# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_scp_a
_database_code_depnum_ccdc_archive 'CCDC 2331763'
loop_
_audit_author_name
_audit_author_address
'GAURAV JAISWAL'
;IIT Guwahati
India
;
_audit_update_record             
;
2024-02-08 deposited with the CCDC.	2024-04-15 downloaded from the CCDC.
;
_audit_creation_date             2023-09-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H15 Cl O2'
_chemical_formula_sum            'C25 H15 Cl O2'
_chemical_formula_weight         382.82
_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'
Cl Cl 0.1484 0.1585 '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                   16.591(10)
_cell_length_b                   7.190(4)
_cell_length_c                   15.695(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.373(17)
_cell_angle_gamma                90
_cell_volume                     1868.9(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9404
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.14
_cell_measurement_theta_min      2.81
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31619
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.322
_diffrn_reflns_theta_min         2.459
_diffrn_ambient_temperature      297.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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                3032
_reflns_number_total             3785
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3785
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.050
_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)+(0.0280P)²+0.9323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.1019
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C9(H9), C4(H4), C25(H25), C18(H18), C12(H12), C21(H21), C1(H1),
 C13(H13), C24(H24), C8(H8), C23(H23), C3(H3), C22(H22), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.48590(4) 0.90203(9) 0.63257(4) 0.0791(2) Uani 1 1 d . . . . .
O2 O 0.59956(9) 0.6469(2) 0.34654(8) 0.0695(4) Uani 1 1 d . . . . .
C11 C 0.66230(10) 0.4651(2) 0.55435(10) 0.0393(4) Uani 1 1 d . . . . .
C16 C 0.62016(9) 0.5725(2) 0.49303(10) 0.0401(4) Uani 1 1 d . . . . .
C10 C 0.72696(9) 0.3237(2) 0.53194(10) 0.0379(4) Uani 1 1 d . . . . .
C6 C 0.85301(10) 0.2939(2) 0.63312(10) 0.0432(4) Uani 1 1 d . . . . .
C5 C 0.80835(9) 0.3938(2) 0.57066(10) 0.0382(4) Uani 1 1 d . . . . .
O1 O 0.86242(11) 0.0243(3) 0.71896(12) 0.1004(6) Uani 1 1 d . . . . .
C19 C 0.73284(10) 0.2991(2) 0.43547(10) 0.0406(4) Uani 1 1 d . . . . .
C20 C 0.78421(10) 0.1444(2) 0.40566(10) 0.0425(4) Uani 1 1 d . . . . .
C15 C 0.56458(10) 0.7057(3) 0.51722(12) 0.0479(4) Uani 1 1 d . . . . .
H15 H 0.536234 0.777006 0.476102 0.058 Uiso 1 1 calc R U . . .
C17 C 0.63400(11) 0.5491(3) 0.40104(11) 0.0470(4) Uani 1 1 d . . . . .
C9 C 0.70384(11) 0.1370(2) 0.56777(11) 0.0472(4) Uani 1 1 d . . . . .
H9 H 0.655545 0.083971 0.546805 0.057 Uiso 1 1 calc R U . . .
C4 C 0.83860(11) 0.5623(3) 0.54271(12) 0.0507(4) Uani 1 1 d . . . . .
H4 H 0.809112 0.630751 0.501393 0.061 Uiso 1 1 calc R U . . .
C25 C 0.74677(11) 0.0005(3) 0.35948(12) 0.0535(5) Uani 1 1 d . . . . .
H25 H 0.691041 0.002566 0.348825 0.064 Uiso 1 1 calc R U . . .
C18 C 0.68996(11) 0.4030(3) 0.37883(11) 0.0480(4) Uani 1 1 d . . . . .
H18 H 0.696205 0.380750 0.321225 0.058 Uiso 1 1 calc R U . . .
C12 C 0.64682(11) 0.4920(3) 0.63989(11) 0.0522(5) Uani 1 1 d . . . . .
H12 H 0.673784 0.419271 0.681473 0.063 Uiso 1 1 calc R U . . .
C14 C 0.55219(10) 0.7302(3) 0.60186(12) 0.0488(4) Uani 1 1 d . . . . .
C21 C 0.86740(11) 0.1367(3) 0.42098(12) 0.0562(5) Uani 1 1 d . . . . .
H21 H 0.893891 0.230740 0.452166 0.067 Uiso 1 1 calc R U . . .
C1 C 0.92685(11) 0.3649(3) 0.66642(12) 0.0570(5) Uani 1 1 d . . . . .
H1 H 0.956270 0.299066 0.708739 0.068 Uiso 1 1 calc R U . . .
C13 C 0.59250(11) 0.6238(3) 0.66406(12) 0.0543(5) Uani 1 1 d . . . . .
H13 H 0.583086 0.640961 0.721362 0.065 Uiso 1 1 calc R U . . .
C24 C 0.79071(12) -0.1453(3) 0.32917(13) 0.0583(5) Uani 1 1 d . . . . .
H24 H 0.764538 -0.240668 0.298542 0.070 Uiso 1 1 calc R U . . .
