# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_las0603_3_0m
_database_code_depnum_ccdc_archive 'CCDC 2082252'
loop_
_audit_author_name
_audit_author_address
'Zhiyong Ma'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2021-05-07 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_audit_creation_date             2019-06-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H11 Br N2'
_chemical_formula_sum            'C19 H11 Br N2'
_chemical_formula_weight         347.21
_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 0.0033 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'
Br Br -0.2901 2.4595 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.0288(4)
_cell_length_b                   10.1219(10)
_cell_length_c                   18.2137(17)
_cell_angle_alpha                87.368(4)
_cell_angle_beta                 83.942(4)
_cell_angle_gamma                85.116(4)
_cell_volume                     735.40(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8914
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.323
_cell_measurement_theta_min      2.969
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    2.792
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15060
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         27.530
_diffrn_reflns_theta_min         2.969
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2766
_reflns_number_total             3303
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         1.133
_refine_diff_density_min         -0.699
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3303
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.076
_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)+(0.0891P)²+0.2084P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1358
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C004(H004), C005(H005), C009(H009), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Br01 Br 0.14300(8) 1.07448(3) 0.37296(2) 0.05594(16) Uani 1 1 d . . . . .
N002 N 0.8025(6) 0.6718(2) 0.23607(11) 0.0412(5) Uani 1 1 d . . . . .
C003 C 0.6294(8) 0.7187(3) 0.43696(13) 0.0397(6) Uani 1 1 d . . . . .
C004 C 0.4440(8) 0.8415(3) 0.43918(14) 0.0424(6) Uani 1 1 d . . . . .
H004 H 0.3650 0.8793 0.4839 0.051 Uiso 1 1 calc R . . . .
C005 C 0.7521(7) 0.6616(3) 0.37014(13) 0.0389(6) Uani 1 1 d . . . . .
H005 H 0.8791 0.5805 0.3696 0.047 Uiso 1 1 calc R . . . .
C006 C 0.6815(7) 0.7281(3) 0.30429(13) 0.0372(6) Uani 1 1 d . . . . .
C007 C 0.3820(7) 0.9048(3) 0.37299(15) 0.0391(6) Uani 1 1 d . . . . .
C008 C 0.8107(7) 0.5372(3) 0.22091(13) 0.0407(6) Uani 1 1 d . . . . .
C009 C 0.4936(7) 0.8502(3) 0.30563(14) 0.0404(6) Uani 1 1 d . . . . .
H009 H 0.4437 0.8945 0.2618 0.048 Uiso 1 1 calc R . . . .
C00A C 0.9803(8) 0.5170(3) 0.15007(15) 0.0454(6) Uani 1 1 d . . . . .
C00B C 0.7037(9) 0.6511(3) 0.50657(15) 0.0480(7) Uani 1 1 d . . . . .
N00C N 0.7596(9) 0.6018(3) 0.55975(15) 0.0664(8) Uani 1 1 d . . . . .
C00D C 1.0737(7) 0.6443(3) 0.12118(14) 0.0443(6) Uani 1 1 d . . . . .
C00E C 0.9579(7) 0.7390(3) 0.17383(13) 0.0406(6) Uani 1 1 d . . . . .
C00F C 0.6712(9) 0.4337(3) 0.26297(16) 0.0491(7) Uani 1 1 d . . . . .
H00F H 0.5588 0.4473 0.3096 0.059 Uiso 1 1 calc R . . . .
C00G C 1.0072(9) 0.8724(3) 0.16161(16) 0.0504(7) Uani 1 1 d . . . . .
H00G H 0.9319 0.9342 0.1971 0.061 Uiso 1 1 calc R . . . .
C00H C 1.0145(10) 0.3908(4) 0.12158(18) 0.0594(9) Uani 1 1 d . . . . .
H00H H 1.1261 0.3759 0.0750 0.071 Uiso 1 1 calc R . . . .
C00I C 0.7062(10) 0.3099(3) 0.2327(2) 0.0588(8) Uani 1 1 d . . . . .
H00I H 0.6110 0.2394 0.2592 0.071 Uiso 1 1 calc R . . . .
C00J C 1.1740(10) 0.9100(4) 0.0941(2) 0.0636(9) Uani 1 1 d . . . . .
H00J H 1.2080 0.9990 0.0841 0.076 Uiso 1 1 calc R . . . .
C00K C 1.2445(9) 0.6853(4) 0.05435(17) 0.0593(9) Uani 1 1 d . . . . .
H00K H 1.3257 0.6237 0.0192 0.071 Uiso 1 1 calc R . . . .
C00L C 1.2914(10) 0.8177(4) 0.04106(19) 0.0676(10) Uani 1 1 d . . . . .
