# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_rp1338
_database_code_depnum_ccdc_archive 'CCDC 2226308'
loop_
_audit_author_name
_audit_author_address
'Srinivasarao Arulananda Babu'
;Indian Institute of Science Education and Research Mohali
India
;
_audit_update_record             
;
2022-12-13 deposited with the CCDC.	2023-01-18 downloaded from the CCDC.
;
_audit_creation_date             2022-12-08
_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        C20H14N2O3
_chemical_formula_moiety         'C20 H14 N2 O3'
_chemical_formula_sum            'C20 H14 N2 O3'
_chemical_formula_weight         330.33
_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.6384(9)
_cell_length_b                   19.8168(19)
_cell_length_c                   9.4404(11)
_cell_angle_alpha                90
_cell_angle_beta                 99.588(10)
_cell_angle_gamma                90
_cell_volume                     1593.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1215
_cell_measurement_temperature    298
_cell_measurement_theta_max      30.3850
_cell_measurement_theta_min      2.9830
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic dark orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5199
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.603
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00 114.00   0.50   20.00    --   29.89  54.00-120.00  362
  2  ω     79.00 104.00   0.50   20.00    --   29.89  54.00  30.00   50
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0047301000
_diffrn_orient_matrix_UB_12      0.0080228000
_diffrn_orient_matrix_UB_13      0.0724192000
_diffrn_orient_matrix_UB_21      0.0419391000
_diffrn_orient_matrix_UB_22      -0.0298990000
_diffrn_orient_matrix_UB_23      0.0229929000
_diffrn_orient_matrix_UB_31      0.0717388000
_diffrn_orient_matrix_UB_32      0.0179729000
_diffrn_orient_matrix_UB_33      0.0059658000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1782
_reflns_number_total             2799
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2799
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.043
_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)+(0.0767P)²+0.0825P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1634
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C20(H20), C7(H7), C4(H4), C13(H13), C14(H14), C3(H3), C16(H16),
 C17(H17), C19(H19), C18(H18)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O3 O 0.73864(17) 0.53246(7) 0.63711(15) 0.0603(4) Uani 1 1 d . . . . .
O1 O 0.81753(19) 0.59596(8) 0.16726(18) 0.0770(5) Uani 1 1 d . . . . .
O2 O 0.7178(2) 0.50267(9) 0.85725(17) 0.0808(6) Uani 1 1 d . . . . .
N2 N 0.0647(2) 0.66227(9) 0.6743(2) 0.0631(5) Uani 1 1 d . . . . .
N3 N -0.0087(2) 0.65941(9) 0.7757(2) 0.0619(5) Uani 1 1 d . . . . .
C5 C 0.5353(2) 0.59545(9) 0.4851(2) 0.0488(5) Uani 1 1 d . . . . .
C8 C 0.4428(2) 0.59606(9) 0.5999(2) 0.0493(5) Uani 1 1 d . . . . .
C15 C -0.1553(2) 0.69485(10) 0.7510(2) 0.0537(5) Uani 1 1 d . . . . .
C9 C 0.5044(2) 0.56562(10) 0.7308(2) 0.0515(5) Uani 1 1 d . . . . .
C6 C 0.6823(2) 0.56445(9) 0.5086(2) 0.0512(5) Uani 1 1 d . . . . .
C11 C 0.2950(2) 0.62696(10) 0.5886(2) 0.0546(5) Uani 1 1 d . . . . .
H11 H 0.2507 0.6474 0.5027 0.065 Uiso 1 1 calc R U . . .
C10 C 0.6573(3) 0.53167(11) 0.7503(2) 0.0577(6) Uani 1 1 d . . . . .
C20 C -0.2372(3) 0.69409(11) 0.8636(2) 0.0624(6) Uani 1 1 d . . . . .
H20 H -0.1976 0.6706 0.9472 0.075 Uiso 1 1 calc R U . . .
C12 C 0.2150(2) 0.62741(10) 0.7029(2) 0.0559(6) Uani 1 1 d . . . . .
C7 C 0.7804(2) 0.56305(10) 0.4066(2) 0.0565(6) Uani 1 1 d . . . . .
H7 H 0.8772 0.5415 0.4258 0.068 Uiso 1 1 calc R U . . .
C2 C 0.7324(3) 0.59407(10) 0.2764(2) 0.0592(6) Uani 1 1 d . . . . .
C4 C 0.4921(3) 0.62663(11) 0.3513(2) 0.0602(6) Uani 1 1 d . . . . .
