# Electronic Supplementary Material (ESI) for ChemComm.
# 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_murakamilab_hex_autored
_database_code_depnum_ccdc_archive 'CCDC 2343587'
loop_
_audit_author_name
_audit_author_address
'Ryohei Akiyoshi'
;Kwansei Gakuin University
Japan
;
_audit_update_record             
;
2024-03-27 deposited with the CCDC.	2024-05-15 downloaded from the CCDC.
;
_audit_creation_date             2023-10-16
_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         'C13 H8 Br N S'
_chemical_formula_sum            'C13 H8 Br N S'
_chemical_formula_weight         290.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H S N Br'
_chemical_oxdiff_usercomment     '150 K'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   11.7154(2)
_cell_length_b                   14.3463(3)
_cell_length_c                   7.00360(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.820(2)
_cell_angle_gamma                90
_cell_volume                     1147.77(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5302
_cell_measurement_temperature    150
_cell_measurement_theta_max      73.6190
_cell_measurement_theta_min      3.8620
_shelx_estimated_absorpt_T_max   0.743
_shelx_estimated_absorpt_T_min   0.144
_exptl_absorpt_coefficient_mu    6.314
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6034
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.025
_diffrn_reflns_theta_max         67.025
_diffrn_reflns_theta_min         3.870
_diffrn_ambient_temperature      150
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00 -36.00   0.50    0.91    -- -106.00 135.00   4.00   52
  2  ω   -118.00 -72.00   0.50    0.91    -- -106.00 135.00   4.00   92
  3  ω   -112.00 -81.00   0.50    0.91    -- -106.00 125.00 -90.00   62
  4  ω   -116.00 -79.00   0.50    0.91    -- -106.00 134.00-174.00   74
  5  ω    -67.00 -35.00   0.50    0.45    --  -42.33 134.00-174.00   64
  6  ω    -65.00 -40.00   0.50    0.91    -- -106.00   0.00 -60.00   50
  7  ω    -71.00 -37.00   0.50    0.91    -- -106.00  61.00-120.00   68
  8  ω    -67.00 -38.00   0.50    0.91    -- -106.00  61.00-150.00   58
  9  ω    -67.00 -37.00   0.50    0.91    -- -106.00   0.00 -90.00   60
 10  ω    -39.00  34.00   0.50    0.45    --  -42.33  37.00 -30.00  146
 11  ω    -17.00  36.00   0.50    0.45    --  -42.33  19.00  90.00  106
 12  ω    -69.00 -32.00   0.50    0.91    -- -106.00  61.00 150.00   74
 13  ω    -67.00 -33.00   0.50    0.91    -- -106.00  61.00  60.00   68
 14  ω    -65.00 -36.00   0.50    0.91    -- -106.00   0.00-120.00   58
 15  ω    -67.00 -35.00   0.50    0.91    -- -106.00   0.00-180.00   64
 16  ω    -67.00 -42.00   0.50    0.91    -- -106.00   0.00-150.00   50
 17  ω   -147.00-122.00   0.50    0.91    -- -106.00-134.00 117.00   50
 18  ω     37.00  97.00   0.50    0.45    --   42.33-134.00 117.00  120
 19  ω     52.00  77.00   0.50    0.91    --  106.05-134.00 117.00   50
 20  ω     33.00  61.00   0.50    0.91    --  106.05 -94.00 120.00   56
 21  ω     52.00  78.00   0.50    0.91    --  106.05 -94.00 150.00   52
 22  ω     76.00 103.00   0.50    0.91    --  106.05 -94.00 120.00   54
 23  ω     33.00  70.00   0.50    0.91    --  106.05 -61.00 -60.00   74
 24  ω    -37.00  19.00   0.50    0.45    --   42.33 -19.00 -90.00  112
 25  ω     76.00 102.00   0.50    0.45    --   42.33 135.00   4.00   52
 26  ω     68.00 126.00   0.50    0.91    --  106.05 135.00   4.00  116
 27  ω     67.00  92.00   0.50    0.45    --   42.33 134.00-174.00   50
 28  ω     74.00  99.00   0.50    0.91    --  106.05 134.00-174.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0636967000
_diffrn_orient_matrix_UB_12      0.0943801000
_diffrn_orient_matrix_UB_13      0.0383484000
_diffrn_orient_matrix_UB_21      0.1176250000
_diffrn_orient_matrix_UB_22      -0.0512296000
_diffrn_orient_matrix_UB_23      0.0675039000
_diffrn_orient_matrix_UB_31      0.0171884000
_diffrn_orient_matrix_UB_32      0.0007314000
_diffrn_orient_matrix_UB_33      -0.2117806000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1903
_reflns_number_total             2037
_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       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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         0.891
_refine_diff_density_min         -0.832
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2037
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.114
_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)+(0.0737P)²+0.0412P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.0999
_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:
 C4(H4), C7(H7), C9(H9), C2(H2), C8(H8), C6(H6), C12(H12), C3(H3)
;
_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 1.00731(2) 0.40332(2) 0.23339(4) 0.03606(16) Uani 1 1 d . . . . .
