# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2091504'
loop_
_audit_author_name
_audit_author_address
'Mengfei Zhao'
;Jilin University
China
;
_audit_update_record             
;
2021-06-22 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;
_audit_creation_date             2021-06-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H16 Br N3 O'
_chemical_formula_sum            'C20 H16 Br N3 O'
_chemical_formula_weight         394.27
_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                   13.4703(3)
_cell_length_b                   14.2884(3)
_cell_length_c                   9.0192(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.1980(10)
_cell_angle_gamma                90
_cell_volume                     1722.24(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    180.0
_cell_measurement_theta_max      25.022
_cell_measurement_theta_min      2.686
_shelx_estimated_absorpt_T_max   0.831
_shelx_estimated_absorpt_T_min   0.795
_exptl_absorpt_coefficient_mu    2.400
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0926 before and 0.0443 after correction.
The Ratio of minimum to maximum transmission is 0.8261.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            22961
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.040
_diffrn_reflns_theta_min         2.087
_diffrn_ambient_temperature      180.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2770
_reflns_number_total             3013
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3013
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0221
_refine_ls_restrained_S_all      1.046
_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)+(0.0262P)²+1.1080P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0556
_refine_ls_wR_factor_ref         0.0574
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C8(H8), C10(H10), C14(H14), C3(H3A), C7(H7), C15(H15), C2(H2), C9(H9),
  C19(H19)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C)
;
_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 0.23372(2) 0.48555(2) -0.06975(2) 0.02978(8) Uani 1 1 d . . . . .
O1 O 0.40468(9) 0.34200(10) 0.02996(14) 0.0272(3) Uani 1 1 d . . . . .
N1 N 0.44111(10) 0.37880(10) 0.56360(16) 0.0200(3) Uani 1 1 d . . . . .
N3 N 0.40546(10) 0.32984(10) 0.28251(16) 0.0204(3) Uani 1 1 d . . . . .
H3 H 0.3662 0.3159 0.3503 0.024 Uiso 1 1 calc R U . . .
C1 C 0.52368(12) 0.37333(11) 0.48944(18) 0.0176(3) Uani 1 1 d . . . . .
N2 N 0.87220(13) 0.33938(14) 0.7892(2) 0.0391(4) Uani 1 1 d . . . . .
C4 C 0.62195(12) 0.39485(11) 0.55630(19) 0.0179(3) Uani 1 1 d . . . . .
C6 C 0.36053(13) 0.33357(12) 0.13893(19) 0.0197(4) Uani 1 1 d . . . . .
C8 C 0.63070(13) 0.42280(12) 0.70867(19) 0.0219(4) Uani 1 1 d . . . . .
H8 H 0.6944 0.4389 0.7597 0.026 Uiso 1 1 calc R U . . .
C10 C 0.68290(13) 0.35556(12) 0.32431(19) 0.0217(4) Uani 1 1 d . . . . .
H10 H 0.7371 0.3471 0.2676 0.026 Uiso 1 1 calc R U . . .
C12 C 0.24857(13) 0.32629(12) 0.12863(18) 0.0197(4) Uani 1 1 d . . . . .
C14 C 0.58508(13) 0.33555(12) 0.25593(19) 0.0216(4) Uani 1 1 d . . . . .
H14 H 0.5742 0.3154 0.1548 0.026 Uiso 1 1 calc R U . . .
C16 C 0.50615(12) 0.34539(12) 0.33629(18) 0.0185(3) Uani 1 1 d . . . . .
C18 C 0.81236(15) 0.52546(13) 0.5518(2) 0.0295(4) Uani 1 1 d . . . . .
H18A H 0.7986 0.5560 0.4541 0.044 Uiso 1 1 calc R U . . .
H18B H 0.8786 0.5445 0.5998 0.044 Uiso 1 1 calc R U . . .
H18C H 0.7615 0.5440 0.6148 0.044 Uiso 1 1 calc R U . . .
C20 C 0.70338(12) 0.38670(12) 0.46871(19) 0.0188(4) Uani 1 1 d . . . . .
C5 C 0.18406(14) 0.38737(12) 0.04322(19) 0.0219(4) Uani 1 1 d . . . . .
C11 C 0.80991(13) 0.41821(13) 0.5309(2) 0.0219(4) Uani 1 1 d . . . . .
C3 C 0.45443(13) 0.40428(13) 0.7046(2) 0.0232(4) Uani 1 1 d . . . . .
H3A H 0.3975 0.4077 0.7568 0.028 Uiso 1 1 calc R U . . .
C13 C 0.84216(13) 0.37306(13) 0.6774(2) 0.0256(4) Uani 1 1 d . . . . .
