# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2457373'
loop_
_audit_author_name
_audit_author_address
'Alex Andrews'
;Indian Institute of Science Education and Research Thiruvananthapuram, Kerala
India
;
_audit_update_record             
;
2025-06-07 deposited with the CCDC.	2025-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H26 O4'
_chemical_formula_sum            'C19 H26 O4'
_chemical_formula_weight         318.40

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'

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

_cell_length_a                   6.8089(3)
_cell_length_b                   15.0295(6)
_cell_length_c                   35.9980(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3683.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    5250
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      26.80

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.148
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.148
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.025
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_source_current           1.406
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON III C14'
_diffrn_detector_area_resol_mean 7.39
_diffrn_measurement_device       'Bruker D8 QUEST'
_diffrn_measurement_device_type  'Four-circle Kappa diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_reflns_number            20034
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         2.263
_diffrn_reflns_theta_max         28.297
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4542
_reflns_number_gt                3572
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       
"Bruker APEX6 v2024.9-0'(Bruker AXS Inc., 2023)"
_computing_cell_refinement       'SAINT V8.5.0.27 (Bruker AXS LLC, 2023)'
_computing_data_reduction        'SAINT V8.5.0.27 (Bruker AXS LLC, 2023)'
_computing_structure_solution    'XT, VERSION 2018/2 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1503)'
_computing_publication_material  'APEX5 v2023.9-0 (Bruker AXS Inc., 2023)'
_computing_bruker_data_scaling   
'SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction'
_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)+(0.0915P)²+0.6007P] 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_abs_structure_details 
;
 Flack x determined using 1274 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(5)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4542
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1631
_refine_ls_wR_factor_gt          0.1496
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_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
O1 O 0.3491(4) 0.49684(17) 0.71890(6) 0.0721(8) Uani 1 1 d . . . . .
H1 H 0.364520 0.533123 0.735655 0.108 Uiso 1 1 calc R U . . .
O2 O 0.5835(4) 0.64619(16) 0.71417(5) 0.0674(7) Uani 1 1 d . . . . .
H2O H 0.619710 0.698223 0.714491 0.101 Uiso 1 1 calc R U . . .
O3 O 0.5970(4) 0.91454(13) 0.55592(6) 0.0591(6) Uani 1 1 d . . . . .
H3 H 0.603935 0.936011 0.535018 0.089 Uiso 1 1 calc R U . . .
O4 O 0.6075(4) 0.90800(15) 0.48358(6) 0.0685(7) Uani 1 1 d . . . . .
C1 C 0.6049(4) 0.63962(15) 0.62637(6) 0.0353(5) Uani 1 1 d . . . . .
