# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_songmh_1210
_database_code_depnum_ccdc_archive 'CCDC 2084178'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2021-05-17 deposited with the CCDC.	2021-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 Br2 N3'
_chemical_formula_weight         459.18

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   14.62006(16)
_cell_length_b                   5.80584(6)
_cell_length_c                   22.6165(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.1994(11)
_cell_angle_gamma                90
_cell_volume                     1861.08(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    5.573
_shelx_estimated_absorpt_T_min   0.579
_shelx_estimated_absorpt_T_max   0.851
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11202
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.271
_diffrn_reflns_theta_max         76.059
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3576
_reflns_number_gt                3298
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0673P)²+1.7856P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3576
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1229
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.37823(2) 0.61877(7) 0.20785(2) 0.06464(16) Uani 1 1 d . . . . .
Br2 Br -0.41615(3) 0.76599(13) -0.02528(2) 0.1005(2) Uani 1 1 d . . . . .
N1 N 0.01081(17) 0.6898(4) 0.14042(11) 0.0451(5) Uani 1 1 d . . . . .
N2 N -0.0618(2) 0.7999(6) 0.21366(13) 0.0659(8) Uani 1 1 d . . . . .
N3 N -0.07025(17) 0.8209(4) 0.11118(11) 0.0463(5) Uani 1 1 d . . . . .
C1 C 0.0983(2) 0.8008(5) 0.14222(12) 0.0420(6) Uani 1 1 d . . . . .
C2 C 0.1810(2) 0.6869(5) 0.17107(12) 0.0430(6) Uani 1 1 d . . . . .
H2 H 0.178381 0.546320 0.190325 0.052 Uiso 1 1 calc R U . . .
C3 C 0.2668(2) 0.7849(5) 0.17075(13) 0.0468(6) Uani 1 1 d . . . . .
C4 C 0.2740(2) 0.9943(5) 0.14345(14) 0.0545(7) Uani 1 1 d . . . . .
H4 H 0.332577 1.059114 0.144426 0.065 Uiso 1 1 calc R U . . .
C5 C 0.1917(3) 1.1041(5) 0.11472(15) 0.0580(8) Uani 1 1 d . . . . .
H5 H 0.195125 1.244919 0.095762 0.070 Uiso 1 1 calc R U . . .
C6 C 0.1037(2) 1.0110(5) 0.11320(14) 0.0520(7) Uani 1 1 d . . . . .
H6 H 0.049024 1.087613 0.093106 0.062 Uiso 1 1 calc R U . . .
C7 C -0.0063(2) 0.6149(5) 0.19810(14) 0.0462(6) Uani 1 1 d . . . . .
H7A H -0.040882 0.470731 0.193440 0.055 Uiso 1 1 calc R U . . .
H7B H 0.052426 0.596127 0.228885 0.055 Uiso 1 1 calc R U . . .
C8 C -0.1015(2) 0.9366(5) 0.16042(13) 0.0467(6) Uani 1 1 d . . . . .
H8A H -0.078005 1.093463 0.165686 0.056 Uiso 1 1 calc R U . . .
H8B H -0.169783 0.939411 0.152056 0.056 Uiso 1 1 calc R U . . .
C9 C -0.1374(2) 0.6903(5) 0.06808(12) 0.0448(6) Uani 1 1 d . . . . .
C10 C -0.2283(2) 0.7736(6) 0.04634(13) 0.0495(7) Uani 1 1 d . . . . .
H10 H -0.245730 0.913371 0.060432 0.059 Uiso 1 1 calc R U . . .
C11 C -0.2930(3) 0.6473(7) 0.00344(14) 0.0603(8) Uani 1 1 d . . . . .
C12 C -0.2697(3) 0.4432(7) -0.01918(15) 0.0689(10) Uani 1 1 d . . . . .
H12 H -0.314221 0.359708 -0.047540 0.083 Uiso 1 1 calc R U . . .
C13 C -0.1788(4) 0.3647(6) 0.00109(17) 0.0731(11) Uani 1 1 d . . . . .
H13 H -0.161524 0.227673 -0.014490 0.088 Uiso 1 1 calc R U . . .