H4 H 0.3954 0.6483 0.3312 0.072 Uiso 1 1 calc R U . . .
C13 C 0.2780(3) 0.59808(11) 0.8336(3) 0.0646(6) Uani 1 1 d . . . . .
H13 H 0.2238 0.5992 0.9107 0.078 Uiso 1 1 calc R U . . .
C14 C 0.4222(3) 0.56735(11) 0.8462(2) 0.0637(6) Uani 1 1 d . . . . .
H14 H 0.4657 0.5474 0.9329 0.076 Uiso 1 1 calc R U . . .
C3 C 0.5872(3) 0.62632(11) 0.2492(3) 0.0650(6) Uani 1 1 d . . . . .
H3 H 0.5549 0.6477 0.1615 0.078 Uiso 1 1 calc R U . . .
C16 C -0.2151(3) 0.72893(11) 0.6254(2) 0.0642(6) Uani 1 1 d . . . . .
H16 H -0.1608 0.7290 0.5482 0.077 Uiso 1 1 calc R U . . .
C17 C -0.3557(3) 0.76266(12) 0.6162(3) 0.0729(7) Uani 1 1 d . . . . .
H17 H -0.3961 0.7861 0.5329 0.087 Uiso 1 1 calc R U . . .
C19 C -0.3777(3) 0.72794(12) 0.8534(3) 0.0706(7) Uani 1 1 d . . . . .
H19 H -0.4325 0.7277 0.9303 0.085 Uiso 1 1 calc R U . . .
C18 C -0.4369(3) 0.76184(12) 0.7303(3) 0.0706(7) Uani 1 1 d . . . . .
H18 H -0.5322 0.7844 0.7233 0.085 Uiso 1 1 calc R U . . .
C1 C 0.9626(3) 0.55985(14) 0.1830(3) 0.0834(8) Uani 1 1 d . . . . .
H1A H 1.0066 0.5640 0.0964 0.125 Uiso 1 1 calc R U . . .
H1B H 0.9442 0.5131 0.2009 0.125 Uiso 1 1 calc R U . . .
H1C H 1.0345 0.5782 0.2621 0.125 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
O3 C6 1.383(2) . ?
O3 C10 1.373(2) . ?
O1 C2 1.362(2) . ?
O1 C1 1.429(3) . ?
O2 C10 1.203(2) . ?
N2 N3 1.235(2) . ?
N2 C12 1.455(3) . ?
N3 C15 1.433(3) . ?
C5 C8 1.450(3) . ?
C5 C6 1.394(3) . ?
C5 C4 1.400(3) . ?
C8 C9 1.398(3) . ?
C8 C11 1.403(3) . ?
C15 C20 1.372(3) . ?
C15 C16 1.388(3) . ?
C9 C10 1.466(3) . ?
C9 C14 1.397(3) . ?
C6 C7 1.385(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(3) . ?
C20 H20 0.9300 . ?
C20 C19 1.377(3) . ?
C12 C13 1.390(3) . ?
C7 H7 0.9300 . ?
C7 C2 1.375(3) . ?
C2 C3 1.393(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.367(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(3) . ?
C14 H14 0.9300 . ?
C3 H3 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.376(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.366(3) . ?
C18 H18 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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
C10 O3 C6 122.43(16) . . ?
C2 O1 C1 118.82(19) . . ?
N3 N2 C12 113.04(19) . . ?
N2 N3 C15 113.93(18) . . ?
C6 C5 C8 119.03(18) . . ?
C6 C5 C4 115.92(19) . . ?
C4 C5 C8 124.98(18) . . ?
C9 C8 C5 118.71(18) . . ?
C9 C8 C11 117.62(19) . . ?
C11 C8 C5 123.65(18) . . ?
C20 C15 N3 115.10(19) . . ?
C20 C15 C16 120.1(2) . . ?
C16 C15 N3 124.8(2) . . ?
C8 C9 C10 120.78(19) . . ?
C14 C9 C8 120.67(19) . . ?
C14 C9 C10 118.55(19) . . ?
O3 C6 C5 121.32(18) . . ?
O3 C6 C7 115.70(18) . . ?
C7 C6 C5 122.98(19) . . ?
C8 C11 H11 119.6 . . ?
C12 C11 C8 120.8(2) . . ?
C12 C11 H11 119.6 . . ?
O3 C10 C9 117.66(18) . . ?
O2 C10 O3 116.84(19) . . ?
O2 C10 C9 125.5(2) . . ?
