# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_mo_dd20173_0m
_database_code_depnum_ccdc_archive 'CCDC 2032715'
loop_
_audit_author_name
_audit_author_address
dd
;Wenzhou University
China
;
_audit_update_record             
;
2020-09-18 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H21 N O'
_chemical_formula_weight         339.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, 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                   22.6175(15)
_cell_length_b                   14.6158(8)
_cell_length_c                   11.7728(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.296(2)
_cell_angle_gamma                90
_cell_volume                     3829.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6501
_cell_measurement_theta_min      4.602
_cell_measurement_theta_max      51.908

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6324
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            18866
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.667
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3769
_reflns_number_gt                2627
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0555P)²+1.5668P] 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     SHELXL
_refine_ls_extinction_coef       0.0057(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3769
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1335
_refine_ls_wR_factor_gt          0.1132
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.004
_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 0.41136(5) 0.85446(7) 0.25259(10) 0.0572(3) Uani 1 1 d . . . . .
N1 N 0.34584(6) 0.75587(9) 0.15729(12) 0.0588(4) Uani 1 1 d . . . . .
C1 C 0.36745(8) 0.83795(11) 0.15989(14) 0.0550(4) Uani 1 1 d . . . . .
C2 C 0.37749(8) 0.71315(11) 0.25574(14) 0.0535(4) Uani 1 1 d . . . . .
C3 C 0.41756(8) 0.77301(11) 0.31408(14) 0.0531(4) Uani 1 1 d . . . . .
C4 C 0.46085(8) 0.77298(12) 0.42143(14) 0.0564(4) Uani 1 1 d . . . . .
C5 C 0.46919(9) 0.69603(13) 0.49148(16) 0.0682(5) Uani 1 1 d . . . . .
H5 H 0.4482 0.6426 0.4680 0.082 Uiso 1 1 calc R U . . .
C6 C 0.50824(11) 0.69801(17) 0.59527(18) 0.0859(7) Uani 1 1 d . . . . .
H6 H 0.5135 0.6458 0.6412 0.103 Uiso 1 1 calc R U . . .
C7 C 0.53960(10) 0.77596(19) 0.63190(19) 0.0890(7) Uani 1 1 d . . . . .
H7 H 0.5654 0.7770 0.7029 0.107 Uiso 1 1 calc R U . . .
C8 C 0.53273(10) 0.85253(17) 0.56333(19) 0.0862(7) Uani 1 1 d . . . . .
H8 H 0.5543 0.9054 0.5874 0.103 Uiso 1 1 calc R U . . .
C9 C 0.49389(9) 0.85106(14) 0.45877(18) 0.0736(6) Uani 1 1 d . . . . .
H9 H 0.4897 0.9031 0.4125 0.088 Uiso 1 1 calc R U . . .
C10 C 0.34978(8) 0.91230(11) 0.07850(15) 0.0569(4) Uani 1 1 d . . . . .
C11 C 0.37215(9) 1.00005(13) 0.10026(18) 0.0724(6) Uani 1 1 d . . . . .
H11 H 0.3986 1.0128 0.1684 0.087 Uiso 1 1 calc R U . . .
C12 C 0.35499(11) 1.06839(14) 0.0202(2) 0.0856(7) Uani 1 1 d . . . . .
H12 H 0.3696 1.1275 0.0352 0.103 Uiso 1 1 calc R U . . .
C13 C 0.31665(11) 1.04998(16) -0.0809(2) 0.0853(7) Uani 1 1 d . . . . .
H13 H 0.3059 1.0963 -0.1348 0.102 Uiso 1 1 calc R U . . .
C14 C 0.29403(11) 0.96345(16) -0.10294(18) 0.0819(6) Uani 1 1 d . . . . .
H14 H 0.2677 0.9512 -0.1714 0.098 Uiso 1 1 calc R U . . .
C15 C 0.31042(9) 0.89446(13) -0.02305(16) 0.0681(5) Uani 1 1 d . . . . .
H15 H 0.2949 0.8359 -0.0378 0.082 Uiso 1 1 calc R U . . .
