# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_BTR_I2
_database_code_depnum_ccdc_archive 'CCDC 2341835'
loop_
_audit_author_name
_audit_author_address
'Enrico Podda'
;University of Cagliari
Italy
;
_audit_update_record             
;
2024-03-20 deposited with the CCDC.	2024-06-17 downloaded from the CCDC.
;
_audit_creation_date             2024-02-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H11 I2 N O S4'
_chemical_formula_sum            'C14 H11 I2 N O S4'
_chemical_formula_weight         591.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9908(9)
_cell_length_b                   10.5236(10)
_cell_length_c                   11.0589(11)
_cell_angle_alpha                108.366(3)
_cell_angle_beta                 106.358(4)
_cell_angle_gamma                98.198(4)
_cell_volume                     921.59(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9863
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.48
_cell_measurement_theta_min      2.59
_shelx_estimated_absorpt_T_max   0.893
_shelx_estimated_absorpt_T_min   0.497
_exptl_absorpt_coefficient_mu    3.865
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.5626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1411 before and 0.0682 after correction.
The Ratio of minimum to maximum transmission is 0.7540.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.131
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27834
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.441
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON II area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3975
_reflns_number_total             4230
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         4230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0162
_refine_ls_R_factor_gt           0.0145
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0144P)²+0.4591P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0351
_refine_ls_wR_factor_ref         0.0360
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uanis(S4B) = Uanis(C12B)
2. Others
 Fixed Sof: S4B(0.15) S4A(0.85) C12A(0.85) C12B(0.15) H12B(0.15) H12A(0.85)
3.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C13(H13), C14(H14), C8(H8), C9(H9), C12B(H12B)
3.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.73570(2) 0.89445(2) 0.33179(2) 0.01568(4) Uani 1 1 d . . . . .
I2 I 0.66706(2) 0.68760(2) 0.07606(2) 0.02453(4) Uani 1 1 d . . . . .
S2 S 0.59879(5) 0.88874(4) 0.59993(4) 0.01566(8) Uani 1 1 d . . . . .
S1 S 0.82403(5) 1.11189(4) 0.57766(4) 0.01796(9) Uani 1 1 d . . . . .
S3 S 0.35194(5) 0.60903(4) 0.53127(4) 0.01840(9) Uani 1 1 d . . . . .
S4B S 0.2112(16) 0.3374(13) 0.2545(15) 0.0204(15) Uani 0.15 1 d . . P A 2
O1 O 0.66411(16) 1.10546(13) 0.96998(13) 0.0233(3) Uani 1 1 d . . . . .
N1 N 0.74736(17) 1.12195(14) 0.79587(14) 0.0153(3) Uani 1 1 d . . . . .
C1 C 0.7300(2) 1.05092(16) 0.66564(17) 0.0155(3) Uani 1 1 d . . . . .
C3 C 0.5670(2) 0.91533(17) 0.75415(17) 0.0162(3) Uani 1 1 d . . . . .
C2 C 0.6587(2) 1.05318(17) 0.85397(18) 0.0171(3) Uani 1 1 d . . . . .
C4 C 0.8502(2) 1.26320(17) 0.87497(18) 0.0194(3) Uani 1 1 d . . . . .
H4A H 0.950388 1.271568 0.854019 0.023 Uiso 1 1 calc R U . . .
H4B H 0.879240 1.280926 0.973123 0.023 Uiso 1 1 calc R U . . .
C6 C 0.4725(2) 0.82675(17) 0.78439(18) 0.0172(3) Uani 1 1 d . . . . .
H6 H 0.471509 0.860042 0.874529 0.021 Uiso 1 1 calc R U . . .
C10 C 0.2198(2) 0.46349(17) 0.51541(18) 0.0171(3) Uani 1 1 d . . . . .
C5 C 0.7669(3) 1.37093(18) 0.8434(2) 0.0275(4) Uani 1 1 d . . . . .
H5A H 0.741193 1.355432 0.746860 0.041 Uiso 1 1 calc R U . . .
H5B H 0.838002 1.463670 0.898603 0.041 Uiso 1 1 calc R U . . .
H5C H 0.667951 1.363113 0.864404 0.041 Uiso 1 1 calc R U . . .
C7 C 0.3745(2) 0.69083(17) 0.70046(17) 0.0174(3) Uani 1 1 d . . . . .
C11 C 0.1520(2) 0.34695(17) 0.38702(18) 0.0174(3) Uani 1 1 d . . . . .
