# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_mo220420c
_database_code_depnum_ccdc_archive 'CCDC 2208411'
_audit_update_record             
;
2022-09-20 deposited with the CCDC.	2023-03-14 downloaded from the CCDC.
;
_audit_creation_date             2022-04-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6427)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 O2'
_chemical_formula_sum            'C21 H14 O2'
_chemical_formula_weight         298.32
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   13.785(5)
_cell_length_b                   8.252(3)
_cell_length_c                   12.807(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.271(7)
_cell_angle_gamma                90
_cell_volume                     1448.2(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1318
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      20.907
_cell_measurement_theta_min      2.881
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0944 before and 0.0682 after correction.
The Ratio of minimum to maximum transmission is 0.6828.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1020
_diffrn_reflns_av_unetI/netI     0.1017
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14650
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.166
_diffrn_reflns_theta_min         1.486
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1709
_reflns_number_total             3883
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3883
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1519
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      0.947
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0530P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1493
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20)
;
_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 0.19497(9) 0.18464(17) 0.57235(11) 0.0439(4) Uani 1 1 d . . . . .
O2 O 0.12119(12) 0.0833(2) 0.37671(13) 0.0647(5) Uani 1 1 d . . . . .
C1 C 0.19316(14) 0.2979(3) 0.48596(16) 0.0399(5) Uani 1 1 d . . . . .
C2 C 0.13244(15) 0.2291(3) 0.38933(18) 0.0441(6) Uani 1 1 d . . . . .
C3 C 0.09403(16) 0.3457(3) 0.31059(18) 0.0495(6) Uani 1 1 d . . . . .
H3 H 0.0762 0.3119 0.2419 0.059 Uiso 1 1 calc R U . . .
C4 C 0.08410(16) 0.5009(3) 0.33615(18) 0.0507(6) Uani 1 1 d . . . . .
H4 H 0.0581 0.5724 0.2843 0.061 Uiso 1 1 calc R U . . .
C5 C 0.11192(14) 0.5638(3) 0.44122(17) 0.0421(5) Uani 1 1 d . . . . .
C6 C 0.09148(16) 0.7234(3) 0.4676(2) 0.0521(6) Uani 1 1 d . . . . .
H6 H 0.0615 0.7927 0.4166 0.063 Uiso 1 1 calc R U . . .
C7 C 0.11541(17) 0.7794(3) 0.5685(2) 0.0564(7) Uani 1 1 d . . . . .
H7 H 0.1026 0.8864 0.5850 0.068 Uiso 1 1 calc R U . . .
C8 C 0.15811(17) 0.6771(3) 0.6449(2) 0.0576(6) Uani 1 1 d . . . . .
H8 H 0.1727 0.7143 0.7133 0.069 Uiso 1 1 calc R U . . .
C9 C 0.17943(16) 0.5186(3) 0.61985(18) 0.0483(6) Uani 1 1 d . . . . .
H9 H 0.2081 0.4498 0.6719 0.058 Uiso 1 1 calc R U . . .
C10 C 0.15863(14) 0.4617(3) 0.51841(17) 0.0392(5) Uani 1 1 d . . . . .
C11 C 0.30108(14) 0.3097(3) 0.45709(16) 0.0443(6) Uani 1 1 d . . . . .
H11A H 0.3078 0.2589 0.3900 0.053 Uiso 1 1 calc R U . . .
H11B H 0.3228 0.4214 0.4553 0.053 Uiso 1 1 calc R U . . .
C12 C 0.35582(14) 0.2182(2) 0.54601(16) 0.0382(5) Uani 1 1 d . . . . .
C13 C 0.45702(15) 0.1917(3) 0.56908(17) 0.0418(5) Uani 1 1 d . . . . .
C14 C 0.52744(16) 0.2552(3) 0.50817(19) 0.0511(6) Uani 1 1 d . . . . .
H14 H 0.5081 0.3213 0.4509 0.061 Uiso 1 1 calc R U . . .
