# 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_cu_chengdu1119_ZWG_DCM_0m
_database_code_depnum_ccdc_archive 'CCDC 2072332'
loop_
_audit_author_name
_audit_author_address
'Miao Fang'
;UESTC
China
;
_audit_update_record             
;
2021-03-23 deposited with the CCDC.	2021-07-14 downloaded from the CCDC.
;
_audit_creation_method           
;
FinalCif by Daniel Kratzert, Freiburg 2019,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C20 H13 Br N4'
_chemical_formula_moiety         ?
_chemical_formula_weight         389.25
_chemical_melting_point          ?
_chemical_absolute_configuration ?
_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                   11.4145(5)
_cell_length_b                   17.9367(8)
_cell_length_c                   8.0609(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.893(2)
_cell_angle_gamma                90
_cell_volume                     1561.46(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7884
_cell_measurement_theta_min      4.0935
_cell_measurement_theta_max      68.2795
_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    3.663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4984
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.528
_shelx_estimated_absorpt_T_max   0.930
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      173(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'Microfocus sealed tube'
_diffrn_source_type              ?
_diffrn_source_voltage           50.0
_diffrn_source_current           1.2
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Ius Duo PHOTON II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            11658
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_theta_min         4.093
_diffrn_reflns_theta_max         68.274
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2837
_reflns_number_gt                2700
_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 BIS V6.2.12/2019-08-12'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT (G. Sheldrick)'
_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)+(0.0456P)²+0.8086P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2837
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0273
_refine_ls_wR_factor_ref         0.0780
_refine_ls_wR_factor_gt          0.0771
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'

_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_
_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 -0.02519(2) 0.66258(2) 0.65290(3) 0.03185(11) Uani 1 1 d . . . . .
N1 N 0.31721(14) 0.50479(9) 0.3273(2) 0.0246(3) Uani 1 1 d . . . . .
N2 N 0.26792(13) 0.44300(8) 0.6090(2) 0.0218(3) Uani 1 1 d . . . . .
N3 N 0.10889(14) 0.51262(9) 0.7667(2) 0.0250(3) Uani 1 1 d . . . . .
C1 C 0.45796(16) 0.40415(10) 0.3370(2) 0.0235(4) Uani 1 1 d . . . . .
C2 C 0.5090(2) 0.33567(10) 0.4045(3) 0.0303(4) Uani 1 1 d . . . . .
H2 H 0.485695 0.312758 0.495366 0.036 Uiso 1 1 calc R U . . .
C3 C 0.5935(2) 0.30081(12) 0.3404(3) 0.0364(5) Uani 1 1 d . . . . .
H3 H 0.627977 0.254157 0.387420 0.044 Uiso 1 1 calc R U . . .
C4 C 0.62812(19) 0.33373(11) 0.2073(3) 0.0315(5) Uani 1 1 d . . . . .
H4 H 0.686040 0.309699 0.163092 0.038 Uiso 1 1 calc R U . . .
C5 C 0.57787(19) 0.40151(12) 0.1399(3) 0.0339(5) Uani 1 1 d . . . . .
H5 H 0.601585 0.424279 0.049223 0.041 Uiso 1 1 calc R U . . .
C6 C 0.49298(18) 0.43665(12) 0.2035(3) 0.0304(4) Uani 1 1 d . . . . .
H6 H 0.458506 0.483210 0.155693 0.037 Uiso 1 1 calc R U . . .
C7 C 0.36774(16) 0.44276(10) 0.4044(2) 0.0227(4) Uani 1 1 d . . . . .
C8 C 0.23555(16) 0.53943(10) 0.3958(2) 0.0230(4) Uani 1 1 d . . . . .
C9 C 0.21114(16) 0.50843(10) 0.5436(2) 0.0223(4) Uani 1 1 d . . . . .
C11 C 0.17650(17) 0.60568(10) 0.3238(3) 0.0259(4) Uani 1 1 d . . . . .
C12 C 0.09916(17) 0.63979(10) 0.4047(3) 0.0263(4) Uani 1 1 d . . . . .
H12 H 0.059556 0.685236 0.357432 0.032 Uiso 1 1 calc R U . . .
C13 C 0.07800(16) 0.61038(10) 0.5497(3) 0.0255(4) Uani 1 1 d . . . . .
C14 C 0.13109(16) 0.54248(10) 0.6265(2) 0.0232(4) Uani 1 1 d . . . . .
C15 C 0.1989(2) 0.63890(12) 0.1650(3) 0.0328(4) Uani 1 1 d . . . . .
H15A H 0.165043 0.605661 0.064309 0.049 Uiso 1 1 calc R U . . .
H15B H 0.288063 0.645065 0.188262 0.049 Uiso 1 1 calc R U . . .
H15C H 0.158028 0.687590 0.139142 0.049 Uiso 1 1 calc R U . . .
C16 C 0.24403(16) 0.40903(10) 0.7496(2) 0.0231(4) Uani 1 1 d . . . . .
C17 C 0.16336(16) 0.44662(10) 0.8246(2) 0.0237(4) Uani 1 1 d . . . . .
C18 C 0.29554(19) 0.33889(10) 0.8118(3) 0.0258(4) Uani 1 1 d . . . . .
H18 H 0.349803 0.314831 0.760915 0.031 Uiso 1 1 calc R U . . .
C19 C 0.26647(18) 0.30611(11) 0.9458(3) 0.0296(4) Uani 1 1 d . . . . .
H19 H 0.299281 0.258391 0.986975 0.036 Uiso 1 1 calc R U . . .
C20 C 0.1875(2) 0.34274(11) 1.0244(3) 0.0301(4) Uani 1 1 d . . . . .
H20 H 0.168076 0.319185 1.117792 0.036 Uiso 1 1 calc R U . . .
C21 C 0.13914(18) 0.41102(11) 0.9679(3) 0.0281(4) Uani 1 1 d . . . . .
H21 H 0.088633 0.435241 1.024780 0.034 Uiso 1 1 calc R U . . .
N4 N 0.34796(14) 0.40777(8) 0.5429(2) 0.0247(3) Uani 1 1 d . . . . .