C13 C 0.0961(2) 0.1934(2) 0.16517(19) 0.0238(4) Uani 1 1 d . . . . .
H13 H 0.105225 0.160094 0.077814 0.029 Uiso 1 1 calc R U . A 1
C14 C -0.0063(2) 0.12394(18) 0.20679(18) 0.0223(4) Uani 1 1 d . . . . .
H14 H -0.077666 0.035665 0.150629 0.027 Uiso 1 1 calc R U . A 1
C8 C 0.2824(2) 0.60642(18) 0.74013(19) 0.0220(4) Uani 1 1 d . . . . .
H8 H 0.278233 0.632416 0.829317 0.026 Uiso 1 1 calc R U . . .
C9 C 0.1956(2) 0.47882(18) 0.63594(19) 0.0224(4) Uani 1 1 d . . . . .
H9 H 0.126842 0.409650 0.647421 0.027 Uiso 1 1 calc R U . . .
S4A S 0.00594(11) 0.20980(9) 0.36791(9) 0.01852(15) Uani 0.85 1 d . . P A 1
C12A C 0.1862(12) 0.3209(10) 0.2686(11) 0.0230(14) Uani 0.85 1 d . . P A 1
C12B C 0.029(3) 0.226(2) 0.352(3) 0.0204(15) Uani 0.15 1 d . . P A 2
H12B H -0.023756 0.210219 0.411394 0.025 Uiso 0.15 1 calc R U P A 2
H12A H 0.276(3) 0.387(3) 0.266(2) 0.005(7) Uiso 0.85 1 d . . P B 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
I1 I2 2.8057(3) . ?
I1 S1 2.7576(5) . ?
S2 C1 1.7305(17) . ?
S2 C3 1.7510(17) . ?
S1 C1 1.6657(17) . ?
S3 C10 1.7270(17) . ?
S3 C7 1.7333(17) . ?
S4B C11 1.675(12) . ?
S4B C13 1.542(13) . ?
O1 C2 1.210(2) . ?
N1 C1 1.349(2) . ?
N1 C2 1.410(2) . ?
N1 C4 1.471(2) . ?
C3 C2 1.463(2) . ?
C3 C6 1.354(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.521(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.424(2) . ?
C10 C11 1.447(2) . ?
C10 C9 1.374(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C7 C8 1.382(2) . ?
C11 S4A 1.7215(19) . ?
C11 C12A 1.381(9) . ?
C11 C12B 1.43(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.361(3) . ?
C13 C12A 1.402(11) . ?
C14 H14 0.9500 . ?
C14 S4A 1.688(2) . ?
C14 C12B 1.54(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.400(3) . ?
C9 H9 0.9500 . ?
C12A H12A 1.00(3) . ?
C12B H12B 0.9500 . ?

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
S1 I1 I2 174.695(10) . . ?
C1 S2 C3 91.66(8) . . ?
C1 S1 I1 104.27(6) . . ?
C10 S3 C7 92.13(8) . . ?
C13 S4B C11 93.1(5) . . ?
C1 N1 C2 115.98(14) . . ?
C1 N1 C4 123.31(14) . . ?
C2 N1 C4 120.70(14) . . ?
S1 C1 S2 123.68(10) . . ?
N1 C1 S2 112.32(12) . . ?
N1 C1 S1 124.00(13) . . ?
C2 C3 S2 110.44(12) . . ?
C6 C3 S2 127.85(14) . . ?
C6 C3 C2 121.70(16) . . ?
O1 C2 N1 122.45(16) . . ?
O1 C2 C3 127.97(16) . . ?
N1 C2 C3 109.58(14) . . ?
N1 C4 H4A 109.3 . . ?
N1 C4 H4B 109.3 . . ?
N1 C4 C5 111.59(15) . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C6 H6 115.4 . . ?
C3 C6 C7 129.27(16) . . ?
C7 C6 H6 115.4 . . ?
C11 C10 S3 120.08(13) . . ?
C9 C10 S3 110.86(13) . . ?
C9 C10 C11 129.06(16) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C6 C7 S3 124.14(13) . . ?
C8 C7 S3 110.32(13) . . ?
C8 C7 C6 125.53(16) . . ?
C10 C11 S4B 122.8(4) . . ?
C10 C11 S4A 119.50(13) . . ?
C12A C11 C10 130.9(4) . . ?
C12A C11 S4A 109.6(4) . . ?
C12B C11 S4B 109.9(12) . . ?
