# Electronic Supplementary Material (ESI) for ChemComm.
# 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_t_a
_audit_block_doi                 10.5517/ccdc.csd.cc282cd4
_database_code_depnum_ccdc_archive 'CCDC 2087645'
loop_
_audit_author_name
_audit_author_address
'wei ping wu'
;Nan Jing
China
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2021-06-28 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         'C19 H14 Br2 N2'
_chemical_formula_sum            'C19 H14 Br2 N2'
_chemical_formula_weight         430.14

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'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.235(3)
_cell_length_b                   5.7050(11)
_cell_length_c                   18.500(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.660(14)
_cell_angle_gamma                90
_cell_volume                     1690.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      68.33

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   0.5428
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    6.072
_shelx_estimated_absorpt_T_min   0.408
_shelx_estimated_absorpt_T_max   0.463
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16744
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.758
_diffrn_reflns_theta_max         68.276
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3084
_reflns_number_gt                2918
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0249P)²+1.1818P] 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         3084
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0612
_refine_ls_wR_factor_gt          0.0600
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
C1 C 0.01792(13) 0.8939(4) 0.12339(12) 0.0379(5) Uani 1 1 d . . . . .
Br1 Br -0.07366(2) 0.80614(5) 0.03155(2) 0.05582(10) Uani 1 1 d . . . . .
N1 N 0.31988(10) 0.7594(3) 0.37705(9) 0.0317(3) Uani 1 1 d . . . . .
C2 C 0.01291(14) 1.0937(5) 0.16289(14) 0.0484(6) Uani 1 1 d . . . . .
H2 H -0.035929 1.188065 0.145007 0.058 Uiso 1 1 calc R U . . .
Br2 Br 0.73264(2) -0.16716(4) 0.34776(2) 0.03845(9) Uani 1 1 d . . . . .
N2 N 0.31711(10) 0.5188(3) 0.48231(9) 0.0334(4) Uani 1 1 d . . . . .
C5 C 0.15458(14) 0.8186(4) 0.21478(13) 0.0405(5) Uani 1 1 d . . . . .
H5 H 0.203081 0.722766 0.232318 0.049 Uiso 1 1 calc R U . . .
C4 C 0.15215(12) 1.0199(3) 0.25619(11) 0.0319(4) Uani 1 1 d . . . . .
C3 C 0.08031(15) 1.1559(4) 0.22944(14) 0.0435(5) Uani 1 1 d . . . . .
H3 H 0.077124 1.293675 0.257032 0.052 Uiso 1 1 calc R U . . .
C6 C 0.08790(14) 0.7545(4) 0.14858(13) 0.0424(5) Uani 1 1 d . . . . .
H6 H 0.090460 0.616235 0.120937 0.051 Uiso 1 1 calc R U . . .
C7 C 0.22682(13) 1.0924(4) 0.32754(12) 0.0369(4) Uani 1 1 d . . . . .
H7A H 0.271933 1.148540 0.310842 0.044 Uiso 1 1 calc R U . . .
H7B H 0.210390 1.224023 0.353720 0.044 Uiso 1 1 calc R U . . .
C8 C 0.25966(12) 0.8936(3) 0.38478(11) 0.0317(4) Uani 1 1 d . . . . .
C9 C 0.22682(13) 0.8481(4) 0.44125(12) 0.0369(5) Uani 1 1 d . . . . .
H9 H 0.184256 0.943945 0.446722 0.044 Uiso 1 1 calc R U . . .
C10 C 0.25831(13) 0.6580(4) 0.48928(12) 0.0360(5) Uani 1 1 d . . . . .
H10 H 0.237176 0.625262 0.528910 0.043 Uiso 1 1 calc R U . . .
C11 C 0.34566(12) 0.5763(3) 0.42634(11) 0.0305(4) Uani 1 1 d . . . . .
C12 C 0.40991(12) 0.4198(4) 0.41909(11) 0.0330(4) Uani 1 1 d . . . . .
H12 H 0.425074 0.287675 0.452687 0.040 Uiso 1 1 calc R U . . .
C13 C 0.44864(12) 0.4471(3) 0.36958(11) 0.0310(4) Uani 1 1 d . . . . .
H13 H 0.433087 0.578785 0.335822 0.037 Uiso 1 1 calc R U . . .
C14 C 0.51348(12) 0.2920(3) 0.36224(11) 0.0296(4) Uani 1 1 d . . . . .
C15 C 0.53275(13) 0.0736(3) 0.39966(11) 0.0328(4) Uani 1 1 d . . . . .
H15 H 0.500808 0.018424 0.428467 0.039 Uiso 1 1 calc R U . . .
C16 C 0.59728(13) -0.0629(3) 0.39545(11) 0.0318(4) Uani 1 1 d . . . . .
H16 H 0.610319 -0.209493 0.421535 0.038 Uiso 1 1 calc R U . . .
C17 C 0.64251(12) 0.0191(3) 0.35228(10) 0.0294(4) Uani 1 1 d . . . . .
C18 C 0.62424(12) 0.2305(3) 0.31291(11) 0.0300(4) Uani 1 1 d . . . . .
H18 H 0.655505 0.282472 0.283085 0.036 Uiso 1 1 calc R U . . .
C19 C 0.55937(12) 0.3648(3) 0.31788(11) 0.0302(4) Uani 1 1 d . . . . .
H19 H 0.545863 0.509334 0.290574 0.036 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
C1 C2 1.374(4) . ?
C1 C6 1.374(3) . ?
C1 Br1 1.910(2) . ?
N1 C8 1.339(3) . ?
N1 C11 1.350(3) . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
Br2 C17 1.9092(19) . ?
N2 C10 1.331(3) . ?
N2 C11 1.341(3) . ?
C5 C6 1.384(3) . ?
C5 C4 1.390(3) . ?
C5 H5 0.9500 . ?
C4 C3 1.388(3) . ?
C4 C7 1.522(3) . ?
C3 H3 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.512(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.384(3) . ?
C9 C10 1.380(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.467(3) . ?
C12 C13 1.327(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.471(3) . ?
C13 H13 0.9500 . ?
C14 C19 1.397(3) . ?
C14 C15 1.404(3) . ?
C15 C16 1.383(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(3) . ?
C18 C19 1.386(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

