# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_hhw_4_auto
_database_code_depnum_ccdc_archive 'CCDC 2305879'
loop_
_audit_author_name
_audit_author_address
'haowen Huang'
;Northwest Normal University
China
;
_audit_update_record             
;
2023-11-06 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;
_audit_creation_date             2023-06-13
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H23 N O2'
_chemical_formula_sum            'C20 H23 N O2'
_chemical_formula_weight         309.39
_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'

_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                   8.0745(4)
_cell_length_b                   10.6294(6)
_cell_length_c                   11.2471(7)
_cell_angle_alpha                102.303(5)
_cell_angle_beta                 109.671(5)
_cell_angle_gamma                103.453(5)
_cell_volume                     838.08(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4385
_cell_measurement_temperature    303.88(10)
_cell_measurement_theta_max      27.4600
_cell_measurement_theta_min      2.0810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.804
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12097
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.694
_diffrn_reflns_theta_min         2.028
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      303.88(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.804
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  64.00   1.00    0.21    --    4.16  68.00 -61.00   79
  2  ω    -17.00  37.00   1.00    0.21    --    4.16 -99.00-120.00   54
  3  ω    -16.00  30.00   1.00    0.21    --    4.16 -99.00 -90.00   46
  4  ω    -16.00  19.00   1.00    0.21    --    4.16 -99.00 120.00   35
  5  ω    -68.00  22.00   1.00    0.21    --    4.16 -68.00 164.00   90
  6  ω    -26.00   5.00   1.00    0.21    --    4.16 -37.00  30.00   31
  7  ω    -57.00  13.00   1.00    0.21    --   -6.19 -77.00  90.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0103147000
_diffrn_orient_matrix_UB_12      0.0675482000
_diffrn_orient_matrix_UB_13      0.0341596000
_diffrn_orient_matrix_UB_21      -0.0370682000
_diffrn_orient_matrix_UB_22      -0.0246236000
_diffrn_orient_matrix_UB_23      0.0427430000
_diffrn_orient_matrix_UB_31      0.0910656000
_diffrn_orient_matrix_UB_32      0.0083221000
_diffrn_orient_matrix_UB_33      0.0446977000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2664
_reflns_number_total             4193
_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 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.051
_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)+(0.0522P)²+0.0555P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1252
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B), C13(H13A,
 H13B), C19(H19A,H19B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C11(H11), C8(H8), C9(H9), C5(H5), C3(H3), C10(H10), C4(H4)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
O1 O 0.15315(14) 0.14725(10) 0.09831(10) 0.0666(3) Uani 1 1 d . . . . .
O2 O -0.13237(13) 0.11533(10) -0.04445(11) 0.0693(3) Uani 1 1 d . . . . .
H2 H -0.136395 0.035452 -0.062208 0.104 Uiso 1 1 calc R U . . .
N1 N 0.98329(14) 0.94744(11) 0.64403(11) 0.0505(3) Uani 1 1 d . . . . .
C7 C 1.26311(17) 0.93020(14) 0.76198(13) 0.0480(3) Uani 1 1 d . . . . .
C1 C 1.10134(18) 1.07803(14) 0.72349(13) 0.0486(3) Uani 1 1 d . . . . .
C12 C 1.07997(17) 0.85702(14) 0.66628(13) 0.0482(3) Uani 1 1 d . . . . .
C20 C 0.03062(18) 0.19265(14) 0.05088(13) 0.0503(3) Uani 1 1 d . . . . .
C6 C 1.27719(17) 1.07160(14) 0.79712(13) 0.0487(3) Uani 1 1 d . . . . .
C14 C 0.64049(17) 0.86648(13) 0.58540(13) 0.0491(3) Uani 1 1 d . . . . .
H14A H 0.633697 0.945928 0.642332 0.059 Uiso 1 1 calc R U . . .
H14B H 0.667671 0.805697 0.636892 0.059 Uiso 1 1 calc R U . . .
C2 C 1.0694(2) 1.20165(15) 0.73309(15) 0.0610(4) Uani 1 1 d . . . . .
H2A H 0.952503 1.205448 0.685743 0.073 Uiso 1 1 calc R U . . .
C11 C 1.0216(2) 0.71677(15) 0.60862(15) 0.0602(4) Uani 1 1 d . . . . .
