# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc2myjjn
_database_code_depnum_ccdc_archive 'CCDC 2441452'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2025-nqq2t 2025
loop_
_audit_author_name
_audit_author_address
'Dr. Shobhana Krishnaswamy'
;IIT Madras
India
;
_audit_update_record             
;
2025-04-07 deposited with the CCDC.	2025-12-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H22 Cl N O'
_chemical_formula_weight         495.97

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   9.314(2)
_cell_length_b                   24.125(6)
_cell_length_c                   11.578(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.692(6)
_cell_angle_gamma                90
_cell_volume                     2598.7(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5366
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      22.41

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.596
_exptl_crystal_size_mid          0.520
_exptl_crystal_size_min          0.406
_exptl_absorpt_coefficient_mu    0.175
_shelx_estimated_absorpt_T_min   0.903
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8641
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector 
scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37790
_diffrn_reflns_av_unetI/netI     0.0808
_diffrn_reflns_av_R_equivalents  0.0955
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.346
_diffrn_reflns_theta_max         25.264
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             4593
_reflns_number_gt                2253
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019), WinGX'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0258P)²+4.0287P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0034(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4593
_refine_ls_number_parameters     375
_refine_ls_number_restraints     86
_refine_ls_R_factor_all          0.1665
_refine_ls_R_factor_gt           0.0756
_refine_ls_wR_factor_ref         0.1824
_refine_ls_wR_factor_gt          0.1537
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 1.2195(3) 0.29580(9) 0.6754(2) 0.1051(10) Uani 0.775(4) 1 d D U P A 1
C1 C 1.1086(6) 0.2955(2) 0.5528(4) 0.069(2) Uani 0.775(4) 1 d DG U P A 1
C2 C 1.0848(7) 0.24618(17) 0.4930(5) 0.101(3) Uani 0.775(4) 1 d G U P A 1
H2 H 1.128909 0.213700 0.519408 0.121 Uiso 0.775(4) 1 calc R U P A 1
C3 C 0.9949(8) 0.24539(19) 0.3937(5) 0.105(3) Uani 0.775(4) 1 d G U P A 1
H3 H 0.978914 0.212373 0.353686 0.126 Uiso 0.775(4) 1 calc R U P A 1
C4 C 0.9289(6) 0.2939(2) 0.3543(4) 0.094(2) Uani 0.775(4) 1 d G U P A 1
H4 H 0.868756 0.293408 0.287835 0.113 Uiso 0.775(4) 1 calc R U P A 1
C5 C 0.9528(7) 0.34329(19) 0.4141(5) 0.074(3) Uani 0.775(4) 1 d G U P A 1
H5 H 0.908593 0.375771 0.387705 0.089 Uiso 0.775(4) 1 calc R U P A 1
C6 C 1.0426(7) 0.34408(17) 0.5134(5) 0.057(2) Uani 0.775(4) 1 d DG U P A 1
Cl1' Cl 0.9121(14) 0.3616(5) 0.3693(8) 0.124(4) Uani 0.225(4) 1 d D U P A 2
C1' C 1.007(3) 0.3170(8) 0.4506(19) 0.096(8) Uani 0.225(4) 1 d DG U P A 2
C2' C 1.000(3) 0.2614(10) 0.4189(19) 0.123(9) Uani 0.225(4) 1 d G U P A 2
H2' H 0.951321 0.251049 0.350315 0.148 Uiso 0.225(4) 1 calc R U P A 2
C3' C 1.065(3) 0.2214(6) 0.490(2) 0.146(10) Uani 0.225(4) 1 d G U P A 2
H3' H 1.060575 0.184240 0.468749 0.175 Uiso 0.225(4) 1 calc R U P A 2
C4' C 1.138(3) 0.2369(8) 0.5925(19) 0.137(9) Uani 0.225(4) 1 d G U P A 2
H4' H 1.181701 0.210148 0.639955 0.165 Uiso 0.225(4) 1 calc R U P A 2
C5' C 1.145(3) 0.2925(9) 0.6241(17) 0.115(9) Uani 0.225(4) 1 d G U P A 2
H5' H 1.193572 0.302865 0.692729 0.138 Uiso 0.225(4) 1 calc R U P A 2
C6' C 1.080(3) 0.3325(6) 0.553(2) 0.087(8) Uani 0.225(4) 1 d DG U P A 2
C7 C 1.0706(5) 0.39632(18) 0.5798(4) 0.0533(12) Uani 1 1 d D . . . .
C8 C 1.1593(5) 0.4367(2) 0.5324(4) 0.0717(15) Uani 1 1 d . . . . .
H8 H 1.203966 0.428919 0.464049 0.086 Uiso 1 1 calc R U . . .
C9 C 1.1815(6) 0.4865(2) 0.5833(5) 0.0768(16) Uani 1 1 d . . . . .
H9 H 1.243221 0.512002 0.551664 0.092 Uiso 1 1 calc R U . . .
C10 C 1.1129(6) 0.4991(2) 0.6813(5) 0.0756(16) Uani 1 1 d . . . . .
H10 H 1.127108 0.533581 0.715881 0.091 Uiso 1 1 calc R U . . .
C11 C 1.0235(5) 0.46151(19) 0.7291(4) 0.0644(13) Uani 1 1 d . . . . .
H11 H 0.977482 0.470913 0.795922 0.077 Uiso 1 1 calc R U . . .
