# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
# 
#######################################################################

data_lxl-1123
_database_code_depnum_ccdc_archive 'CCDC 2173473'
loop_
_audit_author_name
_audit_author_address
'Qunli Luo'
;Southwest University
China
;
_audit_update_record             
;
2022-05-18 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;
_audit_creation_date             2020-11-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C25 H16 Br N O4'
_chemical_formula_sum            'C25 H16 Br N O4'
_chemical_formula_weight         474.30
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     'C1 H1 N1 O1 Br1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   9.50407(12)
_cell_length_b                   13.07175(19)
_cell_length_c                   16.7222(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.3725(13)
_cell_angle_gamma                90
_cell_volume                     2043.53(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9589
_cell_measurement_temperature    292.00(10)
_cell_measurement_theta_max      71.7560
_cell_measurement_theta_min      4.9280
_shelx_estimated_absorpt_T_max   0.531
_shelx_estimated_absorpt_T_min   0.454
_exptl_absorpt_coefficient_mu    3.024
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19329
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.864
_diffrn_reflns_theta_min         4.320
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -106.00  -7.00   1.00    1.00    --  -35.97 -19.00 -90.00   99
  2  ω   -103.00 -19.00   1.00    1.00    --  -35.97 -57.00  30.00   84
  3  ω    -90.00  -3.00   1.00    1.00    --  -35.97 126.00 -90.00   87
  4  ω     24.00  90.00   1.00    1.00    --   35.97-126.00 -90.00   66
  5  ω     39.00 110.00   1.00    3.27    --  107.97 -95.00 -60.00   71
  6  ω    101.00 178.00   1.00    3.27    --  107.97 112.00  30.00   77
  7  ω     38.00 129.00   1.00    3.27    --  107.97 -30.00  60.00   91
  8  ω    101.00 178.00   1.00    3.27    --  107.97 112.00 150.00   77
  9  ω    101.00 178.00   1.00    3.27    --  107.97 112.00-120.00   77
 10  ω     87.00 178.00   1.00    3.27    --  107.97  30.00-150.00   91
 11  ω     39.00 110.00   1.00    3.27    --  107.97 -95.00-180.00   71
 12  ω     87.00 178.00   1.00    3.27    --  107.97  30.00-120.00   91
 13  ω     41.00 126.00   1.00    3.27    --  107.97 -61.00  90.00   85
 14  ω    -53.00  31.00   1.00    1.00    --  -35.97  57.00  90.00   84
 15  ω   -105.00 -17.00   1.00    1.00    --  -35.97 -38.00  90.00   88
 16  ω   -104.00  -9.00   1.00    1.00    --  -35.97 -77.00-150.00   95
 17  ω     87.00 178.00   1.00    3.27    --  107.97  30.00 -60.00   91
 18  ω     70.00 178.00   1.00    3.27    --  107.97  15.00  30.00  108
 19  ω     81.00 176.00   1.00    3.27    --  107.97  77.00 120.00   95
 20  ω     38.00 112.00   1.00    3.27    --  107.97-112.00  90.00   74
 21  ω     90.00 175.00   1.00    3.27    --  107.97  61.00  60.00   85
 22  ω     87.00 178.00   1.00    3.27    --  107.97  30.00 120.00   91
 23  ω   -104.00  -9.00   1.00    1.00    --  -35.97 -77.00 -60.00   95
 24  ω    -63.00  32.00   1.00    1.00    --  -35.97  77.00-180.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1358495000
_diffrn_orient_matrix_UB_12      0.0005503000
_diffrn_orient_matrix_UB_13      0.0660387000
_diffrn_orient_matrix_UB_21      -0.0903609000
_diffrn_orient_matrix_UB_22      0.0302393000
_diffrn_orient_matrix_UB_23      0.0640945000
_diffrn_orient_matrix_UB_31      -0.0233166000
_diffrn_orient_matrix_UB_32      -0.1139027000
_diffrn_orient_matrix_UB_33      0.0173141000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3494
_reflns_number_total             3926
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         2.395
_refine_diff_density_min         -2.094
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3926
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0993
_refine_ls_restrained_S_all      1.129
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1041P)²+5.8922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2526
_refine_ls_wR_factor_ref         0.2595
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.00809(11) 0.89544(9) 0.16423(6) 0.1169(5) Uani 1 1 d . . . . .
O1 O 0.1810(7) 0.5866(5) 0.5150(3) 0.117(2) Uani 1 1 d . . . . .
O2 O 0.3261(4) 0.5450(3) 0.4325(2) 0.0622(10) Uani 1 1 d . . . . .
O3 O 0.1422(4) 0.7523(3) 0.2599(2) 0.0593(9) Uani 1 1 d . . . . .
