# Supplementary Information (SI) for Materials Horizons.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_s_alfa_4_br_ba_cl_390k_auto
_database_code_depnum_ccdc_archive 'CCDC 2516741'
loop_
_audit_author_name
_audit_author_address
'Xiaogang chen'
;Nanchang University
China
;
_audit_update_record             
;
2025-12-17 deposited with the CCDC.	2026-03-31 downloaded from the CCDC.
;
_audit_creation_date             2025-11-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H11 Br N, Cl'
_chemical_formula_sum            'C8 H11 Br Cl N'
_chemical_formula_weight         236.54
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S '
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'
Cl Cl 0.3639 0.7018 '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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.5054(4)
_cell_length_b                   7.0895(5)
_cell_length_c                   13.1417(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.486(7)
_cell_angle_gamma                90
_cell_volume                     511.36(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1949
_cell_measurement_temperature    390.00(10)
_cell_measurement_theta_max      71.0160
_cell_measurement_theta_min      3.3630
_shelx_estimated_absorpt_T_max   0.525
_shelx_estimated_absorpt_T_min   0.403
_exptl_absorpt_coefficient_mu    7.408
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.129a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2716
_diffrn_reflns_point_group_measured_fraction_full 0.774
_diffrn_reflns_point_group_measured_fraction_max 0.748
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.415
_diffrn_reflns_theta_min         3.373
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      390.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.993
_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     52.00  78.00   0.50    0.05    --   60.32  15.00 -30.00   52
  2  ω     53.00 104.00   0.50    0.05    --   60.32  15.00  90.00  102
  3  ω     58.00 108.00   0.50    0.05    --   74.97  15.00  60.00  100
  4  ω     53.00  99.00   0.50    0.05    --   60.32  15.00-180.00   92
  5  ω     24.00  76.00   0.50    0.05    --   60.32-125.00  30.00  104
  6  ω     44.00  84.00   0.50    0.05    --   60.32-125.00-120.00   80
  7  ω     51.00  99.00   0.50    0.05    --   74.97-125.00-150.00   96
  8  ω     64.00  92.00   0.50    0.05    --   74.97-125.00-120.00   56
  9  ω     35.00  97.00   0.50    0.05    --   74.97-125.00 120.00  124
 10  ω   -121.00 -59.00   0.50    0.05    --  -75.57 -15.00 120.00  124
 11  ω   -115.00 -58.00   0.50    0.05    --  -74.06 -15.00-120.00  114
 12  ω   -119.00 -93.00   0.50    0.05    --  -74.06 -15.00-180.00   52
 13  ω    -81.00 -56.00   0.50    0.05    --  -74.06 -15.00-180.00   50
 14  ω    -78.00 -36.00   0.50    0.05    --  -60.72 125.00-150.00   84
 15  ω    -89.00 -54.00   0.50    0.05    --  -75.57 125.00-120.00   70
 16  ω    -46.00 -20.00   0.50    0.05    --  -60.72 125.00  30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1904871000
_diffrn_orient_matrix_UB_12      0.0633287000
_diffrn_orient_matrix_UB_13      0.0728704000
_diffrn_orient_matrix_UB_21      -0.1914313000
_diffrn_orient_matrix_UB_22      0.0193398000
_diffrn_orient_matrix_UB_23      -0.0912574000
_diffrn_orient_matrix_UB_31      -0.0760830000
_diffrn_orient_matrix_UB_32      -0.2070015000
_diffrn_orient_matrix_UB_33      0.0139010000
_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         0.420
_reflns_Friedel_fraction_full    0.512
_reflns_Friedel_fraction_max     0.484
_reflns_number_gt                1288
_reflns_number_total             1481
_reflns_odcompleteness_completeness 99.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.129a 64-bit (release 29-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.910
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.114
_refine_ls_abs_structure_details 
;
 Flack x determined using 332 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1481
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0692
_refine_ls_restrained_S_all      1.073
_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)+(0.1435P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1934
_refine_ls_wR_factor_ref         0.2008
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C1(H1D,H1E,H1F)
;
_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
Br1 Br 0.9616(3) 0.9142(2) 0.92824(12) 0.1219(7) Uani 1 1 d . . . . .
Cl1 Cl 0.1890(4) 0.7446(4) 0.5251(2) 0.0905(8) Uani 1 1 d . . . . .
N1 N 0.3266(13) 0.3288(14) 0.5833(6) 0.080(2) Uani 1 1 d . . . . .
H1A H 0.307845 0.450771 0.568682 0.120 Uiso 1 1 calc R U . . .
H1B H 0.197220 0.265094 0.557139 0.120 Uiso 1 1 calc R U . . .
H1C H 0.459790 0.285815 0.556787 0.120 Uiso 1 1 calc R U . . .
C1 C 0.457(4) 0.105(2) 0.7175(13) 0.125(5) Uani 1 1 d . . . . .
H1D H 0.584558 0.078814 0.673636 0.188 Uiso 1 1 calc R U . . .
H1E H 0.330645 0.012585 0.706646 0.188 Uiso 1 1 calc R U . . .
H1F H 0.522435 0.100784 0.787430 0.188 Uiso 1 1 calc R U . . .
C2 C 0.3512(18) 0.3041(15) 0.6932(9) 0.082(2) Uani 1 1 d . . . . .
H2 H 0.187540 0.308710 0.717484 0.098 Uiso 1 1 calc R U . . .
C3 C 0.5007(14) 0.4540(14) 0.7480(7) 0.071(2) Uani 1 1 d . . . . .
C4 C 0.7017(16) 0.5408(16) 0.7059(6) 0.073(2) Uani 1 1 d . . . . .
H4 H 0.742148 0.505724 0.641182 0.087 Uiso 1 1 calc R U . . .
C5 C 0.8375(16) 0.6755(17) 0.7590(7) 0.080(2) Uani 1 1 d . . . . .
H5 H 0.969379 0.731113 0.730478 0.096 Uiso 1 1 calc R U . . .
C6 C 0.7782(17) 0.7280(17) 0.8542(7) 0.082(2) Uani 1 1 d . . . . .
C7 C 0.5829(19) 0.653(2) 0.8970(8) 0.092(3) Uani 1 1 d . . . . .
H7 H 0.542836 0.693288 0.960980 0.111 Uiso 1 1 calc R U . . .
C8 C 0.442(2) 0.5148(18) 0.8431(8) 0.085(3) Uani 1 1 d . . . . .
H8 H 0.307724 0.463373 0.871727 0.102 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 C6 1.885(11) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C2 1.449(14) . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C1 H1F 0.9600 . ?
C1 C2 1.551(18) . ?
C2 H2 0.9800 . ?
C2 C3 1.495(15) . ?
C3 C4 1.416(13) . ?
C3 C8 1.382(14) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(14) . ?
C5 H5 0.9300 . ?
C5 C6 1.370(13) . ?
C6 C7 1.359(16) . ?
C7 H7 0.9300 . ?
C7 C8 1.409(18) . ?
C8 H8 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
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
N1 C2 C1 108.7(11) . . ?
N1 C2 H2 107.7 . . ?
N1 C2 C3 113.5(8) . . ?
C1 C2 H2 107.7 . . ?
C3 C2 C1 111.3(9) . . ?
C3 C2 H2 107.7 . . ?
C4 C3 C2 122.5(9) . . ?
C8 C3 C2 119.9(9) . . ?
C8 C3 C4 117.6(9) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.1(9) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.7(9) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 Br1 120.3(8) . . ?
C7 C6 Br1 117.9(8) . . ?
C7 C6 C5 121.7(10) . . ?
C6 C7 H7 120.5 . . ?
C6 C7 C8 119.1(9) . . ?
C8 C7 H7 120.5 . . ?
C3 C8 C7 120.9(9) . . ?
