# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_Compound_1
_database_code_depnum_ccdc_archive 'CCDC 2207715'
loop_
_audit_author_name
_audit_author_address
'Koichiro Omasa'
;Tokyo Metropolitan University
Japan
;
_audit_update_record             
;
2022-09-16 deposited with the CCDC.	2022-10-31 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         ?
_chemical_formula_sum            'C31 H23 N O3'
_chemical_formula_weight         457.50

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'
N N 0.0311 0.0180 '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      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                   10.7112(4)
_cell_length_b                   7.8141(3)
_cell_length_c                   27.003(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.978(5)
_cell_angle_gamma                90
_cell_volume                     2258.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8664
_cell_measurement_theta_min      5.89
_cell_measurement_theta_max      72.36

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.688
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.6628
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            18073
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         4.390
_diffrn_reflns_theta_max         72.356
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.895
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.895
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.895
_reflns_number_total             4399
_reflns_number_gt                4005
_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)+(0.1207P)²+0.4417P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4399
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1674
_refine_ls_wR_factor_gt          0.1603
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_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
O001 O 0.92238(9) 0.23656(12) 0.49556(3) 0.0258(3) Uani 1 1 d . . . . .
O002 O 0.56319(10) 0.22164(15) 0.58498(4) 0.0339(3) Uani 1 1 d . . . . .
H1 H 0.489(3) 0.182(3) 0.5888(8) 0.051 Uiso 1 1 d . U . . .
O003 O 0.33766(11) 0.10790(16) 0.56231(5) 0.0435(3) Uani 1 1 d . . . . .
N004 N 1.14852(11) 0.05660(15) 0.41482(4) 0.0284(3) Uani 1 1 d . . . . .
C005 C 0.77771(12) 0.45876(17) 0.59739(5) 0.0249(3) Uani 1 1 d . . . . .
H005 H 0.696003 0.486882 0.607333 0.030 Uiso 1 1 calc R U . . .
C006 C 0.91280(12) 0.32736(16) 0.53854(5) 0.0233(3) Uani 1 1 d . . . . .
C007 C 1.04534(12) 0.19885(17) 0.47999(5) 0.0242(3) Uani 1 1 d . . . . .
H00A H 1.088458 0.123554 0.504606 0.029 Uiso 1 1 calc R U . . .
H00B H 1.094031 0.306024 0.477531 0.029 Uiso 1 1 calc R U . . .
C008 C 0.87982(12) 0.50494(16) 0.62831(5) 0.0246(3) Uani 1 1 d . . . . .
C009 C 0.79121(12) 0.37293(17) 0.55248(5) 0.0240(3) Uani 1 1 d . . . . .
C00A C 0.99857(13) 0.46259(18) 0.61225(5) 0.0264(3) Uani 1 1 d . . . . .
H00C H 1.069888 0.496054 0.631783 0.032 Uiso 1 1 calc R U . . .
C00B C 0.68177(12) 0.33183(17) 0.51907(5) 0.0257(3) Uani 1 1 d . . . . .
C00C C 1.03729(13) 0.11112(16) 0.43025(5) 0.0248(3) Uani 1 1 d . . . . .
C00D C 1.01526(12) 0.37336(17) 0.56872(5) 0.0255(3) Uani 1 1 d . . . . .
H00D H 1.097111 0.343326 0.559393 0.031 Uiso 1 1 calc R U . . .
C00E C 0.68651(12) 0.36624(17) 0.46850(5) 0.0264(3) Uani 1 1 d . . . . .
H00E H 0.758709 0.421840 0.456851 0.032 Uiso 1 1 calc R U . . .
C00F C 0.57242(13) 0.25650(18) 0.53623(5) 0.0275(3) Uani 1 1 d . . . . .
C00G C 0.86512(13) 0.59291(17) 0.67683(5) 0.0266(3) Uani 1 1 d . . . . .
C00H C 0.47422(13) 0.21371(19) 0.50192(6) 0.0304(3) Uani 1 1 d . . . . .
C00I C 1.14981(15) -0.01965(19) 0.37053(5) 0.0317(3) Uani 1 1 d . . . . .
