# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2105855'
loop_
_audit_author_name
_audit_author_address
'Zhenyu An'
;Lanzhou University
China
;
_audit_update_record             
;
2021-08-27 deposited with the CCDC.	2021-10-19 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            'C17 H12 N2 O2'
_chemical_formula_weight         276.29

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                   19.121(3)
_cell_length_b                   10.8997(15)
_cell_length_c                   12.7763(18)
_cell_angle_alpha                90
_cell_angle_beta                 102.095(2)
_cell_angle_gamma                90
_cell_volume                     2603.6(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3055
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      29.46

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   0.6770
_exptl_transmission_factor_max   0.7462
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_reflns_number            8860
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.163
_diffrn_reflns_theta_max         31.291
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3794
_reflns_number_gt                2591
_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 APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0536P)²+0.9759P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0217(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3794
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1297
_refine_ls_wR_factor_gt          0.1149
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_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 0.80000(7) 0.00669(13) 0.03519(10) 0.0474(3) Uani 1 1 d . . . . .
C2 C 0.75490(8) -0.05520(14) -0.04240(11) 0.0551(4) Uani 1 1 d . . . . .
H2 H 0.7672 -0.1185 -0.0840 0.066 Uiso 1 1 calc R U . . .
C3 C 0.68517(8) -0.00605(13) -0.04899(10) 0.0516(3) Uani 1 1 d . . . . .
C4 C 0.61836(9) -0.03254(17) -0.11456(12) 0.0659(4) Uani 1 1 d . . . . .
H4 H 0.6140 -0.0927 -0.1671 0.079 Uiso 1 1 calc R U . . .
C5 C 0.55951(9) 0.03187(19) -0.09982(14) 0.0731(5) Uani 1 1 d . . . . .
H5 H 0.5152 0.0159 -0.1438 0.088 Uiso 1 1 calc R U . . .
C6 C 0.56503(9) 0.11982(18) -0.02099(14) 0.0699(5) Uani 1 1 d . . . . .
H6 H 0.5240 0.1605 -0.0119 0.084 Uiso 1 1 calc R U . . .
C7 C 0.62950(8) 0.14917(14) 0.04467(12) 0.0572(4) Uani 1 1 d . . . . .
H7 H 0.6326 0.2081 0.0981 0.069 Uiso 1 1 calc R U . . .
C8 C 0.69008(7) 0.08725(12) 0.02814(10) 0.0458(3) Uani 1 1 d . . . . .
C9 C 0.79538(7) 0.17286(11) 0.16430(9) 0.0427(3) Uani 1 1 d . . . . .
C10 C 0.76465(8) 0.27989(12) 0.19217(11) 0.0519(3) Uani 1 1 d . . . . .
H10 H 0.7203 0.3053 0.1533 0.062 Uiso 1 1 calc R U . . .
C11 C 0.79997(9) 0.34880(13) 0.27784(12) 0.0599(4) Uani 1 1 d . . . . .
H11 H 0.7784 0.4194 0.2972 0.072 Uiso 1 1 calc R U . . .
C12 C 0.86626(9) 0.31512(15) 0.33497(12) 0.0604(4) Uani 1 1 d . . . . .
H12 H 0.8892 0.3620 0.3929 0.072 Uiso 1 1 calc R U . . .
C13 C 0.89841(8) 0.21136(15) 0.30575(11) 0.0563(4) Uani 1 1 d . . . . .
H13 H 0.9439 0.1892 0.3426 0.068 Uiso 1 1 calc R U . . .
C14 C 0.86307(7) 0.14001(12) 0.22148(10) 0.0460(3) Uani 1 1 d . . . . .
C15 C 0.90880(8) -0.06817(15) 0.25379(12) 0.0584(4) Uani 1 1 d . . . . .
C16 C 0.90895(10) -0.13150(18) 0.08390(13) 0.0773(5) Uani 1 1 d . . . . .
H16A H 0.8768 -0.1865 0.0371 0.093 Uiso 1 1 calc R U . . .
H16B H 0.9551 -0.1328 0.0637 0.093 Uiso 1 1 calc R U . . .
C17 C 0.87863(8) -0.00153(15) 0.07704(10) 0.0549(4) Uani 1 1 d . . . . .
H17 H 0.9042 0.0515 0.0358 0.066 Uiso 1 1 calc R U . . .
N1 N 0.76202(6) 0.09566(10) 0.07927(8) 0.0436(3) Uani 1 1 d . . . . .
N2 N 0.89515(6) 0.03264(11) 0.18994(9) 0.0503(3) Uani 1 1 d . . . . .
O1 O 0.91587(8) -0.16675(11) 0.19373(10) 0.0816(4) Uani 1 1 d . . . . .
O2 O 0.91513(7) -0.07312(12) 0.34927(9) 0.0758(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 C2 1.3502(19) . ?
C1 N1 1.3988(17) . ?
C1 C17 1.489(2) . ?
C2 C3 1.423(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(2) . ?
C3 C8 1.4054(19) . ?
C4 C5 1.372(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.394(2) . ?
C7 H7 0.9300 . ?
C8 N1 1.3965(17) . ?
C9 C10 1.3859(19) . ?
C9 C14 1.3931(19) . ?
C9 N1 1.4159(16) . ?
C10 C11 1.381(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.376(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.3840(19) . ?
C13 H13 0.9300 . ?
C14 N2 1.4183(17) . ?
C15 O2 1.2016(17) . ?
C15 O1 1.3435(18) . ?
C15 N2 1.361(2) . ?
C16 O1 1.434(2) . ?
C16 C17 1.526(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N2 1.4588(16) . ?
C17 H17 0.9800 . ?

