# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1953774'
loop_
_audit_author_name
_audit_author_address
'Hadi Rudbari' 'Isfahan University'
_audit_update_record             
;
2019-09-16 deposited with the CCDC.	2021-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N2 O2'
_chemical_formula_weight         316.35

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   9.7420(19)
_cell_length_b                   16.082(3)
_cell_length_c                   11.405(2)
_cell_angle_alpha                90
_cell_angle_beta                 115.05(3)
_cell_angle_gamma                90
_cell_volume                     1618.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3569
_cell_measurement_theta_min      5.04
_cell_measurement_theta_max      48.33

_exptl_crystal_description       flat
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Stoe IPDS-II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10238
_diffrn_reflns_av_unetI/netI     0.1456
_diffrn_reflns_av_R_equivalents  0.1897
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.533
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_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             2860
_reflns_number_gt                1394
_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       'X-AREA (Stoe & Cie, 2005)'
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2005)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2005)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1997)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0728P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2860
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1269
_refine_ls_R_factor_gt           0.0721
_refine_ls_wR_factor_ref         0.1852
_refine_ls_wR_factor_gt          0.1622
_refine_ls_goodness_of_fit_ref   0.827
_refine_ls_restrained_S_all      0.827
_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 -0.2149(2) 0.05199(18) 0.8554(2) 0.0642(7) Uani 1 1 d . . . . .
H1 H -0.301027 0.039467 0.844630 0.096 Uiso 1 1 calc R U . . .
O2 O 0.4965(2) 0.02753(18) 0.8316(3) 0.0632(7) Uani 1 1 d D . . . .
N1 N 0.2882(3) 0.11315(17) 0.8407(3) 0.0524(7) Uani 1 1 d . . . . .
C8 C 0.2161(3) 0.0478(2) 0.8506(3) 0.0436(8) Uani 1 1 d . . . . .
C7 C 0.0698(3) 0.0571(2) 0.8676(3) 0.0442(8) Uani 1 1 d . . . . .
H7 H 0.056023 0.007226 0.910744 0.053 Uiso 1 1 calc R U . . .
C1 C -0.0671(3) 0.06612(19) 0.7376(3) 0.0428(8) Uani 1 1 d . . . . .
C9 C 0.2790(3) -0.0338(2) 0.8456(3) 0.0482(8) Uani 1 1 d . . . . .
N2 N 0.0931(3) 0.12841(18) 0.9542(3) 0.0532(8) Uani 1 1 d . . . . .
C3 C -0.3402(4) 0.0742(2) 0.6241(3) 0.0578(9) Uani 1 1 d . . . . .
H3 H -0.435345 0.072868 0.624672 0.069 Uiso 1 1 calc R U . . .
C2 C -0.2119(3) 0.0641(2) 0.7387(3) 0.0477(8) Uani 1 1 d . . . . .
C6 C -0.0589(3) 0.0783(2) 0.6204(3) 0.0514(9) Uani 1 1 d . . . . .
H6 H 0.035743 0.079744 0.618819 0.062 Uiso 1 1 calc R U . . .
C15 C 0.2398(3) 0.1923(2) 0.8572(3) 0.0521(8) Uani 1 1 d . . . . .
C13 C 0.4839(4) -0.1183(3) 0.8441(3) 0.0647(10) Uani 1 1 d . . . . .
H13 H 0.579494 -0.122422 0.844795 0.078 Uiso 1 1 calc R U . . .
C14 C 0.4215(4) -0.0409(2) 0.8393(3) 0.0528(9) Uani 1 1 d . . . . .
C10 C 0.2028(4) -0.1077(2) 0.8481(3) 0.0579(9) Uani 1 1 d . . . . .
H10 H 0.107737 -0.104622 0.848615 0.069 Uiso 1 1 calc R U . . .
C20 C 0.1424(3) 0.2012(2) 0.9187(3) 0.0499(8) Uani 1 1 d . . . . .
C4 C -0.3283(4) 0.0860(2) 0.5100(4) 0.0640(10) Uani 1 1 d . . . . .
H4 H -0.415603 0.092554 0.433659 0.077 Uiso 1 1 calc R U . . .
C5 C -0.1861(4) 0.0884(3) 0.5068(3) 0.0630(10) Uani 1 1 d . . . . .
H5 H -0.178179 0.096605 0.429153 0.076 Uiso 1 1 calc R U . . .
