# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_Compound_2c_24mb_ar2_alex1_opus
_database_code_depnum_ccdc_archive 'CCDC 2513396'
loop_
_audit_author_name
_audit_author_address
'Manuel Fernandes'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2025-12-04 deposited with the CCDC.	2026-01-28 downloaded from the CCDC.
;
_audit_creation_date             2024-07-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H27 Cl N2 O2'
_chemical_formula_sum            'C30 H27 Cl N2 O2'
_chemical_formula_weight         482.98
_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'
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'
Cl Cl 0.1484 0.1585 '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                   9.8224(3)
_cell_length_b                   10.4896(3)
_cell_length_c                   12.9397(4)
_cell_angle_alpha                107.5160(10)
_cell_angle_beta                 95.1060(10)
_cell_angle_gamma                103.4500(10)
_cell_volume                     1218.22(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      28.39
_cell_measurement_theta_min      2.22
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0995 before and 0.0643 after correction.
The Ratio of minimum to maximum transmission is 0.8733.
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    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             508
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2.00 -2.00 1.00 0.1020
-1.00 0.00 -1.00 0.0540
-1.00 0.00 0.00 0.0790
-1.00 0.00 1.00 0.0760
-1.00 0.00 2.00 0.0640
0.00 1.00 0.00 0.0750
0.00 -1.00 0.00 0.1130
0.00 1.00 -1.00 0.0820
0.00 -1.00 1.00 0.1110
0.00 0.00 -1.00 0.0280
0.00 0.00 1.00 0.0510
0.00 -2.00 1.00 0.1150
1.00 0.00 1.00 0.0300
1.00 0.00 0.00 0.0540
1.00 0.00 -1.00 0.0650
1.00 -2.00 -2.00 0.0850
1.00 -2.00 2.00 0.1010
2.00 -2.00 1.00 0.0980

_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            45607
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.578
_diffrn_reflns_theta_min         2.116
_diffrn_ambient_temperature      173.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5211
_reflns_number_total             6119
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         6119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      1.040
_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)+(0.0393P)²+0.4484P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1015
_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:
 C9(H9A,H9B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C19(H19), C20(H20), C22(H22), C23(H23), C26(H26), C27(H27), C29(H29),
  C30(H30)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl1 Cl 0.62601(4) 0.99176(3) 0.22341(3) 0.03506(10) Uani 1 1 d . . . . .
O1 O 0.38080(10) 0.37384(10) 0.35309(7) 0.0291(2) Uani 1 1 d . . . . .
O2 O 0.85209(11) -0.01666(11) 0.72219(9) 0.0364(2) Uani 1 1 d . . . . .
N1 N 0.47495(11) 0.27063(11) 0.20487(8) 0.0237(2) Uani 1 1 d . . . . .
N2 N 0.68443(11) 0.56221(11) 0.42190(9) 0.0233(2) Uani 1 1 d . . . . .
H2 H 0.6661(17) 0.5844(17) 0.4896(14) 0.034(4) Uiso 1 1 d . . . . .
C1 C 0.48317(13) 0.35468(13) 0.30985(10) 0.0229(2) Uani 1 1 d . . . . .
C2 C 0.64198(13) 0.41370(12) 0.36490(10) 0.0219(2) Uani 1 1 d . . . . .
C3 C 0.71474(13) 0.36202(12) 0.26810(10) 0.0231(2) Uani 1 1 d . . . . .
C4 C 0.85665(14) 0.38609(14) 0.25834(11) 0.0281(3) Uani 1 1 d . . . . .
H4 H 0.928147 0.446088 0.318871 0.034 Uiso 1 1 calc R U . . .
C5 C 0.89305(15) 0.32040(15) 0.15760(12) 0.0336(3) Uani 1 1 d . . . . .
H5 H 0.990236 0.334656 0.149998 0.040 Uiso 1 1 calc R U . . .
C6 C 0.78860(16) 0.23483(15) 0.06892(12) 0.0344(3) Uani 1 1 d . . . . .
H6 H 0.815453 0.190792 0.001321 0.041 Uiso 1 1 calc R U . . .
C7 C 0.64504(15) 0.21196(14) 0.07673(11) 0.0296(3) Uani 1 1 d . . . . .
H7 H 0.573265 0.154862 0.015464 0.036 Uiso 1 1 calc R U . . .
C8 C 0.61138(13) 0.27594(12) 0.17753(10) 0.0231(2) Uani 1 1 d . . . . .
C9 C 0.34113(14) 0.18666(13) 0.13385(11) 0.0282(3) Uani 1 1 d . . . . .
H9A H 0.275351 0.152005 0.179180 0.034 Uiso 1 1 calc R U . . .
