# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
# 
#######################################################################

data_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc2kdwmh
_database_code_depnum_ccdc_archive 'CCDC 2365877'
loop_
_audit_author_name
_audit_author_address
'Alex Andrews'
;Indian Institute of Science Education and Research Thiruvananthapuram, Kerala
India
;
_audit_update_record             
;
2024-06-26 deposited with the CCDC.	2024-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 O5'
_chemical_formula_sum            'C15 H18 O5'
_chemical_formula_weight         278.29

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.3959(5)
_cell_length_b                   10.1952(7)
_cell_length_c                   18.4363(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1390.15(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4184
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      24.73

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.330
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.095
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            15831
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.283
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2441
_reflns_number_gt                2094
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.706
_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.
 
 _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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Br uker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP3- 2014.1(Farrugia, 1997) '
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0597P)²+0.1823P] 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 775 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(5)
_chemical_absolute_configuration RM
_refine_ls_number_reflns         2441
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.1061
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.4244(4) 0.5416(3) 0.51671(16) 0.0412(7) Uani 1 1 d . . . . .
C2 C 0.4749(4) 0.4617(3) 0.46012(16) 0.0389(7) Uani 1 1 d . . . . .
C3 C 0.3500(4) 0.3764(3) 0.42609(15) 0.0350(6) Uani 1 1 d . . . . .
C4 C 0.1720(4) 0.3726(3) 0.45202(14) 0.0343(6) Uani 1 1 d . . . . .
C5 C 0.1218(4) 0.4502(3) 0.51074(15) 0.0393(7) Uani 1 1 d . . . . .
H5 H 0.004253 0.446498 0.528523 0.047 Uiso 1 1 calc R U . . .
C6 C 0.2461(4) 0.5323(3) 0.54241(16) 0.0409(7) Uani 1 1 d . . . . .
C7 C 0.4001(4) 0.2950(3) 0.36453(16) 0.0418(7) Uani 1 1 d . . . . .
C8 C 0.0889(4) 0.2198(3) 0.35848(16) 0.0398(7) Uani 1 1 d . . . . .
C9 C 0.0423(4) 0.2909(3) 0.41564(15) 0.0382(7) Uani 1 1 d . . . . .
H9 H -0.076124 0.287969 0.432471 0.046 Uiso 1 1 calc R U . . .
C10 C 0.0412(5) 0.5966(4) 0.6362(2) 0.0658(10) Uani 1 1 d . . . . .
H10A H 0.035245 0.656401 0.676371 0.099 Uiso 1 1 calc R U . . .
