# 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_compound1
_database_code_depnum_ccdc_archive 'CCDC 2223355'
loop_
_audit_author_name
_audit_author_address
'Snehadrinarayan Khatua'
;North Eastern Hill University
India
;
_audit_update_record             
;
2023-07-08 deposited with the CCDC.	2023-07-17 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            'C20 H14 N2 O'
_chemical_formula_weight         298.33

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                   15.1687(11)
_cell_length_b                   15.6842(10)
_cell_length_c                   6.4380(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.468(2)
_cell_angle_gamma                90
_cell_volume                     1501.08(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3485
_cell_measurement_theta_min      2.937
_cell_measurement_theta_max      30.662

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\^A?S DIAMOND microfocus Mo tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Photon III detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32645
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.937
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2622
_reflns_number_gt                2103
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.0364P)²+0.5758P] 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         2622
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.1119
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
C1 C 0.77219(14) 0.58099(11) 0.1998(3) 0.0477(5) Uani 1 1 d . . . . .
C2 C 0.84276(16) 0.62126(13) 0.1339(3) 0.0595(6) Uani 1 1 d . . . . .
H2 H 0.900906 0.616099 0.212907 0.071 Uiso 1 1 calc R U . . .
C3 C 0.82685(18) 0.66914(14) -0.0492(4) 0.0697(7) Uani 1 1 d . . . . .
H3 H 0.874365 0.696547 -0.093056 0.084 Uiso 1 1 calc R U . . .
C4 C 0.74133(19) 0.67659(15) -0.1671(4) 0.0737(7) Uani 1 1 d . . . . .
H4 H 0.730604 0.709212 -0.290228 0.088 Uiso 1 1 calc R U . . .
C5 C 0.67175(18) 0.63548(15) -0.1019(3) 0.0703(7) Uani 1 1 d . . . . .
H5 H 0.613834 0.640158 -0.182423 0.084 Uiso 1 1 calc R U . . .
C6 C 0.68624(15) 0.58727(13) 0.0813(3) 0.0577(5) Uani 1 1 d . . . . .
H6 H 0.638662 0.559488 0.123960 0.069 Uiso 1 1 calc R U . . .
C7 C 0.74667(12) 0.45258(11) 0.6415(3) 0.0423(4) Uani 1 1 d . . . . .
C8 C 0.83663(13) 0.44590(11) 0.7674(3) 0.0438(4) Uani 1 1 d . . . . .
C9 C 0.84916(12) 0.40077(11) 0.9711(3) 0.0421(4) Uani 1 1 d . . . . .
C10 C 0.93543(13) 0.39687(12) 1.0967(3) 0.0513(5) Uani 1 1 d . . . . .
H10 H 0.983272 0.422074 1.049098 0.062 Uiso 1 1 calc R U . . .
C11 C 0.95049(14) 0.35645(13) 1.2888(3) 0.0575(5) Uani 1 1 d . . . . .
H11 H 1.008203 0.354137 1.371290 0.069 Uiso 1 1 calc R U . . .
C12 C 0.87932(14) 0.31907(12) 1.3595(3) 0.0546(5) Uani 1 1 d . . . . .
H12 H 0.889296 0.291560 1.490051 0.066 Uiso 1 1 calc R U . . .
C13 C 0.79417(13) 0.32230(11) 1.2384(3) 0.0480(5) Uani 1 1 d . . . . .
H13 H 0.747182 0.296606 1.288308 0.058 Uiso 1 1 calc R U . . .
C14 C 0.77612(12) 0.36337(10) 1.0411(3) 0.0415(4) Uani 1 1 d . . . . .
C15 C 0.68534(12) 0.36720(11) 0.9076(3) 0.0426(4) Uani 1 1 d . . . . .
C16 C 0.61182(13) 0.32702(12) 0.9674(3) 0.0547(5) Uani 1 1 d . . . . .
H16 H 0.620537 0.297036 1.094472 0.066 Uiso 1 1 calc R U . . .
C17 C 0.52720(14) 0.33078(14) 0.8430(4) 0.0633(6) Uani 1 1 d . . . . .
H17 H 0.479306 0.303835 0.886392 0.076 Uiso 1 1 calc R U . . .
C18 C 0.51336(14) 0.37464(14) 0.6536(4) 0.0631(6) Uani 1 1 d . . . . .
H18 H 0.455937 0.377866 0.569893 0.076 Uiso 1 1 calc R U . . .
C19 C 0.58429(13) 0.41351(13) 0.5885(3) 0.0553(5) Uani 1 1 d . . . . .
H19 H 0.574456 0.442090 0.459406 0.066 Uiso 1 1 calc R U . . .
C20 C 0.67100(12) 0.41093(11) 0.7127(3) 0.0434(4) Uani 1 1 d . . . . .
N1 N 0.79134(11) 0.53349(10) 0.3882(2) 0.0502(4) Uani 1 1 d . . . . .
H1 H 0.846019 0.528808 0.455970 0.060 Uiso 1 1 calc R U . . .
N2 N 0.72621(10) 0.49608(9) 0.4620(2) 0.0463(4) Uani 1 1 d . . . . .
O1 O 0.90291(9) 0.47785(9) 0.7076(2) 0.0602(4) Uani 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
C1 C6 1.377(3) . ?
C1 C2 1.380(3) . ?
C1 N1 1.404(2) . ?
C2 C3 1.378(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N2 1.325(2) . ?
C7 C8 1.446(3) . ?
C7 C20 1.471(2) . ?
C8 O1 1.251(2) . ?
C8 C9 1.469(2) . ?
C9 C10 1.396(3) . ?
C9 C14 1.405(2) . ?
C10 C11 1.368(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.402(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.472(3) . ?
C15 C16 1.400(2) . ?
C15 C20 1.409(2) . ?
C16 C17 1.372(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.373(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.397(3) . ?
C19 H19 0.9300 . ?
N1 N2 1.316(2) . ?
N1 H1 0.8600 . ?