H9B H 0.358307 0.104879 0.079864 0.034 Uiso 1 1 calc R U . . .
C10 C 0.26927(14) 0.26152(14) 0.07183(10) 0.0274(3) Uani 1 1 d . . . . .
C11 C 0.30727(17) 0.40413(16) 0.09909(13) 0.0383(3) Uani 1 1 d . . . . .
H11 H 0.382945 0.459259 0.158048 0.046 Uiso 1 1 calc R U . . .
C12 C 0.23573(19) 0.46800(19) 0.04097(15) 0.0472(4) Uani 1 1 d . . . . .
H12 H 0.263379 0.566326 0.060236 0.057 Uiso 1 1 calc R U . . .
C13 C 0.12573(18) 0.3902(2) -0.04380(14) 0.0468(4) Uani 1 1 d . . . . .
H13 H 0.077668 0.433970 -0.083827 0.056 Uiso 1 1 calc R U . . .
C14 C 0.08559(17) 0.2478(2) -0.07037(12) 0.0442(4) Uani 1 1 d . . . . .
H14 H 0.008368 0.193411 -0.128274 0.053 Uiso 1 1 calc R U . . .
C15 C 0.15681(15) 0.18327(17) -0.01341(11) 0.0353(3) Uani 1 1 d . . . . .
H15 H 0.128524 0.084938 -0.032807 0.042 Uiso 1 1 calc R U . . .
C16 C 0.65765(13) 0.33951(13) 0.45032(10) 0.0234(2) Uani 1 1 d . . . . .
H16A H 0.583957 0.351589 0.497050 0.028 Uiso 1 1 calc R U . . .
H16B H 0.638775 0.238791 0.410538 0.028 Uiso 1 1 calc R U . . .
C17 C 0.80277(14) 0.39026(14) 0.52507(11) 0.0280(3) Uani 1 1 d . . . . .
H17A H 0.878621 0.401661 0.480407 0.034 Uiso 1 1 calc R U . . .
H17B H 0.811520 0.482096 0.580097 0.034 Uiso 1 1 calc R U . . .
C18 C 0.82240(13) 0.28937(13) 0.58376(10) 0.0249(2) Uani 1 1 d . . . . .
C19 C 0.72111(14) 0.24096(15) 0.64237(11) 0.0310(3) Uani 1 1 d . . . . .
H19 H 0.641522 0.277764 0.650897 0.037 Uiso 1 1 calc R U . . .
C20 C 0.73498(14) 0.14030(16) 0.68814(12) 0.0320(3) Uani 1 1 d . . . . .
H20 H 0.664928 0.108331 0.727463 0.038 Uiso 1 1 calc R U . . .
C21 C 0.85077(14) 0.08594(14) 0.67682(11) 0.0272(3) Uani 1 1 d . . . . .
C22 C 0.95571(14) 0.13639(14) 0.62385(11) 0.0296(3) Uani 1 1 d . . . . .
H22 H 1.037504 0.102678 0.618732 0.036 Uiso 1 1 calc R U . . .
C23 C 0.93993(14) 0.23762(14) 0.57791(11) 0.0280(3) Uani 1 1 d . . . . .
H23 H 1.012258 0.272206 0.541397 0.034 Uiso 1 1 calc R U . . .
C24 C 0.9631(2) -0.08343(19) 0.70477(16) 0.0484(4) Uani 1 1 d . . . . .
H24A H 0.963547 -0.120653 0.625700 0.073 Uiso 1 1 calc R U . . .
H24B H 0.947333 -0.159515 0.735306 0.073 Uiso 1 1 calc R U . . .
H24C H 1.054694 -0.015984 0.741329 0.073 Uiso 1 1 calc R U . . .
C25 C 0.66575(12) 0.65901(12) 0.37178(10) 0.0219(2) Uani 1 1 d . . . . .
C26 C 0.67378(13) 0.79393(13) 0.43926(10) 0.0251(2) Uani 1 1 d . . . . .
H26 H 0.687850 0.815529 0.516861 0.030 Uiso 1 1 calc R U . . .
C27 C 0.66156(14) 0.89643(13) 0.39484(11) 0.0275(3) Uani 1 1 d . . . . .
H27 H 0.667882 0.987707 0.441454 0.033 Uiso 1 1 calc R U . . .
C28 C 0.63998(13) 0.86408(13) 0.28151(11) 0.0257(3) Uani 1 1 d . . . . .
C29 C 0.63121(14) 0.73241(13) 0.21322(11) 0.0271(3) Uani 1 1 d . . . . .
H29 H 0.615957 0.711438 0.135682 0.033 Uiso 1 1 calc R U . . .
C30 C 0.64473(14) 0.63031(13) 0.25800(10) 0.0257(3) Uani 1 1 d . . . . .
