# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_From_MeCN
_database_code_depnum_ccdc_archive 'CCDC 2124411'
loop_
_audit_author_name
_audit_author_address
'Shohei Tashiro'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H8 Br2 N, Br'
_chemical_formula_sum            'C7 H8 Br3 N'
_chemical_formula_weight         345.87
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHN
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.12360(10)
_cell_length_b                   14.0468(2)
_cell_length_c                   16.9496(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1934.13(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4183
_cell_measurement_temperature    93
_cell_measurement_theta_max      71.9070
_cell_measurement_theta_min      6.7860
_shelx_estimated_absorpt_T_max   0.467
_shelx_estimated_absorpt_T_min   0.137
_exptl_absorpt_coefficient_mu    14.976
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    2.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5588
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.041
_diffrn_reflns_theta_min         5.219
_diffrn_ambient_temperature      93
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00   2.00   0.50    0.50    --    0.00  82.00-120.00   54
  2  ω    -60.00 -21.00   0.50    0.50    --    0.00 -38.00 -90.00   78
  3  ω    -12.00  27.00   0.50    0.50    --    0.00 -38.00 -90.00   78
  4  ω     41.00  88.00   0.50    0.50    --    0.00  82.00-120.00   94
  5  ω     16.00 106.00   0.50    0.50    --   95.70 -82.00  60.00  180
  6  ω     27.00 113.00   0.50    0.50    --   95.70 -45.00-150.00  172
  7  ω     83.00 126.00   0.50    0.50    --   95.70 -82.00 -30.00   86
  8  ω     90.00 126.00   0.50    0.50    --   95.70 -77.00  30.00   72
  9  ω     19.00 122.00   0.50    0.50    --   95.70 -15.00  90.00  206
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1305261000
_diffrn_orient_matrix_UB_12      -0.0041612000
_diffrn_orient_matrix_UB_13      0.0657524000
_diffrn_orient_matrix_UB_21      0.1377412000
_diffrn_orient_matrix_UB_22      0.0061127000
_diffrn_orient_matrix_UB_23      -0.0624234000
_diffrn_orient_matrix_UB_31      -0.0023621000
_diffrn_orient_matrix_UB_32      0.1093785000
_diffrn_orient_matrix_UB_33      0.0060027000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1748
_reflns_number_total             1849
_reflns_odcompleteness_completeness 99.55
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    ?
_refine_diff_density_max         0.968
_refine_diff_density_min         -1.134
_refine_diff_density_rms         0.190
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1849
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.107
_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)+(0.0595P)²+4.8665P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.0980
_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) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C3(H3), C6(H6)
;
_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
Br2 Br 0.41374(6) 0.70344(3) 0.22042(3) 0.01744(17) Uani 1 1 d . . . . .
Br3 Br 0.07712(5) 0.32778(3) 0.52146(3) 0.01694(16) Uani 1 1 d . . . . .
Br1 Br 0.87663(6) 0.42388(3) 0.30298(3) 0.02142(17) Uani 1 1 d . . . . .
N1 N 0.3001(5) 0.4574(2) 0.4140(2) 0.0174(7) Uani 1 1 d . . . . .
H1 H 0.213964 0.424511 0.429648 0.021 Uiso 1 1 calc R . . . .
C5 C 0.4095(5) 0.6005(3) 0.3643(3) 0.0169(9) Uani 1 1 d . . . . .
C4 C 0.2765(6) 0.5471(3) 0.3880(2) 0.0166(9) Uani 1 1 d . . . . .
H4 H 0.168651 0.573133 0.385984 0.020 Uiso 1 1 calc R . . . .
C3 C 0.4499(6) 0.4157(3) 0.4173(2) 0.0162(8) Uani 1 1 d . . . . .
H3 H 0.460782 0.351934 0.435121 0.019 Uiso 1 1 calc R . . . .
C6 C 0.5658(6) 0.5599(3) 0.3682(3) 0.0183(9) Uani 1 1 d . . . . .
H6 H 0.659015 0.596329 0.352942 0.022 Uiso 1 1 calc R . . . .
C2 C 0.5870(5) 0.4668(3) 0.3943(3) 0.0170(9) Uani 1 1 d . . . . .
C7 C 0.3867(6) 0.7008(3) 0.3362(3) 0.0177(9) Uani 1 1 d . . . . .
H7A H 0.469122 0.742917 0.361354 0.021 Uiso 1 1 calc R . . . .
H7B H 0.275550 0.723858 0.350667 0.021 Uiso 1 1 calc R . . . .
C1 C 0.7549(6) 0.4226(3) 0.4023(3) 0.0222(10) Uani 1 1 d . . . . .
H1A H 0.742920 0.356076 0.420605 0.027 Uiso 1 1 calc R . . . .
H1B H 0.818451 0.457880 0.442726 0.027 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
Br2 C7 1.975(4) . ?
Br1 C1 1.953(5) . ?
N1 H1 0.8800 . ?
N1 C4 1.348(5) . ?
N1 C3 1.352(6) . ?
C5 C4 1.376(6) . ?
C5 C6 1.393(6) . ?
C5 C7 1.498(6) . ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.381(6) . ?
C6 H6 0.9500 . ?
C6 C2 1.392(6) . ?
C2 C1 1.505(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?

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
C4 N1 H1 118.4 . . ?
C4 N1 C3 123.1(4) . . ?
C3 N1 H1 118.4 . . ?
C4 C5 C6 118.6(4) . . ?
C4 C5 C7 120.6(4) . . ?
C6 C5 C7 120.8(4) . . ?
N1 C4 C5 119.6(4) . . ?
N1 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N1 C3 H3 120.4 . . ?
N1 C3 C2 119.3(4) . . ?
C2 C3 H3 120.4 . . ?
C5 C6 H6 119.6 . . ?
C2 C6 C5 120.9(4) . . ?
C2 C6 H6 119.6 . . ?
C3 C2 C6 118.5(4) . . ?
C3 C2 C1 119.4(4) . . ?
C6 C2 C1 121.9(4) . . ?
Br2 C7 H7A 110.0 . . ?
Br2 C7 H7B 110.0 . . ?
C5 C7 Br2 108.6(3) . . ?
C5 C7 H7A 110.0 . . ?
C5 C7 H7B 110.0 . . ?
H7A C7 H7B 108.3 . . ?
Br1 C1 H1A 109.2 . . ?
Br1 C1 H1B 109.2 . . ?
C2 C1 Br1 112.2(3) . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?

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 C3 C2 C6 -0.3(6) . . . . ?
N1 C3 C2 C1 176.5(4) . . . . ?
C5 C6 C2 C3 -0.8(7) . . . . ?
C5 C6 C2 C1 -177.5(4) . . . . ?
C4 N1 C3 C2 1.2(6) . . . . ?
C4 C5 C6 C2 1.1(6) . . . . ?
C4 C5 C7 Br2 -106.0(4) . . . . ?
C3 N1 C4 C5 -0.9(6) . . . . ?
C3 C2 C1 Br1 125.6(4) . . . . ?
C6 C5 C4 N1 -0.2(6) . . . . ?
C6 C5 C7 Br2 75.1(5) . . . . ?
C6 C2 C1 Br1 -57.7(5) . . . . ?
C7 C5 C4 N1 -179.1(4) . . . . ?
C7 C5 C6 C2 180.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.650
_oxdiff_exptl_absorpt_empirical_full_min 0.635
####################################################################### 
# 
# 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_DCM_173K
_database_code_depnum_ccdc_archive 'CCDC 2124420'
loop_
_audit_author_name
_audit_author_address
'Shohei Tashiro'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C7 H8 Br2 N, C0.5 H Cl'
_chemical_formula_sum            'C7.50 H9 Br3 Cl N'
_chemical_formula_weight         388.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNBrCl
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   23.3010(2)
_cell_length_b                   11.37880(10)
_cell_length_c                   8.87430(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2352.91(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4592
_cell_measurement_temperature    173
_cell_measurement_theta_max      71.3430
_cell_measurement_theta_min      3.8130
_shelx_estimated_absorpt_T_max   0.671
_shelx_estimated_absorpt_T_min   0.160
_exptl_absorpt_coefficient_mu    14.448
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    2.193
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6224
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.159
_diffrn_reflns_theta_min         3.794
_diffrn_ambient_temperature      173
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  52.00   0.50    0.50    --    0.00  38.00   0.00  156
  2  ω    -37.00  -1.00   0.50    0.50    --    0.00 -38.00 120.00   72
  3  ω     67.00  92.00   0.50    0.50    --   95.70  61.00 -60.00   50
  4  ω     55.00 116.00   0.50    0.50    --   95.70 -82.00-180.00  122
  5  ω     13.00  90.00   0.50    0.50    --   95.70 -45.00-180.00  154
  6  ω     74.00 130.00   0.50    0.50    --   95.70 -77.00-120.00  112
  7  ω     41.00 155.00   0.50    0.50    --   95.70  15.00-180.00  228
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0650775000
_diffrn_orient_matrix_UB_12      0.0218613000
_diffrn_orient_matrix_UB_13      -0.0118430000
_diffrn_orient_matrix_UB_21      -0.0102565000
_diffrn_orient_matrix_UB_22      -0.1331435000
_diffrn_orient_matrix_UB_23      -0.0157797000
_diffrn_orient_matrix_UB_31      -0.0054412000
_diffrn_orient_matrix_UB_32      -0.0107407000
_diffrn_orient_matrix_UB_33      0.1725466000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2104
_reflns_number_total             2268
_reflns_odcompleteness_completeness 99.84
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    ?
_refine_diff_density_max         1.203
_refine_diff_density_min         -1.109
_refine_diff_density_rms         0.161
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.086
_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)+(0.0563P)²+8.7704P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1090
_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) groups
2. Others
 Sof(C1GB)=Sof(H1GC)=Sof(H1GD)=0.5*(1-FVAR(2))
 Sof(C1GA)=Sof(H1GA)=Sof(H1GB)=0.5*FVAR(2)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C1(H1A,H1B), C1GA(H1GA,H1GB), C1GB(H1GC,H1GD)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C6(H6), C3(H3)
;
_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
Br3 Br 0.40854(2) 0.63129(4) 0.36206(5) 0.02763(17) Uani 1 1 d . . . . .
Br2 Br 0.44741(2) 0.17081(4) 0.89485(6) 0.03051(17) Uani 1 1 d . . . . .
Br1 Br 0.23870(2) 0.57609(6) 0.96031(7) 0.0450(2) Uani 1 1 d . . . . .
Cl1G Cl 0.31163(9) 0.2598(3) 0.7004(4) 0.1184(12) Uani 1 1 d . . . . .
N1 N 0.40907(17) 0.5444(3) 0.7040(4) 0.0285(8) Uani 1 1 d . . . . .
H1 H 0.412505 0.570096 0.610881 0.034 Uiso 1 1 calc R . . . .
C5 C 0.44093(19) 0.4188(4) 0.8988(5) 0.0233(9) Uani 1 1 d . . . . .
C4 C 0.44603(19) 0.4626(4) 0.7528(5) 0.0257(9) Uani 1 1 d . . . . .
H4 H 0.475563 0.434698 0.688284 0.031 Uiso 1 1 calc R . . . .
C6 C 0.39785(19) 0.4648(4) 0.9900(5) 0.0244(9) Uani 1 1 d . . . . .
H6 H 0.393734 0.436854 1.090285 0.029 Uiso 1 1 calc R . . . .
C2 C 0.36075(19) 0.5509(4) 0.9366(5) 0.0254(9) Uani 1 1 d . . . . .
C7 C 0.4803(2) 0.3239(4) 0.9505(6) 0.0290(10) Uani 1 1 d . . . . .
H7A H 0.485314 0.328389 1.061111 0.035 Uiso 1 1 calc R . . . .
H7B H 0.518433 0.333541 0.902670 0.035 Uiso 1 1 calc R . . . .
C3 C 0.3676(2) 0.5883(4) 0.7892(5) 0.0280(9) Uani 1 1 d . . . . .
H3 H 0.342365 0.645853 0.748846 0.034 Uiso 1 1 calc R . . . .
C1 C 0.3161(2) 0.6057(5) 1.0354(6) 0.0387(12) Uani 1 1 d . . . . .
H1A H 0.322719 0.691495 1.040613 0.046 Uiso 1 1 calc R . . . .
H1B H 0.319659 0.573537 1.138672 0.046 Uiso 1 1 calc R . . . .
C1GA C 0.250000 0.250000 0.611(2) 0.068(6) Uani 0.62(3) 2 d S T P A 1
H1GA H 0.252626 0.180451 0.544761 0.082 Uiso 0.312(14) 1 calc R . . A 1
H1GB H 0.247374 0.319548 0.544758 0.082 Uiso 0.312(14) 1 calc R . . A 1
C1GB C 0.250000 0.250000 0.769(3) 0.087(12) Uani 0.38(3) 2 d S T P A 2
H1GC H 0.252604 0.181034 0.836466 0.105 Uiso 0.188(14) 1 calc R . . A 2
H1GD H 0.247396 0.318965 0.836469 0.105 Uiso 0.188(14) 1 calc R . . A 2


_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
Br2 C7 1.966(5) . ?
Br1 C1 1.952(5) . ?
Cl1G C1GA 1.642(9) . ?
Cl1G C1GB 1.563(12) . ?
N1 H1 0.8800 . ?
N1 C4 1.340(6) . ?
N1 C3 1.325(6) . ?
C5 C4 1.393(6) . ?
C5 C6 1.392(6) . ?
C5 C7 1.490(6) . ?
C4 H4 0.9500 . ?
C6 H6 0.9500 . ?
C6 C2 1.389(6) . ?
C2 C3 1.386(7) . ?
C2 C1 1.497(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C3 H3 0.9500 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1GA H1GA 0.9900 . ?
C1GA H1GB 0.9900 . ?
C1GB H1GC 0.9900 . ?
C1GB H1GD 0.9900 . ?

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
C4 N1 H1 118.5 . . ?
C3 N1 H1 118.5 . . ?
C3 N1 C4 123.1(4) . . ?
C4 C5 C7 119.6(4) . . ?
C6 C5 C4 117.9(4) . . ?
C6 C5 C7 122.5(4) . . ?
N1 C4 C5 119.7(4) . . ?
N1 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C5 C6 H6 119.5 . . ?
C2 C6 C5 121.0(4) . . ?
C2 C6 H6 119.5 . . ?
C6 C2 C1 121.8(4) . . ?
C3 C2 C6 117.8(4) . . ?
C3 C2 C1 120.3(4) . . ?
Br2 C7 H7A 109.9 . . ?
Br2 C7 H7B 109.9 . . ?
C5 C7 Br2 108.9(3) . . ?
C5 C7 H7A 109.9 . . ?
C5 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
N1 C3 C2 120.5(4) . . ?
N1 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
Br1 C1 H1A 109.3 . . ?
Br1 C1 H1B 109.3 . . ?
C2 C1 Br1 111.8(3) . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 107.9 . . ?
Cl1G C1GA Cl1G 122.6(11) . 2 ?
Cl1G C1GA H1GA 106.7 . . ?
Cl1G C1GA H1GA 106.7 2 . ?
Cl1G C1GA H1GB 106.7 . . ?
Cl1G C1GA H1GB 106.7 2 . ?
H1GA C1GA H1GB 106.6 . . ?
Cl1G C1GB Cl1G 134(2) 2 . ?
Cl1G C1GB H1GC 103.6 2 . ?
Cl1G C1GB H1GC 103.6 . . ?
Cl1G C1GB H1GD 103.6 2 . ?
Cl1G C1GB H1GD 103.6 . . ?
H1GC C1GB H1GD 105.3 . . ?

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
C5 C6 C2 C3 0.8(6) . . . . ?
C5 C6 C2 C1 -176.9(4) . . . . ?
C4 N1 C3 C2 0.3(7) . . . . ?
C4 C5 C6 C2 0.6(6) . . . . ?
C4 C5 C7 Br2 -87.0(5) . . . . ?
C6 C5 C4 N1 -1.6(6) . . . . ?
C6 C5 C7 Br2 91.7(5) . . . . ?
C6 C2 C3 N1 -1.3(7) . . . . ?
C6 C2 C1 Br1 -118.3(4) . . . . ?
C7 C5 C4 N1 177.2(4) . . . . ?
C7 C5 C6 C2 -178.1(4) . . . . ?
C3 N1 C4 C5 1.2(7) . . . . ?
C3 C2 C1 Br1 64.1(5) . . . . ?
C1 C2 C3 N1 176.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.544
_oxdiff_exptl_absorpt_empirical_full_min 0.680
####################################################################### 
# 
# 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_From_CHCl3
_database_code_depnum_ccdc_archive 'CCDC 2124416'
loop_
_audit_author_name
_audit_author_address
'Shohei Tashiro'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C7 H8 Br2 N'
_chemical_formula_sum            'C7 H8 Br3 N'
_chemical_formula_weight         345.87
_chemical_melting_point          ?
_chemical_oxdiff_formula         C7.5H7NBr3
_chemical_oxdiff_usercomment     '1,3-propanesultone-soaking for 30 s'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.1294(2)
_cell_length_b                   14.0393(3)
_cell_length_c                   16.9502(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1934.54(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4148
_cell_measurement_temperature    93
_cell_measurement_theta_max      71.8920
_cell_measurement_theta_min      2.6210
_shelx_estimated_absorpt_T_max   0.467
_shelx_estimated_absorpt_T_min   0.246
_exptl_absorpt_coefficient_mu    14.973
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    2.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5019
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.987
_diffrn_reflns_theta_min         5.219
_diffrn_ambient_temperature      93
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00  -3.00   0.50    0.50    --    0.00 -38.00 -90.00  170
  2  ω      0.00  27.00   0.50    0.50    --    0.00 -38.00 -90.00   54
  3  ω     -3.00  27.00   0.50    0.50    --    0.00  57.00-120.00   60
  4  ω     59.00  92.00   0.50    0.50    --   95.70  82.00-120.00   66
  5  ω     56.00  81.00   0.50    0.50    --   95.70 -61.00-120.00   50
  6  ω      8.00  45.00   0.50    0.50    --   95.70 -61.00-120.00   74
  7  ω    100.00 185.00   0.50    0.50    --   95.70  82.00-120.00  170
  8  ω    117.00 179.00   0.50    0.50    --   95.70  61.00  90.00  124
  9  ω     72.00 146.00   0.50    0.50    --   95.70  45.00-180.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0494739000
_diffrn_orient_matrix_UB_12      0.1016531000
_diffrn_orient_matrix_UB_13      0.0248537000
_diffrn_orient_matrix_UB_21      0.1149425000
_diffrn_orient_matrix_UB_22      0.0412831000
_diffrn_orient_matrix_UB_23      -0.0635990000
_diffrn_orient_matrix_UB_31      -0.1421491000
_diffrn_orient_matrix_UB_32      -0.0021254000
_diffrn_orient_matrix_UB_33      -0.0600668000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1798
_reflns_number_total             1854
_reflns_odcompleteness_completeness 99.95
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         0.688
_refine_diff_density_min         -0.825
_refine_diff_density_rms         0.152
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1854
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0275
_refine_ls_restrained_S_all      1.115
_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)+(0.0388P)²+4.1344P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0728
_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) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C6(H6), C3(H3)
;
_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
Br3 Br 0.07724(4) 0.32784(3) 0.47845(2) 0.01335(12) Uani 1 1 d . . . . .
Br1 Br 0.41379(4) 0.70345(3) 0.77958(2) 0.01425(12) Uani 1 1 d . . . . .
Br2 Br 0.87659(5) 0.42383(3) 0.69703(2) 0.01882(13) Uani 1 1 d . . . . .
N1 N 0.3006(4) 0.4575(2) 0.58571(18) 0.0140(6) Uani 1 1 d . . . . .
H1 H 0.214861 0.424401 0.569795 0.017 Uiso 1 1 calc R . . . .
C2 C 0.4102(4) 0.6010(3) 0.6359(2) 0.0122(7) Uani 1 1 d . . . . .
C4 C 0.4499(4) 0.4160(2) 0.5827(2) 0.0120(7) Uani 1 1 d . . . . .
H4 H 0.460518 0.352222 0.564665 0.014 Uiso 1 1 calc R . . . .
C5 C 0.5879(4) 0.4665(3) 0.6061(2) 0.0131(7) Uani 1 1 d . . . . .
C1 C 0.3862(5) 0.7006(3) 0.6645(2) 0.0162(7) Uani 1 1 d . . . . .
H1A H 0.274642 0.723159 0.650239 0.019 Uiso 1 1 calc R . . . .
H1B H 0.467592 0.743358 0.639256 0.019 Uiso 1 1 calc R . . . .
C6 C 0.5656(5) 0.5600(3) 0.6321(2) 0.0144(7) Uani 1 1 d . . . . .
H6 H 0.658782 0.596337 0.647468 0.017 Uiso 1 1 calc R . . . .
C3 C 0.2758(4) 0.5465(2) 0.6116(2) 0.0142(7) Uani 1 1 d . . . . .
H3 H 0.167778 0.572242 0.613471 0.017 Uiso 1 1 calc R . . . .
C7 C 0.7545(5) 0.4224(3) 0.5977(2) 0.0181(8) Uani 1 1 d . . . . .
H7A H 0.817682 0.457600 0.557160 0.022 Uiso 1 1 calc R . . . .
H7B H 0.742221 0.355780 0.579494 0.022 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
Br1 C1 1.965(4) . ?
Br2 C7 1.955(4) . ?
N1 H1 0.8800 . ?
N1 C4 1.348(5) . ?
N1 C3 1.339(5) . ?
C2 C1 1.494(5) . ?
C2 C6 1.390(5) . ?
C2 C3 1.396(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(5) . ?
C5 C6 1.396(5) . ?
C5 C7 1.496(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C6 H6 0.9500 . ?
C3 H3 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?

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
C4 N1 H1 118.3 . . ?
C3 N1 H1 118.3 . . ?
C3 N1 C4 123.5(3) . . ?
C6 C2 C1 121.5(3) . . ?
C6 C2 C3 118.1(3) . . ?
C3 C2 C1 120.4(3) . . ?
N1 C4 H4 120.1 . . ?
N1 C4 C5 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 117.8(3) . . ?
C4 C5 C7 119.6(3) . . ?
C6 C5 C7 122.4(3) . . ?
Br1 C1 H1A 109.9 . . ?
Br1 C1 H1B 109.9 . . ?
C2 C1 Br1 109.0(2) . . ?
C2 C1 H1A 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
C2 C6 C5 121.5(3) . . ?
C2 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
N1 C3 C2 119.3(3) . . ?
N1 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
Br2 C7 H7A 109.2 . . ?
Br2 C7 H7B 109.2 . . ?
C5 C7 Br2 111.9(3) . . ?
C5 C7 H7A 109.2 . . ?
C5 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?

