# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# 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_211211d
_database_code_depnum_ccdc_archive 'CCDC 2212904'
loop_
_audit_author_name
_audit_author_address
'Lanzhi Wang'
;Xiao Zhang
China
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2023-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 Br2 N3 O2'
_chemical_formula_weight         495.22

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.7492(9)
_cell_length_b                   21.4852(19)
_cell_length_c                   8.9772(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.765(3)
_cell_angle_gamma                90.00
_cell_volume                     2066.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2423
_cell_measurement_theta_min      2.687
_cell_measurement_theta_max      26.918

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    3.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3157
_exptl_absorpt_correction_T_max  0.6709
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9916
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_av_sigmaI/netI    0.0908
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3630
_reflns_number_gt                1881
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0954P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3630
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.0675
_refine_ls_wR_factor_ref         0.2001
_refine_ls_wR_factor_gt          0.1806
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.003
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.54078(11) 0.16258(4) 0.52035(11) 0.0980(5) Uani 1 1 d . . .
Br2 Br 0.11931(11) 0.30404(5) -0.04201(11) 0.1022(4) Uani 1 1 d . . .
N1 N 0.3304(5) 0.5023(2) 0.9220(6) 0.0538(14) Uani 1 1 d . . .
H1 H 0.3731 0.5034 1.0073 0.065 Uiso 1 1 calc R . .
N2 N 0.0909(5) 0.4359(2) 0.5621(6) 0.0528(14) Uani 1 1 d . . .
H2 H 0.0147 0.4398 0.5831 0.063 Uiso 1 1 calc R . .
N3 N 0.3033(5) 0.4582(2) 0.3873(5) 0.0461(13) Uani 1 1 d . . .
H3 H 0.3590 0.4598 0.3179 0.055 Uiso 1 1 d R . .
O1 O 0.5019(4) 0.4784(2) 0.8019(5) 0.0572(12) Uani 1 1 d . . .
O2 O 0.8295(5) 0.0762(3) 0.1351(9) 0.100(2) Uani 1 1 d . . .
H2C H 0.7813 0.0471 0.1167 0.150 Uiso 1 1 calc R . .
C1 C 0.3854(7) 0.4817(3) 0.8000(7) 0.0470(16) Uani 1 1 d . . .
C2 C 0.2021(7) 0.5225(4) 0.9113(9) 0.072(2) Uani 1 1 d . . .
H2A H 0.1965 0.5642 0.8694 0.086 Uiso 1 1 calc R . .
H2B H 0.1728 0.5242 1.0105 0.086 Uiso 1 1 calc R . .
C3 C 0.1181(6) 0.4783(3) 0.8126(8) 0.0614(19) Uani 1 1 d . . .
H3C H 0.1013 0.4414 0.8696 0.074 Uiso 1 1 calc R . .
H3D H 0.0390 0.4987 0.7851 0.074 Uiso 1 1 calc R . .
C4 C 0.1779(6) 0.4591(3) 0.6699(7) 0.0453(15) Uani 1 1 d . . .
C5 C 0.3044(6) 0.4625(3) 0.6648(7) 0.0430(15) Uani 1 1 d . . .
C6 C 0.3727(6) 0.4412(3) 0.5352(6) 0.0440(15) Uani 1 1 d . . .
H6 H 0.4498 0.4658 0.5404 0.053 Uiso 1 1 calc R . .
C7 C 0.4150(6) 0.3728(3) 0.5364(7) 0.0426(15) Uani 1 1 d . . .
C8 C 0.5053(7) 0.3536(3) 0.4445(8) 0.0571(18) Uani 1 1 d . . .
H8 H 0.5418 0.3825 0.3847 0.068 Uiso 1 1 calc R . .
C9 C 0.5418(7) 0.2915(3) 0.4409(9) 0.070(2) Uani 1 1 d . . .
H9 H 0.6023 0.2793 0.3785 0.084 Uiso 1 1 calc R . .
C10 C 0.4893(7) 0.2480(3) 0.5289(8) 0.0594(19) Uani 1 1 d . . .
C11 C 0.4003(7) 0.2653(3) 0.6192(8) 0.0609(19) Uani 1 1 d . . .
H11 H 0.3645 0.2357 0.6779 0.073 Uiso 1 1 calc R . .
C12 C 0.3620(6) 0.3275(3) 0.6251(7) 0.0519(17) Uani 1 1 d . . .
H12 H 0.3013 0.3390 0.6878 0.062 Uiso 1 1 calc R . .
C13 C 0.1058(6) 0.4067(3) 0.4213(7) 0.0457(16) Uani 1 1 d . . .
