# 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 
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data_0408zjh_0m
_database_code_depnum_ccdc_archive 'CCDC 2168665'
_audit_update_record             
;
2022-04-25 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_audit_creation_date             2021-04-08
_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         'C27 H22 Br Cl2 N O3'
_chemical_formula_sum            'C27 H22 Br Cl2 N O3'
_chemical_formula_weight         559.26
_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'
Cl Cl 0.1484 0.1585 '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                   12.3719(9)
_cell_length_b                   11.0520(9)
_cell_length_c                   18.6624(14)
_cell_angle_alpha                90
_cell_angle_beta                 103.575(2)
_cell_angle_gamma                90
_cell_volume                     2480.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4399
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.564
_cell_measurement_theta_min      2.503
_shelx_estimated_absorpt_T_max   0.928
_shelx_estimated_absorpt_T_min   0.763
_exptl_absorpt_coefficient_mu    1.902
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0716 before and 0.0474 after correction. The Ratio of minimum to maximum transmission is 0.8133. 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    1.498
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18682
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.420
_diffrn_reflns_theta_min         2.158
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  '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                3147
_reflns_number_total             5012
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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         0.385
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5012
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.005
_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)+(0.0333P)²+1.9670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0973
_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 Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C20(H20), C6(H6), C16(H16), C19(H19), C2(H2), C23(H23),
 C18(H18), C17(H17), C27(H27), C26(H26), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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 0.95286(3) 0.77155(4) 0.80916(2) 0.05671(15) Uani 1 1 d . . . . .
Cl2 Cl 0.60242(8) 0.13641(8) 0.74924(5) 0.0506(3) Uani 1 1 d . . . . .
Cl1 Cl 0.48406(9) -0.07932(8) 0.68696(5) 0.0506(3) Uani 1 1 d . . . . .
O1 O 0.28251(16) 0.38419(17) 0.58263(11) 0.0294(5) Uani 1 1 d . . . . .
O2 O 0.74847(17) 0.23997(19) 0.63565(13) 0.0393(6) Uani 1 1 d . . . . .
N1 N 0.62812(19) 0.3954(2) 0.64713(14) 0.0263(6) Uani 1 1 d . . . . .
O3 O 0.2759(2) 0.4762(2) 0.47495(15) 0.0608(8) Uani 1 1 d . . . . .
C4 C 0.7029(2) 0.4808(3) 0.68728(17) 0.0266(7) Uani 1 1 d . . . . .
C8 C 0.6564(3) 0.2841(3) 0.62370(17) 0.0303(7) Uani 1 1 d . . . . .
C14 C 0.3514(2) 0.2930(3) 0.56327(16) 0.0270(7) Uani 1 1 d . . . . .
C15 C 0.2872(2) 0.1878(3) 0.52668(17) 0.0279(7) Uani 1 1 d . . . . .
C11 C 0.4601(2) 0.3109(3) 0.58221(16) 0.0262(7) Uani 1 1 d . . . . .
C12 C 0.5396(3) 0.0935(3) 0.60015(17) 0.0300(7) Uani 1 1 d . . . . .
H12A H 0.483649 0.052640 0.560977 0.036 Uiso 1 1 calc R . . . .
H12B H 0.611333 0.051395 0.603941 0.036 Uiso 1 1 calc R . . . .
C5 C 0.6701(3) 0.6006(3) 0.68966(17) 0.0318(7) Uani 1 1 d . . . . .
H5 H 0.596668 0.623572 0.665315 0.038 Uiso 1 1 calc R . . . .
C9 C 0.5523(2) 0.2251(3) 0.57540(17) 0.0275(7) Uani 1 1 d . . . . .
C7 C 0.5118(2) 0.4264(3) 0.61575(17) 0.0289(7) Uani 1 1 d . . . . .
H7A H 0.505759 0.490241 0.577813 0.035 Uiso 1 1 calc R . . . .
H7B H 0.475451 0.455065 0.654550 0.035 Uiso 1 1 calc R . . . .
C3 C 0.8093(3) 0.4477(3) 0.72601(19) 0.0379(8) Uani 1 1 d . . . . .
H3 H 0.831666 0.365315 0.727587 0.045 Uiso 1 1 calc R . . . .
C22 C 0.1663(2) 0.5547(3) 0.55431(19) 0.0328(8) Uani 1 1 d . . . . .
C20 C 0.2747(3) 0.1683(3) 0.45200(19) 0.0355(8) Uani 1 1 d . . . . .
H20 H 0.308842 0.221716 0.424062 0.043 Uiso 1 1 calc R . . . .