S1 S 0.84955(6) 0.67484(5) 0.15899(10) 0.0401(2) Uani 1 1 d . . . . .
N1 N 0.79552(18) 0.51098(14) 0.3242(3) 0.0318(5) Uani 1 1 d . . . . .
C10 C 0.6113(2) 0.39129(15) 0.4656(4) 0.0250(5) Uani 1 1 d . . . . .
C13 C 0.8234(2) 0.57978(18) 0.2527(4) 0.0279(5) Uani 1 1 d . . . . .
C11 C 0.8155(2) 0.42521(17) 0.4151(3) 0.0265(5) Uani 1 1 d . . . . .
C5 C 0.5401(2) 0.35969(15) 0.5927(3) 0.0270(5) Uani 1 1 d . . . . .
C1 C 0.7352(2) 0.39701(14) 0.5417(4) 0.0246(5) Uani 1 1 d . . . . .
C4 C 0.5925(2) 0.33584(16) 0.7887(4) 0.0316(5) Uani 1 1 d . . . . .
H4 H 0.544892 0.314574 0.873270 0.038 Uiso 1 1 calc R U . . .
C7 C 0.3681(2) 0.37207(19) 0.3283(4) 0.0345(6) Uani 1 1 d . . . . .
H7 H 0.285850 0.366445 0.280985 0.041 Uiso 1 1 calc R U . . .
C9 C 0.5574(2) 0.41208(16) 0.2682(4) 0.0281(5) Uani 1 1 d . . . . .
H9 H 0.603933 0.432511 0.181055 0.034 Uiso 1 1 calc R U . . .
C2 C 0.7824(2) 0.37338(18) 0.7330(3) 0.0297(5) Uani 1 1 d . . . . .
H2 H 0.864586 0.377609 0.782007 0.036 Uiso 1 1 calc R U . . .
C8 C 0.4388(3) 0.40288(16) 0.2023(4) 0.0324(6) Uani 1 1 d . . . . .
H8 H 0.403795 0.417473 0.069987 0.039 Uiso 1 1 calc R U . . .
C6 C 0.4178(2) 0.35025(17) 0.5189(4) 0.0318(5) Uani 1 1 d . . . . .
H6 H 0.369840 0.328543 0.602555 0.038 Uiso 1 1 calc R U . . .
C12 C 0.9032(2) 0.37019(18) 0.3903(3) 0.0289(5) Uani 1 1 d . . . . .
H12 H 0.913168 0.311611 0.455108 0.035 Uiso 1 1 calc R U . . .
C3 C 0.7106(2) 0.34298(18) 0.8575(3) 0.0331(5) Uani 1 1 d . . . . .
H3 H 0.744433 0.327414 0.989821 0.040 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 C12 1.875(2) . ?
S1 C13 1.573(3) . ?
N1 C13 1.185(3) . ?
N1 C11 1.381(3) . ?
C10 C5 1.423(3) . ?
C10 C1 1.433(3) . ?
C10 C9 1.418(4) . ?
C11 C1 1.486(3) . ?
C11 C12 1.337(3) . ?
C5 C4 1.416(4) . ?
C5 C6 1.418(3) . ?
C1 C2 1.374(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.363(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.409(4) . ?
C7 C6 1.369(4) . ?
C9 H9 0.9500 . ?
C9 C8 1.370(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.409(3) . ?
C8 H8 0.9500 . ?
C6 H6 0.9500 . ?
C12 H12 0.9500 . ?
C3 H3 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 N1 C11 154.5(2) . . ?
C5 C10 C1 118.2(2) . . ?
C9 C10 C5 118.8(2) . . ?
C9 C10 C1 123.0(2) . . ?
N1 C13 S1 174.9(2) . . ?
N1 C11 C1 116.9(2) . . ?
C12 C11 N1 121.5(2) . . ?
C12 C11 C1 121.6(2) . . ?
C4 C5 C10 119.7(2) . . ?
C4 C5 C6 121.1(2) . . ?
