# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_KB418_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2254463'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2023-04-06 deposited with the CCDC.	2023-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 Cl O2'
_chemical_formula_sum            'C19 H15 Cl O2'
_chemical_formula_weight         310.76

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   16.4838(4)
_cell_length_b                   11.3226(3)
_cell_length_c                   8.5334(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.0460(10)
_cell_angle_gamma                90
_cell_volume                     1576.99(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5539
_cell_measurement_theta_min      2.496
_cell_measurement_theta_max      23.0735

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.246
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6286
_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
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21052
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.189
_diffrn_reflns_theta_max         28.269
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3888
_reflns_number_gt                2240
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0625P)²+0.3371P] 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         3888
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1462
_refine_ls_wR_factor_gt          0.1168
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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 0.75160(11) 0.28888(18) 0.8350(2) 0.0591(5) Uani 1 1 d . . . . .
H1 H 0.757197 0.215200 0.789510 0.071 Uiso 1 1 calc R U . . .
C2 C 0.81639(11) 0.3412(2) 0.9312(2) 0.0650(5) Uani 1 1 d . . . . .
C3 C 0.80917(13) 0.4496(2) 1.0006(2) 0.0687(6) Uani 1 1 d . . . . .
H3 H 0.853626 0.481711 1.065826 0.082 Uiso 1 1 calc R U . . .
C4 C 0.73608(12) 0.51105(19) 0.9737(2) 0.0612(5) Uani 1 1 d . . . . .
H4 H 0.730978 0.584632 1.019780 0.073 Uiso 1 1 calc R U . . .
C5 C 0.67069(10) 0.46115(16) 0.8771(2) 0.0508(4) Uani 1 1 d . . . . .
C6 C 0.67840(10) 0.35000(16) 0.8088(2) 0.0471(4) Uani 1 1 d . . . . .
C7 C 0.59898(10) 0.32153(17) 0.7124(2) 0.0519(4) Uani 1 1 d . . . . .
C8 C 0.54518(10) 0.42256(18) 0.7318(2) 0.0548(5) Uani 1 1 d . . . . .
C9 C 0.58746(11) 0.50325(18) 0.8261(2) 0.0577(5) Uani 1 1 d . . . . .
H9 H 0.566701 0.575293 0.854572 0.069 Uiso 1 1 calc R U . . .
C10 C 0.58211(14) 0.2273(2) 0.6230(3) 0.0743(6) Uani 1 1 d . . . . .
H00B H 0.530885 0.219471 0.562572 0.089 Uiso 1 1 calc R U . . .
H00C H 0.621427 0.168732 0.620364 0.089 Uiso 1 1 calc R U . . .
C11 C 0.45893(11) 0.4339(2) 0.6504(2) 0.0658(6) Uani 1 1 d . . . . .
H00I H 0.457742 0.409675 0.541071 0.079 Uiso 1 1 calc R U . . .
H00K H 0.443757 0.516657 0.649892 0.079 Uiso 1 1 calc R U . . .
C12 C 0.39450(10) 0.36405(17) 0.7205(2) 0.0519(4) Uani 1 1 d . . . . .
C13 C 0.30857(10) 0.37458(15) 0.6422(2) 0.0476(4) Uani 1 1 d . . . . .
C14 C 0.24890(11) 0.29996(17) 0.6882(2) 0.0591(5) Uani 1 1 d . . . . .
H14 H 0.263421 0.244596 0.767728 0.071 Uiso 1 1 calc R U . . .
C15 C 0.16902(12) 0.30728(19) 0.6176(3) 0.0682(6) Uani 1 1 d . . . . .
H15 H 0.129820 0.257205 0.649927 0.082 Uiso 1 1 calc R U . . .
C16 C 0.14645(11) 0.38849(18) 0.4989(2) 0.0577(5) Uani 1 1 d . . . . .
C17 C 0.20378(11) 0.46438(18) 0.4524(2) 0.0598(5) Uani 1 1 d . . . . .
H17 H 0.188621 0.520557 0.374280 0.072 Uiso 1 1 calc R U . . .
C18 C 0.28415(11) 0.45590(17) 0.5235(2) 0.0578(5) Uani 1 1 d . . . . .
H18 H 0.323060 0.506275 0.490760 0.069 Uiso 1 1 calc R U . . .
C19 C 0.03931(13) 0.4668(2) 0.3085(3) 0.0858(7) Uani 1 1 d . . . . .
H00L H 0.067933 0.450354 0.220411 0.129 Uiso 1 1 calc R U . . .
H19 H 0.050476 0.546387 0.343746 0.129 Uiso 1 1 calc R U . . .
H00N H -0.018514 0.457264 0.276577 0.129 Uiso 1 1 calc R U . . .
Cl1 Cl 0.91024(4) 0.26788(7) 0.96222(10) 0.1044(3) Uani 1 1 d . . . . .
O1 O 0.41234(8) 0.30127(14) 0.83583(17) 0.0740(4) Uani 1 1 d . . . . .
O2 O 0.06600(8) 0.38726(15) 0.4340(2) 0.0821(5) 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 1.382(2) . ?
C1 C2 1.386(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(3) . ?
C2 Cl1 1.743(2) . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.400(3) . ?
C5 C9 1.460(2) . ?
C6 C7 1.481(2) . ?
C7 C10 1.318(3) . ?
C7 C8 1.471(3) . ?
C8 C9 1.345(3) . ?
C8 C11 1.498(2) . ?
C9 H9 0.9300 . ?
C10 H00B 0.9300 . ?
C10 H00C 0.9300 . ?
C11 C12 1.513(3) . ?
C11 H00I 0.9700 . ?
C11 H00K 0.9700 . ?
C12 O1 1.216(2) . ?
C12 C13 1.484(2) . ?
C13 C18 1.386(2) . ?
C13 C14 1.394(2) . ?
C14 C15 1.372(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(3) . ?
C15 H15 0.9300 . ?
C16 O2 1.364(2) . ?
C16 C17 1.376(3) . ?
C17 C18 1.381(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 O2 1.421(3) . ?
C19 H00L 0.9600 . ?
C19 H19 0.9600 . ?
C19 H00N 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 117.71(19) . . ?
C6 C1 H1 121.1 . . ?
C2 C1 H1 121.1 . . ?
C3 C2 C1 122.04(19) . . ?
C3 C2 Cl1 119.23(16) . . ?
C1 C2 Cl1 118.73(18) . . ?
C2 C3 C4 120.26(18) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 118.80(19) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 120.46(17) . . ?
C4 C5 C9 131.75(18) . . ?
C6 C5 C9 107.79(15) . . ?
C1 C6 C5 120.72(16) . . ?
C1 C6 C7 131.67(17) . . ?
C5 C6 C7 107.59(15) . . ?
C10 C7 C8 127.79(18) . . ?
C10 C7 C6 126.59(19) . . ?
C8 C7 C6 105.55(15) . . ?
C9 C8 C7 108.99(15) . . ?
C9 C8 C11 126.71(19) . . ?
C7 C8 C11 124.21(18) . . ?
C8 C9 C5 110.06(17) . . ?
C8 C9 H9 125.0 . . ?
C5 C9 H9 125.0 . . ?
C7 C10 H00B 120.0 . . ?
C7 C10 H00C 120.0 . . ?
H00B C10 H00C 120.0 . . ?
C8 C11 C12 116.44(16) . . ?
C8 C11 H00I 108.2 . . ?
C12 C11 H00I 108.2 . . ?
C8 C11 H00K 108.2 . . ?
C12 C11 H00K 108.2 . . ?
H00I C11 H00K 107.3 . . ?
O1 C12 C13 121.25(16) . . ?
O1 C12 C11 121.45(16) . . ?
C13 C12 C11 117.31(15) . . ?
C18 C13 C14 117.66(16) . . ?
C18 C13 C12 122.93(16) . . ?
C14 C13 C12 119.41(16) . . ?
C15 C14 C13 120.75(18) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 120.42(18) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
O2 C16 C17 123.88(18) . . ?
O2 C16 C15 115.98(17) . . ?
C17 C16 C15 120.14(17) . . ?
C16 C17 C18 119.03(18) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C17 C18 C13 121.98(17) . . ?
C17 C18 H18 119.0 . . ?
C13 C18 H18 119.0 . . ?
O2 C19 H00L 109.5 . . ?
O2 C19 H19 109.5 . . ?
H00L C19 H19 109.5 . . ?
O2 C19 H00N 109.5 . . ?
H00L C19 H00N 109.5 . . ?
H19 C19 H00N 109.5 . . ?
C16 O2 C19 118.71(17) . . ?

