# 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. 
# 
#######################################################################

data_xxx
_database_code_depnum_ccdc_archive 'CCDC 2327958'
loop_
_audit_author_name
_audit_author_address
'Dr. Ruchir Kant'
;CSIR CDRI, Lucknow
India
;
_audit_update_record             
;
2024-01-24 deposited with the CCDC.	2024-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 Cl O2'
_chemical_formula_weight         362.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.87220(10)
_cell_length_b                   11.3433(2)
_cell_length_c                   11.65270(10)
_cell_angle_alpha                102.5890(10)
_cell_angle_beta                 97.7710(10)
_cell_angle_gamma                108.9250(10)
_cell_volume                     936.44(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7596
_cell_measurement_theta_min      3.9850
_cell_measurement_theta_max      76.9960

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    1.907
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku'

_exptl_absorpt_correction_T_min  0.6791
_exptl_absorpt_correction_T_max  0.7630

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000

_diffrn_reflns_number            11487
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.99
_diffrn_reflns_theta_max         77.75
_reflns_number_total             3763
_reflns_number_gt                3369
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'



_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0529P)²+0.1743P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    Constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0070(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3763
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1105
_refine_ls_wR_factor_gt          0.1078
_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

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS


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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.59068(18) 0.28148(13) 0.06085(11) 0.0404(3) Uani 1 1 d . . .
C2 C 0.5103(2) 0.30371(14) -0.04284(13) 0.0479(3) Uani 1 1 d . . .
H2 H 0.5819 0.3659 -0.0747 0.057 Uiso 1 1 calc R . .
C3 C 0.3273(2) 0.23570(16) -0.09914(13) 0.0532(4) Uani 1 1 d . . .
H3 H 0.2763 0.2525 -0.1676 0.064 Uiso 1 1 calc R . .
C4 C 0.2210(2) 0.14281(17) -0.05328(14) 0.0575(4) Uani 1 1 d . . .
H4 H 0.0979 0.0958 -0.0913 0.069 Uiso 1 1 calc R . .
C5 C 0.2969(2) 0.11944(15) 0.04900(13) 0.0513(4) Uani 1 1 d . . .
H5 H 0.2239 0.0558 0.0787 0.062 Uiso 1 1 calc R . .
C6 C 0.48048(18) 0.18867(13) 0.10922(11) 0.0406(3) Uani 1 1 d . . .
C7 C 0.79052(18) 0.35592(13) 0.11521(11) 0.0409(3) Uani 1 1 d . . .
