# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_mo_gs_ps_a_o_284_0m
_database_code_depnum_ccdc_archive 'CCDC 2350807'
loop_
_audit_author_name
_audit_author_address
'pradip sanjay w'
;IITH
India
;
_audit_update_record             
;
2024-04-24 deposited with the CCDC.	2025-06-05 downloaded from the CCDC.
;
_audit_creation_date             2021-11-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 O2'
_chemical_formula_sum            'C21 H14 O2'
_chemical_formula_weight         298.32
_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'
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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   11.0954(7)
_cell_length_b                   15.8197(9)
_cell_length_c                   17.3494(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3045.3(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5054
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      23.99
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1628 before and 0.0622 after correction.
The Ratio of minimum to maximum transmission is 0.8919.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            27887
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.138
_diffrn_reflns_theta_min         2.531
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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                2021
_reflns_number_total             3365
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+0.2481P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1111
_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:
 C12(H12), C11(H11), C17(H17), C18(H18), C19(H19), C14(H14), C13(H13), C3(H3),
 C8(H8), C7(H7), C6(H6), C5(H5), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O2 O 0.74237(10) 0.62246(6) 0.41083(6) 0.0532(3) Uani 1 1 d . . . . .
O1 O 0.84924(11) 0.69606(8) 0.52857(7) 0.0746(4) Uani 1 1 d . . . . .
C12 C 0.8316(2) 0.36918(12) 0.39469(10) 0.0745(6) Uani 1 1 d . . . . .
H12 H 0.852181 0.312333 0.391035 0.089 Uiso 1 1 calc R U . . .
C11 C 0.71507(19) 0.39423(11) 0.38056(9) 0.0639(5) Uani 1 1 d . . . . .
H11 H 0.657887 0.353869 0.367098 0.077 Uiso 1 1 calc R U . . .
C10 C 0.68039(16) 0.47941(10) 0.38600(8) 0.0508(4) Uani 1 1 d . . . . .
C15 C 0.77009(16) 0.53629(10) 0.40671(8) 0.0515(4) Uani 1 1 d . . . . .
C2 C 0.67244(15) 0.64144(9) 0.47543(8) 0.0455(4) Uani 1 1 d . . . . .
C1 C 0.73969(15) 0.68990(9) 0.53476(9) 0.0486(4) Uani 1 1 d . . . . .
C16 C 0.67841(13) 0.72907(9) 0.60233(8) 0.0436(4) Uani 1 1 d . . . . .
C17 C 0.56525(14) 0.76559(9) 0.59939(9) 0.0507(4) Uani 1 1 d . . . . .
H17 H 0.521986 0.765640 0.553477 0.061 Uiso 1 1 calc R U . . .
C18 C 0.51644(16) 0.80207(11) 0.66488(10) 0.0617(5) Uani 1 1 d . . . . .
H18 H 0.439864 0.825886 0.662924 0.074 Uiso 1 1 calc R U . . .
C19 C 0.5802(2) 0.80335(11) 0.73268(11) 0.0696(5) Uani 1 1 d . . . . .
H19 H 0.546399 0.827216 0.776628 0.084 Uiso 1 1 calc R U . . .
C14 C 0.88727(18) 0.51196(12) 0.42072(10) 0.0656(5) Uani 1 1 d . . . . .
H14 H 0.945137 0.551755 0.434404 0.079 Uiso 1 1 calc R U . . .
C13 C 0.9175(2) 0.42754(13) 0.41412(11) 0.0770(6) Uani 1 1 d . . . . .
H13 H 0.996503 0.410316 0.422901 0.092 Uiso 1 1 calc R U . . .
C3 C 0.55885(14) 0.61497(9) 0.47905(8) 0.0456(4) Uani 1 1 d . . . . .
H3 H 0.515294 0.628788 0.523086 0.055 Uiso 1 1 calc R U . . .
