# 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_gh
_database_code_depnum_ccdc_archive 'CCDC 2193978'
loop_
_audit_author_name
_audit_author_address
'Vishal Sharma'
;National Chemical Laboratory
India
;
_audit_update_record             
;
2022-08-01 deposited with the CCDC.	2023-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H16 N2 O2'
_chemical_formula_weight         340.37

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.4049(9)
_cell_length_b                   13.3896(12)
_cell_length_c                   12.7634(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.507(4)
_cell_angle_gamma                90
_cell_volume                     1606.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9820
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      28.72

_exptl_crystal_description       Block
_exptl_crystal_colour            'reddish yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45851
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.647
_diffrn_reflns_theta_max         28.740
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4126
_reflns_number_gt                3780
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0660P)²+0.7523P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4126
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1209
_refine_ls_wR_factor_gt          0.1175
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.47122(8) 0.27225(6) 0.81664(6) 0.01556(18) Uani 1 1 d . . . . .
H1 H 0.431531 0.217680 0.829996 0.023 Uiso 1 1 calc R U . . .
O2 O 0.38815(9) 0.39433(6) 0.43295(6) 0.01634(18) Uani 1 1 d . . . . .
N2 N 0.42477(10) 0.39994(7) 0.65286(7) 0.0147(2) Uani 1 1 d . . . . .
H2 H 0.440414 0.404863 0.720944 0.018 Uiso 1 1 calc R U . . .
N1 N 0.15685(9) 0.59666(6) 0.60946(7) 0.01210(18) Uani 1 1 d . . . . .
C19 C 0.19582(12) 0.59115(8) 0.94240(9) 0.0175(2) Uani 1 1 d . . . . .
H19 H 0.118439 0.598615 0.988123 0.021 Uiso 1 1 calc R U . . .
C22 C 0.42255(11) 0.56748(8) 0.80897(8) 0.0147(2) Uani 1 1 d . . . . .
H22 H 0.500277 0.558877 0.763777 0.018 Uiso 1 1 calc R U . . .
C18 C 0.17011(11) 0.56973(8) 0.83681(8) 0.0141(2) Uani 1 1 d . . . . .
H18 H 0.075043 0.563906 0.810490 0.017 Uiso 1 1 calc R U . . .
C2 C 0.57920(11) 0.25431(8) 0.64356(8) 0.0128(2) Uani 1 1 d . . . . .
C11 C 0.19440(11) 0.52423(8) 0.33027(8) 0.0140(2) Uani 1 1 d . . . . .
H11 H 0.249876 0.482114 0.287550 0.017 Uiso 1 1 calc R U . . .
C5 C 0.55167(12) 0.26025(8) 0.42457(8) 0.0154(2) Uani 1 1 d . . . . .
H5 H 0.541690 0.262643 0.350354 0.018 Uiso 1 1 calc R U . . .
C8 C 0.33227(11) 0.46543(7) 0.60093(8) 0.0118(2) Uani 1 1 d . . . . .
C21 C 0.44773(12) 0.59056(8) 0.91375(9) 0.0176(2) Uani 1 1 d . . . . .
H21 H 0.542542 0.598879 0.939809 0.021 Uiso 1 1 calc R U . . .
C17 C 0.28301(11) 0.55678(7) 0.76951(8) 0.0118(2) Uani 1 1 d . . . . .
C6 C 0.47749(11) 0.32623(8) 0.48573(8) 0.0128(2) Uani 1 1 d . . . . .
C16 C 0.25472(11) 0.53934(7) 0.65573(8) 0.0112(2) Uani 1 1 d . . . . .
C10 C 0.21656(11) 0.52384(8) 0.44086(8) 0.0120(2) Uani 1 1 d . . . . .
C1 C 0.59876(11) 0.25383(8) 0.76163(8) 0.0155(2) Uani 1 1 d . . . . .
H1A H 0.637505 0.188156 0.783704 0.019 Uiso 1 1 calc R U . . .
H1B H 0.669831 0.305318 0.781942 0.019 Uiso 1 1 calc R U . . .
C9 C 0.31425(11) 0.46063(8) 0.49347(8) 0.0122(2) Uani 1 1 d . . . . .
C12 C 0.09320(12) 0.58522(8) 0.28523(8) 0.0159(2) Uani 1 1 d . . . . .
H12 H 0.079572 0.585650 0.211214 0.019 Uiso 1 1 calc R U . . .
C3 C 0.65258(11) 0.18672(8) 0.58160(9) 0.0160(2) Uani 1 1 d . . . . .
H3 H 0.711276 0.137510 0.614442 0.019 Uiso 1 1 calc R U . . .
C7 C 0.49240(11) 0.32615(7) 0.59482(8) 0.0123(2) Uani 1 1 d . . . . .
C4 C 0.64147(12) 0.18998(8) 0.47266(9) 0.0171(2) Uani 1 1 d . . . . .
H4 H 0.694427 0.144873 0.431512 0.021 Uiso 1 1 calc R U . . .
C14 C 0.02969(11) 0.65002(8) 0.45461(8) 0.0154(2) Uani 1 1 d . . . . .
H14 H -0.026739 0.692743 0.495978 0.018 Uiso 1 1 calc R U . . .
C20 C 0.33441(13) 0.60159(9) 0.98086(9) 0.0188(2) Uani 1 1 d . . . . .
H20 H 0.351959 0.616239 1.052874 0.023 Uiso 1 1 calc R U . . .
C15 C 0.13510(11) 0.58907(7) 0.50334(8) 0.0121(2) Uani 1 1 d . . . . .
C13 C 0.00870(12) 0.64763(8) 0.34789(9) 0.0165(2) Uani 1 1 d . . . . .
H13 H -0.063041 0.688139 0.315814 0.020 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 C1 1.4271(13) . ?
O1 H1 0.8400 . ?
O2 C9 1.3770(12) . ?
O2 C6 1.4005(13) . ?
N2 C8 1.3909(13) . ?
N2 C7 1.3980(13) . ?
N2 H2 0.8800 . ?
N1 C16 1.3254(13) . ?
N1 C15 1.3682(13) . ?
C19 C20 1.3877(17) . ?
C19 C18 1.3928(15) . ?
C19 H19 0.9500 . ?
C22 C21 1.3868(15) . ?
C22 C17 1.4007(15) . ?
C22 H22 0.9500 . ?
C18 C17 1.3940(14) . ?
C18 H18 0.9500 . ?
C2 C3 1.3962(14) . ?
C2 C7 1.3971(14) . ?
C2 C1 1.5134(14) . ?
C11 C12 1.3691(15) . ?
C11 C10 1.4214(14) . ?
C11 H11 0.9500 . ?
C5 C6 1.3803(14) . ?
C5 C4 1.3956(16) . ?
C5 H5 0.9500 . ?
C8 C9 1.3791(14) . ?
C8 C16 1.4238(14) . ?
C21 C20 1.3927(16) . ?
C21 H21 0.9500 . ?
C17 C16 1.4880(13) . ?
C6 C7 1.3958(14) . ?
C10 C9 1.4067(14) . ?
C10 C15 1.4205(14) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C12 C13 1.4152(16) . ?
C12 H12 0.9500 . ?
C3 C4 1.3923(15) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C14 C13 1.3716(15) . ?
C14 C15 1.4153(14) . ?
C14 H14 0.9500 . ?
C20 H20 0.9500 . ?
C13 H13 0.9500 . ?