C12B C11 C10 127.3(10) . . ?
C14 C13 S4B 123.9(4) . . ?
C14 C13 H13 124.6 . . ?
C14 C13 C12A 110.8(3) . . ?
C12A C13 H13 124.6 . . ?
C13 C14 H14 123.3 . . ?
C13 C14 S4A 113.48(14) . . ?
C13 C14 C12B 101.8(7) . . ?
S4A C14 H14 123.3 . . ?
C7 C8 H8 123.3 . . ?
C7 C8 C9 113.36(16) . . ?
C9 C8 H8 123.3 . . ?
C10 C9 C8 113.34(16) . . ?
C10 C9 H9 123.3 . . ?
C8 C9 H9 123.3 . . ?
C14 S4A C11 91.91(9) . . ?
C11 C12A C13 114.2(5) . . ?
C11 C12A H12A 119.5(18) . . ?
C13 C12A H12A 126.1(18) . . ?
C11 C12B C14 111.3(14) . . ?
C11 C12B H12B 124.3 . . ?
C14 C12B H12B 124.3 . . ?

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
I1 S1 C1 S2 -3.78(12) . . . . ?
I1 S1 C1 N1 176.20(13) . . . . ?
S2 C3 C2 O1 179.70(15) . . . . ?
S2 C3 C2 N1 -1.01(17) . . . . ?
S2 C3 C6 C7 -0.4(3) . . . . ?
S3 C10 C11 S4B 7.2(7) . . . . ?
S3 C10 C11 S4A -173.69(10) . . . . ?
S3 C10 C11 C12A 7.9(7) . . . . ?
S3 C10 C11 C12B -172.8(13) . . . . ?
S3 C10 C9 C8 0.1(2) . . . . ?
S3 C7 C8 C9 0.0(2) . . . . ?
S4B C11 C12B C14 2(2) . . . . ?
S4B C13 C14 C12B 0.1(9) . . . . ?
C1 S2 C3 C2 1.02(13) . . . . ?
C1 S2 C3 C6 -179.30(17) . . . . ?
C1 N1 C2 O1 179.79(16) . . . . ?
C1 N1 C2 C3 0.5(2) . . . . ?
C1 N1 C4 C5 81.2(2) . . . . ?
C3 S2 C1 S1 179.20(11) . . . . ?
C3 S2 C1 N1 -0.79(13) . . . . ?
C3 C6 C7 S3 -1.8(3) . . . . ?
C3 C6 C7 C8 179.38(18) . . . . ?
C2 N1 C1 S2 0.33(18) . . . . ?
C2 N1 C1 S1 -179.66(12) . . . . ?
C2 N1 C4 C5 -98.23(18) . . . . ?
C2 C3 C6 C7 179.23(17) . . . . ?
C4 N1 C1 S2 -179.09(12) . . . . ?
C4 N1 C1 S1 0.9(2) . . . . ?
C4 N1 C2 O1 -0.8(2) . . . . ?
C4 N1 C2 C3 179.89(14) . . . . ?
C6 C3 C2 O1 0.0(3) . . . . ?
C6 C3 C2 N1 179.29(15) . . . . ?
C6 C7 C8 C9 178.92(17) . . . . ?
C10 S3 C7 C6 -178.92(15) . . . . ?
C10 S3 C7 C8 0.06(14) . . . . ?
C10 C11 S4A C14 -179.04(14) . . . . ?
C10 C11 C12A C13 178.8(3) . . . . ?
C10 C11 C12B C14 -178.4(7) . . . . ?
C7 S3 C10 C11 -179.77(14) . . . . ?
C7 S3 C10 C9 -0.07(14) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
C11 S4B C13 C14 0.7(10) . . . . ?
C11 C10 C9 C8 179.72(17) . . . . ?
C13 S4B C11 C10 178.7(3) . . . . ?
C13 S4B C11 C12B -1.3(17) . . . . ?
C13 C14 S4A C11 0.32(16) . . . . ?
C13 C14 C12B C11 -1.1(17) . . . . ?
C14 C13 C12A C11 0.0(9) . . . . ?
C9 C10 C11 S4B -172.4(7) . . . . ?
C9 C10 C11 S4A 6.7(3) . . . . ?
C9 C10 C11 C12A -171.8(6) . . . . ?
C9 C10 C11 C12B 7.6(13) . . . . ?
S4A C11 C12A C13 0.2(9) . . . . ?
C12A C11 S4A C14 -0.3(5) . . . . ?