C2 C 0.5391(5) 0.54213(16) 0.62152(7) 0.0433(6) Uani 1 1 d . . . . .
H2 H 0.406799 0.545927 0.610918 0.052 Uiso 1 1 calc R U . . .
C3 C 0.5133(6) 0.48739(19) 0.65818(8) 0.0582(9) Uani 1 1 d . . . . .
C4 C 0.3750(6) 0.5403(2) 0.68348(8) 0.0587(8) Uani 1 1 d . . . . .
H4 H 0.246216 0.538758 0.671361 0.070 Uiso 1 1 calc R U . . .
C5 C 0.4215(6) 0.6370(2) 0.68935(8) 0.0577(8) Uani 1 1 d . . . . .
H5 H 0.307020 0.664580 0.701174 0.069 Uiso 1 1 calc R U . . .
C6 C 0.4578(5) 0.6854(2) 0.65278(7) 0.0515(7) Uani 1 1 d . . . . .
H6A H 0.505730 0.744762 0.658276 0.062 Uiso 1 1 calc R U . . .
H6B H 0.333324 0.691781 0.639937 0.062 Uiso 1 1 calc R U . . .
C7 C 0.5987(4) 0.68598(15) 0.58828(6) 0.0339(5) Uani 1 1 d . . . . .
C8 C 0.6090(4) 0.63807(16) 0.55489(6) 0.0376(5) Uani 1 1 d . . . . .
C9 C 0.6176(6) 0.53816(18) 0.55389(8) 0.0513(7) Uani 1 1 d . . . . .
H9A H 0.718037 0.519973 0.536356 0.062 Uiso 1 1 calc R U . . .
H9B H 0.492701 0.515507 0.545006 0.062 Uiso 1 1 calc R U . . .
C10 C 0.6621(6) 0.49676(18) 0.59163(8) 0.0575(9) Uani 1 1 d . . . . .
H10A H 0.632153 0.433676 0.591031 0.069 Uiso 1 1 calc R U . . .
H10B H 0.800501 0.503610 0.597303 0.069 Uiso 1 1 calc R U . . .
C11 C 0.5925(4) 0.77817(16) 0.58689(7) 0.0388(5) Uani 1 1 d . . . . .
H11 H 0.584067 0.809824 0.609025 0.047 Uiso 1 1 calc R U . . .
C12 C 0.5984(4) 0.82505(17) 0.55351(7) 0.0399(5) Uani 1 1 d . . . . .
C13 C 0.6044(4) 0.77779(17) 0.51970(7) 0.0399(5) Uani 1 1 d . . . . .
C14 C 0.6092(4) 0.68535(18) 0.52159(7) 0.0400(5) Uani 1 1 d . . . . .
H14 H 0.612830 0.653439 0.499463 0.048 Uiso 1 1 calc R U . . .
C15 C 0.8156(5) 0.6512(2) 0.64060(8) 0.0511(7) Uani 1 1 d . . . . .
H15A H 0.848793 0.713291 0.640835 0.077 Uiso 1 1 calc R U . . .
H15B H 0.904535 0.619903 0.624554 0.077 Uiso 1 1 calc R U . . .
H15C H 0.825505 0.627691 0.665327 0.077 Uiso 1 1 calc R U . . .
C16 C 0.7042(8) 0.4607(2) 0.67744(10) 0.0790(12) Uani 1 1 d . . . . .
H16A H 0.675384 0.421388 0.697735 0.119 Uiso 1 1 calc R U . . .
H16B H 0.768847 0.512975 0.686697 0.119 Uiso 1 1 calc R U . . .
H16C H 0.788350 0.431037 0.660003 0.119 Uiso 1 1 calc R U . . .
C17 C 0.4023(10) 0.4015(3) 0.64753(11) 0.110(2) Uani 1 1 d . . . . .
H17A H 0.355317 0.372722 0.669626 0.165 Uiso 1 1 calc R U . . .
H17B H 0.489511 0.362123 0.634517 0.165 Uiso 1 1 calc R U . . .
H17C H 0.293043 0.416121 0.631818 0.165 Uiso 1 1 calc R U . . .
C18 C 0.6066(4) 0.8265(2) 0.48389(8) 0.0477(6) Uani 1 1 d . . . . .
C19 C 0.6062(5) 0.7760(2) 0.44807(7) 0.0541(7) Uani 1 1 d . . . . .
H19A H 0.722073 0.739750 0.446614 0.081 Uiso 1 1 calc R U . . .
H19B H 0.604448 0.817069 0.427655 0.081 Uiso 1 1 calc R U . . .
H19C H 0.491853 0.738716 0.446963 0.081 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
O1 C4 1.443(3) . ?
O2 C5 1.426(4) . ?
O3 C12 1.348(3) . ?
O4 C18 1.225(4) . ?
C1 C15 1.534(4) . ?
C1 C7 1.539(3) . ?
C1 C2 1.542(3) . ?
C1 C6 1.543(4) . ?
C2 C10 1.525(4) . ?
C2 C3 1.565(4) . ?
C3 C16 1.527(6) . ?
C3 C4 1.532(5) . ?
C3 C17 1.545(5) . ?
C4 C5 1.503(4) . ?
C5 C6 1.524(4) . ?
C7 C11 1.387(3) . ?
C7 C8 1.403(3) . ?
C8 C14 1.394(3) . ?
C8 C9 1.503(3) . ?
C9 C10 1.525(4) . ?
C11 C12 1.393(3) . ?
C12 C13 1.410(4) . ?
C13 C14 1.391(4) . ?
C13 C18 1.482(3) . ?
C18 C19 1.496(4) . ?

