# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_ddz20012_0m
_database_code_depnum_ccdc_archive 'CCDC 2034501'
loop_
_audit_author_name
_audit_author_address
'Jing-Yuan Ge'
;Wenzhou University
China
;
_audit_update_record             
;
2020-09-29 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H15 N3 O'
_chemical_formula_weight         349.38

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   5.9943(19)
_cell_length_b                   8.485(3)
_cell_length_c                   16.919(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.844(10)
_cell_angle_gamma                90
_cell_volume                     860.4(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2745
_cell_measurement_theta_min      4.816
_cell_measurement_theta_max      51.637

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6218
_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            13108
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.408
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3204
_reflns_number_gt                2081
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.863
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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)+(0.0714P)²+0.0263P] 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       0.059(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 724 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -1.1(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3204
_refine_ls_number_parameters     245
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1574
_refine_ls_wR_factor_gt          0.1299
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.6187(6) 0.1631(5) 0.3685(2) 0.0783(12) Uani 1 1 d . . . . .
N1 N 0.7551(6) 0.4593(4) 0.1846(2) 0.0501(10) Uani 1 1 d . . . . .
N2 N 0.5396(7) 0.3839(4) 0.2965(2) 0.0492(10) Uani 1 1 d . . . . .
N3 N 0.2602(6) 0.6363(5) 0.2642(2) 0.0493(10) Uani 1 1 d . . . . .
C1 C 0.6722(9) 0.2483(6) 0.3137(3) 0.0569(13) Uani 1 1 d . . . . .
C2 C 0.8591(8) 0.2280(6) 0.2626(3) 0.0538(12) Uani 1 1 d . . . . .
C3 C 1.0086(10) 0.1028(7) 0.2764(4) 0.0694(15) Uani 1 1 d . . . . .
H3 H 0.9856 0.0337 0.3181 0.083 Uiso 1 1 calc R U . . .
C4 C 1.1878(10) 0.0831(7) 0.2283(4) 0.0763(17) Uani 1 1 d . . . . .
H4 H 1.2883 0.0015 0.2378 0.092 Uiso 1 1 calc R U . . .
C5 C 1.2192(9) 0.1849(8) 0.1655(4) 0.0740(17) Uani 1 1 d . . . . .
H5 H 1.3397 0.1694 0.1324 0.089 Uiso 1 1 calc R U . . .
C6 C 1.0772(8) 0.3072(7) 0.1512(3) 0.0616(14) Uani 1 1 d . . . . .
H6 H 1.1023 0.3749 0.1090 0.074 Uiso 1 1 calc R U . . .
C7 C 0.8922(8) 0.3315(6) 0.2003(3) 0.0514(12) Uani 1 1 d . . . . .
C8 C 0.5872(8) 0.4816(6) 0.2322(3) 0.0464(11) Uani 1 1 d . . . . .
C9 C 0.4332(7) 0.6113(5) 0.2196(3) 0.0444(11) Uani 1 1 d . . . . .
C10 C 0.3578(8) 0.4143(6) 0.3431(3) 0.0523(13) Uani 1 1 d . . . . .
H10 H 0.3284 0.3484 0.3856 0.063 Uiso 1 1 calc R U . . .
C11 C 0.2217(8) 0.5379(5) 0.3284(3) 0.0468(12) Uani 1 1 d . . . . .
C12 C 0.0267(8) 0.5757(6) 0.3771(3) 0.0489(12) Uani 1 1 d . . . . .
C13 C -0.0292(9) 0.4892(8) 0.4437(3) 0.0686(16) Uani 1 1 d . . . . .
H13 H 0.0597 0.4046 0.4593 0.082 Uiso 1 1 calc R U . . .
C14 C -0.2150(10) 0.5272(8) 0.4869(3) 0.0767(18) Uani 1 1 d . . . . .
H14 H -0.2506 0.4677 0.5311 0.092 Uiso 1 1 calc R U . . .
C15 C -0.3473(9) 0.6514(8) 0.4653(3) 0.0726(17) Uani 1 1 d . . . . .
H15 H -0.4730 0.6759 0.4945 0.087 Uiso 1 1 calc R U . . .
C16 C -0.2941(9) 0.7405(7) 0.4002(3) 0.0669(15) Uani 1 1 d . . . . .
H16 H -0.3828 0.8258 0.3856 0.080 Uiso 1 1 calc R U . . .
C17 C -0.1085(8) 0.7027(6) 0.3566(3) 0.0551(13) Uani 1 1 d . . . . .
H17 H -0.0734 0.7633 0.3127 0.066 Uiso 1 1 calc R U . . .
C18 C 0.4598(8) 0.7173(6) 0.1506(2) 0.0483(12) Uani 1 1 d . . . . .
C19 C 0.2786(9) 0.7407(6) 0.1003(3) 0.0610(14) Uani 1 1 d . . . . .
H19 H 0.1438 0.6907 0.1102 0.073 Uiso 1 1 calc R U . . .
C20 C 0.2979(11) 0.8383(8) 0.0354(3) 0.0782(17) Uani 1 1 d . . . . .
H20 H 0.1781 0.8498 0.0004 0.094 Uiso 1 1 calc R U . . .
C21 C 0.4936(13) 0.9188(8) 0.0223(3) 0.086(2) Uani 1 1 d . . . . .
H21 H 0.5056 0.9852 -0.0212 0.103 Uiso 1 1 calc R U . . .
C22 C 0.6703(11) 0.9004(7) 0.0736(4) 0.0859(19) Uani 1 1 d . . . . .
H22 H 0.8009 0.9572 0.0660 0.103 Uiso 1 1 calc R U . . .
C23 C 0.6551(9) 0.7980(7) 0.1366(3) 0.0670(16) Uani 1 1 d . . . . .
H23 H 0.7780 0.7831 0.1699 0.080 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 1.222(6) . ?
N1 C8 1.312(5) . ?
N1 C7 1.384(6) . ?
N2 C10 1.380(5) . ?
N2 C8 1.400(5) . ?
N2 C1 1.426(6) . ?
N3 C9 1.309(6) . ?
N3 C11 1.392(5) . ?
C1 C2 1.436(7) . ?
C2 C7 1.388(7) . ?
C2 C3 1.407(7) . ?
C3 C4 1.367(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.361(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.410(6) . ?
C6 H6 0.9300 . ?
C8 C9 1.451(6) . ?
C9 C18 1.484(6) . ?
C10 C11 1.349(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.475(6) . ?
C12 C17 1.389(6) . ?
C12 C13 1.389(6) . ?
C13 C14 1.379(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.365(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(6) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C23 1.380(7) . ?
C18 C19 1.384(6) . ?
C19 C20 1.382(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(9) . ?
C20 H20 0.9300 . ?
C21 C22 1.369(9) . ?
C21 H21 0.9300 . ?
C22 C23 1.379(7) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