H11 H 0.901328 0.668734 0.544513 0.072 Uiso 1 1 calc R U . . .
C8 C 1.3869(2) 0.86012(17) 0.80124(15) 0.0605(4) Uani 1 1 d . . . . .
H8 H 1.507920 0.906909 0.864772 0.073 Uiso 1 1 calc R U . . .
C15 C 0.45260(18) 0.79362(13) 0.46603(13) 0.0518(3) Uani 1 1 d . . . . .
H15A H 0.353385 0.791271 0.496644 0.062 Uiso 1 1 calc R U . . .
H15B H 0.439591 0.845431 0.404092 0.062 Uiso 1 1 calc R U . . .
C9 C 1.3281(2) 0.72131(18) 0.74498(17) 0.0695(4) Uani 1 1 d . . . . .
H9 H 1.409760 0.673757 0.771089 0.083 Uiso 1 1 calc R U . . .
C17 C 0.24798(18) 0.57183(13) 0.27321(14) 0.0552(4) Uani 1 1 d . . . . .
H17A H 0.235409 0.620570 0.208661 0.066 Uiso 1 1 calc R U . . .
H17B H 0.145570 0.568537 0.300477 0.066 Uiso 1 1 calc R U . . .
C18 C 0.23560(19) 0.42738(14) 0.20804(14) 0.0572(4) Uani 1 1 d . . . . .
H18A H 0.331274 0.432005 0.173616 0.069 Uiso 1 1 calc R U . . .
H18B H 0.262785 0.382984 0.275818 0.069 Uiso 1 1 calc R U . . .
C13 C 0.79549(17) 0.91049(14) 0.54095(13) 0.0527(3) Uani 1 1 d . . . . .
H13A H 0.779031 0.836853 0.465649 0.063 Uiso 1 1 calc R U . . .
H13B H 0.784731 0.988250 0.510591 0.063 Uiso 1 1 calc R U . . .
C5 C 1.4232(2) 1.19222(16) 0.87832(15) 0.0643(4) Uani 1 1 d . . . . .
H5 H 1.540644 1.189867 0.926541 0.077 Uiso 1 1 calc R U . . .
C19 C 0.04929(19) 0.33959(14) 0.09579(14) 0.0564(4) Uani 1 1 d . . . . .
H19A H -0.049059 0.347761 0.124934 0.068 Uiso 1 1 calc R U . . .
H19B H 0.032248 0.373862 0.020709 0.068 Uiso 1 1 calc R U . . .
C3 C 1.2168(2) 1.31878(16) 0.81519(17) 0.0737(5) Uani 1 1 d . . . . .
H3 H 1.198706 1.402923 0.823158 0.088 Uiso 1 1 calc R U . . .
C10 C 1.1485(2) 0.65087(17) 0.64978(17) 0.0687(4) Uani 1 1 d . . . . .
H10 H 1.112438 0.556742 0.612584 0.082 Uiso 1 1 calc R U . . .
C16 C 0.43064(19) 0.64880(14) 0.39352(14) 0.0584(4) Uani 1 1 d . . . . .
H16A H 0.531840 0.651957 0.364935 0.070 Uiso 1 1 calc R U . . .
H16B H 0.443424 0.597698 0.456086 0.070 Uiso 1 1 calc R U . . .
C4 C 1.3919(2) 1.31389(18) 0.88633(18) 0.0781(5) Uani 1 1 d . . . . .
H4 H 1.489066 1.394682 0.940149 0.094 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
O1 C20 1.2136(16) . ?
O2 C20 1.3146(15) . ?
N1 C1 1.3843(17) . ?
N1 C12 1.3841(16) . ?
N1 C13 1.4639(15) . ?
C7 C12 1.4095(17) . ?
C7 C6 1.437(2) . ?
C7 C8 1.3924(19) . ?
C1 C6 1.4086(18) . ?
C1 C2 1.386(2) . ?
C12 C11 1.386(2) . ?
C20 C19 1.4900(19) . ?
C6 C5 1.3930(19) . ?
C14 C15 1.5306(16) . ?
C14 C13 1.5112(19) . ?
C2 C3 1.378(2) . ?
C11 C10 1.381(2) . ?
C8 C9 1.370(2) . ?
C15 C16 1.5188(19) . ?