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
C6 C1 C2 120.23(18) . . ?
C6 C1 N1 121.82(17) . . ?
C2 C1 N1 117.95(19) . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 121.1(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 119.0(2) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
N2 C7 C8 123.89(16) . . ?
N2 C7 C20 116.00(17) . . ?
C8 C7 C20 120.10(15) . . ?
O1 C8 C7 121.70(16) . . ?
O1 C8 C9 119.92(17) . . ?
C7 C8 C9 118.38(15) . . ?
C10 C9 C14 120.29(16) . . ?
C10 C9 C8 118.56(16) . . ?
C14 C9 C8 121.15(17) . . ?
C11 C10 C9 120.84(18) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 119.55(19) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 120.41(18) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 121.65(17) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C9 117.27(17) . . ?
C13 C14 C15 122.61(16) . . ?
C9 C14 C15 120.12(15) . . ?
C16 C15 C20 118.28(18) . . ?
C16 C15 C14 121.67(16) . . ?
C20 C15 C14 120.04(16) . . ?
C17 C16 C15 121.61(18) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 119.83(19) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 120.0(2) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 121.23(19) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C15 119.00(17) . . ?
C19 C20 C7 120.88(16) . . ?
C15 C20 C7 120.12(17) . . ?
N2 N1 C1 120.48(17) . . ?
N2 N1 H1 119.8 . . ?
C1 N1 H1 119.8 . . ?
N1 N2 C7 118.81(16) . . ?

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
C6 C1 C2 C3 1.1(3) . . . . ?
N1 C1 C2 C3 -179.45(17) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
N1 C1 C6 C5 179.57(17) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
N2 C7 C8 O1 -3.8(3) . . . . ?
C20 C7 C8 O1 177.30(16) . . . . ?
N2 C7 C8 C9 175.67(15) . . . . ?
C20 C7 C8 C9 -3.2(2) . . . . ?
O1 C8 C9 C10 1.8(2) . . . . ?
C7 C8 C9 C10 -177.69(16) . . . . ?
O1 C8 C9 C14 -179.22(16) . . . . ?
C7 C8 C9 C14 1.3(2) . . . . ?
C14 C9 C10 C11 0.3(3) . . . . ?
C8 C9 C10 C11 179.25(17) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C9 0.5(3) . . . . ?
C12 C13 C14 C15 179.61(17) . . . . ?
C10 C9 C14 C13 -0.5(2) . . . . ?
C8 C9 C14 C13 -179.41(15) . . . . ?
C10 C9 C14 C15 -179.65(16) . . . . ?
C8 C9 C14 C15 1.4(2) . . . . ?
C13 C14 C15 C16 -2.4(3) . . . . ?
C9 C14 C15 C16 176.77(16) . . . . ?
C13 C14 C15 C20 178.69(16) . . . . ?
C9 C14 C15 C20 -2.2(2) . . . . ?
C20 C15 C16 C17 -1.2(3) . . . . ?
C14 C15 C16 C17 179.87(18) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
C17 C18 C19 C20 -1.1(3) . . . . ?
C18 C19 C20 C15 0.2(3) . . . . ?
C18 C19 C20 C7 179.86(18) . . . . ?
C16 C15 C20 C19 0.9(3) . . . . ?
C14 C15 C20 C19 179.84(16) . . . . ?
C16 C15 C20 C7 -178.76(16) . . . . ?
C14 C15 C20 C7 0.2(2) . . . . ?
N2 C7 C20 C19 3.9(2) . . . . ?
C8 C7 C20 C19 -177.12(17) . . . . ?
N2 C7 C20 C15 -176.47(15) . . . . ?
C8 C7 C20 C15 2.5(2) . . . . ?
C6 C1 N1 N2 -2.8(3) . . . . ?
C2 C1 N1 N2 177.79(16) . . . . ?
C1 N1 N2 C7 -179.25(15) . . . . ?
C8 C7 N2 N1 2.3(2) . . . . ?
C20 C7 N2 N1 -178.78(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.86 1.86 2.543(2) 135.5 . yes