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
C2 C1 N1 109.65(13) . . ?
C2 C1 C17 132.46(13) . . ?
N1 C1 C17 117.87(11) . . ?
C1 C2 C3 107.57(13) . . ?
C1 C2 H2 126.2 . . ?
C3 C2 H2 126.2 . . ?
C4 C3 C8 119.10(15) . . ?
C4 C3 C2 133.03(15) . . ?
C8 C3 C2 107.87(12) . . ?
C5 C4 C3 118.88(16) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.11(16) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 121.93(17) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C8 117.50(15) . . ?
C6 C7 H7 121.2 . . ?
C8 C7 H7 121.2 . . ?
C7 C8 N1 131.71(13) . . ?
C7 C8 C3 121.39(13) . . ?
N1 C8 C3 106.86(12) . . ?
C10 C9 C14 118.61(12) . . ?
C10 C9 N1 123.38(12) . . ?
C14 C9 N1 118.00(11) . . ?
C11 C10 C9 119.87(14) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C12 C11 C10 121.28(14) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 119.38(14) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C12 C13 C14 119.99(14) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 120.80(13) . . ?
C13 C14 N2 120.99(13) . . ?
C9 C14 N2 118.20(11) . . ?
O2 C15 O1 122.90(15) . . ?
O2 C15 N2 127.65(15) . . ?
O1 C15 N2 109.45(13) . . ?
O1 C16 C17 105.13(12) . . ?
O1 C16 H16A 110.7 . . ?
C17 C16 H16A 110.7 . . ?
O1 C16 H16B 110.7 . . ?
C17 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?
N2 C17 C1 109.43(11) . . ?
N2 C17 C16 100.33(12) . . ?
C1 C17 C16 114.78(14) . . ?
N2 C17 H17 110.6 . . ?
C1 C17 H17 110.6 . . ?
C16 C17 H17 110.6 . . ?
C8 N1 C1 108.04(10) . . ?
C8 N1 C9 129.73(11) . . ?
C1 N1 C9 122.17(11) . . ?
C15 N2 C14 122.41(11) . . ?
C15 N2 C17 111.17(12) . . ?
C14 N2 C17 118.34(11) . . ?
C15 O1 C16 110.18(13) . . ?