H00I H 1.227592 -0.059591 0.359218 0.038 Uiso 1 1 calc R U . . .
C00J C 0.59101(13) 0.32365(18) 0.43376(5) 0.0292(3) Uani 1 1 d . . . . .
C00K C 0.92638(14) 0.09071(19) 0.40299(5) 0.0303(3) Uani 1 1 d . . . . .
H00K H 0.849450 0.129560 0.415394 0.036 Uiso 1 1 calc R U . . .
C00L C 0.75442(14) 0.67566(19) 0.68874(5) 0.0322(3) Uani 1 1 d . . . . .
H00L H 0.686225 0.676607 0.665295 0.039 Uiso 1 1 calc R U . . .
C00M C 0.48494(13) 0.24537(19) 0.45127(6) 0.0310(3) Uani 1 1 d . . . . .
H00M H 0.419144 0.213050 0.428690 0.037 Uiso 1 1 calc R U . . .
C00N C 0.61008(13) 0.3565(2) 0.38017(5) 0.0328(3) Uani 1 1 d . . . . .
C00O C 1.04433(16) -0.0439(2) 0.34013(5) 0.0352(4) Uani 1 1 d . . . . .
H00O H 1.049809 -0.097138 0.308652 0.042 Uiso 1 1 calc R U . . .
C00P C 0.93087(16) 0.0119(2) 0.35704(6) 0.0368(4) Uani 1 1 d . . . . .
H00P H 0.856544 -0.003713 0.337334 0.044 Uiso 1 1 calc R U . . .
C00Q C 0.95051(16) 0.6756(2) 0.75798(6) 0.0384(4) Uani 1 1 d . . . . .
H00Q H 1.018366 0.674991 0.781587 0.046 Uiso 1 1 calc R U . . .
C00R C 0.96298(14) 0.5954(2) 0.71251(5) 0.0329(3) Uani 1 1 d . . . . .
H00R H 1.039673 0.540942 0.705478 0.039 Uiso 1 1 calc R U . . .
C00S C 0.74195(16) 0.7565(2) 0.73410(6) 0.0377(4) Uani 1 1 d . . . . .
H00S H 0.665789 0.812232 0.741185 0.045 Uiso 1 1 calc R U . . .
C00T C 0.36071(14) 0.1320(2) 0.51854(6) 0.0362(4) Uani 1 1 d . . . . .
H00T H 0.300810 0.095147 0.494061 0.043 Uiso 1 1 calc R U . . .
C00U C 0.83979(17) 0.7566(2) 0.76919(6) 0.0383(4) Uani 1 1 d . . . . .
H00U H 0.831055 0.811192 0.800318 0.046 Uiso 1 1 calc R U . . .
C00V C 0.66310(15) 0.5097(2) 0.36475(6) 0.0363(4) Uani 1 1 d . . . . .
H00V H 0.682816 0.596315 0.388435 0.044 Uiso 1 1 calc R U . . .
C00W C 0.58051(16) 0.2321(2) 0.34455(6) 0.0425(4) Uani 1 1 d . . . . .
H00W H 0.543352 0.127383 0.354208 0.051 Uiso 1 1 calc R U . . .
C00X C 0.68751(16) 0.5372(3) 0.31504(6) 0.0453(4) Uani 1 1 d . . . . .
H00X H 0.723706 0.642036 0.304986 0.054 Uiso 1 1 calc R U . . .
C00Y C 0.60531(19) 0.2608(3) 0.29486(7) 0.0536(5) Uani 1 1 d . . . . .
H00Y H 0.584925 0.175313 0.270892 0.064 Uiso 1 1 calc R U . . .
C00Z C 0.65892(18) 0.4114(3) 0.28025(6) 0.0534(5) Uani 1 1 d . . . . .
H00Z H 0.676374 0.429346 0.246390 0.064 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
O001 C006 1.3672(16) . ?
O001 C007 1.4270(16) . ?
O002 C00F 1.3512(18) . ?
O003 C00T 1.230(2) . ?
N004 C00I 1.3366(19) . ?
N004 C00C 1.3449(18) . ?
C005 C009 1.3976(19) . ?
C005 C008 1.4001(19) . ?
C006 C00D 1.3914(19) . ?
