# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_1-ADAB_298K
_database_code_depnum_ccdc_archive 'CCDC 2345092'
loop_
_audit_author_name
_audit_author_address
'Wei-Jian Xu'
;University of Aveiro
Portugal
;
_audit_update_record             
;
2024-04-01 deposited with the CCDC.	2025-05-08 downloaded from the CCDC.
;
_audit_creation_date             2024-01-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C10 H18 N'
_chemical_formula_sum            'C10 H18 Br N'
_chemical_formula_weight         232.16
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.3591(5)
_cell_length_b                   6.3615(2)
_cell_length_c                   14.7799(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.823(4)
_cell_angle_gamma                90
_cell_volume                     1037.08(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5416
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.6440
_cell_measurement_theta_min      2.0300
_shelx_estimated_absorpt_T_max   0.494
_shelx_estimated_absorpt_T_min   0.377
_exptl_absorpt_coefficient_mu    3.913
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17922
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.218
_diffrn_reflns_theta_min         2.584
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1967
_reflns_number_total             2990
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         2990
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0579
_refine_ls_restrained_S_all      1.075
_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)+(0.0226P)²+1.5085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0936
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C7(H7), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B), C4(H4A,H4B), C8(H8A,H8B), C6(H6A,H6B), C10(H10A,H10B)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_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 0.33254(3) 0.75279(6) 0.51811(2) 0.03776(11) Uani 1 1 d . . . . .
N1 N 0.4385(2) 0.2497(5) 0.58396(17) 0.0355(6) Uani 1 1 d . . . . .
H1A H 0.3968 0.3629 0.5594 0.043 Uiso 1 1 calc GR . . . .
H1B H 0.3918 0.1362 0.5702 0.043 Uiso 1 1 calc GR . . . .
H1C H 0.5034 0.2356 0.5607 0.043 Uiso 1 1 calc GR . . . .
C1 C 0.4781(3) 0.2742(5) 0.6884(2) 0.0248(6) Uani 1 1 d . . . . .
C9 C 0.6055(3) 0.4848(5) 0.8161(2) 0.0373(8) Uani 1 1 d . . . . .
H9 H 0.6623 0.6028 0.8312 0.045 Uiso 1 1 calc R . . . .
C7 C 0.4054(4) 0.3452(6) 0.8309(3) 0.0403(9) Uani 1 1 d . . . . .
H7 H 0.3342 0.3745 0.8553 0.048 Uiso 1 1 calc R . . . .
C3 C 0.5673(3) 0.4559(5) 0.7104(2) 0.0285(7) Uani 1 1 d . . . . .
H3A H 0.5297 0.5836 0.6812 0.034 Uiso 1 1 calc R . . . .
H3B H 0.6379 0.4262 0.6863 0.034 Uiso 1 1 calc R . . . .
C2 C 0.3665(3) 0.3175(5) 0.7251(2) 0.0333(8) Uani 1 1 d . . . . .
H2A H 0.3100 0.2012 0.7097 0.040 Uiso 1 1 calc R . . . .
H2B H 0.3264 0.4439 0.6965 0.040 Uiso 1 1 calc R . . . .
C4 C 0.5383(3) 0.0716(5) 0.7312(2) 0.0323(8) Uani 1 1 d . . . . .
H4A H 0.6083 0.0409 0.7067 0.039 Uiso 1 1 calc R . . . .
H4B H 0.4818 -0.0447 0.7159 0.039 Uiso 1 1 calc R . . . .
C8 C 0.4943(4) 0.5287(5) 0.8533(2) 0.0430(9) Uani 1 1 d . . . . .
H8A H 0.4552 0.6565 0.8254 0.052 Uiso 1 1 calc R . . . .
H8B H 0.5186 0.5491 0.9203 0.052 Uiso 1 1 calc R . . . .
C5 C 0.5775(3) 0.0992(5) 0.8372(2) 0.0392(9) Uani 1 1 d . . . . .
H5 H 0.6170 -0.0299 0.8655 0.047 Uiso 1 1 calc R . . . .
C6 C 0.4670(4) 0.1434(6) 0.8751(3) 0.0467(10) Uani 1 1 d . . . . .
H6A H 0.4912 0.1592 0.9422 0.056 Uiso 1 1 calc R . . . .
H6B H 0.4107 0.0267 0.8608 0.056 Uiso 1 1 calc R . . . .
C10 C 0.6668(4) 0.2831(5) 0.8607(3) 0.0474(10) Uani 1 1 d . . . . .
H10A H 0.6924 0.3005 0.9277 0.057 Uiso 1 1 calc R . . . .
H10B H 0.7381 0.2542 0.8373 0.057 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.509(4) . ?
C1 C3 1.520(4) . ?
C1 C2 1.518(4) . ?
C1 C4 1.524(4) . ?
C9 C3 1.529(5) . ?
C9 C8 1.519(5) . ?
C9 C10 1.532(5) . ?
C7 C2 1.530(5) . ?
C7 C8 1.528(5) . ?
C7 C6 1.531(5) . ?
C4 C5 1.533(5) . ?
C5 C6 1.518(5) . ?
C5 C10 1.533(5) . ?