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 C13 1.8951(19) . ?
N1 C7 1.313(2) . ?
N1 C8 1.376(2) . ?
N2 N4 1.354(2) . ?
N2 C9 1.362(2) . ?
N2 C16 1.389(2) . ?
N3 C14 1.346(3) . ?
N3 C17 1.348(3) . ?
C1 C6 1.391(3) . ?
C1 C2 1.393(3) . ?
C1 C7 1.483(3) . ?
C2 C3 1.382(3) . ?
C3 C4 1.389(3) . ?
C4 C5 1.379(3) . ?
C5 C6 1.386(3) . ?
C7 N4 1.362(2) . ?
C8 C11 1.396(3) . ?
C8 C9 1.422(3) . ?
C9 C14 1.432(3) . ?
C11 C12 1.397(3) . ?
C11 C15 1.507(3) . ?
C12 C13 1.373(3) . ?
C13 C14 1.411(3) . ?
C16 C18 1.410(3) . ?
C16 C17 1.424(3) . ?
C17 C21 1.423(3) . ?
C18 C19 1.362(3) . ?
C19 C20 1.420(3) . ?
C20 C21 1.360(3) . ?

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
C7 N1 C8 116.31(16) . . ?
N4 N2 C9 123.18(16) . . ?
N4 N2 C16 116.86(15) . . ?
C9 N2 C16 119.96(15) . . ?
C14 N3 C17 116.66(16) . . ?
C6 C1 C2 118.89(18) . . ?
C6 C1 C7 119.70(17) . . ?
C2 C1 C7 121.41(18) . . ?
C3 C2 C1 120.5(2) . . ?
C2 C3 C4 120.26(19) . . ?
C5 C4 C3 119.54(19) . . ?
C4 C5 C6 120.5(2) . . ?
C5 C6 C1 120.38(19) . . ?
N1 C7 N4 127.93(17) . . ?
N1 C7 C1 118.21(17) . . ?
N4 C7 C1 113.86(16) . . ?
N1 C8 C11 121.08(17) . . ?
N1 C8 C9 120.12(16) . . ?
C11 C8 C9 118.79(17) . . ?
N2 C9 C8 117.62(16) . . ?
N2 C9 C14 118.86(17) . . ?
C8 C9 C14 123.52(17) . . ?
C8 C11 C12 118.16(18) . . ?
C8 C11 C15 119.85(17) . . ?
C12 C11 C15 121.99(17) . . ?
C13 C12 C11 122.74(17) . . ?
C12 C13 C14 122.45(17) . . ?
C12 C13 Br1 119.31(14) . . ?
C14 C13 Br1 118.23(14) . . ?
N3 C14 C13 122.76(17) . . ?
N3 C14 C9 122.95(17) . . ?
C13 C14 C9 114.29(17) . . ?
N2 C16 C18 120.81(17) . . ?
N2 C16 C17 117.59(16) . . ?
C18 C16 C17 121.58(18) . . ?
N3 C17 C21 119.07(17) . . ?
N3 C17 C16 123.90(17) . . ?
C21 C17 C16 117.03(17) . . ?
C19 C18 C16 119.12(18) . . ?
C18 C19 C20 120.47(18) . . ?
C21 C20 C19 120.99(19) . . ?
C20 C21 C17 120.76(18) . . ?
N2 N4 C7 114.81(15) . . ?

