# Supplementary Information (SI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 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_cu_0709_02_0m
_database_code_depnum_ccdc_archive 'CCDC 2414415'
loop_
_audit_author_name
_audit_author_address
'Haijie Chen'
;Donghua University
China
;
_audit_update_record             
;
2025-01-04 deposited with the CCDC.	2025-03-17 downloaded from the CCDC.
;
_audit_creation_date             2024-07-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(Br), 0.5(C7 H8 N2 S)'
_chemical_formula_sum            'C3.50 H4 Br0.50 N S0.50'
_chemical_formula_weight         116.06
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.0857(6)
_cell_length_b                   13.9763(9)
_cell_length_c                   9.2460(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.277(4)
_cell_angle_gamma                90
_cell_volume                     874.33(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7584
_cell_measurement_temperature    304.00
_cell_measurement_theta_max      71.89
_cell_measurement_theta_min      5.93
_shelx_estimated_absorpt_T_max   0.461
_shelx_estimated_absorpt_T_min   0.085
_exptl_absorpt_coefficient_mu    8.121
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4061
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1572 before and 0.1079 after correction.
The Ratio of minimum to maximum transmission is 0.5389.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.5961
_exptl_crystal_size_mid          0.3297
_exptl_crystal_size_min          0.1127
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10497
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.669
_diffrn_reflns_theta_min         5.928
_diffrn_ambient_temperature      304.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1440
_reflns_number_total             1705
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.324
_refine_diff_density_min         -1.714
_refine_diff_density_rms         0.386
_refine_ls_extinction_coef       0.036(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1705
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0899
_refine_ls_restrained_S_all      1.156
_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)+(0.1498P)²+1.9865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2393
_refine_ls_wR_factor_ref         0.2519
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
2.b 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 0.51239(16) 0.36686(5) 0.08990(8) 0.0740(6) Uani 1 1 d . . . . .
S1 S 0.7164(2) 0.63623(10) 0.57850(17) 0.0472(6) Uani 1 1 d . . . . .
N1 N 0.5610(9) 0.6573(5) 0.2793(6) 0.0524(13) Uani 1 1 d . . . . .
H1A H 0.616407 0.650076 0.205250 0.063 Uiso 1 1 calc R U . . .
H1B H 0.575044 0.717695 0.311354 0.063 Uiso 1 1 calc R U . . .
H1C H 0.433077 0.643027 0.244744 0.063 Uiso 1 1 calc R U . . .
N2 N 0.6855(7) 0.5086(4) 0.3755(5) 0.0421(11) Uani 1 1 d . . . . .
H2 H 0.656739 0.480584 0.288837 0.051 Uiso 1 1 calc R U . . .
C1 C 0.6466(8) 0.6007(4) 0.3909(6) 0.0392(12) Uani 1 1 d . . . . .
C2 C 0.7761(8) 0.4613(4) 0.5102(6) 0.0418(13) Uani 1 1 d . . . . .
C3 C 0.8306(10) 0.3664(4) 0.5264(9) 0.0539(17) Uani 1 1 d . . . . .
H3 H 0.807506 0.326310 0.442584 0.065 Uiso 1 1 calc R U . . .
C4 C 0.9215(12) 0.3321(6) 0.6721(10) 0.069(2) Uani 1 1 d . . . . .
H4 H 0.959892 0.268292 0.686149 0.082 Uiso 1 1 calc R U . . .
C5 C 0.9556(13) 0.3930(7) 0.7976(10) 0.075(2) Uani 1 1 d . . . . .
H5 H 1.019253 0.369726 0.894039 0.090 Uiso 1 1 calc R U . . .
C6 C 0.8950(12) 0.4875(7) 0.7789(8) 0.067(2) Uani 1 1 d . . . . .
H6 H 0.913805 0.527477 0.862412 0.080 Uiso 1 1 calc R U . . .
C7 C 0.8062(8) 0.5218(5) 0.6343(6) 0.0457(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.729(5) . ?
S1 C7 1.742(7) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C1 1.299(8) . ?
N2 H2 0.8600 . ?
N2 C1 1.333(8) . ?
N2 C2 1.387(8) . ?
