# 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_zhaoyl190508_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1994945'
loop_
_audit_author_name
_audit_author_address
'Zhan-Gang Han'
;Professor
China
;
_audit_update_record             
;
2020-04-05 deposited with the CCDC.	2020-09-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H14 N2 O2'
_chemical_formula_weight         302.32

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           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                   16.6278(15)
_cell_length_b                   8.6481(8)
_cell_length_c                   20.7233(19)
_cell_angle_alpha                90
_cell_angle_beta                 100.593(5)
_cell_angle_gamma                90
_cell_volume                     2929.2(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    6904
_cell_measurement_theta_min      5.41
_cell_measurement_theta_max      68.41

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.730
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11455
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         5.413
_diffrn_reflns_theta_max         69.650
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2698
_reflns_number_gt                2162
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0419P)²+2.8218P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00172(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2698
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1139
_refine_ls_wR_factor_gt          0.1053
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
C1 C 0.08990(10) 0.1178(2) 0.40249(8) 0.0363(4) Uani 1 1 d . . . . .
C2 C 0.00856(10) 0.1063(2) 0.40986(8) 0.0384(4) Uani 1 1 d . . . . .
H2 H -0.0277 0.0484 0.3798 0.046 Uiso 1 1 calc R U . . .
C3 C -0.01957(10) 0.1798(2) 0.46118(8) 0.0363(4) Uani 1 1 d . . . . .
C4 C 0.03675(10) 0.2659(2) 0.50554(8) 0.0358(4) Uani 1 1 d . . . . .
C5 C 0.11885(10) 0.2639(2) 0.49441(8) 0.0361(4) Uani 1 1 d . . . . .
C6 C 0.03749(11) 0.3632(2) 0.56269(8) 0.0381(4) Uani 1 1 d . . . . .
C7 C 0.11944(11) 0.4112(2) 0.58319(9) 0.0411(4) Uani 1 1 d . . . . .
C8 C 0.14253(13) 0.5107(2) 0.63582(9) 0.0508(5) Uani 1 1 d . . . . .
H8 H 0.1965 0.5435 0.6479 0.061 Uiso 1 1 calc R U . . .
C9 C 0.08333(14) 0.5594(2) 0.66946(10) 0.0557(6) Uani 1 1 d . . . . .
H9 H 0.0978 0.6239 0.7056 0.067 Uiso 1 1 calc R U . . .
C10 C 0.00224(14) 0.5141(2) 0.65058(10) 0.0535(5) Uani 1 1 d . . . . .
H10 H -0.0366 0.5489 0.6743 0.064 Uiso 1 1 calc R U . . .
C11 C -0.02142(12) 0.4188(2) 0.59742(9) 0.0450(5) Uani 1 1 d . . . . .
H11 H -0.0761 0.3913 0.5846 0.054 Uiso 1 1 calc R U . . .
C12 C 0.11634(10) 0.0501(2) 0.34379(9) 0.0388(4) Uani 1 1 d . . . . .
C13 C 0.16306(12) 0.1355(2) 0.30774(9) 0.0478(5) Uani 1 1 d . . . . .
H13 H 0.1807 0.2340 0.3219 0.057 Uiso 1 1 calc R U . . .
C14 C 0.18381(14) 0.0765(3) 0.25116(10) 0.0580(6) Uani 1 1 d . . . . .
H14 H 0.2143 0.1360 0.2270 0.070 Uiso 1 1 calc R U . . .
C15 C 0.15957(13) -0.0698(3) 0.23043(10) 0.0585(6) Uani 1 1 d . . . . .
H15 H 0.1739 -0.1100 0.1925 0.070 Uiso 1 1 calc R U . . .
C16 C 0.11420(15) -0.1563(3) 0.26591(11) 0.0629(6) Uani 1 1 d . . . . .
H16 H 0.0983 -0.2560 0.2523 0.075 Uiso 1 1 calc R U . . .
C17 C 0.09187(13) -0.0963(2) 0.32199(10) 0.0550(5) Uani 1 1 d . . . . .
H17 H 0.0600 -0.1553 0.3452 0.066 Uiso 1 1 calc R U . . .
C18 C -0.10748(11) 0.1682(2) 0.46677(9) 0.0421(4) Uani 1 1 d . . . . .
C19 C -0.23774(12) 0.0756(3) 0.41980(12) 0.0642(6) Uani 1 1 d . . . . .
H19A H -0.2454 0.0345 0.4613 0.096 Uiso 1 1 calc R U . . .
H19B H -0.2630 0.0082 0.3851 0.096 Uiso 1 1 calc R U . . .
H19C H -0.2622 0.1763 0.4136 0.096 Uiso 1 1 calc R U . . .
H1A H 0.2232(14) 0.351(2) 0.5479(10) 0.060(6) Uiso 1 1 d . . . . .
N1 N 0.14672(8) 0.19506(17) 0.44522(7) 0.0387(4) Uani 1 1 d . . . . .
N2 N 0.16761(10) 0.34909(19) 0.54167(8) 0.0440(4) Uani 1 1 d . . . . .
O1 O -0.13642(9) 0.2230(3) 0.50982(9) 0.0939(7) Uani 1 1 d . . . . .
O2 O -0.15137(8) 0.08729(18) 0.41895(7) 0.0575(4) Uani 1 1 d . . . . .