C9 C10 1.384(2) . ?
C17 C18 1.518(2) . ?
C17 C16 1.5161(17) . ?
C18 C19 1.5146(18) . ?
C5 C4 1.365(2) . ?
C3 C4 1.390(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C13 126.45(11) . . ?
C12 N1 C1 108.61(11) . . ?
C12 N1 C13 124.52(11) . . ?
C12 C7 C6 106.55(11) . . ?
C8 C7 C12 119.46(13) . . ?
C8 C7 C6 133.99(13) . . ?
N1 C1 C6 108.86(12) . . ?
N1 C1 C2 129.78(13) . . ?
C2 C1 C6 121.32(13) . . ?
N1 C12 C7 109.06(12) . . ?
N1 C12 C11 129.69(13) . . ?
C11 C12 C7 121.24(13) . . ?
O1 C20 O2 122.60(13) . . ?
O1 C20 C19 123.52(12) . . ?
O2 C20 C19 113.88(11) . . ?
C1 C6 C7 106.91(11) . . ?
C5 C6 C7 133.73(13) . . ?
C5 C6 C1 119.27(14) . . ?
C13 C14 C15 111.23(11) . . ?
C3 C2 C1 117.75(14) . . ?
C10 C11 C12 117.62(14) . . ?
C9 C8 C7 119.09(14) . . ?
C16 C15 C14 113.03(11) . . ?
C8 C9 C10 120.87(14) . . ?
C16 C17 C18 112.20(11) . . ?
C19 C18 C17 115.15(12) . . ?
N1 C13 C14 114.45(11) . . ?
C4 C5 C6 119.25(14) . . ?
C20 C19 C18 113.57(11) . . ?
C2 C3 C4 121.45(16) . . ?
C11 C10 C9 121.71(15) . . ?
C17 C16 C15 115.48(11) . . ?
C5 C4 C3 120.94(15) . . ?

_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 1.152
_oxdiff_exptl_absorpt_empirical_full_min 0.753
####################################################################### 
# 
# 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_hhw_1_auto
_database_code_depnum_ccdc_archive 'CCDC 2305881'
loop_
_audit_author_name
_audit_author_address
'haowen Huang'
;Northwest Normal University
China
;
_audit_update_record             
;
2023-11-06 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;
_audit_creation_date             2023-05-27
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H24 Br N'
_chemical_formula_sum            'C20 H24 Br N'
_chemical_formula_weight         358.31
_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 0.0181 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'

_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                   16.3774(3)
_cell_length_b                   7.78421(13)
_cell_length_c                   27.7655(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3539.68(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9022
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      76.2310
_cell_measurement_theta_min      3.1190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.77a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1488
_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  0.0289
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            12438
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.428
_diffrn_reflns_theta_min         3.183
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.954
_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  88.00   0.50    0.05    --   46.28-125.00 -30.00   52
  2  ω     37.00 107.00   0.50    0.05    --  104.28-118.00  10.00  140
  3  ω     34.00  64.00   0.50    0.05    --  104.28 -61.00  60.00   60
  4  ω     64.00  89.00   0.50    0.05    --   46.28 157.00-108.00   50
  5  ω     86.00 169.00   0.50    0.05    --  104.28 137.00  -4.00  166
  6  ω    -24.00  29.00   0.50    0.05    --   46.28 -19.00  30.00  106
  7  ω   -165.00 -85.00   0.50    0.05    -- -102.00 -10.00 155.00  160
  8  ω    -21.00  29.00   0.50    0.05    --  -46.28  19.00  30.00  100
  9  ω    -24.00  10.00   0.50    0.05    --  -46.28  19.00 -60.00   68
 10  ω    -61.00 -30.00   0.50    0.05    -- -102.00  61.00  30.00   62
 11  ω   -111.00 -72.00   0.50    0.05    -- -102.00 125.00  60.00   78
 12  ω    -63.00 -37.00   0.50    0.05    -- -102.00 125.00  60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0552378000
_diffrn_orient_matrix_UB_12      -0.0117760000
_diffrn_orient_matrix_UB_13      -0.0447806000
_diffrn_orient_matrix_UB_21      0.0751073000
_diffrn_orient_matrix_UB_22      -0.0232614000
_diffrn_orient_matrix_UB_23      0.0327274000
_diffrn_orient_matrix_UB_31      -0.0122399000
_diffrn_orient_matrix_UB_32      -0.1962652000
_diffrn_orient_matrix_UB_33      -0.0011410000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3096
_reflns_number_total             3539
_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 1.171.42.77a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.77a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.77a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.00042(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3539
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.082
_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)+(0.0429P)²+1.4282P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0937
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,
 H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11)
;
_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 0.64593(2) -0.45479(3) 0.46117(2) 0.06541(14) Uani 1 1 d . . . . .