C2 C3 1.378(9) . ?
C2 C7 1.389(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.395(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.400(14) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(14) . ?
C6 H6 0.9300 . ?
C6 C7 1.383(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C7 90.2(3) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
C1 N2 H2 122.6 . . ?
C1 N2 C2 114.8(5) . . ?
C2 N2 H2 122.6 . . ?
N1 C1 S1 123.3(5) . . ?
N1 C1 N2 124.5(5) . . ?
N2 C1 S1 112.2(4) . . ?
N2 C2 C7 111.6(5) . . ?
C3 C2 N2 126.6(6) . . ?
C3 C2 C7 121.8(6) . . ?
C2 C3 H3 121.0 . . ?
C2 C3 C4 118.0(7) . . ?
C4 C3 H3 121.0 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(7) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.4(8) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.1(8) . . ?
C7 C6 H6 120.4 . . ?
C2 C7 S1 111.1(5) . . ?
C6 C7 S1 128.7(6) . . ?
C6 C7 C2 120.1(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
N2 C2 C3 C4 179.6(6) . . . . ?
N2 C2 C7 S1 0.9(6) . . . . ?
N2 C2 C7 C6 -180.0(6) . . . . ?
C1 S1 C7 C2 -1.3(4) . . . . ?
C1 S1 C7 C6 179.6(7) . . . . ?
C1 N2 C2 C3 179.5(6) . . . . ?
C1 N2 C2 C7 0.3(7) . . . . ?
C2 N2 C1 S1 -1.3(6) . . . . ?
C2 N2 C1 N1 -179.4(5) . . . . ?
C2 C3 C4 C5 0.0(11) . . . . ?
C3 C2 C7 S1 -178.4(5) . . . . ?
C3 C2 C7 C6 0.8(9) . . . . ?
C3 C4 C5 C6 1.6(13) . . . . ?
C4 C5 C6 C7 -2.0(13) . . . . ?
C5 C6 C7 S1 179.9(6) . . . . ?
C5 C6 C7 C2 0.9(11) . . . . ?
C7 S1 C1 N1 179.6(5) . . . . ?
C7 S1 C1 N2 1.5(4) . . . . ?
C7 C2 C3 C4 -1.2(9) . . . . ?

_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_mo_0217_05_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2414417'
loop_
_audit_author_name
_audit_author_address
'Haijie Chen'
;Donghua University
China
;
_audit_update_record             
;
2025-01-04 deposited with the CCDC.	2025-03-17 downloaded from the CCDC.
;
_audit_creation_date             2023-02-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Br), C8 H14 N2'
_chemical_formula_sum            'C8 H14 Br2 N2'
_chemical_formula_weight         298.03
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.6105(14)
_cell_length_b                   10.195(3)
_cell_length_c                   12.628(4)
_cell_angle_alpha                108.740(7)
_cell_angle_beta                 90.745(8)
_cell_angle_gamma                101.235(8)
_cell_volume                     549.5(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2079
_cell_measurement_temperature    297.00
_cell_measurement_theta_max      22.230
_cell_measurement_theta_min      3.387
_shelx_estimated_absorpt_T_max   0.765
_shelx_estimated_absorpt_T_min   0.245
_exptl_absorpt_coefficient_mu    7.330
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.2733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1649 before and 0.1026 after correction.
The Ratio of minimum to maximum transmission is 0.3666.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull light yellow'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.2673
_exptl_crystal_size_mid          0.1287
_exptl_crystal_size_min          0.0386
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1596
_diffrn_reflns_av_unetI/netI     0.0885
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17407
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.423
_diffrn_reflns_theta_min         2.158
_diffrn_ambient_temperature      297.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1546
_reflns_number_total             2245
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.745
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         2245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.031
_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)+0.0658P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.1072
_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 Secondary CH2 refined with riding coordinates:
 C1C(H1CA,H1CB), C2C(H2CA,H2CB)
2.b Aromatic/amide H refined with riding coordinates:
 C7C(H7C), C4C(H4C), C5C(H5C), C8C(H8C)
2.c Idealised Me refined as rotating group:
 N2N(H2NA,H2NB,H2NC), N1N(H1NA,H1NB,H1NC)
;
_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
Br1B Br 0.68650(13) 1.15943(6) 0.42669(4) 0.0427(2) Uani 1 1 d . . . . .