C14 C -0.1119(3) 0.4856(6) 0.04448(15) 0.0590(8) Uani 1 1 d . . . . .
H14 H -0.050667 0.429763 0.057562 0.071 Uiso 1 1 calc R U . . .
C15 C -0.1004(2) 0.7909(6) 0.26425(13) 0.0481(6) Uani 1 1 d . . . . .
C16 C -0.0780(2) 0.6098(6) 0.30566(14) 0.0530(7) Uani 1 1 d . . . . .
H16 H -0.039797 0.489961 0.298682 0.064 Uiso 1 1 calc R U . . .
C17 C -0.1132(3) 0.6092(7) 0.35754(15) 0.0623(9) Uani 1 1 d . . . . .
H17 H -0.098864 0.487783 0.385080 0.075 Uiso 1 1 calc R U . . .
C18 C -0.1688(3) 0.7868(7) 0.36823(16) 0.0688(10) Uani 1 1 d . . . . .
H18 H -0.191334 0.787132 0.403286 0.083 Uiso 1 1 calc R U . . .
C19 C -0.1911(3) 0.9632(7) 0.32731(17) 0.0687(9) Uani 1 1 d . . . . .
H19 H -0.229289 1.082465 0.334748 0.082 Uiso 1 1 calc R U . . .
C20 C -0.1581(2) 0.9683(6) 0.27500(15) 0.0569(7) Uani 1 1 d . . . . .
H20 H -0.174336 1.088878 0.247348 0.068 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.902(3) . ?
Br2 C11 1.888(4) . ?
N1 C1 1.424(4) . ?
N1 N3 1.427(3) . ?
N1 C7 1.454(4) . ?
N2 C15 1.396(4) . ?
N2 C8 1.440(4) . ?
N2 C7 1.441(4) . ?
N3 C9 1.421(4) . ?
N3 C8 1.466(4) . ?
C1 C2 1.392(4) . ?
C1 C6 1.397(4) . ?
C2 C3 1.379(4) . ?
C3 C4 1.380(4) . ?
C4 C5 1.376(5) . ?
C5 C6 1.388(5) . ?
C9 C10 1.385(4) . ?
C9 C14 1.391(4) . ?
C10 C11 1.387(5) . ?
C11 C12 1.367(6) . ?
C12 C13 1.373(6) . ?
C13 C14 1.393(6) . ?
C15 C20 1.390(5) . ?
C15 C16 1.392(4) . ?
C16 C17 1.392(4) . ?
C17 C18 1.371(6) . ?
C18 C19 1.365(6) . ?
C19 C20 1.383(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
C1 N1 N3 114.2(2) . . ?
C1 N1 C7 117.5(2) . . ?
N3 N1 C7 105.6(2) . . ?
C15 N2 C8 123.0(3) . . ?
C15 N2 C7 122.5(3) . . ?
C8 N2 C7 110.0(2) . . ?
C9 N3 N1 112.9(2) . . ?
C9 N3 C8 118.3(2) . . ?
N1 N3 C8 105.7(2) . . ?
C2 C1 C6 119.5(3) . . ?
C2 C1 N1 118.0(2) . . ?
C6 C1 N1 122.4(3) . . ?
C3 C2 C1 119.2(3) . . ?
C2 C3 C4 122.4(3) . . ?
C2 C3 Br1 118.0(2) . . ?
C4 C3 Br1 119.5(2) . . ?
C5 C4 C3 117.7(3) . . ?
C4 C5 C6 122.0(3) . . ?
C5 C6 C1 119.2(3) . . ?
N2 C7 N1 103.1(2) . . ?
N2 C8 N3 104.2(2) . . ?
C10 C9 C14 119.1(3) . . ?
C10 C9 N3 119.9(3) . . ?
C14 C9 N3 120.9(3) . . ?
C9 C10 C11 119.6(3) . . ?
C12 C11 C10 122.0(4) . . ?
C12 C11 Br2 119.5(3) . . ?
C10 C11 Br2 118.5(3) . . ?
C11 C12 C13 118.2(3) . . ?
C12 C13 C14 121.5(3) . . ?
C9 C14 C13 119.5(4) . . ?
C20 C15 C16 119.6(3) . . ?
