# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_bb146
_database_code_depnum_ccdc_archive 'CCDC 2245738'
loop_
_audit_author_name
_audit_author_address
'Biswajit Bhattacharya'
;BAM Federal Institute for Materials Research and Testing
Germany
;
_audit_update_record             
;
2023-03-02 deposited with the CCDC.	2023-05-01 downloaded from the CCDC.
;
_audit_creation_date             2022-02-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H15 Br N2 O'
_chemical_formula_sum            'C22 H15 Br N2 O'
_chemical_formula_weight         403.27
_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'
O O 0.0106 0.0060 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   4.3315(4)
_cell_length_b                   18.5293(17)
_cell_length_c                   21.324(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.751(4)
_cell_angle_gamma                90
_cell_volume                     1707.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    400
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      26.72
_cell_measurement_theta_min      2.21
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.420
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Neddle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          00.11
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            64457
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.723
_diffrn_reflns_theta_min         2.207
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2786
_reflns_number_total             3620
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.850
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3620
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.038
_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)+(0.0522P)²+1.6924P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1149
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C19(H19), C18(H18), C9(H9), C4(H4), C22(H22), C21(H21), C7(H7),
 C5(H5), C1(H1), C6(H6), C11(H11), C14(H14), C12(H12), C13(H13)
;
_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
Br1 Br 0.06344(8) -0.00393(2) 0.40016(2) 0.05555(15) Uani 1 1 d . . . . .
O1 O 0.8291(5) 0.31327(12) 0.37681(10) 0.0471(5) Uani 1 1 d . . . . .
N2 N 0.8661(6) 0.30811(12) 0.48376(11) 0.0373(5) Uani 1 1 d . . . . .
H2 H 0.7948 0.2886 0.5175 0.045 Uiso 1 1 calc R U . . .
N1 N 1.0798(6) 0.36274(14) 0.48927(12) 0.0423(6) Uani 1 1 d . . . . .
C3 C 1.0475(7) 0.29907(14) 0.63144(13) 0.0341(6) Uani 1 1 d . . . . .
C17 C 0.5728(7) 0.21683(16) 0.42457(13) 0.0365(6) Uani 1 1 d . . . . .
C8 C 0.9191(7) 0.28443(15) 0.69082(13) 0.0369(6) Uani 1 1 d . . . . .
C15 C 0.8389(7) 0.42239(15) 0.63520(14) 0.0371(6) Uani 1 1 d . . . . .
C19 C 0.4420(7) 0.10035(16) 0.46603(14) 0.0413(7) Uani 1 1 d . . . . .
H19 H 0.4594 0.0654 0.4987 0.050 Uiso 1 1 calc R U . . .
C10 C 0.7090(7) 0.40603(15) 0.69362(14) 0.0397(7) Uani 1 1 d . . . . .
C18 C 0.6007(7) 0.16490(15) 0.47196(14) 0.0387(7) Uani 1 1 d . . . . .
H18 H 0.7305 0.1740 0.5088 0.046 Uiso 1 1 calc R U . . .
C2 C 1.0011(7) 0.36862(14) 0.60435(13) 0.0350(6) Uani 1 1 d . . . . .
C9 C 0.7514(7) 0.33734(16) 0.71953(14) 0.0397(7) Uani 1 1 d . . . . .
H9 H 0.6627 0.3265 0.7580 0.048 Uiso 1 1 calc R U . . .
C16 C 0.7647(7) 0.28421(16) 0.42519(13) 0.0383(7) Uani 1 1 d . . . . .
C20 C 0.2577(7) 0.08728(16) 0.41196(14) 0.0408(7) Uani 1 1 d . . . . .
C4 C 1.2192(7) 0.24391(15) 0.60361(15) 0.0390(7) Uani 1 1 d . . . . .
H4 H 1.3045 0.2527 0.5644 0.047 Uiso 1 1 calc R U . . .
C22 C 0.3771(7) 0.20305(17) 0.37141(14) 0.0411(7) Uani 1 1 d . . . . .
H22 H 0.3520 0.2384 0.3392 0.049 Uiso 1 1 calc R U . . .
C21 C 0.2196(7) 0.13846(18) 0.36518(15) 0.0444(7) Uani 1 1 d . . . . .
H21 H 0.0860 0.1293 0.3289 0.053 Uiso 1 1 calc R U . . .
