# Electronic Supplementary Material (ESI) 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_Rform_a_sq
_database_code_depnum_ccdc_archive 'CCDC 2286253'
loop_
_audit_author_name
_audit_author_address
'Huiyeong Ju'
;Korea Basic Science Institute (KBSI) Western Seoul Center
South Korea
;
_audit_update_record             
;
2023-08-02 deposited with the CCDC.	2023-12-05 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         'C24 H24 N2 O2'
_chemical_formula_sum            'C24 H24 N2 O2'
_chemical_formula_weight         372.45

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'
N N 0.0061 0.0033 '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                   5.8511(3)
_cell_length_b                   18.1921(10)
_cell_length_c                   21.3063(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2267.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    9973
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      28.00

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.091
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.128
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6930
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50659
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.239
_diffrn_reflns_theta_max         28.336
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5640
_reflns_number_gt                4522
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_max     0.997
_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. 
  
 Structure factors included contributions from the .fab file. 
  
 _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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0391P)²+0.2945P] 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 1667 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.1(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5640
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0870
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 -0.0434(2) 0.47804(8) 0.35565(7) 0.0517(4) Uani 1 1 d . . . . .
O2 O 0.3930(3) 0.23760(7) 0.31174(8) 0.0555(4) Uani 1 1 d . . . . .
N1 N 0.3824(3) 0.61482(8) 0.34964(9) 0.0463(4) Uani 1 1 d . . . . .
N2 N 0.8806(3) 0.23400(10) 0.40875(10) 0.0548(5) Uani 1 1 d . . . . .
C1 C 0.4041(4) 0.68566(11) 0.33414(12) 0.0542(6) Uani 1 1 d . . . . .
H1 H 0.546671 0.708234 0.340582 0.065 Uiso 1 1 calc R U . . .
C2 C 0.2300(4) 0.72766(12) 0.30927(12) 0.0576(6) Uani 1 1 d . . . . .
H2 H 0.253966 0.777379 0.299226 0.069 Uiso 1 1 calc R U . . .
C3 C 0.0216(4) 0.69542(12) 0.29952(12) 0.0610(6) Uani 1 1 d . . . . .
H3 H -0.099297 0.722222 0.281596 0.073 Uiso 1 1 calc R U . . .
C4 C -0.0078(4) 0.62260(11) 0.31656(11) 0.0504(5) Uani 1 1 d . . . . .
H4 H -0.150075 0.599369 0.311470 0.061 Uiso 1 1 calc R U . . .
C5 C 0.1766(3) 0.58465(9) 0.34126(9) 0.0368(4) Uani 1 1 d . . . . .
C6 C 0.1454(3) 0.50528(9) 0.35951(8) 0.0363(4) Uani 1 1 d . . . . .
C7 C 0.3468(3) 0.46065(9) 0.38360(9) 0.0355(4) Uani 1 1 d . . . . .
H7 H 0.488741 0.487521 0.373013 0.043 Uiso 1 1 calc R U . . .
C8 C 0.3328(4) 0.45396(11) 0.45625(9) 0.0446(5) Uani 1 1 d . . . . .
H8 H 0.466495 0.424504 0.469633 0.053 Uiso 1 1 calc R U . . .
C9 C 0.3562(6) 0.52900(13) 0.48755(11) 0.0710(8) Uani 1 1 d . . . . .
H9A H 0.491611 0.553550 0.471715 0.107 Uiso 1 1 calc R U . . .
H9B H 0.369552 0.522653 0.532605 0.107 Uiso 1 1 calc R U . . .
H9C H 0.222374 0.558506 0.478232 0.107 Uiso 1 1 calc R U . . .
C10 C 0.1210(5) 0.41395(16) 0.48014(12) 0.0696(7) Uani 1 1 d . . . . .
H10A H -0.014506 0.441540 0.468648 0.104 Uiso 1 1 calc R U . . .
H10B H 0.128949 0.409502 0.525453 0.104 Uiso 1 1 calc R U . . .
H10C H 0.113951 0.365353 0.461507 0.104 Uiso 1 1 calc R U . . .
C11 C 0.3510(3) 0.38583(9) 0.34850(9) 0.0365(4) Uani 1 1 d . . . . .
H11 H 0.203735 0.360699 0.356436 0.044 Uiso 1 1 calc R U . . .
C12 C 0.3724(3) 0.39829(9) 0.27803(9) 0.0364(4) Uani 1 1 d . . . . .
C13 C 0.5649(4) 0.43135(11) 0.25238(10) 0.0487(5) Uani 1 1 d . . . . .
H13 H 0.682450 0.447795 0.278967 0.058 Uiso 1 1 calc R U . . .
C14 C 0.5857(4) 0.44035(13) 0.18816(11) 0.0592(6) Uani 1 1 d . . . . .
H14 H 0.718014 0.462357 0.171637 0.071 Uiso 1 1 calc R U . . .
C15 C 0.4152(4) 0.41751(13) 0.14813(11) 0.0604(6) Uani 1 1 d . . . . .
H15 H 0.430848 0.423277 0.104494 0.072 Uiso 1 1 calc R U . . .
C16 C 0.2218(4) 0.38618(13) 0.17299(11) 0.0582(6) Uani 1 1 d . . . . .
H16 H 0.103201 0.370942 0.146219 0.070 Uiso 1 1 calc R U . . .
C17 C 0.2003(4) 0.37687(11) 0.23731(10) 0.0470(5) Uani 1 1 d . . . . .
H17 H 0.066345 0.355623 0.253588 0.056 Uiso 1 1 calc R U . . .
C18 C 0.5430(4) 0.33646(10) 0.37332(10) 0.0421(4) Uani 1 1 d . . . . .
H18A H 0.690319 0.359352 0.363445 0.051 Uiso 1 1 calc R U . . .
H18B H 0.530521 0.333454 0.419117 0.051 Uiso 1 1 calc R U . . .
C19 C 0.5406(4) 0.25975(10) 0.34678(10) 0.0408(4) Uani 1 1 d . . . . .
C20 C 0.7318(4) 0.20881(10) 0.36603(10) 0.0469(5) Uani 1 1 d . . . . .
C21 C 1.0525(4) 0.18909(14) 0.42506(13) 0.0655(7) Uani 1 1 d . . . . .
H21 H 1.158069 0.205346 0.455297 0.079 Uiso 1 1 calc R U . . .
C22 C 1.0812(5) 0.11998(14) 0.39935(15) 0.0721(8) Uani 1 1 d . . . . .
H22 H 1.205816 0.090566 0.411372 0.087 Uiso 1 1 calc R U . . .
C23 C 0.9278(5) 0.09488(13) 0.35656(14) 0.0731(8) Uani 1 1 d . . . . .
H23 H 0.944245 0.047834 0.338890 0.088 Uiso 1 1 calc R U . . .
C24 C 0.7466(5) 0.13962(11) 0.33931(12) 0.0585(6) Uani 1 1 d . . . . .
H24 H 0.636808 0.123418 0.310235 0.070 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 C6 1.214(2) . ?
O2 C19 1.211(2) . ?
N1 C5 1.335(2) . ?
N1 C1 1.336(3) . ?
N2 C20 1.340(3) . ?
N2 C21 1.342(3) . ?
C1 C2 1.379(3) . ?
C1 H1 0.9400 . ?
C2 C3 1.369(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.384(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.506(2) . ?
C6 C7 1.520(2) . ?
C7 C11 1.553(2) . ?
C7 C8 1.555(3) . ?
C7 H7 0.9900 . ?
C8 C10 1.525(3) . ?
C8 C9 1.525(3) . ?
C8 H8 0.9900 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C11 C12 1.524(3) . ?
C11 C18 1.533(3) . ?
C11 H11 0.9900 . ?
C12 C17 1.385(3) . ?
C12 C13 1.389(3) . ?
C13 C14 1.383(3) . ?
C13 H13 0.9400 . ?
C14 C15 1.377(3) . ?
C14 H14 0.9400 . ?
C15 C16 1.373(4) . ?
C15 H15 0.9400 . ?
C16 C17 1.387(3) . ?
C16 H16 0.9400 . ?
C17 H17 0.9400 . ?
C18 C19 1.506(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C19 C20 1.509(3) . ?
C20 C24 1.384(3) . ?
C21 C22 1.382(4) . ?
C21 H21 0.9400 . ?
C22 C23 1.359(4) . ?
C22 H22 0.9400 . ?
C23 C24 1.386(3) . ?
C23 H23 0.9400 . ?
C24 H24 0.9400 . ?