Br2B Br 1.30767(13) 0.90561(6) 0.10637(4) 0.0449(2) Uani 1 1 d . . . . .
N2N N 1.0585(10) 0.9025(5) 0.3477(3) 0.0392(11) Uani 1 1 d . . . . .
H2NA H 1.1729 0.9024 0.2914 0.047 Uiso 1 1 calc R U . . .
H2NB H 1.1650 0.8986 0.4054 0.047 Uiso 1 1 calc R U . . .
H2NC H 0.9877 0.9814 0.3685 0.047 Uiso 1 1 calc R U . . .
N1N N -0.0613(10) 0.1640(5) 0.1673(4) 0.0428(12) Uani 1 1 d . . . . .
H1NA H -0.1679 0.1567 0.1056 0.051 Uiso 1 1 calc R U . . .
H1NB H -0.1758 0.1743 0.2244 0.051 Uiso 1 1 calc R U . . .
H1NC H 0.0104 0.0860 0.1561 0.051 Uiso 1 1 calc R U . . .
C3C C 0.6647(11) 0.5146(6) 0.2424(4) 0.0362(12) Uani 1 1 d . . . . .
C1C C 0.8085(12) 0.7778(6) 0.3104(5) 0.0404(13) Uani 1 1 d . . . . .
H1CA H 0.6869 0.7845 0.2499 0.048 Uiso 1 1 calc R U . . .
H1CB H 0.6857 0.7771 0.3721 0.048 Uiso 1 1 calc R U . . .
C6C C 0.1865(12) 0.2881(5) 0.1935(4) 0.0362(13) Uani 1 1 d . . . . .
C7C C 0.2911(13) 0.3608(6) 0.3031(5) 0.0477(16) Uani 1 1 d . . . . .
H7C H 0.2026 0.3340 0.3609 0.057 Uiso 1 1 calc R U . . .
C4C C 0.5543(13) 0.4397(6) 0.1333(4) 0.0481(16) Uani 1 1 d . . . . .
H4C H 0.6424 0.4664 0.0755 0.058 Uiso 1 1 calc R U . . .
C2C C 0.9191(12) 0.6428(6) 0.2711(5) 0.0453(15) Uani 1 1 d . . . . .
H2CA H 1.0545 0.6400 0.3294 0.054 Uiso 1 1 calc R U . . .
H2CB H 1.0275 0.6399 0.2053 0.054 Uiso 1 1 calc R U . . .
C5C C 0.3177(13) 0.3267(6) 0.1076(5) 0.0478(16) Uani 1 1 d . . . . .
H5C H 0.2472 0.2770 0.0333 0.057 Uiso 1 1 calc R U . . .
C8C C 0.5276(14) 0.4734(7) 0.3266(5) 0.0530(17) Uani 1 1 d . . . . .
H8C H 0.5972 0.5233 0.4010 0.064 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
N2N H2NA 0.8900 . ?
N2N H2NB 0.8900 . ?
N2N H2NC 0.8900 . ?
N2N C1C 1.482(6) . ?
N1N H1NA 0.8900 . ?
N1N H1NB 0.8900 . ?
N1N H1NC 0.8900 . ?
N1N C6C 1.474(6) . ?
C3C C4C 1.377(7) . ?
C3C C2C 1.517(7) . ?
C3C C8C 1.381(7) . ?
C1C H1CA 0.9700 . ?
C1C H1CB 0.9700 . ?
C1C C2C 1.497(8) . ?
C6C C7C 1.372(7) . ?
C6C C5C 1.378(7) . ?
C7C H7C 0.9300 . ?
C7C C8C 1.371(7) . ?
C4C H4C 0.9300 . ?
C4C C5C 1.372(7) . ?
C2C H2CA 0.9700 . ?
C2C H2CB 0.9700 . ?
C5C H5C 0.9300 . ?
C8C H8C 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
H2NA N2N H2NB 109.5 . . ?
