# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_T
_database_code_depnum_ccdc_archive 'CCDC 2104863'
loop_
_audit_author_name
_audit_author_address
'Zhaoliang Xu'
;Huaibei Normal University
China
;
_audit_update_record             
;
2021-08-20 deposited with the CCDC.	2021-10-28 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         'C17 H14 N2 O2'
_chemical_formula_sum            'C17 H14 N2 O2'
_chemical_formula_weight         278.30

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.631(2)
_cell_length_b                   14.557(3)
_cell_length_c                   15.796(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2674.5(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    15946
_cell_measurement_theta_min      2.579
_cell_measurement_theta_max      28.580

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   'SADABS; Bruker, 2008'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15946
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.579
_diffrn_reflns_theta_max         28.580
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3352
_reflns_number_gt                1878
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0466P)²+0.1083P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0038(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3352
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1143
_refine_ls_wR_factor_gt          0.0937
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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 0.44495(9) 0.62492(7) 0.10271(7) 0.0540(3) Uani 1 1 d . . . . .
O2 O 0.33691(10) 0.31316(7) 0.03632(8) 0.0642(4) Uani 1 1 d . . . . .
N1 N 0.40607(10) 0.45435(8) 0.07320(8) 0.0422(3) Uani 1 1 d . . . . .
H1A H 0.3942 0.5124 0.0634 0.051 Uiso 1 1 calc R U . . .
N2 N 0.23848(11) 0.53688(9) -0.00689(8) 0.0529(4) Uani 1 1 d . . . . .
C1 C 0.49783(13) 0.43525(10) 0.12777(9) 0.0404(4) Uani 1 1 d . . . . .
C2 C 0.53332(14) 0.34712(11) 0.14141(10) 0.0510(4) Uani 1 1 d . . . . .
H2A H 0.4963 0.2986 0.1132 0.061 Uiso 1 1 calc R U . . .
C3 C 0.62353(16) 0.32809(13) 0.19647(11) 0.0591(5) Uani 1 1 d . . . . .
H3A H 0.6477 0.2670 0.2041 0.071 Uiso 1 1 calc R U . . .
C4 C 0.67677(15) 0.39630(12) 0.23914(11) 0.0578(5) Uani 1 1 d . . . . .
H4A H 0.7371 0.3821 0.2765 0.069 Uiso 1 1 calc R U . . .
C5 C 0.64329(13) 0.48798(11) 0.22845(10) 0.0465(4) Uani 1 1 d . . . . .
C6 C 0.55402(12) 0.50989(10) 0.17041(9) 0.0391(4) Uani 1 1 d . . . . .
C7 C 0.52802(13) 0.60471(10) 0.16047(9) 0.0422(4) Uani 1 1 d . . . . .
C8 C 0.58304(14) 0.67072(11) 0.20611(10) 0.0512(4) Uani 1 1 d . . . . .
H8A H 0.5644 0.7329 0.1979 0.061 Uiso 1 1 calc R U . . .
C9 C 0.66667(14) 0.64652(13) 0.26475(11) 0.0580(5) Uani 1 1 d . . . . .
H9A H 0.7023 0.6923 0.2976 0.070 Uiso 1 1 calc R U . . .
C10 C 0.69700(15) 0.55823(13) 0.27488(10) 0.0567(5) Uani 1 1 d . . . . .
H10A H 0.7552 0.5431 0.3137 0.068 Uiso 1 1 calc R U . . .
C11 C 0.33366(13) 0.39674(11) 0.03375(10) 0.0440(4) Uani 1 1 d . . . . .
C12 C 0.24263(13) 0.44612(11) -0.01529(9) 0.0433(4) Uani 1 1 d . . . . .
C13 C 0.16824(14) 0.39798(12) -0.06575(11) 0.0555(4) Uani 1 1 d . . . . .
H13A H 0.1737 0.3337 -0.0704 0.067 Uiso 1 1 calc R U . . .
C14 C 0.08562(16) 0.44570(15) -0.10935(12) 0.0687(5) Uani 1 1 d . . . . .
H14A H 0.0333 0.4146 -0.1445 0.082 Uiso 1 1 calc R U . . .
C15 C 0.08033(16) 0.53843(14) -0.10113(12) 0.0706(6) Uani 1 1 d . . . . .
H15A H 0.0244 0.5725 -0.1304 0.085 Uiso 1 1 calc R U . . .