H30 H 0.639629 0.539732 0.210659 0.031 Uiso 1 1 calc R U . . .


_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
Cl1 C28 1.7468(12) . ?
O1 C1 1.2210(15) . ?
O2 C21 1.3743(15) . ?
O2 C24 1.4262(19) . ?
N1 C1 1.3622(16) . ?
N1 C8 1.4091(16) . ?
N1 C9 1.4516(16) . ?
N2 H2 0.882(17) . ?
N2 C2 1.4478(15) . ?
N2 C25 1.3953(15) . ?
C1 C2 1.5529(17) . ?
C2 C3 1.5181(16) . ?
C2 C16 1.5473(16) . ?
C3 C4 1.3818(18) . ?
C3 C8 1.3943(17) . ?
C4 H4 0.9500 . ?
C4 C5 1.3996(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.392(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.3835(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5150(17) . ?
C10 C11 1.379(2) . ?
C10 C15 1.3881(19) . ?
C11 H11 0.9500 . ?
C11 C12 1.392(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.370(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.377(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(2) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5306(17) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.5121(16) . ?
C18 C19 1.3978(18) . ?
C18 C23 1.3840(18) . ?
C19 H19 0.9500 . ?
C19 C20 1.3832(18) . ?
C20 H20 0.9500 . ?
C20 C21 1.3862(18) . ?
C21 C22 1.3793(18) . ?
C22 H22 0.9500 . ?
C22 C23 1.3947(18) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.4013(17) . ?
C25 C30 1.3968(17) . ?
C26 H26 0.9500 . ?
C26 C27 1.3858(17) . ?
C27 H27 0.9500 . ?
C27 C28 1.3864(18) . ?
C28 C29 1.3756(18) . ?
C29 H29 0.9500 . ?
C29 C30 1.3880(17) . ?
C30 H30 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 O2 C24 117.48(11) . . ?
C1 N1 C8 110.99(10) . . ?
C1 N1 C9 122.95(11) . . ?
C8 N1 C9 126.06(10) . . ?
C2 N2 H2 112.7(11) . . ?
C25 N2 H2 112.1(11) . . ?
C25 N2 C2 123.32(10) . . ?
O1 C1 N1 124.64(12) . . ?
O1 C1 C2 126.76(11) . . ?
N1 C1 C2 108.52(10) . . ?
N2 C2 C1 114.01(10) . . ?
N2 C2 C3 116.18(10) . . ?
N2 C2 C16 108.48(10) . . ?
C3 C2 C1 101.23(10) . . ?
C3 C2 C16 111.74(10) . . ?
C16 C2 C1 104.55(9) . . ?
C4 C3 C2 131.47(12) . . ?
C4 C3 C8 119.68(11) . . ?
C8 C3 C2 108.84(10) . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.74(13) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.56(13) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.38(12) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 121.4 . . ?
C8 C7 C6 117.15(13) . . ?
C8 C7 H7 121.4 . . ?
C3 C8 N1 109.95(10) . . ?
C7 C8 N1 127.56(12) . . ?
C7 C8 C3 122.46(12) . . ?
N1 C9 H9A 108.6 . . ?
N1 C9 H9B 108.6 . . ?
N1 C9 C10 114.79(10) . . ?
H9A C9 H9B 107.5 . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C11 C10 C9 122.82(12) . . ?
C11 C10 C15 118.69(13) . . ?
C15 C10 C9 118.44(12) . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.56(15) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.51(16) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.29(14) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.60(15) . . ?
C15 C14 H14 119.7 . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.34(15) . . ?
C14 C15 H15 119.8 . . ?
C2 C16 H16A 108.5 . . ?
C2 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C17 C16 C2 115.22(10) . . ?
C17 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
C16 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 C16 111.45(10) . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C19 C18 C17 121.72(11) . . ?
C23 C18 C17 120.79(11) . . ?
C23 C18 C19 117.45(11) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.02(12) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.21(12) . . ?
C21 C20 H20 119.9 . . ?
O2 C21 C20 115.59(11) . . ?
O2 C21 C22 124.40(12) . . ?
C22 C21 C20 120.01(12) . . ?
C21 C22 H22 120.5 . . ?
C21 C22 C23 119.01(12) . . ?
C23 C22 H22 120.5 . . ?
C18 C23 C22 122.18(12) . . ?
C18 C23 H23 118.9 . . ?
C22 C23 H23 118.9 . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N2 C25 C26 118.28(11) . . ?
N2 C25 C30 123.58(11) . . ?
C30 C25 C26 118.10(11) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 C25 121.19(11) . . ?
C27 C26 H26 119.4 . . ?
C26 C27 H27 120.4 . . ?
