# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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. 
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data_pb_26_04_138_0m
_database_code_depnum_ccdc_archive 'CCDC 2322098'
loop_
_audit_author_name
_audit_author_address
'KAMLESH SATPUTE'
;INDIAN INSTITUTE OF TECHNOLOGY ROPAR
India
;
_audit_update_record             
;
2023-12-27 deposited with the CCDC.	2024-03-25 downloaded from the CCDC.
;
_audit_creation_date             2023-12-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 O3'
_chemical_formula_sum            'C18 H20 O3'
_chemical_formula_weight         284.34
_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   33.380(12)
_cell_length_b                   5.972(3)
_cell_length_c                   18.656(7)
_cell_angle_alpha                90
_cell_angle_beta                 119.978(11)
_cell_angle_gamma                90
_cell_volume                     3222(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3275
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      3.4
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs-2016/2
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'Plate Type'
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.045
_exptl_transmission_factor_max   0.7454
_exptl_transmission_factor_min   0.6106
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17379
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.431
_diffrn_reflns_theta_min         3.449
_diffrn_ambient_temperature      298.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2527
_reflns_number_total             3275
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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         0.718
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3275
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0790
_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)+(0.1251P)²+3.8445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2235
_refine_ls_wR_factor_ref         0.2399
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C17(H17), C16(H16), C15(H15), C14(H14), C5(H5), C4(H4), C3(H3),
 C2(H2), C1(H1)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C11(H11A,H11B,H11C)
;
_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
O3 O 0.40302(6) 1.0507(3) 0.36108(10) 0.0475(5) Uani 1 1 d . . . . .
O1 O 0.50129(12) 0.3915(6) 0.4051(3) 0.1545(18) Uani 1 1 d . U . . .
O2 O 0.53310(10) 0.6299(7) 0.3597(2) 0.1267(13) Uani 1 1 d . . . . .
C18 C 0.31019(9) 0.9362(5) 0.32534(16) 0.0532(7) Uani 1 1 d . . . . .
H18 H 0.311609 1.072755 0.302768 0.064 Uiso 1 1 calc R U . . .
C17 C 0.27380(10) 0.8943(6) 0.33864(19) 0.0675(9) Uani 1 1 d . . . . .
H17 H 0.250905 1.001647 0.324806 0.081 Uiso 1 1 calc R U . . .
C16 C 0.27143(12) 0.6940(7) 0.3723(2) 0.0739(10) Uani 1 1 d . . . . .
H16 H 0.247130 0.665854 0.381980 0.089 Uiso 1 1 calc R U . . .
C15 C 0.30460(13) 0.5375(6) 0.3914(2) 0.0759(10) Uani 1 1 d . . . . .
H15 H 0.302772 0.401501 0.413959 0.091 Uiso 1 1 calc R U . . .
C14 C 0.34157(11) 0.5771(5) 0.37786(18) 0.0598(8) Uani 1 1 d . . . . .
H14 H 0.363950 0.467282 0.391057 0.072 Uiso 1 1 calc R U . . .
C13 C 0.34498(8) 0.7778(4) 0.34503(13) 0.0406(6) Uani 1 1 d . . . . .
C7 C 0.38357(7) 0.8362(4) 0.32553(13) 0.0381(6) Uani 1 1 d . . . . .
C12 C 0.42515(10) 1.0645(5) 0.44893(16) 0.0630(8) Uani 1 1 d . . . . .
H12A H 0.436418 1.213928 0.466339 0.094 Uiso 1 1 calc R U . . .
H12B H 0.450577 0.961192 0.473174 0.094 Uiso 1 1 calc R U . . .
H12C H 0.403384 1.027553 0.466475 0.094 Uiso 1 1 calc R U . . .
C6 C 0.36119(7) 0.8652(4) 0.23189(13) 0.0373(6) Uani 1 1 d . . . . .
C5 C 0.36660(9) 1.0579(4) 0.19598(16) 0.0518(7) Uani 1 1 d . . . . .