C15 C20 H20 119.9 . . ?
C15 C20 C19 120.2(2) . . ?
C19 C20 H20 119.9 . . ?
C11 C12 N2 114.0(2) . . ?
C11 C12 C13 121.3(2) . . ?
C13 C12 N2 124.7(2) . . ?
C6 C7 H7 120.5 . . ?
C2 C7 C6 119.0(2) . . ?
C2 C7 H7 120.5 . . ?
O1 C2 C7 124.6(2) . . ?
O1 C2 C3 115.5(2) . . ?
C7 C2 C3 119.9(2) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 C5 122.2(2) . . ?
C3 C4 H4 118.9 . . ?
C12 C13 H13 120.7 . . ?
C14 C13 C12 118.6(2) . . ?
C14 C13 H13 120.7 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 121.0(2) . . ?
C13 C14 H14 119.5 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 120.0 . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.3(2) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 C20 120.0(2) . . ?
C18 C19 H19 120.0 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

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
O3 C6 C7 C2 -179.74(17) . . . . ?
O1 C2 C3 C4 179.3(2) . . . . ?
N2 N3 C15 C20 -178.23(19) . . . . ?
N2 N3 C15 C16 1.1(3) . . . . ?
N2 C12 C13 C14 -179.29(19) . . . . ?
N3 N2 C12 C11 176.79(18) . . . . ?
N3 N2 C12 C13 -4.8(3) . . . . ?
N3 C15 C20 C19 178.36(19) . . . . ?
N3 C15 C16 C17 -178.25(19) . . . . ?
C5 C8 C9 C10 -2.1(3) . . . . ?
C5 C8 C9 C14 177.44(19) . . . . ?
C5 C8 C11 C12 -178.17(19) . . . . ?
C5 C6 C7 C2 0.7(3) . . . . ?
C5 C4 C3 C2 0.2(4) . . . . ?
C8 C5 C6 O3 2.2(3) . . . . ?
C8 C5 C6 C7 -178.21(18) . . . . ?
C8 C5 C4 C3 177.6(2) . . . . ?
C8 C9 C10 O3 1.6(3) . . . . ?
C8 C9 C10 O2 -178.0(2) . . . . ?
C8 C9 C14 C13 0.9(3) . . . . ?
C8 C11 C12 N2 179.18(17) . . . . ?
C8 C11 C12 C13 0.7(3) . . . . ?
C15 C20 C19 C18 0.7(3) . . . . ?
C15 C16 C17 C18 -0.8(3) . . . . ?
C9 C8 C11 C12 0.4(3) . . . . ?
C6 O3 C10 O2 -179.58(18) . . . . ?
C6 O3 C10 C9 0.8(3) . . . . ?
C6 C5 C8 C9 0.2(3) . . . . ?
C6 C5 C8 C11 178.71(18) . . . . ?
C6 C5 C4 C3 0.5(3) . . . . ?
C6 C7 C2 O1 -179.69(19) . . . . ?
C6 C7 C2 C3 0.1(3) . . . . ?
C11 C8 C9 C10 179.29(18) . . . . ?
C11 C8 C9 C14 -1.2(3) . . . . ?
C11 C12 C13 C14 -1.0(3) . . . . ?
C10 O3 C6 C5 -2.8(3) . . . . ?
C10 O3 C6 C7 177.66(18) . . . . ?
C10 C9 C14 C13 -179.6(2) . . . . ?
C20 C15 C16 C17 1.0(3) . . . . ?
C20 C19 C18 C17 -0.4(3) . . . . ?
C12 N2 N3 C15 178.55(16) . . . . ?
C12 C13 C14 C9 0.2(3) . . . . ?
C7 C2 C3 C4 -0.5(3) . . . . ?
C4 C5 C8 C9 -176.78(19) . . . . ?
C4 C5 C8 C11 1.8(3) . . . . ?
C4 C5 C6 O3 179.45(17) . . . . ?
C4 C5 C6 C7 -1.0(3) . . . . ?
C14 C9 C10 O3 -177.88(19) . . . . ?
C14 C9 C10 O2 2.5(3) . . . . ?
C16 C15 C20 C19 -1.0(3) . . . . ?
C16 C17 C18 C19 0.5(4) . . . . ?
C1 O1 C2 C7 4.3(3) . . . . ?
C1 O1 C2 C3 -175.5(2) . . . . ?

_olex2_submission_original_sample_id 'rp 1338'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.058
_oxdiff_exptl_absorpt_empirical_full_min 0.943
