# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_MGr0113_10A_K_0ma
_database_code_depnum_ccdc_archive 'CCDC 2090872'
loop_
_audit_author_name
_audit_author_address
'Marek Grzybowski'
;Institute of Organic Chemistry PAS
Poland
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2022-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H16 O2'
_chemical_formula_sum            'C21 H16 O2'
_chemical_formula_weight         300.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 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+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'x-1/2, y-1/2, -z-1/2'

_cell_length_a                   20.1860(15)
_cell_length_b                   7.3066(6)
_cell_length_c                   20.4874(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3021.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1162
_cell_measurement_theta_min      4.32
_cell_measurement_theta_max      60.39

_exptl_crystal_description       cube
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.131
_exptl_absorpt_coefficient_mu    0.664
_shelx_estimated_absorpt_T_min   0.895
_shelx_estimated_absorpt_T_max   0.918
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8950
_exptl_absorpt_correction_T_max  0.9180
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 Crystal selected for X-ray experiment was small cube
 with dimensions 0.171 mm x 0.170 mm x 0.131 mm
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43029
_diffrn_reflns_av_unetI/netI     0.1496
_diffrn_reflns_av_R_equivalents  0.2010
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.316
_diffrn_reflns_theta_max         60.387
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measured_fraction_theta_full 0.767
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_Laue_measured_fraction_full 0.767
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_point_group_measured_fraction_full 0.767
_reflns_number_total             2097
_reflns_number_gt                1162
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0951P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2097
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1656
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.1707
_refine_ls_wR_factor_gt          0.1489
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_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 1.08966(11) 0.1622(4) 0.97693(13) 0.0634(9) Uani 1 1 d . . . . .
H1 H 1.1265 0.1864 0.9625 0.095 Uiso 1 1 calc R U . . .
O2 O 0.71762(10) 0.3157(4) 1.05576(12) 0.0553(9) Uani 1 1 d . . . . .
C1 C 0.88649(16) 0.5416(5) 0.86133(19) 0.0366(10) Uani 1 1 d . . . . .
C2 C 0.94637(16) 0.4622(5) 0.88512(18) 0.0367(10) Uani 1 1 d . . . . .
C3 C 1.01064(19) 0.4597(6) 0.8592(2) 0.0460(11) Uani 1 1 d . . . . .
C4 C 1.0591(2) 0.3614(6) 0.8901(2) 0.0441(11) Uani 1 1 d . . . . .
C5 C 1.04520(16) 0.2630(5) 0.9474(2) 0.0402(11) Uani 1 1 d . . . . .
C6 C 0.98078(17) 0.2686(5) 0.9753(2) 0.0358(10) Uani 1 1 d . . . . .
C7 C 0.93315(16) 0.3675(5) 0.94500(18) 0.0337(10) Uani 1 1 d . . . . .
C8 C 0.86218(15) 0.3930(5) 0.95881(19) 0.0334(10) Uani 1 1 d . . . . .
C9 C 0.82434(18) 0.3380(5) 1.0087(2) 0.0388(11) Uani 1 1 d . . . . .
C10 C 0.75428(18) 0.3713(5) 1.0077(2) 0.0385(10) Uani 1 1 d . . . . .
C11 C 0.7278(2) 0.4625(5) 0.9530(2) 0.0405(12) Uani 1 1 d . . . . .
