# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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. 
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data_mo_gs_ds_2_469_0m
_database_code_depnum_ccdc_archive 'CCDC 2245703'
loop_
_audit_author_name
_audit_author_address
'Mr Dasari Srinivas'
;IIT Hyderabad
India
;
_audit_update_record             
;
2023-03-02 deposited with the CCDC.	2023-05-12 downloaded from the CCDC.
;
_audit_creation_date             2023-01-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 O5'
_chemical_formula_sum            'C18 H18 O5'
_chemical_formula_weight         314.32
_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                   8.8205(4)
_cell_length_b                   18.7330(11)
_cell_length_c                   19.9045(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3288.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6999
_cell_measurement_temperature    297
_cell_measurement_theta_max      24.83
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0907 before and 0.0606 after correction.
The Ratio of minimum to maximum transmission is 0.9011.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.214
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            27161
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.442
_diffrn_reflns_theta_min         2.046
_diffrn_ambient_temperature      297
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_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                2501
_reflns_number_total             3692
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3692
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0524
_refine_ls_restrained_S_all      1.034
_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)+(0.0708P)²+1.0737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1580
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3A), C6(H6), C13(H13), C14(H14), C17(H17)
2.b Tetrahedral OH refined with riding coordinates:
 O4(H4)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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
O1 O 0.65924(18) 0.09983(9) 0.53906(7) 0.0689(5) Uani 1 1 d . . . . .
O2 O 0.29604(16) 0.37378(9) 0.62013(7) 0.0630(4) Uani 1 1 d . . . . .
O3 O 0.41160(17) 0.41335(9) 0.52842(7) 0.0634(4) Uani 1 1 d . . . . .
H3 H 0.325772 0.408280 0.513326 0.095 Uiso 1 1 calc R U . . .
O4 O 0.55505(19) 0.15293(10) 0.45235(8) 0.0786(5) Uani 1 1 d . . . . .
H4 H 0.557371 0.118906 0.426458 0.118 Uiso 1 1 calc R U . . .
C1 C 0.7468(3) 0.48967(12) 0.66404(12) 0.0677(6) Uani 1 1 d . . . . .
H1 H 0.792298 0.534368 0.661354 0.081 Uiso 1 1 calc R U . . .
C2 C 0.8017(3) 0.43885(12) 0.70798(12) 0.0679(6) Uani 1 1 d . . . . .
H2 H 0.883719 0.449571 0.735575 0.081 Uiso 1 1 calc R U . . .
C3 C 0.7357(3) 0.37239(11) 0.71111(10) 0.0563(5) Uani 1 1 d . . . . .
H3A H 0.775190 0.338574 0.740499 0.068 Uiso 1 1 calc R U . . .
C4 C 0.6116(2) 0.35439(9) 0.67157(8) 0.0416(4) Uani 1 1 d . . . . .
C5 C 0.5470(2) 0.28089(9) 0.67426(9) 0.0419(4) Uani 1 1 d . . . . .
C6 C 0.5229(2) 0.24838(10) 0.73632(9) 0.0502(5) Uani 1 1 d . . . . .
H6 H 0.549264 0.271870 0.775789 0.060 Uiso 1 1 calc R U . . .
C7 C 0.4598(3) 0.18124(11) 0.73876(10) 0.0588(5) Uani 1 1 d . . . . .
O8 O 0.4294(3) 0.14554(10) 0.79725(8) 0.0919(6) Uani 1 1 d . . . . .
C9 C 0.4465(4) 0.18265(17) 0.85785(12) 0.0960(10) Uani 1 1 d . . . . .
H9A H 0.388351 0.225931 0.856260 0.144 Uiso 1 1 calc R U . . .
H9B H 0.551584 0.194010 0.864520 0.144 Uiso 1 1 calc R U . . .
H9C H 0.411386 0.153460 0.894298 0.144 Uiso 1 1 calc R U . . .
C10 C 0.5479(2) 0.13084(9) 0.51097(9) 0.0457(4) Uani 1 1 d . . . . .
C11 C 0.4038(2) 0.13976(10) 0.55178(10) 0.0512(5) Uani 1 1 d . . . . .