C26 C27 C28 119.17(12) . . ?
C28 C27 H27 120.4 . . ?
C27 C28 Cl1 120.10(10) . . ?
C29 C28 Cl1 118.97(10) . . ?
C29 C28 C27 120.93(11) . . ?
C28 C29 H29 120.1 . . ?
C28 C29 C30 119.76(12) . . ?
C30 C29 H29 120.1 . . ?
C25 C30 H30 119.6 . . ?
C29 C30 C25 120.85(11) . . ?
C29 C30 H30 119.6 . . ?

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
Cl1 C28 C29 C30 178.80(10) . . . . ?
O1 C1 C2 N2 -50.66(16) . . . . ?
O1 C1 C2 C3 -176.16(12) . . . . ?
O1 C1 C2 C16 67.63(15) . . . . ?
O2 C21 C22 C23 177.87(13) . . . . ?
N1 C1 C2 N2 132.36(10) . . . . ?
N1 C1 C2 C3 6.86(12) . . . . ?
N1 C1 C2 C16 -109.34(10) . . . . ?
N1 C9 C10 C11 -15.07(19) . . . . ?
N1 C9 C10 C15 167.45(12) . . . . ?
N2 C2 C3 C4 50.66(17) . . . . ?
N2 C2 C3 C8 -129.52(11) . . . . ?
N2 C2 C16 C17 -52.14(14) . . . . ?
N2 C25 C26 C27 177.53(11) . . . . ?
N2 C25 C30 C29 -177.97(11) . . . . ?
C1 N1 C8 C3 2.31(13) . . . . ?
C1 N1 C8 C7 -175.57(12) . . . . ?
C1 N1 C9 C10 85.30(14) . . . . ?
C1 C2 C3 C4 174.70(12) . . . . ?
C1 C2 C3 C8 -5.48(12) . . . . ?
C1 C2 C16 C17 -174.13(10) . . . . ?
C2 N2 C25 C26 162.86(11) . . . . ?
C2 N2 C25 C30 -19.62(18) . . . . ?
C2 C3 C4 C5 178.43(12) . . . . ?
C2 C3 C8 N1 2.44(13) . . . . ?
C2 C3 C8 C7 -179.56(11) . . . . ?
C2 C16 C17 C18 -164.83(10) . . . . ?
C3 C2 C16 C17 77.20(13) . . . . ?
C3 C4 C5 C6 1.09(19) . . . . ?
C4 C3 C8 N1 -177.72(11) . . . . ?
C4 C3 C8 C7 0.28(18) . . . . ?
C4 C5 C6 C7 0.3(2) . . . . ?
C5 C6 C7 C8 -1.4(2) . . . . ?
C6 C7 C8 N1 178.72(12) . . . . ?
C6 C7 C8 C3 1.09(18) . . . . ?
C8 N1 C1 O1 177.01(11) . . . . ?
C8 N1 C1 C2 -5.93(13) . . . . ?
C8 N1 C9 C10 -95.72(14) . . . . ?
C8 C3 C4 C5 -1.37(18) . . . . ?
C9 N1 C1 O1 -3.88(18) . . . . ?
C9 N1 C1 C2 173.18(10) . . . . ?
C9 N1 C8 C3 -176.77(11) . . . . ?
C9 N1 C8 C7 5.36(19) . . . . ?
C9 C10 C11 C12 -178.56(14) . . . . ?
C9 C10 C15 C14 178.25(13) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C11 C10 C15 C14 0.7(2) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C13 C14 C15 -1.0(2) . . . . ?
C13 C14 C15 C10 0.4(2) . . . . ?
C15 C10 C11 C12 -1.1(2) . . . . ?
C16 C2 C3 C4 -74.52(16) . . . . ?
C16 C2 C3 C8 105.30(11) . . . . ?
C16 C17 C18 C19 -51.30(17) . . . . ?
C16 C17 C18 C23 126.37(13) . . . . ?
C17 C18 C19 C20 174.74(13) . . . . ?
C17 C18 C23 C22 -174.91(12) . . . . ?
C18 C19 C20 C21 0.3(2) . . . . ?
C19 C18 C23 C22 2.9(2) . . . . ?
C19 C20 C21 O2 -177.94(13) . . . . ?
C19 C20 C21 C22 2.8(2) . . . . ?
C20 C21 C22 C23 -2.9(2) . . . . ?
C21 C22 C23 C18 0.1(2) . . . . ?
C23 C18 C19 C20 -3.0(2) . . . . ?
C24 O2 C21 C20 175.03(14) . . . . ?
C24 O2 C21 C22 -5.7(2) . . . . ?
C25 N2 C2 C1 -55.32(15) . . . . ?
