# Supplementary Information (SI) for ChemComm.
# 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. 
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#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2149906'
loop_
_audit_author_name
_audit_author_address
'Soumitra Maity'
;Indian Institute of Technology (ISM) Dhanbad
India
;
_audit_update_record             
;
2022-02-03 deposited with the CCDC.	2025-04-09 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         ?
_chemical_formula_sum            'C17 H15 Br O'
_chemical_formula_weight         315.20

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.556(4)
_cell_length_b                   5.9633(7)
_cell_length_c                   21.912(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.089(15)
_cell_angle_gamma                90
_cell_volume                     2925.9(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1600
_cell_measurement_theta_min      3.5310
_cell_measurement_theta_max      24.1480

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    2.799
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.42583
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6972
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.955
_diffrn_reflns_theta_max         26.991
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3150
_reflns_number_gt                1640
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0426P)²+0.0993P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00053(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3150
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1041
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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 0.64754(12) 0.5327(4) 0.50189(10) 0.0517(6) Uani 1 1 d . . . . .
C2 C 0.65427(12) 0.3287(4) 0.47404(11) 0.0566(7) Uani 1 1 d . . . . .
H2 H 0.692160 0.266744 0.482515 0.068 Uiso 1 1 calc R U . . .
C3 C 0.60549(14) 0.2171(4) 0.43400(11) 0.0633(7) Uani 1 1 d . . . . .
H3 H 0.610542 0.080411 0.415923 0.076 Uiso 1 1 calc R U . . .
C4 C 0.54929(13) 0.3091(4) 0.42094(13) 0.0681(7) Uani 1 1 d . . . . .
C5 C 0.54169(13) 0.5119(5) 0.44627(13) 0.0789(8) Uani 1 1 d . . . . .
H5 H 0.503854 0.575457 0.436270 0.095 Uiso 1 1 calc R U . . .
C6 C 0.59033(14) 0.6220(4) 0.48671(13) 0.0678(8) Uani 1 1 d . . . . .
H6 H 0.584756 0.759174 0.504232 0.081 Uiso 1 1 calc R U . . .
C7 C 0.70178(13) 0.6388(4) 0.54728(11) 0.0571(7) Uani 1 1 d . . . . .
C10 C 0.68406(11) 0.9855(4) 0.68718(10) 0.0541(6) Uani 1 1 d . . . . .
C11 C 0.67743(12) 0.8946(4) 0.74264(12) 0.0624(7) Uani 1 1 d . . . . .
H11 H 0.694748 0.756615 0.757228 0.075 Uiso 1 1 calc R U . . .
C12 C 0.64575(14) 1.0046(5) 0.77647(12) 0.0754(8) Uani 1 1 d . . . . .
H12 H 0.642028 0.938569 0.813498 0.090 Uiso 1 1 calc R U . . .
C13 C 0.61918(13) 1.2103(6) 0.75733(14) 0.0753(8) Uani 1 1 d . . . . .
C14 C 0.62563(14) 1.3005(5) 0.70171(15) 0.0788(8) Uani 1 1 d . . . . .
H14 H 0.608241 1.438441 0.687141 0.095 Uiso 1 1 calc R U . . .
C15 C 0.65728(13) 1.1905(4) 0.66745(13) 0.0705(8) Uani 1 1 d . . . . .
H15 H 0.660696 1.255645 0.630191 0.085 Uiso 1 1 calc R U . . .
C16 C 0.71859(12) 0.8635(4) 0.65157(10) 0.0547(7) Uani 1 1 d . . . . .
H16 H 0.737215 0.724434 0.672107 0.066 Uiso 1 1 calc R U . . .
C17 C 0.69616(12) 0.8554(4) 0.57764(11) 0.0585(7) Uani 1 1 d . . . . .
H17 H 0.660978 0.946409 0.556209 0.070 Uiso 1 1 calc R U . . .
C18 C 0.75178(13) 0.9793(5) 0.61304(12) 0.0707(8) Uani 1 1 d . . . . .
H18A H 0.789615 0.915182 0.613028 0.085 Uiso 1 1 calc R U . . .
H18B H 0.750371 1.141861 0.611701 0.085 Uiso 1 1 calc R U . . .
C19 C 0.58446(16) 1.3322(6) 0.79490(16) 0.1167(13) Uani 1 1 d . . . . .