C12 C 0.9999(4) 0.40971(18) 0.6803(4) 0.0486(11) Uani 1 1 d . . . . .
C13 C 0.8896(4) 0.36952(17) 0.7260(3) 0.0474(11) Uani 1 1 d . . . . .
H13 H 0.923311 0.331416 0.716151 0.057 Uiso 1 1 calc R U . . .
C14 C 0.8537(5) 0.37840(18) 0.8505(4) 0.0542(12) Uani 1 1 d . . . . .
C15 C 0.9354(6) 0.3749(2) 0.9514(4) 0.0770(16) Uani 1 1 d . . . . .
H15 H 1.031708 0.364704 0.951256 0.092 Uiso 1 1 calc R U . . .
C16 C 0.8695(7) 0.3870(3) 1.0559(4) 0.098(2) Uani 1 1 d . . . . .
H16 H 0.923766 0.383671 1.125090 0.118 Uiso 1 1 calc R U . . .
C17 C 0.7297(7) 0.4035(3) 1.0597(5) 0.098(2) Uani 1 1 d . . . . .
H17 H 0.691607 0.412104 1.130328 0.117 Uiso 1 1 calc R U . . .
C18 C 0.6428(6) 0.4077(2) 0.9576(4) 0.0715(15) Uani 1 1 d . . . . .
C19 C 0.4967(7) 0.4231(3) 0.9446(5) 0.0932(19) Uani 1 1 d . . . . .
H19 H 0.447444 0.433251 1.009442 0.112 Uiso 1 1 calc R U . . .
C20 C 0.4274(6) 0.4234(2) 0.8395(6) 0.0867(18) Uani 1 1 d . . . . .
H20 H 0.330729 0.433272 0.834528 0.104 Uiso 1 1 calc R U . . .
C21 C 0.4942(5) 0.40959(19) 0.7376(4) 0.0641(13) Uani 1 1 d . . . . .
H21 H 0.443439 0.410030 0.666479 0.077 Uiso 1 1 calc R U . . .
C22 C 0.6362(5) 0.39542(17) 0.7460(4) 0.0481(11) Uani 1 1 d . . . . .
C23 C 0.7092(5) 0.39444(18) 0.8544(4) 0.0549(12) Uani 1 1 d . . . . .
C24 C 0.7414(4) 0.37748(16) 0.6557(3) 0.0464(11) Uani 1 1 d . . . . .
H24 H 0.750317 0.406851 0.598001 0.056 Uiso 1 1 calc R U . . .
C25 C 0.6853(5) 0.32502(19) 0.5974(4) 0.0538(12) Uani 1 1 d . . . . .
C26 C 0.5819(5) 0.33128(18) 0.4960(4) 0.0512(11) Uani 1 1 d . . . . .
C27 C 0.5106(6) 0.28423(19) 0.4493(4) 0.0709(15) Uani 1 1 d . . . . .
H27 H 0.529317 0.249174 0.479867 0.085 Uiso 1 1 calc R U . . .
C28 C 0.4142(6) 0.2911(2) 0.3590(4) 0.0746(15) Uani 1 1 d . . . . .
H28 H 0.366370 0.260515 0.327062 0.089 Uiso 1 1 calc R U . . .
C29 C 0.3863(5) 0.34394(19) 0.3136(4) 0.0561(12) Uani 1 1 d . . . . .
C30 C 0.2845(5) 0.3546(2) 0.2223(4) 0.0711(15) Uani 1 1 d . . . . .
H30 H 0.233193 0.325463 0.187548 0.085 Uiso 1 1 calc R U . . .
C31 C 0.2615(5) 0.4073(2) 0.1853(4) 0.0688(14) Uani 1 1 d . . . . .
H31 H 0.192899 0.414161 0.126069 0.083 Uiso 1 1 calc R U . . .
C32 C 0.3398(5) 0.4514(2) 0.2350(4) 0.0615(13) Uani 1 1 d . . . . .
H32 H 0.322994 0.487178 0.207864 0.074 Uiso 1 1 calc R U . . .
C33 C 0.4392(5) 0.44290(19) 0.3216(4) 0.0553(12) Uani 1 1 d . . . . .
H33 H 0.490956 0.472652 0.353137 0.066 Uiso 1 1 calc R U . . .
C34 C 0.4647(4) 0.38854(17) 0.3646(3) 0.0467(11) Uani 1 1 d . . . . .
N1 N 0.5614(4) 0.38182(14) 0.4557(3) 0.0488(9) Uani 1 1 d . . . . .
O1 O 0.7181(4) 0.27892(13) 0.6351(3) 0.0783(11) Uani 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
Cl1 C1 1.715(4) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C2 H2 0.9300 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 C7 1.493(6) . ?
Cl1' C1' 1.657(14) . ?
C1' C2' 1.3900 . ?
C1' C6' 1.3900 . ?
C2' C3' 1.3900 . ?
C2' H2' 0.9300 . ?
C3' C4' 1.3900 . ?
C3' H3' 0.9300 . ?
C4' C5' 1.3900 . ?
C4' H4' 0.9300 . ?
C5' C6' 1.3900 . ?
C5' H5' 0.9300 . ?
C6' C7 1.573(13) . ?
C7 C12 1.402(6) . ?
C7 C8 1.406(6) . ?
C8 C9 1.349(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.362(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.366(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.385(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.525(6) . ?
C13 C14 1.510(6) . ?
C13 C24 1.581(5) . ?