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
N1 C1 C2 C3 -0.41(16) . . . . ?
C17 C1 C2 C3 -178.78(14) . . . . ?
C1 C2 C3 C4 179.13(15) . . . . ?
C1 C2 C3 C8 -0.37(16) . . . . ?
C8 C3 C4 C5 -1.3(2) . . . . ?
C2 C3 C4 C5 179.20(16) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C4 C5 C6 C7 1.5(3) . . . . ?
C5 C6 C7 C8 0.6(2) . . . . ?
C6 C7 C8 N1 179.58(14) . . . . ?
C6 C7 C8 C3 -3.1(2) . . . . ?
C4 C3 C8 C7 3.5(2) . . . . ?
C2 C3 C8 C7 -176.88(12) . . . . ?
C4 C3 C8 N1 -178.59(12) . . . . ?
C2 C3 C8 N1 1.00(14) . . . . ?
C14 C9 C10 C11 -2.55(19) . . . . ?
N1 C9 C10 C11 178.51(12) . . . . ?
C9 C10 C11 C12 1.7(2) . . . . ?
C10 C11 C12 C13 0.6(2) . . . . ?
C11 C12 C13 C14 -1.9(2) . . . . ?
C12 C13 C14 C9 1.0(2) . . . . ?
C12 C13 C14 N2 -179.99(12) . . . . ?
C10 C9 C14 C13 1.25(19) . . . . ?
N1 C9 C14 C13 -179.75(12) . . . . ?
C10 C9 C14 N2 -177.80(11) . . . . ?
N1 C9 C14 N2 1.19(17) . . . . ?
C2 C1 C17 N2 -149.82(15) . . . . ?
N1 C1 C17 N2 31.92(18) . . . . ?
C2 C1 C17 C16 -38.0(2) . . . . ?
N1 C1 C17 C16 143.77(13) . . . . ?
O1 C16 C17 N2 18.16(17) . . . . ?
O1 C16 C17 C1 -99.01(15) . . . . ?
C7 C8 N1 C1 176.33(14) . . . . ?
C3 C8 N1 C1 -1.24(13) . . . . ?
C7 C8 N1 C9 -0.9(2) . . . . ?
C3 C8 N1 C9 -178.49(12) . . . . ?
C2 C1 N1 C8 1.04(15) . . . . ?
C17 C1 N1 C8 179.68(12) . . . . ?
C2 C1 N1 C9 178.54(11) . . . . ?
C17 C1 N1 C9 -2.82(18) . . . . ?
C10 C9 N1 C8 -19.53(19) . . . . ?
C14 C9 N1 C8 161.53(12) . . . . ?
C10 C9 N1 C1 163.57(12) . . . . ?
C14 C9 N1 C1 -15.38(17) . . . . ?
O2 C15 N2 C14 -21.7(2) . . . . ?
O1 C15 N2 C14 159.35(13) . . . . ?
O2 C15 N2 C17 -169.78(16) . . . . ?
O1 C15 N2 C17 11.27(17) . . . . ?
C13 C14 N2 C15 66.41(18) . . . . ?
C9 C14 N2 C15 -114.54(15) . . . . ?
C13 C14 N2 C17 -147.65(13) . . . . ?
C9 C14 N2 C17 31.40(17) . . . . ?
C1 C17 N2 C15 102.88(15) . . . . ?
C16 C17 N2 C15 -18.19(16) . . . . ?
C1 C17 N2 C14 -46.65(17) . . . . ?
C16 C17 N2 C14 -167.72(13) . . . . ?
O2 C15 O1 C16 -177.16(16) . . . . ?
N2 C15 O1 C16 1.85(19) . . . . ?
C17 C16 O1 C15 -13.24(19) . . . . ?

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.032