N1 N 0.56546(9) 0.79634(19) 0.65887(5) 0.0368(3) Uani 1 1 d . . . . .
C1 C 0.48930(12) 0.8646(2) 0.64822(7) 0.0385(4) Uani 1 1 d . . . . .
C2 C 0.43274(13) 0.8111(3) 0.61410(7) 0.0482(5) Uani 1 1 d . . . . .
H2 H 0.443173 0.714868 0.593965 0.058 Uiso 1 1 calc R U . . .
C3 C 0.36055(14) 0.9030(4) 0.61049(9) 0.0598(6) Uani 1 1 d . . . . .
H3 H 0.320672 0.868777 0.587573 0.072 Uiso 1 1 calc R U . . .
C4 C 0.34531(15) 1.0445(4) 0.63974(9) 0.0614(7) Uani 1 1 d . . . . .
H4 H 0.295433 1.105481 0.636196 0.074 Uiso 1 1 calc R U . . .
C5 C 0.40145(14) 1.0983(3) 0.67401(8) 0.0516(5) Uani 1 1 d . . . . .
H5 H 0.390576 1.195194 0.693817 0.062 Uiso 1 1 calc R U . . .
C6 C 0.47456(12) 1.0063(3) 0.67865(7) 0.0393(4) Uani 1 1 d . . . . .
C7 C 0.54506(12) 1.0231(2) 0.70938(7) 0.0372(4) Uani 1 1 d . . . . .
C8 C 0.56666(13) 1.1346(2) 0.74653(7) 0.0438(5) Uani 1 1 d . . . . .
H8 H 0.530307 1.223066 0.756337 0.053 Uiso 1 1 calc R U . . .
C9 C 0.64114(13) 1.1155(3) 0.76888(8) 0.0481(5) Uani 1 1 d . . . . .
H9 H 0.656177 1.191435 0.794167 0.058 Uiso 1 1 calc R U . . .
C10 C 0.69484(13) 0.9854(3) 0.75469(7) 0.0461(5) Uani 1 1 d . . . . .
H10 H 0.746131 0.975354 0.770417 0.055 Uiso 1 1 calc R U . . .
C11 C 0.67529(12) 0.8707(2) 0.71830(7) 0.0404(4) Uani 1 1 d . . . . .
H11 H 0.711837 0.781965 0.709013 0.048 Uiso 1 1 calc R U . . .
C12 C 0.59977(11) 0.8911(2) 0.69592(6) 0.0347(4) Uani 1 1 d . . . . .
C13 C 0.60431(12) 0.6505(2) 0.63515(7) 0.0388(4) Uani 1 1 d . . . . .
H13A H 0.662354 0.678997 0.629175 0.047 Uiso 1 1 calc R U . . .
H13B H 0.577886 0.632575 0.603475 0.047 Uiso 1 1 calc R U . . .
C14 C 0.60019(13) 0.4840(2) 0.66351(6) 0.0382(4) Uani 1 1 d . . . . .
H14A H 0.542364 0.449739 0.667502 0.046 Uiso 1 1 calc R U . . .
H14B H 0.623623 0.502498 0.695965 0.046 Uiso 1 1 calc R U . . .
C15 C 0.64672(11) 0.3395(2) 0.63835(7) 0.0365(4) Uani 1 1 d . . . . .
H15A H 0.700983 0.383348 0.628576 0.044 Uiso 1 1 calc R U . . .
H15B H 0.655697 0.245331 0.661732 0.044 Uiso 1 1 calc R U . . .
C16 C 0.60410(11) 0.2659(2) 0.59401(6) 0.0365(4) Uani 1 1 d . . . . .
H16A H 0.548069 0.230179 0.602900 0.044 Uiso 1 1 calc R U . . .