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
N1 C1 C3 108.5(3) . . ?
N1 C1 C2 108.3(3) . . ?
N1 C1 C4 109.4(3) . . ?
C3 C1 C4 110.1(2) . . ?
C2 C1 C3 110.9(3) . . ?
C2 C1 C4 109.6(3) . . ?
C3 C9 C10 109.1(3) . . ?
C8 C9 C3 109.6(3) . . ?
C8 C9 C10 109.3(3) . . ?
C2 C7 C6 109.3(3) . . ?
C8 C7 C2 109.0(3) . . ?
C8 C7 C6 109.7(3) . . ?
C1 C3 C9 108.8(3) . . ?
C1 C2 C7 108.9(3) . . ?
C1 C4 C5 108.6(3) . . ?
C9 C8 C7 110.1(3) . . ?
C4 C5 C10 109.5(3) . . ?
C6 C5 C4 109.5(3) . . ?
C6 C5 C10 109.6(3) . . ?
C5 C6 C7 109.4(3) . . ?
C9 C10 C5 109.5(3) . . ?

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
N1 H1A Br1 0.89 2.62 3.475(3) 162.5 .
N1 H1B Br1 0.89 2.60 3.439(3) 158.1 1_545
N1 H1C Br1 0.89 2.42 3.304(3) 170.6 3_666

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

data_2-ADAB_298K
_database_code_depnum_ccdc_archive 'CCDC 2345093'
loop_
_audit_author_name
_audit_author_address
'Wei-Jian Xu'
;University of Aveiro
Portugal
;
_audit_update_record             
;
2024-04-01 deposited with the CCDC.	2025-05-08 downloaded from the CCDC.
;
_audit_creation_date             2024-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C10 H18 N'
_chemical_formula_sum            'C10 H18 Br N'
_chemical_formula_weight         232.16
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.7656(3)
_cell_length_b                   6.4026(2)
_cell_length_c                   10.1581(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.526(4)
_cell_angle_gamma                90
_cell_volume                     493.04(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4019
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      29.7180
_cell_measurement_theta_min      2.0520
_shelx_estimated_absorpt_T_max   0.479
_shelx_estimated_absorpt_T_min   0.353
_exptl_absorpt_coefficient_mu    4.116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69292
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7256
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.952
_diffrn_reflns_theta_min         2.054
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                2328
_reflns_number_total             2685
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.18(2)
_refine_ls_extinction_coef       0.065(5)
_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   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2685
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.054
_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)+(0.0344P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0689
_refine_ls_wR_factor_ref         0.0712
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.82(2)
 0.18(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All N(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C7(H7), C2(H2), C1(H1), C9(H9), C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C8(H8A,H8B), C3(H3A,H3B), C5(H5A,H5B), C4(H4A,H4B)
3.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_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 0.66952(4) 0.32137(15) 0.16293(3) 0.03134(13) Uani 1 1 d . . . . .
N1 N 0.4968(3) 0.8243(10) 0.1658(2) 0.0275(5) Uani 1 1 d . . . . .
H1A H 0.4142 0.8221 0.0899 0.041 Uiso 1 1 calc GR . . . .
H1B H 0.5589 0.7064 0.1730 0.041 Uiso 1 1 calc GR . . . .
H1C H 0.5683 0.9326 0.1644 0.041 Uiso 1 1 calc GR . . . .
C7 C 0.2854(6) 1.0284(8) 0.2700(5) 0.0248(10) Uani 1 1 d . . . . .
H7 H 0.3462 1.1564 0.2528 0.030 Uiso 1 1 calc R . . . .
C10 C -0.0324(4) 0.8136(13) 0.3147(3) 0.0286(7) Uani 1 1 d . . . . .
H10A H -0.0945 0.6888 0.3323 0.034 Uiso 1 1 calc R . . . .
H10B H -0.1126 0.9311 0.3086 0.034 Uiso 1 1 calc R . . . .
C2 C 0.3141(6) 0.6419(8) 0.3058(5) 0.0249(11) Uani 1 1 d . . . . .
H2 H 0.3955 0.5236 0.3118 0.030 Uiso 1 1 calc R . . . .
C8 C 0.1225(7) 0.9888(8) 0.1536(4) 0.0272(11) Uani 1 1 d . . . . .
H8A H 0.0423 1.1064 0.1458 0.033 Uiso 1 1 calc R . . . .
H8B H 0.1602 0.9745 0.0690 0.033 Uiso 1 1 calc R . . . .
C3 C 0.1557(5) 0.6051(8) 0.1919(4) 0.0269(11) Uani 1 1 d . . . . .
H3A H 0.0966 0.4773 0.2081 0.032 Uiso 1 1 calc R . . . .
H3B H 0.1939 0.5899 0.1076 0.032 Uiso 1 1 calc R . . . .
C5 C 0.2219(6) 1.0485(7) 0.4019(4) 0.0291(10) Uani 1 1 d . . . . .
H5A H 0.3220 1.0746 0.4757 0.035 Uiso 1 1 calc R . . . .
H5B H 0.1417 1.1660 0.3959 0.035 Uiso 1 1 calc R . . . .
C1 C 0.4105(4) 0.8444(9) 0.2847(3) 0.0207(9) Uani 1 1 d . . . . .
H1 H 0.5037 0.8676 0.3654 0.025 Uiso 1 1 calc R . . . .
C9 C 0.0280(4) 0.7892(8) 0.1820(3) 0.0273(11) Uani 1 1 d . . . . .
H9 H -0.0747 0.7646 0.1085 0.033 Uiso 1 1 calc R . . . .
C6 C 0.1284(4) 0.8495(9) 0.4299(3) 0.0268(11) Uani 1 1 d . . . . .
H6 H 0.0897 0.8642 0.5151 0.032 Uiso 1 1 calc R . . . .
C4 C 0.2537(6) 0.6642(7) 0.4391(4) 0.0281(10) Uani 1 1 d . . . . .
H4A H 0.1943 0.5376 0.4572 0.034 Uiso 1 1 calc R . . . .
H4B H 0.3552 0.6856 0.5124 0.034 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.509(4) . ?
C7 C8 1.554(6) . ?
C7 C5 1.530(6) . ?
C7 C1 1.514(7) . ?
C10 C9 1.528(5) . ?
C10 C6 1.532(5) . ?
C2 C3 1.513(6) . ?
C2 C1 1.535(7) . ?
C2 C4 1.533(6) . ?
C8 C9 1.532(7) . ?
C3 C9 1.530(7) . ?
C5 C6 1.524(7) . ?
C6 C4 1.525(7) . ?

