOM
Italy
;
_audit_update_record             
;
2024-01-27 deposited with the CCDC.	2024-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        Benzylsulfinyl-1H-benzo[d]imidazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 N2 O S'
_chemical_formula_weight         256.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           172
_space_group_name_H-M_alt        'P 64'
_space_group_name_Hall           'P 64'

_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'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'-x, -y, z'
'y, -x+y, z+1/3'
'x-y, x, z+2/3'

_cell_length_a                   13.2625(10)
_cell_length_b                   13.2625(10)
_cell_length_c                   12.4674(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1899.1(3)
_cell_formula_units_Z            6
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    17959
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      17.46

_exptl_crystal_description       table
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             804
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.244
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8538
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   'SADABS, 2.05'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker SMART-APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.13
_diffrn_reflns_number            17934
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.773
_diffrn_reflns_theta_max         28.744
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3030
_reflns_number_gt                2017
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.855
_reflns_Friedel_fraction_max     0.888
_reflns_Friedel_fraction_full    0.996

_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       'SMART 5.6 (Bruker)'
_computing_cell_refinement       'SAINT 5.0 (Bruker)'
_computing_data_reduction        'SAINT 5.0 (Bruker)'
_computing_structure_solution    'SHELXTL-NT 6.1 (Bruker)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0375P)²+0.0302P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_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 666 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3030
_refine_ls_number_parameters     166
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1141
_refine_ls_R_factor_gt           0.0659
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0907
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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
C101 C 0.7020(4) 0.8347(4) 0.2363(3) 0.0559(13) Uani 1 1 d . . . . .
H10A H 0.692841 0.768538 0.277454 0.067 Uiso 1 1 calc R U . . .
H10B H 0.693264 0.886675 0.285256 0.067 Uiso 1 1 calc R U . . .
S102 S 0.84850(10) 0.91090(10) 0.17888(9) 0.0493(3) Uani 1 1 d . . . . .
O102 O 0.8487(3) 0.8396(3) 0.0865(3) 0.0644(9) Uani 1 1 d . . . . .
C111 C 0.6079(4) 0.7927(4) 0.1536(4) 0.0501(13) Uani 1 1 d . . . . .
C112 C 0.5789(4) 0.6937(4) 0.0955(4) 0.0648(14) Uani 1 1 d . . . . .
H112 H 0.615646 0.651251 0.110389 0.078 Uiso 1 1 calc R U . . .
C113 C 0.4960(4) 0.6564(6) 0.0153(5) 0.0818(17) Uani 1 1 d . . . . .
H113 H 0.478703 0.590064 -0.024013 0.098 Uiso 1 1 calc R U . . .
C114 C 0.4396(5) 0.7157(6) -0.0066(5) 0.0798(18) Uani 1 1 d . . . . .
H114 H 0.383199 0.689631 -0.059994 0.096 Uiso 1 1 calc R U . . .
C115 C 0.4661(5) 0.8139(6) 0.0502(5) 0.0810(18) Uani 1 1 d . . . . .
H115 H 0.427386 0.854540 0.035448 0.097 Uiso 1 1 calc R U . . .
C116 C 0.5516(4) 0.8538(5) 0.1309(4) 0.0667(16) Uani 1 1 d . . . . .
H116 H 0.570167 0.921301 0.168867 0.080 Uiso 1 1 calc R U . . .
C121 C 0.8389(4) 1.0277(4) 0.1180(3) 0.0402(10) Uani 1 1 d . . . . .
N122 N 0.8068(3) 1.0237(3) 0.0145(3) 0.0441(9) Uani 1 1 d . . . . .
H122 H 0.790(4) 0.969(4) -0.029(4) 0.053 Uiso 1 1 d . U . . .
C123 C 0.8167(3) 1.1289(4) -0.0079(3) 0.0426(11) Uani 1 1 d . . . . .
C124 C 0.7964(4) 1.1736(5) -0.1012(4) 0.0551(13) Uani 1 1 d . . . . .
H124 H 0.769473 1.129534 -0.163539 0.066 Uiso 1 1 calc R U . . .
C125 C 0.8182(5) 1.2863(5) -0.0963(5) 0.0653(15) Uani 1 1 d . . . . .
H125 H 0.804927 1.319223 -0.156711 0.078 Uiso 1 1 calc R U . . .
C126 C 0.8595(4) 1.3520(5) -0.0037(5) 0.0674(15) Uani 1 1 d . . . . .
H126 H 0.874367 1.428318 -0.004107 0.081 Uiso 1 1 calc R U . . .
C127 C 0.8794(4) 1.3082(5) 0.0889(5) 0.0613(13) Uani 1 1 d . . . . .
H127 H 0.906695 1.353224 0.150711 0.074 Uiso 1 1 calc R U . . .
C128 C 0.8567(4) 1.1931(4) 0.0864(3) 0.0455(11) Uani 1 1 d . . . . .
N129 N 0.8704(3) 1.1277(3) 0.1650(3) 0.0487(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C101 C111 1.496(6) . ?
C101 S102 1.829(5) . ?
C101 H10A 0.9700 . ?
C101 H10B 0.9700 . ?
S102 O102 1.490(3) . ?
S102 C121 1.786(5) . ?
C111 C112 1.375(7) . ?
C111 C116 1.377(7) . ?
C112 C113 1.381(7) . ?
C112 H112 0.9300 . ?
C113 C114 1.357(8) . ?
C113 H113 0.9300 . ?
C114 C115 1.364(8) . ?
C114 H114 0.9300 . ?
C115 C116 1.407(7) . ?
C115 H115 0.9300 . ?
C116 H116 0.9300 . ?
C121 N129 1.312(5) . ?
C121 N122 1.352(5) . ?
N122 C123 1.364(5) . ?
N122 H122 0.84(5) . ?
C123 C124 1.392(6) . ?
C123 C128 1.392(6) . ?
C124 C125 1.374(7) . ?
C124 H124 0.9300 . ?
C125 C126 1.384(8) . ?
C125 H125 0.9300 . ?
C126 C127 1.376(7) . ?
C126 H126 0.9300 . ?
C127 C128 1.401(6) . ?
C127 H127 0.9300 . ?
C128 N129 1.379(5) . ?