H16B H 0.599732 0.356509 0.569136 0.044 Uiso 1 1 calc R U . . .
C17 C 0.64952(11) 0.1125(3) 0.57309(7) 0.0367(4) Uani 1 1 d . . . . .
H17A H 0.661037 0.029700 0.599287 0.044 Uiso 1 1 calc R U . . .
H17B H 0.702541 0.152174 0.560073 0.044 Uiso 1 1 calc R U . . .
C18 C 0.60261(12) 0.0204(2) 0.53321(6) 0.0364(4) Uani 1 1 d . . . . .
H18A H 0.594047 0.100928 0.506075 0.044 Uiso 1 1 calc R U . . .
H18B H 0.548258 -0.013512 0.545584 0.044 Uiso 1 1 calc R U . . .
C19 C 0.64680(11) -0.1394(2) 0.51465(7) 0.0370(4) Uani 1 1 d . . . . .
H19A H 0.696883 -0.104328 0.497269 0.044 Uiso 1 1 calc R U . . .
H19B H 0.663256 -0.211989 0.542268 0.044 Uiso 1 1 calc R U . . .
C20 C 0.59292(12) -0.2417(3) 0.48140(8) 0.0436(4) Uani 1 1 d . . . . .
H20A H 0.579785 -0.171793 0.452641 0.052 Uiso 1 1 calc R U . . .
H20B H 0.541078 -0.269228 0.498030 0.052 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 C20 1.9545(19) . ?
N1 C1 1.388(2) . ?
N1 C12 1.385(2) . ?
N1 C13 1.458(2) . ?
C1 C2 1.389(3) . ?
C1 C6 1.410(3) . ?
C2 C3 1.386(3) . ?
C3 C4 1.391(4) . ?
C4 C5 1.388(4) . ?
C5 C6 1.401(3) . ?
C6 C7 1.442(3) . ?
C7 C8 1.394(3) . ?
C7 C12 1.414(3) . ?
C8 C9 1.377(3) . ?
C9 C10 1.398(3) . ?
C10 C11 1.386(3) . ?
C11 C12 1.393(3) . ?
C13 C14 1.519(3) . ?
C14 C15 1.528(3) . ?
C15 C16 1.527(3) . ?
C16 C17 1.522(3) . ?
C17 C18 1.527(3) . ?
C18 C19 1.528(3) . ?
C19 C20 1.505(3) . ?

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
C1 N1 C13 126.44(16) . . ?
C12 N1 C1 108.60(15) . . ?
C12 N1 C13 124.96(16) . . ?
N1 C1 C2 129.03(19) . . ?
N1 C1 C6 109.01(17) . . ?
C2 C1 C6 121.96(19) . . ?
C3 C2 C1 117.6(2) . . ?
C2 C3 C4 121.3(2) . . ?
C5 C4 C3 121.4(2) . . ?
C4 C5 C6 118.3(2) . . ?
C1 C6 C7 106.77(17) . . ?
C5 C6 C1 119.4(2) . . ?
C5 C6 C7 133.8(2) . . ?
C8 C7 C6 134.25(18) . . ?
C8 C7 C12 119.17(19) . . ?
C12 C7 C6 106.57(16) . . ?
C9 C8 C7 119.43(19) . . ?
C8 C9 C10 120.56(19) . . ?
C11 C10 C9 121.8(2) . . ?
C10 C11 C12 117.20(18) . . ?
N1 C12 C7 109.04(17) . . ?
N1 C12 C11 129.12(17) . . ?
C11 C12 C7 121.84(17) . . ?
N1 C13 C14 114.25(15) . . ?
C13 C14 C15 111.67(15) . . ?
C16 C15 C14 114.65(15) . . ?
C17 C16 C15 112.26(15) . . ?
C16 C17 C18 113.54(15) . . ?
C17 C18 C19 112.85(15) . . ?
C20 C19 C18 111.09(15) . . ?
C19 C20 Br1 111.41(13) . . ?