O4 O -0.2066(5) 0.7632(5) 0.2218(3) 0.1002(17) Uani 1 1 d . . . . .
N1 N -0.1003(4) 0.7325(3) 0.3524(3) 0.0555(11) Uani 1 1 d . . . . .
C1 C 0.3697(5) 0.5535(4) 0.3593(3) 0.0504(11) Uani 1 1 d . . . . .
C2 C 0.4831(6) 0.4906(4) 0.3475(4) 0.0631(15) Uani 1 1 d . . . . .
H2 H 0.5260 0.4462 0.3881 0.076 Uiso 1 1 calc R . . . .
C3 C 0.5294(6) 0.4960(5) 0.2747(4) 0.0694(17) Uani 1 1 d . . . . .
H3 H 0.6037 0.4539 0.2655 0.083 Uiso 1 1 calc R . . . .
C4 C 0.4682(7) 0.5624(6) 0.2152(4) 0.0775(18) Uani 1 1 d . . . . .
H4 H 0.5018 0.5651 0.1663 0.093 Uiso 1 1 calc R . . . .
C5 C 0.3576(7) 0.6251(5) 0.2269(4) 0.0649(14) Uani 1 1 d . . . . .
H5 H 0.3168 0.6700 0.1861 0.078 Uiso 1 1 calc R . . . .
C6 C 0.3063(5) 0.6215(4) 0.3005(3) 0.0474(11) Uani 1 1 d . . . . .
C7 C 0.1930(5) 0.6852(3) 0.3198(3) 0.0432(10) Uani 1 1 d . . . . .
C8 C 0.1479(5) 0.6759(3) 0.3912(3) 0.0447(10) Uani 1 1 d . . . . .
C9 C 0.2150(7) 0.6026(5) 0.4499(4) 0.0638(14) Uani 1 1 d . . . . .
C10 C 0.0316(5) 0.7434(4) 0.4129(3) 0.0518(12) Uani 1 1 d . . . . .
H10 H 0.0128 0.7241 0.4667 0.062 Uiso 1 1 calc R . . . .
C11 C 0.0819(5) 0.8531(4) 0.4149(4) 0.0594(14) Uani 1 1 d . . . . .
C12 C 0.1308(6) 0.9070(6) 0.4853(5) 0.091(3) Uani 1 1 d . . . . .
H12 H 0.1311 0.8776 0.5359 0.110 Uiso 1 1 calc R . . . .
C13 C 0.1808(9) 1.0085(9) 0.4785(9) 0.124(5) Uani 1 1 d . . . . .
H13 H 0.2164 1.0462 0.5248 0.149 Uiso 1 1 calc R . . . .
C14 C 0.1763(10) 1.0490(8) 0.4049(12) 0.148(6) Uani 1 1 d . . . . .
H14 H 0.2061 1.1164 0.4016 0.178 Uiso 1 1 calc R . . . .
C15 C 0.1303(7) 0.9971(5) 0.3340(7) 0.102(3) Uani 1 1 d . . . . .
H15 H 0.1310 1.0281 0.2840 0.122 Uiso 1 1 calc R . . . .
C16 C 0.0826(5) 0.8973(4) 0.3383(4) 0.0618(15) Uani 1 1 d . . . . .
C17 C 0.0326(6) 0.8280(5) 0.2690(4) 0.0671(16) Uani 1 1 d . . . . .
C18 C -0.1054(6) 0.7711(5) 0.2777(4) 0.0619(14) Uani 1 1 d . . . . .
C19 C -0.2135(6) 0.6641(4) 0.3697(5) 0.0681(17) Uani 1 1 d . . . . .
H19A H -0.1702 0.6066 0.4017 0.082 Uiso 1 1 calc R . . . .
H19B H -0.2662 0.6376 0.3189 0.082 Uiso 1 1 calc R . . . .
C20 C -0.3155(5) 0.7170(4) 0.4150(4) 0.0543(13) Uani 1 1 d . . . . .
C21 C -0.4116(6) 0.7892(4) 0.3776(4) 0.0619(14) Uani 1 1 d . . . . .
H21 H -0.4110 0.8076 0.3239 0.074 Uiso 1 1 calc R . . . .
C22 C -0.5080(6) 0.8342(5) 0.4187(4) 0.0694(16) Uani 1 1 d . . . . .
H22 H -0.5730 0.8817 0.3922 0.083 Uiso 1 1 calc R . . . .
C23 C -0.5096(6) 0.8102(5) 0.4976(5) 0.0702(16) Uani 1 1 d . . . . .
H23 H -0.5752 0.8413 0.5249 0.084 Uiso 1 1 calc R . . . .