H10B H -0.053840 0.616217 0.602483 0.099 Uiso 1 1 calc R U . . .
H10C H 0.027346 0.508365 0.653596 0.099 Uiso 1 1 calc R U . . .
C11 C 0.5562(5) 0.6335(4) 0.5518(2) 0.0617(9) Uani 1 1 d . . . . .
H11A H 0.496748 0.680785 0.590013 0.093 Uiso 1 1 calc R U . . .
H11B H 0.655215 0.584234 0.571615 0.093 Uiso 1 1 calc R U . . .
H11C H 0.600941 0.694244 0.516339 0.093 Uiso 1 1 calc R U . . .
C12 C 0.6980(5) 0.5460(4) 0.3814(2) 0.0645(10) Uani 1 1 d . . . . .
H12A H 0.824868 0.539185 0.370971 0.097 Uiso 1 1 calc R U . . .
H12B H 0.629779 0.521345 0.339219 0.097 Uiso 1 1 calc R U . . .
H12C H 0.669416 0.634745 0.394401 0.097 Uiso 1 1 calc R U . . .
C13 C -0.0285(4) 0.1378(3) 0.31225(17) 0.0454(7) Uani 1 1 d . . . . .
H13A H -0.142046 0.123242 0.337306 0.054 Uiso 1 1 calc R U . . .
H13B H 0.028841 0.053106 0.305536 0.054 Uiso 1 1 calc R U . . .
C14 C -0.0681(4) 0.1965(3) 0.23832(15) 0.0434(7) Uani 1 1 d . . . . .
H14 H 0.047106 0.205479 0.212549 0.052 Uiso 1 1 calc R U . . .
C15 C -0.1868(5) 0.1061(3) 0.19458(18) 0.0589(9) Uani 1 1 d . . . . .
H15A H -0.131041 0.021261 0.191423 0.088 Uiso 1 1 calc R U . . .
H15B H -0.302526 0.098092 0.217744 0.088 Uiso 1 1 calc R U . . .
H15C H -0.202449 0.141350 0.146705 0.088 Uiso 1 1 calc R U . . .
O1 O 0.2107(3) 0.6094(2) 0.60121(12) 0.0526(6) Uani 1 1 d . . . . .
O2 O 0.6536(3) 0.4610(2) 0.43993(12) 0.0508(6) Uani 1 1 d . . . . .
O3 O 0.5460(3) 0.2834(3) 0.33663(14) 0.0676(7) Uani 1 1 d . . . . .
O4 O 0.2655(3) 0.2205(2) 0.33375(11) 0.0473(6) Uani 1 1 d . . . . .
O5 O -0.1458(3) 0.3236(2) 0.24437(12) 0.0535(6) Uani 1 1 d . . . . .
H5A H -0.236033 0.320021 0.270167 0.080 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
C1 C2 1.375(4) . ?
C1 C6 1.405(4) . ?
C1 C11 1.499(4) . ?
C2 O2 1.373(3) . ?
C2 C3 1.415(4) . ?
C3 C4 1.401(4) . ?
C3 C7 1.454(4) . ?
C4 C5 1.391(4) . ?
C4 C9 1.436(4) . ?
C5 C6 1.374(4) . ?
C6 O1 1.364(4) . ?
C7 O3 1.201(3) . ?
C7 O4 1.374(4) . ?
C8 C9 1.325(4) . ?
C8 O4 1.384(3) . ?
C8 C13 1.476(4) . ?
C10 O1 1.416(4) . ?
C12 O2 1.423(4) . ?
C13 C14 1.517(4) . ?
C14 O5 1.422(4) . ?
C14 C15 1.507(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
C2 C1 C6 118.1(3) . . ?
C2 C1 C11 121.4(3) . . ?
C6 C1 C11 120.4(3) . . ?
O2 C2 C1 118.1(3) . . ?
O2 C2 C3 120.3(3) . . ?
C1 C2 C3 121.5(3) . . ?
C4 C3 C2 118.6(3) . . ?
C4 C3 C7 119.3(3) . . ?
C2 C3 C7 122.0(3) . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 C9 121.0(2) . . ?
C3 C4 C9 118.9(3) . . ?
C6 C5 C4 119.9(3) . . ?
O1 C6 C5 124.1(3) . . ?
O1 C6 C1 114.2(3) . . ?
C5 C6 C1 121.7(3) . . ?
O3 C7 O4 114.8(3) . . ?
O3 C7 C3 128.2(3) . . ?
O4 C7 C3 116.9(2) . . ?
C9 C8 O4 120.3(3) . . ?
C9 C8 C13 128.1(3) . . ?
O4 C8 C13 111.6(2) . . ?
C8 C9 C4 121.0(3) . . ?
C8 C13 C14 114.2(2) . . ?
O5 C14 C15 111.3(3) . . ?
O5 C14 C13 111.5(2) . . ?
C15 C14 C13 110.6(3) . . ?
C6 O1 C10 118.6(3) . . ?
C2 O2 C12 115.1(3) . . ?
C7 O4 C8 123.4(2) . . ?