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
C15 C1 C7 105.8(2) . . ?
C15 C1 C2 114.7(2) . . ?
C7 C1 C2 108.75(18) . . ?
C15 C1 C6 110.5(2) . . ?
C7 C1 C6 109.2(2) . . ?
C2 C1 C6 107.8(2) . . ?
C10 C2 C1 110.2(2) . . ?
C10 C2 C3 114.9(2) . . ?
C1 C2 C3 115.9(2) . . ?
C16 C3 C4 112.9(3) . . ?
C16 C3 C17 108.0(4) . . ?
C4 C3 C17 106.3(3) . . ?
C16 C3 C2 115.2(3) . . ?
C4 C3 C2 107.3(3) . . ?
C17 C3 C2 106.6(2) . . ?
O1 C4 C5 109.8(2) . . ?
O1 C4 C3 111.5(3) . . ?
C5 C4 C3 117.1(3) . . ?
O2 C5 C4 110.1(3) . . ?
O2 C5 C6 111.7(3) . . ?
C4 C5 C6 112.0(2) . . ?
C5 C6 C1 115.1(2) . . ?
C11 C7 C8 118.9(2) . . ?
C11 C7 C1 119.03(19) . . ?
C8 C7 C1 122.0(2) . . ?
C14 C8 C7 118.4(2) . . ?
C14 C8 C9 119.3(2) . . ?
C7 C8 C9 122.4(2) . . ?
C8 C9 C10 113.2(2) . . ?
C2 C10 C9 109.7(3) . . ?
C7 C11 C12 122.4(2) . . ?
O3 C12 C11 116.7(2) . . ?
O3 C12 C13 124.0(2) . . ?
C11 C12 C13 119.4(2) . . ?
C14 C13 C12 117.5(2) . . ?
C14 C13 C18 122.4(2) . . ?
C12 C13 C18 120.1(2) . . ?
C13 C14 C8 123.4(2) . . ?
O4 C18 C13 120.1(3) . . ?
O4 C18 C19 120.0(3) . . ?
C13 C18 C19 119.9(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
C15 C1 C2 C10 -64.2(3) . . . . ?
C7 C1 C2 C10 54.0(3) . . . . ?
C6 C1 C2 C10 172.3(2) . . . . ?
C15 C1 C2 C3 68.5(3) . . . . ?
C7 C1 C2 C3 -173.3(3) . . . . ?
C6 C1 C2 C3 -55.0(3) . . . . ?
C10 C2 C3 C16 57.3(4) . . . . ?
C1 C2 C3 C16 -73.2(4) . . . . ?
C10 C2 C3 C4 -176.1(3) . . . . ?
C1 C2 C3 C4 53.4(4) . . . . ?
C10 C2 C3 C17 -62.5(4) . . . . ?
C1 C2 C3 C17 167.0(4) . . . . ?
C16 C3 C4 O1 -49.4(4) . . . . ?
C17 C3 C4 O1 68.9(4) . . . . ?
C2 C3 C4 O1 -177.4(3) . . . . ?
C16 C3 C4 C5 78.3(4) . . . . ?
C17 C3 C4 C5 -163.4(3) . . . . ?
C2 C3 C4 C5 -49.7(4) . . . . ?
O1 C4 C5 O2 53.0(4) . . . . ?
C3 C4 C5 O2 -75.5(3) . . . . ?
O1 C4 C5 C6 177.9(3) . . . . ?
C3 C4 C5 C6 49.5(4) . . . . ?
O2 C5 C6 C1 74.1(3) . . . . ?
C4 C5 C6 C1 -49.9(4) . . . . ?
C15 C1 C6 C5 -74.1(3) . . . . ?
C7 C1 C6 C5 169.9(3) . . . . ?
C2 C1 C6 C5 51.9(3) . . . . ?
C15 C1 C7 C11 -75.9(3) . . . . ?
C2 C1 C7 C11 160.4(3) . . . . ?
C6 C1 C7 C11 43.1(3) . . . . ?
C15 C1 C7 C8 100.9(3) . . . . ?
C2 C1 C7 C8 -22.8(3) . . . . ?
C6 C1 C7 C8 -140.1(3) . . . . ?
C11 C7 C8 C14 -1.0(4) . . . . ?
C1 C7 C8 C14 -177.8(2) . . . . ?
C11 C7 C8 C9 179.6(3) . . . . ?
C1 C7 C8 C9 2.8(4) . . . . ?
C14 C8 C9 C10 167.2(3) . . . . ?
C7 C8 C9 C10 -13.5(5) . . . . ?
C1 C2 C10 C9 -67.0(3) . . . . ?
C3 C2 C10 C9 159.8(3) . . . . ?
C8 C9 C10 C2 44.4(4) . . . . ?
C8 C7 C11 C12 -0.8(4) . . . . ?
C1 C7 C11 C12 176.1(2) . . . . ?
C7 C11 C12 O3 -178.2(3) . . . . ?
C7 C11 C12 C13 2.2(4) . . . . ?
O3 C12 C13 C14 178.7(3) . . . . ?
C11 C12 C13 C14 -1.6(4) . . . . ?
O3 C12 C13 C18 -0.9(4) . . . . ?
C11 C12 C13 C18 178.7(3) . . . . ?
C12 C13 C14 C8 -0.2(4) . . . . ?
C18 C13 C14 C8 179.4(3) . . . . ?
C7 C8 C14 C13 1.5(4) . . . . ?
C9 C8 C14 C13 -179.1(3) . . . . ?
C14 C13 C18 O4 -178.0(3) . . . . ?
C12 C13 C18 O4 1.6(4) . . . . ?
C14 C13 C18 C19 2.4(4) . . . . ?
C12 C13 C18 C19 -178.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O1 0.82 2.60 3.040(5) 114.8 3_656 yes
O1 H1 O2 0.82 2.51 3.325(3) 178.7 3_656 yes
O3 H3 O4 0.82 1.90 2.607(3) 143.9 . yes
O3 H3 O4 0.82 2.44 3.023(3) 129.1 4_576 yes

_refine_diff_density_max         0.584
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.048