C12 C 0.4462(2) 0.17609(9) 0.61831(9) 0.0454(4) Uani 1 1 d . . . . .
C13 C 0.4210(3) 0.14524(11) 0.68017(10) 0.0569(5) Uani 1 1 d . . . . .
H13 H 0.377803 0.100040 0.682730 0.068 Uiso 1 1 calc R U . . .
C14 C 0.6238(3) 0.47335(11) 0.62421(10) 0.0581(5) Uani 1 1 d . . . . .
H14 H 0.587098 0.507220 0.594166 0.070 Uiso 1 1 calc R U . . .
C15 C 0.5538(2) 0.40705(9) 0.62829(9) 0.0436(4) Uani 1 1 d . . . . .
C16 C 0.4127(2) 0.39687(9) 0.58914(9) 0.0448(4) Uani 1 1 d . . . . .
C17 C 0.5110(2) 0.24398(9) 0.61625(9) 0.0424(4) Uani 1 1 d . . . . .
H17 H 0.530541 0.264961 0.574801 0.051 Uiso 1 1 calc R U . . .
C18 C 0.3377(3) 0.06459(13) 0.56150(13) 0.0776(7) Uani 1 1 d . . . . .
H18A H 0.316952 0.043720 0.518420 0.116 Uiso 1 1 calc R U . . .
H18B H 0.245457 0.067646 0.586921 0.116 Uiso 1 1 calc R U . . .
H18C H 0.409453 0.035438 0.585219 0.116 Uiso 1 1 calc R U . . .
C19 C 0.2895(2) 0.18550(14) 0.51252(12) 0.0680(6) Uani 1 1 d . . . . .
H19A H 0.332706 0.231615 0.503806 0.102 Uiso 1 1 calc R U . . .
H19B H 0.198562 0.190943 0.538508 0.102 Uiso 1 1 calc R U . . .
H19C H 0.265870 0.162508 0.470704 0.102 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 C10 1.270(2) . ?
O2 C16 1.275(2) . ?
O3 H3 0.8200 . ?
O3 C16 1.247(2) . ?
O4 H4 0.8200 . ?
O4 C10 1.240(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.380(3) . ?
C1 C14 1.378(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(3) . ?
C3 H3A 0.9300 . ?
C3 C4 1.390(3) . ?
C4 C5 1.491(2) . ?
C4 C15 1.405(2) . ?
C5 C6 1.394(2) . ?
C5 C17 1.383(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.376(3) . ?
C7 O8 1.369(2) . ?
C7 C13 1.390(3) . ?
O8 C9 1.400(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.518(3) . ?
C11 C12 1.535(3) . ?
C11 C18 1.536(3) . ?
C11 C19 1.537(3) . ?
C12 C13 1.378(3) . ?
C12 C17 1.395(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.390(3) . ?
C15 C16 1.481(3) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C16 O3 H3 109.5 . . ?
C10 O4 H4 109.5 . . ?
C2 C1 H1 120.4 . . ?
C14 C1 H1 120.4 . . ?
C14 C1 C2 119.2(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3A 119.1 . . ?
C2 C3 C4 121.83(19) . . ?
C4 C3 H3A 119.1 . . ?
C3 C4 C5 120.30(16) . . ?
C3 C4 C15 117.55(17) . . ?
C15 C4 C5 122.13(16) . . ?
C6 C5 C4 119.59(16) . . ?
C17 C5 C4 121.30(15) . . ?
C17 C5 C6 119.12(17) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.50(18) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C13 120.88(17) . . ?
O8 C7 C6 123.75(19) . . ?
O8 C7 C13 115.36(18) . . ?
C7 O8 C9 117.96(19) . . ?
O8 C9 H9A 109.5 . . ?
O8 C9 H9B 109.5 . . ?
O8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 C11 117.52(17) . . ?
O4 C10 O1 121.87(18) . . ?
O4 C10 C11 120.61(18) . . ?
C10 C11 C12 107.84(15) . . ?
C10 C11 C18 106.51(17) . . ?