C13 C 0.5055(3) 0.0772(3) 0.67279(17) 0.0318(7) Uani 1 1 d . . . . .
H13 H 0.433200 0.120065 0.668930 0.038 Uiso 1 1 calc R . . . .
C1 C 0.8504(3) 0.6532(3) 0.76162(18) 0.0358(8) Uani 1 1 d . . . . .
C6 C 0.7431(3) 0.6868(3) 0.72711(18) 0.0350(8) Uani 1 1 d . . . . .
H6 H 0.719729 0.768393 0.729082 0.042 Uiso 1 1 calc R . . . .
C21 C 0.2450(3) 0.4709(3) 0.53079(19) 0.0334(8) Uani 1 1 d . . . . .
C10 C 0.5713(3) 0.2227(3) 0.49660(17) 0.0353(8) Uani 1 1 d . . . . .
H10A H 0.584576 0.305221 0.481418 0.053 Uiso 1 1 calc GR . . . .
H10B H 0.505389 0.189365 0.462616 0.053 Uiso 1 1 calc GR . . . .
H10C H 0.636015 0.172100 0.495714 0.053 Uiso 1 1 calc GR . . . .
C16 C 0.2347(3) 0.1093(3) 0.56592(19) 0.0366(8) Uani 1 1 d . . . . .
H16 H 0.240488 0.123184 0.616927 0.044 Uiso 1 1 calc R . . . .
C19 C 0.2122(3) 0.0704(3) 0.4174(2) 0.0419(9) Uani 1 1 d . . . . .
H19 H 0.203172 0.057938 0.365948 0.050 Uiso 1 1 calc R . . . .
C2 C 0.8820(3) 0.5346(3) 0.7620(2) 0.0425(9) Uani 1 1 d . . . . .
H2 H 0.954962 0.511804 0.787441 0.051 Uiso 1 1 calc R . . . .
C23 C 0.1525(3) 0.5544(3) 0.6256(2) 0.0411(9) Uani 1 1 d . . . . .
H23 H 0.193454 0.499158 0.660656 0.049 Uiso 1 1 calc R . . . .
C18 C 0.1636(3) -0.0080(3) 0.4577(2) 0.0460(10) Uani 1 1 d . . . . .
H18 H 0.122704 -0.075759 0.434438 0.055 Uiso 1 1 calc R . . . .
C17 C 0.1744(3) 0.0119(3) 0.5320(2) 0.0448(9) Uani 1 1 d . . . . .
H17 H 0.140174 -0.041696 0.559785 0.054 Uiso 1 1 calc R . . . .
C27 C 0.1059(3) 0.6338(3) 0.5028(2) 0.0492(10) Uani 1 1 d . . . . .
H27 H 0.115889 0.634951 0.453831 0.059 Uiso 1 1 calc R . . . .
C26 C 0.0309(3) 0.7111(3) 0.5234(3) 0.0625(12) Uani 1 1 d . . . . .
H26 H -0.011800 0.764898 0.488086 0.075 Uiso 1 1 calc R . . . .
C24 C 0.0795(4) 0.6343(4) 0.6459(3) 0.0648(13) Uani 1 1 d . . . . .
H24 H 0.071759 0.636386 0.695329 0.078 Uiso 1 1 calc R . . . .
C25 C 0.0177(4) 0.7110(4) 0.5938(3) 0.0667(13) Uani 1 1 d . . . . .
H25 H -0.034597 0.764334 0.607167 0.080 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 C1 1.891(3) . ?
Cl2 C13 1.760(3) . ?
Cl1 C13 1.779(3) . ?
O1 C14 1.420(3) . ?
O1 C21 1.363(4) . ?
O2 C8 1.211(3) . ?
N1 C4 1.408(4) . ?
N1 C8 1.378(4) . ?
N1 C7 1.461(4) . ?
O3 C21 1.193(4) . ?
C4 C5 1.388(4) . ?
C4 C3 1.393(4) . ?
C8 C9 1.533(4) . ?
C14 C15 1.481(4) . ?
C14 C11 1.323(4) . ?
C15 C20 1.383(4) . ?
C15 C16 1.391(4) . ?
C11 C9 1.512(4) . ?
C11 C7 1.498(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C9 1.544(4) . ?
C12 C13 1.522(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(4) . ?
C9 C10 1.543(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C3 H3 0.9500 . ?
C3 C2 1.378(4) . ?
C22 C21 1.483(4) . ?
C22 C23 1.380(5) . ?
C22 C27 1.382(5) . ?
C20 H20 0.9500 . ?