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
C1 O1 H1 109.5 . . ?
C9 O2 C6 117.08(8) . . ?
C8 N2 C7 118.73(9) . . ?
C8 N2 H2 120.6 . . ?
C7 N2 H2 120.6 . . ?
C16 N1 C15 118.82(9) . . ?
C20 C19 C18 120.04(10) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C22 C17 120.27(10) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?
C19 C18 C17 120.41(10) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C3 C2 C7 119.07(10) . . ?
C3 C2 C1 120.82(9) . . ?
C7 C2 C1 120.04(9) . . ?
C12 C11 C10 120.09(10) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C6 C5 C4 119.46(10) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C9 C8 N2 120.23(9) . . ?
C9 C8 C16 118.02(9) . . ?
N2 C8 C16 121.75(9) . . ?
C22 C21 C20 120.18(10) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C18 C17 C22 119.17(9) . . ?
C18 C17 C16 120.09(9) . . ?
C22 C17 C16 120.58(9) . . ?
C5 C6 C7 121.64(10) . . ?
C5 C6 O2 116.78(9) . . ?
C7 C6 O2 121.57(9) . . ?
N1 C16 C8 122.85(9) . . ?
N1 C16 C17 116.63(9) . . ?
C8 C16 C17 120.51(9) . . ?
C9 C10 C15 117.20(9) . . ?
C9 C10 C11 123.58(9) . . ?
C15 C10 C11 119.21(9) . . ?
O1 C1 C2 114.04(8) . . ?
O1 C1 H1A 108.7 . . ?
C2 C1 H1A 108.7 . . ?
O1 C1 H1B 108.7 . . ?
C2 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
O2 C9 C8 122.50(9) . . ?
O2 C9 C10 116.94(9) . . ?
C8 C9 C10 120.56(9) . . ?
C11 C12 C13 120.63(10) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C4 C3 C2 121.34(10) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C6 C7 C2 119.14(9) . . ?
C6 C7 N2 119.53(9) . . ?
C2 C7 N2 121.29(9) . . ?
C3 C4 C5 119.27(10) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C13 C14 C15 120.26(10) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C19 C20 C21 119.91(10) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
N1 C15 C14 118.49(9) . . ?
N1 C15 C10 122.18(9) . . ?
C14 C15 C10 119.32(9) . . ?
C14 C13 C12 120.44(10) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?

