# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# 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_ns172
_database_code_depnum_ccdc_archive 'CCDC 2236979'
loop_
_audit_author_name
_audit_author_address
'Mayank Joshi'
;Indian Institute of Science Education and Research Mohali
India
;
_audit_update_record             
;
2023-01-18 deposited with the CCDC.	2023-03-22 downloaded from the CCDC.
;
_audit_creation_date             2023-01-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 N2 O2'
_chemical_formula_sum            'C20 H14 N2 O2'
_chemical_formula_weight         314.33
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   13.4145(5)
_cell_length_b                   10.6112(4)
_cell_length_c                   11.6042(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.3990(10)
_cell_angle_gamma                90
_cell_volume                     1558.01(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3883
_cell_measurement_temperature    296.0(2)
_cell_measurement_theta_max      20.20
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            40495
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.347
_diffrn_reflns_theta_min         2.505
_diffrn_ambient_temperature      296.0(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2742
_reflns_number_total             3883
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3883
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0567P)²+0.2998P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1232
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.20179(8) 0.53628(9) 0.62963(9) 0.0420(3) Uani 1 1 d . . . . .
C1 C 0.12442(10) 0.62912(12) 0.58870(12) 0.0348(3) Uani 1 1 d . . . . .
O2 O 0.37458(11) 1.14698(12) 0.40121(11) 0.0623(4) Uani 1 1 d . . . . .
C13 C 0.28914(11) 0.54297(13) 0.59667(12) 0.0380(3) Uani 1 1 d . . . . .
C10 C 0.13438(11) 0.72907(13) 0.52020(12) 0.0374(3) Uani 1 1 d . . . . .
N1 N 0.35147(12) 0.44319(13) 0.63905(14) 0.0524(4) Uani 1 1 d . . . . .
C3 C 0.02163(13) 0.50154(16) 0.69091(13) 0.0449(4) Uani 1 1 d . . . . .
C17 C 0.35999(11) 1.06789(13) 0.48797(13) 0.0419(3) Uani 1 1 d . . . . .
C12 C 0.30646(11) 0.63927(13) 0.52858(12) 0.0383(3) Uani 1 1 d . . . . .
C15 C 0.28607(11) 0.87314(13) 0.52787(12) 0.0366(3) Uani 1 1 d . . . . .
C2 C 0.03347(11) 0.60788(13) 0.62263(12) 0.0376(3) Uani 1 1 d . . . . .
C18 C 0.39645(12) 1.09564(15) 0.61088(15) 0.0464(4) Uani 1 1 d . . . . .
C7 C -0.04985(11) 0.69664(15) 0.58249(14) 0.0464(4) Uani 1 1 d . . . . .
N2 N 0.48100(12) 0.65107(13) 0.48506(14) 0.0581(4) Uani 1 1 d . . . . .
C11 C 0.23104(11) 0.74805(13) 0.48273(12) 0.0373(3) Uani 1 1 d . . . . .
C14 C 0.40306(12) 0.64315(13) 0.50541(14) 0.0431(3) Uani 1 1 d . . . . .
C8 C -0.03956(13) 0.79949(17) 0.50945(16) 0.0550(4) Uani 1 1 d . . . . .
C9 C 0.04923(13) 0.81443(16) 0.47985(15) 0.0493(4) Uani 1 1 d . . . . .
C16 C 0.30494(12) 0.95700(14) 0.44675(13) 0.0407(3) Uani 1 1 d . . . . .
C4 C -0.06861(14) 0.48738(19) 0.71990(15) 0.0550(4) Uani 1 1 d . . . . .
C20 C 0.32261(13) 0.90150(15) 0.65180(14) 0.0460(4) Uani 1 1 d . . . . .
C6 C -0.14063(13) 0.6786(2) 0.61688(18) 0.0602(5) Uani 1 1 d . . . . .
C5 C -0.14909(14) 0.5771(2) 0.68396(16) 0.0629(5) Uani 1 1 d . . . . .
C19 C 0.37688(13) 1.01210(16) 0.69220(15) 0.0492(4) Uani 1 1 d . . . . .
H3 H 0.0773(14) 0.4371(18) 0.7134(15) 0.055(5) Uiso 1 1 d . . . . .
H11 H 0.2069(12) 0.7501(14) 0.3900(14) 0.042(4) Uiso 1 1 d . . . . .
H4 H -0.0777(15) 0.412(2) 0.7642(17) 0.072(6) Uiso 1 1 d . . . . .
H20 H 0.3118(14) 0.8412(17) 0.7095(16) 0.060(5) Uiso 1 1 d . . . . .
H8 H -0.0980(15) 0.8586(17) 0.4815(16) 0.062(5) Uiso 1 1 d . . . . .
