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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_KB187_0m
_database_code_depnum_ccdc_archive 'CCDC 2164031'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2022-04-02 deposited with the CCDC.	2022-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H19 Br O4'
_chemical_formula_sum            'C23 H19 Br O4'
_chemical_formula_weight         439.29

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'

_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                   11.9543(16)
_cell_length_b                   13.1009(16)
_cell_length_c                   12.3965(14)
_cell_angle_alpha                90
_cell_angle_beta                 98.422(3)
_cell_angle_gamma                90
_cell_volume                     1920.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8646
_cell_measurement_theta_min      2.2735
_cell_measurement_theta_max      25.963

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    2.167
_shelx_estimated_absorpt_T_min   0.582
_shelx_estimated_absorpt_T_max   0.659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6119
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29016
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.275
_diffrn_reflns_theta_max         28.317
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             4708
_reflns_number_gt                3349
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0498P)²+0.6776P] 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         4708
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1072
_refine_ls_wR_factor_gt          0.0939
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
Br1 Br 0.18176(2) 0.04598(2) 0.44502(2) 0.06468(13) Uani 1 1 d . . . . .
O1 O 0.13324(14) 0.56088(13) 0.46077(16) 0.0589(5) Uani 1 1 d . . . . .
O2 O 0.18552(12) 0.78904(13) 0.50624(14) 0.0525(4) Uani 1 1 d . . . . .
O3 O 0.49965(11) 0.69432(10) 0.36753(11) 0.0380(3) Uani 1 1 d . . . . .
O4 O 0.46768(19) 1.03205(14) 0.2979(2) 0.0789(6) Uani 1 1 d . . . . .
C1 C 0.18982(17) 0.18930(18) 0.43095(17) 0.0433(5) Uani 1 1 d . . . . .
C2 C 0.09917(18) 0.24787(19) 0.45261(19) 0.0467(5) Uani 1 1 d . . . . .
H2 H 0.033766 0.216788 0.469008 0.056 Uiso 1 1 calc R U . . .
C3 C 0.10712(17) 0.35239(18) 0.44955(18) 0.0434(5) Uani 1 1 d . . . . .
H3 H 0.047155 0.392036 0.465594 0.052 Uiso 1 1 calc R U . . .
C4 C 0.20412(16) 0.40017(17) 0.42266(16) 0.0379(4) Uani 1 1 d . . . . .
C5 C 0.29261(17) 0.33892(17) 0.39783(18) 0.0442(5) Uani 1 1 d . . . . .
H5 H 0.356759 0.369405 0.377809 0.053 Uiso 1 1 calc R U . . .
C6 C 0.28625(19) 0.23410(18) 0.40258(19) 0.0472(5) Uani 1 1 d . . . . .
H6 H 0.345967 0.193925 0.386922 0.057 Uiso 1 1 calc R U . . .
C7 C 0.20785(16) 0.51327(18) 0.42642(17) 0.0392(4) Uani 1 1 d . . . . .
C8 C 0.30342(16) 0.57300(16) 0.38748(17) 0.0371(4) Uani 1 1 d . . . . .
H8A H 0.283480 0.588423 0.310536 0.045 Uiso 1 1 calc R U . . .
H8B H 0.371363 0.531519 0.396314 0.045 Uiso 1 1 calc R U . . .
C9 C 0.32708(14) 0.67294(15) 0.45161(15) 0.0328(4) Uani 1 1 d . . . . .
C10 C 0.21681(17) 0.73558(17) 0.43929(18) 0.0410(5) Uani 1 1 d . . . . .
H10 H 0.169989 0.731054 0.372597 0.049 Uiso 1 1 calc R U . . .
