# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_Compound_1b
_database_code_depnum_ccdc_archive 'CCDC 1960596'
loop_
_audit_author_name
_audit_author_address
'Ruben A Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2019-10-21 deposited with the CCDC.	2020-01-28 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         'C20 H15 Br N2 O2'
_chemical_formula_sum            'C20 H15 Br N2 O2'
_chemical_formula_weight         395.25

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'
O O 0.0106 0.0060 '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      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                   5.586(3)
_cell_length_b                   26.400(12)
_cell_length_c                   11.913(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.885(10)
_cell_angle_gamma                90
_cell_volume                     1744.2(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9975
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      25.76

_exptl_crystal_description       platy
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.423
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.156
_exptl_absorpt_coefficient_mu    2.372
_shelx_estimated_absorpt_T_min   0.434
_shelx_estimated_absorpt_T_max   0.709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3701
_exptl_absorpt_correction_T_max  0.7085
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker Smart Apex CCD diffractometer 01-670-03'
_diffrn_measurement_method       ω-scans
_diffrn_reflns_number            65456
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_av_R_equivalents  0.0846
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.312
_diffrn_reflns_theta_max         30.076
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5095
_reflns_number_gt                2781
_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       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_cell_refinement       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLe (Hübschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.0420P)²+1.6515P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5095
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1286
_refine_ls_wR_factor_gt          0.1070
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_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 -0.35950(8) -0.03097(2) 0.37472(4) 0.06981(17) Uani 1 1 d . . . . .
O1 O 0.6797(4) 0.22293(9) 0.6183(2) 0.0622(7) Uani 1 1 d . . . . .
O2 O 0.5979(4) 0.14119(8) 0.59161(19) 0.0519(6) Uani 1 1 d . . . . .
C1 C 0.5495(5) 0.18969(11) 0.5737(3) 0.0414(7) Uani 1 1 d . . . . .
C2 C 0.3297(5) 0.20005(10) 0.4957(3) 0.0404(7) Uani 1 1 d . . . . .
C3 C 0.1926(6) 0.16133(11) 0.4489(3) 0.0427(7) Uani 1 1 d . . . . .
H3 H 0.247449 0.129079 0.470202 0.051 Uiso 1 1 calc R U . . .
N4 N -0.3342(5) 0.18763(10) 0.2464(2) 0.0498(7) Uani 1 1 d . . . . .
H4 H -0.422(6) 0.2069(14) 0.200(3) 0.060 Uiso 1 1 d . U . . .
C5 C -0.1290(6) 0.20290(11) 0.3092(3) 0.0464(8) Uani 1 1 d . . . . .
H5 H -0.067308 0.235641 0.310311 0.056 Uiso 1 1 calc R U . . .
C7 C -0.0243(5) 0.16280(10) 0.3716(2) 0.0409(7) Uani 1 1 d . . . . .
C8 C -0.1751(6) 0.06915(11) 0.3759(3) 0.0433(7) Uani 1 1 d . . . . .
H8 H -0.050311 0.056740 0.427184 0.052 Uiso 1 1 calc R U . . .
C9 C -0.3587(6) 0.03823(11) 0.3308(3) 0.0475(8) Uani 1 1 d . . . . .
C10 C -0.5495(6) 0.05520(13) 0.2539(3) 0.0547(9) Uani 1 1 d . . . . .
H10 H -0.670860 0.032875 0.225673 0.066 Uiso 1 1 calc R U . . .
C11 C -0.5581(6) 0.10491(13) 0.2198(3) 0.0535(8) Uani 1 1 d . . . . .
H11 H -0.683283 0.116896 0.168110 0.064 Uiso 1 1 calc R U . . .
C12 C -0.3733(6) 0.13664(11) 0.2652(3) 0.0422(7) Uani 1 1 d . . . . .
C13 C -0.1808(5) 0.11962(10) 0.3426(2) 0.0375(6) Uani 1 1 d . . . . .
N14 N 0.0788(5) 0.27664(10) 0.5169(2) 0.0469(6) Uani 1 1 d . . . . .
H14 H -0.026(6) 0.2615(13) 0.557(3) 0.056 Uiso 1 1 d . U . . .
C15 C 0.2715(5) 0.25414(11) 0.4750(3) 0.0427(7) Uani 1 1 d . . . . .
C16 C 0.3857(6) 0.28943(11) 0.4188(3) 0.0487(8) Uani 1 1 d . . . . .
H16 H 0.522251 0.284043 0.382712 0.058 Uiso 1 1 calc R U . . .