C4 C 0.49643(15) 0.56588(9) 0.41958(8) 0.0471(4) Uani 1 1 d . . . . .
C9 C 0.55464(15) 0.50575(9) 0.37247(8) 0.0506(4) Uani 1 1 d . . . . .
C8 C 0.4863(2) 0.46566(11) 0.31536(10) 0.0649(5) Uani 1 1 d . . . . .
H8 H 0.523383 0.426646 0.283044 0.078 Uiso 1 1 calc R U . . .
C7 C 0.3659(2) 0.48247(12) 0.30586(11) 0.0761(6) Uani 1 1 d . . . . .
H7 H 0.322978 0.455794 0.266754 0.091 Uiso 1 1 calc R U . . .
C6 C 0.30828(19) 0.53863(12) 0.35394(12) 0.0744(6) Uani 1 1 d . . . . .
H6 H 0.226248 0.548990 0.348291 0.089 Uiso 1 1 calc R U . . .
C5 C 0.37322(16) 0.57939(10) 0.41053(10) 0.0600(5) Uani 1 1 d . . . . .
H5 H 0.333900 0.616746 0.443408 0.072 Uiso 1 1 calc R U . . .
C20 C 0.69367(19) 0.76948(11) 0.73553(10) 0.0668(5) Uani 1 1 d . . . . .
H20 H 0.737582 0.771573 0.781149 0.080 Uiso 1 1 calc R U . . .
C21 C 0.74287(16) 0.73239(10) 0.67117(9) 0.0555(4) Uani 1 1 d . . . . .
H21 H 0.819863 0.709309 0.673596 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
O2 C15 1.3992(18) . ?
O2 C2 1.3957(17) . ?
O1 C1 1.2242(18) . ?
C12 H12 0.9300 . ?
C12 C11 1.374(3) . ?
C12 C13 1.370(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.405(2) . ?
C10 C15 1.389(2) . ?
C10 C9 1.475(2) . ?
C15 C14 1.378(2) . ?
C2 C1 1.485(2) . ?
C2 C3 1.330(2) . ?
C1 C16 1.490(2) . ?
C16 C17 1.383(2) . ?
C16 C21 1.393(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.373(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.369(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.382(3) . ?
C13 H13 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.465(2) . ?
C4 C9 1.411(2) . ?
C4 C5 1.392(2) . ?
C9 C8 1.400(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.372(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.376(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.378(2) . ?
C5 H5 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.374(2) . ?
C21 H21 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
C2 O2 C15 111.89(11) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C13 C12 C11 120.30(18) . . ?
C12 C11 H11 119.3 . . ?
C12 C11 C10 121.50(18) . . ?
C10 C11 H11 119.3 . . ?
C11 C10 C9 121.30(16) . . ?
C15 C10 C11 116.27(17) . . ?
C15 C10 C9 122.41(14) . . ?
C10 C15 O2 119.13(15) . . ?
C14 C15 O2 118.07(15) . . ?
C14 C15 C10 122.75(16) . . ?
O2 C2 C1 112.86(13) . . ?
C3 C2 O2 119.82(14) . . ?
C3 C2 C1 127.32(14) . . ?
O1 C1 C2 118.64(14) . . ?
O1 C1 C16 119.28(14) . . ?
C2 C1 C16 122.06(14) . . ?
C17 C16 C1 123.99(14) . . ?
C17 C16 C21 118.81(15) . . ?
C21 C16 C1 117.12(14) . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 119.93(16) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.50(17) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 119.95(17) . . ?
C20 C19 H19 120.0 . . ?
C15 C14 H14 120.5 . . ?
C15 C14 C13 119.00(19) . . ?
C13 C14 H14 120.5 . . ?
C12 C13 C14 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C2 C3 H3 117.2 . . ?
C2 C3 C4 125.56(14) . . ?
C4 C3 H3 117.2 . . ?
C9 C4 C3 123.29(15) . . ?