C13 H13 0.9800 . ?
C14 C15 1.366(6) . ?
C14 C23 1.403(6) . ?
C15 C16 1.413(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.365(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.404(7) . ?
C17 H17 0.9300 . ?
C18 C23 1.408(6) . ?
C18 C19 1.412(7) . ?
C19 C20 1.351(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.399(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.366(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.399(6) . ?
C22 C24 1.528(6) . ?
C24 C25 1.515(6) . ?
C24 H24 0.9800 . ?
C25 O1 1.228(5) . ?
C25 C26 1.491(6) . ?
C26 N1 1.316(5) . ?
C26 C27 1.410(6) . ?
C27 C28 1.356(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.398(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.410(6) . ?
C29 C34 1.414(6) . ?
C30 C31 1.355(7) . ?
C30 H30 0.9300 . ?
C31 C32 1.399(6) . ?
C31 H31 0.9300 . ?
C32 C33 1.348(6) . ?
C32 H32 0.9300 . ?
C33 C34 1.419(6) . ?
C33 H33 0.9300 . ?
C34 N1 1.364(5) . ?

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
C2 C1 C6 120.0 . . ?
C2 C1 Cl1 119.4(3) . . ?
C6 C1 Cl1 120.6(3) . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 C7 121.4(4) . . ?
C1 C6 C7 118.6(4) . . ?
C2' C1' C6' 120.0 . . ?
C2' C1' Cl1' 117.4(17) . . ?
C6' C1' Cl1' 122.3(17) . . ?
C1' C2' C3' 120.0 . . ?
C1' C2' H2' 120.0 . . ?
C3' C2' H2' 120.0 . . ?
C2' C3' C4' 120.0 . . ?
C2' C3' H3' 120.0 . . ?
C4' C3' H3' 120.0 . . ?
C5' C4' C3' 120.0 . . ?
C5' C4' H4' 120.0 . . ?
C3' C4' H4' 120.0 . . ?
C4' C5' C6' 120.0 . . ?
C4' C5' H5' 120.0 . . ?
C6' C5' H5' 120.0 . . ?
C5' C6' C1' 120.0 . . ?
C5' C6' C7 126.1(16) . . ?
C1' C6' C7 113.8(16) . . ?
C12 C7 C8 118.2(4) . . ?
C12 C7 C6 123.0(5) . . ?
C8 C7 C6 118.4(5) . . ?
C12 C7 C6' 114.8(11) . . ?
C8 C7 C6' 124.3(11) . . ?
C9 C8 C7 121.8(5) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 119.7(5) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 120.5(5) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 121.5(5) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C7 118.4(4) . . ?
C11 C12 C13 121.9(4) . . ?
C7 C12 C13 119.5(4) . . ?
C14 C13 C12 115.1(4) . . ?
C14 C13 C24 104.3(3) . . ?
C12 C13 C24 109.3(3) . . ?
C14 C13 H13 109.3 . . ?
C12 C13 H13 109.3 . . ?
C24 C13 H13 109.3 . . ?
C15 C14 C23 119.1(4) . . ?
C15 C14 C13 131.9(4) . . ?
C23 C14 C13 109.0(4) . . ?
C14 C15 C16 118.2(5) . . ?
C14 C15 H15 120.9 . . ?
C16 C15 H15 120.9 . . ?
C17 C16 C15 122.8(5) . . ?
C17 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
C16 C17 C18 120.5(5) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C23 116.0(5) . . ?
C17 C18 C19 128.5(5) . . ?
C23 C18 C19 115.5(5) . . ?
C20 C19 C18 120.9(5) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 123.1(5) . . ?
C19 C20 H20 118.5 . . ?
C21 C20 H20 118.5 . . ?
C22 C21 C20 117.9(5) . . ?
C22 C21 H21 121.1 . . ?
C20 C21 H21 121.1 . . ?
C21 C22 C23 119.8(4) . . ?
C21 C22 C24 132.2(4) . . ?
C23 C22 C24 108.0(4) . . ?
C22 C23 C14 113.7(4) . . ?
C22 C23 C18 122.9(4) . . ?
C14 C23 C18 123.4(4) . . ?
C25 C24 C22 108.8(3) . . ?
C25 C24 C13 113.7(3) . . ?
C22 C24 C13 104.7(3) . . ?
C25 C24 H24 109.8 . . ?
C22 C24 H24 109.8 . . ?
C13 C24 H24 109.8 . . ?
O1 C25 C26 120.8(4) . . ?
O1 C25 C24 121.6(4) . . ?
C26 C25 C24 117.5(4) . . ?
N1 C26 C27 123.5(4) . . ?
N1 C26 C25 116.8(4) . . ?
C27 C26 C25 119.7(4) . . ?
C28 C27 C26 118.7(5) . . ?
C28 C27 H27 120.7 . . ?
C26 C27 H27 120.7 . . ?
C27 C28 C29 120.4(4) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C28 C29 C30 123.6(4) . . ?
C28 C29 C34 117.0(4) . . ?
C30 C29 C34 119.4(4) . . ?
C31 C30 C29 119.9(5) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C30 C31 C32 120.8(5) . . ?
C30 C31 H31 119.6 . . ?
C32 C31 H31 119.6 . . ?
C33 C32 C31 121.2(5) . . ?
C33 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
C32 C33 C34 119.9(4) . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
N1 C34 C29 122.8(4) . . ?
N1 C34 C33 118.3(4) . . ?