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 C4 C5 C6 -0.1(5) . . . . ?
N1 C4 C5 C7 -176.0(3) . . . . ?
C4 N1 C3 C2 1.1(5) . . . . ?
C4 C5 C6 C2 1.1(5) . . . . ?
C4 C5 C7 Br2 -126.4(3) . . . . ?
C1 C2 C6 C5 179.4(3) . . . . ?
C1 C2 C3 N1 179.6(3) . . . . ?
C6 C2 C1 Br1 -74.2(4) . . . . ?
C6 C2 C3 N1 -0.1(5) . . . . ?
C6 C5 C7 Br2 57.9(4) . . . . ?
C3 N1 C4 C5 -1.1(5) . . . . ?
C3 C2 C1 Br1 106.2(3) . . . . ?
C3 C2 C6 C5 -1.1(5) . . . . ?
C7 C5 C6 C2 176.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.106
_oxdiff_exptl_absorpt_empirical_full_min 0.440
####################################################################### 
# 
# 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_DCM_178K
_database_code_depnum_ccdc_archive 'CCDC 2124421'
loop_
_audit_author_name
_audit_author_address
'Shohei Tashiro'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C7 H8 Br2 N, C0.5 H Cl'
_chemical_formula_sum            'C7.50 H9 Br3 Cl N'
_chemical_formula_weight         388.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNBrCl
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   23.3004(2)
_cell_length_b                   11.38610(10)
_cell_length_c                   8.87680(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2355.02(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4576
_cell_measurement_temperature    178
_cell_measurement_theta_max      71.9490
_cell_measurement_theta_min      3.8130
_shelx_estimated_absorpt_T_max   0.671
_shelx_estimated_absorpt_T_min   0.160
_exptl_absorpt_coefficient_mu    14.435
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    2.191
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6302
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.259
_diffrn_reflns_theta_min         3.794
_diffrn_ambient_temperature      178
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  52.00   0.50    0.50    --    0.00  38.00   0.00  154
  2  ω    -37.00  -1.00   0.50    0.50    --    0.00 -38.00 120.00   72
  3  ω     67.00  92.00   0.50    0.50    --   95.70  61.00 -60.00   50
  4  ω     52.00 116.00   0.50    0.50    --   95.70 -82.00-180.00  128
  5  ω     13.00  90.00   0.50    0.50    --   95.70 -45.00-180.00  154
  6  ω     74.00 130.00   0.50    0.50    --   95.70 -77.00-120.00  112
  7  ω     41.00 155.00   0.50    0.50    --   95.70  15.00-180.00  228
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0650772000
_diffrn_orient_matrix_UB_12      0.0218966000
_diffrn_orient_matrix_UB_13      -0.0117961000
_diffrn_orient_matrix_UB_21      -0.0102775000
_diffrn_orient_matrix_UB_22      -0.1330499000
_diffrn_orient_matrix_UB_23      -0.0158153000
_diffrn_orient_matrix_UB_31      -0.0054363000
_diffrn_orient_matrix_UB_32      -0.0107519000
_diffrn_orient_matrix_UB_33      0.1724950000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2094
_reflns_number_total             2268
_reflns_odcompleteness_completeness 99.84
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    ?
_refine_diff_density_max         1.163
_refine_diff_density_min         -1.048
_refine_diff_density_rms         0.149
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.062
_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)+(0.0603P)²+6.5856P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1052
_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) groups
2. Others
 Sof(C1GB)=Sof(H1GC)=Sof(H1GD)=0.5*(1-FVAR(2))
 Sof(C1GA)=Sof(H1GA)=Sof(H1GB)=0.5*FVAR(2)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C1(H1A,H1B), C1GA(H1GA,H1GB), C1GB(H1GC,H1GD)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C6(H6), C3(H3)
;
_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
Br3 Br 0.59142(2) 0.36878(4) 0.36216(5) 0.02845(16) Uani 1 1 d . . . . .
Br2 Br 0.55268(2) 0.82904(4) 0.89480(5) 0.03138(16) Uani 1 1 d . . . . .
Br1 Br 0.76125(2) 0.42380(6) 0.96038(6) 0.04639(19) Uani 1 1 d . . . . .
Cl1G Cl 0.68840(8) 0.7375(3) 0.6948(4) 0.1246(12) Uani 1 1 d . . . . .
N1 N 0.59077(16) 0.4558(3) 0.7041(4) 0.0290(8) Uani 1 1 d . . . . .
H1 H 0.587224 0.430013 0.611066 0.035 Uiso 1 1 calc R . . . .
C5 C 0.55901(17) 0.5809(4) 0.8981(5) 0.0243(8) Uani 1 1 d . . . . .
C4 C 0.55392(17) 0.5373(4) 0.7530(5) 0.0258(8) Uani 1 1 d . . . . .
H4 H 0.524383 0.565280 0.688562 0.031 Uiso 1 1 calc R . . . .
C6 C 0.60217(17) 0.5355(4) 0.9894(4) 0.0244(8) Uani 1 1 d . . . . .
H6 H 0.606344 0.564011 1.089429 0.029 Uiso 1 1 calc R . . . .
C2 C 0.63930(18) 0.4491(4) 0.9368(5) 0.0263(8) Uani 1 1 d . . . . .
C7 C 0.51984(19) 0.6764(4) 0.9506(5) 0.0288(9) Uani 1 1 d . . . . .
H7A H 0.515128 0.671869 1.061296 0.035 Uiso 1 1 calc R . . . .
H7B H 0.481594 0.667020 0.903521 0.035 Uiso 1 1 calc R . . . .
C3 C 0.63243(19) 0.4118(4) 0.7891(5) 0.0289(9) Uani 1 1 d . . . . .
H3 H 0.657698 0.354477 0.748507 0.035 Uiso 1 1 calc R . . . .
C1 C 0.6839(2) 0.3942(5) 1.0346(6) 0.0405(11) Uani 1 1 d . . . . .
H1A H 0.677270 0.308342 1.039206 0.049 Uiso 1 1 calc R . . . .
H1B H 0.680309 0.425743 1.138119 0.049 Uiso 1 1 calc R . . . .
C1GA C 0.750000 0.750000 0.611(2) 0.074(6) Uani 0.58(3) 2 d S T P A 1
H1GA H 0.753342 0.680787 0.544415 0.089 Uiso 0.288(13) 1 calc R . . A 1
H1GB H 0.746657 0.819214 0.544417 0.089 Uiso 0.288(13) 1 calc R . . A 1
C1GB C 0.750000 0.750000 0.769(3) 0.093(11) Uani 0.42(3) 2 d S T P A 2
H1GC H 0.753330 0.681051 0.836360 0.112 Uiso 0.212(13) 1 calc R . . A 2
H1GD H 0.746670 0.818950 0.836358 0.112 Uiso 0.212(13) 1 calc R . . A 2


_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
Br2 C7 1.963(4) . ?
Br1 C1 1.949(5) . ?
Cl1G C1GA 1.621(9) . ?
Cl1G C1GB 1.585(11) . ?
N1 H1 0.8800 . ?
N1 C4 1.337(6) . ?
N1 C3 1.327(6) . ?
C5 C4 1.385(6) . ?
C5 C6 1.391(6) . ?
C5 C7 1.495(6) . ?
C4 H4 0.9500 . ?
C6 H6 0.9500 . ?
C6 C2 1.391(6) . ?
C2 C3 1.388(6) . ?
C2 C1 1.492(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C3 H3 0.9500 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1GA H1GA 0.9900 . ?
C1GA H1GB 0.9900 . ?
C1GB H1GC 0.9900 . ?
C1GB H1GD 0.9900 . ?

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
C4 N1 H1 118.4 . . ?
C3 N1 H1 118.4 . . ?
C3 N1 C4 123.1(4) . . ?
C4 C5 C6 118.1(4) . . ?
C4 C5 C7 119.9(4) . . ?
C6 C5 C7 122.0(4) . . ?
N1 C4 C5 119.7(4) . . ?
N1 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C5 C6 H6 119.5 . . ?
C2 C6 C5 121.1(4) . . ?
C2 C6 H6 119.5 . . ?
C6 C2 C1 122.3(4) . . ?
C3 C2 C6 117.5(4) . . ?
C3 C2 C1 120.2(4) . . ?
Br2 C7 H7A 109.9 . . ?
Br2 C7 H7B 109.9 . . ?
C5 C7 Br2 109.1(3) . . ?
C5 C7 H7A 109.9 . . ?
C5 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
N1 C3 C2 120.4(4) . . ?
N1 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
Br1 C1 H1A 109.2 . . ?
Br1 C1 H1B 109.2 . . ?
C2 C1 Br1 112.0(3) . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
Cl1G C1GA Cl1G 125.6(12) 2_665 . ?
Cl1G C1GA H1GA 105.9 2_665 . ?
Cl1G C1GA H1GA 105.9 . . ?
Cl1G C1GA H1GB 105.9 2_665 . ?
Cl1G C1GA H1GB 105.9 . . ?
H1GA C1GA H1GB 106.2 . . ?
Cl1G C1GB Cl1G 130.9(16) . 2_665 ?
Cl1G C1GB H1GC 104.5 . . ?
Cl1G C1GB H1GC 104.5 2_665 . ?
Cl1G C1GB H1GD 104.5 . . ?
Cl1G C1GB H1GD 104.5 2_665 . ?
H1GC C1GB H1GD 105.7 . . ?

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
C5 C6 C2 C3 1.3(6) . . . . ?
C5 C6 C2 C1 -176.6(4) . . . . ?
C4 N1 C3 C2 0.6(7) . . . . ?
C4 C5 C6 C2 0.2(6) . . . . ?
C4 C5 C7 Br2 -86.7(4) . . . . ?
C6 C5 C4 N1 -1.3(6) . . . . ?
C6 C5 C7 Br2 91.5(4) . . . . ?
C6 C2 C3 N1 -1.7(6) . . . . ?
C6 C2 C1 Br1 -117.9(4) . . . . ?
C7 C5 C4 N1 176.9(4) . . . . ?
C7 C5 C6 C2 -178.0(4) . . . . ?
C3 N1 C4 C5 1.0(6) . . . . ?
C3 C2 C1 Br1 64.3(5) . . . . ?
C1 C2 C3 N1 176.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.614
_oxdiff_exptl_absorpt_empirical_full_min 0.670
####################################################################### 
# 
# 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_CD2Cl2_203K
_database_code_depnum_ccdc_archive 'CCDC 2124423'
loop_
_audit_author_name
_audit_author_address
'Shohei Tashiro'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C7 H8 Br2 N, C0.5 H Cl'
_chemical_formula_sum            'C7.50 H8 Br3 Cl N'
_chemical_formula_weight         387.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNBrCl
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   23.3149(5)
_cell_length_b                   11.3966(3)
_cell_length_c                   8.87109(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2357.14(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4184
_cell_measurement_temperature    203
_cell_measurement_theta_max      71.8320
_cell_measurement_theta_min      3.8010
_shelx_estimated_absorpt_T_max   0.532
_shelx_estimated_absorpt_T_min   0.081
_exptl_absorpt_coefficient_mu    14.422
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
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    2.183
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6398
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.118
_diffrn_reflns_theta_min         3.792
_diffrn_ambient_temperature      203
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00 -29.00   0.50    0.50    --    0.00 -38.00-150.00  116
  2  ω     40.00  88.00   0.50    0.50    --    0.00  38.00-120.00   96
  3  ω     59.00 122.00   0.50    0.50    --   95.70 -45.00   0.00  126
  4  ω      9.00  51.00   0.50    0.50    --   95.70 -45.00   0.00   84
  5  ω    106.00 170.00   0.50    0.50    --   95.70  61.00 -60.00  128
  6  ω      6.00 110.00   0.50    0.50    --   95.70 -45.00-180.00  208
  7  ω     99.00 130.00   0.50    0.50    --   95.70  61.00 -90.00   62
  8  ω    111.00 154.00   0.50    0.50    --   95.70  82.00-150.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0599384000
_diffrn_orient_matrix_UB_12      0.0366058000
_diffrn_orient_matrix_UB_13      0.0561261000
_diffrn_orient_matrix_UB_21      0.0025674000
_diffrn_orient_matrix_UB_22      -0.0961411000
_diffrn_orient_matrix_UB_23      0.1216337000
_diffrn_orient_matrix_UB_31      0.0277134000
_diffrn_orient_matrix_UB_32      0.0878002000
_diffrn_orient_matrix_UB_33      0.1103013000
_diffrn_oxdiff_digest_frames     
;
018dc12e3adaca238b7f557e6a88ab35bf00031e7a6
;
_diffrn_oxdiff_digest_hkl        
;
01523e1905464de55b48242eabc11e23c59df4
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2031
_reflns_number_total             2273
_reflns_odcompleteness_completeness 100.00
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_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    ?
_refine_diff_density_max         4.088
_refine_diff_density_min         -2.048
_refine_diff_density_rms         0.362
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0928
_refine_ls_restrained_S_all      1.160
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2594
_refine_ls_wR_factor_ref         0.2658
_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) groups
2. Others
 Sof(C1GA)=Sof(H1GC)=Sof(H1GD)=0.5*(1-FVAR(2))
 Sof(C1GB)=Sof(H1GA)=Sof(H1GB)=0.5*FVAR(2)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7A,H7B), C1GB(H1GA,H1GB), C1GA(H1GC,H1GD)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C6(H6), C3(H3)
;
_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
Br3 Br 0.40868(3) 0.63112(7) -0.13794(8) 0.0310(4) Uani 1 1 d . . . . .
Br2 Br 0.44712(3) 0.17159(7) 0.39482(9) 0.0342(4) Uani 1 1 d . . . . .
Br1 Br 0.23892(4) 0.57622(9) 0.46057(11) 0.0492(4) Uani 1 1 d . . . . .
Cl1G Cl 0.31143(16) 0.2330(5) 0.6839(8) 0.130(2) Uani 1 1 d . . . . .
N1 N 0.4093(3) 0.5443(6) 0.2034(7) 0.0343(14) Uani 1 1 d . . . . .
H1 H 0.412854 0.569730 0.112571 0.041 Uiso 1 1 calc R . . . .
C4 C 0.4461(3) 0.4616(7) 0.2534(9) 0.0312(16) Uani 1 1 d . . . . .
H4 H 0.474642 0.433229 0.189922 0.037 Uiso 1 1 calc R . . . .
C6 C 0.3987(3) 0.4655(6) 0.4896(8) 0.0258(14) Uani 1 1 d . . . . .
H6 H 0.395374 0.438632 0.588213 0.031 Uiso 1 1 calc R . . . .
C5 C 0.4416(3) 0.4195(6) 0.3969(8) 0.0255(15) Uani 1 1 d . . . . .
C2 C 0.3608(3) 0.5513(6) 0.4372(8) 0.0281(14) Uani 1 1 d . . . . .
C3 C 0.3680(3) 0.5877(6) 0.2895(9) 0.0286(14) Uani 1 1 d . . . . .
H3 H 0.343310 0.643868 0.249835 0.034 Uiso 1 1 calc R . . . .
C1 C 0.3163(3) 0.6079(8) 0.5340(10) 0.042(2) Uani 1 1 d . . . . .
H1A H 0.322705 0.692031 0.535755 0.051 Uiso 1 1 calc R . . . .
H1B H 0.319962 0.578945 0.636353 0.051 Uiso 1 1 calc R . . . .
C7 C 0.4806(3) 0.3239(6) 0.4517(9) 0.0318(16) Uani 1 1 d . . . . .
H7A H 0.484682 0.328556 0.560395 0.038 Uiso 1 1 calc R . . . .
H7B H 0.518258 0.332495 0.406654 0.038 Uiso 1 1 calc R . . . .
C1GB C 0.250000 0.250000 0.777(5) 0.24(5) Uani 0.74(5) 2 d S T P A 1
H1GA H 0.254477 0.317740 0.842441 0.293 Uiso 0.37(2) 1 calc R . . A 1
H1GB H 0.245524 0.182260 0.842441 0.293 Uiso 0.37(2) 1 calc R . . A 1
C1GA C 0.250000 0.250000 0.601(5) 0.040(15) Uani 0.26(5) 2 d S T P A 2
H1GC H 0.245542 0.182538 0.534870 0.048 Uiso 0.13(2) 1 calc R . . A 2
H1GD H 0.254458 0.317462 0.534870 0.048 Uiso 0.13(2) 1 calc R . . A 2


_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
Br2 C7 1.969(7) . ?
Br1 C1 1.952(8) . ?
Cl1G C1GB 1.67(2) . ?
Cl1G C1GA 1.624(19) . ?
N1 C4 1.349(10) . ?
N1 C3 1.325(10) . ?
C4 C5 1.365(11) . ?
C6 C5 1.396(10) . ?
C6 C2 1.397(10) . ?
C5 C7 1.500(10) . ?
C2 C3 1.385(11) . ?
C2 C1 1.493(10) . ?

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
C3 N1 C4 122.2(7) . . ?
N1 C4 C5 120.2(7) . . ?
C5 C6 C2 121.3(6) . . ?
C4 C5 C6 118.2(7) . . ?
C4 C5 C7 120.7(7) . . ?
C6 C5 C7 121.0(6) . . ?
C6 C2 C1 123.4(7) . . ?
C3 C2 C6 116.6(6) . . ?
C3 C2 C1 119.9(7) . . ?
N1 C3 C2 121.4(6) . . ?
C2 C1 Br1 111.7(5) . . ?
C5 C7 Br2 108.4(5) . . ?
Cl1G C1GB Cl1G 120(3) . 2 ?
Cl1G C1GA Cl1G 126(3) . 2 ?

_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 5.180
_oxdiff_exptl_absorpt_empirical_full_min 0.236
####################################################################### 
# 
# 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_DCM_223K
_database_code_depnum_ccdc_archive 'CCDC 2124414'
loop_
_audit_author_name
_audit_author_address
'Shohei Tashiro'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C7 H8 Br2 N, C0.5 H Cl'
_chemical_formula_sum            'C7.50 H9 Br3 Cl N'
_chemical_formula_weight         388.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNBrCl
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   23.3051(2)
_cell_length_b                   11.43370(10)
_cell_length_c                   8.89090(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2369.10(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4727
_cell_measurement_temperature    223
_cell_measurement_theta_max      71.6920
_cell_measurement_theta_min      3.7660
_shelx_estimated_absorpt_T_max   0.673
_shelx_estimated_absorpt_T_min   0.161
_exptl_absorpt_coefficient_mu    14.349
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    2.178
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6733
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.212
_diffrn_reflns_theta_min         3.793
_diffrn_ambient_temperature      223
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      9.00  58.00   0.50    0.50    --    0.00  38.00-120.00   98
  2  ω    -28.00  79.00   0.50    0.50    --    0.00  57.00-180.00  214
  3  ω    137.00 185.00   0.50    0.50    --   95.70  45.00 -60.00   96
  4  ω     49.00 119.00   0.50    0.50    --   95.70 -82.00-180.00  140
  5  ω    137.00 174.00   0.50    0.50    --   95.70  45.00 -30.00   74
  6  ω     88.00 185.00   0.50    0.50    --   95.70  45.00 -90.00  194
  7  ω     70.00 125.00   0.50    0.50    --   95.70 -77.00   0.00  110
  8  ω     30.00  62.00   0.50    0.50    --   95.70 -77.00   0.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0650999000
_diffrn_orient_matrix_UB_12      0.0217956000
_diffrn_orient_matrix_UB_13      0.0111741000
_diffrn_orient_matrix_UB_21      0.0102813000
_diffrn_orient_matrix_UB_22      -0.1324705000
_diffrn_orient_matrix_UB_23      0.0159285000
_diffrn_orient_matrix_UB_31      0.0051773000
_diffrn_orient_matrix_UB_32      -0.0107966000
_diffrn_orient_matrix_UB_33      -0.1722326000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2117
_reflns_number_total             2284
_reflns_odcompleteness_completeness 99.88
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    ?
_refine_diff_density_max         1.348
_refine_diff_density_min         -1.400
_refine_diff_density_rms         0.150
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         2284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.072
_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)+(0.0639P)²+8.6131P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1192
_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) groups
2. Others
 Fixed Sof: H1GA(0.5) H1GB(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7A,H7B), C1G(H1GA,H1GB)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C6(H6), C4(H4)
;
_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
Br3 Br 0.40870(2) 0.63091(5) 1.13725(5) 0.03420(18) Uani 1 1 d . . . . .
Br1 Br 0.44667(2) 0.17204(4) 0.60556(6) 0.03777(19) Uani 1 1 d . . . . .
Br2 Br 0.23902(2) 0.57670(7) 0.53904(8) 0.0561(2) Uani 1 1 d . . . . .
Cl1G Cl 0.31138(11) 0.2233(3) 0.3345(4) 0.1142(10) Uani 1 1 d . . . . .
N1 N 0.40941(18) 0.5448(4) 0.7965(5) 0.0344(9) Uani 1 1 d . . . . .
H1 H 0.412882 0.569933 0.888452 0.041 Uiso 1 1 calc R . . . .
C2 C 0.44094(19) 0.4197(4) 0.6025(5) 0.0281(9) Uani 1 1 d . . . . .
C3 C 0.4464(2) 0.4628(4) 0.7470(5) 0.0308(10) Uani 1 1 d . . . . .
H3 H 0.475708 0.435168 0.810331 0.037 Uiso 1 1 calc R . . . .
C6 C 0.3977(2) 0.4645(4) 0.5115(5) 0.0300(9) Uani 1 1 d . . . . .
H6 H 0.393255 0.435803 0.413056 0.036 Uiso 1 1 calc R . . . .
C5 C 0.3609(2) 0.5511(4) 0.5638(5) 0.0311(10) Uani 1 1 d . . . . .
C1 C 0.4800(2) 0.3238(4) 0.5501(6) 0.0327(10) Uani 1 1 d . . . . .
H1A H 0.517811 0.332536 0.596764 0.039 Uiso 1 1 calc R . . . .
H1B H 0.484706 0.328207 0.440693 0.039 Uiso 1 1 calc R . . . .
C4 C 0.3680(2) 0.5890(4) 0.7117(6) 0.0334(10) Uani 1 1 d . . . . .
H4 H 0.343297 0.646162 0.751410 0.040 Uiso 1 1 calc R . . . .
C7 C 0.3164(2) 0.6064(6) 0.4669(7) 0.0482(14) Uani 1 1 d . . . . .
H7A H 0.320060 0.576089 0.364228 0.058 Uiso 1 1 calc R . . . .
H7B H 0.322931 0.690988 0.463514 0.058 Uiso 1 1 calc R . . . .
C1G C 0.250000 0.250000 0.2296(18) 0.150(8) Uani 1 2 d S T P . .
H1GA H 0.257089 0.317606 0.164488 0.180 Uiso 0.5 1 calc R . . . .
H1GB H 0.242911 0.182393 0.164490 0.180 Uiso 0.5 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
Br1 C1 1.964(5) . ?
Br2 C7 1.943(6) . ?
Cl1G C1G 1.735(9) . ?
N1 H1 0.8700 . ?
N1 C3 1.348(6) . ?
N1 C4 1.324(7) . ?
C2 C3 1.382(7) . ?
C2 C6 1.391(7) . ?
C2 C1 1.499(6) . ?
C3 H3 0.9400 . ?
C6 H6 0.9400 . ?
C6 C5 1.390(7) . ?
C5 C4 1.394(7) . ?
C5 C7 1.491(7) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C4 H4 0.9400 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C1G H1GA 0.9800 . ?
C1G H1GB 0.9800 . ?