C8 C 0.86036(19) 0.49023(14) 0.13652(13) 0.0454(3) Uani 1 1 d . . .
H8 H 0.7832 0.5331 0.1163 0.054 Uiso 1 1 calc R . .
C9 C 1.0450(2) 0.55921(14) 0.18790(13) 0.0489(3) Uani 1 1 d . . .
C10 C 1.1643(2) 0.49934(17) 0.21739(14) 0.0550(4) Uani 1 1 d . . .
H10 H 1.2884 0.5474 0.2518 0.066 Uiso 1 1 calc R . .
C11 C 1.0950(2) 0.36566(18) 0.19444(17) 0.0602(4) Uani 1 1 d . . .
H11 H 1.1735 0.3232 0.2133 0.072 Uiso 1 1 calc R . .
C12 C 0.9106(2) 0.29454(15) 0.14384(14) 0.0515(4) Uani 1 1 d . . .
H12 H 0.8664 0.2048 0.1288 0.062 Uiso 1 1 calc R . .
C14 C 0.54675(18) 0.16171(13) 0.22336(12) 0.0408(3) Uani 1 1 d . . .
C15 C 0.5323(2) 0.03550(14) 0.22102(13) 0.0489(3) Uani 1 1 d . . .
H15 H 0.4854 -0.0292 0.1481 0.059 Uiso 1 1 calc R . .
C16 C 0.5860(2) 0.00418(15) 0.32449(15) 0.0544(4) Uani 1 1 d . . .
H16 H 0.5736 -0.0810 0.3211 0.065 Uiso 1 1 calc R . .
C17 C 0.6583(2) 0.09977(16) 0.43320(14) 0.0555(4) Uani 1 1 d . . .
H17 H 0.6969 0.0795 0.5029 0.067 Uiso 1 1 calc R . .
C18 C 0.6729(2) 0.22518(15) 0.43805(13) 0.0509(4) Uani 1 1 d . . .
H18 H 0.7215 0.2888 0.5116 0.061 Uiso 1 1 calc R . .
C19 C 0.61643(19) 0.25909(13) 0.33495(12) 0.0421(3) Uani 1 1 d . . .
C20 C 0.6227(2) 0.39105(13) 0.34304(12) 0.0435(3) Uani 1 1 d . . .
H20 H 0.5549 0.4021 0.2772 0.052 Uiso 1 1 calc R . .
C21 C 0.7144(2) 0.49628(14) 0.43379(13) 0.0531(4) Uani 1 1 d . . .
H21 H 0.7832 0.4899 0.5020 0.064 Uiso 1 1 calc R . .
C22 C 0.7088(2) 0.62297(14) 0.42827(12) 0.0469(3) Uani 1 1 d . . .
C23 C 0.8186(3) 0.84549(15) 0.53365(15) 0.0595(4) Uani 1 1 d . . .
H23A H 0.6964 0.8468 0.5098 0.071 Uiso 1 1 calc R . .
H23B H 0.8921 0.8782 0.4791 0.071 Uiso 1 1 calc R . .
C24 C 0.9056(3) 0.92705(16) 0.66004(16) 0.0640(4) Uani 1 1 d . . .
H24A H 0.9186 1.0153 0.6655 0.096 Uiso 1 1 calc R . .
H24B H 1.0248 0.9230 0.6833 0.096 Uiso 1 1 calc R . .
H24C H 0.8295 0.8955 0.7128 0.096 Uiso 1 1 calc R . .
Cl1 Cl 1.12926(6) 0.72767(4) 0.21763(5) 0.07425(18) Uani 1 1 d . . .
O1 O 0.80764(17) 0.71540(10) 0.52957(9) 0.0587(3) Uani 1 1 d . . .
O2 O 0.62772(18) 0.64406(11) 0.34428(10) 0.0644(3) 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 1.3978(19) . ?
C1 C6 1.4061(19) . ?
C1 C7 1.4916(18) . ?
C2 C3 1.379(2) . ?
C3 C4 1.375(2) . ?
C4 C5 1.377(2) . ?
C5 C6 1.3954(19) . ?
C6 C14 1.4926(19) . ?
C7 C12 1.390(2) . ?
C7 C8 1.3927(19) . ?
C8 C9 1.380(2) . ?
C9 C10 1.375(2) . ?
C9 Cl1 1.7432(15) . ?
C10 C11 1.384(2) . ?
C11 C12 1.381(2) . ?
C14 C15 1.3928(19) . ?
C14 C19 1.4142(18) . ?
C15 C16 1.380(2) . ?
C16 C17 1.382(2) . ?
C17 C18 1.377(2) . ?
C18 C19 1.399(2) . ?
C19 C20 1.4632(19) . ?
C20 C21 1.322(2) . ?
C21 C22 1.467(2) . ?
C22 O2 1.2061(17) . ?
C22 O1 1.3346(17) . ?
C23 O1 1.4398(18) . ?
C23 C24 1.489(2) . ?