H5 H 0.384874 1.174528 0.229332 0.062 Uiso 1 1 calc R U . . .
C4 C 0.34489(11) 1.0772(5) 0.11062(18) 0.0626(8) Uani 1 1 d . . . . .
H4 H 0.348558 1.207684 0.087285 0.075 Uiso 1 1 calc R U . . .
C3 C 0.31794(10) 0.9063(5) 0.05976(16) 0.0616(8) Uani 1 1 d . . . . .
H3 H 0.303374 0.920787 0.002540 0.074 Uiso 1 1 calc R U . . .
C2 C 0.31295(9) 0.7138(5) 0.09501(16) 0.0578(8) Uani 1 1 d . . . . .
H2 H 0.295042 0.596812 0.061356 0.069 Uiso 1 1 calc R U . . .
C1 C 0.33431(8) 0.6928(4) 0.17994(15) 0.0460(6) Uani 1 1 d . . . . .
H1 H 0.330659 0.561374 0.202786 0.055 Uiso 1 1 calc R U . . .
C8 C 0.42196(8) 0.6578(4) 0.35566(15) 0.0459(6) Uani 1 1 d . . . . .
H8A H 0.434348 0.632545 0.414378 0.055 Uiso 1 1 calc R U . . .
H8B H 0.408712 0.517972 0.327122 0.055 Uiso 1 1 calc R U . . .
C9 C 0.46116(9) 0.7258(5) 0.34078(18) 0.0610(8) Uani 1 1 d . . . . .
H9A H 0.448626 0.752732 0.282127 0.073 Uiso 1 1 calc R U . . .
H9B H 0.474499 0.864996 0.369719 0.073 Uiso 1 1 calc R U . . .
C10 C 0.49816(10) 0.5551(7) 0.3686(2) 0.0729(10) Uani 1 1 d . . . . .
C11 C 0.57043(17) 0.4688(14) 0.3814(4) 0.169(3) Uani 1 1 d . . . . .
H11A H 0.590791 0.523942 0.362937 0.253 Uiso 1 1 calc R U . . .
H11B H 0.557578 0.328003 0.355085 0.253 Uiso 1 1 calc R U . . .
H11C H 0.587434 0.448850 0.440287 0.253 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
O3 C7 1.440(3) . ?
O3 C12 1.424(3) . ?
O1 C10 1.165(5) . ?
O2 C10 1.335(5) . ?
O2 C11 1.462(6) . ?
C18 H18 0.9300 . ?
C18 C17 1.379(4) . ?
C18 C13 1.397(3) . ?
C17 H17 0.9300 . ?
C17 C16 1.372(5) . ?
C16 H16 0.9300 . ?
C16 C15 1.354(5) . ?
C15 H15 0.9300 . ?
C15 C14 1.399(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.377(4) . ?
C13 C7 1.543(3) . ?
C7 C6 1.528(3) . ?
C7 C8 1.540(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C6 C5 1.388(3) . ?
C6 C1 1.391(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.386(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.378(4) . ?
C3 H3 0.9300 . ?
C3 C2 1.375(4) . ?
C2 H2 0.9300 . ?
C2 C1 1.380(4) . ?
C1 H1 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.522(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.481(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
C12 O3 C7 115.90(19) . . ?
C10 O2 C11 115.0(4) . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C13 121.4(3) . . ?
C13 C18 H18 119.3 . . ?
C18 C17 H17 120.1 . . ?
C16 C17 C18 119.9(3) . . ?
C16 C17 H17 120.1 . . ?
C17 C16 H16 120.1 . . ?
C15 C16 C17 119.8(3) . . ?
C15 C16 H16 120.1 . . ?
C16 C15 H15 119.5 . . ?
C16 C15 C14 121.0(3) . . ?
C14 C15 H15 119.5 . . ?
C15 C14 H14 119.8 . . ?
C13 C14 C15 120.3(3) . . ?
C13 C14 H14 119.8 . . ?
C18 C13 C7 117.9(2) . . ?
C14 C13 C18 117.6(2) . . ?
