# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_CSJ08_101_1_3_a
_database_code_depnum_ccdc_archive 'CCDC 2165867'
loop_
_audit_author_name
_audit_author_address
'wenlong Liu'
;Yangzhou University
China
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2022-10-21 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         'C27 H19 Br N2'
_chemical_formula_sum            'C27 H19 Br N2'
_chemical_formula_weight         451.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.7856(7)
_cell_length_b                   10.4391(7)
_cell_length_c                   11.5402(7)
_cell_angle_alpha                94.494(2)
_cell_angle_beta                 95.410(2)
_cell_angle_gamma                114.329(2)
_cell_volume                     1060.43(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7920
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      26.94

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.954
_shelx_estimated_absorpt_T_min   0.592
_shelx_estimated_absorpt_T_max   0.696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5116
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            16521
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.159
_diffrn_reflns_theta_max         27.517
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4840
_reflns_number_gt                3611
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0499P)²+0.3592P] 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         4840
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1055
_refine_ls_wR_factor_gt          0.0957
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.52725(4) 0.78059(3) 1.12479(2) 0.07208(14) Uani 1 1 d . . . . .
C1 C 0.4350(3) 0.7205(3) 0.96601(19) 0.0492(5) Uani 1 1 d . . . . .
C2 C 0.4493(3) 0.8188(3) 0.8906(2) 0.0567(6) Uani 1 1 d . . . . .
H2 H 0.497281 0.915141 0.917954 0.068 Uiso 1 1 calc R U . . .
C3 C 0.3920(3) 0.7735(2) 0.7737(2) 0.0512(6) Uani 1 1 d . . . . .
H3 H 0.400721 0.840455 0.722915 0.061 Uiso 1 1 calc R U . . .
C4 C 0.3213(2) 0.6301(2) 0.72954(18) 0.0383(4) Uani 1 1 d . . . . .
C5 C 0.2702(2) 0.5892(2) 0.60279(17) 0.0362(4) Uani 1 1 d . . . . .
C6 C 0.2371(2) 0.4641(2) 0.53330(17) 0.0345(4) Uani 1 1 d . . . . .
C7 C 0.1678(2) 0.3854(2) 0.31762(17) 0.0359(4) Uani 1 1 d . . . . .
C8 C 0.0236(3) 0.2800(2) 0.2911(2) 0.0490(5) Uani 1 1 d . . . . .
H8 H -0.049515 0.273824 0.339150 0.059 Uiso 1 1 calc R U . . .
C9 C -0.0116(3) 0.1825(3) 0.1911(2) 0.0638(7) Uani 1 1 d . . . . .
H9 H -0.109120 0.111103 0.171178 0.077 Uiso 1 1 calc R U . . .
C10 C 0.0974(4) 0.1920(3) 0.1224(2) 0.0628(7) Uani 1 1 d . . . . .
H10 H 0.073751 0.126652 0.055773 0.075 Uiso 1 1 calc R U . . .
C11 C 0.3628(3) 0.5783(3) 0.9263(2) 0.0587(6) Uani 1 1 d . . . . .
H11 H 0.351690 0.511952 0.978221 0.070 Uiso 1 1 calc R U . . .
C12 C 0.3068(3) 0.5342(2) 0.8086(2) 0.0547(6) Uani 1 1 d . . . . .
H12 H 0.258178 0.437641 0.782014 0.066 Uiso 1 1 calc R U . . .
C13 C 0.2417(3) 0.2970(3) 0.1507(2) 0.0629(7) Uani 1 1 d . . . . .
H13 H 0.315333 0.301927 0.103580 0.075 Uiso 1 1 calc R U . . .
C14 C 0.2781(3) 0.3955(3) 0.2490(2) 0.0497(5) Uani 1 1 d . . . . .
H14 H 0.375442 0.467297 0.268224 0.060 Uiso 1 1 calc R U . . .
C15 C 0.2177(2) 0.6244(2) 0.42513(18) 0.0366(4) Uani 1 1 d . . . . .
C16 C 0.1962(2) 0.6967(2) 0.32471(18) 0.0389(5) Uani 1 1 d . . . . .
C17 C 0.2611(3) 0.8446(2) 0.3427(2) 0.0452(5) Uani 1 1 d . . . . .
H17 H 0.316926 0.892368 0.414796 0.054 Uiso 1 1 calc R U . . .
C18 C 0.2433(3) 0.9203(3) 0.2547(2) 0.0588(6) Uani 1 1 d . . . . .
H18 H 0.286416 1.018865 0.267908 0.071 Uiso 1 1 calc R U . . .
C19 C 0.1625(4) 0.8515(3) 0.1480(3) 0.0705(8) Uani 1 1 d . . . . .