C3 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A Cl1 0.89 2.24 3.124(10) 169.6 . yes
N1 H1B Cl1 0.89 2.31 3.133(7) 153.1 2_546 yes
N1 H1C Cl1 0.89 2.30 3.177(8) 166.8 2_646 yes

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 C6 C7 C8 179.7(9) . . . . ?
N1 C2 C3 C4 -33.9(13) . . . . ?
N1 C2 C3 C8 145.1(9) . . . . ?
C1 C2 C3 C4 89.1(14) . . . . ?
C1 C2 C3 C8 -91.9(13) . . . . ?
C2 C3 C4 C5 -178.9(9) . . . . ?
C2 C3 C8 C7 178.8(11) . . . . ?
C3 C4 C5 C6 -0.2(16) . . . . ?
C4 C3 C8 C7 -2.1(16) . . . . ?
C4 C5 C6 Br1 -179.6(8) . . . . ?
C4 C5 C6 C7 -1.8(18) . . . . ?
C5 C6 C7 C8 1.8(19) . . . . ?
C6 C7 C8 C3 0.2(19) . . . . ?
C8 C3 C4 C5 2.1(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 3.137
_oxdiff_exptl_absorpt_empirical_full_min 0.380
####################################################################### 
# 
# 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_s_alfa_4_br_ba_cl_300k_auto
_database_code_depnum_ccdc_archive 'CCDC 2516744'
loop_
_audit_author_name
_audit_author_address
'Xiaogang chen'
;Nanchang University
China
;
_audit_update_record             
;
2025-12-17 deposited with the CCDC.	2026-03-31 downloaded from the CCDC.
;
_audit_creation_date             2025-11-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H11 Br N, Cl'
_chemical_formula_sum            'C8 H11 Br Cl N'
_chemical_formula_weight         236.54
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N Cl Br  '
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'
Cl Cl 0.3639 0.7018 '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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.4758(2)
_cell_length_b                   7.0246(2)
_cell_length_c                   13.0918(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.062(3)
_cell_angle_gamma                90
_cell_volume                     502.32(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2248
_cell_measurement_temperature    299.81(17)
_cell_measurement_theta_max      71.1110
_cell_measurement_theta_min      3.3670
_shelx_estimated_absorpt_T_max   0.519
_shelx_estimated_absorpt_T_min   0.398
_exptl_absorpt_coefficient_mu    7.541
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.06909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.129a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2860
_diffrn_reflns_point_group_measured_fraction_full 0.792
_diffrn_reflns_point_group_measured_fraction_max 0.768
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.638
_diffrn_reflns_theta_min         3.384
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.81(17)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     51.00 103.00   0.50    0.05    --   60.32  15.00  30.00  104
  2  ω     48.00 100.00   0.50    0.05    --   60.32  15.00 -30.00  104
  3  ω     54.00  89.00   0.50    0.05    --   60.32  15.00 -60.00   70
  4  ω     74.00 109.00   0.50    0.05    --   74.97  15.00-120.00   70
  5  ω     43.00  70.00   0.50    0.05    --   60.32-125.00 -30.00   54
  6  ω     71.00  99.00   0.50    0.05    --   74.97-125.00 -30.00   56
  7  ω     38.00  77.00   0.50    0.05    --   60.32-125.00   0.00   78
  8  ω     35.00  61.00   0.50    0.05    --   74.97-125.00 -30.00   52
  9  ω     37.00  98.00   0.50    0.05    --   74.97-125.00  30.00  122
 10  ω     49.00  96.00   0.50    0.05    --   74.97-125.00  90.00   94
 11  ω   -117.00 -83.00   0.50    0.05    --  -75.57 -15.00-180.00   68
 12  ω   -120.00 -59.00   0.50    0.05    --  -75.57 -15.00 -30.00  122
 13  ω   -119.00 -58.00   0.50    0.05    --  -75.57 -15.00  30.00  122
 14  ω   -118.00 -59.00   0.50    0.05    --  -75.57 -15.00  90.00  118
 15  ω    -59.00 -24.00   0.50    0.05    --  -60.72 125.00 -30.00   70
 16  ω    -85.00 -57.00   0.50    0.05    --  -60.72 125.00   0.00   56
 17  ω    -73.00 -47.00   0.50    0.05    --  -75.57 125.00 -30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0713207000
_diffrn_orient_matrix_UB_12      -0.0490051000
_diffrn_orient_matrix_UB_13      0.1086456000
_diffrn_orient_matrix_UB_21      -0.2622029000
_diffrn_orient_matrix_UB_22      -0.0466116000
_diffrn_orient_matrix_UB_23      -0.0431036000
_diffrn_orient_matrix_UB_31      0.0754591000
_diffrn_orient_matrix_UB_32      -0.2086685000
_diffrn_orient_matrix_UB_33      -0.0159100000
_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         0.443
_reflns_Friedel_fraction_full    0.546
_reflns_Friedel_fraction_max     0.516
_reflns_number_gt                1431
_reflns_number_total             1499
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.665
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.106
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.04(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1499
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0538
_refine_ls_restrained_S_all      1.067
_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)+(0.1152P)²+0.1389P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1539
_refine_ls_wR_factor_ref         0.1553
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C1(H1D,H1E,H1F)
;
_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
Br1 Br 0.96565(19) 0.91570(17) 0.92804(8) 0.0892(5) Uani 1 1 d . . . . .
Cl1 Cl 0.1884(3) 0.7421(3) 0.52634(16) 0.0679(6) Uani 1 1 d . . . . .
N1 N 0.3289(10) 0.3238(11) 0.5837(5) 0.0596(15) Uani 1 1 d . . . . .
H1A H 0.294814 0.445312 0.569654 0.089 Uiso 1 1 calc R U . . .
H1B H 0.208659 0.250570 0.556452 0.089 Uiso 1 1 calc R U . . .
H1C H 0.468823 0.292153 0.557490 0.089 Uiso 1 1 calc R U . . .
C1 C 0.456(3) 0.0974(18) 0.7195(10) 0.094(3) Uani 1 1 d . . . . .
H1D H 0.619861 0.089593 0.697962 0.141 Uiso 1 1 calc R U . . .
H1E H 0.355328 0.003886 0.683546 0.141 Uiso 1 1 calc R U . . .
H1F H 0.458377 0.074088 0.791820 0.141 Uiso 1 1 calc R U . . .
C2 C 0.3525(14) 0.2963(13) 0.6959(7) 0.0610(18) Uani 1 1 d . . . . .
H2 H 0.188129 0.302184 0.720830 0.073 Uiso 1 1 calc R U . . .
C3 C 0.5038(12) 0.4501(11) 0.7485(5) 0.0518(16) Uani 1 1 d . . . . .
C4 C 0.7036(12) 0.5345(12) 0.7071(5) 0.0534(16) Uani 1 1 d . . . . .
H4 H 0.744584 0.497654 0.642222 0.064 Uiso 1 1 calc R U . . .
C5 C 0.8417(14) 0.6701(13) 0.7588(6) 0.0583(17) Uani 1 1 d . . . . .
H5 H 0.975938 0.724082 0.730105 0.070 Uiso 1 1 calc R U . . .
C6 C 0.7778(14) 0.7257(13) 0.8551(6) 0.0598(18) Uani 1 1 d . . . . .
C7 C 0.5832(15) 0.6495(16) 0.8986(6) 0.066(2) Uani 1 1 d . . . . .
H7 H 0.544580 0.688453 0.963391 0.079 Uiso 1 1 calc R U . . .
C8 C 0.4405(15) 0.5117(14) 0.8451(6) 0.0621(19) Uani 1 1 d . . . . .
H8 H 0.303972 0.460923 0.873618 0.075 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 C6 1.900(8) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C2 1.478(11) . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C1 H1F 0.9600 . ?
C1 C2 1.531(15) . ?
C2 H2 0.9800 . ?
C2 C3 1.499(11) . ?
C3 C4 1.388(11) . ?