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
C5 C7 C8 108.5(3) . . ?
C1 C7 C8 110.3(4) . . ?
C1 C7 C5 107.5(4) . . ?
C9 C10 C6 109.5(3) . . ?
C3 C2 C1 111.4(4) . . ?
C3 C2 C4 109.7(4) . . ?
C4 C2 C1 107.2(3) . . ?
C9 C8 C7 109.7(4) . . ?
C2 C3 C9 109.8(4) . . ?
C6 C5 C7 110.5(4) . . ?
N1 C1 C7 112.0(4) . . ?
N1 C1 C2 110.8(4) . . ?
C7 C1 C2 110.4(3) . . ?
C10 C9 C8 109.4(5) . . ?
C10 C9 C3 109.8(4) . . ?
C3 C9 C8 108.9(3) . . ?
C5 C6 C10 109.0(4) . . ?
C5 C6 C4 109.8(3) . . ?
C4 C6 C10 109.5(5) . . ?
C6 C4 C2 109.4(3) . . ?

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
N1 H1B Br1 0.89 2.62 3.491(6) 166.2 .
N1 H1C Br1 0.89 2.61 3.456(6) 158.7 1_565

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.82(2)
2 0.18(2)

####################################################################### 
# 
# 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-ADAB_393K
_database_code_depnum_ccdc_archive 'CCDC 2345094'
loop_
_audit_author_name
_audit_author_address
'Wei-Jian Xu'
;University of Aveiro
Portugal
;
_audit_update_record             
;
2024-04-01 deposited with the CCDC.	2025-05-08 downloaded from the CCDC.
;
_audit_creation_date             2024-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C10 H18 N'
_chemical_formula_sum            'C10 H18 Br N'
_chemical_formula_weight         232.16
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   7.8338(4)
_cell_length_b                   6.4470(4)
_cell_length_c                   10.1896(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.173(6)
_cell_angle_gamma                90
_cell_volume                     503.05(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3489
_cell_measurement_temperature    393
_cell_measurement_theta_max      27.1180
_cell_measurement_theta_min      2.0360
_shelx_estimated_absorpt_T_max   0.485
_shelx_estimated_absorpt_T_min   0.358
_exptl_absorpt_coefficient_mu    4.034
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7881
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.900
_diffrn_reflns_theta_min         2.045
_diffrn_ambient_temperature      393
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1216
_reflns_number_total             1674
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.942
_refine_diff_density_rms         0.133
_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     65
_refine_ls_number_reflns         1674
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.068
_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)+(0.0546P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1049