H19 H 0.152351 0.903148 0.088302 0.085 Uiso 1 1 calc R U . . .
C20 C 0.0966(4) 0.7067(3) 0.1292(2) 0.0712(8) Uani 1 1 d . . . . .
H20 H 0.040975 0.660133 0.056732 0.085 Uiso 1 1 calc R U . . .
C21 C 0.1119(3) 0.6286(3) 0.2174(2) 0.0558(6) Uani 1 1 d . . . . .
H21 H 0.065189 0.530121 0.204179 0.067 Uiso 1 1 calc R U . . .
C22 C 0.3614(2) 0.2985(2) 0.5338(2) 0.0450(5) Uani 1 1 d . . . . .
H22 H 0.442200 0.365292 0.503971 0.054 Uiso 1 1 calc R U . . .
C23 C 0.3639(3) 0.1712(2) 0.5549(2) 0.0541(6) Uani 1 1 d . . . . .
H23 H 0.446114 0.152911 0.539307 0.065 Uiso 1 1 calc R U . . .
C24 C 0.2459(3) 0.0717(2) 0.5986(2) 0.0513(6) Uani 1 1 d . . . . .
H24 H 0.247597 -0.014157 0.612689 0.062 Uiso 1 1 calc R U . . .
C25 C 0.1253(3) 0.0993(2) 0.6215(2) 0.0591(7) Uani 1 1 d . . . . .
H25 H 0.044802 0.031875 0.651231 0.071 Uiso 1 1 calc R U . . .
C26 C 0.1224(3) 0.2262(2) 0.6009(2) 0.0524(6) Uani 1 1 d . . . . .
H26 H 0.040029 0.243991 0.617049 0.063 Uiso 1 1 calc R U . . .
C27 C 0.2410(2) 0.3280(2) 0.55633(17) 0.0340(4) Uani 1 1 d . . . . .
N1 N 0.20417(18) 0.48816(16) 0.41985(14) 0.0352(4) Uani 1 1 d . . . . .
N2 N 0.25692(19) 0.68739(17) 0.53435(15) 0.0392(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.899(2) . ?
C1 C2 1.369(3) . ?
C1 C11 1.372(4) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(3) . ?
C3 H3 0.9300 . ?
C4 C12 1.380(3) . ?
C4 C5 1.470(3) . ?
C5 C6 1.375(3) . ?
C5 N2 1.382(3) . ?
C6 N1 1.386(3) . ?
C6 C27 1.481(3) . ?
C7 C8 1.372(3) . ?
C7 C14 1.373(3) . ?
C7 N1 1.441(2) . ?
C8 C9 1.393(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.364(4) . ?
C9 H9 0.9300 . ?
C10 C13 1.373(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.381(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 N2 1.319(3) . ?
C15 N1 1.369(2) . ?
C15 C16 1.476(3) . ?
C16 C21 1.381(3) . ?
C16 C17 1.395(3) . ?
C17 C18 1.376(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.366(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.366(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.387(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C27 1.377(3) . ?
C22 C23 1.379(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.367(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.369(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.375(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.386(3) . ?
C26 H26 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C11 120.6(2) . . ?
C2 C1 Br1 119.95(18) . . ?
C11 C1 Br1 119.33(18) . . ?
C1 C2 C3 119.3(2) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 121.8(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C12 C4 C3 117.2(2) . . ?
C12 C4 C5 123.73(19) . . ?
C3 C4 C5 119.05(19) . . ?
C6 C5 N2 109.90(17) . . ?
C6 C5 C4 130.33(18) . . ?
N2 C5 C4 119.69(17) . . ?
C5 C6 N1 105.33(16) . . ?
C5 C6 C27 133.80(18) . . ?
N1 C6 C27 120.72(17) . . ?
C8 C7 C14 121.6(2) . . ?
C8 C7 N1 119.18(18) . . ?
C14 C7 N1 119.23(19) . . ?
C7 C8 C9 118.9(2) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C10 C9 C8 119.8(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C13 120.7(2) . . ?
C9 C10 H10 119.7 . . ?
C13 C10 H10 119.7 . . ?
C1 C11 C12 119.5(2) . . ?
C1 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C4 C12 C11 121.5(2) . . ?
C4 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C10 C13 C14 120.2(2) . . ?
C10 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C7 C14 C13 118.8(2) . . ?
C7 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
N2 C15 N1 110.78(17) . . ?
N2 C15 C16 122.84(18) . . ?
N1 C15 C16 126.36(18) . . ?
C21 C16 C17 118.4(2) . . ?
C21 C16 C15 124.8(2) . . ?
C17 C16 C15 116.82(19) . . ?
C18 C17 C16 120.6(2) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 120.3(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 119.9(2) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C21 120.5(3) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C16 C21 C20 120.2(2) . . ?