C3 C8 1.403(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.366(11) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(10) . ?
C6 C7 1.353(12) . ?
C7 H7 0.9300 . ?
C7 C8 1.400(13) . ?
C8 H8 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
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
N1 C2 C1 109.0(9) . . ?
N1 C2 H2 107.9 . . ?
N1 C2 C3 111.7(6) . . ?
C1 C2 H2 107.9 . . ?
C3 C2 C1 112.3(7) . . ?
C3 C2 H2 107.9 . . ?
C4 C3 C2 123.6(7) . . ?
C4 C3 C8 118.2(7) . . ?
C8 C3 C2 118.2(7) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.9(7) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.7(7) . . ?
C6 C5 H5 120.6 . . ?
C5 C6 Br1 119.4(6) . . ?
C7 C6 Br1 118.7(6) . . ?
C7 C6 C5 121.8(8) . . ?
C6 C7 H7 120.3 . . ?
C6 C7 C8 119.4(7) . . ?
C8 C7 H7 120.3 . . ?
C3 C8 H8 120.0 . . ?
C7 C8 C3 119.9(7) . . ?
C7 C8 H8 120.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A Cl1 0.89 2.23 3.116(8) 175.9 . yes
N1 H1B Cl1 0.89 2.36 3.138(6) 146.1 2_546 yes
N1 H1C Cl1 0.89 2.27 3.152(6) 172.0 2_646 yes

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 C6 C7 C8 178.9(7) . . . . ?
N1 C2 C3 C4 -35.2(10) . . . . ?
N1 C2 C3 C8 145.0(7) . . . . ?
C1 C2 C3 C4 87.5(10) . . . . ?
C1 C2 C3 C8 -92.2(10) . . . . ?
C2 C3 C4 C5 -177.9(7) . . . . ?
C2 C3 C8 C7 177.4(8) . . . . ?
C3 C4 C5 C6 -0.7(12) . . . . ?
C4 C3 C8 C7 -2.3(12) . . . . ?
C4 C5 C6 Br1 -179.5(6) . . . . ?
C4 C5 C6 C7 -0.1(13) . . . . ?
C5 C6 C7 C8 -0.4(14) . . . . ?
C6 C7 C8 C3 1.7(14) . . . . ?
C8 C3 C4 C5 1.9(11) . . . . ?


_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 11.407
_oxdiff_exptl_absorpt_empirical_full_min 0.415
####################################################################### 
# 
# 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_r_4_br_afla_ba_cl_300k_auto
_database_code_depnum_ccdc_archive 'CCDC 2516747'
loop_
_audit_author_name
_audit_author_address
'Xiaogang chen'
;Nanchang University
China
;
_audit_update_record             
;
2025-12-17 deposited with the CCDC.	2026-03-31 downloaded from the CCDC.
;
_audit_creation_date             2025-11-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H11 Br N, Cl'
_chemical_formula_sum            'C8 H11 Br Cl N'
_chemical_formula_weight         236.54
_chemical_absolute_configuration ?
_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'
Cl Cl 0.3639 0.7018 '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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.47653(10)
_cell_length_b                   7.02250(13)
_cell_length_c                   13.0992(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.0673(16)
_cell_angle_gamma                90
_cell_volume                     502.511(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4389
_cell_measurement_temperature    300.00(10)
_cell_measurement_theta_max      71.4800
_cell_measurement_theta_min      3.3680
_shelx_estimated_absorpt_T_max   0.584
_shelx_estimated_absorpt_T_min   0.398
_exptl_absorpt_coefficient_mu    7.538
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.129a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4930
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.594
_diffrn_reflns_theta_min         3.382
_diffrn_ambient_temperature      300.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     40.00 106.00   0.50    0.05    --   60.23  15.00-150.00  132
  2  ω     40.00 106.00   0.50    0.05    --   60.23  15.00 -90.00  132
  3  ω     40.00 106.00   0.50    0.05    --   60.23  15.00  90.00  132
  4  ω     55.00 121.00   0.50    0.05    --   74.99  15.00 150.00  132
  5  ω     55.00 121.00   0.50    0.05    --   74.99  15.00  90.00  132
  6  ω     55.00 121.00   0.50    0.05    --   74.99  15.00  30.00  132
  7  ω     40.00 106.00   0.50    0.05    --   60.23  15.00   0.00  132
  8  ω     40.00  81.00   0.50    0.05    --   60.23  15.00 -30.00   82
  9  ω     21.00  70.00   0.50    0.05    --   60.23-101.00 -80.00   98
 10  ω     18.00  84.00   0.50    0.05    --   60.23-125.00-120.00  132
 11  ω     33.00  99.00   0.50    0.05    --   75.12-125.00 -30.00  132
 12  ω     35.00  85.00   0.50    0.05    --   74.99-101.00 -80.00  100
 13  ω     18.00  84.00   0.50    0.05    --   60.23-125.00   0.00  132
 14  ω     33.00  99.00   0.50    0.05    --   75.12-125.00  60.00  132
 15  ω     18.00  84.00   0.50    0.05    --   60.23-125.00 150.00  132
 16  ω   -121.00 -57.00   0.50    0.05    --  -75.30 -15.00-120.00  128
 17  ω   -121.00 -57.00   0.50    0.05    --  -75.30 -15.00-180.00  128
 18  ω    -99.00 -32.00   0.50    0.05    --  -75.30 125.00-180.00  134
 19  ω    -99.00 -32.00   0.50    0.05    --  -75.30 125.00 -60.00  134
 20  ω    -85.00 -35.00   0.50    0.05    --  -75.30 101.00  23.00  100
 21  ω    -70.00 -21.00   0.50    0.05    --  -60.41 101.00  23.00   98
 22  ω    -98.00 -31.00   0.50    0.05    --  -74.13 125.00  90.00  134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    0.892
_reflns_Friedel_fraction_max     0.853
_reflns_number_gt                1733
_reflns_number_total             1802
_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 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.129a 64-bit (release 29-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details 
;
 Flack x determined using 698 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1802
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.198
_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)+(0.0997P)²+0.0623P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1484
_refine_ls_wR_factor_ref         0.1492
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C1(H1D,H1E,H1F)
;
_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
Br1 Br 0.03441(18) 0.09231(13) 0.07201(7) 0.0864(4) Uani 1 1 d . . . . .
Cl1 Cl 0.8118(3) 0.2662(3) 0.47376(14) 0.0652(5) Uani 1 1 d . . . . .
N1 N 0.6703(10) 0.6853(10) 0.4161(4) 0.0579(14) Uani 1 1 d . . . . .
H1A H 0.706781 0.564200 0.430036 0.069 Uiso 1 1 calc R U . . .
H1B H 0.529482 0.715079 0.442113 0.069 Uiso 1 1 calc R U . . .
H1C H 0.788751 0.760008 0.443523 0.069 Uiso 1 1 calc R U . . .
C1 C 0.539(2) 0.9101(14) 0.2797(9) 0.087(3) Uani 1 1 d . . . . .
H1D H 0.378142 0.917609 0.304373 0.131 Uiso 1 1 calc R U . . .
H1E H 0.528213 0.931031 0.207068 0.131 Uiso 1 1 calc R U . . .
H1F H 0.641989 1.005402 0.312822 0.131 Uiso 1 1 calc R U . . .
C2 C 0.6466(15) 0.7134(11) 0.3031(6) 0.0594(16) Uani 1 1 d . . . . .
H2 H 0.810873 0.709069 0.277950 0.071 Uiso 1 1 calc R U . . .
C3 C 0.4953(12) 0.5568(9) 0.2509(5) 0.0474(13) Uani 1 1 d . . . . .
C4 C 0.5594(16) 0.4971(12) 0.1555(6) 0.0607(17) Uani 1 1 d . . . . .
H4 H 0.695955 0.548781 0.127477 0.073 Uiso 1 1 calc R U . . .