H2NA N2N H2NC 109.5 . . ?
H2NB N2N H2NC 109.5 . . ?
C1C N2N H2NA 109.5 . . ?
C1C N2N H2NB 109.5 . . ?
C1C N2N H2NC 109.5 . . ?
H1NA N1N H1NB 109.5 . . ?
H1NA N1N H1NC 109.5 . . ?
H1NB N1N H1NC 109.5 . . ?
C6C N1N H1NA 109.5 . . ?
C6C N1N H1NB 109.5 . . ?
C6C N1N H1NC 109.5 . . ?
C4C C3C C2C 121.7(5) . . ?
C4C C3C C8C 117.8(5) . . ?
C8C C3C C2C 120.4(5) . . ?
N2N C1C H1CA 109.4 . . ?
N2N C1C H1CB 109.4 . . ?
N2N C1C C2C 111.1(5) . . ?
H1CA C1C H1CB 108.0 . . ?
C2C C1C H1CA 109.4 . . ?
C2C C1C H1CB 109.4 . . ?
C7C C6C N1N 119.6(5) . . ?
C7C C6C C5C 120.7(5) . . ?
C5C C6C N1N 119.7(5) . . ?
C6C C7C H7C 120.4 . . ?
C8C C7C C6C 119.3(5) . . ?
C8C C7C H7C 120.4 . . ?
C3C C4C H4C 119.1 . . ?
C5C C4C C3C 121.8(5) . . ?
C5C C4C H4C 119.1 . . ?
C3C C2C H2CA 109.4 . . ?
C3C C2C H2CB 109.4 . . ?
C1C C2C C3C 111.2(5) . . ?
C1C C2C H2CA 109.4 . . ?
C1C C2C H2CB 109.4 . . ?
H2CA C2C H2CB 108.0 . . ?
C6C C5C H5C 120.5 . . ?
C4C C5C C6C 118.9(5) . . ?
C4C C5C H5C 120.5 . . ?
C3C C8C H8C 119.2 . . ?
C7C C8C C3C 121.5(5) . . ?
C7C C8C H8C 119.2 . . ?

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
N2N C1C C2C C3C 175.1(4) . . . . ?
N1N C6C C7C C8C 178.0(6) . . . . ?
N1N C6C C5C C4C -177.9(6) . . . . ?
C3C C4C C5C C6C 0.5(10) . . . . ?
C6C C7C C8C C3C -0.6(10) . . . . ?
C7C C6C C5C C4C -0.3(10) . . . . ?
C4C C3C C2C C1C 100.5(7) . . . . ?
C4C C3C C8C C7C 0.7(10) . . . . ?
C2C C3C C4C C5C -177.7(6) . . . . ?
C2C C3C C8C C7C 177.9(6) . . . . ?
C5C C6C C7C C8C 0.4(10) . . . . ?
C8C C3C C4C C5C -0.6(10) . . . . ?
C8C C3C C2C C1C -76.5(7) . . . . ?


_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_mo_0217_09_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2414416'
loop_
_audit_author_name
_audit_author_address
'Haijie Chen'
;Donghua University
China
;
_audit_update_record             
;
2025-01-04 deposited with the CCDC.	2025-03-17 downloaded from the CCDC.
;
_audit_creation_date             2023-02-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C9 H14 N'
_chemical_formula_sum            'C9 H14 Br N'
_chemical_formula_weight         216.12
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.1579(13)
_cell_length_b                   6.1222(4)
_cell_length_c                   9.0095(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.414(2)
_cell_angle_gamma                90
_cell_volume                     997.08(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3016
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      22.919
_cell_measurement_theta_min      3.381
_shelx_estimated_absorpt_T_max   0.917
_shelx_estimated_absorpt_T_min   0.173
_exptl_absorpt_coefficient_mu    4.065
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1374 before and 0.0709 after correction.
The Ratio of minimum to maximum transmission is 0.6996.
The λ/2 correction factor is Not present.