C7 C 0.20534(14) 0.25702(13) 0.2094(2) 0.0264(4) Uani 1 1 d . . . . .
H7 H 0.2474 0.2146 0.2692 0.032 Uiso 1 1 calc R U . . .
C15 C 0.54822(14) 0.42673(13) 0.7821(2) 0.0242(4) Uani 1 1 d . . . . .
H15 H 0.5542 0.4444 0.8844 0.029 Uiso 1 1 calc R U . . .
C2 C 0.08137(14) 0.38057(14) 0.0383(2) 0.0282(4) Uani 1 1 d . . . . .
H2 H 0.0390 0.4234 -0.0200 0.034 Uiso 1 1 calc R U . . .
C17 C 0.89015(13) 0.39053(14) 0.4313(2) 0.0282(4) Uani 1 1 d . . . . .
H17A H 0.8788 0.4251 0.3369 0.042 Uiso 1 1 calc R U . . .
H17B H 0.8860 0.3232 0.4110 0.042 Uiso 1 1 calc R U . . .
H17C H 0.9566 0.4057 0.4828 0.042 Uiso 1 1 calc R U . . .
C9 C 0.10249(15) 0.24908(15) 0.2039(2) 0.0333(5) Uani 1 1 d . . . . .
H9 H 0.0745 0.2011 0.2585 0.040 Uiso 1 1 calc R U . . .
C19 C 0.04059(14) 0.31117(15) 0.1187(2) 0.0326(5) Uani 1 1 d . . . . .
H19 H -0.0300 0.3061 0.1154 0.039 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 C5 1.9038(18) . ?
O1 C6 1.217(2) . ?
N1 C1 1.370(2) . ?
N1 C3 1.313(2) . ?
N3 H3 0.8800 . ?
N3 C6 1.360(2) . ?
N3 C16 1.400(2) . ?
C1 C4 1.418(2) . ?
C1 C16 1.429(2) . ?
N2 C13 1.145(3) . ?
C4 C8 1.422(2) . ?
C4 C20 1.435(2) . ?
C6 C12 1.503(2) . ?
C8 H8 0.9500 . ?
C8 C15 1.364(3) . ?
C10 H10 0.9500 . ?
C10 C14 1.412(2) . ?
C10 C20 1.371(2) . ?
C12 C5 1.394(2) . ?
C12 C7 1.398(3) . ?
C14 H14 0.9500 . ?
C14 C16 1.367(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 C11 1.544(3) . ?
C20 C11 1.541(2) . ?
C5 C2 1.382(3) . ?
C11 C13 1.486(3) . ?
C11 C17 1.541(2) . ?
C3 H3A 0.9500 . ?
C3 C15 1.402(3) . ?
C7 H7 0.9500 . ?
C7 C9 1.385(3) . ?
C15 H15 0.9500 . ?
C2 H2 0.9500 . ?
C2 C19 1.382(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C9 H9 0.9500 . ?
C9 C19 1.383(3) . ?
C19 H19 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
C3 N1 C1 117.89(15) . . ?
C6 N3 H3 115.8 . . ?
C6 N3 C16 128.32(15) . . ?
C16 N3 H3 115.8 . . ?
N1 C1 C4 123.49(15) . . ?
N1 C1 C16 116.23(15) . . ?
C4 C1 C16 120.27(15) . . ?
C1 C4 C8 115.59(15) . . ?
C1 C4 C20 119.06(15) . . ?
C8 C4 C20 125.35(15) . . ?
O1 C6 N3 124.66(16) . . ?
O1 C6 C12 123.03(15) . . ?
N3 C6 C12 112.31(14) . . ?
C4 C8 H8 119.8 . . ?
C15 C8 C4 120.46(16) . . ?
C15 C8 H8 119.8 . . ?
C14 C10 H10 118.5 . . ?
C20 C10 H10 118.5 . . ?
C20 C10 C14 123.10(16) . . ?
C5 C12 C6 122.83(16) . . ?
C5 C12 C7 117.36(16) . . ?
C7 C12 C6 119.79(16) . . ?
C10 C14 H14 120.2 . . ?
C16 C14 C10 119.52(16) . . ?
C16 C14 H14 120.2 . . ?
N3 C16 C1 114.52(14) . . ?
C14 C16 N3 125.74(16) . . ?
C14 C16 C1 119.74(15) . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 C18 H18A 109.5 . . ?
C11 C18 H18B 109.5 . . ?
C11 C18 H18C 109.5 . . ?
C4 C20 C11 121.14(15) . . ?