C15 C 0.62401(17) 0.2199(3) 0.5331(2) 0.0610(7) Uani 1 1 d . . . . .
H15 H 0.6699 0.2617 0.4923 0.073 Uiso 1 1 calc R U . . .
C16 C 0.65470(19) 0.1213(3) 0.6196(2) 0.0664(8) Uani 1 1 d . . . . .
H16 H 0.7207 0.0983 0.6358 0.080 Uiso 1 1 calc R U . . .
C17 C 0.58853(18) 0.0594(3) 0.6796(2) 0.0607(7) Uani 1 1 d . . . . .
H17 H 0.6099 -0.0049 0.7372 0.073 Uiso 1 1 calc R U . . .
C18 C 0.48795(16) 0.0907(3) 0.65634(18) 0.0476(6) Uani 1 1 d . . . . .
C19 C 0.41698(17) 0.0216(3) 0.71526(18) 0.0508(6) Uani 1 1 d . . . . .
H19 H 0.4376 -0.0445 0.7722 0.061 Uiso 1 1 calc R U . . .
C20 C 0.31968(16) 0.0487(3) 0.69130(17) 0.0451(6) Uani 1 1 d . . . . .
H20 H 0.2739 0.0027 0.7306 0.054 Uiso 1 1 calc R U . . .
C21 C 0.29128(14) 0.1491(2) 0.60491(16) 0.0375(5) 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
O1 C1 1.446(2) . ?
O1 C21 1.379(2) . ?
O2 C2 1.221(3) . ?
C1 C2 1.526(3) . ?
C1 C10 1.507(3) . ?
C1 C11 1.575(3) . ?
C2 C3 1.452(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.333(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.454(3) . ?
C5 C6 1.396(3) . ?
C5 C10 1.401(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.379(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.374(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.385(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.500(3) . ?
C12 C13 1.411(3) . ?
C12 C21 1.354(3) . ?
C13 C14 1.411(3) . ?
C13 C18 1.422(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.366(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.402(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.355(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.410(3) . ?
C18 C19 1.419(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.361(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.403(3) . ?

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
C21 O1 C1 107.72(15) . . ?
O1 C1 C2 110.00(17) . . ?
O1 C1 C10 110.39(17) . . ?
O1 C1 C11 106.37(15) . . ?
C2 C1 C11 106.34(16) . . ?
C10 C1 C2 113.31(17) . . ?
C10 C1 C11 110.13(17) . . ?
O2 C2 C1 121.6(2) . . ?
O2 C2 C3 122.0(2) . . ?
C3 C2 C1 116.3(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 118.4 . . ?
C3 C4 C5 123.1(2) . . ?
C5 C4 H4 118.4 . . ?
C6 C5 C4 121.4(2) . . ?
C6 C5 C10 119.1(2) . . ?
C10 C5 C4 119.5(2) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.6(2) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.1(2) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.0(2) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.7(2) . . ?
C10 C9 H9 119.6 . . ?
C5 C10 C1 118.7(2) . . ?
C9 C10 C1 121.67(19) . . ?
C9 C10 C5 119.4(2) . . ?
C1 C11 H11A 111.5 . . ?
C1 C11 H11B 111.5 . . ?
H11A C11 H11B 109.3 . . ?
C12 C11 C1 101.56(16) . . ?
C12 C11 H11A 111.5 . . ?
C12 C11 H11B 111.5 . . ?
C13 C12 C11 129.86(19) . . ?
C21 C12 C11 109.18(17) . . ?
C21 C12 C13 120.87(19) . . ?
C12 C13 C18 117.4(2) . . ?
C14 C13 C12 123.4(2) . . ?
C14 C13 C18 119.1(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.7(3) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.3(3) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C13 118.5(2) . . ?
C17 C18 C19 122.3(2) . . ?
C19 C18 C13 119.3(2) . . ?
C18 C19 H19 118.9 . . ?
C20 C19 C18 122.2(2) . . ?