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
C6 C1 C2 O2 -173.4(3) . . . . ?
C11 C1 C2 O2 4.8(4) . . . . ?
C6 C1 C2 C3 2.8(4) . . . . ?
C11 C1 C2 C3 -179.0(3) . . . . ?
O2 C2 C3 C4 175.1(2) . . . . ?
C1 C2 C3 C4 -1.1(4) . . . . ?
O2 C2 C3 C7 -6.1(4) . . . . ?
C1 C2 C3 C7 177.7(3) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C7 C3 C4 C5 -179.8(2) . . . . ?
C2 C3 C4 C9 177.1(2) . . . . ?
C7 C3 C4 C9 -1.7(4) . . . . ?
C3 C4 C5 C6 1.2(4) . . . . ?
C9 C4 C5 C6 -176.8(3) . . . . ?
C4 C5 C6 O1 -178.3(3) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
C2 C1 C6 O1 176.4(2) . . . . ?
C11 C1 C6 O1 -1.9(4) . . . . ?
C2 C1 C6 C5 -2.6(4) . . . . ?
C11 C1 C6 C5 179.2(3) . . . . ?
C4 C3 C7 O3 -177.9(3) . . . . ?
C2 C3 C7 O3 3.3(5) . . . . ?
C4 C3 C7 O4 1.8(4) . . . . ?
C2 C3 C7 O4 -177.0(2) . . . . ?
O4 C8 C9 C4 1.6(4) . . . . ?
C13 C8 C9 C4 -175.8(3) . . . . ?
C5 C4 C9 C8 178.1(3) . . . . ?
C3 C4 C9 C8 0.1(4) . . . . ?
C9 C8 C13 C14 105.9(4) . . . . ?
O4 C8 C13 C14 -71.7(3) . . . . ?
C8 C13 C14 O5 -56.1(4) . . . . ?
C8 C13 C14 C15 179.4(3) . . . . ?
C5 C6 O1 C10 5.8(4) . . . . ?
C1 C6 O1 C10 -173.1(3) . . . . ?
C1 C2 O2 C12 -95.6(3) . . . . ?
C3 C2 O2 C12 88.1(3) . . . . ?
O3 C7 O4 C8 179.6(3) . . . . ?
C3 C7 O4 C8 -0.1(4) . . . . ?
C9 C8 O4 C7 -1.6(4) . . . . ?
C13 C8 O4 C7 176.2(2) . . . . ?

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
C12 H12B O3 0.96 2.50 3.018(5) 113.5 . yes
C12 H12C O1 0.96 2.63 3.529(4) 156.6 4_566 yes
C13 H13B O5 0.97 2.66 3.607(4) 165.9 3_545 yes
O5 H5A O3 0.82 2.06 2.873(3) 171.9 1_455 yes

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.032



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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 2365878'
loop_
_audit_author_name
_audit_author_address
'Alex Andrews'
;Indian Institute of Science Education and Research Thiruvananthapuram, Kerala
India
;
_audit_update_record             
;
2024-06-26 deposited with the CCDC.	2024-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 O5'
_chemical_formula_sum            'C15 H18 O5'
_chemical_formula_weight         278.29

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.4075(3)
_cell_length_b                   10.2397(5)
_cell_length_c                   18.5058(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1403.68(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9932
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      27.36

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.317
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.095
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.068
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.994
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            33358
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_av_R_equivalents  0.0894
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.201
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2464
_reflns_number_gt                2020
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.705
_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.
 