_refine_diff_density_max         0.130
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.027

####################################################################### 
# 
# 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_compound5
_database_code_depnum_ccdc_archive 'CCDC 2223357'
loop_
_audit_author_name
_audit_author_address
'Snehadrinarayan Khatua'
;North Eastern Hill University
India
;
_audit_update_record             
;
2023-07-08 deposited with the CCDC.	2023-07-17 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 H21 N3 O2'
_chemical_formula_weight         359.42

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      tetragonal
_space_group_IT_number           82
_space_group_name_H-M_alt        'I -4'
_space_group_name_Hall           'I -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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'y, -x, -z'
'-y, x, -z'
'-x, -y, z'
'x+1/2, y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'

_cell_length_a                   26.8526(11)
_cell_length_b                   26.8526(11)
_cell_length_c                   5.0570(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3646.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3741
_cell_measurement_theta_min      2.933
_cell_measurement_theta_max      28.293

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.604
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.039
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\^A?S DIAMOND microfocus Mo tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Photon III detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8663
_diffrn_reflns_av_unetI/netI     0.0720
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.145
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_full        24.990
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3190
_reflns_number_gt                2253
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.0562P)²+1.2374P] 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_abs_structure_details 
;
 Flack x determined using 641 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3190
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0681
_refine_ls_wR_factor_ref         0.1502
_refine_ls_wR_factor_gt          0.1363
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS (Version =  20221)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
# Solvent Accessible Volume =       311
# Electrons Found in S.A.V. =        79
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.500 8 0 ' '
2 0.000 0.500 0.580 154 40 ' '
3 0.500 1.000 0.454 154 40 ' '
4 0.500 0.500 0.000 8 0 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
;
A highly disordered water molecule was found 
during refinement. Also, the locatedpositions 
did not show good convergence during refinement. 
Therefore, squeeze routine of PLATON was used to
remove scattering contribution from solvent molecules.
Squeeze results are appended to the cif. A total of 
~10 electrons are removed from asymmetric unit (Z = 8) 
which may correspond to one water molecule. The atoms removed 
through squeeze are shown in the unit cell contents.
;