C25 N2 C2 C3 61.84(15) . . . . ?
C25 N2 C2 C16 -171.34(10) . . . . ?
C25 C26 C27 C28 0.47(19) . . . . ?
C26 C25 C30 C29 -0.45(18) . . . . ?
C26 C27 C28 Cl1 -179.35(10) . . . . ?
C26 C27 C28 C29 -0.3(2) . . . . ?
C27 C28 C29 C30 -0.3(2) . . . . ?
C28 C29 C30 C25 0.7(2) . . . . ?
C30 C25 C26 C27 -0.12(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
####################################################################### 
# 
# 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_Compound_3e_21mbb_mbrack_mandyamp_k4_0f
_database_code_depnum_ccdc_archive 'CCDC 2513397'
loop_
_audit_author_name
_audit_author_address
'Manuel Fernandes'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2025-12-04 deposited with the CCDC.	2026-01-28 downloaded from the CCDC.
;
_audit_creation_date             2023-11-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H29 Br N2 O4'
_chemical_formula_sum            'C28 H29 Br N2 O4'
_chemical_formula_weight         537.44
_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/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                   14.1456(18)
_cell_length_b                   17.8889(19)
_cell_length_c                   10.4103(13)
_cell_angle_alpha                90
_cell_angle_beta                 103.055(4)
_cell_angle_gamma                90
_cell_volume                     2566.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5904
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      25.95
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   0.920
_shelx_estimated_absorpt_T_min   0.508
_exptl_absorpt_coefficient_mu    1.638
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1621 before and 0.1053 after correction.
The Ratio of minimum to maximum transmission is 0.7756.
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    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1112
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 -1.00 0.1900
0.00 -1.00 0.00 0.0670
0.00 1.00 0.00 0.0170
-1.00 -1.00 0.00 0.0800
1.00 1.00 0.00 0.0080
-1.00 0.00 0.00 0.0560
1.00 0.00 0.00 0.0170
1.00 -1.00 0.00 0.0260
-1.00 1.00 0.00 0.0210
0.00 0.00 1.00 0.2200

_exptl_crystal_size_max          0.478
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1113
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            44998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         2.277
_diffrn_ambient_temperature      173.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4098
_reflns_number_total             5591
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         5591
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.034
_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)+(0.0230P)²+1.7451P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0900
_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:
 C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C16(H16), C17(H17),
 C24(H24), C25(H25), C27(H27), C28(H28)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.05919(2) 0.43216(2) 0.34554(3) 0.03891(10) Uani 1 1 d . . . . .
O1 O 0.75340(13) 0.63423(10) 0.15736(17) 0.0326(4) Uani 1 1 d . . . . .
O2 O 0.75000(15) 0.71450(11) 0.3234(2) 0.0484(6) Uani 1 1 d . . . . .
O3 O 0.55046(13) 0.59408(9) 0.03757(17) 0.0282(4) Uani 1 1 d . . . . .
O4 O 0.85474(15) 0.18649(9) 0.42238(19) 0.0401(5) Uani 1 1 d . . . . .
N1 N 0.62591(15) 0.63315(10) 0.25040(19) 0.0238(4) Uani 1 1 d . . . . .
N2 N 0.43307(15) 0.50115(11) 0.1727(2) 0.0263(5) Uani 1 1 d . . . . .
C1 C 0.71419(19) 0.66516(13) 0.2495(3) 0.0291(6) Uani 1 1 d . . . . .
C2 C 0.56798(18) 0.65590(12) 0.3370(2) 0.0244(5) Uani 1 1 d . . . . .
C3 C 0.58032(19) 0.71742(13) 0.4220(3) 0.0295(6) Uani 1 1 d . . . . .
H3A H 0.633218 0.750867 0.427238 0.035 Uiso 1 1 calc R U . . .
C4 C 0.5135(2) 0.72796(14) 0.4979(3) 0.0319(6) Uani 1 1 d . . . . .
H4 H 0.520358 0.769983 0.555070 0.038 Uiso 1 1 calc R U . . .
C5 C 0.4360(2) 0.67932(14) 0.4940(3) 0.0311(6) Uani 1 1 d . . . . .
H5 H 0.392484 0.687262 0.550113 0.037 Uiso 1 1 calc R U . . .
C6 C 0.42288(19) 0.61940(13) 0.4079(2) 0.0277(6) Uani 1 1 d . . . . .
H6 H 0.370034 0.586030 0.403884 0.033 Uiso 1 1 calc R U . . .
C7 C 0.48796(18) 0.60844(12) 0.3272(2) 0.0237(5) Uani 1 1 d . . . . .
C8 C 0.49031(18) 0.55389(12) 0.2233(2) 0.0237(5) Uani 1 1 d . . . . .
