# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_m2
_database_code_depnum_ccdc_archive 'CCDC 1991748'
loop_
_audit_author_name
_audit_author_address
'Changting Wen'
;Northwest University
China
;
_audit_update_record             
;
2023-06-07 deposited with the CCDC.	2024-06-04 downloaded from the CCDC.
;
_audit_creation_date             2019-07-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H10 F N3 S'
_chemical_formula_sum            'C17 H10 F N3 S'
_chemical_formula_weight         307.34
_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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.140(2)
_cell_length_b                   15.767(4)
_cell_length_c                   9.982(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.097(5)
_cell_angle_gamma                90
_cell_volume                     1411.6(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    613
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.95
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0712 before and 0.0531 after correction. The Ratio of minimum to maximum transmission is 0.8802. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7527
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.097
_diffrn_reflns_theta_min         2.448
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1369
_reflns_number_total             2789
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2789
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1314
_refine_ls_R_factor_gt           0.0520
_refine_ls_restrained_S_all      0.951
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0494P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1336
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C14(H14),
 C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.29637(9) -0.04492(5) -0.41265(9) 0.0631(3) Uani 1 1 d . . . . .
F1 F 0.4990(2) -0.56415(11) -0.3270(2) 0.0858(7) Uani 1 1 d . . . . .
N1 N 0.5558(3) -0.01779(18) -0.2756(3) 0.0763(9) Uani 1 1 d . . . . .
N2 N 0.4933(3) 0.06118(17) -0.3070(3) 0.0736(9) Uani 1 1 d . . . . .
N3 N 0.3972(3) -0.22228(15) -0.3626(3) 0.0510(7) Uani 1 1 d . . . . .
C1 C 0.2688(3) 0.13295(18) -0.4245(3) 0.0502(8) Uani 1 1 d . . . . .
C2 C 0.5060(3) -0.1692(2) -0.3105(3) 0.0512(8) Uani 1 1 d . . . . .
C3 C 0.3375(4) -0.4497(2) -0.3973(3) 0.0625(9) Uani 1 1 d . . . . .
H3 H 0.262094 -0.487528 -0.433362 0.075 Uiso 1 1 calc R . . . .
C4 C 0.4279(3) -0.30699(19) -0.3510(3) 0.0506(8) Uani 1 1 d . . . . .
C5 C 0.2473(4) 0.2840(2) -0.4373(4) 0.0709(10) Uani 1 1 d . . . . .
H5 H 0.288866 0.337299 -0.415707 0.085 Uiso 1 1 calc R . . . .
C6 C 0.6797(4) -0.2792(2) -0.2344(3) 0.0631(10) Uani 1 1 d . . . . .
H6 H 0.773746 -0.297777 -0.191740 0.076 Uiso 1 1 calc R . . . .
C7 C 0.3138(4) -0.36470(19) -0.4051(3) 0.0567(9) Uani 1 1 d . . . . .
H7 H 0.220761 -0.344152 -0.446740 0.068 Uiso 1 1 calc R . . . .
C8 C 0.5685(3) -0.3384(2) -0.2871(3) 0.0523(8) Uani 1 1 d . . . . .
C9 C 0.6496(3) -0.1949(2) -0.2460(3) 0.0598(9) Uani 1 1 d . . . . .
H9 H 0.722341 -0.155024 -0.212037 0.072 Uiso 1 1 calc R . . . .
C10 C 0.0428(4) 0.1989(2) -0.5419(4) 0.0716(11) Uani 1 1 d . . . . .
H10 H -0.054372 0.194175 -0.590766 0.086 Uiso 1 1 calc R . . . .
C11 C 0.3580(4) 0.05703(18) -0.3775(3) 0.0521(8) Uani 1 1 d . . . . .
C12 C 0.1243(4) 0.12679(19) -0.4992(3) 0.0614(9) Uani 1 1 d . . . . .
H12 H 0.082104 0.073640 -0.520683 0.074 Uiso 1 1 calc R . . . .
C13 C 0.4661(3) -0.0794(2) -0.3253(3) 0.0541(9) Uani 1 1 d . . . . .