C10 C11 C19 109.79(17) . . ?
C12 C11 C18 112.97(17) . . ?
C12 C11 C19 110.57(16) . . ?
C18 C11 C19 109.04(19) . . ?
C13 C12 C11 123.06(17) . . ?
C13 C12 C17 118.32(17) . . ?
C17 C12 C11 118.61(16) . . ?
C7 C13 H13 119.8 . . ?
C12 C13 C7 120.44(18) . . ?
C12 C13 H13 119.8 . . ?
C1 C14 H14 119.5 . . ?
C1 C14 C15 120.97(19) . . ?
C15 C14 H14 119.5 . . ?
C4 C15 C16 122.48(16) . . ?
C14 C15 C4 120.13(17) . . ?
C14 C15 C16 117.27(16) . . ?
O2 C16 C15 117.86(16) . . ?
O3 C16 O2 123.13(18) . . ?
O3 C16 C15 118.96(17) . . ?
C5 C17 C12 121.70(16) . . ?
C5 C17 H17 119.1 . . ?
C12 C17 H17 119.1 . . ?
C11 C18 H18A 109.5 . . ?
C11 C18 H18B 109.5 . . ?
C11 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 C19 H19A 109.5 . . ?
C11 C19 H19B 109.5 . . ?
C11 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
O1 C10 C11 C12 53.1(2) . . . . ?
O1 C10 C11 C18 -68.4(2) . . . . ?
O1 C10 C11 C19 173.65(18) . . . . ?
O4 C10 C11 C12 -127.2(2) . . . . ?
O4 C10 C11 C18 111.2(2) . . . . ?
O4 C10 C11 C19 -6.7(3) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C1 C14 C15 C4 -2.5(3) . . . . ?
C1 C14 C15 C16 173.5(2) . . . . ?
C2 C1 C14 C15 0.7(4) . . . . ?
C2 C3 C4 C5 177.4(2) . . . . ?
C2 C3 C4 C15 -0.7(3) . . . . ?
C3 C4 C5 C6 45.7(3) . . . . ?
C3 C4 C5 C17 -134.0(2) . . . . ?
C3 C4 C15 C14 2.4(3) . . . . ?
C3 C4 C15 C16 -173.39(18) . . . . ?
C4 C5 C6 C7 178.38(18) . . . . ?
C4 C5 C17 C12 -177.95(16) . . . . ?
C4 C15 C16 O2 48.6(2) . . . . ?
C4 C15 C16 O3 -133.7(2) . . . . ?
C5 C4 C15 C14 -175.71(18) . . . . ?
C5 C4 C15 C16 8.5(3) . . . . ?
C5 C6 C7 O8 -178.8(2) . . . . ?
C5 C6 C7 C13 0.5(3) . . . . ?
C6 C5 C17 C12 2.3(3) . . . . ?
C6 C7 O8 C9 7.9(4) . . . . ?
C6 C7 C13 C12 0.5(3) . . . . ?
O8 C7 C13 C12 179.9(2) . . . . ?
C10 C11 C12 C13 -120.1(2) . . . . ?
C10 C11 C12 C17 61.0(2) . . . . ?
C11 C12 C13 C7 -179.03(19) . . . . ?
C11 C12 C17 C5 177.66(17) . . . . ?
C13 C7 O8 C9 -171.5(2) . . . . ?
C13 C12 C17 C5 -1.3(3) . . . . ?
C14 C1 C2 C3 1.0(4) . . . . ?
C14 C15 C16 O2 -127.3(2) . . . . ?
C14 C15 C16 O3 50.3(2) . . . . ?
C15 C4 C5 C6 -136.27(18) . . . . ?
C15 C4 C5 C17 44.0(3) . . . . ?
C17 C5 C6 C7 -1.9(3) . . . . ?
C17 C12 C13 C7 -0.1(3) . . . . ?
C18 C11 C12 C13 -2.6(3) . . . . ?
C18 C11 C12 C17 178.41(18) . . . . ?
C19 C11 C12 C13 119.9(2) . . . . ?
C19 C11 C12 C17 -59.1(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'Nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