C16 C 0.36347(8) 0.61687(11) 0.28054(14) 0.0534(4) Uani 1 1 d . . . . .
C17 C 0.38459(8) 0.54612(12) 0.21872(15) 0.0572(4) Uani 1 1 d . . . . .
C18 C 0.36780(9) 0.45707(12) 0.23865(16) 0.0649(5) Uani 1 1 d . . . . .
H18 H 0.3815 0.4098 0.1973 0.078 Uiso 1 1 calc R U . . .
C19 C 0.33138(8) 0.43606(12) 0.31780(17) 0.0650(5) Uani 1 1 d . . . . .
C20 C 0.31180(8) 0.50686(12) 0.37860(17) 0.0667(5) Uani 1 1 d . . . . .
H20 H 0.2878 0.4936 0.4329 0.080 Uiso 1 1 calc R U . . .
C21 C 0.32661(8) 0.59733(11) 0.36166(15) 0.0605(5) Uani 1 1 d . . . . .
C22 C 0.30248(11) 0.67255(14) 0.4284(2) 0.0875(7) Uani 1 1 d . . . . .
H22A H 0.3354 0.7052 0.4734 0.131 Uiso 1 1 calc R U . . .
H22B H 0.2780 0.6464 0.4787 0.131 Uiso 1 1 calc R U . . .
H22C H 0.2787 0.7139 0.3755 0.131 Uiso 1 1 calc R U . . .
C23 C 0.42433(10) 0.56591(14) 0.13193(17) 0.0779(6) Uani 1 1 d . . . . .
H23A H 0.4018 0.5987 0.0678 0.117 Uiso 1 1 calc R U . . .
H23B H 0.4386 0.5094 0.1052 0.117 Uiso 1 1 calc R U . . .
H23C H 0.4579 0.6023 0.1674 0.117 Uiso 1 1 calc R U . . .
C24 C 0.31340(10) 0.33860(13) 0.3373(2) 0.0898(7) Uani 1 1 d . . . . .
H24A H 0.3218 0.3007 0.2756 0.135 Uiso 1 1 calc R U . . .
H24B H 0.2712 0.3363 0.3395 0.135 Uiso 1 1 calc R U . . .
H24C H 0.3357 0.3169 0.4093 0.135 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 C1 1.359(2) . ?
O1 C3 1.3873(18) . ?
N1 C1 1.294(2) . ?
N1 C2 1.396(2) . ?
C1 C10 1.457(2) . ?
C2 C3 1.355(2) . ?
C2 C16 1.483(2) . ?
C3 C4 1.454(2) . ?
C4 C5 1.387(2) . ?
C4 C9 1.391(3) . ?
C5 C6 1.374(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.370(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.372(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.379(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C15 1.382(3) . ?
C10 C11 1.386(2) . ?
C11 C12 1.380(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.397(2) . ?
C16 C21 1.405(2) . ?
C17 C18 1.388(2) . ?
C17 C23 1.505(3) . ?
C18 C19 1.384(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.376(3) . ?
C19 C24 1.510(2) . ?
C20 C21 1.387(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.509(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
C1 O1 C3 104.93(12) . . ?
C1 N1 C2 105.05(14) . . ?
N1 C1 O1 113.72(14) . . ?
N1 C1 C10 128.18(17) . . ?
O1 C1 C10 118.08(15) . . ?
C3 C2 N1 109.23(14) . . ?
C3 C2 C16 131.30(15) . . ?
N1 C2 C16 119.47(15) . . ?
C2 C3 O1 107.07(14) . . ?
C2 C3 C4 136.55(15) . . ?
O1 C3 C4 116.32(14) . . ?
C5 C4 C9 117.96(18) . . ?
C5 C4 C3 121.05(16) . . ?
C9 C4 C3 120.97(16) . . ?
C6 C5 C4 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C7 C6 C5 120.8(2) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 119.7(2) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 120.0(2) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C4 121.0(2) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
C15 C10 C11 119.48(17) . . ?
C15 C10 C1 119.14(16) . . ?
C11 C10 C1 121.38(18) . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.19(19) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 119.9(2) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C10 C15 C14 120.23(19) . . ?