C16 C 0.15772(16) 0.58122(13) -0.04959(12) 0.0663(5) Uani 1 1 d . . . . .
H16A H 0.1535 0.6454 -0.0441 0.080 Uiso 1 1 calc R U . . .
C17 C 0.41782(15) 0.71724(11) 0.08355(11) 0.0580(5) Uani 1 1 d . . . . .
H17A H 0.3572 0.7189 0.0414 0.087 Uiso 1 1 calc R U . . .
H17B H 0.3921 0.7482 0.1345 0.087 Uiso 1 1 calc R U . . .
H17C H 0.4856 0.7479 0.0616 0.087 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 C7 1.3611(17) . ?
O1 C17 1.4131(18) . ?
O2 C11 1.2178(17) . ?
N1 C11 1.3421(18) . ?
N1 C1 1.3998(18) . ?
N1 H1A 0.8700 . ?
N2 C16 1.324(2) . ?
N2 C12 1.3288(18) . ?
C1 C2 1.365(2) . ?
C1 C6 1.436(2) . ?
C2 C3 1.391(2) . ?
C2 H2A 0.9400 . ?
C3 C4 1.350(2) . ?
C3 H3A 0.9400 . ?
C4 C5 1.400(2) . ?
C4 H4A 0.9400 . ?
C5 C10 1.405(2) . ?
C5 C6 1.421(2) . ?
C6 C7 1.422(2) . ?
C7 C8 1.361(2) . ?
C8 C9 1.389(2) . ?
C8 H8A 0.9400 . ?
C9 C10 1.342(2) . ?
C9 H9A 0.9400 . ?
C10 H10A 0.9400 . ?
C11 C12 1.496(2) . ?
C12 C13 1.369(2) . ?
C13 C14 1.371(2) . ?
C13 H13A 0.9400 . ?
C14 C15 1.357(3) . ?
C14 H14A 0.9400 . ?
C15 C16 1.364(2) . ?
C15 H15A 0.9400 . ?
C16 H16A 0.9400 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 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
C7 O1 C17 120.51(12) . . ?
C11 N1 C1 129.81(13) . . ?
C11 N1 H1A 115.1 . . ?
C1 N1 H1A 115.1 . . ?
C16 N2 C12 117.35(14) . . ?
C2 C1 N1 120.97(14) . . ?
C2 C1 C6 119.97(14) . . ?
N1 C1 C6 119.05(13) . . ?
C1 C2 C3 120.94(16) . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 H2A 119.5 . . ?
C4 C3 C2 120.77(16) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C3 C4 C5 120.87(16) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C4 C5 C10 120.47(16) . . ?
C4 C5 C6 119.65(15) . . ?
C10 C5 C6 119.88(15) . . ?
C5 C6 C7 116.39(13) . . ?
C5 C6 C1 117.73(14) . . ?
C7 C6 C1 125.88(14) . . ?
O1 C7 C8 122.43(15) . . ?
O1 C7 C6 115.78(13) . . ?
C8 C7 C6 121.79(15) . . ?
C7 C8 C9 120.24(16) . . ?
C7 C8 H8A 119.9 . . ?
C9 C8 H8A 119.9 . . ?
C10 C9 C8 120.43(16) . . ?
C10 C9 H9A 119.8 . . ?
C8 C9 H9A 119.8 . . ?
C9 C10 C5 121.18(16) . . ?
C9 C10 H10A 119.4 . . ?
C5 C10 H10A 119.4 . . ?
O2 C11 N1 126.11(15) . . ?
O2 C11 C12 121.28(14) . . ?
N1 C11 C12 112.60(13) . . ?
N2 C12 C13 122.96(15) . . ?
N2 C12 C11 116.86(13) . . ?
C13 C12 C11 120.18(15) . . ?
C12 C13 C14 118.42(17) . . ?
C12 C13 H13A 120.8 . . ?
C14 C13 H13A 120.8 . . ?
C15 C14 C13 119.17(17) . . ?
C15 C14 H14A 120.4 . . ?
C13 C14 H14A 120.4 . . ?
C14 C15 C16 118.76(18) . . ?
C14 C15 H15A 120.6 . . ?
C16 C15 H15A 120.6 . . ?
N2 C16 C15 123.33(18) . . ?
N2 C16 H16A 118.3 . . ?
C15 C16 H16A 118.3 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.034