C12 C 0.76644(18) 0.5272(5) 0.9035(2) 0.0387(11) Uani 1 1 d . . . . .
C13 C 0.83536(17) 0.4942(5) 0.90535(18) 0.0342(10) Uani 1 1 d . . . . .
C14 C 0.87767(16) 0.6465(5) 0.80029(18) 0.0367(10) Uani 1 1 d . . . . .
C15 C 0.90596(17) 0.8225(6) 0.7967(2) 0.0445(11) Uani 1 1 d . . . . .
C16 C 0.89644(19) 0.9190(6) 0.7395(3) 0.0615(13) Uani 1 1 d . . . . .
H16 H 0.9149 1.0351 0.7356 0.074 Uiso 1 1 calc R U . . .
C17 C 0.8606(3) 0.8494(9) 0.6883(3) 0.0669(16) Uani 1 1 d . . . . .
C18 C 0.8335(2) 0.6763(9) 0.6936(2) 0.0550(13) Uani 1 1 d . . . . .
C19 C 0.84180(15) 0.5750(6) 0.7493(2) 0.0407(11) Uani 1 1 d . . . . .
C20 C 0.94332(19) 0.9080(5) 0.85200(19) 0.0637(13) Uani 1 1 d . . . . .
H20A H 0.9434 1.0386 0.8469 0.096 Uiso 1 1 calc R U . . .
H20B H 0.9881 0.8637 0.8520 0.096 Uiso 1 1 calc R U . . .
H20C H 0.9224 0.8766 0.8926 0.096 Uiso 1 1 calc R U . . .
C21 C 0.81251(18) 0.3850(6) 0.7522(2) 0.0635(13) Uani 1 1 d . . . . .
H21A H 0.7702 0.3898 0.7737 0.095 Uiso 1 1 calc R U . . .
H21B H 0.8417 0.3060 0.7762 0.095 Uiso 1 1 calc R U . . .
H21C H 0.8070 0.3386 0.7088 0.095 Uiso 1 1 calc R U . . .
H3 H 1.0192(16) 0.524(5) 0.818(2) 0.068(14) Uiso 1 1 d . . . . .
H11 H 0.6836(16) 0.479(4) 0.9482(14) 0.039(11) Uiso 1 1 d . . . . .
H12 H 0.7479(16) 0.591(4) 0.8636(16) 0.047(11) Uiso 1 1 d . . . . .
H4 H 1.1064(18) 0.356(5) 0.8740(16) 0.073(13) Uiso 1 1 d . . . . .
H6 H 0.9720(12) 0.205(4) 1.0158(14) 0.022(9) Uiso 1 1 d . . . . .
H18 H 0.8109(15) 0.634(5) 0.6564(18) 0.050(13) Uiso 1 1 d . . . . .
H9 H 0.8392(12) 0.282(4) 1.0428(13) 0.009(10) Uiso 1 1 d . . . . .
H17 H 0.8528(16) 0.922(6) 0.6545(19) 0.061(15) Uiso 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
O1 C5 1.309(4) . ?
O1 H1 0.8200 . ?
O2 C10 1.297(4) . ?
C1 C13 1.414(4) . ?
C1 C2 1.427(4) . ?
C1 C14 1.477(5) . ?
C2 C3 1.402(5) . ?
C2 C7 1.434(5) . ?
C3 C4 1.369(5) . ?
C3 H3 0.97(4) . ?
C4 C5 1.405(5) . ?
C4 H4 1.01(3) . ?
C5 C6 1.421(5) . ?
C6 C7 1.353(4) . ?
C6 H6 0.97(3) . ?
C7 C8 1.472(5) . ?
C8 C9 1.338(5) . ?
C8 C13 1.428(4) . ?
C9 C10 1.435(5) . ?
C9 H9 0.86(3) . ?
C10 C11 1.409(4) . ?
C11 C12 1.363(5) . ?
C11 H11 0.91(3) . ?
C12 C13 1.412(5) . ?
C12 H12 1.01(3) . ?
C14 C19 1.375(5) . ?
C14 C15 1.409(5) . ?
C15 C16 1.381(5) . ?
C15 C20 1.497(5) . ?
C16 C17 1.373(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(6) . ?
C17 H17 0.89(4) . ?
C18 C19 1.370(5) . ?
C18 H18 0.94(4) . ?
C19 C21 1.510(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C5 O1 H1 109.5 . . ?
C13 C1 C2 107.5(3) . . ?
C13 C1 C14 125.4(3) . . ?
C2 C1 C14 127.0(3) . . ?
C3 C2 C1 131.3(4) . . ?
C3 C2 C7 119.4(3) . . ?
C1 C2 C7 109.3(3) . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3 121(2) . . ?
C2 C3 H3 119(2) . . ?
C3 C4 C5 120.8(4) . . ?
C3 C4 H4 123(2) . . ?
C5 C4 H4 116.1(19) . . ?
O1 C5 C4 122.5(3) . . ?
O1 C5 C6 117.3(4) . . ?
C4 C5 C6 120.2(4) . . ?
C7 C6 C5 118.8(4) . . ?
C7 C6 H6 121.3(15) . . ?
C5 C6 H6 119.9(15) . . ?
C6 C7 C2 121.2(3) . . ?
C6 C7 C8 132.1(4) . . ?
C2 C7 C8 106.5(3) . . ?
C9 C8 C13 121.7(3) . . ?
C9 C8 C7 131.6(4) . . ?
C13 C8 C7 106.7(3) . . ?
C8 C9 C10 120.0(4) . . ?
C8 C9 H9 124.2(17) . . ?
C10 C9 H9 115.8(17) . . ?
O2 C10 C11 122.4(3) . . ?
O2 C10 C9 119.9(4) . . ?
C11 C10 C9 117.7(4) . . ?
C12 C11 C10 122.6(4) . . ?
C12 C11 H11 115.8(19) . . ?