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 0.22067(13) 0.59616(13) 1.0045(8) 0.0599(11) Uani 1 1 d . . . . .
N1 N 0.28586(15) 0.54075(15) 0.6704(9) 0.0423(11) Uani 1 1 d . . . . .
N2 N 0.23874(16) 0.53174(15) 0.6478(9) 0.0478(11) Uani 1 1 d . . . . .
H2 H 0.218013 0.547750 0.745675 0.057 Uiso 1 1 calc R U . . .
N3 N 0.16200(17) 0.39016(17) -0.0476(11) 0.0618(14) Uani 1 1 d . . . . .
C14 C 0.3254(3) 0.7034(2) 1.5742(12) 0.0644(18) Uani 1 1 d . . . . .
H14 H 0.338148 0.725294 1.699885 0.077 Uiso 1 1 calc R U . . .
C13 C 0.2746(3) 0.6977(2) 1.5523(14) 0.0649(18) Uani 1 1 d . . . . .
H13 H 0.253068 0.715377 1.661161 0.078 Uiso 1 1 calc R U . . .
C12 C 0.2565(2) 0.6650(2) 1.3650(12) 0.0545(15) Uani 1 1 d . . . . .
H12 H 0.222332 0.660865 1.346250 0.065 Uiso 1 1 calc R U . . .
C11 C 0.2889(2) 0.63798(18) 1.2034(11) 0.0446(13) Uani 1 1 d . . . . .
C10 C 0.26777(19) 0.60232(18) 1.0146(12) 0.0449(13) Uani 1 1 d . . . . .
C9 C 0.30064(18) 0.57461(18) 0.8482(11) 0.0387(12) Uani 1 1 d . . . . .
C1 C 0.22080(18) 0.49671(17) 0.4685(11) 0.0425(13) Uani 1 1 d . . . . .
C6 C 0.25104(18) 0.47276(17) 0.2883(10) 0.0402(13) Uani 1 1 d . . . . .
H6 H 0.284895 0.480023 0.283703 0.048 Uiso 1 1 calc R U . . .
C5 C 0.23177(18) 0.43840(18) 0.1160(11) 0.0449(14) Uani 1 1 d . . . . .
H5 H 0.252952 0.422859 -0.003870 0.054 Uiso 1 1 calc R U . . .
C4 C 0.18127(19) 0.42605(19) 0.1152(11) 0.0456(13) Uani 1 1 d . . . . .
C7 C 0.1093(2) 0.3792(2) -0.0487(16) 0.085(2) Uani 1 1 d . . . . .
H7A H 0.090898 0.409016 -0.086196 0.128 Uiso 1 1 calc R U . . .
H7B H 0.099597 0.366517 0.121266 0.128 Uiso 1 1 calc R U . . .
H7C H 0.102293 0.354672 -0.181949 0.128 Uiso 1 1 calc R U . . .
C2 C 0.17095(19) 0.48572(18) 0.4712(12) 0.0506(14) Uani 1 1 d . . . . .
H2A H 0.150319 0.501856 0.591479 0.061 Uiso 1 1 calc R U . . .
C3 C 0.1507(2) 0.4515(2) 0.3005(13) 0.0556(16) Uani 1 1 d . . . . .
H3 H 0.116771 0.444827 0.306437 0.067 Uiso 1 1 calc R U . . .
C15 C 0.3571(2) 0.6781(2) 1.4175(12) 0.0544(16) Uani 1 1 d . . . . .
H15 H 0.391140 0.683187 1.437926 0.065 Uiso 1 1 calc R U . . .
C16 C 0.3407(2) 0.64452(19) 1.2251(11) 0.0439(13) Uani 1 1 d . . . . .
C17 C 0.3740(2) 0.61773(19) 1.0468(11) 0.0464(14) Uani 1 1 d . . . . .
C18 C 0.4260(2) 0.6253(2) 1.0486(13) 0.0576(16) Uani 1 1 d . . . . .
H18 H 0.439614 0.647335 1.170554 0.069 Uiso 1 1 calc R U . . .
C19 C 0.4569(2) 0.6012(2) 0.8778(13) 0.0603(17) Uani 1 1 d . . . . .
H19 H 0.491122 0.606453 0.886116 0.072 Uiso 1 1 calc R U . . .
C20 C 0.4371(2) 0.5688(2) 0.6900(13) 0.0595(16) Uani 1 1 d . . . . .
