# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# 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_P-380_a
_database_code_depnum_ccdc_archive 'CCDC 2308691'
loop_
_audit_author_name
_audit_author_address
'Dr. Babulal Das'
;Dibrugarh University
India
;
_audit_update_record             
;
2023-11-17 deposited with the CCDC.	2024-09-02 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            'C16 H15 N3 O'
_chemical_formula_weight         265.31

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.1513(8)
_cell_length_b                   5.6813(6)
_cell_length_c                   14.7970(15)
_cell_angle_alpha                90
_cell_angle_beta                 93.787(3)
_cell_angle_gamma                90
_cell_volume                     683.75(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3437
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      20.49

_exptl_crystal_description       'thin needles'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(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            11528
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.379
_diffrn_reflns_theta_max         21.398
_diffrn_reflns_theta_full        21.398
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1539
_reflns_number_gt                1275
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.991

_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 2018/2 (Sheldrick, 2018)'
_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)+(0.0517P)²+0.2628P] 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 477 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.0(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1539
_refine_ls_number_parameters     182
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1202
_refine_ls_wR_factor_gt          0.1057
_refine_ls_goodness_of_fit_ref   1.076
_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
O1 O 0.8467(6) 0.7657(9) 0.6239(3) 0.0679(13) Uani 1 1 d . . . . .
N002 N 0.4259(6) 0.4741(10) 0.1533(4) 0.0507(14) Uani 1 1 d . . . . .
N003 N 0.5471(6) 0.7846(10) 0.2061(4) 0.0620(15) Uani 1 1 d . . . . .
N004 N 0.4719(7) 0.6929(10) 0.1320(4) 0.0635(16) Uani 1 1 d . . . . .
C005 C 0.1631(7) 0.2788(12) 0.1072(4) 0.0437(15) Uani 1 1 d . . . . .
C006 C 0.5485(7) 0.6243(10) 0.2729(4) 0.0442(16) Uani 1 1 d . . . . .
C007 C 0.6282(7) 0.6692(11) 0.3642(4) 0.0439(16) Uani 1 1 d . . . . .
C008 C 0.7220(7) 0.8691(11) 0.3834(4) 0.0491(17) Uani 1 1 d . . . . .
H008 H 0.734333 0.979313 0.337890 0.059 Uiso 1 1 calc R U . . .
C009 C 0.7975(7) 0.9086(10) 0.4683(4) 0.0478(17) Uani 1 1 d . . . . .
H009 H 0.859849 1.043852 0.479427 0.057 Uiso 1 1 calc R U . . .
C00A C 0.0408(8) 0.4418(11) 0.0836(4) 0.0509(17) Uani 1 1 d . . . . .
H00A H 0.067521 0.581921 0.055560 0.061 Uiso 1 1 calc R U . . .
C00B C 0.7802(7) 0.7457(11) 0.5369(4) 0.0483(17) Uani 1 1 d . . . . .
C00C C -0.1585(8) 0.1923(14) 0.1438(4) 0.058(2) Uani 1 1 d . . . . .
H00C H -0.266942 0.162445 0.156212 0.069 Uiso 1 1 calc R U . . .
C00D C -0.1205(8) 0.3966(13) 0.1014(4) 0.0570(18) Uani 1 1 d . . . . .
H00D H -0.202595 0.504798 0.084685 0.068 Uiso 1 1 calc R U . . .
C00E C 0.3392(7) 0.3221(12) 0.0854(4) 0.0581(19) Uani 1 1 d . . . . .
H00B H 0.396307 0.172613 0.082902 0.070 Uiso 1 1 calc R U . . .
H00E H 0.340624 0.395520 0.026273 0.070 Uiso 1 1 calc R U . . .
C00F C 0.4709(7) 0.4283(12) 0.2398(5) 0.0549(18) Uani 1 1 d . . . . .
H00F H 0.452804 0.289814 0.271120 0.066 Uiso 1 1 calc R U . . .
C00G C 0.6129(8) 0.5076(12) 0.4341(5) 0.0549(18) Uani 1 1 d . . . . .
H00G H 0.550341 0.372405 0.423410 0.066 Uiso 1 1 calc R U . . .
C00H C 0.6888(8) 0.5452(12) 0.5184(4) 0.0568(18) Uani 1 1 d . . . . .
H00H H 0.678464 0.433724 0.563648 0.068 Uiso 1 1 calc R U . . .
C00I C 0.1213(8) 0.0735(12) 0.1493(4) 0.0563(18) Uani 1 1 d . . . . .
H00I H 0.201796 -0.037709 0.165205 0.068 Uiso 1 1 calc R U . . .
C00J C -0.0401(9) 0.0322(12) 0.1680(4) 0.0595(19) Uani 1 1 d . . . . .
H00J H -0.067593 -0.105741 0.197239 0.071 Uiso 1 1 calc R U . . .
C00K C 0.9363(9) 0.9728(14) 0.6479(4) 0.078(2) Uani 1 1 d . . . . .
H00K H 1.029696 0.984553 0.611903 0.116 Uiso 1 1 calc R U . . .
H00L H 0.972901 0.966260 0.710834 0.116 Uiso 1 1 calc R U . . .
H00M H 0.866819 1.107728 0.637160 0.116 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 C00B 1.367(7) . ?
O1 C00K 1.417(8) . ?
N002 C00F 1.333(8) . ?
N002 N004 1.342(7) . ?
N002 C00E 1.470(7) . ?
N003 N004 1.326(7) . ?
N003 C006 1.343(7) . ?
C005 C00I 1.375(9) . ?
C005 C00A 1.388(8) . ?
C005 C00E 1.513(8) . ?
C006 C00F 1.356(8) . ?
C006 C007 1.483(8) . ?
C007 C008 1.388(8) . ?
C007 C00G 1.394(8) . ?
C008 C009 1.379(7) . ?
C009 C00B 1.388(8) . ?
C00A C00D 1.382(8) . ?
C00B C00H 1.379(9) . ?
C00C C00J 1.358(8) . ?
C00C C00D 1.364(9) . ?
C00G C00H 1.371(8) . ?
C00I C00J 1.382(8) . ?

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
C00B O1 C00K 118.1(5) . . ?
C00F N002 N004 110.0(5) . . ?
C00F N002 C00E 129.1(6) . . ?
N004 N002 C00E 120.8(6) . . ?
N004 N003 C006 108.8(5) . . ?
N003 N004 N002 106.9(5) . . ?
C00I C005 C00A 119.0(5) . . ?
C00I C005 C00E 120.1(6) . . ?
C00A C005 C00E 120.9(6) . . ?
N003 C006 C00F 108.1(6) . . ?
N003 C006 C007 122.4(5) . . ?
C00F C006 C007 129.5(6) . . ?
C008 C007 C00G 117.5(6) . . ?
C008 C007 C006 122.0(6) . . ?
C00G C007 C006 120.5(6) . . ?
C009 C008 C007 121.7(6) . . ?
C008 C009 C00B 119.8(6) . . ?
C00D C00A C005 120.3(6) . . ?
O1 C00B C00H 115.6(5) . . ?
O1 C00B C009 125.5(6) . . ?
C00H C00B C009 119.0(6) . . ?
C00J C00C C00D 120.8(6) . . ?
C00C C00D C00A 119.6(6) . . ?
N002 C00E C005 111.7(5) . . ?
N002 C00F C006 106.2(6) . . ?
C00H C00G C007 121.0(6) . . ?
C00G C00H C00B 121.0(6) . . ?
C005 C00I C00J 120.1(6) . . ?
C00C C00J C00I 120.2(6) . . ?

_refine_diff_density_max         0.126
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.038