C14 C 0.5921(4) -0.4274(2) -0.2804(3) 0.0615(10) Uani 1 1 d . . . . .
H14 H 0.684228 -0.449761 -0.240093 0.074 Uiso 1 1 calc R . . . .
C15 C 0.4776(4) -0.4787(2) -0.3339(3) 0.0612(10) Uani 1 1 d . . . . .
C16 C 0.3295(4) 0.2123(2) -0.3937(4) 0.0629(9) Uani 1 1 d . . . . .
H16 H 0.425892 0.217571 -0.343511 0.075 Uiso 1 1 calc R . . . .
C17 C 0.1052(4) 0.2777(2) -0.5121(4) 0.0714(11) Uani 1 1 d . . . . .
H17 H 0.051409 0.326347 -0.542536 0.086 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C11 1.717(3) . ?
S1 C13 1.715(3) . ?
F1 C15 1.361(3) . ?
N1 N2 1.380(3) . ?
N1 C13 1.306(4) . ?
N2 C11 1.301(4) . ?
N3 C2 1.327(4) . ?
N3 C4 1.365(3) . ?
C1 C11 1.473(4) . ?
C1 C12 1.390(4) . ?
C1 C16 1.379(4) . ?
C2 C9 1.406(4) . ?
C2 C13 1.462(4) . ?
C3 H3 0.9300 . ?
C3 C7 1.357(4) . ?
C3 C15 1.392(4) . ?
C4 C7 1.411(4) . ?
C4 C8 1.410(4) . ?
C5 H5 0.9300 . ?
C5 C16 1.380(4) . ?
C5 C17 1.372(5) . ?
C6 H6 0.9300 . ?
C6 C8 1.405(4) . ?
C6 C9 1.359(4) . ?
C7 H7 0.9300 . ?
C8 C14 1.419(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C10 C12 1.381(4) . ?
C10 C17 1.376(4) . ?
C12 H12 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.350(4) . ?
C16 H16 0.9300 . ?
C17 H17 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
C13 S1 C11 87.90(16) . . ?
C13 N1 N2 112.5(3) . . ?
C11 N2 N1 112.7(3) . . ?
C2 N3 C4 117.2(2) . . ?
C12 C1 C11 121.7(3) . . ?
C16 C1 C11 119.5(3) . . ?
C16 C1 C12 118.9(3) . . ?
N3 C2 C9 124.1(3) . . ?
N3 C2 C13 114.7(3) . . ?
C9 C2 C13 121.2(3) . . ?
C7 C3 H3 120.9 . . ?
C7 C3 C15 118.3(3) . . ?
C15 C3 H3 120.9 . . ?
N3 C4 C7 118.3(3) . . ?
N3 C4 C8 122.5(3) . . ?
C8 C4 C7 119.2(3) . . ?
C16 C5 H5 119.6 . . ?
C17 C5 H5 119.6 . . ?
C17 C5 C16 120.8(3) . . ?
C8 C6 H6 120.1 . . ?
C9 C6 H6 120.1 . . ?
C9 C6 C8 119.9(3) . . ?
C3 C7 C4 121.1(3) . . ?
C3 C7 H7 119.4 . . ?
C4 C7 H7 119.4 . . ?
C4 C8 C14 119.1(3) . . ?
C6 C8 C4 117.8(3) . . ?
C6 C8 C14 123.1(3) . . ?
C2 C9 H9 120.8 . . ?
C6 C9 C2 118.5(3) . . ?
C6 C9 H9 120.8 . . ?
C12 C10 H10 120.0 . . ?
C17 C10 H10 120.0 . . ?
C17 C10 C12 120.0(3) . . ?
N2 C11 S1 113.4(2) . . ?
N2 C11 C1 122.8(3) . . ?
C1 C11 S1 123.8(2) . . ?
C1 C12 H12 119.7 . . ?
C10 C12 C1 120.6(3) . . ?
C10 C12 H12 119.7 . . ?
N1 C13 S1 113.4(2) . . ?
N1 C13 C2 123.8(3) . . ?
C2 C13 S1 122.8(2) . . ?