H20 H 0.457958 0.553079 0.569252 0.071 Uiso 1 1 calc R U . . .
C21 C 0.38691(19) 0.55998(19) 0.6835(11) 0.0452(14) Uani 1 1 d . . . . .
H21 H 0.374007 0.537730 0.560278 0.054 Uiso 1 1 calc R U . . .
C22 C 0.35476(18) 0.58406(17) 0.8598(11) 0.0402(13) Uani 1 1 d . . . . .
C8 C 0.1934(2) 0.3640(2) -0.2296(13) 0.0616(18) Uani 1 1 d . . . . .
H8A H 0.218542 0.346197 -0.133487 0.092 Uiso 1 1 calc R U . . .
H8B H 0.208911 0.387383 -0.347157 0.092 Uiso 1 1 calc R U . . .
H8C H 0.173708 0.340922 -0.330053 0.092 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 C10 1.277(5) . ?
N1 N2 1.293(5) . ?
N1 C9 1.339(6) . ?
N2 C1 1.393(6) . ?
N2 H2 0.8600 . ?
N3 C4 1.369(6) . ?
N3 C8 1.431(7) . ?
N3 C7 1.447(6) . ?
C14 C15 1.346(8) . ?
C14 C13 1.377(8) . ?
C14 H14 0.9300 . ?
C13 C12 1.380(8) . ?
C13 H13 0.9300 . ?
C12 C11 1.396(8) . ?
C12 H12 0.9300 . ?
C11 C16 1.405(7) . ?
C11 C10 1.467(7) . ?
C10 C9 1.428(7) . ?
C9 C22 1.476(6) . ?
C1 C2 1.371(6) . ?
C1 C6 1.379(7) . ?
C6 C5 1.371(7) . ?
C6 H6 0.9300 . ?
C5 C4 1.396(6) . ?
C5 H5 0.9300 . ?
C4 C3 1.420(8) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C2 C3 1.373(7) . ?
C2 H2A 0.9300 . ?
C3 H3 0.9300 . ?
C15 C16 1.398(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.460(7) . ?
C17 C22 1.406(7) . ?
C17 C18 1.412(7) . ?
C18 C19 1.360(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.395(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.368(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.400(7) . ?
C21 H21 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
N2 N1 C9 118.5(4) . . ?
N1 N2 C1 121.5(4) . . ?
N1 N2 H2 119.3 . . ?
C1 N2 H2 119.3 . . ?
C4 N3 C8 120.6(4) . . ?
C4 N3 C7 121.1(5) . . ?
C8 N3 C7 118.3(5) . . ?
C15 C14 C13 121.4(6) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C13 C12 118.4(6) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C13 C12 C11 120.8(6) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C11 C16 120.3(5) . . ?
C12 C11 C10 118.6(5) . . ?
C16 C11 C10 121.0(5) . . ?
O1 C10 C9 121.4(5) . . ?
O1 C10 C11 119.6(5) . . ?
C9 C10 C11 119.0(5) . . ?
N1 C9 C10 124.5(4) . . ?
N1 C9 C22 115.8(5) . . ?
C10 C9 C22 119.7(5) . . ?
C2 C1 C6 118.8(5) . . ?
C2 C1 N2 118.5(5) . . ?
C6 C1 N2 122.8(4) . . ?
C5 C6 C1 120.8(4) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C6 C5 C4 121.9(5) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
N3 C4 C5 122.4(5) . . ?
N3 C4 C3 121.1(5) . . ?
C5 C4 C3 116.4(5) . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 C2 C3 121.6(6) . . ?
C1 C2 H2A 119.2 . . ?
C3 C2 H2A 119.2 . . ?
