# 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_b_a
_database_code_depnum_ccdc_archive 'CCDC 2286699'
loop_
_audit_author_name
_audit_author_address
'Simra Faraz'
;IIT Guwahati
India
;
_audit_update_record             
;
2023-08-04 deposited with the CCDC.	2023-11-20 downloaded from the CCDC.
;
_audit_creation_date             2023-07-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H9 Cl O3'
_chemical_formula_sum            'C17 H9 Cl O3'
_chemical_formula_weight         296.69
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   25.055(6)
_cell_length_b                   3.8926(9)
_cell_length_c                   13.226(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1290.0(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7452
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.21
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5638
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1511 before and 0.0816 after correction.
The Ratio of minimum to maximum transmission is 0.7563.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27222
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.991
_diffrn_reflns_theta_min         2.239
_diffrn_ambient_temperature      297.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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         0.913
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1868
_reflns_number_total             2527
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 683 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2527
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.142
_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)+(0.0220P)²+0.3017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0744
_refine_ls_wR_factor_ref         0.0832
_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:
 C10(H10), C16(H16), C17(H17), C3(H3), C13(H13), C14(H14), C5(H5), C4(H4),
 C6(H6)
;
_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 0.25775(5) 0.4073(4) 0.08107(10) 0.0700(4) Uani 1 1 d . . . . .
O1 O 0.36807(10) 0.5224(8) 0.5396(2) 0.0404(7) Uani 1 1 d . . . . .
O2 O 0.48473(12) 0.7854(9) 0.7375(2) 0.0546(9) Uani 1 1 d . . . . .
O3 O 0.52894(14) 1.0370(10) 0.6122(3) 0.0719(11) Uani 1 1 d . . . . .
C1 C 0.40441(16) 0.5987(11) 0.6122(3) 0.0391(11) Uani 1 1 d . . . . .
C11 C 0.38858(17) 0.6504(11) 0.4497(3) 0.0377(11) Uani 1 1 d . . . . .
C12 C 0.35648(16) 0.5937(10) 0.3597(4) 0.0371(10) Uani 1 1 d . . . . .
C10 C 0.43625(17) 0.8047(12) 0.4669(3) 0.0428(12) Uani 1 1 d . . . . .
H10 H 0.457956 0.912124 0.419377 0.051 Uiso 1 1 calc R U . . .
C16 C 0.27676(18) 0.3815(11) 0.2808(3) 0.0448(12) Uani 1 1 d . . . . .
H16 H 0.243593 0.275401 0.285410 0.054 Uiso 1 1 calc R U . . .
C9 C 0.44642(16) 0.7690(11) 0.5727(4) 0.0419(11) Uani 1 1 d . . . . .
C8 C 0.48996(19) 0.8769(14) 0.6365(4) 0.0523(14) Uani 1 1 d . . . . .
C15 C 0.29578(18) 0.4836(12) 0.1895(3) 0.0452(12) Uani 1 1 d . . . . .
C17 C 0.30681(16) 0.4357(11) 0.3664(3) 0.0413(11) Uani 1 1 d . . . . .
H17 H 0.293837 0.366348 0.429062 0.050 Uiso 1 1 calc R U . . .
C7 C 0.44138(18) 0.6121(12) 0.7766(4) 0.0454(12) Uani 1 1 d . . . . .
C3 C 0.35518(18) 0.3381(12) 0.7597(3) 0.0490(13) Uani 1 1 d . . . . .
H3 H 0.326334 0.269302 0.720342 0.059 Uiso 1 1 calc R U . . .
C13 C 0.37455(18) 0.6970(13) 0.2661(4) 0.0465(12) Uani 1 1 d . . . . .
H13 H 0.407639 0.803670 0.260782 0.056 Uiso 1 1 calc R U . . .
C2 C 0.39847(17) 0.5086(12) 0.7158(3) 0.0416(12) Uani 1 1 d . . . . .
C14 C 0.34451(18) 0.6451(12) 0.1805(3) 0.0480(12) Uani 1 1 d . . . . .
H14 H 0.356832 0.717472 0.117689 0.058 Uiso 1 1 calc R U . . .
C5 C 0.3992(2) 0.3754(14) 0.9199(4) 0.0585(14) Uani 1 1 d . . . . .
H5 H 0.399630 0.326630 0.988729 0.070 Uiso 1 1 calc R U . . .
C4 C 0.3559(2) 0.2730(13) 0.8629(4) 0.0567(13) Uani 1 1 d . . . . .
H4 H 0.327374 0.160965 0.893399 0.068 Uiso 1 1 calc R U . . .
C6 C 0.4412(2) 0.5450(13) 0.8787(4) 0.0554(14) Uani 1 1 d . . . . .
H6 H 0.469612 0.615174 0.919052 0.067 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 C15 1.747(4) . ?
O1 C1 1.356(5) . ?
O1 C11 1.389(5) . ?
O2 C8 1.389(5) . ?
O2 C7 1.379(5) . ?
O3 C8 1.202(5) . ?
C1 C9 1.349(6) . ?
C1 C2 1.422(6) . ?
C11 C12 1.453(6) . ?
C11 C10 1.356(6) . ?
C12 C17 1.391(5) . ?
C12 C13 1.378(6) . ?
C10 H10 0.9300 . ?
C10 C9 1.430(6) . ?
C16 H16 0.9300 . ?
C16 C15 1.357(6) . ?
C16 C17 1.377(6) . ?
C9 C8 1.441(6) . ?
C15 C14 1.378(6) . ?