C16 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C27 C22 C23 120.9(2) . . ?
C27 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C24 C23 C22 120.3(2) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 119.6(2) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C24 C25 C26 120.4(2) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C27 120.7(2) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C22 C27 C26 118.12(19) . . ?
C22 C27 C6 121.24(17) . . ?
C26 C27 C6 120.64(18) . . ?
C15 N1 C6 107.58(16) . . ?
C15 N1 C7 128.35(17) . . ?
C6 N1 C7 124.04(16) . . ?
C15 N2 C5 106.40(16) . . ?

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
C11 C1 C2 C3 -0.8(4) . . . . ?
Br1 C1 C2 C3 175.01(19) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C3 C4 C12 1.8(4) . . . . ?
C2 C3 C4 C5 -176.6(2) . . . . ?
C12 C4 C5 C6 -18.3(4) . . . . ?
C3 C4 C5 C6 160.0(2) . . . . ?
C12 C4 C5 N2 165.2(2) . . . . ?
C3 C4 C5 N2 -16.4(3) . . . . ?
N2 C5 C6 N1 0.5(2) . . . . ?
C4 C5 C6 N1 -176.2(2) . . . . ?
N2 C5 C6 C27 175.9(2) . . . . ?
C4 C5 C6 C27 -0.8(4) . . . . ?
C14 C7 C8 C9 -0.9(3) . . . . ?
N1 C7 C8 C9 178.9(2) . . . . ?
C7 C8 C9 C10 0.9(4) . . . . ?
C8 C9 C10 C13 -0.1(4) . . . . ?
C2 C1 C11 C12 1.3(4) . . . . ?
Br1 C1 C11 C12 -174.5(2) . . . . ?
C3 C4 C12 C11 -1.3(4) . . . . ?
C5 C4 C12 C11 177.0(2) . . . . ?
C1 C11 C12 C4 -0.2(4) . . . . ?
C9 C10 C13 C14 -0.5(4) . . . . ?
C8 C7 C14 C13 0.3(3) . . . . ?
N1 C7 C14 C13 -179.6(2) . . . . ?
C10 C13 C14 C7 0.5(4) . . . . ?
N2 C15 C16 C21 -158.5(2) . . . . ?
N1 C15 C16 C21 23.1(3) . . . . ?
N2 C15 C16 C17 18.6(3) . . . . ?
N1 C15 C16 C17 -159.9(2) . . . . ?
C21 C16 C17 C18 -1.1(3) . . . . ?
C15 C16 C17 C18 -178.3(2) . . . . ?
C16 C17 C18 C19 -0.5(4) . . . . ?
C17 C18 C19 C20 1.3(4) . . . . ?
C18 C19 C20 C21 -0.5(5) . . . . ?
C17 C16 C21 C20 1.8(4) . . . . ?
C15 C16 C21 C20 178.8(2) . . . . ?
C19 C20 C21 C16 -1.1(4) . . . . ?
C27 C22 C23 C24 0.1(4) . . . . ?
C22 C23 C24 C25 -0.1(4) . . . . ?
C23 C24 C25 C26 0.0(4) . . . . ?
C24 C25 C26 C27 0.2(4) . . . . ?
C23 C22 C27 C26 0.1(3) . . . . ?
C23 C22 C27 C6 -179.7(2) . . . . ?
C25 C26 C27 C22 -0.2(4) . . . . ?
C25 C26 C27 C6 179.5(2) . . . . ?
C5 C6 C27 C22 -98.7(3) . . . . ?
N1 C6 C27 C22 76.1(3) . . . . ?
C5 C6 C27 C26 81.5(3) . . . . ?
N1 C6 C27 C26 -103.6(2) . . . . ?
N2 C15 N1 C6 0.0(2) . . . . ?
C16 C15 N1 C6 178.59(19) . . . . ?
N2 C15 N1 C7 -178.10(18) . . . . ?
C16 C15 N1 C7 0.5(3) . . . . ?
C5 C6 N1 C15 -0.3(2) . . . . ?
C27 C6 N1 C15 -176.43(17) . . . . ?
C5 C6 N1 C7 177.91(17) . . . . ?
C27 C6 N1 C7 1.8(3) . . . . ?
C8 C7 N1 C15 -101.8(2) . . . . ?
C14 C7 N1 C15 78.0(3) . . . . ?
C8 C7 N1 C6 80.3(3) . . . . ?
C14 C7 N1 C6 -99.8(2) . . . . ?
N1 C15 N2 C5 0.3(2) . . . . ?
C16 C15 N2 C5 -178.36(18) . . . . ?
C6 C5 N2 C15 -0.5(2) . . . . ?
C4 C5 N2 C15 176.62(18) . . . . ?

_refine_diff_density_max         0.589
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.047