C24 C -0.4153(7) 0.7407(5) 0.5363(4) 0.0734(17) Uani 1 1 d . . . . .
H24 H -0.4159 0.7246 0.5904 0.088 Uiso 1 1 calc R . . . .
C25 C -0.3184(6) 0.6939(4) 0.4959(4) 0.0677(16) Uani 1 1 d . . . . .
H25 H -0.2543 0.6462 0.5230 0.081 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 C17 1.938(6) . ?
O1 C9 1.207(7) . ?
O2 C1 1.366(7) . ?
O2 C9 1.370(7) . ?
O3 C7 1.353(6) . ?
O3 C17 1.464(7) . ?
O4 C18 1.219(7) . ?
N1 C10 1.469(7) . ?
N1 C18 1.341(8) . ?
N1 C19 1.467(6) . ?
C1 C2 1.397(7) . ?
C1 C6 1.380(7) . ?
C2 C3 1.368(9) . ?
C3 C4 1.368(10) . ?
C4 C5 1.375(9) . ?
C5 C6 1.404(8) . ?
C6 C7 1.443(7) . ?
C7 C8 1.344(7) . ?
C8 C9 1.437(7) . ?
C8 C10 1.510(7) . ?
C10 C11 1.510(7) . ?
C11 C12 1.378(9) . ?
C11 C16 1.407(9) . ?
C12 C13 1.421(15) . ?
C13 C14 1.333(18) . ?
C14 C15 1.367(17) . ?
C15 C16 1.387(8) . ?
C16 C17 1.480(9) . ?
C17 C18 1.537(8) . ?
C19 C20 1.502(8) . ?
C20 C21 1.383(8) . ?
C20 C25 1.391(9) . ?
C21 C22 1.372(9) . ?
C22 C23 1.359(10) . ?
C23 C24 1.356(10) . ?
C24 C25 1.380(10) . ?

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 O2 C9 121.0(4) . . ?
C7 O3 C17 121.8(4) . . ?
C18 N1 C10 119.2(4) . . ?
C18 N1 C19 120.5(5) . . ?
C19 N1 C10 119.3(5) . . ?
O2 C1 C2 116.4(5) . . ?
O2 C1 C6 121.8(4) . . ?
C6 C1 C2 121.8(5) . . ?
C3 C2 C1 118.3(6) . . ?
C4 C3 C2 121.1(5) . . ?
C3 C4 C5 120.7(6) . . ?
C4 C5 C6 120.0(6) . . ?
C1 C6 C5 118.0(5) . . ?
C1 C6 C7 117.4(4) . . ?
C5 C6 C7 124.6(5) . . ?
O3 C7 C6 113.0(4) . . ?
C8 C7 O3 126.0(4) . . ?
C8 C7 C6 121.1(4) . . ?
C7 C8 C9 119.6(4) . . ?
C7 C8 C10 121.7(4) . . ?
C9 C8 C10 118.6(4) . . ?
O1 C9 O2 116.0(5) . . ?
O1 C9 C8 125.0(5) . . ?
O2 C9 C8 119.0(5) . . ?
N1 C10 C8 110.4(4) . . ?
N1 C10 C11 109.6(4) . . ?
C8 C10 C11 108.5(4) . . ?
C12 C11 C10 124.1(7) . . ?
C12 C11 C16 120.7(6) . . ?
C16 C11 C10 115.1(5) . . ?
C11 C12 C13 118.4(9) . . ?
C14 C13 C12 119.3(9) . . ?
C13 C14 C15 123.7(10) . . ?
C14 C15 C16 118.6(10) . . ?
C11 C16 C17 114.0(5) . . ?
C15 C16 C11 119.2(7) . . ?
C15 C16 C17 126.7(7) . . ?
O3 C17 Br1 100.7(4) . . ?
O3 C17 C16 111.1(5) . . ?
O3 C17 C18 108.6(5) . . ?
C16 C17 Br1 113.5(4) . . ?
C16 C17 C18 112.4(5) . . ?
C18 C17 Br1 109.9(4) . . ?
O4 C18 N1 125.0(6) . . ?
O4 C18 C17 122.5(6) . . ?
N1 C18 C17 112.5(5) . . ?
N1 C19 C20 112.4(4) . . ?
C21 C20 C19 121.4(6) . . ?
C21 C20 C25 117.4(5) . . ?
C25 C20 C19 121.2(5) . . ?
C22 C21 C20 120.8(6) . . ?
C23 C22 C21 120.8(6) . . ?
C24 C23 C22 119.8(6) . . ?
C23 C24 C25 120.3(6) . . ?
C24 C25 C20 120.8(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.441
_oxdiff_exptl_absorpt_empirical_full_min 0.735