C7 C 0.82393(12) 0.1127(3) 0.66414(12) 0.0570(5) Uani 1 1 d . . . . .
C8 C 0.74747(12) 0.0439(3) 0.62683(12) 0.0554(5) Uani 1 1 d . . . . .
H8 H 0.728393 -0.070031 0.645153 0.066 Uiso 1 1 calc R U . . .
C23 C 0.87308(12) -0.1502(3) 0.34408(13) 0.0581(5) Uani 1 1 d . . . . .
H23 H 0.902870 -0.247811 0.323080 0.070 Uiso 1 1 calc R U . . .
C3 C 0.91174(12) 0.6283(3) 0.57568(14) 0.0620(5) Uani 1 1 d . . . . .
H3 H 0.931459 0.740598 0.556136 0.074 Uiso 1 1 calc R U . . .
C22 C 0.91118(12) -0.0100(3) 0.39021(14) 0.0643(6) Uani 1 1 d . . . . .
H22 H 0.966897 -0.013606 0.400842 0.077 Uiso 1 1 calc R U . . .
C2 C 0.95632(12) 0.5290(3) 0.63777(13) 0.0631(5) Uani 1 1 d . . . . .
H2 H 1.005866 0.573938 0.659688 0.076 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 C14 1.7408(19) . ?
O2 C17 1.223(2) . ?
C11 C16 1.390(2) . ?
C11 C10 1.534(2) . ?
C11 C12 1.395(2) . ?
C16 C15 1.397(2) . ?
C16 C17 1.485(2) . ?
C10 C5 1.533(2) . ?
C10 C19 1.533(2) . ?
C10 C9 1.513(2) . ?
C6 C5 1.393(2) . ?
C6 C1 1.400(3) . ?
C6 C7 1.482(3) . ?
C5 C4 1.392(2) . ?
O1 C7 1.220(2) . ?
C19 C20 1.493(2) . ?
C19 C18 1.334(2) . ?
C20 C25 1.389(2) . ?
C20 C21 1.388(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.368(3) . ?
C17 C18 1.457(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.324(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.375(3) . ?
C25 H25 0.9300 . ?
C25 C24 1.377(3) . ?
C18 H18 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.376(3) . ?
C14 C13 1.382(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.383(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.364(3) . ?
C13 H13 0.9300 . ?
C24 H24 0.9300 . ?
C24 C23 1.373(3) . ?
C7 C8 1.452(3) . ?
C8 H8 0.9300 . ?
C23 H23 0.9300 . ?
C23 C22 1.373(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.386(3) . ?
C22 H22 0.9300 . ?
C2 H2 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
C16 C11 C10 122.65(15) . . ?
C16 C11 C12 118.41(16) . . ?
C12 C11 C10 118.91(14) . . ?
C11 C16 C15 120.38(16) . . ?
C11 C16 C17 120.65(15) . . ?
C15 C16 C17 118.97(15) . . ?
C5 C10 C11 107.65(13) . . ?
C5 C10 C19 108.89(13) . . ?
C19 C10 C11 112.91(13) . . ?
C9 C10 C11 107.85(14) . . ?
C9 C10 C5 112.38(14) . . ?
C9 C10 C19 107.25(13) . . ?
C5 C6 C1 119.50(17) . . ?
C5 C6 C7 120.97(16) . . ?
C1 C6 C7 119.52(16) . . ?
C6 C5 C10 121.96(15) . . ?
C4 C5 C10 119.11(14) . . ?
C4 C5 C6 118.93(16) . . ?
C20 C19 C10 117.80(14) . . ?
C18 C19 C10 122.04(15) . . ?
C18 C19 C20 120.03(15) . . ?
C25 C20 C19 118.20(16) . . ?
C21 C20 C19 123.75(15) . . ?
C21 C20 C25 118.05(16) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 C16 119.45(16) . . ?
C14 C15 H15 120.3 . . ?
O2 C17 C16 121.47(17) . . ?
O2 C17 C18 121.68(17) . . ?
C18 C17 C16 116.84(14) . . ?
C10 C9 H9 117.7 . . ?
C8 C9 C10 124.65(17) . . ?
C8 C9 H9 117.7 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.55(17) . . ?
C3 C4 H4 119.7 . . ?
C20 C25 H25 119.4 . . ?
C24 C25 C20 121.18(18) . . ?
C24 C25 H25 119.4 . . ?
C19 C18 C17 124.50(16) . . ?
C19 C18 H18 117.7 . . ?
C17 C18 H18 117.7 . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.41(17) . . ?
C13 C12 H12 119.3 . . ?
C15 C14 Cl1 119.60(14) . . ?
C15 C14 C13 121.38(17) . . ?
C13 C14 Cl1 119.00(15) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.48(18) . . ?
C22 C21 H21 119.8 . . ?
C6 C1 H1 119.5 . . ?
C2 C1 C6 121.02(18) . . ?
C2 C1 H1 119.5 . . ?
C12 C13 C14 118.96(17) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C25 C24 H24 119.9 . . ?
C23 C24 C25 120.14(18) . . ?