C10 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C21 120.23(15) . . ?
C17 C16 C2 119.65(15) . . ?
C21 C16 C2 120.04(15) . . ?
C18 C17 C16 118.47(17) . . ?
C18 C17 C23 120.66(17) . . ?
C16 C17 C23 120.86(16) . . ?
C19 C18 C17 122.41(18) . . ?
C19 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
C20 C19 C18 117.97(16) . . ?
C20 C19 C24 120.65(19) . . ?
C18 C19 C24 121.38(19) . . ?
C19 C20 C21 122.26(18) . . ?
C19 C20 H20 118.9 . . ?
C21 C20 H20 118.9 . . ?
C20 C21 C16 118.66(17) . . ?
C20 C21 C22 120.04(17) . . ?
C16 C21 C22 121.30(15) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C17 C23 H23A 109.5 . . ?
C17 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C17 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
C2 N1 C1 O1 -0.04(19) . . . . ?
C2 N1 C1 C10 -178.87(16) . . . . ?
C3 O1 C1 N1 0.10(18) . . . . ?
C3 O1 C1 C10 179.07(14) . . . . ?
C1 N1 C2 C3 -0.05(18) . . . . ?
C1 N1 C2 C16 179.48(15) . . . . ?
N1 C2 C3 O1 0.11(18) . . . . ?
C16 C2 C3 O1 -179.35(16) . . . . ?
N1 C2 C3 C4 177.04(18) . . . . ?
C16 C2 C3 C4 -2.4(3) . . . . ?
C1 O1 C3 C2 -0.12(17) . . . . ?
C1 O1 C3 C4 -177.77(14) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
O1 C3 C4 C5 177.91(15) . . . . ?
C2 C3 C4 C9 -176.9(2) . . . . ?
O1 C3 C4 C9 -0.1(2) . . . . ?
C9 C4 C5 C6 1.0(3) . . . . ?
C3 C4 C5 C6 -177.06(17) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C5 C6 C7 C8 -1.1(4) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C7 C8 C9 C4 0.5(3) . . . . ?
C5 C4 C9 C8 -1.4(3) . . . . ?
C3 C4 C9 C8 176.71(18) . . . . ?
N1 C1 C10 C15 -8.7(3) . . . . ?
O1 C1 C10 C15 172.52(15) . . . . ?
N1 C1 C10 C11 172.09(18) . . . . ?
O1 C1 C10 C11 -6.7(2) . . . . ?
C15 C10 C11 C12 -0.1(3) . . . . ?
C1 C10 C11 C12 179.08(18) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C14 1.1(3) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C11 C10 C15 C14 0.7(3) . . . . ?
C1 C10 C15 C14 -178.52(17) . . . . ?
C13 C14 C15 C10 -0.4(3) . . . . ?
C3 C2 C16 C17 -103.8(2) . . . . ?
N1 C2 C16 C17 76.8(2) . . . . ?
C3 C2 C16 C21 79.4(2) . . . . ?
N1 C2 C16 C21 -99.98(19) . . . . ?
C21 C16 C17 C18 0.7(3) . . . . ?
C2 C16 C17 C18 -176.14(15) . . . . ?
C21 C16 C17 C23 -179.72(17) . . . . ?
C2 C16 C17 C23 3.5(3) . . . . ?
C16 C17 C18 C19 -0.4(3) . . . . ?
C23 C17 C18 C19 179.93(17) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
C17 C18 C19 C24 179.59(18) . . . . ?
C18 C19 C20 C21 1.0(3) . . . . ?
C24 C19 C20 C21 -178.96(18) . . . . ?
C19 C20 C21 C16 -0.8(3) . . . . ?
C19 C20 C21 C22 178.30(19) . . . . ?
C17 C16 C21 C20 -0.1(3) . . . . ?
C2 C16 C21 C20 176.72(16) . . . . ?
C17 C16 C21 C22 -179.14(18) . . . . ?
C2 C16 C21 C22 -2.4(3) . . . . ?

_refine_diff_density_max         0.146
_refine_diff_density_min         -0.115
_refine_diff_density_rms         0.028

_shelxl_version_number           2013-4

