# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2284012'
loop_
_audit_author_name
_audit_author_address
'Dr. Shobhana Krishnaswamy'
;IIT Madras
India
;
_audit_update_record             
;
2023-07-24 deposited with the CCDC.	2023-10-09 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         ?
_chemical_formula_sum            'C18 H12 O3'
_chemical_formula_weight         276.28

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.4483(3)
_cell_length_b                   12.3287(4)
_cell_length_c                   13.9849(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.347(2)
_cell_angle_gamma                90
_cell_volume                     1282.01(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6779
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      25.28

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6950
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS-2016/2 - Bruker AXS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture Diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22014
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.739
_diffrn_reflns_theta_max         25.363
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2342
_reflns_number_gt                1840
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX4(Bruker, 2021)'
_computing_cell_refinement       'APEX4/SAINT (Bruker, 2021)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019), WinGX'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  ?
_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)+(0.0506P)²+0.3573P] 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_number_reflns         2342
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1142
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
C1 C 0.1972(2) 0.68354(13) 0.48306(13) 0.0466(4) Uani 1 1 d . . . . .
C2 C 0.1795(2) 0.61495(12) 0.56627(11) 0.0373(4) Uani 1 1 d . . . . .
C3 C 0.1265(2) 0.66140(13) 0.65113(12) 0.0441(4) Uani 1 1 d . . . . .
H3 H 0.101488 0.735255 0.652702 0.053 Uiso 1 1 calc R U . . .
C4 C 0.1106(2) 0.60059(14) 0.73215(12) 0.0444(4) Uani 1 1 d . . . . .
H4 H 0.077572 0.632891 0.788595 0.053 Uiso 1 1 calc R U . . .
C5 C 0.1447(2) 0.48935(14) 0.72868(12) 0.0406(4) Uani 1 1 d . . . . .
C6 C 0.1947(2) 0.44157(13) 0.64450(11) 0.0388(4) Uani 1 1 d . . . . .
H6 H 0.214570 0.367139 0.642829 0.047 Uiso 1 1 calc R U . . .
C7 C 0.21551(18) 0.50293(12) 0.56270(11) 0.0334(4) Uani 1 1 d . . . . .
C8 C 0.27194(18) 0.45775(12) 0.47275(11) 0.0333(4) Uani 1 1 d . . . . .
C9 C 0.3134(2) 0.34632(13) 0.45946(12) 0.0408(4) Uani 1 1 d . . . . .
H9 H 0.305063 0.298443 0.510401 0.049 Uiso 1 1 calc R U . . .
C10 C 0.3646(2) 0.30836(13) 0.37445(12) 0.0443(4) Uani 1 1 d . . . . .
H10 H 0.391783 0.235161 0.368330 0.053 Uiso 1 1 calc R U . . .
C11 C 0.3775(2) 0.37803(13) 0.29457(11) 0.0386(4) Uani 1 1 d . . . . .
C12 C 0.4280(2) 0.34098(15) 0.20450(12) 0.0486(4) Uani 1 1 d . . . . .
H12 H 0.457184 0.268276 0.196820 0.058 Uiso 1 1 calc R U . . .
C13 C 0.4347(3) 0.40991(17) 0.12853(13) 0.0552(5) Uani 1 1 d . . . . .
H13 H 0.468180 0.383946 0.069715 0.066 Uiso 1 1 calc R U . . .
C14 C 0.3915(3) 0.51943(16) 0.13877(13) 0.0546(5) Uani 1 1 d . . . . .
H14 H 0.394702 0.565705 0.086382 0.065 Uiso 1 1 calc R U . . .
C15 C 0.3448(2) 0.55908(14) 0.22490(12) 0.0456(4) Uani 1 1 d . . . . .
H15 H 0.318011 0.632338 0.231005 0.055 Uiso 1 1 calc R U . . .
C16 C 0.33683(19) 0.48964(13) 0.30494(11) 0.0360(4) Uani 1 1 d . . . . .
C17 C 0.28609(19) 0.52567(12) 0.39580(11) 0.0347(4) Uani 1 1 d . . . . .
C18 C 0.0993(3) 0.46500(17) 0.89551(13) 0.0589(5) Uani 1 1 d . . . . .
H18A H 0.195441 0.513566 0.914831 0.088 Uiso 1 1 calc R U . . .
H18B H 0.093783 0.407413 0.941452 0.088 Uiso 1 1 calc R U . . .
H18C H -0.012509 0.503923 0.891959 0.088 Uiso 1 1 calc R U . . .
O1 O 0.1696(2) 0.77978(10) 0.47867(10) 0.0776(5) Uani 1 1 d . . . . .
O2 O 0.25130(16) 0.63560(8) 0.40113(8) 0.0451(3) Uani 1 1 d . . . . .
O3 O 0.13092(18) 0.42045(10) 0.80359(9) 0.0557(4) Uani 1 1 d . . . . .