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
C2 C1 C6 121.3(2) . . ?
C2 C1 Br1 119.80(17) . . ?
C6 C1 Br1 118.92(18) . . ?
C8 N1 C11 116.43(17) . . ?
C1 C2 C3 119.1(2) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C10 N2 C11 116.00(17) . . ?
C6 C5 C4 121.5(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C3 C4 C5 118.0(2) . . ?
C3 C4 C7 121.00(19) . . ?
C5 C4 C7 120.97(18) . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C1 C6 C5 119.0(2) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C8 C7 C4 112.46(17) . . ?
C8 C7 H7A 109.1 . . ?
C4 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C4 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
N1 C8 C9 121.50(19) . . ?
N1 C8 C7 117.29(18) . . ?
C9 C8 C7 121.18(19) . . ?
C10 C9 C8 117.40(19) . . ?
C10 C9 H9 121.3 . . ?
C8 C9 H9 121.3 . . ?
N2 C10 C9 122.64(19) . . ?
N2 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
N2 C11 N1 126.02(18) . . ?
N2 C11 C12 115.23(17) . . ?
N1 C11 C12 118.74(17) . . ?
C13 C12 C11 125.50(18) . . ?
C13 C12 H12 117.2 . . ?
C11 C12 H12 117.2 . . ?
C12 C13 C14 125.88(18) . . ?
C12 C13 H13 117.1 . . ?
C14 C13 H13 117.1 . . ?
C19 C14 C15 118.13(18) . . ?
C19 C14 C13 119.31(17) . . ?
C15 C14 C13 122.54(18) . . ?
C16 C15 C14 121.36(18) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 118.49(18) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
C18 C17 C16 122.00(18) . . ?
C18 C17 Br2 119.52(14) . . ?
C16 C17 Br2 118.48(15) . . ?
C17 C18 C19 118.65(18) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C18 C19 C14 121.33(18) . . ?
C18 C19 H19 119.3 . . ?
C14 C19 H19 119.3 . . ?

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
C6 C1 C2 C3 0.3(4) . . . . ?
Br1 C1 C2 C3 -179.65(18) . . . . ?
C6 C5 C4 C3 0.3(3) . . . . ?
C6 C5 C4 C7 -178.2(2) . . . . ?
C5 C4 C3 C2 -0.4(3) . . . . ?
C7 C4 C3 C2 178.1(2) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
Br1 C1 C6 C5 179.54(18) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C3 C4 C7 C8 131.6(2) . . . . ?
C5 C4 C7 C8 -49.9(3) . . . . ?
C11 N1 C8 C9 1.0(3) . . . . ?
C11 N1 C8 C7 -177.00(16) . . . . ?
C4 C7 C8 N1 91.2(2) . . . . ?
C4 C7 C8 C9 -86.8(2) . . . . ?
N1 C8 C9 C10 -0.3(3) . . . . ?
C7 C8 C9 C10 177.67(18) . . . . ?
C11 N2 C10 C9 1.2(3) . . . . ?
C8 C9 C10 N2 -0.9(3) . . . . ?
C10 N2 C11 N1 -0.4(3) . . . . ?
C10 N2 C11 C12 -179.51(17) . . . . ?
C8 N1 C11 N2 -0.7(3) . . . . ?
C8 N1 C11 C12 178.38(17) . . . . ?
N2 C11 C12 C13 -177.78(19) . . . . ?
N1 C11 C12 C13 3.0(3) . . . . ?
C11 C12 C13 C14 179.60(18) . . . . ?
C12 C13 C14 C19 -168.36(19) . . . . ?
C12 C13 C14 C15 10.2(3) . . . . ?
C19 C14 C15 C16 2.4(3) . . . . ?
C13 C14 C15 C16 -176.20(18) . . . . ?
C14 C15 C16 C17 -0.8(3) . . . . ?
C15 C16 C17 C18 -0.8(3) . . . . ?
C15 C16 C17 Br2 179.08(14) . . . . ?
C16 C17 C18 C19 0.9(3) . . . . ?
Br2 C17 C18 C19 -179.03(14) . . . . ?
C17 C18 C19 C14 0.8(3) . . . . ?
C15 C14 C19 C18 -2.3(3) . . . . ?
C13 C14 C19 C18 176.29(17) . . . . ?

_refine_diff_density_max         0.542
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.053