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 N1 C1 116.69(17) . . ?
C20 N2 C21 117.0(2) . . ?
N1 C1 C2 124.0(2) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C3 C2 C1 118.61(19) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 118.7(2) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C3 C4 C5 118.7(2) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 123.26(17) . . ?
N1 C5 C6 117.94(16) . . ?
C4 C5 C6 118.81(17) . . ?
O1 C6 C5 118.94(16) . . ?
O1 C6 C7 120.68(16) . . ?
C5 C6 C7 120.37(16) . . ?
C6 C7 C11 108.53(14) . . ?
C6 C7 C8 109.72(15) . . ?
C11 C7 C8 114.31(14) . . ?
C6 C7 H7 108.0 . . ?
C11 C7 H7 108.0 . . ?
C8 C7 H7 108.0 . . ?
C10 C8 C9 110.7(2) . . ?
C10 C8 C7 114.35(18) . . ?
C9 C8 C7 111.13(16) . . ?
C10 C8 H8 106.7 . . ?
C9 C8 H8 106.7 . . ?
C7 C8 H8 106.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C18 111.54(15) . . ?
C12 C11 C7 110.21(14) . . ?
C18 C11 C7 111.04(14) . . ?
C12 C11 H11 108.0 . . ?
C18 C11 H11 108.0 . . ?
C7 C11 H11 108.0 . . ?
C17 C12 C13 117.70(18) . . ?
C17 C12 C11 121.05(18) . . ?
C13 C12 C11 121.25(17) . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 118.9(2) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C17 120.5(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C12 C17 C16 121.2(2) . . ?
C12 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C19 C18 C11 113.99(16) . . ?
C19 C18 H18A 108.8 . . ?
C11 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C11 C18 H18B 108.8 . . ?
H18A C18 H18B 107.6 . . ?
O2 C19 C18 123.16(17) . . ?
O2 C19 C20 119.45(17) . . ?
C18 C19 C20 117.39(18) . . ?
N2 C20 C24 123.3(2) . . ?
N2 C20 C19 117.12(17) . . ?
C24 C20 C19 119.5(2) . . ?
N2 C21 C22 122.8(3) . . ?
N2 C21 H21 118.6 . . ?
C22 C21 H21 118.6 . . ?
C23 C22 C21 119.5(2) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 119.1(2) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
C20 C24 C23 118.2(3) . . ?
C20 C24 H24 120.9 . . ?
C23 C24 H24 120.9 . . ?

_refine_diff_density_max         0.142
_refine_diff_density_min         -0.113
_refine_diff_density_rms         0.027