C12A C13 C14 S4A -0.3(5) . . . . ?

_olex2_submission_original_sample_id SUB1
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_BTR
_database_code_depnum_ccdc_archive 'CCDC 2341836'
loop_
_audit_author_name
_audit_author_address
'Enrico Podda'
;University of Cagliari
Italy
;
_audit_update_record             
;
2024-03-20 deposited with the CCDC.	2024-06-17 downloaded from the CCDC.
;
_audit_creation_date             2024-02-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H11 N O S4'
_chemical_formula_sum            'C14 H11 N O S4'
_chemical_formula_weight         337.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.1277(5)
_cell_length_b                   29.436(2)
_cell_length_c                   7.9018(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.267(3)
_cell_angle_gamma                90
_cell_volume                     1423.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7679
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      2.67
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.925
_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1047 before and 0.0708 after correction.
The Ratio of minimum to maximum transmission is 0.9005.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0689
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            26154
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         2.673
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON II area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2602
_reflns_number_total             3266
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0350
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0199P)²+1.1569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0751
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Sof(S5)=Sof(C15)=Sof(H15)=Sof(H14A)=Sof(H13A)=1-FVAR(1)
 Sof(S4)=Sof(H14)=Sof(H13)=Sof(C12)=Sof(H12)=FVAR(1)
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C9(H9), C8(H8), C14(H14), C14(H14A), C13(H13), C13(H13A), C12(H12),
 C6(H6)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S4A S 0.1306(10) 0.89633(19) 0.5971(8) 0.0190(8) Uani 0.357(3) 1 d . . P A 2
S3 S 0.24042(8) 0.75191(2) 0.61692(7) 0.01811(12) Uani 1 1 d . . . . .
S2 S 0.39385(8) 0.65366(2) 0.69745(7) 0.01847(12) Uani 1 1 d . . . . .
S1 S 0.65691(8) 0.57620(2) 0.83268(7) 0.02298(14) Uani 1 1 d . . . . .
S4B S 0.4878(3) 0.84343(6) 0.7308(2) 0.0202(3) Uani 0.643(3) 1 d . . P A 1
O1 O -0.0498(2) 0.57699(5) 0.49144(18) 0.0201(3) Uani 1 1 d . . . . .
N1 N 0.2761(2) 0.57080(6) 0.6478(2) 0.0166(4) Uani 1 1 d . . . . .
C12A C 0.4419(18) 0.8469(5) 0.7195(18) 0.022(4) Uiso 0.357(3) 1 d . . P A 2
H15 H 0.533372 0.821651 0.747657 0.027 Uiso 0.357(3) 1 calc R U P A 2
C7 C 0.0173(3) 0.72350(7) 0.5228(3) 0.0182(4) Uani 1 1 d . . . . .
C2 C 0.1051(3) 0.59509(7) 0.5654(2) 0.0167(4) Uani 1 1 d . . . . .
C3 C 0.1451(3) 0.64414(7) 0.5836(3) 0.0170(4) Uani 1 1 d . . . . .
C9 C -0.0747(3) 0.79945(7) 0.4861(3) 0.0205(4) Uani 1 1 d . . . . .
H9 H -0.163180 0.824409 0.448752 0.025 Uiso 1 1 calc R U . . .
C1 C 0.4408(3) 0.59559(7) 0.7260(3) 0.0180(4) Uani 1 1 d . . . . .
C11 C 0.2363(3) 0.84509(7) 0.6300(3) 0.0179(4) Uani 1 1 d . . . . .
C8 C -0.1351(3) 0.75410(7) 0.4592(3) 0.0213(5) Uani 1 1 d . . . . .
H8 H -0.269104 0.745298 0.402184 0.026 Uiso 1 1 calc R U . . .
C4 C 0.2732(3) 0.52107(7) 0.6504(3) 0.0189(4) Uani 1 1 d . . . . .
H4A H 0.424812 0.509555 0.647717 0.023 Uiso 1 1 calc R U . . .
H4B H 0.189994 0.509785 0.547812 0.023 Uiso 1 1 calc R U . . .
C14 C 0.4937(3) 0.89811(8) 0.7650(3) 0.0245(5) Uani 1 1 d . . . . .
H14 H 0.612803 0.912478 0.825829 0.029 Uiso 0.643(3) 1 calc R U P A 1
H14A H 0.620639 0.909853 0.824305 0.029 Uiso 0.357(3) 1 calc R U P A 2
C5 C 0.1709(3) 0.50298(7) 0.8062(3) 0.0236(5) Uani 1 1 d . . . . .
