# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_ddz20083_0m
_database_code_depnum_ccdc_archive 'CCDC 2101003'
loop_
_audit_author_name
_audit_author_address
'Yunfeng Liao'
;College of Materials and Chemical Engineering, Hunan Institute of Engineering
China
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2021-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 N3 O2'
_chemical_formula_weight         317.34

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                   22.630(7)
_cell_length_b                   3.8102(11)
_cell_length_c                   18.998(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.852(8)
_cell_angle_gamma                90
_cell_volume                     1613.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2378
_cell_measurement_theta_min      4.352
_cell_measurement_theta_max      54.058

_exptl_crystal_description       prismatic
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6177
_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            9644
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.591
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             1428
_reflns_number_gt                839
_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)+(0.2000P)²] 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       0.026(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1428
_refine_ls_number_parameters     157
_refine_ls_number_restraints     73
_refine_ls_R_factor_all          0.1616
_refine_ls_R_factor_gt           0.1168
_refine_ls_wR_factor_ref         0.3829
_refine_ls_wR_factor_gt          0.3369
_refine_ls_goodness_of_fit_ref   1.389
_refine_ls_restrained_S_all      1.381
_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 0.4743(3) 0.3312(17) 0.3687(3) 0.0631(18) Uani 0.5 1 d D . P . .
N2 N 0.5786(2) 0.1795(12) 0.3954(3) 0.0747(15) Uani 0.5 1 d . . P . .
N1 N 0.57657(17) -0.0741(10) 0.2567(2) 0.0722(14) Uani 1 1 d . . . . .
C1 C 0.6298(2) 0.0397(12) 0.3766(3) 0.0672(14) Uani 1 1 d . . . . .
C2 C 0.6840(2) 0.0240(13) 0.4257(3) 0.0736(16) Uani 1 1 d . . . . .
H2 H 0.6858 0.1076 0.4720 0.088 Uiso 1 1 calc R U . . .
C3 C 0.7342(2) -0.1146(13) 0.4049(3) 0.0743(16) Uani 1 1 d . . . . .
H3 H 0.7698 -0.1290 0.4376 0.089 Uiso 1 1 calc R U . . .
C4 C 0.7324(2) -0.2350(13) 0.3349(3) 0.0730(15) Uani 1 1 d . . . . .
H4 H 0.7671 -0.3225 0.3212 0.088 Uiso 1 1 calc R U . . .
C5 C 0.6805(2) -0.2253(13) 0.2867(3) 0.0669(15) Uani 1 1 d . . . . .
H5 H 0.6798 -0.3128 0.2409 0.080 Uiso 1 1 calc R U . . .
C6 C 0.6278(2) -0.0834(11) 0.3058(3) 0.0620(14) Uani 1 1 d . . . . .
C7 C 0.5279(2) 0.0544(12) 0.2769(3) 0.0662(15) Uani 1 1 d . . . . .
C8 C 0.5286(2) 0.1911(14) 0.3468(3) 0.0745(16) Uani 1 1 d . . . . .
C9 C 0.5786(2) 0.1795(12) 0.3954(3) 0.0747(15) Uani 0.5 1 d . . P . .
H9 H 0.5788 0.2646 0.4413 0.090 Uiso 0.5 1 calc R U P . .
O2 O 0.3978(4) 0.921(2) 0.3798(4) 0.0355(15) Uani 0.25 1 d D U P A 1
H2A H 0.4149 1.0924 0.3999 0.053 Uiso 0.25 1 calc R U P A 1
C10 C 0.4695(5) 0.521(3) 0.4332(6) 0.0379(15) Uani 0.3 1 d D U P A 1
H10A H 0.4809 0.3721 0.4748 0.046 Uiso 0.3 1 calc R U P A 1
H10B H 0.4953 0.7256 0.4380 0.046 Uiso 0.3 1 calc R U P A 1
C11 C 0.4083(4) 0.622(3) 0.4262(5) 0.0374(15) Uani 0.4 1 d D U P A 1
H11A H 0.3988 0.6802 0.4727 0.045 Uiso 0.4 1 calc R U P A 1
H11B H 0.3826 0.4293 0.4065 0.045 Uiso 0.4 1 calc R U P A 1
O2' O 0.3957(5) 0.711(3) 0.4040(5) 0.0380(16) Uani 0.25 1 d D U P A 2
H2' H 0.4259 0.8240 0.4005 0.057 Uiso 0.25 1 calc R U P A 2
C10' C 0.4741(8) 0.398(5) 0.4430(7) 0.0380(16) Uani 0.2 1 d D U P A 2
H10C H 0.4975 0.6062 0.4586 0.046 Uiso 0.2 1 calc R U P A 2
H10D H 0.4908 0.2007 0.4719 0.046 Uiso 0.2 1 calc R U P A 2
C11' C 0.4100(11) 0.452(8) 0.4490(16) 0.0379(15) Uani 0.1 1 d D U P A 2
H11C H 0.3862 0.2437 0.4346 0.045 Uiso 0.1 1 calc R U P A 2
H11D H 0.4055 0.5170 0.4971 0.045 Uiso 0.1 1 calc R U P A 2


_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 C10' 1.435(14) . ?
O1 C10 1.442(11) . ?
O1 C8 1.462(8) . ?
N2 C8 1.333(7) . ?
N2 C1 1.378(7) . ?
N1 C7 1.322(6) . ?
N1 C6 1.359(6) . ?
C1 C2 1.410(7) . ?
C1 C6 1.417(7) . ?
C2 C3 1.370(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.401(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.360(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.413(6) . ?
C5 H5 0.9300 . ?
C7 C8 1.424(8) . ?
C7 C7 1.483(9) 2_655 ?
O2 C11 1.434(10) . ?
O2 H2A 0.8200 . ?
C10 C11 1.423(13) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
O2' C11' 1.310(18) . ?
O2' H2' 0.8200 . ?
C10' C11' 1.489(18) . ?
C10' H10C 0.9700 . ?
C10' H10D 0.9700 . ?
C11' H11C 0.9700 . ?
C11' H11D 0.9700 . ?