C5 C 0.4185(16) 0.3589(14) 0.1013(5) 0.0658(19) Uani 1 1 d . . . . .
H5 H 0.458985 0.320089 0.036754 0.079 Uiso 1 1 calc R U . . .
C6 C 0.2190(14) 0.2809(11) 0.1447(5) 0.0565(16) Uani 1 1 d . . . . .
C7 C 0.1573(13) 0.3364(10) 0.2413(5) 0.0535(14) Uani 1 1 d . . . . .
H7 H 0.024648 0.281342 0.270720 0.064 Uiso 1 1 calc R U . . .
C8 C 0.2963(13) 0.4747(10) 0.2931(5) 0.0514(14) Uani 1 1 d . . . . .
H8 H 0.255137 0.513362 0.357553 0.062 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 C6 1.883(7) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C2 1.489(9) . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C1 H1F 0.9600 . ?
C1 C2 1.525(13) . ?
C2 H2 0.9800 . ?
C2 C3 1.511(10) . ?
C3 C4 1.386(10) . ?
C3 C8 1.383(10) . ?
C4 H4 0.9300 . ?
C4 C5 1.401(13) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(11) . ?
C6 C7 1.388(9) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(10) . ?
C8 H8 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
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
N1 C2 C1 109.0(8) . . ?
N1 C2 H2 108.2 . . ?
N1 C2 C3 111.1(6) . . ?
C1 C2 H2 108.2 . . ?
C3 C2 C1 112.1(7) . . ?
C3 C2 H2 108.2 . . ?
C4 C3 C2 117.5(6) . . ?
C8 C3 C2 123.0(6) . . ?
C8 C3 C4 119.4(6) . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0(7) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.3(6) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 Br1 118.9(5) . . ?
C5 C6 C7 121.0(7) . . ?
C7 C6 Br1 120.1(6) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 C6 118.9(6) . . ?
C8 C7 H7 120.6 . . ?
C3 C8 H8 119.3 . . ?
C7 C8 C3 121.3(6) . . ?
C7 C8 H8 119.4 . . ?

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 C6 C7 C8 179.8(5) . . . . ?
N1 C2 C3 C4 -145.2(7) . . . . ?
N1 C2 C3 C8 36.0(9) . . . . ?
C1 C2 C3 C4 92.7(9) . . . . ?
C1 C2 C3 C8 -86.2(9) . . . . ?
C2 C3 C4 C5 -176.9(7) . . . . ?
C2 C3 C8 C7 177.7(6) . . . . ?
C3 C4 C5 C6 -1.2(12) . . . . ?
C4 C3 C8 C7 -1.1(10) . . . . ?
C4 C5 C6 Br1 -179.0(6) . . . . ?
C4 C5 C6 C7 -0.5(12) . . . . ?
C5 C6 C7 C8 1.3(12) . . . . ?
C6 C7 C8 C3 -0.6(11) . . . . ?
C8 C3 C4 C5 2.0(11) . . . . ?


_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
;
####################################################################### 
# 
# 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_s_alfa_4_br_ba_cl_80k_auto
_database_code_depnum_ccdc_archive 'CCDC 2516743'
loop_
_audit_author_name
_audit_author_address
'Xiaogang chen'
;Nanchang University
China
;
_audit_update_record             
;
2025-12-17 deposited with the CCDC.	2026-03-31 downloaded from the CCDC.
;
_audit_creation_date             2025-11-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H11 Br N, Cl'
_chemical_formula_sum            'C8 H11 Br Cl N'
_chemical_formula_weight         236.54
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N Br Cl'
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'
Cl Cl 0.3639 0.7018 '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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.40890(10)
_cell_length_b                   6.8958(2)
_cell_length_c                   13.0697(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.133(2)
_cell_angle_gamma                90
_cell_volume                     486.75(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2327
_cell_measurement_temperature    80.00(18)
_cell_measurement_theta_max      71.7030
_cell_measurement_theta_min      3.3750
_shelx_estimated_absorpt_T_max   0.510
_shelx_estimated_absorpt_T_min   0.388
_exptl_absorpt_coefficient_mu    7.782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.129a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2578
_diffrn_reflns_point_group_measured_fraction_full 0.810
_diffrn_reflns_point_group_measured_fraction_max 0.777
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.928
_diffrn_reflns_theta_min         3.387
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      80.00(18)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     52.00  79.00   0.50    0.05    --   60.32  15.00-180.00   54
  2  ω     51.00 103.00   0.50    0.05    --   60.32  15.00-120.00  104
  3  ω     84.00 114.00   0.50    0.05    --   74.97  15.00-120.00   60
  4  ω     54.00 103.00   0.50    0.05    --   60.32  15.00 120.00   98
  5  ω     69.00 104.00   0.50    0.05    --   60.32  15.00 150.00   70
  6  ω     56.00 115.00   0.50    0.05    --   75.09  15.00 -60.00  118
  7  ω     58.00  83.00   0.50    0.05    --   74.97  15.00-120.00   50
  8  ω     55.00 112.00   0.50    0.05    --   74.97  15.00-180.00  114
  9  ω   -114.00 -68.00   0.50    0.05    --  -74.06 -15.00   0.00   92
 10  ω   -117.00 -58.00   0.50    0.05    --  -75.57 -15.00 -90.00  118
 11  ω    -73.00 -28.00   0.50    0.05    --  -60.72 125.00 -60.00   90
 12  ω    -96.00 -32.00   0.50    0.05    --  -74.06 125.00-120.00  128
 13  ω    -57.00 -27.00   0.50    0.05    --  -60.72 125.00-150.00   60
 14  ω    -82.00 -41.00   0.50    0.05    --  -75.57 125.00-180.00   82
 15  ω    -78.00 -53.00   0.50    0.05    --  -75.57 125.00-150.00   50
 16  ω    -97.00 -65.00   0.50    0.05    --  -75.57 125.00 150.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2252581000
_diffrn_orient_matrix_UB_12      -0.0133935000
_diffrn_orient_matrix_UB_13      0.0770388000
_diffrn_orient_matrix_UB_21      -0.1554415000
_diffrn_orient_matrix_UB_22      0.0861171000
_diffrn_orient_matrix_UB_23      0.0842160000
_diffrn_orient_matrix_UB_31      -0.0800009000
_diffrn_orient_matrix_UB_32      -0.2057466000
_diffrn_orient_matrix_UB_33      0.0302394000
_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         0.478
_reflns_Friedel_fraction_full    0.589
_reflns_Friedel_fraction_max     0.551
_reflns_number_gt                1481
_reflns_number_total             1491
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         2.618
_refine_diff_density_min         -1.285
_refine_diff_density_rms         0.207
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.03(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1491
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0554
_refine_ls_restrained_S_all      1.088
_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)+(0.1316P)²+0.8642P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1606
_refine_ls_wR_factor_ref         0.1608
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C1(H1D,H1E,H1F)
;
_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 0.97381(14) 0.91918(18) 0.92713(6) 0.0262(4) Uani 1 1 d . . . . .
Cl1 Cl 0.1873(4) 0.7373(3) 0.52843(16) 0.0225(5) Uani 1 1 d . . . . .
N1 N 0.3262(13) 0.3115(13) 0.5869(6) 0.0210(17) Uani 1 1 d . . . . .
H1A H 0.267915 0.433107 0.573271 0.031 Uiso 1 1 calc R U . . .
H1B H 0.217470 0.222649 0.559365 0.031 Uiso 1 1 calc R U . . .
H1C H 0.475610 0.296347 0.559133 0.031 Uiso 1 1 calc R U . . .
C1 C 0.4683(19) 0.0802(16) 0.7221(8) 0.027(2) Uani 1 1 d . . . . .
H1D H 0.632876 0.073740 0.694486 0.040 Uiso 1 1 calc R U . . .
H1E H 0.361250 -0.018984 0.689228 0.040 Uiso 1 1 calc R U . . .