C20 C15 N2 120.0(3) . . ?
C16 C15 N2 120.3(3) . . ?
C17 C16 C15 119.7(3) . . ?
C18 C17 C16 120.3(3) . . ?
C19 C18 C17 119.9(3) . . ?
C18 C19 C20 121.3(4) . . ?
C19 C20 C15 119.2(3) . . ?

_refine_diff_density_max         0.680
_refine_diff_density_min         -0.842
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_songmh_1210_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2084179'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2021-05-17 deposited with the CCDC.	2021-07-26 downloaded from the CCDC.
;
_audit_creation_date             2020-12-13
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 Br2 N3'
_chemical_formula_sum            'C20 H17 Br2 N3'
_chemical_formula_weight         459.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   14.62006(16)
_cell_length_b                   5.80584(6)
_cell_length_c                   22.6165(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.1994(11)
_cell_angle_gamma                90
_cell_volume                     1861.08(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9655
_cell_measurement_temperature    294.65(10)
_cell_measurement_theta_max      75.2480
_cell_measurement_theta_min      3.1110
_shelx_estimated_absorpt_T_max   0.851
_shelx_estimated_absorpt_T_min   0.579
_exptl_absorpt_coefficient_mu    5.573
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11202
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.059
_diffrn_reflns_theta_min         3.271
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.65(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.918
_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  36.00   0.50    0.05    --   43.05 -37.00  60.00   54
  2  ω    -11.00  15.00   0.50    0.05    --   43.05 -19.00  90.00   52
  3  ω     36.00  68.00   0.50    0.05    --  109.26 -69.00  72.00   64
  4  ω     44.00  99.00   0.50    0.05    --  109.26 -77.00   0.00  110
  5  ω     56.00 105.00   0.50    0.05    --  109.26 -94.00-120.00   98
  6  ω     38.00  64.00   0.50    0.05    --  109.26 -61.00-150.00   52
  7  ω    105.00 130.00   0.50    0.05    --  109.26  69.00-155.00   50
  8  ω    124.00 150.00   0.50    0.05    --  109.26  45.00 120.00   52
  9  ω     92.00 117.00   0.50    0.05    --  109.26  45.00 120.00   50
 10  ω    -27.00  23.00   0.50    0.05    --   43.05 -19.00 -90.00  100
 11  ω    -67.00  23.00   0.50    0.05    --  -43.05  69.00-155.00  180
 12  ω   -111.00 -18.00   0.50    0.05    --  -43.05 -69.00  72.00  186
 13  ω    -49.00 -24.00   0.50    0.05    -- -100.00  45.00  60.00   50
 14  ω    -54.00 -25.00   0.50    0.05    -- -100.00  45.00   0.00   58
 15  ω    -61.00 -36.00   0.50    0.05    -- -100.00  61.00  60.00   50
 16  ω    -56.00 -31.00   0.50    0.05    -- -100.00  61.00  30.00   50
 17  ω    -67.00 -26.00   0.50    0.05    -- -100.00  77.00 -60.00   82
 18  ω    -85.00 -26.00   0.50    0.05    -- -100.00  69.00-155.00  118
 19  ω    -74.00 -29.00   0.50    0.05    -- -100.00  61.00-180.00   90
 20  ω   -105.00 -76.00   0.50    0.05    -- -100.00  77.00 -60.00   58
 21  ω   -159.00 -76.00   0.50    0.05    -- -100.00 -69.00  72.00  166
 22  ω    -50.00 -24.00   0.50    0.05    -- -100.00  45.00 150.00   52
 23  ω    -74.00 -48.00   0.50    0.05    -- -100.00  61.00 150.00   52
 24  ω   -176.00 -82.00   0.50    0.05    -- -100.00 -45.00 150.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0520381000
_diffrn_orient_matrix_UB_12      -0.1597202000
_diffrn_orient_matrix_UB_13      0.0352729000
_diffrn_orient_matrix_UB_21      -0.0916722000
_diffrn_orient_matrix_UB_22      0.1372509000
_diffrn_orient_matrix_UB_23      -0.0243578000
_diffrn_orient_matrix_UB_31      -0.0264973000
_diffrn_orient_matrix_UB_32      -0.1614224000
_diffrn_orient_matrix_UB_33      -0.0556748000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3298
_reflns_number_total             3576
_reflns_odcompleteness_completeness 98.89
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.842
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3576
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.037
_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)+(0.0673P)²+1.7856P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1229
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C10(H10), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.37823(2) 0.61877(7) 0.20785(2) 0.06464(16) Uani 1 1 d . . . . .