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
C3 N1 H1 118.5 . . ?
C4 N1 H1 118.5 . . ?
C4 N1 C3 123.0(4) . . ?
C3 C2 C6 118.4(4) . . ?
C3 C2 C1 119.7(4) . . ?
C6 C2 C1 121.9(4) . . ?
N1 C3 C2 119.6(4) . . ?
N1 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C2 C6 H6 119.5 . . ?
C5 C6 C2 120.9(4) . . ?
C5 C6 H6 119.5 . . ?
C6 C5 C4 117.7(4) . . ?
C6 C5 C7 122.5(5) . . ?
C4 C5 C7 119.7(5) . . ?
Br1 C1 H1A 109.8 . . ?
Br1 C1 H1B 109.8 . . ?
C2 C1 Br1 109.2(3) . . ?
C2 C1 H1A 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.3 . . ?
N1 C4 C5 120.3(4) . . ?
N1 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
Br2 C7 H7A 109.1 . . ?
Br2 C7 H7B 109.1 . . ?
C5 C7 Br2 112.4(4) . . ?
C5 C7 H7A 109.1 . . ?
C5 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
Cl1G C1G Cl1G 115.0(9) 2 . ?
Cl1G C1G H1GA 108.5 2 . ?
Cl1G C1G H1GA 108.5 . . ?
Cl1G C1G H1GB 108.5 2 . ?
Cl1G C1G H1GB 108.5 . . ?
H1GA C1G H1GB 107.5 . . ?

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
C2 C6 C5 C4 -1.6(7) . . . . ?
C2 C6 C5 C7 176.3(5) . . . . ?
C3 N1 C4 C5 0.1(7) . . . . ?
C3 C2 C6 C5 0.3(7) . . . . ?
C3 C2 C1 Br1 86.9(5) . . . . ?
C6 C2 C3 N1 1.2(7) . . . . ?
C6 C2 C1 Br1 -90.9(5) . . . . ?
C6 C5 C4 N1 1.5(7) . . . . ?
C6 C5 C7 Br2 116.9(5) . . . . ?
C1 C2 C3 N1 -176.7(4) . . . . ?
C1 C2 C6 C5 178.2(4) . . . . ?
C4 N1 C3 C2 -1.5(7) . . . . ?
C4 C5 C7 Br2 -65.2(6) . . . . ?
C7 C5 C4 N1 -176.5(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.359
_oxdiff_exptl_absorpt_empirical_full_min 0.642
####################################################################### 
# 
# 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_II_293K
_database_code_depnum_ccdc_archive 'CCDC 2125695'
loop_
_audit_author_name
_audit_author_address
'Shohei Tashiro'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2021-12-02 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_date             2021-12-02
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C7 H8 Br2 N'
_chemical_formula_sum            'C7 H8 Br3 N'
_chemical_formula_weight         345.87
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNBr
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.16082(19)
_cell_length_b                   14.2650(3)
_cell_length_c                   17.0946(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1990.05(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3481
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.6190
_cell_measurement_theta_min      5.1560
_shelx_estimated_absorpt_T_max   0.548
_shelx_estimated_absorpt_T_min   0.108
_exptl_absorpt_coefficient_mu    14.555
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
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    2.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.047
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5668
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.164
_diffrn_reflns_theta_min         5.175
_diffrn_ambient_temperature      293.0
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     12.00  88.00   0.50    0.50    --    0.00  38.00  30.00  152
  2  ω      7.00  62.00   0.50    0.50    --    0.00  38.00 -60.00  110
  3  ω     36.00 122.00   0.50    0.64    --   95.70 -45.00  60.00  172
  4  ω     39.00  92.00   0.50    0.64    --   95.70 -61.00 -90.00  106
  5  ω    144.00 170.00   0.50    0.64    --   95.70  45.00-120.00   52
  6  ω     20.00 112.00   0.50    0.64    --   95.70 -61.00-180.00  184
  7  ω     69.00 164.00   0.50    0.64    --   95.70  61.00 -90.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0974303000
_diffrn_orient_matrix_UB_12      0.0924061000
_diffrn_orient_matrix_UB_13      0.0034088000
_diffrn_orient_matrix_UB_21      0.0756504000
_diffrn_orient_matrix_UB_22      0.0300640000
_diffrn_orient_matrix_UB_23      -0.0786572000
_diffrn_orient_matrix_UB_31      -0.1430246000
_diffrn_orient_matrix_UB_32      -0.0469586000
_diffrn_orient_matrix_UB_33      -0.0438807000
_diffrn_oxdiff_digest_frames     
;
017732b6c948ee9d383b686bb731f1d47b000318c28
;
_diffrn_oxdiff_digest_hkl        
;
01fa6351ab9ce6167313aafa7bf972ede0d5ba
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1694
_reflns_number_total             1920
_reflns_odcompleteness_completeness 99.95
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_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    ?
_refine_diff_density_max         1.575
_refine_diff_density_min         -1.255
_refine_diff_density_rms         0.209
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1920
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0568
_refine_ls_restrained_S_all      1.100
_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)+(0.1066P)²+2.6857P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1648
_refine_ls_wR_factor_ref         0.1694
_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) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C3(H3), C6(H6)
;
_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
Br3 Br 0.92234(7) 0.32988(5) 0.52307(4) 0.0403(3) Uani 1 1 d . . . . .
Br1 Br 0.58570(8) 0.69624(5) 0.22410(4) 0.0434(3) Uani 1 1 d . . . . .
Br2 Br 0.12582(11) 0.41863(6) 0.30268(5) 0.0597(3) Uani 1 1 d . . . . .
N1 N 0.6944(6) 0.4546(4) 0.4160(3) 0.0411(12) Uani 1 1 d . . . . .
H1 H 0.778004 0.423334 0.432160 0.049 Uiso 1 1 calc R . . . .
C5 C 0.4127(7) 0.4620(5) 0.3939(4) 0.0358(13) Uani 1 1 d . . . . .
C4 C 0.5482(8) 0.4123(4) 0.4174(4) 0.0388(13) Uani 1 1 d . . . . .
H4 H 0.538356 0.350485 0.434075 0.047 Uiso 1 1 calc R . . . .
C3 C 0.7189(7) 0.5422(4) 0.3911(4) 0.0392(13) Uani 1 1 d . . . . .
H3 H 0.823785 0.567693 0.391037 0.047 Uiso 1 1 calc R . . . .
C2 C 0.5872(7) 0.5949(5) 0.3655(3) 0.0354(13) Uani 1 1 d . . . . .
C6 C 0.4324(7) 0.5538(5) 0.3676(4) 0.0364(13) Uani 1 1 d . . . . .
H6 H 0.341500 0.587979 0.351395 0.044 Uiso 1 1 calc R . . . .
C1 C 0.6104(9) 0.6929(5) 0.3379(4) 0.0454(15) Uani 1 1 d . . . . .
H1A H 0.718660 0.714945 0.352446 0.054 Uiso 1 1 calc R . . . .
H1B H 0.529833 0.733540 0.362175 0.054 Uiso 1 1 calc R . . . .
C7 C 0.2465(9) 0.4170(6) 0.4000(5) 0.0557(19) Uani 1 1 d . . . . .
H7A H 0.183301 0.449597 0.439622 0.067 Uiso 1 1 calc R . . . .
H7B H 0.259752 0.352579 0.416910 0.067 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
Br1 C1 1.957(7) . ?
Br2 C7 1.933(8) . ?
N1 C4 1.338(9) . ?
N1 C3 1.336(8) . ?
C5 C4 1.373(9) . ?
C5 C6 1.395(9) . ?
C5 C7 1.503(8) . ?
C3 C2 1.382(9) . ?
C2 C6 1.392(9) . ?
C2 C1 1.488(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
C3 N1 C4 124.1(5) . . ?
C4 C5 C6 119.1(5) . . ?
C4 C5 C7 119.1(6) . . ?
C6 C5 C7 121.8(6) . . ?
N1 C4 C5 118.7(6) . . ?
N1 C3 C2 119.6(6) . . ?
C3 C2 C6 118.0(6) . . ?
C3 C2 C1 120.8(6) . . ?
C6 C2 C1 121.3(6) . . ?
C2 C6 C5 120.5(6) . . ?
C2 C1 Br1 109.0(5) . . ?
C5 C7 Br2 113.2(5) . . ?

_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 4.624
_oxdiff_exptl_absorpt_empirical_full_min 0.374
####################################################################### 
# 
# 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_DBM_223K
_database_code_depnum_ccdc_archive 'CCDC 2124422'
loop_
_audit_author_name
_audit_author_address
'Shohei Tashiro'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C7 H8 Br2 N, C0.5 H Br'
_chemical_formula_sum            'C7.50 H9 Br4 N'
_chemical_formula_weight         432.80
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNBr
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   23.6012(4)
_cell_length_b                   11.3363(2)
_cell_length_c                   8.94002(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2391.89(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4045
_cell_measurement_temperature    223
_cell_measurement_theta_max      71.7790
_cell_measurement_theta_min      3.7560
_shelx_estimated_absorpt_T_max   0.739
_shelx_estimated_absorpt_T_min   0.086
_exptl_absorpt_coefficient_mu    16.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
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    2.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1608
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7159
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.963
_diffrn_reflns_theta_min         3.746
_diffrn_ambient_temperature      223
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  14.00   0.50    0.50    --    0.00  77.00-180.00   52
  2  ω    -27.00  47.00   0.50    0.50    --    0.00  38.00  60.00  148
  3  ω     50.00  75.00   0.50    0.50    --    0.00  77.00-180.00   50
  4  ω     67.00 176.00   0.50    1.45    --   95.70  30.00 120.00  218
  5  ω     55.00 126.00   0.50    1.45    --   95.70 -82.00 -60.00  142
  6  ω     26.00 125.00   0.50    1.45    --   95.70 -61.00 -60.00  198
  7  ω     96.00 122.00   0.50    1.45    --   95.70 -82.00 -30.00   52
  8  ω     14.00  72.00   0.50    1.45    --   95.70 -15.00 150.00  116
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0538459000
_diffrn_orient_matrix_UB_12      -0.0763538000
_diffrn_orient_matrix_UB_13      0.0102100000
_diffrn_orient_matrix_UB_21      0.0369059000
_diffrn_orient_matrix_UB_22      -0.1117103000
_diffrn_orient_matrix_UB_23      0.0114390000
_diffrn_orient_matrix_UB_31      0.0007490000
_diffrn_orient_matrix_UB_32      0.0120683000
_diffrn_orient_matrix_UB_33      0.1716764000
_diffrn_oxdiff_digest_frames     
;
0142ca16b7ff93d92f46a9b4a58b34f3af00031443f
;
_diffrn_oxdiff_digest_hkl        
;
01a091da3ea71b613d82c8e7f3fd0b072c8186
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2100
_reflns_number_total             2314
_reflns_odcompleteness_completeness 99.76
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_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    ?
_refine_diff_density_max         0.807
_refine_diff_density_min         -0.757
_refine_diff_density_rms         0.147
_refine_ls_extinction_coef       0.00043(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         2314
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0554P)²+1.7451P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0953
_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) groups
2. Others
 Fixed Sof: H1GA(0.5) H1GB(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7A,H7B), C1G(H1GA,H1GB)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C6(H6), C4(H4)
;
_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
Br3 Br 0.59172(2) 0.62877(4) 0.35955(4) 0.03120(16) Uani 1 1 d . . . . .
Br1 Br 0.54964(2) 0.17327(4) 0.89336(5) 0.03299(16) Uani 1 1 d . . . . .
Br2 Br 0.75868(2) 0.57376(5) 0.95551(6) 0.04685(18) Uani 1 1 d . . . . .
Br1G Br 0.68246(2) 0.24553(6) 0.72397(7) 0.0588(2) Uani 1 1 d . . . . .
N1 N 0.59077(15) 0.5433(3) 0.6990(4) 0.0312(7) Uani 1 1 d . . . . .
H1 H 0.587748 0.567141 0.608004 0.037 Uiso 1 1 calc R . . . .
C2 C 0.55840(16) 0.4220(3) 0.8951(4) 0.0243(8) Uani 1 1 d . . . . .
C3 C 0.55379(17) 0.4626(4) 0.7492(5) 0.0300(8) Uani 1 1 d . . . . .
H3 H 0.525358 0.434187 0.686804 0.036 Uiso 1 1 calc R . . . .
C5 C 0.63812(16) 0.5533(3) 0.9310(4) 0.0261(8) Uani 1 1 d . . . . .
C6 C 0.60077(16) 0.4685(3) 0.9863(4) 0.0256(7) Uani 1 1 d . . . . .
H6 H 0.604155 0.442783 1.084668 0.031 Uiso 1 1 calc R . . . .
C1 C 0.51861(18) 0.3284(3) 0.9483(5) 0.0306(8) Uani 1 1 d . . . . .
H1A H 0.481702 0.339184 0.902587 0.037 Uiso 1 1 calc R . . . .
H1B H 0.514211 0.333562 1.055998 0.037 Uiso 1 1 calc R . . . .
C4 C 0.63174(18) 0.5878(4) 0.7831(5) 0.0312(9) Uani 1 1 d . . . . .
H4 H 0.656534 0.642978 0.742504 0.037 Uiso 1 1 calc R . . . .
C7 C 0.68200(18) 0.6091(4) 1.0272(5) 0.0384(10) Uani 1 1 d . . . . .
H7A H 0.677882 0.580650 1.128919 0.046 Uiso 1 1 calc R . . . .
H7B H 0.676392 0.693870 1.028017 0.046 Uiso 1 1 calc R . . . .
C1G C 0.750000 0.250000 0.6068(8) 0.0528(18) Uani 1 2 d S T P . .
H1GA H 0.748945 0.319068 0.542814 0.063 Uiso 0.5 1 calc R . . . .
H1GB H 0.751054 0.180931 0.542815 0.063 Uiso 0.5 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
Br1 C1 1.968(4) . ?
Br2 C7 1.961(4) . ?
Br1G C1G 1.908(4) . ?
N1 C3 1.341(5) . ?
N1 C4 1.325(6) . ?
C2 C3 1.388(6) . ?
C2 C6 1.394(5) . ?
C2 C1 1.494(5) . ?
C5 C6 1.395(5) . ?
C5 C4 1.387(6) . ?
C5 C7 1.487(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
C4 N1 C3 123.0(3) . . ?
C3 C2 C6 118.7(4) . . ?
C3 C2 C1 119.1(4) . . ?
C6 C2 C1 122.2(4) . . ?
N1 C3 C2 119.3(4) . . ?
C6 C5 C7 121.9(4) . . ?
C4 C5 C6 117.6(4) . . ?
C4 C5 C7 120.4(4) . . ?
C2 C6 C5 120.5(4) . . ?
C2 C1 Br1 108.7(3) . . ?
N1 C4 C5 120.8(4) . . ?
C5 C7 Br2 111.5(3) . . ?
Br1G C1G Br1G 113.4(4) . 2_655 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.021
_oxdiff_exptl_absorpt_empirical_full_min 0.332
####################################################################### 
# 
# 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_DCM_188K
_database_code_depnum_ccdc_archive 'CCDC 2124413'
loop_
_audit_author_name
_audit_author_address
'Shohei Tashiro'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C7 H8 Br2 N, C0.5 H Cl'
_chemical_formula_sum            'C7.50 H9 Br3 Cl N'
_chemical_formula_weight         388.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNBrCl
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   23.3000(2)
_cell_length_b                   11.40130(10)
_cell_length_c                   8.88100(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2359.24(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4936
_cell_measurement_temperature    188
_cell_measurement_theta_max      71.7910
_cell_measurement_theta_min      3.8050
_shelx_estimated_absorpt_T_max   0.672
_shelx_estimated_absorpt_T_min   0.161
_exptl_absorpt_coefficient_mu    14.409
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    2.187
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6918
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.994
_diffrn_reflns_theta_min         3.794
_diffrn_ambient_temperature      188
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  85.00   0.50    0.50    --    0.00  77.00 -60.00  238
  2  ω      8.00  33.00   0.50    0.50    --    0.00  57.00 -90.00   50
  3  ω     53.00 119.00   0.50    0.50    --   95.70 -82.00-180.00  132
  4  ω     90.00 121.00   0.50    0.50    --   95.70 -30.00   0.00   62
  5  ω     56.00  84.00   0.50    0.50    --   95.70 -61.00-180.00   56
  6  ω      7.00  52.00   0.50    0.50    --   95.70 -61.00-180.00   90
  7  ω     23.00  76.00   0.50    0.50    --   95.70 -30.00   0.00  106
  8  ω     88.00 116.00   0.50    0.50    --   95.70 -61.00-180.00   56
  9  ω     16.00 126.00   0.50    0.50    --   95.70 -30.00-120.00  220
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0650691000
_diffrn_orient_matrix_UB_12      -0.0218568000
_diffrn_orient_matrix_UB_13      0.0118570000
_diffrn_orient_matrix_UB_21      -0.0102754000
_diffrn_orient_matrix_UB_22      0.1328876000
_diffrn_orient_matrix_UB_23      0.0158778000
_diffrn_orient_matrix_UB_31      -0.0054929000
_diffrn_orient_matrix_UB_32      0.0107282000
_diffrn_orient_matrix_UB_33      -0.1723984000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2131
_reflns_number_total             2277
_reflns_odcompleteness_completeness 99.92
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    ?
_refine_diff_density_max         2.166
_refine_diff_density_min         -1.367
_refine_diff_density_rms         0.195
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0542
_refine_ls_restrained_S_all      1.101
_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)+(0.1017P)²+8.7525P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1556
_refine_ls_wR_factor_ref         0.1577
_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) groups
2. Others
 Sof(C1GA)=Sof(H1GC)=Sof(H1GD)=0.5*(1-FVAR(2))
 Sof(C1GB)=Sof(H1GA)=Sof(H1GB)=0.5*FVAR(2)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7A,H7B), C1GB(H1GA,H1GB), C1GA(H1GC,H1GD)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C6(H6), C4(H4)
;
_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
Br3 Br 0.40864(2) 0.36886(5) -0.13755(6) 0.0309(2) Uani 1 1 d . . . . .
Br1 Br 0.44710(3) 0.82877(5) 0.39475(7) 0.0340(2) Uani 1 1 d . . . . .
Br2 Br 0.23885(3) 0.42339(7) 0.46056(9) 0.0501(3) Uani 1 1 d . . . . .
Cl1G Cl 0.31147(12) 0.7683(4) 0.6843(6) 0.1300(16) Uani 1 1 d . . . . .
N1 N 0.4092(2) 0.4558(4) 0.2033(5) 0.0316(10) Uani 1 1 d . . . . .
H1 H 0.412593 0.430606 0.110042 0.038 Uiso 1 1 calc R . . . .
C2 C 0.4412(2) 0.5810(5) 0.3974(6) 0.0257(11) Uani 1 1 d . . . . .
C3 C 0.4461(2) 0.5373(5) 0.2531(6) 0.0283(11) Uani 1 1 d . . . . .
H3 H 0.475741 0.564970 0.188832 0.034 Uiso 1 1 calc R . . . .
C6 C 0.3977(2) 0.5353(5) 0.4890(6) 0.0279(11) Uani 1 1 d . . . . .
H6 H 0.393403 0.563918 0.588872 0.033 Uiso 1 1 calc R . . . .
C5 C 0.3609(2) 0.4492(5) 0.4367(6) 0.0292(11) Uani 1 1 d . . . . .
C1 C 0.4803(2) 0.6763(5) 0.4504(7) 0.0307(12) Uani 1 1 d . . . . .
H1A H 0.518551 0.667276 0.403458 0.037 Uiso 1 1 calc R . . . .
H1B H 0.484915 0.671636 0.561065 0.037 Uiso 1 1 calc R . . . .
C4 C 0.3676(2) 0.4115(5) 0.2891(7) 0.0306(11) Uani 1 1 d . . . . .
H4 H 0.342508 0.353719 0.249120 0.037 Uiso 1 1 calc R . . . .
C7 C 0.3159(3) 0.3936(7) 0.5348(8) 0.0434(15) Uani 1 1 d . . . . .
H7A H 0.319412 0.424839 0.638355 0.052 Uiso 1 1 calc R . . . .
H7B H 0.322502 0.307896 0.538905 0.052 Uiso 1 1 calc R . . . .
C1GB C 0.250000 0.750000 0.768(3) 0.109(13) Uani 0.56(4) 2 d S T P A 1
H1GA H 0.245092 0.818740 0.835171 0.131 Uiso 0.28(2) 1 calc R . . A 1
H1GB H 0.254908 0.681263 0.835176 0.131 Uiso 0.28(2) 1 calc R . . A 1
C1GA C 0.250000 0.750000 0.611(4) 0.091(14) Uani 0.44(4) 2 d S T P A 2
H1GC H 0.245113 0.818447 0.543312 0.109 Uiso 0.22(2) 1 calc R . . A 2
H1GD H 0.254887 0.681556 0.543306 0.109 Uiso 0.22(2) 1 calc R . . A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.965(6) . ?
Br2 C7 1.942(6) . ?
Cl1G C1GB 1.628(15) . ?
Cl1G C1GA 1.588(16) . ?
N1 H1 0.8800 . ?
N1 C3 1.341(7) . ?
N1 C4 1.332(8) . ?
C2 C3 1.380(8) . ?
C2 C6 1.401(8) . ?
C2 C1 1.493(8) . ?
C3 H3 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.385(8) . ?
C5 C4 1.388(8) . ?
C5 C7 1.503(8) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C4 H4 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C1GB H1GA 0.9900 . ?
C1GB H1GB 0.9900 . ?
C1GA H1GC 0.9900 . ?
C1GA H1GD 0.9900 . ?