C14 C13 C7 124.5(2) . . ?
O3 C7 C13 109.25(17) . . ?
O3 C7 C6 106.04(17) . . ?
O3 C7 C8 110.24(18) . . ?
C6 C7 C13 107.83(17) . . ?
C6 C7 C8 109.75(18) . . ?
C8 C7 C13 113.44(19) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C6 C7 122.6(2) . . ?
C5 C6 C1 118.1(2) . . ?
C1 C6 C7 119.3(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 119.9 . . ?
C5 C4 H4 119.5 . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 H4 119.5 . . ?
C4 C3 H3 120.5 . . ?
C2 C3 C4 118.9(2) . . ?
C2 C3 H3 120.5 . . ?
C3 C2 H2 119.7 . . ?
C3 C2 C1 120.6(3) . . ?
C1 C2 H2 119.7 . . ?
C6 C1 H1 119.5 . . ?
C2 C1 C6 121.1(2) . . ?
C2 C1 H1 119.5 . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 C7 112.5(2) . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 C8 113.2(3) . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
O1 C10 O2 121.6(3) . . ?
O1 C10 C9 126.7(3) . . ?
O2 C10 C9 110.7(3) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
O3 C7 C6 C5 8.2(3) . . . . ?
O3 C7 C6 C1 -171.89(19) . . . . ?
O3 C7 C8 C9 -53.4(3) . . . . ?
C18 C17 C16 C15 -0.8(5) . . . . ?
C18 C13 C7 O3 52.2(3) . . . . ?
C18 C13 C7 C6 -62.6(3) . . . . ?
C18 C13 C7 C8 175.7(2) . . . . ?
C17 C18 C13 C14 0.4(4) . . . . ?
C17 C18 C13 C7 178.2(2) . . . . ?
C17 C16 C15 C14 0.4(5) . . . . ?
C16 C15 C14 C13 0.4(5) . . . . ?
C15 C14 C13 C18 -0.7(4) . . . . ?
C15 C14 C13 C7 -178.4(3) . . . . ?
C14 C13 C7 O3 -130.2(2) . . . . ?
C14 C13 C7 C6 115.0(3) . . . . ?
C14 C13 C7 C8 -6.7(3) . . . . ?
C13 C18 C17 C16 0.4(4) . . . . ?
C13 C7 C6 C5 125.1(2) . . . . ?
C13 C7 C6 C1 -55.0(3) . . . . ?
C13 C7 C8 C9 -176.3(2) . . . . ?
C7 C6 C5 C4 -178.9(2) . . . . ?
C7 C6 C1 C2 179.0(2) . . . . ?
C7 C8 C9 C10 -179.4(2) . . . . ?
C12 O3 C7 C13 62.8(2) . . . . ?
C12 O3 C7 C6 178.8(2) . . . . ?
C12 O3 C7 C8 -62.5(3) . . . . ?
C6 C7 C8 C9 63.0(3) . . . . ?
C6 C5 C4 C3 -0.6(4) . . . . ?
C5 C6 C1 C2 -1.0(4) . . . . ?
C5 C4 C3 C2 -0.3(5) . . . . ?
C4 C3 C2 C1 0.5(4) . . . . ?
C3 C2 C1 C6 0.2(4) . . . . ?
C1 C6 C5 C4 1.2(4) . . . . ?
C8 C7 C6 C5 -110.9(2) . . . . ?
C8 C7 C6 C1 69.1(3) . . . . ?
C8 C9 C10 O1 -6.6(6) . . . . ?
C8 C9 C10 O2 -175.5(3) . . . . ?
C11 O2 C10 O1 13.5(7) . . . . ?
C11 O2 C10 C9 -176.9(4) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.426 0.750 21.8 0.2 ?
2 0.000 0.574 0.250 21.8 0.2 ?
3 0.500 0.074 0.250 21.8 0.2 ?
4 0.500 -0.074 0.750 21.8 0.2 ?

_olex2_submission_special_instructions 'No special instructions were received'
