# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_211122a_a
_database_code_depnum_ccdc_archive 'CCDC 2132853'
loop_
_audit_author_name
_audit_author_address
'Xiang Zuo'
;Tongji University
China
;
_audit_update_record             
;
2022-01-06 deposited with the CCDC.	2022-08-03 downloaded from the CCDC.
;
_audit_creation_date             2021-11-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C20 H14 O)'
_chemical_formula_sum            'C40 H28 O2'
_chemical_formula_weight         540.62
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.290(12)
_cell_length_b                   7.541(5)
_cell_length_c                   22.082(15)
_cell_angle_alpha                90
_cell_angle_beta                 98.62(2)
_cell_angle_gamma                90
_cell_volume                     2847(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5105
_cell_measurement_temperature    280.0
_cell_measurement_theta_max      25.43
_cell_measurement_theta_min      2.95
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0974 before and 0.0761 after correction.
The Ratio of minimum to maximum transmission is 0.7986.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15738
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.660
_diffrn_reflns_theta_min         2.798
_diffrn_ambient_temperature      280.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_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             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2002
_reflns_number_total             2682
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0110(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2682
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0506
_refine_ls_restrained_S_all      1.081
_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)+(0.0431P)²+1.8420P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1301
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(H14A)=Sof(H14B)=Sof(O1B)=1-FVAR(1)
 Sof(H13A)=Sof(H13B)=Sof(O1A)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C16(H16),
 C17(H17), C18(H18), C19(H19)
;
_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
C1 C 0.27582(12) 0.5400(2) 0.59099(8) 0.0502(5) Uani 1 1 d . . . . .
C2 C 0.19913(13) 0.4798(3) 0.57634(10) 0.0645(6) Uani 1 1 d . . . . .
H2 H 0.168359 0.468238 0.607233 0.077 Uiso 1 1 calc R U . . .
C3 C 0.16802(15) 0.4372(3) 0.51728(13) 0.0778(7) Uani 1 1 d . . . . .
H3 H 0.116876 0.395989 0.508449 0.093 Uiso 1 1 calc R U . . .
C4 C 0.21305(17) 0.4558(3) 0.47103(11) 0.0803(8) Uani 1 1 d . . . . .
H4 H 0.192177 0.427386 0.430916 0.096 Uiso 1 1 calc R U . . .
C5 C 0.28948(15) 0.5171(3) 0.48437(10) 0.0674(6) Uani 1 1 d . . . . .
H5 H 0.319455 0.529681 0.453002 0.081 Uiso 1 1 calc R U . . .
C6 C 0.32173(12) 0.5598(3) 0.54425(9) 0.0538(5) Uani 1 1 d . . . . .
C7 C 0.30648(11) 0.5881(2) 0.65590(9) 0.0496(5) Uani 1 1 d . . . . .
C8 C 0.26958(12) 0.7237(3) 0.68430(9) 0.0581(5) Uani 1 1 d . . . . .
H8 H 0.228750 0.786130 0.661635 0.070 Uiso 1 1 calc R U . . .
C9 C 0.29248(13) 0.7667(3) 0.74526(10) 0.0645(6) Uani 1 1 d . . . . .
H9 H 0.267556 0.857925 0.763090 0.077 Uiso 1 1 calc R U . . .
C10 C 0.35253(13) 0.6735(3) 0.77954(10) 0.0659(6) Uani 1 1 d . . . . .
H10 H 0.367796 0.700723 0.820678 0.079 Uiso 1 1 calc R U . . .
C11 C 0.38988(12) 0.5394(3) 0.75227(10) 0.0611(6) Uani 1 1 d . . . . .
H11 H 0.430293 0.477177 0.775568 0.073 Uiso 1 1 calc R U . . .
C12 C 0.36821(10) 0.4951(3) 0.69045(8) 0.0494(5) Uani 1 1 d . . . . .
C13 C 0.40238(14) 0.6388(3) 0.55741(10) 0.0698(6) Uani 1 1 d . . . . .
H13A H 0.415877 0.681261 0.518875 0.084 Uiso 0.794(5) 1 calc R U P A 1
H13B H 0.399242 0.741932 0.583171 0.084 Uiso 0.794(5) 1 calc R U P A 1
C14 C 0.46800(13) 0.5294(3) 0.58667(11) 0.0667(6) Uani 1 1 d . . . . .
H14A H 0.499738 0.604973 0.616087 0.080 Uiso 0.206(5) 1 calc R U P A 2
H14B H 0.499577 0.501499 0.555144 0.080 Uiso 0.206(5) 1 calc R U P A 2
C15 C 0.45626(11) 0.3574(3) 0.61938(9) 0.0520(5) Uani 1 1 d . . . . .
C16 C 0.49824(11) 0.2100(3) 0.60406(10) 0.0575(5) Uani 1 1 d . . . . .
H16 H 0.531242 0.221949 0.574701 0.069 Uiso 1 1 calc R U . . .
C17 C 0.49195(12) 0.0466(3) 0.63149(10) 0.0595(5) Uani 1 1 d . . . . .
H17 H 0.519187 -0.050693 0.619663 0.071 Uiso 1 1 calc R U . . .
C18 C 0.44515(12) 0.0290(3) 0.67635(10) 0.0588(5) Uani 1 1 d . . . . .
H18 H 0.440452 -0.080352 0.694945 0.071 Uiso 1 1 calc R U . . .
C19 C 0.40508(11) 0.1752(3) 0.69367(9) 0.0556(5) Uani 1 1 d . . . . .
H19 H 0.374709 0.162708 0.724785 0.067 Uiso 1 1 calc R U . . .