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
C3 N1 H1 118.7 . . ?
C4 N1 H1 118.7 . . ?
C4 N1 C3 122.7(5) . . ?
C3 C2 C6 117.7(5) . . ?
C3 C2 C1 120.4(5) . . ?
C6 C2 C1 121.9(5) . . ?
N1 C3 C2 120.3(5) . . ?
N1 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C2 C6 H6 119.4 . . ?
C5 C6 C2 121.2(5) . . ?
C5 C6 H6 119.4 . . ?
C6 C5 C4 117.8(5) . . ?
C6 C5 C7 122.5(5) . . ?
C4 C5 C7 119.7(5) . . ?
Br1 C1 H1A 109.9 . . ?
Br1 C1 H1B 109.9 . . ?
C2 C1 Br1 108.9(4) . . ?
C2 C1 H1A 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
N1 C4 C5 120.4(5) . . ?
N1 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
Br2 C7 H7A 109.2 . . ?
Br2 C7 H7B 109.2 . . ?
C5 C7 Br2 112.0(4) . . ?
C5 C7 H7A 109.2 . . ?
C5 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
Cl1G C1GB Cl1G 125(2) . 2_565 ?
Cl1G C1GB H1GA 106.0 . . ?
Cl1G C1GB H1GA 106.0 2_565 . ?
Cl1G C1GB H1GB 106.0 . . ?
Cl1G C1GB H1GB 106.0 2_565 . ?
H1GA C1GB H1GB 106.3 . . ?
Cl1G C1GA Cl1G 131(3) 2_565 . ?
Cl1G C1GA H1GC 104.4 2_565 . ?
Cl1G C1GA H1GC 104.4 . . ?
Cl1G C1GA H1GD 104.4 2_565 . ?
Cl1G C1GA H1GD 104.4 . . ?
H1GC C1GA H1GD 105.6 . . ?

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
C2 C6 C5 C4 -1.4(8) . . . . ?
C2 C6 C5 C7 176.5(5) . . . . ?
C3 N1 C4 C5 0.1(8) . . . . ?
C3 C2 C6 C5 0.0(8) . . . . ?
C3 C2 C1 Br1 86.8(5) . . . . ?
C6 C2 C3 N1 1.5(8) . . . . ?
C6 C2 C1 Br1 -91.4(5) . . . . ?
C6 C5 C4 N1 1.4(8) . . . . ?
C6 C5 C7 Br2 117.6(5) . . . . ?
C1 C2 C3 N1 -176.7(5) . . . . ?
C1 C2 C6 C5 178.2(5) . . . . ?
C4 N1 C3 C2 -1.6(8) . . . . ?
C4 C5 C7 Br2 -64.5(7) . . . . ?
C7 C5 C4 N1 -176.6(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.473
_oxdiff_exptl_absorpt_empirical_full_min 0.642
####################################################################### 
# 
# 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_DBM_293K
_database_code_depnum_ccdc_archive 'CCDC 2124429'
loop_
_audit_author_name
_audit_author_address
'Shohei Tashiro'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C7 H8 Br2 N, C0.5 H Br'
_chemical_formula_sum            'C7.50 H9 Br4 N'
_chemical_formula_weight         432.80
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNBr
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   23.7150(8)
_cell_length_b                   11.4034(4)
_cell_length_c                   8.9608(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2423.28(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3663
_cell_measurement_temperature    293
_cell_measurement_theta_max      71.5050
_cell_measurement_theta_min      3.7260
_shelx_estimated_absorpt_T_max   0.742
_shelx_estimated_absorpt_T_min   0.087
_exptl_absorpt_coefficient_mu    15.864
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.02124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
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    2.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1608
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6687
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.856
_diffrn_reflns_theta_min         3.728
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      7.00  38.00   0.50    0.50    --    0.00  57.00  90.00   62
  2  ω    -25.00  52.00   0.50    0.50    --    0.00  38.00  60.00  154
  3  ω     51.00 130.00   0.50    1.35    --   95.70 -82.00 -60.00  158
  4  ω     84.00 184.00   0.50    1.35    --   95.70  61.00-150.00  200
  5  ω     19.00  70.00   0.50    1.35    --   95.70 -82.00 -30.00  102
  6  ω     97.00 131.00   0.50    1.35    --   95.70 -82.00 -30.00   68
  7  ω     69.00 181.00   0.50    1.35    --   95.70  45.00 -30.00  224
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0562289000
_diffrn_orient_matrix_UB_12      -0.0678684000
_diffrn_orient_matrix_UB_13      0.0046762000
_diffrn_orient_matrix_UB_21      0.0326078000
_diffrn_orient_matrix_UB_22      -0.1168514000
_diffrn_orient_matrix_UB_23      -0.0019540000
_diffrn_orient_matrix_UB_31      0.0018815000
_diffrn_orient_matrix_UB_32      0.0004256000
_diffrn_orient_matrix_UB_33      0.1717147000
_diffrn_oxdiff_digest_frames     
;
0177b8a7bd239a48e0a39c8b091c51afcd00029a66c
;
_diffrn_oxdiff_digest_hkl        
;
01e0d27c7a5ead109a319fe7f3f511524c8cb1
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1895
_reflns_number_total             2331
_reflns_odcompleteness_completeness 99.00
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_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    ?
_refine_diff_density_max         1.241
_refine_diff_density_min         -1.010
_refine_diff_density_rms         0.204
_refine_ls_extinction_coef       0.00029(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         2331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0576
_refine_ls_restrained_S_all      1.131
_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)+(0.1374P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1785
_refine_ls_wR_factor_ref         0.2082
_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) groups
2. Others
 Fixed Sof: H1GA(0.5) H1GB(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7A,H7B), C1G(H1GA,H1GB)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C6(H6), C4(H4)
;
_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
Br3 Br 0.59163(3) 0.37192(7) 0.64059(9) 0.0496(3) Uani 1 1 d . . . . .
Br1 Br 0.54985(4) 0.82508(7) 0.10740(10) 0.0516(4) Uani 1 1 d . . . . .
Br2 Br 0.75790(4) 0.42618(10) 0.04541(12) 0.0704(4) Uani 1 1 d . . . . .
Br1G Br 0.68287(5) 0.75422(13) 0.27724(16) 0.0887(5) Uani 1 1 d . . . . .
N1 N 0.5900(3) 0.4568(6) 0.3015(7) 0.0474(15) Uani 1 1 d . . . . .
H1 H 0.586726 0.433159 0.392193 0.057 Uiso 1 1 calc R . . . .
C3 C 0.5539(3) 0.5365(7) 0.2514(8) 0.0462(17) Uani 1 1 d . . . . .
H3 H 0.525863 0.565243 0.314045 0.055 Uiso 1 1 calc R . . . .
C6 C 0.6006(3) 0.5304(6) 0.0171(8) 0.0379(14) Uani 1 1 d . . . . .
H6 H 0.604240 0.555916 -0.080998 0.045 Uiso 1 1 calc R . . . .
C2 C 0.5580(3) 0.5773(6) 0.1055(8) 0.0407(15) Uani 1 1 d . . . . .
C5 C 0.6379(3) 0.4466(6) 0.0709(8) 0.0429(15) Uani 1 1 d . . . . .
C4 C 0.6311(4) 0.4116(7) 0.2172(9) 0.0485(18) Uani 1 1 d . . . . .
H4 H 0.655365 0.355918 0.257653 0.058 Uiso 1 1 calc R . . . .
C1 C 0.5194(3) 0.6705(6) 0.0535(9) 0.0456(16) Uani 1 1 d . . . . .
H1A H 0.482594 0.660171 0.098900 0.055 Uiso 1 1 calc R . . . .
H1B H 0.514971 0.665488 -0.053938 0.055 Uiso 1 1 calc R . . . .
C7 C 0.6813(3) 0.3913(9) -0.0248(10) 0.059(2) Uani 1 1 d . . . . .
H7A H 0.677083 0.419566 -0.126321 0.071 Uiso 1 1 calc R . . . .
H7B H 0.675718 0.307095 -0.025565 0.071 Uiso 1 1 calc R . . . .
C1G C 0.750000 0.750000 0.3960(18) 0.077(4) Uani 1 2 d S T P . .
H1GA H 0.749001 0.681284 0.459719 0.093 Uiso 0.5 1 calc R . . . .
H1GB H 0.750999 0.818715 0.459720 0.093 Uiso 0.5 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
Br1 C1 1.965(7) . ?
Br2 C7 1.962(8) . ?
Br1G C1G 1.915(9) . ?
N1 C3 1.326(10) . ?
N1 C4 1.337(11) . ?
C3 C2 1.391(11) . ?
C6 C2 1.392(10) . ?
C6 C5 1.389(10) . ?
C2 C1 1.478(11) . ?
C5 C4 1.380(12) . ?
C5 C7 1.480(11) . ?

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
C3 N1 C4 123.0(7) . . ?
N1 C3 C2 120.2(7) . . ?
C5 C6 C2 122.0(7) . . ?
C3 C2 C6 117.2(7) . . ?
C3 C2 C1 119.6(7) . . ?
C6 C2 C1 123.2(7) . . ?
C6 C5 C7 122.3(7) . . ?
C4 C5 C6 117.0(7) . . ?
C4 C5 C7 120.6(7) . . ?
N1 C4 C5 120.7(7) . . ?
C2 C1 Br1 109.9(5) . . ?
C5 C7 Br2 111.8(5) . . ?
Br1G C1G Br1G 112.5(8) . 2_665 ?

_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 17.552
_oxdiff_exptl_absorpt_empirical_full_min 0.387
####################################################################### 
# 
# 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_CD2Cl2_198K
_database_code_depnum_ccdc_archive 'CCDC 2124426'
loop_
_audit_author_name
_audit_author_address
'Shohei Tashiro'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C7 H8 Br2 N, C0.5 H Cl'
_chemical_formula_sum            'C7.50 H9 Br3 Cl N'
_chemical_formula_weight         388.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNBrCl
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   23.3143(4)
_cell_length_b                   11.3889(2)
_cell_length_c                   8.8730(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2356.00(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4620
_cell_measurement_temperature    198
_cell_measurement_theta_max      71.9010
_cell_measurement_theta_min      3.7940
_shelx_estimated_absorpt_T_max   0.532
_shelx_estimated_absorpt_T_min   0.081
_exptl_absorpt_coefficient_mu    14.429
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.12609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
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    2.190
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6583
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.216
_diffrn_reflns_theta_min         3.792
_diffrn_ambient_temperature      198
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     40.00  88.00   0.50    0.50    --    0.00  38.00-120.00   96
  2  ω    -87.00 -29.00   0.50    0.50    --    0.00 -38.00-150.00  116
  3  ω      7.00 120.00   0.50    0.50    --   95.70 -45.00  30.00  226
  4  ω      6.00 122.00   0.50    0.50    --   95.70 -61.00-180.00  232
  5  ω     97.00 158.00   0.50    0.50    --   95.70  45.00  90.00  122
  6  ω    121.00 148.00   0.50    0.50    --   95.70 -15.00-150.00   54
  7  ω     10.00  54.00   0.50    0.50    --   95.70 -15.00-150.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0598359000
_diffrn_orient_matrix_UB_12      0.0364903000
_diffrn_orient_matrix_UB_13      0.0568093000
_diffrn_orient_matrix_UB_21      0.0028289000
_diffrn_orient_matrix_UB_22      -0.0959626000
_diffrn_orient_matrix_UB_23      0.1218891000
_diffrn_orient_matrix_UB_31      0.0278136000
_diffrn_orient_matrix_UB_32      0.0880899000
_diffrn_orient_matrix_UB_33      0.1099301000
_diffrn_oxdiff_digest_frames     
;
01d32a5dd388e677ea61447c065a22b6b900031b875
;
_diffrn_oxdiff_digest_hkl        
;
01c708d939fdeb61f36c8bd3f83f73002f2139
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2056
_reflns_number_total             2271
_reflns_odcompleteness_completeness 100.00
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_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    ?
_refine_diff_density_max         2.468
_refine_diff_density_min         -1.538
_refine_diff_density_rms         0.266
_refine_ls_extinction_coef       0.00063(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         2271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0610
_refine_ls_restrained_S_all      1.066
_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)+(0.1345P)²+3.2184P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1785
_refine_ls_wR_factor_ref         0.1826
_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) groups
2. Others
 Sof(C1GA)=Sof(H1GC)=Sof(H1GD)=0.5*(1-FVAR(2))
 Sof(C1GB)=Sof(H1GA)=Sof(H1GB)=0.5*FVAR(2)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7A,H7B), C1GB(H1GA,H1GB), C1GA(H1GC,H1GD)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C6(H6), C4(H4)
;
_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
Br3 Br 0.40864(2) 0.36884(5) -0.13812(7) 0.0298(3) Uani 1 1 d . . . . .
Br1 Br 0.44738(3) 0.82863(5) 0.39471(7) 0.0328(3) Uani 1 1 d . . . . .
Br2 Br 0.23892(3) 0.42394(7) 0.46028(9) 0.0471(3) Uani 1 1 d . . . . .
Cl1G Cl 0.31170(11) 0.7605(4) 0.6963(6) 0.1249(16) Uani 1 1 d . . . . .
N1 N 0.4091(2) 0.4560(5) 0.2042(6) 0.0318(11) Uani 1 1 d . . . . .
H1 H 0.412349 0.431286 0.113060 0.038 Uiso 1 1 calc R . . . .
C2 C 0.4412(2) 0.5813(5) 0.3979(6) 0.0255(12) Uani 1 1 d . . . . .
C3 C 0.4459(2) 0.5370(5) 0.2527(7) 0.0287(12) Uani 1 1 d . . . . .
H3 H 0.474796 0.563876 0.189203 0.034 Uiso 1 1 calc R . . . .
C6 C 0.3985(2) 0.5350(5) 0.4892(6) 0.0261(11) Uani 1 1 d . . . . .
H6 H 0.394646 0.562319 0.587407 0.031 Uiso 1 1 calc R . . . .
C5 C 0.3612(2) 0.4485(5) 0.4369(6) 0.0264(11) Uani 1 1 d . . . . .
C4 C 0.3679(3) 0.4117(5) 0.2888(7) 0.0297(12) Uani 1 1 d . . . . .
H4 H 0.343190 0.355609 0.248963 0.036 Uiso 1 1 calc R . . . .
C1 C 0.4799(3) 0.6750(5) 0.4509(7) 0.0317(13) Uani 1 1 d . . . . .
H1A H 0.517485 0.665630 0.405316 0.038 Uiso 1 1 calc R . . . .
H1B H 0.484269 0.670318 0.559429 0.038 Uiso 1 1 calc R . . . .
C7 C 0.3160(3) 0.3931(6) 0.5347(8) 0.0419(16) Uani 1 1 d . . . . .
H7A H 0.319464 0.423352 0.636488 0.050 Uiso 1 1 calc R . . . .
H7B H 0.322242 0.308904 0.538430 0.050 Uiso 1 1 calc R . . . .
C1GB C 0.250000 0.750000 0.772(4) 0.14(3) Uani 0.45(3) 2 d S T P A 1
H1GA H 0.252740 0.682333 0.837647 0.172 Uiso 0.223(17) 1 calc R . . A 1
H1GB H 0.247260 0.817665 0.837651 0.172 Uiso 0.223(17) 1 calc R . . A 1
C1GA C 0.250000 0.750000 0.611(3) 0.068(8) Uani 0.55(3) 2 d S T P A 2
H1GC H 0.247249 0.817943 0.545546 0.082 Uiso 0.277(17) 1 calc R . . A 2
H1GD H 0.252751 0.682055 0.545549 0.082 Uiso 0.277(17) 1 calc R . . A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.971(6) . ?
Br2 C7 1.946(7) . ?
Cl1G C1GB 1.591(15) . ?
Cl1G C1GA 1.630(11) . ?
N1 C3 1.331(8) . ?
N1 C4 1.319(8) . ?
C2 C3 1.388(8) . ?
C2 C6 1.388(8) . ?
C2 C1 1.475(8) . ?
C6 C5 1.393(8) . ?
C5 C4 1.388(8) . ?
C5 C7 1.505(8) . ?

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
C4 N1 C3 123.4(5) . . ?
C3 C2 C1 120.7(5) . . ?
C6 C2 C3 117.4(5) . . ?
C6 C2 C1 121.9(5) . . ?
N1 C3 C2 120.1(5) . . ?
C2 C6 C5 121.5(5) . . ?
C6 C5 C7 122.8(5) . . ?
C4 C5 C6 117.3(5) . . ?
C4 C5 C7 119.9(5) . . ?
N1 C4 C5 120.3(5) . . ?
C2 C1 Br1 109.0(4) . . ?
C5 C7 Br2 112.0(4) . . ?
Cl1G C1GB Cl1G 130(2) 2_565 . ?
Cl1G C1GA Cl1G 124.7(15) 2_565 . ?

_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 4.233
_oxdiff_exptl_absorpt_empirical_full_min 0.294
####################################################################### 
# 
# 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_CD2Cl2_148K
_database_code_depnum_ccdc_archive 'CCDC 2124427'
loop_
_audit_author_name
_audit_author_address
'Shohei Tashiro'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C7 H8 Br2 N, C0.5 H Cl'
_chemical_formula_sum            'C7.50 H9 Br3 Cl N'
_chemical_formula_weight         388.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNBrCl
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   23.3143(5)
_cell_length_b                   11.3349(3)
_cell_length_c                   8.8651(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2342.74(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4575
_cell_measurement_temperature    148
_cell_measurement_theta_max      71.4510
_cell_measurement_theta_min      3.8200
_shelx_estimated_absorpt_T_max   0.531
_shelx_estimated_absorpt_T_min   0.080
_exptl_absorpt_coefficient_mu    14.511
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.12679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
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    2.202
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6408
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.645
_diffrn_reflns_theta_min         3.792
_diffrn_ambient_temperature      148
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -86.00 -30.00   0.50    0.50    --    0.00 -38.00-150.00  112
  2  ω     37.00  88.00   0.50    0.50    --    0.00  38.00-120.00  102
  3  ω     68.00 116.00   0.50    0.50    --   95.70  61.00 -30.00   96
  4  ω    114.00 157.00   0.50    0.50    --   95.70  77.00-150.00   86
  5  ω    119.00 146.00   0.50    0.50    --   95.70  45.00  90.00   54
  6  ω    120.00 150.00   0.50    0.50    --   95.70  61.00 -30.00   60
  7  ω      6.00 115.00   0.50    0.50    --   95.70 -45.00-180.00  218
  8  ω     24.00 131.00   0.50    0.50    --   95.70 -82.00  60.00  214
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0594176000
_diffrn_orient_matrix_UB_12      0.0362272000
_diffrn_orient_matrix_UB_13      0.0602321000
_diffrn_orient_matrix_UB_21      0.0041958000
_diffrn_orient_matrix_UB_22      -0.0957836000
_diffrn_orient_matrix_UB_23      0.1226911000
_diffrn_orient_matrix_UB_31      0.0285549000
_diffrn_orient_matrix_UB_32      0.0893107000
_diffrn_orient_matrix_UB_33      0.1074692000
_diffrn_oxdiff_digest_frames     
;
014f11c1e00b89ddf9dbccb0f8449de42c000310d72
;
_diffrn_oxdiff_digest_hkl        
;
01c52acd7f2340912249179233f252a2b6a230
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2070
_reflns_number_total             2257
_reflns_odcompleteness_completeness 99.92
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_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    ?
_refine_diff_density_max         2.398
_refine_diff_density_min         -1.554
_refine_diff_density_rms         0.264
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         2257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0552
_refine_ls_restrained_S_all      1.095
_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)+(0.1145P)²+2.4789P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1559
_refine_ls_wR_factor_ref         0.1598
_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) groups
2. Others
 Fixed Sof: H1GA(0.5) H1GB(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7A,H7B), C1G(H1GA,H1GB)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C6(H6), C4(H4)
;
_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
Br3 Br 0.40850(2) 0.63164(5) 0.63843(6) 0.0227(2) Uani 1 1 d . . . . .
Br1 Br 0.44818(2) 0.17006(5) 0.10541(6) 0.0247(2) Uani 1 1 d . . . . .
Br2 Br 0.23859(2) 0.57504(6) 0.03944(7) 0.0350(3) Uani 1 1 d . . . . .
Cl1G Cl 0.31239(7) 0.2475(2) 0.2794(2) 0.0592(5) Uani 1 1 d . . . . .
N1 N 0.40938(18) 0.5438(4) 0.2962(5) 0.0237(9) Uani 1 1 d . . . . .
H1 H 0.412855 0.569449 0.389425 0.028 Uiso 1 1 calc R . . . .
C2 C 0.4414(2) 0.4182(4) 0.1010(6) 0.0188(10) Uani 1 1 d . . . . .
C3 C 0.4463(2) 0.4614(5) 0.2462(6) 0.0250(11) Uani 1 1 d . . . . .
H3 H 0.475823 0.432989 0.310633 0.030 Uiso 1 1 calc R . . . .
C6 C 0.3983(2) 0.4647(4) 0.0090(6) 0.0199(10) Uani 1 1 d . . . . .
H6 H 0.394600 0.437465 -0.091866 0.024 Uiso 1 1 calc R . . . .
C5 C 0.3608(2) 0.5505(4) 0.0630(6) 0.0206(10) Uani 1 1 d . . . . .
C1 C 0.4810(2) 0.3244(4) 0.0482(7) 0.0247(11) Uani 1 1 d . . . . .
H1A H 0.519163 0.334509 0.095378 0.030 Uiso 1 1 calc R . . . .
H1B H 0.485579 0.328918 -0.062618 0.030 Uiso 1 1 calc R . . . .
C4 C 0.3677(2) 0.5882(4) 0.2103(6) 0.0251(11) Uani 1 1 d . . . . .
H4 H 0.342589 0.646161 0.250523 0.030 Uiso 1 1 calc R . . . .
C7 C 0.3159(2) 0.6059(5) -0.0363(7) 0.0304(12) Uani 1 1 d . . . . .
H7A H 0.319460 0.574021 -0.139796 0.036 Uiso 1 1 calc R . . . .
H7B H 0.322308 0.692149 -0.040960 0.036 Uiso 1 1 calc R . . . .
C1G C 0.250000 0.250000 0.3917(11) 0.048(2) Uani 1 2 d S T P . .
H1GA H 0.250664 0.320648 0.457331 0.058 Uiso 0.5 1 calc R . . . .
H1GB H 0.249337 0.179352 0.457331 0.058 Uiso 0.5 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
Br1 C1 1.975(5) . ?
Br2 C7 1.954(6) . ?
Cl1G C1G 1.763(6) . ?
N1 C3 1.346(7) . ?
N1 C4 1.333(7) . ?
C2 C3 1.382(8) . ?
C2 C6 1.397(7) . ?
C2 C1 1.484(7) . ?
C6 C5 1.393(7) . ?
C5 C4 1.383(8) . ?
C5 C7 1.505(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
C4 N1 C3 122.7(5) . . ?
C3 C2 C6 118.1(5) . . ?
C3 C2 C1 119.7(5) . . ?
C6 C2 C1 122.2(5) . . ?
N1 C3 C2 119.9(5) . . ?
C5 C6 C2 120.9(5) . . ?
C6 C5 C7 121.8(5) . . ?
C4 C5 C6 117.8(5) . . ?
C4 C5 C7 120.3(5) . . ?
C2 C1 Br1 108.2(3) . . ?
N1 C4 C5 120.5(5) . . ?
C5 C7 Br2 111.5(4) . . ?
Cl1G C1G Cl1G 111.3(6) . 2 ?