H5A H 0.164950 0.469737 0.800874 0.035 Uiso 1 1 calc R U . . .
H5B H 0.022413 0.515109 0.811057 0.035 Uiso 1 1 calc R U . . .
H5C H 0.258775 0.512355 0.907668 0.035 Uiso 1 1 calc R U . . .
C13 C 0.3190(4) 0.92157(8) 0.7013(3) 0.0251(5) Uani 1 1 d . . . . .
H13 H 0.302381 0.953629 0.706078 0.030 Uiso 0.643(3) 1 calc R U P A 1
H13A H 0.309945 0.953397 0.719694 0.030 Uiso 0.357(3) 1 calc R U P A 2
C12B C 0.158(2) 0.8897(4) 0.6235(16) 0.030(4) Uani 0.643(3) 1 d . . P A 1
H12 H 0.018831 0.898390 0.574949 0.035 Uiso 0.643(3) 1 calc R U P A 1
C6 C 0.0024(3) 0.67517(7) 0.5176(3) 0.0181(4) Uani 1 1 d . . . . .
H6 H -0.125166 0.663223 0.459759 0.022 Uiso 1 1 calc R U . . .
C10 C 0.1251(3) 0.80433(7) 0.5718(2) 0.0172(4) 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
S4A C11 1.656(7) . ?
S4A C13 1.567(6) . ?
S3 C7 1.734(2) . ?
S3 C10 1.726(2) . ?
S2 C3 1.748(2) . ?
S2 C1 1.746(2) . ?
S1 C1 1.632(2) . ?
S4B C11 1.695(3) . ?
S4B C14 1.632(3) . ?
O1 C2 1.210(2) . ?
N1 C2 1.398(2) . ?
N1 C1 1.365(3) . ?
N1 C4 1.464(2) . ?
C12A H15 0.9500 . ?
C12A C11 1.410(11) . ?
C12A C14 1.577(15) . ?
C7 C8 1.372(3) . ?
C7 C6 1.426(3) . ?
C2 C3 1.470(3) . ?
C3 C6 1.349(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.398(3) . ?
C9 C10 1.373(3) . ?
C11 C12B 1.399(12) . ?
C11 C10 1.442(3) . ?
C8 H8 0.9500 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.510(3) . ?
C14 H14 0.9500 . ?
C14 H14A 0.9500 . ?
C14 C13 1.347(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C13 H13 0.9500 . ?
C13 H13A 0.9500 . ?
C13 C12B 1.469(14) . ?
C12B H12 0.9500 . ?
C6 H6 0.9500 . ?

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
C13 S4A C11 94.6(4) . . ?
C10 S3 C7 92.24(10) . . ?
C1 S2 C3 92.40(10) . . ?
C14 S4B C11 93.47(14) . . ?
C2 N1 C4 120.57(16) . . ?
C1 N1 C2 116.90(17) . . ?
C1 N1 C4 122.52(16) . . ?
C11 C12A H15 125.9 . . ?
C11 C12A C14 108.3(8) . . ?
C14 C12A H15 125.9 . . ?
C8 C7 S3 110.12(15) . . ?
C8 C7 C6 127.10(19) . . ?
C6 C7 S3 122.78(15) . . ?
O1 C2 N1 123.10(19) . . ?
O1 C2 C3 127.00(18) . . ?
N1 C2 C3 109.90(17) . . ?
C2 C3 S2 110.09(14) . . ?
C6 C3 S2 128.15(16) . . ?
C6 C3 C2 121.76(18) . . ?
C8 C9 H9 123.3 . . ?
C10 C9 H9 123.3 . . ?
C10 C9 C8 113.31(19) . . ?
S1 C1 S2 122.15(12) . . ?
N1 C1 S2 110.67(14) . . ?
N1 C1 S1 127.18(16) . . ?
C12A C11 S4A 112.0(6) . . ?
C12A C11 C10 125.7(6) . . ?
C12B C11 S4B 110.2(6) . . ?
C12B C11 C10 128.0(6) . . ?
C10 C11 S4A 122.3(2) . . ?
C10 C11 S4B 121.76(16) . . ?
C7 C8 C9 113.73(18) . . ?
C7 C8 H8 123.1 . . ?
C9 C8 H8 123.1 . . ?
N1 C4 H4A 109.3 . . ?
N1 C4 H4B 109.3 . . ?
