# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
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data_mj19656_0m
_database_code_depnum_ccdc_archive 'CCDC 2014026'
loop_
_audit_author_name
_audit_author_address
'Yizhan Zhai'
;Shanghai institute of Organic Chemistry,Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-07-04 deposited with the CCDC.	2021-07-16 downloaded from the CCDC.
;
_audit_creation_date             2019-10-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 Br N3 O'
_chemical_formula_sum            'C23 H18 Br N3 O'
_chemical_formula_weight         432.31
_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 0.0148 0.0070 '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 -0.9502 1.0410 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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                   7.4828(5)
_cell_length_b                   7.7696(6)
_cell_length_c                   16.9566(12)
_cell_angle_alpha                95.198(4)
_cell_angle_beta                 91.243(4)
_cell_angle_gamma                108.491(4)
_cell_volume                     929.76(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6086
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.86
_cell_measurement_theta_min      4.56
_shelx_estimated_absorpt_T_max   0.881
_shelx_estimated_absorpt_T_min   0.797
_exptl_absorpt_coefficient_mu    2.163
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1691 before and 0.0925 after correction. The Ratio of minimum to maximum transmission is 0.6244. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_unetI/netI     0.0740
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9015
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.991
_diffrn_reflns_theta_min         4.563
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2968
_reflns_number_total             3490
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         2.110
_refine_diff_density_min         -2.097
_refine_diff_density_rms         0.201
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3490
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0808
_refine_ls_restrained_S_all      1.030
_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)+(0.1960P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2228
_refine_ls_wR_factor_ref         0.2407
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C14(H14),
 C16(H16), C17(H17), C20(H20), C21(H21), C22(H22)
2.b X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_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 0.85069(8) 0.06498(6) 0.58843(3) 0.0375(3) Uani 1 1 d . . . . .
O1 O 1.0932(4) 0.2517(5) 0.00073(19) 0.0311(8) Uani 1 1 d . . . . .
N1 N 0.5548(5) 0.3419(5) 0.2051(2) 0.0220(8) Uani 1 1 d . . . . .
N2 N 0.2798(5) 0.1063(5) 0.1601(2) 0.0264(8) Uani 1 1 d . . . . .
N3 N 0.2828(5) 0.3098(5) 0.2745(2) 0.0285(9) Uani 1 1 d . . . . .
C1 C 0.4810(7) 0.7650(7) 0.2138(3) 0.0349(11) Uani 1 1 d . . . . .
H1A H 0.516172 0.694962 0.171733 0.042 Uiso 1 1 calc R . . . .
H1B H 0.423169 0.853170 0.202352 0.042 Uiso 1 1 calc R . . . .
C2 C 0.5127(6) 0.7396(6) 0.2887(3) 0.0292(10) Uani 1 1 d . . . . .
H2 H 0.475020 0.812864 0.328608 0.035 Uiso 1 1 calc R . . . .
C3 C 0.6008(6) 0.6084(6) 0.3156(3) 0.0239(9) Uani 1 1 d . . . . .
C4 C 0.6346(6) 0.6057(6) 0.3940(3) 0.0255(9) Uani 1 1 d . . . . .
H4 H 0.614030 0.701816 0.427343 0.031 Uiso 1 1 calc R . . . .
C5 C 0.6987(6) 0.4753(6) 0.4351(3) 0.0250(9) Uani 1 1 d . . . . .
C6 C 0.7570(6) 0.5232(6) 0.5154(3) 0.0262(9) Uani 1 1 d . . . . .
H6 H 0.763784 0.640546 0.539493 0.031 Uiso 1 1 calc R . . . .
C7 C 0.8050(6) 0.4025(6) 0.5603(3) 0.0291(10) Uani 1 1 d . . . . .
H7 H 0.845039 0.436554 0.614664 0.035 Uiso 1 1 calc R . . . .
C8 C 0.7936(6) 0.2328(6) 0.5250(3) 0.0266(9) Uani 1 1 d . . . . .
C9 C 0.7364(7) 0.1796(6) 0.4456(3) 0.0303(10) Uani 1 1 d . . . . .
H9 H 0.730510 0.062116 0.421980 0.036 Uiso 1 1 calc R . . . .
C10 C 0.6879(7) 0.3016(6) 0.4014(3) 0.0295(10) Uani 1 1 d . . . . .
H10 H 0.646654 0.266112 0.347274 0.035 Uiso 1 1 calc R . . . .
C11 C 0.6669(6) 0.4999(6) 0.2526(2) 0.0231(9) Uani 1 1 d . . . . .
C12 C 0.8458(6) 0.5493(6) 0.2276(2) 0.0251(9) Uani 1 1 d . . . . .
H12 H 0.948904 0.649882 0.250181 0.030 Uiso 1 1 calc R . . . .
C13 C 0.8519(6) 0.4246(6) 0.1621(3) 0.0231(9) Uani 1 1 d . . . . .
C14 C 1.0018(6) 0.4198(6) 0.1132(3) 0.0245(9) Uani 1 1 d . . . . .
H14 H 1.122780 0.509636 0.121711 0.029 Uiso 1 1 calc R . . . .
C15 C 0.9655(6) 0.2790(6) 0.0526(2) 0.0246(9) Uani 1 1 d . . . . .
C16 C 0.7858(6) 0.1440(6) 0.0413(3) 0.0263(10) Uani 1 1 d . . . . .
H16 H 0.765933 0.046260 0.000703 0.032 Uiso 1 1 calc R . . . .