C6 C5 C10 119.2(2) . . ?
C10 C1 C11 121.1(2) . . ?
C2 C1 C10 120.2(2) . . ?
C2 C1 C11 118.6(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 H4 119.6 . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.0(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 C10 120.4(3) . . ?
C8 C9 H9 119.8 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 120.9(2) . . ?
C3 C2 H2 119.5 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.9(3) . . ?
C9 C8 H8 119.6 . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 H6 119.6 . . ?
Br1 C12 H12 118.5 . . ?
C11 C12 Br1 123.0(2) . . ?
C11 C12 H12 118.5 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C11 C1 C10 57.6(3) . . . . ?
N1 C11 C1 C2 -124.5(2) . . . . ?
N1 C11 C12 Br1 0.4(3) . . . . ?
C10 C5 C4 C3 0.2(3) . . . . ?
C10 C5 C6 C7 -0.7(3) . . . . ?
C10 C1 C2 C3 0.2(4) . . . . ?
C10 C9 C8 C7 -0.5(3) . . . . ?
C13 N1 C11 C1 152.6(5) . . . . ?
C13 N1 C11 C12 -27.3(7) . . . . ?
C11 C1 C2 C3 -177.7(2) . . . . ?
C5 C10 C1 C11 177.2(2) . . . . ?
C5 C10 C1 C2 -0.7(3) . . . . ?
C5 C10 C9 C8 0.8(3) . . . . ?
C5 C4 C3 C2 -0.7(4) . . . . ?
C1 C10 C5 C4 0.5(3) . . . . ?
C1 C10 C5 C6 -177.8(2) . . . . ?
C1 C10 C9 C8 178.2(2) . . . . ?
C1 C11 C12 Br1 -179.54(17) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C4 C5 C6 C7 -178.9(2) . . . . ?
C9 C10 C5 C4 178.1(2) . . . . ?
C9 C10 C5 C6 -0.2(3) . . . . ?
C9 C10 C1 C11 -0.3(3) . . . . ?
C9 C10 C1 C2 -178.1(2) . . . . ?
C8 C7 C6 C5 1.0(4) . . . . ?
C6 C5 C4 C3 178.4(2) . . . . ?
C6 C7 C8 C9 -0.5(4) . . . . ?
C12 C11 C1 C10 -122.4(2) . . . . ?
C12 C11 C1 C2 55.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.711
_oxdiff_exptl_absorpt_empirical_full_min 0.519
####################################################################### 
# 
# 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_exp_763_auto
_database_code_depnum_ccdc_archive 'CCDC 2343588'
loop_
_audit_author_name
_audit_author_address
'Ryohei Akiyoshi'
;Kwansei Gakuin University
Japan
;
_audit_update_record             
;
2024-03-27 deposited with the CCDC.	2024-05-15 downloaded from the CCDC.
;
_audit_creation_date             2024-01-11
_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         'C15 H10 Br N S'
_chemical_formula_sum            'C15 H10 Br N S'
_chemical_formula_weight         316.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H Br'
_chemical_oxdiff_usercomment     '150 K'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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'
'-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                   7.4897(2)
_cell_length_b                   18.6819(4)
_cell_length_c                   19.2474(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2693.13(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6829
_cell_measurement_temperature    150
_cell_measurement_theta_max      74.2890
_cell_measurement_theta_min      4.5900
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.292
_exptl_absorpt_coefficient_mu    5.435
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.440
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 1 -6 0.1049
1 12 2 0.1207
-4 2 6 0.0734
-2 -11 1 0.1027
0 2 12 0.0264
4 -4 -5 0.1300
-2 -9 -5 0.0857
-4 2 4 0.0861

_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.01
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.3418 0.5673 -5.5938 0.3006 -0.4396 0.8464
0.6658 11.8532 2.0455 0.5065 -0.7362 -0.4488
-4.2250 1.5869 5.9710 -0.2088 0.3062 -0.9288
-2.3589 -10.5911 0.5018 -0.5657 0.8233 0.0458
0.4446 2.1501 12.2405 0.7841 0.3731 -0.4960
4.1008 -4.0838 -5.2475 0.1674 -0.1013 0.9807
-2.3598 -9.4695 -4.9166 -0.8329 0.5109 0.2127
-4.4676 2.3489 4.3067 -0.3132 0.1908 -0.9303