_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 1.448
_oxdiff_exptl_absorpt_empirical_full_min 0.764
####################################################################### 
# 
# 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_hhw-5_auto
_database_code_depnum_ccdc_archive 'CCDC 2305882'
loop_
_audit_author_name
_audit_author_address
'haowen Huang'
;Northwest Normal University
China
;
_audit_update_record             
;
2023-11-06 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;
_audit_creation_date             2023-07-17
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C21 H28 N3 S'
_chemical_formula_sum            'C21 H28 Br N3 S'
_chemical_formula_weight         434.43
_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 0.0181 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                   13.77310(10)
_cell_length_b                   9.33470(10)
_cell_length_c                   16.8784(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.8350(10)
_cell_angle_gamma                90
_cell_volume                     2144.27(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10829
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      75.4410
_cell_measurement_theta_min      2.6580
_shelx_estimated_absorpt_T_max   0.788
_shelx_estimated_absorpt_T_min   0.653
_exptl_absorpt_coefficient_mu    3.581
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.13
_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  0.0238
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13957
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.766
_diffrn_reflns_theta_min         3.247
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     40.00  68.00   0.50    0.05    --  104.21 -61.00 150.00   56
  2  ω     37.00  73.00   0.50    0.05    --  104.21 -61.00 120.00   72
  3  ω     37.00  71.00   0.50    0.05    --  104.21 -61.00  90.00   68
  4  ω    -25.00  29.00   0.50    0.05    --   46.61 -19.00 -60.00  108
  5  ω     38.00  70.00   0.50    0.05    --  104.21 -61.00 -60.00   64
  6  ω     34.00  63.00   0.50    0.05    --  104.21 -61.00 -90.00   58
  7  ω    145.00 176.00   0.50    0.05    --  104.21  15.00 -30.00   62
  8  ω    127.00 153.00   0.50    0.05    --  104.21 103.00-125.00   52
  9  ω     99.00 140.00   0.50    0.05    --  104.21  15.00 -30.00   82
 10  ω     60.00 107.00   0.50    0.05    --  104.21-103.00 131.00   94
 11  ω     17.00  42.00   0.50    0.05    --   46.61-103.00 131.00   50
 12  ω    -24.00  15.00   0.50    0.05    --  -46.61  19.00 150.00   78
 13  ω    -69.00 -29.00   0.50    0.05    -- -102.00  61.00  60.00   80
 14  ω    -79.00 -30.00   0.50    0.05    -- -102.00  77.00   0.00   98
 15  ω    -81.00 -29.00   0.50    0.05    -- -102.00  77.00-120.00  104
 16  ω   -106.00 -52.00   0.50    0.05    -- -102.00 103.00-125.00  108
 17  ω    -77.00  -5.00   0.50    0.05    --  -46.61 103.00-125.00  144
 18  ω    -91.00 -65.00   0.50    0.05    -- -102.00 125.00 150.00   52
 19  ω    -60.00 -33.00   0.50    0.05    -- -102.00 125.00 150.00   54
 20  ω   -175.00 -91.00   0.50    0.05    -- -102.00 -30.00 120.00  168
 21  ω   -151.00-103.00   0.50    0.05    -- -102.00-103.00 131.00   96
 22  ω   -116.00 -33.00   0.50    0.05    --  -46.61 -57.00 120.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0319940000
_diffrn_orient_matrix_UB_12      -0.1578602000
_diffrn_orient_matrix_UB_13      0.0104350000
_diffrn_orient_matrix_UB_21      -0.0439705000
_diffrn_orient_matrix_UB_22      -0.0077172000
_diffrn_orient_matrix_UB_23      0.0785091000
_diffrn_orient_matrix_UB_31      -0.0992998000
_diffrn_orient_matrix_UB_32      -0.0473032000
_diffrn_orient_matrix_UB_33      -0.0475705000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3954
_reflns_number_total             4286
_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 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      0.963
_refine_ls_shift/su_max          0.003
_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          0.1104
_refine_ls_wR_factor_ref         0.1139
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,
 H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11)
2.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N3(H3A,H3B)
;
_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 1.04349(2) 1.18920(2) 0.61839(2) 0.03562(12) Uani 1 1 d . . . . .
S1 S 0.89609(3) 0.63498(5) 0.65379(3) 0.03248(14) Uani 1 1 d . . . . .
N1 N 0.49576(10) 0.00727(16) 0.18372(9) 0.0273(3) Uani 1 1 d . . . . .
N2 N 0.96751(12) 0.85812(17) 0.57913(9) 0.0338(3) Uani 1 1 d . . . . .
H2A H 0.995157 0.943058 0.578813 0.041 Uiso 1 1 calc R U . . .