C2 C3 C4 120.6(5) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C14 C15 C16 122.4(6) . . ?
C14 C15 H15 118.8 . . ?
C16 C15 H15 118.8 . . ?
C15 C16 C11 116.6(5) . . ?
C15 C16 C17 123.7(5) . . ?
C11 C16 C17 119.7(5) . . ?
C22 C17 C18 117.4(5) . . ?
C22 C17 C16 120.5(5) . . ?
C18 C17 C16 122.1(5) . . ?
C19 C18 C17 122.1(5) . . ?
C19 C18 H18 118.9 . . ?
C17 C18 H18 118.9 . . ?
C18 C19 C20 119.7(6) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C21 C20 C19 120.0(6) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 120.8(5) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C17 119.9(5) . . ?
C21 C22 C9 120.2(5) . . ?
C17 C22 C9 119.9(5) . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
C9 N1 N2 C1 -179.5(4) . . . . ?
C15 C14 C13 C12 0.2(9) . . . . ?
C14 C13 C12 C11 0.7(8) . . . . ?
C13 C12 C11 C16 -1.4(8) . . . . ?
C13 C12 C11 C10 177.7(5) . . . . ?
C12 C11 C10 O1 -1.0(7) . . . . ?
C16 C11 C10 O1 178.0(5) . . . . ?
C12 C11 C10 C9 179.9(5) . . . . ?
C16 C11 C10 C9 -1.0(7) . . . . ?
N2 N1 C9 C10 -0.8(7) . . . . ?
N2 N1 C9 C22 -178.6(4) . . . . ?
O1 C10 C9 N1 0.3(8) . . . . ?
C11 C10 C9 N1 179.3(5) . . . . ?
O1 C10 C9 C22 178.0(5) . . . . ?
C11 C10 C9 C22 -3.0(7) . . . . ?
N1 N2 C1 C2 174.2(5) . . . . ?
N1 N2 C1 C6 -6.0(7) . . . . ?
C2 C1 C6 C5 -0.4(7) . . . . ?
N2 C1 C6 C5 179.8(5) . . . . ?
C1 C6 C5 C4 -0.2(8) . . . . ?
C8 N3 C4 C5 -1.0(8) . . . . ?
C7 N3 C4 C5 -178.3(6) . . . . ?
C8 N3 C4 C3 -178.6(5) . . . . ?
C7 N3 C4 C3 4.1(9) . . . . ?
C6 C5 C4 N3 -176.9(5) . . . . ?
C6 C5 C4 C3 0.7(8) . . . . ?
C6 C1 C2 C3 0.3(8) . . . . ?
N2 C1 C2 C3 -179.8(5) . . . . ?
C1 C2 C3 C4 0.2(8) . . . . ?
N3 C4 C3 C2 177.0(5) . . . . ?
C5 C4 C3 C2 -0.8(8) . . . . ?
C13 C14 C15 C16 -0.3(9) . . . . ?
C14 C15 C16 C11 -0.4(8) . . . . ?
C14 C15 C16 C17 178.0(5) . . . . ?
C12 C11 C16 C15 1.2(7) . . . . ?
C10 C11 C16 C15 -177.8(5) . . . . ?
C12 C11 C16 C17 -177.3(5) . . . . ?
C10 C11 C16 C17 3.7(7) . . . . ?
C15 C16 C17 C22 179.3(5) . . . . ?
C11 C16 C17 C22 -2.3(7) . . . . ?
C15 C16 C17 C18 -2.4(8) . . . . ?
C11 C16 C17 C18 175.9(5) . . . . ?
C22 C17 C18 C19 0.0(8) . . . . ?
C16 C17 C18 C19 -178.3(5) . . . . ?
C17 C18 C19 C20 1.3(9) . . . . ?
C18 C19 C20 C21 -2.0(9) . . . . ?
C19 C20 C21 C22 1.4(8) . . . . ?
C20 C21 C22 C17 0.0(7) . . . . ?
C20 C21 C22 C9 179.3(5) . . . . ?
C18 C17 C22 C21 -0.7(7) . . . . ?
C16 C17 C22 C21 177.7(5) . . . . ?
C18 C17 C22 C9 180.0(4) . . . . ?
C16 C17 C22 C9 -1.7(7) . . . . ?
N1 C9 C22 C21 2.9(7) . . . . ?
C10 C9 C22 C21 -175.0(5) . . . . ?
N1 C9 C22 C17 -177.8(4) . . . . ?
C10 C9 C22 C17 4.3(7) . . . . ?