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
2. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H1C(0.5) H5A(0.5) H5B(0.5)
3.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C3(H3A,H3B)
3.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_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 0.66851(5) 0.2500 0.16251(3) 0.04611(17) Uani 1 2 d S T P . .
N1 N 0.4974(4) 0.7500 0.1666(3) 0.0421(7) Uani 1 2 d S T P . .
H1A H 0.5849 0.6591 0.1807 0.050 Uiso 0.5 1 calc GR . . A -1
H1B H 0.5388 0.8761 0.1561 0.050 Uiso 0.5 1 calc GR . . A -1
H1C H 0.4199 0.7148 0.0929 0.050 Uiso 0.5 1 calc GR . . A -1
C1 C 0.4108(4) 0.7500 0.2849(3) 0.0363(8) Uani 1 2 d S T P . .
H1 H 0.5030 0.7500 0.3665 0.044 Uiso 1 2 calc RS T P . .
C5 C -0.0289(4) 0.7500 0.3131(3) 0.0474(9) Uani 1 2 d S T P . .
H5A H -0.0998 0.6281 0.3182 0.057 Uiso 0.5 1 calc R . . . .
H5B H -0.0998 0.8719 0.3182 0.057 Uiso 0.5 1 calc R . . . .
C2 C 0.3007(3) 0.5574(4) 0.2878(3) 0.0456(6) Uani 1 1 d . . . . .
H2 H 0.3708 0.4331 0.2824 0.055 Uiso 1 1 calc R . . . .
C4 C 0.1283(5) 0.7500 0.4294(4) 0.0453(9) Uani 1 2 d S T P . .
H4 H 0.0893 0.7500 0.5147 0.054 Uiso 1 2 calc RS T P . .
C6 C 0.0316(5) 0.7500 0.1816(4) 0.0522(11) Uani 1 2 d S T P . .
H6 H -0.0702 0.7500 0.1068 0.063 Uiso 1 2 calc RS T P . .
C7 C 0.1417(4) 0.9407(6) 0.1725(3) 0.0597(9) Uani 1 1 d . . . . .
H7A H 0.0726 1.0646 0.1761 0.072 Uiso 1 1 calc R . . . .
H7B H 0.1792 0.9403 0.0876 0.072 Uiso 1 1 calc R . . . .
C3 C 0.2385(4) 0.5586(5) 0.4207(3) 0.0632(9) Uani 1 1 d . . . . .
H3A H 0.1700 0.4350 0.4269 0.076 Uiso 1 1 calc R . . . .
H3B H 0.3387 0.5577 0.4952 0.076 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.503(4) . ?
C1 C2 1.516(3) 4_575 ?
C1 C2 1.516(3) . ?
C5 C4 1.519(5) . ?
C5 C6 1.512(5) . ?
C2 C7 1.522(4) 4_575 ?
C2 C3 1.533(4) . ?
C4 C3 1.519(4) . ?
C4 C3 1.519(4) 4_575 ?
C6 C7 1.516(4) . ?
C6 C7 1.516(4) 4_575 ?
C7 C2 1.522(4) 4_575 ?

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
N1 C1 C2 111.78(19) . 4_575 ?
N1 C1 C2 111.78(19) . . ?
C2 C1 C2 110.0(3) 4_575 . ?
C6 C5 C4 109.7(3) . . ?
C1 C2 C7 110.8(2) . 4_575 ?
C1 C2 C3 107.5(3) . . ?
C7 C2 C3 108.8(2) 4_575 . ?
C3 C4 C5 109.4(2) . . ?
C3 C4 C5 109.4(2) 4_575 . ?
C3 C4 C3 108.7(3) . 4_575 ?
C5 C6 C7 110.1(2) . . ?
C5 C6 C7 110.1(2) . 4_575 ?
C7 C6 C7 108.4(3) . 4_575 ?
C6 C7 C2 110.0(2) . 4_575 ?
C4 C3 C2 110.2(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
N1 H1A Br1 0.89 2.73 3.4946(12) 144.3 .
N1 H1B Br1 0.89 2.61 3.4946(12) 171.9 1_565
N1 H1C Br1 0.89 2.56 3.331(3) 145.7 2_655

_olex2_submission_special_instructions 'No special instructions were received'