H00L H 1.4023 0.8457 -0.0036 0.081 Uiso 1 1 calc R . . . .
C00M C 0.8795(11) 0.2880(4) 0.1639(2) 0.0682(10) Uani 1 1 d . . . . .
H00M H 0.9052 0.2027 0.1460 0.082 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
Br01 C007 1.896(3) . ?
N002 C006 1.413(3) . ?
N002 C008 1.399(4) . ?
N002 C00E 1.411(3) . ?
C003 C004 1.395(4) . ?
C003 C005 1.396(3) . ?
C003 C00B 1.459(4) . ?
C004 H004 0.9300 . ?
C004 C007 1.375(4) . ?
C005 H005 0.9300 . ?
C005 C006 1.392(4) . ?
C006 C009 1.393(4) . ?
C007 C009 1.384(4) . ?
C008 C00A 1.410(3) . ?
C008 C00F 1.391(4) . ?
C009 H009 0.9300 . ?
C00A C00D 1.434(4) . ?
C00A C00H 1.392(5) . ?
C00B N00C 1.105(4) . ?
C00D C00E 1.404(4) . ?
C00D C00K 1.398(4) . ?
C00E C00G 1.386(4) . ?
C00F H00F 0.9300 . ?
C00F C00I 1.382(5) . ?
C00G H00G 0.9300 . ?
C00G C00J 1.391(4) . ?
C00H H00H 0.9300 . ?
C00H C00M 1.381(6) . ?
C00I H00I 0.9300 . ?
C00I C00M 1.386(5) . ?
C00J H00J 0.9300 . ?
C00J C00L 1.393(6) . ?
C00K H00K 0.9300 . ?
C00K C00L 1.376(6) . ?
C00L H00L 0.9300 . ?
C00M H00M 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
C008 N002 C006 125.4(2) . . ?
C008 N002 C00E 108.4(2) . . ?
C00E N002 C006 126.1(2) . . ?
C004 C003 C005 121.6(2) . . ?
C004 C003 C00B 118.6(2) . . ?
C005 C003 C00B 119.8(3) . . ?
C003 C004 H004 121.1 . . ?
C007 C004 C003 117.8(2) . . ?
C007 C004 H004 121.1 . . ?
C003 C005 H005 120.5 . . ?
C006 C005 C003 119.0(3) . . ?
C006 C005 H005 120.5 . . ?
C005 C006 N002 119.8(2) . . ?
C005 C006 C009 120.1(2) . . ?
C009 C006 N002 120.1(2) . . ?
C004 C007 Br01 119.4(2) . . ?
C004 C007 C009 122.3(3) . . ?
C009 C007 Br01 118.3(2) . . ?
N002 C008 C00A 108.8(2) . . ?
C00F C008 N002 129.7(2) . . ?
C00F C008 C00A 121.5(3) . . ?
C006 C009 H009 120.4 . . ?
C007 C009 C006 119.2(2) . . ?
C007 C009 H009 120.4 . . ?
C008 C00A C00D 106.7(3) . . ?
C00H C00A C008 119.7(3) . . ?
C00H C00A C00D 133.5(3) . . ?
N00C C00B C003 178.9(3) . . ?
C00E C00D C00A 108.3(2) . . ?
C00K C00D C00A 132.6(3) . . ?
C00K C00D C00E 119.2(3) . . ?
C00D C00E N002 107.8(2) . . ?
C00G C00E N002 130.2(3) . . ?
C00G C00E C00D 122.0(2) . . ?
C008 C00F H00F 121.3 . . ?
C00I C00F C008 117.4(3) . . ?
C00I C00F H00F 121.3 . . ?
C00E C00G H00G 121.4 . . ?
C00E C00G C00J 117.3(3) . . ?
C00J C00G H00G 121.4 . . ?
C00A C00H H00H 120.7 . . ?
C00M C00H C00A 118.7(3) . . ?
C00M C00H H00H 120.7 . . ?
C00F C00I H00I 119.1 . . ?
C00F C00I C00M 121.7(3) . . ?
C00M C00I H00I 119.1 . . ?
C00G C00J H00J 119.2 . . ?
C00G C00J C00L 121.7(3) . . ?
C00L C00J H00J 119.2 . . ?
C00D C00K H00K 120.3 . . ?
C00L C00K C00D 119.5(3) . . ?
C00L C00K H00K 120.3 . . ?
C00J C00L H00L 119.8 . . ?
C00K C00L C00J 120.4(3) . . ?
C00K C00L H00L 119.8 . . ?
C00H C00M C00I 121.0(3) . . ?
C00H C00M H00M 119.5 . . ?
C00I C00M H00M 119.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