C8 C14 H14 120.8 . . ?
C15 C14 C8 118.4(3) . . ?
C15 C14 H14 120.8 . . ?
F1 C15 C3 117.4(3) . . ?
C14 C15 F1 118.7(3) . . ?
C14 C15 C3 123.9(3) . . ?
C1 C16 C5 120.1(3) . . ?
C1 C16 H16 119.9 . . ?
C5 C16 H16 119.9 . . ?
C5 C17 C10 119.6(3) . . ?
C5 C17 H17 120.2 . . ?
C10 C17 H17 120.2 . . ?

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
N1 N2 C11 S1 -0.6(4) . . . . ?
N1 N2 C11 C1 -179.3(3) . . . . ?
N2 N1 C13 S1 -0.9(4) . . . . ?
N2 N1 C13 C2 178.2(3) . . . . ?
N3 C2 C9 C6 -0.7(5) . . . . ?
N3 C2 C13 S1 -4.0(4) . . . . ?
N3 C2 C13 N1 177.0(3) . . . . ?
N3 C4 C7 C3 179.7(3) . . . . ?
N3 C4 C8 C6 -0.2(5) . . . . ?
N3 C4 C8 C14 -179.4(3) . . . . ?
C2 N3 C4 C7 179.7(3) . . . . ?
C2 N3 C4 C8 -0.1(4) . . . . ?
C4 N3 C2 C9 0.6(5) . . . . ?
C4 N3 C2 C13 -179.6(3) . . . . ?
C4 C8 C14 C15 -1.0(5) . . . . ?
C6 C8 C14 C15 179.9(3) . . . . ?
C7 C3 C15 F1 179.9(3) . . . . ?
C7 C3 C15 C14 -0.5(5) . . . . ?
C7 C4 C8 C6 180.0(3) . . . . ?
C7 C4 C8 C14 0.8(5) . . . . ?
C8 C4 C7 C3 -0.4(5) . . . . ?
C8 C6 C9 C2 0.3(5) . . . . ?
C8 C14 C15 F1 -179.6(3) . . . . ?
C8 C14 C15 C3 0.9(5) . . . . ?
C9 C2 C13 S1 175.7(3) . . . . ?
C9 C2 C13 N1 -3.3(5) . . . . ?
C9 C6 C8 C4 0.1(5) . . . . ?
C9 C6 C8 C14 179.2(3) . . . . ?
C11 S1 C13 N1 0.5(3) . . . . ?
C11 S1 C13 C2 -178.6(3) . . . . ?
C11 C1 C12 C10 179.8(3) . . . . ?
C11 C1 C16 C5 179.9(3) . . . . ?
C12 C1 C11 S1 1.7(5) . . . . ?
C12 C1 C11 N2 -179.7(3) . . . . ?
C12 C1 C16 C5 -0.3(5) . . . . ?
C12 C10 C17 C5 -1.5(6) . . . . ?
C13 S1 C11 N2 0.0(3) . . . . ?
C13 S1 C11 C1 178.7(3) . . . . ?
C13 N1 N2 C11 1.0(4) . . . . ?
C13 C2 C9 C6 179.5(3) . . . . ?
C15 C3 C7 C4 0.3(5) . . . . ?
C16 C1 C11 S1 -178.5(3) . . . . ?
C16 C1 C11 N2 0.1(5) . . . . ?
C16 C1 C12 C10 0.0(5) . . . . ?
C16 C5 C17 C10 1.2(6) . . . . ?
C17 C5 C16 C1 -0.3(6) . . . . ?
C17 C10 C12 C1 0.9(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_m3
_database_code_depnum_ccdc_archive 'CCDC 2268163'
loop_
_audit_author_name
_audit_author_address
'Changting Wen'
;Northwest University
China
;
_audit_update_record             
;
2023-06-07 deposited with the CCDC.	2024-06-04 downloaded from the CCDC.