H1F H 0.482491 0.057160 0.796225 0.040 Uiso 1 1 calc R U . . .
C2 C 0.3553(17) 0.2826(15) 0.7009(7) 0.0183(18) Uani 1 1 d . . . . .
H2 H 0.186606 0.284786 0.728591 0.022 Uiso 1 1 calc R U . . .
C3 C 0.5045(15) 0.4422(15) 0.7515(6) 0.0175(18) Uani 1 1 d . . . . .
C4 C 0.7104(16) 0.5238(14) 0.7082(6) 0.0181(18) Uani 1 1 d . . . . .
H4 H 0.756153 0.480772 0.642846 0.022 Uiso 1 1 calc R U . . .
C5 C 0.8494(16) 0.6666(16) 0.7592(7) 0.0208(19) Uani 1 1 d . . . . .
H5 H 0.985489 0.723934 0.727551 0.025 Uiso 1 1 calc R U . . .
C6 C 0.7901(16) 0.7256(16) 0.8558(7) 0.022(2) Uani 1 1 d . . . . .
C7 C 0.5822(17) 0.6467(17) 0.9014(7) 0.0219(19) Uani 1 1 d . . . . .
H7 H 0.537544 0.689741 0.966898 0.026 Uiso 1 1 calc R U . . .
C8 C 0.4427(17) 0.5039(15) 0.8484(7) 0.0195(18) Uani 1 1 d . . . . .
H8 H 0.303963 0.448266 0.878957 0.023 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 C6 1.881(11) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C2 1.502(11) . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C1 H1F 0.9800 . ?
C1 C2 1.543(14) . ?
C2 H2 1.0000 . ?
C2 C3 1.498(13) . ?
C3 C4 1.395(13) . ?
C3 C8 1.394(13) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(14) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(13) . ?
C6 C7 1.410(14) . ?
C7 H7 0.9500 . ?
C7 C8 1.401(15) . ?
C8 H8 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
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
N1 C2 C1 108.5(8) . . ?
N1 C2 H2 108.0 . . ?
C1 C2 H2 108.0 . . ?
C3 C2 N1 111.4(7) . . ?
C3 C2 C1 112.8(7) . . ?
C3 C2 H2 108.0 . . ?
C4 C3 C2 122.7(8) . . ?
C8 C3 C2 118.4(8) . . ?
C8 C3 C4 118.8(9) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.0(8) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.1(9) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 Br1 121.3(7) . . ?
C5 C6 C7 120.2(10) . . ?
C7 C6 Br1 118.4(7) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 C6 118.9(9) . . ?
C8 C7 H7 120.6 . . ?
C3 C8 C7 120.9(9) . . ?
C3 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A Cl1 0.91 2.21 3.116(9) 170.3 . yes
N1 H1B Cl1 0.91 2.42 3.129(7) 135.1 2_546 yes
N1 H1C Cl1 0.91 2.24 3.145(8) 171.6 2_646 yes

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 C6 C7 C8 179.3(7) . . . . ?
N1 C2 C3 C4 -38.9(12) . . . . ?
N1 C2 C3 C8 144.8(8) . . . . ?
C1 C2 C3 C4 83.4(11) . . . . ?
C1 C2 C3 C8 -92.9(10) . . . . ?
C2 C3 C4 C5 -177.6(9) . . . . ?
C2 C3 C8 C7 177.2(9) . . . . ?
C3 C4 C5 C6 2.3(14) . . . . ?
C4 C3 C8 C7 0.7(14) . . . . ?
C4 C5 C6 Br1 -179.9(7) . . . . ?
C4 C5 C6 C7 -2.6(14) . . . . ?
C5 C6 C7 C8 2.0(14) . . . . ?
C6 C7 C8 C3 -1.1(14) . . . . ?
C8 C3 C4 C5 -1.3(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 3.751
_oxdiff_exptl_absorpt_empirical_full_min 0.510
####################################################################### 
# 
# 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_r_4_br_afla_ba_cl_80k_auto
_database_code_depnum_ccdc_archive 'CCDC 2516745'
loop_
_audit_author_name
_audit_author_address
'Xiaogang chen'
;Nanchang University
China
;
_audit_update_record             
;
2025-12-17 deposited with the CCDC.	2026-03-31 downloaded from the CCDC.
;
_audit_creation_date             2024-11-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H11 Br N, Cl'
_chemical_formula_sum            'C8 H11 Br Cl N'
_chemical_formula_weight         236.54
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N Br Cl '
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'
Cl Cl 0.3639 0.7018 '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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.4123(2)
_cell_length_b                   6.8976(2)
_cell_length_c                   13.0668(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.236(3)
_cell_angle_gamma                90
_cell_volume                     487.03(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2607
_cell_measurement_temperature    80.0(4)
_cell_measurement_theta_max      71.0690
_cell_measurement_theta_min      3.3840
_shelx_estimated_absorpt_T_max   0.575
_shelx_estimated_absorpt_T_min   0.455
_exptl_absorpt_coefficient_mu    7.778
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.129a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2847
_diffrn_reflns_point_group_measured_fraction_full 0.831
_diffrn_reflns_point_group_measured_fraction_max 0.801
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.792
_diffrn_reflns_theta_min         3.388
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      80.0(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     29.00  55.00   0.50    0.05    --   60.23-102.00 -80.00   52
  2  ω     28.00  82.00   0.50    0.05    --   60.23-125.00   0.00  108
  3  ω     63.00  88.00   0.50    0.05    --   74.99-125.00   0.00   50
  4  ω     59.00  84.00   0.50    0.05    --   60.23-125.00  30.00   50
  5  ω     48.00  84.00   0.50    0.05    --   60.23-125.00 150.00   72
  6  ω     35.00  60.00   0.50    0.05    --   75.12-102.00 -80.00   50
  7  ω     44.00  87.00   0.50    0.05    --   60.23  15.00 -60.00   86
  8  ω     79.00 118.00   0.50    0.05    --   74.99  15.00-150.00   78
  9  ω     40.00  76.00   0.50    0.05    --   60.23  15.00-150.00   72
 10  ω   -107.00 -60.00   0.50    0.05    --  -75.50 -15.00-120.00   94
 11  ω   -120.00 -61.00   0.50    0.05    --  -75.50 -15.00 -60.00  118
 12  ω   -120.00 -61.00   0.50    0.05    --  -75.50 -15.00   0.00  118
 13  ω   -116.00 -80.00   0.50    0.05    --  -74.13 -15.00  60.00   72
 14  ω    -91.00 -48.00   0.50    0.05    --  -60.72 -15.00 150.00   86
 15  ω    -62.00 -24.00   0.50    0.05    --  -60.72 102.00  22.00   76
 16  ω    -83.00 -58.00   0.50    0.05    --  -74.13 102.00  22.00   50
 17  ω    -97.00 -46.00   0.50    0.05    --  -74.13 125.00 -30.00  102
 18  ω    -64.00 -39.00   0.50    0.05    --  -75.50 102.00  22.00   50
 19  ω    -99.00 -49.00   0.50    0.05    --  -75.50 125.00 -60.00  100
 20  ω    -98.00 -54.00   0.50    0.05    --  -75.50 125.00-120.00   88
 21  ω    -64.00 -35.00   0.50    0.05    --  -75.50 125.00-180.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0802756000
_diffrn_orient_matrix_UB_12      -0.1863344000
_diffrn_orient_matrix_UB_13      0.0539846000
_diffrn_orient_matrix_UB_21      0.0281197000
_diffrn_orient_matrix_UB_22      0.1040232000
_diffrn_orient_matrix_UB_23      0.1043678000
_diffrn_orient_matrix_UB_31      -0.2720210000
_diffrn_orient_matrix_UB_32      0.0658848000
_diffrn_orient_matrix_UB_33      -0.0120942000
_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         0.519
_reflns_Friedel_fraction_full    0.640
_reflns_Friedel_fraction_max     0.600
_reflns_number_gt                1516
_reflns_number_total             1530
_reflns_odcompleteness_completeness 99.17
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.129a 64-bit (release 29-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.883
_refine_diff_density_rms         0.152
_refine_ls_abs_structure_details 
;
 Flack x determined using 516 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1530
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0449
_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)+(0.0967P)²+1.0561P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1279
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C1(H1D,H1E,H1F)
;
_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
Br1 Br 0.97381(14) 0.08246(14) 0.92717(5) 0.0257(3) Uani 1 1 d . . . . .