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
C111 C101 S102 113.2(3) . . ?
C111 C101 H10A 108.9 . . ?
S102 C101 H10A 108.9 . . ?
C111 C101 H10B 108.9 . . ?
S102 C101 H10B 108.9 . . ?
H10A C101 H10B 107.8 . . ?
O102 S102 C121 104.2(2) . . ?
O102 S102 C101 106.9(2) . . ?
C121 S102 C101 97.4(2) . . ?
C112 C111 C116 118.6(5) . . ?
C112 C111 C101 120.1(5) . . ?
C116 C111 C101 121.3(5) . . ?
C111 C112 C113 121.1(5) . . ?
C111 C112 H112 119.5 . . ?
C113 C112 H112 119.5 . . ?
C114 C113 C112 120.5(6) . . ?
C114 C113 H113 119.7 . . ?
C112 C113 H113 119.7 . . ?
C113 C114 C115 119.7(6) . . ?
C113 C114 H114 120.1 . . ?
C115 C114 H114 120.1 . . ?
C114 C115 C116 120.3(6) . . ?
C114 C115 H115 119.8 . . ?
C116 C115 H115 119.8 . . ?
C111 C116 C115 119.8(6) . . ?
C111 C116 H116 120.1 . . ?
C115 C116 H116 120.1 . . ?
N129 C121 N122 113.7(4) . . ?
N129 C121 S102 124.2(3) . . ?
N122 C121 S102 121.9(3) . . ?
C121 N122 C123 106.7(4) . . ?
C121 N122 H122 126(3) . . ?
C123 N122 H122 127(3) . . ?
N122 C123 C124 131.8(4) . . ?
N122 C123 C128 105.4(4) . . ?
C124 C123 C128 122.8(4) . . ?
C125 C124 C123 116.5(5) . . ?
C125 C124 H124 121.8 . . ?
C123 C124 H124 121.8 . . ?
C124 C125 C126 121.5(5) . . ?
C124 C125 H125 119.2 . . ?
C126 C125 H125 119.2 . . ?
C127 C126 C125 122.3(5) . . ?
C127 C126 H126 118.9 . . ?
C125 C126 H126 118.9 . . ?
C126 C127 C128 117.3(5) . . ?
C126 C127 H127 121.3 . . ?
C128 C127 H127 121.3 . . ?
N129 C128 C123 110.2(4) . . ?
N129 C128 C127 130.2(4) . . ?
C123 C128 C127 119.6(5) . . ?
C121 N129 C128 104.1(4) . . ?

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.037