C29 C34 C33 118.8(4) . . ?
C26 N1 C34 117.6(4) . . ?

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
C6 C1 C2 C3 0.0 . . . . ?
Cl1 C1 C2 C3 179.8(4) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C4 C5 C6 C7 -180.0(6) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
Cl1 C1 C6 C5 -179.8(5) . . . . ?
C2 C1 C6 C7 180.0(6) . . . . ?
Cl1 C1 C6 C7 0.1(6) . . . . ?
C6' C1' C2' C3' 0.0 . . . . ?
Cl1' C1' C2' C3' -173.6(19) . . . . ?
C1' C2' C3' C4' 0.0 . . . . ?
C2' C3' C4' C5' 0.0 . . . . ?
C3' C4' C5' C6' 0.0 . . . . ?
C4' C5' C6' C1' 0.0 . . . . ?
C4' C5' C6' C7 176(2) . . . . ?
C2' C1' C6' C5' 0.0 . . . . ?
Cl1' C1' C6' C5' 173(2) . . . . ?
C2' C1' C6' C7 -177(2) . . . . ?
Cl1' C1' C6' C7 -4(2) . . . . ?
C5 C6 C7 C12 99.5(5) . . . . ?
C1 C6 C7 C12 -80.5(6) . . . . ?
C5 C6 C7 C8 -73.0(6) . . . . ?
C1 C6 C7 C8 107.0(5) . . . . ?
C5' C6' C7 C12 -59.9(19) . . . . ?
C1' C6' C7 C12 116.7(14) . . . . ?
C5' C6' C7 C8 101.2(15) . . . . ?
C1' C6' C7 C8 -82.2(17) . . . . ?
C12 C7 C8 C9 2.5(7) . . . . ?
C6 C7 C8 C9 175.3(5) . . . . ?
C6' C7 C8 C9 -158.0(12) . . . . ?
C7 C8 C9 C10 -2.2(8) . . . . ?
C8 C9 C10 C11 0.9(8) . . . . ?
C9 C10 C11 C12 0.1(8) . . . . ?
C10 C11 C12 C7 0.2(7) . . . . ?
C10 C11 C12 C13 -174.0(4) . . . . ?
C8 C7 C12 C11 -1.4(6) . . . . ?
C6 C7 C12 C11 -173.9(4) . . . . ?
C6' C7 C12 C11 160.9(12) . . . . ?
C8 C7 C12 C13 172.9(4) . . . . ?
C6 C7 C12 C13 0.4(6) . . . . ?
C6' C7 C12 C13 -24.7(12) . . . . ?
C11 C12 C13 C14 -23.8(6) . . . . ?
C7 C12 C13 C14 162.1(4) . . . . ?
C11 C12 C13 C24 93.2(5) . . . . ?
C7 C12 C13 C24 -81.0(5) . . . . ?
C12 C13 C14 C15 -63.2(7) . . . . ?
C24 C13 C14 C15 177.1(5) . . . . ?
C12 C13 C14 C23 114.9(4) . . . . ?
C24 C13 C14 C23 -4.8(5) . . . . ?
C23 C14 C15 C16 0.7(8) . . . . ?
C13 C14 C15 C16 178.6(5) . . . . ?
C14 C15 C16 C17 -1.8(10) . . . . ?
C15 C16 C17 C18 1.8(11) . . . . ?
C16 C17 C18 C23 -0.5(9) . . . . ?
C16 C17 C18 C19 179.0(6) . . . . ?
C17 C18 C19 C20 -178.0(6) . . . . ?
C23 C18 C19 C20 1.6(9) . . . . ?
C18 C19 C20 C21 -1.0(10) . . . . ?
C19 C20 C21 C22 -0.3(8) . . . . ?
C20 C21 C22 C23 0.8(7) . . . . ?
C20 C21 C22 C24 178.9(5) . . . . ?
C21 C22 C23 C14 179.1(4) . . . . ?
C24 C22 C23 C14 0.6(5) . . . . ?
C21 C22 C23 C18 -0.2(7) . . . . ?
C24 C22 C23 C18 -178.7(4) . . . . ?
C15 C14 C23 C22 -178.8(4) . . . . ?
C13 C14 C23 C22 2.8(5) . . . . ?
C15 C14 C23 C18 0.5(7) . . . . ?
C13 C14 C23 C18 -177.9(4) . . . . ?
C17 C18 C23 C22 178.6(5) . . . . ?
C19 C18 C23 C22 -1.0(7) . . . . ?
C17 C18 C23 C14 -0.6(8) . . . . ?
C19 C18 C23 C14 179.8(5) . . . . ?
C21 C22 C24 C25 -59.8(6) . . . . ?
C23 C22 C24 C25 118.4(4) . . . . ?
C21 C22 C24 C13 178.2(5) . . . . ?
C23 C22 C24 C13 -3.5(4) . . . . ?
C14 C13 C24 C25 -113.7(4) . . . . ?
C12 C13 C24 C25 122.7(4) . . . . ?
C14 C13 C24 C22 5.0(4) . . . . ?
C12 C13 C24 C22 -118.6(4) . . . . ?
C22 C24 C25 O1 -90.1(5) . . . . ?
C13 C24 C25 O1 26.1(6) . . . . ?
C22 C24 C25 C26 86.6(4) . . . . ?
C13 C24 C25 C26 -157.1(4) . . . . ?
O1 C25 C26 N1 -174.8(4) . . . . ?