_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
C1 N1 1.348(2) . ?
C1 C2 1.392(2) . ?
C1 C12 1.487(2) . ?
C2 C3 1.391(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.400(2) . ?
C3 C18 1.491(2) . ?
C4 C5 1.426(2) . ?
C4 C6 1.451(2) . ?
C5 N1 1.335(2) . ?
C5 N2 1.366(2) . ?
C6 C11 1.403(2) . ?
C6 C7 1.413(3) . ?
C7 C8 1.387(3) . ?
C7 N2 1.387(2) . ?
C8 C9 1.373(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C17 1.381(3) . ?
C12 C13 1.386(3) . ?
C13 C14 1.379(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.369(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.384(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O1 1.187(2) . ?
C18 O2 1.318(2) . ?
C19 O2 1.443(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N2 H1A 0.91(2) . ?

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
N1 C1 C2 122.76(16) . . ?
N1 C1 C12 117.11(15) . . ?
C2 C1 C12 120.06(16) . . ?
C3 C2 C1 121.41(16) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 117.80(15) . . ?
C2 C3 C18 120.06(16) . . ?
C4 C3 C18 122.13(16) . . ?
C3 C4 C5 115.61(15) . . ?
C3 C4 C6 138.47(16) . . ?
C5 C4 C6 105.91(15) . . ?
N1 C5 N2 122.97(15) . . ?
N1 C5 C4 127.29(16) . . ?
N2 C5 C4 109.72(15) . . ?
C11 C6 C7 118.08(17) . . ?
C11 C6 C4 135.70(17) . . ?
C7 C6 C4 106.19(15) . . ?
C8 C7 N2 128.32(18) . . ?
C8 C7 C6 122.07(17) . . ?
N2 C7 C6 109.55(16) . . ?
C9 C8 C7 117.96(19) . . ?
C9 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
C8 C9 C10 121.35(19) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C11 C10 C9 120.97(19) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C6 119.54(19) . . ?
C10 C11 H11 120.2 . . ?
C6 C11 H11 120.2 . . ?
C17 C12 C13 118.25(17) . . ?
C17 C12 C1 120.99(17) . . ?
C13 C12 C1 120.69(17) . . ?
C14 C13 C12 120.9(2) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 119.7(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C12 C17 C16 120.7(2) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
O1 C18 O2 122.12(17) . . ?
O1 C18 C3 124.76(18) . . ?
O2 C18 C3 113.11(15) . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C5 N1 C1 115.03(14) . . ?
C5 N2 C7 108.60(15) . . ?
C5 N2 H1A 124.3(14) . . ?
C7 N2 H1A 126.4(14) . . ?
C18 O2 C19 116.27(15) . . ?

_refine_diff_density_max         0.307
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.038