C16 C 0.2974(4) 0.2628(3) 0.8233(4) 0.0731(12) Uani 1 1 d . . . . .
H16 H 0.361046 0.257315 0.781814 0.088 Uiso 1 1 calc R U . . .
C12 C 0.4087(5) -0.1894(3) 0.8479(4) 0.0744(11) Uani 1 1 d . . . . .
H12 H 0.452198 -0.241041 0.849304 0.089 Uiso 1 1 calc R U . . .
C19 C 0.1122(4) 0.2793(3) 0.9509(4) 0.0719(11) Uani 1 1 d . . . . .
H19 H 0.052764 0.285473 0.996181 0.086 Uiso 1 1 calc R U . . .
C11 C 0.2660(5) -0.1842(2) 0.8498(4) 0.0746(11) Uani 1 1 d . . . . .
H11 H 0.214401 -0.232357 0.852096 0.090 Uiso 1 1 calc R U . . .
C18 C 0.1699(5) 0.3484(3) 0.9162(4) 0.0830(14) Uani 1 1 d . . . . .
H18 H 0.147779 0.401114 0.936867 0.100 Uiso 1 1 calc R U . . .
C17 C 0.2607(5) 0.3400(3) 0.8507(5) 0.0849(14) Uani 1 1 d . . . . .
H17 H 0.296702 0.387004 0.825383 0.102 Uiso 1 1 calc R U . . .
H2A H 0.014(5) 0.143(2) 0.983(4) 0.085(13) Uiso 1 1 d . . . . .
H2 H 0.454(4) 0.0725(13) 0.826(4) 0.087(15) Uiso 1 1 d 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
O1 C2 1.358(4) . ?
O1 H1 0.8200 . ?
O2 C14 1.345(4) . ?
O2 H2 0.821(2) . ?
N1 C8 1.295(4) . ?
N1 C15 1.397(4) . ?
C8 C9 1.460(4) . ?
C8 C7 1.525(4) . ?
C7 N2 1.467(4) . ?
C7 C1 1.524(4) . ?
C7 H7 0.9800 . ?
C1 C6 1.387(4) . ?
C1 C2 1.416(4) . ?
C9 C10 1.408(5) . ?
C9 C14 1.425(4) . ?
N2 C20 1.388(4) . ?
N2 H2A 0.99(4) . ?
C3 C4 1.368(5) . ?
C3 C2 1.383(5) . ?
C3 H3 0.9300 . ?
C6 C5 1.372(5) . ?
C6 H6 0.9300 . ?
C15 C16 1.391(5) . ?
C15 C20 1.406(5) . ?
C13 C12 1.368(6) . ?
C13 C14 1.376(5) . ?
C13 H13 0.9300 . ?
C10 C11 1.372(5) . ?
C10 H10 0.9300 . ?
C20 C19 1.375(5) . ?
C4 C5 1.402(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C16 C17 1.364(6) . ?
C16 H16 0.9300 . ?
C12 C11 1.402(6) . ?
C12 H12 0.9300 . ?
C19 C18 1.377(6) . ?
C19 H19 0.9300 . ?
C11 H11 0.9300 . ?
C18 C17 1.384(6) . ?
C18 H18 0.9300 . ?
C17 H17 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
C2 O1 H1 109.5 . . ?
C14 O2 H2 117(3) . . ?
C8 N1 C15 120.1(3) . . ?
N1 C8 C9 118.3(3) . . ?
N1 C8 C7 120.1(3) . . ?
C9 C8 C7 121.6(3) . . ?
N2 C7 C1 113.8(3) . . ?
N2 C7 C8 106.0(2) . . ?
C1 C7 C8 111.5(2) . . ?
N2 C7 H7 108.5 . . ?
C1 C7 H7 108.5 . . ?
C8 C7 H7 108.5 . . ?
C6 C1 C2 118.4(3) . . ?
C6 C1 C7 124.5(3) . . ?
C2 C1 C7 117.0(3) . . ?
C10 C9 C14 117.8(3) . . ?
C10 C9 C8 121.6(3) . . ?
C14 C9 C8 120.6(3) . . ?
C20 N2 C7 115.9(3) . . ?
C20 N2 H2A 108(2) . . ?
C7 N2 H2A 119(2) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
O1 C2 C3 123.9(3) . . ?