C14 C 0.2061(6) 0.4163(3) 0.3358(7) 0.0456(15) Uani 1 1 d . . .
C15 C 0.2088(7) 0.3855(3) 0.1957(8) 0.0584(18) Uani 1 1 d . . .
H15 H 0.2765 0.3908 0.1388 0.070 Uiso 1 1 calc R . .
C16 C 0.1114(8) 0.3480(3) 0.1451(8) 0.063(2) Uani 1 1 d . . .
C17 C 0.0093(8) 0.3395(3) 0.2243(9) 0.065(2) Uani 1 1 d . . .
H17 H -0.0571 0.3149 0.1864 0.078 Uiso 1 1 calc R . .
C18 C 0.0070(7) 0.3683(3) 0.3621(9) 0.067(2) Uani 1 1 d . . .
H18 H -0.0615 0.3622 0.4172 0.080 Uiso 1 1 calc R . .
C19 C 0.7745(9) 0.1191(4) 0.2216(11) 0.093(3) Uani 1 1 d . . .
H19A H 0.7911 0.1074 0.3258 0.111 Uiso 1 1 calc R . .
H19B H 0.6849 0.1175 0.1980 0.111 Uiso 1 1 calc R . .
C20 C 0.8174(10) 0.1850(4) 0.2029(14) 0.120(4) Uani 1 1 d . . .
H20A H 0.9066 0.1857 0.2008 0.180 Uiso 1 1 calc R . .
H20B H 0.7939 0.2098 0.2850 0.180 Uiso 1 1 calc R . .
H20C H 0.7792 0.2016 0.1109 0.180 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
Br1 C10 1.919(7) . ?
Br2 C16 1.935(7) . ?
N1 C1 1.362(8) . ?
N1 C2 1.442(8) . ?
N1 H1 0.8600 . ?
N2 C4 1.381(8) . ?
N2 C13 1.432(8) . ?
N2 H2 0.8600 . ?
N3 C14 1.427(7) . ?
N3 C6 1.512(8) . ?
N3 H3 0.9000 . ?
O1 C1 1.253(7) . ?
O2 C19 1.370(9) . ?
O2 H2C 0.8200 . ?
C1 C5 1.492(9) . ?
C2 C3 1.539(10) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.537(9) . ?
C3 H3C 0.9700 . ?
C3 H3D 0.9700 . ?
C4 C5 1.367(8) . ?
C5 C6 1.498(8) . ?
C6 C7 1.538(8) . ?
C6 H6 0.9800 . ?
C7 C8 1.388(9) . ?
C7 C12 1.407(9) . ?
C8 C9 1.393(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.375(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.357(9) . ?
C11 C12 1.401(9) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.390(9) . ?
C13 C18 1.413(9) . ?
C14 C15 1.424(9) . ?
C15 C16 1.367(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.369(11) . ?
C17 C18 1.385(10) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.503(12) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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 N1 C2 121.4(6) . . ?
C1 N1 H1 119.3 . . ?
C2 N1 H1 119.3 . . ?
C4 N2 C13 131.1(5) . . ?
C4 N2 H2 114.4 . . ?
C13 N2 H2 114.4 . . ?
C14 N3 C6 115.3(4) . . ?
C14 N3 H3 108.1 . . ?
C6 N3 H3 107.9 . . ?
C19 O2 H2C 109.5 . . ?
O1 C1 N1 120.5(6) . . ?
O1 C1 C5 120.7(6) . . ?
N1 C1 C5 118.7(6) . . ?
N1 C2 C3 111.4(6) . . ?
N1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C2 112.3(6) . . ?
C4 C3 H3C 109.1 . . ?
C2 C3 H3C 109.1 . . ?
C4 C3 H3D 109.1 . . ?
C2 C3 H3D 109.1 . . ?
H3C C3 H3D 107.9 . . ?
C5 C4 N2 127.8(6) . . ?
C5 C4 C3 120.0(6) . . ?
N2 C4 C3 112.1(5) . . ?
C4 C5 C1 120.2(6) . . ?
C4 C5 C6 124.3(6) . . ?
C1 C5 C6 115.2(5) . . ?
C5 C6 N3 111.7(5) . . ?
C5 C6 C7 116.7(5) . . ?
N3 C6 C7 111.2(5) . . ?
C5 C6 H6 105.4 . . ?
N3 C6 H6 105.4 . . ?
C7 C6 H6 105.4 . . ?
C8 C7 C12 117.8(6) . . ?
C8 C7 C6 120.0(5) . . ?
C12 C7 C6 122.1(6) . . ?
C7 C8 C9 120.8(7) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 120.5(7) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 120.0(6) . . ?
