# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2103629'
loop_
_audit_author_name
_audit_author_address
'Cai Tao'
;xiamen university
China
;
_audit_update_record             
;
2021-08-17 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H21 N O2'
_chemical_formula_weight         355.42

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8259(3)
_cell_length_b                   9.8256(2)
_cell_length_c                   10.8672(3)
_cell_angle_alpha                97.864(2)
_cell_angle_beta                 108.797(2)
_cell_angle_gamma                103.162(2)
_cell_volume                     941.65(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    11380
_cell_measurement_theta_min      4.3940
_cell_measurement_theta_max      74.1990

_exptl_crystal_description       block
_exptl_crystal_colour            coloreless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.37791
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20561
_diffrn_reflns_av_R_equivalents  0.0917
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.41
_diffrn_reflns_theta_max         66.59
_reflns_number_total             3333
_reflns_number_gt                2887
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3333
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.2913
_refine_ls_wR_factor_gt          0.2185
_refine_ls_goodness_of_fit_ref   1.383
_refine_ls_restrained_S_all      1.383
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.78775(15) 0.29709(15) 0.11586(13) 0.0417(5) Uani 1 1 d . . .
O2 O 1.24101(14) 0.18526(14) 0.27215(13) 0.0389(5) Uani 1 1 d . . .
N1 N 1.00379(16) 0.19396(17) 0.25201(14) 0.0325(5) Uani 1 1 d . . .
H1A H 0.9547 0.2459 0.2788 0.039 Uiso 1 1 calc R . .
C1 C 1.21419(18) 0.38813(19) 0.40298(16) 0.0295(5) Uani 1 1 d . . .
C2 C 0.4898(2) 0.2267(2) -0.09330(18) 0.0321(5) Uani 1 1 d . . .
C3 C 1.31505(19) 0.5055(2) 0.39134(17) 0.0326(5) Uani 1 1 d . . .
C4 C 1.15868(19) 0.24738(19) 0.30372(16) 0.0304(5) Uani 1 1 d . . .
C5 C 0.78899(19) 0.05642(19) 0.06208(17) 0.0313(5) Uani 1 1 d . . .
H5A H 0.7322 -0.0332 0.0065 0.038 Uiso 1 1 calc R . .
C6 C 0.91976(19) 0.06434(19) 0.16087(16) 0.0296(5) Uani 1 1 d . . .
C7 C 0.73160(19) 0.17809(19) 0.03715(17) 0.0308(5) Uani 1 1 d . . .
C8 C 0.96802(19) -0.0651(2) 0.18096(17) 0.0322(5) Uani 1 1 d . . .
C9 C 0.3746(2) 0.2043(2) -0.2161(2) 0.0396(5) Uani 1 1 d . . .
H9A H 0.3000 0.2495 -0.2215 0.048 Uiso 1 1 calc R . .
C10 C 0.59948(19) 0.15495(19) -0.08924(16) 0.0307(5) Uani 1 1 d . . .
C11 C 0.9347(2) -0.1780(2) 0.07372(19) 0.0374(5) Uani 1 1 d . . .
H11A H 0.8872 -0.1696 -0.0128 0.045 Uiso 1 1 calc R . .
C12 C 1.1630(2) 0.3969(2) 0.50932(18) 0.0367(5) Uani 1 1 d . . .
H12A H 1.0939 0.3178 0.5145 0.044 Uiso 1 1 calc R . .
C13 C 0.5916(2) 0.0654(2) -0.20355(18) 0.0386(5) Uani 1 1 d . . .
H13A H 0.6643 0.0179 -0.1990 0.046 Uiso 1 1 calc R . .
C14 C 1.04087(19) -0.0799(2) 0.31089(19) 0.0385(5) Uani 1 1 d . . .
H14A H 1.0641 -0.0052 0.3837 0.046 Uiso 1 1 calc R . .
C15 C 1.2147(2) 0.5225(2) 0.60660(19) 0.0436(6) Uani 1 1 d . . .
H15A H 1.1823 0.5278 0.6782 0.052 Uiso 1 1 calc R . .
C16 C 1.3648(2) 0.6324(2) 0.4905(2) 0.0407(5) Uani 1 1 d . . .
H16A H 1.4324 0.7128 0.4853 0.049 Uiso 1 1 calc R . .
C17 C 1.3688(2) 0.5049(2) 0.2766(2) 0.0423(5) Uani 1 1 d . . .
H17A H 1.3260 0.4116 0.2172 0.063 Uiso 1 1 calc R . .
H17B H 1.4764 0.5277 0.3099 0.063 Uiso 1 1 calc R . .
H17C H 1.3385 0.5752 0.2293 0.063 Uiso 1 1 calc R . .
C18 C 1.3147(2) 0.6398(2) 0.59622(19) 0.0421(6) Uani 1 1 d . . .
H18A H 1.3490 0.7249 0.6609 0.051 Uiso 1 1 calc R . .
C19 C 0.4884(2) 0.3186(2) 0.0274(2) 0.0426(6) Uani 1 1 d . . .
H19A H 0.4051 0.3579 0.0021 0.064 Uiso 1 1 calc R . .
H19B H 0.5804 0.3954 0.0667 0.064 Uiso 1 1 calc R . .
H19C H 0.4788 0.2618 0.0909 0.064 Uiso 1 1 calc R . .
C20 C 0.4761(3) 0.0464(2) -0.32431(19) 0.0456(6) Uani 1 1 d . . .
H20A H 0.4711 -0.0132 -0.4008 0.055 Uiso 1 1 calc R . .
C21 C 0.9719(2) -0.3035(2) 0.0951(2) 0.0487(6) Uani 1 1 d . . .
H21A H 0.9485 -0.3788 0.0227 0.058 Uiso 1 1 calc R . .
C22 C 1.0781(2) -0.2043(3) 0.3310(2) 0.0494(6) Uani 1 1 d . . .
H22A H 1.1266 -0.2128 0.4173 0.059 Uiso 1 1 calc R . .
C23 C 0.3682(2) 0.1171(2) -0.3299(2) 0.0467(6) Uani 1 1 d . . .
H23A H 0.2909 0.1056 -0.4107 0.056 Uiso 1 1 calc R . .
C24 C 1.0437(3) -0.3169(3) 0.2236(3) 0.0544(7) Uani 1 1 d . . .
H24A H 1.0685 -0.4008 0.2377 0.065 Uiso 1 1 calc R . .