_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
C1 O1 1.205(2) . ?
C1 O2 1.370(2) . ?
C1 C2 1.451(2) . ?
C2 C3 1.395(2) . ?
C2 C7 1.408(2) . ?
C3 C4 1.370(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(2) . ?
C4 H4 0.9300 . ?
C5 O3 1.357(2) . ?
C5 C6 1.387(2) . ?
C6 C7 1.388(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.460(2) . ?
C8 C17 1.372(2) . ?
C8 C9 1.423(2) . ?
C9 C10 1.353(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.417(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.411(2) . ?
C11 C16 1.418(2) . ?
C12 C13 1.364(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.397(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.364(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.413(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.418(2) . ?
C17 O2 1.3827(18) . ?
C18 O3 1.430(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
O1 C1 O2 116.07(16) . . ?
O1 C1 C2 126.27(17) . . ?
O2 C1 C2 117.66(14) . . ?
C3 C2 C7 119.77(15) . . ?
C3 C2 C1 119.11(14) . . ?
C7 C2 C1 121.12(14) . . ?
C4 C3 C2 121.43(15) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 118.96(15) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
O3 C5 C6 115.18(14) . . ?
O3 C5 C4 124.46(15) . . ?
C6 C5 C4 120.35(15) . . ?
C5 C6 C7 121.11(15) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C2 118.34(14) . . ?
C6 C7 C8 123.64(13) . . ?
C2 C7 C8 118.01(14) . . ?
C17 C8 C9 117.36(14) . . ?
C17 C8 C7 118.82(13) . . ?
C9 C8 C7 123.82(14) . . ?
C10 C9 C8 121.55(15) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 121.25(15) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 122.78(15) . . ?
C12 C11 C16 118.36(15) . . ?
C10 C11 C16 118.87(14) . . ?
C13 C12 C11 121.16(17) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 120.21(17) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 120.60(17) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 120.47(17) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 123.08(15) . . ?
C15 C16 C11 119.18(15) . . ?
C17 C16 C11 117.73(14) . . ?
C8 C17 O2 122.18(14) . . ?
C8 C17 C16 123.25(14) . . ?
O2 C17 C16 114.58(13) . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 O2 C17 122.20(12) . . ?
C5 O3 C18 118.51(14) . . ?

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 C1 C2 C3 -0.3(3) . . . . ?
O2 C1 C2 C3 179.35(14) . . . . ?
O1 C1 C2 C7 179.93(18) . . . . ?
O2 C1 C2 C7 -0.4(2) . . . . ?
C7 C2 C3 C4 0.8(2) . . . . ?
C1 C2 C3 C4 -178.94(15) . . . . ?
C2 C3 C4 C5 -1.4(2) . . . . ?
C3 C4 C5 O3 -179.02(15) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
O3 C5 C6 C7 -179.32(14) . . . . ?
C4 C5 C6 C7 1.3(2) . . . . ?
C5 C6 C7 C2 -1.8(2) . . . . ?
C5 C6 C7 C8 178.50(14) . . . . ?
C3 C2 C7 C6 0.8(2) . . . . ?
C1 C2 C7 C6 -179.48(14) . . . . ?
C3 C2 C7 C8 -179.53(13) . . . . ?
C1 C2 C7 C8 0.2(2) . . . . ?
C6 C7 C8 C17 179.19(14) . . . . ?
C2 C7 C8 C17 -0.5(2) . . . . ?
C6 C7 C8 C9 -0.7(2) . . . . ?
C2 C7 C8 C9 179.65(14) . . . . ?
C17 C8 C9 C10 -0.1(2) . . . . ?
C7 C8 C9 C10 179.78(15) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
C9 C10 C11 C12 -179.08(16) . . . . ?
C9 C10 C11 C16 0.4(2) . . . . ?
C10 C11 C12 C13 178.36(16) . . . . ?
C16 C11 C12 C13 -1.1(2) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 1.0(3) . . . . ?
C13 C14 C15 C16 -0.9(3) . . . . ?
C14 C15 C16 C17 -178.85(15) . . . . ?
C14 C15 C16 C11 -0.2(2) . . . . ?
C12 C11 C16 C15 1.2(2) . . . . ?
C10 C11 C16 C15 -178.33(14) . . . . ?
C12 C11 C16 C17 179.92(13) . . . . ?
C10 C11 C16 C17 0.4(2) . . . . ?
C9 C8 C17 O2 -179.15(13) . . . . ?
C7 C8 C17 O2 1.0(2) . . . . ?
C9 C8 C17 C16 0.9(2) . . . . ?
C7 C8 C17 C16 -178.92(13) . . . . ?
C15 C16 C17 C8 177.58(14) . . . . ?
C11 C16 C17 C8 -1.1(2) . . . . ?
C15 C16 C17 O2 -2.3(2) . . . . ?
C11 C16 C17 O2 178.98(13) . . . . ?
O1 C1 O2 C17 -179.42(16) . . . . ?
C2 C1 O2 C17 0.9(2) . . . . ?
C8 C17 O2 C1 -1.2(2) . . . . ?
C16 C17 O2 C1 178.69(14) . . . . ?
C6 C5 O3 C18 173.26(15) . . . . ?
C4 C5 O3 C18 -7.4(2) . . . . ?