;
_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    1.440
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.6658
_exptl_crystal_size_mid          0.5939
_exptl_crystal_size_min          0.0217
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0908
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20766
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.411
_diffrn_reflns_theta_min         2.253
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1556
_reflns_number_total             2055
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0063(11)
_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   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         2055
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0278
_refine_ls_restrained_S_all      1.013
_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)+(0.0085P)²+0.3883P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0573
_refine_ls_wR_factor_ref         0.0639
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C2(H2)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C7(H7A,H7B,H7C)
;
_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 0.07126(2) 0.23295(4) 0.06860(3) 0.04916(13) Uani 1 1 d . . . . .
N1 N 0.07117(12) 0.7264(3) 0.2203(2) 0.0480(5) Uani 1 1 d . . . . .
H1A H 0.0785 0.6029 0.1716 0.058 Uiso 1 1 calc R U . . .
H1B H 0.0654 0.8363 0.1556 0.058 Uiso 1 1 calc R U . . .
H1C H 0.0307 0.7137 0.2683 0.058 Uiso 1 1 calc R U . . .
C4 C 0.26562(15) 0.9025(4) 0.3651(3) 0.0467(6) Uani 1 1 d . . . . .
C9 C 0.13564(15) 0.7698(4) 0.3286(3) 0.0485(6) Uani 1 1 d . . . . .
H9A H 0.1432 0.6459 0.3954 0.058 Uiso 1 1 calc R U . . .
H9B H 0.1254 0.8964 0.3880 0.058 Uiso 1 1 calc R U . . .
C8 C 0.20589(15) 0.8104(5) 0.2540(3) 0.0517(7) Uani 1 1 d . . . . .
H8A H 0.2228 0.6744 0.2136 0.062 Uiso 1 1 calc R U . . .
H8B H 0.1958 0.9123 0.1722 0.062 Uiso 1 1 calc R U . . .
C3 C 0.32806(17) 0.7850(5) 0.4133(3) 0.0590(7) Uani 1 1 d . . . . .
H3 H 0.3347 0.6461 0.3750 0.071 Uiso 1 1 calc R U . . .
C5 C 0.25797(17) 1.1088(5) 0.4240(3) 0.0567(7) Uani 1 1 d . . . . .
H5 H 0.2168 1.1929 0.3922 0.068 Uiso 1 1 calc R U . . .
C6 C 0.31092(18) 1.1916(5) 0.5296(4) 0.0632(8) Uani 1 1 d . . . . .
H6 H 0.3041 1.3297 0.5691 0.076 Uiso 1 1 calc R U . . .
C2 C 0.38112(18) 0.8705(6) 0.5179(4) 0.0689(9) Uani 1 1 d . . . . .
H2 H 0.4229 0.7881 0.5483 0.083 Uiso 1 1 calc R U . . .
C1 C 0.37329(17) 1.0747(5) 0.5776(3) 0.0627(8) Uani 1 1 d . . . . .
C7 C 0.4313(2) 1.1709(7) 0.6915(4) 0.0962(13) Uani 1 1 d . . . . .
H7A H 0.4314 1.3271 0.6821 0.144 Uiso 1 1 calc R U . . .
H7B H 0.4791 1.1147 0.6745 0.144 Uiso 1 1 calc R U . . .
H7C H 0.4200 1.1317 0.7900 0.144 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
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C9 1.476(3) . ?
C4 C8 1.513(4) . ?
C4 C3 1.378(4) . ?
C4 C5 1.382(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.517(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C3 H3 0.9300 . ?
C3 C2 1.385(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(4) . ?
C6 H6 0.9300 . ?
C6 C1 1.375(4) . ?
C2 H2 0.9300 . ?
C2 C1 1.373(4) . ?
C1 C7 1.519(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

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 . . ?
C9 N1 H1A 109.5 . . ?
C9 N1 H1B 109.5 . . ?
C9 N1 H1C 109.5 . . ?
C3 C4 C8 122.1(2) . . ?
C3 C4 C5 117.7(3) . . ?
C5 C4 C8 120.2(3) . . ?
N1 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
N1 C9 C8 112.6(2) . . ?
H9A C9 H9B 107.8 . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C4 C8 C9 110.4(2) . . ?
C4 C8 H8A 109.6 . . ?