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
C8 N1 C7 117.0(4) . . ?
C10 N2 C8 120.4(4) . . ?
C10 N2 C1 118.5(4) . . ?
C8 N2 C1 121.1(4) . . ?
C9 N3 C11 119.6(4) . . ?
O1 C1 N2 118.7(5) . . ?
O1 C1 C2 127.0(5) . . ?
N2 C1 C2 114.3(4) . . ?
C7 C2 C3 120.4(5) . . ?
C7 C2 C1 120.2(4) . . ?
C3 C2 C1 119.5(5) . . ?
C4 C3 C2 119.9(6) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.8(5) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 121.4(5) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 120.1(6) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
N1 C7 C2 123.4(4) . . ?
N1 C7 C6 118.1(5) . . ?
C2 C7 C6 118.5(5) . . ?
N1 C8 N2 124.0(4) . . ?
N1 C8 C9 120.8(4) . . ?
N2 C8 C9 115.3(4) . . ?
N3 C9 C8 123.1(4) . . ?
N3 C9 C18 116.8(4) . . ?
C8 C9 C18 120.0(4) . . ?
C11 C10 N2 121.3(4) . . ?
C11 C10 H10 119.3 . . ?
N2 C10 H10 119.3 . . ?
C10 C11 N3 120.2(4) . . ?
C10 C11 C12 123.2(4) . . ?
N3 C11 C12 116.6(4) . . ?
C17 C12 C13 117.7(5) . . ?
C17 C12 C11 119.5(4) . . ?
C13 C12 C11 122.7(5) . . ?
C14 C13 C12 120.8(6) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 120.6(6) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 119.8(5) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 119.9(5) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C12 121.2(5) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
C23 C18 C19 118.9(4) . . ?
C23 C18 C9 122.5(4) . . ?
C19 C18 C9 118.6(4) . . ?
C20 C19 C18 120.0(5) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 120.5(5) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 119.6(5) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 120.2(6) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C18 120.8(5) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?