C24 C25 C26 N1 8.5(6) . . . . ?
O1 C25 C26 C27 6.0(7) . . . . ?
C24 C25 C26 C27 -170.8(4) . . . . ?
N1 C26 C27 C28 -0.9(8) . . . . ?
C25 C26 C27 C28 178.3(4) . . . . ?
C26 C27 C28 C29 -0.1(8) . . . . ?
C27 C28 C29 C30 -178.0(5) . . . . ?
C27 C28 C29 C34 1.2(7) . . . . ?
C28 C29 C30 C31 178.4(5) . . . . ?
C34 C29 C30 C31 -0.8(7) . . . . ?
C29 C30 C31 C32 1.3(8) . . . . ?
C30 C31 C32 C33 -0.6(8) . . . . ?
C31 C32 C33 C34 -0.7(7) . . . . ?
C28 C29 C34 N1 -1.4(7) . . . . ?
C30 C29 C34 N1 177.8(4) . . . . ?
C28 C29 C34 C33 -179.7(4) . . . . ?
C30 C29 C34 C33 -0.4(6) . . . . ?
C32 C33 C34 N1 -177.1(4) . . . . ?
C32 C33 C34 C29 1.2(6) . . . . ?
C27 C26 N1 C34 0.7(7) . . . . ?
C25 C26 N1 C34 -178.5(4) . . . . ?
C29 C34 N1 C26 0.5(6) . . . . ?
C33 C34 N1 C26 178.7(4) . . . . ?

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_shelx_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc2n1g6d
_database_code_depnum_ccdc_archive 'CCDC 2444263'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2025-nqq2t 2025
loop_
_audit_author_name
_audit_author_address
'Dr. Shobhana Krishnaswamy'
;IIT Madras
India
;
_audit_update_record             
;
2025-04-16 deposited with the CCDC.	2025-12-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 Br Cl O'
_chemical_formula_weight         487.80

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8017(10)
_cell_length_b                   10.1659(9)
_cell_length_c                   11.4676(12)
_cell_angle_alpha                81.365(3)
_cell_angle_beta                 84.820(4)
_cell_angle_gamma                86.723(3)
_cell_volume                     1124.00(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9931
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      25.01

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.965
_shelx_estimated_absorpt_T_min   0.724
_shelx_estimated_absorpt_T_max   0.784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5656
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   
;
 SADABS-2016/2 - Bruker AXS area detector 
 scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture Diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50460
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.510
_diffrn_reflns_theta_max         25.038
_diffrn_reflns_theta_full        25.038
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3966
_reflns_number_gt                2994
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX4 (Bruker, 2021)'
_computing_cell_refinement       'APEX4/SAINT (Bruker, 2021)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019), WinGX'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0407P)²+1.4068P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3966
_refine_ls_number_parameters     320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1198
_refine_ls_wR_factor_gt          0.1071
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.9355(4) 0.8033(3) 0.3289(3) 0.0441(8) Uani 1 1 d . . . . .
C2 C 0.7997(4) 0.7752(4) 0.3297(4) 0.0539(10) Uani 1 1 d . . . . .
H2 H 0.732621 0.843766 0.322842 0.065 Uiso 1 1 calc R U . . .
C3 C 0.7643(3) 0.6443(3) 0.3407(4) 0.0502(10) Uani 1 1 d . . . . .
H3 H 0.672604 0.625023 0.341292 0.060 Uiso 1 1 calc R U . . .
C4 C 0.8637(3) 0.5402(3) 0.3511(3) 0.0399(8) Uani 1 1 d . . . . .
C5 C 0.9996(3) 0.5716(3) 0.3489(3) 0.0463(9) Uani 1 1 d . . . . .
H5 H 1.067451 0.503750 0.354572 0.056 Uiso 1 1 calc R U . . .
C6 C 1.0356(4) 0.7023(4) 0.3384(4) 0.0505(9) Uani 1 1 d . . . . .
H6 H 1.127150 0.722220 0.337834 0.061 Uiso 1 1 calc R U . . .
C7 C 0.8317(3) 0.3963(3) 0.3620(3) 0.0424(8) Uani 1 1 d . . . . .
C8 C 0.6826(3) 0.3561(3) 0.3903(3) 0.0369(8) Uani 1 1 d . . . . .
H8 H 0.620456 0.424425 0.351370 0.044 Uiso 1 1 calc R U . . .
C9 C 0.6480(3) 0.3372(3) 0.5237(3) 0.0378(8) Uani 1 1 d . . . . .
C10 C 0.6341(3) 0.4332(4) 0.5991(3) 0.0434(9) Uani 1 1 d . . . . .
H10 H 0.643769 0.522892 0.569781 0.052 Uiso 1 1 calc R U . . .
C11 C 0.6056(4) 0.3916(5) 0.7191(4) 0.0560(11) Uani 1 1 d . . . . .
H11 H 0.596252 0.454478 0.770722 0.067 Uiso 1 1 calc R U . . .
C12 C 0.5909(4) 0.2591(5) 0.7635(4) 0.0577(11) Uani 1 1 d . . . . .
H12 H 0.571028 0.233554 0.844354 0.069 Uiso 1 1 calc R U . . .
C13 C 0.6056(4) 0.1634(4) 0.6879(3) 0.0516(10) Uani 1 1 d . . . . .
H13 H 0.595314 0.073898 0.717454 0.062 Uiso 1 1 calc R U . . .