C4 C8 H8B 109.6 . . ?
C9 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C4 C3 H3 119.5 . . ?
C4 C3 C2 121.1(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.2 . . ?
C1 C6 C5 121.6(3) . . ?
C1 C6 H6 119.2 . . ?
C3 C2 H2 119.4 . . ?
C1 C2 C3 121.3(3) . . ?
C1 C2 H2 119.4 . . ?
C6 C1 C7 120.6(3) . . ?
C2 C1 C6 117.6(3) . . ?
C2 C1 C7 121.8(3) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C9 C8 C4 167.4(2) . . . . ?
C4 C3 C2 C1 0.2(5) . . . . ?
C4 C5 C6 C1 1.3(5) . . . . ?
C8 C4 C3 C2 -178.4(3) . . . . ?
C8 C4 C5 C6 177.6(3) . . . . ?
C3 C4 C8 C9 111.5(3) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C3 C2 C1 C6 -0.1(5) . . . . ?
C3 C2 C1 C7 -179.6(3) . . . . ?
C5 C4 C8 C9 -67.2(3) . . . . ?
C5 C4 C3 C2 0.4(4) . . . . ?
C5 C6 C1 C2 -0.6(5) . . . . ?
C5 C6 C1 C7 178.8(3) . . . . ?


_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_mo_0217_12_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2414418'
loop_
_audit_author_name
_audit_author_address
'Haijie Chen'
;Donghua University
China
;
_audit_update_record             
;
2025-01-04 deposited with the CCDC.	2025-03-17 downloaded from the CCDC.
;
_audit_creation_date             2023-02-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Cl), C6 H16 N2'
_chemical_formula_sum            'C6 H16 Cl2 N2'
_chemical_formula_weight         187.11
_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'
Cl Cl 0.1484 0.1585 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.1895(8)
_cell_length_b                   15.941(2)
_cell_length_c                   17.606(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2017.7(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1246
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      22.444
_cell_measurement_theta_min      3.449
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.914
_exptl_absorpt_coefficient_mu    0.584
_exptl_absorpt_correction_T_max  0.7395
_exptl_absorpt_correction_T_min  0.6575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1536 before and 0.0847 after correction.
The Ratio of minimum to maximum transmission is 0.8891.
The λ/2 correction factor is Not present.
;
_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    1.232
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.1569
_exptl_crystal_size_mid          0.0987
_exptl_crystal_size_min          0.0557
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1760
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24058
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.498
_diffrn_reflns_theta_max         24.498
_diffrn_reflns_theta_min         2.314
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                906
_reflns_number_total             1686
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       0.0035(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   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1686
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.007
_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)+(0.0303P)²+0.5176P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.1076
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups, All N(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C6(H6A,H6B), C1(H1C,H1D), C3(H3A,H3B), C5(H5A,H5B), C4(H4A,H4B)
2.c Idealised Me refined as rotating group:
 N2(H2A,H2B,H2C)
;
_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
Cl2 Cl 0.00178(11) 0.40315(5) 0.60969(4) 0.0524(3) Uani 1 1 d . . . . .
Cl1 Cl 0.51115(11) 0.60116(5) 0.66256(4) 0.0534(3) Uani 1 1 d . . . . .
N1 N 0.4321(3) 0.41287(15) 0.62079(13) 0.0491(7) Uani 1 1 d . . . . .
H1A H 0.4637 0.4667 0.6246 0.059 Uiso 1 1 calc R U . . .
H1B H 0.3085 0.4099 0.6217 0.059 Uiso 1 1 calc R U . . .
N2 N 0.5518(3) 0.09052(14) 0.65653(14) 0.0532(7) Uani 1 1 d . . . . .
H2A H 0.5260 0.0372 0.6460 0.064 Uiso 1 1 calc R U . . .
H2B H 0.5033 0.1039 0.7014 0.064 Uiso 1 1 calc R U . . .
H2C H 0.6745 0.0976 0.6580 0.064 Uiso 1 1 calc R U . . .
C6 C 0.4518(4) 0.2877(2) 0.54066(16) 0.0460(8) Uani 1 1 d . . . . .