C17 C 0.2963(6) 0.38580(13) 0.3857(3) 0.0581(9) Uani 1 1 d . . . . .
H17 H 0.423697 0.392890 0.344629 0.070 Uiso 1 1 calc R U . . .
C18 C 0.1416(7) 0.42318(13) 0.4095(3) 0.0619(10) Uani 1 1 d . . . . .
H18 H 0.164430 0.455959 0.384229 0.074 Uiso 1 1 calc R U . . .
C19 C -0.0484(7) 0.41322(13) 0.4704(3) 0.0598(9) Uani 1 1 d . . . . .
H19 H -0.150445 0.439507 0.485757 0.072 Uiso 1 1 calc R U . . .
C20 C -0.0899(6) 0.36555(13) 0.5087(3) 0.0534(8) Uani 1 1 d . . . . .
H20 H -0.219711 0.358985 0.548597 0.064 Uiso 1 1 calc R U . . .
C21 C 0.0676(5) 0.32729(11) 0.4861(3) 0.0413(7) Uani 1 1 d . . . . .
C22 C 0.2605(5) 0.33660(11) 0.4242(3) 0.0440(7) Uani 1 1 d . . . . .
C23 C 0.8114(6) 0.12961(13) 0.6681(3) 0.0568(9) Uani 1 1 d . . . . .
H23A H 0.833537 0.093566 0.672131 0.085 Uiso 1 1 calc R U . . .
H23B H 0.793328 0.142533 0.741921 0.085 Uiso 1 1 calc R U . . .
H23C H 0.949184 0.145026 0.641037 0.085 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 C9 1.901(3) . ?
O1 C1 1.220(3) . ?
O2 C1 1.321(3) . ?
O2 C23 1.444(4) . ?
C1 C2 1.475(4) . ?
C2 C3 1.356(4) . ?
C2 C15 1.478(4) . ?
C3 C7 1.432(4) . ?
C3 H3 0.9300 . ?
N4 C5 1.353(4) . ?
N4 C12 1.386(4) . ?
N4 H4 0.86(4) . ?
C5 C7 1.382(4) . ?
C5 H5 0.9300 . ?
C7 C13 1.453(4) . ?
C8 C9 1.369(4) . ?
C8 C13 1.389(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.394(5) . ?
C10 C11 1.373(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.404(4) . ?
N14 C15 1.375(4) . ?
N14 C21 1.386(4) . ?
N14 H14 0.89(4) . ?
C15 C16 1.351(4) . ?
C16 C22 1.433(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.364(5) . ?
C17 C22 1.400(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.381(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.387(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.398(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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 O2 C23 116.4(2) . . ?
O1 C1 O2 121.8(3) . . ?
O1 C1 C2 123.3(3) . . ?
O2 C1 C2 114.9(2) . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 C15 123.9(3) . . ?
C1 C2 C15 115.7(2) . . ?
C2 C3 C7 129.5(3) . . ?
C2 C3 H3 115.2 . . ?
C7 C3 H3 115.2 . . ?
C5 N4 C12 109.8(3) . . ?
C5 N4 H4 124(2) . . ?
C12 N4 H4 126(2) . . ?
N4 C5 C7 110.2(3) . . ?
N4 C5 H5 124.9 . . ?
C7 C5 H5 124.9 . . ?
C5 C7 C3 129.6(3) . . ?
C5 C7 C13 105.6(3) . . ?
C3 C7 C13 124.8(3) . . ?
C9 C8 C13 118.0(3) . . ?
C9 C8 H8 121.0 . . ?
C13 C8 H8 121.0 . . ?
C8 C9 C10 123.0(3) . . ?
C8 C9 Br1 119.4(2) . . ?
C10 C9 Br1 117.6(2) . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 117.6(3) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 H11 121.2 . . ?
N4 C12 C11 130.3(3) . . ?
N4 C12 C13 107.1(3) . . ?
C11 C12 C13 122.6(3) . . ?
C8 C13 C12 118.9(3) . . ?
C8 C13 C7 133.8(3) . . ?
C12 C13 C7 107.3(2) . . ?
C15 N14 C21 109.4(3) . . ?
C15 N14 H14 126(2) . . ?
C21 N14 H14 124(2) . . ?
C16 C15 N14 108.6(3) . . ?
C16 C15 C2 129.9(3) . . ?
N14 C15 C2 121.5(3) . . ?
C15 C16 C22 108.3(3) . . ?
C15 C16 H16 125.8 . . ?
C22 C16 H16 125.8 . . ?