C20 C19 H19 118.9 . . ?
C19 C20 H20 121.4 . . ?
C19 C20 C21 117.3(2) . . ?
C21 C20 H20 121.4 . . ?
O1 C21 C20 122.71(19) . . ?
C12 C21 O1 114.31(18) . . ?
C12 C21 C20 122.98(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 O2 -25.3(3) . . . . ?
O1 C1 C2 C3 158.32(17) . . . . ?
O1 C1 C10 C5 -152.48(17) . . . . ?
O1 C1 C10 C9 33.3(3) . . . . ?
O1 C1 C11 C12 -9.2(2) . . . . ?
O2 C2 C3 C4 162.1(2) . . . . ?
C1 O1 C21 C12 -3.8(2) . . . . ?
C1 O1 C21 C20 176.66(19) . . . . ?
C1 C2 C3 C4 -21.6(3) . . . . ?
C1 C11 C12 C13 -176.4(2) . . . . ?
C1 C11 C12 C21 7.2(2) . . . . ?
C2 C1 C10 C5 -28.6(3) . . . . ?
C2 C1 C10 C9 157.17(19) . . . . ?
C2 C1 C11 C12 -126.41(18) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C3 C4 C5 C6 -173.5(2) . . . . ?
C3 C4 C5 C10 5.3(3) . . . . ?
C4 C5 C6 C7 177.8(2) . . . . ?
C4 C5 C10 C1 9.7(3) . . . . ?
C4 C5 C10 C9 -175.92(19) . . . . ?
C5 C6 C7 C8 -1.2(3) . . . . ?
C6 C5 C10 C1 -171.43(18) . . . . ?
C6 C5 C10 C9 2.9(3) . . . . ?
C6 C7 C8 C9 1.6(4) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C8 C9 C10 C1 171.6(2) . . . . ?
C8 C9 C10 C5 -2.6(3) . . . . ?
C10 C1 C2 O2 -149.4(2) . . . . ?
C10 C1 C2 C3 34.2(3) . . . . ?
C10 C1 C11 C12 110.45(19) . . . . ?
C10 C5 C6 C7 -1.1(3) . . . . ?
C11 C1 C2 O2 89.4(2) . . . . ?
C11 C1 C2 C3 -86.9(2) . . . . ?
C11 C1 C10 C5 90.4(2) . . . . ?
C11 C1 C10 C9 -83.9(2) . . . . ?
C11 C12 C13 C14 1.4(3) . . . . ?
C11 C12 C13 C18 -176.3(2) . . . . ?
C11 C12 C21 O1 -2.6(2) . . . . ?
C11 C12 C21 C20 176.9(2) . . . . ?
C12 C13 C14 C15 -177.7(2) . . . . ?
C12 C13 C18 C17 178.61(19) . . . . ?
C12 C13 C18 C19 0.2(3) . . . . ?
C13 C12 C21 O1 -179.38(18) . . . . ?
C13 C12 C21 C20 0.1(3) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
C13 C18 C19 C20 -0.1(3) . . . . ?
C14 C13 C18 C17 0.8(3) . . . . ?
C14 C13 C18 C19 -177.57(19) . . . . ?
C14 C15 C16 C17 0.1(4) . . . . ?
C15 C16 C17 C18 0.7(4) . . . . ?
C16 C17 C18 C13 -1.1(3) . . . . ?
C16 C17 C18 C19 177.2(2) . . . . ?
C17 C18 C19 C20 -178.4(2) . . . . ?
C18 C13 C14 C15 -0.1(3) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
C19 C20 C21 O1 179.47(19) . . . . ?
C19 C20 C21 C12 0.0(3) . . . . ?
C21 O1 C1 C2 122.94(17) . . . . ?
C21 O1 C1 C10 -111.29(18) . . . . ?
C21 O1 C1 C11 8.2(2) . . . . ?
C21 C12 C13 C14 177.4(2) . . . . ?
C21 C12 C13 C18 -0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