C7 C 0.9723(8) 0.21501(16) 0.71884(14) 0.0447(8) Uani 1 1 d . . . . .
H7 H 0.8889 0.2044 0.7579 0.054 Uiso 1 1 calc R U . . .
C5 C 1.2644(8) 0.17845(16) 0.63199(16) 0.0452(7) Uani 1 1 d . . . . .
H5 H 1.3799 0.1422 0.6125 0.054 Uiso 1 1 calc R U . . .
C1 C 1.1393(7) 0.38815(16) 0.54454(15) 0.0415(7) Uani 1 1 d . . . . .
H1 H 1.2935 0.4247 0.5479 0.050 Uiso 1 1 calc R U . . .
C6 C 1.1394(8) 0.16434(16) 0.69060(16) 0.0487(8) Uani 1 1 d . . . . .
H6 H 1.1736 0.1187 0.7102 0.058 Uiso 1 1 calc R U . . .
C11 C 0.5367(8) 0.46060(18) 0.72356(17) 0.0504(8) Uani 1 1 d . . . . .
H11 H 0.4472 0.4502 0.7620 0.061 Uiso 1 1 calc R U . . .
C14 C 0.7973(8) 0.49354(15) 0.61055(17) 0.0458(7) Uani 1 1 d . . . . .
H14 H 0.8854 0.5059 0.5723 0.055 Uiso 1 1 calc R U . . .
C12 C 0.5001(8) 0.52743(19) 0.69737(19) 0.0577(10) Uani 1 1 d . . . . .
H12 H 0.3836 0.5631 0.7174 0.069 Uiso 1 1 calc R U . . .
C13 C 0.6351(8) 0.54364(17) 0.64054(19) 0.0557(9) Uani 1 1 d . . . . .
H13 H 0.6113 0.5906 0.6231 0.067 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 C20 1.897(3) . ?
O1 C16 1.212(3) . ?
N2 H2 0.8800 . ?
N2 N1 1.371(4) . ?
N2 C16 1.370(4) . ?
N1 C1 1.280(4) . ?
C3 C8 1.442(4) . ?
C3 C2 1.421(4) . ?
C3 C4 1.417(4) . ?
C17 C18 1.395(4) . ?
C17 C16 1.500(4) . ?
C17 C22 1.394(4) . ?
C8 C9 1.386(4) . ?
C8 C7 1.431(4) . ?
C15 C10 1.432(4) . ?
C15 C2 1.407(4) . ?
C15 C14 1.426(4) . ?
C19 H19 0.9500 . ?
C19 C18 1.381(4) . ?
C19 C20 1.380(4) . ?
C10 C9 1.395(4) . ?
C10 C11 1.432(4) . ?
C18 H18 0.9500 . ?
C2 C1 1.488(4) . ?
C9 H9 0.9500 . ?
C20 C21 1.378(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.364(4) . ?
C22 H22 0.9500 . ?
C22 C21 1.380(5) . ?
C21 H21 0.9500 . ?
C7 H7 0.9500 . ?
C7 C6 1.351(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.418(5) . ?
C1 H1 0.9500 . ?
C6 H6 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.363(5) . ?
C14 H14 0.9500 . ?
C14 C13 1.350(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.412(5) . ?
C13 H13 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
N1 N2 H2 120.3 . . ?
C16 N2 H2 120.3 . . ?
C16 N2 N1 119.4(2) . . ?
C1 N1 N2 116.4(3) . . ?
C2 C3 C8 118.4(3) . . ?
C4 C3 C8 118.4(3) . . ?
C4 C3 C2 123.2(3) . . ?
C18 C17 C16 123.1(3) . . ?
C22 C17 C18 118.8(3) . . ?
C22 C17 C16 117.8(3) . . ?
C9 C8 C3 119.9(3) . . ?
C9 C8 C7 121.8(3) . . ?
C7 C8 C3 118.4(3) . . ?
C2 C15 C10 119.6(3) . . ?
C2 C15 C14 122.5(3) . . ?
C14 C15 C10 118.0(3) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C20 C19 C18 119.0(3) . . ?
C9 C10 C15 119.2(3) . . ?
C9 C10 C11 121.8(3) . . ?
C11 C10 C15 119.0(3) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.8(3) . . ?
C19 C18 H18 119.6 . . ?
C3 C2 C1 121.0(3) . . ?
C15 C2 C3 120.9(3) . . ?
C15 C2 C1 118.0(2) . . ?