;
_audit_creation_date             2021-12-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H10 Br N3 S, 0.3[CHCl3]'
_chemical_formula_sum            'C17.30 H10.30 Br Cl0.90 N3 S'
_chemical_formula_weight         404.06
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br Br -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3281 0.5435 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.47(2)
_cell_length_b                   3.862(3)
_cell_length_c                   32.65(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.657(7)
_cell_angle_gamma                90
_cell_volume                     3220(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8859
_cell_measurement_temperature    220.00
_cell_measurement_theta_max      54.623
_cell_measurement_theta_min      2.529
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.026
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1693 before and 0.0511 after correction.
The Ratio of minimum to maximum transmission is 0.6974.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1611
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            24073
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.965
_diffrn_reflns_theta_min         2.533
_diffrn_ambient_temperature      220.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_source                   ?
_diffrn_source_current           2.23
_diffrn_source_power             0.1557878
_diffrn_source_voltage           69.86
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2501
_reflns_number_total             3068
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3068
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.037
_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)+(0.0417P)²+3.6824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0825
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17)
;
_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
Br1 Br 0.65244(2) 0.02193(7) 0.76009(2) 0.04645(12) Uani 1 1 d . . . . .
S1 S 0.66139(2) 0.89586(18) 0.50872(2) 0.03554(16) Uani 1 1 d . . . . .
N1 N 0.64614(8) 0.6317(5) 0.58814(6) 0.0320(4) Uani 1 1 d . . . . .
N2 N 0.57489(9) 1.0383(6) 0.44687(7) 0.0457(6) Uani 1 1 d . . . . .
N3 N 0.56175(8) 0.9126(7) 0.48088(7) 0.0462(6) Uani 1 1 d . . . . .
C1 C 0.60024(9) 0.6870(6) 0.55614(7) 0.0323(5) Uani 1 1 d . . . . .
C2 C 0.63988(12) 1.4305(7) 0.35658(9) 0.0470(7) Uani 1 1 d . . . . .
H2 H 0.618521 1.532991 0.329879 0.056 Uiso 1 1 calc R U . . .
C3 C 0.61803(11) 1.3184(7) 0.38606(8) 0.0428(6) Uani 1 1 d . . . . .
H3 H 0.581891 1.345009 0.379380 0.051 Uiso 1 1 calc R U . . .
C4 C 0.64529(10) 0.4936(6) 0.62629(7) 0.0311(5) Uani 1 1 d . . . . .
C5 C 0.62505(10) 1.0432(6) 0.45637(7) 0.0330(6) Uani 1 1 d . . . . .
C6 C 0.59838(10) 0.4027(7) 0.63189(8) 0.0338(5) Uani 1 1 d . . . . .
C7 C 0.72439(11) 1.2425(8) 0.40529(8) 0.0455(7) Uani 1 1 d . . . . .
H7 H 0.760487 1.215937 0.411784 0.055 Uiso 1 1 calc R U . . .
C8 C 0.60270(9) 0.8296(7) 0.51528(7) 0.0330(5) Uani 1 1 d . . . . .
C9 C 0.70257(10) 1.1314(7) 0.43491(8) 0.0405(6) Uani 1 1 d . . . . .
H9 H 0.724087 1.030850 0.461700 0.049 Uiso 1 1 calc R U . . .
C10 C 0.64864(10) 0.2103(6) 0.70526(7) 0.0355(6) Uani 1 1 d . . . . .
C11 C 0.55153(10) 0.6144(7) 0.55900(8) 0.0405(6) Uani 1 1 d . . . . .
H11 H 0.520190 0.665527 0.535423 0.049 Uiso 1 1 calc R U . . .
C12 C 0.69374(10) 0.4403(6) 0.66147(8) 0.0354(6) Uani 1 1 d . . . . .
H12 H 0.725153 0.502125 0.658114 0.043 Uiso 1 1 calc R U . . .
C13 C 0.55069(10) 0.4687(7) 0.59659(8) 0.0414(6) Uani 1 1 d . . . . .
H13 H 0.518622 0.412206 0.599093 0.050 Uiso 1 1 calc R U . . .
C14 C 0.69511(10) 0.3002(7) 0.70010(7) 0.0380(6) Uani 1 1 d . . . . .
