# Supplementary Information (SI) for ChemComm.
# 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. 
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data_MKB_Ortho_Coupling_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2425575'
_audit_update_record             
;
2025-02-20 deposited with the CCDC.	2025-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 O5'
_chemical_formula_sum            'C1.57 H1.41 O0.39'
_chemical_formula_weight         26.54

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   13.1701(8)
_cell_length_b                   6.1476(3)
_cell_length_c                   22.2657(13)
_cell_angle_alpha                90
_cell_angle_beta                 104.251(2)
_cell_angle_gamma                90
_cell_volume                     1747.25(17)
_cell_formula_units_Z            51
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    44225
_cell_measurement_theta_min      1.735
_cell_measurement_theta_max      24.895

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41849
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.641
_diffrn_reflns_theta_max         25.068
_diffrn_reflns_theta_full        25.068
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3099
_reflns_number_gt                1779
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_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)+(0.0562P)²+1.6003P] 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-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3099
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1329
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.1863
_refine_ls_wR_factor_gt          0.1347
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.142
_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 0.73472(19) 0.0736(4) 0.42763(11) 0.0650(7) Uani 1 1 d . . . . .
O2 O 0.8222(2) -0.0715(5) 0.62986(12) 0.0784(8) Uani 1 1 d . . . . .
O3 O 0.8721(2) 0.2453(4) 0.53205(12) 0.0680(8) Uani 1 1 d . . . . .
O4 O 0.64170(17) -0.0382(4) 0.49856(11) 0.0611(7) Uani 1 1 d . . . . .
O5 O 0.78319(18) -0.2189(4) 0.48722(12) 0.0627(7) Uani 1 1 d . . . . .
C1 C 0.4533(3) 0.9934(6) 0.75969(18) 0.0582(10) Uani 1 1 d . . . . .
C2 C 0.3873(3) 1.1425(7) 0.72319(19) 0.0690(11) Uani 1 1 d . . . . .
H2 H 0.373942 1.132379 0.680278 0.083 Uiso 1 1 calc R U . . .
C3 C 0.3413(3) 1.3050(7) 0.7493(2) 0.0796(12) Uani 1 1 d . . . . .
H3 H 0.296828 1.403924 0.724156 0.095 Uiso 1 1 calc R U . . .
C4 C 0.3608(4) 1.3217(8) 0.8124(2) 0.0861(14) Uani 1 1 d . . . . .
H4 H 0.330318 1.432925 0.830169 0.103 Uiso 1 1 calc R U . . .
C5 C 0.4250(4) 1.1750(9) 0.8490(2) 0.0953(15) Uani 1 1 d . . . . .
H5 H 0.437509 1.186148 0.891867 0.114 Uiso 1 1 calc R U . . .
C6 C 0.4719(3) 1.0098(8) 0.8234(2) 0.0811(13) Uani 1 1 d . . . . .
H6 H 0.515666 0.910407 0.848846 0.097 Uiso 1 1 calc R U . . .
C7 C 0.5050(3) 0.8284(7) 0.73225(17) 0.0630(10) Uani 1 1 d . . . . .
C8 C 0.5493(3) 0.6970(6) 0.70837(17) 0.0619(10) Uani 1 1 d . . . . .
C9 C 0.6056(3) 0.5420(6) 0.68024(16) 0.0545(9) Uani 1 1 d . . . . .
C10 C 0.6341(3) 0.5931(6) 0.62589(17) 0.0632(10) Uani 1 1 d . . . . .
H10 H 0.614732 0.726428 0.606746 0.076 Uiso 1 1 calc R U . . .
C11 C 0.6910(3) 0.4481(6) 0.60011(17) 0.0576(10) Uani 1 1 d . . . . .
H11 H 0.709454 0.483646 0.563619 0.069 Uiso 1 1 calc R U . . .
C12 C 0.7206(2) 0.2498(5) 0.62824(15) 0.0498(9) Uani 1 1 d . . . . .
C13 C 0.6910(3) 0.1974(6) 0.68269(16) 0.0563(9) Uani 1 1 d . . . . .
H13 H 0.709790 0.063608 0.701702 0.068 Uiso 1 1 calc R U . . .
C14 C 0.6345(3) 0.3423(6) 0.70809(17) 0.0579(10) Uani 1 1 d . . . . .
H14 H 0.615331 0.306421 0.744361 0.069 Uiso 1 1 calc R U . . .
C15 C 0.7827(3) 0.0907(6) 0.60286(16) 0.0533(9) Uani 1 1 d . . . . .
C16 C 0.8024(3) 0.1270(6) 0.53891(16) 0.0529(9) Uani 1 1 d . . . . .
C17 C 0.7380(3) -0.0115(6) 0.48548(16) 0.0521(9) Uani 1 1 d . . . . .
C18 C 0.6860(3) 0.2859(7) 0.4167(2) 0.0810(13) Uani 1 1 d . . . . .
H18A H 0.677267 0.325275 0.374017 0.121 Uiso 1 1 calc R U . . .
H18B H 0.729620 0.391481 0.442650 0.121 Uiso 1 1 calc R U . . .
H18C H 0.618767 0.281722 0.426226 0.121 Uiso 1 1 calc R U . . .
C19 C 0.5673(3) -0.1705(7) 0.45559(19) 0.0766(12) Uani 1 1 d . . . . .
H19A H 0.504709 -0.185844 0.469964 0.115 Uiso 1 1 calc R U . . .
H19B H 0.597090 -0.311499 0.452615 0.115 Uiso 1 1 calc R U . . .
H19C H 0.550651 -0.102497 0.415547 0.115 Uiso 1 1 calc R U . . .
C20 C 0.8833(3) -0.2288(7) 0.4735(2) 0.0862(14) Uani 1 1 d . . . . .
H20A H 0.907265 -0.376816 0.476279 0.129 Uiso 1 1 calc R U . . .
H20B H 0.932252 -0.141129 0.502664 0.129 Uiso 1 1 calc R U . . .
H20C H 0.877810 -0.175187 0.432330 0.129 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 C17 1.381(4) . ?
O1 C18 1.449(4) . ?
O2 C15 1.214(4) . ?
O3 C16 1.209(4) . ?
O4 C17 1.379(4) . ?
O4 C19 1.441(4) . ?
O5 C17 1.404(4) . ?
O5 C20 1.426(4) . ?
C1 C2 1.381(5) . ?
C1 C6 1.383(5) . ?
C1 C7 1.439(5) . ?
C2 C3 1.370(5) . ?
C3 C4 1.368(6) . ?
C4 C5 1.362(6) . ?
C5 C6 1.383(6) . ?
C7 C8 1.195(5) . ?
C8 C9 1.442(5) . ?
C9 C14 1.386(5) . ?
C9 C10 1.389(5) . ?
C10 C11 1.377(5) . ?
C11 C12 1.382(5) . ?
C12 C13 1.400(5) . ?
C12 C15 1.473(5) . ?
C13 C14 1.369(5) . ?
C15 C16 1.526(5) . ?
C16 C17 1.537(5) . ?