C11 C 0.37797(14) 0.65633(14) 0.57117(15) 0.0319(4) Uani 1 1 d . . . . .
C12 C 0.39799(17) 0.55959(15) 0.61655(17) 0.0379(4) Uani 1 1 d . . . . .
H12 H 0.379208 0.502018 0.573828 0.045 Uiso 1 1 calc R U . . .
C13 C 0.44548(18) 0.54831(16) 0.72443(18) 0.0437(5) Uani 1 1 d . . . . .
H13 H 0.458885 0.483257 0.753496 0.052 Uiso 1 1 calc R U . . .
C14 C 0.47310(17) 0.63252(17) 0.78917(17) 0.0436(5) Uani 1 1 d . . . . .
H14 H 0.503886 0.624557 0.862040 0.052 Uiso 1 1 calc R U . . .
C15 C 0.45479(17) 0.72883(16) 0.74523(18) 0.0417(5) Uani 1 1 d . . . . .
H15 H 0.473927 0.785979 0.788523 0.050 Uiso 1 1 calc R U . . .
C16 C 0.40830(16) 0.74085(15) 0.63751(17) 0.0367(4) Uani 1 1 d . . . . .
H16 H 0.396978 0.806196 0.608657 0.044 Uiso 1 1 calc R U . . .
C17 C 0.40422(15) 0.73986(15) 0.39664(16) 0.0345(4) Uani 1 1 d . . . . .
C18 C 0.40492(17) 0.83907(16) 0.37385(17) 0.0416(5) Uani 1 1 d . . . . .
H18 H 0.349912 0.886355 0.385494 0.050 Uiso 1 1 calc R U . . .
C19 C 0.50594(17) 0.85977(16) 0.32807(16) 0.0390(4) Uani 1 1 d . . . . .
C20 C 0.56114(16) 0.76912(16) 0.32626(16) 0.0383(4) Uani 1 1 d . . . . .
C21 C 0.6668(2) 0.7332(2) 0.2902(2) 0.0594(7) Uani 1 1 d . . . . .
H21A H 0.654471 0.723222 0.212653 0.089 Uiso 1 1 calc R U . . .
H21B H 0.689551 0.669872 0.325746 0.089 Uiso 1 1 calc R U . . .
H21C H 0.725159 0.783243 0.308787 0.089 Uiso 1 1 calc R U . . .
C22 C 0.5337(2) 0.96262(18) 0.2923(2) 0.0501(5) Uani 1 1 d . . . . .
C23 C 0.6407(2) 0.9800(2) 0.2451(3) 0.0709(8) Uani 1 1 d . . . . .
H23A H 0.640248 0.938415 0.181276 0.106 Uiso 1 1 calc R U . . .
H23B H 0.704519 0.962109 0.298087 0.106 Uiso 1 1 calc R U . . .
H23C H 0.645824 1.050615 0.225698 0.106 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
Br1 C1 1.889(2) . ?
O1 C7 1.215(3) . ?
O2 C10 1.188(3) . ?
O3 C20 1.368(2) . ?
O3 C17 1.381(2) . ?
O4 C22 1.213(3) . ?
C1 C6 1.384(3) . ?
C1 C2 1.386(3) . ?
C2 C3 1.374(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.400(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.398(3) . ?
C4 C7 1.483(3) . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.521(3) . ?
C8 C9 1.536(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C17 1.506(3) . ?
C9 C11 1.533(3) . ?
C9 C10 1.541(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.393(3) . ?
C11 C16 1.395(3) . ?
C12 C13 1.382(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.378(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.330(3) . ?
C18 C19 1.433(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.360(3) . ?
C19 C22 1.471(3) . ?
C20 C21 1.477(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.500(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C20 O3 C17 107.32(15) . . ?
C6 C1 C2 121.2(2) . . ?
C6 C1 Br1 120.03(17) . . ?
C2 C1 Br1 118.71(16) . . ?
C3 C2 C1 119.2(2) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 121.0(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.4(2) . . ?
C5 C4 C7 124.08(18) . . ?
C3 C4 C7 117.47(18) . . ?
C6 C5 C4 120.98(19) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 119.1(2) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
O1 C7 C4 120.23(19) . . ?
O1 C7 C8 118.1(2) . . ?
C4 C7 C8 121.65(17) . . ?