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9183
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.416
_diffrn_reflns_theta_min         4.595
_diffrn_ambient_temperature      150
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00  64.00   0.50    0.88    --  106.05 -61.00 150.00   56
  2  ω     39.00  65.00   0.50    0.88    --  106.05 -61.00   0.00   52
  3  ω     35.00  60.00   0.50    0.88    --  106.05 -61.00-180.00   50
  4  ω     96.00 178.00   0.50    0.88    --  106.05  57.00-124.00  164
  5  ω     92.00 177.00   0.50    0.88    --  106.05  83.00  99.00  170
  6  ω    -30.00  -3.00   0.50    0.45    --   42.33 -19.00 150.00   54
  7  ω    -31.00  19.00   0.50    0.45    --   42.33 -19.00  30.00  100
  8  ω    -35.00  19.00   0.50    0.45    --   42.33 -19.00 -30.00  108
  9  ω    -28.00  -2.00   0.50    0.45    --   42.33 -19.00-180.00   52
 10  ω     -6.00  29.00   0.50    0.45    --  -42.33  83.00  99.00   70
 11  ω    -73.00 -36.00   0.50    0.88    -- -106.00  61.00  90.00   74
 12  ω    -70.00 -33.00   0.50    0.45    --  -42.33  83.00  99.00   74
 13  ω   -137.00 -61.00   0.50    0.88    -- -106.00  83.00  -9.00  152
 14  ω    -73.00 -37.00   0.50    0.88    -- -106.00  61.00 -60.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1362323000
_diffrn_orient_matrix_UB_12      0.0256573000
_diffrn_orient_matrix_UB_13      0.0546020000
_diffrn_orient_matrix_UB_21      -0.0361607000
_diffrn_orient_matrix_UB_22      -0.0676161000
_diffrn_orient_matrix_UB_23      0.0436703000
_diffrn_orient_matrix_UB_31      0.1498345000
_diffrn_orient_matrix_UB_32      -0.0395472000
_diffrn_orient_matrix_UB_33      -0.0390156000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2413
_reflns_number_total             2673
_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       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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         0.315
_refine_diff_density_min         -0.830
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2673
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      0.977
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1163
_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:
 C14(H14), C7(H7), C10(H10), C11(H11), C12(H12), C4(H4), C3(H3), C13(H13),
 C5(H5), C6(H6)
;
_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 0.24155(3) 0.49397(2) 0.53866(2) 0.03395(15) Uani 1 1 d . . . . .
S1 S 0.55543(9) 0.68321(3) 0.69018(3) 0.0516(2) Uani 1 1 d . . . . .
N1 N 0.4299(2) 0.62975(9) 0.56693(8) 0.0336(4) Uani 1 1 d . . . . .
C8 C 0.3761(2) 0.62687(9) 0.49810(9) 0.0271(4) Uani 1 1 d . . . . .
C2 C 0.2007(2) 0.56179(9) 0.40604(9) 0.0268(3) Uani 1 1 d . . . . .
C1 C 0.2829(2) 0.57034(11) 0.47504(9) 0.0269(4) Uani 1 1 d . . . . .
C9 C 0.4339(2) 0.68864(10) 0.45477(9) 0.0272(4) Uani 1 1 d . . . . .
C14 C 0.4012(3) 0.75813(10) 0.47794(11) 0.0317(4) Uani 1 1 d . . . . .
H14 H 0.340114 0.765729 0.520557 0.038 Uiso 1 1 calc R U . . .
C7 C 0.1070(2) 0.61888(10) 0.37603(10) 0.0331(4) Uani 1 1 d . . . . .
H7 H 0.099233 0.663384 0.399716 0.040 Uiso 1 1 calc R U . . .
C15 C 0.4847(3) 0.65470(10) 0.61824(9) 0.0310(4) Uani 1 1 d . . . . .
C10 C 0.5261(3) 0.67799(9) 0.39291(9) 0.0292(4) Uani 1 1 d . . . . .
H10 H 0.549429 0.630728 0.377126 0.035 Uiso 1 1 calc R U . . .
C11 C 0.5841(3) 0.73611(11) 0.35417(10) 0.0341(4) Uani 1 1 d . . . . .
H11 H 0.647794 0.728628 0.312108 0.041 Uiso 1 1 calc R U . . .
C12 C 0.5489(3) 0.80531(11) 0.37691(11) 0.0365(4) Uani 1 1 d . . . . .
H12 H 0.587270 0.845115 0.350056 0.044 Uiso 1 1 calc R U . . .
C4 C 0.1285(3) 0.48883(11) 0.30634(11) 0.0397(5) Uani 1 1 d . . . . .
H4 H 0.136220 0.444443 0.282442 0.048 Uiso 1 1 calc R U . . .