_refine_diff_density_max         0.154
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2284013'
loop_
_audit_author_name
_audit_author_address
'Dr. Shobhana Krishnaswamy'
;IIT Madras
India
;
_audit_update_record             
;
2023-07-24 deposited with the CCDC.	2023-10-09 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         ?
_chemical_formula_sum            'C18 H10 O4'
_chemical_formula_weight         290.26

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.6565(5)
_cell_length_b                   9.0691(5)
_cell_length_c                   10.0037(5)
_cell_angle_alpha                79.041(2)
_cell_angle_beta                 70.617(2)
_cell_angle_gamma                62.258(2)
_cell_volume                     655.09(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7092
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      25.63

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_F_000             300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.264
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7051
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'SADABS-2016/2 - Bruker AXS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture Diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21364
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.998
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2479
_reflns_number_gt                1965
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX4(Bruker, 2021)'
_computing_cell_refinement       'APEX4/SAINT (Bruker, 2021)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  ?
_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)+(0.0450P)²+0.1728P] 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_number_reflns         2479
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0924
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
C1 C 0.7209(3) 0.8305(2) 0.40723(18) 0.0500(5) Uani 1 1 d . . . . .
H1A H 0.648818 0.912036 0.347632 0.060 Uiso 1 1 calc R U . . .
H1B H 0.777388 0.881501 0.440458 0.060 Uiso 1 1 calc R U . . .
C2 C 0.8340(2) 0.5531(2) 0.40515(17) 0.0413(4) Uani 1 1 d . . . . .
C3 C 0.9330(2) 0.3899(2) 0.36855(19) 0.0505(5) Uani 1 1 d . . . . .
H3 H 1.033102 0.356819 0.289009 0.061 Uiso 1 1 calc R U . . .
C4 C 0.8755(2) 0.2773(2) 0.45676(19) 0.0473(4) Uani 1 1 d . . . . .
H4 H 0.935627 0.165688 0.434182 0.057 Uiso 1 1 calc R U . . .
C5 C 0.7301(2) 0.32664(19) 0.57837(17) 0.0382(4) Uani 1 1 d . . . . .
C6 C 0.6649(2) 0.2025(2) 0.65251(18) 0.0434(4) Uani 1 1 d . . . . .
C7 C 0.4211(2) 0.41402(19) 0.80932(16) 0.0362(4) Uani 1 1 d . . . . .
C8 C 0.2688(2) 0.4381(2) 0.92627(18) 0.0455(4) Uani 1 1 d . . . . .
H8 H 0.224956 0.357648 0.954088 0.055 Uiso 1 1 calc R U . . .
C9 C 0.1863(2) 0.5789(2) 0.99826(18) 0.0461(4) Uani 1 1 d . . . . .
H9 H 0.080832 0.598299 1.072369 0.055 Uiso 1 1 calc R U . . .
C10 C 0.2585(2) 0.6977(2) 0.96222(16) 0.0384(4) Uani 1 1 d . . . . .
C11 C 0.1831(2) 0.8359(2) 1.04687(18) 0.0485(4) Uani 1 1 d . . . . .
H11 H 0.080235 0.852724 1.123119 0.058 Uiso 1 1 calc R U . . .
C12 C 0.2577(3) 0.9451(2) 1.01921(19) 0.0523(5) Uani 1 1 d . . . . .
H12 H 0.204153 1.037691 1.074008 0.063 Uiso 1 1 calc R U . . .
C13 C 0.4160(3) 0.9167(2) 0.90739(18) 0.0476(4) Uani 1 1 d . . . . .
H13 H 0.469778 0.988967 0.890389 0.057 Uiso 1 1 calc R U . . .
C14 C 0.4928(2) 0.7844(2) 0.82278(16) 0.0390(4) Uani 1 1 d . . . . .
H14 H 0.599271 0.767292 0.750313 0.047 Uiso 1 1 calc R U . . .
C15 C 0.4140(2) 0.67285(18) 0.84299(15) 0.0324(3) Uani 1 1 d . . . . .
C16 C 0.4892(2) 0.53060(18) 0.75727(15) 0.0319(3) Uani 1 1 d . . . . .
C17 C 0.6350(2) 0.49446(18) 0.62263(15) 0.0322(3) Uani 1 1 d . . . . .
C18 C 0.6884(2) 0.60527(19) 0.52565(16) 0.0352(4) Uani 1 1 d . . . . .
O1 O 0.60817(17) 0.77635(14) 0.52488(11) 0.0471(3) Uani 1 1 d . . . . .
O2 O 0.85663(18) 0.68705(16) 0.32894(12) 0.0554(4) Uani 1 1 d . . . . .
O3 O 0.7372(2) 0.05581(15) 0.63040(15) 0.0621(4) Uani 1 1 d . . . . .
O4 O 0.49827(16) 0.26082(14) 0.75023(13) 0.0450(3) Uani 1 1 d . . . . .