C7 C8 C9 111.36(16) . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C17 C9 C11 109.72(15) . . ?
C17 C9 C8 109.91(15) . . ?
C11 C9 C8 113.34(16) . . ?
C17 C9 C10 102.51(15) . . ?
C11 C9 C10 112.58(15) . . ?
C8 C9 C10 108.22(16) . . ?
O2 C10 C9 126.7(2) . . ?
O2 C10 H10 116.7 . . ?
C9 C10 H10 116.7 . . ?
C12 C11 C16 118.01(18) . . ?
C12 C11 C9 122.68(17) . . ?
C16 C11 C9 119.30(17) . . ?
C13 C12 C11 120.66(18) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 120.54(19) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 119.52(19) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C11 120.90(19) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C18 C17 O3 109.60(16) . . ?
C18 C17 C9 133.49(17) . . ?
O3 C17 C9 116.78(16) . . ?
C17 C18 C19 107.50(18) . . ?
C17 C18 H18 126.2 . . ?
C19 C18 H18 126.2 . . ?
C20 C19 C18 106.27(18) . . ?
C20 C19 C22 131.54(19) . . ?
C18 C19 C22 122.18(19) . . ?
C19 C20 O3 109.30(16) . . ?
C19 C20 C21 136.16(19) . . ?
O3 C20 C21 114.53(19) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 C22 C19 119.5(2) . . ?
O4 C22 C23 120.5(2) . . ?
C19 C22 C23 120.0(2) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -2.3(3) . . . . ?
Br1 C1 C2 C3 175.80(17) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C2 C3 C4 C7 -177.2(2) . . . . ?
C3 C4 C5 C6 -1.8(3) . . . . ?
C7 C4 C5 C6 175.8(2) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
C2 C1 C6 C5 1.2(3) . . . . ?
Br1 C1 C6 C5 -176.92(17) . . . . ?
C5 C4 C7 O1 -171.5(2) . . . . ?
C3 C4 C7 O1 6.2(3) . . . . ?
C5 C4 C7 C8 8.8(3) . . . . ?
C3 C4 C7 C8 -173.52(19) . . . . ?
O1 C7 C8 C9 31.4(3) . . . . ?
C4 C7 C8 C9 -148.93(18) . . . . ?
C7 C8 C9 C17 -168.36(16) . . . . ?
C7 C8 C9 C11 68.5(2) . . . . ?
C7 C8 C9 C10 -57.2(2) . . . . ?
C17 C9 C10 O2 -98.8(2) . . . . ?
C11 C9 C10 O2 19.0(3) . . . . ?
C8 C9 C10 O2 145.1(2) . . . . ?
C17 C9 C11 C12 -124.60(18) . . . . ?
C8 C9 C11 C12 -1.3(2) . . . . ?
C10 C9 C11 C12 121.93(19) . . . . ?
C17 C9 C11 C16 53.9(2) . . . . ?
C8 C9 C11 C16 177.16(16) . . . . ?
C10 C9 C11 C16 -59.6(2) . . . . ?
C16 C11 C12 C13 0.6(3) . . . . ?
C9 C11 C12 C13 179.11(18) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C14 C15 C16 C11 0.6(3) . . . . ?
C12 C11 C16 C15 -1.1(3) . . . . ?
C9 C11 C16 C15 -179.68(17) . . . . ?
C20 O3 C17 C18 0.5(2) . . . . ?
C20 O3 C17 C9 -175.94(16) . . . . ?
C11 C9 C17 C18 -98.2(3) . . . . ?
C8 C9 C17 C18 136.5(2) . . . . ?
C10 C9 C17 C18 21.6(3) . . . . ?
C11 C9 C17 O3 77.2(2) . . . . ?
C8 C9 C17 O3 -48.1(2) . . . . ?
C10 C9 C17 O3 -163.02(16) . . . . ?
O3 C17 C18 C19 -0.3(2) . . . . ?
C9 C17 C18 C19 175.3(2) . . . . ?
C17 C18 C19 C20 0.0(2) . . . . ?
C17 C18 C19 C22 179.5(2) . . . . ?
C18 C19 C20 O3 0.4(2) . . . . ?
C22 C19 C20 O3 -179.1(2) . . . . ?
C18 C19 C20 C21 179.3(3) . . . . ?
C22 C19 C20 C21 -0.2(4) . . . . ?
C17 O3 C20 C19 -0.5(2) . . . . ?
C17 O3 C20 C21 -179.70(19) . . . . ?
C20 C19 C22 O4 176.7(3) . . . . ?
C18 C19 C22 O4 -2.6(4) . . . . ?
C20 C19 C22 C23 -0.7(4) . . . . ?
C18 C19 C22 C23 179.9(2) . . . . ?

_refine_diff_density_max         0.382
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.048



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol and Acetone'