C5 C4 C3 117.51(14) . . ?
C5 C4 C9 119.19(15) . . ?
C4 C9 C10 122.11(14) . . ?
C8 C9 C10 119.82(15) . . ?
C8 C9 C4 117.87(16) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 C9 121.66(17) . . ?
C7 C8 H8 119.2 . . ?
C8 C7 H7 119.9 . . ?
C8 C7 C6 120.30(17) . . ?
C6 C7 H7 119.9 . . ?
C7 C6 H6 120.3 . . ?
C7 C6 C5 119.42(19) . . ?
C5 C6 H6 120.3 . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.45(17) . . ?
C6 C5 H5 119.3 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.19(17) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.58(17) . . ?
C20 C21 H21 119.7 . . ?

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
O2 C15 C14 C13 -177.61(14) . . . . ?
O2 C2 C1 O1 -11.8(2) . . . . ?
O2 C2 C1 C16 169.79(12) . . . . ?
O2 C2 C3 C4 -0.1(2) . . . . ?
O1 C1 C16 C17 144.88(16) . . . . ?
O1 C1 C16 C21 -31.7(2) . . . . ?
C12 C11 C10 C15 -0.3(2) . . . . ?
C12 C11 C10 C9 -178.62(15) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C11 C10 C15 O2 178.05(12) . . . . ?
C11 C10 C15 C14 0.6(2) . . . . ?
C11 C10 C9 C4 137.68(15) . . . . ?
C11 C10 C9 C8 -37.0(2) . . . . ?
C10 C15 C14 C13 -0.1(2) . . . . ?
C10 C9 C8 C7 173.63(15) . . . . ?
C15 O2 C2 C1 109.34(14) . . . . ?
C15 O2 C2 C3 -69.54(18) . . . . ?
C15 C10 C9 C4 -40.5(2) . . . . ?
C15 C10 C9 C8 144.79(15) . . . . ?
C15 C14 C13 C12 -0.7(3) . . . . ?
C2 O2 C15 C10 73.31(17) . . . . ?
C2 O2 C15 C14 -109.09(16) . . . . ?
C2 C1 C16 C17 -36.8(2) . . . . ?
C2 C1 C16 C21 146.64(14) . . . . ?
C2 C3 C4 C9 33.3(2) . . . . ?
C2 C3 C4 C5 -147.46(15) . . . . ?
C1 C2 C3 C4 -178.85(13) . . . . ?
C1 C16 C17 C18 -178.66(14) . . . . ?
C1 C16 C21 C20 178.34(14) . . . . ?
C16 C17 C18 C19 0.9(3) . . . . ?
C17 C16 C21 C20 1.6(2) . . . . ?
C17 C18 C19 C20 1.0(3) . . . . ?
C18 C19 C20 C21 -1.5(3) . . . . ?
C19 C20 C21 C16 0.3(3) . . . . ?
C13 C12 C11 C10 -0.4(3) . . . . ?
C3 C2 C1 O1 166.93(15) . . . . ?
C3 C2 C1 C16 -11.4(2) . . . . ?
C3 C4 C9 C10 8.0(2) . . . . ?
C3 C4 C9 C8 -177.19(14) . . . . ?
C3 C4 C5 C6 177.27(15) . . . . ?
C4 C9 C8 C7 -1.3(2) . . . . ?
C9 C10 C15 O2 -3.7(2) . . . . ?
C9 C10 C15 C14 178.86(14) . . . . ?
C9 C4 C5 C6 -3.5(2) . . . . ?
C9 C8 C7 C6 -1.3(3) . . . . ?
C8 C7 C6 C5 1.6(3) . . . . ?
C7 C6 C5 C4 0.9(3) . . . . ?
C5 C4 C9 C10 -171.18(14) . . . . ?
C5 C4 C9 C8 3.6(2) . . . . ?
C21 C16 C17 C18 -2.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