C3 C 0.2091(4) 0.49690(10) 0.37072(13) 0.0330(5) Uani 1 1 d . . . . .
H3 H 0.270714 0.457658 0.390963 0.040 Uiso 1 1 calc R U . . .
C13 C 0.4581(3) 0.81631(10) 0.43869(11) 0.0351(4) Uani 1 1 d . . . . .
H13 H 0.434629 0.863642 0.454251 0.042 Uiso 1 1 calc R U . . .
C5 C 0.0368(3) 0.54564(13) 0.27698(10) 0.0435(5) Uani 1 1 d . . . . .
H5 H -0.018639 0.540146 0.232905 0.052 Uiso 1 1 calc R U . . .
C6 C 0.0256(3) 0.61053(13) 0.31171(10) 0.0421(5) Uani 1 1 d . . . . .
H6 H -0.037844 0.649312 0.291482 0.051 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 C1 1.9056(19) . ?
S1 C15 1.5753(19) . ?
N1 C8 1.386(2) . ?
N1 C15 1.167(2) . ?
C8 C1 1.342(3) . ?
C8 C9 1.488(3) . ?
C2 C1 1.473(3) . ?
C2 C7 1.401(2) . ?
C2 C3 1.391(3) . ?
C9 C14 1.394(3) . ?
C9 C10 1.391(3) . ?
C14 H14 0.9500 . ?
C14 C13 1.391(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.389(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.386(3) . ?
C4 C5 1.385(3) . ?
C3 H3 0.9500 . ?
C13 H13 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.387(3) . ?
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
C15 N1 C8 157.98(18) . . ?
N1 C8 C9 114.91(15) . . ?
C1 C8 N1 119.87(16) . . ?
C1 C8 C9 125.20(16) . . ?
C7 C2 C1 119.91(16) . . ?
C3 C2 C1 121.09(18) . . ?
C3 C2 C7 118.97(18) . . ?
C8 C1 Br1 117.48(14) . . ?
C8 C1 C2 126.97(17) . . ?
C2 C1 Br1 115.49(14) . . ?
C14 C9 C8 119.44(17) . . ?
C10 C9 C8 120.89(16) . . ?
C10 C9 C14 119.62(18) . . ?
C9 C14 H14 120.0 . . ?
C13 C14 C9 120.01(19) . . ?
C13 C14 H14 120.0 . . ?
C2 C7 H7 119.9 . . ?
C6 C7 C2 120.12(18) . . ?
C6 C7 H7 119.9 . . ?
N1 C15 S1 175.91(17) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.25(18) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 119.96(19) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.08(18) . . ?
C13 C12 H12 120.0 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C5 C4 C3 119.82(19) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 C14 120.06(18) . . ?
C12 C13 H13 120.0 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.20(18) . . ?
C6 C5 H5 119.9 . . ?
C7 C6 H6 120.0 . . ?
C5 C6 C7 120.1(2) . . ?
C5 C6 H6 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C8 C1 Br1 -3.4(2) . . . . ?
N1 C8 C1 C2 173.55(16) . . . . ?
N1 C8 C9 C14 -50.9(2) . . . . ?
N1 C8 C9 C10 126.57(17) . . . . ?
C8 C9 C14 C13 178.58(16) . . . . ?
C8 C9 C10 C11 -177.96(16) . . . . ?
C2 C7 C6 C5 0.0(3) . . . . ?
C1 C8 C9 C14 130.71(19) . . . . ?
C1 C8 C9 C10 -51.8(3) . . . . ?
C1 C2 C7 C6 -178.44(17) . . . . ?
C1 C2 C3 C4 178.8(2) . . . . ?
C9 C8 C1 Br1 174.86(13) . . . . ?
C9 C8 C1 C2 -8.2(3) . . . . ?
C9 C14 C13 C12 -0.7(3) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C14 C9 C10 C11 -0.5(3) . . . . ?
C7 C2 C1 Br1 133.53(15) . . . . ?
C7 C2 C1 C8 -43.5(3) . . . . ?
C7 C2 C3 C4 0.9(3) . . . . ?
C15 N1 C8 C1 -166.4(4) . . . . ?
C15 N1 C8 C9 15.1(6) . . . . ?
C10 C9 C14 C13 1.1(3) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
C3 C2 C1 Br1 -44.3(2) . . . . ?
C3 C2 C1 C8 138.7(2) . . . . ?
C3 C2 C7 C6 -0.6(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C5 C4 C3 C2 -0.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.324
_oxdiff_exptl_absorpt_empirical_full_min 0.491