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
C20 C19 C18 C17 1.21(17) . . . . ?
C7 N2 C8 C9 -3.51(15) . . . . ?
C7 N2 C8 C16 177.02(9) . . . . ?
C17 C22 C21 C20 1.10(17) . . . . ?
C19 C18 C17 C22 -1.21(16) . . . . ?
C19 C18 C17 C16 -176.71(10) . . . . ?
C21 C22 C17 C18 0.06(16) . . . . ?
C21 C22 C17 C16 175.53(10) . . . . ?
C4 C5 C6 C7 1.52(16) . . . . ?
C4 C5 C6 O2 -179.43(9) . . . . ?
C9 O2 C6 C5 -179.75(9) . . . . ?
C9 O2 C6 C7 -0.71(14) . . . . ?
C15 N1 C16 C8 -4.13(15) . . . . ?
C15 N1 C16 C17 174.80(9) . . . . ?
C9 C8 C16 N1 6.62(15) . . . . ?
N2 C8 C16 N1 -173.90(9) . . . . ?
C9 C8 C16 C17 -172.27(9) . . . . ?
N2 C8 C16 C17 7.22(15) . . . . ?
C18 C17 C16 N1 44.30(13) . . . . ?
C22 C17 C16 N1 -131.13(10) . . . . ?
C18 C17 C16 C8 -136.74(10) . . . . ?
C22 C17 C16 C8 47.83(14) . . . . ?
C12 C11 C10 C9 177.38(10) . . . . ?
C12 C11 C10 C15 -1.54(15) . . . . ?
C3 C2 C1 O1 -141.79(10) . . . . ?
C7 C2 C1 O1 41.44(13) . . . . ?
C6 O2 C9 C8 3.98(14) . . . . ?
C6 O2 C9 C10 -175.33(9) . . . . ?
N2 C8 C9 O2 -1.91(15) . . . . ?
C16 C8 C9 O2 177.59(9) . . . . ?
N2 C8 C9 C10 177.38(9) . . . . ?
C16 C8 C9 C10 -3.13(15) . . . . ?
C15 C10 C9 O2 177.07(9) . . . . ?
C11 C10 C9 O2 -1.86(15) . . . . ?
C15 C10 C9 C8 -2.25(15) . . . . ?
C11 C10 C9 C8 178.82(9) . . . . ?
C10 C11 C12 C13 -0.65(16) . . . . ?
C7 C2 C3 C4 0.37(16) . . . . ?
C1 C2 C3 C4 -176.44(10) . . . . ?
C5 C6 C7 C2 -3.19(15) . . . . ?
O2 C6 C7 C2 177.81(9) . . . . ?
C5 C6 C7 N2 174.43(10) . . . . ?
O2 C6 C7 N2 -4.57(15) . . . . ?
C3 C2 C7 C6 2.20(15) . . . . ?
C1 C2 C7 C6 179.04(9) . . . . ?
C3 C2 C7 N2 -175.37(10) . . . . ?
C1 C2 C7 N2 1.46(15) . . . . ?
C8 N2 C7 C6 6.61(15) . . . . ?
C8 N2 C7 C2 -175.83(9) . . . . ?
C2 C3 C4 C5 -2.03(16) . . . . ?
C6 C5 C4 C3 1.09(16) . . . . ?
C18 C19 C20 C21 -0.04(17) . . . . ?
C22 C21 C20 C19 -1.11(17) . . . . ?
C16 N1 C15 C14 179.55(9) . . . . ?
C16 N1 C15 C10 -1.76(15) . . . . ?
C13 C14 C15 N1 177.30(9) . . . . ?
C13 C14 C15 C10 -1.42(15) . . . . ?
C9 C10 C15 N1 4.91(15) . . . . ?
C11 C10 C15 N1 -176.11(9) . . . . ?
C9 C10 C15 C14 -176.42(9) . . . . ?
C11 C10 C15 C14 2.57(15) . . . . ?
C15 C14 C13 C12 -0.77(16) . . . . ?
C11 C12 C13 C14 1.84(16) . . . . ?

_refine_diff_density_max         0.537
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.052