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.037



####################################################################### 
# 
# 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_compound4
_database_code_depnum_ccdc_archive 'CCDC 2223356'
loop_
_audit_author_name
_audit_author_address
'Snehadrinarayan Khatua'
;North Eastern Hill University
India
;
_audit_update_record             
;
2023-07-08 deposited with the CCDC.	2023-07-17 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            'C21 H16 N2 O2'
_chemical_formula_weight         328.36

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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   24.6783(9)
_cell_length_b                   12.9905(4)
_cell_length_c                   5.0465(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1617.82(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3115
_cell_measurement_theta_min      2.233
_cell_measurement_theta_max      28.193

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\^A?S DIAMOND microfocus Mo tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Photon III detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15092
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.276
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_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             2836
_reflns_number_gt                2330
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_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)+(0.0426P)²+0.3054P] 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_abs_structure_details 
;
 Flack x determined using 809 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2836
_refine_ls_number_parameters     227
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1128
_refine_ls_wR_factor_gt          0.1070
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.106
_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
C1 C 0.85266(13) 0.6029(2) -0.0169(8) 0.0453(8) Uani 1 1 d . . . . .
C2 C 0.80906(15) 0.5966(3) -0.1851(8) 0.0516(9) Uani 1 1 d . . . . .
H2 H 0.783482 0.649132 -0.186095 0.062 Uiso 1 1 calc R U . . .
C3 C 0.80256(14) 0.5136(3) -0.3524(9) 0.0511(9) Uani 1 1 d . . . . .
H3 H 0.772527 0.509930 -0.463290 0.061 Uiso 1 1 calc R U . . .
C4 C 0.84044(15) 0.4368(3) -0.3547(8) 0.0502(9) Uani 1 1 d . . . . .
C5 C 0.88501(16) 0.4435(3) -0.1896(9) 0.0631(11) Uani 1 1 d . . . . .
H5 H 0.911078 0.391806 -0.192703 0.076 Uiso 1 1 calc R U . . .
C6 C 0.89120(15) 0.5260(3) -0.0202(9) 0.0586(10) Uani 1 1 d . . . . .
H6 H 0.921167 0.529753 0.091078 0.070 Uiso 1 1 calc R U . . .
C7 C 0.79168(17) 0.3403(3) -0.6749(11) 0.0747(13) Uani 1 1 d . . . . .
H7A H 0.790607 0.396930 -0.796841 0.112 Uiso 1 1 calc R U . . .
H7B H 0.759338 0.340267 -0.569147 0.112 Uiso 1 1 calc R U . . .
H7C H 0.794024 0.276821 -0.771769 0.112 Uiso 1 1 calc R U . . .
C9 C 0.85492(13) 0.8556(3) 0.4896(8) 0.0498(8) Uani 1 1 d . . . . .
C10 C 0.86152(14) 0.9427(3) 0.6728(8) 0.0485(8) Uani 1 1 d . . . . .
C11 C 0.82282(16) 1.0216(3) 0.6683(9) 0.0594(10) Uani 1 1 d . . . . .
H11 H 0.793994 1.017945 0.549968 0.071 Uiso 1 1 calc R U . . .
C12 C 0.82692(17) 1.1043(3) 0.8363(10) 0.0670(11) Uani 1 1 d . . . . .
H12 H 0.801360 1.156816 0.831252 0.080 Uiso 1 1 calc R U . . .
C13 C 0.86977(17) 1.1082(3) 1.0138(10) 0.0664(11) Uani 1 1 d . . . . .
H13 H 0.872526 1.163248 1.131051 0.080 Uiso 1 1 calc R U . . .
C14 C 0.90793(16) 1.0323(3) 1.0182(9) 0.0608(10) Uani 1 1 d . . . . .
H14 H 0.936398 1.037083 1.138268 0.073 Uiso 1 1 calc R U . . .
C15 C 0.90565(14) 0.9469(3) 0.8473(7) 0.0463(8) Uani 1 1 d . . . . .
C16 C 0.94700(13) 0.8655(3) 0.8473(7) 0.0448(8) Uani 1 1 d . . . . .
C17 C 0.99152(15) 0.8669(3) 1.0197(8) 0.0573(10) Uani 1 1 d . . . . .
H17 H 0.994539 0.920104 1.142163 0.069 Uiso 1 1 calc R U . . .
C18 C 1.03071(16) 0.7923(3) 1.0131(9) 0.0618(10) Uani 1 1 d . . . . .
H18 H 1.060199 0.795738 1.127514 0.074 Uiso 1 1 calc R U . . .
C19 C 1.02615(16) 0.7118(3) 0.8352(10) 0.0648(10) Uani 1 1 d . . . . .
H19 H 1.052274 0.660183 0.831820 0.078 Uiso 1 1 calc R U . . .
C20 C 0.98281(15) 0.7080(3) 0.6629(9) 0.0583(10) Uani 1 1 d . . . . .
H20 H 0.980171 0.653900 0.542946 0.070 Uiso 1 1 calc R U . . .
C21 C 0.94292(14) 0.7839(3) 0.6655(8) 0.0455(8) Uani 1 1 d . . . . .
C22 C 0.89659(13) 0.7779(2) 0.4835(8) 0.0445(8) Uani 1 1 d . . . . .
N1 N 0.89593(11) 0.6969(2) 0.3206(7) 0.0462(7) Uani 1 1 d . . . . .
N2 N 0.85586(11) 0.6876(2) 0.1540(7) 0.0498(7) Uani 1 1 d . . . . .
H2A H 0.831071 0.734129 0.148968 0.060 Uiso 1 1 calc R U . . .
O1 O 0.81348(11) 0.8499(2) 0.3445(6) 0.0685(8) Uani 1 1 d . . . . .
O2 O 0.83775(11) 0.35027(19) -0.5071(7) 0.0682(8) Uani 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
C1 C2 1.373(5) . ?
C1 C6 1.379(5) . ?
C1 N2 1.401(4) . ?
C2 C3 1.378(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(5) . ?
C3 H3 0.9300 . ?
C4 O2 1.363(4) . ?
C4 C5 1.383(5) . ?
C5 C6 1.379(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O2 1.424(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C9 O1 1.260(4) . ?
C9 C22 1.441(5) . ?
C9 C10 1.470(5) . ?
C10 C15 1.402(5) . ?
C10 C11 1.402(5) . ?
C11 C12 1.371(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.364(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.406(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.470(5) . ?
C16 C17 1.402(5) . ?
C16 C21 1.405(5) . ?
C17 C18 1.370(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.379(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.393(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.469(5) . ?
C22 N1 1.335(4) . ?
N1 N2 1.304(4) . ?
N2 H2A 0.8600 . ?