 _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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Br uker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP3- 2014.1(Farrugia, 1997) '
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0594P)²] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.047(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 725 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(4)
_chemical_absolute_configuration RM
_refine_ls_number_reflns         2464
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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 0.7541(3) 0.5321(3) 0.54289(14) 0.0471(6) Uani 1 1 d . . . . .
C2 C 0.5762(3) 0.5412(3) 0.51669(14) 0.0483(7) Uani 1 1 d . . . . .
C3 C 0.5257(3) 0.4619(3) 0.45992(15) 0.0468(6) Uani 1 1 d . . . . .
C4 C 0.6500(3) 0.3767(3) 0.42574(13) 0.0425(6) Uani 1 1 d . . . . .
C5 C 0.8281(3) 0.3733(2) 0.45212(13) 0.0413(6) Uani 1 1 d . . . . .
C6 C 0.8779(3) 0.4501(3) 0.51106(13) 0.0454(6) Uani 1 1 d . . . . .
H6 H 0.995127 0.445858 0.528918 0.054 Uiso 1 1 calc R U . . .
C7 C 0.9580(3) 0.2914(3) 0.41522(14) 0.0470(7) Uani 1 1 d . . . . .
H7 H 1.076509 0.288310 0.431768 0.056 Uiso 1 1 calc R U . . .
C8 C 0.9113(3) 0.2208(3) 0.35849(14) 0.0458(6) Uani 1 1 d . . . . .
C9 C 0.6007(3) 0.2954(3) 0.36421(15) 0.0506(7) Uani 1 1 d . . . . .
C10 C 1.0285(4) 0.1385(3) 0.31256(16) 0.0536(7) Uani 1 1 d . . . . .
H10A H 0.970832 0.054298 0.305893 0.064 Uiso 1 1 calc R U . . .
H10B H 1.141655 0.123741 0.337644 0.064 Uiso 1 1 calc R U . . .
C11 C 1.0688(3) 0.1967(3) 0.23886(13) 0.0513(7) Uani 1 1 d . . . . .
H11 H 0.953671 0.205538 0.213222 0.062 Uiso 1 1 calc R U . . .
C12 C 1.1863(4) 0.1072(3) 0.19513(17) 0.0696(9) Uani 1 1 d . . . . .
H12A H 1.203422 0.143385 0.147766 0.104 Uiso 1 1 calc R U . . .
H12B H 1.129467 0.023275 0.191160 0.104 Uiso 1 1 calc R U . . .
H12C H 1.301286 0.097753 0.218506 0.104 Uiso 1 1 calc R U . . .
C13 C 0.9588(4) 0.5954(4) 0.63659(19) 0.0783(10) Uani 1 1 d . . . . .
H13A H 0.977591 0.505574 0.649504 0.117 Uiso 1 1 calc R U . . .
H13B H 0.959400 0.648184 0.679446 0.117 Uiso 1 1 calc R U . . .
H13C H 1.053716 0.623452 0.604856 0.117 Uiso 1 1 calc R U . . .
C14 C 0.4436(4) 0.6340(3) 0.55164(18) 0.0734(9) Uani 1 1 d . . . . .
H14A H 0.333796 0.635512 0.524089 0.110 Uiso 1 1 calc R U . . .
H14B H 0.494624 0.720137 0.553061 0.110 Uiso 1 1 calc R U . . .
H14C H 0.418163 0.605258 0.599954 0.110 Uiso 1 1 calc R U . . .
C15 C 0.3018(4) 0.5461(3) 0.38069(19) 0.0739(10) Uani 1 1 d . . . . .
H15A H 0.328720 0.634759 0.393624 0.111 Uiso 1 1 calc R U . . .
H15B H 0.175431 0.538208 0.370019 0.111 Uiso 1 1 calc R U . . .
H15C H 0.370997 0.521936 0.338919 0.111 Uiso 1 1 calc R U . . .
O1 O 0.7893(2) 0.6085(2) 0.60091(11) 0.0618(6) Uani 1 1 d . . . . .
O2 O 0.3468(2) 0.4617(2) 0.43952(11) 0.0606(6) Uani 1 1 d . . . . .
O3 O 0.4549(2) 0.2841(2) 0.33632(12) 0.0759(7) Uani 1 1 d . . . . .
O4 O 0.7351(2) 0.22195(18) 0.33377(10) 0.0561(5) Uani 1 1 d . . . . .
O5 O 1.1462(2) 0.32402(18) 0.24449(10) 0.0621(6) Uani 1 1 d . . . . .
H5 H 1.234171 0.321385 0.271337 0.093 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
C1 O1 1.354(3) . ?
C1 C6 1.376(3) . ?
C1 C2 1.408(3) . ?
C2 C3 1.379(4) . ?
C2 C14 1.512(4) . ?
C3 O2 1.378(3) . ?
C3 C4 1.418(4) . ?
C4 C5 1.408(3) . ?
C4 C9 1.457(4) . ?
C5 C6 1.394(3) . ?
C5 C7 1.448(3) . ?
C7 C8 1.320(4) . ?
C8 O4 1.383(3) . ?
C8 C10 1.479(3) . ?
C9 O3 1.203(3) . ?
C9 O4 1.369(3) . ?
C10 C11 1.518(4) . ?
C11 O5 1.428(3) . ?
C11 C12 1.501(4) . ?
C13 O1 1.425(3) . ?
C15 O2 1.429(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
O1 C1 C6 124.3(2) . . ?
O1 C1 C2 114.5(2) . . ?
C6 C1 C2 121.2(2) . . ?
C3 C2 C1 118.5(2) . . ?
C3 C2 C14 121.3(2) . . ?
C1 C2 C14 120.2(2) . . ?
O2 C3 C2 118.0(2) . . ?
O2 C3 C4 120.1(2) . . ?
C2 C3 C4 121.8(2) . . ?
C5 C4 C3 118.0(2) . . ?
C5 C4 C9 119.5(2) . . ?
C3 C4 C9 122.5(2) . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 C7 121.3(2) . . ?
C4 C5 C7 118.3(2) . . ?
C1 C6 C5 120.2(2) . . ?
C8 C7 C5 121.2(2) . . ?
C7 C8 O4 120.4(2) . . ?
C7 C8 C10 127.9(2) . . ?
O4 C8 C10 111.6(2) . . ?
O3 C9 O4 115.1(2) . . ?
O3 C9 C4 128.0(2) . . ?
O4 C9 C4 116.96(19) . . ?
C8 C10 C11 114.1(2) . . ?
O5 C11 C12 111.3(2) . . ?
O5 C11 C10 111.8(2) . . ?
C12 C11 C10 111.0(2) . . ?
C1 O1 C13 118.8(2) . . ?
C3 O2 C15 115.6(2) . . ?
C9 O4 C8 123.69(19) . . ?