C14 C 0.6357(3) 0.2033(3) 0.5679(3) 0.0389(8) Uani 1 1 d . . . . .
C15 C 0.6631(4) 0.1178(3) 0.4705(3) 0.0433(8) Uani 1 1 d . . . . .
H15A H 0.593322 0.052772 0.475585 0.052 Uiso 1 1 calc R U . . .
H15B H 0.752203 0.071435 0.474893 0.052 Uiso 1 1 calc R U . . .
C16 C 0.6586(3) 0.2180(3) 0.3548(3) 0.0391(8) Uani 1 1 d . . . . .
H16 H 0.733706 0.195120 0.297939 0.047 Uiso 1 1 calc R U . . .
C17 C 0.5232(3) 0.2224(3) 0.2983(3) 0.0410(8) Uani 1 1 d . . . . .
C18 C 0.5209(4) 0.2351(5) 0.1755(4) 0.0629(11) Uani 1 1 d . . . . .
C19 C 0.3948(5) 0.2427(6) 0.1274(5) 0.0859(16) Uani 1 1 d . . . . .
H19 H 0.392627 0.250585 0.045699 0.103 Uiso 1 1 calc R U . . .
C20 C 0.2727(5) 0.2387(5) 0.1981(5) 0.0757(14) Uani 1 1 d . . . . .
H20 H 0.189693 0.243789 0.163896 0.091 Uiso 1 1 calc R U . . .
C21 C 0.2741(4) 0.2274(4) 0.3175(5) 0.0603(11) Uani 1 1 d . . . . .
H21 H 0.192225 0.225658 0.365394 0.072 Uiso 1 1 calc R U . . .
C22 C 0.3982(4) 0.2184(3) 0.3674(4) 0.0490(9) Uani 1 1 d . . . . .
H22 H 0.398477 0.209439 0.449274 0.059 Uiso 1 1 calc R U . . .
C23 C 0.6552(6) 0.2732(8) 0.0943(6) 0.060(2) Uani 0.592(5) 1 d G . P A 1
C24 C 0.7328(7) 0.1673(7) 0.0549(6) 0.071(2) Uani 0.592(5) 1 d G . P A 1
C25 C 0.8572(8) 0.1897(9) -0.0116(7) 0.093(5) Uani 0.592(5) 1 d G . P A 1
H25 H 0.909054 0.118867 -0.037980 0.111 Uiso 0.592(5) 1 calc R U P A 1
C26 C 0.9040(7) 0.3181(11) -0.0387(7) 0.105(4) Uani 0.592(5) 1 d G . P A 1
H26 H 0.987255 0.333166 -0.083198 0.126 Uiso 0.592(5) 1 calc R U P A 1
C27 C 0.8265(9) 0.4241(8) 0.0007(8) 0.122(4) Uani 0.592(5) 1 d G . P A 1
H27 H 0.857813 0.509970 -0.017445 0.146 Uiso 0.592(5) 1 calc R U P A 1
C28 C 0.7021(9) 0.4016(7) 0.0672(8) 0.092(5) Uani 0.592(5) 1 d G . P A 1
H28 H 0.650170 0.472477 0.093527 0.111 Uiso 0.592(5) 1 calc R U P A 1
Cl1 Cl 0.6780(5) 0.0107(4) 0.0832(4) 0.1069(14) Uani 0.592(5) 1 d . . P A 1
C23' C 0.6457(8) 0.1970(10) 0.1003(8) 0.055(3) Uani 0.408(5) 1 d G . P A 2
C24' C 0.7345(11) 0.2987(8) 0.0590(8) 0.073(4) Uani 0.408(5) 1 d G . P A 2
C25' C 0.8538(11) 0.2733(12) -0.0107(11) 0.088(6) Uani 0.408(5) 1 d G . P A 2
H25' H 0.913165 0.341305 -0.038270 0.106 Uiso 0.408(5) 1 calc R U P A 2
C26' C 0.8843(10) 0.1461(14) -0.0391(10) 0.107(8) Uani 0.408(5) 1 d G . P A 2
H26' H 0.964088 0.129055 -0.085773 0.128 Uiso 0.408(5) 1 calc R U P A 2
C27' C 0.7955(12) 0.0444(10) 0.0021(10) 0.092(4) Uani 0.408(5) 1 d G . P A 2
H27' H 0.815889 -0.040716 -0.016930 0.110 Uiso 0.408(5) 1 calc R U P A 2
C28' C 0.6762(11) 0.0698(9) 0.0718(10) 0.082(6) Uani 0.408(5) 1 d G . P A 2
H28' H 0.616766 0.001762 0.099418 0.099 Uiso 0.408(5) 1 calc R U P A 2
Cl1' Cl 0.6911(7) 0.4576(5) 0.0880(5) 0.0956(18) Uani 0.408(5) 1 d . . P A 2
O1 O 0.9230(3) 0.3123(3) 0.3525(3) 0.0659(8) Uani 1 1 d . . . . .
Br1 Br 0.98694(4) 0.98182(4) 0.31348(5) 0.06793(19) Uani 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
C1 C2 1.375(5) . ?
C1 C6 1.379(5) . ?
C1 Br1 1.890(3) . ?
C2 C3 1.380(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.396(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(5) . ?
C4 C7 1.498(5) . ?
C5 C6 1.379(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.211(4) . ?
C7 C8 1.533(4) . ?
C8 C9 1.522(5) . ?