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
C10' O1 C8 119.3(7) . . ?
C10 O1 C8 127.8(6) . . ?
C8 N2 C1 119.0(5) . . ?
C7 N1 C6 117.8(5) . . ?
N2 C1 C2 121.4(5) . . ?
N2 C1 C6 118.9(5) . . ?
C2 C1 C6 119.7(5) . . ?
C3 C2 C1 119.7(5) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 120.6(5) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 120.7(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.5(5) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
N1 C6 C5 119.5(5) . . ?
N1 C6 C1 121.8(4) . . ?
C5 C6 C1 118.7(4) . . ?
N1 C7 C8 122.0(5) . . ?
N1 C7 C7 116.9(6) . 2_655 ?
C8 C7 C7 121.1(5) . 2_655 ?
N2 C8 C7 120.4(5) . . ?
N2 C8 O1 118.0(5) . . ?
C7 C8 O1 121.5(5) . . ?
C11 O2 H2A 109.5 . . ?
C11 C10 O1 105.7(9) . . ?
C11 C10 H10A 110.6 . . ?
O1 C10 H10A 110.6 . . ?
C11 C10 H10B 110.6 . . ?
O1 C10 H10B 110.6 . . ?
H10A C10 H10B 108.7 . . ?
C10 C11 O2 109.1(9) . . ?
C10 C11 H11A 109.9 . . ?
O2 C11 H11A 109.9 . . ?
C10 C11 H11B 109.9 . . ?
O2 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C11' O2' H2' 109.5 . . ?
O1 C10' C11' 105.5(16) . . ?
O1 C10' H10C 110.6 . . ?
C11' C10' H10C 110.7 . . ?
O1 C10' H10D 110.6 . . ?
C11' C10' H10D 110.6 . . ?
H10C C10' H10D 108.8 . . ?
O2' C11' C10' 100.8(15) . . ?
O2' C11' H11C 111.6 . . ?
C10' C11' H11C 111.6 . . ?
O2' C11' H11D 111.6 . . ?
C10' C11' H11D 111.6 . . ?
H11C C11' H11D 109.4 . . ?

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
C8 N2 C1 C2 179.4(4) . . . . ?
C8 N2 C1 C6 0.8(7) . . . . ?
N2 C1 C2 C3 -179.6(5) . . . . ?
C6 C1 C2 C3 -0.9(7) . . . . ?
C1 C2 C3 C4 1.2(8) . . . . ?
C2 C3 C4 C5 -1.8(8) . . . . ?
C3 C4 C5 C6 2.0(7) . . . . ?
C7 N1 C6 C5 178.7(4) . . . . ?
C7 N1 C6 C1 0.0(6) . . . . ?
C4 C5 C6 N1 179.5(4) . . . . ?
C4 C5 C6 C1 -1.7(7) . . . . ?
N2 C1 C6 N1 -1.5(7) . . . . ?
C2 C1 C6 N1 179.9(4) . . . . ?
N2 C1 C6 C5 179.8(4) . . . . ?
C2 C1 C6 C5 1.1(7) . . . . ?
C6 N1 C7 C8 2.1(7) . . . . ?
C6 N1 C7 C7 -178.6(3) . . . 2_655 ?
C1 N2 C8 C7 1.3(7) . . . . ?
C1 N2 C8 O1 178.2(5) . . . . ?
N1 C7 C8 N2 -2.8(8) . . . . ?
C7 C7 C8 N2 177.9(4) 2_655 . . . ?
N1 C7 C8 O1 -179.7(5) . . . . ?
C7 C7 C8 O1 1.1(7) 2_655 . . . ?
C10' O1 C8 N2 -9.7(12) . . . . ?
C10 O1 C8 N2 12.4(11) . . . . ?
C10' O1 C8 C7 167.2(10) . . . . ?
C10 O1 C8 C7 -170.6(7) . . . . ?
C10' O1 C10 C11 -113(3) . . . . ?
C8 O1 C10 C11 175.5(7) . . . . ?
O1 C10 C11 O2 -78.3(11) . . . . ?
C10 O1 C10' C11' 73(3) . . . . ?
C8 O1 C10' C11' -166.5(13) . . . . ?
O1 C10' C11' O2' -57(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11A N2 0.97 2.53 3.435(11) 156.0 5_666
O2 H2A O1 0.82 1.81 2.369(11) 124.6 1_565
C11 H11A N2 0.97 2.53 3.435(11) 156.0 5_666
O2 H2A O1 0.82 1.81 2.369(11) 124.6 1_565

_refine_diff_density_max         0.685
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.097

_shelxl_version_number           2013-4