Br2 Br -0.41615(3) 0.76599(13) -0.02528(2) 0.1005(2) Uani 1 1 d . . . . .
N1 N 0.01081(17) 0.6898(4) 0.14042(11) 0.0451(5) Uani 1 1 d . . . . .
N2 N -0.0618(2) 0.7999(6) 0.21366(13) 0.0659(8) Uani 1 1 d . . . . .
N3 N -0.07025(17) 0.8209(4) 0.11118(11) 0.0463(5) Uani 1 1 d . . . . .
C1 C 0.0983(2) 0.8008(5) 0.14222(12) 0.0420(6) Uani 1 1 d . . . . .
C2 C 0.1810(2) 0.6869(5) 0.17107(12) 0.0430(6) Uani 1 1 d . . . . .
H2 H 0.178381 0.546320 0.190325 0.052 Uiso 1 1 calc R . . . .
C3 C 0.2668(2) 0.7849(5) 0.17075(13) 0.0468(6) Uani 1 1 d . . . . .
C4 C 0.2740(2) 0.9943(5) 0.14345(14) 0.0545(7) Uani 1 1 d . . . . .
H4 H 0.332577 1.059114 0.144426 0.065 Uiso 1 1 calc R . . . .
C5 C 0.1917(3) 1.1041(5) 0.11472(15) 0.0580(8) Uani 1 1 d . . . . .
H5 H 0.195125 1.244919 0.095762 0.070 Uiso 1 1 calc R . . . .
C6 C 0.1037(2) 1.0110(5) 0.11320(14) 0.0520(7) Uani 1 1 d . . . . .
H6 H 0.049024 1.087613 0.093106 0.062 Uiso 1 1 calc R . . . .
C7 C -0.0063(2) 0.6149(5) 0.19810(14) 0.0462(6) Uani 1 1 d . . . . .
H7A H -0.040882 0.470731 0.193440 0.055 Uiso 1 1 calc R . . . .
H7B H 0.052426 0.596127 0.228885 0.055 Uiso 1 1 calc R . . . .
C8 C -0.1015(2) 0.9366(5) 0.16042(13) 0.0467(6) Uani 1 1 d . . . . .
H8A H -0.078005 1.093463 0.165686 0.056 Uiso 1 1 calc R . . . .
H8B H -0.169783 0.939411 0.152056 0.056 Uiso 1 1 calc R . . . .
C9 C -0.1374(2) 0.6903(5) 0.06808(12) 0.0448(6) Uani 1 1 d . . . . .
C10 C -0.2283(2) 0.7736(6) 0.04634(13) 0.0495(7) Uani 1 1 d . . . . .
H10 H -0.245730 0.913371 0.060432 0.059 Uiso 1 1 calc R . . . .
C11 C -0.2930(3) 0.6473(7) 0.00344(14) 0.0603(8) Uani 1 1 d . . . . .
C12 C -0.2697(3) 0.4432(7) -0.01918(15) 0.0689(10) Uani 1 1 d . . . . .
H12 H -0.314221 0.359708 -0.047540 0.083 Uiso 1 1 calc R . . . .
C13 C -0.1788(4) 0.3647(6) 0.00109(17) 0.0731(11) Uani 1 1 d . . . . .
H13 H -0.161524 0.227673 -0.014490 0.088 Uiso 1 1 calc R . . . .
C14 C -0.1119(3) 0.4856(6) 0.04448(15) 0.0590(8) Uani 1 1 d . . . . .
H14 H -0.050667 0.429763 0.057562 0.071 Uiso 1 1 calc R . . . .
C15 C -0.1004(2) 0.7909(6) 0.26425(13) 0.0481(6) Uani 1 1 d . . . . .
C16 C -0.0780(2) 0.6098(6) 0.30566(14) 0.0530(7) Uani 1 1 d . . . . .