C10 C20 C4 118.21(15) . . ?
C10 C20 C11 120.52(15) . . ?
C12 C5 Br1 121.38(13) . . ?
C2 C5 Br1 116.89(14) . . ?
C2 C5 C12 121.73(17) . . ?
C20 C11 C18 109.82(14) . . ?
C13 C11 C18 108.84(15) . . ?
C13 C11 C20 110.62(14) . . ?
C13 C11 C17 104.99(15) . . ?
C17 C11 C18 108.67(15) . . ?
C17 C11 C20 113.71(15) . . ?
N1 C3 H3A 118.3 . . ?
N1 C3 C15 123.47(16) . . ?
C15 C3 H3A 118.3 . . ?
N2 C13 C11 176.33(19) . . ?
C12 C7 H7 119.4 . . ?
C9 C7 C12 121.28(18) . . ?
C9 C7 H7 119.4 . . ?
C8 C15 C3 119.08(16) . . ?
C8 C15 H15 120.5 . . ?
C3 C15 H15 120.5 . . ?
C5 C2 H2 120.1 . . ?
C5 C2 C19 119.73(18) . . ?
C19 C2 H2 120.1 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7 C9 H9 120.1 . . ?
C19 C9 C7 119.90(18) . . ?
C19 C9 H9 120.1 . . ?
C2 C19 C9 120.00(18) . . ?
C2 C19 H19 120.0 . . ?
C9 C19 H19 120.0 . . ?

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 C5 C2 C19 -179.59(14) . . . . ?
O1 C6 C12 C5 -48.2(3) . . . . ?
O1 C6 C12 C7 133.14(19) . . . . ?
N1 C1 C4 C8 0.3(2) . . . . ?
N1 C1 C4 C20 179.90(15) . . . . ?
N1 C1 C16 N3 1.6(2) . . . . ?
N1 C1 C16 C14 -178.03(15) . . . . ?
N1 C3 C15 C8 0.4(3) . . . . ?
N3 C6 C12 C5 131.71(17) . . . . ?
N3 C6 C12 C7 -47.0(2) . . . . ?
C1 N1 C3 C15 0.5(3) . . . . ?
C1 C4 C8 C15 0.7(2) . . . . ?
C1 C4 C20 C10 -1.9(2) . . . . ?
C1 C4 C20 C11 174.05(15) . . . . ?
C4 C1 C16 N3 -177.55(15) . . . . ?
C4 C1 C16 C14 2.8(2) . . . . ?
C4 C8 C15 C3 -1.0(3) . . . . ?
C4 C20 C11 C18 -66.8(2) . . . . ?
C4 C20 C11 C13 53.4(2) . . . . ?
C4 C20 C11 C17 171.20(15) . . . . ?
C6 N3 C16 C1 156.01(17) . . . . ?
C6 N3 C16 C14 -24.4(3) . . . . ?
C6 C12 C5 Br1 0.5(2) . . . . ?
C6 C12 C5 C2 -178.46(16) . . . . ?
C6 C12 C7 C9 179.21(17) . . . . ?
C8 C4 C20 C10 177.72(17) . . . . ?
C8 C4 C20 C11 -6.3(3) . . . . ?
C10 C14 C16 N3 178.73(16) . . . . ?
C10 C14 C16 C1 -1.7(3) . . . . ?
C10 C20 C11 C18 109.05(19) . . . . ?
C10 C20 C11 C13 -130.79(17) . . . . ?
C10 C20 C11 C17 -13.0(2) . . . . ?
C12 C5 C2 C19 -0.6(3) . . . . ?
C12 C7 C9 C19 -0.8(3) . . . . ?
C14 C10 C20 C4 3.1(3) . . . . ?
C14 C10 C20 C11 -172.84(16) . . . . ?
C16 N3 C6 O1 8.2(3) . . . . ?
C16 N3 C6 C12 -171.71(16) . . . . ?
C16 C1 C4 C8 179.36(15) . . . . ?
C16 C1 C4 C20 -1.0(2) . . . . ?
C20 C4 C8 C15 -178.93(17) . . . . ?
C20 C10 C14 C16 -1.4(3) . . . . ?
C5 C12 C7 C9 0.4(3) . . . . ?
C5 C2 C19 C9 0.2(3) . . . . ?
C3 N1 C1 C4 -0.8(2) . . . . ?
C3 N1 C1 C16 -179.99(15) . . . . ?
C7 C12 C5 Br1 179.23(13) . . . . ?
C7 C12 C5 C2 0.3(3) . . . . ?
C7 C9 C19 C2 0.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Petroleum ether/ethyl acetate'