C006 C009 1.4137(18) . ?
C007 C00C 1.5079(18) . ?
C008 C00A 1.3977(19) . ?
C008 C00G 1.4927(19) . ?
C009 C00B 1.4894(18) . ?
C00A C00D 1.3834(19) . ?
C00B C00E 1.395(2) . ?
C00B C00F 1.404(2) . ?
C00C C00K 1.385(2) . ?
C00E C00J 1.4038(19) . ?
C00F C00H 1.418(2) . ?
C00G C00L 1.398(2) . ?
C00G C00R 1.399(2) . ?
C00H C00M 1.398(2) . ?
C00H C00T 1.458(2) . ?
C00I C00O 1.386(2) . ?
C00J C00M 1.388(2) . ?
C00J C00N 1.491(2) . ?
C00K C00P 1.388(2) . ?
C00L C00S 1.389(2) . ?
C00N C00V 1.395(2) . ?
C00N C00W 1.396(2) . ?
C00O C00P 1.383(2) . ?
C00Q C00U 1.387(3) . ?
C00Q C00R 1.389(2) . ?
C00S C00U 1.388(3) . ?
C00V C00X 1.393(2) . ?
C00W C00Y 1.395(3) . ?
C00X C00Z 1.387(3) . ?
C00Y C00Z 1.373(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
C006 O001 C007 117.02(10) . . ?
C00I N004 C00C 117.06(12) . . ?
C009 C005 C008 122.61(12) . . ?
O001 C006 C00D 123.40(12) . . ?
O001 C006 C009 116.98(11) . . ?
C00D C006 C009 119.61(12) . . ?
O001 C007 C00C 109.35(11) . . ?
C00A C008 C005 117.03(12) . . ?
C00A C008 C00G 120.40(12) . . ?
C005 C008 C00G 122.56(12) . . ?
C005 C009 C006 118.41(12) . . ?
C005 C009 C00B 121.75(12) . . ?
C006 C009 C00B 119.83(12) . . ?
C00D C00A C008 121.91(12) . . ?
C00E C00B C00F 117.59(12) . . ?
C00E C00B C009 119.81(12) . . ?
C00F C00B C009 122.59(12) . . ?
N004 C00C C00K 123.48(12) . . ?
N004 C00C C007 113.32(12) . . ?
C00K C00C C007 123.19(12) . . ?
C00A C00D C006 120.35(12) . . ?
C00B C00E C00J 123.94(13) . . ?
O002 C00F C00B 119.74(12) . . ?
O002 C00F C00H 120.77(13) . . ?
C00B C00F C00H 119.46(13) . . ?
C00L C00G C00R 117.16(13) . . ?
C00L C00G C008 122.07(13) . . ?
C00R C00G C008 120.77(13) . . ?
C00M C00H C00F 120.89(13) . . ?
C00M C00H C00T 118.43(13) . . ?
C00F C00H C00T 120.66(14) . . ?
N004 C00I C00O 123.87(14) . . ?
C00M C00J C00E 117.59(13) . . ?
C00M C00J C00N 123.22(13) . . ?
C00E C00J C00N 119.12(13) . . ?
C00C C00K C00P 118.09(13) . . ?
C00S C00L C00G 121.44(14) . . ?
C00J C00M C00H 120.46(13) . . ?
C00V C00N C00W 118.50(15) . . ?
C00V C00N C00J 120.57(14) . . ?
C00W C00N C00J 120.87(15) . . ?
C00P C00O C00I 117.95(13) . . ?
C00O C00P C00K 119.53(14) . . ?
C00U C00Q C00R 120.52(15) . . ?
C00Q C00R C00G 121.48(14) . . ?
C00U C00S C00L 120.59(14) . . ?
O003 C00T C00H 124.07(14) . . ?
C00Q C00U C00S 118.80(13) . . ?
C00X C00V C00N 120.80(16) . . ?
C00Y C00W C00N 120.29(18) . . ?
C00Z C00X C00V 119.93(19) . . ?
C00Z C00Y C00W 120.62(18) . . ?
C00Y C00Z C00X 119.85(16) . . ?

_refine_diff_density_max         0.410
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.074