C20 C 0.40887(10) 0.3410(3) 0.66579(8) 0.0488(5) Uani 1 1 d . . . . .
O1A O 0.53381(11) 0.5704(3) 0.57628(11) 0.0839(9) Uani 0.794(5) 1 d . . P A 1
O1B O 0.4414(6) 0.6808(15) 0.5144(4) 0.117(5) Uani 0.206(5) 1 d . . P A 2


_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 1.393(3) . ?
C1 C6 1.401(3) . ?
C1 C7 1.497(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.372(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.394(3) . ?
C6 C13 1.504(3) . ?
C7 C8 1.402(3) . ?
C7 C12 1.403(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.384(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.401(3) . ?
C12 C20 1.503(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.471(3) . ?
C13 O1B 1.285(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.513(3) . ?
C14 O1A 1.233(3) . ?
C15 C16 1.396(3) . ?
C15 C20 1.410(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.376(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.386(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.399(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
C2 C1 C6 119.23(19) . . ?
C2 C1 C7 119.31(18) . . ?
C6 C1 C7 121.42(18) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.4(2) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.7(2) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.7(2) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C13 120.73(18) . . ?
C5 C6 C1 119.0(2) . . ?
C5 C6 C13 120.2(2) . . ?
C8 C7 C1 119.06(18) . . ?
C8 C7 C12 118.76(18) . . ?
C12 C7 C1 122.07(17) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.5(2) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.72(19) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(2) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.6(2) . . ?
C12 C11 H11 119.2 . . ?
C7 C12 C20 123.28(17) . . ?
C11 C12 C7 118.79(18) . . ?
C11 C12 C20 117.78(18) . . ?
C6 C13 H13A 107.4 . . ?
C6 C13 H13B 107.4 . . ?
H13A C13 H13B 106.9 . . ?
C14 C13 C6 119.6(2) . . ?
C14 C13 H13A 107.4 . . ?
C14 C13 H13B 107.4 . . ?
O1B C13 C6 121.9(6) . . ?
O1B C13 C14 90.4(5) . . ?
C13 C14 H14A 106.7 . . ?
C13 C14 H14B 106.7 . . ?
C13 C14 C15 122.70(18) . . ?
H14A C14 H14B 106.6 . . ?
C15 C14 H14A 106.7 . . ?
C15 C14 H14B 106.7 . . ?
O1A C14 C13 116.8(2) . . ?
O1A C14 C15 119.8(2) . . ?
C16 C15 C14 117.05(18) . . ?
C16 C15 C20 119.08(18) . . ?
C20 C15 C14 123.80(17) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.64(19) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.60(19) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.6(2) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.0 . . ?
C18 C19 C20 122.06(19) . . ?
C20 C19 H19 119.0 . . ?
C15 C20 C12 123.36(17) . . ?
C19 C20 C12 118.45(17) . . ?
C19 C20 C15 117.96(17) . . ?

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
C1 C2 C3 C4 -0.7(3) . . . . ?
C1 C6 C13 C14 78.3(3) . . . . ?
C1 C6 C13 O1B -170.3(6) . . . . ?
C1 C7 C8 C9 176.16(19) . . . . ?
C1 C7 C12 C11 -175.31(18) . . . . ?
C1 C7 C12 C20 0.1(3) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C2 C1 C6 C13 174.83(19) . . . . ?
C2 C1 C7 C8 -60.3(3) . . . . ?
C2 C1 C7 C12 116.0(2) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C5 C6 C13 -175.4(2) . . . . ?
C5 C6 C13 C14 -106.3(2) . . . . ?
C5 C6 C13 O1B 5.1(7) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C6 C1 C7 C8 117.5(2) . . . . ?
C6 C1 C7 C12 -66.2(3) . . . . ?
C6 C13 C14 C15 -16.5(3) . . . . ?
C6 C13 C14 O1A 153.6(2) . . . . ?
C7 C1 C2 C3 178.80(19) . . . . ?
C7 C1 C6 C5 -178.39(18) . . . . ?
C7 C1 C6 C13 -3.0(3) . . . . ?
C7 C8 C9 C10 -0.7(3) . . . . ?
C7 C12 C20 C15 67.9(3) . . . . ?
C7 C12 C20 C19 -117.7(2) . . . . ?
C8 C7 C12 C11 1.0(3) . . . . ?
C8 C7 C12 C20 176.44(18) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 C7 -0.8(3) . . . . ?
C10 C11 C12 C20 -176.6(2) . . . . ?
C11 C12 C20 C15 -116.6(2) . . . . ?
C11 C12 C20 C19 57.8(2) . . . . ?
C12 C7 C8 C9 -0.2(3) . . . . ?
C13 C14 C15 C16 130.7(2) . . . . ?
C13 C14 C15 C20 -52.5(3) . . . . ?
C14 C15 C16 C17 179.7(2) . . . . ?
C14 C15 C20 C12 -3.6(3) . . . . ?
C14 C15 C20 C19 -178.00(19) . . . . ?
C15 C16 C17 C18 -2.0(3) . . . . ?
C16 C15 C20 C12 173.24(18) . . . . ?
C16 C15 C20 C19 -1.2(3) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 C19 C20 1.7(3) . . . . ?
C18 C19 C20 C12 -175.70(18) . . . . ?
C18 C19 C20 C15 -1.0(3) . . . . ?
C20 C15 C16 C17 2.7(3) . . . . ?
O1A C14 C15 C16 -39.2(3) . . . . ?
O1A C14 C15 C20 137.7(2) . . . . ?
O1B C13 C14 C15 -144.3(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
