# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_mo_210702_wyx05939301_0m
_database_code_depnum_ccdc_archive 'CCDC 2156024'
loop_
_audit_author_name
_audit_author_address
'Yingxiao Wang'
;Zhejiang university
China
;
_audit_update_record             
;
2022-03-03 deposited with the CCDC.	2022-10-12 downloaded from the CCDC.
;
_audit_creation_date             2021-07-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 Br N O3'
_chemical_formula_sum            'C18 H14 Br N O3'
_chemical_formula_weight         372.21
_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   17.155(5)
_cell_length_b                   4.3367(14)
_cell_length_c                   21.762(7)
_cell_angle_alpha                90
_cell_angle_beta                 110.294(14)
_cell_angle_gamma                90
_cell_volume                     1518.5(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9907
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.06
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   0.854
_shelx_estimated_absorpt_T_min   0.394
_exptl_absorpt_coefficient_mu    2.722
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1125 before and 0.0449 after correction.
The Ratio of minimum to maximum transmission is 0.6126.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            23432
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.114
_diffrn_reflns_theta_min         2.532
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3076
_reflns_number_total             3362
_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 V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_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         0.260
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0204
_refine_ls_restrained_S_all      1.056
_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)+(0.0253P)²+0.6264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0530
_refine_ls_wR_factor_ref         0.0545
_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 Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C12(H12), C13(H13), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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 0.24265(2) 0.15719(4) 0.33496(2) 0.03252(6) Uani 1 1 d . . . . .
O1 O 0.66872(6) 0.5154(2) 0.31530(5) 0.0243(2) Uani 1 1 d . . . . .
O2 O 0.62411(7) 0.9977(3) 0.47754(5) 0.0355(3) Uani 1 1 d . . . . .
O3 O 0.71938(6) 0.8751(2) 0.43153(5) 0.0281(2) Uani 1 1 d . . . . .
N1 N 0.47215(7) 0.3833(3) 0.32969(6) 0.0215(2) Uani 1 1 d . . . . .
C1 C 0.45891(9) 0.6538(3) 0.42265(7) 0.0259(3) Uani 1 1 d . . . . .
H1 H 0.481134 0.787667 0.459121 0.031 Uiso 1 1 calc R . . . .
C2 C 0.38116(9) 0.5324(4) 0.40903(7) 0.0268(3) Uani 1 1 d . . . . .
H2 H 0.348829 0.582568 0.435331 0.032 Uiso 1 1 calc R . . . .
C3 C 0.35001(9) 0.3314(3) 0.35515(7) 0.0252(3) Uani 1 1 d . . . . .
C4 C 0.39470(8) 0.2542(3) 0.31648(7) 0.0241(3) Uani 1 1 d . . . . .
H4 H 0.372876 0.114024 0.281094 0.029 Uiso 1 1 calc R . . . .
C5 C 0.50648(9) 0.5822(3) 0.38310(7) 0.0227(3) Uani 1 1 d . . . . .
C6 C 0.58744(9) 0.6616(3) 0.38590(7) 0.0232(3) Uani 1 1 d . . . . .
C7 C 0.60021(8) 0.5024(3) 0.33351(7) 0.0218(3) Uani 1 1 d . . . . .
C8 C 0.52968(8) 0.3383(3) 0.29819(7) 0.0222(3) Uani 1 1 d . . . . .
C9 C 0.51974(9) 0.1979(3) 0.23558(7) 0.0224(3) Uani 1 1 d . . . . .
C10 C 0.59506(9) 0.1686(3) 0.22334(7) 0.0228(3) Uani 1 1 d . . . . .
C11 C 0.67497(8) 0.2442(3) 0.27811(7) 0.0231(3) Uani 1 1 d . . . . .
H11A H 0.691396 0.065533 0.308175 0.028 Uiso 1 1 calc R . . . .
H11B H 0.719296 0.278123 0.259406 0.028 Uiso 1 1 calc R . . . .
C12 C 0.44542(9) 0.1147(4) 0.18629(7) 0.0280(3) Uani 1 1 d . . . . .
H12 H 0.394068 0.139480 0.193219 0.034 Uiso 1 1 calc R . . . .