Cl1 Cl 0.1877(3) 0.2647(3) 0.52845(13) 0.0212(4) Uani 1 1 d . . . . .
N1 N 0.3276(13) 0.6910(10) 0.5867(5) 0.0199(14) Uani 1 1 d . . . . .
H1A H 0.214504 0.776278 0.558827 0.024 Uiso 1 1 calc R U . . .
H1B H 0.275751 0.567672 0.573146 0.024 Uiso 1 1 calc R U . . .
H1C H 0.476146 0.710878 0.559089 0.024 Uiso 1 1 calc R U . . .
C1 C 0.4671(17) 0.9182(13) 0.7223(6) 0.0265(18) Uani 1 1 d . . . . .
H1D H 0.633476 0.922937 0.696358 0.040 Uiso 1 1 calc R U . . .
H1E H 0.477494 0.941324 0.796367 0.040 Uiso 1 1 calc R U . . .
H1F H 0.363447 1.018157 0.688200 0.040 Uiso 1 1 calc R U . . .
C2 C 0.3546(16) 0.7209(13) 0.7004(6) 0.0209(16) Uani 1 1 d . . . . .
H2 H 0.185805 0.718654 0.727821 0.025 Uiso 1 1 calc R U . . .
C3 C 0.5065(14) 0.5583(12) 0.7514(5) 0.0164(15) Uani 1 1 d . . . . .
C4 C 0.7115(14) 0.4760(10) 0.7084(5) 0.0149(15) Uani 1 1 d . . . . .
H4 H 0.755836 0.517456 0.642531 0.018 Uiso 1 1 calc R U . . .
C5 C 0.8517(14) 0.3352(12) 0.7597(6) 0.0189(15) Uani 1 1 d . . . . .
H5 H 0.990121 0.278473 0.729560 0.023 Uiso 1 1 calc R U . . .
C6 C 0.7853(15) 0.2789(11) 0.8564(6) 0.0181(15) Uani 1 1 d . . . . .
C7 C 0.5840(16) 0.3569(13) 0.9015(6) 0.0216(16) Uani 1 1 d . . . . .
H7 H 0.541867 0.315720 0.967644 0.026 Uiso 1 1 calc R U . . .
C8 C 0.4438(16) 0.4965(12) 0.8485(6) 0.0202(16) Uani 1 1 d . . . . .
H8 H 0.303644 0.550750 0.878530 0.024 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 C6 1.904(7) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C2 1.499(9) . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C1 H1F 0.9800 . ?
C1 C2 1.511(12) . ?
C2 H2 1.0000 . ?
C2 C3 1.522(12) . ?
C3 C4 1.393(11) . ?
C3 C8 1.398(10) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(11) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(11) . ?
C6 C7 1.377(12) . ?
C7 H7 0.9500 . ?
C7 C8 1.387(12) . ?
C8 H8 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
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
N1 C2 C1 109.1(6) . . ?
N1 C2 H2 108.2 . . ?
N1 C2 C3 110.7(6) . . ?
C1 C2 H2 108.2 . . ?
C1 C2 C3 112.3(6) . . ?
C3 C2 H2 108.2 . . ?
C4 C3 C2 123.1(6) . . ?
C4 C3 C8 118.8(7) . . ?
C8 C3 C2 118.0(7) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.2(7) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.3(7) . . ?
C6 C5 H5 120.8 . . ?
C5 C6 Br1 118.8(6) . . ?
C7 C6 Br1 119.0(6) . . ?
C7 C6 C5 122.1(7) . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C8 118.8(7) . . ?
C8 C7 H7 120.6 . . ?
C3 C8 H8 119.7 . . ?
C7 C8 C3 120.7(8) . . ?
C7 C8 H8 119.7 . . ?

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 C6 C7 C8 -178.5(6) . . . . ?
N1 C2 C3 C4 38.5(10) . . . . ?
N1 C2 C3 C8 -145.0(7) . . . . ?
C1 C2 C3 C4 -83.7(9) . . . . ?
C1 C2 C3 C8 92.9(9) . . . . ?
C2 C3 C4 C5 176.7(7) . . . . ?
C2 C3 C8 C7 -176.2(7) . . . . ?
C3 C4 C5 C6 -0.8(11) . . . . ?
C4 C3 C8 C7 0.5(12) . . . . ?
C4 C5 C6 Br1 179.1(6) . . . . ?
C4 C5 C6 C7 0.8(12) . . . . ?
C5 C6 C7 C8 -0.2(12) . . . . ?
C6 C7 C8 C3 -0.5(12) . . . . ?
C8 C3 C4 C5 0.2(11) . . . . ?


_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 3.396
_oxdiff_exptl_absorpt_empirical_full_min 0.537
####################################################################### 
# 
# 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_r_4_br_afla_ba_cl_390k_auto
_database_code_depnum_ccdc_archive 'CCDC 2516746'
loop_
_audit_author_name
_audit_author_address
'Xiaogang chen'
;Nanchang University
China
;
_audit_update_record             
;
2025-12-17 deposited with the CCDC.	2026-03-31 downloaded from the CCDC.
;
_audit_creation_date             2025-11-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H11 Br N, Cl'
_chemical_formula_sum            'C8 H11 Br Cl N'
_chemical_formula_weight         236.54
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N Br Cl '
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'
Cl Cl 0.3639 0.7018 '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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.5085(3)
_cell_length_b                   7.0767(4)
_cell_length_c                   13.1384(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.465(5)
_cell_angle_gamma                90
_cell_volume                     510.61(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2201
_cell_measurement_temperature    390.03(10)
_cell_measurement_theta_max      71.6170
_cell_measurement_theta_min      6.2270
_shelx_estimated_absorpt_T_max   0.524
_shelx_estimated_absorpt_T_min   0.402
_exptl_absorpt_coefficient_mu    7.418
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.129a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3000
_diffrn_reflns_point_group_measured_fraction_full 0.770
_diffrn_reflns_point_group_measured_fraction_max 0.740
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.236
_diffrn_reflns_theta_min         3.374
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      390.03(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     41.00  66.00   0.50    0.05    --   60.23-136.00 120.00   50
  2  ω     45.00  70.00   0.50    0.05    --   74.99-136.00 120.00   50
  3  ω     79.00 104.00   0.50    0.05    --   74.99-133.00 -61.00   50
  4  ω     61.00  98.00   0.50    0.05    --   75.12-125.00   0.00   74
  5  ω     61.00  86.00   0.50    0.05    --   60.23-133.00 -61.00   50
  6  ω     37.00  69.00   0.50    0.05    --   74.99-133.00 -61.00   64
  7  ω     65.00  99.00   0.50    0.05    --   75.12-125.00 -30.00   68
  8  ω     33.00  67.00   0.50    0.05    --   75.12-125.00 -90.00   68
  9  ω     34.00  80.00   0.50    0.05    --   60.23-125.00-120.00   92
 10  ω     41.00  81.00   0.50    0.05    --   60.23  15.00-180.00   80
 11  ω   -102.00 -59.00   0.50    0.05    --  -60.72 -15.00 -90.00   86
 12  ω   -106.00 -71.00   0.50    0.05    --  -60.72 -15.00-150.00   70
 13  ω   -113.00 -75.00   0.50    0.05    --  -75.50 -15.00-120.00   76
 14  ω   -117.00 -67.00   0.50    0.05    --  -74.13 -15.00 -90.00  100
 15  ω   -121.00 -59.00   0.50    0.05    --  -75.50 -15.00 -30.00  124
 16  ω    -55.00 -28.00   0.50    0.05    --  -60.72 136.00-174.00   54
 17  ω    -93.00 -68.00   0.50    0.05    --  -74.13 136.00-174.00   50
 18  ω    -68.00 -37.00   0.50    0.05    --  -75.50 125.00 -60.00   62
 19  ω    -54.00 -29.00   0.50    0.05    --  -60.72 133.00   7.00   50
 20  ω    -75.00 -31.00   0.50    0.05    --  -74.13 133.00   7.00   88
 21  ω   -104.00 -78.00   0.50    0.05    --  -74.13 133.00   7.00   52
 22  ω    -99.00 -45.00   0.50    0.05    --  -79.20 121.00 -21.51  108
 23  ω    -98.00 -72.00   0.50    0.05    --  -75.50 125.00 -60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0099254000
_diffrn_orient_matrix_UB_12      -0.1935117000
_diffrn_orient_matrix_UB_13      0.0537854000
_diffrn_orient_matrix_UB_21      0.0248600000
_diffrn_orient_matrix_UB_22      0.0994996000
_diffrn_orient_matrix_UB_23      0.1045726000
_diffrn_orient_matrix_UB_31      -0.2793662000
_diffrn_orient_matrix_UB_32      0.0020754000
_diffrn_orient_matrix_UB_33      0.0020226000
_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         0.433
_reflns_Friedel_fraction_full    0.526
_reflns_Friedel_fraction_max     0.489
_reflns_number_gt                1329
_reflns_number_total             1489
_reflns_odcompleteness_completeness 97.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.129a 64-bit (release 29-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 
;
 Flack x determined using 384 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1489
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.077
_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)+(0.1154P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.1585
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C1(H1D,H1E,H1F)
;
_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
Br1 Br 0.0382(2) 0.09832(15) 0.07178(9) 0.1205(6) Uani 1 1 d . . . . .