C9 C 0.58070(18) 0.56884(13) 0.1678(2) 0.0241(5) Uani 1 1 d . . . . .
C10 C 0.64442(18) 0.49896(13) 0.1793(2) 0.0254(5) Uani 1 1 d . . . . .
H10A H 0.605961 0.457584 0.130096 0.030 Uiso 1 1 calc R U . . .
H10B H 0.699540 0.509042 0.137696 0.030 Uiso 1 1 calc R U . . .
C11 C 0.6837(2) 0.47456(14) 0.3210(3) 0.0319(6) Uani 1 1 d . . . . .
H11A H 0.729688 0.513190 0.365675 0.038 Uiso 1 1 calc R U . . .
H11B H 0.629088 0.472884 0.365852 0.038 Uiso 1 1 calc R U . . .
C12 C 0.73488(19) 0.39960(13) 0.3397(2) 0.0263(5) Uani 1 1 d . . . . .
C13 C 0.7060(2) 0.33868(14) 0.2566(3) 0.0313(6) Uani 1 1 d . . . . .
H13 H 0.656712 0.345110 0.178578 0.038 Uiso 1 1 calc R U . . .
C14 C 0.7478(2) 0.26891(14) 0.2858(3) 0.0333(6) Uani 1 1 d . . . . .
H14 H 0.727391 0.228225 0.227519 0.040 Uiso 1 1 calc R U . . .
C15 C 0.81899(19) 0.25809(13) 0.3992(3) 0.0307(6) Uani 1 1 d . . . . .
C16 C 0.8497(2) 0.31772(15) 0.4812(3) 0.0415(7) Uani 1 1 d . . . . .
H16 H 0.899218 0.311152 0.558908 0.050 Uiso 1 1 calc R U . . .
C17 C 0.8083(2) 0.38746(14) 0.4500(3) 0.0389(7) Uani 1 1 d . . . . .
H17 H 0.831270 0.428407 0.506605 0.047 Uiso 1 1 calc R U . . .
C18 C 0.9079(2) 0.16998(16) 0.5528(3) 0.0432(7) Uani 1 1 d . . . . .
H18A H 0.920795 0.116158 0.560982 0.065 Uiso 1 1 calc R U . . .
H18B H 0.869953 0.185167 0.616373 0.065 Uiso 1 1 calc R U . . .
H18C H 0.969588 0.197283 0.570768 0.065 Uiso 1 1 calc R U . . .
C19 C 0.85776(19) 0.64462(15) 0.1619(3) 0.0325(6) Uani 1 1 d . . . . .
C20 C 0.8801(2) 0.72553(16) 0.1363(3) 0.0461(8) Uani 1 1 d . . . . .
H20A H 0.838448 0.741844 0.052508 0.069 Uiso 1 1 calc R U . . .
H20B H 0.948307 0.730049 0.131770 0.069 Uiso 1 1 calc R U . . .
H20C H 0.867921 0.756935 0.207969 0.069 Uiso 1 1 calc R U . . .
C21 C 0.9158(2) 0.61759(18) 0.2932(3) 0.0517(8) Uani 1 1 d . . . . .
H21A H 0.904492 0.650768 0.363197 0.078 Uiso 1 1 calc R U . . .
H21B H 0.984934 0.617726 0.292651 0.078 Uiso 1 1 calc R U . . .
H21C H 0.895568 0.566683 0.309326 0.078 Uiso 1 1 calc R U . . .
C22 C 0.8721(2) 0.59381(19) 0.0520(4) 0.0552(9) Uani 1 1 d . . . . .
H22A H 0.854869 0.542485 0.070513 0.083 Uiso 1 1 calc R U . . .
H22B H 0.940149 0.595504 0.045810 0.083 Uiso 1 1 calc R U . . .
H22C H 0.830515 0.610463 -0.031553 0.083 Uiso 1 1 calc R U . . .
C23 C 0.34640(18) 0.48724(13) 0.2163(2) 0.0260(5) Uani 1 1 d . . . . .
C24 C 0.26612(19) 0.53344(13) 0.1790(2) 0.0276(6) Uani 1 1 d . . . . .
H24 H 0.269460 0.576191 0.126016 0.033 Uiso 1 1 calc R U . . .
C25 C 0.18147(19) 0.51762(13) 0.2183(2) 0.0294(6) Uani 1 1 d . . . . .
H25 H 0.126739 0.549536 0.193152 0.035 Uiso 1 1 calc R U . . .
C26 C 0.17676(19) 0.45502(14) 0.2945(2) 0.0297(6) Uani 1 1 d . . . . .
C27 C 0.2556(2) 0.40819(14) 0.3318(3) 0.0347(6) Uani 1 1 d . . . . .