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
C17 O1 C18 114.1(3) . . ?
C17 O4 C19 115.9(3) . . ?
C17 O5 C20 116.2(3) . . ?
C2 C1 C6 118.8(4) . . ?
C2 C1 C7 120.9(3) . . ?
C6 C1 C7 120.3(4) . . ?
C3 C2 C1 120.9(4) . . ?
C4 C3 C2 120.0(4) . . ?
C5 C4 C3 119.9(4) . . ?
C4 C5 C6 120.9(4) . . ?
C1 C6 C5 119.5(4) . . ?
C8 C7 C1 177.7(4) . . ?
C7 C8 C9 178.3(4) . . ?
C14 C9 C10 119.1(3) . . ?
C14 C9 C8 120.3(3) . . ?
C10 C9 C8 120.5(3) . . ?
C11 C10 C9 120.5(3) . . ?
C10 C11 C12 120.3(3) . . ?
C11 C12 C13 119.2(3) . . ?
C11 C12 C15 122.2(3) . . ?
C13 C12 C15 118.6(3) . . ?
C14 C13 C12 120.2(3) . . ?
C13 C14 C9 120.6(3) . . ?
O2 C15 C12 124.5(3) . . ?
O2 C15 C16 115.6(3) . . ?
C12 C15 C16 119.9(3) . . ?
O3 C16 C15 121.0(3) . . ?
O3 C16 C17 121.8(3) . . ?
C15 C16 C17 116.9(3) . . ?
O4 C17 O1 115.0(3) . . ?
O4 C17 O5 107.0(3) . . ?
O1 C17 O5 106.6(3) . . ?
O4 C17 C16 105.3(3) . . ?
O1 C17 C16 113.4(3) . . ?
O5 C17 C16 109.4(3) . . ?

_refine_diff_density_max         0.245
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.047