Cl1 Cl 0.8112(3) 0.2675(3) 0.47472(16) 0.0884(6) Uani 1 1 d . . . . .
N1 N 0.6709(10) 0.6849(11) 0.4170(5) 0.0783(16) Uani 1 1 d . . . . .
H1A H 0.713055 0.566053 0.431829 0.094 Uiso 1 1 calc R U . . .
H1B H 0.529336 0.710700 0.442243 0.094 Uiso 1 1 calc R U . . .
H1C H 0.784890 0.762804 0.444383 0.094 Uiso 1 1 calc R U . . .
C1 C 0.542(3) 0.9075(15) 0.2819(11) 0.126(4) Uani 1 1 d . . . . .
H1D H 0.406367 0.929532 0.322191 0.188 Uiso 1 1 calc R U . . .
H1E H 0.488037 0.915478 0.210775 0.188 Uiso 1 1 calc R U . . .
H1F H 0.665024 1.001074 0.298030 0.188 Uiso 1 1 calc R U . . .
C2 C 0.6471(15) 0.7099(12) 0.3056(7) 0.0810(19) Uani 1 1 d . . . . .
H2 H 0.810791 0.705337 0.281341 0.097 Uiso 1 1 calc R U . . .
C3 C 0.4981(12) 0.5577(10) 0.2518(5) 0.0666(15) Uani 1 1 d . . . . .
C4 C 0.2994(13) 0.4731(11) 0.2937(5) 0.0698(16) Uani 1 1 d . . . . .
H4 H 0.259574 0.509292 0.358427 0.084 Uiso 1 1 calc R U . . .
C5 C 0.1623(14) 0.3382(11) 0.2417(6) 0.0736(16) Uani 1 1 d . . . . .
H5 H 0.030234 0.283583 0.270459 0.088 Uiso 1 1 calc R U . . .
C6 C 0.2223(14) 0.2839(12) 0.1456(6) 0.0785(19) Uani 1 1 d . . . . .
C7 C 0.4181(16) 0.3614(17) 0.1019(6) 0.089(2) Uani 1 1 d . . . . .
H7 H 0.457687 0.323811 0.037429 0.107 Uiso 1 1 calc R U . . .
C8 C 0.5566(16) 0.4987(14) 0.1572(6) 0.082(2) Uani 1 1 d . . . . .
H8 H 0.691189 0.550905 0.129159 0.098 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 C6 1.882(7) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C2 1.470(11) . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C1 H1F 0.9600 . ?
C1 C2 1.537(14) . ?
C2 H2 0.9800 . ?
C2 C3 1.498(11) . ?
C3 C4 1.398(11) . ?
C3 C8 1.373(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.367(10) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(10) . ?
C6 C7 1.374(13) . ?
C7 H7 0.9300 . ?
C7 C8 1.403(14) . ?
C8 H8 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
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
N1 C2 C1 108.3(9) . . ?
N1 C2 H2 107.9 . . ?
N1 C2 C3 112.7(7) . . ?
C1 C2 H2 107.9 . . ?
C3 C2 C1 112.0(8) . . ?
C3 C2 H2 107.9 . . ?
C4 C3 C2 122.6(7) . . ?
C8 C3 C2 119.2(7) . . ?
C8 C3 C4 118.2(7) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.4(7) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.2(7) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 Br1 120.4(6) . . ?
C7 C6 Br1 118.2(6) . . ?
C7 C6 C5 121.4(7) . . ?
C6 C7 H7 120.9 . . ?
C6 C7 C8 118.2(7) . . ?
C8 C7 H7 120.9 . . ?
C3 C8 C7 121.6(8) . . ?
C3 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A Cl1 0.89 2.24 3.132(8) 177.8 . yes
N1 H1B Cl1 0.89 2.28 3.164(7) 173.2 2_656 yes

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 C6 C7 C8 -179.5(7) . . . . ?
N1 C2 C3 C4 34.5(10) . . . . ?
N1 C2 C3 C8 -145.9(7) . . . . ?
C1 C2 C3 C4 -88.0(11) . . . . ?
C1 C2 C3 C8 91.6(11) . . . . ?
C2 C3 C4 C5 178.1(7) . . . . ?
C2 C3 C8 C7 -177.7(8) . . . . ?
C3 C4 C5 C6 0.3(12) . . . . ?
C4 C3 C8 C7 1.9(12) . . . . ?
C4 C5 C6 Br1 179.9(6) . . . . ?
C4 C5 C6 C7 0.6(13) . . . . ?
C5 C6 C7 C8 -0.3(14) . . . . ?
C6 C7 C8 C3 -1.0(14) . . . . ?
C8 C3 C4 C5 -1.5(11) . . . . ?


_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 1.815
_oxdiff_exptl_absorpt_empirical_full_min 0.575
####################################################################### 
# 
# 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_rac_4_br_alfa_ba_cl_300k2_auto
_database_code_depnum_ccdc_archive 'CCDC 2516742'
loop_
_audit_author_name
_audit_author_address
'Xiaogang chen'
;Nanchang University
China
;
_audit_update_record             
;
2025-12-17 deposited with the CCDC.	2026-03-31 downloaded from the CCDC.