_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 4.107
_oxdiff_exptl_absorpt_empirical_full_min 0.337
####################################################################### 
# 
# 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_DCM_168K
_database_code_depnum_ccdc_archive 'CCDC 2124419'
loop_
_audit_author_name
_audit_author_address
'Shohei Tashiro'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C7 H8 Br2 N, C0.5 H Cl'
_chemical_formula_sum            'C7.50 H9 Br3 Cl N'
_chemical_formula_weight         388.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNBrCl
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   23.3008(2)
_cell_length_b                   11.37200(10)
_cell_length_c                   8.87240(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2350.98(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4714
_cell_measurement_temperature    168
_cell_measurement_theta_max      71.3740
_cell_measurement_theta_min      3.8110
_shelx_estimated_absorpt_T_max   0.671
_shelx_estimated_absorpt_T_min   0.160
_exptl_absorpt_coefficient_mu    14.460
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40150
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    2.194
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6477
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.220
_diffrn_reflns_theta_min         3.794
_diffrn_ambient_temperature      168
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  52.00   0.50    0.50    --    0.00  38.00   0.00  154
  2  ω    -37.00  -1.00   0.50    0.50    --    0.00 -38.00 120.00   72
  3  ω     67.00  92.00   0.50    0.50    --   95.70  61.00 -60.00   50
  4  ω     34.00 116.00   0.50    0.50    --   95.70 -82.00-180.00  164
  5  ω     24.00  90.00   0.50    0.50    --   95.70 -45.00-180.00  132
  6  ω     74.00 129.00   0.50    0.50    --   95.70 -77.00-120.00  110
  7  ω     41.00 160.00   0.50    0.50    --   95.70  15.00-180.00  238
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0650778000
_diffrn_orient_matrix_UB_12      0.0218376000
_diffrn_orient_matrix_UB_13      -0.0118875000
_diffrn_orient_matrix_UB_21      -0.0102453000
_diffrn_orient_matrix_UB_22      -0.1332343000
_diffrn_orient_matrix_UB_23      -0.0157644000
_diffrn_orient_matrix_UB_31      -0.0054573000
_diffrn_orient_matrix_UB_32      -0.0107312000
_diffrn_orient_matrix_UB_33      0.1725785000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2098
_reflns_number_total             2268
_reflns_odcompleteness_completeness 99.88
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    ?
_refine_diff_density_max         1.376
_refine_diff_density_min         -1.308
_refine_diff_density_rms         0.137
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.078
_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)+(0.0527P)²+7.4516P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.0991
_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) groups
2. Others
 Sof(C1GB)=Sof(H1GC)=Sof(H1GD)=0.5*(1-FVAR(2))
 Sof(C1GA)=Sof(H1GB)=Sof(H1GA)=0.5*FVAR(2)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7A,H7B), C1GA(H1GB,H1GA), C1GB(H1GC,H1GD)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C6(H6), C4(H4)
;
_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
Br3 Br 0.59148(2) 0.36865(4) 0.63801(5) 0.02704(15) Uani 1 1 d . . . . .
Br1 Br 0.55246(2) 0.82929(4) 0.10512(5) 0.02973(16) Uani 1 1 d . . . . .
Br2 Br 0.76132(2) 0.42404(5) 0.03972(6) 0.04361(18) Uani 1 1 d . . . . .
Cl1G Cl 0.68827(8) 0.7430(3) 0.2947(3) 0.1092(9) Uani 1 1 d . . . . .
N1 N 0.59074(15) 0.4559(3) 0.2963(4) 0.0277(8) Uani 1 1 d . . . . .
H1 H 0.587130 0.430116 0.389308 0.033 Uiso 1 1 calc R . . . .
C2 C 0.55894(17) 0.5809(4) 0.1014(5) 0.0236(8) Uani 1 1 d . . . . .
C3 C 0.55385(17) 0.5377(4) 0.2465(5) 0.0250(8) Uani 1 1 d . . . . .
H3 H 0.524287 0.565932 0.310775 0.030 Uiso 1 1 calc R . . . .
C6 C 0.60228(17) 0.5356(4) 0.0100(4) 0.0235(8) Uani 1 1 d . . . . .
H6 H 0.606591 0.564128 -0.089944 0.028 Uiso 1 1 calc R . . . .
C5 C 0.63922(17) 0.4493(4) 0.0631(4) 0.0247(8) Uani 1 1 d . . . . .
C1 C 0.51974(19) 0.6763(4) 0.0498(5) 0.0278(9) Uani 1 1 d . . . . .
H1A H 0.481607 0.666704 0.097412 0.033 Uiso 1 1 calc R . . . .
H1B H 0.514790 0.671786 -0.060912 0.033 Uiso 1 1 calc R . . . .
C4 C 0.63257(19) 0.4122(4) 0.2110(5) 0.0276(9) Uani 1 1 d . . . . .
H4 H 0.658046 0.355226 0.251633 0.033 Uiso 1 1 calc R . . . .
C7 C 0.6841(2) 0.3946(5) -0.0352(6) 0.0389(11) Uani 1 1 d . . . . .
H7A H 0.680563 0.426577 -0.138503 0.047 Uiso 1 1 calc R . . . .
H7B H 0.677488 0.308643 -0.040312 0.047 Uiso 1 1 calc R . . . .
C1GA C 0.750000 0.750000 0.3896(17) 0.068(5) Uani 0.70(3) 2 d S T P A 1
H1GB H 0.748118 0.819863 0.455953 0.081 Uiso 0.352(13) 1 calc R . . A 1
H1GA H 0.751883 0.680136 0.455952 0.081 Uiso 0.352(13) 1 calc R . . A 1
C1GB C 0.750000 0.750000 0.232(4) 0.078(13) Uani 0.30(3) 2 d S T P A 2
H1GC H 0.751858 0.681055 0.164267 0.093 Uiso 0.148(13) 1 calc R . . A 2
H1GD H 0.748142 0.818944 0.164265 0.093 Uiso 0.148(13) 1 calc R . . A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.962(4) . ?
Br2 C7 1.948(5) . ?
Cl1G C1GA 1.669(8) . ?
Cl1G C1GB 1.543(12) . ?
N1 H1 0.8800 . ?
N1 C3 1.341(5) . ?
N1 C4 1.330(6) . ?
C2 C3 1.383(6) . ?
C2 C6 1.394(6) . ?
C2 C1 1.490(6) . ?
C3 H3 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.388(6) . ?
C5 C4 1.386(6) . ?
C5 C7 1.497(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C4 H4 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C1GA H1GB 0.9900 . ?
C1GA H1GA 0.9900 . ?
C1GB H1GC 0.9900 . ?
C1GB H1GD 0.9900 . ?

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
C3 N1 H1 118.6 . . ?
C4 N1 H1 118.6 . . ?
C4 N1 C3 122.8(4) . . ?
C3 C2 C6 118.2(4) . . ?
C3 C2 C1 119.5(4) . . ?
C6 C2 C1 122.3(4) . . ?
N1 C3 C2 119.9(4) . . ?
N1 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C2 C6 H6 119.5 . . ?
C5 C6 C2 120.9(4) . . ?
C5 C6 H6 119.5 . . ?
C6 C5 C7 122.0(4) . . ?
C4 C5 C6 117.8(4) . . ?
C4 C5 C7 120.2(4) . . ?
Br1 C1 H1A 109.8 . . ?
Br1 C1 H1B 109.8 . . ?
C2 C1 Br1 109.3(3) . . ?
C2 C1 H1A 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.3 . . ?
N1 C4 C5 120.4(4) . . ?
N1 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
Br2 C7 H7A 109.2 . . ?
Br2 C7 H7B 109.2 . . ?
C5 C7 Br2 112.0(3) . . ?
C5 C7 H7A 109.2 . . ?
C5 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
Cl1G C1GA Cl1G 119.4(9) 2_665 . ?
Cl1G C1GA H1GB 107.5 2_665 . ?
Cl1G C1GA H1GB 107.5 . . ?
Cl1G C1GA H1GA 107.5 2_665 . ?
Cl1G C1GA H1GA 107.5 . . ?
H1GB C1GA H1GA 107.0 . . ?
Cl1G C1GB Cl1G 138(2) 2_665 . ?
Cl1G C1GB H1GC 102.6 2_665 . ?
Cl1G C1GB H1GC 102.6 . . ?
Cl1G C1GB H1GD 102.6 2_665 . ?
Cl1G C1GB H1GD 102.6 . . ?
H1GC C1GB H1GD 105.0 . . ?

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
C2 C6 C5 C4 -1.8(6) . . . . ?
C2 C6 C5 C7 176.7(4) . . . . ?
C3 N1 C4 C5 -0.9(6) . . . . ?
C3 C2 C6 C5 0.1(6) . . . . ?
C3 C2 C1 Br1 86.7(4) . . . . ?
C6 C2 C3 N1 1.1(6) . . . . ?
C6 C2 C1 Br1 -91.1(4) . . . . ?
C6 C5 C4 N1 2.2(6) . . . . ?
C6 C5 C7 Br2 118.0(4) . . . . ?
C1 C2 C3 N1 -176.8(4) . . . . ?
C1 C2 C6 C5 178.0(4) . . . . ?
C4 N1 C3 C2 -0.8(6) . . . . ?
C4 C5 C7 Br2 -63.6(5) . . . . ?
C7 C5 C4 N1 -176.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.713
_oxdiff_exptl_absorpt_empirical_full_min 0.646
####################################################################### 
# 
# 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_DCM_193K
_database_code_depnum_ccdc_archive 'CCDC 2124412'
loop_
_audit_author_name
_audit_author_address
'Shohei Tashiro'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C7 H8 Br2 N, C0.5 H Cl'
_chemical_formula_sum            'C7.50 H9 Br3 Cl N'
_chemical_formula_weight         388.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNBrCl
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   23.2933(3)
_cell_length_b                   11.40910(10)
_cell_length_c                   8.88390(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2360.95(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4251
_cell_measurement_temperature    193
_cell_measurement_theta_max      71.7610
_cell_measurement_theta_min      4.2990
_shelx_estimated_absorpt_T_max   0.672
_shelx_estimated_absorpt_T_min   0.161
_exptl_absorpt_coefficient_mu    14.399
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    2.185
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6338
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.225
_diffrn_reflns_theta_min         3.795
_diffrn_ambient_temperature      193
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  52.00   0.50    0.50    --    0.00  38.00   0.00  158
  2  ω    -37.00  -1.00   0.50    0.50    --    0.00 -38.00 120.00   72
  3  ω     67.00  93.00   0.50    0.50    --   95.70  61.00 -60.00   52
  4  ω     52.00 116.00   0.50    0.50    --   95.70 -82.00-180.00  128
  5  ω     13.00  90.00   0.50    0.50    --   95.70 -45.00-180.00  154
  6  ω     74.00 130.00   0.50    0.50    --   95.70 -77.00-120.00  112
  7  ω     41.00 155.00   0.50    0.50    --   95.70  15.00-180.00  228
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0650753000
_diffrn_orient_matrix_UB_12      -0.0220168000
_diffrn_orient_matrix_UB_13      -0.0119435000
_diffrn_orient_matrix_UB_21      0.0103385000
_diffrn_orient_matrix_UB_22      0.1327495000
_diffrn_orient_matrix_UB_23      -0.0158950000
_diffrn_orient_matrix_UB_31      0.0054989000
_diffrn_orient_matrix_UB_32      0.0107728000
_diffrn_orient_matrix_UB_33      0.1723579000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2087
_reflns_number_total             2274
_reflns_odcompleteness_completeness 99.84
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    ?
_refine_diff_density_max         1.199
_refine_diff_density_min         -1.232
_refine_diff_density_rms         0.141
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.064
_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)+(0.0589P)²+7.4629P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1058
_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) groups
2. Others
 Sof(C1GA)=Sof(H1GC)=Sof(H1GD)=0.5*(1-FVAR(2))
 Sof(C1GB)=Sof(H1GA)=Sof(H1GB)=0.5*FVAR(2)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7A,H7B), C1GB(H1GA,H1GB), C1GA(H1GC,H1GD)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C6(H6), C4(H4)
;
_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
Br3 Br 0.40863(2) 0.63106(4) 1.13744(5) 0.03099(16) Uani 1 1 d . . . . .
Br1 Br 0.44700(2) 0.17142(4) 0.60541(5) 0.03400(17) Uani 1 1 d . . . . .
Br2 Br 0.23886(2) 0.57651(6) 0.53925(7) 0.0508(2) Uani 1 1 d . . . . .
Cl1G Cl 0.31139(10) 0.2292(3) 0.3213(4) 0.1264(12) Uani 1 1 d . . . . .
N1 N 0.40935(16) 0.5442(3) 0.7960(4) 0.0304(8) Uani 1 1 d . . . . .
H1 H 0.412780 0.569436 0.889208 0.037 Uiso 1 1 calc R . . . .
C3 C 0.44632(18) 0.4630(4) 0.7466(5) 0.0286(9) Uani 1 1 d . . . . .
H3 H 0.476093 0.435489 0.810602 0.034 Uiso 1 1 calc R . . . .
C2 C 0.44099(18) 0.4194(4) 0.6021(5) 0.0261(9) Uani 1 1 d . . . . .
C6 C 0.39757(18) 0.4647(4) 0.5109(5) 0.0272(8) Uani 1 1 d . . . . .
H6 H 0.393160 0.436067 0.411110 0.033 Uiso 1 1 calc R . . . .
C4 C 0.36764(19) 0.5885(4) 0.7108(5) 0.0305(9) Uani 1 1 d . . . . .
H4 H 0.342498 0.646027 0.751113 0.037 Uiso 1 1 calc R . . . .
C5 C 0.36076(19) 0.5509(4) 0.5637(5) 0.0288(9) Uani 1 1 d . . . . .
C1 C 0.4800(2) 0.3234(4) 0.5503(5) 0.0310(9) Uani 1 1 d . . . . .
H1A H 0.518191 0.332464 0.597789 0.037 Uiso 1 1 calc R . . . .
H1B H 0.484939 0.327816 0.439760 0.037 Uiso 1 1 calc R . . . .
C7 C 0.3162(2) 0.6062(5) 0.4659(6) 0.0438(12) Uani 1 1 d . . . . .
H7A H 0.319891 0.575071 0.362334 0.053 Uiso 1 1 calc R . . . .
H7B H 0.322866 0.691860 0.461905 0.053 Uiso 1 1 calc R . . . .
C1GB C 0.250000 0.250000 0.229(2) 0.109(9) Uani 0.65(3) 2 d S T P A 1
H1GA H 0.255582 0.318709 0.162789 0.131 Uiso 0.325(15) 1 calc R . . A 1
H1GB H 0.244417 0.181290 0.162791 0.131 Uiso 0.325(15) 1 calc R . . A 1
C1GA C 0.250000 0.250000 0.389(5) 0.096(14) Uani 0.35(3) 2 d S T P A 2
H1GC H 0.244472 0.181970 0.456713 0.115 Uiso 0.175(15) 1 calc R . . A 2
H1GD H 0.255527 0.318028 0.456715 0.115 Uiso 0.175(15) 1 calc R . . A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.959(4) . ?
Br2 C7 1.946(5) . ?
Cl1G C1GB 1.664(9) . ?
Cl1G C1GA 1.569(16) . ?
N1 H1 0.8800 . ?
N1 C3 1.339(6) . ?
N1 C4 1.331(6) . ?
C3 H3 0.9500 . ?
C3 C2 1.383(6) . ?
C2 C6 1.395(6) . ?
C2 C1 1.495(6) . ?
C6 H6 0.9500 . ?
C6 C5 1.387(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(6) . ?
C5 C7 1.493(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C1GB H1GA 0.9900 . ?
C1GB H1GB 0.9900 . ?
C1GA H1GC 0.9900 . ?
C1GA H1GD 0.9900 . ?

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
C3 N1 H1 118.5 . . ?
C4 N1 H1 118.5 . . ?
C4 N1 C3 123.1(4) . . ?
N1 C3 H3 120.1 . . ?
N1 C3 C2 119.7(4) . . ?
C2 C3 H3 120.1 . . ?
C3 C2 C6 118.1(4) . . ?
C3 C2 C1 119.7(4) . . ?
C6 C2 C1 122.2(4) . . ?
C2 C6 H6 119.5 . . ?
C5 C6 C2 121.0(4) . . ?
C5 C6 H6 119.5 . . ?
N1 C4 H4 119.9 . . ?
N1 C4 C5 120.3(4) . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C7 122.2(4) . . ?
C4 C5 C6 117.8(4) . . ?
C4 C5 C7 119.9(4) . . ?
Br1 C1 H1A 109.8 . . ?
Br1 C1 H1B 109.8 . . ?
C2 C1 Br1 109.4(3) . . ?
C2 C1 H1A 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
Br2 C7 H7A 109.2 . . ?
Br2 C7 H7B 109.2 . . ?
C5 C7 Br2 112.0(3) . . ?
C5 C7 H7A 109.2 . . ?
C5 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
Cl1G C1GB Cl1G 121.1(11) 2 . ?
Cl1G C1GB H1GA 107.0 . . ?
Cl1G C1GB H1GA 107.0 2 . ?
Cl1G C1GB H1GB 107.0 . . ?
Cl1G C1GB H1GB 107.0 2 . ?
H1GA C1GB H1GB 106.8 . . ?
Cl1G C1GA Cl1G 135(3) 2 . ?
Cl1G C1GA H1GC 103.5 . . ?
Cl1G C1GA H1GC 103.5 2 . ?
Cl1G C1GA H1GD 103.5 . . ?
Cl1G C1GA H1GD 103.5 2 . ?
H1GC C1GA H1GD 105.3 . . ?

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 C3 C2 C6 1.7(6) . . . . ?
N1 C3 C2 C1 -176.2(4) . . . . ?
N1 C4 C5 C6 1.5(6) . . . . ?
N1 C4 C5 C7 -176.3(4) . . . . ?
C3 N1 C4 C5 0.1(7) . . . . ?
C3 C2 C6 C5 -0.1(6) . . . . ?
C3 C2 C1 Br1 87.0(4) . . . . ?
C2 C6 C5 C4 -1.5(6) . . . . ?
C2 C6 C5 C7 176.2(4) . . . . ?
C6 C2 C1 Br1 -90.8(4) . . . . ?
C6 C5 C7 Br2 117.5(4) . . . . ?
C4 N1 C3 C2 -1.7(6) . . . . ?
C4 C5 C7 Br2 -64.8(5) . . . . ?
C1 C2 C6 C5 177.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.705
_oxdiff_exptl_absorpt_empirical_full_min 0.667
####################################################################### 
# 
# 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_CD2Cl2_223K
_database_code_depnum_ccdc_archive 'CCDC 2124424'
loop_
_audit_author_name
_audit_author_address
'Shohei Tashiro'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C7 H8 Br2 N, C0.5 H Cl'
_chemical_formula_sum            'C7.50 H9 Br3 Cl N'
_chemical_formula_weight         388.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNBrCl
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   23.3005(4)
_cell_length_b                   11.4213(2)
_cell_length_c                   8.8820(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2363.70(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4412
_cell_measurement_temperature    223
_cell_measurement_theta_max      72.0130
_cell_measurement_theta_min      3.8010
_shelx_estimated_absorpt_T_max   0.533
_shelx_estimated_absorpt_T_min   0.081
_exptl_absorpt_coefficient_mu    14.382
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
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    2.183
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6836
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.214
_diffrn_reflns_theta_min         3.794
_diffrn_ambient_temperature      223
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     48.00  79.00   0.50    0.50    --    0.00  38.00 150.00   62
  2  ω    -27.00  32.00   0.50    0.50    --    0.00  38.00 -60.00  118
  3  ω      6.00 120.00   0.50    0.50    --   95.70 -45.00-180.00  228
  4  ω     75.00 110.00   0.50    0.50    --   95.70 -45.00  30.00   70
  5  ω    153.00 179.00   0.50    0.50    --   95.70  30.00 -60.00   52
  6  ω     65.00 121.00   0.50    0.50    --   95.70  30.00 -60.00  112
  7  ω      7.00  60.00   0.50    0.50    --   95.70 -45.00  30.00  106
  8  ω     31.00 126.00   0.50    0.50    --   95.70 -30.00  30.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0599705000
_diffrn_orient_matrix_UB_12      0.0364591000
_diffrn_orient_matrix_UB_13      0.0561163000
_diffrn_orient_matrix_UB_21      0.0026057000
_diffrn_orient_matrix_UB_22      -0.0957541000
_diffrn_orient_matrix_UB_23      0.1217604000
_diffrn_orient_matrix_UB_31      0.0277453000
_diffrn_orient_matrix_UB_32      0.0877224000
_diffrn_orient_matrix_UB_33      0.1099995000
_diffrn_oxdiff_digest_frames     
;
011e305813a0b529be0d9ed83ffa80147900030fc7e
;
_diffrn_oxdiff_digest_hkl        
;
0135b827fc95daa0d57411ffe8fb9cfcaa823c
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2047
_reflns_number_total             2284
_reflns_odcompleteness_completeness 99.96
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_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    ?
_refine_diff_density_max         3.622
_refine_diff_density_min         -1.480
_refine_diff_density_rms         0.309
_refine_ls_extinction_coef       0.0011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         2284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0811
_refine_ls_restrained_S_all      1.060
_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)+(0.1745P)²+5.8075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2268
_refine_ls_wR_factor_ref         0.2321
_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) groups
2. Others
 Fixed Sof: H1GA(0.5) H1GB(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7A,H7B), C1G(H1GA,H1GB)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C6(H6), C4(H4)
;
_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
Br3 Br 0.59126(3) 0.63095(6) -0.13750(8) 0.0341(4) Uani 1 1 d . . . . .
Br1 Br 0.55335(4) 0.17205(6) 0.39442(9) 0.0376(4) Uani 1 1 d . . . . .
Br2 Br 0.76108(4) 0.57669(9) 0.46086(11) 0.0544(4) Uani 1 1 d . . . . .
Cl1G Cl 0.68834(17) 0.2243(4) 0.6646(7) 0.1139(14) Uani 1 1 d . . . . .
N1 N 0.5905(3) 0.5443(6) 0.2035(7) 0.0369(14) Uani 1 1 d . . . . .
H1 H 0.587221 0.568627 0.112321 0.044 Uiso 1 1 calc R . . . .
C2 C 0.5593(3) 0.4194(6) 0.3973(8) 0.0291(14) Uani 1 1 d . . . . .
C3 C 0.5538(3) 0.4638(6) 0.2537(8) 0.0335(15) Uani 1 1 d . . . . .
H3 H 0.524306 0.437448 0.191623 0.040 Uiso 1 1 calc R . . . .
C6 C 0.6019(3) 0.4653(6) 0.4884(8) 0.0314(14) Uani 1 1 d . . . . .
H6 H 0.605885 0.437609 0.586291 0.038 Uiso 1 1 calc R . . . .
C1 C 0.5197(3) 0.3245(6) 0.4495(9) 0.0344(15) Uani 1 1 d . . . . .
H1A H 0.482433 0.333400 0.402312 0.041 Uiso 1 1 calc R . . . .
H1B H 0.514724 0.329084 0.557748 0.041 Uiso 1 1 calc R . . . .
C5 C 0.6392(3) 0.5525(6) 0.4367(8) 0.0319(14) Uani 1 1 d . . . . .
C4 C 0.6319(3) 0.5883(6) 0.2895(8) 0.0334(15) Uani 1 1 d . . . . .
H4 H 0.656512 0.644365 0.249566 0.040 Uiso 1 1 calc R . . . .
C7 C 0.6839(3) 0.6067(8) 0.5346(10) 0.046(2) Uani 1 1 d . . . . .
H7A H 0.680297 0.575802 0.635835 0.055 Uiso 1 1 calc R . . . .
H7B H 0.677613 0.690590 0.539165 0.055 Uiso 1 1 calc R . . . .
C1G C 0.750000 0.250000 0.769(3) 0.168(16) Uani 1 2 d S T P . .
H1GA H 0.756723 0.182918 0.833290 0.202 Uiso 0.5 1 calc R . . . .
H1GB H 0.743277 0.317083 0.833288 0.202 Uiso 0.5 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
Br1 C1 1.971(7) . ?
Br2 C7 1.944(8) . ?
Cl1G C1G 1.734(15) . ?
N1 C3 1.332(10) . ?
N1 C4 1.330(10) . ?
C2 C3 1.379(10) . ?
C2 C6 1.385(10) . ?
C2 C1 1.497(10) . ?
C6 C5 1.399(10) . ?
C5 C4 1.380(11) . ?
C5 C7 1.491(10) . ?