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 -176.8(2) . . . . ?
C6 C1 C2 C3 2.6(4) . . . . ?
O1 C1 C2 C14 1.8(4) . . . . ?
C6 C1 C2 C14 -178.8(2) . . . . ?
C1 C2 C3 O2 173.4(2) . . . . ?
C14 C2 C3 O2 -5.1(4) . . . . ?
C1 C2 C3 C4 -2.8(4) . . . . ?
C14 C2 C3 C4 178.6(3) . . . . ?
O2 C3 C4 C5 -175.3(2) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
O2 C3 C4 C9 5.9(4) . . . . ?
C2 C3 C4 C9 -177.9(2) . . . . ?
C3 C4 C5 C6 1.3(4) . . . . ?
C9 C4 C5 C6 -179.8(2) . . . . ?
C3 C4 C5 C7 -177.0(2) . . . . ?
C9 C4 C5 C7 1.9(3) . . . . ?
O1 C1 C6 C5 178.9(2) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
C4 C5 C6 C1 -1.5(4) . . . . ?
C7 C5 C6 C1 176.7(2) . . . . ?
C6 C5 C7 C8 -178.6(2) . . . . ?
C4 C5 C7 C8 -0.3(4) . . . . ?
C5 C7 C8 O4 -1.2(4) . . . . ?
C5 C7 C8 C10 176.3(2) . . . . ?
C5 C4 C9 O3 178.0(3) . . . . ?
C3 C4 C9 O3 -3.2(5) . . . . ?
C5 C4 C9 O4 -1.9(3) . . . . ?
C3 C4 C9 O4 176.9(2) . . . . ?
C7 C8 C10 C11 -105.9(3) . . . . ?
O4 C8 C10 C11 71.8(3) . . . . ?
C8 C10 C11 O5 55.6(3) . . . . ?
C8 C10 C11 C12 -179.3(2) . . . . ?
C6 C1 O1 C13 -6.5(4) . . . . ?
C2 C1 O1 C13 172.9(3) . . . . ?
C2 C3 O2 C15 96.1(3) . . . . ?
C4 C3 O2 C15 -87.6(3) . . . . ?
O3 C9 O4 C8 -179.5(3) . . . . ?
C4 C9 O4 C8 0.4(4) . . . . ?
C7 C8 O4 C9 1.2(4) . . . . ?
C10 C8 O4 C9 -176.7(2) . . . . ?

_refine_diff_density_max         0.220
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.070