H14 H 0.727399 0.264160 0.723287 0.046 Uiso 1 1 calc R U . . .
C15 C 0.69284(12) 1.3933(7) 0.36598(9) 0.0452(7) Uani 1 1 d . . . . .
H15 H 0.707486 1.470180 0.345729 0.054 Uiso 1 1 calc R U . . .
C16 C 0.64921(10) 1.1663(6) 0.42561(7) 0.0338(5) Uani 1 1 d . . . . .
C17 C 0.60097(10) 0.2571(7) 0.67240(8) 0.0381(6) Uani 1 1 d . . . . .
H17 H 0.570148 0.193136 0.676640 0.046 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
Br1 C10 1.899(3) . ?
S1 C5 1.727(3) . ?
S1 C8 1.722(3) . ?
N1 C1 1.325(3) . ?
N1 C4 1.363(3) . ?
N2 N3 1.376(3) . ?
N2 C5 1.296(4) . ?
N3 C8 1.303(3) . ?
C1 C8 1.468(3) . ?
C1 C11 1.404(4) . ?
C2 H2 0.9400 . ?
C2 C3 1.379(4) . ?
C2 C15 1.379(4) . ?
C3 H3 0.9400 . ?
C3 C16 1.389(3) . ?
C4 C6 1.411(4) . ?
C4 C12 1.416(3) . ?
C5 C16 1.472(3) . ?
C6 C13 1.412(4) . ?
C6 C17 1.415(3) . ?
C7 H7 0.9400 . ?
C7 C9 1.381(4) . ?
C7 C15 1.384(4) . ?
C9 H9 0.9400 . ?
C9 C16 1.390(4) . ?
C10 C14 1.392(4) . ?
C10 C17 1.364(3) . ?
C11 H11 0.9400 . ?
C11 C13 1.358(4) . ?
C12 H12 0.9400 . ?
C12 C14 1.360(4) . ?
C13 H13 0.9400 . ?
C14 H14 0.9400 . ?
C15 H15 0.9400 . ?
C17 H17 0.9400 . ?

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
C8 S1 C5 86.92(12) . . ?
C1 N1 C4 116.8(2) . . ?
C5 N2 N3 112.6(2) . . ?
C8 N3 N2 112.5(2) . . ?
N1 C1 C8 115.3(2) . . ?
N1 C1 C11 124.7(2) . . ?
C11 C1 C8 120.0(2) . . ?
C3 C2 H2 119.8 . . ?
C3 C2 C15 120.5(3) . . ?
C15 C2 H2 119.8 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C16 120.2(3) . . ?
C16 C3 H3 119.9 . . ?
N1 C4 C6 122.7(2) . . ?
N1 C4 C12 118.1(2) . . ?
C6 C4 C12 119.2(2) . . ?
N2 C5 S1 114.02(18) . . ?
N2 C5 C16 123.3(2) . . ?
C16 C5 S1 122.7(2) . . ?
C4 C6 C13 117.7(2) . . ?
C4 C6 C17 119.1(2) . . ?
C13 C6 C17 123.1(2) . . ?
C9 C7 H7 120.2 . . ?
C9 C7 C15 119.7(3) . . ?
C15 C7 H7 120.2 . . ?
N3 C8 S1 113.98(19) . . ?
N3 C8 C1 124.2(2) . . ?
C1 C8 S1 121.87(17) . . ?
C7 C9 H9 119.6 . . ?
C7 C9 C16 120.8(2) . . ?
C16 C9 H9 119.6 . . ?
C14 C10 Br1 118.42(18) . . ?
C17 C10 Br1 119.67(19) . . ?
C17 C10 C14 121.9(2) . . ?
C1 C11 H11 120.7 . . ?
C13 C11 C1 118.5(2) . . ?
C13 C11 H11 120.7 . . ?
C4 C12 H12 119.8 . . ?
C14 C12 C4 120.4(2) . . ?
C14 C12 H12 119.8 . . ?
C6 C13 H13 120.3 . . ?
C11 C13 C6 119.5(2) . . ?
C11 C13 H13 120.3 . . ?
C10 C14 H14 120.0 . . ?