C8 C16 1.555(4) . ?
C8 H8 0.9800 . ?
C9 C14 1.388(5) . ?
C9 C10 1.392(5) . ?
C10 C11 1.385(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.391(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.385(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.512(5) . ?
C15 C16 1.549(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.524(5) . ?
C16 H16 0.9800 . ?
C17 C22 1.397(5) . ?
C17 C18 1.397(6) . ?
C18 C19 1.392(6) . ?
C18 C23' 1.499(8) . ?
C18 C23 1.575(7) . ?
C19 C20 1.383(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.358(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.383(5) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.3900 . ?
C23 C28 1.3900 . ?
C24 C25 1.3900 . ?
C24 Cl1 1.684(7) . ?
C25 C26 1.3900 . ?
C25 H25 0.9300 . ?
C26 C27 1.3900 . ?
C26 H26 0.9300 . ?
C27 C28 1.3900 . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C23' C24' 1.3900 . ?
C23' C28' 1.3900 . ?
C24' C25' 1.3900 . ?
C24' Cl1' 1.719(9) . ?
C25' C26' 1.3900 . ?
C25' H25' 0.9300 . ?
C26' C27' 1.3900 . ?
C26' H26' 0.9300 . ?
C27' C28' 1.3900 . ?
C27' H27' 0.9300 . ?
C28' H28' 0.9300 . ?

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
C2 C1 C6 120.7(3) . . ?
C2 C1 Br1 120.1(3) . . ?
C6 C1 Br1 119.1(3) . . ?
C1 C2 C3 119.3(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 118.3(3) . . ?
C5 C4 C7 118.1(3) . . ?
C3 C4 C7 123.6(3) . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C1 C6 C5 119.7(3) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
O1 C7 C4 120.4(3) . . ?
O1 C7 C8 120.3(3) . . ?
C4 C7 C8 119.2(3) . . ?
C9 C8 C7 109.6(3) . . ?
C9 C8 C16 104.0(3) . . ?
C7 C8 C16 112.5(3) . . ?
C9 C8 H8 110.2 . . ?
C7 C8 H8 110.2 . . ?
C16 C8 H8 110.2 . . ?
C14 C9 C10 120.8(3) . . ?
C14 C9 C8 110.7(3) . . ?
C10 C9 C8 128.5(3) . . ?
C11 C10 C9 118.2(4) . . ?
C11 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
C12 C11 C10 121.4(4) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 120.2(4) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 119.1(4) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C9 120.3(3) . . ?
C13 C14 C15 128.5(3) . . ?
C9 C14 C15 111.1(3) . . ?
C14 C15 C16 104.3(3) . . ?
C14 C15 H15A 110.9 . . ?
C16 C15 H15A 110.9 . . ?
C14 C15 H15B 110.9 . . ?
C16 C15 H15B 110.9 . . ?
H15A C15 H15B 108.9 . . ?
C17 C16 C15 113.4(3) . . ?
C17 C16 C8 110.1(3) . . ?
C15 C16 C8 105.5(3) . . ?
C17 C16 H16 109.2 . . ?
C15 C16 H16 109.2 . . ?
C8 C16 H16 109.2 . . ?
C22 C17 C18 118.2(3) . . ?
C22 C17 C16 121.0(3) . . ?
C18 C17 C16 120.7(3) . . ?
C19 C18 C17 118.8(4) . . ?
C19 C18 C23' 117.9(5) . . ?
C17 C18 C23' 120.3(5) . . ?
C19 C18 C23 120.4(5) . . ?
C17 C18 C23 119.3(4) . . ?
C20 C19 C18 121.6(5) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C21 C20 C19 119.9(4) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 119.5(4) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C21 C22 C17 121.9(4) . . ?
C21 C22 H22 119.0 . . ?
C17 C22 H22 119.0 . . ?
C24 C23 C28 120.0 . . ?
C24 C23 C18 115.7(5) . . ?
C28 C23 C18 124.2(5) . . ?
C25 C24 C23 120.0 . . ?
C25 C24 Cl1 118.5(5) . . ?
C23 C24 Cl1 121.5(5) . . ?
C24 C25 C26 120.0 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C27 C26 C25 120.0 . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C28 C27 C26 120.0 . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C23 120.0 . . ?
C27 C28 H28 120.0 . . ?
C23 C28 H28 120.0 . . ?
C24' C23' C28' 120.0 . . ?
C24' C23' C18 115.5(7) . . ?
C28' C23' C18 124.5(7) . . ?
C25' C24' C23' 120.0 . . ?
C25' C24' Cl1' 120.3(7) . . ?
C23' C24' Cl1' 119.6(7) . . ?
C24' C25' C26' 120.0 . . ?
C24' C25' H25' 120.0 . . ?
C26' C25' H25' 120.0 . . ?
C27' C26' C25' 120.0 . . ?
C27' C26' H26' 120.0 . . ?
C25' C26' H26' 120.0 . . ?
C26' C27' C28' 120.0 . . ?
C26' C27' H27' 120.0 . . ?
C28' C27' H27' 120.0 . . ?
C27' C28' C23' 120.0 . . ?
C27' C28' H28' 120.0 . . ?
C23' C28' H28' 120.0 . . ?

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
C6 C1 C2 C3 0.3(6) . . . . ?
Br1 C1 C2 C3 179.9(3) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
C2 C3 C4 C5 -0.6(6) . . . . ?