_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
C1 O2 1.428(2) . ?
C1 O1 1.429(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 O2 1.366(2) . ?
C2 C3 1.370(2) . ?
C2 C18 1.385(2) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(2) . ?
C4 H4 0.9300 . ?
C5 C17 1.428(2) . ?
C5 C6 1.461(2) . ?
C6 O3 1.206(2) . ?
C6 O4 1.366(2) . ?
C7 C16 1.380(2) . ?
C7 O4 1.3829(19) . ?
C7 C8 1.400(2) . ?
C8 C9 1.348(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.418(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.411(2) . ?
C10 C15 1.428(2) . ?
C11 C12 1.359(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.400(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.366(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.415(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.446(2) . ?
C16 C17 1.473(2) . ?
C17 C18 1.389(2) . ?
C18 O1 1.3732(18) . ?

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
O2 C1 O1 107.46(13) . . ?
O2 C1 H1A 110.2 . . ?
O1 C1 H1A 110.2 . . ?
O2 C1 H1B 110.2 . . ?
O1 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
O2 C2 C3 126.46(15) . . ?
O2 C2 C18 110.24(14) . . ?
C3 C2 C18 123.26(16) . . ?
C2 C3 C4 116.07(15) . . ?
C2 C3 H3 122.0 . . ?
C4 C3 H3 122.0 . . ?
C3 C4 C5 121.65(16) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C17 122.47(16) . . ?
C4 C5 C6 116.83(15) . . ?
C17 C5 C6 120.40(15) . . ?
O3 C6 O4 116.53(16) . . ?
O3 C6 C5 126.89(17) . . ?
O4 C6 C5 116.41(14) . . ?
C16 C7 O4 122.77(14) . . ?
C16 C7 C8 123.78(15) . . ?
O4 C7 C8 113.45(14) . . ?
C9 C8 C7 119.47(15) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 120.74(16) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 120.53(15) . . ?
C11 C10 C15 119.79(15) . . ?
C9 C10 C15 119.62(15) . . ?
C12 C11 C10 121.31(17) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 119.31(16) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 121.07(17) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 121.46(16) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C10 116.86(14) . . ?
C14 C15 C16 123.99(14) . . ?
C10 C15 C16 118.99(14) . . ?
C7 C16 C15 116.57(14) . . ?
C7 C16 C17 116.61(13) . . ?
C15 C16 C17 126.79(13) . . ?
C18 C17 C5 113.75(14) . . ?
C18 C17 C16 128.41(14) . . ?
C5 C17 C16 117.73(14) . . ?
O1 C18 C2 108.92(13) . . ?
O1 C18 C17 128.58(14) . . ?
C2 C18 C17 122.41(14) . . ?
C18 O1 C1 106.59(12) . . ?
C2 O2 C1 106.30(12) . . ?
C6 O4 C7 121.85(13) . . ?