C12 C14 C10 119.9(2) . . ?
C12 C14 H14 120.0 . . ?
C2 C15 C7 119.9(3) . . ?
C2 C15 H15 120.1 . . ?
C7 C15 H15 120.1 . . ?
C3 C16 C5 119.5(2) . . ?
C3 C16 C9 118.9(2) . . ?
C9 C16 C5 121.6(2) . . ?
C6 C17 H17 120.3 . . ?
C10 C17 C6 119.4(2) . . ?
C10 C17 H17 120.3 . . ?

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
Br1 C10 C14 C12 -179.07(19) . . . . ?
Br1 C10 C17 C6 178.98(19) . . . . ?
S1 C5 C16 C3 -172.5(2) . . . . ?
S1 C5 C16 C9 8.1(3) . . . . ?
N1 C1 C8 S1 3.5(3) . . . . ?
N1 C1 C8 N3 -177.4(2) . . . . ?
N1 C1 C11 C13 -1.8(4) . . . . ?
N1 C4 C6 C13 -1.8(4) . . . . ?
N1 C4 C6 C17 179.3(2) . . . . ?
N1 C4 C12 C14 -179.4(2) . . . . ?
N2 N3 C8 S1 -0.5(3) . . . . ?
N2 N3 C8 C1 -179.6(2) . . . . ?
N2 C5 C16 C3 6.8(4) . . . . ?
N2 C5 C16 C9 -172.6(2) . . . . ?
N3 N2 C5 S1 -0.5(3) . . . . ?
N3 N2 C5 C16 -179.9(2) . . . . ?
C1 N1 C4 C6 1.7(3) . . . . ?
C1 N1 C4 C12 -178.4(2) . . . . ?
C1 C11 C13 C6 1.6(4) . . . . ?
C2 C3 C16 C5 -179.0(2) . . . . ?
C2 C3 C16 C9 0.4(4) . . . . ?
C3 C2 C15 C7 0.0(4) . . . . ?
C4 N1 C1 C8 -178.9(2) . . . . ?
C4 N1 C1 C11 0.2(4) . . . . ?
C4 C6 C13 C11 0.1(4) . . . . ?
C4 C6 C17 C10 0.6(4) . . . . ?
C4 C12 C14 C10 -0.4(4) . . . . ?
C5 S1 C8 N3 0.1(2) . . . . ?
C5 S1 C8 C1 179.3(2) . . . . ?
C5 N2 N3 C8 0.6(3) . . . . ?
C6 C4 C12 C14 0.6(4) . . . . ?
C7 C9 C16 C3 -0.6(4) . . . . ?
C7 C9 C16 C5 178.8(2) . . . . ?
C8 S1 C5 N2 0.2(2) . . . . ?
C8 S1 C5 C16 179.6(2) . . . . ?
C8 C1 C11 C13 177.2(2) . . . . ?
C9 C7 C15 C2 -0.2(4) . . . . ?
C11 C1 C8 S1 -175.5(2) . . . . ?
C11 C1 C8 N3 3.5(4) . . . . ?
C12 C4 C6 C13 178.2(2) . . . . ?
C12 C4 C6 C17 -0.7(4) . . . . ?
C13 C6 C17 C10 -178.3(2) . . . . ?
C14 C10 C17 C6 -0.3(4) . . . . ?
C15 C2 C3 C16 0.0(4) . . . . ?
C15 C7 C9 C16 0.5(4) . . . . ?
C17 C6 C13 C11 178.9(3) . . . . ?
C17 C10 C14 C12 0.2(4) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 144 electrons were 
found in a volume of 460Å³ in 1 void per unit cell. 
This is consistent with the presence of 
0.3[CHCl3] per Asymmetric Unit 
which account for 139 electrons 
per unit cell.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.471 0.250 115.0 36.2 '0.6 CHCl3'
2 0.000 -0.634 0.750 115.0 36.2 '0.6 CHCl3'
3 0.500 -0.639 0.250 115.0 36.2 '0.6 CHCl3'
4 0.500 -0.875 0.750 115.0 36.2 '0.6 CHCl3'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