H2B H 0.947849 0.813143 0.533674 0.041 Uiso 1 1 calc R U . . .
N3 N 0.98478(11) 0.86521(17) 0.71525(9) 0.0332(3) Uani 1 1 d . . . . .
H3A H 1.012461 0.950165 0.715161 0.040 Uiso 1 1 calc R U . . .
H3B H 0.976662 0.824911 0.760905 0.040 Uiso 1 1 calc R U . . .
C1 C 0.42537(12) -0.00074(18) 0.23419(10) 0.0268(3) Uani 1 1 d . . . . .
C2 C 0.42779(13) -0.07595(19) 0.30577(11) 0.0303(4) Uani 1 1 d . . . . .
H2 H 0.483559 -0.130948 0.327617 0.036 Uiso 1 1 calc R U . . .
C3 C 0.34602(14) -0.0675(2) 0.34372(11) 0.0342(4) Uani 1 1 d . . . . .
H3 H 0.345521 -0.118656 0.392308 0.041 Uiso 1 1 calc R U . . .
C4 C 0.26381(13) 0.0145(2) 0.31255(11) 0.0362(4) Uani 1 1 d . . . . .
H4 H 0.208580 0.017188 0.340006 0.043 Uiso 1 1 calc R U . . .
C5 C 0.26193(13) 0.0915(2) 0.24239(11) 0.0324(4) Uani 1 1 d . . . . .
H5 H 0.206313 0.147713 0.221674 0.039 Uiso 1 1 calc R U . . .
C6 C 0.34360(12) 0.08478(18) 0.20258(10) 0.0268(3) Uani 1 1 d . . . . .
C7 C 0.36780(12) 0.15009(19) 0.13025(10) 0.0272(3) Uani 1 1 d . . . . .
C8 C 0.31932(14) 0.2478(2) 0.07475(11) 0.0335(4) Uani 1 1 d . . . . .
H8 H 0.256000 0.283083 0.080224 0.040 Uiso 1 1 calc R U . . .
C9 C 0.36575(16) 0.2917(2) 0.01174(13) 0.0384(5) Uani 1 1 d . . . . .
H9 H 0.333598 0.357235 -0.026655 0.046 Uiso 1 1 calc R U . . .
C10 C 0.45938(15) 0.2409(2) 0.00381(11) 0.0369(4) Uani 1 1 d . . . . .
H10 H 0.489751 0.273741 -0.039682 0.044 Uiso 1 1 calc R U . . .
C11 C 0.50898(14) 0.1440(2) 0.05759(11) 0.0322(4) Uani 1 1 d . . . . .
H11 H 0.572280 0.109396 0.051509 0.039 Uiso 1 1 calc R U . . .
C12 C 0.46227(12) 0.09915(18) 0.12113(10) 0.0273(3) Uani 1 1 d . . . . .
C13 C 0.59231(12) -0.0600(2) 0.19812(11) 0.0316(4) Uani 1 1 d . . . . .
H13A H 0.608891 -0.094664 0.146402 0.038 Uiso 1 1 calc R U . . .
H13B H 0.589312 -0.144404 0.233183 0.038 Uiso 1 1 calc R U . . .
C14 C 0.67408(12) 0.0392(2) 0.23695(10) 0.0306(4) Uani 1 1 d . . . . .
H14A H 0.736348 -0.015534 0.246152 0.037 Uiso 1 1 calc R U . . .
H14B H 0.682171 0.117459 0.198906 0.037 Uiso 1 1 calc R U . . .
C15 C 0.65698(12) 0.10547(19) 0.31630(10) 0.0276(3) Uani 1 1 d . . . . .
H15A H 0.647677 0.028229 0.354627 0.033 Uiso 1 1 calc R U . . .
H15B H 0.596275 0.163870 0.307448 0.033 Uiso 1 1 calc R U . . .
C16 C 0.74339(13) 0.19967(19) 0.35218(12) 0.0306(4) Uani 1 1 d . . . . .
H16A H 0.803575 0.140171 0.361234 0.037 Uiso 1 1 calc R U . . .
H16B H 0.753279 0.274846 0.312823 0.037 Uiso 1 1 calc R U . . .
C17 C 0.73017(13) 0.2714(2) 0.43092(11) 0.0302(4) Uani 1 1 d . . . . .