_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 C7 1.238(2) . ?
O2 C4 1.221(2) . ?
N1 C4 1.383(2) . ?
N1 C6 1.391(2) . ?
C1 C3 1.389(3) . ?
C1 C12 1.401(3) . ?
C1 C4 1.498(2) . ?
C2 C9 1.394(3) . ?
C2 C10 1.409(2) . ?
C2 C19 1.493(3) . ?
C3 C16 1.404(3) . ?
C3 C17 1.503(3) . ?
C5 C6 1.361(2) . ?
C5 C7 1.455(2) . ?
C6 C8 1.475(2) . ?
C7 C10 1.501(2) . ?
C8 C11 1.389(3) . ?
C8 C14 1.407(2) . ?
C9 C23 1.379(3) . ?
C10 C13 1.390(3) . ?
C11 C21 1.392(3) . ?
C12 C15 1.382(3) . ?
C13 C20 1.387(3) . ?
C14 C22 1.379(3) . ?
C15 C18 1.378(3) . ?
C16 C18 1.388(3) . ?
C20 C23 1.384(3) . ?
C21 C24 1.387(3) . ?
C22 C24 1.387(4) . ?

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
C4 N1 C6 126.26(15) . . ?
C3 C1 C12 121.02(17) . . ?
C3 C1 C4 121.13(16) . . ?
C12 C1 C4 117.84(17) . . ?
C9 C2 C10 117.25(17) . . ?
C9 C2 C19 119.49(16) . . ?
C10 C2 C19 123.21(15) . . ?
C1 C3 C16 117.63(18) . . ?
C1 C3 C17 123.56(17) . . ?
C16 C3 C17 118.77(18) . . ?
O2 C4 N1 123.27(16) . . ?
O2 C4 C1 123.82(15) . . ?
N1 C4 C1 112.91(14) . . ?
C6 C5 C7 124.71(16) . . ?
C5 C6 N1 119.87(16) . . ?
C5 C6 C8 121.16(16) . . ?
N1 C6 C8 118.73(14) . . ?
O1 C7 C5 122.28(14) . . ?
O1 C7 C10 120.19(15) . . ?
C5 C7 C10 117.53(14) . . ?
C11 C8 C14 118.76(17) . . ?
C11 C8 C6 121.05(15) . . ?
C14 C8 C6 120.07(17) . . ?
C23 C9 C2 121.82(17) . . ?
C13 C10 C2 120.86(16) . . ?
C13 C10 C7 118.14(15) . . ?
C2 C10 C7 120.94(15) . . ?
C8 C11 C21 120.38(18) . . ?
C15 C12 C1 120.4(2) . . ?
C20 C13 C10 120.34(18) . . ?
C22 C14 C8 120.45(19) . . ?
C18 C15 C12 119.19(19) . . ?
C18 C16 C3 121.0(2) . . ?
C15 C18 C16 120.80(18) . . ?
C23 C20 C13 119.37(18) . . ?
C24 C21 C11 120.4(2) . . ?
C14 C22 C24 120.52(19) . . ?
C9 C23 C20 120.34(17) . . ?
C22 C24 C21 119.51(19) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        66.59
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.191