C17 H17 0.9300 . ?
C7 C2 1.402(6) . ?
C7 C6 1.375(7) . ?
C3 H3 0.9300 . ?
C3 C2 1.398(6) . ?
C3 C4 1.388(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(6) . ?
C14 H14 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.381(7) . ?
C5 C6 1.356(7) . ?
C4 H4 0.9300 . ?
C6 H6 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
C1 O1 C11 106.2(3) . . ?
C7 O2 C8 124.1(4) . . ?
O1 C1 C2 123.9(4) . . ?
C9 C1 O1 110.9(4) . . ?
C9 C1 C2 125.2(4) . . ?
O1 C11 C12 116.3(4) . . ?
C10 C11 O1 109.9(4) . . ?
C10 C11 C12 133.8(4) . . ?
C17 C12 C11 120.7(4) . . ?
C13 C12 C11 120.6(4) . . ?
C13 C12 C17 118.7(4) . . ?
C11 C10 H10 126.9 . . ?
C11 C10 C9 106.1(4) . . ?
C9 C10 H10 126.9 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.7(4) . . ?
C17 C16 H16 120.2 . . ?
C1 C9 C10 106.7(4) . . ?
C1 C9 C8 120.5(5) . . ?
C10 C9 C8 132.8(5) . . ?
O2 C8 C9 114.6(5) . . ?
O3 C8 O2 117.8(4) . . ?
O3 C8 C9 127.5(5) . . ?
C16 C15 Cl1 119.3(4) . . ?
C16 C15 C14 121.4(4) . . ?
C14 C15 Cl1 119.3(4) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 C12 120.3(4) . . ?
C16 C17 H17 119.8 . . ?
O2 C7 C2 121.9(4) . . ?
C6 C7 O2 117.6(4) . . ?
C6 C7 C2 120.4(5) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C4 C3 C2 119.0(4) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.2(4) . . ?
C14 C13 H13 119.4 . . ?
C7 C2 C1 113.7(4) . . ?
C3 C2 C1 126.7(4) . . ?
C3 C2 C7 119.6(4) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 C15 118.7(4) . . ?
C13 C14 H14 120.6 . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C6 C5 C4 122.1(5) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.7(5) . . ?
C5 C4 H4 120.2 . . ?
C7 C6 H6 120.4 . . ?
C5 C6 C7 119.3(5) . . ?
C5 C6 H6 120.4 . . ?

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 C15 C14 C13 -178.6(4) . . . . ?
O1 C1 C9 C10 0.0(5) . . . . ?
O1 C1 C9 C8 179.8(4) . . . . ?
O1 C1 C2 C7 179.5(4) . . . . ?
O1 C1 C2 C3 -1.4(7) . . . . ?
O1 C11 C12 C17 3.3(5) . . . . ?
O1 C11 C12 C13 -177.0(4) . . . . ?
O1 C11 C10 C9 0.6(5) . . . . ?
O2 C7 C2 C1 0.1(6) . . . . ?
O2 C7 C2 C3 -179.1(4) . . . . ?
O2 C7 C6 C5 179.9(4) . . . . ?
C1 O1 C11 C12 179.1(3) . . . . ?
C1 O1 C11 C10 -0.5(5) . . . . ?
C1 C9 C8 O2 1.1(6) . . . . ?
C1 C9 C8 O3 -177.9(5) . . . . ?
C11 O1 C1 C9 0.3(4) . . . . ?
C11 O1 C1 C2 -179.5(4) . . . . ?
C11 C12 C17 C16 -179.7(4) . . . . ?
C11 C12 C13 C14 -179.9(4) . . . . ?
C11 C10 C9 C1 -0.4(5) . . . . ?
C11 C10 C9 C8 179.9(5) . . . . ?
C12 C11 C10 C9 -179.0(4) . . . . ?
C12 C13 C14 C15 -0.6(7) . . . . ?
C10 C11 C12 C17 -177.1(5) . . . . ?
C10 C11 C12 C13 2.5(7) . . . . ?
C10 C9 C8 O2 -179.1(5) . . . . ?
C10 C9 C8 O3 1.8(9) . . . . ?
C16 C15 C14 C13 1.1(7) . . . . ?
C9 C1 C2 C7 -0.3(6) . . . . ?
C9 C1 C2 C3 178.8(4) . . . . ?
C8 O2 C7 C2 0.8(6) . . . . ?
C8 O2 C7 C6 -178.7(4) . . . . ?
C15 C16 C17 C12 -0.1(7) . . . . ?
C17 C12 C13 C14 -0.2(7) . . . . ?
C17 C16 C15 Cl1 179.0(3) . . . . ?
C17 C16 C15 C14 -0.8(7) . . . . ?
C7 O2 C8 O3 177.7(4) . . . . ?
C7 O2 C8 C9 -1.4(6) . . . . ?
C13 C12 C17 C16 0.6(6) . . . . ?
C2 C1 C9 C10 179.9(4) . . . . ?
C2 C1 C9 C8 -0.3(7) . . . . ?
C2 C7 C6 C5 0.4(7) . . . . ?
C2 C3 C4 C5 -0.4(7) . . . . ?
C4 C3 C2 C1 -179.5(5) . . . . ?
C4 C3 C2 C7 -0.4(6) . . . . ?
C4 C5 C6 C7 -1.3(8) . . . . ?
C6 C7 C2 C1 179.6(4) . . . . ?
C6 C7 C2 C3 0.4(7) . . . . ?
C6 C5 C4 C3 1.2(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