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
C4 N1 C3 122.4(6) . . ?
C3 C2 C6 117.9(7) . . ?
C3 C2 C1 119.7(7) . . ?
C6 C2 C1 122.4(6) . . ?
N1 C3 C2 120.2(7) . . ?
C2 C6 C5 121.6(6) . . ?
C2 C1 Br1 108.5(5) . . ?
C6 C5 C7 122.5(7) . . ?
C4 C5 C6 116.4(6) . . ?
C4 C5 C7 121.0(7) . . ?
N1 C4 C5 121.4(6) . . ?
C5 C7 Br2 112.1(5) . . ?
Cl1G C1G Cl1G 115.5(16) . 2_655 ?

_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 3.433
_oxdiff_exptl_absorpt_empirical_full_min 0.196
####################################################################### 
# 
# 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_DCM_293K
_database_code_depnum_ccdc_archive 'CCDC 2124417'
loop_
_audit_author_name
_audit_author_address
'Shohei Tashiro'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C7 H8 Br2 N, C0.5 H Cl'
_chemical_formula_sum            'C7.50 H9 Br3 Cl N'
_chemical_formula_weight         388.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNBrCl
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   23.3401(4)
_cell_length_b                   11.5126(2)
_cell_length_c                   8.92070(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2397.04(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4106
_cell_measurement_temperature    293
_cell_measurement_theta_max      71.7880
_cell_measurement_theta_min      4.2660
_shelx_estimated_absorpt_T_max   0.765
_shelx_estimated_absorpt_T_min   0.437
_exptl_absorpt_coefficient_mu    14.182
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    2.152
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7426
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.006
_diffrn_reflns_theta_min         3.788
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  20.00   0.50    0.76    --    0.00  38.00   0.00   64
  2  ω    -48.00  19.00   0.50    0.76    --    0.00 -19.00 120.00  134
  3  ω     98.00 185.00   0.50    3.05    --   95.70  45.00 -30.00  174
  4  ω     30.00 124.00   0.50    3.05    --   95.70 -61.00 -60.00  188
  5  ω     69.00 160.00   0.50    3.05    --   95.70  45.00 -90.00  182
  6  ω    141.00 176.00   0.50    3.05    --   95.70  45.00-180.00   70
  7  ω     80.00 159.00   0.50    3.05    --   95.70  61.00-150.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0383150000
_diffrn_orient_matrix_UB_12      -0.0802891000
_diffrn_orient_matrix_UB_13      -0.0950459000
_diffrn_orient_matrix_UB_21      -0.0536472000
_diffrn_orient_matrix_UB_22      -0.0627314000
_diffrn_orient_matrix_UB_23      -0.0597674000
_diffrn_orient_matrix_UB_31      -0.0032236000
_diffrn_orient_matrix_UB_32      0.0868520000
_diffrn_orient_matrix_UB_33      -0.1311041000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2054
_reflns_number_total             2302
_reflns_odcompleteness_completeness 99.88
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    ?
_refine_diff_density_max         1.198
_refine_diff_density_min         -1.255
_refine_diff_density_rms         0.111
_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     114
_refine_ls_number_reflns         2302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0393
_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)+(0.0519P)²+6.5271P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1085
_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) groups
2. Others
 Fixed Sof: H1GA(0.5) H1GB(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C1(H1A,H1B), C1G(H1GA,H1GB)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C6(H6), C3(H3)
;
_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
Br3 Br 0.40887(2) 0.36971(5) 0.63627(5) 0.04788(18) Uani 1 1 d . . . . .
Br2 Br 0.44618(2) 0.82591(5) 0.10726(6) 0.05254(18) Uani 1 1 d . . . . .
Br1 Br 0.23999(3) 0.42306(7) 0.03786(8) 0.0767(2) Uani 1 1 d . . . . .
N1 N 0.40946(18) 0.4553(4) 0.2966(4) 0.0470(9) Uani 1 1 d . . . . .
H1 H 0.412821 0.430712 0.387190 0.056 Uiso 1 1 calc R . . . .
C5 C 0.44063(19) 0.5800(4) 0.1045(5) 0.0377(9) Uani 1 1 d . . . . .
C4 C 0.4459(2) 0.5367(4) 0.2479(5) 0.0427(10) Uani 1 1 d . . . . .
H4 H 0.474664 0.564036 0.310662 0.051 Uiso 1 1 calc R . . . .
C6 C 0.39749(19) 0.5345(4) 0.0133(5) 0.0404(10) Uani 1 1 d . . . . .
H6 H 0.393029 0.562596 -0.083739 0.048 Uiso 1 1 calc R . . . .
C2 C 0.3615(2) 0.4490(4) 0.0649(5) 0.0433(10) Uani 1 1 d . . . . .
C3 C 0.3687(2) 0.4113(4) 0.2118(6) 0.0454(11) Uani 1 1 d . . . . .
H3 H 0.344468 0.354585 0.250490 0.054 Uiso 1 1 calc R . . . .
C7 C 0.4793(2) 0.6753(4) 0.0532(6) 0.0451(10) Uani 1 1 d . . . . .
H7A H 0.484332 0.670934 -0.054619 0.054 Uiso 1 1 calc R . . . .
H7B H 0.516654 0.666886 0.099848 0.054 Uiso 1 1 calc R . . . .
C1 C 0.3170(2) 0.3932(6) -0.0318(7) 0.0646(16) Uani 1 1 d . . . . .
H1A H 0.323420 0.310027 -0.033938 0.077 Uiso 1 1 calc R . . . .
H1B H 0.320838 0.422158 -0.133423 0.077 Uiso 1 1 calc R . . . .
Cl1G Cl 0.31104(12) 0.7781(3) -0.1630(5) 0.1484(11) Uani 1 1 d . . . . .
C1G C 0.250000 0.750000 -0.2673(18) 0.251(16) Uani 1 2 d S T P . .
H1GA H 0.257418 0.683727 -0.331590 0.301 Uiso 0.5 1 calc R . . . .
H1GB H 0.242582 0.816271 -0.331595 0.301 Uiso 0.5 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
Br2 C7 1.959(5) . ?
Br1 C1 1.932(6) . ?
N1 H1 0.8600 . ?
N1 C4 1.337(6) . ?
N1 C3 1.318(7) . ?
C5 C4 1.378(6) . ?
C5 C6 1.396(6) . ?
C5 C7 1.494(6) . ?
C4 H4 0.9300 . ?
C6 H6 0.9300 . ?
C6 C2 1.373(7) . ?
C2 C3 1.390(7) . ?
C2 C1 1.496(7) . ?
C3 H3 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
Cl1G C1G 1.732(9) . ?
C1G H1GA 0.9700 . ?
C1G H1GB 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
C4 N1 H1 118.6 . . ?
C3 N1 H1 118.6 . . ?
C3 N1 C4 122.8(4) . . ?
C4 C5 C6 118.0(4) . . ?
C4 C5 C7 119.8(4) . . ?
C6 C5 C7 122.2(4) . . ?
N1 C4 C5 119.9(4) . . ?
N1 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C5 C6 H6 119.5 . . ?
C2 C6 C5 121.0(4) . . ?
C2 C6 H6 119.5 . . ?
C6 C2 C3 117.8(4) . . ?
C6 C2 C1 122.7(5) . . ?
C3 C2 C1 119.6(5) . . ?
N1 C3 C2 120.5(4) . . ?
N1 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
Br2 C7 H7A 109.7 . . ?
Br2 C7 H7B 109.7 . . ?
C5 C7 Br2 109.6(3) . . ?
C5 C7 H7A 109.7 . . ?
C5 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
Br1 C1 H1A 109.1 . . ?
Br1 C1 H1B 109.1 . . ?
C2 C1 Br1 112.7(4) . . ?
C2 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
Cl1G C1G Cl1G 115.0(9) . 2_565 ?
Cl1G C1G H1GA 108.5 2_565 . ?
Cl1G C1G H1GA 108.5 . . ?
Cl1G C1G H1GB 108.5 2_565 . ?
Cl1G C1G H1GB 108.5 . . ?
H1GA C1G H1GB 107.5 . . ?

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
C5 C6 C2 C3 1.5(7) . . . . ?
C5 C6 C2 C1 -176.5(5) . . . . ?
C4 N1 C3 C2 -0.3(7) . . . . ?
C4 C5 C6 C2 -0.3(7) . . . . ?
C4 C5 C7 Br2 -87.2(5) . . . . ?
C6 C5 C4 N1 -1.3(7) . . . . ?
C6 C5 C7 Br2 90.8(5) . . . . ?
C6 C2 C3 N1 -1.3(7) . . . . ?
C6 C2 C1 Br1 -116.0(5) . . . . ?
C3 N1 C4 C5 1.6(7) . . . . ?
C3 C2 C1 Br1 66.0(6) . . . . ?
C7 C5 C4 N1 176.7(4) . . . . ?
C7 C5 C6 C2 -178.3(4) . . . . ?
C1 C2 C3 N1 176.8(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.598
_oxdiff_exptl_absorpt_empirical_full_min 0.549
####################################################################### 
# 
# 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_DCM_148K
_database_code_depnum_ccdc_archive 'CCDC 2124428'
loop_
_audit_author_name
_audit_author_address
'Shohei Tashiro'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C7 H8 Br2 N, C0.5 H Cl'
_chemical_formula_sum            'C7.50 H9 Br3 Cl N'
_chemical_formula_weight         388.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNBrCl
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   23.3045(2)
_cell_length_b                   11.34090(10)
_cell_length_c                   8.86430(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2342.78(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4612
_cell_measurement_temperature    148
_cell_measurement_theta_max      71.5300
_cell_measurement_theta_min      3.8120
_shelx_estimated_absorpt_T_max   0.670
_shelx_estimated_absorpt_T_min   0.159
_exptl_absorpt_coefficient_mu    14.510
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    2.202
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6417
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.281
_diffrn_reflns_theta_min         3.793
_diffrn_ambient_temperature      148
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  51.00   0.50    0.50    --    0.00  38.00   0.00  154
  2  ω    -35.00   1.00   0.50    0.50    --    0.00 -38.00 120.00   72
  3  ω     67.00  92.00   0.50    0.50    --   95.70  61.00 -60.00   50
  4  ω     40.00 116.00   0.50    0.50    --   95.70 -82.00-180.00  152
  5  ω     13.00  87.00   0.50    0.50    --   95.70 -45.00-180.00  148
  6  ω     74.00 129.00   0.50    0.50    --   95.70 -77.00-120.00  110
  7  ω     41.00 158.00   0.50    0.50    --   95.70  15.00-180.00  234
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0650975000
_diffrn_orient_matrix_UB_12      0.0214596000
_diffrn_orient_matrix_UB_13      -0.0122845000
_diffrn_orient_matrix_UB_21      -0.0100324000
_diffrn_orient_matrix_UB_22      -0.1336723000
_diffrn_orient_matrix_UB_23      -0.0158383000
_diffrn_orient_matrix_UB_31      -0.0055875000
_diffrn_orient_matrix_UB_32      -0.0107923000
_diffrn_orient_matrix_UB_33      0.1726790000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2100
_reflns_number_total             2259
_reflns_odcompleteness_completeness 99.92
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    ?
_refine_diff_density_max         1.296
_refine_diff_density_min         -0.789
_refine_diff_density_rms         0.151
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         2259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.053
_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)+(0.0639P)²+4.3087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.0993
_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) groups
2. Others
 Fixed Sof: H1GA(0.5) H1GB(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7A,H7B), C1G(H1GA,H1GB)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C6(H6), C4(H4)
;
_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
Br3 Br 0.40841(2) 0.63162(3) 0.63852(4) 0.02457(15) Uani 1 1 d . . . . .
Br1 Br 0.44805(2) 0.17007(3) 0.10515(5) 0.02681(15) Uani 1 1 d . . . . .
Br2 Br 0.23853(2) 0.57547(5) 0.03970(5) 0.03840(17) Uani 1 1 d . . . . .
Cl1G Cl 0.31237(6) 0.24913(17) 0.28119(19) 0.0693(4) Uani 1 1 d . . . . .
N1 N 0.40913(14) 0.5439(3) 0.2963(4) 0.0250(7) Uani 1 1 d . . . . .
H1 H 0.412473 0.569525 0.389568 0.030 Uiso 1 1 calc R . . . .
C2 C 0.44120(16) 0.4190(3) 0.1011(4) 0.0221(8) Uani 1 1 d . . . . .
C3 C 0.44640(16) 0.4622(3) 0.2468(4) 0.0238(8) Uani 1 1 d . . . . .
H3 H 0.476063 0.434323 0.311011 0.029 Uiso 1 1 calc R . . . .
C6 C 0.39784(15) 0.4648(3) 0.0094(4) 0.0220(7) Uani 1 1 d . . . . .
H6 H 0.393773 0.436692 -0.090962 0.026 Uiso 1 1 calc R . . . .
C5 C 0.36070(16) 0.5504(3) 0.0627(4) 0.0226(7) Uani 1 1 d . . . . .
C1 C 0.48070(17) 0.3237(3) 0.0496(5) 0.0255(8) Uani 1 1 d . . . . .
H1A H 0.518763 0.333555 0.097609 0.031 Uiso 1 1 calc R . . . .
H1B H 0.485749 0.328145 -0.061110 0.031 Uiso 1 1 calc R . . . .
C4 C 0.36746(17) 0.5878(3) 0.2108(4) 0.0256(8) Uani 1 1 d . . . . .
H4 H 0.342082 0.645206 0.251297 0.031 Uiso 1 1 calc R . . . .
C7 C 0.31570(18) 0.6053(4) -0.0365(5) 0.0354(10) Uani 1 1 d . . . . .
H7A H 0.319141 0.572916 -0.139804 0.042 Uiso 1 1 calc R . . . .
H7B H 0.322235 0.691493 -0.042050 0.042 Uiso 1 1 calc R . . . .
C1G C 0.250000 0.250000 0.3895(9) 0.056(2) Uani 1 2 d S T P . .
H1GA H 0.250232 0.320516 0.455371 0.068 Uiso 0.5 1 calc R . . . .
H1GB H 0.249768 0.179484 0.455370 0.068 Uiso 0.5 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
Br1 C1 1.964(4) . ?
Br2 C7 1.951(4) . ?
Cl1G C1G 1.742(5) . ?
N1 H1 0.8800 . ?
N1 C3 1.344(5) . ?
N1 C4 1.329(5) . ?
C2 C3 1.386(5) . ?
C2 C6 1.397(5) . ?
C2 C1 1.491(5) . ?
C3 H3 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.384(5) . ?
C5 C4 1.388(5) . ?
C5 C7 1.504(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C4 H4 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C1G H1GA 0.9900 . ?
C1G H1GB 0.9900 . ?

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
C3 N1 H1 118.5 . . ?
C4 N1 H1 118.5 . . ?
C4 N1 C3 123.0(3) . . ?
C3 C2 C6 118.3(4) . . ?
C3 C2 C1 119.2(4) . . ?
C6 C2 C1 122.5(3) . . ?
N1 C3 C2 119.4(3) . . ?
N1 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C2 C6 H6 119.5 . . ?
C5 C6 C2 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C6 C5 C4 117.8(3) . . ?
C6 C5 C7 121.8(3) . . ?
C4 C5 C7 120.4(3) . . ?
Br1 C1 H1A 109.9 . . ?
Br1 C1 H1B 109.9 . . ?
C2 C1 Br1 109.1(3) . . ?
C2 C1 H1A 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
N1 C4 C5 120.5(3) . . ?
N1 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
Br2 C7 H7A 109.3 . . ?
Br2 C7 H7B 109.3 . . ?
C5 C7 Br2 111.6(3) . . ?
C5 C7 H7A 109.3 . . ?
C5 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
Cl1G C1G Cl1G 113.1(5) . 2 ?
Cl1G C1G H1GA 109.0 . . ?
Cl1G C1G H1GA 109.0 2 . ?
Cl1G C1G H1GB 109.0 . . ?
Cl1G C1G H1GB 109.0 2 . ?
H1GA C1G H1GB 107.8 . . ?

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
C2 C6 C5 C4 -1.0(5) . . . . ?
C2 C6 C5 C7 176.8(4) . . . . ?
C3 N1 C4 C5 -0.3(6) . . . . ?
C3 C2 C6 C5 -0.5(5) . . . . ?
C3 C2 C1 Br1 86.8(4) . . . . ?
C6 C2 C3 N1 1.6(5) . . . . ?
C6 C2 C1 Br1 -91.4(4) . . . . ?
C6 C5 C4 N1 1.4(6) . . . . ?
C6 C5 C7 Br2 118.6(4) . . . . ?
C1 C2 C3 N1 -176.7(3) . . . . ?
C1 C2 C6 C5 177.8(3) . . . . ?
C4 N1 C3 C2 -1.2(6) . . . . ?
C4 C5 C7 Br2 -63.6(4) . . . . ?
C7 C5 C4 N1 -176.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.149
_oxdiff_exptl_absorpt_empirical_full_min 0.683
####################################################################### 
# 
# 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_CD2Cl2_193K
_database_code_depnum_ccdc_archive 'CCDC 2124425'
loop_
_audit_author_name
_audit_author_address
'Shohei Tashiro'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C7 H8 Br2 N, C0.5 H Cl'
_chemical_formula_sum            'C7.50 H9 Br3 Cl N'
_chemical_formula_weight         388.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNBrCl
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'

_cell_length_a                   23.3229(4)
_cell_length_b                   11.38030(19)
_cell_length_c                   8.87309(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2355.11(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4600
_cell_measurement_temperature    193
_cell_measurement_theta_max      72.0750
_cell_measurement_theta_min      3.7960
_shelx_estimated_absorpt_T_max   0.532
_shelx_estimated_absorpt_T_min   0.081
_exptl_absorpt_coefficient_mu    14.434
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.08118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
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    2.190
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6488
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.350
_diffrn_reflns_theta_min         3.791
_diffrn_ambient_temperature      193
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     39.00  88.00   0.50    0.50    --    0.00  38.00-120.00   98
  2  ω    -87.00 -31.00   0.50    0.50    --    0.00 -38.00-150.00  112
  3  ω      7.00 118.00   0.50    0.50    --   95.70 -45.00  30.00  222
  4  ω      6.00 118.00   0.50    0.50    --   95.70 -61.00-180.00  224
  5  ω     97.00 144.00   0.50    0.50    --   95.70  45.00  90.00   94
  6  ω    120.00 148.00   0.50    0.50    --   95.70 -15.00-150.00   56
  7  ω      8.00  65.00   0.50    0.50    --   95.70 -15.00-150.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0596662000
_diffrn_orient_matrix_UB_12      0.0367748000
_diffrn_orient_matrix_UB_13      0.0575493000
_diffrn_orient_matrix_UB_21      0.0030204000
_diffrn_orient_matrix_UB_22      -0.0958044000
_diffrn_orient_matrix_UB_23      0.1222121000
_diffrn_orient_matrix_UB_31      0.0280835000
_diffrn_orient_matrix_UB_32      0.0882922000
_diffrn_orient_matrix_UB_33      0.1092127000
_diffrn_oxdiff_digest_frames     
;
019eebbf6bc3b153c5b8d86c9d9ed72a0800031c5c1
;
_diffrn_oxdiff_digest_hkl        
;
01cb5170a536b92c6ed2c5a91f86a5d846de1f
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2065
_reflns_number_total             2268
_reflns_odcompleteness_completeness 100.00
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_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    ?
_refine_diff_density_max         1.540
_refine_diff_density_min         -1.193
_refine_diff_density_rms         0.251
_refine_ls_extinction_coef       0.00049(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         2268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0560
_refine_ls_restrained_S_all      1.070
_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)+(0.1093P)²+6.1869P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1576
_refine_ls_wR_factor_ref         0.1610
_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) groups
2. Others
 Sof(C1GB)=Sof(H1GC)=Sof(H1GD)=0.5*(1-FVAR(2))
 Sof(C1GA)=Sof(H1GA)=Sof(H1GB)=0.5*FVAR(2)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C1(H1A,H1B), C1GA(H1GA,H1GB), C1GB(H1GC,H1GD)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C6(H6), C3(H3)
;
_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
Br3 Br 0.40861(2) 0.63126(5) 0.63818(6) 0.0274(3) Uani 1 1 d . . . . .
Br1 Br 0.44761(3) 0.17116(5) 0.10539(7) 0.0305(3) Uani 1 1 d . . . . .
Br2 Br 0.23895(3) 0.57571(7) 0.03976(8) 0.0440(3) Uani 1 1 d . . . . .
N1 N 0.4091(2) 0.5437(4) 0.2964(5) 0.0293(11) Uani 1 1 d . . . . .
H1 H 0.412386 0.568506 0.387547 0.035 Uiso 1 1 calc R . . . .
C2 C 0.4413(2) 0.4189(5) 0.1020(6) 0.0233(11) Uani 1 1 d . . . . .
Cl1G Cl 0.31174(10) 0.2546(4) 0.2921(5) 0.1062(12) Uani 1 1 d . . . . .
C4 C 0.3681(3) 0.5880(5) 0.2115(7) 0.0275(11) Uani 1 1 d . . . . .
H4 H 0.343539 0.644425 0.251344 0.033 Uiso 1 1 calc R . . . .
C7 C 0.3159(3) 0.6066(6) -0.0340(8) 0.0396(15) Uani 1 1 d . . . . .
H7A H 0.319373 0.576338 -0.135821 0.048 Uiso 1 1 calc R . . . .
H7B H 0.322079 0.690786 -0.037631 0.048 Uiso 1 1 calc R . . . .
C5 C 0.3610(2) 0.5513(5) 0.0633(6) 0.0238(11) Uani 1 1 d . . . . .
C6 C 0.3983(2) 0.4645(5) 0.0107(6) 0.0236(10) Uani 1 1 d . . . . .
H6 H 0.394358 0.436835 -0.087320 0.028 Uiso 1 1 calc R . . . .
C3 C 0.4459(2) 0.4619(5) 0.2476(6) 0.0244(11) Uani 1 1 d . . . . .
H3 H 0.474577 0.434106 0.311149 0.029 Uiso 1 1 calc R . . . .
C1 C 0.4802(2) 0.3246(5) 0.0499(7) 0.0282(12) Uani 1 1 d . . . . .
H1A H 0.517593 0.334013 0.096114 0.034 Uiso 1 1 calc R . . . .
H1B H 0.484833 0.329181 -0.058623 0.034 Uiso 1 1 calc R . . . .
C1GA C 0.250000 0.250000 0.391(2) 0.073(6) Uani 0.77(4) 2 d S T P A 1
H1GA H 0.251214 0.181436 0.455569 0.088 Uiso 0.387(18) 1 calc R . . A 1
H1GB H 0.248786 0.318566 0.455566 0.088 Uiso 0.387(18) 1 calc R . . A 1
C1GB C 0.250000 0.250000 0.229(7) 0.11(4) Uani 0.23(4) 2 d S T P A 2
H1GC H 0.248803 0.317587 0.162201 0.127 Uiso 0.113(18) 1 calc R . . A 2
H1GD H 0.251196 0.182416 0.162196 0.127 Uiso 0.113(18) 1 calc R . . A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.967(6) . ?
Br2 C7 1.941(7) . ?
N1 C4 1.318(8) . ?
N1 C3 1.338(7) . ?
C2 C6 1.389(8) . ?
C2 C3 1.386(7) . ?
C2 C1 1.480(8) . ?
Cl1G C1GA 1.686(9) . ?
Cl1G C1GB 1.55(2) . ?
C4 C5 1.390(8) . ?
C7 C5 1.500(8) . ?
C5 C6 1.397(8) . ?