C23 C24 H24 119.9 . . ?
O1 C7 C6 121.52(19) . . ?
O1 C7 C8 121.06(19) . . ?
C8 C7 C6 117.41(16) . . ?
C9 C8 C7 122.61(18) . . ?
C9 C8 H8 118.7 . . ?
C7 C8 H8 118.7 . . ?
C24 C23 H23 120.2 . . ?
C22 C23 C24 119.59(18) . . ?
C22 C23 H23 120.2 . . ?
C4 C3 H3 119.7 . . ?
C4 C3 C2 120.62(19) . . ?
C2 C3 H3 119.7 . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.57(19) . . ?
C23 C22 H22 119.7 . . ?
C1 C2 C3 119.37(18) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?

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 C14 C13 C12 -177.96(15) . . . . ?
O2 C17 C18 C19 175.94(19) . . . . ?
C11 C16 C15 C14 0.3(3) . . . . ?
C11 C16 C17 O2 -177.38(17) . . . . ?
C11 C16 C17 C18 3.1(2) . . . . ?
C11 C10 C5 C6 117.24(17) . . . . ?
C11 C10 C5 C4 -62.70(19) . . . . ?
C11 C10 C19 C20 -170.61(14) . . . . ?
C11 C10 C19 C18 5.1(2) . . . . ?
C11 C10 C9 C8 -117.5(2) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C16 C11 C10 C5 113.80(17) . . . . ?
C16 C11 C10 C19 -6.4(2) . . . . ?
C16 C11 C10 C9 -124.72(16) . . . . ?
C16 C11 C12 C13 -1.3(3) . . . . ?
C16 C15 C14 Cl1 177.53(13) . . . . ?
C16 C15 C14 C13 -1.1(3) . . . . ?
C16 C17 C18 C19 -4.6(3) . . . . ?
C10 C11 C16 C15 -176.93(15) . . . . ?
C10 C11 C16 C17 2.5(2) . . . . ?
C10 C11 C12 C13 176.58(17) . . . . ?
C10 C5 C4 C3 -179.50(17) . . . . ?
C10 C19 C20 C25 114.94(18) . . . . ?
C10 C19 C20 C21 -65.5(2) . . . . ?
C10 C19 C18 C17 0.2(3) . . . . ?
C10 C9 C8 C7 -0.1(3) . . . . ?
C6 C5 C4 C3 0.6(3) . . . . ?
C6 C1 C2 C3 1.0(3) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C5 C10 C19 C20 69.89(18) . . . . ?
C5 C10 C19 C18 -114.38(18) . . . . ?
C5 C10 C9 C8 1.0(2) . . . . ?
C5 C6 C1 C2 -1.0(3) . . . . ?
C5 C6 C7 O1 -179.8(2) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C5 C4 C3 C2 -0.5(3) . . . . ?
O1 C7 C8 C9 179.4(2) . . . . ?
C19 C10 C5 C6 -120.04(16) . . . . ?
C19 C10 C5 C4 60.02(19) . . . . ?
C19 C10 C9 C8 120.64(19) . . . . ?
C19 C20 C25 C24 179.18(17) . . . . ?
C19 C20 C21 C22 -179.02(18) . . . . ?
C20 C19 C18 C17 175.82(16) . . . . ?
C20 C25 C24 C23 -0.2(3) . . . . ?
C20 C21 C22 C23 0.0(3) . . . . ?
C15 C16 C17 O2 2.0(3) . . . . ?
C15 C16 C17 C18 -177.44(16) . . . . ?
C15 C14 C13 C12 0.7(3) . . . . ?
C17 C16 C15 C14 -179.10(16) . . . . ?
C9 C10 C5 C6 -1.4(2) . . . . ?
C9 C10 C5 C4 178.69(15) . . . . ?
C9 C10 C19 C20 -51.95(19) . . . . ?
C9 C10 C19 C18 123.78(18) . . . . ?
C4 C3 C2 C1 -0.3(3) . . . . ?
C25 C20 C21 C22 0.5(3) . . . . ?
C25 C24 C23 C22 0.7(3) . . . . ?
C18 C19 C20 C25 -60.9(2) . . . . ?
C18 C19 C20 C21 118.7(2) . . . . ?
C12 C11 C16 C15 0.9(2) . . . . ?
C12 C11 C16 C17 -179.72(16) . . . . ?
C12 C11 C10 C5 -63.99(19) . . . . ?
C12 C11 C10 C19 175.79(15) . . . . ?
C12 C11 C10 C9 57.5(2) . . . . ?
C21 C20 C25 C24 -0.4(3) . . . . ?
C1 C6 C5 C10 -179.79(16) . . . . ?
C1 C6 C5 C4 0.2(2) . . . . ?
C1 C6 C7 O1 0.9(3) . . . . ?
C1 C6 C7 C8 -179.24(17) . . . . ?
C24 C23 C22 C21 -0.6(3) . . . . ?
C7 C6 C5 C10 0.9(2) . . . . ?
C7 C6 C5 C4 -179.17(16) . . . . ?
C7 C6 C1 C2 178.37(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