H16 H -0.039797 0.489961 0.298682 0.064 Uiso 1 1 calc R . . . .
C17 C -0.1132(3) 0.6092(7) 0.35754(15) 0.0623(9) Uani 1 1 d . . . . .
H17 H -0.098864 0.487783 0.385080 0.075 Uiso 1 1 calc R . . . .
C18 C -0.1688(3) 0.7868(7) 0.36823(16) 0.0688(10) Uani 1 1 d . . . . .
H18 H -0.191334 0.787132 0.403286 0.083 Uiso 1 1 calc R . . . .
C19 C -0.1911(3) 0.9632(7) 0.32731(17) 0.0687(9) Uani 1 1 d . . . . .
H19 H -0.229289 1.082465 0.334748 0.082 Uiso 1 1 calc R . . . .
C20 C -0.1581(2) 0.9683(6) 0.27500(15) 0.0569(7) Uani 1 1 d . . . . .
H20 H -0.174336 1.088878 0.247348 0.068 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 C3 1.902(3) . ?
Br2 C11 1.888(4) . ?
N1 N3 1.427(3) . ?
N1 C1 1.424(4) . ?
N1 C7 1.454(4) . ?
N2 C7 1.441(4) . ?
N2 C8 1.440(4) . ?
N2 C15 1.396(4) . ?
N3 C8 1.466(4) . ?
N3 C9 1.421(4) . ?
C1 C2 1.392(4) . ?
C1 C6 1.397(4) . ?
C2 C3 1.379(4) . ?
C3 C4 1.380(4) . ?
C4 C5 1.376(5) . ?
C5 C6 1.388(5) . ?
C9 C10 1.385(4) . ?
C9 C14 1.391(4) . ?
C10 C11 1.387(5) . ?
C11 C12 1.367(6) . ?
C12 C13 1.373(6) . ?
C13 C14 1.393(6) . ?
C15 C16 1.392(4) . ?
C15 C20 1.390(5) . ?
C16 C17 1.392(4) . ?
C17 C18 1.371(6) . ?
C18 C19 1.365(6) . ?
C19 C20 1.383(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
N3 N1 C7 105.6(2) . . ?
C1 N1 N3 114.2(2) . . ?
C1 N1 C7 117.5(2) . . ?
C8 N2 C7 110.0(2) . . ?
C15 N2 C7 122.5(3) . . ?
C15 N2 C8 123.0(3) . . ?
N1 N3 C8 105.7(2) . . ?
C9 N3 N1 112.9(2) . . ?
C9 N3 C8 118.3(2) . . ?
C2 C1 N1 118.0(2) . . ?
C2 C1 C6 119.5(3) . . ?
C6 C1 N1 122.4(3) . . ?
C3 C2 C1 119.2(3) . . ?
C2 C3 Br1 118.0(2) . . ?
C2 C3 C4 122.4(3) . . ?
C4 C3 Br1 119.5(2) . . ?
C5 C4 C3 117.7(3) . . ?
C4 C5 C6 122.0(3) . . ?
C5 C6 C1 119.2(3) . . ?
N2 C7 N1 103.1(2) . . ?
N2 C8 N3 104.2(2) . . ?
C10 C9 N3 119.9(3) . . ?
C10 C9 C14 119.1(3) . . ?
C14 C9 N3 120.9(3) . . ?
C9 C10 C11 119.6(3) . . ?
C10 C11 Br2 118.5(3) . . ?
C12 C11 Br2 119.5(3) . . ?
C12 C11 C10 122.0(4) . . ?
C11 C12 C13 118.2(3) . . ?
C12 C13 C14 121.5(3) . . ?
C9 C14 C13 119.5(4) . . ?
C16 C15 N2 120.3(3) . . ?
C20 C15 N2 120.0(3) . . ?
C20 C15 C16 119.6(3) . . ?
C17 C16 C15 119.7(3) . . ?
C18 C17 C16 120.3(3) . . ?
C19 C18 C17 119.9(3) . . ?
C18 C19 C20 121.3(4) . . ?
C19 C20 C15 119.2(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 1.678
_oxdiff_exptl_absorpt_empirical_full_min 0.680