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
C4 N1 C3 123.1(5) . . ?
C6 C2 C1 122.1(5) . . ?
C3 C2 C6 117.9(5) . . ?
C3 C2 C1 120.0(5) . . ?
N1 C4 C5 120.8(5) . . ?
C5 C7 Br2 112.2(4) . . ?
C4 C5 C7 120.2(5) . . ?
C4 C5 C6 117.0(5) . . ?
C6 C5 C7 122.8(5) . . ?
C2 C6 C5 121.3(5) . . ?
N1 C3 C2 119.8(5) . . ?
C2 C1 Br1 109.2(4) . . ?
Cl1G C1GA Cl1G 117.5(10) 2 . ?
Cl1G C1GB Cl1G 137(4) 2 . ?

_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 4.422
_oxdiff_exptl_absorpt_empirical_full_min 0.326
####################################################################### 
# 
# 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_DCM_198K
_database_code_depnum_ccdc_archive 'CCDC 2124415'
loop_
_audit_author_name
_audit_author_address
'Shohei Tashiro'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C7 H8 Br2 N, C0.5 H Cl'
_chemical_formula_sum            'C7.50 H9 Br3 Cl N'
_chemical_formula_weight         388.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNBrCl
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   23.3007(2)
_cell_length_b                   11.41420(10)
_cell_length_c                   8.88690(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2363.55(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5101
_cell_measurement_temperature    198
_cell_measurement_theta_max      71.5540
_cell_measurement_theta_min      4.2970
_shelx_estimated_absorpt_T_max   0.672
_shelx_estimated_absorpt_T_min   0.161
_exptl_absorpt_coefficient_mu    14.383
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    2.183
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7220
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.875
_diffrn_reflns_theta_min         3.794
_diffrn_ambient_temperature      198
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00  -1.00   0.50    0.50    --    0.00 -38.00 120.00   84
  2  ω    -20.00  40.00   0.50    0.50    --    0.00  38.00   0.00  120
  3  ω     36.00 132.00   0.50    0.50    --   95.70 -82.00-180.00  192
  4  ω     77.00 102.00   0.50    0.50    --   95.70 -45.00 150.00   50
  5  ω    124.00 184.00   0.50    0.50    --   95.70  30.00  60.00  120
  6  ω     64.00  90.00   0.50    0.50    --   95.70  30.00  60.00   52
  7  ω      6.00  61.00   0.50    0.50    --   95.70 -45.00 150.00  110
  8  ω     32.00  94.00   0.50    0.50    --   95.70 -77.00  90.00  124
  9  ω     42.00 115.00   0.50    0.50    --   95.70  15.00  30.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0650580000
_diffrn_orient_matrix_UB_12      -0.0219840000
_diffrn_orient_matrix_UB_13      0.0118838000
_diffrn_orient_matrix_UB_21      -0.0103454000
_diffrn_orient_matrix_UB_22      0.1327148000
_diffrn_orient_matrix_UB_23      0.0158761000
_diffrn_orient_matrix_UB_31      -0.0054883000
_diffrn_orient_matrix_UB_32      0.0106976000
_diffrn_orient_matrix_UB_33      -0.1722753000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2115
_reflns_number_total             2272
_reflns_odcompleteness_completeness 99.84
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    ?
_refine_diff_density_max         1.127
_refine_diff_density_min         -1.378
_refine_diff_density_rms         0.168
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.061
_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)+(0.0770P)²+6.3776P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1237
_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) groups
2. Others
 Sof(C1GA)=Sof(H1GC)=Sof(H1GD)=0.5*(1-FVAR(2))
 Sof(C1GB)=Sof(H1GA)=Sof(H1GB)=0.5*FVAR(2)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C1(H1A,H1B), C1GB(H1GA,H1GB), C1GA(H1GC,H1GD)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C6(H6), C3(H3)
;
_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
Br3 Br 0.59134(2) 0.63099(4) 1.13733(5) 0.03232(19) Uani 1 1 d . . . . .
Br2 Br 0.55308(2) 0.17157(4) 0.60546(6) 0.03542(19) Uani 1 1 d . . . . .
Br1 Br 0.76105(2) 0.57667(6) 0.53911(7) 0.0527(2) Uani 1 1 d . . . . .
Cl1G Cl 0.68858(10) 0.2277(3) 0.3242(5) 0.1259(12) Uani 1 1 d . . . . .
N1 N 0.59056(16) 0.5442(4) 0.7961(4) 0.0326(9) Uani 1 1 d . . . . .
H1 H 0.587157 0.569381 0.889276 0.039 Uiso 1 1 calc R . . . .
C5 C 0.55894(18) 0.4190(4) 0.6024(5) 0.0282(9) Uani 1 1 d . . . . .
C4 C 0.55370(19) 0.4629(4) 0.7471(5) 0.0297(9) Uani 1 1 d . . . . .
H4 H 0.524035 0.435305 0.811270 0.036 Uiso 1 1 calc R . . . .
C2 C 0.63893(19) 0.5507(4) 0.5636(5) 0.0293(9) Uani 1 1 d . . . . .
C6 C 0.60245(19) 0.4646(4) 0.5109(5) 0.0284(9) Uani 1 1 d . . . . .
H6 H 0.606955 0.435896 0.411224 0.034 Uiso 1 1 calc R . . . .
C7 C 0.5200(2) 0.3232(4) 0.5504(6) 0.0325(10) Uani 1 1 d . . . . .
H7A H 0.515068 0.327722 0.439841 0.039 Uiso 1 1 calc R . . . .
H7B H 0.481762 0.332196 0.597761 0.039 Uiso 1 1 calc R . . . .
C3 C 0.6321(2) 0.5890(4) 0.7109(5) 0.0317(9) Uani 1 1 d . . . . .
H3 H 0.657110 0.647017 0.750780 0.038 Uiso 1 1 calc R . . . .
C1 C 0.6837(2) 0.6065(6) 0.4674(6) 0.0471(13) Uani 1 1 d . . . . .
H1A H 0.677080 0.692123 0.464614 0.056 Uiso 1 1 calc R . . . .
H1B H 0.680035 0.576383 0.363351 0.056 Uiso 1 1 calc R . . . .
C1GB C 0.750000 0.250000 0.229(2) 0.117(11) Uani 0.65(3) 2 d S T P A 1
H1GA H 0.755986 0.181364 0.162288 0.140 Uiso 0.325(17) 1 calc R . . A 1
H1GB H 0.744015 0.318633 0.162282 0.140 Uiso 0.325(17) 1 calc R . . A 1
C1GA C 0.750000 0.250000 0.395(6) 0.13(2) Uani 0.35(3) 2 d S T P A 2
H1GC H 0.744075 0.317945 0.462824 0.150 Uiso 0.175(17) 1 calc R . . A 2
H1GD H 0.755926 0.182050 0.462816 0.150 Uiso 0.175(17) 1 calc R . . A 2


_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
Br2 C7 1.958(5) . ?
Br1 C1 1.941(5) . ?
Cl1G C1GB 1.684(10) . ?
Cl1G C1GA 1.59(2) . ?
N1 H1 0.8800 . ?
N1 C4 1.337(6) . ?
N1 C3 1.332(6) . ?
C5 C4 1.385(6) . ?
C5 C6 1.400(6) . ?
C5 C7 1.495(6) . ?
C4 H4 0.9500 . ?
C2 C6 1.381(6) . ?
C2 C3 1.389(7) . ?
C2 C1 1.492(6) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C3 H3 0.9500 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1GB H1GA 0.9900 . ?
C1GB H1GB 0.9900 . ?
C1GA H1GC 0.9900 . ?
C1GA H1GD 0.9900 . ?

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
C4 N1 H1 118.4 . . ?
C3 N1 H1 118.4 . . ?
C3 N1 C4 123.3(4) . . ?
C4 C5 C6 118.0(4) . . ?
C4 C5 C7 119.9(4) . . ?
C6 C5 C7 122.1(4) . . ?
N1 C4 C5 119.8(4) . . ?
N1 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C2 C3 118.3(4) . . ?
C6 C2 C1 122.7(4) . . ?
C3 C2 C1 119.0(4) . . ?
C5 C6 H6 119.6 . . ?
C2 C6 C5 120.9(4) . . ?
C2 C6 H6 119.6 . . ?
Br2 C7 H7A 109.8 . . ?
Br2 C7 H7B 109.8 . . ?
C5 C7 Br2 109.3(3) . . ?
C5 C7 H7A 109.8 . . ?
C5 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
N1 C3 C2 119.9(4) . . ?
N1 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
Br1 C1 H1A 109.0 . . ?
Br1 C1 H1B 109.0 . . ?
C2 C1 Br1 112.7(3) . . ?
C2 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
Cl1G C1GB Cl1G 119.4(12) 2_655 . ?
Cl1G C1GB H1GA 107.5 2_655 . ?
Cl1G C1GB H1GA 107.5 . . ?
Cl1G C1GB H1GB 107.5 2_655 . ?
Cl1G C1GB H1GB 107.5 . . ?
H1GA C1GB H1GB 107.0 . . ?
Cl1G C1GA Cl1G 133(4) 2_655 . ?
Cl1G C1GA H1GC 104.0 2_655 . ?
Cl1G C1GA H1GC 104.0 . . ?
Cl1G C1GA H1GD 104.0 2_655 . ?
Cl1G C1GA H1GD 104.0 . . ?
H1GC C1GA H1GD 105.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C3 C2 -0.4(7) . . . . ?
C4 C5 C6 C2 -0.1(7) . . . . ?
C4 C5 C7 Br2 -87.0(5) . . . . ?
C6 C5 C4 N1 -1.6(7) . . . . ?
C6 C5 C7 Br2 90.9(5) . . . . ?
C6 C2 C3 N1 -1.2(7) . . . . ?
C6 C2 C1 Br1 -116.7(5) . . . . ?
C7 C5 C4 N1 176.5(4) . . . . ?
C7 C5 C6 C2 -178.0(4) . . . . ?
C3 N1 C4 C5 1.8(7) . . . . ?
C3 C2 C6 C5 1.4(7) . . . . ?
C3 C2 C1 Br1 65.4(6) . . . . ?
C1 C2 C6 C5 -176.5(4) . . . . ?
C1 C2 C3 N1 176.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.385
_oxdiff_exptl_absorpt_empirical_full_min 0.620
####################################################################### 
# 
# 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_DBM_148K
_database_code_depnum_ccdc_archive 'CCDC 2124430'
loop_
_audit_author_name
_audit_author_address
'Shohei Tashiro'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C7 H8 Br2 N, C0.5 H Br'
_chemical_formula_sum            'C7.50 H9 Br4 N'
_chemical_formula_weight         432.80
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNBr
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   23.5252(4)
_cell_length_b                   11.2799(2)
_cell_length_c                   8.9163(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2366.05(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4050
_cell_measurement_temperature    148
_cell_measurement_theta_max      71.7050
_cell_measurement_theta_min      3.8400
_shelx_estimated_absorpt_T_max   0.737
_shelx_estimated_absorpt_T_min   0.085
_exptl_absorpt_coefficient_mu    16.248
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23454
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
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    2.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1608
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7415
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.205
_diffrn_reflns_theta_min         3.758
_diffrn_ambient_temperature      148
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00  20.00   0.50    0.50    --    0.00 -38.00  60.00  148
  2  ω     10.00  41.00   0.50    0.50    --    0.00  38.00  90.00   62
  3  ω    102.00 131.00   0.50    0.83    --   95.70  45.00-150.00   58
  4  ω     81.00 114.00   0.50    0.83    --   95.70 -82.00 -30.00   66
  5  ω     35.00  73.00   0.50    0.83    --   95.70 -82.00 -30.00   76
  6  ω    134.00 178.00   0.50    0.83    --   95.70  45.00-150.00   88
  7  ω     31.00 130.00   0.50    0.83    --   95.70 -82.00-120.00  198
  8  ω     69.00 103.00   0.50    0.83    --   95.70 -82.00 -90.00   68
  9  ω     64.00 185.00   0.50    0.83    --   95.70  30.00 150.00  242
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0528830000
_diffrn_orient_matrix_UB_12      0.0798973000
_diffrn_orient_matrix_UB_13      -0.0131568000
_diffrn_orient_matrix_UB_21      0.0385642000
_diffrn_orient_matrix_UB_22      0.1102132000
_diffrn_orient_matrix_UB_23      -0.0084339000
_diffrn_orient_matrix_UB_31      0.0021615000
_diffrn_orient_matrix_UB_32      -0.0114192000
_diffrn_orient_matrix_UB_33      -0.1720334000
_diffrn_oxdiff_digest_frames     
;
01f9eb994db1eae252530f2466fbb0bdd2000297d92
;
_diffrn_oxdiff_digest_hkl        
;
01632695d8434b2ed382ccaab02cdd6b4bd800
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2066
_reflns_number_total             2286
_reflns_odcompleteness_completeness 99.76
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_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    ?
_refine_diff_density_max         1.532
_refine_diff_density_min         -1.095
_refine_diff_density_rms         0.240
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         2286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.034
_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)+(0.0762P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1173
_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) groups
2. Others
 Fixed Sof: H1GA(0.5) H1GB(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C1G(H1GA,H1GB), C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C6(H6), C4(H4)
;
_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
Br3 Br 0.40817(2) 0.62951(5) 0.64051(5) 0.02535(18) Uani 1 1 d . . . . .
Br1 Br 0.45056(2) 0.17162(4) 0.10566(6) 0.02684(18) Uani 1 1 d . . . . .
Br2 Br 0.24050(2) 0.57382(6) 0.04353(6) 0.0354(2) Uani 1 1 d . . . . .
Br1G Br 0.31790(2) 0.24564(6) 0.27477(7) 0.0431(2) Uani 1 1 d . . . . .
N1 N 0.40927(16) 0.5422(4) 0.3001(5) 0.0276(9) Uani 1 1 d . . . . .
H1 H 0.412192 0.565476 0.393998 0.033 Uiso 1 1 calc R . . . .
C2 C 0.44184(18) 0.4219(4) 0.1027(5) 0.0214(9) Uani 1 1 d . . . . .
C3 C 0.44650(19) 0.4624(4) 0.2487(5) 0.0247(9) Uani 1 1 d . . . . .
H3 H 0.475946 0.433687 0.311908 0.030 Uiso 1 1 calc R . . . .
C5 C 0.36156(19) 0.5529(4) 0.0677(5) 0.0238(9) Uani 1 1 d . . . . .
C6 C 0.39928(18) 0.4678(4) 0.0124(5) 0.0221(9) Uani 1 1 d . . . . .
H6 H 0.395703 0.441234 -0.088247 0.027 Uiso 1 1 calc R . . . .
C4 C 0.36774(19) 0.5886(4) 0.2157(5) 0.0257(9) Uani 1 1 d . . . . .
H4 H 0.342583 0.645786 0.257068 0.031 Uiso 1 1 calc R . . . .
C1 C 0.4820(2) 0.3279(4) 0.0484(5) 0.0258(10) Uani 1 1 d . . . . .
H1A H 0.519892 0.339042 0.094490 0.031 Uiso 1 1 calc R . . . .
H1B H 0.486147 0.332764 -0.061887 0.031 Uiso 1 1 calc R . . . .
C1G C 0.250000 0.250000 0.3952(9) 0.0393(18) Uani 1 2 d S T P . .
H1GA H 0.251047 0.320915 0.460532 0.047 Uiso 0.5 1 calc R . . . .
H1GB H 0.248954 0.179083 0.460529 0.047 Uiso 0.5 1 calc R . . . .
C7 C 0.3173(2) 0.6086(5) -0.0289(6) 0.0312(11) Uani 1 1 d . . . . .
H7A H 0.321405 0.578818 -0.132825 0.037 Uiso 1 1 calc R . . . .
H7B H 0.323102 0.695525 -0.030667 0.037 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
Br1 C1 1.978(5) . ?
Br2 C7 1.959(5) . ?
Br1G C1G 1.925(5) . ?
N1 C3 1.338(6) . ?
N1 C4 1.339(6) . ?
C2 C3 1.384(7) . ?
C2 C6 1.386(6) . ?
C2 C1 1.500(6) . ?
C5 C6 1.397(6) . ?
C5 C4 1.387(6) . ?
C5 C7 1.490(6) . ?

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
C3 N1 C4 123.2(4) . . ?
C3 C2 C6 118.7(4) . . ?
C3 C2 C1 119.1(4) . . ?
C6 C2 C1 122.2(4) . . ?
N1 C3 C2 119.5(4) . . ?
C6 C5 C7 121.9(4) . . ?
C4 C5 C6 117.9(4) . . ?
C4 C5 C7 120.1(4) . . ?
C2 C6 C5 120.7(4) . . ?
N1 C4 C5 119.8(4) . . ?
C2 C1 Br1 108.1(3) . . ?
Br1G C1G Br1G 112.2(4) . 2 ?
C5 C7 Br2 111.7(3) . . ?

_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 4.293
_oxdiff_exptl_absorpt_empirical_full_min 0.323
####################################################################### 
# 
# 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_DCM_183K
_database_code_depnum_ccdc_archive 'CCDC 2124431'
loop_
_audit_author_name
_audit_author_address
'Shohei Tashiro'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C7 H8 Br2 N, C0.5 H Cl'
_chemical_formula_sum            'C7.50 H9 Br3 Cl N'
_chemical_formula_weight         388.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNBrCl
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   23.3030(2)
_cell_length_b                   11.39340(10)
_cell_length_c                   8.87830(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2357.19(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5038
_cell_measurement_temperature    183
_cell_measurement_theta_max      71.4930
_cell_measurement_theta_min      3.8020
_shelx_estimated_absorpt_T_max   0.672
_shelx_estimated_absorpt_T_min   0.161
_exptl_absorpt_coefficient_mu    14.422
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    2.189
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            6936
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.059
_diffrn_reflns_theta_min         3.794
_diffrn_ambient_temperature      183
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  85.00   0.50    0.50    --    0.00  77.00 -60.00  238
  2  ω      8.00  33.00   0.50    0.50    --    0.00  57.00 -90.00   50
  3  ω     53.00 119.00   0.50    0.50    --   95.70 -82.00-180.00  132
  4  ω     90.00 121.00   0.50    0.50    --   95.70 -30.00   0.00   62
  5  ω     56.00  84.00   0.50    0.50    --   95.70 -61.00-180.00   56
  6  ω      7.00  52.00   0.50    0.50    --   95.70 -61.00-180.00   90
  7  ω     23.00  76.00   0.50    0.50    --   95.70 -30.00   0.00  106
  8  ω     88.00 116.00   0.50    0.50    --   95.70 -61.00-180.00   56
  9  ω     16.00 126.00   0.50    0.50    --   95.70 -30.00-120.00  220
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0650691000
_diffrn_orient_matrix_UB_12      0.0218026000
_diffrn_orient_matrix_UB_13      -0.0118176000
_diffrn_orient_matrix_UB_21      -0.0102425000
_diffrn_orient_matrix_UB_22      -0.1329939000
_diffrn_orient_matrix_UB_23      -0.0158422000
_diffrn_orient_matrix_UB_31      -0.0054656000
_diffrn_orient_matrix_UB_32      -0.0107282000
_diffrn_orient_matrix_UB_33      0.1724520000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2126
_reflns_number_total             2273
_reflns_odcompleteness_completeness 99.92
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    ?
_refine_diff_density_max         1.086
_refine_diff_density_min         -1.263
_refine_diff_density_rms         0.168
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.117
_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)+(0.0716P)²+8.3041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1272
_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) groups
2. Others
 Sof(C1GB)=Sof(H1GC)=Sof(H1GD)=0.5*(1-FVAR(2))
 Sof(C1GA)=Sof(H1GA)=Sof(H1GB)=0.5*FVAR(2)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C1(H1A,H1B), C1GA(H1GA,H1GB), C1GB(H1GC,H1GD)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C6(H6), C3(H3)
;
_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
Br3 Br 0.40860(2) 0.36882(4) 1.13769(6) 0.02966(19) Uani 1 1 d . . . . .
Br2 Br 0.44724(2) 0.82885(4) 0.60523(6) 0.0327(2) Uani 1 1 d . . . . .
Br1 Br 0.23881(2) 0.42360(6) 0.53958(8) 0.0483(2) Uani 1 1 d . . . . .
Cl1G Cl 0.31148(10) 0.7656(3) 0.3105(5) 0.1296(14) Uani 1 1 d . . . . .
N1 N 0.40922(18) 0.4558(4) 0.7968(5) 0.0307(9) Uani 1 1 d . . . . .
H1 H 0.412695 0.430422 0.890040 0.037 Uiso 1 1 calc R . . . .
C5 C 0.4410(2) 0.5814(4) 0.6022(5) 0.0252(10) Uani 1 1 d . . . . .
C4 C 0.4461(2) 0.5371(4) 0.7468(5) 0.0266(10) Uani 1 1 d . . . . .
H4 H 0.475854 0.564523 0.810839 0.032 Uiso 1 1 calc R . . . .
C2 C 0.3608(2) 0.4494(4) 0.5634(5) 0.0278(10) Uani 1 1 d . . . . .
C6 C 0.3978(2) 0.5355(4) 0.5106(5) 0.0265(9) Uani 1 1 d . . . . .
H6 H 0.393680 0.563670 0.410506 0.032 Uiso 1 1 calc R . . . .
C7 C 0.4802(2) 0.6760(4) 0.5492(6) 0.0299(10) Uani 1 1 d . . . . .
H7A H 0.484875 0.671341 0.438561 0.036 Uiso 1 1 calc R . . . .
H7B H 0.518496 0.666636 0.596251 0.036 Uiso 1 1 calc R . . . .
C3 C 0.3674(2) 0.4116(4) 0.7110(6) 0.0304(10) Uani 1 1 d . . . . .
H3 H 0.342112 0.354078 0.751101 0.036 Uiso 1 1 calc R . . . .
C1 C 0.3160(2) 0.3940(6) 0.4650(7) 0.0417(13) Uani 1 1 d . . . . .
H1A H 0.322677 0.308271 0.460447 0.050 Uiso 1 1 calc R . . . .
H1B H 0.319552 0.425599 0.361524 0.050 Uiso 1 1 calc R . . . .
C1GA C 0.250000 0.750000 0.392(3) 0.076(9) Uani 0.50(3) 2 d S T P A 1
H1GA H 0.254175 0.681090 0.458679 0.091 Uiso 0.248(16) 1 calc R . . A 1
H1GB H 0.245825 0.818909 0.458679 0.091 Uiso 0.248(16) 1 calc R . . A 1
C1GB C 0.250000 0.750000 0.232(3) 0.107(13) Uani 0.50(3) 2 d S T P A 2
H1GC H 0.245830 0.818836 0.164857 0.128 Uiso 0.252(16) 1 calc R . . A 2
H1GD H 0.254170 0.681163 0.164858 0.128 Uiso 0.252(16) 1 calc R . . A 2


_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
Br2 C7 1.967(5) . ?
Br1 C1 1.946(6) . ?
Cl1G C1GA 1.613(13) . ?
Cl1G C1GB 1.603(13) . ?
N1 H1 0.8800 . ?
N1 C4 1.339(6) . ?
N1 C3 1.336(7) . ?
C5 C4 1.384(7) . ?
C5 C6 1.396(7) . ?
C5 C7 1.490(7) . ?
C4 H4 0.9500 . ?
C2 C6 1.388(7) . ?
C2 C3 1.388(7) . ?
C2 C1 1.500(7) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C3 H3 0.9500 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1GA H1GA 0.9900 . ?
C1GA H1GB 0.9900 . ?
C1GB H1GC 0.9900 . ?
C1GB H1GD 0.9900 . ?