H27 H 0.251714 0.365241 0.384033 0.042 Uiso 1 1 calc R U . . .
C28 C 0.34062(19) 0.42439(14) 0.2923(3) 0.0338(6) Uani 1 1 d . . . . .
H28 H 0.395183 0.392290 0.317293 0.041 Uiso 1 1 calc R U . . .
H3 H 0.562(2) 0.5633(16) -0.016(3) 0.041(9) Uiso 1 1 d . . . . .


_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 C26 1.901(3) . ?
O1 C1 1.332(3) . ?
O1 C19 1.478(3) . ?
O2 C1 1.205(3) . ?
O3 C9 1.401(3) . ?
O3 H3 0.82(3) . ?
O4 C15 1.378(3) . ?
O4 C18 1.427(3) . ?
N1 C1 1.376(3) . ?
N1 C2 1.408(3) . ?
N1 C9 1.491(3) . ?
N2 C8 1.277(3) . ?
N2 C23 1.423(3) . ?
C2 C3 1.399(3) . ?
C2 C7 1.400(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.375(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.393(3) . ?
C7 C8 1.463(3) . ?
C8 C9 1.541(3) . ?
C9 C10 1.530(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.518(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.515(3) . ?
C12 C13 1.394(3) . ?
C12 C17 1.381(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(4) . ?
C15 C16 1.374(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.385(4) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.518(4) . ?
C19 C21 1.506(4) . ?
C19 C22 1.510(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.387(3) . ?
C23 C28 1.387(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.380(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.383(4) . ?
C26 C27 1.379(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.387(4) . ?
C28 H28 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
C1 O1 C19 120.00(19) . . ?
C9 O3 H3 112(2) . . ?
C15 O4 C18 116.9(2) . . ?
C1 N1 C2 123.0(2) . . ?
C1 N1 C9 126.1(2) . . ?
C2 N1 C9 110.88(19) . . ?
C8 N2 C23 120.6(2) . . ?
O1 C1 N1 111.0(2) . . ?
O2 C1 O1 125.5(3) . . ?
O2 C1 N1 123.5(2) . . ?
C3 C2 N1 128.7(2) . . ?
C3 C2 C7 120.4(2) . . ?
C7 C2 N1 110.9(2) . . ?
C2 C3 H3A 121.1 . . ?
C4 C3 C2 117.9(2) . . ?
C4 C3 H3A 121.1 . . ?
C3 C4 H4 118.8 . . ?
C3 C4 C5 122.4(2) . . ?
C5 C4 H4 118.8 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 120.3 . . ?
C5 C6 C7 119.3(2) . . ?
C7 C6 H6 120.3 . . ?
C2 C7 C8 107.8(2) . . ?
C6 C7 C2 120.3(2) . . ?
C6 C7 C8 131.9(2) . . ?
N2 C8 C7 132.8(2) . . ?
N2 C8 C9 118.4(2) . . ?
C7 C8 C9 108.7(2) . . ?
O3 C9 N1 107.88(18) . . ?
O3 C9 C8 108.73(19) . . ?
O3 C9 C10 112.63(19) . . ?
N1 C9 C8 101.62(18) . . ?
N1 C9 C10 114.64(19) . . ?
C10 C9 C8 110.67(19) . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 C9 113.0(2) . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C10 C11 H11A 108.3 . . ?
C10 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C12 C11 C10 116.0(2) . . ?
C12 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
C13 C12 C11 123.2(2) . . ?
C17 C12 C11 119.6(2) . . ?
C17 C12 C13 117.0(2) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.1(2) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.5(2) . . ?
C15 C14 H14 119.8 . . ?
O4 C15 C14 116.6(2) . . ?
C16 C15 O4 124.1(2) . . ?
C16 C15 C14 119.3(2) . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.7(2) . . ?
C17 C16 H16 120.1 . . ?
C12 C17 C16 122.4(2) . . ?
C12 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 C19 C20 111.1(2) . . ?
O1 C19 C21 108.9(2) . . ?
O1 C19 C22 101.8(2) . . ?
C21 C19 C20 111.9(2) . . ?
C21 C19 C22 110.8(3) . . ?
C22 C19 C20 111.8(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 N2 121.1(2) . . ?
C24 C23 C28 119.5(2) . . ?
C28 C23 N2 119.3(2) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.3(2) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 H25 120.2 . . ?
C24 C25 C26 119.6(2) . . ?
C26 C25 H25 120.2 . . ?
C25 C26 Br1 119.5(2) . . ?
C27 C26 Br1 119.6(2) . . ?
C27 C26 C25 120.8(3) . . ?
C26 C27 H27 120.3 . . ?
C26 C27 C28 119.3(2) . . ?