O1 C2 C1 116.5(3) . . ?
C3 C2 C1 119.6(3) . . ?
C5 C6 C1 122.0(3) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
C16 C15 N1 120.4(3) . . ?
C16 C15 C20 119.5(3) . . ?
N1 C15 C20 119.8(3) . . ?
C12 C13 C14 121.5(4) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
O2 C14 C13 120.0(3) . . ?
O2 C14 C9 120.4(3) . . ?
C13 C14 C9 119.6(3) . . ?
C11 C10 C9 121.3(3) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C19 C20 N2 123.6(3) . . ?
C19 C20 C15 119.5(3) . . ?
N2 C20 C15 116.7(3) . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 118.7(3) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C17 C16 C15 120.1(4) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C13 C12 C11 119.9(4) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C20 C19 C18 120.1(4) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C10 C11 C12 119.7(4) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C19 C18 C17 120.5(4) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C16 C17 C18 120.1(4) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?

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
C15 N1 C8 C9 -174.0(3) . . . . ?
C15 N1 C8 C7 5.7(5) . . . . ?
N1 C8 C7 N2 -38.7(4) . . . . ?
C9 C8 C7 N2 141.0(3) . . . . ?
N1 C8 C7 C1 85.6(4) . . . . ?
C9 C8 C7 C1 -94.7(3) . . . . ?
N2 C7 C1 C6 109.7(3) . . . . ?
C8 C7 C1 C6 -10.1(5) . . . . ?
N2 C7 C1 C2 -68.4(4) . . . . ?
C8 C7 C1 C2 171.8(3) . . . . ?
N1 C8 C9 C10 -176.3(3) . . . . ?
C7 C8 C9 C10 4.0(5) . . . . ?
N1 C8 C9 C14 4.4(5) . . . . ?
C7 C8 C9 C14 -175.3(3) . . . . ?
C1 C7 N2 C20 -70.8(3) . . . . ?
C8 C7 N2 C20 52.1(3) . . . . ?
C4 C3 C2 O1 -179.9(3) . . . . ?
C4 C3 C2 C1 0.0(5) . . . . ?
C6 C1 C2 O1 180.0(3) . . . . ?
C7 C1 C2 O1 -1.8(4) . . . . ?
C6 C1 C2 C3 0.1(5) . . . . ?
C7 C1 C2 C3 178.3(3) . . . . ?
C2 C1 C6 C5 0.0(5) . . . . ?
C7 C1 C6 C5 -178.1(3) . . . . ?
C8 N1 C15 C16 -167.8(3) . . . . ?
C8 N1 C15 C20 17.7(5) . . . . ?
C12 C13 C14 O2 -177.9(4) . . . . ?
C12 C13 C14 C9 3.5(6) . . . . ?
C10 C9 C14 O2 177.4(3) . . . . ?
C8 C9 C14 O2 -3.2(5) . . . . ?
C10 C9 C14 C13 -4.1(5) . . . . ?
C8 C9 C14 C13 175.3(3) . . . . ?
C14 C9 C10 C11 2.6(5) . . . . ?
C8 C9 C10 C11 -176.8(3) . . . . ?
C7 N2 C20 C19 152.1(3) . . . . ?
C7 N2 C20 C15 -33.9(4) . . . . ?
C16 C15 C20 C19 -3.6(5) . . . . ?
N1 C15 C20 C19 170.9(3) . . . . ?
C16 C15 C20 N2 -177.8(3) . . . . ?
N1 C15 C20 N2 -3.3(4) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C1 C6 C5 C4 -0.1(6) . . . . ?
C3 C4 C5 C6 0.2(6) . . . . ?
N1 C15 C16 C17 -173.9(4) . . . . ?
C20 C15 C16 C17 0.6(6) . . . . ?
C14 C13 C12 C11 -1.4(6) . . . . ?
N2 C20 C19 C18 177.6(3) . . . . ?
C15 C20 C19 C18 3.8(5) . . . . ?
C9 C10 C11 C12 -0.5(6) . . . . ?
C13 C12 C11 C10 -0.2(6) . . . . ?
C20 C19 C18 C17 -1.1(6) . . . . ?
C15 C16 C17 C18 2.1(7) . . . . ?
C19 C18 C17 C16 -1.9(7) . . . . ?

_refine_diff_density_max         0.227
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.072