C17 C 0.6377(6) 0.1509(6) 0.0882(3) 0.0251(9) Uani 1 1 d . . . . .
H17 H 0.516588 0.061309 0.079597 0.030 Uiso 1 1 calc R . . . .
C18 C 0.6733(6) 0.2945(6) 0.1486(2) 0.0220(9) Uani 1 1 d . . . . .
C19 C 0.3626(6) 0.2477(6) 0.2140(2) 0.0217(9) Uani 1 1 d . . . . .
C20 C 0.0980(6) 0.0187(6) 0.1694(3) 0.0294(10) Uani 1 1 d . . . . .
H20 H 0.033742 -0.083301 0.132684 0.035 Uiso 1 1 calc R . . . .
C21 C -0.0007(7) 0.0696(6) 0.2300(3) 0.0280(10) Uani 1 1 d . . . . .
H21 H -0.129995 0.005731 0.236103 0.034 Uiso 1 1 calc R . . . .
C22 C 0.0995(6) 0.2182(6) 0.2811(3) 0.0285(10) Uani 1 1 d . . . . .
H22 H 0.035748 0.258265 0.323152 0.034 Uiso 1 1 calc R . . . .
C23 C 1.2767(7) 0.3833(7) 0.0076(3) 0.0304(10) Uani 1 1 d . . . . .
H23A H 1.354964 0.349234 -0.032640 0.046 Uiso 1 1 calc GR . . . .
H23B H 1.334290 0.387729 0.060482 0.046 Uiso 1 1 calc GR . . . .
H23C H 1.267219 0.503479 -0.000469 0.046 Uiso 1 1 calc GR . . . .


_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 C8 1.904(5) . ?
O1 C15 1.365(5) . ?
O1 C23 1.423(6) . ?
N1 C11 1.413(5) . ?
N1 C18 1.421(5) . ?
N1 C19 1.410(5) . ?
N2 C19 1.337(6) . ?
N2 C20 1.334(6) . ?
N3 C19 1.328(5) . ?
N3 C22 1.342(6) . ?
C1 H1A 0.9500 . ?
C1 H1B 0.9500 . ?
C1 C2 1.330(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.476(6) . ?
C3 C4 1.350(6) . ?
C3 C11 1.491(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.471(6) . ?
C5 C6 1.402(6) . ?
C5 C10 1.394(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.385(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.375(6) . ?
C8 C9 1.389(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.359(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.418(6) . ?
C13 C14 1.417(6) . ?
C13 C18 1.396(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(6) . ?
C15 C16 1.415(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.390(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.399(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.380(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.373(7) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
C15 O1 C23 117.0(3) . . ?
C11 N1 C18 107.1(3) . . ?
C19 N1 C11 126.0(3) . . ?
C19 N1 C18 126.9(3) . . ?
C20 N2 C19 115.7(4) . . ?
C19 N3 C22 115.2(4) . . ?
H1A C1 H1B 120.0 . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
C1 C2 H2 116.9 . . ?
C1 C2 C3 126.2(4) . . ?
C3 C2 H2 116.9 . . ?
C2 C3 C11 116.4(4) . . ?
C4 C3 C2 119.6(4) . . ?
C4 C3 C11 123.6(4) . . ?
C3 C4 H4 115.3 . . ?
C3 C4 C5 129.4(4) . . ?
C5 C4 H4 115.3 . . ?
C6 C5 C4 117.3(4) . . ?
C10 C5 C4 124.1(4) . . ?
C10 C5 C6 118.3(4) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.2(4) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 120.5 . . ?
C8 C7 C6 118.9(4) . . ?
C8 C7 H7 120.5 . . ?
C7 C8 Br1 118.5(3) . . ?
C7 C8 C9 121.8(4) . . ?
C9 C8 Br1 119.7(3) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 C8 118.6(4) . . ?
C10 C9 H9 120.7 . . ?
C5 C10 H10 119.4 . . ?
C9 C10 C5 121.2(4) . . ?
C9 C10 H10 119.4 . . ?
N1 C11 C3 126.6(4) . . ?
C12 C11 N1 109.3(4) . . ?
C12 C11 C3 123.9(4) . . ?
C11 C12 H12 125.9 . . ?
C11 C12 C13 108.1(4) . . ?
C13 C12 H12 125.9 . . ?
C14 C13 C12 130.5(4) . . ?
C18 C13 C12 108.3(4) . . ?
C18 C13 C14 121.2(4) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 C13 117.5(4) . . ?
C15 C14 H14 121.2 . . ?
O1 C15 C14 125.5(4) . . ?
O1 C15 C16 113.7(4) . . ?
C14 C15 C16 120.8(4) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.6(4) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 121.2 . . ?
C16 C17 C18 117.6(4) . . ?
C18 C17 H17 121.2 . . ?
C13 C18 N1 107.1(3) . . ?
C13 C18 C17 121.2(4) . . ?
C17 C18 N1 131.7(4) . . ?
N2 C19 N1 116.5(4) . . ?
N3 C19 N1 116.5(4) . . ?
N3 C19 N2 127.0(4) . . ?
N2 C20 H20 118.6 . . ?
N2 C20 C21 122.9(4) . . ?
C21 C20 H20 118.6 . . ?
C20 C21 H21 122.0 . . ?
C22 C21 C20 115.9(4) . . ?
C22 C21 H21 122.0 . . ?
N3 C22 C21 123.4(4) . . ?
N3 C22 H22 118.3 . . ?
C21 C22 H22 118.3 . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