H6A H 0.5027 0.2659 0.4936 0.055 Uiso 1 1 calc R U . . .
H6B H 0.3177 0.2816 0.5386 0.055 Uiso 1 1 calc R U . . .
C2 C 0.5270(4) 0.23667(19) 0.60682(15) 0.0409(7) Uani 1 1 d . . . . .
H2 H 0.6631 0.2401 0.6060 0.049 Uiso 1 1 calc R U . . .
C1 C 0.4715(4) 0.14511(19) 0.59721(17) 0.0473(8) Uani 1 1 d . . . . .
H1C H 0.3370 0.1407 0.5988 0.057 Uiso 1 1 calc R U . . .
H1D H 0.5125 0.1256 0.5478 0.057 Uiso 1 1 calc R U . . .
C3 C 0.4585(4) 0.27473(19) 0.68119(17) 0.0495(9) Uani 1 1 d . . . . .
H3A H 0.3246 0.2683 0.6845 0.059 Uiso 1 1 calc R U . . .
H3B H 0.5138 0.2448 0.7235 0.059 Uiso 1 1 calc R U . . .
C5 C 0.5001(4) 0.37970(18) 0.54742(17) 0.0484(8) Uani 1 1 d . . . . .
H5A H 0.6339 0.3868 0.5442 0.058 Uiso 1 1 calc R U . . .
H5B H 0.4435 0.4106 0.5060 0.058 Uiso 1 1 calc R U . . .
C4 C 0.5078(4) 0.36660(19) 0.68670(18) 0.0515(8) Uani 1 1 d . . . . .
H4A H 0.4572 0.3898 0.7333 0.062 Uiso 1 1 calc R U . . .
H4B H 0.6419 0.3729 0.6882 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
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 C5 1.479(4) . ?
N1 C4 1.479(4) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N2 C1 1.477(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C2 1.520(4) . ?
C6 C5 1.512(4) . ?
C2 H2 0.9800 . ?
C2 C1 1.523(4) . ?
C2 C3 1.525(4) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.510(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 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
H1A N1 H1B 107.8 . . ?
C5 N1 H1A 109.1 . . ?
C5 N1 H1B 109.1 . . ?
C4 N1 H1A 109.1 . . ?
C4 N1 H1B 109.1 . . ?
C4 N1 C5 112.7(2) . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C1 N2 H2A 109.5 . . ?
C1 N2 H2B 109.5 . . ?
C1 N2 H2C 109.5 . . ?
H6A C6 H6B 107.9 . . ?
C2 C6 H6A 109.2 . . ?
C2 C6 H6B 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C5 C6 C2 112.2(2) . . ?
C6 C2 H2 108.3 . . ?
C6 C2 C1 109.5(2) . . ?
C6 C2 C3 109.3(2) . . ?
C1 C2 H2 108.3 . . ?
C1 C2 C3 113.1(2) . . ?
C3 C2 H2 108.3 . . ?
N2 C1 C2 112.6(2) . . ?
N2 C1 H1C 109.1 . . ?
N2 C1 H1D 109.1 . . ?
C2 C1 H1C 109.1 . . ?
C2 C1 H1D 109.1 . . ?
H1C C1 H1D 107.8 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 111.4(2) . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
N1 C5 C6 109.9(2) . . ?
N1 C5 H5A 109.7 . . ?
N1 C5 H5B 109.7 . . ?
C6 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
N1 C4 C3 110.3(2) . . ?
N1 C4 H4A 109.6 . . ?
N1 C4 H4B 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?

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
C6 C2 C1 N2 175.7(2) . . . . ?
C6 C2 C3 C4 -54.8(3) . . . . ?
C2 C6 C5 N1 -55.9(3) . . . . ?
C2 C3 C4 N1 56.4(3) . . . . ?
C1 C2 C3 C4 -177.1(3) . . . . ?
C3 C2 C1 N2 -62.2(3) . . . . ?
C5 N1 C4 C3 -58.0(3) . . . . ?
C5 C6 C2 C1 179.2(2) . . . . ?
C5 C6 C2 C3 54.8(3) . . . . ?
C4 N1 C5 C6 57.3(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