N1 C4 C5 111.68(17) . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
S4B C14 H14 122.1 . . ?
C12A C14 H14A 127.5 . . ?
C13 C14 S4B 115.73(18) . . ?
C13 C14 C12A 105.0(4) . . ?
C13 C14 H14 122.1 . . ?
C13 C14 H14A 127.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
S4A C13 H13A 120.0 . . ?
C14 C13 S4A 119.9(3) . . ?
C14 C13 H13 125.4 . . ?
C14 C13 H13A 120.0 . . ?
C14 C13 C12B 109.2(5) . . ?
C12B C13 H13 125.4 . . ?
C11 C12B C13 111.3(9) . . ?
C11 C12B H12 124.3 . . ?
C13 C12B H12 124.3 . . ?
C7 C6 H6 115.7 . . ?
C3 C6 C7 128.70(19) . . ?
C3 C6 H6 115.7 . . ?
C9 C10 S3 110.59(15) . . ?
C9 C10 C11 129.51(19) . . ?
C11 C10 S3 119.85(15) . . ?

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
S4A C11 C10 S3 -177.8(3) . . . . ?
S4A C11 C10 C9 -0.7(4) . . . . ?
S3 C7 C8 C9 -0.3(2) . . . . ?
S3 C7 C6 C3 1.9(3) . . . . ?
S2 C3 C6 C7 0.2(3) . . . . ?
S4B C11 C12B C13 1.5(11) . . . . ?
S4B C11 C10 S3 4.3(3) . . . . ?
S4B C11 C10 C9 -178.60(19) . . . . ?
S4B C14 C13 C12B 3.3(6) . . . . ?
O1 C2 C3 S2 -178.74(18) . . . . ?
O1 C2 C3 C6 1.0(3) . . . . ?
N1 C2 C3 S2 1.3(2) . . . . ?
N1 C2 C3 C6 -178.99(19) . . . . ?
C12A C11 C10 S3 2.1(8) . . . . ?
C12A C11 C10 C9 179.2(7) . . . . ?
C12A C14 C13 S4A -3.8(6) . . . . ?
C7 S3 C10 C9 -0.82(17) . . . . ?
C7 S3 C10 C11 176.78(17) . . . . ?
C2 N1 C1 S2 -1.1(2) . . . . ?
C2 N1 C1 S1 179.14(15) . . . . ?
C2 N1 C4 C5 -92.7(2) . . . . ?
C2 C3 C6 C7 -179.5(2) . . . . ?
C3 S2 C1 S1 -178.67(14) . . . . ?
C3 S2 C1 N1 1.54(16) . . . . ?
C1 S2 C3 C2 -1.60(15) . . . . ?
C1 S2 C3 C6 178.7(2) . . . . ?
C1 N1 C2 O1 179.88(19) . . . . ?
C1 N1 C2 C3 -0.1(2) . . . . ?
C1 N1 C4 C5 86.5(2) . . . . ?
C11 S4A C13 C14 4.9(4) . . . . ?
C11 S4B C14 C13 -2.2(2) . . . . ?
C11 C12A C14 C13 0.4(9) . . . . ?
C8 C7 C6 C3 -177.5(2) . . . . ?
C8 C9 C10 S3 0.8(2) . . . . ?
C8 C9 C10 C11 -176.5(2) . . . . ?
C4 N1 C2 O1 -0.9(3) . . . . ?
C4 N1 C2 C3 179.07(17) . . . . ?
C4 N1 C1 S2 179.73(14) . . . . ?
C4 N1 C1 S1 0.0(3) . . . . ?
C14 S4B C11 C12B 0.2(7) . . . . ?
C14 S4B C11 C10 -176.51(18) . . . . ?
C14 C12A C11 S4A 2.7(10) . . . . ?
C14 C12A C11 C10 -177.2(4) . . . . ?
C14 C13 C12B C11 -3.0(11) . . . . ?
C13 S4A C11 C12A -4.2(7) . . . . ?
C13 S4A C11 C10 175.7(2) . . . . ?
C12B C11 C10 S3 -171.8(7) . . . . ?
C12B C11 C10 C9 5.3(8) . . . . ?
C6 C7 C8 C9 179.1(2) . . . . ?
C10 S3 C7 C8 0.64(17) . . . . ?
C10 S3 C7 C6 -178.82(18) . . . . ?
C10 C9 C8 C7 -0.3(3) . . . . ?
C10 C11 C12B C13 178.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