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 C1 C6 119.3(3) . . ?
C2 C1 N2 118.1(3) . . ?
C6 C1 N2 122.5(3) . . ?
C1 C2 C3 121.1(3) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
O2 C4 C3 125.0(3) . . ?
O2 C4 C5 115.5(3) . . ?
C3 C4 C5 119.5(3) . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C1 C6 C5 119.6(4) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C9 C22 121.7(3) . . ?
O1 C9 C10 120.0(3) . . ?
C22 C9 C10 118.2(3) . . ?
C15 C10 C11 120.7(4) . . ?
C15 C10 C9 120.7(3) . . ?
C11 C10 C9 118.5(4) . . ?
C12 C11 C10 120.8(4) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 119.0(4) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C14 C13 C12 120.6(4) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 122.2(4) . . ?
C13 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
C10 C15 C14 116.6(3) . . ?
C10 C15 C16 120.7(3) . . ?
C14 C15 C16 122.7(3) . . ?
C17 C16 C21 118.1(3) . . ?
C17 C16 C15 122.3(3) . . ?
C21 C16 C15 119.5(3) . . ?
C18 C17 C16 121.9(4) . . ?
C18 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C17 C18 C19 119.6(4) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C20 C19 C18 119.9(4) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 121.1(4) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C16 119.3(3) . . ?
C20 C21 C22 120.5(3) . . ?
C16 C21 C22 120.2(3) . . ?
N1 C22 C9 123.8(3) . . ?
N1 C22 C21 115.8(3) . . ?
C9 C22 C21 120.4(3) . . ?
N2 N1 C22 118.6(3) . . ?
N1 N2 C1 120.8(3) . . ?
N1 N2 H2A 119.6 . . ?
C1 N2 H2A 119.6 . . ?
C4 O2 C7 116.7(3) . . ?

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
C6 C1 C2 C3 1.5(6) . . . . ?
N2 C1 C2 C3 -178.0(3) . . . . ?
C1 C2 C3 C4 -1.0(6) . . . . ?
C2 C3 C4 O2 178.5(4) . . . . ?
C2 C3 C4 C5 -0.2(6) . . . . ?
O2 C4 C5 C6 -178.0(4) . . . . ?
C3 C4 C5 C6 0.9(6) . . . . ?
C2 C1 C6 C5 -0.8(6) . . . . ?
N2 C1 C6 C5 178.6(4) . . . . ?
C4 C5 C6 C1 -0.4(6) . . . . ?
O1 C9 C10 C15 176.0(4) . . . . ?
C22 C9 C10 C15 -3.6(5) . . . . ?
O1 C9 C10 C11 -4.2(6) . . . . ?
C22 C9 C10 C11 176.2(4) . . . . ?
C15 C10 C11 C12 -0.7(6) . . . . ?
C9 C10 C11 C12 179.6(4) . . . . ?
C10 C11 C12 C13 -0.7(7) . . . . ?
C11 C12 C13 C14 1.3(7) . . . . ?
C12 C13 C14 C15 -0.5(7) . . . . ?
C11 C10 C15 C14 1.4(5) . . . . ?
C9 C10 C15 C14 -178.8(3) . . . . ?
C11 C10 C15 C16 -178.4(4) . . . . ?
C9 C10 C15 C16 1.3(5) . . . . ?
C13 C14 C15 C10 -0.9(6) . . . . ?
C13 C14 C15 C16 179.0(4) . . . . ?
C10 C15 C16 C17 -179.7(3) . . . . ?
C14 C15 C16 C17 0.5(5) . . . . ?
C10 C15 C16 C21 1.7(5) . . . . ?
C14 C15 C16 C21 -178.2(3) . . . . ?
C21 C16 C17 C18 0.6(5) . . . . ?
C15 C16 C17 C18 -178.0(4) . . . . ?
C16 C17 C18 C19 -1.2(6) . . . . ?
C17 C18 C19 C20 1.1(6) . . . . ?
C18 C19 C20 C21 -0.5(6) . . . . ?
C19 C20 C21 C16 -0.1(6) . . . . ?
C19 C20 C21 C22 -179.1(4) . . . . ?
C17 C16 C21 C20 0.0(5) . . . . ?
C15 C16 C21 C20 178.7(3) . . . . ?
C17 C16 C21 C22 179.0(3) . . . . ?
C15 C16 C21 C22 -2.3(5) . . . . ?
O1 C9 C22 N1 2.4(6) . . . . ?
C10 C9 C22 N1 -178.0(3) . . . . ?
O1 C9 C22 C21 -176.7(4) . . . . ?
C10 C9 C22 C21 2.9(5) . . . . ?
C20 C21 C22 N1 -0.2(5) . . . . ?
C16 C21 C22 N1 -179.1(3) . . . . ?
C20 C21 C22 C9 178.9(4) . . . . ?
C16 C21 C22 C9 0.0(5) . . . . ?
C9 C22 N1 N2 1.1(5) . . . . ?
C21 C22 N1 N2 -179.8(3) . . . . ?
C22 N1 N2 C1 -178.6(3) . . . . ?
C2 C1 N2 N1 179.0(3) . . . . ?
C6 C1 N2 N1 -0.4(5) . . . . ?
C3 C4 O2 C7 -0.1(6) . . . . ?
C5 C4 O2 C7 178.7(4) . . . . ?

_refine_diff_density_max         0.124
_refine_diff_density_min         -0.115
_refine_diff_density_rms         0.029

