# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 2208701'
loop_
_audit_author_name
_audit_author_address
'Zhirui Li'
;Xiamen university
China
;
_audit_update_record             
;
2022-09-22 deposited with the CCDC.	2024-10-07 downloaded from the CCDC.
;
_audit_creation_date             2022-03-31
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br4 Ga, C5 H13 Br N'
_chemical_formula_sum            'C5 H13 Br5 Ga N'
_chemical_formula_weight         556.43
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONGaBr5
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'
Ga Ga -1.2846 0.7763 '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           36
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   8.5264(3)
_cell_length_b                   12.9009(3)
_cell_length_c                   13.4160(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1475.74(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1832
_cell_measurement_temperature    300.00(10)
_cell_measurement_theta_max      74.2530
_cell_measurement_theta_min      6.2250
_shelx_estimated_absorpt_T_max   0.325
_shelx_estimated_absorpt_T_min   0.074
_exptl_absorpt_coefficient_mu    18.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
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    2.504
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.3
_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  0.0309
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2419
_diffrn_reflns_point_group_measured_fraction_full 0.765
_diffrn_reflns_point_group_measured_fraction_max 0.738
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.367
_diffrn_reflns_theta_min         6.222
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4741
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00 -13.00   1.00    1.00    --  -40.50 125.00-180.00   74
  2  ω   -114.00 -13.00   1.00    1.00    --  -40.50 -19.00 150.00  101
  3  ω     33.00 130.00   1.00    3.60    --  107.03 -77.00   0.00   97
  4  ω     27.00  94.00   1.00    3.60    --  107.03 -94.00 -60.00   67
  5  ω    114.00 173.00   1.00    3.60    --  107.03  77.00 -60.00   59
  6  ω    115.00 178.00   1.00    3.60    --  107.03  77.00-150.00   63
  7  ω     41.00 108.00   1.00    3.60    --  107.03-125.00-120.00   67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1198172000
_diffrn_orient_matrix_UB_12      -0.0875059000
_diffrn_orient_matrix_UB_13      -0.0178201000
_diffrn_orient_matrix_UB_21      -0.1268607000
_diffrn_orient_matrix_UB_22      0.0641952000
_diffrn_orient_matrix_UB_23      0.0535969000
_diffrn_orient_matrix_UB_31      -0.0466683000
_diffrn_orient_matrix_UB_32      0.0499524000
_diffrn_orient_matrix_UB_33      -0.0999489000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.441
_reflns_Friedel_fraction_full    0.512
_reflns_Friedel_fraction_max     0.473
_reflns_number_gt                1103
_reflns_number_total             1195
_reflns_odcompleteness_completeness 99.62
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.864
_refine_diff_density_min         -0.799
_refine_diff_density_rms         0.141
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.04(13)
_refine_ls_extinction_coef       0.00085(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     75
_refine_ls_number_reflns         1195
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0455
_refine_ls_restrained_S_all      1.095
_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)+(0.0798P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1167
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2-C3
 1.52 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C3 \\sim N1 \\sim C1 \\sim C4 \\sim C2 \\sim Br3: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02 within 2A
4. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H1C(0.5) C2(0.5) H2A(0.5) H2B(0.5) C3(0.5)
 H3A(0.5) H3B(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
5.b Me refined with riding coordinates:
 C1(H1A,H1B,H1C)
5.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_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
Ga1 Ga 0.0000 0.00441(12) 0.96428(14) 0.0452(4) Uani 1 2 d S T P . .
Br1 Br 0.0000 0.00052(16) 0.79096(14) 0.0665(5) Uani 1 2 d S T P . .
Br4 Br -0.22050(13) 0.09513(9) 1.01726(12) 0.0681(4) Uani 1 1 d . . . . .
Br2 Br 0.0000 -0.16161(11) 1.02799(19) 0.0762(6) Uani 1 2 d S T P . .
N1 N 0.0000 0.6419(12) 0.7127(12) 0.065(3) Uani 1 2 d S TU P . .
C1 C 0.0000 0.642(2) 0.6056(17) 0.093(6) Uani 1 2 d S TU P . .
H1A H -0.0912 0.6059 0.5818 0.140 Uiso 0.5 1 calc R U P A -1
H1B H -0.0014 0.7119 0.5817 0.140 Uiso 0.5 1 calc R U P A -1
H1C H 0.0926 0.6075 0.5818 0.140 Uiso 0.5 1 calc R U P A -1
C4 C 0.142(2) 0.6979(16) 0.7472(17) 0.102(5) Uani 1 1 d . U . . .
H4A H 0.2317 0.6531 0.7418 0.153 Uiso 1 1 calc R U . . .
H4B H 0.1286 0.7184 0.8154 0.153 Uiso 1 1 calc R U . . .
H4C H 0.1580 0.7583 0.7066 0.153 Uiso 1 1 calc R U . . .
Br3 Br 0.0000 0.33855(15) 0.8263(2) 0.0929(8) Uani 1 2 d S TU P . .
C2 C 0.067(4) 0.455(2) 0.750(2) 0.087(6) Uani 0.5 1 d D U P B -1
H2A H 0.1686 0.4778 0.7729 0.105 Uiso 0.5 1 calc R U P B -1
H2B H 0.0760 0.4350 0.6803 0.105 Uiso 0.5 1 calc R U P B -1
C3 C -0.051(3) 0.541(2) 0.760(2) 0.080(5) Uani 0.5 1 d D U P B -1
H3A H -0.1496 0.5197 0.7305 0.096 Uiso 0.5 1 calc R U P B -1
H3B H -0.0704 0.5535 0.8307 0.096 Uiso 0.5 1 calc R U P B -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ga1 Br1 2.326(2) . ?
Ga1 Br4 2.3258(14) 4 ?
Ga1 Br4 2.3258(14) . ?
Ga1 Br2 2.306(2) . ?
N1 C1 1.44(3) . ?
N1 C4 1.485(19) . ?
N1 C4 1.485(19) 4 ?
N1 C3 1.51(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
Br3 C2 1.90(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.511(12) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?

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
Br1 Ga1 Br4 108.44(7) . 4 ?
Br1 Ga1 Br4 108.44(7) . . ?
Br4 Ga1 Br4 107.87(10) 4 . ?
Br2 Ga1 Br1 110.52(11) . . ?
Br2 Ga1 Br4 110.74(7) . . ?
Br2 Ga1 Br4 110.74(7) . 4 ?
C1 N1 C4 108.2(13) . . ?
C1 N1 C4 108.2(13) . 4 ?
C1 N1 C3 115.0(19) . . ?
C4 N1 C4 109(2) . 4 ?
C4 N1 C3 92.8(13) 4 . ?
C4 N1 C3 121.5(17) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Br3 C2 H2A 109.8 . . ?
Br3 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 Br3 109(2) . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
N1 C3 C2 114(2) . . ?
N1 C3 H3A 108.8 . . ?
N1 C3 H3B 108.8 . . ?
C2 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?

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
C1 N1 C3 C2 71(2) . . . . ?
C4 N1 C3 C2 -62(3) . . . . ?
C4 N1 C3 C2 -177(2) 4 . . . ?
Br3 C2 C3 N1 173.0(19) . . . . ?

_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 3.341
_oxdiff_exptl_absorpt_empirical_full_min 0.635