C2 C3 C4 C7 -179.3(4) . . . . ?
C3 C4 C5 C6 0.9(6) . . . . ?
C7 C4 C5 C6 179.6(4) . . . . ?
C2 C1 C6 C5 0.0(6) . . . . ?
Br1 C1 C6 C5 -179.6(3) . . . . ?
C4 C5 C6 C1 -0.6(6) . . . . ?
C5 C4 C7 O1 -10.0(6) . . . . ?
C3 C4 C7 O1 168.7(4) . . . . ?
C5 C4 C7 C8 167.4(3) . . . . ?
C3 C4 C7 C8 -13.9(5) . . . . ?
O1 C7 C8 C9 92.0(4) . . . . ?
C4 C7 C8 C9 -85.4(4) . . . . ?
O1 C7 C8 C16 -23.2(5) . . . . ?
C4 C7 C8 C16 159.4(3) . . . . ?
C7 C8 C9 C14 -108.5(3) . . . . ?
C16 C8 C9 C14 12.0(3) . . . . ?
C7 C8 C9 C10 68.9(4) . . . . ?
C16 C8 C9 C10 -170.6(3) . . . . ?
C14 C9 C10 C11 -1.0(5) . . . . ?
C8 C9 C10 C11 -178.2(3) . . . . ?
C9 C10 C11 C12 -0.1(5) . . . . ?
C10 C11 C12 C13 0.5(6) . . . . ?
C11 C12 C13 C14 0.3(6) . . . . ?
C12 C13 C14 C9 -1.4(5) . . . . ?
C12 C13 C14 C15 176.6(3) . . . . ?
C10 C9 C14 C13 1.8(5) . . . . ?
C8 C9 C14 C13 179.5(3) . . . . ?
C10 C9 C14 C15 -176.6(3) . . . . ?
C8 C9 C14 C15 1.1(4) . . . . ?
C13 C14 C15 C16 168.1(3) . . . . ?
C9 C14 C15 C16 -13.7(4) . . . . ?
C14 C15 C16 C17 -100.2(3) . . . . ?
C14 C15 C16 C8 20.4(3) . . . . ?
C9 C8 C16 C17 103.0(3) . . . . ?
C7 C8 C16 C17 -138.5(3) . . . . ?
C9 C8 C16 C15 -19.7(3) . . . . ?
C7 C8 C16 C15 98.7(3) . . . . ?
C15 C16 C17 C22 41.2(4) . . . . ?
C8 C16 C17 C22 -76.8(4) . . . . ?
C15 C16 C17 C18 -141.0(4) . . . . ?
C8 C16 C17 C18 101.0(4) . . . . ?
C22 C17 C18 C19 -0.3(6) . . . . ?
C16 C17 C18 C19 -178.1(4) . . . . ?
C22 C17 C18 C23' -160.4(6) . . . . ?
C16 C17 C18 C23' 21.7(7) . . . . ?
C22 C17 C18 C23 165.9(5) . . . . ?
C16 C17 C18 C23 -12.0(6) . . . . ?
C17 C18 C19 C20 0.4(8) . . . . ?
C23' C18 C19 C20 161.0(6) . . . . ?
C23 C18 C19 C20 -165.6(6) . . . . ?
C18 C19 C20 C21 0.1(8) . . . . ?
C19 C20 C21 C22 -0.7(7) . . . . ?
C20 C21 C22 C17 0.9(6) . . . . ?
C18 C17 C22 C21 -0.4(5) . . . . ?
C16 C17 C22 C21 177.5(3) . . . . ?
C19 C18 C23 C24 -96.6(6) . . . . ?
C17 C18 C23 C24 97.5(6) . . . . ?
C19 C18 C23 C28 87.3(6) . . . . ?
C17 C18 C23 C28 -78.6(6) . . . . ?
C28 C23 C24 C25 0.0 . . . . ?
C18 C23 C24 C25 -176.3(6) . . . . ?
C28 C23 C24 Cl1 -178.6(6) . . . . ?
C18 C23 C24 Cl1 5.1(8) . . . . ?
C23 C24 C25 C26 0.0 . . . . ?
Cl1 C24 C25 C26 178.7(6) . . . . ?
C24 C25 C26 C27 0.0 . . . . ?
C25 C26 C27 C28 0.0 . . . . ?
C26 C27 C28 C23 0.0 . . . . ?
C24 C23 C28 C27 0.0 . . . . ?
C18 C23 C28 C27 175.9(7) . . . . ?
C19 C18 C23' C24' 108.8(8) . . . . ?
C17 C18 C23' C24' -90.9(8) . . . . ?
C19 C18 C23' C28' -71.8(8) . . . . ?
C17 C18 C23' C28' 88.5(7) . . . . ?
C28' C23' C24' C25' 0.0 . . . . ?
C18 C23' C24' C25' 179.5(8) . . . . ?
C28' C23' C24' Cl1' 176.5(8) . . . . ?
C18 C23' C24' Cl1' -4.0(11) . . . . ?
C23' C24' C25' C26' 0.0 . . . . ?
Cl1' C24' C25' C26' -176.4(8) . . . . ?
C24' C25' C26' C27' 0.0 . . . . ?
C25' C26' C27' C28' 0.0 . . . . ?
C26' C27' C28' C23' 0.0 . . . . ?
C24' C23' C28' C27' 0.0 . . . . ?
C18 C23' C28' C27' -179.4(9) . . . . ?

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.059