C18 C17 C22 119.0(3) . . ?
C18 C17 H17 120.5 . . ?
C22 C17 H17 120.5 . . ?
C17 C18 C19 121.2(3) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C20 C19 C18 121.5(3) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C21 117.9(3) . . ?
C19 C20 H20 121.0 . . ?
C21 C20 H20 121.0 . . ?
N14 C21 C20 131.3(3) . . ?
N14 C21 C22 107.2(3) . . ?
C20 C21 C22 121.4(3) . . ?
C21 C22 C17 119.0(3) . . ?
C21 C22 C16 106.4(3) . . ?
C17 C22 C16 134.6(3) . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
C23 O2 C1 O1 0.9(5) . . . . ?
C23 O2 C1 C2 -179.7(3) . . . . ?
O1 C1 C2 C3 -180.0(3) . . . . ?
O2 C1 C2 C3 0.6(4) . . . . ?
O1 C1 C2 C15 -0.9(5) . . . . ?
O2 C1 C2 C15 179.7(3) . . . . ?
C1 C2 C3 C7 -179.6(3) . . . . ?
C15 C2 C3 C7 1.4(6) . . . . ?
C12 N4 C5 C7 0.2(4) . . . . ?
N4 C5 C7 C3 179.9(3) . . . . ?
N4 C5 C7 C13 0.4(4) . . . . ?
C2 C3 C7 C5 12.4(6) . . . . ?
C2 C3 C7 C13 -168.2(3) . . . . ?
C13 C8 C9 C10 -0.2(5) . . . . ?
C13 C8 C9 Br1 -179.5(2) . . . . ?
C8 C9 C10 C11 0.3(6) . . . . ?
Br1 C9 C10 C11 179.7(3) . . . . ?
C9 C10 C11 C12 -0.5(5) . . . . ?
C5 N4 C12 C11 -179.8(3) . . . . ?
C5 N4 C12 C13 -0.7(4) . . . . ?
C10 C11 C12 N4 179.6(3) . . . . ?
C10 C11 C12 C13 0.6(5) . . . . ?
C9 C8 C13 C12 0.2(5) . . . . ?
C9 C8 C13 C7 179.5(3) . . . . ?
N4 C12 C13 C8 -179.6(3) . . . . ?
C11 C12 C13 C8 -0.5(5) . . . . ?
N4 C12 C13 C7 0.9(3) . . . . ?
C11 C12 C13 C7 -179.9(3) . . . . ?
C5 C7 C13 C8 179.9(3) . . . . ?
C3 C7 C13 C8 0.3(6) . . . . ?
C5 C7 C13 C12 -0.8(3) . . . . ?
C3 C7 C13 C12 179.7(3) . . . . ?
C21 N14 C15 C16 0.6(4) . . . . ?
C21 N14 C15 C2 179.4(3) . . . . ?
C3 C2 C15 C16 -111.7(4) . . . . ?
C1 C2 C15 C16 69.3(5) . . . . ?
C3 C2 C15 N14 69.7(4) . . . . ?
C1 C2 C15 N14 -109.2(3) . . . . ?
N14 C15 C16 C22 -0.3(4) . . . . ?
C2 C15 C16 C22 -179.0(3) . . . . ?
C22 C17 C18 C19 0.0(6) . . . . ?
C17 C18 C19 C20 -0.4(6) . . . . ?
C18 C19 C20 C21 1.0(5) . . . . ?
C15 N14 C21 C20 -179.1(3) . . . . ?
C15 N14 C21 C22 -0.6(3) . . . . ?
C19 C20 C21 N14 177.1(3) . . . . ?
C19 C20 C21 C22 -1.3(5) . . . . ?
N14 C21 C22 C17 -177.8(3) . . . . ?
C20 C21 C22 C17 0.9(5) . . . . ?
N14 C21 C22 C16 0.4(3) . . . . ?
C20 C21 C22 C16 179.1(3) . . . . ?
C18 C17 C22 C21 -0.2(5) . . . . ?
C18 C17 C22 C16 -177.8(4) . . . . ?
C15 C16 C22 C21 0.0(4) . . . . ?
C15 C16 C22 C17 177.8(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4 O1 0.86(4) 2.20(4) 2.817(4) 129(3) 4_465 yes
N14 H14 O1 0.89(4) 2.14(4) 3.015(4) 168(3) 1_455 yes
C23 H23A Br1 0.96 3.11 3.620(4) 114.5 3_556 yes

_refine_diff_density_max         0.489
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.060