C13 C 0.44639(9) -0.0040(4) 0.12732(8) 0.0346(4) Uani 1 1 d . . . . .
H13 H 0.395809 -0.066740 0.094753 0.042 Uiso 1 1 calc R . . . .
C14 C 0.52038(10) -0.0319(4) 0.11547(8) 0.0369(4) Uani 1 1 d . . . . .
H14 H 0.520479 -0.112351 0.074894 0.044 Uiso 1 1 calc R . . . .
C15 C 0.59477(9) 0.0586(4) 0.16339(7) 0.0301(3) Uani 1 1 d . . . . .
H15 H 0.645400 0.044786 0.154948 0.036 Uiso 1 1 calc R . . . .
C16 C 0.64272(9) 0.8610(3) 0.43603(7) 0.0246(3) Uani 1 1 d . . . . .
C17 C 0.77931(10) 1.0658(4) 0.48000(8) 0.0333(3) Uani 1 1 d . . . . .
H17A H 0.782754 1.005404 0.524737 0.040 Uiso 1 1 calc R . . . .
H17B H 0.763194 1.285755 0.473198 0.040 Uiso 1 1 calc R . . . .
C18 C 0.86128(10) 1.0139(5) 0.47094(9) 0.0414(4) Uani 1 1 d . . . . .
H18A H 0.856899 1.075523 0.426538 0.062 Uiso 1 1 calc GR . . . .
H18B H 0.876073 0.795081 0.477426 0.062 Uiso 1 1 calc GR . . . .
H18C H 0.904306 1.137448 0.502957 0.062 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 C3 1.8959(15) . ?
O1 C7 1.3655(16) . ?
O1 C11 1.4525(17) . ?
O2 C16 1.2120(18) . ?
O3 C16 1.3535(18) . ?
O3 C17 1.4495(18) . ?
N1 C4 1.3771(18) . ?
N1 C5 1.4024(18) . ?
N1 C8 1.3971(17) . ?
C1 H1 0.9500 . ?
C1 C2 1.367(2) . ?
C1 C5 1.411(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.409(2) . ?
C3 C4 1.362(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.412(2) . ?
C6 C7 1.4134(19) . ?
C6 C16 1.456(2) . ?
C7 C8 1.384(2) . ?
C8 C9 1.447(2) . ?
C9 C10 1.4127(19) . ?
C9 C12 1.399(2) . ?
C10 C11 1.508(2) . ?
C10 C15 1.387(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12 0.9500 . ?
C12 C13 1.388(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.395(2) . ?
C15 H15 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.503(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C7 O1 C11 111.45(10) . . ?
C16 O3 C17 115.78(12) . . ?
C4 N1 C5 121.37(12) . . ?
C4 N1 C8 129.44(12) . . ?
C8 N1 C5 109.12(11) . . ?
C2 C1 H1 119.7 . . ?
C2 C1 C5 120.68(14) . . ?
C5 C1 H1 119.7 . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.57(13) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 Br1 119.80(11) . . ?
C4 C3 Br1 117.93(11) . . ?
C4 C3 C2 122.27(13) . . ?
N1 C4 H4 120.7 . . ?
C3 C4 N1 118.68(13) . . ?
C3 C4 H4 120.7 . . ?
N1 C5 C1 118.39(13) . . ?
N1 C5 C6 108.05(12) . . ?
C1 C5 C6 133.52(13) . . ?
C5 C6 C7 105.76(12) . . ?
C5 C6 C16 123.55(13) . . ?
C7 C6 C16 130.66(13) . . ?
O1 C7 C6 127.15(12) . . ?
O1 C7 C8 122.31(12) . . ?
C8 C7 C6 110.41(12) . . ?
N1 C8 C9 130.40(13) . . ?
C7 C8 N1 106.61(12) . . ?
C7 C8 C9 122.27(12) . . ?
C10 C9 C8 113.48(12) . . ?
C12 C9 C8 127.50(13) . . ?
C12 C9 C10 118.83(13) . . ?
C9 C10 C11 118.14(12) . . ?
C15 C10 C9 120.19(13) . . ?
C15 C10 C11 121.59(13) . . ?
O1 C11 C10 113.20(11) . . ?