H19A H 0.608709 1.345732 0.838936 0.175 Uiso 1 1 calc R U . . .
H19B H 0.548917 1.249292 0.792590 0.175 Uiso 1 1 calc R U . . .
H19C H 0.573729 1.478923 0.776992 0.175 Uiso 1 1 calc R U . . .
Br9 Br 0.48284(2) 0.15121(6) 0.36756(2) 0.1223(3) Uani 1 1 d . . . . .
O8 O 0.75020(9) 0.5440(3) 0.56037(8) 0.0777(6) 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 C6 1.390(4) . ?
C1 C2 1.392(3) . ?
C1 C7 1.494(4) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(4) . ?
C4 Br9 1.889(3) . ?
C5 C6 1.378(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O8 1.225(3) . ?
C7 C17 1.477(3) . ?
C10 C11 1.383(3) . ?
C10 C15 1.382(3) . ?
C10 C16 1.481(3) . ?
C11 C12 1.371(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.383(4) . ?
C13 C19 1.514(4) . ?
C14 C15 1.377(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C18 1.487(3) . ?
C16 C17 1.541(3) . ?
C16 H16 0.9800 . ?
C17 C18 1.495(4) . ?
C17 H17 0.9800 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C6 C1 C2 117.7(2) . . ?
C6 C1 C7 124.2(2) . . ?
C2 C1 C7 118.1(2) . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 Br9 120.3(2) . . ?
C3 C4 Br9 119.2(2) . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 121.5(2) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
O8 C7 C17 120.3(3) . . ?
O8 C7 C1 120.1(2) . . ?
C17 C7 C1 119.5(2) . . ?
C11 C10 C15 117.2(2) . . ?
C11 C10 C16 120.0(2) . . ?
C15 C10 C16 122.8(2) . . ?
C12 C11 C10 121.1(2) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 122.1(3) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C14 C13 C12 116.7(3) . . ?
C14 C13 C19 121.2(3) . . ?
C12 C13 C19 122.1(3) . . ?
C15 C14 C13 121.4(3) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C10 121.5(2) . . ?
C14 C15 H15 119.2 . . ?
C10 C15 H15 119.2 . . ?
C10 C16 C18 122.9(2) . . ?
C10 C16 C17 120.3(2) . . ?
C18 C16 C17 59.13(15) . . ?
C10 C16 H16 114.5 . . ?
C18 C16 H16 114.5 . . ?
C17 C16 H16 114.5 . . ?
C7 C17 C18 118.6(3) . . ?
C7 C17 C16 116.9(2) . . ?
C18 C17 C16 58.63(16) . . ?
C7 C17 H17 116.7 . . ?
C18 C17 H17 116.7 . . ?
C16 C17 H17 116.7 . . ?
C16 C18 C17 62.24(17) . . ?
C16 C18 H18A 117.5 . . ?
C17 C18 H18A 117.5 . . ?
C16 C18 H18B 117.5 . . ?
C17 C18 H18B 117.5 . . ?
H18A C18 H18B 114.6 . . ?
C13 C19 H19A 109.5 . . ?
C13 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C13 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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 -1.5(3) . . . . ?
C7 C1 C2 C3 177.0(2) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
C2 C3 C4 Br9 -178.66(18) . . . . ?
C3 C4 C5 C6 -2.0(4) . . . . ?
Br9 C4 C5 C6 178.0(2) . . . . ?
C4 C5 C6 C1 0.8(4) . . . . ?
C2 C1 C6 C5 0.9(4) . . . . ?
C7 C1 C6 C5 -177.6(2) . . . . ?
C6 C1 C7 O8 176.6(2) . . . . ?
C2 C1 C7 O8 -1.8(3) . . . . ?
C6 C1 C7 C17 -1.6(4) . . . . ?
C2 C1 C7 C17 179.98(19) . . . . ?
C15 C10 C11 C12 -0.2(4) . . . . ?
C16 C10 C11 C12 179.9(2) . . . . ?
C10 C11 C12 C13 -0.2(4) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
C11 C12 C13 C19 -179.7(3) . . . . ?
C12 C13 C14 C15 -0.3(4) . . . . ?
C19 C13 C14 C15 179.9(3) . . . . ?
C13 C14 C15 C10 -0.1(4) . . . . ?
C11 C10 C15 C14 0.4(4) . . . . ?
C16 C10 C15 C14 -179.7(2) . . . . ?
C11 C10 C16 C18 -150.4(2) . . . . ?
C15 C10 C16 C18 29.8(4) . . . . ?
C11 C10 C16 C17 138.9(2) . . . . ?
C15 C10 C16 C17 -41.0(3) . . . . ?
O8 C7 C17 C18 12.9(3) . . . . ?
C1 C7 C17 C18 -168.9(2) . . . . ?
O8 C7 C17 C16 -54.2(3) . . . . ?
C1 C7 C17 C16 124.0(2) . . . . ?
C10 C16 C17 C7 -138.8(2) . . . . ?
C18 C16 C17 C7 108.7(3) . . . . ?
C10 C16 C17 C18 112.5(3) . . . . ?
C10 C16 C18 C17 -108.2(3) . . . . ?
C7 C17 C18 C16 -105.6(2) . . . . ?

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.040