C28 C27 H27 120.3 . . ?
C23 C28 H28 119.8 . . ?
C27 C28 C23 120.3(2) . . ?
C27 C28 H28 119.8 . . ?

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 C26 C27 C28 178.8(2) . . . . ?
O3 C9 C10 C11 175.7(2) . . . . ?
O4 C15 C16 C17 -179.2(3) . . . . ?
N1 C2 C3 C4 -179.9(2) . . . . ?
N1 C2 C7 C6 177.7(2) . . . . ?
N1 C2 C7 C8 -3.3(3) . . . . ?
N1 C9 C10 C11 51.8(3) . . . . ?
N2 C8 C9 O3 65.9(3) . . . . ?
N2 C8 C9 N1 179.5(2) . . . . ?
N2 C8 C9 C10 -58.4(3) . . . . ?
N2 C23 C24 C25 177.6(2) . . . . ?
N2 C23 C28 C27 -177.6(2) . . . . ?
C1 O1 C19 C20 -67.2(3) . . . . ?
C1 O1 C19 C21 56.5(3) . . . . ?
C1 O1 C19 C22 173.6(2) . . . . ?
C1 N1 C2 C3 8.6(4) . . . . ?
C1 N1 C2 C7 -173.1(2) . . . . ?
C1 N1 C9 O3 -71.6(3) . . . . ?
C1 N1 C9 C8 174.1(2) . . . . ?
C1 N1 C9 C10 54.7(3) . . . . ?
C2 N1 C1 O1 -179.1(2) . . . . ?
C2 N1 C1 O2 1.0(4) . . . . ?
C2 N1 C9 O3 111.2(2) . . . . ?
C2 N1 C9 C8 -3.0(2) . . . . ?
C2 N1 C9 C10 -122.4(2) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C2 C7 C8 N2 -176.9(3) . . . . ?
C2 C7 C8 C9 1.3(3) . . . . ?
C3 C2 C7 C6 -3.9(4) . . . . ?
C3 C2 C7 C8 175.1(2) . . . . ?
C3 C4 C5 C6 -2.3(4) . . . . ?
C4 C5 C6 C7 0.5(4) . . . . ?
C5 C6 C7 C2 2.5(4) . . . . ?
C5 C6 C7 C8 -176.2(2) . . . . ?
C6 C7 C8 N2 2.0(5) . . . . ?
C6 C7 C8 C9 -179.9(2) . . . . ?
C7 C2 C3 C4 2.1(4) . . . . ?
C7 C8 C9 O3 -112.6(2) . . . . ?
C7 C8 C9 N1 1.0(2) . . . . ?
C7 C8 C9 C10 123.2(2) . . . . ?
C8 N2 C23 C24 75.5(3) . . . . ?
C8 N2 C23 C28 -107.7(3) . . . . ?
C8 C9 C10 C11 -62.4(3) . . . . ?
C9 N1 C1 O1 4.1(3) . . . . ?
C9 N1 C1 O2 -175.8(2) . . . . ?
C9 N1 C2 C3 -174.1(2) . . . . ?
C9 N1 C2 C7 4.1(3) . . . . ?
C9 C10 C11 C12 171.2(2) . . . . ?
C10 C11 C12 C13 -35.8(4) . . . . ?
C10 C11 C12 C17 150.3(3) . . . . ?
C11 C12 C13 C14 -172.6(3) . . . . ?
C11 C12 C17 C16 171.9(3) . . . . ?
C12 C13 C14 C15 0.5(4) . . . . ?
C13 C12 C17 C16 -2.4(5) . . . . ?
C13 C14 C15 O4 178.3(3) . . . . ?
C13 C14 C15 C16 -1.7(4) . . . . ?
C14 C15 C16 C17 0.8(5) . . . . ?
C15 C16 C17 C12 1.3(5) . . . . ?
C17 C12 C13 C14 1.5(4) . . . . ?
C18 O4 C15 C14 -163.8(3) . . . . ?
C18 O4 C15 C16 16.2(4) . . . . ?
C19 O1 C1 O2 16.5(4) . . . . ?
C19 O1 C1 N1 -163.3(2) . . . . ?
C23 N2 C8 C7 0.8(4) . . . . ?
C23 N2 C8 C9 -177.2(2) . . . . ?
C23 C24 C25 C26 -0.5(4) . . . . ?
C24 C23 C28 C27 -0.7(4) . . . . ?
C24 C25 C26 Br1 -178.69(19) . . . . ?
C24 C25 C26 C27 0.0(4) . . . . ?
C25 C26 C27 C28 0.1(4) . . . . ?
C26 C27 C28 C23 0.2(4) . . . . ?
C28 C23 C24 C25 0.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