;
_audit_creation_date             2025-11-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H11 Br N, Cl'
_chemical_formula_sum            'C8 H11 Br Cl N'
_chemical_formula_weight         236.54
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N Cl Br '
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'
Cl Cl 0.3639 0.7018 '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           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   19.4511(12)
_cell_length_b                   14.2516(11)
_cell_length_c                   7.4067(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2053.2(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2828
_cell_measurement_temperature    300.00(10)
_cell_measurement_theta_max      71.5440
_cell_measurement_theta_min      3.8080
_shelx_estimated_absorpt_T_max   0.471
_shelx_estimated_absorpt_T_min   0.367
_exptl_absorpt_coefficient_mu    7.379
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87402
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.129a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10631
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.402
_diffrn_reflns_theta_min         3.845
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  60.00   0.50    0.50    --   60.54-138.00  56.00   50
  2  ω     46.00  71.00   0.50    0.50    --   75.12-138.00  56.00   50
  3  ω     52.00  92.00   0.50    0.50    --   75.18-125.00 -60.00   80
  4  ω     31.00  56.00   0.50    0.50    --   60.54-132.00-127.00   50
  5  ω     43.00  68.00   0.50    0.50    --   75.18-132.00-127.00   50
  6  ω     86.00 111.00   0.50    0.50    --   75.18  15.00-180.00   50
  7  ω     54.00  95.00   0.50    0.50    --   75.18-125.00   0.00   82
  8  ω     40.00  65.00   0.50    0.50    --   75.18-119.00 135.00   50
  9  ω     24.00  52.00   0.50    0.50    --   60.54-119.00 135.00   56
 10  ω   -103.00 -70.00   0.50    0.50    --  -60.72 -15.00-120.00   66
 11  ω    -96.00 -62.00   0.50    0.50    --  -75.50 -15.00-150.00   68
 12  ω   -104.00 -43.00   0.50    0.50    --  -60.72 -15.00-180.00  122
 13  ω    -80.00 -43.00   0.50    0.50    --  -60.72 -15.00 -60.00   74
 14  ω    -90.00 -58.00   0.50    0.50    --  -75.50 -15.00 -60.00   64
 15  ω   -120.00 -70.00   0.50    0.50    --  -75.50 -15.00  90.00  100
 16  ω    -97.00 -60.00   0.50    0.50    --  -79.20 116.00 164.41   74
 17  ω    -98.00 -47.00   0.50    0.50    --  -79.20 126.00 175.43  102
 18  ω    -94.00 -69.00   0.50    0.50    --  -75.50 138.00 118.00   50
 19  ω    -69.00 -44.00   0.50    0.50    --  -60.72 132.00 -57.00   50
 20  ω    -73.00 -48.00   0.50    0.50    --  -60.72 119.00-140.00   50
 21  ω    -88.00 -63.00   0.50    0.50    --  -75.50 119.00-140.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0785351000
_diffrn_orient_matrix_UB_12      -0.0044902000
_diffrn_orient_matrix_UB_13      0.0256181000
_diffrn_orient_matrix_UB_21      -0.0034301000
_diffrn_orient_matrix_UB_22      -0.1080040000
_diffrn_orient_matrix_UB_23      0.0033444000
_diffrn_orient_matrix_UB_31      0.0096611000
_diffrn_orient_matrix_UB_32      -0.0023745000
_diffrn_orient_matrix_UB_33      -0.2063287000
_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                988
_reflns_number_total             1994
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.00033(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   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1994
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1103
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.023
_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)+(0.0519P)²+1.7626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1537
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C1(H1D,H1E,H1F)
;
_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 0.32890(4) 0.32207(7) 0.79071(15) 0.1522(5) Uani 1 1 d . . . . .
Cl1 Cl 0.66687(6) 0.13775(9) 0.62397(17) 0.0723(4) Uani 1 1 d . . . . .
N1 N 0.67394(18) 0.3559(3) 0.7004(5) 0.0720(11) Uani 1 1 d . . . . .
H1A H 0.662807 0.298983 0.660664 0.086 Uiso 1 1 calc R U . . .
H1B H 0.668340 0.358341 0.819560 0.086 Uiso 1 1 calc R U . . .
H1C H 0.717641 0.367946 0.673276 0.086 Uiso 1 1 calc R U . . .
C1 C 0.6533(3) 0.5230(4) 0.6673(8) 0.1022(19) Uani 1 1 d . . . . .
H1D H 0.653479 0.527314 0.796641 0.153 Uiso 1 1 calc R U . . .
H1E H 0.623263 0.570119 0.618545 0.153 Uiso 1 1 calc R U . . .
H1F H 0.698999 0.532550 0.622266 0.153 Uiso 1 1 calc R U . . .
C2 C 0.6283(3) 0.4279(4) 0.6118(7) 0.0753(14) Uani 1 1 d . . . . .
H2 H 0.634383 0.422358 0.480913 0.090 Uiso 1 1 calc R U . . .
C3 C 0.5544(3) 0.4037(4) 0.6550(6) 0.0670(13) Uani 1 1 d . . . . .
C4 C 0.5122(3) 0.4631(4) 0.7511(7) 0.0786(15) Uani 1 1 d . . . . .
H4 H 0.528995 0.520617 0.790743 0.094 Uiso 1 1 calc R U . . .
C5 C 0.4454(3) 0.4379(5) 0.7889(7) 0.0867(17) Uani 1 1 d . . . . .
H5 H 0.417085 0.478692 0.852777 0.104 Uiso 1 1 calc R U . . .
C6 C 0.4210(3) 0.3545(5) 0.7339(8) 0.0904(17) Uani 1 1 d . . . . .
C7 C 0.4609(3) 0.2942(5) 0.6387(9) 0.106(2) Uani 1 1 d . . . . .
H7 H 0.443716 0.236374 0.601705 0.127 Uiso 1 1 calc R U . . .
C8 C 0.5270(3) 0.3197(4) 0.5978(8) 0.0904(17) Uani 1 1 d . . . . .
H8 H 0.554030 0.279214 0.529665 0.108 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 C6 1.896(6) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C2 1.506(6) . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C1 H1F 0.9600 . ?
C1 C2 1.497(7) . ?
C2 H2 0.9800 . ?
C2 C3 1.513(7) . ?
C3 C4 1.377(7) . ?
C3 C8 1.378(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.343(8) . ?
C6 C7 1.357(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.369(7) . ?
C8 H8 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
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
N1 C2 H2 107.8 . . ?
N1 C2 C3 108.2(4) . . ?
C1 C2 N1 107.8(4) . . ?
C1 C2 H2 107.8 . . ?
C1 C2 C3 117.1(5) . . ?
C3 C2 H2 107.8 . . ?
C4 C3 C2 122.4(5) . . ?
C4 C3 C8 117.5(5) . . ?
C8 C3 C2 120.1(5) . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.5(6) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(6) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 Br1 118.8(5) . . ?
C5 C6 C7 121.0(6) . . ?
C7 C6 Br1 120.1(5) . . ?
C6 C7 H7 120.5 . . ?
C6 C7 C8 119.0(6) . . ?
C8 C7 H7 120.5 . . ?
C3 C8 H8 119.1 . . ?
C7 C8 C3 121.8(5) . . ?
C7 C8 H8 119.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A Cl1 0.89 2.32 3.163(5) 159.3 . yes
N1 H1B Cl1 0.89 2.26 3.142(4) 173.6 7_566 yes
N1 H1C Cl1 0.89 2.28 3.149(4) 166.3 2_655 yes

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 C6 C7 C8 179.3(5) . . . . ?
N1 C2 C3 C4 118.0(5) . . . . ?
N1 C2 C3 C8 -62.0(6) . . . . ?
C1 C2 C3 C4 -4.1(7) . . . . ?
C1 C2 C3 C8 176.0(5) . . . . ?
C2 C3 C4 C5 -179.4(5) . . . . ?
C2 C3 C8 C7 178.1(5) . . . . ?
C3 C4 C5 C6 0.7(8) . . . . ?
C4 C3 C8 C7 -1.9(8) . . . . ?
C4 C5 C6 Br1 179.4(4) . . . . ?
C4 C5 C6 C7 -0.8(9) . . . . ?
C5 C6 C7 C8 -0.4(10) . . . . ?
C6 C7 C8 C3 1.8(10) . . . . ?
C8 C3 C4 C5 0.6(8) . . . . ?


_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 2.612
_oxdiff_exptl_absorpt_empirical_full_min 0.501