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
C10 N2 C1 O1 0.8(6) . . . . ?
C8 N2 C1 O1 -177.1(4) . . . . ?
C10 N2 C1 C2 -179.2(4) . . . . ?
C8 N2 C1 C2 2.9(6) . . . . ?
O1 C1 C2 C7 177.0(5) . . . . ?
N2 C1 C2 C7 -3.0(6) . . . . ?
O1 C1 C2 C3 -3.2(8) . . . . ?
N2 C1 C2 C3 176.8(4) . . . . ?
C7 C2 C3 C4 0.1(8) . . . . ?
C1 C2 C3 C4 -179.6(5) . . . . ?
C2 C3 C4 C5 -1.0(8) . . . . ?
C3 C4 C5 C6 1.3(9) . . . . ?
C4 C5 C6 C7 -0.7(8) . . . . ?
C8 N1 C7 C2 0.4(6) . . . . ?
C8 N1 C7 C6 -178.4(4) . . . . ?
C3 C2 C7 N1 -178.3(4) . . . . ?
C1 C2 C7 N1 1.5(7) . . . . ?
C3 C2 C7 C6 0.5(7) . . . . ?
C1 C2 C7 C6 -179.8(4) . . . . ?
C5 C6 C7 N1 178.6(4) . . . . ?
C5 C6 C7 C2 -0.2(7) . . . . ?
C7 N1 C8 N2 -0.5(6) . . . . ?
C7 N1 C8 C9 -179.2(4) . . . . ?
C10 N2 C8 N1 -179.1(4) . . . . ?
C1 N2 C8 N1 -1.3(6) . . . . ?
C10 N2 C8 C9 -0.4(5) . . . . ?
C1 N2 C8 C9 177.5(4) . . . . ?
C11 N3 C9 C8 1.7(6) . . . . ?
C11 N3 C9 C18 177.9(4) . . . . ?
N1 C8 C9 N3 178.3(4) . . . . ?
N2 C8 C9 N3 -0.5(6) . . . . ?
N1 C8 C9 C18 2.2(6) . . . . ?
N2 C8 C9 C18 -176.6(4) . . . . ?
C8 N2 C10 C11 0.0(6) . . . . ?
C1 N2 C10 C11 -177.9(4) . . . . ?
N2 C10 C11 N3 1.2(6) . . . . ?
N2 C10 C11 C12 -179.4(4) . . . . ?
C9 N3 C11 C10 -2.1(6) . . . . ?
C9 N3 C11 C12 178.5(4) . . . . ?
C10 C11 C12 C17 -178.3(4) . . . . ?
N3 C11 C12 C17 1.1(6) . . . . ?
C10 C11 C12 C13 1.8(7) . . . . ?
N3 C11 C12 C13 -178.8(4) . . . . ?
C17 C12 C13 C14 1.1(8) . . . . ?
C11 C12 C13 C14 -179.0(5) . . . . ?
C12 C13 C14 C15 -0.4(9) . . . . ?
C13 C14 C15 C16 -0.5(9) . . . . ?
C14 C15 C16 C17 0.7(8) . . . . ?
C15 C16 C17 C12 0.0(8) . . . . ?
C13 C12 C17 C16 -0.9(7) . . . . ?
C11 C12 C17 C16 179.2(4) . . . . ?
N3 C9 C18 C23 127.5(5) . . . . ?
C8 C9 C18 C23 -56.2(6) . . . . ?
N3 C9 C18 C19 -49.9(6) . . . . ?
C8 C9 C18 C19 126.5(5) . . . . ?
C23 C18 C19 C20 2.7(7) . . . . ?
C9 C18 C19 C20 -179.8(5) . . . . ?
C18 C19 C20 C21 -3.1(8) . . . . ?
C19 C20 C21 C22 0.6(9) . . . . ?
C20 C21 C22 C23 2.2(9) . . . . ?
C21 C22 C23 C18 -2.6(9) . . . . ?
C19 C18 C23 C22 0.1(7) . . . . ?
C9 C18 C23 C22 -177.3(5) . . . . ?

_refine_diff_density_max         0.193
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-4