C10 C11 H11 121.6(19) . . ?
C11 C12 C13 119.0(4) . . ?
C11 C12 H12 123.2(18) . . ?
C13 C12 H12 117.7(18) . . ?
C12 C13 C1 131.3(4) . . ?
C12 C13 C8 118.8(3) . . ?
C1 C13 C8 109.8(3) . . ?
C19 C14 C15 121.4(4) . . ?
C19 C14 C1 120.7(4) . . ?
C15 C14 C1 117.9(4) . . ?
C16 C15 C14 117.0(4) . . ?
C16 C15 C20 119.9(4) . . ?
C14 C15 C20 123.1(4) . . ?
C17 C16 C15 122.2(5) . . ?
C17 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
C16 C17 C18 119.2(5) . . ?
C16 C17 H17 118(3) . . ?
C18 C17 H17 123(3) . . ?
C19 C18 C17 120.7(5) . . ?
C19 C18 H18 124(2) . . ?
C17 C18 H18 115(2) . . ?
C18 C19 C14 119.5(4) . . ?
C18 C19 C21 118.8(4) . . ?
C14 C19 C21 121.7(4) . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C13 C1 C2 C3 176.9(4) . . . . ?
C14 C1 C2 C3 -0.2(6) . . . . ?
C13 C1 C2 C7 -1.1(4) . . . . ?
C14 C1 C2 C7 -178.2(3) . . . . ?
C1 C2 C3 C4 -175.4(4) . . . . ?
C7 C2 C3 C4 2.4(5) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 C4 C5 O1 177.4(3) . . . . ?
C3 C4 C5 C6 -1.8(5) . . . . ?
O1 C5 C6 C7 -178.2(3) . . . . ?
C4 C5 C6 C7 1.1(5) . . . . ?
C5 C6 C7 C2 1.4(5) . . . . ?
C5 C6 C7 C8 176.3(3) . . . . ?
C3 C2 C7 C6 -3.2(5) . . . . ?
C1 C2 C7 C6 175.1(3) . . . . ?
C3 C2 C7 C8 -179.2(3) . . . . ?
C1 C2 C7 C8 -0.9(4) . . . . ?
C6 C7 C8 C9 6.4(6) . . . . ?
C2 C7 C8 C9 -178.2(4) . . . . ?
C6 C7 C8 C13 -172.8(3) . . . . ?
C2 C7 C8 C13 2.6(3) . . . . ?
C13 C8 C9 C10 3.5(5) . . . . ?
C7 C8 C9 C10 -175.6(3) . . . . ?
C8 C9 C10 O2 179.1(3) . . . . ?
C8 C9 C10 C11 0.0(5) . . . . ?
O2 C10 C11 C12 177.5(3) . . . . ?
C9 C10 C11 C12 -3.5(5) . . . . ?
C10 C11 C12 C13 3.2(5) . . . . ?
C11 C12 C13 C1 179.0(3) . . . . ?
C11 C12 C13 C8 0.4(5) . . . . ?
C2 C1 C13 C12 -175.9(3) . . . . ?
C14 C1 C13 C12 1.3(6) . . . . ?
C2 C1 C13 C8 2.9(4) . . . . ?
C14 C1 C13 C8 -180.0(3) . . . . ?
C9 C8 C13 C12 -3.8(5) . . . . ?
C7 C8 C13 C12 175.5(3) . . . . ?
C9 C8 C13 C1 177.3(3) . . . . ?
C7 C8 C13 C1 -3.4(4) . . . . ?
C13 C1 C14 C19 -65.8(5) . . . . ?
C2 C1 C14 C19 110.8(4) . . . . ?
C13 C1 C14 C15 113.0(4) . . . . ?
C2 C1 C14 C15 -70.4(5) . . . . ?
C19 C14 C15 C16 -0.5(5) . . . . ?
C1 C14 C15 C16 -179.2(3) . . . . ?
C19 C14 C15 C20 177.8(3) . . . . ?
C1 C14 C15 C20 -0.9(5) . . . . ?
C14 C15 C16 C17 0.7(5) . . . . ?
C20 C15 C16 C17 -177.7(3) . . . . ?
C15 C16 C17 C18 -0.6(6) . . . . ?
C16 C17 C18 C19 0.4(6) . . . . ?
C17 C18 C19 C14 -0.3(5) . . . . ?
C17 C18 C19 C21 -178.8(3) . . . . ?
C15 C14 C19 C18 0.3(5) . . . . ?
C1 C14 C19 C18 179.0(3) . . . . ?
C15 C14 C19 C21 178.8(3) . . . . ?
C1 C14 C19 C21 -2.5(5) . . . . ?

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
C11 H11 O1 0.91(3) 2.65(3) 3.267(5) 126(2) 2_457
O1 H1 O2 0.82 1.88 2.673(3) 163.5 2_557
C11 H11 O1 0.91(3) 2.65(3) 3.267(5) 126(2) 2_457
O1 H1 O2 0.82 1.88 2.673(3) 163.5 2_557
C11 H11 O1 0.91(3) 2.65(3) 3.267(5) 126(2) 2_457
O1 H1 O2 0.82 1.88 2.673(3) 163.5 2_557
O1 H1 O2 0.82 1.88 2.673(3) 163.5 2_557
C11 H11 O1 0.91(3) 2.65(3) 3.267(5) 126(2) 2_457
O1 H1 O2 0.82 1.88 2.673(3) 163.5 2_557
C11 H11 O1 0.91(3) 2.65(3) 3.267(5) 126(2) 2_457
O1 H1 O2 0.82 1.88 2.673(3) 163.5 2_557
C11 H11 O1 0.91(3) 2.65(3) 3.267(5) 126(2) 2_457

_refine_diff_density_max         0.265
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.060

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform, ethanol, n-pentane'