C11 C10 Br1 120.5(6) . . ?
C9 C10 Br1 119.6(5) . . ?
C10 C11 C12 120.6(6) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 120.3(6) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C14 C13 C18 118.2(6) . . ?
C14 C13 N2 124.8(5) . . ?
C18 C13 N2 116.9(6) . . ?
C13 C14 C15 119.5(6) . . ?
C13 C14 N3 119.7(5) . . ?
C15 C14 N3 120.8(6) . . ?
C16 C15 C14 119.7(7) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 122.1(7) . . ?
C15 C16 Br2 119.2(6) . . ?
C17 C16 Br2 118.7(5) . . ?
C16 C17 C18 118.6(7) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C17 C18 C13 121.9(7) . . ?
C17 C18 H18 119.1 . . ?
C13 C18 H18 119.1 . . ?
O2 C19 C20 114.8(8) . . ?
O2 C19 H19A 108.6 . . ?
C20 C19 H19A 108.6 . . ?
O2 C19 H19B 108.6 . . ?
C20 C19 H19B 108.6 . . ?
H19A C19 H19B 107.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C2 N1 C1 O1 163.0(6) . . . . ?
C2 N1 C1 C5 -17.6(9) . . . . ?
C1 N1 C2 C3 43.0(9) . . . . ?
N1 C2 C3 C4 -43.2(9) . . . . ?
C13 N2 C4 C5 3.7(10) . . . . ?
C13 N2 C4 C3 -172.2(6) . . . . ?
C2 C3 C4 C5 22.2(9) . . . . ?
C2 C3 C4 N2 -161.6(6) . . . . ?
N2 C4 C5 C1 -172.3(5) . . . . ?
C3 C4 C5 C1 3.3(8) . . . . ?
N2 C4 C5 C6 0.4(10) . . . . ?
C3 C4 C5 C6 176.0(5) . . . . ?
O1 C1 C5 C4 172.0(5) . . . . ?
N1 C1 C5 C4 -7.4(8) . . . . ?
O1 C1 C5 C6 -1.3(8) . . . . ?
N1 C1 C5 C6 179.3(5) . . . . ?
C4 C5 C6 N3 40.3(7) . . . . ?
C1 C5 C6 N3 -146.6(5) . . . . ?
C4 C5 C6 C7 -89.1(7) . . . . ?
C1 C5 C6 C7 83.9(6) . . . . ?
C14 N3 C6 C5 -82.7(6) . . . . ?
C14 N3 C6 C7 49.6(7) . . . . ?
C5 C6 C7 C8 -163.0(6) . . . . ?
N3 C6 C7 C8 67.3(7) . . . . ?
C5 C6 C7 C12 19.1(8) . . . . ?
N3 C6 C7 C12 -110.6(6) . . . . ?
C12 C7 C8 C9 -0.1(10) . . . . ?
C6 C7 C8 C9 -178.0(6) . . . . ?
C7 C8 C9 C10 -0.2(12) . . . . ?
C8 C9 C10 C11 0.5(12) . . . . ?
C8 C9 C10 Br1 179.5(6) . . . . ?
C9 C10 C11 C12 -0.6(11) . . . . ?
Br1 C10 C11 C12 -179.6(6) . . . . ?
C10 C11 C12 C7 0.4(10) . . . . ?
C8 C7 C12 C11 0.0(10) . . . . ?
C6 C7 C12 C11 177.9(6) . . . . ?
C4 N2 C13 C14 -26.8(10) . . . . ?
C4 N2 C13 C18 157.3(6) . . . . ?
C18 C13 C14 C15 -2.7(9) . . . . ?
N2 C13 C14 C15 -178.5(6) . . . . ?
C18 C13 C14 N3 175.7(5) . . . . ?
N2 C13 C14 N3 -0.2(9) . . . . ?
C6 N3 C14 C13 60.8(7) . . . . ?
C6 N3 C14 C15 -120.9(6) . . . . ?
C13 C14 C15 C16 1.7(9) . . . . ?
N3 C14 C15 C16 -176.7(6) . . . . ?
C14 C15 C16 C17 0.8(10) . . . . ?
C14 C15 C16 Br2 -177.8(5) . . . . ?
C15 C16 C17 C18 -2.1(11) . . . . ?
Br2 C16 C17 C18 176.4(5) . . . . ?
C16 C17 C18 C13 1.0(11) . . . . ?
C14 C13 C18 C17 1.4(10) . . . . ?
N2 C13 C18 C17 177.6(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.566
_refine_diff_density_min         -1.002
_refine_diff_density_rms         0.102