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
C4 N1 H1 118.7 . . ?
C3 N1 H1 118.7 . . ?
C3 N1 C4 122.6(4) . . ?
C4 C5 C6 117.7(4) . . ?
C4 C5 C7 120.3(4) . . ?
C6 C5 C7 122.0(4) . . ?
N1 C4 C5 120.4(4) . . ?
N1 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C2 C3 118.0(4) . . ?
C6 C2 C1 122.2(5) . . ?
C3 C2 C1 119.8(5) . . ?
C5 C6 H6 119.4 . . ?
C2 C6 C5 121.1(5) . . ?
C2 C6 H6 119.4 . . ?
Br2 C7 H7A 109.9 . . ?
Br2 C7 H7B 109.9 . . ?
C5 C7 Br2 108.7(3) . . ?
C5 C7 H7A 109.9 . . ?
C5 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
N1 C3 C2 120.2(4) . . ?
N1 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
Br1 C1 H1A 109.3 . . ?
Br1 C1 H1B 109.3 . . ?
C2 C1 Br1 111.8(4) . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 107.9 . . ?
Cl1G C1GA Cl1G 127.0(18) 2_565 . ?
Cl1G C1GA H1GA 105.6 2_565 . ?
Cl1G C1GA H1GA 105.6 . . ?
Cl1G C1GA H1GB 105.6 2_565 . ?
Cl1G C1GA H1GB 105.6 . . ?
H1GA C1GA H1GB 106.1 . . ?
Cl1G C1GB Cl1G 128.4(18) 2_565 . ?
Cl1G C1GB H1GC 105.2 2_565 . ?
Cl1G C1GB H1GC 105.2 . . ?
Cl1G C1GB H1GD 105.2 2_565 . ?
Cl1G C1GB H1GD 105.2 . . ?
H1GC C1GB H1GD 105.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.756
_oxdiff_exptl_absorpt_empirical_full_min 0.653
####################################################################### 
# 
# 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_From_TCE
_database_code_depnum_ccdc_archive 'CCDC 2124418'
loop_
_audit_author_name
_audit_author_address
'Shohei Tashiro'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.29(C7 H8 Br2 N), 0.29(Br)'
_chemical_formula_sum            'C2.05 H2.34 Br0.88 N0.29'
_chemical_formula_weight         101.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNBrCl
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   14.72130(10)
_cell_length_b                   8.57480(10)
_cell_length_c                   23.2614(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.0110(10)
_cell_angle_gamma                90
_cell_volume                     2929.15(5)
_cell_formula_units_Z            41
_cell_measurement_reflns_used    19575
_cell_measurement_temperature    93
_cell_measurement_theta_max      71.9530
_cell_measurement_theta_min      3.4270
_shelx_estimated_absorpt_T_max   0.524
_shelx_estimated_absorpt_T_min   0.155
_exptl_absorpt_coefficient_mu    14.833
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    2.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1944
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            10320
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.360
_diffrn_reflns_theta_min         3.447
_diffrn_ambient_temperature      93
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00  27.00   0.50    0.50    --    0.00 -38.00 120.00  232
  2  ω    -28.00  89.00   0.50    0.50    --    0.00  57.00   0.00  234
  3  ω    -27.00  89.00   0.50    0.50    --    0.00  38.00  90.00  232
  4  ω     64.00 185.00   0.50    0.50    --   95.70  30.00 -30.00  242
  5  ω      6.00 122.00   0.50    0.50    --   95.70 -45.00-150.00  232
  6  ω      6.00 125.00   0.50    0.50    --   95.70 -61.00 150.00  238
  7  ω      6.00 132.00   0.50    0.50    --   95.70 -82.00  60.00  252
  8  ω     64.00 185.00   0.50    0.50    --   95.70  30.00   0.00  242
  9  ω      6.00 125.00   0.50    0.50    --   95.70 -61.00  60.00  238
 10  ω     69.00 185.00   0.50    0.50    --   95.70  45.00-120.00  232
 11  ω     64.00 185.00   0.50    0.50    --   95.70  30.00 -90.00  242
 12  ω    -27.00  89.00   0.50    0.50    --    0.00  38.00 -30.00  232
 13  ω    -28.00  89.00   0.50    0.50    --    0.00  57.00-120.00  234
 14  ω     64.00 151.00   0.50    0.50    --   95.70  30.00 150.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0874228000
_diffrn_orient_matrix_UB_12      0.0707150000
_diffrn_orient_matrix_UB_13      0.0218220000
_diffrn_orient_matrix_UB_21      0.0151893000
_diffrn_orient_matrix_UB_22      -0.0934384000
_diffrn_orient_matrix_UB_23      0.0563600000
_diffrn_orient_matrix_UB_31      0.0558221000
_diffrn_orient_matrix_UB_32      0.1362390000
_diffrn_orient_matrix_UB_33      0.0274622000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9641
_reflns_number_total             10320
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 _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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    ?
_refine_diff_density_max         1.667
_refine_diff_density_min         -1.434
_refine_diff_density_rms         0.324
_refine_ls_extinction_coef       0.00021(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         10320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.109
_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)+(0.1144P)²+1.4275P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1453
_refine_ls_wR_factor_ref         0.1470
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5485(11)
 0.4515(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C15(H15A,H15B), C21(H21A,H21B), C14(H14A,H14B), C1(H1A,H1B),
 C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), N2(H2), C4(H4), C20(H20), C17(H17), C13(H13), C6(H6),
 C10(H10), C3(H3A), C11(H11), C18(H18)
;
_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
Br8 Br 0.62387(4) 0.58614(7) 0.42078(3) 0.01558(17) Uani 1 1 d . . . . .
Br4 Br 0.41287(4) 0.38645(7) 0.40579(3) 0.01666(17) Uani 1 1 d . . . . .
Br5 Br 0.13976(4) -0.09221(7) 0.57870(3) 0.01672(17) Uani 1 1 d . . . . .
Br3 Br 0.29509(4) -0.02562(7) 0.24946(3) 0.01647(17) Uani 1 1 d . . . . .
Br9 Br 0.44168(4) 0.02937(7) 0.60105(3) 0.01791(18) Uani 1 1 d . . . . .
Br7 Br 0.93161(4) 0.11429(8) 0.61051(3) 0.01985(18) Uani 1 1 d . . . . .
Br2 Br 0.50901(4) 0.74757(7) 0.20881(3) 0.01734(18) Uani 1 1 d . . . . .
Br6 Br -0.08421(4) 0.48021(7) 0.40084(3) 0.01928(18) Uani 1 1 d . . . . .
Br1 Br 0.77291(4) 0.29696(8) 0.20753(3) 0.02201(18) Uani 1 1 d . . . . .
N1 N 0.4740(3) 0.1890(6) 0.2604(2) 0.0169(10) Uani 1 1 d . . . . .
H1 H 0.436228 0.109898 0.255214 0.020 Uiso 1 1 calc R . . . .
N3 N 0.6189(3) 0.2083(6) 0.5702(2) 0.0165(10) Uani 1 1 d . . . . .
H3 H 0.572218 0.164978 0.585658 0.020 Uiso 1 1 calc R . . . .
N2 N 0.0976(3) 0.2885(6) 0.4307(2) 0.0162(10) Uani 1 1 d . . . . .
H2 H 0.046461 0.329288 0.415735 0.019 Uiso 1 1 calc R . . . .
C4 C 0.4386(4) 0.3361(8) 0.2605(2) 0.0180(12) Uani 1 1 d . . . . .
H4 H 0.374690 0.352035 0.255051 0.022 Uiso 1 1 calc R . . . .
C20 C 0.7623(4) 0.3401(7) 0.5218(2) 0.0140(11) Uani 1 1 d . . . . .
H20 H 0.812790 0.385997 0.504903 0.017 Uiso 1 1 calc R . . . .
C5 C 0.4967(4) 0.4611(7) 0.2687(2) 0.0168(12) Uani 1 1 d . . . . .
C9 C 0.2505(4) 0.2175(7) 0.4204(3) 0.0150(11) Uani 1 1 d . . . . .
C17 C 0.6961(4) 0.2252(7) 0.6028(3) 0.0170(12) Uani 1 1 d . . . . .
H17 H 0.699532 0.193137 0.642004 0.020 Uiso 1 1 calc R . . . .
C16 C 0.7716(4) 0.2897(7) 0.5794(2) 0.0141(11) Uani 1 1 d . . . . .
C13 C 0.2546(4) 0.1620(7) 0.4769(2) 0.0141(11) Uani 1 1 d . . . . .
H13 H 0.309353 0.116289 0.493078 0.017 Uiso 1 1 calc R . . . .
C6 C 0.5888(4) 0.4319(7) 0.2771(2) 0.0158(11) Uani 1 1 d . . . . .
H6 H 0.629416 0.517012 0.283816 0.019 Uiso 1 1 calc R . . . .
C8 C 0.3302(4) 0.2135(7) 0.3841(3) 0.0184(12) Uani 1 1 d . . . . .
H8A H 0.308917 0.222594 0.342878 0.022 Uiso 1 1 calc R . . . .
H8B H 0.362770 0.113009 0.389626 0.022 Uiso 1 1 calc R . . . .
C10 C 0.1700(4) 0.2806(7) 0.3978(3) 0.0159(12) Uani 1 1 d . . . . .
H10 H 0.165062 0.318620 0.359351 0.019 Uiso 1 1 calc R . . . .
C3 C 0.5633(4) 0.1588(7) 0.2677(2) 0.0162(11) Uani 1 1 d . . . . .
H3A H 0.584854 0.054435 0.267109 0.019 Uiso 1 1 calc R . . . .
C12 C 0.1801(4) 0.1727(7) 0.5098(2) 0.0149(11) Uani 1 1 d . . . . .
C19 C 0.6804(4) 0.3238(7) 0.4893(2) 0.0141(11) Uani 1 1 d . . . . .
C2 C 0.6239(4) 0.2813(7) 0.2762(2) 0.0159(12) Uani 1 1 d . . . . .
C11 C 0.1010(4) 0.2367(7) 0.4848(3) 0.0162(12) Uani 1 1 d . . . . .
H11 H 0.048609 0.243984 0.506287 0.019 Uiso 1 1 calc R . . . .
C18 C 0.6085(4) 0.2533(7) 0.5154(3) 0.0143(11) Uani 1 1 d . . . . .
H18 H 0.551922 0.237352 0.494003 0.017 Uiso 1 1 calc R . . . .
C15 C 0.8592(4) 0.3052(7) 0.6153(3) 0.0194(12) Uani 1 1 d . . . . .
H15A H 0.846511 0.324724 0.655922 0.023 Uiso 1 1 calc R . . . .
H15B H 0.894042 0.395000 0.601646 0.023 Uiso 1 1 calc R . . . .
C21 C 0.6695(4) 0.3708(7) 0.4276(3) 0.0184(12) Uani 1 1 d . . . . .
H21A H 0.626176 0.299449 0.406371 0.022 Uiso 1 1 calc R . . . .
H21B H 0.728830 0.363092 0.410237 0.022 Uiso 1 1 calc R . . . .
C14 C 0.1840(4) 0.1221(7) 0.5714(3) 0.0180(12) Uani 1 1 d . . . . .
H14A H 0.146394 0.193268 0.593438 0.022 Uiso 1 1 calc R . . . .
H14B H 0.247614 0.128890 0.588159 0.022 Uiso 1 1 calc R . . . .
C1 C 0.7244(4) 0.2533(7) 0.2821(3) 0.0174(12) Uani 1 1 d . . . . .
H1A H 0.737072 0.143743 0.293426 0.021 Uiso 1 1 calc R . . . .
H1B H 0.753416 0.322449 0.312097 0.021 Uiso 1 1 calc R . . . .
C7 C 0.4596(4) 0.6221(7) 0.2698(3) 0.0201(13) Uani 1 1 d . . . . .
H7A H 0.476026 0.670355 0.307820 0.024 Uiso 1 1 calc R . . . .
H7B H 0.392305 0.618852 0.264129 0.024 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
Br8 C21 1.967(6) . ?
Br4 C8 1.962(6) . ?
Br5 C14 1.961(6) . ?
Br7 C15 1.960(6) . ?
Br2 C7 1.961(6) . ?
Br1 C1 1.957(6) . ?
N1 H1 0.8800 . ?
N1 C4 1.366(8) . ?
N1 C3 1.339(8) . ?
N3 H3 0.8800 . ?
N3 C17 1.330(8) . ?
N3 C18 1.330(8) . ?
N2 H2 0.8800 . ?
N2 C10 1.356(7) . ?
N2 C11 1.332(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(8) . ?
C20 H20 0.9500 . ?
C20 C16 1.406(8) . ?
C20 C19 1.383(8) . ?
C5 C6 1.379(8) . ?
C5 C7 1.486(8) . ?
C9 C13 1.395(8) . ?
C9 C8 1.494(8) . ?
C9 C10 1.374(8) . ?
C17 H17 0.9500 . ?
C17 C16 1.387(8) . ?
C16 C15 1.493(8) . ?
C13 H13 0.9500 . ?
C13 C12 1.383(8) . ?
C6 H6 0.9500 . ?
C6 C2 1.391(9) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 H10 0.9500 . ?
C3 H3A 0.9500 . ?
C3 C2 1.383(8) . ?
C12 C11 1.379(8) . ?
C12 C14 1.495(8) . ?
C19 C18 1.395(8) . ?
C19 C21 1.490(8) . ?
C2 C1 1.496(8) . ?
C11 H11 0.9500 . ?
C18 H18 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?

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
C4 N1 H1 118.3 . . ?
C3 N1 H1 118.3 . . ?
C3 N1 C4 123.4(5) . . ?
C17 N3 H3 118.3 . . ?
C18 N3 H3 118.3 . . ?
C18 N3 C17 123.5(5) . . ?
C10 N2 H2 118.7 . . ?
C11 N2 H2 118.7 . . ?
C11 N2 C10 122.5(5) . . ?
N1 C4 H4 120.5 . . ?
N1 C4 C5 119.1(5) . . ?
C5 C4 H4 120.5 . . ?
C16 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C19 C20 C16 120.8(5) . . ?
C4 C5 C6 118.3(6) . . ?
C4 C5 C7 120.0(5) . . ?
C6 C5 C7 121.7(5) . . ?
C13 C9 C8 122.8(5) . . ?
C10 C9 C13 118.3(5) . . ?
C10 C9 C8 118.9(5) . . ?
N3 C17 H17 120.1 . . ?
N3 C17 C16 119.7(6) . . ?
C16 C17 H17 120.1 . . ?
C20 C16 C15 122.0(5) . . ?
C17 C16 C20 118.0(5) . . ?
C17 C16 C15 120.0(5) . . ?
C9 C13 H13 119.5 . . ?
C12 C13 C9 121.0(5) . . ?
C12 C13 H13 119.5 . . ?
C5 C6 H6 119.0 . . ?
C5 C6 C2 121.9(6) . . ?
C2 C6 H6 119.0 . . ?
Br4 C8 H8A 109.8 . . ?
Br4 C8 H8B 109.8 . . ?
C9 C8 Br4 109.5(4) . . ?
C9 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
N2 C10 C9 119.6(5) . . ?
N2 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
N1 C3 H3A 120.4 . . ?
N1 C3 C2 119.3(6) . . ?
C2 C3 H3A 120.4 . . ?
C13 C12 C14 122.1(5) . . ?
C11 C12 C13 118.2(6) . . ?
C11 C12 C14 119.6(5) . . ?
C20 C19 C18 117.7(5) . . ?
C20 C19 C21 122.0(5) . . ?
C18 C19 C21 120.2(5) . . ?
C6 C2 C1 120.9(5) . . ?
C3 C2 C6 118.1(5) . . ?
C3 C2 C1 121.0(6) . . ?
N2 C11 C12 120.4(5) . . ?
N2 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
N3 C18 C19 120.2(5) . . ?
N3 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
Br7 C15 H15A 109.6 . . ?
Br7 C15 H15B 109.6 . . ?
C16 C15 Br7 110.2(4) . . ?
C16 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
Br8 C21 H21A 109.6 . . ?
Br8 C21 H21B 109.6 . . ?
C19 C21 Br8 110.2(4) . . ?
C19 C21 H21A 109.6 . . ?
C19 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
Br5 C14 H14A 109.4 . . ?
Br5 C14 H14B 109.4 . . ?
C12 C14 Br5 111.3(4) . . ?
C12 C14 H14A 109.4 . . ?
C12 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
Br1 C1 H1A 110.1 . . ?
Br1 C1 H1B 110.1 . . ?
C2 C1 Br1 108.0(4) . . ?
C2 C1 H1A 110.1 . . ?
C2 C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
Br2 C7 H7A 109.7 . . ?
Br2 C7 H7B 109.7 . . ?
C5 C7 Br2 109.9(4) . . ?
C5 C7 H7A 109.7 . . ?
C5 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?

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
N1 C4 C5 C6 -0.8(9) . . . . ?
N1 C4 C5 C7 -179.1(5) . . . . ?
N1 C3 C2 C6 0.4(9) . . . . ?
N1 C3 C2 C1 -177.4(5) . . . . ?
N3 C17 C16 C20 2.1(9) . . . . ?
N3 C17 C16 C15 -178.4(5) . . . . ?
C4 N1 C3 C2 0.3(9) . . . . ?
C4 C5 C6 C2 1.6(9) . . . . ?
C4 C5 C7 Br2 -120.7(5) . . . . ?
C20 C16 C15 Br7 -92.6(6) . . . . ?
C20 C19 C18 N3 1.9(9) . . . . ?
C20 C19 C21 Br8 -93.3(6) . . . . ?
C5 C6 C2 C3 -1.4(9) . . . . ?
C5 C6 C2 C1 176.4(5) . . . . ?
C9 C13 C12 C11 1.3(9) . . . . ?
C9 C13 C12 C14 -176.6(5) . . . . ?
C17 N3 C18 C19 -0.6(9) . . . . ?
C17 C16 C15 Br7 87.9(6) . . . . ?
C16 C20 C19 C18 -1.2(9) . . . . ?
C16 C20 C19 C21 -177.7(5) . . . . ?
C13 C9 C8 Br4 -79.0(6) . . . . ?
C13 C9 C10 N2 0.5(9) . . . . ?
C13 C12 C11 N2 -0.9(9) . . . . ?
C13 C12 C14 Br5 -95.3(6) . . . . ?
C6 C5 C7 Br2 61.1(7) . . . . ?
C6 C2 C1 Br1 -78.5(6) . . . . ?
C8 C9 C13 C12 177.8(6) . . . . ?
C8 C9 C10 N2 -178.5(5) . . . . ?
C10 N2 C11 C12 0.3(9) . . . . ?
C10 C9 C13 C12 -1.1(9) . . . . ?
C10 C9 C8 Br4 99.9(6) . . . . ?
C3 N1 C4 C5 -0.1(9) . . . . ?
C3 C2 C1 Br1 99.3(6) . . . . ?
C19 C20 C16 C17 -0.8(9) . . . . ?
C19 C20 C16 C15 179.7(6) . . . . ?
C11 N2 C10 C9 -0.1(9) . . . . ?
C11 C12 C14 Br5 86.8(6) . . . . ?
C18 N3 C17 C16 -1.4(9) . . . . ?
C18 C19 C21 Br8 90.3(6) . . . . ?
C21 C19 C18 N3 178.5(5) . . . . ?
C14 C12 C11 N2 177.1(5) . . . . ?
C7 C5 C6 C2 179.9(5) . . . . ?

_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 3.165
_oxdiff_exptl_absorpt_empirical_full_min 0.661
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5485(11)
2 0.4515(11)