H9 H 0.0558(14) 0.8846(18) 0.4308(15) 0.063(5) Uiso 1 1 d . . . . .
H19 H 0.4008(14) 1.0319(18) 0.7792(18) 0.070(5) Uiso 1 1 d . . . . .
H16 H 0.2772(12) 0.9373(15) 0.3582(14) 0.048(4) Uiso 1 1 d . . . . .
H1A H 0.3432(15) 0.4019(19) 0.7039(18) 0.072(6) Uiso 1 1 d . . . . .
H18 H 0.4332(14) 1.1732(19) 0.6392(16) 0.064(5) Uiso 1 1 d . . . . .
H5 H -0.2121(17) 0.565(2) 0.7063(18) 0.080(6) Uiso 1 1 d . . . . .
H1B H 0.4113(17) 0.432(2) 0.6218(19) 0.081(6) Uiso 1 1 d . . . . .
H6 H -0.1933(18) 0.740(2) 0.5882(19) 0.085(7) Uiso 1 1 d . . . . .
H2 H 0.4182(19) 1.213(2) 0.442(2) 0.096(7) Uiso 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
O1 C1 1.3950(16) . ?
O1 C13 1.3498(16) . ?
C1 C10 1.3584(19) . ?
C1 C2 1.4189(19) . ?
O2 C17 1.3738(17) . ?
O2 H2 0.93(3) . ?
C13 N1 1.3375(19) . ?
C13 C12 1.3580(19) . ?
C10 C11 1.5118(19) . ?
C10 C9 1.410(2) . ?
N1 H1A 0.91(2) . ?
N1 H1B 0.90(2) . ?
C3 C2 1.418(2) . ?
C3 C4 1.368(2) . ?
C3 H3 0.981(18) . ?
C17 C18 1.377(2) . ?
C17 C16 1.387(2) . ?
C12 C11 1.510(2) . ?
C12 C14 1.409(2) . ?
C15 C11 1.5245(18) . ?
C15 C16 1.3785(19) . ?
C15 C20 1.390(2) . ?
C2 C7 1.417(2) . ?
C18 C19 1.382(2) . ?
C18 H18 0.96(2) . ?
C7 C8 1.416(2) . ?
C7 C6 1.415(2) . ?
N2 C14 1.1489(19) . ?
C11 H11 1.016(15) . ?
C8 C9 1.354(2) . ?
C8 H8 0.972(19) . ?
C9 H9 0.959(18) . ?
C16 H16 0.992(16) . ?
C4 C5 1.395(3) . ?
C4 H4 0.98(2) . ?
C20 C19 1.379(2) . ?
C20 H20 0.971(18) . ?
C6 C5 1.355(3) . ?
C6 H6 0.94(2) . ?
C5 H5 0.97(2) . ?
C19 H19 0.976(19) . ?

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
C13 O1 C1 118.95(10) . . ?
O1 C1 C2 113.86(11) . . ?
C10 C1 O1 122.96(12) . . ?
C10 C1 C2 123.17(13) . . ?
C17 O2 H2 107.6(14) . . ?
O1 C13 C12 122.47(13) . . ?
N1 C13 O1 110.46(13) . . ?
N1 C13 C12 127.06(14) . . ?
C1 C10 C11 122.19(13) . . ?
C1 C10 C9 118.00(14) . . ?
C9 C10 C11 119.76(13) . . ?
C13 N1 H1A 116.9(12) . . ?
C13 N1 H1B 121.0(14) . . ?
H1A N1 H1B 119.2(19) . . ?
C2 C3 H3 119.1(10) . . ?
C4 C3 C2 119.83(17) . . ?
C4 C3 H3 121.0(10) . . ?
O2 C17 C18 122.71(13) . . ?
O2 C17 C16 117.04(13) . . ?
C18 C17 C16 120.25(13) . . ?
C13 C12 C11 123.78(12) . . ?
C13 C12 C14 118.62(13) . . ?
C14 C12 C11 117.48(12) . . ?
C16 C15 C11 120.35(12) . . ?
C16 C15 C20 119.03(13) . . ?
C20 C15 C11 120.54(12) . . ?
C3 C2 C1 123.22(13) . . ?
C7 C2 C1 117.41(13) . . ?
C7 C2 C3 119.35(14) . . ?
C17 C18 C19 119.17(14) . . ?
C17 C18 H18 120.2(11) . . ?
C19 C18 H18 120.6(11) . . ?
C8 C7 C2 119.07(14) . . ?
C6 C7 C2 118.44(16) . . ?
C6 C7 C8 122.49(16) . . ?
C10 C11 C15 112.39(11) . . ?
C10 C11 H11 107.8(9) . . ?
C12 C11 C10 109.57(11) . . ?