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 C2 C3 C4 -174.81(17) . . . . ?
C18 C2 C3 C4 2.4(3) . . . . ?
C2 C3 C4 C5 -2.5(3) . . . . ?
C3 C4 C5 C17 -2.2(3) . . . . ?
C3 C4 C5 C6 171.57(16) . . . . ?
C4 C5 C6 O3 10.1(3) . . . . ?
C17 C5 C6 O3 -176.04(17) . . . . ?
C4 C5 C6 O4 -164.91(14) . . . . ?
C17 C5 C6 O4 9.0(2) . . . . ?
C16 C7 C8 C9 -3.2(3) . . . . ?
O4 C7 C8 C9 176.62(15) . . . . ?
C7 C8 C9 C10 -3.9(3) . . . . ?
C8 C9 C10 C11 -173.30(16) . . . . ?
C8 C9 C10 C15 3.8(2) . . . . ?
C9 C10 C11 C12 175.72(16) . . . . ?
C15 C10 C11 C12 -1.4(3) . . . . ?
C10 C11 C12 C13 -2.1(3) . . . . ?
C11 C12 C13 C14 2.3(3) . . . . ?
C12 C13 C14 C15 1.2(3) . . . . ?
C13 C14 C15 C10 -4.5(2) . . . . ?
C13 C14 C15 C16 -179.82(14) . . . . ?
C11 C10 C15 C14 4.6(2) . . . . ?
C9 C10 C15 C14 -172.52(15) . . . . ?
C11 C10 C15 C16 -179.86(14) . . . . ?
C9 C10 C15 C16 3.0(2) . . . . ?
O4 C7 C16 C15 -170.06(13) . . . . ?
C8 C7 C16 C15 9.8(2) . . . . ?
O4 C7 C16 C17 8.0(2) . . . . ?
C8 C7 C16 C17 -172.18(14) . . . . ?
C14 C15 C16 C7 165.81(14) . . . . ?
C10 C15 C16 C7 -9.4(2) . . . . ?
C14 C15 C16 C17 -12.0(2) . . . . ?
C10 C15 C16 C17 172.82(13) . . . . ?
C4 C5 C17 C18 6.5(2) . . . . ?
C6 C5 C17 C18 -166.97(14) . . . . ?
C4 C5 C17 C16 -176.87(14) . . . . ?
C6 C5 C17 C16 9.6(2) . . . . ?
C7 C16 C17 C18 158.16(15) . . . . ?
C15 C16 C17 C18 -24.0(2) . . . . ?
C7 C16 C17 C5 -17.86(19) . . . . ?
C15 C16 C17 C5 159.94(14) . . . . ?
O2 C2 C18 O1 3.24(18) . . . . ?
C3 C2 C18 O1 -174.36(16) . . . . ?
O2 C2 C18 C17 -179.92(14) . . . . ?
C3 C2 C18 C17 2.5(3) . . . . ?
C5 C17 C18 O1 169.52(15) . . . . ?
C16 C17 C18 O1 -6.6(3) . . . . ?
C5 C17 C18 C2 -6.7(2) . . . . ?
C16 C17 C18 C2 177.20(15) . . . . ?
C2 C18 O1 C1 -6.41(18) . . . . ?
C17 C18 O1 C1 177.01(16) . . . . ?
O2 C1 O1 C18 7.19(18) . . . . ?
C3 C2 O2 C1 178.87(18) . . . . ?
C18 C2 O2 C1 1.36(19) . . . . ?
O1 C1 O2 C2 -5.25(19) . . . . ?
O3 C6 O4 C7 164.50(15) . . . . ?
C5 C6 O4 C7 -20.0(2) . . . . ?
C16 C7 O4 C6 11.8(2) . . . . ?
C8 C7 O4 C6 -168.10(14) . . . . ?

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
C1 H1B O3 0.97 2.53 3.375(2) 145.0 1_565 yes

_refine_diff_density_max         0.160
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.036