H17A H 0.726336 0.197059 0.472181 0.036 Uiso 1 1 calc R U . . .
H17B H 0.667723 0.325739 0.423474 0.036 Uiso 1 1 calc R U . . .
C18 C 0.81530(12) 0.3728(2) 0.45965(11) 0.0309(4) Uani 1 1 d . . . . .
H18A H 0.817002 0.448188 0.418652 0.037 Uiso 1 1 calc R U . . .
H18B H 0.877548 0.318280 0.463788 0.037 Uiso 1 1 calc R U . . .
C19 C 0.81053(12) 0.44477(19) 0.54026(11) 0.0303(4) Uani 1 1 d . . . . .
H19A H 0.744559 0.486825 0.540338 0.036 Uiso 1 1 calc R U . . .
H19B H 0.822461 0.373125 0.583917 0.036 Uiso 1 1 calc R U . . .
C20 C 0.88806(13) 0.5613(2) 0.55368(11) 0.0338(4) Uani 1 1 d . . . . .
H20A H 0.871236 0.638432 0.513678 0.041 Uiso 1 1 calc R U . . .
H20B H 0.952569 0.521065 0.546281 0.041 Uiso 1 1 calc R U . . .
C21 C 0.95560(12) 0.79862(18) 0.64728(11) 0.0276(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
S1 C20 1.8119(18) . ?
S1 C21 1.7449(18) . ?
N1 C1 1.387(2) . ?
N1 C12 1.384(2) . ?
N1 C13 1.457(2) . ?
N2 C21 1.310(2) . ?
N3 C21 1.312(2) . ?
C1 C2 1.393(3) . ?
C1 C6 1.416(2) . ?
C2 C3 1.381(3) . ?
C3 C4 1.400(3) . ?
C4 C5 1.382(3) . ?
C5 C6 1.397(2) . ?
C6 C7 1.448(2) . ?
C7 C8 1.401(3) . ?
C7 C12 1.416(2) . ?
C8 C9 1.384(3) . ?
C9 C10 1.400(3) . ?
C10 C11 1.385(3) . ?
C11 C12 1.397(2) . ?
C13 C14 1.526(2) . ?
C14 C15 1.526(2) . ?
C15 C16 1.528(2) . ?
C16 C17 1.524(3) . ?
C17 C18 1.527(2) . ?
C18 C19 1.528(2) . ?
C19 C20 1.517(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 S1 C20 103.63(9) . . ?
C1 N1 C13 125.47(15) . . ?
C12 N1 C1 108.65(13) . . ?
C12 N1 C13 125.68(15) . . ?
N1 C1 C2 129.32(16) . . ?
N1 C1 C6 109.18(15) . . ?
C2 C1 C6 121.50(16) . . ?
C3 C2 C1 117.44(16) . . ?
C2 C3 C4 121.80(16) . . ?
C5 C4 C3 120.91(17) . . ?
C4 C5 C6 118.57(16) . . ?
C1 C6 C7 106.39(14) . . ?
C5 C6 C1 119.75(16) . . ?
C5 C6 C7 133.85(16) . . ?
C8 C7 C6 133.62(17) . . ?
C8 C7 C12 119.83(17) . . ?
C12 C7 C6 106.53(15) . . ?
C9 C8 C7 118.51(18) . . ?
C8 C9 C10 120.94(19) . . ?
C11 C10 C9 121.84(18) . . ?
C10 C11 C12 117.38(17) . . ?
N1 C12 C7 109.23(15) . . ?
N1 C12 C11 129.28(16) . . ?
C11 C12 C7 121.48(17) . . ?
N1 C13 C14 113.86(14) . . ?
C15 C14 C13 114.81(14) . . ?
C14 C15 C16 111.42(14) . . ?
C17 C16 C15 114.10(15) . . ?
C16 C17 C18 111.13(15) . . ?
C17 C18 C19 114.81(14) . . ?
C20 C19 C18 108.84(14) . . ?
C19 C20 S1 110.63(12) . . ?
N2 C21 S1 123.35(14) . . ?
N2 C21 N3 120.25(16) . . ?
N3 C21 S1 116.31(14) . . ?

_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 1.268
_oxdiff_exptl_absorpt_empirical_full_min 0.839