C8 C9 C10 122.0(3) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 H9 119.0 . . ?
O1 C16 N2 123.7(3) . . ?
O1 C16 C17 121.4(3) . . ?
N2 C16 C17 114.9(2) . . ?
C19 C20 Br1 119.6(2) . . ?
C21 C20 Br1 119.1(2) . . ?
C21 C20 C19 121.3(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.3 . . ?
C17 C22 H22 119.7 . . ?
C21 C22 C17 120.5(3) . . ?
C21 C22 H22 119.7 . . ?
C20 C21 C22 119.5(3) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C8 C7 H7 119.5 . . ?
C6 C7 C8 121.0(3) . . ?
C6 C7 H7 119.5 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
N1 C1 C2 129.2(3) . . ?
N1 C1 H1 115.4 . . ?
C2 C1 H1 115.4 . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C15 C14 H14 119.4 . . ?
C13 C14 C15 121.2(3) . . ?
C13 C14 H14 119.4 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.1(3) . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 121.2(3) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?

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
Br1 C20 C21 C22 -175.5(2) . . . . ?
N2 N1 C1 C2 -2.3(5) . . . . ?
N1 N2 C16 O1 -7.7(4) . . . . ?
N1 N2 C16 C17 170.4(2) . . . . ?
C3 C8 C9 C10 -1.9(4) . . . . ?
C3 C8 C7 C6 0.2(4) . . . . ?
C3 C2 C1 N1 66.1(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C17 C22 C21 C20 -0.2(4) . . . . ?
C8 C3 C2 C15 1.2(4) . . . . ?
C8 C3 C2 C1 177.3(3) . . . . ?
C8 C3 C4 C5 -0.2(4) . . . . ?
C8 C7 C6 C5 -0.6(5) . . . . ?
C15 C10 C9 C8 0.8(4) . . . . ?
C15 C10 C11 C12 -0.9(4) . . . . ?
C15 C2 C1 N1 -117.7(4) . . . . ?
C15 C14 C13 C12 -0.1(5) . . . . ?
C19 C20 C21 C22 2.3(5) . . . . ?
C10 C15 C2 C3 -2.3(4) . . . . ?
C10 C15 C2 C1 -178.5(3) . . . . ?
C10 C15 C14 C13 -1.4(5) . . . . ?
C10 C11 C12 C13 -0.6(5) . . . . ?
C18 C17 C16 O1 150.9(3) . . . . ?
C18 C17 C16 N2 -27.3(4) . . . . ?
C18 C17 C22 C21 -1.5(4) . . . . ?
C18 C19 C20 Br1 175.1(2) . . . . ?
C18 C19 C20 C21 -2.7(5) . . . . ?
C2 C3 C8 C9 0.9(4) . . . . ?
C2 C3 C8 C7 -178.5(3) . . . . ?
C2 C3 C4 C5 178.4(3) . . . . ?
C2 C15 C10 C9 1.3(4) . . . . ?
C2 C15 C10 C11 -178.2(3) . . . . ?
C2 C15 C14 C13 178.6(3) . . . . ?
C9 C8 C7 C6 -179.2(3) . . . . ?
C9 C10 C11 C12 179.7(3) . . . . ?
C16 N2 N1 C1 172.4(3) . . . . ?
C16 C17 C18 C19 -173.2(3) . . . . ?
C16 C17 C22 C21 173.1(3) . . . . ?
C20 C19 C18 C17 0.9(4) . . . . ?
C4 C3 C8 C9 179.6(3) . . . . ?
C4 C3 C8 C7 0.2(4) . . . . ?
C4 C3 C2 C15 -177.5(3) . . . . ?
C4 C3 C2 C1 -1.3(4) . . . . ?
C4 C5 C6 C7 0.6(5) . . . . ?
C22 C17 C18 C19 1.1(4) . . . . ?
C22 C17 C16 O1 -23.5(4) . . . . ?
C22 C17 C16 N2 158.4(3) . . . . ?
C7 C8 C9 C10 177.5(3) . . . . ?
C11 C10 C9 C8 -179.7(3) . . . . ?
C11 C12 C13 C14 1.1(5) . . . . ?
C14 C15 C10 C9 -178.7(3) . . . . ?
C14 C15 C10 C11 1.8(4) . . . . ?
C14 C15 C2 C3 177.7(3) . . . . ?
C14 C15 C2 C1 1.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