O1 C11 H11A 108.9 . . ?
O1 C11 H11B 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.8 . . ?
C9 C12 H12 119.9 . . ?
C13 C12 C9 120.29(14) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.66(14) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.73(14) . . ?
C15 C14 H14 120.1 . . ?
C10 C15 C14 120.24(14) . . ?
C10 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
O2 C16 O3 123.06(13) . . ?
O2 C16 C6 125.26(14) . . ?
O3 C16 C6 111.68(12) . . ?
O3 C17 H17A 110.5 . . ?
O3 C17 H17B 110.5 . . ?
O3 C17 C18 106.21(13) . . ?
H17A C17 H17B 108.7 . . ?
C18 C17 H17A 110.5 . . ?
C18 C17 H17B 110.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
Br1 C3 C4 N1 178.76(10) . . . . ?
O1 C7 C8 N1 -178.39(12) . . . . ?
O1 C7 C8 C9 -7.2(2) . . . . ?
N1 C5 C6 C7 -0.64(15) . . . . ?
N1 C5 C6 C16 -178.83(12) . . . . ?
N1 C8 C9 C10 -174.28(13) . . . . ?
N1 C8 C9 C12 10.9(2) . . . . ?
C1 C2 C3 Br1 179.73(11) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C1 C5 C6 C7 177.04(15) . . . . ?
C1 C5 C6 C16 -1.2(2) . . . . ?
C2 C1 C5 N1 -0.2(2) . . . . ?
C2 C1 C5 C6 -177.64(15) . . . . ?
C2 C3 C4 N1 -1.6(2) . . . . ?
C4 N1 C5 C1 -1.40(19) . . . . ?
C4 N1 C5 C6 176.69(12) . . . . ?
C4 N1 C8 C7 -175.35(13) . . . . ?
C4 N1 C8 C9 14.4(2) . . . . ?
C5 N1 C4 C3 2.3(2) . . . . ?
C5 N1 C8 C7 1.74(15) . . . . ?
C5 N1 C8 C9 -168.48(14) . . . . ?
C5 C1 C2 C3 0.8(2) . . . . ?
C5 C6 C7 O1 177.75(13) . . . . ?
C5 C6 C7 C8 1.76(16) . . . . ?
C5 C6 C16 O2 -5.6(2) . . . . ?
C5 C6 C16 O3 173.76(12) . . . . ?
C6 C7 C8 N1 -2.18(16) . . . . ?
C6 C7 C8 C9 169.02(12) . . . . ?
C7 O1 C11 C10 48.97(15) . . . . ?
C7 C6 C16 O2 176.71(15) . . . . ?
C7 C6 C16 O3 -3.9(2) . . . . ?
C7 C8 C9 C10 16.82(19) . . . . ?
C7 C8 C9 C12 -157.97(15) . . . . ?
C8 N1 C4 C3 179.03(13) . . . . ?
C8 N1 C5 C1 -178.76(12) . . . . ?
C8 N1 C5 C6 -0.67(15) . . . . ?
C8 C9 C10 C11 7.71(18) . . . . ?
C8 C9 C10 C15 -175.40(13) . . . . ?
C8 C9 C12 C13 176.65(15) . . . . ?
C9 C10 C11 O1 -40.89(17) . . . . ?
C9 C10 C15 C14 -1.8(2) . . . . ?
C9 C12 C13 C14 -2.2(3) . . . . ?
C10 C9 C12 C13 2.1(2) . . . . ?
C11 O1 C7 C6 157.64(13) . . . . ?
C11 O1 C7 C8 -26.82(17) . . . . ?
C11 C10 C15 C14 175.01(15) . . . . ?
C12 C9 C10 C11 -177.00(13) . . . . ?
C12 C9 C10 C15 -0.1(2) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C10 1.7(3) . . . . ?
C15 C10 C11 O1 142.27(14) . . . . ?
C16 O3 C17 C18 172.89(13) . . . . ?
C16 C6 C7 O1 -4.2(2) . . . . ?
C16 C6 C7 C8 179.78(14) . . . . ?
C17 O3 C16 O2 0.1(2) . . . . ?
C17 O3 C16 C6 -179.29(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