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 0.5(3) . . . . ?
C6 C1 C2 Cl1 -178.36(14) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
Cl1 C2 C3 C4 177.98(16) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C3 C4 C5 C9 -179.58(19) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C2 C1 C6 C7 178.93(18) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C9 C5 C6 C1 179.20(16) . . . . ?
C4 C5 C6 C7 -179.73(16) . . . . ?
C9 C5 C6 C7 0.29(19) . . . . ?
C1 C6 C7 C10 -2.2(3) . . . . ?
C5 C6 C7 C10 176.55(19) . . . . ?
C1 C6 C7 C8 -179.54(19) . . . . ?
C5 C6 C7 C8 -0.79(19) . . . . ?
C10 C7 C8 C9 -176.3(2) . . . . ?
C6 C7 C8 C9 1.0(2) . . . . ?
C10 C7 C8 C11 0.6(3) . . . . ?
C6 C7 C8 C11 177.85(16) . . . . ?
C7 C8 C9 C5 -0.9(2) . . . . ?
C11 C8 C9 C5 -177.60(17) . . . . ?
C4 C5 C9 C8 -179.6(2) . . . . ?
C6 C5 C9 C8 0.4(2) . . . . ?
C9 C8 C11 C12 -105.0(2) . . . . ?
C7 C8 C11 C12 78.8(2) . . . . ?
C8 C11 C12 O1 -0.8(3) . . . . ?
C8 C11 C12 C13 179.64(17) . . . . ?
O1 C12 C13 C18 171.68(19) . . . . ?
C11 C12 C13 C18 -8.7(3) . . . . ?
O1 C12 C13 C14 -8.5(3) . . . . ?
C11 C12 C13 C14 171.15(18) . . . . ?
C18 C13 C14 C15 0.1(3) . . . . ?
C12 C13 C14 C15 -179.74(18) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 O2 178.73(19) . . . . ?
C14 C15 C16 C17 -1.2(3) . . . . ?
O2 C16 C17 C18 -178.35(18) . . . . ?
C15 C16 C17 C18 1.6(3) . . . . ?
C16 C17 C18 C13 -1.1(3) . . . . ?
C14 C13 C18 C17 0.3(3) . . . . ?
C12 C13 C18 C17 -179.87(18) . . . . ?
C17 C16 O2 C19 1.5(3) . . . . ?
C15 C16 O2 C19 -178.5(2) . . . . ?

_refine_diff_density_max         0.156
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.034