C12 C11 C15 110.68(11) . . ?
C12 C11 H11 109.3(8) . . ?
C15 C11 H11 107.0(8) . . ?
N2 C14 C12 177.34(16) . . ?
C7 C8 H8 118.0(11) . . ?
C9 C8 C7 120.72(15) . . ?
C9 C8 H8 121.3(11) . . ?
C10 C9 H9 118.2(11) . . ?
C8 C9 C10 121.61(15) . . ?
C8 C9 H9 120.2(11) . . ?
C17 C16 H16 120.6(9) . . ?
C15 C16 C17 120.63(13) . . ?
C15 C16 H16 118.7(9) . . ?
C3 C4 C5 120.76(17) . . ?
C3 C4 H4 119.7(12) . . ?
C5 C4 H4 119.6(12) . . ?
C15 C20 H20 119.3(10) . . ?
C19 C20 C15 120.08(14) . . ?
C19 C20 H20 120.6(10) . . ?
C7 C6 H6 115.1(13) . . ?
C5 C6 C7 120.90(18) . . ?
C5 C6 H6 124.0(13) . . ?
C4 C5 H5 119.1(13) . . ?
C6 C5 C4 120.65(17) . . ?
C6 C5 H5 120.2(13) . . ?
C18 C19 H19 119.8(12) . . ?
C20 C19 C18 120.83(15) . . ?
C20 C19 H19 119.4(12) . . ?

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
O1 C1 C10 C11 -0.1(2) . . . . ?
O1 C1 C10 C9 177.51(12) . . . . ?
O1 C1 C2 C3 -0.55(18) . . . . ?
O1 C1 C2 C7 -178.77(11) . . . . ?
O1 C13 C12 C11 0.0(2) . . . . ?
O1 C13 C12 C14 175.74(12) . . . . ?
C1 O1 C13 N1 -176.89(12) . . . . ?
C1 O1 C13 C12 2.40(19) . . . . ?
C1 C10 C11 C12 2.21(18) . . . . ?
C1 C10 C11 C15 -121.28(14) . . . . ?
C1 C10 C9 C8 1.0(2) . . . . ?
C1 C2 C7 C8 1.2(2) . . . . ?
C1 C2 C7 C6 -178.97(13) . . . . ?
O2 C17 C18 C19 178.85(15) . . . . ?
O2 C17 C16 C15 -179.37(14) . . . . ?
C13 O1 C1 C10 -2.33(18) . . . . ?
C13 O1 C1 C2 176.21(11) . . . . ?
C13 C12 C11 C10 -2.18(18) . . . . ?
C13 C12 C11 C15 122.32(14) . . . . ?
C10 C1 C2 C3 177.98(13) . . . . ?
C10 C1 C2 C7 -0.24(19) . . . . ?
N1 C13 C12 C11 179.14(14) . . . . ?
N1 C13 C12 C14 -5.1(2) . . . . ?
C3 C2 C7 C8 -177.06(14) . . . . ?
C3 C2 C7 C6 2.7(2) . . . . ?
C3 C4 C5 C6 1.7(3) . . . . ?
C17 C18 C19 C20 0.7(2) . . . . ?
C15 C20 C19 C18 -0.5(3) . . . . ?
C2 C1 C10 C11 -178.55(12) . . . . ?
C2 C1 C10 C9 -0.9(2) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C2 C7 C8 C9 -1.1(2) . . . . ?
C2 C7 C6 C5 -1.7(2) . . . . ?
C18 C17 C16 C15 -0.1(2) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C7 C6 C5 C4 -0.5(3) . . . . ?
C11 C10 C9 C8 178.76(14) . . . . ?
C11 C15 C16 C17 -176.51(13) . . . . ?
C11 C15 C20 C19 176.78(14) . . . . ?
C14 C12 C11 C10 -177.98(12) . . . . ?
C14 C12 C11 C15 -53.48(16) . . . . ?
C8 C7 C6 C5 178.10(17) . . . . ?
C9 C10 C11 C12 -175.40(12) . . . . ?
C9 C10 C11 C15 61.10(17) . . . . ?
C16 C17 C18 C19 -0.4(2) . . . . ?
C16 C15 C11 C10 -125.17(14) . . . . ?
C16 C15 C11 C12 111.96(14) . . . . ?
C16 C15 C20 C19 0.0(2) . . . . ?
C4 C3 C2 C1 -179.83(13) . . . . ?
C4 C3 C2 C7 -1.6(2) . . . . ?
C20 C15 C11 C10 58.09(18) . . . . ?
C20 C15 C11 C12 -64.78(17) . . . . ?
C20 C15 C16 C17 0.3(2) . . . . ?
C6 C7 C8 C9 179.10(16) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