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 118.72(12) . . ?
C2 C1 C7 118.81(12) . . ?
C6 C1 C7 122.47(12) . . ?
C3 C2 C1 121.60(14) . . ?
C4 C3 C2 119.56(14) . . ?
C3 C4 C5 119.91(14) . . ?
C4 C5 C6 121.75(14) . . ?
C5 C6 C1 118.42(13) . . ?
C5 C6 C14 117.67(12) . . ?
C1 C6 C14 123.89(12) . . ?
C12 C7 C8 118.73(13) . . ?
C12 C7 C1 121.71(13) . . ?
C8 C7 C1 119.56(12) . . ?
C9 C8 C7 119.53(13) . . ?
C10 C9 C8 122.08(14) . . ?
C10 C9 Cl1 118.89(12) . . ?
C8 C9 Cl1 119.03(12) . . ?
C9 C10 C11 118.23(14) . . ?
C12 C11 C10 120.80(15) . . ?
C11 C12 C7 120.61(14) . . ?
C15 C14 C19 118.82(12) . . ?
C15 C14 C6 119.03(12) . . ?
C19 C14 C6 122.09(12) . . ?
C16 C15 C14 121.53(13) . . ?
C15 C16 C17 119.78(14) . . ?
C18 C17 C16 119.81(14) . . ?
C17 C18 C19 121.57(14) . . ?
C18 C19 C14 118.46(13) . . ?
C18 C19 C20 120.80(12) . . ?
C14 C19 C20 120.70(12) . . ?
C21 C20 C19 127.10(13) . . ?
C20 C21 C22 120.85(14) . . ?
O2 C22 O1 123.03(14) . . ?
O2 C22 C21 125.77(13) . . ?
O1 C22 C21 111.20(12) . . ?
O1 C23 C24 107.25(13) . . ?
C22 O1 C23 116.57(12) . . ?

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 -0.9(2) . . . . ?
C7 C1 C2 C3 178.35(13) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C4 C5 C6 C1 -2.1(2) . . . . ?
C4 C5 C6 C14 176.41(14) . . . . ?
C2 C1 C6 C5 2.23(19) . . . . ?
C7 C1 C6 C5 -177.04(12) . . . . ?
C2 C1 C6 C14 -176.18(12) . . . . ?
C7 C1 C6 C14 4.5(2) . . . . ?
C2 C1 C7 C12 -129.63(14) . . . . ?
C6 C1 C7 C12 49.65(19) . . . . ?
C2 C1 C7 C8 49.42(18) . . . . ?
C6 C1 C7 C8 -131.31(14) . . . . ?
C12 C7 C8 C9 -1.6(2) . . . . ?
C1 C7 C8 C9 179.37(12) . . . . ?
C7 C8 C9 C10 1.1(2) . . . . ?
C7 C8 C9 Cl1 -178.37(10) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
Cl1 C9 C10 C11 179.31(12) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C10 C11 C12 C7 -0.2(3) . . . . ?
C8 C7 C12 C11 1.1(2) . . . . ?
C1 C7 C12 C11 -179.80(14) . . . . ?
C5 C6 C14 C15 57.63(18) . . . . ?
C1 C6 C14 C15 -123.95(15) . . . . ?
C5 C6 C14 C19 -119.57(15) . . . . ?
C1 C6 C14 C19 58.85(19) . . . . ?
C19 C14 C15 C16 -0.7(2) . . . . ?
C6 C14 C15 C16 -177.95(13) . . . . ?
C14 C15 C16 C17 -0.9(2) . . . . ?
C15 C16 C17 C18 1.3(2) . . . . ?
C16 C17 C18 C19 -0.1(2) . . . . ?
C17 C18 C19 C14 -1.4(2) . . . . ?
C17 C18 C19 C20 176.32(15) . . . . ?
C15 C14 C19 C18 1.8(2) . . . . ?
C6 C14 C19 C18 178.97(13) . . . . ?
C15 C14 C19 C20 -175.97(13) . . . . ?
C6 C14 C19 C20 1.2(2) . . . . ?
C18 C19 C20 C21 16.3(2) . . . . ?
C14 C19 C20 C21 -166.03(15) . . . . ?
C19 C20 C21 C22 179.39(14) . . . . ?
C20 C21 C22 O2 -1.5(3) . . . . ?
C20 C21 C22 O1 178.93(15) . . . . ?
O2 C22 O1 C23 -1.8(2) . . . . ?
C21 C22 O1 C23 177.83(14) . . . . ?
C24 C23 O1 C22 170.27(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.941
_diffrn_reflns_theta_full        77.75
_diffrn_measured_fraction_theta_full 0.941
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.035



####################################################################
#                         END of data
####################################################################