C20 C19 1.397(5) . ?
C13 H13 1.0000 . ?
C1 C6 1.383(5) . ?
C1 C2 1.368(5) . ?
C6 H6 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C16 H16 0.9500 . ?
C16 C17 1.377(5) . ?
C19 H19 0.9500 . ?
C19 C18 1.374(5) . ?
C2 H2 0.9500 . ?
C23 H23 0.9500 . ?
C23 C24 1.379(5) . ?
C18 H18 0.9500 . ?
C18 C17 1.379(5) . ?
C17 H17 0.9500 . ?
C27 H27 0.9500 . ?
C27 C26 1.381(5) . ?
C26 H26 0.9500 . ?
C26 C25 1.363(6) . ?
C24 H24 0.9500 . ?
C24 C25 1.378(6) . ?
C25 H25 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
C21 O1 C14 116.3(2) . . ?
C4 N1 C7 121.3(2) . . ?
C8 N1 C4 125.7(2) . . ?
C8 N1 C7 112.4(2) . . ?
C5 C4 N1 119.7(3) . . ?
C5 C4 C3 118.8(3) . . ?
C3 C4 N1 121.5(3) . . ?
O2 C8 N1 126.8(3) . . ?
O2 C8 C9 124.1(3) . . ?
N1 C8 C9 109.0(2) . . ?
O1 C14 C15 112.7(2) . . ?
C11 C14 O1 117.3(3) . . ?
C11 C14 C15 129.9(3) . . ?
C20 C15 C14 120.6(3) . . ?
C20 C15 C16 118.5(3) . . ?
C16 C15 C14 120.8(3) . . ?
C14 C11 C9 128.6(3) . . ?
C14 C11 C7 123.1(3) . . ?
C7 C11 C9 108.2(2) . . ?
H12A C12 H12B 107.3 . . ?
C9 C12 H12A 108.2 . . ?
C9 C12 H12B 108.2 . . ?
C13 C12 H12A 108.2 . . ?
C13 C12 H12B 108.2 . . ?
C13 C12 C9 116.6(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C8 C9 C12 110.8(3) . . ?
C8 C9 C10 105.8(2) . . ?
C11 C9 C8 103.3(2) . . ?
C11 C9 C12 115.7(2) . . ?
C11 C9 C10 112.2(2) . . ?
C10 C9 C12 108.6(2) . . ?
N1 C7 C11 104.6(2) . . ?
N1 C7 H7A 110.8 . . ?
N1 C7 H7B 110.8 . . ?
C11 C7 H7A 110.8 . . ?
C11 C7 H7B 110.8 . . ?
H7A C7 H7B 108.9 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.0 . . ?
C23 C22 C21 121.5(3) . . ?
C23 C22 C27 120.2(3) . . ?
C27 C22 C21 118.3(3) . . ?
C15 C20 H20 119.8 . . ?
C15 C20 C19 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
Cl2 C13 Cl1 109.77(18) . . ?
Cl2 C13 H13 108.0 . . ?
Cl1 C13 H13 108.0 . . ?
C12 C13 Cl2 113.5(2) . . ?
C12 C13 Cl1 109.3(2) . . ?
C12 C13 H13 108.0 . . ?
C6 C1 Br1 119.8(2) . . ?
C2 C1 Br1 120.1(3) . . ?
C2 C1 C6 120.1(3) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 C5 119.4(3) . . ?
C1 C6 H6 120.3 . . ?
O1 C21 C22 111.5(3) . . ?
O3 C21 O1 122.0(3) . . ?
O3 C21 C22 126.5(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.0(3) . . ?
C17 C16 H16 119.5 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 C20 120.0(3) . . ?
C18 C19 H19 120.0 . . ?
C3 C2 H2 119.6 . . ?
C1 C2 C3 120.8(3) . . ?
C1 C2 H2 119.6 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.1(3) . . ?
C24 C23 H23 120.0 . . ?
C19 C18 H18 120.1 . . ?
C19 C18 C17 119.9(3) . . ?
C17 C18 H18 120.1 . . ?
C16 C17 C18 120.1(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C22 C27 H27 120.4 . . ?
C26 C27 C22 119.1(4) . . ?
C26 C27 H27 120.4 . . ?
C27 C26 H26 119.7 . . ?
C25 C26 C27 120.6(4) . . ?
C25 C26 H26 119.7 . . ?
C23 C24 H24 120.3 . . ?
C25 C24 C23 119.4(4) . . ?
C25 C24 H24 120.3 . . ?
C26 C25 C24 120.5(4) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
